JP2000178188A - Ileum type bile acid transporter inhibitor - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain the subject transporter inhibitor having excellent ileum type bile acid transporter inhibiting action and useful as a treating or preventing agent for hyperlipemia and arteriosclerosis by including new benzylamines. SOLUTION: This transporter inhibitor comprises benzylamines of formula I [R1 is a (substituted)6-10C aryl, a (substituted)tetrazolyl or the like; R2 to R4 are each H, a 1-6C alkyl or the like; R5 is a (substituted)6-10C aryl or the like; R6 is a 1-10C alkyl, a (substituted)7-16C aralkyl or the like, e.g. N-(1- phenylethyl)- phenyl-[6-hydroxy-4-methoxy-2-(1H-tetrazol-5-yl) phenyl]methyl}amine as an active ingredient. The compound of formula I is obtained by reacting, e.g. a compound of formula II with a compound of the formula H2N-R6 in an inert solvent to provide a compound of formula III, reducing the compound of formula III in the inert solvent and removing a preventing group for amino group of the resultant compound.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention relates to an excellent ileal bile acid transporter inhibitor and a therapeutic or preventive agent for hyperlipidemia and arteriosclerosis.

[0002]

2. Description of the Related Art Hyperlipidemia is one of the three major risk factors for ischemic heart disease. In particular, reducing high blood cholesterol levels is useful for treating or preventing ischemic heart disease. Widely accepted. As currently available therapeutic agents for hyperlipidemia, for example, HMG-CoA reductase inhibitors and ion exchange resins are known, and these agents are used for treating or preventing hyperlipidemia and arteriosclerosis. [Am. J. Cardiol., 76, 899-905 (199
Five)].

[0003] HMG-CoA reductase inhibitors have an inhibitory effect on cholesterol synthesis and LDL (low depletion) in the liver.
(Science, 232, 34 (1986)), and the efficacy and safety of these drugs have been widely recognized. Have been used in patients.

[0004] Anion exchange resins also adsorb bile acids and prevent reabsorption of bile acids in the intestine, thereby promoting the conversion of cholesterol to bile acids in the liver, and consequently lowering the blood cholesterol concentration. N. Engl. J. Med., 302, 1219-
1222 (1980)]. As such an anion exchange resin,
For example, the method of using cholestyramine has already been put to practical use, and it is difficult to absorb the drug into the body. ing. However, cholestyramine has the drawbacks that it is extremely difficult for patients to take because cholestyramine has an extremely large dose per dose, and furthermore, a rough feel of the resin when taken is left in the mouth. In addition, the anion exchange resin also adsorbs and discharges certain vitamins, minerals, drugs, etc.
There are many problems.

In recent years, a protein has been cloned that acts in the first step of bile acid reabsorption in the ileum, an ileal bile acid transporter [Wong MH et al., J. Bio.
l. Chem., 269, 1340-1347 (1994)]. It is thought that inhibiting the ileal bile acid transporter activity can provide the same pharmacological effect as cholestyramine.In this context, attempts have been made to find an ileal bile acid transporter inhibitor. [Wes G. et al., J. Me
d. Chem., 37, 873-875 (1994)].

The compounds having the same structure as the compound (I) contained as an active ingredient of the ileal bile acid transporter inhibitor of the present invention are disclosed in JP-A-2-49771 and JP-A-2-101064. There are gazettes, and the above two gazettes disclose compounds having the following general formula (II).

[0007]

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[Wherein, R ³ , R ⁴ and R ⁵ each independently represent a hydrogen atom, a C ₁ -C ₄ alkyl group or a phenyl group, R ⁶ and R ⁷ each independently represent a hydrogen atom, halogen atom, C ₁ -C ₈ alkyl group, C ₃ -
C ₆ cycloalkyl group, C ₂ -C ₄ alkoxyalkyl group, C ₁ -C ₄ alkoxy groups, C ₁ -C ₄ haloalkoxy group, a nitro group, a trifluoromethyl group, a phenyl group,
Benzyl group, phenoxy group, benzyloxy group, C _1-
C ₄ alkylamino group, C ₂ -C ₈ dialkylamino group, cyano group, C ₂ -C ₆ alkylaminocarbonyl group, C ₃ -C ₁₁ dialkylaminocarbonyl group, piperidinocarbonyl group, morpholinocarbonyl group, trimethylsilyl group shows the C ₁ -C ₄ alkylthio group, C ₁ -C ₄ alkylsulfinyl group or a C ₁ -C ₄ alkylsulfonyl group,. ].

[0009] However, the above two publications do not specifically disclose any compound having the same or similar structure as that of the compound (I) of the present invention. Further, the above compound (II) is disclosed as an intermediate of pyrazole carboxylic acid amides disclosed as insecticides, and comprises a bile acid transporter inhibitor or a therapeutic agent for hyperlipidemia and arteriosclerosis. Or, the use as a prophylactic agent is neither described nor suggested.

[0010]

SUMMARY OF THE INVENTION The inventors of the present invention have conducted intensive studies on the synthesis of a series of benzylamines and their pharmacological actions over many years, and as a result, it has been found that benzylamines are superior in ileal bile acid transporters. It has been found that it has an inhibitory effect and is useful as a therapeutic or preventive agent for hyperlipidemia and arteriosclerosis, and has completed the present invention.

[0011]

The bile acid transporter inhibitor of the present invention contains a compound having the general formula (I) or a pharmacologically acceptable salt thereof as an active ingredient.

[0012]

Embedded image

In the above formula, R ¹ is a C ₆ -C ₁₀ aryl group substituted by 1 to 3 groups selected from a substituent group α,
A tetrazolyl group, a (C ₃ -C ₆ cycloalkyl) carbamoyl group, a (C ₁ -C ₆ alkyl) sulfonylcarbamoyl group, and a substituent group δ which may be substituted with a group selected from the substituent group β. May be substituted with 1 to 3 groups (C ₆ -C ₁₀ aryl) sulfonylcarbamoyl group, sulfo group, C ₁ -C ₆ alkylsulfonyl group, 1 to 3 groups substituted with a group selected from substituent group β A C ₆ -C ₁₀ arylsulfonyl group, mono- (C ₁ -C _1
6- alkyl) aminosulfonyl group, di- (C ₁ -C ₆ alkyl) aminosulfonyl group, C ₁ -C ₆ alkylsulfinyl group, and one or three C-substituents which may be substituted with a group selected from substituent group β. _{7 to} C ₁₁ arylcarbonylamino group, a tetrazolylcarbonylamino group which may be substituted with a group selected from substituent group β, or 1 to 3 substituents which may be substituted with a group selected from substituent group β (C ₆ -C ₁₀
Aryl) sulfonylcarbamoylamino group;
² , R ³ and R ⁴ are the same or different and are each a hydrogen atom, a C ₁ -C ₆ alkyl group, a C ₁ -C ₆ alkoxy group,
Hydroxyl group, halogen atom, amino group, mono- (C ₁ -C ₆
Alkyl) amino group or di- (C ₁ -C ₆ alkyl)
Represents an amino group, and R ⁵ is a C ₆ -C ₁₀ aryl group which may be substituted with 1 to 3 groups selected from substituent group β or 1 to 3 groups selected from substituent group β. A thienyl, pyrrolyl, 1,1-dioxothienyl, thiazolyl or oxazolyl group, which may be substituted or condensed with a benzene ring, wherein R ⁶ is a C ₁ -C ₁₀ alkyl group, ^{7 wherein} W is a single bond or C ₁ -C
₆ represents an alkylene group; R ⁷ represents a C ₃ -C ₆ cycloalkyl group which may be substituted by 1 to 3 groups selected from the substituent group γ and may be condensed with a benzene ring. Or a C ₇ -C ₁₆ aralkyl group which may be substituted by 1 to 3 groups with a group having the above formula or a group selected from the substituent group γ.

<Substituent group α> A tetrazolyl group, a sulfo group, a C ₁ group which may be substituted with a group selected from the substituent group β
A C ₆ alkylsulfonyl group, a C ₁ -C ₆ alkylsulfonylamino group and a group selected from the substituent group β.
And up to 3 optionally substituted C ₆ -C ₁₀ arylsulfonylamino groups. <Substituent group β> A C ₁ -C ₆ alkyl group, a C ₁ -C ₆ alkoxy group and a halogen atom. <Substituent group γ> C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halogen atom and formula -ZR ⁸ [wherein, Z
Is a single bond or C ₁ -C ₆ alkylene group, R ⁸
The carboxy group, C ₂ -C ₇ alkoxycarbonyl group, a carbamoyl group, a mono - (C ₁ -C ₆ alkyl) carbamoyl group, di - (C ₁ -C ₆ alkyl) carbamoyl group, C ₁ -C ₆ alkylsulfonyl Group or hydroxyl group. A group having the formula: <Substituent group δ> A C ₁ -C ₆ alkyl group, a C ₁ -C ₆ alkoxy group, a halogen atom and a phenyl group which may be substituted with 1 to 3 groups selected from a substituent group β.

In the definition of R ¹ , “C ₆ -C substituted by 1 to 3 groups selected from the substituent group α”
The C ₆ -C ₁₀ aryl portion of the “ ₁₀ aryl group” has 6 carbon atoms.
And represents 10 to 10 aromatic hydrocarbon groups, for example, phenyl, indenyl, and naphthyl groups, and is preferably a phenyl group.

In the above, the term "C ₁ -C ₆ alkyl group" in the definition of the substituent groups β and δ indicates a straight-chain or branched-chain alkyl group having 1 to 6 carbon atoms. , Ethyl, propyl, isopropyl, butyl, isobutyl, s-butyl, t-butyl, pentyl, isopentyl, 2-methylbutyl, neopentyl, 1-ethylpropyl, hexyl, 4-methylpentyl, 3-methylpentyl, 2-methylpentyl , 1-methylpentyl, 3,
3-dimethylbutyl, 2,2-dimethylbutyl, 1,1
-Dimethylbutyl, 1,2-dimethylbutyl, 1,3-
Dimethylbutyl, 2,3-dimethylbutyl, 2-ethylbutyl group, preferably a C ₁ -C ₄ alkyl group, more preferably a C ₁ -C ₂ alkyl group, particularly preferably a methyl group It is.

In the above, the “C ₁ -C ₆ alkoxy group” in the definition of the substituent groups β and δ is the above-mentioned C ₁ -C ₆
Represents a group in which an oxygen atom is bonded to an alkyl group; for example, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, s-butoxy, t-butoxy, pentoxy, isopentoxy, 2-methylbutoxy, neopentoxy, 1-ethylpropoxy , Hexyloxy,
4-methylpentoxy, 3-methylpentoxy, 2-methylpentoxy, 1-methylpentoxy, 3,3-dimethylbutoxy, 2,2-dimethylbutoxy, 1,1-dimethylbutoxy, 1,2-dimethyl Butoxy, 1,3-
Dimethylbutoxy, 2,3-dimethylbutoxy, 2-ethylbutoxy, preferably C ₁ -C ₄ alkoxy, more preferably C ₁ -C ₂ alkoxy, and particularly preferably methoxy. Group.

In the above, the "halogen atom" in the definition of the substituent groups β and δ is, for example, a fluorine atom, a chlorine atom, a bromine atom or an iodine atom, preferably a fluorine atom or a chlorine atom. is there.

In the above, the "tetrazolyl group which may be substituted with a group selected from the substituent group β" in the definition of the substituent groups α and R ¹ is, for example, 1H-tetrazol-5 -Yl, 1-methyltetrazol-5-yl, 1-
Ethyltetrazol-5-yl, 1-methoxytetrazol-5-yl, 1-ethoxytetrazol-5-yl, 1-fluorotetrazol-5-yl, 1-chlorotetrazol-5-yl group. R ¹ is preferably C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy,
A tetrazolyl group which may be substituted with a group selected from a substituent group consisting of a fluorine atom and a chlorine atom (hereinafter referred to as a substituent group β1), more preferably C ₁ -C ₂ alkyl, C ₁ -C ₂ alkoxy, substituent group consisting of fluorine and chlorine atoms are substituted with a group selected from (hereinafter, referred to. substituent group .beta.2) is also good tetrazolyl group, more preferably methyl, methoxy, A tetrazolyl group which may be substituted with a group selected from a substituent group consisting of a fluorine atom and a chlorine atom (hereinafter referred to as a substituent group β3), particularly preferably a 1H-tetrazol-5-yl group It is. The substituent group α is preferably a tetrazolyl group optionally substituted with a group selected from the substituent group β2, and more preferably a tetrazolyl group substituted with a group selected from the substituent group β3. And particularly preferably a 1H-tetrazol-5-yl group.

In the above, the "C ₁ -C ₆ alkylsulfonyl group" in the definition of R ^{8 in} the substituent groups α and R ¹ and the substituent group γ means that the above C ₁ -C ₆ alkyl group is sulfonyl. Represents a group having a group bonded thereto, for example, methylsulfonyl, ethylsulfonyl, propylsulfonyl, isopropylsulfonyl, butylsulfonyl, isobutylsulfonyl,
s-butylsulfonyl, t-butylsulfonyl, pentylsulfonyl, isopentylsulfonyl, 2-methylbutylsulfonyl, neopentylsulfonyl, 1-ethylpropylsulfonyl, hexylsulfonyl, 4-methylpentylsulfonyl, 3-methylpentylsulfonyl,
2-methylpentylsulfonyl, 1-methylpentylsulfonyl, 3,3-dimethylbutylsulfonyl, 2,2
-Dimethylbutylsulfonyl, 1,1-dimethylbutylsulfonyl, 1,2-dimethylbutylsulfonyl, 1,
3-dimethylbutylsulfonyl, 2,3-dimethylbutylsulfonyl, and 2-ethylbutylsulfonyl groups.
In the substituent group α, it is preferably a C ₁ -C ₄ alkylsulfonyl group, more preferably methylsulfonyl,
It is an ethylsulfonyl, propylsulfonyl or butylsulfonyl group, more preferably a methylsulfonyl or ethylsulfonyl group, particularly preferably a methylsulfonyl group. In R ¹ , preferably C ₁ -C
₄ alkylsulfonyl group, more preferably methylsulfonyl, ethylsulfonyl, propylsulfonyl or butylsulfonyl group, more preferably methylsulfonyl, ethylsulfonyl or butylsulfonyl group, particularly preferably methylsulfonyl Or an ethylsulfonyl group. R ⁸ in the substituent group γ is preferably a C ₁ -C ₄ alkylsulfonyl group.

In the above, the "C ₁ -C ₆ alkylsulfonylamino group" in the definition of the substituent group α is a group in which an amino group is bonded to _one C ₁ -C ₆ alkylsulfonyl group. Shows, for example, methylsulfonylamino, ethylsulfonylamino, propylsulfonylamino, isopropylsulfonylamino, butylsulfonylamino,
Isobutylsulfonylamino, s-butylsulfonylamino, t-butylsulfonylamino, pentylsulfonylamino, isopentylsulfonylamino, 2-methylbutylsulfonylamino, neopentylsulfonylamino, 1-ethylpropylsulfonylamino, hexylsulfonylamino, 4- Methylpentylsulfonylamino, 3-methylpentylsulfonylamino, 2-methylpentylsulfonylamino, 1-methylpentylsulfonylamino, preferably methylsulfonylamino or ethylsulfonylamino, and particularly preferably methylsulfonyl It is an amino group.

In the above, the C ₆ -C ₁₀ arylsulfonylamino group which may be substituted by 1 to 3 substituents selected from the substituent group β in the definition of the substituent group α. ₆ -C ₁₀ arylsulfonylamino moiety, one C
₆ -C (indicates the C ₆ -C ₁₀ aryl group a sulfonyl group is bonded to the group, for example, phenylsulfonyl, indenyl sulfonyl, naphthylsulfonyl a group.) ₁₀ arylsulfonyl group an amino group is bonded to the group For example, it is a phenylsulfonylamino, indenylsulfonylamino, naphthylsulfonylamino group, and preferably a phenylsulfonylamino group. In addition, one to three substituents (preferably one) selected from the substituent group β are preferably groups selected from the substituent group β2. Such a “C ₆ -C ₁₀ arylsulfonylamino group optionally substituted by 1 to 3 groups selected from the substituent group β” is, for example, phenylsulfonylamino, 2-methylphenylsulfonylamino, Methylphenylsulfonylamino, 4-methylphenylsulfonylamino, 2-methoxyphenylsulfonylamino,
3-methoxyphenylsulfonylamino, 4-methoxyphenylsulfonylamino, 2-fluorophenylsulfonylamino, 3-fluorophenylsulfonylamino, 4-fluorophenylsulfonylamino, 2-chlorophenylsulfonylamino, 3-chlorophenylsulfonylamino, 4-chlorophenyl Sulfonylamino,
(Indan-1-yl) sulfonylamino, (indan-2-yl) sulfonylamino, (naphthalen-1-yl) sulfonylamino, (naphthalen-2-yl) sulfonylamino, preferably the substituent group A phenylsulfonylamino group which may be substituted with a group selected from β2, and particularly preferably a phenylsulfonylamino group.

In the definition of R ¹ , “C ₆ -C 1 to 3 substituted by a group selected from substituent group α”
The substituent group α of the “ ₁₀ aryl group” is preferably a tetrazolyl group, a sulfo group, a C ₁ -C ₄ alkylsulfonyl group, a methylsulfonylamino group which may be substituted with a group selected from the substituent group β2. And a group selected from the group consisting of an ethylsulfonylamino group and a phenylsulfonylamino group which may be substituted with a group selected from the substituent group β2 (hereinafter, referred to as a substituent group α1), and more preferably. Is selected from the group consisting of a tetrazolyl group, a methylsulfonyl group, an ethylsulfonyl group, a propylsulfonyl group, a butylsulfonyl group, a methylsulfonylamino group and a phenylsulfonylamino group which may be substituted with a group selected from the substituent group β3. A 1H-tetrazol-5-yl group, a methylsulfonyl group, and an ethyl group. And is particularly preferably a methylsulfonyl group.

Specific examples of such a “C ₆ -C ₁₀ aryl group substituted by 1 to 3 groups selected from the substituent group α” include, for example, 2-, 3- or 4- (1H- Tetrazol-5-yl) phenyl, 2-, 3- or 4
-(1-methyltetrazol-5-yl) phenyl, 2
-, 3- or 4- (1-ethyltetrazole-5
Yl) phenyl, 2-, 3- or 4- (1-methoxytetrazol-5-yl) phenyl, 2-, 3- or 4- (1-ethoxytetrazol-5-yl) phenyl, 2-, 3- or 4- (1-fluorotetrazol-5-yl) phenyl, 2-, 3- or 4-
(1-chlorotetrazol-5-yl) phenyl, 2
-, 3- or 4-sulfophenyl, 2-, 3- or 4-methylsulfonylphenyl, 2-, 3- or 4-ethylsulfonylphenyl, 2-, 3- or 4-propylsulfonylphenyl, 2-, 3 -Or 4-isopropylsulfonylphenyl, 2-, 3- or 4-butylsulfonylphenyl, 2-, 3- or 4-isobutylsulfonylphenyl, 2-, 3- or 4-s-butylsulfonylphenyl, 2-, 3 -Or 4-t-butylsulfonylphenyl, 2- or 4-pentylsulfonylphenyl, 2- or 4-
Isopentylsulfonylphenyl, 2- or 4-
(2-methylbutylsulfonyl) phenyl, 2- (1-
Ethylpropylsulfonyl) phenyl, 2- or 4
-Hexylsulfonylphenyl, 2-, 3- or 4
-(Methylsulfonylamino) phenyl, 2-, 3- or 4- (ethylsulfonylamino) phenyl, 2
-, 3- or 4- (propylsulfonylamino) phenyl, 2- or 4- (isopropylsulfonylamino) phenyl, 2- or 4- (butylsulfonylamino) phenyl, 2- or 4- (isobutylsulfonylamino) phenyl, 2- or 4- (s-butylsulfonylamino) phenyl, 2- or 4- (t
-Butylsulfonylamino) phenyl, 2-, 3- or 4- (phenylsulfonylamino) phenyl, 2
-, 3- or 4- (2-methylphenylsulfonylamino) phenyl, 2-, 3- or 4- (3-methylphenylsulfonylamino) phenyl, 2-, 3- or 4- (4-methylphenylsulfonylamino) ) Phenyl, 2-, 3- or 4- (2-methoxyphenylsulfonylamino) phenyl, 2-, 3- or 4
-(3-methoxyphenylsulfonylamino) phenyl, 2-, 3- or 4- (4-methoxyphenylsulfonylamino) phenyl, 2-, 3- or 4-
(2-fluorophenylsulfonylamino) phenyl,
2-, 3- or 4- (3-fluorophenylsulfonylamino) phenyl, 2-, 3- or 4- (4-
Fluorophenylsulfonylamino) phenyl, 2-,
3- or 4- (2-chlorophenylsulfonylamino) phenyl, 2-, 3- or 4- (3-chlorophenylsulfonylamino) phenyl, 2-, 3- or 4- (4-chlorophenylsulfonylamino) phenyl, 2, 4-di- (methylsulfonyl) phenyl, 2,
4-di- (ethylsulfonyl) phenyl, 2,4,6-
Tri- (methylsulfonyl) phenyl, 2-, 3- or 4- (1H-tetrazol-5-yl) indenyl, 2- or 4- (1-methyltetrazol-5)
Yl) indenyl, 2-sulfoindenyl, 2-, 3-
Or 4-methylsulfonylindenyl, 2-, 3-
Or 4-ethylsulfonylindenyl, 2- or 4-propylsulfonylindenyl, 2-, 3- or 4- (methylsulfonylamino) indenyl,
-, 3- or 4- (ethylsulfonylamino) indenyl, 3- or 4- (phenylsulfonylamino) indenyl, 2-, 3- or 4- (1H-tetrazol-5-yl) naphthyl, 2- or 4- (1
-Methyltetrazol-5-yl) naphthyl, 2-sulfonaphthyl, 2-, 3- or 4-methylsulphonylnaphthyl, 2-, 3- or 4-ethylsulphonylnaphthyl, 2- or 4-propylsulphonylnaphthyl, 2- , 3- or 4- (methylsulfonylamino) naphthyl, 2-, 3- or 4- (ethylsulfonylamino) naphthyl, 3- or 4- (phenylsulfonylamino) naphthyl, and preferably 2-,
3- or 4- (1H-tetrazol-5-yl) phenyl, 2-, 3- or 4- (1-methyltetrazol-5-yl) phenyl, 2-, 3- or 4-
(1-methoxytetrazol-5-yl) phenyl, 2
-, 3- or 4- (1-fluorotetrazole-5
-Yl) phenyl, 2-, 3- or 4- (1-chlorotetrazol-5-yl) phenyl, 2-, 3- or 4-methylsulfonylphenyl, 2-, 3- or 4-ethylsulfonylphenyl, 2 -, 3- or 4-propylsulfonylphenyl, 2-, 3- or 4-butylsulfonylphenyl, 2-, 3- or 4
-Methylsulfonylaminophenyl or 2-, 3- or 4-phenylsulfonylaminophenyl group, more preferably 2-, 3- or 4- (1H-tetrazol-5-yl) phenyl, 2-, 3 -Or 4-methylsulfonylphenyl, 2-, 3- or 4
-Ethylsulfonylphenyl group, particularly preferably,
2-methylsulfonylphenyl, 3-methylsulfonylphenyl or 4-methylsulfonylphenyl group.

[0025] The above At a, in the definition of R ¹ '(C ₃
—C ₆ cycloalkyl) carbamoyl group ”is a C ₃ -C 6
₆ represents a group in which a carbamoyl group is bonded to a cycloalkyl group (a saturated cyclic hydrocarbon group having 3 to 6 carbon atoms, which is a cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl group), such as cyclopropylcarbamoyl or cyclopropyl butylcarbamoyl, cyclopentylcarbamoyl, a cyclohexylcarbamoyl group, preferably a C ₅ -C ₆ cycloalkylene alkylcarbamoyl group.

[0026] The above-mentioned At a, in the definition of R ¹ "(C ₁
“—C ₆ alkyl) sulfonylcarbamoyl group” refers to a group in which one carbamoyl group is bonded to _one C ₁ -C ₆ alkylsulfonyl group, for example, methylsulfonylcarbamoyl, ethylsulfonylcarbamoyl, propylsulfonylcarbamoyl, isopropylsulfonylcarbamoyl. Butylsulfonylcarbamoyl, isobutylsulfonylcarbamoyl, s-butylsulfonylcarbamoyl, t-butylsulfonylcarbamoyl, pentylsulfonylcarbamoyl, isopentylsulfonylcarbamoyl, 2-methylbutylsulfonylcarbamoyl, neopentylsulfonylcarbamoyl, 1-ethylpropylsulfonylcarbamoyl, hexyl Sulfonylcarbamoyl, 4-methylpentylsulfonylcarbamoyl,
3-methylpentylsulfonylcarbamoyl, 2-methylpentylsulfonylcarbamoyl, 1-methylpentylsulfonylcarbamoyl, 3,3-dimethylbutylsulfonylcarbamoyl, 2,2-dimethylbutylsulfonylcarbamoyl, 1,1-dimethylbutylsulfonylcarbamoyl, 1, 2-dimethylbutylsulfonylcarbamoyl, 1,3-dimethylbutylsulfonylcarbamoyl, 2,3-dimethylbutylsulfonylcarbamoyl, 2-ethylbutylsulfonylcarbamoyl, preferably (C ₁ -C ₄ alkylsulfonyl) carbamoyl; And particularly preferably a (C ₁ -C ₂ alkylsulfonyl) carbamoyl group.

In the above, in the definition of R ¹ , “(C ₆ -C ₁₀ aryl) sulfonylcarbamoyl group which may be substituted by 1 to 3 groups selected from substituent group δ” C ₆ -C ₁₀ aryl) sulfonylcarbamoyl moiety is
And a group in which a carbamoyl group is bonded to the C ₆ -C ₁₀ arylsulfonyl group. In addition, the above (C ₆ −
C ₁₀ aryl) Sulfonylcarbamoyl group substituent group δ
1 to 3 substituents (preferably 1) selected from the group consisting of the C ₁ -C ₆ alkyl group and the C ₁ -C ₆
A phenyl group which may be substituted by 1 to 3 (preferably 1) with an alkoxy group, the halogen atom or a group selected from the substituent group β, preferably C ₁ -C
It is selected from the group consisting of a ₄ alkyl group, a C ₁ -C ₄ alkoxy group, a halogen atom and a phenyl group which may be substituted with a group selected from the aforementioned substituent group β1 (hereinafter referred to as a substituent group δ1). And more preferably C ₁ -C ₂
A group consisting of an alkyl group, a C ₁ -C ₂ alkoxy group, a fluorine atom, a chlorine atom and a phenyl group which may be substituted with a group selected from the above-mentioned substituent group β 2 (hereinafter referred to as a substituent group δ
Two. ), More preferably,
Substituent group consisting of methyl, methoxy, fluorine atom, chlorine atom and optionally substituted phenyl group (the substituent is a C ₁ -C ₂ alkyl, methoxy, fluorine atom or chlorine atom) (hereinafter referred to as substituent group δ3 ), And particularly preferably a substituent group consisting of a methyl group, a phenyl group and a methylphenyl group (hereinafter referred to as a substituent group δ4).
That. ).

One to three substituents such as those selected from the group of substituents δ may be substituted (C ₆ -C ₁₀ aryl)
“Sulfonylcarbamoyl group” is, for example, phenylsulfonylcarbamoyl, 2-, 3- or 4-methylphenylsulfonylcarbamoyl, 2-, 3- or 4
-Ethylphenylsulfonylcarbamoyl, 2-, 3-
Or 4-methoxyphenylsulfonylcarbamoyl, 2-, 3- or 4-fluorophenylsulfonylcarbamoyl, 2-, 3- or 4-chlorophenylsulfonylcarbamoyl, 2-, 3- or 4-
(2-, 3- or 4-methylphenyl) phenylsulfonylcarbamoyl, 2-, 3- or 4- (2
-, 3- or 4-ethylphenyl) phenylsulfonylcarbamoyl, 2-, 3- or 4- (2-, 3
-Or 4-methoxyphenyl) phenylsulfonylcarbamoyl, 2-, 3- or 4- (2-, 3- or 4-fluorophenyl) phenylsulfonylcarbamoyl, 2-, 3- or 4- (2-, 3- or 4-chlorophenyl) phenylsulfonylcarbamoyl, 5-methylinden-1-yl, 5-methylinden-2-yl, 5-methylnaphthalen-1-yl, 5-
A methylnaphthalen-2-yl group, preferably a phenylsulfonylcarbamoyl group which may be substituted with a group selected from the substituent group δ1, and more preferably a group selected from the substituent group δ2. A phenylsulfonylcarbamoyl group which may be substituted with, more preferably a phenylsulfonylcarbamoyl group which may be substituted with a group selected from the substituent group δ3, and particularly preferably It is a phenylsulfonylcarbamoyl group which may be substituted with a selected group.

In the above description, in the definition of R ¹ , “C 1-3 which may be substituted by 1 to 3 groups selected from the substituent group β”
C ₆ -C ₁₀ arylsulfonyl moiety of ₆ -C ₁₀ arylsulfonyl group ", said C ₆ -C ₁₀ indicates the same meaning as an arylsulfonyl group, preferably a phenylsulfonyl group. The one to three substituents (preferably one) selected from the substituent group β are preferably groups selected from the substituent group β1, and more preferably the substituents It is a group selected from the group β2, particularly preferably a group selected from the substituent group β3.

The “C ₆ -C ₁₀ arylsulfonyl group optionally substituted by 1 to 3 groups selected from the substituent group β” is, for example, phenylsulfonyl, 2-, 3
-Or 4-methylphenylsulfonyl, 2-, 3-
Or 4-ethylphenylsulfonyl, 2-, 3- or 4-methoxyphenylsulfonyl, 2-, 3- or 4-fluorophenylsulfonyl, 2-, 3- or 4-chlorophenylsulfonyl, (indene-1
-, 2- or 3-yl) sulfonyl and (naphthalen-1- or 2-yl) sulfonyl groups, preferably a phenylsulfonyl group optionally substituted with a group selected from the substituent group β1. And further preferably a phenylsulfonyl group optionally substituted with a group selected from the substituent group β2, and more preferably a phenylsulfonyl group optionally substituted with a group selected from the substituent group β3. And particularly preferably a phenylsulfonyl group.

[0031] The above-mentioned At a, in the definition of R ¹ "mono -
(C ₁ -C ₆ alkyl) aminosulfonyl group "is mono - (C ₁ -C ₆ alkyl) amino group (one of the C ₁ -
A group in which an amino group is bonded to a C ₆ alkyl group, such as methylamino, ethylamino, propylamino, isopropylamino, butylamino, isobutylamino,
s-butylamino, t-butylamino, pentylamino and hexylamino groups. ) Shows a group having a sulfonyl group bonded thereto, for example, methylaminosulfonyl, ethylaminosulfonyl, propylaminosulfonyl, isopropylaminosulfonyl, butylaminosulfonyl,
Isobutylaminosulfonyl, s-butylaminosulfonyl, t-butylaminosulfonyl, pentylaminosulfonyl, hexylaminosulfonyl, preferably methylaminosulfonyl or ethylaminosulfonyl.

[0032] The above At a, in the definition of R ¹ "di -
(C ₁ -C ₆ alkyl) aminosulfonyl group ”is a di-
(C ₁ -C ₆ alkyl) amino group (same or different 2
C ₁ -C ₆ alkyl groups are bonded to an amino group, for example, dimethylamino, diethylamino, N
-Ethyl-N-methylamino, dipropylamino, diisopropylamino, N-methyl-N-propylamino,
Dibutylamino, diisobutylamino, di-s-butylamino, di-t-butylamino, dipentylamino, N
-Ethyl-N-propylamino, dihexylamino group. ) Shows a group having a sulfonyl group bonded, for example,
Dimethylaminosulfonyl, diethylaminosulfonyl, N-ethyl-N-methylaminosulfonyl, dipropylaminosulfonyl, diisopropylaminosulfonyl, N-methyl-N-propylaminosulfonyl, dibutylaminosulfonyl, diisobutylaminosulfonyl, di-s-butylamino Sulfonyl, di-t-butylaminosulfonyl, dipentylaminosulfonyl, N-
It is an ethyl-N-propylaminosulfonyl or dihexylaminosulfonyl group, preferably a dimethylaminosulfonyl group or a diethylaminosulfonyl group.

[0033] The above At a, in the definition of R ¹ 'C ₁ -
C ₆ alkylsulfinyl group "refers to the C ₁ -C ₆ group sulfinyl group is attached to an alkyl group, for example,
Methylsulfinyl, ethylsulfinyl, propylsulfinyl, isopropylsulfinyl, butylsulfinyl, isobutylsulfinyl, s-butylsulfinyl, t-butylsulfinyl, pentylsulfinyl, isopentylsulfinyl, 2-methylbutylsulfinyl, neopentylsulfinyl, 1-ethylpropylsulfinyl Hexylsulfinyl, 4-methylpentylsulfinyl, 3-methylpentylsulfinyl, 2-methylpentylsulfinyl, 1-methylpentylsulfinyl, 3,3-dimethylbutylsulfinyl, 2,2-dimethylbutylsulfinyl, 1,1-dimethylbutyl Sulfinyl, 1,2-dimethylbutylsulfinyl, 1,3-dimethylbutylsulfinyl,
2,3-dimethyl-butylsulfinyl, 2-ethylbutyl sulfinyl group, preferably a C ₁ -C ₄ alkylsulfinyl group, particularly preferably a C ₁ -C ₂ alkylsulfinyl group.

In the above description, in the definition of R ¹ , “C 1-3 which may be substituted by 1 to 3 groups selected from substituent group β”
The C ₇ -C ₁₁ arylcarbonylamino portion of the “ _7- C ₁₁ arylcarbonylamino group” indicates a group in which a carbonylamino group is bonded to the C ₆ -C ₁₀ aryl group, and examples thereof include phenylcarbonylamino and indenylcarbonylamino. And a naphthylcarbonylamino group, preferably a phenylcarbonylamino group. Further, the substituent group β
1 to 3 substituents (preferably one) selected from the group consisting of the substituent group β2, preferably the group β3. Is the group of choice.

The “C ₇ -C ₁₁ arylcarbonylamino group optionally substituted by 1 to 3 groups selected from the substituent group β” is, for example, phenylcarbonylamino, 2-, 3- or 4-methylphenylcarbonylamino, 2-, 3- or 4-ethylphenylcarbonylamino, 2-, 3- or 4-methoxyphenylcarbonylamino, 2-, 3- or 4-fluorophenylcarbonylamino, 2-, 3 -Or 4-chlorophenylcarbonylamino, (inden-1-yl)
Carbonylamino, (inden-2-yl) carbonylamino, (naphthalen-1-yl) carbonylamino,
A (naphthalen-2-yl) carbonylamino group,
It is preferably a phenylcarbonylamino group which may be substituted with a group selected from the substituent group β2, and particularly preferably a phenylcarbonylamino group which may be substituted with a group selected from the substituent group β3. .

In the above, the “tetrazolylcarbonylamino group which may be substituted by 1 to 3 groups selected from the substituent group β” in the definition of R ¹ is, for example, (1H-
(Tetrazol-5-yl) carbonylamino, (1-methyltetrazol-5-yl) carbonylamino, (1
-Ethyltetrazol-5-yl) carbonylamino,
(1-methoxytetrazol-5-yl) carbonylamino, (1-fluorotetrazol-5-yl) carbonylamino, and (1-chlorotetrazol-5-yl) carbonylamino group. Is a tetrazolylcarbonylamino group which may be substituted with a group selected from the substituent group β2, and particularly preferably a tetrazolyl group which may be substituted with a group selected from the substituent group β3. It is a carbonylamino group.

In the above, in the definition of R ¹ , “(C ₆ -C ₁₀ aryl) sulfonylcarbamoylamino group which may be substituted by 1 to 3 groups selected from substituent group β” The C ₆ -C ₁₀ aryl) sulfonylcarbamoylamino moiety represents a group in which an amino group is bonded to the (C ₆ -C ₁₀ aryl) sulfonylcarbamoyl group, for example, phenylsulfonylcarbamoylamino, indenylsulfonylcarbamoylamino, naphthylsulfonyl A carbamoylamino group, preferably a phenylsulfonylcarbamoylamino group. In addition, 1 to 3 substituents (preferably 1) selected from the substituent group β are preferably groups selected from the substituent group β1, and more preferably the substituents A group selected from group β2, more preferably C ₁ -C ₂ alkyl, methoxy,
It is a fluorine atom or a chlorine atom, particularly preferably a methyl group.

One to three of such a group selected from the substituent group β may be substituted (C ₆ -C ₁₀ aryl)
"Sulfonylcarbamoylamino group" includes, for example, phenylsulfonylcarbamoylamino, 2-, 3- or 4-methylphenylsulfonylcarbamoylamino,
-, 3- or 4-ethylphenylsulfonylcarbamoylamino, 2-, 3- or 4-methoxyphenylsulfonylcarbamoylamino, 2-, 3- or 4-ethoxyphenylsulfonylcarbamoylamino,
2-, 3- or 4-fluorophenylsulfonylcarbamoylamino, 2-, 3- or 4-chlorophenylsulfonylcarbamoylamino, indenylsulfonylcarbamoylamino, naphthylsulfonylcarbamoylamino, preferably from the substituent group β1 A phenylsulfonylcarbamoylamino group which may be substituted with a selected group, more preferably the substituent group β
A phenylsulfonylcarbamoylamino group which may be substituted with a group selected from 2 and more preferably C _1-
C ₂ alkyl, methoxy, fluorine atom or phenylsulphonyl optionally substituted by a chlorine atom carbamoylmethyl group, still more preferably a optionally substituted phenyl sulfonylcarbamoyl amino group with a methyl group,
Particularly preferred is a tosylcarbamoylamino group.

In the above, “C ₁ -C ₆ alkyl group” in the definition of R ² , R ³ , R ⁴ and the substituent group γ has the same meaning as the above C ₁ -C ₆ alkyl group. , R ² , R ³ and R ⁴ are preferably C ₁ -C ₂ alkyl groups, particularly preferably methyl groups, and in the substituent group γ, preferably C ₁ -C ₂ alkyl groups Or a t-butyl group, more preferably a methyl group or a t-butyl group, particularly preferably a methyl group.

In the above, “C ₁ -C ₆ alkoxy group” in the definition of R ² , R ³ , R ⁴ and the substituent group γ is:
It has the same meaning as the C ₁ -C ₆ alkoxy group, and is preferably a C ₁ -C ₂ alkoxy group, and particularly preferably a methoxy group.

[0041] At a above, R ^2, R ^3, R ⁴ and in the definition of Substituent group γ "halogen atom", the a halogen atom as defined above, in R ² is preferably a fluorine An atom or a chlorine atom, particularly preferably a fluorine atom. R ³ and R ⁴ are preferably a fluorine atom or a chlorine atom.

In the above, "mono- (C ₁ -C ₆ alkyl) amino group" in the definition of R ² , R ³ and R ⁴
Has the same meaning as the above mono- (C ₁ -C ₆ alkyl) amino group, and is preferably a mono- (C ₁ -C ₂ alkyl) amino group.

In the above, the “di- (C ₁ -C ₆ alkyl) amino group” in the definition of R ² , R ³ and R ⁴ is
It has the same meaning as the above-mentioned di- (C ₁ -C ₆ alkyl) amino group, and is preferably a di- (C ₁ -C ₂ alkyl) amino group.

In the above description, in the definition of R ⁵ , “C 1-3 which may be substituted by 1 to 3 groups selected from substituent group β”
The C ₆ -C ₁₀ aryl part of the “ _6- C ₁₀ aryl group” has the same meaning as the above C ₆ -C ₁₀ aryl group, and is preferably a phenyl or naphthyl group, and particularly preferably a phenyl group. In addition, 1 to 3 substituents (preferably 1) selected from the substituent group β are preferably groups selected from the substituent group β1, and more preferably It is a group selected from the substituent group β2, more preferably a group selected from the substituent group β3, and particularly preferably a methoxy group. Such “C ₆ -C ₁₀ aryl group optionally substituted by 1 to 3 groups selected from substituent group β” is, for example, phenyl, 2-, 3- or 4-methylphenyl, 2-methylphenyl, , 3- or 4-ethylphenyl, 2-, 3- or 4-methoxyphenyl, 2-,
3- or 4-chlorophenyl, 2-, 3- or 4-fluorophenyl, 4-methyl-2-methoxyphenyl, 6-fluoro-4-methyl-2-methoxyphenyl, 2,3-dimethoxyphenyl, 2,4 -Dimethoxyphenyl, 3,4-dimethoxyphenyl, 3,5-dimethoxyphenyl, 2,3,4-trimethoxyphenyl,
3,4,5-trimethoxyphenyl, inden-2- or 3-yl, 5-methylinden-2-yl, 5-
A methylinden-3-yl, naphthalen-1- or 2-yl, 5-methylnaphthalen-1-yl or 5-methylnaphthalen-2-yl group, preferably a group selected from the substituent group β1 And more preferably a phenyl or naphthyl group, more preferably the substituent group β2
And more preferably a phenyl group optionally substituted with a group selected from the substituent group β3, and even more preferably phenyl, 2-phenyl , 3- or 4-methoxyphenyl,
2,3-dimethoxyphenyl, 2,4-dimethoxyphenyl, 3,4-dimethoxyphenyl, 3,5-dimethoxyphenyl or 3,4,5-trimethoxyphenyl, even more preferably phenyl or 2-,
It is a 3- or 4-methoxyphenyl group, particularly preferably a phenyl group.

In the above, in the definition of R ⁵ , “1 to 3 groups may be substituted with a group selected from the substituent group β,
Thienyl, pyrrolyl, which may be condensed with a benzene ring,
One to three substituents (preferably one) selected from the substituent group β of the “1,1-dioxythienyl, thiazolyl or oxazolyl group” are preferably selected from the substituent group β1. And more preferably a group selected from the substituent group β2, and particularly preferably a group selected from the substituent group β3.

Such a "thienyl, pyrrolyl or 1,1-dioxythienyl group which may be substituted by 1 to 3 groups selected from the substituent group β and may be condensed with a benzene ring" includes, for example, , Thiophen-2-yl, 3-,
4- or 5-methylthiophen-2-yl, 3-,
4- or 5-ethylthiophen-2-yl, 3-,
4- or 5-methoxythiophen-2-yl, 3
-, 4- or 5-fluorothiophen-2-yl,
3-, 4- or 5-chlorothiophen-2-yl,
Thiophen-3-yl, 2-, 4- or 5-methylthiophen-3-yl, 2-, 4- or 5-ethylthiophen-3-yl, 2-, 4- or 5-methoxythiophen-3-yl , 2-, 4- or 5-fluorothiophen-3-yl, 2-, 4- or 5-chlorothiophen-3-yl, pyrrol-1-yl, pyrrol-2-yl, 1-, 3-, 4 -Or 5-methylpyrrol-2-yl, 1-, 3-, 4- or 5-ethylpyrrol-2-yl, 1-, 3-, 4- or 5
-Methoxypyrrole-2-yl, 1-, 3-, 4- or 5-fluoropyrrol-2-yl, 1-, 3-, 4
-Or 5-chloropyrrol-2-yl, pyrrole-
3-yl, 1-, 2-, 4- or 5-methylpyrrol-3-yl, 1-, 2-, 4- or 5-ethylpyrrol-3-yl, 1-, 2-, 4- or 5 -Methoxypyrrole-3-yl, 1-, 2-, 4- or 5
-Fluoropyrrol-3-yl, 1-, 2-, 4- or 5-chloropyrrol-3-yl, 1,1-dioxothiophen-2-yl, 3-, 4- or 5-methyl-1, 1-dioxothiophen-2-yl, 1,1-dioxothiophen-3-yl, 2-, 4- or 5-
Methyl-1,1-dioxothiophen-3-yl, thiazol-5-yl, 2- or 4-methylthiazol-5-yl, oxazol-5-yl, 2- or 4
-Methyloxazol-5-yl, benzothiophene-
2-yl, 3-, 4- or 5-methylbenzothiophen-2-yl, 3-, 4- or 5-methoxybenzothiophen-2-yl, 3-, 4- or 5-fluorobenzothiophen-2- Yl, 3-, 4- or 5-chlorobenzothiophen-2-yl, benzothiophen-3-yl, 2-, 4- or 5-methylbenzothiophen-3-yl, 2-, 4- or 5-methoxy Benzothiophen-3-yl, 2-, 4- or 5
-Fluorobenzothiophen-3-yl, 2-, 4- or 5-chlorobenzothiophen-3-yl, indol-1-yl, indol-2-yl, 1-, 3-,
4- or 5-methylindol-2-yl, 3-,
4- or 5-methoxyindol-2-yl, 3
-, 4- or 5-fluoroindol-2-yl,
3-, 4- or 5-chloroindol-2-yl,
Indole-3-yl, 1-, 2-, 4- or 5-
Methylindol-3-yl, 2-, 4- or 5-
Methoxyindol-3-yl, 2-, 4- or 5
-Fluoroindol-3-yl, 2-, 4- or 5-chloroindol-3-yl, 1,1-dioxobenzothiophen-2-yl, 3-, 4-, 5-, 6- or 7- Methyl-1,1-dioxobenzothiophen-2-yl, 3-, 4-, 5-, 6- or 7-methoxy-1,1-dioxobenzothiophen-2-yl,
3-, 4-, 5-, 6- or 7-fluoro-1,1
-Dioxobenzothiophen-2-yl, 3-, 4-,
5-, 6- or 7-chloro-1,1-dioxobenzothiophen-2-yl, 1,1-dioxobenzothiophen-3-yl, 2-, 4-, 5-, 6- or 7
-Methyl-1,1-dioxobenzothiophen-3-yl, 2-, 4-, 5-, 6- or 7-methoxy-
1,1-dioxobenzothiophen-3-yl, 2-,
4-, 5-, 6- or 7-fluoro-1,1-dioxobenzothiophen-3-yl, 2-, 4-, 5-,
6- or 7-chloro-1,1-dioxobenzothiophen-3-yl, benzothiazol-2-yl, 4
-, 5-, 6- or 7-methylbenzothiazole-
2-yl, benzoxazol-2-yl, 4-, 5
-, 6- or 7-methylbenzoxazole-2-
Thienyl, 1,1-dioxothienyl, thiazolyl, benzothienyl, 1,1-dioxobenzothienyl or benzothiazolyl, which is an yl group, which may be preferably substituted with a group selected from the substituent group β1. Group,
More preferably, it is a thienyl, thiazolyl, benzothienyl or 1,1-dioxobenzothienyl group which may be substituted with a group selected from the substituent group β2, more preferably from the substituent group β3. It is a benzothienyl group or a 1,1-dioxobenzothienyl group which may be substituted with a selected group, particularly preferably 1,1-dioxobenzothiophen-3-yl.

[0047] The above At a, in the definition of R ⁶ 'C ₁ -
The “C ₁₀ alkyl group” is a straight-chain or branched-chain hydrocarbon group having 1 to 10 carbon atoms, for example, the aforementioned C ₁ -C ₆ alkyl, heptyl, 1-methylhexyl, 2-methylhexyl, Methylhexyl, 4-methylhexyl, 5
-Methylhexyl, 1-propylbutyl, 1-ethylpentyl, 2-ethylpentyl, 3-ethylpentyl,
-Ethylpentyl, 4,4-dimethylpentyl, octyl, 1-methylheptyl, 2-methylheptyl, 3-methylheptyl, 4-methylheptyl, 5-methylheptyl, 6-methylheptyl, 1-propylpentyl, 2-
Propylpentyl, 3-propylpentyl, 4-propylpentyl, 1-ethylhexyl, 2-ethylhexyl, 3-ethylhexyl, 4-ethylhexyl, 5-ethylhexyl, 5,5-dimethylhexyl, nonyl,
-Methyloctyl, 4-methyloctyl, 5-methyloctyl, 6-methyloctyl, 1-propylhexyl,
2-propylhexyl, 3-propylhexyl, 4-propylhexyl, 5-propylhexyl, 2-ethylheptyl, 6,6-dimethylheptyl, 1-butylpentyl, 2-butylpentyl, 3-butylpentyl, 4-butyl Pentyl, 1-butylhexyl, 2-butylhexyl, 3-butylhexyl, 4-butylhexyl, 5-butylhexyl, decyl, 1-methylnonyl, 3-methylnonyl, 8-methylnonyl, 3-ethyloctyl, 3,
7-dimethyl-octyl, a 7,7-dimethyl octyl group, preferably a C ₃ -C ₈ alkyl group, more preferably, isopropyl, butyl, t- butyl, neopentyl, 1-ethylpentyl or 2 An ethylhexyl group, particularly preferably a 1-ethylpentyl group.

In the above description, “C ₁ -C ₆ alkylene group” in the definition of W and Z includes, for example, methylene, methylmethylene, ethylene, propylene, trimethylene,
1-methylethylene, tetramethylene, 1-methyltrimethylene, 2-methyltrimethylene, 3-methyltrimethylene, 1-methylpropylene, 1,1-dimethylethylene, pentamethylene, 1-methyltetramethylene,
-Methyltetramethylene, 3-methyltetramethylene,
4-methyltetramethylene, 1,1-dimethyltrimethylene, 2,2-dimethyltrimethylene, 3,3-dimethyltrimethylene, hexamethylene, 1-methylpentamethylene, 2-methylpentamethylene, 3-methylpentamethylene , 4-methylpentamethylene, 5-methylpentamethylene, 1,1-dimethyltetramethylene, 2,2
-Dimethyltetramethylene, 3,3-dimethyltetramethylene, and 4,4-dimethyltetramethylene groups, preferably C ₁ -C ₂ alkylene groups, and particularly preferably methylene groups.

In the definition of R ⁷ , “C ₃ -C ₆ cycloalkyl which may be substituted with 1 to 3 groups selected from the substituent group γ and may be condensed with a benzene ring” The C ₃ -C ₆ cycloalkyl moiety of the group “C ₃ -C ₆
It has the same meaning as a cycloalkyl group, and may be condensed with a benzene ring. Such a C ₃ -C ₆ cycloalkyl group, for example, the C ₃ -C ₆ cycloalkyl, indanyl, a benzo cyclohexyl group, preferably, may be condensed with the benzene ring C ₅ -C ₆ It is a cycloalkyl group, particularly preferably a cyclohexyl group.

Further, 1 to 3 selected from the substituent group γ
Substituents (preferably one) are the aforementioned C ₁ -C
₆ alkyl group, the C ₁ -C ₆ alkoxy group, the halogen atom and the formula —ZR ⁸ , wherein Z is a single bond or the C ₁ -C ₆ alkylene group, and R ⁸ is a carboxy group , C ₂ -C ₇ alkoxycarbonyl group (wherein the C ₁
-C _{6 represents a} group in which a carbonyl group is bonded to an alkoxy group, for example, methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, butoxycarbonyl, isobutoxycarbonyl, s
-Butoxycarbonyl, t-butoxycarbonyl, pentoxycarbonyl, isopentoxycarbonyl, 2-methylbutoxycarbonyl, neopentoxycarbonyl,
1-ethylpropoxycarbonyl, hexyloxycarbonyl, 4-methylpentoxycarbonyl, 3-methylpentoxycarbonyl, 2-methylpentoxycarbonyl, 1-methylpentoxycarbonyl, 3,3-dimethylbutoxycarbonyl, 2,2- Dimethylbutoxycarbonyl, 1,1-dimethylbutoxycarbonyl, 1,2
-Dimethylbutoxycarbonyl, 1,3-dimethylbutoxycarbonyl, 2,3-dimethylbutoxycarbonyl, 2-ethylbutoxycarbonyl, preferably C ₂ -C ₃ alkoxycarbonyl, particularly preferably methoxycarbonyl Group. ), Carbamoyl group,
Mono- (C ₁ -C ₆ alkyl) carbamoyl group (indicating a group in which _one C ₁ -C ₆ alkyl group is bonded to a carbamoyl group, for example, methylcarbamoyl, ethylcarbamoyl, propylcarbamoyl, isopropylcarbamoyl, butylcarbamoyl , Isobutylcarbamoyl,
s-butylcarbamoyl, t-butylcarbamoyl, pentylcarbamoyl, isopentylcarbamoyl, 2-
Methylbutylcarbamoyl, neopentylcarbamoyl, 1-ethylpropylcarbamoyl, and hexylcarbamoyl, preferably C ₁ -C ₂ alkylcarbamoyl. ), A di- (C ₁ -C ₆ alkyl) carbamoyl group [showing a group in which two same or different C ₁ -C ₆ alkyl groups are bonded to a carbamoyl group;
Dimethylcarbamoyl, diethylcarbamoyl, N-ethyl-N-methylcarbamoyl, dipropylcarbamoyl, diisopropylcarbamoyl, N-methyl-N-propylcarbamoyl, dibutylcarbamoyl, diisobutylcarbamoyl, di-s-butylcarbamoyl, di-
t-butylcarbamoyl, N-butyl-N-methylcarbamoyl, dipentylcarbamoyl, N-ethyl-N-
Propylcarbamoyl, N-butyl-N-ethylcarbamoyl, dihexylcarbamoyl, N-butyl-N-propylcarbamoyl, preferably di- (C ₁ -C
₂ alkyl) carbamoyl group, particularly preferably a dimethylcarbamoyl group. And the aforementioned C ₁ -C ₆ alkylsulfonyl group or hydroxyl group. And a group having｝. Preferably, a C ₁ -C ₂ alkyl group, a t-butyl group, a C ₁ -C ₂ alkoxy group, a fluorine atom, a chlorine atom and a formula —ZR ^{8 wherein} Z is a single bond or C _1- C ₂
An alkylene group, R ⁸ is a carboxy group, C ₂ -C
₃ alkoxycarbonyl group, carbamoyl group, mono-
(C ₁ -C ₂ alkyl) carbamoyl group, di- (C _1-
(C ₂ alkyl) carbamoyl, C ₁ -C ₄ alkylsulfonyl or hydroxyl. A group selected from the group consisting of the following groups (hereinafter referred to as a substituent group γ1), more preferably a methyl group, a t-butyl group,
A substituent group consisting of a methoxy group, a fluorine atom, a chlorine atom, a carboxy group, a methoxycarbonyl group, a dimethylcarbamoyl group and a hydroxymethyl group (hereinafter referred to as a substituent group γ2
That. ), And particularly preferably a group selected from a substituent group consisting of a methyl group, a methoxy group, a fluorine atom and a chlorine atom (hereinafter referred to as a substituent group γ3).

The “C ₃ -C ₆ cycloalkyl group which may be substituted by 1 to 3 groups selected from the substituent group γ and may be condensed with a benzene ring” is, for example, cyclopentyl, cyclohexyl , 2-, 3- or 4-methylcyclohexyl, 2-, 3- or 4-ethylcyclohexyl, 2-, 3- or 4-t-butylcyclohexyl, 2-, 3- or 4-methoxycyclohexyl, 2-, 3- or 4-fluorocyclohexyl, 2-, 3- or 4-chlorocyclohexyl, 2
-, 3- or 4-carboxycyclohexyl, 2
-, 3- or 4-methoxycarbonyl-cyclohexyl, 2-, 3- or 4-carbamoylcyclohexyl, 2-, 3- or 4-methylcarbamoylcyclohexyl, 2-, 3- or 4-dimethylcarbamoylcyclohexyl, 2-, 3- or 4-methylsulfonylcyclohexyl, 2-, 3- or 4-hydroxycyclohexyl, 2-, 3- or 4-hydroxymethylcyclohexyl, indan-1-yl, indan-2-yl group, preferably wherein a substituent group γ1 is substituted by a group selected from optionally combined well benzene ring condensed be C ₅ -C ₆ cycloalkyl group, more preferably a group selected from the substituent group γ2 be substituted is a well-fused to a benzene ring optionally C ₅ -C be ₆ cycloalkyl group, and more The suitable a good cyclohexyl group optionally substituted with a group selected from the substituent group [gamma] 3,
Particularly preferred is a cyclohexyl group.

In the above description, in the definition of R ⁶ , “C 1-3 which may be substituted by 1 to 3 groups selected from the substituent group γ”
The C ₇ -C ₁₆ aralkyl portion of the “ _7- C ₁₆ aralkyl group” indicates a group in which the C ₁ -C ₆ alkyl group is bonded to the C ₆ -C ₁₀ aryl group, and examples thereof include benzyl, naphthylmethyl, and indenyl. Methyl, 1-phenylethyl, 2-
Phenylethyl, 1-naphthylethyl, 2-naphthylethyl, 1-phenylpropyl, 2-phenylpropyl,
3-phenylpropyl, 1-naphthylpropyl, 2-naphthylpropyl, 3-naphthylpropyl, 1-phenylbutyl, 2-phenylbutyl, 3-phenylbutyl,
-Phenylbutyl, 1-naphthylbutyl, 2-naphthylbutyl, 3-naphthylbutyl, 4-naphthylbutyl,
-Phenylpentyl, 2-phenylpentyl, 3-phenylpentyl, 4-phenylpentyl, 5-phenylpentyl, 1-naphthylpentyl, 2-naphthylpentyl, 3-naphthylpentyl, 4-naphthylpentyl, 5
-Naphthylpentyl, 1-phenylhexyl, 2-phenylhexyl, 3-phenylhexyl, 4-phenylhexyl, 5-phenylhexyl, 6-phenylhexyl, 1-naphthylhexyl, 2-naphthylhexyl, 3
-Naphthylhexyl, 4-naphthylhexyl, 5-naphthylhexyl, 6-naphthylhexyl, preferably the aryl moiety is a phenyl group and the alkyl moiety is C
An ₁ -C ₄ aralkyl group which is an alkyl group, more preferably benzyl, 1-phenylethyl or 2-phenylethyl group, particularly preferably a 1-phenylethyl group.

Further, 1 to 3 selected from the substituent group γ
Substituents (preferably one) have the same meaning as the substituent group γ, and are preferably selected from the substituent group γ1, and more preferably the substituent group γ1. A group selected from the group γ2, and particularly preferably a group selected from the substituent group γ3.

Such a “C ₇ -C ₁₆ aralkyl group optionally substituted by 1 to 3 groups selected from the substituent group γ” is, for example, benzyl, 2-, 3- or 4-methylbenzyl , 2-, 3- or 4-ethylbenzyl, 2-, 3- or 4-methoxybenzyl, 2-,
3- or 4-fluorobenzyl, 2-, 3- or 4-chlorobenzyl, 2-, 3- or 4-carboxybenzyl, 2-, 3- or 4-carbamoylbenzyl, 2-, 3- or 4-dimethyl Carbamoylbenzyl, 2-, 3- or 4-hydroxybenzyl, 2-, 3- or 4-hydroxymethylbenzyl, 1- or 2-phenylethyl, 1- or 2
-(2-, 3- or 4-methylphenyl) ethyl,
1- or 2- (2-, 3- or 4-ethylphenyl) ethyl, 1- or 2- (2-, 3- or 4-methoxyphenyl) ethyl, 1- or 2- (2
-, 3- or 4-fluorophenyl) ethyl, 1-
Or 2- (2-, 3- or 4-chlorophenyl) ethyl, 1- or 2- (2-, 3- or 4
-Chlorophenyl) ethyl, 1- or 2- (2-,
3- or 4-bromophenyl) ethyl, 1- or 2- (2-, 3- or 4-carboxyphenyl)
Ethyl, 1- or 2- (2-, 3- or 4-carbamoylphenyl) ethyl, 1- or 2- (2
-, 3- or 4-dimethylcarbamoylphenyl)
Ethyl, 1- or 2- (2-, 3- or 4-hydroxyphenyl) ethyl, 1- or 2- (2-, 2-
3- or 4-hydroxymethylphenyl) ethyl,
1- or 2- (naphthalen-1-yl) ethyl, 1
Or a 2- (naphthalen-2-yl) ethyl group, preferably substituted with a group selected from the above-mentioned substituent group γ1, wherein the aryl part is a phenyl group and the alkyl part is a C ₁ -C ₄ is an aralkyl group which is an alkyl group, and more preferably may be substituted with a group selected from the substituent group γ2, wherein the aryl part is a phenyl group and the alkyl part is a C ₁ -C ₄ alkyl group. An aralkyl group, more preferably a benzyl, 1-phenylethyl or 2-phenylethyl group which may be substituted with a group selected from the substituent group γ3, and particularly preferably 1
-Phenylethyl.

Among the compounds (I) of the present invention, a compound having a basic group such as an amino group can be converted into a pharmacologically acceptable salt by treating it with an acid according to a conventional method, if necessary. . Such salts include hydrofluorides,
Hydrohalides such as hydrochloride, hydrobromide and hydroiodide; inorganic salts such as nitrate, perchlorate, sulfate and phosphate; methanesulfonate and trifluoromethanesulfonic acid Salts, C ₁ -C ₆ alkane sulfonates which may be substituted by fluorine such as ethane sulfonate; C _6- such as benzene sulfonate and p-toluene sulfonate.
Sulfonates such as C ₁₀ aryl sulfonate; fumarate - le, succinate, citrate, tartrate, oxalate, carboxylates such as maleate; or glutamate, aspartic acid An amino acid salt such as a salt; preferably a hydrohalide, C
(Particularly preferred, the hydrochloride, methanesulfonate, fumarate - a le, oxalate or maleate salt.) ₁ -C ₆ alkane sulfonates or carboxylates is.

In the compound (I) of the present invention, a compound having an acidic group such as a carboxy group can be converted into a pharmacologically acceptable salt by treating it with a base according to a conventional method, if necessary. it can. Examples of such salts include alkali metal salts such as lithium salts, sodium salts and potassium salts; metal salts such as alkaline earth metal salts such as calcium salts and magnesium salts; metal salts such as aluminum salts and iron salts; Organic base salts such as ammonium salts, glucosamine salts, phenylglycine alkyl ester salts, ethylenediamine salts, N-methylglucamine salts, guanidine salts, diethylamine salts, triethylamine salts, and dicyclohexylamine salts; It is an alkali metal salt.

The compound (I) of the present invention or a pharmacologically acceptable salt thereof absorbs moisture by being left in the air or recrystallized to form adsorbed water, or to form a hydrate. In some cases, such is included in the present invention.

The compound (I) of the present invention or a pharmaceutically acceptable salt thereof may absorb some other solvent and form a solvate, and such a compound is also included in the present invention. You.

The compound (I) of the present invention or a pharmacologically acceptable salt thereof may have an asymmetric carbon atom in the molecule and may have R-configuration or S-configuration stereoisomers. However, each of the compounds, or any proportion thereof, is encompassed by the present invention. Such a stereoisomer can be obtained by using a compound (I)
Or the synthesized compound (I) can be optically resolved by a usual optical resolution or separation method, if desired.

The compound (I) of the present invention or a pharmaceutically acceptable salt thereof has a geometrical isomer when R ⁶ is a group having the formula —W—R ⁷ , Such geometric isomers are included, and preferably, the trans isomer can be mentioned.

The present invention also includes all so-called prodrugs which are metabolized in vivo and converted into benzylamines having the general formula (I) of the present invention or pharmacologically acceptable salts thereof.

Further, among the compounds having the general formula (I) contained as an active ingredient of the ileal bile acid transporter inhibitor of the present invention, the following compounds can be preferably mentioned.

(1) R ¹ is a phenyl group substituted with a group selected from substituent group α1, a tetrazolyl group optionally substituted with a group selected from substituent group β1, (C ₅ -C
₆ cycloalkyl) carbamoyl group, (C ₁ -C ₄ alkyl) sulfonylcarbamoyl group, phenylsulfonylcarbamoyl group, sulfo group, and C ₁ -C ₆ alkylsulfonyl group which may be substituted with a group selected from substituent group δ1 A phenylsulfonyl group, a methylaminosulfonyl group, an ethylaminosulfonyl group, a dimethylaminosulfonyl group, a diethylaminosulfonyl group, a C ₁ -C ₄ alkylsulfinyl group, a substituent which may be substituted with a group selected from the substituent group β1 A compound which is a phenylcarbonylamino or tetrazolylcarbonylamino group which may be substituted with a group selected from group β2, or a phenylsulfonylcarbamoylamino group which may be substituted with a group selected from substituent group β1. <Substituent group α1> Tetrazolyl group, sulfo group, C ₁ -C ₄ alkylsulfonyl group, methylsulfonylamino group, ethylsulfonylamino group and substituent group β2 which may be substituted with a group selected from substituent group β2 Phenylsulfonylamino group which may be substituted with a group selected from <substituent group β1> C ₁ -C ₄ alkyl group, C ₁ -C ₄ alkoxy group, fluorine atom and chlorine atom <substituent group β2> C ₁ —C ₂ alkyl group, C ₁ -C ₂ alkoxy group, fluorine atom and chlorine atom <Substituent group δ1> selected from C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, halogen atom and substituent group β 1 A phenyl group which may be substituted with a group;

(2) R ¹ is 2-, 3- or 4-
(1H-tetrazol-5-yl) phenyl group, 2-,
3- or 4- (1-methyltetrazol-5-yl) phenyl group, 2-, 3- or 4- (1-methoxytetrazol-5-yl) phenyl group, 2-, 3- or 4- (1- Fluorotetrazol-5-yl) phenyl group, 2-, 3- or 4- (1-chlorotetrazol-5-yl) phenyl group, 2-, 3- or 4
-Methylsulfonylphenyl group, 2-, 3- or 4
-Ethylsulfonylphenyl group, 2-, 3- or 4
-Propylsulfonylphenyl group, 2-, 3- or 4-butylsulfonylphenyl group, 2-, 3- or 4-methylsulfonylaminophenyl group, 2-, 3- or 4-phenylsulfonylaminophenyl group, substituent groups a tetrazolyl group which may be substituted with a group selected from β2, a (C ₁ -C ₂ alkyl) sulfonylcarbamoyl group, a phenylsulfonylcarbamoyl group which may be substituted with a group selected from substituent group δ2, C _1- A C ₄ alkylsulfonyl group, a phenylsulfonyl group which may be substituted with a group selected from the substituent group β2, a C ₁ -C ₂ alkylsulfinyl group, a group selected from the substituent group β3, Substituted with a phenylcarbonylamino or tetrazolylcarbonylamino group or a group selected from substituent group β2 A phenylsulfonylcarbamoylamino group which may be substituted. <Substituent group β2> C ₁ -C ₂ alkyl group, C ₁ -C ₂ alkoxy group, fluorine atom and chlorine atom <Substituent group β3> Methyl group, methoxy group, fluorine atom and chlorine atom <Substituent group δ2> A C ₁ -C ₂ alkyl group, a C ₁ -C ₂ alkoxy group, a fluorine atom, a chlorine atom and a phenyl group which may be substituted with a group selected from the substituent group β2.

(3) R ¹ is 2-, 3- or 4-
(1H-tetrazol-5-yl) phenyl group, 2-,
3- or 4-methylsulfonylphenyl group, 2-,
3- or 4-ethylsulfonylphenyl group, tetrazolyl group optionally substituted with a group selected from substituent group β2, phenylsulfonylcarbamoyl group optionally substituted with a group selected from substituent group δ3, methylsulfonyl Group, ethylsulfonyl group, propylsulfonyl group, butylsulfonyl group, phenylsulfonyl group which may be substituted with a group selected from the group of substituents β3, or phenylsulfonylcarbamoylamino group which may be substituted (the substituent is ₁ -C ₂ alkyl, methoxy, fluorine or chlorine), compound. <Substituent group β2> C ₁ -C ₂ alkyl group, C ₁ -C ₂ alkoxy group, fluorine atom and chlorine atom <Substituent group β3> Methyl group, methoxy group, fluorine atom and chlorine atom <Substituent group δ3> A methyl group, a methoxy group, a fluorine atom, a chlorine atom and a phenyl group which may be substituted by C ₁ -C ₂ alkyl, methoxy, fluorine or chlorine.

(4) R ¹ is a 2-methylsulfonylphenyl group, a 3-methylsulfonylphenyl group, a 4-methylsulfonylphenyl group, a tetrazolyl group which may be substituted with a group selected from the substituent group β3, A compound which is a phenylsulfonylcarbamoyl group optionally substituted with a group selected from group δ4, a methylsulfonyl group, an ethylsulfonyl group, a butylsulfonyl group, a phenylsulfonyl group or a phenylsulfonylcarbamoylamino group optionally substituted with methyl . <Substituent group β3> Methyl group, methoxy group, fluorine atom and chlorine atom <Substituent group δ4> Methyl group, phenyl group and methylphenyl group.

(5) When R ¹ is 1H-tetrazole-5
Compounds which are an yl group, a methylsulfonyl group, an ethylsulfonyl group or a tosylcarbamoylamino group. (6) The compound wherein R ¹ is a 1H-tetrazol-5-yl group.

(7) When R ² , R ³ and R ⁴ are the same or different and each is hydrogen atom, C ₁ -C ₂ alkyl group, C _1-
Compounds which are a C ₂ alkoxy group, a hydroxyl group, a fluorine atom, a chlorine atom, an amino group, a mono- (C ₁ -C ₂ alkyl) amino group or a di- (C ₁ -C ₂ alkyl) amino group. (8) R ² , R ³ and R ⁴ are the same or different,
Compounds which are a hydrogen atom, a methyl group, a methoxy group, a hydroxyl group, a fluorine atom or a chlorine atom. (9) The compound wherein R ² is a hydrogen atom, a methoxy group or a fluorine atom, and R ³ and R ⁴ are hydrogen atoms. (10) The compound wherein R ² , R ³ and R ⁴ are hydrogen atoms.

(11) R ⁵ may be substituted with a group selected from substituent group β1, phenyl, naphthyl, thienyl, 1,1-dioxothienyl, thiazolyl, benzothienyl, 1,1-diphenyl A compound which is an oxobenzothienyl or benzothiazolyl group. <Substituent group β1> C ₁ -C ₄ alkyl group, C ₁ -C ₄ alkoxy group, fluorine atom and chlorine atom. (12) R ⁵
Is a phenyl, thienyl, thiazolyl, benzothienyl or 1,1-dioxobenzothienyl group which may be substituted with a group selected from the substituent group β2. <Substituent group β2> a C ₁ -C ₂ alkyl group, a C ₁ -C ₂ alkoxy group, a fluorine atom and a chlorine atom (13) R ⁵
A compound which is a phenyl group, a benzothienyl group, or a 1,1-dioxobenzothienyl group which may be substituted with a group selected from the substituent group β3. <Substituent group β3> Methyl group, methoxy group, fluorine atom and chlorine atom.

(14) R ⁵ is phenyl, 2-, 3- or 4-methoxyphenyl, 2,3-dimethoxyphenyl, 2,4-dimethoxyphenyl, 3,4-dimethoxyphenyl, 3,5-dimethoxyphenyl Or three
A compound which is a 4,5-trimethoxyphenyl or 1,1-dioxobenzothiophen-3-yl group. (15) R ⁵ is phenyl or 2-, 3- or 4
-A compound which is a methoxyphenyl group. (16) The compound wherein R ⁵ is a phenyl group.

