JP2001172245A - Aminobutanoic acid derivative - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide an aminobutanoic acid derivative inhibiting matrix metalloproteinase and useful for the prevention and/or treatment of rheumatism, arthrosteitis, pathologic bone resorption, osteoporosis, periodontosis, interstitial nephritis, arteriosclerosis, alveolar ectasia, hepatocirrhosis, corneus damage, metastatic invasion and proliferation of cancer cell, autoimmune disease (Crohn's disease, Sjoegren's disease, etc.), disease caused by the transmigration or infiltration of leukocyte cell through the vessel, vascularization, multiple sclerosis, aneurysm of aorta, endometriosis, etc. SOLUTION: The objective aminobutanoic acid derivative and its salt are expressed by formula (I) (the definitions of the symbols in the formula are described in the specification).

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to an aminobutanoic acid derivative, a method for producing the same, and a drug containing the derivative as an active ingredient. More specifically, general formula (I)

Embedded image (Wherein all symbols have the same meanings as described below), a non-toxic salt thereof, a method for producing them, and a drug containing them.

[0002]

2. Description of the Related Art Matrix metalloproteinase (hereinafter abbreviated as MMP) has zinc (hereinafter referred to as Z) at its active center.
Abbreviated as n ²⁺ . ) Is a neutral metalloproteinase that has the effect of degrading collagen, laminin, proteoglycan, fibronectin, elastin, gelatin, etc. under physiological conditions, thereby affecting the growth and remodeling of joint tissues, bone tissues, connective tissues, etc. are doing. As of MMP, ten or more molecular species having different primary structures have been identified so far. Specifically, interstitial collagenase (MMP-1), leukocyte collagenase (MM
P-8), gelatinase A (MMP-2), gelatinase B (MMP-9), stromlysin 1 (MMP-
3), stromlysin 2 (MMP-10), matrilysin (MMP-7), metalloelastase (MMP-
12) and the like.

[0003] As a property common to each of these enzymes,
(1) having Zn ²⁺ in the active center and requiring calcium ion (Ca ²⁺ ) for enzymatic activity; (2) being secreted as a latent enzyme and being activated extracellularly; (3) )
High homology to amino acid sequences, (4) resolution of various extracellular matrix components existing in vivo, (5) activity is inhibited by a common inhibitor, tissue metalloproteinase inhibitor (TIMP) That is known.

[0004] MMP inhibitors prevent various diseases caused by abnormally enhanced secretion and activity of MMP and / or prevent MMP.
Or it is considered useful for treatment. For example, rheumatism,
Osteoarthritis, pathological bone resorption, osteoporosis, periodontal disease, interstitial nephritis, arteriosclerosis, emphysema, cirrhosis, corneal injury, metastatic infiltration and proliferation of cancer cells, autoimmune diseases (Crohn's disease, Shugren's disease, etc.) And diseases due to vascular migration or infiltration of leukocyte cells, angiogenesis, multiple sclerosis, aortic aneurysm, endometriosis and the like.

[0005] Several compounds having a matrix metalloproteinase inhibitory action are known. Above all,
Substrate (Gly-Ile-Al) near the breakpoint of collagen
a-Gly or Gly-Leu-Ala-Gly)
Is known to have high affinity for collagenase. A number of chemically modified substrate analog matrix metalloproteinase inhibitors with a zinc affinity group at the cleavage site of this substrate have been studied [Inhibitors
of matrix metalloproteinases (MMP's), NigelRA Bee
ley, Phillip RJ Ansell, Andrew JP Docherty et Cur
r. Opin. Ther. Patents., 4 , 7-16 (1994), Current Drug
s Ltd ISSN 0962-2594]. However, these substrate analog inhibitors are expected to have various problems because they are peptide analogs. For this reason, it is desired to convert these inhibitors into non-peptides, and some have been reported.

For example, in the embodiment of the specification of EP 757037, the formula (W)

Embedded image It is disclosed that the sulfonyl amino acid derivative represented by has a matrix metalloproteinase inhibitory action.

[0007] In the examples of the specification of EP757984, formula (X)

Embedded image It is disclosed that the hydroxamic acid derivative represented by has a matrix metalloproteinase inhibitory action.

Examples of the specification of WO 9723459 include a compound represented by the formula (Y)

Embedded image It has been disclosed that the aromatic keto-acid derivative represented by the formula (1) has a matrix metalloproteinase inhibitory action.

Examples of the specification of WO9718188 include formula (Z)

Embedded image It has been disclosed that the hydroxamic acid derivative represented by has an inhibitory effect on the secretion of matrix metalloproteinase and TNFα.

[0010]

DISCLOSURE OF THE INVENTION The present inventors have conducted intensive studies to find compounds having an inhibitory effect on matrix metalloproteinases, such as gelatinase, stromlysin or collagenase, and as a result, have found that carboxylic acid amino derivatives of ^γ -amino acids It has been found that a novel aminobutanoic acid derivative represented by a certain general formula (I) achieves the object.

The present invention provides: 1) a compound represented by the following general formula (I):

Embedded image [Wherein, R ¹ represents -COOR ¹⁰ , -CONHOR ¹⁰ , -C
_{^{ONHNHR 10, - (CH 2)}} n SR 50 or -Y-PO
(OR ⁵¹ ) ₂ , wherein R ¹⁰ is (i) a hydrogen atom, (ii) C
A C1-8 alkyl group substituted by a 1-8 alkyl group, (iii) phenyl group, (iv) phenyl group or C1-8 alkoxy group, or (v) a phenyl group, benzyl group or C1-8 alkyl group substituted represents an oxycarbonyl group, n is an integer of 0 to 3, R ⁵⁰ is (i) hydrogen atom, (ii) C1-8 alkyl group, (iii) -COR
⁵² (in the group, R ⁵² represents a C1-8 alkyl group or a phenyl group), (iv) -SR ⁵³ (in the group, R ⁵³ represents a hydrogen atom, a C1-8 alkyl group or a phenyl group.)
R ⁵¹ represents a hydrogen atom, a C1-8 alkyl group or a phenyl group, Y represents a single bond, —CH ₂ — or —.
O-

R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , and R ⁷ are each independently 1) a hydrogen atom, 2) a C1-8 alkyl group, 3) a C2-8 alkenyl group, 4) —OR ^{11, 5) -SR 11, 6} ) -NR 12 R 13, 7) -COR 14, 8) Cyc1, 9) -OR 11, -SR 11, -NR 12 R 13, -COR 14,
C1~8 alkyl group selected from guanidino group or Cyc1 is substituted or ^{10) -OR 11, -SR 11,} , -NR 12 R 13, -CO
R ¹⁴ represents a C2-8 alkenyl group substituted by a group selected from a guanidino group or Cyc1, or R ³
Group and R ⁴ group together, a C1-8 alkylene group, R ⁵ group and R ⁶ group together, a C1-8 alkylene group, R ³ and R ⁶ group together, a C1-8 alkylene group Group, R ² group and R
³ groups together C2~8 alkylene group, R ⁴ group and R ⁵
C2~8 alkylene group together, or R ⁶ groups and R ⁷ groups represents a C2~8 alkylene group together, or

R ² represents a 2-propynyl group, and R ³ and R
⁴ , R ⁵ , R ⁶ , and R ⁷ are each independently 1) a hydrogen atom, 2) a C1-8 alkyl group, 3) a C2-8 alkenyl group, 4) —OR ¹¹ , 5) —SR ¹¹ , 6) ^{-NR 12 R 13, 7) -COR} 14, 8) Cyc1, 9) -OR 11, -SR 11, -NR 12 R 13, -COR 14,
C1~8 alkyl group selected from guanidino group or Cyc1 is substituted or ^{10) -OR 11, -SR 11,} , -NR 12 R 13, -CO
R ¹⁴ represents a C2-8 alkenyl group substituted by a group selected from a guanidino group or Cyc1, or R ³
Group and R ⁴ group together, a C1-8 alkylene group, R ⁵ group and R ⁶ group together, a C1-8 alkylene group, R ³ and R ⁶ group together, a C1-8 alkylene group Group, R ⁴ group and R
C2~8 alkylene group ⁵ groups together form or R ⁶ groups and R ⁷ groups together represent a C2~8 alkylene group,

In the group, Cyc1 represents a carbocycle or a heterocycle, and these carbocycles or heterocycles contain one or more (i) C1-8 alkyl groups, (ii) C1-8
Alkoxy group, (iii) nitro group, (iv) guanidino group, (v) amidino group, (vi) halogen atom, (vii) nitrile group, (viii) hydroxyl group, (ix) benzyloxy group,
(X) -NR ¹⁰¹ R ¹⁰² (R ¹⁰¹ and R ¹⁰² each independently represent a hydrogen atom or a C1-8 alkyl group), (xi) -COOR ¹⁰³ (R ¹⁰³ is a hydrogen atom or C1-8 Represents an alkyl group), (xii) a trifluoromethyl group, (xiii) a trifluoromethyloxy group,
(Xiv) phenyl group, (xv) phenyl group substituted by C1-8 alkyl group or C1-8 alkoxy group, (xvi) phenyloxy group, (xvii) phenylsulfonyl group, (xviii) phenyl group or nitrile group C1~8 alkyl group substituted by, (xix) heterocyclic or (xx) keto group, (xxi) -CONR ¹⁰⁴ in C1~8 alkoxy group (group substituted with R ¹⁰⁵ groups, R ¹⁰⁴ and R ¹⁰⁵
Each independently represents a hydrogen atom, a C1-8 alkyl group or a phenyl group. ) May be substituted.

R¹¹Is (i) a hydrogen atom, (ii) C1-8
Alkyl group, (iii) Cyc1 group, (iv) -COR¹⁸Group,
(V) -OR^Fifteen, -SR^Fifteen, -NR¹⁶R¹⁷, -CO
R¹⁸A guanidino group or a group selected from Cyc1
Represents a substituted C1-8 alkyl group,^FifteenIs a hydrogen atom,
A C1-8 alkyl group, Cyc1, or Cyc1 or
Is a C1-8 alkyl group substituted by a C1-8 alkoxy group
And R¹⁶Represents a hydrogen atom or a C1-8 alkyl group
And R¹⁷Is a hydrogen atom, a C1-8 alkyl group or-
COR¹⁹(In the group, R¹⁹Is a C1-8 alkyl group, Cyc1
Or a C1-8 alkyl group substituted by Cyc1
You. ) And R¹⁸Is a hydroxyl group, a C1-8 alkyl group,
C1-8 alkoxy group or -NR²⁰R ^{twenty one}(In the group, R²⁰
And R^{twenty one}Are each independently a hydrogen atom, C1-8
Alkyl group, Cyc1 or C1-8 substituted by Cyc1
Represents an alkyl group. ) And R¹²Is a hydrogen atom, C
1 to 8 alkyl groups, Cyc1 or Cyc1 substituted
Represents a C1-8 alkyl group,¹³Is a hydrogen atom, C1
8 alkyl groups, Cyc1, C1-8 substituted with Cyc1
Alkyl group or -COR^{twenty two}(In the group, R^{twenty two}Is C1-8
Alkyl group, Cyc1 or C1-8 substituted by Cyc1
Represents an alkyl group. ) And R¹⁴Is a hydroxyl group, C1
-8 alkyl group, C1-8 alkoxy group, Cyc1, C
a C1-8 alkyl group substituted with yc1 or -NR^{twenty three}R
^{twenty four}(In the group, R^{twenty three}And R^{twenty four}Are independently (i)
Hydrogen atom, (ii) C1-8 alkyl group, (iii) Cyc
1 or (iv) Cy1 or C1 substituted by a hydroxyl group;
Represents an 8 alkyl group. )

(1) R ⁸ is 1) a hydrogen atom, 2) C1-8 alkyl group, 3) C1-8 alkoxycarbonyl group, 4) —OR ²⁶ , —SR ²⁶ , —NR ²⁷ R ²⁸ or —COR
C1~8 alkyl group selected is replaced from ²⁹ or 5) when the Cyc2 represents a C1~8 alkoxycarbonyl group substituted,, R ⁹ is

Embedded image Represents

(2) R ⁸ is

Embedded image In the formula, R ⁹ represents 1) a C1-8 alkyl group, 2) a C1-8 alkoxy group, 3) a C1-8 alkoxy group substituted with Cyc2, 4) —OR ²⁶ , —SR ²⁶ , and —NR ²⁷ R ²⁸ , a group selected from -COR ²⁹ or Cyc2 is substituted C1~8 alkyl group or,

Embedded image Represents

In the group, Cyc2 represents a carbocycle or a heterocycle, and these carbocycles or heterocycles contain one or more (i) C1-8 alkyl groups, (ii) C1-8
Alkoxy group, (iii) nitro group, (iv) guanidino group, (v) amidino group, (vi) halogen atom, (vii) nitrile group, (viii) hydroxyl group, (ix) benzyloxy group,
(X) -NR ²⁰¹ R ²⁰² (R ²⁰¹ and R ²⁰² each independently represent a hydrogen atom or a C1-8 alkyl group), (xi) -COOR ²⁰³ (R ²⁰³ is a hydrogen atom or C1-8 Represents an alkyl group), (xii) a trifluoromethyl group, (xiii) a trifluoromethyloxy group,
(Xiv) phenyl group, (xv) phenyl group substituted by C1-8 alkyl group or C1-8 alkoxy group, (xvi) phenyloxy group, (xvii) phenylsulfonyl group, (xviii) phenyl group or nitrile group C1~8 alkyl group substituted by, (xix) heterocyclic or (xx) keto group, (xxi) -CONR ²⁰⁴ in C1~8 alkoxy group (group substituted with R ²⁰⁵ groups, R ²⁰⁴ and R ²⁰⁵
Each independently represents a hydrogen atom, a C1-8 alkyl group or a phenyl group. ) May be substituted.

R ²⁶ represents a hydrogen atom, a C1-8 alkyl group,
yc2 or a C1-8 alkyl group substituted by Cyc2, and R ²⁷ is a hydrogen atom, a C1-8 alkyl group, Cyc
2 or Cyc2 represents a substituted C1-8 alkyl group, and R ²⁸ represents a hydrogen atom, a C1-8 alkyl group, Cyc2,
A C1-8 alkyl group substituted with Cyc2 or -COR
³⁰ (R ³⁰ is a C1-8 alkyl group, Cyc2 or Cyc
2 represents a substituted C1-8 alkyl group. R ²⁹ represents a hydroxyl group, a C1-8 alkyl group, Cyc2,
yc2 is substituted C1~8 alkyl group or -NR ³¹ R
³² (R ³¹ and R ³² are each independently a hydrogen atom, C1
-8 alkyl group, Cyc2 or C substituted by Cyc2
Represents a 1-8 alkyl group. )

[0020]

Embedded image Represents a carbocyclic or heterocyclic ring, R ²⁵ represents -EG,

[0021] E is 1) a single ^{bond, 2) -CONR 33 -, 3} ) -NR 33 CO-, 4) -CO-O-, 5) -O-CO-, 6) -NR 33 -CO-NR ^{34 -, 7) -CO-CH} 2 -, 8) -CO-, 9) -O-CO-NR 33 -, 10) -NR 33 -CO-O-, 11) -O-CO-O-, ^{12) -CS-NR 33 -,} 13) -NR 33 -CS-, 14) -CS-O-, 15) -O-CS-, 16) -NR 33 -CS-R 34 -, 17) -CS _{-CH 2 -, 18) -CS-,} 19) -O-CS-NR 33 -, 20) -NR 33 -CS-O-, 21) -O-CS-O-, 22) -CH 2 -CH _{2 -, 23) -HC = CH-} , 24) -C≡C-, 25) -SO 2 -NR 33 -, 26) -NR 33 -SO 2 -, 27) -SO 2 -CH 2 -, or 2 ) -CH ₂ -SO ₂ - represents,

In the group, R ³³ and R ³⁴ each independently represent a hydrogen atom, a C1-8 alkyl group, Cyc3 or Cyc
3 represents a substituted C1-8 alkyl group, Cyc3 represents a carbocycle or a heterocycle, and these carbocycles or heterocycles contain one or more (i) C1-8 alkyl groups, (ii) C1 -8 alkoxy group, (iii) nitro group, (iv) guanidino group, (v) amidino group, (vi) halogen atom, (vii) nitrile group, (viii) hydroxyl group, (i
x) benzyloxy group, (x) -NR ³⁰¹ R ³⁰² (R ³⁰¹ and R ³⁰² each independently represent a hydrogen atom or
Represents an 8 alkyl group. ), (Xi) -COOR ³⁰³ (R
³⁰³ represents a hydrogen atom or a C1-8 alkyl group. ), (Xii) trifluoromethyl group, (xiii) trifluoromethyloxy group, (xiv) phenyl group, (xv)
A phenyl group substituted by a C1-8 alkyl group or a C1-8 alkoxy group, a (xvi) phenyloxy group, a (xvii) phenylsulfonyl group, a (xviii) a C1-8 alkyl group substituted by a phenyl group or a nitrile group , (Xix) a heterocycle or (xx) a keto group, (xxi) -C
A C1-8 alkoxy group substituted with an ONR ³⁰⁴ R ³⁰⁵ group (in the groups, R ³⁰⁴ and R ³⁰⁵ each independently represent a hydrogen atom, a C 1-8 alkyl group or a phenyl group)
May be substituted.

[0023] G is 1) hydrogen atom, 2) C1-8 alkyl group, 3) Cyc4, 4) -OR 35, 5) -SR 35, 6) halogen atom, 7) nitro group, 8) a nitrile group, 9 ^{) -NR 36 R 37, 10)} -COR 38, 11) Cyc4, -OR 35, -SR 35, halogen atom,
Group selected from -NR ³⁶ R ³⁷ or -COR ³⁸ represents a C1~8 alkyl group substituted,

In the group, Cyc4 represents a carbocycle or a heterocycle, and these carbocycles or heterocycles contain one or more (i) C1-8 alkyl groups, (ii) C1-8
Alkoxy group, (iii) nitro group, (iv) guanidino group, (v) amidino group, (vi) halogen atom, (vii) nitrile group, (viii) hydroxyl group, (ix) benzyloxy group,
(X) -NR ⁴⁰¹ R ⁴⁰² (R ⁴⁰¹ and R ⁴⁰² each independently represent a hydrogen atom or a C1-8 alkyl group), (xi) -COOR ⁴⁰³ (R ⁴⁰³ is a hydrogen atom or C1-8 Represents an alkyl group), (xii) a trifluoromethyl group, (xiii) a trifluoromethyloxy group,
(Xiv) phenyl group, (xv) phenyl group substituted by C1-8 alkyl group or C1-8 alkoxy group, (xvi) phenyloxy group, (xvii) phenylsulfonyl group, (xviii) phenyl group or nitrile group A C1-8 alkyl group substituted by (xix) a heterocycle, (x
x) a keto group, or a C1-8 alkoxy group substituted with a (xxi) -CONR ⁴⁰⁴ R ⁴⁰⁵ group, wherein R ⁴⁰⁴ and R ⁴⁰⁵
Each independently represents a hydrogen atom, a C1-8 alkyl group or a phenyl group. ) May be substituted.

R ³⁵ is a hydrogen atom, a C1-8 alkyl group,
Represents a 1-8 alkoxy group, Cyc4 or a C1-8 alkyl group substituted by Cyc4, and R ³⁶ represents a hydrogen atom, C1
-8 alkyl group, Cyc4 or C substituted by Cyc4
R ³⁷ represents a hydrogen atom, C 1-8
Alkyl, Cyc4, Cyc4 or C1-8 alkyl group substituted with -COR ³⁹ (R ³⁹ is. Representing a C1-8 alkyl group, C1-8 alkyl group Cyc4 or Cyc4 is substituted) represents, R ³⁸ is a hydroxyl group , C1-8 alkyl, Cyc4, Cyc4 is C1-8 alkyl group substituted, -NR ⁴⁰ R ⁴¹ (R ⁴⁰ and R ⁴¹ are each independently a hydrogen atom, C1-8 alkyl group, Cyc4 or C
Yc4 represents a substituted C1-8 alkyl group. ) Or together with -EG represent a C1-4 alkylidene group,

P represents an integer of 1 to 5, and M represents C1 to C8.
Represents an alkylene group, J is a single bond, an oxygen atom, a sulfur atom or -NR ⁴² - (R ⁴² represents a hydrogen atom or a C1~8 alkyl group.) Represent,

Embedded imageIs a single bond or R^Two, R^Three, R^Four, R^Five, R⁶, R⁷Out of
Two adjacent groups that are not bonded to the same carbon are hydrogen
In the case where R is removed, it represents a double bond (provided that R ^ThreeGroup and
R^FourGroups together form a C1-8 alkylene group, R^FiveGroup and R
⁶Groups together form a C1-8 alkylene group, R^ThreeGroup and R⁶
When the groups together represent a C1-8 alkylene group,
Does not represent a double bond. ).

However, when R ¹ is -COOR ¹⁰ or -CO
It represents NHOR ^10, and R ¹⁰ is a hydrogen atom or C1~
8 represents an alkyl group, and R ⁴ , R ⁵ and R ⁸ each represent a hydrogen atom, and one of R ² and R ³
One represents a methyl group, the other one represents a hydrogen atom,
And represent either one of ethoxymethoxy methyl R ⁶ and R ^7, when it remaining one represents a hydrogen atom, R ⁹
Is

Embedded image (4-phenoxyphenyl group) is not represented. An aminobutanoic acid derivative or a non-toxic salt thereof,

2) a method for producing the aminobutanoic acid derivative represented by the general formula (I) and a nontoxic salt thereof, and 3) the aminobutanoic acid derivative represented by the general formula (I) and the nontoxic salt thereof as an active ingredient It relates to the contained drug.

[Detailed Description of the Invention] In the present invention, all isomers are included unless otherwise indicated. For example, the alkyl group, the alkoxy group and the alkylene group include straight-chain and branched ones. Double bonds in alkenylene groups include those that are E, Z and EZ mixtures.
It also includes isomers resulting from the presence of asymmetric carbon atoms, such as when branched alkyl, alkoxy, and alkylene groups are present.

In the present invention, the C1-8 alkyl group is
Methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl groups and isomers thereof. C1-8 alkoxy group means methoxy, ethoxy,
Propoxy, butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy groups and isomers thereof.

A C1-8 alkyl group substituted by a phenyl group means methyl substituted by one phenyl group,
Ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl groups and isomers thereof. C1
A C1-8 alkyl group substituted by an 8 alkoxy group refers to methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy group and methyl, ethyl, Propyl, butyl, pentyl, hexyl, heptyl, octyl groups and isomers thereof.

A C1-8 alkyl group substituted by a nitrile group is defined as methyl substituted with one nitrile group,
Ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl groups and isomers thereof. An oxycarbonyl group substituted by a phenyl group is a phenyloxycarbonyl group. An oxycarbonyl group substituted by a benzyl group is a benzyloxycarbonyl group.

The oxycarbonyl group substituted by a C1-8 alkyl group includes methyloxycarbonyl, ethyloxycarbonyl, propyloxycarbonyl, butyloxycarbonyl, pentyloxycarbonyl, hexyloxycarbonyl, heptyloxycarbonyl, octyloxycarbonyl and the like. Is an isomer of

The C2-8 alkenyl group includes vinyl, propenyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, butadienyl, pentadienyl, hexadienyl, heptadienyl, octadienyl, hexatrienyl, heptatrienyl, octatrienyl and isomers thereof. It is.

The C1-8 alkylene group includes methylene, ethylene, trimethylene, tetramethylene, pentamethylene, hexamethylene, heptamethylene, octamethylene, and isomers thereof. The C2-8 alkylene group includes ethylene, trimethylene, tetramethylene, pentamethylene, hexamethylene, heptamethylene, octamethylene, and isomers thereof.

The halogen atom means a chlorine, bromine, fluorine or iodine atom. The C1-8 alkoxycarbonyl group is a methyloxycarbonyl, ethyloxycarbonyl, propyloxycarbonyl, butyloxycarbonyl, pentyloxycarbonyl, hexyloxycarbonyl, heptyloxycarbonyl, octyloxycarbonyl group and isomers thereof. C1-4 alkylidene group means methylidene, ethylidene, propylidene,
Butylidene and isomers thereof.

The carbocycle means a C3-15 monocyclic, bicyclic or tricyclic carbocycle. As these rings, for example,
Cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentene, cyclohexene, cyclopentadiene, cyclohexadiene,
Benzene, pentalene, indene, naphthalene, azulene, fluorene, phenanthrene, anthracene, acenaphthylene, biphenylene, perhydropentalene, perhydroindene, perhydronaphthalene, perhydroazulene, perhydrofluorene, perhydrophenanthrene, perhydroanthracene , Perhydroacenaphthylene, perhydrobiphenylene, adamantyl ring and the like.

Heterocycle means 1 to 4 nitrogen atoms, 1 to 2
Represents a 5- to 18-membered monocyclic, bicyclic or tricyclic heterocyclic ring containing one oxygen atom and / or one or two sulfur atoms.
A 5- to 18-membered monocyclic, bicyclic or tricyclic heterocycle containing from 1 to 4 nitrogen atoms, from 1 to 2 oxygen atoms and / or from 1 to 2 sulfur atoms is from 1 to 4 5 containing a nitrogen atom, 1-2 oxygen atoms and / or 1-2 sulfur atoms
Includes monocyclic, bicyclic or tricyclic heterocyclic aryls of up to 18 members or partially or fully saturated ones.

The above-mentioned compounds containing 1 to 4 nitrogen atoms, 1 to 2 oxygen atoms and / or 1 to 2 sulfur atoms
18-membered monocyclic, bicyclic or tricyclic heterocyclic aryl includes pyrrole, imidazole, triazole, tetrazole, pyrazole, pyridine, pyrazine, pyrimidine,
Pyridazine, azepine, diazepine, furan, pyran,
Oxepin, oxazepine, thiophene, thiane (thiopyran), tiepin, oxazole, isoxazole, thiazole, isothiazole, oxadiazole,
Oxaazine, oxadiazine, oxaazepine, oxadiazepine, thiadiazole, thiaazine, thiadiazine, thiazepine, thiadiazepine, indole, isoindole, benzofuran, isobenzofuran, benzothiophene, isobenzothiophene, indazole,
Quinoline, isoquinoline, phthalazine, naphthyridine,
Examples include quinoxaline, quinazoline, cinnoline, benzoxazole, benzothiazole, benzimidazole, carbazole, and acridine ring.

The above 5 to 5 containing 1 to 4 nitrogen atoms, 1 to 2 oxygen atoms and / or 1 to 2 sulfur atoms
Those partially or wholly saturated with an 18-membered monocyclic or bicyclic heterocyclic ring include pyrroline, pyrrolidine, imidazoline, imidazolidin, triazoline, triazolidine,
Tetrazoline, tetrazolidine, pyrazoline, pyrazolidine, piperidine, piperazine, tetrahydropyridine, tetrahydropyrimidine, tetrahydropyridazine, dihydrofuran, tetrahydrofuran, dihydropyran, tetrahydropyran, dihydrothiophene, tetrahydrothiophene, dihydrothiaine (dihydrothiopyran), tetrahydrothiaine (Tetrahydrothiopyran), dihydrooxazole, tetrahydrooxazole, dihydroisoxazole, tetrahydroisoxazole, dihydrothiazole, tetrahydrothiazole, dihydroisothiazole, tetrahydroisothiazole, morpholine, thiomorpholine, indoline, isoindoline, dihydrobenzofuran, perhydrobenzofuran , Dihydroi Benzofuran, perhydroisobenzofuran, dihydrobenzothiophene, perhydrobenzothiophene, dihydroisobenzothiophene, perhydroisobenzothiophene, dihydroindazole, perhydroindazole, dihydroquinoline, tetrahydroquinoline, perhydroquinoline, dihydroisoquinoline, tetrahydroisoquinoline, Perhydroisoquinoline, dihydrophthalazine, tetrahydrophthalazine, perhydrophthalazine, dihydronaphthyridine, tetrahydronaphthyridine, perhydronaphthyridine, dihydroquinoxaline, tetrahydroquinoxaline, perhydroquinoxaline, dihydroquinazoline, tetrahydroquinazoline, perhydroquinazoline, dihydrocinnoline , Tetrahydrocinnoline, peroxide Cinnoline, dihydrobenzoxazole, perhydrobenzoxazole, dihydrobenzothiazole, perhydrobenzothiazole, dihydrobenzimidazole, perhydrobenzimidazole, benzoxazepine, benzoxadiazepine, benzothiazepine, benzothiadiazepine, benzazepine , Benzodiazepine, indolooxoazepine, indolotetrahydrooxazepine, indolooxadiazepine, indolotetrahydrooxadiazepine, indolothiaazepine, indolotetrahydrothiaazepine, indolothiadiazepine, indolotetrahydrothiadiazepine , Indoloazepine, indolotetrahydroazepine, indolozezepine, indolotetrahydrodiazepine, benzofurazan, benzothia Diazole, benzotriazole, camphor, imidazothiazole, dihydrocarbazole,
Tetrahydrocarbazole, perhydrocarbazole,
Examples include dihydroacridine, tetrahydroacridine, perhydroacridine, dioxolane, dioxane, dithiolane, dithian, dioxazine, dithiazine ring and the like.

[0041]

[Salts] The present invention includes all non-toxic salts.
For example, common salts, acid addition salts, hydrate salts and the like can be mentioned. The compound of the present invention represented by the general formula (I) is converted into a corresponding salt by a known method. The salt is preferably a non-toxic, water-soluble salt. Suitable salts include salts of alkali metals (potassium, sodium, etc.), salts of alkaline earth metals (calcium, magnesium, etc.), ammonium salts, and pharmaceutically acceptable organic amines (tetramethylammonium, triethylamine, methylamine) Dimethylamine, cyclopentylamine, benzylamine, phenethylamine, piperidine, monoethanolamine, diethanolamine, tris (hydroxymethyl) amine, lysine, arginine, N-methyl-D-glucamine and the like.

The compound of the present invention represented by the general formula (I)
It is converted to the corresponding acid addition salt by known methods. The acid addition salts are preferably non-toxic and water-soluble. Suitable acid addition salts include inorganic acid salts such as hydrochloride, hydrobromide, sulfate, phosphate, nitrate, or acetate, trifluoroacetate, lactate, tartrate, oxalate Like, fumarate, maleate, citrate, benzoate, methanesulfonate, ethanesulfonate, benzenesulfonate, toluenesulfonate, isethionate, glucuronate, gluconate Organic acid salts.
Further, the compound of the present invention represented by the general formula (I) or a salt thereof can be converted into a hydrate by a known method.

Among the compounds of the present invention represented by the general formula (I), preferred are the compounds represented by the general formula (IA)

Embedded image (In the formula, all symbols have the same meanings as described above.)

Formula (IB)

Embedded image (In the formula, all symbols have the same meanings as described above.)

Formula (IC)

Embedded image (In the formula, all symbols have the same meanings as described above.)

Formula (ID)

Embedded image (In the formula, all symbols have the same meanings as described above.)

Formula (IE)

Embedded image (In the formula, all symbols have the same meanings as described above.)

General formula (IF)

Embedded image (In the formula, all symbols have the same meanings as described above.)

Formula (IG)

Embedded image (In the formula, all symbols have the same meanings as described above.)

Formula (IH)

Embedded image (In the formula, all symbols have the same meanings as described above.)

Formula (IJ)

Embedded image (In the formula, all symbols have the same meanings as described above.)

Formula (I-K)

Embedded image (In the formula, all symbols have the same meanings as described above.)

General formula (IL)

Embedded image (In the formula, all symbols have the same meanings as described above.)

Formula (IM)

Embedded image (In the formula, all symbols have the same meanings as described above.)

General formula (IN)

Embedded image (In the formula, all symbols have the same meanings as described above.)

General formula (IO)

Embedded image (In the formula, all symbols have the same meanings as described above.)

Formula (IP)

Embedded image (In the formula, G ¹ represents a methyl group, a halogen atom, a nitro group, or a nitrile group, and the other symbols have the same meanings as described above.)

Formula (IQ)

Embedded image (Wherein all symbols have the same meanings as described above).

More preferably, the following Tables 1 to 105
And the non-toxic salts thereof and the compounds described in Examples. In the following tables, Phth represents a phthalimide group, Ph represents a phenyl group, MOM represents a methoxymethyl group, EOM represents an ethoxymethyl group, MEM represents a (2-methoxyethoxy) methyl group, and BOM represents a benzyloxymethyl group.

