Oxo-substituted compound

Abstract

Provided is a novel compound that has an excellent β-lactamase inhibitory effect. More specifically, provided is a compound represented by formula (1a), (1b) or (11) having an excellent β-lactamase inhibitory effect or a pharmaceutically acceptable salt thereof. By using this compound either in combination with a β-lactam drug or alone, a useful preventive or therapeutic agent for bacterial infections is provided. Also provided are useful preventive or therapeutic agents for treating various diseases with the combined use of the aforesaid compound and β-lactam drugs.

Description

Oxo-substituted compounds

[0001] The present invention relates to an oxo-substituted compound or a pharmaceutically acceptable salt thereof that is useful as a pharmaceutical. More specifically, the present invention relates to a pharmaceutical composition containing a novel oxo-substituted compound or a pharmaceutically acceptable salt thereof. The present invention also relates to a therapeutic agent containing the oxo-substituted compound or a pharmaceutically acceptable salt thereof.

[0002] Since the discovery of penicillin, antibiotics have played an important role in the treatment of infectious diseases. Among these, β-lactam antibiotics (e.g., penicillins, cephalosporins, and carbapenems) are the most commonly used drugs for the treatment of bacterial infections due to their strong bactericidal activity and high safety profile. However, with the increased use of β-lactam antibiotics, the emergence and spread of pathogens resistant to these antibiotics has become a global problem. The mechanisms by which these pathogens acquire resistance include the production of β-lactamases, structural changes in the target molecules of β-lactam antibiotics, decreased drug permeability into the bacterial cell, and increased drug efflux. In particular, the production of β-lactamases, which degrade and inactivate β-lactam antibiotics, is one of the factors that most significantly impact the maintenance of β-lactam efficacy. Various bacteria have evolved β-lactamases that counteract the efficacy of various β-lactam antibiotics. Based on their amino acid sequences, β-lactamases can be classified into four classes, namely Ambler class A, B, C, and D. Class A, C, and D enzymes have a serine residue at the center of their enzymatic activity and are therefore called serine-β-lactamases, while class B enzymes do not have a serine residue at the center of their enzymatic activity and rely on the metal ion zinc (Zn ２＋ ), and therefore are called metallo-β-lactamases (zinc-β-lactamases).

[0003] It has already been confirmed that the combined use of a β-lactamase inhibitor and a β-lactam drug is effective in solving the problem of resistance due to the production of β-lactamase, and it is known that the commercially available β-lactamase inhibitors clavulanic acid, sulbactam, and tazobactam primarily inhibit class A β-lactamases excluding KPC (Klebsiella pneumoniae carbapenemase), while avibactam inhibits class A β-lactamases including KPC, class C β-lactamases, and some class D β-lactamases including OXA-48 (Non-Patent Document 1). However, these existing β-lactamase inhibitors cannot effectively and broadly inhibit all β-lactamases produced by various bacteria, and for example, they are ineffective against class B metallo-β-lactamases. Furthermore, in recent years, β-lactamases collectively known as ESBLs (Extended Spectrum β-lactamases) have been isolated that can degrade a greater number of substrates (β-lactam drugs) than conventional β-lactamases. These β-lactamases have become a problem in Europe and the United States as new resistant bacteria, particularly as a cause of hospital-acquired infections. In addition, the emergence and spread of metallo-β-lactamase-producing bacteria is becoming a growing problem in Japan. Given this current situation, addressing β-lactamase-producing bacteria, including ESBLs and metallo-β-lactamases, has become an extremely important issue in preventing hospital-acquired infections. Furthermore, pathogenic bacteria evolve rapidly, making it highly likely that new β-lactamase-resistant bacteria will emerge. Therefore, in order to provide solutions to these problems and prepare for these challenges, there is a need to develop new β-lactamase inhibitors that have a different structure from existing β-lactamase inhibitors and are therefore expected to have a broader spectrum of β-lactamase inhibitory activity and metallo-β-lactamase inhibitory activity.

[0004] Recently, boronic acid derivatives having β-lactamase inhibitory activity have been reported in Patent Documents 1 to 9, etc. These Patent Documents describe oxo-substituted compounds included in the present invention, i.e., compounds having a non-aryl heterocyclic (preferably a nitrogen-containing non-aryl heterocyclic) structure at a side chain at a specific position and an oxo-substituent (-C(=O)-, -S(=O)-, -S(=O) ２There is no disclosure of the structure of a group of boronic acid compounds having the following substituents:

[0005] WO2014 / 107535WO2014 / 107536WO2015 / 179308WO2016 / 003929WO2016 / 149393WO2014 / 089365WO2014 / 110442WO2014 / 151958WO2015 / 191907

[0006] Buynak. J.D. Expert Opinion on Therapeutic Patents, 2013, 23(11), 1469-1481.

[0007] The present invention provides novel compounds having excellent β-lactamase inhibitory activity, and provides a useful agent for preventing or treating bacterial infections, either in combination with a β-lactam drug or as a single agent. Specifically, the present invention provides a useful agent for preventing or treating diseases, such as sepsis, febrile neutropenia, bacterial meningitis, bacterial endocarditis, otitis media, sinusitis, pneumonia, lung abscess, empyema, secondary infections of chronic respiratory lesions, pharyngitis / laryngitis, tonsillitis, osteomyelitis, arthritis, peritonitis, intraperitoneal abscess, cholecystitis, cholangitis, liver abscess, deep skin infections, lymphangitis / lymphadenitis, secondary infections of trauma / burns, surgical wounds, and the like, urinary tract infections, genital infections, eye infections, and dental infections, in combination with a β-lactam drug.

[0008] More specifically, the present inventors have found that compounds represented by the following formula (1a), (1b) or (11), or pharmaceutically acceptable salts thereof (hereinafter sometimes referred to as "compounds of the present invention") have excellent β-lactamase inhibitory activity, and have completed the present invention. That is, the present invention is as follows:

[0009] [Item A1] Formula (1a) or (1b): [In formulas (1a) and (1b), G represents an oxygen atom, a sulfur atom, or —NR ａ１ -, X is a hydroxyl group, an optionally substituted C １－６ an alkoxy group, or —NR ａ２ R ｂ１ and R ａ１ , R ａ２ and R ｂ１are each independently the same or different and are each independently selected from the group consisting of: 1) a hydrogen atom, 2) C １－６ an alkyl group; 3) C ３－１０ Alicyclic group, 4)C ６－１０ aryl 5) 5- or 6-membered heteroaryl; 6) 4- to 10-membered non-aryl heterocycle; 7) C １－６ Alkylcarbonyl group, 8) C ３－１０ 9) an alicyclic carbonyl group, C ６－１０ 10) an arylcarbonyl group, 11) a 5- or 6-membered heteroarylcarbonyl group, １－６ an alkylsulfonyl group, 12) C ３－１０ alicyclic sulfonyl group, 13) C ６－１０ 14) an arylsulfonyl group, 15) a 5- or 6-membered heteroarylsulfonyl group, or 16) an -OR ｃ１ (However, each of the substituents in 2) to 14) above may be substituted), wherein R ａ２ and R ｂ１ may be joined together to form an optionally substituted 4- to 10-membered nitrogen-containing non-aryl heterocycle, R ｃ１ is 1) a hydrogen atom, 2) C １－６ an alkyl group; 3) C ３－１０ Alicyclic group, 4)C ６－１０ 5) aryl, 5) 5- or 6-membered heteroaryl, or 6) 4- to 10-membered non-aryl heterocycle (provided that each of the substituents in 2) to 6) above may be substituted), L １ represents a single bond, an oxygen atom, a sulfur atom, -SO-, -SO ２ -, -NR ｄ -, -NR ｄ C(=O)- or -NR ｄ SO ２ - and L ２ represents a single bond or an optionally substituted C １－６ an alkylene group, and Z is 1) a hydrogen atom, 2) a hydroxyl group, 3) a cyano group, 4) a carboxyl group, 5) C ３－１０ Alicyclic group, 6)C ６－１０ aryl, 7) 5- or 6-membered heteroaryl, 8) 4- to 10-membered non-aryl heterocycle, 9) C１－６ 10) an alkoxy group; ３－１０ 11) an alicyclic oxy group, ６－１０ 12) an aryloxy group, 13) a 4- to 10-membered non-aryl heterocyclic oxy group, 14) C １－６ Alkylthio group, 15) C ３－１０ alicyclic thio group, 16) C ６－１０ 17) an arylthio group, 18) a 4- to 10-membered non-aryl heterocyclic thio group (provided that each of the substituents in 5) to 18) above may be substituted). 19) —SO ２ -NR ｅ１ R ｆ１ , 20)-NR ｅ１ -C(=O)OR ｆ１ , 21)-NR ｇ１ -C(=O)NR ｅ１ R ｆ１ , 22)-NR ｅ１ -C(=S)R ｆ１ , 23)-NR ｅ１ -C(=S) OR ｆ１ , 24)-NR ｇ１ -C(=S)NR ｅ１ R ｆ１ , 25)-NR ｇ１ -CR ｅ１ (=NR ｆ１ ), 26)-NR ｇ１ -CR ｅ１ (=N-OR ｆ１ ), 27)-NR ｈ１ -C(=NR ｇ１ ) NR ｅ１ R ｆ１ , 28)-NR ｈ１ -C(=N-OR ｇ１ ) NR ｅ１ R ｆ１ , 29)-NR ｉ１ -C(=NR ｈ１ ) NR ｇ１ -NR ｅ１ R ｆ１ , 30)-NR ｉ１ -C(=N-OR ｈ１ ) NR ｇ１ -NR ｅ１ R ｆ１ , 31)-NRｅ１ -SO ２ -R ｆ１ , 32)-NR ｇ１ -SO ２ -NR ｅ１ R ｆ１ , 33)-C(=O)OR ｅ１ , 34)-C(=S)OR ｅ１ , 35)-C(=S)NR ｅ１ R ｆ１ , 36)-C(=S)NR ｅ１ OR ｆ１ , 37)-C(=S)NR ｇ１ -NR ｅ１ R ｆ１ , 38)-C(=NR ｅ１ ) R ｆ１ , 39)-C(=N-OR ｅ１ ) R ｆ１ , 40)-C(=NR ｈ１ ) NR ｇ１ -NR ｅ１ R ｆ１ , 41)-C(=N-OR ｈ１ ) NR ｇ１ -NR ｅ１ R ｆ１ , 42)-NR ｅ１ R ｆ１ , 43)-NR ｇ１ -NR ｅ１ R ｆ１ , 44)-NR ｅ１ OR ｆ１ , 45)-NR ｅ１ -C(=O)R ｆ１ , 46)-C(=O)NR ｅ１ R ｆ１ , 47)-C(=O)NR ｅ１ OR ｆ１ , 48)-C(=O)NR ｇ１ -NR ｅ１ R ｆ１ , 49)-C(=O)R ｅ１ , 50)-C(=NR ｇ１ ) NR ｅ１ R ｆ１ , or 51)-C(=N-OR ｈ１ ) NR ｅ１ R ｆ１ R １ , R ２and R ３ Any one of the following formula (2): [In formula (2), Y represents an oxygen atom, a sulfur atom, or —NR ｊ -, ring A is an optionally substituted 4- to 20-membered non-aryl heterocycle, L ３ is -C(=O)-, -S(=O)-, or -S(=O) ２ - and L ４ is 1) a single bond, 2) C １－６ an alkylene group; 3) C ３－１０ 4) a cycloalkylene group, ６－１０ arylene group 5) a 5- or 6-membered heteroarylene group, 6) a 4- to 10-membered non-aryl heterocyclylene group, or 7) —C(═N—OR ｈ１ )-(wherein each of the substituents 2) to 6) above may be substituted), R ５ is 1) a hydrogen atom, 2) C １－６ an alkyl group; 3) C ３－１０ alicyclic group, 4) 4- to 10-membered non-aryl heterocycle, 5) C ６－１０ aryl, 6) 5- or 6-membered heteroaryl, 7) C １－６ an alkylthio group, or (provided that each of the substituents in 2) to 7) above may be substituted); 8) —NR ｅ１ OH, or １ , R ２ and R ３ the remaining two are the same or different and independently represent a hydrogen atom, a halogen atom, an optionally substituted C １－６ alkyl group, optionally substituted C １－６ an alkoxy group, optionally substituted C １－６ an alkylthio group, an optionally substituted 5- or 6-membered heteroaryl, or —NR ａ３ R ｂ２ and R ｄ , R ｅ１ , R ｅ２ , R ｆ１ , R ｆ２ , R ｇ１ , R ｇ２ , Rｈ１ , R ｈ２ , R ｉ１ , R ｉ２ and R ｊ are each independently the same or different and represent a hydrogen atom, an optionally substituted C １－６ alkyl group, optionally substituted C ３－１０ Alicyclic group, optionally substituted C ６－１０ aryl, an optionally substituted 5- or 6-membered heteroaryl, or an optionally substituted 4- to 10-membered non-aryl heterocycle; R ｅ１ and R ｆ１ or R ｅ２ and R ｆ２ When the combination of R is bonded to the same nitrogen atom, they may be joined together to form an optionally substituted 4- to 10-membered nitrogen-containing non-aryl heterocycle, ４ 1) -C(=O)R ８ , 2)-SO ２ -L ６ -R ８ (above 1) and 2) in the formula, R ８ is -NR ａ５ R ｂ４ , -NR ａ５ -L ７ -B(OR ｍ１ ) ２ , -OR ｍ１ or optionally substituted C １－６ is an alkyl group, and L ６ represents a single bond or -NR ａ６ -), 3) -NR ａ４ R ｂ３ , 4)-B(OR ｍ１ ) ２ , 5)-PO(OR ｍ１ ) (OR ｍ２ 6) an optionally substituted 5-membered heteroaryl, 7) an optionally substituted 5-membered non-aryl heterocycle, or 8) a bioisostere of any of 1) to 7) (provided that the formulae 2), 4), 5) and 6) above include carboxylic acid equivalents, and 8) may include these in duplicate), R ａ３ , R ａ４ , R ａ５ , R ａ６, R ｂ２ , R ｂ３ and R ｂ４ are each independently the same or different and represent the R ａ１ , R ａ２ and R ｂ１ where R ａ３ and R ｂ２ , R ａ４ and R ｂ３ or R ａ５ and R ｂ４ When a combination of R is bonded to the same nitrogen atom, they may be joined together to form an optionally substituted 4- to 10-membered nitrogen-containing non-aryl heterocycle, ｍ１ is 1) a hydrogen atom, 2) C １－６ an alkyl group; 3) C ３－１０ Alicyclic group, 4)C ６－１０ 5) aryl, 5) 5- or 6-membered heteroaryl, or 6) 4- to 10-membered non-aryl heterocycle (provided that each of the substituents in 2) to 6) above may be substituted), provided that R ｍ１ is bonded to the boron atom via an oxygen atom, two R ｍ１ is C ２－４ The alkylene may be taken together with the boron atom and two oxygen atoms to form a 5- to 7-membered non-aryl heterocycle (the alkylene portion of the non-aryl heterocycle may be substituted), and R ｍ２ represents a hydrogen atom, an optionally substituted C １－６ an alkyl group or an optionally substituted C ３－１０ is an alicyclic group, ７ is an optionally substituted C １－３ [Item A2] L is an alkylene group. or a pharmaceutically acceptable salt thereof. １ represents a single bond, a sulfur atom, or -NR ｄ C(=O)- or -NR ｄ SO ２ - and L ２ represents a single bond or an optionally substituted C １－６ an alkylene group, Z being 1) a hydrogen atom, 2) a hydroxyl group, 3) C ３－１０ Alicyclic group, 4)C６－１０ aryl, 5) 5- or 6-membered heteroaryl, 6) 4- to 10-membered non-aryl heterocycle, 7) —C(═N—OR ｅ１ ) R ｆ１ , or 8) -NR ｅ１ R ｆ１ [Item A3] The compound according to Item A1, or a pharmaceutically acceptable salt thereof, wherein Z-L ２ -L １ is a hydrogen atom, optionally substituted C １－６ an alkyl group or an optionally substituted C １－６ The compound according to item A1 or A2, or a pharmaceutically acceptable salt thereof, wherein Z-L is an alkylthio group. [Item A4] ２ -L １ [Item A5] The compound or a pharmaceutically acceptable salt thereof according to any one of Items A1 to A4, wherein G is an oxygen atom. [Item A6] X is a hydroxyl group or an optionally substituted C １－６ [Item A7] The compound according to any one of Items A1 to A6, or a pharmaceutically acceptable salt thereof, wherein X is an alkoxy group. [Item A8] The compound according to any one of Items A1 to A6, or a pharmaceutically acceptable salt thereof, wherein X is a hydroxyl group. [Item A9] The compound according to any one of Items A1 to A6, or a pharmaceutically acceptable salt thereof, wherein X is a hydroxyl group. [Item A10] The compound according to any one of Items A1 to A2, or a pharmaceutically acceptable salt thereof, wherein X is a hydroxyl group. [Item A11] The compound according to any one of Items A1 to A3, or a pharmaceutically acceptable salt thereof, wherein X is a hydroxyl group. [Item A12] The compound according to any one of Items A1 to A2, or a pharmaceutically acceptable salt thereof, wherein X is a hydroxyl group. [Item A13] The compound according to any one of Items A1 to A2, or a pharmaceutically acceptable salt thereof, wherein X is a hydroxyl group. [Item A14] The compound according to any one of Items A1 to A2, or a pharmaceutically acceptable salt thereof, wherein X is a hydroxyl group. [Item A15] The compound according to any one of Items A1 to A2, or a pharmaceutically acceptable salt thereof, wherein X is a hydroxyl group. [Item A16] The compound according to any one of Items A1 to A2, or a pharmaceutically acceptable salt thereof, wherein X is a hydroxyl group. [Item A17] The compound according to any one of Items A1 to A2, or a pharmaceutically acceptable salt thereof, wherein X is a hydroxyl group. [Item A18] The compound according to any one of Items A1 to A2, or a pharmaceutically acceptable salt thereof, wherein X is a hydroxyl group. [Item A19] The compound according to any one of Items A1 [In formulas (3a) and (3b), X, R １ , R ２ and R ３ is as defined in any one of paragraphs A1 to A7, and R ４ is 1)-COOR ｍ１ (where R ｍ１ is a hydrogen atom, C １－６ Alkyl group, C ３－１０ Alicyclic group, C ６－１０ aryl, 5- or 6-membered heteroaryl, or 4- to 10-membered non-aryl heterocycle, wherein said C １－６ Alkyl group, ３－１０ alicyclic group, said C ６－１０1) a compound or a pharmaceutically acceptable salt thereof according to any one of items A1 to A7, wherein R is selected from the group consisting of: R, the 5- or 6-membered heteroaryl, and the 4- to 10-membered non-aryl heterocycle, each of which may be optionally substituted; and 2) a biological equivalent of 1). [Item A9] R ４ is 1) —COOH (i.e., a carboxyl group), or 2) a carboxylic acid equivalent. [Item A10] The compound according to item A8, or a pharmaceutically acceptable salt thereof, wherein the compounds of formulae (1a) and (1b) or the compounds of formulae (3a) and (3b) are the following formulae (4a) and (4b), respectively: [In formulas (4a) and (4b), X, R ４ , Y, Ring A, L ３ , L ４ , and R ５ is as defined in any one of paragraphs A1 to A9, and R １ and R ２ are each independently the same or different and represent a hydrogen atom, a halogen atom, or C １－６ Alkyl group, C １－６ Alkoxy group (provided that the C １－６ Alkyl group and C １－６The alkoxy group may be substituted with 1 to 5 halogen atoms).] The compound according to any one of Items A1 to A9, or a pharmaceutically acceptable salt thereof. [Item A11] The compound according to any one of Items A1 to A10, or a pharmaceutically acceptable salt thereof, wherein Ring A is an optionally substituted 4- to 10-membered non-aryl heterocycle. [Item A12] The compound according to any one of Items A1 to A11, or a pharmaceutically acceptable salt thereof, wherein Ring A is an optionally substituted 4- to 7-membered non-aryl heterocycle. [Item A13] The compound according to any one of Items A1 to A12, or a pharmaceutically acceptable salt thereof, wherein Y is an oxygen atom or a sulfur atom. [Item A14] The compound according to any one of Items A1 to A13, or a pharmaceutically acceptable salt thereof, wherein Y is an oxygen atom. [Item A15] The compounds of formulas (1a) and (1b), or the compounds of formulas (3a) and (3b), or the compounds of formulas (4a) and (4b) are represented by the following formulas (5a) and (5b), respectively: [In formulas (5a) and (5b), ring A is an optionally substituted 4- to 6-membered nitrogen-containing non-aryl heterocycle.] or a pharmaceutically acceptable salt thereof according to any one of items A1 to A14. [Item A16] L ３ is -C(=O)- or -S(=O) ２ [Item A17] The compound according to any one of Items A1 to A15, or a pharmaceutically acceptable salt thereof, wherein L ３ The compound according to any one of items A1 to A16, wherein is —C(═O)—, or a pharmaceutically acceptable salt thereof. [Item A18] L ４ is a single bond, -C(=N-OR ｈ１ )- or optionally substituted C １－６ an alkylene group, where R ｈ１ is optionally substituted C １－６ The compound according to any one of items A1 to A17, or a pharmaceutically acceptable salt thereof, wherein L is an alkyl group. [Item A19] ４ is a single bond or -NR ２１ R ２２ Or = NOR２３ C optionally substituted with １－６ an alkylene group, where R ２１ , R ２２ and R ２３ are each independently a hydrogen atom, an optionally substituted C １－６ The compound according to any one of Items A1 to A18, wherein L is an alkyl group or an optionally substituted 4- to 10-membered non-aryl heterocyclic carbonyl group, or a pharmaceutically acceptable salt thereof. [Item A20] L ４ is a single bond, -CH ２ -, -CH(NH ２ ) -, or -CH(NH ２ )-CH ２ -, where L ４ When an amino group is present in the ３ [Item A21] The compound according to any one of Items A1 to A19, or a pharmaceutically acceptable salt thereof, wherein R ５ represents a hydrogen atom, an optionally substituted C １－６ an alkyl group, an optionally substituted 4- to 10-membered non-aryl heterocycle, an optionally substituted C ６－１０ Aryl, optionally substituted 5- or 6-membered heteroaryl, optionally substituted C １－６ an alkylthio group, or —NR ｅ１ OH, where R ｅ１ represents a hydrogen atom or an optionally substituted C １－６ The compound according to any one of items A1 to A20, or a pharmaceutically acceptable salt thereof, wherein R is an alkyl group. [Item A22] ５ is an optionally substituted 5- or 6-membered heteroaryl or an optionally substituted C ６－１０ The compound according to any one of Items A1 to A21, or a pharmaceutically acceptable salt thereof, wherein L is aryl. [Item A23] L ４ is a single bond, and R ５ is -NR ｅ１ OH, where R ｅ１ represents a hydrogen atom or an optionally substituted C １－６The compound according to any one of items A1 to A21, or a pharmaceutically acceptable salt thereof, wherein R is an alkyl group. [Item A24] ５ is as follows: and the subscript d is selected from the group consisting of R ５ is the number of substitutable positions on the ring of each R ６ａ are independently: 1) a hydrogen atom, 2) a hydroxyl group, 3) a cyano group, 4) a halogen, 5) C １－４ 6) an alkyl group, ３－１０ Alicyclic group, 7)C １－４ an alkoxy group, 8) C ３－１０ 9) an alicyclic oxy group, C ６－１０ 10) an aryloxy group, 11) a 4- to 10-membered non-aryl heterocyclic oxy group, (provided that each of the substituents in 5) to 11) above may be substituted). 12) —SO ２ -NR ｅ２ R ｆ２ , 13)-NR ｇ２ -CR ｅ２ (=NR ｆ２ ), 14)-NR ｇ２ -CR ｅ２ (=N-OR ｆ２ ), 15)-NR ｈ２ -C(=NR ｇ２ ) NR ｅ２ R ｆ２ , 16)-NR ｈ２ -C(=N-OR ｇ２ ) NR ｅ２ R ｆ２ , 17)-NR ｉ２ -C(=NR ｈ２ ) NR ｇ２ -NR ｅ２ R ｆ２ , 18)-NR ｉ２ -C(=N-OR ｈ２ ) NR ｇ２ -NR ｅ２ R ｆ２ , 19)-C(=NR ｅ２ ) R ｆ２ , 20)-C(=N-OR ｅ２ ) R ｆ２ , 21)-C(=NR ｈ２ )-NR ｅ２ Rｆ２ , 22)-C(=NR ｈ２ ) NR ｇ２ -NR ｅ２ R ｆ２ , 23)-C(=N-OR ｈ２ ) NR ｇ２ -NR ｅ２ R ｆ２ , 24)-NR ｅ２ R ｆ２ , 25)-NR ｇ２ -NR ｅ２ R ｆ２ , 26)-NR ｅ２ OR ｆ２ , 27)-NR ｅ２ -C(=O)R ｆ２ , 28)-C(=O)NR ｅ２ R ｆ２ , 29)-C(=O)NR ｅ２ OR ｆ２ , 30)-C(=O)NR ｇ２ -NR ｅ２ R ｆ２ , 31)-C(=O)R ｅ２ , 32)-C(=O)OR ｅ２ , and 33)-C(=N-OR ｈ２ ) NR ｅ２ R ｆ２ and each R is selected from the group consisting of ６ｂ are independently: 1) a hydrogen atom; 2) a hydroxyl group; 3) C １－４ an alkyl group (wherein the alkyl group may be substituted); 4) C ３－１０ an alicyclic group, (however, the alicyclic group may be substituted); 5) —C(═NR ｅ２ ) R ｆ２ , 6)-C(=N-OR ｅ２ ) R ｆ２ , 7)-SO ２ -NR ｅ２ R ｆ２ , 8)-C(=NR ｈ２ )-NR ｅ２ R ｆ２ , 9)-C(=NR ｈ２ ) NR ｇ２ -NR ｅ２ R ｆ２ , 10)-C(=N-OR ｈ２ ) NR ｇ２ -NRｅ２ R ｆ２ , 11)-C(=O)NR ｅ２ R ｆ２ , 12)-C(=O)NR ｅ２ OR ｆ２ , 13)-C(=O)NR ｇ２ -NR ｅ２ R ｆ２ , 14)-C(=O)R ｅ２ , and 15)-C(=N-OR ｈ２ ) NR ｅ２ R ｆ２ [Item A25] The compound according to any one of Items A1 to A22, or a pharmaceutically acceptable salt thereof, selected from the group consisting of: １ and R ２ are each independently the same or different and are each independently selected from the group consisting of: 1) a hydrogen atom, 2) a halogen atom, 3) C １－６ 4) an alkyl group; １－６ an alkoxy group, and 5) C １－６ [Item A26] The compound according to any one of Items A1 to A24, wherein R is selected from the group consisting of alkylthio groups (wherein each of the substituents in 3) to 5) above may be substituted), or a pharmaceutically acceptable salt thereof. １ and R ２ are each independently the same or different and are each independently selected from the group consisting of: 1) a hydrogen atom, 2) a halogen atom, 3) an optionally substituted C １－６ [Item A27] The compound according to any one of items A1 to A25, or a pharmaceutically acceptable salt thereof, wherein R is selected from the group consisting of an alkyl group, １ and R ２ and (3a) and (3b) are each a hydrogen atom. [Item A28] The compound according to any one of items A1 to A26, or a pharmaceutically acceptable salt thereof, wherein the compounds of formulae (1a) and (1b), the compounds of formulae (3a) and (3b), the compounds of formulae (4a) and (4b), or the compounds of formulae (5a) and (5b) are each a hydrogen atom. [Item A29] The compound according to any one of items A1 to A26, or a pharmaceutically acceptable salt thereof, wherein [In formulas (6a) and (6b), L ３ , L ４ , and R ５is as defined in any one of items A1 to A24, m is an integer of 1, 2, or 3, n is an integer of 1, 2, or 3, and m+n is 2, 3, or 4.] The compound according to any one of items A1 to A27, or a pharmaceutically acceptable salt thereof. [Item A29] The compound according to any one of items A1 to A28, or a pharmaceutically acceptable salt thereof, wherein m is 1 or 2, n is 1 or 2, and m+n is 2 or 3. [Item A30] The compound according to any one of items A1 to A29, or a pharmaceutically acceptable salt thereof, wherein m is 1 and n is 1. [Item A31] R ５ is as follows: and the subscript d is a 5- or 6-membered aryl or heteroaryl selected from the group consisting of R ５ is the number of substitutable positions on the ring of each R ６ａ are independently: 1) a hydrogen atom, 2) a hydroxyl group, 3) a halogen, 4) C １－４ an alkyl group, wherein the alkyl group is NR ｅ２ R ｆ２ , -C(=O)OR ｆ２ or may be substituted with a hydroxyl group) 5) C １－４ Alkoxy group 6) -NR ｅ２ R ｆ２ , and 7) —C(═O)OR ｅ２ and each R is selected from the group consisting of ６ｂ are independently: 1) a hydrogen atom, 2) a hydroxyl group, and 3) C １－４ an alkyl group, wherein the alkyl group is NR ｅ２ R ｆ２ , -C(=O)OR ｆ２ or a hydroxyl group), or a pharmaceutically acceptable salt thereof. [Item A32] R ｅ２ and R ｆ２ are each independently the same or different and represent a hydrogen atom, an optionally substituted C １－６ an alkyl group or an optionally substituted C ３－１０The compound according to any one of Items A1 to A31, or a pharmaceutically acceptable salt thereof, wherein R is an alicyclic group. [Item A33] ｅ２ and R ｆ２ are each independently the same or different and represent a hydrogen atom or an optionally substituted C １－６ The compound according to any one of Items A1 to A32, or a pharmaceutically acceptable salt thereof, wherein R is an alkyl group. [Item A34] ｅ２ and R ｆ２ The compound according to any one of items A1 to A33, or a pharmaceutically acceptable salt thereof, wherein R is a hydrogen atom. [Item A35] ６ａ is -NR ｅ２ R ｆ２ and R ｅ２ and R ｆ２ is a hydrogen atom on one side and a C atom on the other side. １－４ The compound according to any one of Items A24 to A33, wherein the alkyl group is an alkyl group (which may be substituted with an amino group or a hydroxyl group), or a pharmaceutically acceptable salt thereof. [Item A36] The compound according to Item A1, or a pharmaceutically acceptable salt thereof, which is represented by the following compound name or structural formula: 7-[(1-acetylazetidin-3-yl)oxy]-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 8-[(1-acetylazetidin-3-yl)oxy]-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-({1-[(1H-imidazol-5-yl)acetyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 4,4-dihydroxy-8-({1-[(1H-imidazol-5-yl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidiabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-{[1-(methanesulfonyl)azetidin-3-yl]oxy}-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 4,4-dihydroxy-8-{[1-(methanesulfonyl)azetidin-3-yl]oxy}-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 7-({1-[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 8-({1-[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 7-({1-[(2-amino-1,3-thiazol-4-yl)(methoxyimino)acetyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 8-({1-[(2-amino-1,3-thiazol-4-yl)(methoxyimino)acetyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-{[1-(pyridine-2-carbonyl)azetidin-3-yl]oxy}-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 4,4-dihydroxy-8-{[1-(pyridine-2-carbonyl)azetidin-3-yl]oxy}-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-({1-[(methylsulfanyl)acetyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 4,4-dihydroxy-8-({1-[(methylsulfanyl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-{[1-(1H-1,2,4-triazole-3-carbonyl)azetidin-3-yl]oxy}-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 4,4-dihydroxy-8-{[1-(1H-1,2,4-triazole-3-carbonyl)azetidin-3-yl]oxy}-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-{[1-(1-oxido-2-pyridinylcarbonyl)azetidin-3-yl]oxy}-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 4,4-dihydroxy-8-{[1-(1-oxido-2-pyridinylcarbonyl)azetidin-3-yl]oxy}-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 7-({1-[(2R)-2-amino-2-phenylacetyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 8-({1-[(2R)-2-amino-2-phenylacetyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 7-[(1-benzoylazetidin-3-yl)oxy]-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid , 8-[(1-benzoylazetidin-3-yl)oxy]-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-{[1-(pyridine-3-carbonyl)azetidin-3-yl]oxy}-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 4,4-dihydroxy-8-{[1-(pyridine-3-carbonyl)azetidin-3-yl]oxy}-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-({1-[(pyridin-2-yl)acetyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 4,4-dihydroxy-8-({1-[(pyridin-2-yl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-({1-[(pyridin-3-yl)acetyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 4,4-dihydroxy-8-({1-[(pyridin-3-yl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 7-({1-[(2S)-2-amino-2-phenylacetyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 8-({1-[(2S)-2-amino-2-phenylacetyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-({1-[(pyridin-4-yl)acetyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 4,4-dihydroxy-8-({1-[(pyridin-4-yl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-({1-[(4-hydroxyphenyl)acetyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 4,4-dihydroxy-8-({1-[(4-hydroxyphenyl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-({1-[(1H-1,2,4-triazol-1-yl)acetyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 4,4-dihydroxy-8-({1-[(1H-1,2,4-triazol-1-yl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 7-({1-[amino(1H-imidazol-5-yl)acetyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 8-({1-[amino(1H-imidazol-5-yl)acetyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidiabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-{[1-(phenylacetyl)azetidin-3-yl]oxy}-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 4,4-dihydroxy-8-{[1-(phenylacetyl)azetidin-3-yl]oxy}-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-{[1-(3-phenylpropanoyl)azetidin-3-yl]oxy}-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 4,4-dihydroxy-8-{[1-(3-phenylpropanoyl)azetidin-3-yl]oxy}-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-({1-[(1H-imidazol-1-yl)acetyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 4,4-dihydroxy-8-({1-[(1H-imidazol-1-yl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidiabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-({1-[(1H-tetrazol-1-yl)acetyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 4,4-dihydroxy-8-({1-[(1H-tetrazol-1-yl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-({1-[(2H-tetrazol-5-yl)acetyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 4,4-dihydroxy-8-({1-[(2H-tetrazol-5-yl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-[(1-D-phenylalanylazetidin-3-yl)oxy]-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid , 4,4-dihydroxy-8-[(1-D-phenylalanylazetidin-3-yl)oxy]-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-[(1-D-tyrosylazetidin-3-yl)oxy]-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid , 4,4-dihydroxy-8-[(1-D-tyrosylazetidin-3-yl)oxy]-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 7-[(1-D-histidylazetidin-3-yl)oxy]-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid , 8-[(1-D-histidylazetidin-3-yl)oxy]-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-[(1-D-valylazetidin-3-yl)oxy]-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid , 4,4-dihydroxy-8-[(1-D-valylazetidin-3-yl)oxy]-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 7-[(1-L-histidylazetidin-3-yl)oxy]-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid , 8-[(1-L-histidylazetidin-3-yl)oxy]-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 7-[(1-{(2R)-2-[(4-ethyl-2,3-dioxopiperazine-1-carbonyl)amino]-2-phenylacetyl}azetidin-3-yl)oxy]-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 8-[(1-{(2R)-2-[(4-ethyl-2,3-dioxopiperazine-1-carbonyl)amino]-2-phenylacetyl}azetidin-3-yl)oxy]-4,4-dihydroxy-5-oxa-4-boranuidiabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-[(1-D-prolylazetidin-3-yl)oxy]-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid , 4,4-dihydroxy-8-[(1-D-prolylazetidin-3-yl)oxy]-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-[(1-L-prolylazetidin-3-yl)oxy]-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid , 4,4-dihydroxy-8-[(1-L-prolylazetidin-3-yl)oxy]-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 7-[(1-{[4-(2-aminoethyl)-1H-imidazol-1-yl]acetyl}azetidin-3-yl)oxy]-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 8-[(1-{[4-(2-aminoethyl)-1H-imidazol-1-yl]acetyl}azetidin-3-yl)oxy]-4,4-dihydroxy-5-oxa-4-boranuidiabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 7-{[1-(3,4-dihydroxybenzoyl)azetidin-3-yl]oxy}-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 8-{[1-(3,4-dihydroxybenzoyl)azetidin-3-yl]oxy}-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-{[1-(hydroxycarbamoyl)azetidin-3-yl]oxy}-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , and 4,4-dihydroxy-8-{[1-(hydroxycarbamoyl)azetidin-3-yl]oxy}-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid [Item A37] A salt of the compound according to Item A36, represented by the following compound name or structural formula: 8-({1-[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid disodium salt , 4,4-dihydroxy-8-({1-[(methylsulfanyl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid disodium salt , 4,4-dihydroxy-8-{[1-(1H-1,2,4-triazole-3-carbonyl)azetidin-3-yl]oxy}-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid disodium salt , 4,4-dihydroxy-8-{[1-(1-oxido-2-pyridinylcarbonyl)azetidin-3-yl]oxy}-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid disodium salt , 8-({1-[(2R)-2-amino-2-phenylacetyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid disodium salt , 8-[(1-benzoylazetidin-3-yl)oxy]-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid disodium salt , 4,4-dihydroxy-8-{[1-(pyridine-3-carbonyl)azetidin-3-yl]oxy}-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid disodium salt , 4,4-dihydroxy-8-({1-[(pyridin-2-yl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid disodium salt , 4,4-dihydroxy-8-({1-[(pyridin-3-yl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid disodium salt , 8-({1-[(2S)-2-amino-2-phenylacetyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid disodium salt , 4,4-dihydroxy-8-({1-[(pyridin-4-yl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid disodium salt , 4,4-dihydroxy-8-({1-[(4-hydroxyphenyl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid disodium salt , 4,4-dihydroxy-8-({1-[(1H-1,2,4-triazol-1-yl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid disodium salt , 8-({1-[amino(1H-imidazol-5-yl)acetyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidiabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid disodium salt , 4,4-dihydroxy-8-{[1-(phenylacetyl)azetidin-3-yl]oxy}-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid disodium salt , 4,4-dihydroxy-8-{[1-(3-phenylpropanoyl)azetidin-3-yl]oxy}-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid disodium salt , 4,4-dihydroxy-8-({1-[(1H-imidazol-1-yl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidiabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid disodium salt , 4,4-dihydroxy-8-({1-[(1H-tetrazol-1-yl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid disodium salt , 4,4-dihydroxy-8-({1-[(2H-tetrazol-5-yl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid disodium salt , 4,4-dihydroxy-8-[(1-D-phenylalanylazetidin-3-yl)oxy]-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid disodium salt , 4,4-dihydroxy-8-[(1-D-tyrosylazetidin-3-yl)oxy]-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid disodium salt , 8-[(1-D-histidylazetidin-3-yl)oxy]-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid disodium salt , 4,4-dihydroxy-8-[(1-D-valylazetidin-3-yl)oxy]-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid disodium salt , 8-[(1-L-histidylazetidin-3-yl)oxy]-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid disodium salt , 8-[(1-{(2R)-2-[(4-ethyl-2,3-dioxopiperazine-1-carbonyl)amino]-2-phenylacetyl}azetidin-3-yl)oxy]-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid disodium salt , 4,4-dihydroxy-8-[(1-D-prolylazetidin-3-yl)oxy]-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid disodium salt , 4,4-dihydroxy-8-[(1-L-prolylazetidin-3-yl)oxy]-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic acid disodium salt , and 8-[(1-{[4-(2-aminoethyl)-1H-imidazol-1-yl]acetyl}azetidin-3-yl)oxy]-4,4-dihydroxy-5-oxa-4-boranuidiabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid disodium salt [Item A38] The following formula (11): [In formula (11), R Ｇ is a hydroxyl group, a thiol group, or -NHR ａ１ and R ａ１ , Z, L １ , L ２ , X, R １ , R ２ , R ３ , and R ４has the same definition as in item A1, and formula (1a) has the same definition as in item A1], or a pharmaceutically acceptable salt thereof. [Item A39] A compound represented by formula (11) or a pharmaceutically acceptable salt thereof, [In formula (12), X, R １ , R ２ , R ３ , and R ４ has the same meaning as defined in Item A8]. [Item A40] The compound according to Item A38, or a pharmaceutically acceptable salt thereof, wherein the compound of formula (12) is a compound of the following formula (13): [In formula (13), X, Y, ring A, L ３ , L ４ , R １ , R ２ , R ４ , and R ５ [Item A41] The compound according to Item A38 or A39, wherein X and R are as defined in any one of Items A10 to A14 or A16 to A27, or a pharmaceutically acceptable salt thereof. Ｇ is a hydroxyl group, and R ４ is a carboxyl group, and ring A is an optionally substituted 4- to 6-membered nitrogen-containing non-aryl heterocycle, or a pharmaceutically acceptable salt thereof. [Item A42] The compound of formula (13) or a pharmaceutically acceptable salt thereof, [In formula (14), X, L ３ , L ４ , m, n, and R ５ [Item A43] The compound according to any one of Items A38 to A41, wherein R is as defined in Item A28, or a pharmaceutically acceptable salt thereof. Ｇ is a hydroxyl group or a thiol group, or a pharmaceutically acceptable salt thereof. [Item A44] R Ｇ [Item A45] The compound according to any one of Items A38 to A43, or a pharmaceutically acceptable salt thereof, wherein X is a hydroxyl group or C １－６[Item A46] The compound according to any one of Items A38 to A44, or a pharmaceutically acceptable salt thereof, wherein X is an alkoxy group. [Item A46] The compound according to any one of Items A38 to A45, or a pharmaceutically acceptable salt thereof, wherein X is a hydroxyl group. [Item A47] The compound according to any one of Items A42 to A46, or a pharmaceutically acceptable salt thereof, wherein m is 1 or 2, n is 1 or 2, and m+n is 2 or 3. [Item A48] The compound according to any one of Items A42 to A47, or a pharmaceutically acceptable salt thereof, wherein m is 1 and n is 1. [Item A49] L ３ The compound or a pharmaceutically acceptable salt thereof according to any one of Items A38 to A48, wherein L is as defined in Item A16 or A17. [Item A50] L ４ is as defined in any one of Items A18 to A20, or a pharmaceutically acceptable salt thereof. [Item A51] The compound according to Item A38 or a pharmaceutically acceptable salt thereof, selected from the group consisting of the following compounds: 6-[(1-acetylazetidin-3-yl)oxy]-3-(2-boronoethyl)-2-hydroxybenzoic acid , 3-(2-boronoethyl)-2-hydroxy-6-({1-[(1H-imidazol-5-yl)acetyl]azetidin-3-yl}oxy)benzoic acid , 3-(2-boronoethyl)-2-hydroxy-6-{[1-(methanesulfonyl)azetidin-3-yl]oxy}benzoic acid , 6-({1-[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]azetidin-3-yl}oxy)-3-(2-boronoethyl)-2-hydroxybenzoic acid , 6-({1-[(2-amino-1,3-thiazol-4-yl)(methoxyimino)acetyl]azetidin-3-yl}oxy)-3-(2-boronoethyl)-2-hydroxybenzoic acid , 3-(2-boronoethyl)-2-hydroxy-6-{[1-(pyridine-2-carbonyl)azetidin-3-yl]oxy}benzoic acid , 3-(2-boronoethyl)-2-hydroxy-6-({1-[(methylsulfanyl)acetyl]azetidin-3-yl}oxy)benzoic acid , 3-(2-boronoethyl)-2-hydroxy-6-{[1-(1H-1,2,4-triazole-3-carbonyl)azetidin-3-yl]oxy}benzoic acid , 3-(2-boronoethyl)-2-hydroxy-6-{[1-(1-oxido-2-pyridinylcarbonyl)azetidin-3-yl]oxy}benzoic acid , 6-({1-[(2R)-2-amino-2-phenylacetyl]azetidin-3-yl}oxy)-3-(2-boronoethyl)-2-hydroxybenzoic acid , 6-[(1-benzoylazetidin-3-yl)oxy]-3-(2-boronoethyl)-2-hydroxybenzoic acid , 3-(2-boronoethyl)-2-hydroxy-6-{[1-(pyridine-3-carbonyl)azetidin-3-yl]oxy}benzoic acid , 3-(2-boronoethyl)-2-hydroxy-6-({1-[(pyridin-2-yl)acetyl]azetidin-3-yl}oxy)benzoic acid , 3-(2-boronoethyl)-2-hydroxy-6-({1-[(pyridin-3-yl)acetyl]azetidin-3-yl}oxy)benzoic acid , 6-({1-[(2S)-2-amino-2-phenylacetyl]azetidin-3-yl}oxy)-3-(2-boronoethyl)-2-hydroxybenzoic acid , 3-(2-boronoethyl)-2-hydroxy-6-({1-[(pyridin-4-yl)acetyl]azetidin-3-yl}oxy)benzoic acid , 3-(2-boronoethyl)-2-hydroxy-6-({1-[(4-hydroxyphenyl)acetyl]azetidin-3-yl}oxy)benzoic acid , 3-(2-boronoethyl)-2-hydroxy-6-({1-[(1H-1,2,4-triazol-1-yl)acetyl]azetidin-3-yl}oxy)benzoic acid , 6-({1-[amino(1H-imidazol-5-yl)acetyl]azetidin-3-yl}oxy)-3-(2-boronoethyl)-2-hydroxybenzoic acid , 3-(2-boronoethyl)-2-hydroxy-6-{[1-(phenylacetyl)azetidin-3-yl]oxy}benzoic acid , 3-(2-boronoethyl)-2-hydroxy-6-{[1-(3-phenylpropanoyl)azetidin-3-yl]oxy}benzoic acid , 3-(2-boronoethyl)-2-hydroxy-6-({1-[(1H-imidazol-1-yl)acetyl]azetidin-3-yl}oxy)benzoic acid , 3-(2-boronoethyl)-2-hydroxy-6-({1-[(1H-tetrazol-1-yl)acetyl]azetidin-3-yl}oxy)benzoic acid , 3-(2-boronoethyl)-2-hydroxy-6-({1-[(2H-tetrazol-5-yl)acetyl]azetidin-3-yl}oxy)benzoic acid , 3-(2-boronoethyl)-2-hydroxy-6-[(1-D-phenylalanylazetidin-3-yl)oxy]benzoic acid , 3-(2-boronoethyl)-2-hydroxy-6-[(1-D-tyrosylazetidin-3-yl)oxy]benzoic acid , 3-(2-boronoethyl)-6-[(1-D-histidylazetidin-3-yl)oxy]-2-hydroxybenzoic acid , 3-(2-boronoethyl)-2-hydroxy-6-[(1-D-valylazetidin-3-yl)oxy]benzoic acid , 3-(2-boronoethyl)-6-[(1-L-histidylazetidin-3-yl)oxy]-2-hydroxybenzoic acid , 3-(2-boronoethyl)-6-[(1-{(2R)-2-[(4-ethyl-2,3-dioxopiperazine-1-carbonyl)amino]-2-phenylacetyl}azetidin-3-yl)oxy]-2-hydroxybenzoic acid , 3-(2-boronoethyl)-2-hydroxy-6-[(1-D-prolylazetidin-3-yl)oxy]benzoic acid , 3-(2-boronoethyl)-2-hydroxy-6-[(1-L-prolylazetidin-3-yl)oxy]benzoic acid , 6-[(1-{[4-(2-aminoethyl)-1H-imidazol-1-yl]acetyl}azetidin-3-yl)oxy]-3-(2-boronoethyl)-2-hydroxybenzoic acid , 3-(2-boronoethyl)-6-{[1-(3,4-dihydroxybenzoyl)azetidin-3-yl]oxy}-2-hydroxybenzoic acid , and 3-(2-boronoethyl)-2-hydroxy-6-{[1-(hydroxycarbamoyl)azetidin-3-yl]oxy}benzoic acid [Item A52] A pharmaceutical comprising the compound according to any one of Items A1 to A51 or a pharmaceutically acceptable salt thereof. [Item A53] The pharmaceutical according to Item A52, which is a therapeutic or prophylactic agent for bacterial infections. [Item A54] A β-lactamase inhibitor comprising, as an active ingredient, the compound according to any one of Items A1 to A51 or a pharmaceutically acceptable salt thereof. [Item A55] A pharmaceutical composition comprising the compound according to any one of Items A1 to A51 or a pharmaceutically acceptable salt thereof and a pharmaceutically acceptable carrier. [Item A56] The pharmaceutical composition according to Item A55, further comprising an additional drug. [Item A57] The pharmaceutical composition according to Item A56, wherein the additional drug is selected from the group consisting of antibacterial agents, antifungal agents, antiviral agents, anti-inflammatory agents and antiallergic agents. [Item A58] The pharmaceutical composition according to Item A56 or A57, wherein the additional drug is a β-lactam drug.[Item A59] The additional β-lactam drug is amoxicillin, ampicillin (pivampicillin, hetacillin, bacampicillin, metampicillin, talampicillin), epicillin, carbenicillin (carindacillin), ticarcillin, temocillin, azlocillin, piperacillin, mezlocillin, mecillinam (pivmecillinam), sulbenicillin, benzylpenicillin (G), clometocillin, benzathine benzylpenicillin, procaine benzylpenicillin, azidocillin, penamecillin, phenoxymethylpenicillin (V), ... Picillin, benzathine phenoxymethylpenicillin, phenethicillin, cloxacillin (dicloxacillin, flucloxacillin), oxacillin, methicillin, nafcillin, faropenem, biapenem, doripenem, ertapenem, imipenem, meropenem, panipenem, tomopenem, razupenem, cefazolin, cephacetrile, cefadroxil, cephalexin, cephaloglycin, cephalonium, cephaloridine, cephalothin, cephapirin, cefatrizine, cefazedone, cefazaflur, cephradine, cefradine Sajin, ceftezole, cefaclor, cefamandole, cefminox, cefonicid, ceforanide, cefotiam, cefprozil, cefbuperazone, cefuroxime, cefuzonam, cefoxitin, cefotetan, cefmetazole, loracarbef, cefixime, ceftazidime, ceftriaxone, cefcapene, cefdaloxime, cefdinir, cefditoren, cefetamet, cefmenoxime, cefodizime, cefoperazone, cefotaxime, cefpimizole, cefpiramide, cefpodoxime, cefsulodin, cefteram, The pharmaceutical composition according to Item A57 or A58, wherein the compound is selected from the group consisting of ceftibuten, ceftiolene, ceftizoxime, flomoxef, latamoxef, cefepime, cefozopran, cefpirome, cefquinome, ceftobiprole, ceftaroline, CXA-101, RWJ-54428, MC-04546, ME1036, BAL30072, SYN2416, ceftiofur, cefquinome, cefovecin, aztreonam, tigenonam, carumonam, RWJ-442831, RWJ-333441, and RWJ-333442.[Item A60] The pharmaceutical composition according to Item A58 or A59, wherein the β-lactam drug is selected from ceftazidime, biapenem, doripenem, ertapenem, imipenem, meropenem, or panipenem. [Item A61] The pharmaceutical composition according to Item A58 or A59, wherein the β-lactam drug is selected from aztreonam, tigenonam, BAL30072, SYN2416, or carumonam. [Item A62] The pharmaceutical composition according to Item A55, wherein the additional drug is administered together with an additional drug. [Item A63] The pharmaceutical composition according to Item A62, wherein the additional drug is selected from an antibacterial agent, an antifungal agent, an antiviral agent, an anti-inflammatory agent, or an antiallergic agent. [Item A64] The pharmaceutical composition according to Item A62 or A63, wherein the additional drug is a β-lactam drug.[Item A65] The additional β-lactam drug is amoxicillin, ampicillin (pivampicillin, hetacillin, bacampicillin, metampicillin, talampicillin), epicillin, carbenicillin (carindacillin), ticarcillin, temocillin, azlocillin, piperacillin, mezlocillin, mecillinam (pivmecillinam), sulbenicillin, benzylpenicillin (G), clometocillin, benzathine benzylpenicillin, procaine benzylpenicillin, azidocillin, penamecillin, phenoxymethylpenicillin (V), ... Picillin, benzathine phenoxymethylpenicillin, phenethicillin, cloxacillin (dicloxacillin, flucloxacillin), oxacillin, methicillin, nafcillin, faropenem, biapenem, doripenem, ertapenem, imipenem, meropenem, panipenem, tomopenem, razupenem, cefazolin, cephacetrile, cefadroxil, cephalexin, cephaloglycin, cephalonium, cephaloridine, cephalothin, cephapirin, cefatrizine, cefazedone, cefazaflur, cephradine, cefradine Sajin, ceftezole, cefaclor, cefamandole, cefminox, cefonicid, ceforanide, cefotiam, cefprozil, cefbuperazone, cefuroxime, cefuzonam, cefoxitin, cefotetan, cefmetazole, loracarbef, cefixime, ceftazidime, ceftriaxone, cefcapene, cefdaloxime, cefdinir, cefditoren, cefetamet, cefmenoxime, cefodizime, cefoperazone, cefotaxime, cefpimizole, cefpiramide, cefpodoxime, cefsulodin, cefteram, The pharmaceutical composition according to Item A63 or A64, wherein the compound is selected from the group consisting of ceftibuten, ceftiolene, ceftizoxime, flomoxef, latamoxef, cefepime, cefozopran, cefpirome, cefquinome, ceftobiprole, ceftaroline, CXA-101, RWJ-54428, MC-04546, ME1036, BAL30072, SYN2416, ceftiofur, cefquinome, cefovecin, aztreonam, tigenonam, carumonam, RWJ-442831, RWJ-333441, and RWJ-333442.[Item A66] The pharmaceutical composition according to Item A64 or A65, wherein the β-lactam drug is selected from the group consisting of ceftazidime, biapenem, doripenem, ertapenem, imipenem, meropenem, and panipenem. [Item A67] The pharmaceutical composition according to Item A64 or A65, wherein the β-lactam drug is selected from the group consisting of aztreonam, tigenonam, BAL30072, SYN2416, and carumonam. [Item A68] The compound according to any one of Items A1 to A51, or a pharmaceutically acceptable salt thereof, for treating a bacterial infection. [Item A69] The compound according to Item A68, or a pharmaceutically acceptable salt thereof, wherein the bacterial infection is a bacterial infection involving a bacterium capable of possessing β-lactamase. [Item A70] The compound according to Item A68 or A69, wherein the bacterial infection is sepsis, febrile neutropenia, bacterial meningitis, bacterial endocarditis, otitis media, sinusitis, pneumonia, lung abscess, empyema, secondary infection of chronic respiratory lesion, pharyngitis / laryngitis, tonsillitis, osteomyelitis, arthritis, peritonitis, intraperitoneal abscess, cholecystitis, cholangitis, liver abscess, deep skin infection, lymphangitis / lymphadenitis, secondary infection of trauma / burn, surgical wound or the like, urinary tract infection, genital infection, eye infection or dental infection, or a pharmaceutically acceptable salt thereof. [Item A71] A pharmaceutical composition comprising a compound according to any one of Items A1 to A51 or a pharmaceutically acceptable salt thereof in combination with at least one drug selected from the group consisting of therapeutic agents for sepsis, febrile neutropenia, bacterial meningitis, bacterial endocarditis, otitis media, sinusitis, pneumonia, lung abscess, empyema, secondary infections of chronic respiratory lesions, pharyngitis / laryngitis, tonsillitis, osteomyelitis, arthritis, peritonitis, intraperitoneal abscess, cholecystitis, cholangitis, liver abscess, deep skin infections, lymphangitis / lymphadenitis, secondary infections such as those caused by trauma, burns, and surgical wounds, urinary tract infections, genital infections, eye infections, and dental infections. [Item A72] A pharmaceutical composition comprising a β-lactam drug, wherein the pharmaceutical composition is administered together with a compound according to any one of Items A1 to A51 or a pharmaceutically acceptable salt thereof. [Item A73] A method for treating a bacterial infection, comprising administering to a patient in need of treatment a therapeutically effective amount of the compound according to any one of Items A1 to A51 or a pharmaceutically acceptable salt thereof.[Item A74] The method according to Item A73, wherein the bacterial infection is a bacterial infection involving a bacterium capable of possessing β-lactamase. [Item A75] The method according to Item A73 or A74, wherein the bacterial infection is sepsis, febrile neutropenia, bacterial meningitis, bacterial endocarditis, otitis media, sinusitis, pneumonia, lung abscess, empyema, secondary infection of a chronic respiratory lesion, pharyngitis / laryngitis, tonsillitis, osteomyelitis, arthritis, peritonitis, intra-abdominal abscess, cholecystitis, cholangitis, liver abscess, deep skin infection, lymphangitis / lymphadenitis, secondary infection of trauma / burn, surgical wound, etc., urinary tract infection, genital infection, eye infection, or dental infection. [Item A76] The method according to any one of Items A73 to A75, wherein the method is administered together with an additional drug.

