WO2014123203A1

WO2014123203A1 - Therapeutic agent for diabetes

Info

Publication number: WO2014123203A1
Application number: PCT/JP2014/052803
Authority: WO
Inventors: 俊吉田中; 正樹福井; 一弥小竹; 正恭笠井; 弘明白波瀬
Original assignee: 京都薬品工業株式会社
Priority date: 2013-02-06
Filing date: 2014-02-06
Publication date: 2014-08-14
Also published as: JPWO2014123203A1

Abstract

Provided is a compound having PTP-1B inhibitory activity that is excellent as a drug, or a pharmaceutically acceptable salt thereof. A compound represented by general formula (I) (in the formula, each symbol means the same as in the specification), or a pharmaceutically acceptable salt thereof.

Description

Diabetes medicine

The present invention relates to a compound having a protein tyrosine phosphatase-1B (PTP-1B; Protein Tyrosine Phosphatase-1B) inhibitory activity, a blood glucose lowering action, a blood lipid lowering action and / or an insulin resistance improving action, or a pharmaceutical thereof Relates to acceptable salts. The present invention also relates to a pharmaceutical composition comprising the above compound or a pharmaceutically acceptable salt thereof. Furthermore, the present invention provides a therapeutic agent for diabetes, an insulin resistance improving agent, a glucose intolerance improving agent, a therapeutic agent for diabetic complications, an antiobesity agent, an antihyperglycemia comprising the above compound or a pharmaceutically acceptable salt thereof. The present invention relates to a prophylactic agent, a therapeutic agent for fatty liver, an antihyperlipidemic agent, an anti-arteriosclerosis agent, an anti-inflammatory agent, an anticancer agent, a prophylactic / therapeutic agent for diseases mediated by PTP-1B, and a prophylactic / therapeutic agent for metabolic syndrome.

Diabetes is a disease that causes various metabolic abnormalities, mainly chronic hyperglycemia, and causes various complications such as retinopathy, nephropathy, peripheral neuropathy, myocardial infarction based on arteriosclerosis, and cerebral infarction. cause. Metabolic syndrome is a state in which visceral fat obesity is combined with two or more of hyperglycemia, hypertension, and hyperlipidemia, and mortality due to coronary artery disease is high.

Diabetes is type I diabetes (insulin-dependent diabetes mellitus; IDDM) characterized by impaired insulin secretion mainly caused by islet cell destruction caused by autoantibody production against the islets, reduced insulin secretion from the pancreas, or skeletal muscle, Type II diabetes caused by insulin resistance in the liver, adipocytes, etc. (non-insulin dependent diabetes mellitus; NIDDM) is roughly classified. Currently, type II diabetic patients are rapidly increasing, accounting for over 90% of diabetic patients in Japan.
Representative therapeutic agents for type II diabetes include insulin secretagogues (sulfonylurea compounds, sulfonamide compounds, phenylalanine derivatives, GLP-1 analogs, DPP-4 inhibitors, etc.), biguanide compounds, α-glucosidase inhibition Agents, Peroxisome Proliferator-activated Receptor γ (PPARγ) activators (thiazolidinedione derivatives, etc.). Among these, biguanide compounds and PPARγ activators increase the sensitivity of insulin and lower blood sugar independently of insulin secretion. However, biguanide compounds cause lactic acidosis, diarrhea, and vomiting, and PPARγ activators can cause side effects such as liver damage, weight gain, fluid retention, hemodilution, edema, cardiac hypertrophy, and increased risk of fracture. The development of a therapeutic agent for insulin-sensitized diabetes that has been reported and is more effective and safe is desired.

Insulin is a hormone related to blood glucose regulation made by pancreatic β cells. When secreted insulin binds to insulin receptors on the surface of membranes such as skeletal muscle cells, hepatocytes, and adipocytes, tyrosine kinases phosphorylate tyrosine residues in the intracellular domain of insulin receptors . Subsequently, tyrosine residues such as IRS (insulin receptor substrate) and APS (adapter protein containing PH and SH2 domain), which are insulin receptor substrates, are phosphorylated, and the PI3 kinase-Akt pathway is activated. Is transferred onto the cell membrane, glucose uptake occurs, and the sugar concentration in the blood decreases. On the other hand, there is also a tyrosine phosphatase that negatively regulates intracellular signal transduction by insulin by dephosphorylating phosphorylated tyrosine, suppressing the action of insulin. That is, tyrosine phosphorylation in insulin signaling is regulated by the balance between tyrosine kinase and tyrosine phosphatase. Thus, insulin action is enhanced by inhibiting tyrosine phosphatase. In addition, when this balance is broken due to an abnormal increase in tyrosine phosphatase, tyrosine dephosphorylation is increased, leading to a decrease in insulin action, that is, insulin resistance. Therefore, also in this case, insulin resistance can be improved by inhibiting tyrosine phosphatase.

Tyrosine phosphatase is also involved in signal transduction of leptin, a peptide hormone secreted from adipocytes. Leptin is a hormone involved in the suppression of obesity, which has a strong inhibitory effect on food intake and energy consumption. The leptin signal, like the insulin signal, is regulated by tyrosine kinases and tyrosine phosphatases to phosphorylate tyrosine residues in the intracellular domain of the leptin receptor. Therefore, when tyrosine phosphatase activity is enhanced, dephosphorylation of phosphorylated tyrosine is enhanced, leading to leptin resistance (Non-patent Document 1).

Currently, various tyrosine phosphatases are known. Among them, PTP-1B is considered to be a major phosphatase involved in insulin and leptin signaling. In particular, PTP-1B gene expression is increased in high glucose culture, and its intracellular localization is changed to reduce insulin receptor and IRS-1 tyrosine phosphorylation, thereby inducing insulin resistance (non-patented). References 2, 3), introduction of wild-type PTP-1B impairs translocation of the sugar transporter GLUT4, and further enhances insulin sensitivity in PTP-1B knockout mice, and also against high-fat diet It becomes obesity resistant (Non-Patent Document 4), and PTP-1B knockout mice exhibit increased insulin sensitivity, increased energy metabolism, and decreased white adipose fine tissue weight (Non-Patent Document 5). It has been reported. Therefore, a drug that suppresses and / or inhibits the activation of PTP-1B inhibits dephosphorylation by PTP-1B and enhances insulin and leptin signaling, thereby causing diabetes due to insulin resistance and leptin resistance. It is thought to improve obesity and the like. Since this PTP-1B inhibitor has a novel action of normalizing and enhancing intracellular signal transduction, it can be a new type of diabetes therapeutic agent that avoids the problems of existing diabetes therapeutic agents.

Recently, various reports have been made on compounds aimed at treating diseases such as diabetes by inhibiting protein tyrosine phosphatase (Non-patent Documents 6 to 9 and Patent Documents 1 to 12). However, these publications do not disclose a compound having a structure such as the compound of the present invention, nor a statement to suggest it.

International Publication No. 99/46244 International Publication No. 99/58520 International Publication No. 03/048140 Japanese Patent Laid-Open No. 2005-112802 International Publication No. 2007/009911 International Publication No. 2007/032028 International Publication No. 2007/088857 International Publication No. 2008/070552 International Publication No. 2009/109998 JP 2010-43130 A Special table 2010-520240 gazette JP 2011-256174 A

It is an object of the present invention to have an excellent PTP-1B inhibitory activity and good oral absorbability, and further exhibits a blood glucose lowering action, a blood lipid lowering action and / or an insulin resistance improving action, and is safe with few side effects It is to provide a therapeutic agent for diabetes with a high level of diabetes.

As a result of intensive studies to solve the above problems, the present inventors have found that a compound represented by the following general formula (I) having a novel structure or a pharmaceutically acceptable salt thereof is PTP-1B. Since it has an inhibitory action and exhibits such actions as a blood glucose lowering action, a blood lipid lowering action, an insulin resistance improving action, etc., it has been found to be an extremely excellent compound as a pharmaceutical, and the present invention has been completed. It was.

That is, the present invention
[1] General formula (I):

{Where,
A represents an optionally substituted carbocyclic group, an optionally substituted biaryl, or an optionally substituted heterocyclic group;
B represents an optionally substituted divalent carbocyclic group, an optionally substituted biarylene, or an optionally substituted divalent heterocyclic group;
C is an optionally substituted carbocyclic group, an optionally substituted biaryl, an optionally substituted arylalkyl, an optionally substituted arylalkenyl, an optionally substituted alkyl, a substituted An optionally substituted alkenyl, an optionally substituted cycloalkyl, an optionally substituted cycloalkylalkyl, an optionally substituted heterocyclic group, or an optionally substituted heterocyclic alkenyl;
X is an optionally substituted alkylene, an optionally substituted alkenylene, an optionally substituted alkynylene, an optionally substituted * — (CH ₂ ) _m —O— (CH ₂ ) _n — * *, Optionally substituted * — (CH ₂ ) _m —S (O) _p — (CH ₂ ) _n — **, optionally substituted * — (CH ₂ ) _m —N (R ¹ ) — (CH ₂ ) _n — **, optionally substituted * — (CH ₂ ) _m —CO— (CH ₂ ) _n — **, optionally substituted * — (CH ₂ ) _q —CO —N (R ¹ ) — (CH ₂ ) _r — **, optionally substituted * — (CH ₂ ) _q —N (R ¹ ) —CO— (CH ₂ ) _r — **, substituted and may be _{_{_{^{* - (CH 2) q -SO}}}} 2 -N (R 1) - (CH 2) r - **, substituted _{_{^{_{* - (CH 2) q -N}}}} (R 1) -SO 2 - (CH 2) r - **, * - C (R 1) = N-O - **, or * -O-N = C ( R ¹ )-** (wherein m, n, q and r each independently represents 0 or an integer of 1 to 4, p represents 0, 1 or 2; R ¹ represents hydrogen; Represents an atom or lower alkyl, * represents a bonding position to A, ** represents a bonding position to B, and Z represents * -CONHSO ₂ -**, * -SO ₂ NHCO-**, * -N (R ² ) CONHSO ₂ -**, * -SO ₂ NHCON (R ² )-**, * -CONHSO ₂ N (R ² )-**, * -N (R ² ) SO ₂ NHCO-**, * -COCONHSO ₂ -**, * -SO ₂ NHCOCO-**, * -N (R ² ) COCONHSO _2- **, or * -SO ₂ NHCOCON (R ² )-** (wherein R ² represents a hydrogen atom or lower alkyl, * represents a bonding position with B, ** represents a bond with C Indicates the binding position). }
Or a pharmaceutically acceptable salt thereof (hereinafter also referred to as compound (I));
[1 ′] General formula (I ′):

(In the formula, A, C, X and Z are the same as the above [1].)
Or a pharmaceutically acceptable salt thereof;
[2] X is optionally substituted * — (CH ₂ ) ₃ — **, optionally substituted * — (CH ₂ ) _m —O— (CH ₂ ) _n — **, substituted * — (CH ₂ ) _m —S (O) _p — (CH ₂ ) _n — **, optionally substituted * — (CH ₂ ) _m —N (R ¹ ) — (CH ₂ ) _N -**, optionally substituted *-(CH ₂ ) _m -CO- (CH ₂ ) _n -**, optionally substituted *-(CH ₂ ) _q -CO-N (R ¹ ) — (CH ₂ ) _r — **, optionally substituted * — (CH ₂ ) _q —N (R ¹ ) —CO— (CH ₂ ) _r — **, optionally substituted * _{_{_{^{- (CH 2) q -SO 2}}}} -N (R 1) - (CH 2) r - **, optionally substituted _{_{^{* - (CH 2) q -N}}} (R 1) -SO 2 - ( H ₂₎ _r - **, or ^{* -C (R 1) = N} -O - ** ( wherein, m, n, q and r are each independently an integer of 0 or 1 to 4 , P is 0, 1 or 2, R ¹ is a hydrogen atom or lower alkyl, * represents the bonding position with A, and ** represents the bonding position with B, provided that m + n Is an integer of 2 or more, and q + r is an integer of 1 or more)) or a pharmaceutically acceptable salt thereof;
[3] X is —O—, —S (O) _p —, —N (R ¹ ) —, —CH (R ¹ ) —, —CO—, — (CH ₂ ) ₂ —, —CH═CH —, —CO—N (R ¹ ) —, —N (R ¹ ) —CO—, —SO ₂ —N (R ¹ ) —, or —N (R ¹ ) —SO ₂ — (where R ¹ Is a hydrogen atom or lower alkyl, and p is 0, 1 or 2.) The compound of the above-mentioned [1] or a pharmaceutically acceptable salt thereof;
[4] X may be substituted * — (CH ₂ ) _m —O— (CH ₂ ) _n — **, optionally substituted * — (CH ₂ ) _m —S (O) _p — (CH ₂ ) _n — **, or * —C (R ¹ ) = N—O — **, wherein m and n are each independently 0 or an integer of 1 to 4; Is 0, 1 or 2, R ¹ is a hydrogen atom or lower alkyl, * represents the bonding position with A, and ** represents the bonding position with B, where m + n is Or an integer of 2 or more)), or a pharmaceutically acceptable salt thereof;
[5] B is an optionally substituted biarylene, or an optionally substituted divalent aromatic heterocyclic group,
X may be substituted * — (CH ₂ ) _m —O— (CH ₂ ) _n — **, or may be substituted * — (CH ₂ ) _m —S (O) _p — ( CH ₂ ) _n -** (wherein, m and n are each independently 0 or an integer of 1 to 4, p is 0, 1 or 2, and * is the position of bonding with A) ** indicates the position of binding to B.)
Or a pharmaceutically acceptable salt thereof according to the above [1];
[6] B is phenylene which may be substituted,
X is * — (CH ₂ ) _m —O— (CH ₂ ) _n — **, * — (CH ₂ ) _m —S— (CH ₂ ) _n — **, or * —CH═N—O—. ** (wherein, m and n are each independently an integer of 1 to 4, * represents a bonding position with A, and ** represents a bonding position with B).
Or a pharmaceutically acceptable salt thereof according to the above [1];
[7] Z is * -CONHSO ₂ -**, * -SO ₂ NHCO-**, * -NHCONHSO ₂ -**, * -CONHSO ₂ NH-**, * -CONCONHSO ₂ -**, or * Any one of [1] to [6] above, which is —NHCOCONHSO ₂ — ** (wherein * represents a bonding position with B and ** represents a bonding position with C). Or a pharmaceutically acceptable salt thereof;
[8] The compound according to any one of [1] and [5] to [7] above, wherein X is —CH ₂ —O—CH ₂ — or —CH ₂ —S—CH ₂ — or a pharmaceutical thereof Top acceptable salts;
[9] The compound or a pharmaceutically acceptable salt thereof according to any one of the above [1] to [8], wherein C is aryl which may be substituted;
[10] The compound or a pharmaceutically acceptable salt thereof according to any one of the above [1] to [8], wherein C is alkyl which may be substituted or cycloalkylalkyl which may be substituted. ;
[11] The compound represented by the general formula (I) is:
(1) N- [4- (biphenyl-4-ylmethylsulfanylmethyl) benzoyl] octane-1-sulfonamide,
(2) N- [4- (biphenyl-4-ylmethoxymethyl) benzoyl] -2,4-dichlorobenzenesulfonamide,
(3) N- [4- (biphenyl-4-ylmethoxymethyl) benzoyl] octane-1-sulfonamide,
(4) N- [4- (biphenyl-4-ylmethylsulfanylmethyl) benzoyl] hexane-1-sulfonamide,
(5) N- [4- (biphenyl-4-ylmethylsulfanylmethyl) benzoyl] -4-cyclopropylbutane-1-sulfonamide,
(6) N- [4- (biphenyl-4-ylmethoxymethyl) benzoyl] heptane-1-sulfonamide, or (7) N- [4- (biphenyl-4-ylmethoxymethyl) benzoyl] -5-cyclo The compound of the above-mentioned [1], which is propylpentane-1-sulfonamide, or a pharmaceutically acceptable salt thereof;
[12] The compound represented by the general formula (I) is:
(1) 4- (4-Isopropylbenzyloxymethyl) -N- (heptylaminosulfonyl) benzamide,
(2) N- {2- [4- (4-isopropylbenzyloxymethyl) phenyl] -2-oxoacetyl} octane-1-sulfonamide,
(3) N- [4- (4-isopropylbenzyloxymethyl) phenyl] -2- (octane-1-sulfamoylamino) -2-oxoacetamide,
(4) N- [4- (biphenyl-4-ylmethylsulfanylmethyl) phenyl] -2- (hexane-1-sulfonylamino) -2-oxoacetamide, or (5) N- {2- [4- (biphenyl) -4-ylmethylsulfanylmethyl) phenyl] -2-oxoacetyl} hexane-1-sulfonamide, the compound according to the above [1] or a pharmaceutically acceptable salt thereof;
[13] The compound represented by the general formula (I) is:
(1) N- [4- (3′-methoxybiphenyl-4-ylmethylsulfanylmethyl) benzoyl] hexane-1-sulfonamide,
(2) N- {4- [3 ′-(trifluoromethyl) biphenyl-4-ylmethylsulfanylmethyl] benzoyl} hexane-1-sulfonamide,
(3) N- {4- [4- (1,4-benzodioxan-6-yl) benzylsulfanylmethyl] benzoyl} hexane-1-sulfonamide,
(4) N- {4- [3 ′-(trifluoromethyl) biphenyl-4-ylmethoxymethyl] benzoyl} hexane-1-sulfonamide, or (5) N- [4- (3′-methoxybiphenyl- 3-ylmethylsulfanylmethyl) benzoyl] hexane-1-sulfonamide, the compound according to the above [1] or a pharmaceutically acceptable salt thereof;
[14] The compound represented by the general formula (I) is:
(1) (E) -N-({4- [3 ′-(trifluoromethyl) biphenyl-4-yl] methyleneaminooxy} benzoyl) hexane-1-sulfonamide,
(2) (E) -N-({4- [4- (1,4-benzodioxan-6-yl) phenyl] methyleneaminooxy} benzoyl) hexane-1-sulfonamide,
(3) (E) -N- [4- (3′-dimethylaminobiphenyl-4-ylmethyleneaminooxy) benzoyl] hexane-1-sulfonamide, or (4) (E) -N- [4- ( [3] -methoxybiphenyl-4-ylmethyleneaminooxy) benzoyl] hexane-1-sulfonamide or a pharmaceutically acceptable salt thereof;
[15] The compound represented by the general formula (I) is:
(1) N-{[4- (3′-methoxybiphenyl-4-ylmethylsulfanylmethyl) phenyl] -2-oxoacetyl} hexane-1-sulfonamide, or (2) N-({4- [4 -(1,4-benzodioxan-6-yl) benzylsulfanylmethyl] phenyl} -2-oxoacetyl) hexane-1-sulfonamide, the compound according to the above [1] or a pharmaceutically acceptable salt thereof;
[16] A pharmaceutical composition comprising the compound according to any one of [1] to [15] above or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier;
[17] A PTP-1B inhibitor comprising as an active ingredient the compound according to any one of [1] to [15] above or a pharmaceutically acceptable salt thereof;
[18] A medicament containing the PTP-1B inhibitor according to [17] as an active ingredient;
[19] The pharmaceutical composition according to the above [16], for preventing or treating a disease involving PTP-1B;
[20] The pharmaceutical composition according to [16] above, for the prevention or treatment of a disease selected from the group consisting of diabetes, hyperglycemia, diseases caused by insulin resistance, diabetic complications, and impaired glucose tolerance;
[21] The pharmaceutical composition according to [16] above for preventing or treating a disease selected from the group consisting of arteriosclerosis, hyperlipidemia, obesity, cancer, inflammatory disease and metabolic syndrome;
And so on.

Since the compound represented by the above general formula (I) of the present invention or a pharmaceutically acceptable salt thereof has a PTP-1B inhibitory action, it has a blood glucose lowering action, a blood lipid lowering action and / or an insulin resistance improvement. Antihyperglycemic agent, antihyperlipidemic agent, insulin resistance improving agent, diabetes treatment agent, diabetic complication treatment agent, glucose intolerance improving agent, anti-arteriosclerosis agent, anti-obesity agent, anti-hyperglycemic agent It is useful as an inflammatory agent, a prophylactic / therapeutic agent for diseases mediated by PTP-1B, and a prophylactic / therapeutic agent for metabolic syndrome. Moreover, since the pharmaceutical which contains this invention compound as an active ingredient has few side effects, it can become a highly safe therapeutic agent for diabetes.

The present invention will be described in detail below.

Definitions of terms and symbols used in this specification will be described below.
In the present specification, the “halogen atom” refers to a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

In this specification, the term “lower” for an organic group such as an alkyl group means that the number of carbon atoms is 1 to 6.

In the present specification, “alkyl” refers to a linear or branched monovalent saturated hydrocarbon group having 1 to 12 carbon atoms (hereinafter sometimes referred to as C _1-12 alkyl. The same applies to others. .) Examples of the “alkyl” include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, neopentyl, 4-methylpentyl, hexyl, heptyl, octyl, nonyl, decyl. , Undecyl, dodecyl and the like.

In the present specification, “cycloalkyl” means a monovalent group derived from a saturated hydrocarbon ring having 3 to 10 carbon atoms. Further, “cycloalkyl” may be bridged. Examples of the “cycloalkyl” include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl and the like.

In the present specification, “alkenyl” means a linear or branched monovalent hydrocarbon group having one or more carbon-carbon double bonds and having 2 to 10 carbon atoms. Examples of the “alkenyl” include vinyl, 1-propenyl (allyl), 2-propenyl, isopropenyl, 2-methyl-1-propenyl, 1-butenyl, 2-butenyl, 3-butenyl and 2-butene-2. -Yl, 3-methyl-2-butenyl, 3-methyl-2-buten-2-yl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 5-pentenyl, 2-penten-2-yl 2-penten-3-yl, 4-methyl-1-pentenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 5-methyl-1-hexenyl, butadienyl (eg, buta-1,3-diene-1 -Yl), pentadienyl (eg, penta-1,3-dien-1-yl), heptatrienyl (eg, hepta-1,3,5-trien-1-yl), etc. .

In the present specification, “cycloalkenyl” means a monovalent group derived from a partially unsaturated hydrocarbon ring having 3 to 10 carbon atoms. Further, “cycloalkenyl” may be cross-linked. Examples of the “cycloalkenyl” include cyclopropenyl (eg, 2-cyclopropen-1-yl), cyclobutenyl (eg, 2-cyclobuten-1-yl), cyclopentenyl (eg, 1-cyclopenten-1-yl). 2-cyclopenten-1-yl, 3-cyclopenten-1-yl), cyclohexenyl (eg, 1-cyclohexen-1-yl, 2-cyclohexen-1-yl, 3-cyclohexen-1-yl) and the like It is done.

In the present specification, “alkynyl” means a linear or branched monovalent hydrocarbon group having one or more carbon-carbon triple bonds and having 2 to 10 carbon atoms. The “alkynyl” may have one or more carbon-carbon double bonds in addition to one or more carbon-carbon triple bonds. Examples of the “alkynyl” include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl and 1-hexynyl. 2-hexynyl, 3-hexynyl, 3,3-dimethyl-1-butynyl, propadiynyl (eg, propa-1,3-diin-1-yl), prop-1-en-3-in-1-yl, etc. ).

In the present specification, “cycloalkylalkyl” means a monovalent group in which the “cycloalkyl” group is bonded to the “alkyl” group. Examples of the “cycloalkylalkyl” include cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cycloheptylmethyl, cyclooctylmethyl, cyclopropylethyl, cyclobutylethyl, cyclopentylethyl, cyclohexylethyl, cycloheptylethyl. , Cyclooctylethyl, cyclopropylpropyl, cyclobutylpropyl, cyclopentylpropyl, cyclohexylpropyl, cycloheptylpropyl, cyclooctylpropyl, cyclopropylbutyl, cyclopropylpentyl and the like.

In the present specification, “alkylene” means a linear or branched divalent saturated hydrocarbon group having 1 to 10 carbon atoms. Examples include methylene, ethylene, propylene, butylene, pentylene, hexylene, heptylene, 2,2-dimethylethylene, 2,2-dimethylpropylene and the like.

In the present specification, “alkenylene” means a linear or branched divalent hydrocarbon group having one or more carbon-carbon double bonds and having 2 to 10 carbon atoms. Examples of the “alkenylene” include vinylene, propenylene, butenylene, pentenylene, hexenylene, heptenylene, octenylene and the like.

In the present specification, “alkynylene” means a linear or branched divalent hydrocarbon group having one or more carbon-carbon triple bonds and having 2 to 10 carbon atoms. Examples of the “alkynylene” include ethynylene, propynylene, butynylene, pentynylene, hexynylene, heptynylene, octynylene and the like.

In this specification, “carbocyclic group” means aryl and non-aromatic carbocyclic groups.

In the present specification, “aryl” means a monovalent aromatic hydrocarbon group having 6 to 14 carbon atoms. Examples of the “aryl” include phenyl, naphthyl (eg, 1-naphthyl, 2-naphthyl), acenaphthylenyl, azulenyl, anthryl, phenanthryl and the like.
In the present specification, the “aromatic hydrocarbon” includes a ring corresponding to the above “aryl”.

In the present specification, the “non-aromatic carbocyclic group” means a monovalent saturated or partially saturated cyclic hydrocarbon group having 3 to 14 carbon atoms. Examples of the “non-aromatic carbocyclic group” include cycloalkyl, cycloalkenyl, condensed non-aromatic carbocyclic group and the like.

In the present specification, the “fused non-aromatic carbocyclic group” means a carbocyclic group in which an cycloalkyl or cycloalkenyl and an aromatic hydrocarbon are condensed, for example, indanyl (eg, 2-indanyl, 5-indanyl). , Indenyl (eg, 2-indenyl, 5-indenyl), fluorenyl (eg, 2-fluorenyl, 9-fluorenyl) and the like.

In the present specification, “arylalkyl” means a monovalent group in which the “aryl” group is bonded to the “alkyl” group. Examples of the “arylalkyl” include benzyl, naphthylmethyl, phenylethyl, naphthylethyl, phenylpropyl, naphthylpropyl and the like.

In the present specification, “arylalkenyl” means a monovalent group in which the “aryl” group is bonded to the “alkenyl” group. Examples of the “arylalkenyl” include phenylvinyl, naphthylvinyl, phenylbutadienyl (eg, 4-phenylbuta-1,3-dien-1-yl) and the like.

In the present specification, “arylalkynyl” means a monovalent group in which the “aryl” group is bonded to the “alkynyl” group. Examples of the “arylalkynyl” include phenylethynyl, naphthylethynyl and the like.

In the present specification, “alkoxy” means a group in which the “alkyl” group is bonded to an oxygen atom, that is, a linear or branched alkoxy group having 1 to 10 carbon atoms. Examples of the “alkoxy” include methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, tert-butoxy, pentyloxy, isopentyloxy, neopentyloxy, hexyloxy and the like.

In the present specification, “cycloalkoxy” means a group in which the “cycloalkyl” group is bonded to an oxygen atom. Examples of the “cycloalkoxy” include cyclopropoxy, cyclobutoxy, cyclopentyloxy, cyclohexyloxy and the like.

In the present specification, “arylalkyloxy” means a monovalent group in which the “arylalkyl” group is bonded to an oxygen atom. The “arylalkyloxy” is a monovalent group in which the “arylalkyl” is bonded to an oxygen atom, and examples thereof include benzyloxy, naphthylmethoxy, phenylethoxy, naphthylethoxy, phenylpropoxy, naphthylpropoxy and the like. .

In the present specification, “mono or di-alkylamino” means a group in which one or two “alkyl” groups are bonded to an amino group, that is, mono or di (straight or branched having 1 to 10 carbon atoms). Means a chain alkyl) amino group. Examples of the “mono or di-alkylamino” include methylamino, ethylamino, dimethylamino, diethylamino and the like.

In the present specification, “alkylsulfanyl” means a group in which the “alkyl” group is bonded to a sulfur atom, that is, a linear or branched alkylsulfanyl group having 1 to 10 carbon atoms. Examples of the “alkylsulfanyl” include, for example, methylsulfanyl, ethylsulfanyl, propylsulfanyl, isopropylsulfanyl, butylsulfanyl, isobutylsulfanyl, sec-butylsulfanyl, tert-butylsulfanyl, pentylsulfanyl, isopentylsulfanyl, neopentylsulfanyl, Xylsulfanyl and the like.

In the present specification, “alkylcarbonyl” means a group in which the “alkyl” group is bonded to a carbonyl group, that is, a linear or branched alkylcarbonyl group having 1 to 10 carbon atoms. Examples of the “alkylcarbonyl” include acetyl, propionyl and the like.

In the present specification, the “heterocyclic group” is a 3 to 14 member (monocyclic, bicyclic or tricyclic system) containing at least one heteroatom selected from the group consisting of an oxygen atom, a nitrogen atom and a sulfur atom. A heterocyclic group means an aromatic heterocyclic group and a non-aromatic heterocyclic group.
In the present specification, the “aromatic heterocyclic group” is a monovalent 5- to 14-membered monocyclic aromatic group containing at least one heteroatom selected from the group consisting of an oxygen atom, a nitrogen atom and a sulfur atom. It means a heterocyclic group and a condensed aromatic heterocyclic group. The fused aromatic heterocyclic group in the present invention is a 2 or 3 ring system, and a plurality of rings may have heteroatoms. The monocyclic aromatic heterocyclic group includes a 5- or 6-membered ring group, and the condensed aromatic heterocyclic group includes a group in which each ring constituting the group is a 5- or 6-membered ring. Examples of the “aromatic heterocyclic group” include monocyclic aromatic heterocyclic rings such as furyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, triazolyl, tetrazolyl, thiadiazolyl, oxadiazolyl, pyridyl, pyridazinyl, pyrimidinyl and the like. Groups, indolyl, isoindolyl, indazolyl, benzofuryl, benzothiophenyl, benzoimidazolyl (eg, 5-benzoimidazolyl), benzoxazolyl, benzothiazolyl, quinolyl, isoquinolyl, benzoxazinyl, benzothiazinyl, furo [2,3-b] Pyridyl, thieno [2,3-b] pyridyl, naphthyridinyl, imidazopyridyl, oxazolopyridyl, thiazolopyridyl, quinolyl, carbazolyl, dibenzothiophenyl, etc. It includes ring aromatic heterocyclic group.

In the present specification, the “non-aromatic heterocyclic group” means a monovalent 3- to 14-membered monocyclic non-cyclic group containing at least one heteroatom selected from the group consisting of an oxygen atom, a nitrogen atom and a sulfur atom. An aromatic heterocyclic group and a fused non-aromatic heterocyclic group are meant. The fused non-aromatic heterocyclic group in the present invention is a 2 or 3 ring system and may have a hetero atom in both rings. The monocyclic non-aromatic heterocyclic group includes a 5- to 9-membered ring group, and the condensed aromatic heterocyclic group includes a group in which each ring constituting the group is a 5- or 6-membered ring. . Examples of the “non-aromatic heterocyclic group” include tetrahydrofuryl, oxazolidinyl, imidazolinyl (eg, 1-imidazolinyl, 2-imidazolinyl, 4-imidazolinyl), aziridinyl (eg, 1-aziridinyl, 2-aziridinyl), azetidinyl (Eg, 1-azetidinyl, 2-azetidinyl), pyrrolidinyl (eg, 1-pyrrolidinyl, 2-pyrrolidinyl, 3-pyrrolidinyl), piperidyl (eg, 1-piperidyl, 2-piperidyl, 3-piperidyl), azepanyl (eg, 1-azepanyl, 2-azepanyl, 3-azepanyl, 4-azepanyl), azocanyl (eg, 1-azocanyl, 2-azocanyl, 3-azocanyl, 4-azocanyl), azonanyl (eg, 1-azonanyl, 2-azonanyl, 3-azonanyl, 4-azonanyl, 5-azona ), Piperazinyl (eg, 1,4-piperazin-1-yl, 1,4-piperazin-2-yl), diazepinyl (eg, 1,4-diazepin-1-yl, 1,4-diazepine-2- Yl, 1,4-diazepin-5-yl, 1,4-diazepin-6-yl), diazocanyl (eg, 1,4-diazocan-1-yl, 1,4-diazocan-2-yl, 1,4 -Diazocan-5-yl, 1,4-diazocan-6-yl, 1,5-diazocan-1-yl, 1,5-diazocan-2-yl, 1,5-diazocan-3-yl), tetrahydropyrani Monocyclic (eg, tetrahydropyran-4-yl), morpholinyl (eg, 4-morpholinyl), thiomorpholinyl (eg, 4-thiomorpholinyl), 2-oxazolidinyl, dihydrofuryl, dihydropyranyl, etc. Aromatic heterocyclic groups, dihydrobenzofuryl, dihydroquinolyl, dihydroisoquinolyl (eg, 3,4-dihydroisoquinolin-2-yl), dihydroindolyl (eg, 2,3-dihydroindol-5-yl, 2,3-dihydroindol-1-yl), dihydroisoindolyl (eg, 2,3-dihydroisoindol-2-yl), benzodioxanyl (eg, 1,4-benzodioxan-6-yl) And condensed non-aromatic heterocyclic groups such as benzodioxolyl (eg, 1,3-benzodioxol-5-yl).

In this specification, “biaryl” is a monovalent group in which the “aryl” groups are directly bonded, a monovalent group in which the “aromatic heterocyclic” groups are directly bonded, or the “aryl” group. It means a monovalent group to which the “aromatic heterocycle” group is directly bonded. Examples of the “biaryl” include biphenylyl (eg, 4-biphenylyl, 3-biphenylyl), bipyridyl, pyridylphenyl, phenylpyridyl and the like.

In the present specification, the “aromatic heterocyclic alkyl” means a monovalent group in which the “aromatic heterocyclic group” is bonded to the “alkyl” group. Examples of the “aromatic heterocyclic alkyl” include pyridylmethyl and the like.
In the present specification, the “aromatic heterocyclic alkenyl” means a monovalent group in which the “aromatic heterocyclic group” is bonded to the “alkenyl” group. Examples of the “aromatic heterocyclic alkenyl” include furylbutadienyl (eg, 4- (2-furyl) buta-1,3-dien-1-yl) and the like.

In the present specification, “aromatic heterocyclic alkynyl” means a monovalent group in which the “aromatic heterocyclic group” is bonded to the “alkynyl” group. Examples of the “aromatic heterocyclic alkynyl” include thiazolylethynyl (eg, thiazol-2-ylethynyl) and the like.

In the present specification, the “divalent carbocyclic group” means arylene and a divalent non-aromatic carbocyclic group.

In the present specification, “arylene” means a divalent aromatic hydrocarbon group derived from the “aryl” group. Examples of the “arylene” include benzene-1,4-diyl (hereinafter also referred to as 1,4-phenylene), benzene-1,3-diyl, benzene-1,2-diyl (hereinafter, 1,2-phenylene). Phenylene), naphthalene-1,8-diyl (hereinafter also referred to as 1,8-naphthylene), naphthalene-1,5-diyl (hereinafter also referred to as 1,5-naphthylene), anthracene-1,4-diyl Etc.

In the present specification, the “divalent non-aromatic carbocyclic group” means a cycloalkylene, cycloalkenylene, divalent fused non-aromatic carbocyclic group.
In the present specification, “cycloalkylene” means a divalent saturated carbocyclic group derived from the “cycloalkyl” group. Examples of the “cycloalkylene” include cyclopropylene, cyclobutane-diyl, cyclopentane-diyl, cyclohexane-diyl and the like.

In the present specification, “cycloalkenylene” means a divalent partially saturated carbocyclic group derived from the “cycloalkenyl” group. Examples of the “cycloalkenylene” include cyclopropene-diyl, cyclobutene-diyl, cyclopentene-diyl, cyclohexene-diyl and the like.

In the present specification, the “divalent fused non-aromatic carbocyclic group” means a divalent carbocyclic group derived from the “fused non-aromatic carbocyclic group”. Examples of the “divalent fused non-aromatic carbocyclic group” include indan-diyl and the like.

In the present specification, the “divalent heterocyclic group” is a 3- to 14-membered (monocyclic, bicyclic or tricyclic) containing at least one heteroatom selected from the group consisting of an oxygen atom, a nitrogen atom and a sulfur atom. Ring system) means a divalent group derived from a heterocyclic ring, and includes a divalent aromatic heterocyclic group and a divalent non-aromatic heterocyclic group.

In the present specification, the “divalent aromatic heterocyclic group” means a monocyclic aromatic heterocyclic ring or condensed aromatic group containing at least one heteroatom selected from the group consisting of an oxygen atom, a nitrogen atom and a sulfur atom. Means a divalent group derived from a heterocyclic group. Examples of the “divalent aromatic heterocyclic group” include furan-2,5-diyl (hereinafter also referred to as 2,5-furylene), thiophene-2,4-diyl, thiophene-2,5-diyl. (Hereinafter also referred to as 2,5-thienylene), 1,3,4-oxadiazole-2,5-diyl, 1,3,4-thiadiazole-2,5-diyl, 1,3-thiazole-2, 4-diyl, 1,3-thiazole-2,5-diyl, pyridine-2,4-diyl, pyridine-2,3-diyl, pyridine-2,5-diyl, pyridine-2,6-diyl, pyridazine- 3,6-diyl, quinoline-2,3-diyl, quinoline-3,7-diyl, quinoline-5,8-diyl, indole-2,6-diyl, benzofuran-2,5-diyl, benzofuran-2, 6-Diyl, benzimida Lumpur-2,5-diyl, benzoxazole-2,6-diyl, carbazole-3,9-diyl.

In the present specification, the “divalent non-aromatic heterocyclic group” means a monocyclic non-aromatic heterocyclic ring containing at least one heteroatom selected from the group consisting of an oxygen atom, a nitrogen atom and a sulfur atom, or It means a divalent group derived from a fused non-aromatic heterocyclic ring. Examples of the “divalent non-aromatic heterocyclic group” include piperidine-diyl, dihydroindole-diyl and the like.

In the present specification, “biarylene” means a divalent group derived from the “biaryl”. Examples of the “biarylene” include biphenylene (eg, 4,4′-biphenylene, 2,4′-biphenylene), phenylpyridine-diyl, phenylpyrazole-diyl, phenylpyridazine-diyl, phenylpyrazine-diyl, pyrazolylpyridazine -Diyl, pyrazolylpyrazine-diyl and the like.

(Preferred Compound Embodiment of the Present Invention)
The symbols in formula (I) will be described below.

A represents an optionally substituted carbocyclic group, an optionally substituted biaryl, or an optionally substituted heterocyclic group.

The “carbocyclic group” of the “optionally substituted carbocyclic group” represented by A is preferably a C _6-14 aryl or condensed non-aromatic carbocyclic group, more preferably phenyl, naphthyl ( Examples, 1-naphthyl), indanyl (eg, 2-indanyl, 5-indanyl), fluorenyl (eg, 2-fluorenyl) and the like.
The “carbocyclic group” may have one or more (preferably 1 to 3, more preferably 1 or 2) substituents at any substitutable position. Examples of such a substituent include the following substituent group A. When the number of the substituents is 2 or more, these substituents may be the same or different.

[Substituent group A]
(1) a halogen atom,
(2) hydroxy,
(3) Carboxy,
(4) Cyano,
(5) Nitro,
(6) (i) a halogen atom, and (ii) an alkyl optionally substituted with 1 to 5 substituents selected from arylalkoxy optionally substituted with alkyl,
(7) arylalkyl,
(8) aromatic heterocyclic alkyl,
(9) Alkenyl,
(10) arylalkenyl,
(11) aromatic heterocyclic alkenyl,
(12) alkynyl,
(13) arylalkynyl,
(14) aromatic heterocyclic alkynyl,
(15) alkoxy,
(16) aryloxy,
(17) aromatic heterocyclic oxy,
(18) amino,
(19) mono- or di-alkylamino,
(20) cycloalkyl,
(21) cycloalkoxy,
(22) (i) a halogen atom, and (ii) aryl optionally substituted with 1 to 3 substituents selected from alkyl optionally substituted with 1 to 7 halogen atoms,
(23) a non-aromatic heterocyclic group, and
(24) An aromatic heterocyclic group optionally substituted with 1 to 3 alkyls.

The “optionally substituted carbocyclic group” is preferably
(1) (a) a halogen atom (eg, chlorine atom),
(b) Nitro,
(c) alkyl (eg, methyl, isopropyl, tert-butyl, hexyl) optionally substituted with 1 to 5 halogen atoms (eg, fluorine atom),
(d) alkenyl (eg, 2-methyl-1-propenyl, 4-methyl-1-pentenyl, 5-methyl-1-hexenyl),
(e) arylalkenyl [eg, phenyl vinyl (eg, 2-phenyl vinyl)],
(f) alkynyl (eg, ethynyl),
(g) arylalkynyl (eg, phenylethynyl),
(h) heterocyclic alkynyl [eg, thiazolylethynyl (eg, thiazol-5-ylethynyl)],
(i) alkoxy (eg, isopropoxy),
(j) mono- or di-alkylamino (eg ethylamino, dimethylamino, diethylamino),
(k) cycloalkyl (eg, cyclobutyl),
(l) (i) a halogen atom (eg, fluorine atom, chlorine atom), and (ii) an alkyl optionally substituted with 1 to 7 halogen atoms (eg, fluorine atom) (eg, methyl, isopropyl)
Aryl (eg, phenyl) optionally substituted with 1 to 3 (preferably 1 or 2) substituents selected from
(m) non-aromatic heterocyclic group [eg, pyrrolidinyl (eg, 1-pyrrolidinyl)], and (n) aromatic heterocyclic group [eg, furyl (eg, 2-furyl), thienyl (eg, 2-thienyl) ), Pyrrolyl (eg, 1-pyrrolyl), thiadiazolyl (eg, 1,3,4-thiadiazol-2-yl)]
6- to 14-membered carbocyclic group optionally substituted by 1 to 3 (preferably 1 or 2) substituents selected from [eg, phenyl, indanyl (eg, 2-indanyl, 5- Indanyl), naphthyl (eg, 1-naphthyl), fluorenyl (eg, 2-fluorenyl)] and the like.

In another embodiment, the “optionally substituted carbocyclic group” is preferably
(1) (a) a halogen atom (eg, chlorine atom),
(b) Nitro,
(c) alkyl (eg, methyl, isopropyl, tert-butyl, hexyl) optionally substituted with 1 to 5 halogen atoms (eg, fluorine atom),
(d) alkenyl (eg, 2-methyl-1-propenyl, 4-methyl-1-pentenyl, 5-methyl-1-hexenyl),
(e) arylalkenyl [eg, phenyl vinyl (eg, 2-phenyl vinyl)],
(f) alkynyl (eg, ethynyl),
(g) arylalkynyl (eg, phenylethynyl),
(h) heterocyclic alkynyl [eg, thiazolylethynyl (eg, thiazol-5-ylethynyl)],
(i) alkoxy (eg, methoxy, isopropoxy),
(j) mono- or di-alkylamino (eg ethylamino, dimethylamino, diethylamino),
(k) cycloalkyl (eg, cyclobutyl),
(l) (i) a halogen atom (eg, fluorine atom, chlorine atom),
(ii) alkyl (eg, methyl, isopropyl) optionally substituted with 1 to 7 halogen atoms (eg, fluorine atom),
(iii) carboxy,
(iv) alkoxy (eg, methoxy),
(v) cyano,
(vi) nitro, and (vii) mono- or di-alkylamino (eg, dimethylamino)
Aryl (eg, phenyl) optionally substituted with 1 to 3 (preferably 1 or 2) substituents selected from
(m) Non-aromatic heterocyclic group [eg, pyrrolidinyl (eg, 1-pyrrolidinyl), dihydrobenzofuryl (eg, 2,3-dihydrobenzofuran-6-yl), benzodioxanyl (eg, 1,4- Benzodioxan-6-yl), benzodioxolyl (eg 1,3-benzodioxol-5-yl)],
(n) an aromatic heterocyclic group optionally substituted with alkyl (eg, methyl) optionally substituted with 1 to 7 halogen atoms (eg, fluorine atom) [eg, furyl (eg, 2- Furyl), thienyl (eg, 2-thienyl), pyrrolyl (eg, 1-pyrrolyl), thiadiazolyl (eg, 1,3,4-thiadiazol-2-yl), pyridyl (2-pyridyl), triazolyl (eg, 2H) -[1,2,3] -triazol-4-yl), oxazolyl (eg, isoxazol-5-yl)], and (o) aryloxy (eg, phenoxy)
A 5- to 14-membered carbocyclic group optionally substituted with 1 to 3 (preferably 1 or 2) substituents selected from: [eg, phenyl, indanyl (eg, 2-indanyl, 5- Indanyl), naphthyl (eg, 1-naphthyl), fluorenyl (eg, 2-fluorenyl, 9-fluorenyl), cyclopentyl] and the like.

The “biaryl” of the “optionally substituted biaryl” represented by A is preferably biphenylyl, a monovalent substituent in which a 5- or 6-membered aromatic heterocyclic ring and phenyl are directly bonded, or 5 or 6 Monovalent substituents in which member aromatic heterocycles are directly bonded to each other, and more preferably biphenylyl (eg, 4-biphenylyl, 3-biphenylyl, etc.), pyridylphenyl (eg, 2-pyridylphenyl, 3-pyridyl). Phenyl, 4-pyridylphenyl), phenylpyridyl (eg, 2-phenyl-5-pyridyl, 3-phenyl-6-pyridyl) and the like.
In another embodiment, more preferably, biphenylyl (eg, 4-biphenylyl, 3-biphenylyl, etc.), furylphenyl, pyrazolylthiazolyl, thiadiazolylphenyl, phenyloxadiazolyl, thienylphenyl, pyrrolylphenyl] and the like is there.
Furthermore, as another aspect, more preferably biphenylyl (eg, 4-biphenylyl, 3-biphenylyl, etc.), furylphenyl, pyrazolylthiazolyl, thiadiazolylphenyl, phenyloxadiazolyl, thienylphenyl, pyrrolylphenyl, Phenylpyridyl, pyridylphenyl, triazolylphenyl, oxazolylphenyl (eg, isoxazol-5-ylphenyl) and the like.

The “biaryl” may have one or more (preferably 1 to 3, more preferably 1 or 2) substituents at any substitutable position. Examples of such a substituent include the substituent group A described above. When the number of the substituents is 2 or more, these substituents may be the same or different.

The “optionally substituted biaryl” is preferably
(a) a halogen atom (eg, fluorine atom, chlorine atom), and
(b) Alkyl (eg, methyl, isopropyl) optionally substituted with 1 to 7 halogen atoms (eg, fluorine atom)
Biaryl optionally substituted with 1 to 3 (preferably 1 or 2) substituents selected from [eg, biphenylyl (eg, 4-biphenylyl, 3-biphenylyl), furylphenyl, pyrazolylthiazolyl , Thiadiazolylphenyl, phenyloxadiazolyl, thienylphenyl, pyrrolylphenyl].
In another embodiment, the “optionally substituted biaryl” is preferably
(a) a halogen atom (eg, fluorine atom, chlorine atom),
(b) alkyl (eg, methyl, isopropyl) optionally substituted with 1 to 7 halogen atoms (eg, fluorine atom),
(c) carboxy,
(d) alkoxy (eg, methoxy),
(e) cyano,
(f) nitro, and
(g) Mono- or di-alkylamino (eg dimethylamino)
Biaryl optionally substituted with 1 to 3 (preferably 1 or 2) substituents selected from [eg, biphenylyl (eg, 4-biphenylyl, 3-biphenylyl), furylphenyl, pyrazolylthiazolyl , Thiadiazolylphenyl, phenyloxadiazolyl, thienylphenyl, pyrrolylphenyl, phenylpyridyl, pyridylphenyl, triazolylphenyl, oxazolylphenyl (eg, isoxazol-5-ylphenyl)].

The “heterocyclic group” of the “optionally substituted heterocyclic group” represented by A is preferably oxazolyl (eg, 4-oxazolyl), thiazolyl (eg, 2-thiazolyl, 5-thiazolyl), thienyl ( Examples, 2-thienyl), oxadiazolyl (eg, [1,2,4] oxadiazol-5-yl), pyridyl (eg, 2-pyridyl, 3-pyridyl, 4-pyridyl), benzoimidazolyl (eg, 5- Benzimidazolyl), indolyl (eg, 5-indolyl), benzothiazolyl (eg, 2-benzothiazolyl), carbazolyl (eg, 3-carbazolyl, 9-carbazolyl), dihydroindolyl (eg, 2,3-dihydroindol-5-yl) , 2,3-dihydroindol-1-yl), dihydroisoindolyl (eg, 2,3-dihydroisoindol-5) Yl, 2,3-dihydroisoindol-2-yl) and the like.
The “heterocyclic group” of the “optionally substituted heterocyclic group” represented by A is more preferably oxazolyl (eg, 4-oxazolyl), thiazolyl (eg, 2-thiazolyl, 5-thiazolyl), thienyl (Eg, 2-thienyl), oxadiazolyl (eg, [1,2,4] oxadiazol-5-yl), benzimidazolyl (eg, 5-benzoimidazolyl), indolyl (eg, 5-indolyl), dihydroindolyl ( Examples are 2,3-dihydroindol-5-yl, 2,3-dihydroindol-1-yl), benzothiazolyl (eg, 2-benzothiazolyl), carbazolyl (eg, 3-carbazolyl, 9-carbazolyl) and the like.
In another embodiment, the “heterocyclic group” of the “optionally substituted heterocyclic group” is more preferably oxazolyl (eg, 4-oxazolyl), thiazolyl (eg, 2-thiazolyl, 5-thiazolyl), Thienyl (eg, 2-thienyl), oxadiazolyl (eg, [1,2,4] oxadiazol-5-yl), benzimidazolyl (eg, 5-benzimidazolyl), indolyl (eg, 5-indolyl), dihydroindolyl (Eg, 2,3-dihydroindol-5-yl, 2,3-dihydroindol-1-yl), benzothiazolyl (eg, 2-benzothiazolyl), carbazolyl (eg, 3-carbazolyl, 9-carbazolyl), pyridyl ( Examples are 2-pyridyl), benzoxazolyl (eg, 6-benzoxazolyl) and the like.

The “heterocyclic group” may have one or more (preferably 1 to 3, more preferably 1 or 2) substituents at any substitutable position. Examples of such a substituent include the substituent group A described above. When the number of the substituents is 2 or more, these substituents may be the same or different.

The “optionally substituted heterocyclic group” is preferably
(a) alkyl (eg, methyl, ethyl, isopropyl),
(b) alkenyl (eg, 4-methyl-1-pentenyl),
(c) alkylcarbonyl (eg, acetyl),
(d) aryl (eg, phenyl), and
(e) Aromatic heterocyclic group (eg, pyrazolyl)
5- to 14-membered heterocyclic group optionally substituted with 1 to 3 (preferably 1 or 2) substituents selected from [eg, oxazolyl (eg, 4-oxazolyl), thiazolyl (eg, , 2-thiazolyl, 5-thiazolyl), thienyl (eg, 2-thienyl), oxadiazolyl (eg, [1,2,4] oxadiazol-5-yl), benzoimidazolyl (eg, 5-benzoimidazolyl), indolyl ( Example, 5-indolyl), dihydroindolyl (eg, 2,3-dihydroindol-5-yl, 2,3-dihydroindol-1-yl), benzothiazolyl (eg, 2-benzothiazolyl), carbazolyl (eg, 3) -Carbazolyl, 9-carbazolyl)].

A is preferably an optionally substituted 6-14 membered carbocyclic group, an optionally substituted biaryl, or an optionally substituted 5-14 membered heterocyclic group, specifically Is
(1) (a) a halogen atom (eg, chlorine atom),
(b) Nitro,
(c) alkyl (eg, methyl, isopropyl, tert-butyl, hexyl) optionally substituted with 1 to 5 halogen atoms (eg, fluorine atom),
(d) alkenyl (eg, 2-methyl-1-propenyl, 4-methyl-1-pentenyl, 5-methyl-1-hexenyl),
(e) arylalkenyl [eg, phenyl vinyl (eg, 2-phenyl vinyl)],
(f) alkynyl (eg, ethynyl),
(g) arylalkynyl (eg, phenylethynyl),
(h) heterocyclic alkynyl [eg, thiazolylethynyl (eg, thiazol-5-ylethynyl)],
(i) alkoxy (eg, isopropoxy),
(j) mono- or di-alkylamino (eg ethylamino, dimethylamino, diethylamino),
(k) cycloalkyl (eg, cyclopropyl),
(l) (i) a halogen atom (eg, fluorine atom, chlorine atom), and (ii) an alkyl optionally substituted with 1 to 7 halogen atoms (eg, fluorine atom) (eg, methyl, isopropyl)
Aryl (eg, phenyl) optionally substituted with 1 to 3 (preferably 1 or 2) substituents selected from
(m) a non-aromatic heterocyclic group [eg, pyrrolidinyl (eg, 1-pyrrolidinyl)], and (n) an aromatic heterocyclic group [eg, furyl (eg, 2-furyl), thienyl (eg, 2-thienyl) ), Pyrrolyl (eg, 1-pyrrolyl), thiadiazolyl (eg, 1,3,4-thiadiazol-2-yl)]
6- to 14-membered carbocyclic group which may be substituted with 1 to 3 (preferably 1 or 2) substituents selected from [eg, phenyl, indanyl (eg, 2-indanyl, 5- Indanyl), naphthyl (eg, 1-naphthyl), fluorenyl (eg, 2-fluorenyl)],
(2) (a) a halogen atom (eg, fluorine atom, chlorine atom), and (b) an alkyl optionally substituted with 1 to 7 halogen atoms (eg, fluorine atom) (eg, methyl, isopropyl)
Biaryl optionally substituted with 1 to 3 (preferably 1 or 2) substituents selected from [eg, biphenylyl (eg, 4-biphenylyl, 3-biphenylyl), furylphenyl, pyrazolylthiazolyl , Thiadiazolylphenyl, phenyloxadiazolyl, thienylphenyl, pyrrolylphenyl],
(3) (a) alkyl (eg, methyl, ethyl, isopropyl),
(b) alkenyl (eg, 4-methyl-1-pentenyl),
(c) alkylcarbonyl (eg, acetyl),
(d) aryl (eg, phenyl), and (e) aromatic heterocyclic group (eg, pyrazolyl)
5- to 14-membered heterocyclic group optionally substituted with 1 to 3 (preferably 1 or 2) substituents selected from [eg, oxazolyl (eg, 4-oxazolyl), thiazolyl (eg, , 2-thiazolyl, 5-thiazolyl), thienyl (eg, 2-thienyl), oxadiazolyl (eg, [1,2,4] oxadiazol-5-yl), benzoimidazolyl (eg, 5-benzoimidazolyl), indolyl ( Example, 5-indolyl), dihydroindolyl (eg, 2,3-dihydroindol-5-yl, 2,3-dihydroindol-1-yl), benzothiazolyl (eg, 2-benzothiazolyl), carbazolyl (eg, 3) -Carbazolyl, 9-carbazolyl)].

In another embodiment, A is preferably an optionally substituted 6-14 membered carbocyclic group, an optionally substituted biaryl, or an optionally substituted 5-14 membered heterocyclic group. Yes, specifically A is
(1) (a) a halogen atom (eg, chlorine atom),
(b) Nitro,
(c) alkyl (eg, methyl, isopropyl, tert-butyl, hexyl) optionally substituted with 1 to 5 halogen atoms (eg, fluorine atom),
(d) alkenyl (eg, 2-methyl-1-propenyl, 4-methyl-1-pentenyl, 5-methyl-1-hexenyl),
(e) arylalkenyl [eg, phenyl vinyl (eg, 2-phenyl vinyl)],
(f) alkynyl (eg, ethynyl),
(g) arylalkynyl (eg, phenylethynyl),
(h) heterocyclic alkynyl [eg, thiazolylethynyl (eg, thiazol-5-ylethynyl)],
(i) alkoxy (eg, methoxy, isopropoxy),
(j) mono- or di-alkylamino (eg ethylamino, dimethylamino, diethylamino),
(k) cycloalkyl (eg, cyclobutyl),
(l) (i) a halogen atom (eg, fluorine atom, chlorine atom),
(ii) alkyl (eg, methyl, isopropyl) optionally substituted with 1 to 7 halogen atoms (eg, fluorine atom),
(iii) carboxy,
(iv) alkoxy (eg, methoxy),
(v) cyano,
(vi) nitro, and (vi) mono- or di-alkylamino (eg, dimethylamino)
Aryl (eg, phenyl) optionally substituted with 1 to 3 (preferably 1 or 2) substituents selected from
(m) Non-aromatic heterocyclic group [eg, pyrrolidinyl (eg, 1-pyrrolidinyl), dihydrobenzofuryl (eg, 2,3-dihydrobenzofuran-6-yl), benzodioxanyl (eg, 1,4- Benzodioxan-6-yl), benzodioxolyl (eg 1,3-benzodioxol-5-yl)],
(n) an aromatic heterocyclic group optionally substituted with alkyl (eg, methyl) optionally substituted with 1 to 7 halogen atoms (eg, fluorine atom) [eg, furyl (eg, 2- Furyl), thienyl (eg, 2-thienyl), pyrrolyl (eg, 1-pyrrolyl), thiadiazolyl (eg, 1,3,4-thiadiazol-2-yl), pyridyl (2-pyridyl), triazolyl (eg, 2H) -[1,2,3] -triazol-4-yl), oxazolyl (eg, isoxazol-5-yl)], and (o) aryloxy (eg, phenoxy)
A 5- to 14-membered carbocyclic group optionally substituted with 1 to 3 (preferably 1 or 2) substituents selected from: [eg, phenyl, indanyl (eg, 2-indanyl, 5- Indanyl), naphthyl (eg, 1-naphthyl), fluorenyl (eg, 2-fluorenyl, 9-fluorenyl), cyclopentyl],
(2) (a) a halogen atom (eg, fluorine atom, chlorine atom),
(b) alkyl (eg, methyl, isopropyl) optionally substituted with 1 to 7 halogen atoms (eg, fluorine atom),
(c) carboxy,
(d) alkoxy (eg, methoxy),
(e) cyano,
(f) nitro, and (g) mono- or di-alkylamino (eg, dimethylamino)
Biaryl optionally substituted with 1 to 3 (preferably 1 or 2) substituents selected from [eg, biphenylyl (eg, 4-biphenylyl, 3-biphenylyl), furylphenyl, pyrazolylthiazolyl , Thiadiazolylphenyl, phenyloxadiazolyl, thienylphenyl, pyrrolylphenyl, phenylpyridyl, pyridylphenyl, triazolylphenyl, oxazolylphenyl (eg, isoxazol-5-ylphenyl)],
(3) (a) alkyl (eg, methyl, ethyl, isopropyl),
(b) alkenyl (eg, 4-methyl-1-pentenyl),
(c) alkylcarbonyl (eg, acetyl),
(d) aryl (eg, phenyl), and (e) aromatic heterocyclic group (eg, pyrazolyl)
5- to 14-membered heterocyclic group optionally substituted with 1 to 3 (preferably 1 or 2) substituents selected from [eg, oxazolyl (eg, 4-oxazolyl), thiazolyl (eg, , 2-thiazolyl, 5-thiazolyl), thienyl (eg, 2-thienyl), oxadiazolyl (eg, [1,2,4] oxadiazol-5-yl), benzoimidazolyl (eg, 5-benzoimidazolyl), indolyl ( Example, 5-indolyl), dihydroindolyl (eg, 2,3-dihydroindol-5-yl, 2,3-dihydroindol-1-yl), benzothiazolyl (eg, 2-benzothiazolyl), carbazolyl (eg, 3) -Carbazolyl, 9-carbazolyl), pyridyl (eg, 2-pyridyl)].

A is more preferably an optionally substituted phenyl or an optionally substituted dihydroindolyl (eg, 2,3-dihydroindol-5-yl, 2,3-dihydroindol-1-yl). Yes, specifically,
(1) (a) a halogen atom (eg, chlorine atom),
(b) Nitro,
(c) alkyl (eg, methyl, isopropyl, tert-butyl, hexyl) optionally substituted with 1 to 5 halogen atoms (eg, fluorine atom),
(d) alkenyl (eg, 2-methyl-1-propenyl, 4-methyl-1-pentenyl, 5-methyl-1-hexenyl),
(e) arylalkenyl [eg, phenyl vinyl (eg, 2-phenyl vinyl)],
(f) alkynyl (eg, ethynyl),
(g) arylalkynyl (eg, phenylethynyl),
(h) heterocyclic alkynyl [eg, thiazolylethynyl (eg, thiazol-5-ylethynyl)],
(i) alkoxy (eg, isopropoxy),
(j) mono- or di-alkylamino (eg ethylamino, dimethylamino, diethylamino),
(k) cycloalkyl (eg, cyclobutyl),
(l) (i) a halogen atom (eg, fluorine atom, chlorine atom), and (ii) an alkyl optionally substituted with 1 to 7 halogen atoms (eg, fluorine atom) (eg, methyl, isopropyl)
Aryl (eg, phenyl) optionally substituted with 1 to 3 (preferably 1 or 2) substituents selected from
(m) a non-aromatic heterocyclic group [eg, pyrrolidinyl (eg, 1-pyrrolidinyl)], and (n) an aromatic heterocyclic group [eg, furyl (eg, 2-furyl), thienyl (eg, 2-thienyl) ), Pyrrolyl (eg, 1-pyrrolyl), thiadiazolyl (eg, 1,3,4-thiadiazol-2-yl)]
Phenyl optionally substituted with 1 to 3 (preferably 1 or 2) substituents selected from: or (2) (a) alkyl (eg, methyl, ethyl, isopropyl), and (b ) Alkylcarbonyl (eg, acetyl)
Dihydroindolyl (eg, 2,3-dihydroindol-5-yl, 2,3-dihydroindole-1) optionally substituted with 1 to 3 (preferably 1) substituents selected from -Il).

In another embodiment, A is more preferably an optionally substituted carbocyclic group or an optionally substituted heterocyclic group, specifically,
(1) (a) alkyl (eg, isopropyl, hexyl), and (b) mono- or di-alkylamino (eg, ethylamino, dimethylamino, diethylamino)
6- to 14-membered carbocyclic group optionally substituted by 1 to 3 (preferably 1 or 2) substituents selected from [eg, phenyl, indanyl (eg, 2-indanyl, 5- Indanyl)], or (2) (a) alkyl (eg, methyl, ethyl, isopropyl), and (b) alkylcarbonyl (eg, acetyl)
5- to 14-membered heterocyclic group optionally substituted with 1 to 3 (preferably 1 or 2) substituents selected from [eg, thienyl (eg, 2-thienyl), benzoimidazolyl (eg, , 5-benzimidazolyl), dihydroindolyl (eg, 2,3-dihydroindol-5-yl)].
Furthermore, in another aspect, A is more preferably
(1) (a) alkyl (eg, isopropyl, hexyl),
(b) mono- or di-alkylamino (eg ethylamino, dimethylamino, diethylamino),
(c) (i) alkyl (eg, methyl) optionally substituted with 1 to 7 halogen atoms (eg, fluorine atom),
(ii) Nitro,
(iii) mono- or di-alkylamino (eg, dimethylamino), and (iv) alkoxy (eg, methoxy)
Aryl (eg, phenyl) optionally substituted with 1 to 3 substituents selected from: (d) a non-aromatic heterocyclic group [eg, benzodioxanyl (eg, 1,4-benzo Dioxane-6-yl)]
6- to 14-membered carbocyclic group optionally substituted by 1 to 3 (preferably 1 or 2) substituents selected from [eg, phenyl, indanyl (eg, 2-indanyl, 5- Indanyl)], or (2) (a) alkyl (eg, methyl, ethyl, isopropyl), and (b) alkylcarbonyl (eg, acetyl)
5- to 14-membered heterocyclic group optionally substituted with 1 to 3 (preferably 1 or 2) substituents selected from [eg, thienyl (eg, 2-thienyl), benzoimidazolyl (eg, , 5-benzimidazolyl), dihydroindolyl (eg, 2,3-dihydroindol-5-yl)].

