JP2005206492A - Sulfonamide compound - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide an excellent acyl coenzyme A: diacylglycerol acyl transferase inhibitor useful for obesity, hyperlipemia, diabetes, and the like. <P>SOLUTION: This acyl coenzyme A: diacylglycerol acyl transferase inhibitor containing a sulfonamide compound having the general formula (I) [A<SP>1</SP>is a substitutable alkyl; a substitutable phenylalkyl; a substitutable phenoxyalkyl; substitutable indanyl, indenyl, tetrahydronaphthyl, dihydronaphthyl; or a substitutable heterocyclyl; A<SP>2</SP>is a substitutable alkyl, a substitutable dialkylaminoalkyl; a substitutable alkylthioalkyl; substitutable indanyl, indenyl, tetrahydronaphthyl, dihydronaphthyl; a substitutable five- or six-membered aromatic heterocyclyl or the like; A<SP>3</SP>is a substitutable phenylalkyl; substitutable naphthylmethyl; substitutable phenyl; substituted phenyl; substitutable naphthyl; a substitutable five- or six-membered aromatic heterocyclyl or the like] or its pharmacologically acceptable salt as an active ingredient. <P>COPYRIGHT: (C)2005,JPO&NCIPI

Description

The present invention relates to an acyl coenzyme A: diacylglycerol acyltransferase (hereinafter also referred to as DGAT) inhibitor containing a sulfonamide compound having a specific chemical structure or a pharmacologically acceptable salt thereof, and And a sulfonamide compound having a specific chemical structure having an excellent acylcoenzyme A: diacylglycerol acyltransferase inhibitory activity or a pharmacologically acceptable salt thereof.

  In obesity, triglycerides (triacylglycerol or triglyceride, TG) accumulate in adipocytes due to the persistence of excess energy compared to energy consumption, resulting in a normal body weight. (Eiji Itagaki, “STEP metabolism and endocrine”, Kaiba Shobo, 1st edition, 1998, p. 105). Obesity is hyperlipidemia, hyperTG, diabetes, hypertension, arteriosclerosis and other lifestyle-related diseases, cerebrovascular disorders, coronary artery disease, respiratory abnormalities, low back pain, knee osteoarthritis, gout, cholelithiasis, etc. Any obesity that has these complications or that may cause these complications in the future is defined as obesity and is treated as a disease.

  In recent years, obesity has been shown to be one of the main causes of lifestyle-related diseases called metabolic syndrome (Zimmet, P. et al., Nature, 2001, 414, p. 782). -787). In obese individuals, accumulated visceral fat releases factors such as fatty acids and TNF-α, which cause insulin resistance in skeletal muscle, liver and adipose tissue, and promotes synthesis of neutral fat in the liver. It has been reported to cause hyperlipidemia. In addition, elevated blood insulin levels caused by insulin resistance cause impaired glucose tolerance and diabetes, and also increase peripheral vascular resistance through increased Na ion reabsorption and activation of sympathetic nerves in the kidney, Causes hypertension. Hyperlipidemia, diabetes and hypertension caused by obesity are thought to cause cerebrovascular disorders such as arteriosclerosis and vascular disorders such as coronary artery disease, resulting in serious life-threatening conditions. Yes.

  Currently used anti-obesity drugs include mazindol (Engstrom, RG et al., (1975) Arch. Intern. Pharmacodyn., 1975, 214, p.308-321), sibutramine (Bray, GA et al. al., Obes. Res., 1996, Vol. 4, p.263-270) and other central appetite suppressants and pancreatic lipase inhibitors such as orlistat are known. However, with central appetite suppressants, side effects such as dry mouth, constipation, stomach discomfort, and sometimes hallucinations and visual hallucinations have been observed in orlistat (Davidson, MH et al., The Journal of the American Medical Association, 1999, Vol. 281). , p.235-242), side effects in the gastrointestinal tract such as diarrhea, incontinence, fatty stool, and defecation may occur, and the development of effective drugs with fewer side effects is desired.

  Animals and plants store lipids as insoluble TGs and break down TGs to produce energy as needed. TG ingested by meals is broken down into free fatty acids and monoacylglycerol by the action of bile acids and pancreatic lipase in the lumen of the small intestine. Micelles composed of free fatty acid, monoacylglycerol and bile acid are absorbed into small intestinal epithelial cells, and in the endoplasmic reticulum, acylcoenzyme A synthase (hereinafter referred to as ACS), acylcoenzyme A: monoacylglycerol acyltransferase (hereinafter referred to as MGAT) ) And DGAT, TG is newly synthesized. TG, in combination with phospholipids, cholesterol and apolipoprotein, is secreted into the gastrointestinal lymphatic vessels as kilomicrons. Furthermore, TG is secreted into the blood via the lymph main duct and is transported to the periphery for use. On the other hand, in adipose tissue, TG is synthesized from glycerol 3-phosphate and free fatty acid by the action of ACS, glycerol 3-phosphate acyltransferase, lysophosphatidic acid acyltransferase and DGAT (Coleman, R., Bell, R., J. Biol. Chem., 1976, Vol. 251, p.4537-4543). Thus, TG ingested excessively accumulates in adipose tissue, resulting in obesity.

  DGAT is an enzyme that is present in the endoplasmic reticulum in the cell and catalyzes the most important final step of the TG synthesis pathway, ie, the reaction of transferring the acyl group of acylcoenzyme A to the 3-position of 1,2-diacylglycerol. (Coleman, R., Methods in Enzymology, 1992, 209, p. 98-104; Lehner, R., Kuksis, A., Prog. Lipid Res., 1996, 35, p.169-201; R. Bell., Ann. Rev. Biochem., 1980, vol. 49, p.459-487). DGAT includes two isozymes DGAT1 (Cases, S. et al., Proc. Natl. Acad. Sci. USA., 1998, Vol. 95, p.13018-13023) and DGAT2 (Cases, S. et al. al., J. Biol. Chem., 2001, 276, pp. 38870-38876), and the differences in their roles have been clarified only slightly. It has been suggested that there is a relationship between obesity, lipid metabolism, sugar metabolism and the like. DGAT is a key enzyme for TG synthesis in gastrointestinal epithelial cells and adipose tissue, and drugs that inhibit DGAT suppress fat absorption in the gastrointestinal tract and fat accumulation in adipose tissue by inhibiting TG synthesis, obesity , Obesity, hyperlipidemia, hyperTGemia, dyslipidemia, insulin resistance syndrome, diabetes, or hyperlipidemia caused by obesity, hyperTGemia, dyslipidemia, insulin resistance It is expected to be useful as a therapeutic or prophylactic agent for syndrome, diabetes, hypertension, arteriosclerosis, cerebrovascular disorder, or coronary artery disease (Smith, SJ et al., Nat. Genet., 2000, 25, p.87-90; Chen, HC, J. Clin. Invest., 2002, 109, p.1049-1055; Buhman, KK, J. Biol. Chem., 2002, 277 Vol., P.25474-25479; Gaziano, J., et al., Circulation, 1997, 96, p.2520-2525).

  Until now, several compounds having a DGAT inhibitory action are known, but all have structures different from the compounds of the present invention (see, for example, Patent Document 1 or Non-Patent Documents 1 to 4).

In addition, compounds having a structure similar to the compound of the present invention are known, but it is not known that they exhibit a DGAT inhibitory action (see, for example, Patent Document 2).
JP 2002-306199 A International Publication No. 02/38554 pamphlet Tomoda, H. et al., J. Antibiot. (Tokyo), 1995, Vol. 48, p.937-941 Yang, DJ et al., J. Antibiot. (Tokyo), 1996, 49, p.223-229 Tomoda, H. et al., J. Antibiot. (Tokyo), 1999, Vol. 52, p.689-694 Tabata, N. et al., Phytochemistry, 1997, 46, p.683-687

As a result of diligent research on a compound having a DGAT inhibitory effect, the inventors have found that a sulfonamide compound having a specific chemical structure has an excellent DGAT inhibitory action, such as obesity, obesity, hyperlipidemia, high TGemia, dyslipidemia, insulin resistance syndrome, impaired glucose tolerance, diabetes, diabetic complications (including diabetic peripheral neuropathy, diabetic nephropathy, diabetic retinopathy, diabetic macroangiopathy), High fat resulting from cataract, gestational diabetes, polycystic ovary syndrome, arteriosclerosis (including arteriosclerosis caused by the diseases shown above and below), atherosclerosis, diabetic arteriosclerosis, or obesity , HyperTG, dyslipidemia, insulin resistance syndrome, impaired glucose tolerance, diabetes, diabetic complications (diabetic peripheral neuropathy, diabetic nephropathy, diabetic retinopathy, diabetic macroangiopathy, etc. Including ), Cataract, gestational diabetes mellitus, polycystic ovary syndrome, arteriosclerosis (including arteriosclerosis caused by the diseases shown above and below), atherosclerosis, diabetic arteriosclerosis, hypertension, cerebrovascular disorder The present invention was completed by finding it useful as a therapeutic or prophylactic agent for coronary artery disease, fatty liver, respiratory abnormalities, low back pain, knee osteoarthritis, gout, or cholelithiasis.

The sulfonamide compound, which is an active ingredient of the acyl coenzyme A: diacylglycerol acyltransferase inhibitor of the present invention,
(1) General formula (I)

[Wherein, A ¹ is an optionally substituted C ₁ -C ₈ alkyl group (the substituents are the same or different and each represent 1 to 3 groups selected from substituent group α),
An optionally substituted phenyl- (C ₁ -C ₆ alkyl) group (the substituents are the same or different and represent 1 to 3 groups selected from substituent group α);
An optionally substituted phenoxy- (C ₁ -C ₆ alkyl) group (the substituents may be the same or different and each represent 1 to 3 groups selected from substituent group α);
An optionally substituted phenoxyphenyl- (C ₁ -C ₆ alkyl) group (the substituents are the same or different and each represent 1 to 3 groups selected from substituent group α);
A C ₃ -C ₈ cycloalkyl group which may be substituted (the substituents are the same or different and represent 1 to 3 groups selected from the substituent group α),
A phenyl group which may be substituted (the substituents are the same or different and represent 1 to 3 groups selected from substituent group α);
A substituted phenyl group [the substituent is an essential phenyl group which may be substituted (the substituents are the same or different and represent 1 to 3 groups selected from the substituent group α)] And optionally represents the same or different and 1 to 2 groups selected from the substituent group α],
A substituted phenyl group [the substituent is, as essential, a 4- to 8-membered group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom, which may be substituted] A heterocyclyl group (the substituents are the same or different and represent 1 to 3 groups selected from the substituent group α), and are optionally the same or different and selected from the substituent group α; To 2 groups]
An optionally substituted phenoxyphenyl group (the substituents are the same or different and represent 1 to 3 groups selected from substituent group α),
A benzoylphenyl group which may be substituted (the substituents are the same or different and represent 1 to 3 groups selected from substituent group α);
A naphthyl group which may be substituted (the substituents are the same or different and represent 1 to 3 groups selected from substituent group α),
An indanyl, indenyl, tetrahydronaphthyl, or dihydronaphthyl group which may be substituted (the substituents are the same or different and represent 1 to 3 groups selected from the substituent group α);
A 4- to 8-membered heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom, which may be substituted (the substituents may be the same or different, and the substituent group α 1 to 3 groups selected from
A substituted 5- to 6-membered aromatic heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom [the substituent is substituted as an essential one; Or a phenyl group (the substituents are the same or different and represent 1 to 3 groups selected from the substituent group α), and are optionally the same or different and selected from the substituent group α. 1 to 2 groups]
A substituted 5- to 6-membered aromatic heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom [the substituent is substituted as an essential one; A 4- to 8-membered heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom (the substituents may be the same or different and selected from the substituent group α) And optionally represents the same or different and 1 to 2 groups selected from the substituent group α], or
An optionally substituted 8- to 10-membered aromatic heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom (the substituents may be the same or different, 1 to 3 groups selected from group α)
A ² is an optionally substituted C ₁ -C ₈ alkyl group (the substituents are the same or different and each represent 1 to 3 groups selected from the substituent group β);
Di (C ₁ -C ₆ alkyl) amino- (C ₁ -C ₆ alkyl) group which may be substituted (the substituent is the same or different and represents 1 to 3 groups selected from substituent group β) Show),
(C ₁ -C ₆ alkylthio)-(C ₁ -C ₆ alkyl) group which may be substituted (the substituent is the same or different and represents 1 to 3 groups selected from substituent group β) ,
An optionally substituted phenyl- (C ₁ -C ₆ alkyl) group (the substituents are the same or different and represent 1 to 3 groups selected from substituent group β),
An optionally substituted (4- to 8-membered heterocyclyl containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom)-(C ₁ -C ₆ alkyl) group (the substituent Are the same or different and represent 1 to 3 groups selected from the substituent group β),
An optionally substituted phenoxy- (C ₁ -C ₆ alkyl) group (the substituents are the same or different and represent 1 to 3 groups selected from substituent group β),
A C ₃ -C ₈ cycloalkyl group which may be substituted (the substituents are the same or different and represent 1 to 3 groups selected from substituent group β),
A phenyl group which may be substituted (the substituents are the same or different and represent 1 to 3 groups selected from the substituent group β);
A substituted phenyl group [the substituent is an optionally substituted phenyl group (the substituent is the same or different and represents 1 to 3 groups selected from the substituent group β)] And optionally represents the same or different and 1 to 2 groups selected from the substituent group β],
A substituted phenyl group [the substituent is, as essential, a 4- to 8-membered group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom, which may be substituted] 1 represents a heterocyclyl group (the substituents are the same or different and represent 1 to 3 groups selected from the substituent group β), and are optionally the same or different and selected from the substituent group β. To 2 groups]
An optionally substituted naphthyl group (the substituents are the same or different and represent 1 to 3 groups selected from substituent group β),
Optionally substituted indanyl, indenyl, tetrahydronaphthyl, or dihydronaphthyl group (the substituents are the same or different and represent 1 to 3 groups selected from substituent group β),
Optionally substituted 5- to 6-membered aromatic heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom (the substituents may be the same or different, 1 to 3 groups selected from group β)
A substituted 5- to 6-membered aromatic heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom [the substituent is substituted as an essential one; Or a phenyl group (the substituents are the same or different and represent 1 to 3 groups selected from the substituent group β), and are optionally the same or different and selected from the substituent group β. 1 to 2 groups]
A substituted 5- to 6-membered aromatic heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom [the substituent is substituted as an essential one; A 4- to 8-membered heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom (the substituents are the same or different and are selected from the substituent group β) And optionally represents the same or different and 1 to 2 groups selected from the substituent group β], or
An optionally substituted 8- to 10-membered aromatic heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom (the substituents may be the same or different, Represents 1 to 3 groups selected from group β);
A ³ is an optionally substituted phenyl- (C ₁ -C ₆ alkyl) group (the substituents are the same or different and each represent 1 to 3 groups selected from substituent group β);
An optionally substituted naphthylmethyl group (the substituents are the same or different and represent 1 to 3 groups selected from substituent group β),
A phenyl group which may be substituted (the substituents are the same or different and represent 1 to 3 groups selected from the substituent group β);
A substituted phenyl group [the substituent is an optionally substituted phenyl group (the substituent is the same or different and represents 1 to 3 groups selected from the substituent group β)] And optionally represents the same or different and 1 to 2 groups selected from the substituent group β],
A substituted phenyl group [the substituent is, as essential, a 4- to 8-membered group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom, which may be substituted] 1 represents a heterocyclyl group (the substituents are the same or different and represent 1 to 3 groups selected from the substituent group β), and are optionally the same or different and selected from the substituent group β. To 2 groups]
An optionally substituted naphthyl group (the substituents are the same or different and represent 1 to 3 groups selected from substituent group β),
Optionally substituted 5- to 6-membered aromatic heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom (the substituents may be the same or different, 1 to 3 groups selected from group β)
A substituted 5- to 6-membered aromatic heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom [the substituent is substituted as an essential one; Or a phenyl group (the substituents are the same or different and represent 1 to 3 groups selected from the substituent group β), and are optionally the same or different and selected from the substituent group β. 1 to 2 groups]
A substituted 5- to 6-membered aromatic heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom [the substituent is substituted as an essential one; A 4- to 8-membered heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom (the substituents are the same or different and are selected from the substituent group β) And optionally represents the same or different and 1 to 2 groups selected from the substituent group β], or
An optionally substituted 8- to 10-membered aromatic heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom (the substituents may be the same or different, Represents 1 to 3 groups selected from group β);
R ¹ represents a group having the formula —NHCO—, —NR ^1b CO— (R ^1b represents a C ₁ -C ₆ alkyl group) or —CO—;
R ² represents a hydrogen atom or a C ₁ -C ₆ alkyl group;
Substituent group α is C ₁ -C ₆ alkyl, halogeno C ₁ -C ₆ alkyl, hydroxy C ₁ -C ₆ alkyl, aminosulfonyl C ₁ -C ₆ alkyl, (C ₁ -C ₆ alkyl) aminosulfonyl- ( C ₁ -C ₆ alkyl), hydroxyimino C ₁ -C ₆ alkyl, (C ₁ -C ₆ alkoxyimino) - (C ₁ -C ₆ alkyl), C ₃ -C ₈ cycloalkyl, C ₂ -C ₆ alkynyl , hydroxy, C ₁ -C ₆ alkoxy, halogeno C ₁ -C ₆ alkoxy, formyloxy, C ₂ -C ₇ alkylcarbonyloxy, C ₁ -C ₆ alkylthio, C ₁ -C ₆ alkylsulfinyl, C ₁ -C ₆ alkylsulfonyl, aminosulfonyl, (C ₁ -C ₆ alkyl) aminosulfonyl, amino, C ₁ -C ₆ alkylamino, di (C ₁ -C ₆ alkyl) amino (said alkyl groups may be the same or different ), Formylamino, C ₂ -C ₇ alkylcarbonylamino, C ₂ -C ₇ alkoxycarbonylamino, C ₁ -C ₆ alkylsulfonylamino, formyl, C ₂ -C ₇ alkylcarbonyl, carboxy, C ₂ -C ₇ alkoxy carbonyl, carbamoyl, C ₂ -C ₇ alkylaminocarbonyl, di (C ₁ -C ₆ alkyl) aminocarbonyl (the alkyl group, the same or different), a group having a cyano, nitro, halogeno, equation -OCH ₂ COR ³ [Wherein R ³ represents hydroxy, C ₁ -C ₆ alkoxy, amino, C ₁ -C ₆ alkylamino, or di (C ₁ -C ₆ alkyl) amino (the alkyl groups are the same or different). A group having the formula —CH ₂ COOR ⁴ , wherein R ⁴ represents a hydrogen atom or C ₁ -C ₆ alkyl, and a C ₁ -C ₄ alkyl Indicates a group consisting of a rangeoxy group;
Substituent group β is C ₁ -C ₆ alkyl, halogeno C ₁ -C ₆ alkyl, C ₃ -C ₈ cycloalkyl, hydroxy, C ₁ -C ₆ alkoxy, halogeno C ₁ -C ₆ alkoxy, formyloxy, C ₂ -C ₇ alkylcarbonyloxy, C ₁ -C ₆ alkylthio, C ₁ -C ₆ alkylsulfinyl, C ₁ -C ₆ alkylsulfonyl, amino, C ₁ -C ₆ alkylamino, di (C ₁ -C ₆ alkyl) amino (said alkyl groups may be the same or different), formylamino, C ₂ -C ₇ alkylcarbonylamino, C ₂ -C ₇ alkoxycarbonylamino, formyl, C ₂ -C ₇ alkylcarbonyl, carboxy, C ₂ -C ₇ Alkoxycarbonyl, carbamoyl, C ₂ -C ₇ alkylaminocarbonyl, di (C ₁ -C ₆ alkyl) aminocarbonyl (the alkyl groups are the same Or cyano, nitro, halogeno, a group having the formula —CH ₂ COOR ⁴ (wherein R ⁴ represents a hydrogen atom or C ₁ -C ₆ alkyl), and C ₁ -C ₄ alkylenedi A group consisting of an oxy group is shown. ].

In the sulfonamide compound having the general formula (I),
(2) General formula (Ia)

[ ^Wherein , A ^1a represents an optionally substituted phenyl group (the substituents are the same or different and represent 1 to 3 groups selected from substituent group α),
A substituted phenyl group [the substituent is an essential phenyl group which may be substituted (the substituents are the same or different and represent 1 to 3 groups selected from the substituent group α)] And optionally represents the same or different and 1 to 2 groups selected from the substituent group α],
A substituted phenyl group [the substituent is, as essential, a 4- to 8-membered group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom, which may be substituted] A heterocyclyl group (the substituents are the same or different and represent 1 to 3 groups selected from the substituent group α), and are optionally the same or different and selected from the substituent group α; To 2 groups]
A 5- to 6-membered aromatic heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom, which may be substituted (the substituents may be the same or different, 1 to 3 groups selected from group α)
A substituted 5- to 6-membered aromatic heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom [the substituent is substituted as essential Or a phenyl group (the substituents are the same or different and represent 1 to 3 groups selected from the substituent group α), and are optionally the same or different and selected from the substituent group α. 1 or 2 groups], or
A substituted 5- to 6-membered aromatic heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom [the substituent is substituted as essential A 4- to 8-membered heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom (the substituents may be the same or different and selected from the substituent group α) And optionally represents the same or different and 1 to 2 groups selected from the substituent group α];
A ^2a represents a phenyl group which may be substituted (the substituents are the same or different and each represent 1 to 3 groups selected from the substituent group β);
A substituted phenyl group [the substituent is an optionally substituted phenyl group (the substituent is the same or different and represents 1 to 3 groups selected from the substituent group β)] And optionally represents the same or different and 1 to 2 groups selected from the substituent group β],
A substituted phenyl group [the substituent is, as essential, a 4- to 8-membered heterocyclyl having 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom] A group (the substituents are the same or different and represent 1 to 3 groups selected from the substituent group β), and optionally are the same or different and are selected from the substituent group β 2 groups are shown]
An optionally substituted naphthyl group (the substituents are the same or different and represent 1 to 3 groups selected from substituent group β),
Optionally substituted 5- to 6-membered aromatic heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom (the substituents may be the same or different, 1 to 3 groups selected from group β)
A substituted 5- to 6-membered aromatic heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom [the substituent is substituted as an essential one; Or a phenyl group (the substituents are the same or different and represent 1 to 3 groups selected from the substituent group β), and are optionally the same or different and selected from the substituent group β. 1 to 2 groups]
A substituted 5- to 6-membered aromatic heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom [the substituent is substituted as an essential one; A 4- to 8-membered heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom (the substituents are the same or different and are selected from the substituent group β) And optionally represents the same or different and 1 to 2 groups selected from the substituent group β], or
An optionally substituted 8- to 10-membered aromatic heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom (the substituents may be the same or different, Represents 1 to 3 groups selected from group β);
A ^3a represents a substituted phenyl group [the substituent is an essential phenyl group which may be substituted (the substituents may be the same or different and each may have 1 to 3 substituents selected from the substituent group β]; And optionally represents one or two groups selected from the same or different, substituent group β],
A substituted phenyl group [the substituent is, as essential, a 4- to 8-membered group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom, which may be substituted] 1 represents a heterocyclyl group (the substituents are the same or different and represent 1 to 3 groups selected from the substituent group β), and are optionally the same or different and selected from the substituent group β. To 2 groups]
An optionally substituted naphthyl group (the substituents are the same or different and represent 1 to 3 groups selected from substituent group β),
A substituted 5- to 6-membered aromatic heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom [the substituent is substituted as an essential one; Or a phenyl group (the substituents are the same or different and represent 1 to 3 groups selected from the substituent group β), and are optionally the same or different and selected from the substituent group β. 1 to 2 groups]
A substituted 5- to 6-membered aromatic heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom [the substituent is substituted as an essential one; A 4- to 8-membered heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom (the substituents are the same or different and are selected from the substituent group β) And optionally represents the same or different and 1 to 2 groups selected from the substituent group β], or
An optionally substituted 8- to 10-membered aromatic heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom (the substituents may be the same or different, Represents 1 to 3 groups selected from group β);
R ^1a represents a group having the formula —NHCO— or —CO—;
Substituent group α is C ₁ -C ₆ alkyl, halogeno C ₁ -C ₆ alkyl, hydroxy C ₁ -C ₆ alkyl, aminosulfonyl C ₁ -C ₆ alkyl, (C ₁ -C ₆ alkyl) aminosulfonyl- ( C ₁ -C ₆ alkyl), hydroxyimino C ₁ -C ₆ alkyl, (C ₁ -C ₆ alkoxyimino) - (C ₁ -C ₆ alkyl), C ₃ -C ₈ cycloalkyl, C ₂ -C ₆ alkynyl , hydroxy, C ₁ -C ₆ alkoxy, halogeno C ₁ -C ₆ alkoxy, formyloxy, C ₂ -C ₇ alkylcarbonyloxy, C ₁ -C ₆ alkylthio, C ₁ -C ₆ alkylsulfinyl, C ₁ -C ₆ alkylsulfonyl, aminosulfonyl, (C ₁ -C ₆ alkyl) aminosulfonyl, amino, C ₁ -C ₆ alkylamino, di (C ₁ -C ₆ alkyl) amino (said alkyl groups may be the same or different ), Formylamino, C ₂ -C ₇ alkylcarbonylamino, C ₂ -C ₇ alkoxycarbonylamino, C ₁ -C ₆ alkylsulfonylamino, formyl, C ₂ -C ₇ alkylcarbonyl, carboxy, C ₂ -C ₇ alkoxy carbonyl, carbamoyl, C ₂ -C ₇ alkylaminocarbonyl, di (C ₁ -C ₆ alkyl) aminocarbonyl (the alkyl group, the same or different), a group having a cyano, nitro, halogeno, equation -OCH ₂ COR ³ [Wherein R ³ represents hydroxy, C ₁ -C ₆ alkoxy, amino, C ₁ -C ₆ alkylamino, or di (C ₁ -C ₆ alkyl) amino (the alkyl groups are the same or different). A group having the formula —CH ₂ COOR ⁴ , wherein R ⁴ represents a hydrogen atom or C ₁ -C ₆ alkyl, and a C ₁ -C ₄ alkyl Indicates a group consisting of a rangeoxy group;
Substituent group β is C ₁ -C ₆ alkyl, halogeno C ₁ -C ₆ alkyl, C ₃ -C ₈ cycloalkyl, hydroxy, C ₁ -C ₆ alkoxy, halogeno C ₁ -C ₆ alkoxy, formyloxy, C ₂ -C ₇ alkylcarbonyloxy, C ₁ -C ₆ alkylthio, C ₁ -C ₆ alkylsulfinyl, C ₁ -C ₆ alkylsulfonyl, amino, C ₁ -C ₆ alkylamino, di (C ₁ -C ₆ alkyl) amino (said alkyl groups may be the same or different), formylamino, C ₂ -C ₇ alkylcarbonylamino, C ₂ -C ₇ alkoxycarbonylamino, formyl, C ₂ -C ₇ alkylcarbonyl, carboxy, C ₂ -C ₇ Alkoxycarbonyl, carbamoyl, C ₂ -C ₇ alkylaminocarbonyl, di (C ₁ -C ₆ alkyl) aminocarbonyl (the alkyl groups are the same Or cyano, nitro, halogeno, a group having the formula —CH ₂ COOR ⁴ (wherein R ⁴ represents a hydrogen atom or C ₁ -C ₆ alkyl), and C ₁ -C ₄ alkylenedi A group consisting of an oxy group is shown. However, the case where A ^1a is a 4- (thiazol-4-yl) phenyl group which may be substituted is excluded. ] Is a novel compound.

Among the sulfonamide compounds having the general formula (Ia), suitable compounds are:
(3) A ^1a may be substituted phenyl group (the substituents are the same or different and represent 1 to 3 groups selected from substituent group α),
A substituted phenyl group [the substituent is, as essential, a 4- to 8-membered group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom, which may be substituted] A heterocyclyl group (the substituents are the same or different and represent 1 to 3 groups selected from the substituent group α), and are optionally the same or different and selected from the substituent group α; To 2 groups]
Optionally substituted 5- to 6-membered aromatic heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom (the substituents may be the same or different, 1 to 3 groups selected from group α), or
A substituted 5- to 6-membered aromatic heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom [the substituent is substituted as an essential one; A 4- to 8-membered heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom (the substituents may be the same or different and selected from the substituent group α) 1 to 3 groups), and optionally represents the same or different and 1 to 2 groups selected from the substituent group α]
(4) A ^1a may be substituted phenyl, thiazolyl, isothiazolyl, or pyridyl group (the substituents are the same or different and represent 1 to 2 groups selected from the substituent group α1) Or a substituted phenyl, thiazolyl, isothiazolyl or pyridyl group [the substituent is, as an essential one, selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom which may be substituted 1 A 5- to 7-membered heterocyclyl group containing 1 to 4 atoms (the substituents are the same or different and represent 1 to 2 groups selected from the substituent group α1), optionally substituted Shows one group selected from the base group α1],
Substituent group α1 is C ₁ -C ₄ alkyl, halogeno C ₁ -C ₄ alkyl, hydroxy C ₁ -C ₄ alkyl, hydroxyimino C ₁ -C ₄ alkyl, (C ₁ -C ₄ alkoxyimino)-(C ₁ -C ₄ alkyl), C ₃ -C ₆ cycloalkyl, C ₂ -C ₄ alkynyl, C ₁ -C ₄ alkoxy, halogeno C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ alkyl sulfinyl, C ₁ -C ₄ alkylsulfonyl, C ₁ -C ₄ alkylamino, di (C ₁ -C ₄ alkyl) amino (said alkyl groups may be the same or different), formyl, C ₂ -C ₅ alkylcarbonyl, C ₂ -C ₅ alkoxycarbonyl, carbamoyl, C ₂ -C ₅ alkylaminocarbonyl, di (C ₁ -C ₄ alkyl) aminocarbonyl (the alkyl group, the same or different), cyano, nitro Fluoro, chloro, bromo, group [wherein having the formula -OCH ₂ COR ^3a, R ^3a is, C ₁ -C ₄ alkoxy, amino, C ₁ -C ₄ alkylamino, di (C ₁ -C ₄ alkyl) amino (The alkyl groups are the same or different), or a group having the formula —CH ₂ COOR ^4a (wherein R ^4a represents C ₁ -C ₄ alkyl) and C ₁ -C ₃ alkylenedioxy A compound which is a group consisting of groups,
(5) A ^1a is a substituted phenyl group [the substituent is, as essential, 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom, which may be substituted] A 5- to 6-membered aromatic heterocyclyl group containing 1 to 2 (the substituents are the same or different and each represents 1 to 2 groups selected from the substituent group α2), and the optional substituent group α2 Represents one group selected from]
Substituent group α2 is C ₁ -C ₄ alkyl, halogeno C ₁ -C ₄ alkyl, hydroxymethyl, hydroxyethyl, hydroxyiminomethyl, hydroxyiminoethyl, methoxyiminomethyl, ethoxyiminomethyl, methoxyiminoethyl, ethoxyiminoethyl. , Ethynyl, propynyl, C ₁ -C ₄ alkoxy, halogeno C ₁ -C ₄ alkoxy, methylthio, ethylthio, C ₁ -C ₄ alkylamino, di (C ₁ -C ₄ alkyl) amino (the alkyl groups are the same or Different), formyl, C ₂ -C ₅ alkylcarbonyl, methoxycarbonyl, ethoxycarbonyl, carbamoyl, methylaminocarbonyl, ethylaminocarbonyl, di (C ₁ -C ₄ alkyl) aminocarbonyl (the alkyl groups are the same or different) , Cyano, nitro, fluoro, Chloro, bromo, a group having the formula —OCH ₂ COR ^3b [wherein R ^3b is methoxy, ethoxy, amino, C ₁ -C ₄ alkylamino, or di (C ₁ -C ₄ alkyl) amino (the alkyl The groups are the same or different)], a group having the formula —CH ₂ COOR ^4b (R ^4b represents methyl or ethyl), and a compound consisting of a C ₁ -C ₃ alkylenedioxy group,
(6) A ^1a is a substituted phenyl group [this substituent is optionally substituted pyrrolyl, pyrazolyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, triazolyl, or , A tetrazolyl group (the substituents are the same or different and represent 1 to 2 groups selected from the substituent group α3), and optionally, one group selected from the substituent group α3 Indicating]
Substituent group α3 is methyl, ethyl, fluoromethyl, chloromethyl, difluoromethyl, trifluoromethyl, pentafluoroethyl, fluoromethoxy, chloromethoxy, difluoromethoxy, trifluoromethoxy, pentafluoroethoxy, methoxy, ethoxy, methylamino , Ethylamino, dimethylamino, diethylamino, methylcarbonyl, ethylcarbonyl, dimethylaminocarbonyl, diethylaminocarbonyl, cyano, nitro, fluoro, chloro, and a group having the formula —OCH ₂ COR ^3c where R ^3c is amino , Methylamino, ethylamino, dimethylamino, or diethylamino), a compound that is a group consisting of methylenedioxy and ethylenedioxy groups,
(7) A ^2a is an optionally substituted phenyl group (the substituents are the same or different and represent 1 to 3 groups selected from substituent group β),
An optionally substituted naphthyl group (the substituents are the same or different and represent 1 to 3 groups selected from substituent group β),
Optionally substituted 5- to 6-membered aromatic heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom (the substituents may be the same or different, 1 to 3 groups selected from group β), or
An optionally substituted 8- to 10-membered aromatic heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom (the substituents may be the same or different, A compound according to any one of (2) to (6), which represents 1 to 3 groups selected from group β);
(8) A ^2a is a phenyl group which may be substituted (the substituents are the same or different and represent 1 to 2 groups selected from the substituent group β1), or
A 5- to 6-membered aromatic heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom which may be substituted (the heterocyclyl group is one or more nitrogen atoms) And may contain an oxygen atom and a sulfur atom, and the substituents are the same or different and represent 1 to 2 groups selected from the substituent group β1),
Substituent group β1 is C ₁ -C ₄ alkyl, halogeno C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, halogeno C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ alkylsulfinyl. C ₁ -C ₄ alkylsulfonyl, amino, C ₁ -C ₄ alkylamino, di (C ₁ -C ₄ alkyl) amino (the alkyl groups are the same or different), formyl, C ₂ -C ₅ alkylcarbonyl, C ₂ -C ₅ alkoxycarbonyl, carbamoyl, C ₂ -C ₅ aminocarbonyl, di (C ₁ -C ₄ alkyl) aminocarbonyl (the alkyl groups are the same or different), cyano, nitro, fluoro, chloro, bromo, And a compound described in any one of (2) to (6), which is a group consisting of a C ₁ -C ₃ alkylenedioxy group,
(9) A ^2a is an optionally substituted phenyl or pyridyl group (the substituents are the same or different and represent 1 to 2 groups selected from the substituent group β2);
Substituent group β2 is C ₁ -C ₄ alkyl, halogeno C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, fluoromethoxy, chloromethoxy, difluoromethoxy, trifluoromethoxy, pentafluoroethoxy, methylthio, ethylthio, methyl Sulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, methylamino, ethylamino, dimethylamino, diethylamino, formyl, methylcarbonyl, ethylcarbonyl, methoxycarbonyl, ethoxycarbonyl, carbamoyl, methylaminocarbonyl, ethylaminocarbonyl, dimethylaminocarbonyl, (2) to (6), which are a group consisting of diethylaminocarbonyl, cyano, nitro, fluoro, chloro, bromo, methylenedioxy, and ethylenedioxy groups Compounds described in or Re,
(10) A ^2a is a phenyl group which may be substituted (the substituents are the same or different and represent 1 to 2 groups selected from the substituent group β3);
Substituent group β3 is a group consisting of methyl, ethyl, fluoromethyl, chloromethyl, difluoromethyl, trifluoromethyl, pentafluoroethyl, methoxy, ethoxy, fluoro, and chloro groups of (2) to (6) A compound described in any of the above,
(11) A ^3a may be substituted (the substituents are the same or different and represent 1 to 3 groups selected from substituent group β), or may be substituted; 8- to 10-membered aromatic heterocyclyl group containing 1 to 4 atoms selected from the group consisting of nitrogen atom, oxygen atom and sulfur atom (the substituents are the same or different and are selected from substituent group β) The compound according to any one of (2) to (10), which represents 1 to 3 groups);
(12) A ^3a may be substituted (the substituents are the same or different and represent 1 to 2 groups selected from substituent group β1), or may be substituted; A 9 to 10-membered aromatic heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom (the heterocyclyl group contains one or more nitrogen atoms, an oxygen atom Or a sulfur atom, and the substituents are the same or different and represent one or two groups selected from the substituent group β1). (2) to (10) Compound,
(13) A ^3a is an optionally substituted naphthyl, quinolyl, isoquinolyl, quinazolinyl, or quinoxalinyl group (the substituents are the same or different and each represents one or two groups selected from substituent group β4) And
Substituent group β4 is C ₁ -C ₄ alkyl, halogeno C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, fluoromethoxy, chloromethoxy, difluoromethoxy, trifluoromethoxy, pentafluoroethoxy, methylthio, ethylthio, methyl sulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, amino, C ₁ -C ₄ alkylamino, di (C ₁ -C ₄ alkyl) amino (said alkyl groups may be the same or different), formyl, methylcarbonyl, ethylcarbonyl, Methoxycarbonyl, ethoxycarbonyl, carbamoyl, methylaminocarbonyl, ethylaminocarbonyl, dimethylaminocarbonyl, diethylaminocarbonyl, cyano, nitro, fluoro, chloro, bromo, methylenedioxy, and ethylene dioxide Compounds described in any one of a group consisting of groups (2) to (10),
(14) A ^3a is an optionally substituted naphthyl or quinolyl group (the substituents are the same or different and represent 1 to 2 groups selected from the substituent group β5);
Substituent group β5 consists of methyl, ethyl, fluoromethyl, chloromethyl, difluoromethyl, trifluoromethyl, pentafluoroethyl, methoxy, ethoxy, methylamino, ethylamino, dimethylamino, diethylamino, fluoro, and chloro groups A compound described in any one of (2) to (10) which is a group, or
(15) The compound described in any one of (2) to (14), wherein R ^1a is a group having the formula —NHCO—.

A ^1a selected from (3) to (6) above, A ^2a selected from (7) to (10), A ^3a selected from (11) to (14), and (15) selected A compound obtained by arbitrarily combining R ^1a thus obtained is more preferable.

In the sulfonamide compound having the general formula (Ia), more preferable compounds are, for example,
(16) A ^1a is a phenyl group which may be substituted (the substituents are the same or different and represent 1 to 3 groups selected from the substituent group α);
A substituted phenyl group [the substituent is an essential phenyl group which may be substituted (the substituents are the same or different and represent 1 to 3 groups selected from the substituent group α)] And optionally represents the same or different and 1 to 2 groups selected from the substituent group α],
A substituted phenyl group [the substituent is, as essential, a 4- to 8-membered group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom, which may be substituted] A heterocyclyl group (the substituents are the same or different and represent 1 to 3 groups selected from the substituent group α), and are optionally the same or different and selected from the substituent group α; To 2 groups]
A 5- to 6-membered aromatic heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom, which may be substituted (the substituents may be the same or different, 1 to 3 groups selected from group α)
A substituted 5- to 6-membered aromatic heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom [the substituent is substituted as essential Or a phenyl group (the substituents are the same or different and represent 1 to 3 groups selected from the substituent group α), and are optionally the same or different and selected from the substituent group α. 1 or 2 groups], or
A substituted 5- to 6-membered aromatic heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom [the substituent is substituted as an essential one; A 4- to 8-membered heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom (the substituents may be the same or different and selected from the substituent group α) And optionally represents the same or different and 1 to 2 groups selected from the substituent group α];
A ^2a is a phenyl group which may be substituted (the substituents are the same or different and each represent 1 to 3 groups selected from substituent group β);
A substituted phenyl group [the substituent is an optionally substituted phenyl group (the substituent is the same or different and represents 1 to 3 groups selected from the substituent group β)] And optionally represents the same or different and 1 to 2 groups selected from the substituent group β],
A substituted phenyl group [the substituent is, as essential, a 4- to 8-membered heterocyclyl having 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom] A group (the substituents are the same or different and represent 1 to 3 groups selected from the substituent group β), and optionally are the same or different and are selected from the substituent group β 2 groups are shown]
An optionally substituted naphthyl group (the substituents are the same or different and represent 1 to 3 groups selected from substituent group β),
Optionally substituted 5- to 6-membered aromatic heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom (the substituents may be the same or different, 1 to 3 groups selected from group β)
A substituted 5- to 6-membered aromatic heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom [the substituent is substituted as an essential one; Or a phenyl group (the substituents are the same or different and represent 1 to 3 groups selected from the substituent group β), and are optionally the same or different and selected from the substituent group β. 1 to 2 groups]
A substituted 5- to 6-membered aromatic heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom [the substituent is substituted as an essential one; A 4- to 8-membered heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom (the substituents are the same or different and are selected from the substituent group β) And optionally represents the same or different and 1 to 2 groups selected from the substituent group β], or
An optionally substituted 8- to 10-membered aromatic heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom (the substituents may be the same or different, 1 to 3 groups selected from group β)
A ^3a is a substituted phenyl group [the substituent is an essential phenyl group which may be substituted (the substituents may be the same or different, and 1 to 3 substituents selected from the substituent group β] And optionally represents the same or different one or two groups selected from the substituent group β],
A substituted phenyl group [the substituent is, as essential, a 4- to 8-membered group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom, which may be substituted] 1 represents a heterocyclyl group (the substituents are the same or different and represent 1 to 3 groups selected from the substituent group β), and are optionally the same or different and selected from the substituent group β. To 2 groups]
An optionally substituted naphthyl group (the substituents are the same or different and represent 1 to 3 groups selected from substituent group β),
A substituted 5- to 6-membered aromatic heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom [the substituent is substituted as an essential one; Or a phenyl group (the substituents are the same or different and represent 1 to 3 groups selected from the substituent group β), and are optionally the same or different and selected from the substituent group β. 1 to 2 groups]
A substituted 5- to 6-membered aromatic heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom [the substituent is substituted as an essential one; A 4- to 8-membered heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom (the substituents are the same or different and are selected from the substituent group β) And optionally represents the same or different and 1 to 2 groups selected from the substituent group β], or
An optionally substituted 8- to 10-membered aromatic heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom (the substituents may be the same or different, 1 to 3 groups selected from group β)
A compound wherein R ^1a is a group having the formula —NHCO—;
(17) A ^1a is a phenyl group which may be substituted (the substituents are the same or different and represent 1 to 3 groups selected from the substituent group α);
A substituted phenyl group [the substituent is, as essential, a 4- to 8-membered group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom, which may be substituted] A heterocyclyl group (the substituents are the same or different and represent 1 to 3 groups selected from the substituent group α), and are optionally the same or different and selected from the substituent group α; To 2 groups]
Optionally substituted 5- to 6-membered aromatic heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom (the substituents may be the same or different, 1 to 3 groups selected from group α), or
A substituted 5- to 6-membered aromatic heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom [the substituent is substituted as an essential one; A 4- to 8-membered heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom (the substituents may be the same or different and selected from the substituent group α) 1 to 3 groups, and optionally, the same or different and 1 to 2 groups selected from the substituent group α are represented]
A ^2a is a phenyl group which may be substituted (the substituents are the same or different and each represent 1 to 3 groups selected from substituent group β);
An optionally substituted naphthyl group (the substituents are the same or different and represent 1 to 3 groups selected from substituent group β),
Optionally substituted 5- to 6-membered aromatic heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom (the substituents may be the same or different, 1 to 3 groups selected from group β), or
An optionally substituted 8- to 10-membered aromatic heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom (the substituents may be the same or different, 1 to 3 groups selected from group β)
A ^3a is a naphthyl group which may be substituted (the substituents are the same or different and each represent 1 to 3 groups selected from substituent group β), or a nitrogen atom which may be substituted, An 8- to 10-membered aromatic heterocyclyl group containing 1 to 4 atoms selected from the group consisting of an oxygen atom and a sulfur atom (the substituents are the same or different and are selected from 1 to 3 selected from the substituent group β) Number of groups)
A compound wherein R ^1a is a group having the formula —NHCO—;
(18) A ^1a may be substituted phenyl, thiazolyl, isothiazolyl, or pyridyl group (the substituents are the same or different and represent 1 to 2 groups selected from the substituent group α1) Or a substituted phenyl, thiazolyl, isothiazolyl or pyridyl group [the substituent is, as an essential one, selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom which may be substituted 1 A 5- to 7-membered heterocyclyl group containing 1 to 4 atoms (the substituents are the same or different and represent 1 to 2 groups selected from the substituent group α1), optionally substituted Shows one group selected from the base group α1],
A ^2a is a phenyl group which may be substituted (the substituents are the same or different and each represents 1 to 2 groups selected from the substituent group β1), or
A 5- to 6-membered aromatic heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom which may be substituted (the heterocyclyl group is one or more nitrogen atoms) And may contain an oxygen atom and a sulfur atom, and the substituents are the same or different and represent 1 to 2 groups selected from the substituent group β1),
A ^3a is an optionally substituted naphthyl group (the substituents are the same or different and represent 1 to 2 groups selected from the substituent group β1), or a nitrogen atom, which may be substituted, 9 to 10-membered aromatic heterocyclyl group containing 1 to 4 atoms selected from the group consisting of oxygen atom and sulfur atom (the heterocyclyl group contains one or more nitrogen atoms, oxygen atom and sulfur atom And the substituents are the same or different and represent 1 to 2 groups selected from the substituent group β1),
A compound wherein R ^1a is a group having the formula —NHCO—;
(19) A ^1a is a substituted phenyl group [1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom, and a sulfur atom, which are optionally substituted, as the essential group. A 5- to 6-membered aromatic heterocyclyl group containing 1 to 2 (the substituents are the same or different and each represents 1 to 2 groups selected from the substituent group α2), and the optional substituent group α2 Represents one group selected from]
A ^2a is an optionally substituted phenyl or pyridyl group (the substituents are the same or different and represent 1 to 2 groups selected from the substituent group β2);
A ^3a is an optionally substituted naphthyl, quinolyl, isoquinolyl, quinazolinyl, or quinoxalinyl group (the substituents are the same or different and each represent one or two groups selected from substituent group β4) Yes,
A compound wherein R ^1a is a group having the formula —NHCO—, or
(20) A ^1a is a substituted phenyl group [this substituent is optionally substituted, pyrrolyl, pyrazolyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, triazolyl, or , A tetrazolyl group (the substituents are the same or different and represent 1 to 2 groups selected from the substituent group α3), and optionally, one group selected from the substituent group α3 Indicating]
A ^2a is a phenyl group which may be substituted (the substituents are the same or different and represent 1 to 2 groups selected from the substituent group β3);
A ^3a is an optionally substituted naphthyl or quinolyl group (the substituents are the same or different and each represent one or two groups selected from substituent group β5);
A compound in which R ^1a is a group having the formula —NHCO—.

Furthermore, the present invention provides
(21) Acyl coenzyme A: a diacylglycerol acyltransferase inhibitor comprising as an active ingredient the compound described in any of (2) to (20) or a pharmacologically acceptable salt thereof,
(22) A pharmaceutical comprising the compound described in any of (2) to (20) or a pharmacologically acceptable salt thereof as an active ingredient,
(23) The drug is obesity, obesity, or hyperlipidemia caused by obesity, hyperTGemia, insulin resistance syndrome, impaired glucose tolerance, diabetes, diabetic complications (diabetic peripheral neuropathy, diabetic Nephropathy, diabetic retinopathy, diabetic macroangiopathy), hypertension, arteriosclerosis, cerebrovascular disorder, coronary artery disease, fatty liver, respiratory abnormalities, low back pain, knee osteoarthritis, gout, or gallstones A medicament described in (22), which is a therapeutic or preventive agent for symptom
(24) The medicine is a therapeutic or preventive agent for obesity, obesity, or hyperlipidemia, hyperTGemia, diabetes, hypertension, or arteriosclerosis caused by obesity. Drugs, or
(25) The medicament according to (22), wherein the medicament is a therapeutic or prophylactic agent for obesity or obesity.

The “C ₁ -C ₈ alkyl group” in A ¹ and A ² of the above formula (I) is a linear or branched alkyl group having 1 to 8 carbon atoms, such as a methyl group or an ethyl group 1-propyl group, 2-propyl group, 1-butyl group, 2-butyl group, 2-methyl-1-propyl group, 2-methyl-2-propyl group, 1-pentyl group, 2-pentyl group, 3 -Pentyl group, 2-methyl-2-butyl group, 3-methyl-2-butyl group, 1-hexyl group, 2-hexyl group, 3-hexyl group, 2-methyl-1-pentyl group, 3-methyl- It may be a 1-pentyl group, 2-ethyl-1-butyl group, 2,2-dimethyl-1-butyl group, 2,3-dimethyl-1-butyl group, 1-heptyl group, or 1-octyl group , preferably a C ₁ -C ₄ alkyl group, more preferably a methyl group Other is ethyl group, and most preferably a methyl group.

In formula (I) and formula (Ia),
"- (C ₁ -C ₆ alkyl) group phenyl", in (i) A ¹ "phenoxy - (C ₁ -C ₆ alkyl) group" and "phenoxyphenyl - (C ₁ -C ₆ alkyl) group" A C ₁ -C ₆ alkyl moiety of
(ii) in A ² "di (C ₁ -C ₆ alkyl) amino - (C ₁ -C ₆ alkyl) group", "(C ₁ -C ₆ alkylthio) - (C ₁ -C ₆ alkyl) group" “Phenyl- (C ₁ -C ₆ alkyl) group”, “(4- to 8-membered heterocyclyl containing 1 to 4 atoms selected from the group consisting of nitrogen atom, oxygen atom and sulfur atom) — (C ₁ -C ₆ alkyl) group "and" phenoxy - (C ₁ -C ₆ alkyl moiety of the C ₁ -C ₆ alkyl) group ";
(Iii) the C ₁ -C ₆ alkyl moiety of the “phenyl- (C ₁ -C ₆ alkyl) group” in A ³ ;
(Iv) “C ₁ -C ₆ alkyl group” in R ^1b , R ² , substituent group α and substituent group β;
(V) “(C ₁ -C ₆ alkyl) aminosulfonyl- (C ₁ -C ₆ alkyl) group” and “(C ₁ -C ₆ alkoxyimino)-(C ₁ -C ₆ alkyl)” in substituent group α C ₁ -C ₆ alkyl moiety of the group "; and,
(Vi) The “C ₁ -C ₆ alkyl group” of R ^{4 in} the group having the formula —CH ₂ COOR ⁴ in the substituent group α and the substituent group β is a straight chain or branched chain having 1 to 6 carbon atoms. A branched alkyl group, for example, methyl group, ethyl group, 1-propyl group, 2-propyl group, 1-butyl group, 2-butyl group, 2-methyl-1-propyl group, 2-methyl-2- Propyl group, 1-pentyl group, 2-pentyl group, 3-pentyl group, 2-methyl-2-butyl group, 3-methyl-2-butyl group, 1-hexyl group, 2-hexyl group, 3-hexyl group 2-methyl-1-pentyl group, 3-methyl-1-pentyl group, 2-ethyl-1-butyl group, 2,2-dimethyl-1-butyl group, or 2,3-dimethyl-1-butyl Group, preferably a C ₁ -C ₄ alkyl group, more preferably It is a methyl group or an ethyl group, and is most preferably a methyl group.

The “phenyl- (C ₁ -C ₆ alkyl) group” in A ¹ , A ² and A ³ of formula (I) is the above C ₁ -C ₆ alkyl group substituted with one phenyl group, , Phenylmethyl group, phenylethyl group (for example, 1-phenylethyl group or 2-phenylethyl group), phenylpropyl group (for example, 1-phenyl-1-propyl group, 2-phenyl-1-propyl group, 3- Phenyl-1-propyl group, 1-phenyl-2-propyl group or 2-phenyl-2-propyl group), 4-phenyl-1-butyl group, 4-phenyl-2-butyl group, 5-phenyl- It can be a 1-pentyl group, a 5-phenyl-2-pentyl group or a 6-phenyl-1-hexyl group, preferably a phenyl- (C ₁ -C ₄ alkyl) group, more preferably , Phenylmethyl group It is a phenylethyl group, and most preferably a phenylmethyl group.

The “phenoxy- (C ₁ -C ₆ alkyl) group” in A ¹ and A ² of formula (I) is the above C ₁ -C ₆ alkyl group substituted by one phenoxy group, for example, phenoxymethyl Group, phenoxyethyl group (for example, 1-phenoxyethyl group or 2-phenoxyethyl group), phenoxypropyl group (for example, 1-phenoxy-1-propyl group, 2-phenoxy-1-propyl group, 3-phenoxy-1) -Propyl group, 1-phenoxy-2-propyl group or 2-phenoxy-2-propyl group), 4-phenoxy-1-butyl group, 4-phenoxy-2-butyl group, 5-phenoxy-1-pentyl group, 5-phenoxy-2-pentyl group, or can be a 6-phenoxy-1-hexyl, preferably, phenoxy - a (C ₁ -C ₄ alkyl) group, Preferably a phenoxymethyl group or phenoxyethyl group, and most preferably a phenoxymethyl group.

The “phenoxyphenyl- (C ₁ -C ₆ alkyl) group” in A ¹ of formula (I) is the above C ₁ -C ₆ alkyl group substituted with one phenoxyphenyl group, for example, phenoxyphenyl methyl Group [for example, (2-phenoxyphenyl) methyl group, (3-phenoxyphenyl) methyl group, (4-phenoxyphenyl) methyl group], phenoxyethyl group [for example, 1- (2-phenoxyphenyl) ethyl group, 1 -(3-phenoxyphenyl) ethyl group, 1- (4-phenoxyphenyl) ethyl group, 2- (2-phenoxyphenyl) ethyl group, 2- (3-phenoxyphenyl) ethyl group, 2- (4-phenoxyphenyl) ) Ethyl group], phenoxypropyl group [for example, 3- (2-phenoxyphenyl) -1-propyl group, 3- (3-phenoxyphenyl) -1-propyl group, 1- (4 Phenoxyphenyl) -1-propyl group, 2- (4-phenoxyphenyl) -1-propyl group, 3- (4-phenoxyphenyl) -1-propyl group, 2- (4-phenoxyphenyl) -2-propyl group ], 4- (4-phenoxyphenyl) -1-butyl group, 4- (4-phenoxyphenyl) -2-butyl group, 5- (4-phenoxyphenyl) -1-pentyl group, 5- (4-phenoxy) A phenyl) -2-pentyl group or a 6- (4-phenoxyphenyl) -1-hexyl group, preferably a phenoxyphenyl- (C ₁ -C ₄ alkyl) group, more preferably A phenoxyphenylmethyl group or a phenoxyphenylethyl group, and most preferably a phenoxyphenylmethyl group.

The “C ₃ -C ₈ cycloalkyl group” in A ¹ , A ² , substituent group α, and substituent group β of formula (I) and formula (Ia) is cyclic having 3 to 8 carbon atoms. an alkyl group, for example, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, or be a cyclooctyl group, preferably a C ₃ -C ₆ cycloalkyl group, more preferably Is a C ₄ -C ₆ cycloalkyl group, most preferably a cyclopentyl group or a cyclohexyl group.

In formula (I) and formula (Ia),
(I) A “4- to 8-membered heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom” in A ¹ ,
(Ii) the 4- to 8-membered heterocyclyl group, which is a substituent of the phenyl group in A ¹ , A ² , A ³ , A ^1a , A ^2a and A ^3a ,
(Iii) the 4- to 8-membered heterocyclyl group that is a substituent of the 5- to 6-membered aromatic heterocyclyl group in A ¹ , A ² , A ³ , A ^1a , A ^2a and A ^3a , and
(Iv) in the A ² "(nitrogen atom, oxygen atom and 1 to 4 to 8 membered heterocyclyl containing 4 atoms selected from the group consisting of sulfur atom) - (C ₁ -C ₆ alkyl) group" The 4- to 8-membered heterocyclyl moiety is a 4- to 8-membered heterocyclic group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom, such as a pyrrolyl group or a furyl group. , Thienyl, azepinyl, pyrazolyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyranyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl Group, azepinyl group, unsaturated heterocyclic group such as azosinyl group, azetidinyl group, Lysinyl group, pyrrolinyl group, imidazolidinyl group, imidazolinyl group, pyrazolidinyl group, pyrazolinyl group, piperidyl group, piperazinyl group, morpholinyl group, thiomorpholinyl group, perhydroazepinyl group, perhydroazosinyl group, 1,4,5,6 -The unsaturated heterocyclic group such as a tetrahydropyrimidinyl group, 1,2,3,6-tetrahydropyridyl group may be a partially or completely reduced group.

  In the case of (i) above, the 4- to 8-membered heterocyclyl group is preferably a 5- to 6-membered aromatic heterocyclyl group. In the case of (ii) and (iii), the 4- to 8-membered heterocyclyl group is preferably a 5- to 7-membered heterocyclyl group, more preferably a 5- to 6-membered aromatic heterocyclyl group, Preferred is a pyrrolyl, pyrazolyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, triazolyl or tetrazolyl group, most preferably a pyrrolyl, pyrazolyl, imidazolyl, triazolyl or tetrazolyl group. .

The “phenoxyphenyl group” in A ¹ of formula (I) can be, for example, a 2-phenoxyphenyl group, a 3-phenoxyphenyl group, or a 4-phenoxyphenyl group, and is preferably a 4-phenoxyphenyl group.

The “benzoylphenyl group” in A ¹ of formula (I) can be, for example, a 2-benzoylphenyl group, a 3-benzoylphenyl group, or a 4-benzoylphenyl group, and preferably a 4-benzoylphenyl group.

The “tetrahydronaphthyl group” in A ¹ and A ² of formula (I) can be, for example, a 1,2,3,4-tetrahydronaphthyl group.

The “dihydronaphthyl group” in A ¹ and A ² of formula (I) can be, for example, a 1,2-dihydronaphthyl group.

“1 to 4 atoms selected from the group consisting of nitrogen atom, oxygen atom and sulfur atom in A ¹ , A ² , A ³ , A ^1a , A ^2a and A ^3a of formula (I) and formula (Ia) A 5- to 6-membered aromatic heterocyclyl group containing is a 5- to 6-membered aromatic heterocyclic group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom; For example, it can be a furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyranyl, pyridyl, pyridazinyl, pyrimidinyl, or pyrazinyl group, and also 5-oxo- 4,5-dihydro-1H-1,2,4-triazolyl group, 5-thioxo-4,5-dihydro-1H Partially reduced 5- to 6-membered aromatics such as 1,2,4-triazolyl group, 2-oxo-1,2-dihydropyridyl group, 1,2-dioxo-2-thioxopyridyl group It may be a group having a carbonyl group or a thiocarbonyl group on the heterocyclic ring of the heterocyclic group. The 5- to 6-membered aromatic heterocyclyl group is preferably a 5- to 6-membered aromatic heterocyclyl group that contains one or more nitrogen atoms and may contain oxygen and sulfur atoms, and more preferably. Is a thiazolyl, isothiazolyl or pyridyl group, most preferably a pyridyl group.

“1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom in A ¹ , A ² , A ^2a , A ³ , and A ^3a of formula (I) and formula (Ia) The “containing 8- to 10-membered aromatic heterocyclyl group” is an 8- to 10-membered aromatic heterocyclic group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom. , Indolyl group, benzofuranyl group, benzothienyl group, benzimidazolyl group, benzisoxazolyl group, benzisoxazolyl group, benzothiazolyl group, benzisothiazolyl group, quinolyl group, isoquinolyl group, quinazolinyl group, quinoxalinyl group, benzo Oxadiazolyl group, benzothiadiazolyl group, pyrrolopyrrolyl group, pyrrolooxazolyl group, pyrrolothiazolyl group, pyrrolopyridyl Group, furopyrrolyl group, furopyridyl group, thienopyrrolyl group, thienopyridyl group, imidazopyrrolyl group, imidazoimidazolyl group, imidazooxazolyl group, imidazoisoxazolyl group, imidazothiazolyl group, imidazoisothiazolyl group, imidazopyridyl group Group, imidazopyridazinyl group, imidazopyrimidinyl group, imidazopyrazinyl group, oxazooxazolyl group, oxazoisoxazolyl group, oxazothiazolyl group, oxazoisothiazolyl group, oxazopyridyl group, It may be a thiazooxazolyl group, a thiazoisoxazolyl group, a thiazothiazolyl group, a thiazoisothiazolyl group, or a thiazopyridyl group, preferably containing one or more nitrogen atoms, oxygen atoms and sulfur A 9- to 10-membered aromatic heterocyclyl group that may contain atoms; Preferably, quinolyl, isoquinolyl, quinazolinyl, or quinoxalinyl group, most preferably a quinolyl group.

The “di (C ₁ -C ₆ alkyl) amino- (C ₁ -C ₆ alkyl) group” in A ² of formula (I) is one di (C ₁ -C ₆ alkyl) amino group (the alkyl Group is the same or different) substituted C ₁ -C ₆ alkyl group, for example, (dimethylamino) methyl group, (N-methyl-N-ethylamino) methyl group, (methylpropylamino) methyl Groups [for example, [N-methyl-N- (1-propyl) amino] methyl group, [N-methyl-N- (2-propyl) amino] methyl group], [N-methyl-N- (1-butyl) ) Amino] methyl group, (diethylamino) methyl group, (ethylpropylamino) methyl group [for example, [N-ethyl-N- (1-propyl) amino] methyl group, [N-ethyl-N- (2-propyl) ) Amino] methyl group], (dipropylamino) ) Methyl group [eg, [di (1-propyl) amino] methyl group, [di (2-propyl) amino] methyl group], [di (1-butyl) amino] methyl group, [di (1-pentyl)] Amino] methyl group, [di (1-hexyl) amino] methyl group, (dimethylamino) ethyl group [eg, 1- (dimethylamino) ethyl group, 2- (dimethylamino) ethyl group], 2- (N— Methyl-N-ethylamino) ethyl group, 2- [N-methyl-N- (1-propyl) amino] ethyl group, 2- [N-methyl-N- (1-butyl) amino] ethyl group, (diethylamino) ) Ethyl group [eg, 1- (diethylamino) ethyl group, 2- (diethylamino) ethyl group], 2- [N-ethyl-N- (1-propyl) amino] ethyl group, (dipropylamino) ethyl group [ For example, 2 -[Di (1-propylamino)] ethyl group and the like], 2- [di (1-butyl) amino] ethyl group, 2- [di (1-pentyl) amino] ethyl group, 2- [di (1- (Hexyl) amino] ethyl group, 1,2-di (dimethylamino) ethyl group, (dimethylamino) propyl group (for example, 1-dimethylamino-1-propyl group, 2-dimethylamino-1-propyl group, 3- Dimethylamino-1-propyl group, 1-dimethylamino-2-propyl group, 2-dimethylamino-2-propyl group, etc.), (diethylamino) propyl group (for example, 3-diethylamino-1-propyl group, etc.), ( Dipropylamino) propyl group [eg, 3- [di (1-propyl) amino] -1-propyl group, etc.], 3- [di (1-butyl) amino] -1-propyl group, 2,3-di (Dimethyl Mino) -1-propyl group, 1-dimethylamino-1-butyl group, 2-dimethylamino-1-butyl group, 3-dimethylamino-1-butyl group, 4-dimethylamino-1-butyl group, 4- Diethylamino-1-butyl group, 1-dimethylamino-2-butyl group, 3-dimethylamino-2-butyl group, 4-dimethylamino-2-butyl group, 3-dimethylamino-2-methyl-1-propyl group 1-dimethylamino-2-methyl-2-propyl group, 2,3-di (dimethylamino) -1-butyl group, 2,4-di (dimethylamino) -1-butyl group, 3,4-di (Dimethylamino) -1-butyl group, 5-dimethylamino-1-pentyl group, 5-dimethylamino-2-pentyl group, 5-dimethylamino-3-pentyl group, 4,5-di (dimethylamino)- 1-pen Group, 3,4,5-tri (dimethylamino) -1-pentyl group, 4-dimethylamino-2-methyl-2-butyl group, 4-dimethylamino-3-methyl-2-butyl group, 3- Dimethylamino-2,2-dimethyl-1-propyl group, 6-dimethylamino-1-hexyl group, 6-dimethylamino-2-hexyl group, 6-dimethylamino-3-hexyl group, 5-dimethylamino-2 -Methyl-1-pentyl group, 5-dimethylamino-3-methyl-1-pentyl group, 4-dimethylamino-2-ethyl-1-butyl group, 4-dimethylamino-2,2-dimethyl-1-butyl Group, 4-dimethylamino-2,3-dimethyl-1-butyl group, or 5,6-di (dimethylamino) -1-hexyl group, preferably dialkylamino C ₁ -C ₄ alkyl Group Alkylamino C ₁ -C ₄ alkyl groups, one di (C ₁ -C ₄ alkyl) amino group (said alkyl group may be the same or different) be showing a C ₁ -C ₄ alkyl group substituted with] More preferably, (dimethylamino) methyl, (diethylamino) methyl, (dipropylamino) methyl, (dimethylamino) ethyl, (diethylamino) ethyl, (dipropylamino) ethyl, (dimethyl) Amino) propyl group, (diethylamino) propyl group, or (dipropylamino) propyl group, most preferably (dimethylamino) methyl group or (dimethylamino) ethyl group [especially 2- (dimethylamino) Ethyl group].

The “(C ₁ -C ₆ alkylthio)-(C ₁ -C ₆ alkyl) group” in A ² of formula (I) is the above C ₁ -C substituted with one of the following C ₁ -C ₆ alkylthio groups. ₆ alkyl group, for example, methylthiomethyl group, ethylthiomethyl group, propylthiomethyl group [for example, (1-propylthio) methyl group, (2-propylthio) methyl group], butylthiomethyl group [for example, (1 -Butylthio) methyl group and the like], (1-pentylthio) methyl group, (1-hexylthio) methyl group, methylthioethyl group [eg, 1- (methylthio) ethyl group, 2- (methylthio) ethyl group], ethylthioethyl Group [for example, 2- (ethylthio) ethyl group and the like], propylthioethyl group [for example, 2- (1-propylthio) ethyl group and the like], butylthioethyl group [for example, 2- (1-buty Thio) ethyl group and the like], 2- (1-pentylthio) ethyl group, 2- (1-hexylthio) ethyl group, 1,2-di (methylthio) ethyl group, methylthiopropyl group [for example, 1-methylthio-1- Propyl group, 2-methylthio-1-propyl group, 3-methylthio-1-propyl group, 1-methylthio-2-propyl group and the like], ethylthiopropyl group [for example, 3-ethylthio-1-propyl group and the like], Propylthiopropyl group [for example, 3- (1-propylthio) -1-propyl group and the like], butylthiopropyl group [for example, 3- (1-butylthio) -1-propyl group and the like], 1-methylthio-1- Butyl group, 2-methylthio-1-butyl group, 3-methylthio-1-butyl group, 4-methylthio-1-butyl group, 4-ethylthio-1-butyl group, 1-methylthio 2-butyl group, 3-methylthio-2-butyl group, 4-methylthio-2-butyl group, 3-methylthio-2-methyl-1-propyl group, 1-methylthio-2-methyl-2-propyl group, 5 -Methylthio-1-pentyl group, 5-methylthio-2-pentyl group, 5-methylthio-3-pentyl group, 4-methylthio-2-methyl-2-butyl group, 4-methylthio-3-methyl-2-butyl Group, 6-methylthio-1-hexyl group, 6-methylthio-2-hexyl group, 6-methylthio-3-hexyl group, 5-methylthio-2-methyl-1-pentyl group, 5-methylthio-3-methyl- 1-pentyl group, 4-methylthio-2-ethyl-1-butyl group, 4-methylthio-2,2-dimethyl-1-butyl group, or 4-methylthio-2,3-dimethyl-1-butyl Be a group, suitably alkylthio C ₁ -C ₄ alkyl group (said alkylthio C ₁ -C ₄ alkyl groups, one C ₁ -C ₄ C ₁ -C ₄ alkyl group substituted with an alkylthio group And more preferably a methylthiomethyl group, an ethylthiomethyl group, a propylthiomethyl group, a methylthioethyl group, an ethylthioethyl group, a propylthioethyl group, a methylthiopropyl group, an ethylthiopropyl group, or A propylthiopropyl group, most preferably a methylthiomethyl group or a methylthioethyl group [particularly a 2- (methylthio) ethyl group].

“(4- to 8-membered heterocyclyl containing 1 to 4 atoms selected from the group consisting of nitrogen atom, oxygen atom and sulfur atom)-(C ₁ -C ₆ alkyl) group in A ² of formula (I) "Is a C ₁ -C ₆ alkyl substituted with _one above (a 4 to 8 membered heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom). Groups such as furylmethyl, furylethyl, furylpropyl, furylbutyl, furylpentyl, furylhexyl, thienylmethyl, thienylethyl, thienylpropyl, thienylbutyl, thienylpentyl, thienyl Hexyl, pyrrolylmethyl, pyrrolylethyl, pyrrolylpropyl, pyrazolylmethyl, imidazolylmethyl, oxazolylmethyl Isoxazolylmethyl group, thiazolylmethyl group, thiazolylethyl group, thiazolylpropyl group, thiazolylbutyl group, thiazolylpentyl group, thiazolylhexyl group, isothiazolylmethyl group, 1,2,3-oxadiazolylmethyl group 1,2,3-thiadiazolylmethyl group, triazolylmethyl group, tetrazolylmethyl group, pyranylmethyl group, pyridylmethyl group, pyridylethyl group, pyridylpropyl group, pyridylbutyl group, pyridylpentyl group, pyridylhexyl Group, pyridazinylmethyl group, pyrimidinylmethyl group, pyrazinylmethyl group, azepinylmethyl group, azosinylmethyl group, indolylmethyl group, benzofuranylmethyl group, benzothienylmethyl group, benzothienylethyl group, benzothienylpropyl group, benzoimidazolylmethyl , Benzoisoxazolylmethyl group, benzoisoxazolylmethyl group, benzothiazolylmethyl group, benzothiazolylethyl group, benzothiazolylpropyl group, benzoisothiazolylmethyl group, quinolylmethyl group, isoquino Rylmethyl, quinazolinylmethyl, quinoxalinylmethyl, pyrrolidinylmethyl, pyrrolidinylethyl, pyrrolidinylpropyl, pyrrolidinylbutyl, pyrrolidinylpentyl, pyrrolidinylhexyl Group, pyrrolinylmethyl group, imidazolidinylmethyl group, imidazolinylmethyl group, pyrazolidinylmethyl group, pyrazolinylmethyl group, piperidylmethyl group, piperidylethyl group, piperidylpropyl group, piperazinylmethyl group, Morpholinylmethyl group, morpholinylethyl group, morpholinylpropyl group, Can be a thiomorpholinylmethyl group, a thiomorpholinylethyl group, a thiomorpholinylpropyl group, a perhydroazepinylmethyl group, a perhydroazosinylmethyl group, a tetrahydropyridylmethyl group, or a tetrahydropyrimidinylmethyl group preferably, (5 to 7-membered saturated heterocyclyl) - a (C ₁ -C ₄ alkyl) group, more preferably, pyrrolidyl - (C ₁ -C ₃ alkyl) group, piperidyl - (C ₁ -C ₃ alkyl) group, piperazyl- (C ₁ -C ₃ alkyl) group, morpholyl- (C ₁ -C ₃ alkyl) group, or thiomorpholyl- (C ₁ -C ₃ alkyl) group, more preferably A pyrrolidylmethyl group, a pyrrolidylethyl group, a piperidylmethyl group, or a piperidylethyl group;

The “naphthylmethyl group” in A ³ of formula (I) can be, for example, a 1-naphthylmethyl group or a 2-naphthylmethyl group.

The “halogeno C ₁ -C ₆ alkyl group” in Substituent Group α and Substituent Group β of Formula (I) and Formula (Ia) is the above C ₁ -C ₆ substituted with 1 to 7 of the following halogeno groups: An alkyl group, for example, fluoromethyl group, difluoromethyl group, dichloromethyl group, dibromomethyl group, trifluoromethyl group, trichloromethyl group, 2-fluoroethyl group, 2-bromoethyl group, 2-chloroethyl group, 2- Iodoethyl group, 2,2-difluoroethyl group, 2,2,2-trifluoroethyl group, trichloroethyl group, pentafluoroethyl group, 3-fluoropropyl group, 3-chloropropyl group, 4-fluorobutyl group, 5 - fluoropentyl group or can be a 6-fluoro-hexyl group, preferably a, C ₁ -C ₄ alkyl groups der substituted with 1 to 5 halogeno groups More preferred are a fluoromethyl group, a chloromethyl group, a difluoromethyl group, a trifluoromethyl group, or a pentafluoroethyl group, and most preferred is a trifluoromethyl group.

The “hydroxy C ₁ -C ₆ alkyl group” in the substituent group α of the formula (I) and the formula (Ia) is the above C ₁ -C ₆ alkyl group substituted with 1 to 4 hydroxyl groups. Hydroxymethyl group, hydroxyethyl group (for example, 1-hydroxyethyl group, 2-hydroxyethyl group), dihydroxyethyl group (for example, 1,2-dihydroxyethyl group, etc.), hydroxypropyl group (for example, 1-hydroxy-1 -Propyl group, 2-hydroxy-1-propyl group, 3-hydroxy-1-propyl group, 1-hydroxy-2-propyl group, etc.), dihydroxypropyl group (for example, 2,3-dihydroxy-1-propyl group, etc.) ), Hydroxybutyl groups (for example, 1-hydroxy-1-butyl group, 2-hydroxy-1-butyl group, 3-hydroxy-1-butyl group, 4-hydroxy Loxy-1-butyl group, 1-hydroxy-2-butyl group, 3-hydroxy-2-butyl group, 4-hydroxy-2-butyl group, etc.), 3-hydroxy-2-methyl-1-propyl group, 1 -Hydroxy-2-methyl-2-propyl group, dihydroxybutyl group (for example, 2,3-dihydroxy-1-butyl group, 2,4-dihydroxy-1-butyl group, 3,4-dihydroxy-1-butyl group) Etc.), 5-hydroxy-1-pentyl group, 5-hydroxy-2-pentyl group, 5-hydroxy-3-pentyl group, 4,5-dihydroxy-1-pentyl group, 3,4,5-trihydroxy- 1-pentyl group, 4-hydroxy-2-methyl-2-butyl group, 4-hydroxy-3-methyl-2-butyl group, 6-hydroxy-1-hexyl group, 6-hydroxy-2-hexyl group, 6 -Hydroxy-3-hexyl group, 5-hydroxy-2-methyl-1-pentyl group, 5-hydroxy-3-methyl-1-pentyl group, 4-hydroxy-2-ethyl-1-butyl group, 4-hydroxy -2,2-dimethyl-1-butyl group, 4-hydroxy-2,3-dimethyl-1-butyl group, or 5,6-dihydroxy-1-hexyl group, preferably hydroxy C ₁ A —C ₄ alkyl group (the hydroxy C ₁ -C ₄ alkyl group represents a C ₁ -C ₄ alkyl group substituted with 1 to 3 hydroxyl groups), and more preferably a hydroxymethyl group, a hydroxy group An ethyl group, a dihydroxyethyl group, a hydroxypropyl group, a dihydroxypropyl group, a hydroxybutyl group, or a dihydroxybutyl group, and more preferably a hydroxymethyl group or Hydroxyethyl group.