(17) R ⁶ is a C ₃ -C ₈ alkylene group, a formula —WR ⁷ [wherein W is a single bond or C ₁ -C
_{2 is an} alkylene group, and R ⁷ is a C ₅ -C ₆ cycloalkyl group which may be substituted with a group selected from the substituent group γ 1 and may be condensed with a benzene ring. Or an aralkyl group (the aryl part is a phenyl group and the alkyl part is a C ₁ -C ₄ alkyl group) which may be substituted with a group having the above formula or a group selected from the substituent group γ1. <Substituent group γ1> C ₁ -C ₂ alkyl group, t-butyl group, C ₁ -C ₂ alkoxy group, fluorine atom, chlorine atom and formula -ZR ^{8 wherein} Z is a single bond or C ₁ -C ₂
R ⁸ is carboxy, C ₂ -C ₃
Alkoxycarbonyl, carbamoyl, mono- (C _1-
C ₂ alkyl) carbamoyl, di - (C ₁ -C ₂ alkyl) carbamoyl group having a C ₁ -C ₄ alkylsulfonyl or a hydroxyl group.

(18) R ⁶ is a C ₃ -C ₈ alkylene group or a group having the formula —WR ⁷ [wherein W is a single bond or a methylene group, and R ⁷ is a substituent group γ2 And a C ₅ -C ₆ cycloalkyl group which may be substituted with a group selected from the following and may be condensed with a benzene ring. Or an aralkyl group which may be substituted with a group selected from the substituent group γ2 (the aryl part is a phenyl group and the alkyl part is C ₁
—C ₄ alkyl group. ). <Substituent group γ2> A methyl group, a t-butyl group, a methoxy group, a fluorine atom, a chlorine atom, a carboxy group, a methoxycarbonyl group, a dimethylcarbamoyl group and a hydroxymethyl group.

(19) R ⁶ may be substituted with an isopropyl group, a butyl group, a t-butyl group, a neopentyl group, a 1-ethylpentyl group, a 2-ethylhexyl group or a group selected from the substituent group γ3. , Cyclohexyl, benzyl, 1-phenylethyl or 2-phenylethyl group. <Substituent group γ3> Methyl group, methoxy group, fluorine atom and chlorine atom. (20) The compound wherein R ⁶ is a 1-ethylpentyl group, a cyclohexyl group, or a 1-phenylethyl group. (21) The compound wherein R ⁶ is a 1-ethylpentyl group or a 1-phenylethyl group.

Further, (1)-(6), (7)-(1
0), (11)-(16) and (17)-(21) are also suitably combined with each other, and examples thereof include the following.

(22) R ¹ is a phenyl group substituted with a group selected from the group of substituents α1, a tetrazolyl group optionally substituted with a group selected from the group of substituents β1, (C _5-
A (C ₆ cycloalkyl) carbamoyl group, a (C ₁ -C ₄ alkyl) sulfonylcarbamoyl group, a phenylsulfonylcarbamoyl group, a sulfo group, a C ₁ -C ₆ alkylsulfonyl which may be substituted with a group selected from the substituent group δ1 A phenylsulfonyl group, a methylaminosulfonyl group, which may be substituted with a group selected from a substituent group β1;
An ethylaminosulfonyl group, a dimethylaminosulfonyl group, a diethylaminosulfonyl group, a C ₁ -C ₄ alkylsulfinyl group, a phenylcarbonylamino or tetrazolylcarbonylamino group which may be substituted with a group selected from a substituent group β2; A phenylsulfonylcarbamoylamino group which may be substituted with a group selected from the substituent group β1, wherein R ² , R ³ and R ⁴ are the same or different and are a hydrogen atom, a C ₁ -C ₂ alkyl group,
A C ₁ -C ₂ alkoxy group, a hydroxyl group, a fluorine atom, a chlorine atom, an amino group, a mono- (C ₁ -C ₂ alkyl) amino group or a di- (C ₁ -C ₂ alkyl) amino group,
⁵ may be substituted with a group selected from the substituent group β1, phenyl, naphthyl, thienyl, thiazolyl, 1,
1-dioxothienyl, benzothienyl, 1,1-dioxobenzothienyl or benzothiazolyl group,
R ⁶ is a C ₃ -C ₈ alkylene group, a formula —WR ⁷ [wherein W is a single bond or a C ₁ -C ₂ alkylene group, and R ⁷ is selected from a substituent group γ1 it is a well fused to a benzene ring which may be C ₅ -C ₆ cycloalkyl group optionally substituted with a group. Or an aralkyl group which may be substituted with a group selected from the substituent group γ1 (where the aryl part is a phenyl group and the alkyl part is a C ₁ -C ₄
It is an alkyl group. ). <Substituent group α1> Tetrazolyl group, sulfo group, C ₁ -C ₄ alkylsulfonyl group, methylsulfonylamino group, ethylsulfonylamino group and substituent group β2 which may be substituted with a group selected from substituent group β2 Phenylsulfonylamino group which may be substituted with a group selected from <substituent group β1> C ₁ -C ₄ alkyl group, C ₁ -C ₄ alkoxy group, fluorine atom and chlorine atom <substituent group β2> C ₁ —C ₂ alkyl group, C ₁ -C ₂ alkoxy group, fluorine atom and chlorine atom <Substituent group δ1> selected from C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, halogen atom and substituent group β 1 A phenyl group which may be substituted with a group <substituent group γ1> a C ₁ -C ₂ alkyl group, a t-butyl group, a C ₁ -C ₂ alkoxy group, a fluorine atom, a chlorine atom and a formula -ZR ⁸ [formula Inside, Z is Bond or C ₁ -C ₂
R ⁸ is carboxy, C ₂ -C ₃
Alkoxycarbonyl, carbamoyl, mono- (C _1-
C ₂ alkyl) carbamoyl, di - (C ₁ -C ₂ alkyl) carbamoyl group having a C ₁ -C ₄ alkylsulfonyl or a hydroxyl group.

(23) R ¹ is 2-, 3- or 4-
(1H-tetrazol-5-yl) phenyl group, 2-,
3- or 4- (1-methyltetrazol-5-yl) phenyl group, 2-, 3- or 4- (1-methoxytetrazol-5-yl) phenyl group, 2-, 3- or 4- (1- Fluorotetrazol-5-yl) phenyl group, 2-, 3- or 4- (1-chlorotetrazol-5-yl) phenyl group, 2-, 3- or 4
-Methylsulfonylphenyl group, 2-, 3- or 4
-Ethylsulfonylphenyl group, 2-, 3- or 4
-Propylsulfonylphenyl group, 2-, 3- or 4-butylsulfonylphenyl group, 2-, 3- or 4-methylsulfonylaminophenyl group, 2-, 3- or 4-phenylsulfonylaminophenyl group, substituent groups a tetrazolyl group which may be substituted with a group selected from β2, a (C ₁ -C ₂ alkyl) sulfonylcarbamoyl group, a phenylsulfonylcarbamoyl group which may be substituted with a group selected from substituent group δ2, C _1- A C ₄ alkylsulfonyl group, a phenylsulfonyl group which may be substituted with a group selected from the substituent group β2, a C ₁ -C ₂ alkylsulfinyl group, a group selected from the substituent group β3, Substituted with a phenylcarbonylamino or tetrazolylcarbonylamino group or a group selected from substituent group β2 A phenylsulfonylcarbamoylamino group which may be selected from R ² , R ³ and R ⁴
But the same or different, a hydrogen atom, a methyl group, a methoxy group, a hydroxyl group, a fluorine atom or a chlorine atom, R ⁵
Is a phenyl, thienyl, thiazolyl, benzothienyl or 1,1-dioxobenzothienyl group optionally substituted with a group selected from substituent group β2, and R ⁶
Is a C ₃ -C ₈ alkylene group, a group having the formula —WR ⁷ [wherein W is a single bond or a methylene group, and R ⁷
It is may be substituted with a group selected from substituent group γ2 fused to a benzene ring which may be C ₅ -C ₆ cycloalkyl group. Or a aralkyl group (the aryl part is a phenyl group and the alkyl part is a C ₁ -C ₄ alkyl group) which may be substituted with a group selected from the substituent group γ2. <Substituent group β2> C ₁ -C ₂ alkyl group, C ₁ -C ₂ alkoxy group, fluorine atom and chlorine atom <Substituent group β3> Methyl group, methoxy group, fluorine atom and chlorine atom <Substituent group δ2> A phenyl group which may be substituted with a C ₁ -C ₂ alkyl group, a C ₁ -C ₂ alkoxy group, a fluorine atom, a chlorine atom and a group selected from a substituent group β 2 <substituent group γ 2> methyl group, t- Butyl, methoxy, fluorine, chlorine, carboxy, methoxycarbonyl, dimethylcarbamoyl and hydroxymethyl groups.

(24) When R ¹ is 2-, 3- or 4-
(1H-tetrazol-5-yl) phenyl group, 2-,
3- or 4-methylsulfonylphenyl group, 2-,
3- or 4-ethylsulfonylphenyl group, tetrazolyl group optionally substituted with a group selected from substituent group β2, phenylsulfonylcarbamoyl group optionally substituted with a group selected from substituent group δ3, methylsulfonyl Group, ethylsulfonyl group, propylsulfonyl group, butylsulfonyl group, phenylsulfonyl group which may be substituted with a group selected from the group of substituents β3, or phenylsulfonylcarbamoylamino group which may be substituted (the substituent is ₁ -C ₂ alkyl, methoxy, fluorine or chlorine), R ² is a hydrogen atom, a methoxy group or a fluorine atom, R ³ and R ⁴ is hydrogen atom, and R ^5,
A phenyl group, a benzothienyl group or a 1,1-dioxobenzothienyl group which may be substituted with a group selected from the substituent group β3, wherein R ⁶ is an isopropyl group, a butyl group, a t-butyl group, a neopentyl A cyclohexyl, benzyl, 1-phenylethyl or 2-phenylethyl group, which may be substituted with a group, a 1-ethylpentyl group, a 2-ethylhexyl group or a group selected from substituent group γ3. <Substituent group β2> C ₁ -C ₂ alkyl group, C ₁ -C ₂ alkoxy group, fluorine atom and chlorine atom <Substituent group β3> Methyl group, methoxy group, fluorine atom and chlorine atom <Substituent group δ3> Methyl group, methoxy group, fluorine atom, chlorine atom and phenyl group which may be substituted by C ₁ -C ₂ alkyl, methoxy, fluorine or chlorine <substituent group γ3> methyl group, methoxy group, fluorine atom and chlorine atom.

(25) R ¹ is a 2-methylsulfonylphenyl group, a 3-methylsulfonylphenyl group, a 4-methylsulfonylphenyl group, a tetrazolyl group which may be substituted with a group selected from the group of substituents β3, A phenylsulfonylcarbamoyl group optionally substituted with a group selected from Group δ4, a methylsulfonyl group, an ethylsulfonyl group, a butylsulfonyl group, a phenylsulfonylcarbamoylamino group optionally substituted with methyl, R ² is a hydrogen atom, a methoxy group or a fluorine atom, R ³ and R ⁴ are hydrogen atoms, and R ⁵ is phenyl, 2-, 3- or 4-methoxyphenyl, 2,3-dimethoxyphenyl, , 4-dimethoxyphenyl, 3,4-dimethoxyphenyl, 3,
5-dimethoxyphenyl or 3,4,5-trimethoxyphenyl or 1,1-dioxobenzothiophene
A compound which is a 3-yl group and R ⁶ is a 1-ethylpentyl group, a cyclohexyl group or a 1-phenylethyl group. <Substituent group β3> Methyl group, methoxy group, fluorine atom and chlorine atom <Substituent group δ4> Methyl group, phenyl group and methylphenyl group.

(26) When R ¹ is 1H-tetrazole-5
-Yl, methylsulfonyl, ethylsulfonyl or tosylcarbamoylamino, R ² , R ³ and R ⁴ are hydrogen and R ⁵ is phenyl or 2-, 3- or 4-methoxyphenyl And R is
⁶ is a compound wherein 1 is a 1-ethylpentyl group or a 1-phenylethyl group.

(27) When R ¹ is 1H-tetrazole-5
A compound wherein R ² , R ³ and R ⁴ are a hydrogen atom, R ⁵ is a phenyl group and R ⁶ is a 1-ethylpentyl group or a 1-phenylethyl group.

As the representative compounds of the present invention, for example, the compounds described in Tables 1, 2 and 3 can be exemplified, but the present invention is not limited to these compounds. The compounds in Tables 1, 2, and 3 have the structural formulas (Ia), (Ib), and (Ic), respectively.

[0082]

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[0083]

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[0084]

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However, in the above formula, R ¹ , R ² , R
³ , R ⁴ , R ⁵ and R ⁶ have the same meanings as described above, R ^5a represents a phenyl group which may be substituted by 1 to 3 groups selected from substituent group β, and R ^5b Is the substituent group β
Group 1 or may be three substituents at chosen from, indenyl or naphthyl group, R ^5c is substituent group β
Thienyl, pyrrolyl, 1,1-
Represents a dioxothienyl, thiazolyl or oxazolyl group.

The abbreviations in the table are as follows. BOxa: benzoxazolyl group BThi: benzothienyl group BThiz: benzothiazolyl group Bu: butyl group tBu: t-butyl group Bz: benzyl group Et: ethyl group Hx: hexyl group cHx: cyclohexyl group Ind: indolyl group Inda: indanyl group Inde: indenyl group Me: methyl group Np: naphthyl group Oxa: oxazolyl group Ph: phenyl group cPn: cyclopentyl group nPn: neopentyl group Pn: pentyl group Pr: propyl group iPr: isopropyl group Pyrr: pyrrolyl group Thi: thienyl group Thiz: Thiazolyl group Tol: tolyl group Tz: 1H-tetrazol-5-yl group.

[0087]