A is more preferably an optionally substituted aryl, an optionally substituted biaryl, or an optionally substituted aromatic heterocyclic group, specifically,
(1) (a) a halogen atom (eg, chlorine atom),
(b) Nitro,
(c) alkyl (eg, isopropyl, tert-butyl),
(d) alkenyl (eg, 2-methyl-1-propenyl, 4-methyl-1-pentenyl, 5-methyl-1-hexenyl),
(e) arylalkenyl [eg, phenyl vinyl (eg, 2-phenyl vinyl)],
(f) alkynyl (eg, ethynyl),
(g) heterocyclic alkynyl [eg, thiazoleethynyl (eg, thiazol-5-ylethynyl)],
(h) arylalkynyl (eg, phenylethynyl),
(i) alkoxy (eg, isopropoxy),
(j) cycloalkyl (eg, cyclobutyl),
(k) (i) a halogen atom (eg, fluorine atom, chlorine atom), and (ii) an alkyl optionally substituted with 1 to 3 halogen atoms (eg, fluorine atom) (eg, methyl)
Aryl (eg, phenyl) optionally substituted with 1 to 3 (preferably 1 or 2) substituents selected from
(l) non-aromatic heterocyclic group [eg, pyrrolidinyl (eg, 1-pyrrolidinyl)], and (m) aromatic heterocyclic group [eg, furyl (eg, 2-furyl), thienyl (eg, 2-thienyl) ), Pyrrolyl (eg, 1-pyrrolyl), thiadiazolyl (eg, 1,3,4-thiadiazol-2-yl)]
C _6-10 aryl optionally substituted by 1 to 3 (preferably 1 or 2) substituents selected from [eg, phenyl, naphthyl (eg, 1-naphthyl)],
(2) (a) a halogen atom (eg, fluorine atom, chlorine atom), and (b) an alkyl optionally substituted with 1 to 7 halogen atoms (eg, fluorine atom) (eg, methyl, isopropyl)
Biaryl optionally substituted with 1 to 3 (preferably 1 or 2) substituents selected from [eg, biphenylyl (eg, 4-biphenylyl), pyrazolylthiazolyl, thiadiazolylphenyl, Phenyloxadiazolyl, thienylphenyl, pyrrolylphenyl, furylphenyl], or (3) (a) alkyl (eg, methyl, isopropyl),
(b) alkenyl (eg, 4-methyl-1-pentenyl),
(c) aryl (eg, phenyl), and (d) aromatic heterocyclic group (eg, pyrazolyl)
5- to 14-membered aromatic heterocyclic group optionally substituted by 1 to 3 (preferably 1 or 2) substituents selected from [eg, oxazolyl (eg, 4-oxazolyl), thiazolyl (Eg, 2-thiazolyl, 5-thiazolyl), thienyl (eg, 2-thienyl), oxadiazolyl (eg, [1,2,4] oxadiazol-5-yl), benzothiazolyl (eg, 2-benzothiazolyl)] It is.
In another embodiment, A is more preferably an optionally substituted aryl, an optionally substituted biaryl, or an optionally substituted aromatic heterocyclic group, specifically,
(1) (a) a halogen atom (eg, chlorine atom),
(b) Nitro,
(c) alkyl (eg, isopropyl, tert-butyl),
(d) alkenyl (eg, 2-methyl-1-propenyl, 4-methyl-1-pentenyl, 5-methyl-1-hexenyl),
(e) arylalkenyl [eg, phenyl vinyl (eg, 2-phenyl vinyl)],
(f) alkynyl (eg, ethynyl),
(g) heterocyclic alkynyl [eg, thiazoleethynyl (eg, thiazol-5-ylethynyl)],
(h) arylalkynyl (eg, phenylethynyl),
(i) alkoxy (eg, methoxy, isopropoxy),
(j) cycloalkyl (eg, cyclobutyl),
(k) (i) a halogen atom (eg, fluorine atom, chlorine atom),
(ii) alkyl (eg, methyl) optionally substituted with 1 to 3 halogen atoms (eg, fluorine atom),
(iii) carboxy,
(iv) alkoxy (eg, methoxy),
(v) cyano,
(vi) nitro, and (vii) mono- or di-alkylamino (eg, dimethylamino)
Aryl (eg, phenyl) optionally substituted with 1 to 3 (preferably 1 or 2) substituents selected from
(l) Non-aromatic heterocyclic group [eg, pyrrolidinyl (eg, 1-pyrrolidinyl), dihydrobenzofuryl (eg, 2,3-dihydrobenzofuran-6-yl), benzodioxanyl (eg, 1,4- Benzodioxan-6-yl), benzodioxolyl (eg 1,3-benzodioxol-5-yl)],
(m) an aromatic heterocyclic group optionally substituted with alkyl (eg, methyl) optionally substituted with 1 to 7 halogen atoms (eg, fluorine atom) [eg, furyl (eg, 2- Furyl), thienyl (eg, 2-thienyl), pyrrolyl (eg, 1-pyrrolyl), thiadiazolyl (eg, 1,3,4-thiadiazol-2-yl), pyridyl (eg, 2-pyridyl), triazolyl (eg, 2H- [1,2,3] -triazol-4-yl), oxazolyl (eg, isoxazol-5-yl)], and (n) aryloxy (eg, phenoxy)
C _6-10 aryl optionally substituted with 1 to 3 (preferably 1 or 2) substituents selected from [eg, phenyl, naphthyl (eg, 1-naphthyl)],
(2) (a) a halogen atom (eg, fluorine atom, chlorine atom),
(b) alkyl (eg, methyl, isopropyl) optionally substituted with 1 to 7 halogen atoms (eg, fluorine atom),
(c) carboxy,
(d) alkoxy (eg, methoxy),
(e) cyano,
(f) nitro, and (g) mono- or di-alkylamino (eg, dimethylamino)
Biaryl optionally substituted with 1 to 3 (preferably 1 or 2) substituents selected from [eg, biphenylyl (eg, 4-biphenylyl), pyrazolylthiazolyl, thiadiazolylphenyl, Phenyloxadiazolyl, thienylphenyl, pyrrolylphenyl, furylphenyl, phenylpyridyl, pyridylphenyl, triazolylphenyl, oxazolylphenyl (eg, isoxazol-5-ylphenyl)],
(3) (a) alkyl (eg, methyl, isopropyl),
(b) alkenyl (eg, 4-methyl-1-pentenyl),
(c) aryl (eg, phenyl), and (d) aromatic heterocyclic group (eg, pyrazolyl)
5- to 14-membered aromatic heterocyclic group optionally substituted by 1 to 3 (preferably 1 or 2) substituents selected from [eg, oxazolyl (eg, 4-oxazolyl), thiazolyl (Eg, 2-thiazolyl, 5-thiazolyl), thienyl (eg, 2-thienyl), oxadiazolyl (eg, [1,2,4] oxadiazol-5-yl), benzothiazolyl (eg, 2-benzothiazolyl), Pyridyl (eg, 2-pyridyl), benzoxazolyl (eg, 6-benzoxazolyl)].

A is even more preferably an optionally substituted phenyl, specifically
(1) (a) a halogen atom (eg, chlorine atom),
(b) Nitro,
(c) alkyl (eg, methyl, isopropyl, tert-butyl) optionally substituted with 1 to 3 halogen atoms (eg, fluorine atom),
(d) alkenyl (eg, 2-methyl-1-propenyl, 4-methyl-1-pentenyl, 5-methyl-1-hexenyl),
(e) arylalkenyl [eg, phenyl vinyl (eg, 2-phenyl vinyl)],
(f) alkynyl (eg, ethynyl),
(g) heterocyclic alkynyl [eg, thiazolylethynyl (eg, thiazol-5-ylethynyl)],
(h) arylalkynyl (eg, phenylethynyl),
(i) alkoxy (eg, isopropoxy),
(j) cycloalkyl (eg, cyclobutyl),
(k) (i) a halogen atom (eg, fluorine atom, chlorine atom), and (ii) an alkyl optionally substituted with 1 to 3 halogen atoms (eg, fluorine atom) (eg, methyl, isopropyl)
Aryl (eg, phenyl) optionally substituted with 1 to 3 substituents selected from
(l) non-aromatic heterocyclic group [eg, pyrrolidinyl (eg, 1-pyrrolidinyl)], and (m) aromatic heterocyclic group [eg, furyl (eg, 2-furyl), thienyl (eg, 2-thienyl) ), Pyrrolyl (eg, 1-pyrrolyl), thiadiazolyl (eg, 1,3,4-thiadiazol-2-yl)]
It is phenyl optionally substituted by 1 to 3 (preferably 1 or 2) substituents selected from
In another aspect, A is even more preferably an optionally substituted phenyl, specifically
(1) (a) a halogen atom (eg, chlorine atom),
(b) Nitro,
(c) alkyl (eg, isopropyl, tert-butyl),
(d) alkenyl (eg, 2-methyl-1-propenyl, 4-methyl-1-pentenyl, 5-methyl-1-hexenyl),
(e) arylalkenyl [eg, phenyl vinyl (eg, 2-phenyl vinyl)],
(f) alkynyl (eg, 1-propynyl),
(g) heterocyclic alkynyl [eg, thiazoleethynyl (eg, thiazol-5-ylethynyl)],
(h) arylalkynyl (eg, phenylethynyl),
(i) alkoxy (eg, methoxy, isopropoxy),
(j) cycloalkyl (eg, cyclobutyl),
(k) (i) a halogen atom (eg, fluorine atom, chlorine atom),
(ii) Alkyl (eg, methyl) optionally substituted with 1 to 3 halogen atoms (eg, fluorine atom)
(iii) carboxy,
(iv) alkoxy (eg, methoxy),
(v) cyano,
(vi) nitro, and (vii) mono- or di-alkylamino (eg, dimethylamino)
Aryl (eg, phenyl) optionally substituted with 1 to 3 substituents selected from
(l) Non-aromatic heterocyclic group [eg, pyrrolidinyl (eg, 1-pyrrolidinyl), dihydrobenzofuryl (eg, 2,3-dihydrobenzofuran-6-yl), benzodioxolyl (eg, 1,3- Benzodioxol-5-yl)],
(m) an aromatic heterocyclic group optionally substituted with alkyl (eg, methyl) optionally substituted with 1 to 7 halogen atoms (eg, fluorine atom) [eg, furyl (eg, 2- Furyl), thienyl (eg, 2-thienyl), pyrrolyl (eg, 1-pyrrolyl), thiadiazolyl (eg, 1,3,4-thiadiazol-2-yl), pyridyl (eg, 2-pyridyl), triazolyl (eg, 2H- [1,2,3] triazol-4-yl), oxazolyl (eg, isoxazol-5-yl)], and (n) aryloxy (eg, phenoxy)
It is phenyl optionally substituted by 1 to 3 (preferably 1 or 2) substituents selected from

B represents a divalent carbocyclic group that may be substituted, a biarylene that may be substituted, or a divalent heterocyclic group that may be substituted.

The “divalent carbocyclic group” of the “optionally substituted divalent carbocyclic group” represented by B is preferably a C _6-10 arylene or a divalent non-aromatic carbocyclic group, More preferably, phenylene (eg, 1,4-phenylene, 1,3-phenylene, 1,2-phenylene), indan-diyl (eg, indan-2,5-diyl), naphthylene (eg, 1,5-phenylene) Naphthylene).
The “divalent carbocyclic group” may have one or more (preferably 1 to 3, more preferably 1 or 2) substituents at any substitutable position. Examples of such a substituent include the substituent group A described above. When the number of the substituents is 2 or more, these substituents may be the same or different.

The “optionally substituted divalent carbocyclic group” is preferably
(a) a halogen atom (eg, a chlorine atom),
(b) alkoxy (eg, methoxy),
(c) aryloxy (eg, phenoxy), and
(d) arylalkoxyalkyl (eg, benzyloxymethyl) optionally substituted with alkyl (eg, isopropyl)
C _6-10 arylene optionally substituted with 1 to 3 (preferably 1) substituents selected from [eg, phenylene (eg, 1,4-phenylene, 1,2-phenylene), Indan-diyl (eg, indan-2,5-diyl), naphthylene (eg, 1,5-naphthylene)].

The “biarylene” of the “optionally substituted biarylene” represented by B is preferably biphenylylene, phenylpyridine-diyl, phenylpyrazole-diyl, phenylpyridazine-diyl, pyrazolylpyridazine-diyl.
The “biarylene” may have one or more (preferably 1 to 3, more preferably 1 or 2) substituents at any substitutable position. Examples of such a substituent include the substituent group A described above. When the number of the substituents is 2 or more, these substituents may be the same or different.
The “optionally substituted biarylene” represented by B is preferably “biarylene”, more preferably biphenylylene (eg, 4,4′-biphenylylene, 2,4′-biphenylylene), phenylpyridine- Diyl, phenylpyrazole-diyl, phenylpyridazine-diyl, pyrazolylpyridazine-diyl.

The “divalent heterocyclic group” of the “optionally substituted divalent heterocyclic group” represented by B is preferably thiophene-diyl, oxadiazole-diyl, pyridine-diyl, pyridazine-diyl, Benzofuran-diyl, indole-diyl, benzimidazole-diyl, dihydroindole-diyl, quinoline-diyl.
The “divalent heterocyclic group” may have one or more (preferably 1 to 3, more preferably 1 or 2) substituents at any substitutable position. Examples of such a substituent include the substituent group A described above. When the number of the substituents is 2 or more, these substituents may be the same or different.

In another embodiment, the “divalent heterocyclic group” of the “optionally substituted divalent heterocyclic group” represented by B is preferably thiophene-diyl, oxadiazole-diyl, pyridine-diyl. Pyridazine-diyl, benzofuran-diyl, indole-diyl, benzimidazole-diyl, dihydroindole-diyl, quinoline-diyl, pyrrole-diyl.
The “divalent heterocyclic group” may have one or more (preferably 1 to 3, more preferably 1 or 2) substituents at any substitutable position. Examples of such a substituent include the substituent group A described above. When the number of the substituents is 2 or more, these substituents may be the same or different.

The “optionally substituted divalent heterocyclic group” is preferably a divalent heterocyclic group, more preferably thiophene-diyl (eg, thiophene-2,5-diyl), oxadi Azole-diyl (eg, [1,2,4] oxadiazole-3,5-diyl), pyridine-diyl (eg, pyridine-2,5-diyl), pyridazine-diyl (eg, pyridazine-3,6) -Diyl), benzofuran-diyl (eg, benzofuran-2,5-diyl, benzofuran-2,6-diyl), indole-diyl (eg, indole-2,6-diyl), benzimidazole-diyl (eg, benzo Imidazole-2,5-diyl), dihydroindole-diyl (eg, 2,3-dihydroindole-1,5-diyl), quinoline-diyl (eg, quinoline-3,7-di) Le, a quinoline-5,8-diyl).

In another embodiment, the “optionally substituted divalent heterocyclic group” is preferably a divalent heterocyclic group, more preferably thiophene-diyl (eg, thiophene-2,5- Diyl), oxadiazole-diyl (eg, [1,2,4] oxadiazole-3,5-diyl), pyridine-diyl (eg, pyridine-2,5-diyl), pyridazine-diyl (eg, Pyridazine-3,6-diyl), benzofuran-diyl (eg, benzofuran-2,5-diyl, benzofuran-2,6-diyl), indole-diyl (eg, indole-2,6-diyl), benzimidazole- Diyl (eg, benzimidazol-2,5-diyl), dihydroindole-diyl (eg, 2,3-dihydroindole-1,5-diyl), quinoline-diyl (eg, quino) Down-3,7-diyl, quinoline-5,8-diyl), pyrrole - diyl (e.g., pyrrole-1,3-diyl).

Here, “2 of the optionally substituted divalent carbocyclic group”, “optionally substituted biarylene”, and “optionally substituted divalent heterocyclic group” represented by B are “2”. Either of the two bonds of “valent carbocyclic group”, “biarylene” and “divalent heterocyclic group” may be bonded to X.
For example, in the “divalent heterocyclic group” of the “optionally substituted divalent heterocyclic group” represented by B, “benzofuran-2,5-diyl”

(Wherein, * represents a bonding position with X, and ** represents a bonding position with Y). The same applies to other cases.

B is preferably a divalent carbocyclic group that may be substituted, a biarylene that may be substituted, or a divalent heterocyclic group that may be substituted. Specifically,
(1) (a) a halogen atom (eg, chlorine atom),
(b) alkoxy (eg, methoxy),
(c) aryloxy (eg, phenoxy), and (d) arylalkoxyalkyl optionally substituted with alkyl (eg, isopropyl) (eg, benzyloxymethyl)
A divalent carbocyclic group which may be substituted by 1 to 3 (preferably 1) substituents selected from [eg, phenylene (eg, 1,4-phenylene, 1,2-phenylene) , Indan-diyl (eg, indan-2,5-diyl), naphthylene (eg, 1,5-naphthylene)],
(2) Biarylene [eg, biphenylylene (eg, 4,4′-biphenylylene, 2,4′-biphenylylene), phenylpyridine-diyl, phenylpyrazole-diyl, phenylpyridazine-diyl, pyrazolylpyridazine-diyl], or (3 ) Divalent heterocyclic groups [eg, thiophene-diyl (eg, thiophene-2,5-diyl), oxadiazole-diyl (eg, [1,2,4] oxadiazole-3,5-diyl) , Pyridine-diyl (eg, pyridine-2,5-diyl), pyridazine-diyl (eg, pyridazine-3,6-diyl), benzofuran-diyl (eg, benzofuran-2,5-diyl, benzofuran-2,6) -Diyl), indole-diyl (eg, indole-2,6-diyl), benzimidazole-diyl (eg, benzimidazole) -2,5-diyl), dihydroindole-diyl (eg, 2,3-dihydroindole-1,5-diyl), quinoline-diyl (eg, quinoline-3,7-diyl, quinoline-5,8-) Gille)]
It is.

In another embodiment, B is preferably a divalent carbocyclic group that may be substituted, a biarylene that may be substituted, or a divalent heterocyclic group that may be substituted. Is
(1) (a) a halogen atom (eg, chlorine atom),
(b) alkoxy (eg, methoxy),
(c) aryloxy (eg, phenoxy), and (d) arylalkoxyalkyl optionally substituted with alkyl (eg, isopropyl) (eg, benzyloxymethyl)
A divalent carbocyclic group optionally substituted by 1 to 3 (preferably 1) substituents selected from [eg, phenylene (eg, 1,4-phenylene, 1,3-phenylene, 1,2-phenylene), indan-diyl (eg, indan-2,5-diyl), naphthylene (eg, 1,5-naphthylene)],
(2) Biarylene [eg, biphenylylene (eg, 4,4′-biphenylylene, 2,4′-biphenylylene), phenylpyridine-diyl, phenylpyrazole-diyl, phenylpyridazine-diyl, pyrazolylpyridazine-diyl], or (3 ) Divalent heterocyclic groups [eg, thiophene-diyl (eg, thiophene-2,5-diyl), oxadiazole-diyl (eg, [1,2,4] oxadiazole-3,5-diyl) , Pyridine-diyl (eg, pyridine-2,5-diyl), pyridazine-diyl (eg, pyridazine-3,6-diyl), benzofuran-diyl (eg, benzofuran-2,5-diyl, benzofuran-2,6) -Diyl), indole-diyl (eg, indole-2,6-diyl), benzimidazole-diyl (eg, benzimidazole) -2,5-diyl), dihydroindole-diyl (eg, 2,3-dihydroindole-1,5-diyl), quinoline-diyl (eg, quinoline-3,7-diyl, quinoline-5,8-) Diyl), pyrrole-diyl (eg, pyrrole-1,3-diyl)]
It is.

B is more preferably an optionally substituted divalent 6 to 10-membered carbocyclic group or an optionally substituted divalent 5 to 14-membered heterocyclic group. Specifically,
(1) (a) a halogen atom (eg, chlorine atom),
(b) alkoxy (eg, methoxy),
(c) aryloxy (eg, phenoxy), and (d) arylalkoxyalkyl optionally substituted with alkyl (eg, isopropyl) (eg, benzyloxymethyl)
A divalent 6 to 10-membered carbocyclic group which may be substituted with 1 to 3 (preferably 1) substituents selected from [eg, phenylene (eg, 1,4-phenylene, 1 , 3-phenylene, 1,2-phenylene), indan-diyl (eg, indan-2,5-diyl), naphthylene (eg, 1,5-naphthylene)], or (2) divalent 5- to 14-membered Heterocyclic groups [eg, thiophene-diyl (eg, thiophene-2,5-diyl), oxadiazole-diyl (eg, [1,2,4] oxadiazole-3,5-diyl), pyridine- Diyl (eg, pyridine-2,5-diyl), pyridazine-diyl (eg, pyridazine-3,6-diyl), benzofuran-diyl (eg, benzofuran-2,5-diyl, benzofuran-2,6-diyl) , Indole-diyl (eg, Ndol-2,6-diyl), benzimidazole-diyl (eg, benzimidazol-2,5-diyl), dihydroindole-diyl (eg, 2,3-dihydroindole-1,5-diyl), quinoline-diyl (Eg, quinoline-3,7-diyl, quinoline-5,8-diyl)].

In another embodiment, B is more preferably an optionally substituted divalent 6 to 10 membered carbocyclic group or an optionally substituted divalent 5 to 14 membered heterocyclic group, In particular,
(1) (a) a halogen atom (eg, chlorine atom),
(b) alkoxy (eg, methoxy),
(c) aryloxy (eg, phenoxy), and (d) arylalkoxyalkyl optionally substituted with alkyl (eg, isopropyl) (eg, benzyloxymethyl)
A divalent 6 to 10-membered carbocyclic group which may be substituted with 1 to 3 (preferably 1) substituents selected from [eg, phenylene (eg, 1,4-phenylene, 1 , 3-phenylene, 1,2-phenylene), indan-diyl (eg, indan-2,5-diyl), naphthylene (eg, 1,5-naphthylene)], or (2) divalent 5- to 14-membered Heterocyclic groups [eg, thiophene-diyl (eg, thiophene-2,5-diyl), oxadiazole-diyl (eg, [1,2,4] oxadiazole-3,5-diyl), pyridine- Diyl (eg, pyridine-2,5-diyl), pyridazine-diyl (eg, pyridazine-3,6-diyl), benzofuran-diyl (eg, benzofuran-2,5-diyl, benzofuran-2,6-diyl) , Indole-diyl (eg, Ndol-2,6-diyl), benzimidazole-diyl (eg, benzimidazol-2,5-diyl), dihydroindole-diyl (eg, 2,3-dihydroindole-1,5-diyl), quinoline-diyl (Eg, quinoline-3,7-diyl, quinoline-5,8-diyl), pyrrole-diyl (eg, pyrrole-1,3-diyl)]
It is.

In another embodiment, B is more preferably an optionally substituted arylene, specifically C _6-14 arylene [eg, phenylene (eg, 1,4-phenylene)].

In still another aspect, B is more preferably an optionally substituted arylene or an optionally substituted divalent aromatic heterocyclic group, specifically,
(1) (a) a halogen atom (eg, chlorine atom),
(b) alkoxy (eg, methoxy), and (c) aryloxy (eg, phenoxy)
C _6-10 arylene optionally substituted with 1 to 3 (preferably 1) substituents selected from [eg, phenylene (eg, 1,4-phenylene, 1,3-phenylene)] Or (2) a divalent aromatic heterocyclic group [eg, oxadiazole-diyl (eg, [1,2,4] oxadiazole-3,5-diyl), pyridazine-diyl (eg, pyridazine- 3,6-diyl), thiophene-diyl (eg, thiophene-2,5-diyl)].
In still another aspect, B is more preferably an optionally substituted arylene or an optionally substituted divalent aromatic heterocyclic group, specifically,
(1) (a) a halogen atom (eg, chlorine atom),
(b) alkoxy (eg, methoxy), and (c) aryloxy (eg, phenoxy)
C _6-10 arylene optionally substituted with 1 to 3 (preferably 1) substituents selected from [eg, phenylene (eg, 1,4-phenylene, 1,3-phenylene)] Or (2) a divalent aromatic heterocyclic group [eg, oxadiazole-diyl (eg, [1,2,4] oxadiazole-3,5-diyl), pyridazine-diyl (eg, pyridazine- 3,6-diyl), thiophene-diyl (eg, thiophene-2,5-diyl), pyridine-diyl (eg, pyridine-2,5-diyl)].

B is more preferably an optionally substituted phenylene or an optionally substituted benzofuranylene, specifically,
(1) (a) a halogen atom (eg, chlorine atom),
(b) alkoxy (eg, methoxy),
(c) aryloxy (eg, phenoxy), and (d) arylalkoxyalkyl optionally substituted with alkyl (eg, isopropyl) (eg, benzyloxymethyl)
Phenylene (eg, 1,4-phenylene, 1,3-phenylene, 1,2-phenylene) optionally substituted with 1 to 3 (preferably 1) substituents selected from 2) Benzofuranylene [eg, benzofuran-2,5-diyl, benzofuran-2,6-diyl, especially

(In the formula, * represents a bonding position with X, and ** represents a bonding position with Y.)].

C is an optionally substituted carbocyclic group, an optionally substituted biaryl, an optionally substituted arylalkyl, an optionally substituted arylalkenyl, an optionally substituted alkyl, a substituted Or an optionally substituted cycloalkyl, an optionally substituted cycloalkyl, an optionally substituted cycloalkylalkyl, an optionally substituted heterocyclic group, or an optionally substituted heterocyclic alkenyl.

The “carbocyclic group” of the “optionally substituted carbocyclic group” represented by C is preferably a 6- to 10-membered carbocyclic group, more preferably phenyl, indenyl (eg, 2-indenyl). ), Indanyl (eg, 2-indanyl), naphthyl (eg, 1-naphthyl, 2-naphthyl), fluorenyl (eg, 2-fluorenyl, 9-fluorenyl), azulenyl (eg, azulen-1-yl).
The “carbocyclic group” may have one or more (preferably 1 to 3, more preferably 1 or 2) substituents at any substitutable position. Examples of such a substituent include the substituent group A described above. When the number of the substituents is 2 or more, these substituents may be the same or different.

The “optionally substituted carbocyclic group” is preferably
(1) (a) a halogen atom (eg, fluorine atom, chlorine atom, bromine atom),
(b) hydroxy,
(c) carboxy,
(d) cyano,
(e) Nitro,
(f) amino,
(g) alkyl (eg, methyl, isopropyl),
(h) alkoxy (eg, methoxy), and (i) aryl (eg, phenyl)
6- to 10-membered carbocyclic group optionally substituted with 1 to 3 substituents selected from [eg, phenyl, indanyl (eg, 2-indanyl), naphthyl (eg, 1-naphthyl, 2- Naphthyl), fluorenyl (eg, 2-fluorenyl, 9-fluorenyl), azulenyl (eg, azulen-1-yl)]
It is.

The biaryl of the “optionally substituted biaryl” represented by C is preferably C _12-18 biaryl, more preferably biphenylyl (eg, 4-biphenylyl, 2-biphenylyl, etc.) and the like.

The “optionally substituted biaryl” is preferably C _12-18 biaryl [eg, biphenylyl (eg, 4-biphenylyl, 2-biphenylyl)].

The “arylalkyl” of the “optionally substituted arylalkyl” represented by C is preferably C _6-10 aryl-C _1-6 alkyl, more preferably benzyl, naphthylethyl (eg, 2 -(2-naphthyl) ethyl).
The “arylalkyl” may have one or more (preferably 1 to 3, more preferably 1 or 2) substituents at any substitutable position. Examples of such a substituent include the substituent group A described above. When the number of the substituents is 2 or more, these substituents may be the same or different.

The “optionally substituted arylalkyl” is preferably C _6-10 aryl optionally substituted with 1 to 3 (preferably 1 or 2) halogen atoms (eg, chlorine atom). -C _1-6 alkyl [eg, benzyl, naphthylethyl (eg, 2- (2-naphthyl) ethyl)].

The “arylalkenyl” of the “optionally substituted arylalkenyl” represented by C is preferably C _6-10 aryl-C _2-6 alkenyl, more preferably naphthyl vinyl (eg, 2- ( 2-naphthyl) vinyl).
The “arylalkenyl” may have one or more (preferably 1 to 3, more preferably 1 or 2) substituents at any substitutable position. Examples of such a substituent include the substituent group A described above. When the number of the substituents is 2 or more, these substituents may be the same or different.

The “optionally substituted arylalkenyl” is preferably C _6-10 aryl-C _2-6 alkenyl, more preferably naphthyl vinyl (eg, 2- (2-naphthyl) vinyl). .

“Alkyl” of “optionally substituted alkyl” represented by C is preferably C _1-12 alkyl, more preferably methyl, ethyl, propyl, isopropyl, butyl, pentyl, hexyl, heptyl, Octyl and dodecyl.
The “alkyl” may have one or more (preferably 1 to 3, more preferably 1 or 2) substituents at any substitutable position. Examples of such a substituent include the following substituent group B. When the number of the substituents is 2 or more, these substituents may be the same or different.

[Substituent group B]
(1) a halogen atom,
(2) hydroxy,
(3) Carboxy,
(4) Cyano,
(5) Nitro,
(6) amino,
(7) alkoxy,
(8) aryloxy,
(9) Aromatic heterocyclic oxy,
(10) mono- or di-alkylamino,
(11) cycloalkyl,
(12) cycloalkoxy,
(13) (i) a halogen atom, and (ii) an aryl optionally substituted with 1 to 3 selected from alkyl optionally substituted with 1 to 7 halogen atoms,
(14) a non-aromatic heterocyclic group, and
(15) An aromatic heterocyclic group optionally substituted with 1 to 3 alkyls.

The “optionally substituted alkyl” is preferably
(a) hydroxy,
(b) alkoxy (eg butoxy),
(c) aryl optionally substituted by 1 to 3 halogen atoms (eg, chlorine atom) [eg, phenyl, naphthyl (eg, 2-naphthyl)], and
(d) Cycloalkyl (eg, cyclopropyl, cyclohexyl)
C _1-12 alkyl (eg, methyl, ethyl, propyl, isopropyl, butyl, pentyl, hexyl, heptyl, octyl) optionally substituted with 1 to 3 (preferably 1) substituents selected from , Dodecyl)
It is.

“Alkenyl” of “optionally substituted alkenyl” represented by C is preferably C _2-12 alkenyl, more preferably vinyl, butadienyl (eg, 1,3-butadienyl), heptatrienyl (eg, Hepta-1,3,5-trien-1-yl).
The “alkenyl” may have one or more (preferably 1 to 3, more preferably 1) substituents at any substitutable position. Examples of such a substituent include the substituent group B described above. When the number of the substituents is 2 or more, these substituents may be the same or different.

The “optionally substituted alkenyl” is preferably
(a) aryl [eg, naphthyl (eg, 2-naphthyl)], and
(b) Aromatic heterocyclic group [eg, furanyl (eg, 2-furanyl)]
C _2-12 alkenyl (eg, vinyl, 1,3-butadienyl, hepta-1,3,5-triene) optionally substituted with 1 to 3 (preferably 1) substituents selected from -1-Ile)
It is.

“Cycloalkyl” of “optionally substituted cycloalkyl” represented by C is preferably C _3-10 cycloalkyl, more preferably cyclopentyl or cyclohexyl.
The “cycloalkyl” may have one or more (preferably 1 to 3, more preferably 1) substituents at any substitutable position. Examples of such a substituent include the substituent group A described above. When the number of the substituents is 2 or more, these substituents may be the same or different.

The “optionally substituted cycloalkyl” is preferably C _3-10 cycloalkyl (eg, cyclopentyl, cyclohexyl).

“Cycloalkylalkyl” of “optionally substituted cycloalkylalkyl” represented by C is preferably C _3-6 cycloalkyl-C _1-6 alkyl, more preferably cyclohexylethyl (eg, 2-cyclohexylethyl), cyclopropylpropyl, cyclopropylbutyl, cyclopropylpentyl.
The “cycloalkylalkyl” may have one or more (preferably 1 to 3, more preferably 1) substituents at any substitutable position. Examples of such a substituent include the substituent group A described above. When the number of the substituents is 2 or more, these substituents may be the same or different.

The “optionally substituted cycloalkylalkyl” is preferably cycloalkylalkyl, more preferably C _3-6 cycloalkyl-C _1-6 alkyl [preferably cyclohexylethyl (eg, 2-ethyl Cyclohexylethyl), cyclopropylpropyl (eg, 3-cyclopropylpropyl), cyclopropylbutyl (eg, 4-cyclopropylbutyl), cyclopropylpentyl (eg, 5-cyclopropylpentyl)].

The “heterocyclic group” of the “optionally substituted heterocyclic group” represented by C is preferably thienyl (eg, 2-thienyl), isoxazolyl (eg, 4-isoxazolyl), quinolyl (eg, 6- Quinolyl), dibenzothiophenyl (eg, dibenzothiophen-2-yl), pyridyl, azocanyl (eg, 1-azocanyl).
The “heterocyclic group” may have one or more (preferably 1 to 3, more preferably 1 or 2) substituents at any substitutable position. Examples of such a substituent include the substituent group A described above. When the number of the substituents is 2 or more, these substituents may be the same or different.

The “optionally substituted heterocyclic group” is preferably
(a) a halogen atom (eg, a chlorine atom), and
(b) Alkyl (eg, methyl)
A heterocyclic group optionally substituted with 1 to 3 (preferably 1 or 2) substituents selected from [eg, thienyl (eg, 2-thienyl), isoxazolyl (eg, 4-isoxazolyl) , Quinolyl (eg, 6-quinolyl), dibenzothiophenyl (eg, dibenzothiophen-2-yl), azocanyl (eg, 1-azocanyl)]
It is.

The “aromatic heterocyclic alkenyl” of the “optionally substituted aromatic heterocyclic alkenyl” represented by C is preferably an aromatic heterocyclic-C _2-6 alkenyl, more preferably furylbutadiene. Enyl (eg, 4- (2-furyl) buta-1,3-dien-1-yl).
The “aromatic heterocyclic alkenyl” may have one or more (preferably 1 to 3, more preferably 1) substituents at any substitutable position. Examples of such a substituent include the substituent group A described above. When the number of the substituents is 2 or more, these substituents may be the same or different.

The “optionally substituted aromatic heterocyclic alkenyl” is preferably an aromatic heterocyclic alkenyl, more preferably an aromatic heterocyclic-C _2-6 alkenyl [preferably furylbutadienyl ( Example, 4- (2-furyl) buta-1,3-dien-1-yl)].

C is preferably an optionally substituted carbocyclic group, biaryl, optionally substituted arylalkyl, arylalkenyl, optionally substituted alkyl, optionally substituted alkenyl, cycloalkyl, cyclo An alkylalkyl, an optionally substituted aromatic heterocyclic group, an aromatic heterocyclic alkenyl or a 3 to 14-membered monocyclic non-aromatic heterocyclic group, specifically,
(1) (a) a halogen atom (eg, fluorine atom, chlorine atom, bromine atom),
(b) hydroxy,
(c) carboxy,
(d) cyano,
(e) Nitro,
(f) amino,
(g) alkyl (eg, methyl, isopropyl),
(h) alkoxy (eg, methoxy), and (i) aryl (eg, phenyl)
A carbocyclic group optionally substituted with 1 to 3 substituents selected from [eg, phenyl, indanyl (eg, 2-indanyl), naphthyl (eg, 1-naphthyl, 2-naphthyl), fluorenyl ( Examples, 2-fluorenyl, 9-fluorenyl), azulenyl (eg, azulen-1-yl)]],
(2) C _12-18 biaryl [eg, biphenylyl (eg, 4-biphenylyl, 2-biphenylyl)],
(3) arylalkyl optionally substituted with 1 to 3 halogen atoms (eg, chlorine atom) [eg, benzyl, naphthylethyl (2- (2-naphthyl) ethyl)],
(4) arylalkenyl [eg, naphthyl vinyl (eg, 2- (2-naphthyl) vinyl)],
(5) (a) hydroxy,
(b) alkoxy (eg butoxy),
(c) aryl optionally substituted with 1 to 3 halogen atoms (eg, chlorine atom) [eg, phenyl, naphthyl (eg, 2-naphthyl)], and (d) cycloalkyl (eg, cyclopropyl) Cyclohexyl)
C _1-12 alkyl (eg, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, dodecyl) optionally substituted by 1 to 3 (preferably 1) substituents selected from ),
(6) (a) aryl [eg, naphthyl (eg, 2-naphthyl)], and (b) aromatic heterocyclic group [eg, furanyl (eg, 2-furanyl)]
C _2-12 alkenyl (eg, vinyl, 1,3-butadienyl, hepta-1,3,5-triene) optionally substituted with 1 to 3 (preferably 1) substituents selected from -1-yl),
(7) C _3-10 cycloalkyl (eg, cyclopentyl, cyclohexyl),
(8) C _3-6 cycloalkyl-C _1-6 alkyl [eg, cyclohexylethyl (eg, 2-cyclohexylethyl), cyclopropylpropyl (eg, 3-cyclopropylpropyl), cyclopropylbutyl (eg, 4-cyclohexylethyl) Cyclopropylbutyl), cyclopropylpentyl (eg, 5-cyclopropylpentyl),
(9) (a) Halogen atom (eg, chlorine atom), and (b) Alkyl (eg, methyl)
An aromatic heterocyclic group optionally substituted with 1 to 3 (preferably 1 or 2) substituents selected from: [eg, thienyl (eg, 2-thienyl), isoxazolyl (eg, 4- Isoxazolyl), quinolyl (eg, 6-quinolyl), dibenzothiophenyl (eg, dibenzothiophen-2-yl)],
(10) Aromatic heterocyclic alkenyl (eg, furanyl-1,3-butadienyl), or (11) 3-14 membered monocyclic non-aromatic heterocyclic group [eg, azocanyl (eg, azocan-1-yl) ]]
It is.

In another embodiment, C is preferably an optionally substituted carbocyclic group, biaryl, an optionally substituted arylalkyl, an arylalkenyl, an optionally substituted alkyl, an optionally substituted alkenyl. , Cycloalkyl, cycloalkylalkyl, an optionally substituted aromatic heterocyclic group, an aromatic heterocyclic alkenyl or a 3 to 14-membered monocyclic non-aromatic heterocyclic group, specifically,
(1) (a) a halogen atom (eg, fluorine atom, chlorine atom, bromine atom),
(b) hydroxy,
(c) carboxy,
(d) cyano,
(e) Nitro,
(f) amino,
(g) alkyl (eg, methyl, isopropyl),
(h) alkoxy (eg, methoxy), and (i) aryl (eg, phenyl)
A carbocyclic group optionally substituted with 1 to 3 substituents selected from [eg, phenyl, indanyl (eg, 2-indanyl), naphthyl (eg, 1-naphthyl, 2-naphthyl), fluorenyl ( Examples, 2-fluorenyl, 9-fluorenyl), azulenyl (eg, azulen-1-yl)]],
(2) C _12-18 biaryl [eg, biphenylyl (eg, 4-biphenylyl, 2-biphenylyl)],
(3) arylalkyl optionally substituted with 1 to 3 halogen atoms (eg, chlorine atom) [eg, benzyl, naphthylethyl (2- (2-naphthyl) ethyl)],
(4) arylalkenyl [eg, naphthyl vinyl (eg, 2- (2-naphthyl) vinyl)],
(5) (a) hydroxy,
(b) alkoxy (eg butoxy),
(c) aryl optionally substituted with 1 to 3 halogen atoms (eg, chlorine atom) [eg, phenyl, naphthyl (eg, 2-naphthyl)],
(d) cycloalkyl (eg, cyclopropyl, cyclohexyl), and (e) an aromatic heterocyclic group optionally substituted with 1 to 3 alkyl groups (eg, methyl) [eg, oxadiazolyl (eg, [ 1,2,4] oxadiazol-5-yl)]
C _1-12 alkyl (eg, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, dodecyl) optionally substituted by 1 to 3 (preferably 1) substituents selected from ),
(6) (a) aryl [eg, naphthyl (eg, 2-naphthyl)], and (b) aromatic heterocyclic group [eg, furanyl (eg, 2-furanyl)]
C _2-12 alkenyl (eg, vinyl, 1,3-butadienyl, hepta-1,3,5-triene) optionally substituted with 1 to 3 (preferably 1) substituents selected from -1-yl),
(7) C _3-10 cycloalkyl (eg, cyclopentyl, cyclohexyl),
(8) C _3-6 cycloalkyl-C _1-6 alkyl [eg, cyclohexylethyl (eg, 2-cyclohexylethyl), cyclopropylpropyl (eg, 3-cyclopropylpropyl), cyclopropylbutyl (eg, 4-cyclohexylethyl) Cyclopropylbutyl), cyclopropylpentyl (eg, 5-cyclopropylpentyl),
(9) (a) Halogen atom (eg, chlorine atom), and (b) Alkyl (eg, methyl)
An aromatic heterocyclic group optionally substituted with 1 to 3 (preferably 1 or 2) substituents selected from: [eg, thienyl (eg, 2-thienyl), isoxazolyl (eg, 4- Isoxazolyl), quinolyl (eg, 6-quinolyl), dibenzothiophenyl (eg, dibenzothiophen-2-yl)],
(10) Aromatic heterocyclic alkenyl (eg, furanyl-1,3-butadienyl), or (11) 3-14 membered monocyclic non-aromatic heterocyclic group [eg, azocanyl (eg, azocan-1-yl) ]]
It is.

C is more preferably an optionally substituted aryl or an optionally substituted aromatic heterocyclic group, specifically,
(1) (a) a halogen atom (eg, fluorine atom, chlorine atom, bromine atom),
(b) alkyl (eg, methyl, isopropyl), and (c) alkoxy (eg, methoxy)
C _6-14 aryl optionally substituted with 1 to 3 substituents selected from [eg phenyl], or (2) 1 to 3 (preferably 1 or 2) halogen atoms ( Eg, a 5- or 6-membered aromatic heterocyclic group optionally substituted with a chlorine atom [eg, thienyl (eg, 2-thienyl)]
It is.
In another aspect, C is more preferably an optionally substituted aryl, an optionally substituted aromatic heterocyclic group, or an optionally substituted alkyl, specifically,
(1) (a) a halogen atom (eg, fluorine atom, chlorine atom, bromine atom),
(b) alkyl (eg, methyl, isopropyl), and (c) alkoxy (eg, methoxy)
C _6-14 aryl optionally substituted with 1 to 3 substituents selected from [eg phenyl],
(2) 5- or 6-membered aromatic heterocyclic group optionally substituted with 1 to 3 (preferably 1 or 2) halogen atoms (eg, chlorine atom) [eg, thienyl (eg, 2) -Thienyl)], or (3) alkyl (eg, hexyl)
It is.

C is more preferably an optionally substituted phenyl, biphenylyl, an optionally substituted naphthyl, an optionally substituted alkyl, a cycloalkylalkyl or an optionally substituted quinolyl, specifically Is
(1) (a) a halogen atom (eg, fluorine atom, chlorine atom, bromine atom),
(b) hydroxy,
(c) carboxy,
(d) cyano,
(e) Nitro,
(f) amino,
(g) alkyl (eg, methyl, isopropyl),
(h) alkoxy (eg, methoxy), and (i) phenyl optionally substituted with 1 to 3 substituents selected from aryl,
(2) biphenylyl (eg, 4-biphenylyl, 2-biphenylyl),
(3) naphthyl (eg, 1-naphthyl, 2-naphthyl) optionally substituted by 1 to 3 halogen atoms (eg, chlorine atom),
(4) (a) hydroxy,
(b) alkoxy (eg butoxy),
(c) aryl optionally substituted with 1 to 3 halogen atoms (eg, chlorine atom) [eg, phenyl, naphthyl (eg, 2-naphthyl)], and (d) cycloalkyl (eg, cyclopropyl) Cyclohexyl)
C _1-12 alkyl (eg, methyl, ethyl, propyl, butyl, pentyl, heptyl, octyl, dodecyl) optionally substituted with 1 to 3 (preferably 1) substituents selected from
(5) C _3-6 cycloalkyl-C _1-6 alkyl (eg, 2-cyclohexylethyl, 3-cyclopropylpropyl, 4-cyclopropylbutyl, 5-cyclopropylpentyl), or (6) quinolyl (eg, 6-quinolyl)
It is.

In another aspect, C is more preferably an optionally substituted aryl, an optionally substituted biaryl, an optionally substituted arylalkyl, an optionally substituted arylalkenyl, a substituted An optionally substituted alkyl, an optionally substituted alkenyl, an optionally substituted cycloalkyl, an optionally substituted cycloalkylalkyl, an optionally substituted aromatic heterocyclic group, or an optionally substituted A non-aromatic heterocyclic group, specifically,
(1) (a) a halogen atom (eg, chlorine atom, bromine atom),
(b) hydroxy,
(c) carboxy,
(d) cyano,
(e) Nitro,
(f) amino,
(g) aryl (eg, phenyl), and (h) alkyl (eg, methyl, isopropyl)
C _6-10 aryl optionally substituted with 1 to 3 substituents selected from [eg, phenyl, naphthyl (eg, 1-naphthyl, 2-naphthyl), azulenyl (eg, azulen-1-yl) )],
(2) Biaryl [eg, biphenylyl (eg, 4-biphenylyl, 2-biphenylyl)],
(3) C _6-10 aryl-C _1-6 alkyl optionally substituted by 1 to 3 (preferably 1 or 2) halogen atoms (eg, chlorine atom) [eg, benzyl, naphthylethyl (Eg, 2- (2-naphthyl) ethyl)],
(4) arylalkenyl [eg, naphthyl vinyl (eg, 2- (2-naphthyl) vinyl)],
(5) (a) hydroxy,
(b) alkoxy (eg butoxy),
(c) aryl optionally substituted with 1 to 3 halogen atoms (eg, chlorine atom) [eg, phenyl, naphthyl (eg, 2-naphthyl)], and (d) cycloalkyl (eg, cyclopropyl, Cyclohexyl)
C _1-12 alkyl (eg, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, dodecyl) optionally substituted by 1 to 3 (preferably 1) substituents selected from ),
(6) (a) aryl [eg, naphthyl (eg, 2-naphthyl)], and (b) aromatic heterocyclic group [eg, furanyl (eg, 2-furanyl)]
C _2-12 alkenyl optionally substituted with 1 to 3 (preferably 1) substituents selected from [eg, vinyl, 1,3-butadienyl, heptatrienyl (eg, hepta-1,3) , 5-trien-1-yl)],
(7) C _3-6 cycloalkyl (eg, cyclopentyl, cyclohexyl),
(8) C _3-6 cycloalkyl-C _1-6 alkyl (eg, 2-cyclohexylethyl, 3-cyclopropylpropyl, 4-cyclopropylbutyl, 5-cyclopropylpentyl),
(9) A 5- to 14-membered aromatic heterocyclic group optionally substituted by 1 to 3 (preferably 1 or 2) alkyl (eg, methyl) [eg, isoxazolyl (eg, 4-isoxazolyl) ), Quinolyl (eg, 6-quinolyl), dibenzothiophenyl (eg, dibenzothiophen-2-yl)], or (10) a 5- to 14-membered non-aromatic heterocyclic group [eg, azocanyl (eg, azocan- 1-yl)]
It is.
In another aspect, C is more preferably an optionally substituted aryl, an optionally substituted biaryl, an optionally substituted arylalkyl, an optionally substituted arylalkenyl, a substituted An optionally substituted alkyl, an optionally substituted alkenyl, an optionally substituted cycloalkyl, an optionally substituted cycloalkylalkyl, an optionally substituted aromatic heterocyclic group, or an optionally substituted A non-aromatic heterocyclic group, specifically,
(1) (a) a halogen atom (eg, chlorine atom, bromine atom),
(b) hydroxy,
(c) carboxy,
(d) cyano,
(e) Nitro,
(f) amino,
(g) aryl (eg, phenyl), and (h) alkyl (eg, methyl, isopropyl)
C _6-10 aryl optionally substituted with 1 to 3 substituents selected from [eg, phenyl, naphthyl (eg, 1-naphthyl, 2-naphthyl), azulenyl (eg, azulen-1-yl) )],
(2) Biaryl [eg, biphenylyl (eg, 4-biphenylyl, 2-biphenylyl)],
(3) C _6-10 aryl-C _1-6 alkyl optionally substituted by 1 to 3 (preferably 1 or 2) halogen atoms (eg, chlorine atom) [eg, benzyl, naphthylethyl (Eg, 2- (2-naphthyl) ethyl)],
(4) arylalkenyl [eg, naphthyl vinyl (eg, 2- (2-naphthyl) vinyl)],
(5) (a) hydroxy,
(b) alkoxy (eg butoxy),
(c) aryl optionally substituted with 1 to 3 halogen atoms (eg, chlorine atom) [eg, phenyl, naphthyl (eg, 2-naphthyl)],
(d) cycloalkyl (eg, cyclopropyl, cyclohexyl), and (e) an aromatic heterocyclic group optionally substituted with 1 to 3 alkyl groups (eg, methyl) [eg, oxadiazolyl (eg, [ 1,2,4] oxadiazol-5-yl)]
C _1-12 alkyl (eg, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, dodecyl) optionally substituted by 1 to 3 (preferably 1) substituents selected from ),
(6) (a) aryl [eg, naphthyl (eg, 2-naphthyl)], and (b) aromatic heterocyclic group [eg, furanyl (eg, 2-furanyl)]
C _2-12 alkenyl optionally substituted with 1 to 3 (preferably 1) substituents selected from [eg, vinyl, 1,3-butadienyl, heptatrienyl (eg, hepta-1,3) , 5-trien-1-yl)],
(7) C _3-6 cycloalkyl (eg, cyclopentyl, cyclohexyl),
(8) C _3-6 cycloalkyl-C _1-6 alkyl (eg, 2-cyclohexylethyl, 3-cyclopropylpropyl, 4-cyclopropylbutyl, 5-cyclopropylpentyl),
(9) A 5- to 14-membered aromatic heterocyclic group optionally substituted by 1 to 3 (preferably 1 or 2) alkyl (eg, methyl) [eg, isoxazolyl (eg, 4-isoxazolyl) ), Quinolyl (eg, 6-quinolyl), dibenzothiophenyl (eg, dibenzothiophen-2-yl)], or (10) a 5- to 14-membered non-aromatic heterocyclic group [eg, azocanyl (eg, azocan- 1-yl)]
It is.

C is even more preferably an optionally substituted phenyl, an optionally substituted naphthyl, an optionally substituted alkyl, an optionally substituted cycloalkylalkyl, or an optionally substituted quinolyl. Specifically,
(1) (a) a halogen atom (eg, chlorine atom, bromine atom),
(b) hydroxy,
(c) carboxy,
(d) cyano,
(e) Nitro,
(f) amino, and (g) aryl (eg, phenyl)
Phenyl optionally substituted with 1 to 3 substituents selected from
(2) naphthyl (eg, 1-naphthyl, 2-naphthyl) optionally substituted with 1 to 3 halogen atoms (eg, chlorine atom),
(3) (a) hydroxy,
(b) alkoxy (eg butoxy),
(c) aryl (eg, phenyl, naphthyl) optionally substituted with 1 to 3 halogen atoms (eg, chlorine atom), and (d) cycloalkyl (eg, cyclohexyl)
C _1-12 alkyl (eg, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, dodecyl) optionally substituted by 1 to 3 (preferably 1) substituents selected from ),
(4) C _3-6 cycloalkyl-C _1-6 alkyl (eg, 2-cyclohexylethyl, 3-cyclopropylpropyl, 4-cyclopropylbutyl, 5-cyclopropylpentyl), or (5) quinolyl (eg, 6-quinolyl)
It is.
In another aspect, C is even more preferably an optionally substituted phenyl, an optionally substituted naphthyl, an optionally substituted alkyl, an optionally substituted cycloalkylalkyl, or a substituted Quinolyl, which may be
(1) (a) a halogen atom (eg, chlorine atom, bromine atom),
(b) hydroxy,
(c) carboxy,
(d) cyano,
(e) Nitro,
(f) amino, and (g) aryl (eg, phenyl)
Phenyl optionally substituted with 1 to 3 substituents selected from
(2) naphthyl (eg, 1-naphthyl, 2-naphthyl) optionally substituted with 1 to 3 halogen atoms (eg, chlorine atom),
(3) (a) hydroxy,
(b) alkoxy (eg butoxy),
(c) aryl (eg, phenyl, naphthyl) optionally substituted by 1 to 3 halogen atoms (eg, chlorine atom),
(d) cycloalkyl (eg, cyclohexyl), and (e) an aromatic heterocyclic group optionally substituted with 1 to 3 alkyl groups (eg, methyl) [eg, oxadiazolyl (eg, [1,2 , 4] oxadiazol-5-yl)]
C _1-12 alkyl (eg, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, dodecyl) optionally substituted by 1 to 3 (preferably 1) substituents selected from ),
(4) C _3-6 cycloalkyl-C _1-6 alkyl (eg, 2-cyclohexylethyl, 3-cyclopropylpropyl, 4-cyclopropylbutyl, 5-cyclopropylpentyl), or (5) quinolyl (eg, 6-quinolyl)
It is.

X is
Optionally substituted alkylene,
Optionally substituted alkenylene,
Optionally substituted alkynylene,
Optionally substituted * — (CH ₂ ) _m —O— (CH ₂ ) _n — **,
Optionally substituted * — (CH ₂ ) _m —S (O) _p — (CH ₂ ) _n — **,
Optionally substituted * — (CH ₂ ) _m —N (R ¹ ) — (CH ₂ ) _n — **,
Optionally substituted * — (CH ₂ ) _m —CO— (CH ₂ ) _n — **,
Optionally substituted * — (CH ₂ ) _q —CO—N (R ¹ ) — (CH ₂ ) _r — **,
Optionally substituted * — (CH ₂ ) _q —N (R ¹ ) —CO— (CH ₂ ) _r — **,
Optionally substituted * — (CH ₂ ) _q —SO ₂ —N (R ¹ ) — (CH ₂ ) _r — **,
Optionally substituted * — (CH ₂ ) _q —N (R ¹ ) —SO ₂ — (CH ₂ ) _r — **,
* -C (R ¹ ) = N—O — **, or * —O—N = C (R ¹ ) — **
(Wherein m, n, q and r each independently represent 0 or an integer of 1 to 4, p represents 0, 1 or 2, R ¹ represents a hydrogen atom or lower alkyl, * Indicates a bonding position with A, and ** indicates a bonding position with B).

“Alkylene”, “alkenylene”, “alkynylene”, “* — (CH ₂ ) _m —O— (CH ₂ ) _n — **”, “* — (CH ₂ ) _m —S (O)” represented by X _p- (CH ₂ ) _n -** "," *-(CH ₂ ) _m -N (R ¹ )-(CH ₂ ) _n -** "," *-(CH ₂ ) _m -CO- (CH ₂ ) _n -** "," *-(CH ₂ ) _q -CO-N (R ¹ )-(CH ₂ ) _r -** "," *-(CH ₂ ) _q -N (R ¹ )- CO— (CH ₂ ) _r — ** ”,“ * — (CH ₂ ) _q —SO ₂ —N (R ¹ ) — (CH ₂ ) _r — ** ”, and“ * — (CH ₂ ) _q — N (R ¹ ) —SO ₂ — (CH ₂ ) _r — ** ”is one or more (preferably 1 to 3, more preferably 1 or 2) substituents at any substitutable position. Have It may be. Examples of such a substituent include the substituent group A described above. When the number of the substituents is 2 or more, these substituents may be the same or different.

The “alkylene” is preferably C _1-6 alkylene (eg, methylene, ethylene, trimethylene).

The “alkenylene” is preferably C _2-6 alkenylene, more preferably vinylene.

The “alkynylene” is preferably C _2-6 alkynylene, more preferably ethynylene.

m is preferably 0, 1 or 2.
n is preferably 0 or 1.
q is preferably 0 or 1.
r is preferably 0 or 1.
p is preferably 0, 1 or 2.

The “* — (CH ₂ ) _m —O— (CH ₂ ) _n — **” is preferably —O—, * —CH ₂ —O — **, —CH ₂ —O—CH ₂ —, Or * — (CH ₂ ) ₂ —O — **.

In another embodiment, the “* — (CH ₂ ) _m —O— (CH ₂ ) _n — **” is preferably —O—, * —CH ₂ —O — **, —CH ₂ —O. —CH ₂ —, * — (CH ₂ ) ₂ —O — **, or * —O—CH ₂ — **.

The “*-(CH ₂ ) _m —S (O) _p — (CH ₂ ) _n — **” is preferably —S—, —CH ₂ —S—CH ₂ —, —CH ₂ —SO—. CH ₂ —, or —CH ₂ —SO ₂ —CH ₂ —.

The “*-(CH ₂ ) _m —N (R ¹ ) — (CH ₂ ) _n — **” is preferably —NH—, —CH ₂ —NH—CH ₂ — or —CH ₂ —N ( CH ₃ ) —CH ₂ —.

The “*-(CH ₂ ) _m —CO— (CH ₂ ) _n — **” is preferably —CO—.

The “* — (CH ₂ ) _q —CO—N (R ¹ ) — (CH ₂ ) _r — **” is preferably * —CH ₂ —CO—NH—CH ₂ — **.

The “* — (CH ₂ ) _q —N (R ¹ ) —CO— (CH ₂ ) _r — **” is preferably * —CH ₂ —NH—CO—CH ₂ — **.

The “* — (CH ₂ ) _q —SO ₂ —N (R ¹ ) — (CH ₂ ) _r — **” is preferably * —CH ₂ —SO ₂ —NH—CH ₂ — **. .

The “*-(CH ₂ ) _q —N (R ¹ ) —SO ₂ — (CH ₂ ) _r — **” is preferably * —CH ₂ —NH—SO ₂ —CH ₂ — **. .

“* —C (R ¹ ) ═N—O — **” represented by X is preferably * —CH═N—O — ** or * —C (CH ₃ ) = N—O — **. It is. “Lower alkyl” represented by R ¹ is preferably methyl.

X is preferably an optionally substituted alkylene, an optionally substituted alkenylene, an optionally substituted alkynylene, an optionally substituted * — (CH ₂ ) _m —O— (CH ₂ ). _n -**, optionally substituted * — (CH ₂ ) _m —S (O) _p — (CH ₂ ) _n — **, optionally substituted * — (CH ₂ ) _m —CO— (CH ₂ ) _n — **, optionally substituted * — (CH ₂ ) _q —CO—N (R ¹ ) — (CH ₂ ) _r — **, or * —C (R ¹ ) = N -O-** (wherein m, n, q and r each independently represents 0 or an integer of 1 to 4, p represents 0, 1 or 2; R ¹ represents a hydrogen atom or lower An alkyl, * represents a bonding position with A, ** represents a bonding position with B, and specifically,
(1) alkylene (eg, methylene, ethylene, trimethylene) optionally substituted with 1 to 3 (preferably 1) arylalkyloxy (eg, benzyloxy),
(2) Alkenylene (eg, vinylene),
(3) alkynylene (eg, acetylene-1,2-diyl),
(4) (a) aryl (eg, phenyl), and (b) aromatic heterocyclic group [eg, thiazolyl (eg, 2-thiazolyl)]
* — (CH ₂ ) _m —O— (CH ₂ ) _n — ** (eg, —O) optionally substituted with 1 to 3 (preferably 1 or 2) substituents selected from -, * -CH ₂ -O-**, -CH ₂ -O-CH _2- , *-(CH ₂ ) ₂ -O-**),
(5) * — (CH ₂ ) _m —S (O) _p — (CH ₂ ) _n — ** (eg, —S—, —CH ₂ —S—CH ₂ —, —CH ₂ —SO—CH ₂ _{_{_{-, - CH 2 -SO 2 -CH}}} 2 -),
(6) **-(CH ₂ ) _m —CO— (CH ₂ ) _n — ** (eg, —CO—),
(7) * — (CH ₂ ) _q —CO—N (R ¹ ) — (CH ₂ ) _r — ** (eg, * —CH ₂ —CO—NH—CH ₂ — **), or (8) * —C (R ¹ ) ═N—O — ** (R ¹ is a hydrogen atom or lower alkyl (eg, methyl).)
(In the above (1) to (8), m, n, q and r each independently represent 0 or an integer of 1 to 4, p represents 0, 1 or 2, and * represents the bonding position with A. ** indicates the position of binding to B.)
It is.
In another embodiment, X is preferably an optionally substituted alkylene, an optionally substituted alkenylene, an optionally substituted alkynylene, an optionally substituted * — (CH ₂ ) _m —O. — (CH ₂ ) _n — **, optionally substituted * — (CH ₂ ) _m —S (O) _p — (CH ₂ ) _n — **, optionally substituted * — (CH ₂ _{^{) m -N (R 1) -}} (CH 2) n - **, optionally substituted _{_{* - (CH 2) m -CO-}} (CH 2) n - **, optionally substituted * — (CH ₂ ) _q —CO—N (R ¹ ) — (CH ₂ ) _r — ** or * —C (R ¹ ) = NO — ** (where m, n, q and r Each independently represents 0 or an integer of 1 to 4, p represents 0, 1 or 2, R ¹ represents a hydrogen atom or Represents a lower alkyl, * represents a bonding position with A, ** represents a bonding position with B, and specifically,
(1) alkylene (eg, methylene, ethylene, trimethylene) optionally substituted with 1 to 3 (preferably 1) arylalkyloxy (eg, benzyloxy),
(2) Alkenylene (eg, vinylene),
(3) alkynylene (eg, acetylene-1,2-diyl),
(4) (a) aryl (eg, phenyl), and (b) 5- to 14-membered aromatic heterocyclic group [eg, thiazolyl (eg, 2-thiazolyl)]
* — (CH ₂ ) _m —O— (CH ₂ ) _n — ** which may be substituted with 1 to 3 (preferably 1 or 2) substituents selected from O—, * —CH ₂ —O — **, —CH ₂ —O—CH ₂ —, * — (CH ₂ ) ₂ —O — **, * —O—CH ₂ — **),
(5) * — (CH ₂ ) _m —S (O) _p — (CH ₂ ) _n — ** (eg, —S—, —CH ₂ —S—CH ₂ —, —CH ₂ —SO—CH ₂ _{_{_{-, - CH 2 -SO 2 -CH}}} 2 -),
(6) **-(CH ₂ ) _m —CO— (CH ₂ ) _n — ** (eg, —CO—),
(7) * — (CH ₂ ) _q —CO—N (R ¹ ) — (CH ₂ ) _r — ** (eg, * —CH ₂ —CO—NH—CH ₂ — **),
(8) *-C (R ¹ ) = NO — ** (where R ¹ is a hydrogen atom or lower alkyl (eg, methyl)), or (9) * — (CH ₂ ) _m —N (R ¹ ) — (CH ₂ ) _n — ** (eg, —CH ₂ —N (CH ₃ ) —CH ₂ —)
(In the above (1) to (9), m, n, q and r each independently represent 0 or an integer of 1 to 4, p represents 0, 1 or 2, and * represents A and (The bond position is indicated, and ** indicates the bond position with B.)
It is.