[0010] The present invention also provides the following: [Item 1] Formula (1a) or (1b): [In formulas (1a) and (1b), G represents an oxygen atom, a sulfur atom, or —NR ａ１ -, X is a hydroxyl group, an optionally substituted C １－６ an alkoxy group, or —NR ａ２ R ｂ１ and R ａ１ , R ａ２ and R ｂ１ are each independently the same or different and are each independently selected from the group consisting of: 1) a hydrogen atom, 2) C １－６ an alkyl group; 3) C ３－１０ Alicyclic group, 4)C ６－１０ aryl 5) 5- or 6-membered heteroaryl; 6) 4- to 10-membered non-aryl heterocycle; 7) C １－６ Alkylcarbonyl group, 8) C ３－１０ 9) an alicyclic carbonyl group, C ６－１０ 10) an arylcarbonyl group, 11) a 5- or 6-membered heteroarylcarbonyl group, １－６ an alkylsulfonyl group, 12) C ３－１０ alicyclic sulfonyl group, 13) C ６－１０ 14) an arylsulfonyl group, 15) a 5- or 6-membered heteroarylsulfonyl group, or 16) an -OR ｃ１ (However, each of the substituents in 2) to 14) above may be substituted), wherein Rａ２ and R ｂ１ may be joined together to form an optionally substituted 4- to 10-membered nitrogen-containing non-aryl heterocycle, R ｃ１ is 1) a hydrogen atom, 2) C １－６ an alkyl group; 3) C ３－１０ Alicyclic group, 4)C ６－１０ 5) aryl, 5) 5- or 6-membered heteroaryl, or 6) 4- to 10-membered non-aryl heterocycle (provided that each of the substituents in 2) to 6) above may be substituted), L １ represents a single bond, an oxygen atom, a sulfur atom, -SO-, -SO ２ -, -NR ｄ -, -NR ｄ C(=O)- or -NR ｄ SO ２ - and L ２ represents a single bond or an optionally substituted C １－６ an alkylene group, and Z is 1) a hydrogen atom, 2) a hydroxyl group, 3) a cyano group, 4) a carboxyl group, 5) C ３－１０ Alicyclic group, 6)C ６－１０ aryl, 7) 5- or 6-membered heteroaryl, 8) 4- to 10-membered non-aryl heterocycle, 9) C １－６ 10) an alkoxy group; ３－１０ 11) an alicyclic oxy group, ６－１０ 12) an aryloxy group, 13) a 4- to 10-membered non-aryl heterocyclic oxy group, 14) C １－６ Alkylthio group, 15) C ３－１０ alicyclic thio group, 16) C ６－１０ 17) an arylthio group, 18) a 4- to 10-membered non-aryl heterocyclic thio group (provided that each of the substituents in 5) to 18) above may be substituted). 19) —SO ２ -NR ｅ１ R ｆ１ , 20)-NR ｅ１ -C(=O)OR ｆ１ , 21)-NR ｇ１ -C(=O)NR ｅ１ R ｆ１ , 22)-NRｅ１ -C(=S)R ｆ１ 、 23)-NR ｅ１ -C(=S)OR ｆ１ 、 24)-NR ｇ１ -C(=S)NR ｅ１ R ｆ１ 、 25)-NR ｇ１ -CR ｅ１ (=NR ｆ１ )、 26)-NR ｇ１ -CR ｅ１ (=N-OR ｆ１ )、 27)-NR ｈ１ -C(=NR ｇ１ )NR ｅ１ R ｆ１ 、 28)-NR ｈ１ -C(=N-OR ｇ１ )NR ｅ１ R ｆ１ 、 29)-NR ｉ１ -C(=NR ｈ１ )NR ｇ１ -NR ｅ１ R ｆ１ 、 30)-NR ｉ１ -C(=N-OR ｈ１ )NR ｇ１ -NR ｅ１ R ｆ１ 、 31)-NR ｅ１ -SO ２ -R ｆ１ 、 32)-NR ｇ１ -SO ２ -NR ｅ１ R ｆ１ 、 33)-C(=O)OR ｅ１ 、 34)-C(=S)OR ｅ１ 、 35)-C(=S)NR ｅ１ R ｆ１ 、 36)-C(=S)NR ｅ１ OR ｆ１ 、 37)-C(=S)NR ｇ１ -NR ｅ１ R ｆ１ 、 38)-C(=NR ｅ１ )R ｆ１ 、 39)-C(=N-OR ｅ１ )R ｆ１ 、 40)-C(=NR ｈ１ )NR ｇ１ -NR ｅ１R ｆ１ , 41)-C(=N-OR ｈ１ ) NR ｇ１ -NR ｅ１ R ｆ１ , 42)-NR ｅ１ R ｆ１ , 43)-NR ｇ１ -NR ｅ１ R ｆ１ , 44)-NR ｅ１ OR ｆ１ , 45)-NR ｅ１ -C(=O)R ｆ１ , 46)-C(=O)NR ｅ１ R ｆ１ , 47)-C(=O)NR ｅ１ OR ｆ１ , 48)-C(=O)NR ｇ１ -NR ｅ１ R ｆ１ , 49)-C(=O)R ｅ１ , 50)-C(=NR ｇ１ ) NR ｅ１ R ｆ１ , or 51)-C(=N-OR ｈ１ ) NR ｅ１ R ｆ１ R １ , R ２ and R ３ Any one of the following formula (2): [In formula (2), Y represents an oxygen atom, a sulfur atom, or —NR ｊ -, ring A is an optionally substituted 4- to 20-membered non-aryl heterocycle, L ３ is -C(=O)-, -S(=O)-, or -S(=O) ２ - and L ４ is 1) a single bond, 2) C １－６ an alkylene group; 3) C ３－１０ 4) a cycloalkylene group, ６－１０ arylene group 5) a 5- or 6-membered heteroarylene group, or 6) a 4- to 10-membered non-aryl heterocyclylene group, 7) —C(═N—OR ｈ１ )-(wherein each of the substituents 2) to 6) above may be substituted), R ５ is 1) a hydrogen atom, 2) C１－６ an alkyl group; 3) C ３－１０ alicyclic group, 4) 4- to 10-membered non-aryl heterocycle, 5) C ６－１０ aryl, 6) 5- or 6-membered heteroaryl, 7) C １－６ an alkylthio group, or (provided that each of the substituents in 2) to 7) above may be substituted); 8) —NR ｅ１ OH], and (R １ , R ２ and R ３ the remaining two are the same or different and independently represent a hydrogen atom, a halogen atom, an optionally substituted C １－６ alkyl group, optionally substituted C １－６ an alkoxy group, optionally substituted C １－６ an alkylthio group, an optionally substituted 5- or 6-membered heteroaryl, or —NR ａ３ R ｂ２ and R ｄ , R ｅ１ , R ｅ２ , R ｆ１ , R ｆ２ , R ｇ１ , R ｇ２ , R ｈ１ , R ｈ２ , R ｉ１ , R ｉ２ and R ｊ are each independently the same or different and represent a hydrogen atom, an optionally substituted C １－６ alkyl group, optionally substituted C ３－１０ Alicyclic group, optionally substituted C ６－１０ aryl, an optionally substituted 5- or 6-membered heteroaryl, or an optionally substituted 4- to 10-membered non-aryl heterocycle; R ｅ１ and R ｆ１ or R ｅ２ and R ｆ２ When the combination of R is bonded to the same nitrogen atom, they may be joined together to form an optionally substituted 4- to 10-membered nitrogen-containing non-aryl heterocycle, ４ 1) -C(=O)R ８ , 2)-SO ２-L ６ -R ８ (above 1) and 2) in the formula, R ８ is -NR ａ５ R ｂ４ , -NR ａ５ -L ７ -B(OR ｍ１ ) ２ , -OR ｍ１ or optionally substituted C １－６ is an alkyl group, and L ６ represents a single bond or -NR ａ６ -), 3) -NR ａ４ R ｂ３ , 4)-B(OR ｍ１ ) ２ , 5)-PO(OR ｍ１ ) (OR ｍ２ 6) an optionally substituted 5-membered heteroaryl, 7) an optionally substituted 5-membered non-aryl heterocycle, or 8) a bioisostere of any of 1) to 7) (provided that the formulae 2), 4), 5) and 6) above include carboxylic acid equivalents, and 8) may include these in duplicate), R ａ３ , R ａ４ , R ａ５ , R ａ６ , R ｂ２ , R ｂ３ and R ｂ４ are each independently the same or different and represent the R ａ１ , R ａ２ and R ｂ１ where R ａ３ and R ｂ２ , R ａ４ and R ｂ３ or R ａ５ and R ｂ４ When a combination of R is bonded to the same nitrogen atom, they may be joined together to form an optionally substituted 4- to 10-membered nitrogen-containing non-aryl heterocycle, ｍ１ is 1) a hydrogen atom, 2) C １－６ an alkyl group; 3) C ３－１０ Alicyclic group, 4)C ６－１０5) aryl, 5) 5- or 6-membered heteroaryl, or 6) 4- to 10-membered non-aryl heterocycle (provided that each of the substituents in 2) to 6) above may be substituted), provided that R ｍ１ is bonded to the boron atom via an oxygen atom, two R ｍ１ is C ２－４ The alkylene may be taken together with the boron atom and two oxygen atoms to form a 5- to 7-membered non-aryl heterocycle (the alkylene portion of the non-aryl heterocycle may be substituted), and R ｍ２ represents a hydrogen atom, an optionally substituted C １－６ an alkyl group or an optionally substituted C ３－１０ is an alicyclic group, ７ is an optionally substituted C １－３ [Item 2] A compound represented by the formula: [wherein L is an alkylene group] or a pharmaceutically acceptable salt thereof. １ represents a single bond, a sulfur atom, or -NR ｄ C(=O)- or -NR ｄ SO ２ - and L ２ represents a single bond or an optionally substituted C １－６ an alkylene group, Z being 1) a hydrogen atom, 2) a hydroxyl group, 3) C ３－１０ Alicyclic group, 4)C ６－１０ aryl, 5) 5- or 6-membered heteroaryl, 6) 4- to 10-membered non-aryl heterocycle, 7) —C(═N—OR ｅ１ ) R ｆ１ , or 8) -NR ｅ１ R ｆ１ [Item 3] The compound according to Item 1, or a pharmaceutically acceptable salt thereof, ２ -L １ is a hydrogen atom, optionally substituted C １－６ an alkyl group or an optionally substituted C １－６ [Item 4] The compound according to item 1 or 2, or a pharmaceutically acceptable salt thereof, wherein Z-L is an alkylthio group. ２ -L １[Item 5] The compound or a pharmaceutically acceptable salt thereof according to any one of the preceding items, wherein G is a hydrogen atom. [Item 6] The compound or a pharmaceutically acceptable salt thereof according to any one of the preceding items, wherein X is a hydroxyl group or an optionally substituted C １－６ [Item 7] The compound according to any one of the preceding items, wherein X is an alkoxy group, or a pharmaceutically acceptable salt thereof. [Item 8] The compound according to any one of the preceding items, wherein X is a hydroxyl group, or a pharmaceutically acceptable salt thereof. [Item 9] The compound according to any one of the preceding items, wherein X is a hydroxyl group, or a pharmaceutically acceptable salt thereof. [Item 10] The compound according to any one of the preceding items, wherein X is a hydroxyl group, or a pharmaceutically acceptable salt thereof. [Item 11] The compound according to any one of the preceding items, wherein X is a hydroxyl group, or a pharmaceutically acceptable salt thereof. [In formulas (3a) and (3b), X, R １ , R ２ and R ３ is as defined in any one of the preceding paragraphs, and R ４ is 1)-COOR ｍ１ (where R ｍ１ is a hydrogen atom, C １－６ Alkyl group, C ３－１０ Alicyclic group, C ６－１０ aryl, 5- or 6-membered heteroaryl, or 4- to 10-membered non-aryl heterocycle, wherein said C １－６ Alkyl group, ３－１０ alicyclic group, said C ６－１０ 1) a compound according to any one of the preceding items, or a pharmaceutically acceptable salt thereof, wherein R is selected from the group consisting of: ４ [Item 10] The compound according to item 8, or a pharmaceutically acceptable salt thereof, wherein the compound of formula (1a) and (1b) or the compound of formula (3a) and (3b) is a compound of the following formula (4a) and (4b), respectively: [In formulas (4a) and (4b), X, R ４ , Y, Ring A, L ３ , L ４ , and R ５is as defined in any one of the preceding paragraphs, and R １ and R ２ are each independently the same or different and represent a hydrogen atom, a halogen atom, or C １－６ Alkyl group, C １－６ Alkoxy group (provided that the C １－６ The alkyl group and the C １－６ [Item 11] The compound according to any one of the above items, wherein ring A is an optionally substituted 4- to 10-membered non-aryl heterocycle, or a pharmaceutically acceptable salt thereof. [Item 12] The compound according to any one of the above items, wherein ring A is an optionally substituted 4- to 7-membered non-aryl heterocycle, or a pharmaceutically acceptable salt thereof. [Item 13] The compound according to any one of the above items, wherein Y is an oxygen atom or a sulfur atom, or a pharmaceutically acceptable salt thereof. [Item 14] The compound according to any one of the above items, wherein Y is an oxygen atom, or a pharmaceutically acceptable salt thereof. [Item 15] The compound of formula (1a) and (1b), the compound of formula (3a) and (3b), or the compound of formula (4a) and (4b) is represented by the following formula (5a) and (5b), respectively: [In formulas (5a) and (5b), ring A is an optionally substituted 4- to 6-membered nitrogen-containing non-aryl heterocycle], or a pharmaceutically acceptable salt thereof. [Item 16] L ３ is -C(=O)- or -S(=O) ２ [Item 17] The compound according to any one of the preceding items, wherein L is -, or a pharmaceutically acceptable salt thereof. ３ [Item 18] The compound according to any one of the preceding items, wherein L is —C(═O)—, or a pharmaceutically acceptable salt thereof. ４ is a single bond, -C(=N-OR ｈ１ )- or optionally substituted C １－６ an alkylene group, where R ｈ１ is optionally substituted C １－６[Item 19] The compound according to any one of the above items, wherein R is an alkyl group, or a pharmaceutically acceptable salt thereof. １ and R ２ are each independently the same or different and are each independently selected from the group consisting of: 1) a hydrogen atom, 2) a halogen atom, 3) C １－６ 4) an alkyl group; １－６ an alkoxy group, and 5) C １－６ [Item 20] The compound according to any one of the above items, wherein R is selected from the group consisting of an alkylthio group (wherein each of the substituents in 3) to 5) above may be substituted), or a pharmaceutically acceptable salt thereof. １ and R ２ are each independently the same or different and are each independently selected from the group consisting of: 1) a hydrogen atom, 2) a halogen atom, 3) an optionally substituted C １－６ [Item 21] The compound according to any one of the preceding items, wherein R is selected from the group consisting of an alkyl group and an alkyl group. １ and R ２ and (3a) and (3b) are each a hydrogen atom. [Item 22] The compound according to any one of the preceding items, or a pharmaceutically acceptable salt thereof, wherein the compounds of formulas (1a) and (1b), or the compounds of formulas (3a) and (3b), or the compounds of formulas (4a) and (4b), or the compounds of formulas (5a) and (5b) are each a hydrogen atom. [In formulas (6a) and (6b), L ３ , L ４ , and R ５ [Item 23] The compound according to any one of the above items, or a pharmaceutically acceptable salt thereof, wherein m is 1 or 2, n is 1 or 2, and m+n is 2 or 3. [Item 24] The compound according to any one of the above items, or a pharmaceutically acceptable salt thereof, wherein m is 1 and n is 1. [Item 25] L ４ is a single bond or -NR ２１R ２２ Or = NOR ２３ C optionally substituted with １－６ an alkylene group, where R ２１ , R ２２ and R ２３ are each independently a hydrogen atom, an optionally substituted C １－６ [Item 26] The compound according to any one of the preceding items, wherein L is an alkyl group or an optionally substituted 4- to 10-membered non-aryl heterocyclic carbonyl group, or a pharmaceutically acceptable salt thereof. ４ is a single bond, -CH ２ -, -CH(NH ２ ) -, or -CH(NH ２ )-CH ２ -, where L ４ When an amino group is present in the ３ [Item 27] ​​The compound according to any one of the preceding items, or a pharmaceutically acceptable salt thereof, which binds to ４ is a single bond, -CH ２ -, -CMe(NH ２ )-, -CH(NHMe)-, -CD(NH ２ )-(wherein D represents a deuterium atom), -CH(NH ２ ) - or -CH ２ CH ２ [Item 28] The compound according to any one of the preceding items, wherein L is -, or a pharmaceutically acceptable salt thereof. ４ is a single bond, -CH ２ -, or -CH(NH ２ 29. The compound according to any one of the preceding items, wherein R is 1 or 2; or a pharmaceutically acceptable salt thereof. ５ represents a hydrogen atom, an optionally substituted C １－６ an alkyl group, an optionally substituted 4- to 10-membered non-aryl heterocycle, an optionally substituted C ６－１０ Aryl, optionally substituted 5- or 6-membered heteroaryl, optionally substituted C １－６ an alkylthio group, or —NR ｅ１ OH, where R ｅ１represents a hydrogen atom or an optionally substituted C １－６ [Item 30] The compound according to any one of the preceding items, wherein R is an alkyl group, or a pharmaceutically acceptable salt thereof. ５ is an optionally substituted 5- or 6-membered heteroaryl or an optionally substituted C ６－１０ [Item 31] The compound according to any one of the preceding items, wherein R is aryl, or a pharmaceutically acceptable salt thereof. ５ [Item 32] The compound according to any one of the preceding items, wherein R is an optionally substituted 5- or 6-membered heteroaryl, or a pharmaceutically acceptable salt thereof. ５ [Item 33] The compound according to any one of the preceding items, wherein L is an optionally substituted 4- to 10-membered non-aryl heterocycle, or a pharmaceutically acceptable salt thereof. ４ is a single bond, and R ５ is -NR ｅ１ OH, where R ｅ１ represents a hydrogen atom or an optionally substituted C １－６ [Item 34] The compound according to any one of the above items, or a pharmaceutically acceptable salt thereof, wherein L is an alkyl group. ４ is 1)-(CH ２ ) ｐ -CR １０ (N.H.R. １１ ) -, 2) -(CH ２ ) ｑ -CR １２ R １３ -, or 3)-(CH ２ ) ｐ -CR １０ (N.H.R. １１ )-(CH ２ ) ｑ -CR １２ R １３ - (wherein p and q are independently 0 or 1); R １０ is 1) a hydrogen atom, 2) a carboxyl group, 3) -C(=O)NR １０ａ R １０ｂ and R １１ is 1) a hydrogen atom, 2) -C(=O)R １１ａor 3) an optionally substituted 5- or 6-membered non-aryl heterocyclic carbonyl group, provided that R １０ -C(=O)NR １０ａ R １０ｂ When R １０ｂ and R １１ Let's get together -CH ２ CH ２ - may be formed, R １２ is 1) a hydrogen atom, or 2) an optionally substituted C １－４ is an alkyl group, R １３ is 1) a hydrogen atom, 2) a hydroxyl group, or 3) an optionally substituted C １－４ 4) an alkyl group, 5) a sulfanyl group, 6) an optionally substituted C １－４ an alkylthio group, 7) —NR １３ａ R １３ｂ , 8)-NR １３ａ -C(=O)R １３ｂ 9) an optionally substituted 5- or 6-membered non-aryl heterocyclic carbonylamino group; 10) —NR １３ａ -C(=O)NR １３ｂ R １３ｃ , 11)-C(=O)NR １３ａ R １３ｂ , 12)-C(=O)NR １３ａ OR １３ｂ , 13)-S(=O) ２ -R １３ａ , 14)-S(=O) ２ -NR １３ａ R １３ｂ , 15)-C(=O)NR １３ａ -S(=O) ２ -R １３ｂ or 16) -C(=O)NR １３ａ -S(=O) ２ -NR １３ｂ R １３ｃ and R １０ａ , R １０ｂ , R １１ａ , R １３ａ , R １３ｂ and R １３ｃ are each independently a hydrogen atom or an optionally substituted C １－４[Item 35] The compound according to any one of the preceding items, or a pharmaceutically acceptable salt thereof, wherein R is an alkyl group. ５ represents a hydrogen atom or an optionally substituted C １－４ [Item 36] The compound according to any one of the preceding items, or a pharmaceutically acceptable salt thereof, wherein R is an alkyl group. ５ is as follows: and the subscript d is selected from the group consisting of R ５ is the number of substitutable positions on the ring of each R ６ａ are independently: 1) a hydrogen atom, 2) a hydroxyl group, 3) a cyano group, 4) a nitro group, 5) a halogen, 6) C １－４ 7) an alkyl group, ３－１０ Alicyclic group, 8)C １－４ 9) an alkoxy group; ３－１０ 10) an alicyclic oxy group, ６－１０ 11) an aryloxy group, 12) a 4- to 10-membered non-aryl heterocyclic oxy group (provided that each of the substituents in 6) to 12) above may be substituted), 13) —SO ２ -NR ｅ２ R ｆ２ , 14)-NR ｇ２ -CR ｅ２ (=NR ｆ２ ), 15)-NR ｇ２ -CR ｅ２ (=N-OR ｆ２ ), 16)-NR ｈ２ -C(=NR ｇ２ ) NR ｅ２ R ｆ２ , 17)-NR ｈ２ -C(=N-OR ｇ２ ) NR ｅ２ R ｆ２ , 18)-NR ｉ２ -C(=NR ｈ２ ) NR ｇ２ -NR ｅ２ R ｆ２ , 19)-NR ｉ２ -C(=N-OR ｈ２ ) NR ｇ２ -NR ｅ２ R ｆ２, 20)-C(=NR ｅ２ ) R ｆ２ , 21)-C(=N-OR ｅ２ ) R ｆ２ , 22)-C(=NR ｈ２ )-NR ｅ２ R ｆ２ , 23)-C(=NR ｈ２ ) NR ｇ２ -NR ｅ２ R ｆ２ , 24)-C(=N-OR ｈ２ ) NR ｇ２ -NR ｅ２ R ｆ２ , 25)-NR ｅ２ R ｆ２ , 26)-NR ｇ２ -NR ｅ２ R ｆ２ , 27)-NR ｅ２ OR ｆ２ , 28)-NR ｅ２ -C(=O)R ｆ２ , 29)-C(=O)NR ｅ２ R ｆ２ , 30)-C(=O)NR ｅ２ OR ｆ２ , 31)-C(=O)NR ｇ２ -NR ｅ２ R ｆ２ , 32)-C(=O)R ｅ２ , 33)-C(=O)OR ｅ２ , and 34)-C(=N-OR ｈ２ ) NR ｅ２ R ｆ２ and each R is selected from the group consisting of ６ｂ are independently: 1) a hydrogen atom; 2) a hydroxyl group; 3) C １－４ an alkyl group (wherein the alkyl group may be substituted); 4) C ３－１０ an alicyclic group, (however, the alicyclic group may be substituted); 5) —C(═NR ｅ２ ) R ｆ２ , 6)-C(=N-OR ｅ２ ) R ｆ２ , 7)-SO ２ -NR ｅ２ R ｆ２ , 8)-C(=NR ｈ２ )-NR ｅ２ Rｆ２ , 9)-C(=NR ｈ２ ) NR ｇ２ -NR ｅ２ R ｆ２ , 10)-C(=N-OR ｈ２ ) NR ｇ２ -NR ｅ２ R ｆ２ , 11)-C(=O)NR ｅ２ R ｆ２ , 12)-C(=O)NR ｅ２ OR ｆ２ , 13)-C(=O)NR ｇ２ -NR ｅ２ R ｆ２ , 14)-C(=O)R ｅ２ , and 15)-C(=N-OR ｈ２ ) NR ｅ２ R ｆ２ [Item 37] The compound according to any one of items 1 to 31, or a pharmaceutically acceptable salt thereof, selected from the group consisting of: ５ is as follows: and the subscript d is a 5- or 6-membered aryl or heteroaryl selected from the group consisting of R ５ is the number of substitutable positions on the ring of each R ６ａ are independently: 1) a hydrogen atom, 2) a hydroxyl group, 3) a halogen, 4) C １－４ an alkyl group, wherein the alkyl group is NR ｅ２ R ｆ２ , a 5- or 6-membered non-aryl heterocycle, —C(═O)OR ｆ２ or may be substituted with a hydroxyl group) 5) C １－４ Alkoxy group 6) -NR ｅ２ R ｆ２ , and 7) —C(═O)OR ｅ２ and each R is selected from the group consisting of ６ｂ are independently: 1) a hydrogen atom, 2) a hydroxyl group, and 3) C １－４ an alkyl group, wherein the alkyl group is NR ｅ２ R ｆ２ , —C(═O)NR ｅ２ R ｆ２ , -C(=O)OR ｆ２[Item 38] The compound according to any one of Items 1 to 31 and 36, or a pharmaceutically acceptable salt thereof, wherein R is selected from the group consisting of ｅ２ and R ｆ２ are each independently the same or different and represent a hydrogen atom, an optionally substituted C １－６ an alkyl group or an optionally substituted C ３－１０ [Item 39] The compound according to any one of Items 1 to 31, 36 and 37, or a pharmaceutically acceptable salt thereof, wherein R is an alicyclic group. ｅ２ and R ｆ２ are each independently the same or different and represent a hydrogen atom or an optionally substituted C １－６ [Item 40] The compound according to any one of items 1 to 31 and items 36 to 38, or a pharmaceutically acceptable salt thereof, wherein R is an alkyl group. ｅ２ and R ｆ２ [Item 41] The compound or a pharmaceutically acceptable salt thereof according to any one of Items 1 to 31 and Items 36 to 39, wherein R is a hydrogen atom. ６ａ is -NR ｅ２ R ｆ２ and R ｅ２ and R ｆ２ is a hydrogen atom on one side and a C atom on the other side. １－４ [Item 42] The compound according to any one of Items 36 to 39, wherein R is an alkyl group (provided that the alkyl group may be substituted with an amino group or a hydroxyl group), or a pharmaceutically acceptable salt thereof. ５ is as follows: and the subscript d is a 4-6 membered non-aryl heterocycle selected from the group consisting of R ５ is the number of substitutable positions on the ring of each R ７ａ are independently: 1) a hydrogen atom, 2) a hydroxyl group, 3) a cyano group, 4) a halogen, 5) C １－４ 6) an alkyl group, ３－１０ Alicyclic group, 7)C １－４ an alkoxy group, 8) C ３－１０ 9) an alicyclic oxy group, C ６－１０10) an aryloxy group, 11) a 4- to 10-membered non-aryl heterocyclic oxy group, (provided that each of the substituents in 5) to 11) above may be substituted). 12) —SO ２ -NR ｅ３ R ｆ３ , 13)-NR ｇ２ -CR ｅ３ (=NR ｆ３ ), 14)-NR ｇ２ -CR ｅ３ (=N-OR ｆ３ ), 15)-NR ｈ２ -C(=NR ｇ２ ) NR ｅ３ R ｆ３ , 16)-NR ｈ２ -C(=N-OR ｇ２ ) NR ｅ３ R ｆ３ , 17)-NR ｉ２ -C(=NR ｈ２ ) NR ｇ２ -NR ｅ３ R ｆ３ , 18)-NR ｉ２ -C(=N-OR ｈ２ ) NR ｇ２ -NR ｅ３ R ｆ３ , 19)-C(=NR ｅ３ ) R ｆ３ , 20)-C(=N-OR ｅ３ ) R ｆ３ , 21)-C(=NR ｈ２ )-NR ｅ３ R ｆ３ , 22)-C(=NR ｈ２ ) NR ｇ２ -NR ｅ３ R ｆ３ , 23)-C(=N-OR ｈ２ ) NR ｇ２ -NR ｅ３ R ｆ３ , 24)-NR ｅ３ R ｆ３ , 25)-NR ｇ２ -NR ｅ３ R ｆ３ , 26)-NR ｅ３ OR ｆ３ , 27)-NR ｅ３ -C(=O)Rｆ３ , 28)-C(=O)NR ｅ３ R ｆ３ , 29)-C(=O)NR ｅ３ OR ｆ３ , 30)-C(=O)NR ｇ２ -NR ｅ３ R ｆ３ , 31)-C(=O)R ｅ３ , 32)-C(=O)OR ｅ３ , and 33)-C(=N-OR ｈ２ ) NR ｅ３ R ｆ３ and each R is selected from the group consisting of ７ｂ are independently: 1) a hydrogen atom; 2) a hydroxyl group; 3) C １－４ an alkyl group (wherein the alkyl group may be substituted); 4) C ３－１０ an alicyclic group, (however, the alicyclic group may be substituted); 5) —C(═NR ｅ３ ) R ｆ３ , 6)-C(=N-OR ｅ３ ) R ｆ３ , 7)-SO ２ -NR ｅ３ R ｆ３ , 8)-C(=NR ｈ２ )-NR ｅ３ R ｆ３ , 9)-C(=NR ｈ２ ) NR ｇ２ -NR ｅ３ R ｆ３ , 10)-C(=N-OR ｈ２ ) NR ｇ２ -NR ｅ３ R ｆ３ , 11)-C(=O)NR ｅ３ R ｆ３ , 12)-C(=O)NR ｅ３ OR ｆ３ , 13)-C(=O)NR ｇ２ -NR ｅ３ R ｆ３ , 14)-C(=O)R ｅ３ , and 15)-C(=N-OR ｈ２ ) NR ｅ３ R ｆ３ R is selected from the group consisting of ｅ３ and R ｆ３ is R according to item 1ｅ２ and R ｆ２ [Item 43] The compound according to any one of Items 1 to 29 and 32, or a pharmaceutically acceptable salt thereof, wherein R ５ is as follows: and the subscript d is a 4-6 membered non-aryl heterocycle selected from the group consisting of R ５ is the number of substitutable positions on the ring of each R ７ａ are independently: 1) a hydrogen atom, 2) a hydroxyl group, 3) a halogen, 4) C １－４ an alkyl group, wherein the alkyl group is NR ｅ３ R ｆ３ , a 5- or 6-membered non-aryl heterocycle, —C(═O)OR ｆ３ or may be substituted with a hydroxyl group) 5) C １－４ Alkoxy group 6) -NR ｅ３ R ｆ３ , 7)-C(=O)OR ｅ３ , and 8) C ６－１０ Aryl 9) —C(═O)NR ｅ３ R ｆ３ and each R is selected from the group consisting of ７ｂ are independently: 1) a hydrogen atom, 2) a hydroxyl group, and 3) C １－４ an alkyl group, wherein the alkyl group is NR ｅ３ R ｆ３ , -C(=O)OR ｆ３ or a hydroxyl group), and R ｅ３ and R ｆ３ is R according to any one of items 38 to 40. ｅ２ and R ｆ２ [Item 44] The compound according to any one of Items 1 to 29, 32, and 42, or a pharmaceutically acceptable salt thereof, wherein L ４ -CH(NH ２ )-CHR １３ -, and the NH ２ The carbon bonded to L ３ and R ５ is a hydrogen atom, and R １３ 1) -NH-C(=O)CH ３ , 2)-NH-C(=O)NH２ , 3)-NH-C(=O)CH(NH ２ )-CH ２ C(=O)NH ２ , 4)-NH-C(=O)CH ２ -NH ２ , 5)-NH-C(=O)CH(NH ２ )-CH ２ 45) The compound according to any one of the preceding items, or a pharmaceutically acceptable salt thereof, wherein L is OH, or 6) a pyrrolidin-2-ylcarbonylamino group. ４ -CH(NH ２ )-CR １２ R １３ -, and the NH ２ The carbon bonded to L ３ and R ５ is a hydrogen atom or methyl, R １２ is a hydrogen atom or methyl, R １３ [Item 46] The compound according to any one of the preceding items, or a pharmaceutically acceptable salt thereof, wherein L is a benzylthio group or a sulfanyl group. ４ -CH(NH ２ )-(CH ２ ) ｑ -CHR １３ -, q is 0 or 1, and the NH ２ The carbon bonded to L ３ and R ５ is a hydrogen atom, and R １３ is: 1) a carboxyl group, 2) -C(=O)NH ２ , 3)-C(=O)NH(CH ３ ), 4)-C(=O)N(CH ３ ) ２ , 5)-C(=O)NH-(CH ２ ) ２ -OH, 6) -C(=O)NH-(CH ２ ) ２ -NH ２ , 7)-C(=O)NH-S(=O) ２ -CH ３ , 8)-C(=O)NHOH, 9)-S(=O) ２ -NH ２, 10)-S(=O) ２ -CH ３ or 11) a hydroxyl group, the compound according to any one of the preceding items or a pharmaceutically acceptable salt thereof. [Item 47] L ４ -CH(NHR １１ )-CH ２ -, and the NHR １１ The carbon bonded to L ３ and R ５ is hydrogen, and R １１ 1) -C(=O)CH(NH ２ )-CH ２ C(=O)NH ２ , 2)-C(=O)CH ２ -NH ２ , 3)-C(=O)CH(CH ３ )-NH ２ , 4)-C(=O)CH(NH ２ )-CH ２ 48) The compound according to any one of the preceding items, or a pharmaceutically acceptable salt thereof, wherein L is 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 63, 64, 65, 66, 67, 68, 69, 70, 71, 72, 73, 74, 75, 76, 77, 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93, 94, 95, 96, 97, 98, 99, 100, 101, 102, 103, 104, 105, 106, 107, 108, 109, 110, 111, 112, 113, 114, 115, 116, 117, 118, 11 ４ -CH(NHR １１ )-CH(COOH)-, and the NHR １１ The carbon bonded to L ３ and R ５ is hydrogen, and R １１ 1) -C(=O)CH(NH ２ )-CH ２ C(=O)NH ２ , 2)-C(=O)CH ２ -NH ２ , 3)-C(=O)CH(CH ３ )-NH ２ , 4)-C(=O)CH(NH ２ )-CH ２ 49) The compound according to any one of the preceding items, or a pharmaceutically acceptable salt thereof, wherein L is 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 63, 64, 65, 66, 67, 68, 69, 70, 71, 72, 73, 74, 75, 76, 77, 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93, 94, 95, 96, 97, 98, 99, 100, 101, 102, 103, 104, 105, 106, 107, 108, 109, 110, 111, 112, 113, 114, 115, 116, 117, 118, 11 ４ Ha-CHR １３ - or -CH ２ -CHR １３ - and R ５is hydrogen, and R １３ is -C(=O)NH ２ or —C(═O)NHOH, or a pharmaceutically acceptable salt thereof. [Item 50] L ４ Ha-CH ２ -CR １０ (NH ２ )-, and the CH ２ The group is L ３ and R ５ is hydrogen, R １０ is a carboxy group or —C(═O)NH ２ [Item 51] The compound according to any one of the preceding items, or a pharmaceutically acceptable salt thereof. ４ Ha-(CH ２ ) ｐ -CR １０ (N.H.R. １１ )-(CH ２ ) ｑ -CHR １３ -or-CHR １３ - (CH ２ ) ｑ -CR １０ (N.H.R. １１ )-(CH ２ ) ｐ -, where q is 0 or 1, R ５ is hydrogen, (1) L ４ Ga-CHR １３ - (CH ２ ) ｑ -CR １０ (N.H.R. １１ )-(CH ２ ) ｐ When -, the -CHR １３ The carbon of the - group is L ３ p is 0, and R １０ represents a hydrogen atom, a carboxyl group, or —C(═O)NHR １０ｂ and R １１ is a hydrogen atom, and R １０ｂ is a hydrogen atom, provided that R １０ -C(=O)NHR １０ｂ When R １０ｂ and R１１ Let's get together -CH ２ CH ２ - may be formed, R １３ is a hydrogen atom; (2) L ４ Ga-(CH ２ ) ｐ -CR １０ (N.H.R. １１ )-(CH ２ ) ｑ -CHR １３ -, the -(CH ２ ) ｐ The carbon of the - group is L ３ p is 1; R １０ and R １１ are both hydrogen atoms, and R １３ represents a carboxyl group or —C(═O)NR １３ａ R １３ｂ and R １３ａ and R １３ｂ are each independently a hydrogen atom or an optionally substituted C １－４ [Item 52] The compound according to any one of the preceding items, or a pharmaceutically acceptable salt thereof, wherein L is an alkyl group. ４ is -CR １２ (NH ２ )- and R １２ is a hydrogen atom or a methyl group, R ５ is a C optionally substituted with one hydroxyl group １－４ Item 53: The compound according to any one of the preceding items, or a pharmaceutically acceptable salt thereof, which is represented by the following compound name or structural formula: 7-[(1-acetylazetidin-3-yl)oxy]-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid. , 8-[(1-acetylazetidin-3-yl)oxy]-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-({1-[(1H-imidazol-5-yl)acetyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 4,4-dihydroxy-8-({1-[(1H-imidazol-5-yl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidiabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-{[1-(methanesulfonyl)azetidin-3-yl]oxy}-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 4,4-dihydroxy-8-{[1-(methanesulfonyl)azetidin-3-yl]oxy}-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 7-({1-[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 8-({1-[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 7-({1-[(2-amino-1,3-thiazol-4-yl)(methoxyimino)acetyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 8-({1-[(2-amino-1,3-thiazol-4-yl)(methoxyimino)acetyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-{[1-(pyridine-2-carbonyl)azetidin-3-yl]oxy}-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 4,4-dihydroxy-8-{[1-(pyridine-2-carbonyl)azetidin-3-yl]oxy}-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-({1-[(methylsulfanyl)acetyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 4,4-dihydroxy-8-({1-[(methylsulfanyl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-{[1-(1H-1,2,4-triazole-3-carbonyl)azetidin-3-yl]oxy}-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 4,4-dihydroxy-8-{[1-(1H-1,2,4-triazole-3-carbonyl)azetidin-3-yl]oxy}-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-{[1-(1-oxido-2-pyridinylcarbonyl)azetidin-3-yl]oxy}-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 4,4-dihydroxy-8-{[1-(1-oxido-2-pyridinylcarbonyl)azetidin-3-yl]oxy}-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 7-({1-[(2R)-2-amino-2-phenylacetyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 8-({1-[(2R)-2-amino-2-phenylacetyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 7-[(1-benzoylazetidin-3-yl)oxy]-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid , 8-[(1-benzoylazetidin-3-yl)oxy]-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-{[1-(pyridine-3-carbonyl)azetidin-3-yl]oxy}-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 4,4-dihydroxy-8-{[1-(pyridine-3-carbonyl)azetidin-3-yl]oxy}-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-({1-[(pyridin-2-yl)acetyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 4,4-dihydroxy-8-({1-[(pyridin-2-yl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-({1-[(pyridin-3-yl)acetyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 4,4-dihydroxy-8-({1-[(pyridin-3-yl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 7-({1-[(2S)-2-amino-2-phenylacetyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 8-({1-[(2S)-2-amino-2-phenylacetyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-({1-[(pyridin-4-yl)acetyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 4,4-dihydroxy-8-({1-[(pyridin-4-yl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-({1-[(4-hydroxyphenyl)acetyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 4,4-dihydroxy-8-({1-[(4-hydroxyphenyl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-({1-[(1H-1,2,4-triazol-1-yl)acetyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 4,4-dihydroxy-8-({1-[(1H-1,2,4-triazol-1-yl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 7-({1-[amino(1H-imidazol-5-yl)acetyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 8-({1-[amino(1H-imidazol-5-yl)acetyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidiabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-{[1-(phenylacetyl)azetidin-3-yl]oxy}-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 4,4-dihydroxy-8-{[1-(phenylacetyl)azetidin-3-yl]oxy}-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-{[1-(3-phenylpropanoyl)azetidin-3-yl]oxy}-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 4,4-dihydroxy-8-{[1-(3-phenylpropanoyl)azetidin-3-yl]oxy}-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-({1-[(1H-imidazol-1-yl)acetyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 4,4-dihydroxy-8-({1-[(1H-imidazol-1-yl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidiabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-({1-[(1H-tetrazol-1-yl)acetyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 4,4-dihydroxy-8-({1-[(1H-tetrazol-1-yl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-({1-[(2H-tetrazol-5-yl)acetyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 4,4-dihydroxy-8-({1-[(2H-tetrazol-5-yl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-[(1-D-phenylalanylazetidin-3-yl)oxy]-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid , 4,4-dihydroxy-8-[(1-D-phenylalanylazetidin-3-yl)oxy]-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-[(1-D-tyrosylazetidin-3-yl)oxy]-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid , 4,4-dihydroxy-8-[(1-D-tyrosylazetidin-3-yl)oxy]-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 7-[(1-D-histidylazetidin-3-yl)oxy]-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid , 8-[(1-D-histidylazetidin-3-yl)oxy]-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-[(1-D-valylazetidin-3-yl)oxy]-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid , 4,4-dihydroxy-8-[(1-D-valylazetidin-3-yl)oxy]-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 7-[(1-L-histidylazetidin-3-yl)oxy]-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid , 8-[(1-L-histidylazetidin-3-yl)oxy]-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 7-[(1-{(2R)-2-[(4-ethyl-2,3-dioxopiperazine-1-carbonyl)amino]-2-phenylacetyl}azetidin-3-yl)oxy]-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 8-[(1-{(2R)-2-[(4-ethyl-2,3-dioxopiperazine-1-carbonyl)amino]-2-phenylacetyl}azetidin-3-yl)oxy]-4,4-dihydroxy-5-oxa-4-boranuidiabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-[(1-D-prolylazetidin-3-yl)oxy]-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid , 4,4-dihydroxy-8-[(1-D-prolylazetidin-3-yl)oxy]-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-[(1-L-prolylazetidin-3-yl)oxy]-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid , 4,4-dihydroxy-8-[(1-L-prolylazetidin-3-yl)oxy]-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 7-[(1-{[4-(2-aminoethyl)-1H-imidazol-1-yl]acetyl}azetidin-3-yl)oxy]-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 8-[(1-{[4-(2-aminoethyl)-1H-imidazol-1-yl]acetyl}azetidin-3-yl)oxy]-4,4-dihydroxy-5-oxa-4-boranuidiabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 7-{[1-(3,4-dihydroxybenzoyl)azetidin-3-yl]oxy}-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 8-{[1-(3,4-dihydroxybenzoyl)azetidin-3-yl]oxy}-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-{[1-(hydroxycarbamoyl)azetidin-3-yl]oxy}-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , and 4,4-dihydroxy-8-{[1-(hydroxycarbamoyl)azetidin-3-yl]oxy}-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid [Item 54] The compound according to Item 1, which is represented by the following compound name or structural formula, or a pharmaceutically acceptable salt thereof: 7-({1-[(2R)-2-amino-2-(1H-imidazol-4-yl)acetyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborimine-8-carboxylic acid. , 8-({1-[(2R)-2-amino-2-(1H-imidazol-4-yl)acetyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidiabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 7-({1-[(2S)-2-amino-2-(1H-imidazol-4-yl)acetyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 8-({1-[(2S)-2-amino-2-(1H-imidazol-4-yl)acetyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidiabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 7-({1-[amino(1-methyl-1H-imidazol-4-yl)acetyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 8-({1-[amino(1-methyl-1H-imidazol-4-yl)acetyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidiabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-{[1-(4H-1,2,4-triazole-3-sulfonyl)azetidin-3-yl]oxy}-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 4,4-dihydroxy-8-{[1-(4H-1,2,4-triazole-3-sulfonyl)azetidin-3-yl]oxy}-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 7-({1-[2-amino-2-(1H-imidazol-4-yl)( ２ H) Ethanoyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborimine-8-carboxylic acid , 8-({1-[2-amino-2-(1H-imidazol-4-yl)( ２ H) [Ethanoyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 7-({1-[2-amino-2-(1H-imidazol-4-yl)propanoyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 8-({1-[2-amino-2-(1H-imidazol-4-yl)propanoyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidiabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 7-({(3S)-1-[amino(1H-imidazol-4-yl)acetyl]pyrrolidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 8-({(3S)-1-[amino(1H-imidazol-4-yl)acetyl]pyrrolidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidiabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-{[1-(4-hydroxy-6-methylpyridine-3-carbonyl)azetidin-3-yl]oxy}-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid , 4,4-dihydroxy-8-{[1-(4-hydroxy-6-methylpyridine-3-carbonyl)azetidin-3-yl]oxy}-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 7-({1-[amino(1-methyl-1H-imidazol-5-yl)acetyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborimine-8-carboxylic acid , 8-({1-[amino(1-methyl-1H-imidazol-5-yl)acetyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidiabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 7-[(1-{amino[1-(carboxymethyl)-1H-imidazol-4-yl]acetyl}azetidin-3-yl)oxy]-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 8-[(1-{amino[1-(carboxymethyl)-1H-imidazol-4-yl]acetyl}azetidin-3-yl)oxy]-4,4-dihydroxy-5-oxa-4-boranuidiacyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 7-[(1-{amino[1-(2-amino-2-oxoethyl)-1H-imidazol-4-yl]acetyl}azetidin-3-yl)oxy]-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 8-[(1-{amino[1-(2-amino-2-oxoethyl)-1H-imidazol-4-yl]acetyl}azetidin-3-yl)oxy]-4,4-dihydroxy-5-oxa-4-boranuidiabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 7-({1-[amino(pyridin-3-yl)acetyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 8-({1-[amino(pyridin-3-yl)acetyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 7-({1-[amino(1-methyl-1H-pyrazol-4-yl)acetyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 8-({1-[amino(1-methyl-1H-pyrazol-4-yl)acetyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 7-({(3R)-1-[amino(1H-imidazol-4-yl)acetyl]pyrrolidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 8-({(3R)-1-[amino(1H-imidazol-4-yl)acetyl]pyrrolidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidiacyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 7-({1-[amino(2-methyl-1H-imidazol-4-yl)acetyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborimine-8-carboxylic acid , 8-({1-[amino(2-methyl-1H-imidazol-4-yl)acetyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidiabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 7-({1-[amino(1,3-thiazol-4-yl)acetyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 8-({1-[amino(1,3-thiazol-4-yl)acetyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-{[1-(1H-imidazole-4-sulfonyl)azetidin-3-yl]oxy}-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid , 4,4-dihydroxy-8-{[1-(1H-imidazole-4-sulfonyl)azetidin-3-yl]oxy}-5-oxa-4-boranuidiabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-{[1-(pyridine-3-sulfonyl)azetidin-3-yl]oxy}-3,4-dihydro-2H-1,2-benzoxaborimine-8-carboxylic acid , 4,4-dihydroxy-8-{[1-(pyridine-3-sulfonyl)azetidin-3-yl]oxy}-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-{[1-(1-oxo-1λ ５ -pyridine-2-sulfonyl)azetidin-3-yl]oxy}-3,4-dihydro-2H-1,2-benzoxaborimine-8-carboxylic acid , 4,4-dihydroxy-8-{[1-(1-oxo-1λ ５ -pyridine-2-sulfonyl)azetidin-3-yl]oxy}-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 7-({1-[(2-amino-1,3-thiazol-4-yl)acetyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 8-({1-[(2-amino-1,3-thiazol-4-yl)acetyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 7-{[1-(2-amino-1,3-thiazole-4-carbonyl)azetidin-3-yl]oxy}-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid , 8-{[1-(2-amino-1,3-thiazole-4-carbonyl)azetidin-3-yl]oxy}-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-({1-[(1H-1,2,3-triazol-1-yl)acetyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 4,4-dihydroxy-8-({1-[(1H-1,2,3-triazol-1-yl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 7-[(1-{[1-(2-aminoethyl)-1H-imidazol-4-yl]acetyl}azetidin-3-yl)oxy]-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 8-[(1-{[1-(2-aminoethyl)-1H-imidazol-4-yl]acetyl}azetidin-3-yl)oxy]-4,4-dihydroxy-5-oxa-4-boranuidiacyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-{[1-(1H-imidazole-4-carbonyl)azetidin-3-yl]oxy}-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 4,4-dihydroxy-8-{[1-(1H-imidazole-4-carbonyl)azetidin-3-yl]oxy}-5-oxa-4-boranuidiabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-{[1-(1H-imidazole-2-carbonyl)azetidin-3-yl]oxy}-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 4,4-dihydroxy-8-{[1-(1H-imidazole-2-carbonyl)azetidin-3-yl]oxy}-5-oxa-4-boranuidiabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-[(1-{[4-(hydroxymethyl)-1H-1,2,3-triazol-1-yl]acetyl}azetidin-3-yl)oxy]-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 4,4-dihydroxy-8-[(1-{[4-(hydroxymethyl)-1H-1,2,3-triazol-1-yl]acetyl}azetidin-3-yl)oxy]-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-{[1-({4-[(methylamino)methyl]-1H-1,2,3-triazol-1-yl}acetyl)azetidin-3-yl]oxy}-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 4,4-dihydroxy-8-{[1-({4-[(methylamino)methyl]-1H-1,2,3-triazol-1-yl}acetyl)azetidin-3-yl]oxy}-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-{[1-({4-[(piperazin-1-yl)methyl]-1H-1,2,3-triazol-1-yl}acetyl)azetidin-3-yl]oxy}-3,4-dihydro-2H-1,2-benzoxaborimine-8-carboxylic acid , 4,4-dihydroxy-8-{[1-({4-[(piperazin-1-yl)methyl]-1H-1,2,3-triazol-1-yl}acetyl)azetidin-3-yl]oxy}-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-[(1-{[4-(2-hydroxyethyl)-1H-1,2,3-triazol-1-yl]acetyl}azetidin-3-yl)oxy]-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 4,4-dihydroxy-8-[(1-{[4-(2-hydroxyethyl)-1H-1,2,3-triazol-1-yl]acetyl}azetidin-3-yl)oxy]-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-[(1-{[5-(hydroxymethyl)-1H-1,2,3-triazol-1-yl]acetyl}azetidin-3-yl)oxy]-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 4,4-dihydroxy-8-[(1-{[5-(hydroxymethyl)-1H-1,2,3-triazol-1-yl]acetyl}azetidin-3-yl)oxy]-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-{[1-({5-[(methylamino)methyl]-1H-1,2,3-triazol-1-yl}acetyl)azetidin-3-yl]oxy}-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 4,4-dihydroxy-8-{[1-({5-[(methylamino)methyl]-1H-1,2,3-triazol-1-yl}acetyl)azetidin-3-yl]oxy}-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-({1-[(1H-1,2,3-triazol-4-yl)acetyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 4,4-dihydroxy-8-({1-[(1H-1,2,3-triazol-4-yl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 7-[(1-{[4-(carboxymethyl)-1H-1,2,3-triazol-1-yl]acetyl}azetidin-3-yl)oxy]-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 8-[(1-{[4-(carboxymethyl)-1H-1,2,3-triazol-1-yl]acetyl}azetidin-3-yl)oxy]-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 7-[(1-{[1-(carboxymethyl)-1H-1,2,3-triazol-4-yl]acetyl}azetidin-3-yl)oxy]-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 8-[(1-{[1-(carboxymethyl)-1H-1,2,3-triazol-4-yl]acetyl}azetidin-3-yl)oxy]-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 7-({1-[amino(1H-1,2,3-triazol-4-yl)acetyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 