[0060]

[Table 1]

[0061]

[Table 2]

[0062]

[Table 3]

[0063]

[Table 4]

[0064]

[Table 5]

[0065]

[Table 6]

[0066]

[Table 7]

[0067]

[Table 8]

[0068]

[Table 9]

[0069]

[Table 10]

[0070]

[Table 11]

[0071]

[Table 12]

[0072]

[Table 13]

[0073]

[Table 14]

[0074]

[Table 15]

[0075]

[Table 16]

[0076]

[Table 17]

[0077]

[Table 18]

[0078]

[Table 19]

[0079]

[Table 20]

[0080]

[Table 21]

[0081]

[Table 22]

[0082]

[Table 23]

[0083]

[Table 24]

[0084]

[Table 25]

[0085]

[Table 26]

[0086]

[Table 27]

[0087]

[Table 28]

[0088]

[Table 29]

[0089]

[Table 30]

[0090]

[Table 31]

[0091]

[Table 32]

[0092]

[Table 33]

[0093]

[Table 34]

[0094]

[Table 35]

[0095]

[Table 36]

[0096]

[Table 37]

[0097]

[Table 38]

[0098]

[Table 39]

[0099]

[Table 40]

[0100]

[Table 41]

[0101]

[Table 42]

[0102]

[Table 43]

[0103]

[Table 44]

[0104]

[Table 45]

[0105]

[Table 46]

[0106]

[Table 47]

[0107]

[Table 48]

[0108]

[Table 49]

[0109]

[Table 50]

[0110]

[Table 51]

[0111]

[Table 52]

[0112]

[Table 53]

[0113]

[Table 54]

[0114]

[Table 55]

[0115]

[Table 56]

[0116]

[Table 57]

[0117]

[Table 58]

[0118]

[Table 59]

[0119]

[Table 60]

[0120]

[Table 61]

[0121]

[Table 62]

[0122]

[Table 63]

[0123]

[Table 64]

[0124]

[Table 65]

[0125]

[Table 66]

[0126]

[Table 67]

[0127]

[Table 68]

[0128]

[Table 69]

[0129]

[Table 70]

[0130]

[Table 71]

[0131]

[Table 72]

[0132]

[Table 73]

[0133]

[Table 74]

[0134]

[Table 75]

[0135]

[Table 76]

[0136]

[Table 77]

[0137]

[Table 78]

[0138]

[Table 79]

[0139]

[Table 80]

[0140]

[Table 81]

[0141]

[Table 82]

[0142]

[Table 83]

[0143]

[Table 84]

[0144]

[Table 85]

[0145]

[Table 86]

[0146]

[Table 87]

[0147]

[Table 88]

[0148]

[Table 89]

[0149]

[Table 90]

[0150]

[Table 91]

[0151]

[Table 92]

[0152]

[Table 93]

[0153]

[Table 94]

[0154]

[Table 95]

[0155]

[Table 96]

[0156]

[Table 97]

[0157]

[Table 98]

[0158]

[Table 99]

[0159]

[Table 100]

[0160]

[Table 101]

[0161]

[Table 102]

[0162]

[Table 103]

[0163]

[Table 104]

[0164]

[Table 105]

[0165]

[Production Method of the Compound of the Present Invention] The compound of the present invention represented by the general formula (I) can be produced by the following methods or the methods described in Examples. [1] Among the compounds of the present invention represented by the general formula (I), R
A compound in which ¹ is -COOR ^10, that is, a compound represented by the general formula (I-
1)

Embedded image (Wherein all symbols have the same meanings as described above) can be produced by the following methods (a) to (c).

[0166] (a) -COOR ¹⁰ groups in the R ¹ group is -CO
Does not represent an OH group, and R ² , R ³ , R ⁴ , R ⁵ , R ⁶ ,
Any of the R ⁷ , R ⁸ and R ⁹ groups does not represent a —COOH group or a group containing the same, a hydroxyl group or a group containing the same, or an amino group or a group containing the same, ie, a compound represented by the general formula (I- 1a)

Embedded image ( ^Wherein , R ^10-1a represents a C1-8 alkyl group, a phenyl group, a C1-8 alkyl group substituted with a phenyl group or a C1-8 alkoxy group, or an oxy group substituted with phenyl, benzyl or a C1-8 alkyl group. ^Represents a carbonyl group, and represents R ^2-1a , R ^3-1a , R ^4-1a , R ^5-1a , R ^6-1a , R
^7-1a , R ^8-1a and R ^9-1a are respectively R ² , R ³ , R ⁴ , R ⁵ ,
It has the same meaning as R ⁶ , R ⁷ , R ⁸ and R ⁹ . Where R
^{2-1a, R 3-1a, R 4-1a,} R 5-1a, R 6-1a, R 7-1a, R
^{None of} the groups ^8-1a and ^{R9-1a represent} a -COOH group, a hydroxyl group or an amino group or a group containing them, and the other symbols have the same meanings as described above. The compound represented by the general formula (II)

Embedded image (Wherein all symbols have the same meanings as described above) and a compound represented by the general formula (III):

Embedded image (Wherein all symbols have the same meanings as described above), and can be produced by subjecting the compound to an amidation reaction.

The amidation reaction between the compound represented by the general formula (II) and the compound represented by the general formula (III) is known. For example, (1) a method using an acid halide, and (2) a mixed acid anhydride. And (3) a method using a condensing agent.

These methods will be specifically described. (1) In the method using an acid halide, for example, a method in which a carboxylic acid is dissolved in an inert organic solvent (chloroform, methylene chloride, diethyl ether, tetrahydrofuran or the like) or without a solvent is used. An acid halide (oxalyl chloride, thionyl chloride, etc.) is reacted at −20 ° C. to reflux temperature, and the resulting acid halide is reacted with an amine in the presence of a tertiary amine (pyridine, triethylamine, dimethylaniline, dimethylaminopyridine, etc.). Inert organic solvent (chloroform, methylene chloride, diethyl ether, tetrahydrofuran, etc.)
The reaction is carried out at 0 to 40 ° C.

(2) In the method using a mixed acid anhydride, for example, a carboxylic acid is converted into an inert organic solvent (chloroform, methylene chloride, diethyl ether, tetrahydrofuran, etc.).
An acid halide (pivaloyl chloride, tosyl chloride, mesyl chloride, etc.) or an acid derivative (ethyl chloroformate, in the presence of a tertiary amine (pyridine, triethylamine, dimethylaniline, dimethylaminopyridine, etc.) in a medium or no solvent. Isobutyl chloroformate, etc.)
The mixture is reacted at 0 to 40 ° C., and the obtained mixed acid anhydride is reacted with the amine at 0 to 40 ° C. in an inert organic solvent (chloroform, methylene chloride, diethyl ether, tetrahydrofuran, etc.).
The reaction is performed by

(3) In the method using a condensing agent, for example, a carboxylic acid and an amine can be reacted with a tertiary amine (pyridine) in an organic solvent (chloroform, methylene chloride, dimethylformamide, diethyl ether, tetrahydrofuran or the like) or without a solvent. , Triethylamine, dimethylaniline, dimethylaminopyridine or the like) in the presence or absence of a condensing agent (1,3-dicyclohexylcarbodiimide (DC
C), 1-ethyl-3- [3- (dimethylamino) propyl] carbodiimide (EDC), 1,1′-carbonyldiimidazole (CDI), 2-chloro-1-methylpyridinium iodine, etc.) -With or without hydroxybenztriazole (HOBt);
The reaction is carried out at 40 ° C. These reactions (1), (2) and (3) are desirably performed under an inert gas (argon, nitrogen, etc.) atmosphere under anhydrous conditions.

[0171] (b) -COOR ¹⁰ groups in the R ¹ group is -CO
Does not represent an OH group, and R ² , R ³ , R ⁴ , R ⁵ , R ⁶ ,
R ^7, at least one group in R ⁸ and R ⁹ groups is -CO
A compound representing an OH group or a group containing the same, a hydroxyl group or a group containing the same, or an amino group or a group containing the same, that is, a compound represented by the general formula (I-1b):

Embedded image ^{(Wherein, R 2-1b, R 3-1b, R} 4-1b, R 5-1b, R 6-1b, R
^7-1b , R ^8-1b and R ^9-1b are respectively R ² , R ³ , R ⁴ , R ⁵ ,
It has the same meaning as R ⁶ , R ⁷ , R ⁸ and R ⁹ . Where R
^{2-1b, R 3-1b, R 4-1b,} R 5-1b, R 6-1b, R 7-1b, R
^8-1b , at least one of the R ^9-1b groups is -COO
Represents an H group, a hydroxyl group or an amino group or a group containing them, and other symbols have the same meanings as described above. ) Is a compound represented by the general formula (I-1a)
A compound in which an H group, a hydroxyl group, an amino group or a group containing them is protected, that is, a compound of the general formula (I-1a1)

Embedded image ( ^Where R ^2-1a1 , R ^3-1a1 , R ^4-1a1 , R ^5-1a1 , R
^6-1a1 , R ^7-1a1 , R ^8-1a1 , and R ^9-1a1 are each R ² ,
It has the same meaning as R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , and R ⁹ . However, R ^2-1a1 , R ^3-1a1 , R ^4-1a1 , R ^5-1a1 , R
^6-1a1, R ^7-1a1, at least one -COOH group group is protected out in ^{R 8-1a 1,} R 9-1a1 group (e.g., methyl group, ethyl group, t- butyl group and benzyl Group), protected hydroxyl group (for example, methoxymethyl group, tetrahydropyranyl group, t-butyldimethylsilyl group, acetyl group, benzyl group, etc.) or protected amino group (for example, benzyloxycarbonyl group, t- Butoxycarbonyl group, trifluoroacetyl group, etc.) or a group containing them, and other symbols have the same meanings as described above. ) Can be produced by subjecting the compound represented by the formula (1) to an alkali hydrolysis, a deprotection reaction under acidic conditions, a deprotection reaction of a silyl group, or a deprotection reaction by hydrogenolysis.

The deprotection reaction by alkali hydrolysis is known. For example, in an organic solvent (methanol, tetrahydrofuran, dioxane, etc.), an alkali metal hydroxide (sodium hydroxide, potassium hydroxide, lithium hydroxide, etc.), Alkaline earth metal hydroxides (barium hydroxide,
Calcium hydroxide, etc.) or carbonates (sodium carbonate,
The reaction is carried out at a temperature of 0 to 40 ° C. using potassium carbonate or the like or an aqueous solution thereof or a mixture thereof.

Deprotection reactions under acidic conditions are known,
For example, in an organic solvent (methylene chloride, chloroform, dioxane, ethyl acetate, anisole, etc.), an organic acid (acetic acid,
The reaction is performed at a temperature of 0 to 100 ° C. in trifluoroacetic acid, methanesulfonic acid, trimethylsilyl iodide or the like, or an inorganic acid (hydrochloric acid, sulfuric acid or the like) or a mixture thereof (hydrogen bromoacetic acid or the like). The deprotection reaction of the silyl group is known, and is carried out, for example, in a water-miscible organic solvent (tetrahydrofuran, acetonitrile, etc.) using tetrabutylammonium fluoride at a temperature of 0 to 40 ° C.

The deprotection reaction by hydrogenolysis is known, and examples thereof include an inert solvent [ether (eg, tetrahydrofuran, dioxane, diemethoxyethane, diethyl ether, etc.), alcohol (eg, methanol,
Ethanol, etc.), benzenes (eg, benzene, toluene, etc.), ketones (eg, acetone, methyl ethyl ketone, etc.), nitriles (eg, acetonitrile, etc.), amides (eg, dimethylformamide, etc.),
Water, ethyl acetate, acetic acid or a mixed solvent of two or more thereof] in the presence of a hydrogenation catalyst (eg, palladium-carbon, palladium black, palladium, palladium hydroxide, platinum dioxide, nickel, Raney nickel, etc.) In the presence of an acid (e.g., hydrochloric acid, sulfuric acid, hypochlorous acid, boric acid, tetrafluoroboric acid, etc.) or an organic acid (e.g., acetic acid, p-toluenesulfonic acid, oxalic acid, trifluoroacetic acid, formic acid, etc.) or 0 to 200 ° C. in the absence of hydrogen atmosphere at normal pressure or under pressure or in the presence of ammonium formate
At a temperature of When an acid is used, its salt may be used.

[0175] (c) -COOR ¹⁰ groups in the R ¹ group is -CO
A compound representing an OH group, that is, a compound of the general formula (I-1c)

Embedded image (Wherein all symbols have the same meanings as described above), are compounds represented by the aforementioned general formulas (I-1a) and (I-1b)
A compound of formula (I-1ab)

Embedded image (Wherein all symbols have the same meanings as described above). The compound can be produced by subjecting the compound to alkali hydrolysis, deprotection under acidic conditions or deprotection by hydrogenolysis. The hydrolysis under alkaline conditions, the deprotection reaction under acid conditions, and the deprotection reaction by hydrogenolysis are known and are carried out by the methods described above.

[2] Among the compounds of the present invention represented by the general formula (I), R ¹ is -CONHOR ¹⁰ or -CONNHN
Compounds which are HR ^10, i.e. formula (I-2)

Embedded image (Wherein R ^1-2 is -CONHOR ¹⁰ or -CONNHN
Represents HR ^10, the other symbols are the same meanings as described above. ) Can be produced by the following methods (a) and (b).

(A) R ¹ is -CONHOR ¹⁰ or -C
ONHNHR ¹⁰ and R ² , R ³ , R ⁴ , R ⁵ , R
⁶ , R ⁷ , R ⁸ and R ⁹ , all of which do not represent a —COOH group or a group containing the same, ie, a compound represented by the general formula (I-2a):

Embedded image ( ^Wherein R ^2-2a , R ^3-2a , R ^4-2a , R ^5-2a , R ^6-2a , R
^7-2a , R ^8-2a and R ^9-2a represent R ² , R ³ , R ⁴ , R ⁵ ,
It has the same meaning as R ⁶ , R ⁷ , R ⁸ and R ⁹ . Where R
^{2-2a, R 3-2a, R 4-2a,} R 5-2a, R 6-2a, R 7-2a, R
^{Neither 8-2a nor} R ^9-2a represents a -COOH group or a group containing them, and the other symbols have the same meanings as described above. In the compound represented by the formula (1), among the compounds produced by the general formula (I-1), the R ¹ group represents a COOH group, and R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ and compounds which either does not represent a -COOH group or a group containing it in R ⁹ groups, namely general formula (I-1d)

Embedded image (Wherein all symbols have. As defined above) The compound of the general formula _{(IV) H 2 N-OR} 10 (IV) represented by (wherein, R ¹⁰ are as defined above.) Alternatively, a compound represented by the general formula (V) H ₂ N-NHR ¹⁰ (V) (wherein R ¹⁰ has the same meaning as described above) is subjected to an amidation reaction, and if necessary, an alkali It can be produced by subjecting to hydrolysis under conditions and / or deprotection under acid conditions and / or deprotection by hydrogenolysis. The amidation reaction, hydrolysis under alkaline conditions, deprotection reaction under acid conditions, and deprotection reaction by hydrogenolysis are known and are carried out by the methods described above.

(B) R ¹ is -CONHOR ¹⁰ or -C
ONHNHR ¹⁰ and R ² , R ³ , R ⁴ , R ⁵ , R
⁶ , a compound in which at least one of the groups R ⁷ , R ⁸ and R ⁹ represents a —COOH group or a group containing the same;
That is, the general formula (I-2b)

Embedded image ( ^Wherein , R ^2-2b , R ^3-2b , R ^4-2b , R ^5-2b , R ^6-2b , R
^7-2b, R ^8-2b, each ^{R 9-2b R 2, R 3,} R 4, R 5,
It has the same meaning as R ⁶ , R ⁷ , R ⁸ and R ⁹ . Where R
^{2-2b, R 3-2b, R 4-2b,} R 5-2b, R 6-2b, R 7-2b, R
^Among the groups ^8-2b and ^R9-2b , at least one group represents a -COOH group or a group containing them, and other symbols have the same meanings as described above. The compound represented by the formula (I-2a) is a compound in which the -COOH group or a group containing them is protected, that is, the compound represented by the formula (I-a).
2a1)

Embedded image ( ^Wherein R ^2-2a1 , R ^3-2a1 , R ^4-2a1 , R ^5-2a1 , R
^6-2a1 , R ^7-2a1 , R ^8-2a1 and R ^9-2a1 are each R ² ,
It has the same meaning as R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , and R ⁹ . However, R ^2-2a1 , R ^3-2a1 , R ^4-2a1 , R ^5-2a1 , R
^6-2a1, R ^7-2a1, at least one -COOH group group is protected out in ^{R 8-2a 1,} R 9-2a1 group (e.g., methyl group, ethyl group, t- butyl group and benzyl Group) or a group containing them, and the other symbols have the same meanings as described above. ) Can be produced by subjecting the compound represented by the formula (1) to alkali hydrolysis, deprotection under acidic conditions or deprotection by hydrogenolysis. The hydrolysis under alkaline conditions, the deprotection reaction under acid conditions, and the deprotection reaction by hydrogenolysis are known and are carried out by the methods described above.

[3] Among the compounds of the present invention represented by the general formula (I), the compound wherein R ¹ is — (CH ₂ ) _n SR ^50, that is, the compound of the general formula (I-3)

Embedded image (Wherein, R ^1-3 is -. (CH ₂₎ represents an _n SR ^50, and the other symbols represent the same meanings as described above), a compound represented by the
It can be manufactured by the following methods (a) and (b).

(A) R¹Is-(CH_Two)_nSR⁵⁰Represents
And R^Two, R^Three, R^Four, R^Five, R⁶, R ⁷, R⁸And R⁹
In any of the groups, a -COOH group or a group containing the group
A compound not represented, that is, a compound of the general formula (I-3a)

Embedded image (Wherein, R ^2-3a , R ^3-3a , R ^4-3a , R ^5-3a , R ^6-3a , R
^7-3a, R ^8-3a, each ^{R 9-3a R 2, R 3,} R 4, R 5,
It has the same meaning as R ⁶ , R ⁷ , R ⁸ and R ⁹ . Where R
^{2-3a, R 3-3a, R 4-3a,} R 5-3a, R 6-3a, R 7-3a, R
^{Neither 8-3a nor} R ^9-3a represents a —COOH group or a group containing them, and the other symbols have the same meanings as described above. The compound represented by the general formula (V)
I)

Embedded image (Wherein X represents a halogen atom, and the other symbols have the same meanings as described above), and a compound represented by the general formula (VII) R ⁵⁰¹ SK (VII) (wherein R ⁵⁰¹ represents C1-8 Alkyl group, -COR ⁵² ,-
SR ⁵³¹ (wherein, R ⁵³¹ represents a C1-8 alkyl group or a phenyl group). Can be produced by reacting the compound of the formula (1).

When R ⁵⁰ is a compound representing a hydrogen atom or —SH, the compound can be produced by subsequently subjecting the compound obtained above to a deprotection reaction.
The above reaction is known, for example, an organic solvent (acetone,
In tetrahydrofuran) by refluxing. Further, the subsequent deprotection reaction is known, for example, in an organic solvent (methanol, tetrahydrofuran, dioxane, etc.), an alkali metal hydroxide (sodium hydroxide, potassium hydroxide, lithium hydroxide, etc.),
The reaction is carried out at a temperature of 0 to 40 ° C. using a hydroxide (barium hydroxide, calcium hydroxide, etc.) or carbonate (sodium carbonate, potassium carbonate, etc.) of alkaline earth metal or an aqueous solution thereof or a mixture thereof.

(B) R¹Is-(CH_Two)_nSR⁵⁰Represents
And R^Two, R^Three, R^Four, R^Five, R⁶, R ⁷, R⁸And R⁹
At least one of the groups is a -COOH group or
A compound representing a group containing the compound represented by the general formula (I-
3b)

Embedded image ( ^Wherein , R ^2-3b , R ^3-3b , R ^4-3b , R ^5-3b , R ^6-3b , R
^7-3b, R ^8-3b, each ^{R 9-3b R 2, R 3,} R 4, R 5,
It has the same meaning as R ⁶ , R ⁷ , R ⁸ and R ⁹ . Where R
^2-3b , ^R3-3b , ^R4-3b , ^R5-3b , ^R6-3b , ^R7-3b , R
^{In the} groups ^8-3b and ^R9-3b , at least one group represents a -COOH group or a group containing them, and other symbols have the same meanings as described above. The compound represented by the general formula (I-3a) is a compound in which the -COOH group or a group containing them is protected, that is, the compound represented by the general formula (I-
3a1)

Embedded image ( ^Where R ^2-3a1 , R ^3-3a1 , R ^4-3a1 , R ^5-3a1 , R
^6-3a1 , R ^7-3a1 , R ^8-3a1 , and R ^9-3a1 are R ² ,
It has the same meaning as R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , and R ⁹ . However, R ^2-3a1 , R ^3-3a1 , R ^4-3a1 , R ^5-3a1 , R
^6-3a1, R ^7-3a1, at least one -COOH group group is protected out in ^{R 8-3a 1,} R 9-3a1 group (e.g., methyl group, ethyl group, t- butyl group and benzyl Group) or a group containing them, and the other symbols have the same meanings as described above. ) Can be produced by subjecting the compound represented by the formula (1) to alkali hydrolysis, deprotection under acidic conditions or deprotection by hydrogenolysis. The hydrolysis under alkaline conditions, the deprotection reaction under acid conditions, and the deprotection reaction by hydrogenolysis are known and are carried out by the methods described above.

[0183] [4] of the general formula (I) compound of the present invention represented by, compounds wherein R ¹ is ^{-Y-PO (OR 5 1)} 2,
That is, the general formula (I-4)

Embedded image (Wherein, R ^1-4 represents _{^{-Y-PO (OR 51) 2}} , and other symbols. Of the same meanings as defined above), a compound represented by the method of the following (a) ~ (d) It can be manufactured by

[0184] (a) R ¹ is a _{^{-Y 1 -PO (OR 51) 2}} ( in group, Y ¹ represents -O-, the other symbols have the same meanings as described above.) Represents and R ² , R ³ , R ⁴ ,
R ⁵ , R ⁶ , R ⁷ , R ⁸ and R ⁹ each represent —COO
A compound not representing an H group or a group containing the same, that is, a compound of the general formula (I-4a)

Embedded image ( ^Wherein , R ^2-4a , R ^3-4a , R ^4-4a , R ^5-4a , R ^6-4a , R
^7-4a , R ^8-4a and R ^9-4a are each R ² , R ³ , R ⁴ , R ⁵ ,
It has the same meaning as R ⁶ , R ⁷ , R ⁸ and R ⁹ . Where R
^2-4a , ^R3-4a , ^R4-4a , ^R5-4a , ^R6-4a , ^R7-4a , R
^{Neither 8-4a nor} R ^9-4a represents a -COOH group or a group containing them, and other symbols have the same meanings as described above. The compound represented by the general formula (VI)
II)

Embedded image (Wherein all symbols have the same meanings as described above), and a compound represented by the general formula (IX):

Embedded image (Wherein, R ⁵¹¹ represents a C1-8 alkyl group, a phenyl group or a known phosphoric acid protecting group, and the other symbols have the same meanings as described above). If protected, it can be produced by a subsequent deprotection reaction. The above reaction is known, for example, in an organic solvent (such as pyridine)
The reaction is carried out at 0 to 40 ° C. Further, the deprotection reaction of the protecting group of phosphoric acid is known, for example, by using zinc acetic acid in an organic solvent (pyridine or the like) at 0 to 40 ° C.
The reaction is performed by

(B) R ¹ represents -Y ¹ -PO (OR ⁵¹ ) ₂ , and among R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ and R ^9, A compound in which at least one group represents a -COOH group or a group containing the same, that is, a compound represented by the general formula (I-4b)

Embedded image ( ^Wherein , R ^2-4b , R ^3-4b , R ^4-4b , R ^5-4b , R ^6-4b , R
^7-4b , R ^8-4b and R ^9-4b represent R ² , R ³ , R ⁴ , R ⁵ ,
It has the same meaning as R ⁶ , R ⁷ , R ⁸ and R ⁹ . Where R
^2-4b , ^R3-4b , ^R4-4b , ^R5-4b , ^R6-4b , ^R7-4b , R
^{In the} groups ^8-4b and ^R9-4b , at least one group represents a -COOH group or a group containing them, and the other symbols have the same meanings as described above. The compound represented by the formula (I-4a) is a compound in which the -COOH group or a group containing the compound is protected, that is, the compound represented by the formula (I-a).
4a1)

Embedded image ( ^Where R ^2-4a1 , R ^3-4a1 , R ^4-4a1 , R ^5-4a1 , R
^6-4a1 , R ^7-4a1 , R ^8-4a1 and R ^9-4a1 are each R ² ,
It has the same meaning as R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , and R ⁹ . However, R ^2-4a1 , R ^3-4a1 , R ^4-4a1 , R ^5-4a1 , R
^6-4a1, R ^7-4a1, at least one -COOH group group is protected out in ^R 8-4a ^1, R 9-4a1 group (e.g., methyl group, ethyl group, t- butyl group and benzyl Group) or a group containing them, and the other symbols have the same meanings as described above. ) Can be produced by subjecting the compound represented by the formula (1) to alkali hydrolysis, deprotection under acidic conditions or deprotection by hydrogenolysis. The hydrolysis under alkaline conditions, the deprotection reaction under acid conditions, and the deprotection reaction by hydrogenolysis are known and are carried out by the methods described above.

(C) R ¹ represents -Y ² -PO (OR ⁵¹ ) ₂ (wherein Y ² represents a single bond or -CH _2- , and other symbols have the same meanings as described above). And a compound in which none of R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ and R ⁹ represents a —COOH group or a group containing the same, that is, a compound represented by the general formula (I- 4c)

Embedded image ( ^Wherein , R ^2-4c , R ^3-4c , R ^4-4c , R ^5-4c , R ^6-4c , R
^7-4c , R ^8-4c and R ^9-4c represent R ² , R ³ , R ⁴ , R ⁵ ,
It has the same meaning as R ⁶ , R ⁷ , R ⁸ and R ⁹ . Where R
^2-4c , ^R3-4c , ^R4-4c , ^R5-4c , ^R6-4c , ^R7-4c , R
^{None of} the groups ^8-4c and ^R9-4c represent a -COOH group or a group containing them, and the other symbols have the same meanings as described above. The compound represented by the general formula (X)

Embedded image (Wherein all symbols have the same meanings as described above) and a compound represented by the general formula (XI) or (XII) (R ⁵¹¹ O) ₃ P (XI) (R ⁵¹¹ O) ₂ POK (XII (Wherein all symbols have the same meanings as described above), and when phosphoric acid is protected, it can be produced by subsequent deprotection reaction. . The above reaction is known, and is carried out, for example, by reacting at 0 to 120 ° C. in an organic solvent (tetrahydrofuran, dimethylformamide, etc.). The phosphate group deprotection reaction is known and is carried out by the method described above.

(D) R ¹ represents -Y ² -PO (OR ⁵¹ ) ₂ , and among R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ and R ^9, A compound in which at least one group represents a -COOH group or a group containing the same, that is, a compound represented by the general formula (I-4d)

Embedded image ( ^Wherein , R ^2-4d , R ^3-4d , R ^4-4d , R ^5-4d , R ^6-4d , R
^7-4d, R ^8-4d, each ^{R 9-4d R 2, R 3,} R 4, R 5,
It has the same meaning as R ⁶ , R ⁷ , R ⁸ and R ⁹ . Where R
^2-4d , ^R3-4d , ^R4-4d , ^R5-4d , ^R6-4d , ^R7-4d , R
^At least one of the groups ^8-4d and ^R9-4d represents a -COOH group or a group containing them, and the other symbols have the same meanings as described above. The compound represented by the general formula (I-4c) is a compound in which the -COOH group or a group containing them is protected, that is, the compound represented by the general formula (I-c).
4c1)

Embedded image ( ^Wherein , R ^2-4c1 , R ^3-4c1 , R ^4-4c1 , R ^5-4c1 , R
^6-4c1 , R ^7-4c1 , R ^8-4c1 , and R ^9-4c1 are each R ² ,
It has the same meaning as R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , and R ⁹ . However, R ^2-4c1 , R ^3-4c1 , R ^4-4c1 , R ^5-4c1 , R
^6-4c1, R ^7-4c1, at least one -COOH group group is protected out in ^R 8-4c ^1, R 9-4c1 group (e.g., methyl group, ethyl group, t- butyl group and benzyl Group) or a group containing them, and the other symbols have the same meanings as described above. ) Can be produced by subjecting the compound represented by the formula (1) to alkali hydrolysis, deprotection under acidic conditions or deprotection by hydrogenolysis.

The hydrolysis under alkaline conditions, the deprotection reaction under acid conditions, and the deprotection reaction by hydrogenolysis are known and are carried out by the methods described above. In the present invention, the deprotection reaction means a general deprotection reaction that can be easily understood by those skilled in the art, such as alkali hydrolysis, deprotection reaction under acidic conditions, and deprotection reaction by hydrogenolysis. By properly using the reaction, the desired compound of the present invention can be easily produced.

As will be readily understood by those skilled in the art, examples of the carboxyl-protecting group include a methyl group, an ethyl group, a t-butyl group and a benzyl group. The group is not particularly limited as long as it can be eliminated. For example, TWGreene, Protective Gro
Ups in Organic Synthesis, Wiley, New York, 1991.

Examples of the hydroxyl-protecting group include a methoxymethyl group, a tetrahydropyranyl group, a t-butyldimethylsilyl group, an acetyl group and a benzyl group, and other groups which can be easily and selectively eliminated. There is no particular limitation as long as it exists. For example, TW Greene, Protective Groups
Those described in Organic Synthesis, Wiley, New York, 1991 are used.

Examples of the amino-protecting group include a benzyloxycarbonyl group, a t-butoxycarbonyl group, and a trifluoroacetyl group, and any other groups that can be easily and selectively eliminated can be used. Not done. For example, TW Greene, Protective Groups in Organic Sy
nthesis, Wiley, New York, 1991.

Formula (II), Formula (III), Formula (I
V), general formula (V), general formula (VI), general formula (VII), general formula (VIII), general formula (IX), general formula (X), general formula (XI), or general formula (XII) The compounds of the formula (1) are known per se or can be easily produced by known methods.

In each reaction in the present specification, the reaction product is purified by a conventional purification means, for example, distillation under normal pressure or reduced pressure, high performance liquid chromatography using silica gel or magnesium silicate, thin layer chromatography, or It can be purified by column chromatography or a method such as washing and recrystallization. Purification may be performed for each reaction or may be performed after completion of several reactions.

[0194]

[Pharmacological activity of the compound of the present invention] The following experiment proved that the compound of the present invention represented by the general formula (I) has a matrix metalloproteinase inhibitory activity.

(1) Gelatinase A inhibitory activity [Experimental method] 10 mM p-aminophenylmercuric acetate (10 μm) was added to an assay buffer (40 μl) solution of progelatinase A (5 μl) purified from human normal skin fibroblasts (HNDF). APMA) (5 μl)
Pre-incubation at 37 ° C. for 1 hour activated the enzyme. Synthetic substrate (MOCAc-Pro-Leu-Gly-A2pr (Dnp) -Ala-
Arg-NH ₂ ) (130 μl; final concentration 13.5 μM) and various concentrations of test compound solutions or solutions without test compound addition (20 μl) were preincubated at 37 ° C. for 5 minutes. The activated enzyme prepared above (50 μl / well) was added thereto, and the mixture was incubated at 37 ° C. for 15 minutes to start the enzyme reaction. Enzyme activity was determined by the fluorescence intensity per minute [325 nm (Ex) / 393 nm].
(Em)]. The inhibitory activity was expressed as an inhibition rate (%) with respect to the enzyme activity when no test compound was added. For example, the compound of Example 71 has an IC ₅₀ value of 0.
50 nM.

(2) Collagenase inhibitory activity [Experimental method] 1 mg / ml trypsin (45 μl) was added to an assay buffer (105 μl) solution of procollagenase (5 μl) purified from human normal skin fibroblasts (HNDF). The enzyme was activated by preincubation at 37 ° C. for 1 minute. 5 mg /
ml of soybean trypsin inhibitor
tor) (SBTI; 50 μl) was added to inactivate trypsin. Synthetic substrate (Ac-Pro-Leu-Gly- [2-mercapto
4-methyl-pentanoyl] -Leu-Gly-OEt) (105 μl; final concentration 1.33 mM) and various concentrations of test compound solutions or solutions (20 μl) to which test compounds were not added were added.
Preincubation was performed at 6 ° C for 5 minutes. There, the activated enzyme prepared above (75 μl / tube, 50 μl)
Was added and incubated at 26 ° C. for 10 minutes.
During the 10 minutes, a total of 40 points of the absorbance at 324 nm were measured, and Vmax at 30 points was measured. For example, the compound of Example 71 has an IC ₅₀ value of 2.
5 μM.