X is more preferably an optionally substituted * — (CH ₂ ) _m —O— (CH ₂ ) _n — **, or an optionally substituted * — (CH ₂ ) _m —S (O _P- (CH ₂ ) _n -** (wherein, m and n each independently represents an integer of 1 to 4, p represents 0 or 2, * represents a bonding position with A) , ** represents a bonding position with B.) (preferably —CH ₂ —O—CH ₂ — or —CH ₂ —S—CH ₂ —), specifically,
(1) (a) aryl (eg, phenyl), and (b) aromatic heterocyclic group [eg, thiazolyl (eg, 2-thiazolyl)]
* — (CH ₂ ) _m —O— (CH ₂ ) _n — ** (eg, —CH ₂ —) which may be substituted with 1 to 3 (preferably 1) substituents selected from O—CH ₂ —), or (2) * — (CH ₂ ) _m —S (O) _p — (CH ₂ ) _n — ** (eg, —CH ₂ —S—CH ₂ — or —CH ₂ — SO ₂ —CH ₂ —)
It is.
In another embodiment, more preferably, * — (CH ₂ ) _m —O— (CH ₂ ) _n — **, which may be substituted, * — (CH ₂ ) _m —S (which may be substituted) O) _p- (CH ₂ ) _n -**, or optionally substituted *-(CH ₂ ) _m -N (R ¹ )-(CH ₂ ) _n -** (where m and n are Each independently represents an integer of 1 to 4, p represents 0 or 2, R ¹ represents a hydrogen atom or lower alkyl, * represents a bonding position with A, and ** represents a bond with B. (Preferably —CH ₂ —O—CH ₂ —, —CH ₂ —S—CH ₂ — or —CH ₂ —N (CH ₃ ) —CH ₂ —), specifically Is
(1) (a) aryl (eg, phenyl), and (b) aromatic heterocyclic group [eg, thiazolyl (eg, 2-thiazolyl)]
* — (CH ₂ ) _m —O— (CH ₂ ) _n — ** (eg, —CH ₂ —) which may be substituted with 1 to 3 (preferably 1) substituents selected from O—CH ₂ —),
(2) * — (CH ₂ ) _m —S (O) _p — (CH ₂ ) _n — ** (eg, —CH ₂ —S—CH ₂ — or —CH ₂ —SO ₂ —CH ₂ —), Or (3) * — (CH ₂ ) _m —N (R ¹ ) — (CH ₂ ) _n — ** (eg, —CH ₂ —N (CH ₃ ) —CH ₂ —)
It is.

X is more preferably an optionally substituted * — (CH ₂ ) _m —O— (CH ₂ ) _n — **, an optionally substituted * — (CH ₂ ) _m —S (O) _p- (CH ₂ ) _n -**, or * -C (R ¹ ) = NO-** (wherein m represents 0, 1 or 2, n represents 0, 1 or 2; p represents 0 or 2, R ¹ represents a hydrogen atom or lower alkyl, * represents a bonding position with A, and ** represents a bonding position with B.), more preferably
(1) optionally substituted * — (CH ₂ ) _m —O— (CH ₂ ) _n — ** [preferably 1 to 3 (preferably 1) aryl (preferably phenyl) —CH ₂ —O—CH ₂ — or —O—] optionally substituted by
(2) * — (CH ₂ ) _m —S (O) _p — (CH ₂ ) _n — ** (preferably —S—, —CH ₂ —S—CH ₂ —, —CH ₂ —SO ₂ — CH _2- ), or (3) * -C (R ¹ ) = NO-** (preferably * -CH = NO-**, * -C (CH ₃ ) = NO- **, * —C (CH ₂ CH ₂ CH ₂ CH ₃ ) = N—O — **).

In another embodiment, X is more preferably an optionally substituted * — (CH ₂ ) _m —O— (CH ₂ ) _n — **, an optionally substituted * — (CH ₂ ) _m —S (O) _p — (CH ₂ ) _n — **, or * —C (R ¹ ) = N—O — ** (wherein m represents 0, 1 or 2, and n represents 0, 1 Or 2; p represents 0 or 2; R ¹ represents a hydrogen atom or lower alkyl; * represents a bonding position with A; ** represents a bonding position with B); Preferably,
(1) (a) aryl (eg, phenyl), and (b) aromatic heterocyclic group [eg, thiazolyl (eg, 2-thiazolyl)]
* — (CH ₂ ) _m —O— (CH ₂ ) _n — ** (preferably — may be substituted with 1 to 3 (preferably 1 or 2) substituents selected from CH ₂ —O—CH ₂ — or —O—),
(2) * — (CH ₂ ) _m —S (O) _p — (CH ₂ ) _n — ** (preferably —S—, —CH ₂ —S—CH ₂ —, —CH ₂ —SO ₂ — CH _2- ), or (3) * -C (R ¹ ) = NO-** (preferably * -CH = NO-**, * -C (CH ₃ ) = NO- **, * —C (CH ₂ CH ₂ CH ₂ CH ₃ ) = N—O — **).

X is even more preferably * — (CH ₂ ) _m —O— (CH ₂ ) _n — ** or optionally substituted * — (CH ₂ ) _m —S (O ) _P- (CH ₂ ) _n -** (wherein, m and n each independently represents 0 or an integer of 1 to 4, p represents 0 or 2, and * represents a bonding position with A) , ** represents a bonding position with B.) (Preferably —O—, —CH ₂ —O—CH ₂ — or —CH ₂ —S—CH ₂ —), specifically,
(1) (a) aryl (eg, phenyl), and (b) aromatic heterocyclic group [eg, thiazolyl, (eg, 2-thiazolyl)]
* — (CH ₂ ) _m —O— (CH ₂ ) _n — ** (eg, —CH ₂ —) which may be substituted with 1 to 3 (preferably 1) substituents selected from O—CH ₂ —, * — (CH ₂ ) ₂ —O — **, —O—), or (2) * — (CH ₂ ) _m —S (O) _p — (CH ₂ ) _n — ** _{_{(eg, -S -, - CH 2 -S}} -CH 2 -, - CH 2 -SO 2 -CH 2 -)
It is.
In another embodiment, X is even more preferably * — (CH ₂ ) _m —O— (CH ₂ ) _n — **, optionally substituted * — (CH ₂ ). _m —S (O) _p — (CH ₂ ) _n — **, or optionally substituted * — (CH ₂ ) _m —N (R ¹ ) — (CH ₂ ) _n — ** (wherein m and n each independently represents 0 or an integer of 1 to 4, p represents 0 or 2, R ¹ represents a hydrogen atom or lower alkyl, * represents a bonding position with A, ** represents The bonding position to B is shown.) (Preferably —O—, —CH ₂ —O—CH ₂ —, —CH ₂ —S—CH ₂ — or —CH ₂ —N (CH ₃ ) —CH ₂ — ), Specifically,
(1) (a) aryl (eg, phenyl), and (b) aromatic heterocyclic group [eg, thiazolyl (eg, 2-thiazolyl)]
* — (CH ₂ ) _m —O— (CH ₂ ) _n — ** (eg, —CH ₂ —) which may be substituted with 1 to 3 (preferably 1) substituents selected from O—CH ₂ —, * — (CH ₂ ) ₂ —O — **, —O—),
(2) * — (CH ₂ ) _m —S (O) _p — (CH ₂ ) _n — ** (eg, —S—, —CH ₂ —S—CH ₂ —, —CH ₂ —SO ₂ —CH _2- ), or (3) *-(CH ₂ ) _m -N (R ¹ )-(CH ₂ ) _n -** (eg, -CH ₂ -N (CH ₃ ) -CH _2- )
It is.

In another embodiment, X is more preferably * —C (R ¹ ) ═N—O — ** (wherein R ¹ represents a hydrogen atom or lower alkyl, and * represents a bonding position with A). , ** represents a bonding position with B) (for example, * -CH = NO-** or * -C (CH ₃ ) = NO-**).

In another embodiment, X is more preferably * — (CH ₂ ) _m —O— (CH ₂ ) _n — **, or * — (CH ₂ ) _m —S (O) _p — (CH ₂ ). _n -** (wherein m and n each independently represents an integer of 1 to 4, p represents 0 or 2, * represents a bonding position with A, and ** represents a bonding position with B. And specifically,
(1) * — (CH ₂ ) _m —O— (CH ₂ ) _n — ** [preferably substituted with 1 to 3 (preferably 1) aryl (preferably phenyl) Good —CH ₂ —O—CH ₂ —], or (2) * — (CH ₂ ) _m —S (O) _p — (CH ₂ ) _n — ** (preferably —S—, —CH ₂ — _{_{_{S-CH 2 -, - CH}}} 2 -SO 2 -CH 2 -)
It is.

X is even more preferably —CH ₂ —O—CH ₂ — or —CH ₂ —S—CH ₂ —.

Z is * -CONHSO ₂ -**, * -SO ₂ NHCO-**, * -N (R ² ) CONHSO ₂ -**, * -SO ₂ NHCON (R ² )-**, * -CONHSO ₂ N (R ² )-**, * -N (R ² ) SO ₂ NHCO-**, * -COCONHSO ₂ -**, * -SO ₂ NHCOCO-**, * -N (R ² ) COCONHSO _2- ** or * -SO ₂ NHCOCON (R ² )-** (wherein R ² represents a hydrogen atom or lower alkyl, * represents a bonding position with B, ** represents a bonding position with C) Is shown.)

The “lower alkyl” represented by R ² is preferably C _1-6 alkyl.

R ² is preferably a hydrogen atom or C _1-6 alkyl (eg, butyl), more preferably a hydrogen atom.

Z is preferably * -CONHSO ₂ -**, * -SO ₂ NHCO-**, * -N (R ² ) CONHSO ₂ -**, * -CONHSO ₂ N (R ² )-**, or * —CONCONHSO ₂ — ** (wherein R ² represents a hydrogen atom or lower alkyl, * represents a bonding position with B, and ** represents a bonding position with C), specifically Is
(1) * -CONHSO ₂ -**,
(2) * -SO ₂ NHCO-**,
(3) * -NHCONHSO ₂ -**,
(4) *-CONHSO ₂ N (R ² )-** (where R ² is a hydrogen atom or lower alkyl (eg, butyl)), or (5) *-CONCONHSO ₂ -**
(In the above (1) to (5), * indicates the bonding position with B, and ** indicates the bonding position with C.)
It is.

In another aspect, Z is preferably
* -CONHSO ₂ -**,
* -SO ₂ NHCO-**,
* -NHCONHSO ₂ -**,
* -SO ₂ NHCONH-**,
* -CONHSO ₂ NH-**,
* -NHSO ₂ NHCO-**,
* -CONCONSO ₂ -**,
* -SO ₂ NHCOCO-**,
* -NHCOCONHSO ₂ -** or * -SO ₂ NHCOCONH-**.

Z is more preferably * -CONHSO ₂ -**, * -SO ₂ NHCO-**, * -N (R ² ) CONHSO ₂ -**, * -CONHSO ₂ N (R ² )-**, * -CONCONHSO ₂ -**, or * -N (R ² ) COCONHSO ₂ -** (wherein R ² represents a hydrogen atom or lower alkyl, * represents a bonding position with B, and ** Represents a bonding position with C), specifically,
(1) * -CONHSO ₂ -**,
(2) * -SO ₂ NHCO-**,
(3) * -NHCONHSO ₂ -**,
(4) * -CONHSO ₂ N (R ² )-** (R ² is a hydrogen atom or lower alkyl (eg, butyl)),
(5) * -CONCONHSO ₂ -** or (6) *-NHCONCONHSO ₂ -**
(In the above (1) to (6), * indicates the bonding position with B, and ** indicates the bonding position with C).

Z is more preferably * -CONHSO ₂ -**, * -NHCONHSO ₂ -**, * -CONHSO ₂ NH-**, * -CONCONHSO ₂ -**, or * -NHCONCONHSO ₂ -**. .

In another embodiment, Z is more preferably * -CONHSO ₂ -**, * -SO ₂ NHCO-**, * -N (R ² ) CONHSO ₂ -**, * -CONHSO ₂ N (R ² )-**, * -CONCONSO ₂ -**, or * -N (R ² ) CONONSO ₂ -** (wherein R ² represents a hydrogen atom or lower alkyl, and * represents the position of bonding to B) ** indicates the bonding position with C.), specifically, * -CONHSO ₂ -**, * -SO ₂ NHCO-**, * -CONHSO ₂ N (R ² )-* *, * -NHCONHSO ₂ -**, * -CONCONHSO ₂ -**, or * -NHCOCONHSO ₂ -** (R ² is a hydrogen atom or butyl).
Furthermore, in another aspect, Z is more preferably * -CONHSO ₂ -**, * -N (R ² ) CONHSO ₂ -**, * -CONHSO ₂ N (R ² )-**, *- COCONHSO ₂ -** or * -N (R ² ) COCONHSO ₂ -** (wherein R ² represents a hydrogen atom or an optionally substituted lower alkyl, * represents a bonding position with Y, * * Indicates a bonding position with C.), specifically, * -CONHSO ₂ -**, * -NHCONHSO ₂ -**, * -CONHSO ₂ NH-**, * -CONHSO ₂ N ( Bu)-**, * -SO ₂ NHCO-**, * -COCONHSO ₂ -**, or * -NHCOCONHSO ₂ -** (wherein, * indicates the bonding position with B, ** is C and Indicates the bonding position of The

Z is even more preferably * -CONHSO ₂ -** (wherein * represents a bonding position with B and ** represents a bonding position with C).

The compound represented by formula (I) is preferably
A is an optionally substituted carbocyclic group, an optionally substituted biaryl, or an optionally substituted heterocyclic group;
B is a divalent carbocyclic group that may be substituted, a biarylene that may be substituted, or a divalent heterocyclic group that may be substituted;
C is an optionally substituted carbocyclic group, an optionally substituted biaryl, an optionally substituted arylalkyl, an optionally substituted arylalkenyl, an optionally substituted alkyl, a substituted An optionally substituted alkenyl, an optionally substituted cycloalkyl, an optionally substituted cycloalkylalkyl, an optionally substituted heterocyclic group, or an optionally substituted heterocyclic alkenyl,
X is an optionally substituted alkylene, an optionally substituted alkenylene, an optionally substituted alkynylene, an optionally substituted * — (CH ₂ ) _m —O— (CH ₂ ) _n — * *, Optionally substituted * — (CH ₂ ) _m —S (O) _p — (CH ₂ ) _n — **, optionally substituted * — (CH ₂ ) _m —CO— (CH ₂ ) _n - **, optionally substituted _{_{^{* - (CH 2) q -CO}}} -n (R 1) - (CH 2) r - **, or ^{* -C (R 1) = n} -O- ** (wherein m, n, q and r each independently represents 0 or an integer of 1 to 4, p represents 0, 1 or 2; R ¹ represents a hydrogen atom or lower alkyl; * Indicates the position of bonding with A, and ** indicates the position of bonding with B.)
Z is * -CONHSO ₂ -**, * -SO ₂ NHCO-**, * -N (R ² ) CONHSO ₂ -**, * -CONHSO ₂ N (R ² )-**, * -CONCONHSO ₂ -**, or * -N (R ² ) CONONSO ₂ -** (wherein R ² represents a hydrogen atom or lower alkyl, * represents a bonding position with B, ** represents C and In particular, the bonding position of
A is
(1) (a) a halogen atom (eg, chlorine atom),
(b) Nitro,
(c) alkyl (eg, methyl, isopropyl, tert-butyl, hexyl) optionally substituted with 1 to 5 halogen atoms (eg, fluorine atom),
(d) alkenyl (eg, 2-methyl-1-propenyl, 4-methyl-1-pentenyl, 5-methyl-1-hexenyl),
(e) arylalkenyl [eg, phenyl vinyl (eg, 2-phenyl vinyl)],
(f) alkynyl (eg, ethynyl),
(g) arylalkynyl (eg, phenylethynyl),
(h) heterocyclic alkynyl [eg, thiazolylethynyl (eg, thiazol-5-ylethynyl)],
(i) alkoxy (eg, isopropoxy),
(j) mono- or di-alkylamino (eg ethylamino, dimethylamino, diethylamino),
(k) cycloalkyl (eg, cyclobutyl),
(l) (i) a halogen atom (eg, fluorine atom, chlorine atom), and (ii) an alkyl optionally substituted with 1 to 7 halogen atoms (eg, fluorine atom) (eg, methyl, isopropyl)
Aryl (eg, phenyl) optionally substituted with 1 to 3 (preferably 1 or 2) substituents selected from
(m) non-aromatic heterocyclic group [eg, pyrrolidinyl (eg, 1-pyrrolidinyl)], and (n) aromatic heterocyclic group [eg, furyl (eg, 2-furyl), thienyl (eg, 2-thienyl) ), Pyrrolyl (eg, 1-pyrrolyl), thiadiazolyl (eg, 1,3,4-thiadiazol-2-yl)]
6- to 14-membered carbocyclic group which may be substituted with 1 to 3 (preferably 1 or 2) substituents selected from [eg, phenyl, indanyl (eg, 2-indanyl, 5- Indanyl), naphthyl (eg, 1-naphthyl), fluorenyl (eg, 2-fluorenyl)],
(2) (a) a halogen atom (eg, fluorine atom, chlorine atom), and (b) an alkyl optionally substituted with 1 to 7 halogen atoms (eg, fluorine atom) (eg, methyl, isopropyl)
Biaryl optionally substituted with 1 to 3 (preferably 1 or 2) substituents selected from [eg, biphenylyl (eg, 4-biphenylyl, 3-biphenylyl), furylphenyl, pyrazolylthiazolyl , Thiadiazolylphenyl, phenyloxadiazolyl, thienylphenyl, pyrrolylphenyl], or (3) (a) alkyl (eg, methyl, ethyl, isopropyl),
(b) alkenyl (eg, 4-methyl-1-pentenyl),
(c) alkylcarbonyl (eg, acetyl),
(d) aryl (eg, phenyl), and (e) aromatic heterocyclic group (eg, pyrazolyl)
A 5- to 14-membered heterocyclic group optionally substituted with 1 to 3 (preferably 1 or 2) substituents selected from [eg, oxazolyl (eg, 4-oxazolyl), thiazolyl (eg, , 2-thiazolyl, 5-thiazolyl), thienyl (eg, 2-thienyl), oxadiazolyl (eg, [1,2,4] oxadiazol-5-yl), benzoimidazolyl (eg, 5-benzoimidazolyl), indolyl ( Example, 5-indolyl), dihydroindolyl (eg, 2,3-dihydroindol-5-yl, 2,3-dihydroindol-1-yl), benzothiazolyl (eg, 2-benzothiazolyl), carbazolyl (eg, 3) -Carbazolyl, 9-carbazolyl)]
And
B
(1) (a) a halogen atom (eg, chlorine atom),
(b) alkoxy (eg, methoxy),
(c) aryloxy (eg, phenoxy), and (d) arylalkoxyalkyl optionally substituted with alkyl (eg, isopropyl) (eg, benzyloxymethyl)
A divalent 6 to 14-membered carbocyclic group which may be substituted with 1 to 3 (preferably 1) substituents selected from [eg, phenylene (eg, 1,4-phenylene, 1 , 3-phenylene, 1,2-phenylene), indan-diyl (eg, indan-2,5-diyl), naphthylene (eg, 1,5-naphthylene)],
(2) Biarylene [eg, biphenylylene (eg, 4,4′-biphenylylene, 2,4′-biphenylylene), phenylpyridine-diyl, phenylpyrazole-diyl, phenylpyridazine-diyl, pyrazolylpyridazine-diyl], or (3 ) Divalent 5- to 14-membered heterocyclic group [eg, thiophene-diyl (eg, thiophene-2,5-diyl), oxadiazole-diyl (eg, [1,2,4] oxadiazole-3) , 5-diyl), pyridine-diyl (eg, pyridine-2,5-diyl), pyridazine-diyl (eg, pyridazine-3,6-diyl), benzofuran-diyl (eg, benzofuran-2,5-diyl, Benzofuran-2,6-diyl), indole-diyl (eg, indole-2,6-diyl), benzimidazole-diyl (eg, ben Zoimidazole-2,5-diyl), dihydroindole-diyl (eg, 2,3-dihydroindole-1,5-diyl), quinoline-diyl (eg, quinoline-3,7-diyl, quinoline-5,8) -Gille)]
And
C
(1) (a) a halogen atom (eg, fluorine atom, chlorine atom, bromine atom),
(b) hydroxy,
(c) carboxy,
(d) cyano,
(e) Nitro,
(f) amino,
(g) alkyl (eg, methyl, isopropyl),
(h) alkoxy (eg, methoxy), and (i) aryl (eg, phenyl)
6- to 14-membered carbocyclic group optionally substituted with 1 to 3 substituents selected from [eg, phenyl, indanyl (eg, 2-indanyl), naphthyl (eg, 1-naphthyl, 2- Naphthyl), fluorenyl (eg, 2-fluorenyl, 9-fluorenyl), azulenyl (eg, azulene-1-yl)],
(2) C _12-18 biaryl [eg, biphenylyl (eg, 4-biphenylyl, 2-biphenylyl)],
(3) arylalkyl optionally substituted with 1 to 3 halogen atoms (eg, chlorine atom) [eg, benzyl, naphthylethyl (eg, 2- (2-naphthyl) ethyl)],
(4) arylalkenyl [eg, naphthyl vinyl (eg, 2- (2-naphthyl) vinyl)],
(5) (a) hydroxy,
(b) alkoxy (eg butoxy),
(c) aryl optionally substituted with 1 to 3 halogen atoms (eg, chlorine atom) [eg, phenyl, naphthyl (eg, 2-naphthyl)], and (d) cycloalkyl (eg, cyclopropyl) Cyclohexyl)
C _1-12 alkyl (eg, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, dodecyl) optionally substituted by 1 to 3 (preferably 1) substituents selected from ),
(6) (a) aryl [eg, naphthyl (eg, 2-naphthyl)], and (b) aromatic heterocyclic group [eg, furanyl (eg, 2-furanyl)]
C _2-12 alkenyl (eg, vinyl, 1,3-butadienyl, hepta-1,3,5-triene) optionally substituted with 1 to 3 (preferably 1) substituents selected from -1-yl),
(7) C _3-10 cycloalkyl (eg, cyclopentyl, cyclohexyl),
(8) C _3-6 cycloalkyl-C _1-6 alkyl [eg, cyclohexylethyl (eg, 2-cyclohexylethyl), cyclopropylpropyl (eg, 3-cyclopropylpropyl), cyclopropylbutyl (eg, 4-cyclohexylethyl) Cyclopropylbutyl), cyclopropylpentyl (eg, 5-cyclopropylpentyl)],
(9) (a) Halogen atom (eg, chlorine atom), and (b) Alkyl (eg, methyl)
5- to 14-membered aromatic heterocyclic group optionally substituted with 1 to 3 (preferably 1 or 2) substituents selected from: [eg, thienyl (eg, 2-thienyl), isoxazolyl (Eg, 4-isoxazolyl), quinolyl (eg, 6-quinolyl), dibenzothiophenyl (eg, dibenzothiophen-2-yl)],
(10) an aromatic heterocyclic alkenyl (eg, furanyl-1,3-butadienyl), or (11) a 5- to 14-membered non-aromatic heterocyclic group [eg, azocanyl (eg, azocan-1-yl)] Yes,
X is
(1) alkylene (eg, methylene, ethylene, trimethylene) optionally substituted with 1 to 3 (preferably 1) arylalkyloxy (eg, benzyloxy),
(2) Alkenylene (eg, vinylene),
(3) alkynylene (eg, acetylene-1,2-diyl),
(4) (a) aryl (eg, phenyl), and (b) aromatic heterocyclic group [eg, thiazolyl (eg, 2-thiazolyl)]
* — (CH ₂ ) _m —O— (CH ₂ ) _n — ** (eg, —O) optionally substituted with 1 to 3 (preferably 1 or 2) substituents selected from -, * -CH ₂ -O-**, -CH ₂ -O-CH _2- , *-(CH ₂ ) ₂ -O-**),
(5) * — (CH ₂ ) _m —S (O) _p — (CH ₂ ) _n — ** (eg, —S—, —CH ₂ —S—CH ₂ —, —CH ₂ —SO—CH ₂ _{_{_{-, - CH 2 -SO 2 -CH}}} 2 -),
(6) **-(CH ₂ ) _m —CO— (CH ₂ ) _n — ** (eg, —CO—),
(7) * — (CH ₂ ) _q —CO—N (R ¹ ) — (CH ₂ ) _r — ** (eg, * —CH ₂ —CO—NH—CH ₂ — **), or (8) * —C (R ¹ ) ═N—O — ** (R ¹ is a hydrogen atom or lower alkyl (eg, methyl).)
(In the above (1) to (8), m, n, q and r each independently represent 0 or an integer of 1 to 4, p represents 0, 1 or 2, and * represents A And ** indicates the bonding position with B.)
And
Z is
(1) * -CONHSO ₂ -**,
(2) * -SO ₂ NHCO-**,
(3) * -NHCONHSO ₂ -**,
(4) * -CONHSO ₂ N (R ² )-** (R ² is a hydrogen atom or lower alkyl (eg, butyl)),
(5) * -CONCONHSO ₂ -** or (6) *-NHCONCONHSO ₂ -**
(In the above (1) to (6), * represents a bonding position with B, and ** represents a bonding position with C).

In another embodiment, the compound represented by formula (I) is preferably
A is an optionally substituted carbocyclic group, an optionally substituted biaryl, or an optionally substituted heterocyclic group;
B is a divalent carbocyclic group that may be substituted, a biarylene that may be substituted, or a divalent heterocyclic group that may be substituted;
C is an optionally substituted carbocyclic group, an optionally substituted biaryl, an optionally substituted arylalkyl, an optionally substituted arylalkenyl, an optionally substituted alkyl, a substituted An optionally substituted alkenyl, an optionally substituted cycloalkyl, an optionally substituted cycloalkylalkyl, an optionally substituted heterocyclic group, or an optionally substituted heterocyclic alkenyl,
X is an optionally substituted alkylene, an optionally substituted alkenylene, an optionally substituted alkynylene, an optionally substituted * — (CH ₂ ) _m —O— (CH ₂ ) _n — * *, Optionally substituted * — (CH ₂ ) _m —S (O) _p — (CH ₂ ) _n — **, optionally substituted * — (CH ₂ ) _m —N (R ¹ ) — (CH ₂ ) _n — **, optionally substituted * — (CH ₂ ) _m —CO— (CH ₂ ) _n — **, optionally substituted * — (CH ₂ ) _q —CO —N (R ¹ ) — (CH ₂ ) _r — **, or * —C (R ¹ ) = N—O — ** (where m, n, q and r are each independently 0 Or an integer of 1 to 4, p represents 0, 1 or 2, R ¹ represents a hydrogen atom or lower alkyl, and * represents A indicates a bonding position with A, and ** indicates a bonding position with B.)
Z is * -CONHSO ₂ -**, * -SO ₂ NHCO-**, * -N (R ² ) CONHSO ₂ -**, * -CONHSO ₂ N (R ² )-**, * -CONCONHSO ₂ -** or * -N (R ² ) COCONHSO ₂ -** (wherein R ² represents a hydrogen atom or lower alkyl, * represents a bonding position with B, ** represents a bonding position with C) Is a compound, and specifically,
A is
(1) (a) a halogen atom (eg, chlorine atom),
(b) Nitro,
(c) alkyl (eg, methyl, isopropyl, tert-butyl, hexyl) optionally substituted with 1 to 5 halogen atoms (eg, fluorine atom),
(d) alkenyl (eg, 2-methyl-1-propenyl, 4-methyl-1-pentenyl, 5-methyl-1-hexenyl),
(e) arylalkenyl [eg, phenyl vinyl (eg, 2-phenyl vinyl)],
(f) alkynyl (eg, ethynyl),
(g) arylalkynyl (eg, phenylethynyl),
(h) heterocyclic alkynyl [eg, thiazolylethynyl (eg, thiazol-5-ylethynyl)],
(i) alkoxy (eg, methoxy, isopropoxy),
(j) mono- or di-alkylamino (eg ethylamino, dimethylamino, diethylamino),
(k) cycloalkyl (eg, cyclobutyl),
(l) (i) a halogen atom (eg, fluorine atom, chlorine atom),
(ii) alkyl (eg, methyl, isopropyl) optionally substituted with 1 to 7 halogen atoms (eg, fluorine atom),
(iii) carboxy,
(iv) alkoxy (eg, methoxy),
(v) cyano,
(vi) nitro, and (vii) mono- or di-alkylamino (eg, dimethylamino)
Aryl (eg, phenyl) optionally substituted with 1 to 3 (preferably 1 or 2) substituents selected from
(m) Non-aromatic heterocyclic group [eg, pyrrolidinyl (eg, 1-pyrrolidinyl), dihydrobenzofuryl (eg, 2,3-dihydrobenzofuran-6-yl), benzodioxanyl (eg, 1,4- Benzodioxan-6-yl), benzodioxolyl (eg 1,3-benzodioxol-5-yl)],
(n) an aromatic heterocyclic group optionally substituted with alkyl (eg, methyl) optionally substituted with 1 to 7 halogen atoms (eg, fluorine atom) [eg, furyl (eg, 2- Furyl), thienyl (eg, 2-thienyl), pyrrolyl (eg, 1-pyrrolyl), thiadiazolyl (eg, 1,3,4-thiadiazol-2-yl), pyridyl (2-pyridyl), triazolyl (eg, 2H) -[1,2,3] -triazol-4-yl), oxazolyl (eg, isoxazol-5-yl)], and (o) aryloxy (eg, phenoxy)
A 5- to 14-membered carbocyclic group optionally substituted with 1 to 3 (preferably 1 or 2) substituents selected from: [eg, phenyl, indanyl (eg, 2-indanyl, 5- Indanyl), naphthyl (eg, 1-naphthyl), fluorenyl (eg, 2-fluorenyl, 9-fluorenyl), cyclopentyl],
(2) (a) a halogen atom (eg, fluorine atom, chlorine atom),
(b) alkyl (eg, methyl, isopropyl) optionally substituted with 1 to 7 halogen atoms (eg, fluorine atom),
(c) carboxy,
(d) alkoxy (eg, methoxy),
(e) cyano,
(f) nitro, and (g) mono- or di-alkylamino (eg, dimethylamino)
Biaryl optionally substituted with 1 to 3 (preferably 1 or 2) substituents selected from [eg, biphenylyl (eg, 4-biphenylyl, 3-biphenylyl), furylphenyl, pyrazolylthiazolyl , Thiadiazolylphenyl, phenyloxadiazolyl, thienylphenyl, pyrrolylphenyl, phenylpyridyl, pyridylphenyl, triazolylphenyl, oxazolylphenyl (eg, isoxazol-5-ylphenyl)], or (3 ) (A) alkyl (eg, methyl, ethyl, isopropyl),
(b) alkenyl (eg, 4-methyl-1-pentenyl),
(c) alkylcarbonyl (eg, acetyl),
(d) aryl (eg, phenyl), and (e) aromatic heterocyclic group (eg, pyrazolyl)
A 5- to 14-membered heterocyclic group optionally substituted with 1 to 3 (preferably 1 or 2) substituents selected from [eg, oxazolyl (eg, 4-oxazolyl), thiazolyl (eg, , 2-thiazolyl, 5-thiazolyl), thienyl (eg, 2-thienyl), oxadiazolyl (eg, [1,2,4] oxadiazol-5-yl), benzoimidazolyl (eg, 5-benzoimidazolyl), indolyl ( Example, 5-indolyl), dihydroindolyl (eg, 2,3-dihydroindol-5-yl, 2,3-dihydroindol-1-yl), benzothiazolyl (eg, 2-benzothiazolyl), carbazolyl (eg, 3) -Carbazolyl, 9-carbazolyl), pyridyl (eg, 2-pyridyl), benzoxazolyl (eg, 6-benzoxazolyl)]
And
B
(1) (a) a halogen atom (eg, chlorine atom),
(b) alkoxy (eg, methoxy),
(c) aryloxy (eg, phenoxy), and (d) arylalkoxyalkyl optionally substituted with alkyl (eg, isopropyl) (eg, benzyloxymethyl)
A divalent 6 to 14-membered carbocyclic group which may be substituted with 1 to 3 (preferably 1) substituents selected from [eg, phenylene (eg, 1,4-phenylene, 1 , 3-phenylene, 1,2-phenylene), indan-diyl (eg, indan-2,5-diyl), naphthylene (eg, 1,5-naphthylene)],
(2) Biarylene [eg, biphenylylene (eg, 4,4′-biphenylylene, 2,4′-biphenylylene), phenylpyridine-diyl, phenylpyrazole-diyl, phenylpyridazine-diyl, pyrazolylpyridazine-diyl], or (3 ) Divalent 5- to 14-membered heterocyclic group [eg, thiophene-diyl (eg, thiophene-2,5-diyl), oxadiazole-diyl (eg, [1,2,4] oxadiazole-3) , 5-diyl), pyridine-diyl (eg, pyridine-2,5-diyl), pyridazine-diyl (eg, pyridazine-3,6-diyl), benzofuran-diyl (eg, benzofuran-2,5-diyl, Benzofuran-2,6-diyl), indole-diyl (eg, indole-2,6-diyl), benzimidazole-diyl (eg, ben Zoimidazole-2,5-diyl), dihydroindole-diyl (eg, 2,3-dihydroindole-1,5-diyl), quinoline-diyl (eg, quinoline-3,7-diyl, quinoline-5,8) -Diyl), pyrrole-diyl (eg, pyrrole-1,3-diyl)]
And
C
(1) (a) a halogen atom (eg, fluorine atom, chlorine atom, bromine atom),
(b) hydroxy,
(c) carboxy,
(d) cyano,
(e) Nitro,
(f) amino,
(g) alkyl (eg, methyl, isopropyl),
(h) alkoxy (eg, methoxy), and (i) aryl (eg, phenyl)
6- to 14-membered carbocyclic group optionally substituted with 1 to 3 substituents selected from [eg, phenyl, indanyl (eg, 2-indanyl), naphthyl (eg, 1-naphthyl, 2- Naphthyl), fluorenyl (eg, 2-fluorenyl, 9-fluorenyl), azulenyl (eg, azulene-1-yl)],
(2) C _12-18 biaryl [eg, biphenylyl (eg, 4-biphenylyl, 2-biphenylyl)],
(3) arylalkyl optionally substituted with 1 to 3 halogen atoms (eg, chlorine atom) [eg, benzyl, naphthylethyl (eg, 2- (2-naphthyl) ethyl)],
(4) arylalkenyl [eg, naphthyl vinyl (eg, 2- (2-naphthyl) vinyl)],
(5) (a) hydroxy,
(b) alkoxy (eg butoxy),
(c) aryl optionally substituted with 1 to 3 halogen atoms (eg, chlorine atom) [eg, phenyl, naphthyl (eg, 2-naphthyl)],
(d) cycloalkyl (eg, cyclopropyl, cyclohexyl), and (e) an aromatic heterocyclic group optionally substituted with 1 to 3 alkyl groups (eg, methyl) [eg, oxadiazolyl (eg, [ 1,2,4] oxadiazol-5-yl)]
C _1-12 alkyl (eg, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, dodecyl) optionally substituted by 1 to 3 (preferably 1) substituents selected from ),
(6) (a) aryl [eg, naphthyl (eg, 2-naphthyl)], and (b) aromatic heterocyclic group [eg, furanyl (eg, 2-furanyl)]
C _2-12 alkenyl (eg, vinyl, 1,3-butadienyl, hepta-1,3,5-triene) optionally substituted with 1 to 3 (preferably 1) substituents selected from -1-yl),
(7) C _3-10 cycloalkyl (eg, cyclopentyl, cyclohexyl),
(8) C _3-6 cycloalkyl-C _1-6 alkyl [eg, cyclohexylethyl (eg, 2-cyclohexylethyl), cyclopropylpropyl (eg, 3-cyclopropylpropyl), cyclopropylbutyl (eg, 4-cyclohexylethyl) Cyclopropylbutyl), cyclopropylpentyl (eg, 5-cyclopropylpentyl)],
(9) (a) Halogen atom (eg, chlorine atom), and (b) Alkyl (eg, methyl)
5- to 14-membered aromatic heterocyclic group optionally substituted with 1 to 3 (preferably 1 or 2) substituents selected from: [eg, thienyl (eg, 2-thienyl), isoxazolyl (Eg, 4-isoxazolyl), quinolyl (eg, 6-quinolyl), dibenzothiophenyl (eg, dibenzothiophen-2-yl)],
(10) an aromatic heterocyclic alkenyl (eg, furanyl-1,3-butadienyl), or (11) a 5- to 14-membered non-aromatic heterocyclic group [eg, azocanyl (eg, azocan-1-yl)] Yes,
X is
(1) alkylene (eg, methylene, ethylene, trimethylene) optionally substituted with 1 to 3 (preferably 1) arylalkyloxy (eg, benzyloxy),
(2) Alkenylene (eg, vinylene),
(3) alkynylene (eg, acetylene-1,2-diyl),
(4) (a) aryl (eg, phenyl), and (b) 5- to 14-membered aromatic heterocyclic group [eg, thiazolyl (eg, 2-thiazolyl)]
* — (CH ₂ ) _m —O— (CH ₂ ) _n — ** which may be substituted with 1 to 3 (preferably 1 or 2) substituents selected from O—, * —CH ₂ —O — **, —CH ₂ —O—CH ₂ —, * — (CH ₂ ) ₂ —O — **, * —O—CH ₂ — **),
(5) * — (CH ₂ ) _m —S (O) _p — (CH ₂ ) _n — ** (eg, —S—, —CH ₂ —S—CH ₂ —, —CH ₂ —SO—CH ₂ _{_{_{-, - CH 2 -SO 2 -CH}}} 2 -),
(6) **-(CH ₂ ) _m —CO— (CH ₂ ) _n — ** (eg, —CO—),
(7) * — (CH ₂ ) _q —CO—N (R ¹ ) — (CH ₂ ) _r — ** (eg, * —CH ₂ —CO—NH—CH ₂ — **),
(8) *-C (R ¹ ) = NO — ** (where R ¹ is a hydrogen atom or lower alkyl (eg, methyl)), or (9) * — (CH ₂ ) _m —N (R ¹ ) — (CH ₂ ) _n — ** (eg, —CH ₂ —N (CH ₃ ) —CH ₂ —)
(In the above (1) to (9), m, n, q and r each independently represent 0 or an integer of 1 to 4, p represents 0, 1 or 2, and * represents A and (The bond position is indicated, and ** indicates the bond position with B.)
And
Z is
(1) * -CONHSO ₂ -**,
(2) * -SO ₂ NHCO-**,
(3) * -NHCONHSO ₂ -**,
(4) * -CONHSO ₂ N (R ² )-** (R ² is a hydrogen atom or lower alkyl (eg, butyl)),
(5) * -CONCONHSO ₂ -** or (6) *-NHCONCONHSO ₂ -**
(In the above (1) to (6), * represents a bonding position with B, and ** represents a bonding position with C).

The compound represented by the formula (I) is more preferably
A is an optionally substituted carbocyclic group or an optionally substituted heterocyclic group;
B is arylene which may be substituted;
C is an optionally substituted aryl or an optionally substituted aromatic heterocyclic group;
X is * —C (R ¹ ) ═N—O — ** (wherein R ¹ represents a hydrogen atom or lower alkyl, * represents a bonding position with A, and ** represents a bonding position with B) )
A compound in which Z is * -CONHSO ₂ -** (wherein * represents a bonding position with B and ** represents a bonding position with C), specifically,
A is
(1) (a) alkyl (eg, isopropyl, hexyl), and (b) mono- or di-alkylamino (eg, ethylamino, dimethylamino, diethylamino)
6- to 14-membered carbocyclic group optionally substituted by 1 to 3 (preferably 1 or 2) substituents selected from [eg, phenyl, indanyl (eg, 2-indanyl, 5- Indanyl)], or (2) (a) alkyl (eg, methyl, ethyl, isopropyl), and (b) alkylcarbonyl (eg, acetyl)
5- to 14-membered heterocyclic group optionally substituted by 1 to 3 (preferably 1 or 2) substituents selected from [eg, thienyl (eg, 2-thienyl), benzoimidazolyl (eg, , 5-benzimidazolyl), dihydroindolyl (eg, 2,3-dihydroindol-5-yl)]
And
B is C _6-14 arylene [eg, phenylene (eg, 1,4-phenylene)],
C
(1) (a) a halogen atom (eg, fluorine atom, chlorine atom, bromine atom),
(b) alkyl (eg, methyl, isopropyl), and (c) alkoxy (eg, methoxy)
C _6-14 aryl optionally substituted with 1 to 3 substituents selected from [eg phenyl], or (2) 1 to 3 (preferably 1 or 2) halogen atoms ( Eg, a 5- or 6-membered aromatic heterocyclic group optionally substituted with a chlorine atom [eg, thienyl (eg, 2-thienyl)]
And
X is * —C (R ¹ ) ═N—O — ** (wherein R ¹ is a hydrogen atom or lower alkyl (eg, methyl), * represents the bonding position with A, and ** represents B represents the bonding position with B).
A compound in which Z is * —CONHSO ₂ — ** (wherein, * represents a bonding position with B and ** represents a bonding position with C).

In another embodiment, the compound represented by formula (I) is more preferably
A is an optionally substituted carbocyclic group or an optionally substituted heterocyclic group;
B is arylene which may be substituted;
C is an optionally substituted aryl, an optionally substituted aromatic heterocyclic group, or an optionally substituted alkyl;
X is * —C (R ¹ ) ═N—O — ** (wherein R ¹ represents a hydrogen atom or lower alkyl, * represents a bonding position with A, and ** represents a bonding position with B) )
A compound in which Z is * -CONHSO ₂ -** (wherein * represents a bonding position with B and ** represents a bonding position with C), specifically,
A is
(1) (a) alkyl (eg, isopropyl, hexyl),
(b) mono- or di-alkylamino (eg ethylamino, dimethylamino, diethylamino),
(c) (i) alkyl (eg, methyl) optionally substituted with 1 to 7 halogen atoms (eg, fluorine atom),
(ii) Nitro,
(iii) mono- or di-alkylamino (eg, dimethylamino), and (iv) alkoxy (eg, methoxy)
Aryl (eg, phenyl) optionally substituted with 1 to 3 substituents selected from: (d) a non-aromatic heterocyclic group [eg, benzodioxanyl (eg, 1,4-benzo Dioxane-6-yl)]
6- to 14-membered carbocyclic group optionally substituted by 1 to 3 (preferably 1 or 2) substituents selected from [eg, phenyl, indanyl (eg, 2-indanyl, 5- Indanyl)], or (2) (a) alkyl (eg, methyl, ethyl, isopropyl), and (b) alkylcarbonyl (eg, acetyl)
5- to 14-membered heterocyclic group optionally substituted by 1 to 3 (preferably 1 or 2) substituents selected from [eg, thienyl (eg, 2-thienyl), benzoimidazolyl (eg, , 5-benzimidazolyl), dihydroindolyl (eg, 2,3-dihydroindol-5-yl)]
And
B is C _6-14 arylene [eg, phenylene (eg, 1,4-phenylene)],
C
(1) (a) a halogen atom (eg, fluorine atom, chlorine atom, bromine atom),
(b) alkyl (eg, methyl, isopropyl), and (c) alkoxy (eg, methoxy)
C _6-14 aryl optionally substituted with 1 to 3 substituents selected from [eg phenyl],
(2) 5- or 6-membered aromatic heterocyclic group optionally substituted with 1 to 3 (preferably 1 or 2) halogen atoms (eg, chlorine atom) [eg, thienyl (eg, 2) -Thienyl)], or (3) alkyl (eg, hexyl)
And
X is * —C (R ¹ ) ═N—O — ** (wherein R ¹ is a hydrogen atom or lower alkyl (eg, methyl), * represents the bonding position with A, and ** represents B represents the bonding position with B).
A compound in which Z is * —CONHSO ₂ — ** (wherein, * represents a bonding position with B and ** represents a bonding position with C).

In another embodiment, the compound represented by formula (I) is more preferably
A is an optionally substituted aryl, an optionally substituted biaryl, or an optionally substituted aromatic heterocyclic group;
B is an optionally substituted arylene or an optionally substituted divalent aromatic heterocyclic group;
C is an optionally substituted aryl, an optionally substituted biaryl, an optionally substituted arylalkyl, an optionally substituted arylalkenyl, an optionally substituted alkyl, an optionally substituted A good alkenyl, an optionally substituted cycloalkyl, an optionally substituted cycloalkylalkyl, an optionally substituted aromatic heterocyclic group, or an optionally substituted non-aromatic heterocyclic group,
X may be substituted * — (CH ₂ ) _m —O— (CH ₂ ) _n — **, or may be substituted * — (CH ₂ ) _m —S (O) _p — ( CH ₂ ) _n -** (wherein, m and n each independently represent an integer of 1 to 4, p represents 0 or 2, * represents a bonding position with A, and ** represents The bonding position to B.) (preferably —CH ₂ —O—CH ₂ — or —CH ₂ —S—CH ₂ —),
Z is * -CONHSO ₂ -**, * -SO ₂ NHCO-**, * -N (R ² ) CONHSO ₂ -**, * -CONHSO ₂ N (R ² )-**, * -CONCONHSO ₂ -**, or * -N (R ² ) COCONHSO ₂ -** (wherein R ² represents a hydrogen atom or lower alkyl, * represents a bonding position with B, ** represents a bond with C) Which indicates the position)), specifically,
A is
(1) (a) a halogen atom (eg, chlorine atom),
(b) Nitro,
(c) alkyl (eg, isopropyl, tert-butyl),
(d) alkenyl (eg, 2-methyl-1-propenyl, 4-methyl-1-pentenyl, 5-methyl-1-hexenyl),
(e) arylalkenyl [eg, phenyl vinyl (eg, 2-phenyl vinyl)],
(f) alkynyl (eg, ethynyl),
(g) heterocyclic alkynyl [eg, thiazoleethynyl (eg, thiazol-5-ylethynyl)],
(h) arylalkynyl (eg, phenylethynyl),
(i) alkoxy (eg, isopropoxy),
(j) cycloalkyl (eg, cyclobutyl),
(k) (i) a halogen atom (eg, fluorine atom, chlorine atom), and (ii) an alkyl optionally substituted with 1 to 3 halogen atoms (eg, fluorine atom) (eg, methyl)
Aryl (eg, phenyl) optionally substituted with 1 to 3 (preferably 1 or 2) substituents selected from
(l) non-aromatic heterocyclic group [eg, pyrrolidinyl (eg, 1-pyrrolidinyl)], and (m) aromatic heterocyclic group [eg, furyl (eg, 2-furyl), thienyl (eg, 2-thienyl) ), Pyrrolyl (eg, 1-pyrrolyl), thiadiazolyl (eg, 1,3,4-thiadiazol-2-yl)]
C _6-10 aryl optionally substituted by 1 to 3 (preferably 1 or 2) substituents selected from [eg, phenyl, naphthyl (eg, 1-naphthyl)],
(2) (a) a halogen atom (eg, fluorine atom, chlorine atom), and (b) an alkyl optionally substituted with 1 to 7 halogen atoms (eg, fluorine atom) (eg, methyl, isopropyl)
Biaryl optionally substituted with 1 to 3 (preferably 1 or 2) substituents selected from [eg, biphenylyl (eg, 4-biphenylyl), pyrazolylthiazolyl, thiadiazolylphenyl, Phenyloxadiazolyl, thienylphenyl, pyrrolylphenyl, furylphenyl], or (3) (a) alkyl (eg, methyl, isopropyl),
(b) alkenyl (eg, 4-methyl-1-pentenyl),
(c) aryl (eg, phenyl), and (d) aromatic heterocyclic group (eg, pyrazolyl)
5- to 14-membered aromatic heterocyclic group which may be substituted with 1 to 3 (preferably 1 or 2) substituents selected from [eg, oxazolyl (eg, 4-oxazolyl), thiazolyl (Eg, 2-thiazolyl, 5-thiazolyl), thienyl (eg, 2-thienyl), oxadiazolyl (eg, [1,2,4] oxadiazol-5-yl), benzothiazolyl (eg, 2-benzothiazolyl)] And
B
(1) (a) a halogen atom (eg, chlorine atom),
(b) alkoxy (eg, methoxy), and (c) aryloxy (eg, phenoxy)
C _6-10 arylene optionally substituted with 1 to 3 (preferably 1) substituents selected from [eg, phenylene (eg, 1,4-phenylene, 1,3-phenylene)] Or (2) a divalent aromatic heterocyclic group [eg, oxadiazole-diyl (eg, [1,2,4] oxadiazole-3,5-diyl), pyridazine-diyl (eg, pyridazine- 3,6-diyl), thiophene-diyl (eg, thiophene-2,5-diyl)]
C
(1) (a) a halogen atom (eg, chlorine atom, bromine atom),
(b) hydroxy,
(c) carboxy,
(d) cyano,
(e) Nitro,
(f) amino,
(g) aryl (eg, phenyl), and (h) alkyl (eg, methyl, isopropyl)
C _6-10 aryl optionally substituted with 1 to 3 substituents selected from [eg, phenyl, naphthyl (eg, 1-naphthyl, 2-naphthyl), azulenyl (eg, azulen-1-yl) )],
(2) Biaryl [eg, biphenylyl (eg, 4-biphenylyl, 2-biphenylyl)],
(3) C _6-10 aryl-C _1-6 alkyl optionally substituted by 1 to 3 (preferably 1 or 2) halogen atoms (eg, chlorine atom) [eg, benzyl, naphthylethyl (Eg, 2- (2-naphthyl) ethyl)],
(4) arylalkenyl [eg, naphthyl vinyl (eg, 2- (2-naphthyl) vinyl)],
(5) (a) hydroxy,
(b) alkoxy (eg butoxy),
(c) aryl optionally substituted with 1 to 3 halogen atoms (eg, chlorine atom) [eg, phenyl, naphthyl (eg, 2-naphthyl)], and (d) cycloalkyl (eg, cyclopropyl, Cyclohexyl)
C _1-12 alkyl (eg, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, dodecyl) optionally substituted by 1 to 3 (preferably 1) substituents selected from ),
(6) (a) aryl [eg, naphthyl (eg, 2-naphthyl)], and (b) aromatic heterocyclic group [eg, furanyl (eg, 2-furanyl)]
C _2-12 alkenyl optionally substituted with 1 to 3 (preferably 1) substituents selected from [eg, vinyl, 1,3-butadienyl, heptatrienyl (eg, hepta-1,3) , 5-trien-1-yl)],
(7) C _3-6 cycloalkyl (eg, cyclopentyl, cyclohexyl),
(8) C _3-6 cycloalkyl-C _1-6 alkyl (eg, 2-cyclohexylethyl, 3-cyclopropylpropyl, 4-cyclopropylbutyl, 5-cyclopropylpentyl),
(9) A 5- to 14-membered aromatic heterocyclic group optionally substituted by 1 to 3 (preferably 1 or 2) alkyl (eg, methyl) [eg, isoxazolyl (eg, 4-isoxazolyl) ), Quinolyl (eg, 6-quinolyl), dibenzothiophenyl (eg, dibenzothiophen-2-yl)], or (10) a 5- to 14-membered non-aromatic heterocyclic group [eg, azocanyl (eg, azocan- 1-yl)]
X is
(1) (a) aryl (eg, phenyl), and (b) aromatic heterocyclic group [eg, thiazolyl (eg, 2-thiazolyl)]
* — (CH ₂ ) _m —O— (CH ₂ ) _n — ** (eg, —CH ₂ —) which may be substituted with 1 to 3 (preferably 1) substituents selected from O—CH ₂ —), or (2) * — (CH ₂ ) _m —S (O) _p — (CH ₂ ) _n — ** (eg, —CH ₂ —S—CH ₂ — or —CH ₂ — SO ₂ —CH ₂ —),
Z is * -CONHSO ₂ -**, * -SO ₂ NHCO-**, * -CONHSO ₂ N (R ² )-**, * -NHCONHSO ₂ -**, * -CONCONHSO ₂ -**, or * —NHCOCONHSO ₂ — ** (R ² is a hydrogen atom or butyl).

In another embodiment, the compound represented by formula (I) is more preferably
A is an optionally substituted aryl, an optionally substituted biaryl, or an optionally substituted aromatic heterocyclic group;
B is an optionally substituted arylene or an optionally substituted divalent aromatic heterocyclic group;
C is an optionally substituted aryl, an optionally substituted biaryl, an optionally substituted arylalkyl, an optionally substituted arylalkenyl, an optionally substituted alkyl, an optionally substituted A good alkenyl, an optionally substituted cycloalkyl, an optionally substituted cycloalkylalkyl, an optionally substituted aromatic heterocyclic group, or an optionally substituted non-aromatic heterocyclic group,
X is optionally substituted * — (CH ₂ ) _m —O— (CH ₂ ) _n — **, optionally substituted * — (CH ₂ ) _m —S (O) _p — (CH ₂ ) _n -**, or optionally substituted *-(CH ₂ ) _m -N (R ¹ )-(CH ₂ ) _n -** (wherein m and n are each independently And represents an integer of 1 to 4, p represents 0 or 2, R ¹ represents a hydrogen atom or lower alkyl, * represents a bonding position with A, and ** represents a bonding position with B.) (Preferably —CH ₂ —O—CH ₂ —, —CH ₂ —S—CH ₂ — or —CH ₂ —N (CH ₃ ) —CH ₂ —),
Z is * -CONHSO ₂ -**, * -SO ₂ NHCO-**, * -N (R ² ) CONHSO ₂ -**, * -CONHSO ₂ N (R ² )-**, * -CONCONHSO ₂ -**, or * -N (R ² ) COCONHSO ₂ -** (wherein R ² represents a hydrogen atom or lower alkyl, * represents a bonding position with B, ** represents a bond with C) Which indicates the position)), specifically,
A is
(1) (a) a halogen atom (eg, chlorine atom),
(b) Nitro,
(c) alkyl (eg, isopropyl, tert-butyl),
(d) alkenyl (eg, 2-methyl-1-propenyl, 4-methyl-1-pentenyl, 5-methyl-1-hexenyl),
(e) arylalkenyl [eg, phenyl vinyl (eg, 2-phenyl vinyl)],
(f) alkynyl (eg, ethynyl),
(g) heterocyclic alkynyl [eg, thiazoleethynyl (eg, thiazol-5-ylethynyl)],
(h) arylalkynyl (eg, phenylethynyl),
(i) alkoxy (eg, methoxy, isopropoxy),
(j) cycloalkyl (eg, cyclobutyl),
(k) (i) a halogen atom (eg, fluorine atom, chlorine atom),
(ii) alkyl (eg, methyl) optionally substituted with 1 to 3 halogen atoms (eg, fluorine atom),
(iii) carboxy,
(iv) alkoxy (eg, methoxy),
(v) cyano,
(vi) nitro, and (vii) mono- or di-alkylamino (eg, dimethylamino)
Aryl (eg, phenyl) optionally substituted with 1 to 3 (preferably 1 or 2) substituents selected from
(l) Non-aromatic heterocyclic group [eg, pyrrolidinyl (eg, 1-pyrrolidinyl), dihydrobenzofuryl (eg, 2,3-dihydrobenzofuran-6-yl), benzodioxanyl (eg, 1,4- Benzodioxan-6-yl), benzodioxolyl (eg 1,3-benzodioxol-5-yl)],
(m) an aromatic heterocyclic group optionally substituted with alkyl (eg, methyl) optionally substituted with 1 to 7 halogen atoms (eg, fluorine atom) [eg, furyl (eg, 2- Furyl), thienyl (eg, 2-thienyl), pyrrolyl (eg, 1-pyrrolyl), thiadiazolyl (eg, 1,3,4-thiadiazol-2-yl), pyridyl (eg, 2-pyridyl), triazolyl (eg, 2H- [1,2,3] -triazol-4-yl), oxazolyl (eg, isoxazol-5-yl)], and (n) aryloxy (eg, phenoxy)
C _6-10 aryl optionally substituted with 1 to 3 (preferably 1 or 2) substituents selected from [eg, phenyl, naphthyl (eg, 1-naphthyl)],
(2) (a) a halogen atom (eg, fluorine atom, chlorine atom),
(b) alkyl (eg, methyl, isopropyl) optionally substituted with 1 to 7 halogen atoms (eg, fluorine atom),
(c) carboxy,
(d) alkoxy (eg, methoxy),
(e) cyano,
(f) nitro, and (g) mono- or di-alkylamino (eg, dimethylamino)
Biaryl optionally substituted with 1 to 3 (preferably 1 or 2) substituents selected from [eg, biphenylyl (eg, 4-biphenylyl), pyrazolylthiazolyl, thiadiazolylphenyl, Phenyloxadiazolyl, thienylphenyl, pyrrolylphenyl, furylphenyl, phenylpyridyl, pyridylphenyl, triazolylphenyl, oxazolylphenyl (eg, isoxazol-5-ylphenyl)],
(3) (a) alkyl (eg, methyl, isopropyl),
(b) alkenyl (eg, 4-methyl-1-pentenyl),
(c) aryl (eg, phenyl), and (d) aromatic heterocyclic group (eg, pyrazolyl)
5- to 14-membered aromatic heterocyclic group which may be substituted with 1 to 3 (preferably 1 or 2) substituents selected from [eg, oxazolyl (eg, 4-oxazolyl), thiazolyl (Eg, 2-thiazolyl, 5-thiazolyl), thienyl (eg, 2-thienyl), oxadiazolyl (eg, [1,2,4] oxadiazol-5-yl), benzothiazolyl (eg, 2-benzothiazolyl), Pyridyl (eg, 2-pyridyl), benzoxazolyl (eg, 6-benzoxazolyl)]
B
(1) (a) a halogen atom (eg, chlorine atom),
(b) alkoxy (eg, methoxy), and (c) aryloxy (eg, phenoxy)
C _6-10 arylene optionally substituted with 1 to 3 (preferably 1) substituents selected from [eg, phenylene (eg, 1,4-phenylene, 1,3-phenylene)] Or (2) a divalent aromatic heterocyclic group [eg, oxadiazole-diyl (eg, [1,2,4] oxadiazole-3,5-diyl), pyridazine-diyl (eg, pyridazine- 3,6-diyl), thiophene-diyl (eg, thiophene-2,5-diyl), pyridine-diyl (eg, pyridine-2,5-diyl)]
C
(1) (a) a halogen atom (eg, chlorine atom, bromine atom),
(b) hydroxy,
(c) carboxy,
(d) cyano,
(e) Nitro,
(f) amino,
(g) aryl (eg, phenyl), and (h) alkyl (eg, methyl, isopropyl)
C _6-10 aryl optionally substituted with 1 to 3 substituents selected from [eg, phenyl, naphthyl (eg, 1-naphthyl, 2-naphthyl), azulenyl (eg, azulen-1-yl) )],
(2) Biaryl [eg, biphenylyl (eg, 4-biphenylyl, 2-biphenylyl)],
(3) C _6-10 aryl-C _1-6 alkyl optionally substituted by 1 to 3 (preferably 1 or 2) halogen atoms (eg, chlorine atom) [eg, benzyl, naphthylethyl (Eg, 2- (2-naphthyl) ethyl)],
(4) arylalkenyl [eg, naphthyl vinyl (eg, 2- (2-naphthyl) vinyl)],
(5) (a) hydroxy,
(b) alkoxy (eg butoxy),
(c) aryl optionally substituted with 1 to 3 halogen atoms (eg, chlorine atom) [eg, phenyl, naphthyl (eg, 2-naphthyl)],
(d) cycloalkyl (eg, cyclopropyl, cyclohexyl), and (e) an aromatic heterocyclic group optionally substituted with 1 to 3 alkyl groups (eg, methyl) [eg, oxadiazolyl (eg, [ 1,2,4] oxadiazol-5-yl)]
C _1-12 alkyl (eg, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, dodecyl) optionally substituted by 1 to 3 (preferably 1) substituents selected from ),
(6) (a) aryl [eg, naphthyl (eg, 2-naphthyl)], and (b) aromatic heterocyclic group [eg, furanyl (eg, 2-furanyl)]
C _2-12 alkenyl optionally substituted with 1 to 3 (preferably 1) substituents selected from [eg, vinyl, 1,3-butadienyl, heptatrienyl (eg, hepta-1,3) , 5-trien-1-yl)],
(7) C _3-6 cycloalkyl (eg, cyclopentyl, cyclohexyl),
(8) C _3-6 cycloalkyl-C _1-6 alkyl (eg, 2-cyclohexylethyl, 3-cyclopropylpropyl, 4-cyclopropylbutyl, 5-cyclopropylpentyl),
(9) A 5- to 14-membered aromatic heterocyclic group optionally substituted by 1 to 3 (preferably 1 or 2) alkyl (eg, methyl) [eg, isoxazolyl (eg, 4-isoxazolyl) ), Quinolyl (eg, 6-quinolyl), dibenzothiophenyl (eg, dibenzothiophen-2-yl)], or (10) a 5- to 14-membered non-aromatic heterocyclic group [eg, azocanyl (eg, azocan- 1-yl)]
X is
(1) (a) aryl (eg, phenyl), and (b) aromatic heterocyclic group [eg, thiazolyl (eg, 2-thiazolyl)]
* — (CH ₂ ) _m —O— (CH ₂ ) _n — ** (eg, —CH ₂ —) which may be substituted with 1 to 3 (preferably 1) substituents selected from O—CH ₂ —),
(2) * — (CH ₂ ) _m —S (O) _p — (CH ₂ ) _n — ** (eg, —CH ₂ —S—CH ₂ — or —CH ₂ —SO ₂ —CH ₂ —), Or (3) * — (CH ₂ ) _m —N (R ¹ ) — (CH ₂ ) _n — ** (eg, —CH ₂ —N (CH ₃ ) —CH ₂ —),
Z is * -CONHSO ₂ -**, * -SO ₂ NHCO-**, * -CONHSO ₂ N (R ² )-**, * -NHCONHSO ₂ -**, * -CONCONHSO ₂ -**, or * —NHCOCONHSO ₂ — ** (R ² is a hydrogen atom or butyl).