The “aminosulfonyl C ₁ -C ₆ alkyl group” in the substituent group α of the formula (I) and the formula (Ia) is the above C ₁ -C substituted with one aminosulfonyl group (—SO ₂ NH ₂ ). ₆ alkyl group, for example, aminosulfonylmethyl group, aminosulfonylethyl group (for example, 1-aminosulfonylethyl group or 2-aminosulfonylethyl group), aminosulfonylpropyl group (for example, 1-aminosulfonyl-1-propyl) Group, 2-aminosulfonyl-1-propyl group, 3-aminosulfonyl-1-propyl group, 1-aminosulfonyl-2-propyl group or 2-aminosulfonyl-2-propyl group), 4-aminosulfonyl- 1-butyl group, 4-aminosulfonyl-2-butyl group, 5-aminosulfonyl-1-pentyl group, 5-aminosulfonyl-2 Pentyl or, can be a 6-aminosulfonyl-1-hexyl group, preferably, aminosulfonyl - a (C ₁ -C ₄ alkyl) group, more preferably, aminosulfonyl methyl or aminosulfonyl ethyl A group, most preferably an aminosulfonylmethyl group.

The “(C ₁ -C ₆ alkyl) aminosulfonyl- (C ₁ -C ₆ alkyl) group” in the substituent group α of the formula (I) and the formula (Ia) represents the aminosulfonyl C ₁ -C ₆ alkyl group. A group in which a nitrogen atom is substituted with _one C ₁ -C ₆ alkyl group, for example, a methylaminosulfonylmethyl group, an ethylaminosulfonylmethyl group, a propylaminosulfonylmethyl group [for example, (1-propyl) amino Sulfonylmethyl group, (2-propyl) aminosulfonylmethyl group], butylaminosulfonylmethyl group [for example, (1-butyl) aminosulfonylmethyl group, etc.], (1-pentyl) aminosulfonylmethyl group, (1-hexyl) Aminosulfonylmethyl group, methylaminosulfonylethyl group [for example, 1- (methylaminosulfonyl) ethyl group, 2- (methyl) Aminosulfonyl) ethyl group], ethylaminosulfonylethyl group [for example, 2- (ethylaminosulfonyl) ethyl group and the like], propylaminosulfonylethyl group [for example, 2-[(1-propyl) aminosulfonyl] ethyl group and the like] , Butylaminosulfonylethyl group [for example, 2-[(1-butyl) aminosulfonyl] ethyl group and the like], 2-[(1-pentyl) aminosulfonyl] ethyl group, 2-[(1-hexyl) aminosulfonyl] Ethyl group, methylaminosulfonylpropyl group [for example, 1-methylaminosulfonyl-1-propyl group, 2-methylaminosulfonyl-1-propyl group, 3-methylaminosulfonyl-1-propyl group, 1-methylaminosulfonyl- 2-propyl group and the like], ethylaminosulfonylpropyl group [for example, 3-ethylaminosulfonyl-1-propyl group and the like], propylaminosulfonylpropyl group [for example, 3-[(1-propyl) aminosulfonyl] -1-propyl group and the like], butylaminosulfonylpropyl group [for example, 3- [(1-butyl) aminosulfonyl] -1-propyl group and the like], 1-methylaminosulfonyl-1-butyl group, 2-methylaminosulfonyl-1-butyl group, 3-methylaminosulfonyl-1-butyl group, 4-methylaminosulfonyl-1-butyl group, 4-ethylaminosulfonyl-1-butyl group, 1-methylaminosulfonyl-2-butyl group, 3-methylaminosulfonyl-2-butyl group, 4-methylaminosulfonyl- 2-butyl group, 3-methylaminosulfonyl-2-methyl-1-propyl group, 1-methylaminos Honyl-2-methyl-2-propyl group, 5-methylaminosulfonyl-1-pentyl group, 5-methylaminosulfonyl-2-pentyl group, 5-methylaminosulfonyl-3-pentyl group, 4-methylaminosulfonyl- 2-methyl-2-butyl group, 4-methylaminosulfonyl-3-methyl-2-butyl group, 6-methylaminosulfonyl-1-hexyl group, 6-methylaminosulfonyl-2-hexyl group, 6-methylamino Sulfonyl-3-hexyl group, 5-methylaminosulfonyl-2-methyl-1-pentyl group, 5-methylaminosulfonyl-3-methyl-1-pentyl group, 4-methylaminosulfonyl-2-ethyl-1-butyl Group, 4-methylaminosulfonyl-2,2-dimethyl-1-butyl group, or 4-methylaminosulfonyl It is a 2,3-dimethyl-1-butyl group, preferably a, (C ₁ -C ₄ alkyl) aminosulfonyl - a (C ₁ -C ₄ alkyl) group, more preferably, methylaminosulfonyl Methyl group, ethylaminosulfonylmethyl group, propylaminosulfonylmethyl group, methylaminosulfonylethyl group, ethylaminosulfonylethyl group, propylaminosulfonylethyl group, methylaminosulfonylpropyl group, ethylaminosulfonylpropyl group, or propylaminosulfonyl A propyl group, and most preferably a methylaminosulfonylmethyl group or a methylaminosulfonylethyl group [particularly 2- (methylaminosulfonyl) ethyl group].

Formula (I) and "hydroxyimino C ₁ -C ₆ alkyl group" in Substituent group α in the formula (Ia), one of hydroxyimino groups (= NOH) the C ₁ -C ₆ alkyl group substituted with For example, a hydroxyiminomethyl group, a hydroxyiminoethyl group (for example, 1-hydroxyiminoethyl group or 2-hydroxyiminoethyl group), a hydroxyiminopropyl group (for example, 1-hydroxyimino-1-propyl group, 2 -Hydroxyimino-1-propyl group, 3-hydroxyimino-1-propyl group, 1-hydroxyimino-2-propyl group or 2-hydroxyimino-2-propyl group), 4-hydroxyimino-1-butyl Group, 4-hydroxyimino-2-butyl group, 5-hydroxyimino-1-pentyl group, 5-hydroxyimino-2-pe Butyl group, or, it can be a 6-hydroxyimino-1-hexyl group, preferably, hydroxyimino - a (C ₁ -C ₄ alkyl) group, more preferably a hydroxyiminomethyl group or a hydroxyimino-ethyl It is a group.

The “(C ₁ -C ₆ alkoxyimino)-(C ₁ -C ₆ alkyl) group” in the substituent group α of the formula (I) and the formula (Ia) represents oxygen of the hydroxyimino C ₁ -C ₆ alkyl group. A group in which an atom is substituted with _one C ₁ -C ₆ alkyl group, for example, a methoxyiminomethyl group, an ethoxyiminomethyl group, a propoxyiminomethyl group [for example, a (1-propoxyimino) methyl group, ( 2-propoxyimino) methyl group], butoxyiminomethyl group [for example, (1-butoxyimino) methyl group etc.], (1-pentyloxyimino) methyl group, (1-hexyloxyimino) methyl group, methoxyiminoethyl Group [for example, 1- (methoxyimino) ethyl group, 2- (methoxyimino) ethyl group], ethoxyiminoethyl group [for example, 2- (ethoxyimino) ethyl group, etc. , Propoxyiminoethyl group [eg 2- (1-propoxyimino) ethyl group etc.], butoxyiminoethyl group [eg 2- (1-butoxyimino) ethyl group etc.], 2- (1-pentyloxyimino) Ethyl group, 2- (1-hexyloxyimino) ethyl group, methoxyiminopropyl group [for example, 1-methoxyimino-1-propyl group, 2methoxyimino-1-propyl group, 3-methoxyimino-1-propyl group , 1-methoxyimino-2-propyl group, etc.], ethoxyiminopropyl group [eg, 3-ethoxyimino-1-propyl group, etc.], propoxyiminopropyl group [eg, 3- (1-propoxyimino) -1- Propyl group, etc.], butoxyiminopropyl group [eg, 3- (1-butoxyimino) -1-propyl group, etc.], 1-methoxy Cimino-1-butyl group, 2-methoxyimino-1-butyl group, 3-methoxyimino-1-butyl group, 4-methoxyimino-1-butyl group, 4-ethoxyimino-1-butyl group, 1-methoxy Imino-2-butyl group, 3-methoxyimino-2-butyl group, 4-methoxyimino-2-butyl group, 3-methoxyimino-2-methyl-1-propyl group, 1-methoxyimino-2-methyl- 2-propyl group, 5-methoxyimino-1-pentyl group, 5-methoxyimino-2-pentyl group, 5-methoxyimino-3-pentyl group, 4-methoxyimino-2-methyl-2-butyl group, 4 -Methoxyimino-3-methyl-2-butyl group, 6-methoxyimino-1-hexyl group, 6-methoxyimino-2-hexyl group, 6-methoxyimino-3-hexyl group, -Methoxyimino-2-methyl-1-pentyl group, 5-methoxyimino-3-methyl-1-pentyl group, 4-methoxyimino-2-ethyl-1-butyl group, 4-methoxyimino-2,2- It may be a dimethyl-1-butyl group or a 4-methoxyimino-2,3-dimethyl-1-butyl group, preferably (C ₁ -C ₄ alkoxyimino)-(C ₁ -C ₄ alkyl) More preferably a methoxyiminomethyl group, an ethoxyiminomethyl group, a propoxyiminomethyl group, a methoxyiminoethyl group, an ethoxyiminoethyl group, a propoxyiminoethyl group, a methoxyiminopropyl group, an ethoxyiminopropyl group, or , A propoxyiminopropyl group, most preferably a methoxyiminomethyl group or a methoxyiminoethyl group [in particular, 2- (methoxy Imino) is an ethyl group].

The “C ₂ -C ₆ alkynyl group” in the substituent group α of the formula (I) and the formula (Ia) is an alkynyl group having 2 to 6 carbon atoms having one carbon-carbon triple bond, for example, ethynyl, be a 2-propynyl, 2-butynyl, 2-pentynyl or 2-hexynyl group, preferably is C ₂ -C ₄ alkynyl group, more preferably, be a C ₂ -C ₃ alkynyl group More preferably, they are an ethynyl group or a 1-propynyl group.

“C ₁ -C ₆ alkoxy group” in substituent group α and substituent group β of formula (I) and formula (Ia), and R ^{3 in} the group having the formula —OCH ₂ COR ³ of substituent group α The “C ₁ -C ₆ alkoxy group” is a hydroxyl group substituted with the above C ₁ -C ₆ alkyl group. 2-butoxy group, 2-methyl-1-propoxy group, 2-methyl-2-propoxy group, 1-pentyloxy group, 2-pentyloxy group, 3-pentyloxy group, 2-methyl-2-butoxy group, 3-methyl-2-butoxy group, 1-hexyloxy group, 2-hexyloxy group, 3-hexyloxy group, 2-methyl-1-pentyloxy group, 3-methyl-1-pentyloxy group, 2-ethyl -1-butoxy group It can be a 2,2-dimethyl-1-butoxy group or a 2,3-dimethyl-1-butoxy group, preferably a C ₁ -C ₄ alkoxy group, more preferably a methoxy group or An ethoxy group, most preferably a methoxy group.

“Halogeno C ₁ -C ₆ alkoxy group” in Substituent Group α and Substituent Group β in Formula (I) and Formula (Ia) is a hydroxyl group substituted with the above halogeno C ₁ -C ₆ alkyl group, for example, , Fluoromethoxy group, difluoromethoxy group, dichloromethoxy group, dibromomethoxy group, trifluoromethoxy group, trichloromethoxy group, 2-fluoroethoxy group, 2-bromoethoxy group, 2-chloroethoxy group, 2-iodoethoxy group, 2,2-difluoroethoxy group, 2,2,2-trifluoroethoxy group, trichloroethoxy group, pentafluoroethoxy group, 3-fluoropropoxy group, 3-chloropropoxy group, 4-fluorobutoxy group, 5-fluoropentyl It can be an oxy group or a 6-fluorohexyloxy group, preferably 1 to 5 halogeno groups In a substituted C ₁ -C ₄ alkyl group, more preferably a fluoromethyl group, chloromethyl group, difluoromethyl group, trifluoromethyl group, or a pentafluoroethyl group, and most preferably, A trifluoromethyl group.

In the substituent group α and the substituent group β of the formula (I) and the formula (Ia), the “C ₂ -C ₇ alkylcarbonyloxy group” means that the carbon atom of the carbonyloxy group (—COO—) is the above C ₁ — A group substituted with a C ₆ alkyl group, for example, methylcarbonyloxy group, ethylcarbonyloxy group, 1-propylcarbonyloxy group, 2-propylcarbonyloxy group, 1-butylcarbonyloxy group, 2-butylcarbonyloxy group Group, 2-methyl-1-propylcarbonyloxy group, 2-methyl-2-propylcarbonyloxy group, 1-pentylcarbonyloxy group, 2-pentylcarbonyloxy group, 3-pentylcarbonyloxy group, 2-methyl-2 -Butylcarbonyloxy group, 3-methyl-2-butylcarbonyloxy group, 1-hexylcarbonyloxy group, 2-hexylcarbonyloxy group, 3-hexylcarbonyloxy group, 2-methyl-1-pentylcarbonyloxy group, 3-methyl-1-pentylcarbonyloxy group, 2-ethyl-1-butylcarbonyloxy group, 2,2 - dimethyl-1-butyl carbonyloxy group, or a 2,3-dimethyl-1-butyl carbonyloxy group, preferably a C ₂ -C ₅ alkylcarbonyloxy group, and more preferably, methylcarbonyl An oxy group or an ethylcarbonyloxy group, and most preferably a methylcarbonyloxy group.

“C ₁ -C ₆ alkylthio group” in Substituent Group α and Substituent Group β in Formula (I) and Formula (Ia) is a mercapto group substituted with the above C ₁ -C ₆ alkyl group, for example, Methylthio group, ethylthio group, 1-propylthio group, 2-propylthio group, 1-butylthio group, 2-butylthio group, 2-methyl-1-propylthio group, 2-methyl-2-propylthio group, 1-pentylthio group, 2 -Pentylthio group, 3-pentylthio group, 2-methyl-2-butylthio group, 3-methyl-2-butylthio group, 1-hexylthio group, 2-hexylthio group, 3-hexylthio group, 2-methyl-1-pentylthio group 3-methyl-1-pentylthio group, 2-ethyl-1-butylthio group, 2,2-dimethyl-1-butylthio group, or 2,3-dimethyl-1-butylthio group And is preferably a C ₁ -C ₄ alkylthio group, more preferably a methylthio group or an ethylthio group, and most preferably a methylthio group.

The “C ₁ -C ₆ alkylsulfinyl group” in the substituent group α and the substituent group β of the formula (I) and the formula (Ia) is a sulfinyl group (—SO——) substituted with the C ₁ -C ₆ alkyl group. For example, methanesulfinyl group, ethanesulfinyl group, 1-propanesulfinyl group, 2-propanesulfinyl group, 1-butanesulfinyl group, 2-butanesulfinyl group, 2-methyl-1-propanesulfinyl group, 2- Methyl-2-propanesulfinyl group, 1-pentanesulfinyl group, 2-pentanesulfinyl group, 3-pentanesulfinyl group, 2-methyl-2-butanesulfinyl group, 3-methyl-2-butanesulfinyl group, 1-hexanesulfinyl group Group, 2-hexanesulfinyl group, 3-hexanesulfinyl group, 2-methyl-1-pentane Rufinyl group, 3-methyl-1-pentanesulfinyl group, 2-ethyl-1-butanesulfinyl group, 2,2-dimethyl-1-butanesulfinyl group, or 2,3-dimethyl-1-butanesulfinyl group It is preferably a C ₁ -C ₄ alkylsulfinyl group, more preferably a methanesulfinyl group or an ethanesulfinyl group, and most preferably a methanesulfinyl group.

The “C ₁ -C ₆ alkylsulfonyl group” in the substituent group α and the substituent group β of the formula (I) and the formula (Ia) is a sulfonyl group (—SO ₂ ) substituted with the C ₁ -C ₆ alkyl group. -), For example, methanesulfonyl group, ethanesulfonyl group, 1-propanesulfonyl group, 2-propanesulfonyl group, 1-butanesulfonyl group, 2-butanesulfonyl group, 2-methyl-1-propanesulfonyl group, 2 -Methyl-2-propanesulfonyl group, 1-pentanesulfonyl group, 2-pentanesulfonyl group, 3-pentanesulfonyl group, 2-methyl-2-butanesulfonyl group, 3-methyl-2-butanesulfonyl group, 1-hexane Sulfonyl group, 2-hexanesulfonyl group, 3-hexanesulfonyl group, 2-methyl-1-pentanesulfonyl group, 3-methyl-1-pen Nsuruhoniru group, 2-ethyl-1-butanesulfonyl group, 2,2-dimethyl-1-butanesulfonyl group, or may be a 2,3-dimethyl-1-butanesulfonyl group, preferably a, C ₁ - a C ₄ alkylsulfonyl group, more preferably a methanesulfonyl group or an ethanesulfonyl group, and most preferably a methanesulfonyl group.

The “C ₁ -C ₆ alkylaminosulfonyl group” in the substituent group α of the formula (I) and the formula (Ia) means that the nitrogen atom of the aminosulfonyl group (—SO ₂ NH—) is the above C ₁ -C ₆ alkyl. Groups substituted with a group such as methylaminosulfonyl group, ethylaminosulfonyl group, 1-propylaminosulfonyl group, 2-propylaminosulfonyl group, 1-butylaminosulfonyl group, 2-butylaminosulfonyl group, 2 -Methyl-1-propylaminosulfonyl group, 2-methyl-2-propylaminosulfonyl group, 1-pentylaminosulfonyl group, 2-pentylaminosulfonyl group, 3-pentylaminosulfonyl group, 2-methyl-2-butylamino Sulfonyl group, 3-methyl-2-butylaminosulfonyl group, 1-hexylaminosulfonyl group, 2-hexyl Minosulfonyl group, 3-hexylaminosulfonyl group, 2-methyl-1-pentylaminosulfonyl group, 3-methyl-1-pentylaminosulfonyl group, 2-ethyl-1-butylaminosulfonyl group, 2,2-dimethyl- It may be a 1-butylaminosulfonyl group or a 2,3-dimethyl-1-butylaminosulfonyl group, preferably a C ₁ -C ₄ alkylaminosulfonyl group, more preferably a methylaminosulfonyl group Or an ethylaminosulfonyl group, and most preferably a methylaminosulfonyl group.

“C ₁ -C ₆ alkylamino group” in substituent group α and substituent group β of formula (I) and formula (Ia), and R ^{3 in the} group having the formula —OCH ₂ COR ³ of substituent group α “C ₁ -C ₆ alkylamino group” is an amino group substituted by one of the above C ₁ -C ₆ alkyl groups, for example, methylamino group, ethylamino group, propylamino group (for example, 1 -Propylamino group, 2-propylamino group), 1-butylamino group, 2-butylamino group, 2-methyl-1-propylamino group, 2-methyl-2-propylamino group, 1-pentylamino group, 2-pentylamino group, 3-pentylamino group, 2-methyl-2-butylamino group, 3-methyl-2-butylamino group, 1-hexylamino group, 2-hexylamino group, 3-hexylamino group, 2-methyl -1-pentylamino group, 3-methyl-1-pentylamino group, 2-ethyl-1-butylamino group, 2,2-dimethyl-1-butylamino group, or 2,3-dimethyl-1-butyl obtained an amino group, preferably a C ₁ -C ₄ alkylamino group, more preferably a methylamino group, an ethylamino group or a propylamino group, and more preferably, methylamino or ethyl An amino group, most preferably a methylamino group.

Substituent group α and substituent group β “di (C ₁ -C ₆ alkyl) amino group” of formula (I) and formula (Ia), and groups having the formula —OCH ₂ COR ³ of substituent group α The “di (C ₁ -C ₆ alkyl) amino group” of R ³ is an amino group substituted with the same or different two C ₁ -C ₆ alkyl groups, for example, dimethylamino group, methylethylamino Group, methylpropylamino group [for example, N- (1-propyl) -N-methylamino group and the like], methylbutylamino group [for example, N- (1-butyl) -N-methylamino group and the like], diethylamino group , Ethylpropylamino group [for example, N- (1-propyl) -N-ethylamino group, etc.], dipropylamino group [for example, di (1-propyl) amino group, di (2-propyl) amino group, etc.] Di (1-butyl) amino group, di (2-butyl) a Group, di (2-methyl-1-propyl) amino group, di (2-methyl-2-propyl) amino group, di (1-pentyl) amino group, di (2-pentyl) amino group, di (3 -Pentyl) amino group, di (2-methyl-1-butyl) amino group, di (2-ethyl-1-propyl) amino group, di (1-hexyl) amino group, di (2-hexyl) amino group, Di (3-hexyl) amino group, di (2-methyl-1-pentyl) amino group, di (3-methyl-1-pentyl) amino group, di (4-methyl-1-pentyl) amino group, di ( 2-methyl-2-pentyl) amino group, di (3-methyl-2-pentyl) amino group, di (4-methyl-2-pentyl) amino group, di (2,2-dimethyl-1-butyl) amino Group, di (3,3-dimethyl-1-butyl) amino group, di (2,3-dimethyl-1-butyl) amino group, or di (2- Til-1-butyl) amino group, preferably a di (C ₁ -C ₄ alkyl) amino group (the alkyl groups being the same or different), more preferably a dimethylamino group, methyl An ethylamino group, a methylpropylamino group, a diethylamino group, an ethylpropylamino group, or a dipropylamino group, more preferably a dimethylamino group or a diethylamino group, and most preferably a dimethylamino group. .

In the substituent group α and the substituent group β of the formula (I) and the formula (Ia), the “C ₂ -C ₇ alkylcarbonylamino group” means that the carbon atom of the carbonylamino group (—CONH—) is the above C ₁ — A group substituted with a C ₆ alkyl group, for example, methylcarbonylamino group, ethylcarbonylamino group, 1-propylcarbonylamino group, 2-propylcarbonylamino group, 1-butylcarbonylamino group, 2-butylcarbonylamino Group, 2-methyl-1-propylcarbonylamino group, 2-methyl-2-propylcarbonylamino group, 1-pentylcarbonylamino group, 2-pentylcarbonylamino group, 3-pentylcarbonylamino group, 2-methyl-2 -Butylcarbonylamino group, 3-methyl-2-butylcarbonylamino group, 1-hexylcarbonylamino group 2-hexylcarbonylamino group, 3-hexylcarbonylamino group, 2-methyl-1-pentylcarbonylamino group, 3-methyl-1-pentylcarbonylamino group, 2-ethyl-1-butylcarbonylamino group, 2,2 - dimethyl-1-butylcarbonylamino group, or, can be a 2,3-dimethyl-1-butylcarbonylamino group, preferably a C ₂ -C ₅ alkylcarbonylamino group, more preferably, methyl A carbonylamino group or an ethylcarbonylamino group, and most preferably a methylcarbonylamino group.

In the substituent group α and the substituent group β of the formula (I) and the formula (Ia), “C ₂ -C ₇ alkoxycarbonylamino group” means that the carbon atom of the carbonylamino group (—CONH—) is the above C ₁ — A group substituted with a C ₆ alkoxy group, for example, a methoxycarbonylamino group, an ethoxycarbonylamino group, a 1-propoxycarbonylamino group, a 2-propoxycarbonylamino group, a 1-butoxycarbonylamino group, a 2-butoxycarbonylamino group; Group, 2-methyl-1-propoxycarbonylamino group, 2-methyl-2-propoxycarbonylamino group, 1-pentyloxycarbonylamino group, 2-pentyloxycarbonylamino group, 3-pentyloxycarbonylamino group, 2- Methyl-2-butoxycarbonylamino group, 3-methyl-2-butoxycarbonyl Amino group, 1-hexyloxycarbonylamino group, 2-hexyloxycarbonylamino group, 3-hexyloxycarbonylamino group, 2-methyl-1-pentyloxycarbonylamino group, 3-methyl-1-pentyloxycarbonylamino group , 2-ethyl-1-butoxycarbonylamino group, 2,2-dimethyl-1-butoxycarbonylamino group, or 2,3-dimethyl-1-butoxycarbonylamino group, preferably C _2- A C ₅ alkoxycarbonylamino group, more preferably a methoxycarbonylamino group or an ethoxycarbonylamino group, and most preferably a methoxycarbonylamino group.

The “C ₁ -C ₆ alkylsulfonylamino group” in the substituent group α of the formula (I) and the formula (Ia) is an amino group substituted with _one C ₁ -C ₆ alkylsulfonyl group, for example, Methanesulfonylamino group, ethanesulfonylamino group, 1-propanesulfonylamino group, 2-propanesulfonylamino group, 1-butanesulfonylamino group, 2-butanesulfonylamino group, 2-methyl-1-propanesulfonylamino group, 2-methyl-2-propanesulfonylamino group, 1-pentanesulfonylamino group, 2-pentanesulfonylamino group, 3-pentanesulfonylamino group, 2-methyl-2-butanesulfonylamino group, 3-methyl-2-butane Sulfonylamino group, 1-hexanesulfonylamino group, 2-hexanesulfonylamino group, -Hexanesulfonylamino group, 2-methyl-1-pentanesulfonylamino group, 3-methyl-1-pentanesulfonylamino group, 2-ethyl-1-butanesulfonylamino group, 2,2-dimethyl-1-butanesulfonylamino group group or it may be a 2,3-dimethyl-1-butane sulfonylamino group, preferably a C ₁ -C ₄ alkylsulfonylamino group, more preferably a methanesulfonylamino group or ethane sulfonylamino group And most preferably a methanesulfonylamino group.

Formula (I) and Formula (Ia) "C ₂ -C ₇ alkylcarbonyl group" in Substituent group α and Substituent group β of the above C ₁ -C ₆ alkyl carbonyl group substituted with group (-CO- For example, methylcarbonyl group, ethylcarbonyl group, 1-propylcarbonyl group, 2-propylcarbonyl group, 1-butylcarbonyl group, 2-butylcarbonyl group, 2-methyl-1-propylcarbonyl group, 2- Methyl-2-propylcarbonyl group, 1-pentylcarbonyl group, 2-pentylcarbonyl group, 3-pentylcarbonyl group, 2-methyl-2-butylcarbonyl group, 3-methyl-2-butylcarbonyl group, 1-hexylcarbonyl Group, 2-hexylcarbonyl group, 3-hexylcarbonyl group, 2-methyl-1-pentylcarbonyl group, 3-methyl-1-penty Carbonyl group, 2-ethyl-1-butyl group, 2,2-dimethyl-1-butyl group, or, can be a 2,3-dimethyl-1-butyl group, preferably a, C ₂ -C _{5 is} an alkylcarbonyl group, more preferably a methylcarbonyl group or an ethylcarbonyl group, and most preferably a methylcarbonyl group.

"C ₂ -C ₇ alkoxycarbonyl group", the C ₁ -C ₆ alkoxy substituted carbonyl group with a group in the substituent group α and Substituent group β of the formula (I) and formula (Ia) (-CO- For example, methoxycarbonyl group, ethoxycarbonyl group, 1-propoxycarbonyl group, 2-propoxycarbonyl group, 1-butoxycarbonyl group, 2-butoxycarbonyl group, 2-methyl-1-propoxycarbonyl group, 2- Methyl-2-propoxycarbonyl group, 1-pentyloxycarbonyl group, 2-pentyloxycarbonyl group, 3-pentyloxycarbonyl group, 2-methyl-2-butoxycarbonyl group, 3-methyl-2-butoxycarbonyl group, 1 -Hexyloxycarbonyl group, 2-hexyloxycarbonyl group, 3-hexyloxycarbonyl group, -Methyl-1-pentyloxycarbonyl group, 3-methyl-1-pentyloxycarbonyl group, 2-ethyl-1-butoxycarbonyl group, 2,2-dimethyl-1-butoxycarbonyl group, or 2,3-dimethyl It can be a -1-butoxycarbonyl group, preferably a C ₂ -C ₅ alkoxycarbonyl group, more preferably a methoxycarbonyl group or an ethoxycarbonyl group, and most preferably a methoxycarbonyl group. .

Formula (I) and formula (Ia) of the "C ₂ -C ₇ alkylaminocarbonyl group" in Substituent group α and Substituent group β, said C ₁ -C ₆ alkylamino carbonyl group substituted with group (- CO-), for example, methylaminocarbonyl group, ethylaminocarbonyl group, 1-propylaminocarbonyl group, 2-propylaminocarbonyl group, 1-butylaminocarbonyl group, 2-butylaminocarbonyl group, 2-methyl- 1-propylaminocarbonyl group, 2-methyl-2-propylaminocarbonyl group, 1-pentylaminocarbonyl group, 2-pentylaminocarbonyl group, 3-pentylaminocarbonyl group, 2-methyl-2-butylaminocarbonyl group, 3-methyl-2-butylaminocarbonyl group, 1-hexylaminocarbonyl group, 2-hexylamino Carbonyl group, 3-hexylaminocarbonyl group, 2-methyl-1-pentylaminocarbonyl group, 3-methyl-1-pentylaminocarbonyl group, 2-ethyl-1-butylaminocarbonyl group, 2,2-dimethyl-1 - butylamino carbonyl group or may be a 2,3-dimethyl-1-butylamino group, preferably a C ₂ -C ₅ alkylaminocarbonyl group, and more preferably, or methylaminocarbonyl group An ethylaminocarbonyl group, most preferably a methylaminocarbonyl group.

The “di (C ₁ -C ₆ alkyl) aminocarbonyl group” in the substituent group α and the substituent group β of the formula (I) and the formula (Ia) is the di (C ₁ -C ₆ alkyl) amino group The alkyl group is a carbonyl group (-CO-) substituted with the same or different, for example, (dimethylamino) carbonyl group, (N-methyl-N-ethylamino) carbonyl group, (methylpropylamino) carbonyl Group [for example, [N- (1-propyl) -N-methylamino] carbonyl group and the like], (diethylamino) carbonyl group, (ethylpropylamino) carbonyl group [for example, [N- (1-propyl) -N- Ethylamino] carbonyl group etc.], (dipropylamino) carbonyl group [e.g. [di (1-propyl) amino] carbonyl group, [di (2-propyl) amino] carbonyl group etc.], [di (1- Til) amino] carbonyl group, [di (2-butyl) amino] carbonyl group, [di (2-methyl-1-propyl) amino] carbonyl group, [di (2-methyl-2-propyl) amino] carbonyl group , [Di (1-pentyl) amino] carbonyl group, [di (2-pentyl) amino] carbonyl group, [di (2-methyl-1-butyl) amino] carbonyl group, [di (3-pentyl) amino] Carbonyl group, [di (1-ethyl-2-propyl) amino] carbonyl group, [di (1-hexyl) amino] carbonyl group, [di (2-hexyl) amino] carbonyl group, [di (3-hexyl) Amino] carbonyl group, [di (2-methyl-1-pentyl) amino] carbonyl group, [di (3-methyl-1-pentyl) amino] carbonyl group, [di (4-methyl-1-pentyl) amino] Carbonyl group, [di (2 Methyl-2-pentyl) amino] carbonyl group, [di (3-methyl-2-pentyl) amino] carbonyl group, [di (4-methyl-2-pentyl) amino] carbonyl group, [di (2,2- [Dimethyl-1-butyl) amino] carbonyl group, [di (3,3-dimethyl-1-butyl) amino] carbonyl group, [di (2,3-dimethyl-1-butyl) amino] carbonyl group, or [ Di (2-ethyl-1-butyl) amino] carbonyl group, preferably a di (C ₁ -C ₄ alkyl) aminocarbonyl group (the alkyl groups being the same or different), and more preferably Is a (dimethylamino) carbonyl group or a (diethylamino) carbonyl group, most preferably a (dimethylamino) carbonyl group.

  The “halogeno group” in the substituent group α and the substituent group β in the formula (I) and the formula (Ia) may be a fluoro group, a chloro group, a bromo group, or an iodo group, preferably a fluoro group, It is a chloro group or a bromo group, more preferably a fluoro group or a chloro group, and most preferably a fluoro group.

The “C ₁ -C ₄ alkylenedioxy group” in the substituent group α and the substituent group β of the formula (I) and the formula (Ia) is an alkylenedioxy group having 1 to 4 carbon atoms, for example, , Methylenedioxy group, ethylene-1,2-dioxy group, 1-methylmethylenedioxy group, propylene-1,3-dioxy group, 1-methylethylene-1,2-dioxy group, 2-methylethylene-1 , 2-dioxy group, 1-ethylmethylenedioxy group, butylene-1,4-dioxy group, 1-methylpropylene-1,3-dioxy group, 2-methylpropylene-1,3-dioxy group, 3-methyl Propylene-1,3-dioxy group, 1-ethylethylene-1,2-dioxy group, 2-ethylethylene-1,2-dioxy group, 1,2-dimethylethylene-1,2-dioxy group, or 1 -Propylme It is a dioxy group, preferably a C ₁ -C ₃ alkylenedioxy group, more preferably a methylenedioxy group or an ethylene-1,2-dioxy group, and most preferably methylene Dioxy group.

When the compound having the general formula (I) or the general formula (Ia) of the present invention has a basic group or an acidic group, it can be converted into a salt by reacting with an acid or a base according to a conventional method. If these salts are used in the treatment of disease, they must be pharmacologically acceptable.

The salt formed with the basic group of the compound having the general formula (I) or the general formula (Ia) of the present invention is preferably, for example, hydrochloride, hydrobromide, hydroiodide, etc. Inorganic acid salts such as hydrohalides; nitrates; perchlorates; sulfates; or phosphates; substituted with fluorine atoms such as methanesulfonate, trifluoromethanesulfonate, ethanesulfonate, etc. Good salts with C ₁ -C ₆ alkane sulfonic acids; salts with C ₆ -C ₁₀ aryl sulfonic acids optionally substituted with C ₁ -C ₄ alkyl such as benzene sulfonate, p-toluene sulfonate, etc. Acetate; malate; fumarate: succinate; citrate; tartrate; oxalate; or organic acid salt such as maleate; or glycine salt, lysine salt, arginine salt, Ornithine, glutamate, asparagus It may be an amino acid salt such as ginrate, and more preferably a hydrohalide salt.

  The salt formed with the acidic group of the compound having the general formula (I) or the general formula (Ia) of the present invention is preferably an alkali metal salt such as sodium salt, potassium salt, lithium salt; Alkaline earth metal salts such as magnesium salts; Aluminum salts; Iron salts; Zinc salts; Copper salts; Nickel salts; Metal salts such as cobalt salts; Inorganic amine salts such as ammonium salts; or t-octylamine salts; Dibenzylamine salt, morpholine salt, glucosamine salt, phenylglycine alkyl ester salt, ethylenediamine salt, N-methylglucamine salt, guanidine salt, diethylamine salt, triethylamine salt, dicyclohexylamine salt, N, N′-dibenzylethylenediamine salt, Chloroprocaine salt, procaine salt, diethanolamine salt, N-benzylphenol Amine salts such as organic amine salts such as netylamine salt, piperazine salt, tetramethylammonium salt, tris (hydroxymethyl) aminomethane salt; or glycine salt, lysine salt, arginine salt, ornithine salt, glutamate salt, aspartate salt And more preferably an alkali metal salt.

  The compound having the general formula (I) or the general formula (Ia) of the present invention or a pharmacologically acceptable salt thereof forms a hydrate by leaving it in the air or adsorbing water during recrystallization. These hydrates are also included in the present invention. Furthermore, although the compounds of the present invention may incorporate other solvents to form solvates, these solvates are also encompassed by the present invention.

  The compound having the general formula (I) or the general formula (Ia) of the present invention or a pharmacologically acceptable salt thereof, and having one or more asymmetric centers, there are optical isomers (including diastereomers). These isomers and mixtures thereof are described in a single formula such as formula (I) or formula (Ia). The present invention encompasses each of these isomers and any mixture thereof (including racemates) in any proportion.

  When geometric isomers exist in the compound having the general formula (I) or the general formula (Ia) of the present invention or a pharmacologically acceptable salt thereof, each of the isomers and a mixture thereof in an arbitrary ratio are all included in the present invention. Is included.

  In the present invention, obesity indicates a state in which the body weight is significantly increased compared to the standard body weight, and complications include lifestyle diseases such as hyperlipidemia, hyperTGemia, diabetes, hypertension, and arteriosclerosis. , Respiratory abnormalities, low back pain, knee osteoarthritis, gout, cholelithiasis and the like. In the present invention, obesity refers to obesity having these complications or those that may cause these complications in the future.

  The compounds having the general formula (I) or the general formula (Ia) of the present invention can be, for example, the compounds shown in Tables 1 and 2, but are not limited to these compounds.

In Tables 1 and 2 below, the following abbreviations are used;
Ac: Acetyl
Azt: Azetidinyl
Bnf: Benzofuranyl
Bni: Benzimidazolyl
Bnt: benzothienyl
Btdz: Benzothiadiazolyl
Btz: benzothiazolyl
Bz: benzyl
cBu: Cyclobutyl
cHp: cycloheptyl
cHx: cyclohexyl
cOc: Cyclooctyl
cPn: cyclopentyl
cPr: Cyclopropyl
Et: ethyl
Etdo: Ethylene-1,2-dioxy
Fur: Frill
Hx: Hexyl
Imd: imidazolyl
Imdd: imidazolidinyl
Imdn: imidazolinyl
Imth: Imidazothiazolyl
Imth [2,1-b]: Imidazo [2,1-b] thiazolyl
Ind: In-drill
Idan: Indanil
Iden: Indenyl
Iox: Isoxazolyl
iBu: 2-methyl-1-propyl
iPr: 2-propyl
Iql: Isoquinolyl
Ith: isothiazolyl
Me: methyl
Mor: Morpholinyl
Mtdo: Methylenedioxy
Nap: Naphthyl
nBu: 1-butyl
nHp: 1-heptyl
nHx: 1-hexyl
nOc: 1-octyl
nPn: 1-pentyl
nPr: 1-propyl
Odp: 2-oxo-1,2-dihydropyridyl
Odz: Oxadiazolyl
Oxz: Oxazolyl
Peac: Perhydroazosinyl
Pean: Perhydroazoninyl
Peap: Perhydroazepinyl
Ph: Phenyl
Pip: Piperidinyl
Pipz: Piperazinyl
Pr: Propyl
Prl: Pyrazolyl
Prld: pyrazolidinyl
Prln: Pyrazolinyl
Prz: Pyrazinyl
Pyd: Pyridazinyl
Pyl: pyrrolyl
Pyln: pyrrolinyl
Pym: pyrimidinyl
Pyr: Pyridyl
Pyrd: Pyrrolidinyl
Qnl: Quinolyl
Qnx: Quinoxalinyl
Qnz: Quinazolinyl
sBu: 2-butyl
Taz: Triazolyl
tBu: 2-methyl-2-propyl
Tdz: Chiadia Zoril
Tet: Tetrazolyl
Thdt: 5-thioxo-4.5-dihydro-1H-1,2,4-triazolyl
Thi: Thienyl
Thm: Thiomorpholinyl
Thz: Thiazolyl
Tmdo: trimethylene-1,3-dioxy
Tpm: 1,4,5,6-tetrahydropyrimidinyl
Tpy: 1,2,3,6-tetrahydropyridyl.

(Table 1)

￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣
Exemplary compounds
Number A¹                    A²                      A^Three
￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣
1-1 nHp 2,3-diMe-Ph 1-Nap
1-2 nOc 2,3-diMe-Ph 1-Nap
1-3 Ph (CH₂)₂                  2,3-diMe-Ph 1-Nap
1-4 (2-MeO-Ph) (CH₂)₂          2,3-diMe-Ph 1-Nap
1-5 (3-MeO-Ph) (CH₂)₂          2,3-diMe-Ph 1-Nap
1-6 PhCH (Me) CH₂              2,3-diMe-Ph 1-Nap
1-7 Ph (CH₂)_Three                 2,3-diMe-Ph 1-Nap
1-8 PhO (CH₂)₂                2,3-diMe-Ph 1-Nap
1-9 PhO (CH₂) CH (Me) 2,3-diMe-Ph 1-Nap
1-10 3-PhO-PhCH₂              2,3-diMe-Ph 1-Nap
1-11 4-PhO-PhCH₂              2,3-diMe-Ph 1-Nap
1-12 cPr 2,3-diMe-Ph 1-Nap
1-13 cBu 2,3-diMe-Ph 1-Nap
1-14 cPn 2,3-diMe-Ph 1-Nap
1-15 cHx 2,3-diMe-Ph 1-Nap
1-16 2-Me-cHx 2,3-diMe-Ph 1-Nap
1-17 cHp 2,3-diMe-Ph 1-Nap
1-18 Ph Ph Ph
1-19 Ph Ph 1-Nap
1-20 Ph 2,3-diMe-Ph 1-Nap
1-21 2-Me-Ph 2,3-diMe-Ph 1-Nap
1-22 3-Me-Ph 2,3-diMe-Ph 1-Nap
1-23 4-Me-Ph 2,3-diMe-Ph 1-Nap
1-24 4-Et-Ph 2,3-diMe-Ph 1-Nap
1-25 4-nPr-Ph 2,3-diMe-Ph 1-Nap
1-26 4-nPr-Ph 2,3-diMe-Ph 8-Qnl
1-27 4-nPr-Ph 2-MeO-3-Pyr 1-Nap
1-28 4-nPr-Ph 2-MeO-3-Pyr 8-Qnl
1-29 4-nBu-Ph 2,3-diMe-Ph 1-Nap
1-30 2-CF_Three-Ph 2,3-diMe-Ph 1-Nap
1-31 3-CF_Three-Ph 2,3-diMe-Ph 1-Nap
1-32 4-CF_Three-Ph 2,3-diMe-Ph 1-Nap
1-33 4-CF_Three-Ph 2,3-diMe-Ph 8-Qnl
1-34 4-CF_Three-Ph 2-MeO-3-Pyr 1-Nap
1-35 4-CF_Three-Ph 2-MeO-3-Pyr 8-Qnl
1-36 4-CH_ThreeCH (OH) -Ph 2,3-diMe-Ph 1-Nap
1-37 4-MeNHSO₂CH₂-Ph 2,3-diMe-Ph 1-Nap
1-38 4- [HON = C (Me)]-Ph 2,3-diMe-Ph 1-Nap
1-39 4- [HON = C (Me)]-Ph 2,3-diMe-Ph 8-Qnl
1-40 4- [HON = C (Me)]-Ph 2-MeO-3-Pyr 1-Nap
1-41 4- [HON = C (Me)]-Ph 2-MeO-3-Pyr 8-Qnl
1-42 4- [MeON = C (Me)]-Ph 2,3-diMe-Ph 1-Nap
1-43 4-cPr-Ph 2,3-diMe-Ph 1-Nap
1-44 4- (HC≡C) -Ph 2,3-diMe-Ph 1-Nap
1-45 4-HO-Ph 3-CF_Three-Ph 1-Nap
1-46 4-HO-Ph 2,3-diMe-Ph 1-Nap
1-47 2-MeO-Ph 2,3-diMe-Ph 1-Nap
1-48 3-MeO-Ph 2,3-diMe-Ph 1-Nap
1-49 4-MeO-Ph 3-CF_Three-Ph Ph
1-50 4-MeO-Ph 3-CF_Three-Ph 1-Nap
1-51 4-MeO-Ph 3-CF_Three-Ph 8-Qnl
1-52 4-MeO-Ph 2,3-diMe-Ph 1-Nap
1-53 4-MeO-Ph 2,3-diMe-Ph 4-Me-1-Nap
1-54 4-MeO-Ph 2,3-diMe-Ph 5-Me-1-Nap
1-55 4-MeO-Ph 2,3-diMe-Ph 4-MeO-1-Nap
1-56 4-MeO-Ph 2,3-diMe-Ph 5-MeO-1-Nap
1-57 4-MeO-Ph 2,3-diMe-Ph 4-MeNH-1-Nap
1-58 4-MeO-Ph 2,3-diMe-Ph 5-MeNH-1-Nap
1-59 4-MeO-Ph 2,3-diMe-Ph 4-Me₂N-1-Nap
1-60 4-MeO-Ph 2,3-diMe-Ph 5-Me₂N-1-Nap
1-61 4-MeO-Ph 2,3-diMe-Ph 4-F-1-Nap
1-62 4-MeO-Ph 2,3-diMe-Ph 5-F-1-Nap
1-63 4-MeO-Ph 2,3-diMe-Ph 4-Cl-1-Nap
1-64 4-MeO-Ph 2,3-diMe-Ph 5-Cl-1-Nap
1-65 4-MeO-Ph 2,3-diMe-Ph 4-Qnl
1-66 4-MeO-Ph 2,3-diMe-Ph 5-Qnl
1-67 4-MeO-Ph 2,3-diMe-Ph 8-Qnl
1-68 4-MeO-Ph 2,3-diMe-Ph 5-Iql
1-69 4-MeO-Ph 2,3-diMe-Ph 8-Iql
1-70 4-MeO-Ph 2,3-diMe-Ph 5-Qnz
1-71 4-MeO-Ph 2,3-diMe-Ph 8-Qnz
1-72 4-MeO-Ph 2,3-diMe-Ph 5-Qnx
1-73 4-MeO-Ph 2,3-diMe-Ph 8-Qnx
1-74 4-MeO-Ph 3-Pyr 1-Nap
1-75 4-MeO-Ph 3-Pyr 8-Qnl
1-76 4-MeO-Ph 2-MeO-3-Pyr 1-Nap
1-77 4-MeO-Ph 2-MeO-3-Pyr 8-Qnl
1-78 4-EtO-Ph nHx 1-Nap
1-79 4-EtO-Ph 2-Et-1-Hx 1-Nap
1-80 4-EtO-Ph nHp 1-Nap
1-81 4-EtO-Ph nOc 1-Nap
1-82 4-EtO-Ph Me₂N (CH₂)_Three                1-Nap
1-83 4-EtO-Ph Me₂N (CH₂) C (Me)₂CH₂         1-Nap
1-84 4-EtO-Ph MeS (CH₂)_Three                 1-Nap
1-85 4-EtO-Ph MeS (CH₂)₂CH (Me) 1-Nap
1-86 4-EtO-Ph PhCH₂                     1-Nap
1-87 4-EtO-Ph (2-Cl-Ph) CH₂              1-Nap
1-88 4-EtO-Ph Ph (CH₂)₂                  1-Nap
1-89 4-EtO-Ph PhCH (Me) CH₂               1-Nap
1-90 4-EtO-Ph (R) -PhCH (Me) CH₂           1-Nap
1-91 4-EtO-Ph (S) -PhCH (Me) CH₂           1-Nap
1-92 4-EtO-Ph (2-MeO-Ph) (CH₂)₂          1-Nap
1-93 4-EtO-Ph (4-MeO-Ph) (CH₂)₂          1-Nap
1-94 4-EtO-Ph Ph (CH₂)_Three                  1-Nap
1-95 4-EtO-Ph Ph (CH₂)₂CH (Me) 1-Nap
1-96 4-EtO-Ph (2-Thi) (CH₂)₂             1-Nap
1-97 4-EtO-Ph (4-Pyr) (CH₂)₂             1-Nap
1-98 4-EtO-Ph (1-Pyrd) (CH₂)₂            1-Nap
1-99 4-EtO-Ph (4-Mor) (CH₂)₂             1-Nap
1-100 4-EtO-Ph PhO (CH₂)₂                 1-Nap
1-101 4-EtO-Ph PhO (CH₂) CH (Me) 1-Nap
1-102 4-EtO-Ph cPr 1-Nap
1-103 4-EtO-Ph cBu 1-Nap
1-104 4-EtO-Ph cPn 1-Nap
1-105 4-EtO-Ph cHx 1-Nap
1-106 4-EtO-Ph 2-Me-cHx 1-Nap
1-107 4-EtO-Ph 4-Me-cHx 1-Nap
1-108 4-EtO-Ph 2,3-diMe-cHx 1-Nap
1-109 4-EtO-Ph Ph 1-Nap
1-110 4-EtO-Ph 2-Me-Ph 1-Nap
1-111 4-EtO-Ph 2-Me-Ph 8-Qnl
1-112 4-EtO-Ph 3-Me-Ph 1-Nap
1-113 4-EtO-Ph 3-Me-Ph 8-Qnl
1-114 4-EtO-Ph 4-Me-Ph 1-Nap
1-115 4-EtO-Ph 4-Me-Ph 8-Qnl
1-116 4-EtO-Ph 3-CF_Three-Ph Ph
1-117 4-EtO-Ph 3-CF_Three-Ph Ph
1-118 4-EtO-Ph 3-CF_Three-Ph 2-Me-Ph
1-119 4-EtO-Ph 3-CF_Three-Ph 3-Me-Ph
1-120 4-EtO-Ph 3-CF_Three-Ph 4-Me-Ph
1-121 4-EtO-Ph 3-CF_Three-Ph 4-Et-Ph
1-122 4-EtO-Ph 3-CF_Three-Ph 4-nPr-Ph
1-123 4-EtO-Ph 3-CF_Three-Ph 4-nBu-Ph
1-124 4-EtO-Ph 3-CF_Three-Ph 4-tBu-Ph
1-125 4-EtO-Ph 3-CF_Three-Ph 3-CF_Three-Ph
1-126 4-EtO-Ph 3-CF_Three-Ph 4-CF_Three-Ph
1-127 4-EtO-Ph 3-CF_Three-Ph 3-MeO-Ph
1-128 4-EtO-Ph 3-CF_Three-Ph 4-MeO-Ph
1-129 4-EtO-Ph 3-CF_Three-Ph 4-EtO-Ph
1-130 4-EtO-Ph 3-CF_Three-Ph 4-nPrO-Ph
1-131 4-EtO-Ph 3-CF_Three-Ph 4-nBuO-Ph
1-132 4-EtO-Ph 3-CF_Three-Ph 4-CF_ThreeO-Ph
1-133 4-EtO-Ph 3-CF_Three-Ph 4-MeSO₂-Ph
1-134 4-EtO-Ph 3-CF_Three-Ph 4-AcNH-Ph
1-135 4-EtO-Ph 3-CF_Three-Ph 2-CN-Ph
1-136 4-EtO-Ph 3-CF_Three-Ph 3-CN-Ph
1-137 4-EtO-Ph 3-CF_Three-Ph 4-CN-Ph
1-138 4-EtO-Ph 3-CF_Three-Ph 3-NO₂-Ph
1-139 4-EtO-Ph 3-CF_Three-Ph 4-NO₂-Ph
1-140 4-EtO-Ph 3-CF_Three-Ph 2-F-Ph
1-141 4-EtO-Ph 3-CF_Three-Ph 3-F-Ph
1-142 4-EtO-Ph 3-CF_Three-Ph 4-F-Ph
1-143 4-EtO-Ph 3-CF_Three-Ph 2-Cl-Ph
1-144 4-EtO-Ph 3-CF_Three-Ph 3-Cl-Ph
1-145 4-EtO-Ph 3-CF_Three-Ph 4-Cl-Ph
1-146 4-EtO-Ph 3-CF_Three-Ph 2-Ph-Ph
1-147 4-EtO-Ph 3-CF_Three-Ph 3-Ph-Ph
1-148 4-EtO-Ph 3-CF_Three-Ph 4-Ph-Ph
1-149 4-EtO-Ph 3-CF_Three-Ph 1-Nap
1-150 4-EtO-Ph 3-CF_Three-Ph 2-Nap
1-151 4-EtO-Ph 3-CF_Three-Ph 4-Me-1-Nap
1-152 4-EtO-Ph 3-CF_Three-Ph 5-Me-1-Nap
1-153 4-EtO-Ph 3-CF_Three-Ph 4-Me₂N-1-Nap
1-154 4-EtO-Ph 3-CF_Three-Ph 5-Me₂N-1-Nap
1-155 4-EtO-Ph 3-CF_Three-Ph 5-Imd
1-156 4-EtO-Ph 3-CF_Three-Ph 2-Me-5-Imd
1-157 4-EtO-Ph 3-CF_Three-Ph 2,3-diMe-5-Imd
1-158 4-EtO-Ph 3-CF_Three-Ph 4-Iox
1-159 4-EtO-Ph 3-CF_Three-Ph 3,5-diMe-4-Iox
1-160 4-EtO-Ph 3-CF_Three-Ph 2-Thi
1-161 4-EtO-Ph 3-CF_Three-Ph 5-Me-2-Thi
1-162 4-EtO-Ph 3-CF_Three-Ph 5-Cl-2-Thi
1-163 4-EtO-Ph 3-CF_Three-Ph 5-Thz
1-164 4-EtO-Ph 3-CF_Three-Ph 4-Me-5-Thz
1-165 4-EtO-Ph 3-CF_Three-Ph 2-AcNH-4-Me-5-Thz
1-166 4-EtO-Ph 3-CF_Three-Ph 2-Bnt
1-167 4-EtO-Ph 3-CF_Three-Ph 3-Me-2-Bnt
1-168 4-EtO-Ph 3-CF_Three-Ph 3-Me-5-Cl-2-Bnt
1-169 4-EtO-Ph 3-CF_Three-Ph 4-Qnl
1-170 4-EtO-Ph 3-CF_Three-Ph 5-Qnl
1-171 4-EtO-Ph 3-CF_Three-Ph 8-Qnl
1-172 4-EtO-Ph 3-CF_Three-Ph 1-Iql
1-173 4-EtO-Ph 3-CF_Three-Ph 4-Iql
1-174 4-EtO-Ph 3-CF_Three-Ph 5-Iql
1-175 4-EtO-Ph 3-CF_Three-Ph 8-Iql
1-176 4-EtO-Ph 3-CF_Three-Ph 5-Qnz
1-177 4-EtO-Ph 3-CF_Three-Ph 8-Qnz
1-178 4-EtO-Ph 3-CF_Three-Ph 5-Qnx
1-179 4-EtO-Ph 3-CF_Three-Ph 8-Qnx
1-180 4-EtO-Ph 3-CF_Three-Ph 5-Imth [2,1-b]
1-181 4-EtO-Ph 3-CF_Three-Ph 6-Cl-5-Imth [2,1-b]
1-182 4-EtO-Ph 3-CF_Three-Ph 4- (1,2,3-Btdz)
1-183 4-EtO-Ph 4-CF_Three-Ph 1-Nap
1-184 4-EtO-Ph 4-HO-Ph 1-Nap
1-185 4-EtO-Ph 2-MeO-Ph 1-Nap
1-186 4-EtO-Ph 2-MeO-Ph 8-Qnl
1-187 4-EtO-Ph 3-MeO-Ph 1-Nap
1-188 4-EtO-Ph 4-MeO-Ph 1-Nap
1-189 4-EtO-Ph 4-EtO-Ph Ph
1-190 4-EtO-Ph 2-CF_ThreeO-Ph 1-Nap
1-191 4-EtO-Ph 3-CF_ThreeO-Ph 1-Nap
1-192 4-EtO-Ph 4-CF_ThreeO-Ph 1-Nap
1-193 4-EtO-Ph 4-HCOO-Ph 1-Nap
1-194 4-EtO-Ph 4-MeCOO-Ph 1-Nap
1-195 4-EtO-Ph 4-MeS-Ph 1-Nap
1-196 4-EtO-Ph 4-MeSO-Ph 1-Nap
1-197 4-EtO-Ph 4-MeSO₂-Ph 1-Nap
1-198 4-EtO-Ph 4-H₂N-Ph 1-Nap
1-199 4-EtO-Ph 4-MeNH-Ph 1-Nap
1-200 4-EtO-Ph 4-Me₂N-Ph 1-Nap
1-201 4-EtO-Ph 4-HCONH-Ph 1-Nap
1-202 4-EtO-Ph 4-MeCONH-Ph 1-Nap
1-203 4-EtO-Ph 4-MeOCONH-Ph 1-Nap
1-204 4-EtO-Ph 4-HCO-Ph 1-Nap
1-205 4-EtO-Ph 2-Ac-Ph 1-Nap
1-206 4-EtO-Ph 3-Ac-Ph 1-Nap
1-207 4-EtO-Ph 4-Ac-Ph 1-Nap
1-208 4-EtO-Ph 4-HOCO-Ph 1-Nap
1-209 4-EtO-Ph 4-MeOCO-Ph 1-Nap
1-210 4-EtO-Ph 2-EtOCO-Ph 1-Nap
1-211 4-EtO-Ph 3-EtOCO-Ph 1-Nap
1-212 4-EtO-Ph 4-EtOCO-Ph 1-Nap
1-213 4-EtO-Ph 4-H₂NCO-Ph 1-Nap
1-214 4-EtO-Ph 4-MeNHCO-Ph 1-Nap
1-215 4-EtO-Ph 4-Me₂NCO-Ph 1-Nap
1-216 4-EtO-Ph 3-CN-Ph 1-Nap
1-217 4-EtO-Ph 4-CN-Ph 1-Nap
1-218 4-EtO-Ph 3-NO₂-Ph 1-Nap
1-219 4-EtO-Ph 4-NO₂-Ph 1-Nap
1-220 4-EtO-Ph 2-F-Ph 1-Nap
1-221 4-EtO-Ph 3-F-Ph 1-Nap
1-222 4-EtO-Ph 4-F-Ph 1-Nap
1-223 4-EtO-Ph 2-Cl-Ph 1-Nap
1-224 4-EtO-Ph 2-Cl-Ph 8-Qnl
1-225 4-EtO-Ph 3-Cl-Ph 1-Nap
1-226 4-EtO-Ph 4-Cl-Ph 1-Nap
1-227 4-EtO-Ph 4-HOCOCH₂-Ph 1-Nap
1-228 4-EtO-Ph 4-MeOCOCH₂-Ph 1-Nap
1-229 4-EtO-Ph 3,4-Mtdo-Ph 1-Nap
1-230 4-EtO-Ph 3,4-Tmdo-Ph 1-Nap
1-231 4-EtO-Ph 2,3-diMe-Ph Bn
1-232 4-EtO-Ph 2,3-diMe-Ph Ph (CH₂)₂
1-233 4-EtO-Ph 2,3-diMe-Ph Ph (CH₂)_Three
1-234 4-EtO-Ph 2,3-diMe-Ph Ph
1-235 4-EtO-Ph 2,3-diMe-Ph 4-CF_Three-Ph
1-236 4-EtO-Ph 2,3-diMe-Ph 4-MeO-Ph
1-237 4-EtO-Ph 2,3-diMe-Ph 4-CF_ThreeO-Ph
1-238 4-EtO-Ph 2,3-diMe-Ph 4-MeS-Ph
1-239 4-EtO-Ph 2,3-diMe-Ph 4-H₂N-Ph
1-240 4-EtO-Ph 2,3-diMe-Ph 4-MeNH-Ph
1-241 4-EtO-Ph 2,3-diMe-Ph 4-Me₂N-Ph
1-242 4-EtO-Ph 2,3-diMe-Ph 4-HCO-Ph
1-243 4-EtO-Ph 2,3-diMe-Ph 4-Ac-Ph
1-244 4-EtO-Ph 2,3-diMe-Ph 4-MeOCO-Ph
1-245 4-EtO-Ph 2,3-diMe-Ph 4-H₂NCO-Ph
1-246 4-EtO-Ph 2,3-diMe-Ph 4-MeNHCO-Ph
1-247 4-EtO-Ph 2,3-diMe-Ph 4-Me₂NCO-Ph
1-248 4-EtO-Ph 2,3-diMe-Ph 4-CN-Ph
1-249 4-EtO-Ph 2,3-diMe-Ph 2-NO₂-Ph
1-250 4-EtO-Ph 2,3-diMe-Ph 4-NO₂-Ph
1-251 4-EtO-Ph 2,3-diMe-Ph 4-F-Ph
1-252 4-EtO-Ph 2,3-diMe-Ph 4-Cl-Ph
1-253 4-EtO-Ph 2,3-diMe-Ph 3,4-Mtdo-Ph
1-254 4-EtO-Ph 2,3-diMe-Ph 4-Me-2-MeO-Ph
1-255 4-EtO-Ph 2,3-diMe-Ph 2-Me-5-NO₂-Ph
1-256 4-EtO-Ph 2,3-diMe-Ph 4-Me-3-NO₂-Ph
1-257 4-EtO-Ph 2,3-diMe-Ph 2-Me-5-F-Ph
1-258 4-EtO-Ph 2,3-diMe-Ph 2-Me-3-Cl-Ph
1-259 4-EtO-Ph 2,3-diMe-Ph 2-Me-6-Cl-Ph
1-260 4-EtO-Ph 2,3-diMe-Ph 2-Me-4-Br-Ph
1-261 4-EtO-Ph 2,3-diMe-Ph 2-Et-4-Br-Ph
1-262 4-EtO-Ph 2,3-diMe-Ph 3,5-di (CF_Three) -Ph
1-263 4-EtO-Ph 2,3-diMe-Ph 4-CF_Three-2-Cl-Ph
1-264 4-EtO-Ph 2,3-diMe-Ph 2,5-diMeO-Ph
1-265 4-EtO-Ph 2,3-diMe-Ph 3,4-diMeO-Ph
1-266 4-EtO-Ph 2,3-diMe-Ph 4-MeO-2-NO₂-Ph
1-267 4-EtO-Ph 2,3-diMe-Ph 2-MeO-5-Cl-Ph
1-268 4-EtO-Ph 2,3-diMe-Ph 2-MeO-5-Br-Ph
1-269 4-EtO-Ph 2,3-diMe-Ph 4-AcNH-3-Cl-Ph
1-270 4-EtO-Ph 2,3-diMe-Ph 2,3-diF-Ph
1-271 4-EtO-Ph 2,3-diMe-Ph 2,4-diF-Ph
1-272 4-EtO-Ph 2,3-diMe-Ph 2,5-diF-Ph
1-273 4-EtO-Ph 2,3-diMe-Ph 2,6-diF-Ph
1-274 4-EtO-Ph 2,3-diMe-Ph 3,4-diF-Ph
1-275 4-EtO-Ph 2,3-diMe-Ph 3,5-diF-Ph
1-276 4-EtO-Ph 2,3-diMe-Ph 4-F-2-Cl-Ph
1-277 4-EtO-Ph 2,3-diMe-Ph 4-F-3-Cl-Ph
1-278 4-EtO-Ph 2,3-diMe-Ph 2,3-diCl-Ph
1-279 4-EtO-Ph 2,3-diMe-Ph 2,4-diCl-Ph
1-280 4-EtO-Ph 2,3-diMe-Ph 2,5-diCl-Ph
1-281 4-EtO-Ph 2,3-diMe-Ph 2,6-diCl-Ph
1-282 4-EtO-Ph 2,3-diMe-Ph 3,4-diCl-Ph
1-283 4-EtO-Ph 2,3-diMe-Ph 3,5-diCl-Ph
1-284 4-EtO-Ph 2,3-diMe-Ph 2,4,6-triMe-Ph
1-285 4-EtO-Ph 2,3-diMe-Ph 2,5-diMe-4-Cl-Ph
1-286 4-EtO-Ph 2,3-diMe-Ph 2-Me-5-F-3-Cl-Ph
1-287 4-EtO-Ph 2,3-diMe-Ph 5-Me-2.4-diCl-Ph
1-288 4-EtO-Ph 2,3-diMe-Ph 2,4,6-tri (iPr) -Ph
1-289 4-EtO-Ph 2,3-diMe-Ph 2,3,5,6-tetraMe-Ph
1-290 4-EtO-Ph 2,3-diMe-Ph 4-Ph-Ph
1-291 4-EtO-Ph 2,3-diMe-Ph 3- (4-CF_Three-Ph) -Ph
1-292 4-EtO-Ph 2,3-diMe-Ph 4- (4-CF_Three-Ph) -Ph
1-293 4-EtO-Ph 2,3-diMe-Ph 3- (4-F-Ph) -Ph
1-294 4-EtO-Ph 2,3-diMe-Ph 4- (4-F-Ph) -Ph
1-295 4-EtO-Ph 2,3-diMe-Ph 3- (4-Cl-Ph) -Ph
1-296 4-EtO-Ph 2,3-diMe-Ph 4- (1-Prl) -Ph
1-297 4-EtO-Ph 2,3-diMe-Ph 4- (1-Imd) -Ph
1-298 4-EtO-Ph 2,3-diMe-Ph 4- (5-Oxz) -Ph
1-299 4-EtO-Ph 2,3-diMe-Ph 4- (5-Thz) -Ph
1-300 4-EtO-Ph 2,3-diMe-Ph 3- [2- (1,3,4-Odz)]-Ph
1-301 4-EtO-Ph 2,3-diMe-Ph 3- [5-Me-2- (1,3,4-Odz)]-Ph
1-302 4-EtO-Ph 2,3-diMe-Ph 3- (4-Pym) -Ph
1-303 4-EtO-Ph 2,3-diMe-Ph 3- (2-Me-4-Pym) -Ph
1-304 4-EtO-Ph 2,3-diMe-Ph 1-Nap
1-305 4-EtO-Ph 2,3-diMe-Ph 3-Me-1-Nap
1-306 4-EtO-Ph 2,3-diMe-Ph 4-Me-1-Nap
1-307 4-EtO-Ph 2,3-diMe-Ph 5-Me-1-Nap
1-308 4-EtO-Ph 2,3-diMe-Ph 4-MeO-1-Nap
1-309 4-EtO-Ph 2,3-diMe-Ph 5-MeO-1-Nap
1-310 4-EtO-Ph 2,3-diMe-Ph 4-MeNH-1-Nap
1-311 4-EtO-Ph 2,3-diMe-Ph 5-MeNH-1-Nap
1-312 4-EtO-Ph 2,3-diMe-Ph 4-Me₂N-1-Nap
1-313 4-EtO-Ph 2,3-diMe-Ph 5-Me₂N-1-Nap
1-314 4-EtO-Ph 2,3-diMe-Ph 4-F-1-Nap
1-315 4-EtO-Ph 2,3-diMe-Ph 5-F-1-Nap
1-316 4-EtO-Ph 2,3-diMe-Ph 4-Cl-1-Nap
1-317 4-EtO-Ph 2,3-diMe-Ph 5-Cl-1-Nap
1-318 4-EtO-Ph 2,3-diMe-Ph 3-Pyr
1-319 4-EtO-Ph 2,3-diMe-Ph 5-Br-6-Cl-3-Pyr
1-320 4-EtO-Ph 2,3-diMe-Ph 5-Ph-2-Thi
1-321 4-EtO-Ph 2,3-diMe-Ph 5- (2-Pyr) -2-Thi
1-322 4-EtO-Ph 2,3-diMe-Ph 5- (5-Prl) -2-Thi
1-323 4-EtO-Ph 2,3-diMe-Ph 5- (1-Me-3-CF_Three-5-Prl) -2-Thi
1-324 4-EtO-Ph 2,3-diMe-Ph 5- (4-Pym) -2-Thi
1-325 4-EtO-Ph 2,3-diMe-Ph 5- (2-MeS-4-Pym) -2-Thi
1-326 4-EtO-Ph 2,3-diMe-Ph 5- (5-Oxz) -2-Thi
1-327 4-EtO-Ph 2,3-diMe-Ph 5- (3-Iox) -2-Thi
1-328 4-EtO-Ph 2,3-diMe-Ph 5- (5-CF_Three-3-Iox) -2-Thi
1-329 4-EtO-Ph 2,3-diMe-Ph 5- (5-Thz) -2-Thi
1-330 4-EtO-Ph 2,3-diMe-Ph 5- [3- (1,2,4-Odz)]-2-Thi
1-331 4-EtO-Ph 2,3-diMe-Ph 5- [5-MeOCO-3- (1,2,4-Odz)]-2-Thi
1-332 4-EtO-Ph 2,3-diMe-Ph 5- [5-EtOCO-3- (1,2,4-Odz)]-2-Thi
1-333 4-EtO-Ph 2,3-diMe-Ph 5- [5-EtOCO-3- (1,2,4-Tdz)]-2-Thi
1-334 4-EtO-Ph 2,3-diMe-Ph 6- (4-Mor) -3-Pyr
1-335 4-EtO-Ph 2,3-diMe-Ph 4-Qnl
1-336 4-EtO-Ph 2,3-diMe-Ph 5-Qnl
1-337 4-EtO-Ph 2,3-diMe-Ph 8-Qnl
1-338 4-EtO-Ph 2,3-diMe-Ph 3-Me-8-Qnl
1-339 4-EtO-Ph 2,3-diMe-Ph 4-Me-8-Qnl
1-340 4-EtO-Ph 2,3-diMe-Ph 5-Me-8-Qnl
1-341 4-EtO-Ph 2,3-diMe-Ph 4-MeO-8-Qnl
1-342 4-EtO-Ph 2,3-diMe-Ph 5-MeO-8-Qnl
1-343 4-EtO-Ph 2,3-diMe-Ph 4-MeNH-8-Qnl
1-344 4-EtO-Ph 2,3-diMe-Ph 5-MeNH-8-Qnl
1-345 4-EtO-Ph 2,3-diMe-Ph 4-Me₂N-8-Qnl
1-346 4-EtO-Ph 2,3-diMe-Ph 5-Me₂N-8-Qnl
1-347 4-EtO-Ph 2,3-diMe-Ph 4-F-8-Qnl
1-348 4-EtO-Ph 2,3-diMe-Ph 5-F-8-Qnl
1-349 4-EtO-Ph 2,3-diMe-Ph 4-Cl-8-Qnl
1-350 4-EtO-Ph 2,3-diMe-Ph 5-Cl-8-Qnl
1-351 4-EtO-Ph 2,3-diMe-Ph 5-Iql
1-352 4-EtO-Ph 2,3-diMe-Ph 8-Iql
1-353 4-EtO-Ph 2,3-diMe-Ph 5-Qnz
1-354 4-EtO-Ph 2,3-diMe-Ph 8-Qnz
1-355 4-EtO-Ph 2,3-diMe-Ph 5-Qnx
1-356 4-EtO-Ph 2,3-diMe-Ph 8-Qnx
1-357 4-EtO-Ph 2,4-diMe-Ph 1-Nap
1-358 4-EtO-Ph 2,4-diMe-Ph 8-Qnl
1-359 4-EtO-Ph 2,5-diMe-Ph 1-Nap
1-360 4-EtO-Ph 2,5-diMe-Ph 8-Qnl
1-361 4-EtO-Ph 2,6-diMe-Ph 1-Nap
1-362 4-EtO-Ph 2,6-diMe-Ph 8-Qnl
1-363 4-EtO-Ph 3,4-diMe-Ph 1-Nap
1-364 4-EtO-Ph 3,4-diMe-Ph 8-Qnl
1-365 4-EtO-Ph 3,5-diMe-Ph 1-Nap
1-366 4-EtO-Ph 3,5-diMe-Ph 8-Qnl
1-367 4-EtO-Ph 2-Me-3-CF_Three-Ph 1-Nap
1-368 4-EtO-Ph 4-Me-3-CF_Three-Ph 1-Nap
1-369 4-EtO-Ph 5-Me-3-CF_Three-Ph 1-Nap
1-370 4-EtO-Ph 2-Me-5-CF_Three-Ph 1-Nap
1-371 4-EtO-Ph 3-CF_Three-4-MeO-Ph 1-Nap
1-372 4-EtO-Ph 3-CF_Three-5-MeO-Ph 1-Nap
1-373 4-EtO-Ph 5-CF_Three-2-MeO-Ph 1-Nap
1-374 4-EtO-Ph 3-CF_Three-4-F-Ph 1-Nap
1-375 4-EtO-Ph 2,3-diMeO-Ph 1-Nap
1-376 4-EtO-Ph 2,4-diMeO-Ph 1-Nap
1-377 4-EtO-Ph 2,5-diMeO-Ph 1-Nap
1-378 4-EtO-Ph 2,6-diMeO-Ph 1-Nap
1-379 4-EtO-Ph 3,4-diMeO-Ph 1-Nap
1-380 4-EtO-Ph 3,4-diMeO-Ph 8-Qnl
1-381 4-EtO-Ph 3,5-diMeO-Ph 1-Nap
1-382 4-EtO-Ph 3,4-diF-Ph 1-Nap
1-383 4-EtO-Ph 3,5-diF-Ph 1-Nap
1-384 4-EtO-Ph 3,4-diCl-Ph 1-Nap
1-385 4-EtO-Ph 3,5-diCl-Ph 1-Nap
1-386 4-EtO-Ph 2-Ph-Ph 1-Nap
1-387 4-EtO-Ph 3-Ph-Ph 1-Nap
1-388 4-EtO-Ph 4-Ph-Ph 1-Nap
1-389 4-EtO-Ph 3- (3-Prl) -Ph 1-Nap
1-390 4-EtO-Ph 4- (3-Prl) -Ph 1-Nap
1-391 4-EtO-Ph 3- (1-Imd) -Ph 1-Nap
1-392 4-EtO-Ph 4- (1-Imd) -Ph 1-Nap
1-393 4-EtO-Ph 3- (2-Imd) -Ph 1-Nap
1-394 4-EtO-Ph 4- (2-Imd) -Ph 1-Nap
1-395 4-EtO-Ph 3- (2-Oxz) -Ph 1-Nap
1-396 4-EtO-Ph 3- (5-Oxz) -Ph 1-Nap
1-397 4-EtO-Ph 4- (2-Oxz) -Ph 1-Nap
1-398 4-EtO-Ph 3- (2-Thz) -Ph 1-Nap
1-399 4-EtO-Ph 4- (2-Thz) -Ph 1-Nap
1-400 4-EtO-Ph 4- (4-Pip) -Ph 1-Nap
1-401 4-EtO-Ph 4- (4-Pipz) -Ph 1-Nap
1-402 4-EtO-Ph 4- (4-Mor) -Ph 1-Nap
1-403 4-EtO-Ph 4- (4-Thm) -Ph 1-Nap
1-404 4-EtO-Ph 1-Nap 1-Nap
1-405 4-EtO-Ph 2-Nap 1-Nap
1-406 4-EtO-Ph 1-Idan 1-Nap
1-407 4-EtO-Ph 2-Idan 1-Nap
1-408 4-EtO-Ph 1-Iden 1-Nap
1-409 4-EtO-Ph 2-Iden 1-Nap
1-410 4-EtO-Ph 3-Thi 1-Nap
1-411 4-EtO-Ph 2-MeOCO-3-Thi 1-Nap
1-412 4-EtO-Ph 5-Prl 1-Nap
1-413 4-EtO-Ph 1-Me-5-Prl 1-Nap
1-414 4-EtO-Ph 1,3-diMe-5-Prl 1-Nap
1-415 4-EtO-Ph 1-Me-4-Br-3-Prl 1-Nap
1-416 4-EtO-Ph 2-Imd 1-Nap
1-417 4-EtO-Ph 5-Imd 1-Nap
1-418 4-EtO-Ph 2-Oxz 1-Nap
1-419 4-EtO-Ph 3-Iox 1-Nap
1-420 4-EtO-Ph 5-Me-3-Iox 1-Nap
1-421 4-EtO-Ph 5-Me-4-Br-3-Iox 1-Nap
1-422 4-EtO-Ph 5-tBu-3-Iox 1-Nap
1-423 4-EtO-Ph 2-Thz 1-Nap
1-424 4-EtO-Ph 4-Me-2-Thz 1-Nap
1-425 4-EtO-Ph 5-Me-2-Thz 1-Nap
1-426 4-EtO-Ph 4- (EtOCOCH₂) -2-Thz 1-Nap
1-427 4-EtO-Ph 4,5-diMe-2-Thz 1-Nap
1-428 4-EtO-Ph 4-Me-5-Ac-2-Thz 1-Nap
1-429 4-EtO-Ph 2- (1,3,4-Taz) 1-Nap
1-430 4-EtO-Ph 2- (1,3,4-Tdz) 1-Nap
1-431 4-EtO-Ph 5-tBu-2- (1,3,4-Tdz) 1-Nap
1-432 4-EtO-Ph 5-cPr-2- (1,3,4-Tdz) 1-Nap
1-433 4-EtO-Ph 2-Pyr 1-Nap
1-434 4-EtO-Ph 3-Pyr 1-Nap
1-435 4-EtO-Ph 4-Pyr 1-Nap
1-436 4-EtO-Ph 4-Me-2-Pyr 1-Nap
1-437 4-EtO-Ph 5-Me-2-Pyr 1-Nap
1-438 4-EtO-Ph 6-Me-2-Pyr 1-Nap
1-439 4-EtO-Ph 2-Me-3-Pyr 1-Nap
1-440 4-EtO-Ph 5-Me-3-Pyr 1-Nap
1-441 4-EtO-Ph 6-Me-3-Pyr 1-Nap
1-442 4-EtO-Ph 2-MeO-3-Pyr 1-Nap
1-443 4-EtO-Ph 2-MeO-3-Pyr 4-Me-1-Nap
1-444 4-EtO-Ph 2-MeO-3-Pyr 5-Me-1-Nap
1-445 4-EtO-Ph 2-MeO-3-Pyr 4-MeO-1-Nap
1-446 4-EtO-Ph 2-MeO-3-Pyr 5-MeO-1-Nap
1-447 4-EtO-Ph 2-MeO-3-Pyr 4-MeNH-1-Nap
1-448 4-EtO-Ph 2-MeO-3-Pyr 5-MeNH-1-Nap
1-449 4-EtO-Ph 2-MeO-3-Pyr 4-Me₂N-1-Nap
1-450 4-EtO-Ph 2-MeO-3-Pyr 5-Me₂N-1-Nap
1-451 4-EtO-Ph 2-MeO-3-Pyr 4-F-1-Nap
1-452 4-EtO-Ph 2-MeO-3-Pyr 5-F-1-Nap
1-453 4-EtO-Ph 2-MeO-3-Pyr 4-Cl-1-Nap
1-454 4-EtO-Ph 2-MeO-3-Pyr 5-Cl-1-Nap
1-455 4-EtO-Ph 2-MeO-3-Pyr 4-Qnl
1-456 4-EtO-Ph 2-MeO-3-Pyr 5-Qnl
1-457 4-EtO-Ph 2-MeO-3-Pyr 8-Qnl
1-458 4-EtO-Ph 2-MeO-3-Pyr 4-Me-8-Qnl
1-459 4-EtO-Ph 2-MeO-3-Pyr 5-Me-8-Qnl
1-460 4-EtO-Ph 2-MeO-3-Pyr 4-MeO-8-Qnl
1-461 4-EtO-Ph 2-MeO-3-Pyr 5-MeO-8-Qnl
1-462 4-EtO-Ph 2-MeO-3-Pyr 4-MeNH-8-Qnl
1-463 4-EtO-Ph 2-MeO-3-Pyr 5-MeNH-8-Qnl
1-464 4-EtO-Ph 2-MeO-3-Pyr 4-Me₂N-8-Qnl
1-465 4-EtO-Ph 2-MeO-3-Pyr 5-Me₂N-8-Qnl
1-466 4-EtO-Ph 2-MeO-3-Pyr 4-F-8-Qnl
1-467 4-EtO-Ph 2-MeO-3-Pyr 5-F-8-Qnl
1-468 4-EtO-Ph 2-MeO-3-Pyr 4-Cl-8-Qnl
1-469 4-EtO-Ph 2-MeO-3-Pyr 5-Cl-8-Qnl
1-470 4-EtO-Ph 2-MeO-3-Pyr 5-Qnz
1-471 4-EtO-Ph 2-MeO-3-Pyr 8-Qnz
1-472 4-EtO-Ph 2-MeO-3-Pyr 5-Qnx
1-473 4-EtO-Ph 2-MeO-3-Pyr 8-Qnx
1-474 4-EtO-Ph 6-MeO-3-Pyr 1-Nap
1-475 4-EtO-Ph 2,6-diMeO-3-Pyr 1-Nap
1-476 4-EtO-Ph 4-Pip 1-Nap
1-477 4-EtO-Ph 1-EtOCO-4-Pip 1-Nap
1-478 4-EtO-Ph 1-Pipz 1-Nap
1-479 4-EtO-Ph 4-Mor 1-Nap
1-480 4-EtO-Ph 4-Thm 1-Nap
1-481 4-EtO-Ph 3-Ph-5-Prl 1-Nap
1-482 4-EtO-Ph 1-Me-3-Ph-5-Prl 1-Nap
1-483 4-EtO-Ph 5-Ph-2-Imd 1-Nap
1-484 4-EtO-Ph 2-Ph-5-Imd 1-Nap
1-485 4-EtO-Ph 5-Ph-2-Thi 1-Nap
1-486 4-EtO-Ph 5-Ph-2-Thz 1-Nap
1-487 4-EtO-Ph 5-Ph-2-Pyr 1-Nap
1-488 4-EtO-Ph 5- (1-Prl) -5-Prl 1-Nap
1-489 4-EtO-Ph 5- (1-Imd) -5-Prl 1-Nap
1-490 4-EtO-Ph 5- (2-Thi) -5-Prl 1-Nap
1-491 4-EtO-Ph 5- (2-Thz) -5-Prl 1-Nap
1-492 4-EtO-Ph 5- (2-Pyr) -5-Prl 1-Nap
1-493 4-EtO-Ph 5- (4-Pip) -5-Prl 1-Nap
1-494 4-EtO-Ph 5- (4-Mor) -5-Prl 1-Nap
1-495 4-EtO-Ph 5- (1-Prl) -2-Imd 1-Nap
1-496 4-EtO-Ph 5- (1-Imd) -2-Imd 1-Nap
1-497 4-EtO-Ph 5- (2-Thi) -2-Imd 1-Nap
1-498 4-EtO-Ph 5- (2-Thz) -2-Imd 1-Nap
1-499 4-EtO-Ph 5- (2-Pyr) -2-Imd 1-Nap
1-500 4-EtO-Ph 5- (4-Pip) -2-Imd 1-Nap
1-501 4-EtO-Ph 5- (1-Prl) -2-Thi 1-Nap
1-502 4-EtO-Ph 5- (1-Imd) -2-Thi 1-Nap
1-503 4-EtO-Ph 5- (2-Thi) -2-Thi 1-Nap
1-504 4-EtO-Ph 5- (2-Thz) -2-Thi 1-Nap
1-505 4-EtO-Ph 5- (2-Pyr) -2-Thi 1-Nap
1-506 4-EtO-Ph 5- (4-Pip) -2-Thi 1-Nap
1-507 4-EtO-Ph 5- (4-Mor) -2-Thi 1-Nap
1-508 4-EtO-Ph 5- (1-Prl) -2-Thz 1-Nap
1-509 4-EtO-Ph 5- (1-Imd) -2-Thz 1-Nap
1-510 4-EtO-Ph 5- (2-Thi) -2-Thz 1-Nap
1-511 4-EtO-Ph 5- (2-Thz) -2-Thz 1-Nap
1-512 4-EtO-Ph 5- (2-Pyr) -2-Thz 1-Nap
1-513 4-EtO-Ph 5- (4-Pip) -2-Thz 1-Nap
1-514 4-EtO-Ph 5- (4-Mor) -2-Thz 1-Nap
1-515 4-EtO-Ph 5- (1-Prl) -2-Pyr 1-Nap
1-516 4-EtO-Ph 5- (1-Imd) -2-Pyr 1-Nap
1-517 4-EtO-Ph 5- (2-Thi) -2-Pyr 1-Nap
1-518 4-EtO-Ph 5- (2-Thz) -2-Pyr 1-Nap
1-519 4-EtO-Ph 5- (2-Pyr) -2-Pyr 1-Nap
1-520 4-EtO-Ph 5- (4-Pip) -2-Pyr 1-Nap
1-521 4-EtO-Ph 5- (4-Mor) -2-Pyr 1-Nap
1-522 4-EtO-Ph 6- (4-Mor) -3-Pyd 1-Nap
1-523 4-EtO-Ph 2-Btz 1-Nap
1-524 4-EtO-Ph 6-MeO-2-Btz 1-Nap
1-525 4-EtO-Ph 3-Qnl 1-Nap
1-526 4-EtO-Ph 6-Qnl 1-Nap
1-527 4-EtO-Ph 8-Qnl 1-Nap
1-528 2-nPrO-Ph 2,3-diMe-Ph 1-Nap
1-529 3-nPrO-Ph 2,3-diMe-Ph 1-Nap
1-530 4-nPrO-Ph 3-CF_Three-Ph Ph
1-531 4-nPrO-Ph 3-CF_Three-Ph 1-Nap
1-532 4-nPrO-Ph 3-CF_Three-Ph 8-Qnl
1-533 4-nPrO-Ph 2,3-diMe-Ph 1-Nap
1-534 4-nPrO-Ph 2,3-diMe-Ph 4-Me-1-Nap
1-535 4-nPrO-Ph 2,3-diMe-Ph 5-Me-1-Nap
1-536 4-nPrO-Ph 2,3-diMe-Ph 4-MeO-1-Nap
1-537 4-nPrO-Ph 2,3-diMe-Ph 5-MeO-1-Nap
1-538 4-nPrO-Ph 2,3-diMe-Ph 4-MeNH-1-Nap
1-539 4-nPrO-Ph 2,3-diMe-Ph 5-MeNH-1-Nap
1-540 4-nPrO-Ph 2,3-diMe-Ph 4-Me₂N-1-Nap
1-541 4-nPrO-Ph 2,3-diMe-Ph 5-Me₂N-1-Nap
1-542 4-nPrO-Ph 2,3-diMe-Ph 4-F-1-Nap
1-543 4-nPrO-Ph 2,3-diMe-Ph 5-F-1-Nap
1-544 4-nPrO-Ph 2,3-diMe-Ph 4-Cl-1-Nap
1-545 4-nPrO-Ph 2,3-diMe-Ph 5-Cl-1-Nap
1-546 4-nPrO-Ph 2,3-diMe-Ph 4-Qnl
1-547 4-nPrO-Ph 2,3-diMe-Ph 5-Qnl
1-548 4-nPrO-Ph 2,3-diMe-Ph 8-Qnl
1-549 4-nPrO-Ph 2,3-diMe-Ph 5-Iql
1-550 4-nPrO-Ph 2,3-diMe-Ph 8-Iql
1-551 4-nPrO-Ph 2,3-diMe-Ph 5-Qnz
1-552 4-nPrO-Ph 2,3-diMe-Ph 8-Qnz
1-553 4-nPrO-Ph 2,3-diMe-Ph 5-Qnx
1-554 4-nPrO-Ph 2,3-diMe-Ph 8-Qnx
1-555 4-nPrO-Ph 3-Pyr 1-Nap
1-556 4-nPrO-Ph 3-Pyr 8-Qnl
1-557 4-nPrO-Ph 2-MeO-3-Pyr 1-Nap
1-558 4-nPrO-Ph 2-MeO-3-Pyr 8-Qnl
1-559 4-nBuO-Ph 2,3-diMe-Ph 1-Nap
1-560 3-CF_ThreeO-Ph 2,3-diMe-Ph 1-Nap
1-561 4-CF_ThreeO-Ph 2,3-diMe-Ph 1-Nap
1-562 4-CF_ThreeO-Ph 2,3-diMe-Ph 8-Qnl
1-563 4-CF_ThreeO-Ph 2-MeO-3-Pyr 1-Nap
1-564 4-CF_ThreeO-Ph 2-MeO-3-Pyr 8-Qnl
1-565 4-HCOO-Ph 2,3-diMe-Ph 1-Nap
1-566 4-MeCOO-Ph 2,3-diMe-Ph 1-Nap
1-567 4-MeS-Ph 3-CF_Three-Ph 1-Nap
1-568 4-MeS-Ph 3-CF_Three-Ph 8-Qnl
1-569 4-MeS-Ph 2,3-diMe-Ph 1-Nap
1-570 4-MeS-Ph 2,3-diMe-Ph 8-Qnl
1-571 4-MeS-Ph 3-Pyr 1-Nap
1-572 4-MeS-Ph 3-Pyr 8-Qnl
1-573 4-MeS-Ph 2-MeO-3-Pyr 1-Nap
1-574 4-MeS-Ph 2-MeO-3-Pyr 8-Qnl
1-575 4-MeSO-Ph 2,3-diMe-Ph 1-Nap
1-576 4-MeSO₂-Ph 2,3-diMe-Ph 1-Nap
1-577 4-H₂NSO₂-Ph 2,3-diMe-Ph 1-Nap
1-578 4-MeNHSO₂-Ph 2,3-diMe-Ph 1-Nap
1-579 4-H₂N-Ph 2,3-diMe-Ph 1-Nap
1-580 4-MeNH-Ph 2,3-diMe-Ph 1-Nap
1-581 4-Me₂N-Ph 3-CF_Three-Ph 1-Nap
1-582 4-Me₂N-Ph 3-CF_Three-Ph 8-Qnl
1-583 4-Me₂N-Ph 2,3-diMe-Ph 1-Nap
1-584 4-Me₂N-Ph 2,3-diMe-Ph 8-Qnl
1-585 4-Me₂N-Ph 3-Pyr 1-Nap
1-586 4-Me₂N-Ph 3-Pyr 8-Qnl
1-587 4-Me₂N-Ph 2-MeO-3-Pyr 1-Nap
1-588 4-Me₂N-Ph 2-MeO-3-Pyr 8-Qnl
1-589 4-Et₂N-Ph 2,3-diMe-Ph 1-Nap
1-590 4-HCONH-Ph 2,3-diMe-Ph 1-Nap
1-591 4-AcNH-Ph 2,3-diMe-Ph 1-Nap
1-592 4-MeCONH-Ph 2,3-diMe-Ph 1-Nap
1-593 4-MeOCONH-Ph 2,3-diMe-Ph 1-Nap
1-594 4-MeSO₂NH-Ph 2,3-diMe-Ph 1-Nap
1-595 4-HCO-Ph 2,3-diMe-Ph 1-Nap
1-596 3-Ac-Ph 2,3-diMe-Ph 1-Nap
1-597 4-Ac-Ph 3-CF_Three-Ph 1-Nap
1-598 4-Ac-Ph 3-CF_Three-Ph 8-Qnl
1-599 4-Ac-Ph 2,3-diMe-Ph 1-Nap
1-600 4-Ac-Ph 2,3-diMe-Ph 8-Qnl
1-601 4-Ac-Ph 3-Pyr 1-Nap
1-602 4-Ac-Ph 3-Pyr 8-Qnl
1-603 4-Ac-Ph 2-MeO-3-Pyr 1-Nap
1-604 4-Ac-Ph 2-MeO-3-Pyr 8-Qnl
1-605 4-HOCO-Ph 2,3-diMe-Ph 1-Nap
1-606 4-MeOCO-Ph 2,3-diMe-Ph 1-Nap
1-607 2-EtOCO-Ph 2,3-diMe-Ph 1-Nap
1-608 3-EtOCO-Ph 2,3-diMe-Ph 1-Nap
1-609 4-EtOCO-Ph 2,3-diMe-Ph 1-Nap
1-610 4-tBuOCO-Ph 2,3-diMe-Ph 1-Nap
1-611 4-H₂NCO-Ph 2,3-diMe-Ph 1-Nap
1-612 4-MeNHCO-Ph 2,3-diMe-Ph 1-Nap
1-613 4-Me₂NCO-Ph 3-CF_Three-Ph 1-Nap
1-614 4-Me₂NCO-Ph 3-CF_Three-Ph 8-Qnl
1-615 4-Me₂NCO-Ph 2,3-diMe-Ph 1-Nap
1-616 4-Me₂NCO-Ph 2,3-diMe-Ph 8-Qnl
1-617 4-Me₂NCO-Ph 3-Pyr 1-Nap
1-618 4-Me₂NCO-Ph 3-Pyr 8-Qnl
1-619 4-Me₂NCO-Ph 2-MeO-3-Pyr 1-Nap
1-620 4-Me₂NCO-Ph 2-MeO-3-Pyr 8-Qnl
1-621 4-CN-Ph 2,3-diMe-Ph 1-Nap
1-622 4-CN-Ph 2,3-diMe-Ph 8-Qnl
1-623 4-CN-Ph 2-MeO-3-Pyr 1-Nap
1-624 4-CN-Ph 2-MeO-3-Pyr 8-Qnl
1-625 3-NO₂-Ph 2,3-diMe-Ph 1-Nap
1-626 4-NO₂-Ph 2,3-diMe-Ph 1-Nap
1-627 4-NO₂-Ph 2,3-diMe-Ph 8-Qnl
1-628 4-NO₂-Ph 2-MeO-3-Pyr 1-Nap
1-629 4-NO₂-Ph 2-MeO-3-Pyr 8-Qnl
1-630 2-F-Ph 2,3-diMe-Ph 1-Nap
1-631 3-F-Ph 2,3-diMe-Ph 1-Nap
1-632 4-F-Ph 2,3-diMe-Ph 1-Nap
1-633 2-Cl-Ph 2,3-diMe-Ph 1-Nap
1-634 3-Cl-Ph 2,3-diMe-Ph 1-Nap
1-635 4-Cl-Ph 2,3-diMe-Ph 1-Nap
1-636 4- (HOCOCH₂O) -Ph 2,3-diMe-Ph 1-Nap
1-637 4- (MeOCOCH₂O) -Ph 2,3-diMe-Ph 1-Nap
1-638 4- (tBuOCOCH₂O) -Ph 2,3-diMe-Ph 1-Nap
1-639 4- (tBuOCOCH₂O) -Ph 2-MeO-3-Pyr 8-Qnl
1-640 4- (H₂NCOCH₂O) -Ph 3-CF_Three-Ph 1-Nap
1-641 4- (H₂NCOCH₂O) -Ph 3-CF_Three-Ph 8-Qnl
1-642 4- (H₂NCOCH₂O) -Ph 2,3-diMe-Ph 1-Nap
1-643 4- (H₂NCOCH₂O) -Ph 2,3-diMe-Ph 8-Qnl
1-644 4- (H₂NCOCH₂O) -Ph 3-Pyr 1-Nap
1-645 4- (H₂NCOCH₂O) -Ph 3-Pyr 8-Qnl
1-646 4- (H₂NCOCH₂O) -Ph 2-MeO-3-Pyr 1-Nap
1-647 4- (H₂NCOCH₂O) -Ph 2-MeO-3-Pyr 8-Qnl
1-648 4- (H₂NCOCH₂O) -Ph 3-Odp 8-Qnl
1-649 4- (H₂NCOCH₂O) -Ph 4-Odp 8-Qnl
1-650 4- (MeNHCOCH₂O) -Ph 3-CF_Three-Ph 1-Nap
1-651 4- (MeNHCOCH₂O) -Ph 3-CF_Three-Ph 8-Qnl
1-652 4- (MeNHCOCH₂O) -Ph 2,3-diMe-Ph 1-Nap
1-653 4- (MeNHCOCH₂O) -Ph 2,3-diMe-Ph 8-Qnl
1-654 4- (MeNHCOCH₂O) -Ph 3-Pyr 1-Nap
1-655 4- (MeNHCOCH₂O) -Ph 3-Pyr 8-Qnl
1-656 4- (MeNHCOCH₂O) -Ph 2-MeO-3-Pyr 1-Nap
1-657 4- (MeNHCOCH₂O) -Ph 2-MeO-3-Pyr 8-Qnl
1-658 4- (Me₂NCOCH₂O) -Ph 3-CF_Three-Ph 1-Nap
1-659 4- (Me₂NCOCH₂O) -Ph 3-CF_Three-Ph 8-Qnl
1-660 4- (Me₂NCOCH₂O) -Ph 2,3-diMe-Ph 1-Nap
1-661 4- (Me₂NCOCH₂O) -Ph 2,3-diMe-Ph 8-Qnl
1-662 4- (Me₂NCOCH₂O) -Ph 3-Pyr 1-Nap
1-663 4- (Me₂NCOCH₂O) -Ph 3-Pyr 8-Qnl
1-664 4- (Me₂NCOCH₂O) -Ph 2-MeO-3-Pyr 1-Nap
1-665 4- (Me₂NCOCH₂O) -Ph 2-MeO-3-Pyr 8-Qnl
1-666 4- (HOCOCH₂) -Ph 2,3-diMe-Ph 1-Nap
1-667 4- (MeOCOCH₂) -Ph 2,3-diMe-Ph 1-Nap
1-668 3,4-Mtdo-Ph 2,3-diMe-Ph 1-Nap
1-669 3,4-Tmdo-Ph 2,3-diMe-Ph 1-Nap
1-670 3,4-Tmdo-Ph 2,3-diMe-Ph 8-Qnl
1-671 3,4-Tmdo-Ph 2-MeO-3-Pyr 1-Nap
1-672 3,4-Tmdo-Ph 2-MeO-3-Pyr 8-Qnl
1-673 2,3-diMe-Ph 2,3-diMe-Ph 1-Nap
1-674 2,4-diMe-Ph 2,3-diMe-Ph 1-Nap
1-675 2,5-diMe-Ph 2,3-diMe-Ph 1-Nap
1-676 2,6-diMe-Ph 2,3-diMe-Ph 1-Nap
1-677 3,4-diMe-Ph 2,3-diMe-Ph 1-Nap
1-678 3,5-diMe-Ph 2,3-diMe-Ph 1-Nap
1-679 2-Me-4-MeO-Ph 2,3-diMe-Ph 1-Nap
1-680 5-Me-2-MeO-Ph 2,3-diMe-Ph 1-Nap
1-681 6-Me-2-MeO-Ph 2,3-diMe-Ph 1-Nap
1-682 3-CF_Three-4-MeO-Ph 2,3-diMe-Ph 1-Nap
1-683 4- [HON = C (Me)]-3-OH-Ph 2,3-diMe-Ph 1-Nap
1-684 4- [HON = C (Me)]-3-OH-Ph 2,3-diMe-Ph 8-Qnl
1-685 4- [HON = C (Me)]-3-OH-Ph 2-MeO-3-Pyr 1-Nap
1-686 4- [HON = C (Me)]-3-OH-Ph 2-MeO-3-Pyr 8-Qnl
1-687 4- [MeON = C (Me)]-3-OH-Ph 2,3-diMe-Ph 1-Nap
1-688 3-HO-4-Ac-Ph 2,3-diMe-Ph 1-Nap
1-689 3-HO-4-Ac-Ph 2,3-diMe-Ph 8-Qnl
1-690 3-HO-4-Ac-Ph 2-MeO-3-Pyr 1-Nap
1-691 3-HO-4-Ac-Ph 2-MeO-3-Pyr 8-Qnl
1-692 2,3-diMeO-Ph 2,3-diMe-Ph 1-Nap
1-693 2,4-diMeO-Ph 2,3-diMe-Ph 1-Nap
1-694 2,5-diMeO-Ph 2,3-diMe-Ph 1-Nap
1-695 2,6-diMeO-Ph 2,3-diMe-Ph 1-Nap
1-696 3,4-diMeO-Ph 2,3-diMe-Ph 1-Nap
1-697 3,5-diMeO-Ph 2,3-diMe-Ph 1-Nap
1-698 2-MeO-5-MeOCO-Ph 2,3-diMe-Ph 1-Nap
1-699 3-MeO-4-MeOCO-Ph 2,3-diMe-Ph 1-Nap
1-700 4-MeO-3-F-Ph 2,3-diMe-Ph 1-Nap
1-701 2,3-diF-Ph 2,3-diMe-Ph 1-Nap
1-702 2,4-diF-Ph 2,3-diMe-Ph 1-Nap
1-703 2,5-diF-Ph 2,3-diMe-Ph 1-Nap
1-704 2,6-diF-Ph 2,3-diMe-Ph 1-Nap
1-705 3,4-diF-Ph 2,3-diMe-Ph 1-Nap
1-706 3,5-diF-Ph 2,3-diMe-Ph 1-Nap
1-707 2,3-diCl-Ph 2,3-diMe-Ph 1-Nap
1-708 2,4-diCl-Ph 2,3-diMe-Ph 1-Nap
1-709 2,5-diCl-Ph 2,3-diMe-Ph 1-Nap
1-710 2,6-diCl-Ph 2,3-diMe-Ph 1-Nap
1-711 3,4-diCl-Ph 2,3-diMe-Ph 1-Nap
1-712 3,5-diCl-Ph 2,3-diMe-Ph 1-Nap
1-713 3,4,5-triMeO-Ph 2,3-diMe-Ph 1-Nap
1-714 2-Ph-Ph 2,3-diMe-Ph 1-Nap
1-715 3-Ph-Ph 2,3-diMe-Ph 1-Nap
1-716 4-Ph-Ph 2,3-diMe-Ph 1-Nap
1-717 4- (1-Pyl) -Ph 3-CF_Three-Ph 1-Nap
1-718 4- (1-Pyl) -Ph 3-CF_Three-Ph 8-Qnl
1-719 4- (1-Pyl) -Ph 2,3-diMe-Ph 1-Nap
1-720 4- (1-Pyl) -Ph 2,3-diMe-Ph 4-Qnl
1-721 4- (1-Pyl) -Ph 2,3-diMe-Ph 5-Qnl
1-722 4- (1-Pyl) -Ph 2,3-diMe-Ph 8-Qnl
1-723 4- (1-Pyl) -Ph 2,3-diMe-Ph 1-Iql
1-724 4- (1-Pyl) -Ph 2,3-diMe-Ph 4-Iql
1-725 4- (1-Pyl) -Ph 2,3-diMe-Ph 5-Iql
1-726 4- (1-Pyl) -Ph 2,3-diMe-Ph 8-Iql
1-727 4- (1-Pyl) -Ph 2-MeO-3-Pyr 1-Nap
1-728 4- (1-Pyl) -Ph 2-MeO-3-Pyr 4-Qnl
1-729 4- (1-Pyl) -Ph 2-MeO-3-Pyr 5-Qnl
1-730 4- (1-Pyl) -Ph 2-MeO-3-Pyr 8-Qnl
1-731 4- (1-Pyl) -Ph 2-MeO-3-Pyr 1-Iql
1-732 4- (1-Pyl) -Ph 2-MeO-3-Pyr 4-Iql
1-733 4- (1-Pyl) -Ph 2-MeO-3-Pyr 5-Iql
1-734 4- (1-Pyl) -Ph 2-MeO-3-Pyr 8-Iql
1-735 4- (3-Pyl) -Ph 2,3-diMe-Ph 1-Nap
1-736 4- (3-Pyl) -Ph 2,3-diMe-Ph 8-Qnl
1-737 4- (3-Pyl) -Ph 2-MeO-3-Pyr 1-Nap
1-738 4- (3-Pyl) -Ph 2-MeO-3-Pyr 8-Qnl
1-739 4- (2-Fur) -Ph 2,3-diMe-Ph 1-Nap
1-740 4- (5-Me-4-EtOCO-2-Fur) -Ph 2,3-diMe-Ph 1-Nap
1-741 4- (2-Thi) -Ph 2,3-diMe-Ph 1-Nap
1-742 4- (2-Thi) -Ph 2,3-diMe-Ph 8-Qnl
1-743 4- (2-Thi) -Ph 2-MeO-3-Pyr 1-Nap
1-744 4- (2-Thi) -Ph 2-MeO-3-Pyr 8-Qnl
1-745 4- (2-Pyr) -Ph 2,3-diMe-Ph 1-Nap
1-746 4- (3-Pyr) -Ph 2,3-diMe-Ph 1-Nap
1-747 4- (4-Pyr) -Ph 2,3-diMe-Ph 1-Nap
1-748 4- (1-Prl) -Ph 3-CF_Three-Ph 1-Nap
1-749 4- (1-Prl) -Ph 3-CF_Three-Ph 8-Qnl
1-750 4- (1-Prl) -Ph 2,3-diMe-Ph 1-Nap
1-751 4- (1-Prl) -Ph 2,3-diMe-Ph 4-Qnl
1-752 4- (1-Prl) -Ph 2,3-diMe-Ph 5-Qnl
1-753 4- (1-Prl) -Ph 2,3-diMe-Ph 8-Qnl
1-754 4- (1-Prl) -Ph 2,3-diMe-Ph 1-Iql
1-755 4- (1-Prl) -Ph 2,3-diMe-Ph 4-Iql
1-756 4- (1-Prl) -Ph 2,3-diMe-Ph 5-Iql
1-757 4- (1-Prl) -Ph 2,3-diMe-Ph 8-Iql
1-758 4- (1-Prl) -Ph 2-MeO-3-Pyr 1-Nap
1-759 4- (1-Prl) -Ph 2-MeO-3-Pyr 4-Qnl
1-760 4- (1-Prl) -Ph 2-MeO-3-Pyr 5-Qnl
1-761 4- (1-Prl) -Ph 2-MeO-3-Pyr 8-Qnl
1-762 4- (1-Prl) -Ph 2-MeO-3-Pyr 1-Iql
1-763 4- (1-Prl) -Ph 2-MeO-3-Pyr 4-Iql
1-764 4- (1-Prl) -Ph 2-MeO-3-Pyr 5-Iql
1-765 4- (1-Prl) -Ph 2-MeO-3-Pyr 8-Iql
1-766 4- (3-Prl) -Ph 2,3-diMe-Ph 1-Nap
1-767 4- (3-Prl) -Ph 2,3-diMe-Ph 8-Qnl
1-768 4- (3-Prl) -Ph 2-MeO-3-Pyr 1-Nap
1-769 4- (3-Prl) -Ph 2-MeO-3-Pyr 8-Qnl
1-770 4- (3-Me-1-Prl) -Ph 2,3-diMe-Ph 1-Nap
1-771 4- (5-Me-1-Prl) -Ph 2,3-diMe-Ph 1-Nap
1-772 4- (1-Me-3-Prl) -Ph 2,3-diMe-Ph 1-Nap
1-773 4- (4-Me-3-Prl) -Ph 2,3-diMe-Ph 1-Nap
1-774 4- (3,5-diMe-1-Prl) -Ph 2,3-diMe-Ph 1-Nap
1-775 4- (1,4-diMe-3-Prl) -Ph 2,3-diMe-Ph 1-Nap
1-776 4- (5-Me-4-EtOCO-1-Prl) -Ph 2,3-diMe-Ph 1-Nap
1-777 4- (5-Me-4-EtOCO-1-Prl) -Ph 2,3-diMe-Ph 8-Qnl
1-778 4- (3-Me-5-Br-1-Prl) -Ph 2,3-diMe-Ph 1-Nap
1-779 4- (1-Me-4-Br-3-Prl) -Ph 2,3-diMe-Ph 1-Nap
1-780 4- (3,5-diMe-4-EtOCO-1-Prl) -Ph 2,3-diMe-Ph 1-Nap
1-781 4- (1-Imd) -Ph 3-CF_Three-Ph 1-Nap
1-782 4- (1-Imd) -Ph 3-CF_Three-Ph 4-Qnl
1-783 4- (1-Imd) -Ph 3-CF_Three-Ph 5-Qnl
1-784 4- (1-Imd) -Ph 3-CF_Three-Ph 8-Qnl
1-785 4- (1-Imd) -Ph 3-CF_Three-Ph 1-Iql
1-786 4- (1-Imd) -Ph 3-CF_Three-Ph 4-Iql
1-787 4- (1-Imd) -Ph 3-CF_Three-Ph 5-Iql
1-788 4- (1-Imd) -Ph 3-CF_Three-Ph 8-Iql
1-789 4- (1-Imd) -Ph 3-CF_Three-Ph 5-Qnz
1-790 4- (1-Imd) -Ph 3-CF_Three-Ph 8-Qnz
1-791 4- (1-Imd) -Ph 3-CF_Three-Ph 5-Qnx
1-792 4- (1-Imd) -Ph 3-CF_Three-Ph 8-Qnx
1-793 4- (1-Imd) -Ph 2,3-diMe-Ph 1-Nap
1-794 4- (1-Imd) -Ph 2,3-diMe-Ph 4-Me-1-Nap
1-795 4- (1-Imd) -Ph 2,3-diMe-Ph 5-Me-1-Nap
1-796 4- (1-Imd) -Ph 2,3-diMe-Ph 4-MeO-1-Nap
1-797 4- (1-Imd) -Ph 2,3-diMe-Ph 5-MeO-1-Nap
1-798 4- (1-Imd) -Ph 2,3-diMe-Ph 4-MeNH-1-Nap
1-799 4- (1-Imd) -Ph 2,3-diMe-Ph 5-MeNH-1-Nap
1-800 4- (1-Imd) -Ph 2,3-diMe-Ph 4-Me₂N-1-Nap
1-801 4- (1-Imd) -Ph 2,3-diMe-Ph 5-Me₂N-1-Nap
1-802 4- (1-Imd) -Ph 2,3-diMe-Ph 4-F-1-Nap
1-803 4- (1-Imd) -Ph 2,3-diMe-Ph 5-F-1-Nap
1-804 4- (1-Imd) -Ph 2,3-diMe-Ph 4-Cl-1-Nap
1-805 4- (1-Imd) -Ph 2,3-diMe-Ph 5-Cl-1-Nap
1-806 4- (1-Imd) -Ph 2,3-diMe-Ph 4-Qnl
1-807 4- (1-Imd) -Ph 2,3-diMe-Ph 5-Qnl
1-808 4- (1-Imd) -Ph 2,3-diMe-Ph 8-Qnl
1-809 4- (1-Imd) -Ph 2,3-diMe-Ph 4-Me-8-Qnl
1-810 4- (1-Imd) -Ph 2,3-diMe-Ph 5-Me-8-Qnl
1-811 4- (1-Imd) -Ph 2,3-diMe-Ph 4-MeO-8-Qnl
1-812 4- (1-Imd) -Ph 2,3-diMe-Ph 5-MeO-8-Qnl
1-813 4- (1-Imd) -Ph 2,3-diMe-Ph 4-MeNH-8-Qnl
1-814 4- (1-Imd) -Ph 2,3-diMe-Ph 5-MeNH-8-Qnl
1-815 4- (1-Imd) -Ph 2,3-diMe-Ph 4-Me₂N-8-Qnl
1-816 4- (1-Imd) -Ph 2,3-diMe-Ph 5-Me₂N-8-Qnl
1-817 4- (1-Imd) -Ph 2,3-diMe-Ph 4-F-8-Qnl
1-818 4- (1-Imd) -Ph 2,3-diMe-Ph 5-F-8-Qnl
1-819 4- (1-Imd) -Ph 2,3-diMe-Ph 4-Cl-8-Qnl
1-820 4- (1-Imd) -Ph 2,3-diMe-Ph 5-Cl-8-Qnl
1-821 4- (1-Imd) -Ph 2,3-diMe-Ph 1-Iql
1-822 4- (1-Imd) -Ph 2,3-diMe-Ph 4-Iql
1-823 4- (1-Imd) -Ph 2,3-diMe-Ph 5-Iql
1-824 4- (1-Imd) -Ph 2,3-diMe-Ph 8-Iql
1-825 4- (1-Imd) -Ph 2,3-diMe-Ph 5-Qnz
1-826 4- (1-Imd) -Ph 2,3-diMe-Ph 8-Qnz
1-827 4- (1-Imd) -Ph 2,3-diMe-Ph 5-Qnx
1-828 4- (1-Imd) -Ph 2,3-diMe-Ph 8-Qnx
1-829 4- (1-Imd) -Ph 2-Pyr 1-Nap
1-830 4- (1-Imd) -Ph 3-Pyr 1-Nap
1-831 4- (1-Imd) -Ph 4-Pyr 1-Nap
1-832 4- (1-Imd) -Ph 6-MeO-2-Pyr 1-Nap
1-833 4- (1-Imd) -Ph 2-MeO-3-Pyr 1-Nap
1-834 4- (1-Imd) -Ph 2-MeO-3-Pyr 4-Me-1-Nap
1-835 4- (1-Imd) -Ph 2-MeO-3-Pyr 5-Me-1-Nap
1-836 4- (1-Imd) -Ph 2-MeO-3-Pyr 4-MeO-1-Nap
1-837 4- (1-Imd) -Ph 2-MeO-3-Pyr 5-MeO-1-Nap
1-838 4- (1-Imd) -Ph 2-MeO-3-Pyr 4-MeNH-1-Nap
1-839 4- (1-Imd) -Ph 2-MeO-3-Pyr 5-MeNH-1-Nap
1-840 4- (1-Imd) -Ph 2-MeO-3-Pyr 4-Me₂N-1-Nap
1-841 4- (1-Imd) -Ph 2-MeO-3-Pyr 5-Me₂N-1-Nap
1-842 4- (1-Imd) -Ph 2-MeO-3-Pyr 4-F-1-Nap
1-843 4- (1-Imd) -Ph 2-MeO-3-Pyr 5-F-1-Nap
1-844 4- (1-Imd) -Ph 2-MeO-3-Pyr 4-Cl-1-Nap
1-845 4- (1-Imd) -Ph 2-MeO-3-Pyr 5-Cl-1-Nap
1-846 4- (1-Imd) -Ph 2-MeO-3-Pyr 4-Qnl
1-847 4- (1-Imd) -Ph 2-MeO-3-Pyr 5-Qnl
1-848 4- (1-Imd) -Ph 2-MeO-3-Pyr 8-Qnl
1-849 4- (1-Imd) -Ph 2-MeO-3-Pyr 4-Me-8-Qnl
1-850 4- (1-Imd) -Ph 2-MeO-3-Pyr 5-Me-8-Qnl
1-851 4- (1-Imd) -Ph 2-MeO-3-Pyr 4-MeO-8-Qnl
1-852 4- (1-Imd) -Ph 2-MeO-3-Pyr 5-MeO-8-Qnl
1-853 4- (1-Imd) -Ph 2-MeO-3-Pyr 4-MeNH-8-Qnl
1-854 4- (1-Imd) -Ph 2-MeO-3-Pyr 5-MeNH-8-Qnl
1-855 4- (1-Imd) -Ph 2-MeO-3-Pyr 4-Me₂N-8-Qnl
1-856 4- (1-Imd) -Ph 2-MeO-3-Pyr 5-Me₂N-8-Qnl
1-857 4- (1-Imd) -Ph 2-MeO-3-Pyr 4-F-8-Qnl
1-858 4- (1-Imd) -Ph 2-MeO-3-Pyr 5-F-8-Qnl
1-859 4- (1-Imd) -Ph 2-MeO-3-Pyr 4-Cl-8-Qnl
1-860 4- (1-Imd) -Ph 2-MeO-3-Pyr 5-Cl-8-Qnl
1-861 4- (1-Imd) -Ph 2-MeO-3-Pyr 1-Iql
1-862 4- (1-Imd) -Ph 2-MeO-3-Pyr 4-Iql
1-863 4- (1-Imd) -Ph 2-MeO-3-Pyr 5-Iql
1-864 4- (1-Imd) -Ph 2-MeO-3-Pyr 8-Iql
1-865 4- (1-Imd) -Ph 2-MeO-3-Pyr 5-Qnz
1-866 4- (1-Imd) -Ph 2-MeO-3-Pyr 8-Qnz
1-867 4- (1-Imd) -Ph 2-MeO-3-Pyr 5-Qnx
1-868 4- (1-Imd) -Ph 2-MeO-3-Pyr 8-Qnx
1-869 4- (1-Imd) -Ph 2-MeO-4-Pyr 1-Nap
1-870 4- (1-Imd) -Ph 2-MeO-4-Pyr 8-Qnl
1-871 4- (1-Imd) -Ph 3-Odp 1-Nap
1-872 4- (1-Imd) -Ph 3-Odp 8-Qnl
1-873 4- (1-Imd) -Ph 4-Odp 1-Nap
1-874 4- (1-Imd) -Ph 4-Odp 8-Qnl
1-875 4- (4-Me-1-Imd) -Ph 2,3-diMe-Ph 1-Nap
1-876 4- (4-Me-1-Imd) -Ph 2,3-diMe-Ph 8-Qnl
1-877 4- (4-Me-1-Imd) -Ph 2-MeO-3-Pyr 1-Nap
1-878 4- (4-Me-1-Imd) -Ph 2-MeO-3-Pyr 8-Qnl
1-879 4- (4-CF_Three-1-Imd) -Ph 2,3-diMe-Ph 1-Nap
1-880 4- (4-CF_Three-1-Imd) -Ph 2,3-diMe-Ph 8-Qnl
1-881 4- (4-CF_Three-1-Imd) -Ph 2-MeO-3-Pyr 1-Nap
1-882 4- (4-CF_Three-1-Imd) -Ph 2-MeO-3-Pyr 8-Qnl
1-883 4- (4-cPr-1-Imd) -Ph 2,3-diMe-Ph 1-Nap
1-884 4- (4-cPr-1-Imd) -Ph 2,3-diMe-Ph 8-Qnl
1-885 4- (4-cPr-1-Imd) -Ph 2-MeO-3-Pyr 1-Nap
1-886 4- (4-cPr-1-Imd) -Ph 2-MeO-3-Pyr 8-Qnl
1-887 4- [4- (C≡C) -1-Imd] -Ph 2,3-diMe-Ph 1-Nap
1-888 4- [4- (C≡C) -1-Imd] -Ph 2,3-diMe-Ph 8-Qnl
1-889 4- [4- (C≡C) -1-Imd] -Ph 2-MeO-3-Pyr 1-Nap
1-890 4- [4- (C≡C) -1-Imd] -Ph 2-MeO-3-Pyr 8-Qnl
1-891 4- (4-HO-1-Imd) -Ph 2,3-diMe-Ph 1-Nap
1-892 4- (4-HO-1-Imd) -Ph 2,3-diMe-Ph 8-Qnl
1-893 4- (4-HO-1-Imd) -Ph 2-MeO-3-Pyr 1-Nap
1-894 4- (4-HO-1-Imd) -Ph 2-MeO-3-Pyr 8-Qnl
1-895 4- (4-MeO-1-Imd) -Ph 2,3-diMe-Ph 1-Nap
1-896 4- (4-MeO-1-Imd) -Ph 2,3-diMe-Ph 8-Qnl
1-897 4- (4-MeO-1-Imd) -Ph 2-MeO-3-Pyr 1-Nap
1-898 4- (4-MeO-1-Imd) -Ph 2-MeO-3-Pyr 8-Qnl
1-899 4- (4-CF_ThreeO-1-Imd) -Ph 2,3-diMe-Ph 1-Nap
1-900 4- (4-CF_ThreeO-1-Imd) -Ph 2,3-diMe-Ph 8-Qnl
1-901 4- (4-CF_ThreeO-1-Imd) -Ph 2-MeO-3-Pyr 1-Nap
1-902 4- (4-CF_ThreeO-1-Imd) -Ph 2-MeO-3-Pyr 8-Qnl
1-903 4- (4-HCOO-1-Imd) -Ph 2,3-diMe-Ph 1-Nap
1-904 4- (4-HCOO-1-Imd) -Ph 2,3-diMe-Ph 8-Qnl
1-905 4- (4-HCOO-1-Imd) -Ph 2-MeO-3-Pyr 1-Nap
1-906 4- (4-HCOO-1-Imd) -Ph 2-MeO-3-Pyr 8-Qnl
1-907 4- (4-MeCOO-1-Imd) -Ph 2,3-diMe-Ph 1-Nap
1-908 4- (4-MeCOO-1-Imd) -Ph 2,3-diMe-Ph 8-Qnl
1-909 4- (4-MeCOO-1-Imd) -Ph 2-MeO-3-Pyr 1-Nap
1-910 4- (4-MeCOO-1-Imd) -Ph 2-MeO-3-Pyr 8-Qnl
1-911 4- (4-MeS-1-Imd) -Ph 2,3-diMe-Ph 1-Nap
1-912 4- (4-MeS-1-Imd) -Ph 2,3-diMe-Ph 8-Qnl
1-913 4- (4-MeS-1-Imd) -Ph 2-MeO-3-Pyr 1-Nap
1-914 4- (4-MeS-1-Imd) -Ph 2-MeO-3-Pyr 8-Qnl
1-915 4- (4-MeSO-1-Imd) -Ph 2,3-diMe-Ph 1-Nap
1-916 4- (4-MeSO-1-Imd) -Ph 2,3-diMe-Ph 8-Qnl
1-917 4- (4-MeOS-1-Imd) -Ph 2-MeO-3-Pyr 1-Nap
1-918 4- (4-MeSO-1-Imd) -Ph 2-MeO-3-Pyr 8-Qnl
1-919 4- (4-MeSO₂-1-Imd) -Ph 2,3-diMe-Ph 1-Nap
1-920 4- (4-MeSO₂-1-Imd) -Ph 2,3-diMe-Ph 8-Qnl
1-921 4- (4-MeOS₂-1-Imd) -Ph 2-MeO-3-Pyr 1-Nap
1-922 4- (4-MeSO₂-1-Imd) -Ph 2-MeO-3-Pyr 8-Qnl
1-923 4- (4-H₂N-1-Imd) -Ph 2,3-diMe-Ph 1-Nap
1-924 4- (4-H₂N-1-Imd) -Ph 2,3-diMe-Ph 8-Qnl
1-925 4- (4-H₂N-1-Imd) -Ph 2-MeO-3-Pyr 1-Nap
1-926 4- (4-H₂N-1-Imd) -Ph 2-MeO-3-Pyr 8-Qnl
1-927 4- (4-MeNH-1-Imd) -Ph 2,3-diMe-Ph 1-Nap
1-928 4- (4-MeNH-1-Imd) -Ph 2,3-diMe-Ph 8-Qnl
1-929 4- (4-MeNH-1-Imd) -Ph 2-MeO-3-Pyr 1-Nap
1-930 4- (4-MeNH-1-Imd) -Ph 2-MeO-3-Pyr 8-Qnl
1-931 4- (4-Me₂N-1-Imd) -Ph 2,3-diMe-Ph 1-Nap
1-932 4- (4-Me₂N-1-Imd) -Ph 2,3-diMe-Ph 8-Qnl
1-933 4- (4-Me₂N-1-Imd) -Ph 2-MeO-3-Pyr 1-Nap
1-934 4- (4-Me₂N-1-Imd) -Ph 2-MeO-3-Pyr 8-Qnl
1-935 4- (4-HCONH-1-Imd) -Ph 2,3-diMe-Ph 1-Nap
1-936 4- (4-HCONH-1-Imd) -Ph 2,3-diMe-Ph 8-Qnl
1-937 4- (4-HCONH-1-Imd) -Ph 2-MeO-3-Pyr 1-Nap
1-938 4- (4-HCONH-1-Imd) -Ph 2-MeO-3-Pyr 8-Qnl
1-939 4- (4-MeCONH-1-Imd) -Ph 2,3-diMe-Ph 1-Nap
1-940 4- (4-MeCONH-1-Imd) -Ph 2,3-diMe-Ph 8-Qnl
1-941 4- (4-MeCONH-1-Imd) -Ph 2-MeO-3-Pyr 1-Nap
1-942 4- (4-MeCONH-1-Imd) -Ph 2-MeO-3-Pyr 8-Qnl
1-943 4- (4-MeOCONH-1-Imd) -Ph 2,3-diMe-Ph 1-Nap
1-944 4- (4-MeOCONH-1-Imd) -Ph 2,3-diMe-Ph 8-Qnl
1-945 4- (4-MeOCONH-1-Imd) -Ph 2-MeO-3-Pyr 1-Nap
1-946 4- (4-MeOCONH-1-Imd) -Ph 2-MeO-3-Pyr 8-Qnl
1-947 4- (4-HOCO-1-Imd) -Ph 2,3-diMe-Ph 1-Nap
1-948 4- (4-HOCO-1-Imd) -Ph 2,3-diMe-Ph 8-Qnl
1-949 4- (4-HOCO-1-Imd) -Ph 2-MeO-3-Pyr 1-Nap
1-950 4- (4-HOCO-1-Imd) -Ph 2-MeO-3-Pyr 8-Qnl
1-951 4- (4-MeOCO-1-Imd) -Ph 2,3-diMe-Ph 1-Nap
1-952 4- (4-MeOCO-1-Imd) -Ph 2,3-diMe-Ph 8-Qnl
1-953 4- (4-MeOCO-1-Imd) -Ph 2-MeO-3-Pyr 1-Nap
1-954 4- (4-MeOCO-1-Imd) -Ph 2-MeO-3-Pyr 8-Qnl
1-955 4- (4-H₂NCO-1-Imd) -Ph 2,3-diMe-Ph 1-Nap
1-956 4- (4-H₂NCO-1-Imd) -Ph 2,3-diMe-Ph 8-Qnl
1-957 4- (4-H₂NCO-1-Imd) -Ph 2-MeO-3-Pyr 1-Nap
1-958 4- (4-H₂NCO-1-Imd) -Ph 2-MeO-3-Pyr 8-Qnl
1-959 4- (4-MeNHCO-1-Imd) -Ph 2,3-diMe-Ph 1-Nap
1-960 4- (4-MeNHCO-1-Imd) -Ph 2,3-diMe-Ph 8-Qnl
1-961 4- (4-MeNHCO-1-Imd) -Ph 2-MeO-3-Pyr 1-Nap
1-962 4- (4-MeNHCO-1-Imd) -Ph 2-MeO-3-Pyr 8-Qnl
1-963 4- (4-Me₂NCO-1-Imd) -Ph 2,3-diMe-Ph 1-Nap
1-964 4- (4-Me₂NCO-1-Imd) -Ph 2,3-diMe-Ph 8-Qnl
1-965 4- (4-Me₂NCO-1-Imd) -Ph 2-MeO-3-Pyr 1-Nap
1-966 4- (4-Me₂NCO-1-Imd) -Ph 2-MeO-3-Pyr 8-Qnl
1-967 4- (4-NC-1-Imd) -Ph 2,3-diMe-Ph 1-Nap
1-968 4- (4-NC-1-Imd) -Ph 2,3-diMe-Ph 8-Qnl
1-969 4- (4-NC-1-Imd) -Ph 2-MeO-3-Pyr 1-Nap
1-970 4- (4-NC-1-Imd) -Ph 2-MeO-3-Pyr 8-Qnl
1-971 4- (4-NO₂-1-Imd) -Ph 2,3-diMe-Ph 1-Nap
1-972 4- (4-NO₂-1-Imd) -Ph 2,3-diMe-Ph 8-Qnl
1-973 4- (4-NO₂-1-Imd) -Ph 2-MeO-3-Pyr 1-Nap
1-974 4- (4-NO₂-1-Imd) -Ph 2-MeO-3-Pyr 8-Qnl
1-975 4- (4-F-1-Imd) -Ph 2,3-diMe-Ph 1-Nap
1-976 4- (4-F-1-Imd) -Ph 2,3-diMe-Ph 8-Qnl
1-977 4- (4-F-1-Imd) -Ph 2-MeO-3-Pyr 1-Nap
1-978 4- (4-F-1-Imd) -Ph 2-MeO-3-Pyr 8-Qnl
1-979 4- (4-Cl-1-Imd) -Ph 2,3-diMe-Ph 1-Nap
1-980 4- (4-Cl-1-Imd) -Ph 2,3-diMe-Ph 8-Qnl
1-981 4- (4-Cl-1-Imd) -Ph 2-MeO-3-Pyr 1-Nap
1-982 4- (4-Cl-1-Imd) -Ph 2-MeO-3-Pyr 8-Qnl
1-983 4- (3,4-Mtdo-1-Imd) -Ph 2,3-diMe-Ph 1-Nap
1-984 4- (3,4-Mtdo-1-Imd) -Ph 2,3-diMe-Ph 8-Qnl
1-985 4- (3,4-Mtdo-1-Imd) -Ph 2-MeO-3-Pyr 1-Nap
1-986 4- (3,4-Mtdo-1-Imd) -Ph 2-MeO-3-Pyr 8-Qnl
1-987 4- (4,5-diMe-1-Imd) -Ph 2,3-diMe-Ph 1-Nap
1-988 4- (4,5-diMeO-1-Imd) -Ph 2,3-diMe-Ph 1-Nap
1-989 4- (4,5-diF-1-Imd) -Ph 2,3-diMe-Ph 1-Nap
1-990 4- (4,5-diF-1-Imd) -Ph 2,3-diMe-Ph 8-Qnl
1-991 4- (4,5-diCl-1-Imd) -Ph 2,3-diMe-Ph 1-Nap
1-992 4- (4,5-diCl-1-Imd) -Ph 2,3-diMe-Ph 8-Qnl
1-993 4- (5-Oxz) -Ph 2,3-diMe-Ph 1-Nap
1-994 4- (5-Oxz) -Ph 2,3-diMe-Ph 8-Qnl
1-995 4- (5-Oxz) -Ph 2-MeO-3-Pyr 1-Nap
1-996 4- (5-Oxz) -Ph 2-MeO-3-Pyr 8-Qnl
1-997 4- (4-Me-2-Oxz) -Ph 2,3-diMe-Ph 1-Nap
1-998 4- (4-EtOCO-2-Oxz) -Ph 2,3-diMe-Ph 1-Nap
1-999 4- (5-Thz) -Ph 2,3-diMe-Ph 1-Nap
1-1000 4- (5-Thz) -Ph 2,3-diMe-Ph 8-Qnl
1-1001 4- (5-Thz) -Ph 2-MeO-3-Pyr 1-Nap
1-1002 4- (5-Thz) -Ph 2-MeO-3-Pyr 8-Qnl
1-1003 4- (4-Me-2-Thz) -Ph 2,3-diMe-Ph 1-Nap
1-1004 4- [1- (1,2,4-Taz)]-Ph 2,3-diMe-Ph 1-Nap
1-1005 4- [1- (1,2,4-Taz)]-Ph 2,3-diMe-Ph 8-Qnl
1-1006 4- [1- (1,2,4-Taz)]-Ph 2-MeO-3-Pyr 1-Nap
1-1007 4- [1- (1,2,4-Taz)]-Ph 2-MeO-3-Pyr 8-Qnl
1-1008 4- [4- (1,2,3-Odz)]-Ph 2,3-diMe-Ph 1-Nap
1-1009 4- [1- (1,2,4-Odz)]-Ph 2,3-diMe-Ph 8-Qnl
1-1010 4- [1- (1,2,4-Odz)]-Ph 2-MeO-3-Pyr 1-Nap
1-1011 4- [1- (1,2,4-Odz)]-Ph 2-MeO-3-Pyr 8-Qnl
1-1012 4- [4- (1,2,3-Tdz)]-Ph 2,3-diMe-Ph 1-Nap
1-1013 4- [1- (1,2,4-Tdz)]-Ph 2,3-diMe-Ph 8-Qnl
1-1014 4- [1- (1,2,4-Tdz)]-Ph 2-MeO-3-Pyr 1-Nap
1-1015 4- [1- (1,2,4-Tdz)]-Ph 2-MeO-3-Pyr 8-Qnl
1-1016 4- (5-Tet) -Ph 2,3-diMe-Ph 1-Nap
1-1017 4- (1-Pyrd) -Ph 2,3-diMe-Ph 1-Nap
1-1018 4- (1-Pyrd) -Ph 2-MeO-3-Pyr 1-Nap
1-1019 4- (1-Pip) -Ph 2,3-diMe-Ph 1-Nap
1-1020 4- (1-Pip) -Ph 2,3-diMe-Ph 8-Qnl
1-1021 4- (1-Pip) -Ph 2-MeO-3-Pyr 1-Nap
1-1022 4- (1-Pip) -Ph 2-MeO-3-Pyr 8-Qnl
1-1023 4- (1-Pipz) -Ph 2,3-diMe-Ph 1-Nap
1-1024 4- (1-Pipz) -Ph 2,3-diMe-Ph 8-Qnl
1-1025 4- (1-Pipz) -Ph 2-MeO-3-Pyr 1-Nap
1-1026 4- (1-Pipz) -Ph 2-MeO-3-Pyr 8-Qnl
1-1027 4- (4-Me-1-Pipz) -Ph 2,3-diMe-Ph 1-Nap
1-1028 4- (4-Me-1-Pipz) -Ph 2,3-diMe-Ph 8-Qnl
1-1029 4- (4-Me-1-Pipz) -Ph 2-MeO-3-Pyr 1-Nap
1-1030 4- (4-Me-1-Pipz) -Ph 2-MeO-3-Pyr 8-Qnl
1-1031 4- (4-Mor) -Ph 2,3-diMe-Ph 1-Nap
1-1032 4- (4-Mor) -Ph 2,3-diMe-Ph 8-Qnl
1-1033 4- (4-Mor) -Ph 2-MeO-3-Pyr 1-Nap
1-1034 4- (4-Mor) -Ph 2-MeO-3-Pyr 8-Qnl
1-1035 4- (4-Thm) -Ph 2,3-diMe-Ph 1-Nap
1-1036 4- (4-Thm) -Ph 2,3-diMe-Ph 8-Qnl
1-1037 4- (4-Thm) -Ph 2-MeO-3-Pyr 1-Nap
1-1038 4- (4-Thm) -Ph 2-MeO-3-Pyr 8-Qnl
1-1039 4- (3-Thdt) -Ph 2,3-diMe-Ph 1-Nap
1-1040 4- (3-Thdt) -Ph 2,3-diMe-Ph 4-F-1-Nap
1-1041 4- (3-Thdt) -Ph 2,3-diMe-Ph 8-Qnl
1-1042 4- (3-Thdt) -Ph 2,3-diMe-Ph 4-F-8-Qnl
1-1043 4- (4-Me-3-Thdt) -Ph 2,3-diMe-Ph 1-Nap
1-1044 4- (4-Me-3-Thdt) -Ph 2,3-diMe-Ph 4-F-1-Nap
1-1045 4- (4-Me-3-Thdt) -Ph 2,3-diMe-Ph 8-Qnl
1-1046 4- (4-Me-3-Thdt) -Ph 2,3-diMe-Ph 4-F-8-Qnl
1-1047 3-PhO-Ph 2,3-diMe-Ph 1-Nap
1-1048 4-PhO-Ph 2,3-diMe-Ph 1-Nap
1-1049 4-PhCO-Ph 2,3-diMe-Ph 1-Nap
1-1050 1-Nap 2,3-diMe-Ph 1-Nap
1-1051 2-Nap 2,3-diMe-Ph 1-Nap
1-1052 1-Idan 2,3-diMe-Ph 1-Nap
1-1053 2-Idan 2,3-diMe-Ph 1-Nap
1-1054 1-Iden 2,3-diMe-Ph 1-Nap
1-1055 2-Iden 2,3-diMe-Ph 1-Nap
1-1056 2-Fur 2,3-diMe-Ph 1-Nap
1-1057 5-MeOCO-2-Fur 2,3-diMe-Ph 1-Nap
1-1058 2-Thi 2,3-diMe-Ph 1-Nap
1-1059 5-Prl 2,3-diMe-Ph 1-Nap
1-1060 1-Me-5-Prl 2,3-diMe-Ph 1-Nap
1-1061 1,3-diMe-5-Prl 2,3-diMe-Ph 1-Nap
1-1062 1-Me-3-cPr-5-Prl 2,3-diMe-Ph 1-Nap
1-1063 2-Imd 2,3-diMe-Ph 1-Nap
1-1064 5-Imd 2,3-diMe-Ph 1-Nap
1-1065 2-Oxz 2,3-diMe-Ph 1-Nap
1-1066 3-Iox 2,3-diMe-Ph 1-Nap
1-1067 5-tBu-3-Iox 2,3-diMe-Ph 1-Nap
1-1068 2-Thz 2,3-diMe-Ph 1-Nap
1-1069 4-Me-2-Thz 2,3-diMe-Ph 1-Nap
1-1070 5-Me-2-Thz 2,3-diMe-Ph 1-Nap
1-1071 4-tBu-2-Thz 2,3-diMe-Ph 1-Nap
1-1072 5-Cl-2-Thz 2,3-diMe-Ph 1-Nap
1-1073 4- (EtOCOCH₂) -2-Thz 2,3-diMe-Ph 1-Nap
1-1074 4,5-diMe-2-Thz 2,3-diMe-Ph 1-Nap
1-1075 4-Me-5-Ac-2-Thz 2,3-diMe-Ph 1-Nap
1-1076 4-Me-5-Ac-2-Thz 2,3-diMe-Ph 8-Qnl
1-1077 4-Me-5-Ac-2-Thz 2-MeO-3-Pyr 1-Nap
1-1078 4-Me-5-Ac-2-Thz 2-MeO-3-Pyr 8-Qnl
1-1079 5-Ith 2,3-diMe-Ph 1-Nap
1-1080 3-Me-5-Ith 2,3-diMe-Ph 1-Nap
1-1081 3-Me-5-Ith 2,3-diMe-Ph 8-Qnl
1-1082 3-Me-5-Ith 2-MeO-3-Pyr 1-Nap
1-1083 3-Me-5-Ith 2-MeO-3-Pyr 8-Qnl
1-1084 3- (1,2,4-Taz) 2,3-diMe-Ph 1-Nap
1-1085 2- (1,3,4-Odz) 2,3-diMe-Ph 1-Nap
1-1086 2- (1,3,4-Tdz) 2,3-diMe-Ph 1-Nap
1-1087 5-tBu-2- (1,3,4-Tdz) 2,3-diMe-Ph 1-Nap
1-1088 5-cPr-2- (1,3,4-Tdz) 2,3-diMe-Ph 1-Nap
1-1089 2-Pyr 2,3-diMe-Ph 1-Nap
1-1090 3-Pyr 2,3-diMe-Ph 1-Nap
1-1091 4-Pyr 2,3-diMe-Ph 1-Nap
1-1092 5-Me-2-Pyr 2,3-diMe-Ph 1-Nap
1-1093 6-Me-3-Pyr 2,3-diMe-Ph 1-Nap
1-1094 6-Me-3-Pyr 2,3-diMe-Ph 8-Qnl
1-1095 6-Me-3-Pyr 2-MeO-3-Pyr 1-Nap
1-1096 6-Me-3-Pyr 2-MeO-3-Pyr 8-Qnl
1-1097 6-MeO-3-Pyr 2,3-diMe-Ph 1-Nap
1-1098 6-MeO-3-Pyr 2,3-diMe-Ph 8-Qnl
1-1099 6-MeO-3-Pyr 2-MeO-3-Pyr 1-Nap
1-1100 6-MeO-3-Pyr 2-MeO-3-Pyr 8-Qnl
1-1101 6-Cl-3-Pyr 2,3-diMe-Ph 1-Nap
1-1102 6-Cl-3-Pyr 2,3-diMe-Ph 8-Qnl
1-1103 6-Cl-3-Pyr 2-MeO-3-Pyr 1-Nap
1-1104 6-Cl-3-Pyr 2-MeO-3-Pyr 8-Qnl
1-1105 4-Pip 2,3-diMe-Ph 1-Nap
1-1106 1-EtOCO-4-Pip 2,3-diMe-Ph 1-Nap
1-1107 3-Ph-5-Prl 2,3-diMe-Ph 1-Nap
1-1108 1-Me-3-Ph-5-Prl 2,3-diMe-Ph 1-Nap
1-1109 3-Ph-5-Imd 2,3-diMe-Ph 1-Nap
1-1110 4-Ph-2-Imd 2,3-diMe-Ph 1-Nap
1-1111 4-Ph-2-Oxz 2,3-diMe-Ph 1-Nap
1-1112 4-Ph-2-Thz 2,3-diMe-Ph 1-Nap
1-1113 5-Me-4- (4-Cl-Ph) -2-Thz 2,3-diMe-Ph 1-Nap
1-1114 3-Ph-5- (1,2,4-Odz) 2,3-diMe-Ph 1-Nap
1-1115 3-Ph-5- (1,2,4-Tdz) 2,3-diMe-Ph 1-Nap
1-1116 5-Ph-3- (1,2,4-Taz) 2,3-diMe-Ph 1-Nap
1-1117 4-Ph-2-Pyr 2,3-diMe-Ph 1-Nap
1-1118 5-Ph-3-Pyr 2,3-diMe-Ph 1-Nap
1-1119 2-Ph-4-Pyr 2,3-diMe-Ph 1-Nap
1-1120 3- (1-Pyl) -5-Prl 2,3-diMe-Ph 1-Nap
1-1121 3- (2-Thi) -5 Prl 2,3-diMe-Ph 1-Nap
1-1122 1-Me-3- (2-Thi) -5-Prl 2,3-diMe-Ph 1-Nap
1-1123 3- (1-Prl) -5-Prl 2,3-diMe-Ph 1-Nap
1-1124 3- (1-Imd) -5-Prl 2,3-diMe-Ph 1-Nap
1-1125 3- (1-Imd) -5-Prl 2,3-diMe-Ph 8-Qnl
1-1126 3- (1-Imd) -5-Prl 2-MeO-3-Pyr 1-Nap
1-1127 3- (1-Imd) -5-Prl 2-MeO-3-Pyr 8-Qnl
1-1128 3- (2-Oxz) -5-Prl 2,3-diMe-Ph 1-Nap
1-1129 3- (2-Thz) -5-Prl 2,3-diMe-Ph 1-Nap
1-1130 3- (3-Pyr) -5-Prl 2,3-diMe-Ph 1-Nap
1-1131 4- (1-Pyl) -2-Thi 2,3-diMe-Ph 1-Nap
1-1132 4- (2-Thi) -2-Thi 2,3-diMe-Ph 1-Nap
1-1133 4- (1-Prl) -2-Thi 2,3-diMe-Ph 1-Nap
1-1134 4- (1-Imd) -2-Thi 2,3-diMe-Ph 1-Nap
1-1135 4- (1-Imd) -2-Thi 2,3-diMe-Ph 8-Qnl
1-1136 4- (1-Imd) -2-Thi 2-MeO-3-Pyr 1-Nap
1-1137 4- (1-Imd) -2-Thi 2-MeO-3-Pyr 8-Qnl
1-1138 4- (2-Oxz) -2-Thi 2,3-diMe-Ph 1-Nap
1-1139 4- (2-Thz) -2-Thi 2,3-diMe-Ph 1-Nap
1-1140 4- (3-Pyr) -2-Thi 2,3-diMe-Ph 1-Nap
1-1141 4- (1-Pyl) -2-Imd 2,3-diMe-Ph 1-Nap
1-1142 4- (2-Thi) -2-Imd 2,3-diMe-Ph 1-Nap
1-1143 4- (1-Prl) -2-Imd 2,3-diMe-Ph 1-Nap
1-1144 4- (1-Imd) -2-Imd 2,3-diMe-Ph 1-Nap
1-1145 4- (1-Imd) -2-Imd 2,3-diMe-Ph 8-Qnl
1-1146 4- (1-Imd) -2-Imd 2-MeO-3-Pyr 1-Nap
1-1147 4- (1-Imd) -2-Imd 2-MeO-3-Pyr 8-Qnl
1-1148 4- (2-Oxz) -2-Imd 2,3-diMe-Ph 1-Nap
1-1149 4- (2-Thz) -2-Imd 2,3-diMe-Ph 1-Nap
1-1150 4- (3-Pyr) -2-Imd 2,3-diMe-Ph 1-Nap
1-1151 4- (1-Pyl) -2-Thz 2,3-diMe-Ph 1-Nap
1-1152 4- (2-Thi) -2-Thz 2,3-diMe-Ph 1-Nap
1-1153 4- (5-Me-2-Thi) -2-Thz 2,3-diMe-Ph 1-Nap
1-1154 4- (1-Prl) -2-Thz 2,3-diMe-Ph 1-Nap
1-1155 4- (1-Imd) -2-Thz 2,3-diMe-Ph 1-Nap
1-1156 4- (1-Imd) -2-Thz 2,3-diMe-Ph 8-Qnl
1-1157 4- (1-Imd) -2-Thz 2-MeO-3-Pyr 1-Nap
1-1158 4- (1-Imd) -2-Thz 2-MeO-3-Pyr 8-Qnl
1-1159 4- (2-Oxz) -2-Thz 2,3-diMe-Ph 1-Nap
1-1160 4- (2-Thz) -2-Thz 2,3-diMe-Ph 1-Nap
1-1161 4- (3-Pyr) -2-Thz 2,3-diMe-Ph 1-Nap
1-1162 4- (1-Pyl) -2-Pyr 2,3-diMe-Ph 1-Nap
1-1163 4- (2-Thi) -2-Pyr 2,3-diMe-Ph 1-Nap
1-1164 4- (1-Prl) -2-Pyr 2,3-diMe-Ph 1-Nap
1-1165 4- (1-Imd) -2-Pyr 2,3-diMe-Ph 1-Nap
1-1166 4- (1-Imd) -2-Pyr 2,3-diMe-Ph 8-Qnl
1-1167 4- (1-Imd) -2-Pyr 2-MeO-3-Pyr 1-Nap
1-1168 4- (1-Imd) -2-Pyr 2-MeO-3-Pyr 8-Qnl
1-1169 4- (2-Oxz) -2-Pyr 2,3-diMe-Ph 1-Nap
1-1170 4- (2-Thz) -2-Pyr 2,3-diMe-Ph 1-Nap
1-1171 4- (3-Pyr) -2-Pyr 2,3-diMe-Ph 1-Nap
1-1172 4- (1-Pyl) -3-Pyr 2,3-diMe-Ph 1-Nap
1-1173 4- (2-Thi) -3-Pyr 2,3-diMe-Ph 1-Nap
1-1174 4- (1-Prl) -3-Pyr 2,3-diMe-Ph 1-Nap
1-1175 4- (1-Imd) -3-Pyr 2,3-diMe-Ph 1-Nap
1-1176 4- (1-Imd) -3-Pyr 2,3-diMe-Ph 8-Qnl
1-1177 4- (1-Imd) -3-Pyr 2-MeO-3-Pyr 1-Nap
1-1178 4- (1-Imd) -3-Pyr 2-MeO-3-Pyr 8-Qnl
1-1179 4- (2-Oxz) -3-Pyr 2,3-diMe-Ph 1-Nap
1-1180 4- (2-Thz) -3-Pyr 2,3-diMe-Ph 1-Nap
1-1181 4- (3-Pyr) -3-Pyr 2,3-diMe-Ph 1-Nap
1-1182 6- (4-Mor) -3-Pyr 2,3-diMe-Ph 1-Nap
1-1183 6- (4-Mor) -3-Pyr 2,3-diMe-Ph 8-Qnl
1-1184 6- (4-Mor) -3-Pyr 2-MeO-3-Pyr 1-Nap
1-1185 6- (4-Mor) -3-Pyr 2-MeO-3-Pyr 8-Qnl
1-1186 3- (1-Pyl) -4-Pyr 2,3-diMe-Ph 1-Nap
1-1187 3- (2-Thi) -4-Pyr 2,3-diMe-Ph 1-Nap
1-1188 3- (1-Prl) -4-Pyr 2,3-diMe-Ph 1-Nap
1-1189 3- (1-Imd) -4-Pyr 2,3-diMe-Ph 1-Nap
1-1190 3- (1-Imd) -4-Pyr 2,3-diMe-Ph 8-Qnl
1-1191 3- (1-Imd) -4-Pyr 2-MeO-3-Pyr 1-Nap
1-1192 3- (1-Imd) -4-Pyr 2-MeO-3-Pyr 8-Qnl
1-1193 3- (2-Oxz) -4-Pyr 2,3-diMe-Ph 1-Nap
1-1194 3- (2-Thz) -4-Pyr 2,3-diMe-Ph 1-Nap
1-1195 3- (3-Pyr) -4-Pyr 2,3-diMe-Ph 1-Nap
1-1196 4-Qnl 2,3-diMe-Ph 1-Nap
1-1197 5-Qnl 2,3-diMe-Ph 1-Nap
1-1198 6-Qnl 2,3-diMe-Ph 1-Nap
1-1199 8-Qnl 2,3-diMe-Ph 1-Nap
1-1200 5-Qnz 2,3-diMe-Ph 1-Nap
1-1201 5-Qnx 2,3-diMe-Ph 1-Nap
￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣

(Table 2)

￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣
Illustrative compound number A ¹ A ² A ³ R ¹ R ²
￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣
2-1 4-Ph 2,3-diMe-Ph 1-Nap CO H
2-2 4-Me-Ph 2,3-diMe-Ph 1-Nap CO H
2-3 4-MeO-Ph 3-CF ₃ -Ph 1-Nap CO H
2-4 4-MeO-Ph 3-CF ₃ -Ph 1-Nap NHCO Me
2-5 4-MeO-Ph 3-CF ₃ -Ph 1-Nap NMeCO H
2-6 2-MeO-Ph 2,3-diMe-Ph 1-Nap CO H
2-7 3-MeO-Ph 2,3-diMe-Ph 1-Nap CO H
2-8 4-MeO-Ph 2,3-diMe-Ph 1-Nap CO H
2-9 4-MeO-Ph 2,3-diMe-Ph 1-Nap NHCO Me
2-10 4-MeO-Ph 2,3-diMe-Ph 1-Nap NMeCO H
2-11 4-MeO-Ph 2,3-diMe-Ph 8-Qnl CO H
2-12 4-MeO-Ph 2,3-diMe-Ph 8-Qnl NHCO Me
2-13 4-MeO-Ph 2,3-diMe-Ph 8-Qnl NMeCO H
2-14 4-MeO-Ph 2-MeO-3-Pyr 1-Nap CO H
2-15 4-MeO-Ph 2-MeO-3-Pyr 1-Nap NHCO Me
2-16 4-MeO-Ph 2-MeO-3-Pyr 1-Nap NMeCO H
2-17 4-MeO-Ph 2-MeO-3-Pyr 8-Qnl CO H
2-18 4-MeO-Ph 2-MeO-3-Pyr 8-Qnl NHCO Me
2-19 4-MeO-Ph 2-MeO-3-Pyr 8-Qnl NMeCO H
2-20 4-EtO-Ph 3-CF ₃ -Ph 1-Nap CO H
2-21 4-EtO-Ph 3-CF ₃ -Ph 1-Nap NHCO Me
2-22 4-EtO-Ph 3-CF ₃ -Ph 1-Nap NMeCO H
2-23 4-EtO-Ph 2,3-diMe-Ph 1-Nap CO H
2-24 4-EtO-Ph 2,3-diMe-Ph 1-Nap CO Me
2-25 4-EtO-Ph 2,3-diMe-Ph 1-Nap NHCO Me
2-26 4-EtO-Ph 2,3-diMe-Ph 1-Nap NHCO Et
2-27 4-EtO-Ph 2,3-diMe-Ph 1-Nap NMeCO H
2-28 4-EtO-Ph 2,3-diMe-Ph 1-Nap NMeCO Me
2-29 4-EtO-Ph 2,3-diMe-Ph 8-Qnl CO H
2-30 4-EtO-Ph 2,3-diMe-Ph 8-Qnl CO Me
2-31 4-EtO-Ph 2,3-diMe-Ph 8-Qnl NHCO Me
2-32 4-EtO-Ph 2,3-diMe-Ph 8-Qnl NHCO Et
2-33 4-EtO-Ph 2,3-diMe-Ph 8-Qnl NMeCO H
2-34 4-EtO-Ph 2,3-diMe-Ph 8-Qnl NMeCO Me
2-35 4-EtO-Ph 2-MeO-3-Pyr 1-Nap CO H
2-36 4-EtO-Ph 2-MeO-3-Pyr 1-Nap CO Me
2-37 4-EtO-Ph 2-MeO-3-Pyr 1-Nap NHCO Me
2-38 4-EtO-Ph 2-MeO-3-Pyr 1-Nap NHCO Et
2-39 4-EtO-Ph 2-MeO-3-Pyr 1-Nap NMeCO H
2-40 4-EtO-Ph 2-MeO-3-Pyr 1-Nap NMeCO Me
2-41 4-EtO-Ph 2-MeO-3-Pyr 8-Qnl CO H
2-42 4-EtO-Ph 2-MeO-3-Pyr 8-Qnl CO Me
2-43 4-EtO-Ph 2-MeO-3-Pyr 8-Qnl NHCO Me
2-44 4-EtO-Ph 2-MeO-3-Pyr 8-Qnl NHCO Et
2-45 4-EtO-Ph 2-MeO-3-Pyr 8-Qnl NMeCO H
2-46 4-EtO-Ph 2-MeO-3-Pyr 8-Qnl NMeCO Me
2-47 4-nPrO-Ph 3-CF ₃ -Ph 1-Nap CO H
2-48 4-nPrO-Ph 3-CF ₃ -Ph 1-Nap NHCO Me
2-49 4-nPrO-Ph 3-CF ₃ -Ph 1-Nap NMeCO H
2-50 2-nPrO-Ph 2,3-diMe-Ph 1-Nap CO H
2-51 3-nPrO-Ph 2,3-diMe-Ph 1-Nap CO H
2-52 4-nPrO-Ph 2,3-diMe-Ph 1-Nap CO H
2-53 4-nPrO-Ph 2,3-diMe-Ph 1-Nap NHCO Me
2-54 4-nPrO-Ph 2,3-diMe-Ph 1-Nap NMeCO H
2-55 4-nPrO-Ph 2,3-diMe-Ph 8-Qnl CO H
2-56 4-nPrO-Ph 2,3-diMe-Ph 8-Qnl NHCO Me
2-57 4-nPrO-Ph 2,3-diMe-Ph 8-Qnl NMeCO H
2-58 4-nPrO-Ph 2-MeO-3-Pyr 1-Nap CO H
2-59 4-nPrO-Ph 2-MeO-3-Pyr 1-Nap NHCO Me
2-60 4-nPrO-Ph 2-MeO-3-Pyr 1-Nap NMeCO H
2-61 4-nPrO-Ph 2-MeO-3-Pyr 8-Qnl CO H
2-62 4-nPrO-Ph 2-MeO-3-Pyr 8-Qnl NHCO Me
2-63 4-nPrO-Ph 2-MeO-3-Pyr 8-Qnl NMeCO H
2-64 4-F-Ph 2,3-diMe-Ph 1-Nap CO H
2-65 4-Cl-Ph 2,3-diMe-Ph 1-Nap CO H
2-66 3,4-Etdo-Ph 2,3-diMe-Ph 1-Nap CO H
2-67 3,4-Tmdo-Ph 2,3-diMe-Ph 1-Nap CO H
2-68 2,4-diMe-Ph 2,3-diMe-Ph 1-Nap CO H
2-69 2,4-diMeO-Ph 2,3-diMe-Ph 1-Nap CO H
2-70 2,5-diMeO-Ph 2,3-diMe-Ph 1-Nap CO H
2-71 4- (1-Imd) -Ph 3-CF ₃ -Ph 1-Nap CO H
2-72 4- (1-Imd) -Ph 3-CF ₃ -Ph 1-Nap NHCO Me
2-73 4- (1-Imd) -Ph 3-CF ₃ -Ph 1-Nap NMeCO H
2-74 4- (1-Imd) -Ph 2,3-diMe-Ph 1-Nap CO H
2-75 4- (1-Imd) -Ph 2,3-diMe-Ph 1-Nap NHCO Me
2-76 4- (1-Imd) -Ph 2,3-diMe-Ph 1-Nap NHCO Et
2-77 4- (1-Imd) -Ph 2,3-diMe-Ph 1-Nap NHCO nPr
2-78 4- (1-Imd) -Ph 2,3-diMe-Ph 1-Nap NHCO nBu
2-79 4- (1-Imd) -Ph 2,3-diMe-Ph 1-Nap NHCO nPn
2-80 4- (1-Imd) -Ph 2,3-diMe-Ph 1-Nap NHCO nHx
2-81 4- (1-Imd) -Ph 2,3-diMe-Ph 1-Nap NMeCO H
2-82 4- (1-Imd) -Ph 2,3-diMe-Ph 1-Nap NMeCO Me
2-83 4- (1-Imd) -Ph 2,3-diMe-Ph 1-Nap NEtCO H
2-84 4- (1-Imd) -Ph 2,3-diMe-Ph 1-Nap N (nPr) CO H
2-85 4- (1-Imd) -Ph 2,3-diMe-Ph 1-Nap N (nBu) CO H
2-86 4- (1-Imd) -Ph 2,3-diMe-Ph 1-Nap N (nPn) CO H
2-87 4- (1-Imd) -Ph 2,3-diMe-Ph 1-Nap N (nHx) CO H
2-88 4- (1-Imd) -Ph 2,3-diMe-Ph 4-Me-1-Nap CO H
2-89 4- (1-Imd) -Ph 2,3-diMe-Ph 4-Me-1-Nap NHCO Me
2-90 4- (1-Imd) -Ph 2,3-diMe-Ph 4-Me-1-Nap NMeCO H
2-91 4- (1-Imd) -Ph 2,3-diMe-Ph 5-Me-1-Nap CO H
2-92 4- (1-Imd) -Ph 2,3-diMe-Ph 5-Me-1-Nap NHCO Me
2-93 4- (1-Imd) -Ph 2,3-diMe-Ph 5-Me-1-Nap NMeCO H
2-94 4- (1-Imd) -Ph 2,3-diMe-Ph 4-MeNH-1-Nap CO H
2-95 4- (1-Imd) -Ph 2,3-diMe-Ph 4-MeNH-1-Nap NHCO Me
2-96 4- (1-Imd) -Ph 2,3-diMe-Ph 4-MeNH-1-Nap NMeCO H
2-97 4- (1-Imd) -Ph 2,3-diMe-Ph 5-MeNH-1-Nap CO H
2-98 4- (1-Imd) -Ph 2,3-diMe-Ph 5-MeNH-1-Nap NHCO Me
2-99 4- (1-Imd) -Ph 2,3-diMe-Ph 5-MeNH-1-Nap NMeCO H
2-100 4- (1-Imd) -Ph 2,3-diMe-Ph 4-Me ₂ N-1-Nap CO H
2-101 4- (1-Imd) -Ph 2,3-diMe-Ph 4-Me ₂ N-1-Nap NHCO Me
2-102 4- (1-Imd) -Ph 2,3-diMe-Ph 4-Me ₂ N-1-Nap NMeCO H
2-103 4- (1-Imd) -Ph 2,3-diMe-Ph 5-Me ₂ N-1-Nap CO H
2-104 4- (1-Imd) -Ph 2,3-diMe-Ph 5-Me ₂ N-1-Nap NHCO Me
2-105 4- (1-Imd) -Ph 2,3-diMe-Ph 5-Me ₂ N-1-Nap NMeCO H
2-106 4- (1-Imd) -Ph 2,3-diMe-Ph 4-Qnl CO H
2-107 4- (1-Imd) -Ph 2,3-diMe-Ph 4-Qnl NHCO Me
2-108 4- (1-Imd) -Ph 2,3-diMe-Ph 4-Qnl NMeCO H
2-109 4- (1-Imd) -Ph 2,3-diMe-Ph 5-Qnl CO H
2-110 4- (1-Imd) -Ph 2,3-diMe-Ph 5-Qnl NHCO Me
2-111 4- (1-Imd) -Ph 2,3-diMe-Ph 5-Qnl NMeCO H
2-112 4- (1-Imd) -Ph 2,3-diMe-Ph 8-Qnl CO H
2-113 4- (1-Imd) -Ph 2,3-diMe-Ph 8-Qnl CO Me
2-114 4- (1-Imd) -Ph 2,3-diMe-Ph 8-Qnl NHCO Me
2-115 4- (1-Imd) -Ph 2,3-diMe-Ph 8-Qnl NHCO Et
2-116 4- (1-Imd) -Ph 2,3-diMe-Ph 8-Qnl NHCO nPr
2-117 4- (1-Imd) -Ph 2,3-diMe-Ph 8-Qnl NHCO nBu
2-118 4- (1-Imd) -Ph 2,3-diMe-Ph 8-Qnl NHCO nPn
2-119 4- (1-Imd) -Ph 2,3-diMe-Ph 8-Qnl NHCO nHx
2-120 4- (1-Imd) -Ph 2,3-diMe-Ph 8-Qnl NMeCO H
2-121 4- (1-Imd) -Ph 2,3-diMe-Ph 8-Qnl NMeCO Me
2-122 4- (1-Imd) -Ph 2-Pyr 1-Nap CO H
2-123 4- (1-Imd) -Ph 3-Pyr 1-Nap CO H
2-124 4- (1-Imd) -Ph 4-Pyr 1-Nap CO H
2-125 4- (1-Imd) -Ph 6-MeO-2-Pyr 1-Nap CO H
2-126 4- (1-Imd) -Ph 2-MeO-3-Pyr 1-Nap CO H
2-127 4- (1-Imd) -Ph 2-MeO-3-Pyr 1-Nap CO Me
2-128 4- (1-Imd) -Ph 2-MeO-3-Pyr 1-Nap NHCO Me
2-129 4- (1-Imd) -Ph 2-MeO-3-Pyr 1-Nap NHCO Et
2-130 4- (1-Imd) -Ph 2-MeO-3-Pyr 1-Nap NHCO nPr
2-131 4- (1-Imd) -Ph 2-MeO-3-Pyr 1-Nap NHCO nBu
2-132 4- (1-Imd) -Ph 2-MeO-3-Pyr 1-Nap NHCO nPn
2-133 4- (1-Imd) -Ph 2-MeO-3-Pyr 1-Nap NHCO nHx
2-134 4- (1-Imd) -Ph 2-MeO-3-Pyr 1-Nap NMeCO H
2-135 4- (1-Imd) -Ph 2-MeO-3-Pyr 1-Nap NMeCO Me
2-136 4- (1-Imd) -Ph 2-MeO-3-Pyr 1-Nap NEtCO H
2-137 4- (1-Imd) -Ph 2-MeO-3-Pyr 1-Nap N (nPr) CO H
2-138 4- (1-Imd) -Ph 2-MeO-3-Pyr 1-Nap N (nBu) CO H
2-139 4- (1-Imd) -Ph 2-MeO-3-Pyr 1-Nap N (nPn) CO H
2-140 4- (1-Imd) -Ph 2-MeO-3-Pyr 1-Nap N (nHx) CO H
2-141 4- (1-Imd) -Ph 2-MeO-3-Pyr 4-Me-1-Nap CO H
2-142 4- (1-Imd) -Ph 2-MeO-3-Pyr 4-Me-1-Nap NHCO Me
2-143 4- (1-Imd) -Ph 2-MeO-3-Pyr 4-Me-1-Nap NMeCO H
2-144 4- (1-Imd) -Ph 2-MeO-3-Pyr 5-Me-1-Nap CO H
2-145 4- (1-Imd) -Ph 2-MeO-3-Pyr 5-Me-1-Nap NHCO Me
2-146 4- (1-Imd) -Ph 2-MeO-3-Pyr 5-Me-1-Nap NMeCO H
2-147 4- (1-Imd) -Ph 2-MeO-3-Pyr 4-MeNH-1-Nap CO H
2-148 4- (1-Imd) -Ph 2-MeO-3-Pyr 4-MeNH-1-Nap NHCO Me
2-149 4- (1-Imd) -Ph 2-MeO-3-Pyr 4-MeNH-1-Nap NMeCO H
2-150 4- (1-Imd) -Ph 2-MeO-3-Pyr 5-MeNH-1-Nap CO H
2-151 4- (1-Imd) -Ph 2-MeO-3-Pyr 5-MeNH-1-Nap NHCO Me
2-152 4- (1-Imd) -Ph 2-MeO-3-Pyr 5-MeNH-1-Nap NMeCO H
2-153 4- (1-Imd) -Ph 2-MeO-3-Pyr 4-Me ₂ N-1-Nap CO H
2-154 4- (1-Imd) -Ph 2-MeO-3-Pyr 4-Me ₂ N-1-Nap NHCO Me
2-155 4- (1-Imd) -Ph 2-MeO-3-Pyr 4-Me ₂ N-1-Nap NMeCO H
2-156 4- (1-Imd) -Ph 2-MeO-3-Pyr 5-Me ₂ N-1-Nap CO H
2-157 4- (1-Imd) -Ph 2-MeO-3-Pyr 5-Me ₂ N-1-Nap NHCO Me
2-158 4- (1-Imd) -Ph 2-MeO-3-Pyr 5-Me ₂ N-1-Nap NMeCO H
2-159 4- (1-Imd) -Ph 2-MeO-3-Pyr 4-Qnl CO H
2-160 4- (1-Imd) -Ph 2-MeO-3-Pyr 4-Qnl NHCO Me
2-161 4- (1-Imd) -Ph 2-MeO-3-Pyr 4-Qnl NMeCO H
2-162 4- (1-Imd) -Ph 2-MeO-3-Pyr 5-Qnl CO H
2-163 4- (1-Imd) -Ph 2-MeO-3-Pyr 5-Qnl NHCO Me
2-164 4- (1-Imd) -Ph 2-MeO-3-Pyr 5-Qnl NMeCO H
2-165 4- (1-Imd) -Ph 2-MeO-3-Pyr 8-Qnl CO H
2-166 4- (1-Imd) -Ph 2-MeO-3-Pyr 8-Qnl CO Me
2-167 4- (1-Imd) -Ph 2-MeO-3-Pyr 8-Qnl NHCO Me
2-168 4- (1-Imd) -Ph 2-MeO-3-Pyr 8-Qnl NHCO Et
2-169 4- (1-Imd) -Ph 2-MeO-3-Pyr 8-Qnl NHCO nPr
2-170 4- (1-Imd) -Ph 2-MeO-3-Pyr 8-Qnl NHCO nBu
2-171 4- (1-Imd) -Ph 2-MeO-3-Pyr 8-Qnl NHCO nPn
2-173 4- (1-Imd) -Ph 2-MeO-3-Pyr 8-Qnl NHCO nHx
2-174 4- (1-Imd) -Ph 2-MeO-3-Pyr 8-Qnl NMeCO H
2-175 4- (1-Imd) -Ph 2-MeO-3-Pyr 8-Qnl NMeCO Me
2-176 4- (1-Imd) -Ph 2-MeO-3-Pyr 8-Qnl NEtCO H
2-177 4- (1-Imd) -Ph 2-MeO-3-Pyr 8-Qnl N (nPr) CO H
2-178 4- (1-Imd) -Ph 2-MeO-3-Pyr 8-Qnl N (nBu) CO H
2-179 4- (1-Imd) -Ph 2-MeO-3-Pyr 8-Qnl N (nPn) CO H
2-180 4- (1-Imd) -Ph 2-MeO-3-Pyr 8-Qnl N (nHx) CO H
2-181 4- (1-Imd) -Ph 2-MeO-4-Pyr 1-Nap CO H
2-182 4- (1-Imd) -Ph 2-MeO-4-Pyr 1-Nap NHCO Me
2-183 4- (1-Imd) -Ph 2-MeO-4-Pyr 1-Nap NMeCO H
2-184 1-Nap 2,3-diMe-Ph 1-Nap CO H
2-185 1-Nap 2,3-diMe-Ph 1-Nap NHCO Me
2-186 1-Nap 2,3-diMe-Ph 1-Nap NMeCO H
2-187 2-Nap 2,3-diMe-Ph 1-Nap CO H
2-188 2-Nap 2,3-diMe-Ph 1-Nap NHCO Me
2-189 2-Nap 2,3-diMe-Ph 1-Nap NMeCO H
2-190 4-EtO-Ph 2,3-diMe-Ph 1-Nap NEtCO H
2-200 4-EtO-Ph 2,3-diMe-Ph 1-Nap N (nPr) CO H
2-201 4-EtO-Ph 2,3-diMe-Ph 8-Qnl NEtCO H
2-202 4-EtO-Ph 2,3-diMe-Ph 8-Qnl N (nPr) CO H
2-203 4-EtO-Ph 2-MeO-3-Pyr 1-Nap NEtCO H
2-204 4-EtO-Ph 2-MeO-3-Pyr 1-Nap N (nPr) CO H
2-205 4-EtO-Ph 2-MeO-3-Pyr 8-Qnl NEtCO H
2-206 4-EtO-Ph 2-MeO-3-Pyr 8-Qnl N (nPr) CO H
2-207 4- (1-Imd) -Ph 2,3-diMe-Ph 1-Nap NEtCO H
2-208 4- (1-Imd) -Ph 2,3-diMe-Ph 1-Nap N (nPr) CO H
2-209 4- (1-Imd) -Ph 2,3-diMe-Ph 1-Nap N (nBu) CO H
2-210 4- (1-Imd) -Ph 2,3-diMe-Ph 1-Nap N (nPn) CO H
2-211 4- (1-Imd) -Ph 2,3-diMe-Ph 1-Nap N (nHx) CO H
2-212 4- (1-Imd) -Ph 2,3-diMe-Ph 8-Qnl NEtCO H
2-213 4- (1-Imd) -Ph 2,3-diMe-Ph 8-Qnl N (nPr) CO H
2-214 4- (1-Imd) -Ph 2-MeO-3-Pyr 1-Nap NEtCO H
2-215 4- (1-Imd) -Ph 2-MeO-3-Pyr 1-Nap N (nPr) CO H
2-216 4- (1-Imd) -Ph 2-MeO-3-Pyr 1-Nap N (iPr) CO H
2-217 4- (1-Imd) -Ph 2-MeO-3-Pyr 1-Nap N (nBu) CO H
2-218 4- (1-Imd) -Ph 2-MeO-3-Pyr 1-Nap N (sBu) CO H
2-219 4- (1-Imd) -Ph 2-MeO-3-Pyr 1-Nap N (iBu) CO H
2-220 4- (1-Imd) -Ph 2-MeO-3-Pyr 1-Nap N (tBu) CO H
2-221 4- (1-Imd) -Ph 2-MeO-3-Pyr 1-Nap N (nPn) CO H
2-222 4- (1-Imd) -Ph 2-MeO-3-Pyr 1-Nap N (nHx) CO H
2-223 4- (1-Imd) -Ph 2-MeO-3-Pyr 8-Qnl NEtCO H
2-224 4- (1-Imd) -Ph 2-MeO-3-Pyr 8-Qnl N (nPr) CO H
￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣￣

In Tables 1 and 2, suitable compounds are:
Exemplified compound numbers 1-1, 1-4, 1-5, 1-6, 1-7, 1-9, 1-10, 1-12, 1-13, 1-14, 1-15, 1-16 , 1-17, 1-20, 1-21, 1-22, 1-23, 1-25, 1-30, 1-31, 1-32, 1-36, 1-37, 1-38, 1 -42, 1-44, 1-45, 1-46, 1-47, 1-48, 1-49, 1-52, 1-79, 1-83, 1-84, 1-87, 1-89 , 1-90, 1-91, 1-92, 1-93, 1-94, 1-95, 1-96, 1-99, 1-101, 1-102, 1-103, 1-104, 1 -107, 1-109, 1-110, 1-112, 1-114, 1-116, 1-117, 1-118, 1-119, 1-120, 1-123, 1-124, 1-125 , 1-126, 1-127, 1-128, 1-131, 1-132, 1-133, 1-134, 1-135, 1-138, 1-139, 1-140, 1-141, 1 -142, 1-143, 1-144, 1-145, 1-148, 1-149, 1-150, 1-151, 1-154, 1-157, 1-159, 1-160, 1-162 , 1-165, 1-168, 1-181, 1-182, 1-183, 1-185, 1-187, 1-188, 1-189, 1-190, 1-205, 1-206, 1 -207, 1-208, 1-210, 1-211, 1-212,1-216,1-218,1-220,1-221,1-222,1-223,1-225,1-226 , 1-227,1-228,1-229,1-230,1-231,1-249,1-254,1-255,1-256,1-257,1-258,1-259,1 -260, 1-261, 1-262, 1-263, 1-264 1-265, 1-266, 1-267, 1-268, 1-269, 1-271, 1-273, 1-274, 1-276, 1-277, 1-278, 1-279, 1- 280, 1-281, 1-282, 1-283, 1-284, 1-285, 1-286, 1-287, 1-288, 1-289, 1-291, 1-292, 1-293, 1-294,1-295,1-296,1-298,1-299,1-300,1-301,1-302,1-303,1-304,1-314,1-319,1- 321, 1-323, 1-325, 1-326, 1-327, 1-328, 1-331, 1-332, 1-333, 1-334, 1-333, 1-338, 1-351, 1-357, 1-359, 1-361, 1-363, 1-365, 1-371, 1-372, 1-373, 1-374, 1-375, 1-376, 1-377, 1- 378, 1-379, 1-381, 1-384, 1-385, 1-386, 1-387, 1-396, 1-404, 1-406, 1-407, 1-411, 1-413, 1-414, 1-415, 1-420, 1-421, 1-422, 1-424, 1-425, 1-426, 1-427, 1-428, 1-431, 1-432, 1- 436,1-437,1-438,1-439,1-440,1-441,1-442,1-474,1-475,1-477,1-482,1-505,1-522, 1-524, 1-525, 1-526, 1-559, 1-560, 1-561, 1-569, 1-575, 1-576, 1-577, 1-583, 1-584, 1- 588, 1-589, 1-591, 1-596, 1-599, 1-600, 1-604, 1-605, 1-607, 1-608, 1-609, 1-610, 1-611 1-612, 1-615, 1-616, 1-620, 1-621, 1-625, 1-626, 1-630, 1-631, 1-632, 1-633, 1-634, 1- 635, 1-636, 1-638, 1-639, 1-642, 1-643, 1-647, 1-648, 1-652, 1-653, 1-660, 1-661, 1-668, 1-669, 1-673, 1-674, 1-675, 1-676, 1-677, 1-678, 1-679, 1-680, 1-681, 1-682, 1-683, 1- 687, 1-688, 1-689, 1-691, 1-692, 1-695, 1-696, 1-698, 1-699, 1-700, 1-702, 1-703, 1-705, 1-706, 1-708, 1-709, 1-711, 1-712, 1-713, 1-714, 1-715, 1-719, 1-740, 1-750, 1-774, 1- 776, 1-777, 1-779, 1-780, 1-793, 1-802, 1-808, 1-833, 1-848, 1-872, 1-991, 1-992, 1-993, 1-994, 1-997, 1-998, 1-1003, 1-1004, 1-1005, 1-1012, 1-1016, 1-1019, 1-1020, 1-1022, 1-1027, 1- 1031, 1-1043, 1-1044, 1-1045, 1-1047, 1-1048, 1-1049, 1-1050, 1-1052, 1-1053, 1-1057, 1-1060, 1-1061, 1-1062, 1-1067, 1-1068, 1-1069, 1-1070, 1-1071, 1-1072, 1-1073, 1-1074, 1-1075, 1-1080, 1-1087, 1- 1088, 1-1092, 1-1093, 1-1094, 1-1096, 1-1097, 1-1098, 1-110 0, 1-1101, 1-1102, 1-1103, 1-1104, 1-1106, 1-1108, 1-1112, 1-1113, 1-1115, 1-1122, 1-1153, 1-1182, 1-1198, 2-2, 2-3, 2-5, 2-6, 2-7, 2-8, 2-23, 2-25, 2-64, 2-65, 2-66, 2- 67, 2-68, 2-69, 2-70, or 2-187, and a more preferable compound is
Illustrative compound numbers 1-23, 1-25, 1-32, 1-36, 1-38, 1-42, 1-44, 1-49, 1-109, 1-110, 1-112, 1-114 , 1-117, 1-118, 1-119, 1-123, 1-125, 1-127, 1-141, 1-144, 1-149, 1-150, 1-151, 1-154, 1 -168, 1-185, 1-187, 1-188, 1-216, 1-221, 1-222, 1-223, 1-225, 1-226, 1-229, 1-257, 1-258 , 1-268, 1-278, 1-285, 1-289, 1-304, 1-314, 1-338, 1-351, 1-357, 1-359, 1-361, 1-363, 1 -365,1-371,1-374,1-379,1-404,1-411,1-442,1-561,1-569,1-575,1-576,1-583,1-584 , 1-588, 1-589, 1-599, 1-600, 1-610, 1-615, 1-616, 1-620, 1-621, 1-626, 1-635, 1-638, 1 -642, 1-643, 1-652, 1-660, 1-668, 1-669, 1-683, 1-687, 1-688, 1-689, 1-691, 1-700, 1-719 , 1-740, 1-750, 1-776, 1-777, 1-779, 1-780, 1-793, 1-802, 1-808, 1-833, 1-848, 1-991, 1 -992, 1-993, 1-994, 1-998, 1-1004, 1-1005, 1-1012, 1-1019, 1-1022, 1-1027, 1-1031, 1-1043, 1-1044 , 1-1045, 1-1049, 1-1057, 1-1068, 1-1069, 1-1071, 1-1073, 1-1074, 1-1075, 1 -1080, 1-1088, 1-1092, 1-1093, 1-1097, 1-1101, 1-1115, or 1-1182, and more preferable compounds are
Illustrative compound numbers 1-25, 1-32, 1-38, 1-49, 1-110, 1-112, 1-114, 1-149, 1-154, 1-185, 1-223, 1-304 , 1-314, 1-361, 1-363, 1-379, 1-442, 1-561, 1-569, 1-583, 1-584, 1-588, 1-599, 1-600, 1 -615, 1-621, 1-626, 1-642, 1-652, 1-660, 1-669, 1-683, 1-688, 1-689, 1-719, 1-740, 1-776 , 1-777, 1-793, 1-802, 1-808, 1-833, 1-848, 1-991, 1-992, 1-993, 1-994, 1-1004, 1-1012, 1 -1019, 1-1031, 1-1043, 1-1044, 1-1045, 1-1075, 1-1080, 1-1093, 1-1097, 1-1101, or 1-1182 Suitable compounds are
Illustrative compound number 1-599: N- (4-acetylphenyl) -2- [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetamide,
Illustrative compound number 1-776: 1- [4- [2- [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetylamino] phenyl] -5-methyl-1H- Pyrazole-4-carboxylic acid ethyl ester,
Illustrative compound number 1-777: 1- [4- [2- [N- (2,3-dimethylphenyl) -N- (quinoline-8-sulfonyl) amino] acetylamino] phenyl] -5-methyl-1H- Pyrazole-4-carboxylic acid ethyl ester,
Exemplary Compound No. 1-793: 2- [N- (2,3-dimethylphenyl) -N- (naphthalen-1-sulfonyl) amino] -N- [4- (imidazol-1-yl) phenyl] acetamide, or Its monohydrochloride,
Illustrative compound number 1-802: 2- [N- (2,3-dimethylphenyl) -N- (4-fluoronaphthalene-1-sulfonyl) amino] -N- [4- (imidazol-1-yl) phenyl] Acetamide,
Illustrative compound number 1-808: 2- [N- (2,3-dimethylphenyl) -N- (quinolin-8-sulfonyl) amino] -N- [4- (imidazol-1-yl) phenyl] acetamide, or Its monohydrochloride or dihydrochloride,
Illustrative compound number 1-833: N- [4- (imidazol-1-yl) phenyl] -2- [N- (2-methoxypyridin-3-yl) -N- (naphthalene-1-sulfonyl) amino] acetamide ,
Illustrative compound number 1-848: N- [4- (imidazol-1-yl) phenyl] -2- [N- (2-methoxypyridin-3-yl) -N- (quinolin-8-sulfonyl) amino] acetamide ,
Illustrative compound number 1-991: N- [4- (4,5-dichloroimidazol-1-yl) phenyl] -2- [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) Amino] acetamide,
Illustrative compound number 1-992: N- [4- (4,5-dichloroimidazol-1-yl) phenyl] -2- [N- (2,3-dimethylphenyl) -N- (quinoline-8-sulfonyl) Amino] acetamide,
Illustrative compound number 1-993: 2- [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- [4- (1,3-oxazol-5-yl) phenyl ] Acetamide,
Illustrative compound number 1-994: 2- [N- (2,3-dimethylphenyl) -N- (quinolin-8-sulfonyl) amino] -N- [4- (1,3-oxazol-5-yl) phenyl ] Acetamide,
Illustrative compound number 1-1004: 2- [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- [4-([1,2,4] triazole-1- Yl) phenyl] acetamide,
Illustrative compound number 1-1012: 2- [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- [4-([1,2,3] thiadiazole-4- Yl) phenyl] acetamide,
Illustrative compound number 1-1043: 2- [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- [4- (4-methyl-5-thioxo-4,5 -Dihydro-1H- [1,2,4] triazol-3-yl) phenyl] acetamide,
Exemplified compound number 1-1044: 2- [N- (2,3-dimethylphenyl) -N- (4-fluoronaphthalene-1-sulfonyl) amino] -N- [4- (4-methyl-5-thioxo- 4,5-dihydro-1H- [1,2,4] triazol-3-yl) phenyl] acetamide,
Exemplified Compound No. 1-1045: 2- [N- (2,3-dimethylphenyl) -N- (quinoline-8-sulfonyl) amino] -N- [4- (4-methyl-5-thioxo-4,5 -Dihydro-1H- [1,2,4] triazol-3-yl) phenyl] acetamide, or
Exemplified compound number 1-1182: 2- [N- (2,3-dimethylphenyl) -N- (naphthalen-1-sulfonyl) amino] -N- [6- (morpholin-4-yl) pyridin-3-yl ] Acetamide compound.

The compound having the general formula (I) or the general formula (Ia) of the present invention can be produced according to the following methods A to N.

In the structural formulas of the compounds of Method A to Method N, A ¹ , A ² , A ³ , R ^1b , and R ² are as defined above, and R ⁴ , R ⁵ , R ⁶ , or , R ⁷ represents a hydrogen atom or a C ₁ -C ₆ alkyl group, and R ⁸ represents C ₁ -C ₆ alkoxy, amino, C ₁ -C ₆ alkylamino, or di (C ₁ -C ₆ alkyl) An amino group (the alkyl groups are the same or different), R ⁹ represents a C ₁ -C ₆ alkyl group, and R ¹⁰ represents an oxygen atom or a sulfur atom.

A ⁴ represents a phenyl group which may be substituted (the substituents are the same or different and represent 1 to 2 groups selected from the substituent group α);
A substituted phenyl group [the substituent is an essential phenyl group which may be substituted (the substituents are the same or different and represent one or two groups selected from the substituent group α)] And optionally represents the same or different and 1 to 2 groups selected from the substituent group α],
A substituted phenyl group [the substituent is an essential phenyl group which may be substituted (the substituents are the same or different and represent 1 to 3 groups selected from the substituent group α)] And optionally represents the same or different one group selected from the substituent group α],
A substituted phenyl group [the substituent is, as essential, a 4- to 8-membered group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom, which may be substituted] 1 represents a heterocyclyl group (the substituents are the same or different and represent 1 to 2 groups selected from the substituent group α), and are optionally the same or different and selected from the substituent group α. To 2 groups]
A substituted phenyl group [the substituent is, as essential, a 4- to 8-membered group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom, which may be substituted] A heterocyclyl group (the substituents are the same or different and represent 1 to 3 groups selected from the substituent group α), and are optionally the same or different and selected from the substituent group α; Number of groups],
Optionally substituted 5- to 6-membered aromatic heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom (the substituents may be the same or different, 1 to 2 groups selected from group α)
A substituted 5- to 6-membered aromatic heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom [the substituent is substituted as an essential one; Or a phenyl group (the substituents are the same or different and represent one or two groups selected from the substituent group α), and are optionally the same or different and selected from the substituent group α. 1 to 2 groups]
A substituted 5- to 6-membered aromatic heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom [the substituent is substituted as an essential one; Or a phenyl group (the substituents are the same or different and represent 1 to 3 groups selected from the substituent group α), and are optionally the same or different and selected from the substituent group α. Shows one group]
A substituted 5- to 6-membered aromatic heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom [the substituent is substituted as essential A 4- to 8-membered heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom (the substituents may be the same or different and selected from the substituent group α) And optionally represents the same or different and 1 to 2 groups selected from the substituent group α], or
A substituted 5- to 6-membered aromatic heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom [the substituent is substituted as an essential one; A 4- to 8-membered heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom (the substituents may be the same or different and selected from the substituent group α) And optionally represents the same or different and one group selected from the substituent group α].

X ¹ is a chloro group; a bromo group; an iodo group; a lower alkylsulfonyloxy group such as methanesulfonyloxy or ethanesulfonyloxy; a halogeno lower alkylsulfonyloxy group such as trifluoromethanesulfonyloxy; an aryl such as benzenesulfonyloxy A sulfonyloxy group; a lower alkylated arylsulfonyloxy group such as p-toluenesulfonyloxy; or a halogenoarylsulfonyloxy group such as p-chlorobezensulfonyloxy, preferably a chloro group, a bromo group or Iodo group.

X ² represents a chloro group, a bromo group or an iodo group, and preferably a bromo group or an iodo group.

In the reactions of the following methods A to N, when a compound serving as a reaction substrate has a group that inhibits a target reaction such as an amino group, a hydroxyl group, or a carboxyl group, a protective group for these groups is appropriately selected as necessary. May be introduced, and the introduced protecting group may be removed as necessary. The protecting group for the group that inhibits the target reaction is not particularly limited as long as it is a protecting group that is usually used for proceeding with the reaction.For example, Green, TH, Wuts, PGM, Protective Groups in Organic Synthesis It may be a protecting group described in Third Edition, 1999, John Wiley & Sons, Inc. The reaction for introducing these protecting groups and the reaction for removing the protecting groups can be carried out according to conventional methods (for example, the methods described in the above-mentioned documents).

(Method A)
Method A is a method for producing compound (Ib) in which R ¹ and R ^1a are groups having the formula —NHCO— and R ² is a hydrogen atom in formula (I). Method A is a method based on solid-phase synthesis. An appropriate resin for solid-phase synthesis is selected, the compound is desorbed from the resin at an appropriate stage, and an ordinary method [eg, encoding of IRORI, a Discovery Partners International Company] Synthesis method (URL:
Nicolaou, KC et al., Angew. Chem. Int. Ed. Engl., 1995, 34, p.2289; Nicolaou, KC et al., J. Am. Chem. Soc., 2000, Vol.122, p.9939-9976; “From Combinatorial Chemistry Introduction to Application”, Combinatorial Chemistry Study Group, Chemistry Dojin: “THE COMBINATORIAL INDEX”, Bunin, Barry A., ACADEMIC PRESS, etc.) . The following steps A-1 to A-5 can be performed without continuous purification on the resin, and the compound (Ib) is purified by purifying the compound released from the resin after the completion of the step A-5. ) Can be obtained. Method A can also be applied to the production of compounds having formula (Ia).
(Step A-1)
In step A-1, compound (2), which is known or easily obtained from a known compound, is bound to known resin (1) in the presence of a reducing agent and an acid to produce compound (3). It is a process.

  In the compound (2), a compound having an optionally substituted 5-thioxo-4.5-dihydro-1H-1,2,4-triazolyl group is disclosed in Kuecuekguezel, SG et al., Farmaco, 2002, Vol. 57, p.583-588; Kuecuekguezel, I. et al., Bioorganic. Med. Chem. Lett., 2001, 11, p.1703-1708; or Rollas, S. et al., 1993, p. It can be produced according to the method described in Volume 48, pages 308-309 or a method analogous thereto.

  The resin (1) used is not particularly limited as long as it is a resin having a formyl group. For example, 2- (3,5-dimethoxy-4-formylphenoxy) ethoxy-methylpolystyrene, 2- (4-formyl- 3-methoxyphenoxy) ethyl polystyrene, 2- (3,5-dimethoxy-4-formylphenoxy) ethyl polystyrene, (3-formylindolyl) acetamidomethylpolystyrene, 4- (4-formyl-3-methoxyphenoxy) butyryl Amide resin, formyl polystyrene, benzyloxybenzaldehyde polystyrene, preferably 2- (3,5-dimethoxy-4-formylphenoxy) ethoxy-methylpolystyrene or 2- (3,5-dimethoxy-4-formylphenoxy) ) Ethyl polystyrene.

  The reducing agent used is not particularly limited as long as it is a reducing agent used for the reductive amination reaction. For example, sodium borohydride, sodium triacetoxyborohydride, sodium cyanoborohydride, lithium borohydride Alkali metal borohydride, lithium aluminum hydride, aluminum hydride compounds such as lithium hydride triethoxide, or di (isobutyl) aluminum hydride, di (methoxyethoxy) aluminum sodium dihydride It can be an organoaluminum hydride compound, preferably an alkali metal borohydride, and more preferably sodium triacetoxyborohydride.

  The acid to be used is not particularly limited as long as it is an acid usually used in a reductive amination reaction. For example, organic acids such as acetic acid, propionic acid and trifluoroacetic acid, p-toluenesulfonic acid, camphorsulfonic acid , An organic sulfonic acid such as trifluoromethanesulfonic acid, or an inorganic acid such as phosphoric acid or hydrochloric acid, preferably an organic acid, and more preferably acetic acid.

  The solvent used is not particularly limited as long as it does not inhibit the reaction, does not dissolve the resin, and can be diffused appropriately. For example, aromatic hydrocarbons such as benzene, toluene, xylene; Halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, dichloroethane, chlorobenzene, dichlorobenzene; esters such as ethyl formate, ethyl acetate, propyl acetate, butyl acetate, diethyl carbonate; diethyl ether, diisopropyl ether Ethers such as ter, tetrahydrofuran, dioxane, dimethoxyethane, diethylene glycol dimethyl ether; methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, t- Butanol, isoamyl alcohol, diethylene glycol, Alcohols such as lysine, octanol, cyclohexanol, methyl cellosolve; nitriles such as acetonitrile, isobutyronitrile; formamide, N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2 Amides such as pyrrolidone, N-methylpyrrolidinone, hexamethylphosphorotriamide; sulfoxides such as dimethyl sulfoxide, sulfolane; organic acids such as acetic acid, propionic acid, trifluoroacetic acid; or a mixture thereof It is preferably an amide, an organic acid, or a mixture thereof, and more preferably N, N-dimethylformamide, N, N-dimethylacetamide, acetic acid, or a mixture thereof. When organic acids are used as a solvent, it is not necessary to add an organic acid as a reagent.

  The reaction can be performed as necessary in the presence of a dehydrating agent for removing water produced by the reaction. Examples of the dehydrating agent used include alkali metal sulfates such as sodium sulfate, sulfuric acid It can be an alkaline earth metal sulfate such as magnesium, preferably magnesium sulfate.

  While the reaction temperature varies depending on the solvent, starting material, reagent and the like, it is generally 20 to 150 ° C., preferably 50 to 120 ° C.

  While the reaction time varies depending on the solvent, starting materials, reagents, reaction temperature, etc., it is generally 30 minutes to 48 hours, preferably 1 to 24 hours.

After the completion of the reaction, the resin is removed with a solvent (preferably a reaction solvent, halogenated hydrocarbons, ethers, alcohols, amides, water, And a mixture thereof, and more preferably a reaction solvent, dichloromethane, tetrahydrofuran, methanol, N, N-dimethylformamide, water, or a mixture thereof), dried, and directly subjected to the next reaction Can be used for
(Step A-2)
The step A-2 is a step of reacting the compound (3) with a compound (4) that is known or easily obtained from a known compound, following the step A-1.

  The reaction can be carried out as necessary in the presence of a base, and the base used is, for example, an alkali metal carbonate such as lithium carbonate, sodium carbonate, potassium carbonate; lithium hydrogen carbonate, sodium hydrogen carbonate Alkali metal hydrogen carbonates such as potassium hydrogen carbonate; or N-methylmorpholine, triethylamine, tributylamine, diisopropylethylamine, dicyclohexylamine, N-methylpiperidine, pyridine, 4-pyrrolidinopyridine, picoline, 4- (N , N-dimethylamino) pyridine, organic bases such as 2,6-di (tert-butyl) -4-methylpyridine, quinoline, N, N-dimethylaniline, N, N-diethylaniline, suitable Are organic bases.

  The solvent used is not particularly limited as long as it does not inhibit the reaction, does not dissolve the resin, and can be diffused appropriately. For example, aliphatic hydrocarbons such as hexane and heptane; benzene, Aromatic hydrocarbons such as toluene and xylene; Halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, dichloroethane, chlorobenzene, dichlorobenzene; ethyl formate, ethyl acetate, propyl acetate, butyl acetate, diethyl carbonate Esters such as acetone, ketones such as methyl ethyl ketone, diethyl ketone; ethers such as diethyl ether, diisopropyl ether, tetrahydrofuran, dioxane, dimethoxyethane, diethylene glycol dimethyl ether; acetonitrile, isobutyronitrile Nito like Amides such as formamide, N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, N-methylpyrrolidinone, hexamethylphosphorotriamide; dimethyl sulfoxide, sulfolane and the like Or a mixture thereof, preferably an amide, a sulfoxide or a mixture thereof, more preferably N, N-dimethylformamide or N, N-dimethylacetamide.

  While the reaction temperature varies depending on the solvent, starting materials, reagents and the like, it is generally −20 to 100 ° C., preferably 0 to 50 ° C.

  While the reaction time varies depending on the solvent, starting materials, reagents, reaction temperature, etc., it is generally 30 minutes to 48 hours, preferably 1 to 24 hours.

After the completion of the reaction, the resin is removed with a solvent (preferably a reaction solvent, halogenated hydrocarbons, ethers, alcohols, amides, water, A mixture thereof, more preferably a reaction solvent, dichloromethane, tetrahydrofuran, methanol, N, N-dimethylformamide, or a mixture thereof), dried, and used as it is in the next reaction. can do.
(Step A-3)
The step A-3 is a step of reacting the compound (5) with a compound (6) that is known or easily obtained from a known compound, following the step A-2.

  The reaction can be carried out as necessary in the presence of a base, and the base used is, for example, an alkali metal carbonate such as lithium carbonate, sodium carbonate, potassium carbonate; lithium hydrogen carbonate, sodium hydrogen carbonate Alkali metal hydrogen carbonates such as potassium hydrogen carbonate; or N-methylmorpholine, triethylamine, tributylamine, diisopropylethylamine, dicyclohexylamine, N-methylpiperidine, pyridine, 4-pyrrolidinopyridine, picoline, 4- (N , N-dimethylamino) pyridine, organic bases such as 2,6-di (tert-butyl) -4-methylpyridine, quinoline, N, N-dimethylaniline, N, N-diethylaniline, suitable Are organic bases.

  The solvent used is not particularly limited as long as it does not inhibit the reaction, does not dissolve the resin, and can be diffused appropriately. For example, aliphatic hydrocarbons such as hexane and heptane; benzene, Aromatic hydrocarbons such as toluene and xylene; Halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, dichloroethane, chlorobenzene, dichlorobenzene; ethyl formate, ethyl acetate, propyl acetate, butyl acetate, diethyl carbonate Esters such as acetone, ketones such as methyl ethyl ketone, diethyl ketone; ethers such as diethyl ether, diisopropyl ether, tetrahydrofuran, dioxane, dimethoxyethane, diethylene glycol dimethyl ether; acetonitrile, isobutyronitrile Nito like Amides such as formamide, N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, N-methylpyrrolidinone, hexamethylphosphorotriamide; dimethyl sulfoxide, sulfolane and the like Sulfoxides; or a mixture thereof, preferably amides, sulfoxides or a mixture thereof, and more preferably dimethyl sulfoxide.

  While the reaction temperature varies depending on the solvent, starting materials, reagents and the like, it is generally 20 to 150 ° C., preferably 50 to 100 ° C.

  While the reaction time varies depending on the solvent, starting materials, reagents, reaction temperature, etc., it is generally 30 minutes to 48 hours, preferably 1 to 24 hours.

After the completion of the reaction, the resin is removed with a solvent (preferably a reaction solvent, halogenated hydrocarbons, ethers, alcohols, amides, water, A mixture thereof, more preferably a reaction solvent, dichloromethane, tetrahydrofuran, methanol, N, N-dimethylformamide, or a mixture thereof), dried, and used as it is in the next reaction. can do.
(Step A-4)
Step A-4 is a step of reacting compound (7) with compound (8) which is known or easily obtained from a known compound in the presence of a base, following step A-3.

  Examples of the base used include alkali metal carbonates such as lithium carbonate, sodium carbonate and potassium carbonate; alkali metal bicarbonates such as lithium hydrogen carbonate, sodium hydrogen carbonate and potassium hydrogen carbonate; or N-methylmorpholine. , Triethylamine, tributylamine, diisopropylethylamine, dicyclohexylamine, N-methylpiperidine, pyridine, 4-pyrrolidinopyridine, picoline, 4- (N, N-dimethylamino) pyridine, 2,6-di (tert-butyl)- Organic bases such as 4-methylpyridine, quinoline, N, N-dimethylaniline, N, N-diethylaniline; or mixtures thereof, preferably organic bases or mixtures thereof; More preferably, pyridine, 4- (N, N-dimethylamino) pyrid Or mixtures thereof.

  The solvent used is not particularly limited as long as it does not inhibit the reaction, does not dissolve the resin, and can be diffused appropriately. For example, aliphatic hydrocarbons such as hexane and heptane; benzene, Aromatic hydrocarbons such as toluene and xylene; Halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, dichloroethane, chlorobenzene, dichlorobenzene; ethyl formate, ethyl acetate, propyl acetate, butyl acetate, diethyl carbonate Esters such as acetone, ketones such as methyl ethyl ketone, diethyl ketone; ethers such as diethyl ether, diisopropyl ether, tetrahydrofuran, dioxane, dimethoxyethane, diethylene glycol dimethyl ether; acetonitrile, isobutyronitrile Nito like Amides such as formamide, N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, N-methylpyrrolidinone, hexamethylphosphorotriamide; dimethyl sulfoxide, sulfolane and the like Sulfoxides; N-methylmorpholine, triethylamine, tripropylamine, tributylamine, diisopropylethylamine, dicyclohexylamine, N-methylpiperidine, pyridine, 4-pyrrolidinopyridine, picoline, 4- (N, N-dimethylamino) pyridine, Organic bases such as 2,6-di (t-butyl) -4-methylpyridine, quinoline, N, N-dimethylaniline, N, N-diethylaniline; or mixtures thereof, preferably , Halogenated hydrocarbons, organic bases Other is a mixture thereof, more preferably a methylene chloride, pyridine or a mixture thereof.

  While the reaction temperature varies depending on the solvent, starting material, reagent and the like, it is generally −20 to 150 ° C., preferably 0 to 100 ° C.

  While the reaction time varies depending on the solvent, starting materials, reagents, reaction temperature, etc., it is generally 30 minutes to 48 hours, preferably 1 to 24 hours.

After the completion of the reaction, the resin is removed with a solvent (preferably a reaction solvent, halogenated hydrocarbons, ethers, alcohols, amides, water, A mixture thereof, more preferably a reaction solvent, dichloromethane, tetrahydrofuran, methanol, N, N-dimethylformamide, or a mixture thereof), dried, and used as it is in the next reaction. can do.
(Step A-5)
Step A-5 is a step of detaching the target compound (Ib) from the compound (9) in the presence of an acid.

  The acid used is not particularly limited as long as it is an acid usually used for the removal reaction of a substituted benzyl group on a nitrogen atom, and examples thereof include acetic acid, propionic acid, trifluoroacetic acid, and pentafluoropropionic acid. It can be an organic acid, an organic sulfonic acid such as p-toluenesulfonic acid, camphorsulfonic acid, trifluoromethanesulfonic acid, or an inorganic acid such as hydrochloric acid, hydrobromic acid, hydroiodic acid, phosphoric acid. Is an organic acid, more preferably trifluoroacetic acid.

  The solvent used is not particularly limited as long as it does not inhibit the reaction, does not dissolve the resin, and can be diffused appropriately. For example, aliphatic hydrocarbons such as hexane and heptane; benzene, Aromatic hydrocarbons such as toluene and xylene; Halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, dichloroethane, chlorobenzene, dichlorobenzene; ethyl formate, ethyl acetate, propyl acetate, butyl acetate, diethyl carbonate Esters such as acetone, methyl ethyl ketone, ketones such as diethyl ketone; ethers such as diethyl ether, diisopropyl ether, tetrahydrofuran, dioxane, dimethoxyethane, diethylene glycol dimethyl ether; methanol, ethanol , N-propanol, iso Alcohols such as propanol, n-butanol, isobutanol, t-butanol, isoamyl alcohol, diethylene glycol, glycerin, octanol, cyclohexanol, methyl cellosolve; acetonitrile, isobutyronitrile Nitriles such as: formamide, N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, N-methylpyrrolidinone, amides such as hexamethylphosphorotriamide; dimethyl sulfoxide, sulfolane Or a mixture thereof, preferably a halogenated hydrocarbon, an amide or a mixture thereof, and more preferably methylene chloride.

  While the reaction temperature varies depending on the solvent, starting material, reagent and the like, it is generally −20 to 150 ° C., preferably 0 to 100 ° C.

  While the reaction time varies depending on the solvent, starting materials, reagents, reaction temperature, etc., it is generally 30 minutes to 48 hours, preferably 1 to 24 hours.

After completion of the reaction, the target compound of this step is isolated from the reaction mixture according to a conventional method. For example, the resin is filtered off from the reaction mixture, and a solvent (preferably a reaction solvent, halogenated hydrocarbons, ethers, alcohols, amides, water, or a mixture thereof is more preferable. By washing with a reaction solvent, dichloromethane, tetrahydrofuran, methanol, N, N-dimethylformamide, or mixtures thereof, most preferably being a reaction solvent) and concentrating the filtrate under reduced pressure. The target compound is obtained. The obtained target compound can be further purified by a conventional method, for example, recrystallization, reprecipitation, or silica gel column chromatography, if necessary.

(Method B)
Method B is a method for producing a compound (Ib) in which, in formula (I), R ¹ is a group having the formula —NHCO—, and R ² is a hydrogen atom. Method B can also be applied to the production of a compound having the formula (Ia).
(Process B-1)
In step B-1, compound (6), which is known or easily obtained from a known compound, is reacted with compound (8) which is known or easily obtained from a known compound in the presence of a base. This is a step for producing compound (10).

B-1 process is performed in accordance with the method similar to A-4 process. After completion of the reaction, the target compound of this step is isolated from the reaction mixture according to a conventional method. For example, water and a solvent immiscible with water (for example, benzene, diethyl ether, ethyl acetate, etc.) are added to the reaction mixture to extract the target compound, the organic layer is washed with water, and a drying agent such as anhydrous magnesium sulfate is used. After drying, the target compound is obtained by distilling off the solvent. The obtained target compound can be further purified by a conventional method such as recrystallization, reprecipitation, or silica gel column chromatography, if necessary.
(Step B-2)
Step B-2
(Step B-2a): a step of reacting the compound (10) obtained in Step B-1 with a compound (11) that is known or easily obtained from a known compound in the presence of a base, and
(Step B-2b): The step comprises a step of producing the compound (12) by treating the compound obtained in the step B-2a with an acid.
(Step B-2a)
Examples of the base used include alkali metal carbonates such as lithium carbonate, sodium carbonate and potassium carbonate; alkali metal bicarbonates such as lithium hydrogen carbonate, sodium hydrogen carbonate and potassium hydrogen carbonate; or N-methylmorpholine. , Triethylamine, tributylamine, diisopropylethylamine, dicyclohexylamine, N-methylpiperidine, pyridine, 4-pyrrolidinopyridine, picoline, 4- (N, N-dimethylamino) pyridine, 2,6-di (tert-butyl)- It can be an organic base such as 4-methylpyridine, quinoline, N, N-dimethylaniline, N, N-diethylaniline, preferably an alkali metal carbonate or alkali metal bicarbonate, more preferably Is potassium carbonate, sodium carbonate or sodium bicarbonate A.

  The solvent used is not particularly limited as long as it does not inhibit the reaction and dissolves the starting materials to some extent. For example, aliphatic hydrocarbons such as hexane and heptane; aromatics such as benzene, toluene and xylene Group hydrocarbons; halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, dichloroethane, chlorobenzene, dichlorobenzene; esters such as ethyl formate, ethyl acetate, propyl acetate, butyl acetate, diethyl carbonate; acetone Ketones such as methyl ethyl ketone and diethyl ketone; ethers such as diethyl ether, diisopropyl ether, tetrahydrofuran, dioxane, dimethoxyethane and diethylene glycol dimethyl ether; nitriles such as acetonitrile and isobutyronitrile; Amides such as amide, N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, N-methylpyrrolidinone and hexamethylphosphorotriamide; Sulfoxides such as dimethyl sulfoxide and sulfolane; Alternatively, it may be a mixture thereof, preferably amides, sulfoxides or a mixture thereof, and more preferably N, N-dimethylformamide or N, N-dimethylacetamide.

  While the reaction temperature varies depending on the solvent, starting material, reagent and the like, it is generally 0 to 150 ° C., preferably 20 to 100 ° C.

  While the reaction time varies depending on the solvent, starting materials, reagents, reaction temperature, etc., it is generally 30 minutes to 48 hours, preferably 1 to 24 hours.

After completion of the reaction, the target compound of this step is isolated from the reaction mixture according to a conventional method. For example, water and a solvent immiscible with water (for example, benzene, diethyl ether, ethyl acetate, etc.) are added to the reaction mixture to extract the target compound, the organic layer is washed with water, and a drying agent such as anhydrous magnesium sulfate is used. After drying, the target compound is obtained by distilling off the solvent. The obtained target compound can be further purified by a conventional method such as recrystallization, reprecipitation, or silica gel column chromatography, if necessary.
(Step B-2b)
The acid used is, for example, an organic acid such as acetic acid, propionic acid, trifluoroacetic acid, pentafluoropropionic acid, an organic sulfonic acid such as p-toluenesulfonic acid, camphorsulfonic acid, trifluoromethanesulfonic acid, or It can be an inorganic acid such as hydrochloric acid, hydrobromic acid, hydroiodic acid or phosphoric acid, preferably an organic acid, more preferably trifluoroacetic acid.

  The solvent used is not particularly limited as long as it does not inhibit the reaction and dissolves the starting materials to some extent. For example, aliphatic hydrocarbons such as hexane and heptane; aromatics such as benzene, toluene and xylene Group hydrocarbons; halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, dichloroethane, chlorobenzene, dichlorobenzene; esters such as ethyl formate, ethyl acetate, propyl acetate, butyl acetate, diethyl carbonate; acetone Ketones such as methyl ethyl ketone and diethyl ketone; ethers such as diethyl ether, diisopropyl ether, tetrahydrofuran, dioxane, dimethoxyethane, diethylene glycol dimethyl ether; methanol, ethanol, n-propanol , Isopropanol n-butanol, isobutanol, t-butanol, isoamyl alcohol, diethylene glycol, glycerin, octanol, cyclohexanol, alcohols such as methyl cellosolve; nitriles such as acetonitrile and isobutyronitrile Amides such as formamide, N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, N-methylpyrrolidinone and hexamethylphosphorotriamide; sulfoxides such as dimethyl sulfoxide and sulfolane Or a mixture thereof, preferably an aromatic hydrocarbon, a halogenated hydrocarbon, or a mixture thereof, and more preferably methylene chloride.

  While the reaction temperature varies depending on the solvent, starting material, reagent and the like, it is generally −20 to 150 ° C., preferably 0 to 100 ° C.

  While the reaction time varies depending on the solvent, starting materials, reagents, reaction temperature, etc., it is generally 30 minutes to 48 hours, preferably 1 to 24 hours.

After completion of the reaction, the target compound of this step is isolated from the reaction mixture according to a conventional method. For example, water and a solvent immiscible with water (for example, benzene, diethyl ether, ethyl acetate, etc.) are added to the reaction mixture to extract the target compound, the organic layer is washed with water, and a drying agent such as anhydrous magnesium sulfate is used. After drying, the target compound is obtained by distilling off the solvent. The obtained target compound can be further purified by a conventional method such as recrystallization, reprecipitation, or silica gel column chromatography, if necessary. In addition, the target compound of this step can be used in the next reaction without purification.
(Step B-3)
In the step B-3, the compound (12) obtained in the step B-2 is reacted with a compound (2) which is known or easily obtained from a known compound in the presence of a condensing agent. In which R ¹ is a group having the formula —NHCO— and R ² is a hydrogen atom.

The condensing agent used is
(1) A combination of a phosphate ester such as diethyl phosphoryl cyanide and diphenyl phosphoryl azide and the following base;
(2) carbodiimides such as 1,3-dicyclohexylcarbodiimide, 1,3-diisopropylcarbodiimide, 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide (including hydrochloride); a combination of the above carbodiimides and the following bases A combination of the above carbodiimides and N-hydroxys such as N-hydroxysuccinimide, 1-hydroxybenzotriazole, 1-hydroxy-7-azabenzotriazole, N-hydroxy-5-norbornene-2,3-dicarboximide ;
(3) A combination of disulfides such as 2,2′-dipyridyl disulfide, 2,2′-dibenzothiazolyl disulfide and phosphines such as triphenylphosphine and tributylphosphine;
(4) Like N, N′-disuccinimidyl carbonate, diethyl pyrocarbonate, di-2-pyridyl carbonate, S, S′-bis (1-phenyl-1H-tetrazol-5-yl) dithiocarbonate Carbonates;
(5) Phosphonic chlorides such as N, N′-bis (2-oxo-3-oxazolidinyl) phosphonic chloride;
(6) N, N′-disuccinimidyl oxalate, N, N′-diphthalimidyl oxalate, N, N′-bis (5-norbornene-2,3-dicarboxyimidyl) oxalate, 1 , 1′-bis (benzotriazolyl) oxalate, 1,1′-bis (6-chlorobenzotriazolyl) oxalate, 1,1′-bis (6-trifluoromethylbenzotriazolyl) oxalate Oxalates;
(7) A combination of the phosphine and an azodicarboxylic acid ester such as diethyl azodicarboxylate, or an azodicarboxamide such as 1,1 ′-(azodicarbonyl) dipiperidine; A combination of the following bases:
(8) N-lower alkyl-5-arylisoxazolium-3′-sulfonates such as N-ethyl-5-phenylisoxazolium-3′-sulfonate;
(9) Diheteroaryl diselenides such as di-2-pyridyl diselenide;
(10) Arylsulfonyl triazolides such as p-nitrobenzenesulfonyl triazolide;
(11) 2-halogeno-1-lower alkylpyridinium halides such as 2-chloro-1-methylpyridinium iodide, 2-bromo-1-ethylpyridinium chloride;
(12) Imidazoles such as 1,1′-oxalyldiimidazole and N, N′-carbonyldiimidazole;
(13) 3-Lower alkyl-2-halogeno-benzothiazolium fluoroborates such as 3-ethyl-2-chloro-benzothiazolium fluoroborate;
(14) 3-lower alkyl-benzothiazole-2-thelones such as 3-methyl-benzothiazole-2-thelone;
(15) Phosphate such as phenyl dichlorophosphate, polyphosphate ester;
(16) halogenosulfonyl isocyanates such as chlorosulfonyl isocyanate;
(17) Halogenosilanes such as trimethylsilyl chloride and triethylsilyl chloride;
(18) A combination of a lower alkanesulfonyl halide such as methanesulfonyl chloride and the following base; or
(19) N, N, N ′, N′-tetra lower alkyl halogenoformamidium chlorides, such as N, N, N ′, N′-tetramethylchloroformamidium chloride, Carbodiimides or a combination of carbodiimides and N-hydroxys, more preferably 1,3-dicyclohexylcarbodiimide or 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide (including hydrochloride) and 1 -Hydroxybenzotriazole or 1-hydroxy-7-azabenzotriazole combination.

  The solvent used is not particularly limited as long as it does not inhibit the reaction and dissolves the starting materials to some extent. For example, aliphatic hydrocarbons such as hexane and heptane; aromatics such as benzene, toluene and xylene Group hydrocarbons; halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, dichloroethane, chlorobenzene, dichlorobenzene; esters such as ethyl formate, ethyl acetate, propyl acetate, butyl acetate, diethyl carbonate; acetone Ketones such as methyl ethyl ketone and diethyl ketone; ethers such as diethyl ether, diisopropyl ether, tetrahydrofuran, dioxane, dimethoxyethane and diethylene glycol dimethyl ether; nitriles such as acetonitrile and isobutyronitrile; Amides such as amide, N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, N-methylpyrrolidinone and hexamethylphosphorotriamide; Sulfoxides such as dimethyl sulfoxide and sulfolane; Alternatively, it may be a mixture thereof, preferably a halogenated hydrocarbon, an amide or a mixture thereof, more preferably N, N-dimethylformamide or N, N-dimethylacetamide.

  Examples of the base used include alkali metal carbonates such as lithium carbonate, sodium carbonate and potassium carbonate; alkali metal bicarbonates such as lithium hydrogen carbonate, sodium hydrogen carbonate and potassium hydrogen carbonate; or N-methylmorpholine. , Triethylamine, tributylamine, diisopropylethylamine, dicyclohexylamine, N-methylpiperidine, pyridine, 4-pyrrolidinopyridine, picoline, 4- (N, N-dimethylamino) pyridine, 2,6-di (tert-butyl)- It can be organic bases such as 4-methylpyridine, quinoline, N, N-dimethylaniline, N, N-diethylaniline, preferably organic bases, more preferably triethylamine, diisopropylethylamine or Pyridine.

  While the reaction temperature varies depending on the solvent, starting material, reagent and the like, it is generally −20 to 150 ° C., preferably 0 to 100 ° C.

  While the reaction time varies depending on the solvent, starting materials, reagents, reaction temperature, etc., it is generally 30 minutes to 48 hours, preferably 1 to 24 hours.

After completion of the reaction, the target compound of this step is isolated from the reaction mixture according to a conventional method. For example, water and a solvent immiscible with water (for example, benzene, diethyl ether, ethyl acetate, etc.) are added to the reaction mixture to extract the target compound, the organic layer is washed with water, and a drying agent such as anhydrous magnesium sulfate is used. After drying, the target compound is obtained by distilling off the solvent. The obtained target compound can be further purified by a conventional method such as recrystallization, reprecipitation, or silica gel column chromatography, if necessary.

(Method C)
Method C is a method for producing a compound (Ic) in which, in formula (I), R ¹ is a group having the formula —NR ^1b CO—, and R ² is a hydrogen atom. Method C can also be applied to the production of compounds having formula (Ia).
(Step C-1)
In step C-1, compound (13) which is known or easily obtained from a known compound is reacted with compound (4) which is known or easily obtained from a known compound in the presence of a base. This is a step for producing compound (14).

Step C-1 is performed according to the same method as step A-2. After completion of the reaction, the target compound of this step is isolated from the reaction mixture according to a conventional method. For example, water and a solvent immiscible with water (for example, benzene, diethyl ether, ethyl acetate, etc.) are added to the reaction mixture to extract the target compound, the organic layer is washed with water, and a drying agent such as anhydrous magnesium sulfate is used. After drying, the target compound is obtained by distilling off the solvent. The obtained target compound can be further purified by a conventional method such as recrystallization, reprecipitation, or silica gel column chromatography, if necessary.
(Step C-2)
In the step C-2, the compound (14) obtained in the step C-1 is reacted with the compound (10) obtained in the step B-1 in the presence of a base. In the formula (I), R ¹ is represented by the formula In this step, the compound (Ic) is a group having —NR ^1b CO— and R ² is a hydrogen atom.

Step C-2 is performed according to the same method as step B-2a.

(Method D)
Method D is a method for producing a compound (Id) in which R ¹ is a group having the formula —NR ^1b CO— in formula (I). Method D can also be applied to the production of a compound having the formula (Ia).
(Step D-1)
In step D-1, in the presence of a condensing agent, the compound (13) that is known or easily obtained from a known compound is reacted with the compound (15) that is known or easily obtained from a known compound. In this step, compound (16) is produced.

Step D-1 is performed according to the same method as step B-3.
(Step D-2)
In the step D-2, the compound (16) obtained in the step D-1 is reacted with the compound (10) obtained in the step B-1 in the presence of a base. In the formula (I), R ¹ is represented by the formula This is a step for producing a compound (Id) which is a group having —NR ^1b CO—.

Step D-2 is performed according to the same method as step B-2a.

(E method)
Method E is a method for producing a compound (Ie) in which R ² is a hydrogen atom in formula (I). Method E can also be applied to the production of compounds having formula (Ia).
(Step E-1)
Step E-1 is a compound (6) that is known or easily obtained from a known compound in the presence of a base. In this step, compound (18) is produced by reacting with the resulting compound (17).

  Examples of the base used include alkali metal carbonates such as lithium carbonate, sodium carbonate and potassium carbonate; alkali metal bicarbonates such as lithium hydrogen carbonate, sodium hydrogen carbonate and potassium hydrogen carbonate; or N-methylmorpholine. , Triethylamine, tributylamine, diisopropylethylamine, dicyclohexylamine, N-methylpiperidine, pyridine, 4-pyrrolidinopyridine, picoline, 4- (N, N-dimethylamino) pyridine, 2,6-di (tert-butyl)- It can be organic bases such as 4-methylpyridine, quinoline, N, N-dimethylaniline, N, N-diethylaniline, preferably organic bases, more preferably triethylamine or diisopropylethylamine. is there.

  The solvent used is not particularly limited as long as it does not inhibit the reaction and dissolves the starting materials to some extent. For example, aliphatic hydrocarbons such as hexane and heptane; aromatics such as benzene, toluene and xylene Group hydrocarbons; halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, dichloroethane, chlorobenzene, dichlorobenzene; esters such as ethyl formate, ethyl acetate, propyl acetate, butyl acetate, diethyl carbonate; acetone Ketones such as methyl ethyl ketone and diethyl ketone; ethers such as diethyl ether, diisopropyl ether, tetrahydrofuran, dioxane, dimethoxyethane and diethylene glycol dimethyl ether; nitriles such as acetonitrile and isobutyronitrile; Amides such as amide, N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, N-methylpyrrolidinone and hexamethylphosphorotriamide; Sulfoxides such as dimethyl sulfoxide and sulfolane; Alternatively, it may be a mixture thereof, preferably amides, sulfoxides or a mixture thereof, and more preferably N, N-dimethylformamide or N, N-dimethylacetamide.

  While the reaction temperature varies depending on the solvent, starting material, reagent and the like, it is generally 0 to 150 ° C., preferably 20 to 100 ° C.

  The reaction time varies depending on the solvent, starting materials, reagents, reaction temperature and the like, but is usually 30 minutes to 24 hours, and preferably 1 to 8 hours.

After completion of the reaction, the target compound of this step is isolated from the reaction mixture according to a conventional method. For example, water and a solvent immiscible with water (for example, benzene, diethyl ether, ethyl acetate, etc.) are added to the reaction mixture to extract the target compound, the organic layer is washed with water, and a drying agent such as anhydrous magnesium sulfate is used. After drying, the target compound is obtained by distilling off the solvent. The obtained target compound can be further purified by a conventional method such as recrystallization, reprecipitation, or silica gel column chromatography, if necessary.
(Step E-2)
In step E-2, compound (18) obtained in step E-1 is reacted with compound (8) which is known or easily obtained from a known compound in the presence of a base, and in formula (I) , R ² is a step for producing a compound (Ie) in which a hydrogen atom is present.

Step E-2 is performed according to the same method as step A-4. After completion of the reaction, the target compound of this step is isolated from the reaction mixture according to a conventional method. For example, water and a solvent immiscible with water (for example, benzene, diethyl ether, ethyl acetate, etc.) are added to the reaction mixture to extract the target compound, the organic layer is washed with water, and a drying agent such as anhydrous magnesium sulfate is used. After drying, the target compound is obtained by distilling off the solvent. The obtained target compound can be further purified by a conventional method such as recrystallization, reprecipitation, or silica gel column chromatography, if necessary.

(F method)
Method F is a method for producing a compound (Ie) in which R ² is a hydrogen atom in formula (I). Method F can also be applied to the production of a compound having the formula (Ia).
(Step F-1)
In step F-1, compound (6) which is known or easily obtained from a known compound is reacted with compound (19) which is known or easily obtained from a known compound in the presence of a base. In the compound (10), A ³ is a step of producing a compound (10a) in which A ³ is a 2,4-dinitrophenyl group.

Step F-1 is performed according to the same method as step A-4. After completion of the reaction, the target compound of this step is isolated from the reaction mixture according to a conventional method. For example, water and a solvent immiscible with water (for example, benzene, diethyl ether, ethyl acetate, etc.) are added to the reaction mixture to extract the target compound, the organic layer is washed with water, and a drying agent such as anhydrous magnesium sulfate is used. After drying, the target compound is obtained by distilling off the solvent. The obtained target compound can be further purified by a conventional method such as recrystallization, reprecipitation, or silica gel column chromatography, if necessary.
(Step F-2)
In the F-2 step, the compound (10a) obtained in the F-1 step is obtained in the C-1 step in the presence of a base, or is known or easily obtained from a known compound (17). In the compound (Ie), A ³ is a 2,4-dinitrophenyl group to produce a compound (If).

Step F-2 is performed according to the same method as step B-2a.
(Step F-3)
F-3 process
(Step F-3a): a step of treating the compound (If) obtained in Step F-2 with mercaptoacetic acid in the presence of a base, and
(Step F-3b): The step comprises the step of producing the compound (20) by treating the compound obtained in the step F-3a with hydrochloric acid.
(F-3a process)
Examples of the base used include alkali metal carbonates such as lithium carbonate, sodium carbonate and potassium carbonate; alkali metal bicarbonates such as lithium hydrogen carbonate, sodium hydrogen carbonate and potassium hydrogen carbonate; or N-methylmorpholine. , Triethylamine, tributylamine, diisopropylethylamine, dicyclohexylamine, N-methylpiperidine, pyridine, 4-pyrrolidinopyridine, picoline, 4- (N, N-dimethylamino) pyridine, 2,6-di (tert-butyl)- It can be organic bases such as 4-methylpyridine, quinoline, N, N-dimethylaniline, N, N-diethylaniline, preferably organic bases, more preferably triethylamine or diisopropylethylamine. is there.

  The solvent used is not particularly limited as long as it does not inhibit the reaction and dissolves the starting materials to some extent. For example, aliphatic hydrocarbons such as hexane and heptane; aromatics such as benzene, toluene and xylene Group hydrocarbons; halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, dichloroethane, chlorobenzene, dichlorobenzene; esters such as ethyl formate, ethyl acetate, propyl acetate, butyl acetate, diethyl carbonate; acetone Ketones such as methyl ethyl ketone and diethyl ketone; ethers such as diethyl ether, diisopropyl ether, tetrahydrofuran, dioxane, dimethoxyethane and diethylene glycol dimethyl ether; nitriles such as acetonitrile and isobutyronitrile; Amides such as amide, N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, N-methylpyrrolidinone and hexamethylphosphorotriamide; Sulfoxides such as dimethyl sulfoxide and sulfolane; Alternatively, it may be a mixture thereof, preferably an aromatic hydrocarbon, a halogenated hydrocarbon, or a mixture thereof, more preferably methylene chloride.

  While the reaction temperature varies depending on the solvent, starting material, reagent and the like, it is generally −20 to 150 ° C., preferably 0 to 100 ° C.

  While the reaction time varies depending on the solvent, starting materials, reagents, reaction temperature, etc., it is generally 30 minutes to 48 hours, preferably 1 to 24 hours.

After completion of the reaction, the target compound of this step is isolated from the reaction mixture according to a conventional method. For example, water and a solvent immiscible with water (for example, benzene, diethyl ether, ethyl acetate, etc.) are added to the reaction mixture to extract the target compound, the organic layer is washed with water, and a drying agent such as anhydrous magnesium sulfate is used. After drying, the target compound is obtained by distilling off the solvent. The obtained target compound can be further purified by a conventional method such as recrystallization, reprecipitation, or silica gel column chromatography, if necessary. Moreover, the target compound of this process can be used for F-3b process, without refine | purifying, or can be used for F-4 process, without passing through F-3b process.
(F-3b process)
The solvent used is not particularly limited as long as it does not inhibit the reaction and dissolves the starting materials to some extent. For example, aliphatic hydrocarbons such as hexane and heptane; aromatics such as benzene, toluene and xylene Group hydrocarbons; halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, dichloroethane, chlorobenzene, dichlorobenzene; esters such as ethyl formate, ethyl acetate, propyl acetate, butyl acetate, diethyl carbonate; acetone Ketones such as methyl ethyl ketone and diethyl ketone; ethers such as diethyl ether, diisopropyl ether, tetrahydrofuran, dioxane, dimethoxyethane, diethylene glycol dimethyl ether; methanol, ethanol, n-propanol , Isopropanol n-butanol, isobutanol, t-butanol, isoamyl alcohol, diethylene glycol, glycerin, octanol, cyclohexanol, alcohols such as methyl cellosolve; nitriles such as acetonitrile and isobutyronitrile Amides such as formamide, N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, N-methylpyrrolidinone and hexamethylphosphorotriamide; sulfoxides such as dimethyl sulfoxide and sulfolane Or mixtures thereof, preferably esters, ethers or mixtures thereof, more preferably ethyl acetate or dioxane.

  While the reaction temperature varies depending on the solvent, starting material, reagent and the like, it is generally −20 to 150 ° C., preferably 0 to 100 ° C.

  While the reaction time varies depending on the solvent, starting materials, reagents, reaction temperature and the like, it is generally 5 minutes to 12 hours, preferably 10 minutes to 2 hours.

After completion of the reaction, the target compound of this step can be used in Step F-4 without purification.
(Step F-4)
In step F-4, in the presence of a base, compound (20) obtained in step F-3 is reacted with compound (8) that is known or easily obtained from a known compound, and in formula (I) , R ² is a step for producing a compound (Ie) in which a hydrogen atom is present.

Step F-4 is performed according to the same method as step A-4. After completion of the reaction, the target compound of this step is isolated from the reaction mixture according to a conventional method. For example, water and a solvent immiscible with water (for example, benzene, diethyl ether, ethyl acetate, etc.) are added to the reaction mixture to extract the target compound, the organic layer is washed with water, and a drying agent such as anhydrous magnesium sulfate is used. After drying, the target compound is obtained by distilling off the solvent. The obtained target compound can be further purified by a conventional method such as recrystallization, reprecipitation, or silica gel column chromatography, if necessary.

(G method)
Method G is a method for producing compound (Ii) in which A ¹ in formula (I) is a group having the formula -A ⁴ -CONR ⁵ R ⁶ . Method G can also be applied to the production of compounds having formula (Ia).
(Step G-1)
In step (G-1), compound (Ig) in which formula (I) is a group in which A ¹ is a group having formula -A ⁴ -COO (t-Bu) is treated with an acid, and in formula (I), In this step, A ¹ is a compound (Ih) which is a group having the formula —A ⁴ —COOH.

Compound (Ig) may be prepared by Method A or Method B using Compound (2a) in which A ¹ is a group having the formula -A ⁴ -COO (t-Bu) in Compound (2), or In 13), it can be produced by Method C or Method D using compound (13a) in which A ¹ is a group having the formula -A ⁴ -COO (t-Bu).

G-1 process is performed in accordance with the method similar to B-2b process.
(Step G-2)
In the step G-2, in the presence of a condensing agent, the compound (Ih) obtained in the step G-1 is reacted with a compound (21) which is known or can be easily obtained from a known compound, to give a compound of formula (I) Wherein A ¹ is a group having the formula -A ⁴ -CONR ⁵ R ⁶ .

  The condensing agent used is the same as in step B-3, and may be preferably carbodiimides, a combination of carbodiimides and N-hydroxys or imidazoles, and more preferably 1-ethyl-3- A combination of (3-dimethylaminopropyl) carbodiimide (including hydrochloride) and 1-hydroxybenzotriazole or 1-hydroxy-7-azabenzotriazole, or N, N′-carbonyldiimidazole.

  The solvent used is not particularly limited as long as it does not inhibit the reaction and dissolves the starting materials to some extent. For example, aliphatic hydrocarbons such as hexane and heptane; aromatics such as benzene, toluene and xylene Group hydrocarbons; halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, dichloroethane, chlorobenzene, dichlorobenzene; esters such as ethyl formate, ethyl acetate, propyl acetate, butyl acetate, diethyl carbonate; acetone Ketones such as methyl ethyl ketone and diethyl ketone; ethers such as diethyl ether, diisopropyl ether, tetrahydrofuran, dioxane, dimethoxyethane and diethylene glycol dimethyl ether; nitriles such as acetonitrile and isobutyronitrile; Amides such as amide, N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, N-methylpyrrolidinone and hexamethylphosphorotriamide; Sulfoxides such as dimethyl sulfoxide and sulfolane; Or a mixture thereof, preferably halogenated hydrocarbons, ethers, amides or mixtures thereof, more preferably methylene chloride, tetrahydrofuran, N, N-dimethylformamide or A mixture of them.

  While the reaction temperature varies depending on the solvent, starting material, reagent and the like, it is generally −20 to 150 ° C., preferably 0 to 100 ° C.

  The reaction time varies depending on the solvent, starting materials, reagents, reaction temperature and the like, but is usually 30 minutes to 24 hours, and preferably 1 to 8 hours.