[Table 1]  R¹ R^Two R^Three R^Four R^5a R⁶  1-1 2- (2-Tz-Ph) HHH Ph 1-Et-Pn 1-2 2- (2-Tz-Ph) HHH Ph cHx 1-3 2- (2-Tz-Ph) HHH Ph -CH (Ph) Me 1-4 2- (3-Tz-Ph) HHH Ph tBu 1-5 2- (3-Tz-Ph) HHH Ph 1-Et-Pn 1-6 2- (3-Tz-Ph) HHH Ph 2-Et-Hx 1-7 2- (3-Tz-Ph) HHH Ph cHx 1-8 2- (3-Tz-Ph) HHH Ph 4-Me-cHx 1-9 2- (3-Tz -Ph) HHH Ph Bz 1-10 2- (3-Tz-Ph) HHH Ph -CH (Ph) Me 1-11 2- (3-Tz-Ph) HHH Ph -CH (4-Me-Ph) Me 1-12 2- (3-Tz-Ph) 4-Me HH Ph 1-Et-Pn 1-13 2- (4-Tz-Ph) HHH Ph 1-Et-Pn 1-14 2- (4-Tz -Ph) HHH Ph cHx 1-15 2- (4-Tz-Ph) HHH Ph -CH (Ph) Me 1-16 3- (2-Tz-Ph) HHH Ph 1-Et-Pn 1-17 3- (2-Tz-Ph) HHH Ph cHx 1-18 3- (2-Tz-Ph) HHH Ph -CH (Ph) Me 1-19 3- (3-Tz-Ph) HHH Ph tBu 1-20 3- (3-Tz-Ph) HHH Ph 1-Et-Pn 1-21 3- (3-Tz-Ph) HHH Ph 2-Et-Hx 1-22 3- (3-Tz-Ph) HHH Ph cHx 1- 23 3- (3-Tz-Ph) HHH Ph 4-Me-cHx 1-24 3- (3-Tz-Ph) HHH Ph Bz 1-25 3- (3-Tz-Ph) HHH Ph -CH (Ph ) Me 1-26 3- (3-Tz-Ph) HHH Ph -CH (4-Me-Ph) Me 1-27 3- (4-Tz-Ph) HHH Ph 1-Et-Pn 1-28 3- (4-Tz-Ph) HHH Ph cHx 1-29 3- (4-Tz-Ph) HHH Ph -CH (Ph) Me 1-30 4- (2-Tz-Ph) HHH Ph 1-Et-P n 1-31 4- (2-Tz-Ph) HHH Ph cHx 1-32 4- (2-Tz-Ph) HHH Ph -CH (Ph) Me 1-33 4- (3-Tz-Ph) HHH Ph tBu 1-34 4- (3-Tz-Ph) HHH Ph 1-Et-Pn 1-35 4- (3-Tz-Ph) HHH Ph 2-Et-Hx 1-36 4- (3-Tz-Ph ) HHH Ph cHx 1-37 4- (3-Tz-Ph) HHH Ph 4-Me-cHx 1-38 4- (3-Tz-Ph) HHH Ph Bz 1-39 4- (3-Tz-Ph) HHH Ph -CH (Ph) Me 1-40 4- (3-Tz-Ph) HHH Ph -CH (4-Me-Ph) Me 1-41 4- (4-Tz-Ph) HHH Ph 1-Et- Pn 1-42 4- (4-Tz-Ph) HHH Ph cHx 1-43 4- (4-Tz-Ph) HHH Ph -CH (Ph) Me 1-44 2- (2-Tz-Ph) HHH Ph 1-Inda 1-45 2- (2-Tz-Ph) HHH Ph -CH (4-Br-Ph) Me 1-46 2- (2-Tz-Ph) HHH Ph -CH (1-Np) Me 1 -47 2- (3-Tz-Ph) HHH Ph 1-Inda 1-48 2- (3-Tz-Ph) HHH Ph -CH (4-Br-Ph) Me 1-49 2- (3-Tz- Ph) HHH Ph -CH (1-Np) Me 1-50 2- (4-Tz-Ph) HHH Ph 1-Inda 1-51 2- (4-Tz-Ph) HHH Ph -CH (4-Br- Ph) Me 1-52 2- (4-Tz-Ph) HHH Ph -CH (1-Np) Me 1-53 3- (2-Tz-Ph) HHH Ph 1-Inda 1-54 3- (2- Tz-Ph) HHH Ph -CH (4-Br-Ph) Me 1-55 3- (2-Tz-Ph) HHH Ph -CH (1-Np) Me 1-56 3- (3-Tz-Ph) HHH Ph 1-Inda 1-57 3- (3-Tz-Ph) HHH Ph -CH (4-Br-Ph) Me 1-58 3- (3-Tz-Ph) HHH Ph -CH (1-Np) Me 1- 59 3- (4-Tz-Ph) HHH Ph 1-Inda 1-60 3- (4-Tz-Ph) HHH Ph -CH (4-Br-Ph) Me 1-61 3- (4-Tz-Ph ) HHH Ph -CH (1-Np) Me 1-62 4- (2-Tz-Ph) HHH Ph 1-Inda 1-63 4- (2-Tz-Ph) HHH Ph -CH (4-Br-Ph) ) Me 1-64 4- (2-Tz-Ph) HHH Ph -CH (1-Np) Me 1-65 4- (3-Tz-Ph) HHH Ph 1-Inda 1-66 4- (3-Tz -Ph) HHH Ph -CH (cHx) Me 1-67 4- (3-Tz-Ph) HHH Ph -CH (4-Br-Ph) Me 1-68 4- (3-Tz-Ph) HHH Ph- CH (1-Np) Me 1-69 4- (4-Tz-Ph) HHH Ph 1-Inda 1-70 4- (4-Tz-Ph) HHH Ph -CH (4-Br-Ph) Me 1- 71 4- (4-Tz-Ph) HHH Ph -CH (1-Np) Me 1-72 2- (3-HO_ThreeS-Ph) H H H Ph 1-Et-Pn 1-73 2- (3-HO_ThreeS-Ph) H H H Ph cHx 1-74 2- (3-HO_ThreeS-Ph) H H H Ph -CH (Ph) Me 1-75 2- (2-MeSO_Two-Ph) H H H Ph iPr 1-76 2- (2-MeSO_Two-Ph) H H H Ph Bu 1-77 2- (2-MeSO_Two-Ph) H H H Ph tBu 1-78 2- (2-MeSO_Two-Ph) H H H Ph nPn 1-79 2- (2-MeSO_Two-Ph) H H H Ph 1-Et-Pn 1-80 2- (2-MeSO_Two-Ph) 4-Me H H Ph 1-Et-Pn 1-81 2- (2-MeSO_Two-Ph) 4-OMe H H Ph 1-Et-Pn 1-82 2- (2-MeSO_Two-Ph) 4-OMe 6-OH H Ph 1-Et-Pn 1-83 2- (2-MeSO_Two-Ph) 6-OMe H H Ph 1-Et-Pn 1-84 2- (2-MeSO_Two-Ph) 4-OH H H Ph 1-Et-Pn 1-85 2- (2-MeSO_Two-Ph) H H H Ph 2-Et-Hx 1-86 2- (2-MeSO_Two-Ph) H H H Ph cPn 1-87 2- (2-MeSO_Two-Ph) H H H Ph cHx 1-88 2- (2-MeSO_Two-Ph) H H H Ph 4-MeO-cHx 1-89 2- (2-MeSO_Two-Ph) H H H Ph 4-F-cHx 1-90 2- (2-MeSO_Two-Ph) H H H Ph 4-Cl-cHx 1-91 2- (2-MeSO_Two-Ph) H H H Ph 4-Me-cHx 1-92 2- (2-MeSO_Two-Ph) H H H Ph 4-tBu-cHx 1-93 2- (2-MeSO_Two-Ph) H H H Ph Bz 1-94 2- (2-MeSO_Two-Ph) H H H Ph-(CH_Two)_Two-Ph 1-95 2- (2-MeSO_Two-Ph) H H H Ph -CH (Ph) Me 1-96 2- (2-MeSO_Two-Ph) 4-Me H H Ph -CH (Ph) Me 1-97 2- (2-MeSO_Two-Ph) 4-OMe H H Ph -CH (Ph) Me 1-98 2- (2-MeSO_Two-Ph) 4-OMe 6-OH H Ph -CH (Ph) Me 1-99 2- (2-MeSO_Two-Ph) 6-OMe H H Ph -CH (Ph) Me 1-100 2- (2-MeSO_Two-Ph) 4-OH H H Ph -CH (Ph) Me 1-101 2- (2-MeSO_Two-Ph) H H H Ph 1-Inda 1-102 2- (2-MeSO_Two-Ph) H H H Ph -CH (4-Br-Ph) Me 1-103 2- (2-MeSO_Two-Ph) H H H Ph -CH (1-Np) Me 1-104 2- (3-MeSO_Two-Ph) H H H Ph tBu 1-105 2- (3-MeSO_Two-Ph) H H H Ph 1-Et-Pn 1-106 2- (3-MeSO_Two-Ph) H H H Ph 2-Et-Hx 1-107 2- (3-MeSO_Two-Ph) H H H Ph cHx 1-108 2- (3-MeSO_Two-Ph) H H H Ph -CH (4-Br-Ph) Me 1-109 2- (3-MeSO_Two-Ph) H H H Ph 4-Me-cHx 1-110 2- (3-MeSO_Two-Ph) H H H Ph Bz 1-111 2- (3-MeSO_Two-Ph) H H H Ph -CH (Ph) Me 1-112 2- (3-MeSO_Two-Ph) H H H Ph -CH (4-Me-Ph) Me 1-113 2- (4-MeSO_Two-Ph) H H H Ph iPr 1-114 2- (4-MeSO_Two-Ph) H H H Ph Bu 1-115 2- (4-MeSO_Two-Ph) H H H Ph tBu 1-116 2- (4-MeSO_Two-Ph) H H H Ph nPn 1-117 2- (4-MeSO_Two-Ph) H H H Ph 1-Et-Pn 1-118 2- (4-MeSO_Two-Ph) 4-Me H H Ph 1-Et-Pn 1-119 2- (4-MeSO_Two-Ph) 4-OMe H H Ph 1-Et-Pn 1-120 2- (4-MeSO_Two-Ph) 4-OMe 6-OH H Ph 1-Et-Pn 1-121 2- (4-MeSO_Two-Ph) 6-OMe H H Ph 1-Et-Pn 1-122 2- (4-MeSO_Two-Ph) 4-OH H H Ph 1-Et-Pn 1-123 2- (4-MeSO_Two-Ph) H H H Ph 2-Et-Hx 1-124 2- (4-MeSO_Two-Ph) H H H Ph cPn 1-125 2- (4-MeSO_Two-Ph) H H H Ph cHx 1-126 2- (4-MeSO_Two-Ph) H H H Ph 4-MeO-cHx 1-127 2- (4-MeSO_Two-Ph) H H H Ph 4-F-cHx 1-128 2- (4-MeSO_Two-Ph) H H H Ph 4-Cl-cHx 1-129 2- (4-MeSO_Two-Ph) H H H Ph 4-HO-cHx 1-130 2- (4-MeSO_Two-Ph) H H H Ph 4-Me-cHx 1-131 2- (4-MeSO_Two-Ph) H H H Ph 4-tBu-cHx 1-132 2- (4-MeSO_Two-Ph) H H H Ph Bz 1-133 2- (4-MeSO_Two-Ph) H H H Ph-(CH_Two)_Two-Ph 1-134 2- (4-MeSO_Two-Ph) H H H Ph -CH (Ph) Me 1-135 2- (4-MeSO_Two-Ph) 4-Me H H Ph -CH (Ph) Me 1-136 2- (4-MeSO_Two-Ph) 4-OMe H H Ph -CH (Ph) Me 1-137 2- (4-MeSO_Two-Ph) 4-OMe 6-OH H Ph -CH (Ph) Me 1-138 2- (4-MeSO_Two-Ph) 6-OMe H H Ph -CH (Ph) Me 1-139 2- (4-MeSO_Two-Ph) 4-OH H H Ph -CH (Ph) Me 1-140 2- (4-MeSO_Two-Ph) H H H Ph -CH (4-Br-Ph) Me 1-141 3- (2-MeSO_Two-Ph) H H H Ph tBu 1-142 3- (2-MeSO_Two-Ph) H H H Ph 1-Et-Pn 1-143 3- (2-MeSO_Two-Ph) H H H Ph 2-Et-Hx 1-144 3- (2-MeSO_Two-Ph) H H H Ph cHx 1-145 3- (2-MeSO_Two-Ph) H H H Ph 4-Me-cHx 1-146 3- (2-MeSO_Two-Ph) H H H Ph Bz 1-147 3- (2-MeSO_Two-Ph) H H H Ph -CH (Ph) Me 1-148 3- (2-MeSO_Two-Ph) H H H Ph -CH (4-Me-Ph) Me 1-149 3- (2-MeSO_Two-Ph) H H H Ph -CH (4-Br-Ph) Me 1-150 3- (3-MeSO_Two-Ph) H H H Ph 1-Et-Pn 1-151 3- (3-MeSO_Two-Ph) H H H Ph 2-Et-Hx 1-152 3- (3-MeSO_Two-Ph) H H H Ph cHx 1-153 3- (3-MeSO_Two-Ph) H H H Ph Bz 1-154 3- (3-MeSO_Two-Ph) H H H Ph -CH (Ph) Me 1-155 3- (4-MeSO_Two-Ph) H H H Ph tBu 1-156 3- (4-MeSO_Two-Ph) H H H Ph 1-Et-Pn 1-157 3- (4-MeSO_Two-Ph) H H H Ph 2-Et-Hx 1-158 3- (4-MeSO_Two-Ph) H H H Ph cHx 1-159 3- (4-MeSO_Two-Ph) H H H Ph 4-Me-cHx 1-160 3- (4-MeSO_Two-Ph) H H H Ph Bz 1-161 3- (4-MeSO_Two-Ph) H H H Ph -CH (Ph) Me 1-162 3- (4-MeSO_Two-Ph) H H H Ph -CH (4-Me-Ph) Me 1-163 3- (4-MeSO_Two-Ph) H H H Ph -CH (4-Br-Ph) Me 1-164 4- (2-MeSO_Two-Ph) H H H Ph iPr 1-165 4- (2-MeSO_Two-Ph) H H H Ph Bu 1-166 4- (2-MeSO_Two-Ph) H H H Ph tBu 1-167 4- (2-MeSO_Two-Ph) H H H Ph nPn 1-168 4- (2-MeSO_Two-Ph) H H H Ph 1-Et-Pn 1-169 4- (2-MeSO_Two-Ph) 2-Me H H Ph 1-Et-Pn 1-170 4- (2-MeSO_Two-Ph) 2-OMe H H Ph 1-Et-Pn 1-171 4- (2-MeSO_Two-Ph) 2-OMe 6-OH H Ph 1-Et-Pn 1-172 4- (2-MeSO_Two-Ph) 6-OMe H H Ph 1-Et-Pn 1-173 4- (2-MeSO_Two-Ph) 2-OH H H Ph 1-Et-Pn 1-174 4- (2-MeSO_Two-Ph) H H H Ph 2-Et-Hx 1-175 4- (2-MeSO_Two-Ph) H H H Ph cPn 1-176 4- (2-MeSO_Two-Ph) H H H Ph cHx 1-177 4- (2-MeSO_Two-Ph) H H H Ph 4-MeO-cHx 1-178 4- (2-MeSO_Two-Ph) H H H Ph 4-F-cHx 1-179 4- (2-MeSO_Two-Ph) H H H Ph 4-Cl-cHx 1-180 4- (2-MeSO_Two-Ph) H H H Ph 4-HO-cHx 1-181 4- (2-MeSO_Two-Ph) H H H Ph 4-Me-cHx 1-182 4- (2-MeSO_Two-Ph) H H H Ph 4-tBu-cHx 1-183 4- (2-MeSO_Two-Ph) H H H Ph Bz 1-184 4- (2-MeSO_Two-Ph) H H H Ph-(CH_Two)_Two-Ph 1-185 4- (2-MeSO_Two-Ph) H H H Ph -CH (Ph) Me 1-186 4- (2-MeSO_Two-Ph) 2-Me H H Ph -CH (Ph) Me 1-187 4- (2-MeSO_Two-Ph) 2-OMe H H Ph -CH (Ph) Me 1-188 4- (2-MeSO_Two-Ph) 2-OMe 6-OH H Ph -CH (Ph) Me 1-189 4- (2-MeSO_Two-Ph) 6-OMe H H Ph -CH (Ph) Me 1-190 4- (2-MeSO_Two-Ph) 2-OH H H Ph -CH (Ph) Me 1-191 4- (2-MeSO_Two-Ph) H H H Ph 1-Inda 1-192 4- (2-MeSO_Two-Ph) H H H Ph -CH (4-Br-Ph) Me 1-193 4- (2-MeSO_Two-Ph) H H H Ph -CH (1-Np) Me 1-194 4- (3-MeSO_Two-Ph) H H H Ph tBu 1-195 4- (3-MeSO_Two-Ph) H H H Ph 1-Et-Pn 1-196 4- (3-MeSO_Two-Ph) H H H Ph 2-Et-Hx 1-197 4- (3-MeSO_Two-Ph) H H H Ph cHx 1-198 4- (3-MeSO_Two-Ph) H H H Ph 4-Me-cHx 1-199 4- (3-MeSO_Two-Ph) H H H Ph Bz 1-200 4- (3-MeSO_Two-Ph) H H H Ph -CH (Ph) Me 1-201 4- (3-MeSO_Two-Ph) H H H Ph -CH (4-Me-Ph) Me 1-202 4- (3-MeSO_Two-Ph) H H H Ph -CH (4-Br-Ph) Me 1-203 4- (4-MeSO_Two-Ph) H H H Ph iPr 1-204 4- (4-MeSO_Two-Ph) H H H Ph Bu 1-205 4- (4-MeSO_Two-Ph) H H H Ph tBu 1-206 4- (4-MeSO_Two-Ph) H H H Ph nPn 1-207 4- (4-MeSO_Two-Ph) H H H Ph 1-Et-Pn 1-208 4- (4-MeSO_Two-Ph) 2-Me H H Ph 1-Et-Pn 1-209 4- (4-MeSO_Two-Ph) 2-OMe H H Ph 1-Et-Pn 1-210 4- (4-MeSO_Two-Ph) 2-OMe 6-OH H Ph 1-Et-Pn 1-211 4- (4-MeSO_Two-Ph) 6-OMe H H Ph 1-Et-Pn 1-212 4- (4-MeSO_Two-Ph) 2-OH H H Ph 1-Et-Pn 1-213 4- (4-MeSO_Two-Ph) H H H Ph 2-Et-Hx 1-214 4- (4-MeSO_Two-Ph) H H H Ph cPn 1-215 4- (4-MeSO_Two-Ph) H H H Ph cHx 1-216 4- (4-MeSO_Two-Ph) H H H Ph 4-MeO-cHx 1-217 4- (4-MeSO_Two-Ph) H H H Ph 4-F-cHx 1-218 4- (4-MeSO_Two-Ph) H H H Ph 4-Cl-cHx 1-219 4- (4-MeSO_Two-Ph) H H H Ph 4-HO-cHx 1-220 4- (4-MeSO_Two-Ph) H H H Ph 4-Me-cHx 1-221 4- (4-MeSO_Two-Ph) H H H Ph 4-tBu-cHx 1-222 4- (4-MeSO_Two-Ph) H H H Ph Bz 1-223 4- (4-MeSO_Two-Ph) H H H Ph-(CH_Two)_Two-Ph 1-224 4- (4-MeSO_Two-Ph) H H H Ph -CH (Ph) Me 1-225 4- (4-MeSO_Two-Ph) 2-Me H H Ph -CH (Ph) Me 1-226 4- (4-MeSO_Two-Ph) 2-OMe H H Ph -CH (Ph) Me 1-227 4- (4-MeSO_Two-Ph) 2-OMe 6-OH H Ph -CH (Ph) Me 1-228 4- (4-MeSO_Two-Ph) 6-OMe H H Ph -CH (Ph) Me 1-229 4- (4-MeSO_Two-Ph) 2-OH H H Ph -CH (Ph) Me 1-230 4- (4-MeSO_Two-Ph) H H H Ph 1-Inda 1-231 4- (4-MeSO_Two-Ph) H H H Ph -CH (4-Br-Ph) Me 1-232 4- (4-MeSO_Two-Ph) H H H Ph -CH (1-Np) Me 1-233 2- (2-EtSO_Two-Ph) H H H Ph tBu 1-234 2- (2-EtSO_Two-Ph) H H H Ph 1-Et-Pn 1-235 2- (2-EtSO_Two-Ph) H H H Ph 2-Et-Hx 1-236 2- (2-EtSO_Two-Ph) H H H Ph cHx 1-237 2- (2-EtSO_Two-Ph) H H H Ph 4-Me-cHx 1-238 2- (2-EtSO_Two-Ph) H H H Ph Bz 1-239 2- (2-EtSO_Two-Ph) H H H Ph -CH (Ph) Me 1-240 2- (2-EtSO_Two-Ph) H H H Ph -CH (Br-Ph) Me 1-241 2- (3-EtSO_Two-Ph) H H H Ph 1-Et-Pn 1-242 2- (3-EtSO_Two-Ph) H H H Ph 2-Et-Hx 1-243 2- (3-EtSO_Two-Ph) H H H Ph cHx 1-244 2- (3-EtSO_Two-Ph) H H H Ph Bz 1-245 2- (3-EtSO_Two-Ph) H H H Ph -CH (Ph) Me 1-246 2- (4-EtSO_Two-Ph) H H H Ph tBu 1-247 2- (4-EtSO_Two-Ph) H H H Ph 1-Et-Pn 1-248 2- (4-EtSO_Two-Ph) H H H Ph 2-Et-Hx 1-249 2- (4-EtSO_Two-Ph) H H H Ph cHx 1-250 2- (4-EtSO_Two-Ph) H H H Ph 4-Me-cHx 1-251 2- (4-EtSO_Two-Ph) H H H Ph Bz 1-252 2- (4-EtSO_Two-Ph) H H H Ph -CH (Ph) Me 1-253 2- (4-EtSO_Two-Ph) H H H Ph -CH (4-Me-Ph) Me 1-255 3- (2-EtSO_Two-Ph) H H H Ph cHx 1-256 3- (2-EtSO_Two-Ph) H H H Ph 1-Et-Pn 1-257 3- (2-EtSO_Two-Ph) H H H Ph -CH (Ph) Me 1-258 3- (3-EtSO_Two-Ph) H H H Ph cHx 1-259 3- (3-EtSO_Two-Ph) H H H Ph 1-Et-Pn 1-260 3- (3-EtSO_Two-Ph) H H H Ph -CH (Ph) Me 1-261 3- (4-EtSO_Two-Ph) H H H Ph cHx 1-262 3- (4-EtSO_Two-Ph) H H H Ph 1-Et-Pn 1-263 3- (4-EtSO_Two-Ph) H H H Ph -CH (Ph) Me 1-264 4- (2-EtSO_Two-Ph) H H H Ph 1-Et-Pn 1-265 4- (2-EtSO_Two-Ph) H H H Ph 2-Et-Hx 1-266 4- (2-EtSO_Two-Ph) H H H Ph cHx 1-267 4- (2-EtSO_Two-Ph) H H H Ph Bz 1-268 4- (2-EtSO_Two-Ph) H H H Ph -CH (Ph) Me 1-269 4- (3-EtSO_Two-Ph) H H H Ph 1-Et-Pn 1-270 4- (3-EtSO_Two-Ph) H H H Ph cHx 1-271 4- (3-EtSO_Two-Ph) H H H Ph -CH (Ph) Me 1-272 4- (4-EtSO_Two-Ph) H H H Ph 1-Et-Pn 1-273 4- (4-EtSO_Two-Ph) H H H Ph 2-Et-Hx 1-274 4- (4-EtSO_Two-Ph) H H H Ph cHx 1-275 4- (4-EtSO_Two-Ph) H H H Ph Bz 1-276 4- (4-EtSO_Two-Ph) H H H Ph -CH (Ph) Me 1-277 2- (2-PrSO_Two-Ph) H H H Ph 1-Et-Pn 1-278 2- (2-PrSO_Two-Ph) H H H Ph 2-Et-Hx 1-279 2- (2-PrSO_Two-Ph) H H H Ph cHx 1-280 2- (2-PrSO_Two-Ph) H H H Ph Bz 1-281 2- (2-PrSO_Two-Ph) H H H Ph -CH (Ph) Me 1-282 2- (3-PrSO_Two-Ph) H H H Ph 1-Et-Pn 1-283 2- (3-PrSO_Two-Ph) H H H Ph cHx 1-284 2- (3-PrSO_Two-Ph) H H H Ph -CH (Ph) Me 1-285 2- (4-PrSO_Two-Ph) H H H Ph 1-Et-Pn 1-286 2- (4-PrSO_Two-Ph) H H H Ph 2-Et-Hx 1-287 2- (4-PrSO_Two-Ph) H H H Ph cHx 1-288 2- (4-PrSO_Two-Ph) H H H Ph Bz 1-289 2- (4-PrSO_Two-Ph) H H H Ph -CH (Ph) Me 1-290 3- (2-PrSO_Two-Ph) H H H Ph 1-Et-Pn 1-291 3- (2-PrSO_Two-Ph) H H H Ph cHx 1-292 3- (2-PrSO_Two-Ph) H H H Ph -CH (Ph) Me 1-293 3- (3-PrSO_Two-Ph) H H H Ph cHx 1-294 3- (4-PrSO_Two-Ph) H H H Ph 1-Et-Pn 1-295 3- (4-PrSO_Two-Ph) H H H Ph cHx 1-296 3- (4-PrSO_Two-Ph) H H H Ph -CH (Ph) Me 1-297 4- (2-PrSO_Two-Ph) H H H Ph 1-Et-Pn 1-298 4- (2-PrSO_Two-Ph) H H H Ph cHx 1-299 4- (2-PrSO_Two-Ph) H H H Ph -CH (Ph) Me 1-300 4- (3-PrSO_Two-Ph) H H H Ph cHx 1-301 4- (4-PrSO_Two-Ph) H H H Ph 1-Et-Pn 1-302 4- (4-PrSO_Two-Ph) H H H Ph cHx 1-303 4- (4-PrSO_Two-Ph) H H H Ph -CH (Ph) Me 1-304 2- (2-BuSO_Two-Ph) H H H Ph 1-Et-Pn 1-305 2- (2-BuSO_Two-Ph) H H H Ph cHx 1-306 2- (2-BuSO_Two-Ph) H H H Ph -CH (Ph) Me 1-307 2- (4-BuSO_Two-Ph) H H H Ph 1-Et-Pn 1-308 2- (4-BuSO_Two-Ph) H H H Ph cHx 1-309 2- (4-BuSO_Two-Ph) H H H Ph -CH (Ph) Me 1-310 2- (2-MeSO_TwoHN-Ph) H H H Ph 1-Et-Pn 1-311 2- (2-MeSO_TwoHN-Ph) H H H Ph cHx 1-312 2- (2-MeSO_TwoHN-Ph) H H H Ph -CH (Ph) Me 1-313 2- (4-MeSO_TwoHN-Ph) H H H Ph 1-Et-Pn 1-314 2- (4-MeSO_TwoHN-Ph) H H H Ph cHx 1-315 2- (4-MeSO_TwoHN-Ph) H H H Ph -CH (Ph) Me 1-316 4- (2-MeSO_TwoHN-Ph) H H H Ph 1-Et-Pn 1-317 4- (2-MeSO_TwoHN-Ph) H H H Ph cHx 1-318 4- (2-MeSO_TwoHN-Ph) H H H Ph -CH (Ph) Me 1-319 4- (4-MeSO_TwoHN-Ph) H H H Ph 1-Et-Pn 1-320 4- (4-MeSO_TwoHN-Ph) H H H Ph cHx 1-321 4- (4-MeSO_TwoHN-Ph) H H H Ph -CH (Ph) Me 1-322 2- (2-EtSO_TwoHN-Ph) H H H Ph 1-Et-Pn 1-323 2- (2-EtSO_TwoHN-Ph) H H H Ph cHx 1-324 2- (2-EtSO_TwoHN-Ph) H H H Ph -CH (Ph) Me 1-325 2- (4-EtSO_TwoHN-Ph) H H H Ph 1-Et-Pn 1-326 2- (4-EtSO_TwoHN-Ph) H H H Ph cHx 1-327 2- (4-EtSO_TwoHN-Ph) H H H Ph -CH (Ph) Me 1-328 4- (2-EtSO_TwoHN-Ph) H H H Ph 1-Et-Pn 1-329 4- (2-EtSO_TwoHN-Ph) H H H Ph cHx 1-330 4- (2-EtSO_TwoHN-Ph) H H H Ph -CH (Ph) Me 1-331 4- (4-EtSO_TwoHN-Ph) H H H Ph 1-Et-Pn 1-332 4- (4-EtSO_TwoHN-Ph) H H H Ph cHx 1-333 4- (4-EtSO_TwoHN-Ph) H H H Ph -CH (Ph) Me 1-334 2- [4- (2-Tol) SO_TwoHN-Ph] H H H Ph cHx 1-335 2- [4- (3-Tol) SO_TwoHN-Ph] H H H Ph cHx 1-336 2- [4- (4-Tol) SO_TwoHN-Ph] H H H Ph 1-Et-Pn 1-337 2- [4- (4-Tol) SO_TwoHN-Ph] H H H Ph cHx 1-338 2- [4- (4-Tol) SO_TwoHN-Ph] H H H Ph 4-Me-cHx 1-339 2- [4- (4-Tol) SO_TwoHN-Ph] H H H Ph -CH (Ph) Me 1-340 3- [4- (4-Tol) SO_TwoHN-Ph] H H H Ph cHx 1-342 2- [4- (4-MeO-Ph) SO_TwoHN-Ph] H H H Ph cHx 1-343 2- [4- (4-F-Ph) SO_TwoHN-Ph] H H H Ph cHx 1-344 2- [4- (4-Cl-Ph) SO_TwoHN-Ph] HHH Ph cHx 1-345 2- (3-Tz-Ph) HHH 4-Me-Ph cHx 1-346 3- (3-Tz-Ph) HHH 4-Me-Ph 1-Et-Pn 1 -347 4- (2-Tz-Ph) HHH 4-Me-Ph -CH (Ph) Me 1-348 4- (3-Tz-Ph) HHH 4-Me-Ph 1-Et-Pn 1-349 2 -(2-MeSO_Two-Ph) H H H 4-Me-Ph -CH (Ph) Me 1-350 2- (3-MeSO_Two-Ph) H H H 4-Me-Ph cHx 1-351 2- (4-MeSO_Two-Ph) H H H 4-Me-Ph cHx 1-352 3- (2-MeSO_Two-Ph) H H H 4-Me-Ph cHx 1-353 3- (4-MeSO_Two-Ph) H H H 4-Me-Ph cHx 1-354 4- (2-MeSO_Two-Ph) H H H 4-Me-Ph -CH (Ph) Me 1-355 4- (3-MeSO_Two-Ph) H H H 4-Me-Ph cHx 1-356 4- (4-MeSO_Two-Ph) H H H 4-Me-Ph -CH (Ph) Me 1-357 2- (2-EtSO_Two-Ph) H H H 4-Me-Ph cHx 1-358 2- (4-EtSO_Two-Ph) HHH 4-Me-Ph cHx 1-359 2-Tz HHH Ph iPr 1-360 2-Tz HHH Ph Bu 1-361 2-Tz HHH Ph tBu 1-362 2-Tz HHH Ph nPn 1-363 2 -Tz HHH Ph 2-Hx 1-364 2-Tz HHH Ph 1-Et-Pn 1-365 2-Tz 4-Me HH Ph 1-Et-Pn 1-366 2-Tz 4-OMe HH Ph 1-Et -Pn 1-367 2-Tz 4-OMe 6-OH H Ph 1-Et-Pn 1-368 2-Tz 4-OMe 5-F 6-OH Ph 1-Et-Pn 1-369 2-Tz 6- OMe HH Ph 1-Et-Pn 1-370 2-Tz 4-OH HH Ph 1-Et-Pn 1-371 2-Tz 4-FHH Ph 1-Et-Pn 1-372 2-Tz 4-Cl HH Ph 1-Et-Pn 1-373 2-Tz 4-NH_Two H H Ph 1-Et-Pn 1-374 2-Tz 4-NHMe H H Ph 1-Et-Pn 1-375 2-Tz 4-N (Me)_Two HH Ph 1-Et-Pn 1-376 2-Tz HHH 2-Me-Ph 1-Et-Pn 1-377 2-Tz HHH 3-Me-Ph 1-Et-Pn 1-378 2-Tz HHH 4- Me-Ph 1-Et-Pn 1-379 2-Tz HHH 4-MeO-Ph 1-Et-Pn 1-380 2-Tz HHH 4-F-Ph 1-Et-Pn 1-381 2-Tz HHH 4 -Cl-Ph 1-Et-Pn 1-382 2-Tz HHH 1-Et-Pn R^5a= 4-Me-2-MeO-Ph 1-383 2-Tz H H H 1-Et-Pn R^5a= 4-Me-6-F-2-MeO-Ph 1-384 2-Tz HHH Ph 2-Et-Hx 1-385 2-Tz HHH Ph cPn 1-386 2-Tz HHH Ph cHx 1-387 2- Tz 4-Me HH Ph cHx 1-388 2-Tz 4-OMe HH Ph cHx 1-389 2-Tz 4-OMe 6-OH H Ph cHx 1-390 2-Tz 6-OMe HH Ph cHx 1-391 2 -Tz 4-OH HH Ph cHx 1-392 2-Tz HHH Ph 4-Me-cHx 1-393 2-Tz HHH Ph 4-tBu-cHx 1-395 2-Tz HHH Ph 4-F-cHx 1-396 2-Tz HHH Ph 4-Cl-cHx 1-397 2-Tz HHH Ph 4-HO-cHx 1-398 2-Tz HHH Ph 4-HOH_TwoC-cHx 1-399 2-Tz H H H Ph -CH_Two-(4-HOH_TwoC-cHx) 1-400 2-Tz H H H Ph -CH_Two-(4-HOOC-cHx) 1-401 2-Tz H H H Ph -CH_Two-[4- (Me)_TwoNOC-cHx] 1-402 2-Tz H H H Ph 1-Inda 1-403 2-Tz H H H Ph Bz 1-404 2-Tz H H H Ph 4-Me-Bz 1-405 2-Tz H H H Ph-(CH_Two)_Two-Ph 1-406 2-Tz HHH Ph -CH (Ph) Me 1-407 2-Tz HHH 2-Me-Ph -CH (Ph) Me 1-408 2-Tz HHH 3-Me-Ph -CH (Ph ) Me 1-409 2-Tz HHH 4-Me-Ph -CH (Ph) Me 1-410 2-Tz HHH 4-MeO-Ph -CH (Ph) Me 1-411 2-Tz HHH 4-F-Ph -CH (Ph) Me 1-412 2-Tz HHH 4-Cl-Ph -CH (Ph) Me 1-413 2-Tz HHH -CH (Ph) Me R^5a= 2-MeO-4-Me-Ph 1-414 2-Tz H H H -CH (Ph) Me R^5a= 6-F-4-Me-2-MeO-Ph 1-415 2-Tz 4-Me HH Ph -CH (Ph) Me 1-416 2-Tz 4-OMe HH Ph -CH (Ph) Me 1- 417 2-Tz 4-OMe 6-OH H Ph -CH (Ph) Me 1-418 2-Tz 4-OMe 5-F 6-OH Ph -CH (Ph) Me 1-419 2-Tz 6-OMe HH Ph -CH (Ph) Me 1-420 2-Tz 4-OH HH Ph -CH (Ph) Me 1-421 2-Tz 4-FHH Ph -CH (Ph) Me 1-422 2-Tz 4-Cl HH Ph -CH (Ph) Me 1-423 2-Tz 4-NH_Two H H Ph -CH (Ph) Me 1-424 2-Tz 4-NHMe H H Ph -CH (Ph) Me 1-425 2-Tz 4-N (Me)_Two HH Ph -CH (Ph) Me 1-426 2-Tz HHH Ph -CH (4-Me-Ph) Me 1-427 2-Tz HHH Ph -CH (4-MeO-Ph) Me 1-428 2-Tz HHH Ph -CH (4-F-Ph) Me 1-429 2-Tz HHH Ph -CH (4-Cl-Ph) Me 1-430 2-Tz HHH Ph 3-Pn 1-431 2-Tz HHH 4- Me-Ph 3-Pn 1-432 2-Tz HHH Ph -CH (cHx) Me 1-433 2-Tz HHH 4-Me-Ph -CH (cHx) Me 1-434 2-Tz HHH Ph -CH (4 -Br-Ph) Me 1-435 2-Tz HHH 4-Me-Ph -CH (4-Br-Ph) Me 1-436 2-Tz 4-Me HH Ph -CH (4-Br-Ph) Me 1 -437 2-Tz 4-FHH Ph -CH (4-Br-Ph) Me 1-438 2-Tz HHH Ph -CH_Two(4-H_TwoNOC-Ph) 1-439 2-Tz H H H 4-Me-Ph -CH_Two(4-H_TwoNOC-Ph) 1-440 2-Tz HHH Ph -CH (1-Np) Me 1-441 2-Tz HHH 4-Me-Ph -CH (1-Np) Me 1-442 3-Tz HHH Ph iPr 1 -443 3-Tz HHH Ph Bu 1-444 3-Tz HHH Ph tBu 1-445 3-Tz HHH Ph nPn 1-446 3-Tz HHH Ph 2-Hx 1-447 3-Tz HHH Ph 1-Et-Pn 1-448 3-Tz 4-Me HH Ph 1-Et-Pn 1-449 3-Tz 4-OMe HH Ph 1-Et-Pn 1-450 3-Tz 4-OMe 6-OH H Ph 1-Et- Pn 1-451 3-Tz 4-OMe 5-F 6-OH Ph 1-Et-Pn 1-452 3-Tz 6-OMe HH Ph 1-Et-Pn 1-453 3-Tz 4-OH HH Ph 1 -Et-Pn 1-454 3-Tz 4-FHH Ph 1-Et-Pn 1-455 3-Tz 4-Cl HH Ph 1-Et-Pn 1-456 3-Tz 4-NH_Two H H Ph 1-Et-Pn 1-457 3-Tz 4-NHMe H H Ph 1-Et-Pn 1-458 3-Tz 4-N (Me)_Two HH Ph 1-Et-Pn 1-459 3-Tz HHH 2-Me-Ph 1-Et-Pn 1-460 3-Tz HHH 3-Me-Ph 1-Et-Pn 1-461 3-Tz HHH 4- Me-Ph 1-Et-Pn 1-462 3-Tz HHH 4-MeO-Ph 1-Et-Pn 1-463 3-Tz HHH 4-F-Ph 1-Et-Pn 1-464 3-Tz HHH 4 -Cl-Ph 1-Et-Pn 1-465 3-Tz HHH 1-Et-Pn R^5a= 4-Me-2-MeO-Ph 1-466 3-Tz H H H 1-Et-Pn R^5a= 6-F-4-Me-2-MeO-Ph 1-467 3-Tz HHH Ph 2-Et-Hx 1-468 3-Tz HHH Ph cPn 1-469 3-Tz HHH Ph cHx 1-470 3- Tz 4-Me HH Ph cHx 1-471 3-Tz 4-OMe HH Ph cHx 1-472 3-Tz 4-OMe 6-OH H Ph cHx 1-473 3-Tz 6-OMe HH Ph cHx 1-474 3 -Tz 4-OH HH Ph cHx 1-475 3-Tz HHH Ph 4-Me-cHx 1-476 3-Tz HHH Ph 4-tBu-cHx 1-478 3-Tz HHH Ph 4-F-cHx 1-479 3-Tz HHH Ph 4-Cl-cHx 1-480 3-Tz HHH Ph 4-HO-cHx 1-481 3-Tz HHH Ph 4-HOH_TwoC-cHx 1-482 3-Tz H H H Ph -CH_Two-(4-HOH_TwoC-cHx) 1-483 3-Tz H H H Ph -CH_Two-(4-HOOC-cHx) 1-484 3-Tz H H H Ph -CH_Two-[4- (Me)_TwoNOC-cHx] 1-485 3-Tz H H H Ph 1-Inda 1-486 3-Tz H H H Ph Bz 1-487 3-Tz H H H Ph 4-Me-Bz 1-488 3-Tz H H H Ph-(CH_Two)_Two-Ph 1-489 3-Tz HHH Ph -CH (Ph) Me 1-490 3-Tz 4-Me HH Ph -CH (Ph) Me 1-491 3-Tz 4-OMe HH Ph -CH (Ph) Me 1-492 3-Tz 4-OMe 6-OH H Ph -CH (Ph) Me 1-493 3-Tz 4-OMe 5-F 6-OH Ph -CH (Ph) Me 1-494 3-Tz 6- OMe HH Ph -CH (Ph) Me 1-495 3-Tz 4-OH HH Ph -CH (Ph) Me 1-496 3-Tz 6-FHH Ph -CH (Ph) Me 1-497 3-Tz 4- Cl HH Ph -CH (Ph) Me 1-498 3-Tz 4-NH_Two H H Ph -CH (Ph) Me 1-499 3-Tz 4-NHMe H H Ph -CH (Ph) Me 1-500 3-Tz 4-N (Me)_Two HH Ph -CH (Ph) Me 1-501 3-Tz HHH 2-Me-Ph -CH (Ph) Me 1-502 3-Tz HHH 3-Me-Ph -CH (Ph) Me 1-503 3-Tz HHH 4-Me-Ph -CH (Ph) Me 1-504 3-Tz HHH 4-MeO-Ph -CH (Ph) Me 1-505 3-Tz HHH 4-F-Ph -CH (Ph) Me 1- 506 3-Tz HHH 4-Cl-Ph -CH (Ph) Me 1 -507 3-Tz HHH -CH (Ph) Me R^5a= 4-Me-2-MeO-Ph 1-508 3-Tz H H H -CH (Ph) Me R^5a= 6-F-4-Me-2-MeO-Ph 1-509 3-Tz HHH Ph -CH (4-Me-Ph) Me 1-510 3-Tz HHH Ph -CH (4-MeO-Ph) Me 1-511 3-Tz HHH Ph -CH (4-F-Ph) Me 1-512 3-Tz HHH Ph -CH (4-Cl-Ph) Me 1-513 3-Tz HHH Ph 3-Pn 1-514 3-Tz HHH 4-Me-Ph 3-Pn 1-515 3-Tz HHH Ph -CH (cHx) Me 1-516 3-Tz HHH 4-Me-Ph -CH (cHx) Me 1-517 3-Tz HHH Ph -CH (4-Br-Ph) Me 1-518 3-Tz HHH 4-Me-Ph -CH (4-Br-Ph) Me 1-519 3-Tz 4-Me HH Ph -CH (4- (Br-Ph) Me 1-520 3-Tz 4-FHH Ph -CH (4-Br-Ph) Me 1-521 3-Tz HHH Ph -CH_Two(4-H_TwoNOC-Ph) 1-522 3-Tz H H H 4-Me-Ph -CH_Two(4-H_TwoNOC-Ph) 1-523 3-Tz HHH Ph -CH (1-Np) Me 1-524 3-Tz HHH 4-Me-Ph -CH (1-Np) Me 1-525 4-Tz HHH Ph iPr 1 -526 4-Tz HHH Ph Bu 1-527 4-Tz HHH Ph tBu 1-528 4-Tz HHH Ph nPn 1-529 4-Tz HHH Ph 2-Hx 1-530 4-Tz HHH Ph 1-Et-Pn 1-531 4-Tz 2-Me HH Ph 1-Et-Pn 1-532 4-Tz 2-OMe HH Ph 1-Et-Pn 1-533 4-Tz 2-OMe 6-OH H Ph 1-Et- Pn 1-534 4-Tz 2-OMe 5-F 6-OH Ph 1-Et-Pn 1-535 4-Tz 6-OMe HH Ph 1-Et-Pn 1-536 4-Tz 2-OH HH Ph 1 -Et-Pn 1-537 4-Tz 2-FHH Ph 1-Et-Pn 1-538 4-Tz 2-Cl HH Ph 1-Et-Pn 1-539 4-Tz 2-NH_Two H H Ph 1-Et-Pn 1-540 4-Tz 2-NHMe H H Ph 1-Et-Pn 1-541 4-Tz 2-N (Me)_Two HH Ph 1-Et-Pn 1-542 4-Tz HHH 2-Me-Ph 1-Et-Pn 1-543 4-Tz HHH 3-Me-Ph 1-Et-Pn 1-544 4-Tz HHH 4- Me-Ph 1-Et-Pn 1-545 4-Tz HHH 4-MeO-Ph 1-Et-Pn 1-546 4-Tz HHH 4-F-Ph 1-Et-Pn 1-547 4-Tz HHH 4 -Cl-Ph 1-Et-Pn 1-548 4-Tz HHH 1-Et-Pn R^5a= 4-Me-2-MeO-Ph 1-549 4-Tz H H H 1-Et-Pn R^5a= 6-F-4-Me-2-MeO-Ph 1-550 4-Tz HHH Ph 2-Et-Hx 1-551 4-Tz HHH Ph cPn 1-552 4-Tz HHH Ph cHx 1-553 4- Tz 2-Me HH Ph cHx 1-554 4-Tz 2-OMe HH Ph cHx 1-555 4-Tz 2-OMe 6-OH H Ph cHx 1-556 4-Tz 6-OMe HH Ph cHx 1-557 4 -Tz 2-OH HH Ph cHx 1-558 4-Tz HHH Ph 4-Me-cHx 1-559 4-Tz HHH Ph 4-tBu-cHx 1-560 4-Tz HHH Ph 4-MeO-cHx 1-561 4-Tz HHH Ph 4-F-cHx 1-562 4-Tz HHH Ph 4-Cl-cHx 1-563 4-Tz HHH Ph 4-HO-cHx 1-564 4-Tz HHH Ph 4-HOH_TwoC-cHx 1-565 4-Tz H H H Ph -CH_Two-(4-HOH_TwoC-cHx) 1-566 4-Tz H H H Ph -CH_Two-(4-HOOC-cHx) 1-567 4-Tz H H H Ph -CH_Two-[4- (Me)_TwoNOC-cHx] 1-568 4-Tz H H H Ph 1-Inda 1-569 4-Tz H H H Ph Bz 1-570 4-Tz H H H Ph 4-Me-Bz 1-571 4-Tz H H H Ph-(CH_Two)_Two-Ph 1-572 4-Tz HHH Ph -CH (Ph) Me 1-573 4-Tz 2-Me HH Ph -CH (Ph) Me 1-574 4-Tz 2-OMe HH Ph -CH (Ph) Me 1-575 4-Tz 2-OMe 6-OH H Ph -CH (Ph) Me 1-576 4-Tz 2-OMe 5-F 6-OH Ph -CH (Ph) Me 1-577 4-Tz 6- OMe HH Ph -CH (Ph) Me 1-578 4-Tz 2-OH HH Ph -CH (Ph) Me 1-579 4-Tz 2-FHH Ph -CH (Ph) Me 1-580 4-Tz 2- Cl HH Ph -CH (Ph) Me 1-581 4-Tz 2-NH_Two H H Ph -CH (Ph) Me 1-582 4-Tz 2-NHMe H H Ph -CH (Ph) Me 1-583 4-Tz 2-N (Me)_Two HH Ph -CH (Ph) Me 1-584 4-Tz HHH 2-Me-Ph -CH (Ph) Me 1-585 4-Tz HHH 3-Me-Ph -CH (Ph) Me 1-586 4-Tz HHH 4-Me-Ph -CH (Ph) Me 1-587 4-Tz HHH 4-MeO-Ph -CH (Ph) Me 1-588 4-Tz HHH 4-F-Ph -CH (Ph) Me 1- 589 4-Tz HHH 4-Cl-Ph -CH (Ph) Me 1-590 4-Tz HHH -CH (Ph) Me R^5a= 4-Me-2-MeO-Ph 1-591 4-Tz H H H -CH (Ph) Me R^5a= 6-F-4-Me-2-MeO-Ph 1-592 4-Tz HHH Ph -CH (4-Me-Ph) Me 1-593 4-Tz HHH Ph -CH (4-MeO-Ph) Me 1-594 4-Tz HHH Ph -CH (4-F-Ph) Me 1-595 4-Tz HHH Ph -CH (4-Cl-Ph) Me 1-596 4-Tz HHH Ph 3-Pn 1-597 4-Tz HHH 4-Me-Ph 3-Pn 1-598 4-Tz HHH Ph -CH (cHx) Me 1-599 4-Tz HHH 4-Me-Ph -CH (cHx) Me 1-600 4-Tz HHH Ph -CH (4-Br-Ph) Me 1-601 4-Tz HHH 4-Me-Ph -CH (4-Br-Ph) Me 1-602 4-Tz 2-Me HH Ph -CH (4- Br-Ph) Me 1-603 4-Tz 2-FHH Ph -CH (4-Br-Ph) Me 1-604 4-Tz HHH Ph -CH_Two(4-H_TwoNOC-Ph) 1-605 4-Tz H H H 4-Me-Ph -CH_Two(4-H_TwoNOC-Ph) 1-606 4-Tz HHH Ph -CH (1-Np) Me 1-607 4-Tz HHH 4-Me-Ph -CH (1-Np) Me 1-608 2-Tz 4-Me HH Ph -CH (cHx) Me 1-609 2-Tz 4-FHH Ph -CH (cHx) Me 1-610 2-Tz 4-OMe HH Ph -CH (4-Br-Ph) Me 1-611 2-Tz 6-OMe HH Ph -CH (4-Br-Ph) Me 1-612 2-Tz 4-Me HH Ph -CH (1-Np) Me 1-613 2-Tz 4-FHH Ph -CH (1-Np ) Me 1-614 3-Tz 4-Me HH Ph -CH (cHx) Me 1-615 3-Tz 4-FHH Ph -CH (cHx) Me 1-616 3-Tz 4-OMe HH Ph -CH (4 -Br-Ph) Me 1-617 3-Tz 6-OMe HH Ph -CH (4-Br-Ph) Me 1-618 3-Tz 4-Me HH Ph -CH (1-Np) Me 1-6193 -Tz 4-FHH Ph -CH (1-Np) Me 1-620 4-Tz 2-Me HH Ph -CH (cHx) Me 1-621 4-Tz 2-FHH Ph -CH (cHx) Me 1-622 4-Tz 2-OMe HH Ph -CH (4-Br-Ph) Me 1-623 4-Tz 6-OMe HH Ph -CH (4-Br-Ph) Me 1-624 4-Tz 2-Me HH Ph -CH (1-Np) Me 1-625 4-Tz 2-FHH Ph -CH (1-Np) Me 1-626 2- (cPn) HNOC HHH Ph cHx 1-627 2- (cHx) HNOC HHH Ph 1 -Et-Pn 1-628 2- (cHx) HNOC HHH Ph cHx 1-629 2- (cHx) HNOC HHH Ph CH_Two(Ph) Me 1-630 2- (cHx) HNOC H H H 4-Me-Ph cHx 1-631 3- (cHx) HNOC H H H Ph cHx 1-632 4- (cHx) HNOC H H H Ph cHx 1-633 2-MeSO_TwoHNOC H H H Ph 1-Et-Pn 1-634 2-MeSO_TwoHNOC H H H Ph 2-Et-Hx 1-635 2-MeSO_TwoHNOC H H H Ph cHx 1-636 2-MeSO_TwoHNOC H H H Ph Bz 1-637 2-MeSO_TwoHNOC H H H Ph -CH (Ph) Me 1-638 3-MeSO_TwoHNOC H H H Ph 1-Et-Pn 1-639 3-MeSO_TwoHNOC H H H Ph cHx 1-640 3-MeSO_TwoHNOC H H H Ph -CH (Ph) Me 1-641 4-MeSO_TwoHNOC H H H Ph 1-Et-Pn 1-642 4-MeSO_TwoHNOC H H H Ph cHx 1-643 4-MeSO_TwoHNOC H H H Ph -CH (Ph) Me 1-644 2-EtSO_TwoHNOC H H H Ph 1-Et-Pn 1-645 2-EtSO_TwoHNOC H H H Ph cHx 1-646 2-EtSO_TwoHNOC H H H Ph -CH (Ph) Me 1-647 3-EtSO_TwoHNOC H H H Ph Bz 1-648 3-EtSO_TwoHNOC H H H Ph -CH (Ph) Me 1-649 4-EtSO_TwoHNOC H H H Ph 1-Et-Pn 1-650 4-EtSO_TwoHNOC H H H Ph cHx 1-651 4-EtSO_TwoHNOC H H H Ph -CH (Ph) Me 1-652 2-PrSO_TwoHNOC H H H Ph cHx 1-653 2-BuSO_TwoHNOC H H H Ph cHx 1-654 2- (2-Tol) SO_TwoHNOC H H H Ph 1-Et-Pn 1-655 2- (2-Tol) SO_TwoHNOC H H H Ph cHx 1-656 2- (2-Tol) SO_TwoHNOC H H H Ph -CH (Ph) Me 1-657 2- (3-Tol) SO_TwoHNOC H H H Ph 1-Et-Pn 1-658 2- (3-Tol) SO_TwoHNOC H H H Ph cHx 1-659 2- (3-Tol) SO_TwoHNOC H H H Ph -CH (Ph) Me 1-660 2- (4-Tol) SO_TwoHNOC H H H Ph 1-Et-Pn 1-661 2- (4-Tol) SO_TwoHNOC H H H Ph 2-Et-Hx 1-662 2- (4-Tol) SO_TwoHNOC H H H Ph cHx 1-663 2- (4-Tol) SO_TwoHNOC H H H Ph Bz 1-664 2- (4-Tol) SO_TwoHNOC H H H Ph -CH (Ph) Me 1-665 3- (2-Tol) SO_TwoHNOC H H H Ph 1-Et-Pn 1-666 3- (2-Tol) SO_TwoHNOC H H H Ph 2-Et-Hx 1-667 3- (2-Tol) SO_TwoHNOC H H H Ph cHx 1-668 3- (2-Tol) SO_TwoHNOC H H H Ph Bz 1-669 3- (2-Tol) SO_TwoHNOC H H H Ph -CH (Ph) Me 1-670 3- (3-Tol) SO_TwoHNOC H H H Ph 1-Et-Pn 1-671 3- (3-Tol) SO_TwoHNOC H H H Ph 2-Et-Hx 1-672 3- (3-Tol) SO_TwoHNOC H H H Ph cHx 1-673 3- (3-Tol) SO_TwoHNOC H H H Ph Bz 1-674 3- (3-Tol) SO_TwoHNOC H H H Ph -CH (Ph) Me 1-675 3- (4-Tol) SO_TwoHNOC H H H Ph iPr 1-676 3- (4-Tol) SO_TwoHNOC H H H Ph Bu 1-677 3- (4-Tol) SO_TwoHNOC H H H Ph tBu 1-678 3- (4-Tol) SO_TwoHNOC H H H Ph nPn 1-679 3- (4-Tol) SO_TwoHNOC H H H Ph 1-Et-Pn 1-680 3- (4-Tol) SO_TwoHNOC 4-Me H H Ph 1-Et-Pn 1-681 3- (4-Tol) SO_TwoHNOC 4-OMe H H Ph 1-Et-Pn 1-682 3- (4-Tol) SO_TwoHNOC 4-OMe 6-OH H Ph 1-Et-Pn 1-683 3- (4-Tol) SO_TwoHNOC 6-OMe H H Ph 1-Et-Pn 1-684 3- (4-Tol) SO_TwoHNOC 4-OH H H Ph 1-Et-Pn 1-685 3- (4-Tol) SO_TwoHNOC H H H Ph 2-Et-Hx 1-686 3- (4-Tol) SO_TwoHNOC H H H Ph cPn 1-687 3- (4-Tol) SO_TwoHNOC H H H Ph cHx 1-688 3- (4-Tol) SO_TwoHNOC H H H Ph 4-MeO-cHx 1-689 3- (4-Tol) SO_TwoHNOC H H H Ph 4-F-cHx 1-690 3- (4-Tol) SO_TwoHNOC H H H Ph 4-Cl-cHx 1-691 3- (4-Tol) SO_TwoHNOC H H H Ph 4-HO-cHx 1-692 3- (4-Tol) SO_TwoHNOC H H H Ph 4-Me-cHx 1-693 3- (4-Tol) SO_TwoHNOC H H H Ph 4-tBu-cHx 1-694 3- (4-Tol) SO_TwoHNOC H H H Ph Bz 1-695 3- (4-Tol) SO_TwoHNOC H H H Ph-(CH_Two)_Two-Ph 1-696 3- (4-Tol) SO_TwoHNOC H H H Ph -CH (Ph) Me 1-697 3- (4-Tol) SO_TwoHNOC 4-Me H H Ph -CH (Ph) Me 1-698 3- (4-Tol) SO_TwoHNOC 4-OMe H H Ph -CH (Ph) Me 1-699 3- (4-Tol) SO_TwoHNOC 4-OMe 6-OH H Ph -CH (Ph) Me 1-700 3- (4-Tol) SO_TwoHNOC 6-OMe H H Ph -CH (Ph) Me 1-701 3- (4-Tol) SO_TwoHNOC 4-OH H H Ph -CH (Ph) Me 1-702 3- (4-Tol) SO_TwoHNOC H H H Ph 1-Inda 1-703 3- (4-Tol) SO_TwoHNOC H H H Ph -CH (4-Br-Ph) Me 1-704 3- (4-Tol) SO_TwoHNOC H H H Ph -CH (1-Np) Me 1-705 4- (2-Tol) SO_TwoHNOC H H H Ph 1-Et-Pn 1-706 4- (2-Tol) SO_TwoHNOC H H H Ph cHx 1-707 4- (2-Tol) SO_TwoHNOC H H H Ph -CH (Ph) Me 1-708 4- (3-Tol) SO_TwoHNOC H H H Ph 1-Et-Pn 1-709 4- (3-Tol) SO_TwoHNOC H H H Ph cHx 1-710 4- (3-Tol) SO_TwoHNOC H H H Ph -CH (Ph) Me 1-711 4- (4-Tol) SO_TwoHNOC H H H Ph 1-Et-Pn 1-712 4- (4-Tol) SO_TwoHNOC H H H Ph 2-Et-Hx 1-713 4- (4-Tol) SO_TwoHNOC H H H Ph cHx 1-714 4- (4-Tol) SO_TwoHNOC H H H Ph Bz 1-715 4- (4-Tol) SO_TwoHNOC H H H Ph -CH (Ph) Me 1-716 2- (2-Et-Ph) SO_TwoHNOC H H H Ph cHx 1-717 2- (3-Et-Ph) SO_TwoHNOC H H H Ph cHx 1-718 2- (4-Et-Ph) SO_TwoHNOC H H H Ph 1-Et-Pn 1-719 2- (4-Et-Ph) SO_TwoHNOC H H H Ph cHx 1-720 2- (4-Et-Ph) SO_TwoHNOC H H H Ph -CH (Ph) Me 1-721 3- (2-Et-Ph) SO_TwoHNOC H H H Ph 1-Et-Pn 1-722 3- (2-Et-Ph) SO_TwoHNOC H H H Ph cHx 1-723 3- (2-Et-Ph) SO_TwoHNOC H H H Ph -CH (Ph) Me 1-724 3- (3-Et-Ph) SO_TwoHNOC H H H Ph 1-Et-Pn 1-725 3- (3-Et-Ph) SO_TwoHNOC H H H Ph cHx 1-726 3- (3-Et-Ph) SO_TwoHNOC H H H Ph -CH (Ph) Me 1-727 3- (4-Et-Ph) SO_TwoHNOC H H H Ph 1-Et-Pn 1-728 3- (4-Et-Ph) SO_TwoHNOC H H H Ph 2-Et-Hx 1-729 3- (4-Et-Ph) SO_TwoHNOC H H H Ph cHx 1-730 3- (4-Et-Ph) SO_TwoHNOC H H H Ph Bz 1-731 3- (4-Et-Ph) SO_TwoHNOC H H H Ph -CH (Ph) Me 1-732 3- (2-Et-Ph) SO_TwoHNOC H H H Ph cHx 1-733 3- (3-Et-Ph) SO_TwoHNOC H H H Ph cHx 1-734 3- (4-Et-Ph) SO_TwoHNOC H H H Ph 1-Et-Pn 1-735 3- (4-Et-Ph) SO_TwoHNOC H H H Ph cHx 1-736 3- (4-Et-Ph) SO_TwoHNOC H H H Ph -CH (Ph) Me 1-737 2- (4-Pr-Ph) SO_TwoHNOC H H H Ph cHx 1-738 3- (4-Pr-Ph) SO_TwoHNOC H H H Ph cHx 1-739 4- (2-Pr-Ph) SO_TwoHNOC H H H Ph cHx 1-740 4- (3-Pr-Ph) SO_TwoHNOC H H H Ph cHx 1-741 4- (4-Pr-Ph) SO_TwoHNOC H H H Ph 1-Et-Pn 1-742 4- (4-Pr-Ph) SO_TwoHNOC H H H Ph cHx 1-743 4- (4-Pr-Ph) SO_TwoHNOC H H H Ph -CH (Ph) Me 1-744 2- (4-MeO-Ph) SO_TwoHNOC H H H Ph cHx 1-745 3- (4-MeO-Ph) SO_TwoHNOC H H H Ph cHx 1-746 4- (2-MeO-Ph) SO_TwoHNOC H H H Ph cHx 1-747 4- (3-MeO-Ph) SO_TwoHNOC H H H Ph cHx 1-748 4- (4-MeO-Ph) SO_TwoHNOC H H H Ph 1-Et-Pn 1-749 4- (4-MeO-Ph) SO_TwoHNOC H H H Ph cHx 1-750 4- (4-MeO-Ph) SO_TwoHNOC H H H Ph -CH (Ph) Me 1-751 4- (4-EtO-Ph) SO_TwoHNOC H H H Ph cHx 1-752 2- (4-F-Ph) SO_TwoHNOC H H H Ph cHx 1-753 3- (4-F-Ph) SO_TwoHNOC H H H Ph cHx 1-754 4- (2-F-Ph) SO_TwoHNOC H H H Ph cHx 1-755 4- (3-F-Ph) SO_TwoHNOC H H H Ph cHx 1-756 4- (4-F-Ph) SO_TwoHNOC H H H Ph 1-Et-Pn 1-757 4- (4-F-Ph) SO_TwoHNOC H H H Ph cHx 1-758 4- (4-F-Ph) SO_TwoHNOC H H H Ph -CH (Ph) Me 1-759 2- (4-Cl-Ph) SO_TwoHNOC H H H Ph cHx 1-760 3- (4-Cl-Ph) SO_TwoHNOC H H H Ph cHx 1-761 4- (2-Cl-Ph) SO_TwoHNOC H H H Ph cHx 1-762 4- (3-Cl-Ph) SO_TwoHNOC H H H Ph cHx 1-763 4- (4-Cl-Ph) SO_TwoHNOC H H H Ph 1-Et-Pn 1-764 4- (4-Cl-Ph) SO_TwoHNOC H H H Ph cHx 1-765 4- (4-Cl-Ph) SO_TwoHNOC H H H Ph -CH (Ph) Me 1-766 2-PhSO_TwoHNOC H H H Ph cHx 1-767 3-PhSO_TwoHNOC H H H Ph cHx 1-768 3-PhSO_TwoHNOC H H H Ph 1-Et-Pn 1-769 3-PhSO_TwoHNOC H H H Ph -CH (Ph) Me 1-770 4-PhSO_TwoHNOC H H H Ph cHx 1-771 2- [2- (2-Tol) Ph] SO_TwoHNOC H H H Ph 1-Et-Pn 1-772 2- [2- (2-Tol) Ph] SO_TwoHNOC H H H Ph 2-Et-Hx 1-773 2- [2- (2-Tol) Ph] SO_TwoHNOC H H H Ph cHx 1-774 2- [2- (2-Tol) Ph] SO_TwoHNOC H H H Ph Bz 1-775 2- [2- (2-Tol) Ph] SO_TwoHNOC H H H Ph -CH (Ph) Me 1-776 2- [2- (3-Tol) Ph] SO_TwoHNOC H H H Ph 1-Et-Pn 1-777 2- [2- (3-Tol) Ph] SO_TwoHNOC H H H Ph cHx 1-778 2- [2- (3-Tol) Ph] SO_TwoHNOC H H H Ph -CH (Ph) Me 1-779 2- [2- (4-Tol) Ph] SO_TwoHNOC H H H Ph 1-Et-Pn 1-780 2- [2- (4-Tol) Ph] SO_TwoHNOC H H H Ph cHx 1-781 2- [2- (4-Tol) Ph] SO_TwoHNOC H H H Ph -CH (Ph) Me 1-782 3- [2- (2-Tol) Ph] SO_TwoHNOC H H H Ph iPr 1-783 3- [2- (2-Tol) Ph] SO_TwoHNOC H H H Ph Bu 1-784 3- [2- (2-Tol) Ph] SO_TwoHNOC H H H Ph tBu 1-785 3- [2- (2-Tol) Ph] SO_TwoHNOC H H H Ph nPn 1-786 3- [2- (2-Tol) Ph] SO_TwoHNOC H H H Ph 1-Et-Pn 1-787 3- [2- (2-Tol) Ph] SO_TwoHNOC H H H Ph 2-Et-Hx 1-788 3- [2- (2-Tol) Ph] SO_TwoHNOC H H H Ph cPn 1-789 3- [2- (2-Tol) Ph] SO_TwoHNOC H H H Ph cHx 1-790 3- [2- (2-Tol) Ph] SO_TwoHNOC H H H Ph 4-Me0-cHx 1-791 3- [2- (2-Tol) Ph] SO_TwoHNOC H H H Ph 4-F-cHx 1-792 3- [2- (2-Tol) Ph] SO_TwoHNOC H H H Ph 4-Cl-cHx 1-793 3- [2- (2-Tol) Ph] SO_TwoHNOC H H H Ph 4-HO-cHx 1-794 3- [2- (2-Tol) Ph] SO_TwoHNOC H H H Ph 4-HOH_TwoC-cHx 1-795 3- [2- (2-Tol) Ph] SO_TwoHNOC H H H Ph -CH_Two-(4-HOH_TwoC-cHx) 1-796 3- [2- (2-Tol) Ph] SO_TwoHNOC H H H Ph -CH_Two-(4-HOOC-cHx) 1-797 3- [2- (2-Tol) Ph] SO_TwoHNOC H H H Ph -CH_Two-[4- (Me)_TwoNOC-cHx] 1-798 3- [2- (2-Tol) Ph] SO_TwoHNOC H H H Ph 4-Me-cHx 1-799 3- [2- (2-Tol) Ph] SO_TwoHNOC H H H Ph 4-tBu-cHx 1-800 3- [2- (2-Tol) Ph] SO_TwoHNOC H H H Ph Bz 1-801 3- [2- (2-Tol) Ph] SO_TwoHNOC H H H Ph-(CH_Two)_Two-Ph 1-802 3- [2- (2-Tol) Ph] SO_TwoHNOC H H H Ph -CH (Ph) Me 1-803 3- [2- (2-Tol) Ph] SO_TwoHNOC 4-Me H H Ph -CH (Ph) Me 1-804 3- [2- (2-Tol) Ph] SO_TwoHNOC 4-OMe H H Ph -CH (Ph) Me 1-805 3- [2- (2-Tol) Ph] SO_TwoHNOC 4-OMe 6-OH H Ph -CH (Ph) Me 1-806 3- [2- (2-Tol) Ph] SO_TwoHNOC 6-OMe H H Ph -CH (Ph) Me 1-807 3- [2- (2-Tol) Ph] SO_TwoHNOC 4-OH H H Ph -CH (Ph) Me 1-808 3- [2- (2-Tol) Ph] SO_TwoHNOC H H H Ph 1-Inda 1-809 3- [2- (2-Tol) Ph] SO_TwoHNOC H H H Ph -CH (4-Br-Ph) Me 1-810 3- [2- (2-Tol) Ph] SO_TwoHNOC H H H Ph -CH (1-Np) Me 1-811 3- [2- (3-Tol) Ph] SO_TwoHNOC H H H Ph 1-Et-Pn 1-812 3- [2- (3-Tol) Ph] SO_TwoHNOC H H H Ph 2-Et-Hx 1-813 3- [2- (3-Tol) Ph] SO_TwoHNOC H H H Ph cHx 1-814 3- [2- (3-Tol) Ph] SO_TwoHNOC H H H Ph Bz 1-816 3- [2- (4-Tol) Ph] SO_TwoHNOC H H H Ph 1-Et-Pn 1-817 3- [2- (4-Tol) Ph] SO_TwoHNOC H H H Ph 2-Et-Hx 1-818 3- [2- (4-Tol) Ph] SO_TwoHNOC H H H Ph cHx 1-819 3- [2- (4-Tol) Ph] SO_TwoHNOC H H H Ph Bz 1-820 3- [2- (4-Tol) Ph] SO_TwoHNOC H H H Ph -CH (Ph) Me 1-821 3- [3- (2-Tol) Ph] SO_TwoHNOC H H H Ph 1-Et-Pn 1-822 3- [3- (2-Tol) Ph] SO_TwoHNOC H H H Ph 2-Et-Hx 1-823 3- [3- (2-Tol) Ph] SO_TwoHNOC H H H Ph cHx 1-824 3- [3- (2-Tol) Ph] SO_TwoHNOC H H H Ph Bz 1-825 3- [3- (2-Tol) Ph] SO_TwoHNOC H H H Ph -CH (Ph) Me 1-826 3- [3- (3-Tol) Ph] SO_TwoHNOC H H H Ph 1-Et-Pn 1-827 3- [3- (3-Tol) Ph] SO_TwoHNOC H H H Ph cHx 1-828 3- [3- (3-Tol) Ph] SO_TwoHNOC H H H Ph -CH (Ph) Me 1-829 3- [3- (4-Tol) Ph] SO_TwoHNOC H H H Ph 1-Et-Pn 1-830 3- [3- (4-Tol) Ph] SO_TwoHNOC H H H Ph cHx 1-831 3- [3- (4-Tol) Ph] SO_TwoHNOC H H H Ph -CH (Ph) Me 1-832 3- [4- (2-Tol) Ph] SO_TwoHNOC H H H Ph 1-Et-Pn 1-833 3- [4- (2-Tol) Ph] SO_TwoHNOC H H H Ph 2-Et-Hx 1-834 3- [4- (2-Tol) Ph] SO_TwoHNOC H H H Ph cHx 1-835 3- [4- (2-Tol) Ph] SO_TwoHNOC H H H Ph Bz 1-836 3- [4- (2-Tol) Ph] SO_TwoHNOC H H H Ph -CH (Ph) Me 1-837 3- [4- (3-Tol) Ph] SO_TwoHNOC H H H Ph 1-Et-Pn 1-838 3- [4- (3-Tol) Ph] SO_TwoHNOC H H H Ph cHx 1-839 3- [4- (3-Tol) Ph] SO_TwoHNOC H H H Ph -CH (Ph) Me 1-840 3- [4- (4-Tol) Ph] SO_TwoHNOC H H H Ph 1-Et-Pn 1-841 3- [4- (4-Tol) Ph] SO_TwoHNOC H H H Ph cHx 1-842 3- [4- (4-Tol) Ph] SO_TwoHNOC H H H Ph -CH (Ph) Me 1-843 4- [2- (2-Tol) Ph] SO_TwoHNOC H H H Ph 1-Et-Pn 1-845 4- [2- (2-Tol) Ph] SO_TwoHNOC H H H Ph cHx 1-846 4- [2- (2-Tol) Ph] SO_TwoHNOC H H H Ph Bz 1-847 4- [2- (2-Tol) Ph] SO_TwoHNOC H H H Ph -CH (Ph) Me 1-848 4- [2- (3-Tol) Ph] SO_TwoHNOC H H H Ph 1-Et-Pn 1-849 4- [2- (3-Tol) Ph] SO_TwoHNOC H H H Ph cHx 1-850 4- [2- (3-Tol) Ph] SO_TwoHNOC H H H Ph -CH (Ph) Me 1-851 4- [2- (4-Tol) Ph] SO_TwoHNOC H H H Ph 1-Et-Pn 1-852 4- [2- (4-Tol) Ph] SO_TwoHNOC H H H Ph cHx 1-853 4- [2- (4-Tol) Ph] SO_TwoHNOC H H H Ph -CH (Ph) Me 1-854 4- [2- (2-Et-Ph) Ph] SO_TwoHNOC H H H Ph 1-Et-Pn 1-855 4- [2- (2-Et-Ph) Ph] SO_TwoHNOC H H H Ph cHx 1-856 4- [2- (2-Et-Ph) Ph] SO_TwoHNOC H H H Ph -CH (Ph) Me 1-857 4- [2- (3-Et-Ph) Ph] SO_TwoHNOC H H H Ph -CH (Ph) Me 1-858 4- [2- (4-Et-Ph) Ph] SO_TwoHNOC H H H Ph -CH (Ph) Me 1-859 4- [2- (4-Et-Ph) Ph] SO_TwoHNOC H H H Ph -CH (Ph) Me 1-860 4- [2- (2-MeO-Ph) Ph] SO_TwoHNOC H H H Ph 1-Et-Pn 1-861 4- [2- (2-MeO-Ph) Ph] SO_TwoHNOC H H H Ph cHx 1-862 4- [2- (2-MeO-Ph) Ph] SO_TwoHNOC H H H Ph -CH (Ph) Me 1-863 4- [2- (2-MeO-Ph) Ph] SO_TwoHNOC H H H Ph-CH (Ph) Me 1-864 4- [2- (2-MeO-Ph) Ph] SO₂HNOC H H H Ph -CH (Ph) Me 1-865 4- [2- (2-F-Ph) Ph] SO_TwoHNOC H H H Ph 1-Et-Pn 1-866 4- [2- (2-F-Ph) Ph] SO_TwoHNOC H H H Ph cHx 1-867 4- [2- (2-F-Ph) Ph] SO_TwoHNOC H H H Ph -CH (Ph) Me 1-868 4- [2- (3-F-Ph) Ph] SO_TwoHNOC H H H Ph -CH (Ph) Me 1-869 4- [2- (4-F-Ph) Ph] SO_TwoHNOC H H H Ph -CH (Ph) Me 1-870 2-HO_ThreeS H H H Ph 1-Et-Pn 1-871 2-HO_ThreeS H H H Ph cHx 1-872 2-HO_ThreeS H H H Ph -CH (Ph) Me 1-873 3-HO_ThreeS H H H Ph 1-Et-Pn 1-874 3-HO_ThreeS H H H Ph cHx 1-875 3-HO_ThreeS H H H Ph -CH (Ph) Me 1-876 4-HO_ThreeS H H H Ph 1-Et-Pn 1-877 4-HO_ThreeS H H H Ph cHx 1-878 4-HO_ThreeS H H H Ph -CH (Ph) Me 1-879 2-MeSO_Two H H H Ph iPr 1-880 2-MeSO_Two H H H Ph Bu 1-881 2-MeSO_Two H H H Ph tBu 1-882 2-MeSO_Two H H H Ph nPn 1-883 2-MeSO_Two H H H Ph 2-Hx 1-884 2-MeSO_Two H H H Ph 1-Et-Pn 1-885 2-MeSO_Two 4-Me H H Ph 1-Et-Pn 1-886 2-MeSO_Two 4-OMe H H Ph 1-Et-Pn 1-887 2-MeSO_Two 4-OMe 6-OH H Ph 1-Et-Pn 1-888 2-MeSO_Two 4-OMe 5-F 6-OH Ph 1-Et-Pn 1-889 2-MeSO_Two 6-OMe H H Ph 1-Et-Pn 1-890 2-MeSO_Two 4-OH H H Ph 1-Et-Pn 1-891 2-MeSO_Two 4-F H H Ph 1-Et-Pn 1-892 2-MeSO_Two 4-Cl H H Ph 1-Et-Pn 1-893 2-MeSO_Two 4-NH_Two H H Ph 1-Et-Pn 1-894 2-MeSO_Two 4-NHMe H H Ph 1-Et-Pn 1-895 2-MeSO_Two 4-N (Me)_Two H H Ph 1-Et-Pn 1-896 2-MeSO_Two H H H 2-Me-Ph 1-Et-Pn 1-897 2-MeSO_Two H H H 3-Me-Ph 1-Et-Pn 1-898 2-MeSO_Two H H H 4-Me-Ph 1-Et-Pn 1-899 2-MeSO_Two H H H 4-MeO-Ph 1-Et-Pn 1-900 2-MeSO_Two H H H 4-F-Ph 1-Et-Pn 1-901 2-MeSO_Two H H H 4-Cl-Ph 1-Et-Pn 1-902 2-MeSO_Two H H H 1-Et-Pn R^5a= 4-Me-2-MeO-Ph 1-903 2-MeSO_Two H H H 1-Et-Pn R^5a= 6-F-4-Me-2-MeO-Ph 1-904 2-MeSO_Two H H H Ph 2-Et-Hx 1-905 2-MeSO_Two H H H Ph cPn 1-906 2-MeSO_Two H H H Ph cHx 1-907 2-MeSO_Two 4-Me H H Ph cHx 1-908 2-MeSO_Two 4-OMe H H Ph cHx 1-909 2-MeSO_Two 4-OMe 6-OH H Ph cHx 1-910 2-MeSO_Two 6-OMe H H Ph cHx 1-911 2-MeSO_Two H H H 2-Me-Ph cHx 1-912 2-MeSO_Two H H H 3-Me-Ph cHx 1-913 2-MeSO_Two H H H 4-Me-Ph cHx 1-914 2-MeSO_Two H H H 4-MeO-Ph cHx 1-915 2-MeSO_Two H H H 4-F-Ph cHx 1-916 2-MeSO_Two H H H 4-Cl-Ph cHx 1-917 2-MeSO_Two H H H Ph 4-Me-cHx 1-918 2-MeSO_Two H H H Ph 4-tBu-cHx 1-919 2-MeSO_Two H H H Ph 4-Me0-cHx 1-920 2-MeSO_Two H H H Ph 4-F-cHx 1-921 2-MeSO_Two H H H Ph 4-Cl-cHx 1-922 2-MeSO_Two H H H Ph 4-HO-cHx 1-923 2-MeSO_Two H H H Ph 4-HOH_TwoC-cHx 1-924 2-MeSO_Two H H H Ph -CH_Two-(4-HOH_TwoC-cHx) 1-925 2-MeSO_Two H H H Ph -CH_Two-(4-HOOC-cHx) 1-926 2-MeSO_Two H H H Ph -CH_Two-[4- (Me)_TwoNOC-cHx] 1-927 2-MeSO_Two H H H Ph 1-Inda 1-928 2-MeSO_Two H H H Ph Bz 1-929 2-MeSO_Two H H H Ph 4-Me-Bz 1-930 2-MeSO_Two H H H Ph-(CH_Two)_Two-Ph 1-931 2-MeSO_Two H H H Ph -CH (Ph) Me 1-932 2-MeSO_Two 4-Me H H Ph -CH (Ph) Me 1-933 2-MeSO_Two 4-OMe H H Ph -CH (Ph) Me 1-934 2-MeSO_Two 4-OMe 6-OH H Ph -CH (Ph) Me 1-935 2-MeSO_Two 4-OMe 5-F 6-OH Ph -CH (Ph) Me 1-936 2-MeSO_Two 6-OMe H H Ph -CH (Ph) Me 1-937 2-MeSO_Two 4-OH H H Ph -CH (Ph) Me 1-938 2-MeSO_Two 4-F H H Ph -CH (Ph) Me 1-939 2-MeSO_Two 4-Cl H H Ph -CH (Ph) Me 1-940 2-MeSO_Two 4-NH_Two H H Ph -CH (Ph) Me 1-941 2-MeSO_Two 4-NHMe H H Ph -CH (Ph) Me 1-942 2-MeSO_Two 4-N (Me)_Two H H Ph -CH (Ph) Me 1-943 2-MeSO_Two H H H 2-Me-Ph -CH (Ph) Me 1-944 2-MeSO_Two H H H 3-Me-Ph -CH (Ph) Me 1-945 2-MeSO_Two H H H 4-Me-Ph -CH (Ph) Me 1-946 2-MeSO_Two H H H 4-MeO-Ph -CH (Ph) Me 1-947 2-MeSO_Two H H H 4-F -Ph -CH (Ph) Me 1-948 2-MeSO_Two H H H 4-Cl-Ph -CH (Ph) Me 1-949 2-MeSO_Two H H H -CH (Ph) Me R^5a= 4-Me-2-MeO-Ph 1-950 2-MeSO_Two H H H -CH (Ph) Me R^5a= 6-F-4-Me-2-MeO-Ph 1-951 2-MeSO_Two H H H Ph -CH (4-Me-Ph) Me 1-952 2-MeSO_Two H H H Ph -CH (4-MeO-Ph) Me 1-953 2-MeSO_Two H H H Ph -CH (4-F-Ph) Me 1-954 2-MeSO_Two H H H Ph -CH (4-Cl-Ph) Me 1-955 2-MeSO_Two H H H Ph 3-Pn 1-956 2-MeSO_Two H H H 4-Me-Ph 3-Pn 1-957 2-MeSO_Two H H H Ph -CH (cHx) Me 1-958 2-MeSO_Two H H H 4-Me-Ph -CH (cHx) Me 1-959 2-MeSO_Two H H H Ph -CH (4-Br-Ph) Me 1-960 2-MeSO_Two H H H 4-Me-Ph -CH (4-Br-Ph) Me 1-961 2-MeSO_Two 4-Me H H Ph -CH (4-Br-Ph) Me 1-962 2-MeSO_Two 4-F H H Ph -CH (4-Br-Ph) Me 1-963 2-MeSO_Two H H H Ph -CH_Two(4-H_TwoNOC-Ph) 1-964 2-MeSO_Two H H H 4-Me-Ph -CH_Two(4-H_TwoNOC-Ph) 1-965 2-MeSO_Two H H H Ph -CH (1-Np) Me 1-966 2-MeSO_Two H H H 4-Me-Ph -CH (1-Np) Me 1-967 3-MeSO_Two H H H Ph iPr 1-968 3-MeSO_Two H H H Ph Bu 1-969 3-MeSO_Two H H H Ph tBu 1-970 3-MeSO_Two H H H Ph nPn 1-971 3-MeSO_Two H H H Ph 2-Hx 1-972 3-MeSO_Two H H H Ph 1-Et-Pn 1-973 3-MeSO_Two 4-Me H H Ph 1-Et-Pn 1-974 3-MeSO_Two 4-OMe H H Ph 1-Et-Pn 1-975 3-MeSO_Two 4-OMe 6-OH H Ph 1-Et-Pn 1-976 3-MeSO_Two 4-OMe 5-F 6-OH Ph 1-Et-Pn 1-977 3-MeSO_Two 6-OMe H H Ph 1-Et-Pn 1-978 3-MeSO_Two 4-OH H H Ph 1-Et-Pn 1-979 3-MeSO_Two 4-F H H Ph 1-Et-Pn 1-980 3-MeSO_Two 4-Cl H H Ph 1-Et-Pn 1-981 3-MeSO_Two 4-NH_Two H H Ph 1-Et-Pn 1-982 3-MeSO_Two 4-NHMe H H Ph 1-Et-Pn 1-983 3-MeSO_Two 4-N (Me)_Two H H Ph 1-Et-Pn 1-984 3-MeSO_Two H H H 2-Me-Ph 1-Et-Pn 1-985 3-MeSO_Two H H H 3-Me-Ph 1-Et-Pn 1-986 3-MeSO_Two H H H 4-Me-Ph 1-Et-Pn 1-987 3-MeSO_Two H H H 4-MeO-Ph 1-Et-Pn 1-988 3-MeSO_Two H H H 4-F -Ph 1-Et-Pn 1-989 3-MeSO_Two H H H 4-Cl-Ph 1-Et-Pn 1-990 3-MeSO_Two H H H 1-Et-Pn R^5a= 4-Me-2-MeO-Ph 1-991 3-MeSO_Two H H H 1-Et-Pn R^5a= 6-F-4-Me-2-MeO-Ph 1-992 3-MeSO_Two H H H Ph 2-Et-Hx 1-993 3-MeSO_Two H H H Ph cPn 1-994 3-MeSO_Two H H H Ph cHx 1-995 3-MeSO_Two 4-Me H H Ph cHx 1-996 3-MeSO_Two 4-OMe H H Ph cHx 1-997 3-MeSO_Two 4-OMe 6-OH H Ph cHx 1-998 3-MeSO_Two 6-OMe H H Ph cHx 1-999 3-MeSO_Two 4-OH H H Ph cHx 1-1000 3-MeSO_Two H H H Ph 4-Me-cHx 1-1001 3-MeSO_Two H H H Ph 4-tBu-cHx 1-1002 3-MeSO_Two H H H Ph 4-Me0-cHx 1-1003 3-MeSO_Two H H H Ph 4-F-cHx 1-1004 3-MeSO_Two H H H Ph 4-Cl-cHx 1-1005 3-MeSO_Two H H H Ph 4-HO-cHx 1-1006 3-MeSO_Two H H H Ph 4-HOH_TwoC-cHx 1-1007 3-MeSO_Two H H H Ph -CH_Two-(4-HOH_TwoC-cHx) 1-1008 3-MeSO_Two H H H Ph -CH_Two-(4-HOOC-cHx) 1-1009 3-MeSO_Two H H H Ph -CH_Two-[4- (Me)_TwoNOC-cHx] 1-1010 3-MeSO_Two H H H Ph 1-Inda 1-1011 3-MeSO_Two H H H Ph Bz 1-1012 3-MeSO_Two H H H Ph 4-Me-Bz 1-1013 3-MeSO_Two H H H Ph-(CH_Two)_Two-Ph 1-1014 3-MeSO_Two H H H Ph -CH (Ph) Me 1-1015 3-MeSO_Two 4-Me H H Ph -CH (Ph) Me 1-1016 3-MeSO_Two 4-OMe H H Ph -CH (Ph) Me 1-1017 3-MeSO_Two 4-OMe 6-OH H Ph -CH (Ph) Me 1-1018 3-MeSO_Two 4-OMe 5-F 6-OH Ph -CH (Ph) Me 1-1019 3-MeSO_Two 6-OMe H H Ph -CH (Ph) Me 1-1020 3-MeSO_Two 4-OH H H Ph -CH (Ph) Me 1-1021 3-MeSO_Two 4-F H H Ph -CH (Ph) Me 1-1022 3-MeSO_Two 4-Cl H H Ph -CH (Ph) Me 1-1023 3-MeSO_Two 4-NH_Two H H Ph -CH (Ph) Me 1-1024 3-MeSO_Two 4-NHMe H H Ph -CH (Ph) Me 1-1025 3-MeSO_Two 4-N (Me)_Two H H Ph -CH (Ph) Me 1-1026 3-MeSO_Two H H H 2-Me-Ph -CH (Ph) Me 1-1027 3-MeSO_Two H H H 3-Me-Ph -CH (Ph) Me 1-1028 3-MeSO_Two H H H 4-Me-Ph -CH (Ph) Me 1-1029 3-MeSO_Two H H H 4-MeO-Ph -CH (Ph) Me 1-1030 3-MeSO_Two H H H 4-F -Ph -CH (Ph) Me 1-1031 3-MeSO_Two H H H 4-Cl-Ph -CH (Ph) Me 1-1032 3-MeSO_Two H H H -CH (Ph) Me R^5a= 4-Me-2-MeO-Ph 1-1033 3-MeSO_Two H H H -CH (Ph) Me R^5a= 6-F-4-Me-2-MeO-Ph 1-1034 3-MeSO_Two H H H Ph -CH (4-Me-Ph) Me 1-1035 3-MeSO_Two H H H Ph -CH (4-MeO-Ph) Me 1-1036 3-MeSO_Two H H H Ph -CH (4-F-Ph) Me 1-1037 3-MeSO_Two H H H Ph -CH (4-Cl-Ph) Me 1-1038 3-MeSO_Two H H H Ph 3-Pn 1-1039 3-MeSO_Two H H H 4-Me-Ph 3-Pn 1-1040 3-MeSO_Two H H H Ph -CH (cHx) Me 1-1041 3-MeSO_Two H H H 4-Me-Ph -CH (cHx) Me 1-1042 3-MeSO_Two H H H Ph -CH (4-Br-Ph) Me 1-1043 3-MeSO_Two H H H 4-Me-Ph -CH (4-Br-Ph) Me 1-1044 3-MeSO_Two 4-Me H H Ph -CH (4-Br-Ph) Me 1-1045 3-MeSO_Two 4-F H H Ph -CH (4-Br-Ph) Me 1-1046 3-MeSO_Two H H H Ph -CH_Two(4-H_TwoNOC-Ph) 1-1047 3-MeSO_Two H H H 4-Me-Ph -CH_Two(4-H_TwoNOC-Ph) 1-1048 3-MeSO_Two H H H Ph -CH (1-Np) Me 1-1049 3-MeSO_Two H H H 4-Me-Ph -CH (1-Np) Me 1-1050 4-MeSO_Two H H H Ph iPr 1-1051 4-MeSO_Two H H H Ph Bu 1-1052 4-MeSO_Two H H H Ph tBu 1-1053 4-MeSO_Two H H H Ph nPn 1-1054 4-MeSO_Two H H H Ph 2-Hx 1-1055 4-MeSO_Two H H H Ph 1-Et-Pn 1-1056 4-MeSO_Two 2-Me H H Ph 1-Et-Pn 1-1058 4-MeSO_Two 2-OMe 6-OH H Ph 1-Et-Pn 1-1059 4-MeSO_Two 2-OMe 5-F 6-OH Ph 1-Et-Pn 1-1060 4-MeSO_Two 6-OMe H H Ph 1-Et-Pn 1-1061 4-MeSO_Two 2-OH H H Ph 1-Et-Pn 1-1062 4-MeSO_Two 2-F H H Ph 1-Et-Pn 1-1063 4-MeSO_Two 2-Cl H H Ph 1-Et-Pn 1-1064 4-MeSO_Two 2-NH_Two H H Ph 1-Et-Pn 1-1065 4-MeSO_Two 2-NHMe H H Ph 1-Et-Pn 1-1066 4-MeSO_Two 2-N (Me)_Two H H Ph 1-Et-Pn 1-1067 4-MeSO_Two H H H 2-Me-Ph 1-Et-Pn 1-1068 4-MeSO_Two H H H 3-Me-Ph 1-Et-Pn 1-1069 4-MeSO_Two H H H 4-Me-Ph 1-Et-Pn 1-1070 4-MeSO_Two H H H 4-MeO-Ph 1-Et-Pn 1-1071 4-MeSO_Two H H H 4-F -Ph 1-Et-Pn 1-1072 4-MeSO_Two H H H 4-Cl-Ph 1-Et-Pn 1-1073 4-MeSO_Two H H H 1-Et-Pn R^5a= 4-Me-2-MeO-Ph 1-1074 4-MeSO_Two H H H 1-Et-Pn R^5a= 6-F-4-Me-2-MeO-Ph 1-1075 4-MeSO_Two H H H Ph 2-Et-Hx 1-1076 4-MeSO_Two H H H Ph cPn 1-1077 4-MeSO_Two H H H Ph cHx 1-1078 4-MeSO_Two 2-Me H H Ph cHx 1-1079 4-MeSO_Two 2-OMe H H Ph cHx 1-1080 4-MeSO_Two 2-OMe 6-OH H Ph cHx 1-1081 4-MeSO_Two 6-OMe H H Ph cHx 1-1082 4-MeSO_Two 2-OH H H Ph cHx 1-1083 4-MeSO_Two H H H Ph 4-Me-cHx 1-1084 4-MeSO_Two H H H Ph 4-tBu-cHx 1-1085 4-MeSO_Two H H H Ph 4-MeO-cHx 1-1086 4-MeSO_Two H H H Ph 4-F-cHx 1-1087 4-MeSO_Two H H H Ph 4-Cl-cHx 1-1088 4-MeSO_Two H H H Ph 4-HO-cHx 1-1089 4-MeSO_Two H H H Ph 4-HOH_TwoC-cHx 1-1090 4-MeSO_Two H H H Ph -CH_Two-(4-HOH_TwoC-cHx) 1-1091 4-MeSO_Two H H H Ph -CH_Two-(4-HOOC-cHx) 1-1092 4-MeSO_Two H H H Ph -CH_Two-[4- (Me)_TwoNOC-cHx] 1-1093 4-MeSO_Two H H H Ph 1-Inda 1-1094 4-MeSO_Two H H H Ph Bz 1-1095 4-MeSO_Two H H H Ph 4-Me-Bz 1-1096 4-MeSO_Two H H H Ph-(CH_Two)_Two-Ph 1-1097 4-MeSO_Two H H H Ph -CH (Ph) Me 1-1098 4-MeSO_Two 2-Me H H Ph -CH (Ph) Me 1-1099 4-MeSO_Two 2-OMe H H Ph -CH (Ph) Me 1-1100 4-MeSO_Two 2-OMe 6-OH H Ph -CH (Ph) Me 1-1101 4-MeSO_Two 2-OMe 5-F 6-OH Ph -CH (Ph) Me 1-1102 4-MeSO_Two 6-OMe H H Ph -CH (Ph) Me 1-1103 4-MeSO_Two 2-OH H H Ph -CH (Ph) Me 1-1104 4-MeSO_Two 2-F H H Ph -CH (Ph) Me 1-1105 4-MeSO_Two 2-Cl H H Ph -CH (Ph) Me 1-1106 4-MeSO_Two 2-NH_Two H H Ph -CH (Ph) Me 1-1107 4-MeSO_Two 2-NHMe H H Ph -CH (Ph) Me 1-1108 4-MeSO_Two 2-N (Me)_Two H H Ph -CH (Ph) Me 1-1109 4-MeSO_Two H H H 2-Me-Ph -CH (Ph) Me 1-1110 4-MeSO_Two H H H 3-Me-Ph -CH (Ph) Me 1-1111 4-MeSO_Two H H H 4-Me-Ph -CH (Ph) Me 1-1112 4-MeSO_Two H H H 4-MeO-Ph -CH (Ph) Me 1-1113 4-MeSO_Two H H H 4-F-Ph -CH (Ph) Me 1-1114 4-MeSO_Two H H H 4-Cl-Ph -CH (Ph) Me 1-1115 4-MeSO_Two H H H -CH (Ph) Me R^5a= 4-Me-2-MeO-Ph 1-1116 4-MeSO_Two H H H -CH (Ph) Me R^5a= 6-F-4-Me-2-MeO-Ph 1-1117 4-MeSO_Two H H H Ph -CH (4-Me-Ph) Me 1-1118 4-MeSO_Two H H H Ph -CH (4-MeO-Ph) Me 1-1119 4-MeSO_Two H H H Ph -CH (4-F-Ph) Me 1-1120 4-MeSO_Two H H H Ph -CH (4-Cl-Ph) Me 1-1121 4-MeSO_Two H H H Ph 3-Pn 1-1122 4-MeSO_Two H H H 4-Me-Ph 3-Pn 1-1123 4-MeSO_Two H H H Ph -CH (cHx) Me 1-1124 4-MeSO_Two H H H 4-Me-Ph -CH (cHx) Me 1-1125 4-MeSO_Two H H H Ph -CH (4-Br-Ph) Me 1-1126 4-MeSO_Two H H H 4-Me-Ph -CH (4-Br-Ph) Me 1-1127 4-MeSO_Two 2-Me H H Ph -CH (4-Br-Ph) Me 1-1128 4-MeSO_Two 2-F H H Ph -CH (4-Br-Ph) Me 1-1129 4-MeSO_Two H H H Ph -CH_Two(4-H_TwoNOC-Ph) 1-1130 4-MeSO_Two H H H 4-Me-Ph -CH_Two(4-H_TwoNOC-Ph) 1-1131 4-MeSO_Two H H H Ph -CH (1-Np) Me 1-1132 4-MeSO_Two H H H 4-Me-Ph -CH (1-Np) Me 1-1133 2-EtSO_Two H H H Ph iPr 1-1134 2-EtSO_Two H H H Ph Bu 1-1135 2-EtSO_Two H H H Ph tBu 1-1136 2-EtSO_Two H H H Ph nPn 1-1137 2-EtSO_Two H H H Ph 2-Hex 1-1138 2-EtSO_Two H H H Ph 1-Et-Pn 1-1139 2-EtSO_Two 4-Me H H Ph 1-Et-Pn 1-1140 2-EtSO_Two 4-OMe H H Ph 1-Et-Pn 1-1141 2-EtSO_Two 4-OMe 6-OH H Ph 1-Et-Pn 1-1142 2-EtSO_Two 4-OMe 5-F 6-OH Ph 1-Et-Pn 1-1143 2-EtSO_Two 6-OMe H H Ph 1-Et-Pn 1-1144 2-EtSO_Two 4-OH H H Ph 1-Et-Pn 1-1145 2-EtSO_Two 4-F H H Ph 1-Et-Pn 1-1146 2-EtSO_Two 4-Cl H H Ph 1-Et-Pn 1-1147 2-EtSO_Two 4-NH_Two H H Ph 1-Et-Pn 1-1148 2-EtSO_Two 4-NHMe H H Ph 1-Et-Pn 1-1149 2-EtSO_Two 4-N (Me)_Two H H Ph 1-Et-Pn 1-1150 2-EtSO_Two H H H 2-Me-Ph 1-Et-Pn 1-1151 2-EtSO_Two H H H 3-Me-Ph 1-Et-Pn 1-1152 2-EtSO_Two H H H 4-Me-Ph 1-Et-Pn 1-1153 2-EtSO_Two H H H 4-MeO-Ph 1-Et-Pn 1-1154 2-EtSO_Two H H H 4-F -Ph 1-Et-Pn 1-1155 2-EtSO_Two H H H 4-Cl-Ph 1-Et-Pn 1-1156 2-EtSO_Two H H H 1-Et-Pn R^5a= 4-Me-2-MeO-Ph 1-1157 2-EtSO_Two H H H 1-Et-Pn R^5a= 6-F-4-Me-2-MeO-Ph 1-1158 2-EtSO_Two H H H Ph 2-Et-Hx 1-1159 2-EtSO_Two H H H Ph cPn 1-1160 2-EtSO_Two H H H Ph cHx 1-1161 2-EtSO_Two 4-Me H H Ph cHx 1-1162 2-EtSO_Two 4-OMe H H Ph cHx 1-1163 2-EtSO_Two 4-OMe 6-OH H Ph cHx 1-1164 2-EtSO_Two 6-OMe H H Ph cHx 1-1165 2-EtSO_Two 4-OH H H Ph cHx 1-1166 2-EtSO_Two H H H Ph 4-Me-cHx 1-1167 2-EtSO_Two H H H Ph 4-tBu-cHx 1-1168 2-EtSO_Two H H H Ph 4-MeO-cHx 1-1169 2-EtSO_Two H H H Ph 4-F-cHx 1-1170 2-EtSO_Two H H H Ph 4-Cl-cHx 1-1171 2-EtSO_Two H H H Ph 4-HO-cHx 1-1172 2-EtSO_Two H H H Ph 4-HOH_TwoC-cHx 1-1173 2-EtSO_Two H H H Ph -CH_Two-(4-HOH_TwoC-cHx) 1-1174 2-EtSO_Two H H H Ph -CH_Two-(4-HOOC-cHx) 1-1175 2-EtSO_Two H H H Ph -CH_Two-(4-MeOOC-cHx) 1-1176 2-EtSO_Two H H H Ph -CH_Two-[4- (Me)_TwoNOC-cHx] 1-1177 2-EtSO_Two H H H Ph 1-Inda 1-1178 2-EtSO_Two H H H Ph Bz 1-1179 2-EtSO_Two H H H Ph 4-Me-Bz 1-1180 2-EtSO_Two H H H Ph-(CH_Two)_Two-Ph 1-1181 2-EtSO_Two H H H Ph -CH (Ph) Me 1-1182 2-EtSO_Two 4-Me H H Ph -CH (Ph) Me 1-1183 2-EtSO_Two 4-OMe H H Ph -CH (Ph) Me 1-1184 2-EtSO_Two 4-OMe 6-OH H Ph -CH (Ph) Me 1-1185 2-EtSO_Two 4-OMe 5-F 6-OH Ph -CH (Ph) Me 1-1186 2-EtSO_Two 6-OMe H H Ph -CH (Ph) Me 1-1187 2-EtSO_Two 4-OH H H Ph -CH (Ph) Me 1-1188 2-EtSO_Two 4-F H H Ph -CH (Ph) Me 1-1189 2-EtSO_Two 4-Cl H H Ph -CH (Ph) Me 1-1190 2-EtSO_Two 4-NH_Two H H Ph -CH (Ph) Me 1-1191 2-EtSO_Two 4-NHMe H H Ph -CH (Ph) Me 1-1192 2-EtSO_Two 4-N (Me)_Two H H Ph -CH (Ph) Me 1-1193 2-EtSO_Two H H H 2-Me-Ph -CH (Ph) Me 1-1194 2-EtSO_Two H H H 3-Me-Ph -CH (Ph) Me 1-1195 2-EtSO_Two H H H 4-Me-Ph -CH (Ph) Me 1-1196 2-EtSO_Two H H H 4-MeO-Ph -CH (Ph) Me 1-1197 2-EtSO_Two H H H 4-F -Ph -CH (Ph) Me 1-1198 2-EtSO_Two H H H 4-Cl-Ph -CH (Ph) Me 1-1199 2-EtSO_Two H H H -CH (Ph) Me R^5a= 4-Me-2-MeO-Ph 1-1200 2-EtSO_Two H H H -CH (Ph) Me R^5a= 6-F-4-Me-2-MeO-Ph 1-1201 2-EtSO_Two H H H Ph -CH (4-Me-Ph) Me 1-1202 2-EtSO_Two H H H Ph -CH (4-MeO-Ph) Me 1-1203 2-EtSO_Two H H H Ph -CH (4-F-Ph) Me 1-1204 2-EtSO_Two H H H Ph -CH (4-Cl-Ph) Me 1-1205 2-EtSO_Two H H H Ph 3-Pn 1-1206 2-EtSO_Two H H H 4-Me-Ph 3-Pn 1-1207 2-EtSO_Two H H H Ph -CH (cHx) Me 1-1208 2-EtSO_Two H H H 4-Me-Ph -CH (cHx) Me 1-1209 2-EtSO_Two H H H Ph -CH (4-Br-Ph) Me 1-1210 2-EtSO_Two H H H 4-Me-Ph -CH (4-Br-Ph) Me 1-1211 2-EtSO_Two 4-Me H H Ph -CH (4-Br-Ph) Me 1-1212 2-EtSO_Two 4-F H H Ph -CH (4-Br-Ph) Me 1-1213 2-EtSO_Two H H H Ph -CH_Two(4-H_TwoNOC-Ph) 1-1214 2-EtSO_Two H H H 4-Me-Ph -CH_Two(4-H_TwoNOC-Ph) 1-1215 2-EtSO_Two H H H Ph -CH (1-Np) Me 1-1216 2-EtSO_Two H H H 4-Me-Ph -CH (1-Np) Me 1-1217 3-EtSO_Two H H H Ph iPr 1-1218 3-EtSO_Two H H H Ph Bu 1-1219 3-EtSO_Two H H H Ph tBu 1-1220 3-EtSO_Two H H H Ph nPn 1-1221 3-EtSO_Two H H H Ph 2-Hex 1-1222 3-EtSO_Two H H H Ph 1-Et-Pn 1-1223 3-EtSO_Two 4-Me H H Ph 1-Et-Pn 1-1224 3-EtSO_Two 4-OMe H H Ph 1-Et-Pn 1-1225 3-EtSO_Two 4-OMe 6-OH H Ph 1-Et-Pn 1-1226 3-EtSO_Two 4-OMe 5-F 6-OH Ph 1-Et-Pn 1-1227 3-EtSO_Two 6-OMe H H Ph 1-Et-Pn 1-1228 3-EtSO_Two 4-OH H H Ph 1-Et-Pn 1-1229 3-EtSO_Two 4-F H H Ph 1-Et-Pn 1-1230 3-EtSO_Two 4-Cl H H Ph 1-Et-Pn 1-1231 3-EtSO_Two 4-NH_Two H H Ph 1-Et-Pn 1-1232 3-EtSO_Two 4-NHMe H H Ph 1-Et-Pn 1-1233 3-EtSO_Two 4-N (Me)_Two H H Ph 1-Et-Pn 1-1234 3-EtSO_Two H H H 2-Me-Ph 1-Et-Pn 1-1235 3-EtSO_Two H H H 3-Me-Ph 1-Et-Pn 1-1236 3-EtSO_Two H H H 4-Me-Ph 1-Et-Pn 1-1237 3-EtSO_Two H H H 4-MeO-Ph 1-Et-Pn 1-1238 3-EtSO_Two H H H 4-F -Ph 1-Et-Pn 1-1239 3-EtSO_Two H H H 4-Cl-Ph 1-Et-Pn 1-1240 3-EtSO_Two H H H 1-Et-Pn R^5a= 4-Me-2-MeO-Ph 1-1241 3-EtSO_Two H H H 1-Et-Pn R^5a= 6-F-4-Me-2-MeO-Ph 1-1242 3-EtSO_Two H H H Ph 2-Et-Hx 1-1243 3-EtSO_Two H H H Ph cPn 1-1244 3-EtSO_Two H H H Ph cHx 1-1245 3-EtSO_Two 4-Me H H Ph cHx 1-1246 3-EtSO_Two 4-OMe H H Ph cHx 1-1247 3-EtSO_Two 4-OMe 6-OH H Ph cHx 1-1248 3-EtSO_Two 6-OMe H H Ph cHx 1-1249 3-EtSO_Two 4-OH H H Ph cHx 1-1250 3-EtSO_Two H H H Ph 4-Me-cHx 1-1251 3-EtSO_Two H H H Ph 4-tBu-cHx 1-1252 3-EtSO_Two H H H Ph 4-MeO-cHx 1-1253 3-EtSO_Two H H H Ph 4-F-cHx 1-1254 3-EtSO_Two H H H Ph 4-Cl-cHx 1-1255 3-EtSO_Two H H H Ph 4-HO-cHx 1-1256 3-EtSO_Two H H H Ph 4-HOH_TwoC-cHx 1-1257 3-EtSO_Two H H H Ph -CH_Two-(4-HOH_TwoC-cHx) 1-1258 3-EtSO_Two H H H Ph -CH_Two-(4-HOOC-cHx) 1-1259 3-EtSO_Two H H H Ph -CH_Two-[4- (Me)_TwoNOC-cHx] 1-1260 3-EtSO_Two H H H Ph 1-Inda 1-1261 3-EtSO_Two H H H Ph Bz 1-1262 3-EtSO_Two H H H Ph 4-Me-Bz 1-1263 3-EtSO_Two H H H Ph-(CH_Two)_Two-Ph 1-1264 3-EtSO_Two H H H Ph -CH (Ph) Me 1-1265 3-EtSO_Two 4-Me H H Ph -CH (Ph) Me 1-1266 3-EtSO_Two 4-OMe H H Ph -CH (Ph) Me 1-1267 3-EtSO_Two 4-OMe 6-OH H Ph -CH (Ph) Me 1-1268 3-EtSO_Two 4-OMe 5-F 6-OH Ph -CH (Ph) Me 1-1269 3-EtSO_Two 6-OMe H H Ph -CH (Ph) Me 1-1270 3-EtSO_Two 4-OH H H Ph -CH (Ph) Me 1-1271 3-EtSO_Two 4-F H H Ph -CH (Ph) Me 1-1272 3-EtSO_Two 4-Cl H H Ph -CH (Ph) Me 1-1273 3-EtSO_Two 4-NH_Two H H Ph -CH (Ph) Me 1-1274 3-EtSO_Two 4-NHMe H H Ph -CH (Ph) Me 1-1275 2-EtSO_Two 4-N (Me)_Two H H Ph -CH (Ph) Me 1-1276 3-EtSO_Two H H H 2-Me-Ph -CH (Ph) Me 1-1277 3-EtSO_Two H H H 3-Me-Ph -CH (Ph) Me 1-1278 3-EtSO_Two H H H 4-Me-Ph -CH (Ph) Me 1-1279 3-EtSO_Two H H H 4-MeO-Ph -CH (Ph) Me 1-1280 3-EtSO_Two H H H 4-F -Ph -CH (Ph) Me 1-1281 3-EtSO_Two H H H 4-Cl-Ph -CH (Ph) Me 1-1282 3-EtSO_Two H H H -CH (Ph) Me R^5a= 4-Me-2-MeO-Ph 1-1283 3-EtSO_Two H H H -CH (Ph) Me R^5a= 6-F-4-Me-2-MeO-Ph 1-1284 3-EtSO_Two H H H Ph -CH (4-Me-Ph) Me 1-1285 3-EtSO_Two H H H Ph -CH (4-MeO-Ph) Me 1-1286 3-EtSO_Two H H H Ph -CH (4-F-Ph) Me 1-1287 3-EtSO_Two H H H Ph -CH (4-Cl-Ph) Me 1-1288 3-EtSO_Two H H H Ph 3-Pn 1-1289 3-EtSO_Two H H H 4-Me-Ph 3-Pn 1-1290 3-EtSO_Two H H H Ph -CH (cHx) Me 1-1291 3-EtSO_Two H H H 4-Me-Ph -CH (cHx) Me 1-1292 3-EtSO_Two H H H Ph -CH (4-Br-Ph) Me 1-1293 3-EtSO_Two H H H 4-Me-Ph -CH (4-Br-Ph) Me 1-1294 3-EtSO_Two 4-Me H H Ph -CH (4-Br-Ph) Me 1-1295 3-EtSO_Two 4-F H H Ph -CH (4-Br-Ph) Me 1-1296 3-EtSO_Two H H H Ph -CH_Two(4-H_TwoNOC-Ph) 1-1297 3-EtSO_Two H H H 4-Me-Ph -CH_Two(4-H_TwoNOC-Ph) 1-1298 3-EtSO_Two H H H Ph -CH (1-Np) Me 1-1299 3-EtSO_Two H H H 4-Me-Ph -CH (1-Np) Me 1-1300 4-EtSO_Two H H H Ph iPr 1-1301 4-EtSO_Two H H H Ph Bu 1-1302 4-EtSO_Two H H H Ph tBu 1-1303 4-EtSO_Two H H H Ph nPn 1-1304 4-EtSO_Two H H H Ph 2-Hex 1-1305 4-EtSO_Two H H H Ph 1-Et-Pn 1-1306 4-EtSO_Two 2-Me H H Ph 1-Et-Pn 1-1307 4-EtSO_Two 2-OMe H H Ph 1-Et-Pn 1-1308 4-EtSO_Two 2-OMe 6-OH H Ph 1-Et-Pn 1-1309 4-EtSO_Two 2-OMe 5-F 6-OH Ph 1-Et-Pn 1-1310 4-EtSO_Two 6-OMe H H Ph 1-Et-Pn 1-1311 4-EtSO_Two 2-OH H H Ph 1-Et-Pn 1-1312 4-EtSO_Two 2-F H H Ph 1-Et-Pn 1-1313 4-EtSO_Two 2-Cl H H Ph 1-Et-Pn 1-1314 4-EtSO_Two 2-NH_Two H H Ph 1-Et-Pn 1-1315 4-EtSO_Two 2-NHMe H H Ph 1-Et-Pn 1-1316 4-EtSO_Two 2-N (Me)_Two H H Ph 1-Et-Pn 1-1317 4-EtSO_Two H H H 2-Me-Ph 1-Et-Pn 1-1318 4-EtSO_Two H H H 3-Me-Ph 1-Et-Pn 1-1319 4-EtSO_Two H H H 4-Me-Ph 1-Et-Pn 1-1320 4-EtSO_Two H H H 4-MeO-Ph 1-Et-Pn 1-1321 4-EtSO_Two H H H 4-F -Ph 1-Et-Pn 1-1322 4-EtSO_Two H H H 4-Cl-Ph 1-Et-Pn 1-1323 4-EtSO_Two H H H 1-Et-Pn R^5a= 4-Me-2-MeO-Ph 1-1324 4-EtSO_Two H H H 1-Et-Pn R^5a= 6-F-4-Me-2-MeO-Ph 1-1325 4-EtSO_Two H H H Ph 2-Et-Hx 1-1326 4-EtSO_Two H H H Ph cPn 1-1327 4-EtSO_Two H H H Ph cHx 1-1328 4-EtSO_Two 2-Me H H Ph cHx 1-1329 4-EtSO_Two 2-OMe H H Ph cHx 1-1330 4-EtSO_Two 2-OMe 6-OH H Ph cHx 1-1331 4-EtSO_Two 6-OMe H H Ph cHx 1-1332 4-EtSO_Two 2-OH H H Ph cHx 1-1333 4-EtSO_Two H H H Ph 4-Me-cHx 1-1334 4-EtSO_Two H H H Ph 4-tBu-cHx 1-1335 4-EtSO_Two H H H Ph 4-MeO-cHx 1-1336 4-EtSO_Two H H H Ph 4-F-cHx 1-1337 4-EtSO_Two H H H Ph 4-Cl-cHx 1-1338 4-EtSO_Two H H H Ph 4-HO-cHx 1-1339 4-EtSO_Two H H H Ph 4-HOH_TwoC-cHx 1-1340 4-EtSO_Two H H H Ph -CH_Two-(4-HOH_TwoC-cHx) 1-1341 4-EtSO_Two H H H Ph -CH_Two-(4-HOOC-cHx) 1-1342 4-EtSO_Two H H H Ph -CH_Two-[4- (Me)_TwoNOC-cHx] 1-1343 4-EtSO_Two H H H Ph 1-Inda 1-1344 4-EtSO_Two H H H Ph 4-Me-Bz 1-1345 4-EtSO_Two H H H Ph-(CH_Two)_Two-Ph 1-1346 4-EtSO_Two H H H Ph -CH (Ph) Me 1-1347 4-EtSO_Two 2-Me H H Ph -CH (Ph) Me 1-1348 4-EtSO_Two 2-OMe H H Ph -CH (Ph) Me 1-1349 4-EtSO_Two 2-OMe 6-OH H Ph -CH (Ph) Me 1-1350 4-EtSO_Two 2-OMe 5-F 6-OH Ph -CH (Ph) Me 1-1351 4-EtSO_Two 6-OMe H H Ph -CH (Ph) Me 1-1352 4-EtSO_Two 2-OH H H Ph -CH (Ph) Me 1-1353 4-EtSO_Two 2-F H H Ph -CH (Ph) Me 1-1354 4-EtSO_Two 2-Cl H H Ph -CH (Ph) Me 1-1355 4-EtSO_Two 2-NH_Two H H Ph -CH (Ph) Me 1-1356 4-EtSO_Two 2-NHMe H H Ph -CH (Ph) Me 1-1357 4-EtSO_Two 2-N (Me)_Two H H Ph -CH (Ph) Me 1-1358 4-EtSO_Two H H H 2-Me-Ph -CH (Ph) Me 1-1359 4-EtSO_Two H H H 3-Me-Ph -CH (Ph) Me 1-1360 4-EtSO_Two H H H 4-Me-Ph -CH (Ph) Me 1-1361 4-EtSO_Two H H H 4-MeO-Ph -CH (Ph) Me 1-1362 4-EtSO_Two H H H 4-F -Ph -CH (Ph) Me 1-1363 4-EtSO_Two H H H 4-Cl-Ph -CH (Ph) Me 1-1364 4-EtSO_Two H H H -CH (Ph) Me R^5a= 4-Me-2-MeO-Ph 1-1365 4-EtSO_Two H H H -CH (Ph) Me R^5a= 4-Me-6-F-2-MeO-Ph 1-1366 4-EtSO_Two H H H Ph -CH (4-Me-Ph) Me 1-1367 4-EtSO_Two H H H Ph -CH (4-MeO-Ph) Me 1-1368 4-EtSO_Two H H H Ph -CH (4-F-Ph) Me 1-1369 4-EtSO_Two H H H Ph -CH (4-Cl-Ph) Me 1-1370 4-EtSO_Two H H H Ph 3-Pn 1-1371 4-EtSO_Two H H H 4-Me-Ph 3-Pn 1-1372 4-EtSO_Two H H H Ph -CH (cHx) Me 1-1373 4-EtSO_Two H H H 4-Me-Ph -CH (cHx) Me 1-1374 4-EtSO_Two H H H Ph -CH (4-Br-Ph) Me 1-1375 4-EtSO_Two H H H 4-Me-Ph -CH (4-Br-Ph) Me 1-1376 4-EtSO_Two 2-Me H H Ph -CH (4-Br-Ph) Me 1-1377 4-EtSO_Two 2-F H H Ph -CH (4-Br-Ph) Me 1-1378 4-EtSO_Two H H H Ph -CH_Two(4-H_TwoNOC-Ph) 1-1379 4-EtSO_Two H H H 4-Me-Ph -CH_Two(4-H_TwoNOC-Ph) 1-1380 4-EtSO_Two H H H Ph -CH (1-Np) Me 1-1381 4-EtSO_Two H H H 4-Me-Ph -CH (1-Np) Me 1-1382 2-PrSO_Two H H H Ph tBu 1-1383 2-PrSO_Two H H H Ph 1-Et-Pn 1-1384 2-PrSO_Two H H H Ph 2-Et-Hx 1-1385 2-PrSO_Two H H H Ph cHx 1-1386 2-PrSO_Two H H H Ph 4-Me-cHx 1-1387 2-PrSO_Two H H H Ph Bz 1-1388 2-PrSO_Two H H H Ph -CH (Ph) Me 1-1389 2-PrSO_Two H H H Ph -CH (4-Me-Ph) Me 1-1390 2-PrSO_Two H H H Ph -CH (4-Br-Ph) Me 1-1391 3-PrSO_Two H H H Ph tBu 1-1392 3-PrSO_Two H H H Ph 1-Et-Pn 1-1393 3-PrSO_Two H H H Ph 2-Et-Hx 1-1394 3-PrSO_Two H H H Ph cHx 1-1395 3-PrSO_Two H H H Ph 4-Me-cHx 1-1396 3-PrSO_Two H H H Ph Bz 1-1397 3-PrSO_Two H H H Ph -CH (Ph) Me 1-1398 3-PrSO_Two H H H Ph -CH (4-Me-Ph) Me 1-1399 3-PrSO_Two H H H Ph -CH (4-Br-Ph) Me 1-1400 4-PrSO_Two H H H Ph tBu 1-1401 4-PrSO_Two H H H Ph 1-Et-Pn 1-1402 4-PrSO_Two H H H Ph 2-Et-Hx 1-1403 4-PrSO_Two H H H Ph cHx 1-1404 4-PrSO_Two H H H Ph 4-Me-cHx 1-1405 4-PrSO_Two H H H Ph Bz 1-1406 4-PrSO_Two H H H Ph -CH (Ph) Me 1-1407 4-PrSO_Two H H H Ph -CH (4-Me-Ph) Me 1-1408 4-PrSO_Two H H H Ph -CH (4-Br-Ph) Me 1-1409 2-BuSO_Two H H H Ph iPr 1-1410 2-BuSO_Two H H H Ph Bu 1-1411 2-BuSO_Two H H H Ph tBu 1-1412 2-BuSO_Two H H H Ph nPn 1-1413 2-BuSO_Two H H H Ph 2-Hx 1-1414 2-BuSO_Two H H H Ph 1-Et-Pn 1-1415 2-BuSO_Two 4-Me H H Ph 1-Et-Pn 1-1416 2-BuSO_Two 4-OMe H H Ph 1-Et-Pn 1-1417 2-BuSO_Two 4-OMe 6-OH H Ph 1-Et-Pn 1-1419 2-BuSO_Two 6-OMe H H Ph 1-Et-Pn 1-1420 2-BuSO_Two 4-OH H H Ph 1-Et-Pn 1-1421 2-BuSO_Two 4-F H H Ph 1-Et-Pn 1-1422 2-BuSO_Two 4-Cl H H Ph 1-Et-Pn 1-1423 2-BuSO_Two 4-NH_Two H H Ph 1-Et-Pn 1-1424 2-BuSO_Two 4-NHMe H H Ph 1-Et-Pn 1-1425 2-BuSO_Two 4-N (Me)_Two H H Ph 1-Et-Pn 1-1426 2-BuSO_Two H H H 2-Me-Ph 1-Et-Pn 1-1427 2-BuSO_Two H H H 3-Me-Ph 1-Et-Pn 1-1428 2-BuSO_Two H H H 4-Me-Ph 1-Et-Pn 1-1429 2-BuSO_Two H H H 4-MeO-Ph 1-Et-Pn 1-1430 2-BuSO_Two H H H 4-F -Ph 1-Et-Pn 1-1431 2-BuSO_Two H H H 4-Cl-Ph 1-Et-Pn 1-1432 2-BuSO_Two H H H 1-Et-Pn R^5a= 4-Me-2-MeO-Ph 1-1433 2-BuSO_Two H H H 1-Et-Pn R^5a= 6-F-4-Me-2-MeO-Ph 1-1434 2-BuSO_Two H H H Ph 2-Et-Hx 1-1435 2-BuSO_Two H H H Ph cPn 1-1436 2-BuSO_Two H H H Ph cHx 1-1437 2-BuSO_Two 4-Me H H Ph cHx 1-1438 2-BuSO_Two 4-OMe H H Ph cHx 1-1439 2-BuSO_Two 4-OMe 6-OH H Ph cHx 1-1440 2-BuSO_Two 6-OMe H H Ph cHx 1-1441 2-BuSO_Two 4-OH H H Ph cHx 1-1442 2-BuSO_Two H H H Ph 4-Me-cHx 1-1443 2-BuSO_Two H H H Ph 4-tBu-cHx 1-1444 2-BuSO_Two H H H Ph 4-MeO-cHx 1-1445 2-BuSO_Two H H H Ph 4-F-cHx 1-1446 2-BuSO_Two H H H Ph 4-Cl-cHx 1-1447 2-BuSO_Two H H H Ph 4-HO-cHx 1-1448 2-BuSO_Two H H H Ph 4-HOH_TwoC-cHx 1-1449 2-BuSO_Two H H H Ph -CH_Two-(4-HOH_TwoC-cHx) 1-1450 2-BuSO_Two H H H Ph -CH_Two-(4-HOOC-cHx) 1-1451 2-BuSO_Two H H H Ph -CH_Two-[4- (Me)_TwoNOC-cHx] 1-1452 2-BuSO_Two H H H Ph 1-Inda 1-1453 2-BuSO_Two H H H Ph Bz 1-1454 2-BuSO_Two H H H Ph 4-Me-Bz 1-1455 2-BuSO_Two H H H Ph-(CH_Two)_Two-Ph 1-1456 2-BuSO_Two H H H Ph -CH (Ph) Me 1-1457 2-BuSO_Two 4-Me H H Ph -CH (Ph) Me 1-1458 2-BuSO_Two 4-OMe H H Ph -CH (Ph) Me 1-1459 2-BuSO_Two 4-OMe 6-OH H Ph -CH (Ph) Me 1-1460 2-BuSO_Two 4-OMe 5-F 6-OH Ph -CH (Ph) Me 1-1461 2-BuSO_Two 6-OMe H H Ph -CH (Ph) Me 1-1462 2-BuSO_Two 4-OH H H Ph -CH (Ph) Me 1-1463 2-BuSO_Two 4-F H H Ph -CH (Ph) Me 1-1464 2-BuSO_Two 4-Cl H H Ph -CH (Ph) Me 1-1465 2-BuSO_Two 4-NH_Two H H Ph -CH (Ph) Me 1-1466 2-BuSO_Two 4-NHMe H H Ph -CH (Ph) Me 1-1467 2-BuSO_Two 4-N (Me)_Two H H Ph -CH (Ph) Me 1-1468 2-BuSO_Two H H H 2-Me-Ph -CH (Ph) Me 1-1469 2-BuSO_Two H H H 3-Me-Ph -CH (Ph) Me 1-1470 2-BuSO_Two H H H 4-Me-Ph -CH (Ph) Me 1-1471 2-BuSO_Two H H H 4-MeO-Ph -CH (Ph) Me 1-1472 2-BuSO_Two H H H 4-F -Ph -CH (Ph) Me 1-1473 2-BuSO_Two H H H 4-Cl-Ph -CH (Ph) Me R^5a= 4-Me-2-MeO-Ph 1-1475 2-BuSO_Two H H H -CH (Ph) Me R^5a= 6-F-4-Me-2-MeO-Ph 1-1476 2-BuSO_Two H H H Ph -CH (4-Me-Ph) Me 1-1477 2-BuSO_Two H H H Ph -CH (4-MeO-Ph) Me 1-1478 2-BuSO_Two H H H Ph -CH (4-F-Ph) Me 1-1479 2-BuSO_Two H H H Ph -CH (4-Cl-Ph) Me 1-1480 2-BuSO_Two H H H Ph 3-Pn 1-1481 2-BuSO_Two H H H 4-Me-Ph 3-Pn 1-1482 2-BuSO_Two H H H Ph -CH (cHx) Me 1-1483 2-BuSO_Two H H H 4-Me-Ph -CH (cHx) Me 1-1484 2-BuSO_Two H H H Ph -CH (4-Br-Ph) Me 1-1485 2-BuSO_Two H H H 4-Me-Ph -CH (4-Br-Ph) Me 1-1486 2-BuSO_Two 4-Me H H Ph -CH (4-Br-Ph) Me 1-1487 2-BuSO_Two 4-F H H Ph -CH (4-Br-Ph) Me 1-1488 2-BuSO_Two H H H Ph -CH_Two(4-H_TwoNOC-Ph) 1-1489 2-BuSO_Two H H H 4-Me-Ph -CH_Two(4-H_TwoNOC-Ph) 1-1490 2-BuSO_Two H H H Ph -CH (1-Np) Me 1-1491 2-BuSO_Two H H H 4-Me-Ph -CH (1-Np) Me 1-1492 3-BuSO_Two H H H Ph tBu 1-1493 3-BuSO_Two H H H Ph 1-Et-Pn 1-1494 3-BuSO_Two H H H Ph 2-Et-Hx 1-1495 3-BuSO_Two H H H Ph cHx 1-1496 3-BuSO_Two H H H Ph 4-Me-cHx 1-1497 3-BuSO_Two H H H Ph Bz 1-1498 3-BuSO_Two H H H Ph -CH (Ph) Me 1-1499 3-BuSO_Two H H H Ph -CH (4-Me-Ph) Me 1-1500 3-BuSO_Two H H H Ph -CH (4-Br-Ph) Me 1-1502 4-BuSO_Two H H H Ph 1-Et-Pn 1-1503 4-BuSO_Two H H H Ph 2-Et-Hx 1-1504 4-BuSO_Two H H H Ph cHx 1-1505 4-BuSO_Two H H H Ph 4-Me-cHx 1-1506 4-BuSO_Two H H H Ph Bz 1-1507 4-BuSO_Two H H H Ph -CH (Ph) Me 1-1508 4-BuSO_Two H H H Ph -CH (4-Me-Ph) Me 1-1509 4-BuSO_Two H H H Ph -CH (4-Br-Ph) Me 1-1510 2-PhSO_Two H H H Ph iPr 1-1511 2-PhSO_Two H H H Ph Bu 1-1512 2-PhSO_Two H H H Ph tBu 1-1513 2-PhSO_Two H H H Ph nPn 1-1514 2-PhSO_Two H H H Ph 1-Et-Pn 1-1515 2-PhSO_Two 4-Me H H Ph 1-Et-Pn 1-1516 2-PhSO_Two 4-OMe H H Ph 1-Et-Pn 1-1517 2-PhSO_Two 4-OMe 6-OH H Ph 1-Et-Pn 1-1518 2-PhSO_Two 6-OMe H H Ph 1-Et-Pn 1-1519 2-PhSO_Two 4-OH H H Ph 1-Et-Pn 1-1520 2-PhSO_Two H H H Ph 2-Et-Hx 1-1521 2-PhSO_Two H H H Ph cPn 1-1522 2-PhSO_Two H H H Ph cHx 1-1523 2-PhSO_Two H H H Ph 4-MeO-cHx 1-1524 2-PhSO_Two H H H Ph 4-F-cHx 1-1525 2-PhSO_Two H H H Ph 4-Cl-cHx 1-1526 2-PhSO_Two H H H Ph 4-HO-cHx 1-1527 2-PhSO_Two H H H Ph 4-HOH_TwoC-cHx 1-1528 2-PhSO_Two H H H Ph 4-Me-cHx 1-1529 2-PhSO_Two H H H Ph 4-tBu-cHx 1-1530 2-PhSO_Two H H H Ph Bz 1-1531 2-PhSO_Two H H H Ph-(CH_Two)_Two-Ph 1-1532 2-PhSO_Two H H H Ph -CH (Ph) Me 1-1533 2-PhSO_Two 4-Me H H Ph -CH (Ph) Me 1-1534 2-PhSO_Two 4-OMe H H Ph -CH (Ph) Me 1-1535 2-PhSO_Two 4-OMe 6-OH H Ph -CH (Ph) Me 1-1536 2-PhSO_Two 6-OMe H H Ph -CH (Ph) Me 1-1537 2-PhSO_Two 4-OH H H Ph -CH (Ph) Me 1-1538 2-PhSO_Two H H H Ph 1-Inda 1-1539 2-PhSO_Two H H H Ph -CH (cHx) Me 1-1540 2-PhSO_Two H H H Ph -CH (4-Br-Ph) Me 1-1541 2-PhSO_Two H H H Ph -CH (1-Np) Me 1-1542 2- (2-Tol) SO_Two H H H Ph tBu 1-1543 2- (2-Tol) SO_Two H H H Ph 1-Et-Pn 1-1544 2- (2-Tol) SO_Two H H H Ph cHx 1-1545 2- (2-Tol) SO_Two H H H Ph -CH (Ph) Me 1-1546 2- (2-Et-Ph) SO_Two H H H Ph tBu 1-1547 2- (2-MeO-Ph) SO_Two H H H Ph tBu 1-1548 2- (2-F-Ph) SO_Two H H H Ph tBu 1-1549 2- (2-Cl-Ph) SO_Two H H H Ph tBu 1-1550 2- (3-Tol) SO_Two H H H Ph tBu 1-1551 2- (3-Tol) SO_Two H H H Ph 1-Et-Pn 1-1552 2- (3-Tol) SO_Two H H H Ph cHx 1-1553 2- (3-Tol) SO_Two H H H Ph -CH (Ph) Me 1-1554 2- (3-Et-Ph) SO_Two H H H Ph tBu 1-1555 2- (3-MeO-Ph) SO_Two H H H Ph tBu 1-1556 2- (3-F-Ph) SO_Two H H H Ph tBu 1-1557 2- (3-Cl-Ph) SO_Two H H H Ph tBu 1-1558 2- (4-Tol) SO_Two H H H Ph tBu 1-1559 2- (4-Tol) SO_Two H H H Ph 1-Et-Pn 1-1560 2- (4-Tol) SO_Two H H H Ph cHx 1-1561 2- (4-Tol) SO_Two H H H Ph Bz 1-1562 2- (4-Tol) SO_Two H H H Ph -CH (Ph) Me 1-1563 2- (4-Et-Ph) SO_Two H H H Ph tBu 1-1564 2- (4-MeO-Ph) SO_Two H H H Ph tBu 1-1565 2- (4-F-Ph) SO_Two H H H Ph tBu 1-1566 2- (4-Cl-Ph) SO_Two H H H Ph tBu 1-1567 3-PhSO_Two H H H Ph tBu 1-1568 3-PhSO_Two H H H Ph 1-Et-Pn 1-1569 3-PhSO_Two H H H Ph 2-Et-Hx 1-1570 3-PhSO_Two H H H Ph cHx 1-1571 3-PhSO_Two H H H Ph 4-Me-cHx 1-1572 3-PhSO_Two H H H Ph Bz 1-1573 3-PhSO_Two H H H Ph -CH (Ph) Me 1-1574 3-PhSO_Two H H H Ph -CH (4-Me-Ph) Me 1-1575 3- (4-Tol) SO_Two H H H Ph tBu 1-1576 3- (4-MeO-Ph) SO_Two H H H Ph tBu 1-1577 3- (4-F-Ph) SO_Two H H H Ph tBu 1-1578 3- (4-Cl-Ph) SO_Two H H H Ph tBu 1-1579 3-PhSO_Two H H H Ph -CH (4-Br-Ph) Me 1-1580 4-PhSO_Two H H H Ph tBu 1-1581 4-PhSO_Two H H H Ph 1-Et-Pn 1-1582 4-PhSO_Two H H H Ph 2-Et-Hx 1-1583 4-PhSO_Two H H H Ph cHx 1-1584 4-PhSO_Two H H H Ph 4-Me-cHx 1-1585 4-PhSO_Two H H H Ph Bz 1-1586 4-PhSO_Two H H H Ph -CH (Ph) Me 1-1587 4-PhSO_Two H H H Ph -CH (4-Me-Ph) Me 1-1588 4-PhSO_Two H H H Ph -CH (4-Br-Ph) Me 1-1589 4- (4-Tol) SO_Two H H H Ph tBu 1-1590 4- (4-MeO-Ph) SO_Two H H H Ph tBu 1-1591 4- (4-F-Ph) SO_Two H H H Ph tBu 1-1592 4- (4-Cl-Ph) SO_Two H H H Ph tBu 1-1593 2-PhSO_Two H H H 4-Me-Ph -CH (Ph) Me 1-1594 3-PhSO_Two H H H 4-Me-Ph -CH (Ph) Me 1-1595 4-PhSO_Two H H H 4-Me-Ph -CH (Ph) Me 1-1596 2-MeHNSO_Two H H H Ph cHx 1-1597 3-MeHNSO_Two H H H Ph cHx 1-1598 4-MeHNSO_Two H H H Ph cHx 1-1599 4-EtHNSO_Two H H H Ph cHx 1-1600 2- (Me)_TwoNSO_Two H H H Ph cHx 1-1601 3- (Me)_TwoNSO_Two H H H Ph cHx 1-1602 3- (Me)_TwoNSO_Two 4-OMe 6-OH H Ph cHx 1-1603 4- (Me)_TwoNSO_Two H H H Ph cHx 1-1604 4- (Et)_TwoNSO_Two HHH Ph cHx 1-1605 2-MeSO HHH Ph 1-Et-Pn 1-1606 2-MeSO HHH Ph 2-Et-Hx 1-1607 2-MeSO HHH Ph cHx 1-1608 2-MeSO HHH Ph Bz 1-1609 2-MeSO HHH Ph -CH (Ph) Me 1-1610 3-MeSO HHH Ph 1-Et-Pn 1-1611 3-MeSO HHH Ph 2-Et-Hx 1-1612 3-MeSO HHH Ph cHx 1-1613 3 -MeSO HHH Ph Bz 1-1614 3-MeSO HHH Ph -CH (Ph) Me 1-1615 4-MeSO HHH Ph 1-Et-Pn 1-1616 4-MeSO HHH Ph 2-Et-Hx 1-1617 4- MeSO HHH Ph cHx 1-1618 4-MeSO HHH Ph Bz 1-1619 4-MeSO HHH Ph -CH (Ph) Me 1-1620 2-EtSO HHH Ph 1-Et-Pn 1-1621 2-EtSO HHH Ph 2- Et-Hx 1-1622 2-EtSO HHH Ph cHx 1-1623 2-EtSO HHH Ph Bz 1-1624 2-EtSO HHH Ph -CH (Ph) Me 1-1625 3-EtSO HHH Ph 1-Et-Pn 1- 1626 3-EtSO HHH Ph 2-Et-Hx 1-1627 3-EtSO HHH Ph cHx 1-1628 3-EtSO HHH Ph Bz 1-1629 3-EtSO HHH Ph -CH (Ph) Me 1-1630 4-EtSO HHH Ph 1-Et-Pn 1-1631 4-EtSO HHH Ph 2-Et-Hx 1-1632 4-EtSO HHH Ph cHx 1-1633 4-EtSO HHH Ph Bz 1-1634 4-EtSO HHH Ph -CH (Ph) Me 1-1635 2-PrSO HHH Ph 1-Et-Pn 1-1636 2-PrSO HHH Ph cHx 1-1637 2-PrSO HHH Ph -CH (Ph) Me 1-1638 3-PrSO HHH Ph 1-Et-Pn 1-1639 3-PrSO HHH Ph cHx 1-1640 3-PrSO HHH Ph -CH (Ph) Me 1-1641 4-PrSO HHH Ph 1-Et-Pn 1-1642 4 -PrSO HHH Ph cHx 1-1643 4-PrSO HHH Ph -CH (Ph) Me 1-1644 2-BuSO HHH Ph 1-Et-Pn 1-1645 2-BuSO HHH Ph cHx 1-1646 2-BuSO HHH Ph- CH (Ph) Me 1-1647 3-BuSO HHH Ph 1-Et-Pn 1-1648 3-BuSO HHH Ph cHx 1-1649 3-BuSO HHH Ph -CH (Ph) Me 1-1650 4-BuSO HHH Ph 1 -Et-Pn 1-1651 4-BuSO HHH Ph cHx 1-1652 4-BuSO HHH Ph -CH (Ph) Me 1-1653 2-PhOCHN HHH Ph 1-Et-Pn 1-1654 2-PhOCHN HHH Ph cHx 1 -1655 2-PhOCHN HHH Ph -CH (Ph) Me 1-1656 3-PhOCHN HHH Ph 1-Et-Pn 1-1657 3-PhOCHN HHH Ph 2-Et-Hx 1-1658 3-PhOCHN HHH Ph cHx 1- 1659 3-PhOCHN HHH Ph Bz 1-1660 3-PhOCHN HHH Ph -CH (Ph) Me 1-1661 3- (4-Tol) OCHN HHH Ph -CH (Ph) Me 1-1662 4-PhOCHN HHH Ph 1- Et-Pn 1-1663 4-PhOCHN HHH Ph cHx 1-1664 4-PhOCHN HHH Ph -CH (Ph) Me 1-1665 2-TzOCHN HHH Ph 1-Et-Pn 1-1666 2-TzOCHN HHH Ph cHx 1- 1667 2-TzOCHN HHH Ph -CH (Ph) Me 1-1668 3-TzOCHN HHH Ph 1-Et-Pn 1-1669 3-TzOCHN HHH Ph 2-E t-Hx 1-1670 3-TzOCHN HHH Ph cHx 1-1671 3-TzOCHN HHH Ph Bz 1-1672 3-TzOCHN HHH Ph -CH (Ph) Me 1-1673 4-TzOCHN HHH Ph 1-Et-Pn 1- 1674 4-TzOCHN HHH Ph cHx 1-1675 4-TzOCHN HHH Ph -CH (Ph) Me 1-1676 2- (2-Tol) SO_TwoHNOCHN H H H Ph tBu 1-1677 2- (2-Tol) SO_TwoHNOCHN H H H Ph 1-Et-Pn 1-1678 2- (2-Tol) SO_TwoHNOCHN H H H Ph 2-Et-Hx 1-1679 2- (2-Tol) SO_TwoHNOCHN H H H Ph cHx 1-1680 2- (2-Tol) SO_TwoHNOCHN H H H Ph 4-Me-cHx 1-1681 2- (2-Tol) SO_TwoHNOCHN H H H Ph Bz 1-1682 2- (2-Tol) SO_TwoHNOCHN H H H Ph -CH (Ph) Me 1-1683 2- (2-Tol) SO_TwoHNOCHN H H H Ph -CH (4-Me-Ph) Me 1-1684 2- (3-Tol) SO_TwoHNOCHN H H H Ph tBu 1-1685 2- (3-Tol) SO_TwoHNOCHN H H H Ph 1-Et-Pn 1-1686 2- (3-Tol) SO_TwoHNOCHN H H H Ph 2-Et-Hx 1-1687 2- (3-Tol) SO_TwoHNOCHN H H H Ph cHx 1-1688 2- (3-Tol) SO_TwoHNOCHN H H H Ph 4-Me-cHx 1-1689 2- (3-Tol) SO_TwoHNOCHN H H H Ph Bz 1-1690 2- (3-Tol) SO_TwoHNOCHN H H H Ph -CH (Ph) Me 1-1691 2- (3-Tol) SO_TwoHNOCHN H H H Ph -CH (4-Me-Ph) Me 1-1692 2- (4-Tol) SO_TwoHNOCHN H H H Ph iPr 1-1693 2- (4-Tol) SO_TwoHNOCHN H H H Ph Bu 1-1694 2- (4-Tol) SO_TwoHNOCHN H H H Ph tBu 1-1695 2- (4-Tol) SO_TwoHNOCHN H H H Ph nPn 1-1696 2- (4-Tol) SO_TwoHNOCHN H H H Ph 2-Hex 1-1697 2- (4-Tol) SO_TwoHNOCHN H H H Ph 1-Et-Pn 1-1698 2- (4-Tol) SO_TwoHNOCHN 4-Me H H Ph 1-Et-Pn 1-1699 2- (4-Tol) SO_TwoHNOCHN 4-OMe H H Ph 1-Et-Pn 1-1700 2- (4-Tol) SO_TwoHNOCHN 4-OMe 6-OH H Ph 1-Et-Pn 1-1701 2- (4-Tol) SO_TwoHNOCHN 4-OMe 5-F 6-OH Ph 1-Et-Pn 1-1702 2- (4-Tol) SO_TwoHNOCHN 6-OMe H H Ph 1-Et-Pn 1-1703 2- (4-Tol) SO_TwoHNOCHN 4-OH H H Ph 1-Et-Pn 1-1705 2- (4-Tol) SO_TwoHNOCHN 4-Cl H H Ph 1-Et-Pn 1-1706 2- (4-Tol) SO_TwoHNOCHN 4-NH_Two H H Ph 1-Et-Pn 1-1707 2- (4-Tol) SO_TwoHNOCHN 4-NHMe H H Ph 1-Et-Pn 1-1708 2- (4-Tol) SO_TwoHNOCHN 4-N (Me)_Two H H Ph 1-Et-Pn 1-1709 2- (4-Tol) SO_TwoHNOCHN H H H 2-Me 1-Et-Pn 1-1710 2- (4-Tol) SO_TwoHNOCHN H H H 3-Me 1-Et-Pn 1-1711 2- (4-Tol) SO_TwoHNOCHN H H H 4-Me 1-Et-Pn 1-1712 2- (4-Tol) SO_TwoHNOCHN H H H 4-OMe 1-Et-Pn 1-1713 2- (4-Tol) SO_TwoHNOCHN H H H 4-F 1-Et-Pn 1-1714 2- (4-Tol) SO_TwoHNOCHN H H H 4-Cl 1-Et-Pn 1-1715 2- (4-Tol) SO_TwoHNOCHN H H H 1-Et-Pn R^5a= 4-Me-2-MeO-Ph 1-1716 2- (4-Tol) SO_TwoHNOCHN H H H 1-Et-Pn R^5a= 6-F-4-Me-2-MeO-Ph 1-1717 2- (4-Tol) SO_TwoHNOCHN H H H Ph 2-Et-Hx 1-1718 2- (4-Tol) SO_TwoHNOCHN H H H Ph cPn 1-1719 2- (4-Tol) SO_TwoHNOCHN H H H Ph cHx 1-1720 2- (4-Tol) SO_TwoHNOCHN 4-Me H H Ph cHx 1-1721 2- (4-Tol) SO_TwoHNOCHN 4-OMe H H Ph cHx 1-1722 2- (4-Tol) SO_TwoHNOCHN 4-OMe 6-OH H Ph cHx 1-1723 2- (4-Tol) SO_TwoHNOCHN 6-OMe H H Ph cHx 1-1724 2- (4-Tol) SO_TwoHNOCHN 4-OH H H Ph cHx 1-1725 2- (4-Tol) SO_TwoHNOCHN H H H Ph 4-Me-cHx 1-1726 2- (4-Tol) SO_TwoHNOCHN H H H Ph 4-tBu-cHx 1-1727 2- (4-Tol) SO_TwoHNOCHN H H H Ph 4-MeO-cHx 1-1728 2- (4-Tol) SO_TwoHNOCHN H H H Ph 4-F-cHx 1-1729 2- (4-Tol) SO_TwoHNOCHN H H H Ph 4-Cl-cHx 1-1730 2- (4-Tol) SO_TwoHNOCHN H H H Ph 4-HO-cHx 1-1731 2- (4-Tol) SO_TwoHNOCHN H H H Ph 4-HOH_TwoC-cHx 1-1732 2- (4-Tol) SO_TwoHNOCHN H H H Ph -CH_Two-(4-HOH_TwoC-cHx) 1-1733 2- (4-Tol) SO_TwoHNOCHN H H H Ph -CH_Two-(4-HOOC-cHx) 1-1734 2- (4-Tol) SO_TwoHNOCHN H H H Ph -CH_Two-[4- (Me)_TwoNOC-cHx] 1-1735 2- (4-Tol) SO_TwoHNOCHN H H H Ph 1-Inda 1-1736 2- (4-Tol) SO_TwoHNOCHN H H H Ph Bz 1-1737 2- (4-Tol) SO_TwoHNOCHN H H H Ph 4-Me-Bz 1-1738 2- (4-Tol) SO_TwoHNOCHN H H H Ph-(CH_Two)_Two-Ph 1-1739 2- (4-Tol) SO_TwoHNOCHN H H H Ph -CH (Ph) Me 1-1740 2- (4-Tol) SO_TwoHNOCHN 4-Me H H Ph -CH (Ph) Me 1-1741 2- (4-Tol) SO_TwoHNOCHN 4-OMe H H Ph -CH (Ph) Me 1-1742 2- (4-Tol) SO_TwoHNOCHN 4-OMe 6-OH H Ph -CH (Ph) Me 1-1743 2- (4-Tol) SO_TwoHNOCHN 4-OMe 5-F 6-OH Ph -CH (Ph) Me 1-1744 2- (4-Tol) SO_TwoHNOCHN 6-OMe H H Ph -CH (Ph) Me 1-1745 2- (4-Tol) SO_TwoHNOCHN 4-OH H H Ph -CH (Ph) Me 1-1746 2- (4-Tol) SO_TwoHNOCHN 4-F H H Ph -CH (Ph) Me 1-1747 2- (4-Tol) SO_TwoHNOCHN 4-Cl H H Ph -CH (Ph) Me 1-1748 2- (4-Tol) SO_TwoHNOCHN 4-NH_Two H H Ph -CH (Ph) Me 1-1749 2- (4-Tol) SO_TwoHNOCHN 4-NHMe H H Ph -CH (Ph) Me 1-1750 2- (4-Tol) SO_TwoHNOCHN 4-N (Me)_Two H H Ph -CH (Ph) Me 1-1751 2- (4-Tol) SO_TwoHNOCHN H H H 2-Me-Ph -CH (Ph) Me 1-1752 2- (4-Tol) SO_TwoHNOCHN H H H 3-Me-Ph -CH (Ph) Me 1-1753 2- (4-Tol) SO_TwoHNOCHN H H H 4-Me-Ph -CH (Ph) Me 1-1754 2- (4-Tol) SO_TwoHNOCHN H H H 4-MeO-Ph -CH (Ph) Me 1-1755 2- (4-Tol) SO_TwoHNOCHN H H H 4-F-Ph -CH (Ph) Me 1-1756 2- (4-Tol) SO_TwoHNOCHN H H H 4-Cl-Ph -CH (Ph) Me 1-1757 2- (4-Tol) SO_TwoHNOCHN H H H -CH (Ph) Me R^5a= 4-Me-2-MeO-Ph 1-1758 2- (4-Tol) SO_TwoHNOCHN H H H -CH (Ph) Me R^5a= 6-F-4-Me-2-MeO-Ph 1-1759 2- (4-Tol) SO_TwoHNOCHN H H H Ph -CH (4-Me-Ph) Me 1-1760 2- (4-Tol) SO_TwoHNOCHN H H H Ph -CH (4-MeO-Ph) Me 1-1761 2- (4-Tol) SO_TwoHNOCHN H H H Ph -CH (4-F-Ph) Me 1-1762 2- (4-Tol) SO_TwoHNOCHN H H H Ph -CH (4-Cl-Ph) Me 1-1763 2- (4-Tol) SO_TwoHNOCHN H H H Ph 3-Pn 1-1764 2- (4-Tol) SO_TwoHNOCHN H H H Ph -CH (cHx) Me 1-1765 2- (4-Tol) SO_TwoHNOCHN H H H Ph -CH (4-Br-Ph) Me 1-1766 2- (4-Tol) SO_TwoHNOCHN H H H Ph -CH (H_TwoNOC-Ph) Me 1-1767 2- (4-Tol) SO_TwoHNOCHN H H H Ph -CH (1-Np) Me 1-1768 2- (4-Tol) SO_TwoHNOCHN H H H 4-Me-Ph -CH (4-Br-Ph) Me 1-1769 3- (2-Tol) SO_TwoHNOCHN H H H Ph 1-Et-Pn 1-1770 3- (2-Tol) SO_TwoHNOCHN H H H Ph cHx 1-1771 3- (2-Tol) SO_TwoHNOCHN H H H Ph -CH (Ph) Me 1-1772 3- (3-Tol) SO_TwoHNOCHN H H H Ph 1-Et-Pn 1-1773 3- (3-Tol) SO_TwoHNOCHN H H H Ph cHx 1-1774 3- (3-Tol) SO_TwoHNOCHN H H H Ph -CH (Ph) Me 1-1775 3- (4-Tol) SO_TwoHNOCHN H H H Ph 1-Et-Pn 1-1776 3- (4-Tol) SO_TwoHNOCHN H H H Ph 2-Et-Hx 1-1777 3- (4-Tol) SO_TwoHNOCHN H H H Ph cHx 1-1778 3- (4-Tol) SO_TwoHNOCHN H H H Ph Bz 1-1779 3- (4-Tol) SO_TwoHNOCHN H H H Ph -CH (Ph) Me 1-1780 4- (2-Tol) SO_TwoHNOCHN H H H Ph 1-Et-Pn 1-1781 4- (2-Tol) SO_TwoHNOCHN H H H Ph cHx 1-1782 4- (2-Tol) SO_TwoHNOCHN H H H Ph -CH (Ph) Me 1-1783 4- (3-Tol) SO_TwoHNOCHN H H H Ph 1-Et-Pn 1-1785 4- (3-Tol) SO_TwoHNOCHN H H H Ph cHx 1-1786 4- (3-Tol) SO_TwoHNOCHN H H H Ph -CH (Ph) Me 1-1787 4- (4-Tol) SO_TwoHNOCHN H H H Ph 1-Et-Pn 1-1788 4- (4-Tol) SO_TwoHNOCHN H H H Ph 2-Et-Hx 1-1789 4- (4-Tol) SO_TwoHNOCHN H H H Ph cHx 1-1790 4- (4-Tol) SO_TwoHNOCHN H H H Ph Bz 1-1791 4- (4-Tol) SO_TwoHNOCHN H H H Ph -CH (Ph) Me 1-1792 2- (2-Et-Ph) SO_TwoHNOCHN H H H Ph 1-Et-Pn 1-1793 2- (2-Et-Ph) SO_TwoHNOCHN H H H Ph cHx 1-1794 2- (2-Et-Ph) SO_TwoHNOCHN H H H Ph -CH (Ph) Me 1-1795 2- (3-Et-Ph) SO_TwoHNOCHN H H H Ph 1-Et-Pn 1-1796 2- (3-Et-Ph) SO_TwoHNOCHN H H H Ph cHx 1-1797 2- (3-Et-Ph) SO_TwoHNOCHN H H H Ph -CH (Ph) Me 1-1798 2- (4-Et-Ph) SO_TwoHNOCHN H H H Ph 1-Et-Pn 1-1799 2- (4-Et-Ph) SO_TwoHNOCHN H H H Ph 2-Et-Hx 1-1800 2- (4-Et-Ph) SO_TwoHNOCHN H H H Ph cHx 1-1801 2- (4-Et-Ph) SO_TwoHNOCHN H H H Ph Bz 1-1802 2- (4-Et-Ph) SO_TwoHNOCHN H H H Ph -CH (Ph) Me 1-1803 3- (2-Et-Ph) SO_TwoHNOCHN H H H Ph cHx 1-1804 3- (3-Et-Ph) SO_TwoHNOCHN H H H Ph cHx 1-1805 3- (4-Et-Ph) SO_TwoHNOCHN H H H Ph cHx 1-1806 3- (4-Et-Ph) SO_TwoHNOCHN H H H Ph Bz 1-1807 3- (4-Et-Ph) SO_TwoHNOCHN H H H Ph -CH (Ph) Me 1-1808 4- (2-Et-Ph) SO_TwoHNOCHN H H H Ph cHx 1-1809 4- (3-Et-Ph) SO_TwoHNOCHN H H H Ph cHx 1-1810 4- (4-Et-Ph) SO_TwoHNOCHN H H H Ph cHx 1-1811 4- (4-Et-Ph) SO_TwoHNOCHN H H H Ph Bz 1-1812 4- (4-Et-Ph) SO_TwoHNOCHN H H H Ph -CH (Ph) Me 1-1813 2- (2-MeO-Ph) SO_TwoHNOCHN H H H Ph 1-Et-Pn 1-1814 2- (2-MeO-Ph) SO_TwoHNOCHN H H H Ph cHx 1-1815 2- (2-MeO-Ph) SO_TwoHNOCHN H H H Ph -CH (Ph) Me 1-1816 2- (3-MeO-Ph) SO_TwoHNOCHN H H H Ph 1-Et-Pn 1-1817 2- (3-MeO-Ph) SO_TwoHNOCHN H H H Ph cHx 1-1818 2- (3-MeO-Ph) SO_TwoHNOCHN H H H Ph -CH (Ph) Me 1-1819 2- (4-MeO-Ph) SO_TwoHNOCHN H H H Ph 1-Et-Pn 1-1820 2- (4-MeO-Ph) SO_TwoHNOCHN H H H Ph 2-Et-Hx 1-1821 2- (4-MeO-Ph) SO_TwoHNOCHN H H H Ph cHx 1-1822 2- (4-MeO-Ph) SO_TwoHNOCHN H H H Ph Bz 1-1823 2- (4-MeO-Ph) SO_TwoHNOCHN H H H Ph -CH (Ph) Me 1-1824 3- (2-MeO-Ph) SO_TwoHNOCHN H H H Ph cHx 1-1825 3- (3-MeO-Ph) SO_TwoHNOCHN H H H Ph cHx 1-1826 3- (4-MeO-Ph) SO_TwoHNOCHN H H H Ph cHx 1-1827 3- (4-MeO-Ph) SO_TwoHNOCHN H H H Ph Bz 1-1828 3- (4-MeO-Ph) SO_TwoHNOCHN H H H Ph -CH (Ph) Me 1-1829 4- (2-MeO-Ph) SO_TwoHNOCHN H H H Ph cHx 1-1830 4- (3-MeO-Ph) SO_TwoHNOCHN H H H Ph cHx 1-1831 4- (4-MeO-Ph) SO_TwoHNOCHN H H H Ph cHx 1-1832 4- (4-MeO-Ph) SO_TwoHNOCHN H H H Ph Bz 1-1833 4- (4-MeO-Ph) SO_TwoHNOCHN H H H Ph -CH (Ph) Me 1-1834 2- (2-F-Ph) SO_TwoHNOCHN H H H Ph 1-Et-Pn 1-1835 2- (2-F-Ph) SO_TwoHNOCHN H H H Ph cHx 1-1836 2- (2-F-Ph) SO_TwoHNOCHN H H H Ph -CH (Ph) Me 1-1837 2- (3-F-Ph) SO_TwoHNOCHN H H H Ph 1-Et-Pn 1-1838 2- (3-F-Ph) SO_TwoHNOCHN H H H Ph cHx 1-1839 2- (3-F-Ph) SO_TwoHNOCHN H H H Ph -CH (Ph) Me 1-1840 2- (4-F-Ph) SO_TwoHNOCHN H H H Ph 1-Et-Pn 1-1841 2- (4-F-Ph) SO_TwoHNOCHN H H H Ph 2-Et-Hx 1-1842 2- (4-F-Ph) SO_TwoHNOCHN H H H Ph cHx 1-1843 2- (4-F-Ph) SO_TwoHNOCHN H H H Ph Bz 1-1844 2- (4-F-Ph) SO_TwoHNOCHN H H H Ph -CH (Ph) Me 1-1845 3- (2-F-Ph) SO_TwoHNOCHN H H H Ph cHx 1-1846 3- (3-F-Ph) SO_TwoHNOCHN H H H Ph cHx 1-1847 3- (4-F-Ph) SO_TwoHNOCHN H H H Ph cHx 1-1848 3- (4-F-Ph) SO_TwoHNOCHN H H H Ph Bz 1-1849 3- (4-F-Ph) SO_TwoHNOCHN H H H Ph -CH (Ph) Me 1-1850 4- (2-F-Ph) SO_TwoHNOCHN H H H Ph cHx 1-1851 4- (3-F-Ph) SO_TwoHNOCHN H H H Ph cHx 1-1852 4- (4-F-Ph) SO_TwoHNOCHN H H H Ph cHx 1-1853 4- (4-F-Ph) SO_TwoHNOCHN H H H Ph Bz 1-1854 4- (4-F-Ph) SO_TwoHNOCHN H H H Ph -CH (Ph) Me 1-1855 2- (2-Cl-Ph) SO_TwoHNOCHN H H H Ph 1-Et-Pn 1-1856 2- (2-Cl-Ph) SO_TwoHNOCHN H H H Ph cHx 1-1857 2- (2-Cl-Ph) SO_TwoHNOCHN H H H Ph -CH (Ph) Me 1-1858 2- (3-Cl-Ph) SO_TwoHNOCHN H H H Ph 1-Et-Pn 1-1859 2- (3-Cl-Ph) SO_TwoHNOCHN H H H Ph cHx 1-1860 2- (3-Cl-Ph) SO_TwoHNOCHN H H H Ph -CH (Ph) Me 1-1861 2- (4-Cl-Ph) SO_TwoHNOCHN H H H Ph 1-Et-Pn 1-1862 2- (4-Cl-Ph) SO_TwoHNOCHN H H H Ph 2-Et-Hx 1-1863 2- (4-Cl-Ph) SO_TwoHNOCHN H H H Ph cHx 1-1864 2- (4-Cl-Ph) SO_TwoHNOCHN H H H Ph Bz 1-1865 2- (4-Cl-Ph) SO_TwoHNOCHN H H H Ph -CH (Ph) Me 1-1866 3- (2-Cl-Ph) SO_TwoHNOCHN H H H Ph cHx 1-1867 3- (3-Cl-Ph) SO_TwoHNOCHN H H H Ph cHx 1-1868 3- (4-Cl-Ph) SO_TwoHNOCHN H H H Ph cHx 1-1869 3- (4-Cl-Ph) SO_TwoHNOCHN H H H Ph Bz 1-1870 3- (4-Cl-Ph) SO_TwoHNOCHN H H H Ph -CH (Ph) Me 1-1871 4- (2-Cl-Ph) SO_TwoHNOCHN H H H Ph cHx 1-1872 4- (3-Cl-Ph) SO_TwoHNOCHN H H H Ph cHx 1-1873 4- (4-Cl-Ph) SO_TwoHNOCHN H H H Ph cHx 1-1874 4- (4-Cl-Ph) SO_TwoHNOCHN H H H Ph Bz 1-1875 4- (4-Cl-Ph) SO_TwoHNOCHN H H H Ph -CH (Ph) Me 1-1876 3-Tz 6-F H H Ph -CH (Ph) Me  .