In another embodiment, the compound represented by formula (I) is more preferably
A is an optionally substituted phenyl,
B is phenylene which may be substituted, or benzofuranylene which may be substituted;
C is an optionally substituted phenyl, an optionally substituted naphthyl, an optionally substituted alkyl, an optionally substituted cycloalkylalkyl, or an optionally substituted quinolyl;
X may be substituted * — (CH ₂ ) _m —O— (CH ₂ ) _n — ** or may be substituted * — (CH ₂ ) _m —S (O) _p — (CH ₂ ) _n -** (wherein, m and n each independently represents 0 or an integer of 1 to 4, p represents 0 or 2, * represents a bonding position with A, and ** represents B) (Preferably —O—, —CH ₂ —O—CH ₂ — or —CH ₂ —S—CH ₂ —),
Z is * -CONHSO ₂ -**, * -N (R ² ) CONHSO ₂ -**, * -CONHSO ₂ N (R ² )-**, * -CONCONSO ₂ -** or * -N (R ² ) COCONHSO ₂ -** (wherein R ² represents a hydrogen atom or optionally substituted lower alkyl, * represents a bonding position with Y, and ** represents a bonding position with C). (Preferably, * -CONHSO ₂ -**, * -NHCONHSO ₂ -**, * -CONHSO ₂ NH-**, * -CONCONHSO ₂ -** or * -NHCOCONHSO ₂ -**) ,In particular,
A is
(1) (a) a halogen atom (eg, chlorine atom),
(b) Nitro,
(c) alkyl (eg, methyl, isopropyl, tert-butyl) optionally substituted with 1 to 3 halogen atoms (eg, fluorine atom),
(d) alkenyl (eg, 2-methyl-1-propenyl, 4-methyl-1-pentenyl, 5-methyl-1-hexenyl),
(e) arylalkenyl [eg, phenyl vinyl (eg, 2-phenyl vinyl)],
(f) alkynyl (eg, ethynyl),
(g) heterocyclic alkynyl [eg, thiazolylethynyl (eg, thiazol-5-ylethynyl)],
(h) arylalkynyl (eg, phenylethynyl),
(i) alkoxy (eg, isopropoxy),
(j) cycloalkyl (eg, cyclobutyl),
(k) (i) a halogen atom (eg, fluorine atom, chlorine atom), and (ii) an alkyl optionally substituted with 1 to 3 halogen atoms (eg, fluorine atom) (eg, methyl, isopropyl)
Aryl (eg, phenyl) optionally substituted with 1 to 3 substituents selected from
(l) non-aromatic heterocyclic group [eg, pyrrolidinyl (eg, 1-pyrrolidinyl)], and (m) aromatic heterocyclic group [eg, furyl (eg, 2-furyl), thienyl (eg, 2-thienyl) ), Pyrrolyl (eg, 1-pyrrolyl), thiadiazolyl (eg, 1,3,4-thiadiazol-2-yl)]
Phenyl optionally substituted with 1 to 3 (preferably 1 or 2) substituents selected from
And
B
(1) (a) a halogen atom (eg, chlorine atom),
(b) alkoxy (eg, methoxy),
(c) aryloxy (eg, phenoxy), and (d) arylalkoxyalkyl optionally substituted with alkyl (eg, isopropyl) (eg, benzyloxymethyl)
Phenylene (eg, 1,4-phenylene, 1,3-phenylene) optionally substituted with 1 to 3 (preferably 1) substituents selected from: or (2) benzofuranylene [eg, Benzofuran-2,5-diyl, benzofuran-2,6-diyl, especially

(In the formula, * indicates a bonding position with X, and ** indicates a bonding position with Z.)]
And
C
(1) (a) a halogen atom (eg, chlorine atom, bromine atom),
(b) hydroxy,
(c) carboxy,
(d) cyano,
(e) Nitro,
(f) amino, and (g) aryl (eg, phenyl)
Phenyl optionally substituted with 1 to 3 substituents selected from
(2) naphthyl (eg, 1-naphthyl, 2-naphthyl) optionally substituted with 1 to 3 halogen atoms (eg, chlorine atom),
(3) (a) hydroxy,
(b) alkoxy (eg butoxy),
(c) aryl (eg, phenyl, naphthyl) optionally substituted with 1 to 3 halogen atoms (eg, chlorine atom), and (d) cycloalkyl (eg, cyclohexyl)
C _1-12 alkyl (eg, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, dodecyl) optionally substituted by 1 to 3 (preferably 1) substituents selected from ),
(4) C _3-6 cycloalkyl-C _1-6 alkyl (eg, 2-cyclohexylethyl, 3-cyclopropylpropyl, 4-cyclopropylbutyl, 5-cyclopropylpentyl), or (5) quinolyl (eg, 6-quinolyl)
And
X is
(1) (a) aryl (eg, phenyl), and (b) aromatic heterocyclic group [eg, thiazolyl, (eg, 2-thiazolyl)]
* — (CH ₂ ) _m —O— (CH ₂ ) _n — ** (eg, —CH ₂ —) which may be substituted with 1 to 3 (preferably 1) substituents selected from O—CH ₂ —, * — (CH ₂ ) ₂ —O — **, —O—), or (2) * — (CH ₂ ) _m —S (O) _p — (CH ₂ ) _n — ** _{_{(eg, -S -, - CH 2 -S}} -CH 2 -, - CH 2 -SO 2 -CH 2 -) a,
Z is * -CONHSO ₂ -**, * -N (R ² ) CONHSO ₂ -** (eg, * -NHCONHSO ₂ -**), * -CONHSO ₂ N (R ² )-** (eg, * -CONHSO ₂ NH-**, * -CONHSO ₂ N (Bu)-**), * -SO ₂ NHCO-**, * -COCONHSO ₂ -**, or * -N (R ² ) COCONHSO _2- ** (eg, * -NHCOCONHSO ₂ -**) (wherein R ² represents a hydrogen atom or lower alkyl, * represents a bonding position with B, and ** represents a bonding position with C). ) (Preferably * -CONHSO ₂ -**).

In still another embodiment, the compound represented by formula (I) is more preferably
A is an optionally substituted phenyl,
B is phenylene which may be substituted, or benzofuranylene which may be substituted;
C is an optionally substituted phenyl, an optionally substituted naphthyl, an optionally substituted alkyl, an optionally substituted cycloalkylalkyl, or an optionally substituted quinolyl;
X is optionally substituted * — (CH ₂ ) _m —O— (CH ₂ ) _n — **, optionally substituted * — (CH ₂ ) _m —S (O) _p — (CH ₂ ) _n -**, or optionally substituted *-(CH ₂ ) _m -N (R ¹ )-(CH ₂ ) _n -** (wherein m and n are each independently 0 or An integer of 1 to 4, p represents 0 or 2, R ¹ represents a hydrogen atom or lower alkyl, * represents a bonding position with A, and ** represents a bonding position with B). Preferred is —O—, —CH ₂ —O—CH ₂ —, —CH ₂ —S—CH ₂ — or —CH ₂ —N (CH ₃ ) —CH ₂ —),
Z is * -CONHSO ₂ -**, * -N (R ² ) CONHSO ₂ -**, * -CONHSO ₂ N (R ² )-**, * -CONHSO ₂ -**, or * -N ( R ² ) COCONHSO ₂ -** (wherein R ² represents a hydrogen atom or an optionally substituted lower alkyl, * represents a bonding position with Y, and ** represents a bonding position with C). ) (Preferably, * -CONHSO ₂ -**, * -NHCONHSO ₂ -**, * -CONHSO ₂ NH-**, * -COCONHSO ₂ -**, or * -NHCOCONHSO ₂ -**) Specifically,
A is
(1) (a) a halogen atom (eg, chlorine atom),
(b) Nitro,
(c) alkyl (eg, isopropyl, tert-butyl),
(d) alkenyl (eg, 2-methyl-1-propenyl, 4-methyl-1-pentenyl, 5-methyl-1-hexenyl),
(e) arylalkenyl [eg, phenyl vinyl (eg, 2-phenyl vinyl)],
(f) alkynyl (eg, 1-propynyl),
(g) heterocyclic alkynyl [eg, thiazoleethynyl (eg, thiazol-5-ylethynyl)],
(h) arylalkynyl (eg, phenylethynyl),
(i) alkoxy (eg, methoxy, isopropoxy),
(j) cycloalkyl (eg, cyclobutyl),
(k) (i) a halogen atom (eg, fluorine atom, chlorine atom),
(ii) Alkyl (eg, methyl) optionally substituted with 1 to 3 halogen atoms (eg, fluorine atom)
(iii) carboxy,
(iv) alkoxy (eg, methoxy),
(v) cyano,
(vi) nitro, and (vii) mono- or di-alkylamino (eg, dimethylamino)
Aryl (eg, phenyl) optionally substituted with 1 to 3 substituents selected from
(l) Non-aromatic heterocyclic group [eg, pyrrolidinyl (eg, 1-pyrrolidinyl), dihydrobenzofuryl (eg, 2,3-dihydrobenzofuran-6-yl), benzodioxolyl (eg, 1,3- Benzodioxol-5-yl)],
(m) an aromatic heterocyclic group optionally substituted with alkyl (eg, methyl) optionally substituted with 1 to 7 halogen atoms (eg, fluorine atom) [eg, furyl (eg, 2- Furyl), thienyl (eg, 2-thienyl), pyrrolyl (eg, 1-pyrrolyl), thiadiazolyl (eg, 1,3,4-thiadiazol-2-yl), pyridyl (eg, 2-pyridyl), triazolyl (eg, 2H- [1,2,3] triazol-4-yl), oxazolyl (eg, isoxazol-5-yl)], and (n) aryloxy (eg, phenoxy)
Phenyl optionally substituted with 1 to 3 (preferably 1 or 2) substituents selected from
B
(1) (a) a halogen atom (eg, chlorine atom),
(b) Alkoxy (eg, methoxy)
(c) aryloxy (eg, phenoxy), and (d) arylalkoxyalkyl optionally substituted with alkyl (eg, isopropyl) (eg, benzyloxymethyl)
Phenylene (eg, 1,4-phenylene, 1,3-phenylene) optionally substituted with 1 to 3 (preferably 1) substituents selected from: or (2) benzofuranylene [eg, Benzofuran-2,5-diyl, benzofuran-2,6-diyl, especially

(In the formula, * indicates a bonding position with X, and ** indicates a bonding position with Z.)]
And
C
(1) (a) a halogen atom (eg, chlorine atom, bromine atom),
(b) hydroxy,
(c) carboxy,
(d) cyano,
(e) Nitro,
(f) amino, and (g) aryl (eg, phenyl)
Phenyl optionally substituted with 1 to 3 substituents selected from
(2) naphthyl (eg, 1-naphthyl, 2-naphthyl) optionally substituted with 1 to 3 halogen atoms (eg, chlorine atom),
(3) (a) hydroxy,
(b) alkoxy (eg butoxy),
(c) aryl (eg, phenyl, naphthyl) optionally substituted by 1 to 3 halogen atoms (eg, chlorine atom),
(d) cycloalkyl (eg, cyclohexyl), and (e) an aromatic heterocyclic group optionally substituted with 1 to 3 alkyl groups (eg, methyl) [eg, oxadiazolyl (eg, [1,2 , 4] oxadiazol-5-yl)]
C _1-12 alkyl (eg, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, dodecyl) optionally substituted by 1 to 3 (preferably 1) substituents selected from ),
(4) C _3-6 cycloalkyl-C _1-6 alkyl (eg, 2-cyclohexylethyl, 3-cyclopropylpropyl, 4-cyclopropylbutyl, 5-cyclopropylpentyl), or (5) quinolyl (eg, 6-quinolyl)
And
X is
(1) (a) aryl (eg, phenyl), and (b) aromatic heterocyclic group [eg, thiazolyl (eg, 2-thiazolyl)]
* — (CH ₂ ) _m —O— (CH ₂ ) _n — ** (eg, —CH ₂ —) which may be substituted with 1 to 3 (preferably 1) substituents selected from O—CH ₂ —, * — (CH ₂ ) ₂ —O — **, —O—),
(2) * — (CH ₂ ) _m —S (O) _p — (CH ₂ ) _n — ** (eg, —S—, —CH ₂ —S—CH ₂ —, —CH ₂ —SO ₂ —CH _2- ), or (3) *-(CH ₂ ) _m —N (R ¹ ) — (CH ₂ ) _n — ** (eg, —CH ₂ —N (CH ₃ ) —CH ₂ —),
Z is * -CONHSO ₂ -**, * -N (R ² ) CONHSO ₂ -** (eg, * -NHCONHSO ₂ -**), * -CONHSO ₂ N (R ² )-** (eg, * -CONHSO ₂ NH-**, * -CONHSO ₂ N (Bu)-**), * -SO ₂ NHCO-**, * -COCONHSO ₂ -**, or * -N (R ² ) COCONHSO _2- ** (eg, * -NHCOCONHSO ₂ -**) (wherein R ² represents a hydrogen atom or lower alkyl, * represents a bonding position with B, and ** represents a bonding position with C). ) (Preferably * -CONHSO ₂ -**).

The compound represented by the formula (I) is particularly preferably
(1) N- [4- (biphenyl-4-ylmethylsulfanylmethyl) benzoyl] octane-1-sulfonamide,

(2) N- [4- (biphenyl-4-ylmethoxymethyl) benzoyl] -2,4-dichlorobenzenesulfonamide,

(3) N- [4- (biphenyl-4-ylmethoxymethyl) benzoyl] octane-1-sulfonamide,

(4) N- [4- (biphenyl-4-ylmethylsulfanylmethyl) benzoyl] hexane-1-sulfonamide,

(5) N- [4- (biphenyl-4-ylmethylsulfanylmethyl) benzoyl] -4-cyclopropylbutane-1-sulfonamide,

(6) N- [4- (biphenyl-4-ylmethoxymethyl) benzoyl] heptane-1-sulfonamide,

(7) N- [4- (biphenyl-4-ylmethoxymethyl) benzoyl] -5-cyclopropylpentane-1-sulfonamide,

(1 ') 4- (4-Isopropylbenzyloxymethyl) -N- (heptylaminosulfonyl) benzamide,

(2 ') N- {2- [4- (4-isopropylbenzyloxymethyl) phenyl] -2-oxoacetyl} octane-1-sulfonamide,

(3 ') N- [4- (4-isopropylbenzyloxymethyl) phenyl] -2- (octane-1-sulfonylamino) -2-oxoacetamide,

(4 ') N- [4- (biphenyl-4-ylmethylsulfanylmethyl) phenyl] -2- (hexane-1-sulfonylamino) -2-oxoacetamide,

Or (5 ′) N- {2- [4- (biphenyl-4-ylmethylsulfanylmethyl) phenyl] -2-oxoacetyl} hexane-1-sulfonamide

It is.
In another embodiment, the compound represented by formula (I) is particularly preferably
(1) (1) N- [4- (3′-methoxybiphenyl-4-ylmethylsulfanylmethyl) benzoyl] hexane-1-sulfonamide,

(2) N- {4- [3 '-(trifluoromethyl) biphenyl-4-ylmethylsulfanylmethyl] benzoyl} hexane-1-sulfonamide,

(3) N- {4- [4- (1,4-benzodioxan-6-yl) benzylsulfanylmethyl] benzoyl} hexane-1-sulfonamide,

(4) N- {4- [3 '-(trifluoromethyl) biphenyl-4-ylmethoxymethyl] benzoyl} hexane-1-sulfonamide,

(5) N- [4- (3'-methoxybiphenyl-3-ylmethylsulfanylmethyl) benzoyl] hexane-1-sulfonamide,

(6) (E) -N-({4- [3 '-(trifluoromethyl) biphenyl-4-yl] methyleneaminooxy} benzoyl) hexane-1-sulfonamide,

(7) (E) -N-({4- [4- (1,4-benzodioxan-6-yl) phenyl] methyleneaminooxy} benzoyl) hexane-1-sulfonamide,

(8) (E) -N- [4- (3'-dimethylaminobiphenyl-4-ylmethyleneaminooxy) benzoyl] hexane-1-sulfonamide,

(9) (E) -N- [4- (3'-methoxybiphenyl-4-ylmethyleneaminooxy) benzoyl] hexane-1-sulfonamide,

(10) N-{[4- (3'-methoxybiphenyl-4-ylmethylsulfanylmethyl) phenyl] -2-oxoacetyl} hexane-1-sulfonamide

Or (11) N-({4- [4- (1,4-benzodioxan-6-yl) benzylsulfanylmethyl] phenyl} -2-oxoacetyl) hexane-1-sulfonamide

It is.
Compound (I) of the present invention may form a pharmaceutically acceptable salt. The pharmaceutically acceptable salt in this specification may be any salt as long as it is a pharmaceutically non-toxic salt. When compound (I) has a basic group, it can form an acid addition salt. As an acid for forming such an acid addition salt, it can form a salt with a basic moiety, and can be a pharmaceutical. There is no particular limitation as long as the acid is acceptable. Examples of such acids include inorganic acids such as hydrochloric acid, sulfuric acid, phosphoric acid and nitric acid, and organic acids such as oxalic acid, fumaric acid, maleic acid, citric acid, tartaric acid, methanesulfonic acid and toluenesulfonic acid. When compound (I) has an acidic group such as a carboxy group, for example, an alkali metal salt (for example, sodium salt, potassium salt), an alkaline earth metal salt (for example, calcium salt, magnesium salt), an organic base Salts (eg, triethylamine salts, dicyclohexylamine salts, pyridine salts, etc.) can be formed.

(Method for producing the compound of the present invention)
The compound represented by the general formula (I) of the present invention and a pharmaceutically acceptable salt thereof can be produced by any of the following production methods.

(Production method 1)

[Wherein, A, B, C and X are as defined above. ]

Production method 1 is a method for producing a compound (Ia) in which, in the general formula (I), Z is * -CONHSO ₂ -** (wherein * and ** are as defined above). is there.
Production method 1 is a method for producing compound (Ia) by subjecting compound (1) to an amidation reaction.
This reaction is carried out using a method known per se, for example, a method of directly condensing compound (1) and compound (2) or a method of reacting a reactive derivative of compound (1) with compound (2). Done.

The method of directly condensing the compound (1) and the compound (2) is performed in the presence of a condensing agent in a solvent that does not adversely influence the reaction. Examples of the condensing agent include N, N′-dicyclohexylcarbodiimide, 1-ethyl-3- (3′-dimethylaminopropyl) carbodiimide, N-cyclohexyl-N′-morpholinoethylcarbodiimide, N-cyclohexyl-N ′-(4 Carbodiimide compounds such as -diethylaminocyclohexyl) carbodiimide; azolide compounds such as N, N'-carbonyldiimidazole and N, N'-thionyldiimidazole; condensing agents such as phosphorus compounds such as diethyl cyanophosphate and diphenylphosphoryl azide It is done.
Specific examples of solvents that do not adversely affect the reaction include acetone, dioxane, acetonitrile, chloroform, benzene, toluene, methylene chloride, ethylene chloride, tetrahydrofuran, ethyl acetate, N, N′-dimethylformamide, pyridine, water, and the like. And the like.

The amount of compound (2) to be used is generally 1 to 5 mol, preferably 1 to 3 mol, per 1 mol of compound (1).
The amount of the condensing agent to be used is generally 1 to 5 mol, preferably 1 to 3 mol, per 1 mol of compound (1).

When the carbodiimide compound is used as a condensing agent, a condensation accelerator (for example, 1-hydroxy-7-azabenzotriazole, 1-hydroxybenzotriazole, N-hydroxysuccinimide, N-hydroxyphthalimide, etc.) is optionally used. By using it, the reaction yield can be improved. When the above phosphorus compound is used as a condensing agent, the reaction yield can be improved by adding an organic base such as triethylamine or N, N-diisopropylethylamine as necessary. Further, when the above azolide compound is used as a condensing agent, triethylamine, N, N-diisopropylethylamine, N-methylmorpholine, 4-dimethylaminopyridine, 1,8-diazabicyclo [5,4,0] undec-7-ene, etc. It is desirable to carry out the reaction in the presence of a base such as an alkali metal carbonate such as sodium carbonate, sodium hydrogen carbonate, potassium carbonate, potassium hydrogen carbonate, or cesium carbonate.

The amount of the condensation accelerator, organic base and alkali metal carbonate used is usually 1 to 5 mol, preferably 1 to 3 mol, per 1 mol of compound (1).
Reaction conditions such as reaction temperature and reaction time vary depending on the reaction reagent and reaction solvent used, but the reaction temperature is usually from −30 to 150 ° C., and the reaction time is from 30 minutes to 20 hours.

In the method of reacting the reactive derivative of compound (1) with compound (2), examples of the reactive derivative of compound (1) include acid halides such as acid chloride and acid bromide; acid anhydrides; dialkyl phosphoric acid Such as substituted phosphoric acid, mixed acid anhydride with chlorocarbonate such as methyl chlorocarbonate, ethyl chlorocarbonate or isobutyl chlorocarbonate; active amide with imidazole; ester such as cyanomethyl ester, 4-nitrophenyl ester, etc. Can be mentioned.

When the above acid halide is used as the reactive derivative of compound (1), it is usually carried out in the presence of a base in a solvent that does not adversely influence the reaction.
The base used in the reaction is not particularly limited, and is an organic base such as triethylamine, N, N-diisopropylethylamine, N-methylmorpholine, 4-dimethylaminopyridine; sodium carbonate, sodium hydrogen carbonate, potassium carbonate, hydrogen carbonate Examples include alkali metal carbonates such as potassium and cesium carbonate.
Specific examples of solvents that do not adversely affect the reaction include acetone, dioxane, acetonitrile, chloroform, benzene, toluene, methylene chloride, ethylene chloride, tetrahydrofuran, ethyl acetate, N, N′-dimethylformamide, pyridine, water, and the like. And the like.

The amount of compound (2) to be used is generally 1 to 5 mol, preferably 1 to 3 mol, per 1 mol of compound (1).
Reaction conditions such as reaction temperature and reaction time vary depending on the reaction reagent and reaction solvent used, but the reaction temperature is usually from −30 to 150 ° C., and the reaction time is from 30 minutes to 20 hours.

When a mixed acid anhydride is used as the reactive derivative of compound (1), compound (1) and substituted phosphoric acid or chlorocarbonate are converted to a base (eg, triethylamine, N, N-diisopropylethylamine, N-methylmorpholine, N , N-dimethylaniline, etc .; alkali metal carbonates such as sodium hydrogen carbonate, sodium carbonate, potassium carbonate, etc.) to make a reactive derivative, and further react with compound (2).
The amount of compound (2) to be used is generally 1 to 5 mol, preferably 1 to 3 mol, per 1 mol of compound (1).

Reaction conditions such as reaction temperature and reaction time vary depending on the reaction reagent and reaction solvent used, but the reaction temperature is usually from −30 to 150 ° C., and the reaction time is from 30 minutes to 20 hours.
Compound (1) used in this production method can be produced according to the method described in production methods 8 to 13 or a method analogous thereto. It can also be obtained as a commercial product.
Compound (2) used in this production method can be obtained as a commercial product, or can be produced according to a method known per se or a method analogous thereto.

(Manufacturing method 2)

[Wherein, A, B, C and X are as defined above. ]

Production method 2 is a method for producing compound (Ib) in which, in general formula (I), Z is * -SO ₂ NHCO-** (wherein * and ** are as defined above). It is.
Compound (Ib) can be produced by subjecting compound (3) and compound (4) to a reaction similar to the amidation reaction described in Production Method 1.
Compound (3) and compound (4) used in this production method can be obtained as commercially available products, or can be produced according to a method known per se or a method analogous thereto.

(Manufacturing method 3)

[Wherein, A, B, C, X and R ² are as defined above. ]

In the production method 3, in general formula (I), Z is * —CONHSO ₂ N (R ² ) — ** (wherein R ² , * and ** are as defined above) (I -C).
Compound (Ic) can be produced by subjecting compound (1) and compound (5) to a reaction similar to the amidation reaction described in Production Method 1.
Compound (5) used in this production method can be obtained as a commercially available product, or can be produced according to a method known per se or a method analogous thereto.

(Manufacturing method 4)
(Production method 4-A)

[Wherein, A, B, C, X and R ² are as defined above, and L ¹ and L ² each independently represent hydroxy, halogen atoms (for example, fluorine atom, chlorine atom, bromine atom) , Iodine atom), imidazolyl, succinimideoxy, alkanesulfonyloxy (eg, methanesulfonyloxy, ethanesulfonyloxy, propanesulfonyloxy, trifluoromethanesulfonyloxy, etc.) or arylsulfonyloxy (eg, benzenesulfonyloxy, tolylsulfonyloxy, etc.) And the like. ]

In the production method 4-A, in general formula (I), Z is * —N (R ² ) CONHSO ₂ — ** (wherein R ² , * and ** are as defined above). This is a method for producing (Id).
This production method is a method known per se, for example, after reacting compound (6) and compound (7) in a solvent that does not affect the reaction, the resulting compound and compound (2) are reacted. The reaction is carried out in a solvent that does not affect the reaction. In addition, this reaction is carried out by using an organic base such as triethylamine, N, N-diisopropylethylamine, N-methylmorpholine, 4-dimethylaminopyridine, 1,8-diazabicyclo [5,4,0] undec-7-ene; sodium carbonate The reaction may be carried out in the presence of a base such as an alkali metal carbonate such as sodium hydrogen carbonate, potassium carbonate, potassium hydrogen carbonate or cesium carbonate.

Specific examples of solvents that do not adversely affect the reaction include acetone, dioxane, acetonitrile, chloroform, benzene, toluene, methylene chloride, ethylene chloride, tetrahydrofuran, ethyl acetate, N, N′-dimethylformamide, pyridine, water, and the like. And the like.
Examples of the compound (7) include N, N′-carbonyldiimidazole, diphosgene, triphosgene and the like.
The amount of compound (7) to be used is generally 1 to 5 mol, preferably 1 to 3 mol, per 1 mol of compound (6).
The amount of compound (2) to be used is generally 1 to 5 mol, preferably 1 to 3 mol, per 1 mol of compound (6).
Reaction conditions such as reaction temperature and reaction time vary depending on the reaction reagent and reaction solvent used, but the reaction temperature is usually from −30 to 150 ° C., and the reaction time is from 30 minutes to 20 hours.
Compound (2), compound (6) and compound (7) used in this production method can be obtained as commercial products, or can be produced according to a method known per se or a method analogous thereto.

(Production method 4-B)

[Wherein, A, B, C, X and R ² are as defined above. ]

In the production method 4-B, in general formula (I), Z is * —N (R ² ) CONHSO ₂ — ** (wherein R ² , * and ** are as defined above). This is a method for producing (Id).
This production method is carried out by a method known per se, for example, by reacting compound (6) and compound (8) in a solvent that does not affect the reaction. In addition, this reaction is carried out by using an organic base such as triethylamine, N, N-diisopropylethylamine, N-methylmorpholine, 4-dimethylaminopyridine, 1,8-diazabicyclo [5,4,0] undec-7-ene; sodium carbonate The reaction may be carried out in the presence of a base such as an alkali metal carbonate such as sodium hydrogen carbonate, potassium carbonate, potassium hydrogen carbonate or cesium carbonate.
Specific examples of solvents that do not adversely affect the reaction include acetone, dioxane, acetonitrile, chloroform, benzene, toluene, methylene chloride, ethylene chloride, tetrahydrofuran, ethyl acetate, N, N′-dimethylformamide, pyridine, water, and the like. And the like.
The amount of compound (8) to be used is generally 1 to 5 mol, preferably 1 to 3 mol, per 1 mol of compound (6).
Reaction conditions such as reaction temperature and reaction time vary depending on the reaction reagent and reaction solvent used, but the reaction temperature is usually from −30 to 150 ° C., and the reaction time is from 30 minutes to 20 hours.
Compound (6) and compound (8) used in this production method can be obtained as commercially available products, or can be produced according to a method known per se or a method analogous thereto.

(Production method 4-C)

[Wherein, A, B, C and X are as defined above. ]

Process 4-C produces compound (Ie) in which general formula (I) is such that Z is * -NHCONHSO ₂ -** (wherein * and ** are as defined above). Is the method.
This production method is produced by heating an acid azide obtained by reacting compound (1) with diphenylphosphoric acid azide (DPPA) in the presence of a base such as triethylamine in a solvent that does not affect the reaction. This is carried out by reacting the isocyanate compound with the compound (2).
Specific examples of solvents that do not adversely affect the reaction include acetone, dioxane, acetonitrile, chloroform, benzene, toluene, methylene chloride, ethylene chloride, tetrahydrofuran, ethyl acetate, N, N′-dimethylformamide, pyridine, and mixtures thereof. Etc.
The amount of DPPA to be used is generally 1-5 mol, preferably 1-3 mol, per 1 mol of compound (1).
Reaction conditions such as reaction temperature and reaction time vary depending on the reaction reagent and reaction solvent used, but in the step of reacting compound (1) with DPPA to obtain isocyanate, the reaction temperature is usually from −30 to 110 ° C. Yes, the reaction time is from 30 minutes to 20 hours. In the step of reacting the isocyanate compound with compound (2), the reaction temperature is usually −30 to 50 ° C., and the reaction time is 30 minutes to 20 hours.

(Manufacturing method 5)

[Wherein, A, B, C, X and R ² are as defined above. ]

Production method 5 is a compound in which Z is * —N (R ² ) SO ₂ NHCO — ** (wherein R ² , * and ** are as defined above) in general formula (I). If)).
Compound (If) can be produced by subjecting compound (4) and compound (9) to a reaction similar to the amidation reaction described in Production Method 1.
Compound (9) and compound (4) used in this production method can be obtained as commercially available products, or can be produced according to a method known per se or a method analogous thereto.

(Production method 6)

[Wherein, A, B, C, X, R ² , L ¹ and L ² are as defined above. ]

In Production Method 6, in general formula (I), Z is * —SO ₂ NHCON (R ² ) — ** (wherein R ² , * and ** are as defined above). -G).
Compound (Ig) is produced by reacting compound (10) with compound (7) and then subjecting the resulting compound and compound (3) to a reaction similar to the reaction described in Production Method 4. be able to.
Compound (3), compound (7) and compound (10) used in this production method can be obtained as commercial products, or can be produced according to a method known per se or a method analogous thereto.

(Manufacturing method 7)

Wherein A, B, C and R ¹ are as defined above, R ³ represents lower alkyl,
L ³ represents a leaving group such as hydroxy or a halogen atom (eg, fluorine atom, chlorine atom, bromine atom, iodine atom), and Z represents * -CONHSO ₂ -** or * -CONHSO ₂ N (R ² )-** (wherein R ² , * and ** are as defined above). ]

In the production method 7, in general formula (I), X is * —C (R ¹ ) = N—O — ** (wherein R ¹ , * and ** are as defined above), And Z is * -CONHSO ₂ -** or * -CONHSO ₂ N (R ² )-** (wherein R ² , * and ** are as defined above) (Ih) ).
Compound (15) is reacted with Compound (11) and ethyl N-hydroxyacetimidate in a solvent that does not affect the reaction in the presence of a base such as calcium tert-butoxide to obtain Compound (12). Then, it is reacted with compound (13) and perchloric acid to obtain compound (14), which can be produced by hydrolyzing the ester of compound (14) by a method known per se.

Compound (Ih) wherein Z is * -CONHSO ₂ -** or * -CONHSO ₂ N (R ² )-** (wherein R ² , * and ** are as defined above) Can be produced from compound (15) by reacting according to production method 1 or production method 3.
Further, the ester of compound (12) is hydrolyzed by a method known per se to obtain compound (16), and then reacted according to production method 1 and production method 3, whereby Z is * -CONHSO ₂ -** or *- CONNHSO ₂ N (R ² )-** (wherein R ² , * and ** are as defined above) is obtained as compound (17), and compound (17) is obtained from compound (12). It can manufacture by making it react according to the method of obtaining a compound (14).
Compound (11) and compound (13) used in this production method can be obtained as commercially available products, or can be produced according to a method known per se or a method analogous thereto.

(Manufacturing method 8)
(Production method 8-A)

[Wherein, A, B, R ³ , m and n are as defined above, and L ⁴ is hydroxy, halogen atom (for example, fluorine atom, chlorine atom, bromine atom, iodine atom), imidazolyl, succinimide] A leaving group such as oxy, alkanesulfonyloxy (eg, methanesulfonyloxy, ethanesulfonyloxy, propanesulfonyloxy, trifluoromethanesulfonyloxy, etc.) or arylsulfonyloxy (eg, benzenesulfonyloxy, tolylsulfonyloxy, etc.) is shown. ]

In production method 8-A, X of the compound (1) is * — (CH ₂ ) _m —O— (CH ₂ ) _n — ** (wherein m, n, * and ** are as defined above). This is a method for producing the compound (25).
Compound (25) can be produced by reacting compound (22) with compound (23) to obtain compound (24), and hydrolyzing the ester of compound (24) by a method known per se. it can.
In production method 8-A, when L ⁴ is hydroxy, the reaction between compound (22) and compound (23) is Mitsunobu reaction (“Reagents for Organic Synthesis” by Fieser & Fieser, Vol. 6, 645), etc. It is carried out by subjecting to a dehydration reaction as exemplified. The reaction is usually carried out by using azo compounds and phosphines in the presence of a solvent. Examples of the azo compounds include diC _1-6 alkyl azodicarboxylate (eg, dimethyl azodicarboxylate, diethyl azodicarboxylate, diisopropyl azodicarboxylate), azodicarboxamide (eg, 1,1′-azobis (N , N′-dimethylformamide, 1,1 ′-(azodicarbonyl) dipiperidine, etc.) Examples of phosphines include triarylphosphine (for example, triphenylphosphine), triC _1-8 alkylphosphine ( For example, tri-n-butylphosphine, tri-n-hexylphosphine, tri-n-octylphosphine, etc.) are used, and the solvent used in the reaction is not particularly limited as long as it does not inhibit the reaction. E.g. dioxane, acetonitrile, teto Hydrofuran, chloroform, methylene chloride, ethylene chloride, benzene, toluene, xylene, N, N'-dimethylformamide, N, N'-dimethylacetamide, dimethyl sulfoxide, and mixtures thereof.

The amount of compound (23) used is not particularly limited, and is usually 1 to 5 mol, preferably 1 to 3 mol, relative to 1 mol of compound (22). The amounts of azo compounds and phosphines used are respectively The amount is generally 1 to 5 mol, preferably 1 to 3 mol, per 1 mol of compound (22).
Although the reaction conditions such as reaction temperature and reaction time vary depending on the reaction reagent and reaction solvent used, the reaction temperature is usually −30 to 50 ° C., and the reaction time is 30 minutes to 20 hours.
In Production Method 8-A, the reaction of compound (22) and compound (23) is carried out in the presence of a base in a solvent that does not affect the reaction when L ⁴ is a leaving group.
The base used in the reaction is not particularly limited, and alkali metal carbonates (for example, sodium carbonate, sodium hydrogen carbonate, potassium carbonate, potassium hydrogen carbonate, cesium carbonate, etc.), metal hydride compounds (for example, sodium hydride) , Potassium hydride, calcium hydride, etc.), inorganic bases such as silver oxide; and alkali metal alcoholates (eg, sodium methoxide, sodium ethoxide, potassium t-butoxide, etc.), amines (eg, triethylamine, diisopropylethylamine, etc.) ) Organic bases.

The amount of compound (23) to be used is not particularly limited, and is usually 1 to 5 mol, preferably 1 to 3 mol, per 1 mol of compound (22), and the amount of base used is compound (22) or (23) The amount is usually 1 to 5 mol, preferably 1 to 3 mol, relative to 1 mol.
In this reaction, a catalyst can also be used in a solvent in the presence of a base. Suitable solvents are toluene and benzene, and catalysts include, for example, quaternary ammonium salts such as tetramethylammonium bromide, tetraethylammonium bromide, tetrabutylammonium bromide, tetraethylammonium chloride, tetraethylammonium fluoride, benzyltrimethylammonium bromide; And tris [2- (2-methoxyethoxy) ethyl] amine. Preferred is tetraethylammonium fluoride or tris [2- (2-methoxyethoxy) ethyl] amine. The amount of the catalyst to be used is generally 0.1-1 mol, preferably 0.1-0.5 mol, per 1 mol of compound (22).
Reaction conditions such as reaction temperature and reaction time vary depending on the reaction reagent and reaction solvent used, but the reaction temperature is usually from −30 to 150 ° C., and the reaction time is from 30 minutes to 20 hours.
Compound (22) and compound (23) used in this production method can be obtained as commercially available products, or can be produced according to a method known per se or a method analogous thereto.

(Production method 8-B)

[Wherein, A, B, R ³ , L ⁴ , m and n are as defined above]. ]

Production Method 8-B is a method for producing compound (25).
Compound (25) can be produced by reacting compound (26) and compound (27) to obtain compound (24), and hydrolyzing the ester of compound (24) by a method known per se. it can.
This production method is carried out by subjecting to the same reaction as described in Production Method 8-A.
Compound (26) and compound (27) used in this production method can be obtained as commercially available products, or can be produced according to a method known per se or a method analogous thereto.

(Production method 8-C)

[Wherein, A, B and R ³ are as defined above, and D represents a substituted boron atom or a compound (19) when the compound (19) is an organic boronic acid or an organic boronic acid ester. When is an organotin reagent, it represents a substituted tin atom. ]

Examples of the substituted boron atom represented by D include dihydroxyboryl, 4,4,5,5-tetramethyl-1,2,3-dioxaborolan-2-yl and the like. Examples of the substituted tin atom represented by D include trimethyltin and tributyltin.

Production method 8-C is a method for producing compound (30) in which X of compound (1) is —O—.
Compound (30) is obtained by subjecting compound (28) and compound (19) to a coupling reaction using an organometallic catalyst to obtain compound (29) by a method known per se. It can be produced by hydrolyzing the ester.
This production method is carried out in a solvent that does not affect the reaction, if necessary, in the presence of a base. Moreover, you may perform this manufacturing method in presence of a phosphine ligand as needed.
Examples of the organometallic catalyst include palladium (II) acetate, tetrakis (triphenylphosphine) palladium (0), tris (dibenzylideneacetone) dipalladium (0), dichlorobis (triphenylphosphine) palladium (II), and the like.

Examples of the base include alkali metal carbonates such as sodium carbonate, sodium hydrogen carbonate, potassium carbonate, potassium hydrogen carbonate and cesium carbonate; metal hydrides such as potassium hydride and sodium hydride.
Specific examples of solvents that do not adversely influence the reaction include acetone, dioxane, acetonitrile, benzene, toluene, xylene, hexane, heptane, diethyl ether, diisopropyl ether, tetrahydrofuran, dioxane, N, N′-dimethylformamide, N— Examples include methyl pyrrolidone, dimethyl sulfoxide, methanol, ethanol, tert-butyl alcohol, water, and mixtures thereof.

The amount of compound (19) to be used is generally 1 to 5 mol, preferably 1 to 3 mol, per 1 mol of compound (28).
The amount of the organometallic catalyst to be used is generally 0.001 to 1 mol, preferably 0.01 to 0.5 mol, per 1 mol of compound (28).
The amount of the base to be used is generally 1 to 10 mol, preferably 1 to 5 mol, per 1 mol of compound (28).
Examples of the phosphine ligand include 2,2′-bis (diphenylphosphino) -1,1′-binaphthyl (BINAP), tris (2-methylphenyl) phosphine, 1,1′-bis (diphenylphosphino) ferrocene, -Dicyclohexylphosphino-2 ', 6'-dimethoxybiphenyl and the like.
The amount of the phosphine ligand to be used is generally 0.001-1 mol, preferably 0.01-0.5 mol, per 1 mol of compound (28).
Reaction conditions such as reaction temperature and reaction time vary depending on the reaction reagent and reaction solvent used, but the reaction temperature is usually from −30 to 150 ° C., and the reaction time is from 30 minutes to 20 hours.
Compound (19) and compound (28) used in this production method can be obtained as commercially available products, or can be produced according to a method known per se or a method analogous thereto.

By reacting according to the production method 8, X is * — (CH ₂ ) _m —O— (CH ₂ ) _n — ** (wherein m, n, * and ** are as defined above). (1), (3), (6) and (9) are produced. Further, a compound in which X is * — (CH ₂ ) _m —O— (CH ₂ ) _n — ** (wherein m, n, * and ** are as defined above). 1), Compound (3), Compound (6), and Compound (9) are used in the same reaction as in Production Methods 1 to 6, whereby X is * — (CH ₂ ) _m —O— (CH ₂ ). Compound (Ia), Compound (Ib), Compound (Ic), Compound which is _n -** (wherein m, n, * and ** are as defined above) (Id), Compound (Ie), Compound (If) and Compound (Ig) can be produced.

(Manufacturing method 9)
(Production method 9-A)

[Wherein, A, B, R ³ , L ⁴ , m and n are as defined above]. ]

In production method 9-A, X of compound (1) is * — (CH ₂ ) _m —S— (CH ₂ ) _n — ** (wherein * and ** are as defined above). This is a method for producing a certain compound (33).
Compound (33) can be produced by reacting compound (31) with compound (27) to obtain compound (32), and hydrolyzing the ester of compound (32) by a method known per se. it can.
This production method is carried out by subjecting to the same reaction as described in Production Method 8-A.
Compound (27) and compound (31) used in this production method can be obtained as commercially available products, or can be produced according to a method known per se or a method analogous thereto.

(Production method 9-B)

[Wherein, A, B, R ³ , L ⁴ , m, n and p are as defined above. ]

Production Method 9-B is a method for producing compound (33) as in Production Method 9-A.
This production method is carried out by subjecting to the same reaction as described in the production method 9-A. Further, X of the compound (1) is * — (CH ₂ ) _m —S (O) _p — (CH ₂ ) _n — ** (wherein m, n, p, * and ** are the same as above) The compound (36) which is significant) can be produced by oxidizing the compound (32) by a method known per se to obtain the compound (35) and hydrolyzing the ester of the compound (35). it can.
Compound (22) and compound (34) used in this production method can be obtained as commercially available products, or can be produced according to a method known per se or a method analogous thereto.
By reacting according to production method 9, X is * — (CH ₂ ) _m —S (O) _p — (CH ₂ ) _n — ** (where m, n, p, * and ** are The compounds (1), (3), (6) and (9) are produced. Further, these X are * — (CH ₂ ) _m —S (O) _p — (CH ₂ ) _n — ** (wherein m, n, p, * and ** are as defined above). The compound (1), the compound (3), the compound (6) and the compound (9), which are the same as those in the production methods 1 to 6, are subjected to the reaction of X = * — (CH ₂ ) _m —. Compound (Ia), Compound (I) which is S (O) _p — (CH ₂ ) _n — ** (wherein m, n, p, * and ** are as defined above). -B), compound (Ic), compound (Id), compound (Ie), compound (If) and compound (Ig) can be produced.

(Manufacturing method 10)

[Wherein, A, B and R ³ are as defined above, and Q represents a halogen atom (for example, a fluorine atom, a chlorine atom, a bromine atom or an iodine atom). ]

Production method 10 is a method for producing compound (41) in which X of compound (1) is methylene and compound (43) in which X is —CO—.
Compound (39) is produced by lithiation of compound (38) with n-butyllithium or the like and reaction with compound (37).
Compound (40) is produced by reacting compound (39) with triethylsilane, and compound (41) is produced by hydrolyzing the obtained ester of compound (40) by a method known per se. The
Compound (43) is produced by oxidizing the hydroxy group of compound (39) by a method known per se and hydrolyzing the ester of compound (42) obtained by a method known per se.
Compound (37) and compound (38) used in this production method can be obtained as commercially available products, or can be produced according to a method known per se or a method analogous thereto.

By reacting according to production method 10, compound (1), compound (3), compound (6) and compound (9) wherein X is methylene, or compound (1), compound (3) wherein X is —CO—, Compound (6) and compound (9) are produced. Further, by using the compound (1), the compound (3), the compound (6), and the compound (9) in which X is methylene or X is —CO—, the same reaction as in production methods 1 to 6 is performed. , X is methylene or X is —CO—, compound (Ia), compound (Ib), compound (Ic), compound (Id), compound (Ie), compound (I -F) and compound (Ig) can be prepared.

(Manufacturing method 11)

[Wherein, A, B and R ³ are as defined above. ]

Production method 11 is a method for producing compound (47) in which X of compound (1) is vinylene and compound (48) in which X is ethylene.
Compound (47) is produced by subjecting compound (37) and an organic phosphorus reagent such as compound (44) to a carbon increase reaction to produce compound (45). The ester can be produced by hydrolysis by a method known per se. Compound (48) is produced by subjecting compound (45) to a hydrogenation reaction to produce compound (46), and hydrolyzing the resulting ester of compound (46) by a method known per se. Can be manufactured.
The carbon increase reaction for obtaining the compound (45) is carried out in the presence of a base in a solvent that does not affect the reaction.
Examples of the base used in the reaction include alkali metal carbonates such as sodium carbonate, sodium hydrogen carbonate, potassium carbonate, potassium hydrogen carbonate, and cesium carbonate; metal hydrides such as potassium hydride and sodium hydride. .

Specific solvents that do not adversely influence the reaction include acetone, dioxane, acetonitrile, benzene, toluene, xylene, hexane, heptane, chloroform, dichloromethane, diethyl ether, diisopropyl ether, tetrahydrofuran, dioxane, N, N′-dimethyl. Examples include formamide, N-methylpyrrolidone, dimethyl sulfoxide, methanol, ethanol, tert-butyl alcohol, water, and mixtures thereof.
The amount of compound (44) to be used is generally 1 to 5 mol, preferably 1 to 3 mol, per 1 mol of compound (37).
The amount of the base to be used is generally 1 to 10 mol, preferably 1 to 5 mol, per 1 mol of compound (37).
Reaction conditions such as reaction temperature and reaction time vary depending on the reaction reagent and reaction solvent used, but the reaction temperature is usually from −30 to 150 ° C., and the reaction time is from 30 minutes to 20 hours.
The hydrogenation reaction to obtain the compound (46) is hydrogenated using a metal catalyst such as palladium-carbon, palladium black, palladium chloride, platinum oxide, platinum black, Raney nickel in a solvent that does not affect the reaction. Is done.
Compound (37) and compound (44) used in this production method can be obtained as commercially available products, or can be produced according to a method known per se or a method analogous thereto.

By reacting according to production method 11, compound (1), compound (3), compound (6) and compound (9) wherein X is vinylene or compound (1), compound (3), compound (where X is ethylene) 6) and compound (9) are produced. Further, by using the compound (1), the compound (3), the compound (6) and the compound (9) in which X is vinylene or X is ethylene, the same reaction as in production methods 1 to 6 is carried out to give X Compound (Ia), Compound (Ib), Compound (Ic), Compound (Id), Compound (Ie), Compound (If), wherein is vinylene or X is ethylene and Compound (Ig) can be produced.

(Manufacturing method 12)

[Wherein, A, B, R ³ and Q are as defined above. ]

Production method 12 is a method for producing compound (51) in which X of compound (1) is ethynylene.
Compound (51) is obtained by subjecting Compound (18) and Compound (49) to a coupling reaction using an organometallic catalyst to obtain Compound (50) by a method known per se. It can be produced by hydrolyzing the ester.
This production method is carried out by subjecting to the same reaction as described in Production Method 8-C.
Compound (18) and compound (49) used in this production method can be obtained as commercially available products, or can be produced according to a method known per se or a method analogous thereto.
By reacting according to production method 12, compound (1), compound (3), compound (6) and compound (9), wherein X is ethynylene, are produced. Further, by using the compound (1), the compound (3), the compound (6) and the compound (9) in which X is ethynylene, X is ethynylene by subjecting to the same reaction as in Production Methods 1 to 6. Compound (Ia), Compound (Ib), Compound (Ic), Compound (Id), Compound (Ie), Compound (If), and Compound (Ig) are produced. can do.

(Manufacturing method 13)
(Production method 13-A)

[Wherein, A, X, R ³ and L ⁴ are as defined above, and B is a nitrogen-containing heterocyclic group. ]

Production method 13-A is a method for producing a compound (55) in which X is bonded to a nitrogen atom in B.

(Production method 13-B)

[Wherein, B, X, R ³ and L ⁴ are as defined above, and A is a nitrogen-containing heterocyclic group. ]

Production Method 13-B is a method for producing a compound (59) in which X is bonded to a nitrogen atom in A.
Production method 13 is carried out by subjecting the reaction to the same reaction as described in production method 8.
By reacting according to production method 13, compound (1), compound (3), compound (6) and compound (9) in which X is bound to the nitrogen atom in A or the nitrogen atom in B are produced. Further, using the compound (1), the compound (3), the compound (6) and the compound (9) in which these Xs are bonded to the nitrogen atom in A or the nitrogen atom in B, the same method as in Production methods 1 to 6 Compound (Ia), Compound (Ib), Compound (Ic), Compound (Id) in which X is bonded to the nitrogen atom in A or the nitrogen atom in B by subjecting to reaction. Compound (Ie), compound (If) and compound (Ig) can be produced.

(Manufacturing method 14)

[Wherein, A, B, C and X are as defined above. ]

Production method 14 is a method for producing a compound (Ii) in which, in the general formula (I), Z is * -CONCONHSO ₂ -** (wherein * and ** are as defined above). is there.
Compound (Ii) can be produced by subjecting compound (60) and compound (2) to a reaction similar to the amidation reaction described in Production Method 1.
The compound (60) used in this production method can be produced according to the following method.

[Wherein, A, B, X and Q are as defined above. ]

Compound (60) is obtained by lithiation with alkyllithium such as n-BuLi in a solvent that does not affect the reaction of compound (61), and then reacted with diethyl oxalate to obtain compound (62), which is known per se This can be produced by hydrolyzing the ester of compound (62).
Compound (61) used in this production method can be obtained as a commercially available product, or can be produced according to a method known per se or a method analogous thereto.

(Manufacturing method 15)

[Wherein, A, B, C and X are as defined above. ]

Production method 15 is a method for producing compound (Ij) in which, in general formula (I), Z is * —SO ₂ NHCOCO-** (wherein * and ** are as defined above). It is.
Compound (Ij) can be produced by subjecting compound (3) and compound (63) to a reaction similar to the amidation reaction described in Production Method 1.
Compound (3) and compound (63) used in this production method can be obtained as commercially available products, or can be produced according to a method known per se or a method analogous thereto.

(Manufacturing method 16)

[Wherein, A, B, C, X and R ² are as defined above. ]

In the production method 16, in general formula (I), Z is * —N (R ² ) COCONHSO ₂ — ** (wherein R ² , * and ** are as defined above). -K).
Compound (Ik) can be produced by subjecting compound (64) and compound (2) to a reaction similar to the amidation reaction described in Production Method 1.
Compound (64) used in this production method can be produced according to the following method.

[Wherein, A, B, X and R ² are as defined above. ]

Compound (64) is a method known per se by reacting compound (6) with ethyl chloroglyoxylate in the presence of a base such as triethylamine in a solvent that does not affect the reaction, to give compound (65). Thus, the ester of compound (65) can be hydrolyzed.
Compound (6) used in this production method can be obtained as a commercial product, or can be produced according to a method known per se or a method analogous thereto.

(Manufacturing method 17)

[Wherein, A, B, C, X and R ² are as defined above. ]

In the production method 17, in general formula (I), Z is * -SO ₂ NHCOCON (R ² )-** (wherein R ² , * and ** are as defined above). -L).
Compound (Il) can be produced by subjecting compound (3) and compound (66) to a reaction similar to the amidation reaction described in Production Method 1.
Compound (3) and compound (66) used in this production method can be obtained as commercially available products, or can be produced according to a method known per se or a method analogous thereto.

(Manufacturing method 18)

[Wherein, A, B, C and X are as defined above, and M represents an alkali metal such as sodium or potassium. ]

Production method 18 is a method for producing compound (1-ab) which is an alkali metal salt from compound (1-a).
Compound (1-ab) can be produced by reacting compound (1-a) with a base.
Examples of the base used in the reaction include alkali metal carbonates such as sodium carbonate, sodium hydrogen carbonate, potassium carbonate, and potassium hydrogen carbonate; metal hydrides such as potassium hydride and sodium hydride, and alcoholates such as sodium methoxide. Etc.

Specific examples of solvents that do not affect the reaction include acetone, acetonitrile, diethyl ether, diisopropyl ether, tetrahydrofuran, dioxane, N, N′-dimethylformamide, dimethyl sulfoxide, methanol, ethanol, tert-butyl alcohol, water, Examples thereof include a mixture thereof.
The amount of the base to be used is generally 1 to 5 mol, preferably 1 to 2 mol, per 1 mol of compound (1-a).
Reaction conditions such as reaction temperature and reaction time vary depending on the reaction reagent and reaction solvent used, but the reaction temperature is usually from −30 to 150 ° C., and the reaction time is from 30 minutes to 20 hours.
By reacting in the same manner according to production method 18, compounds (Ib), (Ic), (Id), (Ie), (If), (Ig), (I The corresponding alkali metal salts can be prepared from -h), (Ii), (Ij), (Ik) and (Il).

Compound (I) obtained by the above production method 1-18 can be isolated by a conventional method, and if necessary, purified by a conventional method such as recrystallization, preparative thin layer chromatography, column chromatography, etc. can do.

When the compound (I) contains an optical isomer, a stereoisomer, a positional isomer, and a rotational isomer, these are also contained as the compound (I).

Compound (I) of the present invention can be converted to a pharmaceutically acceptable salt thereof by a method known per se.

The pharmaceutical composition containing the compound (I) of the present invention or a pharmaceutically acceptable salt thereof can be formulated with a pharmaceutically acceptable carrier. Examples of the carrier include excipients (eg, starch, lactose, sugar, calcium carbonate, calcium phosphate, etc.), binders (eg, starch, gum arabic, carboxymethylcellulose, hydroxypropylcellulose, crystalline cellulose, etc.), lubricants (For example, magnesium stearate, talc, etc.), disintegrating agents (for example, carboxymethyl cellulose, talc, etc.) and the like can be mentioned.
After mixing the above-mentioned components, the mixture is subjected to per se known means, for example, for oral administration such as capsules, tablets, fine granules, granules, dry syrups, or for parenteral administration such as injections and suppositories. It can be a formulation.

The dose of the compound (I) of the present invention or a pharmaceutically acceptable salt thereof varies depending on the administration subject, symptoms, and other factors. For example, for patients with diabetes, diabetic complications or hyperlipidemia, When orally administered to adults, give 1 to 500 mg at a time, about 1 to 3 times daily.

The compound (I) of the present invention or a pharmaceutically acceptable salt thereof has protein tyrosine phosphatase-1B (PTP-1B; ProteinＰｒｏTyrosine Phosphatase-1B) inhibitory activity, and is a mammal (human, horse, cow, dog, Cats, rats, mice, hamsters, etc.) have excellent blood glucose lowering effect, blood lipid lowering effect, insulin resistance improving action, antihyperglycemic agent, antihyperlipidemic agent, insulin resistance improving agent , Antidiabetic agent, diabetic complication agent, glucose intolerance improving agent, anti-arteriosclerosis agent, anti-obesity agent, anti-inflammatory agent, prevention / treatment agent of PTP-1B-mediated diseases and prevention / metabolic syndrome It is useful as a therapeutic agent. That is, the compound (I) of the present invention or a pharmaceutically acceptable salt thereof contains hyperglycemia, hyperlipidemia, diabetes, diabetic complications, diseases caused by insulin resistance, diseases caused by impaired glucose tolerance, It is useful as a prophylactic and therapeutic agent for arteriosclerosis, obesity, inflammation, diseases mediated by PTP-1B and metabolic syndrome.

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

Example 1
(E) -N- [4- (1-Ethyl-2,3-dihydro-1H-indole-5-ylmethyleneaminooxy) benzoyl] -5-chlorothiophene-2-sulfonamide

(1) 2,3-Dihydro-1H-indole (7.0 g) was dissolved in N, N'-dimethylformamide (DMF) (60 mL), and sodium hydride (60%) (2.58 g) was added under ice cooling. After stirring for 30 minutes, ethyl iodide (6.1 mL) was added, and the mixture was stirred at the same temperature for 7.5 hours. The mixture was poured into ice water (100 mL) and extracted twice with ethyl acetate (AcOEt) (100 mL). The organic layers were combined, washed successively with water and saturated brine, and dried (Na ₂ SO ₄ ). The solvent was distilled off under reduced pressure to obtain a brown oily substance (10.6 g) of 1-ethyl-2,3-dihydro-1H-indole.

(2) Under ice-cooling, phosphorus oxychloride (16.4 mL) was added to DMF (22 mL), and after stirring for 1 hour, a solution of the compound obtained in (1) (10.6 g) in DMF (22 mL) was added. Stir at 50 ° C. for 1 hour. The reaction mixture was added to ice water (200 mL) in which sodium hydroxide (23 g) was dissolved, neutralized with sodium bicarbonate, and extracted twice with AcOEt (100 mL). The organic layers were combined, washed successively with saturated aqueous sodium hydrogen carbonate, water and saturated brine, dried (Na ₂ SO ₄ ), and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography, and the solvent of the target fraction was distilled off under reduced pressure to give 1-ethyl-2,3-dihydro-1H-indole-5-carbaldehyde as a yellow oil (5.96 g). It was.
¹ H-NMR (CDCl ₃ , 400 MHz) δ (ppm); 1.20 (3H, t, J = 7.2 Hz), 3.04 (2H, t, J = 8.5 Hz), 3.29 (2H, t, J = 7.2 Hz) ), 3.59 (2H, t, J = 8.5 Hz), 6.37 (1H, d, J = 8.5 Hz), 7.52-7.57 (2H, m), 9.65 (1H, s).

(3) Ethyl N-hydroxyacetimidate (12.3 g) was dissolved in DMF (120 mL), potassium tert-butoxide (13.4 g) was added, and the mixture was stirred for 50 minutes, and then ethyl 4-fluorobenzoate ( 10.0 g) was added, and the mixture was stirred at the same temperature for 30 minutes and then at room temperature for 16 hours. The mixture was poured into ice water (200 mL) and extracted twice with AcOEt (100 mL). The organic layers were combined, washed successively with water and saturated brine, dried (Na ₂ SO ₄ ), and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography, and the solvent of the target fraction was distilled off under reduced pressure to obtain a white powder (8.82 g) of ethyl 4- (1-ethoxyethylideneaminooxy) benzoate.
¹ H-NMR (CDCl ₃ , 400 MHz) δ (ppm); 1.37 (6H, q, J = 7.1 Hz), 2.13 (3H, s), 4.21 (2H, q, J = 7.1 Hz), 4.34 (2H , q, J = 7.1 Hz), 7.13-7.18 (2H, m), 7.95-8.00 (2H, m).

(4) The compound (3.00 g) obtained in (2) and the compound (4.30 g) obtained in (3) were dissolved in 1,4-dioxane (34 mL), and HClO ₄ (60 %) (1.6 mL) was added, and the mixture was stirred at room temperature for 3.5 hours. Water (50 mL) and saturated aqueous sodium hydrogen carbonate (20 mL) were added, and the mixture was extracted 3 times with AcOEt (50 mL). The organic layers were combined, washed successively with saturated aqueous sodium hydrogen carbonate and saturated brine, dried (Na ₂ SO ₄ ), and the solvent was evaporated under reduced pressure. After the residue was purified by column chromatography, the solvent of the target fraction was distilled off under reduced pressure to obtain ethyl (E) -4- (1-ethyl-2,3-dihydro-1H-indol-5-ylmethyleneaminooxy ) A yellow oil (4.0 g) of benzoate was obtained.
¹ H-NMR (CDCl ₃ , 400 MHz) δ (ppm); 1.19 (3H, t, J = 7.2 Hz), 1.39 (3H, t, J = 7.1 Hz), 3.02 (2H, t, J = 8.4 Hz) ), 3.22 (2H, q, J = 7.1 Hz), 3.49 (2H, t, J = 8.4 Hz), 4.35 (2H, q, J = 7.2 Hz), 6.39 (1H, d, J = 8.1 Hz), 7.23-7.28 (2H, m), 7.29 (1H, dd, J = 8.1, 1.7 Hz), 7.52 (1H, d, J = 1.7 Hz), 7.98-8.03 (2H, m), 8.29 (1H, s, -CHO).

(5) The compound (4.0 g) obtained in (4) was dissolved in methanol (MeOH) -tetrahydrofuran (THF) (1: 3) (80 mL), and 1.0 M LiOH aqueous solution (36 mL) was added. Stir at 0 ° C. for 1 hour. After adjusting pH <4 with 10% aqueous citric acid solution, the mixture was extracted with AcOEt, washed successively with water and saturated brine, dried (Na ₂ SO ₄ ), and the solvent was evaporated under reduced pressure. Diisopropyl ether (i-Pr ₂ O) (80 mL) was added to the residue, and after stirring for 15 minutes, the precipitate was collected by filtration to give (E) -4- (1-ethyl-2,3-dihydro-1H-indole An orange powder (2.3 g) of -5-ylmethyleneaminooxy) benzoic acid was obtained.
IRν (ATR) cm ^-1 ; 1674
¹ H-NMR (CDCl ₃ , 400 MHz) δ (ppm); 1.20 (3H, t, J = 7.1 Hz), 3.03 (2H, t, J = 8.3 Hz), 3.23 (2H, q, J = 7.1 Hz ), 3.49 (2H, t, J = 8.3 Hz), 6.40 (1H, d, J = 8.3 Hz), 7.27-7.32 (2H, m), 7.51-7.54 (1H, m), 8.05-8.10 (2H, m), 8.30 (1H, s).

(6) Dissolve the compound (200 mg) obtained in (5) in DMF (2 mL), add carbonyldiimidazole (CDI) (125 mg) at room temperature, stir for 30 minutes, and then 5-chlorothiophene. -2-sulfonamide (152 mg) and 1,8-diazabicyclo [5.4.0] -7-undecene (DBU) (0.12 mL) were added and stirred for 14 hours. Water was added and the mixture was extracted twice with AcOEt. The organic layers were combined, washed successively with water, 10% aqueous citric acid solution and saturated brine, and dried (Na ₂ SO ₄ ). The solvent was evaporated under reduced pressure, and i-Pr ₂ O (8 mL) was added to the residue. After washing, the residue was collected by filtration to give the title compound as a yellow powder (149 mg).
IRν (ATR) cm ^-1 ; 1597
¹ H-NMR (CDCl ₃ , 400 MHz) δ (ppm); 0.88 (3H, t, J = 7.3 Hz), 2.97 (2H, t, J = 8.4 Hz), 3.21 (2H, q, J = 7.3 Hz) ), 3.45 (2H, t, J = 8.4 Hz), 6.48 (1H, d, J = 8.0 Hz), 7.10 (1H, d, J = 3.9 Hz), 7.18 (2H, m), 7.34 (1H, d , J = 8.0 Hz), 7.46-7.51 (2H, m), 8.46 (1H, s).