After completion of the reaction, the target compound of this step is isolated from the reaction mixture according to a conventional method. For example, water and a solvent immiscible with water (for example, benzene, diethyl ether, ethyl acetate, etc.) are added to the reaction mixture to extract the target compound, the organic layer is washed with water, and a drying agent such as anhydrous magnesium sulfate is used. After drying, the target compound is obtained by distilling off the solvent. The obtained target compound can be further purified by a conventional method such as recrystallization, reprecipitation, or silica gel column chromatography, if necessary.

(Method H)
Method H is a compound in which, in formula (I), A ¹ is a group having the formula —A ⁴ —C (R ⁵ ) ═NOR ⁶ , and R ¹ is a group having the formula —NR ^1b CO— ( Ik). Method H can also be applied to the production of a compound having the formula (Ia).
(Process H-1)
Step H-1 is a compound in which, in the presence of a base, in formula (I), A ¹ is a group having the formula —A ⁴ —COR ⁵ , and R ¹ is a group having —NR ^1b CO— ( Ij) is reacted with compound (22) which is known or can be easily obtained from known compounds, and in formula (I), A ¹ has the formula -A ⁴ -C (R ⁵ ) = NOR ⁶ This is a step for producing a compound (Ik) which is a group and R ¹ is a group having the formula —NR ^1b CO—.

Compound (Ij), in the compounds (2), A ¹ is the A method or B method using compounds is a group having the formula -A ⁴ -COR ⁵ and (2b), or, in the compound (13), A ¹ can be produced by Method C or Method D using compound (13b), which is a group having the formula -A ⁴ -COR ⁵ .

  Examples of the base used include alkali metal carbonates such as lithium carbonate, sodium carbonate and potassium carbonate; alkali metal hydrogen carbonates such as lithium hydrogen carbonate, sodium hydrogen carbonate and potassium hydrogen carbonate; sodium acetate and potassium acetate. Organic acid metal salts; or N-methylmorpholine, triethylamine, tributylamine, diisopropylethylamine, dicyclohexylamine, N-methylpiperidine, pyridine, 4-pyrrolidinopyridine, picoline, 4- (N, N-dimethylamino) pyridine It may be an organic base such as 2,6-di (tert-butyl) -4-methylpyridine, quinoline, N, N-dimethylaniline, N, N-diethylaniline, preferably an organic acid metal salt Or organic bases, more preferably sodium acetate or vinegar It is potassium.

  The solvent used is not particularly limited as long as it does not inhibit the reaction and dissolves the starting materials to some extent. For example, aliphatic hydrocarbons such as hexane and heptane; aromatics such as benzene, toluene and xylene Group hydrocarbons; halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, dichloroethane, chlorobenzene, dichlorobenzene; esters such as ethyl formate, ethyl acetate, propyl acetate, butyl acetate, diethyl carbonate; acetone Ketones such as methyl ethyl ketone and diethyl ketone; ethers such as diethyl ether, diisopropyl ether, tetrahydrofuran, dioxane, dimethoxyethane, diethylene glycol dimethyl ether; methanol, ethanol, n-propanol , Isopropanol n-butanol, isobutanol, t-butanol, isoamyl alcohol, diethylene glycol, glycerin, octanol, cyclohexanol, alcohols such as methyl cellosolve; nitriles such as acetonitrile and isobutyronitrile Amides such as formamide, N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, N-methylpyrrolidinone and hexamethylphosphorotriamide; sulfoxides such as dimethyl sulfoxide and sulfolane Or mixtures thereof, preferably ethers, nitriles or mixtures thereof, more preferably dioxane or acetonitrile.

  While the reaction temperature varies depending on the solvent, starting materials, reagents and the like, it is generally 0 to 200 ° C., preferably 20 to 120 ° C.

  While the reaction time varies depending on the solvent, starting materials, reagents, reaction temperature, etc., it is generally 30 minutes to 48 hours, preferably 1 to 24 hours.

After completion of the reaction, the target compound of this step is isolated from the reaction mixture according to a conventional method. For example, water and a solvent immiscible with water (for example, benzene, diethyl ether, ethyl acetate, etc.) are added to the reaction mixture to extract the target compound, the organic layer is washed with water, and a drying agent such as anhydrous magnesium sulfate is used. After drying, the target compound is obtained by distilling off the solvent. The obtained target compound can be further purified by a conventional method such as recrystallization, reprecipitation, or silica gel column chromatography, if necessary.

(Method I)
Method I is a compound (Il) in which in Formula (I), A ¹ is a group having the formula —A ⁴ —C (OH) R ⁵ , and R ¹ is a group having the formula —NR ^1b CO—. It is a method of manufacturing. Method I can also be applied to the preparation of compounds having formula (Ia).
(Step I-1)
Step I-1 is a reduction of compound (Ij) in formula (I), wherein A ¹ is a group having the formula —A ⁴ —COR ⁵ and R ¹ is a group having —NR ^1b CO—. A compound (A) in which, in the formula (I), A ¹ is a group having the formula —A ⁴ —C (OH) R ⁵ and R ¹ is a group having the formula —NR ^1b CO—. Il).

  The reducing agent used is, for example, an alkali metal borohydride such as sodium borohydride, sodium triacetoxyborohydride, lithium borohydride; hydrogen such as lithium aluminum hydride, lithium triethoxide aluminum hydride Aluminum hydride compounds; sodium tellurium hydride; organoaluminum hydride compounds such as di (isobutyl) aluminum hydride, di (methoxyethoxy) aluminum sodium dihydride; and Lewis acids such as aluminum chloride, tin tetrachloride and titanium tetrachloride A combination of hydrogenated silyl compounds such as hydrogenated triethylsilane and hydrogenated triphenylsilane; or a radical initiator used as a catalyst such as azobisisobutyronitrile and triphenylboron and tributyltin hydride Hydrogenated triphenyltin may be a combination of a radical reducing agent such as hydrogenated dibutyltin preferably an alkali metal borohydride, more preferably sodium borohydride.

  The solvent used is not particularly limited as long as it does not inhibit the reaction and dissolves the starting materials to some extent. For example, aliphatic hydrocarbons such as hexane and heptane; aromatics such as benzene, toluene and xylene Group hydrocarbons: halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, dichloroethane, chlorobenzene, dichlorobenzene; such as diethyl ether, diisopropyl ether, tetrahydrofuran, dioxane, dimethoxyethane, diethylene glycol dimethyl ether Ethers: methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, t-butanol, isoamyl alcohol, diethylene glycol, glycerin, octanol, Cyclohexanol, meth Alcohols such as cellosolve; amides such as formamide, N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, N-methylpyrrolidinone, hexamethylphosphorotriamide; dimethyl A sulfoxide such as sulfoxide, sulfolane; or a mixture thereof, preferably an ether, an alcohol or a mixture thereof, more preferably methanol, ethanol, tetrahydrofuran or the like. It is a mixture of

  While the reaction temperature varies depending on the solvent, starting material, reagent and the like, it is generally −50 to 150 ° C., preferably 0 to 100 ° C.

  The reaction time varies depending on the solvent, starting materials, reagents, reaction temperature and the like, but is usually 30 minutes to 24 hours, and preferably 1 to 8 hours.

  Further, this step is carried out in the presence of a catalyst such as palladium-carbon and palladium hydroxide-carbon, platinum, Raney-nickel and the like (preferably in the presence of palladium-carbon) in a solvent (for example, methanol- , Alcohols such as ethanol, ethers such as tetrahydrofuran and dioxane, lower fatty acids such as acetic acid, or mixtures thereof with water, preferably in alcohols. ), Catalytic reduction at 0 to 100 ° C. (preferably 20 to 60 ° C.) in a hydrogen atmosphere.

After completion of the reaction, the target compound of this step is isolated from the reaction mixture according to a conventional method. For example, water and a solvent immiscible with water (for example, benzene, diethyl ether, ethyl acetate, etc.) are added to the reaction mixture to extract the target compound, the organic layer is washed with water, and a drying agent such as anhydrous magnesium sulfate is used. After drying, the target compound is obtained by distilling off the solvent. The obtained target compound can be further purified by a conventional method such as recrystallization, reprecipitation, or silica gel column chromatography, if necessary.

(J method)
The method J is a method for producing a compound (Io) in which, in the formula (I), A ¹ is a group having the formula —A ⁴ —OCH ₂ COR ⁸ . Method J can also be applied to the production of a compound having the formula (Ia).
(Step J-1)
In step J-1, compound (Im) in which A ¹ is a group having the formula -A ⁴ -OCH ₂ COO (t-Bu) in formula (I) is treated with an acid to give formula (I) Wherein A ¹ is a group having the formula —A ⁴ —OCH ₂ COOH.

Compound (Im), in the compounds (2), A ¹ is the A method or B method using formula _{^{-A 4 -OCH 2 COO (t-}} Bu) compound is a group having a (2c) or, In Compound (13), A ¹ can be produced by Method C or Method D using Compound (13c), which is a group having the formula —A ⁴ —OCH ₂ COO (t-Bu). In addition, compound (2c) and compound (13c) are prepared according to Renodon-Corniere, A. et al., J. Med. Chem., 2002, Vol. 45, No. 4, p. 944-954; et al., Chem. Pharm. Bull., 1999, 47, p.1685-1693; Asagarasu, A. et. al., Chem. Pharm. Bull., 1998, 46, p. 867-870; or according to the method described in Asagarasu, A. et. Al., Chem. Pharm. Bull., 1998, Vol. 46, p.697-703 or a method analogous thereto. it can.

Step J-1 is performed according to the same method as step B-2b.
(Step J-2)
In the step J-2, in the presence of a condensing agent, the compound (In) obtained in the step G-1 is reacted with a compound (23) which is known or can be easily obtained from a known compound, to obtain a compound of formula (I) In which A ¹ is a group having the formula —A ⁴ —OCH ₂ COR ⁸ (Io).

The J-2 process is performed according to the same method as the G-2 process.

(K method)
Method K is a method for producing a compound (Iq) or (Ir) in which, in formula (I), A ¹ is a group having the formula -A ⁴ -SOR ⁹ or -A ⁴ -SO ₂ R ⁹ . Method K can also be applied to the production of compounds having formula (Ia).
(Step K-1)
In step K-1, compound (Ip) in which A ¹ is a group having the formula -A ⁴ -SR ⁹ in formula (I) is oxidized with an oxidizing agent, and in formula (I), A ¹ is , A step of producing a compound (Iq) which is a group having the formula -A ⁴ -SOR ⁹ .

Compound (Ip), in the compounds (2), A ¹ is the A method or B method using compounds is a group having the formula -A ⁴ -SR ⁹ a (2d), or, in the compound (13), It can be produced by Method C or Method D using compound (13d) in which A ¹ is a group having the formula -A ⁴ -SR ⁹ .

  The oxidizing agent used is not particularly limited as long as it is usually used for the oxidation reaction of alkylsulfonyl groups. For example, organic peracids such as m-chloroperbenzoic acid and perphthalic acid, organic peracids and the like. Combinations with inorganic base compounds such as sodium hydrogen carbonate and potassium hydrogen carbonate; radicals such as 2,2,6,6-tetramethyl-1-piperidinyloxy-free radical (TEMPO); N-chlorosuccinimide A combination of succinimides such as N-bromosuccinimide and a perchloric acid such as perchloric acid; periodic acids such as sodium periodate; a hydrogen peroxide solution, a combination of hydrogen peroxide solution and acetic acid; Persulfate compounds such as Oxone (registered trademark), potassium persulfate, sodium persulfate; tetraisopropoxy titanium, tetraisopropoxy titanium Combination with 1,2-diphenyl-1,2-ethanediol; can be oxiranes such as dimethyldioxirane, preferably organic peracids or periodic acids, more preferably m-chloro Perbenzoic acid or sodium periodate.

  The amount of the oxidizing agent used is 0.5 to 1.5 mol, preferably 0.8 to 1.2 mol, more preferably, 1 mol of compound (Ip). 1.0 mole.

  The solvent used is not particularly limited as long as it does not inhibit the reaction and dissolves the starting materials to some extent. For example, aliphatic hydrocarbons such as hexane and heptane; aromatics such as benzene, toluene and xylene Group hydrocarbons; halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, dichloroethane, chlorobenzene, dichlorobenzene; esters such as ethyl formate, ethyl acetate, propyl acetate, butyl acetate, diethyl carbonate; acetone Ketones such as methyl ethyl ketone and diethyl ketone; ethers such as diethyl ether, diisopropyl ether, tetrahydrofuran, dioxane, dimethoxyethane, diethylene glycol dimethyl ether; methanol, ethanol, n-propanol , Isopropanol n-butanol, isobutanol, t-butanol, isoamyl alcohol, diethylene glycol, glycerin, octanol, cyclohexanol, alcohols such as methyl cellosolve; nitriles such as acetonitrile and isobutyronitrile Amides such as formamide, N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, N-methylpyrrolidinone and hexamethylphosphorotriamide; sulfoxides such as dimethyl sulfoxide and sulfolane Water; or mixtures thereof, preferably halogenated hydrocarbons, ethers, water, or mixtures thereof, more preferably methylene chloride, tetrahydrofuran, water, Or a mixture thereof.

  While the reaction temperature varies depending on the solvent, starting material, reagent and the like, it is generally 0 to 150 ° C., preferably 20 to 100 ° C.

  While the reaction time varies depending on the solvent, starting materials, reagents, reaction temperature, etc., it is generally 30 minutes to 48 hours, preferably 1 to 24 hours.

After completion of the reaction, the target compound of this step is isolated from the reaction mixture according to a conventional method. For example, water and a solvent immiscible with water (for example, benzene, diethyl ether, ethyl acetate, etc.) are added to the reaction mixture to extract the target compound, the organic layer is washed with water, and a drying agent such as anhydrous magnesium sulfate is used. After drying, the target compound is obtained by distilling off the solvent. The obtained target compound can be further purified by a conventional method such as recrystallization, reprecipitation, or silica gel column chromatography, if necessary.
(Step K-2)
In step K-2, compound (Iq) obtained in step K-1 is oxidized with an oxidizing agent, and in formula (I), A ¹ is a group having the formula —A ⁴ —SO ₂ R ^9. In this step, compound (Ir) is produced.

Step K-2 is performed according to the same method as step K-1. The amount of the oxidizing agent used is 1.0 to 10 mol, preferably 2.0 to 8.0 mol, and more preferably 4. mol per 1 mol of compound (Iq). 0 to 6.0 moles.

(L method)
The method L is a method for producing a compound (It) in which A ¹ in formula (I) is A ⁴ having a tetrazolyl group. Method L can also be applied to the production of compounds having formula (Ia).
(L-1 process)
In step L-1, compound (Is) in which formula (I) is a group in which A ¹ is a group having formula -A ⁴ -CN is treated with a nitrogen-containing reagent, and in formula (I), A ¹ is And a step of producing a compound (It) which is A ⁴ having a tetrazolyl group.

Compound (Is), in the compounds (2), A ¹ is the A method or B method using compounds is a group having the formula -A ⁴ -CN and (2e), or, in the compound (13), A ¹ can be produced by Method C or Method D using compound (13e), which is a group having the formula -A ⁴ -CN.

  The nitrogen-containing reagent used may be, for example, sodium azide, a combination of sodium azide and an inorganic chlorine compound such as ammonium chloride, a tin azide compound such as trimethyltin azide, tributyltin azide, etc. Is a combination of sodium azide and an inorganic chlorine compound such as ammonium chloride.

  The solvent used is not particularly limited as long as it does not inhibit the reaction and dissolves the starting materials to some extent. For example, aliphatic hydrocarbons such as hexane and heptane; aromatics such as benzene, toluene and xylene Group hydrocarbons; halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, dichloroethane, chlorobenzene, dichlorobenzene; esters such as ethyl formate, ethyl acetate, propyl acetate, butyl acetate, diethyl carbonate; acetone Ketones such as methyl ethyl ketone and diethyl ketone; ethers such as diethyl ether, diisopropyl ether, tetrahydrofuran, dioxane, dimethoxyethane, diethylene glycol dimethyl ether; methanol, ethanol, n-propanol , Isopropanol n-butanol, isobutanol, t-butanol, isoamyl alcohol, diethylene glycol, glycerin, octanol, cyclohexanol, alcohols such as methyl cellosolve; nitriles such as acetonitrile and isobutyronitrile Amides such as formamide, N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, N-methylpyrrolidinone and hexamethylphosphorotriamide; sulfoxides such as dimethyl sulfoxide and sulfolane Water; or a mixture thereof, preferably amides, and more preferably N, N-dimethylformamide or N, N-dimethylacetamide.

  While the reaction temperature varies depending on the solvent, starting material, reagent and the like, it is generally 20 to 200 ° C., preferably 50 to 150 ° C.

  While the reaction time varies depending on the solvent, starting materials, reagents, reaction temperature, etc., it is generally 30 minutes to 48 hours, preferably 1 to 24 hours.

After completion of the reaction, the target compound of this step is isolated from the reaction mixture according to a conventional method. For example, water and a solvent immiscible with water (for example, benzene, diethyl ether, ethyl acetate, etc.) are added to the reaction mixture to extract the target compound, the organic layer is washed with water, and a drying agent such as anhydrous magnesium sulfate is used. After drying, the target compound is obtained by distilling off the solvent. The obtained target compound can be further purified by a conventional method such as recrystallization, reprecipitation, or silica gel column chromatography, if necessary.

(M method)
Method M is a method for producing compound (Iv) in which A ² is a 2-oxo-1,2-dihydropyridyl group or a 1,2-dihydro-2-thioxopyridyl group in formula (I). . Method M can also be applied to the production of compounds having formula (Ia). The M method can also be applied to the case where the same conversion is performed for A ¹ and A ³ .
(Step M-1)
In step M-1, compound (Iu) in which A ² is 2-methoxypyridyl group or 2-methylthiopyridyl group in formula (I) is treated with an acid, and in formula (I), A ² is , 2-oxo-1,2-dihydropyridyl group or 1,2-dihydro-2-thioxopyridyl group (Iv).

Compound (Iu) is obtained by using Method (A), Method B, Method E or Method F using Compound (6a) in which A ² is a 2-methoxypyridyl group or 2-methylthiopyridyl group in Compound (6) Alternatively, the compound (10) can be produced by the method C or D using the compound (10a) in which A ² is a 2-methoxypyridyl group or a 2-methylthiopyridyl group.

  Examples of the acid used include organic acids such as acetic acid, propionic acid, trifluoroacetic acid and pentafluoropropionic acid; organic sulfonic acids such as p-toluenesulfonic acid and trifluoromethanesulfonic acid; hydrochloric acid and hydrobromic acid Inorganic acids such as hydroiodic acid and phosphoric acid; hydrogen chloride solutions such as hydrogen chloride-dioxane solution and hydrogen chloride-methanol solution; trimethylsilyl iodide; boron-containing Lewis such as boron trifluoride and boron trichloride Acid; aluminum-containing Lewis acid such as aluminum chloride and aluminum bromide, preferably trifluoroacetic acid, hydrochloric acid, hydrogen chloride-dioxane solution, trimethylsilyl iodide or boron trifluoride, more preferably , Trifluoroacetic acid, hydrochloric acid or hydrogen chloride-dioxane solution.

  The solvent used is not particularly limited as long as it does not inhibit the reaction and dissolves the starting materials to some extent. For example, aliphatic hydrocarbons such as hexane and heptane; aromatics such as benzene, toluene and xylene Group hydrocarbons; halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, dichloroethane, chlorobenzene, dichlorobenzene; esters such as ethyl formate, ethyl acetate, propyl acetate, butyl acetate, diethyl carbonate; acetone Ketones such as methyl ethyl ketone and diethyl ketone; ethers such as diethyl ether, diisopropyl ether, tetrahydrofuran, dioxane, dimethoxyethane and diethylene glycol dimethyl ether; nitriles such as acetonitrile and isobutyronitrile; Amides such as amide, N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, N-methylpyrrolidinone and hexamethylphosphorotriamide; Sulfoxides such as dimethyl sulfoxide and sulfolane; Water; or mixtures thereof, preferably halogenated hydrocarbons, ethers, water, or mixtures thereof, more preferably methylene chloride, dioxane or dioxane-water mixtures. It is a solvent.

  While the reaction temperature varies depending on the solvent, starting material, reagent and the like, it is generally −20 to 150 ° C., preferably 0 to 100 ° C.

  While the reaction time varies depending on the solvent, starting materials, reagents, reaction temperature, etc., it is generally 30 minutes to 48 hours, preferably 1 to 24 hours.

After completion of the reaction, the target compound of this step is isolated from the reaction mixture according to a conventional method. For example, water and a solvent immiscible with water (for example, benzene, diethyl ether, ethyl acetate, etc.) are added to the reaction mixture to extract the target compound, the organic layer is washed with water, and a drying agent such as anhydrous magnesium sulfate is used. After drying, the target compound is obtained by distilling off the solvent. The obtained target compound can be further purified by a conventional method such as recrystallization, reprecipitation, or silica gel column chromatography, if necessary. In addition, the target compound of this step can be used in the next reaction without purification.

(N method)
Method N is a method for producing compound (Iw) in which R ¹ is a group having the formula —CO— in formula (I). Method N can also be applied to the production of compounds having formula (Ia).
(N-1 process)
In the N-1 step, the compound (10) obtained in the N-1 step is reacted with a known or easily obtained compound (24) from a known compound, and in the formula (I), R ¹ is This is a step for producing a compound (Iw) which is a group having the formula —CO—.

N-1 process is performed according to the method similar to B-2a process.

When the compound having the general formula (I) or the general formula (Ia) of the present invention or a pharmacologically acceptable salt thereof is used as a medicine, it may be used in combination with other medicines depending on the purpose. it can. There are no particular limitations on such combined drugs as long as they meet the purpose and exhibit the desired effects, and preferably insulin, sulfonylurea, α-glycosidase inhibitor, α-amylase inhibitor , Biguanide, PPAR-γ agonist, PPAR-γ antagonist, PPAR-α agonist, SGLT inhibitor, GLP-1 receptor antagonist, DPP-IV inhibitor, aldose reductase inhibitor, diabetic neuropathy, HMG -CoA reductase inhibitor, ACAT inhibitor, cholesterol absorption inhibitor, bile acid adsorbent, nicotinic acid, CETP inhibitor, antioxidant, calcium antagonist, angiotensin converting enzyme inhibitor, angiotensin II receptor antagonist, beta- 1 block selected from the group consisting of a blocker, an α1 blocker, an anti-obesity drug (therapeutic or preventive for obesity or obesity), and a low-energy diet Can be up to two drugs, preferably sulfonylurea, PPAR-γ agonist, biguanide, HMG-CoA reductase inhibitor, ACAT inhibitor, cholesterol absorption inhibitor, angiotensin II receptor antagonist, anti-obesity One or two drugs selected from the group consisting of a drug (obesity or obesity treatment or prevention drug) and a low-energy diet. The compound having the general formula (I) or the general formula (Ia) of the present invention or a pharmacologically acceptable salt thereof, and a concomitant drug of the above drugs are obesity, obesity, hyperlipidemia, hyperTGemia, Lipid metabolism disorders, insulin resistance syndrome, impaired glucose tolerance, diabetes, diabetic complications (including diabetic peripheral neuropathy, diabetic nephropathy, diabetic retinopathy, diabetic macroangiopathy, etc.), cataract, gestational diabetes , Polycystic ovary syndrome, arteriosclerosis (including arteriosclerosis caused by the diseases shown above and below), atherosclerosis, diabetic arteriosclerosis, or hyperlipidemia caused by obesity, high TGemia, dyslipidemia, insulin resistance syndrome, impaired glucose tolerance, diabetes, diabetic complications (including diabetic peripheral neuropathy, diabetic nephropathy, diabetic retinopathy, diabetic macroangiopathy), Cataract, gestational diabetes, polycyst Ovarian syndrome, arteriosclerosis (including arteriosclerosis caused by the diseases shown above and below), atherosclerosis, diabetic arteriosclerosis, hypertension, cerebrovascular disorder, coronary artery disease, fatty liver, breathing It is useful as a therapeutic or prophylactic agent for abnormalities, low back pain, knee osteoarthritis, gout, or cholelithiasis.

  When the compound having the general formula (I) or general formula (Ia) of the present invention or a pharmacologically acceptable salt thereof is used as a therapeutic or prophylactic agent for diseases, the general formula (I) or the general formula ( The compound having Ia) or a pharmacologically acceptable salt thereof can be administered by itself, or mixed with an appropriate pharmacologically acceptable excipient, diluent, etc., and tablet, capsule It can be administered orally in dosage forms such as pills, granules, powders or syrups, or parenterally in dosage forms such as injections, suppositories, patches or external preparations.

  These preparations are produced by known methods using additives such as excipients, lubricants, binders, disintegrants, emulsifiers, stabilizers, flavoring agents, and diluents.

  The excipient can be, for example, an organic excipient or an inorganic excipient. Organic excipients include, for example, sugar derivatives such as lactose, sucrose, sucrose, mannitol and sorbitol; starch derivatives such as corn starch, potato starch, pregelatinized starch and dextrin; cellulose derivatives such as crystalline cellulose; It can be rubber; dextran; or pullulan. Inorganic excipients include, for example, light anhydrous silicic acid, synthetic aluminum silicate, calcium silicate, magnesium silicate derivatives such as magnesium aluminate; phosphates such as calcium hydrogen phosphate; carbonates such as calcium carbonate; or Or a sulfate such as calcium sulfate.

  Lubricants include, for example, stearic acid; metal stearates such as calcium stearate and magnesium stearate; talc; colloidal silica; waxes such as beeswax and gay wax; boric acid; adipic acid; Sulfate; glycol; fumaric acid; sodium benzoate; DL-leucine; lauryl sulfate such as sodium lauryl sulfate and magnesium lauryl sulfate; silicic acid such as anhydrous silicic acid and silicic acid hydrate; or the above starch derivative obtain.

  The binder can be, for example, hydroxypropylcellulose, hydroxypropylmethylcellulose, polyvinylpyrrolidone, polyethylene glycol, or a derivative described in the above excipients.

  Disintegrants include, for example, low-substituted hydroxypropyl cellulose, carboxymethyl cellulose, carboxymethyl cellulose calcium, cellulose derivatives such as internally crosslinked sodium carboxymethyl cellulose; chemically modified starch / cellulose derivatives such as carboxymethyl starch and sodium carboxymethyl starch Or it may be cross-linked polyvinyl pyrrolidone.

  Emulsifiers include, for example, colloidal clays such as bentonite and bee gum; metal hydroxides such as magnesium hydroxide and aluminum hydroxide; anionic surfactants such as sodium lauryl sulfate and calcium stearate; benzalkonium chloride Or a nonionic surfactant such as polyoxyethylene alkyl ether, polyoxyethylene sorbitan fatty acid ester, sucrose fatty acid ester.

  Stabilizers include, for example, parahydroxybenzoates such as methylparaben and propylparaben; alcohols such as chlorobutanol, benzyl alcohol and phenylethyl alcohol; benzalkonium chloride; phenols such as phenol and cresol; thimerosal Dehydroacetic acid; or sorbic acid.

  The corrigent can be, for example, commonly used sweeteners, acidulants, fragrances and the like.

The compound having the general formula (I) or the general formula (Ia) of the present invention or a pharmacologically acceptable salt thereof can be administered as a medicine to a warm-blooded animal (particularly, human). The dose of the compound having the general formula (I) or the general formula (Ia) or a pharmacologically acceptable salt thereof varies depending on the disease, the age of the patient, and the like. Preferably, 5 mg), upper limit 1000 mg (preferably 500 mg), and in the case of intravenous administration, the lower limit is 0.1 mg (preferably 0.5 mg) and the upper limit is 500 mg (preferably, 250 mg) is preferably administered to adults 1 to 6 times per day, depending on the disease and its symptoms.

The compound having the general formula (I) or the general formula (Ia) of the present invention or a pharmacologically acceptable salt thereof has an excellent DGAT inhibitory action, and is used for warm-blooded animals (particularly humans). Disease, hyperlipidemia, hyperTGemia, dyslipidemia, insulin resistance syndrome, impaired glucose tolerance, diabetes, diabetic complications (diabetic peripheral neuropathy, diabetic nephropathy, diabetic retinopathy, diabetic Macrovascular disease etc.), cataract, gestational diabetes, polycystic ovary syndrome, arteriosclerosis (including arteriosclerosis caused by the diseases shown above and below), atherosclerosis, diabetic arteriosclerosis, Or obesity-related hyperlipidemia, hyperTG, dyslipidemia, insulin resistance syndrome, impaired glucose tolerance, diabetes, diabetic complications (diabetic peripheral neuropathy, diabetic nephropathy, diabetic retina , Including diabetic macroangiopathy , Cataract, gestational diabetes, polycystic ovary syndrome, arteriosclerosis (including arteriosclerosis due to the diseases shown above and below), atherosclerosis, diabetic arteriosclerosis, hypertension, cerebrovascular disorder, Coronary artery disease, fatty liver, respiratory abnormalities, low back pain, knee osteoarthritis, gout, or cholelithiasis, preferably obesity, obesity, hyperlipidemia, hyperTGemia, dyslipidemia, diabetes, Arteriosclerosis or hyperlipidemia due to obesity, hyperTGemia, dyslipidemia, diabetes, arteriosclerosis or hypertension, more preferably obesity, obesity, hyperlipidemia It is useful as a therapeutic agent or prophylactic agent (especially a therapeutic agent) for hyperTGemia, diabetes, or arteriosclerosis.

  EXAMPLES Hereinafter, although an Example, a test example, and a reference example are given and this invention is demonstrated further in detail, the scope of the present invention is not limited to these.

In the following examples, nuclear magnetic resonance (hereinafter, ¹ H-NMR) spectra were measured using a JNM-GX 270 FT-NMR measuring apparatus (JEOL). Using tetramethylsilane as a standard substance, the chemical shift value is described in δ value (ppm). The splitting pattern is indicated by s for single lines, d for double lines, t for triple lines, q for quadruple lines, and sep for seven lines.

  High performance liquid chromatography (hereinafter referred to as HPLC) -mass spectrometry was performed using HP-1100 LC / MSD (Heuret Packard). The measurement conditions of high performance liquid chromatography (hereinafter referred to as HPLC) are as follows. R.t. represents a retention time.

Column: CD-C18 (intact)
Moving bed: acetonitrile / water [with 0.01% trifluoroacetic acid and 0.5% acetic acid (v / v)] = 8 / 92-99 / 1 (v / v) (linear gradient for 10 minutes)
Flow rate: 1.5ml / min
Column temperature: 40 ° C
Detection wavelength: 254nm
Mass spectrometry (hereinafter referred to as MS) was performed by an atmospheric pressure chemical ionization method (hereinafter referred to as APCI).

(Example 1)
2- [N-Benzenesulfonyl-N- (3-trifluoromethylphenyl) amino] -N- (4-ethoxyphenyl) acetamide (compound of Exemplified Compound No. 1-117)
Using the benzenesulfonyl chloride for the building block -C (various sulfonyl chlorides) of Example 3, the reaction was carried out in the same manner as in Example 3 to obtain the title compound.
¹ H-NMR (DMSO-d ₆ ) δ: 9.95 (s, 1H), 7.76-7.47 (m, 9H), 7.37 (d, 2H, J = 8.9Hz), 6.84 (d, 2H, J = 8.9Hz ), 4.52 (s, 2H), 3.96 (q, 2H, J = 6.8Hz), 1.29 (t, 3H, J = 6.8Hz).
MS (APCI, m / z): 479 (M + H) ⁺ .
HPLC; Rt = 5.47min.

(Example 2)
2- [N-Benzenesulfonyl-N- (4-ethoxyphenyl) amino] -N- (4-ethoxyphenyl) acetamide (compound of Exemplified Compound No. 1-189)
This group of compounds was synthesized by using the encoding synthesis method by IRORI's MiniKans (registered trademark).

  Ten MiniKan identified by RF tag (radio frequency tag) were each 2- (3,5-dimethoxy-4-formylphenoxy) ethoxymethyl polystyrene resin (Novabiochem, 0.78 mmol / g; 100 mg x 10, All microreactors encapsulating 0.78 mmol) were combined and swollen in N, N-dimethylacetamide-acetic acid (9: 1, 70 ml). Magnesium sulfate (228 mg, 1.89 mmol) and p-phenetidine (2.22 ml, 17.2 mmol) were added to the container, and the mixture was heated and stirred at 80 ° C. for 1 hour in a nitrogen atmosphere. Thereafter, sodium triacetoxyborohydride (3.65 g, 17.2 mmol) was added to the reaction system, and the mixture was heated and stirred at 80 ° C. for 22 hours. The reaction system was cooled to room temperature, and the resin was washed several times with warm water, N, N-dimethylformamide, tetrahydrofuran, methanol, and dichloromethane, washed with diethyl ether, and dried under reduced pressure.

  Next, 9 microreactors (0.78 mmol / g; 100 mg × 9, 0.702 mmol) were swollen in N, N-dimethylacetamide (50 ml) and cooled to 0 ° C. in a nitrogen atmosphere. Thereafter, bromoacetyl bromide (0.61 ml, 7.02 mmol) was added over 3 minutes, and the mixture was stirred for 19 hours while slowly warming from 0 ° C. to room temperature. Thereafter, the resin was washed several times with N, N-dimethylformamide, tetrahydrofuran, methanol and dichloromethane, then with diethyl ether and dried under reduced pressure.

  Subsequently, the microreactor (0.78 mmol / g; 100 mg × 1 piece, 0.078 mmol) was swollen in dimethyl sulfoxide (4.0 ml), p-phenetidine (0.20 ml, 1.56 mmol) was added, and the mixture was placed under a nitrogen atmosphere. The mixture was heated and stirred at 80 ° C. for 21 hours. The reaction system was cooled to room temperature, and the resin was washed several times with N, N-dimethylformamide, tetrahydrofuran, methanol, and dichloromethane, then washed with diethyl ether, and dried under reduced pressure.

  Subsequently, the microreactor (0.78 mmol / g; 100 mg x 1 piece, 0.078 mmol) was swollen in pyridine (4.0 ml), and benzenesulfonyl chloride (0.10 ml, 0.78 mmol) and 4- (dimethylamino) pyridine (Catalyst amount, about 2 mg) was added, and the mixture was stirred with heating at 70 ° C. for 19 hours under a nitrogen atmosphere. The reaction system was cooled to room temperature, and the resin was washed several times with tetrahydrofuran, methanol, and dichloromethane, then with diethyl ether, and dried under reduced pressure.

This microreactor was treated with 25% trifluoroacetic acid in dichloromethane for 20 hours. After concentration, the residue was dissolved by adding ethyl acetate, the solution was simply purified by silica gel filtration, concentrated, and then n-hexane. -The title compound (16 mg, 45%) was obtained by washing with a mixed solvent of ethyl acetate.
MS (APCI, m / z): 455 (M + H) ⁺ .
HPLC; Rt = 5.40min.

(Example 3)
2- [N- (4-tert-butylbenzenesulfonyl) -N- (3-trifluoromethylphenyl) amino] -N- (4-ethoxyphenyl) acetamide (compound of Exemplified Compound No. 1-124)
This group of compounds was synthesized by using the encoding synthesis method by IRORI's MiniKans (registered trademark).

  96 MiniKans identified by RF tag were each 2- (3,5-dimethoxy-4-formylphenoxy) ethoxymethyl polystyrene resin (Novabiochem, 0.90 mmol / g; 104 mg × 96 = 9.98 g, 8.99 All of the microreactors encapsulating mmol) were combined and swollen in N, N-dimethylacetamide-acetic acid (9: 1, 300 ml). Magnesium sulfate (1.19 g, 9.88 mmol) and p-phenetidine (11.6 ml, 89.9 mmol) were added, and the mixture was stirred with heating at 80 ° C. for 1 hour under a nitrogen atmosphere. Thereafter, sodium triacetoxyborohydride (19.0 g, 89.9 mmol) was added to the reaction system, and the mixture was heated and stirred at 80 ° C. for 22 hours. The reaction system was cooled to room temperature, and the resin was washed several times with warm water, N, N-dimethylformamide, tetrahydrofuran, methanol, and dichloromethane, washed with diethyl ether, and dried under reduced pressure.

  Next, all microreactors (0.90 mmol / g; 104 mg × 96, 8.99 mmol) were swollen in N, N-dimethylacetamide (500 ml), cooled to 0 ° C. in a nitrogen atmosphere, Bromoacetyl chloride (7.83 ml, 89.9 mmol) was added over 3 minutes, and the mixture was stirred for 18 hours while slowly warming from 0 ° C. to room temperature. Thereafter, the resin was washed several times with N, N-dimethylformamide, tetrahydrofuran, methanol, and dichloromethane, and then washed with diethyl ether and dried under reduced pressure.

  Subsequently, all microreactors (0.90 mmol / g; 104 mg × 96, 8.99 mmol) were swollen in dimethyl sulfoxide (300 ml), and 3-trifluoromethylaniline (16.7 ml, 13.5 mmol) was added. The mixture was heated and stirred at 80 ° C. for 22 hours under a nitrogen atmosphere. The reaction system was cooled to room temperature, and the resin was washed several times with N, N-dimethylformamide, tetrahydrofuran, methanol and dichloromethane, then with diethyl ether and dried under reduced pressure.

  Subsequently, after dividing the microreactors into 96 types according to the instructions of the RF tag, the microreactors (0.90 mmol / g; 104 mg × 1 piece, 0.094 mmol) were swollen in pyridine (4.0 ml), and the building block − C (various sulfonyl chlorides) [eg 4-tert-butylbenzenesulfonyl chloride (232 mg, 1.0 mmol)] and 4- (dimethylamino) pyridine (catalytic amount, about 2 mg) are added and the mixture is placed under a nitrogen atmosphere. The mixture was heated and stirred at 70 ° C. for 19 hours. The reaction system was cooled to room temperature, and all the microreactors that reacted separately were combined. The resin was washed several times with tetrahydrofuran, methanol, and dichloromethane, then washed with diethyl ether, and dried under reduced pressure.

Subsequently, after dividing these microreactors into 96 types according to the instructions of the RF tag, each microreactor was treated with 25% trifluoroacetic acid in dichloromethane for 15 hours, concentrated and then subjected to appropriate purification operations to obtain the title compound. Obtained.
MS (APCI, m / z): 535 (M + H) ⁺ .
HPLC; Rt = 6.81min.

Example 4
N- (4-Ethoxyphenyl) -2- [N- (4-trifluoromethylbenzenesulfonyl) -N- (3-trifluoromethylphenyl) amino] acetamide (compound of Exemplified Compound No. 1-126)
The title compound was obtained in the same manner as in Example 3 except that 4-tert-butylbenzenesulfonyl chloride was used for building block-C (various sulfonyl chlorides) in Example 3. MS (APCI, m / z): 547 (M + H) ⁺ .
HPLC; Rt = 6.24min.

(Example 5)
2- [N- (5-Chlorothiophene-2-sulfonyl) -N- (3-trifluoromethylphenyl) amino] -N- (4-ethoxyphenyl) acetamide (compound of Exemplified Compound No. 1-162)
The title compound was obtained in the same manner as in Example 3 except that 5-chlorothiophene-2-sulfonyl chloride was used for building block-C (various sulfonyl chlorides) in Example 3. MS (APCI, m / z): 519 (M + H) ⁺ , 521 (M + H) ⁺ .
HPLC; Rt = 6.15min.

(Example 6)
N- (4-Ethoxyphenyl) -2- [N- (4-methoxybenzenesulfonyl) -N- (3-trifluoromethylphenyl) amino] acetamide (compound of Exemplified Compound No. 1-128)
The title compound was obtained in the same manner as in Example 3 except that 4-methoxybenzenesulfonyl chloride was used for building block -C (various sulfonyl chlorides) in Example 3.
MS (APCI, m / z): 509 (M + H) ⁺ .
HPLC; Rt = 5.66min.

(Example 7)
N- (4-Ethoxyphenyl) -2- [N- (thiophen-2-sulfonyl) -N- (3-trifluoromethylphenyl) amino] acetamide (compound of Exemplified Compound No. 1-160)
The title compound was obtained in the same manner as in Example 3 except that 2-thiophenesulfonyl chloride was used for building block -C (various sulfonyl chlorides) in Example 3.
MS (APCI, m / z): 485 (M + H) ⁺ .
HPLC; Rt = 5.48min.

(Example 8)
N- (4-Ethoxyphenyl) -2- [N- (4-trifluoromethoxybenzenesulfonyl) -N- (3-trifluoromethylphenyl) amino] acetamide (compound of Exemplified Compound No. 1-132)
The title compound was obtained in the same manner as in Example 3 except that 4- (trifluoromethoxy) benzenesulfonyl chloride was used for building block -C (various sulfonyl chlorides) in Example 3.
MS (APCI, m / z): 563 (M + H) ⁺ .
HPLC; Rt = 6.33min.

Example 9
N- (4-Ethoxyphenyl) -2- [N- (4-methanesulfonylbenzenesulfonyl) -N- (3-trifluoromethylphenyl) amino] acetamide (compound of Exemplified Compound No. 1-133)
The title compound was obtained in the same manner as in Example 3 except that 4-methanesulfonylbenzenesulfonyl chloride was used for building block-C (various sulfonyl chlorides) in Example 3.
MS (APCI, m / z): 557 (M + H) ⁺ .
HPLC; Rt = 5.15min.

(Example 10)
N- (4-Ethoxyphenyl) -2- [N- (toluene-4-sulfonyl) -N- (3-trifluoromethylphenyl) amino] acetamide (compound of Exemplified Compound No. 1-120)
Reaction was carried out in the same manner as in Example 3 using toluene-4-sulfonyl chloride for the building block -C (various sulfonyl chlorides) in Example 3 to obtain the title compound.
MS (APCI, m / z): 493 (M + H) +.
HPLC; Rt = 5.92min.

(Example 11)
N- (4-Ethoxyphenyl) -2- [N- (3-nitrobenzenesulfonyl) -N- (3-trifluoromethylphenyl) amino] acetamide (compound of Exemplified Compound No. 1-138)
The title compound was obtained in the same manner as in Example 3 except that 3-nitrobenzenesulfonyl chloride was used for building block-C (various sulfonyl chlorides) in Example 3.
MS (APCI, m / z): 524 (M + H) ⁺ .
HPLC; Rt = 5.70min.

(Example 12)
2- [N- (2-acetylamino-4-methylthiazole-5-sulfonyl) -N- (3-trifluoromethylphenyl) amino] -N- (4-ethoxyphenyl) acetamide (Exemplified Compound No. 1-165 Compound)
Using 2-acetamido-4-methyl-5-thiazolesulfonyl chloride for the building block -C (various sulfonyl chlorides) of Example 3, the reaction was carried out in the same manner as in Example 3 to obtain the title compound.
MS (APCI, m / z): 557 (M + H) ⁺ .
HPLC; Rt = 4.92min.

(Example 13)
2- [N- (4-acetylaminobenzenesulfonyl) -N- (3-trifluoromethylphenyl) amino] -N- (4-ethoxyphenyl) acetamide (compound of Exemplified Compound No. 1-134)
Using 4-acetylaminobenzenesulfonyl chloride as the building block -C (various sulfonyl chlorides) in Example 3, the reaction was carried out in the same manner as in Example 3 to obtain the title compound.
MS (APCI, m / z): 536 (M + H) ⁺ .
HPLC; Rt = 4.89min.

(Example 14)
2- [N- (4-Chlorobenzenesulfonyl) -N- (3-trifluoromethylphenyl) amino] -N- (4-ethoxyphenyl) acetamide (Compound No. 1-145)
Using 4-chlorobenzenesulfonyl chloride as the building block -C (various sulfonyl chlorides) of Example 3, the reaction was carried out in the same manner as in Example 3 to obtain the title compound.
MS (APCI, m / z): 513 (M + H) ⁺ , 515 (M + H) ⁺ .
HPLC; Rt = 6.12min.

(Example 15)
N- (4-Ethoxyphenyl) -2- [N- (3-methoxybenzenesulfonyl) -N- (3-trifluoromethylphenyl) amino] acetamide (compound of Exemplified Compound No. 1-127)
The reaction was conducted in the same manner as in Example 3 using 3-methoxybenzenesulfonyl chloride for the building block -C (various sulfonyl chlorides) in Example 3 to obtain the title compound.
MS (APCI, m / z): 509 (M + H) ⁺ .
HPLC; Rt = 5.73 min.

(Example 16)
2- [N- (6-Chloroimidazo [2,1-b] thiazole-5-sulfonyl) -N- (3-trifluoromethylphenyl) amino] -N- (4-ethoxyphenyl) acetamide (Exemplary Compound No. 1-181 compounds)
Using 6-chloroimidazo [2,1-b] thiazole-5-sulfonyl chloride as the building block -C (various sulfonyl chlorides) of Example 3, the reaction was carried out in the same manner as in Example 3 to obtain the title compound. .
MS (APCI, m / z): 559 (M + H) ⁺ , 561 (M + H) ⁺ .
HPLC; Rt = 5.50min.

(Example 17)
N- (4-Ethoxyphenyl) -2- [N- (4-fluorobenzenesulfonyl) -N- (3-trifluoromethylphenyl) amino] acetamide (compound of Exemplified Compound No. 1-142)
The title compound was obtained in the same manner as in Example 3 except that 4-fluorobenzenesulfonyl chloride was used for building block -C (various sulfonyl chlorides) in Example 3.
MS (APCI, m / z): 497 (M + H) ^<+> .
HPLC; Rt = 5.78min.

(Example 18)
N- (4-Ethoxyphenyl) -2- [N- (naphthalene-2-sulfonyl) -N- (3-trifluoromethylphenyl) amino] acetamide (Compound No. 1-150)
The title compound was obtained in the same manner as in Example 3 except that 2-naphthalenesulfonyl chloride was used for building block-C (various sulfonyl chlorides) in Example 3.
MS (APCI, m / z): 529 (M + H) ⁺ .
HPLC; Rt = 6.20min.

(Example 19)
2- [N- (2-cyanobenzenesulfonyl) -N- (3-trifluoromethylphenyl) amino] -N- (4-ethoxyphenyl) acetamide (compound of Exemplified Compound No. 1-135)
The title compound was obtained in the same manner as in Example 3 except that 2-cyanobenzenesulfonyl chloride was used for building block-C (various sulfonyl chlorides) in Example 3.
MS (APCI, m / z): 504 (M + H) ⁺ .
HPLC; Rt = 5.37min.

(Example 20)
N- (4-Ethoxyphenyl) -2- [N- (3-fluoro-benzenesulfonyl) -N- (3-trifluoromethylphenyl) amino] acetamide (compound of Exemplified Compound No. 1-141)
The title compound was obtained in the same manner as in Example 3 except that 3-fluorobenzenesulfonyl chloride was used for building block -C (various sulfonyl chlorides) in Example 3.
MS (APCI, m / z): 497 (M + H) ^<+> .
HPLC; Rt = 5.81min.

(Example 21)
2- [N- (3-Chlorobenzenesulfonyl) -N- (3-trifluoromethylphenyl) amino] -N- (4-ethoxyphenyl) acetamide (Compound No. 1-144)
The reaction was conducted in the same manner as in Example 3 using 3-chlorobenzenesulfonyl chloride for the building block -C (various sulfonyl chlorides) in Example 3 to obtain the title compound.
MS (APCI, m / z): 513 (M + H) ⁺ , 515 (M + H) ⁺ .
HPLC; Rt = 6.09 min.

(Example 22)
2- [N- (4-Butoxybenzenesulfonyl) -N- (3-trifluoromethylphenyl) amino] -N- (4-ethoxyphenyl) acetamide (compound of Exemplified Compound No. 1-131)
The title compound was obtained in the same manner as in Example 3 except that 4-butoxybenzenesulfonyl chloride was used for building block -C (various sulfonyl chlorides) in Example 3.
MS (APCI, m / z): 551 (M + H) ⁺ .
HPLC; Rt = 6.78min.

(Example 23)
2- [N- (Benzo [1,2,5] thiadiazole-4-sulfonyl) -N- (3-trifluoromethylphenyl) amino] -N- (4-ethoxyphenyl) acetamide (Exemplified Compound No. 1-182 Compound)
Using the benzo [1,2,5] thiadiazole-4-sulfonyl chloride for the building block -C (various sulfonyl chlorides) of Example 3, the reaction was carried out in the same manner as in Example 3 to obtain the title compound.
MS (APCI, m / z): 537 (M + H) ⁺ .
HPLC; Rt = 5.55min.

(Example 24)
2- [N- (biphenyl-4-sulfonyl) -N- (3-trifluoromethylphenyl) amino] -N- (4-ethoxyphenyl) acetamide (compound of Exemplified Compound No. 1-148)
The reaction was conducted in the same manner as in Example 3 using biphenyl-4-sulfonyl chloride as the building block -C (various sulfonyl chlorides) in Example 3 to obtain the title compound.
MS (APCI, m / z): 555 (M + H) ⁺ .
HPLC; Rt = 6.61min.

(Example 25)
2- [N- (1,2-dimethyl-1H-imidazole-4-sulfonyl) -N- (3-trifluoromethylphenyl) amino] -N- (4-ethoxyphenyl) acetamide (Exemplified Compound No. 1-157 Compound)
Using 1,2-dimethyl-1H-imidazole-4-sulfonyl chloride for the building block -C (various sulfonyl chlorides) of Example 3, the reaction was carried out in the same manner as in Example 3 to obtain the title compound.
MS (APCI, m / z): 497 (M + H) ^<+> .
HPLC; Rt = 4.72min.

(Example 26)
N- (4-Ethoxyphenyl) -2- [N- (4-nitrobenzenesulfonyl) -N- (3-trifluoromethylphenyl) amino] acetamide (compound of Exemplified Compound No. 1-139)
The title compound was obtained in the same manner as in Example 3 except that 4-nitrobenzenesulfonyl chloride was used for building block-C (various sulfonyl chlorides) in Example 3.
MS (APCI, m / z): 524 (M + H) ⁺ .
HPLC; Rt = 5.76min.

(Example 27)
2- [N- [4- (1-Butyl) benzenesulfonyl] -N- (3-trifluoromethylphenyl) amino] -N- (4-ethoxyphenyl) acetamide (compound of Exemplified Compound No. 1-123)
The title compound was obtained in the same manner as in Example 3 except that 4- (1-butyl) benzenesulfonyl chloride was used for building block-C (various sulfonyl chlorides) in Example 3.
MS (APCI, m / z): 535 (M + H) ⁺ .
HPLC; Rt = 6.97min.

(Example 28)
N- (4-Ethoxyphenyl) -2- [N- (toluene-2-sulfonyl) -N- (3-trifluoromethylphenyl) amino] acetamide (compound of Exemplified Compound No. 1-118)
The title compound was obtained in the same manner as in Example 3 except that toluene-2-sulfonyl chloride was used for building block-C (various sulfonyl chlorides) in Example 3.
MS (APCI, m / z): 493 (M + H) ⁺ .
HPLC; Rt = 5.92min.

(Example 29)
N- (4-Ethoxyphenyl) -2- [N- (3-trifluoromethylbenzenesulfonyl) -N- (3-trifluoromethylphenyl) amino] acetamide (compound of Exemplified Compound No. 1-125)
The title compound was obtained in the same manner as in Example 3 except that 3-trifluoromethylbenzenesulfonyl chloride was used for building block -C (various sulfonyl chlorides) in Example 3.
MS (APCI, m / z): 547 (M + H) ⁺ .
HPLC; Rt = 6.18min.


(Example 30)
N- (4-Ethoxyphenyl) -2- [N- (naphthalene-1-sulfonyl) -N- (3-trifluoromethylphenyl) amino] acetamide (compound of Exemplified Compound No. 1-149)
The title compound was obtained in the same manner as in Example 3 except that naphthalene-1-sulfonyl chloride was used for building block-C (various sulfonyl chlorides) in Example 3.
¹ H-NMR (DMSO-d ₆ ) δ: 9.93 (s, 1H), 8.30 (d, 1H, J = 8.4Hz), 8.20-8.13 (m, 2H), 8.11 (d, 1H, J = 7.8Hz ), 7.69-7.59 (m, 3H), 7.46 (s, 1H), 7.35 (d, 2H, J = 9.0Hz), 6.83 (d, 2H, J = 9.0Hz), 4.61 (s, 2H), 3.95 (q, 2H, J = 6.8Hz), 1.29 (t, 3H, J = 6.8Hz).
MS (APCI, m / z): 529 (M + H) ⁺ .
HPLC; Rt = 6.17min.

(Example 31)
N- (4-Ethoxyphenyl) -2- [N- (2-fluorobenzenesulfonyl) -N- (3-trifluoromethylphenyl) amino] acetamide (compound of Exemplified Compound No. 1-140)
The title compound was obtained in the same manner as in Example 3 except that 2-fluoro-benzenesulfonyl chloride was used for the building block -C (various sulfonyl chlorides) in Example 3. MS (APCI, m / z): 497 (M + H) ^<+> .
HPLC; Rt = 5.61min.

(Example 32)
2- [N- (5-chloro-3-methylbenzo [b] thiophene-2-sulfonyl) -N- (3-trifluoromethylphenyl) amino] -N- (4-ethoxyphenyl) acetamide (Exemplary Compound No. 1 -168 compounds)
Using 5-chloro-3-methyl-benzo [b] thiophene-2-sulfonyl chloride as the building block -C (various sulfonyl chlorides) in Example 3, the reaction was conducted in the same manner as in Example 3 to obtain the title compound. It was.
MS (APCI, m / z): 583 (M + H) ⁺ , 585 (M + H) ⁺ .
HPLC; Rt = 6.87min.

(Example 33)
2- [N- (3,5-dimethylisoxazole-4-sulfonyl) -N- (3-trifluoromethylphenyl) amino] -N- (4-ethoxyphenyl) acetamide (Exemplary Compound No. 1-159 Compound)
Using 3,5-dimethyl-isoxazole-4-sulfonyl chloride for the building block -C (various sulfonyl chlorides) in Example 3, the reaction was carried out in the same manner as in Example 3 to obtain the title compound.
MS (APCI, m / z): 498 (M + H) ⁺ .
HPLC; Rt = 5.67min.

(Example 34)
N- (4-Ethoxyphenyl) -2- [N- (toluene-3-sulfonyl) -N- (3-trifluoromethylphenyl) amino] acetamide (compound of Exemplified Compound No. 1-119)
The title compound was obtained in the same manner as in Example 3 except that toluene-3-sulfonyl chloride was used for building block-C (various sulfonyl chlorides) in Example 3.
MS (APCI, m / z): 493 (M + H) ⁺ .
HPLC; Rt = 5.94min.

(Example 35)
2- [N- (2-Chlorobenzenesulfonyl) -N- (3-trifluoromethylphenyl) amino] -N- (4-ethoxyphenyl) acetamide (Compound No. 1-143)
Using the 2-chlorobenzenesulfonyl chloride for the building block -C (various sulfonyl chlorides) of Example 3, the reaction was carried out in the same manner as in Example 3 to obtain the title compound.
MS (APCI, m / z): 513 (M + H) ⁺ , 515 (M + H) ⁺ .
HPLC; Rt = 5.55min.

(Example 36)
N- (4-Ethoxyphenyl) -2- [N- (naphthalene-1-sulfonyl) -N- [3- (oxazol-5-yl) phenyl] amino] acetamide (compound of exemplary compound number 1-396)
This group of compounds was synthesized by using the encoding synthesis method by IRORI's MiniKans (registered trademark). 96 MiniKans identified by RF tags were each 2- (3,5-dimethoxy-4-formylphenoxy) ethoxymethyl polystyrene resin (Novabiochem, 0.90 mmol / g; 104 mg × 96 = 9.98 g, 8.99 All of the microreactors encapsulating mmol) were combined and swollen in N, N-dimethylacetamide-acetic acid (9: 1, 300 ml). Magnesium sulfate (1.19 g, 9.88 mmol) and p-phenetidine (11.6 ml, 89.9 mmol) were added, and the mixture was stirred with heating at 80 ° C. for 1 hour under a nitrogen atmosphere. Thereafter, sodium triacetoxyborohydride (19.0 g, 89.9 mmol) was added to the reaction system, and the mixture was heated and stirred at 80 ° C. for 22 hours. The reaction system was cooled to room temperature, and the resin was washed several times with warm water, N, N-dimethylformamide, tetrahydrofuran, methanol, and dichloromethane, washed with diethyl ether, and dried under reduced pressure.

  Next, all microreactors (0.90 mmol / g; 104 mg × 96, 8.99 mmol) were swollen in N, N-dimethylacetamide (500 ml), cooled to 0 ° C. in a nitrogen atmosphere, Bromoacetyl chloride (7.83 ml, 89.9 mmol) was added over 3 minutes, and the mixture was stirred for 18 hours while slowly warming from 0 ° C. to room temperature. Thereafter, the resin was washed several times with N, N-dimethylformamide, tetrahydrofuran, methanol, and dichloromethane, and then washed with diethyl ether and dried under reduced pressure.

  Subsequently, after dividing the microreactors into 96 types according to the instructions of the RF tag, the microreactors (0.90 mmol / g; 104 mg x 1 piece, 0.094 mmol) were swollen in dimethyl sulfoxide (4.0 ml), and the building block -B (various amines) [eg, 3- (1,3-oxazol-5-yl) aniline (216 mg, 1.35 mmol)] was added, and the mixture was heated and stirred at 80 ° C. for 20 hours under a nitrogen atmosphere. The reaction system was cooled to room temperature, and all the microreactors that had reacted separately were combined.The resin was washed several times with N, N-dimethylformamide, tetrahydrofuran, methanol, and dichloromethane, and then with diethyl ether. Dried under reduced pressure.

  Subsequently, 60 microreactors (0.90 mmol / g; 104 mg x 60, 56.2 mmol) with various building blocks-B suspended were swollen in pyridine (200 ml), and 1-naphthalenesulfonyl chloride (13.6 g , 60.0 mmol) and 4- (dimethylamino) pyridine (catalytic amount, about 120 mg) were added, and the mixture was heated and stirred at 70 ° C. for 20 hours under a nitrogen atmosphere. The reaction system was cooled to room temperature, and the resin was washed several times with tetrahydrofuran, methanol and dichloromethane, then with diethyl ether and dried under reduced pressure.

Subsequently, after dividing these microreactors into 60 types according to the instructions of the RF tag, each microreactor was treated with 25% trifluoroacetic acid in dichloromethane for 7 hours, concentrated, and then subjected to appropriate purification operations to obtain the title compound. Obtained.
MS (APCI, m / z): 528 (M + H) ⁺ .
HPLC; Rt = 5.17 min.

(Example 37)
N- (4-Ethoxyphenyl) -2- [N- (3-fluorophenyl) -N- (naphthalene-1-sulfonyl) amino] acetamide (compound of Exemplified Compound No. 1-221)
Using 3-fluoroaniline as the building block -B (various amines) of Example 36, the reaction was carried out in the same manner as in Example 36 to obtain the title compound.
MS (APCI, m / z): 479 (M + H) ⁺ .
HPLC; Rt = 5.70min.

(Example 38)
N- (4-Ethoxyphenyl) -2- [N- (4-fluorophenyl) -N- (naphthalene-1-sulfonyl) amino] acetamide (compound of Exemplified Compound No. 1-222)
Using 4-fluoroaniline as the building block -B (various amines) of Example 36, the reaction was carried out in the same manner as in Example 36 to obtain the title compound.
MS (APCI, m / z): 479 (M + H) ⁺ .
HPLC; Rt = 5.69min.

(Example 39)
N- (4-Ethoxy-phenyl) -2- [N- (4-fluoro-3-trifluoromethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetamide (compound of Exemplified Compound No. 1-374)
The title compound was obtained in the same manner as in Example 36 except that 4-fluoro-3-trifluoromethylaniline was used for building block-B (various amines) in Example 36.
MS (APCI, m / z): 547 (M + H) ⁺ .
HPLC; Rt = 6.20min.

(Example 40)
2- [N- (Benzo [1,3] dioxol-5-yl) -N- (naphthalene-1-sulfonyl) amino] -N- (4-ethoxyphenyl) acetamide (compound of Exemplified Compound No. 1-229)
Using 3,4-methylenedioxyaniline for building block-B (various amines) of Example 36, the reaction was carried out in the same manner as in Example 36 to obtain the title compound.
MS (APCI, m / z): 505 (M + H) ⁺ .
HPLC; Rt = 5.46min.

(Example 41)
N- (4-Ethoxyphenyl) -2- [N- (naphthalene-1-sulfonyl) -N- (p-tolyl) amino] acetamide (compound of Exemplified Compound No. 1-114)
Using p-toluidine for building block-B (various amines) of Example 36, the reaction was carried out in the same manner as in Example 36 to obtain the title compound.
MS (APCI, m / z): 475 (M + H) ⁺ .
HPLC; Rt = 5.92min.

(Example 42)
N- (4-Ethoxyphenyl) -2- [N- (naphthalene-1-sulfonyl) -N- (o-tolyl) amino] acetamide (compound of Exemplified Compound No. 1-110)
The reaction was conducted in the same manner as in Example 36 using o-toluidine as the building block -B (various amines) in Example 36 to obtain the title compound.
MS (APCI, m / z): 475 (M + H) ⁺ .
HPLC; Rt = 5.92min.

(Example 43)
2- [N- (3-cyanophenyl) -N- (naphthalene-1-sulfonyl) amino] -N- (4-ethoxyphenyl) acetamide (compound of Exemplified Compound No. 1-216)
The title compound was obtained in the same manner as in Example 36 except that 3-aminobenzonitrile was used for building block-B (various amines) in Example 36.
MS (APCI, m / z): 486 (M + H) ⁺ .
HPLC; Rt = 5.41min.

(Example 44)
N- (4-Ethoxyphenyl) -2- [N- (2-methoxyphenyl) -N- (naphthalene-1-sulfonyl) amino] acetamide (Compound of Exemplified Compound No. 1-185)
Using o-anisidine for building block-B (various amines) of Example 36, the reaction was carried out in the same manner as in Example 36 to obtain the title compound.
MS (APCI, m / z): 491 (M + H) ⁺ .
HPLC; Rt = 5.72min.

(Example 45)
N- (4-Ethoxyphenyl) -2- [N- (3-methoxyphenyl) -N- (naphthalene-1-sulfonyl) amino] acetamide (compound of Exemplified Compound No. 1-187)
The reaction was conducted in the same manner as in Example 36 using m-anisidine as the building block -B (various amines) in Example 36 to obtain the title compound.
MS (APCI, m / z): 491 (M + H) ⁺ .
HPLC; Rt = 5.59min.

(Example 46)
N- (4-Ethoxy-phenyl) -2- [N- (4-methoxyphenyl) -N- (naphthalene-1-sulfonyl) amino] acetamide (Compound No. 1-188)
The reaction was conducted in the same manner as in Example 36 using p-anisidine as the building block -B (various amines) in Example 36 to obtain the title compound.
MS (APCI, m / z): 491 (M + H) ⁺ .
HPLC; Rt = 5.58min.

(Example 47)
3- [N-[(4-Ethoxyphenylcarbamoyl) methyl] -N- (naphthalene-1-sulfonyl) amino] benzoic acid ethyl ester (compound of Exemplified Compound No. 1-211)
The title compound was obtained in the same manner as in Example 36 except that 3-aminobenzoic acid ethyl ester was used for building block-B (various amines) in Example 36.
MS (APCI, m / z): 533 (M + H) ⁺ .
HPLC; Rt = 5.84min.

(Example 48)
4- [N-[(4-Ethoxyphenylcarbamoyl) methyl] -N- (naphthalene-1-sulfonyl) amino] benzoic acid ethyl ester (compound of Exemplified Compound No. 1-212)
The title compound was obtained in the same manner as in Example 36 except that 4-aminobenzoic acid ethyl ester was used for building block-B (various amines) in Example 36.
MS (APCI, m / z): 533 (M + H) ⁺ .
HPLC; Rt = 5.88min.

(Example 49)
2- [N- (2-Phenylphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- (4-ethoxyphenyl) acetamide (compound of Exemplified Compound No. 1-386)
Using 2-aminobiphenyl as the building block -B (various amines) of Example 36, the reaction was carried out in the same manner as in Example 36 to obtain the title compound.
MS (APCI, m / z): 537 (M + H) ⁺ .
HPLC; Rt = 6.59min.

(Example 50)
2- [N- (3-phenylphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- (4-ethoxyphenyl) acetamide (compound of exemplary compound number 1-387)
The title compound was obtained by reacting in the same manner as in Example 36 using 3-aminobiphenyl as the building block -B (various amines) in Example 36.
MS (APCI, m / z): 537 (M + H) ⁺ .
HPLC; Rt = 6.46min.

(Example 51)
2- [N- (2,3-Dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- (4-ethoxyphenyl) acetamide (compound of Exemplified Compound No. 1-304)
Using 2,3-dimethylaniline for building block-B (various amines) of Example 36, the reaction was carried out in the same manner as in Example 36 to obtain the title compound.
¹ H-NMR (DMSO-d ₆ ) δ: 9.76 (s, 1H), 8.30 (d, 1H, J = 7.8Hz), 8.27 (d, 1H, J = 7.0Hz), 8.12-8.05 (m, 2H ), 7.64 (d, 1H, J = 7.6Hz), 7.61 (d, 1H, J = 7.8Hz), 7.49 (dd like, 1H, J = 7.3, 7.0Hz), 7.33 (d, 2H, J = 9.0 Hz), 7.49 (dd, 1H, J = 5.7, 2.7Hz), 6.95-6.87 (m, 2H), 6.81 (d, 2H, J = 9.0Hz), 4.51 (d, 1H, J = 16.5Hz), 4.29 (d, 1H, J = 16.5Hz), 3.95 (q, 2H, J = 6.9Hz), 2.13 (s, 3H), 1.85 (s, 3H), 1.28 (t, 3H, J = 6.9Hz).
MS (APCI, m / z): 487 (MH) ⁺ .
HPLC; Rt = 6.16min.

(Example 52)
2- [N- (2,6-dimethoxyphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- (4-ethoxyphenyl) acetamide (compound of exemplary compound number 1-378)
Reaction was carried out in the same manner as in Example 36 using 2,6-dimethoxyaniline for the building block -B (various amines) in Example 36 to obtain the title compound.
MS (APCI, m / z): 521 (M + H) ⁺ .
HPLC; Rt = 5.91 min.

(Example 53)
2- [N- (2,5-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- (4-ethoxyphenyl) acetamide (compound of Exemplified Compound No. 1-359)
Using 2,5-dimethylaniline as the building block -B (various amines) of Example 36, the reaction was carried out in the same manner as in Example 36 to obtain the title compound.
MS (APCI, m / z): 489 (M + H) ⁺ .
HPLC; Rt = 6.28min.

(Example 54)
2- [N- (2,4-Dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- (4-ethoxyphenyl) acetamide (Compound No. 1-357)
Using 2,4-dimethylaniline for building block-B (various amines) of Example 36, the reaction was carried out in the same manner as in Example 36 to obtain the title compound.
MS (APCI, m / z): 489 (M + H) ⁺ .
HPLC; Rt = 6.24min.

(Example 55)
2- [N- (3,4-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- (4-ethoxyphenyl) acetamide (compound of Exemplified Compound No. 1-363)
Reaction was carried out in the same manner as in Example 36 using 3,4-dimethylaniline as the building block -B (various amines) in Example 36 to obtain the title compound.
MS (APCI, m / z): 489 (M + H) ⁺ .
HPLC; Rt = 6.15min.

(Example 56)
2- [N- (3,5-Dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- (4-ethoxyphenyl) acetamide (Compound No. 1-365)
Reaction was carried out in the same manner as in Example 36 using 3,5-dimethylaniline for building block-B (various amines) in Example 36 to obtain the title compound.
MS (APCI, m / z): 489 (M + H) ⁺ .
HPLC; Rt = 6.26min.

(Example 57)
2- [N- (2,6-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- (4-ethoxyphenyl) acetamide (compound of exemplary compound number 1-361)
Reaction was carried out in the same manner as in Example 36 using 2,6-dimethylaniline for building block-B (various amines) in Example 36 to obtain the title compound.
MS (APCI, m / z): 489 (M + H) ⁺ .
HPLC; Rt = 6.30min.

(Example 58)
N- (4-Ethoxyphenyl) -2- [N- (naphthalene-1-sulfonyl) -N- (naphthalen-1-yl) amino] acetamide (compound of exemplary compound number 1-404)
Using 1-aminonaphthalene as the building block -B (various amines) of Example 36, the reaction was carried out in the same manner as in Example 36 to obtain the title compound.
MS (APCI, m / z): 511 (M + H) ⁺ .
HPLC; Rt = 6.06min.

(Example 59)
2- [N- (3,5-dimethoxyphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- (4-ethoxyphenyl) acetamide (compound of Exemplified Compound No. 1-381)
The title compound was obtained in the same manner as in Example 36 except that 3,5-dimethoxyaniline was used for building block-B (various amines) in Example 36.
MS (APCI, m / z): 521 (M + H) ⁺ .
HPLC; Rt = 5.60min.

(Example 60)
2- [N- (2,4-dimethoxyphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- (4-ethoxyphenyl) acetamide (compound of exemplary compound number 1-376)
The title compound was obtained in the same manner as in Example 36 except that 2,4-dimethoxyaniline was used for building block-B (various amines) in Example 36.
MS (APCI, m / z): 521 (M + H) ⁺ .
HPLC; Rt = 5.72min.

(Example 61)
2- [N- (3,4-dimethoxyphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- (4-ethoxyphenyl) acetamide (compound of Exemplified Compound No. 1-379)
Reaction was carried out in the same manner as in Example 36 using 3,4-dimethoxyaniline for building block-B (various amines) in Example 36 to obtain the title compound.
MS (APCI, m / z): 521 (M + H) ⁺ .
HPLC; Rt = 5.21min.

(Example 62)
N- (4-Ethoxyphenyl) -2- [N- (3-methoxy-5-trifluoromethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetamide (compound of Exemplified Compound No. 1-372)
The title compound was obtained in the same manner as in Example 36 except that 3-methoxy-5-trifluoromethylaniline was used for building block-B (various amines) in Example 36.
MS (APCI, m / z): 559 (M + H) ⁺ .
HPLC; Rt = 6.19min.

(Example 63)
N- (4-Ethoxyphenyl) -2- [N- (2-methoxy-5-trifluoromethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetamide (Compound No. 1-373)
Using 2-methoxy-5-trifluoromethylaniline for building block-B (various amines) of Example 36, the reaction was carried out in the same manner as in Example 36 to obtain the title compound.
MS (APCI, m / z): 559 (M + H) ⁺ .
HPLC; Rt = 6.15min.

(Example 64)
N- (4-Ethoxyphenyl) -2- [N- (4-methoxy-3-trifluoromethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetamide (compound of Exemplified Compound No. 1-371)
The title compound was obtained in the same manner as in Example 36 except that 4-methoxy-3-trifluoromethylaniline was used for building block-B (various amines) in Example 36.
MS (APCI, m / z): 559 (M + H) ⁺ .
HPLC; Rt = 5.94min.

(Example 65)
N- (4-Ethoxyphenyl) -2- [N- (naphthalene-1-sulfonyl) -N- (m-tolyl) amino] acetamide (compound of Exemplified Compound No. 1-112)
The reaction was conducted in the same manner as in Example 36 using m-toluidine as the building block -B (various amines) in Example 36 to obtain the title compound.
MS (APCI, m / z): 475 (M + H) ⁺ .
HPLC; Rt = 5.90min.

Example 66
N- (4-Ethoxyphenyl) -2- [N- (naphthalene-1-sulfonyl) -N-phenylamino] acetamide (compound of Exemplified Compound No. 1-109)
Reaction was carried out in the same manner as in Example 36 using aniline for the building block -B (various amines) in Example 36 to obtain the title compound.
MS (APCI, m / z): 461 (M + H) ⁺ .
HPLC; Rt = 5.65min.

(Example 67)
2- [N- (4-Chlorophenyl) -N- (naphthalene-1-sulfonyl) amino] -N- (4-ethoxyphenyl) acetamide (compound of Exemplified Compound No. 1-226)
The title compound was obtained in the same manner as in Example 36 except that 4-chloroaniline was used for building block-B (various amines) of Example 36.
MS (APCI, m / z): 495 (M + H) ⁺ , 497 (M + H) ⁺ .
HPLC; Rt = 6.07min.

Example 68
2- [N- (3-Chlorophenyl) -N- (naphthalene-1-sulfonyl) amino] -N- (4-ethoxyphenyl) acetamide (Compound No. 1-225)
The title compound was obtained by reacting in the same manner as in Example 36 using 3-chloroaniline as the building block -B (various amines) in Example 36.
MS (APCI, m / z): 495 (M + H) ⁺ , 497 (M + H) ⁺ .
HPLC; Rt = 5.99min.

(Example 69)
2- [N- (2,5-dimethoxyphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- (4-ethoxyphenyl) acetamide (compound of exemplary compound number 1-377)
The title compound was obtained in the same manner as in Example 36 except that 2,5-dimethoxyaniline was used for building block-B (various amines) in Example 36.
MS (APCI, m / z): 521 (M + H) ⁺ .
HPLC; Rt = 5.76min.

(Example 70)
N- (4-Ethoxyphenyl) -2- [N- (naphthalene-1-sulfonyl) -N- (4-trifluoromethylphenyl) amino] acetamide (compound of Exemplified Compound No. 1-183)
The title compound was obtained in the same manner as in Example 36 except that 4-trifluoromethylaniline was used for building block-B (various amines) in Example 36.
MS (APCI, m / z): 529 (M + H) ⁺ .
HPLC; Rt = 6.17min.

(Example 71)
N- (4-Ethoxyphenyl) -2- [N- (2-fluorophenyl) -N- (naphthalene-1-sulfonyl) amino] acetamide (compound of Exemplified Compound No. 1-220)
Using 2-fluoroaniline as the building block -B (various amines) of Example 36, the reaction was carried out in the same manner as in Example 36 to obtain the title compound.
MS (APCI, m / z): 479 (M + H) ⁺ .
HPLC; Rt = 5.66min.

(Example 72)
N- (4-Ethoxyphenyl) -2- [N- (naphthalene-1-sulfonyl) -N- (quinolin-6-yl) amino] acetamide (compound of exemplary compound number 1-526)
The title compound was obtained in the same manner as in Example 36 except that 6-aminoquinoline was used for building block-B (various amines) in Example 36.
MS (APCI, m / z): 512 (M + H) ⁺ .
HPLC; Rt = 4.61 min.

(Example 73)
2- [N- (3,4-Dihydro-2H-benzo [b] [1,4] dioxepin-7-yl) -N- (naphthalene-1-sulfonyl) amino] -N- (4-ethoxyphenyl) Acetamide (compound of Exemplified Compound No. 1-230)
The reaction was carried out in the same manner as in Example 36 except that 3,4-dihydro-2H-benzo [b] [1,4] dioxepin-7-amine was used for the building block-B (various amines) in Example 36. A compound was obtained.
MS (APCI, m / z): 533 (M + H) ⁺ .
HPLC; Rt = 5.61min.

(Example 74)
2- [N- (3-acetylphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- (4-ethoxyphenyl) acetamide (compound of Exemplified Compound No. 1-206)
The reaction was conducted in the same manner as in Example 36 using 3'-aminoacetophenone for building block -B (various amines) in Example 36 to obtain the title compound.
MS (APCI, m / z): 503 (M + H) ⁺ .
HPLC; Rt = 5.29min.

(Example 75)
N- (4-Ethoxyphenyl) -2- [N- (naphthalene-1-sulfonyl) -N- (3-nitrophenyl) amino] acetamide (compound of Exemplified Compound No. 1-218)
The title compound was obtained by reacting in the same manner as in Example 36 using 3-nitroaniline as the building block -B (various amines) in Example 36.
MS (APCI, m / z): 506 (M + H) ⁺ .
HPLC; Rt = 5.59min.