8-({1-[amino(1H-1,2,3-triazol-4-yl)acetyl]azetidin-3-yl}oxy-4,4-dihydroxy-5-oxa-4-boranuidiabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-({1-[(4-nitro-1H-1,2,3-triazol-1-yl)acetyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 4,4-dihydroxy-8-({1-[(4-nitro-1H-1,2,3-triazol-1-yl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 7-({1-[amino(3,4-dihydroxyphenyl)acetyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 8-({1-[amino(3,4-dihydroxyphenyl)acetyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 7-({1-[amino(2,4-dihydroxyphenyl)acetyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 8-({1-[amino(2,4-dihydroxyphenyl)acetyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 7-{[1-(S-benzyl-D-cysteinyl)azetidin-3-yl]oxy}-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid , 8-{[1-(S-benzyl-D-cysteinyl)azetidin-3-yl]oxy}-4,4-dihydroxy-5-oxa-4-boranuidiabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 7-[(1-D-cysteinylazetidin-3-yl)oxy]-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid , 7-[(1-D-cysteinylazetidin-3-yl)oxy]-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-{[1-(3-sulfanyl-D-valyl)azetidin-3-yl]oxy}-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 4,4-dihydroxy-8-{[1-(3-sulfanyl-D-valyl)azetidin-3-yl]oxy}-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 7-({1-[(2S)-2-amino-3-carboxypropanoyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 8-({1-[(2S)-2-amino-3-carboxypropanoyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 7-{[1-(D-alanyl-D-alanyl)azetidin-3-yl]oxy}-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 8-{[1-(D-alanyl-D-alanyl)azetidin-3-yl]oxy}-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 7-[(1-L-asparaginylazetidin-3-yl)oxy]-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid , 8-[(1-L-asparaginylazetidin-3-yl)oxy]-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic acid , 7-[(1-D-asparaginylazetidin-3-yl)oxy]-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid , 8-[(1-D-asparaginylazetidin-3-yl)oxy]-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 7-({1-[(2R)-2-amino-3-carboxypropanoyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid , 8-({1-[(2R)-2-amino-3-carboxypropanoyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-[(1-D-serylazetidin-3-yl)oxy]-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid , 4,4-dihydroxy-8-[(1-D-serylazetidin-3-yl)oxy]-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 7-{[1-(4-amino-4-oxobutanoyl)azetidin-3-yl]oxy}-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 8-{[1-(4-amino-4-oxobutanoyl)azetidin-3-yl]oxy}-4,4-dihydroxy-5-oxa-4-boranuidiabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 7-[(1-D-glutaminylazetidin-3-yl)oxy]-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid , 8-[(1-D-glutaminylazetidin-3-yl)oxy]-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 7-({1-[3-(carbamoylamino)-D-alanyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 8-({1-[3-(carbamoylamino)-D-alanyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 7-{[1-(3-acetamido-D-alanyl)azetidin-3-yl]oxy}-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid , 8-{[1-(3-acetamido-D-alanyl)azetidin-3-yl]oxy-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 7-{[1-(N,N-dimethyl-D-asparaginyl)azetidin-3-yl]oxy}-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid , 8-{[1-(N,N-dimethyl-D-asparaginyl)azetidin-3-yl]oxy}-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-{[1-(N-methyl-D-asparaginyl)azetidin-3-yl]oxy}-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid , 4,4-dihydroxy-8-{[1-(N-methyl-D-asparaginyl)azetidin-3-yl]oxy}-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-[(1-L-serylazetidin-3-yl)oxy]-3,4-dihydro-2H-1,2-benzoxaborine-8-carboxylic acid , 4,4-dihydroxy-8-[(1-L-serylazetidin-3-yl)oxy]-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-{[1-(4-hydroxyprolyl)azetidin-3-yl]oxy}-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid , 4,4-dihydroxy-8-{[1-(4-hydroxyprolyl)azetidin-3-yl]oxy}-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-({1-[(4R)-4-(trifluoromethyl)-D-prolyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid , 4,4-dihydroxy-8-({1-[(4R)-4-(trifluoromethyl)-D-prolyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 7-({1-[(4S)-4-fluoro-L-prolyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid , 8-({1-[(4S)-4-fluoro-L-prolyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-({1-[(pyrrolidin-3-yl)acetyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 4,4-dihydroxy-8-({1-[(pyrrolidin-3-yl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 7-[(1-{[(3R,5S)-5-(dimethylcarbamoyl)pyrrolidin-3-yl]acetyl}azetidin-3-yl)oxy]-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 8-[(1-{[(3R,5S)-5-(dimethylcarbamoyl)pyrrolidin-3-yl]acetyl}azetidin-3-yl)oxy]-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 7-[(1-{[(3S,5R)-5-(dimethylcarbamoyl)pyrrolidin-3-yl]acetyl}azetidin-3-yl)oxy]-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 8-[(1-{[(3S,5R)-5-(dimethylcarbamoyl)pyrrolidin-3-yl]acetyl}azetidin-3-yl)oxy]-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 7-[(1-{[(2R,4S)-4-fluoropyrrolidin-2-yl]acetyl}azetidin-3-yl)oxy]-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid , 8-[(1-{[(2R,4S)-4-fluoropyrrolidin-2-yl]acetyl}azetidin-3-yl)oxy]-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 7-{[1-(4,4-difluoro-L-prolyl)azetidin-3-yl]oxy}-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid , 8-{[1-(4,4-difluoro-L-prolyl)azetidin-3-yl]oxy}-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-({1-[(4R)-4-hydroxy-L-prolyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid , 4,4-dihydroxy-8-({1-[(4R)-4-hydroxy-L-prolyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-({1-[(piperidin-4-yl)acetyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 4,4-dihydroxy-8-({1-[(piperidin-4-yl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-{[1-(pyrrolidine-3-carbonyl)azetidin-3-yl]oxy}-3,4-dihydro-2H-1,2-benzoxaborimine-8-carboxylic acid , 4,4-dihydroxy-8-{[1-(pyrrolidine-3-carbonyl)azetidin-3-yl]oxy}-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-({1-[(4S)-4-hydroxy-L-prolyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid , 4,4-dihydroxy-8-({1-[(4S)-4-hydroxy-L-prolyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic acid , 7-({1-[(4S)-4-amino-L-prolyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 8-({1-[(4S)-4-amino-L-prolyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic acid , 7-({1-[(4S)-4-acetamido-L-prolyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid , 8-({1-[(4S)-4-acetamido-L-prolyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-({1-[(3R)-3-hydroxy-L-prolyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid , 4,4-dihydroxy-8-({1-[(3R)-3-hydroxy-L-prolyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic acid , 7-{[1-(4,4-dimethyl-L-prolyl)azetidin-3-yl]oxy}-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 8-{[1-(4,4-dimethyl-L-prolyl)azetidin-3-yl]oxy}-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-({1-[(pyrrolidin-2-yl)acetyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 4,4-dihydroxy-8-({1-[(pyrrolidin-2-yl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-{[1-(piperidine-2-carbonyl)azetidin-3-yl]oxy}-3,4-dihydro-2H-1,2-benzoxaborimine-8-carboxylic acid , 4,4-dihydroxy-8-{[1-(piperidine-2-carbonyl)azetidin-3-yl]oxy}-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-{[1-(piperidine-3-carbonyl)azetidin-3-yl]oxy}-3,4-dihydro-2H-1,2-benzoxaborimine-8-carboxylic acid , 4,4-dihydroxy-8-{[1-(piperidine-3-carbonyl)azetidin-3-yl]oxy}-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-{[1-(piperidine-4-carbonyl)azetidin-3-yl]oxy}-3,4-dihydro-2H-1,2-benzoxaborimine-8-carboxylic acid , 4,4-dihydroxy-8-{[1-(piperidine-4-carbonyl)azetidin-3-yl]oxy}-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-({1-[(2S)-oxolane-2-carbonyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 4,4-dihydroxy-8-({1-[(2S)-oxolane-2-carbonyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-({1-[(4R)-4-phenyl-L-prolyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid , 4,4-dihydroxy-8-({1-[(4R)-4-phenyl-L-prolyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 7-({1-[(1S,3S,5S)-2-azabicyclo[3.1.0]hexane-3-carbonyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 8-({1-[(1S,3S,5S)-2-azabicyclo[3.1.0]hexane-3-carbonyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidiabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-{[1-(1-methyl-L-prolyl)azetidin-3-yl]oxy}-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid , 4,4-dihydroxy-8-{[1-(1-methyl-L-prolyl)azetidin-3-yl]oxy}-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-({1-[(piperidin-3-yl)acetyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborimine-8-carboxylic acid , 4,4-dihydroxy-8-({1-[(piperidin-3-yl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-({1-[(morpholin-2-yl)acetyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborimine-8-carboxylic acid , 4,4-dihydroxy-8-({1-[(morpholin-2-yl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 7-({1-[(azetidin-3-yl)acetyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborimine-8-carboxylic acid , 8-({1-[(azetidin-3-yl)acetyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 7-({1-[amino(pyrrolidin-3-yl)acetyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 8-({1-[amino(pyrrolidin-3-yl)acetyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-({1-[3-(pyrrolidin-2-yl)propanoyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 4,4-dihydroxy-8-({1-[3-(pyrrolidin-2-yl)propanoyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 7-({1-[(4R)-4-amino-L-prolyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid , 8-({1-[(4R)-4-amino-L-prolyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic acid , 7-({1-[(4R)-4-acetamido-L-prolyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid , 8-({1-[(4R)-4-acetamido-L-prolyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic acid , 7-({1-[amino(piperidin-4-yl)acetyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 8-({1-[amino(piperidin-4-yl)acetyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-({1-[(piperidin-2-yl)acetyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 4,4-dihydroxy-8-({1-[(piperidin-2-yl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 7-({1-[(4S)-4-carbamoyl-L-prolyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 8-({1-[(4S)-4-carbamoyl-L-prolyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-[(1-{[(3R)-pyrrolidin-3-yl]acetyl}azetidin-3-yl)oxy]-3,4-dihydro-2H-1,2-benzoxaborine-8-carboxylic acid , 4,4-dihydroxy-8-[(1-{[(3R)-pyrrolidin-3-yl]acetyl}azetidin-3-yl)oxy]-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-[(1-{[(3S)-pyrrolidin-3-yl]acetyl}azetidin-3-yl)oxy]-3,4-dihydro-2H-1,2-benzoxaborine-8-carboxylic acid , 4,4-dihydroxy-8-[(1-{[(3S)-pyrrolidin-3-yl]acetyl}azetidin-3-yl)oxy]-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-[(1-{[(2R)-pyrrolidin-2-yl]acetyl}azetidin-3-yl)oxy]-3,4-dihydro-2H-1,2-benzoxaborine-8-carboxylic acid , 4,4-dihydroxy-8-[(1-{[(2R)-pyrrolidin-2-yl]acetyl}azetidin-3-yl)oxy]-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-[(1-{[(2S)-pyrrolidin-2-yl]acetyl}azetidin-3-yl)oxy]-3,4-dihydro-2H-1,2-benzoxaborine-8-carboxylic acid , 4,4-dihydroxy-8-[(1-{[(2S)-pyrrolidin-2-yl]acetyl}azetidin-3-yl)oxy]-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-({1-[(piperazin-2-yl)acetyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 4,4-dihydroxy-8-({1-[(piperazin-2-yl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 7-({1-[(1,1-dioxo-1λ ６ -thiomorpholin-2-yl)acetyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborimine-8-carboxylic acid , 8-({1-[(1,1-dioxo-1λ ６ -thiomorpholin-2-yl)acetyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 7-({1-[(2S)-4-acetamido-2-aminobutanoyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 8-({1-[(2S)-4-acetamido-2-aminobutanoyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 7-{[1-(L-α-asparaginyl)azetidin-3-yl]oxy}-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid , 8-{[1-(L-α-asparaginyl)azetidin-3-yl]oxy}-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 7-{[1-(L-alanyl-L-alanyl)azetidin-3-yl]oxy}-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid , 8-{[1-(L-alanyl-L-alanyl)azetidin-3-yl]oxy}-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 7-{[1-(glycyl-D-alanyl)azetidin-3-yl]oxy}-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid , 8-{[1-(glycyl-D-alanyl)azetidin-3-yl]oxy}-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , N-[(2R)-1-{3-[(8-carboxy-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinin-7-yl)oxy]azetidin-1-yl}-1-oxopropan-2-yl]-D-α-asparagine , N-[(2R)-1-{3-[(7-carboxy-4,4-hydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-trien-8-yl)oxy]azetidin-1-yl}-1-oxopropan-2-yl]-D-α-asparagine , N １ -[(2R)-1-{3-[(8-carboxy-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinin-7-yl)oxy]azetidin-1-yl}-1-oxopropan-2-yl]-D-aspartamide , N １-[(2R)-1-{3-[(7-carboxy-4,4-hydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-trien-8-yl)oxy]azetidin-1-yl}-1-oxopropan-2-yl]-D-aspartamide , N-[(2R)-1-{3-[(8-carboxy-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinin-7-yl)oxy]azetidin-1-yl}-1-oxopropan-2-yl]-D-serinamide , N-[(2R)-1-{3-[(7-carboxy-4,4-hydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-trien-8-yl)oxy]azetidin-1-yl}-1-oxopropan-2-yl]-D-serinamide , 7-({1-[(3S)-3-amino-3-carboxypropanoyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid , 8-({1-[(3S)-3-amino-3-carboxypropanoyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-({1-[(1H-imidazol-4-yl)(methylamino)acetyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborimine-8-carboxylic acid , 4,4-dihydroxy-8-({1-[(1H-imidazol-4-yl)(methylamino)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidiabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-({1-[(1H-imidazol-4-yl)(methylamino)acetyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborimine-8-carboxylic acid , 4,4-dihydroxy-8-({1-[(1H-imidazol-4-yl)(methylamino)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidiabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-{[1-(2-methyl-D-seryl)azetidin-3-yl]oxy}-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid , 4,4-dihydroxy-8-{[1-(2-methyl-D-seryl)azetidin-3-yl]oxy}-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-{[1-(2-methyl-L-seryl)azetidin-3-yl]oxy}-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid , 4,4-dihydroxy-8-{[1-(2-methyl-L-seryl)azetidin-3-yl]oxy}-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-({1-[(3-oxopiperazin-2-yl)acetyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 4,4-dihydroxy-8-({1-[(3-oxopiperazin-2-yl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 7-({1-[(3S)-3-amino-5-carboxypentanoyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 8-({1-[(3S)-3-amino-5-carboxypentanoyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 7-({1-[(3R)-3-amino-3-carboxypropanoyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 8-({1-[(3R)-3-amino-3-carboxypropanoyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 7-({1-[(4R)-4-amino-4-carboxybutanoyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 8-({1-[(3R)-3-amino-3-carboxypropanoyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 7-({1-[(3S)-3,6-diamino-6-oxohexanoyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 8-({1-[(3S)-3,6-diamino-6-oxohexanoyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 7-{[1-(D-α-asparaginyl)azetidin-3-yl]oxy}-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid , 8-{[1-(D-α-asparaginyl)azetidin-3-yl]oxy}-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 7-{[1-(D-α-glutaminyl)azetidin-3-yl]oxy}-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid , 8-{[1-(D-α-glutaminyl)azetidin-3-yl]oxy}-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 7-({1-[(4S)-4-amino-4-carboxybutanoyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 8-({1-[(4S)-4-amino-4-carboxybutanoyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 7-{[1-(L-α-glutaminyl)azetidin-3-yl]oxy}-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid , 8-{[1-(L-α-glutaminyl)azetidin-3-yl]oxy}-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-[(1-D-threonylazetidin-3-yl)oxy]-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid , 4,4-dihydroxy-8-[(1-D-threonylazetidin-3-yl)oxy]-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid , 2-hydroxy-7-[(1-L-threonylazetidin-3-yl)oxy]-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid , and 4,4-dihydroxy-8-[(1-L-threonylazetidin-3-yl)oxy]-5-oxa-4-boranuidabicyclo[4.4.0]deca-1(6),7,9-triene-7-carboxylic acid [Item 55] The following formula (11): [In formula (11), R Ｇ is a hydroxyl group, a thiol group, or -NHRａ１ and R ａ１ , Z, L １ , L ２ , X, R １ , R ２ , R ３ , and R ４ has the same definition as in item 1, and formula (1a) has the same definition as in item 1. [Item 56] A compound represented by the formula (11) or a pharmaceutically acceptable salt thereof: [In formula (12), X, R １ , R ２ , R ３ , and R ４ [Item 57] The compound according to item 55, or a pharmaceutically acceptable salt thereof, wherein the compound of formula (12) is represented by the following formula (13): [In formula (13), X, Y, ring A, L ３ , L ４ , R １ , R ２ , R ４ , and R ５ [Item 58] The compound according to item 55 or 56, or a pharmaceutically acceptable salt thereof, wherein X and R are as defined in any one of the preceding items. Ｇ is a hydroxyl group, and R ４ [Item 59] The compound according to any one of Items 55 to 57, wherein R represents a carboxyl group, and Ring A represents an optionally substituted 4- to 6-membered nitrogen-containing non-aryl heterocycle, or a pharmaceutically acceptable salt thereof. [Item 59] The compound of Formula (13) or a pharmaceutically acceptable salt thereof, wherein R represents a carboxyl group, and Ring A represents an optionally substituted 4- to 6-membered nitrogen-containing non-aryl heterocycle. [In formula (14), X, L ３ , L ４ , m, n, and R ５ [Item 60] The compound according to any one of Items 55 to 58, wherein R is as defined in any one of the preceding items, or a pharmaceutically acceptable salt thereof. Ｇ [Item 61] The compound according to any one of Items 55 to 59, or a pharmaceutically acceptable salt thereof, wherein R is a hydroxyl group or a thiol group. Ｇ[Item 62] The compound or a pharmaceutically acceptable salt thereof according to any one of Items 55 to 60, wherein X is a hydroxyl group or C １－６ [Item 63] The compound according to any one of items 55 to 62, or a pharmaceutically acceptable salt thereof, wherein X is an alkoxy group. [Item 64] The compound according to any one of items 55 to 63, or a pharmaceutically acceptable salt thereof, wherein m is 1 or 2, n is 1 or 2, and m+n is 2 or 3. [Item 65] The compound according to any one of items 55 to 64, or a pharmaceutically acceptable salt thereof, wherein m is 1 and n is 1. [Item 66] L ３ [Item 67] The compound according to any one of Items 55 to 65, or a pharmaceutically acceptable salt thereof, wherein L is as defined in any one of the preceding items. ４ and R ５ [Item 68] The compound according to any one of Items 55 to 66, or a pharmaceutically acceptable salt thereof, wherein R is as defined in any one of the preceding items. [Item 69] The compound according to Item 55, or a pharmaceutically acceptable salt thereof, selected from the group consisting of the following compounds: 6-[(1-acetylazetidin-3-yl)oxy]-3-(2-boronoethyl)-2-hydroxybenzoic acid , 3-(2-boronoethyl)-2-hydroxy-6-({1-[(1H-imidazol-5-yl)acetyl]azetidin-3-yl}oxy)benzoic acid , 3-(2-boronoethyl)-2-hydroxy-6-{[1-(methanesulfonyl)azetidin-3-yl]oxy}benzoic acid , 6-({1-[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]azetidin-3-yl}oxy)-3-(2-boronoethyl)-2-hydroxybenzoic acid , 6-({1-[(2-amino-1,3-thiazol-4-yl)(methoxyimino)acetyl]azetidin-3-yl}oxy)-3-(2-boronoethyl)-2-hydroxybenzoic acid , 3-(2-boronoethyl)-2-hydroxy-6-{[1-(pyridine-2-carbonyl)azetidin-3-yl]oxy}benzoic acid , 3-(2-boronoethyl)-2-hydroxy-6-({1-[(methylsulfanyl)acetyl]azetidin-3-yl}oxy)benzoic acid , 3-(2-boronoethyl)-2-hydroxy-6-{[1-(1H-1,2,4-triazole-3-carbonyl)azetidin-3-yl]oxy}benzoic acid , 3-(2-boronoethyl)-2-hydroxy-6-{[1-(1-oxido-2-pyridinylcarbonyl)azetidin-3-yl]oxy}benzoic acid , 6-({1-[(2R)-2-amino-2-phenylacetyl]azetidin-3-yl}oxy)-3-(2-boronoethyl)-2-hydroxybenzoic acid , 6-[(1-benzoylazetidin-3-yl)oxy]-3-(2-boronoethyl)-2-hydroxybenzoic acid , 3-(2-boronoethyl)-2-hydroxy-6-{[1-(pyridine-3-carbonyl)azetidin-3-yl]oxy}benzoic acid , 3-(2-boronoethyl)-2-hydroxy-6-({1-[(pyridin-2-yl)acetyl]azetidin-3-yl}oxy)benzoic acid , 3-(2-boronoethyl)-2-hydroxy-6-({1-[(pyridin-3-yl)acetyl]azetidin-3-yl}oxy)benzoic acid , 6-({1-[(2S)-2-amino-2-phenylacetyl]azetidin-3-yl}oxy)-3-(2-boronoethyl)-2-hydroxybenzoic acid , 3-(2-boronoethyl)-2-hydroxy-6-({1-[(pyridin-4-yl)acetyl]azetidin-3-yl}oxy)benzoic acid , 3-(2-boronoethyl)-2-hydroxy-6-({1-[(4-hydroxyphenyl)acetyl]azetidin-3-yl}oxy)benzoic acid , 3-(2-boronoethyl)-2-hydroxy-6-({1-[(1H-1,2,4-triazol-1-yl)acetyl]azetidin-3-yl}oxy)benzoic acid , 6-({1-[amino(1H-imidazol-5-yl)acetyl]azetidin-3-yl}oxy)-3-(2-boronoethyl)-2-hydroxybenzoic acid , 3-(2-boronoethyl)-2-hydroxy-6-{[1-(phenylacetyl)azetidin-3-yl]oxy}benzoic acid , 3-(2-boronoethyl)-2-hydroxy-6-{[1-(3-phenylpropanoyl)azetidin-3-yl]oxy}benzoic acid , 3-(2-boronoethyl)-2-hydroxy-6-({1-[(1H-imidazol-1-yl)acetyl]azetidin-3-yl}oxy)benzoic acid , 3-(2-boronoethyl)-2-hydroxy-6-({1-[(1H-tetrazol-1-yl)acetyl]azetidin-3-yl}oxy)benzoic acid , 3-(2-boronoethyl)-2-hydroxy-6-({1-[(2H-tetrazol-5-yl)acetyl]azetidin-3-yl}oxy)benzoic acid , 3-(2-boronoethyl)-2-hydroxy-6-[(1-D-phenylalanylazetidin-3-yl)oxy]benzoic acid , 3-(2-boronoethyl)-2-hydroxy-6-[(1-D-tyrosylazetidin-3-yl)oxy]benzoic acid , 3-(2-boronoethyl)-6-[(1-D-histidylazetidin-3-yl)oxy]-2-hydroxybenzoic acid , 3-(2-boronoethyl)-2-hydroxy-6-[(1-D-valylazetidin-3-yl)oxy]benzoic acid , 3-(2-boronoethyl)-6-[(1-L-histidylazetidin-3-yl)oxy]-2-hydroxybenzoic acid , 3-(2-boronoethyl)-6-[(1-{(2R)-2-[(4-ethyl-2,3-dioxopiperazine-1-carbonyl)amino]-2-phenylacetyl}azetidin-3-yl)oxy]-2-hydroxybenzoic acid , 3-(2-boronoethyl)-2-hydroxy-6-[(1-D-prolylazetidin-3-yl)oxy]benzoic acid , 3-(2-boronoethyl)-2-hydroxy-6-[(1-L-prolylazetidin-3-yl)oxy]benzoic acid , 6-[(1-{[4-(2-aminoethyl)-1H-imidazol-1-yl]acetyl}azetidin-3-yl)oxy]-3-(2-boronoethyl)-2-hydroxybenzoic acid , 3-(2-boronoethyl)-6-{[1-(3,4-dihydroxybenzoyl)azetidin-3-yl]oxy}-2-hydroxybenzoic acid , and 3-(2-boronoethyl)-2-hydroxy-6-{[1-(hydroxycarbamoyl)azetidin-3-yl]oxy}benzoic acid [Item 69] The compound according to Item 55, or a pharmaceutically acceptable salt thereof, selected from the group consisting of the following compounds: 6-({1-[(2R)-2-amino-2-(1H-imidazol-4-yl)acetyl]azetidin-3-yl}oxy)-3-(2-boronoethyl)-2-hydroxybenzoic acid , 6-({1-[(2S)-2-amino-2-(1H-imidazol-4-yl)acetyl]azetidin-3-yl}oxy)-3-(2-boronoethyl)-2-hydroxybenzoic acid , 6-({1-[amino(1-methyl-1H-imidazol-4-yl)acetyl]azetidin-3-yl}oxy)-3-(2-boronoethyl)-2-hydroxybenzoic acid , 3-(2-boronoethyl)-2-hydroxy-6-{[1-(4H-1,2,4-triazole-3-sulfonyl)azetidin-3-yl]oxy}benzoic acid , 6-({1-[2-amino-2-(1H-imidazol-4-yl)( ２H) Ethanoyl]azetidin-3-yl}oxy)-3-(2-boronoethyl)-2-hydroxybenzoic acid , 6-({1-[2-amino-2-(1H-imidazol-4-yl)propanoyl]azetidin-3-yl}oxy)-3-(2-boronoethyl)-2-hydroxybenzoic acid , 6-({(3S)-1-[amino(1H-imidazol-4-yl)acetyl]pyrrolidin-3-yl}oxy)-3-(2-boronoethyl)-2-hydroxybenzoic acid , 3-(2-boronoethyl)-2-hydroxy-6-{[1-(4-hydroxy-6-methylpyridine-3-carbonyl)azetidin-3-yl]oxy}benzoic acid , 6-({1-[amino(1-methyl-1H-imidazol-5-yl)acetyl]azetidin-3-yl}oxy)-3-(2-boronoethyl)-2-hydroxybenzoic acid , 6-[(1-{amino[1-(carboxymethyl)-1H-imidazol-4-yl]acetyl}azetidin-3-yl)oxy]-3-(2-boronoethyl)-2-hydroxybenzoic acid , 6-[(1-{amino[1-(2-amino-2-oxoethyl)-1H-imidazol-4-yl]acetyl}azetidin-3-yl)oxy]-3-(2-boronoethyl)-2-hydroxybenzoic acid , 6-({1-[amino(pyridin-3-yl)acetyl]azetidin-3-yl}oxy)-3-(2-boronoethyl)-2-hydroxybenzoic acid , 6-({1-[amino(1-methyl-1H-pyrazol-4-yl)acetyl]azetidin-3-yl}oxy)-3-(2-boronoethyl)-2-hydroxybenzoic acid , 6-({(3R)-1-[amino(1H-imidazol-4-yl)acetyl]pyrrolidin-3-yl}oxy)-3-(2-boronoethyl)-2-hydroxybenzoic acid , 6-({1-[amino(2-methyl-1H-imidazol-4-yl)acetyl]azetidin-3-yl}oxy)-3-(2-boronoethyl)-2-hydroxybenzoic acid , 6-({1-[amino(1,3-thiazol-4-yl)acetyl]azetidin-3-yl}oxy)-3-(2-boronoethyl)-2-hydroxybenzoic acid , 3-(2-boronoethyl)-2-hydroxy-6-{[1-(1H-imidazole-4-sulfonyl)azetidin-3-yl]oxy}benzoic acid , 3-(2-boronoethyl)-2-hydroxy-6-{[1-(pyridine-3-sulfonyl)azetidin-3-yl]oxy}benzoic acid , 3-(2-boronoethyl)-2-hydroxy-6-{[1-(1-oxo-1λ ５ -pyridine-2-sulfonyl)azetidin-3-yl]oxy}benzoic acid , 6-({1-[(2-amino-1,3-thiazol-4-yl)acetyl]azetidin-3-yl}oxy)-3-(2-boronoethyl)-2-hydroxybenzoic acid , 6-{[1-(2-amino-1,3-thiazole-4-carbonyl)azetidin-3-yl]oxy}-3-(2-boronoethyl)-2-hydroxybenzoic acid , 3-(2-boronoethyl)-2-hydroxy-6-({1-[(1H-1,2,3-triazol-1-yl)acetyl]azetidin-3-yl}oxy)benzoic acid , 6-[(1-{[1-(2-aminoethyl)-1H-imidazol-4-yl]acetyl}azetidin-3-yl)oxy]-3-(2-boronoethyl)-2-hydroxybenzoic acid , 3-(2-boronoethyl)-2-hydroxy-6-{[1-(1H-imidazole-4-carbonyl)azetidin-3-yl]oxy}benzoic acid , 3-(2-boronoethyl)-2-hydroxy-6-{[1-(1H-imidazole-2-carbonyl)azetidin-3-yl]oxy}benzoic acid , 3-(2-boronoethyl)-2-hydroxy-6-[(1-{[4-(hydroxymethyl)-1H-1,2,3-triazol-1-yl]acetyl}azetidin-3-yl)oxy]benzoic acid , 3-(2-boronoethyl)-2-hydroxy-6-{[1-({4-[(methylamino)methyl]-1H-1,2,3-triazol-1-yl}acetyl)azetidin-3-yl]oxy}benzoic acid , 3-(2-boronoethyl)-2-hydroxy-6-{[1-({4-[(piperazin-1-yl)methyl]-1H-1,2,3-triazol-1-yl}acetyl)azetidin-3-yl]oxy}benzoic acid , 3-(2-boronoethyl)-2-hydroxy-6-[(1-{[4-(2-hydroxyethyl)-1H-1,2,3-triazol-1-yl]acetyl}azetidin-3-yl)oxy]benzoic acid , 3-(2-boronoethyl)-2-hydroxy-6-[(1-{[5-(hydroxymethyl)-1H-1,2,3-triazol-1-yl]acetyl}azetidin-3-yl)oxy]benzoic acid , 3-(2-boronoethyl)-2-hydroxy-6-{[1-({5-[(methylamino)methyl]-1H-1,2,3-triazol-1-yl}acetyl)azetidin-3-yl]oxy}benzoic acid , 3-(2-boronoethyl)-2-hydroxy-6-({1-[(1H-1,2,3-triazol-4-yl)acetyl]azetidin-3-yl}oxy)benzoic acid , 3-(2-boronoethyl)-6-[(1-{[4-(carboxymethyl)-1H-1,2,3-triazol-1-yl]acetyl}azetidin-3-yl)oxy]-2-hydroxybenzoic acid , 3-(2-boronoethyl)-6-[(1-{[1-(carboxymethyl)-1H-1,2,3-triazol-4-yl]acetyl}azetidin-3-yl)oxy]-2-hydroxybenzoic acid , 6-({1-[amino(1H-1,2,3-triazol-4-yl)acetyl]azetidin-3-yl}oxy)-3-(2-boronoethyl)-2-hydroxybenzoic acid , 3-(2-boronoethyl)-2-hydroxy-6-({1-[(4-nitro-1H-1,2,3-triazol-1-yl)acetyl]azetidin-3-yl}oxy)benzoic acid , 6-({1-[amino(3,4-dihydroxyphenyl)acetyl]azetidin-3-yl}oxy)-3-(2-boronoethyl)-2-hydroxybenzoic acid , 6-({1-[amino(2,4-dihydroxyphenyl)acetyl]azetidin-3-yl}oxy)-3-(2-boronoethyl)-2-hydroxybenzoic acid , 6-{[1-(S-benzyl-D-cysteinyl)azetidin-3-yl]oxy}-3-(2-boronoethyl)-2-hydroxybenzoic acid , 3-(2-boronoethyl)-6-[(1-D-cysteinylazetidin-3-yl)oxy]-2-hydroxybenzoic acid , 3-(2-boronoethyl)-2-hydroxy-6-{[1-(3-sulfanyl-D-valyl)azetidin-3-yl]oxy}benzoic acid , 6-({1-[(2S)-2-amino-3-carboxypropanoyl]azetidin-3-yl}oxy)-3-(2-boronoethyl)-2-hydroxybenzoic acid , 6-{[1-(D-alanyl-D-alanyl)azetidin-3-yl]oxy}-3-(2-boronoethyl)-2-hydroxybenzoic acid , 6-[(1-L-asparaginylazetidin-3-yl)oxy]-3-(2-boronoethyl)-2-hydroxybenzoic acid , 6-[(1-D-asparaginylazetidin-3-yl)oxy]-3-(2-boronoethyl)-2-hydroxybenzoic acid , 6-({1-[(2R)-2-amino-3-carboxypropanoyl]azetidin-3-yl}oxy)-3-(2-boronoethyl)-2-hydroxybenzoic acid , 3-(2-boronoethyl)-2-hydroxy-6-[(1-D-serylazetidin-3-yl)oxy]benzoic acid , 6-{[1-(4-amino-4-oxobutanoyl)azetidin-3-yl]oxy}-3-(2-boronoethyl)-2-hydroxybenzoic acid , 3-(2-boronoethyl)-6-[(1-D-glutaminylazetidin-3-yl)oxy]-2-hydroxybenzoic acid , 3-(2-boronoethyl)-6-({1-[3-(carbamoylamino)-D-alanyl]azetidin-3-yl}oxy)-2-hydroxybenzoic acid , 6-{[1-(3-acetamido-D-alanyl)azetidin-3-yl]oxy}-3-(2-boronoethyl)-2-hydroxybenzoic acid , 3-(2-boronoethyl)-6-{[1-(N,N-dimethyl-D-asparaginyl)azetidin-3-yl]oxy}-2-hydroxybenzoic acid , 3-(2-boronoethyl)-2-hydroxy-6-{[1-(N-methyl-D-asparaginyl)azetidin-3-yl]oxy}benzoic acid , 3-(2-boronoethyl)-2-hydroxy-6-[(1-L-serylazetidin-3-yl)oxy]benzoic acid , 3-(2-boronoethyl)-2-hydroxy-6-{[1-(4-hydroxyprolyl)azetidin-3-yl]oxy}benzoic acid , 3-(2-boronoethyl)-2-hydroxy-6-({1-[(4R)-4-(trifluoromethyl)-D-prolyl]azetidin-3-yl}oxy)benzoic acid , 3-(2-boronoethyl)-6-({1-[(4S)-4-fluoro-L-prolyl]azetidin-3-yl}oxy)-2-hydroxybenzoic acid , 3-(2-boronoethyl)-2-hydroxy-6-({1-[(pyrrolidin-3-yl)acetyl]azetidin-3-yl}oxy)benzoic acid , 3-(2-boronoethyl)-6-[(1-{[(3R,5S)-5-(dimethylcarbamoyl)pyrrolidin-3-yl]acetyl}azetidin-3-yl)oxy]-2-hydroxybenzoic acid , 3-(2-boronoethyl)-6-[(1-{[(3S,5R)-5-(dimethylcarbamoyl)pyrrolidin-3-yl]acetyl}azetidin-3-yl)oxy]-2-hydroxybenzoic acid , 3-(2-boronoethyl)-6-[(1-{[(2R,4S)-4-fluoropyrrolidin-2-yl]acetyl}azetidin-3-yl)oxy]-2-hydroxybenzoic acid , 3-(2-boronoethyl)-6-{[1-(4,4-difluoro-L-prolyl)azetidin-3-yl]oxy}-2-hydroxybenzoic acid , 3-(2-boronoethyl)-2-hydroxy-6-({1-[(4R)-4-hydroxy-L-prolyl]azetidin-3-yl}oxy)benzoic acid , 3-(2-boronoethyl)-2-hydroxy-6-({1-[(piperidin-4-yl)acetyl]azetidin-3-yl}oxy)benzoic acid , 3-(2-boronoethyl)-2-hydroxy-6-{[1-(pyrrolidine-3-carbonyl)azetidin-3-yl]oxy}benzoic acid , 3-(2-boronoethyl)-2-hydroxy-6-({1-[(4S)-4-hydroxy-L-prolyl]azetidin-3-yl}oxy)benzoic acid , 6-({1-[(4S)-4-amino-L-prolyl]azetidin-3-yl}oxy)-3-(2-boronoethyl)-2-hydroxybenzoic acid , 6-({1-[(4S)-4-acetamido-L-prolyl]azetidin-3-yl}oxy)-3-(2-boronoethyl)-2-hydroxybenzoic acid , 3-(2-boronoethyl)-2-hydroxy-6-({1-[(3R)-3-hydroxy-L-prolyl]azetidin-3-yl}oxy)benzoic acid , 3-(2-boronoethyl)-6-{[1-(4,4-dimethyl-L-prolyl)azetidin-3-yl]oxy}-2-hydroxybenzoic acid , 3-(2-boronoethyl)-2-hydroxy-6-({1-[(pyrrolidin-2-yl)acetyl]azetidin-3-yl}oxy)benzoic acid , 3-(2-boronoethyl)-2-hydroxy-6-{[1-(piperidine-2-carbonyl)azetidin-3-yl]oxy}benzoic acid , 3-(2-boronoethyl)-2-hydroxy-6-{[1-(piperidine-3-carbonyl)azetidin-3-yl]oxy}benzoic acid , 3-(2-boronoethyl)-2-hydroxy-6-{[1-(piperidine-4-carbonyl)azetidin-3-yl]oxy}benzoic acid , 3-(2-boronoethyl)-2-hydroxy-6-({1-[(2S)-oxolane-2-carbonyl]azetidin-3-yl}oxy)benzoic acid , 3-(2-boronoethyl)-2-hydroxy-6-({1-[(4R)-4-phenyl-L-prolyl]azetidin-3-yl}oxy)benzoic acid , 6-({1-[(1S,3S,5S)-2-azabicyclo[3.1.0]hexane-3-carbonyl]azetidin-3-yl}oxy)-3-(2-boronoethyl)-2-hydroxybenzoic acid , 3-(2-boronoethyl)-2-hydroxy-6-{[1-(1-methyl-L-prolyl)azetidin-3-yl]oxy}benzoic acid , 3-(2-boronoethyl)-2-hydroxy-6-({1-[(piperidin-3-yl)acetyl]azetidin-3-yl}oxy)benzoic acid , 3-(2-boronoethyl)-2-hydroxy-6-({1-[(morpholin-2-yl)acetyl]azetidin-3-yl}oxy)benzoic acid , 6-({1-[(azetidin-3-yl)acetyl]azetidin-3-yl}oxy)-3-(2-boronoethyl)-2-hydroxybenzoic acid , 6-({1-[amino(pyrrolidin-3-yl)acetyl]azetidin-3-yl}oxy)-3-(2-boronoethyl)-2-hydroxybenzoic acid , 3-(2-boronoethyl)-2-hydroxy-6-({1-[3-(pyrrolidin-2-yl)propanoyl]azetidin-3-yl}oxy)benzoic acid , 6-({1-[(4R)-4-amino-L-prolyl]azetidin-3-yl}oxy)-3-(2-boronoethyl)-2-hydroxybenzoic acid , 6-({1-[(4R)-4-acetamido-L-prolyl]azetidin-3-yl}oxy)-3-(2-boronoethyl)-2-hydroxybenzoic acid , 6-({1-[amino(piperidin-4-yl)acetyl]azetidin-3-yl}oxy)-3-(2-boronoethyl)-2-hydroxybenzoic acid , 3-(2-boronoethyl)-2-hydroxy-6-({1-[(piperidin-2-yl)acetyl]azetidin-3-yl}oxy)benzoic acid , 3-(2-boronoethyl)-6-({1-[(4S)-4-carbamoyl-L-prolyl]azetidin-3-yl}oxy)-2-hydroxybenzoic acid , 3-(2-boronoethyl)-2-hydroxy-6-[(1-{[(3R)-pyrrolidin-3-yl]acetyl}azetidin-3-yl)oxy]benzoic acid , 3-(2-boronoethyl)-2-hydroxy-6-[(1-{[(3S)-pyrrolidin-3-yl]acetyl}azetidin-3-yl)oxy]benzoic acid , 3-(2-boronoethyl)-2-hydroxy-6-[(1-{[(2R)-pyrrolidin-2-yl]acetyl}azetidin-3-yl)oxy]benzoic acid , 3-(2-boronoethyl)-2-hydroxy-6-[(1-{[(2S)-pyrrolidin-2-yl]acetyl}azetidin-3-yl)oxy]benzoic acid , 3-(2-boronoethyl)-2-hydroxy-6-({1-[(piperazin-2-yl)acetyl]azetidin-3-yl}oxy)benzoic acid , 3-(2-boronoethyl)-6-({1-[(1,1-dioxo-1λ ６ -thiomorpholin-2-yl)acetyl]azetidin-3-yl}oxy)-2-hydroxybenzoic acid , 6-({1-[(2S)-4-acetamido-2-aminobutanoyl]azetidin-3-yl}oxy)-3-(2-boronoethyl)-2-hydroxybenzoic acid , 6-{[1-(L-α-asparaginyl)azetidin-3-yl]oxy}-3-(2-boronoethyl)-2-hydroxybenzoic acid , 6-{[1-(L-alanyl-L-alanyl)azetidin-3-yl]oxy}-3-(2-boronoethyl)-2-hydroxybenzoic acid , 3-(2-boronoethyl)-6-{[1-(glycyl-D-alanyl)azetidin-3-yl]oxy}-2-hydroxybenzoic acid , N-[(2R)-1-{3-[4-(2-boronoethyl)-2-carboxy-3-hydroxyphenoxy]azetidin-1-yl}-1-oxopropan-2-yl]-D-α-asparagine , N １ -[(2R)-1-{3-[4-(2-boronoethyl)-2-carboxy-3-hydroxyphenoxy]azetidin-1-yl}-1-oxopropan-2-yl]-D-aspartamide , N-[(2R)-1-{3-[4-(2-boronoethyl)-2-carboxy-3-hydroxyphenoxy]azetidin-1-yl}-1-oxopropan-2-yl]-D-serinamide , 6-({1-[(3S)-3-amino-3-carboxypropanoyl]azetidin-3-yl}oxy)-3-(2-boronoethyl)-2-hydroxybenzoic acid , 3-(2-boronoethyl)-2-hydroxy-6-({1-[(1H-imidazol-4-yl)(methylamino)acetyl]azetidin-3-yl}oxy)benzoic acid , 3-(2-boronoethyl)-6-({1-[(dimethylamino)(1H-imidazol-4-yl)acetyl]azetidin-3-yl}oxy)-2-hydroxybenzoic acid , 3-(2-boronoethyl)-2-hydroxy-6-{[1-(2-methyl-D-seryl)azetidin-3-yl]oxy}benzoic acid , 3-(2-boronoethyl)-2-hydroxy-6-{[1-(2-methyl-L-seryl)azetidin-3-yl]oxy}benzoic acid , 3-(2-boronoethyl)-2-hydroxy-6-({1-[(3-oxopiperazin-2-yl)acetyl]azetidin-3-yl}oxy)benzoic acid , 6-({1-[(3S)-3-amino-5-carboxypentanoyl]azetidin-3-yl}oxy)-3-(2-boronoethyl)-2-hydroxybenzoic acid , 6-({1-[(3R)-3-amino-3-carboxypropanoyl]azetidin-3-yl}oxy)-3-(2-boronoethyl)-2-hydroxybenzoic acid , 6-({1-[(4R)-4-amino-4-carboxybutanoyl]azetidin-3-yl}oxy)-3-(2-boronoethyl)-2-hydroxybenzoic acid , 3-(2-boronoethyl)-6-({1-[(3S)-3,6-diamino-6-oxohexanoyl]azetidin-3-yl}oxy)-2-hydroxybenzoic acid , 6-{[1-(D-α-asparaginyl)azetidin-3-yl]oxy}-3-(2-boronoethyl)-2-hydroxybenzoic acid , 3-(2-boronoethyl)-6-{[1-(D-α-glutaminyl)azetidin-3-yl]oxy}-2-hydroxybenzoic acid , 6-({1-[(4S)-4-amino-4-carboxybutanoyl]azetidin-3-yl}oxy)-3-(2-boronoethyl)-2-hydroxybenzoic acid , 3-(2-boronoethyl)-6-{[1-(L-α-glutaminyl)azetidin-3-yl]oxy}-2-hydroxybenzoic acid , 3-(2-boronoethyl)-2-hydroxy-6-[(1-D-threonylazetidin-3-yl)oxy]benzoic acid , and 3-(2-boronoethyl)-2-hydroxy-6-[(1-L-threonylazetidin-3-yl)oxy]benzoic acid [Item 70] A pharmaceutical comprising the compound according to any one of Items 1 to 69 or a pharmaceutically acceptable salt thereof. [Item 71] The pharmaceutical according to Item 70, which is a therapeutic or preventive agent for bacterial infections. [Item 72] A β-lactamase inhibitor comprising the compound according to any one of Items 1 to 69 or a pharmaceutically acceptable salt thereof as an active ingredient. [Item 73] A pharmaceutical composition comprising the compound according to any one of Items 1 to 69 or a pharmaceutically acceptable salt thereof and a pharmaceutically acceptable carrier. [Item 74] The pharmaceutical composition according to Item 73, further comprising an additional drug. [Item 75] The pharmaceutical composition according to Item 74, wherein the additional drug is selected from the group consisting of antibacterial agents, antifungal agents, antiviral agents, anti-inflammatory agents and antiallergic agents. [Item 76] The pharmaceutical composition according to Item 74 or 75, wherein the additional drug is a β-lactam drug.[Item 77] The beta-lactam drug as an additional drug is amoxicillin, ampicillin (pivampicillin, hetacillin, bacampicillin, metampicillin, talampicillin), epicillin, carbenicillin (carindacillin), ticarcillin, temocillin, azlocillin, piperacillin, mezlocillin, mecillinam (pivmecillinam), sulbenicillin, benzylpenicillin (G), clometocillin, benzathine benzylpenicillin, procaine benzylpenicillin, azidocillin, penamecillin, phenoxymethylpenicillin (V), ... Picillin, benzathine phenoxymethylpenicillin, phenethicillin, cloxacillin (dicloxacillin, flucloxacillin), oxacillin, methicillin, nafcillin, faropenem, biapenem, doripenem, ertapenem, imipenem, meropenem, panipenem, tomopenem, razupenem, cefazolin, cephacetrile, cefadroxil, cephalexin, cephaloglycin, cephalonium, cephaloridine, cephalothin, cephapirin, cefatrizine, cefazedone, cefazaflur, cephradine, cefroxine Xadine, ceftezole, cefaclor, cefamandole, cefminox, cefonicid, ceforanide, cefotiam, cefprozil, cefbuperazone, cefuroxime, cefuzonam, cefoxitin, cefotetan, cefmetazole, loracarbef, cefixime, ceftazidime, ceftriaxone, cefcapene, cefdaloxime, cefdinir, cefditoren, cefetamet, cefmenoxime, cefodizime, cefoperazone, cefotaxime, cefpimizole, cefpiramide, cefpodoxime, cefsulodin, cefteram Item 77. The pharmaceutical composition of Item 75 or 76, wherein the compound is selected from the group consisting of ceftibuten, ceftiolene, ceftizoxime, flomoxef, latamoxef, cefepime, cefozopran, cefpirome, cefquinome, ceftobiprole, ceftaroline, CXA-101, RWJ-54428, MC-04546, ME1036, BAL30072, SYN2416, ceftiofur, cefquinome, cefovecin, aztreonam, tigenonam, carumonam, RWJ-442831, RWJ-333441, and RWJ-333442.[Item 78] The pharmaceutical composition of Item 76 or 77, wherein the β-lactam drug is selected from ceftazidime, biapenem, doripenem, ertapenem, imipenem, meropenem, or panipenem. [Item 79] The pharmaceutical composition of Item 76 or 77, wherein the β-lactam drug is selected from aztreonam, tigenonam, BAL30072, SYN2416, or carumonam. [Item 80] The pharmaceutical composition of Item 73, which is administered together with an additional drug. [Item 81] The pharmaceutical composition of Item 80, wherein the additional drug is selected from an antibacterial agent, an antifungal agent, an antiviral agent, an anti-inflammatory agent, or an antiallergic agent. [Item 82] The pharmaceutical composition of Item 80 or 81, wherein the additional drug is a β-lactam drug.[Item 83] The beta-lactam drug as an additional drug is amoxicillin, ampicillin (pivampicillin, hetacillin, bacampicillin, metampicillin, talampicillin), epicillin, carbenicillin (carindacillin), ticarcillin, temocillin, azlocillin, piperacillin, mezlocillin, mecillinam (pivmecillinam), sulbenicillin, benzylpenicillin (G), clometocillin, benzathine benzylpenicillin, procaine benzylpenicillin, azidocillin, penamecillin, phenoxymethylpenicillin (V), ... Picillin, benzathine phenoxymethylpenicillin, phenethicillin, cloxacillin (dicloxacillin, flucloxacillin), oxacillin, methicillin, nafcillin, faropenem, biapenem, doripenem, ertapenem, imipenem, meropenem, panipenem, tomopenem, razupenem, cefazolin, cephacetrile, cefadroxil, cephalexin, cephaloglycin, cephalonium, cephaloridine, cephalothin, cephapirin, cefatrizine, cefazedone, cefazaflur, cephradine, cefroxine Xadine, ceftezole, cefaclor, cefamandole, cefminox, cefonicid, ceforanide, cefotiam, cefprozil, cefbuperazone, cefuroxime, cefuzonam, cefoxitin, cefotetan, cefmetazole, loracarbef, cefixime, ceftazidime, ceftriaxone, cefcapene, cefdaloxime, cefdinir, cefditoren, cefetamet, cefmenoxime, cefodizime, cefoperazone, cefotaxime, cefpimizole, cefpiramide, cefpodoxime, cefsulodin, cefteram Item 83. The pharmaceutical composition of Item 81 or 82, wherein the compound is selected from the group consisting of ceftibuten, ceftiolene, ceftizoxime, flomoxef, latamoxef, cefepime, cefozopran, cefpirome, cefquinome, ceftobiprole, ceftaroline, CXA-101, RWJ-54428, MC-04546, ME1036, BAL30072, SYN2416, ceftiofur, cefquinome, cefovecin, aztreonam, tigenonam, carumonam, RWJ-442831, RWJ-333441, and RWJ-333442.[Item 84] The pharmaceutical composition of Item 82 or 83, wherein the β-lactam drug is selected from the group consisting of ceftazidime, biapenem, doripenem, ertapenem, imipenem, meropenem, and panipenem. [Item 85] The pharmaceutical composition of Item 82 or 83, wherein the β-lactam drug is selected from the group consisting of aztreonam, tigenonam, BAL30072, SYN2416, and carumonam. [Item 86] The compound of any one of the preceding items, or a pharmaceutically acceptable salt thereof, for treating a bacterial infection. [Item 87] The compound of any one of the preceding items, or a pharmaceutically acceptable salt thereof, wherein the bacterial infection is a bacterial infection involving a bacterium capable of possessing β-lactamase. [Item 88] The compound according to any one of the preceding items, or a pharmaceutically acceptable salt thereof, wherein the bacterial infection is sepsis, febrile neutropenia, bacterial meningitis, bacterial endocarditis, otitis media, sinusitis, pneumonia, lung abscess, empyema, secondary infection of chronic respiratory lesions, pharyngitis / laryngitis, tonsillitis, osteomyelitis, arthritis, peritonitis, intraperitoneal abscess, cholecystitis, cholangitis, liver abscess, deep skin infection, lymphangitis / lymphadenitis, secondary infection of trauma / burn, surgical wound, or the like, urinary tract infection, genital infection, eye infection, or dental infection. [Item 89] A pharmaceutical comprising the compound of any one of the preceding items or a pharmaceutically acceptable salt thereof in combination with at least one drug selected from the group consisting of therapeutic agents for sepsis, febrile neutropenia, bacterial meningitis, bacterial endocarditis, otitis media, sinusitis, pneumonia, lung abscess, empyema, secondary infections of chronic respiratory lesions, pharyngitis / laryngitis, tonsillitis, osteomyelitis, arthritis, peritonitis, intraperitoneal abscess, cholecystitis, cholangitis, liver abscess, deep skin infections, lymphangitis / lymphadenitis, secondary infections such as those from trauma, burns, and surgical wounds, urinary tract infections, genital infections, eye infections, and dental infections. [Item 90] A pharmaceutical composition comprising a β-lactam drug, wherein the pharmaceutical composition is administered together with the compound of any one of the preceding items or a pharmaceutically acceptable salt thereof. [Item 91] A method for treating a bacterial infection, comprising administering to a patient in need thereof a therapeutically effective amount of the compound according to any one of the preceding items or a pharmaceutically acceptable salt thereof.[Item 92] The method of any one of the preceding items, wherein the bacterial infection is a bacterial infection involving a bacterium capable of possessing β-lactamase. [Item 93] The method of any one of the preceding items, wherein the bacterial infection is sepsis, febrile neutropenia, bacterial meningitis, bacterial endocarditis, otitis media, sinusitis, pneumonia, lung abscess, empyema, secondary infection of a chronic respiratory lesion, pharyngitis / laryngitis, tonsillitis, osteomyelitis, arthritis, peritonitis, intraperitoneal abscess, cholecystitis, cholangitis, liver abscess, deep skin infection, lymphangitis / lymphadenitis, secondary infection of trauma / burn, surgical wound, etc., urinary tract infection, genital infection, eye infection, or dental infection. [Item 94] The method of any one of the preceding items, wherein the method is administered together with an additional drug.