Example 2
(E) -N- [4- (1-Acetyl-2,3-dihydro-1H-indol-5-ylmethyleneaminooxy) benzoyl] -2,4-dichlorobenzenesulfonamide

(1) Dissolve ethyl N-hydroxyacetimidate (100 g) in DMF (3.3 L), add potassium tert-butoxide (103.2 g) under ice-cooling, and stir for 50 minutes. -A solution of fluorobenzoate (71.2 g) in DMF (100 mL) was added dropwise, and the mixture was stirred at room temperature for 3 hours. The mixture was poured into ice water (6 L) and extracted with AcOEt (2 L). The organic layer was washed successively with water and saturated brine, dried (Na ₂ SO ₄ ), and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography, and then the solvent of the target fraction was distilled off under reduced pressure to obtain white powder (86.4 g) of methyl 4- (1-ethoxyethylideneaminooxy) benzoate.

(2) Dissolve the compound (86.4 g) obtained in (1) in MeOH-THF (1: 3) (860 mL), add 4.4 M LiOH aqueous solution (230 mL), and stir at 40 ° C. for 6 hours. did. Adjust to pH <3 with 10% aqueous citric acid solution, extract with AcOEt (1 L), wash sequentially with water and saturated brine, dry (Na ₂ SO ₄ ), and evaporate the solvent under reduced pressure. did. N-Hexane was added to the residue, and the precipitate was collected by filtration to give white powder (65.3 g) of 4- (1-ethoxyethylideneaminooxy) benzoic acid.

(3) The compound (5.58 g) obtained in (2) was dissolved in DMF (56 mL), CDI (4.72 g) was added at room temperature, stirred for 1 hour, and 2,4-dichlorobenzenesulfonamide ( 6.22 g) and DBU (4.1 mL) were added, and the mixture was stirred at the same temperature for 14 hours. A 10% aqueous citric acid solution (100 mL) was added, and the mixture was extracted with AcOEt (100 mL). The organic layer was washed with saturated brine, dried (Na ₂ SO ₄ ), and the solvent was evaporated under reduced pressure. The residue was dissolved in AcOEt (80 mL) with heating, n-hexane (550 mL) was added, and the mixture was stirred at room temperature for 1 hr. The precipitated crystals were collected by filtration to obtain a slightly yellow powder (8.6 g) of ethyl N- [4- (2,4-dichlorobenzenesulfonylaminocarbonyl) phenoxy] acetamide.

(4) Dissolve the compound (250 mg) obtained in (3) and 1-acetyl-2,3-dihydro-1H-indole-5-carbaldehyde (110 mg) in 1,4-dioxane (11 mL) Ice-cooled HClO ₄ (60%) (0.09 mL) was added, and the mixture was stirred at room temperature for 14 hours. Water (50 mL) and AcOEt (30 mL) were added, the two layers were separated, and the aqueous layer was extracted twice with AcOEt. The organic layers were combined, washed successively with water (200 mL) and saturated brine, dried (Na ₂ SO ₄ ), and the solvent was evaporated under reduced pressure. The resulting yellow powder was purified by column chromatography. The obtained crude product was dissolved in AcOEt (10 mL) with heating, diethyl ether (Et ₂ O) (40 mL) was added, and the mixture was stirred at room temperature for 4 hours. The precipitate was collected by filtration to give a pink powder (242 mg) of the title compound.
IRν (ATR) cm ^-1 ; 1645, 1597
¹ H-NMR (CDCl ₃ , 400 MHz) δ (ppm); 2.26 (3H, s), 3.24 (2H, t, J = 8.6 Hz), 4.11 (2H, t, J = 8.6 Hz), 7.28 (2H , m), 7.42 (1H, d, J = 8.3 Hz), 7.48 (1H, dd, J = 8.5 Hz, 1.7 Hz), 7.51 (1H, d, J = 1.7 Hz), 7.62 (1H, s), 7.83 (2H, m), 8.22 (1H, d, J = 8.3 Hz), 8.31 (1H, d, J = 8.5 Hz), 8.33 (1H, s), 9.37-9.65 (1H, br).

Example 3
2,4-dichloro-N- {4- [1- (1-ethyl-2,3-dihydro-1H-indol-5-yl) ethylideneaminooxy] benzoyl} benzenesulfonamide

(1) Indole-5-carboxylic acid (1.05 g) was dissolved in CH ₂ Cl ₂ (11 mL), and O, N-dimethylhydroxyamine (699 mg) and 1-ethyl-3- (3 -Dimethylaminopropyl) carbodiimide (EDC) (1.62 g) was added, then triethylamine (Et ₃ N) (1.09 mL) was added dropwise, and the mixture was stirred at room temperature for 3 hours. The reaction mixture was washed successively with 10% aqueous citric acid solution (20 mL) and saturated brine, and dried (Na ₂ SO ₄ ). The solvent was distilled off under reduced pressure to obtain a white powder (1.33 g) of indole-5-carboxylic acid methoxymethylamide.
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 3.26 (3H, s), 3.55 (3H, s), 6.47-6.55 (1H, m), 7.35-7.45 (3H, m), 7.89 (1H, s), 11.21-11.42 (1H, br).

(2) The compound (1.33 g) obtained in (1) was dissolved in acetic acid (AcOH) (9.3 mL), and NaBH ₃ CN (2.05 g) was added under ice cooling, followed by stirring at the same temperature for 4 hours. Water (30 mL) was added to the reaction solution, neutralized with K ₂ CO ₃ , and extracted twice with AcOEt (20 mL). The organic layers were combined, washed with water (50 mL) and saturated brine, dried (Na ₂ SO ₄ ), and the solvent was evaporated under reduced pressure. The resulting residue was purified by column chromatography to obtain 2,3-dihydro-1H-indole-5-carboxylic acid methoxymethylamide yellow oil (1.34 g).
¹ H-NMR (CDCl ₃ , 400 MHz) δ (ppm); 2.94 (2H, t, J = 8.6 Hz), 3.18 (3H, s), 3.48 (2H, t, J = 8.6 Hz), 3.51 (3H , s), 5.98-6.12 (1H, br), 6.43 (1H, d, J = 8.0 Hz), 7.28-7.36 (2H, m).

(3) The compound (2.62 g) obtained in (2) is dissolved in DMF (26 mL), ethyl iodide (1.12 mL) and K ₂ CO ₃ (2.28 g) are added, and the mixture is stirred at room temperature for 4.5 hours. Stir at 40 ° C. for 1 hour. Water (60 mL) was added to the reaction mixture, and the mixture was extracted twice with AcOEt (30 mL). The organic layers were combined, washed successively with water and saturated brine, dried (Na ₂ SO ₄ ), and the solvent was evaporated under reduced pressure. The obtained residue was purified by column chromatography to obtain a yellow oil (430 mg) of 1-ethyl-2,3-dihydro-1H-indole-5-carboxylic acid methoxymethylamide.
¹ H-NMR (CDCl ₃ , 400 MHz) δ (ppm); 1.18 (3H, t, J = 7.1 Hz), 2.99 (2H, t, J = 8.3 Hz), 3.20 (3H, q, J = 7.1 Hz ), 3.33 (3H, s), 3.45 (2H, t, J = 8.3 Hz), 3.59 (3H, s), 6.36 (1H, d, J = 8.1 Hz), 7.48 (1H, d, J = 1.2 Hz) ), 7.55 (1H, dd, J = 8.1 Hz, 1.2 Hz).

(4) The compound (430 mg) obtained in (3) was dissolved in THF (4.3 mL), and 2.0 M methylmagnesium iodide-Et ₂ O (4.6 mL) was added dropwise under ice cooling in a nitrogen atmosphere. Then, the mixture was stirred at room temperature for 72.5 hours. Under ice cooling, water (10 mL) was added dropwise to the reaction mixture, and the mixture was extracted 3 times with AcOEt (20 mL). The organic layers were combined, washed successively with water and saturated brine, dried (Na ₂ SO ₄ ), and the solvent was evaporated under reduced pressure. The obtained residue was purified by column chromatography to obtain a yellow oily substance (200 mg) of 5-acetyl-1-ethyl-2,3-dihydro-1H-indole.
¹ H-NMR (CDCl ₃ , 400 MHz) δ (ppm); 1.19 (3H, t, J = 7.1 Hz), 2.48 (3H, s), 3.01 (2H, t, J = 8.5 Hz), 3.25 (3H , q, J = 7.1 Hz), 3.53 (2H, t, J = 8.5 Hz), 6.33 (1H, d, J = 8.3 Hz), 7.67 (1H, d, J = 1.4 Hz), 7.73 (1H, dd , J = 8.3 Hz, 1.4 Hz).

(5) The compound (431 mg) obtained in Example 2 (3) and the compound (190 mg) obtained in (4) were dissolved in 1,4-dioxane (19 mL), and HClO was added under ice cooling. ₄ (60%) (0.16 mL) was added, and the mixture was stirred at room temperature for 15 hours. Water (40 mL) was added, and the mixture was extracted 3 times with AcOEt (30 mL). The organic layers were combined, washed successively with water and saturated brine, and dried (Na ₂ SO ₄ ). The solvent was distilled off under reduced pressure, and the resulting residue was purified by column chromatography. The obtained brown oil was dissolved in AcOEt (8 mL) with heating, Et ₂ O (30 mL) was added, and the mixture was stirred at room temperature for 1 hr, and the precipitate was collected by filtration. The obtained light brown powder (250 mg) was dissolved in AcOEt (3.5 mL) with heating, Et ₂ O (30 mL) and n-hexane (5 mL) were added, and the mixture was stirred for 1 hour under ice cooling. The precipitate was collected by filtration to give a pale brown powder (140 mg) of the title compound.
IRν (ATR) cm ^-1 ; 1691
¹ H-NMR (CDCl ₃ , 400 MHz) δ (ppm); 1.19 (3H, t, J = 7.1 Hz), 2.38 (3H, s), 3.01 (2H, t, J = 8.3 Hz), 3.21 (2H , q, J = 7.1 Hz), 3.45 (2H, t, J = 8.3 Hz), 6.41 (1H, d, J = 8.0 Hz), 7.33 (2H, m), 7.41-7.59 (4H, m), 7.78 (2H, m), 8.31 (1H, d, J = 8.6 Hz), 8.83-9.32 (1H, br).

Example 4
(E) -2,4-Dichloro-N- [4- (2,3-dihydro-1H-indole-5-ylmethyleneaminooxy) benzoyl] benzenesulfonamide hydrochloride

(1) The compound (500 mg) obtained in Example 2 (3) and 1- (2,2,2-trifluoroacetyl) -2,3-dihydro-1H-indole-5-carbaldehyde (282 mg) ) Was dissolved in 1,4-dioxane (28 mL), HClO ₄ (0.19 mL) was added under ice cooling, and the mixture was stirred at room temperature for 14.5 hours. Water (60 mL) was added and extracted twice with AcOEt (30 mL). The organic layers were combined, washed successively with water and saturated brine, and dried (Na ₂ SO ₄ ). The solvent was distilled off under reduced pressure, and the resulting residue was purified by column chromatography, and (E) -2,4-dichloro-N- {4- [1- (2,2,2-trifluoroacetyl) A light brown foamy powder (540 mg) of -2,3-dihydro-1H-indole-5-ylmethyleneaminooxy] benzoyl} benzenesulfonamide was obtained.
¹ H-NMR (CDCl ₃ , 400 MHz) δ (ppm); 3.33 (2H, t, J = 8.3 Hz), 4.36 (2H, t, J = 8.3 Hz), 7.32 (2H, m), 7.45-7.59 (3H, m), 7.72 (1H, s), 7.80 (2H, m), 8.27 (1H, d, J = 8.3 Hz), 8.33 (1H, d, J = 8.5 Hz), 8.41 (1H, s) , 8.81-9.08 (1H, br).

(2) The compound (540 mg) obtained in (1) was dissolved in 1,4-dioxane (5.4 mL), 1.0 M aqueous LiOH solution (1.4 mL) was added, and the mixture was stirred at room temperature for 45 minutes, then 1.0 M LiOH aqueous solution (1.4 mL) was added, and the mixture was further stirred for 50 minutes. Water (20 mL) was added to the reaction mixture, and the mixture was extracted 5 times with AcOEt (20 mL). The organic layers were combined, washed successively with water and saturated brine, dried (Na ₂ SO ₄ ), and the solvent was evaporated under reduced pressure. The obtained residue was purified by column chromatography. The obtained residue was dissolved in a mixture of CHCl ₃ (10 mL) and MeOH (3 mL) with heating, and 8.6 M hydrogen chloride-isopropanol (IPA) (0.07 mL) was added under ice cooling, followed by stirring at the same temperature for 10 minutes. Thereafter, Et ₂ O (40 mL) was added, and the mixture was further stirred at the same temperature for 1 hour. The precipitate was collected by filtration to give the title compound as a brown powder (69 mg).
IRν (ATR) cm ^-1 ; 1687
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 3.09 (2H, t, J = 8.3 Hz), 3.62 (2H, t, J = 8.3 Hz), 3.95-5.40 (3H, m) , 6.92 (1H, d, J = 7.8 Hz), 7.32 (2H, m), 7.51 (1H, d, J = 7.8 Hz), 7.67 (1H, s), 7.73 (1H, dd, J = 8.5 Hz, 1.7 Hz), 7.90 (1H, d, J = 1.7 Hz), 7.96 (2H, m), 8.17 (1H, d, J = 8.5 Hz), 8.64 (1H, s).

The compounds of Examples 5 to 32 were produced in the same manner as in Examples 1 to 4.

Example 5
(E) -2,4-Dichloro-N- [4- (indan-5-ylmethyleneaminooxy) benzoyl] benzenesulfonamide
IRν (ATR) cm ^-1 ; 1691, 1598, 1571, 1506
¹ H-NMR (CDCl ₃ , 400 MHz) δ (ppm); 2.08-2.16 (2H, m), 2.95 (4H, t, J = 7.3 Hz), 7.28 (1H, d, J = 7.8 Hz), 7.30 (2H, m), 7.44 (1H, d, J = 7.8 Hz), 7.46-7.50 (1H, m), 7.52 (1H, d, J = 2.0 Hz), 7.61 (1H, s), 7.80 (2H, m), 8.32 (1H, d, J = 8.5 Hz), 8.40 (1H, s), 8.89-9.35 (1H, br).

Example 6
(E) -2,4-Dichloro-N- [4- (4-isopropylbenzylideneaminooxy) benzoyl] benzenesulfonamide
IRν (ATR) cm ^-1 ; 1678.
¹ H-NMR (CDCl ₃ , 400 MHz) δ (ppm); 1.27 (6H, d, J = 6.8 Hz), 2.90-3.03 (1H, m), 7.30 (2H, d, J = 8.0 Hz), 7.30 (2H, m), 7.49 (1H, dd, J = 8.6 Hz, 2.0 Hz), 7.52 (1H, d, J = 2.0 Hz), 7.64 (2H, d, J = 8.0 Hz), 7.81 (2H, m ), 8.32 (1H, d, J = 8.6 Hz), 8.40 (1H, s), 8.99-9.42 (1H, br).

Example 7
(E) -N- [4- (4-Ethylaminobenzylideneaminooxy) benzoyl] -2,4-dichlorobenzenesulfonamide hydrochloride
IRν (ATR) cm ^-1 ; 1597
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 1.20 (3H, t, J = 7.1 Hz), 3.15 (3H, t, J = 7.1 Hz), 4.75-6.00 (3H, br) , 6.79-6.98 (2H, br), 7.30 (2H, m), 7.62 (2H, m), 7.74 (1H, dd, J = 8.6, 2.0 Hz), 7.90 (1H, d, J = 2.0 Hz), 7.96 (2H, m), 8.17 (1H, d, J = 8.6 Hz), 8.58 (1H, s).

Example 8
2,4-Dichloro-N- [4- (indan-2-ylmethyleneaminooxy) benzoyl] benzenesulfonamide
IRν (ATR) cm ^-1 ; 1693
¹ H-NMR (CDCl ₃ , 400 MHz) δ (ppm); 3.00-3.13 (2H, m), 3.19-3.31 (2H, m), 3.40-3.52 (1H, m), 7.12-7.30 (6H, m ), 7.43-7.55 (2H, m), 7.68-7.80 (2H, m), 7.88 (1H, d, J = 6.8 Hz), 8.30 (1H, d, J = 8.5 Hz), 8.78-9.15 (1H, br).

Example 9
(E) -3,5-dichloro-N- [4- (1-ethyl-2,3-dihydro-1H-indol-5-ylmethyleneaminooxy) benzoyl] benzenesulfonamide
IRν (ATR) cm ^-1 ; 1709
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 1.10 (3H, t, J = 7.1 Hz), 2.96 (2H, t, J = 8.3 Hz), 3.21 (2H, q, J = 7.1 Hz), 3.45 (2H, t, J = 8.3 Hz), 6.49 (1H, d, J = 8.1 Hz), 7.24-7.31 (2H, m), 7.35 (1H, d, J = 8.1 Hz), 7.49 (1H, s), 7.87-7.95 (4H, m), 8.00-8.06 (1H, br), 8.50 (1H, s).

Example 10
(E) -N- [4- (1-Ethyl-2,3-dihydro-1H-indol-5-ylmethyleneaminooxy) benzoyl] -2,4-diisopropylbenzenesulfonamide
IRν (ATR) cm ^-1 ; 1687
¹ H-NMR (CDCl ₃ , 400 MHz) δ (ppm); 1.19 (3H, t), 1.25 (6H, d), 1.27 (6H, d, J = 6.8 Hz), 2.88-3.00 (1H, m) , 3.84-3.95 (1H, m), 3.01 (2H, t, J = 8.5 Hz), 3.22 (2H, q, J = 7.1 Hz), 3.49 (2H, t, J = 8.5 Hz), 6.38 (1H, d, J = 8.3 Hz), 7.22-7.32 (5H, m), 7.50 (1H, s), 7.75-7.81 (2H, m), 8.19 (1H, d, J = 8.3 Hz), 8.27 (1H, s ), 8.91 (1H, s).

Example 11
(E) -4-Bromo-2-chloro-N- [4- (1-ethyl-2,3-dihydro-1H-indol-5-ylmethyleneaminooxy) benzoyl] benzenesulfonamide
IRν (ATR) cm ^-1 ; 1687
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 1.09 (3H, t, J = 7.1 Hz), 2.95 (2H, t, J = 8.5 Hz), 3.20 (2H, q, J = 7.1 Hz), 3.45 (2H, t, J = 8.5 Hz), 6.49 (1H, d, J = 8.3 Hz), 7.25-7.30 (2H, m), 7.35 (1H, dd, J = 8.3 Hz, 1.2 Hz ), 7.49 (1H, d, J = 1.2 Hz), 7.84 (1H, dd, J = 8.3, 2.0 Hz), 7.90-7.95 (2H, m), 7.92-7.98 (2H, m), 8.00 (1H, d, J = 2.0 Hz), 8.07 (1H, d, J = 8.3 Hz), 8.50 (1H, s).

Example 12
(E) -2-Bromo-4-chloro-N- [4- (1-ethyl-2,3-dihydro-1H-indol-5-ylmethyleneaminooxy) benzoyl] benzenesulfonamide
IRν (ATR) cm ^-1 ; 1693
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 1.09 (3H, t, J = 7.3 Hz), 2.95 (2H, t, J = 8.5 Hz), 3.20 (2H, q, J = 7.3 Hz), 3.45 (2H, t, J = 8.5 Hz), 6.49 (1H, d, J = 8.0 Hz), 7.25-7.30 (2H, m), 7.35 (1H, dd, J = 8.0 Hz, 1.2 Hz ), 7.49 (1H, d, J = 1.2 Hz), 7.75 (1H, dd, J = 8.3, 2.0 Hz), 7.92-7.98 (2H, m), 8.02 (1H, d, J = 2.0 Hz), 8.18 (1H, d, J = 8.3 Hz), 8.51 (1H, s).

Example 13
(E) -N- [4- (1-Ethyl-2,3-dihydro-1H-indole-5-ylmethyleneaminooxy) benzoyl] -3-methoxybenzenesulfonamide
IRν (ATR) cm ^-1 ; 1687
¹ H-NMR (CDCl ₃ , 400 MHz) δ (ppm); 1.18 (3H, t, J = 7.3 Hz), 3.01 (2H, t, J = 8.3 Hz), 3.21 (2H, q, J = 7.3 Hz) ), 3.48 (2H, t, J = 8.3 Hz), 3.87 (3H, s), 6.37 (1H, d, J = 8.1 Hz), 7.15 (1H, dd, J = 8.0, 1.7 Hz), 7.22-7.33 (3H, m), 7.44 (1H, t, J = 8.0 Hz), 7.50 (1H, s), 7.65-7.74 (1H, m), 7.72 (1H, d, J = 8.0 Hz), 7.76-7.83 ( 2H, m), 8.26 (1H, s).

Example 14
N- [4- (1-Ethyl-2,3-dihydro-1H-indol-5-ylmethyleneaminooxy) benzoyl] -2,4-dimethylbenzenesulfonamide
IRν (ATR) cm ^-1 ; 1691, 1601
¹ H-NMR (CDCl ₃ , 400 MHz) δ (ppm); 1.19 (3H, t, J = 7.1 Hz), 2.38 (3H, s), 2.66 (3H, s), 3.02 (2H, t, J = 8.5 Hz), 3.22 (2H, q, J = 7.1 Hz), 3.49 (2H, t, J = 8.5 Hz), 6.38 (1H, t, J = 8.0 Hz), 7.10 (1H, s), 7.20 (1H , d, J = 8.3 Hz), 7.25-7.32 (3H, m), 7.47-7.53 (1H, m), 7.71-7.78 (2H, m), 8.15 (1H, d, J = 8.3 Hz), 8.27 ( 1H, s), 8.67-8.80 (1H, br).

Example 15
(E) -2,4-Dichloro-N- [4- (1H-indol-5-ylmethyleneaminooxy) benzoyl] benzenesulfonamide
IRν (ATR) cm ^-1 ; 1693
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 6.52-6.57 (1H, m), 7.32-7.38 (2H, m), 7.41-7.47 (1H, m), 7.49 (1H, d , J = 8.6 Hz), 7.63 (1H, dd, J = 8.6, 1.4 Hz), 7.73 (1H, dd, J = 8.8, 2.2 Hz), 7.90 (1H, d, J = 2.2 Hz), 7.95-8.01 (3H, m), 8.17 (1H, d, J = 8.8 Hz), 8.79 (1H, s), 11.39-11.47 (1H, br), 12.65-13.25 (1H, br).

Example 16
(E) -N- [4- (1-Ethyl-2,3-dihydro-1H-indole-5-ylmethyleneaminooxy) benzoyl] -4-methoxybenzenesulfonamide
IRν (ATR) cm ^-1 ; 2157, 1697, 1598
¹ H-NMR (CDCl ₃ , 400 MHz) δ (ppm); 1.19 (3H, t, J = 7.3 Hz), 3.02 (2H, t, J = 8.5 Hz), 3.23 (2H, q, J = 7.3 Hz) ), 3.50 (2H, t, J = 8.5 Hz), 3.87 (3H, s), 6.36-6.41 (1H, m), 6.98-7.04 (2H, m), 7.22-7.40 (4H, m), 7.69- 7.78 (2H, m), 8.07-8.14 (2H, m), 8.27 (1H, s), 8.45-8.56 (1H, br).

Example 17
(E) -N- [4- (1-Ethyl-2,3-dihydro-1H-indol-5-ylmethyleneaminooxy) benzoyl] -3,5-dimethylbenzenesulfonamide
IRν (ATR) cm ^-1 ; 1683
¹ H-NMR (CDCl ₃ , 400 MHz) δ (ppm); 1.19 (3H, t, J = 7.3 Hz), 2.40 (6H, s), 3.02 (2H, t, J = 8.5 Hz), 3.23 (2H , q, J = 7.3 Hz), 3.50 (2H, t, J = 8.5 Hz), 6.38 (1H, d, J = 8.5 Hz), 7.23-7.30 (5H, m), 7.71-7.79 (4H, m) , 8.28 (1H, s), 8.50-8.58 (1H, br).

Example 18
(E) -N- [4- (4-Hexylbenzylideneaminooxy) benzoyl] -2,4-dichlorobenzenesulfonamide
IRν (ATR) cm ^-1 ; 1695
¹ H-NMR (CDCl ₃ , 400 MHz) δ (ppm); 0.84-0.93 (3H, m), 1.25-1.40 (6H, m), 1.59-1.70 (2H, m), 2.60-2.70 (2H, m ), 7.22-7.26 (2H, m), 7.30-7.35 (2H, m), 7.49 (1H, dd, J = 2.0, 8.5 Hz), 7.52 (1H, d, J = 2.0 Hz), 7.59-7.66 ( 2H, m), 7.75-7.84 (2H, m), 8.31 (1H, d, J = 8.5 Hz), 8.40 (1H, s), 8.85-8.93 (1H, br).

Example 19
(E) -N- [4- (4-Isopropylbenzylideneaminooxy) benzoyl] -2,4,6-trifluorobenzenesulfonamide
IRν (ATR) cm ^-1 ; 1691
¹ H-NMR (CDCl ₃ , 400 MHz) δ (ppm); 1.27 (6H, d, J = 7.1 Hz), 2.88-3.03 (1H, m), 6.77-6.88 (2H, m), 7.28-7.36 ( 4H, m), 7.60-7.69 (2H, m), 7.77-7.86 (2H, m), 8.41 (1H, s), 8.96-9.10 (1H, br).

Example 20
(E) -2,4-Dichloro-N- [4- (1-ethyl-2,3-dihydro-1H-indole-5-ylmethyleneaminooxy) benzoyl] benzenesulfonamide
IRν (ATR) cm ^-1 ; 1691, 1600, 1570, 1502.
¹ H-NMR (CDCl ₃ , 400 MHz) δ (ppm); 1.19 (3H, t, J = 7.2 Hz), 3.01 (2H, t, J = 8.3 Hz), 3.22 (2H, q, J = 7.2 Hz) ), 3.49 (2H, t, J = 8.3 Hz), 6.38 (1H, d, J = 8.4 Hz), 7.24-7.31 (2H, m), 7.45-7.54 (3H, m), 7.75-7.80 (2H, m), 8.27 (1H, s), 8.31 (1H, d, J = 8.4 Hz), 8.52 (1H, s), 8.95-9.19 (1H, br).

Example 21
(E) -N- [4- (1-Ethyl-2,3-dihydro-1H-indole-5-ylmethyleneaminooxy) benzoyl] benzenesulfonamide
IRν (ATR) cm ^-1 ; 1687, 1599, 1504.
¹ H-NMR (CDCl ₃ , 400 MHz) δ (ppm); 1.19 (3H, t, J = 7.1 Hz), 3.01 (2H, t, J = 8.3 Hz), 3.22 (2H, q, J = 7.1 Hz) ), 3.49 (2H, t, J = 8.3 Hz), 6.33-6.42 (1H, m), 7.20-7.32 (3H, m), 7.47-7.68 (4H, m), 7.73-7.83 (2H, m), 8.13-8.22 (2H, m), 8.26 (1H, s), 8.80-9.15 (1H, br).

Example 22
(E) -2-Chloro-N- [4- (1-ethyl-2,3-dihydro-1H-indole-5-ylmethyleneaminooxy) benzoyl] benzenesulfonamide
IRν (ATR) cm ^-1 ; 1691, 1594, 1508.
¹ H-NMR (CDCl ₃ , 400 MHz) δ (ppm); 1.19 (3H, t, J = 7.3 Hz), 3.02 (2H, t, J = 8.3 Hz), 3.22 (2H, q, J = 7.3 Hz) ), 3.49 (2H, t, J = 8.3 Hz), 6.33-6.43 (1H, m), 7.22-7.33 (3H, m), 7.45-7.61 (4H, m), 7.74-7.84 (2H, m), 8.27 (1H, s), 8.34-8.43 (1H, m), 8.90-9.30 (1H, br).

Example 23
(E) -4-Chloro-N- [4- (1-ethyl-2,3-dihydro-1H-indole-5-ylmethyleneaminooxy) benzoyl] benzenesulfonamide
IRν (ATR) cm ^-1 ; 1712, 1600, 1568.
¹ H-NMR (CDCl ₃ , 400 MHz) δ (ppm); 1.19 (3H, t, J = 7.1 Hz), 3.01 (2H, t, J = 8.3 Hz), 3.22 (2H, q, J = 7.3 Hz) ), 3.49 (2H, t, J = 8.3 Hz), 6.33-6.44 (1H, m), 7.21-7.32 (3H, m), 7.45-7.59 (3H, m), 7.70-7.81 (2H, m), 8.05-8.15 (2H, m), 8.27 (1H, s), 8.70-9.10 (1H, br).

Example 24
(E) -N- [4- (1-Ethyl-2,3-dihydro-1H-indole-5-ylmethyleneaminooxy) benzoyl] -4-fluorobenzenesulfonamide
IRν (ATR) cm ^-1 ; 1712, 1600, 1568.
¹ H-NMR (CDCl ₃ , 400 MHz) δ (ppm); 1.19 (3H, t, J = 7.1 Hz), 3.02 (2H, t, J = 8.3 Hz), 3.22 (2H, q, J = 7.3 Hz) ), 3.49 (2H, t, J = 8.3 Hz), 6.33-6.43 (1H, m), 7.16-7.36 (5H, m), 7.50 (1H, s), 7.70-7.82 (2H, m), 8.14- 8.25 (2H, m), 8.27 (1H, s), 8.70-9.10 (1H, br).

Example 25
(E) -2,4-Dichloro-N- [4- (4-diethylaminobenzylideneaminooxy) benzoyl] benzenesulfonamide
IRν (ATR) cm ^-1 ; 1691, 1594, 1525, 1506.
¹ H-NMR (CDCl ₃ , 400 MHz) δ (ppm); 1.20 (6H, t, J = 7.1 Hz), 3.40 (4H, t, J = 7.1 Hz), 6.60-6.72 (2H, m), 7.25 -7.32 (2H, m), 7.45-7.59 (4H, m), 7.74-7.83 (2H, m), 8.30 (1H, s), 8.31-8.35 (1H, m), 8.80-9.30 (1H, br) .

Example 26
(E) -2,4-Dichloro-N- [4- (1-methyl-2,3-dihydro-1H-indole-5-ylmethyleneaminooxy) benzoyl] benzenesulfonamide
IRν (ATR) cm ^-1 ; 1689, 1597, 1568, 1504.
¹ H-NMR (CDCl ₃ , 400 MHz) δ (ppm); 2.83 (3H, s), 3.01 (2H, t, J = 8.3 Hz), 3.45 (2H, t, J = 8.3 Hz), 6.35-6.44 (1H, m), 7.23-7.33 (3H, m), 7.45-7.55 (3H, m), 7.74-7.83 (2H, m), 8.28 (1H, s), 8.32 (1H, d, J = 8.5 Hz ), 8.52 (1H, s), 8.90-9.40 (1H, br).

Example 27
(E) -2,4-Dichloro-N- [4- (1-isopropyl-2,3-dihydro-1H-indol-5-ylmethyleneaminooxy) benzoyl] benzenesulfonamide
IRν (ATR) cm ^-1 ; 1691, 1599, 1570, 1504.
¹ H-NMR (CDCl ₃ , 400 MHz) δ (ppm); 1.19 (6H, d, J = 6.6 Hz), 3.00 (2H, t, J = 8.3 Hz), 3.45 (2H, t, J = 8.3 Hz) ), 3.80-3.94 (1H, m), 6.36 (1H, d, J = 8.3 Hz), 7.22-7.35 (3H, m), 7.42-7.57 (3H, m), 7.73-7.84 (2H, m), 8.27 (1H, s), 8.31 (1H, d, J = 8.3 Hz), 8.80-9.40 (1H, br).

Example 28
(E) -2,4-Dichloro-N- [4- (4-dimethylaminobenzylideneaminooxy) benzoyl] benzenesulfonamide
IRν (ATR) cm ^-1 ; 1693, 1593, 1527, 1506.
¹ H-NMR (CDCl ₃ , 400 MHz) δ (ppm); 3.04 (6H, s), 6.66-6.74 (2H, m), 7.26-7.33 (2H, m), 7.46-7.53 (2H, m), 7.52-7.61 (2H, m), 7.75-7.83 (2H, m), 8.31 (1H, s), 8.32 (1H, d, J = 8.3 Hz), 8.80-9.30 (1H, br).

Example 29
2,4-Dichloro-N- [4- (5-isopropylthiophen-2-ylmethyleneaminooxy) benzoyl] benzenesulfonamide
IRν (ATR) cm ^-1 ; 1687
¹ H-NMR (CDCl ₃ , 400 MHz) δ (ppm); 1.26 (2H, d, J = 6.8 Hz), 1.27 (4H, d, J = 6.8 Hz), 2.91-3.06 (1H, m), 7.29 (1H, s), 7.28-7.37 (1H, m), 7.35-7.43 (2H, m), 7.49 (1H, dd, J = 2.0, 8.6 Hz), 7.52 (1H, d, J = 2.0 Hz), 7.74-7.85 (2H, m), 7.88 (0.8H, s), 8.31 (1H, d, J = 8.6 Hz), 8.52 (0.2H, s), 8.85-8.95 (1H, br).

Example 30
(E) -N- [4- (4-Isopropylbenzylideneaminooxy) benzoyl] -2,4-dimethylbenzenesulfonamide
IRν (ATR) cm ^-1 ; 1697
¹ H-NMR (CDCl ₃ , 400 MHz) δ (ppm); 1.27 (6H, d, J = 6.8 Hz), 2.37 (3H, s), 2.67 (3H, s), 2.89-3.03 (1H, m) , 7.10 (1H, s), 7.21 (1H, d, J = 8.3 Hz), 7.27-7.36 (4H, m), 7.61-7.69 (1H, m), 7.74-7.85 (2H, m), 8.15 (1H , d, J = 8.3 Hz), 8.40 (1H, s), 8.73-8.96 (1H, br).

Example 31
(E) -N- [4- (4-Isopropylbenzylideneaminooxy) benzoyl] -2,4-difluorobenzenesulfonamide
IR ν (ATR) cm ^-1 ; 1706
¹ H-NMR (CDCl ₃ , 400 MHz) δ (ppm); 1.27 (6H, d, J = 6.8 Hz), 2.90-3.02 (1H, m), 6.90-7.00 (1H, m), 7.04-7.14 ( 1H, m), 7.28-7.36 (4H, m), 7.61-7.68 (1H, m), 7.74-7.82 (2H, m), 8.18-8.28 (1H, m), 8.41 (1H, s), 8.83- 8.91 (1H, br).

Example 32
(E) -N- [4- (1-Ethyl-2,3-dihydro-1H-indol-5-ylmethyleneaminooxy) benzoyl] -4-methoxybenzenesulfonamide sodium salt
IRν (ATR) cm ^-1 ; 1597, 1568, 1498.
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 1.11 (3H, t, J = 7.3 Hz), 2.96 (2H, t, J = 8.3 Hz), 3.21 (2H, q, J = 7.3 Hz), 3.44 (2H, t, J = 8.3 Hz), 3.77 (3H, s), 6.49 (1H, d, J = 8.2 Hz), 6.85-6.92 (2H, m), 7.04-7.10 (2H, m), 7.34 (1H, d, J = 8.2 Hz), 7.48 (1H, s), 7.72-7.79 (2H, m), 7.83-7.89 (2H, m), 8.44 (1H, s).

Example 33
2,4-Dichloro-N- [6- (4-isopropylphenoxy) benzofuran-2-carbonyl] benzenesulfonamide sodium salt

(1) 2-Hydroxy-4-methoxybenzaldehyde (25.0 g) is dissolved in DMF (250 mL), methyl bromoacetate (32.5 g) and K ₂ CO ₃ (62.5 g) are added, and one hour at 70 ° C. Stir. Insoluble material was filtered off, water was added, and the mixture was extracted with AcOEt. The organic layer was washed with saturated brine, dried (Na ₂ SO ₄ ), and the solvent was evaporated under reduced pressure. The obtained residue was dissolved in toluene (250 mL), DBU (35.0 g) was added, and the mixture was stirred at 130 ° C. for 14 hr. The solvent was evaporated under reduced pressure, and the resulting residue was dissolved in MeOH (200 mL), concentrated hydrochloric acid (25 mL) was added, and the mixture was stirred at 70 ° C. for 6 hr. The solvent was distilled off under reduced pressure, AcOEt was added to the resulting residue, and the mixture was neutralized with saturated aqueous sodium bicarbonate under ice cooling. The organic layer was washed with saturated brine, dried (Na ₂ SO ₄ ), and the solvent was evaporated under reduced pressure. The obtained residue was dissolved in CH ₂ Cl ₂ (150 mL), BBr ₃ (27.0 g) was added under ice cooling, and the mixture was stirred at room temperature for 24 hours. The solvent was removed under reduced pressure, and the resulting residue was dissolved in MeOH (110 mL), concentrated hydrochloric acid (11 mL) was added, and the mixture was stirred at 70 ° C. for 14 hr. The solvent was distilled off under reduced pressure, AcOEt was added to the resulting residue, and the mixture was neutralized with saturated aqueous sodium bicarbonate under ice cooling. The two layers were separated, and the organic layer was washed with saturated brine, dried (Na ₂ SO ₄ ), and the solvent was evaporated under reduced pressure. The obtained residue was purified by column chromatography, and the solvent of the target fraction was distilled off under reduced pressure. N-Hexane was added to the obtained residue, and the precipitate was collected by filtration to obtain a slightly yellow powder (5.30 g) of methyl 6-hydroxybenzofuran-2-carboxylate.
¹ H-NMR (CDCl ₃ + CD ₃ OD, 400 MHz) δ (ppm); 3.95 (3H, s), 6.87 (1H, dd, J = 8.6, 2.0 Hz), 6.99-7.02 (1H, m), 7.45 (1H, d, J = 1.0 Hz), 7.50 (1H, d, J = 8.6 Hz).

(2) The compound (960 mg) obtained in (1) and 4-isopropylphenylboronic acid (1.64 g, 10.0 mmol) were dissolved in CH ₂ Cl ₂ (20 mL), and copper (II) acetate (Cu ( OAc) ₂ ) (910 mg), pyridine (2.0 mL) and 4A molecular sieves (750 mg) were added, and the mixture was stirred at 30 ° C. for 12 hours in an oxygen atmosphere. The reaction mixture was filtered through celite, CH ₂ Cl ₂ was added to the filtrate, washed with 10% aqueous citric acid solution and saturated brine, and dried (Na ₂ SO ₄ ). The solvent was distilled off under reduced pressure, and the resulting residue was purified by column chromatography, and then the solvent of the target fraction was distilled off under reduced pressure. The obtained yellow oil of methyl 6- (4-isopropylphenoxy) benzofuran-2-carboxylate was dissolved in MeOH (20 mL), 1.0 M LiOH aqueous solution (8.0 mL) was added, and the mixture was stirred at 70 ° C. for 0.5 hr. did. MeOH was distilled off under reduced pressure, and the resulting residue was acidified with 10% aqueous citric acid solution under ice cooling, and then extracted with AcOEt. The organic layer was washed with saturated brine, dried (Na ₂ SO ₄ ), and the solvent was evaporated under reduced pressure. N-Hexane was added to the obtained residue, and the precipitate was collected by filtration to obtain a white powder (1.10 g) of 6- (4-isopropylphenoxy) benzofuran-2-carboxylic acid.
¹ H-NMR (CDCl ₃ , 400 MHz) δ (ppm); 1.27 (6H, d, J = 6.8 Hz), 2.87-2.98 (1H, m), 6.97-7.02 (2H, m), 7.06 (1H, dd, J = 8.6, 2.2 Hz), 7.09-7.12 (1H, m), 7.20-7.25 (2H, m), 7.61 (1H, d, J = 8.6 Hz), 7.64 (1H, d, J = 0.7 Hz ).

(3) The compound (296 mg) obtained in (2) was dissolved in DMF (3 mL), CDI (172 mg) was added, and the mixture was stirred at room temperature for 0.5 hour, and then 2,4-dichlorobenzenesulfonamide ( 226 mg) and DBU (0.14 mL) were added, and the mixture was stirred at room temperature for 64 hours. A 10% aqueous citric acid solution was added and the mixture was extracted with AcOEt. The organic layer was washed successively with water and saturated brine and dried (Na ₂ SO ₄ ). The solvent was distilled off under reduced pressure, and the resulting residue was purified by column chromatography, and then the solvent of the target fraction was distilled off under reduced pressure. The obtained colorless oil (300 mg) was dissolved in THF (1 mL), 5.0 M sodium methoxide-MeOH (0.12 mL) was added under ice cooling, and the mixture was stirred at room temperature for 1 hr. Et ₂ O and n-hexane were added, and insoluble matters were filtered off. After the filtrate was concentrated, the obtained oil was dissolved in MeOH, Et ₂ O and n-hexane were added, and the mixture was stirred at room temperature for 1 hr. The precipitate was collected by filtration to give the title compound as a white powder (210 mg).
IRν (ATR) cm ^-1 ; 1601
¹ H-NMR (CDCl ₃ + CD ₃ OD, 400 MHz) δ (ppm); 1.25 (6H, d, J = 6.8 Hz), 2.86-2.96 (1H, m), 6.91-6.96 (2H, m), 6.96 (1H, dd, J = 8.5, 2.2 Hz), 7.07 (1H, d, J = 2.2 Hz), 7.17-7.22 (2H, m), 7.30 (1H, dd, J = 8.5, 2.2 Hz), 7.37 (1H, s), 7.52 (1H, d, J = 8.5 Hz), 7.43 (1H, d, 2.2 Hz), 8.09 (1H, d, J = 8.5 Hz).

Example 34
2,4-dichloro-N- {6- [2- (4-isopropylphenyl) ethoxy] benzofuran-2-carbonyl} benzenesulfonamide

(1) The compound (199 mg) obtained in (1) of Example 33 and 2- (4-isopropylphenyl) ethyl methanesulfonate (250 mg) were dissolved in DMF (3 mL), and K ₂ CO ₃ ( 285 mg) was added, and the mixture was stirred at 70 ° C. for 6 hours under an argon atmosphere. Water was added, the mixture was extracted with AcOEt, washed with saturated brine, dried (Na ₂ SO ₄ ), and the solvent was evaporated under reduced pressure. The obtained residue was purified by column chromatography, and the solvent of the target fraction was evaporated under reduced pressure to give a colorless oily product of methyl 6- [2- (4-isopropylphenyl) ethoxy] benzofuran-2-carboxylate ( 230 mg) was obtained.
¹ H-NMR (CDCl ₃ , 400 MHz) δ (ppm); 1.25 (6H, d, J = 6.8 Hz), 2.83-2.95 (1H, m), 3.10 (2H, t, J = 7.3 Hz), 3.94 (3H, s), 4.20 (2H, t, J = 7.3Hz), 6.93 (1H, dd, J = 8.8, 2.2 Hz), 7.04 (1H, d, J = 2.2 Hz), 7.16-7.25 (4H, m), 7.45 (1H, s), 7.51 (1H, d, J = 8.8 Hz).

(2) Dissolve the compound (230 mg) obtained in (1) in MeOH-THF (1: 1) (4 mL), add 1.0 M LiOH aqueous solution (2.0 mL), and stir at 70 ° C. for 1 hour. did. After allowing to cool, 1M hydrochloric acid (2.0 mL) was added, and the solvent was evaporated under reduced pressure. The precipitate was filtered off and washed with water to give a white powder (210 mg) of 6- [2- (4-isopropylphenyl) ethoxy] benzofuran-2-carboxylic acid.
¹ H-NMR (CDCl ₃ , 400 MHz) δ (ppm); 1.25 (6H, d, J = 6.8 Hz), 2.85-2.95 (1H, m), 3.10 (2H, t, J = 7.3 Hz), 4.22 (2H, t, J = 7.3 Hz), 6.94 (1H, dd, J = 8.8, 2.2 Hz), 7.04 (1H, d, J = 2.2 Hz), 7.16-7.25 (4H, m), 7.47 (1H, s), 7.52 (1H, d, J = 8.8 Hz).

(3) The compound (210 mg) obtained in (2) was dissolved in DMF (3 mL), CDI (111 mg) was added, and the mixture was stirred at room temperature for 0.5 hour, and then 2,4-dichlorobenzenesulfonamide ( 146 mg) and DBU (0.09 mL) were added, and the mixture was stirred at room temperature for 36 hours. A 10% aqueous citric acid solution was added and the mixture was extracted with AcOEt. The organic layer was washed with saturated brine and dried (Na ₂ SO ₄ ), and the solvent was evaporated under reduced pressure. The obtained residue was purified by column chromatography, and the solvent of the target fraction was distilled off under reduced pressure. N-Hexane was added to the obtained residue, and the precipitate was collected by filtration to give the title compound as a white powder (15 mg).
IRν (ATR) cm ^-1 ; 1691
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 1.16 (6H, d, J = 6.8 Hz), 2.78-2.89 (1H, m), 3.00 (2H, t, J = 6.4 Hz) , 4.23 (2H, t, J = 6.4 Hz), 6.95 (1H, d, J = 8.0 Hz), 7.13-7.28 (5H, m), 7.66 (1H, d, J = 8.6Hz), 7.93 (1H, s), 7.70 (1H, d, J = 8.0 Hz), 7.87 (1H, s), 8.14 (1H, d, J = 8.6 Hz).

Example 35
2,4-Dichloro-N- [6- (9H-carbazol-3-yloxy) benzofuran-2-carbonyl] benzenesulfonamide

(1) 3-Bromo-9H-carbazole (5.00 g) dissolved in THF (100 mL), di-tert-butyl dicarbonate (Boc ₂ O) (5.32 g) and N, N-dimethyl-4-amino Pyridine (DMAP) (489 mg) was added and stirred at room temperature for 5 hours. A 10% aqueous citric acid solution was added to the reaction solution, extracted with AcOEt, washed with saturated brine, and dried (Na ₂ SO ₄ ). The solvent was distilled off under reduced pressure, and the resulting residue was purified by column chromatography. The solvent of the target fraction was distilled off under reduced pressure to obtain a colorless oily substance (7.03 g) of tert-butyl 3-bromo-9H-carbazole-9-carboxylate.
¹ H-NMR (CDCl ₃ , 400 MHz) δ (ppm); 1.76 (9H, s), 7.34-7.39 (1H, m), 7.46-7.51 (1H, m), 7.55 (1H, dd, J = 9.1 , 2.2 Hz), 7.90-7.95 (1H, m), 8.08 (1H, d, J = 2.2 Hz), 8.17-8.22 (1H, m), 8.26-8.30 (1H, m).

(2) The compound (4.00 g) obtained in (1) and bis (pinacolato) diboron (3.23 g) are dissolved in 1,4-dioxane (100 mL), and dichlorobis (triphenylphosphine) palladium (II) ( PdCl ₂ (PPh ₃ ) ₂ ) (407 mg) and potassium acetate (AcOK) (3.98 g) were added, and the mixture was stirred at 90 ° C. for 12 hours under an argon atmosphere. AcOEt and water were added to the reaction solution, and the mixture was filtered through celite. The two layers were separated, and the organic layer was washed with saturated brine and dried (Na ₂ SO ₄ ). The solvent was distilled off under reduced pressure, the resulting residue was purified by column chromatography, and the solvent of the target fraction was distilled off under reduced pressure. The obtained colorless oil was dissolved in acetone (130 mL), water (130 mL), ammonium acetate (AcONH ₄ ) (6.17 g) and NaIO ₄ (17.1 g) were added, and the mixture was stirred at 20 ° C. for 15 hr. . AcOEt and water were added to the reaction solution, and the two layers were separated. The organic layer was washed with saturated brine and dried (Na ₂ SO ₄ ), and the solvent was evaporated under reduced pressure. The obtained residue was purified by column chromatography, and the solvent of the target fraction was distilled off under reduced pressure. N-Hexane was added to the obtained residue, and the precipitate was collected by filtration to obtain a white powder (2.05 g) of (9-tert-butoxycarbonyl-9H-carbazol-3-yl) boronic acid.
¹ H-NMR (CDCl ₃ , 400 MHz) δ (ppm); 1.71 (9H, s), 7.20 (1H, dd, J = 7.8, 2.2 Hz), 7.35-7.55 (2H, m), 7.65 (1H, d, J = 2.2 Hz), 7.87 (1H, d, J = 7.8 Hz), 8.27-8.33 (2H, m).

(3) The compound (1.00 g) obtained in (1) of Example 66 and the compound (1.62 g) obtained in (2) were dissolved in CH ₂ Cl ₂ (40 mL), and Cu (OAc) ₂ (946 mg), pyridine (2.1 mL), and 4A molecular sieves (700 mg) were added, and the mixture was stirred at 30 ° C. for 12 hours in an oxygen atmosphere. The reaction mixture was filtered through celite, CH ₂ Cl ₂ was added to the filtrate, washed successively with 10% aqueous citric acid solution and saturated brine, dried (Na ₂ SO ₄ ), and the solvent was evaporated under reduced pressure. The obtained residue was purified by column chromatography, the solvent of the target fraction was distilled off under reduced pressure, and methyl 6- (9-tert-butoxycarbonyl-9H-carbazol-3-yloxy) benzofuran-2-carboxylate was obtained. A colorless oil (1.90 g) was obtained.
¹ H-NMR (CDCl ₃ , 400 MHz) δ (ppm); 1.77 (9H, s), 3.95 (3H, s), 7.06 (1H, dd, J = 8.6, 2.2 Hz), 7.19 (1H, d, J = 2.2 Hz), 7.20 (1H, dd, J = 7.8, 2.2 Hz), 7.30-7.35 (1H, m), 7.45-7.50 (1H, m), 7.50 (1H, s), 7.60 (1H, d , J = 8.6 Hz), 7.65 (1H, d, J = 2.2 Hz), 7.87 (1H, d, J = 7.8 Hz), 8.27-8.33 (2H, m).

(4) Dissolve the compound (900 mg) obtained in (3) in MeOH-THF (1: 1) (10 mL), add 1.0 M LiOH aqueous solution (4.0 mL), and stir at 60 ° C. for 1 hour. did. After standing to cool, 1.0 M hydrochloric acid was added, and after neutralization, the precipitate was filtered to obtain a light gray powder (240 mg) of 6- (9H-carbazol-3-yloxy) benzofuran-2-carboxylic acid.
¹ H-NMR (CDCl ₃ , 400 MHz) δ (ppm); 6.99 (1H, s), 7.08 (1H, d, J = 8.6 Hz), 7.13-7.23 (2H, m), 7.36-7.58 (3H, m), 7.77 (1H, s), 7.96 (1H, d, J = 8.6 Hz), 8.02 (1H, s), 8.21-8.27 (1H, m), 8.39 (1H, s).

(5) The compound (178 mg) obtained in (4) was dissolved in DMF (3 mL), CDI (93 mg) was added, and the mixture was stirred at room temperature for 0.5 hour, and then 2,4-dichlorobenzenesulfonamide (129 mg) and DBU (0.09 mL) were added, and the mixture was stirred at room temperature for 12 hours. Water and AcOEt were added, the two layers were separated, the organic layer was washed with saturated brine, dried (Na ₂ SO ₄ ), and the solvent was evaporated under reduced pressure. The obtained residue was purified by column chromatography, and the solvent of the target fraction was distilled off under reduced pressure. The obtained residue was dissolved in Et ₂ O, n-hexane was added, and the precipitate was collected by filtration to give the title compound as a white powder (45 mg).
IRν (ATR) cm ^-1 ; 1618
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 7.02 (1H, d, J = 8.6 Hz), 7.13 (1H, s), 7.08-7.20 (2H, m), 7.34-7.42 ( 1H, m), 7.45-7.55 (2H, m), 7.66 (1H, d, J = 8.6 Hz), 7.75 (1H, d, J = 8.6 H), 7.80-7.92 (3H, m), 8.05-8.10 (1H, m), 8.12 (1H, d, J = 8.6 Hz), 11.31 (1H, s).

Example 36
2,4-Dichloro-N- [6- (benzimidazol-5-yloxy) benzofuran-2-carbonyl] benzenesulfonamide

(1) 5-fluoro-2-nitroaniline (1.22 g) and the compound (1.50 g) obtained in Example 66 (1) were dissolved in DMF (30 mL), and Cs ₂ CO ₃ (3.82 g) And stirred at 80 ° C. for 12 hours under an argon atmosphere. AcOEt and water were added to the reaction solution, two layers were separated, and the organic layer was washed with saturated brine and dried (Na ₂ SO ₄ ). The solvent was distilled off under reduced pressure, and the resulting residue was dissolved in THF and stirred at 5 ° C. for 1 hour. The precipitate was collected by filtration to obtain a yellow powder (1.81 g) of methyl 6- (3-amino-4-nitrophenoxy) benzofuran-2-carboxylate.
¹ H-NMR (CDCl ₃ , 400 MHz) δ (ppm); 3.99 (3H, s), 6.22 (1H, d, J = 2.4 Hz), 6.35 (1H, dd, J = 9.5, 2.4 Hz), 7.07 (1H, dd, J = 8.5, 2.2 Hz), 7.32 (1H, d, J = 2.2 Hz), 7.54 (1H, s), 7.70 (1H, d, J = 8.5 Hz), 8.13 (1H, d, J = 9.5 Hz).

(2) The compound (1.80 g) obtained in (1) was dissolved in AcOH (20 mL), Zn (1.79 g) was added, and the mixture was stirred at 5 ° C for 0.5 hr, and then ethanol (EtOH) (10 mL) And stirred at room temperature for 1 hour. AcOEt and saturated aqueous sodium hydrogen carbonate were added to the reaction solution, the two layers were separated, the organic layer was washed with saturated brine and dried (Na ₂ SO ₄ ), and the solvent was evaporated under reduced pressure. The obtained oil was dissolved in EtOH (50 mL), diethoxymethyl acetate ((EtO) ₂ CHOAc) (2.22 mL) was added, and the mixture was stirred at 80 ° C. for 2 hr. The solvent was distilled off under reduced pressure, and the resulting residue was purified by column chromatography. The solvent of the target fraction was distilled off under reduced pressure to obtain a brown powder (1.54 g) of methyl 6- (benzimidazol-5-yloxy) benzofuran-2-carboxylate.
¹ H-NMR (CDCl ₃ + CD ₃ OD, 400 MHz) δ (ppm); 3.99 (3H, s), 7.05 (1H, dd, J = 8.8, 2.2 Hz), 7.05 (1H, dd, J = 8.8, 2.2 Hz), 7.09 (1H, d, J = 2.2 Hz), 7.32 (1H, d, J = 2.2 Hz), 7.51 (1H, s), 7.60 (1H, d, J = 8.8 Hz), 7.62 (1H , d, J = 8.8 Hz), 8.04 (1H, s).

(3) The compound (1.53 g) obtained in (2) was dissolved in THF (40 mL), Boc ₂ O (1.30 g) and DMAP (218 mg) were added, and the mixture was stirred at 50 ° C. for 0.5 hr. Further, Boc ₂ O (300 mg) was added and stirred at 50 ° C. for 1 hour. AcOEt and water were added to the reaction solution, the two layers were separated, and the organic layer was washed successively with 10% aqueous citric acid solution and saturated brine, and dried (Na ₂ SO ₄ ). The solvent was distilled off under reduced pressure, and the resulting residue was purified by column chromatography. The solvent of the target fraction was distilled off under reduced pressure, n-hexane was added to the resulting residue, the precipitate was collected by filtration, and tert-butyl 5- (2-methoxycarbonylbenzofuran-6-yloxy) benzimidazole-1 A white powder (1.41 g) of (3) -carboxylate was obtained.
¹ H-NMR (CDCl ₃ , 400 MHz) δ (ppm); 1.62 (6H, s), 1.71 (3H, s), 3.96 (3H, s), 7.02-7.20 (3H, m), 7.44-7.68 ( 4H, m), 7.75 (0.67H, d, J = 8.8 Hz), 7.97 (0.33H, d, J = 8.8 Hz), 8.40 (0.67H, s), 8.45 (0.33H, s).

(4) The compound (1.40 g) obtained in (3) was suspended in MeOH-THF (1: 1) (15 mL), 1.0 M LiOH aqueous solution (7.0 mL) was added, and the mixture was stirred at 60 ° C. for 1 hour. did. After allowing to cool, the precipitate was collected by filtration, dissolved in DMSO, 10% aqueous citric acid solution was added, the precipitate was collected by filtration, and a slightly brownish 6- (benzimidazol-5-yloxy) benzofuran-2-carboxylic acid was obtained. A powder (880 mg) was obtained.
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 6.98 (1H, dd, J = 8.5, 2.2 Hz), 7.02 (1H, dd, J = 8.5, 2.0 Hz), 7.24 (1H, d, J = 2.0 Hz), 7.27 (1H, d, J = 2.2 Hz), 7.63 (1H, s), 7.62 (1H, d, J = 8.8 Hz), 7.72 (1H, d, J = 8.8 Hz) , 8.25 (1H, s).

(5) The compound (294 mg) obtained in (4) was dissolved in DMF (4 mL), CDI (178 mg) was added, and the mixture was stirred at room temperature for 0.5 hour, and then 2,4-dichlorobenzenesulfonamide ( 249 mg) and DBU (0.14 mL) were added, and the mixture was stirred at room temperature for 12 hours. Water and AcOEt were added to the reaction solution, the two layers were separated, the organic layer was washed with saturated brine, dried (Na ₂ SO ₄ ), and the solvent was evaporated under reduced pressure. THF and Et ₂ O were added to the obtained residue, and the precipitate was collected by filtration. THF was added to the obtained powder, and the mixture was stirred at room temperature for 1 hour and collected by filtration to obtain the title compound as a pale yellow powder (90 mg).
IRν (ATR) cm ^-1 ; 1697
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 7.02 (1H, d, J = 8.8 Hz), 7.20 (1H, d, J = 9.0 Hz), 7.28 (1H, s), 7.45 (1H, d, J = 8.8 Hz), 7.54 (1H, s), 7.65 (1H, s), 7.69-7.79 (2H, m), 8.03 (1H, d, J = 8.8 Hz), 9.04 (1H, s).

Example 37
2,4-Dichloro-N- [5- (biphenyl-4-yloxy) benzofuran-2-carbonyl] benzenesulfonamide

(1) Ethyl 5-hydroxybenzofuran-2-carboxylate (400 mg) and 4-biphenylboronic acid (824 mg) are dissolved in CH ₂ Cl ₂ (10 mL), Cu (OAc) ₂ (378 mg), Pyridine (0.83 mL) and 4A molecular sieves (300 mg) were added, and the mixture was stirred at 30 ° C. for 12 hours in an oxygen atmosphere. The reaction solution was filtered through Celite, CH ₂ Cl ₂ was added to the filtrate, and the mixture was washed successively with 10% aqueous citric acid solution and saturated brine, and dried (Na ₂ SO ₄ ). The solvent was distilled off under reduced pressure, and the resulting residue was purified by column chromatography, and then the solvent of the target fraction was distilled off under reduced pressure. Dissolve the colorless oil of ethyl 5- (biphenyl-4-yloxy) benzofuran-2-carboxylate in MeOH-THF (1: 1) (14 mL) and add 1.0 M LiOH aqueous solution (7.9 mL). And stirred at 60 ° C. for 1 hour. After cooling, the mixture was neutralized with 1.0 M hydrochloric acid, and the precipitate was collected by filtration. Washing with water and MeOH gave white powder (334 mg) of 5- (biphenyl-4-yloxy) benzofuran-2-carboxylic acid.
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 7.03-7.08 (2H, m), 7.16 (1H, dd, J = 8.8, 2.4 Hz), 7.28 (1H, s), 7.26- 7.37 (1H, m), 7.35 (1H, d, J = 2.4 Hz), 7.40-7.46 (2H, m), 7.60-7.68 (5H, m).

(2) The compound (301 mg) obtained in (1) was dissolved in DMF (4 mL), CDI (156 mg) was added, and the mixture was stirred at room temperature for 0.5 hour, followed by 2,4-dichlorobenzenesulfonamide ( 226 mg) and DBU (0.12 mL) were added, and the mixture was stirred at room temperature for 12 hours. Water and AcOEt were added, the two layers were separated, the organic layer was washed with saturated brine, dried (Na ₂ SO ₄ ), and the solvent was evaporated under reduced pressure. The obtained residue was purified by column chromatography, and the solvent of the target fraction was distilled off under reduced pressure. The obtained residue was dissolved in AcOEt, Et ₂ O was added, and the precipitate was collected by filtration to give the title compound as a white powder (50 mg).
IRν (ATR) cm ^-1 ; 1574
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 6.97-7.02 (2H, m), 7.06 (1H, dd, J = 8.6, 2.2 Hz), 7.13 (1H, s), 7.25- 7.30 (1H, m), 7.29 (1H, d, J = 2.2 Hz), 7.34-7.40 (2H, m), 7.43 (1H, dd, J = 8.6, 2.0 Hz), 7.50 (1H, d, J = 2.0 Hz), 7.53-7.62 (4H, m), 7.58 (1H, d, J = 8.8 Hz), 7.93 (1H, d, J = 8.6 Hz).

Example 38
2,4-Dichloro-N- {6- [4- (trifluoromethyl) phenoxy] benzofuran-2-carbonyl} benzenesulfonamide sodium salt

(1) 4-trifluorophenylboronic acid (790 mg) and the compound (400 mg) obtained in Example 66 (1) were dissolved in CH ₂ Cl ₂ (10 mL), and Cu (OAc) ₂ ( 378 mg), pyridine (0.83 mL) and 4A molecular sieves (300 mg) were added, and the mixture was stirred at 30 ° C. for 12 hours in an oxygen atmosphere. The reaction solution was filtered through Celite, CH ₂ Cl ₂ was added to the filtrate, washed with 10% aqueous citric acid solution and saturated brine, and dried (Na ₂ SO ₄ ). The solvent was distilled off under reduced pressure, and the resulting residue was purified by column chromatography, and then the solvent of the target fraction was distilled off under reduced pressure to give methyl 6- [4- (trifluoromethyl) phenoxy] benzofuran-2- A pale yellow powder (550 mg) of carboxylate was obtained. ¹ H-NMR (CDCl ₃ , 400 MHz) δ (ppm); 3.98 (3H, s), 7.05 (1H, dd, J = 8.6, 2.0 Hz), 7.06-7.11 (2H, m), 7.24-7.26 ( 1H, m), 7.53 (1H, d, J = 1.0 Hz), 7.58-7.63 (2H, m), 7.67 (1H, d, J = 8.6 Hz).

(2) Dissolve the compound (550 mg) obtained in (1) in MeOH-THF (1: 1) (6 mL), add 1.0 M LiOH aqueous solution (3.0 mL), and stir at 30 ° C. for 12 hours. did. 1.0 M hydrochloric acid (3.0 mL) was added, MeOH was distilled off under reduced pressure, AcOEt and water were added to the resulting residue, the two layers were separated, the organic layer was washed with saturated brine, and dried (Na ₂ SO ₄ )did. The solvent was distilled off under reduced pressure to obtain 6- (4-trifluorophenylphenoxy) benzofuran-2-carboxylic acid white powder (269 mg).
¹ H-NMR (CDCl ₃ , 400 MHz) δ (ppm); 7.02 (1H, d, J = 8.6 Hz), 7.06-7.11 (2H, m), 7.24 (1H, s), 7.43 (1H, s) , 7.57-7.62 (2H, m), 7.65 (1H, d, J = 8.6 Hz).