[0088]

[Table 2] R ¹ R ² R ³ R ⁴ R ^5b R ⁶ 2-1 2- (2-MeSO ₂ -Ph) HHH 2-Inde 1-Et-Pn 2-2 2- (2-MeSO ₂ -Ph) HHH 2- (5-Me-Inde) cHx 2-3 2 -(2-MeSO ₂ -Ph) HHH 2-Inde cHx 2-4 2- (2-MeSO ₂ -Ph) HHH 2-Inde -CH (Ph) Me 2-5 2- (2-MeSO ₂ -Ph) HHH 2-Inde -CH (4-Br-Ph) Me 2-6 2- (2-MeSO ₂ -Ph) HHH 2-Inde -CH (1-Np) Me 2-7 4- (2-MeSO _2- Ph) HHH 2-Inde 1-Et-Pn 2-8 4- (2-MeSO ₂ -Ph) HHH 2- (5-Me-Inde) cHx 2-9 4- (2-MeSO ₂ -Ph) HHH 2 -Inde cHx 2-10 4- (2-MeSO ₂ -Ph) HHH 2-Inde -CH (Ph) Me 2-11 4- (2-MeSO ₂ -Ph) HHH 2-Inde -CH (4-Br- Ph) Me 2-12 4- (2-MeSO ₂ -Ph) HHH 2-Inde -CH (1-Np) Me 2-13 2- (2-EtSO ₂ -Ph) HHH 2-Inde cHx 2-14 4 -(4-EtSO ₂ -Ph) HHH 2-Inde cHx 2-15 3-Tz HHH 2-Inde 1-Et-Pn 2-16 3-Tz HHH 2- (5-Me-Inde) cHx 2-17 3 -Tz HHH 2-Inde cHx 2-18 3-Tz HHH 2-Inde -CH (Ph) Me 2-19 3-Tz HHH 2-Inde -CH (4-Br-Ph) Me 2-20 3-Tz HHH 2-Inde -CH (1-Np) Me 2-21 4-Tz HHH 2-Inde 1-Et-Pn 2-22 4-Tz HHH 2- (5-Me-Inde) cHx 2-23 4-Tz HHH 2-Inde cHx 2-24 4-Tz HHH 2-Inde -CH (Ph) Me 2-25 4-Tz HHH 2-Inde -CH (4-Br-Ph) Me 2-26 4-Tz HHH 2-Inde -CH (1-Np) Me 2-27 3- (2-Tol) SO ₂ HNOC HHH 2-Inde -CH (Ph) Me 2- 28 3- (3-Tol) SO ₂ HNOC HHH 2-Inde -CH (Ph) Me 2-29 3- (4-Tol) SO ₂ HNOC HHH 2-Inde 1-Et-Pn 2-30 3- (4 -Tol) SO ₂ HNOC HHH 2-Inde cHx 2-31 3- (4-Tol) SO ₂ HNOC HHH 2-Inde -CH (Ph) Me 2-32 4- (4-Tol) SO ₂ HNOC HHH 2- Inde -CH (Ph) Me 2-33 2- [2- (2-Tol) Ph] SO ₂ HNOC HHH 2-Inde -CH (Ph) Me 2-34 3- [2- (2-Tol) Ph] SO ₂ HNOC HHH 2-Inde 1-Et-Pn 2-35 3- [2- (2-Tol) Ph] SO ₂ HNOC HHH 2-Inde cHx 2-36 3- [2- (2-Tol) Ph] SO ₂ HNOC HHH 2-Inde -CH (Ph) Me 2-37 3- [2- (3-Tol) Ph] SO ₂ HNOC HHH 2-Inde -CH (Ph) Me 2-38 3- [2- ( 4-Tol) Ph] SO ₂ HNOC HHH 2-Inde -CH (Ph) Me 2-39 3- [4- (2-Tol) Ph] SO ₂ HNOC HHH 2-Inde -CH (Ph) Me 2-40 3- [4- (3-Tol) Ph] SO ₂ HNOC HHH 2-Inde -CH (Ph) Me 2-41 3- [4- (4-Tol) Ph] SO ₂ HNOC HHH 2-Inde -CH ( Ph) Me 2-42 4- [2- (2-Tol) Ph] SO ₂ HNOC HHH 2-Inde -CH (Ph) Me 2-43 4- [2- (3-Tol) Ph] SO ₂ HNOC HHH 2-Inde -CH (Ph) Me 2-44 4- [2- (4-Tol) Ph] SO ₂ HNOC HHH 2-Inde -CH (Ph) Me 2-45 2-MeSO ₂ HHH 2-Inde 1- Et-Pn 2-46 2-MeSO ₂ HHH 2- (5-Me-Inde) cHx 2-47 2-MeSO ₂ HHH 2-Inde cHx 2-48 2-MeSO ₂ HHH 2-Inde -CH (Ph) Me 2-49 2-MeSO ₂ HHH 2-Inde -CH (4-Br-Ph) Me 2-50 2-M eSO ₂ HHH 2-Inde -CH (1-Np) Me 2-51 3-MeSO ₂ HHH 2-Inde 1-Et-Pn 2-52 3-MeSO ₂ HHH 2-Inde cHx 2-53 3-MeSO ₂ HHH 2-Inde -CH (Ph) Me 2-54 4-MeSO ₂ HHH 2-Inde 1-Et-Pn 2-55 4-MeSO ₂ HHH 2-Inde cHx 2-56 4-MeSO ₂ HHH 2-Inde -CH (Ph) Me 2-57 4-MeSO ₂ HHH 2-Inde -CH (4-Br-Ph) Me 2-58 4-MeSO ₂ HHH 2-Inde -CH (1-Np) Me 2-59 2-EtSO ₂ HHH 2-Inde 1-Et-Pn 2-60 2-EtSO ₂ HHH 2- (5-Me-Inde) cHx 2-61 2-EtSO ₂ HHH 2-Inde cHx 2-62 2-EtSO ₂ HHH 2- Inde -CH (Ph) Me 2-63 2-EtSO ₂ HHH 2-Inde -CH (4-Br-Ph) Me 2-64 2-EtSO ₂ HHH 2-Inde -CH (1-Np) Me 2-65 3-EtSO ₂ HHH 2-Inde 1-Et-Pn 2-66 3-EtSO ₂ HHH 2-Inde cHx 2-67 3-EtSO ₂ HHH 2-Inde -CH (Ph) Me 2-68 4-EtSO ₂ HHH 2-Inde 1-Et-Pn 2-69 4-EtSO ₂ HHH 2- (5-Me-Inde) cHx 2-70 4-EtSO ₂ HHH 2-Inde cHx 2-71 4-EtSO ₂ HHH 2-Inde- CH (Ph) Me 2-72 4-EtSO ₂ HHH 2-Inde -CH (4-Br-Ph) Me 2-73 4-EtSO ₂ HHH 2-Inde -CH (1-Np) Me 2-74 2- PrSO ₂ HHH 2-Inde -CH (Ph) Me 2-75 4-PrSO ₂ HHH 2-Inde -CH (Ph) Me 2-76 2-BuSO ₂ HHH 2-Inde 1-Et-Pn 2-77 2- BuSO ₂ HHH 2- (5-Me-Inde) cHx 2-78 2-BuSO ₂ HHH 2-Inde cHx 2-79 2-BuSO ₂ H HH 2-Inde -CH (Ph) Me 2-80 4-BuSO ₂ HHH 2-Inde -CH (4-Br-Ph) Me 2-81 4-BuSO ₂ HHH 2-Inde -CH (1-Np) Me 2-82 3-BuSO ₂ HHH 2-Inde 1-Et-Pn 2-83 3-BuSO ₂ HHH 2-Inde cHx 2-84 3-BuSO ₂ HHH 2-Inde -CH (Ph) Me 2-85 4- BuSO ₂ HHH 2-Inde 1-Et-Pn 2-86 4-BuSO ₂ HHH 2-Inde cHx 2-87 4-BuSO ₂ HHH 2-Inde -CH (Ph) Me 2-88 2-PhSO ₂ HHH 2- Inde 1-Et-Pn 2-89 2-PhSO ₂ HHH 2-Inde cHx 2-90 2-PhSO ₂ HHH 2-Inde -CH (Ph) Me 2-91 3-PhSO ₂ HHH 2-Inde cHx 2-92 4-PhSO ₂ HHH 2-Inde cHx 2-93 2- (2-Tol) SO ₂ HNOCHN HHH 2-Inde -CH (Ph) Me 2-94 2- (3-Tol) SO ₂ HNOCHN HHH 2-Inde- CH (Ph) Me 2-95 2- (4-Tol) SO ₂ HNOCHN HHH 2-Inde 1-Et-Pn 2-96 2- (4-Tol) SO ₂ HNOCHN HHH 2-Inde cHx 2-97 2- (4-Tol) SO ₂ HNOCHN HHH 2-Inde -CH (Ph) Me 2-98 2- (4-Tol) SO ₂ HNOCHN HHH 2- (5-Me-Inde) -CH (Ph) Me 2-99 2- (4-Tol) SO ₂ HNOCHN HHH 2-Inde -CH (4-Br-Ph) Me 2-100 2- (4-Tol) SO ₂ HNOCHN HHH 2-Inde -CH (1-Np) Me 2 -101 3- (4-Tol) SO 2 HNOCHN HHH 2-Inde -CH (Ph) Me 2-102 4- (4-Tol) SO 2 HNOCHN HHH 2-Inde -CH (Ph) Me 2-103 2- MeSO HHH 2-Inde cHx 2-104 2-MeSO HHH 2-Inde -CH (Ph) Me 2-105 2- (2-Me SO ₂ -Ph) HHH 3-Inde 1-Et-Pn 2-106 2- (2-MeSO ₂ -Ph) HHH 3- (5-Me-Inde) cHx 2-107 2- (2-MeSO ₂ -Ph ) HHH 3-Inde cHx 2-108 2- (2-MeSO ₂ -Ph) HHH 3-Inde -CH (Ph) Me 2-109 2- (2-MeSO ₂ -Ph) HHH 3-Inde -CH (4 -Br-Ph) Me 2-110 2- (2-MeSO ₂ -Ph) HHH 3-Inde -CH (1-Np) Me 2-111 4- (2-MeSO ₂ -Ph) HHH 3-Inde 1- Et-Pn 2-112 4- (2-MeSO ₂ -Ph) HHH 3- (5-Me-Inde) cHx 2-113 4- (2-MeSO ₂ -Ph) HHH 3-Inde cHx 2-114 4- (2-MeSO ₂ -Ph) HHH 3-Inde -CH (Ph) Me 2-115 4- (2-MeSO ₂ -Ph) HHH 3-Inde -CH (4-Br-Ph) Me 2-116 4- (2-MeSO ₂ -Ph) HHH 3-Inde -CH (1-Np) Me 2-117 2- (2-EtSO ₂ -Ph) HHH 3-Inde cHx 2-118 4- (4-EtSO ₂ -Ph ) HHH 3-Inde cHx 2-119 3-Tz HHH 3-Inde 1-Et-Pn 2-120 3-Tz HHH 3- (5-Me-Inde) cHx 2-121 3-Tz HHH 3-Inde cHx 2 -122 3-Tz HHH 3-Inde -CH (Ph) Me 2-123 3-Tz HHH 3-Inde -CH (4-Br-Ph) Me 2-124 3-Tz HHH 3-Inde -CH (1- Np) Me 2-125 4-Tz HHH 3-Inde 1-Et-Pn 2-126 4-Tz HHH 3- (5-Me-Inde) cHx 2-127 4-Tz HHH 3-Inde cHx 2-128 4 -Tz HHH 3-Inde -CH (Ph) Me 2-129 4-Tz HHH 3-Inde -CH (4-Br-Ph) Me 2-130 4-Tz HHH 3-Inde -CH (1-Np) Me 2-131 3- (2-Tol) SO ₂ HNOC HHH 3-Inde -CH (Ph) Me 2-132 3- (3-Tol) SO ₂ HNOC HHH 3-Inde -CH (Ph) Me 2-133 3- (4-Tol) SO ₂ HNOC HHH 3-Inde 1-Et-Pn 2-134 3- (4-Tol) SO ₂ HNOC HHH 3-Inde cHx 2-135 3- (4-Tol) SO ₂ HNOC HHH 3-Inde -CH (Ph) Me 2-136 4 -(4-Tol) SO ₂ HNOC HHH 3-Inde -CH (Ph) Me 2-137 2- [2- (2-Tol) Ph] SO ₂ HNOC HHH 3-Inde -CH (Ph) Me 2-138 3- [2- (2-Tol) Ph] SO ₂ HNOC HHH 3-Inde 1-Et-Pn 2-139 3- [2- (2-Tol) Ph] SO ₂ HNOC HHH 3-Inde cHx 2-140 3- [2- (2-Tol) Ph] SO ₂ HNOC HHH 3-Inde -CH (Ph) Me 2-141 3- [2- (3-Tol) Ph] SO ₂ HNOC HHH 3-Inde -CH ( Ph) Me 2-142 3- [2- (4-Tol) Ph] SO ₂ HNOC HHH 3-Inde -CH (Ph) Me 2-143 3- [4- (2-Tol) Ph] SO ₂ HNOC HHH 3-Inde -CH (Ph) Me 2-144 3- [4- (3-Tol) Ph] SO ₂ HNOC HHH 3-Inde -CH (Ph) Me 2-145 3- [4- (4-Tol) Ph] SO ₂ HNOC HHH 3-Inde -CH (Ph) Me 2-146 4- [2- (2-Tol) Ph] SO ₂ HNOC HHH 3-Inde -CH (Ph) Me 2-147 4- [2 -(3-Tol) Ph] SO ₂ HNOC HHH 3-Inde -CH (Ph) Me 2-148 4- [2- (4-Tol) Ph] SO ₂ HNOC HHH 3-Inde -CH (Ph) Me 2 -149 2-MeSO ₂ HHH 3-Inde 1-Et-Pn 2-150 2-MeSO ₂ HHH 3- (5-Me-Inde) cHx 2-151 2-MeSO ₂ HHH 3-Inde cHx 2-152 2- MeSO ₂ HHH 3-Inde -CH (Ph) Me 2-15 3 2-MeSO ₂ HHH 3-Inde -CH (4-Br-Ph) Me 2-154 2-MeSO ₂ HHH 3-Inde -CH (1-Np) Me 2-155 3-MeSO ₂ HHH 3-Inde 1 -Et-Pn 2-156 3-MeSO ₂ HHH 3-Inde cHx 2-157 3-MeSO ₂ HHH 3-Inde -CH (Ph) Me 2-158 4-MeSO ₂ HHH 3-Inde 1-Et-Pn 2 -159 4-MeSO ₂ HHH 3-Inde cHx 2-160 4-MeSO ₂ HHH 3-Inde -CH (Ph) Me 2-161 2-MeSO ₂ HHH 3-Inde -CH (4-Br-Ph) Me 2 -162 2-MeSO ₂ HHH 3-Inde -CH (1-Np) Me 2-163 2-EtSO ₂ HHH 3-Inde 1-Et-Pn 2-164 2-EtSO ₂ HHH 3- (5-Me-Inde ) cHx 2-165 2-EtSO ₂ HHH 3-Inde cHx 2-166 2-EtSO ₂ HHH 3-Inde -CH (Ph) Me 2-167 2-EtSO ₂ HHH 3-Inde -CH (4-Br-Ph ) Me 2-168 2-EtSO ₂ HHH 3-Inde -CH (1-Np) Me 2-169 3-EtSO ₂ HHH 3-Inde 1-Et-Pn 2-170 3-EtSO ₂ HHH 3-Inde cHx 2 -171 3-EtSO ₂ HHH 3-Inde -CH (Ph) Me 2-172 4-EtSO ₂ HHH 3-Inde 1-Et-Pn 2-173 4-EtSO ₂ HHH 3- (5-Me-Inde) cHx 2-174 4-EtSO ₂ HHH 3-Inde cHx 2-175 4-EtSO ₂ HHH 3-Inde -CH (Ph) Me 2-176 4-EtSO ₂ HHH 3-Inde -CH (4-Br-Ph) Me 2-177 4-EtSO ₂ HHH 3-Inde -CH (1-Np) Me 2-178 2-PrSO ₂ HHH 3-Inde -CH (Ph) Me 2-179 4-PrSO ₂ HHH 3-Inde -CH ( Ph) Me 2-180 2-BuSO ₂ HHH 3-Inde 1-Et-Pn 2-181 2- BuSO ₂ HHH 3- (5-Me-Inde) cHx 2-182 2-BuSO ₂ HHH 3-Inde cHx 2-183 2-BuSO ₂ HHH 3-Inde -CH (Ph) Me 2-184 2-BuSO ₂ HHH 3-Inde -CH (4-Br-Ph) Me 2-185 2-BuSO ₂ HHH 3-Inde -CH (1-Np) Me 2-186 3-BuSO ₂ HHH 3-Inde 1-Et-Pn 2- 187 3-BuSO ₂ HHH 3-Inde cHx 2-188 3-BuSO ₂ HHH 3-Inde -CH (Ph) Me 2-189 4-BuSO ₂ HHH 3-Inde 1-Et-Pn 2-190 4-BuSO ₂ HHH 3-Inde cHx 2-191 4-BuSO ₂ HHH 3-Inde -CH (Ph) Me 2-192 2-PhSO ₂ HHH 3-Inde 1-Et-Pn 2-193 2-PhSO ₂ HHH 3-Inde cHx 2-194 2-PhSO ₂ HHH 3-Inde -CH (Ph) Me 2-195 3-PhSO ₂ HHH 3-Inde cHx 2-196 4-PhSO ₂ HHH 3-Inde cHx 2-197 2- (2-Tol ) SO ₂ HNOCHN HHH 3-Inde -CH (Ph) Me 2-198 2- (3-Tol) SO ₂ HNOCHN HHH 3-Inde -CH (Ph) Me 2-199 2- (4-Tol) SO ₂ HNOCHN HHH 3-Inde 1-Et-Pn 2-200 2- (4-Tol) SO ₂ HNOCHN HHH 3-Inde cHx 2-201 2- (4-Tol) SO ₂ HNOCHN HHH 3-Inde -CH (Ph) Me 2-202 2- (4-Tol) SO ₂ HNOCHN HHH 3- (5-Me-Inde) -CH (Ph) Me 2-203 2- (4-Tol) SO ₂ HNOCHN HHH 3-Inde -CH (4 -Br-Ph) Me 2-204 2- (4-Tol) SO ₂ HNOCHN HHH 3-Inde -CH (1-Np) Me 2-205 3- (4-Tol) SO ₂ HNOCHN HHH 3-Inde -CH (Ph) Me 2-206 4- (4-Tol) SO ₂ HNOCHN H HH 3-Inde -CH (Ph) Me 2-207 2-MeSO HHH 3-Inde cHx 2-208 2-MeSO HHH 3-Inde -CH (Ph) Me 2-209 2- (2-MeSO ₂ -Ph) HHH 1-Np 1-Et-Pn 2-210 2- (2-MeSO ₂ -Ph) HHH 1-Np 2-Et-Hx 2-211 2- (2-MeSO ₂ -Ph) HHH 1- (5- Me-Np) cHx 2-212 2- (2-MeSO ₂ -Ph) HHH 1-Np cHx 2-213 2- (2-MeSO ₂ -Ph) HHH 1-Np Bz 2-214 2- (2-MeSO ₂ -Ph) HHH 1-Np -CH (Ph) Me 2-215 2- (2-MeSO ₂ -Ph) HHH 1-Np -CH (4-Br-Ph) Me 2-216 2- (2-MeSO ₂ -Ph) HHH 1-Np -CH (1-Np) Me 2-217 2- (3-MeSO ₂ -Ph) HHH 1-Np cHx 2-218 2- (4-MeSO ₂ -Ph) HHH 1- Np 1-Et-Pn 2-219 2- (4-MeSO ₂ -Ph) HHH 1-Np cHx 2-220 2- (4-MeSO ₂ -Ph) HHH 1-Np -CH (Ph) Me 2-221 3- (2-MeSO ₂ -Ph) HHH 1-Np cHx 2-222 3- (4-MeSO ₂ -Ph) HHH 1-Np cHx 2-223 4- (2-MeSO ₂ -Ph) HHH 1-Np 1-Et-Pn 2-224 4- (2-MeSO ₂ -Ph) HHH 1-Np 2-Et-Hx 2-225 4- (2-MeSO ₂ -Ph) HHH 1-Np cHx 2-226 4- (2-MeSO ₂ -Ph) HHH 1-Np Bz 2-227 4- (2-MeSO ₂ -Ph) HHH 1-Np -CH (Ph) Me 2-228 4- (3-MeSO ₂ -Ph) HHH 1-Np cHx 2-229 4- (4-MeSO ₂ -Ph) HHH 1-Np 1-Et-Pn 2-230 4- (4-MeSO ₂ -Ph) HHH 1-Np cHx 2-231 4- ( 4-MeSO ₂ -Ph) HHH 1-Np -CH (Ph) Me 2-232 2- (2-EtSO ₂ -Ph) HHH 1-Np 1-Et-Pn 2-233 2- (2-EtSO ₂ -Ph) HHH 1-Np cHx 2-234 2- (2-EtSO ₂ -Ph) HHH 1-Np -CH ( Ph) Me 2-235 4- (4-EtSO ₂ -Ph) HHH 1- (5-Me-Np) cHx 2-236 4- (4-EtSO ₂ -Ph) HHH 1-Np cHx 2-237 2- Tz HHH 1-Np 1-Et-Pn 2-238 2-Tz HHH 1-Np cHx 2-239 2-Tz HHH 1-Np -CH (Ph) Me 2-240 2-Tz HHH 1-Np -CH ( 4-Br-Ph) Me 2-241 2-Tz HHH 1-Np -CH (1-Np) Me 2-242 3-Tz HHH 1-Np 1-Et-Pn 2-243 3-Tz HHH 1-Np 2-Et-Hx 2-244 3-Tz HHH 1- (5-Me-Np) cHx 2-245 3-Tz HHH 1-Np cHx 2-246 3-Tz HHH 1-Np Bz 2-247 3-Tz HHH 1-Np -CH (Ph) Me 2-248 3-Tz HHH 1-Np -CH (4-Br-Ph) Me 2-249 3-Tz HHH 1-Np -CH (1-Np) Me 2- 250 4-Tz HHH 1-Np 1-Et-Pn 2-251 4-Tz HHH 1-Np 2-Et-Hx 2-252 4-Tz HHH 1- (5-Me-Np) cHx 2-253 4- Tz HHH 1-Np cHx 2-254 4-Tz HHH 1-Np Bz 2-255 4-Tz HHH 1-Np -CH (Ph) Me 2-256 4-Tz HHH 1-Np -CH (4-Br- Ph) Me 2-257 4-Tz HHH 1-Np -CH (1-Np) Me 2-258 2- (4-Tol) SO ₂ HNOC HHH 1-Np -CH (Ph) Me 2-259 3- ( 2-Tol) SO ₂ HNOC HHH 1-Np -CH (Ph) Me 2-260 3- (3-Tol) SO ₂ HNOC HHH 1-Np -CH (Ph) Me 2-261 3- (4-Tol) SO ₂ HNOC HHH 1-Np 1-Et-Pn 2-262 3- (4-Tol) SO ₂ HNOC H HH 1-Np cHx 2-263 3- (4-Tol) SO ₂ HNOC HHH 1-Np -CH (Ph) Me 2-264 4- (4-Tol) SO ₂ HNOC HHH 1-Np -CH (Ph) Me 2-265 2- [2- (2-Tol) Ph] SO ₂ HNOC HHH 1-Np -CH (Ph) Me 2-266 3- [2- (2-Tol) Ph] SO ₂ HNOC HHH 1- Np 1-Et-Pn 2-267 3- [2- (2-Tol) Ph] SO ₂ HNOC HHH 1-Np cHx 2-268 3- [2- (2-Tol) Ph] SO ₂ HNOC HHH 1- Np -CH (Ph) Me 2-269 3- [2- (3-Tol) Ph] SO ₂ HNOC HHH 1-Np 1-Et-Pn 2-270 3- [2- (3-Tol) Ph] SO ₂ HNOC HHH 1-Np cHx 2-271 3- [2- (3-Tol) Ph] SO ₂ HNOC HHH 1-Np -CH (Ph) Me 2-272 3- [2- (4-Tol) Ph] SO ₂ HNOC HHH 1-Np 1-Et-Pn 2-273 3- [2- (4-Tol) Ph] SO ₂ HNOC HHH 1-Np cHx 2-274 3- [2- (4-Tol) Ph] SO ₂ HNOC HHH 1-Np -CH (Ph) Me 2-275 3- [3- (2-Tol) Ph] SO ₂ HNOC HHH 1-Np -CH (Ph) Me 2-276 3- [3- ( 3-Tol) Ph] SO ₂ HNOC HHH 1-Np -CH (Ph) Me 2-277 3- [3- (4-Tol) Ph] SO ₂ HNOC HHH 1-Np -CH (Ph) Me 2-278 3- [4- (2-Tol) Ph] SO ₂ HNOC HHH 1-Np -CH (Ph) Me 2-279 3- [4- (3-Tol) Ph] SO ₂ HNOC HHH 1-Np -CH ( Ph) Me 2-280 3- [4- (4-Tol) Ph] SO ₂ HNOC HHH 1-Np -CH (Ph) Me 2-281 4- [2- (2-Tol) Ph] SO ₂ HNOC HHH 1-Np -CH (Ph) Me 2-282 4- [2- (3-Tol) Ph] SO ₂ HNOC HHH 1-Np -CH (Ph) Me 2-283 4- [2- (4-Tol) Ph] SO ₂ HNOC HHH 1-Np -CH (Ph) Me 2-284 4- [2- (2-Et-Ph) Ph] SO ₂ HNOC HHH 1-Np -CH (Ph) Me 2-285 4- [2- (2-MeO-Ph) Ph] SO ₂ HNOC HHH 1-Np -CH (Ph) Me 2-286 4- [2- (2-F-Ph) Ph] SO ₂ HNOC HHH 1-Np -CH (Ph ) Me 2-287 2-MeSO ₂ HHH 1-Np 1-Et-Pn 2-288 2-MeSO ₂ HHH 1-Np 2-Et-Hx 2-289 2-MeSO ₂ HHH 1- (5-Me-Np ) cHx 2-290 2-MeSO ₂ HHH 1-Np cHx 2-291 2-MeSO ₂ HHH 1-Np Bz 2-292 2-MeSO ₂ HHH 1-Np -CH (Ph) Me 2-293 2-MeSO ₂ HHH 1-Np -CH (4-Br-Ph) Me 2-294 2-MeSO ₂ HHH 1-Np -CH (1-Np) Me 2-295 3-MeSO ₂ HHH 1-Np 1-Et-Pn 2 -296 3-MeSO ₂ HHH 1-Np cHx 2-297 3-MeSO ₂ HHH 1-Np -CH (Ph) Me 2-298 4-MeSO ₂ HHH 1-Np 1-Et-Pn 2-299 4-MeSO ₂ HHH 1-Np 2-Et-Hx 2-300 4-MeSO ₂ HHH 1-Np cHx 2-301 4-MeSO ₂ HHH 1-Np Bz 2-302 4-MeSO ₂ HHH 1-Np -CH (Ph) Me 2-303 4-MeSO ₂ HHH 1-Np -CH (4-Br-Ph) Me 2-304 4-MeSO ₂ HHH 1-Np -CH (1-Np) Me 2-305 2-EtSO ₂ HHH 1 -Np 1-Et-Pn 2-306 2-EtSO ₂ HHH 1-Np 2-Et-Hx 2-307 2-EtSO ₂ HHH 1- (5-Me-Np) cHx 2-308 2-EtSO ₂ HHH 1 -Np cHx 2-309 2-EtSO ₂ HHH 1-Np Bz 2-310 2-EtSO ₂ HHH 1-Np -CH (Ph) Me 2-311 2-EtSO ₂ HHH 1-Np -CH (4-Br- Ph) Me 2-312 2-EtSO ₂ HHH 1-Np -CH (1-Np) Me 2-313 3-EtSO ₂ HHH 1-Np 1-Et-Pn 2-314 3-EtSO ₂ HHH 1-Np cHx 2-315 3-EtSO ₂ HHH 1-Np -CH (Ph) Me 2-316 4-EtSO ₂ HHH 1-Np 1-Et-Pn 2-317 4-EtSO ₂ HHH 1-Np 2-Et-Hx 2-318 4-EtSO ₂ HHH 1- (5-Me-Np) cHx 2-319 4-EtSO ₂ HHH 1-Np cHx 2-320 4-EtSO ₂ HHH 1-Np -CH (Ph) Me 2-321 4-EtSO ₂ HHH 1- Np -CH (4-Br-Ph) Me 2-322 4-EtSO ₂ HHH 1-Np -CH (1-Np) Me 2-323 2-PrSO ₂ HHH 1-Np -CH (Ph) Me 2-324 4-PrSO ₂ HHH 1-Np -CH (Ph) Me 2-325 2-BuSO ₂ HHH 1-Np 1-Et-Pn 2-326 2-BuSO ₂ HHH 1- (5-Me-Np) cHx 2- 327 2-BuSO ₂ HHH 1-Np cHx 2-328 2-BuSO ₂ HHH 1-Np -CH (Ph) Me 2-329 2-BuSO ₂ HHH 1-Np -CH (4-Br-Ph) Me 2- 330 2-BuSO ₂ HHH 1-Np -CH (1-Np) Me 2-331 3-BuSO ₂ HHH 1-Np 1-Et-Pn 2-332 3-BuSO ₂ HHH 1-Np cHx 2-333 3- BuSO ₂ HHH 1-Np -CH (Ph) Me 2-334 4-BuSO ₂ HHH 1-Np 1-Et-Pn 2-335 4-BuSO ₂ HHH 1-Np cHx 2-336 4-BuSO ₂ HHH 1- Np -CH (Ph) Me 2-337 2-PhSO ₂ HHH 1-Np 1-Et-Pn 2-338 2-PhSO ₂ HHH 1-Np cHx 2-339 2-PhSO ₂ HHH 1-Np -CH (Ph ) Me 2-340 3-PhSO ₂ HHH 1-Np cHx 2-341 4-PhSO ₂ HHH 1-Np cHx 2-342 2- (2-Tol) SO ₂ HNOCHN HHH 1-Np 1-Et-Pn 2-343 2- (2-Tol) SO ₂ HNOCHN HHH 1-Np cHx 2-344 2- (2-Tol) SO ₂ HNOCHN HHH 1-Np -CH (Ph) Me 2 -345 2- (3-Tol) SO ₂ HNOCHN HHH 1-Np 1-Et-Pn 2-346 2- (3-Tol) SO ₂ HNOCHN HHH 1-Np cHx 2-347 2- (3-Tol) SO ₂ HNOCHN HHH 1-Np -CH (Ph) Me 2-348 2- (4-Tol) SO ₂ HNOCHN HHH 1-Np 1-Et-Pn 2-349 2- (4-Tol) SO ₂ HNOCHN HHH 1- Np 2-Et-Hx 2-350 2- (4-Tol) SO ₂ HNOCHN HHH 1-Np cHx 2-351 2- (4-Tol) SO ₂ HNOCHN HHH 1-Np Bz 2-352 2- (4- Tol) SO ₂ HNOCHN HHH 1-Np -CH (Ph) Me 2-353 2- (4-Tol) SO ₂ HNOCHN HHH 1- (5-Me-Np) -CH (Ph) Me 2-354 2- ( 4-Tol) SO ₂ HNOCHN HHH 1-Np -CH (4-Br-Ph) Me 2-355 2- (4-Tol) SO ₂ HNOCHN HHH 1-Np -CH (1-Np) Me 2-356 3 -(4-Tol) SO ₂ HNOCHN HHH 1-Np -CH (Ph) Me 2-357 4- (4-Tol) SO ₂ HNOCHN HHH 1-Np -CH (Ph) Me 2-358 2- (4- Et-Ph) SO ₂ HNOCHN HHH 1-Np -CH (Ph) Me 2-359 2- (4-MeO-Ph) SO ₂ HNOCHN HHH 1-Np -CH (Ph) Me 2-360 2- (4- F-Ph) SO ₂ HNOCHN HHH 1-Np -CH (Ph) Me 2-361 2- (4-Cl-Ph) SO ₂ HNOCHN HHH 1-Np -CH (Ph) Me 2-362 2-MeSO HHH 1 -Np -CH (Ph) Me 2-363 2-EtSO HHH 1-Np -CH (Ph) Me 2-364 3-MeSO HHH 1-Np -CH (Ph) Me 2-365 4-MeSO HHH 1-Np -CH (Ph) Me 2-366 2- (2-MeSO ₂ -Ph) HHH 2-Np 1-Et-Pn 2-367 2- (2-MeSO ₂ -Ph) HHH 2-Np 2-Et-Hx 2- 368 2- (2-MeSO ₂ -Ph) HHH 2- (5-Me-Np) cHx 2-369 2- (2-MeSO ₂ -Ph) HHH 2-Np cHx 2-370 2- (2-MeSO ₂ -Ph) HHH 2-Np Bz 2-371 2- (2-MeSO ₂ -Ph) HHH 2-Np -CH (Ph) Me 2-372 2- (2-MeSO ₂ -Ph) HHH 2-Np -CH (4-Br-Ph) Me 2-373 2- (2-MeSO ₂ -Ph) HHH 2-Np -CH (1-Np) Me 2-374 2- (3-MeSO ₂ -Ph) HHH 2-Np cHx 2-375 2- (4-MeSO ₂ -Ph) HHH 2-Np 1-Et-Pn 2-376 2- (4-MeSO ₂ -Ph) HHH 2-Np cHx 2-377 2- (4-MeSO ₂ -Ph) HHH 2-Np -CH (Ph) Me 2-378 3- (2-MeSO ₂ -Ph) HHH 2-Np cHx 2-379 3- (4-MeSO ₂ -Ph) HHH 2-Np cHx 2-380 4- (2-MeSO ₂ -Ph) HHH 2-Np 1-Et-Pn 2-381 4- (2-MeSO ₂ -Ph) HHH 2-Np 2-Et-Hx 2-382 4- ( 2-MeSO ₂ -Ph) HHH 2-Np cHx 2-383 4- (2-MeSO ₂ -Ph) HHH 2-Np Bz 2-384 4- (2-MeSO ₂ -Ph) HHH 2-Np -CH ( Ph) Me 2-385 4- (3-MeSO ₂ -Ph) HHH 2-Np cHx 2-386 4- (4-MeSO ₂ -Ph) HHH 2-Np 1-Et-Pn 2-387 4- (4 -MeSO ₂ -Ph) HHH 2-Np cHx 2-388 4- (4-MeSO ₂ -Ph) HHH 2-Np -CH (Ph) Me 2-389 2- (2-EtSO ₂ -Ph) HHH 2- Np 1-Et-Pn 2-390 2- (2-EtSO ₂ -Ph) HHH 2-Np cHx 2-391 2- (2-EtSO ₂ -Ph) HHH 2-Np -CH (Ph) Me 2-392 4- (4-EtSO ₂ -Ph) HHH 2- (5-Me-Np) cHx 2-393 4- (4-EtSO ₂ -Ph) HHH 2-Np cHx 2-394 2-Tz HHH 2-Np 1-Et-Pn 2-395 2-Tz HHH 2-Np cHx 2-396 2-Tz HHH 2-Np -CH (Ph) Me 2-398 2-Tz HHH 2-Np -CH (1-Np) Me 2-399 3-Tz HHH 2-Np 1-Et-Pn 2-400 3-Tz HHH 2-Np 2-Et-Hx 2-401 3- Tz HHH 2- (5-Me-Np) cHx 2-402 3-Tz HHH 2-Np cHx 2-403 3-Tz HHH 2-Np Bz 2-404 3-Tz HHH 2-Np -CH (Ph) Me 2-405 3-Tz HHH 2-Np- -CH (4-Br-Ph) Me 2-406 3-Tz HHH 2-Np -CH (1-Np) Me 2-407 4-Tz HHH 2-Np 1 -Et-Pn 2-408 4-Tz HHH 2-Np 2-Et-Hx 2-409 4-Tz HHH 2- (5-Me-Np) cHx 2-410 4-Tz HHH 2-Np cHx 2-411 4-Tz HHH 2-Np Bz 2-412 4-Tz HHH 2-Np -CH (Ph) Me 2-413 4-Tz HHH 2-Np -CH (4-Br-Ph) Me 2-414 4-Tz HHH 2-Np -CH (1-Np) Me 2-415 2- (4-Tol) SO ₂ HNOC HHH 2-Np -CH (Ph) Me 2-416 3- (2-Tol) SO ₂ HNOC HHH 2 -Np -CH (Ph) Me 2-417 3- (3-Tol) SO ₂ HNOC HHH 2-Np -CH (Ph) Me 2-418 3- (4-Tol) SO ₂ HNOC HHH 2-Np 1- Et-Pn 2-419 3- (4-Tol) SO ₂ HNOC HHH 2-Np cHx 2-420 3- (4-Tol) SO ₂ HNOC HHH 2-Np -CH (Ph) Me 2-421 4- ( 4-Tol) SO ₂ HNOC HHH 2-Np -CH (Ph) Me 2-422 2- [2- (2-Tol) P h] SO ₂ HNOC HHH 2-Np -CH (Ph) Me 2-423 3- [2- (2-Tol) Ph] SO ₂ HNOC HHH 2-Np 1-Et-Pn 2-424 3- [2- (2-Tol) Ph] SO ₂ HNOC HHH 2-Np cHx 2-425 3- [2- (2-Tol) Ph] SO ₂ HNOC HHH 2-Np -CH (Ph) Me 2-426 3- [2 -(3-Tol) Ph] SO ₂ HNOC HHH 2-Np 1-Et-Pn 2-427 3- [2- (3-Tol) Ph] SO ₂ HNOC HHH 2-Np cHx 2-428 3- [2 -(3-Tol) Ph] SO ₂ HNOC HHH 2-Np -CH (Ph) Me 2-429 3- [2- (4-Tol) Ph] SO ₂ HNOC HHH 2-Np 1-Et-Pn 2- 430 3- [2- (4-Tol) Ph] SO ₂ HNOC HHH 2-Np cHx 2-431 3- [2- (4-Tol) Ph] SO ₂ HNOC HHH 2-Np -CH (Ph) Me 2 -432 3- [3- (2-Tol) Ph] SO ₂ HNOC HHH 2-Np -CH (Ph) Me 2-433 3- [3- (3-Tol) Ph] SO ₂ HNOC HHH 2-Np- CH (Ph) Me 2-434 3- [3- (4-Tol) Ph] SO ₂ HNOC HHH 2-Np -CH (Ph) Me 2-435 3- [4- (2-Tol) Ph] SO ₂ HNOC HHH 2-Np -CH (Ph) Me 2-436 3- [4- (3-Tol) Ph] SO ₂ HNOC HHH 2-Np -CH (Ph) Me 2-437 3- [4- (4- Tol) Ph] SO ₂ HNOC HHH 2-Np -CH (Ph) Me 2-438 4- [2- (2-Tol) Ph] SO ₂ HNOC HHH 2-Np -CH (Ph) Me 2-439 4- [2- (3-Tol) Ph] SO ₂ HNOC HHH 2-Np -CH (Ph) Me 2-440 4- [2- (4-Tol) Ph] SO ₂ HNOC HHH 2-Np -CH (Ph) Me 2-441 4- [2- (2-Et-Ph) Ph] SO ₂ HNOC HHH 2-Np -CH (Ph) Me 2-442 4- [2- (2-MeO-Ph) Ph] SO ₂ HNOC HHH 2-N p -CH (Ph) Me 2-443 4- [2- (2-F-Ph) Ph] SO ₂ HNOC HHH 2-Np -CH (Ph) Me 2-444 2-MeSO ₂ HHH 2-Np 1- Et-Pn 2-445 2-MeSO ₂ HHH 2-Np 2-Et-Hx 2-446 2-MeSO ₂ HHH 2- (5-Me-Np) cHx 2-447 2-MeSO ₂ HHH 2-Np cHx 2 -448 2-MeSO ₂ HHH 2-Np Bz 2-449 2-MeSO ₂ HHH 2-Np -CH (Ph) Me 2-450 2-MeSO ₂ HHH 2-Np -CH (4-Br-Ph) Me 2 -451 2-MeSO ₂ HHH 2-Np -CH (1-Np) Me 2-452 3-MeSO ₂ HHH 2-Np 1-Et-Pn 2-453 3-MeSO ₂ HHH 2-Np cHx 2-454 3 -MeSO ₂ HHH 2-Np -CH (Ph) Me 2-455 4-MeSO ₂ HHH 2-Np 1-Et-Pn 2-456 4-MeSO ₂ HHH 2-Np 2-Et-Hx 2-457 4- MeSO ₂ HHH 2-Np cHx 2-458 4-MeSO ₂ HHH 2-Np Bz 2-459 4-MeSO ₂ HHH 2-Np -CH (Ph) Me 2-460 4-MeSO ₂ HHH 2-Np -CH ( 4-Br-Ph) Me 2-461 4-MeSO ₂ HHH 2-Np -CH (1-Np) Me 2-462 2-EtSO ₂ HHH 2-Np 1-Et-Pn 2-463 2-EtSO ₂ HHH 2-Np 2-Et-Hx 2-464 2-EtSO ₂ HHH 2- (5-Me-Np) cHx 2-465 2-EtSO ₂ HHH 2-Np cHx 2-466 2-EtSO ₂ HHH 2-Np Bz 2-467 2-EtSO ₂ HHH 2-Np -CH (Ph) Me 2-468 2-EtSO ₂ HHH 2-Np -CH (4-Br-Ph) Me 2-469 2-EtSO ₂ HHH 2-Np- CH (1-Np) Me 2-470 3-EtSO ₂ HHH 2-Np 1-Et-Pn 2-471 3-EtSO ₂ HHH 2-Np cHx 2-472 3-EtSO ₂ HHH 2-Np -CH (Ph) Me 2-473 4-EtSO ₂ HHH 2-Np 1-Et-Pn 2-474 4-EtSO ₂ HHH 2-Np 2-Et-Hx 2-475 4-EtSO ₂ HHH 2 -(5-Me-Np) cHx 2-476 4-EtSO ₂ HHH 2-Np cHx 2-477 4-EtSO ₂ HHH 2-Np -CH (Ph) Me 2-478 4-EtSO ₂ HHH 2-Np- CH (4-Br-Ph) Me 2-479 4-EtSO ₂ HHH 2-Np -CH (1-Np) Me 2-480 2-PrSO ₂ HHH 2-Np -CH (Ph) Me 2-481 4- PrSO ₂ HHH 2-Np -CH (Ph) Me 2-482 2-BuSO ₂ HHH 2-Np 1-Et-Pn 2-483 2-BuSO ₂ HHH 2- (5-Me-Np) cHx 2-484 2 -BuSO ₂ HHH 2-Np cHx 2-485 2-BuSO ₂ HHH 2-Np -CH (Ph) Me 2-486 2-BuSO ₂ HHH 2-Np -CH (4-Br-Ph) Me 2-487 2 -BuSO ₂ HHH 2-Np -CH (1-Np) Me 2-488 3-BuSO ₂ HHH 2-Np 1-Et-Pn 2-489 3-BuSO ₂ HHH 2-Np cHx 2-490 3-BuSO ₂ HHH 2-Np -CH (Ph) Me 2-491 4-BuSO ₂ HHH 2-Np 1-Et-Pn 2-492 4-BuSO ₂ HHH 2-Np cHx 2-493 4-BuSO ₂ HHH 2-Np- CH (Ph) Me 2-494 2-PhSO ₂ HHH 2-Np 1-Et-Pn 2-495 2-PhSO ₂ HHH 2-Np cHx 2-496 2-PhSO ₂ HHH 2-Np -CH (Ph) Me 2-497 3-PhSO ₂ HHH 2-Np cHx 2-498 4-PhSO ₂ HHH 2-Np cHx 2-499 2- (2-Tol) SO ₂ HNOCHN HHH 2-Np 1-Et-Pn 2-500 2 -(2-Tol) SO ₂ HNOCHN HHH 2-Np cHx 2-501 2- (2-Tol) SO ₂ HNOCHN HHH 2-Np -CH (Ph) Me 2-502 2- ( 3-Tol) SO ₂ HNOCHN HHH 2-Np 1-Et-Pn 2-503 2- (3-Tol) SO ₂ HNOCHN HHH 2-Np cHx 2-504 2- (3-Tol) SO ₂ HNOCHN HHH 2- Np -CH (Ph) Me 2-505 2- (4-Tol) SO ₂ HNOCHN HHH 2-Np 1-Et-Pn 2-506 2- (4-Tol) SO ₂ HNOCHN HHH 2-Np 2-Et- Hx 2-507 2- (4-Tol) SO ₂ HNOCHN HHH 2-Np cHx 2-508 2- (4-Tol) SO ₂ HNOCHN HHH 2-Np Bz 2-509 2- (4-Tol) SO ₂ HNOCHN HHH 2-Np -CH (Ph) Me 2-510 2- (4-Tol) SO ₂ HNOCHN HHH 2- (5-Me-Np) -CH (Ph) Me 2-511 2- (4-Tol) SO ₂ HNOCHN HHH 2-Np -CH (4-Br-Ph) Me 2-512 2- (4-Tol) SO ₂ HNOCHN HHH 2-Np -CH (1-Np) Me 2-513 3- (4-Tol ) SO ₂ HNOCHN HHH 2-Np -CH (Ph) Me 2-514 4- (4-Tol) SO ₂ HNOCHN HHH 2-Np -CH (Ph) Me 2-515 2- (4-Et-Ph) SO ₂ HNOCHN HHH 2-Np -CH (Ph) Me 2-516 2- (4-MeO-Ph) SO ₂ HNOCHN HHH 2-Np -CH (Ph) Me 2-517 2- (4-F-Ph) SO ₂ HNOCHN HHH 2-Np -CH (Ph) Me 2-518 2- (4-Cl-Ph) SO ₂ HNOCHN HHH 2-Np -CH (Ph) Me 2-519 2-MeSO HHH 2-Np -CH ( Ph) Me 2-520 2-EtSO HHH 2-Np -CH (Ph) Me 2-521 3-MeSO HHH 2-Np -CH (Ph) Me 2-522 4-MeSO HHH 2-Np -CH (Ph) Me .