(Example 76)
2- [N- (2,3-Dimethoxyphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- (4-ethoxyphenyl) acetamide (compound of Exemplified Compound No. 1-375)
Using 2,3-dimethoxyaniline for building block-B (various amines) of Example 36, the reaction was carried out in the same manner as in Example 36 to obtain the title compound.
MS (APCI, m / z): 521 (M + H) ⁺ .
HPLC; Rt = 6.01 min.

(Example 77)
2- [N- (3,5-dichlorophenyl) -N- (naphthalene-1-sulfonyl) amino] -N- (4-ethoxyphenyl) acetamide (compound of Exemplified Compound No. 1-385)
Using 3,5-dichloroaniline for building block-B (various amines) of Example 36, the reaction was carried out in the same manner as in Example 36 to obtain the title compound.
MS (APCI, m / z): 529 (M + H) ⁺ , 531 (M + H) ⁺ .
HPLC; Rt = 6.59min.

(Example 78)
N- (4-Ethoxyphenyl) -2- [N- (4-methylnaphthalene-1-sulfonyl) -N- (3-trifluoromethylphenyl) amino] acetamide (compound of Exemplified Compound No. 1-151)
Using 4-methylnaphthalene-1-sulfonyl chloride for building block-C (various sulfonyl chlorides) of Example 3, the reaction was carried out in the same manner as in Example 3 to obtain the title compound.
MS (APCI, m / z): 543 (M + H) ⁺ .
HPLC; Rt = 6.36min.

(Example 79)
2- [N- (5-dimethylaminonaphthalene-1-sulfonyl) -N- (3-trifluoromethylphenyl) amino] -N- (4-ethoxyphenyl) acetamide (compound of exemplary compound number 1-154)
The building block -C (various sulfonyl chlorides) in Example 3 was reacted in the same manner as in Example 3 using 5-dimethylaminonaphthalene-1-sulfonyl chloride to obtain the title compound.
MS (APCI, m / z): 572 (M + H) ⁺ .
HPLC; Rt = 6.50min.

(Example 80)
2- [N- (3,4-dichlorophenyl) -N- (naphthalene-1-sulfonyl) amino] -N- (4-ethoxyphenyl) acetamide (compound of exemplary compound number 1-384)
Reaction was carried out in the same manner as in Example 36 using 3,4-dichloroaniline for building block-B (various amines) in Example 36 to obtain the title compound.
MS (APCI, m / z): 529 (M + H) ⁺ , 531 (M + H) ⁺ .
HPLC; Rt = 6.45min.

(Example 81)
2- [N- (4-acetylphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- (4-ethoxyphenyl) acetamide (compound of exemplary compound number 1-207)
Using 4'-aminoacetophenone for building block-B (various amines) of Example 36, the reaction was carried out in the same manner as in Example 36 to obtain the title compound.
MS (APCI, m / z): 503 (M + H) ⁺ .
HPLC; Rt = 5.26min.

(Example 82)
N- (4-Ethoxyphenyl) -2- [N- (naphthalene-1-sulfonyl) -N- (2-trifluoromethoxyphenyl) amino] acetamide (compound of Exemplified Compound No. 1-190)
The title compound was obtained in the same manner as in Example 36 except that 2-trifluoromethoxyaniline was used for building block-B (various amines) in Example 36.
MS (APCI, m / z): 545 (M + H) ⁺ .
HPLC; Rt = 6.17min.

(Example 83)
2- [N- (2-acetylphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- (4-ethoxyphenyl) acetamide (compound of exemplary compound number 1-205)
Using 2'-aminoacetophenone for building block -B (various amines) of Example 36, the reaction was carried out in the same manner as in Example 36 to obtain the title compound.
MS (APCI, m / z): 503 (M + H) ⁺ .
HPLC; Rt = 5.84min.

(Example 84)
2- [N-[(4-Ethoxyphenylcarbamoyl) methyl] -N- (naphthalene-1-sulfonyl) amino] benzoic acid ethyl ester (compound of Exemplified Compound No. 1-210)
The title compound was obtained in the same manner as in Example 36 except that 2-aminobenzoic acid ethyl ester was used for building block-B (various amines) in Example 36.
MS (APCI, m / z): 533 (M + H) ⁺ .
HPLC; Rt = 6.37min.

(Example 85)
2- [N- (2-Chlorophenyl) -N- (naphthalene-1-sulfonyl) amino] -N- (4-ethoxyphenyl) acetamide (Compound No. 1-223)
Using 2-chloroaniline as the building block -B (various amines) of Example 36, the reaction was carried out in the same manner as in Example 36 to obtain the title compound.
MS (APCI, m / z): 495 (M + H) ⁺ , 497 (M + H) ⁺ .
HPLC; Rt = 5.91 min.

(Example 86)
N- (4-Ethoxyphenyl) -2- [N- (6-methoxypyridin-3-yl) -N- (naphthalene-1-sulfonyl) amino] acetamide (compound of Exemplified Compound No. 1-474)
The title compound was obtained in the same manner as in Example 36 except that 5-amino-2-methoxypyridine was used for building block-B (various amines) in Example 36.
MS (APCI, m / z): 492 (M + H) ⁺ .
HPLC; Rt = 5.38min.

(Example 87)
2- [N- (2,6-dimethoxypyridin-3-yl) -N- (naphthalene-1-sulfonyl) amino] -N- (4-ethoxyphenyl) acetamide (compound of exemplary compound number 1-475)
The title compound was obtained in the same manner as in Example 36 except that 3-amino-2,6-dimethoxypyridine was used for building block-B (various amines) in Example 36.
MS (APCI, m / z): 522 (M + H) ⁺ .
HPLC; Rt = 5.99min.

(Example 88)
N- (4-Ethoxyphenyl) -2- [N- (5-methylthiazol-2-yl) -N- (naphthalene-1-sulfonyl) amino] acetamide (compound of exemplary compound number 1-425)
The title compound was obtained in the same manner as in Example 36 except that 2-amino-5-methylthiazole was used for building block-B (various amines) in Example 36.
MS (APCI, m / z): 482 (M + H) ⁺ .
HPLC; Rt = 4.82min.

Example 89
N- (4-Ethoxyphenyl) -2- [N- (2-ethyl-1-hexyl) -N- (naphthalene-1-sulfonyl) amino] acetamide (compound of exemplary compound number 1-79)
Using 2-ethyl-1-hexylamine for building block-B (various amines) of Example 36, the reaction was carried out in the same manner as in Example 36 to obtain the title compound.
MS (APCI, m / z): 497 (M + H) ^<+> .
HPLC; Rt = 6.87min.

(Example 90)
N- (4-Ethoxyphenyl) -2- [N- [2- (morpholin-4-yl) ethyl] -N- (naphthalene-1-sulfonyl) amino] acetamide (compound of exemplary compound number 1-99)
Reaction was carried out in the same manner as in Example 36 using N- (2-aminoethyl) morpholine as the building block -B (various amines) in Example 36 to obtain the title compound.
MS (APCI, m / z): 498 (M + H) ⁺ .
HPLC; Rt = 3.67min.

(Example 91)
4- [N-[(4-Ethoxyphenylcarbamoyl) methyl] -N- (naphthalene-1-sulfonyl) amino] piperidine-1-carboxylic acid ethyl ester (compound of exemplary compound number 1-477)
The title compound was obtained in the same manner as in Example 36 except that 4-amino-1-piperidine-1-carboxylic acid ethyl ester was used for building block-B (various amines) of Example 36.
MS (APCI, m / z): 540 (M + H) ⁺ .
HPLC; Rt = 5.21min.

(Example 92)
2- [N-cyclobutyl-N- (naphthalene-1-sulfonyl) amino] -N- (4-ethoxyphenyl) acetamide (compound of Exemplified Compound No. 1-103)
The title compound was obtained in the same manner as in Example 36 except that aminocyclobutane was used for building block-B (various amines) in Example 36.
MS (APCI, m / z): 439 (M + H) ⁺ .
HPLC; Rt = 5.47min.

(Example 93)
2- [N-cyclopentyl-N- (naphthalene-1-sulfonyl) amino] -N- (4-ethoxyphenyl) acetamide (compound of exemplary compound number 1-104)
The title compound was obtained in the same manner as in Example 36 except that cyclopentylamine was used for building block-B (various amines) of Example 36.
MS (APCI, m / z): 453 (M + H) ⁺ .
HPLC; Rt = 5.75min.

(Example 94)
2- [N-cyclopropyl-N- (naphthalene-1-sulfonyl) amino] -N- (4-ethoxyphenyl) acetamide (compound of Exemplified Compound No. 1-102)
Reaction was carried out in the same manner as in Example 36 using cyclopropylamine as the building block-B (various amines) in Example 36 to obtain the title compound.
MS (APCI, m / z): 425 (M + H) ⁺ .
HPLC; Rt = 5.15min.

(Example 95)
N- (4-Ethoxyphenyl) -2- [N- (indan-2-yl) -N- (naphthalene-1-sulfonyl) amino] acetamide (Compound of Exemplified Compound No. 1-407)
Using 2-aminoindane for building block-B (various amines) of Example 36, the reaction was carried out in the same manner as in Example 36 to obtain the title compound.
MS (APCI, m / z): 501 (M + H) ⁺ .
HPLC; Rt = 5.97min.

(Example 96)
N- (4-Ethoxyphenyl) -2- [N- (1-methyl-3-phenylpropyl) -N- (naphthalene-1-sulfonyl) amino] acetamide (compound of exemplary compound number 1-95)
The title compound was obtained in the same manner as in Example 36 except that 3-amino-1-phenylbutane was used for building block-B (various amines) in Example 36.
MS (APCI, m / z): 517 (M + H) ⁺ .
HPLC; Rt = 6.29min.

(Example 97)
N- (4-Ethoxyphenyl) -2- [N- [2- (4-methoxyphenyl) ethyl] -N- (naphthalene-1-sulfonyl) amino] acetamide (compound of exemplary compound number 1-93)
The title compound was obtained in the same manner as in Example 36 except that 2- (4-methoxyphenyl) ethylamine was used for building block-B (various amines) in Example 36.
MS (APCI, m / z): 519 (M + H) ⁺ .
HPLC; Rt = 5.75min.

(Example 98)
N- (4-Ethoxyphenyl) -2- [N- (3-methylsulfanyl-1-propyl) -N- (naphthalene-1-sulfonyl) amino] acetamide (compound of exemplary compound number 1-84)
The title compound was obtained in the same manner as in Example 36 except that 3-methylsulfanyl-1-propylamine was used for building block-B (various amines) in Example 36.
MS (APCI, m / z): 473 (M + H) ⁺ .
HPLC; Rt = 5.43min.

Example 99
N- (4-Ethoxyphenyl) -2- [N- (4-methylcyclohexyl) -N- (naphthalene-1-sulfonyl) amino] acetamide (compound of Exemplified Compound No. 1-107)
The title compound was obtained in the same manner as in Example 36 except that 4-methylcyclohexylamine was used for building block-B (various amines) in Example 36.
MS (APCI, m / z): 481 (M + H) ⁺ .
HPLC; Rt = 6.35min, 6.43min (diastereomer).

(Example 100)
N- (4-Ethoxyphenyl) -2- [N- (2-methoxypyridin-3-yl) -N- (naphthalene-1-sulfonyl) amino] acetamide (compound of exemplary compound number 1-442)
The title compound was obtained in the same manner as in Example 36 except that 3-amino-2-methoxypyridine was used for building block-B (various amines) in Example 36.
MS (APCI, m / z): 492 (M + H) ⁺ .
HPLC; Rt = 5.25min.

(Example 101)
N- (4-Ethoxyphenyl) -2- [N- (naphthalene-1-sulfonyl) -N- (quinolin-3-yl) amino] acetamide (compound of exemplary compound number 1-525)
The title compound was obtained in the same manner as in Example 36 except that 3-aminoquinoline was used for building block-B (various amines) in Example 36.
MS (APCI, m / z): 512 (M + H) ⁺ .
HPLC; Rt = 5.09min.

(Example 102)
N- (4-Ethoxyphenyl) -2- [N- [6- (morpholin-4-yl) pyridin-3-yl] -N- (naphthalene-1-sulfonyl) amino] acetamide (Exemplified Compound No. 1-522 Compound)
The title compound was obtained in the same manner as in Example 36 except that 3-amino-6- (morpholin-4-yl) pyridine was used for building block-B (various amines) of Example 36.
MS (APCI, m / z): 547 (M + H) ⁺ .
HPLC; Rt = 4.76min.

(Example 103)
N- (4-Ethoxyphenyl) -2- [N- (6-methoxybenzothiazol-2-yl) -N- (naphthalene-1-sulfonyl) amino] acetamide (compound of exemplary compound number 1-524)
The title compound was obtained in the same manner as in Example 36 except that 2-amino-6-methoxybenzothiazole was used for building block-B (various amines) in Example 36.
MS (APCI, m / z): 548 (M + H) ⁺ .
HPLC; Rt = 5.18min.

(Example 104)
N- (4-Ethoxyphenyl) -2- [N- (naphthalene-1-sulfonyl) -N- [2- (thiophen-2-yl) ethyl] amino] acetamide (compound of exemplary compound number 1-96)
The title compound was obtained in the same manner as in Example 36 except that 2- (thiophen-2-yl) ethylamine was used for building block-B (various amines) in Example 36.
MS (APCI, m / z): 495 (M + H) ⁺ .
HPLC; Rt = 5.76min.

(Example 105)
N- (4-methoxyphenyl) -N-methyl-2- [N- (naphthalene-1-sulfonyl) -N- (3-trifluoromethylphenyl) amino] acetamide (compound of Exemplified Compound No. 2-5)
Naphthalene-1-sulfonic acid [N- (3-trifluoromethylphenyl)] amide prepared in Reference Example 4 and 2-bromo- [N- (4-methoxyphenyl) -N— prepared in Reference Example 10 Methyl] acetamide was used in the same manner as in Example 181 to obtain the title compound.
MS (APCI, m / z): 529 (M + H) ⁺ .
HPLC; Rt = 5.80min.

(Example 106)
2- [N- (3-dimethylamino-2,2-dimethyl-1-propyl) -N- (naphthalene-1-sulfonyl) amino] -N- (4-ethoxyphenyl) acetamide (Exemplary Compound No. 1-83 Compound)
Using the N, N-dimethyl-2,2-dimethyl-1,3-propanediamine as the building block-B (various amines) of Example 36, the reaction was carried out in the same manner as in Example 36 to obtain the title compound. .
MS (APCI, m / z): 498 (M + H) ⁺ .
HPLC; Rt = 3.91 min.

(Example 107)
N- (4-Ethoxyphenyl) -2- [N- (naphthalene-1-sulfonyl) -N- (2-phenyl-1-propyl) amino] acetamide (compound of exemplary compound number 1-89)
The title compound was obtained in the same manner as in Example 36 except that 2-phenyl-1-propylamine was used for building block-B (various amines) in Example 36.
MS (APCI, m / z): 503 (M + H) ⁺ .
HPLC; Rt = 6.36min.

(Example 108)
N- (4-Ethoxyphenyl) -2- [N- (1-phenoxy-2-propyl) -N- (naphthalene-1-sulfonyl) amino] acetamide (compound of exemplary compound number 1-101)
Using 1-phenoxy-2-propylamine for building block-B (various amines) of Example 36, the reaction was carried out in the same manner as in Example 36 to obtain the title compound.
MS (APCI, m / z): 519 (M + H) ⁺ .
HPLC; Rt = 6.14min.

(Example 109)
2- [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- (3-trifluoromethylphenyl) acetamide (compound of Exemplified Compound No. 1-32)
This group of compounds was synthesized by using the encoding synthesis method by IRORI's MiniKans (registered trademark). Each of the 60 MiniKan identified by the RF tag was 2- (3,5-dimethoxy-4-formylphenoxy) ethoxymethyl polystyrene resin (Novabiochem, 0.90 mmol / g; 110 mg × 1, 0.099 mmol) The enclosed microreactor was swollen in N, N-dimethylacetamide-acetic acid (9: 1, 4.0 ml). Magnesium sulfate (catalytic amount, approx. 10 mg) and building block-A (various amines) [eg 3-trifluoromethylaniline (242 mg, 1.50 mmol)] are added and the mixture is kept at 80 ° C. for 1 hour under nitrogen atmosphere. Stir with heating. Thereafter, sodium triacetoxyborohydride (318 mg, 1.50 mmol) was added to the reaction system, and the mixture was heated and stirred at 80 ° C. for 20 hours. The reaction system was cooled to room temperature, and all the microreactors that had been reacted separately were combined. The resin was washed several times with warm water, N, N-dimethylformamide, tetrahydrofuran, methanol, and dichloromethane, and then washed with diethyl ether. And dried under reduced pressure.

  Next, all microreactors (0.90 mmol / g; 110 mg × 60, 5.94 mmol) were swollen in N, N-dimethylacetamide (300 ml), cooled to 0 ° C. in a nitrogen atmosphere, and then brominated. Bromoacetyl (5.23 ml, 60.0 mmol) was added over 3 minutes, and the mixture was stirred for 19 hours while slowly warming from 0 ° C. to room temperature. Thereafter, the resin was washed several times with N, N-dimethylformamide, tetrahydrofuran, methanol, and dichloromethane, and then washed with diethyl ether and dried under reduced pressure.

  Subsequently, all microreactors (0.90 mmol / g; 110 mg x 60, 5.94 mmol) were swollen in dimethyl sulfoxide (200 ml), 2,3-dimethylaniline (11 ml, 90 mmol) was added, and the mixture Was stirred for 19 hours at 80 ° C. in a nitrogen atmosphere. The reaction system was cooled to room temperature, and the resin was washed several times with N, N-dimethylformamide, tetrahydrofuran, methanol and dichloromethane, then with diethyl ether and dried under reduced pressure.

  Subsequently, all microreactors (0.90 mmol / g; 110 mg x 60, 5.94 mmol) were swollen in pyridine (200 ml), and 1-naphthalenesulfonyl chloride (13.6 g, 60.0 mmol) and 4- (dimethylamino) ) Pyridine (catalytic amount, about 120 mg) was added and the mixture was heated and stirred at 70 ° C. for 20 hours under a nitrogen atmosphere. The reaction system was cooled to room temperature, and the resin was washed several times with tetrahydrofuran, methanol and dichloromethane, then with diethyl ether and dried under reduced pressure.

After dividing these microreactors into 60 types according to the instructions of the RF tag, each microreactor was treated with 25% trifluoroacetic acid in dichloromethane for 9 hours, concentrated, and then appropriately purified to obtain the title compound. .
MS (APCI, m / z): 513 (M + H) ⁺ .
HPLC; Rt = 6.59min.

(Example 110)
2- [N- (2,3-Dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- (4-trifluoromethoxyphenyl) acetamide (compound of exemplary compound number 1-561)
The title compound was obtained in the same manner as in Example 109 except that 4- (trifluoromethoxy) aniline was used for building block-A (various amines) of Example 109.
MS (APCI, m / z): 529 (M + H) ⁺ .
HPLC; Rt = 6.67min.

(Example 111)
2- [N- (2,3-Dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- (4-trifluoromethylphenyl) acetamide (compound of Exemplified Compound No. 1-32)
Using 4-trifluoromethylaniline for building block-A (various amines) of Example 109, the reaction was carried out in the same manner as in Example 109 to obtain the title compound.
MS (APCI, m / z): 513 (M + H) ⁺ .
HPLC; Rt = 6.63min.

(Example 112)
2- [N- (2,3-Dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- (4-fluorophenyl) acetamide (compound of Exemplified Compound No. 1-632)
Using 4-fluoroaniline as the building block-A (various amines) of Example 109, the reaction was carried out in the same manner as in Example 109 to obtain the title compound.
MS (APCI, m / z): 463 (M + H) ⁺ .
HPLC; Rt = 6.01 min.

(Example 113)
N- (3,4-Dihydro-2H-benzo [b] [1,4] dioxepin-7-yl) -2- [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) Amino] acetamide (compound of Exemplified Compound No. 1-669)
The reaction was carried out in the same manner as in Example 109 using 3,4-dihydro-2H-benzo [b] [1,4] dioxepin-7-amine as the building block-A (various amines) in Example 109. A compound was obtained.
MS (APCI, m / z): 517 (M + H) ⁺ .
HPLC; Rt = 5.91 min.

(Example 114)
2- [N- (2,3-Dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- (p-tolyl) acetamide (compound of Exemplified Compound No. 1-23)
The title compound was obtained in the same manner as in Example 109 using p-toluidine as the building block-A (various amines) of Example 109.
MS (APCI, m / z): 459 (M + H) ^<+> .
HPLC; Rt = 6.28min.

(Example 115)
2- [N- (2,3-Dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- (4-methoxyphenyl) acetamide (compound of Exemplified Compound No. 1-52)
The reaction was conducted in the same manner as in Example 109 using p-anisidine for building block-A (various amines) in Example 109 to obtain the title compound.
MS (APCI, m / z): 475 (M + H) ⁺ .
HPLC; Rt = 5.81min.

(Example 116)
2- [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- (3-nitrophenyl) acetamide (compound of exemplary compound number 1-625)
The title compound was obtained by reacting in the same manner as in Example 109 using 3-nitroaniline as the building block-A (various amines) in Example 109.
MS (APCI, m / z): 490 (M + H) ⁺ .
HPLC; Rt = 6.04min.

(Example 117)
2- [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- (4-nitrophenyl) acetamide (compound of exemplary compound number 1-626)
Using 4-nitroaniline as the building block-A (various amines) of Example 109, the reaction was carried out in the same manner as in Example 109 to obtain the title compound.
MS (APCI, m / z): 490 (M + H) ⁺ .
HPLC; Rt = 6.00min.

(Example 118)
3- [2- [N- (2,3-Dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetylamino] benzoic acid ethyl ester (compound of Exemplified Compound No. 1-608)
The title compound was obtained by reacting in the same manner as in Example 109, using 3-aminobenzoic acid ethyl ester for building block-A (various amines) in Example 109.
MS (APCI, m / z): 517 (M + H) ⁺ .
HPLC; Rt = 6.28min.

(Example 119)
4- [2- [N- (2,3-Dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetylamino] benzoic acid ethyl ester (compound of Exemplified Compound No. 1-609)
The title compound was obtained by reacting in the same manner as in Example 109, using 4-aminobenzoic acid ethyl ester for building block-A (various amines) in Example 109.
MS (APCI, m / z): 517 (M + H) ⁺ .
HPLC; Rt = 6.35min.

(Example 120)
2- [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- (3,4,5-trimethoxyphenyl) acetamide (compound of exemplary compound number 1-713)
Reaction was carried out in the same manner as in Example 109 using 3,4,5-trimethoxyaniline for building block-A (various amines) of Example 109 to obtain the title compound.
MS (APCI, m / z): 535 (M + H) ⁺ .
HPLC; Rt = 5.58min.

(Example 121)
2- [N- (2,3-Dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- (4-methoxy-3-trifluoromethylphenyl) acetamide (Compound of Exemplified Compound No. 1-682) )
The title compound was obtained in the same manner as in Example 109 using 3-amino-6-methoxybenzotrifluoride for building block-A (various amines) of Example 109.
MS (APCI, m / z): 543 (M + H) ⁺ .
HPLC; Rt = 6.37min.

(Example 122)
N- (4-Chlorophenyl) -2- [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetamide (compound of Exemplified Compound No. 1-635)
Using 4-chloroaniline as the building block-A (various amines) of Example 109, the reaction was carried out in the same manner as in Example 109 to obtain the title compound.
MS (APCI, m / z): 479 (M + H) ⁺ , 481 (M + H) ⁺ .
HPLC; Rt = 6.47min.

(Example 123)
N- (3,5-dichlorophenyl) -2- [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetamide (compound of exemplary compound number 1-712)
Using 3,5-dichloroaniline for building block-A (various amines) of Example 109, the reaction was carried out in the same manner as in Example 109 to obtain the title compound.
MS (APCI, m / z): 513 (M + H) ⁺ , 515 (M + H) ⁺ .
HPLC; Rt = 7.16min.

(Example 124)
N- (3-chlorophenyl) -2- [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetamide (compound of Exemplified Compound No. 1-634)
The title compound was obtained by reacting in the same manner as in Example 109 using 3-chloroaniline as the building block-A (various amines) in Example 109.
MS (APCI, m / z): 479 (M + H) ⁺ , 481 (M + H) ⁺ .
HPLC; Rt = 6.52min.

(Example 125)
N- (3,4-dichlorophenyl) -2- [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetamide (compound of exemplary compound number 1-711)
Reaction was carried out in the same manner as in Example 109 using 3,4-dichloroaniline for building block-A (various amines) of Example 109 to obtain the title compound.
MS (APCI, m / z): 513 (M + H) ⁺ , 515 (M + H) ⁺ .
HPLC; Rt = 6.95 min.

(Example 126)
2- [N- (2,3-Dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- (3-fluoro-4-methoxyphenyl) acetamide (compound of Exemplified Compound No. 1-700)
The title compound was obtained in the same manner as in Example 109 by using 3-fluoro-4-methoxyaniline for building block-A (various amines) in Example 109.
MS (APCI, m / z): 493 (M + H) ⁺ .
HPLC; Rt = 5.91 min.

(Example 127)
N- (3,5-dimethylphenyl) -2- [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetamide (compound of exemplary compound number 1-678)
The reaction was conducted in the same manner as in Example 109 using 3,5-dimethylaniline for building block-A (various amines) in Example 109 to obtain the title compound.
MS (APCI, m / z): 473 (M + H) ⁺ .
HPLC; Rt = 6.62min.

(Example 128)
2- [N- (2,3-Dimethylphenyl) -N- (naphthalen-1-sulfonyl) amino] -N- (naphthalen-1-yl) acetamide (compound of exemplary compound number 1-1050)
The title compound was obtained in the same manner as in Example 109 by using 1-aminonaphthalene for building block-A (various amines) in Example 109.
MS (APCI, m / z): 495 (M + H) ⁺ .
HPLC; Rt = 6.36min.

(Example 129)
2- [N- (2,3-Dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- (3-trifluoromethoxyphenyl) acetamide (compound of exemplary compound number 1-560)
The title compound was obtained in the same manner as in Example 109 by using 3-trifluoromethoxyaniline for building block-A (various amines) of Example 109.
MS (APCI, m / z): 529 (M + H) ⁺ .
HPLC; Rt = 6.41min.

(Example 130)
2- [N- (2,3-Dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- (3-fluorophenyl) acetamide (compound of Exemplified Compound No. 1-631)
The title compound was obtained by reacting in the same manner as in Example 109 using 3-fluoroaniline as the building block-A (various amines) in Example 109.
MS (APCI, m / z): 463 (M + H) ⁺ .
HPLC; Rt = 5.87min.

(Example 131)
N- (3-phenylphenyl) -2- [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetamide (compound of Exemplified Compound No. 1-715)
The title compound was obtained by reacting in the same manner as in Example 109, using 3-aminobiphenyl as the building block-A (various amines) in Example 109.
MS (APCI, m / z): 521 (M + H) ⁺ .
HPLC; Rt = 6.59min.

(Example 132)
N- (2,3-dimethylphenyl) -2- [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetamide (compound of exemplary compound number 1-673)
Using 2,3-dimethylaniline for building block-A (various amines) of Example 109, the reaction was carried out in the same manner as in Example 109 to obtain the title compound.
MS (APCI, m / z): 473 (M + H) ⁺ .
HPLC; Rt = 6.05min.

(Example 133)
2- [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- (2-methoxy-6-methylphenyl) acetamide (compound of Exemplified Compound No. 1-681)
The title compound was obtained in the same manner as in Example 109 using 2-methoxy-6-methylaniline for building block-A (various amines) of Example 109.
MS (APCI, m / z): 489 (M + H) ⁺ .
HPLC; Rt = 5.71min.

(Example 134)
N- (2,6-dimethoxyphenyl) -2- [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetamide (compound of exemplary compound number 1-695)
Using 2,6-dimethoxyaniline for building block-A (various amines) of Example 109, the reaction was carried out in the same manner as in Example 109 to obtain the title compound.
MS (APCI, m / z): 505 (M + H) ⁺ .
HPLC; Rt = 5.37min.

(Example 135)
3- [2- [N- (2,3-Dimethyl-phenyl) -N- (naphthalene-1-sulfonyl) amino] acetylamino] -4-methoxy-benzoic acid methyl ester (compound of Exemplified Compound No. 1-698 )
The title compound was obtained in the same manner as in Example 109 using 3-amino-4-methoxy-benzoic acid methyl ester for building block-A (various amines) in Example 109.
MS (APCI, m / z): 533 (M + H) ⁺ .
HPLC; Rt = 5.90min.

(Example 136)
N- (3,4-dimethylphenyl) -2- [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetamide (compound of Exemplified Compound No. 1-677)
Reaction was carried out in the same manner as in Example 109 using 3,4-dimethylaniline for building block-A (various amines) of Example 109 to obtain the title compound.
MS (APCI, m / z): 473 (M + H) ⁺ .
HPLC; Rt = 6.23min.

(Example 137)
2- [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- (m-tolyl) acetamide (compound of Exemplified Compound No. 1-22)
The title compound was obtained in the same manner as in Example 109 by using m-toluidine for building block-A (various amines) in Example 109.
MS (APCI, m / z): 459 (M + H) ^<+> .
HPLC; Rt = 6.00min.

(Example 138)
N- (2,5-dichlorophenyl) -2- [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetamide (compound of exemplary compound number 1-709)
Using 2,5-dichloroaniline for building block-A (various amines) of Example 109, the reaction was carried out in the same manner as in Example 109 to obtain the title compound.
MS (APCI, m / z): 513 (M + H) ⁺ , 515 (M + H) ⁺ .
HPLC; Rt = 6.89 min.

(Example 139)
2- [N- (2,3-Dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- (quinolin-6-yl) acetamide (compound of Exemplified Compound No. 1-1198)
Using 6-aminoquinoline as the building block -A (various amines) of Example 109, the reaction was carried out in the same manner as in Example 109 to obtain the title compound.
MS (APCI, m / z): 496 (M + H) ⁺ .
HPLC; Rt = 4.33min.

(Example 140)
N- (2,4-dichlorophenyl) -2- [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetamide (compound of exemplary compound number 1-708)
The title compound was obtained in the same manner as in Example 109 using 2,4-dichloroaniline for building block-A (various amines) of Example 109.
MS (APCI, m / z): 513 (M + H) ⁺ , 515 (M + H) ⁺ .
HPLC; Rt = 6.91 min.

(Example 141)
2- [N- (2,3-Dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- (3-phenoxyphenyl) acetamide (Compound No. 1-1047)
Using 3-phenoxyaniline for building block-A (various amines) of Example 109, the reaction was carried out in the same manner as in Example 109 to obtain the title compound.
MS (APCI, m / z): 537 (M + H) ⁺ .
HPLC; Rt = 6.91 min.

(Example 142)
2- [N- (2,3-Dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- (4-phenoxyphenyl) acetamide (compound of Exemplified Compound No. 1-1048)
Using 4-phenoxyaniline for building block-A (various amines) of Example 109, the reaction was carried out in the same manner as in Example 109 to obtain the title compound.
MS (APCI, m / z): 537 (M + H) ⁺ .
HPLC; Rt = 6.83min.

(Example 143)
N- (Benzo [1,3] dioxol-5-yl) -2- [N- (2,3-dimethyl-phenyl) -N- (naphthalene-1-sulfonyl) amino] acetamide (Exemplified Compound No. 1-668 Compound)
Using 3,4-methylenedioxyaniline for building block-A (various amines) of Example 109, the reaction was carried out in the same manner as in Example 109 to obtain the title compound.
MS (APCI, m / z): 489 (M + H) ⁺ .
HPLC; Rt = 5.75min.

(Example 144)
2- [N- (2,3-Dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- (o-tolyl) acetamide (compound of Exemplified Compound No. 1-21)
The title compound was obtained in the same manner as in Example 109 using o-toluidine as the building block-A (various amines) in Example 109.
MS (APCI, m / z): 459 (M + H) ^<+> .
HPLC; Rt = 6.19min.

(Example 145)
2- [N- (2,3-Dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- (3-methoxyphenyl) acetamide (compound of Exemplified Compound No. 1-48)
Using the m-anisidine for Building Block-A (various amines) of Example 109, the reaction was carried out in the same manner as in Example 109 to obtain the title compound.
MS (APCI, m / z): 475 (M + H) ⁺ .
HPLC; Rt = 5.96min.

(Example 146)
N- (2,4-dimethylphenyl) -2- [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetamide (compound of Exemplified Compound No. 1-674)
Using 2,4-dimethylaniline for building block-A (various amines) of Example 109, the reaction was carried out in the same manner as in Example 109 to obtain the title compound.
MS (APCI, m / z): 473 (M + H) ⁺ .
HPLC; Rt = 6.48min.

(Example 147)
N- (2,6-dimethylphenyl) -2- [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetamide (compound of exemplary compound number 1-676)
The reaction was conducted in the same manner as in Example 109 using 2,6-dimethylaniline as the building block-A (various amines) in Example 109 to obtain the title compound.
MS (APCI, m / z): 473 (M + H) ⁺ .
HPLC; Rt = 6.12min.

(Example 148)
2- [N- (2,3-Dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- (4-methoxy-2-methylphenyl) acetamide (compound of exemplary compound number 1-679)
The title compound was obtained in the same manner as in Example 109 by using 4-methoxy-2-methylaniline for building block-A (various amines) in Example 109.
MS (APCI, m / z): 489 (M + H) ⁺ .
HPLC; Rt = 5.93min.

(Example 149)
N- (3,4-dimethoxyphenyl) -2- [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetamide (compound of exemplary compound number 1-696)
Reaction was carried out in the same manner as in Example 109 using 3,4-dimethoxyaniline for building block-A (various amines) of Example 109 to obtain the title compound.
MS (APCI, m / z): 505 (M + H) ⁺ .
HPLC; Rt = 5.50min.

(Example 150)
4- [2- [N- (2,3-Dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetylamino] -2-methoxybenzoic acid methyl ester (compound of Exemplified Compound No. 1-699)
The title compound was obtained by reacting in the same manner as in Example 109 using 4-amino-2-methoxy-benzoic acid methyl ester for building block-A (various amines) in Example 109.
MS (APCI, m / z): 533 (M + H) ⁺ .
HPLC; Rt = 5.63min.

(Example 151)
2- [N- (2,3-Dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] -N-phenylacetamide (compound of Exemplified Compound No. 1-20)
Reaction was carried out in the same manner as in Example 109 using aniline as the building block-A (various amines) in Example 109 to obtain the title compound.
MS (APCI, m / z): 445 (M + H) ⁺ .
HPLC; Rt = 6.00min.

(Example 152)
N- (3-acetylphenyl) -2- [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetamide (compound of exemplary compound number 1-596)
[N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetic acid (20 mg, 0.049 mmol) prepared in Reference Example 1 was dissolved in N, N-dimethylformamide (1.0 ml). 3-aminoacetophenone (10 mg, 0.073 mmol) and 1-hydroxybenzotriazole (8.2 mg, 0.054 mmol) were added and stirred at room temperature for 10 minutes, followed by 1-ethyl-3- (dimethylaminopropyl) carbodiimide hydrochloride (14.1 mg, 0.073 mmol) was added, and the mixture was stirred at 60 ° C. for 20 hours. The reaction mixture was diluted with ethyl acetate and washed with saturated aqueous sodium hydrogen carbonate. The organic layer is simply purified by silica gel filtration using ethyl acetate, the solvent is concentrated under reduced pressure, and the resulting residue is washed with a mixed solvent of n-hexane-diisopropyl ether to obtain the title compound. It was.
MS (APCI, m / z): 487 (M + H) ⁺ .
HPLC; Rt = 5.40min.

(Example 153)
N- (2,5-dimethylphenyl) -2- [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetamide (compound of exemplary compound number 1-675)
Using 2,5-dimethylaniline for building block-A (various amines) of Example 109, the reaction was carried out in the same manner as in Example 109 to obtain the title compound.
MS (APCI, m / z): 473 (M + H) ⁺ .
HPLC; Rt = 6.22min.

(Example 154)
2- [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- (2-trifluoromethylphenyl) acetamide (compound of Exemplified Compound No. 1-30)
The title compound was obtained in the same manner as in Example 109 except that 2-trifluoromethylaniline was used for building block-A (various amines) of Example 109.
MS (APCI, m / z): 513 (M + H) +.
HPLC; Rt = 6.42min.

(Example 155)
2- [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- (2-fluorophenyl) acetamide (compound of exemplary compound number 1-630)
The title compound was obtained in the same manner as in Example 109 using 2-fluoroaniline as the building block-A (various amines) in Example 109.
MS (APCI, m / z): 463 (M + H) ⁺ .
HPLC; Rt = 6.23min.

(Example 156)
2- [N- (2,3-Dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- (2-methoxyphenyl) acetamide (compound of Exemplified Compound No. 1-47)
Using 2-methoxyaniline as the building block of Example 109 (various amines), the reaction was conducted in the same manner as in Example 109 to obtain the title compound.
MS (APCI, m / z): 475 (M + H) +.
HPLC; Rt = 6.39min.

(Example 157)
N- (2-phenylphenyl) -2- [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetamide (compound of Exemplified Compound No. 1-714)
The title compound was obtained by reacting in the same manner as in Example 109 using 2-aminobiphenyl for building block-A (various amines) in Example 109.
MS (APCI, m / z): 521 (M + H) ⁺ .
HPLC; Rt = 7.00min.

(Example 158)
2- [N- (2,3-Dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- (2-methoxy-5-methylphenyl) acetamide (compound of exemplary compound number 1-680)
The title compound was obtained in the same manner as in Example 109 using 2-methoxy-5-methylaniline as the building block-A (various amines) in Example 109.
MS (APCI, m / z): 489 (M + H) ⁺ .
HPLC; Rt = 6.76min.

(Example 159)
N- (2,3-dimethoxyphenyl) -2- [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetamide (compound of Exemplified Compound No. 1-692)
The title compound was obtained in the same manner as in Example 109 using 2,3-dimethoxyaniline for building block-A (various amines) of Example 109.
MS (APCI, m / z): 505 (M + H) +.
HPLC; Rt = 6.46min.

(Example 160)
N- (2-chlorophenyl) -2- [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetamide (compound of exemplary compound number 1-633)
Using 2-chloroaniline for building block-A (various amines) of Example 109, the reaction was carried out in the same manner as in Example 109 to obtain the title compound.
MS (APCI, m / z): 479 (M + H) +, 481 (M + H) ⁺ .
HPLC; Rt = 6.65min.

(Example 161)
2- [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- (3-phenyl-1-propyl) acetamide (compound of Exemplified Compound No. 1-7)
The title compound was obtained by reacting in the same manner as in Example 109 using 3-phenyl-1-propylamine for building block-A (various amines) in Example 109.
MS (APCI, m / z): 487 (M + H) ⁺ .
HPLC; Rt = 6.26min.

(Example 162)
2- [N- (2,3-Dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- (2-phenyl-1-propyl) acetamide (compound of Exemplified Compound No. 1-6)
The title compound was obtained in the same manner as in Example 109 except that 2-phenyl-1-propylamine was used for building block-A (various amines) of Example 109.
MS (APCI, m / z): 487 (M + H) ⁺ .
HPLC; Rt = 6.34min.

(Example 163)
N- (4-hydroxyphenyl) -2- [N- (naphthalene-1-sulfonyl) -N- (3-trifluoromethylphenyl) amino] acetamide (compound of Exemplified Compound No. 1-45)
Using [N- (naphthalene-1-sulfonyl) -N- (3-trifluoromethylphenyl) amino] acetic acid prepared in Reference Example 1 and 4-hydroxyaniline, the reaction was carried out in the same manner as in Example 152, The title compound was obtained.
MS (APCI, m / z): 501 (M + H) ⁺ .
HPLC; Rt = 4.81min.

(Example 164)
N-cyclobutyl-2- [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetamide (compound of Exemplified Compound No. 1-13)
The title compound was obtained in the same manner as in Example 109 except that cyclobutylamine was used for building block-A (various amines) of Example 109.
MS (APCI, m / z): 423 (M + H) ⁺ .
HPLC; Rt = 5.37min.

(Example 165)
N-cyclohexyl-2- [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetamide (compound of Exemplified Compound No. 1-15)
The title compound was obtained in the same manner as in Example 109 except that cyclohexylamine was used for building block-A (various amines) of Example 109.
MS (APCI, m / z): 451 (M + H) ⁺ .
HPLC; Rt = 5.98 min.

(Example 166)
2- [N- (2,3-Dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- (1-heptyl) acetamide (compound of Exemplified Compound No. 1-1)
Using 1-heptylamine as the building block-A (various amines) of Example 109, the reaction was carried out in the same manner as in Example 109 to obtain the title compound.
MS (APCI, m / z): 467 (M + H) ⁺ .
HPLC; Rt = 6.69min.

(Example 167)
N-cyclopropyl-2- [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetamide (compound of Exemplified Compound No. 1-12)
The title compound was obtained in the same manner as in Example 109 except that cyclopropylamine was used for building block-A (a variety of amines) in Example 109.
MS (APCI, m / z): 409 (M + H) ⁺ .
HPLC; Rt = 4.90min.

(Example 168)
2- [2- [N- (2,3-Dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetylamino] benzoic acid ethyl ester (compound of exemplary compound number 1-607)
The title compound was obtained by reacting in the same manner as in Example 109, using 3-aminobenzoic acid ethyl ester for building block-A (various amines) in Example 109.
MS (APCI, m / z): 517 (M + H) ⁺ .
HPLC; Rt = 6.81min.

(Example 169)
N- (4-acetylphenyl) -2- [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetamide (compound of exemplary compound number 1-599)
The reaction was performed in the same manner as in Example 152 using [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetic acid and 4-aminoacetophenone prepared in Reference Example 1. The title compound was obtained.
¹ H-NMR (DMSO-d ₆ ) δ: 10.29 (s, 1H), 8.28 (d like, 2H, J = 8.4Hz), 8.10 (d like, 2H, J = 7.6Hz), 7.89 (d, 2H , J = 8.9Hz), 7.65 (d, 1H, J = 7.6Hz), 7.62 (d, 1H, J = 7.8Hz), 7.60 (d, 2H, J = 8.9Hz), 7.48 (dd like, 1H, J = 8.4, 7.3Hz), 7.11 (dd, 1H, J = 5.7, 3.0Hz), 6.99-6.89 (m, 2H), 4.62 (d, 1H, J = 17.0Hz), 4.37 (d, 1H, J = 17.0Hz), 2.50 (s, 3H), 2.12 (s, 3H), 1.81 (s, 3H).
MS (APCI, m / z): 487 (M + H) ⁺ .
HPLC; Rt = 5.37min.

(Example 170)
4- [2- [N- (2,3-Dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetylamino] piperidine-1-carboxylic acid ethyl ester (compound of Exemplified Compound No. 1-1106)
The title compound was obtained by reacting in the same manner as in Example 109, using 4-amino-1-piperidinecarboxylic acid ethyl ester for building block-A (various amines) in Example 109. MS (APCI, m / z): 524 (M + H) +.
HPLC; Rt = 5.32min.

(Example 171)
N-cyclopentyl-2-[(2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetamide (compound of Exemplified Compound No. 1-14)
The title compound was obtained in the same manner as in Example 109 except that cyclopentylamine was used for building block-A (various amines) of Example 109.

MS (APCI, m / z): 437 (M + H) ⁺ .
HPLC; Rt = 5.84min.

(Example 172)
2- [N- (2,3-Dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- (2-methylcyclohexyl) acetamide (compound of Exemplified Compound No. 1-16)
The title compound was obtained by reacting in the same manner as in Example 109, using 2-methylcyclohexylamine for building block-A (various amines) in Example 109.
MS (APCI, m / z): 465 (M + H) ⁺ .
HPLC; Rt = 6.52min.

(Example 173)
N-cycloheptyl-2- [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetamide (compound of Exemplified Compound No. 1-17)
The title compound was obtained in the same manner as in Example 109 using cycloheptylamine as the building block-A (various amines) of Example 109.
MS (APCI, m / z): 465 (M + H) ⁺ .
HPLC; Rt = 6.58min.

(Example 174)
2- [N- (2,3-Dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- (indan-2-yl) acetamide (compound of Exemplified Compound No. 1-1053)
The title compound was obtained in the same manner as in Example 109 by using 2-aminoindane for building block-A (various amines) of Example 109.
MS (APCI, m / z): 485 (M + H) ⁺ .
HPLC; Rt = 6.17min.

(Example 175)
2- [N- (2,3-Dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- [2- (3-methoxyphenyl) ethyl] acetamide (compound of Exemplified Compound No. 1-5)
The title compound was obtained in the same manner as in Example 109 except that 3-methoxyphenethylamine was used for building block-A (various amines) of Example 109.
MS (APCI, m / z): 503 (M + H) ⁺ .
HPLC; Rt = 6.00min.

(Example 176)
2- [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- (1-methyl-2-phenoxyethyl) acetamide (compound of Exemplified Compound No. 1-9)
Using 1-methyl-2-phenoxyethylamine for building block-A (various amines) of Example 109, the reaction was carried out in the same manner as in Example 109 to obtain the title compound.
MS (APCI, m / z): 503 (M + H) ⁺ .
HPLC; Rt = 6.32min.

(Example 177)
2- [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- (5-methylpyridin-2-yl) acetamide (compound of exemplary compound number 1-1092)
Using [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetic acid and (5-methylpyridin-2-yl) amine prepared in Reference Example 1, The reaction was conducted in the same manner as in 152 to give the title compound.
MS (APCI, m / z): 460 (M + H) ⁺ .
HPLC; Rt = 5.42min.

(Example 178)
2- [N- (2,3-Dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- (6-methoxypyridin-3-yl) acetamide (compound of Exemplified Compound No. 1-1097)
Using [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetic acid and (6-methoxypyridin-3-yl) amine prepared in Reference Example 1, The reaction was conducted in the same manner as in 152 to give the title compound.
MS (APCI, m / z): 476 (M + H) ⁺ .
HPLC; Rt = 5.25min.

(Example 179)
N- (6-chloropyridin-3-yl) -2- [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetamide (compound of Exemplified Compound No. 1-1101)
Using [N- (2,3-dimethylphenyl) -N- (naphthalen-1-sulfonyl) amino] acetic acid and (6-chloropyridin-3-yl) amine prepared in Reference Example 1, The reaction was conducted in the same manner as in 152 to give the title compound.
MS (APCI, m / z): 480 (M + H) ⁺ , 482 (M + H) ⁺ .
HPLC; Rt = 5.48min.

(Example 180)
2- [N- (2,3-Dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- (6-methylpyridin-3-yl) acetamide (compound of Exemplified Compound No. 1-1093)
Using [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetic acid prepared in Reference Example 1 and (6-methyl-pyridin-3-yl) amine The reaction was conducted in the same manner as in Example 152 to obtain the title compound.
¹ H-NMR (DMSO-d ₆ ) δ: 10.01 (s, 1H), 8.44 (d, 1H, J = 2.7Hz), 8.30 (d, 1H, J = 4.3Hz), 8.27 (d, 1H, J = 3.8Hz), 8.09 (d like, 2H, J = 7.6Hz), 7.78 (dd, 1H, J = 8.4, 2.7Hz), 7.64 (d, 1H, J = 7.8Hz), 7.62 (d, 1H, J = 7.6Hz), 7.48 (ddd, 1H, J = 8.4, 6.9, 1.5Hz), 7.15 (d, 1H, J = 8.4Hz), 7.10 (dd, 1H, J = 4.9, 4.3Hz), 6.93 ( d like, 2H, J = 4.9Hz), 4.58 (d, 1H, J = 16.6Hz), 4.34 (d, 1H, J = 16.6Hz), 2.38 (s, 3H), 2.13 (s, 3H), 1.82 (s, 3H).
MS (APCI, m / z): 460 (M + H) ⁺ .
HPLC; Rt = 3.88min.

(Example 181)
Naphthalene-1-sulfonic acid [N- (2,3-dimethylphenyl) -N- [2- (4-methoxyphenyl) -2-oxoethyl]] amide (compound of Exemplified Compound No. 2-8)
Naphthalene-1-sulfonic acid [N- (2,3-dimethylphenyl)] amide (24 mg, 0.077 mmol) prepared in Reference Example 2 was dissolved in N, N-dimethylformamide (1.0 ml), and 4′- Methoxyphenacyl bromide (23 mg, 0.10 mmol) and potassium carbonate (32 mg, 0.23 mmol) were added, and the mixture was stirred at room temperature for 18 hours. The reaction mixture was diluted with ethyl acetate and washed with saturated aqueous sodium hydrogen carbonate. The organic layer was simply purified by silica gel filtration using ethyl acetate, the solvent was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (elution solvent: hexane / ethyl acetate = 1/1). The title compound was obtained by purification.
MS (APCI, m / z): 460 (M + H) ⁺ .
HPLC; Rt = 6.50min.

(Example 182)
Naphthalene-1-sulfonic acid [N- (2,3-dimethylphenyl) -N- [2- (naphthalen-2-yl) -2-oxoethyl]] amide (compound of Exemplified Compound No. 2-187)
Using the naphthalene-1-sulfonic acid [N- (2,3-dimethylphenyl)] amide prepared in Reference Example 2 and 2-bromoacetylnaphthalene, the reaction was carried out in the same manner as in Example 181 to obtain the title compound. Obtained.
MS (APCI, m / z): 480 (M + H) ⁺ .
HPLC; Rt = 7.19 min.

(Example 183)
Naphthalene-1-sulfonic acid [N- [2- (2,5-dimethoxyphenyl) -2-oxoethyl] -N- (2,3-dimethyl-phenyl)] amide (compound of exemplified compound number 2-70)
In the same manner as in Example 181, using naphthalene-1-sulfonic acid [N- (2,3-dimethylphenyl)] amide prepared in Reference Example 2 and 2-bromo-2 ′, 5′-dimethoxyacetophenone. Reaction was performed to obtain the title compound.
MS (APCI, m / z): 490 (M + H) ⁺ .
HPLC; Rt = 6.75min.

(Example 184)
Naphthalene-1-sulfonic acid [N- [2- (2,4-dimethoxyphenyl) -2-oxoethyl] -N- (2,3-dimethylphenyl)] amide (compound No. 2-69)
In the same manner as in Example 181, using naphthalene-1-sulfonic acid [N- (2,3-dimethylphenyl)] amide prepared in Reference Example 2 and 2-bromo-2 ′, 4′-dimethoxyacetophenone. Reaction was performed to obtain the title compound.
MS (APCI, m / z): 490 (M + H) +.
HPLC; Rt = 6.68min.

(Example 185)
Naphthalene-1-sulfonic acid [N- (2,3-dimethylphenyl) -N- [2- (3-methoxyphenyl) -2-oxoethyl]] amide (compound of Exemplified Compound No. 2-7)
The reaction was conducted in the same manner as in Example 181 using naphthalene-1-sulfonic acid [N- (2,3-dimethylphenyl)] amide prepared in Reference Example 2 and 2-bromo-3′-methoxyacetophenone. The title compound was obtained.
MS (APCI, m / z): 460 (M + H) +.
HPLC; Rt = 6.61min.

(Example 186)
Naphthalene-1-sulfonic acid [N- [2- (4-chlorophenyl) -2-oxoethyl] -N- (2,3-dimethylphenyl)] amide (compound of Exemplified Compound No. 2-65)
The reaction was conducted in the same manner as in Example 181 using naphthalene-1-sulfonic acid [N- (2,3-dimethylphenyl)] amide prepared in Reference Example 2 and 2-bromo-4′-chloroacetophenone. The title compound was obtained.
MS (APCI, m / z): 464 (M + H) ⁺ .
HPLC; Rt = 7.05min.

(Example 187)
Naphthalene-1-sulfonic acid [N- [2- (2,3-dihydrobenzo [1,4] dioxin-6-yl) -2-oxoethyl] -N- (2,3-dimethylphenyl)] amide (example) Compound No. 2-66)
Similar to Example 181 using naphthalene-1-sulfonic acid [N- (2,3-dimethylphenyl)] amide and 3,4- (ethylenedioxy) phenacyl bromide prepared in Reference Example 2. Reaction was performed to obtain the title compound.
MS (APCI, m / z): 488 (M + H) ⁺ .
HPLC; Rt = 6.39min.

(Example 188)
Naphthalene-1-sulfonic acid [N- [2- (3,4-dihydro-2H-benzo [b] [1,4] dioxepin-7-yl) -2-oxoethyl] -N- (2,3-dimethyl Phenyl)] amide (Exemplary Compound No. 2-67)
Similar to Example 181 using naphthalene-1-sulfonic acid [N- (2,3-dimethylphenyl)] amide and 3,4- (trimethylenedioxy) phenacyl bromide prepared in Reference Example 2. To give the title compound.
MS (APCI, m / z): 502 (M + H) ⁺ .
HPLC; Rt = 6.64min.

(Example 189)
Naphthalene-1-sulfonic acid [N- (2,3-dimethylphenyl) -N- [2- (2-methoxyphenyl) -2-oxoethyl]] amide (compound of Exemplified Compound No. 2-6)
The reaction was conducted in the same manner as in Example 181 using naphthalene-1-sulfonic acid [N- (2,3-dimethylphenyl)] amide prepared in Reference Example 2 and 2-bromo-2′-methoxyacetophenone. The title compound was obtained.
MS (APCI, m / z): 460 (M + H) ⁺ .
HPLC; Rt = 6.73 min.

(Example 190)
Naphthalene-1-sulfonic acid [N- (2,3-dimethylphenyl) -N- [2-oxo-2- (p-tolyl) ethyl]] amide (compound of Exemplified Compound No. 2-2)
The reaction was conducted in the same manner as in Example 181 using naphthalene-1-sulfonic acid [N- (2,3-dimethylphenyl)] amide prepared in Reference Example 2 and 2-bromo-4′-methylacetophenone. The title compound was obtained.
MS (APCI, m / z): 444 (M + H) ⁺ .
HPLC; Rt = 6.90min.

(Example 191)
2- [N- (2,3-Dimethylphenyl) -N- (phenylmethanesulfonyl) amino] -N- (4-ethoxyphenyl) acetamide (compound of Exemplified Compound No. 1-231)
Dissolve 2,3-dimethylaniline (18 mg, 0.15 mmol) in dichloromethane (0.8 ml), add phenylmethanesulfonyl chloride (19 mg, 0.10 mmol), cool to 0 ° C, and then pyridine (0.012 ml, 0.15 mmol). ) And 4- (dimethylamino) pyridine (catalytic amount, about 2 mg) were added, and the mixture was stirred for 20 hours while slowly warming from 0 ° C. to room temperature. The reaction mixture was diluted with dichloromethane and washed with water, saturated aqueous sodium hydrogen carbonate, and saturated brine. The organic layer is dried over anhydrous sodium sulfate and purified by simple silica gel filtration using ethyl acetate, and the solvent is concentrated under reduced pressure to obtain N- (2,3-dimethylphenyl) phenylmethanesulfonamide. It was. This compound was used in the next reaction without purification.

The obtained N- (2,3-dimethylphenyl) phenylmethanesulfonamide was dissolved in N, N-dimethylformamide (1.0 ml) and 2-bromo-N- (4-ethoxyphenyl) produced in Reference Example 7 was prepared. Acetamide (38 mg, 0.15 mmol) and potassium carbonate (55 mg, 0.40 mmol) were added, and the mixture was stirred at room temperature for 16 hours. The reaction mixture was diluted with ethyl acetate and washed with saturated aqueous sodium hydrogen carbonate. The organic layer was simply purified by silica gel filtration using ethyl acetate, the solvent was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (elution solvent: hexane / ethyl acetate = 2/1). After purification and concentration, the obtained residue was washed with a mixed solvent of n-hexane-diisopropyl ether to obtain the title compound.
MS (APCI, m / z): 453 (M + H) ⁺ .
HPLC; Rt = 5.75min.

(Example 192)
2- [N- (2,3-Dimethylphenyl) -N- (4-fluoronaphthalene-1-sulfonyl) amino] -N- [4- (4-methyl-5-thioxo-4,5-dihydro-1H -[1,2,4] Triazol-3-yl) phenyl] acetamide (compound of Exemplified Compound No. 1-1044)
[N- (2,3-dimethylphenyl) -N- (4-fluoronaphthalene-1-sulfonyl) amino] acetic acid prepared in Reference Example 22 and 5- (4-aminophenyl) prepared in Reference Example 16 The title compound was obtained in the same manner as in Example 152 using 4-methyl-2,4-dihydro- [1,2,4] triazole-3-thione.
MS (APCI, m / z): 576 (M + H) ⁺ .
HPLC; Rt = 5.14min.

(Example 193)
2- [N- (5-Bromo-6-chloropyridine-3-sulfonyl) -N- (2,3-dimethylphenyl) amino] -N- (4-ethoxyphenyl) acetamide (Exemplary Compound No. 1-319 Compound)
The title compound was obtained in the same manner as in Example 191 using 3-bromo-2-chloropyridine-5-sulfonyl chloride.
MS (APCI, m / z): 552 (M + H) ⁺ , 554 (M + H) ⁺ , 556 (M + H) ⁺ .
HPLC; Rt = 6.45min.

(Example 194)
2- [N- (2,3-dimethylphenyl) -N- (2,4,6-trimethylbenzenesulfonyl) amino] -N- (4-ethoxyphenyl) acetamide (compound of Exemplified Compound No. 1-284)
This group of compounds was synthesized by using the encoding synthesis method by IRORI's MiniKans (registered trademark). 48 MiniKan identified by RF tag were each 2- (3,5-dimethoxy-4-formylphenoxy) ethoxymethyl polystyrene resin (Novabiochem, 0.90 mmol / g; 105 mg × 48 pieces = 5.04 g, 4.54 All of the microreactors encapsulating mmol) were swollen together in N, N-dimethylacetamide-acetic acid (9: 1, 200 ml). Magnesium sulfate (596 mg, 4.95 mmol) and p-phenetidine (7.256 ml, 56.3 mmol) were added, and the mixture was heated and stirred at 80 ° C. for 1 hour under a nitrogen atmosphere. Thereafter, sodium triacetoxyborohydride (11.9 g, 56.3 mmol) was added to the reaction system, and the mixture was heated and stirred at 80 ° C. for 24 hours. The reaction system was cooled to room temperature, and the resin was washed several times with warm water, N, N-dimethylformamide, tetrahydrofuran, methanol, and dichloromethane, washed with diethyl ether, and dried under reduced pressure.

  Next, all microreactors (0.90 mmol / g; 105 mg × 48, 4.54 mmol) were swollen in N, N-dimethylacetamide (230 ml), cooled to 0 ° C. under a nitrogen atmosphere, and then brominated with bromide. Acetyl (3.923 ml, 45.0 mmol) was added over 3 minutes, and the mixture was stirred for 24 hours while slowly warming from 0 ° C. to room temperature. Thereafter, the resin was washed several times with N, N-dimethylformamide, tetrahydrofuran, methanol, and dichloromethane, and then washed with diethyl ether and dried under reduced pressure.

  Subsequently, all microreactors (0.90 mmol / g; 105 mg x 48, 4.54 mmol) were swollen in dimethyl sulfoxide (160 ml), 2,3-dimethylaniline (8.24 ml, 67.5 mmol) was added, and the mixture Was stirred for 22 hours at 80 ° C. in a nitrogen atmosphere. The reaction system was cooled to room temperature, and the resin was washed several times with N, N-dimethylformamide, tetrahydrofuran, methanol and dichloromethane, then with diethyl ether and dried under reduced pressure.

  Subsequently, after dividing the microreactor into 48 types according to the instructions of the RF tag, the microreactor (0.90 mmol / g; 105 mg × 1 piece, 0.094 mmol) was swollen in pyridine (4.0 ml), and the building block − C (various sulfonyl chlorides) [eg 2-mesitylenesulfonyl chloride (218 mg, 1.0 mmol)] and 4- (dimethylamino) pyridine (catalytic amount, about 2 mg) are added and the mixture is placed at 70 ° C. under nitrogen atmosphere. The mixture was heated and stirred for 19 hours. The reaction system was cooled to room temperature, and all the microreactors that reacted separately were combined. The resin was washed several times with tetrahydrofuran, methanol, and dichloromethane, then washed with diethyl ether, and dried under reduced pressure.

Subsequently, after dividing these microreactors into 48 types according to the instructions of the RF tag, each microreactor was treated with 25% trifluoroacetic acid in dichloromethane for 15 hours, concentrated and then subjected to appropriate purification operations to obtain the title compound. Obtained.
MS (APCI, m / z): 481 (M + H) ⁺ .
HPLC; Rt = 6.62min.

(Example 195)
2- [N- (2,4-Difluorobenzenesulfonyl) -N- (2,3-dimethylphenyl) amino] -N- (4-ethoxyphenyl) acetamide (compound of Exemplified Compound No. 1-271)
The title compound was obtained in the same manner as in Example 194 by using 2,4-difluorobenzenesulfonyl chloride as the building block -C (various sulfonyl chlorides) in Example 194.
MS (APCI, m / z): 475 (M + H) ⁺ .
HPLC; Rt = 5.68min.

(Example 196)
2- [N- (4-Chloro-2,5-dimethylbenzenesulfonyl) -N- (2,3-dimethylphenyl) amino] -N- (4-ethoxyphenyl) acetamide (Compound No. 1-285) )
The title compound was obtained by reacting in the same manner as in Example 194 using 4-chloro-2,5-dimethylbenzenesulfonyl chloride for building block -C (various sulfonyl chlorides) in Example 194.
MS (APCI, m / z): 501 (M + H) ⁺ , 503 (M + H) ⁺ .
HPLC; Rt = 6.83min.

(Example 197)
2- [N- (2,5-dichlorobenzenesulfonyl) -N- (2,3-dimethylphenyl) amino] -N- (4-ethoxyphenyl) acetamide (compound with exemplary compound number 1-280)
Using 2,5-dichlorobenzenesulfonyl chloride for the building block -C (various sulfonyl chlorides) of Example 194, the reaction was carried out in the same manner as in Example 194 to obtain the title compound.
MS (APCI, m / z): 507 (M + H) ⁺ , 509 (M + H) ⁺ .
HPLC; Rt = 6.25min.

(Example 198)
2- [N- (2,3-Dimethylphenyl) -N- (5-fluoro-2-methylbenzenesulfonyl) amino] -N- (4-ethoxyphenyl) acetamide (compound of Exemplified Compound No. 1-257)
Using the 5-fluoro-2-methylbenzenesulfonyl chloride as the building block -C (various sulfonyl chlorides) of Example 194, the reaction was carried out in the same manner as in Example 194 to obtain the title compound.
MS (APCI, m / z): 471 (M + H) ⁺ .
HPLC; Rt = 6.03min.

(Example 199)
2- [N- (2,3-Dimethylphenyl) -N- (2-methoxy-4-methylbenzenesulfonyl) amino] -N- (4-ethoxyphenyl) acetamide (Compound No. 1-254)
Using the 2-methoxy-4-methylbenzenesulfonyl chloride for the building block -C (various sulfonyl chlorides) of Example 194, the reaction was carried out in the same manner as in Example 194 to obtain the title compound.
MS (APCI, m / z): 483 (M + H) ^<+> .
HPLC; Rt = 5.64min.

(Example 200)
2- [N- (3-Chloro-2-methylbenzenesulfonyl) -N- (2,3-dimethylphenyl) amino] -N- (4-ethoxyphenyl) -acetamide (compound of Exemplified Compound No. 1-258)
Using the 3-chloro-2-methylbenzenesulfonyl chloride for the building block -C (various sulfonyl chlorides) of Example 194, the reaction was carried out in the same manner as in Example 194 to obtain the title compound.
MS (APCI, m / z): 487 (M + H) ⁺ , 489 (M + H) ₊ .
HPLC; Rt = 6.49min.

(Example 201)
2- [N- (2-Chloro-6-methylbenzenesulfonyl) -N- (2,3-dimethylphenyl) amino] -N- (4-ethoxyphenyl) acetamide (compound of Exemplified Compound No. 1-259)
Using the 2-chloro-6-methylbenzenesulfonyl chloride for the building block -C (various sulfonyl chlorides) of Example 194, the reaction was carried out in the same manner as in Example 194 to obtain the title compound.
MS (APCI, m / z): 487 (M + H) ⁺ , 489 (M + H) ⁺ .
HPLC; Rt = 6.07min.

(Example 202)
2- [N- (2-Chloro-4-fluorobenzenesulfonyl) -N- (2,3-dimethylphenyl) amino] -N- (4-ethoxyphenyl) acetamide (compound of exemplary compound number 1-276)
Using the 2-chloro-4-fluorobenzenesulfonyl chloride for the building block -C (various sulfonyl chlorides) of Example 194, the reaction was carried out in the same manner as in Example 194 to obtain the title compound.
MS (APCI, m / z): 491 (M + H) ⁺ , 493 (M + H) ⁺ .
HPLC; Rt = 5.89min.

(Example 203)
2- [N- (2,3-dimethylphenyl) -N- (2,3,5,6-tetramethylbenzenesulfonyl) amino] -N- (4-ethoxyphenyl) acetamide (Exemplary Compound No. 1-289 Compound)
Using 2,3,5,6-tetramethylbenzenesulfonyl chloride for the building block -C (various sulfonyl chlorides) of Example 194, the reaction was carried out in the same manner as in Example 194 to obtain the title compound.
MS (APCI, m / z): 495 (M + H) ⁺ .
HPLC; Rt = 6.81min.

(Example 204)
2- [N- (2,3-Dimethylphenyl) -N- (4-methyl-3-nitro-benzenesulfonyl) amino] -N- (4-ethoxyphenyl) acetamide (compound of Exemplified Compound No. 1-256)
The title compound was obtained in the same manner as in Example 194 using 4-methyl-3-nitrobenzenesulfonyl chloride as the building block -C (various sulfonyl chlorides) in Example 194.
MS (APCI, m / z): 498 (M + H) ⁺ .
HPLC; Rt = 5.87min.

(Example 205)
2- [N- (2,3-Dimethylphenyl) -N- (2-methyl-5-nitrobenzenesulfonyl) amino] -N- (4-ethoxyphenyl) acetamide (Compound No. 1-255)
The title compound was obtained in the same manner as in Example 194 using 2-methyl-5-nitrobenzenesulfonyl chloride as the building block -C (various sulfonyl chlorides) in Example 194.
MS (APCI, m / z): 498 (M + H) ⁺ .
HPLC; Rt = 5.90min.

(Example 206)
2- [N- (2,5-dimethoxybenzenesulfonyl) -N- (2,3-dimethylphenyl) amino] -N- (4-ethoxyphenyl) acetamide (compound of Exemplified Compound No. 1-264)
The building block -C (various sulfonyl chlorides) of Example 194 was reacted in the same manner as in Example 194 using 2,5-dimethoxybenzenesulfonyl chloride to obtain the title compound.
MS (APCI, m / z): 499 (M + H) ⁺ .
HPLC; Rt = 5.42min.

(Example 207)
2- [N- (2,6-dichlorobenzenesulfonyl) -N- (2,3-dimethylphenyl) amino] -N- (4-ethoxyphenyl) acetamide (compound of exemplary compound number 1-281)
The building block -C (various sulfonyl chlorides) of Example 194 was reacted in the same manner as in Example 194 using 2,6-dichlorobenzenesulfonyl chloride to obtain the title compound.
MS (APCI, m / z): 507 (M + H) ⁺ , 509 (M + H) ⁺ .
HPLC; Rt = 5.88min.

(Example 208)
2- [N- (2,4-dichlorobenzenesulfonyl) -N- (2,3-dimethylphenyl) amino] -N- (4-ethoxyphenyl) acetamide (compound of Exemplified Compound No. 1-279)
The title compound was obtained in the same manner as in Example 194 by using 2,4-dichlorobenzenesulfonyl chloride for building block -C (various sulfonyl chlorides) in Example 194.
MS (APCI, m / z): 507 (M + H) ⁺ , 509 (M + H) ⁺ .
HPLC; Rt = 6.33min.
(Example 209)
2- [N- (4-acetylamino-3-chlorobenzenesulfonyl) -N- (2,3-dimethylphenyl) amino] -N- (4-ethoxyphenyl) acetamide (compound of Exemplified Compound No. 1-269)
Using the 4-acetylamino-3-chlorobenzenesulfonyl chloride for the building block -C (various sulfonyl chlorides) of Example 194, the reaction was carried out in the same manner as in Example 194 to obtain the title compound.
MS (APCI, m / z): 530 (M + H) ⁺ , 532 (M + H) ⁺ .
HPLC; Rt = 5.16min.

(Example 210)
2- [N- (2,3-Dimethylphenyl) -N- (2,4,6-triisopropylbenzenesulfonyl) amino] -N- (4-ethoxyphenyl) acetamide (Compound No. 1-288)
Using 2,4,6-triisopropylbenzenesulfonyl chloride for building block -C (various sulfonyl chlorides) of Example 194, the reaction was carried out in the same manner as in Example 194 to obtain the title compound.
MS (APCI, m / z): 565 (M + H) ⁺ .
HPLC; Rt = 8.05min.

(Example 211)
2- [N- (3,4-difluorobenzenesulfonyl) -N- (2,3-dimethylphenyl) amino] -N- (4-ethoxyphenyl) acetamide (compound of Exemplified Compound No. 1-274)
The title compound was obtained by reacting in the same manner as in Example 194 using 3,4-difluorobenzenesulfonyl chloride for building block -C (various sulfonyl chlorides) in Example 194.
MS (APCI, m / z): 475 (M + H) ⁺ .
HPLC; Rt = 5.91 min.

(Example 212)
2- [N- (2,3-dichlorobenzenesulfonyl) -N- (2,3-dimethylphenyl) amino] -N- (4-ethoxyphenyl) acetamide (compound of Exemplified Compound No. 1-278)
Using 2,3-dichlorobenzenesulfonyl chloride for the building block -C (various sulfonyl chlorides) of Example 194, the reaction was carried out in the same manner as in Example 194 to obtain the title compound.
MS (APCI, m / z): 507 (M + H) ⁺ , 509 (M + H) ⁺ .
HPLC; Rt = 6.14min.

(Example 213)
2- [N- (4-Bromo-2-methylbenzenesulfonyl) -N- (2,3-dimethylphenyl) amino] -N- (4-ethoxyphenyl) acetamide (Compound No. 1-260)
Using the 4-bromo-2-methylbenzenesulfonyl chloride for the building block -C (various sulfonyl chlorides) of Example 194, the reaction was carried out in the same manner as in Example 194 to obtain the title compound.
MS (APCI, m / z): 531 (M + H) ⁺ , 533 (M + H) ⁺ .
HPLC; Rt = 6.60min.

(Example 214)
2- [N- (4-Bromo-2-ethylbenzenesulfonyl) -N- (2,3-dimethylphenyl) amino] -N- (4-ethoxyphenyl) acetamide (compound of Exemplified Compound No. 1-261)
The title compound was obtained by reacting in the same manner as in Example 194 using 4-bromo-2-ethylbenzenesulfonyl chloride for building block -C (various sulfonyl chlorides) in Example 194.
MS (APCI, m / z): 545 (M + H) ⁺ , 547 (M + H) ⁺ .
HPLC; Rt = 6.84min.

(Example 215)
2- [N- (5-Bromo-2-methoxybenzenesulfonyl) -N- (2,3-dimethylphenyl) amino] -N- (4-ethoxyphenyl) acetamide (compound of exemplary compound number 1-268)
The title compound was obtained by reacting in the same manner as in Example 194 using 5-bromo-2-methoxybenzenesulfonyl chloride as the building block -C (various sulfonyl chlorides) of Example 194.
MS (APCI, m / z): 547 (M + H) ⁺ , 549 (M + H) ⁺ .
HPLC; Rt = 5.95min.

(Example 216)
2- [N- (3,4-dimethoxybenzenesulfonyl) -N- (2,3-dimethylphenyl) amino] -N- (4-ethoxyphenyl) acetamide (compound of Exemplified Compound No. 1-265)
The title compound was obtained by reacting in the same manner as in Example 194 using 3,4-dimethoxybenzenesulfonyl chloride for building block -C (various sulfonyl chlorides) in Example 194.
MS (APCI, m / z): 499 (M + H) ⁺ .
HPLC; Rt = 5.32min.

(Example 217)
2- [N- (3,4-dichlorobenzenesulfonyl) -N- (2,3-dimethylphenyl) amino] -N- (4-ethoxyphenyl) acetamide (compound of Exemplified Compound No. 1-282)
The title compound was obtained in the same manner as in Example 194 by using 3,4-dichlorobenzenesulfonyl chloride for building block -C (various sulfonyl chlorides) in Example 194.
MS (APCI, m / z): 507 (M + H) ⁺ , 509 (M + H) ⁺ .
HPLC; Rt = 6.60min.

(Example 218)
2- [N- (3,5-dichlorobenzenesulfonyl) -N- (2,3-dimethylphenyl) amino] -N- (4-ethoxyphenyl) acetamide (compound of Exemplified Compound No. 1-283)
Using 3,5-dichlorobenzenesulfonyl chloride for the building block -C (various sulfonyl chlorides) of Example 194, the reaction was carried out in the same manner as in Example 194 to obtain the title compound.
MS (APCI, m / z): 507 (M + H) ⁺ , 509 (M + H) ⁺ .
HPLC; Rt = 6.75min.

(Example 219)
2- [N- (2,3-Dimethylphenyl) -N- (4-methoxy-2-nitrobenzenesulfonyl) amino] -N- (4-ethoxyphenyl) acetamide (compound of Exemplified Compound No. 1-266)
The title compound was obtained by reacting in the same manner as in Example 194 using 4-methoxy-2-nitrobenzensulfonyl chloride for building block -C (various sulfonyl chlorides) in Example 194.
MS (APCI, m / z): 514 (M + H) ⁺ .
HPLC; Rt = 5.64min.

(Example 220)
2- [N- (2-Chloro-4-trifluoromethylbenzenesulfonyl) -N- (2,3-dimethylphenyl) amino] -N- (4-ethoxyphenyl) acetamide (Compound No. 1-263) )
Using the 2-chloro-4-trifluoromethylbenzenesulfonyl chloride for the building block -C (various sulfonyl chlorides) of Example 194, the reaction was carried out in the same manner as in Example 194 to obtain the title compound.
MS (APCI, m / z): 541 (M + H) ⁺ , 543 (M + H) ⁺ .
HPLC; Rt = 6.42min.

(Example 221)
2- [N- (2,6-difluorobenzenesulfonyl) -N- (2,3-dimethylphenyl) amino] -N- (4-ethoxyphenyl) acetamide (compound of Exemplified Compound No. 1-273)
Using 2,6-difluorobenzenesulfonyl chloride for the building block -C (various sulfonyl chlorides) of Example 194, the reaction was carried out in the same manner as in Example 194 to obtain the title compound.
MS (APCI, m / z): 475 (M + H) ⁺ .
HPLC; Rt = 5.42min.

(Example 222)
2- [N- (5-Chloro-2-methoxybenzenesulfonyl) -N- (2,3-dimethylphenyl) amino] -N- (4-ethoxyphenyl) acetamide (Compound No. 1-267)
The title compound was obtained in the same manner as in Example 194 using 5-chloro-2-methoxybenzenesulfonyl chloride as the building block -C (various sulfonyl chlorides) in Example 194.
MS (APCI, m / z): 503 (M + H) ⁺ , 505 (M + H) ⁺ .
HPLC; Rt = 5.87min.

(Example 223)
2- [N- (3-Chloro-5-fluoro-2-methylbenzenesulfonyl) -N- (2,3-dimethylphenyl) amino] -N- (4-ethoxyphenyl) acetamide (Exemplified Compound No. 1-286 Compound)
The title compound was obtained by reacting in the same manner as in Example 194, using 3-chloro-5-fluoro-2-methylbenzenesulfonyl chloride for building block -C (various sulfonyl chlorides) in Example 194.
MS (APCI, m / z): 505 (M + H) ⁺ , 507 (M + H) ⁺ .
HPLC; Rt = 6.38min.