(3) The compound (265 mg) obtained in (2) was dissolved in DMF (5 mL), CDI (147 mg) was added, and the mixture was stirred at room temperature for 0.5 hour, and then 2,4-dichlorobenzenesulfonamide ( 205 mg) and DBU (0.10 mL) were added, and the mixture was stirred at room temperature for 12 hours. A 10% aqueous citric acid solution and AcOEt were added to separate the layers. The aqueous layer was extracted with AcOEt, and then the organic layers were combined, washed successively with water and saturated brine, dried (Na ₂ SO ₄ ), and the solvent was evaporated under reduced pressure. The obtained residue was purified by column chromatography, and the solvent of the target fraction was distilled off under reduced pressure. The obtained oil (130 mg) was dissolved in MeOH-THF (1: 1) (1 mL), sodium methoxide (MeONa) (14 mg) was added under ice cooling, and the mixture was stirred at room temperature for 1 hr. n-Hexane was added, and the mixture was stirred at 5 ° C. for 1 hr, and the precipitate was collected by filtration to give the title compound as a white powder (100 mg).
IRν (ATR) cm ^-1 ; 1597
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 7.03 (1H, d, J = 8.5 Hz), 7.11-7.17 (2H, m), 7.21 (1H, s), 7.44 (1H, s), 7.48 (1H, d, J = 8.5 Hz), 7.55 (1H, s), 7.67-7.75 (3H, m), 7.99 (1H, d, J = 8.5 Hz).

Example 39
N- [4- (4-tert-Butylbenzyloxymethyl) benzoyl] -2,4-dichlorobenzenesulfonamide

(1) 4-tert-butylbenzyl alcohol (578 mg) is dissolved in THF (12 mL), methyl 4-bromomethylbenzoate (403 mg) is added, and NaH (60%) is added in portions under ice cooling. Stir at room temperature for 17 hours. To the reaction solution were added 2.0 M NaOH aqueous solution (3.5 mL) and MeOH (3 mL), and the mixture was stirred at 45 ° C. for 3 hours. Water (20 mL) and Et ₂ O (20 mL) were added, the aqueous layer was separated, adjusted to pH 3 with 10% aqueous citric acid solution, and extracted with AcOEt. The organic layer was washed successively with water and saturated brine, dried (Na ₂ SO ₄ ), and the solvent was evaporated under reduced pressure. The obtained residue was dissolved in Et ₂ O (2 mL), n-hexane (10 mL) was added, and the mixture was stirred under ice-cooling for 30 min. After the precipitate was filtered off, the solvent of the filtrate was distilled off under reduced pressure. After the residue obtained was purified by column chromatography, the solvent of the target fraction was distilled off under reduced pressure to give 4- (4-tert- A white powder (100 mg) of butylbenzyloxymethyl) benzoic acid was obtained.
¹ H-NMR (CDCl ₃ , 400 MHz) δ (ppm); 1.33 (9H, s), 4.57 (2H, s), 4.63 (2H, s), 7.28-7.35 (2H, m), 7.36-7.43 ( 2H, m), 7.43-7.53 (2H, m), 8.06-8.14 (2H, m).

(2) The compound (100 mg) obtained in (1) was dissolved in DMF (1 mL), CDI (60 mg) was added, and the mixture was stirred at room temperature for 1 hour. 2,4-Dichlorobenzenesulfonamide (85 mg) and DBU (0.06 mL) were added, and the mixture was stirred at room temperature for 11 hours. To the reaction solution were added 10% aqueous citric acid solution (10 mL) and AcOEt (10 mL), and the organic layer was separated. Then, the aqueous layer was extracted with AcOEt (10 mL), and the organic layers were combined. After sequentially washing and drying (Na ₂ SO ₄ ), the solvent was distilled off under reduced pressure. The obtained residue was purified by column chromatography, and the solvent of the target fraction was distilled off under reduced pressure. The obtained colorless oil (200 mg) was dissolved in Et ₂ O (3 mL), n-hexane (25 mL) was added under ice cooling, and the mixture was stirred at the same temperature for 1 hr. The precipitate was collected by filtration to give the title compound as a white powder (120 mg).
IRν (ATR) cm ^-1 ; 1691, 1610
¹ H-NMR (CDCl ₃ , 400 MHz) δ (ppm); 1.32 (9H, s), 4.55 (2H, s), 4.59 (2H, s), 7.25-7.31 (2H, m), 7.35-7.40 ( 2H, m), 7.43-7.49 (2H, m), 7.47-7.53 (2H, m), 7.73-7.78 (2H, m), 8.31 (1H, d, J = 8.5 Hz), 8.88-9.01 (1H, br).

Example 40
2,4-Dichloro-N- [4- (5-phenylindan-2-yloxy) benzoyl] benzenesulfonamide sodium salt

(1) 5-Bromoindan-2-yl acetate (1.04 g) was dissolved in 1,4-dioxane (18 mL), phenylboronic acid (547 mg), K ₂ CO ₃ (1.69 g) in water (9 mL) solution and tetrakis (triphenylphosphine) palladium (0) (Pd (PPh ₃ ) ₄ ) (943 mg) were added, and the mixture was stirred at 80 ° C. for 7 hours and at room temperature for 10 hours under a nitrogen stream. AcOEt (70 mL) and water (50 mL) were added to the reaction solution, the insoluble material was filtered off, the organic layer was separated, washed successively with saturated brine, dried (Na ₂ SO ₄ ), and the solvent under reduced pressure Was distilled off. The obtained residue was purified by column chromatography, and the solvent of the target fraction was distilled off under reduced pressure to obtain yellow powder (700 mg) of 5-phenylindan-2-yl acetate.
¹ H-NMR (CDCl ₃ , 400 MHz) δ (ppm); 2.04 (3H, s), 3.00-3.12 (2H, m), 3.30-3.41 (2H, m), 5.54-5.60 (1H, m), 7.28-7.35 (2H, m), 7.38-7.45 (3H, m), 7.46 (1H, s), 7.53-7.59 (2H, m).

(2) The compound (700 mg) obtained in (1) was dissolved in THF (10.5 mL) and MeOH (3.5 mL), 1.0 M LiOH aqueous solution (8.31 mL) was added, and the mixture was stirred at room temperature for 30 minutes. To the reaction mixture was added 10% aqueous citric acid solution (20 mL) and AcOEt (30 mL). The organic layer was separated, and the aqueous layer was extracted with AcOEt (10 mL). The organic layers were combined, and added to water and saturated brine. After sequentially washing and drying (Na ₂ SO ₄ ), the solvent was distilled off under reduced pressure to obtain a pale yellow oily substance (640 mg) of 5-phenylindan-2-ol.
¹ H-NMR (CDCl ₃ , 400 MHz) δ (ppm); 1.47-1.85 (1H, br), 2.91-3.03 (2H, m), 3.21-3.33 (2H, m), 4.72-4.78 (1H, m ), 7.29-7.35 (2H, m), 7.38-7.45 (3H, m), 7.47 (1H, s), 7.52-7.59 (2H, m).

(3) The compound (590 mg) obtained in (2) and methyl 4-hydroxybenzoate (428 mg) were suspended in toluene (12 mL), and triphenylphosphine (PPh ₃ ) (1.11 g) was cooled with ice. And 2.2 M diethyl azodicarboxylate (DEAD) -toluene (1.92 mL) were added, and the mixture was stirred at room temperature for 18 hours. Water (20 mL) and AcOEt (20 mL) were added to the reaction solution, the organic layer was separated, washed with saturated brine and dried (Na ₂ SO ₄ ), and the solvent was evaporated under reduced pressure. The obtained residue was purified by column chromatography, and the solvent of the target fraction was distilled off under reduced pressure to obtain a light pink powder (300 mg) of methyl 4- (5-phenylindan-2-yloxy) benzoate.
¹ H-NMR (CDCl ₃ , 400 MHz) δ (ppm); 3.19-3.30 (2H, m), 3.40-3.51 (2H, m), 3.89 (3H, s), 5.25-5.32 (1H, m), 6.91-6.97 (2H, m), 7.29-7.36 (2H, m), 7.39-7.47 (3H, m), 7.47 (1H, s), 7.55-7.60 (2H, m), 7.96-8.02 (2H, m ).

(4) The compound (330 mg) obtained in (3) was dissolved in THF (5.1 mL) and MeOH (1.7 mL), 1.0 M LiOH aqueous solution (2.88 mL) was added, and 1.5 hours at room temperature and 50 Stir for 2 hours at ° C. A 10% aqueous citric acid solution (30 mL) and AcOEt (30 mL) were added to the reaction solution, and the organic layer was separated, washed successively with water and saturated brine, and dried (Na ₂ SO ₄ ). The solvent was distilled off under reduced pressure to obtain a slightly yellow powder (300 mg) of 4- (5-phenylindan-2-yloxy) benzoic acid.

(5) The compound (300 mg) obtained in (4) was dissolved in DMF (3 mL), CDI (162 mg) was added, and the mixture was stirred at room temperature for 1 hour. 2,4-Dichlorobenzenesulfonamide (226 mg) and DBU (0.15 mL) were added, and the mixture was stirred at room temperature for 12 hours. To the reaction solution was added 10% aqueous citric acid solution (20 mL) and AcOEt (20 mL). The organic layer was separated, and the aqueous layer was extracted with AcOEt (20 mL). The organic layers were combined, and water and saturated brine were added. Then, it was washed successively and dried (Na ₂ SO ₄ ), and the solvent was distilled off under reduced pressure. The obtained residue was purified by column chromatography, and the solvent of the target fraction was distilled off under reduced pressure to obtain a powder (360 mg). This powder was dissolved in THF (3 mL), and 5.0 M MeONa-MeOH (0.13 mL) was added dropwise under ice cooling, followed by stirring at the same temperature for 1 hour. Et ₂ O (30 mL) was added, and the mixture was stirred at the same temperature for 30 min. The precipitate was collected by filtration to give the title compound as a white powder (250 mg).
IRν (ATR) cm ^-1 ; 1603
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 3.00-3.14 (2H, m), 3.36-3.49 (2H, m), 5.26-5.34 (1H, m), 6.84-6.90 (2H , m), 7.31-7.38 (2H, m), 7.40-7.49 (4H, m), 7.51 (1H, d, J = 2.0 Hz), 7.54 (1H, s), 7.58-7.67 (2H, m), 7.80-7.87 (2H, m), 7.98 (1H, d, J = 8.3 Hz).

Example 41
N- [4- (2,4-Dichlorophenoxy) benzoyl] octane-1-sulfonamide

(1) 2,4-dichlorophenol (1.00 g) is dissolved in CH ₂ Cl ₂ (20 mL), 4-methoxycarbonylphenylboronic acid (1.65 g), Cu (OAc) ₂ (1.67 g), ground and Dehydrated 4A molecular sieves (930 mg) and pyridine (2.48 mL) were added, and the mixture was stirred at 35 ° C. for 7 hours in an oxygen atmosphere. A 10% aqueous citric acid solution (60 mL) and AcOEt (60 mL) were added to the reaction mixture, the insoluble material was filtered off, and the aqueous layer was extracted with AcOEt (20 mL). The organic layers were combined, washed with saturated brine, dried (Na ₂ SO ₄ ), and the solvent was evaporated under reduced pressure. The obtained residue was purified by column chromatography, and the solvent of the target fraction was distilled off under reduced pressure to obtain methyl 4- (2,4-dichlorophenoxy) benzoate as a colorless oil (1.21 g).

(2) The compound (1.21 g) obtained in (1) was dissolved in THF (18 mL) and MeOH (6 mL), 1.0 M aqueous LiOH solution (12 mL) was added, and the mixture was stirred at room temperature for 30 min. Stir at 0 ° C. for 1 hour. To the reaction solution was added 10% aqueous citric acid solution (60 mL) and AcOEt (30 mL). After separating the two layers, the aqueous layer was extracted with AcOEt (20 mL). The organic layers were combined, and water and saturated brine After washing with water and drying (Na ₂ SO ₄ ), the solvent was distilled off under reduced pressure. The obtained powder was dissolved by heating in AcOEt (10 mL), n-hexane (10 mL) was added under ice cooling, and the mixture was stirred at the same temperature for 1 hour. The precipitate was collected by filtration, and 4- (2,4-
A white powder (456 mg) of dichlorophenoxy) benzoic acid was obtained.
¹ H-NMR (CDCl ₃ , 400 MHz) δ (ppm); 6.91-6.98 (2H, m), 7.06 (1H, d, J = 8.8 Hz), 7.28 (1H, d, J = 8.8, 2.4 Hz) , 7.51 (1H, d, J = 2.4 Hz), 8.05-8.11 (2H, m).

(3) The compound (300 mg) obtained in (2) was dissolved in DMF (3 mL), CDI (190 mg) was added, and the mixture was stirred at room temperature for 1 hour. Octane-1-sulfonamide (226 mg) and DBU (0.17 mL) were added, and the mixture was stirred at room temperature for 13 hours. 10% aqueous citric acid solution (20 mL) and AcOEt (20 mL) were added to the reaction mixture, and the organic layer was separated. The aqueous layer was extracted with AcOEt (20 mL). The organic layers were combined, and water and saturated brine After washing with water and drying (Na ₂ SO ₄ ), the solvent was distilled off under reduced pressure. The obtained residue was purified by column chromatography, the solvent of the target fraction was evaporated under reduced pressure, n-hexane was added to the obtained residue, and the mixture was collected by filtration to give the title compound as a white powder (310 mg). It was.
IRν (ATR) cm ^-1 ; 1678, 1608
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.83 (3H, t, J = 7.1 Hz), 1.10-1.32 (8H, m), 1.30-1.48 (2H, m), 1.59- 1.78 (2H, m), 3.49 (2H, t, J = 7.8 Hz), 6.89-7.08 (2H, m), 7.33 (1H, d, J = 8.8 Hz), 7.52 (1H, d, J = 8.8, 2.4 Hz), 7.85 (1H, d, J = 2.4 Hz), 7.93-8.05 (2H, m), 11.95-12.13 (1H, br).

Example 42
2,4-Dichloro-N- [4- (4-phenylethynylbenzyloxymethyl) benzoyl] benzenesulfonamide sodium salt

(1) 4-Iodobenzyl alcohol (2.70 g, 11.5 mmol) is dissolved in THF (30 mL), and ethynylbenzene (1.77 g), CuI (108 mg, 0.567 mmol), PdCl ₂ (PPh ₃ ) ₂ (400 mg) and Et ₃ N (3.2 mL) were added, and the mixture was stirred at room temperature for 14 hours under an argon atmosphere. Water and AcOEt were added, the two layers were separated, and the organic layer was washed successively with 10% aqueous citric acid solution and saturated brine, and dried (Na ₂ SO ₄ ). The solvent was distilled off under reduced pressure, and the resulting residue was purified by column chromatography. Then, the solvent of the target fraction was distilled off under reduced pressure to obtain (4-phenylethynylphenyl) methanol yellow powder (2.12 g). It was.
¹ H-NMR (CDCl ₃ , 400 MHz) δ (ppm); 1.67 (1H, s), 4.72 (2H, s), 7.32-7.38 (5H, m), 7.50-7.56 (4H, m).

(2) Dissolve the compound (1.20 g) obtained in (1) and methyl 4-bromomethylbenzoate (1.32 g) in toluene (20 mL), add Ag ₂ O (4.00 g), and under argon atmosphere The mixture was stirred at 60 ° C. for 2 hours. Insolubles were filtered off, and the solvent of the filtrate was distilled off under reduced pressure. The obtained residue was purified by column chromatography, and the solvent of the target fraction was evaporated under reduced pressure to obtain white powder (250 mg) of methyl 4- (4-phenylethynylbenzyloxymethyl) benzoate.
¹ H-NMR (CDCl ₃ , 400 MHz) δ (ppm); 3.91 (3H, s), 4.58 (2H, s), 4.61 (2H, s), 7.32-7.38 (5H, m), 7.40-7.45 ( 2H, m), 7.50-7.56 (4H, m), 8.00-8.05 (2H, m).

(3) Dissolve the compound (250 mg) obtained in (2) in MeOH-THF (1: 1) (4 mL), add 1.0 M LiOH aqueous solution (3.4 mL), and stir at 60 ° C. for 2 hours. did. After cooling, neutralized with 1 M hydrochloric acid, the solvent was evaporated under reduced pressure, water was added to the resulting residue, the precipitate was filtered off, and 4- (4-phenylethynylbenzyloxymethyl) benzoic acid Of white powder (200 mg) was obtained.
¹ H-NMR (CDCl ₃ + CD ₃ OD, 400 MHz) δ (ppm); 4.59 (2H, s), 4.63 (2H, s), 7.32-7.38 (5H, m), 7.42-7.47 (2H, m) , 7.50-7.56 (4H, m), 8.01-8.06 (2H, m).

(4) The compound (195 mg) obtained in (3) was dissolved in DMF (3 mL), CDI (102 mg) was added, and the mixture was stirred at room temperature for 0.5 hour, and then 2,4-dichlorobenzenesulfonamide ( 142 mg) and DBU (0.08 mL) were added, and the mixture was stirred at room temperature for 14 hours. Water and AcOEt were added, the two layers were separated, the organic layer was washed with saturated brine, dried (Na ₂ SO ₄ ), and the solvent was evaporated under reduced pressure. The obtained residue was dissolved in MeOH-THF (1: 2) (3 mL), MeONa (31 mg) was added under ice cooling, and the mixture was stirred at room temperature for 1 hr. Et ₂ O was added, insolubles were filtered off, the filtrate was concentrated, and n-hexane was added. The precipitate was collected by filtration to give the title compound as a white powder (133 mg).
IRν (ATR) cm ^-1 ; 1591
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 4.55 (4H, s), 7.27-7.32 (2H, m), 7.38-7.44 (5H, m), 7.46 (1H, dd, J = 8.3, 2.2 Hz), 7.51 (1H, d, J = 2.2 Hz), 7.52-7.58 (4H, m), 7.85-7.90 (2H, m), 7.98 (1H, d, J = 8.3 Hz).

Example 43
N- (2,4-Dichlorobenzoyl) -4- [2- (4-isopropylphenyl) ethoxy] benzenesulfonamide sodium salt

(1) 2- (4-Isopropylphenyl) ethyl methanesulfonate (770 mg) is dissolved in DMF (8 mL), 4-hydroxybenzenesulfonamide (551 mg) and K ₂ CO ₃ (879 mg) are added, Stir at 80 ° C. for 6 hours and at room temperature for 6 hours. Water (20 mL) and AcOEt (20 mL) were added to the reaction mixture, and the organic layer was separated. The aqueous layer was extracted with AcOEt (20 mL). The organic layers were combined, and water (50 mL) and saturated brine were used. Sequential washing and drying (Na ₂ SO ₄ ) were performed. The solvent was distilled off under reduced pressure, and the resulting residue was purified by column chromatography. The solvent of the target fraction was distilled off under reduced pressure to give colorless 4- [2- (4-isopropylphenyl) ethoxy] benzenesulfonamide. An oil (820 mg) was obtained.
¹ H-NMR (CDCl ₃ , 400 MHz) δ (ppm); 1.25 (6H, d, J = 6.8 Hz), 2.83-2.96 (1H, m), 3.09 (2H, t, J = 7.1 Hz), 4.21 (2H, t, J = 7.1 Hz), 4.66-4.75 (2H, br), 6.92-6.98 (2H, m), 7.15-7.22 (4H, m), 7.80-7.87 (2H, m).

(2) 2,4-Dichlorobenzoic acid (193 mg) was dissolved in DMF (3 mL), CDI (180 mg) was added, and the mixture was stirred at room temperature for 1 hour. The compound obtained in (1) (323 mg) and DBU (0.17 mL) were added, and the mixture was stirred at room temperature for 14 hours. 10% aqueous citric acid solution (20 mL) and AcOEt (20 mL) were added to the reaction mixture, and the organic layer was separated. The aqueous layer was extracted with AcOEt (10 mL). After sequential washing and drying (Na ₂ SO ₄ ), the solvent was distilled off under reduced pressure. The obtained residue was purified by column chromatography, and the solvent of the target fraction was distilled off under reduced pressure. The obtained colorless oil was dissolved in THF (5 mL), 5.0 M MeONa-MeOH (0.2 mL) was added under ice cooling, and the mixture was stirred at the same temperature for 15 min. Et ₂ O (30 mL) and n-hexane (3 mL) were added to the reaction solution, and the solvent was distilled off under reduced pressure. The obtained residue was dissolved in MeOH (2 mL), Et ₂ O (3 mL) and n-hexane (50 mL) were added under ice cooling, and the mixture was stirred at the same temperature for 30 min. The precipitate was collected by filtration to give the title compound as a white powder (60 mg).
IRν (ATR) cm ^-1 ; 1581
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 1.17 (6H, d, J = 6.8 Hz), 2.77-2.90 (1H, m), 2.98 (2H, t, J = 6.6 Hz) , 4.19 (2H, t, J = 7.1 Hz), 6.86-6.97 (2H, m), 7.12-7.25 (4H, m), 7.28 (1H, d, J = 8.3 Hz), 7.38-7.47 (2H, m ), 7.65-7.78 (2H, m).

Example 44
N- {4 '-(4-Isopropylphenoxy) biphenyl-4-carbonyl} octane-1-sulfonamide

(1) Methyl 4′-hydroxybiphenyl-4-carboxylic acid (2.15 g) was dissolved in CH ₂ Cl ₂ (43 mL), and 4-isopropylphenylboronic acid (2.32 g), Cu (OAc) ₂ (2.57 g ), Crushed 4A molecular sieves (1.10 g) and pyridine (3.81 mL) were added, and the mixture was stirred at 35 ° C. for 4 hours in an oxygen atmosphere. A 10% aqueous citric acid solution (50 mL) and AcOEt (130 mL) were added to the reaction solution, and the two layers were separated. The aqueous layer was extracted with AcOEt (30 mL), the organic layers were combined, washed with saturated brine, dried (Na ₂ SO ₄ ), and the solvent was evaporated under reduced pressure. The obtained residue was purified by column chromatography, and the solvent of the target fraction was distilled off under reduced pressure to obtain white powder (3.80 g) of methyl 4 ′-(4-isopropylphenoxy) biphenyl-4-carboxylate. .
¹ H-NMR (CDCl ₃ , 400 MHz) δ (ppm); 1.26 (6H, d, J = 7.1 Hz), 2.85-2.98 (1H, m), 3.93 (3H, s), 6.96-7.01 (2H, m), 7.03-7.10 (2H, m), 7.19-7.24 (2H, m), 7.53-7.60 (2H, m), 7.60-7.65 (2H, m), 8.06-8.12 (2H, m).

(2) The compound (3.80 g) obtained in (1) was dissolved in THF (57 mL) and MeOH (19 mL), 1.0 M LiOH aqueous solution (33.0 mL) was added, and the mixture was stirred at room temperature for 45 minutes. A 10% aqueous citric acid solution (200 mL) and AcOEt (100 mL) were added to the reaction solution, and the two layers were separated. The aqueous layer was extracted with AcOEt (50 mL), and the organic layers were combined, washed successively with water and saturated brine, and dried (Na ₂ SO ₄ ). The solvent was distilled off under reduced pressure to obtain 4 ′-(4-isopropylphenoxy) biphenyl-4-carboxylic acid white powder (1.98 g).
¹ H-NMR (CDCl ₃ , 400 MHz) δ (ppm); 1.27 (6H, d, J = 6.8 Hz), 2.85-2.99 (1H, m), 6.87-7.03 (2H, m), 7.06-7.11 ( 2H, m), 7.19-7.25 (2H, m), 7.57-7.62 (2H, m), 7.65-7.70 (2H, m), 8.12-8.20 (2H, m).

(3) The compound (500 mg) obtained in (2) was dissolved in DMF (5 mL), CDI (268 mg) was added, and the mixture was stirred at room temperature for 1 hour. Octane-1-sulfonamide (319 mg) and DBU (0.25 mL) were added, and the mixture was stirred at room temperature for 13 hours and then at 60 ° C. for 6 hours. A 10% aqueous citric acid solution (30 mL) and AcOEt (30 mL) were added to the reaction solution, the organic layer was separated, and the aqueous layer was extracted with AcOEt (30 mL). The organic layers were combined, washed successively with water and saturated brine, dried (Na ₂ SO ₄ ), and the solvent was evaporated under reduced pressure. The obtained residue was purified by column chromatography, and the solvent of the target fraction was distilled off under reduced pressure. N-Hexane was added to the obtained residue, and the mixture was collected by filtration to give the title compound as a white powder (300 mg).
IRν (ATR) cm ^-1 ; 1678
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.83 (3H, t, J = 7.3 Hz), 1.15-1.32 (14H, m), 1.33-1.48 (2H, m), 1.65- 1.79 (2H, m), 2.84-2.99 (1H, m), 3.52 (2H, t, J = 7.3 Hz), 6.97-7.05 (2H, m), 7.03-7.12 (2H, m), 7.25-7.35 ( 2H, m), 7.72-7.85 (4H, m), 7.97-8.07 (2H, m), 11.97-12.18 (1H, br).

Example 45
N- [4 '-(2,4-Dichlorophenoxy) biphenyl-4-carbonyl] octane-1-sulfonamide

(1) Dissolve 2,4-dichlorophenol (2.0 g) in CH ₂ Cl ₂ (40 mL) and add 4-bromophenylboronic acid (2.96 g), Cu (OAc) ₂ (2.67 g), 4A molecular sieves (600 mg) and Et ₃ N (8.57 mL) were added, and the mixture was stirred at 40 ° C. for 2 hours under an oxygen atmosphere. AcOEt and 10% aqueous citric acid solution were added, the insoluble material was filtered, and the two layers were separated. The aqueous layer was extracted twice with AcOEt, the organic layers were combined, washed with saturated brine, dried (Na ₂ SO ₄ ), the solvent was evaporated under reduced pressure, and the resulting residue was purified by column chromatography. Purified. The solvent of the objective fraction was distilled off under reduced pressure to obtain 2,4-dichlorobenzene 4′-bromobenzene ether colorless oil (620 mg).

(2) The compound (620 mg) obtained in (1) was dissolved in 1,4-dioxane (8.3 mL), and 4-methoxycarbonylphenylboronic acid (386 mg), K ₂ CO ₃ (809 mg) A water (4.2 mL) solution and Pd (PPh ₃ ) ₄ (451 mg) were added, and the mixture was stirred at 80 ° C. for 12 hours under a nitrogen atmosphere. After allowing to cool, AcOEt and water were added, and the organic layer was washed with saturated brine and dried (Na ₂ SO ₄ ). The solvent was distilled off under reduced pressure, and the resulting residue was purified by column chromatography. The solvent of the objective fraction was distilled off under reduced pressure to obtain a white powder (270 mg) of methyl 4 ′-(2,4-dichlorophenoxy) biphenyl-4-carboxylate.
¹ H-NMR (CDCl ₃ , 400 MHz) δ (ppm); 3.93 (3H, s), 6.99 (1H, d, J = 8.8 Hz), 7.01-7.04 (2H, m), 7.23 (1H, d, J = 8.8, 2.4 Hz), 7.49 (1H, dd, J = 2.4 Hz), 7.58-7.63 (4H, m), 8.08-8.10 (2H, m).

(3) The compound (270 mg) obtained in (2) is dissolved in MeOH-THF (1: 3) (5.2 mL), 1 M LiOH aqueous solution (2.17 mL) is added, and at room temperature for 30 minutes, and Stir at 50 ° C. for 30 minutes. To the reaction solution was added 10% aqueous citric acid solution (30 mL) and AcOEt (30 mL), the aqueous layer was extracted with AcOEt (30 mL), the organic layers were combined, washed successively with water and saturated brine, and dried. (Na ₂ SO ₄ ). The solvent was distilled off under reduced pressure to obtain a white powder (244 mg) of 4 ′-(2,4-dichlorophenoxy) biphenyl-4-carboxylic acid.
¹ H-NMR (CDCl ₃ , 400 MHz) δ (ppm); 7.00 (1H, d, J = 8.8 Hz), 7.02-7.05 (2H, m), 7.24 (1H, d, J = 8.8, 2.4 Hz) , 7.50 (1H, dd, J = 2.4 Hz), 7.64-7.67 (2H, m), 7.59-7.63 (2H, m), 8.14-8.17 (2H, m).

(4) The compound (240 mg) obtained in (3) was dissolved in DMF (2.4 mL), CDI (119 mg) was added, and the mixture was stirred at room temperature for 1 hour. Octane-1-sulfonamide (142 mg) and DBU (0.11 mL) were added, and the mixture was stirred at room temperature for 14 hours. A 10% aqueous citric acid solution (20 mL) and AcOEt (20 mL) were added to the reaction mixture, the aqueous layer was extracted with AcOEt (20 mL), the organic layers were combined, washed successively with water and saturated brine, and dried ( After Na ₂ SO ₄ ), the solvent was distilled off under reduced pressure. The obtained residue was purified by column chromatography, and the solvent of the target fraction was distilled off under reduced pressure to obtain a white powder. The obtained powder was dissolved in AcOEt (1 mL) with heating, and n-hexane (3 mL) was added under ice cooling, followed by stirring at the same temperature for 1 hour. The precipitate was collected by filtration to give the title compound as a white powder (55 mg).
IRν (ATR) cm ^-1 ; 1693, 1330, 1157
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.83 (3H, t, J = 6.6 Hz), 1.21-1.23 (8H, m), 1.37-1.41 (2H, m), 1.67- 1.74 (2H, m), 7.07-7.10 (2H, m), 7.23 (1H, d, J = 8.8 Hz), 7.48 (1H, dd, J = 8.8, 2.7 Hz), 7.76-7.82 (5H, m) , 8.00-8.02 (2H, m), 12.00-12.09 (1H, br).

Example 46
N- [4- (Biphenyl-4-ylmethoxymethyl) benzoyl] -2,4-dichlorobenzenesulfonamide

(1) Dissolve biphenyl-4-ylmethanol (1.61 g) in THF (20 mL), add 4-bromomethylbenzoic acid (1.00 g), and partition NaH (60%) (874 mg) under ice-cooling. The mixture was added and stirred at room temperature for 16 hours. Under ice-cooling, 2 M aqueous NaOH (10.9 mL) was added dropwise to the reaction mixture, MeOH (3 mL) was added, and the mixture was stirred at 50 ° C. for 1 hr. After allowing to cool, water (30 mL) was added and the mixture was washed with Et ₂ O (30 mL), and the aqueous layer was adjusted to pH 3 with 10% aqueous citric acid solution. The mixture was extracted with AcOEt, washed successively with water and saturated brine, dried (Na ₂ SO ₄ ), and the solvent was evaporated under reduced pressure. The obtained residue was dissolved in AcOEt (20 mL) with heating, n-hexane (20 mL) was added under ice-cooling, and the mixture was stirred at the same temperature for 1 hr. The precipitated crystals were collected by filtration to give 4- (biphenyl-4-ylmethoxymethyl) benzoic acid white powder (850 mg).
¹ H-NMR (CDCl ₃ , 400 MHz) δ (ppm); 4.64 (2H, m), 4.67 (2H, m), 7.31-7.39 (1H, m), 7.40-7.63 (10H, m), 8.08- 8.15 (2H, m).

(2) The compound (410 mg) obtained in (1) was dissolved in DMF (4 mL), CDI (230 mg) was added, and the mixture was stirred at room temperature for 1 hour. 2,4-Dichlorobenzenesulfonamide (321 mg) and DBU (0.21 mL) were added, and the mixture was stirred at room temperature for 15 hours. A 10% aqueous citric acid solution (20 mL) and AcOEt (20 mL) were added to the reaction solution, the organic layer was separated, and the aqueous layer was extracted with AcOEt (10 mL). The organic layers were combined, washed successively with water and saturated brine, dried (Na ₂ SO ₄ ), and the solvent was evaporated under reduced pressure. The resulting pale yellow oil was dissolved in Et ₂ O (7 mL) and stirred at room temperature for 30 minutes and under ice-cooling for 30 minutes. The precipitate was collected by filtration to give the title compound as a white powder (470 mg).
IRν (ATR) cm ^-1 ; 1610, 1693
¹ H-NMR (CDCl ₃ , 400 MHz) δ (ppm); 4.56-4.65 (4H, m), 7.31-7.55 (9H, m), 7.55-7.63 (4H, m), 7.76-7.83 (2H, m ), 8.31 (1H, d, J = 8.6 Hz), 8.80-9.50 (1H, br).

Example 47
N- [4- (Biphenyl-4-ylmethyl) benzoyl] naphthalene-2-sulfonamide

(1) 4-Bromobiphenyl (2.84 g) was dissolved in THF (60 mL), and 1.6 M n-butyllithium (n-BuLi) -n-hexane (7.6 mL) was added at -78 ° C under a nitrogen atmosphere. After dropwise addition and stirring at the same temperature for 1 hour, a solution of methyl 4-formylbenzoate (2.00 g) in THF (30 mL) was added, and the mixture was stirred for 30 minutes while warming to room temperature. Saturated aqueous ammonium chloride was added to the reaction mixture, and the mixture was extracted with AcOEt. The organic layer was washed with saturated brine, dried (Na ₂ SO ₄ ), and the solvent was evaporated under reduced pressure. The obtained residue was purified by column chromatography, and the solvent of the target fraction was distilled off under reduced pressure to obtain white powder (960 mg) of methyl 4-[(biphenyl-4-yl) hydroxymethyl] benzoate. .
¹ H-NMR (CDCl ₃ , 400 MHz) δ (ppm); 2.40 (1H, d, J = 3.2 Hz), 3.90 (3H, s), 5.92 (1H, d, J = 3.2 Hz), 7.30-7.37 (1H, m), 7.38-7.46 (4H, m), 7.48-7.53 (2H, m), 7.53-7.60 (4H, m), 7.98-8.05 (2H, m).

(2) Dissolve the compound (960 mg) obtained in (1) in trifluoroacetic acid (TFA) (4.6 mL), add triethylsilane (Et ₃ SiH) (2.39 mL) at room temperature, and heat for 15 minutes. Refluxed. After allowing to cool, water was added to the reaction mixture, and the mixture was extracted with CHCl ₃ . The organic layer was dried (Na ₂ SO ₄ ), the solvent was distilled off under reduced pressure, n-hexane was added to the resulting residue, the insoluble material was collected by filtration, and methyl 4-biphenyl-4-ylmethylbenzoate white A powder (851 mg) was obtained. The obtained powder (850 mg) was suspended in MeOH (10 mL), 5.0 M NaOH aqueous solution (1.7 mL) was added, and the mixture was stirred at 40 ° C. for 30 min. The reaction solution was washed with AcOEt, acidified with 6.0 M hydrochloric acid, and extracted with AcOEt. The organic layer was washed with saturated brine, dried (Na ₂ SO ₄ ), and the solvent was evaporated under reduced pressure to give 4- (biphenyl-4-ylmethyl) benzoic acid as a white powder (416 mg).
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 4.05 (2H, s), 7.30-7.48 (7H, m), 7.55-7.66 (4H, m), 7.83-7.92 (2H, m ), 12.7-12.9 (1H, br).

(3) The compound (370 mg) obtained in (2) was dissolved in DMF (3 mL), CDI (280 mg) was added, and after stirring at room temperature for 1 hour, naphthalene-2-sulfonamide (240 mg ) And DBU (0.34 mL) were added, and the mixture was stirred at 80 ° C. for 2 hours. To the reaction solution was added an aqueous citric acid solution, and the mixture was extracted with AcOEt. The organic layer was washed successively with water and saturated brine, dried (Na ₂ SO ₄ ), and the solvent was evaporated under reduced pressure. The obtained residue was purified by column chromatography, and the solvent of the target fraction was distilled off under reduced pressure. To the obtained residue was added tert-butyl methyl ether (t-BuOMe) (10 mL), and the precipitate was collected by filtration to give the title compound as a white powder (246 mg).
IRν (ATR) cm ^-1 ; 1428, 1344
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 4.02 (2H, s), 7.25-7.47 (7H, m), 7.52-7.64 (4H, m), 7.65-7.83 (4H, m ), 7.93 (1H, dd, J = 8.8, 1.7 Hz), 8.04 (1H, d, J = 8.0 Hz), 8.13 (1H, d, J = 8.8 Hz), 8.22 (1H, dd, J = 7.8 Hz) ), 8.66 (1H, s), 12.45-12.65 (1H, br).

Example 48
N- [4- (4-Isopropylbenzoyl) benzoyl] octane-1-sulfonamide

(1) Methyl 4- [hydroxy (4-isopropylphenyl) methyl] benzoate (840 mg) synthesized according to (1) of Example 47 was dissolved in CH ₂ Cl ₂ (4.5 mL), and pyridinium chlorochromate was dissolved. (1.27 g) was added and stirred at room temperature for 2 hours. CH ₂ Cl ₂ was added, washed successively with water and then with saturated brine, and dried (Na ₂ SO ₄ ). After evaporating the solvent under reduced pressure and purifying the resulting residue by column chromatography, the solvent of the target fraction was evaporated under reduced pressure to give methyl 4- (4-isopropylbenzoyl) benzoate as an oil (770 mg) Got. The obtained oil (770 mg) was dissolved in a mixed solution (20 mL) of THF-MeOH (3: 1), 2.0 M LiOH aqueous solution (5 mL) was added, and the mixture was stirred at room temperature for 1.5 hours. A 10% aqueous citric acid solution was added to the reaction solution, and the mixture was extracted with AcOEt. The organic layer was washed with saturated brine, dried (Na ₂ SO ₄ ), and the solvent was evaporated under reduced pressure to give 4- (4-isopropylbenzoyl) benzoic acid white powder (260 mg).

(2) The compound (255 mg) obtained in (1) was dissolved in DMF (2.6 mL), CDI (230 mg) was added, and after stirring at room temperature for 30 minutes, octane-1-sulfonamide (240 mg ) And DBU (220 mg) were added, and the mixture was stirred at room temperature for 15 hours. To the reaction solution was added an aqueous citric acid solution, and the mixture was extracted with AcOEt. The organic layer was washed successively with water and saturated brine, dried (Na ₂ SO ₄ ), and the solvent was evaporated under reduced pressure. The obtained residue was purified by column chromatography, and the solvent of the target fraction was distilled off under reduced pressure. Et ₂ O was added to the obtained residue, and the precipitate was collected by filtration to give the title compound as a white powder (260 mg).
IRν (ATR) cm ^-1 ; 1699, 1647, 1606
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.84 (3H, t, J = 6.8 Hz), 1.18-1.31 (8H, m), 1.25 (6H, d, J = 6.8 Hz) , 1.35-1.45 (2H, m), 1.66-1.75 (2H, m), 3.01 (1H, quintet, J = 6.8 Hz), 3.49-3.58 (2H, m), 7.43-7.48 (2H, m), 7.67 -7.72 (2H, m), 7.79-7.84 (2H, m), 8.05-8.09 (2H, m), 12.00-12.50 (1H, br).

Example 49
N- {4- [2- (biphenyl-4-yl) acetylaminomethyl] benzoyl} octane-1-sulfonamide

(1) Biphenyl-4-ylacetic acid (1.00 g) and methyl 4-aminomethylbenzoate (950 mg) were suspended in CH ₂ Cl ₂ (15 mL), and EDC (1.17 g) and Et ₃ N were suspended under ice cooling. (0.72 mL) was added, and the mixture was stirred at room temperature for 15 hours. To the reaction solution was added 10% aqueous citric acid solution (20 mL), the precipitate was collected by filtration, washed with water and CH ₂ Cl ₂ , and methyl 4-[(2- (biphenyl-4-yl) acetylaminomethyl. A white powder of benzoate (1.32 g) was obtained.
¹ H-NMR (CDCl ₃ , 400 MHz) δ (ppm); 3.55 (2H, s), 3.83 (3H, s), 4.36 (2H, d, J = 5.9 Hz), 7.30-7.41 (5H, m) , 7.42-7.49 (2H, m), 7.57-7.67 (4H, m), 7.87-7.93 (2H, m), 8.67 (1H, t, J = 5.9 Hz).

(2) The compound (1.32 g) obtained in (1) was suspended in THF (20 mL) and MeOH (6.6 mL), 1.0 M LiOH aqueous solution (11.0 mL) was added, and the mixture was heated to reflux for 4 hours. To the reaction mixture was added 3 M hydrochloric acid (200 mL) and AcOEt (500 mL), and the insoluble material was collected by filtration. 4-[(2- (biphenyl-4-yl) acetylaminomethyl] benzoic acid white powder (800 mg).
¹ H-NMR (CDCl ₃ , 400 MHz) δ (ppm); 3.54 (2H, s), 4.35 (2H, d, J = 5.9 Hz), 7.30-7.40 (5H, m), 7.40-7.50 (2H, m), 7.57-7.71 (4H, m), 7.86-7.92 (2H, m), 8.66 (1H, t, J = 5.9 Hz), 12.58-13.20 (1H, br).

(3) The compound (490 mg) obtained in (2) was suspended in DMF (10 mL), CDI (253 mg) was added, and the mixture was stirred at room temperature for 1 hour. Octane-1-sulfonamide (302 mg) and DBU (0.23 mL) were added, and the mixture was stirred at room temperature for 14 hours. A 10% aqueous citric acid solution (30 mL) and AcOEt (30 mL) were added to the reaction mixture, and the precipitate was collected by filtration to give a white powder. The obtained powder was washed with CHCl ₃ and the filtrate was distilled off under reduced pressure. CHCl ₃ (3 mL) and MeOH (1 mL) were added to the obtained residue, dissolved by heating, Et ₂ O (25 mL) was added under ice cooling, and the mixture was stirred at the same temperature for 30 min. The precipitate was collected by filtration to give the title compound as a white powder (40 mg).
IRν (ATR) cm ^-1 ; 1678, 1631
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.83 (3H, t, J = 6.8 Hz), 1.14-1.30 (8H, m), 1.31-1.47 (2H, m), 1.60- 1.75 (2H, m), 3.36-3.58 (2H, m), 3.54 (2H, s), 4.35 (2H, d, J = 5.8 Hz), 7.30-7.41 (5H, m), 7.42-7.52 (2H, m), 7.56-7.71 (4H, m), 7.83-7.93 (2H, m), 8.60-8.73 (1H, m), 11.90-12.10 (1H, br).

Example 50
N- [4- (Biphenyl-4-ylmethoxymethyl) benzoyl] -9H-fluorene-2-sulfonamide

(1) 9H-fluoren-2-ylamine (3.0 g) was dissolved in acetonitrile (MeCN) (38 mL), concentrated hydrochloric acid (27 mL) was added at -5 ° C, and the mixture was stirred for 10 minutes, and then CuCl ₂ (1.12 An aqueous solution (3.8 mL) of g) was added dropwise and stirred for 5 minutes. An aqueous solution (3.8 mL) of 30% SO ₂ -AcOH (42.5 mL) and CuCl ₂ (1.12 g) was added dropwise, and the mixture was stirred at room temperature for 45 hours. Water was added to the reaction solution, followed by extraction twice with AcOEt, and the organic layer was washed successively with water and saturated brine and dried (Na ₂ SO ₄ ). The solvent was distilled off under reduced pressure to obtain a crude product (9.8 g) of 9H-fluorene-2-sulfonyl chloride. The obtained 9H-fluorene-2-sulfonyl chloride (4.39 g) was dissolved in THF (40 mL), 28% aqueous ammonia (7.1 mL) was added, and the mixture was stirred at room temperature for 10 min. AcOEt was added to the reaction solution, washed successively with 10% aqueous citric acid solution, water and saturated brine, dried (Na ₂ SO ₄ ), and the solvent was evaporated under reduced pressure. Et ₂ O (50 mL) was added to the resulting residue, stirred for 10 minutes, and then collected by filtration to obtain a light brown powder (2.47 g) of 9H-fluorene-2-sulfonamide.
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 4.04 (2H, s), 7.32-7.36 (2H, br), 7.37-7.46 (2H, m), 7.63-7.65 (1H, m ), 7.84-7.88 (1H, m), 7.98-8.01 (1H, m), 8.02-8.03 (1H, m), 8.06-8.09 (1H, m).

(2) The compound (500 mg) obtained in Example 46 (1) was dissolved in DMF (5 mL), CDI (281 mg) was added, and the mixture was stirred at room temperature for 1 hour. The compound obtained in (1) (424 mg) and DBU (0.26 mL) were added, and the mixture was stirred at room temperature for 14 hours and then stirred at 50 ° C. for 1 hour. After allowing to cool, 10% aqueous citric acid solution (30 mL) and AcOEt (30 mL) were added to the reaction mixture, the organic layer was separated, the aqueous layer was extracted with AcOEt (30 mL), the organic layers were combined, After sequentially washing with saturated brine and drying (Na ₂ SO ₄ ), the solvent was distilled off under reduced pressure. The obtained residue was purified by column chromatography, and the solvent of the target fraction was distilled off under reduced pressure. Et ₂ O (5 mL) was added to the obtained residue, and the mixture was stirred for 20 min and collected by filtration to give the title compound as a pale yellow powder (295 mg).
IRν (ATR) cm ^-1 ; 1698, 1334, 1151
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 4.08 (2H, s), 4.59 (2H, s), 4.62 (2H, s), 7.33-7.38 (1H, m), 7.40- 7.48 (8H, m), 7.63-7.66 (5H, m), 7.86-7.88 (2H, m), 8.02-8.04 (2H, m), 8.14-8.16 (1H, m), 8.19-8.20 (1H, m ), 12.52-12.60 (1H, br).

Example 51
N- (Dibutylaminosulfonyl) -4- (biphenyl-4-ylmethoxymethyl) benzamide

(1) Chlorosulfonyl isocyanate (1.24 mL) was dissolved in CH ₂ Cl ₂ (10 mL), tert-butyl alcohol (1.35 mL) was added at 0 ° C., and the mixture was stirred at room temperature for 2 hr. The reaction solution was cooled to 0 ° C., dibutylamine (2.38 mL), and then Et ₃ N (2.15 mL) were sequentially added, followed by stirring at room temperature for 14 hours. The reaction mixture was washed successively with 10% aqueous citric acid solution and then with saturated brine, dried (Na ₂ SO ₄ ), and the solvent was evaporated under reduced pressure. Trifluoroacetic acid (5.0 mL) was added to the obtained residue, and the mixture was stirred at room temperature for 4 hours. Saturated multistory water was added to the reaction liquid, extracted twice with CHCl ₃ , the organic layers were combined, washed with saturated brine, and dried (Na ₂ SO ₄ ). The solvent was distilled off under reduced pressure to obtain N, N-dibutylsulfamoylamine (2.63 g).
¹ H-NMR (CDCl ₃ , 400 MHz) δ (ppm); 0.94 (6H, t, J = 7.4 Hz), 1.28-1.39 (4H, m), 1.53-1.63 (4H, m), 3.12-3.19 ( 4H, m), 4.45-4.70 (2H, br).

(2) The compound (478 mg) obtained in (1) of Example 46 was dissolved in DMF (5 mL), CDI (365 mg) was added, and the mixture was stirred at room temperature for 0.5 hour and then obtained in (1). The obtained compound (625 mg) and DBU (0.671 mL) were added, and the mixture was stirred at 80 ° C. for 3 hr. A 5% aqueous citric acid solution was added to the reaction solution, and the mixture was extracted twice with AcOEt. The organic layer was washed successively with water and saturated brine, dried (Na ₂ SO ₄ ), and the solvent was evaporated under reduced pressure. The obtained residue was purified by column chromatography, and the solvent of the target fraction was evaporated under reduced pressure to give the title compound as a pale yellow oil (540 mg).
IRν (ATR) cm ^-1 ; 1679
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.86 (6H, t, J = 7.6 Hz), 1.20-1.33 (4H, m), 1.45-1.55 (4H, m), 3.26- 3.33 (4H, m), 4.61 (2H, s), 4.64 (2H, s), 7.32-7.39 (1H, m), 7.43-7.52 (6H, m), 7.63-7.69 (4H, m), 7.86- 7.92 (2H, m), 11.85 (1H, s).

Example 52
N- [4- (4-Isopropylbenzyloxymethyl) phenyl] -N '-(octane-1-sulfonyl) urea diphenylphosphoric acid azide (DPPA) (550 mg) was dissolved in toluene (5 mL) and 4- (4-Isopropylbenzyloxymethyl) benzoic acid (569 mg) and Et ₃ N (0.31 mL) were added, and the mixture was stirred at 100 ° C. for 15 min. To a solution of octane-1-sulfonamide (580 mg) and DBU (0.45 mL) in DMF (5 mL), the previous solution was added dropwise at 100 ° C., and the mixture was further stirred at the same temperature for 15 minutes. A 5% aqueous citric acid solution was added to the reaction solution, and the mixture was extracted twice with AcOEt. The organic layer was washed successively with water and saturated brine, dried (Na ₂ SO ₄ ), the solvent was distilled off under reduced pressure, and the resulting residue was purified by column chromatography. Distilled off under reduced pressure. T-BuOMe was added to the obtained residue, and the mixture was collected by filtration to give the title compound as a white powder (173 mg).
IRν (ATR) cm ^-1 ; 1650
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.80-0.86 (3H, m), 1.15-1.32 (14H, m), 1.34-1.45 (2H, m), 1.65-1.75 (2H , m), 2.82-2.94 (1H, m), 3.38-3.48 (2H, m), 4.45 (4H, s), 7.18-7.31 (6H, m), 7.36-7.43 (2H, m), 8.81 (1H , s), 10.12-10.30 (1H, br).

Example 53
N- [5- (2,3-Dihydro-1H-indol-1-ylmethyl) benzofuran-2-carbonyl] octane-1-sulfonamide

(1) 2-hydroxy-5-methylbenzaldehyde (2.72 g) was dissolved in DMF (20 mL), methyl bromoacetate (3.37 g) and potassium carbonate (8.29 g) were added, and the mixture was stirred at 100 ° C. for 16 hours. . A 10% aqueous citric acid solution was added to the reaction solution, and the mixture was extracted with AcOEt. The organic layer was washed with saturated brine and dried (Na ₂ SO ₄ ). The solvent was distilled off under reduced pressure, and the resulting residue was purified by column chromatography to obtain methyl 5-methylbenzofuran-2-carboxylate (1.61 g).
¹ H-NMR (CDCl ₃ , 400 MHz) δ (ppm); 2.45 (3H, s), 3.97 (3H, s), 7.20-7.30 (1H, m), 7.41-7.50 (3H, m).

(2) The compound obtained in (1) was dissolved in carbon tetrachloride (20 mL), N-bromosuccinimide (854 mg) and azobisisobutyronitrile (66 mg) were added, and the mixture was refluxed for 17 hours. The reaction mixture was washed successively with water and then with saturated brine, dried (Na ₂ SO ₄ ), and the solvent was evaporated under reduced pressure. The obtained residue was purified by column chromatography to obtain methyl 5-bromomethylbenzofuran-2-carboxylate (980 mg).
¹ H-NMR (CDCl ₃ , 400 MHz) δ (ppm); 3.98 (3H, s), 4.61 (2H, s), 7.46-7.61 (3H, m), 7.68-7.75 (1H, m).

(3) Dissolve the compound (500 mg) obtained in (2) in DMF (5.0 mL), add 2,3-dihydro-1H-indole (221 mg) and potassium carbonate (511 mg), and bring to room temperature. And stirred for 16 hours. Water was added to the reaction solution, followed by extraction with AcOEt. The organic layer was washed with saturated brine and dried (Na ₂ SO ₄ ). The solvent was distilled off under reduced pressure, and the resulting residue was purified by column chromatography to obtain methyl 5- (2,3-dihydro-1H-indol-1-ylmethyl) benzofuran-2-carboxylate (450 mg). Obtained.
¹ H-NMR (CDCl ₃ , 400 MHz) δ (ppm); 2.99 (2H, t, J = 8.3 Hz), 3.32 (2H, t, J = 8.3 Hz), 3.98 (3H, s), 4.34 (2H , s), 6.48-6.54 (1H, m), 6.65-6.71 (1H, m), 7.02-7.08 (1H, m), 7.08-7.14 (1H, m), 7.46 (1H, dd, J = 8.7, 2.0 Hz), 7.49 (1H, s), 7.55 (1H, d, J = 8.7 Hz), 7.68 (1H, s).

(4) Dissolve the compound (450 mg) obtained in (3) in a THF-MeOH (1: 1) mixture (4.0 mL), add 5.0 M NaOH aqueous solution (1.5 mL), and at room temperature for 2 hours. Stir. 6 M hydrochloric acid (1.5 mL) was added to the reaction mixture, and the mixture was extracted with AcOEt. The organic layer was washed with saturated brine and dried (Na ₂ SO ₄ ). The solvent was distilled off under reduced pressure to obtain 5- (2,3-dihydro-1H-indol-1-ylmethyl) benzofuran-2-carboxylic acid powder (330 mg).
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 2.89 (2H, t, J = 8.3 Hz), 3.27 (2H, t, J = 8.3 Hz), 4.36 (2H, s), 6.55 -6.62 (2H, m), 6.94-7.01 (1H, m), 7.01-7.08 (1H, m), 7.48 (1H, dd, J = 8.5, 1.7 Hz), 7.64 (1H, s), 7.66 (1H , d, J = 8.5 Hz), 7.75 (1H, s).

(5) The compound (320 mg) obtained in (4) was suspended in DMF (5 mL), CDI (230 mg) was added, and the mixture was stirred at room temperature for 30 minutes. Octane-1-sulfonamide (316 mg) and DBU (0.33 mL) were added, and the mixture was stirred at 50 ° C. for 18 hours. A 10% aqueous citric acid solution was added to the reaction solution, followed by extraction with AcOEt. The organic layer was washed with saturated brine and dried (Na ₂ SO ₄ ). The solvent was distilled off under reduced pressure, and the resulting residue was purified by column chromatography, and then the solvent of the target fraction was distilled off under reduced pressure. A mixture of Et ₂ On-hexane (1: 3) was added to the obtained residue, and the mixture was collected by filtration to give the title compound as a white powder (360 mg).
IRν (ATR) cm ^-1 ; 1685, 1606, 1576.
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.87-0.84 (3H, m), 1.14-1.31 (8H, m), 1.31-1.45 (2H, m), 1.62-1.78 (2H , m), 2.89 (2H, t, J = 8.3 Hz), 3.26 (2H, t, J = 8.3 Hz), 3.47-3.57 (2H, m), 4.36 (2H, s), 6.56-6.63 (2H, m), 6.94-7.02 (1H, m), 7.02-7.08 (1H, m), 7.52 (1H, dd, J = 8.8, 1.5 Hz), 7.69 (1H, d, J = 8.8 Hz), 7.80 (1H , s) 7.96 (1H, s), 12.20-12.70 (1H, br).

The compounds of Examples 54 to 190 were produced in the same manner as in Examples 34 to 53.

Example 54
N- [6- (Biphenyl-4-yloxy) benzofuran-2-carbonyl] -2,4-dichlorobenzenesulfonamide sodium salt
IRν (ATR) cm ^-1 ; 1603
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 7.01 (1H, dd, J = 8.5, 2.0 Hz), 7.07-7.14 (2H, m), 7.20 (1H, s), 7.30- 7.71 (11H, m), 7.99 (1H, d, J = 8.5 Hz).

Example 55
N- [6- (Biphenyl-3-yloxy) benzofuran-2-carbonyl] -2,4-dichlorobenzenesulfonamide
IRν (ATR) cm ^-1 ; 1697
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 7.02-7.08 (1H, m), 7.12 (1H, dd, J = 8.6, 2.2 Hz), 7.12-7.17 (1H, m), 7.28-7.33 (1H, m), 7.30-7.50 (6H, m), 7.52-7.58 (5H, m), 7.50-7.52 (1H, m), 7.52-7.58 (2H, m), 7.58 (1H, d , J = 2.0 Hz), 7.62 (1H, d, J = 8.6 Hz), 8.29 (1H, d, J = 8.5 Hz), 8.88-9.21 (1H, br).

Example 56
2,4-Dichloro-N- [6- (4'-fluorobiphenyl-4-yloxy) benzofuran-2-carbonyl] benzenesulfonamide sodium salt
IRν (ATR) cm ^-1 ; 1599
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 7.00 (1H, dd, J = 8.6, 2.0 Hz), 7.06-7.13 (2H, m), 7.21 (1H, s), 7.24- 7.32 (2H, m), 7.30-7.37 (1H, br), 7.49 (1H, dd, J = 8.6, 2.0 Hz), 7.56 (1H, d, J = 2.0 Hz), 7.62-7.74 (5H, m) , 8.00 (1H, d, J = 8.6 Hz).

Example 57
2,4-Dichloro-N- [6- (9H-fluoren-2-yloxy) benzofuran-2-carbonyl] benzenesulfonamide
IRν (ATR) cm ^-1 ; 1610
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 3.83 (2H, s), 6.93 (1H, dd, J = 8.5, 2.2 Hz), 7.01 (1H, dd, J = 8.3, 2.2 Hz), 7.14 (1H, s), 7.17 (1H, d, J = 2.2 Hz), 7.22 (1H, d, J = 2.2 Hz), 7.18-7.32 (2H, m), 7.42 (1H, dd, J = 8.6, 2.0 Hz), 7.46-7.50 (1H, m), 7.50 (1H, d, J = 2.0 Hz), 7.61 (1H, d, J = 8.5 Hz), 7.76-7.80 (1H, m), 7.82 (1H, d, J = 8.3 Hz), 7.93 (1H, d, J = 8.6 Hz).

Example 58
2,4-Dichloro-N- [6- (4'-chlorobiphenyl-4-yloxy) benzofuran-2-carbonyl] benzenesulfonamide
IRν (ATR) cm ^-1 ; 1703
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 7.09 (1H, dd, J = 8.8, 2.2 Hz), 7.12-7.16 (2H, m), 7.35 (1H, d, J = 2.2 Hz), 7.47-7.52 (2H, m), 7.65-7.72 (5H, m), 7.83 (1H, d, J = 8.8 Hz), 7.85 (1H, s), 7.92 (1H, s), 8.14 (1H , d, J = 8.8 Hz).

Example 59
N- [6- (4-Chlorophenoxy) benzofuran-2-carbonyl] -2,4-dichlorobenzenesulfonamide sodium salt
IRν (ATR) cm ^-1 ; 1618
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 6.97 (1H, dd, J = 8.6, 2.2 Hz), 7.01-7.08 (2H, m), 7.17-7.21 (1H, s), 7.28-7.33 (1H, m), 7.38-7.45 (2H, m), 7.48 (1H, dd, J = 8.6, 2.0 Hz), 7.56 (1H, d, J = 2.0 Hz), 7.67 (1H, d, J = 8.6 Hz), 7.99 (1H, d, J = 8.6 Hz).

Example 60
2,4-Dichloro-N- [6- (2,4-dichlorophenoxy) benzofuran-2-carbonyl] benzenesulfonamide
IRν (ATR) cm ^-1 ; 1697, 1255, 1155
¹ H-NMR (CDCl ₃ , 400 MHz) δ (ppm); 7.06 (1H, dd, J = 8.7, 2.1 Hz), 7.19 (1H, d, J = 8.7 Hz), 7.29 (1H, d, J = 2.1 Hz), 7.45 (1H, dd, J = 8.7, 2.4 Hz), 7.72 (1H, dd, J = 8.6, 2.0 Hz), 7.80 (1H, d, J = 2.4 Hz), 7.84 (1H, d, J = 8.7 Hz), 7.88 (1H, d, J = 2.0 Hz), 7.97-8.01 (1H, m), 8.16 (1H, d, J = 8.6 Hz).

Example 61
2,4-Dichloro-N- [2- (4-isopropylphenoxy) -1H-benzimidazol-5-carbonyl] benzenesulfonamide hydrochloride
IRν (ATR) cm ^-1 ; 1697, 1633
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 1.23 (6H, d, J = 7.1 Hz), 2.88-3.00 (1H, m), 7.28-7.39 (4H, m), 7.38- 7.47 (1H, m), 7.65-7.81 (2H, m), 7.87-7.94 (1H, m), 7.99 (1H, d, J = 1.5 Hz), 8.17 (1H, d, J = 8.5 Hz), 12.60 -13.10 (1H, br).

Example 62
2,4-Dichloro-N- [2- (biphenyl-4-yloxy) -1H-benzimidazol-5-carbonyl] benzenesulfonamide hydrochloride
IRν (ATR) cm ^-1 ; 1693, 1626
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 7.35-7.55 (6H, m), 7.66-7.80 (6H, m), 7.90 (1H, d, J = 1.9 Hz), 8.00- 8.04 (1H, m), 8.17 (1H, d, J = 8.6 Hz), 9.80-10.50 (1H, br), 12.62-13.25 (1H, br).

Example 63
2,4-Dichloro-N- [4- (4-isopropylbenzyloxymethyl) benzoyl] benzenesulfonamide sodium salt
IRν (ATR) cm ^-1 ; 1593
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 1.18 (6H, d, J = 6.8 Hz), 2.82-2.92 (1H, m), 4.46 (2H, s), 4.51 (2H, s), 7.18-7.30 (6H, m), 7.82-7.88 (2H, m), 7.45 (1H, dd, J = 8.6, 2.0 Hz), 7.50 (1H, d, J = 2.0 Hz), 7.98 (1H , d, J = 8.6 Hz).

Example 64
N- [4- (4-tert-Butylbenzyloxymethyl) benzoyl] -2,4-dichlorobenzenesulfonamide sodium salt
IRν (ATR) cm ^-1 ; 1595
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 1.27 (9H, s), 4.47 (2H, s), 4.52 (2H, s), 7.24-7.30 (4H, m), 7.35- 7.40 (2H, m), 7.46 (1H, dd, J = 8.4, 2.0 Hz), 7.51 (1H, d, J = 2.0 Hz), 7.83-7.88 (2H, m), 7.98 (1H, d, J = (8.4 Hz).

Example 65
2-Bromo-4-chloro-N- {4- [4- (2-methyl-1-propenyl) benzyloxymethyl] benzoyl} benzenesulfonamide
IRν (ATR) cm ^-1 ; 1689, 1612
¹ H-NMR (CDCl ₃ , 400 MHz) δ (ppm); 1.83-1.93 (6H, m), 4.56 (2H, s), 4.59 (2H, s), 6.22-6.28 (1H, m), 7.18- 7.23 (2H, m), 7.26-7.32 (2H, m), 7.42-7.50 (2H, m), 7.54 (1H, dd, J = 8.6, 2.2 Hz), 7.72 (1H, d, J = 2.2 Hz) , 7.75-7.81 (2H, m), 8.31-8.39 (2H, m), 8.34 (1H, d, J = 8.6 Hz), 9.00-9.10 (1H, br).

Example 66
(E) -2-Bromo-4-chloro-N- {4- [5-methyl-2- (4-methylpent-1-enyl) oxazol-4-ylmethoxymethyl] benzoyl} benzenesulfonamide
IRν (ATR) cm ^-1 ; 1684
¹ H-NMR (CDCl ₃ , 400 MHz) δ (ppm); 0.94 (6H, d, J = 6.6 Hz), 1.70-1.80 (1H, m), 2.09-2.14 (2H, m), 2.30 (3H, s), 4.41 (2H, s), 4.63 (2H, s), 6.20 (1H, d, J = 15.8 Hz), 6.62 (1H, dt, J = 15.8, 7.6 Hz), 7.43-7.48 (2H, m ), 7.54 (1H, dd, J = 9.0, 2.2 Hz), 7.72 (1H, d, J = 2.2 Hz), 7.74-7.79 (2H, m), 8.34 (1H, d, J = 9.0 Hz).