[0089]

[Table 3]  R¹ R^Two R^Three R^Four R^5c R⁶  3-1 2- (2-MeSO_Two-Ph) H H H 2-Pyrr cHx 3-2 2- (2-MeSO_Two-Ph) H H H 3-Pyrr cHx 3-3 4- (2-MeSO_Two-Ph) H H H 2-Pyrr cHx 3-4 4- (2-MeSO_Two-Ph) HHH 3-Pyrr cHx 3-5 3-Tz HHH 2-Pyrr 1-Et-Pn 3-6 3-Tz HHH 2-Pyrr cHx 3-7 3-Tz HHH 2-Pyrr -CH (Ph) Me 3-8 3-Tz HHH 2- (4-Me-Pyrr) -CH (Ph) Me 3-9 3-Tz HHH 3-Pyrr 1-Et-Pn 3-10 3-Tz HHH 3-Pyrr cHx 3- 11 3-Tz HHH 3-Pyrr -CH (Ph) Me 3-12 3-Tz HHH 3- (5-Me-Pyrr) -CH (Ph) Me 3-13 4-Tz HHH 3-Pyrr 1-Et- Pn 3-14 4-Tz HHH 3-Pyrr cHx 3-15 4-Tz HHH 3-Pyrr -CH (Ph) Me 3-16 4-Tz HHH 3- (5-Me-Pyrr) -CH (Ph) Me 3-17 3- (4-Tol) SO_TwoHNOC H H H 2-Pyrr -CH (Ph) Me 3-18 3- (4-Tol) SO_TwoHNOC H H H 3-Pyrr -CH (Ph) Me 3-19 3- [2- (2-Tol) Ph] SO_TwoHNOC H H H 2-Pyrr -CH (Ph) Me 3-20 3- [2- (2-Tol) Ph] SO_TwoHNOC H H H 3-Pyrr -CH (Ph) Me 3-21 2-MeSO_Two H H H 2-Pyrr 1-Et-Pn 3-22 2-MeSO_Two H H H 2-Pyrr cHx 3-23 2-MeSO_Two H H H 2- (4-Me-Pyrr) cHx 3-24 2-MeSO_Two H H H 2-Pyrr -CH (Ph) Me 3-25 2-MeSO_Two H H H 3-Pyrr 1-Et-Pn 3-26 2-MeSO_Two H H H 3-Pyrr cHx 3-27 2-MeSO_Two H H H 3- (5-Me-Pyrr) cHx 3-28 2-MeSO_Two H H H 3-Pyrr -CH (Ph) Me 3-29 4-MeSO_Two H H H 2-Pyrr 1-Et-Pn 3-30 4-MeSO_Two H H H 2-Pyrr cHx 3-31 4-MeSO_Two H H H 2-Pyrr -CH (Ph) Me 3-32 4-MeSO_Two H H H 3-Pyrr 1-Et-Pn 3-33 4-MeSO_Two H H H 3-Pyrr cHx 3-34 4-MeSO_Two H H H 3-Pyrr -CH (Ph) Me 3-35 2-EtSO_Two H H H 2-Pyrr 1-Et-Pn 3-36 2-EtSO_Two H H H 2-Pyrr cHx 3-37 2-EtSO_Two H H H 2- (4-Me-Pyrr) cHx 3-38 2-EtSO_Two H H H 2-Pyrr -CH (Ph) Me 3-39 2-EtSO_Two H H H 3-Pyrr 1-Et-Pn 3-40 2-EtSO_Two H H H 3-Pyrr cHx 3-41 2-EtSO_Two H H H 3- (5-Me-Pyrr) cHx 3-42 2-EtSO_Two H H H 3-Pyrr -CH (Ph) Me 3-43 4-EtSO_Two H H H 2-Pyrr 1-Et-Pn 3-44 4-EtSO_Two H H H 2-Pyrr cHx 3-45 4-EtSO_Two H H H 2-Pyrr -CH (Ph) Me 3-46 4-EtSO_Two H H H 3-Pyrr 1-Et-Pn 3-47 4-EtSO_Two H H H 3-Pyrr cHx 3-48 4-EtSO_Two H H H 3-Pyrr -CH (Ph) Me 3-49 2-BuSO_Two H H H 2-Pyrr 1-Et-Pn 3-50 2-BuSO_Two H H H 2-Pyrr cHx 3-51 2-BuSO_Two H H H 2-Pyrr -CH (Ph) Me 3-52 2-BuSO_Two H H H 3-Pyrr 1-Et-Pn 3-53 2-BuSO_Two H H H 3-Pyrr cHx 3-54 2-BuSO_Two H H H 3-Pyrr -CH (Ph) Me 3-55 4-BuSO_Two H H H 2-Pyrr 1-Et-Pn 3-56 4-BuSO_Two H H H 2-Pyrr cHx 3-57 4-BuSO_Two H H H 2-Pyrr -CH (Ph) Me 3-58 4-BuSO_Two H H H 3-Pyrr 1-Et-Pn 3-59 4-BuSO_Two H H H 3-Pyrr cHx 3-60 4-BuSO_Two H H H 3-Pyrr -CH (Ph) Me 3-61 2-PhSO_Two H H H 2-Pyrr tBu 3-62 2-PhSO_Two H H H 3-Pyrr tBu 3-63 2- (4-Tol) SO_TwoHNOCHN H H H 2-Pyrr -CH (Ph) Me 3-64 2- (4-Tol) SO_TwoHNOCHN H H H 3-Pyrr -CH (Ph) Me 3-65 2-MeO H H H 2-Pyrr cHx 3-66 2-MeO H H H 3-Pyrr cHx 3-67 2- (2-MeSO_Two-Ph) H H H 2-Thi 2-Hep 3-68 2- (2-MeSO_Two-Ph) H H H 2-Thi cHx 3-69 2- (2-MeSO_Two-Ph) H H H 2-Thi -CH (Ph) Me 3-70 2- (2-MeSO_Two-Ph) H H H 2- (4-Me-Thi) -CH (Ph) Me 3-71 2- (2-MeSO_Two-Ph) H H H 3-Thi 2-Hep 3-72 2- (2-MeSO_Two-Ph) H H H 3-Thi cHx 3-73 2- (2-MeSO_Two-Ph) H H H 3-Thi -CH (Ph) Me 3-74 2- (2-MeSO_Two-Ph) H H H 3- (4-Me-Thi) -CH (Ph) Me 3-75 4- (2-MeSO_Two-Ph) H H H 2-Thi 2-Hep 3-76 4- (2-MeSO_Two-Ph) H H H 2-Thi cHx 3-77 4- (2-MeSO_Two-Ph) H H H 2-Thi -CH (Ph) Me 3-78 4- (2-MeSO_Two-Ph) H H H 2- (4-Me-Thi) -CH (Ph) Me 3-79 4- (2-MeSO_Two-Ph) H H H 3-Thi 2-Hep 3-80 4- (2-MeSO_Two-Ph) H H H 3-Thi cHx 3-81 4- (2-MeSO_Two-Ph) H H H 3-Thi -CH (Ph) Me 3-82 4- (2-MeSO_Two-Ph) HHH 3- (4-Me-Thi) -CH (Ph) Me 3-83 3-Tz HHH 2-Thi 1-Et-Pn 3-84 3-Tz HHH 2-Thi cHx 3-85 3- Tz HHH 2-Thi -CH (Ph) Me 3-86 3-Tz HHH 2- (4-Me-Thi) -CH (Ph) Me 3-87 3-Tz HHH 3-Thi 1-Et-Pn 3- 88 3-Tz HHH 3-Thi cHx 3-89 3-Tz HHH 3-Thi -CH (Ph) Me 3-90 3-Tz HHH 3- (5-Me-Thi) -CH (Ph) Me 3-91 4-Tz HHH 3-Thi 1-Et-Pn 3-92 4-Tz HHH 3-Thi cHx 3-93 4-Tz HHH 3-Thi -CH (Ph) Me 3-94 4-Tz HHH 3- (5 -Me-Thi) -CH (Ph) Me 3-95 3- (4-Tol) SO_TwoHNOC H H H 2-Thi -CH (Ph) Me 3-96 3- (4-Tol) SO_TwoHNOC H H H 3-Thi -CH (Ph) Me 3-97 3- [2- (2-Tol) Ph] SO_TwoHNOC H H H 2-Thi -CH (Ph) Me 3-98 3- [2- (2-Tol) Ph] SO_TwoHNOC H H H 3-Thi -CH (Ph) Me 3-99 2-MeSO_Two H H H 2-Thi 1-Et-Pn 3-100 2-MeSO_Two H H H 2-Thi cHx 3-101 2-MeSO_Two H H H 2- (4-Me-Thi) cHx 3-102 2-MeSO_Two H H H 2-Thi -CH (Ph) Me 3-103 2-MeSO_Two H H H 3-Thi 1-Et-Pn 3-104 2-MeSO_Two H H H 3-Thi cHx 3-105 2-MeSO_Two H H H 3- (5-Me-Thi) cHx 3-106 2-MeSO_Two H H H 3-Thi -CH (Ph) Me 3-107 4-MeSO_Two H H H 2-Thi 1-Et-Pn 3-108 4-MeSO_Two H H H 2-Thi cHx 3-109 4-MeSO_Two H H H 2-Thi -CH (Ph) Me 3-110 4-MeSO_Two H H H 3-Thi 1-Et-Pn 3-111 4-MeSO_Two H H H 3-Thi cHx 3-112 4-MeSO_Two H H H 3-Thi -CH (Ph) Me 3-113 2-EtSO_Two H H H 2-Thi 1-Et-Pn 3-114 2-EtSO_Two H H H 2-Thi cHx 3-115 2-EtSO_Two H H H 2- (4-Me-Thi) cHx 3-116 2-EtSO_Two H H H 2-Thi -CH (Ph) Me 3-117 2-EtSO_Two H H H 3-Thi 1-Et-Pn 3-118 2-EtSO_Two H H H 3-Thi cHx 3-119 2-EtSO_Two H H H 3- (5-Me-Thi) cHx 3-120 2-EtSO_Two H H H 3-Thi -CH (Ph) Me 3-121 4-EtSO_Two H H H 2-Thi 1-Et-Pn 3-122 4-EtSO_Two H H H 2-Thi cHx 3-123 4-EtSO_Two H H H 2-Thi -CH (Ph) Me 3-124 4-EtSO_Two H H H 3-Thi 1-Et-Pn 3-125 4-EtSO_Two H H H 3-Thi cHx 3-126 4-EtSO_Two H H H 3-Thi -CH (Ph) Me 3-127 2-BuSO_Two H H H 2-Thi 1-Et-Pn 3-128 2-BuSO_Two H H H 2-Thi cHx 3-129 2-BuSO_Two H H H 2-Thi -CH (Ph) Me 3-130 2-BuSO_Two H H H 3-Thi 1-Et-Pn 3-131 2-BuSO_Two H H H 3-Thi cHx 3-132 2-BuSO_Two H H H 3-Thi -CH (Ph) Me 3-133 4-BuSO_Two H H H 2-Thi 1-Et-Pn 3-134 4-BuSO_Two H H H 2-Thi cHx 3-135 4-BuSO_Two H H H 2-Thi -CH (Ph) Me 3-136 4-BuSO_Two H H H 3-Thi 1-Et-Pn 3-137 4-BuSO_Two H H H 3-Thi cHx 3-138 4-BuSO_Two H H H 3-Thi -CH (Ph) Me 3-139 2-PhSO_Two H H H 2-Thi tBu 3-140 2-PhSO_Two H H H 3-Thi tBu 3-141 2-PhSO_Two H H H 2-Thi cHx 3-142 2-PhSO_Two HHH 3-Thi cHx 3-143 2-MeSO HHH 2-Thi 1-Et-Pn 3-144 2-MeSO HHH 2-Thi cHx 3-145 2-MeSO HHH 2-Thi -CH (Ph) Me 3-146 2-MeSO HHH 3-Thi 1-Et-Pn 3-147 2-MeSO HHH 3-Thi cHx 3-148 2-MeSO HHH 3-Thi -CH (Ph) Me 3-149 4-MeSO HHH 2-Thi cHx 3-150 4-MeSO HHH 3-Thi cHx 3-151 2-EtSO HHH 2-Thi cHx 3-152 2-EtSO HHH 3-Thi cHx 3-153 2- (4-Tol) SO_TwoHNOCHN H H H 2-Thi -CH (Ph) Me 3-154 2- (4-Tol) SO_TwoHNOCHN H H H 3-Thi -CH (Ph) Me 3-155 4- (4-Tol) SO_TwoHNOCHN H H H 2-Thi -CH (Ph) Me 3-156 4- (4-Tol) SO_TwoHNOCHN HHH 3-Thi -CH (Ph) Me 3-157 3-Tz HHH 2-Thi -CH (4-Br-Ph) Me 3-158 4-Tz HHH 3-Thi -CH (4-Br-Ph) Me 3-159 2- (2-MeSO_Two-Ph) H H H 2- (1,1-dioxo-Thi) cHx 3-160 2- (2-MeSO_Two-Ph) H H H 3- (1,1-dioxo-Thi) cHx 3-161 4- (2-MeSO_Two-Ph) H H H 2- (1,1-dioxo-Thi) cHx 3-162 4- (2-MeSO_Two-Ph) HHH 3- (1,1-dioxo-Thi) cHx 3-163 3-Tz HHH 2- (1,1-dioxo-Thi) 1-Et-Pn 3-164 3-Tz HHH 2- (1 , 1-dioxo-Thi) cHx 3-165 3-Tz HHH 2- (1,1-dioxo-Thi) -CH (Ph) Me 3-166 3-Tz HHH -CH (Ph) Me R^5c= 2- (1,1-dioxo-4-Me-Thi) 3-167 3-Tz HHH 3- (1,1-dioxo-Thi) 1-Et-Pn 3-168 3-Tz HHH 3- (1 , 1-dioxo-Thi) cHx 3-169 3-Tz HHH 3- (1,1-dioxo-Thi) -CH (Ph) Me 3-170 3-Tz HHH -CH (Ph) Me R^5c= 3- (1,1-dioxo-5-Me-Thi) 3-171 4-Tz HHH 2- (1,1-dioxo-Thi) 1-Et-Pn 3-172 4-Tz HHH 2- (1 , 1-dioxo-Thi) cHx 3-173 4-Tz HHH 2- (1,1-dioxo-Thi) -CH (Ph) Me 3-174 4-Tz HHH 2- (1,1-dioxo-Thi) -CH (Ph) Me R^5c= 2- (1,1-dioxo-4-Me-Thi) 3-175 3- (4-Tol) SO_TwoHNOC H H H 2- (1,1-dioxo-Thi) -CH (Ph) Me 3-176 3- (4-Tol) SO_TwoHNOC H H H 3- (1,1-dioxo-Thi) -CH (Ph) Me 3-177 3- [2- (2-Tol) Ph] SO_TwoHNOC H H H 2- (1,1-dioxo-Thi) -CH (Ph) Me 3-178 3- [2- (2-Tol) Ph] SO_TwoHNOC H H H 3- (1,1-dioxo-Thi) -CH (Ph) Me 3-179 2-MeSO_Two H H H 2- (1,1-dioxo-Thi) 1-Et-Pn 3-180 2-MeSO_Two H H H 2- (1,1-dioxo-Thi) cHx 3-181 2-MeSO_Two H H H cHx R^5c= 2- (1,1-dioxo-4-Me-Thi) 3-182 2-MeSO_Two H H H 2- (1,1-dioxo-Thi) -CH (Ph) Me 3-183 2-MeSO_Two H H H 3- (1,1-dioxo-Thi) 1-Et-Pn 3-184 2-MeSO_Two H H H 3- (1,1-dioxo-Thi) cHx 3-185 2-MeSO_Two H H H cHx R^5c= 3- (1,1-dioxo-5-Me-Thi) 3-186 2-MeSO_Two H H H 3- (1,1-dioxo-Thi) -CH (Ph) Me 3-187 4-MeSO_Two H H H 2- (1,1-dioxo-Thi) 1-Et-Pn 3-188 4-MeSO_Two H H H 2- (1,1-dioxo-Thi) cHx 3-189 4-MeSO_Two H H H 2- (1,1-dioxo-Thi) -CH (Ph) Me 3-190 4-MeSO_Two H H H 3- (1,1-dioxo-Thi) 1-Et-Pn 3-191 4-MeSO_Two H H H 3- (1,1-dioxo-Thi) cHx 3-192 4-MeSO_Two H H H 3- (1,1-dioxo-Thi) -CH (Ph) Me 3-193 2-EtSO_Two H H H 2- (1,1-dioxo-Thi) 1-Et-Pn 3-194 2-EtSO_Two H H H 2- (1,1-dioxo-Thi) cHx 3-195 2-EtSO_Two H H H cHx R^5c= 2- (1,1-dioxo-4-Me-Thi) 3-196 2-EtSO_Two H H H 2- (1,1-dioxo-Thi) -CH (Ph) Me 3-197 2-EtSO_Two H H H 3- (1,1-dioxo-Thi) 1-Et-Pn 3-198 2-EtSO_Two H H H 3- (1,1-dioxo-Thi) cHx 3-199 2-EtSO_Two H H H cHx R^5c= 3- (1,1-dioxo-5-Me-Thi) 3-200 2-EtSO_Two H H H 3- (1,1-dioxo-Thi) -CH (Ph) Me 3-201 4-EtSO_Two H H H 2- (1,1-dioxo-Thi) 1-Et-
Pn 3-203 4-EtSO_Two H H H 2- (1,1-dioxo-Thi) -CH (Ph) Me 3-204 4-EtSO_Two H H H 3- (1,1-dioxo-Thi) 1-Et-Pn 3-205 4-EtSO_Two H H H 3- (1,1-dioxo-Thi) cHx 3-206 4-EtSO_Two H H H 3- (1,1-dioxo-Thi) -CH (Ph) Me 3-207 2-BuSO_Two H H H 2- (1,1-dioxo-Thi) 1-Et-Pn 3-208 2-BuSO_Two H H H 2- (1,1-dioxo-Thi) cHx 3-209 2-BuSO_Two H H H 2- (1,1-dioxo-Thi) -CH (Ph) Me 3-210 2-BuSO_Two H H H 3- (1,1-dioxo-Thi) 1-Et-Pn 3-211 2-BuSO_Two H H H 3- (1,1-dioxo-Thi) cHx 3-212 2-BuSO_Two H H H 3- (1,1-dioxo-Thi) -CH (Ph) Me 3-213 4-BuSO_Two H H H 2- (1,1-dioxo-Thi) 1-Et-Pn 3-214 4-BuSO_Two H H H 2- (1,1-dioxo-Thi) cHx 3-215 4-BuSO_Two H H H 2- (1,1-dioxo-Thi) -CH (Ph) Me 3-216 4-BuSO_Two H H H 3- (1,1-dioxo-Thi) 1-Et-Pn 3-217 4-BuSO_Two H H H 3- (1,1-dioxo-Thi) cHx 3-218 4-BuSO_Two H H H 3- (1,1-dioxo-Thi) -CH (Ph) Me 3-219 2-PhSO_Two H H H 2- (1,1-dioxo-Thi) tBu 3-220 2-PhSO_Two H H H 3- (1,1-dioxo-Thi) tBu 3-221 2- (4-Tol) SO_TwoHNOCHN H H H 2- (1,1-dioxo-Thi) -CH (Ph) Me 3-222 2- (4-Tol) SO_TwoHNOCHN HHH 3- (1,1-dioxo-Thi) -CH (Ph) Me 3-223 3-Tz HHH 2- (1,1-dioxo-Thi) -CH (4-Br-Ph) Me 3-224 4-Tz HHH 3- (1,1-dioxo-Thi) -CH (4-Br-Ph) Me 3-225 2- (2-MeSO_Two-Ph) H H H 2-Thiz 2-Hep 3-226 2- (2-MeSO_Two-Ph) H H H 2-Thiz cHx 3-227 2- (2-MeSO_Two-Ph) H H H 2-Thiz -CH (Ph) Me 3-228 2- (2-MeSO_Two-Ph) H H H 3-Thiz 2-Hep 3-229 2- (2-MeSO_Two-Ph) H H H 3-Thiz cHx 3-230 2- (2-MeSO_Two-Ph) H H H 3-Thiz -CH (Ph) Me 3-231 4- (2-MeSO_Two-Ph) H H H 2-Thiz 2-Hep 3-232 4- (2-MeSO_Two-Ph) H H H 2-Thiz cHx 3-233 4- (2-MeSO_Two-Ph) H H H 2-Thiz -CH (Ph) Me 3-234 4- (2-MeSO_Two-Ph) H H H 3-Thiz 2-Hep 3-235 4- (2-MeSO_Two-Ph) H H H 3-Thiz cHx 3-236 4- (2-MeSO_Two-Ph) HHH 3-Thiz -CH (Ph) Me 3-237 3-Tz HHH 2-Thiz 1-Et-Pn 3-238 3-Tz HHH 2-Thiz cHx 3-239 3-Tz HHH 2-Thiz- CH (Ph) Me 3-240 3-Tz HHH 3-Thiz 1-Et-Pn 3-241 3-Tz HHH 3-Thiz cHx 3-242 3-Tz HHH 3-Thiz -CH (Ph) Me 3-243 4-Tz HHH 3-Thiz 1-Et-Pn 3-244 4-Tz HHH 3-Thiz cHx 3-245 4-Tz HHH 3-Thiz -CH (Ph) Me 3-246 3- (4-Tol) SO_TwoHNOC H H H 2-Thiz -CH (Ph) Me 3-247 3- (4-Tol) SO_TwoHNOC H H H 3-Thiz -CH (Ph) Me 3-248 3- [2- (2-Tol) Ph] SO_TwoHNOC H H H 2-Thiz -CH (Ph) Me 3-249 3- [2- (2-Tol) Ph] SO_TwoHNOC H H H 3-Thiz -CH (Ph) Me 3-250 2-MeSO_Two H H H 2-Thiz 1-Et-Pn 3-251 2-MeSO_Two H H H 2-Thiz cHx 3-252 2-MeSO_Two H H H 2-Thiz -CH (Ph) Me 3-253 2-MeSO_Two H H H 3-Thiz 1-Et-Pn 3-254 2-MeSO_Two H H H 3-Thiz cHx 3-255 2-MeSO_Two H H H 3-Thiz -CH (Ph) Me 3-256 4-MeSO_Two H H H 2-Thiz 1-Et-Pn 3-257 4-MeSO_Two H H H 2-Thiz cHx 3-258 4-MeSO_Two H H H 2-Thiz -CH (Ph) Me 3-259 4-MeSO_Two H H H 3-Thiz 1-Et-Pn 3-260 4-MeSO_Two H H H 3-Thiz cHx 3-261 4-MeSO_Two H H H 3-Thiz -CH (Ph) Me 3-262 2-EtSO_Two H H H 2-Thiz 1-Et-Pn 3-263 2-EtSO_Two H H H 2-Thiz cHx 3-264 2-EtSO_Two H H H 2-Thiz -CH (Ph) Me 3-265 2-EtSO_Two H H H 3-Thiz 1-Et-Pn 3-266 2-EtSO_Two H H H 3-Thiz cHx 3-267 2-EtSO_Two H H H 3-Thiz -CH (Ph) Me 3-268 4-EtSO_Two H H H 2-Thiz 1-Et-Pn 3-269 4-EtSO_Two H H H 2-Thiz cHx 3-270 4-EtSO_Two H H H 2-Thiz -CH (Ph) Me 3-271 4-EtSO_Two H H H 3-Thiz 1-Et-Pn 3-272 4-EtSO_Two H H H 3-Thiz cHx 3-273 4-EtSO_Two H H H 3-Thiz -CH (Ph) Me 3-274 2-BuSO_Two H H H 2-Thiz 1-Et-Pn 3-275 2-BuSO_Two H H H 2-Thiz cHx 3-276 2-BuSO_Two H H H 2-Thiz -CH (Ph) Me 3-277 2-BuSO_Two H H H 3-Thiz 1-Et-Pn 3-278 2-BuSO_Two H H H 3-Thiz cHx 3-279 2-BuSO_Two H H H 3-Thiz -CH (Ph) Me 3-280 4-BuSO_Two H H H 2-Thiz 1-Et-Pn 3-281 4-BuSO_Two H H H 2-Thiz cHx 3-282 4-BuSO_Two H H H 2-Thiz -CH (Ph) Me 3-283 4-BuSO_Two H H H 3-Thiz 1-Et-Pn 3-284 4-BuSO_Two H H H 3-Thiz cHx 3-285 4-BuSO_Two H H H 3-Thiz -CH (Ph) Me 3-286 2-PhSO_Two H H H 2-Thiz tBu 3-287 2-PhSO_Two H H H 3-Thiz tBu 3-288 2- (4-Tol) SO_TwoHNOCHN H H H 2-Thiz -CH (Ph) Me 3-289 2- (4-Tol) SO_TwoHNOCHN H H H 3-Thiz -CH (Ph) Me 3-290 4- (4-Tol) SO_TwoHNOCHN H H H 2-Thiz -CH (Ph) Me 3-291 4- (4-Tol) SO_TwoHNOCHN HHH 3-Thiz -CH (Ph) Me 3-292 3-Tz HHH 2-Thiz -CH (4-Br-Ph) Me 3-293 4-Tz HHH 3-Thiz -CH (4-Br-Ph) Me 3-294 2- (2-MeSO_Two-Ph) H H H 2-Ind cHx 3-295 2- (2-MeSO_Two-Ph) H H H 3-Ind cHx 3-296 4- (2-MeSO_Two-Ph) H H H 2-Ind cHx 3-297 4- (2-MeSO_Two-Ph) HHH 3-Ind cHx 3-298 3-Tz HHH 2-Ind -CH (Ph) Me 3-299 3-Tz HHH 3-Ind -CH (Ph) Me 3-300 4-Tz HHH 2-Ind 1-Et-Pn 3-301 4-Tz HHH 3-Ind 1-Et-Pn 3-302 3- (4-Tol) SO_TwoHNOC H H H 2-Ind -CH (Ph) Me 3-303 3- (4-Tol) SO_TwoHNOC H H H 3-Ind -CH (Ph) Me 3-304 3- [2- (2-Tol) Ph] SO_TwoHNOC H H H 2-Ind -CH (Ph) Me 3-305 3- [2- (2-Tol) Ph] SO_TwoHNOC H H H 3-Ind -CH (Ph) Me 3-306 2-MeSO_Two H H H 2-Ind 1-Et-Pn 3-307 2-MeSO_Two H H H 2-Ind cHx 3-308 2-MeSO_Two H H H 2- (4-Me-Ind) cHx 3-309 2-MeSO_Two H H H 2-Ind -CH (Ph) Me 3-310 2-MeSO_Two H H H 3-Ind 1-Et-Pn 3-311 2-MeSO_Two H H H 3-Ind cHx 3-312 2-MeSO_Two H H H 3- (5-Me-Ind) cHx 3-313 2-MeSO_Two H H H 3-Ind -CH (Ph) Me 3-314 4-MeSO_Two H H H 2-Ind 1-Et-Pn 3-315 4-MeSO_Two H H H 2-Ind cHx 3-316 4-MeSO_Two H H H 2-Ind -CH (Ph) Me 3-317 4-MeSO_Two H H H 3-Ind 1-Et-Pn 3-318 4-MeSO_Two H H H 3-Ind cHx 3-319 4-MeSO_Two H H H 3-Ind -CH (Ph) Me 3-320 2-EtSO_Two H H H 2-Ind 1-Et-Pn 3-321 2-EtSO_Two H H H 2-Ind cHx 3-322 2-EtSO_Two H H H 2- (4-Me-Ind) cHx 3-323 2-EtSO_Two H H H 2-Ind -CH (Ph) Me 3-324 2-EtSO_Two H H H 3-Ind 1-Et-Pn 3-325 2-EtSO_Two H H H 3-Ind cHx 3-326 2-EtSO_Two H H H 3- (5-Me-Ind) cHx 3-327 2-EtSO_Two H H H 3-Ind -CH (Ph) Me 3-328 4-EtSO_Two H H H 2-Ind 1-Et-Pn 3-329 4-EtSO_Two H H H 2-Ind cHx 3-330 4-EtSO_Two H H H 2-Ind -CH (Ph) Me 3-331 4-EtSO_Two H H H 3-Ind 1-Et-Pn 3-332 4-EtSO_Two H H H 3-Ind cHx 3-333 4-EtSO_Two H H H 3-Ind -CH (Ph) Me 3-334 2-PhSO_Two H H H 2-Ind tBu 3-335 2-PhSO_Two H H H 3-Ind tBu 3-336 2- (4-Tol) SO_TwoHNOCHN H H H 2-Ind -CH (Ph) Me 3-337 2- (4-Tol) SO_TwoHNOCHN HHH 3-Ind -CH (Ph) Me 3-338 3-Tz HHH 2-Ind -CH (4-Br-Ph) Me 3-339 4-Tz HHH 3-Ind -CH (4-Br-Ph) Me 3-340 2- (2-MeSO_Two-Ph) H H H 2-BThi cHx 3-341 2- (2-MeSO_Two-Ph) H H H 3-BThi cHx 3-342 4- (2-MeSO_Two-Ph) H H H 2-BThi cHx 3-343 4- (2-MeSO_Two-Ph) HHH 3-BThi cHx 3-344 3-Tz HHH 2-BThi -CH (Ph) Me 3-345 3-Tz HHH 3-BThi -CH (Ph) Me 3-346 4-Tz HHH 2-BThi 1-Et-Pn 3-347 4-Tz HHH 3-BThi 1-Et-Pn 3-348 3- (4-Tol) SO_TwoHNOC H H H 2-BThi -CH (Ph) Me 3-449 3- (4-Tol) SO_TwoHNOC H H H 3-BThi -CH (Ph) Me 3-350 3- [2- (2-Tol) Ph] SO_TwoHNOC H H H 2-BThi -CH (Ph) Me 3-351 3- [2- (2-Tol) Ph] SO_TwoHNOC H H H 3-BThi -CH (Ph) Me 3-352 2-MeSO_Two H H H 2-BThi 1-Et-Pn 3-353 2-MeSO_Two H H H 2-BThi cHx 3-354 2-MeSO_Two H H H 2- (4-Me-BThi) cHx 3-355 2-MeSO_Two H H H 2-BThi -CH (Ph) Me 3-356 2-MeSO_Two H H H 3-BThi 1-Et-Pn 3-357 2-MeSO_Two H H H 3-BThi cHx 3-358 2-MeSO_Two H H H 3- (5-Me-BThi) cHx 3-359 2-MeSO_Two H H H 3-BThi -CH (Ph) Me 3-360 4-MeSO_Two H H H 2-BThi 1-Et-Pn 3-361 4-MeSO_Two H H H 2-BThi cHx 3-362 4-MeSO_Two H H H 2-BThi -CH (Ph) Me 3-363 4-MeSO_Two H H H 3-BThi 1-Et-Pn 3-364 4-MeSO_Two H H H 3-BThi cHx 3-365 4-MeSO_Two H H H 3-BThi -CH (Ph) Me 3-366 2-EtSO_Two H H H 2-BThi 1-Et-Pn 3-367 2-EtSO_Two H H H 2-BThi cHx 3-368 2-EtSO_Two H H H 2- (4-Me-BThi) cHx 3-369 2-EtSO_Two H H H 2-BThi -CH (Ph) Me 3-370 2-EtSO_Two H H H 3-BThi 1-Et-Pn 3-371 2-EtSO_Two H H H 3-BThi cHx 3-372 2-EtSO_Two H H H 3- (5-Me-BThi) cHx 3-373 2-EtSO_Two H H H 3-BThi -CH (Ph) Me 3-374 4-EtSO_Two H H H 2-BThi 1-Et-Pn 3-375 4-EtSO_Two H H H 2-BThi cHx 3-376 4-EtSO_Two H H H 2-BThi -CH (Ph) Me 3-377 4-EtSO_Two H H H 3-BThi 1-Et-Pn 3-378 4-EtSO_Two H H H 3-BThi cHx 3-379 4-EtSO_Two H H H 3-BThi -CH (Ph) Me 3-380 2-PhSO_Two H H H 2-BThi tBu 3-381 2-PhSO_Two H H H 3-BThi tBu 3-382 2- (4-Tol) SO_TwoHNOCHN H H H 2-BThi -CH (Ph) Me 3-383 2- (4-Tol) SO_TwoHNOCHN HHH 3-BThi -CH (Ph) Me 3-384 3-Tz HHH 2-BThi -CH (4-Br-Ph) Me 3-385 4-Tz HHH 3-BThi -CH (4-Br-Ph) Me 3-386 2- (2-MeSO_Two-Ph) H H H 2- (1,1-dioxo-BThi) 2-Hep 3-387 2- (2-MeSO_Two-Ph) H H H 2- (1,1-dioxo-BThi) cHx 3-388 2- (2-MeSO_Two-Ph) H H H 2- (1,1-dioxo-BThi) -CH (Ph) Me 3-389 2- (2-MeSO_Two-Ph) H H H -CH (Ph) Me R^5c= 2- (1,1-dioxo-4-Me-BThi) 3-390 2- (2-MeSO_Two-Ph) H H H 3- (1,1-dioxo-BThi) 2-Hep 3-391 2- (2-MeSO_Two-Ph) H H H 3- (1,1-dioxo-BThi) cHx 3-392 2- (2-MeSO_Two-Ph) H H H 3- (1,1-dioxo-BThi) -CH (Ph) Me 3-393 2- (2-MeSO_Two-Ph) H H H -CH (Ph) Me R^5c= 3- (1,1-dioxo-4-Me-BThi) 3-394 4- (2-MeSO_Two-Ph) H H H 2- (1,1-dioxo-BThi) 2-Hep 3-395 4- (2-MeSO_Two-Ph) H H H 2- (1,1-dioxo-BThi) cHx 3-396 4- (2-MeSO_Two-Ph) H H H 2- (1,1-dioxo-BThi) -CH (Ph) Me 3-397 4- (2-MeSO_Two-Ph) H H H -CH (Ph) Me R^5c= 2- (1,1-dioxo-4-Me-BThi) 3-398 4- (2-MeSO_Two-Ph) H H H 3- (1,1-dioxo-BThi) 2-Hep 3-399 4- (2-MeSO_Two-Ph) H H H 3- (1,1-dioxo-BThi) cHx 3-400 4- (2-MeSO_Two-Ph) H H H 3- (1,1-dioxo-BThi) -CH (Ph) Me 3-401 4- (2-MeSO_Two-Ph) H H H -CH (Ph) Me R^5c= 3- (1,1-dioxo-4-Me-BThi) 3-402 3-Tz HHH 2- (1,1-dioxo-BThi) 1-Et-Pn 3-403 3-Tz HHH 2- (1 , 1-dioxo-BThi) cHx 3-404 3-Tz HHH 2- (1,1-dioxo-BThi) -CH (PH) Me 3-405 3-Tz HHH -CH (PH) Me R^5c= 2- (1,1-dioxo-4-Me-BThi) 3-406 3-Tz HHH 3- (1,1-dioxo-BThi) 1-Et-Pn 3-407 3-Tz HHH 3- (1 , 1-dioxo-BThi) cHx 3-408 3-Tz HHH 3- (1,1-dioxo-BThi) -CH (PH) Me 3-409 3-Tz HHH -CH (PH) Me R^5c= 3- (1,1-dioxo-5-Me-BThi) 3-410 4-Tz HHH 3- (1,1-dioxo-BThi) 1-Et-Pn 3-411 4-Tz HHH 3- (1 , 1-dioxo-BThi) cHx 3-412 4-Tz HHH 3- (1,1-dioxo-BThi) -CH (PH) Me 3-413 4-Tz HHH -CH (PH) Me R^5c= 3- (1,1-dioxo-5-Me-BThi) 3-414 3- (4-Tol) SO_TwoHNOC H H H 2- (1,1-dioxo-BThi) -CH (Ph) Me 3-415 3- (4-Tol) SO_TwoHNOC H H H 3- (1,1-dioxo-BThi) -CH (Ph) Me 3-416 3- [2- (2-Tol) Ph] SO_TwoHNOC H H H 2- (1,1-dioxo-BThi) -CH (Ph) Me 3-417 3- [2- (2-Tol) Ph] SO_TwoHNOC H H H 3- (1,1-dioxo-BThi) -CH (Ph) Me 3-418 2-MeSO_Two H H H 2- (1,1-dioxo-BThi) 1-Et-Pn 3-419 2-MeSO_Two H H H 2- (1,1-dioxo-BThi) cHx 3-420 2-MeSO_Two H H H cHx R^5c= 2- (1,1-dioxo-4-Me-BThi) 3-421 2-MeSO_Two H H H 2- (1,1-dioxo-BThi) -CH (Ph) Me 3-422 2-MeSO_Two H H H 3- (1,1-dioxo-BThi) 1-Et-Pn 3-423 2-MeSO_Two H H H 3- (1,1-dioxo-BThi) cHx 3-424 2-MeSO_Two H H H cHx R^5c= 3- (1,1-dioxo-5-Me-BThi) 3-425 2-MeSO_Two H H H 3- (1,1-dioxo-BThi) -CH (Ph) Me 3-426 4-MeSO_Two H H H 2- (1,1-dioxo-BThi) 1-Et-Pn 3-427 4-MeSO_Two H H H 2- (1,1-dioxo-BThi) cHx 3-428 4-MeSO_Two H H H 2- (1,1-dioxo-BThi) -CH (Ph) Me 3-429 4-MeSO_Two H H H 3- (1,1-dioxo-BThi) 1-Et-Pn 3-430 4-MeSO_Two H H H 3- (1,1-dioxo-BThi) cHx 3-431 4-MeSO_Two H H H 3- (1,1-dioxo-BThi) -CH (Ph) Me 3-432 2-EtSO_Two H H H 2- (1,1-dioxo-BThi) 1-Et-Pn 3-433 2-EtSO_Two H H H 2- (1,1-dioxo-BThi) cHx 3-434 2-EtSO_Two H H H cHx R^5c= 2- (1,1-dioxo-4-Me-BThi) 3-435 2-EtSO_Two H H H 2- (1,1-dioxo-BThi) -CH (Ph) Me 3-436 2-EtSO_Two H H H 3- (1,1-dioxo-BThi) 1-Et-Pn 3-437 2-EtSO_Two H H H 3- (1,1-dioxo-BThi) cHx 3-438 2-EtSO_Two H H H cHx R^5c= 3- (1,1-dioxo-5-Me-BThi) 3-439 2-EtSO_Two H H H 3- (1,1-dioxo-BThi) -CH (Ph) Me 3-440 4-EtSO_Two H H H 2- (1,1-dioxo-BThi) 1-Et-Pn 3-441 4-EtSO_Two H H H 2- (1,1-dioxo-BThi) cHx 3-442 4-EtSO_Two H H H 2- (1,1-dioxo-BThi) -CH (Ph) Me 3-443 4-EtSO_Two H H H 3- (1,1-dioxo-BThi) 1-Et-Pn 3-445 4-EtSO_Two H H H 3- (1,1-dioxo-BThi) -CH (Ph) Me 3-446 2-BuSO_Two H H H 2- (1,1-dioxo-BThi) 1-Et-Pn 3-447 2-BuSO_Two H H H 2- (1,1-dioxo-BThi) cHx 3-448 2-BuSO_Two H H H 2- (1,1-dioxo-BThi) -CH (Ph) Me 3-449 2-BuSO_Two H H H 3- (1,1-dioxo-BThi) 1-Et-Pn 3-450 2-BuSO_Two H H H 3- (1,1-dioxo-BThi) cHx 3-451 2-BuSO_Two H H H 3- (1,1-dioxo-BThi) -CH (Ph) Me 3-452 4-BuSO_Two H H H 2- (1,1-dioxo-BThi) 1-Et-Pn 3-453 4-BuSO_Two H H H 2- (1,1-dioxo-BThi) cHx 3-454 4-BuSO_Two H H H 2- (1,1-dioxo-BThi) -CH (Ph) Me 3-455 4-BuSO_Two H H H 3- (1,1-dioxo-BThi) 1-Et-Pn 3-456 4-BuSO_Two H H H 3- (1,1-dioxo-BThi) cHx 3-457 4-BuSO_Two H H H 3- (1,1-dioxo-BThi) -CH (Ph) Me 3-458 2-PhSO_Two H H H 2- (1,1-dioxo-BThi) tBu 3-459 2-PhSO_Two H H H 3- (1,1-dioxo-BThi) tBu 3-460 2- (4-Tol) SO_TwoHNOCHN H H H 2- (1,1-dioxo-BThi) -CH (Ph) Me 3-461 2- (4-Tol) SO_TwoHNOCHN H H H 3- (1,1-dioxo-BThi) -CH (Ph) Me 3-462 4- (4-Tol) SO_TwoHNOCHN H H H 2- (1,1-dioxo-BThi) -CH (Ph) Me 3-463 4- (4-Tol) SO_TwoHNOCHN H H H 3- (1,1-dioxo-BThi) -CH (Ph) Me 3-464 3-Tz H H H -CH (4-Br-Ph) Me R^5c= 2- (1,1-dioxo-BThi) 3-465 4-Tz H H H -CH (4-Br-Ph) Me R^5c= 2- (1,1-dioxo-BThi) 3-466 2- (2-MeSO_Two-Ph) H H H 2-BThiz cHx 3-467 2- (2-MeSO_Two-Ph) H H H 3-BThiz cHx 3-468 4- (2-MeSO_Two-Ph) H H H 2-BThiz cHx 3-469 4- (2-MeSO_Two-Ph) HHH 3-BThiz cHx 3-470 3-Tz HHH 2-BThiz -CH (Ph) Me 3-472 4-Tz HHH 2-BThiz 1-Et-Pn 3-473 4-Tz HHH 3-BThiz 1 -Et-Pn 3-474 3- (4-Tol) SO_TwoHNOC H H H 2-BThiz -CH (Ph) Me 3-475 3- (4-Tol) SO_TwoHNOC H H H 3-BThiz -CH (Ph) Me 3-476 3- [2- (2-Tol) Ph] SO_TwoHNOC H H H 2-BThiz -CH (Ph) Me 3-477 3- [2- (2-Tol) Ph] SO_TwoHNOC H H H 3-BThiz -CH (Ph) Me 3-478 2-MeSO_Two H H H 2-BThiz 1-Et-Pn 3-479 2-MeSO_Two H H H 2-BThiz cHx 3-480 2-MeSO_Two H H H 2- (4-Me-BThiz) cHx 3-481 2-MeSO_Two H H H 2-BThiz -CH (Ph) Me 3-482 2-MeSO_Two H H H 3-BThiz 1-Et-Pn 3-483 2-MeSO_Two H H H 3-BThiz cHx 3-484 2-MeSO_Two H H H 3- (5-Me-BThiz) cHx 3-485 2-MeSO_Two H H H 3-BThiz -CH (Ph) Me 3-486 4-MeSO_Two H H H 2-BThiz 1-Et-Pn 3-487 4-MeSO_Two H H H 2-BThiz cHx 3-488 4-MeSO_Two H H H 2-BThiz -CH (Ph) Me 3-489 4-MeSO_Two H H H 3-BThiz 1-Et-Pn 3-490 4-MeSO_Two H H H 3-BThiz cHx 3-491 4-MeSO_Two H H H 3-BThiz -CH (Ph) Me 3-492 2-EtSO_Two H H H 2-BThiz 1-Et-Pn 3-493 2-EtSO_Two H H H 2-BThiz cHx 3-494 2-EtSO_Two H H H 2- (4-Me-BThiz) cHx 3-495 2-EtSO_Two H H H 2-BThiz -CH (Ph) Me 3-496 2-EtSO_Two H H H 3-BThiz 1-Et-Pn 3-497 2-EtSO_Two H H H 3-BThiz cHx 3-498 2-EtSO_Two H H H 3- (5-Me-BThiz) cHx 3-499 2-EtSO_Two H H H 3-BThiz -CH (Ph) Me 3-500 4-EtSO_Two H H H 2-BThiz 1-Et-Pn 3-501 4-EtSO_Two H H H 2-BThiz cHx 3-502 4-EtSO_Two H H H 2-BThiz -CH (Ph) Me 3-503 4-EtSO_Two H H H 3-BThiz 1-Et-Pn 3-504 4-EtSO_Two H H H 3-BThiz cHx 3-505 4-EtSO_Two H H H 3-BThiz -CH (Ph) Me 3-506 2-PhSO_Two H H H 2-BThiz tBu 3-507 2-PhSO_Two H H H 3-BThiz tBu 3-508 2- (4-Tol) SO_TwoHNOCHN H H H 2-BThiz -CH (Ph) Me 3-509 2- (4-Tol) SO_TwoHNOCHN HHH 3-BThiz -CH (Ph) Me 3-510 3-Tz HHH 2-BThiz -CH (4-Br-Ph) Me 3-511 4-Tz HHH 3-BThiz -CH (4-Br-Ph) Me 3-512 2- (2-MeSO_Two-Ph) H H H 2-Oxa cHx 3-513 2- (2-MeSO_Two-Ph) H H H 3-Oxa cHx 3-514 4- (2-MeSO_Two-Ph) H H H 2-Oxa cHx 3-515 4- (2-MeSO_Two-Ph) HHH 3-Oxa cHx 3-516 3-Tz HHH 2-Oxa -CH (Ph) Me 3-517 3-Tz HHH 3-Oxa -CH (Ph) Me 3-518 4-Tz HHH 2-Oxa 1-Et-Pn 3-519 4-Tz HHH 3-Oxa 1-Et-Pn 3-520 3- (4-Tol) SO_TwoHNOC H H H 2-Oxa -CH (Ph) Me 3-521 3- (4-Tol) SO_TwoHNOC H H H 3-Oxa -CH (Ph) Me 3-522 3- [2- (2-Tol) Ph] SO_TwoHNOC H H H 2-Oxa -CH (Ph) Me 3-523 3- [2- (2-Tol) Ph] SO_TwoHNOC H H H 3-Oxa -CH (Ph) Me 3-524 2-MeSO_Two H H H 2-Oxa 1-Et-Pn 3-525 2-MeSO_Two H H H 2-Oxa cHx 3-526 2-MeSO_Two H H H 2- (4-Me-Oxa) cHx 3-527 2-MeSO_Two H H H 2-Oxa -CH (Ph) Me 3-528 2-MeSO_Two H H H 3-Oxa 1-Et-Pn 3-529 2-MeSO_Two H H H 3-Oxa cHx 3-530 2-MeSO_Two H H H 3- (5-Me-Oxa) cHx 3-531 2-MeSO_Two H H H 3-Oxa -CH (Ph) Me 3-532 4-MeSO_Two H H H 2-Oxa 1-Et-Pn 3-533 4-MeSO_Two H H H 2-Oxa cHx 3-534 4-MeSO_Two H H H 2-Oxa -CH (Ph) Me 3-535 4-MeSO_Two H H H 3-Oxa 1-Et-Pn 3-536 4-MeSO_Two H H H 3-Oxa cHx 3-537 4-MeSO_Two H H H 3-Oxa -CH (Ph) Me 3-538 2-EtSO_Two H H H 2-Oxa 1-Et-Pn 3-539 2-EtSO_Two H H H 2-Oxa cHx 3-540 2-EtSO_Two H H H 2- (4-Me-Oxa) cHx 3-541 2-EtSO_Two H H H 2-Oxa -CH (Ph) Me 3-542 2-EtSO_Two H H H 3-Oxa 1-Et-Pn 3-543 2-EtSO_Two H H H 3-Oxa cHx 3-544 2-EtSO_Two H H H 3- (5-Me-Oxa) cHx 3-545 2-EtSO_Two H H H 3-Oxa -CH (Ph) Me 3-546 4-EtSO_Two H H H 2-Oxa 1-Et-Pn 3-547 4-EtSO_Two H H H 2-Oxa cHx 3-548 4-EtSO_Two H H H 2-Oxa -CH (Ph) Me 3-549 4-EtSO_Two H H H 3-Oxa 1-Et-Pn 3-550 4-EtSO_Two H H H 3-Oxa cHx 3-551 4-EtSO_Two H H H 3-Oxa -CH (Ph) Me 3-552 2-PhSO_Two H H H 2-Oxa tBu 3-553 2-PhSO_Two H H H 3-Oxa tBu 3-555 2- (4-Tol) SO_TwoHNOCHN HHH 3-Oxa -CH (Ph) Me 3-556 3-Tz HHH 2-Oxa -CH (4-Br-Ph) Me 3-557 4-Tz HHH 3-Oxa -CH (4-Br-Ph) Me 3-558 2- (2-MeSO_Two-Ph) H H H 2-BOxa cHx 3-559 2- (2-MeSO_Two-Ph) H H H 3-BOxa cHx 3-560 4- (2-MeSO_Two-Ph) H H H 2-BOxa cHx 3-561 4- (2-MeSO_Two-Ph) HHH 3-BOxa cHx 3-562 3-Tz HHH 2-BOxa -CH (Ph) Me 3-563 3-Tz HHH 3-BOxa -CH (Ph) Me 3-564 4-Tz HHH 2-BOxa 1-Et-Pn 3-565 4-Tz HHH 3-BOxa 1-Et-Pn 3-566 3- (4-Tol) SO_TwoHNOC H H H 2-BOxa -CH (Ph) Me 3-567 3- (4-Tol) SO_TwoHNOC H H H 3-BOxa -CH (Ph) Me 3-568 3- [2- (2-Tol) Ph] SO_TwoHNOC H H H 2-BOxa -CH (Ph) Me 3-569 3- [2- (2-Tol) Ph] SO_TwoHNOC H H H 3-BOxa -CH (Ph) Me 3-570 2-MeSO_Two H H H 2-BOxa 1-Et-Pn 3-571 2-MeSO_Two H H H 2-BOxa cHx 3-572 2-MeSO_Two H H H 2- (4-Me-BOxa) cHx 3-573 2-MeSO_Two H H H 2-BOxa -CH (Ph) Me 3-574 2-MeSO_Two H H H 3-BOxa 1-Et-Pn 3-575 2-MeSO_Two H H H 3-BOxa cHx 3-576 2-MeSO_Two H H H 3- (5-Me-BOxa) cHx 3-577 2-MeSO_Two H H H 3-BOxa -CH (Ph) Me 3-578 4-MeSO_Two H H H 2-BOxa 1-Et-Pn 3-579 4-MeSO_Two H H H 2-BOxa cHx 3-580 4-MeSO_Two H H H 2-BOxa -CH (Ph) Me 3-581 4-MeSO_Two H H H 3-BOxa 1-Et-Pn 3-582 4-MeSO_Two H H H 3-BOxa cHx 3-583 4-MeSO_Two H H H 3-BOxa -CH (Ph) Me 3-584 2-EtSO_Two H H H 2-BOxa 1-Et-Pn 3-585 2-EtSO_Two H H H 2-BOxa cHx 3-586 2-EtSO_Two H H H 2- (4-Me-BOxa) cHx 3-587 2-EtSO_Two H H H 2-BOxa -CH (Ph) Me 3-588 2-EtSO_Two H H H 3-BOxa 1-Et-Pn 3-589 2-EtSO_Two H H H 3-BOxa cHx 3-590 2-EtSO_Two H H H 3- (5-Me-BOxa) cHx 3-591 2-EtSO_Two H H H 3-BOxa -CH (Ph) Me 3-592 4-EtSO_Two H H H 2-BOxa 1-Et-Pn 3-593 4-EtSO_Two H H H 2-BOxa cHx 3-594 4-EtSO_Two H H H 2-BOxa -CH (Ph) Me 3-595 4-EtSO_Two H H H 3-BOxa 1-Et-Pn 3-596 4-EtSO_Two H H H 3-BOxa cHx 3-597 4-EtSO_Two H H H 3-BOxa -CH (Ph) Me 3-598 2-PhSO_Two H H H 2-BOxa tBu 3-599 2-PhSO_Two H H H 3-BOxa tBu 3-600 2- (4-Tol) SO_TwoHNOCHN H H H 2-BOxa -CH (Ph) Me 3-601 2- (4-Tol) SO_TwoHNOCHN HHH 3-BOxa -CH (Ph) Me 3-602 3-Tz HHH 2-BOxa -CH (4-Br-Ph) Me 3-603 4-Tz HHH 3-BOxa -CH (4-Br-Ph) Me . Also, in the above table, the bile acid transporter of the present invention
-Formula (I) contained as an active ingredient of the inhibitor
Compounds suitable for benzylamines having
Are the compound numbers 1-1, 1-3, 1-4, 1-5, 1-6, 1-87,
1-125, 1-176, 1-236, 1-266, 1-366, 1-367, 1-
410, 1-417, 1-418, 1-427, 1-442, 1-444, 1-44
7, 1-461, 1-467, 1-489, 1-503, 1-510, 1-518
 , 1-525,1-527,1-529,1-530,1-550,1-568
 , 1-572, 1-575, 1-586, 1-587, 1-593, 1-616
 , 1-617, 1-633, 1-637, 1-638, 1-639, 1-640
 , 1-641, 1-643, 1-654, 1-655, 1-665, 1-667
 , 1-669, 1-670, 1-675, 1-677, 1-679, 1-687
 , 1-696, 1-705, 1-707, 1-709, 1-710, 1-711
 , 1-712,1-767,1-768,1-769,1-771,1-775
 , 1-782, 1-784, 1-786, 1-802, 1-811, 1-815
 , 1-816, 1-820, 1-843, 1-847, 1-853, 1-873
 , 1-875, 1-876, 1-878, 1-879, 1-881, 1-884
 , 1-910, 1-927, 1-931, 1-945, 1-946, 1-952
 , 1-967, 1-968, 1-969, 1-972, 1-975, 1-994
 , 1-1014, 1-1019, 1-1028, 1-1035, 1-1051, 1-105
3, 1-1055, 1-1067, 1-1068, 1-1077, 1-1097, 1-111
0, 1-1133, 1-1135, 1-1138, 1-1150, 1-1153, 1-116
0, 1-1172, 1-1174, 1-1177, 1-1180, 1-1193, 1-119
5, 1-1196, 1-1202, 1-1219, 1-1220, 1-1222, 1-123
7, 1-1264, 1-1267, 1-1270, 1-1285, 1-1305, 1-131
8, 1-1346, 1-1387, 1-1392, 1-1400, 1-1409, 1-141
0, 1-1411, 1-1412, 1-1456, 1-1458, 1-1461, 1-147
7, 1-1512, 1-1522, 1-1609, 1-1645, 1-1649, 1-169
7, 1-1739, 1-1754, 1-1769, 1-1775, 1-1780, 1-178
2, 2-15, 2-18, 2-21, 2-24, 2-28, 2-31, 2-32, 2-9
4, 2-98, 2-119, 2-122, 2-131, 2-136, 2-140, 2
-144, 2-147, 2-152, 2-214, 2-220, 2-229, 2-2
42, 2-247, 2-248, 2-255, 2-260, 2-274, 2-276
 , 2-290, 2-297, 2-311, 2-315, 2-320, 2-339
 , 2-341, 2-344, 2-357, 2-360, 2-366, 2-375
 , 2-377, 2-399, 2-404, 2-405, 2-406, 2-408
 , 2-412, 2-422, 2-426, 2-447, 2-449, 2-454
 , 2-472, 2-499, 2-504, 3-7, 3-71, 3-77, 3-8
3, 3-86, 3-89, 3-90, 3-91, 3-100, 3-120, 3-132
 , 3-135, 3-141, 3-144, 3-153, 3-163, 3-165
 , 3-171, 3-173, 3-196, 3-201, 3-215, 3-223
 , 3-228, 3-237, 3-242, 3-243, 3-245, 3-250
 , 3-263, 3-270, 3-289, 3-298, 3-301, 3-306
 , 3-319, 3-323, 3-338, 3-344, 3-347, 3-352
 , 3-362, 3-374, 3-402, 3-410, 3-423, 3-437
 , 3-451, 3-453, 3-456, 3-464, 3-466, 3-470
 , 3-488, 3-510, 3-562 and 3-573
Compound No. is a more preferable compound.
1-410, 1-417, 1-427, 1-447, 1-489, 1-510, 1-
530,1-550,1-568,1-572,1-587,1-593,1-616
 , 1-617, 1-640, 1-669, 1-675, 1-677, 1-679,
1-687, 1-696, 1-711, 1-712, 1-786, 1-802, 1-
811, 1-815, 1-816, 1-820, 1-843, 1-847, 1-853
 , 1-879, 1-881, 1-884, 1-931, 1-945, 1-1019,
1-1035, 1-1077, 1-1097, 1-1133, 1-1135, 1-1138, 1-
1150, 1-1160, 1-1177, 1-1180, 1-1202, 1-1267, 1-14
11, 1-1412, 1-1461, 1-1512, 1-1522, 1-1645, 1-173
9, 1-1754, 2-15, 2-18, 2-21, 2-24, 2-242, 2-247,
2-255, 2-320, 2-344, 2-399, 2-404, 2-405, 2-
406, 2-408, 2-412, 2-422, 2-426, 2-449, 2-504
 , 3-7, 3-71, 3-77, 3-83, 3-89, 3-91, 3-141, 3-1
53, 3-223, 3-237, 3-242, 3-245, 3-298, 3-338
 , 3-344, 3-347, 3-402, 3-410, 3-423, 3-464
 , 3-488, 3-510, 3-562 and 3-573
Compound Nos. 1-417: N- (1-phenylethyl) -diff
Enyl- [6-hydroxy-4-methoxy-2- (1H
-Tetrazol-5-yl) phenyl] methyldiamido
Compound number 1-447: N- (1-ethylpentyl) -p
Enyl- [3- (1H-tetrazol-5-yl) fe
Nyl] methyldiamine, compound number 1-489: N- (1-phenylethyl) -diphenyl
Enyl- [3- (1H-tetrazol-5-yl) fe
Nyl] methyldiamine, compound number 1-530: N- (1-ethylpentyl) -diff
Enyl- [4- (1H-tetrazol-5-yl) fe
Nyl] methyldiamine, compound number 1-572: N- (1-phenylethyl) -diphenyl
Enyl- [4- (1H-tetrazol-5-yl) fe
Nyl] methyldiamine, Compound No. 1-587: N- (1-phenylethyl)-
{(4-methoxyphenyl)-[4- (1H-tetrazo
-Ru-5-yl) phenyl] methyl} amine, Compound No. 1-640: N- (1-phenylethyl)-[f
Enyl- (3-methylsulfonylcarbamoylphenyi)
L) methyl] amine, compound No. 1-679: N- (1-ethylpentyl)-[
Enyl- (3-N-tosylcarbamoylphenyl) methyl
Amine], compound No. 1-687: N-cyclohexyl- [phenyl-
(3-N-tosylcarbamoylphenyl) methyl] ami
Compound number 1-696: N- (1-phenylethyl)-[
Enyl- (3-N-tosylcarbamoylphenyl) methyl
Amine], compound No. 1-802: N- (1-phenylethyl) -diff
Enyl- [3- (2- (2-methylphenyl) phenyl)
Le) sulfonylcarbamoylphenyl] methyldiamido
Compound number 1-815: N- (1-phenylethyl) -d
Enyl- [3- (2- (3-methylphenyl) phenyl
Le) sulfonylcarbamoylphenyl] methyldiamido
Compound number 1-820: N- (1-phenylethyl) -d
Phenyl- [3- (2- (4-methylphenyl) phenyl]
Le) sulfonylcarbamoylphenyl] methyldiamido
Compound number 1-847: N- (1-phenylethyl) -d
Enyl- [4- (2- (2-methylphenyl) phenyl)
Le) sulfonylcarbamoylphenyl] methyldiamido
Compound No. 1-853: N- (1-phenylethyl) -d
Enyl- [4- (2- (4-methylphenyl) phenyl
Le) sulfonylcarbamoylphenyl] methyldiamido
Compound No. 1-1138: N- (1-ethylpentyl)-[f
Enyl- (2-ethylsulfonylphenyl) methyl] a
Min, Compound No. 1-1177: N- (indan-1-yl)-[f
Enyl- (2-ethylsulfonylphenyl) methyl] a
Compound No. 1-1180: N- (2-phenylethyl)-[
Enyl- (2-ethylsulfonylphenyl) methyl] a
Min, Compound No. 1-1512: N-tert-butyl- [phenyl
-(2-phenylsulfonylphenyl) methyl] ami
Compound No. 1-1739: N- ｛2- [1-phenyl-1-
(N-1-phenylethyl) amino] methyl @ phenyl
-N'-tosylurea, Compound No. 1-1754: N- {2- [1- (4-methoxyphenyl)
Enyl) -1- (N-1-phenylethyl) amino] me
N- (1-ethylpentyl)-{2-
Indenyl- [3- (1H-tetrazol-5-yl)
Phenyl] methyl} amine, Compound No. 2-24: N- (1-phenylethyl)-{2-
Indenyl- [4- (1H-tetrazol-5-yl)
Phenyl] methyl} amine, Compound No. 2-242: N- (1-ethylpentyl)-{1
-Naphthyl- [3- (1H-tetrazol-5-yl)
Phenyl] methyl} amine, Compound No. 2-247: N- (1-phenylethyl)-{1
-Naphthyl- [3- (1H-tetrazol-5-yl)
Phenyl] methyl} amine, Compound No. 2-255: N- (1-phenylethyl)-{1
-Naphthyl- [4- (1H-tetrazol-5-yl)
Phenyl] methyl} amine, compound number 3-223: N- [1- (4-bromophenyl)
Ethyl]-{(1,1-dioxothiophene-2-i
)-[3- (1H-tetrazol-5-yl) phenyl
[Methyl} amine, Compound No. 3-237: N- (1-ethylpentyl)-{2
-Thiazolyl- [3- (1H-tetrazol-5-i
L) phenyl] methyl} amine, compound number 3-242: N- (1-phenylethyl)-{3
-Thiazolyl- [3- (1H-tetrazol-5-i
L) phenyl] methyl} amine, compound number 3-298: N- (1-phenylethyl)-{2
-Indolyl- [3- (1H-tetrazol-5-i
L) phenyl] methyl} amine, compound number 3-338: N- [1- (4-bromophenyl)
Ethyl]-{2-indolyl- [3- (1H-tetrazo
-Ru-5-yl) phenyl] methyl} amine, compound number 3-423: N-cyclohexyl-[(1,1-
Dioxybenzothiophen-3-yl)-(2-methyl
Sulfonylphenyl) methyl] amine, Compound No. 3-464: N- [1- (4-bromophenyl)
Ethyl]-{(1,1-dioxybenzothiophene-2
-Yl)-[3- (1H-tetrazol-5-yl) phenyl
Enyl] methyldiamine, compound number 3-510: N- [1- (4-bromophenyl)
Ethyl]-{2-benzothiazolyl- [3- (1H-te
Trazol-5-yl) phenyl] methyldiamine and
And Compound No. 3-562: N- (1-phenylethyl)-{3
-Benzoxazolyl- [3- (1H-tetrazol-
5-yl) phenyl] methyl} amine.

[0090]

BEST MODE FOR CARRYING OUT THE INVENTION The compound having the general formula (I) of the present invention can be easily produced according to the following method.

[0091]

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[0092]

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[0093]

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In the above process, R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ in the chemical formulas described above have the same meanings as described above, and R ^2a , R ^3a and R ^4a Is the same as R ² , R ³ and R ⁴ except that the amino group contained in each group may be protected, and R ⁹ is a C ₁ -C ₆ alkyl group or a substituent Group β
C _6- which may be substituted by 1 to 3 groups selected from
A C ₁₀ aryl group, R ¹⁰ represents a C ₁ -C ₆ alkyl group, and Ar represents a C ₆ -C ₁₀ aryl group which may be substituted with one or two groups selected from the substituent group α. Tz
Represents a tetrazolyl group.

The amino-protecting group is not particularly limited as long as it is commonly used in the field of synthetic organic chemistry. Examples thereof include a t-butoxycarbonyl group; benzyl, methylbenzyl, methoxybenzyl, fluorobenzyl and chlorobenzyl. A benzyl group optionally substituted with C ₁ -C ₆ alkyl, C ₁ -C ₆ alkoxy or halogen; benzyloxycarbonyl, methylbenzyloxycarbonyl, methoxybenzyloxycarbonyl, fluorobenzyloxycarbonyl, chlorobenzyloxy A benzyloxycarbonyl group optionally substituted with C ₁ -C ₆ alkyl, C ₁ -C ₆ alkoxy or halogen such as carbonyl; or a halogenoacetyl group such as chloroacetyl, bromoacetyl, iodoacetyl; Suitably , T-butoxycarbonyl group, p
-Methoxybenzyl group, p-methoxybenzyloxycarbonyl group, chloroacetyl group, bromoacetyl group or iodoacetyl group, more preferably t-butoxycarbonyl group or p-methoxybenzyloxycarbonyl group, particularly preferred. Represents a t-butoxycarbonyl group.

Method A is a method for producing compound (I). Step A1 is a step of producing a compound having the general formula (V), and in an inert solvent, a compound having the general formula (III) and a compound having the general formula (IV) or an acid addition salt thereof (for example, hydrochloric acid). A mineral acid salt such as a salt, a nitrate or a sulfate), for example, a method of heat condensation using an organic sulfonic acid such as p-toluenesulfonic acid as a catalyst or a Lewis acid such as titanium tetrachloride. The condensation is carried out by using The inert solvent used in the above reaction is not particularly limited as long as it does not participate in the reaction. For example, hydrocarbons such as hexane, cyclohexane, benzene, toluene and xylene; dichloromethane, 1,2-dichloroethane Halogenated hydrocarbons such as carbon tetrachloride; alcohols such as methanol and ethanol; ether, tetrahydrofuran;
Ethers such as dioxane; ketones such as acetone; amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, hexamethylphosphoramide; dimethyl Sulfoxides such as sulfoxide; When heat condensation is carried out using an organic sulfonic acid as a catalyst, hydrocarbons (preferably xylene) are preferred. When the condensation is carried out using a Lewis acid, halogenated hydrocarbons (particularly preferably dichloromethane) are preferred.