(3) Stromlysin inhibitory activity [Experimental method] 9 volumes of human stromlysin (Yagai) were added to 10 mM p-aminophenylmercury acetate (APM).
A) It was mixed with 1 volume and activated at 37 ° C. for 20 hours. Assay buffer (50 mM Tris-HCl, 10 mM CaCl ₂ , 0.05% B
rij35, 0.02% NaN ₃ (pH 7.5)) 10 μl of a test compound dissolved in 150 μl of dimethyl sulfoxide and a synthetic substrate NFF-3 (Mca-Arg-Pro-Lys-Pro-Val-Glu-Nva-Trp-Ar
g-Lys (DNP) -NH ₂ , Nva: norvaline, Institute for Peptide Research
Of 10 mM dimethyl sulfoxide solution in water with 0.5 mM
After adding 10 μl of the purified solution, further adding 30 μl of assay buffer and incubating at 37 ° C. for 10 minutes, the activated stromlysin solution (50 μl) was added.
1 was added to start the enzymatic reaction. The enzyme activity was represented by the increase in the fluorescence intensity [325 nm (Ex) / 393 nm (Em)] per minute. The inhibitory activity was expressed as an inhibition rate (%) with respect to the enzyme activity when no test compound was added. For example, the compound of Example 71 had an IC ₅₀ value of 26 nM.

[0198]

[Toxicity] The toxicity of the compound of the present invention is very low,
It can be determined that it is safe enough for use as a medicine.

[0199]

[Application to pharmaceuticals] In animals including humans, particularly humans, inhibition of matrix metalloproteinases such as gelatinase, stromlysin or collagenase, etc., results in rheumatism, osteoarthritis, pathological bone resorption, osteoporosis, periodontal disease, Interstitial nephritis, arteriosclerosis, emphysema, cirrhosis, corneal injury, metastatic invasion and proliferation of cancer cells, autoimmune diseases (such as Crohn's disease and Shugren's disease), diseases caused by vascular migration and infiltration of leukocyte cells, It is useful for the prevention and / or treatment of angiogenesis, multiple sclerosis, aortic aneurysm, endometriosis and the like.

In order to use the compound of the present invention represented by the general formula (I), a non-toxic salt, an acid addition salt, or a hydrate thereof for the above-mentioned purpose, it is usually used systemically or locally, orally or orally. It is administered in parenteral form.

The dose is determined based on the age, body weight, symptoms, therapeutic effect,
Depending on the administration method, treatment time, etc., it is usually 1 mg to 1000 mg per adult per dose.
Administered orally once to several times a day, or parenterally (preferably intravenously) once to several times a day in a range of 1 mg to 100 mg per adult per person; Alternatively, it is continuously administered intravenously for 1 hour to 24 hours a day. Of course, as described above, the dose varies depending on various conditions, so that a dose smaller than the above-mentioned dose may be sufficient, or may be required beyond the range.

When the compound of the present invention is administered, it is used as a solid composition, a liquid composition and other compositions for oral administration and an injection, an external preparation, a suppository and the like for parenteral administration. Solid compositions for oral administration include tablets, pills, capsules, powders, granules and the like. Capsules include hard capsules and soft capsules.

In such a solid composition, the one or more active substances comprise at least one inert diluent such as lactose, mannitol, glucose, hydroxypropylcellulose, microcrystalline cellulose, starch, polyvinylpyrrolidone, It is mixed with magnesium metasilicate aluminate. The composition may contain, in a conventional manner, additives other than an inert diluent, for example, a lubricant such as magnesium stearate, a disintegrant such as calcium cellulose glycolate, a stabilizer such as lactose, glutamic acid or asparagine. A solubilizing agent such as an acid may be contained. The tablet or pill may be coated with a film of a gastric or enteric substance such as sucrose, gelatin, hydroxypropylcellulose, hydroxypropylmethylcellulose phthalate, or may be coated with two or more layers, if necessary. . Also included are capsules of absorbable materials such as gelatin.

[0204] Liquid compositions for oral administration include pharmaceutically acceptable emulsions, solutions, syrups, elixirs and the like. In such liquid compositions, one or more active substances are contained in commonly used inert diluents (eg, purified water, ethanol). The composition may contain, in addition to the inert diluent, adjuvants such as wetting agents and suspending agents, sweetening agents, flavoring agents, fragrances, and preservatives.

Other compositions for oral administration include sprays which contain one or more active substances and are formulated in a manner known per se. This composition contains, in addition to the inert diluent, buffers such as sodium bisulfite, which provide isotonicity with stabilizers, e.g., isotonic agents such as sodium chloride, sodium citrate, or citric acid. You may. The method of producing the spray is described, for example, in U.S. Pat.
It is described in detail in 3,095,355.

Injections for parenteral administration according to the present invention include sterile aqueous or non-aqueous solutions, suspensions, and emulsions. Aqueous solutions and suspensions include, for example, distilled water for injection and physiological saline. Examples of the water-insoluble solutions and suspensions include propylene glycol, polyethylene glycol, vegetable oils such as olive oil, alcohols such as ethanol, and Polysorbate 80 (registered trademark). Such compositions may also contain adjuvants such as preserving, wetting, emulsifying, dispersing, stabilizing (eg, lactose) and solubilizing agents (eg, glutamic acid, aspartic acid). . These are sterilized by filtration through a bacteria retaining filter, blending of a bactericide or irradiation. They can also be used to produce sterile solid compositions, for example, sterilized or dissolved in sterile distilled water for injection or other solvents before use of the lyophilized product.

Other compositions for parenteral administration include external solutions, ointments, liniments, suppositories and suppositories for rectal administration, which contain one or more active substances and are formulated in a conventional manner. Pessaries for vaginal administration are included.

[0208]

EXAMPLES The present invention will now be described in detail with reference to Examples and Examples, but the present invention is not limited thereto. Chromatographic separation point and TLC
The solvent in parentheses shown in the above indicates the elution solvent or developing solvent used, and the ratio indicates the volume ratio. The solvent in parentheses shown in the NMR section indicates the solvent used for the measurement.

Reference Example 1 2- (dihydroxyboronyl) benzofuran

Embedded image Benzofuran (128 g) in tetrahydrofuran (54
0 ml) solution in a dry ice-methanol bath,
1.6N n-butyllithium hexane solution (750m
l) was added dropwise. After stirring the reaction mixture at 0 ° C. for 30 minutes, triisopropyl borate (275 ml) was added dropwise under cooling with a dry ice-methanol bath. The reaction mixture was stirred at 0 ° C. for 1 hour. Concentrate the reaction mixture and add 1 to the residue.
An N hydrochloric acid aqueous solution was added, and the mixture was extracted with ethyl acetate. The extract was washed with water and a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and concentrated. The obtained crystals were washed with hexane and dried, and the title compound (1) having the following physical data was obtained.
57 g) were obtained. TLC: Rf 0.28 (n-hexane: ethyl acetate = 1:
1).

Reference Example 2 Ethyl 4- (benzofuran-2-yl) benzoate

Embedded image In a solution of 4-iodobenzoic acid ethyl ester (5 g) in dimethylformamide (10 ml), the compound (2.64 g) produced in Reference Example 1 and dichlorobis (triphenylphosphine) palladium (II) [PdCl ₂ (PPh ₃ ) ₂ ] ( 0.6
35 g) and triethylamine (10 ml) were added. The reaction mixture was stirred at 80 C for 6 hours. A 1N aqueous hydrochloric acid solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate and concentrated. The obtained crystals were washed with hexane / diethyl ether and dried to give the title compound (3.6 g) having the following physical data. TLC: Rf 0.61 (n-hexane: ethyl acetate = 9:
1).

Reference Example 3 4- (benzofuran-2-yl) benzoic acid

Embedded image The compound (3.4 g) prepared in Reference Example 2 was treated with dioxane (1
5N) solution at room temperature with 1N aqueous sodium hydroxide solution (1
5.3 ml) was added. The reaction mixture was stirred at room temperature for 9 hours. A 1N aqueous hydrochloric acid solution was added to the reaction mixture until it became acidic, and the mixture was extracted with ethyl acetate: tetrahydrofuran (2: 1). The extract was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate and concentrated. The obtained crystals were washed with ethyl acetate / diethyl ether and dried to give the title compound (2.1 g) having the following physical data. TLC: Rf 0.43 (chloroform: methanol: acetic acid = 100: 10: 1).

Reference Example 4 4- (benzofuran-2-yl) benzoyl chloride

Embedded image A mixture of the compound (13.4 g) produced in Reference Example 3 and thionyl chloride (80 ml) was stirred at 80 ° C. for 6 hours. The reaction mixture was cooled to room temperature and concentrated. The obtained residue was washed with hexane / diethyl ether to give the title compound (12.7 g) having the following physical data. NMR (CDCl ₃ ): δ 8.19 (2H, d, J = 8.8 Hz), 7.98
(2H, d, J = 8.8Hz), 7.68-7.61 (1H, m), 7.59-7.53 (1
H, m), 7.42-7.23 (3H, m).

Example 1 Ethyl 4- (N- (4- (benzofuran-2-yl) phenylcarbonyl) amino) butanoate

Embedded image To a solution of ethyl 4-aminobutanoate (0.5 g) in dichloromethane (20 ml) was added triethylamine (1 m).
l) was added. To the mixture was added a solution of the compound prepared in Reference Example 4 (0.72 g) in dichloromethane (10 ml) at 0 ° C. The reaction mixture was stirred at room temperature for 30 minutes. A 1N aqueous hydrochloric acid solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate and concentrated. The obtained residue was washed with ethyl acetate / diethyl ether and dried to give the title compound (0.732 g) having the following physical data. TLC: Rf 0.38 (n-hexane: ethyl acetate = 1:
1).

Example 2 4- (N- (4- (benzofuran-2-yl) phenylcarbonyl) amino) butanoic acid

Embedded image To a solution of the compound prepared in Example 1 (670 mg) in tetrahydrofuran (5 ml) was added a 1N aqueous sodium hydroxide solution (4.4 ml). The reaction mixture was stirred at room temperature for 3 hours. A 1N aqueous hydrochloric acid solution was added to the reaction mixture until it became acidic, and the mixture was extracted with ethyl acetate / tetrahydrofuran. The extract was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate and concentrated to give the title compound (0.617 g) having the following physical data. TLC: Rf 0.40 (chloroform: methanol: acetic acid = 100: 10: 1); NMR (CD ₃ OD): δ 8.58 (1H, t, J = 5.6 Hz), 8.01
(2H, d, J = 8.8Hz), 7.96 (2H, d, J = 8.8Hz), 7.71-7.63
(2H, m), 7.57 (1H, d, J = 0.8Hz), 7.39-7.23 (2H, m),
3.32-3.25 (2H, m), 2.29 (2H, t, J = 7.6Hz), 1.84-1.
70 (2H, m).

Examples 2 (1) to 2 (24) Using the corresponding acid halide in place of the compound prepared in Reference Example 4, operating in the same manner as in Example 1 → Example 2, Was obtained.

Example 2 (1) 4- (N- (4-methylphenylcarbonyl) amino)
Butanoic acid

Embedded image TLC: Rf 0.50 (chloroform: methanol: acetic acid = 18: 2: 1); NMR (CD ₃ OD): δ 12.10 (1H, brs), 8.30 (1H, t,
J = 5.5Hz), 7.76 (2H, d, J = 8.0Hz), 7.28 (2H, d, J = 8.
0Hz), 3.30 (2H, m), 2.30 (2H, t, J = 7.2Hz), 1.75 (2
H, m).

Example 2 (2) 4- (N- (4-butyloxyphenylcarbonyl) amino) butanoic acid

Embedded image TLC: Rf 0.48 (chloroform: methanol: acetic acid = 18: 2: 1); NMR (d ₆ -DMSO): δ 12.03 (1H, brs), 8.29 (1H,
t, J = 5.5Hz), 7.78 (2H, d, J = 8.8Hz), 6.95 (2H, d, J
= 8.8Hz), 3.99 (2H, t, J = 6.4Hz), 3.30-3.14 (2H, m),
2.24 (2H, t, J = 7.6Hz), 1.79-1.62 (4H, m), 1.51-1.3
2 (2H, m), 0.91 (3H, t, J = 7.4Hz).

Example 2 (3) 4- (N- (3-butyloxyphenylcarbonyl) amino) butanoic acid

Embedded image TLC: Rf 0.58 (chloroform: methanol: acetic acid = 18: 2: 1); NMR (d ₆ -DMSO): δ 12.04 (1H, brs), 8.42 (1H,
t, J = 5.4Hz), 7.41-7.28 (3H, m), 7.07-7.00 (1H, m),
3.99 (2H, t, J = 6.4Hz), 3.24 (2H, m), 2.25 (2H, t,
J = 7.3Hz), 1.80-1.64 (4H, m), 1.42 (2H, m), 0.92 (3
H, t, J = 7.3Hz).

Example 2 (4) 4- [N- [4- (2- (4-methylphenyl) ethynyl) furan-2-ylcarbonyl] amino] butanoic acid

Embedded image TLC: Rf 0.54 (chloroform: methanol: acetic acid = 18: 2: 1); NMR (d ₆ -DMSO): δ 12.07 (1H, brs), 8.51 (1H,
t, J = 6.0Hz), 7.44 (2H, d, J = 8.1Hz), 7.25 (2H, d, J
= 8.1Hz), 7.12 (1H, d, J = 3.7Hz), 6.94 (1H, d, J = 3.7H
z), 3.26-3.23 (2H, m), 2.33 (3H, s), 2.23 (2H, d,
J = 7.5Hz), 1.79-1.63 (2H, m).

Example 2 (5) 4- (N- (4- (pyrrol-1-yl) phenylcarbonyl) amino) butanoic acid

Embedded image TLC: Rf 0.59 (chloroform: methanol: acetic acid = 18: 2: 1); NMR (d ₆ -DMSO): δ 12.04 (1H, brs), 7.94 (2H,
d, J = 8.8Hz), 7.66 (2H, d, J = 8.8Hz), 7.47-7.44 (2H,
m), 6.31-6.28 (2H, m), 3.32-3.25 (2H, m), 2.29 (2
H, t, J = 7.3Hz), 1.77 (2H, m).

Example 2 (6) 4- (N- (trans-4-methylcyclohexylcarbonyl) amino) butanoic acid

Embedded image TLC: Rf 0.55 (chloroform: methanol: acetic acid = 18: 2: 1); NMR (d ₆ -DMSO): δ 12.01 (1H, brs), 7.67 (1H,
t, J = 6.0Hz), 3.02 (2H, m), 2.19 (2H, t, J = 7.5Hz),
2.06-1.91 (1H, m), 1.74-1.52 (6H, m), 1.46-1.18 (4
H, m), 0.98-0.76 (4H, m).

Example 2 (7) 4- (N- (4- (3-methoxy-1-propynyl) phenylcarbonyl) amino) butanoic acid

Embedded image TLC: Rf 0.45 (chloroform: methanol: acetic acid = 18: 2: 1); NMR (d ₆ -DMSO): δ 12.03 (1H, brs), 8.54 (1H,
t, J = 5.3Hz), 7.85 (2H, d, J = 8.2Hz), 7.52 (2H, d, J
= 8.2Hz), 4.34 (2H, s), 3.35 (3H, s), 3.34-3.22 (2
H, m), 2.28 (2H, t, J = 7.0Hz), 1.76 (2H, m).

Example 2 (8) 4- (N- (4-butylphenylcarbonyl) amino)
Butanoic acid

Embedded image TLC: Rf 0.54 (chloroform: methanol: acetic acid = 18: 2: 1); NMR (CD ₃ OD): δ 12.03 (1H, brs), 8.37 (1H, t,
J = 5.5Hz), 7.75 (2H, d, J = 8.2Hz), 7.25 (2H, d, J = 8.
2Hz), 3.33-3.22 (2H, m), 2.62 (2H, t, J = 7.5Hz), 2.
27 (2H, t, J = 7.4Hz), 1.83-1.67 (2H, m), 1.65-1.48
(2H, m), 1.40-1.22 (2H, m), 0.90 (3H, t, J = 7.1H
z).

Example 2 (9) 4- (N- (benzofuran-2-ylcarbonyl) amino) butanoic acid

Embedded image TLC: Rf 0.32 (chloroform: methanol: acetic acid = 100: 10: 1); NMR (d ₆ -DMSO): δ 8.73 (1H, t, J = 5.4 Hz), 7.78
-7.73 (1H, m), 7.66-7.61 (1H, m), 7.51 (1H, d, J =
0.8Hz), 7.49-7.41 (1H, m), 7.36-7.28 (1H, m), 3.28
(2H, m), 2.27 (2H, t, J = 7.4Hz), 1.83-1.68 (2H,
m).

Example 2 (10) 4- [N- [4- (2- (4-chlorophenyl) ethenyl) phenylcarbonyl] amino] butanoic acid

Embedded image TLC: Rf 0.28 (chloroform: methanol = 1
0: 1); NMR (d ₆ -DMSO): δ 8.48 (1H, t, J = 5.6Hz), 7.85
(2H, d, J = 8.4Hz), 7.67 (2H, d, J = 8.4Hz), 7.65 (2
H, d, J = 8.8Hz), 7.44 (2H, d, J = 8.8Hz), 7.40 (1H, d,
J = 16.4Hz), 7.30 (1H, d, J = 16.4Hz), 3.27 (2H, m),
2.27 (2H, t, J = 7.4Hz), 1.82-1.68 (2H, m).

Example 2 (11) 4- [N- [4- (2- (4- (imidazol-1-yl) phenyl) ethynyl) phenylcarbonyl] amino] butanoic acid

Embedded image TLC: Rf 0.29 (chloroform: methanol: acetic acid = 100: 10: 1); NMR (d ₆ -DMSO): δ 8.65 (1H, t, J = 5.4 Hz), 8.36
(1H, brs), 7.90 (2H, d, J = 8.4Hz), 7.84 (1H, brs),
7.77 (2H, d, J = 9.2Hz), 7.71 (2H, d, J = 9.2Hz), 7.6
5 (2H, d, J = 8.4Hz), 7.13 (1H, brs), 3.28 (2H, m),
2.31 (2H, t, J = 7.2Hz), 1.82-1.68 (2H, m).

Example 2 (12) 4- (N- (trans-4-propylcyclohexylcarbonyl) amino) butanoic acid

Embedded image TLC: Rf 0.65 (chloroform: methanol: acetic acid = 18: 2: 1); NMR (d ₆ -DMSO): δ 12.00 (1H, s), 7.74-7.61 (1
H, t, J = 6.0Hz), 3.02 (2H, m), 2.19 (2H, t, J = 7.2H
z), 2.11-1.92 (1H, m), 1.78-1.53 (6H, m), 1.43-1.0
8 (7H, m), 0.95-0.89 (5H, m).

Example 2 (13) 4- [N- [4- (2- (4-methylphenyl) ethynyl) phenylcarbonyl] amino] butanoic acid

Embedded image TLC: Rf 0.57 (chloroform: methanol: acetic acid = 18: 2: 1); NMR (CD ₃ OD): δ 12.05 (1H, s), 8.57 (1H, t, J)
= 5.5Hz), 7.88 (2H, d, J = 8.3Hz), 7.61 (2H, d, J = 8.3
Hz), 7.47 (2H, d, J = 8.3Hz), 7.25 (2H, d, J = 8.3Hz),
3.34-3.24 (2H, m), 2.35 (3H, s), 2.29 (2H, t, J =
7.2Hz), 1.77 (2H, m).

Example 2 (14) 4- [N- [4-((4-bromophenyl) aminosulfonyl) phenylcarbonyl] amino] butanoic acid

Embedded image TLC: Rf 0.45 (chloroform: methanol: acetic acid = 18: 2: 1); NMR (d ₆ -DMSO): δ 12.03 (1H, brs), 10.53 (1H,
brs), 8.68-8.62 (1H, m), 7.95 (2H, d, J = 8.6Hz),
7.81 (2H, d, J = 8.6Hz), 7.42 (2H, d, J = 9.0Hz), 7.05
(2H, d, J = 9.0Hz), 3.33-3.21 (2H, m), 2.27 (2H, t,
J = 7.3Hz), 1.74 (2H, m).

Example 2 (15) 4- [N- (4-cyclohexylphenylcarbonyl)
Amino] butanoic acid

Embedded image TLC: Rf 0.33 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 12.04 (1H, s), 8.45-8.27 (1
H, m), 7.75 (2H, d, J = 8.4Hz), 7.28 (2H, d, J = 8.4H
z), 3.34-3.21 (2H, m), 2.64-2.44 (1H, m), 2.26 (2
H, t, J = 7.3Hz), 1.85-1.61 (7H, m), 1.56-1.19 (5H,
m).

Example 2 (16) 4- [N- [4- (4-propylphenyl) phenylcarbonyl] amino] butanoic acid

Embedded image TLC: Rf 0.32 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 12.05 (1H, s), 8.56-8.44 (1
H, m), 7.93 (2H, d, J = 8.4Hz), 7.73 (2H, d, J = 8.4H
z), 7.64 (2H, d, J = 8.4Hz), 7.30 (2H, d, J = 8.4Hz),
3.40-3.25 (2H, m), 2.61 (2H, t, J = 7.4Hz), 2.29 (2
H, t, J = 7.3Hz), 1.86-1.54 (4H, m), 0.92 (3H, t, J =
7.4Hz).

Example 2 (17) 4- [N- [4- (4-hydroxyphenyl) phenylcarbonyl] amino] butanoic acid

Embedded image TLC: Rf 0.17 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 12.05 (1H, s), 9.62 (1H,
s), 8.53-8.42 (1H, m), 7.89 (2H, d, J = 8.5Hz), 7.66
(2H, d, J = 8.2Hz), 7.56 (2H, d, J = 8.5Hz), 6.87 (2H,
d, J = 8.2Hz), 3.36-3.26 (2H, m), 2.29 (2H, t, J = 7.
2Hz), 1.77 (2H, m).

Example 2 (18) 4- [N- [4- (4-chlorophenyl) furan-2-
Ylcarbonyl] amino] butanoic acid

Embedded image TLC: Rf 0.24 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 12.07 (1H, s), 8.62-8.51 (1
H, m), 7.94 (2H, d, J = 8.4Hz), 7.54 (2H, d, J = 8.4H
z), 7.17-7.11 (2H, m), 3.33-3.22 (2H, m), 2.29 (2
H, t, J = 7.2Hz), 1.77 (2H, m).

Example 2 (19) 4- [N- [4- (4-heptylphenyl) phenylcarbonyl] amino] butanoic acid

Embedded image TLC: Rf 0.65 (chloroform: methanol: acetic acid = 18: 2: 1); NMR (d ₆ -DMSO): δ 12.04 (1H, s), 8.55-8.45 (1
H, m), 7.93 (2H, d, J = 8.4Hz), 7.73 (2H, d, J = 8.4H
z), 7.63 (2H, d, J = 8.4Hz), 7.29 (2H, d, J = 8.4Hz),
3.37-3.23 (2H, m), 2.62 (2H, t, J = 7.5Hz), 2.29 (2
(H, t, J = 7.1Hz), 1.78 (2H, m), 1.68-1.48 (2H, m), 1.
39-1.15 (8H, m), 0.86 (3H, t, J = 6.6Hz).

Example 2 (20) 4- [N- [4- (4-methoxyphenyl) phenylcarbonyl] amino] butanoic acid

Embedded image TLC: Rf 0.11 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 12.05 (1H, s), 8.55-8.45 (1
H, m), 7.91 (2H, d, J = 8.4Hz), 7.71 (2H, d, J = 8.4H
z), 7.68 (2H, d, J = 8.9Hz), 7.05 (2H, d, J = 8.9Hz),
3.81 (3H, s), 3.35-3.22 (2H, m), 2.29 (2H, t, J = 7.
3Hz), 1.76 (2H, m).

Example 2 (21) 4- [N- [4- (4-chlorophenyl) phenylcarbonyl] amino] butanoic acid

Embedded image NMR (d ₆ -DMSO): δ 12.07 (1H, s), 8.59-8.50 (1
H, m), 7.95 (2H, d, J = 8.4Hz), 7.81-7.71 (4H, m), 7.
54 (2H, d, J = 8.8Hz), 3.33-3.24 (2H, m), 2.29 (2H,
t, J = 7.3Hz), 1.82-1.71 (2H, m).

Example 2 (22) 4- [N- (5-benzyloxyindol-2-ylcarbonyl) amino] butanoic acid

Embedded image TLC: Rf 0.13 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 11.39 (1H, s), 8.42 (1H, t,
J = 5.6Hz), 7.50-7.20 (6H, m), 7.15 (1H, d, J = 2.2H
z), 6.99 (1H, d, J = 1.8Hz), 6.89 (1H, dd, J = 8.6, 2.
2Hz), 5.07 (2H, s), 3.27 (2H, m), 2.27 (2H, t, J =
7.4Hz), 1.73 (2H, m).

Example 2 (23) 4- [N- [5- (2- (4-chlorophenyl) ethenyl) furan-2-ylcarbonyl] amino] butanoic acid

Embedded image TLC: Rf 0.52 (chloroform: methanol: acetic acid: water = 100: 10: 1: 1); NMR (d ₆ -DMSO): δ 12.06 (1H, brs), 8.43 (1H,
t, J = 5.8Hz), 7.59 (2H, d, J = 8.8Hz), 7.42 (2H, d, J
= 8.8Hz), 7.26 (1H, d, J = 16.6Hz), 7.14 (1H, d, J = 16.
6Hz), 7.09 (1H, d, J = 3.2Hz), 6.63 (1H, d, J = 3.2H
z), 3.25 (2H, m), 2.26 (2H, t, J = 7.2Hz), 1.73 (2H,
m).

Example 2 (24) 4- [N- (4-phenoxyphenylcarbonyl) amino] butanoic acid

Embedded image TLC: Rf 0.47 (chloroform: methanol: acetic acid: water = 100: 10: 1: 1); NMR (d ₆ -DMSO): δ 8.41 (1H, t, J = 5.4 Hz), 7.85
(2H, d, J = 8.4Hz), 7.42 (2H, t, J = 8.0Hz), 7.18 (1
H, t, J = 7.2Hz), 6.97-7.08 (4H, m), 3.24 (2H, m),
2.25 (2H, t, J = 7.4Hz), 1.72 (2H, m).

Example 3 N- (1-methoxy-1,1-dimethylmethyl) oxy-4- (N- (4- (benzofuran-2-yl) phenylcarbonyl) amino) butyramide

Embedded image A solution of the compound (0.55 g) prepared in Example 2 in dimethylformamide (10 ml) was added to N- (1-methoxy-1,1
-Dimethylmethyloxy) amine (0.455 g), 1-hydroxybenzotriazole hydrate (0.391 g), 1
-Ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride (0.489 g) was added under ice-cooling,
Stirred for hours. Water was added to the reaction mixture, and extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium hydrogencarbonate and a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate and concentrated. The title compound having the following physical properties (0.23
0 g). TLC: Rf 0.13 (chloroform: methanol = 1
0: 1).

Example 4 N-hydroxy-4- (N- (4- (benzofuran-2)
-Yl) phenylcarbonyl) amino) butyramide

Embedded image To a solution of the compound prepared in Example 3 (0.230 g) in methanol (10 ml) was added a 1N aqueous hydrochloric acid solution (100 ml). The reaction mixture was stirred at room temperature for 10 minutes. The reaction mixture was concentrated, and the obtained residue was washed with diethyl ether to give the title compound (0.218 g) having the following physical data. TLC: Rf 0.22 (chloroform: methanol: acetic acid = 100: 10: 1); NMR (d ₆ -DMSO): δ 10.39 (1H, brs), 8.59 (1H,
t, J = 5.8Hz), 8.01 (2H, d, J = 9.0Hz), 7.96 (2H, d, J
= 9.0Hz), 7.67 (2H, m), 7.57 (1H, d, J = 0.5Hz), 7.39
-7.23 (2H, m), 3.27 (2H, q, J = 5.8Hz), 2.03 (2H, t,
J = 7.6Hz), 1.76 (2H, m).

Examples 4 (1) to 4 (36) In place of the compound prepared in Example 2, Examples 2 (1) to 4 (36)
Example 3 → Example 4 using the compound prepared in 2 (24) or a compound obtained by operating the same method as shown in Example 2 using the corresponding compound. The compound shown below was obtained in the same manner as described above.

Example 4 (1) N-hydroxy-4- (N- (4-methylphenylcarbonyl) amino) butyramide

Embedded image TLC: Rf 0.23 (chloroform: methanol = 1
0: 1); NMR (d ₆ -DMSO): δ 10.39 (1H, s), 8.70 (1H,
s), 8.40 (1H, t, J = 5.2Hz), 7.74 (2H, d, J = 8.1Hz),
7.25 (2H, d, J = 8.1Hz), 3.24 (2H, td, J = 6.6,5.2Hz),
2.35 (3H, s), 2.02 (2H, t, J = 7.7Hz), 1.74 (2H,
m).

Example 4 (2) N-hydroxy-4- (N- (4-butyloxyphenylcarbonyl) amino) butyramide

Embedded image TLC: Rf 0.29 (chloroform: methanol: acetic acid = 18: 2: 1); NMR (d ₆ -DMSO): δ 10.39 (1H, s), 8.70 (1H, br)
s), 8.32 (1H, t, J = 5.8Hz), 7.80 (2H, d, J = 9.0Hz),
6.96 (2H, d, J = 9.0Hz), 4.01 (2H, t, J = 6.4Hz), 3.35
-3.15 (2H, m), 2.01 (2H, t, J = 7.3Hz), 1.81-1.64 (4
H, m), 1.44 (2H, m), 0.94 (3H, t, J = 7.4Hz).

Example 4 (3) N-hydroxy-4- (N- (3-butyloxyphenylcarbonyl) amino) butyramide

Embedded image TLC: Rf 0.31 (chloroform: methanol: acetic acid = 18: 2: 1); NMR (d ₆ -DMSO): δ 10.39 (1H, s), 8.45 (1H, t,
J = 5.2Hz), 7.43-7.29 (3H, m), 7.19-7.01 (1H, m), 4.
01 (2H, t, J = 6.3Hz), 3.30-3.18 (2H, m), 2.02 (2H,
t, J = 7.5Hz), 1.83-1.64 (4H, m), 1.49 (2H, m), 0.95
(3H, t, J = 7.3Hz).

Example 4 (4) N-hydroxy-4- [N- [4-((4-methylphenyl) ethynyl) furan-2-ylcarbonyl] amino] butyramide

Embedded image TLC: Rf 0.32 (chloroform: methanol: acetic acid = 18: 2: 1); NMR (d ₆ -DMSO): δ 10.40 (1H, brs), 10.22 (1H,
s), 8.56 (1H, t, J = 5.7Hz), 7.47 (2H, d, J = 8.3Hz),
7.28 (2H, d, J = 8.3Hz), 7.16 (1H, d, J = 3.6Hz), 6.9
6 (1H, d, J = 3.6Hz), 3.28-3.14 (2H, m), 2.36 (3H,
s), 2.00 (2H, t, J = 7.5Hz), 1.83-1.64 (2H, m).

Example 4 (5) N-hydroxy-4- (N- (4- (pyrrol-1-yl) phenylcarbonyl) amino) butyramide

Embedded image TLC: Rf 0.31 (chloroform: methanol: acetic acid = 18: 2: 1); NMR (d ₆ -DMSO): δ 10.40 (1H, s), 9.00-8.24 (1
H, brs), 8.52 (1H, t, J = 5.6Hz), 7.94 (2H, d, J = 8.5
Hz), 7.68 (2H, d, J = 8.5Hz), 7.50-7.44 (2H, m), 6.34
-6.29 (2H, m), 3.38-3.31 (2H, m), 2.04 (2H, t, J =
7.5Hz), 1.76 (2H, m).

Example 4 (6) N-hydroxy-4- (N- (trans-4-methylcyclohexylcarbonyl) amino) butyramide

Embedded image TLC: Rf 0.29 (chloroform: methanol: acetic acid = 18: 2: 1); NMR (d ₆ -DMSO): δ 10.37 (1H, s), 10.20 (1H,
s), 7.69 (1H, t, J = 5.3Hz), 3.07-2.92 (2H, m), 2.31
-1.88 (3H, m), 1.74-1.52 (6H, m), 1.46-1.18 (3H, m
m), 0.98-0.76 (2H, m), 0.85 (3H, d, J = 6.6Hz).