Example 67
2,4-Dichloro-N- [4- (4-isopropoxybenzyloxymethyl) benzoyl] benzenesulfonamide
IRν (ATR) cm ^-1 ; 1689
¹ H-NMR (CDCl ₃ , 400 MHz) δ (ppm); 1.33 (6H, d, J = 6.1 Hz), 4.49 (2H, s), 4.50-4.60 (1H, m), 4.56 (2H, s) , 6.84-6.89 (2H, m), 7.21-7.26 (2H, m), 7.41-7.46 (2H, m), 7.75-7.80 (2H, m), 7.47-7.52 (2H, m), 8.31 (1H, d, J = 8.5 Hz), 9.17 (1H, s).

Example 68
2-Bromo-4-chloro-N- [4- (4-nitrobenzyloxymethyl) benzoyl] benzenesulfonamide
IRν (ATR) cm ^-1 ; 1614
¹ H-NMR (CDCl ₃ , 400 MHz) δ (ppm); 4.66 (2H, s), 4.67 (2H, s), 7.43-7.58 (5H, m), 7.72 (1H, d, J = 1.9 Hz) , 7.78-7.88 (2H, m), 8.31-8.39 (2H, m), 8.35 (1H, d, J = 8.5 Hz), 9.18-9.38 (1H, br).

Example 69
2,4-Dichloro-N- [2-chloro-4- (4-isopropylbenzyloxymethyl) benzoyl] benzenesulfonamide sodium salt
IRν (ATR) cm ^-1 ; 1585
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 1.18 (6H, d, J = 7.1 Hz), 2.80-2.92 (1H, m), 4.46 (2H, s), 4.48 (2H, s), 7.18-7.28 (6H, m), 7.46 (1H, dd, J = 8.5, 2.2 Hz), 7.54 (1H, d, J = 7.6 Hz), 7.56 (1H, d, J = 2.2 Hz), 7.98 (1H, d, J = 8.5 Hz).

Example 70
2,4-Dichloro-N- {4- [2- (4-isopropylphenyl) ethoxy] benzoyl} benzenesulfonamide
IRν (ATR) cm ^-1 ; 1685
¹ H-NMR (CDCl ₃ , 400 MHz) δ (ppm); 1.24 (6H, d, J = 6.8 Hz), 2.82-2.96 (1H, m), 3.07 (2H, t, J = 7.1 Hz), 4.19 (2H, t, J = 7.1 Hz), 6.85-6.95 (2H, m), 7.12-7.28 (4H, m), 7.48 (1H, dd, J = 8.6, 2.0 Hz), 7.50 (1H, d, J = 2.0 Hz), 7.68-7.80 (2H, m), 8.30 (1H, d, J = 8.6 Hz), 8.90-9.15 (1H, br).

Example 71
2,4-Dichloro-N- {4- [4- (furan-2-yl) benzyloxymethyl] benzoyl} benzenesulfonamide sodium salt
IRν (ATR) cm ^-1 ; 1595
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 4.46 (2H, s), 4.48 (2H, s), 6.52 (1H, dd, J = 3.4, 2.0 Hz), 6.87 (1H, d, J = 3.4 Hz), 7.20-7.25 (2H, m), 7.31-7.36 (2H, m), 7.39 (1H, dd, J = 8.3, 2.2 Hz), 7.44 (1H, d, J = 2.2 Hz ), 7.59-7.64 (2H, m), 7.67 (1H, d, J = 2.0 Hz), 7.79-7.84 (2H, m), 7.91 (1H, d, J = 8.3 Hz).

Example 72
N- [4- (2,4-Dichlorobenzyloxymethyl) benzoyl] -5-isopropyl-3,8-dimethylazulene-1-sulfonamide
IRν (ATR) cm ^-1 ; 1707
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 1.30 (6H, d, J = 6.8 Hz), 2.78 (3H, s), 2.82 (3H, s), 3.09-3.18 (1H, m), 4.59 (2H, s), 4.65 (2H, s), 7.24 (1H, d, J = 10.5 Hz), 7.40-7.50 (3H, m), 7.55 (1H, d, J = 8.3 Hz), 7.59 (1H, s), 7.71 (1H, d, J = 10.5 Hz), 7.82-7.93 (2H, m), 8.43 (1H, s), 12.48-12.72 (1H, br).

Example 73
(E, E) -N- [4- (2,4-Dichlorobenzyloxymethyl) benzoyl] -4- (furan-2-yl) but-1,3-diene-1-sulfonamide
IRν (ATR) cm ^-1 ; 1691, 1606
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 4.61 (2H, s), 4.68 (2H, s), 6.60 (1H, dd, J = 3.4, 1.7 Hz), 6.73 (1H, d, J = 3.4 Hz), 6.84 (1H, dd, J = 15.4, 11.2 Hz), 6.99 (1H, d, J = 14.6 Hz), 7.11 (1H, d, J = 15.4 Hz), 7.39 (1H, dd, J = 14.6, 11.2 Hz), 7.46 (1H, dd, J = 8.3, 2.0 Hz), 7.45-7.52 (2H, m), 7.57 (1H, d, J = 8.3 Hz), 7.63 (1H, d , J = 2.0 Hz), 7.79 (1H, d, J = 1.7 Hz), 7.88-7.94 (2H, m), 12.10-12.35 (1H, br).

Example 74
N- [4- (4'-Isopropylbiphenyl-4-ylmethoxymethyl) benzoyl] octane-1-sulfonamide
IRν (ATR) cm ^-1 ; 1680, 1612
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.83 (3H, t, J = 6.8 Hz), 1.15-1.30 (14H, m), 1.33-1.45 (2H, m), 1.62- 1.77 (2H, m), 2.85-3.00 (1H, m), 3.51 (2H, t, J = 7.6 Hz), 4.60 (2H, s), 4.65 (2H, s), 7.29-7.37 (2H, m) , 7.40-7.47 (2H, m), 7.48-7.55 (2H, m), 7.53-7.61 (2H, m), 7.60-7.67 (2H, m), 7.89-7.97-8.15 (2H, m).

Example 75
N- [4- (Biphenyl-4-ylmethoxymethyl) benzoyl] dibenzothiophene-2-sulfonamide
IRν (ATR) cm ^-1 ; 1612
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 4.58 (2H, s), 4.62 (2H, s), 7.31-7.39 (1H, m), 7.40-7.72 (12H, m), 8.08 (1H, dd, J = 8.6, 1.7 Hz), 8.12-8.18 (1H, m), 8.08-8.18 (1H, m), 8.32 (1H, s), 8.49-8.58 (1H, m), 8.94 ( 1H, d, J = 1.5 Hz), 12.45-12.83 (1H, br).

Example 76
N- [4- (Biphenyl-4-ylmethoxymethyl) benzoyl] -6-chloronaphthalene-2-sulfonamide
IRν (ATR) cm ^-1 ; 1614
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 4.59 (2H, s), 4.62 (2H, s), 7.33-7.40 (1H, m), 7.41-7.52 (6H, m), 7.60-7.68 (4H, m), 7.72 (1H, dd, J = 8.8, 2.0 Hz), 7.82-7.90 (2H, m), 8.01 (1H, dd, J = 8.8, 1.7 Hz), 8.14 (1H, d, J = 8.8 Hz), 8.19-8.24 (1H, m), 8.31 (1H, d, J = 8.8 Hz), 8.74 (1H, s), 12.50-12.85 (1H, br).

Example 77
2,4-Dichloro-N- (6- {4-[(E) -5-methyl-1-hexenyl] phenoxy} benzofuran-2-carbonyl) benzenesulfonamide
IRν (ATR) cm ^-1 ; 1622
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.89 (6H, d, J = 6.6 Hz), 1.27-1.40, (2H, m), 1.51-1.66 (1H, m), 2.12 -2.23 (2H, m), 6.16-6.26 (1H, m), 6.38 (1H, d, J = 15.9 Hz), 6.92-7.02 (3H, m), 7.22-7.26 (1H, br), 7.34-7.49 (3H, m), 7.50-7.60 (1H, m), 7.62-7.68 (1H, br), 7.69 (1H, d, J = 8.6 Hz), 8.03 (1H, d, J = 8.6 Hz).

Example 78
(E) -2,4-Dichloro-N- {4- [4- (5-methyl-1-hexenyl) benzyloxymethyl] benzoyl} benzenesulfonamide sodium salt
IRν (ATR) cm ^-1 ; 1655
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.85 (6H, d, J = 6.6 Hz), 1.25-1.32 (2H, m), 1.48-1.58 (1H, m), 2.10- 2.19 (2H, m), 4.44 (2H, s), 4.82 (2H, s), 6.23 (1H, dt, J = 16.1, 6.8 Hz), 6.35 (1H, d, J = 16.1 Hz), 7.21-7.28 (4H, m), 7.30-7.35 (2H, m), 7.44 (1H, dd, J = 8.6, 2.2 Hz), 7.49 (1H, d, J = 2.2 Hz), 7.80-7.86 (2H, m), 7.96 (1H, d, J = 8.6 Hz).

Example 79
N- [4- (Biphenyl-4-ylmethoxymethyl) benzoyl] -2,6-dichlorobenzenesulfonamide
IRν (ATR) cm ^-1 ; 1668, 1610
¹ H-NMR (CDCl ₃ , 400 MHz) δ (ppm); 4.60-4.66 (4H, m), 7.32-7.63 (14H, m), 7.77-7.85 (2H, m), 9.02-9.33 (1H, br ).

Example 80
2,4-Dichloro-N- [4- (4'-fluorobiphenyl-4-ylmethoxymethyl) benzoyl] benzenesulfonamide sodium salt
IRν (ATR) cm ^-1 ; 1728, 1593
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 4.53-4.60 (4H, br), 7.23-7.35 (4H, m), 7.39-7.50 (3H, m), 7.50-7.54 (1H , m), 7.60-7.68 (2H, m), 7.67-7.75 (2H, m), 7.83-7.93 (2H, m), 7.99 (1H, d, J = 8.5 Hz).

Example 81
2,4-Dichloro-N- [4- (4'-chlorobiphenyl-4-ylmethoxymethyl) benzoyl] benzenesulfonamide
IRν (ATR) cm ^-1 ; 1728
¹ H-NMR (CDCl ₃ , 400 MHz) δ (ppm); 4.62 (2H, s), 4.63 (2H, s), 7.35-7.62 (12H, m), 7.75-7.83 (2H, m), 8.31 ( 1H, d, J = 8.6 Hz), 8.95-9.23 (1H, br).

Example 82
N- {4- [4 '-(trifluoromethyl) biphenyl-4-ylmethoxymethyl] benzoyl} octane-1-sulfonamide
IRν (ATR) cm ^-1 ; 1677, 1332, 1159
¹ H-NMR (CDCl ₃ , 400 MHz) δ (ppm); 0.83 (3H, t, J = 6.6 Hz), 1.16-1.28 (8H, m), 1.33-1.43 (2H, m), 1.64-1.74 ( 2H, m), 3.47-3.53 (2H, m), 4.64 (2H, s), 4.66 (2H, s), 7.49-7.53 (4H, m), 7.73-7.76 (2H, m), 7.80-7.82 ( 2H, m), 7.88-7.91 (2H, m), 7.92-7.95 (2H, m), 12.00-12.08 (1H, br).

Example 83
N- [4- (2,4-Dichlorobenzyloxymethyl) benzoyl] biphenyl-4-sulfonamide
IRν (ATR) cm ^-1 ; 1658, 1612
¹ H-NMR (CDCl ₃ , 400 MHz) δ (ppm); 4.60 (2H, s), 4.65 (2H, s), 7.20-7.87 (14H, m), 8.22 (2H, m), 8.95 (1H, m).

Example 84
N- [4- (4-Chlorobenzyloxymethyl) benzoyl] -2,4-dichlorobenzenesulfonamide
IRν (ATR) cm ^-1 ; 1689, 1608
¹ H-NMR (CDCl ₃ , 400 MHz) δ (ppm); 4.55 (2H, s), 4.60 (2H, s), 7.33-7.54 (6H, m), 7.66-7.80 (1H, m), 7.86- 7.98 (3H, m), 8.17 (1H, d, J = 8.6 Hz), 12.50-13.70 (1H, br).

Example 85
2,4-Dichloro-N- [6- (4-isopropylphenoxy) -1H-indole-2-carbonyl] benzenesulfonamide
IRν (ATR) cm ^-1 ; 1678, 1604
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 1.19 (6H, d, J = 6.8 Hz), 2.80-2.95 (1H, m), 6.80-6.88 (2H, m), 6.91- 6.98 (2H, m), 7.20-7.30 (2H, m), 7.60 (1H, s), 7.66 (1H, d, J = 8.8 Hz), 7.72 (1H, dd, J = 8.6, 2.0 Hz), 7.85 -7.90 (1H, m), 8.17 (1H, d, J = 8.6 Hz), 11.50-11.60 (1H, m), 12.70-13.30 (1H, br).

Example 86
N- [4- (Biphenyl-4-ylmethoxymethyl) benzoyl] -5-hydroxypentane-1-sulfonamide
IRν (ATR) cm ^-1 ; 1678, 1612
¹ H-NMR (CDCl ₃ , 400 MHz) δ (ppm); 1.48-1.75 (4H, m), 1.80-2.00 (2H, m), 3.55-3.68 (4H, m), 4.64 (1H, s), 4.64 (1H, s), 7.30-7.38 (1H, m), 7.39-7.47 (4H, m), 7.47-7.54 (2H, m), 7.56-7.65 (4H, m), 7.80-7.89 (1H, m ), 8.45-9.10 (1H, br).

Example 87
(E, E, E) -N- [4- (2,4-Dichlorobenzyloxymethyl) benzoyl] hepta-1,3,5-triene-1-sulfonamide sodium salt
IRν (ATR) cm ^-1 ; 1670
¹ H-NMR (DMSO-d6, 400 MHz) δ (ppm); 1.76 (3H, d, J = 6.6 Hz), 4.58 (2H, s), 4.62 (2H, s), 5.80-5.95 (1H, m ), 6.08-6.24 (2H, m), 6.48 (1H, dd, J = 14.9, 10.7 Hz), 6.71-6.90 (2H, m), 7.27-7.35 (2H, m), 7.42-7.49 (1H, m ), 7.56 (1H, d, J = 8.3 Hz), 7.58-7.63 (1H, m), 7.87-7.94 (2H, m).

Example 88
N- [4- (Biphenyl-4-ylmethoxymethyl) benzoyl] pentane-1-sulfonamide
IRν (ATR) cm ^-1 ; 1676
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.83 (3H, t, J = 7.1 Hz), 1.21-1.41 (4H, m), 1.62-167 (2H, m), 3.46- 3.54 (2H, m), 4.61 (2H, s), 4.64 (2H, s), 7.33-7.38 (1H, m), 7.43-7.53 (6H, m), 7.63-7.68 (4H, m), 7.90- 7.95 (2H, m), 11.50-12.50 (1H, br).

Example 89
N- [4 '-(biphenyl-4-ylmethoxymethyl) biphenyl-2-carbonyl] methanesulfonamide sodium salt
IRν (ATR) cm ^-1 ; 1601
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 2.63 (3H, s), 4.51 (2H, s), 4.54 (2H, s), 7.16-7.32 (7H, m), 7.36- 7.43 (6H, m), 7.57-7.62 (4H, m).

Example 90
N- [4- (Benzyloxymethyl) benzoyl] biphenyl-4-sulfonamide
IRν (ATR) cm ^-1 ; 1708, 1348, 1162
¹ H-NMR (CDCl ₃ , 400 MHz) δ (ppm); 4.54 (2H, s), 4.60 (2H, s), 7.26-7.38 (5H, m), 7.42-7.54 (5H, m), 7.73- 7.76 (2H, m), 7.86-7.88 (2H, m), 7.91-7.94 (2H, m), 8.04-8.08 (2H, m), 12.50-13.65 (1H, br).

Example 91
N- [4- (2,4-Dichlorobenzyloxymethyl) benzoyl] -2,4-dichlorobenzenesulfonamide
IRν (ATR) cm ^-1 ; 1698, 1569
¹ H-NMR (CDCl ₃ , 400 MHz) δ (ppm); 4.61 (2H, s), 4.68 (2H, s), 7.43-7.50 (3H, m), 7.54-7.58 (1H, m), 7.61- 7.64 (1H, m), 7.70-7.74 (1H, m), 7.88-7.92 (3H, m), 8.10-8.18 (1H, m).

Example 92
N- [4- (2-Chlorobenzyloxymethyl) benzoyl] -2,4-dichlorobenzenesulfonamide
IRν (ATR) cm ^-1 ; 1697, 1168
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 4.63 (2H, s), 4.68 (2H, s), 7.33-7.56 (6H, m), 7.71-7.74 (1H, m), 7.88-7.92 (3H, m), 8.14-8.19 (1H, m).

Example 93
N- [4- (4-Isopropylbenzyloxymethyl) benzoyl] octane-1-sulfonamide
IRν (ATR) cm ^-1 ; 1679, 1336, 1157
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.80-0.88 (3H, m), 1.16-1.28 (14H, m), 1.33-1.45 (2H, m), 1.63-1.75 (2H , m), 2.83-2.95 (1H, m), 3.46-3.54 (2H, m), 4.52 (2H, s), 4.60 (2H, s), 7.21-7.31 (4H, m), 7.43-7.52 (2H , m), 7.90-7.94 (2H, m), 12.00-12.08 (1H, br).

Example 94
N- [4- (4-Isopropylbenzyloxymethyl) benzoyl] naphthalene-2-sulfonamide
IRν (ATR) cm ^-1 ; 1693, 1330, 1168
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 1.19 (6H, d, J = 6.8 Hz), 2.81-2.93 (1H, m), 4.49 (2H, s), 4.57 (2H, s), 7.19-7.27 (4H, m), 7.41-7.49 (2H, m), 7.67-7.79 (2H, m), 7.83-7.85 (2H, m), 7.94-7.97 (1H, m), 8.05- 8.07 (1H, m), 8.14-8.16 (1H, m), 8.23-8.25 (1H, m), 8.68-8.67 (1H, m), 12.54-12.69 (1H, br).

Example 95
2,4-Dichloro-N- [4- (4-isopropylthiophen-2-ylmethoxymethyl) benzoyl] benzenesulfonamide
IRν (ATR) cm ^-1 ; 1693, 1353, 1174
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 1.24 (6H, d, J = 6.8 Hz), 1.25 (3H, s), 2.89-2.99 (1H, m), 4.64 (2H, s), 4.71 (2H, s), 7.06 (2H, s), 7.15 (2H, s), 7.44-7.48 (2H, m), 7.71-7.75 (1H, m), 7.85-7.91 (1H, m) , 7.92-7.96 (2H, m), 8.17-8.21 (1H, m).

Example 96
N- [4- (2,4-Dichlorobenzyloxymethyl) benzoyl] octane-1-sulfonamide
IRν (ATR) cm ^-1 ; 1677, 1338, 1159
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.81-0.84 (3H, m), 1.18-1.28 (14H, m), 1.34-1.43 (2H, m), 1.65-1.74 (2H , m), 3.47-3.53 (2H, m), 4.62 (2H, s), 4.69 (2H, s), 7.46 (1H, dd, J = 8.3, 2.2 Hz), 7.48-7.51 (2H, m), 7.57 (1H, d, J = 8.3 Hz), 7.63 (1H, d, J = 2.2 Hz), 7.90-7.93 (2H, m), 12.01-12.08 (1H, br).

Example 97
N- {4- [2- (2,4-dichlorophenyl) ethoxy] benzoyl} octane-1-sulfonamide
IRν (ATR) cm ^-1 ; 1675, 1330, 1139
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.80-0.84 (3H, m), 1.15-1.28 (8H, m), 1.34-1.39 (2H, m), 1.62-1.72 (2H , m), 3.18 (2H, t, J = 6.7 Hz), 3.45-3.51 (2H, m), 4.29 (2H, t, J = 6.7 Hz), 7.00-7.06 (2H, m), 7.41 (1H, dd, J = 8.3, 2.2 Hz), 7.50 (1H, d, J = 8.3 Hz), 7.62 (1H, d, J = 2.2 Hz), 7.88-7.92 (2H, m), 11.81-11.87 (1H, br ).

Example 98
N- [4- (2,4-Dichlorobenzyloxymethyl) benzoyl] cyclohexanesulfonamide
IRν (ATR) cm ^-1 ; 1698, 1336, 1155
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 1.14-1.65 (6H, m), 1.80-1.84 (2H, m), 2.01-2.06 (2H, m), 3.53-3.61 (1H , m), 4.62 (2H, s), 4.69 (2H, s), 7.46 (1H, dd, J = 8.3, 2.0 Hz), 7.48-7.52 (2H, m), 7.57 (1H, d, J = 8.3 Hz), 7.63 (1H, d, J = 2.0 Hz), 7.91-7.94 (2H, m), 11.93-12.00 (1H, br).

Example 99
N- [4- (2,4-Dichlorobenzyloxymethyl) benzoyl] cyclopentanesulfonamide
IRν (ATR) cm ^-1 ; 1693, 1334, 1153
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 1.56-1.75 (4H, m), 1.92-2.02 (4H, m), 4.11-4.20 (1H, m), 4.62 (2H, s ), 4.69 (2H, s), 7.46 (1H, dd, J = 8.3, 2.1 Hz), 7.49-7.52 (2H, m), 7.57 (1H, d, J = 8.3 Hz), 7.63 (1H, d, J = 2.1 Hz), 7.90-7.93 (2H, m), 11.98-12.03 (1H, br).

Example 100
N- [4- (2,4-Dichlorobenzyloxymethyl) benzoyl] -3,5-dimethylisoxazole-4-sulfonamide
IRν (ATR) cm ^-1 ; 1654, 1349, 1124
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 2.40 (3H, s), 2.70 (3H, s), 4.61 (2H, s), 4.68 (2H, s), 7.46 (1H, dd, J = 8.3, 2.2 Hz), 7.48-7.50 (2H, m), 7.56 (1H, d, J = 8.3 Hz), 7.63 (1H, d, J = 2.2 Hz), 7.87-7.91 (2H, m ).

Example 101
N- [4- (2,4-Dichlorobenzyloxymethyl) benzoyl] dodecane-1-sulfonamide
IRν (ATR) cm ^-1 ; 1677, 1338, 1157
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.81-0.88 (3H, m), 1.18-1.28 (16H, m), 1.33-1.43 (2H, m), 1.64-1.74 (2H , m), 3.47-3.54 (2H, m), 4.62 (2H, s), 4.69 (2H, s), 7.44-7.52 (3H, m), 7.55-7.59 (1H, m), 7.61-7.63 (1H , m), 7.90-7.94 (2H, m), 12.01-12.08 (1H, br).

Example 102
N- [4- (Biphenyl-4-ylmethoxymethyl) benzoyl] biphenylsulfonamide
IRν (ATR) cm ^-1 : 1697, 1340, 1166
¹ H-NMR (CDCl ₃ , 400 MHz) δ (ppm); 4.60 (2H, s), 4.63 (2H, s), 7.32-7.38 (1H, m), 7.41-7.54 (9H, m), 7.63- 7.67 (4H, m), 7.73-7.76 (2H, m), 7.87-7.90 (2H, m), 7.90-7.95 (2H, m), 8.00-8.09 (2H, m), 12.53-12.67 (1H, br ).

Example 103
N- [4- (2,4-Dichlorobenzyloxymethyl) benzoyl] indan-2-sulfonamide
IRν (ATR) cm ^-1 ; 1693, 1328, 1072
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 3.40-3.42 (4H, m), 4.61-4.71 (5H, m), 7.15-7.18 (2H, m), 7.23-7.26 (2H , m), 7.47 (1H, dd, J = 8.3, 2.0 Hz), 7.50-7.53 (2H, m), 7.58 (1H, d, J = 8.3 Hz), 7.64 (1H, d, J = 2.0 Hz) , 7.91-7.94 (2H, m), 12.11-12.20 (1H, br).

Example 104
2- [4- (Biphenyl-4-ylmethoxymethyl) benzoylsulfamoyl] benzoic acid
IRν (ATR) cm ^-1 ; 1724, 1687
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 4.60 (2H, s), 4.63 (2H, s), 7.33-7.40 (1H, m), 7.42-7.52 (6H, m), 7.63-7.80 (7H, m), 7.88-7.95 (2H, m), 8.10-8.17 (1H, m), 11.50-14.50 (2H, br).

Example 105
N- [4- (Biphenyl-4-ylmethoxymethyl) benzoyl] octane-1-sulfonamide
IRν (ATR) cm ^-1 ; 1675
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.80-0.86 (3H, m), 1.15-1.31 (8H, m), 1.34-1.45 (2H, m), 1.65-1.75 (2H , m), 3.46-3.55 (2H, m), 4.62 (2H, s), 4.65 (2H, s), 7.33-7.39 (1H, m), 7.43-7.55 (6H, m), 7.65-7.70 (4H , m), 7.91-7.97 (2H, m), 12.05 (1H, s).

Example 106
N- [4- (Naphthalen-1-ylmethoxymethyl) benzoyl] naphthalene-2-sulfonamide
IRν (ATR) cm ^-1 ; 1697
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 4.66 (2H, s), 4.98 (2H, s), 7.40-7.60 (6H, m), 7.64-7.77 (2H, m), 7.80-7.86 (2H, m), 7.88 (1H, d, J = 8.3 Hz), 7.91-7.98 (2H, m), 8.02-8.11 (2H, m), 8.13 (1H, d, J = 8.8 Hz) , 8.20-8.27 (1H, m), 8.64-8.71 (1H, m), 12.5-12.7 (1H, br).

Example 107
N- [3- (biphenyl-4-ylmethoxymethyl) benzoyl] octane-1-sulfonamide
IRν (ATR) cm ^-1 ; 1654
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.79-0.87 (3H, m), 1.16-1.31 (8H, m), 1.34-1.45 (2H, m), 1.65-1.75 (2H , m), 3.46-3.55 (2H, m), 4.62 (2H, s), 4.63 (2H, s), 7.33-7.39 (1H, m), 7.43-7.55 (5H, m), 7.62-7.70 (5H , m), 7.83-7.88 (1H, m), 7.94 (1H, s), 12.10 (1H, s).

Example 108
N- [4- (Biphenyl-4-ylmethoxymethyl) benzoyl] -2-cyanobenzenesulfonamide
IRν (ATR) cm ^-1 ; 1698
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 4.64 (2H, s), 4.70 (2H, s), 7.33-7.39 (1H, m), 7.44-7.52 (4H, m), 7.57-7.64 (2H, m), 7.65-7.72 (4H, m), 7.86-7.96 (2H, m), 7.98-8.04 (2H, m), 8.12-8.18 (1H, m), 8.48-8.56 (1H , m), 11.64-11.75 (1H, br).

Example 109
N- [4- (Benzhydryloxymethyl) benzoyl] octane-1-sulfonamide
IRν (ATR) cm ^-1 ; 1668
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.79-0.86 (3H, m), 1.15-1.30 (8H, m), 1.32-1.44 (2H, m), 1.65-1.75 (2H , m), 3.46-3.55 (2H, m), 4.56 (2H, s), 5.58 (1H, s), 7.22-7.28 (2H, m), 7.31-7.38 (4H, m), 7.38-7.46 (4H , m), 7.46-7.53 (2H, m), 7.87-7.95 (2H, m), 12.04 (1H, s).

Example 110
2,4-Dichloro-N- [4 '-(4-isopropylphenoxy) biphenyl-4-carbonyl] benzenesulfonamide
IRν (ATR) cm ^-1 ; 1691, 1349, 1166
¹ H-NMR (CDCl ₃ , 400 MHz) δ (ppm); 1.21 (6H, d, J = 6.8 Hz), 2.91 (1H, heptet, J = 6.8 Hz), 6.99-7.02 (2H, m), 7.04 -7.07 (2H, m), 7.27-7.30 (2H, m), 7.71-7.78 (5H, m), 7.97-8.00 (2H, m), 8.16-8.18 (1H, m).

Example 111
N- [4 '-(4-Isopropylphenoxy) biphenyl-4-carbonyl] indan-2-sulfonamide
IRν (ATR) cm ^-1 ; 1691, 1326, 1143
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 1.22 (6H, d, J = 6.8 Hz), 2.91 (1H, heptet, J = 6.8 Hz), 3.42 (4H, d, J = 7.6 Hz), 4.68 (1H, quintet, J = 7.6 Hz), 7.00-7.03 (2H, m), 7.06-7.09 (2H, m), 7.16-7.27 (4H, m), 7.28-7.31 (2H, m ), 7.76-7.78 (2H, m), 7.79-7.82 (2H, m), 7.99-8.02 (2H, m), 12.15-12.23 (1H, br).

Example 112
N- [4 '-(4-Isopropylphenoxy) benzoyl] -9H-fluorene-9-sulfonamide
IRν (ATR) cm ^-1 ; 1738, 1689, 1591, 1500
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 1.23 (6H, d, J = 6.8 Hz), 2.94 (1H, heptet, J = 6.8 Hz), 6.24 (1H, s), 7.04 -7.13 (4H, m), 7.33-7.44 (4H, m), 7.50-7.57 (2H, m), 7.60-7.66 (2H, m), 7.95-8.01 (2H, m), 8.06-8.12 (2H, m), 12.00-13.00 (1H, br).

Example 113
N- {5- [4- (4-Isopropylphenoxy) phenyl] pyridine-2-carbonyl} octane-1-sulfonamide
IRν (ATR) cm ^-1 ; 1725, 1702
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.79-0.86 (3H, m), 1.18-1.31 (14H, m), 1.34-1.45 (2H, m), 1.66-1.77 (2H , m), 2.85-2.96 (2H, m), 3.47-3.55 (2H, m), 6.99-7.06 (2H, m), 7.08-7.15 (2H, m), 7.26-7.33 (2H, m), 7.82 -7.87 (2H, m), 8.12 (1H, d, J = 8.1 Hz), 8.28-8.35 (1H, m), 8.88-9.02 (1H, m), 11.60-11.85 (1H, br).

Example 114
N- [5- (4-Isopropylphenoxy) indan-2-carbonyl] naphthalene-2-sulfonamide
IRν (ATR) cm ^-1 ; 1724
¹ H-NMR (CDCl ₃ , 400 MHz) δ (ppm); 1.23 (6H, d, J = 6.8 Hz), 2.88 (1H, heptet, J = 6.8 Hz), 3.03-3.17 (4H, m), 3.21 -3.31 (1H, m), 6.74-6.80 (2H, m), 6.85-6.90 (2H, m), 7.06 (1H, d, J = 8.1Hz), 7.12-7.18 (2H, m), 7.60-7.71 (2H, m), 7.92 (1H, d, J = 8.1Hz), 7.97-8.04 (2H, m), 8.40 (1H, s), 8.68 (1H, s).

Example 115
2,4-Dichloro-N- [7- (4-isopropylphenoxy) quinoline-3-carbonyl] benzenesulfonamide
IRν (ATR) cm ^-1 ; 1645, 1606
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 1.24 (6H, d, J = 6.8 Hz), 2.88-3.02 (1H, m), 7.08-7.21 (2H, m), 7.25 ( 1H, s), 7.33-7.43 (2H, m), 7.50-7.61 (1H, m), 7.63-7.72 (1H, m), 7.81 (1H, s), 8.16 (1H, d, J = 8.6 Hz) , 8.24 (1H, d, J = 8.8 Hz), 9.08 (1H, s), 9.21 (1H, s).

Example 116
N- [5- (Benzyloxy) naphthalene-1-carbonyl] octane-1-sulfonamide
IRν (ATR) cm ^-1 ; 1677
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.81-0.88 (3H, m), 1.20-1.35 (8H, m), 1.40-1.52 (2H, m), 1.71-1.81 (2H , m), 3.56-3.65 (2H, m), 5.34 (2H, s), 7.18 (1H, d, J = 7.8 Hz), 7.31-7.39 (2H, m), 7.40-7.47 (2H, m), 7.51-7.62 (4H, m), 7.73 (1H, d, J = 8.5 Hz), 7.78 (1H, d, J = 6.4 Hz), 8.42 (1H, d, J = 8.5 Hz), 12.28 (1H, s ).

Example 117
N- [5- (biphenyl-4-ylmethoxy) naphthalene-1-carbonyl] octane-1-sulfonamide
IRν (ATR) cm ^-1 ; 1677
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.81-0.88 (3H, m), 1.20-1.35 (8H, m), 1.38-1.54 (2H, m), 1.70-1.81 (2H , m), 3.54-3.65 (2H, m), 5.40 (2H, s), 7.21 (1H, d, J = 7.6 Hz), 7.35-7.41 (1H, m), 7.45-7.82 (12H, m), 8.45 (1H, d, J = 8.6 Hz), 12.29 (1H, s).

Example 118
N- [4- (4-Isopropylbenzyloxymethyl) benzoyl] quinoline-6-sulfonamide
IRν (ATR) cm ^-1 ; 1687
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 1.17 (6H, d, J = 6.8 Hz), 2.78-2.98 (1H, m), 4.47 (2H, s), 4.56 (2H, s), 7.16-7.30 (4H, m), 7.38-7.48 (2H, m), 7.70 (1H, dd, J = 8.0, 4.2 Hz), 7.80-7.89 (2H, m), 8.15-8.27 (2H, m), 8.71 (1H, d, J = 8.0 Hz), 8.77 (1H, s), 9.04-9.13 (1H, m).

Example 119
N- [4- (4-Isopropylbenzyl) benzoyl] octane-1-sulfonamide
IRν (ATR) cm ^-1 ; 1699, 1647, 1606
¹ H-NMR (CDCl ₃ , 400 MHz) δ (ppm); 0.86 (3H, t, J = 6.8 Hz), 1.21-1.54 (8H, m), 1.23 (6H, d, J = 6.8 Hz), 1.37 -1.48 (2H, m), 1.79-1.90 (2H, m), 2.88 (1H, heptet, J = 6.8 Hz), 3.52-3.61 (2H, m), 4.01 (2H, s), 7.04-7.11 (2H , m), 7.13-7.19 (2H, m), 7.29-7.35 (2H, m), 7.73-7.78 (2H, m), 8.47 (1H, s).

Example 120
N- {4- [Benzyloxy (phenyl) methyl] benzoyl} naphthalene-2-sulfonamide
IRν (ATR) cm ^-1 ; 1693
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 4.44 (2H, s), 5.61 (1H, s), 7.22-7.41 (10H, m), 7.46-7.55 (2H, m), 7.64-7.76 (2H, m), 7.79-7.85 (2H, m), 7.92 (1H, dd, J = 8.8, 2.0 Hz), 8.03 (1H, d, J = 7.8 Hz), 8.12 (1H, d, J = 8.8 Hz), 8.22 (1H, d, J = 8.0 Hz), 8.63-8.69 (1H, m), 12.4-12.7 (1H, br).

Example 121
N- [4- (Biphenyl-4-ylmethoxymethyl) benzoyl] azocan-1-sulfonamide
IRν (ATR) cm ^-1 ; 1687
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 1.51-1.71 (10H, m), 3.30-3.42 (4H, m), 4.61 (2H, s), 4.64 (2H, s), 7.33-7.39 (1H, m), 7.42-7.52 (6H, m), 7.63-7.69 (4H, m), 7.88-7.95 (2H, m), 11.79 (1H, s).

Example 122
N- [4- (Biphenyl-4-ylmethylsulfanylmethyl) benzoyl] octane-1-sulfonamide
IRν (ATR) cm ^-1 ; 1678, 1441, 1336
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.83 (3H, t, J = 6.6 Hz), 1.15-1.30 (8H, m), 1.34-1.44 (2H, m), 1.65- 1.75 (2H, m), 3.47-3.54 (2H, m), 3.71 (2H, s), 3.77 (2H, s), 7.32-7.39 (3H, m), 7.42-7.48 (4H, m), 7.59- 7.68 (4H, m), 7.87-7.92 (2H, m), 12.01 (1H, s).

Example 123
N- [4- (biphenyl-4-ylmethylsulfinylmethyl) benzoyl] octane-1-sulfonamide
IRν (ATR) cm ^-1 ; 1658, 1456, 1340
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.83 (3H, t, J = 6.6 Hz), 1.15-1.30 (8H, m), 1.33-1.43 (2H, m), 1.64- 1.74 (2H, m), 3.46-3.57 (2H, m), 3.95 (1H, d, J = 12.7 Hz), 4.02 (1H, d, J = 12.7 Hz), 4.27 (1H, d, J = 12.7 Hz) ), 4.33 (1H, d, J = 12.7 Hz), 7.34-7.44 (3H, m), 7.44-7.51 (4H, m), 7.64-7.71 (4H, m), 7.91-7.96 (2H, m), 12.07 (1H, s).

Example 124
N- [4- (Biphenyl-4-ylmethylsulfonylmethyl) benzoyl] octane-1-sulfonamide
IRν (ATR) cm ^-1 ; 1660, 1458, 1342
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.83 (3H, t, J = 6.6 Hz), 1.15-1.30 (8H, m), 1.34-1.43 (2H, m), 1.65- 1.74 (2H, m), 3.46-3.56 (2H, m), 4.56 (2H, s), 4.63 (2H, s), 7.35-7.41 (1H, m), 7.44-7.51 (4H, m), 7.51- 7.56 (2H, m), 7.66-7.73 (4H, m), 7.93-7.98 (2H, m), 12.10 (1H, s).

Example 125
N- [4- (4-Isopropylbenzyloxymethyl) -3-phenoxybenzoyl] octane-1-sulfonamide
IRν (ATR) cm ^-1 ; 1687, 1660, 1457
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.82 (3H, t, J = 6.6 Hz), 1.16-1.27 (8H, m), 1.18 (6H, d, J = 6.8 Hz) , 1.31-1.40 (2H, m), 1.60-1.70 (2H, m), 2.87 (1H, heptet, J = 6.8 Hz), 3.42-3.51 (2H, m), 4.54 (2H, s), 4.62 (2H , s), 6.97-7.03 (2H, m), 7.15-7.27 (5H, m), 7.37-7.45 (3H, m), 7.64-7.69 (1H, m), 7.75-7.80 (1H, m), 12.08 (1H, s).

Example 126
N- [4- (2,4-Dichlorobenzyloxymethyl) benzoyl] -2,4-dichlorobenzylsulfonamide
IRν (ATR) cm ^-1 ; 1697, 1431, 1342
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 4.63 (2H, s), 4.69 (2H, s), 5.02 (2H, s), 7.47 (1H, dd, J = 8.3, 2.2 Hz), 7.48-7.54 (4H, m), 7.58 (1H, d, J = 8.3 Hz), 7.64 (1H, d, J = 2.2 Hz), 7.69 (1H, d, J = 2.0 Hz), 7.88- 7.93 (2H, m), 12.00-12.40 (1H, br).

Example 127
2,4-Dichloro-N- [4- (4-isopropylbenzyloxymethyl) -2-methoxybenzoyl] benzenesulfonamide sodium salt
IRν (ATR) cm ^-1 ; 1612, 1585, 1554, 1456.
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 1.19 (6H, d, J = 6.8 Hz), 2.87 (1H, quintet, J = 6.8 Hz), 3.64 (3H, s), 4.46 (2H, s), 4.48 (2H, s), 6.82 (1H, d, J = 7.6 Hz), 6.86 (1H, s), 7.19-7.29 (4H, m), 7.38 (1H, d, J = 7.6 Hz), 7.46 (1H, dd, J = 8.4, 2.2 Hz), 7.55 (1H, d, J = 2.2 Hz), 7.99 (1H, d, J = 8.4 Hz).

Example 128
2,4-Dichloro-N- {4- [4- (pyrrolidin-1-yl) benzyloxymethyl] benzoyl} benzenesulfonamide sodium salt
IRν (ATR) cm ^-1 ; 1570, 1523.
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 1.90-1.97 (4H, m), 3.19-3.24 (4H, m), 4.37 (2H, s), 4.44 (2H, s), 6.50 (2H, d, J = 8.5 Hz), 7.14 (2H, d, J = 8.5 Hz), 7.25 (2H, d, J = 8.3 Hz), 7.46 (1H, dd, J = 8.3, 2.2 Hz), 7.52 (1H, d, J = 2.2 Hz), 7.85 (2H, d, J = 8.3 Hz), 7.99 (2H, d, J = 8.5 Hz).

Example 129
(E) -2,4-Dichloro-N- {4- [4- (4-methylpent-1-enyl) benzyloxymethyl] benzoyl} benzenesulfonamide sodium salt
IRν (ATR) cm ^-1 ; 1593, 1554, 1322.
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.91 (6H, d, J = 6.6 Hz), 1.62-1.79 (1H, m), 2.04-2.11 (2H, m), 4.49 ( 2H, s), 4.52 (2H, s), 6.27 (1H, dt, J = 15.8, 6.8 Hz), 6.38 (1H, d, J = 15.8 Hz), 7.25-7.31 (4H, m), 7.35-7.40 (2H, m), 7.46 (1H, dd, J = 8.5, 2.2 Hz), 7.51 (1H, d, J = 2.2 Hz), 7.83-7.88 (2H, m), 7.99 (2H, d, J = 8.5 Hz).

Example 130
(E) -2,4-Dichloro-N- {2- [4- (4-methylpent-1-enyl) benzyloxy] indan-5-carbonyl} benzenesulfonamide sodium salt
IRν (ATR) cm ^-1 ; 1595, 1570, 1556, 1456.
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.91 (6H, d, J = 6.6 Hz), 1.60-1.75 (1H, m), 2.02-2.09 (2H, m), 2.85- 2.98 (2H, m), 3.06-3.17 (2H, m), 4.34-4.42 (1H, m), 4.49 (2H, s), 6.25 (1H, dt, J = 15.9, 6.8 Hz), 6.36 (1H, d, J = 15.9 Hz), 7.13 (1H, d, J = 7.7 Hz), 7.21-7.37 (4H, m), 7.45 (1H, dd, J = 8.3, 2.2 Hz), 7.50 (1H, d, J = 2.2 Hz), 7.67 (1H, d, J = 7.7 Hz), 7.42 (1H, s), 7.97 (1H, d, J = 8.3 Hz).

Example 131
(E) -2,4-Dichloro-N- [4- (4-styrylbenzyloxymethyl) benzoyl] benzenesulfonamide
IRν (ATR) cm ^-1 ; 1594, 1572, 1554.
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 4.52 (2H, s), 4.55 (2H, s), 7.22-7.41 (8H, m), 6.36 (1H, d, J = 15.9 Hz), 7.13 (1H, d, J = 7.7 Hz), 7.46 (1H, dd, J = 8.3, 2.2 Hz), 7.49 (1H, d, J = 2.2 Hz), 7.51 (1H, d, J = 2.2 Hz), 7.56-7.63 (3H, m), 7.88 (2H, d, J = 8.3 Hz), 7.89 (1H, d, J = 8.3 Hz), 7.99 (1H, d, J = 8.3 Hz).

Example 132
(E) -N- {5- [2- (4-Isopropylphenyl) vinyl] pyridine-2-carbonyl} naphthalene-2-sulfonamide
IRν (ATR) cm ^-1 ; 1522, 1375
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 1.20 (6H, d, J = 6.8 Hz), 2.88 (1H, heptet, J = 6.8 Hz), 7.24-7.29 (2H, m) , 7.34 (1H, d, J = 16.6 Hz), 7.52 (1H, d, J = 16.6 Hz), 7.55-7.65 (4H, m), 7.94-8.10 (5H, m), 8.19 (1H, dd, J = 8.3, 2.0 Hz), 8.53-8.57 (1H, br), 8.93-9.09 (1H, br).

Example 133
(E) -N- [4- (4-Isopropylbenzyloxymethyl) benzoyl] -2- (naphthalen-2-yl) ethenesulfonamide
IR ν (ATR) cm ^-1 ; 1687
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 1.18 (6H, d, J = 6.8 Hz), 2.86 (1H, heptet, J = 6.8 Hz), 4.47 (2H, s), 4.52 (2H, s), 7.19-7.23 (2H, m), 7.23-7.36 (5H, m), 7.48-7.54 (3H, m), 7.69-7.74 (1H, m), 7.87-7.95 (5H, m) , 8.02-8.05 (1H, br).

Example 134
N- [4- (4-Isopropylbenzyloxymethyl) benzoyl] -2- (naphthalen-2-yl) ethane-1-sulfonamide
IR ν (ATR) cm ^-1 ; 1687
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 1.19 (6H, d, J = 6.8 Hz), 2.87 (1H, heptet, J = 6.8 Hz), 3.19-3.25 (2H, m) , 3.90-3.96 (2H, m), 4.50 (2H, s), 4.57 (2H, s), 7.20-7.25 (2H, m), 7.25-7.30 (2H, m), 7.37-7.48 (5H, m) , 7.76-7.83 (6H, m), 8.02-8.05 (1H, br), 12.02-12.21 (1H, br).

Example 135
N- [4- (9H-carbazol-9-ylmethyl) benzoyl] octane-1-sulfonamide
IR ν (ATR) cm ^-1 ; 3261, 1689
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.77-0.82 (3H, m), 1.14-1.24 (8H, m), 1.29-1.38 (2H, m), 1.59-1.68 (2H , m), 3.42-3.48 (2H, m), 5.75 (2H, s), 7.19-7.25 (4H, m), 7.39-7.44 (2H, m), 7.57-7.61 (2H, m), 7.79-7.83 (2H, m), 8.16-8.20 (2H, m), 11.88-11.97 (1H, br).

Example 136
(E) -N- (2- {2- [4- (4-Isopropylbenzyloxymethyl) phenyl] vinyl} benzoyl) methanesulfonamide
IR ν (ATR) cm ^-1 ; 1689
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 1.19 (6H, d, J = 6.8 Hz), 2.87 (1H, heptet, J = 6.8 Hz), 3.06 (3H, s), 4.48 (2H, s), 4.52 (2H, s), 7.20-7.24 (2H, m), 7.25-7.29 (3H, m), 7.34-7.42 (4H, m), 7.51-7.57 (4H, m), 7.87 (1H, d, J = 7.8 Hz), 12.23-12.36 (1H, br).

Example 137
N- [5- (4-Isopropylphenoxy) quinoline-8-carbonyl] naphthalene-2-sulfonamide
IRν (ATR) cm ^-1 ; 1693
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 1.21 (6H, d, J = 6.8 Hz), 2.86-2.98 (1H, m), 6.86 (1H, d, J = 8.6 Hz) , 7.13-7.19 (2H, m), 7.33-7.39 (2H, m), 7.65-7.75 (2H, m), 7.81-7.89 (1H, m), 8.01-8.08 (2H, m), 8.13 (1H, d, J = 8.8 Hz), 8.23 (1H, d, J = 7.8 Hz), 8.40 (1H, d, J = 8.6 Hz), 8.78 (1H, s), 8.87-8.96 (1H, m), 9.20- 9.28 (1H, m), 12.65-12.35 (1H, br).

Example 138
N- [1- (4-Isopropylbenzyl) -2,3-dihydro-1H-indole-5-carbonyl] naphthalene-2-sulfonamide
IR ν (ATR) cm ^-1 ; 1673, 1604
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 1.16 (6H, d, J = 7.1 Hz), 2.80-3.00 (3H, m), 3.44 (2H, t, J = 8.1 Hz) , 6.57 (1H, d, J = 8.3 Hz), 7.15-7.23 (4H, m), 7.50 (1H, s), 7.61 (1H, dd, J = 8.6, 2.0 Hz), 7.65-7.75 (2H, m ), 7.92 (1H, dd, J = 8.8, 2.0 Hz), 8.04 (1H, d, J = 7.8 Hz), 8.12 (1H, d, J = 8.8 Hz), 8.21 (1H, d, J = 7.8 Hz) ), 8.63 (1H, s), 11.98 (1H, s).

Example 139
N- [4- (biphenyl-4-ylmethoxymethyl) benzoyl] -3-butoxypropane-1-sulfonamide
IRν (ATR) cm ^-1 ; 1691
¹ H-NMR (CDCl ₃ , 400 MHz) δ (ppm); 0.90 (3H, t, J = 7.3 Hz), 1.26-1.38 (2H, m), 1.47-1.56 (2H, m), 2.07-2.18 ( 2H, m), 3.39 (2H, t, J = 6.6 Hz), 3.53 (2H, t, J = 5.9 Hz), 3.67-3.75 (2H, m), 4.64 (2H, s), 4.66 (2H, s ), 7.31-7.39 (1H, m), 7.40-7.47 (4H, m), 7.49-7.56 (2H, m), 7.56-7.63 (4H, m), 7.78-7.86 (2H, m), 8.37-8.48 (1H, br).

Example 140
4-Cyano-N- [4- (4-isopropylbenzyloxymethyl) benzoyl] benzenesulfonamide
IRν (ATR) cm ^-1 ; 2235, 1718
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 1.19 (6H, d, J = 6.8 Hz), 2.83-2.93 (1H, m), 4.50 (2H, s), 4.58 (2H, s), 7.20-7.29 (4H, m), 7.43-7.49 (2H, m), 7.82-7.89 (2H, m), 8.09-8.17 (4H, m).

Example 141
N- [4- (4-Isopropylbenzyloxymethyl) benzoyl] naphthalene-1-sulfonamide
IRν (ATR) cm ^-1 ; 1693
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 1.18 (6H, d, J = 6.8 Hz), 2.77-2.95 (1H, m), 4.48 (2H, s), 4.55 (2H, s), 7.16-7.26 (4H, m), 7.39-7.45 (2H, m), 7.60-7.70 (1H, m), 7.72-7.79 (2H, m), 7.80-7.88 (2H, m), 8.08- 8.15 (1H, m), 8.28-8.35 (1H, m), 8.40-8.47 (1H, m), 8.70-8.77 (1H, m), 12.65-12.35 (1H, br).

Example 142
N- [4- (4-Isopropylphenylsulfanyl) benzoyl] naphthalene-2-sulfonamide
IRν (ATR) cm ^-1 ; 1589
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 1.19 (6H, d, J = 7.1 Hz), 2.84-2.94 (1H, m), 7.12-7.19 (2H, m), 7.23- 7.32 (4H, m), 7.52-7.60 (2H, m), 7.80-7.94 (5H, m), 7.98-8.06 (1H, m), 8.35 (1H, s).

Example 143
N- [4- (4-Isopropylbenzyloxymethyl) benzoyl] biphenyl-2-sulfonamide
IR ν (ATR) cm ^-1 ; 1695
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 1.19 (6H, d, J = 6.8 Hz), 2.83-2.95 (1H, m), 4.51 (2H, s), 4.57 (2H, s), 7.21-7.43 (12H, m), 7.55-7.75 (4H, m), 8.17 (1H, d, J = 8.0 Hz), 11.90-12.15 (1H, br).

Example 144
N- [4- (4-Isopropylbenzyloxymethyl) benzoyl] -2-hydroxybenzenesulfonamide
IR ν (ATR) cm ^-1 ; 1675
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 1.19 (6H, d, J = 6.8 Hz), 2.82-2.95 (1H, m), 4.50 (2H, s), 4.58 (2H, s), 6.93-7.01 (2H, m), 7.20-7.30 (4H, m), 7.40-7.52 (3H, m), 7.81 (1H, dd, J = 8.0, 1.7 Hz), 7.86-7.93 (2H, m), 10.73-11.50 (1H, br), 12.00-12.60 (1H, br).

Example 145
N- [4- (4-Isopropylbenzyloxymethyl) benzoyl] -2-cyclohexylethane-1-sulfonamide
IR ν (ATR) cm ^-1 ; 1689
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.79-0.91 (2H, m), 1.03-1.25 (10H, m), 1.29-1.41 (1H, m), 1.53-1.69 (6H , m), 2.87 (1H, heptet, J = 6.8 Hz), 3.48-3.54 (2H, m), 4.51 (2H, s), 4.59 (2H, s), 7.20-7.24 (2H, m), 7.25- 7.29 (2H, m), 7.45-7.49 (2H, m), 7.88-7.93 (2H, m), 11.98-12.07 (1H, br).

Example 146
N- [4- (4-Isopropylphenylethynyl) benzoyl] naphthalene-2-sulfonamide
IRν (ATR) cm ^-1 ; 1702, 1600
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 1.20 (6H, d, J = 7.1 Hz), 2.86-2.97 (1H, m), 7.28-7.35 (2H, m), 7.47- 7.53 (2H, m), 7.60-7.66 (2H, m), 7.67-7.78 (2H, m), 7.86-7.92 (2H, m), 7.97 (1H, dd, J = 8.8, 2.0 Hz), 8.06 ( 1H, dd, J = 8.0 Hz), 8.16 (1H, d, J = 8.8 Hz), 8.25 (1H, d, J = 8.0 Hz), 8.70 (1H, s), 12.50-13.00 (1H, br).

Example 147
4- (4-Isopropylbenzyloxymethyl) -N- (heptylaminosulfonyl) benzamide
IRν (ATR) cm ^-1 ; 1662
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.78-0.86 (3H, m), 1.15-1.27 (16H, m), 1.37-1.50 (2H, m), 2.83-2.96 (1H , m), 4.51 (2H, s), 4.59 (2H, s), 70-7.30 (4H, m), 7.43-7.50 (2H, m), 7.75 (1H, t, J = 5.6 Hz), 7.86- 7.95 (2H, m), 11.72 (1H, br).

Example 148
N- [4- (4-Isopropylbenzyloxymethyl) benzoyl] -2-nitrobenzenesulfonamide
IRν (ATR) cm ^-1 ; 1697
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 1.19 (6H, d, J = 6.8 Hz), 2.88 (1H, heptet, J = 6.8 Hz), 4.51 (2H, s), 4.59 (2H, s), 7.19-7.23 (2H, m), 7.24-7.28 (2H, m), 7.44-7.49 (2H, m), 7.88-7.96 (4H, m), 7.98-8.03 (1H, m) , 8.23-8.40 (1H, m).

Example 149
2-Amino-N- [4- (4-isopropylbenzyloxymethyl) benzoyl] benzenesulfonamide
IRν (ATR) cm ^-1 ; 1697
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 1.19 (6H, d, J = 6.8 Hz), 2.88 (1H, heptet, J = 6.8 Hz), 4.50 (2H, s), 4.58 (2H, s), 6.61-6.68 (1H, m), 7.88-7.96 (1H, m), 7.20-7.33 (5H, m), 7.43-7.48 (2H, m), 7.64-7.58 (1H, m) , 7.82-7.88 (2H, m).

Example 150
2-Chloro-4-hydroxy-N- [4- (4-isopropylbenzyloxymethyl) benzoyl] benzenesulfonamide
IRν (ATR) cm ^-1 ; 1675, 1594
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 1.19 (6H, d, J = 7.1 Hz), 2.88 (1H, heptet, J = 7.1 Hz), 4.49 (2H, s), 4.56 (2H, s), 6.83-6.95 (2H, br), 7.19-7.30 (4H, m), 7.35-7.45 (2H, m), 7.84-7.91 (2H, m), 7.91-7.79 (1H, m) , 10.70-11.00 (1H, br), 12.50-12.80 (1H, br).

Example 151
2-Chloro-4-nitro-N- [4- (4-isopropylbenzyloxymethyl) benzoyl] benzenesulfonamide
IRν (ATR) cm ^-1 ; 3320
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 1.19 (6H, d, J = 6.8 Hz), 2.86 (1H, heptet, J = 6.8 Hz), 4.47 (2H, s), 4.52 (2H, s), 7.19-7.23 (2H, m), 7.24-7.31 (4H, m), 7.84-7.88 (2H, m), 8.17 (1H, d, J = 1.7 Hz), 8.20-8.26 (2H , m).

Example 152
N- {4- [Phenyl (thiazol-2-yl) methoxymethyl] benzoyl} octane-1-sulfonamide
IRν (ATR) cm ^-1 ; 1666
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.82 (3H, t, J = 7.1 Hz), 1.17-1.30 (8H, m), 1.34-1.43 (2H, m), 1.64- 1.74 (2H, m), 3.47-3.54 (2H, m), 4.67 (1H, d, J = 13.0 Hz), 4.70 (1H, d, J = 13.0 Hz), 5.91 (1H, s), 7.31-7.36 (1H, m), 7.37-7.43 (2H, m), 7.43-7.48 (2H, m), 7.49-7.54 (2H, m), 7.72 (1H, d, J = 3.3 Hz), 7.75 (1H, d , J = 3.3 Hz), 7.90-7.95 (2H, m), 11.98-12.08 (1H, br).

Example 153
N- {2- [4- (4-Isopropylbenzyloxymethyl) phenyl] -2-oxoacetyl} octane-1-sulfonamide
IRν (ATR) cm ^-1 ; 1675
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.80-0.90 (3H, m), 1.15-1.45 (16H, m), 1.58-1.70 (2H, m), 2.83-2.95 (1H , m), 3.07-3.17 (2H, m), 4.51 (2H, s), 4.60 (2H, s), 7.20-7.32 (4H, m), 7.45-7.52 (2H, m), 7.82-7.88 (2H , m).

Example 154
4-Chloro-2-cyano-N- {2- [4- (4-isopropylbenzyloxymethyl) phenyl] -2-oxoacetyl} benzenesulfonamide
IRν (ATR) cm ^-1 ; 1739, 1677
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 1.19 (6H, d, J = 6.8 Hz), 2.83-2.95 (1H, m), 4.54 (2H, s), 4.65 (2H, s), 7.20-7.32 (4H, m), 7.55-7.62 (2H, m), 7.94-8.03 (3H, m), 8.17 (1H, d, J = 8.3 Hz), 8.55 (1H, d, J = 1.4 Hz), 12.20-13.20 (1H, br).

Example 155
6-Chloro-N- {2- [4- (4-isopropylbenzyloxymethyl) phenyl] -2-oxoacetyl} -naphthalene-2-sulfonamide
IRν (ATR) cm ^-1 ; 1671, 1606
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 1.19 (6H, d, J = 6.8 Hz), 2.88 (1H, heptet, J = 6.8 Hz), 4.50 (2H, s), 4.59 (2H, s), 7.20-7.29 (4H, m), 7.45-7.52 (2H, m), 7.67-7.75 (3H, m), 8.00 (1H, d, J = 8.8 Hz), 8.15-8.22 (1H , m), 8.22-8.26 (1H, m), 8.28-8.35 (1H, m), 8.65-8.71 (1H, m).

Example 156
N- {2- [4- (4-Isopropylbenzyloxymethyl) phenyl] -2-oxoacetyl} biphenyl-4-sulfonamide
IRν (ATR) cm ^-1 ; 1671
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 1.19 (6H, d, J = 6.8 Hz), 2.88 (1H, heptet, J = 6.8 Hz), 4.51 (2H, s), 4.60 (2H, s), 7.20-7.29 (4H, m), 7.38-7.40 (1H, br), 7.42-7.55 (5H, m), 7.71-7.78 (4H, m), 7.88-7.94 (2H, m) , 7.97-8.03 (2H, m).

Example 157
N- [4- (4-Isopropylbenzyloxymethyl) phenyl] -2- (octane-1-sulfonylamino) -2-oxoacetamide
IRν (ATR) cm ^-1 ; 1681
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.80-0.86 (3H, m), 1.15-1.33 (14H, m), 1.34-1.43 (2H, m), 1.64-1.75 (2H , m), 2.80-2.91 (1H, m), 3.37-3.48 (2H, m), 4.46 (2H, s), 4.47 (2H, s), 7.17-7.27 (4H, m), 7.29-7.36 (2H , m), 7.69-7.75 (2H, m), 10.86 (1H, s).

Example 158
N- [4- (Biphenyl-4-ylmethoxymethyl) benzoyl] naphthalene-2-sulfonamide
IRν (ATR) cm ^-1 ; 1700
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 4.58 (2H, s), 4.61 (2H, s), 7.32-7.52 (7H, m), 7.61-7.80 (6H, m), 7.82-7.92 (2H, m), 7.95 (1H, dd, J = 8.8, 2.0 Hz), 8.05 (1H, d, J = 7.8 Hz), 8.14 (1H, d, J = 8.8 Hz), 8.23 (1H , d, J = 7.8 Hz), 8.68 (1H, s), 12.40-12.80 (1H, br).

Example 159
N- [4- (2-biphenyl-4-ylethyl) benzoyl] octane-1-sulfonamide
IRν (ATR) cm ^-1 ; 1610
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.82 (3H, t, J = 7.1 Hz), 1.16-1.29 (8H, m), 1.32-1.42 (2H, m), 1.63- 1.72 (2H, m), 2.90-3.02 (4H, m), 3.46-3.53 (2H, m), 7.28-7.48 (7H, m), 7.54-7.59 (2H, m), 7.60-7.65 (2H, m ), 7.82-7.87 (2H, m), 11.92-11.98 (1H, br).

Example 160
N- [4- (3-Biphenyl-4-ylpropyl) benzoyl] octane-1-sulfonamide
IRν (ATR) cm ^-1 ; 1689
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.78-0.86 (3H, m), 1.15-1.29 (8H, m), 1.31-1.44 (2H, m), 1.62-1.73 (2H , m), 1.85-1.98 (2H, m), 2.58-2.75 (4H, m), 3.46-3.55 (2H, m), 7.25-7.38 (5H, m), 7.40-7.46 (2H, m), 7.53 -7.66 (4H, m), 7.82-7.90 (2H, m), 11.95 (1H, s).

Example 161
N- [4- (2-Pyrazol-1-ylthiazol-5-ylmethylsulfanylmethyl) benzoyl] octane-1-sulfonamide
IRν (ATR) cm ^-1 ; 1608
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.79-0.89 (3H, m), 1.16-1.30 (8H, m), 1.31-1.47 (2H, m), 1.62-1.77 (2H , m), 3.46-3.56 (2H, m), 3.83 (2H, s), 3.92 (2H, s), 6.60-6.66 (1H, m), 7.40-7.51 (3H, m), 7.84-7.95 (3H , m), 8.45-8.52 (1H, m), 11.96-12.09 (1H, br).

Example 162
N- {4- [1- (4-Isopropylbenzyl) -1H-pyrazol-4-yl] benzoyl} octane-1-sulfonamide
IRν (ATR) cm ^-1 ; 1608
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.83 (3H, t, J = 7.1 Hz), 1.15-1.29 (14H, m), 1.34-1.43 (2H, m), 1.63- 1.75 (2H, m), 2.96 (1H, heptet, J = 6.8 Hz), 3.47-3.55 (2H, m), 5.30 (2H, s), 7.19-7.28 (4H, m), 7.69-7.75 (2H, m), 7.89-7.95 (2H, m), 8.04 (1H, s), 8.44 (1H, s), 11.92-12.00 (1H, br).