[0011] It is contemplated that the present invention may provide one or more of the above-described features in combinations other than those explicitly stated. Still further embodiments and advantages of the present invention will be recognized by those skilled in the art upon reading and understanding the following detailed description, if necessary.

[0012] The compound of the present invention has an excellent inhibitory effect against serine-β-lactamases having a serine residue in the enzyme active center. In addition, a more excellent embodiment of the compound of the present invention is that it has a broad β-lactamase inhibitory effect against multiple types of β-lactamases and zinc (Zn) in the enzyme active center. ２＋ Therefore, the compound of the present invention, used alone or in combination with a β-lactam drug, is useful as a therapeutic and / or preventive agent for bacterial infections involving bacteria capable of possessing β-lactamase, specifically sepsis, febrile neutropenia, bacterial meningitis, bacterial endocarditis, otitis media, sinusitis, pneumonia, lung abscess, empyema, secondary infections of chronic respiratory lesions, pharyngitis / laryngitis, tonsillitis, osteomyelitis, arthritis, peritonitis, intraperitoneal abscess, cholecystitis, cholangitis, liver abscess, deep skin infections, lymphangitis / lymphadenitis, secondary infections of trauma / burn, surgical wounds, and the like, urinary tract infections, genital infections, eye infections, or dental infections.

[0013] The present invention will be described in more detail below. Throughout this specification, singular expressions should be understood to include the plural concept unless otherwise specified. Therefore, singular articles (e.g., "a," "an," "the," etc. in English) should be understood to include the plural concept unless otherwise specified. In addition, it should be understood that the terms used in this specification are used in the sense commonly used in the art unless otherwise specified. Therefore, unless otherwise defined, all technical and scientific terms used in this specification have the same meaning as commonly understood by those skilled in the art to which this invention belongs. In the event of conflict, this specification (including definitions) shall prevail. First, the terms and general techniques used in this specification will be explained.

[0014] The term "group" refers to a monovalent group unless otherwise specified. Examples of non-monovalent groups include alkylene groups (divalent). In addition, in the following description of substituents, etc., the term "group" may be omitted in some cases.

[0015] In this specification, when defined as "optionally substituted" or "substituted," the number of substituents is not particularly limited as long as substitution is possible, and is one or more. Furthermore, unless otherwise specified, the description of each substituent also applies when that substituent is a part of or a substituent for another substituent.

[0016] The substituents in "optionally substituted" are selected from the following group of substituents α, and may be substituted with 1 to 5 identical or different substituents. There are no particular limitations on the type of substituent, but when the atom to which a substituent is bonded is an oxygen atom, a nitrogen atom, or a sulfur atom, the substituents are limited to those below in which the atom to which the substituent is bonded is a carbon atom. The group of substituents α includes: 1) halogen atoms, 2) hydroxyl groups, 3) carboxyl groups, 4) cyano groups, 5) sulfanyl groups, 6) nitro groups, 7) C １－６ Alkyl group 8) C ２－６ Alkenyl group 9) C ２－６ Alkynyl group 10) C １－６ Alkoxy group 11) C１－６ Alkylthio group 12) C １－６ Alkylcarbonyl group 13) C １－６ an alkylsulfonyl group (wherein each of the substituents 7) to 13) may be substituted with 1 to 5 identical or different substituents selected from the substituent group β); 14) C ３－１０ Alicyclic group 15)C ３－１０ Alicyclic oxy group 16) C ６－１０ 17) 5- or 6-membered heteroaryloxy group; 18) 4- to 10-membered non-aryl heterocyclic oxy group; 19) C ３－１０ Alicyclic thio group 20) C ６－１０ 21) 5- or 6-membered heteroarylthio group; 22) 4- to 10-membered non-aryl heterocyclic thio group; 23) C ６－１０ 24) 5- or 6-membered heteroaryl 25) 4- to 10-membered non-aryl heterocycle 26) C ３－１０ Alicyclic carbonyl group 27) C ６－１０ 28) an arylcarbonyl group; 29) a 4- to 10-membered non-aryl heterocyclic carbonyl group; 30) a 4- to 10-membered non-aryl heterocyclic carbonylamino group; 31) C ３－１０ Alicyclic sulfonyl group 32) C ６－１０ 33) a 5- or 6-membered heteroarylsulfonyl group; 34) a 4- to 10-membered non-aryl heterocyclic sulfonyl group; (provided that each of the substituents in 14) to 34) is selected from 1 to 5 of the substituent group β or the group 1) C １－６ 35) -NR, which may be substituted with an alkyl group １０ａ R １１ａ 36) -SO ２ -R １０ｂ 37) -SO ２ -NR １０ｂ R １１ｂ 38)-NR １０ｃ -C(=O)R １１ｃ 39)-NR １０ｄ -C(=O)OR １１ｄ 40)-NR １２ａ -C(=O)NR １０ｅ R １１ｅ 41)-NR １０ｆ -C(=S)R１１ｆ 42)-NR １０ｇ -C(=S)OR １１ｇ 、 43)-NR １２ｂ -C(=S)NR １０ｈ R １１ｈ 44)-NR １０ｉ -SO ２ -R １１ｉ 45)-NR １２ｃ -SO ２ -NR １０ｊ R １１ｊ 46)-C(=O)OR １０ｋ 47)-C(=O)NR １０ｌ R １１ｋ 48)-C(=O)NR １０ｍ OR １１ｌ 49)-C(=O)NR １２ｄ -NR １０ｎ R １１ｍ 50)-C(=S)OR １０ｏ 51)-C(=S)NR １０ｐ R １１ｎ 52)-C(=S)NR １０ｑ OR １１ｏ 53)-C(=S)NR １２ｅ -NR １０ｒ R １１ｐ 54)-C(=NR １３ａ )R １０ｓ 55)-C(=NR １３ｂ )CHO 56)-C(=NR １３ｃ )NR １０ｔ R １１ｑ 57)-C(=NR １３ｄ )NR １２ｆ -NR １０ｕ R １１ｒ 58)-NR １７ｃ -C(=NR １３ｋ )R １７ｄ 59)-NR １２ｇ -C(=NR １３ｅ )-NR １０ｖ R １１ｓ 60)-NR １４ -C(=NR １３ｆ )-NR １２ｈ -NR １０ｗ R １１ｔ 61)-OC(=O)R １０ｘ 62)-OC(=O)OR １０ｙ63)-OC(=O)NR １０ｚ１ R １１ｕ 64)-NR １２ｉ -NR １０ｚ２ R １１ｖ 65)-NR １０ｚ３ OR １１ｗ 66)-C(=N-OR １３ａ ) R １０ｓ 67)-C(=N-OR １３ｂ )CHO 68)-C(=N-OR １３ｃ ) NR １０ｔ R １１ｑ 69)-C(=N-OR １３ｄ ) NR １２ｆ -NR １０ｕ R １１ｒ 70)-C(=O)NR １２ｊ -S(=O) ２ -R １０ａ１ 71)-C(=O)NR １２ｋ -S(=O) ２ -NR １０ａ２ R １１ｘ The substituent group β includes 1) a halogen atom, 2) a hydroxyl group, 3) a carboxyl group, 4) a cyano group, 5) a C ３－１０ Alicyclic group, 6)C １－６ an alkoxy group, 7) C ３－１０ 8) an alicyclic oxy group, C １－６ an alkylthio group, 9) a 5- or 6-membered heteroarylthio group, 10) C ６－１０ aryl, 11) 5- or 6-membered heteroaryl, 12) 4- to 10-membered non-aryl heterocycle, 13) C １－６ Alkylcarbonyl group, 14) C ３－１０ alicyclic carbonyl group, 15) C ６－１０ 16) an arylcarbonyl group, 17) a 4- to 10-membered non-aryl heterocyclic carbonyl group, 18) —NR １５ａ R １６ａ , 19)-SO ２ -NR １５ｂ R １６ｂ , 20)-NR １５ｃ -C(=O)R １６ｃ 21) -NR １７ａ -C(=O)NR １５ｄ R１６ｄ , 22)-C(=O)NR １５ｅ R １６ｅ , 23)-C(=NR １３ｇ ) R １５ｆ , 24)-C(=NR １３ｈ ) NR １５ｇ R １６ｆ 25)-NR １６ｇ -C(=NR １３ｉ ) R １５ｈ 26) -NR １７ｂ -C(=NR １３ｊ )-NR １５ｉ R １６ｈ 27)-C(=N-OR １３ｇ ) R １５ｆ , 28)-C(=N-OR １３ｈ ) NR １５ｇ R １６ｆ (However, in the substituent group β, each of the substituents 5) to 17) is a halogen atom, a hydroxyl group, a cyano group, a carboxyl group, -NR １８ａ R １８ｂ and R １３ａ , R １３ｂ , R １３ｃ , R １３ｄ , R １３ｅ , R １３ｆ , R １３ｇ , R １３ｈ , R １３ｉ , R １３ｊ , R １３ｋ are each independently the same or different and represent a hydrogen atom, a hydroxyl group, or C １－６ Alkyl group, C １－６ is an alkoxy group, R １０ａ , R １０ｂ , R １０ｃ , R １０ｄ , R １０ｅ , R １０ｆ , R １０ｇ , R １０ｈ , R １０ｉ , R １０ｊ , R １０ｋ , R １０ｌ , R １０ｍ , R １０ｎ , R １０ｏ , R １０ｐ , R １０ｑ , R １０ｒ , R１０ｓ 、R １０ｔ 、R １０ｕ 、R １０ｖ 、R １０ｗ 、R １０ｘ 、R １０ｙ 、R １０ａ１ 、R １０ａ２ 、R １０ｚ１ 、R １０ｚ２ 、R １０ｚ３ 、R １１ａ 、R １１ｂ 、R １１ｃ 、R １１ｄ 、R １１ｅ 、R １１ｆ 、R １１ｇ 、R １１ｈ 、R １１ｉ 、R １１ｊ 、R １１ｋ 、R １１ｌ 、R １１ｍ 、R １１ｎ 、R １１ｏ 、R １１ｐ 、R １１ｑ 、R １１ｒ 、 １１ｓ 、R １１ｔ 、R １１ｕ 、R １１ｖ 、R １１ｗ 、R １１ｘ 、R １２ａ 、R １２ｂ 、R １２ｃ 、R １２ｄ 、R １２ｅ 、R １２ｆ 、R １２ｇ 、R １２ｈ 、R １２ｉ 、R １２ｊ 、R １２ｋ 、R １４ 、R １５ａ 、R １５ｂ 、R １５ｃ 、R １５ｄ 、R １５ｅ 、R １５ｆ 、R １５ｇ 、R １５ｈ 、R １５ｉ 、R １６ａ 、R １６ｂ 、R １６ｃ 、R １６ｄ 、R １６ｅ 、R １６ｆ 、R １６ｇ 、R １６ｈ 、R １７ａ 、R １７ｂ, R １７ｃ , R １７ｄ are each independently the same or different and represent a hydrogen atom, a 5- or 6-membered non-aryl heterocycle, or C １－６ alkyl group (said 5- or 6-membered non-aryl heterocycle and said C １－６ The alkyl groups are each independently a hydroxyl group, a cyano group, a C １－６ Alkoxy group, —NR １８ａ R １８ｂ , a carboxyl group, and —C(═O)NR １８ｃ R １８ｄ and R １８ａ , R １８ｂ , R １８ｃ and R １８ｄ are each independently the same or different and represent a hydrogen atom or C １－６ It is an alkyl group.

[0017] The substituents in "optionally substituted" are preferably the following. The substituent group α is preferably: 1) a halogen atom, 2) a hydroxyl group, 3) a carboxyl group, 4) a cyano group, 5) a C １－６ Alkyl group 6) C １－６ Alkoxy group 7) C １－６ Alkylthio group 8) C １－６ an alkylcarbonyl group (wherein each of the substituents 5) to 8) may be substituted with 1 to 5 identical or different substituents selected from the substituent group β); 9) C ３－１０ Alicyclic group 10)C ３－１０ Alicyclic oxy group 11) C ６－１０ 12) 5- or 6-membered heteroaryloxy group; 13) 4- to 10-membered non-aryl heterocyclic oxy group; 14) C ３－１０ Alicyclic thio group 15) C ６－１０ 16) 5- or 6-membered heteroarylthio group; 17) 4- to 10-membered non-aryl heterocyclic thio group; 18) C ６－１０ Aryl 19) 5- or 6-membered heteroaryl 20) 4- to 10-membered non-aryl heterocycle 21) C ３－１０ Alicyclic carbonyl group 22) C ６－１０23) an arylcarbonyl group; 24) a 4- to 10-membered non-aryl heterocyclic carbonyl group; (provided that each of the substituents in 9) to 24) is selected from 1 to 5 of the substituent group β or the above-mentioned 1) C １－６ 25) -NR, which may be substituted with an alkyl group １０ａ R １１ａ 26) -SO ２ -NR １０ｂ R １１ｂ 27) -NR １０ｃ -C(=O)R １１ｃ 28)-NR １２ａ -C(=O)NR １０ｄ R １１ｄ 29)-NR １０ｅ -SO ２ -R １１ｅ 30)-NR １２ｂ -SO ２ -NR １０ｆ R １１ｆ 31)-C(=O)NR １０ｇ R １１ｇ 32) -C(=NR １３ａ ) R １０ｈ 33) -C(=NR １３ｂ ) NR １０ｉ R １１ｈ 34)-NR １１ｆ -C(=NR １３ｃ ) R １０ｇ 35)-NR １２ｃ -C(=NR １３ｄ )-NR １０ｊ R １１ｉ 36)-C(=N-OR １３ａ ) R １０ｈ 37)-C(=N-OR １３ｂ ) NR １０ｉ R １１ｈ The substituent group β is preferably a group selected from the group consisting of: 1) a halogen atom, 2) a hydroxyl group, 3) a cyano group, and 4) C ３－１０ Alicyclic group 5)C １－６ Alkoxy group 6) C １－６ 7) an alkylthio group; 8) a 5- or 6-membered heteroarylthio group; 9) a 4- to 10-membered non-aryl heterocycle; 10) C １－６ Alkylcarbonyl group 11) C ３－１０Alicyclic carbonyl group 12) C ６－１０ 13) an arylcarbonyl group; 14) a 4- to 10-membered non-aryl heterocyclic carbonyl group; 15) —NR １５ａ R １６ａ 16) -NR １５ｂ -C(=O)R １６ｂ 17) -NR １７ａ -C(=O)NR １５ｃ R １６ｃ 18)-C(=O)NR １５ｄ R １６ｄ 19) -C(=NR １３ｅ ) R １５ｅ 20) -C(=NR １３ｆ ) NR １５ｆ R １６ｅ 21) -NR １６ｆ -C(=NR １３ｇ ) R １５ｇ 22) -NR １７ｂ -C(=NR １３ｈ )-NR １５ｈ R １６ｇ 23)-C(=N-OR １３ｅ ) R １５ｅ 24)-C(=N-OR １３ｆ ) NR １５ｆ R １６ｅ (However, in the substituent group β, each of the substituents 4) to 14) is a halogen atom, a hydroxyl group, a cyano group, a carboxyl group, -NR １８ａ R １８ｂ and R １３ａ , R １３ｂ , R １３ｃ , R １３ｄ , R １３ｅ , R １３ｆ , R １３ｇ , R １３ｈ are each independently the same or different and represent a hydrogen atom, a hydroxyl group, or C １－６ Alkyl group, C １－６ is an alkoxy group, R １０ａ , R １０ｂ , R １０ｃ , R １０ｄ , R １０ｅ , R １０ｆ , R １０ｇ , R１０ｈ , R １０ｉ , R １０ｊ , R １１ａ , R １１ｂ , R １１ｃ , R １１ｄ , R １１ｅ , R １１ｆ , R １１ｇ , R １１ｈ , R １１ｉ , R １２ａ , R １２ｂ , R １２ｃ , R １５ａ , R １５ｂ , R １５ｃ , R １５ｄ , R １５ｅ , R １５ｆ , R １５ｇ , R １５ｈ , R １６ａ , R １６ｂ , R １６ｃ , R １６ｄ , R １６ｅ , R １６ｆ , R １６ｇ , R １７ａ , R １７ｂ are each independently the same or different and represent a hydrogen atom or C １－６ Alkyl group (the group is a hydroxyl group, a cyano group, C １－６ Alkoxy group, —NR １８ａ R １８ｂ and R １８ａ , R １８ｂ are each independently the same or different and represent a hydrogen atom or C １－６ It is an alkyl group.

[0018] More preferred examples of the substituent in "optionally substituted" include the following substituents. The substituent group α is more preferably: 1) a halogen atom, 2) a hydroxyl group, 3) a cyano group, 4) a C １－６ Alkyl group 5) C １－６ Alkoxy group 6) C １－６ Alkylthio group 7) C １－６an alkylcarbonyl group (wherein each of the substituents 4) to 7) may be substituted with 1 to 5 identical or different substituents selected from substituent group β); 8) a 5- or 6-membered heteroaryloxy group; 9) a 4- to 10-membered non-aryl heterocyclic oxy group; 10) a 5- or 6-membered heteroarylthio group; 11) a 4- to 10-membered non-aryl heterocyclic thio group; 12) C ６－１０ 13) 5- or 6-membered heteroaryl; 14) 4- to 10-membered non-aryl heterocycle (provided that each of the substituents in 4) to 14) is selected from 1 to 5 of the substituent group β or the above 1) C １－６ 15) -NR, which may be substituted with an alkyl group １０ａ R １１ａ 16) -NR １１ｂ -C(=O)R １０ｂ 17) -NR １２ａ -C(=O)NR １０ｃ R １１ｃ 18)-C(=O)NR １０ｄ R １１ｄ 19) -C(=NR １３ａ ) R １０ｅ 20) -C(=NR １３ｂ ) NR １０ｆ R １１ｅ 21) -NR １１ｆ -C(=NR １３ｃ ) R １０ｇ 22) -NR １２ｂ -C(=NR １３ｄ )-NR １０ｈ R １１ｇ 23)-C(=N-OR １３ａ ) R １０ｅ 24)-C(=N-OR １３ｂ ) NR １０ｆ R １１ｅ The substituent group β is more preferably: 1) a halogen atom, 2) a hydroxyl group, 3) a cyano group, 4) —NR １５ａ R １６ａ , 5)-NR １５ｂ -C(=O)R １６ｂ , 6)-NR １７ａ -C(=O)NR １５ｃ R １６ｃ , 7)-C(=O)NR １５ｄ R １６ｄ , 8)-C(=NR １３ｅ) R １５ｅ , 9)-C(=NR １３ｆ ) NR １５ｆ R １６ｅ , 10)-NR １６ｆ -C(=NR １３ｇ ) R １５ｇ , 11)-NR １７ｂ -C(=NR １３ｈ )-NR １５ｈ R １６ｇ 12)-C(=N-OR １３ｅ ) R １５ｅ , 13)-C(=N-OR １３ｆ ) NR １５ｆ R １６ｅ and R １３ａ , R １３ｂ , R １３ｃ , R １３ｄ , R １３ｅ , R １３ｆ , R １３ｇ , R １３ｈ are each independently the same or different and represent a hydrogen atom, a hydroxyl group, or C １－６ Alkyl group, C １－６ is an alkoxy group, R １０ａ , R １０ｂ , R １０ｃ , R １０ｄ , R １０ｅ , R １０ｆ , R １０ｇ , R １０ｈ , R １１ａ , R １１ｂ , R １１ｃ , R １１ｄ , R １１ｅ , R １１ｆ , R １１ｇ , R １２ａ , R １２ｂ , R １５ａ , R １５ｂ , R １５ｃ , R １５ｄ , R １５ｅ , R １５ｆ , R １５ｇ , R １５ｈ , R １６ａ , R １６ｂ , R １６ｃ , R １６ｄ , R １６ｅ , R １６ｆ , R １６ｇ , R １７ａ , R １７ｂare each independently the same or different and represent a hydrogen atom or C １－６ Alkyl group (the group is a hydroxyl group, a cyano group, C １－６ Alkoxy group, —NR １８ａ R １８ｂ and R １８ａ , R １８ｂ are each independently the same or different and represent a hydrogen atom or C １－６ It is an alkyl group.

[0019] "C １－６ " means that the number of carbon atoms is 1 to 6. The same applies to other numbers, for example, "C １－４ " means that the number of carbon atoms is 1 to 4.

[0020] The term "heteroatom" refers to an oxygen atom, a nitrogen atom, a sulfur atom, or the like.

[0021] "Halogen atom" means a fluorine atom, chlorine atom, bromine atom, or iodine atom. A fluorine atom or chlorine atom is preferred. A fluorine atom is more preferred. A "halogen atom" may also be referred to as "halogen."

[0022] "C １－６ "Alkyl group" means a saturated hydrocarbon group having 1 to 6 carbon atoms, either linear or branched. １－６ As the "alkyl group", preferably "C １－４ alkyl group," and more preferably "C １－３ alkyl group," and more preferably "C １－２ "C alkyl group." １－６ Specific examples of the "alkyl group" include, but are not limited to, methyl, ethyl, propyl, butyl, isopropyl, isobutyl, tert-butyl, sec-butyl, isopentyl, neopentyl, tert-pentyl, 1,2-dimethylpropyl, and the like.

[0023] "C ２－６ "Alkenyl group" means a straight-chain or branched unsaturated hydrocarbon group containing one or more carbon-carbon double bonds and having 2 to 6 carbon atoms.２－６ As the "alkenyl group", preferably "C ２－４ "C is an alkenyl group." ２－６ Specific examples of the "alkenyl group" include, but are not limited to, a vinyl group, a 1-propylenyl group, a 2-propylenyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 2-methyl-1-propylenyl group, and a 2-methyl-2-propylenyl group.

[0024] "C ２－６ The term "alkynyl group" means a straight-chain or branched unsaturated aliphatic hydrocarbon group having one or more triple bonds. ２－６ As the "alkynyl group", preferably "C ２－４ Specific examples include, but are not limited to, an ethynyl group, a 1-propynyl group, a 2-propynyl group, a 1-butynyl group, a 1-methyl-2-propynyl group, a 3-butynyl group, a 1-pentynyl group, and a 1-hexynyl group.

[0025] "C ３－２０ The term "alicyclic group" refers to a monocyclic or bicyclic non-aromatic hydrocarbon ring having 3 to 20 carbon atoms, and includes those having a partially unsaturated bond, a partially bridged structure, a partially spiro-bonded structure, and one or two carbonyl structures. The term "alicyclic group" encompasses a cycloalkyl group, a cycloalkenyl group, and a cycloalkynyl group. ３－２０ As the "alicyclic group", preferably "C ３－１０ alicyclic group," and more preferably "C ３－６ "C is an alicyclic group." ３－２０ Specific examples of the "alicyclic group" include, but are not limited to, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a cyclohexadinyl group, a cycloheptadinyl group, a cyclooctaadinyl group, adamantyl, and norbornyl. ３－２０ Specific examples of the "alicyclic group" include, but are not limited to, those having the structures shown below.

[0026] Also, "C３－２０ The "alicyclic group" also includes compounds in which an aromatic ring is condensed. Specific examples include the groups shown below.

[0027] "C ３－１０ The "alicyclic group" is defined as "C ３－２０ Among the "alicyclic groups," "C ３－１０ The term "alicyclic group" refers to a substituent in which the alicyclic group is a monovalent group.

[0028] "C ６－１０ "Aryl" means a monocyclic or bicyclic aromatic hydrocarbon ring having 6 to 10 carbon atoms, and specific examples thereof include a phenyl group, a 1-naphthyl group, and a 2-naphthyl group. ６－１０ As the aryl, preferably C ６ or C １０ Examples of aryl include the following.

[0029] The term "5- or 6-membered heteroaryl" refers to a monocyclic aromatic heterocycle consisting of 5 to 6 atoms, containing 1 to 4 identical or different heteroatoms selected from the group consisting of oxygen, nitrogen, and sulfur atoms.

[0030] "5- to 10-membered heteroaryl" means a monocyclic or bicyclic aromatic heterocycle consisting of 5 to 10 atoms containing 1 to 4 identical or different heteroatoms selected from the group consisting of oxygen, nitrogen, and sulfur atoms.

[0031] "9- or 10-membered heteroaryl" means a bicyclic aromatic heterocycle consisting of 9 to 10 atoms containing 1 to 4 identical or different heteroatoms selected from the group consisting of oxygen, nitrogen, and sulfur atoms.

[0032] The term "5- or 6-membered nitrogen-containing heteroaryl" refers to a monocyclic aromatic heterocycle consisting of 5 to 6 atoms, which contains one nitrogen atom and 0 to 3 identical or different heteroatoms selected from the group consisting of oxygen atoms, nitrogen atoms, and sulfur atoms.