Example 4 (7) N-hydroxy-4- (N- (4- (3-methoxy-1
-Propynyl) phenylcarbonyl) amino) butyramide

Embedded image TLC: Rf 0.32 (chloroform: methanol: acetic acid = 18: 2: 1); NMR (d ₆ -DMSO): δ 10.39 (1H, s), 8.57 (1H, t,
J = 5.5Hz), 7.85 (2H, d, J = 8.6Hz), 7.53 (2H, d, J = 8.
6Hz), 4.35 (2H, s), 3.35 (3H, s), 3.25 (2H, dt, J =
5.5, 7.2Hz), 2.02 (2H, t, J = 7.2Hz), 1.74 (2H, quin
t, J = 7.2Hz).

Example 4 (8) N-hydroxy-4- (N- (4-butylphenylcarbonyl) amino) butyramide

Embedded image TLC: Rf 0.37 (chloroform: methanol: acetic acid = 18: 2: 1); NMR (d ₆ -DMSO): δ 10.40 (1H, brs), 10.20 (1H,
s), 8.41 (1H, t, J = 5.4Hz), 7.76 (2H, d, J = 8.0Hz),
7.25 (2H, d, J = 8.0Hz), 3.23 (2H, dt, J = 5.4Hz, J =
7.0Hz), 2.62 (2H, t, J = 8.2Hz), 2.02 (2H, t, J = 7.0H
z), 1.83-1.66 (2H, m), 1.64-1.48 (2H, m), 1.30 (2
H, m), 0.90 (3H, t, J = 7.2Hz).

Example 4 (9) N-hydroxy-4- (N- (benzofuran-2-ylcarbonyl) amino) butyramide

Embedded image TLC: Rf 0.16 (chloroform: methanol: acetic acid = 100: 10: 1); NMR (d ₆ -DMSO): δ 10.38 (1H, brs), 9.30-8.10
(1H, br), 8.75 (1H, t, J = 6.2Hz), 7.76 (1H, m), 7.64
(1H, m), 7.51 (1H, d, J = 0.6Hz), 7.45 (1H, dt, J =
1.6, 7.0Hz), 7.32 (1H, dt, J = 1.0, 7.6Hz), 3.25 (2
H, q, J = 6.2Hz), 2.01 (2H, t, J = 7.0Hz), 1.74 (2H,.
m).

Example 4 (10) N-hydroxy-4- [N- [4- (2- (4-chlorophenyl) ethenyl) phenylcarbonyl] amino] butyramide

Embedded image TLC: Rf 0.17 (chloroform: methanol: acetic acid = 100: 10: 1); NMR (d ₆ -DMSO): δ 10.39 (1H, brs), 8.50 (1H,
t, J = 5.8Hz), 7.86 (2H, d, J = 8.4Hz), 7.67 (2H, d, J
= 8.4Hz), 7.65 (2H, d, J = 8.4Hz), 7.44 (2H, d, J = 8.4H
z), 7.39 (1H, d, J = 16.2Hz), 7.30 (1H, d, J = 16.2H
z), 3.25 (2H, m), 2.02 (2H, t, J = 7.6Hz), 1.74 (2H,
m).

Example 4 (11) N-hydroxy-4- [N- [4-((4- (imidazol-1-yl) phenyl) ethynyl) phenylcarbonyl] amino] butyramide

Embedded image TLC: Rf 0.14 (chloroform: methanol: acetic acid = 100: 10: 1); NMR (d ₆ -DMSO): δ 10.43 (1H, brs), 9.71 (1H,
s), 8.67 (1H, t, J = 5.6Hz), 8.33 (1H, brs), 7.95-7.
82 (8H, m), 7.67 (2H, d, J = 8.4Hz), 3.25 (2H, m),
2.02 (2H, t, J = 7.4Hz), 1.74 (2H, m).

Example 4 (12) N-hydroxy-4- (N- (trans-4-propylcyclohexylcarbonyl) amino) butyramide

Embedded image TLC: Rf 0.34 (chloroform: methanol: acetic acid = 18: 2: 1); NMR (d ₆ -DMSO): δ 10.35 (1H, s), 7.67 (1H, t,
J = 5.3Hz), 2.99 (2H, m), 2.39-1.88 (3H, m), 1.78-1.
61 (6H, m), 1.45-1.07 (7H, m), 0.95-0.76 (5H, m).

Example 4 (13) N-hydroxy-4- [N- [4-((4-methylphenyl) ethynyl) phenylcarbonyl] amino] butyramide

Embedded image TLC: Rf 0.38 (chloroform: methanol: acetic acid = 18: 2: 1); NMR (d ₆ -DMSO): δ 10.39 (1H, s), 8.62-8.53 (1
H, t, J = 5.3Hz), 7.89 (2H, d, J = 8.6Hz), 7.61 (2H, d,
J = 8.6Hz), 7.47 (2H, d, J = 8.0Hz), 7.25 (2H, d, J =
8.0Hz), 3.27 (2H, m), 2.35 (3H, s), 2.03 (2H, t, J
= 6.8Hz), 1.76 (2H, m).

Example 4 (14) N-hydroxy-4- [N- [4-((4-bromophenyl) aminosulfonyl) phenylcarbonyl] amino] butyramide

Embedded image TLC: Rf 0.16 (chloroform: methanol: acetic acid = 18: 2: 1); NMR (d ₆ -DMSO): δ 10.55 (1H, s), 10.38 (1H, b)
rs), 8.67 (1H, m), 7.96 (2H, d, J = 8.4Hz), 7.82 (2
H, d, J = 8.4Hz), 7.43 (2H, d, J = 9.0Hz), 7.06 (2H, d,
J = 9.0Hz), 3.32-3.16 (2H, m), 2.01 (2H, t, J = 7.4H
z), 1.82-1.66 (2H, m).

Example 4 (15) N-hydroxy-4- [N- (4-cyclohexylphenylcarbonyl) amino] butyramide

Embedded image TLC: Rf 0.40 (chloroform: methanol: acetic acid = 18: 2: 1); NMR (d ₆ -DMSO): δ 10.39 (1H, s), 8.43-8.36 (1
H, m), 7.76 (2H, d, J = 8.4Hz), 7.34 (2H, d, J = 8.4H
z), 3.30-3.13 (2H, m), 2.63-2.54 (1H, m), 2.01 (2
H, t, J = 7.6Hz), 1.86-1.65 (6H, m), 1.48-1.24 (6H,
m).

Example 4 (16) N-hydroxy-4- [N- [4- (4-propylphenyl) phenylcarbonyl] amino] butyramide

Embedded image TLC: Rf 0.40 (chloroform: methanol: acetic acid = 18: 2: 1); NMR (d ₆ -DMSO): δ 10.40 (1H, s), 8.70 (1H, br)
s), 8.57-8.49 (1H, m), 7.93 (2H, d, J = 8.5Hz), 7.74
(2H, d, J = 8.5Hz), 7.64 (2H, d, J = 8.5Hz), 7.31 (2H,
d, J = 8.5Hz), 3.31-3.20 (2H, m), 2.61 (2H, t, J = 7.
4Hz), 2.04 (2H, t, J = 7.2Hz), 1.76 (2H, m), 1.62 (2
H, m), 0.92 (3H, t, J = 7.4Hz).

Example 4 (17) N-hydroxy-4- [N- [4- (4-hydroxyphenyl) phenylcarbonyl] amino] butyramide

Embedded image TLC: Rf 0.23 (chloroform: methanol: acetic acid = 18: 2: 1); NMR (d ₆ -DMSO): δ 10.40 (1H, s), 9.80-9.45 (1
H, brs), 8.53-8.44 (1H, m), 7.89 (2H, d, J = 8.5Hz),
7.67 (2H, d, J = 8.5Hz), 7.56 (2H, d, J = 8.8Hz), 6.8
7 (2H, d, J = 8.8Hz), 3.31-3.20 (2H, m), 2.03 (2H,
t, J = 7.4Hz), 1.83-1.68 (2H, m).

Example 4 (18) N-hydroxy-4- [N- [4- (4-chlorophenyl) furan-2-ylcarbonyl] amino] butyramide

Embedded image TLC: Rf 0.38 (chloroform: methanol: acetic acid = 18: 2: 1); NMR (d ₆ -DMSO): δ 10.40 (1H, s), 8.64-8.51 (1
H, m), 7.95 (2H, d, J = 8.4Hz), 7.54 (2H, d, J = 8.4H
z), 7.16-7.11 (2H, m), 3.31-3.18 (2H, m), 2.08-1.9
5 (2H, m), 1.76 (2H, m).

Example 4 (19) N-hydroxy-4- [N- [4- (4-heptylphenyl) phenylcarbonyl] amino] butyramide

Embedded image TLC: Rf 0.34 (chloroform: methanol: acetic acid = 18: 2: 1); NMR (d ₆ -DMSO): δ 10.40 (1H, brs), 8.57-8.50
(1H, m), 7.93 (2H, d, J = 8.4Hz), 7.74 (2H, d, J = 8.4
Hz), 7.64 (2H, d, J = 8.4Hz), 7.30 (2H, d, J = 8.4Hz),
3.32-3.22 (2H, m), 2.62 (2H, t, J = 7.7Hz), 2.04 (2
(H, t, J = 7.3Hz), 1.76 (2H, m), 1.69-1.52 (2H, m),
1.38-1.17 (8H, m), 0.86 (3H, t, J = 6.6Hz).

Example 4 (20) N-hydroxy-4- [N- [4- (4-methoxyphenyl) phenylcarbonyl] amino] butyramide

Embedded image TLC: Rf 0.26 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.40 (1H, s), 8.57-8.47 (1
H, m), 7.91 (2H, d, J = 8.5Hz), 7.71 (2H, d, J = 8.5H
z), 7.68 (2H, d, J = 8.8Hz), 7.05 (2H, d, J = 8.8Hz),
3.81 (3H, s), 3.26 (2H, m), 2.03 (2H, t, J = 7.5Hz),
1.83-1.69 (2H, m).

Example 4 (21) N-hydroxy-4- [N- [4- (4-chlorophenyl) phenylcarbonyl] amino] butyramide

Embedded image TLC: Rf 0.34 (chloroform: methanol: acetic acid = 18: 2: 1); NMR (d ₆ -DMSO): δ 10.41 (1H, s), 8.62-8.52 (1
H, m), 7.95 (2H, d, J = 8.4Hz), 7.82-7.72 (4H, m), 7.
55 (2H, d, J = 8.4Hz), 3.35-3.20 (2H, m), 2.04 (2H,
t, J = 7.5Hz), 1.83-1.69 (2H, m).

Example 4 (22) N-hydroxy-4- [N- (5-benzyloxyindol-2-ylcarbonyl) amino] butyramide

Embedded image TLC: Rf 0.26 (chloroform: methanol: acetic acid: water = 100: 10: 1: 1); NMR (d ₆ -DMSO): δ 11.38 (1H, brs), 10.38 (1H,
brs), 8.70 (1H, brs), 8.43 (1H, t, J = 5.8Hz), 7.28
-7.48 (6H, m), 7.16 (1H, d, J = 2.2Hz), 6.99 (1H, d,
J = 1.4Hz), 6.89 (1H, dd, J = 8.7Hz, 2.4Hz), 5.07 (2H,
s), 3.25 (2H, m), 2.02 (2H, t, J = 6.8Hz), 1.70-1.8
1 (2H, m).

Example 4 (23) N-hydroxy-4- [N- [5- (2- (4-chlorophenyl) ethenyl) furan-2-ylcarbonyl] amino] butyramide

Embedded image TLC: Rf 0.27 (chloroform: methanol: acetic acid: water = 100: 10: 1: 1); NMR (d ₆ -DMSO): δ 10.38 (1H, brs), 8.71 (1H,
brs), 8.46 (1H, t, J = 5.8Hz), 7.60 (2H, d, J = 8.8H
z), 7.43 (2H, d, J = 8.8Hz), 7.23 (1H, d, J = 16.6Hz),
7.15 (1H, d, J = 16.6Hz), 7.09 (1H, d, J = 3.4Hz), 6.
63 (1H, d, J = 3.4Hz), 3.22 (2H, m), 2.00 (2H, t, J =
7.4Hz), 1.73 (2H, m).

Example 4 (24) N-hydroxy-4- [N- (4-phenoxyphenylcarbonyl) amino] butyramide

Embedded image TLC: Rf 0.25 (chloroform: methanol: acetic acid: water = 100: 10: 1: 1); NMR (d ₆ -DMSO): δ 10.36 (1H, brs), 8.69 (1H,
brs), 8.41 (1H, t, J = 5.6Hz), 7.85 (2H, d, J = 8.8H
z), 7.41 (2H, t, J = 7.4Hz), 7.19 (1H, t, J = 7.4Hz),
6.97-7.09 (4H, m), 3.22 (2H, m), 1.99 (2H, t, J = 7.
6Hz), 1.71 (2H, m).

Example 4 (25) N-hydroxy-5- [N- [4- (benzofuran-2
-Yl) phenylcarbonyl] amino] pentanamide

Embedded image TLC: Rf 0.26 (chloroform: methanol = 1
0: 1); NMR (d ₆ -DMSO): δ 10.36 (1H, s), 8.67 (1H, br.
s), 8.57 (1H, t, J = 5.6Hz), 8.01 (2H, d, J = 8.8Hz),
7.96 (2H, d, J = 8.8Hz), 7.71-7.63 (2H, m), 7.57 (1H,
br.s), 7.39-7.23 (2H, m), 3.30-3.23 (2H, m), 2.02
-1.94 (2H, m), 1.60-1.44 (4H, m).

Example 4 (26) N-hydroxy-6- [N- [4- (benzofuran-2)
-Yl) phenylcarbonyl] amino] hexaneamide

Embedded image TLC: Rf 0.28 (chloroform: methanol = 1
0: 1); NMR (d ₆ -DMSO): δ 10.33 (1H, s), 8.80-8.50 (1
H, br.s), 8.54 (1H, t, J = 5.6Hz), 8.01 (2H, d, J = 8.
8Hz), 7.95 (2H, d, J = 8.8H), 7.71-7.62 (2H, m), 7.56
(1H, s), 7.39-7.23 (2H, m), 3.30-3.21 (2H, m), 1.
95 (2H, t, J = 7.2Hz), 1.59-1.46 (4H, m), 1.36-1.20
(2H, m).

Example 4 (27) N-hydroxy-4- [N-[[(4'-carbamoylmethoxy) biphenyl-4-yl] carbonyl] amino] butyramide

Embedded image TLC: Rf 0.22 (chloroform: methanol: acetic acid: water = 50: 10: 1: 1); NMR (d ₆ -DMSO): δ 10.37 (1H, brs), 8.70 (1H, br)
s), 8.49 (1H, t, J = 5.4Hz), 7.89 (2H, d, J = 8.8Hz), 7.
70 (2H, d, J = 8.2Hz), 7.67 (2H, d, J = 8.2Hz), 7.54 (1H,
brs), 7.39 (1H, brs), 7.04 (2H, d, J = 8.8Hz), 4.46 (2
H, s), 3.20-3.31 (2H, m), 2.01 (2H, t, J = 7.2Hz), 1.6
6-1.80 (2H, m).

Example 4 (28) N-hydroxy-4- [N- [4- (4-phenylpiperidin-1-yl) phenylcarbonyl] amino] butyramide

Embedded image TLC: Rf 0.32 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.39 (1H, s), 8.69 (1H, s),
8.20 (1H, t, J = 5.8Hz), 7.73 (2H, d, J = 8.6Hz), 7.4
0-7.12 (5H, m), 6.98 (2H, d, J = 8.6Hz), 4.06-3.90
(2H, m), 3.30-3.16 (2H, m), 2.96-2.60 (3H, m), 2.0
0 (2H, t, J = 7.6Hz), 1.95-1.59 (6H, m).

Example 4 (29) N-hydroxy-4- [N- [4- [3- (4-chlorophenoxy) -1-propynyl] phenylcarbonyl]
Amino] butyramide

Embedded image TLC: Rf 0.26 (chloroform: methanol = 8:
1); NMR (d ₆ -DMSO): δ 10.38 (1H, s), 8.71 (1H, s),
8.57 (1H, t, J = 5.4Hz), 7.85 (2H, d, J = 8.4Hz), 7.5
3 (2H, d, J = 8.4Hz), 7.38 (2H, d, J = 9.2Hz), 7.08 (2
H, d, J = 9.2Hz), 5.08 (2H, s), 3.40-3.15 (2H, m, ov
erlap with H2Oin dmso), 2.02 (2H, t, J = 7.2Hz), 1.7
4 (2H, m).

Example 4 (30) N-hydroxy-4- [N- [4- (3-phenoxy-
1-propynyl) phenylcarbonyl] amino] butyramide

Embedded image TLC: Rf 0.38 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.38 (1H, s), 8.70 (1H, s),
8.57 (1H, t, J = 5.4Hz), 7.85 (2H, d, J = 8.3Hz), 7.5
2 (2H, d, J = 8.3Hz), 7.34 (2H, dd, J = 7.0 and 8.6H
z), 7.10-6.90 (3H, m), 5.06 (2H, s), 3.25 (2H, dt,
J = 5.4 and 7.2Hz), 2.02 (2H, t, J = 7.2Hz), 1.74 (2
H, m).

Example 4 (31) N-hydroxy-4- [N- [4- (4-methoxyphenoxy) phenylcarbonyl] amino] butyramide

Embedded image TLC: Rf 0.40 (chloroform: methanol: acetic acid: water = 50: 10: 1: 1); NMR (d ₆ -DMSO): δ 10.37 (1H, brs), 8.70 (1H, b
rs), 8.40 (1H, t, J = 5.5Hz), 7.82 (2H, d, J = 9.1Hz),
7.06-6.91 (6H, m), 3.79 (3H, s), 3.21 (2H, m), 1.
96 (2H, m), 1.72 (2H, m).

Example 4 (32) N-hydroxy-4- [N- [4- (4-hydroxyphenoxy) phenylcarbonyl] amino] butyramide

Embedded image TLC: Rf 0.25 (chloroform: methanol: acetic acid: water = 50: 10: 1: 1); NMR (d ₆ -DMSO): δ 8.37 (1H, t, J = 5.5 Hz), 7.81
(2H, d, J = 8.8Hz), 6.92 (2H, d, J = 9.1Hz), 6.90 (2H,
d, J = 8.8Hz), 6.80 (2H, d, J = 9.1Hz), 3.21 (2H, m),
1.99 (2H, m), 1.71 (2H, m).

Example 4 (33) N-hydroxy-4- [N- [4- (4-phenoxypiperazin-1-yl) phenylcarbonyl] amino] butyramide

Embedded image TLC: Rf 0.31 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.38 (1H, s), 8.69 (1H, s),
8.19 (1H, t, J = 5.2Hz), 7.73 (2H, d, J = 8.8Hz), 7.2
8 (2H, dd, J = 8.8, 7.4Hz), 7.02-6.87 (5H, m), 4.68-
4.52 (1H, m), 3.73-3.56 (2H, m), 3.32-3.10 (4H,
m), 2.11-1.92 (4H, m), 1.82-1.59 (4H, m).

Example 4 (34) N-hydroxy-4- [N- [4- (4-phenyl-
1,2,5,6-tetrahydropyridin-1-yl) phenylcarbonyl] amino] butyramide

Embedded image TLC: Rf 0.42 (chloroform: methanol: acetic acid: water = 50: 10: 1: 1); NMR (d ₆ -DMSO): δ 10.38 and 9.78 (total 1H, bo
th brs), 9.02 and 8.69 (total 1H, both brs), 8.20
(1H, t, J = 5.5Hz), 7.75 (2H, d, J = 9.1Hz), 7.48 (2H,
m), 7.36 (2H, m), 7.26 (1H, m), 6.98 (2H, d, J = 9.
1Hz), 6.29 (1H, brs), 3.94 (2H, m), 3.58 (2H, m),
3.20 (2H, m), 2.62 (2H, m), 1.99 (2H, m), 1.71 (2
H, m).

Example 4 (35) N-hydroxy-4- [N- [4- (1-heptynyl)
Phenylcarbonyl] amino] butyramide

Embedded image TLC: Rf 0.24 (chloroform: methanol = 1
0: 1); NMR (d ₆ -DMSO): δ 10.37 (1H, s), 8.52 (1H, t,
J = 5.6Hz), 7.80 (2H, d, J = 8.4Hz), 7.44 (2H, d, J = 8.4
Hz), 3.23 (2H, br.q, J = 5.8Hz), 2.43 (2H, t, J = 6.6H
z), 2.00 (2H, t, J = 7.4Hz), 1.79-1.65 (2H, m), 1.62
-1.48 (2H, m), 1.44-1.22 (4H, m), 0.88 (3H, t, J =
6.6Hz).

Example 4 (36) N-hydroxy-4- [N- (4-benzyloxyphenylcarbonyl) amino] butyramide

Embedded image TLC: Rf 0.11 (chloroform: methanol: acetic acid: water = 100: 10: 1: 1); NMR (d ₆ -DMSO): δ 10.36 and 9.78 (total 1H, ea)
ch br), 8.99 and 8.68 (total 1H, each br), 8.31 (1
H, m), 7.80 (2H, d, J = 8.8Hz), 7.45-7.3 (5H, m), 7.
05 (2H, d, J = 8.8Hz), 5.15 (2H, s), 3.21 (2H, m),
1.99 (2H, t, J = 7.4Hz), 1.72 (2H, m).

Example 5 Ethyl 4- (N-methyl-N- (4- (benzofuran-2-yl) phenylcarbonyl) amino) butanoate

Embedded image To a solution of the compound (0.1 g) prepared in Example 1 in dimethylformamide (3 ml) was added methyl iodide (0.35 ml). 60% sodium hydride (13 m
g) was added. The reaction mixture was stirred at room temperature for 1 hour. A 1N aqueous hydrochloric acid solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated to give the title compound (113 mg) having the following physical data. TLC: Rf 0.33 (n-hexane: ethyl acetate = 1:
1).

Example 6 4- (N-methyl-N- (4- (benzofuran-2-yl) phenylcarbonyl) amino) butanoic acid

Embedded image Using the compound prepared in Example 5 in place of the compound prepared in Example 1, and operating in the same manner as in the method shown in Example 2, the title compound having the following physical data was obtained. TLC:
Rf 0.51 (chloroform: methanol = 9: 1); NMR (CD ₃ OD): δ 7.98 (2H, d, J = 8.4 Hz), 7.66-
7.59 (1H, m), 7.57-7.46 (3H, m), 7.37-7.19 (3H,
m), 3.62 and 3.40 (2H, t, J = 7.5Hz), 3.10 and3.03
(3H, s), 2.45 and 2.20 (2H, t, J = 7.5Hz), 2.10-1.75
(2H, m).

Example 7 N-hydroxy-4- (N-methyl-N- (4- (benzofuran-2-yl) phenylcarbonyl) amino) butyramide

Embedded image Using the compound prepared in Example 6 in place of the compound prepared in Example 2, and operating in the same manner as in the method shown in Example 3 → Example 4, the title compound having the following physical data was obtained. TLC: Rf 0.31 (chloroform: methanol = 9:
1); NMR (CD ₃ OD): δ 7.99 (2H, d, J = 8.4 Hz), 7.66-
7.59 (1H, m), 7.58-7.45 (3H, m), 7.37-7.20 (3H,
m), 3.70-3.54 and 3.42-3.30 (2H, m), 3.16-2.95 (3
H, m), 2.30-1.80 (4H, m).

Example 8 Methyl 4- (N- (4- (benzofuran-2-yl) phenylcarbonyl) amino) -2 (S) -hydroxybutanoate

Embedded image Instead of ethyl 4-aminobutanoate, methyl 4-amino-2 (S) -hydroxybutanoate (E
It was produced in the same manner as described in P393441. )) And the title compound having the following physical data was obtained in the same manner as in Example 1. TLC: Rf 0.11 (n-hexane: ethyl acetate = 1:
1); NMR (d ₆ -DMSO): δ 8.58 (1H, t, J = 6.0 Hz), 8.01
(2H, d, J = 8.8Hz), 7.96 (2H, d, J = 8.8Hz), 7.71-7.6
3 (2H, m), 7.57 (1H, brs), 7.39-7.24 (2H, m), 4.19-
4.10 (1H, m), 3.62 (3H, s), 3.38 (2H, q, J = 6.0Hz),
2.06-1.68 (2H, m).

Example 9 4- (N- (4- (benzofuran-2-yl) phenylcarbonyl) amino) -2 (S) -hydroxybutanoic acid

Embedded image Using the compound prepared in Example 8 in place of the compound prepared in Example 1, and operating in the same manner as in the method described in Example 2, the title compound having the following physical data was obtained. TLC: Rf 0.10 (chloroform: methanol: acetic acid = 100: 10: 1); NMR (d ₆ -DMSO): δ 8.49 (1H, t, J = 5.6 Hz), 7.92
(2H, d, J = 8.8Hz), 7.87 (2H, d, J = 8.8Hz), 7.62-7.5
3 (2H, m), 7.48 (1H, d, J = 0.6Hz), 7.30-7.14 (2H,
m), 3.95 (1H, dd, J = 4.4, 8.4Hz), 3.29 (2H, m), 1.9
8-1.58 (2H, m).

Example 9 (1) 4- (N- (4- (benzofuran-2-yl) phenylcarbonyl) amino) -2 (R) -hydroxybutanoic acid

Embedded image Using the same procedure as described in Example 8 → Example 9, except that methyl 4-amino-2 (R) -hydroxybutanoate is used instead of methyl 4-amino-2 (S) -hydroxybutanoate. Thus, the title compound having the following physical data was obtained. TLC: Rf 0.10 (chloroform: methanol: acetic acid = 100: 10: 1); NMR (d ₆ -DMSO): δ 8.49 (1H, t, J = 5.6 Hz), 7.92
(2H, d, J = 8.8Hz), 7.87 (2H, d, J = 8.8Hz), 7.62-7.5
3 (2H, m), 7.48 (1H, d, J = 0.6Hz), 7.30-7.14 (2H,
m), 3.95 (1H, dd, J = 4.4, 8.4Hz), 3.29 (2H, m), 1.9
8-1.58 (2H, m).

Example 10 Methyl 4- (N- (4- (benzofuran-2-yl) phenylcarbonyl) amino) -2 (S) -benzyloxymethoxybutanoate

Embedded image To a solution of the compound prepared in Example 8 (0.2 g) in dichloromethane (1 ml) was added diisopropylethylamine (2 m
l) was added. Benzyloxymethyl chloride (0.79 ml) was added to the mixture. The reaction mixture was stirred at 50 C for 30 minutes. A 1N aqueous hydrochloric acid solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with water and a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by silica gel column chromatography (n-hexane: ethyl acetate = 3: 2) to give the title compound (0.176 g) having the following physical data. TLC: Rf 0.47 (n-hexane: ethyl acetate = 1:
1).

Example 11 4- (N- (4- (benzofuran-2-yl) phenylcarbonyl) amino) -2 (S) -benzyloxymethoxybutanoic acid

Embedded image Using the compound prepared in Example 10 in place of the compound prepared in Example 1, and operating in the same manner as in the method shown in Example 2, the title compound having the following physical data was obtained. TLC: Rf 0.45 (chloroform: methanol: acetic acid = 100: 20: 1); NMR (d ₆ -DMSO): δ 8.61 (1H, t, J = 5.4 Hz), 8.01
(2H, d, J = 8.8Hz), 7.95 (2H, d, J = 8.8Hz), 7.709-7.
63 (2H, m), 7.57 (1H, brs), 4.80 (1H, d, J = 8.8Hz),
4.79 (1H, d, J = 8.8Hz), 4.64 (1H, d, J = 11.8Hz), 4.
54 (1H, d, J = 11.8Hz), 4.13 (1H, dd, J = 4.2, 8.2Hz),
3.52-3.28 (2H, m), 2.12-1.82 (2H, m).

Examples 11 (1) to 11 (3) Using the corresponding amine compounds and acid halides, Example 8
→ Example 10 → The same procedure as in Example 11 was carried out to obtain the compounds shown below.

Example 11 (1) 4- (N- (4- (benzofuran-2-yl) phenylcarbonyl) amino) -2 (R) -benzyloxymethoxybutanoic acid

Embedded image TLC: Rf 0.45 (chloroform: methanol: acetic acid = 100: 20: 1); NMR (d ₆ -DMSO): δ 8.61 (1H, t, J = 5.4 Hz), 8.01
(2H, d, J = 8.8Hz), 7.95 (2H, d, J = 8.8Hz), 7.709-7.
63 (2H, m), 7.57 (1H, brs), 4.80 (1H, d, J = 8.8Hz),
4.79 (1H, d, J = 8.8Hz), 4.64 (1H, d, J = 11.8Hz), 4.
54 (1H, d, J = 11.8Hz), 4.13 (1H, dd, J = 4.2, 8.2Hz),
3.52-3.28 (2H, m), 2.12-1.82 (2H, m).

Example 11 (2) 4- (N- (4- (2- (4-chlorophenyl) ethenyl) phenylcarbonyl) amino) -2 (S) -benzyloxymethoxybutanoic acid

Embedded image TLC: Rf 0.18 (chloroform: methanol = 1
0: 1); NMR (d ₆ -DMSO): δ 8.52 (1H, t, J = 5.4Hz), 7.84
(2H, d, J = 8.4Hz), 7.67 (2H, d, J = 8.4Hz), 7.65 (2
(H, d, J = 8.8Hz), 7.44 (2H, d, J = 8.8Hz), 7.35-7.28
(7H, m), 4.80 (1H, d, J = 8.8Hz), 4.77 (1H, d, J = 8.8Hz)
Hz), 4.63 (1H, d, J = 11.8Hz), 4.54 (1H, d, J = 11.8H)
z), 4.12 (1H, dd, J = 4.4, 8.0Hz), 3.50-3.26 (2H,
m), 2.10-1.78 (2H, m).

Example 11 (3) 4- (N- (4-chlorophenylcarbonyl) amino)
-2-benzyloxymethoxybutanoic acid

Embedded image TLC: Rf 0.32 (chloroform: methanol: acetic acid = 100: 10: 1); NMR (d ₆ -DMSO): δ 8.57 (1H, t, J = 5.6 Hz), 7.84
(2H, d, J = 8.8Hz), 7.52 (2H, d, J = 8.8Hz), 7.30 (5
H, s), 4.80 (1H, d, J = 8.8Hz), 4.76 (1H, d, J = 8.8H
z), 4.63 (1H, d, J = 11.8Hz), 4.53 (1H, d, J = 11.8H)
z), 4.11 (1H, dd, J = 4.4, 8.2Hz), 3.49-3.24 (2H, m),
2.08-1.77 (2H, m).

Example 12 N-hydroxy-4- (N- (4- (benzofuran-2)
-Yl) phenylcarbonyl) amino) -2 (S) -hydroxybutyramide

Embedded image Using the compound produced in Example 9 in place of the compound produced in Example 2, the same procedure as in Example 3 → Example 4 was carried out to obtain the title compound having the following physical properties. TLC: Rf 0.42 (chloroform: methanol: water =
100: 20: 1); NMR (d ₆ -DMSO): δ 10.49
(1H, brs), 8.55 (1H, t, J = 5.4Hz), 8.01 (2H, d, J =
9.0Hz), 7.96 (2H, d, J = 9.0Hz), 7.71-7.62 (2H, m),
7.57 (1H, brs), 7.39-7.23 (2H, m), 3.94 (1H, dd, J
= 4.2, 8.2Hz), 3.41-3.31 (2H, m), 2.02-1.64 (2H,
m).

Examples 12 (1) to 12 (5) Instead of the compound prepared in Example 9, Example 9 (1)
Using the compounds prepared in Example 11 and Examples 11 (1) to 11 (3), the same procedure as in Example 12 was carried out to obtain the compounds shown below.

Example 12 (1) N-hydroxy-4- (N- (4- (benzofuran-2)
-Yl) phenylcarbonyl) amino) -2 (R) -hydroxybutyramide

Embedded image TLC: Rf 0.42 (chloroform: methanol: water =
100: 20: 1); NMR (d ₆ -DMSO): δ 10.49 (1H, brs), 8.55 (1H,
t, J = 5.4Hz), 8.01 (2H, d, J = 9.0Hz), 7.96 (2H, d, J
= 9.0Hz), 7.71-7.63 (2H, m), 7.57 (1H, brs), 7.39-
7.23 (2H, m), 3.94 (1H, dd, J = 4.2, 8.2Hz), 3.41-3.
31 (2H, m), 2.02-1.62 (2H, m).