Example 163
N- [4- (4- [1,3,4] thiadiazol-2-ylbenzylsulfanylmethyl) benzoyl] octane-1-sulfonamide
IRν (ATR) cm ^-1 ; 1616
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.78-0.89 (3H, m), 1.16-1.29 (8H, m), 1.30-1.40 (2H, m), 1.50-1.70 (2H , m), 3.16-3.27 (2H, m), 3.68-3.77 (4H, m), 7.28-7.35 (2H, m), 7.44-7.51 (2H, m), 7.84-7.92 (2H, m), 7.94 -8.03 (2H, m), 9.62 (1H, s), 11.90-12.11 (1H, br).

Example 164
N- [4- (3-Phenyl- [1,2,4] oxadiazol-5-ylmethylsulfanylmethyl) benzoyl] octane-1-sulfonamide
IRν (ATR) cm ^-1 ; 1668
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.78-0.87 (3H, m), 1.15-1.31 (8H, m), 1.33-1.46 (2H, m), 1.62-1.75 (2H , m), 3.45-3.53 (2H, m), 3.99 (2H, s), 4.05 (2H, s), 7.46-7.54 (2H, m), 7.54-7.63 (3H, m), 7.86-7.94 (2H , m), 7.96-8.03 (4H, m), 12.01 (1H, s).

Example 165
N- [5- (biphenyl-4-ylmethylsulfanylmethyl)-[1,2,4] oxadiazol-3-ylcarbonyl] octane-1-sulfonamide
IRν (ATR) cm ^-1 ; 1668
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.78-0.91 (3H, m), 1.15-1.41 (10H, m), 1.57-1.71 (2H, m), 3.15-3.25 (2H , m), 3.91 (2H, s), 4.00 (2H, s), 7.31-7.39 (1H, m), 7.39-7.49 (4H, m), 7.58-7.68 (4H, m).

Example 166
N- [6- (biphenyl-4-ylmethylsulfanylmethyl) pyridazin-3-ylcarbonyl] octane-1-sulfonamide
IRν (ATR) cm ^-1 ; 1581
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.79-0.86 (3H, m), 1.17-1.30 (8H, m), 1.34-1.43 (2H, m), 1.68-1.79 (2H , m), 3.46-3.54 (2H, m), 3.75 (2H, s), 4.08 (2H, s), 7.32-7.49 (5H, m), 7.56-7.67 (4H, m), 7.95 (1H, d , J = 8.5 Hz), 8.16 (1H, d, J = 8.5 Hz).

Example 167
N- [4- (Benzothiazol-2-ylmethylsulfanylmethyl) benzoyl] octane-1-sulfonamide
IRν (ATR) cm ^-1 ; 1608
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.78-0.87 (3H, m), 1.17-1.29 (8H, m), 1.35-1.43 (2H, m), 1.62-1.74 (2H , m), 3.48-3.54 (2H, m), 3.90 (2H, s), 4.14 (2H, s), 7.40-7.55 (4H, m), 7.83-7.90 (2H, m), 7.93-7.98 (1H , m), 8.05-8.11 (1H, m), 11.96-12.05 (1H, br).

Example 168
N- {4- [6- (4-Isopropylphenoxy) pyridazin-3-yl] benzoyl} octane-1-sulfonamide
IRν (ATR) cm ^-1 ; 1677
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.78-0.91 (3H, m), 1.18-1.52 (16H, m), 1.65-1.80 (2H, m), 2.95 (1H, heptet , J = 6.8 Hz), 3.48-3.58 (2H, m), 7.15-7.24 (2H, m), 7.30-7.38 (2H, m), 7.57 (1H, d, J = 9.2 Hz), 8.03-8.12 ( 2H, m), 8.18-8.27 (2H, m), 8.40 (1H, d, J = 9.2 Hz), 12.18 (1H, s).

Example 169
N- {1- [6- (4-Isopropylphenoxy) pyridazin-3-yl] -1H-pyrazole-4-carbonyl} octane-1-sulfonamide
IRν (ATR) cm ^-1 ; 1691
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.78-0.89 (3H, m), 1.16-1.48 (16H, m), 1.63-1.75 (2H, m), 2.95 (1H, heptet , J = 6.8 Hz), 3.45-3.55 (2H, m), 7.15-7.23 (2H, m), 7.32-7.40 (2H, m), 7.68 (1H, d, J = 9.3 Hz), 8.30 (1H, d, J = 9.3 Hz), 8.40 (1H, s), 9.37 (1H, s), 12.06 (1H, s).

Example 170
N- [4- (biphenyl-4-ylmethylsulfanylmethyl) benzoyl] hexane-1-sulfonamide
IRν (ATR) cm ^-1 ; 1681
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.80-0.88 (3H, m), 1.20-1.30 (4H, m), 1.34-1.45 (2H, m), 1.69 (2H, quintet , J = 7.6 Hz), 3.51 (2H, t, J = 7.6 Hz), 3.71 (2H, s), 3.77 (2H, s), 7.32-7.39 (3H, m), 7.42-7.50 (4H, m) , 7.58-7.68 (4H, m), 7.86-7.93 (2H, m), 11.97-12.07 (1H, br).

Example 171
N- [4- (biphenyl-4-ylmethylsulfanylmethyl) benzoyl] pentane-1-sulfonamide
IRν (ATR) cm ^-1 ; 1679
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.84 (3H, t, J = 7.3 Hz), 1.24-1.42 (4H, m), 1.70 (2H, quintet, J = 7.3 Hz) , 3.50 (2H, t, J = 7.3 Hz), 3.71 (2H, s), 3.77 (2H, s), 7.34-7.38 (3H, m), 7.42-7.48 (4H, m), 7.58-7.68 (4H , m), 7.86-7.92 (2H, m), 11.98-12.06 (1H, br).

Example 172
N- [4- (biphenyl-4-ylmethylsulfanylmethyl) benzoyl] butane-1-sulfonamide
IRν (ATR) cm ^-1 ; 1691
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.88 (3H, t, J = 7.3 Hz), 1.41 (2H, sextet, J = 7.3 Hz), 1.68 (2H, quintet, J = 7.8 Hz), 3.51 (2H, t, J = 7.8 Hz), 3.71 (2H, s), 3.77 (2H, s), 7.32-7.38 (3H, m), 7.42-7.48 (4H, m), 7.60- 7.67 (4H, m), 7.87-7.91 (2H, m), 11.98-12.08 (1H, br).

Example 173
N- [4- (Biphenyl-4-ylmethylsulfanylmethyl) benzoyl] hexane-1-sulfonamide sodium salt
IRν (ATR) cm ^-1 ; 1594, 1556, 1522
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.80-0.87 (3H, m), 1.16-1.36 (6H, m), 1.57 (2H, quintet, J = 7.6 Hz), 2.99- 3.07 (2H, m), 3.69 (2H, s), 3.70 (2H, s), 7.20-7.28 (2H, m), 7.32-7.40 (3H, m), 7.42-7.49 (2H, m), 7.58- 7.69 (4H, m), 7.85-7.91 (2H, m).

Example 174
N- [4- (4-Isopropylbenzylsulfanylmethyl) benzoyl] hexane-1-sulfonamide
IRν (ATR) cm ^-1 ; 1682
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.80-0.88 (3H, m), 1.18 (6H, d, J = 6.8 Hz), 1.21-1.30 (4H, m), 1.34- 1.45 (2H, m), 2.86 (1H, heptet, J = 6.8 Hz), 1.69 (2H, m), 3.51 (2H, t, J = 6.8 Hz), 3.62 (2H, s), 3.74 (2H, s ), 7.15-7.18 (4H, m), 7.39-7.44 (2H, m), 7.85-7.90 (2H, m), 11.97-12.03 (1H, br).

Example 175
N- [4- (biphenyl-4-ylmethylsulfanylmethyl) phenyl] -2- (hexane-1-sulfonylamino) -2-oxoacetamide
IRν (ATR) cm ^-1 ; 1676
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.82-0.88 (3H, m), 1.22-1.30 (4H, m), 1.36-1.44 (2H, m), 1.64-1.74 (2H , m), 3.40-3.50 (2H, m), 3.67 (2H, s), 3.70 (2H, s), 7.26-7.33 (2H, m), 7.37-7.40 (3H, m), 7.41-7.48 (2H , m), 7.58-7.73 (6H, m), 10.87-10.90 (1H, br).

Example 176
N- [4- (biphenyl-4-ylmethylsulfanylmethyl) phenyl] -2- (hexane-1-sulfonylamino) -2-oxoacetamide sodium salt
IRν (ATR) cm ^-1 ; 1680, 1612, 1585
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.81-0.90 (3H, m), 1.17-1.38 (6H, m), 1.52-1.63 (2H, m), 2.98-3.07 (2H , m), 3.65 (2H, s), 3.70 (2H, s), 7.19-7.26 (2H, m), 7.31-7.41 (3H, m), 7.41-7.49 (2H, m), 7.57-7.71 (6H , m), 9.90-9.98 (1H, br).

Example 177
N- {4- [4- (thiophen-2-yl) benzylsulfanylmethyl] benzoyl} hexane-1-sulfonamide
IRν (ATR) cm ^-1 ; 1689
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.83 (3H, t, J = 6.6 Hz), 1.18-1.30 (4H, m), 1.32-1.45 (2H, m), 1.60- 1.75 (2H, m), 3.47-3.54 (2H, m), 3.67 (2H, s), 3.74 (2H, s), 7.12 (1H, dd, J = 4.9, 3.2 Hz), 7.28-7.33 (2H, m), 7.39-7.44 (2H, m), 7.48 (1H, d, J = 3.2 Hz), 7.52 (1H, d, J = 4.9 Hz), 7.57-7.62 (2H, m), 7.86-7.91 (2H , m), 11.90-12.10 (1H, br).

Example 178
N- [5- (biphenyl-4-ylmethylsulfanylmethyl) thiophene-2-carbonyl] hexane-1-sulfonamide
IRν (ATR) cm ^-1 ; 1674
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.81-0.88 (3H, m), 1.21-1.30 (4H, m), 1.34-1.45 (2H, m), 1.70 (2H, quintet , J- = 7.3 Hz), 3.49 (2H, t, J = 7.3 Hz), 3.79 (2H, s), 3.95 (2H, s), 6.92 (1H, d, J = 3.7 Hz), 7.32-7.39 ( 3H, m), 7.42-7.47 (2H, m), 7.58-7.67 (4H, m), 7.93 (1H, d, J = 3.7 Hz), 12.00-12.18 (1H, br).

Example 179
N- [4- (4-Cyclobutylbenzylsulfanylmethyl) benzoyl] hexane-1-sulfonamide
IRν (ATR) cm ^-1 ; 1687
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.81-0.88 (3H, m), 1.21-1.30 (4H, m), 1.35-1.44 (2H, m), 1.69 (2H, quintet , J = 7.3 Hz), 1.65-1.74 (1H, m), 1.76-2.12 (3H, m), 2.22-2.31 (2H, m), 3.45-3.54 (2H, m), 3.62 (1H, s), 3.72 (1H, s), 7.14-7.21 (4H, m), 7.38-7.44 (2H, m), 7.86-7.90 (2H, m), 11.97-12.03 (1H, br).

Example 180
N- [4- (4-Ethynylbenzylsulfanylmethyl) benzoyl] hexane-1-sulfonamide
IRν (ATR) cm ^-1 ; 1684
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.80-0.88 (3H, m), 1.20-1.30 (4H, m), 1.35-1.45 (2H, m), 1.65-1.75 (2H , m), 3.51 (2H, t, J = 7.6 Hz), 3.68 (2H, s), 3.73 (2H, s), 4.16 (1H, s), 7.26-7.31 (2H, m), 7.38-7.45 ( 4H, m), 7.94-8.01 (2H, m), 11.97-12.04 (1H, br).

Example 181
[4- (Biphenyl-4-ylmethylsulfanylmethyl) -N-heptanoyl] benzenesulfonamide
IRν (ATR) cm ^-1 ; 1709
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.79 (3H, t, J = 7.1 Hz), 1.05-1.23 (6H, m), 1.34-1.45 (2H, m), 2.18 ( 2H, t, J = 7.3 Hz), 3.72 (2H, s), 3.79 (2H, s), 7.32-7.40 (3H, m), 7.42-7.50 (2H, m), 7.51-7.68 (2H, m) , 7.58-7.68 (4H, m), 7.84-7.90 (2H, m), 11.98-12.04 (1H, br).

Example 182
N- {4- [4- (thiazol-5-ylethynyl) benzylsulfanylmethyl] benzoyl} hexane-1-sulfonamide
IRν (ATR) cm ^-1 ; 1689
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.80-0.88 (3H, m), 1.21-1.30 (4H, m), 1.35-1.44 (2H, m), 1.69 (2H, quintet , J = 7.3 Hz), 3.51 (2H, t, J = 7.3 Hz), 3.71 (2H, s), 3.74 (2H, s), 7.31-7.36 (2H, m), 7.39-7.45 (2H, m) , 7.50-7.54 (2H, m), 7.86-7.92 (2H, m), 7.50-7.54 (1H, m), 7.86-7.92 (1H, m), 11.97-12.08 (1H, br).

Example 183
N- {4- [4- (pyrrol-1-yl) benzylsulfanylmethyl] benzoyl} hexane-1-sulfonamide
IRν (ATR) cm ^-1 ; 1689
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.81-0.88 (3H, m), 1.21-1.30 (4H, m), 1.35-1.44 (2H, m), 1.69 (2H, quintet , J = 7.3 Hz), 3.50 (2H, t, J = 7.3 Hz), 3.70 (2H, s), 3.76 (2H, s), 6.33-6.36 (2H, m), 7.05-7.10 (4H, m) , 7.41-7.45 (2H, m), 7.49-7.54 (2H, m), 7.87-7.92 (2H, m), 11.98-12.04 (1H, br).

Example 184
N- [4- (biphenyl-4-ylmethylsulfanylmethyl) benzoyl] -3-cyclopropylpropane-1-sulfonamide
IRν (ATR) cm ^-1 ; 1668
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); -0.03-0.04 (2H, m), 0.34-0.42 (2H, m), 0.61-0.73 (1H, m), 1.30 (2H, q, J = 7.3 Hz), 1.79 (2H, quintet, J = 7.3 Hz), 3.50-3.58 (2H, m), 3.71 (2H, s), 3.77 (2H, s), 7.32-7.39 (3H, m ), 7.41-7.47 (4H, m), 7.58-7.68 (4H, m), 7.87-7.93 (2H, m), 11.98-12.07 (1H, br).

Example 185
N- [4- (biphenyl-4-ylmethylsulfanylmethyl) phenyl] -N '-(hexyl-1-sulfonyl) urea
IRν (ATR) cm ^-1 ; 1687, 1604, 1546
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.80-0.89 (3H, m), 1.20-1.33 (4H, m), 1.33-1.46 (2H, m), 1.64-1.74 (2H , m), 3.39-3.48 (2H, m), 3.65 (2H, s), 3.69 (2H, s), 7.20-7.27 (2H, m), 7.32-7.41 (4H, m), 7.41-7.49 (3H , m), 7.58-7.69 (4H, m), 8.83 (1H, s), 9.95-10.50 (1H, br).

Example 186
4- (Biphenyl-4-ylmethylsulfanylmethyl) -N '-(hexylaminosulfonyl) benzamide
IRν (ATR) cm ^-1 ; 1687, 1604
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.77-0.84 (3H, m), 1.12-1.29 (6H, m), 1.39-1.49 (2H, m), 2.87-2.95 (2H , m), 3.71 (2H, s), 3.76 (2H, s), 7.32-7.40 (3H, m), 7.40-7.49 (4H, m), 7.58-7.68 (4H, m), 7.74-7.80 (1H , m), 7.85-7.91 (2H, m), 11.72 (1H, s).

Example 187
N- {2- [4- (biphenyl-4-ylmethylsulfanylmethyl) phenyl] -2-oxoacetyl} hexane-1-sulfonamide
IRν (ATR) cm ^-1 ; 1670
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.85-0.92 (3H, m), 1.26-1.34 (4H, m), 1.39-1.48 (2H, m), 1.68-1.74 (2H , m), 3.07-3.17 (2H, m), 3.73 (2H, s), 3.80 (2H, s), 7.20-7.32 (3H, m), 7.20-7.32 (2H, m), 7.52-7.58 (2H m), 7.20-7.32 (4H, m), 7.84-7.89 (2H, m).

Example 188
N- [4- (biphenyl-4-ylmethylsulfanylmethyl) benzoyl] -4-cyclopropylbutane-1-sulfonamide
IRν (ATR) cm ^-1 ; 1680
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); -0.04-0.02 (2H, m), 0.31-0.48 (2H, m), 0.59-0.68 (1H, m), 1.18 (2H, q, J = 7.3 Hz), 1.49 (2H, quintet, J = 7.3 Hz), 1.74 (2H, quintet, J = 7.3 Hz), 3.51 (2H, t, J = 7.3 Hz), 3.71 (2H, s) , 3.77 (2H, s), 7.32-7.39 (3H, m), 7.41-7.49 (4H, m), 7.58-7.68 (4H, m), 7.88-7.92 (2H, m), 11.98-12.07 (1H, br).

Example 189
N- [4- (biphenyl-4-ylmethoxymethyl) benzoyl] heptane-1-sulfonamide
IRν (ATR) cm ^-1 ; 1676
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.83 (3H, t, J = 7.1 Hz), 1.18-1.31 (6H, m), 1.34-1.43 (2H, m), 1.70 ( 2H, quintet, J = 7.3 Hz), 3.51 (2H, t, J = 7.3 Hz), 4.61 (2H, s), 4.65 (2H, s), 7.33-7.40 (1H, m), 7.43-7.55 (6H , m), 7.63-7.70 (4H, m), 7.90-7.96 (2H, m), 12.00-12.08 (1H, br).

Example 190
N- [4- (Biphenyl-4-ylmethoxymethyl) benzoyl] -5-cyclopropylpentane-1-sulfonamide
IRν (ATR) cm ^-1 ; 1676
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); -0.08--0.01 (2H, m), 0.30-0.38 (2H, m), 0.56-0.68 (1H, m), 1.13 (2H , q, J = 7.1 Hz), 1.30-1.47 (4H, m), 3.52 (2H, t, J = 7.3 Hz), 4.62 (2H, s), 4.65 (2H, s), 7.33-7.39 (1H, m), 7.43-7.55 (6H, m), 7.64-7.70 (4H, m), 7.90-7.97 (2H, m), 12.00-12.08 (1H, br).

The compounds of Examples 191 to 229 were produced in the same manner as in Examples 34 to 53.

Example 191
4 '-[4- (2,4-Dichlorobenzenesulfonylaminocarbonyl) benzyloxymethyl] biphenyl-4-carboxylic acid
IRν (ATR) cm ^-1 ; 1687
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 4.57 (2H, s), 4.58 (2H, s), 7.28-7.33 (2H, m), 7.46 (1H, dd, J = 8.3 , 2.0 Hz), 7.45-7.50 (2H, m), 7.51 (1H, d, J = 2.0 Hz), 7.69-7.74 (2H, m), 7.76-7.81 (2H, m), 7.85-7.90 (2H, m), 7.98 (1H, d, J = 8.3 Hz), 8.00-8.05 (2H, m), 8.60 (1H, br), 8.82 (1H, br).

Example 192
N- [4- (9H-Fluoren-9-yloxymethyl) benzoyl] naphthalene-2-sulfonamide
IRν (ATR) cm ^-1 ; 1693
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 4.45 (2H, s), 5.73 (1H, s), 7.29-7.36 (2H, m), 7.39-7.48 (4H, m), 7.61-7.77 (4H, m), 7.78-7.87 (4H, m), 7.94 (1H, dd, J = 8.5, 1.7 Hz), 8.04 (1H, d, J = 8.0 Hz), 8.13 (1H, d, J = 8.5 Hz), 8.22 (1H, d, J = 8.0 Hz), 8.64-8.70 (1H, m), 12.5-12.7 (1H, br).

Example 193
N- [4- (4'-Cyclopentyloxy) biphenylcarbonyl] naphthalene-2-sulfonamide
IRν (ATR) cm ^-1 ; 1685, 1600
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 1.50-1.80 (6H, m), 1.85-2.00 (2H, m), 4.82-4.92 (1H, m), 6.95-7.05 (2H , m), 7.62-7.80 (6H, m), 7.86-8.02 (3H, m), 8.06 (1H, d, J = 7.8 Hz), 8.16 (1H, d, J = 8.8 Hz), 8.25 (1H, d, J = 7.8 Hz), 8.69 (1H, s), 12.50-12.70 (1H, br).

Example 194
N- [1- (biphenyl-4-ylmethyl) -1H-pyrrol-3-ylcarbonyl] hexane-1-sulfonamide
IRν (ATR) cm ^-1 ; 1633
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.79-0.86 (3H, m), 1.20-1.28 (4H, m), 1.34-1.42 (2H, m), 1.60-1.71 (2H , m), 3.43 (2H, t, J = 8.0 Hz), 5.19 (2H, s), 6.61-6.63 (1H, m), 6.93-6.95 (1H, m), 7.18-7.24 (2H, m), 7.32-7.39 (1H, m), 7.42-7.48 (2H, m), 7.61-7.67 (4H, m), 7.72-7.75 (1H, m), 11.28-11.32 (1H, br).

Example 195
N-{[4- (biphenyl-4-ylmethyl) methylamino] methyl} benzoyl) hexane-1-sulfonamide The above compound is a reductive alkylation of methyl 4- (aminomethyl) benzoate hydrochloride and 4-phenylbenzaldehyde, Subsequently, after methylating with methyl iodide, it manufactured by the method similar to Example 33.
IRν (ATR) cm ^-1 ; 1593
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.78-0.87 (3H, m), 1.18-1.28 (4H, m), 1.30-1.42 (2H, m), 1.62-1.72 (2H , m), 2.19 (3H, s), 3.42 (2H, t, J = 7.6 Hz), 3.70 (2H, s), 3.73 (2H, s), 7.31-7.38 (1H, m), 7.41-7.53 ( 6H, m), 7.62-7.69 (4H, m), 7.89-7.95 (2H, m), 11.30-12.02 (1H, br).

Example 196
N- [4- (5-Phenylpyridin-2-ylmethylsulfanylmethyl) benzoyl] hexane-1-sulfonamide
IRν (ATR) cm ^-1 ; 1680
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.78-0.87 (3H, m), 1.18-1.28 (4H, m), 1.32-1.44 (2H, m), 1.60-1.73 (2H , m), 3.45-3.53 (2H, m), 3.78 (2H, s), 3.73 (2H, s), 7.38-7.54 (3H, m), 7.66-7.74 (2H, m), 7.83-7.92 (2H , m), 7.97-8.07 (1H, m), 8.75-8.81 (1H, m), 11.90-12.10 (1H, br).

Example 197
N- [6- (Biphenyl-4-ylmethylsulfanylmethyl) pyridin-3-ylcarbonyl] hexane-1-sulfonamide
IRν (ATR) cm ^-1 ; 1695
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.80-0.87 (3H, m), 1.20-1.30 (4H, m), 1.34-1.45 (2H, m), 1.65-1.76 (2H , m), 3.45-3.53 (2H, m), 3.78 (2H, s), 3.85 (2H, s), 7.30-7.69 (5H, m), 7.30-7.69 (1H, d, J = 8.1Hz), 7.57-7.68 (4H, m), 8.22 (1H, dd, J = 8.1, 1.7 Hz), 8.96-9.01 (1H, m), 13.22-13.38 (1H, br).

Example 198
N- {4- [4- (Pyridin-2-yl) benzylsulfanylmethyl] benzoyl} hexane-1-sulfonamide
IRν (ATR) cm ^-1 ; 1680
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.78-0.87 (3H, m), 1.18-1.28 (4H, m), 1.32-1.44 (2H, m), 1.62-1.73 (2H , m), 3.50 (2H, t, J = 7.6 Hz), 3.72 (2H, s), 3.76 (2H, s), 7.30-7.36 (1H, m), 7.36-7.47 (4H, m), 7.82- 7.97 (4H, m), 8.00-8.06 (2H, m), 8.64 (1H, d, J = 3.9 Hz), 11.92-12.10 (1H, br).

Example 199
N- [4- (4-Phenoxybenzylsulfanylmethyl) benzoyl] hexane-1-sulfonamide
IRν (ATR) cm ^-1 ; 1678
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.80-0.88 (3H, m), 1.20-1.30 (4H, m), 1.34-1.44 (2H, m), 1.69 (2H, quintet , J = 7.8 Hz), 3.50 (2H, t, J = 7.8 Hz), 3.66 (2H, s), 3.76 (2H, s), 6.90-6.96 (2H, m), 6.97-7.02 (2H, m) , 7.10-7.16 (1H, m), 7.24-7.31 (2H, m), 7.35-7.45 (4H, m), 7.86-7.91 (2H, m), 11.97-12.03 (1H, br).

Example 200
N- [4- (1-Ethyl-2,3-dihydro-1H-indol-5-ylmethylsulfanylmethyl) benzoyl] hexane-1-sulfonamide
IRν (ATR) cm ^-1 ; 1676
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.83-0.91 (3H, m), 1.09 (3H, t, J = 7.1 Hz), 1.24-1.34 (4H, m), 1.36- 1.48 (2H, m), 1.52-1.68 (2H, m), 2.83 (2H, t, J = 8.2 Hz), 3.03-3.14 (4H, m), 3.26 (2H, t, J = 8.2 Hz), 3.54 , 3.71 (2H, 2H, s, s), 6.40 (1H, d, J = 7.0 Hz), 6.83-6.88 (1H, m), 6.90-6.94 (1H, m), 7.39-7.46 (2H, m) , 7.82-7.88 (2H, m), 11.08 (1H, s).

Example 201
N- {4- [4- (2H- [1,2,3] -Triazol-4-yl) benzylsulfanylmethyl] benzoyl} hexane-1-sulfonamide
IRν (ATR) cm ^-1 ; 1685
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.81-0.87 (3H, m), 1.21-1.30 (4H, m), 1.34-1.45 (2H, m), 1.65-1.74 (2H , m), 3.50 (2H, d, J = 7.7 Hz), 3.70, 3.75 (2H, 2H, s, s), 7.32-7.39 (2H, m), 7.71-7.47 (2H, m), 7.77-7.84 (2H, m), 7.86-7.91 (2H, m), 8.18-8.27 (1H, br), 11.96-12.04 (1H, br).

Example 202
N- [4- (3'-Methoxybiphenyl-4-ylmethylsulfanylmethyl) benzoyl] hexane-1-sulfonamide
IRν (ATR) cm ^-1 ; 1685
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.81-0.87 (3H, m), 1.21-1.28 (4H, m), 1.35-1.44 (2H, m), 1.65-1.72 (2H , m), 3.47-3.54 (2H, m), 3.71 (2H, s), 3.77 (2H, s), 3.82 (3H, s), 6.90-6.96 (1H, m), 7.15-7.19 (1H, m ), 7.19-7.23 (1H, m), 7.33-7.39 (3H, m), 7.42-7.46 (2H, m), 7.59-7.63 (2H, m), 7.87-7.91 (2H, m), 11.96-12.05 (1H, br).

Example 203
N- [4- (4'-Methoxybiphenyl-4-ylmethylsulfanylmethyl) benzoyl] hexane-1-sulfonamide
IRν (ATR) cm ^-1 ; 1689, 1606
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.78-0.87 (3H, m), 1.16-1.30,
(4H, m), 1.33-1.45 (2H, m), 1.61-1.75 (2H, m), 3.46-3.53 (2H, m), 3.68 (2H, s), 3.75 (2H, s), 6.99-7.01 (2H, m), 7.31-7.33 (2H, m), 7.42-7.44 (2H, m), 7.54-7.59 (4H, m), 7.87-7.89 (2H, m), 11.95-12.05 (1H, br) .

Example 204
N- {4- [3 '-(trifluoromethyl) biphenyl-4-ylmethylsulfanylmethyl] benzoyl} hexane-1-sulfonamide
IRν (ATR) cm ^-1 ; 1670
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.81-0.87 (3H, m), 1.21-1.28 (4H, m), 1.35-1.44 (2H, m), 1.65-1.75 (2H , m), 3.48-3.55 (2H, m), 3.73 (2H, s), 3.77 (2H, s), 7.38-7.47 (4H, m), 7.67-7.73 (4H, m), 7.88-7.92 (2H , m), 7.93-7.99 (2H, m), 11.97-12.04 (1H, br).

Example 205
N- [4- (3'-Cyanobiphenyl-4-ylmethylsulfanylmethyl) benzoyl] hexane-1-sulfonamide
IRν (ATR) cm ^-1 ; 1660
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.81-0.87 (3H, m), 1.22-1.28 (4H, m), 1.35-1.45 (2H, m), 1.65-1.74 (2H , m), 3.47-3.53 (2H, m), 3.73 (2H, s), 3.77 (2H, s), 7.38-7.47 (4H, m), 7.66 (1H, t, J = 7.8 Hz), 7.68- 7.72 (2H, m), 7.79-7.84 (1H, m), 7.88-7.92 (2H, m), 7.99-8.04 (1H, m), 8.14-8.16 (1H, m), 11.97-12.04 (1H, br ).

Example 206
N- [4- (2'-Methoxybiphenyl-4-ylmethylsulfanylmethyl) benzoyl] hexane-1-sulfonamide
IRν (ATR) cm ^-1 ; 1685
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.81-0.87 (3H, m), 1.22-1.28 (4H, m), 1.35-1.44 (2H, m), 1.69 (2H, quintet , J = 7.8 Hz), 3.50 (2H, t, J = 7.8 Hz), 3.70 (2H, s), 3.76 (3H, s), 3.79 (2H, s), 6.98-7.05 (1H, m), 7.08 -7.13 (1H, m), 7.25-7.36 (4H, m), 7.39-7.47 (4H, m), 7.88-7.94 (2H, m), 11.98-12.04 (1H, br).

Example 207
N- {4- [4- (2,3-Dihydrobenzofuran-6-yl) benzylsulfanylmethyl] benzoyl} hexane-1-sulfonamide
IRν (ATR) cm ^-1 ; 1674
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.80-0.86 (3H, m), 1.20-1.28 (4H, m), 1.34-1.45 (2H, m), 1.69 (2H, quintet , J = 7.3 Hz), 3.20 (2H, s), 3.51 (2H, t, J = 7.3 Hz), 3.69 (2H, s), 3.76 (2H, s), 4.56 (2H, s), 7.01-7.05 (1H, m), 7.08-7.13 (1H, m), 7.26-7.36 (3H, m), 7.41-7.47 (2H, m), 7.53-7.58 (2H, m), 7.41-7.47 (2H, m) , 11.98-12.04 (1H, br).

Example 208
N- {4- [4- (1,4-Benzodioxane-6-yl) benzylsulfanylmethyl] benzoyl} hexane-1-sulfonamide
IRν (ATR) cm ^-1 ; 1664
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.81-0.88 (3H, m), 1.21-1.308 (4H, m), 1.35-1.45 (2H, m), 1.65-1.74 (2H , m), 3.46-3.53 (2H, m), 3.68 (2H, s), 3.76 (2H, s), 4.27 (4H, s), 6.91 (1H, d, J = 8.3 Hz), 7.09-7.15 ( 2H, m), 7.29-7.34 (2H, m), 7.41-7.46 (2H, m), 7.50-7.55 (2H, m), 7.86-7.91 (2H, m), 11.96-12.04 (1H, br).

Example 209
N- {4- [3 '-(trifluoromethyl) biphenyl-4-ylmethoxymethyl] benzoyl} hexane-1-sulfonamide
IRν (ATR) cm ^-1 ; 1680
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.80-0.90 (3H, m), 1.20-1.30 (4H, m), 1.33-1.45 (2H, m), 1.70 (2H, quintet , J = 7.6 Hz), 3.51 (2H, t, J = 7.6 Hz), 4.64 (2H, s), 4.66 (2H, s), 7.47-7.55 (4H, m), 7.67-7.78 (4H, m) , 7.90-8.03 (4H, m), 12.00-12.07 (1H, br).

Example 210
N- [4- (3'-Nitrobiphenyl-4-ylmethylsulfanylmethyl) -benzoyl] hexane-1-sulfonamide
IRν (ATR) cm ^-1 ; 1680
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.80-0.89 (3H, m), 1.20-1.30 (4H, m), 1.33-1.45 (2H, m), 1.63-1.74 (2H , m), 3.45-3.55 (2H, m), 3.74 (2H, s), 3.88 (2H, s), 7.40-7.49 (4H, m), 7.71-7.80 (3H, m), 7.85-7.93 (2H , m), 8.12-8.16 (1H, m), 8.18-8.25 (1H, m), 8.43 (1H, s), 11.70-12.70 (1H, br).

Example 211
N- {4- [3- (trifluoromethyl) benzylsulfanylmethyl] benzoyl} hexane-1-sulfonamide
IRν (ATR) cm ^-1 ; 1682
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.81-0.88 (3H, m), 1.21-1.30 (4H, m), 1.34-1.45 (2H, m), 1.63-1.75 (2H , m), 3.46-3.54 (2H, m), 3.76 (2H, s), 3.79 (2H, s), 7.34-7.39 (2H, m), 7.40-7.46 (2H, m), 7.48-7.52 (2H , m), 8.03-8.08 (2H, m), 11.94-12.02 (1H, br).

Example 212
N-{[4- (3'-Methoxybiphenyl-4-ylmethylsulfanylmethyl) phenyl] -2-oxoacetyl} hexane-1-sulfonamide
IRν (ATR) cm ^-1 ; 1684
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.83-0.92 (3H, m), 1.25-1.34 (4H, m), 1.38-1.48 (2H, m), 1.73 (2H, quintet , J = 7.3 Hz), 3.53 (2H, t, J = 7.3 Hz), 3.72 (2H, s), 3.79-3.83 (5H, m), 6.89-6.95 (1H, m), 7.15-7.19 (1H, m), 7.20-7.24 (1H, m), 7.36-7.40 (3H, m), 7.67-7.78 (2H, m), 7.90-8.03 (2H, m), 7.84-7.90 (2H, m).

Example 213
(E)-({4- [3 '-(trifluoromethyl) biphenyl-4-yl] methyleneaminooxy} benzoyl) hexane-1-sulfonamide
IRν (ATR) cm ^-1 ; 1654
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.80-0.89 (3H, m), 1.20-1.31 (4H, m), 1.35-1.47 (2H, m), 1.72 (2H, quintet , J = 7.3 Hz), 3.51 (2H, t, J = 7.3 Hz), 7.37-7.43 (2H, m), 7.47-7.55 (2H, m), 7.89-8.10 (8H, m), 8.87 (1H, s), 11.92-11.99 (1H, br).

Example 214
N- (4- {4- [3- (trifluoromethyl) isoxazol-5-yl] benzylsulfanylmethyl} benzoyl) hexane-1-sulfonamide
IRν (ATR) cm ^-1 ; 1683
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.80-0.88 (3H, m), 1.20-1.30 (4H, m), 1.33-1.45 (2H, m), 1.64-1.75 (2H , m), 3.45-3.55 (2H, m), 3.76 (2H, s), 3.77 (2H, s), 7.40-7.46 (2H, m), 7.46-7.52 (2H, m), 7.70 (1H, s ), 7.85-7.95 (4H, m), 11.60-12.40 (1H, br).

Example 215
N- [4- (3'-Methoxybiphenyl-4-ylmethoxymethyl) benzoyl] hexane-1-sulfonamide
IRν (ATR) cm ^-1 ; 1682
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.81-0.88 (3H, m), 1.21-1.31 (4H, m), 1.35-1.45 (2H, m), 1.65-1.74 (2H , m), 3.48-3.54 (2H, m), 3.82 (3H, s), 4.61 (2H, s), 4.65 (2H, s), 6.91-6.97 (1H, m), 7.17-7.20 (1H, m ), 7.21-7.26 (1H, m), 7.36-7.40 (1H, m), 7.45-7.49 (2H, m), 7.49-7.54 (2H, m), 7.65-7.69 (2H, m), 7.91-7.97 (2H, m), 11.99-12.08 (1H, br).

Example 216
N- [4- (3'-Methoxybiphenyl-3-ylmethylsulfanylmethyl) benzoyl] hexane-1-sulfonamide
IRν (ATR) cm ^-1 ; 1685
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.81-0.87 (3H, m), 1.21-1.29 (4H, m), 1.34-1.44 (2H, m), 1.64-1.74 (2H , m), 3.47-3.54 (2H, m), 3.75 (2H, s), 3.78 (2H, s), 3.82 (3H, s), 6.91-6.97 (1H, m), 7.14-7.16 (1H, m ), 7.16-7.21 (1H, m), 7.25-7.30 (1H, m), 7.35-7.46 (4H, m), 7.51-7.57 (2H, m), 7.86-7.90 (2H, m), 11.95-12.03 (1H, br).

Example 217
N- [4- (Benzoxazol-6-ylmethylsulfanylmethyl) benzoyl} hexane-1-sulfonamide
IRν (ATR) cm ^-1 ; 1703
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.80-0.88 (3H, m), 1.20-1.30 (4H, m), 1.35-1.44 (2H, m), 1.69 (2H, quintet , J = 7.3 Hz), 3.50 (2H, t, J = 7.3 Hz), 3.75 (2H, s), 3.81 (2H, s), 7.35-7.38 (1H, m), 7.39-7.44 (4H, m) , 7.67-7.73 (2H, m), 7.85-7.90 (4H, m), 8.71 (1H, s), 11.97-12.03 (1H, br).

Example 218
N- [4- (3'-Dimethylaminobiphenyl-4-ylmethylsulfanylmethyl) benzoyl] hexane-1-sulfonamide
IRν (ATR) cm ^-1 ; 1653
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.81-0.87 (3H, m), 1.21-1.29 (4H, m), 1.34-1.45 (2H, m), 1.64-1.75 (2H , m), 2.95 (6H, s), 3.46-3.52 (2H, m), 3.70 (2H, s), 3.76 (2H, s), 6.70-6.74 (1H, m), 6.87-6.92 (2H, m ), 7.21-7.27 (1H, m), 7.31-7.36 (2H, m), 7.42-7.46 (2H, m), 7.55-7.60 (2H, m), 7.87-7.92 (2H, m), 11.95-12.03 (1H, br).

Example 219
N- [4- (Biphenyl-4-ylmethylsulfanylmethyl) benzoyl] -3- (3-methyl- [1,2,4] oxadiazol-5-yl) propane-1-sulfonamide
IRν (ATR) cm ^-1 ; 1660
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 2.12-2.23 (2H, m), 2.27 (3H, s), 3.08 (2H, t, J = 7.6 Hz), 3.60-3.69 ( 2H, m), 3.70 (2H, s), 3.76 (2H, s), 7.31-7.38 (3H, m), 7.42-7.47 (4H, m), 7.58-7.67 (4H, m), 7.86-7.92 ( 2H, m), 12.00-12.15 (1H, br).

Example 220
N-({4- [4- (1,4-Benzodioxane-6-yl) benzylsulfanylmethyl] phenyl} -2-oxoacetyl) hexane-1-sulfonamide
IRν (ATR) cm ^-1 ; 1674
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.82-0.90 (3H, m), 1.24-1.32 (4H, m), 1.37-1.47 (2H, m), 1.67-1.77 (2H , m), 3.47-3.54 (2H, m), 3.69 (2H, s), 3.78 (2H, s), 4.26 (4H, s), 6.91 (1H, d, J = 7.3 Hz), 7.08-7.14 ( 2H, m), 7.28-7.34 (2H, m), 7.50-7.56 (4H, m), 7.83-7.89 (2H, m).

Example 221
(E) -N-({4- [4- (1,4-Benzodioxane-6-yl) phenyl] methyleneaminooxy} benzoyl) hexane-1-sulfonamide
IRν (ATR) cm ^-1 ; 1581
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.81-0.90 (3H, m), 1.20-1.30 (4H, m), 1.37-1.48 (2H, m), 1.70 (2H, quintet , J = 7.3 Hz), 3.47-3.54 (2H, m), 4.29 (4H, s), 6.96 (1H, d, J = 7.3 Hz), 7.20-7.26 (2H, m), 7.35-7.42 (2H, m), 7.72-7.77 (2H, m), 7.83-7.89 (2H, m), 7.97-8.03 (2H, m), 8.81 (1H, s), 11.93-11.97 (1H, br).

Example 222
(E) -N- [4- (Biphenyl-4-yl) methyleneaminooxy) benzoyl] hexane-1-sulfonamide
IRν (ATR) cm ^-1 ; 1668
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.81-0.88 (3H, m), 1.21-1.32 (4H, m), 1.34-1.45 (2H, m), 1.65-1.75 (2H , m), 3.47-3.54 (2H, m), 7.35-7.44 (3H, m), 7.45-7.53 (2H, m), 7.70-7.75 (2H, m), 7.78-7.83 (2H, m), 7.89 -7.94 (2H, m), 7.97-8.03 (2H, m), 8.82 (1H, s), 11.88-11.94 (1H, br).

Example 223
(E) -N-{[4- (3'-Nitrobiphenyl-4-yl) methyleneaminooxy] benzoyl} hexane-1-sulfonamide
IRν (ATR) cm ^-1 ; 1662
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.81-0.87 (3H, m), 1.21-1.30 (4H, m), 1.36-1.45 (2H, m), 1.66-1.75 (2H , m), 3.48-3.54 (2H, m), 7.37-7.42 (2H, m), 7.78-7.83 (1H, m), 7.92-8.03 (6H, m), 8.20-8.28 (2H, m), 8.50 -8.52 (1H, m), 8.87 (1H, s), 11.90-11.95 (1H, br).

Example 224
N- {4- [4- (1,4-Benzodioxane-6-yl) benzyloxymethyl] benzoyl} hexane-1-sulfonamide
IRν (ATR) cm ^-1 ; 1701
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.80-0.87 (3H, m), 1.21-1.30 (4H, m), 1.34-1.44 (2H, m), 1.65-1.74 (2H , m), 3.46-3.53 (2H, m), 4.27 (4H, s), 4.58 (2H, s), 4.63 (2H, s), 6.89-6.93 (1H, m), 7.10-7.15 (2H, m ), 7.37-7.43 (2H, m), 7.47-7.52 (2H, m), 7.55-7.60 (2H, m), 7.90-7.94 (2H, m), 11.98-12.07 (1H, br).

Example 225
(E) -N- [4- (3'-Dimethylaminobiphenyl-4-ylmethyleneaminooxy) benzoyl] hexane-1-sulfonamide
IRν (ATR) cm ^-1 ; 1684
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.80-0.91 (3H, m), 1.20-1.31 (4H, m), 1.33-1.46 (2H, m), 1.65-1.76 (2H , m), 2.98 (6H, s), 3.47-3.53 (2H, m), 6.74-6.83 (1H, m), 6.94-7.04 (2H, m), 7.25-7.32 (1H, m), 7.35-7.41 (2H, m), 7.75-7.81 (2H, m), 7.86-7.92 (2H, m), 7.97-8.03 (2H, m), 8.82 (1H, s), 11.86-12.00 (1H, br).

Example 226
N- [4- (3-Methoxybiphenyl-4-ylmethylsulfanylmethyl) benzoyl] hexane-1-sulfonamide
IRν (ATR) cm ^-1 ; 1683
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.80-0.88 (3H, m), 1.20-1.32 (4H, m), 1.34-1.46 (2H, m), 1.65-1.75 (2H , m), 3.46-3.55 (2H, m), 3.67 (2H, s), 3.80 (2H, s), 3.88 (3H, s), 7.15-7.24 (2H, m), 7.25-7.30 (1H, m ), 7.35-7.40 (1H, m), 7.43-7.50 (4H, m), 7.65-7.72 (2H, m), 7.86-7.93 (2H, m), 11.95-12.05 (1H, br).

Example 227
(E) -N- [4- (3'-Methoxybiphenyl-4-ylmethyleneaminooxy) benzoyl] hexane-1-sulfonamide
IRν (ATR) cm ^-1 ; 3274, 1679
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.85 (3H, t, J = 6.8 Hz), 1.22-1.30 (4H, m), 1.35-1.45 (2H, m), 1.66- 1.75 (2H, m), 3.47-3.55 (2H, m), 3.84 (3H, s), 6.98 (1H, dd, J = 8.3, 2.0 Hz), 7.25-7.31 (2H, m), 7.37-7.43 ( 3H, m), 7.81-7.83 (2H, m), 7.90-7.92 (2H, m), 7.99-8.01 (2H, m), 8.83 (1H, s), 11.90-11.95 (1H, br).

Example 228
N-({4- [4- (1,3-benzodioxol-5-yl) benzylsulfanylmethyl] phenyl} -2-oxoacetyl) hexane-1-sulfonamide
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.80-0.91 (3H, m), 1.22-1.34 (4H, m), 1.35-1.50 (2H, m), 1.65-1.80 (2H , m), 3.45-3.55 (2H, m), 3.69 (2H, s), 3.78 (2H, s), 5.60 (2H, s), 6.83-6.91 (1H, m), 7.00-7.10 (2H, m ), 7.26-7.35 (2H, m), 7.48-7.58 (4H, m), 7.80-7.90 (2H, m).

Example 229
N-({4- [4- (3 ', 4'-Dimethoxybiphenyl-4-ylmethylsulfanylmethyl] phenyl} -2-oxoacetyl) hexane-1-sulfonamide
¹ H-NMR (DMSO-d ₆ , 400 MHz) δ (ppm); 0.82-0.91 (3H, m), 1.24-1.32 (4H, m), 1.39-1.48 (2H, m), 1.68-1.78 (2H , m), 3.46-3.54 (2H, m), 3.70 (2H, s), 3.79 (2H, s), 3.95 (3H, s), 3.97 (3H, s), 6.89-6.94 (1H, m), 7.09-7.15 (2H, m), 7.29-7.34 (2H, m), 7.51-7.58 (4H, m), 7.85-7.90 (2H, m).

The structural formulas of the above Example compounds are shown in Tables 1 to 12 below.

Test Example 1 Measurement of PTP-1B Inhibitory Activity PTP-1B inhibitory activity was measured using recombinant human PTP-1B as an enzyme and p-nitrophenyl phosphate (pNPP) as a substrate. A 100% DMSO stock solution of the test compound was prepared and 2 μL was added to each well of a 96-well plate. Next, assay buffer (100 mM HEPES (pH 7.2), 1 mM EDTA, 1 mM DTT) (170 μL) and PTP-1B enzyme solution (10 μL) were added to each well and incubated at 37 ° C. for 10 minutes. Thereafter, 30 mM pNPP (20 μL) was added and incubated at 37 ° C. for 30 minutes. 1 N NaOH (100 μL) was added and the absorbance at 405 nm was measured. The absorbance at the time of no addition of the test compound was taken as 100%, and the concentration of the compound that suppresses the enzyme activity by 50% (IC ₅₀ value) was calculated. The results are shown in Table 13.

Test Example 2 Pharmacological Action of Example Compound in db / db Mice (Test Method)
Allocate 8-7-year-old male db / db mice to the control group and the 30 mg / kg / day administration group of the test compound as 6 to 7 animals per group so that the average values of body weight, plasma glucose and triglyceride are almost equal. It was. The test compound was suspended in 0.5% methylcellulose solution and orally administered daily for 4 weeks. In the control group, only 0.5% methylcellulose solution was orally administered. Four weeks after administration, blood was collected from the tail vein under non-fasting conditions, and glucose and triglycerides in plasma were measured using a commercially available measurement kit (glucose CII-Test Wako and triglyceride G-Test Wako, manufactured by Wako Pure Chemical Industries, Ltd.). The rate of decrease in plasma glucose and triglycerides was determined from the following equation.
Decrease rate (%) = [(average value of control group−average value of test compound administration group) / average value of control group] × 100
(result)
The compounds of Examples 122, 170, and 175 were 31.1%, 24.1%, and 29.1% plasma glucose, and triglyceride plasma, respectively, by repeated oral administration at 30 mg / kg / day for 4 weeks. 41.0%, 56.7% and 58.9%.

Test Example 3 Pharmacological Action of Example Compound in High Fat Diet Induced Obese Mice (Test Method)
High-fat diet was given to 5-week-old male C57 / 6J mice for 4-6 weeks to create obese model mice. Before the start of the test, each group was assigned to the control group and the 30 mg / kg / day administration group of the test compound as 6 to 7 animals so that the average body weight and the average value of plasma triglyceride were approximately equal. The test compound was suspended in 0.5% methylcellulose solution and orally administered every day. In the control group, only 0.5% methylcellulose solution was orally administered. Two or four weeks after administration, blood was collected from the tail vein under non-fasting conditions, and triglycerides in plasma were measured using a commercially available measurement kit (Triglyceride G-Test Wako, manufactured by Wako Pure Chemical Industries). The amount of weight gain during the administration period was calculated, and the rate of decrease in plasma triglycerides was determined from the following formula.
Decrease rate (%) = [(average value of control group−average value of test compound administration group) / average value of control group] × 100
(result)
The compound of Example 46 reduced body weight gain by 68.8% and plasma triglyceride by 18.7% by repeated oral administration at 30 mg / kg / day for 2 weeks. The compound of Example 170 reduced body weight gain by 14.5% and plasma triglyceride by 34.4% after repeated oral administration at 30 mg / kg / day for 4 weeks.

Test Example 4 Blood Level after Oral Administration Male test rats (7 weeks old) were forcibly orally administered 10 mg / kg of the test compound suspended in a 0.5% methylcellulose solution. Blood was collected from the jugular vein using 1 mL syringes with heparin added at 0.25, 0.5, 1, 3, 5, 8 and 24 hours after administration. The plasma drug concentration was measured using HPLC to determine the maximum blood concentration.
The compounds of Examples 46, 54, 83, 122, 138, 157, 170, 175 and 187-190 exhibited a maximum blood concentration of 1-20 μg / mL.

Test Example 5 Insulin Receptor Phosphorylation Test (In Vitro)
(Test method)
HepG2 cells are seeded at a cell density of 2 × 10 ⁶ cells / 2 mL / well in a DMEM medium solution containing 10% fetal bovine serum in a 6-well plate, and cultured at 37 ° C. under 5% CO ₂ conditions for 24 hours. did. Subsequently, it was replaced with fetal bovine serum free DMEM medium and starved for 6 hours. Each test compound was added and 1 nM insulin was added after 1 hour incubation. After 10 minutes from the addition of insulin, the cells were washed with Tris buffer (pH 7.5), and a sample collection buffer (20 mM Tris-HCl (pH 7.5), 5 mM EDTA-2Na, 10 mM Sodium fluoride, 10 mM Sodium pyrophosphate, 1 mM Sodium orthovanadate, 1 μg / mL p-Amidinophenyl methanol fluoride, 1 μg / mL Leupeptin, 1 μg / mL Antipain, 1 μg / mL Benzymidine). The protein concentration was measured, mixed with the SDS treatment buffer so as to have the same protein concentration, and incubated at 100 ° C. for 10 minutes. The cell lysate was run on a 7.5% SDS polyacrylamide gel and transferred to a nitrocellulose membrane. Phospho Detect Anti-Insulin Receptor (pTyr 1162/1163) as Rabbit pAb or Insulin Rβ Antibody (C-19) as primary antibody, Anti-Rabbit IgG HRP-linked antigen as secondary antibody Used to emit light. The amount of luminescence was detected with Chemi Doc XRS Plus.
(result)
The compounds of Examples 20, 46, 53, 83, 94, 122, 138 and 170 increased phosphorylation of the insulin receptor by more than 50% at 10 μM.

The present invention relates to an antihyperglycemic agent, an antihyperlipidemic agent, an insulin resistance improving agent, a diabetes therapeutic agent, a diabetic complication therapeutic agent, a glucose intolerance improving agent, an antiarteriosclerosis agent, an antiobesity agent, an anti-obesity agent, It is useful as an inflammatory agent, a prophylactic / therapeutic agent for diseases mediated by PTP-1B and a prophylactic / therapeutic agent for metabolic syndrome. Moreover, since the pharmaceutical which contains this invention compound as an active ingredient has few side effects, it can become a highly safe therapeutic agent for diabetes.

This application is based on Japanese Patent Application No. 2013-021833 filed in Japan, the contents of which are incorporated in full herein.

Claims

Formula (I):

{Where,
A represents an optionally substituted carbocyclic group, an optionally substituted biaryl, or an optionally substituted heterocyclic group;
B represents an optionally substituted divalent carbocyclic group, an optionally substituted biarylene, or an optionally substituted divalent heterocyclic group;
C is an optionally substituted carbocyclic group, an optionally substituted biaryl, an optionally substituted arylalkyl, an optionally substituted arylalkenyl, an optionally substituted alkyl, a substituted An optionally substituted alkenyl, an optionally substituted cycloalkyl, an optionally substituted cycloalkylalkyl, an optionally substituted heterocyclic group, or an optionally substituted heterocyclic alkenyl;
X is an optionally substituted alkylene, an optionally substituted alkenylene, an optionally substituted alkynylene, an optionally substituted * — (CH 2 ) m —O— (CH 2 ) n — * *, Optionally substituted * — (CH 2 ) m —S (O) p — (CH 2 ) n — **, optionally substituted * — (CH 2 ) m —N (R 1 ) — (CH 2 ) n — **, optionally substituted * — (CH 2 ) m —CO— (CH 2 ) n — **, optionally substituted * — (CH 2 ) q —CO —N (R 1 ) — (CH 2 ) r — **, optionally substituted * — (CH 2 ) q —N (R 1 ) —CO— (CH 2 ) r — **, substituted and may be * - (CH 2) q -SO 2 -N (R 1) - (CH 2) r - **, substituted * - (CH 2) q -N (R 1) -SO 2 - (CH 2) r - **, * - C (R 1) = N-O - **, or * -O-N = C ( R 1 )-** (wherein m, n, q and r each independently represents 0 or an integer of 1 to 4, p represents 0, 1 or 2; R 1 represents hydrogen; Represents an atom or lower alkyl, * represents a bonding position to A, ** represents a bonding position to B, and Z represents * -CONHSO 2 -**, * -SO 2 NHCO-**, * -N (R 2 ) CONHSO 2 -**, * -SO 2 NHCON (R 2 )-**, * -CONHSO 2 N (R 2 )-**, * -N (R 2 ) SO 2 NHCO-**, * -COCONHSO 2 -**, * -SO 2 NHCOCO-**, * -N (R 2 ) COCONHSO 2- **, or * -SO 2 NHCOCON (R 2 )-** (wherein R 2 represents a hydrogen atom or lower alkyl, * represents a bonding position with B, ** represents a bond with C Indicates the binding position). }
Or a pharmaceutically acceptable salt thereof.
X may be substituted * — (CH 2 ) 3 — **, may be substituted * — (CH 2 ) m —O— (CH 2 ) n — **, may be substituted *-(CH 2 ) m —S (O) p — (CH 2 ) n — **, optionally substituted * — (CH 2 ) m —N (R 1 ) — (CH 2 ) n — **, optionally substituted * — (CH 2 ) m —CO— (CH 2 ) n — **, optionally substituted * — (CH 2 ) q —CO—N (R 1 ) — (CH 2 ) r — **, optionally substituted * — (CH 2 ) q —N (R 1 ) —CO— (CH 2 ) r — **, optionally substituted * — (CH 2 ) q —SO 2 —N (R 1 ) — (CH 2 ) r — **, optionally substituted * — (CH 2 ) q —N (R 1 ) —SO 2 — (CH 2 ) R -**, or * -C (R 1 ) = NO-** (wherein m, n, q and r are each independently 0 or an integer from 1 to 4; p Is 0, 1 or 2, R 1 is a hydrogen atom or lower alkyl, * represents the bonding position with A, and ** represents the bonding position with B, where m + n is 2. The compound according to claim 1 or a pharmaceutically acceptable salt thereof, wherein q is an integer of 2 or more, and q + r is an integer of 1 or more.
X is —O—, —S (O) p —, —N (R 1 ) —, —CH (R 1 ) —, —CO—, — (CH 2 ) 2 —, —CH═CH—, — CO—N (R 1 ) —, —N (R 1 ) —CO—, —SO 2 —N (R 1 ) —, or —N (R 1 ) —SO 2 — (wherein R 1 is hydrogen The compound or a pharmaceutically acceptable salt thereof according to claim 1, which is an atom or lower alkyl, and p is 0, 1 or 2.
X is optionally substituted * — (CH 2 ) m —O— (CH 2 ) n — **, optionally substituted * — (CH 2 ) m —S (O) p — (CH 2 ) n -**, or * -C (R 1 ) = NO-** (wherein, m and n are each independently 0 or an integer from 1 to 4, and p is 0 1 or 2, R 1 is a hydrogen atom or lower alkyl, * represents a bonding position with A, ** represents a bonding position with B, provided that m + n is 2 or more Or a pharmaceutically acceptable salt thereof.
B is an optionally substituted biarylene or an optionally substituted divalent aromatic heterocyclic group;
X may be substituted * — (CH 2 ) m —O— (CH 2 ) n — **, or may be substituted * — (CH 2 ) m —S (O) p — ( CH 2 ) n -** (wherein, m and n are each independently 0 or an integer of 1 to 4, p is 0, 1 or 2, and * is the position of bonding with A) And ** represents a bonding position with B.) or a pharmaceutically acceptable salt thereof.
B is an optionally substituted phenylene,
X is * — (CH 2 ) m —O— (CH 2 ) n — **, * — (CH 2 ) m —S— (CH 2 ) n — **, or * —CH═N—O—. ** (wherein, m and n are each independently an integer of 1 to 4, * represents a bonding position with A, and ** represents a bonding position with B). Item 1. The compound according to Item 1 or a pharmaceutically acceptable salt thereof.
Z is * -CONHSO 2 -**, * -SO 2 NHCO-**, * -NHCONHSO 2 -**, * -CONHSO 2 NH-**, * -CONCONHSO 2 -**, or * -NHCONCONHSO 2 The compound according to any one of claims 1 to 6 or a compound thereof, wherein-** (wherein * represents a bonding position with B and ** represents a bonding position with C). Pharmaceutically acceptable salt.
The compound or a pharmaceutically acceptable salt thereof according to any one of claims 1 and 5 to 7, wherein X is -CH 2 -O-CH 2 -or -CH 2 -S-CH 2- .
The compound or a pharmaceutically acceptable salt thereof according to any one of claims 1 to 8, wherein C is aryl which may be substituted.
The compound according to any one of claims 1 to 8, or a pharmaceutically acceptable salt thereof, wherein C is an optionally substituted alkyl or an optionally substituted cycloalkylalkyl.
The compound represented by the general formula (I) is:
(1) N- [4- (biphenyl-4-ylmethylsulfanylmethyl) benzoyl] octane-1-sulfonamide,
(2) N- [4- (biphenyl-4-ylmethoxymethyl) benzoyl] -2,4-dichlorobenzenesulfonamide,
(3) N- [4- (biphenyl-4-ylmethoxymethyl) benzoyl] octane-1-sulfonamide,
(4) N- [4- (biphenyl-4-ylmethylsulfanylmethyl) benzoyl] hexane-1-sulfonamide,
(5) N- [4- (biphenyl-4-ylmethylsulfanylmethyl) benzoyl] -4-cyclopropylbutane-1-sulfonamide,
(6) N- [4- (biphenyl-4-ylmethoxymethyl) benzoyl] heptane-1-sulfonamide, or (7) N- [4- (biphenyl-4-ylmethoxymethyl) benzoyl] -5-cyclo The compound according to claim 1, which is propylpentane-1-sulfonamide, or a pharmaceutically acceptable salt thereof.
The compound represented by the general formula (I) is:
(1) 4- (4-Isopropylbenzyloxymethyl) -N- (heptylaminosulfonyl) benzamide,
(2) N- {2- [4- (4-isopropylbenzyloxymethyl) phenyl] -2-oxoacetyl} octane-1-sulfonamide,
(3) N- [4- (4-isopropylbenzyloxymethyl) phenyl] -2- (octane-1-sulfamoylamino) -2-oxoacetamide,
(4) N- [4- (biphenyl-4-ylmethylsulfanylmethyl) phenyl] -2- (hexane-1-sulfonylamino) -2-oxoacetamide, or (5) N- {2- [4- (biphenyl) The compound or a pharmaceutically acceptable salt thereof according to claim 1, which is -4-ylmethylsulfanylmethyl) phenyl] -2-oxoacetyl} hexane-1-sulfonamide.
The compound represented by the general formula (I) is:
(1) N- [4- (3′-methoxybiphenyl-4-ylmethylsulfanylmethyl) benzoyl] hexane-1-sulfonamide,
(2) N- {4- [3 ′-(trifluoromethyl) biphenyl-4-ylmethylsulfanylmethyl] benzoyl} hexane-1-sulfonamide,
(3) N- {4- [4- (1,4-benzodioxan-6-yl) benzylsulfanylmethyl] benzoyl} hexane-1-sulfonamide,
(4) N- {4- [3 ′-(trifluoromethyl) biphenyl-4-ylmethoxymethyl] benzoyl} hexane-1-sulfonamide, or (5) N- [4- (3′-methoxybiphenyl- The compound according to claim 1, which is 3-ylmethylsulfanylmethyl) benzoyl] hexane-1-sulfonamide, or a pharmaceutically acceptable salt thereof.
The compound represented by the general formula (I) is:
(1) (E) -N-({4- [3 ′-(trifluoromethyl) biphenyl-4-yl] methyleneaminooxy} benzoyl) hexane-1-sulfonamide,
(2) (E) -N-({4- [4- (1,4-benzodioxan-6-yl) phenyl] methyleneaminooxy} benzoyl) hexane-1-sulfonamide,
(3) (E) -N- [4- (3′-dimethylaminobiphenyl-4-ylmethyleneaminooxy) benzoyl] hexane-1-sulfonamide, or (4) (E) -N- [4- ( The compound or a pharmaceutically acceptable salt thereof according to claim 1, which is 3'-methoxybiphenyl 4-ylmethyleneaminooxy) benzoyl] hexane-1-sulfonamide.
The compound represented by the general formula (I) is:
(1) N-{[4- (3′-methoxybiphenyl-4-ylmethylsulfanylmethyl) phenyl] -2-oxoacetyl} hexane-1-sulfonamide, or (2) N-({4- [4 The compound or a pharmaceutically acceptable salt thereof according to claim 1, which is-(1,4-benzodioxan-6-yl) benzylsulfanylmethyl] phenyl} -2-oxoacetyl) hexane-1-sulfonamide.
A pharmaceutical composition comprising the compound according to any one of claims 1 to 15 or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier.
A PTP-1B inhibitor comprising the compound according to any one of claims 1 to 15 or a pharmaceutically acceptable salt thereof as an active ingredient.
A medicament comprising the PTP-1B inhibitor according to claim 17 as an active ingredient.
The pharmaceutical composition according to claim 16, for the prevention or treatment of a disease involving PTP-1B.
The pharmaceutical composition according to claim 16, for the prevention or treatment of a disease selected from the group consisting of diabetes, hyperglycemia, diseases caused by insulin resistance, diabetic complications, and impaired glucose tolerance.
The pharmaceutical composition according to claim 16, for prevention or treatment of a disease selected from the group consisting of arteriosclerosis, hyperlipidemia, obesity, cancer, inflammatory disease and metabolic syndrome.