(Example 224)
2- [N- (2,4-Dichloro-5-methylbenzenesulfonyl) -N- (2,3-dimethylphenyl) amino] -N- (4-ethoxyphenyl) acetamide (Exemplary Compound No. 1-287 Compound )
Using 2,4-dichloro-5-methylbenzenesulfonyl chloride for the building block -C (various sulfonyl chlorides) of Example 194, the reaction was carried out in the same manner as in Example 194 to obtain the title compound.
MS (APCI, m / z): 521 (M + H) ⁺ , 523 (M + H) ⁺ .
HPLC; Rt = 6.69min.

(Example 225)
2- [N- (3-Chloro-4-fluorobenzenesulfonyl) -N- (2,3-dimethylphenyl) amino] -N- (4-ethoxyphenyl) acetamide (compound of Exemplified Compound No. 1-277)
The title compound was obtained in the same manner as in Example 194 by using 3-chloro-4-fluorobenzenesulfonyl chloride for building block -C (various sulfonyl chlorides) in Example 194.
MS (APCI, m / z): 491 (M + H) ⁺ , 493 (M + H) ⁺ .
HPLC; Rt = 6.21min.

(Example 226)
2- [N- [3,5-bis (trifluoromethyl) benzenesulfonyl] -N- (2,3-dimethylphenyl) amino] -N- (4-ethoxyphenyl) acetamide (Exemplary Compound No. 1-262 Compound)
Using 3,5-bis (trifluoromethyl) benzenesulfonyl chloride for the building block -C (various sulfonyl chlorides) of Example 194, the reaction was carried out in the same manner as in Example 194 to obtain the title compound.
MS (APCI, m / z): 575 (M + H) ⁺ .
HPLC; Rt = 6.89 min.

(Example 227)
N- (4-Ethoxyphenyl) -2- [N- (4-methylpyridin-2-yl) -N- (naphthalene-1-sulfonyl) amino] acetamide (Compound of Exemplified Compound No. 1-436)
2-Amino-4-picoline (10.8 g, 0.10 mmol) was dissolved in dichloromethane (1.0 ml), 1-naphthalenesulfonyl chloride (34 mg, 0.15 mmol) was added, and the mixture was cooled to 0 ° C., and then pyridine (0.012 ml, 0.15 mmol) and 4- (dimethylamino) pyridine (catalytic amount, about 2 mg) were added, and the mixture was stirred for 19 hours while slowly warming from 0 ° C. to room temperature. The reaction mixture was diluted with dichloromethane and washed with water and saturated aqueous sodium hydrogen carbonate. The organic layer was dried over anhydrous sodium sulfate, and then simply purified by silica gel filtration using ethyl acetate. The solvent was concentrated under reduced pressure, and naphthalene-1-sulfonic acid (4-methylpyridin-2-yl) The amide was obtained. This compound was used in the next reaction without purification.
The obtained naphthalene-1-sulfonic acid (4-methylpyridin-2-yl) amide was dissolved in N, N-dimethylformamide (1.0 ml), and 2-bromo-N- (4- Ethoxyphenyl) acetamide (33 mg, 0.13 mmol) and potassium carbonate (55 mg, 0.40 mmol) were added, and the mixture was stirred at room temperature for 23 hours. The reaction mixture was diluted with ethyl acetate and washed with saturated aqueous sodium hydrogen carbonate. The organic layer is simply purified by silica gel filtration using ethyl acetate, the solvent is concentrated under reduced pressure, and the resulting residue is washed with a mixed solvent of n-hexane-ethyl acetate to give the title compound. Got.
MS (APCI, m / z): 476 (M + H) ⁺ .
HPLC; Rt = 4.37min.

(Example 228)
N- (4-Ethoxyphenyl) -2- [N- (5-methylpyridin-2-yl) -N- (naphthalene-1-sulfonyl) amino] acetamide (compound of Exemplified Compound No. 1-437)
The reaction was carried out in the same manner as in Example 227 using 5-methylpyridin-2-ylamine to obtain the title compound.
MS (APCI, m / z): 476 (M + H) ⁺ .
HPLC; Rt = 4.40min.

(Example 229)
N- (4-Ethoxyphenyl) -2- [N- (6-methylpyridin-2-yl) -N- (naphthalene-1-sulfonyl) amino] acetamide (compound of Exemplified Compound No. 1-438)
The reaction was carried out in the same manner as in Example 227 using 6-methylpyridin-2-ylamine to obtain the title compound.
MS (APCI, m / z): 476 (M + H) ⁺ .
HPLC; Rt = 4.38min.

(Example 230)
2- [N- (2,3-Dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- (4-ethynylphenyl) acetamide (compound of Exemplified Compound No. 1-44)
The reaction was conducted in the same manner as in Example 152 using [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetic acid and 4-ethynylaniline prepared in Reference Example 1. The title compound was obtained.
MS (APCI, m / z): 469 (M + H) ⁺ .
HPLC; Rt = 5.90min.

(Example 231)
2- [N- (2,3-Dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- [4- (1-propyl) phenyl] acetamide (compound of Exemplified Compound No. 1-25)
Similar to Example 152, using [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetic acid and 4- (1-propyl) aniline prepared in Reference Example 1. To give the title compound.
MS (APCI, m / z): 487 (M + H) ⁺ .
HPLC; Rt = 6.71 min.

(Example 232)
N- (4-acetylaminophenyl) -2- [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetamide (compound of Exemplified Compound No. 1-591)
The reaction was conducted in the same manner as in Example 152 using [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetic acid and 4-aminoacetanilide prepared in Reference Example 1. The title compound was obtained.
MS (APCI, m / z): 502 (M + H) ⁺ .
HPLC; Rt = 4.68min.

(Example 233)
2- [N- (2,3-Dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- (4-methylsulfanylphenyl) acetamide (compound of Exemplified Compound No. 1-569)
The reaction was conducted in the same manner as in Example 152 using [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetic acid and 4-methylsulfanylaniline prepared in Reference Example 1. And the title compound was obtained.
MS (APCI, m / z): 491 (M + H) ⁺ .
HPLC; Rt = 6.03min.

(Example 234)
4- [2- [N- (2,3-Dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetylamino] benzoic acid tert-butyl ester (compound of Exemplified Compound No. 1-610)
Using [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetic acid and 4-aminobenzoic acid tert-butyl ester prepared in Reference Example 1, Example 152 and The reaction was carried out in the same manner to obtain the title compound.
MS (APCI, m / z): 545 (M + H) ⁺ .
HPLC; Rt = 6.97min.

(Example 235)
4- [2- [N- (2,3-Dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetylamino] benzoic acid (compound of Exemplified Compound No. 1-605)
4- [2- [N- (2,3-Dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetylamino] benzoic acid tert-butyl ester (265 mg, 0.487 mmol) prepared in Example 234 Was dissolved in dichloromethane (2.0 ml) and cooled to 0 ° C., 50% trifluoroacetic acid in dichloromethane (2.0 ml) was added, and the mixture was stirred for 3 hours while slowly warming from 0 ° C. to room temperature. The reaction mixture was diluted with dichloromethane and washed with 1N hydrochloric acid and saturated brine. The organic layer was dried over anhydrous sodium sulfate, the solvent was concentrated under reduced pressure, and the obtained residue was washed with a mixed solvent of n-hexane-diisopropyl ether to obtain the title compound (224 mg, 94%). .
MS (APCI, m / z): 489 (M + H) ⁺ .
HPLC; Rt = 5.03min.

(Example 236)
2- [N- (2,3-Dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- (4-sulfamoylphenyl) acetamide (compound of Exemplified Compound No. 1-577)
Reaction was carried out in the same manner as in Example 152, using [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetic acid and 4-aminobenzenesulfonamide prepared in Reference Example 1. To obtain the title compound.
MS (APCI, m / z): 524 (M + H) ⁺ .
HPLC; Rt = 4.88min.

(Example 237)
2- [N- (2,3-Dimethylphenyl) -N- (3-methylquinoline-8-sulfonyl) amino] -N- (4-ethoxyphenyl) acetamide (compound of Exemplified Compound No. 1-338)
The title compound was obtained in the same manner as in Example 262, using 3-methylquinoline-8-sulfonyl chloride.
MS (APCI, m / z): 504 (M + H) ⁺ .
HPLC; Rt = 5.71min.

(Example 238)
4- [2- [N- (2,3-Dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetylamino] benzamide (compound of Exemplified Compound No. 1-611)
4- [2- [N- (2,3-Dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetylamino] benzoic acid (20 mg, 0.049 mmol) prepared in Example 235 was dissolved in dichloromethane-tetrahydrofuran. After dissolving in (4: 1, 1.3 ml), 1,1′-carbonylbis-1H-imidazole (10 mg, 0.061 mmol) was added and stirred at room temperature for 1 hour. Thereafter, a 25% aqueous ammonia solution (0.10 ml, excess amount) was added to the reaction system, and the mixture was stirred at room temperature for 3 hours. The reaction mixture was diluted with ethyl acetate and washed with saturated aqueous sodium hydrogen carbonate. The organic layer is simply purified by silica gel filtration using ethyl acetate, the solvent is concentrated under reduced pressure, and the resulting residue is washed with a mixed solvent of n-hexane-ethyl acetate to give the title compound. Got.
MS (APCI, m / z): 488 (M + H) ⁺ .
HPLC; Rt = 4.59min.

(Example 239)
4- [2- [N- (2,3-Dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetylamino]-(N-methyl) benzamide (compound of Exemplified Compound No. 1-612)
Reaction was carried out in the same manner as in Example 238 using 40% aqueous methylamine solution, and the title compound was obtained.
MS (APCI, m / z): 502 (M + H) ⁺ .
HPLC; Rt = 4.76min.

(Example 240)
4- [2- [N- (2,3-Dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetylamino]-(N, N-dimethyl) benzamide (compound of Exemplified Compound No. 1-615)
Reaction was carried out in the same manner as in Example 238 using 50% aqueous dimethylamine solution, and the title compound was obtained.
MS (APCI, m / z): 516 (M + H) ⁺ .
HPLC; Rt = 4.96min.

(Example 241)
N- [4- (1-butoxy) phenyl] -2- [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetamide (compound of exemplary compound number 1-559)
Similar to Example 152, using [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetic acid and 4- (1-butoxy) aniline prepared in Reference Example 1. To give the title compound.
MS (APCI, m / z): 517 (M + H) ⁺ .
HPLC; Rt = 6.97min.

(Example 242)
2- [N- (2,3-Dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- [4- (imidazol-1-yl) phenyl] acetamide (Compound of Exemplified Compound No. 1-793) )
Using [N- (2,3-dimethylphenyl) -N- (naphthalen-1-sulfonyl) amino] acetic acid prepared in Reference Example 1 and 4- (1H-imidazol-1-yl) aniline The reaction was conducted in the same manner as in Example 152 to obtain the title compound.
MS (APCI, m / z): 511 (M + H) ⁺ .
HPLC; Rt = 3.94min.

(Example 243)
2- [N- (2,3-Dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- [4- (morpholin-4-yl) phenyl] acetamide (Compound of Exemplified Compound No. 1-1031) )
Using [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetic acid and 4- (morpholin-4-yl) aniline prepared in Reference Example 1, Example 152 To give the title compound.
MS (APCI, m / z): 530 (M + H) ⁺ .
HPLC; Rt = 5.39min.

(Example 244)
N- (4-Dimethylaminophenyl) -2- [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetamide (compound of Exemplified Compound No. 1-583)
Using [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetic acid prepared in Reference Example 1 and N, N-dimethyl-1,4-phenylenediamine The reaction was conducted in the same manner as in Example 152 to obtain the title compound.
MS (APCI, m / z): 488 (M + H) ⁺ .
HPLC; Rt = 4.41min.

(Example 245)
N- (4-diethylaminophenyl) -2- [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetamide (compound of exemplary compound number 1-589)
Using [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetic acid prepared in Reference Example 1 and N, N-diethyl-1,4-phenylenediamine The reaction was conducted in the same manner as in Example 152 to obtain the title compound.
MS (APCI, m / z): 516 (M + H) ⁺ .
HPLC; Rt = 4.14min.

(Example 246)
N- (4-Benzoylphenyl) -2- [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetamide (compound of Exemplified Compound No. 1-1048)
The reaction was performed in the same manner as in Example 152 using [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetic acid and 4-aminobenzophenone prepared in Reference Example 1. The title compound was obtained.
MS (APCI, m / z): 549 (M + H) ⁺ .
HPLC; Rt = 6.49min.

(Example 247)
2- [N- (2,3-Dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- [4- (piperidin-1-yl) phenyl] acetamide (compound of Exemplified Compound No. 1-1019 )
Using [N- (2,3-dimethylphenyl) -N- (naphthalen-1-sulfonyl) amino] acetic acid and 4- (piperidin-1-yl) aniline prepared in Reference Example 1, Example 152 To give the title compound.
MS (APCI, m / z): 528 (M + H) ⁺ .
HPLC; Rt = 4.21min.

(Example 248)
2- [N- (2,3-Dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- (4-methylsulfamoylmethylphenyl) acetamide (compound of Exemplified Compound No. 1-37)
Using [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetic acid and 4-amino-N-methyl-α-toluenesulfonamide prepared in Reference Example 1, The reaction was conducted in the same manner as in Example 152 to obtain the title compound.
MS (APCI, m / z): 552 (M + H) ⁺ .
HPLC; Rt = 5.10min.

(Example 249)
2- [N- (2,3-Dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- [4- (1-hydroxyiminoethyl) phenyl] acetamide (Compound of Exemplified Compound No. 1-38 )
N- (4-acetylphenyl) -2- [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetamide (24 mg, 0.050 mmol) prepared in Example 169 was added to 1 , 4-dioxane-ethanol (2: 1, 1.5 ml), hydroxylamine hydrochloride (7.0 mg, 0.10 mmol) and sodium acetate (10 mg, 0.13 mmol) were added, and the mixture was stirred at 80 ° C. for 20 hours. . The reaction mixture was diluted with ethyl acetate and washed with saturated aqueous sodium hydrogen carbonate. The organic layer is simply purified by silica gel filtration using ethyl acetate, the solvent is concentrated under reduced pressure, and the resulting residue is washed with a mixed solvent of n-hexane / diisopropyl ether / ethyl acetate. The title compound was obtained.
MS (APCI, m / z): 502 (M + H) ⁺ .
HPLC; Rt = 5.36min.

(Example 250)
2- [N- (2,3-Dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- [4- (1-methoxyiminoethyl) phenyl] acetamide (Compound of Exemplified Compound No. 1-42 )
The title compound was obtained in the same manner as in Example 249 using o-methylhydroxylamine hydrochloride.
MS (APCI, m / z): 516 (M + H) ⁺ .
HPLC; Rt = 6.47min.

(Example 251)
2- [N- (2,3-Dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- [4- (1-hydroxyethyl) phenyl] acetamide (compound of Exemplified Compound No. 1-36)
N- (4-acetylphenyl) -2- [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetamide (20 mg, 0.041 mmol) prepared in Example 169 was added to tetrahydrofuran. -After dissolving in ethanol (1: 1, 1.0 ml), sodium borohydride (5.0 mg, 0.13 mmol) was added, and the mixture was stirred at 40 ° C for 2 hours. The reaction mixture was diluted with ethyl acetate and washed with 1N hydrochloric acid. The organic layer is simply purified by silica gel filtration using ethyl acetate, the solvent is concentrated under reduced pressure, and the resulting residue is washed with a mixed solvent of n-hexane / diisopropyl ether / ethyl acetate. The title compound was obtained.
MS (APCI, m / z): 489 (M + H) ⁺ .
HPLC; Rt = 5.09min.

(Example 252)
2- [N- (2,3-Dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- (4-ethoxyphenyl) propionamide (compound of Exemplified Compound No. 2-25)
Using naphthalene-1-sulfonic acid [N- (2,3-dimethylphenyl)] amide prepared in Reference Example 2 and 2-bromo-N- (4-ethoxyphenyl) propionamide prepared in Reference Example 18 In the same manner as in Example 181, the title compound was obtained.
MS (APCI, m / z): 503 (M + H) ⁺ .
HPLC; Rt = 6.44min.

(Example 253)
[4- [2- [N- (2,3-Dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetylamino] phenoxy] acetic acid tert-butyl ester (compound of Exemplified Compound No. 1-638)
[N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetic acid prepared in Reference Example 1 and the known compound (4-aminophenoxy) acetic acid (tert Using -butyl) ester, the reaction was carried out in the same manner as in Example 152 to obtain the title compound.
MS (APCI, m / z): 575 (M + H) ⁺ .
HPLC; Rt = 6.42min.

(Example 254)
2- [N- (2,3-Dimethylphenyl) -N- (2-nitrobenzenesulfonyl) amino] -N- (4-ethoxyphenyl) acetamide (compound of Exemplified Compound No. 1-249)
The title compound was obtained in the same manner as in Example 191 using 2-nitrobenzenesulfonyl chloride.
MS (APCI, m / z): 484 (M + H) ^<+> .
HPLC; Rt = 5.50min.

(Example 255)
N- (4-acetyl-3-hydroxyphenyl) -2- [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetamide (compound of exemplary compound number 1-688)
Using [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetic acid and 1- (4-amino-2-hydroxyphenyl) ethanone prepared in Reference Example 1, The reaction was conducted in the same manner as in Example 152 to obtain the title compound.
¹ H-NMR (DMSO-d ₆ ) δ: 12.22 (s, 1H), 10.27 (s, 1H), 8.28 (d like, 2H, J = 8.1Hz), 8.08 (d like, 2H, J = 7.3Hz ), 7.81 (d, 1H, J = 8.9Hz), 7.64 (d, 1H, J = 7.8Hz), 7.61 (d, 1H, J = 7.6Hz), 7.48 (dd, 1H, J = 8.4, 7.3Hz) ), 7.21 (d, 1H, J = 2.2Hz), 7.10 (dd, 1H, J = 4.9, 4.1Hz), 6.97-6.92 (m, 3H), 4.61 (d, 1H, J = 17.3Hz), 4.36 (d, 1H, J = 17.3Hz), 2.55 (s, 3H), 2.12 (s, 3H), 1.80 (s, 3H).
MS (APCI, m / z): 503 (M + H) ⁺ .
HPLC; Rt = 5.64min.

(Example 256)
[4- [2- [N- (2,3-Dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetylamino] phenoxy] acetic acid (compound of exemplified compound number 1-636)
[4- [2- [N- (2,3-Dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetylamino] phenoxy] acetic acid tert-butyl ester (323 mg, 0.562) prepared in Example 253 mmol) was dissolved in dichloromethane (2.0 ml) and cooled to 0 ° C., 50% trifluoroacetic acid (2.0 ml) was added in dichloromethane, and the mixture was stirred for 3 hours while slowly warming from 0 ° C. to room temperature. The reaction solution was diluted with dichloromethane and washed with 1N hydrochloric acid and saturated brine. The organic layer was dried over anhydrous sodium sulfate, the solvent was concentrated under reduced pressure, and the obtained residue was washed with a mixed solvent of n-hexane-diisopropyl ether to obtain the title compound (230 mg, 79%). .
MS (APCI, m / z): 519 (M + H) ⁺ .
HPLC; Rt = 4.68min.

(Example 257)
2- [4- [2- [N- (2,3-Dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetylamino] phenoxy] acetamide (compound of exemplary compound number 1-642)
[4- [2- [N- (2,3-Dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetylamino] phenoxy] acetic acid (20 mg, 0.039 mmol) prepared in Example 256 was dissolved in dichloromethane. After being dissolved in (1.0 ml), 1,1′-carbonylbis-1H-imidazole (9.4 mg, 0.058 mmol) was added and stirred at room temperature for 1 hour. Thereafter, a 25% aqueous ammonia solution (0.10 ml, excess amount) was added to the reaction system, and the mixture was stirred at room temperature for 2.5 hours. The reaction mixture was diluted with ethyl acetate and washed with saturated aqueous sodium hydrogen carbonate. The organic layer is simply purified by silica gel filtration using ethyl acetate, the solvent is concentrated under reduced pressure, and the resulting residue is washed with a mixed solvent of n-hexane-ethyl acetate to give the title compound. Got.
¹ H-NMR (DMSO-d ₆ ) δ: 9.83 (s, 1H), 8.30 (d, 1H, J = 7.3Hz), 8.27 (d, 1H, J = 7.0Hz), 8.09 (d like, 2H, J = 7.3Hz), 7.64 (d, 1H, J = 7.6Hz), 7.61 (d, 1H, J = 8.1Hz), 7.52-7.45 (m, 2H), 7.35 (d like, 3H, J = 9.2Hz ), 7.10 (dd, 1H, J = 5.4, 3.0Hz), 6.96-6.85 (m, 2H), 6.86 (d, 2H, J = 9.2Hz), 4.52 (d, 1H, J = 16.5Hz), 4.35 (s, 1H), 4.30 (d, 1H, J = 16.5Hz), 2.13 (s, 3H), 1.84 (s, 3H).
MS (APCI, m / z): 518 (M + H) ^<+> .
HPLC; Rt = 4.63 min.

(Example 258)
2- [N- (2,3-Dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- [4- (methylcarbamoylmethoxy) phenyl] acetamide (compound of Exemplified Compound No. 1-652)
Reaction was carried out in the same manner as in Example 257 using 40% aqueous methylamine solution, and the title compound was obtained.
MS (APCI, m / z): 532 (M + H) ⁺ .
HPLC; Rt = 4.83min.

(Example 259)
N- (4-Dimethylcarbamoylmethoxyphenyl) -2- [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetamide (compound of exemplary compound number 1-660)
Reaction was carried out in the same manner as in Example 257 using a 50% aqueous dimethylamine solution, and the title compound was obtained.
MS (APCI, m / z): 546 (M + H) ⁺ .
HPLC; Rt = 4.9 min.

(Example 260)
2- [N- (2,3-Dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- (4-methanesulfinylphenyl) acetamide (compound of exemplary compound number 1-575)
2- [N- (2,3-Dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- (4-methylsulfanylphenyl) acetamide (20 mg, 0.041 mmol) prepared in Example 233 was used. After dissolving in dichloromethane (1.0 ml), m-chloroperbenzoic acid (purity 65% or more, 11 mg, 0.041 mmol) was added and stirred at room temperature for 18 hours. The reaction solution was diluted with ethyl acetate and washed with a saturated aqueous sodium thiosulfate solution and a saturated aqueous sodium bicarbonate solution. The organic layer is simply purified by silica gel filtration using ethyl acetate, the solvent is concentrated under reduced pressure, and the resulting residue is washed with a mixed solvent of n-hexane / diisopropyl ether / ethyl acetate. The title compound was obtained.
MS (APCI, m / z): 507 (M + H) ⁺ .
HPLC; Rt = 4.71 min.

(Example 261)
2- [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- (4-methanesulfonylphenyl) acetamide (compound of exemplary compound number 1-576)
2- [N- (2,3-Dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- (4-methylsulfanylphenyl) acetamide (20 mg, 0.041 mmol) prepared in Example 233 was used. After dissolving in dichloromethane (1.0 ml), m-chloroperbenzoic acid (purity 65% or more, 501 mg, 0.20 mmol) was added and stirred at room temperature for 18 hours. The reaction solution was diluted with ethyl acetate and washed with a saturated aqueous sodium thiosulfate solution and a saturated aqueous sodium bicarbonate solution. The organic layer is simply purified by silica gel filtration using ethyl acetate, the solvent is concentrated under reduced pressure, and the resulting residue is washed with a mixed solvent of n-hexane / diisopropyl ether / ethyl acetate. The title compound was obtained.
MS (APCI, m / z): 523 (M + H) ⁺ .
HPLC; Rt = 5.22min.

(Example 262)
2- [N- (2,3-Dimethylphenyl) -N- [4- (pyrazol-1-yl) benzenesulfonyl] amino] -N- (4-ethoxyphenyl) acetamide (Compound No. 1-296) )
2- [N- (2,3-dimethylphenyl) amino] -N- (4-ethoxyphenyl) acetamide monohydrochloride prepared in Reference Example 6 was dissolved in pyridine (1.0 ml) and 4- (1H-pyrazole was dissolved. 1-yl) benzenesulfonyl chloride (24 mg, 0.10 mmol) was added and stirred at 70 ° C. for 16 hours. The reaction mixture was diluted with ethyl acetate and washed with saturated aqueous sodium hydrogen carbonate. The organic layer is simply purified by silica gel filtration using ethyl acetate, the solvent is concentrated under reduced pressure, and the resulting residue is washed with a mixed solvent of n-hexane / diisopropyl ether / ethyl acetate. The title compound was obtained.
MS (APCI, m / z): 505 (M + H) ⁺ .
HPLC; Rt = 5.58min.

(Example 263)
2- [N- (2,3-Dimethyl-phenyl) -N- [4- (oxazol-5-yl) benzenesulfonyl] amino] -N- (4-ethoxyphenyl) acetamide (Exemplary Compound No. 1-298 Compound)
The title compound was obtained in the same manner as in Example 262, using 4- (oxazol-5-yl) benzenesulfonyl chloride.
MS (APCI, m / z): 506 (M + H) ⁺ .
HPLC; Rt = 5.22min.

(Example 264)
2- [N- (2,3-Dimethylphenyl) -N- [3- (5-methyl- [1,3,4] oxadiazol-2-yl) benzenesulfonyl] amino] -N- (4- Ethoxyphenyl) acetamide (Compound No. 1-301)
The title compound was obtained in the same manner as in Example 262, using 3- (5-methyl- [1,3,4] oxadiazol-2-yl) benzenesulfonyl chloride.
MS (APCI, m / z): 521 (M + H) ⁺ .
HPLC; Rt = 5.04min.

(Example 265)
2- [N- (2,3-dimethylphenyl) -N- [5- (pyridin-2-yl) thiophene-2-sulfonyl] amino] -N- (4-ethoxyphenyl) acetamide (Exemplary Compound No. 1- 321 compounds)
The title compound was obtained by reacting in the same manner as in Example 262 using 5- (pyridin-2-yl) thiophene-2-sulfonyl chloride.
MS (APCI, m / z): 522 (M + H) ⁺ .
HPLC; Rt = 5.79min.

(Example 266)
2- [N- (2,3-Dimethylphenyl) -N- [6- (morpholin-4-yl) pyridine-3-sulfonyl] amino] -N- (4-ethoxyphenyl) acetamide (Exemplary Compound No. 1- 334 compounds)
The title compound was obtained in the same manner as in Example 262, using 6- (morpholin-4-yl) pyridine-3-sulfonyl chloride.
MS (APCI, m / z): 525 (M + H) ⁺ .
HPLC; Rt = 5.19min.

(Example 267)
2- [N- (2,3-dimethylphenyl) -N- [3- (4-fluorophenyl) phenylsulfonyl] amino] -N- (4-ethoxyphenyl) acetamide (compound of exemplary compound number 1-293)
The title compound was obtained in the same manner as in Example 262, using 3- (4-fluorophenyl) phenylsulfonyl chloride.
MS (APCI, m / z): 533 (M + H) ⁺ .
HPLC; Rt = 6.54min.

(Example 268)
2- [N- (2,3-Dimethylphenyl) -N- [4- (4-fluorophenyl) phenylsulfonyl] amino] -N- (4-ethoxyphenyl) acetamide (compound of exemplary compound number 1-294)
The title compound was obtained in the same manner as in Example 262, using 4- (4-fluorophenyl) phenylsulfonyl chloride.
MS (APCI, m / z): 533 (M + H) ⁺ .
HPLC; Rt = 6.54min.

(Example 269)
2- [N- [3- (4-Chlorophenyl) phenylsulfonyl] -N- (2,3-dimethylphenyl) amino] -N- (4-ethoxyphenyl) acetamide (Compound No. 1-295)
The title compound was obtained in the same manner as in Example 262, using 3- (4-chlorophenyl) phenylsulfonyl chloride.
MS (APCI, m / z): 549 (M + H) ⁺ , 551 (M + H) ⁺ .
HPLC; Rt = 7.01 min.

(Example 270)
2- [N- (2,3-dimethylphenyl) -N- [5- (2-methylsulfanylpyrimidin-4-yl) thiophen-2-sulfonyl] amino] -N- (4-ethoxyphenyl) acetamide (illustrated Compound No. 1-325)
The title compound was obtained in the same manner as in Example 262, using 5- (2-methylsulfanylpyrimidin-4-yl) thiophene-2-sulfonyl chloride.
MS (APCI, m / z): 569 (M + H) ⁺ .
HPLC; Rt = 6.14min.

(Example 271)
2- [N- (2,3-Dimethylphenyl) -N- [5- (5-trifluoromethylisoxazol-3-yl) thiophene-2-sulfonyl] amino] -N- (4-ethoxyphenyl) Acetamide (Exemplary Compound No. 1-328 Compound)
The title compound was obtained in the same manner as in Example 262, using 5- (5-trifluoromethylisoxazol-3-yl) thiophene-2-sulfonyl chloride.
MS (APCI, m / z): 580 (M + H) ⁺ .
HPLC; Rt = 6.59min.

(Example 272)
2- [N- (2,3-dimethylphenyl) -N- [3- (4-trifluoromethylphenyl) phenylsulfonyl] amino] -N- (4-ethoxyphenyl) acetamide (Exemplary Compound No. 1-291 Compound)
The title compound was obtained in the same manner as in Example 262, using 3- (4-trifluoromethylphenyl) phenylsulfonyl chloride.
MS (APCI, m / z): 583 (M + H) ⁺ .
HPLC; Rt = 6.98 min.

(Example 273)
2- [N- (2,3-dimethylphenyl) -N- [4- (4-trifluoromethylphenyl) phenylsulfonyl] amino] -N- (4-ethoxyphenyl) acetamide (Exemplary Compound No. 1-292 Compound)
Using 4- (4-trifluoromethylphenyl) phenylsulfonyl chloride, the reaction was carried out in the same manner as in Example 262 to obtain the title compound.
MS (APCI, m / z): 583 (M + H) ^<+> .
HPLC; Rt = 6.94min.

(Example 274)
3- [5- [N- (2,3-Dimethylphenyl) -N-[[N- (4-ethoxyphenyl) carbamoyl] methyl] sulfamoyl] thiophen-2-yl]-[1,2,4] oxa Diazole-5-carboxylic acid ethyl ester (compound of Exemplified Compound No. 1-332)
The title compound was obtained in the same manner as in Example 262 using 3- [5- (chlorosulfonyl) -2-thienyl] -1,2,4-oxadiazole-5-carboxylic acid ethyl ester. .
MS (APCI, m / z): 585 (M + H) ⁺ .
HPLC; Rt = 6.03min.

(Example 275)
2- [N- (2,3-Dimethylphenyl) -N- [5- (2-methyl-5-trifluoromethyl-2H-pyrazol-3-yl) thiophen-2-sulfonyl] amino] -N- ( 4-Ethoxyphenyl) acetamide (compound of Exemplified Compound No. 1-323)
The title compound was obtained in the same manner as in Example 262, using 5- (2-methyl-5-trifluoromethyl-2H-pyrazol-3-yl) thiophene-2-sulfonyl chloride.
MS (APCI, m / z): 593 (M + H) ⁺ .
HPLC; Rt = 6.44min.

(Example 276)
2- [N- (2,3-Dimethylphenyl) -N- [3- (2-methylpyrimidin-4-yl) benzenesulfonyl] amino] -N- (4-ethoxyphenyl) acetamide (Exemplary Compound No. 1- 303 compounds)
The title compound was obtained in the same manner as in Example 262, using 3- (2-methylpyrimidin-4-yl) benzenesulfonyl chloride.
MS (APCI, m / z): 531 (M + H) ^<+> .
HPLC; Rt = 5.36min.

(Example 277)
N- (4-Ethoxyphenyl) -2- [N- (2-methylpyridin-3-yl) -N- (naphthalene-1-sulfonyl) amino] acetamide (compound of Exemplified Compound No. 1-439)
The reaction was carried out in the same manner as in Example 227 using (2-methylpyridin-3-yl) amine to obtain the title compound.
MS (APCI, m / z): 476 (M + H) ⁺ .
HPLC; Rt = 4.38min.

(Example 278)
N- (4-Ethoxyphenyl) -2- [N- (5-methylpyridin-3-yl) -N- (naphthalene-1-sulfonyl) amino] acetamide (compound of Exemplified Compound No. 1-440)
The reaction was carried out in the same manner as in Example 227 using (5-methylpyridin-3-yl) amine to obtain the title compound.
MS (APCI, m / z): 476 (M + H) ⁺ .
HPLC; Rt = 3.74min.

(Example 279)
N- (4-Ethoxyphenyl) -2- [N- (6-methylpyridin-3-yl) -N- (naphthalene-1-sulfonyl) amino] acetamide (compound of exemplary compound number 1-441)
The reaction was carried out in the same manner as in Example 227 using (6-methylpyridin-3-yl) amine to obtain the title compound.
MS (APCI, m / z): 476 (M + H) ⁺ .
HPLC; Rt = 4.5 min.

(Example 280)
2- [N- (2,3-Dimethylphenyl) -N- (quinoline-8-sulfonyl) amino] -N- (4-ethoxyphenyl) acetamide (Compound of Exemplified Compound No. 1-333)
Using the quinoline-8-sulfonic acid [N- (2,3-dimethylphenyl)] amide prepared in Reference Example 12 and 2-bromo-N- (4-ethoxyphenyl) acetamide prepared in Reference Example 7 The reaction was conducted in the same manner as in Example 181 to obtain the title compound.
MS (APCI, m / z): 490 (M + H) ⁺ .
HPLC; Rt = 5.24min.

(Example 281)
2- [N- (2,3-Dimethylphenyl) -N- [5- (oxazol-5-yl) thiophene-2-sulfonyl] amino] -N- (4-ethoxyphenyl) acetamide (Exemplary Compound No. 1- 326 compounds)
The title compound was obtained in the same manner as in Example 262, using 5- (oxazol-5-yl) thiophene-2-sulfonyl chloride.
MS (APCI, m / z): 512 (M + H) ⁺ .
HPLC; Rt = 5.28min.

(Example 282)
2- [N- (2,3-Dimethylphenyl) -N- [5- (isoxazol-3-yl) thiophen-2-sulfonyl] amino] -N- (4-ethoxyphenyl) acetamide (Exemplary Compound No. 1- 327 compounds)
The title compound was obtained in the same manner as in Example 262 using 5- (isoxazol-3-yl) thiophene-2-sulfonyl chloride.
MS (APCI, m / z): 512 (M + H) ⁺ .
HPLC; Rt = 5.56min.

(Example 283)
N- (4-Cyanophenyl) -2- [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetamide (compound of exemplary compound number 1-621)
Using [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetic acid and 4-aminobenzonitrile prepared in Reference Example 1, the reaction was conducted in the same manner as in Example 152. And the title compound was obtained.
MS (APCI, m / z): 470 (M + H) ⁺ .
HPLC; Rt = 5.78min.

(Example 284)
2- [N- (2,3-Dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- [4- (1H-tetrazol-5-yl) phenyl] acetamide (Exemplary Compound No. 1-1016 Compound)
N- (4-cyanophenyl) -2- [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetamide (50 mg, 0.11 mmol) prepared in Example 283 was replaced with N , N-dimethylformamide (1.0 ml), sodium azide (69 mg, 1.06 mmol) and ammonium chloride (57 mg, 1.06 mmol) were added, and the mixture was stirred at 120 ° C. for 16 hours. The reaction mixture was diluted with ethyl acetate and washed with 1N hydrochloric acid, water and saturated brine. The organic layer was dried over anhydrous sodium sulfate, the solvent was concentrated under reduced pressure, and the obtained residue was washed with a mixed solvent of n-hexane / diisopropyl ether / ethyl acetate to obtain the title compound.
MS (APCI, m / z): 513 (M + H) ⁺ .
HPLC; Rt = 4.74min.

(Example 285)
N- (4-acetyl-3-hydroxyphenyl) -2- [N- (2-methoxypyridin-3-yl) -N- (quinoline-8-sulfonyl) amino] acetamide (compound of Exemplified Compound No. 1-691) )
Using [N- (2-methoxypyridin-3-yl) -N- (quinolin-8-sulfonyl) amino] acetic acid and 1- (4-amino-2-hydroxyphenyl) ethanone prepared in Reference Example 13 In the same manner as in Example 152, the title compound was obtained.
MS (APCI, m / z): 507 (M + H) ⁺ .
HPLC; Rt = 4.53min.

(Example 286)
N- [4- (imidazol-1-yl) phenyl] -2- [N- (2-methoxypyridin-3-yl) -N- (quinolin-8-sulfonyl) amino] acetamide (Exemplified Compound No. 1-848 Compound)
Using [N- (2-methoxypyridin-3-yl) -N- (quinolin-8-sulfonyl) amino] acetic acid and 4- (1H-imidazol-1-yl) aniline prepared in Reference Example 13 In the same manner as in Example 152, the title compound was obtained.
¹ H-NMR (DMSO-d ₆ ) δ: 10.19 (s, 1H), 9.09 (dd, 1H, J = 4.3, 1.6Hz), 8.58 (dd, 1H, J = 8.4, 1.6Hz), 8.29 (dd , 1H, J = 8.4, 1.4Hz), 8.17 (dd, 1H, J = 1.4, 0.8Hz), 8.10 (dd, 1H, J = 7.3, 1.4Hz), 8.02 (dd, 1H, J = 4.9, 1.9 Hz), 7.89 (dd, 1H, J = 7.6, 1.9Hz), 7.74 (dd, 1H, J = 8.4, 4.3Hz), 7.70-7.60 (m, 2H), 7.66 (d, 2H, J = 9.2Hz ), 7.57 (d, 2H, J = 9.2Hz), 7.08 (dd, 1H, J = 1.4, 0.8Hz), 7.01 (dd, 1H, J = 7.6, 4.9), 4.94 (s, 2H), 2.92 ( s, 3H).
MS (APCI, m / z): 515 (M + H) ⁺ .
HPLC; Rt = 3.13min.

(Example 287)
[4- [2- [N- (2-methoxypyridin-3-yl) -N- (quinolin-8-sulfonyl) amino] acetylamino] phenoxy] acetic acid tert-butyl ester (compounds of Exemplified Compound Nos. 1-639) )
[N- (2-methoxypyridin-3-yl) -N- (quinolin-8-sulfonyl) amino] acetic acid prepared in Reference Example 13 and the known compound (4-aminophenoxy) acetic acid shown in Reference Example 15 The reaction was carried out in the same manner as in Example 152 using (tert-butyl) ester to obtain the title compound.
MS (APCI, m / z): 579 (M + H) ⁺ .
HPLC; Rt = 5.05min.

(Example 288)
2- [4- [2- [N- (2-methoxypyridin-3-yl) -N- (quinolin-8-sulfonyl) amino] acetylamino] phenoxy] acetamide (compound of exemplary compound number 1-647), and,

Example 289
2- [4- [2- [N- (2-oxo-1,2-dihydropyridin-3-yl) -N- (quinoline-8-sulfonyl) amino] acetylamino] phenoxy] acetamide (Exemplary Compound No. 1- 648 compounds)
[4- [2- [N- (2-Methoxypyridin-3-yl) -N- (quinolin-8-sulfonyl) amino] acetylamino] phenoxy] acetic acid tert-butyl ester (60 mg) prepared in Example 287 , 0.10 mmol) was dissolved in dichloromethane (1.0 ml) and cooled to 0 ° C., 50% trifluoroacetic acid (1.0 ml) was added in dichloromethane, and the mixture was stirred for 3 hours while slowly warming from 0 ° C. to room temperature. . The reaction mixture was concentrated under reduced pressure, the obtained residue was dissolved in 1,4-dioxane (2.0 ml), 4N hydrochloric acid-dioxane solution (0.5 ml) was added, and the mixture was stirred at room temperature for 10 min. N-Hexane was added to the reaction solution to suspend it, and the precipitated solid was collected by filtration and dried under reduced pressure.
The obtained solid was dissolved in N, N-dimethylformamide (1.0 ml), 1-hydroxy-7-azabenzotriazole (11.6 mg, 0.085 mmol) was added, and the mixture was stirred at room temperature for 5 minutes. Subsequently, ammonia-dioxane (0.5 M; 0.57 ml, 0.28 mmol) and a1-ethyl-3- (dimethylaminopropyl) carbodiimide hydrochloride (22 mg, 0.11 mmol) were added, and the mixture was stirred at 40 ° C. for 5 hours. The reaction mixture was diluted with ethyl acetate and washed with saturated aqueous sodium hydrogen carbonate and saturated brine. The organic layer was dried over anhydrous sodium sulfate, the solvent was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (elution solvent: dichloromethane / methanol = 10/1). Compound 2- [4- [2- [N- (2-methoxypyridin-3-yl) -N- (quinolin-8-sulfonyl) amino] acetylamino] phenoxy] acetamide and compound 2- of Example 289 [4- [2- [N- (2-oxo-1,2-dihydropyridin-3-yl) -N- (quinoline-8-sulfonyl) amino] acetylamino] phenoxy] acetamide was obtained.
(Compound of Example 288)
MS (APCI, m / z): 522 (M + H) ⁺ .
HPLC; Rt = 3.52min.
(Compound of Example 289)
MS (APCI, m / z): 508 (M + H) ⁺ .
HPLC; Rt = 2.89min.

(Example 290)
2- [N- (2,3-Dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- [4- (imidazol-1-yl) phenyl] acetamide hydrochloride (Exemplified Compound No. 1-793 Hydrochloride of the compound)
2- [N- (2,3-Dimethylphenyl) -N- (naphthalen-1-sulfonyl) amino] -N- [4- (imidazol-1-yl) phenyl] acetamide (15 mg) prepared in Example 242 , 0.029 mmol) was dissolved in 1,4-dioxane (1.0 ml), 4N hydrochloric acid-dioxane solution (0.022 ml, 0.088 mmol) was added, and the mixture was stirred at room temperature for 10 minutes. The reaction mixture was concentrated under reduced pressure, and the obtained residue was washed with a mixed solvent of ethanol-diethyl ether to obtain the title compound.
¹ H-NMR (DMSO-d ₆ ) δ: 10.45 (s, 1H), 9.60 (br s, 1H), 8.29 (d like, 2H, J = 8.4 Hz), 8.21 (dd, 1H, J = 1.9, 1.6Hz), 8.10 (d like, 2H, J = 7.6Hz), 7.88 (dd, 1H, J = 1.6, 1.6Hz), 7.71 (br s, 4H), 7.65 (d, 1H, J = 7.8Hz) , 7.62 (d, 1H, J = 7.6Hz), 7.49 (dd like, 1H, J = 8.4, 7.0Hz), 7.11 (dd, 1H, J = 6.5, 2.2Hz), 7.00-6.90 (m, 2H) , 4.64 (d, 1H, J = 16.7Hz), 4.39 (d, 1H, J = 16.7Hz), 2.12 (s, 3H), 1.80 (s, 3H).
MS (APCI, m / z): 511 (M + H) ⁺ .
HPLC; Rt = 3.85min.

(Example 291)
2- [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- [3-hydroxy-4- (1-hydroxyiminoethyl) phenyl] acetamide (Exemplary Compound No. 1 -683 compounds)
N- (4-acetyl-3-hydroxyphenyl) -2- [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetamide and hydroxylamine hydrochloride prepared in Example 255 Was used in the same manner as in Example 249 to give the title compound.
MS (APCI, m / z): 518 (M + H) ^<+> .
HPLC; Rt = 5.24min.

(Example 292)
2- [N- (2,3-Dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- [3-hydroxy-4- (1-methoxyiminoethyl) phenyl] acetamide (Exemplary Compound No. 1 -687 compounds)
N- (4-acetyl-3-hydroxyphenyl) -2- [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetamide and o-methylhydroxyl prepared in Example 255 Using the amine hydrochloride, the reaction was carried out in the same manner as in Example 249 to obtain the title compound.
MS (APCI, m / z): 532 (M + H) ⁺ .
HPLC; Rt = 6.13min.

(Example 293)
2- [N- (2,3-Dimethylphenyl) -N- (isoquinoline-5-sulfonyl) amino] -N- (4-ethoxyphenyl) acetamide (compound of Exemplified Compound No. 1-351)
Reaction was carried out in the same manner as in Example 262 using isoquinoline-5-sulfonyl chloride to obtain the title compound.
MS (APCI, m / z): 490 (M + H) ⁺ .
HPLC; Rt = 4.75min.

(Example 294)
2- [N- (2,3-Dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- (4-hydroxyphenyl) acetamide (compound of Exemplified Compound No. 1-46)
The reaction was conducted in the same manner as in Example 152 using [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetic acid and 4-aminophenol prepared in Reference Example 1. The title compound was obtained.
¹ H-NMR (DMSO-d ₆ ) δ: 10.15 (s, 1H), 9.17 (dd, 1H, J = 4.3, 1.6Hz), 8.60 (dd, 1H, J = 8.1, 1.9Hz), 8.31 (dd , 1H, J = 8.4, 1.4Hz), 8.17 (br s, 1H), 8.09 (dd, 1H, J = 7.3, 1.6Hz), 7.77 (dd, 1H, J = 8.1, 4.3Hz), 7.69-7.60 (m, 4H), 7.56 (d, 1H, J = 8.9Hz), 7.08 (br s, 1H), 7.05-7.01 (m, 1H), 6.89-6.86 (m, 2H), 5.18 (d, 1H, J = 17.1Hz), 4.81 (d, 1H, J = 17.1Hz), 2.11 (s, 3H), 1.83 (s, 3H).
MS (APCI, m / z): 461 (M + H) ⁺ .
HPLC; Rt = 4.78min.

(Example 295)
2- [N- (2,3-Dimethylphenyl) -N- (quinolin-8-sulfonyl) amino] -N- [4- (imidazol-1-yl) phenyl] acetamide (Compound of Exemplified Compound No. 1-808) )
Using [N- (2,3-dimethylphenyl) -N- (quinolin-8-sulfonyl) amino] acetic acid prepared in Reference Example 11 and 4- (1H-imidazol-1-yl) aniline The reaction was conducted in the same manner as in Example 152 to obtain the title compound.
MS (APCI, m / z): 512 (M + H) ⁺ .
HPLC; Rt = 3.62min.

(Example 296)
N- (4-Dimethylamino-phenyl) -2-[(2,3-dimethyl-phenyl)-(quinoline-8-sulfonyl) -amino] -acetamide (compound of Exemplified Compound No. 1-584)
Using [N- (2,3-dimethylphenyl) -N- (quinoline-8-sulfonyl) amino] acetic acid prepared in Reference Example 11 and N, N-dimethyl-1,4-phenylenediamine, Examples The reaction was conducted in the same manner as in 152 to give the title compound.
MS (APCI, m / z): 489 (M + H) ⁺ .
HPLC; Rt = 3.87min.

(Example 297)
2- [N- (2,3-Dimethylphenyl) -N- (quinolin-8-sulfonyl) amino] -N- [4- (piperidin-1-yl) phenyl] acetamide (Exemplified Compound No. 1-1020) )
Similar to Example 152, using [N- (2,3-dimethylphenyl) -N- (quinoline-8-sulfonyl) amino] acetic acid and 4- (1-piperidino) aniline prepared in Reference Example 11. To give the title compound.
MS (APCI, m / z): 529 (M + H) ⁺ .
HPLC; Rt = 3.82min.

(Example 298)
2- [N- (2,3-Dimethylphenyl) -N- (quinoline-8-sulfonyl) amino] -N- (6-methoxypyridin-3-yl) acetamide (compound of Exemplified Compound No. 1-1098)
Using [N- (2,3-dimethylphenyl) -N- (quinolin-8-sulfonyl) amino] acetic acid and (6-methoxypyridin-3-yl) amine prepared in Reference Example 11, Example 152 and Reaction was performed in the same manner to obtain the title compound.
MS (APCI, m / z): 477 (M + H) ⁺ .
HPLC; Rt = 4.74min.

(Example 299)
N- (6-chloropyridin-3-yl) -2- [N- (2,3-dimethylphenyl) -N- (quinoline-8-sulfonyl) amino] acetamide (compound of Exemplified Compound No. 1-1102)
Using [N- (2,3-dimethylphenyl) -N- (quinolin-8-sulfonyl) amino] acetic acid and (6-chloropyridin-3-yl) amine prepared in Reference Example 11, The reaction was conducted in the same manner as in 152 to give the title compound.
MS (APCI, m / z): 481 (M + H) ⁺ , 483 (M + H) ⁺ .
HPLC; Rt = 5.02 min.

(Example 300)
2- [N- (2,3-Dimethylphenyl) -N- (quinoline-8-sulfonyl) amino] -N- (6-methylpyridin-3-yl) acetamide (compound of Exemplified Compound No. 1-1094)
Using [N- (2,3-dimethylphenyl) -N- (quinolin-8-sulfonyl) amino] acetic acid and (6-methylpyridin-3-yl) amine prepared in Reference Example 11, The reaction was conducted in the same manner as in 152 to give the title compound.
MS (APCI, m / z): 461 (M + H) ⁺ .
HPLC; Rt = 3.56min.

(Example 301)
N- (4-acetylphenyl) -2- [N- (2,3-dimethylphenyl) -N- (quinoline-8-sulfonyl) amino] acetamide (compound of exemplary compound number 1-600)
The reaction was performed in the same manner as in Example 152 using [N- (2,3-dimethylphenyl) -N- (quinoline-8-sulfonyl) amino] acetic acid and 4-aminoacetophenone prepared in Reference Example 11. The title compound was obtained.
MS (APCI, m / z): 488 (M + H) ⁺ .
HPLC; Rt = 4.92min.

(Example 302)
N- (4-acetyl-3-hydroxyphenyl) -2- [N- (2,3-dimethylphenyl) -N- (quinoline-8-sulfonyl) amino] acetamide (compound of Exemplified Compound No. 1-689)
Using [N- (2,3-dimethylphenyl) -N- (quinoline-8-sulfonyl) amino] acetic acid and 1- (4-amino-2-hydroxyphenyl) ethanone prepared in Reference Example 11, The reaction was conducted in the same manner as in Example 152 to obtain the title compound.
MS (APCI, m / z): 504 (M + H) ⁺ .
HPLC; Rt = 5.22min.

Example 303
2- [N- (2,3-dimethylphenyl) -N- (4-fluoronaphthalene-1-sulfonyl) amino] -N- (4-ethoxyphenyl) acetamide (compound of Exemplified Compound No. 1-314)
The title compound was obtained in the same manner as in Example 262 using 4-fluoronaphthalene-1-sulfonyl chloride.
MS (APCI, m / z): 507 (M + H) ⁺ .
HPLC; Rt = 6.43min.

(Example 304)
N- (4-acetylphenyl) -2- [N- (2-methoxypyridin-3-yl) -N- (quinoline-8-sulfonyl) amino] acetamide (compound of exemplary compound number 1-604)
Using [N- (2-methoxypyridin-3-yl) -N- (quinolin-8-sulfonyl) amino] acetic acid and 4-aminoacetophenone prepared in Reference Example 13, the reaction was carried out in the same manner as in Example 152. To obtain the title compound.
MS (APCI, m / z): 491 (M + H) ⁺ .
HPLC; Rt = 4.26min.

(Example 305)
N- (6-methoxypyridin-3-yl) -2- [N- (2-methoxypyridin-3-yl) -N- (quinoline-8-sulfonyl) amino] acetamide (Compound of Exemplified Compound No. 1-1100) )
Using [N- (2-methoxypyridin-3-yl) -N- (quinolin-8-sulfonyl) amino] acetic acid and (6-methoxypyridin-3-yl) amine prepared in Reference Example 13, The reaction was conducted in the same manner as in Example 152 to obtain the title compound.
MS (APCI, m / z): 480 (M + H) +.
HPLC; Rt = 3.95 min.

(Example 306)
N- (6-Chloropyridin-3-yl) -2- [N- (2-methoxypyridin-3-yl) -N- (quinolin-8-sulfonyl) amino] acetamide (Compound of Exemplified Compound No. 1-1104) )
Using [N- (2-methoxypyridin-3-yl) -N- (quinolin-8-sulfonyl) amino] acetic acid and 6-chloropyridin-3-ylamine prepared in Reference Example 13, Example 152 To give the title compound.
MS (APCI, m / z): 484 (M + H) ⁺ , 486 (M + H) ⁺ .
HPLC; Rt = 4.22min.

(Example 307)
2- [N- (2-methoxypyridin-3-yl) -N- (quinolin-8-sulfonyl) amino] -N- (6-methylpyridin-3-yl) acetamide (Compound of Exemplified Compound No. 1-1096) )
Using [N- (2-methoxypyridin-3-yl) -N- (quinolin-8-sulfonyl) amino] acetic acid and (6-methylpyridin-3-yl) amine prepared in Reference Example 13, The reaction was conducted in the same manner as in Example 152 to obtain the title compound.
MS (APCI, m / z): 464 (M + H) +.
HPLC; Rt = 2.94min.

(Example 308)
N- (4-Dimethylaminophenyl) -2- [N- (2-methoxypyridin-3-yl) -N- (quinoline-8-sulfonyl) amino] acetamide (compound of exemplary compound number 1-588)
Using [N- (2-methoxypyridin-3-yl) -N- (quinolin-8-sulfonyl) amino] acetic acid prepared in Reference Example 13 and N, N-dimethyl-1,4-phenylenediamine In the same manner as in Example 152, the title compound was obtained.
MS (APCI, m / z): 492 (M + H) ⁺ .
HPLC; Rt = 3.30min.

(Example 309)
2- [N- (2-methoxypyridin-3-yl) -N- (quinolin-8-sulfonyl) amino] -N- (4-piperidin-1-ylphenyl) acetamide (compound of Exemplified Compound No. 1-1022) )
Using [N- (2-methoxypyridin-3-yl) -N- (quinolin-8-sulfonyl) amino] acetic acid and 4- (1-piperidino) aniline prepared in Reference Example 13, Example 152 To give the title compound.
MS (APCI, m / z): 532 (M + H) ⁺ .
HPLC; Rt = 3.28min.

(Example 310)
2- [N- (2,3-Dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- (indan-1-yl) acetamide (compound of Exemplified Compound No. 1-1053)
The reaction was carried out in the same manner as in Example 152 using [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetic acid and 1-aminoindane prepared in Reference Example 1. The title compound was obtained.
MS (APCI, m / z): 485 (M + H) ⁺ .
HPLC; Rt = 6.23min.

(Example 311)
2- [N- (2,3-dimethylphenyl) -N = (naphthalene-1-sulfonyl) amino] -N- (3-phenoxybenzyl) acetamide (compound of Exemplified Compound No. 1-10)
Similar to Example 152, using [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetic acid and 3-phenoxybenzylamine hydrochloride prepared in Reference Example 1. Reaction was performed to obtain the title compound.
MS (APCI, m / z): 551 (M + H) ⁺ .
HPLC; Rt = 6.68min.

(Example 312)
N- (4-Ethoxyphenyl) -2- [N- (indan-1-yl) -N- (naphthalene-1-sulfonyl) amino] acetamide (Compound of Exemplified Compound No. 1-407)
The reaction was carried out in the same manner as in Example 227 using 1-aminoindan to obtain the title compound.
MS (APCI, m / z): 499 (MH) ⁺ .
HPLC; Rt = 6.26min.

(Example 313)
2- [N- (2-chlorobenzyl) -N- (naphthalene-1-sulfonyl) amino] -N- (4-ethoxyphenyl) acetamide (compound of exemplary compound number 1-87)
The reaction was carried out in the same manner as in Example 227 using 2-chlorobenzylamine to obtain the title compound.
MS (APCI, m / z): 509 (M + H) ⁺ , 511 (M + H) ⁺ .
HPLC; Rt = 6.21min.

(Example 314)
N- (4-Ethoxyphenyl) -2- [N- (naphthalene-1-sulfonyl) -N- (1-phenylethyl) amino] acetamide (compound of exemplary compound number 1-91)
The reaction was carried out in the same manner as in Example 227 using L-(−)-α-phenylethylamine to obtain the title compound.
MS (APCI, m / z): 487 (MH) ⁺ .
HPLC; Rt = 6.08min.

(Example 315)
2- [4- [2- [N- (2,3-Dimethylphenyl) -N- (quinoline-8-sulfonyl) amino] acetylamino] phenoxy] acetamide (compound of Exemplified Compound No. 1-643)
Using [4- [2- [N- (2,3-dimethylphenyl) -N- (quinoline-8-sulfonyl) amino] acetylamino] phenoxy] acetic acid prepared in Reference Example 19 and 25% aqueous ammonia solution The reaction was conducted in the same manner as in Example 257 to obtain the title compound.
MS (APCI, m / z): 519 (M + H) ⁺ .
HPLC; Rt = 4.08min.

(Example 316)
2- [N- (2,3-Dimethylphenyl) -N- (quinolin-8-sulfonyl) amino] -N- [4- (imidazol-1-yl) phenyl] acetamide dihydrochloride (Exemplary Compound No. 1- Dihydrochloride of 808 compounds)
Using 2- [N- (2,3-dimethylphenyl) -N- (quinolin-8-sulfonyl) amino] -N- [4- (imidazol-1-yl) phenyl] acetamide prepared in Example 295 In the same manner as in Example 290, the title compound was obtained.
¹ H-NMR (DMSO-d ₆ ) δ: 10.49 (s, 1H), 9.66 (br s, 1H), 9.20 (d, 1H, J = 4.1 Hz), 8.61 (d, 1H, J = 8.1 Hz) , 8.31 (d, 1H, J = 7.8Hz), 8.24 (br s, 1H), 8.09 (d, 1H, J = 7.3Hz), 7.92 (br s, 1H), 7.82-7.69 (m, 5H), 7.65 (dd, 1H, J = 8.4, 7.3Hz), 7.08-6.99 (m, 1H), 6.92-6.84 (m, 2H), 5.25 (d, 1H, J = 17.0Hz), 4.86 (d, 1H, J = 17.0Hz), 2.10 (s, 3H), 1.82 (s, 3H).
MS (APCI, m / z): 512 (M + H) ⁺ .
HPLC; Rt = 3.61min.

(Example 317)
2- [N- (2,3-Dimethylphenyl) -N- (quinoline-8-sulfonyl) amino] -N- [4- (N-methylcarbamoyl) methoxyphenyl] acetamide (Exemplary Compound No. 1-653 Compound )
[4- [2- [N- (2,3-dimethylphenyl) -N- (quinoline-8-sulfonyl) amino] acetylamino] phenoxy] acetic acid prepared in Reference Example 19 and a 40% aqueous methylamine solution were used. And the reaction was carried out in the same manner as in Example 257 to obtain the title compound.
MS (APCI, m / z): 533 (M + H) ⁺ .
HPLC; Rt = 4.22min.

(Example 318)
N- [4- (N, N-dimethylcarbamoyl) methoxyphenyl] -2- [N- (2,3-dimethylphenyl) -N- (quinoline-8-sulfonyl) amino] acetamide (Exemplified Compound No. 1-661 Compound)
[4- [2- [N- (2,3-dimethylphenyl) -N- (quinoline-8-sulfonyl) amino] acetylamino] phenoxy] acetic acid prepared in Reference Example 19 and 50% aqueous dimethylamine solution were used. In the same manner as in Example 257, the title compound was obtained.
MS (APCI, m / z): 547 (M + H) ⁺ .
HPLC; Rt = 4.28min.

(Example 319)
N- (5-chlorothiazol-2-yl) -2- [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetamide (compound of Exemplified Compound No. 1-1072)
Using [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetic acid and 2-amino-5-chlorothiazole hydrochloride prepared in Reference Example 1, Example 152 To give the title compound.
MS (APCI, m / z): 486 (M + H) ⁺ , 488 (M + H) ⁺ .
HPLC; Rt = 5.83min.

(Example 320)
2- [N- (2,3-Dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- (thiazol-2-yl) acetamide (Compound No. 1-1068)
The reaction was conducted in the same manner as in Example 152 using [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetic acid and 2-aminothiazole prepared in Reference Example 1. The title compound was obtained.
MS (APCI, m / z): 452 (M + H) ⁺ .
HPLC; Rt = 5.06min.

(Example 321)
2- [N- (2,3-Dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- (5-methylthiazol-2-yl) acetamide (compound of Exemplified Compound No. 1-1070)
Similar to Example 152, using [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetic acid and 2-amino-5-methylthiazole prepared in Reference Example 1. To give the title compound.
MS (APCI, m / z): 466 (M + H) ⁺ .
HPLC; Rt = 5.33min.

(Example 322)
N- (5-cyclopropyl- [1,3,4] thiadiazol-2-yl) -2- [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetamide (example Compound number 1-1088)
[N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetic acid and 5-cyclopropyl- [1,3,4] thiadiazol-2-amine prepared in Reference Example 1 Was used in the same manner as in Example 152 to obtain the title compound.
MS (APCI, m / z): 493 (M + H) ⁺ .
HPLC; Rt = 5.14min.

(Example 323)
N- (5-acetyl-4-methylthiazol-2-yl) -2- [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetamide (Exemplified Compound No. 1-1075 Compound)
Using [N = (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetic acid and 5-acetyl-2-amino-4-methylthiazole prepared in Reference Example 1 The reaction was conducted in the same manner as in Example 152 to obtain the title compound.
MS (APCI, m / z): 508 (M + H) ⁺ .
HPLC; Rt = 5.22min.

(Example 324)
N- [5- (tert-butyl)-[1,3,4] thiadiazol-2-yl] -2- [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] Acetamide (compound of Exemplified Compound No. 1-1087)
[N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetic acid prepared in Reference Example 1 and 5- (tert-butyl)-[1,3,4] thiadiazole-2 -The reaction was carried out in the same manner as in Example 152 using amine to obtain the title compound.
MS (APCI, m / z): 509 (M + H) ⁺ .
HPLC; Rt = 5.67min.

(Example 325)
2- [N- (2,3-Dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- (4-methylthiazol-2-yl) acetamide (compound of Exemplified Compound No. 1-1069)
Similar to Example 152, using [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetic acid and 2-amino-4-methylthiazole prepared in Reference Example 1. To give the title compound.
MS (APCI, m / z): 466 (M + H) ⁺ .
HPLC; Rt = 5.56min.

(Example 326)
2- [N- (2,3-Dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- (4,5-dimethylthiazol-2-yl) acetamide (Exemplified Compound No. 1-1074) )
Using [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetic acid and 2-amino-4,5-dimethylthiazole hydrochloride prepared in Reference Example 1 The reaction was conducted in the same manner as in Example 152 to obtain the title compound.
MS (APCI, m / z): 480 (M + H) ⁺ .
HPLC; Rt = 5.82min.

(Example 327)
2- [N- (2,3-Dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- (2-methyl-5-phenyl-2H-pyrazol-3-yl) acetamide (Exemplary Compound No. 1-1108 compounds)
Using [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetic acid prepared in Reference Example 1 and 5-amino-1-methyl-3-phenylpyrazole The reaction was conducted in the same manner as in Example 152 to obtain the title compound.
MS (APCI, m / z): 525 (M + H) ⁺ .
HPLC; Rt = 5.85min.

(Example 328)
2- [N- (2,3-Dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- [6- (morpholin-4-yl) pyridin-3-yl] acetamide (Exemplary Compound No. 1 -1182)
Using [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetic acid and 3-amino-6- (morpholin-4-yl) pyridine prepared in Reference Example 1 In the same manner as in Example 152, the title compound was obtained.
MS (APCI, m / z): 531 (M + H) ^<+> .
HPLC; Rt = 4.36min.

(Example 329)
2- [N- (2,3-Dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- (3-methylisothiazol-5-yl) acetamide (compound with exemplary compound number 1-1080)
Using [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetic acid and 5-amino-3-methylisothiazole hydrochloride prepared in Reference Example 1, The reaction was conducted in the same manner as in 152 to give the title compound.
MS (APCI, m / z): 466 (M + H) ⁺ .
HPLC; Rt = 5.19min.

(Example 330)
N- [4- (tert-butyl) thiazol-2-yl] -2- [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetamide (Exemplified Compound No. 1-1071 Compound)
Using [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetic acid and 2-amino-4- (tert-butyl) thiazole prepared in Reference Example 1 The reaction was conducted in the same manner as in Example 152 to obtain the title compound.
MS (APCI, m / z): 508 (M + H) ⁺ .
HPLC; Rt = 6.80min.

(Example 331)
2- [N- (2,3-Dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- (4-phenylthiazol-2-yl) acetamide (compound of Exemplified Compound No. 1-112)
Similar to Example 152, using [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetic acid and 2-amino-4-phenylthiazole prepared in Reference Example 1. To give the title compound.
MS (APCI, m / z): 528 (M + H) ⁺ .
HPLC; Rt = 6.60min.

(Example 332)
2- [N- (2,3-Dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- [2-methyl-5- (thiophen-2-yl) -2H-pyrazol-3-yl ] Acetamide (compound of Exemplified Compound No. 1-1122)
[N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetic acid prepared in Reference Example 1 and 1-methyl-3- (2-thienyl) -1H-pyrazole-5 -The reaction was carried out in the same manner as in Example 152 using amine to obtain the title compound.
MS (APCI, m / z): 531 (M + H) ^<+> .
HPLC; Rt = 5.74min.

(Example 333)
[2- [2- [N- (2,3-Dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetylamino] thiazol-4-yl] acetic acid ethyl ester (compound of Exemplified Compound No. 1-1073 )
Using [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetic acid and (2-amino-4-thiazolyl) acetic acid ethyl ester prepared in Reference Example 1 The reaction was conducted in the same manner as in Example 152 to obtain the title compound.
MS (APCI, m / z): 538 (M + H) ⁺ .
HPLC; Rt = 5.68min.

(Example 334)
2- [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- (2-methyl-2H-pyrazol-3-yl) acetamide (Exemplary Compound No. 1-1060 Compound)
Using [N- (2,3-dimethylphenyl) -N- (naphthalen-1-sulfonyl) amino] acetic acid and (1-methyl-1H-pyrazol-5-yl) amine prepared in Reference Example 1 In the same manner as in Example 152, the title compound was obtained.
MS (APCI, m / z): 449 (M + H) ⁺ .
HPLC; Rt = 4.77min.

(Example 335)
2- [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- (2,5-dimethyl-2H-pyrazol-3-yl) acetamide (Exemplary Compound No. 1- 1061 compounds)
Using [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetic acid and 5-amino-1,3-dimethylpyrazole prepared in Reference Example 1, Example 152 To give the title compound.
MS (APCI, m / z): 463 (M + H) ⁺ .
HPLC; Rt = 4.88min.

(Example 336)
N- (5-cyclopropyl-2-methyl-2H-pyrazol-3-yl) -2- [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetamide (exemplary compound Compound number 1-1062)
[N- (2,3-Dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetic acid and 3-cyclopropyl-1-methyl-1H-pyrazol-5-amine prepared in Reference Example 1 And the reaction was carried out in the same manner as in Example 152 to obtain the title compound.
MS (APCI, m / z): 489 (M + H) ⁺ .
HPLC; Rt = 5.22min.

(Example 337)
N- [5- (tert-butyl) isoxazol-3-yl] -2- [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetamide (Exemplified Compound No. 1-1067 Compound)
Using [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetic acid prepared in Reference Example 1 and 5- (tert-butyl) isoxazol-3-amine The reaction was conducted in the same manner as in Example 152 to obtain the title compound.
MS (APCI, m / z): 492 (M + H) ⁺ .
HPLC; Rt = 6.40min.

(Example 338)
5- [2- [N- (2,3-Dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetylamino] furan-2-carboxylic acid methyl ester (compound of Exemplified Compound No. 1-1057)
Using [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetic acid and 5-aminofuran-2-carboxylic acid methyl ester prepared in Reference Example 1, The reaction was conducted in the same manner as in 152 to give the title compound.
MS (APCI, m / z): 493 (M + H) ⁺ .
HPLC; Rt = 5.58min.

(Example 339)
2- [N- (2,3-Dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- [4- (5-methylthiophen-2-yl) -1,3-thiazol-2- Yl] acetamide (compound of Exemplified Compound No. 1-1153)
[N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetic acid prepared in Reference Example 1 and [4- (5-methylthiophen-2-yl) -1,3 Using -thiazol-2-yl] amine, the reaction was carried out in the same manner as in Example 152 to obtain the title compound.
MS (APCI, m / z): 548 (M + H) ⁺ .
HPLC; Rt = 6.78min.

(Example 340)
N- [4- (4-Bromo-1-methyl-1H-pyrazol-3-yl) phenyl] -2- [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] Acetamide (compound of Exemplified Compound No. 1-779)
[N- (2,3-Dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetic acid and 3- (4-aminophenyl) -4-bromo-1-methylpyrazole prepared in Reference Example 1 Was used in the same manner as in Example 152 to obtain the title compound.
MS (APCI, m / z): 603 (M + H) ⁺ , 605 (M + H) ⁺ .
HPLC; Rt = 6.17min.

(Example 341)
N- [4- (4,5-dichloroimidazol-1-yl) phenyl] -2- [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetamide (Exemplary Compound No. 1-991 compounds)
[N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetic acid prepared in Reference Example 1 and 4- (4,5-dichloro-1H-imidazol-1-yl) The reaction was carried out in the same manner as in Example 152 using aniline to obtain the title compound.
MS (APCI, m / z): 579 (M + H) ⁺ , 581 (M + H) ⁺ .
HPLC; Rt = 6.21min.

(Example 342)
2- [N- (2,3-Dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- [4-([1,2,3] thiadiazol-4-yl) phenyl] acetamide (example) Compound number 1-1012)
[N- (2,3-Dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetic acid and 4-([1,2,3] thiadiazol-4-yl) aniline prepared in Reference Example 1 Was used in the same manner as in Example 152 to obtain the title compound.
MS (APCI, m / z): 529 (M + H) ⁺ .
HPLC; Rt = 5.94min.

(Example 343)
2- [N- (2,3-Dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- [4- (pyrrol-1-yl) phenyl] acetamide (Compound of Exemplified Compound No. 1-719) )
Using [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetic acid and 4- (1H-pyrrol-1-yl) aniline prepared in Reference Example 1 The reaction was conducted in the same manner as in Example 152 to obtain the title compound.
MS (APCI, m / z): 510 (M + H) ⁺ .
HPLC; Rt = 6.43min.

(Example 344)
2- [N- (2,3-Dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- [4- (pyrazol-1-yl) phenyl] acetamide (Exemplified Compound No. 1-750) )
Using [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetic acid and 4- (1H-pyrazol-1-yl) aniline prepared in Reference Example 1 The reaction was conducted in the same manner as in Example 152 to obtain the title compound.
MS (APCI, m / z): 511 (M + H) ⁺ .
HPLC; Rt = 5.75min.

(Example 345)
2- [N- (2,3-Dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- [4- (1,3-oxazol-5-yl) phenyl] acetamide (Exemplary Compound No. 1 -993 compounds)
Using [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetic acid and 4- (1,3-oxazol-5-yl) aniline prepared in Reference Example 1 In the same manner as in Example 152, the title compound was obtained.
MS (APCI, m / z): 512 (M + H) ⁺ .
HPLC; Rt = 5.56min.

(Example 346)
2- [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- [4-([1,2,4] triazol-1-yl) phenyl] acetamide (example Compound No. 1-1004)
[N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetic acid and 4-([1,2,4] triazol-1-yl) aniline prepared in Reference Example 1 And the reaction was carried out in the same manner as in Example 152 to obtain the title compound.
MS (APCI, m / z): 512 (M + H) ⁺ .
HPLC; Rt = 5.10min.

(Example 347)
2- [N- (2,3-Dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- [4- (3,5-dimethyl-1H-pyrazol-1-yl) phenyl] acetamide ( Compound of Exemplified Compound No. 1-774)
[N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetic acid prepared in Reference Example 1 and 4- (3,5-dimethyl-1H-pyrazol-1-yl) Reaction was carried out in the same manner as in Example 152 using aniline to obtain the title compound.
MS (APCI, m / z): 539 (M + H) ⁺ .
HPLC; Rt = 5.89min.

(Example 348)
2- [N = (2,3-Dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- [4- (4-methylpiperazin-1-yl) phenyl] acetamide (Exemplary Compound No. 1- 1027 compounds)
Using [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetic acid and 4- (4-methylpiperazin-1-yl) aniline prepared in Reference Example 1, The reaction was conducted in the same manner as in Example 152 to obtain the title compound.
MS (APCI, m / z): 543 (M + H) ⁺ .
HPLC; Rt = 3.91 min.

(Example 349)
5- [4- [2- [N- (2,3-Dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetylamino] phenyl] -2-methylfuran-3-carboxylic acid ethyl ester (illustrated Compound number 1-740)
[N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetic acid and 5- (4-aminophenyl) -2-methylfuran-3-carboxylic acid prepared in Reference Example 1 The reaction was carried out in the same manner as in Example 152 using acid ethyl ester to obtain the title compound.
MS (APCI, m / z): 597 (M + H) ⁺ .
HPLC; Rt = 7.17 min.

(Example 350)
1- [4- [2- [N- (2,3-Dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetylamino] phenyl] -3,5-dimethyl-1H-pyrazole-4-carboxyl Acid ethyl ester (compound of Exemplified Compound No. 1-780)
[N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetic acid prepared in Reference Example 1 and 1- (4-aminophenyl) -3,5-dimethyl-1H- The title compound was obtained by reacting in the same manner as in Example 152 using pyrazole-4-carboxylic acid ethyl ester.
MS (APCI, m / z): 611 (M + H) ⁺ .
HPLC; Rt = 6.49min.

(Example 351)
1- [4- [2- [N- (2,3-Dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetylamino] phenyl] -5-methyl-1H-pyrazole-4-carboxylate ethyl Ester (Exemplified Compound No. 1-776)
[N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetic acid prepared in Reference Example 1 and 1- (4-aminophenyl) -5-methyl-1H-pyrazole- The title compound was obtained by reacting in the same manner as in Example 152 using 4-carboxylic acid ethyl ester.
MS (APCI, m / z): 597 (M + H) ⁺ .
HPLC; Rt = 6.26min.

(Example 352)
2- [N- (4-Bromo-1-methyl-1H-pyrazol-3-yl) -N- (naphthalene-1-sulfonyl) amino] -N- (4-ethoxyphenyl) acetamide (Exemplary Compound No. 1- 415 compounds)
The title compound was obtained in the same manner as in Example 227 using 3-amino-4-bromo-1-methylpyrazole.
MS (APCI, m / z): 543 (M + H) ⁺ , 545 (M + H) ⁺ .
HPLC; Rt = 5.51min.

(Example 353)
N- (4-Ethoxyphenyl) -2- [N- (4-methylthiazol-2-yl) -N- (naphthalene-1-sulfonyl) amino] acetamide (compound of exemplary compound number 1-424)
The title compound was obtained in the same manner as in Example 227 using 2-amino-4-methylthiazole.
MS (APCI, m / z): 482 (M + H) ⁺ .
HPLC; Rt = 4.74min.

(Example 354)
2- [N- (4,5-Dimethylthiazol-2-yl) -N- (naphthalene-1-sulfonyl) amino] -N- (4-ethoxyphenyl) acetamide (compound of Exemplified Compound No. 1-427)
2-amino-4,5-dimethylthiazole hydrochloride was used in the same manner as in Example 227 to obtain the title compound.
MS (APCI, m / z): 496 (M + H) ⁺ .
HPLC; Rt = 4.99min.

(Example 355)
2- [N- (5-acetyl-4-methylthiazol-2-yl) -N- (naphthalene-1-sulfonyl) amino] -N- (4-ethoxyphenyl) acetamide (Compound of Exemplified Compound No. 1-428 )
Using 5-acetyl-2-amino-4-methylthiazole, the reaction was carried out in the same manner as in Example 227 to obtain the title compound.
MS (APCI, m / z): 524 (M + H) ⁺ .
HPLC; Rt = 4.89min.

(Example 356)
2-[[5- (tert-Butyl) isoxazol-3-yl] -N- (naphthalene-1-sulfonyl) amino] -N- (4-ethoxyphenyl) acetamide (compound of Exemplified Compound No. 1-422)
The title compound was obtained in the same manner as in Example 227 using 5- (tert-butyl) isoxazol-3-amine.
MS (APCI, m / z): 508 (M + H) ⁺ .
HPLC; Rt = 6.19min.