In the above reaction, compound (IV)
Is a acid addition salt, the reaction can be carried out using a base. Such bases include, for example, organic amines such as triethylamine, N-methylmorpholine, pyridine, 4-dimethylaminopyridine; alkali metal bicarbonates such as sodium bicarbonate and potassium bicarbonate; sodium carbonate, potassium carbonate And an organic amine (particularly preferably, triethylamine).

The reaction temperature varies depending on the type of the starting compound, the base, the solvent and the like, but is usually from -20 ° C to 200 ° C. When heat condensation is carried out using an organic sulfonic acid as a catalyst, the temperature is preferably from 50 ° C to 150 ° C. The reaction time varies depending on the starting compound, the base, the solvent, the reaction temperature and the like, but is usually 15 minutes to 48 hours, preferably 1 hour to 30 hours.

After completion of the reaction, the target compound (V) of this reaction is collected from the reaction mixture according to a conventional method. For example, the reaction mixture is appropriately neutralized, and if insolubles are present, they are removed by filtration, an immiscible organic solvent such as water and ethyl acetate is added, and the organic layer containing the target compound is separated. After washing with water etc., drying with anhydrous magnesium sulfate etc.,
It is obtained by distilling off the solvent. If necessary, the obtained target compound is eluted with an appropriate eluent by applying a conventional method, for example, recrystallization, reprecipitation, etc., by appropriately combining the methods commonly used for separation and purification of organic compounds as appropriate and applying chromatography. Can be separated and purified.

The step A2 is a step of producing the compound (I), in which the compound (V) is reduced in an inert solvent, and then the amino-protecting group of the obtained compound is removed. The inert solvent used in the above reaction is not particularly limited as long as it does not participate in the reaction, and is, for example, the same as that used in the above-mentioned step A1, preferably alcohols or ethanol. -Tels (particularly preferably methano-
Or tetrahydrofuran). The reducing agent used in the above reaction is, for example, alkali metal borohydrides such as sodium borohydride, lithium borohydride, sodium cyanoborohydride; diisobutylaluminum hydride, lithium aluminum hydride, trihydride hydride. Aluminum hydride compounds such as lithium ethoxyaluminum; preferably alkali metal borohydrides (particularly preferably sodium cyanoborohydride).

The reaction temperature varies depending on the starting compound, the reducing agent used, the type of the solvent and the like, but is usually from -20 ° C to 150 ° C, preferably from 10 ° C to 80 ° C.
The reaction time varies depending on the starting compound, the reducing agent used, the solvent, the reaction temperature and the like, but is usually 15 minutes to 24 hours, preferably 30 minutes to 16 hours. After the above reaction, the protecting group for the amino group is removed by a method usually used in the field of organic synthetic chemistry. When the protecting group is a t-butoxycarbonyl group, a methoxybenzyl group or a methoxybenzyloxycarbonyl group, the corresponding compound is converted into an inert solvent (eg, ethers such as diethyl ether, tetrahydrofuran, dioxane, dichloromethane, 1, In halogenated hydrocarbons such as 2-dichloroethane, aromatic hydrocarbons such as benzene, toluene and xylene, preferably ethers, acids (for example, mineral acids such as hydrochloric acid, sulfuric acid and nitric acid); Acetic acid, trifluoroacetic acid, methanesulfonic acid, organic acid such as p-toluenesulfonic acid, preferably hydrochloric acid) and 0 ° C. to 50 ° C.
The protecting group is removed by reacting (preferably around room temperature) for 30 minutes to 5 hours (preferably 1 hour to 2 hours).

When the protecting group is a halogenoacetyl group, the corresponding compound is reacted with an inert solvent (for example, amides such as dimethylformamide and dimethylacetamide, sulfoxides such as dimethylsulfoxide, etc.).
Preferably, amides are combined with thiourea at 0 ° C to 50 ° C.
The protecting group is removed by reacting at 30 ° C. (preferably around room temperature) for 30 minutes to 5 hours (preferably 1 hour to 2 hours).

Further, when the protecting group is a benzyl group which may be substituted or a benzyloxycarbonyl group which may be substituted, the corresponding compound is converted into an inert solvent (for example, diethyl ether, tetrahydrofuran, dioxane). Hydrogen (preferably 1 to 3) in the presence of a catalytic reduction catalyst (eg, palladium-carbon, platinum oxide, etc.) in ethers such as Pressure)
And at 0 ° C. to 50 ° C. (preferably around room temperature) for 30 minutes to 10 hours (preferably 1 hour to 5 hours) to remove the protecting group.

After completion of the reaction, the target compound (I) of this reaction is collected from the reaction mixture according to a conventional method. For example, the reaction mixture is appropriately neutralized, and if insolubles are present, they are removed by filtration, an immiscible organic solvent such as water and ethyl acetate is added, and the organic layer containing the target compound is separated. After washing with water etc., drying with anhydrous magnesium sulfate etc.,
It is obtained by distilling off the solvent. If necessary, the obtained target compound is eluted with an appropriate eluent by applying a conventional method, for example, recrystallization, reprecipitation, etc., by appropriately combining the methods commonly used for separation and purification of organic compounds as appropriate and applying chromatography. Can be separated and purified.

[0105] Method B, in the compound (I), R ¹ is for producing a compound tetrazolyl group (Id) and the compound R ¹ is a C ₆ -C ₁₀ aryl group substituted with a tetrazolyl group (Ie) Is the way. Step B1 is a step of preparing a compound having the general formula (Id), in which a compound having the general formula (VI) is reacted with an azide compound in an inert solvent, and then protecting the amino group of the obtained compound. This is done by removing the group. The inert solvent used in the above reaction is not particularly limited as long as it does not participate in the reaction, for example, hexane, cyclohexane, benzene, toluene,
Hydrocarbons such as xylene; dichloromethane, 1,2
Halogenated hydrocarbons such as dichloroethane and carbon tetrachloride; ethers such as diethyl ether, tetrahydrofuran and dioxane; nitriles such as acetonitrile; N, N-dimethylformamide, N, N-dimethylacetamide; Amides such as methyl-2-pyrrolidone and hexamethylphosphoramide; sulfoxides such as dimethylsulfoxide; preferably hydrocarbons (particularly preferably toluene).

The azide compounds used in the above reaction include, for example, alkali metal azides such as lithium azide, sodium azide and potassium azide; alkaline earth metal azides such as magnesium azide and calcium azide; and trimethylsilyl azide. tri C ₁ -C ₆ alkylsilyl azides such; tri C ₁ -C ₆ alkyl tin azides such as trimethyltin azide; a is, preferably alkali metal azides (particularly preferably sodium azide)
It is. In the above reaction, the azide compound is used alone, and examples thereof include aluminum chloride, stannic chloride, tri-n-butyltin chloride, zinc chloride, titanium chloride, and trifluoroborane-diethyl ether complex. Lewis acids, ammonium salts such as ammonium chloride and tetramethylammonium chloride, sulfonic acids such as methanesulfonic acid and ethanesulfonic acid, alkali metal chlorides such as lithium chloride, and amine salts such as triethylamine hydrochloride. And preferably a Lewis acid (particularly preferably tri-n-butyltin chloride).

The reaction temperature varies depending on the starting compound, the azide compound used, the type of the solvent and the like, but is usually from 20 ° C. to 200 ° C. (preferably from 50 ° C. to 150 ° C.).
The reaction time varies depending on the starting compound, the azide compound used, the solvent, the reaction temperature and the like, but is usually 15 minutes to 24 hours (preferably 30 minutes to 16 hours). After the above reaction, the removal of the protecting group for the amino group is performed in the same manner as in the subsequent stage of the above-mentioned Method A, Step A2.

After completion of the reaction, the desired compound (Id) of the reaction is obtained.
Is collected from the reaction mixture according to a conventional method. For example,
The reaction mixture is appropriately neutralized, and if insolubles are removed by filtration, an immiscible organic solvent such as water and ethyl acetate is added, and the organic layer containing the target compound is separated. After drying with anhydrous magnesium sulfate etc.,
It is obtained by distilling off the solvent. If necessary, the obtained target compound is eluted with an appropriate eluent by applying a conventional method, for example, recrystallization, reprecipitation, etc., by appropriately combining the methods commonly used for separation and purification of organic compounds as appropriate and applying chromatography. Can be separated and purified.

Step B2 is a step of producing a compound having the general formula (Ie), and the step of preparing a compound of the general formula (VI) in an inert solvent
After reacting the compound having I) with the azide compound, the reaction is carried out by removing the protecting group for the amino group of the obtained compound, and this step is carried out in the same manner as the above-mentioned Method B, Step B1.

In the method C, in the compound (I), R ¹ is
C ₆ -C ₁₀ which may be substituted by 1 to 3 C ₁ -C ₆ alkylsulfonyl groups or a group selected from substituent group β.
A compound (If) which is an arylsulfonyl group, wherein R ¹ is C
_A compound (Ig) which is a C ₆ -C ₁₀ aryl group substituted with ₁ -C ₆ alkylsulfonyl, and R ¹ is C ₁ -C ₆
This is a method for producing a compound (Ih) which is an alkylsulfinyl group.

Step C1 is a step of producing a compound having the general formula (If), and the step of preparing a compound having the general formula (VII) in an inert solvent.
The reaction is carried out by reacting the compound having I) with an oxidizing agent, and then removing the amino-protecting group of the obtained compound. The solvent used in the above reaction is not particularly limited as long as it does not participate in the reaction, and examples thereof include aromatic hydrocarbons such as hexane, cyclohexane, benzene, toluene, and xylene; dichloromethane, 1,2-dichloroethane, Halogenated hydrocarbons such as carbon chloride; methanol,
Ethanol, n-propanol, isopropanol, n
Alcohols such as butanol, isobutanol and isoamyl alcohol; ethers such as ether, tetrahydrofuran, dioxane and dimethoxyethane; halogenated fatty acids such as trifluoroacetic acid;
Amides such as N, N-dimethylformamide, N, N-dimethylacetamide, hexamethyl phosphorotriamide; sulfoxides such as dimethyl sulfoxide; diluting acids such as sulfuric acid; diluting bases such as aqueous sodium hydroxide Ketones such as acetone and methyl ethyl ketone; organic bases such as pyridine; nitriles such as acetonitrile; water; and halogenated fatty acids (particularly preferably trifluoroacetic acid).

The oxidizing agent used in the above reaction is not particularly limited as long as it is used in a usual oxidation reaction. For example, manganese oxides such as potassium permanganate and manganese dioxide; ruthenium tetroxide Ruthenium oxides, such as selenium dioxide; iron compounds, such as iron chloride; osmium compounds, such as osmium tetroxide; silver compounds, such as silver oxide; mercury compounds, such as mercury acetate; And lead oxides such as lead tetraacetate; chromate compounds such as potassium chromate, chromate-sulfuric acid complex and chromate-pyridine complex; and inorganic metal oxides such as cerium compounds such as ammonium cerium nitrate (CAN) Agents; halogen molecules such as chlorine molecule, bromine molecule and iodine molecule; periodic acids such as sodium periodate;
Oxidizing gas such as ozone; nitrite such as nitrite; chlorite such as potassium chlorite and sodium chlorite; inorganic such as persulfate such as potassium persulfate and sodium persulfate Oxidizing agents; peroxides such as t-butyl hydroperoxide and hydrogen peroxide; organic peracids such as m-chloroperbenzoic acid (mCPBA) and peracetic acid; stable cations such as triphenylmethyl cation; Hypochlorous acid compounds such as t-butyl hypochlorite; nitrites such as methyl nitrite; quinone compounds such as 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) And organic peroxides such as peroxides or organic peracids (particularly preferably aqueous hydrogen peroxide or m-chloroperbenzoic acid).

The reaction temperature varies depending on the starting compound, the oxidizing agent to be used, the type of the solvent, and the like.
00 ° C. (preferably −10 ° C. to 50 ° C.). The reaction time varies depending on the starting compound, the oxidizing agent used, the solvent, the reaction temperature and the like, but is usually 15 minutes to 24 hours (preferably 30 minutes to 16 hours). After the above reaction, the removal of the protecting group for the amino group is performed in the same manner as in the subsequent stage of the above-mentioned Method A, Step A2.

After completion of the reaction, the desired compound (If)
Is collected from the reaction mixture according to a conventional method. For example,
The reaction mixture is appropriately neutralized, and if insolubles are removed by filtration, an immiscible organic solvent such as water and ethyl acetate is added, and the organic layer containing the target compound is separated. After drying with anhydrous magnesium sulfate etc.,
It is obtained by distilling off the solvent. If necessary, the obtained target compound is eluted with an appropriate eluent by applying a conventional method, for example, recrystallization, reprecipitation, etc., by appropriately combining the methods commonly used for separation and purification of organic compounds as appropriate and applying chromatography. Can be separated and purified.

Step C2 is a step of producing a compound having the general formula (Ig), and the step of preparing the compound of the general formula (IX) in an inert solvent
Is carried out by reacting a compound having the formula (I) with an oxidizing agent, and then removing the protecting group for the amino group of the obtained compound.

The step C3 is a step for producing a compound having the general formula (Ih). In the step C3, the compound having the general formula (X) is reacted with an oxidizing agent in an inert solvent. This step is performed by removing the protecting group of the group, and this step is performed in the same manner as in the above-mentioned Method C, Step C1.

The reaction temperature varies depending on the starting compound, the oxidizing agent to be used, the type of the solvent, and the like.
00 ° C. (preferably −20 ° C. to 10 ° C.), and the reaction time varies depending on the starting compound, the oxidizing agent used, the solvent, the reaction temperature and the like, but is usually 15 minutes to 12 hours (preferably, 15 minutes to 5 hours).

Starting compounds (III), (IV) and (V
I), (VII), (VIII), (IX) and (X) are known or are readily prepared according to known or analogous methods. [For example, Can. J. Che
m., 66, 1405 (1988), J. Chem. Soc., 352 (1949), Ch.
em. Abstr., 62, 11709 (1965), J. Am. Chem. Soc., 9
8, 2928 (1976), J. Org. Chem., 47, 34 (1982) and the like].

Further, starting compounds (III), (VI),
(VII), (VIII), (IX) and (X) are
It is also manufactured by the following method.

[0120]

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[0121]

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[0122]

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[0123]

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[0124]

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[0125]

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[0126]

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In the above formula, R ^2a , R ^3a , R ^4a , R ⁵ , R ⁶
And Ar have the same meaning as described above, and R ^2b , R ^3b
And R ^4b each represents an amino group in which the amino group contained in each group is protected, and R ² , R ³ and R ⁴
R ^5d represents a 2-thienyl, 2-pyrrolyl, 2-thiazolyl, 2-oxazolyl, 2-benzothienyl, 2-indolyl, 2-benzothiazolyl or 2-benzooxazolyl group; ¹¹ is C ₁ -C ₆
R ¹² represents a carboxy group, a cyano group,
R represents an amino group, a group having the formula —SR ⁹ , a group having the formula —SR ¹⁰ , or a C ₆ -C ₁₀ aryl group substituted with a carboxy, cyano or group having the formula —SR ¹⁰ ;
¹³ represents a C ₁ -C ₆ alkyl group or a C ₆ -C ₁₀ aryl group which may be substituted by 1 to 3 groups selected from a substituent group δ, and R ¹⁴ represents lithium, sodium, potassium or the like. R ¹⁵ represents a C ₆ -C ₁₀ aryl group which may be substituted by 1 to 3 groups selected from the substituent group β, and R ¹⁶ represents a C ₁ -C ₆ alkyl group. are shown, R ¹⁷ is a hydrogen atom or a C ₁ -C ₆ alkyl group, D is a halogen atom, Ar @ 1 was 1 to 3 substituted with a group selected from substituent group alpha C ₆ - It represents a C ₁₀ aryl group.

In Method D, compounds (VI), (VII),
Compound (X) comprising (VIII), (IX) and (X)
V). Step D1 is a compound (X)
In the step of producing III), a compound having the general formula (XI) is converted into a compound having the general formula (XI) in an inert solvent (preferably, hydrocarbons such as hexane, cyclohexane, benzene, toluene and xylene). The reaction is carried out by reacting the compound with -20 ° C to 200 ° C (preferably 0 ° C to 150 ° C) for 15 minutes to 24 hours (preferably 30 minutes to 16 hours).

Step D2 is a step of preparing a compound having the general formula (XIV), and converting the compound (XIII) into a compound (IV) or an acid addition salt thereof (eg, hydrochloride, nitrate, This step is performed in the same manner as in the above-mentioned Method A, Step A1.

Step D3 is a step for producing a compound having the general formula (XV), and the compound (XI) is prepared in an inert solvent.
V) is reduced, and this step is performed in the same manner as in the above-mentioned Method A, Step A2.

In step D4, compound (XIII) is converted to compound D
In a step separate from the one step, a compound having the general formula (XVI) is prepared by adding a compound having the general formula (XVI) in an inert solvent (preferably, hydrocarbons such as hexane, cyclohexane, benzene, toluene and xylene) to a base (preferably Is n-butyl lithium,
a compound having the general formula (XVII) in the presence of an organolithium such as t-butyllithium or phenyllithium) at -150 ° C to 50 ° C (preferably -100 ° C to 0 ° C) for 15 minutes to The reaction is carried out for 24 hours (preferably 30 minutes to 16 hours). The reaction can be carried out in the presence of an organic amine or the like (preferably N, N, N ', N'-tetramethylethylenediamine) in order to supplement the acid generated with the progress of the reaction.

In the method E, the compound represented by R ⁵
Is 2-thienyl, 2-pyrrolyl, 2-thiazolyl, 2
-Oxazolyl, 2-benzothienyl, 2-indolyl, 2-benzothiazolyl or a compound that is a compound that is a 2-benzoxazolyl group (XIIIa). Step E1 is a step of preparing a compound having the general formula (XVIII), and converting the compound (XI) in an inert solvent (preferably ethers such as diethyl ether, tetrahydrofuran, dioxane or triethylamine, N- Organic amines such as methylmorpholine, pyridine, 4-dimethylaminopyridine, 2,4,6-trimethylpyridine), a base (preferably triethylamine, N-methylmorpholine, pyridine, 4-dimethylaminopyridine, 2, In the presence or absence of organic amines such as 4,6-trimethylpyridine)
The reaction is carried out by reacting with hydroxypyridine at -20 ° C to 200 ° C (preferably 0 ° C to 150 ° C) for 15 minutes to 24 hours (preferably 30 minutes to 16 hours). The step E2 is a step of producing the compound (XIIIa), wherein the compound having the compound (XVIII) is
A compound having the general formula (XIX) in trifluoroacetic acid at -20 ° C to 200 ° C (preferably near the boiling point of trifluoroacetic acid) for 15 minutes to 24 hours (preferably 3
(0 minute to 16 hours).

[0133] Method F is, R ⁵ in the compound (XIII)
Is a method for producing a compound (XIIIb) wherein is a phenyl group. The step F1 is a step of producing a compound having the general formula (XIIIb), wherein the compound having the general formula (XI) is dissolved in an inert solvent (preferably, hexane, cyclohexane, benzene, toluene, xylene or the like). (Hydrocarbons) and benzene at −20 ° C. to 200 ° C. (preferably 0 ° C. to 150 ° C.) for 15 minutes to 24 hours (preferably 30 minutes to 20 hours). Compound (XI) is dissolved in an inert solvent (preferably, halogen hydrocarbons such as dichloromethane, 1,2-dichloroethane and carbon tetrachloride, and sulfoxides such as dimethyl sulfoxide), benzene and Lewis acids ( Preferably, it is also carried out by condensing with aluminum chloride, zinc chloride), at 20 ° C to 200 ° C.
(Preferably 50 ° C. to 150 ° C.) for 15 minutes to 24 hours
The reaction is carried out for a time (preferably 30 minutes to 16 hours).

In the method G, the compound (III) is treated with R ¹
Is a (C ₁ -C ₆ alkyl) sulfonylcarbamoyl group or a (C ₆ -C ₁₀ aryl) sulfonylcarbamoyl group which may be substituted by 1 to 3 groups selected from the group of substituents δ (IIIa) It is a method of manufacturing. The step G1 is a step of producing a compound having the general formula (IIIa), wherein the compound having the general formula (XIIIc) or a reactive derivative thereof is dissolved in an inert solvent (preferably, N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, amides such as hexamethylphosphoramide, sulfoxides such as dimethylsulfoxide), bases (preferably triethylamine, N-methylmorpholine, pyridine, 4
A compound having the general formula (XX) in the presence or absence of -dimethylaminopyridine, an organic amine such as 2,4,6-trimethylpyridine),
15 minutes to 2 hours at 50 ° C. (preferably 0 ° C. to 50 ° C.)
The reaction is carried out for 4 hours (preferably 30 minutes to 16 hours).

In the method H, the compound (III) is treated with R ¹
Is a (C ₆ -C ₁₀ aryl) sulfonylcarbamoylamino group (IIIb) which may be substituted by 1 to 3 groups selected from the substituent group β. Step H1 is a step of producing a compound having the general formula (IIIb), and a compound having the general formula (XIIId) in an inert solvent (preferably hexane, cyclohexane, benzene, toluene, xylene or the like). (Hydrocarbons) and a compound having the general formula (XXI) at 0 ° C. to 150 ° C. (preferably 0 ° C. to 50 ° C.) for 15 minutes to 24 hours (preferably 30 minutes to 16 hours). It is done by doing.

In the method I, the compound represented by R ¹
Is a C ₆ -C ₁₀ aryl group substituted by 1 to 3 groups selected from a substituent group α, and a compound (IIIc) in which R ² , R ³ and R ⁴ are hydrogen atoms. is there. Step I1 is a step for producing a compound having the general formula (IIIc), and a compound having the general formula (XIIIe) is dissolved in an inert solvent (preferably, hexane, cyclohexane, benzene, toluene, xylene or the like). Hydrocarbons, alcohols such as methanol and ethanol, water or a mixed solvent of the above solvents, and a base (preferably lithium carbonate, sodium carbonate and potassium carbonate) under a transition metal catalyst such as palladium hydroxide. A compound having the general formula (XXII) in the presence or absence of an alkali metal carbonate) under a nitrogen pressure, at -20 ° C to 200 ° C
The reaction is performed at (preferably 0 ° C. to 150 ° C.) for 15 minutes to 48 hours (preferably 30 minutes to 24 hours). This reaction can be carried out using a catalyst such as tetra-n-butylammonium.

In the method J, the compound (III) is treated with R ¹
Is a mono- (C ₁ -C ₆ alkyl) aminosulfonyl group or a di- (C ₁ -C ₆ alkyl) aminosulfonyl group (IIIe). Jth
One step is a step of producing a compound having the general formula (XXIII). A compound having the general formula (IIId) is prepared in an inert solvent (preferably dichloromethane, 1,2-dichloroethane, carbon tetrachloride or the like). Halogenated hydrocarbons), thionyl chloride, sulfuryl chloride, phosphorus oxychloride, phosphorus pentachloride, phosgene, chlorosulfonic acid, and -20 ° C to 200 ° C (preferably 0 ° C).
To 150 ° C.) for 15 minutes to 24 hours (preferably 3
(0 minute to 16 hours).

Step J2 is a step of producing compound (IIIe). Compound (XXIII) is treated with an inert solvent (preferably, hydrocarbons such as hexane, cyclohexane, benzene, toluene and xylene, dichloromethane). , 1,2-dichloroethane, halogen hydrocarbons such as carbon tetrachloride, ethers such as diethyl ether, tetrahydrofuran and dioxane), bases (preferably triethylamine, N-methylmorpholine, pyridine, 4-dimethylamino) (XXIV) or an acid addition salt thereof (preferably hydrochloride) in the presence or absence of pyridine, an organic amine such as 2,4,6-trimethylpyridine), at -20 ° C to 150 ° C. ° C (preferably,
The reaction is carried out at 0 ° C. to 100 ° C. for 15 minutes to 24 hours (preferably 30 minutes to 16 hours).

Method K is a method for producing compound (VI) separately from method D. The K1 step is a step of producing a compound having the general formula (XXV), and in an inert solvent, a compound having the general formula (XVa) or an acid addition salt thereof (eg, hydrochloride, nitrate, sulfate, etc.). (A mineral acid salt) or a reactive derivative thereof (acid halides, mixed acid anhydrides, active esters) and aqueous ammonia, for example, an acid halide method, a mixed acid anhydride method, an active ester method or This is performed by a condensation method. In the acid halide method, the compound (XVa) is reacted with a halogenating agent (eg, thionyl chloride, oxalic acid chloride, phosphorus pentachloride, etc.) to produce acid halides, and the acid halides and aqueous ammonia are added to an inert solvent. , In the presence or absence (preferably in the presence) of a base.

The inert solvent used in the above reaction is not particularly limited as long as it does not participate in the reaction.
Hydrocarbons such as hexane, cyclohexane, benzene, toluene and xylene; halogenated hydrocarbons such as dichloromethane, 1,2-dichloroethane and carbon tetrachloride; ethers such as diethyl ether, tetrahydrofuran and dioxane; acetonitrile Nitriles; amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, and hexamethylphosphoramide; sulfoxides such as dimethylsulfoxide; In
Ethers, nitriles, amides or sulfoxides (particularly preferably N, N-dimethylformamide).

The base used in the above reaction is, for example, triethylamine, N-methylmorpholine, pyridine,
Organic amines such as dimethylaminopyridine; alkali metal bicarbonates such as sodium hydrogencarbonate and potassium bicarbonate; alkali metal carbonates such as sodium carbonate and potassium carbonate; preferably organic amines ( Particularly preferred is triethylamine.

The reaction temperature varies depending on the type of the starting compound, the reagent, the solvent and the like, but the halogenating agent and compound (XVa)
Alternatively, the reaction with the acid addition salt thereof and the reaction between the acid halides and the aqueous ammonia are usually at -20 ° C to 150 ° C, preferably the reaction between the halogenating agent and the compound (XVa) or the acid addition salt thereof. Is −10 ° C. to 50 ° C., and the reaction between acid halides and aqueous ammonia is 0 ° C. to 100 ° C.
It is. The reaction time varies depending on the starting compound, the reagent, the solvent, the reaction temperature and the like.
Hours, preferably 30 minutes to 16 hours.

In the mixed acid anhydride method, the halogenocarbonate C ₁ -C
_6- alkyl, di-C ₁ -C ₆ alkyl cyanophosphoric acid or di-C ₆ -C ₁₀ arylphosphoryl azide is reacted with a compound (XVa) to produce mixed acid anhydrides. By reacting the compounds with aqueous ammonia. The reaction for producing mixed acid anhydrides is carried out by halogenocarbonate C ₁ -C ₆ alkyl such as ethyl chlorocarbonate and isobutyl chlorocarbonate; di-C ₁ -C ₆ alkyl such as dimethylcyanophosphate and diethylcyanophosphate. cyanophosphonate; or diphenylphosphoryl azide, is carried out by reacting di (p- nitrophenyl) phosphoryl azide, dinaphthyl phosphoryl di -C ₆ -C ₁₀ aryl azide with compounds such as azide (XVa), preferably Is carried out in an inert solvent in the presence of a base.

The base and the inert solvent used in the above reaction are the same as those used in the above-mentioned acid halide method. The reaction temperature varies depending on the type of the starting compound, the reagent, the solvent and the like, but is usually -20 ° C to 50 ° C, preferably 0 ° C to 30 ° C. The reaction time varies depending on the starting compound, the reagent, the solvent, the reaction temperature and the like.
Minutes to 24 hours, preferably 30 minutes to 16 hours.

The reaction between the mixed acid anhydrides and aqueous ammonia is carried out in an inert solvent in the presence or absence (preferably in the presence) of a base. And the same as those used in the above-mentioned acid halide method. The reaction temperature varies depending on the starting compound, the base used, the type of solvent, and the like, but is usually from -20 ° C to 100 ° C, and preferably from -10 ° C to 50 ° C. The reaction time varies depending on the starting compound, the base used, the solvent, the reaction temperature and the like, but is usually 15 minutes to 24 hours, preferably 30 minutes to 16 hours. Also, in the present method, the di-C ₁ -C ₆ alkyl cyanophosphoric acid or di-C _6
6 - ₁₀ when using an aryl azide is
Compound (XVa) can be directly reacted with aqueous ammonia in the presence of a base.

In the active ester method, the compound (XVa) is reacted with an active esterifying agent (for example, N-hydroxysuccinimide or N-hydroxybenzotriazole) in the presence of a condensing agent (for example, dicyclohexylcarbodiimide, carbonyldiimidazole, etc.). To obtain active esters, and reacting the active esters with aqueous ammonia. The reaction for producing the active esters is preferably carried out in an inert solvent, and the inert solvent used is the same as that used in the above-mentioned acid halide method. The reaction temperature varies depending on the type of the starting compound, reagent, solvent, etc.
In the active esterification reaction, it is usually −20 ° C. to 50 ° C., preferably -10 ° C. to 30 ° C., and in the reaction between the active ester compound and ammonia water, it is usually −20 ° C. to 50 ° C., Preferably, it is −10 ° C. to 30 ° C. The reaction time varies depending on the starting compound, the reagent, the solvent, the reaction temperature and the like, but is usually 15 minutes to 24 hours (preferably 30 minutes to 16 hours) for both reactions.

In the condensation method, a condensing agent (for example, dicyclohexylcarbodiimide, carbonyldiimidazole, 1-
In the presence of (N, N-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride or the like), the reaction is carried out by directly reacting the compound (XVa) with aqueous ammonia. This reaction is carried out in the same manner as the above-mentioned reaction for producing active esters.

Step K2 is a step of producing a compound having compound (VI), and in an inert solvent, compound (XX)
The reaction is performed by reacting V) with a dehydrating agent. The inert solvent used in the above reaction is not particularly limited as long as it does not participate in the reaction, and examples thereof include hydrocarbons such as hexane, cyclohexane, benzene, toluene and xylene; dichloromethane, 1,2-dichloroethane, and tetrachloromethane. Halogenated hydrocarbons such as carbon chloride; ethers such as diethyl ether, tetrahydrofuran and dioxane; nitriles such as acetonitrile; N, N-dimethylformamide, N, N-dimethylacetamide;
Amides such as -methyl-2-pyrrolidone and hexamethylphosphoramide; sulfoxides such as dimethylsulfoxide; preferably halogenated hydrocarbons (particularly preferably, dichloromethane).

The dehydrating agents used in the above reaction include, for example, phosphorus halide compounds such as phosphorus pentachloride, phosphorus oxychloride and phosphorus oxybromide; thionyl halide compounds such as thionyl chloride and thionyl bromide; Trifluoroacetic anhydride, methanesulfonyl chloride, p-toluenesulfonyl chloride, trifluoromethanesulfonic anhydride;
It is preferably a phosphorus halide compound (particularly preferably phosphorus oxychloride). The reaction temperature varies depending on the starting compound, the dehydrating agent used, the type of solvent, and the like, but is usually -20 ° C.
To 100 ° C (preferably -10 ° C to 50 ° C). The reaction time varies depending on the starting compound, the dehydrating agent used, the solvent, the reaction temperature and the like, but is usually 15 minutes to 24 hours (preferably 30 minutes to 16 hours).

Method L is a method for producing compound (VII) separately from method D. The step L1 is performed according to the general formula (XXV)
In the step of producing a compound having I), in an inert solvent,
A compound having the general formula (XVb) or an acid addition salt thereof (for example, a mineral acid salt such as hydrochloride, nitrate or sulfate) or a reactive derivative thereof (acid halides, mixed acid anhydride,
This step is carried out by reacting active esters) with aqueous ammonia, and this step is carried out in the same manner as the K method, the K1 step.

The step L2 is a step for producing a compound having the compound (VII), and the compound (XX) is prepared in an inert solvent.
This step is performed by reacting VI) with a dehydrating agent, and this step is performed in the same manner as in the K method, the K2 step.

After completion of the reaction, the target compound of each reaction is collected from the reaction mixture according to a conventional method. For example, the reaction mixture is appropriately neutralized, and if insolubles are present, they are removed by filtration, and then an immiscible organic solvent such as water and ethyl acetate is added, and the organic layer containing the target compound is separated. It is obtained by washing with water or the like, drying over anhydrous magnesium sulfate or the like, and then distilling off the solvent. The obtained target compound is used, if necessary, by a conventional method, for example, recrystallization, reprecipitation, etc., and appropriately combining a method commonly used for separation and purification of an organic compound,
It can be separated and purified by applying chromatography and eluting with a suitable eluent.

Starting compounds (XI), (XII) and (XV
I), (XVII), (XIX), (XX), (XX
I), (XXII) and (XXIV) are known or are easily produced by known methods. [For example,
Acta. Chim. Acad. Humg., 34, 75-76 (1962), Chem. Be.
r., 28, 1625 (1895), Chem. Abstr., 71, 123951j (19
69) etc.].

When the compound (I) of the present invention or a pharmacologically acceptable salt thereof is used as an ileal bile acid transporter inhibitor or a therapeutic or prophylactic agent for hyperlipidemia or arteriosclerosis. , By itself or mixed with an appropriate pharmacologically acceptable excipient or diluent, and administered orally by tablets, capsules, granules, powders or syrups, or parenterally by injection or the like. be able to.
These formulations include excipients (e.g., sugar derivatives such as lactose, sucrose, glucose, mannitol, sorbitol; starch derivatives such as corn starch, potato starch, alpha starch, dextrin; cellulose derivatives such as crystalline cellulose; Arabic gum; dextran; organic excipients such as pullulan: and silicate derivatives such as light anhydrous silicic acid, synthetic aluminum silicate, calcium silicate, magnesium metasilicate aluminate; phosphates such as calcium hydrogen phosphate; Inorganic excipients such as carbonates such as calcium; sulfates such as calcium sulfate; and lubricants (eg, metal stearate such as stearic acid, calcium stearate, magnesium stearate). Salt; Talc; Colloidal silica; Vegum, gay wax It waxes such as, boric acid; sulfates such as sodium sulfate; glycol adipic acid;
Fumaric acid; sodium benzoate; DL leucine; fatty acid sodium salt; lauryl sulfates such as sodium lauryl sulfate and magnesium lauryl sulfate; silicic acids such as silicic anhydride and silicic acid hydrate; it can. ), Binders (eg, hydroxypropylcellulose, hydroxypropylmethylcellulose,
Examples include polyvinylpyrrolidone, macrogol, and compounds similar to the above-mentioned excipients. ), Disintegrants (eg, cellulose derivatives such as low substituted hydroxypropylcellulose, carboxymethylcellulose, carboxymethylcellulose calcium, internally cross-linked sodium carboxymethylcellulose; chemically modified such as carboxymethyl starch, sodium carboxymethyl starch, cross-linked polyvinyl pyrrolidone) Starch and celluloses), stabilizers (paraoxybenzoic acid esters such as methylparaben and propylparaben; alcohols such as chlorobutanol, benzyl alcohol and phenylethyl alcohol; benzalkonium chloride; phenol Phenols such as cresol; thimerosal; dehydroacetic acid; and sorbic acid.), Flavoring agents (eg, Normally used sweeteners, acidulants, can be mentioned perfumes.), It is prepared in a known manner by using additives such as diluents.

The dosage varies depending on symptoms, age, etc., but in the case of oral administration, the lower limit is 1 mg (preferably 10 mg) per day, and the upper limit is 2000 mg (preferably 4 mg).
00mg), when administered intravenously, a lower limit of 0.1 mg (preferably 1 mg) per day and an upper limit of 500 mg (preferably 300 mg) per day may be administered to adults 1 to 6 times per day. It is desirable to administer according to.

[0156]

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

Example 1 N- (1-ethylpentyl)-{phenyl- [3- (1
[H-tetrazol-5-yl) phenyl] methyl} amine oxalate (Exemplified Compound No. 1-447) 143 mg of N- (1-ethylpentyl)-[phenyl- (3-cyanophenyl) methyl] amine was added. 2ml
Was dissolved in anhydrous toluene, and 43 mg of sodium azide and 0.19 ml of tri-n-butyltin chloride were added. The mixture was stirred at room temperature for 30 minutes, and then heated under reflux for 2 hours. 43 mg of sodium azide and 0.19 ml of tri-n-butyltin chloride were added to the reaction solution, and the mixture was heated under reflux for 2 hours. Then, 43 mg of sodium azide and 0.19 ml of tri-n-butyltin chloride were added and added for 1 hour Refluxed.
1.98 ml of 1N hydrochloric acid was added to the reaction solution, extracted with ethyl acetate, washed with saturated saline, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was separated and purified by silica gel column chromatography (elution solvent: cyclohexane / ethyl acetate = 1/1) to obtain 54 mg of a free form as colorless crystals.
mg of the title compound as an oxalate
mg. Melting point: 209-211 ° C. NMR spectrum (d ₆ -DMSO) δ ppm: 0.75-0.90 (6H, m),
1.10-1.35 (4H, m), 1.50-1.80 (4H, m), 2.60-2.75 (1H, m),
5.60 (1H, s), 7.30-8.00 (8H, m), 8.36 (1H, s).

Example 2 N- (1-ethylpentyl)-[phenyl- (2-methylsulfonylphenyl) methyl] amine hydrochloride (Exemplary Compound No. 1-884) (2a) N- (1-ethylpentyl)- [Phenyl-
(2-methylthiophenyl) methyl] amine 1.96 g of 2-methylthiobenzophenone and 1.96 g
g of 1-ethylpentylamine hydrochloride was dissolved in 46 ml of anhydrous dichloromethane, and stirred under ice-cooling under a nitrogen stream.
6.75 ml of triethylamine and 9.70 ml of a 1 molar solution of titanium tetrachloride dichloromethane were added and the reaction was stirred at room temperature for 17 hours. The reaction solution was diluted with ethyl acetate, washed with 0.5N hydrochloric acid and saturated saline,
After drying over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. The resulting residue was dissolved in 56 ml of methanol,
0.74 ml of acetic acid and 2.162 g of sodium cyanoborohydride were added, and the mixture was heated under reflux for 1 hour. The reaction solution was diluted with ethyl acetate, washed with saturated aqueous sodium hydrogen carbonate, water and brine, dried over anhydrous sodium sulfate, and dried under reduced pressure.
The solvent was distilled off. The obtained residue was separated and purified by silica gel column chromatography (elution solvent: cyclohexane / ethyl acetate = 9/1) to obtain 2.584 g of the desired product as a colorless oil. NMR spectrum (CDCl ₃ ) δ ppm: 0.80-0.95 (6H, m),
1.20-1.60 (9H, m), 2.35-2.45 (1H, m), 2.41 (3H, s), 5.46
(1H, s), 7.10-7.70 (9H, m).

(2b) N- (1-ethylpentyl)-
[Phenyl- (2-methylsulfonylphenyl) methyl] amine hydrochloride 0.59 m in 1.2 ml trifluoroacetic acid under ice salt cooling
Example 1 (2a) after dropwise addition of 1% of 30% aqueous hydrogen peroxide.
Compound N- (1-ethylpentyl)-[phenyl-
(2-methylthiophenyl) methyl] amine 618 mg
Is dissolved in 1.4 ml of trifluoroacetic acid and added dropwise,
Stirred overnight at room temperature. The reaction solution was neutralized by adding aqueous sodium bicarbonate,
After extraction with ethyl acetate, the extract was washed with brine, dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure.
The obtained residue was separated and purified by silica gel column chromatography (eluent: cyclohexane / ethyl acetate = 8/1) to give 383 mg of the title compound as a colorless oil.
After that, 338 mg of this colorless oil was obtained as a hydrochloride. Melting point: 180-182 ° C NMR spectrum (CDCl ₃ ) δ ppm: 0.75-0.95 (6H, m),
1.10-1.80 (8H, m), 2.68 (1.5H, s), 2.70-2.90 (1H, m), 3.
08 (1.5H, s), 6.96 (1H, br.s), 7.25-8.15 (8H, m), 8.65 (0.
5H, d, J = 7.9Hz), 8.73 (0.5H, d, J = 8.0Hz), 9.70-10.25 (2
H, br.s).

Example 3 N- (1-ethylpentyl)-[phenyl- (2-n-
[Butylsulfonylphenyl) methyl] amine oxalate (Exemplary Compound No. 1-1414) (3a) N- (1-ethylpentyl)-[phenyl-
(2-n-butylthiophenyl) methyl] amine 1.50 g of 2-n-butylthiobenzophenone and 1.
The reaction was carried out in the same manner as in Example (2a) using 68 g of 1-ethylpentylamine hydrochloride and purified to obtain 1.45 g of the title compound as a pale brown oil. NMR spectrum (CDCl ₃ ) δ ppm: 0.80-0.95 (9H, m),
1.15-1.70 (12H, m), 2.35-2.50 (1H, m), 2.75-2.90 (2H, m
m), 5.58 (1H, s), 7.10-7.70 (9H, m).

(3b) N- (1-ethylpentyl)-
[Phenyl- (2-n-butylsulfonylphenyl) methyl] amine oxalate N- (1-ethylpentyl)-[phenyl- (2-n-butylthiophenyl) methyl] amine of Example (3a) 25 g, 4.3 ml trifluoroacetic acid and 0.1 ml.
Using 96 ml of a 30% aqueous hydrogen peroxide solution, Example (2)
Reaction and purification were carried out in the same manner as in b) to give 1.33 g of the title compound as a pale yellow oil.
From 50 g, 353 mg as oxalate was obtained. Melting point: 143-145 ° C. NMR spectrum (CDCl ₃ ) δ ppm: 0.70-1.05 (9H, m),
1.00-1.95 (12H, m), 2.70-3.10 (3H, m), 6.71 (0.7H, s),
6.74 (0.3H, s), 7.30-8.10 (9H, m).

Example 4 N-cyclohexyl- [phenyl- (2-methylsulfonylphenyl) methylamine (Exemplified Compound No. 1-90)
6) (4a) N-cyclohexyl- [phenyl- (2-methylthiophenyl) methyl] amine 2.0 g of 2-methylthiobenzophenone and 3.02 m
Using 1 of cyclohexylamine, the reaction was carried out in the same manner as in Example (2a) and purified to obtain 228 mg of the title compound as a yellow oil. NMR spectrum (CDCl ₃ ) δ ppm: 1.00-1.30 (5H, m),
1.40-2.05 (6H, m), 2.30-2.45 (1H, m), 2.42 (3H, s), 5.51
(1H, s), 7.10-7.60 (9H, m).

(4b) N-cyclohexyl- [phenyl- (2-methylsulfonylphenyl) methyl] amine N-cyclohexyl- [phenyl-] of Example (4a)
(2-Methylthiophenyl) methyl] amine 228m
g, 2.38 ml of trifluoroacetic acid and 0.46 m
The reaction was carried out in the same manner as in Example (2b) using 1 l of a 30% aqueous hydrogen peroxide solution and purified to obtain 65 mg of the title compound as colorless crystals. Melting point: 105-107 ° C NMR spectrum (CDCl ₃ ) δ ppm: 0.95-1.30 (5H, m),
1.45-2.10 (6H, m), 2.38-2.53 (1H, m), 2.78 (3H, s), 6.32
(1H, s), 7.20-8.10 (9H, m).

Example 5 N-cyclohexyl- [phenyl- (2-n-butylsulfonylphenyl) methyl] amine hydrochloride (Exemplary Compound No. 1-1436) (5a) N-cyclohexyl- [phenyl- (2-n-
Butylthiophenyl) methyl] amine 2.0 g of 2-n-butylthiobenzophenone and 1.7
Example 2a using ml of cyclohexylamine
And purified to give 2.49 g of the title compound as a pale brown oil. NMR spectrum (CDCl ₃ ) δ ppm: 0.90 (3H, t, J = 7.3H)
z), 1.00-1.28 (5H, m), 1.30-1.75 (8H, m), 1.85-2.05 (2H,
m), 2.30-2.48 (1H, m), 2.75-2.90 (2H, m), 5.63 (1H, s),
7.10-7.60 (9H, m).

(5b) N-cyclohexyl- [phenyl- (2-n-butylsulfonylphenyl) methyl] amine hydrochloride N-cyclohexyl- [phenyl-] of Example (5a)
(2-n-butylthiophenyl) methyl] amine 1.4
9 g, 5.8 ml of trifluoroacetic acid and 1.3 ml
The reaction was carried out in the same manner as in Example (2b) using a 30% aqueous hydrogen peroxide solution and purified to obtain a hydrochloride, thereby obtaining 1.59 g of the title compound as colorless crystals. Melting point: 266-269 ° C. NMR spectrum (CDCl ₃ ) δ ppm: 0.73 (3H, t, J = 7.3H)
z), 0.80-1.75 (12H, m), 1.85-1.98 (1H, m), 2.15-2.28 (1
H, m), 2.55-2.80 (3H, m), 6.99 (1H, s), 7.25-7.80 (7H,
m), 8.05 (1H, d, J = 8.0Hz), 8.70 (1H, d, J = 7.9Hz).

Example 6 N-cyclohexyl- [phenyl- (2-n-butylsulfinylphenyl) methyl] amine oxalate (Exemplified Compound No. 1-1645) N-cyclohexyl- [phenyl-] of Example (5a)
(2-n-butylthiophenyl) methyl] amine 283
mg was dissolved in 3.0 ml of trifluoroacetic acid, 0.08 ml of 30% aqueous hydrogen peroxide was added under ice cooling, and the mixture was stirred for 30 minutes. The reaction solution was neutralized with sodium bicarbonate and extracted with ethyl acetate. The extract was washed with saturated saline, dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was separated and purified by silica gel column chromatography (elution solvent: cyclohexane / ethyl acetate = 9/1) to give 212 mg.
Oil was obtained. Using this colorless oil as oxalate,
188 mg of the title compound was obtained as colorless crystals. Melting point: 166-168 ° C (decomposition) NMR spectrum (CDCl ₃ ) δppm: 0.77 (3H, t, J = 7.3H)
z), 0.90-2.00 (14H, m), 2.25-2.40 (2H, m), 2.75-2.95 (2
H, m), 5.99 (1H, s), 7.20-8.30 (9H, m).

Example 7 N-cyclohexyl- [phenyl- (4-methylsulfonylphenyl) methyl] amine oxalate (Exemplary Compound No. 1-10777) (7a) N-cyclohexyl- [phenyl- (4-methylthiophenyl) Methyl] amine 1.0 g of 4-methylthiobenzophenone and 1.01 m
Using 1 of cyclohexylamine, the reaction was carried out in the same manner as in Example (2a) and purified to obtain 812 mg of the title compound as a pale pink oil. NMR spectrum (CDCl ₃ ) δ ppm: 1.00-1.25 (5H, m),
1.40-2.00 (6H, m), 2.30-2.45 (1H, m), 2.45 (3H, s), 4.99
(1H, s), 7.10-7.40 (9H, m).

(7b) N-cyclohexyl- [phenyl- (4-methylsulfonylphenyl) methyl] amine oxalate N-cyclohexyl- [phenyl-amine of Example (7a)
(4-methylthiophenyl) methyl] amine 517 mg
And 5.1 ml of trifluoroacetic acid and 1.1 ml of 30%
The reaction was carried out in the same manner as in Example (2b) using aqueous hydrogen peroxide, and the mixture was purified. The title compound was obtained as colorless crystals (426 mg).
Obtained. Melting point: 106 ° C. (decomposition) NMR spectrum (CDCl ₃ ) δ ppm: 0.90-1.30 (5H, m),
1.50-2.00 (5H, m), 2.80- 2.95 (1H, m), 3.01 (3H, s), 5.6
7 (1H, s), 7.30-7.95 (9H, m).

Example 8 N-isopropyl- [phenyl- (2-n-butylsulfonylphenyl) methyl] amine oxalate (Exemplary Compound No. 1-1409) (8a) N-isopropyl- [phenyl- (2-n) -Butylthiophenyl) methyl] amine 1.0 g of 2-n-butylthiobenzophenone and 0.6 g
Example (2a) using 3 ml of isopropylamine
And 950 mg of the title compound as a pale brown oil. NMR spectrum (CDCl ₃ ) δ ppm: 0.90 (3H, t, J = 7.3H)
z), 1.09 (6H, d, J = 6.3Hz), 1.30-1.70 (5H, m), 2.70-2.90
(3H, m), 5.57 (1H, s), 7.10-7.55 (9H, m).

(8b) N-isopropyl- [phenyl-
(2-n-butylsulfonylphenyl) methyl] amine oxalate N-isopropyl- [phenyl- (2
-N-butylthiophenyl) methyl] amine 427 m
g, 4.76 ml of trifluoroacetic acid and 0.92 m
Using 1 l of a 30% aqueous hydrogen peroxide solution, the reaction was carried out in the same manner as in Example (2b), followed by purification to obtain 159 mg of the title compound as colorless crystals as oxalate. Melting point: 158-160 ° C NMR spectrum (CDCl ₃ ) δppm: 0.73 (3H, t, J = 7.3H)
z), 1.00-1.70 (4H, m), 1.20 (3H, d, J = 6.3Hz), 1.31 (3H, d,
J = 6.3Hz), 2.55-2.80 (2H.m), 3.20-3.45 (1H, m), 6.81 (1
H, s), 7.30-8.40 (9H, m).

Example 9 N-tert-butyl- [phenyl- (2-n-butylsulfonylphenyl) methyl] amine (Exemplary Compound No. 1-1141) (9a) N-tert-butyl- [phenyl- (2- n
-Butylthiophenyl) methyl] amine 1.0 g of 2-n-butylthiobenzophenone and 0.7 g
Example 7 (2) using 7 ml of tert-butylamine
The reaction was carried out in the same manner as in a), followed by purification to obtain 326 mg of the title compound as a yellow oil. NMR spectrum (CDCl ₃ ) δ ppm: 0.89 (3H, t, J = 7.3H)
z), 1.07 (9H, s), 1.30-1.65 (5H, m), 2.70-2.90 (2H, m),
5.61 (1H, s), 7.10-7.40 (8H, m), 7.88 (1H, d, J = 7.2Hz)
.

(9b) N-tert-butyl- [phenyl- (2-n-butylsulfonylphenyl) methyl] amine N-tert-butyl- [phenyl-amine of Example (9a)
(2-n-butylthiophenyl) methyl] amine 185
mg, 3.0 ml of trifluoroacetic acid and 0.42 m
The reaction was carried out in the same manner as in Example (2b) using 1 l of a 30% aqueous hydrogen peroxide solution and purified to obtain 115 mg of the title compound as colorless columnar crystals. Melting point: 74-76 ° C NMR spectrum (CDCl ₃ ) δppm: 0.62 (3H, t, J = 7.2H)
z), 0.75-1.05 (2H, m), 1.08 (9H, s), 1.35-1.58 (3H, m),
2.20-2.50 (2H, m), 6.39 (1H, s), 7.12-7.30 (5H, m), 7.40
-7.48 (1H, m), 7.67-7.75 (1H, m), 7.95 (1H, d, J = 7.9Hz),
8.61 (1H, d, J = 7.9Hz).

Example 10 N-neopentyl- [phenyl- (2-n-butylsulfonylphenyl) methyl] amine oxalate (Exemplary Compound No. 1-1412) (10a) N-neopentyl- [phenyl- (2-n) −
Butylthiophenyl) methyl] amine 500 mg of 2-n-butylthiobenzophenone and 0.1 mg
Example (2) using 44 ml of neopentylamine
The reaction was carried out in the same manner as in a), followed by purification to obtain 520 mg of the title compound as a pale brown oil. NMR spectrum (CDCl ₃ ) δ ppm: 0.80-1.00 (12H, m),
1.35-1.70 (5H, m), 2.34 (2H, s), 2.75-2.95 (2H, m), 5.33
(1H, s), 7.10-7.55 (9H, m).

(10b) N-neopentyl- [phenyl- (2-n-butylsulfonylphenyl) methyl] amine oxalate N-neopentyl- [phenyl-] of Example (10a)
(2-n-butylthiophenyl) methyl] amine 520
mg, 2.0 ml trifluoroacetic acid and 0.4 ml
The reaction was carried out in the same manner as in Example (2b) using 30% aqueous hydrogen peroxide to give 533 mg of a colorless oil. The title compound was converted into colorless crystals from 276 mg of this oil.
81 mg were obtained. Melting point: 155-157 ° C NMR spectrum (CDCl ₃ ) δppm: 0.91 (3H, t, J = 7.3H)
z), 1.07 (9H, s), 1.27-1.95 (4H, m), 2.80 (2H, dd, J = 12.0
Hz, J = 7.3Hz), 2.95-3.30 (2H, m), 6.18 (1H, s), 7.40-7.7
5 (8H, m), 8.00 (1H, d, J = 7.1Hz).

Example 11 N-cyclohexyl-[(1,1-dioxybenzothiophen-3-yl)-(2-methylsulfonylphenyl) methyl] amine (Exemplified Compound No. 3-423) (11a) N-cyclohexyl -[(Benzothiophen-3-yl)-(2-methylthiophenyl) methyl] amine 397 mg of (benzothiophene-
3-yl)-(2-methylthiophenyl) ketone and 0.1.
Using 96 ml of cyclohexylamine, Example (2)
The reaction was carried out in the same manner as in a) to obtain 346 mg of the title compound as a yellow oil. NMR spectrum (CDCl ₃ ) δ ppm: 1.00-1.80 (9H, m),
1.90-2.15 (2H, m), 2.43 (3H, s), 2.50-2.65 (1H, m), 5.88
(1H, s), 7.05-7.90 (9H, m).

(11b) N-cyclohexyl-[(1,
1-dioxybenzothiophen-3-yl)-(2-methylsulfonylphenyl) methyl] amine N-cyclohexyl-[(benzothiophen-3-yl)-(2-methylthiophenyl) methyl] of Example (11a) The reaction was carried out in the same manner as in Example (2b) using 346 mg of amine, 5.0 ml of trifluoroacetic acid and 0.5 ml of 30% aqueous hydrogen peroxide to obtain 115 mg of the title compound as colorless crystals. Melting point: 147-150 ° C NMR spectrum (d ₆ -DMSO) δppm: 0.95-1.25 (5H, m),
1.45-2.05 (5H, m), 2.40-2.55 (1H, m), 2.91 (1H, d, J = 11.2
Hz), 3.35 (3H, s), 6.32 (1H, d, J = 11.1Hz), 6.96 (1H, s),
7.55-7.90 (7H, m), 8.05 (1H, d, J = 7.6Hz).

Example 12 (12-1) N-cyclohexyl- [2-thienyl-
(2-Methylsulfinylphenyl) methyl] amine oxalate (Exemplary Compound No. 3-144) and (12-2) N-cyclohexyl- [2-thienyl-
(2-Methylsulfonylphenyl) methyl] amine oxalate (Exemplary Compound No. 3-100) (12a) N-cyclohexyl- [2-thienyl- (2
-Methylthiophenyl) methyl] amine 455 mg of (2-thienyl) -2 obtained in Reference Example 2.
-Methylthiophenyl ketone and 0.89 ml of cyclohexylamine were reacted in the same manner as in Example (2a) and purified to give the title compound as a pale yellow oil (435).
mg. NMR spectrum (CDCl ₃ ) δppm: 1.03-1.3
0 (5H, m), 1.50-1.80 (4H, m), 1.85-2.10 (2H, m), 2.35-2.
55 (1H, m), 2.45 (3H, s), 5.77 (1H, s), 6.80-6.95 (2H, m),
7.10-7.30 (4H, m), 7.54 (1H, d, J = 6.8Hz).

(12b-1) N-cyclohexyl- [2
-Thienyl- (2-methylsulfinylphenyl) methyl] amine oxalate and (12b-2) N-cyclohexyl- [2-thienyl-
(2-Methylsulfonylphenyl) methyl] amine oxalate N-cyclohexyl- [2-thienyl- (2-methylthiophenyl) methyl] amine 435 of Example (12a)
mg was dissolved in 3.0 ml of trifluoroacetic acid, 0.26 ml of 30% aqueous hydrogen peroxide was added under ice salt cooling and stirring, and the mixture was stirred under ice salt cooling for 45 minutes. The mixture was neutralized with saturated aqueous sodium hydrogen carbonate, extracted with ethyl acetate, dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was separated and purified by silica gel column chromatography (elution solvent: dichloromethane / ethyl acetate = 2/1) to obtain 52 mg of a first outflow portion. When this was used as the oxalate, the title compound of (12b-2) was obtained as colorless crystals.
9 mg was obtained. The next outflow was 387 mg. Using this 387 mg as an oxalate, 411 mg of the title compound of (12b-1) was obtained as colorless crystals. (12b-
1) Melting point: 138-143 ° C. NMR spectrum (d ₆ -DMSO) δ ppm: 0.95-1.30 (5H, m),
1.40-2.05 (5H, m), 4.41 (2H, s), 2.79 (1H, s), 5.76 (0.33
H, s), 5.79 (0.67H, s), 6.90-8.00 (7H, m). (12b-
2) Melting point: 184 ° C. (decomposition) NMR spectrum (d ₆ -DMSO) δ ppm: 1.00-1.30 (5H, m),
1.40-2.05 (5H, m), 2.45-2.60 (1H, m), 3.14 (3H, s), 6.53
(1H, s), 6.95-7.10 (2H, m), 7.50 (1H, d, J = 4.9Hz), 7.61
(1H, t, J = 7.5Hz), 7.81 (1H, t, J = 7.3Hz), 7.98 (1H, d, J = 8.
0Hz), 8.06 (1H, d, J = 7.8Hz).

Example 13 N-cyclohexyl- [phenyl- (2-phenylsulfonylphenyl) methyl] amine (Exemplified Compound No. 1-
1522) (13a) N-cyclohexyl- [phenyl- (2-phenylthiophenyl) methyl] amine 500 mg of 2-phenylthiobenzophenone and 0.4
Example 2a using ml of cyclohexylamine
And 620 mg of the title compound was obtained as a pale yellow oil. NMR spectrum (CDCl ₃ ) δppm: 0.90-1.25 (5H, m),
1.40-2.00 (6H, m), 2.25-2.42 (1H, m), 5.67 (1H, s), 7.10
-7.70 (14H, m).

(13b) N-cyclohexyl- [phenyl- (2-phenylsulfonylphenyl) methyl] amine N-cyclohexyl- [phenyl-amine of Example (13a)
(2-phenylthiophenyl) methyl] amine 500 m
g, 2.0 ml of trifluoroacetic acid and 0.77 ml of 3
The reaction was carried out in the same manner as in Example (2b) using 0% aqueous hydrogen peroxide and purified.
mg. Melting point: 96-98 ° C NMR spectrum (CDCl ₃ ) δppm: 0.80-1.20 (5H, m),
1.35-1.85 (6H, m), 2.10-2.28 (1H, m), 5.86 (1H, m), 6.98
-7.20 (5H, m), 7.35-7.70 (5H, m), 7.75-7.90 (3H, m), 8.2
0 (1H, d, J = 7.9Hz).

Example 14 N-Cyclohexyl- [phenyl- (2-ethylsulfonylphenyl) methyl] amine (Exemplified Compound No. 1-1)
160) (14a) N-cyclohexyl- [phenyl- (2-ethylthiophenyl) methyl] amine Using 0.50 g of 2-ethylthiobenzophenone obtained in Reference Example 6 and 0.5 ml of cyclohexylamine The reaction was carried out in the same manner as in Example (2a) and purified to obtain 0.75 g of the title compound as a tan oil. NMR spectrum (CDCl ₃ ) δ ppm: 1.00-1.25 (5H, m),
1.28 (3H, t, J = 7.4Hz), 1.45-1.78 (4H, m), 1.88-2.18 (2H,
m), 2.30-2.45 (1H, m), 2.80-2.95 (2H, m), 5.62 (1H, s),
7.12-7.55 (9H, m).

(14b) N-cyclohexyl- [phenyl- (2-ethylsulfonylphenyl) methyl] amine N-cyclohexyl- [phenyl-amine of Example (14a)
(2-ethylthiophenyl) methyl] amine 0.50
g, 2.0 ml of trifluoroacetic acid and 0.87 ml
The reaction was carried out in the same manner as in Example (2b) using 30% aqueous hydrogen peroxide and purified to obtain 0.38 g of the title compound as colorless crystals. Melting point: 93-94 ° C NMR spectrum (CDCl ₃ ) δppm: 0.90-1.25 (8H, m),
1.40-2.08 (6H, m), 2.38-2.50 (1H, m), 2.73-2.95 (2H, m),
6.29 (1H, s), 7.20-7.50 (6H, m), 7.60-7.70 (1H, m), 7.9
3 (1H, d, J = 6.9Hz), 8.02 (1H, dd, J = 1.2Hz, J = 7.9Hz).

Example 15 N-benzyl- [phenyl- (2-ethylsulfonylphenyl) methyl] amine hydrochloride (Exemplified Compound No. 1-1)
178) (15a) N-benzyl- [phenyl- (2-ethylthiophenyl) methyl] amine Performed using 0.50 g of 2-ethylthiobenzophenone obtained in Reference Example 6 and 0.45 ml of benzylamine. The reaction was carried out and purified in the same manner as in Example (2a), to give 0.66 g of the title compound as a pale yellow oil. NMR spectrum (CDCl ₃ ) δppm: 1.26 (3H, t, J = 7.3H
z), 2.84 (2H, q, J = 7.3Hz), 3.75 (2H, s), 5.48 (2H, s), 7.
15-7.65 (14H, m).

(15b) N-benzyl- [phenyl-
(2-ethylsulfonylphenyl) methyl] amine hydrochloride N-benzyl- [phenyl- (2-
0.50 g of ethylthiophenyl) methyl] amine;
0 ml of trifluoroacetic acid and 0.83 ml of 30%
The reaction was carried out in the same manner as in Example (2b) using aqueous hydrogen peroxide, and the mixture was purified. 0.48 g of the title compound was obtained as colorless crystals.
Obtained. Melting point: 247-248 ° C (decomposition) NMR spectrum (CDCl ₃ ) δppm: 1.09 (3H, t, J = 7.3H)
z), 2.50-2.85 (2H, m), 3.70-4.15 (2H, m), 6.39 (1H, d, H =
6.1Hz), 7.25-7.70 (10H, m), 7.85-8.10 (3H, m), 8.51 (1H,
d, J = 7.8Hz), 10.60-11.20 (2H, br.s).

Example 16 N-trans-4-methoxycarbonylcyclohexylmethyl- [phenyl- (2-ethylsulfonylphenyl) methyl] amine oxalate (Exemplified Compound No. 1-1)
175) (16a) N-trans-4-methoxycarbonylcyclohexylmethyl- [phenyl- (2-ethylthiophenyl) methyl] amine 1.50 g of 2-ethylthiobenzophenone obtained in Reference Example 6 and 2.60 g of Example (2) using trans-4-methoxycarbonylcyclohexylmethylamine
The reaction was carried out in the same manner as in a), followed by purification to obtain 2.32 g of the title compound as a pale yellow oil. NMR spectrum (CDCl ₃ ) δppm: 0.85-1.05 (2H, m),
1.29 (3H, t, J = 7.5Hz), 1.30-1.65 (4H, m), 1.82-2.05 (4H,
m), 2.15-2.30 (1H, m), 2.44 (2H, d, J = 6.6Hz), 2.88 (2H, q,
J = 7.4Hz), 3.66 (3H, s), 5.34 (1H, s), 7.10-7.53 (9H, m)
.

(16b) N-trans-4-methoxycarbonylcyclohexylmethyl- [phenyl- (2-ethylsulfonylphenyl) methyl] amine oxalate N-trans-4-methoxycarbonylcyclohexylmethyl- of Example (16a) The reaction was carried out in the same manner as in Example (2b) using 2.0 g of [phenyl- (2-ethylthiophenyl) methyl] amine, 8.0 ml of trifluoroacetic acid and 2.9 ml of 30% aqueous hydrogen peroxide, Purification gave 1.83 g of a colorless oil. From 0.2 g of the oil, 0.15 g of the title compound was obtained as colorless crystals. Melting point: 132-134 ° C NMR spectrum (CDCl ₃ ) δppm: 0.80-1.05 (2H, m),
1.14 (3H, t, J = 7.4Hz), 1.30-1.65 (4H, m), 2.15-2.30 (1H,
m), 2.38 (1H, dd, J = 6.8Hz, J = 11.3Hz), 2.55 (1H, dd, J = 6.2
Hz, J = 11.3Hz), 2.80-3.05 (2H, m), 3.65 (3H, s), 5.94 (1
H, s), 7.20-7.50 (6H, m), 7.55-7.65 (1H, m), 7.77 (1H, d,
J = 6.9Hz), 8.02 (1H, dd, J = 1.2Hz, J = 7.9Hz).

Example 17 N-4-methylcyclohexyl- [phenyl- (2-n
-Butylsulfonylphenyl) methyl] amine oxalate (Exemplary Compound No. 1-1442) (17a) N-4-methylcyclohexyl- [phenyl- (2-n-butylthiophenyl) methyl] amine 500 mg of 2-n- Butylthiobenzophenone and 0.1.
Using 49 ml of 4-methylcyclohexylamine,
The reaction and purification were conducted in the same manner as in Example (2a), and the two title compounds were converted into pale yellow oily intermediates (17a-1).
227 mg and 104 mg of the intermediate (17a-2) were obtained. (17a-1) Rf = 0.7 (developing solvent: cyclohexane / ethyl acetate = 9/1) NMR spectrum (CDCl ₃ ) δppm: 0.80-1.00 (6H, m),
1.20-1.75 (14H, m), 2.60-2.70 (1H, m), 2.75-2.90 (2H,
m), 5.54 (1H, s), 7.13-7.60 (9H, m). (17a-2) Rf = 0.5 (developing solvent: cyclohexane / ethyl acetate = 9/1) NMR spectrum (CDCl ₃ ) δ ppm: 0.83 (3H, d, J = 6.5H)
z), 0.90 (3H, t, J = 7.3Hz), 1.00-1.75 (12H, m), 1.93-2.1
0 (2H, m), 2.26-2.40 (1H, m), 2.78-2.90 (2H, m), 5.63 (1
H, s), 7.10-7.60 (9H, m).

(17b-1) N-4-methylcyclohexyl- [phenyl- (2-n-butylsulfonylphenyl) methyl] amine oxalate Intermediate (17a-1) 211 mg, 3.0 ml of trifluoroacetic acid and The reaction was carried out in the same manner as in Example (2b) using 0.5 ml of a 30% aqueous hydrogen peroxide solution, purified, and further converted to an oxalate salt. The title compound was converted into colorless crystals by 174.
mg. Melting point: 202-204 ° C NMR spectrum (d ₆ -DMSO) δppm: 0.71 (3H, t, J = 7.3H)
z), 0.89 (3H, d, J = 6.7Hz), 1.05-1.80 (13H, m), 2.62-2.7
8 (1H, m), 2.90-3.15 (2H, m), 6.34 (1H, s), 7.25-8.10 (9
H, m).

(17b-2) N-3-methylcyclohexyl- [phenyl- (2-n-butylsulfonylphenyl) methyl] amine A mixture 315 of the intermediates (17a-2) and (17a-1)
mg, 2.5 ml trifluoroacetic acid and 0.5 ml
The reaction was carried out in the same manner as in Example (2b) using 30% aqueous hydrogen peroxide and purified, and only the portion of Rf = 0.48 (developing solvent: cyclohexane / ethyl acetate = 4/1) was taken. 62 mg of the title compound were obtained as colorless crystals. Melting point: 89-91 ° C. NMR spectrum (CDCl ₃ ) δ ppm: 0.75 (3H, t, J = 7.3H)
z), 0.83 (3H, d, J = 6.5Hz), 1.00-1.75 (12H, m), 1.88-2.0
0 (1H, m), 2.00-2.12 (1H, m), 2.30-2.45 (1H, m), 2.65-2.9
0 (2H, m), 6.30 (1H, s), 7.20-8.05 (9H, m).

Example 18 N-4-tert-butylcyclohexyl- [phenyl- (2-n-butylsulfonylphenyl) methyl] amine (Exemplary Compound No. 1-1443) (18a) N-4-tert-butylcyclohexyl-
[Phenyl- (2-n-butylthiophenyl) methyl]
Amine 600 mg of 2-n-butylthiobenzophenone and 0.
The reaction was carried out in the same manner as in Example (2a) using 79 ml of 4-tert-butylcyclohexylamine, and purification was performed to obtain 362 mg of the title compound as colorless crystals. Melting point: 81-83 ° C NMR spectrum (CDCl ₃ ) δppm: 0.80 (9H, s), 0.85-
1.15 (4H, m), 0.91 (3H, t, J = 7.3Hz), 1.30-1.80 (8H, m),
2.00-2.15 (2H, m), 2.22-2.40 (1H, m), 2.75-2.90 (2H, m),
5.63 (1H, s), 7.10-7.55 (9H, m).

(18b) N-4-tert-butylcyclohexyl- [phenyl- (2-n-butylsulfonylphenyl) methyl] amine N-4-tert-butylcyclohexyl- [phenyl- (2 -N-butylthiophenyl)
Methyl] amine 358 mg, 1.5 ml trifluoroacetic acid and 0.4 ml 30% hydrogen peroxide solution,
The reaction was carried out and purified in the same manner as in Example (2b), to give 272 mg of the title compound as colorless crystals. Melting point: 120-122 ° C NMR spectrum (CDCl ₃ ) δppm: 0.75 (3H, t, J = 7.3H)
z), 0.80 (9H, s), 0.85-1.80 (12H, m), 1.93-2.20 (2H, m),
2.30-2.45 (1H, m), 2.70-2.90 (2H, m), 6.30 (1H, s), 7.2
0-8.05 (9H, m).

Example 19 N-cyclohexyl- [p-tolyl- (2-cyclohexylcarbamoylphenyl) methyl] amine oxalate (Exemplified Compound No. 1-630) 500 mg of 2- (4-methylbenzoyl) benzoic acid and 0% The reaction was carried out in the same manner as in Example (2a) using 0.71 ml of cyclohexylamine, followed by purification to obtain 78.5 mg of the title compound as colorless crystals. Melting point: 183-185 ° C. NMR spectrum (d ₆ -DMSO) δ ppm: 0.95-2.20 (20H,
m), 2.27 (3H, s), 2.50-2.70 (1H, m), 6.01 (1H, s), 7.10-
7.65 (7h, m), 7.79 (1H, d, J = 7.7Hz), 8.52 (1H, d, J = 7.7Hz)
.