[0033] Specific examples of "6-membered heteroaryl" include, but are not limited to, pyridine, pyridazine, pyrimidine, pyrazine, and the like.

[0034] Specific examples of the "5-membered heteroaryl" include, but are not limited to, thiophene, pyrrole, thiazole, isothiazole, pyrazole, imidazole, furan, oxazole, isoxazole, oxadiazole, thiadiazole, triazole, tetrazole, etc., preferably triazole, tetrazole, or thiadiazole, more preferably thiadiazole.

[0035] Specific examples of the "5- or 6-membered heteroaryl" include the specific examples of the "5-membered heteroaryl" and "6-membered heteroaryl" mentioned above.

[0036] The term "4- to 20-membered non-aryl heterocycle" refers to a monocyclic or bicyclic non-aromatic heterocycle consisting of 4 to 20 atoms, containing one or two identical or different heteroatoms selected from the group consisting of oxygen, nitrogen, and sulfur atoms, and includes those having a partially unsaturated bond, a partially bridged structure, and a partially spiro-bonded structure. The non-aryl heterocycle may form a condensed ring with an aryl or heteroaryl. For example, C ６－１０ A heterocycle also includes a ring fused with an aryl or a 5- or 6-membered heteroaryl. The non-aryl heterocycle may contain one or two carbonyls, thiocarbonyls, sulfinyls, or sulfonyls. For example, cyclic groups such as lactams, thiolactams, lactones, thiolactones, cyclic imides, cyclic carbamates, and cyclic thiocarbamates are also included in the non-aryl heterocycle. Here, the oxygen atoms of the carbonyls, sulfinyls, and sulfonyls and the sulfur atoms of the thiocarbonyls are not included in the number of 4 to 20 members (ring size) and the number of heteroatoms constituting the ring. Specific examples of "4- to 20-membered non-aryl heterocycles" include, but are not limited to, azetidine, pyrrolidine, piperidine, piperazine, morpholine, homopiperidine, oxetane, tetrahydrofuran, tetrahydropyran, and the like, as well as those with the structures shown below.

[0037] Specific examples of the "4- to 20-membered non-aryl heterocycle" having a partial bridge and spiro structure include, but are not limited to, those having the structures shown below.

[0038] The term "4- to 20-membered nitrogen-containing non-aryl heterocycle" refers to a monocyclic or bicyclic non-aromatic heterocycle composed of 4 to 20 atoms, which contains one nitrogen atom and, in addition, zero or one identical or different heteroatoms selected from the group consisting of oxygen atoms, nitrogen atoms, and sulfur atoms, and includes those having a partially unsaturated bond, a partially bridged structure, and a partially spiro-formed heterocycle.

[0039] The "4- to 10-membered non-aryl heterocycle" means a substituent in which the "4- to 10-membered non-aryl heterocycle" is a monovalent group among the above-mentioned "4- to 20-membered non-aryl heterocycles".

[0040] The "4- to 10-membered nitrogen-containing non-aryl heterocycle" means a substituent in which the "4- to 10-membered nitrogen-containing non-aryl heterocycle" is a monovalent group, among the above-mentioned "4- to 20-membered nitrogen-containing non-aryl heterocycles".

[0041] The "5- to 7-membered non-aryl heterocycle" means a substituent in which the "5- to 7-membered non-aryl heterocycle" is a monovalent group among the above "4- to 20-membered non-aryl heterocycles".

[0042] The "4- to 7-membered non-aryl heterocycle" means a substituent in which the "4- to 7-membered non-aryl heterocycle" is a monovalent group among the above-mentioned "4- to 20-membered non-aryl heterocycles".

[0043] Specific examples of the "four-membered non-aryl heterocycle" include, but are not limited to, azetidine, oxetane, thietane, and the like.

[0044] Specific examples of the "four-membered non-aryl heterocycle" having a partial unsaturated bond include, but are not limited to, those having the structures shown below.

[0045] Specific examples of the "5-membered non-aryl heterocycle" include, but are not limited to, pyrrolidine, pyrrolidone, oxazolidinone, tetrahydrofuran, tetrahydrothiophene, and the like.

[0046] Specific examples of the "five-membered non-aryl heterocycle" having a partial unsaturated bond include, but are not limited to, those having the structures shown below.

[0047] Specific examples of the "five-membered non-aryl heterocycle" having a partially bridged structure include, but are not limited to, those having the structures shown below.

[0048] Specific examples of the "5-membered non-aryl heterocycle" containing carbonyl, thiocarbonyl, etc. include, but are not limited to, those having the structures shown below.

[0049] Specific examples of the "6-membered non-aryl heterocycle" include, but are not limited to, piperidine, piperazine, morpholine, tetrahydropyran, tetrahydrothiopyran, and the like.

[0050] Specific examples of the "six-membered non-aryl heterocycle" having a partial unsaturated bond include, but are not limited to, those having the structures shown below.

[0051] Specific examples of the "six-membered non-aryl heterocycle" having a partially bridged structure include, but are not limited to, those having the structures shown below.

[0052] "C １－６ The "alkoxy group" is "C １－６ alkyloxy group, １－６ The alkyl portion is the C １－６ It has the same meaning as alkyl group. １－６ As the "alkoxy group", preferably "C １－４ alkoxy group," and more preferably "C １－３alkoxy group," and more preferably "C １－２ "Alkoxy group." １－６ Specific examples of the "alkoxy group" include, but are not limited to, a methoxy group, an ethoxy group, a propoxy group, a butoxy group, an isopropoxy group, an isobutoxy group, a tert-butoxy group, a sec-butoxy group, an isopentyloxy group, a neopentyloxy group, a tert-pentyloxy group, and a 1,2-dimethylpropoxy group.

[0053] "C ３－１０ The "alicyclic oxy group" is defined as (C ３－１０ (alicyclic group)-O- group, ３－１０ The alicyclic moiety is C ３－１０ It has the same meaning as an alicyclic group. ３－６ The "alicyclic oxy group" is defined as (C ３－６ (alicyclic group)-O- group, ３－６ The alicyclic moiety is C ３－６ It has the same meaning as an alicyclic group. ３－６ As the "alicyclic oxy group", preferably "C ３－５ "C is an alicyclic oxy group." ３－６ Specific examples of the "alicyclic oxy group" include, but are not limited to, a cyclopropyloxy group, a cyclobutyloxy group, a cyclopentyloxy group, a cyclohexyloxy group, and the like.

[0054] "C ６－１０ C of "aryloxy group" ６－１０ The aryl moiety is the C ６－１０ It is synonymous with aryl. ６－１０ As the "aryloxy group," preferably "C ６ Or C １０ "An aryloxy group of C" is an example. ６－１０ Specific examples of the "aryloxy group" include, but are not limited to, a phenoxy group, a 1-naphthyloxy group, and a 2-naphthyloxy group.

[0055] The 5- or 6-membered heteroaryl moiety of the "5- or 6-membered heteroaryloxy group" has the same meaning as the above "5-membered heteroaryl" or "6-membered heteroaryl." Specific examples of the "5- or 6-membered heteroaryloxy group" include, but are not limited to, a pyrazolyloxy group, a triazolyloxy group, a thiazoyloxy group, a thiadiazoyloxy group, a pyridyloxy group, and a pyridazoyloxy group.

[0056] The 4- to 10-membered non-aryl heterocyclic moiety of the "4- to 10-membered non-aryl heterocyclic oxy group" has the same meaning as the above-mentioned "4- to 10-membered non-aryl heterocyclic ring". The "4- to 10-membered non-aryl heterocyclic oxy group" is preferably a "4- to 6-membered non-aryl heterocyclic oxy group". Specific examples of the "4- to 10-membered non-aryl heterocyclic oxy group" include, but are not limited to, a tetrahydrofuranyloxy group, a tetrahydropyranyloxy group, an azetidinyloxy group, a pyrrolidinyloxy group, and a piperidinyloxy group.

[0057] "C １－６ C of "Alkylthio group" １－６ The alkyl portion is the C １－６ It is synonymous with alkyl. １－６ As the "alkylthio group," preferably "C １－４ alkylthio group," and more preferably "C １－３ "C is an alkylthio group." １－６ Specific examples of the "alkylthio group" include, but are not limited to, a methylthio group, an ethylthio group, a propylthio group, a butylthio group, an isopropylthio group, an isobutylthio group, a tert-butylthio group, a sec-butylthio group, an isopentylthio group, a neopentylthio group, a tert-pentylthio group, and a 1,2-dimethylpropylthio group.

[0058] "C ３－１０ The "alicyclic thio group" is defined as (C ３－１０ alicyclic group)-S- group, ３－１０ The alicyclic moiety is the C ３－１０ It has the same meaning as an alicyclic group. ３－１０ The "alicyclic thio group" is preferably "C３－６ "C is an alicyclic thio group." ３－６ Specific examples of the "alicyclic thio group" include, but are not limited to, a cyclopropylthio group, a cyclobutylthio group, a cyclopentylthio group, a cyclohexylthio group, and the like.

[0059] "C ６－１０ C of "arylthio group" ６－１０ The aryl moiety is the C ６－１０ It is synonymous with aryl. ６－１０ As the "arylthio group," preferably "C ６ Or C １０ "An arylthio group represented by the formula "C ６－１０ Specific examples of the "aryloxy group" include, but are not limited to, a phenylthio group, a 1-naphthylthio group, a 2-naphthylthio group, and the like.

[0060] The 5- or 6-membered heteroaryl moiety of the "5- or 6-membered heteroarylthio group" has the same meaning as the above "5-membered heteroaryl" or "6-membered heteroaryl." Specific examples of the "5- or 6-membered heteroarylthio group" include, but are not limited to, a pyrazoylthio group, a triazoylthio group, a thiazoylthio group, a thiadiazoylthio group, a pyridylthio group, and a pyridazoylthio group.

[0061] The 4- to 10-membered non-aryl heterocyclic moiety of the "4- to 10-membered non-aryl heterocyclic thio group" has the same meaning as the above-mentioned "4- to 10-membered non-aryl heterocycle". The "4- to 10-membered non-aryl heterocyclic thio group" is preferably a "4- to 6-membered non-aryl heterocyclic thio group". Specific examples of the "4- to 10-membered non-aryl heterocyclic thio group" include, but are not limited to, a tetrahydropyranylthio group, a piperidinylthio group, and the like.

[0062] "C １－６ The term "alkylcarbonyl group" refers to the above-mentioned "C １－６ "C" means a carbonyl group substituted with an "alkyl group." １－６ As the "alkylcarbonyl group," preferably, "C １－４ "C is an alkylcarbonyl group." １－６Specific examples of the "alkylcarbonyl group" include, but are not limited to, an acetyl group, a propionyl group, and a butyryl group.

[0063] "C ３－１０ The term "alicyclic carbonyl group" refers to the above-mentioned "C ３－１０ "C" means a carbonyl group substituted with an "alicyclic group." ３－１０ As the "alicyclic carbonyl group," preferably, "C ３－６ "C is an alicyclic carbonyl group." ３－１０ Specific examples of the "alicyclic carbonyl group" include, but are not limited to, a cyclopropylcarbonyl group, a cyclopentylcarbonyl group, and the like.

[0064] "C ６－１０ The term "arylcarbonyl group" refers to the above-mentioned "C ６－１０ "C" means a carbonyl group substituted with "aryl." ６－１０ As the "arylcarbonyl group," preferably, "C ６ or C １０ "An arylcarbonyl group of C ６－１０ Specific examples of the "arylcarbonyl group" include, but are not limited to, a benzoyl group, a 1-naphthylcarbonyl group, a 2-naphthylcarbonyl group, and the like.

[0065] The term "5- or 6-membered heteroarylcarbonyl group" refers to a carbonyl group substituted with the above-mentioned "5- or 6-membered heteroaryl". Specific examples of the "5- or 6-membered heteroarylcarbonyl group" include, but are not limited to, a pyrazoylcarbonyl group, a triazoylcarbonyl group, a thiazoylcarbonyl group, a thiadiazoylcarbonyl group, a pyridylcarbonyl group, and a pyridazoylcarbonyl group.

[0066] The term "4- to 10-membered non-aryl heterocyclic carbonyl group" refers to a carbonyl group substituted with the above-mentioned "4- to 10-membered non-aryl heterocycle". The "4- to 10-membered non-aryl heterocyclic carbonyl group" is preferably a "4- to 6-membered non-aryl heterocyclic carbonyl group". Specific examples of the "4- to 10-membered non-aryl heterocyclic carbonyl group" include, but are not limited to, an azetidinylcarbonyl group, a pyrrolidinylcarbonyl group, a piperidinylcarbonyl group, a morpholinylcarbonyl group, and the like.

[0067] "C １－６ The term "alkylsulfonyl group" refers to the same group as defined above in "C １－６ "C" means a sulfonyl group substituted with an "alkyl group." １－６ As the "alkylsulfonyl group", preferably "C １－４ "C is an alkylsulfonyl group." １－６ Specific examples of the "alkylsulfonyl group" include, but are not limited to, a methylsulfonyl group, a propionylsulfonyl group, a butyrylsulfonyl group, and the like.

[0068] "C ３－１０ The term "alicyclic sulfonyl group" refers to the same group as defined above in "C ３－１０ "C" means a sulfonyl group substituted with an "alicyclic group." ３－１０ As the "alicyclic sulfonyl group", preferably "C ３－６ "C is an alicyclic sulfonyl group." ３－１０ Specific examples of the "alicyclic sulfonyl group" include, but are not limited to, a cyclopropylsulfonyl group, a cyclobutylsulfonyl group, a cyclopentylsulfonyl group, a cyclohexylsulfonyl group, and the like.

[0069] "C ６－１０ The term "arylsulfonyl group" refers to the same group as defined above in "C ６－１０ "C" means a sulfonyl group substituted with "aryl." ６－１０ As the "arylsulfonyl group", preferably "C ６ or C １０ "An arylsulfonyl group of C ６－１０Specific examples of the "arylsulfonyl group" include, but are not limited to, a phenylsulfonyl group, a 1-naphthylsulfonyl group, a 2-naphthylsulfonyl group, and the like.

[0070] The term "5- or 6-membered heteroarylsulfonyl group" refers to a sulfonyl group substituted with the above-mentioned "5- or 6-membered heteroaryl". Specific examples of the "5- or 6-membered heteroarylsulfonyl group" include a pyrazoylsulfonyl group, a triazoylsulfonyl group, a thiazoylsulfonyl group, a thiadiazoylsulfonyl group, a pyridylsulfonyl group, a pyridazoylsulfonyl group, and the like.

[0071] "C １－６ The term "alkylene group" refers to a substituent group that has been divalently formed by removing two hydrogen atoms from a saturated hydrocarbon having 1 to 6 carbon atoms. １－３ alkylene group" and "C ２－４ The term "alkylene group" refers to a substituent group formed into a divalent group by removing two hydrogen atoms from a saturated hydrocarbon having 1 to 3 carbon atoms and a saturated hydrocarbon having 2 to 4 carbon atoms, respectively.

[0072] "C ３－１０ The term "cycloalkylene group" refers to a substituent group that has been divalently formed by removing two hydrogen atoms from a saturated cyclic hydrocarbon having 3 to 10 carbon atoms. ３－６ "Cycloalkylene group" and "C ４－６ The term "cycloalkylene group" refers to a substituent formed into a divalent group by removing two hydrogen atoms from a saturated cyclic hydrocarbon having 3 to 6 carbon atoms and a saturated cyclic hydrocarbon having 4 to 6 carbon atoms, respectively.

[0073] "C ６－１０ The term "arylene group" refers to a substituent group that has been divalently formed by removing two hydrogen atoms from an aromatic hydrocarbon having 6 to 10 carbon atoms. ６ The term "arylene group" refers to a substituent group that has been divalently formed by removing two hydrogen atoms from an aromatic hydrocarbon having six carbon atoms.

[0074] A "5- or 6-membered heteroarylene group" refers to a substituent that has been divalently formed by removing two hydrogen atoms from a 5- or 6-membered heteroaryl ring. A "5-membered heteroarylene group" and a "6-membered heteroarylene group" refer to substituents that have been divalently formed by removing two hydrogen atoms from a 5-membered or 6-membered heteroaryl ring, respectively.

[0075] The term "4- to 10-membered non-aryl heterocyclylene group" refers to a divalent substituent formed by removing two hydrogen atoms from a 4- to 10-membered non-aryl heterocycle. The terms "4- to 5-membered non-aryl heterocyclylene group" and "4- to 6-membered non-aryl heterocyclylene group" refer to divalent substituents formed by removing two hydrogen atoms from a 4- to 5-membered or 4- to 6-membered non-aryl heterocycle, respectively.

[0076] R ５ In the description of the specific structure of ４ For a bond that crosses a bond between ring atoms, any substitutable position on the monocyclic or fused polycyclic ring that contains that ring atom may have a variable (e.g., R ６ａ , R ７ａ In the case of a monocyclic 5-membered ring (heteroaryl), for example, (where d is 3) is and L ４ is attached to a ring carbon atom of the 5-membered ring. In the case of a monocyclic 6-membered ring (heteroaryl), for example, (where d is 4) is and L ４ is attached to a ring carbon atom of the 6-membered ring. Alternatively, in the case of a monocyclic 5-membered ring (non-aryl heterocycle), for example, (where d is 7) is and L ４ is attached to a ring carbon atom of the 5-membered ring. In the case of a monocyclic 6-membered ring (non-aryl heterocycle), for example, (where d is 10) is and L ４is attached to a ring carbon atom of the six-membered ring. ５ is the number of substitutable positions on the ring of ４ is the number of substitutable positions excluding the bonding position to

[0077] "Bioisostere" refers to a partial structure (functional group) in a pharmaceutical molecule that plays the same biological role as a certain group (e.g., a carboxyl group) (in the present invention, the concept of bioisosteres also includes prodrug structures). "Carboxylic acid equivalent" refers to a bioisostere of a carboxylic acid. Examples of such carboxylic acid equivalents include, but are not limited to, -SO ３ H, -SO ２ NHR １９ａ , -B(OR ｍ１ ) ２ , -PO(OR ｍ１ ) (OR ｍ２ ), -CONHR １９ａ , -CONHSO ２ R １９ａ , -CONR １９ａ CN, -CONHNHSO ２ R １９ａ and substituents represented by the following formulae (8A), (8B), (8C), (8D), (8E), (8F), (8G), (8H), (8I), (8J), (8K), (8L), (8M), (8N), (8O), (8P), (8Q), (8R), (8S), (8T), (8U), (8V) and (8W) (each of the substituents has 1 to 3 identical or different R １９ｂ and the like, which may be further substituted by [In formulas (8V) and (8W), R ｓ is a hydrogen atom, C １－６ Alkyl group or C ３－１０ Alicyclic group (the C １－６ Alkyl group or C ３－１０ The alicyclic group may be substituted with 1 to 5 halogen atoms, ｔ is a hydrogen atom, C １－６ Alkyl group, C １－６ Alkoxy group (the C １－６ Alkyl group, C１－６ The alkoxy group may be substituted with 1 to 5 halogen atoms), C ３－１０ Alicyclic group, C ３－１０ an alicyclic oxy group, a phenyl group, a phenoxy group, a pyridyl group, or a pyridyloxy group (the C ３－１０ Alicyclic group, C ３－１０ The alicyclic oxy group, phenyl group, phenoxy group, pyridyl group, and pyridyloxy group each contain 1 to 5 halogen atoms, C １－６ Alkyl group, C １－６ and R is either one of the following: １９ａ , R １９ｂ are each independently the same or different and represent a hydrogen atom, a hydroxyl group, or C １－６ Alkyl group, C ６－１０ represents an aryl, a 5- or 6-membered heteroaryl, or a 4- to 10-membered non-aryl heterocycle; ｍ１ is 1) a hydrogen atom, 2) C １－６ an alkyl group; 3) C ３－１０ Alicyclic group, 4)C ６－１０ 5) 5- or 6-membered heteroaryl, or 6) 4- to 10-membered non-aryl heterocycle (provided that each of the substituents in 2) to 6) above may be substituted), provided that R ｍ１ is bonded to the boron atom via an oxygen atom, two R ｍ１ is C ２－４ The alkylene may be taken together with the boron atom and two oxygen atoms to form a 5- to 7-membered non-aryl heterocycle (the alkylene portion of the non-aryl heterocycle may be substituted), and R ｍ２ represents a hydrogen atom, an optionally substituted C １－６ an alkyl group or an optionally substituted C ３－１０ Here, preferably, R ｓ is a hydrogen atom or C １－６ is an alkyl group, R ｔ is a hydrogen atom, C １－６ Alkyl group, C １－６ Alkoxy group, C ３－１０ Alicyclic group or C ３－１０Alternatively, preferably, R １９ａ , R １９ｂ are each independently the same or different and represent a hydrogen atom, a hydroxyl group, or C １－６ It is preferably an alkyl group. ｍ１ , R ｍ２ are each independently the same or different and represent a hydrogen atom, C １－６ alkyl group, or C ３－１０ It is an alicyclic group.

[0078] One embodiment of the compound of the present invention is represented by the following formula (1a) or (1b): In formula (1a) and (1b), G is an oxygen atom, a sulfur atom, or —NR ａ１ -, X is a hydroxyl group, an optionally substituted C １－６ an alkoxy group, or —NR ａ２ R ｂ１ and R ａ１ , R ａ２ and R ｂ１ are each independently the same or different and are each independently selected from the group consisting of: 1) a hydrogen atom, 2) C １－６ an alkyl group; 3) C ３－１０ Alicyclic group, 4)C ６－１０ aryl 5) 5- or 6-membered heteroaryl; 6) 4- to 10-membered non-aryl heterocycle; 7) C １－６ Alkylcarbonyl group, 8) C ３－１０ 9) an alicyclic carbonyl group, C ６－１０ 10) an arylcarbonyl group, 11) a 5- or 6-membered heteroarylcarbonyl group, １－６ an alkylsulfonyl group, 12) C ３－１０ alicyclic sulfonyl group, 13) C ６－１０ 14) an arylsulfonyl group, 15) a 5- or 6-membered heteroarylsulfonyl group, or 16) an -OR ｃ１ (However, each of the substituents in 2) to 14) above may be substituted), wherein R ａ２ and R ｂ１may be joined together to form an optionally substituted 4- to 10-membered nitrogen-containing non-aryl heterocycle, R ｃ１ is 1) a hydrogen atom, 2) C １－６ an alkyl group; 3) C ３－１０ Alicyclic group, 4)C ６－１０ 5) aryl, 5) 5- or 6-membered heteroaryl, or 6) 4- to 10-membered non-aryl heterocycle (provided that each of the substituents in 2) to 6) above may be substituted), L １ represents a single bond, an oxygen atom, a sulfur atom, -SO-, -SO ２ -, -NR ｄ -, -NR ｄ C(=O)- or -NR ｄ SO ２ - and L ２ represents a single bond or an optionally substituted C １－６ an alkylene group, and Z is 1) a hydrogen atom, 2) a hydroxyl group, 3) a cyano group, 4) a carboxyl group, 5) C ３－１０ Alicyclic group, 6)C ６－１０ aryl, 7) 5- or 6-membered heteroaryl, 8) 4- to 10-membered non-aryl heterocycle, 9) C １－６ 10) an alkoxy group; ３－１０ 11) an alicyclic oxy group, ６－１０ 12) an aryloxy group, 13) a 4- to 10-membered non-aryl heterocyclic oxy group, 14) C １－６ Alkylthio group, 15) C ３－１０ alicyclic thio group, 16) C ６－１０ 17) an arylthio group, 18) a 4- to 10-membered non-aryl heterocyclic thio group (provided that each of the substituents in 5) to 18) above may be substituted). 19) —SO ２ -NR ｅ１ R ｆ１ , 20)-NR ｅ１ -C(=O)OR ｆ１ , 21)-NR ｇ１ -C(=O)NR ｅ１ R ｆ１ , 22)-NR ｅ１ -C(=S)Rｆ１ 、 23)-NR ｅ１ -C(=S)OR ｆ１ 、 24)-NR ｇ１ -C(=S)NR ｅ１ R ｆ１ 、 25)-NR ｇ１ -CR ｅ１ (=NR ｆ１ )、 26)-NR ｇ１ -CR ｅ１ (=N-OR ｆ１ )、 27)-NR ｈ１ -C(=NR ｇ１ )NR ｅ１ R ｆ１ 、 28)-NR ｈ１ -C(=N-OR ｇ１ )NR ｅ１ R ｆ１ 、 29)-NR ｉ１ -C(=NR ｈ１ )NR ｇ１ -NR ｅ１ R ｆ１ 、 30)-NR ｉ１ -C(=N-OR ｈ１ )NR ｇ１ -NR ｅ１ R ｆ１ 、 31)-NR ｅ１ -SO ２ -R ｆ１ 、 32)-NR ｇ１ -SO ２ -NR ｅ１ R ｆ１ 、 33)-C(=O)OR ｅ１ 、 34)-C(=S)OR ｅ１ 、 35)-C(=S)NR ｅ１ R ｆ１ 、 36)-C(=S)NR ｅ１ OR ｆ１ 、 37)-C(=S)NR ｇ１ -NR ｅ１ R ｆ１ 、 38)-C(=NR ｅ１ )R ｆ１ 、 39)-C(=N-OR ｅ１ )R ｆ１ 、 40)-C(=NR ｈ１ )NR ｇ１ -NR ｅ１ R ｆ１, 41)-C(=N-OR ｈ１ ) NR ｇ１ -NR ｅ１ R ｆ１ , 42)-NR ｅ１ R ｆ１ , 43)-NR ｇ１ -NR ｅ１ R ｆ１ , 44)-NR ｅ１ OR ｆ１ , 45)-NR ｅ１ -C(=O)R ｆ１ , 46)-C(=O)NR ｅ１ R ｆ１ , 47)-C(=O)NR ｅ１ OR ｆ１ , 48)-C(=O)NR ｇ１ -NR ｅ１ R ｆ１ , 49)-C(=O)R ｅ１ , 50)-C(=NR ｇ１ ) NR ｅ１ R ｆ１ , or 51)-C(=N-OR ｈ１ ) NR ｅ１ R ｆ１ R １ , R ２ and R ３ Any one of the following formula (2): [In formula (2), Y represents an oxygen atom, a sulfur atom, or —NR ｊ -, ring A is an optionally substituted 4- to 20-membered non-aryl heterocycle, L ３ is -C(=O)-, -S(=O)-, or -S(=O) ２ - and L ４ is 1) a single bond, 2) C １－６ an alkylene group; 3) C ３－１０ 4) a cycloalkylene group, ６－１０ arylene group 5) a 5- or 6-membered heteroarylene group, 6) a 4- to 10-membered non-aryl heterocyclylene group, or 7) —C(═N—OR ｈ１ )-(wherein each of the substituents 2) to 6) above may be substituted), R ５ is 1) a hydrogen atom, 2) C １－６an alkyl group; 3) C ３－１０ alicyclic group, 4) 4- to 10-membered non-aryl heterocycle, 5) C ６－１０ aryl, 6) 5- or 6-membered heteroaryl, 7) C １－６ an alkylthio group, or (provided that each of the substituents in 2) to 7) above may be substituted); 8) —NR ｅ１ OH, (R １ , R ２ and R ３ the remaining two are the same or different and independently represent a hydrogen atom, a halogen atom, an optionally substituted C １－６ alkyl group, optionally substituted C １－６ an alkoxy group, optionally substituted C １－６ an alkylthio group, an optionally substituted 5- or 6-membered heteroaryl, or —NR ａ３ R ｂ２ and R ｄ , R ｅ１ , R ｅ２ , R ｆ１ , R ｆ２ , R ｇ１ , R ｇ２ , R ｈ１ , R ｈ２ , R ｉ１ , R ｉ２ and R ｊ are each independently the same or different and represent a hydrogen atom, an optionally substituted C １－６ alkyl group, optionally substituted C ３－１０ Alicyclic group, optionally substituted C ６－１０ aryl, an optionally substituted 5- or 6-membered heteroaryl, or an optionally substituted 4- to 10-membered non-aryl heterocycle; R ｅ１ and R ｆ１ or R ｅ２ and R ｆ２ When the combination of R is bonded to the same nitrogen atom, they may be joined together to form an optionally substituted 4- to 10-membered nitrogen-containing non-aryl heterocycle, ４ 1) -C(=O)R ８ , 2)-SO ２ -L ６ -R８ (above 1) and 2) in the formula, R ８ is -NR ａ５ R ｂ４ , -NR ａ５ -L ７ -B(OR ｍ１ ) ２ , -OR ｍ１ or optionally substituted C １－６ is an alkyl group, and L ６ represents a single bond or -NR ａ６ -), 3) -NR ａ４ R ｂ３ , 4)-B(OR ｍ１ ) ２ , 5)-PO(OR ｍ１ ) (OR ｍ２ 6) an optionally substituted 5-membered heteroaryl, 7) an optionally substituted 5-membered non-aryl heterocycle, or 8) a bioisostere of any of 1) to 7) (provided that the formulae 2), 4), 5) and 6) above include carboxylic acid equivalents, and 8) may include these in duplicate), R ａ３ , R ａ４ , R ａ５ , R ａ６ , R ｂ２ , R ｂ３ and R ｂ４ are each independently the same or different and represent the R ａ１ , R ａ２ and R ｂ１ where R ａ３ and R ｂ２ , R ａ４ and R ｂ３ or R ａ５ and R ｂ４ When a combination of R is bonded to the same nitrogen atom, they may be joined together to form an optionally substituted 4- to 10-membered nitrogen-containing non-aryl heterocycle, ｍ１ is 1) a hydrogen atom, 2) C １－６ an alkyl group; 3) C ３－１０ Alicyclic group, 4)C ６－１０5) aryl, 5) 5- or 6-membered heteroaryl, or 6) 4- to 10-membered non-aryl heterocycle (provided that each of the substituents in 2) to 6) above may be substituted), provided that R ｍ１ is bonded to the boron atom via an oxygen atom, two R ｍ１ is C ２－４ The alkylene may be taken together with the boron atom and two oxygen atoms to form a 5- to 7-membered non-aryl heterocycle (the alkylene portion of the non-aryl heterocycle may be substituted), and R ｍ２ represents a hydrogen atom, an optionally substituted C １－６ an alkyl group or an optionally substituted C ３－１０ is an alicyclic group, ７ is an optionally substituted C １－３ It is an alkylene group.

[0079] In some embodiments, Z-L ２ -L １ is a hydrogen atom, optionally substituted C １－６ an alkyl group or an optionally substituted C １－６ In one embodiment, L is an alkylthio group. １ is a single bond.

[0080] In some embodiments, L ２ represents a single bond or an optionally substituted C １－６ In one embodiment, L is an alkylene group. ２ is a single bond.

[0081] In some embodiments, Z is 1) a hydrogen atom, 2) a hydroxyl group, 3) a cyano group, 4) a carboxyl group, 5) C ３－１０ Alicyclic group, 6)C ６－１０ aryl, 7) 5- or 6-membered heteroaryl, 8) 4- to 10-membered non-aryl heterocycle, 9) C １－６ 10) an alkoxy group; ３－１０ 11) an alicyclic oxy group, ６－１０ 12) an aryloxy group, 13) a 4- to 10-membered non-aryl heterocyclic oxy group, 14) C １－６Alkylthio group, 15) C ３－１０ alicyclic thio group, 16) C ６－１０ 17) an arylthio group, 18) a 4- to 10-membered non-aryl heterocyclic thio group (provided that each of the substituents in 5) to 18) above may be substituted). 19) —SO ２ -NR ｅ１ R ｆ１ , 20)-NR ｅ１ -C(=O)OR ｆ１ , 21)-NR ｇ１ -C(=O)NR ｅ１ R ｆ１ , 22)-NR ｅ１ -C(=S)R ｆ１ , 23)-NR ｅ１ -C(=S) OR ｆ１ , 24)-NR ｇ１ -C(=S)NR ｅ１ R ｆ１ , 25)-NR ｇ１ -CR ｅ１ (=NR ｆ１ ), 26)-NR ｇ１ -CR ｅ１ (=N-OR ｆ１ ), 27)-NR ｈ１ -C(=NR ｇ１ ) NR ｅ１ R ｆ１ , 28)-NR ｈ１ -C(=N-OR ｇ１ ) NR ｅ１ R ｆ１ , 29)-NR ｉ１ -C(=NR ｈ１ ) NR ｇ１ -NR ｅ１ R ｆ１ , 30)-NR ｉ１ -C(=N-OR ｈ１ ) NR ｇ１ -NR ｅ１ R ｆ１ , 31)-NR ｅ１ -SO ２ -R ｆ１ , 32)-NR ｇ１ -SO ２ -NR ｅ１ R ｆ１ , 33)-C(=O)OR ｅ１, 34)-C(=S)OR ｅ１ , 35)-C(=S)NR ｅ１ R ｆ１ , 36)-C(=S)NR ｅ１ OR ｆ１ , 37)-C(=S)NR ｇ１ -NR ｅ１ R ｆ１ , 38)-C(=NR ｅ１ ) R ｆ１ , 39)-C(=N-OR ｅ１ ) R ｆ１ , 40)-C(=NR ｈ１ ) NR ｇ１ -NR ｅ１ R ｆ１ , 41)-C(=N-OR ｈ１ ) NR ｇ１ -NR ｅ１ R ｆ１ , 42)-NR ｅ１ R ｆ１ , 43)-NR ｇ１ -NR ｅ１ R ｆ１ , 44)-NR ｅ１ OR ｆ１ , 45)-NR ｅ１ -C(=O)R ｆ１ , 46)-C(=O)NR ｅ１ R ｆ１ , 47)-C(=O)NR ｅ１ OR ｆ１ , 48)-C(=O)NR ｇ１ -NR ｅ１ R ｆ１ , 49)-C(=O)R ｅ１ , 50)-C(=NR ｇ１ ) NR ｅ１ R ｆ１ , or 51)-C(=N-OR ｈ１ ) NR ｅ１ R ｆ１ The R ｅ１ , R ｆ１ , R ｇ１ and R ｈ１is as defined herein. In a preferred embodiment, Z is any of 1), 2), 5) to 8), 39), or 42) above. In one embodiment, Z is a hydrogen atom. Alternatively, in another embodiment, Z is an optionally substituted C １－６ In yet another embodiment, Z is an optionally substituted C １－６ It is an alkyl group.

[0082] In a preferred embodiment, ZL ２ -L １ is a hydrogen atom. Alternatively, in another embodiment, Z-L ２ -L １ may be substituted C １－６ In yet another embodiment, Z-L is an alkylthio group. ２ -L １ may be substituted C １－６ It is an alkyl group.

[0083] In some embodiments, G is an oxygen atom, a sulfur atom, or —NR ａ１ In one embodiment, G is an oxygen atom or a sulfur atom. In a preferred embodiment, G is an oxygen atom. ａ１ is as defined herein.

[0084] In some embodiments, X is a hydroxyl group, an optionally substituted C １－６ an alkoxy group, or —NR ａ２ R ｂ１ In one embodiment, X is a hydroxyl group or an optionally substituted C １－６ In a preferred embodiment, X is a hydroxyl group. ａ２ and R ｂ１ is as defined herein.

[0085] In some embodiments, R １ , R ２ and R ３ Any one of the following formula (2): [In formula (2), Y represents an oxygen atom, a sulfur atom, or —NR ｊ-, ring A is an optionally substituted 4- to 20-membered non-aryl heterocycle, L ３ is -C(=O)-, -S(=O)-, or -S(=O) ２ - and L ４ is 1) a single bond, 2) C １－６ an alkylene group; 3) C ３－１０ 4) a cycloalkylene group, ６－１０ arylene group 5) a 5- or 6-membered heteroarylene group, 6) a 4- to 10-membered non-aryl heterocyclylene group, or 7) —C(═N—OR ｈ１ )-(wherein each of the substituents 2) to 6) above may be substituted), R ５ is 1) a hydrogen atom, 2) C １－６ an alkyl group; 3) C ３－１０ alicyclic group, 4) 4- to 10-membered non-aryl heterocycle, 5) C ６－１０ aryl, 6) 5- or 6-membered heteroaryl, 7) C １－６ an alkylthio group, or (provided that each of the substituents in 2) to 7) above may be substituted); 8) —NR ｅ１ OH, or １ , R ２ and R ３ the remaining two are the same or different and independently represent a hydrogen atom, a halogen atom, an optionally substituted C １－６ alkyl group, optionally substituted C １－６ an alkoxy group, optionally substituted C １－６ an alkylthio group, an optionally substituted 5- or 6-membered heteroaryl, or —NR ａ３ R ｂ２ where R ａ３ and R ｂ２ is as defined herein. In one preferred embodiment, R ３ has the structure of formula (2).

[0086] In one embodiment, R in formula (2) ５ 2) C １－６ alkyl group, 3) C ３－１０alicyclic group, 4) 4- to 10-membered non-aryl heterocycle, 5) C ６－１０ aryl, 6) 5- or 6-membered heteroaryl, or 7) C １－６ When the alkylthio group is an alkylthio group, the alkylthio group may be substituted with a carboxyl group. １－６ In one embodiment, 2), 3), 4), 5), 6), and 7) may be substituted with a carboxyl group. In one embodiment, 2), 3), 4), 5), 6), and 7) may be substituted with a C substituted with a carboxyl group. １－６ It may be substituted with an alkyl group.

[0087] In one embodiment, R １ , R ２ and R ３ When one of the formulas is expressed by formula (2), R １ , R ２ and R ３ The remaining two of R that do not have the structure of formula (2) are each independently selected from the group consisting of a hydrogen atom, a halogen atom, methyl, trifluoromethyl, methoxy, and trifluoromethoxy. ３ is expressed by formula (2), and R １ and R ２ are each independently selected from the group consisting of a hydrogen atom, a halogen atom, methyl, trifluoromethyl, methoxy, and trifluoromethoxy.

[0088] In some embodiments, Y is an oxygen atom, a sulfur atom, or —NR ｊ In one embodiment, Y is an oxygen atom or a sulfur atom. In a preferred embodiment, Y is an oxygen atom. ｊ is as defined herein.

[0089] In some embodiments, ring A is an optionally substituted 4- to 20-membered non-aryl heterocycle. In one embodiment, ring A is an optionally substituted 4- to 10-membered non-aryl heterocycle. In one embodiment, ring A is an optionally substituted 4- to 7-membered non-aryl heterocycle. In one embodiment, ring A is an optionally substituted 4- to 7-membered nitrogen-containing non-aryl heterocycle. In one embodiment, ring A is an optionally substituted 4- to 6-membered non-aryl heterocycle. In one embodiment, ring A is an optionally substituted 4- to 6-membered nitrogen-containing non-aryl heterocycle. In one embodiment, ring A is an optionally substituted azetidine ring. Within these embodiments, in certain particular embodiments, ring A is where R ６ represents a substituent on the azetidine ring, and R ６ａ The bond perpendicular to the wavy line indicates a bond with Y, and the bond marked with * indicates L ３ In one preferred embodiment, R ６ are each independently the same or different and are each independently selected from the group consisting of: 1) a hydrogen atom, 2) a halogen atom, 3) C １－６ 4) an alkyl group; １－６ and an alkoxy group (wherein each of the substituents in 3) and 4) above may be substituted with a halogen atom), and in a more preferred embodiment, the alkyl group is selected from the group consisting of 1) a hydrogen atom, 2) a halogen atom, and 3) a C alkyl group optionally substituted with a halogen atom. １－６ In certain embodiments, ring A is selected from the group consisting of: where m is 1, 2 or 3, n is 1, 2 or 3, m+n is 2, 3, 4 or 5, the bond perpendicular to the wavy line represents a bond to Y, and the bond marked with * represents a bond to L ３ In one embodiment, m+n is 2, 3, or 4. In one embodiment, m+n is 2 or 3. In a preferred embodiment, m+n is 2. In a more preferred embodiment, m=1 and n=1.

[0090] In some embodiments, L３ is -C(=O)-, -S(=O)-, or -S(=O) ２ In one embodiment, L ３ is -C(=O)- or -S(=O) ２ In a preferred embodiment, L ３ is —C(═O)—.

[0091] In some embodiments, L ４ is 1) a single bond, 2) C １－６ an alkylene group; 3) C ３－１０ 4) a cycloalkylene group, ６－１０ arylene group 5) a 5- or 6-membered heteroarylene group, 6) a 4- to 10-membered non-aryl heterocyclylene group, or 7) —C(═N—OR ｈ１ )-(wherein each of the substituents 2) to 6) above may be substituted). In one embodiment, L ４ is a single bond, -C(=N-OR ｈ１ )- or optionally substituted C １－６ an alkylene group, where R ｈ１ is optionally substituted C １－６ In one embodiment, it is a single bond or -NR ２１ R ２２ Or = NOR ２３ C optionally substituted with １－６ an alkylene group, where R ２１ , R ２２ and R ２３ are each independently a hydrogen atom, an optionally substituted C １－６ In a preferred embodiment, L is an alkyl group or an optionally substituted 4- to 10-membered non-aryl heterocyclic carbonyl group. ４ is a bond, -CH ２ -, -CH(NH ２ ) -, or -CH(NH ２ )-CH ２ -, where L ４ When an amino group is present in the ３ and combine.

[0092] In one embodiment, L ４ is a single bond, -CH ２ -, -CMe(NH ２ )-, -CH(NHMe)-, -CD(NH ２ )-(wherein D represents a deuterium atom), -CH(NH ２ ) - or -CH ２ CH ２ In one embodiment, L ４ is a single bond, -CH ２ -, or -CH(NH ２ )-.

[0093] In one embodiment, L ４ is 1)-(CH ２ ) ｐ -CR １０ (N.H.R. １１ ) -, 2) -(CH ２ ) ｑ -CR １２ R １３ -, or 3)-(CH ２ ) ｐ -CR １０ (N.H.R. １１ )-(CH ２ ) ｑ -CR １２ R １３ -, where p and q are independently 0 or 1, and R １０ is 1) a hydrogen atom, 2) a carboxyl group, or 3) -C(=O)NR １０ａ R １０ｂ and R １１ is 1) a hydrogen atom, 2) -C(=O)R １１ａ or 3) an optionally substituted 5- or 6-membered non-aryl heterocyclic carbonyl group, provided that R １０ -C(=O)NR １０ａ R １０ｂ When R １０ｂ and R １１ Let's get together -CH ２ CH ２ - may be formed, R １２ is 1) a hydrogen atom, or 2) an optionally substituted C １－４ is an alkyl group, R１３ is 1) a hydrogen atom, 2) a hydroxyl group, or 3) an optionally substituted C １－４ 4) an alkyl group, 5) a sulfanyl group, 6) an optionally substituted C １－４ an alkylthio group, 7) —NR １３ａ R １３ｂ , 8)-NR １３ａ -C(=O)R １３ｂ 9) an optionally substituted 5- or 6-membered non-aryl heterocyclic carbonylamino group; 10) —NR １３ａ -C(=O)NR １３ｂ R １３ｃ , 11)-C(=O)NR １３ａ R １３ｂ , 12)-C(=O)NR １３ａ OR １３ｂ , 13)-S(=O) ２ -R １３ａ , 14)-S(=O) ２ -NR １３ａ R １３ｂ , 15)-C(=O)NR １３ａ -S(=O) ２ -R １３ｂ or 16) -C(=O)NR １３ａ -S(=O) ２ -NR １３ｂ R １３ｃ and R １０ａ , R １０ｂ , R １１ａ , R １３ａ , R １３ｂ and R １３ｃ are each independently a hydrogen atom or an optionally substituted C １－４ It is an alkyl group.

[0094] In one embodiment, L ４ -CH(NH ２ )-CHR １３ -, and the NH ２ The carbon bonded to L ３ and R ５ is a hydrogen atom, and R １３ 1) -NH-C(=O)CH ３ , 2)-NH-C(=O)NH ２ , 3)-NH-C(=O)CH(NH２ )-CH ２ C(=O)NH ２ , 4)-NH-C(=O)CH ２ -NH ２ , 5)-NH-C(=O)CH(NH ２ )-CH ２ OH, or 6) a pyrrolidin-2-ylcarbonylamino group.

[0095] In one embodiment, L ４ -CH(NH ２ )-CR １２ R １３ -, and the NH ２ The carbon bonded to L ３ and R ５ is a hydrogen atom or methyl, R １２ is a hydrogen atom or methyl, R １３ is a benzylthio group or a sulfanyl group.

[0096] In one embodiment, L ４ -CH(NH ２ )-(CH ２ ) ｑ -CHR １３ -, q is 0 or 1, and the NH ２ The carbon bonded to L ３ and R ５ is a hydrogen atom, and R １３ is: 1) a carboxyl group, 2) -C(=O)NH ２ , 3)-C(=O)NH(CH ３ ), 4)-C(=O)N(CH ３ ) ２ , 5)-C(=O)NH-(CH ２ ) ２ -OH, 6) -C(=O)NH-(CH ２ ) ２ -NH ２ , 7)-C(=O)NH-S(=O) ２ -CH ３ , 8)-C(=O)NHOH, 9)-S(=O) ２ -NH ２ , 10)-S(=O) ２ -CH ３or 11) a hydroxyl group.

[0097] In one embodiment, L ４ -CH(NHR １１ )-CH ２ -, and the NHR １１ The carbon bonded to L ３ and R ５ is hydrogen, and R １１ 1) -C(=O)CH(NH ２ )-CH ２ C(=O)NH ２ , 2)-C(=O)CH ２ -NH ２ , 3)-C(=O)CH(CH ３ )-NH ２ , 4)-C(=O)CH(NH ２ )-CH ２ OH, or 5) pyrrolidin-2-ylcarbonyl.

[0098] In one embodiment, L ４ -CH(NHR １１ )-CH(COOH)-, and the NHR １１ The carbon bonded to L ３ and R ５ is hydrogen, and R １１ 1) -C(=O)CH(NH ２ )-CH ２ C(=O)NH ２ , 2)-C(=O)CH ２ -NH ２ , 3)-C(=O)CH(CH ３ )-NH ２ , 4)-C(=O)CH(NH ２ )-CH ２ OH, or 5) pyrrolidin-2-ylcarbonyl.

[0099] In one embodiment, L ４ Ha-CHR １３ - or -CH ２ -CHR １３ - and R ５ is hydrogen, and R １３ is -C(=O)NH ２ or —C(═O)NHOH.