Example 12 (2) N-hydroxy-4- (N- (4- (benzofuran-2)
-Yl) phenylcarbonyl) amino) -2 (S) -benzyloxymethoxybutyramide

Embedded image TLC: Rf 0.24 (chloroform: methanol = 1
0: 1); NMR (d ₆ -DMSO): δ 10.75 (1H, brs), 8.90 (1H,
brs), 8.55 (1H, t, J = 5.6Hz), 8.01 (2H, d, J = 8.8H
z), 7.96 (2H, d, J = 8.8Hz), 7.71-7.63 (2H, m), 7.58
(1H, brs), 7.39-7.24 (7H, m), 4.77 (1H, d, J = 8.8H
z), 4.68 (1H, d, J = 8.8Hz), 4.58 (2H, s), 4.04 (1H,
t, J = 5.8Hz), 3.49-3.25 (2H, m), 1.93 (2H, m).

Example 12 (3) N-hydroxy-4- (N- (4- (benzofuran-2)
-Yl) phenylcarbonyl) amino) -2 (R) -benzyloxymethoxybutyramide

Embedded image TLC: Rf 0.24 (chloroform: methanol = 1
0: 1); NMR (d ₆ -DMSO): δ 10.75 (1H, brs), 8.90 (1H,
brs), 8.55 (1H, t, J = 5.6Hz), 8.01 (2H, d, J = 8.8H
z), 7.96 (2H, d, J = 8.8Hz), 7.71-7.63 (2H, m), 7.58
(1H, brs), 7.39-7.24 (7H, m), 4.77 (1H, d, J = 8.8H
z), 4.68 (1H, d, J = 8.8Hz), 4.58 (2H, s), 4.04 (1H,
t, J = 5.8Hz), 3.49-3.25 (2H, m), 1.93 (2H, m).

Example 12 (4) N-hydroxy-4- (N- (4- (2- (4-chlorophenyl) ethenyl) phenylcarbonyl) amino)-
2 (S) -benzyloxymethoxybutyramide

Embedded image TLC: Rf 0.22 (chloroform: methanol = 1
0: 1); NMR (d ₆ -DMSO): δ 10.74 (1H, brs), 8.89 (1H,
brs), 8.45 (1H, t, J = 5.6Hz), 7.85 (2H, d, J = 8.4H
z), 7.67 (2H, d, J = 8.4Hz), 7.65 (2H, d, J = 8.6Hz),
7.45 (2H, d, J = 8.6Hz), 7.35-7.26 (7H, m), 4.76 (1
H, d, J = 8.8Hz), 4.67 (1H, d, J = 8.8Hz), 4.57 (2H,
s), 4.02 (1H, t, J = 5.8Hz), 3.48-3.28 (2H, m), 1.91
(2H, m).

Example 12 (5) N-hydroxy-4- (N- (4-chlorophenylcarbonyl) amino) -2-benzyloxymethoxybutyramide

Embedded image TLC: Rf 0.34 (chloroform: methanol = 1
0: 1); NMR (d ₆ -DMSO): δ 10.73 (1H, brs), 8.89 (1H,
brs), 8.52 (1H, m), 7.84 (2H, d, J = 8.4Hz), 7.52 (2
H, d, J = 8.4Hz), 7.30 (5H, brs), 4.75 (1H, d, J = 8.8H
z), 4.66 (1H, d, J = 8.8Hz), 4.56 (2H, s), 4.01 (1H,
t, J = 6.6Hz), 3.45-3.25 (2H, m), 1.89 (2H, m).

Example 13 4- (N- (4-chlorophenylcarbonyl) amino)
-2- (t-butyloxycarbonylmethoxy) butanoic acid methyl ester

Embedded image A solution of methyl 4- (N- (4-chlorophenylcarbonyl) amino) -2-hydroxybutanoate (3 g) in tetrahydrofuran (15 ml) was added to a mixture of 60% sodium hydride (2.38 g) in tetrahydrofuran (10 ml) at -78 ° C. Was added dropwise. The reaction mixture is kept at 0 ° C. for 30 minutes.
After stirring for minutes, t-butyl bromoacetate (0.975
g) was added dropwise at -78 ° C. The reaction mixture was stirred at 0 ° C. for 1.5 hours. A 1N aqueous hydrochloric acid solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium hydrogencarbonate and a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate and concentrated. The residue was subjected to silica gel column chromatography (n-hexane: ethyl acetate = 1: 1).
Purification according to 1) gave the title compound (3.194 g) having the following physical data. TLC: Rf 0.63 (n-hexane: ethyl acetate = 1:
1).

Example 14 4- (N- (4-chlorophenylcarbonyl) amino)
-2- (Carboxymethoxy) butanoic acid methyl ester

Embedded image A solution of the compound prepared in Example 13 (3.194 g) in trifluoroacetic acid (50 ml) was stirred at room temperature for 1 hour. The reaction mixture was concentrated and crystallized by adding diethyl ether,
The residue was washed with diethyl ether and dried to give the title compound (2.275 g) having the following physical data. TLC: Rf 0.28 (chloroform: methanol: acetic acid = 100: 10: 1).

Example 15 4- (N- (4-chlorophenylcarbonyl) amino)
-2-((N-benzyl-N-methylamino) carbonylmethoxy) butanoic acid methyl ester

Embedded image N-Benzyl-N-methylamine (0.213 g), 1-hydroxybenzotriazole hydrate (0.27 g), 1-ethyl-N-benzyl-N-methylamine (0.213 g) were added to a solution of the compound (0.5 g) prepared in Example 14 in dimethylformamide (5 ml). 3- (3-dimethylaminopropyl) carbodiimide hydrochloride (0.337 g)
Was added under ice cooling, and the mixture was stirred at room temperature for 1 hour. 1 in the reaction mixture
An N hydrochloric acid aqueous solution was added, and the mixture was extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium hydrogen carbonate and a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, and concentrated.
The title compound (0.664 g) having the following physical data was obtained. TLC: Rf 0.60 (n-hexane: ethyl acetate = 1:
1).

Example 16 4- (N- (4-chlorophenylcarbonyl) amino)
-2-((N-benzyl-N-methylamino) carbonylmethoxy) butanoic acid

Embedded image Using the compound prepared in Example 15 in place of the compound prepared in Example 1, and operating in the same manner as in the method shown in Example 2, the title compound having the following physical data was obtained. TLC: Rf 0.21 (chloroform: methanol: acetic acid = 100: 10: 1); NMR (d ₆ -DMSO): δ 8.83 and 8.72 (total 1H,
m), 7.87 and 7.86 (total 2H, d, J = 8.8Hz), 7.53-7.2
3 (7H, m), 4.53 and 4.49 (total 2H, s), 4.38 (1H,
d, J = 15.0Hz), 4.24 (1H, d, J = 15.0Hz), 3.52-3.37 (1
H, m), 2.86 and 2.80 (total 3H, s), 2.08-1.72 (2H,
m).

Examples 16 (1) and 16 (2) Using the corresponding amine compound in place of N-benzyl-N-methylamine, the same procedure as in Example 15 → Example 16 was carried out. The following compounds were obtained.

Example 16 (1) 4- (N- (4-chlorophenylcarbonyl) amino)
-2-((N-phenyl-N-methylamino) carbonylmethoxy) butanoic acid

Embedded image TLC: Rf 0.29 (chloroform: methanol: acetic acid = 100: 10: 1); NMR (d ₆ -DMSO): δ 8.72 (1H, t, J = 5.8 Hz), 7.88
(2H, d, J = 8.4Hz), 7.53 (2H, d, J = 8.4Hz), 7.49-7.3
4 (5H, m), 4.05-3.82 (3H, m), 3.44-3.33 (2H, m),
3.19 (3H, s), 2.04-1.64 (2H, m).

Example 16 (2) 4- (N- (4-chlorophenylcarbonyl) amino)
-2-((N-phenylethyl-N-methylamino) carbonylmethoxy) butanoic acid

Embedded image TLC: Rf 0.32 (chloroform: methanol: acetic acid = 100: 10: 1); NMR (d ₆ -DMSO): δ 8.83 (0.5H, t, J = 5.5 Hz), 8.
75 (0.5H, t, J = 5.5Hz), 7.89 (1H, d, J = 8.4Hz), 7.86
(1H, d, J = 8.4Hz), 7.53 (1H, d, J = 8.4Hz), 7.49 (1H,
d, J = 8.4Hz), 7.30 (5H, s), 4.39 (0.5H, d, J = 15.4H
z), 4.17 (0.5H, d, J = 15.4Hz), 4.13 (0.5H, d, J = 14.
6Hz), 3.95 (0.5H, dd, J = 8.8, 3.0Hz), 3.90 (0.5H,
d, J = 14.6Hz), 3.79 (0.5H, dd, J = 9.0, 3.6Hz), 3.60-
3.30 (4H, m), 2.90-2.70 (2H, m), 2.10-1.60 (2H,
m).

Example 17 N-hydroxy-4- (N- (4-chlorophenylcarbonyl) amino) -2-((N-benzyl-N-methylamino) carbonylmethoxy) butyramide

Embedded image Using the compound prepared in Example 16 in place of the compound prepared in Example 2, the same procedure as in Example 3 → Example 4 was carried out to obtain the title compound having the following physical properties. TLC: Rf 0.39 (chloroform: methanol = 1
0: 1); NMR (d ₆ -DMSO): δ 10.93 and 10.90 (total 1H,
brs, and brs), 9.05-8.65 (2H, m), 7.87 and 7.86 (t
otal 2H, d and d, J = 8.8Hz and J = 8.8Hz), 7.52 and
7.45 (total 2H, d and d, J = 8.8Hz and J = 8.8Hz), 7.3
7-7.19 (5H, m), 4.54 and 4.50 (total 2H, s and s),
4.44 and 4.36 (total 1H, d and d, J = 14.2Hz and J = 1
5.0Hz), 4.24 and 4.20 (total 1H, d and d, J = 14.2Hz
and J = 15.0Hz), 3.94-3.88 (1H, m), 2.84 and 2.80
(total 3H, s and s), 2.00-1.68 (2H, m).

Examples 17 (1) and 17 (2) Instead of the compound prepared in Example 16, Example 16
Using the compounds prepared in (1) and 16 (2), the same procedure as in Example 17 was carried out to obtain the following compounds.

Example 17 (1) N-hydroxy-4- (N- (4-chlorophenylcarbonyl) amino) -2-((N-phenyl-N-methylamino) carbonylmethoxy) butyramide

Embedded image TLC: Rf 0.48 (chloroform: methanol = 1
0: 1); NMR (d ₆ -DMSO): δ 10.79 (1H, brs), 9.20-8.40
(1H, br), 8.68 (1H, m), 7.87 (2H, d, J = 8.8Hz), 7.53
(2H, d, J = 8.8Hz), 7.46-7.34 (5H, m), 4.14-3.67 (3
H, m), 3.55-3.25 (2H, m), 3.19 (3H, s), 1.95-1.60
(2H, m).

Example 17 (2) N-hydroxy-4- (N- (4-chlorophenylcarbonyl) amino) -2-((N-phenylethyl-N-
Methylamino) carbonylmethoxy) butyramide

Embedded image TLC: Rf 0.40 (chloroform: methanol = 1
0: 1); NMR (d ₆ -DMSO): δ 10.90 (1H, brs), 8.87 (1H,
brs), 8.83-8.67 (1H, m), 7.89 and 7.87 (total 2H, d
and d, J = 8.4Hz and J = 8.4Hz), 7.53 and 7.49 (total
2H, d and d, J = 8.4Hz and J = 8.4Hz), 7.33-7.17 (5H,
m), 4.31 and 4.10 and 3.99 (total 2H, d and d and
s, J = 15.4Hz and J = 15.4Hz), 3.85 and 3.69 (total 1
H, dd and dd, J = 4.4, 8.8Hz and J = 4.0, 8.4Hz), 3.56
-3.32 (2H, m), 2.84-2.72 (2H, m), 1.97-1.68 (2H, m
m).

Example 18 Methyl 3 (S) -hydroxy-4- (N- (4- (benzofuran-2-yl) phenylcarbonyl) amino) butanoate

Embedded image 3 (S) instead of 4-aminobutanoic acid ethyl ester
-Hydroxy-4-aminobutanoic acid methyl ester (Ac
The same procedure as in Example 1 was carried out using ta Chem. Scand., Ser. B, 37 , 341 (1983)) to give the title compound having the following physical data. TLC: Rf 0.31 (n-hexane: ethyl acetate = 1:
1); NMR (d ₆ -DMSO): δ 8.57 (1H, t, J = 6.0 Hz), 8.00
(4H, s), 7.71-7.63 (2H, m), 7.57 (1H, brs), 7.40-
7.24 (2H, m), 5.13 (1H, d, J = 5.6Hz), 4.18-4.00 (1
H, m), 3.57 (3H, s), 3.30 (2H, t, J = 6.0Hz), 2.55
(1H, dd, J = 4.0,15.0Hz), 2.31 (1H, dd, J = 4.0, 15.0H
z).

Example 19 3 (S) -Hydroxy-4- (N- (4- (benzofuran-2-yl) phenylcarbonyl) amino) butanoic acid

Embedded image The title compound having the following physical data was obtained in the same manner as in Example 2, except that the compound prepared in Example 18 was used instead of the compound prepared in Example 1. TLC: Rf 0.24 (chloroform: methanol: acetic acid = 100: 10: 1); NMR (d ₆ -DMSO): δ 8.55 (1H, t, J = 5.8 Hz), 8.00
(4H, s), 7.71-7.63 (2H, m), 7.58 (1H, brs), 7.39-
7.23 (2H, m), 5.16-4.92 (1H, brs), 4.14-4.00 (1H,
m), 3.30 (2H, t, J = 5.8Hz), 2.46 (1H, dd, J = 4.2, 1
5.0Hz), 2.23 (1H, dd, J = 8.4, 15.0Hz).

Example 19 (1) 3 (R) -hydroxy-4- (N- (4- (benzofuran-2-yl) phenylcarbonyl) amino) butanoic acid

Embedded image The procedure of Example 18 → Example 19 was repeated, using 3 (R) -hydroxy-4-aminobutanoic acid ethyl ester instead of 3 (S) -hydroxy-4-aminobutanoic acid methyl ester, to obtain the following. The title compound having the following physical data was obtained. TLC: Rf 0.24 (chloroform: methanol: acetic acid = 100: 10: 1); NMR (d ₆ -DMSO): δ 8.55 (1H, t, J = 5.8 Hz), 8.00
(4H, s), 7.71-7.63 (2H, m), 7.58 (1H, brs), 7.39-
7.23 (2H, m), 5.16-4.92 (1H, brs), 4.14-4.00 (1H,
m), 3.30 (2H, t, J = 5.8Hz), 2.46 (1H, dd, J = 4.2, 1
5.0Hz), 2.23 (1H, dd, J = 8.4, 15.0Hz).

Example 20 3 (S) -methoxymethyloxy-4- (N- (4-
(Benzofuran-2-yl) phenylcarbonyl) amino) butanoic acid and 4- (N- (4- (benzofuran-
2-yl) phenylcarbonyl) amino) -2-butenoic acid

Embedded image

Embedded image Example 10 (Using methoxymethyl chloride in place of benzyloxymethyl chloride) using the compound prepared in Example 18 → The title compound having the following physical data was operated in the same manner as shown in Example 11. Was obtained respectively.

Example 20 (1) TLC: Rf 0.21 (chloroform: methanol = 1
0: 1); NMR (d ₆ -DMSO): δ 8.72 (1H, t, J = 5.6 Hz), 8.00
(4H, s), 7.72-7.64 (2H, m), 7.60 (1H, brs), 7.40-
7.20 (2H, m), 4.63 (2H, s), 4.08 (1H, m), 3.40 (2H,
m), 2.40-2.20 (2H, m).

Example 20 (2) TLC: Rf 0.12 (chloroform: methanol = 1)
0: 1); NMR (d ₆ -DMSO): δ 8.88 (1H, t, J = 5.6 Hz), 8.02
(4H, s), 7.71-7.62 (2H, m), 7.59 (1H, brs), 7.40-
7.20 (2H, m), 6.80 (1H, dt, J = 15.0, 5.0Hz), 5.85
(1H, d, J = 15.0Hz), 4.09-4.01 (2H, m).

Example 20 (3) 3 (R) -methoxymethyloxy-4- (N- (4-
(Benzofuran-2-yl) phenylcarbonyl) amino) butanoic acid

Embedded image The procedure of Example 18 → Example 20 was repeated, using 3 (R) -hydroxy-4-aminobutanoic acid ethyl ester instead of 3 (S) -hydroxy-4-aminobutanoic acid methyl ester. The title compound having the following physical data was obtained. TLC: Rf 0.21 (chloroform: methanol = 1
0: 1); NMR (d ₆ -DMSO): δ 8.72 (1H, t, J = 5.6 Hz), 8.01
(4H, s), 7.70-7.65 (2H, m), 7.61 (1H, brs), 7.40-
7.20 (2H, m), 4.62 (2H, s), 4.08 (1H, m), 3.42 (2H,
m), 2.40-2.20 (2H, m).

Example 21 3 (S) -Acetyloxy-4- (N- (4- (benzofuran-2-yl) phenylcarbonyl) amino) butanoic acid methyl ester

Embedded image The compound (0.3 g) prepared in Example 18 was treated with pyridine (5
Acetic anhydride (0.6 ml) was added to the solution at 0 ° C. The reaction mixture was stirred at room temperature for 2 hours. A 1N aqueous hydrochloric acid solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. Extract with water,
The extract was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate and concentrated to give the title compound (0.325 g) having the following physical data. TLC: Rf 0.52 (n-hexane: ethyl acetate = 1:
2).

Example 22 Methyl 4- (N- (4- (benzofuran-2-yl) phenylcarbonyl) amino) -3-butenoic acid

Embedded image 1,8-diazabicyclo [5.
4.0] Undec-7-ene [DBU] (0.13 ml) was added. The reaction mixture was stirred at 50 C for 3 hours. A 1N aqueous hydrochloric acid solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate.
The extract was washed with water and a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate and concentrated to give the title compound (0.096 g) having the following physical data. TLC: Rf 0.70 (n-hexane: ethyl acetate = 1:
2).

Example 23 4- (N- (4- (benzofuran-2-yl) phenylcarbonyl) amino) -3-butenoic acid

Embedded image The title compound having the following physical data was obtained in the same manner as in the method described in Example 2, except that the compound prepared in Example 22 was used instead of the compound prepared in Example 1. TLC: Rf 0.22 (chloroform: methanol: acetic acid = 100: 10: 1); NMR (d ₆ -DMSO): δ 10.39 (1H, d, J = 9.8 Hz), 8.0
5 (4H, s), 7.72-7.64 (2H, m), 7.61 (1H, d, J = 0.6H
z), 7.41-7.24 (2H, m), 6.95 (1H, dd, J = 9.8,14.4H
z), 5.54 (1H, dt, J = 14.4, 7.2Hz), 3.05 (2H, d, J =
7.2Hz).

Example 24 N-hydroxy-3 (S) -hydroxy-4- (N-
(4- (benzofuran-2-yl) phenylcarbonyl) amino) butyramide

Embedded image Using the compound prepared in Example 19 instead of the compound prepared in Example 2, the same procedure as in Example 3 → Example 4 was carried out to obtain the title compound having the following physical properties. TLC: Rf 0.41 (chloroform: methanol: water =
100: 20: 1); NMR (d ₆ -DMSO): δ 10.39 (1H, brs), 8.55 (1H,
m), 8.00 (4H, s), 7.71-7.63 (2H, m), 7.57 (1H, br
s), 7.39-7.23 (2H, m), 5.50-4.30 (1H, br), 4.12-3.9
8 (1H, m), 3.40-3.18 (2H, m), 2.16 (1H, dd, J = 4.8,
14.0Hz), 2.03 (1H, dd, J = 8.2, 14.0Hz).

Examples 24 (1) to 24 (6) Example 19 was repeated in place of the compound prepared in Example 19.
(1) Using the compounds prepared in Examples 20 (1) to 20 (3) and Example 23, operating in the same manner as in the method shown in Example 24, or using the compounds prepared in Example 18 The title compound having the following physical data was obtained in the same manner as in Example 10, Example 11, and Example 24.

Example 24 (1) N-hydroxy-3 (R) -hydroxy-4- (N-
(4- (benzofuran-2-yl) phenylcarbonyl) amino) butyramide

Embedded image TLC: Rf 0.41 (chloroform: methanol: water =
100: 20: 1); NMR (d ₆ -DMSO): δ 10.39 (1H, brs), 8.55 (1H,
m), 8.00 (4H, s), 7.71-7.63 (2H, m), 7.58 (1H, br
s), 7.39-7.24 (2H, m), 5.20-3.80 (1H, br), 4.12-3.9
8 (1H, m), 3.40-3.18 (2H, m), 2.16 (1H, dd, J = 4.8,
14.0Hz), 2.03 (1H, dd, J = 8.2, 14.0Hz).

Example 24 (2) N-hydroxy-3 (S) -methoxymethyloxy-4
-(N- (4- (benzofuran-2-yl) phenylcarbonyl) amino) butyramide

Embedded image TLC: Rf 0.19 (chloroform: methanol = 1
0: 1); NMR (d ₆ -DMSO): δ 10.47 (1H, brs), 8.80 (1H,
brs), 8.64 (1H, t, J = 5.8Hz), 8.02 (2H, d, J = 9.2H
z), 7.97 (2H, d, J = 9.2Hz), 7.71-7.63 (2H, m), 7.57
(1H, brs), 7.40-7.24 (2H, m), 4.60 (2H, s), 4.16-
4.04 (1H, m), 3.41 (2H, t, J = 5.8Hz), 3.21 (3H, s),
2.22-2.18 (2H, m).

Example 24 (3) N-hydroxy-4- (N- (4- (benzofuran-2)
-Yl) phenylcarbonyl) amino) -2-butenamide

Embedded image TLC: Rf 0.20 (chloroform: methanol: acetic acid = 100: 10: 1); NMR (d ₆ -DMSO): δ 10.60 (1H, brs), 8.89 (1H,
t, J = 5.8Hz), 8.02 (4H, s), 7.71-7.63 (2H, m), 7.59
(1H, brs), 7.40 (2H, m), 6.69 (1H, dt, J = 15.4, 4.
8Hz), 5.86 (1H, d, J = 15.4Hz), 4.08-4.02 (2H, m).

Example 24 (4) N-hydroxy-3 (R) -methoxymethyloxy-4
-(N- (4- (benzofuran-2-yl) phenylcarbonyl) amino) butyramide

Embedded image TLC: Rf 0.19 (chloroform: methanol = 1
0: 1); NMR (d ₆ -DMSO): δ 10.46 (1H, brs), 8.77 (1H,
brs), 8.64 (1H, t, J = 5.8Hz), 8.02 (2H, d, J = 9.2H
z), 7.97 (2H, d, J = 9.2Hz), 7.71-7.63 (2H, m), 7.58
(1H, brs), 7.40-7.24 (2H, m), 4.60 (2H, s), 4.16-
4.05 (1H, m), 3.42 (2H, t, J = 5.8Hz), 3.22 (3H, s),
2.22-2.19 (2H, m).

Example 24 (5) N-hydroxy-4- (N- (4- (benzofuran-2)
-Yl) phenylcarbonyl) amino) -3-butenamide

Embedded image TLC: Rf 0.21 (chloroform: methanol: acetic acid = 100: 10: 1); NMR (d ₆ -DMSO): δ 10.45 (1H, brs), 10.37 (1H,
d, J = 9.6Hz), 8.98-8.52 (1H, brs), 8.04 (4H, s),
7.72-7.63 (2H, m), 7.61 (1H, brs), 7.41-7.24 (2H,
m), 6.94 (1H, dd, J = 9.6, 14.2Hz), 5.53 (1H, dt, J =
14.2, 7.8Hz), 2.76 (2H, d, J = 7.8Hz).

Example 24 (6) N-hydroxy-4- [N- [4- (benzofuran-2)
-Yl) phenylcarbonyl] amino] -3 (S) -benzyloxymethoxybutyramide

Embedded image TLC: Rf 0.31 (chloroform: methanol = 1
0: 1); NMR (d ₆ -DMSO): δ 10.51 (1H, s), 8.67 (1H, t,
J = 5.6Hz), 7.98 (4H, m), 7.71-7.60 (2H, m), 7.57 (1
H, br.s), 7.39-7.20 (7H, m), 4.77 (1H, d, J = 6.8Hz),
4.73 (1H, d, J = 6.8Hz), 4.51 (2H, s), 4.20 (1H,
m), 3.49-3.43 (2H, m), 2.25 (2H, d, J = 6.2Hz).

Example 25 2-benzyloxymethyl-4- (N- (4-methylphenylcarbonyl) amino) butanoic acid

Embedded image Diisopropylamine (0.925 ml) in tetrahydrofuran (5 ml) and hexamethylphosphoramide (HMP
A) (3 ml) solution at -78 ° C under argon atmosphere for 1.
63 M hexane solution of n-butyllithium (4.05 ml)
Was added. The mixture was stirred at -78 C for 15 minutes. To this solution was added a solution of the compound prepared in Example 2 (1) (0.442 g) in tetrahydrofuran (3 ml) at -78 ° C. The reaction mixture was stirred at room temperature for 30 minutes. The reaction mixture was added at −78 ° C. with benzyloxymethyl chloride (0.31
3g) was added. The reaction mixture was stirred at -78 C for 2 hours. A 1N aqueous hydrochloric acid solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated to give the title compound (0.22 g) having the following physical data. TLC: Rf 0.67 (chloroform: methanol: acetic acid = 18: 2: 1).

Example 26 N-hydroxy-2-benzyloxymethyl-4- (N
-(4-methylphenylcarbonyl) amino) butyramide

Embedded image The title compound having the following physical properties was obtained by operating in the same manner as in the method shown in Example 3 → Example 4 using the compound produced in Example 25 instead of the compound produced in Example 2. TLC: Rf 0.36 (chloroform: methanol = 1
0: 1); NMR (d ₆ -DMSO): δ 10.52 (1H, s), 8.86 (1H,
s), 8.32 (1H, t, J = 8.4Hz), 7.74 (2H, d, J = 8.4Hz),
7.31 (5H, m), 7.24 (2H, d, J = 8.4Hz), 4.46 (1H, d,
J = 12.5Hz), 4.44 (1H, d, J = 12.5Hz), 3.59 (1H, dd, J
= 8.8, 8.8Hz), 3.41 (1H, dd, J = 8.8, 5.5Hz), 3.21 (2
H, m), 2.44 (1H, m), 2.35 (3H, s), 1.66 (2H, m).

Example 27 N-hydroxy-2-hydroxymethyl-4- (N-
(4-methylphenylcarbonyl) amino) butyramide

Embedded image To a solution of the compound prepared in Example 26 (0.24 g) in methanol (10 ml) was added 10% palladium-carbon (0.024 g) under an argon atmosphere. The reaction mixture was stirred at room temperature under a hydrogen atmosphere for 2 hours. The reaction mixture was filtered through Celite (trade name), and the filtrate was concentrated. The residue was purified by silica gel column chromatography (chloroform: methanol = 10: 1) to give the title compound (0.158 g) having the following physical data. TLC: Rf 0.39 (ethyl acetate: acetic acid: water = 16:
3: 2); NMR (d ₆ -DMSO): δ 8.41 (1H, m), 7.76 (2H, d,
J = 8.0Hz), 7.24 (2H, d, J = 8.0Hz), 3.52 (1H, m), 3.37
(1H, m), 3.20 (2H, m), 2.35 (3H, s), 2.23 (1H,
m), 1.64 (2H, m).

Examples 27 (1) and 27 (2) The same procedure as described in Example 3 → Example 4 → Example 27 was carried out using the compound prepared in Example 25 by separation by liquid chromatography. Then, the following compound was obtained.

Example 27 (1) N-hydroxy-2-hydroxymethyl-4- (N-
(4-methylphenylcarbonyl) amino) butyramide

Embedded image (In the formula, * represents the R or S form. The steric structure has not yet been determined. However, it represents the opposite steric form of Example 27 (2).) TLC: Rf 0.17 (chloroform : Methanol = 4:
1); NMR (CD ₃ OD): δ 7.70 (2H, d, J = 8.2 Hz), 7.26
(2H, d, J = 8.2Hz), 3.79-3.52 (2H, m), 3.50-3.25 (2
H, m), 2.38 (3H, s), 2.38-2.25 (1H, m), 1.80 (2H, q
-like).

Example 27 (2) N-hydroxy-2-hydroxymethyl-4- (N-
(4-methylphenylcarbonyl) amino) butyramide

Embedded image (Wherein * represents the R or S form. The steric structure has not yet been determined. However, it represents the opposite steric form of Example 27 (1).) TLC: Rf 0.17 (chloroform : Methanol = 4:
1); NMR (CD ₃ OD): δ 7.70 (2H, d, J = 8.2 Hz), 7.26
(2H, d, J = 8.2Hz), 3.79-3.52 (2H, m), 3.50-3.25 (2
H, m), 2.38 (3H, s), 2.38-2.25 (1H, m), 1.80 (2H, q
-like).

Reference Example 5 t-butyl 4- (S) -methylaminocarbonyl-4- (N-benzyloxycarbonylamino) butanoate

Embedded image The title compound having the following physical data was prepared in the same manner as in Example 15, using 4 (S) -carboxy-4- (N-benzyloxycarbonylamino) butanoic acid t-butyl ester and methylamine. I got TLC: Rf 0.73 (chloroform: methanol = 9:
1); NMR (CDCl ₃ ): δ 7.38-7.31 (5H, m), 6.24 (1H,
m), 5.65 (1H, m), 5.10 (2H, s), 4.20-4.12 (1H, m),
2.81 (3H, d, J = 5.0Hz), 2.49-2.24 (2H, m), 2.17-1.8
5 (2H, m), 1.44 (9H, s).

Reference Example 6 4 (S) -methylaminocarbonyl-4-aminobutanoic acid t-butyl ester

Embedded image The title compound having the following physical data was obtained in the same manner as in Example 27, using the compound prepared in Reference Example 5 instead of the compound prepared in Example 26. TLC: Rf 0.28 (chloroform: methanol = 9:
1).

Example 28 4 (S) -Methylaminocarbonyl-4- (N- (4-
Methylphenylcarbonyl) amino) butanoic acid t-butyl ester

Embedded image The title compound having the following physical data was obtained in the same manner as in Example 1, except that the compound prepared in Reference Example 6 was used instead of the compound prepared in Reference Example 4. TLC: Rf 0.46 (chloroform: methanol = 9:
1).

Example 294 4 (S) -Methylaminocarbonyl-4- (N- (4-
Methylphenylcarbonyl) amino) butanoic acid

Embedded image The title compound having the following physical properties was obtained by operating in the same manner as in the method shown in Example 14, using the compound produced in Example 28 instead of the compound produced in Example 13. TLC: Rf 0.40 (chloroform: methanol = 9:
1). NMR (d ₆ -DMSO): δ 12.13 (1H, brs), 8.33 (1H,
d, J = 7.8Hz), 7.86-7.78 (3H, m), 7.26 (2H, d, J = 8.1
Hz), 4.40-4.25 (1H, m), 2.59 (3H, d, J = 4.8Hz), 2.3
6 (3H, s), 2.30-2.23 (2H, m), 2.05-1.82 (2H, m).

Examples 29 (1) to 29 (3) The same procedures as in Example 5 → Reference Example 6 → Example 28 → Example 29 were carried out using the corresponding amine compound in place of the methylamine compound. Then, the following compound was obtained.

Example 29 (1) 4 (R) -methylaminocarbonyl-4- (N- (4-
Methylphenylcarbonyl) amino) butanoic acid

Embedded image TLC: Rf 0.20 (chloroform: methanol = 5:
1); NMR (CDCl ₃ + CD ₃ OD): δ 7.60-7.33 (2H, m), 7.1
4-7.22 (2H, m), 4.52-4.66 (1H, m), 2.76 (3H, s),
2.30-2.56 (2H, m), 2.34 (3H, s), 1.84-2.22 (2H,
m).

Example 29 (2) 4 (S) -benzylaminocarbonyl-4- (N- (4
-Methylphenylcarbonyl) amino) butanoic acid

Embedded image TLC: Rf 0.51 (chloroform: methanol = 4:
1); NMR (d ₆ -DMSO): δ 12.10 (1H, brs), 8.44 (2H,
d, J = 8.0Hz), 7.82 (2H, d, J = 8.0Hz), 7.27-7.21 (5H,
m), 4.49-4.40 (1H, m), 3.60 (1H, brs), 3.17 (2H,
s), 2.36 (3H, s), 2.40-2.25 (2H, m), 2.20-1.95 (2
H, m).