Example 20 N-((1R) -1-phenylethyl)-{phenyl-
[6-Fluoro-3- (1H-tetrazol-5-yl) phenyl] methyl} amine and its hydrochloride (Exemplary Compound No. 1-1876) (20a) N-((1R) -1-phenylethyl)-
[Phenyl- (3-cyano-6-fluorophenyl) methyl] amine 420 ml of 3-benzoyl-4-fluorobenzonitrile obtained in Reference Example 28 and 0.48 ml of (R) -1-
The reaction was carried out in the same manner as in Example (2a) using phenylethylamine, and the residue was purified. 230 mg of isomer A of the title compound was obtained as a yellow oil, and
03 mg was obtained. Isomer A NMR spectrum (CDCl ₃ ) δppm: 1.40 (3H, d, J = 6.7H
z), 3.61 (1H, q, J = 6.7Hz), 4.93 (1H, s), 7.06 (1H, dd, J =
(8.7Hz, J = 9.7Hz), 7.19-7.39 (10H, m), 7.53-7.58 (1H, m),
8.09 (1H, dd, J = 2.1 Hz, J = 6.7 Hz) Isomer B NMR spectrum (CDCl ₃ ) δ ppm: 1.39 (3H, d, J = 6.7H
z), 3.70 (1H, q, J = 6.7Hz), 4.97 (1H, s), 6.98 (1H, dd, J =
(8.6Hz, J = 9.7Hz), 7.19-7.39 (10H, m), 7.43-7.48 (1H, m),
7.89 (1H, dd, J = 2.1Hz, J = 6.7Hz).

(20b) N-((1R) -1-phenylethyl)-{phenyl- [6-fluoro-3- (1H-
Tetrazol-5-yl) phenyl] methyl} amine and its hydrochloride 225 mg of isomer A of Example (20a), 133 mg
And 158 ml of tri-butyltin chloride were reacted and purified in the same manner as in Example 1 to obtain 115 mg of a free form of isomer A of the title compound as a white powder. Isomer A Melting point: 122-125 ° C (decomposition) NMR spectrum (CDCl ₃ ) δppm: 1.55 (3H, d, J = 6.6H)
z), 3.99-4.06 (1H, m), 5.22 (1H, s), 7.09-7.41 (11H, m),
8.24-8.29 (1H, m), 8.79-8.81 (1H, m).

200 mg of isomer B of Example (20a), 118 mg of sodium azide and 0.52 ml
And purified by the same procedure as in Example 1 to obtain 210 mg of a free form of isomer B of the title compound as a white powder. This free body 20
The title compound was converted to the hydrochloride using 0 mg to give 98 mg as a yellow powder. Isomer B Melting point: 130-134 ° C NMR spectrum (CDCl ₃ ) δppm: 1.47 (3H, d, J = 6.6H)
z), 4.19-4.29 (1H, m), 5.36 (1H, s), 7.42-7.60 (11H, m),
8.05-8.09 (1H, m), 8.60-8.63 (1H, m), 10.1-11.0 (1H, b
rs).

Example 21 N-cyclohexyl- {phenyl- [4- (4-methylsulfonylphenyl) phenyl] methyl} amine oxalate (Exemplified Compound No. 1-215) (21a) N-cyclohexyl- {phenyl- [ 4-
(4-methylsulfonylphenyl) phenyl] methyl}
Amine The reaction was carried out in the same manner as in Example (2a) using 312 mg of 4- (4-methylthiophenyl) benzophenone obtained in Reference Example 8 and 0.23 ml of cyclohexylamine, and the title compound was purified by colorless crystals. 309mg as
Obtained. Melting point: 80-82 ° C NMR spectrum (CDCl ₃ ) δppm: 1.00-1.30 (5H, m),
1.45-2.05 (6H, m), 2.35-2.50 (1H, m), 2.51 (3H, s), 5.07
(1H, s), 7.15-7.55 (13H, m).

(21b) N-cyclohexyl- {phenyl- [4- (4-methylsulfonylphenyl) phenyl] methyl} amine oxalate N-cyclohexyl- {phenyl} of Example (21a)
The reaction was carried out in the same manner as in Example (2b) using 195 mg of [4- (4-methylsulfonylphenyl) phenyl] methyldiamine, 3.0 ml of trifluoroacetic acid and 0.5 ml of 30% hydrogen peroxide solution. Purification gave 20 mg of the title compound as colorless crystals. Melting point: 211-213 ° C. NMR spectrum (d ₆ -DMSO) δ ppm: 1.00-1.80 (8H, m),
2.05-2.20 (2H, m), 2.55-2.70 (1H, m), 3.26 (3H, s), 5.67
(1H, br.s), 7.30-8.05 (13H, m).

Example 22 N-trans-4-carboxycyclohexylmethyl-
[Phenyl- (2-ethylsulfonylphenyl) methyl] amine hydrochloride (Exemplary Compound No. 1-1174) N-trans-4-methoxycarbonylcyclohexylmethyl- [phenyl- (2-ethylsulfonylphenyl) obtained in Example 16 3.) Methyl] amine 0.30 g was dissolved in 6.0 ml of methanol, and stirred under ice-cooling.
Add 1 ml of 1N sodium hydroxide and add 6.5 ml at room temperature.
After stirring for an hour, the mixture was left overnight. Under ice-cooling and stirring, 2.1 ml of 1 N hydrochloric acid was added, the solvent was distilled off under reduced pressure, and benzene was added to the obtained residue, which was azeotropically dried. The obtained residue was dissolved in ethyl acetate and dried over anhydrous magnesium sulfate.
The solvent was distilled off under reduced pressure. The obtained residue was separated and purified by silica gel column chromatography using ethyl acetate as an eluent to give 75 mg of the title compound as colorless crystals. Melting point: 253-255 ° C (decomposition) NMR spectrum (d ₆ -DMSO) δ ppm: 0.80-1.35 (4H, m),
1.07 (3H, t, J = 7.3Hz), 1.70-1.98 (4H, m), 2.05-2.20 (1H,
m), 2.75 (2H, d, J = 3.3Hz), 3.21 (2H, q, J = 7.3Hz), 3.25-
3.50 (1H, m), 6.46 (1H, br.s), 7.30-7.50 (3H, m), 7.65-
7.80 (3H, m), 7.93 (1H, t, J = 7.6Hz), 8.01 (1H, d, J = 7.9H
z), 8.41 (1H, d, J = 7.8Hz), 10.00 (1H, br.s), 10.15 (1H, b
rs), 12.06 (1H, br.s).

Example 23 N- [trans-4- (N, N-dimethylcarbamoyl) cyclohexylmethyl]-[phenyl- (2-ethylsulfonylphenyl) methyl] amine (Exemplified Compound No. 1-1176) (23a) N -[Trans-4- (N, N-dimethylcarbamoyl) cyclohexylmethyl]-[phenyl-
(2-ethylthiophenyl) methyl] amine Using 0.50 g of 2-ethylthiobenzophenone obtained in Reference Example 6 and 0.91 g of trans-4- (N, N-dimethylcarbamoyl) cyclohexylmethylamine hydrochloride. Then, the reaction was carried out and purified in the same manner as in Example (2a) to obtain 0.67 g of the title compound as a pale yellow oil. NMR spectrum (CDCl ₃ ) δppm: 0.85-1.08 (2H, m),
1.30 (3H, t, J = 7.3Hz), 1.45-2.00 (8H, m), 2.35-2.50 (1H,
m), 2.46 (2H, d, J = 6.3Hz), 2.80-3.00 (2H, m), 2.94 (3H,
s), 3.03 (3H, s), 5.36 (1H, s), 7.10-7.55 (9H, m).

(23b) N- [trans-4- (N, N
-Dimethylcarbamoyl) cyclohexylmethyl]-
[Phenyl- (2-ethylsulfonylphenyl) methyl] amine N- [trans-4- (N, N-dimethylcarbamoyl) cyclohexylmethyl]-[phenyl- (2-ethylthiophenyl) methyl] of Example (23a) Amine 0.
60 g, 2.4 ml of trifluoroacetic acid and 0.83
The reaction was carried out in the same manner as in Example (2b) using 30 ml of 30% hydrogen peroxide solution and purified to obtain 0.36 g of the title compound as colorless columnar crystals. Melting point: 154-155 ° C NMR spectrum (CDCl ₃ ) δppm: 0.85-1.10 (2H, m),
1.15 (3H, t, J = 7.4Hz), 1.40-2.00 (8H, m), 2.30-2.60 (3H,
m), 2.85-3.10 (2H, m), 2.93 (3H, s), 3.02 (3H, s), 5.94
(1H, s), 7.20-7.50 (6H, m), 7.55-7.65 (1H, m), 7.77 (1H,
d, J = 7.7Hz), 8.03 (1H, dd, J = 1.2Hz, J = 7.9Hz).

Example 24 N-trans-4-hydroxymethylcyclohexylmethyl- [phenyl- (2-ethylsulfonylphenyl)
Methyl] amine hydrochloride (Exemplified Compound No. 1-1173) 0.50 g of N-trans-4-methoxycarbonylcyclohexylmethyl- [phenyl- (2-ethylsulfonylphenyl) methyl] amine obtained in Example 16 was added to 1
Dissolved in 0 ml of anhydrous tetrahydrofuran, and cooled with ice.
1.8 ml of a 1 mol solution of lithium aluminum hydride in anhydrous tetrahydrofuran was added, and the mixture was stirred at room temperature for 4 hours. Further, under ice-cooling and stirring, 1.0 ml of sodium sulfate decahydrate was added to the reaction solution, followed by stirring for 30 minutes. The insoluble material was removed by filtration using Celite, the filtrate was distilled off under reduced pressure, and the obtained residue was separated and purified by silica gel column chromatography (eluent: cyclohexane / ethyl acetate = 2 to 1/1) to give a colorless oil. 0.32 g was obtained. 2.0 g of this oil
It was dissolved in ml of dioxane, 2.0 ml of 4N hydrochloric acid / dioxane solution was added, and the solvent was distilled off under reduced pressure. The obtained residue was filtered using acetone and dried to obtain 0.22 g of the title compound as colorless crystals. Melting point: 182-184 ° C (decomposition) NMR spectrum (CDCl ₃ ) δppm: 0.75-1.10 (4H, m),
1.19 (3H, t, J = 7.3Hz), 1.30-1.98 (6H, m), 2.50-3.10 (4H,
m), 3.43 (2H, d, J = 6.2Hz), 6.70 (1H, br.s), 7.25-7.90 (7
H, m), 8.04 (1H, d, J = 6.0Hz), 8.46 (1H, d, J = 7.8Hz).

Example 25 N- (1-ethylpentyl)-{phenyl- [3- (1
H-tetrazol-5-yl) phenyl] methyl} amine hydrochloride (Exemplary Compound No. 1-447) N- (1-ethylpentyl)-{phenyl- [3- (1H-tetrazole-) obtained in Example 1 1.45 g of the free form of 5-yl) phenyl] methyl} amine in 100 m
After heating and dissolving in 1 l of ethyl acetate, 2.4 ml of 4N hydrochloric acid / ethyl acetate was added, and the mixture was concentrated under reduced pressure. The obtained residue was crystallized by adding isopropyl ether and collected by filtration to obtain 1.41 g of the title compound as pale yellow crystals. Melting point: 209-211 ° C. NMR spectrum (d ₆ -DMSO) δ ppm: 0.75-0.90 (6H, m),
1.10-1.37 (4H, m), 1.52-1.90 (4H, m), 2.80-2.90 (1H, m),
5.87 (1H, s), 7.30-8.20 (8H, m), 8.52 (1H, s).

Example 26 N-cyclohexyl- {phenyl- [2- (4-methylsulfonylphenyl) phenyl] methyl} amine (Exemplary Compound No. 1-125) (26a) N-cyclohexyl- {phenyl- [2-
(4-Methylthiophenyl) phenyl] methyl diamine Using 1.47 g of 2- (4-methylthiophenyl) benzophenone and 0.87 ml of cyclohexylamine, the reaction was carried out in the same manner as in Example (2a), followed by purification. 1.34 g of the title compound was obtained as a colorless oil. NMR spectrum (CDCl ₃ ) δ ppm: 0.85-1.20 (5H, m),
1.40-1.80 (6H, m), 2.18-2.30 (1H, m), 2.54 (3H, s), 5.14
(1H, s), 7.10-7.60 (13H, m).

(26b) N-cyclohexyl- {phenyl- [2- (4-methylsulfonylphenyl) phenyl] methyl} amine N-cyclohexyl- {phenyl} of Example (26a)
[2- (4-methylthiophenyl) phenyl] methyl}
The reaction was carried out in the same manner as in Example (2b) using 462 mg of the amine, 3.0 ml of trifluoroacetic acid and 0.5 ml of 30% aqueous hydrogen peroxide, followed by purification to obtain 379 mg of the title compound as colorless crystals. Melting point: 116-119 ° C NMR spectrum (CDCl ₃ ) δ ppm: 0.80-1.20 (5H, m),
1.40-1.80 (6H, m), 2.20-2.35 (1H, m), 3.12 (3H, s), 5.01
(1H, s), 7.05-8.05 (13H, m).

Example 27 N-cyclohexyl- [phenyl- (2-hydroxy-
4-methoxy-5-N, N-dimethylsulfamoylphenyl) methyl] amine oxalate (Exemplified Compound No. 1
-1602) 180 mg of 2-hydroxy-4 obtained in Reference Example 11
-Methoxy-5-N, N-dimethylsulfamoylbenzophenone, 0.135 ml of cyclohexylamine and a catalytic amount of p-toluenesulfonic acid monohydrate were refluxed and dehydrated in 30 ml of xylene for 20 hours. To the reaction solution were added 20 ml of anhydrous tetrahydrofuran and 0.27 ml of a 10 mol solution of borohydride-dimethyl sulfide complex at room temperature, and the mixture was stirred at room temperature for 30 minutes. The reaction solution was diluted with ethyl acetate, washed with saturated aqueous sodium hydrogen carbonate and saturated brine, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was separated and purified by silica gel column chromatography (elution solvent: cyclohexane / ethyl acetate = 5/1) to obtain colorless crystals. The crystals were dissolved in 5.0 ml of methanol and heated under reflux for 1 hour. The solvent was distilled off under reduced pressure, diluted with ethyl acetate, washed with saturated saline, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue is subjected to silica gel column chromatography (elution solvent: cyclohexane / ethyl acetate = 2 /
11. Separated and purified in 1), the title compound was converted into colorless crystals.
9 mg were obtained. Melting point: 168-170 ° C NMR spectrum (CDCl ₃ ) δppm: 1.00-1.80 (8H, m),
1.95-2.10 (2H, m), 2.55-2.70 (1H, m), 2.61 (6H, s), 5.60
(1H, s), 6.63 (1H, s), 7.30-7.55 (5H, m), 7.68 (1H, s).

Example 28 N-Cyclohexyl- [phenyl- (3-N-tosylcarbamoylphenyl) methyl] amine oxalate (Exemplary Compound No. 1-687) 948 mg of N-tosyl-3 obtained in Reference Example 13 Using -benzoylbenzoic acid amide and 0.57 ml of cyclohexylamine, the reaction was carried out in the same manner as in Example (2a), followed by purification to obtain 275 mg of the title compound as colorless crystals. Melting point: 225-227 ° C. NMR spectrum (d ₆ -DMSO) δ ppm: 0.90-1.75 (8H,
m), 2.05-2.20 (2H, m), 2.34 (3H, s), 2.65-2.75 (1H, m),
5.79 (1H, s), 7.24 (2H, d, J = 8.2Hz), 7.30-7.50 (4H, m),
7.60-7.70 (3H, m), 7.76 (2H, d, J = 8.3Hz), 7.87 (1H, d, J =
7.7Hz), 8.17 (1H, s).

Example 29 N-((1R) -1-phenylethyl)-[phenyl-
(2-ethylsulfonylphenyl) methyl] amine (Exemplified Compound No. 1-1181) (29a) N-((1R) -1-phenylethyl)-
[Phenyl- (2-ethylthiophenyl) methyl] amine Example using 1.0 g of 2-ethylthiobenzophenone obtained in Reference Example 6 and 1.1 ml of (R) -1-phenylethylamine The reaction was carried out in the same manner as in 2a) and purification was carried out to obtain 1.41 g of the title compound as a pale brown oil. NMR spectrum (CDCl ₃ ) δppm: 1.07 (2H, t, J = 7.3H
z), 1.18 (1H, t, J = 7.3Hz), 1.55-1.75 (4H, m), 2.50-2.83
(2H, m), 5.63 (0.35H, s), 5.68 (0.65H, s), 7.10-7.65 (13
H, m), 8.12 (1H, d, J = 7.5Hz).

(29b) N-((1R) -1-phenylethyl)-[phenyl- (2-ethylsulfonylphenyl) methyl] amine N-((1R) -1-phenylethyl) of Example (29a) Using [1.2 g of-[phenyl- (2-ethylthiophenyl) methyl] amine, 6.0 ml of trifluoroacetic acid and 1.6 ml of 30% hydrogen peroxide in water, Example (2)
Reaction and purification were carried out in the same manner as in b) to give 0.21 g of colorless needles of isomer A of the title compound (Rf = 0.25, cyclohexane 4: 1 ethyl acetate) as colorless crystals. Isomer B (Rf = 0.43, cyclohexane 4: 1
0.54 g of ethyl acetate) was obtained as a colorless oil, and the oil was converted into a hydrochloride to give 0.52 g of colorless crystals. Isomer A Melting point: 113-114 ° C. NMR spectrum (CDCl ₃ ) δ ppm: 0.91 (3H, t, J = 7.3H)
z), 1.47 (3H, d, J = 6.7Hz), 1.69 (1H, br.s), 2.20-2.40 (2
H, m), 3.76 (1H, q, J = 6.7Hz), 5.82 (1H, s), 7.20-7.67 (12
H, m), 7.80-8.00 (2H, m). Isomer B Melting point: 203-205 ° C (decomposition) NMR spectrum (d ₆ -DMSO) δppm: 0.84 (3H, t, J = 7.3H)
z), 1.72 (3H, d, J = 6.2Hz), 2.45-2.60 (2H, m), 4.20-4.40
(1H, br.s), 6.42 (1H, br.s), 7.25-8.05 (13H, m), 8.72 (1
H, d, J = 7.5Hz), 10.15-10.35 (1H, br.s), 11.10-11.35 (1
H, br.s).

Example 30 N-tert-butyl- [phenyl- (2-phenylsulfonylphenyl) methyl] amine hydrochloride (Exemplary Compound No. 1-1512) (30a) N-tert-butyl- [phenyl- (2-
Phenylthiophenyl) methyl] amine oxalate 500 mg of 2-phenylthiobenzophenone and 0.3 mg
Example 6 (2) using 6 ml of tert-butylamine
The reaction was carried out in the same manner as in a), followed by purification to obtain 220 mg of the title compound as colorless crystals. Melting point: 178-180 ° C (decomposition) NMR spectrum (d ₆ -DMSO) δppm: 1.16 (9H, s), 6.00
(1H, s), 7.20-7.65 (13H, m), 8.13 (1H, d, J = 7.9Hz).

(30b) N-tert-butyl- [phenyl- (2-phenylsulfonylphenyl) methyl] amine hydrochloride N-tert-butyl- [phenyl- (2-phenylthiophenyl) methyl of Example (30a) Amine oxalate 200 mg, 1.6 ml trifluoroacetic acid and 0.1 mg
Example (2b) using 3 ml of 30% hydrogen peroxide solution
And 110 mg of the title compound were obtained as colorless crystals. Melting point: 252-253 ° C (decomposition) NMR spectrum (d ₆ -DMSO) δppm: 1.23 (9H, s), 6.62
(1H, br.s), 7.20-8.05 (13H, m), 8.88 (1H, d, J = 8.0Hz),
9.64 (1H, br.s, J = 9.6Hz), 9.95-10.20 (1H, br.s).

Example 31 N-cyclohexyl- [phenyl- (2-methylsulfonyl-6-methoxyphenyl) methyl] amine oxalate (Exemplified Compound No. 1-910) (31a) N-cyclohexyl- [phenyl- (2- Methylthio-6-methoxyphenyl) methyl] amine oxalate 300 mg of 2-methylthio-6 obtained in Reference Example 14
Using methoxybenzophenone and 0.26 ml of cyclohexylamine, a reaction was carried out in the same manner as in Example (2a), and the purified imino form was obtained using 0.57 ml of a 10 mol solution of borohydride-dimethyl sulfide complex Then, the reaction was carried out in the same manner as in Example 27, followed by purification to obtain 26 mg of the title compound as colorless crystals. Melting point: 173-174 ° C (decomposition) NMR spectrum (d ₆ -DMSO) δppm: 0.90-2.10 (10H,
m), 2.50-2.70 (1H, m), 3.88 (3H, s), 5.82 (1H, s), 7.00-
7.60 (8H, m).

(31b) N-cyclohexyl- [phenyl- (2-methylsulfonyl-6-methoxyphenyl)
Methyl] amine oxalate N-cyclohexyl- [phenyl-] of Example (31a)
(2-Methylthio-6-methoxyphenyl) methyl] amine oxalate (26 mg), 1.0 ml of trifluoroacetic acid and 0.3 ml of 30% aqueous hydrogen peroxide were reacted in the same manner as in Example (2b). Purification gave 11.5 mg of the title compound as colorless crystals. Melting point: 92-95 ° C (decomposition) NMR spectrum (d ₆ -DMSO) δ ppm: 1.00-1.40 (5H, m),
1.45-2.15 (5H, m), 2.50-2.70 (1H, m), 3.09 (3H, s), 3.83
(3H, s), 6.40-6.80 (1H, br.s), 7.20-7.75 (8H, m).

Example 32 N- {4- (1-phenyl-1-[(N- (1R) -1]
-Phenylethyl) amino] methyl) phenyl {-N '
-P-toluenesulfonylurea (Exemplary Compound No. 1-
1791) (32a) N-((1R) -1-phenylethyl)-
{Phenyl- [4-N-acetylamino) phenyl] methyl} amine Using 1.08 mg of 4- (N-acetylamino) benzophenone and 1.15 ml of (R) -1-phenylethylamine, Example (2a) ), And purified to give 1.34 g of an isomer mixture of the title compound as a pale yellow foam. NMR spectrum (CDCl ₃ ) δ ppm: 1.35 (3H, d, J = 6.7H
z), 2.12 and 2.15 (total 3 H, each s), 3.65 (1H, q, J = 6.7H
z), 4.59 (1H, s), 7.11-7.64 (15H, m).

(32b) N-((1R) -1-phenylethyl)-[phenyl- (4-aminophenyl) methyl] amine N-((1R) -1-phenyl) obtained in Example (32a) To a solution of 1.33 g of ethyl)-{phenyl- [4-N-acetylamino) phenyl] methyl} amine in 20 ml of methanol was added 5 ml of concentrated hydrochloric acid, and the mixture was stirred at room temperature and heated under reflux for 1 hour. After cooling the reaction to room temperature,
100 ml of water was added and washed with methylene chloride. After the aqueous layer was neutralized with excess sodium bicarbonate, it was extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was separated and purified by silica gel column chromatography (elution solvent: cyclohexane / ethyl acetate = 5/1 to 1/1) to give the isomer A of the title compound as a colorless oil in 350 m
g, Isomer B, 380 mg as a colorless oil. Isomer A NMR spectrum (CDCl ₃ ) δ ppm: 1.35 (3H,
d, J = 6.7 Hz), 3.69 (1H, q, J =
6.7 Hz), 4.53 (1H, s), 6.65
(2H, d, J = 8.4 Hz), 7.09 (2H,
d, J = 8.4 Hz), 7.11-7.35 (10
H, m) Isomer B NMR spectrum (CDCl ₃ ) δ ppm: 1.35 (3H, d,
J = 6.7Hz), 3.65 (1H, q, J = 6.7Hz), 4.53 (1H, s), 6.56 (2H,
d, J = 8.5Hz), 7.04 (2H, d, J = 8.4Hz), 7.18-7.35 (10H, m).
(32c) N- {4- (1-phenyl-1-[(N-
(1R) -1-phenylethyl) amino] methyl) phenyl {-N'-p-toluenesulfonylurea 232 m
g of isomer A of Example (32b), 0.12 ml of p-
The reaction was carried out in the same manner as in Example (45a) using toluenesulfonyl isocyanate, followed by purification to obtain 25.5 mg of isomer A of the title compound as a yellow powder. Isomer A Melting point: 115-118 ° C (decomposition) NMR spectrum (d ₆ -DMSO) δppm: 1.29-1.40 (3H, br.
s), 2.37 (3H, s), 3.45-3.75 (1H, m), 4.35-4.80 (1H, m),
7.15-7.41 (16H, m), 7.80 (2H, d, J = 8.1Hz), 8.73 (1H, s) 264mg of isomer B of Example (32b), 0.13m
With 1 p-toluenesulfonyl isocyanate,
The reaction was conducted in the same manner as in Example (45a), and purification was performed to obtain 55.0 mg of isomer B of the title compound as a white powder. Isomer B Melting point: 101-102 ° C NMR spectrum (CDCl ₃ ) δ ppm: 1.38 (3H, d, J = 6.8H)
z), 2.41 (3H, s), 3.68 (1H, q, J = 6.7Hz), 4.60 (1H, s), 7.
20-7.36 (16H, m), 7.78 (2H, d, J = 8.4Hz), 8.38 (1H, br.s)
.

Example 33 N- {3- (1-phenyl-1-[(N- (1R) -1]
-Phenylethyl) amino] methyl) phenyl {-N '
-P-toluenesulfonylurea (Exemplary Compound No. 1-
1779) (33a) N-((1R) -1-phenylethyl)-
{Phenyl- [3-N-acetylamino) phenyl] methyl} amine Example (2a) using 2.0 g of 3- (N-acetylamino) benzophenone and 2.13 ml of (R) -1-phenylethylamine. ), Purify,
2.6 isomers of the title compound as pale yellow foams
4 g were obtained.

NMR spectrum (CDCl ₃ ) δ ppm: 1.34 and 1.35 (total 3H, d, J = 6.6 Hz respectively), 2.07 and 2.10 (total 3
H, each s), 3.61-3.71 (1H, m), 4.59 and 4.60 (total 1H,
S), 7.00-7.67 (15H, m), respectively.

(33b) N-((1R) -1-phenylethyl)-[phenyl- (3-aminophenyl) methyl] amine N-((1R) -1-phenyl) obtained in Example (32a) The reaction was carried out in the same manner as in Example (32b) using 2.64 g of ethyl)-{phenyl- [3-N-acetylamino) phenyl] methyl} amine, followed by purification to give isomer A of the title compound as a colorless oil. 287 mg, isomer B
Was obtained as a colorless oil. Isomer A NMR spectrum (CDCl ₃ ) δ ppm: 1.36 (3H, d, J = 6.7H
z), 3.72 (1H, q, J = 6.7Hz), 4.53 (1H, s), 6.56 (1H, d, J = 6.
8Hz), 6.67 (1H, s), 6.72 (1H, d, J = 7.8Hz), 7.10 (1H, dd, J
= 7.8Hz), 7.16-7.36 (10H, m) Isomer B NMR spectrum (CDCl ₃ ) δppm: 1.36 (3H, d, J = 6.7H)
z), 3.66 (1H, q, J = 6.7Hz), 4.53 (1H, s), 6.50 (1H, dd, J =
1.6Hz, J = 7.9Hz), 6.63-6.68 (2H, m), 7.03 (1H, dd, J = 7.7H
z, J = 7.8Hz), 7.23-7.36 (10H, m).

(33c) N- {3- (1-phenyl-1)
-[(N- (1R) -1-phenylethyl) amino] methyl) phenyl} -N'-p-toluenesulfonylurea 185 mg of isomer A of Example (33b), 0.10
The reaction was carried out in the same manner as in Example (45a) using 2 ml of p-toluenesulfonyl isocyanate and purified to obtain 70.0 mg of isomer A of the title compound as a white powder. Isomer A Melting point: 111-115 ° C. (softening) NMR spectrum (CDCl ₃ ) δ ppm: 1.40 (3H, d, J = 6.5H)
z), 2.35 (3H, s), 3.72-3.78 (1H, m), 4.58 (1H, s), 6.91-
7.52 (16H, m), 7.83 (2H, d, J = 8.2 Hz), 8.56 (1H, br.s) 220 mg of isomer B of Example (33b), 0.12 m
With 1 p-toluenesulfonyl isocyanate,
The reaction was conducted in the same manner as in Example (45a), and purification was performed to obtain 195 mg of isomer B of the title compound as a white powder. Isomer B Melting point: 107-111 ° C (softening) NMR spectrum (CDCl ₃ ) δppm: 1.40 (3H, d, J = 6.1H)
z), 2.38 (3H, s), 3.65-3.75 (1H, m), 4.59 (1H, s), 6.92-
7.48 (16H, m), 7.81 (2H, br.s), 8.56 (1H, br.s).

Example 34 N-Cyclohexyl- [phenyl- (2,4-dimethoxy-5-N, N-dimethylsulfamoylphenyl) methyl] amine oxalate (Exemplified Compound No. 1-187)
6) Using 410 mg of 2,4-dimethoxy-5-N, N-dimethylsulfamoylbenzophenone obtained in Reference Example 28 and 0.61 ml of cyclohexylamine, reacted in the same manner as in Example (2a). Imino form 4 obtained by purification
Example 2 was prepared using 5 mg and 0.0145 ml of a 10M borohydride-dimethylsulfide complex solution.
Reaction and purification were carried out in the same manner as in 7 to obtain 41.2 mg of a free form of the title compound as a yellow foam. Using this free form as an oxalate, the title compound was converted into 1 as a white powder.
8.2 mg were obtained. NMR spectrum (d ₆ -DMSO) δppm: 0.99-1.19 (3H, m),
1.20-1.40 (2H, m), 1.48-1.58 (1H, m), 1.65-1.78 (2H, m
m), 1.95-2.13 (2H, m), 2.50-2.70 (1H, m), 2.65 (6H, s),
3.93 (3H, s), 3.96 (3H, s), 5.71 (1H, br.s), 6.84 (1H, s),
7.29-7.58 (5H, m), 7.95 (1H, s). Example 35 N-cyclohexyl- [1-naphthyl- (2-methylsulfonylphenyl) methyl] amine (Exemplified Compound No. 2
-290) (35a) N-cyclohexyl- [1-naphthyl- (2
-Methylthiophenyl) methyl] amine oxalate Example (2a) using 2.34 g of 2-N-methylthiophenyl- (1-naphthyl) ketone obtained in Reference Example 15 and 1.92 ml of cyclohexylamine The reaction was carried out in the same manner as described above, followed by purification to obtain 2.73 g of the title compound as pale yellow crystals. Melting point: 189-191 ° C (decomposition) NMR spectrum (CDCl ₃ ) δppm: 1.00-1.30 (4H, m),
1.45-1.90 (5H, m), 2.10-2.30 (2H, m), 2.67 (3H, s), 3.05
-3.20 (1H, m), 6.74 (1H, s), 6.95-8.15 (11H, m). (35b) N-cyclohexyl- [1-naphthyl- (2
-Methylsulfonylphenyl) methyl] amine 2.73 g of N-cyclohexyl- [1-naphthyl- (2-methylthiophenyl) methyl] amine oxalate of Example (35a), 15 ml of trifluoroacetic acid and 3.0 ml of 30 Example (2)
The reaction was carried out in the same manner as in b) and purification was carried out to obtain 363 mg of the title compound as colorless crystals. Melting point: 139-141 ° C NMR spectrum (CDCl ₃ ) δppm: 1.00-1.80 (9H, m),
1.85-2.20 (2H, m), 2.55-2.70 (1H, m), 2.83 (3H, s), 7.16
(1H, d, J = 7.1Hz), 7.20-7.90 (8H, m), 8.15 (1H, dd, J = 1.2H
z, J = 7.9Hz), 8.34 (1H, d, J = 8.3Hz).

Example 36 N-((1R) -1-cyclohexylethyl)-{phenyl- [3- (1H-tetrazol-5-yl) phenyl] methyl} amine (Exemplified Compound No. 1-515) (36a) N-((1R) -1-cyclohexylethyl)-[phenyl- (3-cyanophenyl) methyl] amine 500 mg of 3-cyanobenzophenone and 0.71 ml
Using (R) -1-cyclohexylethylamine of
The reaction was carried out in the same manner as in Example (2a), and purification was carried out to obtain 557 mg of the title compound as a yellow oil. NMR spectrum (CDCl ₃ ) δ ppm: 0.94-1.26 (9H, m),
1.47-1.71 (5H, m), 2.28-2.44 (1H, m), 4.97 (1H, s), 7.22
-7.77 (9H, m).

(36b) N-((1R) -1-cyclohexylethyl)-{phenyl- [3- (1H-tetrazol-5-yl) phenyl] methyl} amine N-((1R) of Example (36a) ) -1) -Cyclohexylethyl)-[phenyl- (3-cyanophenyl) methyl] amine 550 mg, 337 mg of sodium azide and 1.40 ml of tri-n-butyltin chloride were reacted in the same manner as in Example 1. Purification gave 132 mg of the title compound as colorless crystals. Melting point: 216-218 ° C NMR spectrum (d ₆ -DMSO) δ ppm: 0.94-1.26 (8H, m),
1.47-1.71 (6H, m), 2.53-2.56 (1H, m), 5.39 (1H, m), 7.2
5-7.60 (7H, m), 7.89 (1H, d, J = 7.7Hz), 8.24 (1H, d, J = 6.0H
z).

Example 37 N- (1-ethylpentyl)-{phenyl- [4- (1
H-tetrazol-5-yl) phenyl] methyl} amine (Exemplified Compound No. 1-530) (37a) N- (1-ethylpentyl)-[phenyl-
(4-cyanophenyl) methyl] amine 1.0 g of 4-cyanobenzophenone and 1.46 g of 1
Example (2) using -ethylpentylamine hydrochloride
The reaction was carried out in the same manner as in a), followed by purification to obtain 1.44 g of the title compound as a pale yellow oil. NMR spectrum (CDCl ₃ ) δppm: 0.75-0.95 (6H, m),
1.15-1.55 (9H, m), 2.30-2.42 (1H, m), 4.98 (1H, s), 7.10
-7.60 (9H, m).

(37b) N- (1-ethylpentyl)-
｛Phenyl- [4- (1H-tetrazol-5-yl)
Phenyl] methyl} amine N- (1-ethylpentyl)-[phenyl- (4-cyanophenyl) methyl] amine of Example (37a) 1.1
6 g, 0.74 g sodium azide and 3.1 ml
The reaction was carried out in the same manner as in Example 1 by using tri-n-butyltin chloride, and purified to obtain 687 mg of the title compound as colorless crystals. Melting point: 219-221 ° C NMR spectrum (d ₆ -DMSO) δ ppm: 0.75-0.95 (6H, m),
1.10-1.60 (8H, m), 2.40-2.55 (1H, m), 5.26 (1H, s), 7.20
-7.45 (3H, m), 7.54 (2H, d, J = 7.7Hz), 7.66 (2H, d, J = 7.3H
z), 7.98 (2H, d, J = 8.2Hz).

Example 38 N- (1-Ethylpentyl)-[phenyl- (2-ethylsulfonylphenyl) methyl] amine hydrochloride (Exemplified Compound No. 1-1138) (38a) N- (1-ethylpentyl)- [Phenyl-
(2-ethylthiophenyl) methyl] amine oxalate Example (2a) using 0.50 g of 2-ethylthiobenzophenone obtained in Reference Example 6 and 0.63 g of 1-ethylpentylamine hydrochloride. 0.59 g of the obtained yellow oil was converted into oxalate as
0.47 g of the title compound was obtained as colorless crystals. Melting point: 131-133 ° C. NMR spectrum (CDCl ₃ ) δ ppm: 0.82-1.05 (6H, m),
1.20-1.45 (7H, m), 1.65-1.95 (4H, m), 2.85-3.05 (3H, m),
6.07 (1H, s), 7.20-7.70 (9H, m).

(38b) N- (1-ethylpentyl)-
[Phenyl- (2-ethylsulfonylphenyl) methyl] amine hydrochloride 0.45 g of N- (1-ethylpentyl)-[phenyl- (2-ethylthiophenyl) methyl] amine oxalate of Example (38a) The reaction was carried out in the same manner as in Example (2b) using 2.5 ml of trifluoroacetic acid and 0.6 ml of 30% aqueous hydrogen peroxide, followed by purification to obtain 0.35 g of the title compound as colorless crystals. Melting point: 176-178 ° C (decomposition) NMR spectrum (d ₆ -DMSO) δppm: 0.80-1.40 (13H,
m), 1.55-2.00 (4H, m), 3.05-3.30 (2H, m), 6.81 (1H, s),
7.20-7.50 (6H, m), 7.60-7.70 (1H, m), 7.93 (1H, d, J = 6.9H
z), 8.02 (1H, dd, J = 1.2Hz, J = 7.9Hz).

Example 39 N-cyclohexyl- {phenyl- [2- (2-methylsulfonylphenyl) phenyl] methyl} amine (Exemplified Compound No. 1-87) (39a) N-cyclohexyl- {phenyl- [2-
(2-methylsulfonylphenyl) phenyl] methyl}
Amine oxalate Using 0.99 g of 2- (2-methylthiophenyl) benzophenone obtained in Reference Example 17 and 0.76 ml of cyclohexylamine, reacted and purified in the same manner as in Example (2a). 925 mg of the title compound as colorless crystals
Obtained. NMR spectrum (CDCl ₃ ) δppm: 0.90-2.15 (11H, m),
2.40 (3H, s), 2.85-3.00 (1H, m), 5.11 (1H, s), 6.74 (1H,
d, J = 7.7Hz), 7.10-7.70 (11H, m), 8.08 (1H, d, J = 7.7Hz)
.

(39b) N-cyclohexyl- {phenyl- [2- (2-methylsulfonylphenyl) phenyl] methyl} amine N-cyclohexyl- {phenyl} of Example (39a)
[2- (2-methylthiophenyl) phenyl] methyl}
Using 925 mg of amine oxalate, 10 ml of trifluoroacetic acid and 3.0 ml of 30% hydrogen peroxide,
The reaction was carried out in the same manner as in Example (2b), and purification was carried out to obtain 70 mg of the title compound as pale pink crystals. Melting point: 137-138 ° C NMR spectrum (CDCl ₃ ) δppm: 0.80-1.25 (6H, m),
1.30-1.95 (5H, m), 2.15-2.30 (1H, m), 2.90 (3H, s), 4.87
(1H, s), 6.94 (1H, d, J = 7.5Hz), 7.03-7.75 (10H, m), 7.95
(1H, d, J = 7.8Hz), 8.31 (1H, d, J = 7.9Hz).

Example 40 N-cyclohexyl- {phenyl- [4- (2-methylsulfonylphenyl) phenyl] methyl} amine oxalate (Exemplified Compound No. 1-176) (40a) N-cyclohexyl- {phenyl- [ 4-
(2-Methylthiophenyl) phenyl] methyl} amine Using 0.93 g of 4- (2-methylthiophenyl) benzophenone obtained in Reference Example 18 and 0.71 ml of cyclohexylamine, as in Example (2a). React and purify to give the title compound as a pale yellow oil, 1.1.
4 g were obtained. NMR spectrum (CDCl ₃ ) δ ppm: 1.00-1.30 (6H, m),
1.50-1.75 (3H, m), 1.85-2.05 (2H, m), 2.35 (3H, s), 2.35-
2.50 (1H, m), 5.08 (1H, s), 7.10-7.50 (13H, m).

(40b) N-cyclohexyl- {phenyl- [4- (2-methylsulfonylphenyl) phenyl] methyl} amine oxalate N-cyclohexyl- {phenyl} of Example (40a)
[4- (2-methylthiophenyl) phenyl] methyl}
The reaction was carried out in the same manner as in Example (2b) using 1.12 g of amine, 5.0 ml of trifluoroacetic acid and 1.0 ml of 30% aqueous hydrogen peroxide, and purified to give the title compound as colorless crystals. 26 g were obtained. Melting point: 217-219 ° C NMR spectrum (d ₆ -DMSO) δppm: 1.05-2.30 (10H,
m), 2.65-2.80 (1H, m), 2.89 (3H, s), 5.76 (1H, s), 7.40-
7.90 (12H, m), 8.16 (1H, d, J = 7.6Hz).

Example 41 Nn-butyl- [phenyl- (2-butylsulfonylphenyl) methyl] amine oxalate (Exemplified Compound No. 1-1410) (41a) Nn-butyl- [phenyl- (2 -Butylthiophenyl) methyl] amine oxalate 500 mg of 2-n-butylthiobenzophenone and 0.1 mg
Example (2a) using 37 ml of n-butylamine
And purified to give a light brown oily substance
g was obtained. 533 mg of the obtained oil and 146 m of oxalic acid
Using g, 367 mg of the title compound was obtained as colorless crystals. Melting point: 151-153 ° C NMR spectrum (CDCl ₃ ) δppm: 0.79 (3H, t, J = 7.3H)
z), 0.88 (3H, t, J = 7.3Hz), 1.10-1.65 (8H, m), 2.72-2.96
(4H, m), 6.07 (1H, s), 7.15-7.60 (8H, m), 7.90-8.00 (1H,
m).

(41b) Nn-butyl- [phenyl-
(2-butylsulfonylphenyl) methyl] amine oxalate Nn-butyl- [phenyl- (2
-Butylthiophenyl) methyl] amine oxalate 36
0 mg was neutralized with aqueous sodium bicarbonate to obtain 281.2 mg of N-n.
-Butyl- [phenyl- (2-butylthiophenyl) methyl] amine, 2.0 ml of trifluoroacetic acid and 0.5
The reaction was carried out in the same manner as in Example (2b) using 30 ml of a 30% aqueous hydrogen peroxide solution, followed by purification to obtain 342 g of the title compound as colorless crystals. Melting point: 111-113 ° C. NMR spectrum (CDCl ₃ ) δ ppm: 0.77 (3H, t, J = 7.3H)
z), 0.81 (3H, t, J = 7.3Hz), 1.08-1.35 (4H, m), 1.35-1.70
(4H, m), 2.55-3.05 (4H, m), 6.59 (1H, s), 7.25-7.80 (7H,
m), 8.04 (1H, d, J = 7.9Hz), 8.16 (1H, d, J = 7.6Hz).

Example 42 N-((1R) -1-phenylethyl)-{phenyl-
[3- (1H-tetrazol-5-yl) phenyl] methyl} amine hydrochloride (Exemplary Compound No. 1-489) (42a) N-((1R) -1-phenylethyl)-
[Phenyl- (3-cyanophenyl) methyl] amine 621 mg of 3-cyanobenzophenone and 0.77 ml
(R) -1-phenylethylamine, and purified in the same manner as in Example (2a). Purification was performed using 293 mg of isomer A of the title compound as a pale yellow oil, and isomer B as a pale yellow oil. 328 mg were obtained. Isomer A NMR spectrum (CDCl ₃ ) δ ppm: 1.38 (3H,
d, J = 6.7 Hz), 3.59 (1H, q, J =
6.7 Hz, J = 13.3 Hz), 4.64 (1H,
s), 7.10-7.65 (13H, m), 7.7
2 (1H, s) isomer B NMR spectrum (CDCl ₃ ) δppm: 1.37 (3H,
d, J = 6.6Hz), 3.66 (1H, q, J = 6.6Hz, J = 13.2Hz), 4.61 (1H,
s), 7.15-7.55 (13H, m), 7.65 (1H, s).

(42b) N-((1R) -1-phenylethyl)-{phenyl- [3- (1H-tetrazole-
5-yl) phenyl] methyldiamine hydrochloride 293 mg of isomer A of Example (42a) and 183 mg
Of sodium azide and 0.81 ml of tri-n-butyltin chloride in the same manner as in Example 1 and purified to give isomer A of the title compound as colorless crystals.
mg. Isomer A Melting point: 247 ° -249 ° C. (decomposition) NMR spectrum (d ₆ -DMSO) δ ppm: 1.69 (3H, d, J = 6.7H)
z), 4.05-4.20 (1H, m), 5.46 (1H, s), 7.30-8.10 (13H, m),
8.34 (1H, s).

328 mg of isomer B of Example (42a)
And 204 mg of sodium azide and 0.90 ml of tri-n-butyltin chloride were reacted and purified in the same manner as in Example 1 to obtain 143 mg of isomer B of the title compound as colorless crystals. Isomer B Melting point: 174 ° C. (decomposition) NMR spectrum (d ₆ -DMSO) δ ppm: 1.70 (3H, d, J = 6.7H)
z), 4.10-4.25 (1H, m), 5.30 (1H, s), 7.30-8.10 (13H, m),
8.33 (1H, s).

Example 43 N-((1R) -1-phenylethyl)-{phenyl-
(3- [2- (2-methylphenyl) phenylsulfonylcarbamoyl] phenyl) methyl} amine hydrochloride (Exemplary Compound No. 1-802) (43a) N-((1R) -1-phenylethyl)-
{Phenyl- (3- [2- (2-methylphenyl) phenylsulfonylcarbamoyl] phenyl) methyl} amine N- [2- (2-methylphenyl) phenylsulfonyl] -3-benzoylbenzamide obtained in Reference Example 19 Reaction was carried out in the same manner as in Example (2a) using 250 mg and 0.14 ml of (R) -1-phenylethylamine,
Purification afforded isomer A of the title compound as a colorless oil
00 mg and 53 mg of isomer B were obtained as a colorless foam. Isomer A NMR spectrum (CDCl ₃ ) δ ppm: 1.37 (3H, d, J = 6.2H
z), 1.82 (1.2H, s), 1.85 (1.8H, s), 3.50-3.70 (1H, m),
4.63 (1H, s), 6.80-7.75 (22H, m), 8.42 (1H, d, J = 7.2Hz) Isomer B NMR spectrum (CDCl ₃ ) δppm: 1.37 (3H, d, J = 6.7H
z), 1.87 (1.4H, s), 1.90 (1.6H, s), 3.66 (1H, q, J = 6.7Hz,
J = 13.3Hz), 4.61 (1H, s), 6.85-7.70 (22H, m), 8.40 (1H,
d, J = 8.1Hz).

(43b) N-((1R) -1-phenylethyl)-{phenyl- (3- [2- (2-methylphenyl) phenylsulfonylcarbamoyl] phenyl) methyl} amine hydrochloride Example (43a) Was dissolved in 2.0 ml of ethyl acetate, and 0.045 ml of 4N hydrochloric acid /
A dioxane solution was added, and the mixture was concentrated under reduced pressure. The obtained residue was dissolved in 0.5 ml of ethyl acetate, and 10 ml of ether was further added thereto to give the title compound as pale yellow crystals in 51 m
g was obtained. 50 mg of isomer B of Example (43a)
Similarly, 30 mg of the title compound was obtained as pale yellow crystals from 22 ml of a 4 N hydrochloric acid / dioxane solution. Isomer A Melting point: 172-175 ° C. NMR spectrum (d ₆ -DMSO) δ ppm: 1.67 (3H, d, J = 6.5H
z), 1.85 (1.7H, s), 1.89 (1.3H, s), 4.00-4.20 (1H, m), 5.
36 (1H, s), 6.83-8.20 (22H, m), 9.90-10.15 (1H, m), 10.3
0-10.55 (1H, m), 12.14 (1H, br.s) Isomer B Melting point: 172-175 ° C. NMR spectrum (d ₆ -DMSO) δppm: 1.67 (3H, d, J = 6.6H)
z), 1.85 (1.5H, s), 1.86 (1.5H, s), 4.05-4.20 (1H, m), 5.
17 (1H, s), 6.85-8.20 (22H, m), 10.00-10.20 (1H, m), 10.
50-10.70 (1H, m), 12.11 (1H, br.s).

Example 44 N-((1R) -1-phenylethyl)-[phenyl-
(2-butylsulfonylphenyl) methyl] amine hydrochloride (Exemplary Compound No. 1-1456) (44a) N-((1R) -1-phenylethyl)-
[Phenyl- (2-butylthiophenyl) methyl] amine 668 mg of 2-n-butylthiobenzophenone and 0.1.
The reaction was carried out in the same manner as in Example (2a) using 63 ml of (R) -1-phenylethylamine and purified to obtain 919 mg of a pale brown oil. NMR spectrum (CDCl ₃ ) δppm: 0.87 (3H, m), 1.20-
1.55 (7H, m), 2.62-2.80 (2H, m), 3.60-3.80 (1H, m), 5.21
(0.5H, s), 5.36 (0.5H, s), 7.10-7.70 (14H, m).

(44b) N-((1R) -1-phenylethyl)-[phenyl- (2-butylsulfonylphenyl) methyl] amine hydrochloride 908 mg of N-((1R) -1 of Example (44a) −
Reaction was carried out in the same manner as in Example (2b) using phenylethyl)-[phenyl- (2-butylthiophenyl) methyl] amine, 1.5 ml of trifluoroacetic acid and 4.0 ml of 30% hydrogen peroxide. Purified, 402 mg of isomer A of the title compound as colorless crystals and 201 mg of isomer B
mg. Isomer A Melting point: 135 ° C. (decomposition) NMR spectrum (CDCl ₃ ) δ ppm: 0.57 (3H,
t, J = 7.2 Hz), 0.80-1.35 (7H,
m), 1.85-2.05 (2H, m), 3.90-
4.05 (1H, m), 6.43 (1H, br.
s), 7.10-8.00 (13H, m), 8.7
5-8.90 (1H, m) Isomer B Melting point: 209 ° C. (decomposition) NMR spectrum (CDCl ₃ ) δ ppm: 0.94 (3H, t,
J = 7.1Hz), 1.25-1.65 (4H, m), 1.73 (3H, d, J = 6.9Hz), 2.65
-2.98 (2H, m), 4.20-4.35 (1H, m), 6.32 (0.5H, s), 6.35
(0.5H, s), 7.30-7.95 (13H, m), 8.64 (1H, d, J = 8.1Hz).

Example 45 N- {2- [1-phenyl-1- (N- (1R) -1-]
Phenylethyl) amino] methyl} phenyl-N′-tosylurea oxalate (Exemplified Compound No. 1-1173)
9) (45a) N- (2-benzoylphenyl) -N'-tosylurea 500 mg of 2-aminobenzophenone and 0.385 m
1 ml of p-toluenesulfonyl isocyanate in 20 ml
Was dissolved in anhydrous benzene and refluxed for 4 hours. The reaction solution was diluted with 100 ml of ethyl acetate, and 10% aqueous hydrochloric acid was added.
The extract was washed with saturated saline, saturated aqueous sodium bicarbonate, and saturated saline, dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was separated and purified by silica gel column chromatography (elution solvent: cyclohexane / ethyl acetate = 3/1) to obtain 600 mg of the title compound as a pale yellow foam. NMR spectrum (CDCl ₃ ) δppm: 2.37 (3H, s), 7.05-
8.00 (14H, m).

(45b) N- ｛2- [1-phenyl-1
-(N- (1R) -1-phenylethyl) amino] methyl} phenyl-N'-tosylurea oxalate 600 mg of N- (2-benzoylphenyl) -N'-tosylurea of Example (45a) and 0 Example (2) using .39 ml of (R) -1-phenylethylamine
The reaction was carried out in the same manner as in a), followed by purification to obtain 85.9 mg of isomer A of the title compound as pale yellow crystals, and 24 mg of isomer B as oxalate salts as pale yellow crystals. Isomer A Melting point: 134-136 ° C NMR spectrum (d ₆ -DMSO) δppm: 1.46 (3H, d, J = 6.7
Hz), 2.44 (3H, s), 3.62 (1H, q, J = 6.7Hz, J = 13.5Hz), 4.70
(1H, s), 6.90-7.90 (18H, m) Isomer B Melting point: 127-129 ° C (decomposition) NMR spectrum (d ₆ -DMSO) δppm: 1.40 (3H, d, J = 2.7)
Hz), 2.39 (3H, s), 3.60-3.75 (1H, m), 4.76 (1H, s), 6.90
-7.90 (18H, m).

Example 46 N-((1R) -1-phenylethyl)-{2-benzothiazolyl- [3- (1H-tetrazol-5-yl)
Phenyl] methyl} amine (Exemplified Compound No. 3-47
0) (46a) N-((1R) -1-phenylethyl)-
[2-benzothiazolyl- (3-cyanophenyl) methyl] amine From 530 mg of (2-benzothiazolyl) -3-cyanophenyl ketone obtained in Reference Example 20 and 0.51 ml of (R) -1-phenylethylamine. , Example (2)
Reaction and purification were carried out as in a), giving 685 mg of the title compound as a yellow foam. NMR spectrum (CDCl ₃ ) δppm: 1.35-1.55 (3H, m),
3.71 (0.4H, q, J = 6.7Hz, J = 13.3Hz), 3.91 (0.6H, q, J = 6.7H
z, J = 13.3Hz), 5.05 (0.4H, s), 5.08 (0.6H, s), 7.10-8.10
(13H, m).

(46b) N-((1R) -1-phenylethyl)-{2-benzothiazolyl- [3- (1H-tetrazol-5-yl) phenyl] methyl} amine N- (of Example (46a) Example 1 was prepared using 384 mg of (1R) -1-phenylethyl)-[2-benzothiazolyl- (3-cyanophenyl) methyl] amine, 203 mg of sodium azide and 0.89 ml of tri-n-butyltin chloride. Reaction and purification were carried out in the same manner to obtain 63 mg of the title compound as colorless crystals. Melting point: 177-178 ° C (decomposition) NMR spectrum (d ₆ -DMSO) δppm: 1.30-1.50 (3H, m),
3.60-4.00 (1H, m), 5.00 (0.4H, s), 5.04 (0.6H, s), 7.20-
8.15 (14H, m).

Example 47 N-cyclohexyl- [phenyl- (2-n-propylsulfonylphenyl) methyl] amine (Exemplary Compound No. 1-1385) (47a) N-cyclohexyl- [phenyl- (2-n
-Propylthiophenyl) methyl] amine 0.5 g of 2-n-propylthiobenzophenone and 0.
Example 5 (2) using 5 ml of cyclohexylamine
The reaction was carried out in the same manner as in a), followed by purification to obtain 0.58 g of the title compound as a tan oil. NMR spectrum (CDCl ₃ ) δ ppm: 1.0 (3H, t, J = 7.3 Hz),
0.97-1.29 (5H, m), 1.43-1.71 (6H, m), 1.93-2.04 (2H,
m), 2.36-2.44 (1H, m), 2.85-2.90 (2H, m), 5.64 (1H, s),
7.13-7.55 (9H, m).

(47b) N-cyclohexyl- [phenyl- (2-n-propylsulfonylphenyl) methyl]
Amine N-cyclohexyl- [phenyl- of Example (47a)
(2-n-propylthiophenyl) methyl] amine
56 g, 2.4 ml of trifluoroacetic acid and 0.93
The reaction was carried out in the same manner as in Example (2b) using 30 ml of a 30% aqueous hydrogen peroxide solution and purified to obtain 0.25 g of the title compound as colorless crystals. Melting point: 62-64 ° C NMR spectrum (CDCl ₃ ) δppm: 0.74 (3H, t, J = 7.5H)
z), 0.98-1.69 (5H, m), 1.69-1.73 (6H, m), 1.73-2.06 (2
H, m), 2.37-2.46 (1H, m), 2.66 (2H, m), 6.29 (1H, s), 7.2
0-8.04 (9H, m).

Example 48 N-Cyclohexyl- {phenyl- [4- (1H-tetrazol-5-yl) phenyl] methyl} amine hydrochloride (Exemplary Compound No. 1-552) (48a) N-Cyclohexyl- [phenyl- (4-cyanophenyl) methyl] amine 361 mg of 4-cyanobenzophenone and 0.40 ml
The reaction was carried out in the same manner as in Example (2a) using cyclohexylamine, and purified to obtain 562 mg of the title compound as a pale yellow oil. NMR spectrum (CDCl ₃ ) δ ppm: 1.00-1.30 (5H, m),
1.40-2.00 (6H, m), 2.30-2.40 (1H, m), 5.07 (1H, s), 7.15
-7.65 (9H, m).

(48b) N-cyclohexyl- {phenyl- [4- (1H-tetrazol-5-yl) phenyl] methyl} amine hydrochloride N-cyclohexyl- [phenyl-
(4-cyanophenyl) methyl] amine 546 mg, 3
The reaction was carried out in the same manner as in Example 1 using 66 mg of sodium azide and 1.61 ml of tri-n-butyltin chloride, and the title compound was purified as colorless crystals.
9 mg were obtained. Melting point: 275-277 ° C (decomposition) NMR spectrum (d ₆ -DMSO) δppm: 1.00-1.80 (6H, m),
1.62-1.82 (2H, m), 2.14-2.30 (2H, m), 2.70-2.90 (1H,
m), 5.88 (1H, s), 7.30-7.60 (3H, m), 7.70-7.80 (2H, m),
7.90-8.03 (2H, m), 8.10-8.20 (2H, m), 9.72 (1H, br.s).

Example 49 N-Cyclohexyl- {phenyl- [3- (1H-tetrazol-5-yl) phenyl] methyl} amine hydrochloride (Exemplified Compound No. 1-469) (49a) N-cyclohexyl- [phenyl- (3-cyanophenyl) methyl] amine 414 mg of 3-cyanobenzophenone and 0.46 ml
The reaction was carried out in the same manner as in Example (2a) by using cyclohexylamine of the formula (1), and purified to obtain 531 mg of the title compound as a pale yellow oil. NMR spectrum (CDCl ₃ ) δ ppm: 1.00-2.00 (10H, m),
2.30-2.40 (1H, m), 5.10 (1H, s), 7.20-8.20 (9H, m).

(49b) N-cyclohexyl- {phenyl- [3- (1H-tetrazol-5-yl) phenyl] methyl} amine hydrochloride N-cyclohexyl- [phenyl-
(3-cyanophenyl) methyl] amine 531 mg, 3
The reaction was carried out in the same manner as in Example 1 using 55 mg of sodium azide and 1.56 ml of tri-n-butyltin chloride, and the title compound was obtained as colorless crystals by purification.
3 mg were obtained. Melting point: 272-273 ° C. (decomposition) NMR spectrum (d ₆ -DMSO) δ ppm: 1.00-1.20 (2H, m),
1.30-1.80 (6H, m), 2.15-2.40 (2H, m), 2.70-2.90 (1H,
m), 5.91 (1H, s), 7.30-7.90 (6H, m), 8.00-8.15 (2H, m),
8.45-8.50 (1H, m).

Example 50 N- (1-ethylpropyl)-{phenyl- [3- (1
H-tetrazol-5-yl) phenyl] methyl} amine hydrochloride (Exemplary Compound No. 1-513) (50a) N- (1-ethylpropyl)-[phenyl-
(3-cyanophenyl) methyl] amine 414 mg of 3-cyanobenzophenone and 0.24 ml
The reaction was carried out in the same manner as in Example (2a) using 3-aminopentane and purified to obtain 302 mg of the title compound as a pale yellow oil. NMR spectrum (CDCl ₃ ) δ ppm: 0.80-0.95 (6H, m),
1.35-1.60 (4H, m), 2.27-2.40 (1H, m), 4.96 (1H, s), 7.20
-7.80 (9H, m).

(50b) N- (1-ethylpropyl)-
@ Phenyl- [3- (1H-tetrazol-5-yl)
Phenyl] methyldiamine hydrochloride N- (1-ethylpropyl)-[phenyl- (3-cyanophenyl) methyl] amine 289 of Example (50a)
mg, 202 mg of sodium azide and 0.89 m
Example 1 using 1 l of tri-n-butyltin chloride
The reaction was carried out in the same manner as described above, and purification was performed to obtain 83 mg of the title compound as colorless crystals. Melting point: 229-232 ° C. (decomposition) NMR spectrum (d ₆ -DMSO) δ ppm: 0.75-0.95 (6H, m),
1.60-2.00 (4H, m), 2.70-2.90 (1H, m), 5.88 (1H, s), 7.
30-7.52 (3H, m), 7.60-7.90 (3H, m), 8.00-8.10 (2H, m),
8.50-8.55 (1H, m).

Example 51 N-((1R) -1-cyclohexylethyl)-{phenyl- [4- (1H-tetrazol-5-yl) phenyl] methyl} amine (Exemplified Compound No. 1-598) (51a) N-((1R) -1-cyclohexylethyl)-[phenyl- (4-cyanophenyl) methyl] amine 500 mg of 4-cyanobenzophenone and 0.71 ml
Using (R) -1-cyclohexylethylamine of
The reaction was carried out and purified in the same manner as in Example (2a) to give 182 mg of isomer A of the title compound as a pale yellow oil and 312 mg of isomer B as a pale yellow oil. Isomer A NMR spectrum (CDCl ₃ ) δ ppm: 0.94-1.36 (9H, m),
1.61-1.81 (5H, m), 2.27-2.36 (1H, m), 5.00 (1H, s), 7.25
-7.33 (5H, m), 7.54-7.61 (4H, m) isomer B NMR spectrum _{(CDCl 3) δppm: 0.91-1.40 (} 9H, m),
1.62-1.77 (5H, m), 2.35-2.44 (1H, m), 4.98 (1H, s), 7.19
-7.36 (5H, m), 7.52-7.59 (4H, m).

(51b) N-((1R) -1-cyclohexylethyl)-{phenyl- [4- (1H-tetrazol-5-yl) phenyl] methyl} amine hydrochloride 177 mg of the isomer of Example (51a) Body A, 109mg
And 0.46 ml of tri-n-butyltin chloride were reacted and purified in the same manner as in Example 1 to obtain 149 mg of the hydrochloride of isomer A of the title compound as colorless crystals. Isomer A Melting point: 243-245 ° C. (decomposition) NMR spectrum (d ₆ -DMSO) δ ppm: 0.91-1.36 (6H, m),
1.61-1.82 (4H, m), 1.91-2.02 (1H, m), 2.87-2.90 (1H,
m), 5.81 (1H, s), 7.35-7.48 (3H, m), 7.85 (2H, d, J = 7.2H
z), 8.03 (2H, d, J = 8.3Hz), 8.15 (2H, d, J = 8.3Hz), 9.37-
9.89 (2H, m).

306 mg of isomer B of Example (51a), 250 mg of sodium azide and 1.04 ml
The reaction was carried out in the same manner as in Example 1 by using tri-n-butyltin chloride, and purified to obtain 185 mg of isomer B of the title compound as colorless crystals. Isomer B Melting point: 235-238 ° C. NMR spectrum (d ₆ -DMSO) δ ppm: 0.89-1.38 (9H, m),
1.45-2.56 (6H, m), 5.27 (1H, s), 7.26-7.39 (3H, m), 7.
53 (2H, d, J = 7.2Hz), 7.66 (2H, d, J = 8.3Hz), 7.98 (2H, d, J =
8.3Hz).

Example 52 N-[(1R) -1- (4-bromophenyl) ethyl]
-{Phenyl- [4- (1H-tetrazol-5-yl) phenyl] methyl} amine (Exemplified Compound No. 1-6
00) (52a) N-[(1R) -1- (4-bromophenyl) ethyl]-[phenyl- (4-cyanophenyl) methyl] amine 518 mg of 4-cyanobenzophenone and 1 g of (R)
Using -1- (4-bromophenyl) ethylamine,
The reaction was carried out and purified in the same manner as in Example (2a) to give 347 mg of isomer A of the title compound as colorless crystals and 266 mg of isomer B as a pale yellow oil. Isomer A NMR spectrum (CDCl ₃ ) δ ppm: 1.35 (3H, d, J = 6.6H
z), 3.57 (1H, q, J = 6.6Hz), 4.62 (1H, s), 7.07 (2H, d, J = 8.
3Hz), 7.19-7.28 (5H, m), 7.46 (2H, d, J = 8.3Hz), 7.62 (2
H, d, J = 8.3 Hz) Isomer B NMR spectrum (CDCl ₃ ) δ ppm: 1.34 (3H, d, J = 6.6H)
z), 3.64 (1H, q, J = 6.6Hz), 4.59 (1H, s), 7.13 (2H, d, J = 8.
5Hz), 7.21-7.48 (9H, m), 7.53 (2H, d, J = 8.3Hz).

(52b) N-[(1R) -1- (4-bromophenyl) ethyl]-{phenyl- [4- (1H-
Tetrazol-5-yl) phenyl] methyl} amine 247 mg of isomer A of Example (52a), 123 mg
Of sodium azide and 0.51 ml of tri-n-butyltin chloride in the same manner as in Example 1, and purified to obtain 135 mg of isomer A of the title compound as colorless crystals. Isomer A Melting point: 231-233 ° C. NMR spectrum (d ₆ -DMSO) δ ppm: 1.31 (3H, d, J = 6.6H)
z), 3.56 (1H, q, J = 6.6Hz), 4.61 (1H, s), 7.16-7.37 (7H,
m), 7.50-7.60 (4H, m), 8.00 (2H, d, J = 8.3Hz).

261 mg of isomer B of Example (52a), 131 mg of sodium azide and 0.55 ml
The reaction was carried out and purified in the same manner as in Example 1 using tri-n-butyltin chloride, to obtain 43 mg of isomer B of the title compound as pale yellow crystals. Isomer B Melting point: 230-232 ° C. NMR spectrum (d ₆ -DMSO) δ ppm: 1.31 (3H, d, J = 6.6H)
z), 3.56 (1H, q, J = 6.6Hz), 4.61 (1H, s), 7.21-7.40 (7H,
m), 7.50-7.57 (4H, m), 7.92 (2H, d, J = 8.2Hz).

Example 53 N-((1S) -1-phenylethyl)-{phenyl-
[4- (1H-tetrazol-5-yl) phenyl] methyl} amine (Exemplary Compound No. 1-572) (53a) N-((1S) -1-phenylethyl)-
[(4-Cyanophenyl) phenylmethyl] amine Using 1 g of 4-cyanobenzophenone and 1.22 ml of (S) -1-phenylethylamine, reacted in the same manner as in Example (2a), purified, and 413 mg of isomer A of the compound was obtained as a pale yellow oil, and 155 mg of isomer B was obtained as a pale yellow oil. Isomer A NMR spectrum (CDCl ₃ ) δ ppm: 1.38 (3H, d, J = 6.7H
z), 3.60 (1H, q, J = 6.7Hz), 4.65 (1H, s), 7.14-7.38 (10H,
m), 7.49 (2H, d, J = 8.3 Hz), 7.61 (2H, d, J = 8.3 Hz) Isomer B NMR spectrum (CDCl ₃ ) δ ppm: 1.37 (3H, d, J = 6.6 H)
z), 3.67 (1H, q, J = 6.6Hz), 4.64 (1H, s), 7.21-7.38 (10H,
m), 7.41 (2H, d, J = 8.4Hz), 7.52 (2H, d, J = 8.4Hz). (53b) N-((1S) -1-phenylethyl)-
｛Phenyl- [4- (1H-tetrazol-5-yl)
Phenyl] methyldiamine 395 mg, isomer A of example (53a), 246 mg
Of sodium azide and 1.03 ml of tri-n-butyltin chloride in the same manner as in Example 1, and purified to obtain 383 mg of isomer A of the title compound as colorless crystals. Isomer A Melting point: 200-202 ° C. NMR spectrum (d ₆ -DMSO) δ ppm: 1.34 (3H, d, J = 6.6H)
z), 3.60 (1H, q, J = 6.6Hz), 4.67 (1H, s), 7.16-7.38 (10H,
m), 7.58 (2H, d, J = 8.2Hz), 7.99 (2H, d, J = 8.2Hz). Using 145 mg of isomer B of Example (53a), 91 mg of sodium azide and 0.38 ml of tri-n-butyltin chloride, the reaction was carried out in the same manner as in Example 1,
Purification afforded isomer B of the title compound as colorless crystals.
9 mg were obtained. Isomer B Melting point: 222-224 ° C. NMR spectrum (d ₆ -DMSO) δ ppm: 1.34 (3H, d, J = 6.7H)
z), 3.59 (1H, q, J = 6.7Hz), 4.65 (1H, s), 7.21-7.41 (10H,
m), 7.54 (2H, d, J = 8.3Hz), 7.93 (2H, d, J = 8.3Hz).

Example 54 N- (1-methylethyl)-{phenyl- [3- (1H
-Tetrazol-5-yl) phenyl] methyl} amine hydrochloride (Exemplary Compound No. 1-442) (54a) N- (1-methylethyl)-[phenyl-
(3-Cyanophenyl) methyl] amine Using 2.07 g of 3-cyanobenzophenone and 4.3 ml of isopropylamine, the reaction was carried out in the same manner as in Example (2a) and the compound was purified to give the title compound as a pale yellow oil 1.65 g was obtained. NMR spectrum (CDCl ₃ ) δ ppm: 1.00-1.16 (6H, m),
2.60-2.80 (1H, m), 4.98 (1H, s), 7.20-7.80 (9H, m).

(54b) N- (1-methylethyl)-
@ Phenyl- [3- (1H-tetrazol-5-yl)
Phenyl] methyl diamine hydrochloride N- (1-methylethyl)-[phenyl- (3-cyanophenyl) methyl] amine of Example (54a) 1.64
g, 1.28 g of sodium azide and 3.74 ml
The reaction was carried out in the same manner as in Example 1 by using tri-n-butyltin chloride, and purified to obtain 112 mg of the title compound as colorless crystals. Melting point: 273-275 ° C (decomposition) NMR spectrum (d ₆ -DMSO) δ ppm: 1.20-1.30 (6H, m),
3.00-3.20 (1H, m), 5.87 (1H, s), 7.35-7.50 (3H, m), 7.6
5-7.85 (3H, m), 7.95-8.10 (2H, m), 8.45-8.50 (1H, m).

Example 55 Nt-butyl- {phenyl- [3- (1H-tetrazol-5-yl) phenyl] methyl} amine hydrochloride (Exemplary Compound No. 1-444) (55a) Nt-butyl -[Phenyl- (3-cyanophenyl) methyl] amine 414 mg of 3-cyanobenzophenone and 1.05 ml
The reaction was carried out in the same manner as in Example (2a) using t-butylamine, and purified to obtain 132 mg of the title compound as a pale yellow oil. NMR spectrum (CDCl ₃ ) δ ppm: 1.05 (9H, s), 5.02 (1
H, s), 7.15-7.50 (7H, m), 7.63-7.72 (1H, m), 7.84-7.90
(1H, m).

(55b) Nt-butyl-diphenyl-
[3- (1H-tetrazol-5-yl) phenyl] methyl} amine hydrochloride Nt-butyl- [phenyl- (3
-Cyanophenyl) methyl] amine 119 mg, 176
mg sodium azide and 0.52 ml tri-n
Using -butyltin chloride, the reaction was carried out and purified in the same manner as in Example 1, whereby the title compound was obtained as colorless crystals in an amount of 92 mg.
Obtained. Melting point: 262-264 ° C (decomposition) NMR spectrum (d ₆ -DMSO) δppm: 1.29 (9H, s), 5.89
(1H, s), 7.30-7.50 (3H, m), 7.60-7.72 (1H, m), 7.85-8.0
6 (3H, m), 8.10-8.22 (1H, m), 8.54-8.63 (1H, m).

Example 56 N-((1S) -1-phenylethyl)-{phenyl-
[3- (1H-tetrazol-5-yl) phenyl] methyl} amine hydrochloride (Exemplary Compound No. 1-489) (56a) N-((1S) -1-phenylethyl)-
[Phenyl- (3-cyanophenyl) methyl] amine 621 mg of 3-cyanobenzophenone and 0.77 ml
(S) -1-phenylethylamine, and purified in the same manner as in Example (2a). Purification was performed to obtain 331 mg of isomer A of the title compound as a pale yellow oil, and 333 mg of isomer B as colorless crystals. I got Isomer A NMR spectrum (CDCl ₃ ) δ ppm: 1.38 (3H, d, J = 6.7H
z), 3.59 (1H, q, J = 6.7Hz), 4.64 (1H, s), 7.10-7.65 (13H,
m), 7.72 (1H, s) Isomer B NMR spectrum (CDCl ₃ ) δ ppm: 1.37 (3H, d, J = 6.6H)
z), 3.66 (1H, q, J = 6.6Hz), 4.61 (1H, s), 7.15-7.55 (13H,
m), 7.65 (1H, s).