[0100] In one embodiment, L ４ Ha-CH ２ -CR １０ (NH ２ )-, and the CH ２ The group is L ３ and R ５ is hydrogen, R １０ is a carboxy group or —C(═O)NH ２ is.

[0101] In one embodiment, L ４ Ha-(CH ２ ) ｐ -CR １０ (N.H.R. １１ )-(CH ２ ) ｑ -CHR １３ -or-CHR １３ - (CH ２ ) ｑ -CR １０ (N.H.R. １１ )-(CH ２ ) ｐ -, where q is 0 or 1, R ５ is hydrogen, (1) L ４ Ga-CHR １３ - (CH ２ ) ｑ -CR １０ (N.H.R. １１ )-(CH ２ ) ｐ When -, the -CHR １３ The carbon of the - group is L ３ p is 0, and R １０ represents a hydrogen atom, a carboxyl group, or —C(═O)NHR １０ｂ and R １１ is a hydrogen atom, and R １０ｂ is a hydrogen atom, provided that R １０ -C(=O)NHR １０ｂ When R １０ｂ and R １１ Let's get together -CH ２ CH ２ - may be formed, R １３is a hydrogen atom; (2) L ４ Ga-(CH ２ ) ｐ -CR １０ (N.H.R. １１ )-(CH ２ ) ｑ -CHR １３ -, the -(CH ２ ) ｐ The carbon of the - group is L ３ p is 1; R １０ and R １１ are both hydrogen atoms, and R １３ represents a carboxyl group or —C(═O)NR １３ａ R １３ｂ and R １３ａ and R １３ｂ are each independently a hydrogen atom or an optionally substituted C １－４ It is an alkyl group.

[0102] In one embodiment, L ４ is -CR １２ (NH ２ )- and R １２ is a hydrogen atom or a methyl group, R ５ is a C optionally substituted with one hydroxyl group １－４ It is an alkyl group.

[0103] In some embodiments, R ５ is 1) a hydrogen atom, 2) C １－６ an alkyl group; 3) C ３－１０ alicyclic group, 4) 4- to 10-membered non-aryl heterocycle, 5) C ６－１０ aryl, 6) 5- or 6-membered heteroaryl, 7) C １－６ an alkylthio group, or (provided that each of the substituents in 2) to 7) above may be substituted); 8) —NR ｅ１ OH, In one embodiment, R ５ represents a hydrogen atom, an optionally substituted C １－６ an alkyl group, an optionally substituted 4- to 10-membered non-aryl heterocycle, an optionally substituted C ６－１０Aryl, optionally substituted 5- or 6-membered heteroaryl, optionally substituted C １－６ an alkylthio group, or —NR ｅ１ OH, where R ｅ１ represents a hydrogen atom or an optionally substituted C １－６ In one embodiment, an optionally substituted 5- or 6-membered heteroaryl or an optionally substituted C ６－１０ It is aryl.

[0104] In one embodiment, R ５ is an optionally substituted 5- or 6-membered heteroaryl. In one embodiment, R ５ is an optionally substituted 4-10 membered non-aryl heterocycle. ５ represents a hydrogen atom or an optionally substituted C １－４ It is an alkyl group.

[0105] In one embodiment, R ５ is as follows: and the subscript d is selected from the group consisting of R ５ is the number of substitutable positions on the ring of each R ６ａ are independently: 1) a hydrogen atom, 2) a hydroxyl group, 3) a cyano group, 4) a nitro group, 5) a halogen, 6) C １－４ 7) an alkyl group, ３－１０ Alicyclic group, 8)C １－４ 9) an alkoxy group; ３－１０ 10) an alicyclic oxy group, ６－１０ 11) an aryloxy group, 12) a 4- to 10-membered non-aryl heterocyclic oxy group (provided that each of the substituents in 6) to 12) above may be substituted), 13) —SO ２ -NR ｅ２ R ｆ２ , 14)-NR ｇ２ -CR ｅ２ (=NR ｆ２ ), 15)-NR ｇ２ -CR ｅ２ (=N-OR ｆ２ ), 16)-NRｈ２ -C(=NR ｇ２ )NR ｅ２ R ｆ２ 、 17)-NR ｈ２ -C(=N-OR ｇ２ )NR ｅ２ R ｆ２ 、 18)-NR ｉ２ -C(=NR ｈ２ )NR ｇ２ -NR ｅ２ R ｆ２ 、 19)-NR ｉ２ -C(=N-OR ｈ２ )NR ｇ２ -NR ｅ２ R ｆ２ 、 20)-C(=NR ｅ２ )R ｆ２ 、 21)-C(=N-OR ｅ２ )R ｆ２ 、 22)-C(=NR ｈ２ )-NR ｅ２ R ｆ２ 、 23)-C(=NR ｈ２ )NR ｇ２ -NR ｅ２ R ｆ２ 、 24)-C(=N-OR ｈ２ )NR ｇ２ -NR ｅ２ R ｆ２ 、 25)-NR ｅ２ R ｆ２ 、 26)-NR ｇ２ -NR ｅ２ R ｆ２ 、 27)-NR ｅ２ OR ｆ２ 、 28)-NR ｅ２ -C(=O)R ｆ２ 、 29)-C(=O)NR ｅ２ R ｆ２ 、 30)-C(=O)NR ｅ２ OR ｆ２ 、 31)-C(=O)NR ｇ２ -NR ｅ２ R ｆ２ 、 32)-C(=O)R ｅ２ 、 33)-C(=O)OR ｅ２ 、および 34)-C(=N-OR ｈ２ )NR ｅ２ R ｆ２and each R is selected from the group consisting of ６ｂ are independently: 1) a hydrogen atom; 2) a hydroxyl group; 3) C １－４ an alkyl group (wherein the alkyl group may be substituted); 4) C ３－１０ an alicyclic group, (however, the alicyclic group may be substituted); 5) —C(═NR ｅ２ ) R ｆ２ , 6)-C(=N-OR ｅ２ ) R ｆ２ , 7)-SO ２ -NR ｅ２ R ｆ２ , 8)-C(=NR ｈ２ )-NR ｅ２ R ｆ２ , 9)-C(=NR ｈ２ ) NR ｇ２ -NR ｅ２ R ｆ２ , 10)-C(=N-OR ｈ２ ) NR ｇ２ -NR ｅ２ R ｆ２ , 11)-C(=O)NR ｅ２ R ｆ２ , 12)-C(=O)NR ｅ２ OR ｆ２ , 13)-C(=O)NR ｇ２ -NR ｅ２ R ｆ２ , 14)-C(=O)R ｅ２ , and 15)-C(=N-OR ｈ２ ) NR ｅ２ R ｆ２ is selected from the group consisting of:

[0106] In one embodiment, R ５ is as follows: and the subscript d is a 5- or 6-membered aryl or heteroaryl selected from the group consisting of R ５ is the number of substitutable positions on the ring of each R ６ａ are independently: 1) a hydrogen atom, 2) a hydroxyl group, 3) a halogen, 4) C １－４ an alkyl group, wherein the alkyl group is NR ｅ２ R ｆ２ , a 5- or 6-membered non-aryl heterocycle, —C(═O)ORｆ２ or may be substituted with a hydroxyl group) 5) C １－４ Alkoxy group 6) -NR ｅ２ R ｆ２ , and 7) —C(═O)OR ｅ２ and each R is selected from the group consisting of ６ｂ are independently: 1) a hydrogen atom, 2) a hydroxyl group, and 3) C １－４ an alkyl group, wherein the alkyl group is NR ｅ２ R ｆ２ , —C(═O)NR ｅ２ R ｆ２ , -C(=O)OR ｆ２ or hydroxyl groups).

[0107] In one embodiment, R ｅ２ and R ｆ２ are each independently the same or different and represent a hydrogen atom, an optionally substituted C １－６ an alkyl group or an optionally substituted C ３－１０ In one embodiment, R ｅ２ and R ｆ２ are each independently the same or different and represent a hydrogen atom or an optionally substituted C １－６ In one embodiment, R ｅ２ and R ｆ２ is a hydrogen atom. ６ａ is -NR ｅ２ R ｆ２ and R ｅ２ and R ｆ２ is a hydrogen atom on one side and a C atom on the other side. １－４ an alkyl group (which may be substituted with an amino group or a hydroxyl group);

[0108] In one embodiment, each R ６ａ may independently be halogen.

[0109] In one embodiment, each R ６ａ may independently be an alkylamino group substituted with an amino group. ６ａ is independent, NR ｅ２ Rｆ２ where R ｅ２ is C １－６ is an alkyl group, １－６ The alkyl group is —NR １０ａ R １１ａ and R １０ａ and R １１ａ are each independently defined as described in the specification.

[0110] In one embodiment, each R ６ａ may independently be —C(═O)OH.

[0111] In one embodiment, each R ６ａ and / or each R ６ｂ may independently be an alkyl group substituted with a carboxyl group. ６ａ and / or each R ６ｂ are independently C substituted with a —C(═O)OH group. １－４ It may be an alkyl group.

[0112] In one embodiment, R ５ is as follows: and the subscript d is a 4-6 membered non-aryl heterocycle selected from the group consisting of R ５ is the number of substitutable positions on the ring of each R ７ａ are independently: 1) a hydrogen atom, 2) a hydroxyl group, 3) a cyano group, 4) a halogen, 5) C １－４ 6) an alkyl group, ３－１０ Alicyclic group, 7)C １－４ an alkoxy group, 8) C ３－１０ 9) an alicyclic oxy group, C ６－１０ 10) an aryloxy group, 11) a 4- to 10-membered non-aryl heterocyclic oxy group, (provided that each of the substituents in 5) to 11) above may be substituted). 12) —SO ２ -NR ｅ３ R ｆ３ , 13)-NR ｇ２ -CR ｅ３ (=NR ｆ３ ), 14)-NR ｇ２ -CR ｅ３ (=N-ORｆ３ )、 15)-NR ｈ２ -C(=NR ｇ２ )NR ｅ３ R ｆ３ 、 16)-NR ｈ２ -C(=N-OR ｇ２ )NR ｅ３ R ｆ３ 、 17)-NR ｉ２ -C(=NR ｈ２ )NR ｇ２ -NR ｅ３ R ｆ３ 、 18)-NR ｉ２ -C(=N-OR ｈ２ )NR ｇ２ -NR ｅ３ R ｆ３ 、 19)-C(=NR ｅ３ )R ｆ３ 、 20)-C(=N-OR ｅ３ )R ｆ３ 、 21)-C(=NR ｈ２ )-NR ｅ３ R ｆ３ 、 22)-C(=NR ｈ２ )NR ｇ２ -NR ｅ３ R ｆ３ 、 23)-C(=N-OR ｈ２ )NR ｇ２ -NR ｅ３ R ｆ３ 、 24)-NR ｅ３ R ｆ３ 、 25)-NR ｇ２ -NR ｅ３ R ｆ３ 、 26)-NR ｅ３ OR ｆ３ 、 27)-NR ｅ３ -C(=O)R ｆ３ 、 28)-C(=O)NR ｅ３ R ｆ３ 、 29)-C(=O)NR ｅ３ OR ｆ３ 、 30)-C(=O)NR ｇ２ -NR ｅ３ R ｆ３ 、 31)-C(=O)R ｅ３ 、 32)-C(=O)OR ｅ３ 、および 33)-C(=N-OR ｈ２ )NR ｅ３R ｆ３ and each R is selected from the group consisting of ７ｂ are independently: 1) a hydrogen atom; 2) a hydroxyl group; 3) C １－４ an alkyl group (wherein the alkyl group may be substituted); 4) C ３－１０ an alicyclic group, (however, the alicyclic group may be substituted); 5) —C(═NR ｅ３ ) R ｆ３ , 6)-C(=N-OR ｅ３ ) R ｆ３ , 7)-SO ２ -NR ｅ３ R ｆ３ , 8)-C(=NR ｈ２ )-NR ｅ３ R ｆ３ , 9)-C(=NR ｈ２ ) NR ｇ２ -NR ｅ３ R ｆ３ , 10)-C(=N-OR ｈ２ ) NR ｇ２ -NR ｅ３ R ｆ３ , 11)-C(=O)NR ｅ３ R ｆ３ , 12)-C(=O)NR ｅ３ OR ｆ３ , 13)-C(=O)NR ｇ２ -NR ｅ３ R ｆ３ , 14)-C(=O)R ｅ３ , and 15)-C(=N-OR ｈ２ ) NR ｅ３ R ｆ３ R is selected from the group consisting of ｅ３ and R ｆ３ is R described in Section B1 ｅ２ and R ｆ２ is synonymous with.

[0113] In one embodiment, R ５ is as follows: and the subscript d is a 4-6 membered non-aryl heterocycle selected from the group consisting of R ５ is the number of substitutable positions on the ring of each R ７ａ are independently: 1) a hydrogen atom, 2) a hydroxyl group, 3) a halogen, 4) C １－４an alkyl group, wherein the alkyl group is NR ｅ３ R ｆ３ , a 5- or 6-membered non-aryl heterocycle, —C(═O)OR ｆ３ or may be substituted with a hydroxyl group) 5) C １－４ Alkoxy group 6) -NR ｅ３ R ｆ３ , 7)-C(=O)OR ｅ３ , and 8) C ６－１０ Aryl 9) —C(═O)NR ｅ３ R ｆ３ and each R is selected from the group consisting of ７ｂ are independently: 1) a hydrogen atom, 2) a hydroxyl group, and 3) C １－４ an alkyl group, wherein the alkyl group is NR ｅ３ R ｆ３ , -C(=O)OR ｆ３ or a hydroxyl group), and R ｅ３ and R ｆ３ is R according to any one of items B38 to B40. ｅ２ and R ｆ２ is synonymous with.

[0114] In some embodiments, R １ , R ２ and R ３ When any one of the groups is represented by formula (2), the remaining two groups are each independently the same or different and represent a hydrogen atom, a halogen atom, an optionally substituted C １－６ alkyl group, optionally substituted C １－６ an alkoxy group, optionally substituted C １－６ an alkylthio group, an optionally substituted 5- or 6-membered heteroaryl, or —NR ａ３ R ｂ２ where R ａ３ and R ｂ２ is as described herein. In one preferred embodiment, R ３ is expressed by equation (2).

[0115] R ３ In one embodiment, R １ and R ２are each independently the same or different and are each independently selected from the group consisting of: 1) a hydrogen atom, 2) a halogen atom, 3) C １－６ 4) an alkyl group; １－６ an alkoxy group, and 5) C １－６ alkylthio groups (wherein each of the substituents 3) to 5) above may be substituted).

[0116] In this embodiment, R １ and R ２ are each independently the same or different and are each independently selected from the group consisting of 1) a hydrogen atom, 2) a halogen atom, and 3) an optionally substituted C １－６ In a preferred embodiment, R １ and R ２ are both hydrogen atoms.

[0117] In some embodiments, R of formula (1a) and (1b) ４ 1) -C(=O)R ８ , 2)-SO ２ -L ６ -R ８ (above 1) and 2) in the formula, R ８ is -NR ａ５ R ｂ４ , -NR ａ５ -L ７ -B(OR ｍ１ ) ２ , -OR ｍ１ or optionally substituted C １－６ is an alkyl group, and L ６ represents a single bond or -NR ａ６ -), 3) -NR ａ４ R ｂ３ , 4)-B(OR ｍ１ ) ２ , 5)-PO(OR ｍ１ ) (OR ｍ２ 6) an optionally substituted 5-membered heteroaryl, 7) an optionally substituted 5-membered non-aryl heterocycle, or 8) a bioisostere of any of 1) to 7) (provided that the formulas 2), 4), 5) and 6) above include carboxylic acid equivalents, and 8) may include these in duplicate). In one embodiment, R４ is -C(=O)-OR ｍ１ or its carboxylic acid equivalent. In a preferred embodiment, R ４ is 1) —COOH (i.e., a carboxyl group), or 2) a carboxylic acid equivalent. ａ４ , R ａ５ , R ａ６ , R ｂ３ , R ｂ４ , L ７ , R ｍ１ and R ｍ２ is as defined herein.

[0118] A specific embodiment of the compound of the present invention is specifically represented by the following formula (3a) or (3b): In formula (3a) or (3b), X, R １ , R ２ and R ３ is as defined herein, and R ４ is 1)-COOR ｍ１ (where R ｍ１ is a hydrogen atom, C １－６ Alkyl group, C ３－１０ Alicyclic group, C ６－１０ aryl, 5- or 6-membered heteroaryl, or 4- to 10-membered non-aryl heterocycle, wherein said C １－６ Alkyl group, ３－１０ alicyclic group, said C ６－１０ aryl, the 5- or 6-membered heteroaryl, and the 4- to 10-membered non-aryl heterocycle, each of which may be optionally substituted; and 2) a bioisostere of 1). ４ is 1) —COOH (i.e., a carboxyl group), or 2) a carboxylic acid equivalent.

[0119] Preferred embodiments of the compound of the present invention are specifically represented by the following formulae (4a) and (4b): In formula (4a) and (4b), X, R ４ , Y, Ring A, L ３ , L４ , and R ５ is as defined herein, and R １ and R ２ are each independently the same or different and represent a hydrogen atom, a halogen atom, or C １－６ Alkyl group, C １－６ Alkoxy group (provided that the C １－６ Alkyl group and C １－６ The alkoxy group may be substituted with 1 to 5 halogen atoms.

[0120] More preferred embodiments of the compound of the present invention are specifically represented by the following formulae (5a) and (5b): In formula (5a) and (5b), R １ , R ２ , Y., L. ３ , L ４ , R ５ and ring A are as defined herein, and ring A is an optionally substituted 4- to 6-membered nitrogen-containing non-aryl heterocycle.

[0121] More preferred embodiments of the compound of the present invention are specifically represented by the following formulae (6a) and (6b): In formulas (6a) and (6b), L is a compound represented by the formula: ３ , L ４ , and R ５ is as defined herein, m is an integer of 1, 2, or 3, n is an integer of 1, 2, or 3, and m+n is 2, 3, or 4. In one embodiment, m is 1 or 2, n is 1 or 2, and m+n is 2 or 3. In a preferred embodiment, m is 1 and n is 1.

[0122] Specific examples of preferred embodiments of the compound of the present invention are shown below: or a pharmaceutically acceptable salt thereof, ＺＬ is a substituent selected from the group consisting of Z1 to Z4 below, and R １ , R ２ , R３ But one of them is and the remaining two are hydrogen atoms, and the linking group L ａ is a substituent selected from the group consisting of L1 to L36 below, and the substituent Q ａ is a substituent selected from the group consisting of Q1 to Q103 below, or a pharmaceutically acceptable salt thereof. ＺＬ : Linking group L ａ : Substituent Q ａ :

[0123] More preferred embodiments of the compound of the present invention can be specifically exemplified as compounds of the following formula: or a pharmaceutically acceptable salt thereof, ＺＬ is a substituent selected from the group consisting of Z1 to Z4, and R １ and R ２ is a hydrogen atom, and R ３ but, and the linking group L ａ is a substituent selected from the group consisting of L1 to L36, and the substituent Q ａ is a substituent selected from the group consisting of Q1 to Q103 above, or a pharmaceutically acceptable salt thereof.

[0124] More preferred embodiments of the compound of the present invention can be exemplified by the compounds shown in the following Table (1) or pharmaceutically acceptable salts thereof.

[0125] Another embodiment of the compound of the present invention is specifically represented by the following formula (11): In formula (11), Z, L and L are each independently substituted or unsubstituted, and the substituted or unsubstituted alkyl groups are each independently substituted or unsubstituted. １ , L２ , X, R １ , R ２ , R ３ , and R ４ is as defined herein, and R Ｇ is a hydroxyl group, a thiol group, or -NHR ａ１ and R ａ１ is as defined herein.

[0126] Another embodiment of the compound of the present invention is specifically represented by the following formula (12): In formula (12), X, R １ , R ２ , R ３ , and R ４ is as defined herein, and R Ｇ is a hydroxyl group, a thiol group, or -NHR ａ１ and R ａ１ is as defined herein. The compound of formula (12) and the compound of formula (1a) or (3a) can be mutually convertible by an equilibrium reaction in an aqueous solution or in a living body, and can be bioequivalents.

[0127] Another embodiment of the compound of the present invention is specifically represented by the following formula (13): In formula (13), X, Y, ring A, L, and the like are each independently selected from the group consisting of methyl, ... ３ , L ４ , R １ , R ２ , R ４ , and R ５ is as defined herein, and R Ｇ is a hydroxyl group, a thiol group, or -NHR ａ１ and R ａ１ is as defined herein.

[0128] A preferred embodiment of the compound of the present invention is specifically represented by the following formula (14): In formula (14), X, L and L are each independently a substituted or unsubstituted alkyl group, and the substituted or unsubstituted alkyl group is also a substituted or unsubstituted alkyl group. ３ , L ４ , m, n, and R ５is as defined herein, and R Ｇ is a hydroxyl group, a thiol group, or -NHR ａ１ and R ａ１ is as defined herein.

[0129] The compounds of the present invention are further described below. Depending on the type of substituent, the compounds of the present invention may exist as stereoisomers such as tautomers and geometric isomers, and optical isomers, and these are also included in the present invention. That is, when the compounds of the present invention have one or more asymmetric carbon atoms, diastereomers and optical isomers exist, and mixtures and isolated forms of these diastereomers and optical isomers are also included in the compounds of the present invention.

[0130] Furthermore, the compound of the present invention may exist in a structure represented by the following formula (11) due to an equilibrium state or the like depending on environmental conditions such as temperature and humidity, or physical factors such as whether the compound is in a solid, liquid, or solution, and such structures are also included in the compound of the present invention. In formula (11), X represents a hydroxyl group, a thiol group, or —NHR ａ１ represents Z, L １ , L ２ , R Ｇ , R １ , R ２ , R ３ , R ４ , and R ａ１ has the same definition as described herein, and formula (1a) has the same definition as described herein.

[0131] For example, the structure of the compounds of the examples of the present invention can be determined by proton nuclear magnetic resonance spectroscopy ( １ The above-mentioned structures are based on estimates that are considered to be most reasonable by a person skilled in the art, obtained by using techniques such as H-NMR, liquid chromatography mass spectrometry (LCMS), etc., but are merely structural estimates under specific individual measurement environments. In particular, the structure of formula (1a), the structure of formula (1b), and the structure of formula (11) may be mutually converted or partially converted into one of the structures and mixed, depending on the properties inherent to each compound, various environmental conditions such as temperature and humidity, or physical factors such as being in a solid, liquid, or solution.

[0132] The compounds of the present invention also include various hydrates, solvates and crystalline polymorphs.

[0133] Additionally, the compounds of the present invention may contain isotopes, e.g., ２ H (or D), ３ H (or T), １１ C. １３ C. １４ C. １３ N. １５ N. １５ O. ３５ S. １８ F. １２５ I, etc.), and these compounds are also included in the compounds of the present invention.

[0134] Furthermore, the scope of the present invention also includes prodrugs of the compounds of the present invention. In the present invention, a prodrug refers to a derivative that is hydrolyzed by acid or enzymatic decomposition in vivo to give a compound of formula (1a), (1b), or (11). For example, when the compound of formula (1a), (1b), or (11) has a hydroxyl group, an amino group, or a carboxyl group, these groups can be modified in a conventional manner to produce a prodrug.

[0135] For example, in the case of a compound having a carboxyl group, the carboxyl group may be replaced by an alkoxycarbonyl group, an alkylthiocarbonyl group, or an alkylaminocarbonyl group.

[0136] Furthermore, for example, in the case of a compound having an amino group, examples include a compound in which the amino group is substituted with an alkanoyl group to become an alkanoylamino group, a compound in which the amino group is substituted with an alkoxycarbonyl group to become an alkoxycarbonylamino group, a compound in which the amino group is substituted with an alkoxycarbonylamino group, a compound in which the amino group is substituted with an alkanoyloxymethylamino group, or a compound in which the amino group is hydroxylamine.

[0137] Further, for example, in the case of a compound having a hydroxyl group, examples include a compound in which the hydroxyl group is substituted with the above-mentioned alkanoyl group to form an alkanoyloxy group, a compound which is a phosphate ester, or a compound which is an alkanoyloxymethyloxy group.

[0138] The alkyl moiety of the group used for making these prodrugs includes the above-mentioned alkyl groups, and the alkyl group may be substituted with, for example, an alkoxy group, etc. Preferred examples include the following:

[0139] For example, examples of the compound in which a carboxyl group is an alkoxycarbonyl group include alkoxycarbonyl such as methoxycarbonyl or ethoxycarbonyl, or alkoxycarbonyl substituted with an alkoxy group such as methoxymethoxycarbonyl, ethoxymethoxycarbonyl, 2-methoxyethoxycarbonyl, 2-methoxyethoxymethoxycarbonyl or pivaloyloxymethoxycarbonyl.

[0140] In the present invention, "pharmaceutically acceptable salt" refers to an acid addition salt and a base addition salt that are pharmaceutically acceptable. Examples of "pharmaceutically acceptable salt" include, but are not limited to, acetate, propionate, butyrate, formate, trifluoroacetate, maleate, fumarate, tartrate, citrate, stearate, succinate, ethylsuccinate, malonate, lactobionate, gluconate, glucoheptonate, benzoate, methanesulfonate, benzenesulfonate, paratoluenesulfonate (tosylate), lauryl sulfate, malate, ascorbate, mandelate, saccharinate, Examples of the acid addition salts include xinafoate, pamoate, cinnamate, adipate, cysteine ​​salt, N-acetylcysteine ​​salt, hydrochloride, hydrobromide, phosphate, sulfate, hydroiodide, nicotinate, oxalate, picrate, thiocyanate, undecanoate, acrylic acid polymer salt, and carboxyvinyl polymer salt; inorganic base addition salts such as lithium salt, sodium salt, potassium salt, and calcium salt; organic base addition salts such as morpholine and piperidine; and addition salts with amino acids such as aspartic acid and glutamic acid.

[0141] The compound of the present invention can be administered orally or parenterally, either directly or in the form of a formulation, medicament, or pharmaceutical composition using an appropriate dosage form. Specific examples of these dosage forms include, but are not limited to, tablets, capsules, powders, granules, liquids, suspensions, injections, patches, and poultices. These formulations can be produced by known methods using additives commonly used as pharmaceutical additives.

[0142] These additives may include, depending on the purpose, excipients, disintegrants, binders, fluidizing agents, lubricants, coating agents, solubilizers, solubilizers, thickeners, dispersants, stabilizers, sweeteners, flavors, etc. Specific examples of these additives include, but are not limited to, lactose, mannitol, crystalline cellulose, low-substituted hydroxypropyl cellulose, corn starch, partially pregelatinized starch, carmellose calcium, croscarmellose sodium, hydroxypropyl cellulose, hydroxypropyl methylcellulose, polyvinyl alcohol, magnesium stearate, sodium stearyl fumarate, polyethylene glycol, propylene glycol, titanium oxide, talc, etc.

[0143] The dose of the compound of the present invention is appropriately selected depending on the animal to be administered, the administration route, the disease, the age, weight, and symptoms of the patient. For example, in the case of oral administration, the lower limit is 0.01 mg (preferably 100 mg) and the upper limit is 10,000 mg (preferably 6,000 mg) per day for an adult, and this amount can be administered once a day or in divided doses.

[0144] The compounds of the present invention have inhibitory activity against β-lactamase. Therefore, when used in combination with an antibacterial agent, they can serve as a useful agent for the prevention or treatment of bacterial infections. Specific examples of such bacterial infections include sepsis, febrile neutropenia, bacterial meningitis, bacterial endocarditis, otitis media, sinusitis, pneumonia, lung abscess, empyema, secondary infections of chronic respiratory lesions, pharyngitis / laryngitis, tonsillitis, osteomyelitis, arthritis, peritonitis, intraperitoneal abscess, cholecystitis, cholangitis, liver abscess, deep skin infections, lymphangitis / lymphadenitis, secondary infections of trauma / burns, surgical wounds, and the like, urinary tract infections, genital infections, eye infections, and dental infections.

[0145] The compounds of the present invention can be used in combination with at least one or more agents selected from antibacterial, antifungal, antiviral, anti-inflammatory or antiallergic agents to treat one or more bacterial infections described herein.Preferably, antibacterial agents are used, and more preferably β-lactam drugs, specifically amoxicillin, ampicillin (pivanpicillin, hetacillin, bacampicillin, metampicillin, talampicillin), epicillin, carbenicillin (carindacillin), ticarcillin, temocillin, azlocillin, piperacillin, mezlocillin, mecillinam (pivmecillinam), sulbenicillin, benzylpenicillin (G), clometocillin, benzathine benzylpenicillin, procaine benzylpenicillin, azidocillin, penamicillin Cirrhosis, phenoxymethylpenicillin (V), propicillin, benzathine phenoxymethylpenicillin, phenethicillin, cloxacillin (dicloxacillin, flucloxacillin), oxacillin, methicillin, nafcillin, faropenem, biapenem, doripenem, ertapenem, imipenem, meropenem, panipenem, tomopenem, razupenem, cefazolin, cephacetrile, cefadroxil, cephalexin, cephaloglycin, cephalonium, cephaloridine, cephalothin, cephapirin, cefatrizine , cefazedone, cefazaflur, cephradine, cefroxadine, ceftezole, cefaclor, cefamandole, cefminox, cefonicid, ceforanide, cefotiam, cefprozil, cefbuperazone, cefuroxime, cefuzonam, cefoxitin, cefotetan, cefmetazole, loracarbef, cefixime, ceftazidime, ceftriaxone, cefcapene, cefdaloxime, cefdinir, cefditoren, cefetamet, cefmenoxime, cefodizime, cefoperazone, cefotaxime, cefpimizole, cef pyramide, cefpodoxime, cefsulodin, cefteram, ceftibuten, ceftiolene, ceftizoxime, flomoxef, latamoxef, cefepime, cefozopran, cefpirome, cefquinome, ceftobiprole, ceftaroline, CXA-101, RWJ-54428, MC-04546, ME1036, BAL30072, SYN2416, ceftiofur, cefquinome, cefovecin, aztreonam, tigenonam, carumonam, RWJ-442831, RWJ-333441, or RWJ-333442.The administration timing of the compound of the present invention and the therapeutic agent thereof is not limited, and they may be administered to the subject simultaneously or at different times. The compound of the present invention and the therapeutic agent thereof may also be used as a combined preparation. The dosage of the therapeutic agent may be appropriately selected based on the clinically used dose. The compounding ratio of the compound of the present invention and the therapeutic agent thereof may be appropriately selected depending on the subject, administration route, target disease, symptoms, combination, etc.

[0146] In another embodiment of the present invention, when a pharmaceutical composition containing an antibacterial agent such as a β-lactam agent is used, the compound of the present invention can be administered simultaneously or at different times in combination. Such pharmaceutical compositions containing a β-lactam agent are also within the scope of the present invention and can be used for the treatment or prevention of bacterial infections such as sepsis, febrile neutropenia, bacterial meningitis, bacterial endocarditis, otitis media, sinusitis, pneumonia, lung abscess, empyema, secondary infections of chronic respiratory lesions, pharyngitis / laryngitis, tonsillitis, osteomyelitis, arthritis, peritonitis, intraperitoneal abscess, cholecystitis, cholangitis, liver abscess, deep skin infections, lymphangitis / lymphadenitis, secondary infections of trauma / burns and surgical wounds, and urinary tract infections, genital infections, eye infections, and dental infections.

[0147] Such medicaments, formulations, and pharmaceutical compositions can be produced by mixing the compound of the present invention and / or an additional drug (e.g., an antibacterial agent such as a β-lactam drug) with any appropriate ingredient, together or separately, as a combination drug or as separate drugs, using any technique known in the art, and can be formulated into an appropriate formulation, for example, a tablet, capsule, powder, granule, liquid, suspension, injection, patch, or cataplasm, using any technique known in the art. When the compound of the present invention and / or an additional drug (e.g., an antibacterial agent such as a β-lactam drug) are prepared as separate drugs, they may be provided as a kit of two drugs, or one component may be provided as a single drug, along with instructions (such as a package insert) instructing that the other component (the additional drug (e.g., an antibacterial agent such as a β-lactam drug in the case of the compound of the present invention, or the compound of the present invention in the case of the additional drug (e.g., an antibacterial agent such as a β-lactam drug)) be administered in combination, simultaneously or at different times.

[0148] When the compound of the present invention is used as an active ingredient of a medicine, it is not intended to be used only in humans, but can also be used in other animals other than humans (cats, dogs, cows, chickens, fish, etc.).

[0149] The production methods of the compounds of the present invention will be explained below with reference to examples, but the present invention is not limited to these.

[0150] The compounds of the present invention can be produced by, for example, the production methods described below, but are not limited to these. These production methods can be appropriately improved based on the knowledge of those skilled in organic synthetic chemistry. In the production methods below, the compounds used as raw materials may be used in the form of salts, as long as they do not interfere with the reaction.

[0151] In the following production methods, even if the use of a protecting group is not specifically specified, if any functional group other than the reactive site changes under the reaction conditions or if it is not suitable for post-reaction treatment, the target compound can be obtained by protecting the site other than the reactive site as necessary and deprotecting it after the reaction or a series of reactions. The protecting groups used in these processes are listed in the literature (TW Greene and PGM Wuts, "Protective Groups in Organic Synthesis", 3 rd Ed., John Wiley and Sons, Inc., New York (1999)) can be used. Introduction and removal of the protecting group can be carried out by a method commonly used in organic synthetic chemistry (for example, the method described in the above-mentioned literature) or a method based thereon.

[0152] The starting materials and intermediates in the following production methods are commercially available or can be obtained by synthesis from known compounds according to known methods or methods described in known literature. Furthermore, salts of these starting materials and intermediates may be used as long as they do not interfere with the reaction.

[0153] The intermediates and target compounds in the following production methods can be converted into other compounds included in the present invention by appropriately converting their functional groups. The conversion of functional groups in this case can be carried out by a method commonly used in organic synthetic chemistry (for example, RC Larock, "Comprehensive Organic Transformations", 2 nd Ed., John Wiley and Sons, Inc., New York (1999), or a method similar thereto.

[0154] In the following production methods, an inert solvent means a solvent that does not react with the raw materials, reagents, bases, acids, catalysts, ligands, etc. used in the reaction (hereinafter, sometimes referred to as "raw materials, etc. used in the reaction"). Even if the solvent used in each step reacts with the raw materials, etc. used in the reaction, it can be used as an inert solvent as long as the target reaction proceeds and the target compound is obtained.

[0155] Production Method 1 Among the compounds of formula (1a), the compound represented by the following formula (1-7) can be produced, for example, by the following production method. (In the formula, L １ , L ２ , Y, Z, Ring A, L ３ , L ４ , G.R. １ , R ２ , R ４ , R ５ is as defined in item 1, and X ａ is a hydroxyl group or C １－６ an alkoxy group, H is a hydrogen atom, LG is a leaving group (for example, a halogen atom such as chlorine, bromine, or iodine, a lower alkylsulfonyloxy group such as methanesulfonyloxy, a trihalogenomethanesulfonyloxy group such as trifluoromethanesulfonyloxy, or an arylsulfonyloxy group such as benzenesulfonyloxy or p-toluenesulfonyloxy), T is a hydroxyl group or a leaving group (for example, a halogen atom such as chlorine, bromine, or iodine, a lower alkylsulfonyloxy group such as methanesulfonyloxy, a trihalogenomethanesulfonyloxy group such as trifluoromethanesulfonyloxy, or an arylsulfonyloxy group such as benzenesulfonyloxy or p-toluenesulfonyloxy), PG １ represents a protecting group for a hydroxyl group (for example, a tert-butoxycarbonyl group, an acetyl group, a methoxymethyl group, a p-methoxybenzyl group, a tert-butyldimethylsilyl group, a trimethylsilyl group, etc.), PG ２ and P.G. ３ is a protecting group for a boronic acid (e.g., an optionally substituted C １－６an alkyl group, or a structure represented by the following formula: PG ４ represents a hydrogen atom, a protective group for a hydroxyl group (for example, a tert-butoxycarbonyl group, an acetyl group, a methoxymethyl group, a p-methoxybenzyl group, a tert-butyldimethylsilyl group, a trimethylsilyl group, etc.), a protective group for a thiol group (for example, an acetamidomethyl group or a trityl group), or a protective group for an amino group (for example, an ethoxycarbonyl group, a tert-butoxycarbonyl group, an acetyl group, a benzoyl group, a trifluoroacetyl group, a benzyloxycarbonyl group, a 3- or 4-chlorobenzyloxycarbonyl group, a triphenylmethyl group, a methanesulfonyl group, a p-toluenesulfonyl group, a trimethylsilyl group, a benzyloxycarbonyl group, a 3- or 4-chlorobenzyloxycarbonyl group, a benzylsulfonyl group, a benzyl group, a 4-nitrobenzyl group, a 4-methoxybenzyl group, a methyl group, an ethyl group, etc.).

[0156] The starting material, compound (1-1), may be a commercially available product or may be produced by a known method (e.g., WO2016 / 003929, WO2016 / 149393, etc.).

[0157] Compound (1-2) may be purchased commercially or prepared by a method described in known literature (e.g., WO2016 / 149393, Journal of Heterocyclic Chemistry, 15(8), 1295, 1978, Journal of Heterocyclic Chemistry, 44(2), 279, 2007, Eur. J. Med. Chem., 64, 54, 2013, J. Med. Chem., 2012, 55, 2945, J. Med. Chem., 2005, 48, 1984, Tetrahedron Letters, 57, 2888, 2016, WO2012 / 018668, etc.), or by a method described in known literature (e.g., R.C. Larock, "Comprehensive Organic Transformations", 2 ndEd., John Wiley and Sons, Inc., New York (1999), or the like.

[0158] Compound (1-5) may be purchased commercially or prepared by a method described in known literature (e.g., WO2008 / 008895, WO2011 / 118818, J. Med. Chem., 28(11), 1721, 1985, Tetrahedron, 67(52), 10208, 2011, TetrahedronLetters, 26(39), 4739, 1985, J. Antibiot. 59(4), 241, 2006, etc.), or by a method described in known literature (e.g., R.C. Larock, "Comprehensive Organic Transformations", 2 nd Ed., John Wiley and Sons, Inc., New York (1999), or the like).

[0159] The compounds (1-2) and (1-5) may be used as salts thereof, or may be used in which functional groups are protected, as necessary, as long as the salts do not interfere with the reaction.

[0160] Step 1-1: Compound (1-3) can be produced by reacting compound (1-1) with compound (1-2) in an inert solvent in the presence of a base under normal or increased pressure. Specific examples of the inert solvent include ether solvents such as THF or DME, halogenated hydrocarbon solvents such as dichloromethane or dichloroethane, and aprotic solvents such as N,N-dimethylformamide (DMF), N-methylpyrrolidone (NMP), and dimethyl sulfoxide (DMSO). Examples of the base include potassium tert-butoxide, sodium hydride, triethylamine, diisopropylethylamine, potassium carbonate, and sodium carbonate. The equivalent of the base used can be 0.001 to 100 equivalents relative to compound (1-1), and preferably 0.5 to 10 equivalents. The amount of compound (1-2) used relative to compound (1-1) is 0.001 to 100 equivalents, preferably 1 to 10. The reaction temperature is selected from the range of about -10°C to about 100°C.

[0161] Step 1-2: Compound (1-4) is prepared by removing the protecting group PG of compound (1-3). １ This step is described, for example, in the literature (TW Greene and PGM Wuts, "Protective Groups in Organic Synthesis", 3 rd Ed., John Wiley and Sons, Inc., New York (1999)).

[0162] Step 1-3: Compound (1-6) can be produced using Production Method (1-3-1) or Production Method (1-3-2) shown below. Step 1-3-1: When Y is an oxygen atom and T is a hydroxyl group, compound (1-6) can be produced by reacting compound (1-4) with compound (1-5) in an inert solvent in the presence of an azo compound analog and an organic phosphorus compound / or a phosphorane compound under normal or elevated pressure, under the conditions of the so-called Mitsunobu reaction. Specific examples of inert solvents include ether solvents such as THF or DME, and hydrocarbon solvents such as toluene or benzene. Examples of azo compound analogs include diethyl azodicarboxylate and diisopropyl azodicarboxylate. The molar equivalent of the azo compound analog can be 0.001 to 100 molar equivalents relative to compound (1-4), but is preferably 1 to 10 molar equivalents. Examples of organic phosphorus compounds include triphenylphosphine and tributylphosphine. The molar equivalent of the organic phosphorus compound can be 0.001 to 100 molar equivalents relative to compound (1-4), preferably 1 to 10 molar equivalents. Examples of phosphorane compounds include (cyanomethylene)tributylphosphorane and (cyanomethylene)trimethylphosphorane. The molar equivalent of the phosphorane compound can be 0.001 to 100 molar equivalents relative to compound (1-4), preferably 1 to 10 molar equivalents. The reaction temperature is selected from the range of about -10°C to about 100°C. Step 1-3-2: When Y is an oxygen atom, a sulfur atom, or -NR ｊ- and T is a leaving group (for example, a halogen atom such as chlorine, bromine, or iodine, a lower alkylsulfonyloxy group such as methanesulfonyloxy, a trihalogenomethanesulfonyloxy group such as trifluoromethanesulfonyloxy, an arylsulfonyloxy group such as benzenesulfonyloxy, or p-toluenesulfonyloxy), compound (1-6) can be produced by reacting compound (1-4) with compound (1-5) in an inert solvent in the presence of a base under atmospheric or elevated pressure. Specific examples of the inert solvent include ether solvents such as THF or DME, halogenated hydrocarbon solvents such as dichloromethane or dichloroethane, and aprotic solvents such as N,N-dimethylformamide (DMF), N-methylpyrrolidone (NMP), and dimethyl sulfoxide (DMSO). Specific examples of the base include potassium tert-butoxide, sodium hydride, triethylamine, diisopropylethylamine, potassium carbonate, sodium carbonate, and cesium carbonate. The molar equivalent of the base can be 0.001 to 100 molar equivalents relative to compound (1-1), preferably 0.5 to 10 molar equivalents. The molar equivalent of compound (1-5) can be 0.001 to 100 molar equivalents relative to compound (1-4), preferably 1 to 10 molar equivalents. The reaction temperature is selected from the range of about -10°C to about 100°C.

[0163] Step 1-4: This reaction can be carried out in accordance with known methods (e.g., WO2014 / 151958, WO2015 / 191907, WO2016 / 003929, etc.) from the corresponding compound (1-6). Preferably, the compound can be produced using the following production method (1-4-1) or production method (1-4-2). Production method (1-4-1): Compound (1-7) can be produced by reacting compound (1-6) as a starting material with a boronic acid in an inert solvent under acidic conditions. Examples of boronic acids include phenylboronic acid and 2-methylpropylboronic acid. The equivalent of the boronic acid used can be in the range of 0.001 to 100 equivalents relative to compound (1-6), preferably 1 to 3 equivalents. Examples of acids include hydrochloric acid and trifluoroacetic acid. The acid equivalent can be used in the range of 0.001 to 100 equivalents relative to compound (1-6), preferably 1 to 10 equivalents. Specific examples of inert solvents include halogenated hydrocarbon solvents such as dichloromethane or dichloroethane, hydrocarbon solvents such as hexane or heptane, ether solvents such as THF or CPME, nitrile solvents such as acetonitrile or propionitrile, and water, which can be used alone or as a mixed solvent. The above-listed acids can also be used directly as the solvent. A mixed solvent of hexane / acetonitrile is preferably used as the solvent. The reaction temperature is selected from the range of about -10°C to about 100°C. Production Method (1-4-2): Compound (1-7) can be produced by reacting compound (1-6) as a starting material with triethylsilane in trifluoroacetic acid solvent. The amount of triethylsilane used relative to compound (1-6) is in the range of 0.001 to 100 equivalents, preferably 1 to 50 equivalents. The reaction temperature is selected from the range of about -10°C to about 70°C.

[0164] Production Method 1A The compound of formula (1a) can be produced from the corresponding raw material which can be purchased or prepared in the same manner as the production method of the compound (1-7). Depending on the properties of the compound (1a), for example, a nucleophilic X －(X anion) (e.g., hydroxide anion HO － alkali metal salts which give １－６ C which generates alkoxide anion １－６ Alkoxide alkali metal salt, amide anion R ａ２ R ｂ１ N － The compound of formula (1b) may be obtained by reacting the compound of formula (1b) with an alkali metal salt of the amide, which gives (In the formula, X, Z, L １ , L ２ , G.R. １ , R ２ , R ３ , R ４ is as defined in item 1.) For example, among the compounds of formula (1a), a compound of the following formula (1a') in which X is a hydroxyl group may be treated with aqueous sodium hydroxide to obtain a sodium salt compound of formula (1b') depending on the properties of the compound. (In the formula, Z, L １ , L ２ , G.R. １ , R ２ , R ３ , R ４ is as defined in item 1. For example, in the compound of formula (1a), X is a hydroxyl group and R ４ A compound of the following formula (1a″) in which is a carboxyl group may be treated with aqueous sodium hydroxide to obtain a disodium salt compound of formula (1b″), depending on the properties of the compound. (In the formula, Z, L １ , L ２ , G.R. １ , R ２ , R ３ is as defined in item 1.)

[0165] Among the compounds of formula (1a), the compound represented by the following formula (2-7) can be produced, for example, by the following production method. １ Ga-NR ｄ (C═O)— and R ｄ represents the case of a hydrogen atom. (In the formula, L ２ , Y, Z, Ring A, L ３ , L ４ , G.R. １ , R ２ , R ４ , R ５ is as defined in item 1, and X ａ is a hydroxyl group or C １－６ is an alkoxy group, H is a hydrogen atom, and T, LG, PG １ , P.G. ２ , P.G. ３ , P.G. ４ are the same as defined in Production Method 1, and TMS represents a trimethylsilyl group.

[0166] The starting materials, Compound (1-1) and Compound (1-5), can be purchased commercially or prepared by the method described in Production Method 1. Compound (2-2) and Compound (2-3) can be purchased commercially or prepared from known compounds by known methods (for example, RC Larock, "Comprehensive Organic Transformations", 2 nd Ed., John Wiley and Sons, Inc., New York (1999), etc.) Compounds (1-5), (2-2), and (2-3) can be used as salts thereof, or compounds with protected functional groups as needed, as long as they do not interfere with the reaction.