(Example 357)
2- [N- (2,3-Dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- [4- (4-methyl-5-thioxo-4,5-dihydro-1H- [1 , 2,4] Triazol-3-yl) phenyl] acetamide (compound of Exemplified Compound No. 1-1043)
[N- (2,3-Dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetic acid prepared in Reference Example 1 and 5- (4-aminophenyl) -4- prepared in Reference Example 16 The title compound was obtained in the same manner as in Example 152 using methyl-2,4-dihydro- [1,2,4] triazole-3-thione.
¹ H-NMR (DMSO-d ₆ ) δ: 10.24 (s, 1H), 8.31 (d, 1H, J = 3.8Hz), 8.28 (d, 1H, J = 3.0Hz), 8.10 (d like, 2H, J = 8.1Hz), 7.69-7.59 (m, 6H), 7.49 (dd like, 1H, J = 8.6, 7.3Hz), 7.11 (dd, 1H, J = 4.6, 4.1Hz), 6.94 (d, 2H, J = 4.3Hz), 4.61 (d, 1H, J = 16.7Hz), 4.38 (d, 1H, J = 16.7Hz), 3.51 (s, 3H), 2.13 (s, 3H), 1.83 (s, 3H) .
MS (APCI, m / z): 558 (M + H) ^<+> .
HPLC; Rt = 5.05min.

(Example 358)
2- [N- (5-Cyclopropyl- [1,3,4] thiadiazol-2-yl) -N- (naphthalene-1-sulfonyl) amino] -N- (4-ethoxyphenyl) acetamide (Exemplary Compound No. 1-432 compounds)
The title compound was obtained in the same manner as in Example 227 using 5-cyclopropyl- [1,3,4] thiadiazol-2-amine.
MS (APCI, m / z): 509 (M + H) ⁺ .
HPLC; Rt = 5.26min.

(Example 359)
3- [N- [N- (4-Ethoxyphenyl) carbamoyl] methyl-N- (naphthalene-1-sulfonyl) amino] thiophene-2-carboxylic acid methyl ester (compound of Exemplified Compound No. 1-411)
Using 2-methylthiophene-3-carboxylic acid methyl ester, the reaction was carried out in the same manner as in Example 227 to obtain the title compound.
MS (APCI, m / z): 525 (M + H) ⁺ .
HPLC; Rt = 5.72min.

(Example 360)
2- [N- [5- (tert-butyl)-[1,3,4] thiadiazol-2-yl] -N- (naphthalene-1-sulfonyl) amino] -N- (4-ethoxyphenyl) acetamide ( Compound of Exemplified Compound No. 1-431)
The title compound was obtained in the same manner as in Example 227 using 5- (tert-butyl)-[1,3,4] thiadiazol-2-amine.
MS (APCI, m / z): 525 (M + H) ⁺ .
HPLC; Rt = 5.78min.

(Example 361)
[2- [N- [N- (4-Ethoxyphenyl) carbamoyl] methyl-N- (naphthalen-1-sulfonyl) amino] thiazol-4-yl] acetic acid ethyl ester (compound of Exemplified Compound No. 1-426)
(2-Aminothiazol-4-yl) acetic acid Ethyl ester was used in the same manner as in Example 227 to obtain the title compound.
MS (APCI, m / z): 554 (M + H) ⁺ .
HPLC; Rt = 5.00min.

(Example 362)
N- (4-Ethoxyphenyl) -2- [N- (2-methyl-2H-pyrazol-3-yl) -N- (naphthalene-1-sulfonyl) amino] acetamide (compound of Exemplified Compound No. 1-413)
(1-Methyl-1H-pyrazol-5-yl) amine was used in the same manner as in Example 227 to obtain the title compound.
MS (APCI, m / z): 465 (M + H) ⁺ .
HPLC; Rt = 4.85min.

(Example 363)
N- (4-Ethoxyphenyl) -2- [N- (5-methylisoxazol-3-yl) -N- (naphthalene-1-sulfonyl) amino] acetamide (compound of Exemplified Compound No. 1-420)
The title compound was obtained in the same manner as in Example 227 using 3-amino-5-methylisoxazole.
MS (APCI, m / z): 466 (M + H) ⁺ .
HPLC; Rt = 5.34min.

(Example 364)
2- [N- (2,5-dimethyl-2H-pyrazol-3-yl) -N- (naphthalene-1-sulfonyl) amino] -N- (4-ethoxyphenyl) acetamide (Exemplary Compound No. 1-414 Compound)
The title compound was obtained in the same manner as in Example 227 using 5-amino-1,3-dimethylpyrazole.
MS (APCI, m / z): 479 (M + H) ⁺ .
HPLC; Rt = 4.95min.

(Example 365)
N- (4-Ethoxyphenyl) -2- [N- (2-methyl-5-phenyl-2H-pyrazol-3-yl) -N- (naphthalene-1-sulfonyl) amino] acetamide (Exemplary Compound No. 1- 482 compounds)
The title compound was obtained in the same manner as in Example 227 using 5-amino-1-methyl-3-phenylpyrazole.
MS (APCI, m / z): 541 (M + H) ⁺ .
HPLC; Rt = 5.89min.

(Example 366)
2- [N- (4-Bromo-5-methylisoxazol-3-yl) -N- (naphthalene-1-sulfonyl) amino] -N- (4-ethoxyphenyl) acetamide (Exemplary Compound No. 1-421 Compound)
The title compound was obtained in the same manner as in Example 227 using 4-bromo-5-methylisoxazol-3-amine.
MS (APCI, m / z): 544 (M + H) ⁺ , 546 (M + H) ⁺ .
HPLC; Rt = 5.71min.

(Example 367)
2- [N- (2,3-Dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] -N- (3-phenyl- [1,2,4] thiadiazol-5-yl) acetamide (Exemplary compound Compound number 1-1115)
[N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetic acid prepared in Reference Example 1 and (3-phenyl- [1,2,4] thiadiazol-5-yl ) The amine was used and reacted in the same manner as in Example 152 to obtain the title compound.
MS (APCI, m / z): 529 (M + H) ⁺ .
HPLC; Rt = 6.58min.

(Example 368)
N- [4- (4-Chlorophenyl) -5-methylthiazol-2-yl] -2- [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetamide (Exemplary compound Compound number 1-1113)
[N- (2,3-Dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetic acid prepared in Reference Example 1 and [4- (4-chlorophenyl) -5- Methylthiazol-2-yl] amine was used in the same manner as in Example 152 to obtain the title compound.
MS (APCI, m / z): 576 (M + H) ⁺ , 578 (M + H) ⁺ .
HPLC; Rt = 7.29 min.

(Example 369)
2- [4- [2- [N- (2,3-Dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetylamino] phenyl] -1,3-oxazole-4-carboxylic acid ethyl ester ( Compound of Exemplified Compound Number 1-998)
[N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetic acid prepared in Reference Example 1 and 2- (4-aminophenyl) -1,3-oxazole-4- The title compound was obtained in the same manner as in Example 152 using carboxylic acid ethyl ester.
MS (APCI, m / z): 584 (M + H) ^<+> .
HPLC; Rt = 6.13min.

(Example 370)
N- [4- (imidazol-1-yl) phenyl] -2- [N- (2-methoxypyridin-3-yl) -N- (naphthalene-1-sulfonyl) amino] acetamide (Exemplified Compound No. 1-833 Compound)
Using [N- (2-methoxypyridin-3-yl) -N- (naphthalen-1-sulfonyl) amino] acetic acid and 4- (1H-imidazol-1-yl) aniline prepared in Reference Example 20 In the same manner as in Example 152, the title compound was obtained.
MS (APCI, m / z): 514 (M + H) ⁺ .
HPLC; Rt = 3.51min.

(Example 371)
N- [4- (4,5-dichloroimidazol-1-yl) phenyl] -2- [N- (2,3-dimethylphenyl) -N- (quinoline-8-sulfonyl) amino] acetamide (Exemplary Compound No. 1-992 compounds)
[N- (2,3-dimethylphenyl) -N- (quinolin-8-sulfonyl) amino] acetic acid prepared in Reference Example 11 and 4- (4,5-dichloro-1H-imidazol-1-yl) The reaction was carried out in the same manner as in Example 152 using aniline to obtain the title compound.
MS (APCI, m / z): 580 (M + H) ⁺ , 582 (M + H) ⁺ .
HPLC; Rt = 5.51min.

(Example 372)
2- [N- (2,3-Dimethylphenyl) -N- (quinolin-8-sulfonyl) amino] -N- [4- (1,3-oxazol-5-yl) phenyl] acetamide (Exemplary Compound No. 1 -994 compounds)
Using [N- (2,3-dimethylphenyl) -N- (quinolin-8-sulfonyl) amino] acetic acid and 4- (1,3-oxazol-5-yl) aniline prepared in Reference Example 11 In the same manner as in Example 152, the title compound was obtained.
MS (APCI, m / z): 513 (M + H) ⁺ .
HPLC; Rt = 4.86min.

(Example 373)
2- [N- (2,3-Dimethylphenyl) -N- (quinolin-8-sulfonyl) amino] -N- [4-([1,2,4] triazol-1-yl) phenyl] acetamide (illustrated Compound No. 1-1005)
[N- (2,3-dimethylphenyl) -N- (quinolin-8-sulfonyl) amino] acetic acid and 4-([1,2,4] triazol-1-yl) aniline prepared in Reference Example 11 And the reaction was carried out in the same manner as in Example 152 to obtain the title compound.
MS (APCI, m / z): 513 (M + H) ⁺ .
HPLC; Rt = 4.43min.

(Example 374)
1- [4- [2- [N- (2,3-Dimethylphenyl) -N- (quinoline-8-sulfonyl) amino] acetylamino] phenyl] -5-methyl-1H-pyrazole-4-carboxylate ethyl Esters (compounds with exemplary compound number 1-777)
[N- (2,3-dimethylphenyl) -N- (quinoline-8-sulfonyl) amino] acetic acid prepared in Reference Example 11 and 1- (4-aminophenyl) -5-methyl-1H-pyrazole- The title compound was obtained in the same manner as in Example 152 using 4-carboxylic acid ethyl ester.
MS (APCI, m / z): 598 (M + H) ⁺ .
HPLC; Rt = 5.57min.

(Example 375)
2- [N- (2,3-Dimethylphenyl) -N- (quinoline-8-sulfonyl) amino] -N- [4- (4-methyl-5-thioxo-4,5-dihydro-1H- [1 , 2,4] triazol-3-yl) phenyl] acetamide (compound of Exemplified Compound No. 1-1045)
[N- (2,3-Dimethylphenyl) -N- (quinoline-8-sulfonyl) amino] acetic acid prepared in Reference Example 11 and 5- (4-aminophenyl) -4- prepared in Reference Example 16 The title compound was obtained in the same manner as in Example 152 using methyl-2,4-dihydro- [1,2,4] triazole-3-thione.
MS (APCI, m / z): 559 (M + H) ⁺ .
HPLC; Rt = 4.44min.

(Example 376)
2- [N- (2,3-Dimethylphenyl) -N- (4-fluoronaphthalene-1-sulfonyl) amino] -N- [4- (imidazol-1-yl) phenyl] acetamide (Exemplary Compound No. 1- 802 compounds)
Using [N- (2,3-dimethylphenyl) -N- (4-fluoronaphthalene-1-sulfonyl) amino] acetic acid and 4- (1H-imidazol-1-yl) aniline prepared in Reference Example 22 In the same manner as in Example 152, the title compound was obtained.
MS (APCI, m / z): 529 (M + H) ⁺ .
HPLC; Rt = 4.05min.

(Example 377)
N- [4- (imidazol-1-yl) phenyl] -2- [N- (2-oxo-1,2-dihydropyridin-3-yl) -N- (quinoline-8-sulfonyl) amino] acetamide (illustrated Compound number 1-872)
N- [4- (imidazol-1-yl) phenyl] -2- [N- (2-methoxypyridin-3-yl) -N- (quinolin-8-sulfonyl) amino] acetamide (prepared in Example 286) 100 mg, 0.194 mmol) was dissolved in 1,4-dioxane-water (1: 2, 3.0 ml), 4N hydrochloric acid-1,4-dioxane solution (1.0 ml) was added, and the mixture was stirred at 50 ° C. for 24 hours. . The reaction mixture was diluted with ethyl acetate and washed with saturated aqueous sodium hydrogen carbonate and saturated brine. The organic layer was dried over anhydrous sodium sulfate, the solvent was concentrated under reduced pressure, and the obtained residue was washed with a mixed solvent of diethyl ether-ethyl acetate to obtain the title compound.
MS (APCI, m / z): 501 (M + H) ⁺ .
HPLC; Rt = 2.67min.

(Reference Example 1)
[N- (2,3-Dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetic acid Naphthalene-1-sulfonic acid (2,3-dimethylphenyl) amide prepared in Reference Example 2 (3.00 g, 9.63 mmol) was dissolved in N, N-dimethylformamide (60 ml), bromoacetic acid (tert-butyl) ester (1.85 ml, 12.5 mmol) was added, and the mixture was cooled to 0 ° C., and then potassium carbonate (4.00 g, 28.9 mmol). And stirred for 16 hours while slowly warming from 0 ° C. to room temperature. The reaction mixture was diluted with ethyl acetate and washed with water and saturated brine. The organic layer was dried over anhydrous sodium sulfate and purified by simple silica gel filtration using ethyl acetate. The solvent was concentrated under reduced pressure, and [N- (2,3-dimethylphenyl) -N- (naphthalene -1-sulfonyl) amino] acetic acid (tert-butyl) ester was obtained. This compound was used in the next reaction without purification.
The obtained [N- (2,3-dimethylphenyl) -N- (naphthalene-1-sulfonyl) amino] acetic acid (tert-butyl) ester was dissolved in dichloromethane (20 ml) and cooled to 0 ° C. 50% trifluoroacetic acid (20 ml) was added in dichloromethane, and the mixture was stirred for 3 hours while slowly warming from 0 ° C. to room temperature. The reaction mixture was diluted with dichloromethane and washed with water and saturated brine. The organic layer was dried over anhydrous sodium sulfate, the solvent was concentrated under reduced pressure, and the obtained residue was washed with a mixed solvent of n-hexane-diisopropyl ether to give the title compound (3.50 g, total yield 98%). Got.
¹ H-NMR (CDCl ₃ ) δ: 8.34 (d, 1H, J = 8.1Hz), 8.27 (dd, 1H, J = 7.3, 1.1Hz), 8.06 (d, 1H, J = 8.4Hz), 7.89 ( d, 1H, J = 7.8Hz), 7.56-7.36 (m, 3H), 7.09 (dd, 1H, J = 5.1, 3.8Hz), 6.95-6.87 (m, 2H), 4.57 (d, 1H, J = 18.1Hz), 4.17 (d, 1H, J = 18.1Hz), 2.17 (s, 3H), 1.86 (s, 3H).
MS (APCI, m / z): 370 (M + H) ⁺ .
HPLC; Rt = 4.76min.

(Reference Example 2)
Naphthalene-1-sulfonic acid [N- (2,3-dimethylphenyl)] amide
2,3-dimethylaniline (5.00 g, 41.3 mmol) was dissolved in dichloromethane (100 ml), 1-naphthalenesulfonyl chloride (7.48 g, 33.0 mmol) was added, and the mixture was cooled to 0 ° C., and then pyridine (3.0 ml, 37.2 mmol). mmol) and 4- (dimethylamino) pyridine (catalytic amount, about 20 mg) were added, and the mixture was stirred for 14 hours while slowly warming from 0 ° C. to room temperature. The reaction mixture was diluted with dichloromethane and washed with 1N hydrochloric acid and saturated brine. The organic layer is dried over anhydrous sodium sulfate and purified by silica gel filtration using ethyl acetate. The solvent is concentrated under reduced pressure, and the resulting residue is washed with an n-hexane-ethyl acetate mixed solvent. This gave the title compound (9.41 g, 91%).
MS (APCI, m / z): 312 (M + H) ⁺ .
HPLC; Rt = 5.34min.

(Reference Example 3)
[N- (Naphthalene-1-sulfonyl) -N- (3-trifluoromethylphenyl) amino] acetic acid Naphthalene-1-sulfonic acid [N- (3-trifluoromethylphenyl)] amide prepared in Reference Example 4 The reaction was carried out in the same manner as in Reference Example 1 to obtain the title compound.
¹ H-NMR (CDCl ₃ ) δ: 8.33 (d, 1H, J = 8.4Hz), 8.12 (d, 1H, J = 7.3), 8.08 (d, 1H, J = 8.1Hz), 7.93 (d, 1H , J = 7.8Hz), 7.62-7.34 (m, 7H), 4.52 (s, 2H).
MS (APCI, m / z): 408 (MH) ⁺ .
HPLC; Rt = 4.93min.

(Reference Example 4)
Naphthalene-1-sulfonic acid [N- (3-trifluoromethylphenyl)] amide
The reaction was carried out in the same manner as in Reference Example 2 using 3-trifluoromethylaniline to obtain the title compound.
MS (APCI, m / z): 350 (MH) ⁺ .
HPLC; Rt = 5.40min.

(Reference Example 5)
N- (4-Ethoxyphenyl) -2- [N- (3-trifluoromethylphenyl) amino] acetamide
The reaction was carried out in the same manner as in Reference Example 6 using 3-trifluoromethylaniline to obtain the title compound.
MS (APCI, m / z): 339 (M + H) ⁺ .
HPLC; Rt = 4.90min.

(Reference Example 6)
2- [N- (2,3-Dimethylphenyl) amino] -N- (4-ethoxyphenyl) acetamide monohydrochloride 2- [N- (2,3-dimethylphenyl) -N- prepared in Reference Example 8 (2,4-Dinitrobenzenesulfonyl) amino] -N- (4-ethoxyphenyl) acetamide was dissolved in dichloromethane (40 ml), thioglycolic acid (0.79 ml, 11.4 mmol) was added and cooled to 0 ° C. Triethylamine (3.13 ml, 22.8 mmol) was added, and the mixture was stirred for 17 hours while slowly warming from 0 ° C. to room temperature. The reaction mixture was diluted with ethyl acetate and washed with saturated aqueous sodium hydrogen carbonate, water and saturated brine. The organic layer was dried over anhydrous sodium sulfate and purified by simple silica gel filtration using ethyl acetate. The solvent was concentrated under reduced pressure, and 2- [N- (2,3-dimethylphenyl) amino]- N- (4-ethoxyphenyl) acetamide was obtained.
This compound was dissolved in ethyl acetate (40 ml), 4N hydrochloric acid-ethyl acetate solution (1.5 ml, 6.0 mmol) was added, and the mixture was stirred at room temperature for 10 min. The reaction solution was suspended by adding a mixed solvent of diethyl ether-n-hexane, and the precipitated solid was collected by filtration and washed with diethyl ether to obtain the title compound (840 mg, total yield 44%).
MS (APCI, m / z): 299 (M + H) ⁺ .
HPLC; Rt = 5.06min.

(Reference Example 7)
2-Bromo-N- (4-ethoxyphenyl) acetamide p-phenetidine (1.00 g, 7.29 mmol) was dissolved in N, N-dimethylacetamide (20 ml), cooled to 0 ° C., and then bromoacetyl bromide (0.95 ml, 10.9 mmol) was added, and the mixture was stirred for 15 hours while slowly warming from 0 ° C to room temperature. The reaction mixture was diluted with ethyl acetate and washed with water, saturated aqueous sodium hydrogen carbonate, and saturated brine. The organic layer is dried over anhydrous sodium sulfate and purified by silica gel filtration using ethyl acetate. The solvent is concentrated under reduced pressure, and the resulting residue is washed with an n-hexane-ethyl acetate mixed solvent. This gave the title compound (1.56 g, 83%).
MS (APCI, m / z): 258, 260 (M + H) ⁺ .
HPLC; Rt = 3.76min.

(Reference Example 8)
2- [N- (2,3-Dimethylphenyl) -N- (2,4-dinitrobenzenesulfonyl) amino] -N- (4-ethoxyphenyl) acetamide N- (2,3- Dimethylphenyl) -2,4-dinitrobenzenesulfonamide (2.00 g, 5.69 mmol) was dissolved in N, N-dimethylacetamide (20 ml) and 2-bromo-N- (4-ethoxyphenyl) acetamide (1.91 g , 7.40 mmol) and cooled to 0 ° C., sodium hydrogen carbonate (2.39 g, 28.5 mmol) was added, and the mixture was stirred for 22 hours while slowly warming from 0 ° C. to room temperature. The reaction mixture was diluted with ethyl acetate and washed with water, 1N hydrochloric acid and saturated brine. The organic layer was dried over anhydrous magnesium sulfate and then purified by simple silica gel filtration using ethyl acetate, and the solvent was concentrated under reduced pressure to obtain the title compound. This compound was used in the next reaction without purification.
MS (APCI, m / z): 529 (M + H) ⁺ .
HPLC; Rt = 5.65min.

(Reference Example 9)
N- (2,3-Dimethylphenyl) -2,4-dinitrobenzenesulfonamide
Using 2,4-dinitrobenzenesulfonyl chloride, the reaction was carried out in the same manner as in Reference Example 2 to obtain the title compound.
MS (APCI, m / z): 350 (MH) ⁺ .
HPLC; Rt = 5.00min.

(Reference Example 10)
2-Bromo- [N- (4-methoxyphenyl) -N-methyl] acetamide
N-methyl-para-anisidine (3.00 g, 21.9 mmol) was dissolved in N, N-dimethylacetamide (60 ml), cooled to 0 ° C., bromoacetyl bromide (2.86 ml, 32.8 mmol) was added, and 0 The mixture was stirred for 18 hours while slowly warming from ° C to room temperature. The reaction mixture was diluted with ethyl acetate and washed with water, saturated aqueous sodium hydrogen carbonate, and saturated brine. The organic layer was dried over anhydrous sodium sulfate and then simply purified by silica gel filtration using ethyl acetate, and the solvent was concentrated under reduced pressure to obtain the title compound (5.73 g, quant.).
MS (APCI, m / z): 258, 260 (M + H) ⁺ .
HPLC; Rt = 3.83min.

(Reference Example 11)
[N- (2,3-dimethylphenyl) -N- (quinoline-8-sulfonyl) amino] acetic acid The quinoline-8-sulfonic acid [N- (2,3-dimethylphenyl)] amide prepared in Reference Example 12 And the reaction was carried out in the same manner as in Reference Example 13 to obtain the title compound.
MS (APCI, m / z): 371 (M + H) ⁺ .
HPLC; Rt = 4.09min.

(Reference Example 12)
Quinoline-8-sulfonic acid [N- (2,3-dimethylphenyl)] amide
The reaction was carried out in the same manner as in Reference Example 14 using 2,3-dimethylaniline to obtain the title compound. MS (APCI, m / z): 313 (M + H) ⁺ .
HPLC; Rt = 4.86min.

(Reference Example 13)
[N- (2-methoxypyridin-3-yl) -N- (quinoline-8-sulfonyl) amino] acetic acid Quinoline-8-sulfonic acid obtained in Reference Example 14 [N- (2-methoxypyridin-3- Yl)] amide (3.36 g, 10.1 mmol) dissolved in N, N-dimethylformamide (50 ml), bromoacetic acid (tert-butyl) ester (1.92 ml, 13.0 mmol) was added, and the mixture was cooled to 0 ° C. Potassium carbonate (5.53 g, 14.0 mmol) was added, and the mixture was stirred for 4 hours while slowly warming from 0 ° C. to room temperature. The reaction mixture was diluted with ethyl acetate and washed with water, saturated aqueous sodium hydrogen carbonate, and saturated brine. The organic layer was dried over anhydrous sodium sulfate and purified by simple silica gel filtration using ethyl acetate. The solvent was concentrated under reduced pressure, and [N- (2-methoxypyridin-3-yl) -N- (Quinolin-8-sulfonyl) amino] acetic acid (tert-butyl) ester was obtained. This compound was used in the next reaction without purification.
The obtained [N- (2-methoxypyridin-3-yl) -N- (quinolin-8-sulfonyl) amino] acetic acid (tert-butyl) ester was dissolved in dichloromethane (20 ml) and cooled to 0 ° C. 50% trifluoroacetic acid (20 ml) was added in dichloromethane, and the mixture was stirred for 30 hours while slowly warming from 0 ° C. to room temperature. The reaction solution is concentrated under reduced pressure, and the resulting residue is dissolved in dichloromethane and washed with water. The organic layer is concentrated under reduced pressure to obtain the title compound (3.66 g, 2 steps: quant.). It was. This compound was used in the next reaction without purification.
MS (APCI, m / z): 374 (M + H) ⁺ .
HPLC; Rt = 3.44min.

(Reference Example 14)
Quinoline-8-sulfonic acid [N- (2-methoxypyridin-3-yl)] amide
3-Amino-2-methoxypyridine (1.24 g, 10.0 mmol) was dissolved in pyridine (30 ml), 8-quinolinesulfonyl chloride (2.96 g, 13.0 mmol) was added, and the mixture was stirred at 60 ° C. for 18 hours. The reaction mixture was diluted with ethyl acetate and washed with saturated aqueous sodium hydrogen carbonate and saturated brine. The organic layer was dried over anhydrous sodium sulfate and purified by simple silica gel filtration using ethyl acetate, and the solvent was concentrated under reduced pressure to obtain the title compound (3.36 g, quant.). This compound was used in the next reaction without purification.
MS (APCI, m / z): 316 (M + H) ⁺ .
HPLC; Rt = 4.24min.

(Reference Example 15)
(4-Aminophenoxy) acetic acid (tert-butyl) ester
Renodon-Corniere, Axelle; Dijols, Sil vie; Perollier, Celine; Lefevre-Groboillot, David; Boucher, Jean-Luc; Attias, Roger; Sari, Marie-Agnes; Stuehr, Dennis; Mansuy, Daniel; J. Med. Chem .; 2002, 45, 4, p.944-954, Ono, Shin'ichiro; Inoue, Yoshihisa; Yoshida, Tomohiro; Ashimori, Atsuyuki; Kosaka, Keigo; Imada, Teruaki; Fukaya, Chikara; Nakamura, Norifumi; Chem. Pharm. Bull .; 1999, 47, 12, 1685-1693; Asagarasu, Akira; Takayanagi, Nao; Achiwa, Kazuo; Chem. Pharm. Bull., 1998, 46, No. 5, p.867-870; Asagarasu, Akira; Uchiyama, Taketo; Achiwa, Kazuo; Chem. Pharm. Bull .; 1998, Vol. 46, No. 4, p. It can be produced according to the methods described.

(Reference Example 16)
5- (4-Aminophenyl) -4-methyl-2,4-dihydro- [1,2,4] triazole-3-thione
Kuascuekguezel, S. Gueniz; Rollas, Sevim; Farmaco, 2002, 57, 7, p.583-588; Kuecuekguezel, Ilkay; Kuecuekguezel, S. Gueniz; Rollas, Sevim; Kiraz, Muammer; Bioorg. Med Chem. Lett, 2001, 11, 13, p.1703-1708: Rollas, S .; Kalyoncuoglu, N .; Sur-Altiner, D .; Yegenoglu, Y .; Pharmazie, 1993, Vol. 48, No. 4, p. 308-309.

(Reference Example 17)
[4- (4-Chlorophenyl) -5-methylthiazol-2-yl] amine
Leber, Steven V .; Scicinski, Jan J .; Scott, James S .; Smits, Rene; Thomas, Andrew W .; J. Chem. Soc. Perkin Trans. 1, 1999, Vol. 17, p.2425-2428; Wipf, Peter; Aslan, Diana C .; Southwick, Eileen C .; Lazo, John S .; Bioorg. Med. Chem. Lett., 2001, 11, 3, p. 313-318; Sen, AB; Roy, AK; J. Indian Chem. Soc .; 1960, Vol. 37, pp. 427-428.

(Reference Example 18)
2-Bromo-N- (4-ethoxyphenyl) propionamide p-phenetidine (27 mg, 0.20 mmol) was dissolved in N, N-dimethylformamide (1.5 ml) and 2-bromopropionic acid (46 mg, 0.30 mmol). ) And 1-hydroxy-7-azabenzotriazole (30 mg, 0.22 mmol) and stirred at room temperature for 10 minutes, then 1-ethyl-3- (dimethylaminopropyl) carbodiimide hydrochloride (58 mg, 0.30 mmol) was added. In addition, the mixture was stirred at 40 ° C. for 20 hours. The reaction mixture was diluted with ethyl acetate and washed with saturated aqueous sodium hydrogen carbonate. The organic layer was simply purified by silica gel filtration using ethyl acetate, and the solvent was concentrated under reduced pressure to obtain the title compound. This compound was used in the next reaction without purification.
MS (APCI, m / z): 272, 274 (M + H) ⁺ .
HPLC; Rt = 4.07min.

(Reference Example 19)
[4- [2- [N- (2,3-Dimethylphenyl) -N- (quinoline-8-sulfonyl) amino] acetylamino] phenoxy] acetic acid [N- (2,3-dimethyl (Phenyl) -N- (quinoline-8-sulfonyl) amino] acetic acid and the known compound (4-aminophenoxy) acetic acid (tert-butyl) ester shown in Reference Example 15 were used in the same manner as in Example 152. To give [4- [2- [N- (2,3-dimethylphenyl) -N- (quinoline-8-sulfonyl) amino] acetylamino] phenoxy] acetic acid (tert-butyl) ester. Reaction was conducted in the same manner as in 256 to give the title compound.
MS (APCI, m / z): 520 (M + H) ⁺ .
HPLC; Rt = 4.13min.

(Reference Example 20)
[N- (2-methoxypyridin-3-yl) -N- (naphthalene-1-sulfonyl) amino] acetic acid Naphthalene-1-sulfonic acid prepared in Reference Example 21 [N- (2-methoxypyridin-3-yl )] Amide was used in the same manner as in Reference Example 13 to obtain the title compound.
MS (APCI, m / z): 373 (M + H) ⁺ .
HPLC; Rt = 4.22min.

(Reference Example 21)
Naphthalene-1-sulfonic acid [N- (2-methoxypyridin-3-yl)] amide
Using 1-naphthalenesulfonyl chloride, the reaction was carried out in the same manner as in Reference Example 14 to obtain the title compound.
MS (APCI, m / z): 315 (M + H) ⁺ .
HPLC; Rt = 4.43min.

(Reference Example 22)
[N- (2,3-dimethylphenyl) -N- (4-fluoronaphthalene-1-sulfonyl) amino] acetic acid 4-fluoronaphthalene-1-sulfonic acid obtained in Reference Example 23 [N- (2,3 -Dimethylphenyl)] amide was used in the same manner as in Reference Example 1 to obtain the title compound.
MS (APCI, m / z): 388 (M + H) ⁺ .
HPLC; Rt = 5.18min.

(Reference Example 23)
4-Fluoronaphthalene-1-sulfonic acid [N- (2,3-dimethylphenyl)] amide
Using 4-fluoronaphthalene-1-sulfonyl chloride, the reaction was carried out in the same manner as in Reference Example 2 to obtain the title compound.
MS (APCI, m / z): 330 (M + H) ⁺ .
HPLC; Rt = 5.64min.

(Test Example 1)
(1) Preparation of DGAT1 According to a reported method, a microsomal fraction in which mouse DGAT1 was highly expressed was prepared as follows (Cases, S. et al., Proc. Natl. Acad. Sci. US A. 1998, 95, p.13018-13023). A cDNA encoding mouse DGAT1 was cloned from a mouse cDNA library by a polymerase chain reaction (hereinafter referred to as “PCR”) and introduced into an insect cell virus vector (baculovirus expression system, Invitrogen). Insect cells (High Five, Sf9, Sf21, etc., Invitrogen) are infected with the virus, and then the cells are buffered with A (0.1 M sucrose, 50 mM KCl, 40 mM potassium phosphate (pH 7.4), 30 mM EDTA, 1% Protease inhibitor cocktail (SIGMA, P-8340)] and crushed with a Polytron homogenizer. The supernatant obtained by subjecting the homogenate to low speed centrifugation (10,000 × g, 30 minutes) was further centrifuged at high speed (100,000 × g, 60 minutes), and the precipitate was resuspended in buffer A as a microsomal fraction, which was combined with DGAT1 enzyme. did. DGAT1 enzyme was divided into small volumes and stored at -80 ° C.
(2) DGAT1 inhibitory activity test Reaction solution [175 mM Tris-HCl (pH 8.0), 8 mM MgCl ₂ , 1 mg / ml BSA, 0.5 mM 1,2-dioleoyl-sn-glycerol (10-fold concentration] 10% EtOH solution), 30 μM [ ¹⁴ C] -oleoyl-CoA (about 50 mCi / mmol), 0.5% triton X-100, DGAT1 enzyme (10 μg) obtained in Test Example 1 (1), test compound Or a vehicle (DMSO / MeOH, 7: 3 solution, 5% added), total volume 50 μl] was incubated at room temperature (23 ° C.) for 30 minutes. To the reaction mixture was added a reaction stop solution (70 μl) consisting of isopropanol / 1-heptane / water (80: 20: 2, v / v / v) and stirred, then water (30 μl) and 1-heptane (100 μl) Was added and stirred. A 1-heptane layer (50 μl) was spotted on a TLC plate and developed with a developing solvent consisting of 1-hexane / diethyl ether / acetic acid (85: 15: 1, v / v / v). The radioactivity of the triglyceride fraction was quantified using a BAS2000 bioimage analyzer (Fuji Film), and the inhibitory activity of the test compound was calculated by the following formula by comparing with the control. The unreacted (0 minute incubation) radioactivity was used as the background.

Inhibition rate = 100 − [(radioactivity at the time of addition of test compound) − (background)] / [(radioactivity of control) − (background)] × 100

Examples 1, 15, 18, 20, 21, 27, 28, 29, 30, 32, 34, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 51, 53, 54, 55, 56, 57, 58, 61, 64, 65, 66, 67, 68, 78, 79, 85, 100, 109, 110, 111, 113, 114, 117, 122, 126, 143, 169, 177, 178, 179, 180, 192, 196, 198, 200, 203, 212, 215, 230, 231, 233, 234, 237, 240, 242, 243, 244, 245, 247, 249, 250, 251, 253, 255, 257, 258, 259, 260, 261, 283, 285, 286, 290, 292, 293, 295, 296, 301, 302, 303, 308, 09, 315, 316, 320, 322, 323, 325, 326, 328, 329, 330, 333, 338, 340, 341, 342, 343, 344, 345, 346, 348, 349, 350, 351, 357, Compounds 359, 367, 369, 370, 371, 372, 373, 374, 375, and 376 showed an inhibition rate of 40% or more at a test compound concentration of 1 μg / ml.
From the above results, the compound of the present invention has an excellent DGAT inhibitory action and is effective in obesity, obesity, hyperlipidemia, hyperTGemia, dyslipidemia, diabetes, arteriosclerosis, or obesity. It is useful as a therapeutic or prophylactic agent for the resulting hyperlipidemia, hyperTGemia, dyslipidemia, diabetes, arteriosclerosis, or hypertension.
The DGAT inhibitory activity test is not limited to the above method, and for example, microsomes prepared from the small intestine, adipose tissue or liver of animals such as rats and mice may be used as the DGAT enzyme. Alternatively, microsomes prepared from cultured cells (3T3-L1 adipocytes, primary cultured adipocytes, Caco2 cells, HepG2 cells, etc.) or cultured cells highly expressing DGAT can also be used as the DGAT enzyme. Further, in order to efficiently evaluate a large number of test compounds in a short time, a flash plate (PerkinElmer) in which the extraction operation is omitted can be used.

The compound having the general formula (I) or the general formula (Ia) of the present invention or a pharmacologically acceptable salt thereof has an excellent DGAT inhibitory action, and is used for warm-blooded animals (particularly humans). Disease, hyperlipidemia, hyperTGemia, dyslipidemia, insulin resistance syndrome, impaired glucose tolerance, diabetes, diabetic complications (diabetic peripheral neuropathy, diabetic nephropathy, diabetic retinopathy, diabetic Macrovascular disease etc.), cataract, gestational diabetes, polycystic ovary syndrome, arteriosclerosis (including arteriosclerosis caused by the diseases shown above and below), atherosclerosis, diabetic arteriosclerosis, Or obesity-related hyperlipidemia, hyperTG, dyslipidemia, insulin resistance syndrome, impaired glucose tolerance, diabetes, diabetic complications (diabetic peripheral neuropathy, diabetic nephropathy, diabetic retina , Including diabetic macroangiopathy , Cataract, gestational diabetes, polycystic ovary syndrome, arteriosclerosis (including arteriosclerosis due to the diseases shown above and below), atherosclerosis, diabetic arteriosclerosis, hypertension, cerebrovascular disorder, Coronary artery disease, fatty liver, respiratory abnormalities, low back pain, knee osteoarthritis, gout, or cholelithiasis, preferably obesity, obesity, hyperlipidemia, hyperTGemia, dyslipidemia, diabetes, Arteriosclerosis or hyperlipidemia due to obesity, hyperTGemia, dyslipidemia, diabetes, arteriosclerosis or hypertension, more preferably obesity, obesity, hyperlipidemia It is useful as a therapeutic agent or prophylactic agent (especially a therapeutic agent) for hyperTGemia, diabetes, or arteriosclerosis.

Claims (20)

Formula (I)

[Wherein, A ¹ is an optionally substituted C ₁ -C ₈ alkyl group (the substituents are the same or different and each represent 1 to 3 groups selected from substituent group α),
An optionally substituted phenyl- (C ₁ -C ₆ alkyl) group (the substituents are the same or different and represent 1 to 3 groups selected from substituent group α);
An optionally substituted phenoxy- (C ₁ -C ₆ alkyl) group (the substituents may be the same or different and each represent 1 to 3 groups selected from substituent group α);
An optionally substituted phenoxyphenyl- (C ₁ -C ₆ alkyl) group (the substituents are the same or different and each represent 1 to 3 groups selected from substituent group α);
A C ₃ -C ₈ cycloalkyl group which may be substituted (the substituents are the same or different and represent 1 to 3 groups selected from the substituent group α),
A phenyl group which may be substituted (the substituents are the same or different and represent 1 to 3 groups selected from substituent group α);
A substituted phenyl group [the substituent is an essential phenyl group which may be substituted (the substituents are the same or different and represent 1 to 3 groups selected from the substituent group α)] And optionally represents the same or different and 1 to 2 groups selected from the substituent group α],
A substituted phenyl group [the substituent is, as essential, a 4- to 8-membered group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom, which may be substituted] A heterocyclyl group (the substituents are the same or different and represent 1 to 3 groups selected from the substituent group α), and are optionally the same or different and selected from the substituent group α; To 2 groups]
An optionally substituted phenoxyphenyl group (the substituents are the same or different and represent 1 to 3 groups selected from substituent group α),
A benzoylphenyl group which may be substituted (the substituents are the same or different and represent 1 to 3 groups selected from substituent group α);
A naphthyl group which may be substituted (the substituents are the same or different and represent 1 to 3 groups selected from substituent group α),
An indanyl, indenyl, tetrahydronaphthyl, or dihydronaphthyl group which may be substituted (the substituents are the same or different and represent 1 to 3 groups selected from the substituent group α);
A 4- to 8-membered heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom, which may be substituted (the substituents may be the same or different, and the substituent group α 1 to 3 groups selected from
A substituted 5- to 6-membered aromatic heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom [the substituent is substituted as an essential one; Or a phenyl group (the substituents are the same or different and represent 1 to 3 groups selected from the substituent group α), and are optionally the same or different and selected from the substituent group α. 1 to 2 groups]
A substituted 5- to 6-membered aromatic heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom [the substituent is substituted as an essential one; A 4- to 8-membered heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom (the substituents may be the same or different and selected from the substituent group α) And optionally represents the same or different and 1 to 2 groups selected from the substituent group α], or
An optionally substituted 8- to 10-membered aromatic heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom (the substituents may be the same or different, 1 to 3 groups selected from group α)
A ² is an optionally substituted C ₁ -C ₈ alkyl group (the substituents are the same or different and each represent 1 to 3 groups selected from the substituent group β);
Di (C ₁ -C ₆ alkyl) amino- (C ₁ -C ₆ alkyl) group which may be substituted (the substituent is the same or different and represents 1 to 3 groups selected from substituent group β) Show),
(C ₁ -C ₆ alkylthio)-(C ₁ -C ₆ alkyl) group which may be substituted (the substituent is the same or different and represents 1 to 3 groups selected from substituent group β) ,
An optionally substituted phenyl- (C ₁ -C ₆ alkyl) group (the substituents are the same or different and represent 1 to 3 groups selected from substituent group β),
An optionally substituted (4- to 8-membered heterocyclyl containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom)-(C ₁ -C ₆ alkyl) group (the substituent Are the same or different and represent 1 to 3 groups selected from the substituent group β),
An optionally substituted phenoxy- (C ₁ -C ₆ alkyl) group (the substituents are the same or different and represent 1 to 3 groups selected from substituent group β),
A C ₃ -C ₈ cycloalkyl group which may be substituted (the substituents are the same or different and represent 1 to 3 groups selected from substituent group β),
A phenyl group which may be substituted (the substituents are the same or different and represent 1 to 3 groups selected from the substituent group β);
A substituted phenyl group [the substituent is an optionally substituted phenyl group (the substituent is the same or different and represents 1 to 3 groups selected from the substituent group β)] And optionally represents the same or different and 1 to 2 groups selected from the substituent group β],
A substituted phenyl group [the substituent is, as essential, a 4- to 8-membered group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom, which may be substituted] 1 represents a heterocyclyl group (the substituents are the same or different and represent 1 to 3 groups selected from the substituent group β), and are optionally the same or different and selected from the substituent group β. To 2 groups]
An optionally substituted naphthyl group (the substituents are the same or different and represent 1 to 3 groups selected from substituent group β),
Optionally substituted indanyl, indenyl, tetrahydronaphthyl, or dihydronaphthyl group (the substituents are the same or different and represent 1 to 3 groups selected from substituent group β),
Optionally substituted 5- to 6-membered aromatic heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom (the substituents may be the same or different, 1 to 3 groups selected from group β)
A substituted 5- to 6-membered aromatic heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom [the substituent is substituted as an essential one; Or a phenyl group (the substituents are the same or different and represent 1 to 3 groups selected from the substituent group β), and are optionally the same or different and selected from the substituent group β. 1 to 2 groups]
A substituted 5- to 6-membered aromatic heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom [the substituent is substituted as an essential one; A 4- to 8-membered heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom (the substituents are the same or different and are selected from the substituent group β) And optionally represents the same or different and 1 to 2 groups selected from the substituent group β], or
An optionally substituted 8- to 10-membered aromatic heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom (the substituents may be the same or different, Represents 1 to 3 groups selected from group β);
A ³ is an optionally substituted phenyl- (C ₁ -C ₆ alkyl) group (the substituents are the same or different and each represent 1 to 3 groups selected from substituent group β);
An optionally substituted naphthylmethyl group (the substituents are the same or different and represent 1 to 3 groups selected from substituent group β),
A phenyl group which may be substituted (the substituents are the same or different and represent 1 to 3 groups selected from the substituent group β);
A substituted phenyl group [the substituent is an optionally substituted phenyl group (the substituent is the same or different and represents 1 to 3 groups selected from the substituent group β)] And optionally represents the same or different and 1 to 2 groups selected from the substituent group β],
A substituted phenyl group [the substituent is, as essential, a 4- to 8-membered group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom, which may be substituted] 1 represents a heterocyclyl group (the substituents are the same or different and represent 1 to 3 groups selected from the substituent group β), and are optionally the same or different and selected from the substituent group β. To 2 groups]
An optionally substituted naphthyl group (the substituents are the same or different and represent 1 to 3 groups selected from substituent group β),
Optionally substituted 5- to 6-membered aromatic heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom (the substituents may be the same or different, 1 to 3 groups selected from group β)
A substituted 5- to 6-membered aromatic heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom [the substituent is substituted as an essential one; Or a phenyl group (the substituents are the same or different and represent 1 to 3 groups selected from the substituent group β), and are optionally the same or different and selected from the substituent group β. 1 to 2 groups]
A substituted 5- to 6-membered aromatic heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom [the substituent is substituted as an essential one; A 4- to 8-membered heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom (the substituents are the same or different and are selected from the substituent group β) And optionally represents the same or different and 1 to 2 groups selected from the substituent group β], or
An optionally substituted 8- to 10-membered aromatic heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom (the substituents may be the same or different, Represents 1 to 3 groups selected from group β);
R ¹ represents a group having the formula —NHCO—, —NR ^1b CO— (R ^1b represents a C ₁ -C ₆ alkyl group) or —CO—;
R ² represents a hydrogen atom or a C ₁ -C ₆ alkyl group;
Substituent group α is C ₁ -C ₆ alkyl, halogeno C ₁ -C ₆ alkyl, hydroxy C ₁ -C ₆ alkyl, aminosulfonyl C ₁ -C ₆ alkyl, (C ₁ -C ₆ alkyl) aminosulfonyl- ( C ₁ -C ₆ alkyl), hydroxyimino C ₁ -C ₆ alkyl, (C ₁ -C ₆ alkoxyimino) - (C ₁ -C ₆ alkyl), C ₃ -C ₈ cycloalkyl, C ₂ -C ₆ alkynyl , hydroxy, C ₁ -C ₆ alkoxy, halogeno C ₁ -C ₆ alkoxy, formyloxy, C ₂ -C ₇ alkylcarbonyloxy, C ₁ -C ₆ alkylthio, C ₁ -C ₆ alkylsulfinyl, C ₁ -C ₆ alkylsulfonyl, aminosulfonyl, (C ₁ -C ₆ alkyl) aminosulfonyl, amino, C ₁ -C ₆ alkylamino, di (C ₁ -C ₆ alkyl) amino (said alkyl groups may be the same or different ), Formylamino, C ₂ -C ₇ alkylcarbonylamino, C ₂ -C ₇ alkoxycarbonylamino, C ₁ -C ₆ alkylsulfonylamino, formyl, C ₂ -C ₇ alkylcarbonyl, carboxy, C ₂ -C ₇ alkoxy carbonyl, carbamoyl, C ₂ -C ₇ alkylaminocarbonyl, di (C ₁ -C ₆ alkyl) aminocarbonyl (the alkyl group, the same or different), a group having a cyano, nitro, halogeno, equation -OCH ₂ COR ³ [Wherein R ³ represents hydroxy, C ₁ -C ₆ alkoxy, amino, C ₁ -C ₆ alkylamino, or di (C ₁ -C ₆ alkyl) amino (the alkyl groups are the same or different). A group having the formula —CH ₂ COOR ⁴ , wherein R ⁴ represents a hydrogen atom or C ₁ -C ₆ alkyl, and a C ₁ -C ₄ alkyl Indicates a group consisting of a rangeoxy group;
Substituent group β is C ₁ -C ₆ alkyl, halogeno C ₁ -C ₆ alkyl, C ₃ -C ₈ cycloalkyl, hydroxy, C ₁ -C ₆ alkoxy, halogeno C ₁ -C ₆ alkoxy, formyloxy, C ₂ -C ₇ alkylcarbonyloxy, C ₁ -C ₆ alkylthio, C ₁ -C ₆ alkylsulfinyl, C ₁ -C ₆ alkylsulfonyl, amino, C ₁ -C ₆ alkylamino, di (C ₁ -C ₆ alkyl) amino (said alkyl groups may be the same or different), formylamino, C ₂ -C ₇ alkylcarbonylamino, C ₂ -C ₇ alkoxycarbonylamino, formyl, C ₂ -C ₇ alkylcarbonyl, carboxy, C ₂ -C ₇ Alkoxycarbonyl, carbamoyl, C ₂ -C ₇ alkylaminocarbonyl, di (C ₁ -C ₆ alkyl) aminocarbonyl (the alkyl groups are the same Or cyano, nitro, halogeno, a group having the formula —CH ₂ COOR ⁴ (wherein R ⁴ represents a hydrogen atom or C ₁ -C ₆ alkyl), and C ₁ -C ₄ alkylenedi A group consisting of an oxy group is shown. ] An acyl coenzyme A: diacylglycerol acyltransferase inhibitor comprising a sulfonamide compound having a pharmaceutically acceptable salt or a pharmacologically acceptable salt thereof as an active ingredient.
General formula (Ia)

[ ^Wherein , A ^1a represents an optionally substituted phenyl group (the substituents are the same or different and represent 1 to 3 groups selected from substituent group α),
A substituted phenyl group [the substituent is an essential phenyl group which may be substituted (the substituents are the same or different and represent 1 to 3 groups selected from the substituent group α)] And optionally represents the same or different and 1 to 2 groups selected from the substituent group α],
A substituted phenyl group [the substituent is, as essential, a 4- to 8-membered group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom, which may be substituted] A heterocyclyl group (the substituents are the same or different and represent 1 to 3 groups selected from the substituent group α), and are optionally the same or different and selected from the substituent group α; To 2 groups]
A 5- to 6-membered aromatic heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom, which may be substituted (the substituents may be the same or different, 1 to 3 groups selected from group α)
A substituted 5- to 6-membered aromatic heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom [the substituent is substituted as essential Or a phenyl group (the substituents are the same or different and represent 1 to 3 groups selected from the substituent group α), and are optionally the same or different and selected from the substituent group α. 1 or 2 groups], or
A substituted 5- to 6-membered aromatic heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom [the substituent is substituted as essential A 4- to 8-membered heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom (the substituents may be the same or different and selected from the substituent group α) And optionally represents the same or different and 1 to 2 groups selected from the substituent group α];
A ^2a represents a phenyl group which may be substituted (the substituents are the same or different and each represent 1 to 3 groups selected from the substituent group β);
A substituted phenyl group [the substituent is an optionally substituted phenyl group (the substituent is the same or different and represents 1 to 3 groups selected from the substituent group β)] And optionally represents the same or different and 1 to 2 groups selected from the substituent group β],
A substituted phenyl group [the substituent is, as essential, a 4- to 8-membered heterocyclyl having 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom] A group (the substituents are the same or different and represent 1 to 3 groups selected from the substituent group β), and optionally are the same or different and are selected from the substituent group β 2 groups are shown]
An optionally substituted naphthyl group (the substituents are the same or different and represent 1 to 3 groups selected from substituent group β),
Optionally substituted 5- to 6-membered aromatic heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom (the substituents may be the same or different, 1 to 3 groups selected from group β)
A substituted 5- to 6-membered aromatic heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom [the substituent is substituted as an essential one; Or a phenyl group (the substituents are the same or different and represent 1 to 3 groups selected from the substituent group β), and are optionally the same or different and selected from the substituent group β. 1 to 2 groups]
A substituted 5- to 6-membered aromatic heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom [the substituent is substituted as an essential one; A 4- to 8-membered heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom (the substituents are the same or different and are selected from the substituent group β) And optionally represents the same or different and 1 to 2 groups selected from the substituent group β], or
An optionally substituted 8- to 10-membered aromatic heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom (the substituents may be the same or different, Represents 1 to 3 groups selected from group β);
A ^3a represents a substituted phenyl group [the substituent is an essential phenyl group which may be substituted (the substituents may be the same or different and each may have 1 to 3 substituents selected from the substituent group β]; And optionally represents one or two groups selected from the same or different, substituent group β],
A substituted phenyl group [the substituent is, as essential, a 4- to 8-membered group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom, which may be substituted] 1 represents a heterocyclyl group (the substituents are the same or different and represent 1 to 3 groups selected from the substituent group β), and are optionally the same or different and selected from the substituent group β. To 2 groups]
An optionally substituted naphthyl group (the substituents are the same or different and represent 1 to 3 groups selected from substituent group β),
A substituted 5- to 6-membered aromatic heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom [the substituent is substituted as an essential one; Or a phenyl group (the substituents are the same or different and represent 1 to 3 groups selected from the substituent group β), and are optionally the same or different and selected from the substituent group β. 1 to 2 groups]
A substituted 5- to 6-membered aromatic heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom [the substituent is substituted as an essential one; A 4- to 8-membered heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom (the substituents are the same or different and are selected from the substituent group β) And optionally represents the same or different and 1 to 2 groups selected from the substituent group β], or
An optionally substituted 8- to 10-membered aromatic heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom (the substituents may be the same or different, Represents 1 to 3 groups selected from group β);
R ^1a represents a group having the formula —NHCO— or —CO—;
Substituent group α is C ₁ -C ₆ alkyl, halogeno C ₁ -C ₆ alkyl, hydroxy C ₁ -C ₆ alkyl, aminosulfonyl C ₁ -C ₆ alkyl, (C ₁ -C ₆ alkyl) aminosulfonyl- ( C ₁ -C ₆ alkyl), hydroxyimino C ₁ -C ₆ alkyl, (C ₁ -C ₆ alkoxyimino) - (C ₁ -C ₆ alkyl), C ₃ -C ₈ cycloalkyl, C ₂ -C ₆ alkynyl , hydroxy, C ₁ -C ₆ alkoxy, halogeno C ₁ -C ₆ alkoxy, formyloxy, C ₂ -C ₇ alkylcarbonyloxy, C ₁ -C ₆ alkylthio, C ₁ -C ₆ alkylsulfinyl, C ₁ -C ₆ alkylsulfonyl, aminosulfonyl, (C ₁ -C ₆ alkyl) aminosulfonyl, amino, C ₁ -C ₆ alkylamino, di (C ₁ -C ₆ alkyl) amino (said alkyl groups may be the same or different ), Formylamino, C ₂ -C ₇ alkylcarbonylamino, C ₂ -C ₇ alkoxycarbonylamino, C ₁ -C ₆ alkylsulfonylamino, formyl, C ₂ -C ₇ alkylcarbonyl, carboxy, C ₂ -C ₇ alkoxy carbonyl, carbamoyl, C ₂ -C ₇ alkylaminocarbonyl, di (C ₁ -C ₆ alkyl) aminocarbonyl (the alkyl group, the same or different), a group having a cyano, nitro, halogeno, equation -OCH ₂ COR ³ [Wherein R ³ represents hydroxy, C ₁ -C ₆ alkoxy, amino, C ₁ -C ₆ alkylamino, or di (C ₁ -C ₆ alkyl) amino (the alkyl groups are the same or different). A group having the formula —CH ₂ COOR ⁴ , wherein R ⁴ represents a hydrogen atom or C ₁ -C ₆ alkyl, and a C ₁ -C ₄ alkyl Indicates a group consisting of a rangeoxy group;
Substituent group β is C ₁ -C ₆ alkyl, halogeno C ₁ -C ₆ alkyl, C ₃ -C ₈ cycloalkyl, hydroxy, C ₁ -C ₆ alkoxy, halogeno C ₁ -C ₆ alkoxy, formyloxy, C ₂ -C ₇ alkylcarbonyloxy, C ₁ -C ₆ alkylthio, C ₁ -C ₆ alkylsulfinyl, C ₁ -C ₆ alkylsulfonyl, amino, C ₁ -C ₆ alkylamino, di (C ₁ -C ₆ alkyl) amino (said alkyl groups may be the same or different), formylamino, C ₂ -C ₇ alkylcarbonylamino, C ₂ -C ₇ alkoxycarbonylamino, formyl, C ₂ -C ₇ alkylcarbonyl, carboxy, C ₂ -C ₇ Alkoxycarbonyl, carbamoyl, C ₂ -C ₇ alkylaminocarbonyl, di (C ₁ -C ₆ alkyl) aminocarbonyl (the alkyl groups are the same Or cyano, nitro, halogeno, a group having the formula —CH ₂ COOR ⁴ (wherein R ⁴ represents a hydrogen atom or C ₁ -C ₆ alkyl), and C ₁ -C ₄ alkylenedi A group consisting of an oxy group is shown. However, the case where A ^1a is a 4- (thiazol-4-yl) phenyl group which may be substituted is excluded. Or a pharmacologically acceptable salt thereof.
A ^1a may be a phenyl group which may be substituted (the substituents are the same or different and represent 1 to 3 groups selected from the substituent group α);
A substituted phenyl group [the substituent is, as essential, a 4- to 8-membered group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom, which may be substituted] A heterocyclyl group (the substituents are the same or different and represent 1 to 3 groups selected from the substituent group α), and are optionally the same or different and selected from the substituent group α; To 2 groups]
Optionally substituted 5- to 6-membered aromatic heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom (the substituents may be the same or different, 1 to 3 groups selected from group α), or
A substituted 5- to 6-membered aromatic heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom [the substituent is substituted as essential A 4- to 8-membered heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom (the substituents may be the same or different and selected from the substituent group α) And optionally represents the same or different and 1 to 2 groups selected from the substituent group α]. The sulfonamide according to claim 2 Compound or pharmacologically acceptable salt thereof.
A ^1a may be substituted, phenyl, thiazolyl, isothiazolyl, or pyridyl group (the substituents are the same or different and represent 1 to 2 groups selected from substituent group α1), or A substituted phenyl, thiazolyl, isothiazolyl or pyridyl group [the substituent is, as an essential one, one to four selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom; A 5- to 7-membered heterocyclyl group containing the following atoms (the substituents are the same or different and represent 1 to 2 groups selected from the substituent group α1), and the optional substituent group α1 Represents one group selected from]
Substituent group α1 is C ₁ -C ₄ alkyl, halogeno C ₁ -C ₄ alkyl, hydroxy C ₁ -C ₄ alkyl, hydroxyimino C ₁ -C ₄ alkyl, (C ₁ -C ₄ alkoxyimino)-(C ₁ -C ₄ alkyl), C ₃ -C ₆ cycloalkyl, C ₂ -C ₄ alkynyl, C ₁ -C ₄ alkoxy, halogeno C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ alkyl sulfinyl, C ₁ -C ₄ alkylsulfonyl, C ₁ -C ₄ alkylamino, di (C ₁ -C ₄ alkyl) amino (said alkyl groups may be the same or different), formyl, C ₂ -C ₅ alkylcarbonyl, C ₂ -C ₅ alkoxycarbonyl, carbamoyl, C ₂ -C ₅ alkylaminocarbonyl, di (C ₁ -C ₄ alkyl) aminocarbonyl (the alkyl group, the same or different), cyano, nitro Fluoro, chloro, bromo, group [wherein having the formula -OCH ₂ COR ^3a, R ^3a is, C ₁ -C ₄ alkoxy, amino, C ₁ -C ₄ alkylamino, di (C ₁ -C ₄ alkyl) amino (The alkyl groups are the same or different), or a group having the formula —CH ₂ COOR ^4a (wherein R ^4a represents C ₁ -C ₄ alkyl) and C ₁ -C ₃ alkylenedioxy The sulfonamide compound or a pharmacologically acceptable salt thereof according to claim 2, which is a group consisting of groups.
A ^1a is a substituted phenyl group [the substituent is, as an essential component, optionally containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom, and a sulfur atom. A 5- to 6-membered aromatic heterocyclyl group (the substituents are the same or different and represent 1 to 2 groups selected from the substituent group α2), and are optionally selected from the substituent group α2 Shows one group]
Substituent group α2 is C ₁ -C ₄ alkyl, halogeno C ₁ -C ₄ alkyl, hydroxymethyl, hydroxyethyl, hydroxyiminomethyl, hydroxyiminoethyl, methoxyiminomethyl, ethoxyiminomethyl, methoxyiminoethyl, ethoxyiminoethyl. , Ethynyl, propynyl, C ₁ -C ₄ alkoxy, halogeno C ₁ -C ₄ alkoxy, methylthio, ethylthio, C ₁ -C ₄ alkylamino, di (C ₁ -C ₄ alkyl) amino (the alkyl groups are the same or Different), formyl, C ₂ -C ₅ alkylcarbonyl, methoxycarbonyl, ethoxycarbonyl, carbamoyl, methylaminocarbonyl, ethylaminocarbonyl, di (C ₁ -C ₄ alkyl) aminocarbonyl (the alkyl groups are the same or different) , Cyano, nitro, fluoro, Chloro, bromo, a group having the formula —OCH ₂ COR ^3b [wherein R ^3b is methoxy, ethoxy, amino, C ₁ -C ₄ alkylamino, or di (C ₁ -C ₄ alkyl) amino (the alkyl The groups may be the same or different)], a group having the formula —CH ₂ COOR ^4b (R ^4b represents methyl or ethyl), and a group consisting of a C ₁ -C ₃ alkylenedioxy group Or a pharmacologically acceptable salt thereof.
A ^1a is a substituted phenyl group [this substituent is optionally substituted, pyrrolyl, pyrazolyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, triazolyl, or tetrazolyl group (The substituents are the same or different and represent one or two groups selected from the substituent group α3), and optionally, one group selected from the substituent group α3] And
Substituent group α3 is methyl, ethyl, fluoromethyl, chloromethyl, difluoromethyl, trifluoromethyl, pentafluoroethyl, fluoromethoxy, chloromethoxy, difluoromethoxy, trifluoromethoxy, pentafluoroethoxy, methoxy, ethoxy, methylamino , Ethylamino, dimethylamino, diethylamino, methylcarbonyl, ethylcarbonyl, dimethylaminocarbonyl, diethylaminocarbonyl, cyano, nitro, fluoro, chloro, and a group having the formula —OCH ₂ COR ^3c where R ^3c is amino Or a sulfonamide compound according to claim 2, which is a group consisting of methylenedioxy and ethylenedioxy groups. A pharmacologically acceptable salt thereof.
A ^2a is a phenyl group which may be substituted (the substituents are the same or different and each represent 1 to 3 groups selected from substituent group β);
An optionally substituted naphthyl group (the substituents are the same or different and represent 1 to 3 groups selected from substituent group β),
Optionally substituted 5- to 6-membered aromatic heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom (the substituents may be the same or different, 1 to 3 groups selected from group β), or
An optionally substituted 8- to 10-membered aromatic heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom (the substituents may be the same or different, The sulfonamide compound or a pharmacologically acceptable salt thereof according to any one of claims 2 to 6, which represents 1 to 3 groups selected from group β.
A ^2a is a phenyl group which may be substituted (the substituents are the same or different and each represents 1 to 2 groups selected from the substituent group β1), or
A 5- to 6-membered aromatic heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom which may be substituted (the heterocyclyl group is one or more nitrogen atoms) And may contain an oxygen atom and a sulfur atom, and the substituents are the same or different and represent 1 to 2 groups selected from the substituent group β1),
Substituent group β1 is C ₁ -C ₄ alkyl, halogeno C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, halogeno C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ alkylsulfinyl. C ₁ -C ₄ alkylsulfonyl, amino, C ₁ -C ₄ alkylamino, di (C ₁ -C ₄ alkyl) amino (the alkyl groups are the same or different), formyl, C ₂ -C ₅ alkylcarbonyl, C ₂ -C ₅ alkoxycarbonyl, carbamoyl, C ₂ -C ₅ aminocarbonyl, di (C ₁ -C ₄ alkyl) aminocarbonyl (the alkyl group, the same or different), cyano, nitro, fluoro, chloro, bromo, and, sulfonamide compound or a pharmacologically acceptable salt thereof according to any one of claims 2 to 6 is the group consisting of C ₁ -C ₃ alkylenedioxy group.
A ^2a is an optionally substituted phenyl or pyridyl group (the substituents are the same or different and represent 1 to 2 groups selected from the substituent group β2);
Substituent group β2 is C ₁ -C ₄ alkyl, halogeno C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, fluoromethoxy, chloromethoxy, difluoromethoxy, trifluoromethoxy, pentafluoroethoxy, methylthio, ethylthio, methyl Sulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, methylamino, ethylamino, dimethylamino, diethylamino, formyl, methylcarbonyl, ethylcarbonyl, methoxycarbonyl, ethoxycarbonyl, carbamoyl, methylaminocarbonyl, ethylaminocarbonyl, dimethylaminocarbonyl, The group according to any one of claims 2 to 6, which is a group consisting of diethylaminocarbonyl, cyano, nitro, fluoro, chloro, bromo, methylenedioxy, and ethylenedioxy groups Crab according sulfonamide compound or a pharmacologically acceptable salt thereof.
A ^2a is a phenyl group which may be substituted (the substituents are the same or different and represent 1 to 2 groups selected from the substituent group β3);
The substituent group β3 is a group consisting of methyl, ethyl, fluoromethyl, chloromethyl, difluoromethyl, trifluoromethyl, pentafluoroethyl, methoxy, ethoxy, fluoro, and a chloro group. Or a pharmacologically acceptable salt thereof.
A ^3a is an optionally substituted naphthyl group (the substituents are the same or different and each represent 1 to 3 groups selected from the substituent group β), or a nitrogen atom, which may be substituted, 8- to 10-membered aromatic heterocyclyl group containing 1 to 4 atoms selected from the group consisting of oxygen atom and sulfur atom (the substituents are the same or different, and 1 to 3 selected from substituent group β) The sulfonamide compound according to any one of claims 2 to 10 or a pharmacologically acceptable salt thereof.
A ^3a is a naphthyl group which may be substituted (the substituents are the same or different and represent 1 or 2 groups selected from substituent group β1), or a nitrogen atom which may be substituted; 9 to 10-membered aromatic heterocyclyl group containing 1 to 4 atoms selected from the group consisting of oxygen atom and sulfur atom (the heterocyclyl group contains one or more nitrogen atoms, oxygen atom and sulfur atom The sulfonamide compound according to any one of claims 2 to 10, wherein the substituent is the same or different and represents 1 to 2 groups selected from the substituent group β1). Or a pharmacologically acceptable salt thereof.
A ^3a is an optionally substituted naphthyl, quinolyl, isoquinolyl, quinazolinyl, or quinoxalinyl group (the substituents are the same or different and each represent one or two groups selected from substituent group β4) Yes,
Substituent group β4 is C ₁ -C ₄ alkyl, halogeno C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, fluoromethoxy, chloromethoxy, difluoromethoxy, trifluoromethoxy, pentafluoroethoxy, methylthio, ethylthio, methyl sulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, amino, C ₁ -C ₄ alkylamino, di (C ₁ -C ₄ alkyl) amino (said alkyl groups may be the same or different), formyl, methylcarbonyl, ethylcarbonyl, Methoxycarbonyl, ethoxycarbonyl, carbamoyl, methylaminocarbonyl, ethylaminocarbonyl, dimethylaminocarbonyl, diethylaminocarbonyl, cyano, nitro, fluoro, chloro, bromo, methylenedioxy, and ethylene dioxide Sulfonamide compound or a pharmacologically acceptable salt thereof according to any one of claims 2 to 10 is a group consisting of groups.
A ^3a is an optionally substituted naphthyl or quinolyl group (the substituents are the same or different and each represent one or two groups selected from substituent group β5);
Substituent group β5 consists of methyl, ethyl, fluoromethyl, chloromethyl, difluoromethyl, trifluoromethyl, pentafluoroethyl, methoxy, ethoxy, methylamino, ethylamino, dimethylamino, diethylamino, fluoro, and chloro groups The sulfonamide compound or a pharmacologically acceptable salt thereof according to any one of claims 2 to 10, which is a group.
The sulfonamide compound or a pharmacologically acceptable salt thereof according to any one of claims 2 to 14, wherein R ¹ is a group having the formula -NHCO-.
A ^1a may be a phenyl group which may be substituted (the substituents are the same or different and represent 1 to 3 groups selected from the substituent group α);
A substituted phenyl group [the substituent is an essential phenyl group which may be substituted (the substituents are the same or different and represent 1 to 3 groups selected from the substituent group α)] And optionally represents the same or different and 1 to 2 groups selected from the substituent group α],
A substituted phenyl group [the substituent is, as essential, a 4- to 8-membered group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom, which may be substituted] A heterocyclyl group (the substituents are the same or different and represent 1 to 3 groups selected from the substituent group α), and are optionally the same or different and selected from the substituent group α; To 2 groups]
A 5- to 6-membered aromatic heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom, which may be substituted (the substituents may be the same or different, 1 to 3 groups selected from group α)
A substituted 5- to 6-membered aromatic heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom [the substituent is substituted as essential Or a phenyl group (the substituents are the same or different and represent 1 to 3 groups selected from the substituent group α), and are optionally the same or different and selected from the substituent group α. 1 or 2 groups], or
A substituted 5- to 6-membered aromatic heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom [the substituent is substituted as an essential one; A 4- to 8-membered heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom (the substituents may be the same or different and selected from the substituent group α) And optionally represents the same or different and 1 to 2 groups selected from the substituent group α];
A ^2a is a phenyl group which may be substituted (the substituents are the same or different and each represent 1 to 3 groups selected from substituent group β);
A substituted phenyl group [the substituent is an optionally substituted phenyl group (the substituent is the same or different and represents 1 to 3 groups selected from the substituent group β)] And optionally represents the same or different and 1 to 2 groups selected from the substituent group β],
A substituted phenyl group [the substituent is, as essential, a 4- to 8-membered heterocyclyl having 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom] A group (the substituents are the same or different and represent 1 to 3 groups selected from the substituent group β), and optionally are the same or different and are selected from the substituent group β 2 groups are shown]
An optionally substituted naphthyl group (the substituents are the same or different and represent 1 to 3 groups selected from substituent group β),
Optionally substituted 5- to 6-membered aromatic heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom (the substituents may be the same or different, 1 to 3 groups selected from group β)
A substituted 5- to 6-membered aromatic heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom [the substituent is substituted as an essential one; Or a phenyl group (the substituents are the same or different and represent 1 to 3 groups selected from the substituent group β), and are optionally the same or different and selected from the substituent group β. 1 to 2 groups]
A substituted 5- to 6-membered aromatic heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom [the substituent is substituted as an essential one; A 4- to 8-membered heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom (the substituents are the same or different and are selected from the substituent group β) And optionally represents the same or different and 1 to 2 groups selected from the substituent group β], or
An optionally substituted 8- to 10-membered aromatic heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom (the substituents may be the same or different, 1 to 3 groups selected from group β)
A ^3a is a substituted phenyl group [the substituent is an essential phenyl group which may be substituted (the substituents may be the same or different, and 1 to 3 substituents selected from the substituent group β] And optionally represents the same or different one or two groups selected from the substituent group β],
A substituted phenyl group [the substituent is, as essential, a 4- to 8-membered group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom, which may be substituted] 1 represents a heterocyclyl group (the substituents are the same or different and represent 1 to 3 groups selected from the substituent group β), and are optionally the same or different and selected from the substituent group β. To 2 groups]
An optionally substituted naphthyl group (the substituents are the same or different and represent 1 to 3 groups selected from substituent group β),
A substituted 5- to 6-membered aromatic heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom [the substituent is substituted as an essential one; Or a phenyl group (the substituents are the same or different and represent 1 to 3 groups selected from the substituent group β), and are optionally the same or different and selected from the substituent group β. 1 to 2 groups]
A substituted 5- to 6-membered aromatic heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom [the substituent is substituted as an essential one; A 4- to 8-membered heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom (the substituents are the same or different and are selected from the substituent group β) And optionally represents the same or different and 1 to 2 groups selected from the substituent group β], or
An optionally substituted 8- to 10-membered aromatic heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom (the substituents may be the same or different, 1 to 3 groups selected from group β)
The sulfonamide compound or a pharmacologically acceptable salt thereof according to claim 2, wherein R ^1a is a group having the formula -NHCO-.
A ^1a may be a phenyl group which may be substituted (the substituents are the same or different and represent 1 to 3 groups selected from the substituent group α);
A substituted phenyl group [the substituent is, as essential, a 4- to 8-membered group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom, which may be substituted] A heterocyclyl group (the substituents are the same or different and represent 1 to 3 groups selected from the substituent group α), and are optionally the same or different and selected from the substituent group α; To 2 groups]
Optionally substituted 5- to 6-membered aromatic heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom (the substituents may be the same or different, 1 to 3 groups selected from group α), or
A substituted 5- to 6-membered aromatic heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom [the substituent is substituted as an essential one; A 4- to 8-membered heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom (the substituents may be the same or different and selected from the substituent group α) 1 to 3 groups, and optionally, the same or different and 1 to 2 groups selected from the substituent group α are represented]
A ^2a is a phenyl group which may be substituted (the substituents are the same or different and each represent 1 to 3 groups selected from substituent group β);
An optionally substituted naphthyl group (the substituents are the same or different and represent 1 to 3 groups selected from substituent group β),
Optionally substituted 5- to 6-membered aromatic heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom (the substituents may be the same or different, 1 to 3 groups selected from group β), or
An optionally substituted 8- to 10-membered aromatic heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom (the substituents may be the same or different, 1 to 3 groups selected from group β)
A ^3a is a naphthyl group which may be substituted (the substituents are the same or different and each represent 1 to 3 groups selected from substituent group β), or a nitrogen atom which may be substituted, An 8- to 10-membered aromatic heterocyclyl group containing 1 to 4 atoms selected from the group consisting of an oxygen atom and a sulfur atom (the substituents are the same or different and are selected from 1 to 3 selected from the substituent group β) Number of groups)
The sulfonamide compound or a pharmacologically acceptable salt thereof according to claim 2, wherein R ^1a is a group having the formula -NHCO-.
A ^1a may be substituted, phenyl, thiazolyl, isothiazolyl, or pyridyl group (the substituents are the same or different and represent 1 to 2 groups selected from substituent group α1), or A substituted phenyl, thiazolyl, isothiazolyl or pyridyl group [the substituent is, as an essential one, one to four selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom; A 5- to 7-membered heterocyclyl group containing the following atoms (the substituents are the same or different and represent 1 to 2 groups selected from the substituent group α1), and the optional substituent group α1 Represents one group selected from]
A ^2a is a phenyl group which may be substituted (the substituents are the same or different and each represents 1 to 2 groups selected from the substituent group β1), or
A 5- to 6-membered aromatic heterocyclyl group containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom which may be substituted (the heterocyclyl group is one or more nitrogen atoms) And may contain an oxygen atom and a sulfur atom, and the substituents are the same or different and represent 1 to 2 groups selected from the substituent group β1),
A ^3a is an optionally substituted naphthyl group (the substituents are the same or different and represent 1 to 2 groups selected from the substituent group β1), or a nitrogen atom, which may be substituted, 9 to 10-membered aromatic heterocyclyl group containing 1 to 4 atoms selected from the group consisting of oxygen atom and sulfur atom (the heterocyclyl group contains one or more nitrogen atoms, oxygen atom and sulfur atom And the substituents are the same or different and represent 1 to 2 groups selected from the substituent group β1),
The sulfonamide compound or a pharmacologically acceptable salt thereof according to claim 2, wherein R ^1a is a group having the formula -NHCO-.
A ^1a is a substituted phenyl group [the substituent is, as an essential component, optionally containing 1 to 4 atoms selected from the group consisting of a nitrogen atom, an oxygen atom, and a sulfur atom. A 5- to 6-membered aromatic heterocyclyl group (the substituents are the same or different and represent 1 to 2 groups selected from the substituent group α2), and are optionally selected from the substituent group α2 Shows one group]
A ^2a is an optionally substituted phenyl or pyridyl group (the substituents are the same or different and represent 1 to 2 groups selected from the substituent group β2);
A ^3a is an optionally substituted naphthyl, quinolyl, isoquinolyl, quinazolinyl, or quinoxalinyl group (the substituents are the same or different and each represent one or two groups selected from substituent group β4) Yes,
The sulfonamide compound or a pharmacologically acceptable salt thereof according to claim 2, wherein R ^1a is a group having the formula -NHCO-.
A ^1a is a substituted phenyl group [this substituent is optionally substituted, pyrrolyl, pyrazolyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, triazolyl, or tetrazolyl group (The substituents are the same or different and represent one or two groups selected from the substituent group α3), and optionally, one group selected from the substituent group α3] And
A ^2a is a phenyl group which may be substituted (the substituents are the same or different and represent 1 to 2 groups selected from the substituent group β3);
A ^3a is an optionally substituted naphthyl or quinolyl group (the substituents are the same or different and each represent one or two groups selected from substituent group β5);
The sulfonamide compound or a pharmacologically acceptable salt thereof according to claim 2, wherein R ^1a is a group having the formula -NHCO-.