(56b) N-((1S) -1-phenylethyl)-{phenyl- [3- (1H-tetrazole-
5-yl) phenyl] methyldiamine hydrochloride 321 mg of isomer A of example (56a), 200 mg
And 0.88 ml of tri-n-butyltin chloride were reacted and purified in the same manner as in Example 1 to obtain 147 mg of the hydrochloride of isomer A of the title compound as colorless crystals. Isomer A Melting point: 241-244 ° C. (decomposition) NMR spectrum (d ₆ -DMSO) δ ppm: 1.69 (3H, d, J = 6.7H)
z), 4.05-4.20 (1H, m), 5.46 (1H, s), 7.30-8.10 (13H, m),
8.34 (1H, s).

312 mg of isomer B of Example (56a), 195 mg of sodium azide and 0.86 ml
The reaction was carried out in the same manner as in Example 1 by using tri-n-butyltin chloride, and purified to obtain 179 mg of isomer B of the title compound as colorless crystals. Isomer B Melting point: 168 ° C (decomposition) NMR spectrum (d ₆ -DMSO) δppm: 1.70 (3H, d, J = 6.7H)
z), 4.10-4.25 (1H, m), 5.30 (1H, m), 7.30-8.10 (13H, m),
8.33 (1H, m).

Example 57 N-((1R) -1-phenylethyl)-{phenyl-
[4- (1H-tetrazol-5-yl) phenyl] methyl} amine (Exemplary Compound No. 1-572) (57a) N-((1R) -1-phenylethyl)-
[Phenyl- (4-cyanophenyl) methyl] amine Using 1 g of 4-cyanobenzophenone and 1.22 ml of (R) -1-phenylethylamine, the reaction was carried out in the same manner as in Example (2a), followed by purification. 197 mg of isomer A of the title compound was obtained as a pale yellow oil, and 165 mg of isomer B was obtained as a pale yellow oil. Isomer A NMR spectrum (CDCl ₃ ) δ ppm: 1.38 (3H,
d, J = 6.7 Hz), 3.59 (1H, q, J =
6.7 Hz), 4.65 (1H, s), 7.17-
7.38 (10H, m), 7.49 (2H, d, J =
8.2 Hz), 7.61 (2H, d, J = 8.2H)
z) Isomer B NMR spectrum (CDCl ₃ ) δ ppm: 1.37 (3H, d,
J = 6.6Hz), 3.67 (1H, q, J = 6.6Hz), 4.64 (1H, s), 7.23-7.3
8 (10H, m), 7.41 (2H, d, J = 8.2Hz), 7.52 (2H, d, J = 8.2Hz). (57b) N-((1R) -1-phenylethyl)-
｛Phenyl- [4- (1H-tetrazol-5-yl)
Phenyl] methyldiamine 193 mg of isomer A of Example (57a), 120 mg
Of sodium azide and 0.5 ml of tri-n-butyltin chloride in the same manner as in Example 1.
Purification gave 185 mg of the hydrochloride salt of isomer A of the title compound as colorless crystals. Isomer A Melting point: 222-229 ° C (decomposition) NMR spectrum (CDCl ₃ ) δppm: 1.86 (3H, d, J = 6.7H)
z), 4.12 (1H, m), 4.77 (1H, s), 7.13 (3H, m), 7.34-7.52
(7H, m), 7.92 (2H, d, J = 8.2Hz), 8.44 (2H, d, J = 8.2Hz), 1
0.20-10.43 (1H, m), 11.13-11.36 (1H, m).

The same reaction as in Example 1 was carried out using 160 mg of isomer B of Example (57a), 99 mg of sodium azide and 0.42 ml of tri-n-butyltin chloride, and the title compound was purified. 18 mg of isomer B was obtained as colorless crystals. Isomer B Melting point: 226 ° C.-228 ° C. (decomposition) NMR spectrum (d ₆ -DMSO) δ ppm: 1.34 (3H, d, J = 6.6H)
z), 3.59 (1H, q, J = 6.6Hz), 4.65 (1H, s), 7.23-7.40 (10H,
m), 7.54 (2H, d, J = 8.2Hz), 7.93 (2H, d, J = 8.2Hz).

Example 58 N-((1R) -1-naphthylethyl)-{phenyl-
[4- (1H-tetrazol-5-yl) phenyl] methyl} amine (Exemplary Compound No. 1-606) (58a) N-((1R) -1-naphthylethyl)-
[Phenyl- (4-cyanophenyl) methyl] amine 500 mg of 4-cyanobenzophenone and 0.77 ml
(R) -1-naphthylethylamine in the same manner as in Example (2a), and purified to obtain 885 mg of the title compound as a pale yellow oil. NMR spectrum (CDCl ₃ ) δ ppm: 1.49-1.54 (3H, m),
4.47-4.58 (1H, m), 4.72 and 4.75 (1H in total, S each), 7.1
8-7.67 (13H, m), 7.77-7.94 (3H, m).

(58b) N-((1R) -1-naphthylethyl)-{phenyl- [4- (1H-tetrazole-
5-yl) phenyl] methyl} amine 880 mg of N-((1R) -1-naphthylethyl)-[phenyl- (4-cyanophenyl) methyl] amine of Example (58a), 468 mg of sodium azide and 1.95 ml The reaction was carried out in the same manner as in Example 1 using tri-n-butyltin chloride, and purified to obtain 177 mg of the title compound as colorless crystals. Melting point: 204-206 ° C (decomposition) NMR spectrum (d ₆ -DMSO) δppm: 1.47 (3H, d, J = 6.5H)
z), 4.49 (1H, q, J = 6.5Hz), 4.79 (1H, s), 7.24-7.62 (10H,
m), 7.78-7.84 (3H, m), 7.91-7.96 (3H, m).

Example 59 N-((1R) -1-phenylethyl)-[phenyl-
(3-Mesylcarbamoylphenyl) methyl] amine hydrochloride (Exemplary Compound No. 1-640) Performed using 248 mg of N-mesyl-3-benzoylbenzoic acid amide and 0.21 ml of (R) -1-phenylethylamine. The reaction was performed and purified in the same manner as in Example (2a) to give 190 mg of the title compound as colorless crystals. Melting point: 148-152 ° C NMR spectrum (d ₆ -DMSO) δ ppm: 1.65-1.75 (3H, m),
3.35 (3H, s), 4.10 (1H, S), 5.20 and 5.35 (total 1H, each s), 7.30-8.20 (14H, m).

Example 60 N-((1R) -1-phenylethyl)-[phenyl-
(3-Tosylcarbamoylphenyl) methyl] amine hydrochloride (Exemplified Compound No. 1-696) This was carried out using 478 mg of N-tosyl-3-benzoylbenzoic acid amide and 0.32 ml of (R) -1-phenylethylamine. The reaction was carried out and purified in the same manner as in Example (2a), and 189 mg of the free isomer A of the title compound as a pale yellow oily substance and 218 mg of isomer B as a pale yellow oily substance were obtained.
mg was obtained. Using 117 mg of isomer A, 99 mg of the title compound was obtained as the hydrochloride salt. Similarly, 132 mg of isomer B was used to obtain 115 mg of the title compound as the hydrochloride salt. Isomer A Melting point: 147-149 ° C. NMR spectrum (d ₆ -DMSO) δ ppm: 1.69 (3H, d, J = 6.7H)
z), 2.40 (3H, s), 4.00-4.15 (1H, m), 5.33 (1H, s), 7.25-
8.10 (18H, m) Isomer B Melting point: 144-146 ° C NMR spectrum (d ₆ -DMSO) δppm: 1.68 (3H, d, J = 6.7H
z), 2.40 (3H, s), 4.00-4.20 (1H, m), 5.20 (1H, s), 7.22-
8.10 (18H, m).

Example 61 N-((1R) -indan-1-yl)-{phenyl-
[4- (1H-tetrazol-5-yl) phenyl] methyl} amine (Exemplary Compound No. 1-568) (61a) N-((1R) -indan-1-yl)-
[Phenyl- (4-cyanophenyl) methyl] amine 300 mg of 4-cyanobenzophenone and 0.37 ml
(R) -1-aminoindan of Example (2)
The reaction was carried out in the same manner as in a) and purification was carried out to obtain 478 mg of the title compound as a pale yellow oil. NMR spectrum (CDCl ₃ ) δ ppm: 1.72-1.88 (1H, m),
2.35-2.53 (1H, m), 2.69-2.81 (1H, m), 2.90-3.13 (1H, m),
4.12 (1H, q, J = 6.7Hz), 5.15 (1H, s), 7.19-7.71 (13H,
m).

(61b) N-((1R) -indane-1
-Yl)-{phenyl- [4- (1H-tetrazole-
5-yl) phenyl] methyl} amine N-((1R) -indan-1-yl)-[phenyl- (4-cyanophenyl) methyl] amine of Example (61a) 470 mg, 283 mg of sodium azide and The reaction was carried out in the same manner as in Example 1 using 18 ml of tri-n-butyltin chloride and purified to obtain 309 mg of the title compound as colorless crystals. Melting point: 212 ° C. NMR spectrum (d ₆ -DMSO) δ ppm: 1.83-2.01 (1H, m),
2.23-2.36 (1H, m), 2.62-2.74 (1H, m), 2.90-3.01 (1H, m
m), 4.05-4.10 (1H, m), 5.27 (1H, s), 7.19-7.39 (6H, m),
7.51-7.64 (3H, m), 7.73-7.82 (2H, m), 7.96-8.04 (2H, m)
.

Example 62 N- (4-carbamoylphenylmethyl)-{phenyl- [3- (1H-tetrazol-5-yl) phenyl]
Methyl diamine (Exemplified Compound No. 1-521) (62a) N- (4-methoxycarbonylphenylmethyl)-[phenyl- (3-cyanophenyl) methyl] amine 1 g of 3-cyanobenzophenone and 1.94 g of 4- Using aminomethylbenzoic acid methyl ester hydrochloride,
The reaction was conducted in the same manner as in Example (2a), and purification was performed to obtain 1.81 g of the title compound as a yellow oil. NMR spectrum (CDCl ₃ ) δ ppm: 3.79 (2H, s), 3.92 (3
H, s), 4.85 (1H, s), 7.17-7.72 (10H, m), 7.77 (1H, s), 7.
99-8.02 (2H, m).

(62b) N- (4-carbamoylphenylmethyl)-[phenyl- (3-cyanophenyl) methyl] amine N- (4-methoxycarbonylphenylmethyl)-[phenyl- (3 -Cyanophenyl) methyl] amine in 300 ml of 1.5 ml of dimethylformamide, 0.1 ml of formamide and 0.1 mg of
After adding 2 ml of a 28% sodium methoxy / methanol solution at room temperature, the mixture was heated and stirred for 8 hours. 20 in the reaction solution
After adding 2 ml of aqueous sodium hydrogen carbonate and extracting twice with ethyl acetate, the organic layer was washed with saturated saline and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue is subjected to silica gel chromatography (elution solvent: cyclohexane /
Separation and purification with ethyl acetate = 1/2) gave 216 mg of the title compound as a pale yellow foam. NMR spectrum (CDCl ₃ ) δ ppm: 3.79 (2H, s), 4.85 (1
H, s), 5.60-6.16 (2H, m), 7.29-7.43 (8H, m), 7.52 (1H, d,
J = 7.8Hz), 7.66 (1H, d, J = 7.8Hz), 7.79 (3H, d, J = 8.3Hz).

(62c) N- (4-carbamoylphenylmethyl)-{phenyl- [3- (1H-tetrazol-5-yl) phenyl] methyl} amine N- (4-carbamoylphenylmethyl) of Example (62b) )-[Phenyl- (3-cyanophenyl) methyl]
The reaction was carried out in the same manner as in Example 1 using 210 mg of amine, 120 mg of sodium azide and 0.50 ml of tri-n-butyltin chloride, followed by purification to obtain 34 mg of the title compound as yellow crystals. Melting point: 144-154 ° C. NMR spectrum (d ₆ -DMSO) δ ppm: 3.73 (2H, s), 4.96
(1H, s), 7.18-7.62 (8H, m), 7.82-7.91 (4H, m), 8.17 (1H,
s).

Reference Example 1 2-methylthiobenzoic acid-2-pyridyl ester 5.54 g of 2-methylthiobenzoyl chloride and 1.4
1 g of 2-hydroxypyridine was heated to reflux in 12 ml of pyridine for 3 hours. Under reduced pressure, pyridine is distilled off,
The obtained residue was separated and purified by silica gel chromatography (elution solvent: cyclohexane / ethyl acetate = 1/1) to obtain 1.92 g of the title compound as a pale yellow oil. NMR spectrum (CDCl ₃ ) δppm: 2.47 (3H, s), 7.20-
8.50 (8H, m).

Reference Example 2 (2-Thienyl) -2-methylthiophenyl ketone 680 mg of 2-methylthiobenzoic acid-2-pyridyl ester obtained in Reference Example 1 and 0.23 ml of thiophene were added to 5.
The mixture was refluxed for 2 hours and 40 minutes in 0 ml of trifluoroacetic acid. The reaction solution was poured into aqueous sodium bicarbonate, neutralized, extracted with ethyl acetate, dried over anhydrous magnesium sulfate, and the solvent was distilled off. The obtained residue is subjected to silica gel chromatography.
(Eluent: cyclohexane / dichloromethane = 2 /
The compound was separated and purified in 1) to give the title compound as a pale brown oil.
34 mg were obtained. NMR spectrum (CDCl ₃ ) δppm: 2.44 (3H, s), 7.10-
7.60 (6H, m), 7.73 (1H, d, J = 4.6Hz).

Reference Example 3 3-methoxycarbonylbenzoic acid-2-pyridyl ester 5.96 g of 3-methoxycarbonylbenzoyl chloride and 1.43 g of 2-hydroxypyridine were added in 12.1 ml.
In pyridine for 3 hours. Pyridine was distilled off under reduced pressure, and the obtained residue was subjected to silica gel chromatography (elution solvent: cyclohexane / ethyl acetate = 2/1).
And purified the title compound as a pale yellow oil (2.6).
8 g were obtained. NMR spectrum (CDCl ₃ ) δppm: 3.87 (3H, s), 7.20-
8.50 (7H, m), 8.79 (1H, s).

Reference Example 4 (2-thienyl) -3-methoxycarbonylphenylketone 3-methoxycarbonylbenzoic acid-2- obtained in Reference Example 3
1.02 g of the pyridyl ester and 0.32 ml of thiophene were heated under reflux in 5.0 ml of trifluoroacetic acid for 4 hours. The reaction solution was poured into aqueous sodium bicarbonate, neutralized, extracted with ethyl acetate, dried over anhydrous magnesium sulfate, and the solvent was distilled off. The obtained residue is subjected to silica gel column chromatography (elution solvent: cyclohexane / dichloromethane =
The product was separated and purified by 1/2) to obtain 530 mg of the title compound as pale brown crystals. Melting point: 93-95 ° C NMR spectrum (CDCl ₃ ) δppm: 3.87 (3H, s), 7.15-
7.80 (4H, m), 8.01 (1H, d, J = 7.8Hz), 8.22 (1H, d, J = 7.9H
z), 8.48 (1H, s).

Reference Example 5 (Benzothiophen-3-yl)-(2-methylthiophenyl) ketone 556 mg of 2-methylthiobenzoic acid-2-pyridyl ester obtained in Reference Example 1 and 456 mg of benzothiophene were added to 5.0 ml of triethylamine. The mixture was refluxed for 3.5 hours in fluoroacetic acid. The reaction solution was poured into aqueous sodium bicarbonate, neutralized, extracted with ethyl acetate, dried over anhydrous magnesium sulfate, and the solvent was distilled off. The obtained residue is subjected to silica gel column chromatography (elution solvent: cyclohexane / dichloromethane =
4/1) to give 397 mg of the title compound as a yellow oil. NMR spectrum (CDCl ₃ ) δppm: 2.44 (3H, s), 7.20-
7.95 (8H, m), 8.73 (1H, d, J = 7.6Hz).

Reference Example 6 2-ethylthiobenzophenone 11.0 g of 2-ethylthiobenzoyl chloride and 7.3 g
Was suspended in 120 ml of anhydrous benzene and stirred at room temperature for 18 hours. Pour the reaction into ice water,
Extracted with ethyl acetate. The extract was washed with an aqueous solution of sodium bicarbonate and saturated saline, dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was separated and purified by silica gel column chromatography (eluent: cyclohexane / ethyl acetate = 19/1) to give 8.73 g of the title compound as a yellow oil. NMR spectrum (CDCl ₃ ) δppm: 1.24 (3H, t, J = 7.4H
z), 2.88 (2H, q, J = 7.4Hz), 7.20-7.65 (7H, m), 7.79 (2H,
d, J = 7.2Hz).

Reference Example 7 N, N-dimethyl-2- (4-methylbenzoyl) benzamide 20 mg of 500 mg of 4-methylbenzoylbenzoic acid
Dissolved in anhydrous tetrahydrofuran and stirred under ice-cooling.
0.73 ml of triethylamine and 0.3 ml of isobutyl chloroformate were added and stirred for 1 hour. 204 in the reaction solution
mg of dimethylamine hydrochloride was added, and the mixture was stirred at room temperature for 2 hours. The mixture was diluted with ethyl acetate, washed with saturated aqueous sodium hydrogen carbonate and saturated brine, dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was separated and purified by silica gel column chromatography (elution solvent: cyclohexane / ethyl acetate = 10/1 to 2/1) to give 170 mg of the title compound as a colorless oil. NMR spectrum (CDCl ₃ ) δ ppm: 2.42 (3H, s), 2.90 (3
H, s), 2.94 (3H, s), 7.25 (2H, d, J = 7.9Hz), 7.35-7.60 (4H,
m), 7.71 (2H, d, J = 8.2Hz).

Reference Example 8 4-methylthiophenyl-4-benzophenone 757 mg of 4-bromobenzophenone was dissolved in 7.0 ml of toluene and 7.0 ml of ethanol, and 660 mg of 4-methylthiophenylboric acid, 7
5 mg of 20% palladium hydroxide-carbon and 7.0 m
l of saturated aqueous sodium bicarbonate was added, and the mixture was heated and refluxed for 9 hours under a nitrogen stream. The reaction solution was filtered using celite, diluted with ethyl acetate, washed with aqueous potassium hydrogen sulfate and saturated saline, and then
After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. The obtained residue is subjected to silica gel column chromatography (elution solvent: cyclohexane / dichloromethane = 4).
/ 1) to separate and purify the title compound as colorless crystals,
312 mg were obtained. Melting point: 162-164 ° C NMR spectrum (CDCl ₃ ) δ ppm: 2.54 (3H, s), 7.35 (2
H, d, J = 8.5Hz), 7.45-7.95 (11H, m).

Reference Example 9 3- (2-benzothiazolylcarbonyl) benzoic acid methyl ester 1.10 g of 3-methoxycarbonylbenzoyl chloride and 1.15 g of 2-trimethylsilylbenzothiazole were dissolved in 30 ml of anhydrous toluene. The mixture was refluxed for 20 hours. After diluting with ethyl acetate, washing with saturated aqueous sodium hydrogen carbonate and saturated saline, drying over anhydrous magnesium sulfate,
The solvent was distilled off. The obtained residue was separated and purified by silica gel column chromatography (elution solvent: cyclohexane / ethyl acetate = 20/1) to obtain 700 mg of the title compound as colorless crystals. Melting point: 132-135 ° C NMR spectrum (CDCl ₃ ) δppm: 3.99 (3H, s), 7.50-
7.75 (3H, m), 8.00-8.80 (4H, m), 9.18 (1H, s).

Reference Example 10 4-Methylthiophenyl-2-benzophenone 1.0 g of 2-bromobenzophenone was dissolved in 10 ml of toluene and 10 ml of ethanol, and stirred at room temperature.
870 mg of 4-methylthiophenylboric acid, 100 m
g of 20% palladium hydroxide-carbon and 10 ml of saturated aqueous sodium hydrogen carbonate were added, and the mixture was heated under reflux for 3.5 hours under a nitrogen stream. The reaction solution was filtered using celite, diluted with ethyl acetate, washed with aqueous potassium hydrogen sulfate and saturated saline, and then
After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. The obtained residue is subjected to silica gel column chromatography (elution solvent: cyclohexane / dichloromethane = 1).
Separation and purification by 9/1) gave 1.36 g of the title compound as a pale yellow oil. NMR spectrum (CDCl ₃ ) δ ppm: 2.40 (3H, s), 7.05-
7.70 (13H, m).

Reference Example 11 N, N-dimethyl- (2-methoxy-4-hydroxy-
5-benzoyl) benzenesulfonamide (11a) (2-methoxy-4-hydroxy-5-benzoyl) benzenesulfonyl chloride 5.0 g of (2-methoxy-4-hydroxy-5-benzoyl) benzenesulfonic acid was added to 100 ml of anhydrous The suspension was suspended in dichloromethane, and 13.7 ml of thionyl chloride and 0.06 ml of anhydrous dimethylformamide were added thereto at room temperature.
For a minute. The mixture was further heated under reflux overnight, and the solvent was distilled off under reduced pressure. The obtained residue was treated with isopropyl ether to give 3.58 g of the title compound as orange crystals. Melting point: 118-126C (decomposition).

(11b) N, N-Dimethyl- (2-methoxy-4-hydroxy-5-benzoyl) benzenesulfonamide 483 mg of dimethylamine hydrochloride was suspended in 50 ml of anhydrous tetrahydrofuran and stirred at room temperature for 1.65 ml.
15 minutes after adding triethylamine of Reference Example (11a)
A solution of 1.29 g of (2-methoxy-4-hydroxy-5-benzoyl) benzenesulfonyl chloride obtained in the above in 10 ml of anhydrous tetrahydrofuran was added dropwise, and 15
For a minute. The solvent was distilled off under reduced pressure, and the obtained residue was diluted with ethyl acetate, washed with 3N aqueous hydrochloric acid, saturated aqueous sodium bicarbonate, and then with saturated saline, and dried over anhydrous magnesium sulfate. Was distilled off. The obtained residue was separated and purified by silica gel column chromatography (elution solvent: cyclohexane / ethyl acetate = 10/1) to obtain 280 mg of the title compound as a colorless foam. NMR spectrum (CDCl ₃ ) δ ppm: 2.82 (6H, s), 4.00 (3
H, s), 6.61 (1H, s), 7.40-7.75 (5H, m), 8.26 (1H, s), 13.0
3 (1H, s).

Reference Example 12 3-Benzoylbenzoic acid benzyl ester 2.262 g of 3-benzoylbenzoic acid was dissolved in 45 ml of anhydrous methyl ethyl ketone, and 2.764 g of anhydrous potassium carbonate and 332 mg of potassium iodide were dissolved at room temperature.
44 ml of benzyl chloride was added and stirred for 24 hours. Further, 1.382 g of anhydrous potassium carbonate, 166 m
g of potassium iodide and 2.1 ml of benzyl chloride were added, and the mixture was heated under reflux for 2 hours. The reaction solution was diluted with ethyl acetate, washed with water and brine, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue is subjected to silica gel column chromatography (eluent:
Separation and purification with cyclohexane / ethyl acetate = 6/1) gave 2.972 g of the title compound as a colorless oil. NMR spectrum (CDCl ₃ ) δppm: 5.39 (2H, s), 7.30-
7.70 (9H, m), 7.80 (2H, d, J = 7.0Hz), 8.01 (1H, d, J = 7.8H
z), 8.29 (1H, d, J = 7.7Hz), 8.49 (1H, s).

Reference Example 13 N-Tosyl-3-benzoylbenzoic acid amide (13a) Potassium p-toluenesulfonamide 856 mg of p-toluenesulfonamide and 561 mg
Of tert-butoxy potassium was dissolved in 8.5 ml of methanol, and the solvent was distilled off under reduced pressure. The obtained residue was treated with ethyl acetate to give 1.025 g of the title compound as colorless crystals. Melting point: 245-248C.

(13b) N-Tosyl-3-benzoylbenzoic acid amide 904 mg of 3-benzoylbenzoic acid was dissolved in 8.5 ml of anhydrous dimethylacetamide, and 0.61 ml of triethylamine was added under ice-cooling and stirring under a nitrogen stream. 0.42m
l of ethyl chloroformate was added and stirred for 1 hour. 8.5m
After adding l of anhydrous dimethylacetamide, 1.004 g of potassium p-toluenesulfonamide obtained in Reference Example (13a) was added, and the mixture was stirred at room temperature for 14 hours. The reaction solution was poured into 100 ml of 0.1N hydrochloric acid and extracted with ethyl acetate. After washing with water, 0.1N sodium hydroxide and saturated saline, the solution was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was treated with ethyl acetate to give the title compound as colorless crystals (980 m).
g was obtained. Melting point: 127 ° C (decomposition) NMR spectrum (d ₆ -DMSO) δppm: 2.31 (3H, s), 7.17
(2H, d, J = 8.0Hz), 7.45-7.85 (9H, m), 8.16 (1H, d, J-7.8H
z), 8.23 (1H, s).

Reference Example 14 6-methoxy-2-methylthiobenzophenone 1.42 g of 6-methoxy-2-methylthiobenzene was dissolved in 20 ml of n-hexane, and 1.50 ml of N, N, N ', N'- Tetramethylethylenediamine was added. Under ice salt cooling and stirring, 6.2 ml of a 1.6 mol solution of n-butyllithium / n-hexane was added dropwise, and the reaction solution was stirred at room temperature for 28 hours. In the reaction solution, under ice salt cooling and stirring,
1. Add 15 ml of benzoyl chloride and add at room temperature.
Stir for 5 hours. Aqueous sodium bicarbonate and ethyl acetate were added, and the ethyl acetate layer was washed with saturated saline, dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was separated and purified by silica gel column chromatography (elution solvent: cyclohexane / ethyl acetate = 50/1 to 10/1) to obtain 601 mg of the title compound as colorless crystals. Melting point: 118-119 ° C NMR spectrum (CDCl ₃ ) δ ppm: 2.37 (3H, s), 3.70 (3
H, s), 6.83 (1H, d, J = 8.3Hz), 7.02 (1H, d, J = 8.0Hz), 7.30
-7.90 (6H, m).

Reference Example 15 (1-Naphthyl)-(2-methylthiophenyl) ketone 10.21 g of 2-methylthiobenzoyl chloride and 3.6
5 g of aluminum chloride was suspended in 20 ml of anhydrous dichloroethane, and a solution of 3.51 g of naphthalene in 7.0 ml of dichloroethane was added dropwise, followed by stirring at room temperature for 2 days. The reaction solution was poured into ice-dilute hydrochloric acid solution and extracted with ethyl acetate. The extract was washed with an aqueous solution of sodium bicarbonate and saturated saline, dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was separated and purified by silica gel column chromatography (elution solvent: cyclohexane / ethyl acetate = 19/1) to obtain 2.34 g of the title compound as a yellow oil. NMR spectrum (d ₆ -DMSO) δppm: 2.47 (3H, s), 7.05
-8.40 (11H, m).

Reference Example 16 2-methylthiophenylboric acid 590 mg of magnesium was suspended in 10 ml of anhydrous tetrahydrofuran, and a solution of 4.70 g of 2-methylthiobromobenzene in 5.0 ml of anhydrous tetrahydrofuran was added dropwise at 60 ° C. under a nitrogen stream. The mixture was heated under reflux for 3 hours. 3.
The above reaction mixture was added dropwise to 41 ml of 20 ml of anhydrous trimethoxyboron at -50 ° C, stirred at room temperature for 2 hours and left overnight. Under ice cooling and stirring, 20 ml of a saturated aqueous potassium bisulfate solution was added, and the mixture was stirred at room temperature for 30 minutes. The reaction solution was poured into water and extracted with ethyl acetate. The extract was washed with water and saturated saline, dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was separated and purified by silica gel column chromatography (elution solvent: cyclohexane: ethyl acetate = 4/1) to obtain 2.03 g of the title compound as colorless crystals. Melting point: 83-85 ° C NMR spectrum (CDCl ₃ ) δ ppm: 2.51 (3H, s), 6.40 (2
H, s), 7.30-7.60 (3H, m), 8.02 (1H, dd, J = 1.5Hz, J = 7.3H
z).

Reference Example 17 2-Methylthiophenyl-2-benzophenone 1.0 g of 2-bromobenzophenone and 870 mg of 2-methylthiophenylboric acid obtained in Reference Example 16 were combined with 2
Suspended in 0 ml of water, 20 mg of palladium acetate and 1.
30 g of anhydrous potassium carbonate and 1.40 g of tetra-n-
Butyl ammonium bromide was added, and the mixture was heated and stirred at 70 ° C. for 17 hours. The reaction solution was filtered using celite, and diluted with ethyl acetate. The ethyl acetate layer was washed with 0.1N hydrochloric acid and saturated saline, dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was separated and purified by silica gel column chromatography (elution solvent: cyclohexane / ethyl acetate = 19/1) to obtain 0.99 g of the title compound as a pale yellow oil. NMR spectrum (CDCl ₃ ) δppm: 2.26 (3H, s), 7.00-
7.75 (13H, m).

Reference Example 18 2-Methylthiophenyl-4-benzophenone 1.0 g of 4-bromobenzophenone and 870 mg of 2-methylthiophenylboric acid obtained in Reference Example 16 were combined with 2 g of 2-methylthiophenyl-4-benzophenone.
Suspended in 0 ml of water, 20 mg of palladium acetate, 1.
30 g of anhydrous potassium carbonate and 1.40 g of tetra-
Add n-butylammonium bromide, and add
The mixture was heated and stirred for an hour. The reaction solution was filtered using Celite,
Diluted with ethyl acetate. The ethyl acetate layer was washed with 0.1N hydrochloric acid and saturated saline, dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was separated and purified by silica gel column chromatography (elution solvent: cyclohexane / ethyl acetate = 19/1) to obtain 0.94 g of the title compound as pale yellow crystals. Melting point: 119-121 ° C NMR spectrum (CDCl ₃ ) δppm: 2.40 (3H, s), 7.20-
7.95 (13H, m).

Reference Example 19 N- (2- (2-methylphenyl) phenylsulfonyl) -3-benzoylbenzamide 452 mg of 3-benzoylbenzoic acid was dissolved in 20 ml of anhydrous N, N-dimethylacetamide and stirred under ice cooling. ,
0.305 ml of triethylamine and 0.21 ml of ethyl chloroformate were added and stirred for 1 hour. On the other hand, 420m
g of 2- (2-methylphenyl) benzenesulfonamide was dissolved in 10 ml of anhydrous N, N-dimethylacetamide, 269 mg of potassium t-butoxide was added, and the mixture was stirred at room temperature for 45 minutes. The two reaction solutions were combined, stirred at room temperature overnight, and further stirred at 50 ° C. for 1 hour. The reaction solution was diluted with ethyl acetate, washed with diluted hydrochloric acid, saturated saline, saturated aqueous sodium bicarbonate, and saturated saline, dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was separated and purified by silica gel column chromatography (elution solvent: cyclohexane / ethyl acetate = 3/1 to 1/3) to obtain 253 mg of the title compound as pale brown crystals. Melting point: 170 ° C. (decomposition) NMR spectrum (d ₆ -DMSO) δ ppm: 1.86 (3H, s), 6.85
-8.15 (17H, m).

Reference Example 20 (2-benzothiazolyl) -3-cyanophenyl ketone 1.0 g of 3-cyanobenzoyl chloride and 1.25
g of 2-trimethylsilylbenzothiazole,
The reaction was carried out in the same manner as in Reference Example 9 and purification was performed to obtain 530 mg of the title compound as yellow crystals. Melting point: 144-145 ° C NMR spectrum (CDCl ₃ ) δppm: 7.55-8.80 (7H, m),
9.02 (1H, s).

Reference Example 21 N- (1-ethylpentyl)-[phenyl- (3-carboxyphenyl) methyl] amine-oxalate (21a) N- (1-ethylpentyl)-[phenyl-
(3-Methoxycarbonylphenyl) methyl] amine 2.337 g of methyl 3-benzoylbenzoate and 2.952 g of 1-ethylpentylamine hydrochloride in 46
dissolved in anhydrous dichloromethane and 6.75 ml of triethylamine and 9.70 under ice-cooling and stirring under a nitrogen stream.
ml of a 1 molar solution of titanium tetrachloride dichloromethane was added and the reaction was stirred at room temperature for 17 hours. The reaction solution was diluted with ethyl acetate, washed with 0.5N aqueous hydrochloric acid and saturated saline, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was dissolved in 56 ml of methanol, 0.74 ml of acetic acid and 2.162 g of sodium cyanoborohydride were added, and the mixture was heated under reflux for 1 hour.
The reaction solution was diluted with ethyl acetate, washed with saturated aqueous sodium hydrogen carbonate, water and saturated saline, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was separated and purified by silica gel column chromatography (elution solvent: cyclohexane / ethyl acetate = 9/1) to obtain 2.584 g of the desired product as a colorless oil. Obtained colorless oil 1
From 36 mg and 36 mg of oxalic acid, 114 mg of the oxalate as the title compound was obtained. Melting point: 70-78 ° C NMR spectrum (d ₆ -DMSO) δppm: 0.84 (6H, t, J = 6.7H
z), 1.10-1.30 (4H, m), 1.40-1.75 (4H, m), 2.55-2.68 (1
H, m), 3.86 (3H, s), 5.58 (1H, s), 7.28-7.70 (6H, m), 7.9
0 (2H, d, J = 7.6Hz), 8.24 (1H, s).

(21b) N- (1-ethylpentyl)-
[Phenyl- (3-carboxyphenyl) methyl] amine oxalate 168 mg of N- (1-ethylpentyl)-[phenyl- (3-methoxycarbonylphenyl) -methyl] amine obtained in Reference Example (21a) After dissolving in 8.1 ml of tetrahydrofuran, 448 mg of potassium tert-butoxide and 18 μl of water were added under ice cooling and stirring, and the reaction solution was stirred at room temperature for 3 hours. Add 4.0 ml of 1 to the reaction solution.
Normal hydrochloric acid is added, the solvent is distilled off under reduced pressure, and the obtained residue is subjected to silica gel column chromatography (elution solvent:
(Methanol / ethyl acetate = 1/1 to 5/1) to give 84 mg of the title compound as an oil. Melting point: 195-197 ° C NMR spectrum (d ₆ -DMSO) δppm: 0.70-0.90 (6H, m),
1.10-1.70 (6H, m), 2.50-2.65 (1H, m), 5.40-5.55 (1H, br.
s), 7.25-7.65 (6H, m), 7.75-7.90 (2H, m), 8.20 (1H, s)
.

Reference Example 22 N- (1-ethylpentyl)-[phenyl- (3-N,
N-dimethylcarbamoylphenyl) methyl] amine 1.383 g of N, N-dimethyl-3-benzoylbenzoate and 1.656 g of 1-ethylpentylamine hydrochloride are dissolved in 28 ml of anhydrous dichloromethane, and cooled with ice in a nitrogen stream. Under stirring, 3.80 ml of a 1 mol solution of triethylamine and 5.50 ml of titanium tetrachloride dichloromethane were added, and the reaction solution was stirred at room temperature for 23 hours. The reaction solution was diluted with ethyl acetate, washed with 0.5N aqueous hydrochloric acid and saturated saline, and dried over anhydrous sodium sulfate.
The solvent was distilled off under reduced pressure. The obtained residue was dissolved in 38 ml of methanol, and 0.47 ml of acetic acid and 1.372 were added.
g of sodium cyanoborohydride was added, and the mixture was heated under reflux for 1 hour. The reaction solution was diluted with ethyl acetate, saturated aqueous sodium hydrogen carbonate,
The extract was washed with water and saturated saline, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was separated and purified by silica gel column chromatography (elution solvent: cyclohexane / ethyl acetate = 1/1) to obtain 1.314 g of the desired product as a colorless oil. NMR spectrum (CDCl ₃ ) δ ppm: 0.75-0.95 (6H, m),
1.10-1.65 (9H, m), 2.30-2.45 (1H, m), 2.92 (3H, s), 3.09
(3H, s), 4.96 (1H, s), 7.10-7.50 (9H, m).

Reference Example 23 N- (1-ethylpentyl)-[phenyl- (3-carbamoylphenyl) methyl] amine oxalate 0.626 g of N- (1-ethylpentyl)-obtained in Reference Example 21 [Phenyl- (3-carboxyphenyl)
-Methyl] amine hydrochloride was dissolved in 12.4 ml of anhydrous dimethylformamide, 0.46 ml of triethylamine and 0.19 ml of ethyl chloroformate were added under ice-cooling and stirring, and the reaction solution was stirred at room temperature for 1 hour. 0.56ml
Was added and stirred at room temperature for 30 minutes. The reaction solution was added to a saline solution, extracted with ethyl acetate, washed with a saturated saline solution, and dried over anhydrous sodium sulfate.
The solvent was distilled off under reduced pressure. The obtained residue is subjected to silica gel column chromatography (elution solvent: cyclohexane /
Separation and purification were performed using ethyl acetate = 1/1) to obtain 0.354 g of a free compound as colorless crystals. Using 0.111 g of the free form, 87 mg of the title compound was obtained as an oxalate. Melting point: 169-173 ° C NMR spectrum (d ₆ -DMSO) δppm: 0.84 (6H, t, J = 7.4H
z), 1.10-1.30 (4H, m), 1.40-1.70 (4H, m), 2.50-2.65 (1
H, m), 5.46 (1H, br.s), 7.20-8.20 (11H, m).

Reference Example 24 N- (1-ethylpentyl)-[phenyl- (3-cyanophenyl) methyl] amine hydrochloride 227 mg of N- (1-ethylpentyl)-[phenyl- (3-carbamoylphenyl)
-Methyl] amine was dissolved in 46 ml of anhydrous dichloromethane, 0.10 ml of phosphorus oxychloride was added under ice-cooling and stirring, the reaction solution was stirred at room temperature for 1 hour, and 0.10 ml of phosphorus oxychloride was added for 1 hour. Stirred. The reaction solution was diluted with ethyl acetate, washed with saturated aqueous sodium hydrogen carbonate, water, and saturated saline, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue is subjected to silica gel column chromatography (elution solvent: cyclohexane / ethyl acetate = 9 /
Separation and purification were performed in 1) to obtain 201 mg of a colorless oil. From the obtained oil (63 mg), 63 mg of the title compound was obtained as a hydrochloride. Melting point: 151-155 ° C NMR spectrum (d ₆ -DMSO) δppm: 0.75-0.95 (6H, m),
1.10-1.35 (4H, m), 1.55-1.95 (4H, m), 2.70-2.90 (1H, m),
5.79 (1H, br.s), 7.35-8.20 (8H, m), 8.34 (1H, s), 9.68
(2H, br.s).

Reference Example 25 N-cyclohexyl- [phenyl- (3-hydroxymethylphenyl) methyl] amine oxalate 323 mg of N-cyclohexyl- [phenyl- (3-methoxycarbonylphenyl) methyl obtained in Reference Example 26 Using an amine and 1.0 ml of a 1 mol solution of lithium aluminum hydride in anhydrous tetrahydrofuran, the reaction was carried out and purified in the same manner as in Example 24 to obtain 307 mg of the title compound as colorless crystals. Melting point: 180-182 ° C NMR spectrum (d ₆ -DMSO) δppm: 0.90-1.80 (8H, m),
2.05-2.22 (2H, m), 2.60-2.75 (1H, m), 4.50 (2H, s), 5.62
(1H, s), 7.20-7.80 (9H, m).

Reference Example 26 N-Cyclohexyl- [phenyl- (3-methoxycarbonylphenyl) methyl] amine As described in Example (2a), using 2.138 g of methyl 3-benzoylbenzoate and 2.04 ml of cyclohexylamine. And purified to give 2.653 g of the title compound as a colorless oil. Melting point: 180-182 ° C NMR spectrum (CDCl ₃ ) δppm: 1.00-1.80 (9H, m),
1.85-2.05 (2H, m), 2.30-2.45 (1H, m), 3.90 (3H, s), 5.08
(1H, s), 7.15-7.45 (6H, m), 7.61 (1H, d, J = 7.8Hz), 7.88
(1H, d, J = 7.8Hz), 8.07 (1H, s).

Reference Example 27 3-Benzoyl-4-fluorobenzonitrile In a solution of 1.0 g of 3-bromo-4-fluorobenzonitrile and 0.58 ml of benzoyl chloride in 20 ml of anhydrous tetrahydrofuran, 3.1 ml of 1.6M n was added.
-Butyl lithium n-hexane solution under a nitrogen atmosphere,
It was added dropwise at 65-66 ° C. After further stirring at -70 ° C for 1 hour, 20 ml of ice was added to the reaction solution, and the temperature was raised to 0 ° C. Dilute the reaction with 100 ml of ethyl acetate,
After separating the aqueous layer, the organic layer was separated from aqueous citric acid, saturated saline,
The extract was washed with saturated aqueous sodium hydrogen carbonate and saturated brine, dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was separated and purified by silica gel column chromatography (elution solvent: cyclohexane / ethyl acetate = 10/1) to obtain 450 mg of the title compound as a white powder. Melting point: 90-92 ° C NMR spectrum (CDCl ₃ ) δppm: 7.32 (1H, dd, J = 8.6H)
z, J = 8.8Hz), 7.52 (2H, m), 7.61 (1H, m), 7.79-7.89 (4H,
m).

Reference Example 28 2,4-Dimethoxy-5-N, N-dimethylsulfamoylbenzophenone In a suspension of 68.3 mg of sodium hydride in 10 ml of anhydrous dimethylformamide, 500 mg of 2-hydroxy-
A solution of 4-methoxy-5-N, N-dimethylsulfamoylbenzophenone in 10 ml of anhydrous dimethylformamide was added dropwise at 3-4 ° C. under a nitrogen atmosphere, and the mixture was stirred at room temperature for 30 minutes. The reaction solution was cooled again, methyl iodide was added dropwise, and the mixture was stirred at room temperature for 15 hours. Reaction solution 15
Dilute with 0 ml of ethyl acetate, wash with saturated aqueous sodium bicarbonate, saturated saline, 3N-hydrochloric acid, saturated saline, aqueous sodium thiosulfate, saturated saline, saturated aqueous sodium bicarbonate, and saturated brine, and then with anhydrous magnesium sulfate. It was dried and the solvent was distilled off under reduced pressure. The resulting residue was triturated with diisopropyl ether to give the title compound as a pale yellow powder (41).
0 mg was obtained. Melting point: 148-150 ° C NMR spectrum (CDCl ₃ ) δ ppm: 2.84 (6H, s), 3.83 (3
H, s), 4.02 (3H, s), 6.56 (1H, s), 7.44 (2H, dd, J = 7.3Hz, J
= 7.9Hz), 7.57 (1H, t, J = 7.2Hz), 7.76 (2H, dd, J = 1.7Hz, J =
8.5Hz), 7.96 (1H, s).

Test Example 1 Measurement of Intestinal Bile Acid Transporter Inhibitory Activity Using Caco-2 Cells The measurement of ileal bile acid transporter inhibitory activity in this test example was performed according to [J. Biol. Chem., 269, 1340]. -1347 (199
4)], according to the method of Wong et al. That is, Caco-2 cells described in [Am. J. Physiol., 264, G1118-G1125 (1993)] were used as cells expressing the bile acid transporter. After 200 μl of 4 × 10 ⁴ / ml Caco-2 cells were seeded in each well of a collagen-coated 96-well culture plate (trade name: View plate, manufactured by Packard), the medium was appropriately changed for 15 days or more and cultured. did. After adding the specimen (compounds of Examples 1, 11 and 15) to the main culture system, 0.1 ml of the specimen was added.
1 μCi of radioactive taurocholic acid ([ ³ H] -taurocho
lic acid: NEN) in the presence of 5% CO ₂
Incubate at 7 ° C. for 1 hour, and radioactive taurocholate is added to Caco-2 by ileal bile acid transporter.
Cells were taken up. Caco-2 cells were ice-cooled with 0.2% bovine serum albumin,
PBS (phosphat) containing 1 mM taurocholic acid (cold)
e buffered saline) and left to dry overnight. 250 μl per well of a 96-well culture plate
Liquid scintillation cocktail (trade name: Micros)
cint20 (manufactured by Packard) was added, and the radioactivity was measured by a top count (manufactured by Packard) which is a type of liquid scintillation counter. The inhibition rate (%) was determined from the radioactivity of the control obtained without using the test compound and the radioactivity when the test compound was used at a certain concentration, and the concentration of the test compound that inhibited the ileal bile acid transporter activity by 50%. Was examined. Table 4 shows the results.

[0308]

[Table 4] Example Compound No. IC ₅₀ (μg / ml) 32 (Isomer A) 1.2 32 (Isomer B) 0.8 37 2.9 42 (Isomer B) 2.1 51 (Isomer B) 1.3 .

Test Example 2 Measurement of Intestinal Bile Acid Transporter Inhibitory Activity Using Rat Everted Ileal Rings The measurement of ileal bile acid transporter inhibitory activity in this test example was performed using [Pharm. Res. , 12, 693-699 (1995)], according to the method of Stewart et al. That is, a rat inverted intestinal ring was used as a material for the bile acid transporter. Male Wistar Imamichi rats of 6 to 10 weeks of age are anesthetized with ether, the ileum is removed about 20 cm from the blind end, inverted, and then cut in ice-cold Ringer's buffer in 5 mm steps from the blind end. 24
One rat inverted intestinal ring was obtained. To correct for differences in bile acid transporter expression levels depending on the site of the ileum,
Rings were appropriately selected from the top and bottom of the ileum, and four rings were used as a group to form a total of six groups. Each ring was placed in 1 ml of radioactive taurocholic acid solution at 37 ° C. for 3 minutes at 90 rpm.
The ring was loaded with radioactive taurocholic acid by an ileal bile acid transporter while shaking at a speed of m. The composition of the radioactive taurocholic acid solution is 1.0 μCi
It consists of radioactive taurocholic acid, 0.037 mM taurocholic acid (cold), various analytes at appropriate concentrations and Ringer's buffer. After the ring was washed three times with Ringer's buffer solution, the wet weight was measured, and placed in a vial.
0.5 ml of CS-II (manufactured by AMERSHAM) was added and left at 50 ° C. overnight to completely dissolve. 2.5m
One liter of liquid scintillation cocktail was added and the radioactivity was measured on a liquid scintillation counter. The ileal bile acid transporter activity was determined by correcting each radioactivity by wet weight, dpm / mg
(Radioactivity per 1 mg), the average value of each group was defined as the activity, and the concentration of the test compound was 100 μg / ml.
The inhibition rate of the ileal bile acid transporter activity was determined. Table 5 shows the results.

[0310]

[Table 5] Example compound number Inhibition rate (%) 172 42 (Isomer B) 77 .

Formulation Example 1 Tablets Compound of Example 1 10 mg Lactose 68.5 Crystalline Cellulose 20 Carboxymethyl starch Sodium 5 Light Silicic Anhydride 0.5 Magnesium stearate 1 105 mg

[0312]

Industrial Applicability The compound of the present invention having the above general formula (I) or a pharmaceutically acceptable salt thereof has an excellent ileal bile acid transporter inhibitory activity, and exhibits hyperlipidemia or arteriosclerosis. It is useful as a therapeutic or prophylactic agent.

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁷ Identification symbol FI Theme coat ゛ (Reference) A61K 31/185 A61K 31/185 4C086 31/381 31/38 601 4C204 31/40 31/40 4C206 31/404 607 4H006 31/41 31/41 31/421 31/42 601 31/423 603 31/426 31/425 601 31/428 603 C07C 237/30 C07C 237/30 237/34 237/34 309/32 309/32 309/42 309/42 311/08 311/08 311/51 311/51 311/54 311/54 317/34 317/34 // C07D 207/335 C07D 207/335 209/14 209/14 257/04 257 / 04 E 263/32 263/32 263/56 263/56 277/28 277/28 277/64 277/64 333/20 333/20 333/48 333/48 333/58 333/58 403/10 403 / 10 409/10 409/10 413/10 413/10 417/10 417/10 (72) Inventor Eiichi Masuko 2-58, Hiromachi, Shinagawa-ku, Tokyo Sankyo Co., Ltd. (72) Inventor Kono Keita 1-258 Hiromachi, Shinagawa-ku, Kyoto F-term (reference) 4C023 CA01 4C033 AD06 AE03 AE06 4C056 AA01 AB01 AC02 AD01 AD03 AE03 BA11 CA09 CC01 CD01 FA01 FB01 4C063 AA01 BB09 CC47 CC52 CC62 CC94 DD06 4C069 AC02 BB03 BB34 4C086 AA01 AA02 BB02 BB03 BC05 BC13 BC62 BC69 BC70 BC82 BC84 GA04 GA07 GA09 GA10 MA01 MA04 NA14 ZA45 ZC33 4C204 BB01 CB02 DB13 EB02 EB03 FB01 GB01 GB03 4C206 AA01 A04A01 MA08 AA03 AB23 AC11 AC52 AC53 AC62 BU38 BU46 BU48 TA02 TB02 TB04 TC37

Claims (25)

[Claims] 1. A compound of the general formula [Wherein, R ¹ represents a C ₆ -C ₁₀ aryl group substituted by 1 to 3 groups with a group selected from substituent group α, a tetrazolyl group optionally substituted with a group selected from substituent group β] , (C
_3- C ₆ cycloalkyl) carbamoyl group, (C ₁ -C
_{6 to 6} alkyl) sulfonylcarbamoyl groups, one to three of which may be substituted with a group selected from substituent group δ (C ₆ −
C ₁₀ aryl) sulfonylcarbamoyl group, a sulfo group,
A C ₁ -C ₆ alkylsulfonyl group, a C ₆ -C ₁₀ arylsulfonyl group which may be substituted by 1 to 3 groups selected from a substituent group β, a mono- (C ₁ -C ₆ alkyl) aminosulfonyl group A C ₇ -C ₁₁ arylcarbonyl which may be substituted by 1 to 3 groups selected from a di- (C ₁ -C ₆ alkyl) aminosulfonyl group, a C ₁ -C ₆ alkylsulfinyl group and a substituent group β Amino group, tetrazolylcarbonylamino group which may be substituted with a group selected from substituent group β, or 1 to 3 groups which may be substituted with a group selected from substituent group β (C ₆ -C ₁₀ Aryl) sulfonylcarbamoylamino group, wherein R ² , R ³ and R ⁴ are the same or different and are a hydrogen atom, a C ₁ -C ₆ alkyl group, a C ₁ -C ₆ alkoxy group,
Hydroxyl group, halogen atom, amino group, mono- (C ₁ -C ₆
Alkyl) amino group or di- (C ₁ -C ₆ alkyl)
An amino group; R ⁵ is a C ₆ -C ₁₀ aryl group which may be substituted by 1 to 3 groups selected from substituent group β or 1 to 3 groups selected from substituent group β; Represents a thienyl, pyrrolyl, 1,1-dioxothienyl, thiazolyl or oxazolyl group which may be substituted or condensed with a benzene ring; R ⁶ represents a C ₁ -C ₁₀ alkyl group; ⁷ [where
W represents a single bond or a C ₁ -C ₆ alkylene group;
⁷ is a C ₃ -C ₆ cycloalkyl group which may be substituted with 1 to 3 groups selected from the substituent group γ and may be condensed with a benzene ring. Or a C ₇ -C which may be substituted by 1 to 3 groups selected from a group selected from the substituent group γ
_{16 represents an} aralkyl group. ], Or an ileal bile acid transporter inhibitor comprising a benzylamine or a pharmacologically acceptable salt thereof as an active ingredient. <Substituent group α> A tetrazolyl group, a sulfo group, a C ₁ -C ₆ alkylsulfonyl group, a C ₁ -C ₆ alkylsulfonylamino group, and a substituent group β which may be substituted with a group selected from the substituent group β C ₆ -C ₁₀ arylsulfonylamino group which may be substituted by 1 to 3 groups selected from <substituent group β> C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group and halogen atom <substitution Group γ> C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halogen atom and formula -ZR ⁸ [wherein Z
Is a single bond or C ₁ -C ₆ alkylene group, R ⁸
The carboxy group, C ₂ -C ₇ alkoxycarbonyl group, a carbamoyl group, a mono - (C ₁ -C ₆ alkyl) carbamoyl group, di - (C ₁ -C ₆ alkyl) carbamoyl group, C ₁ -C ₆ alkylsulfonyl Group or hydroxyl group. <Substituent group δ> a C ₁ -C ₆ alkyl group, a C ₁ -C ₆ alkoxy group, a halogen atom and a phenyl group which may be substituted by 1 to 3 groups selected from a substituent group β. . 2. The method according to claim 1, wherein R ¹ is a substituent group α1.
A phenyl group substituted with a group selected from the group consisting of
A tetrazolyl group which may be substituted with a group selected from 1, a (C ₅ -C ₆ cycloalkyl) carbamoyl group,
(C ₁ -C ₄ alkyl) sulfonylcarbamoyl group, phenylsulfonylcarbamoyl group which may be substituted with a group selected from substituent group δ1, sulfo group, C ₁ -C ₆ alkylsulfonyl group, substituent group β1 A phenylsulfonyl group, a methylaminosulfonyl group, an ethylaminosulfonyl group, a dimethylaminosulfonyl group, a diethylaminosulfonyl group, a C ₁
-C ₄ alkylsulfinyl group, phenyl which may be substituted with a group selected from substituent group β2, phenylcarbonylamino or tetrazolylcarbonylamino group which may be substituted with a group selected from substituent group β1 An ileal bile acid transporter inhibitor comprising, as an active ingredient, a benzylamine which is a sulfonylcarbamoylamino group or a pharmacologically acceptable salt thereof. <Substituent group α1> Tetrazolyl group, sulfo group, C ₁ -C ₄ alkylsulfonyl group, methylsulfonylamino group, ethylsulfonylamino group and substituent group β2 which may be substituted with a group selected from substituent group β2 Phenylsulfonylamino group which may be substituted with a group selected from <substituent group β1> C ₁ -C ₄ alkyl group, C ₁ -C ₄ alkoxy group, fluorine atom and chlorine atom <substituent group β2> C ₁ —C ₂ alkyl group, C ₁ -C ₂ alkoxy group, fluorine atom and chlorine atom <Substituent group δ1> selected from C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, halogen atom and substituent group β 1 A phenyl group which may be substituted with a group; 3. The method according to claim 1, wherein R ¹ is 2-, 3- or 4- (1H-tetrazol-5-yl) phenyl, 2-, 3- or 4- (1-methyltetrazole-5). Yl) phenyl group, 2-, 3- or 4- (1
-Methoxytetrazol-5-yl) phenyl group, 2
-, 3- or 4- (1-fluorotetrazole-5
-Yl) phenyl group, 2-, 3- or 4- (1-chlorotetrazol-5-yl) phenyl group, 2-, 3-
Or 4-methylsulfonylphenyl group, 2-, 3-
Or 4-ethylsulfonylphenyl group, 2-, 3-
Or 4-propylsulfonylphenyl group, 2-, 3
-Or 4-butylsulfonylphenyl group, 2-, 3
-Or 4-methylsulfonylaminophenyl group, 2
-, 3- or 4-phenylsulfonylaminophenyl group, a tetrazolyl group optionally substituted with a group selected from the substituent group β2, a (C ₁ -C ₂ alkyl) sulfonylcarbamoyl group, and a substituent group δ2 that optionally substituted phenylsulfonyl be carbamoylmethyl group group, C ₁
-C ₄ alkylsulfonyl group, substituted with a group selected from Substituent group β2 is an optionally phenylsulfonyl group, C ₁
-C ₂ alkylsulfinyl group, phenyl which may be substituted with a group selected from substituent group β3, phenylcarbonyl which may be substituted with a phenylcarbonylamino or tetrazolylcarbonylamino group or a group selected from substituent group β2 An ileal bile acid transporter inhibitor comprising, as an active ingredient, a benzylamine which is a sulfonylcarbamoylamino group or a pharmacologically acceptable salt thereof. <Substituent group β2> C ₁ -C ₂ alkyl group, C ₁ -C ₂ alkoxy group, fluorine atom and chlorine atom <Substituent group β3> Methyl group, methoxy group, fluorine atom and chlorine atom <Substituent group δ2> A C ₁ -C ₂ alkyl group, a C ₁ -C ₂ alkoxy group, a fluorine atom, a chlorine atom and a phenyl group which may be substituted with a group selected from the substituent group β2. 4. The method according to claim 1, wherein R ¹ is 2-, 3- or 4- (1H-tetrazol-5-yl) phenyl, 2-, 3- or 4-methylsulfonylphenyl, 3- or 4-ethylsulfonylphenyl group, a tetrazolyl group optionally substituted with a group selected from substituent group β2, a phenylsulfonylcarbamoyl group optionally substituted with a group selected from substituent group δ3, methylsulfonyl Group, ethylsulfonyl group, propylsulfonyl group, butylsulfonyl group, phenylsulfonyl group which may be substituted with a group selected from the group of substituents β3 or phenylsulfonylcarbamoylamino group which may be substituted (the substituent is C ₁ -C ₂ alkyl, methoxy, fluorine or chlorine) and a benzyl amine or a pharmacologically acceptable effective salt An ileal bile acid transporter inhibitor contained as a component. <Substituent group β2> C ₁ -C ₂ alkyl group, C ₁ -C ₂ alkoxy group, fluorine atom and chlorine atom <Substituent group β3> Methyl group, methoxy group, fluorine atom and chlorine atom <Substituent group δ3> A methyl group, a methoxy group, a fluorine atom, a chlorine atom and a phenyl group which may be substituted by C ₁ -C ₂ alkyl, methoxy, fluorine or chlorine. 5. The method according to claim 1, wherein R ¹ is substituted with a group selected from 2-methylsulfonylphenyl, 3-methylsulfonylphenyl, 4-methylsulfonylphenyl, and substituent group β3. Phenylsulfonylcarbamoyl, phenylsulfonylcarbamoyl, methylsulfonyl, ethylsulfonyl, butylsulfonyl, phenylsulfonyl or phenylsulfonylcarbamoylamino which may be substituted with a tetrazolyl group, a group selected from substituent group δ4 An ileal bile acid transporter inhibitor comprising, as an active ingredient, a benzylamine group or a pharmacologically acceptable salt thereof. <Substituent group β3> Methyl group, methoxy group, fluorine atom and chlorine atom <Substituent group δ4> Methyl group, phenyl group and methylphenyl group. 6. The method of claim 1, wherein R ¹ is a 1H-tetrazol-5-yl group, a methylsulfonyl group, an ethylsulfonyl group or a tosylcarbamoylamino group, or a pharmaceutically acceptable salt thereof. An ileal bile acid transporter inhibitor contained as a component. 7. The ileal bile acid transporter inhibitor according to claim 1, wherein R ¹ is a 1H-tetrazol-5-yl group benzylamine or a pharmacologically acceptable salt thereof as an active ingredient. 8. One of the first to seventh aspects
Wherein R ² , R ³ and R ⁴ are the same or different and are a hydrogen atom, a C ₁ -C ₂ alkyl group, a C ₁ -C ₂ alkoxy group, a hydroxyl group, a fluorine atom, a chlorine atom, an amino group,
A mono- (C ₁ -C ₂ alkyl) amino group or di- (C
₁ -C ₂ alkyl) ileal bile acid transporter inhibitor containing salt as an active ingredient to be benzylamines or a pharmacologically acceptable amino group. 9. One of the first to seventh aspects
Wherein R ² , R ³ and R ⁴ are the same or different and are a hydrogen atom, a methyl group, a methoxy group, a hydroxyl group, a fluorine atom or a chlorine atom, or a pharmacologically acceptable salt thereof as an active ingredient. Ileal bile acid transporter inhibitor. 10. A benzylamine according to claim 1, wherein R ² is a hydrogen atom, a methoxy group or a fluorine atom, and R ³ and R ⁴ are hydrogen atoms, or a pharmaceutically acceptable salt thereof. An ileal bile acid transporter inhibitor comprising an acceptable salt as an active ingredient. 11. The method according to claim 1, wherein R ² , R ³ and R ⁴ are hydrogen atoms, such as benzylamines or pharmacologically acceptable salts thereof. Ileal bile acid transporter inhibitor. 12. The method according to claim 1, wherein R ⁵ is phenyl, naphthyl, thienyl, 1,1-, which may be substituted with a group selected from the group of substituents β1. An ileal bile acid transporter inhibitor comprising, as an active ingredient, benzylamines which are dioxothienyl, thiazolyl, benzothienyl, 1,1-dioxobenzothienyl or benzothiazolyl group or a pharmacologically acceptable salt thereof. <Substituent group β1> C ₁ -C ₄ alkyl group, C ₁ -C ₄ alkoxy group, fluorine atom and chlorine atom. 13. The phenyl, thienyl, thiazolyl, benzothienyl or 1,1-dioxobenzothienyl group according to claim 1, wherein R ⁵ may be substituted with a group selected from the substituent group β2. An ileal bile acid transporter inhibitor comprising, as an active ingredient, a benzylamine or a pharmacologically acceptable salt thereof. <Substituent group β2> C ₁ -C ₂ alkyl group, C ₁ -C ₂ alkoxy group, fluorine atom and chlorine atom. 14. The method according to claim 1, wherein R ⁵ is a phenyl group, a benzothienyl group, or a 1,1-substituent, which may be substituted with a group selected from the substituent group β3. An ileal bile acid transporter inhibitor comprising, as an active ingredient, benzylamines which are dioxobenzothienyl groups or a pharmacologically acceptable salt thereof. <Substituent group β3> Methyl group, methoxy group, fluorine atom and chlorine atom. 15. The method according to claim 1, wherein R ⁵ is phenyl, 2-, 3- or 4-methoxyphenyl, 2,3-dimethoxyphenyl, 2,4-dimethoxyphenyl. , 3,4-dimethoxyphenyl, 3,5-dimethoxyphenyl or 3,4
An ileal bile acid transporter inhibitor comprising, as an active ingredient, a benzylamine which is a 5-trimethoxyphenyl or 1,1-dioxobenzothiophen-3-yl group or a pharmacologically acceptable salt thereof. 16. A benzylamine according to any one of claims 1 to 11, wherein R ⁵ is phenyl or a 2-, 3- or 4-methoxyphenyl group, or a pharmacologically acceptable salt thereof. An ileal bile acid transporter inhibitor comprising, as an active ingredient. 17. The ileal bile acid trans-compound according to any one of claims 1 to 11, wherein R ⁵ is a phenyl group benzylamine or a pharmacologically acceptable salt thereof as an active ingredient. Porter inhibitor. 18. The method according to claim 1, wherein R ⁶ is a C ₃ -C ₈ alkylene group, a formula —WR ⁷ [wherein W is a single bond or C ₁ -C ₂ alkylene group, wherein R ⁷ is a C ₅ alkyl group which may be substituted with a group selected from substituent group γ 1 and may be condensed with a benzene ring.
—C ₆ cycloalkyl group. Or an aralkyl group (the aryl part is a phenyl group and the alkyl part is a C ₁ -C ₄ alkyl group) which may be substituted with a group having the formula An ileal bile acid transporter inhibitor comprising a pharmacologically acceptable salt thereof as an active ingredient. <Substituent group γ1> C ₁ -C ₂ alkyl group, t-butyl group, C ₁ -C ₂ alkoxy group, fluorine atom, chlorine atom and formula -ZR ^{8 wherein} Z is a single bond or C ₁ -C ₂
R ⁸ is carboxy, C ₂ -C ₃
Alkoxycarbonyl, carbamoyl, mono- (C _1-
C ₂ alkyl) carbamoyl, di - (C ₁ -C ₂ alkyl) carbamoyl group having a C ₁ -C ₄ alkylsulfonyl or a hydroxyl group. 19. The compound according to any one of claims 1 to 17, wherein R ⁶ is a C ₃ -C ₈ alkylene group or a group having the formula —WR ^{7 wherein} W is a single bond or a methylene group, R ⁷ is may be fused with good benzene ring substituted with a group selected from substituent group .gamma.2 C ₅ -
It is a C ₆ cycloalkyl group. Or an aralkyl group which may be substituted with a group selected from the substituent group γ2 (the aryl part is a phenyl group and the alkyl part is C ₁ -C ₄
It is an alkyl group. Or an ileal bile acid transporter inhibitor comprising, as an active ingredient, a benzylamine or a pharmacologically acceptable salt thereof. <Substituent group γ2> A methyl group, a t-butyl group, a methoxy group, a fluorine atom, a chlorine atom, a carboxy group, a methoxycarbonyl group, a dimethylcarbamoyl group and a hydroxymethyl group. 20. The method according to claim 1, wherein R ⁶ is selected from the group consisting of isopropyl group, butyl group, t-butyl group, neopentyl group, 1-ethylpentyl group, 2-ethylhexyl group and substituent group γ3. May be replaced by
An ileal bile acid transporter inhibitor comprising, as an active ingredient, a benzylamine which is a cyclohexyl, benzyl, 1-phenylethyl or 2-phenylethyl group or a pharmacologically acceptable salt thereof. <Substituent group γ3> Methyl group, methoxy group, fluorine atom and chlorine atom. 21. The benzylamine according to any one of claims 1 to 17, wherein R ⁶ is 1-ethylpentyl, cyclohexyl or 1-phenylethyl, or a pharmacologically acceptable one thereof. An ileal bile acid transporter inhibitor containing a salt as an active ingredient. 22. The method according to claim 1, wherein R ⁶ is 1-ethylpentyl or 1-phenylethyl, or a pharmaceutically acceptable salt thereof. An ileal bile acid transporter inhibitor contained as a component. 23. The ileal bile acid transporter inhibitor according to claim 1, which comprises, as an active ingredient, any one compound selected from the following or a pharmacologically acceptable salt thereof. N- (1-phenylethyl)-{phenyl- [6-hydroxy-4-methoxy-2- (1H-tetrazol-5)
-Yl) phenyl] methyl} amine, N- (1-ethylpentyl)-{phenyl- [3- (1
H-tetrazol-5-yl) phenyl] methyl} amine; N- (1-phenylethyl)-{phenyl- [3- (1
H-tetrazol-5-yl) phenyl] methyl} amine; N- (1-ethylpentyl)-{phenyl- [4- (1
H-tetrazol-5-yl) phenyl] methyl} amine; N- (1-phenylethyl)-{phenyl- [4- (1
H-tetrazol-5-yl) phenyl] methyl} amine; N- (1-phenylethyl)-{(4-methoxyphenyl)-[4- (1H-tetrazol-5-yl) phenyl] methyl @Amine, N- (1-phenylethyl)-[phenyl- (3-methylsulfonylcarbamoylphenyl) methyl] amine, N- (1-ethylpentyl)-[phenyl- (3-N-
Tosylcarbamoylphenyl) methyl] amine, N-cyclohexyl- [phenyl- (3-N-tosylcarbamoylphenyl) methyl] amine, N- (1-phenylethyl)-[phenyl- (3-N-
Tosylcarbamoylphenyl) methyl] amine, N- (1-phenylethyl)-{phenyl- [3- (2
-(2-methylphenyl) phenyl) sulfonylcarbamoylphenyl] methyl} amine, N- (1-phenylethyl)-{phenyl- [3- (2
-(3-methylphenyl) phenyl) sulfonylcarbamoylphenyl] methyl} amine, N- (1-phenylethyl)-{phenyl- [3- (2
-(4-methylphenyl) phenyl) sulfonylcarbamoylphenyl] methyl} amine, N- (1-phenylethyl)-{phenyl- [4- (2
-(2-methylphenyl) phenyl) sulfonylcarbamoylphenyl] methyl} amine, N- (1-phenylethyl)-{phenyl- [4- (2
-(4-methylphenyl) phenyl) sulfonylcarbamoylphenyl] methyl} amine, N- (1-ethylpentyl)-[phenyl- (2-ethylsulfonylphenyl) methyl] amine, N- (indan-1-yl)- [Phenyl- (2-ethylsulfonylphenyl) methyl] amine, N- (2-phenylethyl)-[phenyl- (2-ethylsulfonylphenyl) methyl] amine, N-tert-butyl- [phenyl- (2-phenyl) Sulfonylphenyl) methyl] amine, N- {2- [1-phenyl-1- (N-1-phenylethyl) amino] methyl} phenyl-N'-tosylurea, N- {2- [1- (4-methoxy) Phenyl) -1- (N
-1-phenylethyl) amino] methyl @ phenyl-
N'-tosylurea, N- (1-ethylpentyl)-{2-indenyl- [3
-(1H-tetrazol-5-yl) phenyl] methyl} amine, N- (1-phenylethyl)-{2-indenyl- [4
-(1H-tetrazol-5-yl) phenyl] methyl} amine, N- (1-ethylpentyl)-{1-naphthyl- [3-
(1H-tetrazol-5-yl) phenyl] methyl}
Amine, N- (1-phenylethyl)-{1-naphthyl- [3-
(1H-tetrazol-5-yl) phenyl] methyl}
Amine, N- (1-phenylethyl)-{1-naphthyl- [4-
(1H-tetrazol-5-yl) phenyl] methyl}
Amine, N- [1- (4-bromophenyl) ethyl]-{(1,
1-dioxothiophen-2-yl)-[3- (1H-
Tetrazol-5-yl) phenyl] methyl} amine, N- (1-ethylpentyl)-{2-thiazolyl- [3
-(1H-tetrazol-5-yl) phenyl] methyl} amine, N- (1-phenylethyl)-{3-thiazolyl- [3
-(1H-tetrazol-5-yl) phenyl] methyl} amine, N- (1-phenylethyl)-{2-indolyl- [3
-(1H-tetrazol-5-yl) phenyl] methyl} amine, N- [1- (4-bromophenyl) ethyl]-{2-indolyl- [3- (1H-tetrazol-5-yl) ) Phenyl] methyldiamine, N-cyclohexyl-[(1,1-dioxybenzothiophen-3-yl)-(2-methylsulfonylphenyl) methyl] amine, N- [1- (4-bromophenyl) ethyl ]-｛(1,
1-dioxybenzothiophen-2-yl)-[3-
(1H-tetrazol-5-yl) phenyl] methyl}
Amine, N- [1- (4-bromophenyl) ethyl]-{2-benzothiazolyl- [3- (1H-tetrazol-5-yl) phenyl] methyl} amine or N- (1-phenylethyl)- {3-benzoxazolyl- [3- (1H
An ileal bile acid transporter inhibitor comprising -tetrazol-5-yl) phenyl] methyldiamine as an active ingredient. 24. A therapeutic or prophylactic agent for hyperlipidemia, comprising as an active ingredient the benzylamines or a pharmacologically acceptable salt thereof according to any one of claims 1 to 23. 25. A therapeutic or prophylactic agent for arteriosclerosis, comprising as an active ingredient a benzylamine or a pharmaceutically acceptable salt thereof according to any one of claims 1 to 23.