[0167] Step 2-1: Compound (2-1) can be produced by reacting compound (1-1) with lithium hexamethyldisilazide in an inert solvent under normal or increased pressure. Specific examples of the inert solvent include ether solvents such as THF and diethyl ether. The amount of lithium hexamethyldisilazide used relative to compound (1-1) can be 0.001 to 100 equivalents, preferably 1 to 10 equivalents. The reaction temperature is selected from the range of about -78°C to about 50°C.

[0168] Step 2-2: Compound (2-4) can be produced by reacting compound (2-1) with compound (2-2) or (2-3) in an inert solvent in the presence or absence of a condensing agent and / or a base under normal or increased pressure. Specific examples of the inert solvent include ether solvents such as THF or DME, halogenated hydrocarbon solvents such as dichloromethane or chloroform, and aprotic solvents such as DMF, NMP, and DMSO. The amount of (2-2) or (2-3) used relative to compound (2-1) can be 0.001 to 100 equivalents, preferably 1 to 10 equivalents. As the condensing agent, various condensing agents commonly used in conventional methods can be used, including, for example, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (including hydrochloride), O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate, N,N'-dicyclohexylcarbodiimide, 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride and its hydrate. The equivalent of the condensing agent can be 0.001 to 100 equivalents relative to compound (2-1), preferably 1 to 10 equivalents. Examples of the base include diisopropylethylamine and triethylamine. The equivalent of the base can be 0.001 to 100 equivalents relative to compound (2-1), preferably 1 to 10 equivalents. The reaction temperature is selected from the range of about -78°C to about 100°C.

[0169] Step 2-3: Compound (2-5) can be produced using compound (2-4) as a starting material under conditions similar to those in step 1-2 of the above-mentioned Production Method 1.

[0170] Step 2-4: Compound (2-6) can be produced by using compound (2-5) as a starting material and reacting it with compound (1-5) under conditions similar to those in step 1-3 of the above-mentioned Production Method 1.

[0171] Step 2-5: Compound (2-7) can be produced using compound (2-6) as a starting material under conditions similar to those in step 1-4 of the above-mentioned Production Method 1.

[0172] Production Method 3 Among the compounds of formula (1a), the compound represented by the following formula (3-7) can be produced, for example, by the following production method. (In the formula, L １ , L ２ , Z, L ３ , L ４ , G.R. １ , R ２ , R ４ , R ５ is as defined in item 1, m and n are as defined in item 28, and X ａ is a hydroxyl group or C １－６ is an alkoxy group, H is a hydrogen atom, and T, LG, PG ２ , P.G. ３ , P.G. ４ are the same as defined in Production Method 1, and PG ５ represents a protecting group for an amino group (for example, ethoxycarbonyl group, tert-butoxycarbonyl group, acetyl group, benzoyl group, trifluoroacetyl group, benzyloxycarbonyl group, 3- or 4-chlorobenzyloxycarbonyl group, triphenylmethyl group, methanesulfonyl group, p-toluenesulfonyl group, trimethylsilyl group, benzyloxycarbonyl group, 3- or 4-chlorobenzyloxycarbonyl group, benzylsulfonyl group, benzyl group, 4-nitrobenzyl group, 4-methoxybenzyl group, methyl group, ethyl group, etc.), and J represents a hydroxyl group or a leaving group (for example, a halogen atom such as chlorine, bromine, or iodine, a lower alkylsulfonyloxy group such as methanesulfonyloxy, a trihalogenomethanesulfonyloxy group such as trifluoromethanesulfonyloxy, an arylsulfonyloxy group such as benzenesulfonyloxy or p-toluenesulfonyloxy, etc.).

[0173] The starting materials, Compound (3-1) and Compound (3-2), can be purchased commercially or prepared by the methods described in Production Method 1 and Production Method 2. Compound (3-2) and Compound (3-5) can be purchased commercially or prepared from known compounds by known methods (for example, see RC Larock, "Comprehensive Organic Transformations", 2002). nd Ed., John Wiley and Sons, Inc., New York (1999), etc.) Compounds (3-2) and (3-5) can be used as salts thereof, or compounds with protected functional groups as needed, as long as they do not interfere with the reaction.

[0174] Step 3-1: Compound (3-3) can be produced by reacting compound (3-1) as a starting material with compound (3-2) under conditions similar to those in step 1-3 of Production Method 1.

[0175] Step 3-2: Compound (3-4) is prepared by removing the protecting group PG of compound (3-3). ５ This step is described, for example, in the literature (TW Greene and PGM Wuts, "Protective Groups in Organic Synthesis", 3 rd Ed., John Wiley and Sons, Inc., New York (1999)).

[0176] Step 3-3: Compound (3-6) can be produced using compound (3-4) as a starting material under conditions similar to those in step 2-2 of the above-mentioned Production Method 2.

[0177] Step 3-4: Compound (3-7) can be produced using compound (3-6) as a starting material under conditions similar to those in step 1-4 of the above-mentioned Production Method 1.

[0178] Production Method 4 Among the compounds of formula (1a), the compound represented by the following formula (4-4) can be produced, for example, by the following production method. (In the formula, Y, ring A, L ３ , L ４ , G.R. １ , R ２ , R ４ , R ５ is as defined in item 1, and X ａ is a hydroxyl group or C １－６ is an alkoxy group, H is a hydrogen atom, T, PG １ , P.G. ２ , P.G. ３ , P.G. ４ are the same as those defined in Production Method 1.)

[0179] The starting materials, Compound (4-1) and Compound (1-5), can be purchased commercially or prepared by the method described in Production Method 1. Compound (1-5) can be used as a salt thereof, or a compound with protected functional groups as needed, as long as it does not interfere with the reaction.

[0180] Step 4-1: Compound (4-2) can be produced using compound (4-1) as a starting material under conditions similar to those in step 1-2 of the above-mentioned Production Method 1.

[0181] Step 4-2: Compound (4-3) can be produced by reacting compound (4-2) as a starting material with compound (1-5) under conditions similar to those in step 1-3 of the above-mentioned Production Method 1.

[0182] Step 4-3: Compound (4-4) can be produced using compound (4-3) as a starting material under conditions similar to those in step 1-4 of the above-mentioned Production Method 1.

[0183] Production Method 5 Among the compounds of formula (1a), the compound represented by the following formula (5-4) can be produced, for example, by the following production method. (In the formula, L ３ , L ４ , G.R. １ , R ２ , R ４ , R ５is as defined in item 1, m and n are as defined in item 28, and X ａ is a hydroxyl group or C １－６ is an alkoxy group, H is a hydrogen atom, T, PG ２ , P.G. ３ , P.G. ４ are the same as defined in Production Method 1, and PG ５ , J has the same definition as described in Production Method 3.

[0184] The starting materials, Compound (4-1), Compound (3-2), and Compound (3-5), can be purchased commercially or produced by the methods described in Production Method 1 and Production Method 3. Compound (3-2) and Compound (3-5) can be used as salts thereof, or compounds with protected functional groups as needed, as long as they do not interfere with the reaction.

[0185] Step 5-1: Compound (5-1) can be produced by reacting compound (4-1) as a starting material with compound (3-2) under conditions similar to those in step 3-1 of the above-mentioned Production Method 3.

[0186] Step 5-2: Compound (5-2) can be produced using compound (5-1) as a starting material under conditions similar to those in step 3-2 of the above-mentioned Production Method 3.

[0187] Step 5-3: Compound (5-3) can be produced by reacting compound (5-2) as a starting material with compound (3-5) under conditions similar to those in step 3-3 of the above-mentioned Production Method 3.

[0188] Step 5-4: Compound (5-4) can be produced using compound (5-3) as a starting material under conditions similar to those in step 3-4 of the above-mentioned Production Method 3.

[0189] Production Method 6 Among the compounds of formula (1a), the compound represented by the following formula (6-5) can be produced, for example, by the following production method. (In the formula, L １ , L ２ , Y, Z, Ring A, L ３ , L ４ , G.R. ４ , R５ is as defined in item 1, except that one end of Y, R １ａ and R ２ａ are bonded to any of the three possible bonding positions on the benzene ring in the figure, which are unsubstituted, and R １ａ and R ２ａ is R as defined in paragraph 1 of this specification. １ , R ２ and R ３ represents the remaining two that do not have the structure of formula (2), and X ａ is a hydroxyl group or C １－６ is an alkoxy group, H is a hydrogen atom, and T, LG, PG １ , P.G. ２ , P.G. ３ , P.G. ４ are the same as those defined in Production Method 1.)

[0190] The starting materials, Compound (6-1), Compound (1-2), and Compound (1-5), can be purchased commercially or prepared by the method described in Production Method 1. Compound (3-2) and Compound (3-5) can be used as salts thereof, or compounds with protected functional groups as needed, as long as they do not interfere with the reaction.

[0191] Step (6-1): Compound (6-2) can be produced by reacting compound (6-1) as a starting material with compound (1-2) under conditions similar to those in step 1-1 of Production Method 1.

[0192] Step (6-2): Compound (6-3) can be produced using compound (6-2) as a starting material under conditions similar to those in step 1-2 of the above-mentioned Production Method 1.

[0193] Step (6-3): Compound (6-4) can be produced by reacting compound (6-3) as a starting material with compound (1-5) under conditions similar to those in step 1-3 of Production Method 1.

[0194] Step (6-4): Compound (6-5) can be produced using compound (6-4) as a starting material under conditions similar to those in step 1-4 of the above-mentioned Production Method 1.

[0195] Among the compounds of formula (1a), the compound represented by the following formula (7-5) can be produced, for example, by the following production method. １ Ga-NR ｄ (C═O)— and R ｄ represents the case of a hydrogen atom. (In the formula, L ２ , Y, Z, Ring A, L ３ , L ４ , G.R. ４ , R ５ is as defined in item 1, except that one end of Y, R １ａ and R ２ａ are bonded to any of the three possible bonding positions on the benzene ring in the figure, which are unsubstituted, and R １ａ and R ２ａ is R as defined in paragraph 1 of this specification. １ , R ２ and R ３ represents the remaining two that do not have the structure of formula (2), and X ａ is a hydroxyl group or C １－６ is an alkoxy group, H is a hydrogen atom, and T, LG, PG １ , P.G. ２ , P.G. ３ , P.G. ４ are the same as defined in Production Method 1, and TMS represents trimethylsilyl.

[0196] The starting materials, Compound (6-1), Compound (1-2), and Compound (1-5), can be purchased commercially or prepared by the method described in Production Method 1. Compound (2-2) and Compound (2-3) can be purchased commercially or prepared from known compounds by known methods (for example, see RC Larock, "Comprehensive Organic Transformations", 2002). ndEd., John Wiley and Sons, Inc., New York (1999), etc.) Compounds (2-2), (2-3), and (1-5) can be used as salts thereof, or compounds with protected functional groups as needed, as long as they do not interfere with the reaction.

[0197] Step 7-1: Compound (7-1) can be produced using compound (6-1) as a starting material under conditions similar to those in step 2-1 of the above-mentioned Production Method 2.

[0198] Step 7-2: Compound (7-2) can be produced by reacting compound (7-3) as a starting material with compound (2-2) or compound (2-3) under conditions similar to those in step 2-2 of Production Method 2.

[0199] Step 7-3: The compound (7-3) can be produced using the compound (7-2) as a starting material under conditions similar to those in Step 2-3 of the above Production Method 2.

[0200] Step 7-4: Compound (7-4) can be produced by reacting compound (7-3) as a starting material with compound (1-5) under conditions similar to those in step 2-4 of the above-mentioned Production Method 2.

[0201] Step 7-5: Compound (7-5) can be produced using compound (7-4) as a starting material under conditions similar to those in step 2-5 of the above-mentioned Production Method 2.

[0202] Production Method 8 Among the compounds of formula (1a), the compound represented by the following formula (8-4) can be produced, for example, by the following production method. (In the formula, L １ , L ２ , Z, L ３ , L ４ , G.R. ４ , R ５ is as defined in item 1, except that one end of the oxygen atom substituted on the benzene ring, R １ａ and R ２ａ are bonded to any of the three possible bonding positions on the benzene ring in the figure, which are unsubstituted, and R１ａ and R ２ａ is R as defined in paragraph 1 of this specification. １ , R ２ and R ３ The remaining two of these do not have the structure of formula (2), m and n are as defined in item 28, and X ａ is a hydroxyl group or C １－６ is an alkoxy group, H is a hydrogen atom, T, PG ２ , P.G. ３ , P.G. ４ are the same as defined in Production Method 1, and PG ５ and J are as defined in Production Method 3.

[0203] The starting material, compound (6-3), can be purchased commercially or produced by the methods described in Production Method 1 and Production Method 2. Compounds (3-2) and (3-5) can be purchased commercially or produced by the method described in Production Method 3. As for compound (3-2) and compound (3-5), their salts can be used as long as they do not interfere with the reaction, and compounds with protected functional groups, if necessary, can also be used.

[0204] Step 8-1: Compound (8-1) can be produced by reacting compound (6-3) as a starting material with compound (3-2) under conditions similar to those in step 1-3 of the above-mentioned Production Method 1.

[0205] Step 8-2: The compound (8-2) can be produced using the compound (8-1) as a starting material under conditions similar to those in Step 3-2 of the above Production Method 3.

[0206] Step 8-3: Compound (8-3) can be produced by reacting compound (8-3) as a starting material with compound (3-5) under conditions similar to those in step 3-3 of the above-mentioned Production Method 3.

[0207] Step 8-4: The compound (8-4) can be produced using the compound (8-3) as a starting material under conditions similar to those in Step 1-4 of the above Production Method 1.

[0208] Production Method 9 Among the compounds of formula (1a), the compound represented by the following formula (9-4) can be produced, for example, by the following production method. (In the formula, Y, ring A, L ３ , L ４ , G.R. ４ , R ５ is as defined in item 1, except that one end of Y, R １ａ and R ２ａ are bonded to any of the three possible bonding positions on the benzene ring in the figure, which are unsubstituted, and R １ａ and R ２ａ is R as defined in paragraph 1 of this specification. １ , R ２ and R ３ represents the remaining two that do not have the structure of formula (2), and X ａ is a hydroxyl group or C １－６ is an alkoxy group, H is a hydrogen atom, and T, LG, PG １ , P.G. ２ , P.G. ３ , P.G. ４ are the same as those defined in Production Method 1.)

[0209] The starting materials, Compound (9-1) and Compound (1-5), can be purchased commercially or prepared by the method described in Production Method 1. Compound (1-5) can be used as a salt thereof, or a compound with protected functional groups as needed, as long as it does not interfere with the reaction.

[0210] Step 9-1: Compound (9-2) can be produced using compound (9-1) as a starting material under conditions similar to those in step 1-2 of the above-mentioned Production Method 1.

[0211] Step 9-2: Compound (9-3) can be produced by reacting compound (9-2) as a starting material with compound (1-5) under conditions similar to those in step 1-3 of the above-mentioned Production Method 1.

[0212] Step 9-3: Compound (9-4) can be produced using compound (9-3) as a starting material under conditions similar to those in step 1-4 of the above-mentioned Production Method 1.

[0213] Production Method 10 Among the compounds of formula (1a), the compound represented by the following formula (10-4) can be produced, for example, by the following production method. (In the formula, L ３ , L ４ , G.R. ４ , R ５ is as defined in item 1, and T, PG ２ , P.G. ３ , P.G. ４ are the same as defined in Production Method 1, except that one end of an oxygen atom substituted on a benzene ring, R １ａ and R ２ａ are bonded to any of the three possible bonding positions on the benzene ring in the figure, which are unsubstituted, and R １ａ and R ２ａ is R as defined in paragraph 1 of this specification. １ , R ２ and R ３ The remaining two of these do not have the structure of formula (2), m and n are as defined in item 28, and X ａ is a hydroxyl group or C １－６ is an alkoxy group, H is a hydrogen atom, and PG ５ , J has the same definition as described in Production Method 3.

[0214] The starting materials, Compound (9-2), Compound (3-2), and Compound (3-5), can be purchased commercially or produced by the methods described in Production Method 1 and Production Method 3. Compound (3-2) and Compound (3-5) can be used as salts thereof, or compounds with protected functional groups as needed, as long as they do not interfere with the reaction.

[0215] Step 10-1: Compound (10-1) can be produced by reacting compound (9-2) as a starting material with compound (3-2) under conditions similar to those in step 3-1 of the above-mentioned Production Method 3.

[0216] Step 10-2: The compound (10-2) can be produced using the compound (10-1) as a starting material under conditions similar to those in step 3-2 of the above-mentioned Production Method 3.

[0217] Step 10-3: Compound (10-3) can be produced by reacting compound (10-2) as a starting material with compound (3-5) under conditions similar to those in step 3-3 of Production Method 3.

[0218] Step 10-4: The compound (10-4) can be produced using the compound (10-3) as a starting material under conditions similar to those in Step 3-4 of the above Production Method 3.

[0219] Among the compounds of formula (1a), the compound represented by the following formula (11-3) can be produced, for example, by the following production method. ３ is -S (=O) ２ Represents the case of -. (In the formula, L １ , L ２ , Z, L ４ , G.R. １ , R ２ , R ４ , R ５ is as defined in item 1, m and n are as defined in item 28, and X ａ is a hydroxyl group or C １－６ is an alkoxy group, H is a hydrogen atom, and PG ２ , P.G. ３ , P.G. ４ are the same as those defined in Production Method 1.)

[0220] The starting material, compound (3-4), can be prepared by the method described in Production Method 3. Compound (11-1) can be purchased from a commercial product or prepared from a known compound by a known method (for example, see RC Larock, "Comprehensive Organic Transformations", 2002). nd Ed., John Wiley and Sons, Inc., New York (1999), etc. Compound (11-1) can be used as a salt thereof, or a salt in which functional groups are protected as needed, as long as it does not interfere with the reaction.

[0221] Step 11-1: Compound (11-2) can be produced by reacting compound (3-4) with compound (11-1) in an inert solvent, in the presence or absence of a base, under normal or increased pressure. Specific examples of the inert solvent include ether solvents such as THF or DME, halogenated hydrocarbon solvents such as dichloromethane or chloroform, and aprotic solvents such as DMF, NMP, and DMSO. The amount of compound (11-1) used relative to compound (3-4) can be 0.001 to 100 equivalents, preferably 1 to 10 equivalents. Examples of bases include diisopropylethylamine and triethylamine. The amount of base used relative to compound (3-4) can be 0.001 to 100 equivalents, preferably 1 to 10 equivalents. The reaction temperature is selected from the range of about −78° C. to about 100° C.

[0222] Step 11-2: The compound (11-3) can be produced using the compound (11-2) as a starting material under conditions similar to those in Step 1-4 of the above Production Method 1.

[0223] Among the compounds of formula (1a), the compound represented by the following formula (12-2) can be produced, for example, by the following production method. ３ is -S (=O) ２ Represents the case of -. (In the formula, L ４ , G.R. １ , R ２ , R ４ , R ５ is as defined in item 1, m and n are as defined in item 28, and X ａ is a hydroxyl group or C １－６ is an alkoxy group, H is a hydrogen atom, and PG ２ , P.G. ３ , P.G. ４ are the same as those defined in Production Method 1.)

[0224] The starting material, compound (5-2), can be prepared by the method described in Production Method 5. Compound (11-1) can be purchased from a commercial product or prepared from a known compound by a known method (for example, see RC Larock, "Comprehensive Organic Transformations", 2002). nd Ed., John Wiley and Sons, Inc., New York (1999), etc. Compound (11-1) can be used as a salt thereof, or a salt in which functional groups are protected as needed, as long as it does not interfere with the reaction.

[0225] Step 12-1: The compound (12-1) can be produced using the compound (5-4) as a starting material under conditions similar to those in Step 11-1 of the above Production Method 11.

[0226] Step 12-2: The compound (12-2) can be produced using the compound (12-1) as a starting material under conditions similar to those in Step 1-4 of the above Production Method 1.

[0227] Among the compounds of formula (1a), the compound represented by the following formula (13-5) can be produced, for example, by the following production method. ５ represents the case of an optionally substituted 1H-1,2,3-triazole. (In the formula, L ３ , L ４ , G.R. １ , R ２ , R ４ is as defined in item 1, m and n are as defined in item 28, and X ａ is a hydroxyl group or C １－６is an alkoxy group, H is a hydrogen atom, U is an amino group, a nitro group, a carboxylic acid, an alcohol, or a leaving group (for example, a halogen atom such as chlorine, bromine, or iodine, a lower alkylsulfonyloxy group such as methanesulfonyloxy, a trihalogen methanesulfonyloxy group such as trifluoromethanesulfonyloxy, or an arylsulfonyloxy group such as benzenesulfonyloxy or p-toluenesulfonyloxy), and R ｐ is R as defined in item 36 a Among these, a group acceptable for the compound of formula (13-4) or the R a PG is a group that can be converted into ２ , P.G. ３ , P.G. ４ are the same as defined in Production Method 1, and J is the same as defined in Production Method 3.

[0228] The starting material, compound (5-2), can be prepared by the method described in Production Method 5. Compound (13-1) can be purchased from a commercial product or prepared from a known compound by a known method (for example, see RC Larock, "Comprehensive Organic Transformations", 2002). nd Ed., John Wiley and Sons, Inc., New York (1999), etc. Compound (13-1) can be used as a salt thereof, or a salt in which functional groups are protected as needed, as long as it does not interfere with the reaction.

[0229] Step 13-1: The compound (13-2) can be produced using the compound (5-4) as a starting material under conditions similar to those in step 5-3 of the above-mentioned Production Method 5.

[0230] Step 13-2: Compound (13-3) can be produced by reacting compound (13-2) with an azidation agent in an inert solvent in the presence or absence of a base at normal pressure. Specific examples of the inert solvent include halogenated hydrocarbon solvents such as dichloromethane or chloroform, and aprotic solvents such as DMF, NMP, and DMSO. Specific examples of the azidation agent include sodium azide, trimethylsilyl azide, and diphenylphosphoryl azide. The amount of the azidation agent used relative to compound (13-2) can be 0.001 to 100 equivalents, preferably 1 to 10 equivalents. Examples of the base include diisopropylethylamine, triethylamine, and 4-dimethylaminopyridine. The amount of the base used relative to compound (13-2) can be 0.001 to 100 equivalents, preferably 1 to 10 equivalents. The reaction temperature is selected from the range of about -78°C to about 100°C.

[0231] Step 13-3: Compound (13-5) can be produced by reacting compound (13-3) with compound (13-4) in an inert solvent, in the presence or absence of a base, in the presence or absence of a catalyst, under normal or increased pressure. Specific examples of the inert solvent include ether solvents such as THF or DME, halogenated hydrocarbon solvents such as dichloromethane or chloroform, and aprotic solvents such as acetonitrile, DMF, NMP, and DMSO. The amount of compound (13-4) used relative to compound (13-3) can be 0.001 to 100 equivalents, preferably 1 to 10 equivalents. Examples of bases include diisopropylethylamine and triethylamine. The amount of base used relative to compound (13-3) can be 0.001 to 100 equivalents, preferably 1 to 10 equivalents. Specific examples of the catalyst include copper sulfate, copper iodide, and (chloro-[(1,2,3,4,5-h)-1,2,3,4,5-pentamethyl-2,4-pentacyclodien-1-yl]bis(triphenylphosphine)ruthenium(II). The catalyst can be used in an amount of 0.001 to 100 equivalents relative to compound (13-3), preferably 0.01 to 10 equivalents. The reaction temperature is selected from the range of about −78° C. to about 100° C.

[0232] Step 13-4: The compound (12-6) can be produced using the compound (12-5) as a starting material under conditions similar to those in Step 1-4 of the above Production Method 1.

[0233] The intermediates and target compounds in the above production methods can be isolated and purified by purification methods commonly used in organic synthetic chemistry (e.g., neutralization, filtration, extraction, washing, drying, concentration, recrystallization, various types of chromatography, etc.). Alternatively, each intermediate can be used in the next reaction without further purification.

[0234] Optically active compounds of the compounds of the present invention can be produced by using optically active starting materials or intermediates, or by optically resolving racemic intermediates or final products. Optical resolution methods include, but are not limited to, separation methods using optically active columns and fractional crystallization. Diastereomers of the compounds of the present invention can be produced by, but are not limited to, separation methods such as column chromatography and fractional crystallization.

[0235] A pharmaceutically acceptable salt of the compound represented by formula (1a) or formula (1b) can be produced by mixing the compound represented by formula (1) with a pharmaceutically acceptable acid or base in a solvent such as, but not limited to, water, methanol, ethanol, 2-propanol, ethyl acetate, or acetone.

[0236] In this specification, "or" is used when "at least one or more" of the items listed in the sentence can be employed. The same applies to "alternative." In this specification, when it is stated that "within a range of two values," the range includes the two values ​​themselves.

[0237] All references cited herein, including scientific literature, patents, patent applications, and the like, are incorporated by reference in their entirety to the same extent as if each were specifically set forth.

[0238] The present invention has been described above by showing preferred embodiments for ease of understanding. The present invention will be described below based on examples. However, the above description and the following examples are provided for illustrative purposes only and are not intended to limit the present invention. Therefore, the scope of the present invention is not limited to the embodiments or examples specifically described herein, but is limited only by the claims.

[0239] The present invention will be explained in more detail below with reference to Reference Examples, Examples and Test Examples, but the present invention is not limited to these examples.

[0240] The compounds were identified by proton nuclear magnetic resonance spectroscopy ( １H-NMR), liquid chromatography mass spectrometry (LCMS), etc. Tetramethylsilane was used as an internal standard for nuclear magnetic resonance spectroscopy.

[0241] For column chromatography in the Reference Examples and Examples, a silica gel column manufactured by Yamazen Corporation, an ODS-A column manufactured by YMC, and a YMC-Actus Triart C18 manufactured by YMC were used. For purification using thin layer chromatography (TLC), Silica gel 60F254 (Merck) was used for TLC (silica gel plate), and TLC plate NH (Fuji Silysia) was used for TLC (NH silica gel plate).

[0242] The various data described in the Reference Examples and Examples were obtained using the following instruments: NMR spectrum: １ H-NMR] 400 MHz: JEOL JNM-AL series AL400, JEOL EX270, and 500 MHz: JEOL ECA-500. 600 Hz: Agilent DD2 600 MHz NMR Spectrometer. LC-MS spectrum: Waters ACQUITY ＴＭ UltraPerformance LC, Waters AQUITY UPLC H-Class System, Shimadzu LCMS-2020.

[0243] The names of compounds described in Reference Examples and Examples are given using ACD / Name (ACD / Labs 12.0, Advanced Chemistry Development Inc.) and do not necessarily conform to the IUPAC nomenclature.

[0244] The measurement conditions (hereinafter also referred to as the measurement method) of the high performance liquid chromatography mass spectrometer (LCMS) are as follows, and the observed mass spectrometry value [MS (m / z)] is [M+1] ＋ The retention time at which the mass spectrometry value was observed is indicated by Rt (minutes, min). For each measured value, the measurement conditions used for the measurement are indicated by A to C. For example, "LCMS: [M+H] ＋ / Rt=620 / 1.32 Ａ" indicates that the measurement was performed under measurement condition A.

[0245] Measurement condition A Measurement equipment: Waters ACQUITY ＴＭ UltraPerformance LC Column: ACQUITY UPLC BEH C18 1.7 μm 2.1 × 30 mm column Solvent: Solution A: 0.05% HCOOH / H ２ Solution O, Solution B: CH ３ CN Gradient conditions: 0.0-1.3 min; A / B = 90 / 10 to 5 / 95 (linear gradient) 1.3-1.5 min; A / B = 90 / 10 Flow rate: 0.80 mL / min UV: 220 nm, 254 nm Column temperature: 40°C

[0246] Measurement Condition B Measurement equipment: Waters AQUITY UPLC H-Class System Column: Waters AQUITY UPLC HSS T3 1.8 μm 2.1 × 50 mm column Solvent: Solution A: 0.1% HCO ２ H / H ２ O, B liquid: 0.1% HCO ２ H / MeCN Gradient conditions: 0.0-2.4 min; A / B = 90 / 10 to 0 / 100 (linear gradient) 2.4-3.2 min; A / B = 0 / 100 Flow rate: 0.70 mL / min UV: 190-800 nm Column temperature: 40°C

[0247] Measurement condition C Measurement equipment: Waters ACQUITY ＴＭ UltraPerformance LC Column: ACQUITY UPLC BEH C18 1.7 μm 2.1 × 30 mm column Solvent: Solution A: 0.05% HCOOH / H ２ Solution O, Solution B: CH ３ CN Gradient conditions: 0.0-1.3 min; A / B = 99 / 1 to 5 / 95 (linear gradient) 1.3-1.5 min; A / B = 99 / 1 Flow rate: 0.80 mL / min UV: 220 nm, 254 nm Column temperature: 40°C

[0248] Measurement conditions D Measuring equipment: Waters AQUITY UPLC H-Class System Column: ACQUITY UPLC BEH C18 1.7 μm 2.1 x 50 mm column Solvent: Liquid A: HCOOH / CH ３ CN / H ２ O (0.05 / 50 / 49.95), B liquid: 0.05% HCOOH / CH ３ CN Gradient conditions: 0.0-4.0 min; A / B = 100 / 0 to 0 / 100 (linear gradient) 4.0-5.0 min; A / B = 0 / 100 Flow rate: 0.50 mL / min UV: 220 nm, 254 nm Column temperature: 40°C

[0249] Measurement condition E Measurement equipment: Waters ACQUITY ＴＭ UltraPerformance LC Column: ACQUITY UPLC BEH C18 1.7 μm 2.1 × 30 mm column Solvent: Solution A: 0.05% HCOOH / H ２ Solution O, Solution B: CH ３ CN Gradient conditions: 0.0-1.3 min; A / B = 60 / 40 to 5 / 95 (linear gradient) 1.3-1.5 min; A / B = 60 / 40 Flow rate: 0.80 mL / min UV: 220 nm, 254 nm Column temperature: 40°C

[0250] Measurement condition F Measurement equipment: Waters ACQUITY ＴＭ UltraPerformance LC Column: ACQUITY UPLC BEH C18 1.7 μm 2.1 × 30 mm column Solvent: Solution A: 0.05% HCOOH / H ２ Solution O, Solution B: CH ３ CN Gradient conditions: 0.0-1.3 min; A / B = 98 / 2 to 4 / 96 (linear gradient) 1.3-1.5 min; A / B = 98 / 2 Flow rate: 0.80 mL / min UV: 220 nm, 254 nm Column temperature: 40°C

[0251] Measurement condition G Measurement equipment: Shimadzu LCMS-2020 Column: Phenomenex Kinetex 1.7 μm C18 (50 mm × 2.10 mm) Solvent: Solution A: 0.05% TFA / H ２ Solution O, Solution B: CH ３ CN Gradient conditions: 0.0-1.9 min; A / B = 99 / 1 to 1 / 99 (linear gradient) 1.91-3.00 min; A / B = 1 / 99 Flow rate: 0.50 mL / min UV: 220 nm, 254 nm Column temperature: 40°C

[0252] Measurement Condition H Measurement equipment: Shimadzu LCMS-2020 Column: Phenomenex Kinetex 1.7 μm C18 (50 mm × 2.10 mm) Solvent: Solution A: 0.05% TFA / H ２ Solution O, Solution B: CH ３ CN Gradient conditions: 0.0-1.9 min; A / B = 90 / 10 to 1 / 99 (linear gradient) 1.91-3.00 min; A / B = 1 / 99 Flow rate: 0.50 mL / min UV: 220 nm, 254 nm Column temperature: 40°C

[0253] Measurement Condition I Measurement equipment: Waters AQUITY ＴＭ UPLC H-Class System Column: Waters AQUITY UPLC BEH C18 1.7 μm 2.1 × 50 mm column Solvent: Solution A: 0.05% HCO ２ H / H ２ O, B liquid: 0.05% HCO ２ H / MeCN Gradient conditions: 0.0-4.0 min; A / B = 90 / 10 to 0 / 100 (linear gradient) 4.0-5.0 min; A / B = 0 / 100 Flow rate: 0.50 mL / min UV: 220, 254 nm Column temperature: 40°C

[0254] In the Reference Examples, Examples, and Test Examples, the abbreviations shown above and the following abbreviations may be used to simplify the description. s: singlet d: doublet t: triplet q: quartet m: multiplet br: broad dd: doublet of doublets J: coupling constant Hz: Hertz δ: chemical shift min: minute THF: tetrahydrofuran DMAP: N,N-dimethyl-4-aminopyridine TFA: trifluoroacetic acid DIPEA: N,N-diisopropylethylamine DMF: dimethylformamide DME: 1,2-dimethoxyethane NMP: N-methylpyrrolidone DMSO: dimethylsulfoxide Me: methyl Et: ethyl MeCN: acetonitrile CPME: cyclopentyl methyl ether Boc: tert-butoxycarbonyl tBu or ｔ Bu or t-Bu: tert-butyl t-: tert- Bn: benzyl Cbz: benzyloxycarbonyl Trt: trityl (triphenylmethyl) Ms: methanesulfonyl, mesyl HATU: 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate N: normal M: mol / L, molar concentration MEPM: meropenem MIC: minimum inhibitory concentration

[0255] Reference Example 1: tert-butyl [1-(3-hydroxyazetidin-1-yl)ethylidene]carbamate

[0256] Reference Example 1-1: 3-bromo-2,6-dihydroxybenzoic acid N-Bromosuccinimide (6.06 g, 34.1 mmol) was added portionwise to a dichloromethane solution (59 mL) of 2,6-dihydrobenzoic acid (5 g, 32.4 mmol) and N,N-diisopropylethylamine (2.27 mL, 16.2 mmol) at -78°C. The reaction mixture was warmed to room temperature and stirred at the same temperature for 20 hours. The reaction mixture was evaporated under reduced pressure, and 1 mol / L hydrochloric acid (40 mL) was added to the resulting residue, followed by stirring at room temperature for 30 minutes. The precipitated crystals were collected by filtration, washed with water, and dried to give the title compound (6.03 g).

[0257] 1 H-NMR(CDCl3) δ: 7.58 (1H, d,J = 9.2 Hz), 6.53 (1H, d, J =8.5 Hz).

[0258] LCMS: [M+H] ＋ / Rt=233 / 0.412 min Ａ

[0259] Reference Example 1-2: tert-Butyl 3-bromo-2,6-bis[(tert-butoxycarbonyl)oxy]benzoate Di-tert-butyl dicarbonate (65.2 g, 299 mmol) and DMAP (0.608 g, 4.98 mmol) were added to a solution of the compound of Reference Example 1-1 (11.6 g, 49.8 mmol) in THF (120 mL) / tert-butanol (60 mL), and the mixture was stirred for 18 hours at 60° C. The reaction solution was cooled to room temperature, and the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: hexane / ethyl acetate=99 / 1 to 95 / 5) to give the title compound (19.3 g).

[0260] 1 H-NMR (CDCl3) δ: 7.60 (1H, d,J= 8.5 Hz), 7.02 (1H, d, J = 8.5 Hz), 1.53 (9H, s), 1.51 (9H, s).

[0261] Reference Example 1-3: tert-Butyl 2,6-bis[(tert-butoxycarbonyl)oxy]-3-ethenylbenzoate To a solution of the compound of Reference Example 1-2 (1.7 g, 3.47 mmol) in 1,4-dioxane (7 mL), tri-n-butylvinyltin (2.04 mL, 6.95 mmol) and bis(triphenylphosphine)palladium(II) chloride (0.488 g, 0.695 mmol) were added under a nitrogen atmosphere, and the mixture was stirred for 10 hours at 110° C. After cooling to room temperature, the reaction solution was evaporated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (eluent: hexane / ethyl acetate) to give the title compound (1.26 g).

[0262] 1H-NMR (CDCl3) δ: 7.57 (1H, d,J= 9.2 Hz), 7.11 (1H, d, J = 8.5 Hz), 6.73 (1H, dd, J = 17.7, 11.3Hz), 5.74(1H, d, J = 17.7 Hz), 5.37 (1H, d, J = 10.4 Hz), 1.57(9H, s), 1.54 (9H, s),1.52 (9H, s).

[0263] Reference Example 1-4: tert-Butyl 2,6-bis[(tert-butoxycarbonyl)oxy]-3-[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethyl]benzoate To a solution of the compound of Reference Example 1-3 (2.8 g, 6.41 mmol) in dichloromethane (32 mL) were added 1,4-bis(diphenylphosphino)butane (0.547 g, 1.28 mmol), bis(1,5-cyclooctadiene)diiridium(I) dichloride (0.431 g, 0.641 mmol), and pinacolatodiborane (1.40 mL, 9.62 mmol) under a nitrogen atmosphere, and the mixture was stirred at room temperature for 17 hours. The reaction solution was evaporated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (eluent: hexane / ethyl acetate) to give the title compound (3.59 g).

[0264] 1 H-NMR (CDCl3) δ: 7.30 (1H, d,J = 8.5 Hz), 7.01 (1H, d, J = 8.5 Hz),2.66-2.58 (2H, m), 1.53 (9H, s), 1.51(9H, s), 1.51 (9H, s), 1.20 (12H, s),1.10-1.02 (2H, m).

[0265] Reference Example 1-5: tert-Butyl 2,6-bis[(tert-butoxycarbonyl)oxy]-3-{2-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}benzoate To a solution of the compound of Reference Example 1-4 (0.976 g, 1.73 mmol) in THF (5 mL) was added (1S,2S,3R,5S)-(+)-pinanediol (0.736 g, 4.32 mmol), and the mixture was stirred at room temperature for 62 hours. The reaction mixture was evaporated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (eluent: hexane / ethyl acetate = 99 / 1 to 85 / 15) to give the title compound (0.90 g).

[0266] 1 H-NMR (CDCl3)δ: 7.31 (1H, d,J = 8.5 Hz), 7.01 (1H, d, J = 7.9 Hz), 4.23 (1H,dd, J = 8.5, 1.8 Hz), 2.69-2.60(2H, m), 2.35-2.24 (1H, m), 2.20-2.11(1H, m), 2.04-1.97 (1H, m), 1.91-1.76 (2H,m), 1.54 (9H, s), 1.51 (18H, s),1.34 (3H, s), 1.26 (3H, s), 1.14-1.07 (2H, m),1.02 (1H, d, J = 11.0Hz), 0.81 (3H, s).

[0267] LCMS: [MH] ＋ / Rt=615 / 3.160 min Ｂ

[0268] Reference Example 1-6: tert-Butyl 2-[(tert-butoxycarbonyl)oxy]-6-hydroxy-3-{2-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}benzoate Pyrrolidine (0.121 mL, 1.46 mmol) was added to a solution of the compound of Reference Example 1-5 (0.899 g, 1.46 mmol) in THF (5 mL), and the mixture was stirred at room temperature for 3 hours. The reaction mixture was evaporated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (eluent: hexane / ethyl acetate = 90 / 10 to 70 / 30) to give the title compound (0.68 g).

[0269] 1H-NMR (CDCl3)δ: 11.26 (1H,s), 7.33 (1H, d, J = 8.5 Hz), 6.82 (1H, d, J = 8.5Hz), 4.24 (1H, dd, J = 8.8,2.1 Hz), 2.63-2.54 (2H, m), 2.37-2.25 (1H, m), 2.23-2.11 (1H, m), 2.04-2.00 (1H, m), 1.93-1.78 (2H, m), 1.61 (9H, s), 1.54(9H, s), 1.36 (3H, s), 1.28 (3H, s),1.13-1.01 (3H, m), 0.83 (3H, s).

[0270] LCMS: [MH] ＋ / Rt=515 / 3.175 min Ｂ

[0271] Reference Example 1-7: Benzyl 3-[2-(tert-butoxycarbonyl)-3-[(tert-butoxycarbonyl)oxy]-4-{2-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-2H-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}phenoxy]azetidine-1-carboxylate Under a nitrogen atmosphere, cesium carbonate (4.01 g) was added to a solution of the compound of Reference Example 1-6 (2.117 g) and benzyl 3-iodoazetidine-1-carboxylate (1.95 g) in DMF (20.5 mL), and the mixture was heated to 50° C. After 9 hours, the reaction mixture was cooled to room temperature and poured into water, extracted with a mixed solvent of ethyl acetate and hexane (1:1), and concentrated. The residue was purified using a silica gel column to obtain the title compound (2.46 g).

[0272] 1H-NMR (CDCl3)δ: 7.36-7.26(5H, m), 7.18 (1H, d, J = 8.5 Hz), 6.36 (1H, d, J = 8.5 Hz), 5.08(2H, s),4.91-4.84 (1H, m), 4.37-4.27 (2H, m), 4.24-4.18 (1H, m), 4.09-4.03(2H, m), 2.58(2H, t, J = 8.2 Hz), 2.32-2.25 (1H, m), 2.18-2.08 (1H, m),2.04-1.95 (1H, m),1.89-1.84 (1H, m), 1.82-1.74 (1H, m), 1.53 (9H, s), 1.51(9H, s), 1.34 (3H, s),1.26 (3H, s), 1.08 (2H, t, J = 8.2 Hz), 1.00 (1H, d, J =11.0 Hz), 0.81 (3H, s).

[0273] Reference Example 1-8: tert-Butyl 6-[(azetidin-3-yl)oxy]-2-[(tert-butoxycarbonyl)oxy]-3-{2-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-2H-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}benzoate monohydrochloride To a solution of the compound of Reference Example 1-7 (0.4 g) in methanol (16 mL), 1N hydrochloric acid (0.567 mL) and 50% aqueous 10% palladium carbon (0.149 g) were added, and the mixture was stirred under hydrogen for 1 hour. After filtration through Celite, the mixture was concentrated to obtain the title compound (0.357 g).

[0274] 1H-NMR (CD3OD) δ: 7.31 (1H, d,J = 8.5 Hz), 6.66 (1H, d,J = 8.5 Hz), 5.14 (1H, m), 4.55-4.42 (2H, m),4.29-4.22 (1H, m), 4.13-4.05 (2H,m), 2.55 (2H, t, J = 8.2Hz), 2.35-2.30 (1H,m), 2.17-2.13 (1H, m), 1.99-1.92(1H, m), 1.87-1.80 (1H, m),1.79-1.72 (1H, m),1.56 (9H, s), 1.50 (9H, s), 1.33(3H, s), 1.27 (3H, s), 1.04 (2H, t, J = 8.2Hz), 0.98-0.96 (1H, m), 0.83 (3H, s).

[0275] Reference Example 1: tert-Butyl 6-[(1-acetylazetidin-3-yl)oxy]-2-[(tert-butoxycarbonyl)oxy]-3-{2-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-2H-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}benzoate To a solution of the compound of Reference Example 1-8 (0.1 g) in THF (0.8 mL), acetic anhydride (0.023 mL) and triethylamine (0.057 mL) were added in an ice bath, and the mixture was stirred overnight at room temperature. After concentration, the mixture was purified by silica gel column chromatography (ethyl acetate) to obtain the title compound (0.105 g).

[0276] 1H-NMR (CDCl3) δ: 7.19 (1H, d,J = 8.5 Hz), 6.39 (1H, d, J = 8.5 Hz), 4.93-4.88 (1H, m), 4.46-4.30 (2H, m),4.24-4.18 (1H, m), 4.16-4.00 (2H, m), 2.59 (2H, t, J=8.7 Hz), 2.35-2.23 (1H,m), 2.20-2.09 (1H, m), 2.01-1.96 (1H, m), 1.91-1.82(4H, m), 1.82-1.73 (1H, m),1.54 (9H, s), 1.49 (9H, d, J = 15.8 Hz), 1.32 (3H, t, J = 7.0 Hz), 1.25 (3H,s), 1.10 (2H, t, J = 8.7 Hz), 1.03-0.97 (1H, m), 0.81(3H, s).

[0277] Reference Example 2: tert-Butyl 6-[(1-methylsulfonylazetidin-3-yl)oxy]-2-[(tert-butoxycarbonyl)oxy]-3-{2-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-2H-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}benzoate The compound of Reference Example 1-8 was used as a starting material, and reaction, work-up and purification were carried out in the same manner as described in Reference Example 1 to obtain the title compound.

[0278] 1H-NMR (CDCl3)δ: 7.20 (1H, d,J = 8.5 Hz), 6.41 (1H, d, J = 8.5 Hz), 4.93-4.87 (1H, m),4.29-4.20 (3H, m),4.00-3.97 (2H, m), 2.89 (3H, s), 2.61-2.57(2H, m), 2.33-2.26(1H, m), 2.15 (1H,ddd, J = 13.7, 6.1, 3.4 Hz), 2.00 (1H, t, J = 5.5 Hz),1.87(1H, td, J = 6.3, 3.9Hz), 1.78 (1H, dt, J = 14.6, 2.7 Hz), 1.55 (9H, s), 1.51(9H, s) 1.34 (3H, s),1.26 (3H, s), 1.11-1.06 (2H, m), 1.00 (2H, d, J = 11.0Hz), 0.81 (3H, s).

[0279] Reference Example 3: tert-Butyl 2-[(tert-butoxycarbonyl)oxy]-6-({1-[(1H-imidazol-5-yl)acetyl]azetidin-3-yl}oxy)-3-{2-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-2H-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}benzoate HATU was added to a solution of the compound of Reference Example 1-8 (0.11 g), 4-imidazoleacetic acid hydrochloride (0.059 g), and triethylamine (0.076 mL) in DMF (0.905 mL) in an ice bath, and the mixture was slowly warmed to room temperature and stirred for 18 hours. The reaction mixture was poured into water, extracted with a mixed solvent of ethyl acetate and hexane (2:1), and concentrated. The residue was purified using a silica gel column to obtain the title compound (0.096 g).

[0280] 1H-NMR (CDCl3)δ: 8.19 (1H, s),7.21 (1H, d, J = 8.5 Hz), 7.00 (1H, s), 6.39 (1H, d, J = 8.5Hz), 4.90 (1H, m),4.61-4.59 (1H, m), 4.31-4.27 (1H,m), 4.23-21 (1H,m),4.7-4.05 (1H, m), 3.81-78(1H, m), 3.54 (2H, s), 2.58 (2H, m), 2.30-2.26 (2H,m), 2.17-2.13 (1H, m),2.02-1.98 (1H, m), 1.88-1.87 (1H, m), 1.80-1.77 (1H, m), 1.54 (9H, s), 1.51(9H, s), 1.33 (3H, s), 1.25 (3H, s), 1.10-1.06 (2H, m),1.22-1.10 (1H, s), 0.81(3H, s).