Example 29 (3) 4 (S)-(4-hydroxybutyl) aminocarbonyl-4- (N- (4-methylphenylcarbonyl) amino) butanoic acid

Embedded image TLC: Rf 0.33 (chloroform: methanol = 4:
1).

Example 30 N-hydroxy-4 (S) -methylaminocarbonyl-
4- (N- (4-methylphenylcarbonyl) amino)
Butyramide

Embedded image The title compound having the following physical properties was obtained by operating in the same manner as in the method shown in Example 3 → Example 4 using the compound produced in Example 29 instead of the compound produced in Example 2. TLC: Rf 0.69 (chloroform: methanol = 4:
1); NMR (d ₆ -DMSO): δ 10.37 (1H, brs), 8.69 (1H,
m), 8.43 (1H, d, J = 7.6Hz), 7.85-7.79 (3H, m), 7.25
(2H, d, J = 8.0Hz), 4.40-4.25 (1H, m), 2.59 (3H, d,
J = 4.6Hz), 2.06 (3H, s), 2.10-1.85 (4H, m).

Examples 30 (1) to 30 (3) Instead of the compound prepared in Example 29, Example 29 was used.
Example 3 Using Compounds Produced in (1) to 29 (3)
By operating in the same manner as in the method shown by 0, the following compounds were obtained.

Example 30 (1) N-hydroxy-4 (R) -methylaminocarbonyl-
4- (N- (4-methylphenylcarbonyl) amino)
Butyramide

Embedded image TLC: Rf 0.30 (chloroform: methanol = 1
0: 1); NMR (CD ₃ OD): δ 7.72 (2H, d, J = 8 Hz), 7.20 (2
(H, d, J = 8Hz), 4.44-4.50 (1H, m), 2.67 (3H, s), 2.3
1 (3H, s), 2.22-1.85 (4H, m).

Example 30 (2) N-hydroxy-4 (S) -benzylaminocarbonyl-4- (N- (4-methylphenylcarbonyl) amino) butyramide

Embedded image TLC: Rf 0.42 (chloroform: methanol = 4:
1).

Example 30 (3) N-hydroxy-4 (S)-(4-hydroxybutyl)
Aminocarbonyl-4- (N- (4-methylphenylcarbonyl) amino) butyramide

Embedded image TLC: Rf 0.23 (chloroform: methanol: acetic acid = 18: 2: 1); NMR (CDCl ₃ ): δ 7.74 (2H, d, J = 7.5 Hz), 7.39
(1H, s), 7.25 (2H, d, J = 7.5Hz), 4.60-4.43 (1H, m),
3.61-3.56 (2H, m), 3.31-3.15 (2H, m), 2.40 (3H, s),
2.30-2.04 (4H, m), 1.62-1.48 (4H, m).

Example 31 4 (S) -Methoxycarbonyl-4- [N- [4- (4
-(Tetrahydropyran-2-yloxy) -1-butynyl) phenylcarbonyl] amino] butanoic acid t-butyl ester

Embedded image 4 (S) -methoxycarbonyl-4-aminobutanoic acid t
The title compound having the following physical data was obtained in the same manner as in Example 1 using -butyl ester and the corresponding acid halide. TLC: Rf 0.35 (n-hexane: ethyl acetate = 1:
2); NMR (CDCl ₃ ): δ 7.78 (2H, d, J = 8.4 Hz), 7.44
(2H, d, J = 8.4Hz), 7.21 (3H, s), 3.70-3.50 (2H, m),
2.75 (2H, t, J = 6.9Hz), 2.42 (2H, m), 2.30-2.00 (2
H, m), 2.00-1.50 (6H, m), 1.42 (9H, s).

Example 32 4 (S) -Methoxycarbonyl-4- [N- [4- (4
-Hydroxy-1-butynyl) phenylcarbonyl] amino] butanoic acid

Embedded image The title compound having the following physical data was obtained in the same manner as in the method shown in Example 14, except that the compound produced in Example 13 was used instead of the compound produced in Example 13. TLC: Rf 0.11 (n-hexane: ethyl acetate = 1:
1); NMR (CDCl ₃ + CD ₃ OD): δ 8.02 (1H, d, J = 7.6 Hz),
7.77 (2H, d, J = 8.6Hz), 7.44 (2H, d, J = 8.6Hz), 4.8
2-4.70 (1H, m), 3.83-3.69 (5H, m), 2.68 (2H, t, J =
6.6Hz), 2.41 (2H, t, J = 6.6Hz), 2.26-1.99 (2H, m).

Example 33 N-hydroxy-4 (S) -methoxycarbonyl-4-
[N- [4- (4-hydroxy-1-butynyl) phenylcarbonyl] amino] butyramide

Embedded image Using the compound prepared in Example 32 in place of the compound prepared in Example 2, and operating in the same manner as in the method shown in Example 3 → Example 4, the title compound having the following physical data was obtained. TLC: Rf 0.30 (chloroform: methanol: acetic acid = 18: 2: 1); NMR (d ₆ -DMSO): δ 10.44 (1H, s), 10.20 (1H,
s), 8.89 (1H, d, J = 6.6Hz), 7.87 (2H, d, J = 7.8Hz),
7.47 (2H, d, J = 7.8Hz), 4.41 (1H, m), 3.66 (3H, s),
3.65-3.59 (2H, m), 2.58 (2H, t, J = 6.6Hz), 2.18-1.
95 (2H, m), 1.28-1.21 (2H, m).

Example 33 (1) N-hydroxy-4 (R) -carbonyl-4- [N-
[4- (3-Methoxy-1-propynyl) phenylcarbonyl] amino] butyramide

Embedded image Using the method shown in Example 31 → Example 2 → Example 33 → Example 14 using 4 (R) -t-butoxycarbonyl-4-aminobutanoic acid methyl ester and the corresponding acid halide, The title compound having the following physical data was obtained. TLC: Rf 0.18 (chloroform: methanol: acetic acid: water = 85: 15: 1: 1); NMR (d ₆ -DMSO): δ 7.86 (2H, d, J = 8.8 Hz), 7.53 (2
H, d, J = 8.8Hz), 4.54-4.59 (1H, m), 4.34 (2H, s), 3.4
3 (3H, s), 2.05-2.36 (4H, m).

Example 34 4 (S) -tert-Butoxycarbonyl-4- (N- (4-
Methylphenylcarbonyl) amino) butanoic acid benzyl ester

Embedded image The title compound having the following physical properties was obtained by operating in the same manner as in Example 1 using benzyl 4 (S) -t-butoxycarbonyl-4-aminobutanoate and the corresponding acid halide. TLC: Rf 0.19 (n-hexane: ethyl acetate = 4:
1).

Example 35 4 (S) -t-butoxycarbonyl-4- (N- (4-
Methylphenylcarbonyl) amino) butanoic acid

Embedded image The title compound having the following physical data was obtained in the same manner as in Example 27, using the compound prepared in Example 34 instead of the compound prepared in Example 26. TLC: Rf 0.38 (chloroform: methanol = 5:
1); NMR (CDCl ₃ ): δ 7.70 (2H, d, J = 8.2 Hz), 7.22
(2H, d, J = 8.2Hz), 6.97 (1H, d, J = 7.5Hz), 4.71 (1H,
m), 2.47 (2H, m), 2.38 (3H, s), 2.28 (1H, m), 2.05
(1H, m), 1.49 (9H, s).

Example 36 N-hydroxy-4 (S) -carboxy-4- (N-
(4-methylphenylcarbonyl) amino) butyramide

Embedded image Using the compound prepared in Example 35 in place of the compound prepared in Example 2, the same procedure as in Example 3 → Example 14 was carried out to obtain the title compound having the following physical data. TLC: Rf 0.43 (ethyl acetate: acetic acid: water = 8: 1:
1); NMR (CD ₃ OD): δ 7.78 (2H, d, J = 8.0 Hz), 7.28
(2H, d, J = 8.0Hz), 4.56 (1H, m), 2.40 (3H, s), 2.00
-2.38 (4H, m).

Example 37 Methyl 4 (S) -carboxy-4- (N- (4- (benzofuran-2-yl) phenylcarbonyl) amino) butanoic acid

Embedded image Using 4 (S) -carboxy-4-aminobutanoic acid methyl ester and the compound produced in Reference Example 4, the same procedure as in Example 1 was carried out to give the title compound having the following physical data. TLC: Rf 0.64 (chloroform: methanol: acetic acid = 18: 2: 1); NMR (CD ₃ OD): δ 12.74 (1H, brs), 8.74 (1H, d,
J = 7.8Hz), 8.04 (4H, s), 7.71-7.58 (3H, m), 7.42-7.
26 (2H, m), 4.45 (1H, m), 3.60 (3H, s), 2.51-2.44
(2H, m), 2.26-1.96 (2H, m).

Example 38 4 (S)-(morpholin-1-yl) carbonyl-4-
(N- (4- (benzofuran-2-yl) phenylcarbonyl) amino) butanoic acid

Embedded image By using the compound prepared in Example 37 in place of the compound prepared in Example 14, and operating in the same manner as in the method shown in Example 15 → Example 16, the title compound having the following physical data was obtained. TLC: Rf 0.48 (chloroform: methanol = 4:
1); NMR (d ₆ -DMSO): δ 12.23 (1H, brs), 8.72 (1H,
d, J = 8.0Hz), 8.05-8.01 (4H, m), 7.74-7.58 (3H, m),
7.42-7.24 (2H, m), 5.03-4.86 (1H, m), 3.63-3.45
(8H, m), 2.37 (2H, t, J = 7.0Hz), 2.04-1.84 (2H,
m).

Example 39 Methyl 4 (S) -hydroxymethyl-4- (N- (4- (benzofuran-2-yl) phenylcarbonyl) amino) butanoate

Embedded image N-hydroxysuccinimide (2.2 g) and dichlorohexylcarbodiimide (4.0 g) were added to a solution of the compound (5.7 g) prepared in Example 37 in tetrahydrofuran (30 ml) at 0 ° C.
1 g) was added. The reaction mixture was stirred at 0 C for 5 hours.
The reaction mixture was filtered, and sodium borohydride (1.19 g) and water (5 ml) were added to the filtrate at 0 ° C. The reaction mixture was stirred at room temperature for 30 minutes. A saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated to give the title compound (4.89 g) having the following physical data. TLC: Rf 0.21 (n-hexane: ethyl acetate = 3:
7); NMR (d ₆ -DMSO): δ 8.14 (1H, d, J = 8.4 Hz), 7.99
(4H, s), 7.72-7.60 (2H, m), 7.55 (1H, d, J = 0.8Hz),
7.40-7.24 (2H, m), 4.75 (1H, t, J = 5.8Hz), 4.10-3.
90 (1H, m), 3.56 (3H, s), 3.55-3.39 (2H, m), 2.36
(2H, t, J = 7.4Hz), 2.06-1.62 (2H, m).

Example 40 4 (S) -Hydroxymethyl-4- (N- (4- (benzofuran-2-yl) phenylcarbonyl) amino) butanoic acid

Embedded image The title compound having the following physical data was obtained in the same manner as in Example 2, except that the compound prepared in Example 39 was used instead of the compound prepared in Example 1. TLC: Rf 0.33 (chloroform: methanol: acetic acid = 190: 10: 1); NMR (d ₆ -DMSO): δ 12.10-11.90 (1H, br), 8.14
(1H, d, J = 8.8Hz), 8.00 (4H, s), 7.73-7.60 (2H, m),
7.55 (1H, s), 7.41-7.22 (2H, m), 4.80-4.64 (1H,
m), 4.10-3.90 (1H, m), 3.54-3.35 (2H, m), 2.28 (2
H, t, J = 6.8Hz), 2.02-1.60 (2H, m).

Example 41 4 (S) -methoxymethyloxymethyl-4- (N-
(4- (benzofuran-2-yl) phenylcarbonyl) amino) butanoic acid methyl ester

Embedded image Using the compound prepared in Example 39 in place of the compound prepared in Example 8, operating in the same manner as in Example 10 (using methoxymethyl chloride instead of benzyloxymethyl chloride), The title compound having physical properties was obtained. TLC: Rf 0.65 (n-hexane: ethyl acetate = 3:
7); NMR (CDCl ₃ ): δ 7.94 (2H, d, J = 8.8 Hz), 7.87
(2H, d, J = 8.8Hz) 7.64-7.50 (2H, m), 7.38-7.21 (2H,
m), 7.13 (1H, d, J = 0.8Hz), 6.78 (1H, d, J = 7.8Hz),
4.67 (2H, s), 4.46-4.28 (1H, m), 3.78 (1H, dd, J = 1
0.2, 3.4Hz), 3.65 (1H, dd, J = 10.2, 4.4Hz), 3.64 (3
H, s), 3.39 (3H, s), 2.62-2.38 (2H, m), 2.16-2.00
(2H, m).

Example 42 4 (S) -Methoxymethyloxymethyl-4- (N-
(4- (benzofuran-2-yl) phenylcarbonyl) amino) butanoic acid

Embedded image The title compound having the following physical data was obtained in the same manner as in Example 2, except that the compound prepared in Example 41 was used instead of the compound prepared in Example 1. TLC: Rf 0.19 (chloroform: methanol = 1
9: 1); NMR (d ₆ -DMSO): δ 12.02 (1H, s), 8.30 (1H, d,
J = 8.2Hz), 8.00 (4H, s), 7.73-7.60 (2H, m), 7.56 (1
H, s), 7.41-7.22 (2H, m), 4.58 (2H, s), 4.26-4.08
(1H, m), 3.62-3.42 (2H, m), 3.32 (3H, s), 3.26 (3
H, s), 2.29 (2H, t, J = 6.8Hz), 2.02-1.62 (2H, m).

Example 43 2 (S) -Benzyl-4 (S) -methoxymethyloxymethyl-4- (N- (4- (benzofuran-2-yl)
Phenylcarbonyl) amino) butanoic acid methyl ester

Embedded image To a solution of 1.0 M lithium bis (trimethylsilyl) amide in tetrahydrofuran (0.695 ml) in tetrahydrofuran (5 ml) was added at −78 ° C. a solution of the compound prepared in Example 41 (0.474 g) in tetrahydrofuran (5 ml). After the mixture was stirred at -78 C for 1 hour, benzyl bromide (0.113 ml) was added. The reaction mixture was -78
Stirred at C for 3 hours. A saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography (n-hexane: ethyl acetate = 3: 2) to give the title compound (0.429 g) having the following physical data.
I got TLC: Rf 0.51 (n-hexane: ethyl acetate = 1:
1); NMR (CDCl ₃ ): δ 7.96 (2H, d, J = 8.8 Hz), 7.84
(2H, d, J = 8.8Hz), 7.63-7.50 (2H, m), 7.38-7.10 (8
H, m), 6.57 (1H, d, J = 8.8Hz), 4.64 (1H, d, J = 8.8H
z), 4.60 (1H, d, J = 8.8Hz), 4.50-4.30 (1H, m), 3.70
(1H, dd, J = 10.2, 3.2Hz), 3.59 (1H, dd, J = 10.2, 3.8
Hz), 3.40 (3H, s), 3.35 (3H, s), 3.04-2.72 (3H,
m), 2.19 (1H, ddd, J = 14.2, 10.4, 8.4Hz), 1.82 (1H,
dt, J = 14.2, 4.4Hz).

Example 44 2 (S) -benzyl-4 (S) -methoxymethyloxymethyl-4- (N- (4- (benzofuran-2-yl)
Phenylcarbonyl) amino) butanoic acid

Embedded image The title compound having the following physical data was obtained in the same manner as in Example 2, except that the compound prepared in Example 43 was used instead of the compound prepared in Example 1. TLC: Rf 0.31 (chloroform: methanol = 1
9: 1); NMR (CDCl ₃ ): δ 7.85 (2H, d, J = 8.8 Hz), 7.79
(2H, d, J = 8.8Hz), 7.58-7.45 (2H, m), 7.36-7.10 (7
H, m), 7.04 (1H, d, J = 0.8Hz), 6.73 (1H, d, J = 8.8H
z), 4.60 (1H, d, J = 8.8Hz), 4.56 (1H, d, J = 8.8Hz),
4.50-4.30 (1H, m), 3.70 (1H, dd, J = 10.6, 3.2Hz),
3.57 (1H, dd, J = 10.6, 3.8Hz), 3.29 (3H, s), 3.11-2.
95 (1H, m), 2.90-2.75 (2H, m), 2.24-2.01 (1H, m),
1.90-1.72 (1H, m).

Examples 44 (1) to 44 (27) Example 37 → Example 39 → Example 41 (corresponding to methoxymethyl chloride using the corresponding compound instead of the compound prepared in Reference Example 4 ) A compound may be used in some cases.) → Example 43 (using a corresponding compound in place of benzyl bromide) → In the same manner as in the method shown in Example 44, the following compound was obtained.

Example 44 (1) 2 (S) -methyl-4 (S) -methoxymethyloxymethyl-4- (N- (4- (benzofuran-2-yl) phenylcarbonyl) amino) butanoic acid

Embedded image TLC: Rf 0.25 (chloroform: methanol = 1
9: 1); NMR (CDCl ₃ ): δ 7.89 (2H, d, J = 8.8 Hz), 7.83
(2H, d, J = 8.8Hz), 7.62-7.50 (2H, m), 7.37-7.20 (2
H, m), 7.09 (1H, d, J = 1.0Hz), 6.63 (1H, d, J = 8.8H
z), 4.65 (2H, s), 4.55-4.36 (1H, m), 3.75 (1H, dd,
J = 10.2, 3.2Hz), 3.62 (1H, dd, J = 10.2, 4.0Hz), 3.38
(3H, s), 2.70-2.50 (1H, m), 2.23 (1H, ddd, J = 14.0,
11.0, 8.2Hz), 1.72 (1H, ddd, J = 14.0, 6.0, 4.4Hz),
1.30 (3H, d, J = 6.8Hz).

Example 44 (2) 2 (S)-(3-phenyl-2-propenyl) -4
(S) -methoxymethyloxymethyl-4- (N- (4
-(Benzofuran-2-yl) phenylcarbonyl) amino) butanoic acid

Embedded image TLC: Rf 0.44 (n-hexane: ethyl acetate = 3:
7); NMR (d ₆ -DMSO): δ 12.23 (1H, s), 8.34 (1H, d,
J = 8.4Hz), 8.00 (4H, s), 7.74-7.61 (2H, m), 7.57 (1
H, s), 7.41-7.18 (7H, m), 6.43 (1H, d, J = 15.6Hz),
6.20 (1H, dt, J = 15.6, 6.4Hz), 4.57 (2H, s), 4.40-
4.20 (1H, m), 3.62-3.48 (2H, m), 3.23 (3H, s), 2.60
-2.40 (3H, m), 1.92-1.80 (2H, m).

Example 44 (3) 2 (S)-(3-phenylpropyl) -4 (S) -methoxymethyloxymethyl-4- (N- (4- (benzofuran-2-yl) phenylcarbonyl) amino ) Butanoic acid

Embedded image TLC: Rf 0.44 (n-hexane: ethyl acetate = 3:
7); NMR (CDCl ₃ ): δ 7.85 (2H, d, J = 8.8 Hz), 7.79
(2H, d, J = 8.8Hz), 7.60-7.44 (2H, m), 7.34-7.06 (7
H, m), 7.03 (1H, d, J = 0.8Hz), 6.69 (1H, d, J = 8.8H
z), 4.62 (1H, d, J = 8.8Hz), 4.60 (1H, d, J = 8.8Hz),
4.48-4.28 (1H, m), 3.73 (1H, dd, J = 10.2, 3.4Hz),
3.59 (1H, dd, J = 10.2, 4.0Hz), 3.34 (3H, s), 2.68-2.
42 (3H, m), 2.21-2.00 (1H, m), 1.86-1.52 (5H, m).

Example 44 (4) 2 (S) -Methyl-5-ethoxymethoxy-4 (S)-
[N- (4-chlorophenylcarbonyl) amino] pentanoic acid

Embedded image TLC: Rf 0.46 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 12.06 (1H, s), 8.24 (1H, d,
J = 8.7Hz), 7.83 (2H, d, J = 8.4Hz), 7.51 (2H, d,
J = 8.4Hz), 4.57 (2H, s), 4.24-4.13 (1H, m), 3.52-
3.42 (4H, m), 2.37-2.25 (1H, m), 1.92-1.80 (1H,
m), 1.63-1.52 (1H, m), 1.06 (3H, t, J = 6.9Hz), 1.
05 (3H, d, J = 6.9Hz).

Example 44 (5) 2 (S) -Methyl-5-ethoxymethoxy-4 (S)-
[N- (4-nitrophenylcarbonyl) amino] pentanoic acid

Embedded image TLC: Rf 0.45 (methylene chloride: methanol = 9:
1); NMR (CDCl ₃ ): δ 8.27 (d, J = 9.0 Hz, 2H), 7.96
(d, J = 9.0Hz, 2H), 6.89 (brd, J = 9.0Hz, 1H), 4.73
(d, J = 7.0Hz, 1H), 4.68 (d, J = 7.0Hz, 1H), 4.40
(m, 1H), 3.78 (dd, J = 10.6, 3.2Hz, 1H), 3.68-3.55
(m, 3H), 2.55 (m, 1H), 2.16 (ddd, J = 14.4, 10.2,
7.6Hz, 1H), 1.70 (ddd, J = 14.4,5.8, 5.0Hz, 1H),
1.28 (d, J = 7.0 Hz, 3H), 1.20 (t, J = 7.0 Hz, 3H).

Example 44 (6) 2 (S) -methyl-5-ethoxymethoxy-4 (S)-
[N- (4-bromophenylcarbonyl) amino] pentanoic acid

Embedded image TLC: Rf 0.47 (methylene chloride: methanol = 9:
1); NMR (CDCl ₃ ): δ 7.65 (d, J = 8.8 Hz, 2H), 7.54
(d, J = 8.8Hz, 2H), 6.67 (brd, J = 9.2Hz, 1H), 4.72
(d, J = 7.0Hz, 1H), 4.67 (d, J = 7.0Hz, 1H), 4.40
(m, 1H), 3.75 (dd, J = 10.4, 3.2Hz, 1H), 3.66-3.55
(m, 3H), 2.55 (m, 1H), 2.16 (ddd, J = 14.4, 10.2,
7.6Hz, 1H), 1.70 (ddd, J = 14.4,6.6, 4.8Hz, 1H),
1.27 (d, J = 7.0Hz, 3H), 1.20 (t, J = 7.0Hz, 3H).

Example 44 (7) 2 (S) -allyl-5-ethoxymethoxy-4 (S)-
[N- (4-nitrophenylcarbonyl) amino] pentanoic acid

Embedded image TLC: Rf 0.31 (chloroform: methanol = 9:
1); NMR (CDCl ₃ ): δ 8.25 (d, J = 8.7 Hz, 2H), 7.94
(d, J = 8.7Hz, 2H), 6.92 (d, J = 8.7Hz, 1H), 5.82-
5.68 (m, 1H), 5.14-5.06 (m, 2H), 4.73 (d, J = 6.9H
z, 1H), 4.68 (d, J = 6.9Hz, 1H), 4.45-4.32 (m, 1
H), 3.79 (dd, J = 10.2, 3.3Hz, 1H), 3.66-3.56 (m, 3
H), 2.63-2.31 (m, 3H), 2.14-2.03 (m, 1H), 1.82 (dt,
J = 14.1, 5.4Hz, 1H), 1.20 (t, J = 7.2Hz, 3H).

Example 44 (8) 2 (R) -methoxymethyl-5-ethoxymethoxy-4
(S)-[N- (4-nitrophenylcarbonyl) amino] pentanoic acid

Embedded image TLC: Rf 0.24 (chloroform: methanol = 1
9: 1); NMR (CDCl ₃ ): δ 8.25 (d, J = 8.7 Hz, 2H), 7.95
(d, J = 8.7Hz, 2H), 7.11 (d, J = 8.4Hz, 1H), 4.73
(d, J = 5.7Hz, 1H), 4.67 (d, J = 5.7Hz, 1H), 4.42-
4.31 (m, 1H), 3.80 (dd, J = 10.2, 3.3Hz, 1H), 3.69
-3.57 (m, 5H), 3.39 (s, 3H), 2.82-2.70 (m, 1H), 2.1
7 (ddd, J = 14.4, 10.2, 8.1Hz, 1H), 1.88 (dt, J = 1
4.4, 5.1Hz, 1H), 1.20 (t, J = 7.2Hz, 3H).

Example 44 (9) 2 (R) -benzyloxymethyl-5-ethoxymethoxy-4 (S)-[N- (4-nitrophenylcarbonyl) amino] pentanoic acid

Embedded image TLC: Rf 0.41 (chloroform: methanol = 1
9: 1); NMR (CDCl ₃ ): δ 8.24 (d, J = 8.8 Hz, 2H), 7.93
(d, J = 8.8Hz, 2H), 7.41-7.20 (m, 5H), 7.01 (d, J =
8.8Hz, 1H), 4.72 (d, J = 7.4Hz, 1H), 4.67 (d, J =
7.4Hz, 1H), 4.57 (s, 2H), 4.43-4.25 (m, 1H), 3.82
-3.52 (m, 6H), 2.89-2.70 (m, 1H), 2.19 (ddd, J = 1
4.8, 10.2, 8.0Hz, 1H), 1.70 (dt, J = 14.8, 5.0Hz, 1
H), 1.19 (t, J = 7.0 Hz, 3H).

Example 44 (10) 2 (S) -Methyl-5- (2-methoxyethoxy) methoxy-4 (S)-[N- (4-cyanophenylcarbonyl) amino] pentanoic acid

Embedded image TLC: Rf 0.40 (chloroform: methanol = 1
9: 1); NMR (CDCl ₃ ): δ 7.91 (d, J = 8.4 Hz, 2H), 7.70
(d, J = 8.4Hz, 2H), 7.07 (d, J = 9.0Hz, 1H), 4.75
(d, J = 6.9Hz, 1H), 4.70 (d, J = 6.9Hz, 1H), 4.45-
4.34 (m, 1H), 3.84 (dd, J = 10.5, 3.3Hz, 1H), 3.78
-3.60 (m, 3H), 3.54-3.51 (m, 2H), 3.29 (s, 3H), 2.61
-2.49 (m, 1H), 2.15 (ddd, J = 14.1,10.2, 7.5Hz, 1
H), 1.70 (ddd, J = 14.1,6.6, 5.1Hz, 1H), 1.20 (d,
J = 6.9Hz, 3H).

Example 44 (11) 2 (R)-(2-methoxyethoxy) methyl-5-ethoxymethoxy-4 (S)-[N- (4-nitrophenylcarbonyl) amino] pentanoic acid

Embedded image TLC: Rf 0.17 (chloroform: methanol = 1
9: 1); NMR (CDCl ₃ ): δ 8.26 (d, J = 8.8 Hz, 2H), 7.97
(d, J = 8.8Hz, 2H), 7.08 (d, J = 8.8Hz, 1H), 4.75-
4.62 (m, 2H), 4.44-4.28 (m, 1H), 3.82-3.48 (m, 10
H), 3.37 (s, 3H), 2.90-2.66 (m, 1H), 2.21 (ddd, J
= 14.4, 10.0, 8.6Hz, 1H), 1.92 (dt, J = 14.4, 4.8H
z, 1H), 1.20 (t, J = 7.0Hz, 3H).

Example 44 (12) 2 (S)-(2-propynyl) -5-ethoxymethoxy-4 (S)-[N- (4-nitrophenylcarbonyl)
Amino] pentanoic acid

Embedded image TLC: Rf 0.30 (chloroform: methanol = 9:
1); NMR (CDCl ₃ ): δ 8.28 (d, J = 9.0 Hz, 2H), 7.96
(d, J = 9.0Hz, 2H), 6.98 (d, J = 8.7Hz, 1H), 4.75
(d, J = 6.9Hz, 1H), 4.70 (d, J = 6.9Hz, 1H), 4.50-
4.38 (m, 1H), 3.84 (dd, J = 10.5, 3.0Hz, 1H), 3.70
-3.55 (m, 3H), 2.80-2.40 (m, 3H), 2.28-2.10 (m, 1
H), 2.10-1.95 (m, 2H), 1.21 (t, J = 7.2Hz, 3H).

Example 44 (13) 2 (S) -allyl-5- (2-methoxyethoxy) methoxy-4 (S)-[N- (4-cyanophenylcarbonyl) amino] pentanoic acid

Embedded image TLC: Rf 0.26 (chloroform: methanol = 1
9: 1); NMR (CDCl ₃ ): δ 7.90 (d, J = 8.4 Hz, 2H), 7.71
(d, J = 8.4Hz, 2H), 7.10 (d, J = 9.0Hz, 1H), 5.82-
5.66 (m, 1H), 5.16-5.03 (m, 2H), 4.75 (d, J = 6.9H
z, 1H), 4.70 (d, J = 6.9Hz, 1H), 4.38 (m, 1H), 3.8
5 (dd, J = 10.5, 3.6Hz, 1H), 3.80-3.58 (m, 3H), 3.
54 (t, J = 4.5Hz, 2H), 3.31 (s, 3H), 2.62-2.50 (m,
1H), 2.49-2.30 (m, 2H), 2.07 (dt, J = 14.4, 9.0Hz,
1H), 1.83 (dt, J = 14.4, 5.4Hz, 1H).

Example 44 (14) 2 (S) -methoxymethyl-5- (2-methoxyethoxy) methoxy-4 (S)-[N- (4-cyanophenylcarbonyl) amino] pentanoic acid

Embedded image TLC: Rf 0.35 (chloroform: methanol = 9:
1); NMR (CD ₃ OD): δ 7.94 (d, J = 8.7 Hz, 2H), 7.82
(d, J = 8.7Hz, 2H), 4.71 (d, J = 6.6Hz, 1H), 4.68
(d, J = 6.6Hz, 1H), 4.39-4.31 (m, 1H), 3.68-3.49
(m, 8H), 3.32 (s, 3H), 3.31 (s, 3H), 2.76-2.66 (m,
1H), 2.08-1.86 (m, 2H).

Example 44 (15) 2 (S)-(2-propynyl) -5-ethoxymethoxy-4 (S)-[N- (4-bromophenylcarbonyl)
Amino] pentanoic acid

Embedded image TLC: Rf 0.36 (chloroform: methanol = 9:
1); NMR (CDCl ₃ ): δ 7.64 (d, J = 8.6 Hz, 2H), 7.54
(d, J = 8.6Hz, 2H), 6.82 (d, J = 9.0Hz, 1H), 4.72
(d, J = 6.9Hz, 1H), 4.69 (d, J = 6.9Hz, 1H), 4.50-
4.35 (m, 1H), 3.80 (dd, J = 10.4, 3.2Hz, 1H), 3.70
-3.55 (m, 3H), 2.78-2.45 (m, 3H), 2.25-2.10 (m, 1
H), 2.10-1.95 (m, 2H), 1.20 (t, J = 7.2Hz, 3H).

Example 44 (16) 2 (S)-(2-propynyl) -5-ethoxymethoxy-4 (S)-[N- (4-chlorophenylcarbonyl)
Amino] pentanoic acid

Embedded image TLC: Rf 0.36 (chloroform: methanol = 9:
1); NMR (CDCl ₃ ): δ 7.71 (d, J = 8.7 Hz, 2H), 7.38
(d, J = 8.7Hz, 2H), 6.81 (d, J = 8.7Hz, 1H), 4.73
(d, J = 6.8Hz, 1H), 4.69 (d, J = 6.8Hz, 1H), 4.50-
4.35 (m, 1H), 3.80 (dd, J = 10.2, 3.0Hz, 1H), 3.70
-3.55 (m, 3H), 2.78-2.45 (m, 3H), 2.25-2.10 (m, 1
H), 2.10-1.95 (m, 2H), 1.20 (t, J = 7.2Hz, 3H).

Example 44 (17) 2 (R) -methoxymethyl-5-ethoxymethoxy-4
(S)-[N- (4-bromophenylcarbonyl) amino] pentanoic acid

Embedded image TLC: Rf 0.39 (chloroform: methanol = 9:
1); NMR (CD ₃ OD): δ 7.73-7.69 (m, 2H), 7.65-7.59
(m, 2H), 4.67 (s, 2H), 4.37-4.28 (m, 1H), 3.63-3.5
3 (m, 6H), 3.32 (s, 3H), 2.75-2.64 (m, 1H), 1.96-
1.89 (m, 2H), 1.15 (t, J = 7.2Hz, 3H).