[0281] Using the compounds of Reference Examples 1 to 8 as starting materials, reactions, work-up and purification were carried out in the same manner as in Reference Example 3 to obtain Reference Example Compounds 4 to 34 shown in Table 2.

[0282] Reference Example 35: tert-Butyl 2-[(tert-butoxycarbonyl)oxy]-6-{[1-(hydroxycarbamoyl)azetidin-3-yl]oxy}-3-{2-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-2H-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}benzoate To a toluene solution of the compound of Reference Example 1-8 (76.4 mg) and DIPEA (0.066 mL), triphosgene (14.92 mg) was added at 0°C, and the mixture was allowed to warm to room temperature and stirred for 1.5 hours. The reaction mixture was concentrated, and to the residue, DMF (2.5 mL), DIPEA (0.5 mL), and hydroxylamine hydrochloride (51 mg) were added and stirred at room temperature for 3 hours. A saturated aqueous solution of sodium bicarbonate was added, and the mixture was extracted with ethyl acetate. The organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was subjected to silica gel column chromatography to obtain the title compound (56.5 mg) as a colorless solid.

[0283] 1 H-NMR (CDCl3) δ: 7.12 (1H, d,J = 8.5 Hz), 7.04(1H, s), 7.00 (1H, br s), 6.33 (1H, d, J = 8.5 Hz), 4.87-4.83(1H, m),4.34 (2H, dd, J = 9.8, 6.7 Hz), 4.17 (1H,dd, J = 8.5, 1.8 Hz),4.06-4.01(2H, m), 2.53 (2H, t, J = 8.5 Hz), 2.28-2.21 (1H, m),2.13-2.07 (1H, m), 1.95(1H, t, J = 5.5 Hz), 1.83-1.81 (1H, m),1.75-1.72 (1H, m), 1.49 (9H, s), 1.46(9H, s), 1.29 (3H, s), 1.21 (3H, s), 1.03 (2H, t, J = 8.5 Hz), 0.96 (1H, d, J =10.4 Hz), 0.76 (3H, s).

[0284] Reference Example (R)-36: tert-butyl 6-({1-[(2R)-2-[(tert-butoxycarbonyl)amino]-2-(1H-imidazol-4-yl)acetyl]azetidin-3-yl}oxy)-2-[(tert-butoxycarbonyl)oxy]-3-{2-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-2H-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}benzoate

[0285] Reference Example (S)-36: tert-butyl 6-({1-[(2R)-2-[(tert-butoxycarbonyl)amino]-2-(1H-imidazol-4-yl)acetyl]azetidin-3-yl}oxy)-2-[(tert-butoxycarbonyl)oxy]-3-{2-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-2H-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}benzoate

[0286] Reference Example 36-1: 4-formyl-N,N-dimethyl-1H-imidazole-1-sulfonamide Dimethylsulfamoyl chloride (91 mL, 859 mmol) was added dropwise to a chloroform solution (750 mL) of 1H-imidazol...

Claims

1. Formula (1a) or (1b): [In formula (2), Y represents an oxygen atom, a sulfur atom, or —NR ｊ -, ring A is an optionally substituted 4- to 20-membered non-aryl heterocycle, L ３ is -C(=O)-, -S(=O)-, or -S(=O) ２ - and L ４ is 1) a single bond, 2) C １－６ an alkylene group; 3) C ３－１０ 4) a cycloalkylene group, ６－１０ arylene group 5) a 5- or 6-membered heteroarylene group, or 6) a 4- to 10-membered non-aryl heterocyclylene group, 7) —C(═N—OR ｈ１ )-(wherein each of the substituents 2) to 6) above may be substituted), R ５ is 1) a hydrogen atom, 2) C １－６ an alkyl group; 3) C ３－１０ alicyclic group, 4) 4- to 10-membered non-aryl heterocycle, 5) C ６－１０ aryl, 6) 5- or 6-membered heteroaryl, 7) C １－６ an alkylthio group, or (provided that each of the substituents in 2) to 7) above may be substituted); 8) —NR ｅ１ OH], and (R １ , R ２ and R ３ the remaining two are the same or different and independently represent a hydrogen atom, a halogen atom, an optionally substituted C １－６ alkyl group, optionally substituted C １－６ an alkoxy group, optionally substituted C １－６ an alkylthio group, an optionally substituted 5- or 6-membered heteroaryl, or —NR ａ３ R ｂ２ and R ｄ , R ｅ１ , R ｅ２ , R ｆ１ , R ｆ２ , R ｇ１ , R ｇ２ , R ｈ１ , R ｈ２ , R ｉ１ , R ｉ２ and R ｊ are each independently the same or different and represent a hydrogen atom, an optionally substituted C １－６ alkyl group, optionally substituted C ３－１０ Alicyclic group, optionally substituted C ６－１０ aryl, an optionally substituted 5- or 6-membered heteroaryl, or an optionally substituted 4- to 10-membered non-aryl heterocycle; R ｅ１ and R ｆ１ or R ｅ２ and R ｆ２ When the combination of R is bonded to the same nitrogen atom, they may be joined together to form an optionally substituted 4- to 10-membered nitrogen-containing non-aryl heterocycle, ４ 1) -C(=O)R ８ , 2) -SO ２ -L ６ -R ８ (above 1) and 2) in the formula, R ８ is -NR ａ５ R ｂ４ , -NR ａ５ -L ７ -B(OR ｍ１ ) ２ , -OR ｍ１ or optionally substituted C １－６ is an alkyl group, and L ６ represents a single bond or -NR ａ６ -), 3) -NR ａ４ R ｂ３ , 4)-B(OR ｍ１ ) ２ , 5)-PO(OR ｍ１ ) (OR ｍ２ 6) an optionally substituted 5-membered heteroaryl, 7) an optionally substituted 5-membered non-aryl heterocycle, or 8) a bioisostere of any of 1) to 7) (provided that the formulae 2), 4), 5) and 6) above include carboxylic acid equivalents, and 8) may include these in duplicate), R ａ３ , R ａ４ , R ａ５ , R ａ６ , R ｂ２ , R ｂ３ and R ｂ４ are each independently the same or different and represent the R ａ１ , R ａ２ and R ｂ１ where R ａ３ and R ｂ２ , R ａ４ and R ｂ３ or R ａ５ and R ｂ４ When a combination of R is bonded to the same nitrogen atom, they may be joined together to form an optionally substituted 4- to 10-membered nitrogen-containing non-aryl heterocycle, ｍ１ is 1) a hydrogen atom, 2) C １－６ an alkyl group; 3) C ３－１０ Alicyclic group, 4)C ６－１０ 5) aryl, 5) 5- or 6-membered heteroaryl, or 6) 4- to 10-membered non-aryl heterocycle (provided that each of the substituents in 2) to 6) above may be substituted), provided that R ｍ１ is bonded to the boron atom via an oxygen atom, two R ｍ１ is C ２－４ The alkylene may be taken together with the boron atom and two oxygen atoms to form a 5- to 7-membered non-aryl heterocycle (the alkylene portion of the non-aryl heterocycle may be substituted), and R ｍ２ represents a hydrogen atom, an optionally substituted C １－６ an alkyl group or an optionally substituted C ３－１０ is an alicyclic group, ７ is an optionally substituted C １－３ or a pharmaceutically acceptable salt thereof.

2. L １ represents a single bond, a sulfur atom, or -NR ｄ C(=O)- or -NR ｄ SO ２ - and L ２ represents a single bond or an optionally substituted C １－６ an alkylene group, Z being 1) a hydrogen atom, 2) a hydroxyl group, 3) C ３－１０ Alicyclic group, 4)C ６－１０ aryl, 5) 5- or 6-membered heteroaryl, 6) 4- to 10-membered non-aryl heterocycle, 7) —C(═N—OR ｅ１ ) R ｆ１ , or 8) -NR ｅ１ R ｆ１ 2. The compound of claim 1, wherein:

3. Z-L ２ -L １ is a hydrogen atom, optionally substituted C １－６ an alkyl group or an optionally substituted C １－６ 3. The compound according to claim 1 or 2, or a pharmaceutically acceptable salt thereof, which is an alkylthio group.

4. Z-L ２ -L １ The compound according to any one of claims 1 to 3, or a pharmaceutically acceptable salt thereof, wherein is a hydrogen atom.

5. The compound according to any one of claims 1 to 4, or a pharmaceutically acceptable salt thereof, wherein G is an oxygen atom.

6. X is a hydroxyl group or an optionally substituted C １－６ The compound according to any one of claims 1 to 5, or a pharmaceutically acceptable salt thereof, wherein R is an alkoxy group.

7. The compound according to any one of claims 1 to 6, or a pharmaceutically acceptable salt thereof, wherein X is a hydroxyl group.

8. The compounds of formula (1a) and (1b) are represented by the following formulas (3a) and (3b), respectively: [In formulas (3a) and (3b), X, R １ , R ２ and R ３ is as defined in any one of claims 1 to 7, and R ４ is 1)-COOR ｍ１ (where R ｍ１ is a hydrogen atom, C １－６ Alkyl group, C ３－１０ Alicyclic group, C ６－１０ aryl, 5- or 6-membered heteroaryl, or 4- to 10-membered non-aryl heterocycle, wherein said C １－６ Alkyl group, ３－１０ alicyclic group, said C ６－１０ 1) a compound according to any one of claims 1 to 7, or a pharmaceutically acceptable salt thereof, wherein the compound is selected from the group consisting of: 1) an alkyl group selected from the group consisting of: aryl, the 5- or 6-membered heteroaryl, and the 4- to 10-membered non-aryl heterocycle, each of which is optionally substituted; and 2) a biological equivalent of 1).

9. R ４ 9. The compound of claim 8, wherein: is 1) —COOH (i.e., a carboxyl group); or 2) a carboxylic acid equivalent; or a pharmaceutically acceptable salt thereof.

10. The compounds of formula (1a) and (1b) or the compounds of formula (3a) and (3b) are represented by the following formulas (4a) and (4b), respectively: [In formulas (4a) and (4b), X, R ４ , Y, Ring A, L ３ , L ４ , and R ５ is as defined in any one of claims 1 to 9, and R １ and R ２ are each independently the same or different and represent a hydrogen atom, a halogen atom, or C １－６ Alkyl group, C １－６ Alkoxy group (provided that the C １－６ The alkyl group and the C １－６ The alkoxy group is optionally substituted with 1 to 5 halogen atoms.] or a pharmaceutically acceptable salt thereof.

11. The compound according to any one of claims 1 to 10, or a pharmaceutically acceptable salt thereof, wherein ring A is an optionally substituted 4- to 10-membered non-aryl heterocycle.

12. The compound according to any one of claims 1 to 11, or a pharmaceutically acceptable salt thereof, wherein ring A is an optionally substituted 4- to 7-membered non-aryl heterocycle.

13. The compound according to any one of claims 1 to 12, or a pharmaceutically acceptable salt thereof, wherein Y is an oxygen atom or a sulfur atom.

14. The compound according to any one of claims 1 to 13, or a pharmaceutically acceptable salt thereof, wherein Y is an oxygen atom.

15. The compounds of formulae (1a) and (1b), or the compounds of formulae (3a) and (3b), or the compounds of formulae (4a) and (4b) are represented by the following formulae (5a) and (5b), respectively: [In formulas (5a) and (5b), ring A is an optionally substituted 4- to 6-membered nitrogen-containing non-aryl heterocycle] or a pharmaceutically acceptable salt thereof.

16. L ３ is -C(=O)- or -S(=O) ２ 16. The compound according to any one of claims 1 to 15, wherein R is - or a pharmaceutically acceptable salt thereof.

17. L ３ The compound according to any one of claims 1 to 16, or a pharmaceutically acceptable salt thereof, wherein: is -C(=O)-.

18. L ４ is a single bond, -C(=N-OR ｈ１ )- or optionally substituted C １－６ an alkylene group, where R ｈ１ is optionally substituted C １－６ The compound according to any one of claims 1 to 17, which is an alkyl group, or a pharmaceutically acceptable salt thereof.

19. R １ and R ２ are each independently the same or different and are each independently selected from the group consisting of: 1) a hydrogen atom, 2) a halogen atom, 3) C １－６ 4) an alkyl group; １－６ an alkoxy group, and 5) C １－６ The compound according to any one of claims 1 to 18, or a pharmaceutically acceptable salt thereof, wherein the compound is selected from the group consisting of alkylthio groups (wherein each of the substituents 3) to 5) above is optionally substituted).

20. R １ and R ２ are each independently the same or different and are each independently selected from the group consisting of: 1) a hydrogen atom, 2) a halogen atom, 3) an optionally substituted C １－６ 20. The compound according to any one of claims 1 to 19, wherein the compound is selected from the group consisting of an alkyl group, or a pharmaceutically acceptable salt thereof.

21. R １ and R ２ The compound according to any one of claims 1 to 20, or a pharmaceutically acceptable salt thereof, wherein both are hydrogen atoms.

22. The compounds of formula (1a) and (1b), or the compounds of formula (3a) and (3b), or the compounds of formula (4a) and (4b), or the compounds of formula (5a) and (5b) are represented by the following formulas (6a) and (6b), respectively: [In formulas (6a) and (6b), L ３ , L ４ , and R ５ is as defined in any one of claims 1 to 18, m is an integer of 1, 2, or 3, n is an integer of 1, 2, or 3, and m+n is 2, 3, or 4.] The compound according to any one of claims 1 to 21, or a pharmaceutically acceptable salt thereof.

23. The compound according to any one of claims 1 to 22, or a pharmaceutically acceptable salt thereof, wherein m is 1 or 2, n is 1 or 2, and m+n is 2 or 3.

24. The compound according to any one of claims 1 to 23, wherein m is 1 and n is 1, or a pharmaceutically acceptable salt thereof.

25. L ４ is a single bond or -NR ２１ R ２２ Or = NOR ２３ C optionally substituted with １－６ an alkylene group, where R ２１ , R ２２ and R ２３ are each independently a hydrogen atom, an optionally substituted C １－６ The compound according to any one of claims 1 to 24, wherein the aryl group is an alkyl group, or an optionally substituted 4- to 10-membered non-aryl heterocyclic carbonyl group, or a pharmaceutically acceptable salt thereof.

26. L ４ is a single bond, -CH ２ -, -CH(NH ２ ) -, or -CH(NH ２ )-CH ２ -, where L ４ When an amino group is present in the ３ 26. The compound according to any one of claims 1 to 25, or a pharmaceutically acceptable salt thereof, which binds to:

27. L ４ is a single bond, -CH ２ -, -CMe(NH ２ )-, -CH(NHMe)-, -CD(NH ２ )-(wherein D represents a deuterium atom), -CH(NH ２ ) - or -CH ２ CH ２ 26. The compound according to any one of claims 1 to 25, wherein R is - or a pharmaceutically acceptable salt thereof.

28. L ４ is a single bond, -CH ２ -, or -CH(NH ２ 28. The compound of claim 27, or a pharmaceutically acceptable salt thereof, wherein:

29. R ５ represents a hydrogen atom, an optionally substituted C １－６ an alkyl group, an optionally substituted 4- to 10-membered non-aryl heterocycle, an optionally substituted C ６－１０ Aryl, optionally substituted 5- or 6-membered heteroaryl, optionally substituted C １－６ an alkylthio group, or —NR ｅ１ OH, where R ｅ１ represents a hydrogen atom or an optionally substituted C １－６ The compound according to any one of claims 1 to 28, which is an alkyl group, or a pharmaceutically acceptable salt thereof.

30. R ５ is an optionally substituted 5- or 6-membered heteroaryl or an optionally substituted C ６－１０ 30. The compound according to any one of claims 1 to 29, or a pharmaceutically acceptable salt thereof, which is aryl.

31. R ５ The compound according to any one of claims 1 to 29, or a pharmaceutically acceptable salt thereof, wherein: is an optionally substituted 5- or 6-membered heteroaryl.

32. R ５ The compound according to any one of claims 1 to 28, or a pharmaceutically acceptable salt thereof, wherein: is an optionally substituted 4- to 10-membered non-aryl heterocycle.

33. L ４ is a single bond, and R ５ is -NR ｅ１ OH, where R ｅ１ represents a hydrogen atom or an optionally substituted C １－６ The compound according to any one of claims 1 to 28, which is an alkyl group, or a pharmaceutically acceptable salt thereof.

34. L ４ is 1)-(CH ２ ) ｐ -CR １０ (N.H.R. １１ ) -, 2) -(CH ２ ) ｑ -CR １２ R １３ -, or 3)-(CH ２ ) ｐ -CR １０ (N.H.R. １１ )-(CH ２ ) ｑ -CR １２ R １３ - (wherein p and q are independently 0 or 1); R １０ is 1) a hydrogen atom, 2) a carboxyl group, 3) -C(=O)NR １０ａ R １０ｂ and R １１ is 1) a hydrogen atom, 2) -C(=O)R １１ａ or 3) an optionally substituted 5- or 6-membered non-aryl heterocyclic carbonyl group, provided that R １０ -C(=O)NR １０ａ R １０ｂ When R １０ｂ and R １１ Let's get together -CH ２ CH ２ - may be formed, R １２ is 1) a hydrogen atom, or 2) an optionally substituted C １－４ is an alkyl group, R １３ is 1) a hydrogen atom, 2) a hydroxyl group, or 3) an optionally substituted C １－４ 4) an alkyl group, 5) a sulfanyl group, 6) an optionally substituted C １－４ an alkylthio group, 7) —NR １３ａ R １３ｂ , 8)-NR １３ａ -C(=O)R １３ｂ 9) an optionally substituted 5- or 6-membered non-aryl heterocyclic carbonylamino group; 10) —NR １３ａ -C(=O)NR １３ｂ R １３ｃ , 11)-C(=O)NR １３ａ R １３ｂ , 12)-C(=O)NR １３ａ OR １３ｂ , 13)-S(=O) ２ -R １３ａ , 14)-S(=O) ２ -NR １３ａ R １３ｂ , 15)-C(=O)NR １３ａ -S(=O) ２ -R １３ｂ or 16) -C(=O)NR １３ａ -S(=O) ２ -NR １３ｂ R １３ｃ and R １０ａ , R １０ｂ , R １１ａ , R １３ａ , R １３ｂ and R １３ｃ are each independently a hydrogen atom or an optionally substituted C １－４ The compound according to any one of claims 1 to 24, or a pharmaceutically acceptable salt thereof, which is an alkyl group.

35. R ５ represents a hydrogen atom or an optionally substituted C １－４ 35. The compound of claim 34, or a pharmaceutically acceptable salt thereof, which is an alkyl group.

36. R ５ is as follows: and the subscript d is selected from the group consisting of R ５ is the number of substitutable positions on the ring of each R ６ａ are independently: 1) a hydrogen atom, 2) a hydroxyl group, 3) a cyano group, 4) a nitro group, 5) a halogen, 6) C １－４ 7) an alkyl group, ３－１０ Alicyclic group, 8)C １－４ 9) an alkoxy group; ３－１０ 10) an alicyclic oxy group, ６－１０ 11) an aryloxy group, 12) a 4- to 10-membered non-aryl heterocyclic oxy group (provided that each of the substituents in 6) to 12) above may be substituted), 13) —SO ２ -NR ｅ２ R ｆ２ , 14)-NR ｇ２ -CR ｅ２ (=NR ｆ２ ), 15)-NR ｇ２ -CR ｅ２ (=N-OR ｆ２ ), 16)-NR ｈ２ -C(=NR ｇ２ ) NR ｅ２ R ｆ２ , 17)-NR ｈ２ -C(=N-OR ｇ２ ) NR ｅ２ R ｆ２ , 18)-NR ｉ２ -C(=NR ｈ２ ) NR ｇ２ -NR ｅ２ R ｆ２ , 19)-NR ｉ２ -C(=N-OR ｈ２ ) NR ｇ２ -NR ｅ２ R ｆ２ , 20)-C(=NR ｅ２ ) R ｆ２ , 21)-C(=N-OR ｅ２ ) R ｆ２ , 22)-C(=NR ｈ２ )-NR ｅ２ R ｆ２ , 23)-C(=NR ｈ２ ) NR ｇ２ -NR ｅ２ R ｆ２ , 24)-C(=N-OR ｈ２ ) NR ｇ２ -NR ｅ２ R ｆ２ , 25)-NR ｅ２ R ｆ２ , 26)-NR ｇ２ -NR ｅ２ R ｆ２ , 27)-NR ｅ２ OR ｆ２ , 28)-NR ｅ２ -C(=O)R ｆ２ , 29)-C(=O)NR ｅ２ R ｆ２ , 30)-C(=O)NR ｅ２ OR ｆ２ , 31)-C(=O)NR ｇ２ -NR ｅ２ R ｆ２ , 32)-C(=O)R ｅ２ , 33)-C(=O)OR ｅ２ , and 34)-C(=N-OR ｈ２ ) NR ｅ２ R ｆ２ and each R is selected from the group consisting of ６ｂ are independently: 1) a hydrogen atom; 2) a hydroxyl group; 3) C １－４ an alkyl group (wherein the alkyl group may be substituted); 4) C ３－１０ an alicyclic group, (however, the alicyclic group may be substituted); 5) —C(═NR ｅ２ ) R ｆ２ , 6)-C(=N-OR ｅ２ ) R ｆ２ , 7)-SO ２ -NR ｅ２ R ｆ２ , 8)-C(=NR ｈ２ )-NR ｅ２ R ｆ２ , 9)-C(=NR ｈ２ ) NR ｇ２ -NR ｅ２ R ｆ２ , 10)-C(=N-OR ｈ２ ) NR ｇ２ -NR ｅ２ R ｆ２ , 11)-C(=O)NR ｅ２ R ｆ２ , 12)-C(=O)NR ｅ２ OR ｆ２ , 13)-C(=O)NR ｇ２ -NR ｅ２ R ｆ２ , 14)-C(=O)R ｅ２ , and 15)-C(=N-OR ｈ２ ) NR ｅ２ R ｆ２ 32. The compound according to any one of claims 1 to 31, selected from the group consisting of: or a pharmaceutically acceptable salt thereof.

37. R ５ is as follows: and the subscript d is a 5- or 6-membered aryl or heteroaryl selected from the group consisting of R ５ is the number of substitutable positions on the ring of each R ６ａ are independently: 1) a hydrogen atom, 2) a hydroxyl group, 3) a halogen, 4) C １－４ an alkyl group, wherein the alkyl group is NR ｅ２ R ｆ２ , a 5- or 6-membered non-aryl heterocycle, —C(═O)OR ｆ２ or may be substituted with a hydroxyl group) 5) C １－４ Alkoxy group 6) -NR ｅ２ R ｆ２ , and 7) —C(═O)OR ｅ２ and each R is selected from the group consisting of ６ｂ are independently: 1) a hydrogen atom, 2) a hydroxyl group, and 3) C １－４ an alkyl group, wherein the alkyl group is NR ｅ２ R ｆ２ , —C(═O)NR ｅ２ R ｆ２ , -C(=O)OR ｆ２ or a hydroxyl group).

38. R ｅ２ and R ｆ２ are each independently the same or different and represent a hydrogen atom, an optionally substituted C １－６ an alkyl group or an optionally substituted C ３－１０ The compound according to any one of claims 1 to 31, 36 and 37, which is an alicyclic group, or a pharmaceutically acceptable salt thereof.

39. R ｅ２ and R ｆ２ are each independently the same or different and represent a hydrogen atom or an optionally substituted C １－６ The compound according to any one of claims 1 to 31 and 36 to 38, which is an alkyl group, or a pharmaceutically acceptable salt thereof.

40. R ｅ２ and R ｆ２ The compound according to any one of claims 1 to 31 and 36 to 39, or a pharmaceutically acceptable salt thereof, wherein is a hydrogen atom.

41. R ６ａ is -NR ｅ２ R ｆ２ and R ｅ２ and R ｆ２ is a hydrogen atom on one side and a C atom on the other side. １－４ The compound according to any one of claims 36 to 39, wherein the alkyl group is an alkyl group (provided that the alkyl group is optionally substituted with an amino group or a hydroxyl group), or a pharmaceutically acceptable salt thereof.

42. R ５ is as follows: and the subscript d is a 4-6 membered non-aryl heterocycle selected from the group consisting of R ５ is the number of substitutable positions on the ring of each R ７ａ are independently: 1) a hydrogen atom, 2) a hydroxyl group, 3) a cyano group, 4) a halogen, 5) C １－４ 6) an alkyl group, ３－１０ Alicyclic group, 7)C １－４ an alkoxy group, 8) C ３－１０ 9) an alicyclic oxy group, C ６－１０ 10) an aryloxy group, 11) a 4- to 10-membered non-aryl heterocyclic oxy group, (provided that each of the substituents in 5) to 11) above may be substituted). 12) —SO ２ -NR ｅ３ R ｆ３ , 13)-NR ｇ２ -CR ｅ３ (=NR ｆ３ ), 14)-NR ｇ２ -CR ｅ３ (=N-OR ｆ３ ), 15)-NR ｈ２ -C(=NR ｇ２ ) NR ｅ３ R ｆ３ , 16)-NR ｈ２ -C(=N-OR ｇ２ ) NR ｅ３ R ｆ３ , 17)-NR ｉ２ -C(=NR ｈ２ ) NR ｇ２ -NR ｅ３ R ｆ３ , 18)-NR ｉ２ -C(=N-OR ｈ２ ) NR ｇ２ -NR ｅ３ R ｆ３ , 19)-C(=NR ｅ３ ) R ｆ３ , 20)-C(=N-OR ｅ３ ) R ｆ３ , 21)-C(=NR ｈ２ )-NR ｅ３ R ｆ３ , 22)-C(=NR ｈ２ ) NR ｇ２ -NR ｅ３ R ｆ３ , 23)-C(=N-OR ｈ２ ) NR ｇ２ -NR ｅ３ R ｆ３ , 24)-NR ｅ３ R ｆ３ , 25)-NR ｇ２ -NR ｅ３ R ｆ３ , 26)-NR ｅ３ OR ｆ３ , 27)-NR ｅ３ -C(=O)R ｆ３ , 28)-C(=O)NR ｅ３ R ｆ３ , 29)-C(=O)NR ｅ３ OR ｆ３ , 30)-C(=O)NR ｇ２ -NR ｅ３ R ｆ３ , 31)-C(=O)R ｅ３ , 32)-C(=O)OR ｅ３ , and 33)-C(=N-OR ｈ２ ) NR ｅ３ R ｆ３ and each R is selected from the group consisting of ７ｂ are independently: 1) a hydrogen atom; 2) a hydroxyl group; 3) C １－４ an alkyl group (wherein the alkyl group may be substituted); 4) C ３－１０ an alicyclic group, (however, the alicyclic group may be substituted); 5) —C(═NR ｅ３ ) R ｆ３ , 6)-C(=N-OR ｅ３ ) R ｆ３ , 7)-SO ２ -NR ｅ３ R ｆ３ , 8)-C(=NR ｈ２ )-NR ｅ３ R ｆ３ , 9)-C(=NR ｈ２ ) NR ｇ２ -NR ｅ３ R ｆ３ , 10)-C(=N-OR ｈ２ ) NR ｇ２ -NR ｅ３ R ｆ３ , 11)-C(=O)NR ｅ３ R ｆ３ , 12)-C(=O)NR ｅ３ OR ｆ３ , 13)-C(=O)NR ｇ２ -NR ｅ３ R ｆ３ , 14)-C(=O)R ｅ３ , and 15)-C(=N-OR ｈ２ ) NR ｅ３ R ｆ３ R is selected from the group consisting of ｅ３ and R ｆ３ is R according to claim 1 ｅ２ and R ｆ２ 33. The compound according to any one of claims 1 to 29 and 32, wherein R is a methyl group or a pharmaceutically acceptable salt thereof.

43. R ５ is as follows: and the subscript d is a 4-6 membered non-aryl heterocycle selected from the group consisting of R ５ is the number of substitutable positions on the ring of each R ７ａ are independently: 1) a hydrogen atom, 2) a hydroxyl group, 3) a halogen, 4) C １－４ an alkyl group, wherein the alkyl group is NR ｅ３ R ｆ３ , a 5- or 6-membered non-aryl heterocycle, —C(═O)OR ｆ３ or may be substituted with a hydroxyl group) 5) C １－４ Alkoxy group 6) -NR ｅ３ R ｆ３ , 7)-C(=O)OR ｅ３ , and 8) C ６－１０ Aryl 9) —C(═O)NR ｅ３ R ｆ３ and each R is selected from the group consisting of ７ｂ are independently: 1) a hydrogen atom, 2) a hydroxyl group, and 3) C １－４ an alkyl group, wherein the alkyl group is NR ｅ３ R ｆ３ , -C(=O)OR ｆ３ or a hydroxyl group), and R ｅ３ and R ｆ３ is R according to any one of claims 38 to 40. ｅ２ and R ｆ２ 43. The compound according to any one of claims 1 to 29, 32, and 42, wherein:

44. L ４ -CH(NH ２ )-CHR １３ -, and the NH ２ The carbon bonded to L ３ and R ５ is a hydrogen atom, and R １３ 1) -NH-C(=O)CH ３ , 2)-NH-C(=O)NH ２ , 3)-NH-C(=O)CH(NH ２ )-CH ２ C(=O)NH ２ , 4)-NH-C(=O)CH ２ -NH ２ , 5)-NH-C(=O)CH(NH ２ )-CH ２ OH, or 6) a pyrrolidin-2-ylcarbonylamino group, or a pharmaceutically acceptable salt thereof.

45. L ４ -CH(NH ２ )-CR １２ R １３ -, and the NH ２ The carbon bonded to L ３ and R ５ is a hydrogen atom or methyl, R １２ is a hydrogen atom or methyl, R １３ is a benzylthio group or a sulfanyl group. The compound according to any one of claims 1 to 24, 34, and 35, or a pharmaceutically acceptable salt thereof.

46. ​​L ４ -CH(NH ２ )-(CH ２ ) ｑ -CHR １３ -, q is 0 or 1, and the NH ２ The carbon bonded to L ３ and R ５ is a hydrogen atom, and R １３ is: 1) a carboxyl group, 2) -C(=O)NH ２ , 3)-C(=O)NH(CH ３ ), 4)-C(=O)N(CH ３ ) ２ , 5)-C(=O)NH-(CH ２ ) ２ -OH, 6) -C(=O)NH-(CH ２ ) ２ -NH ２ , 7)-C(=O)NH-S(=O) ２ -CH ３ , 8)-C(=O)NHOH, 9)-S(=O) ２ -NH ２ , 10)-S(=O) ２ -CH ３ 11) a hydroxyl group; or 12) a hydroxyl group; or a pharmaceutically acceptable salt thereof.

47. L ４ -CH(NHR １１ )-CH ２ -, and the NHR １１ The carbon bonded to L ３ and R ５ is hydrogen, and R １１ 1) -C(=O)CH(NH ２ )-CH ２ C(=O)NH ２ , 2)-C(=O)CH ２ -NH ２ , 3)-C(=O)CH(CH ３ )-NH ２ , 4)-C(=O)CH(NH ２ )-CH ２ OH, or 5) pyrrolidin-2-ylcarbonyl. The compound according to any one of claims 1 to 24, 34, and 35, or a pharmaceutically acceptable salt thereof.

48. L ４ -CH(NHR １１ )-CH(COOH)-, and the NHR １１ The carbon bonded to L ３ and R ５ is hydrogen, and R １１ 1) -C(=O)CH(NH ２ )-CH ２ C(=O)NH ２ , 2)-C(=O)CH ２ -NH ２ , 3)-C(=O)CH(CH ３ )-NH ２ , 4)-C(=O)CH(NH ２ )-CH ２ OH, or 5) pyrrolidin-2-ylcarbonyl. The compound according to any one of claims 1 to 24, 34, and 35, or a pharmaceutically acceptable salt thereof.

49. L ４ Ha-CHR １３ - or -CH ２ -CHR １３ - and R ５ is hydrogen, and R １３ is -C(=O)NH ２ or —C(═O)NHOH.

36. The compound according to any one of claims 1 to 24, 34, and 35, or a pharmaceutically acceptable salt thereof.

50. L ４ Ha-CH ２ -CR １０ (NH ２ )-, and the CH ２ The group is L ３ and R ５ is hydrogen, R １０ is a carboxy group or —C(═O)NH ２ The compound according to any one of claims 1 to 24, 34, and 35, wherein:

51. L ４ Ha-(CH ２ ) ｐ -CR １０ (N.H.R. １１ )-(CH ２ ) ｑ -CHR １３ -or-CHR １３ - (CH ２ ) ｑ -CR １０ (N.H.R. １１ )-(CH ２ ) ｐ -, where q is 0 or 1, R ５ is hydrogen, (1) L ４ Ga-CHR １３ - (CH ２ ) ｑ -CR １０ (N.H.R. １１ )-(CH ２ ) ｐ When -, the -CHR １３ The carbon of the - group is L ３ p is 0, and R １０ represents a hydrogen atom, a carboxyl group, or —C(═O)NHR １０ｂ and R １１ is a hydrogen atom, and R １０ｂ is a hydrogen atom, provided that R １０ -C(=O)NHR １０ｂ When R １０ｂ and R １１ Let's get together -CH ２ CH ２ - may be formed, R １３ is a hydrogen atom; (2) L ４ Ga-(CH ２ ) ｐ -CR １０ (N.H.R. １１ )-(CH ２ ) ｑ -CHR １３ -, the -(CH ２ ) ｐ The carbon of the - group is L ３ p is 1; R １０ and R １１ are both hydrogen atoms, and R １３ represents a carboxyl group or —C(═O)NR １３ａ R １３ｂ and R １３ａ and R １３ｂ are each independently a hydrogen atom or an optionally substituted C １－４ The compound according to any one of claims 1 to 24, 34, and 35, which is an alkyl group, or a pharmaceutically acceptable salt thereof.

52. L ４ is -CR １２ (NH ２ )- and R １２ is a hydrogen atom or a methyl group, R ５ is a C optionally substituted with one hydroxyl group １－４ The compound according to any one of claims 1 to 24, 34, and 35, which is an alkyl group, or a pharmaceutically acceptable salt thereof.

53. The compound according to claim 1, which is represented by the following compound name or structural formula, or a pharmaceutically acceptable salt thereof: 7-[(1-acetylazetidin-3-yl)oxy]-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinin-8-carboxylic acid. .

54. The compound according to claim 1, represented by the following compound name or structural formula, or a pharmaceutically acceptable salt thereof: 7-({1-[(2R)-2-amino-2-(1H-imidazol-4-yl)acetyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborimine-8-carboxylic acid. .

55. The following equation (11): [In formula (11), R Ｇ is a hydroxyl group, a thiol group, or -NHR ａ１ and R ａ１ , Z, L １ , L ２ , X, R １ , R ２ , R ３ , and R ４ has the same meaning as defined in claim 1, and formula (1a) has the same meaning as defined in claim 1, or a pharmaceutically acceptable salt thereof.

56. The compound of formula (11) is a compound of the following formula (12): [In formula (12), X, R １ , R ２ , R ３ , and R ４ is as defined in claim 8 ] or a pharmaceutically acceptable salt thereof.

57. The compound of formula (12) is a compound of the following formula (13): [In formula (13), X, Y, ring A, L ３ , L ４ , R １ , R ２ , R ４ , and R ５ is as defined in any one of claims 10 to 14 or claims 16 to 21, or a pharmaceutically acceptable salt thereof.

58. X and R Ｇ is a hydroxyl group, and R ４ is a carboxyl group, and ring A is an optionally substituted 4- to 6-membered nitrogen-containing non-aryl heterocycle, or a pharmaceutically acceptable salt thereof.

59. The compound of formula (13) is a compound of the following formula (14): [In formula (14), X, L ３ , L ４ , m, n, and R ５ has the same meaning as defined in claim 22] or a pharmaceutically acceptable salt thereof.

60. R Ｇ is a hydroxyl group or a thiol group, or a pharmaceutically acceptable salt thereof.

61. R Ｇ The compound according to any one of claims 55 to 60, or a pharmaceutically acceptable salt thereof, wherein is a hydroxyl group.

62. X is a hydroxyl group or C １－６ The compound according to any one of claims 55 to 61, or a pharmaceutically acceptable salt thereof, which is an alkoxy group.

63. The compound according to any one of claims 55 to 62, or a pharmaceutically acceptable salt thereof, wherein X is a hydroxyl group.

64. A compound according to any one of claims 59 to 63, or a pharmaceutically acceptable salt thereof, wherein m is 1 or 2, n is 1 or 2, and m+n is 2 or 3.

65. A compound according to any one of claims 59 to 64, or a pharmaceutically acceptable salt thereof, wherein m is 1 and n is 1.

66. L ３ The compound according to any one of claims 55 to 65, wherein is as defined in claim 16 or claim 17, or a pharmaceutically acceptable salt thereof.

67. L ４ and R ５ The compound according to any one of claims 55 to 66, wherein the compound has the same meaning as defined in any one of claims 18, 25 to 37, and 42 to 52, or a pharmaceutically acceptable salt thereof.

68. The compound of claim 55, or a pharmaceutically acceptable salt thereof, selected from the group consisting of: 6-[(1-acetylazetidin-3-yl)oxy]-3-(2-boronoethyl)-2-hydroxybenzoic acid. .

69. The compound of claim 55, or a pharmaceutically acceptable salt thereof, selected from the group consisting of the following compounds: 6-({1-[(2R)-2-amino-2-(1H-imidazol-4-yl)acetyl]azetidin-3-yl}oxy)-3-(2-boronoethyl)-2-hydroxybenzoic acid .

70. A medicine comprising a compound according to any one of claims 1 to 69 or a pharmaceutically acceptable salt thereof.

71. The pharmaceutical agent according to claim 70, which is a therapeutic or preventive agent for bacterial infections.

72. A β-lactamase inhibitor comprising, as an active ingredient, the compound according to any one of claims 1 to 69 or a pharmaceutically acceptable salt thereof.

73. A pharmaceutical composition comprising a compound according to any one of claims 1 to 69 or a pharmaceutically acceptable salt thereof and a pharmaceutically acceptable carrier.

74. The pharmaceutical composition of claim 73, further comprising an additional agent.

75. The pharmaceutical composition of claim 74, wherein the additional agent is selected from the group consisting of antibacterial agents, antifungal agents, antiviral agents, anti-inflammatory agents, and antiallergic agents.

76. The pharmaceutical composition of claim 74 or 75, wherein the additional agent is a β-lactam agent.

77. Additional drugs that are beta-lactams include amoxicillin, ampicillin (pivampicillin, hetacillin, bacampicillin, metampicillin, talampicillin), epicillin, carbenicillin (carindacillin), ticarcillin, temocillin, azlocillin, piperacillin, mezlocillin, mecillinam (pivmecillinam), sulbenicillin, benzylpenicillin (G), clometocillin, benzathine benzylpenicillin, procaine benzylpenicillin, azidocillin, penamecillin, phenoxymethylpenicillin (V), propionibacterial steroids (PPS), and benzodiazepines (BPS). Cirrhosis, benzathine phenoxymethylpenicillin, phenethicillin, cloxacillin (dicloxacillin, flucloxacillin), oxacillin, methicillin, nafcillin, faropenem, biapenem, doripenem, ertapenem, imipenem, meropenem, panipenem, tomopenem, razupenem, cefazolin, cephacetrile, cefadroxil, cephalexin, cephaloglycin, cephalonium, cephaloridine, cephalothin, cephapirin, cefatrizine, cefazedone, cefazaflur, cephradine, cefroxacillin ceftezole, cefaclor, cefamandole, cefminox, cefonicid, ceforanide, cefotiam, cefprozil, cefbuperazone, cefuroxime, cefuzonam, cefoxitin, cefotetan, cefmetazole, loracarbef, cefixime, ceftazidime, ceftriaxone, cefcapene, cefdaloxime, cefdinir, cefditoren, cefetamet, cefmenoxime, cefodizime, cefoperazone, cefotaxime, cefpimizole, cefpiramide, cefpodoxime, cefsulodin, cefteram, cef The pharmaceutical composition of claim 75 or 76, wherein the compound is selected from the group consisting of thibutene, ceftiolene, ceftizoxime, flomoxef, latamoxef, cefepime, cefozopran, cefpirome, cefquinome, ceftobiprole, ceftaroline, CXA-101, RWJ-54428, MC-04546, ME1036, BAL30072, SYN2416, ceftiofur, cefquinome, cefovecin, aztreonam, tigenonam, carumonam, RWJ-442831, RWJ-333441, and RWJ-333442.

78. The pharmaceutical composition of claim 76 or 77, wherein the β-lactam agent is selected from ceftazidime, biapenem, doripenem, ertapenem, imipenem, meropenem, or panipenem.

79. The pharmaceutical composition of claim 76 or 77, wherein the β-lactam drug is selected from aztreonam, tigenonam, BAL30072, SYN2416, or carumonam.

80. The pharmaceutical composition of claim 73, characterized in that it is administered in conjunction with an additional drug.

81. The pharmaceutical composition of claim 80, wherein the additional agent is selected from an antibacterial agent, an antifungal agent, an antiviral agent, an anti-inflammatory agent, or an antiallergic agent.

82. The pharmaceutical composition of claim 80 or 81, wherein the additional agent is a β-lactam agent.

83. Additional drugs that are beta-lactams include amoxicillin, ampicillin (pivampicillin, hetacillin, bacampicillin, metampicillin, talampicillin), epicillin, carbenicillin (carindacillin), ticarcillin, temocillin, azlocillin, piperacillin, mezlocillin, mecillinam (pivmecillinam), sulbenicillin, benzylpenicillin (G), clometocillin, benzathine benzylpenicillin, procaine benzylpenicillin, azidocillin, penamecillin, phenoxymethylpenicillin (V), propionibacterial steroids (PPS), and benzodiazepines (BPS). Cirrhosis, benzathine phenoxymethylpenicillin, phenethicillin, cloxacillin (dicloxacillin, flucloxacillin), oxacillin, methicillin, nafcillin, faropenem, biapenem, doripenem, ertapenem, imipenem, meropenem, panipenem, tomopenem, razupenem, cefazolin, cephacetrile, cefadroxil, cephalexin, cephaloglycin, cephalonium, cephaloridine, cephalothin, cephapirin, cefatrizine, cefazedone, cefazaflur, cephradine, cefroxacillin ceftezole, cefaclor, cefamandole, cefminox, cefonicid, ceforanide, cefotiam, cefprozil, cefbuperazone, cefuroxime, cefuzonam, cefoxitin, cefotetan, cefmetazole, loracarbef, cefixime, ceftazidime, ceftriaxone, cefcapene, cefdaloxime, cefdinir, cefditoren, cefetamet, cefmenoxime, cefodizime, cefoperazone, cefotaxime, cefpimizole, cefpiramide, cefpodoxime, cefsulodin, cefteram, cef The pharmaceutical composition of claim 81 or 82, wherein the compound is selected from the group consisting of thibutene, ceftiolene, ceftizoxime, flomoxef, latamoxef, cefepime, cefozopran, cefpirome, cefquinome, ceftobiprole, ceftaroline, CXA-101, RWJ-54428, MC-04546, ME1036, BAL30072, SYN2416, ceftiofur, cefquinome, cefovecin, aztreonam, tigenonam, carumonam, RWJ-442831, RWJ-333441, and RWJ-333442.

84. The pharmaceutical composition of claim 82 or 83, wherein the β-lactam agent is selected from the group consisting of ceftazidime, biapenem, doripenem, ertapenem, imipenem, meropenem, and panipenem.

85. The pharmaceutical composition of claim 82 or 83, wherein the β-lactam agent is selected from the group consisting of aztreonam, tigenonam, BAL30072, SYN2416, and carumonam.

86. A compound according to any one of claims 1 to 69 or a pharmaceutically acceptable salt thereof for treating a bacterial infection.

87. The compound according to claim 86 or a pharmaceutically acceptable salt thereof, wherein the bacterial infection is a bacterial infection involving a bacterium capable of having β-lactamase.

88. The compound according to claim 86 or 87, or a pharmaceutically acceptable salt thereof, wherein the bacterial infection is sepsis, febrile neutropenia, bacterial meningitis, bacterial endocarditis, otitis media, sinusitis, pneumonia, lung abscess, empyema, secondary infection of chronic respiratory disease, pharyngitis / laryngitis, tonsillitis, osteomyelitis, arthritis, peritonitis, intraperitoneal abscess, cholecystitis, cholangitis, liver abscess, deep skin infection, lymphangitis / lymphadenitis, secondary infection of trauma / burn, surgical wound, etc., urinary tract infection, genital infection, eye infection, or dental infection.

89. A pharmaceutical comprising a compound according to any one of claims 1 to 69 or a pharmaceutically acceptable salt thereof in combination with at least one drug selected from the group consisting of therapeutic agents for sepsis, febrile neutropenia, bacterial meningitis, bacterial endocarditis, otitis media, sinusitis, pneumonia, lung abscess, empyema, secondary infections of chronic respiratory lesions, pharyngitis / laryngitis, tonsillitis, osteomyelitis, arthritis, peritonitis, intraperitoneal abscess, cholecystitis, cholangitis, liver abscess, deep skin infections, lymphangitis / lymphadenitis, secondary infections such as trauma / burn and surgical wound, urinary tract infections, genital infections, eye infections, and dental infections.

90. A pharmaceutical composition comprising a β-lactam drug, wherein the pharmaceutical composition is administered in combination with a compound according to any one of claims 1 to 69 or a pharmaceutically acceptable salt thereof.

91. A method for treating a bacterial infection, comprising administering to a patient in need thereof a therapeutically effective amount of a compound according to any one of claims 1 to 69, or a pharmaceutically acceptable salt thereof.

92. The method of claim 91, wherein the bacterial infection is a bacterial infection involving a bacterium that may possess β-lactamase.

93. The method according to claim 91 or 92, wherein the bacterial infection is sepsis, febrile neutropenia, bacterial meningitis, bacterial endocarditis, otitis media, sinusitis, pneumonia, lung abscess, empyema, secondary infection of chronic respiratory disease, pharyngitis / laryngitis, tonsillitis, osteomyelitis, arthritis, peritonitis, intraperitoneal abscess, cholecystitis, cholangitis, liver abscess, deep skin infection, lymphangitis / lymphadenitis, secondary infection of trauma / burn, surgical wound, etc., urinary tract infection, genital infection, eye infection or dental infection.

94. The method of any one of claims 91 to 93, characterized in that it is administered in conjunction with an additional drug.

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