Example 44 (18) 2 (R) -methoxymethyl-5-ethoxymethoxy-4
(S)-[N- (4-chlorophenylcarbonyl) amino] pentanoic acid

Embedded image TLC: Rf 0.32 (chloroform: methanol = 9:
1); NMR (CD ₃ OD): δ 7.78 (d, J = 8.7 Hz, 2H), 7.45
(d, J = 8.7Hz, 2H), 4.66 (s, 2H), 4.37-4.27 (m, 1
H), 3.63-3.54 (m, 6H), 3.32 (s, 3H), 2.74-2.62 (m,
1H), 1.97-1.88 (m, 2H), 1.15 (t, J = 7.2Hz, 3H).

Example 44 (19) 2 (R) -benzyloxymethyl-5- (2-methoxyethoxy) methoxy-4 (S)-[N- (4-cyanophenylcarbonyl) amino] pentanoic acid

Embedded image TLC: Rf 0.48 (methylene chloride: methanol = 9:
1); NMR (CDCl ₃ ): δ 7.87 (d, J = 8.4 Hz, 2H), 7.67
(d, J = 8.4Hz, 2H), 7.31 (m, 5H), 7.16 (brd, J = 9.
0Hz, 1H), 4.74 (d, J = 7.2Hz, 1H), 4.69 (d, J = 7.
2Hz, 1H), 4.55 (s, 2H), 4.34 (m, 1H), 3.83 (dd, J
= 10.2, 3.6Hz, 1H), 3.77-3.66 (m, 4H), 3.62 (dd, J
= 10.2, 4.2Hz, 1H), 3.51 (t, J = 4.5Hz, 2H), 3.29
(s, 3H), 2.79 (m, 1H), 2.15 (ddd, J = 14.1, 9.6,
7.5Hz, 1H), 1.91 (ddd, J = 14.1, 5.4, 5.4Hz, 1H).

Example 44 (20) 2 (R) -Benzyloxymethyl-5-ethoxymethoxy-4 (S)-[N- (4-chlorophenylcarbonyl) amino] pentanoic acid

Embedded image TLC: Rf 0.50 (methylene chloride: methanol = 9:
1); NMR (CDCl ₃ ): δ 7.69 (d, J = 8.8 Hz, 2H), 7.35
(d, J = 8.8Hz, 2H), 7.31 (m, 5H), 6.81 (brd, J = 8.
8Hz, 1H), 4.70 (d, J = 7.5Hz, 1H), 4.66 (d, J = 7.
5Hz, 1H), 4.55 (s, 2H), 4.33 (m, 1H), 3.80-3.50
(m, 6H), 2.80 (m, 1H), 2.15 (ddd, J = 14.2, 9.8,
7.6Hz, 1H), 1.89 (ddd, J = 14.2, 5.2,5.2Hz, 1H),
1.17 (t, J = 7.4Hz, 3H).

Example 44 (21) 2 (R) -Benzyloxymethyl-5-ethoxymethoxy-4 (S)-[N- (4-bromophenylcarbonyl) amino] pentanoic acid

Embedded image TLC: Rf 0.50 (methylene chloride: methanol = 9:
1); NMR (CDCl ₃ ): δ 7.62 (d, J = 8.8 Hz, 2H), 7.51
(d, J = 8.8Hz, 2H), 7.31 (m, 5H), 6.81 (brd, J = 8.
8Hz, 1H), 4.70 (d, J = 7.0Hz, 1H), 4.65 (d, J = 7.
0Hz, 1H), 4.54 (s, 2H), 4.33 (m, 1H), 3.80-3.50
(m, 6H), 2.79 (m, 1H), 2.15 (ddd, J = 14.2, 9.8,
7.6Hz, 1H), 1.89 (ddd, J = 14.2, 5.2,5.2Hz, 1H),
1.18 (t, J = 7.4Hz, 3H).

Example 44 (22) 2 (S) -Allyl-5-ethoxymethoxy-4 (S)-
[N- (4-bromophenylcarbonyl) amino] pentanoic acid

Embedded image TLC: Rf 0.43 (chloroform: methanol = 9:
1); NMR (CDCl ₃ ): δ 7.63 (d, J = 8.7 Hz, 2H), 7.53
(d, J = 8.7Hz, 2H), 6.72 (d, J = 9.0Hz, 1H), 5.83-
5.65 (m, 1H), 5.18-5.02 (m, 2H), 4.71 (d, J = 6.8H
z, 1H), 4.67 (d, J = 6.8Hz, 1H), 4.45-4.30 (m, 1
H), 3.76 (dd, J = 10.4, 3.2Hz, 1H), 3.70-3.50 (m, 3
H), 2.62-2.50 (m, 1H), 2.50-2.25 (m, 2H), 2.18-2.00
(m, 1H), 1.81 (td, J = 14.1, 5.1Hz, 1H), 1.20 (t,
J = 7.1Hz, 3H).

Example 44 (23) 2 (S) -allyl-5-ethoxymethoxy-4 (S)-
[N- (4-chlorophenylcarbonyl) amino] pentanoic acid

Embedded image TLC: Rf 0.45 (chloroform: methanol = 9:
1); NMR (CDCl ₃ ): δ 7.70 (d, J = 8.7 Hz, 2H), 7.38
(d, J = 8.7Hz, 2H), 6.73 (d, J = 9.0Hz, 1H), 5.82-
5.65 (m, 1H), 5.18-5.02 (m, 2H), 4.71 (d, J = 6.8H
z, 1H), 4.67 (d, J = 6.8Hz, 1H), 4.45-4.30 (m, 1
H), 3.76 (dd, J = 10.5, 3.3Hz, 1H), 3.70-3.50 (m, 3
H), 2.62-2.50 (m, 1H), 2.50-2.25 (m, 2H), 2.18-2.00
(m, 1H), 1.81 (td, J = 14.1, 5.3Hz, 1H), 1.20 (t,
J = 6.9Hz, 3H).

Example 44 (24) 2 (R)-(2-methoxyethoxy) methyl-5-ethoxymethoxy-4 (S)-[N- (4-bromophenylcarbonyl) amino] pentanoic acid

Embedded image TLC: Rf 0.41 (chloroform: methanol = 9:
1); NMR (CDCl ₃ ): δ 7.65 (d, J = 8.8 Hz, 2H), 7.54
(d, J = 8.8Hz, 2H), 6.85 (d, J = 8.8Hz, 1H), 4.70
(d, J = 7.0Hz, 1H), 4.66 (d, J = 7.0Hz, 1H), 4.42-
4.27 (m, 1H), 3.78-3.50 (m, 10H), 3.35 (s, 3H), 2.
83-2.70 (m, 1H), 2.18 (ddd, J = 14.0, 9.8, 7.0Hz,
1H), 1.82 (ddd, J = 14.0, 5.6, 4.4Hz, 1H), 1.18
(t, J = 7.4Hz, 3H).

Example 44 (25) 2 (R)-(2-methoxyethoxy) methyl-5- (2
-Methoxyethoxy) methoxy-4 (S)-[N- (4
-Cyanophenylcarbonyl) amino] pentanoic acid

Embedded image TLC: Rf 0.16 (chloroform: methanol = 1
9: 1); NMR (CDCl ₃ ): δ 7.91 (d, J = 8.4 Hz, 2H), 7.71
(d, J = 8.4Hz, 2H), 7.20 (d, J = 8.7Hz, 1H), 4.75
(d, J = 6.9Hz, 1H), 4.70 (d, J = 6.9Hz, 1H), 4.42-
4.31 (m, 1H), 3.84 (dd, J = 10.5, 3.9Hz, 1H), 3.78
-3.60 (m, 7H), 3.57-3.50 (m, 4H), 3.36 (s, 3H), 3.3
2 (s, 3H), 2.82-2.72 (m, 1H), 2.18 (ddd, J = 14.4,
10.2, 7.2Hz, 1H), 1.85 (dt, J = 14.4, 5.7Hz, 1H).

Example 44 (26) 2 (R)-(2-methoxyethoxy) methyl-5-ethoxymethoxy-4 (S)-[N- (4-chlorophenylcarbonyl) amino] pentanoic acid

Embedded image TLC: Rf 0.31 (chloroform: methanol = 9:
1); NMR (CDCl ₃ ): δ 7.72 (d, J = 8.8 Hz, 2H), 7.39
(d, J = 8.8Hz, 2H), 6.84 (d, J = 9.0Hz, 1H), 4.70
(d, J = 7.0Hz, 1H), 4.66 (d, J = 7.0Hz, 1H), 4.43-
4.27 (m, 1H), 3.78-3.50 (m, 10H), 3.35 (s, 3H), 2.
82-2.69 (m, 1H), 2.19 (ddd, J = 14.4, 10.6, 7.4Hz,
1H), 1.82 (ddd, J = 14.4, 5.6, 4.4Hz, 1H), 1.19
(t, J = 7.2Hz, 3H).

Example 44 (27) 2 (S)-(2-propynyl) -5- (2-methoxyethoxy) methoxy-4 (S)-[N- (4-cyanophenylcarbonyl) amino] pentanoic acid

Embedded image TLC: Rf 0.37 (chloroform: methanol = 9:
1); NMR (CDCl ₃ ): δ 7.92 (d, J = 8.7 Hz, 2H), 7.69
(d, J = 8.7 Hz, 2H), 7.17 (d, J = 9.0 Hz, 1H), 4.
77 (d, J = 7.1 Hz, 1H), 4.71 (d, J = 7.1 Hz, 1H),
4.48-4.32 (m, 1H), 3.89 (dd, J = 10.5, 3.6 Hz, 1
H), 3.82-3.60 (m, 3H), 3.55 (t, J = 4.5 Hz, 2H),
3.31 (s, 3H), 2.78-2.50 (m, 3H), 2.25-2.10 (m, 1H),
2.10-1.95 (m, 2H).

Examples 44 (28) to 44 (29) Example 37 → Example 39 → Example 41 (corresponding to methoxymethyl chloride in place of the compound prepared in Reference Example 4 ) The compound was used.) → Example 43 (Using the corresponding compound in place of benzyl bromide) → Example 5 → The same procedure as shown in Example 44 was performed to obtain the compound shown below.

Example 44 (28) 2 (S) -Methyl-5-ethoxymethoxy-4 (S)-
[N-methyl-N- (4-bromophenylcarbonyl)
Amino] pentanoic acid

Embedded image TLC: Rf 0.23 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 12.15 (1H, brs), 7.63-7.56
(2H, m), 7.34-7.25 (2H, m), 4.82-4.72 & 3.79-3.69 (1
H, m), 4.59 & 4.55 (2H, s), 3.61-3.37 (4H, m), 2.76 &
2.64 (3H, s), 2.08 (1H, sxt, J = 6.9Hz), 2.01-1.91
& 1.51-1.41 & 1.37-1.27 (2H, m), 1.14-1.04 (3H, m),
0.82 (3H, d, J = 6.9Hz).

Example 44 (29) 2 (S) -Methyl-5-ethoxymethoxy-4 (S)-
[N-methyl-N- (4-nitrophenylcarbonyl)
Amino] pentanoic acid

Embedded image TLC: Rf 0.42 (chloroform: methanol = 9:
1); NMR (CDCl ₃ ): δ 8.27 and 8.25 (d and d, J = 8)
7Hz and J = 8.7Hz, 2H), 7.68 and 7.58 (d and d, J
= 8.7Hz and J = 8.7Hz, 2H), 5.10-4.98 and 3.92-3.80
(m and m, 1H), 4.76-4.63 (m, 2H), 3.72-3.42 (m, 4
H), 2.96 and 2.80 (s and s, 3H), 2.62-2.50 and 2.27
-2.21 (m and m, 1H), 2.12 and 1.59 (ddd and ddd, J
= 14.4, 10.5, 6.3Hz and 14.4, 7.5, 4.2Hz, 1H), 2.0
2 and1.41 (dt and dt, J = 14.4, 9.0Hz and 14.4, 5.
4Hz, 1H), 1.32 and 1.08 (dand d, J = 7.2Hz and 6.9
Hz, 3H), 1.23 and 1.22 (t and t, J = 7.2 and 7.2H
z, 3H).

Example 45 4 (S) -t-butyldimethylsilyloxymethyl-4
-(N- (4- (benzofuran-2-yl) phenylcarbonyl) amino) butanoic acid methyl ester

Embedded image Imidazole (0.107 g) was added to a solution of the compound prepared in Example 39 (0.294 g) in dimethylformamide (5 ml).
And t-butyldimethylsilyl chloride (0.241 g) were added. The reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was diluted with ethyl acetate, washed with water and a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography (n-hexane: ethyl acetate = 3: 1) to give the title compound (0.361 g) having the following physical data. TLC: Rf 0.83 (n-hexane: ethyl acetate = 1:
1); NMR (CDCl ₃ ): δ 7.94 (2H, d, J = 8.8 Hz), 7.84
(2H, d, J = 8.8Hz), 7.63-7.52 (2H, m), 7.37-7.20 (3
H, m), 7.13 (1H, d, J = 0.8Hz), 6.62 (1H, d, J = 8.8H
z), 4.30-4.16 (1H, m), 3.74 (2H, d, J = 3.6Hz), 3.64
(3H, s), 2.59-2.38 (2H, m), 2.10-1.92 (2H, m), 0.
92 (9H, s), 0.086 (3H, s), 0.066 (3H, s).

Example 46 2 (S) -benzyl-4 (S) -t-butyldimethylsilyloxymethyl-4- (N- (4- (benzofuran-
2-yl) phenylcarbonyl) amino) butanoic acid methyl ester

Embedded image The title compound having the following physical data was obtained by operating in the same manner as in the method shown in Example 42, using the compound produced in Example 45 instead of the compound produced in Example 41. TLC: Rf 0.43 (n-hexane: ethyl acetate = 7:
3); NMR (CDCl ₃ ): δ 7.93 (2H, d, J = 8.4 Hz), 7.83
(2H, d, J = 8.4Hz), 7.63-7.50 (2H, m), 7.38-7.10 (8
H, m), 6.35 (1H, d, J = 8.8Hz), 4.36-4.17 (1H, m), 3.
74-3.60 (2H, m), 3.43 (3H, s), 3.02-2.68 (3H, m),
2.20-2.00 (1H, m), 1.90-1.74 (1H, m), 0.88 (9H, s),
0.038 (3H, s), 0.026 (3H, s).

Example 47 2 (S) -benzyl-4 (S) -tert-butyldimethylsilyloxymethyl-4- (N- (4- (benzofuran-
2-yl) phenylcarbonyl) amino) butanoic acid

Embedded image The title compound having the following physical data was obtained in the same manner as in the method shown in Example 2, except that the compound produced in Example 46 was used instead of the compound produced in Example 1. TLC: Rf 0.44 (chloroform: methanol = 1
9: 1); NMR (CD ₃ OD): δ 7.97 (2H, d, J = 8.4 Hz), 7.90
(2H, d, J = 8.4Hz), 7.63-7.49 (2H, m), 7.37-7.10 (8
H, m), 4.35-4.18 (1H, m), 3.74-3.60 (2H, m), 3.05-
2.82 (2H, m), 2.80-2.64 (1H, m), 1.93 (2H, m), 0.8
7 (9H, s), 0.048 (6H, s).

Example 48 2 (R) -benzyl-4 (S) -hydroxymethyl-4
-(N- (4- (benzofuran-2-yl) phenylcarbonyl) amino) butanoic acid

Embedded image A solution of the compound prepared in Example 47 (0.162 g) in tetrahydrofuran (5 ml) was added at room temperature to a solution of 1 M tetrabutylammonium fluoride in tetrahydrofuran (0.4
ml) was added. The reaction mixture was stirred at room temperature for 2 hours.
Water was added to the reaction mixture, and extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography (n-hexane: ethyl acetate = 9: 1-
1: 9) to give the title compound (0.088 g) having the following physical data. TLC: Rf 0.22 (chloroform: methanol = 1
9: 1); NMR (CD ₃ OD): δ 7.92 (4H, s), 7.60-7.42 (2H,
m), 7.38-7.06 (8H, m), 4.40-4.20 (1H, m), 3.64 (2
H, d, J = 5.4Hz), 3.02-2.82 (2H, m), 2.80-2.62 (1H,
m), 2.10-1.75 (2H, m).

Example 48 (1) 2 (S) -benzyl-4 (S) -hydroxymethyl-4
-(N- (4- (3-methoxy-1-propynyl) phenylcarbonyl) amino) butanoic acid

Embedded image Using the corresponding acid halide in place of the compound prepared in Reference Example 4, operating in the same manner as in the method shown in Example 37 → Example 39 → Example 45 → Example 46 → Example 47 → Example 48, The title compound having the following physical data was obtained. TLC: Rf 0.21 (chloroform: methanol = 1
9: 1).

Example 49 N-hydroxy-4 (S)-(morpholin-1-yl)
Carbonyl-4- (N- (4- (benzofuran-2-yl) phenylcarbonyl) amino) butyramide

Embedded image Using the compound prepared in Example 38 in place of the compound prepared in Example 2, and operating in the same manner as in the method shown in Example 3 → Example 4, the title compound having the following physical data was obtained. TLC: Rf 0.39 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.42 (1H, s), 8.75 (1H, d,
J = 7.6Hz), 8.04 (4H, s), 7.74-7.57 (3H, m), 7.42-7.
25 (2H, m), 5.00-4.82 (1H, m), 3.71-3.40 (8H, m),
2.19-1.82 (4H, m).

Examples 49 (1) to 49 (8) Instead of the compound prepared in Example 38, Examples 40, 42, 44 and 44 (1) to 44 were used.
(3), using the compound prepared in Example 48 and Example 48 (1), in the same manner as in the method shown in Example 49,
The following compounds were obtained.

Example 49 (1) N-hydroxy-4 (S) -hydroxymethyl-4-
(N- (4- (benzofuran-2-yl) phenylcarbonyl) amino) butyramide

Embedded image TLC: Rf 0.22 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.36 (1H, d, J = 1.5 Hz), 8.6
7 (1H, d, J = 1.5Hz), 8.19 (1H, d, J = 8.4Hz), 8.00 (4
H, s), 7.73-7.61 (2H, m), 7.57 (1H, d, J = 0.8Hz),
7.42-7.23 (2H, m), 4.73 (1H, t, J = 5.8Hz), 4.08-3.8
5 (1H, m), 3.58-3.38 (2H, m), 2.12-1.60 (4H, m).

Example 49 (2) N-hydroxy-4 (S) -methoxymethyloxymethyl-4- (N- (4- (benzofuran-2-yl) phenylcarbonyl) amino) butyramide

Embedded image TLC: Rf 0.47 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.37 (1H, s), 8.34 (1H, d,
J = 8.4Hz), 8.00 (4H, s), 7.73-7.61 (2H, m), 7.56 (1
H, s), 7.41-7.24 (2H, m), 4.58 (2H, s), 4.23-4.04
(1H, m), 3.62-3.44 (2H, m), 3.26 (3H, s), 2.12-1.6
2 (4H, m).

Example 49 (3) N-hydroxy-2 (S) -benzyl-4 (S) -methoxymethyloxymethyl-4- (N- (4- (benzofuran-2-yl) phenylcarbonyl) amino) Butyramide

Embedded image TLC: Rf 0.35 (chloroform: methanol = 1
9: 1); NMR (d ₆ -DMSO): δ 10.37 (1H, s), 8.69 (1H,
s), 8.25 (1H, d, J = 8.6Hz), 8.01 (4H, s), 7.72-7.61
(2H, m), 7.57 (1H, s), 7.41-7.09 (7H, m), 4.55 (2
H, s), 4.40-4.20 (1H, m), 3.53 (2H, d, J = 5.6Hz),
3.22 (3H, s), 2.79 (2H, d, J = 7.4Hz), 2.50-2.34 (1
H, m), 1.90-1.60 (2H, m).

Example 49 (4) N-hydroxy-2 (S) -methyl-4 (S) -methoxymethyloxymethyl-4- (N- (4- (benzofuran-2-yl) phenylcarbonyl) amino) Butyramide

Embedded image TLC: Rf 0.23 (chloroform: methanol = 1
9: 1); NMR (d ₆ -DMSO): δ 10.41 (1H, d, J = 1.6 Hz), 8.6
8 (1H, d, J = 1.6Hz), 8.20 (1H, d, J = 8.4Hz), 8.00 (4
H, s), 7.74-7.60 (2H, m), 7.56 (1H, d, J = 0.8Hz),
7.41-7.22 (2H, m), 4.58 (2H, s), 4.32-4.10 (1H,
m), 3.62-3.41 (2H, m), 3.25 (3H, s), 2.30-2.14 (1
H, m), 1.82-1.58 (2H, m), 1.05 (3H, d, J = 6.6Hz).

Example 49 (5) N-hydroxy-2 (S)-(3-phenyl-2-propenyl) -4 (S) -methoxymethyloxymethyl-4
-(N- (4- (benzofuran-2-yl) phenylcarbonyl) amino) butyramide

Embedded image TLC: Rf 0.36 (chloroform: methanol = 1
9: 1); NMR (d ₆ -DMSO): δ 10.50 (1H, s), 8.78 (1H,
s), 8.25 (1H, d, J = 8.4Hz), 8.00 (4H, s), 7.67 (2H,
t, J = 8.6Hz), 7.56 (1H, s), 7.40-7.14 (7H, m), 6.4
1 (1H, d, J = 16.0Hz), 6.15 (1H, dt, J = 16.0, 5.8Hz),
4.57 (2H, s), 4.32-4.14 (1H, m), 3.62-3.45 (2H,
m), 3.24 (3H, s), 2.46-2.22 (3H, m), 1.96-1.78 (2
H, m).

Example 49 (6) N-hydroxy-2 (S)-(3-phenylpropyl)
-4 (S) -methoxymethyloxymethyl-4- (N-
(4- (benzofuran-2-yl) phenylcarbonyl) amino) butyramide

Embedded image TLC: Rf 0.35 (chloroform: methanol = 1
9: 1); NMR (d ₆ -DMSO): δ 10.47 (1H, s), 8.82-8.66 (1
H, brs), 8.20 (1H, d, J = 8.4Hz), 7.99 (4H, s), 7.72
-7.61 (2H, m), 7.57 (1H, d, J = 0.6Hz), 7.41-7.10 (7
H, m), 4.57 (2H, s), 4.23-4.02 (1H, m), 3.60-3.42
(2H, m), 3.24 (3H, s), 2.62-2.40 (2H, m), 2.22-2.06
(1H, m), 1.84-1.64 (2H, m), 1.60-1.38 (4H, m).

Example 49 (7) N-hydroxy-2 (R) -benzyl-4 (S) -hydroxymethyl-4- (N- (4- (benzofuran-2-
Yl) phenylcarbonyl) amino) butyramide

Embedded image TLC: Rf 0.37 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.32 (1H, s), 8.68 (1H,
s), 8.08 (1H, d, J = 8.4Hz), 8.02 (4H, s), 7.72-7.62
(2H, m), 7.59 (1H, s), 7.41-7.06 (7H, m), 4.82-4.
66 (1H, m), 4.24-4.04 (1H, m), 3.60-3.36 (2H, m),
2.92-2.66 (2H, m), 2.50-2.30 (1H, m), 1.92-1.52 (2
H, m).

Example 49 (8) N-hydroxy-2 (S) -benzyl-4 (S) -hydroxymethyl-4- (N- (4- (3-methoxy-1-
Propynyl) phenylcarbonyl) amino) butyramide

Embedded image TLC: Rf 0.23 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.28 (1H, brs), 8.62 (1H,
brs), 8.04 (1H, d, J = 8.4Hz), 7.87 (2H, d, J = 8.2H
z), 7.53 (2H, d, J = 8.2Hz), 7.24-7.05 (5H, m), 4.69
(1H, t, J = 5.7Hz), 4.33 (2H, s), 4.18-4.02 (1H,
m), 3.46-3.34 (2H, m), 3.31 (3H, s), 2.75 (2H, d, J
= 7.0Hz), 2.42-2.26 (1H, m), 1.89-1.52 (2H, m).

Example 49 (9) N-hydroxy-5-hydroxy-4 (S)-[N-
[4- (3-Methoxy-1-propynyl) phenylcarbonyl] amino] pentanamide

Embedded image Example 37 → Example 39 → Example 40 → Example 4 using a corresponding compound instead of the compound produced in Reference Example 4.
The title compound having the following physical data was obtained by operating in the same manner as in the method shown in 9. TLC: Rf 0.36 (chloroform: methanol = 4:
1); NMR (d ₆ -DMSO): δ 10.35 (1H, s), 10.18 (1H,
s), 8.18 (1H, d, J = 8.4Hz), 7.88 (2H, d, J = 8.4Hz),
7.55 (2H, d, J = 8.4Hz), 4.53 (2H, s), 4.02-3.84 (1
H, m), 3.73-3.34 (2H, m), 3.35 (3H, s), 2.07-1.59
(4H, m).

Example 49 (10) N-hydroxy-5-hydroxy-4 (R)-[N-
[4- (3-Methoxy-1-propynyl) phenylcarbonyl] amino] pentanamide

Embedded image Using 4 (R) -carboxy-4-aminobutanoic acid methyl ester instead of 4 (S) -carboxy-4-aminobutanoic acid methyl ester and the corresponding compound instead of the compound prepared in Reference Example 4, the procedure was carried out. The title compound having the following physical data was obtained by the same procedure as described in Example 37 → Example 39 → Example 40 → Example 49. TLC: Rf 0.28 (chloroform: methanol: acetic acid: water = 85: 15: 1: 1); NMR (CD ₃ OD): δ 7.83 (2H, d, J = 8.4 Hz), 7.51 (2H,
d, J = 8.4Hz), 4.34 (2H, s), 4.03-4.15 (1H, m), 3.62
(2H, d, J = 5.6Hz), 3.43 (3H, s), 2.19 (2H, t, J = 7.4H
z), 1.77-2.10 (2H, m).

Examples 49 (11) to 49 (21) Example 37 was repeated using the corresponding compound in place of Reference Example 4.
→ Example 38 (using the corresponding amine compound) → The same procedure as in Example 49 was carried out to obtain the following compound.

Example 49 (11 ) N-hydroxy-4 (S)-(4-hydroxybutylcarbamoyl) -4- [N- [4- (3-methoxy-1-
Propynyl) phenylcarbonyl] amino] butyramide

Embedded image TLC: Rf 0.40 (chloroform: methanol = 4:
1); NMR (d ₆ -DMSO): δ 10.41 (1H, s), 8.61 (1H, d,
J = 7.8Hz), 7.98-7.88 (3H, m), 7.55 (2H, d, J = 8.4Hz),
4.44-4.27 (3H, m), 3.38 (2H, t, J = 6.2Hz), 3.35 (3
H, s), 3.13- 3.00 (2H, m), 2.09-1.83 (4H, m), 1.48
-1.34 (4H, m).

Example 49 (12) N-hydroxy-4 (S)-(3-phenylpropylcarbamoyl) -4- [N- [4- (3-methoxy-1-
Propynyl) phenylcarbonyl] amino] butyramide

Embedded image TLC: Rf 0.38 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.41 (1H, s), 8.72 (1H, s),
8.64 (1H, d, J = 7.6Hz), 8.04-7.94 (1H, m), 7.92 (2
(H, d, J = 8.5Hz), 7.55 (2H, d, J = 8.5Hz), 7.32-7.14
(5H, m), 4.43-4.35 (3H, m), 3.33 (3H, s), 3.16-3.0
2 (2H, m), 2.62-2.49 (2H, m), 2.14-1.84 (4H, m),
1.80-1.62 (2H, m).

Example 49 (13) N-hydroxy-4 (S) -propylcarbamoyl-4
-[N- [4- (3-methoxy-1-propynyl) phenylcarbonyl] amino] butyramide

Embedded image TLC: Rf 0.23 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.40 (1H, s), 8.71 (1H, s),
8.61 (1H, d, J = 7.8Hz), 7.96-7.88 (3H, m), 7.55 (2
H, d, J = 8.3Hz), 4.43-4.26 (3H, m), 3.32 (3H, s),
3.09-2.95 (2H, m), 2.07-1.79 (4H, m), 1.41 (2H, se
xtet, J = 7.3Hz), 0.83 (3H, t, J = 7.3Hz).

Example 49 (14) N-hydroxy-4 (S)-(2-hydroxyethylcarbamoyl) -4- [N- [4- (3-methoxy-1-
Propynyl) phenylcarbonyl] amino] butyramide

Embedded image TLC: Rf 0.09 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.39 (1H, s), 8.71 (1H, s),
8.63 (1H, d, J = 7.6Hz), 7.97-7.87 (3H, m), 7.56 (2
H, d, J = 8.2Hz), 4.66 (1H, t, J = 5.4Hz), 4.43-4.35
(3H, m), 3.40 (2H, m), 3.33 (3H, s), 3.19-3.08 (2
H, m), 2.09-1.83 (4H, m).

Example 49 (15 ) N-hydroxy-4 (S)-(6-hydroxyhexylcarbamoyl) -4- [N- [4- (3-methoxy-1
-Propynyl) phenylcarbonyl] amino] butyramide

Embedded image TLC: Rf 0.42 (chloroform: methanol = 4:
1); NMR (d ₆ -DMSO): δ 10.37 (1H, s), 8.68 (1H, s),
8.57 (1H, d, J = 7.6Hz), 7.93-7.83 (3H, m), 7.53 (2
H, d, J = 8.4Hz), 4.37-4.25 (4H, m), 3.38-3.29 (5H,
m), 3.09-2.93 (2H, m), 2.12-1.78 (4H, m), 1.43-1.1
5 (8H, m).

Example 49 (16) N-hydroxy-4 (S)-[2- (4-methoxyphenyl) ethylcarbamoyl] -4- [N- [4- (3-
Methoxy-1-propynyl) phenylcarbonyl] amino] butyramide

Embedded image TLC: Rf 0.25 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.40 (1H, s), 8.72 (1H, s),
8.62 (1H, d, J = 8.4Hz), 8.00-7.86 (3H, m), 7.60-7.
52 (2H, m), 7.10-7.08 (2H, d, J = 8.4Hz), 6.82-6.79
(2H, d, J = 8.4Hz), 4.40-4.25 (3H, m), 3.70-3.69 (3
H, s), 3.35 (3H, s), 3.36-3.15 (2H, m), 2.63 (2H,
t, J = 7.3Hz), 2.19-1.82 (4H, m).

Example 49 (17) N-hydroxy-4 (S)-(2-morpholinoethylcarbamoyl) -4- [N- [4- (3-methoxy-1-)
Propynyl) phenylcarbonyl] amino] butyramide

Embedded image TLC: Rf 0.70 (chloroform: methanol = 4:
1); NMR (d ₆ -DMSO): δ 10.32 (1H, s), 8.60 (1H, d,
J = 7.6Hz), 8.32 (1H, s), 7.92 (2H, d, J = 8.4Hz), 7.83
(1H, t, J = 5.5Hz), 7.56 (2H, d, J = 8.4Hz), 4.42-4.30
(3H, m), 3.55-3.48 (4H, m), 3.35 (3H, s), 3.23-3.
20 (4H, m), 2.39-2.29 (4H, m), 2.21-1.83 (4H, m).

Example 49 (18) N-hydroxy-4 (S)-[2- (indole-3-
Yl) ethylcarbamoyl) -4- [N- [4- (3-
Methoxy-1-propynyl) phenylcarbonyl] amino] butyramide

Embedded image TLC: Rf 0.33 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.79 (1H, s), 10.41 (1H,
s), 8.64 (1H, d, J = 7.6Hz), 8.12-8.04 (1H, m), 7.92
(2H, d, J = 8.5Hz), 7.61-7.52 (3H, m), 7.32 (1H, d,
J = 7.6Hz), 7.17-6.92 (3H, m), 4.45-4.35 (3H, m),
3.42-3.33 (4H, m), 2.82 (2H, t, J = 7.4Hz), 2.17-1.8
4 (4H, m).

Example 49 (19) N-hydroxy-4 (S)-(4-phenylbutylcarbamoyl) -4- [N- [4- (3-methoxy-1-propynyl) phenylcarbonyl] amino] butyramide

Embedded image TLC: Rf 0.16 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.40 (1H, s), 8.70 (1H, br)
s), 8.62 (1H, d, J = 7.8Hz), 7.98-7.87 (3H, m), 7.55
(2H, d, J = 8.5Hz), 7.30-7.14 (5H, m), 4.40-4.34 (3
H, m), 3.35 (3H, s), 3.09 (2H, q, J = 6.0Hz), 2.56
(2H, t, J = 7.0Hz), 2.12-1.83 (4H, m), 1.64-1.34 (4
H, m).

Example 49 (20) N-hydroxy-4 (S)-(2-phenylethylcarbamoyl) -4- [N- [4- (3-methoxy-1-propynyl) phenylcarbonyl] amino] butyramide

Embedded image TLC: Rf 0.36 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.39 (1H, s), 8.72 (1H, s),
8.63 (1H, d, J = 8.0Hz), 8.01 (1H, t, J = 5.7Hz), 7.9
2 (2H, d, J = 8.4Hz), 7.57 (2H, d, J = 8.4Hz), 7.29-7.1
4 (5H, m), 4.39-4.28 (3H, m), 3.35-3.23 (5H, m),
2.71 (2H, t, J = 7.5Hz), 2.09-1.82 (4H, m).

Example 49 (21) N-hydroxy-4 (S)-[3- (pyrazole-1-
Yl) propylcarbamoyl] -4- [N- [4- (3
-Methoxy-1-propynyl) phenylcarbonyl] amino] butyramide

Embedded image TLC: Rf 0.23 (chloroform: methanol: acetic acid = 9: 1: 0.5); NMR (d ₆ -DMSO): δ 10.43 (1H, s), 8.69 (1H, d,
J = 7.5Hz), 8.06 (1H, t, J = 5.6Hz), 7.93 (2H, d, J = 8.4
Hz), 7.71 (1H, d, J = 2.0Hz), 7.56 (2H, d, J = 8.4Hz),
7.42 (1H, d, J = 2.0Hz), 6.21 (1H, t, J = 2.0Hz), 4.3
7-4.27 (3H, m), 4.11 (2H, t, J = 6.8Hz), 3.35 (3H,
s), 3.09-2.99 (2H, m), 2.12-1.86 (6H, m).

Example 49 (22) N-hydroxy-4 (R)-(3-phenylpropylcarbamoyl) -4- [N- [4- (3-methoxy-1-
Propynyl) phenylcarbonyl] amino] butyramide

Embedded image Example 37 → Example using 4 (R) -carboxy-4-aminobutanoic acid methyl ester instead of 4 (S) -carboxy-4-aminobutanoic acid methyl ester and the corresponding compound in place of Reference Example 4 38 (using the corresponding amine compound) → The same procedure as in Example 49 was carried out to give the title compound having the following physical data. TLC: Rf 0.44 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.39 (1H, brs), 8.70 (1H, br)
s), 8.63 (1H, d, J = 7.8Hz), 7.98 (1H, t, J = 5.6Hz), 7.
90 (2H, d, J = 8.4Hz), 7.54 (2H, d, J = 8.4Hz), 7.10-7.2
8 (5H, m), 4.42-4.35 (3H, m), 3.32 (3H, s), 3.11-3.01
(2H, m), 2.57-2.47 (2H, m), 2.13-1.82 (4H, m), 1.74-
1.60 (2H, m).

Example 49 (23) N-hydroxy-2- (pyridin-3-yl) methyl-
4- (2-phenylethylcarbamoyl) -4- [N-
(4-phenoxyphenylcarbonyl) amino] butyramide

Embedded image Instead of 4 (S) -carboxy-4-aminobutanoic acid methyl ester, 4 (S) -t-butoxycarbonyl-
Example 43 → Example 27 → Example 37 using methyl 4- (N-benzyloxycarbonylamino) butanoate and the corresponding compound in place of benzyl bromide
(Use the corresponding compound in place of Reference Example 4.) → Example 14 → Example 38 (using the corresponding amine compound) → Operate in the same manner as described in Example 49 and have the following physical data. The title compound was obtained. TLC: Rf 0.30, 0.36 (chloroform: methanol: acetic acid = 9: 1: 0.5); NMR (d ₆ -DMSO / MeOH): δ 8.33-8.26 (2H, m), 7.89
-7.82 (2H, m), 7.48 (1H, t, J = 8.1Hz), 7.39-7.31 (2
H, m), 7.24-7.06 (5H, m), 7.02-6.90 (6H, m), 4.48
(1H of 2 isomers, dd, J = 5.0Hz, 10.1Hz), 4.29 (1H o
f 2 isomers, dd, J = 4.2Hz, 10.5Hz), 3.20-3.02 (2H,
m), 2.95-2.84 (1H of 2 isomers, m), 2.79-2.57 (1H
of 2 isomers + 2H, m), 2.51-2.27 (2H, m), 2.04-1.9
2 (2H of 2 isomers, m), 1.88-1.77 (2H of 2 isomers, m)
s, m).

Examples 49 (24) to 49 (35) Example 37 was repeated using the corresponding compound in place of Reference Example 4.
→ Example 39 → Example 41 (in some cases, a corresponding compound may be used in place of methoxymethyl chloride) → Example 42 → The same procedure as shown in Example 49 is carried out.
The following compounds were obtained.

Example 49 (24) N-hydroxy-5-methoxymethoxy-4 (S)-
[N- [4- (3-methoxy-1-propynyl) phenylcarbonyl] amino] pentanamide

Embedded image TLC: Rf 0.22 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.35 (1H, s), 8.32 (1H, d,
J = 8.6Hz), 7.87 (2H, d, J = 8.4Hz), 7.55 (2H, d, J = 8.4
Hz), 4.57 (2H, s), 4.36 (2H, s), 4.20-4.01 (1H,
m), 3.55-3.44 (2H, m), 3.35 (3H, s), 3.24 (3H, s),
2.09-1.64 (4H, m).

Example 49 (25) N-hydroxy-5-benzyloxymethoxy-4
(S)-[N- [4- (3-methoxy-1-propynyl) phenylcarbonyl] amino] pentanamide

Embedded image TLC: Rf 0.24 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.37 (1H, s), 8.36 (1H, d,
J = 8.8Hz), 7.88 (2H, d, J = 8.5Hz), 7.55 (2H, d, J = 8.5
Hz), 7.37-7.26 (5H, m), 4.72 (2H, s), 4.53 (2H,
s), 4.35 (2H, s), 4.22-4.07 (1H, m), 3.63-3.55 (2
H, m), 3.35 (3H, s), 2.09-1.68 (4H, m).

Example 49 (26) N-hydroxy-5- (2-methoxyethoxy) methoxy-4 (S)-[N- [4- (3-phenoxy-1-propynyl) phenylcarbonyl] amino] pentanamide

Embedded image TLC: Rf 0.41 (chloroform: methanol: acetic acid: water = 100: 10: 1: 1); NMR (d ₆ -DMSO): δ 10.32 (1H, s), 8.65 (1H, s),
8.30 (1H, d, J = 8.6Hz), 7.84 (2H, d, J = 8.4Hz), 7.52 (2
H, d, J = 8.4Hz), 7.28-7.36 (2H, m), 6.93-7.06 (3H,
m), 5.04 (2H, s), 4.60 (2H, s), 3.95-4.16 (1H, m), 3.
38-3.56 (6H, m), 3.19 (3H, s), 1.57-2.08 (4H, m).

Example 49 (27) N-hydroxy-5-methoxymethoxy-4 (S)-
[N- [4- (3-phenoxy-1-propynyl) phenylcarbonyl] amino] pentanamide

Embedded image TLC: Rf 0.27 (chloroform: methanol: acetic acid: water = 100: 10: 1: 1); NMR (d ₆ -DMSO): δ 10.31 (1H, brs), 8.69 (1H, br)
s), 8.29 (1H, brs), 7.83 (2H, d, J = 8.7Hz), 7.51 (2H,
d, J = 8.4Hz), 7.16 (2H, t, J = 8.0Hz), 7.03 (2H, d, J = 8.
7Hz), 6.97 (1H, t, J = 7.5Hz), 5.05 (2H, s), 4.54 (2H,
s), 3.98-4.13 (1H, m), 3.42-3.52 (2H, m), 3.21 (3H,
s), 1.62-2.02 (4H, m).

Example 49 (28) N-hydroxy-5-benzyloxymethoxy-4
(S)-[N- [4- (3-phenoxy-1-propynyl) phenylcarbonyl] amino] pentanamide

Embedded image TLC: Rf 0.47 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.34 (1H, s), 8.67 (1H, s),
8.35 (1H, d, J = 8.0Hz), 7.85 (2H, d, J = 8.4Hz), 7.52 (2
H, d, J = 8.4Hz), 7.37-7.25 (7H, m), 7.07-6.94 (3H,
m), 5.06 (2H, s), 4.70 (2H, s), 4.51 (2H, s), 4.01-3.
98 (1H, m), 3.56 (2H, d, J = 6.0Hz), 2.09-1.58 (4H,
m).

Example 49 (29) N-hydroxy-5-methoxymethoxy-4 (S)-
[N- (4-phenoxyphenylcarbonyl) amino]
Pentanamide

Embedded image TLC: Rf 0.36 (chloroform: methanol: acetic acid: water = 100: 10: 1: 1); NMR (d ₆ -DMSO): δ 10.33 (1H, s), 8.66 (1H, s),
8.16 (1H, d, J = 8.4Hz), 7.87 (2H, d, J = 8.8Hz), 7.46-7.
38 (2H, m), 7.22-7.15 (2H, m), 7.07-6.99 (3H, m), 4.54
(2H, s), 4.19-3.94 (1H, m), 3.49-3.45 (2H, m), 3.22
(3H, s), 2.07-1.57 (4H, m).

Example 49 (30) N-hydroxy-5-methoxymethoxy-4 (S)-
[N- [4- (4-chlorophenyl) phenylcarbonyl] amino] pentanamide

Embedded image TLC: Rf 0.28 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.37 (1H, s), 8.31 (1H, d,
J = 8.2Hz), 7.97 (2H, d, J = 8.6Hz), 7.81-7.75 (4H, m),
7.55 (2H, d, J = 8.6Hz), 4.58 (2H, s), 4.19-4.03 (1
H, m), 3.56-3.49 (2H, m), 3.25 (3H, s), 2.09-1.77
(4H, m).

Example 49 (31) N-hydroxy-5-methoxymethoxy-4 (S)-
[N- [4- [2- (4-methylphenyl) ethynyl]]
Phenylcarbonyl] amino] pentanamide

Embedded image TLC: Rf 0.37 (chloroform: methanol: acetic acid: water = 100: 10: 1: 1); NMR (d ₆ -DMSO): δ 10.35 (1H, brs.), 8.67 (1H, br)
s.), 8.33 (1H, d, J = 8.6Hz), 7.89 (2H, d, J = 8.4Hz),
7.62 (2H, d, J = 8.4Hz), 7.47 (2H, d, J = 8.2Hz), 7.25 (2H, d, J = 8.2Hz)
H, d, J = 8.2Hz), 4.56 (2H, s), 4.19-3.98 (1H, m), 3.5
6-3.42 (2H, m), 3.23 (3H, s), 2.34 (3H, s), 2.09-1.58
(4H, m).

Example 49 (32) N-hydroxy-5-methoxymethoxy-4 (S)-
[N- [4- [2E- (4-chlorophenyl) ethenyl] phenylcarbonyl] amino] pentanamide

Embedded image TLC: Rf 0.38 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.35 (1H, brs.), 8.67 (1H, br)
s.), 8.23 (1H, d, J = 8.6Hz), 7.87 (2H, d, J = 8.2Hz),
7.68 (2H, d, J = 8.4Hz), 7.66 (2H, d, J = 8.4Hz), 7.41 (2
H, d, J = 8.2Hz), 7.40 (1H, d, J = 17.8Hz), 7.31 (1H, d,
J = 17.8Hz), 4.56 (2H, s), 4.19-3.98 (1H, m), 3.58-3.
41 (2H, m), 3.23 (3H, s), 2.11-1.56 (4H, m).

Example 49 (33) N-hydroxy-5-methoxymethoxy-4 (S)-
[N- [4- (1-heptynyl) phenylcarbonyl]
Amino] pentanamide

Embedded image TLC: Rf 0.46 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.34 (1H, s), 8.67 (1H, s),
8.27 (1H, d, J = 8.4Hz), 7.82 (2H, d, J = 8.2Hz), 7.45 (2
H, d, J = 8.2Hz), 4.55 (2H, s), 4.18-3.97 (1H, m), 3.57
-3.41 (2H, m), 3.22 (3H, s), 2.49-2.40 (2H, m), 2.04-
1.22 (10H, m), 0.88 (3H, t, J = 6.8Hz).

Example 49 (34) N-hydroxy-5-ethoxymethoxy-4 (S)-
[N- (4-phenoxyphenylcarbonyl) amino]
Pentanamide

Embedded image TLC: Rf 0.34 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.36 (s, 1H), 8.68 (s, 1H),
8.17 (d, J = 8.4Hz, 1H), 7.89 (d, J = 8.9Hz, 2H), 7.
43 (dd, J = 8.5, 7.5Hz, 2H), 7.20 (t, J = 7.5Hz, 1
H), 7.07 (dd, J = 1.1, 8.5Hz, 2H), 7.03 (d, J = 8.9H
z, 2H), 4.61 (s, 2H), 4.15-4.00 (m, 1H), 3.60-3.40
(m, 4H), 2.10-1.95 (m, 2H), 1.95-1.80 (m, 1H), 1.
80-1.60 (m, 1H), 1.11 (t, J = 7.1Hz, 3H).

Example 49 (35) N-hydroxy-5-ethoxymethoxy-4 (S)-
[N- (4-methylphenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.30 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.32 (s, 1H), 8.65 (s, 1H),
8.10 (d, J = 8.4Hz, 1H), 7.73 (d, J = 8.3Hz, 2H), 7.
22 (d, J = 8.3Hz, 2H), 4.57 (s, 2H), 4.10-3.98 (m, 1
H), 3.52-3.40 (m, 4H), 2.32 (s, 3H), 2.01-1.94 (m,
2H), 1.91-1.78 (m, 1H), 1.73-1.61 (m, 1H), 1.05
(t, J = 7.1Hz, 3H).

Example 49 (36) N-hydroxy-5-methoxymethoxy-4 (R)-
[N- [4- (3-methoxy-1-propynyl) phenylcarbonyl] amino] pentanamide

Embedded image Example 37 → Example using 4 (R) -carboxy-4-aminobutanoic acid methyl ester instead of 4 (S) -carboxy-4-aminobutanoic acid methyl ester and the corresponding compound in place of Reference Example 4 39 → Example 4
The title compound having the following physical properties was obtained in the same manner as in the method shown in 1 → Example 42 → Example 49. TLC: Rf 0.25 (chloroform: methanol: acetic acid: water = 100: 10: 1: 1); NMR (CD ₃ OD): δ 8.32 (1H, d, J = 8.8 Hz), 7.82 (2
H, d, J = 8.8Hz), 7.52 (2H, d, J = 8.8Hz), 4.62 (2H,
s), 4.34 (2H, s), 4.16-4.31 (1H, m), 3.62 (2H, d,
J = 5.6Hz), 3.43 (3H, s), 3.33 (3H, s), 2.20 (2H, t,
J = 7.0Hz), 1.17-2.11 (2H, m).

Examples 49 (37) to 49 (67) Using the corresponding compound in place of the compound prepared in Reference Example 4, Example 37 → Example 39 → Example 41 → Example 4
3 (use methyl iodide instead of benzyl bromide)
→ Example 44 → The same procedure as in Example 49 was performed to obtain the following compound.

Example 49 (37) N-hydroxy-2 (S) -methyl-5-methoxymethoxy-4 (S)-[N- [4- [2- (4-imidazolylphenyl) ethynyl] phenylcarbonyl] amino]
Pentanamide

Embedded image TLC: Rf 0.33 (chloroform: methanol = 1
0: 1); NMR (d ₆ -DMSO): δ 10.40 (1H, brs), 8.68 (1H, b
rs), 8.36 (1H, s), 8.24 (1H, d, J = 9.0Hz), 7.91 (2
H, d, J = 8.4Hz), 7.84 (1H, brs), 7.77 (2H, d, J = 9.0
Hz), 7.72 (2H, d, J = 9.0Hz), 7.66 (2H, d, J = 8.4Hz),
7.13 (1H, brs), 4.56 (2H, s), 4.22-4.11 (1H, m),
3.54-3.44 (2H, m), 3.23 (3H, s), 2.25-2.14 (1H,
m), 1.76-1.61 (2H, m), 1.03 (3H, d, J = 6.6Hz).

Example 49 (38) N-hydroxy-2 (S) -methyl-5-methoxymethoxy-4 (S)-[N- [4- (4-phenyl-1,
2,5,6-tetrahydropyridin-1-yl) phenylcarbonyl] amino] pentanamide

Embedded image TLC: Rf 0.32 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.39 (1H, brs), 8.67 (1H, b
rs), 7.90-7.70 (3H, m), 7.49 (2H, d, J = 7.5Hz), 7.37
(2H, t, J = 7.5Hz), 7.27 (1H, t, J = 7.5Hz), 6.99 (2H, t, J = 7.5Hz)
d, J = 9.0Hz), 6.35-6.25 (1H, brs), 4.56 (2H, s),
4.25-4.05 (1H, m), 4.00-3.90 (2H, m), 3.59 (2H, t,
J = 5.4Hz), 3.55-3.40 (2H, m), 3.24 (3H, s), 2.70-2.
55 (2H, m), 2.30-2.10 (1H, m), 1.80-1.60 (2H, m),
1.03 (3H, d, J = 6.9Hz).

Example 49 (39) N-hydroxy-2 (S) -methyl-5-methoxymethoxy-4 (S)-[N- (4-phenoxyphenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.49 (chloroform: methanol: acetic acid: water = 100: 10: 1: 1); NMR (d ₆ -DMSO): δ 10.38 (1H, d, J = 1.5 Hz), 8.66
(1H, d, J = 1.5Hz), 8.05 (1H, d, J = 8.4Hz), 7.88 (2H,
d, J = 8.7Hz), 7.45-7.40 (2H, m), 7.22-7.17 (1H, m), 7.
08-7.01 (4H, m), 4.55 (2H, s), 4.21-4.08 (1H, m), 3.5
2-3.44 (2H, m), 3.22 (3H, s), 2.25-2.09 (1H, m), 1.67
(2H, t, J = 7.2Hz), 1.01 (3H, d, J = 6.6Hz).

Example 49 (40) N-hydroxy-2 (S) -methyl-5-methoxymethoxy-4 (S)-[N- [4- [2- (4-chlorophenyl) ethenyl] phenylcarbonyl] amino ] Pentanamide

Embedded image TLC: Rf 0.41 (chloroform: methanol: acetic acid: water = 100: 10: 1: 1); NMR (d ₆ -DMSO): δ 10.39 (1H, s), 8.67 (1H, s),
8.10 (1H, d, J = 8.6Hz), 7.86 (2H, d, J = 8.4Hz), 7.70-7.
63 (4H, m), 7.45 (2H, d, J = 8.6Hz), 7.40 (1H, d, J = 16.6
Hz), 7.31 (1H, d, J = 16.6Hz), 4.56 (2H, s), 4.25-4.08
(1H, m), 3.57-3.41 (2H, m), 3.23 (3H, s), 2.25-2.15
(1H, m), 1.68 (2H, t, J = 6.6Hz), 1.02 (3H, d, J = 7.0H
z).

Example 49 (41) N-hydroxy-2 (S) -methyl-5-methoxymethoxy-4 (S)-[N- [4- (4-propylphenyl) phenylcarbonyl] amino] pentanamide

Embedded image TLC: Rf 0.31 (chloroform: methanol = 1
0: 1); NMR (d ₆ -DMSO): δ 10.39 (1H, brs), 8.67 (1H, b
rs), 8.14 (1H, d, J = 8.7Hz), 7.93 (2H, d, J = 8.4Hz),
7.73 (2H, d, J = 8.4Hz), 7.63 (2H, d, J = 8.1Hz), 7.3
0 (2H, d, J = 8.1Hz), 4.56 (2H, s), 4.24-4.12 (1H,
m), 3.55-3.44 (2H, m), 3.23 (3H, s), 2.59 (2H, t,
J = 7.2Hz), 2.26-2.35 (1H, m), 1.73-1.65 (2H, m), 1.
61 (2H, m), 1.03 (3H, d, J = 6.9Hz), 0.91 (3H, t, J =
7.2Hz).

Example 49 (42) N-hydroxy-2 (S) -methyl-5-methoxymethoxy-4 (S)-[N- [4- (benzothiophene-2
-Yl) phenylcarbonyl] amino] pentanamide

Embedded image TLC: Rf 0.33 (chloroform: methanol = 1
0: 1); NMR (d ₆ -DMSO): δ 10.40 (1H, brs), 8.68 (1H, b
rs), 8.19 (1H, d, J = 9.0Hz), 8.01-7.94 (4H, m), 7.8
8-7.85 (3H, m), 7.44-7.35 (2H, m), 4.57 (2H, s),
4.24-4.12 (1H, m), 3.55-3.45 (2H, m), 3.24 (3H,
s), 2.26-2.15 (1H, m), 1.77-1.62 (2H, m), 1.04 (3
H, d, J = 6.6Hz).

Example 49 (43) N-hydroxy-2 (S) -methyl-5-methoxymethoxy-4 (S)-[N- [4- (3-methoxyphenoxy) phenylcarbonyl] amino] pentanamide

Embedded image TLC: Rf 0.38 (chloroform: methanol: acetic acid: water = 100: 10: 1: 1); NMR (d ₆ -DMSO): δ 10.36 (s, 1H), 8.67 (s, 1H),
7.87 (d, J = 8.8Hz, 2H), 7.32 (m, 1H), 7.05 (d, J =
8.8Hz, 2H), 6.77 (m, 1H), 6.63 (m, 1H), 6.60 (m, 1
H), 4.55 (s, 2H), 4.15 (m, 1H), 3.74 (s, 3H), 3.22
(s, 3H), 2.18 (m, 1H), 1.66 (m, 2H), 1.02 (d, J = 6.
6Hz, 3H).

Example 49 (44) N-hydroxy-2 (S) -methyl-5-methoxymethoxy-4 (S)-[N- [4- (4-methoxyphenoxy) phenylcarbonyl] amino] pentanamide

Embedded image TLC: Rf 0.45 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.50-10.20 (br, 1H), 8.80-
8.50 (br, 1H), 8.01 (d, J = 8.4Hz, 1H), 7.85 (d, J =
8.7Hz, 2H), 7.05 (d, J = 9.2Hz, 2H), 6.99 (d, J = 9.2H
z, 2H), 6.94 (d, J = 8.7Hz, 2H), 4.56 (s, 2H), 4.25-
4.05 (m, 1H), 3.77 (s, 3H), 3.55-3.40 (m, 2H), 3.2
3 (s, 3H), 2.30-2.10 (m, 1H), 1.80-1.60 (m, 2H),
1.02 (d, J = 6.9Hz, 3H).

Example 49 (45) N-hydroxy-2 (S) -methyl-5-methoxymethoxy-4 (S)-[N- (4-benzoylphenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.36 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.38 (1H, s), 8.66 (1H, s),
8.31 (1H, d, J = 8.1Hz), 7.98 (2H, d, J = 8.7Hz), 7.7
9-7.65 (5H, m), 7.55 (2H, t, J = 7.5Hz), 4.55 (2H,
s), 4.24-4.12 (1H, m), 3.52-3.42 (2H, m), 3.21 (3
H, s), 2.25-2.13 (1H, m), 1.71-1.63 (2H, m), 1.01
(3H, d, J = 6.9Hz).

Example 49 (46) N-hydroxy-2 (S) -methyl-5-methoxymethoxy-4 (S)-[N- [4- (naphthalen-2-yl) phenylcarbonyl] amino] pentanamide

Embedded image TLC: Rf 0.31 (chloroform: methanol: acetic acid: water = 100: 10: 1: 1); NMR (d ₆ -DMSO): δ 10.41 (br, 1H), 8.68 (br, 1)
H), 8.30 (s, 1H), 8.05-7.9 (m, 8H), 7.6-7.5 (m, 2
H), 4.58 (s, 2H), 4.20 (m, 1H), 3.51 (m, 2H), 3.24
(s, 3H), 2.01 (m, 1H), 1.72 (m, 2H), 1.04 (d, J =
6.6Hz, 3H).

Example 49 (47) N-hydroxy-2 (S) -methyl-5-methoxymethoxy-4 (S)-[N- [4-[(4-methoxybiphenyl-4'-yl) oxy] Phenylcarbonyl] amino] pentanamide

Embedded image TLC: Rf 0.34 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.60-10.35 (br, 1H), 8.80-
8.60 (br, 1H), 8.11 (d, J = 8.4Hz, 1H), 7.94 (d, J
= 8.4Hz, 2H), 7.66 (d, J = 8.8Hz, 2H), 7.59 (d, J
= 8.8Hz, 2H), 7.20-6.95 (m, 6H), 4.57 (s, 2H), 4.
30-4.10 (m, 1H), 3.81 (s, 3H), 3.60-3.40 (m, 2H),
3.25 (s, 3H), 2.40-2.10 (m, 1H), 1.90-1.60 (m, 2
H), 1.04 (d, J = 6.6 Hz, 3H).

Example 49 (48) N-hydroxy-2 (S) -methyl-5-methoxymethoxy-4 (S)-[N- [4- (4-ethoxyphenyl) phenylcarbonyl] amino] pentanamide

Embedded image TLC: Rf 0.41 (chloroform: methanol = 1
0: 1); NMR (d ₆ -DMSO): δ 10.39 (1H, brs), 8.67 (1H, b
rs), 8.11 (1H, d, J = 8.7Hz), 7.91 (2H, d, J = 8.1Hz),
7.70 (2H, d, J = 8.1Hz), 7.66 (2H, d, J = 8.7Hz), 7.0
2 (2H, d, J = 8.7Hz), 4.56 (2H, s), 4.24-4.12 (1H,
m), 4.07 (2H, q, J = 6.9Hz), 3.54-3.44 (2H, m), 3.23
(3H, s), 2.26-2.34 (1H, m), 1.73-1.65 (2H, m), 1.
34 (3H, t, J = 6.9Hz), 1.03 (3H, d, J = 6.9Hz).

Example 49 (49) N-hydroxy-2 (S) -methyl-5-methoxymethoxy-4 (S)-[N- [4- (4-phenoxyphenyl) phenylcarbonyl] amino] pentanamide

Embedded image TLC: Rf 0.43 (chloroform: methanol = 1
0: 1); NMR (d ₆ -DMSO): δ 10.40 (1H, brs), 8.67 (1H, b
rs), 8.14 (1H, d, J = 8.6Hz), 7.94 (2H, d, J = 8.4Hz),
7.75 (2H, d, J = 8.8Hz), 7.74 (2H, d, J = 8.4Hz), 7.4
6-7.38 (2H, m), 7.21-7.05 (3H, m), 7.10 (2H, d, J =
8.8Hz), 4.57 (2H, s), 4.27-4.10 (1H, m), 3.58-3.42
(2H, m), 3.23 (3H, s), 2.29-2.12 (1H, m), 1.73-1.
66 (2H, m), 1.03 (3H, d, J = 6.6Hz).

Example 49 (50) N-hydroxy-2 (S) -methyl-5-methoxymethoxy-4 (S)-[N- [4- (3-cyanomethylphenyl) phenylcarbonyl] amino] pentanamide

Embedded image TLC: Rf 0.40 (chloroform: methanol = 1
0: 1); NMR (d ₆ -DMSO): δ 10.40 (1H, brs), 8.67 (1H, b
rs), 8.18 (1H, d, J = 8.7Hz), 7.96 (2H, d, J = 8.4Hz),
7.76 (2H, d, J = 8.4Hz), 7.70 (1H, s), 7.69 (1H, d,
J = 7.8Hz), 7.52 (1H, t, J = 7.8Hz), 7.39 (1H, d, J = 7.
8Hz), 4.57 (2H, s), 4.24-4.13 (1H, m), 4.11 (2H,
s), 3.52 (1H, dd, J = 5.3, 9.9Hz), 3.47 (1H, dd, J =
6.0, 9.9Hz), 3.23 (3H, s), 2.27-2.34 (1H, m), 1.77
-1.62 (2H, m), 1.03 (3H, d, J = 6.6Hz).

Example 49 (51 ) N-hydroxy-2 (S) -methyl-5-methoxymethoxy-4 (S)-[N- [4- (biphenyl-4-yl) phenylcarbonyl] amino] pentanamide

Embedded image TLC: Rf 0.26 (chloroform: methanol: acetic acid: water = 100: 10: 1: 1); NMR (d ₆ -DMSO): δ 10.40 (br, 1H), 8.67 (br, 1)
H), 8.18 (d, J = 8.8Hz, 1H), 7.96 (d, J = 8.5Hz, 2
H), 7.85-7.75 (m, 6H), 7.73 (m, 2H), 7.49 (m, 2H),
7.39 (m, 1H), 4.57 (s, 2H), 4.19 (m, 1H), 3.50
(m, 2H), 3.24 (s, 3H), 2.21 (m, 1H), 1.70 (m, 2H),
1.03 (d, J = 6.6 Hz, 3H).

Example 49 (52) N-hydroxy-2 (S) -methyl-5-methoxymethoxy-4 (S)-[N- [4- (3-hydroxyphenoxy) phenylcarbonyl] amino] pentanamide

Embedded image TLC: Rf 0.17 (chloroform: methanol: acetic acid: water = 100: 10: 1: 1); NMR (d ₆ -DMSO): δ 10.32 (br, 1H), 8.67 (br, 1)
H), 8.04 (d, J = 8.8Hz, 1H), 7.87 (d, J = 8.8Hz, 2
H), 7.18 (t, J = 8.2Hz, 1H), 7.02 (d, J = 8.8Hz, 2
H), 6.58 (m, 1H), 6.45 (m, 1H), 6.40 (m, 1H), 4.55
(s, 2H), 4.15 (m, 1H), 3.47 (m, 2H), 3.22 (s, 3H),
2.07 (m, 1H), 1.66 (m, 2H), 1.01 (d, J = 6.9Hz, 3
H).

Example 49 (53) N-hydroxy-2 (S) -methyl-5-methoxymethoxy-4 (S)-[N- [4- [2- (4-methylphenyl) ethynyl] phenylcarbonyl] Amino] pentanamide

Embedded image TLC: Rf 0.23 (chloroform: methanol = 1
9: 1); NMR (d ₆ -DMSO): δ 10.40 (1H, s), 8.21 (1H, d,
J = 8.4Hz), 7.90 (2H, d, J = 8.4Hz), 7.61 (2H, d, J = 8.4
Hz), 7.47 (2H, d, J = 8.0Hz), 7.25 (2H, d, J = 8.0Hz),
4.57 (2H, s), 4.30- 4.10 (1H, m), 3.60-3.40 (2H,
m), 3.24 (3H, s), 2.35 (3H, s), 2.28-2.10 (1H, m),
1.78-1.60 (2H, m), 1.04 (3H, d, J = 7.0Hz).

Example 49 (54) N-hydroxy-2 (S) -methyl-5-methoxymethoxy-4 (S)-[N- [4- (4-hydroxyphenoxy) phenylcarbonyl] amino] pentanamide

Embedded image TLC: Rf 0.23 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.38 (s, 1H), 9.41 (s, 1H),
8.67 (s, 1H), 7.98 (d, J = 8.7Hz, 1H), 7.84 (d, J
= 8.9Hz, 2H), 6.95-6.85 (m, 4H), 6.81 (d, J = 8.9H
z, 2H), 4.56 (s, 2H), 4.25-4.10 (m, 1H), 3.55-3.40
(m, 2H), 3.24 (s, 3H), 2.25-2.10 (m, 1H), 1.70-1.
60 (m, 2H), 1.03 (d, J = 6.9 Hz, 3H).

Example 49 (55) N-hydroxy-2 (S) -methyl-5-methoxymethoxy-4 (S)-[N- [4- (4-chlorophenyl)
Phenylcarbonyl] amino] pentanamide

Embedded image TLC: Rf 0.39 (chloroform: methanol = 1
0: 1); NMR (d ₆ -DMSO): δ 10.40 (1H, d, J = 1.8 Hz), 8.67
(1H, d, J = 1.8Hz), 8.18 (1H, d, J = 8.4Hz), 7.95 (2
H, d, J = 8.4Hz), 7.76 (2H, d, J = 8.4Hz), 7.76 (2H, d,
J = 8.7Hz), 7.54 (2H, d, J = 8.7Hz), 4.56 (2H, s), 4.
24-4.12 (1H, m), 3.55-3.44 (2H, m), 3.23 (3H, s),
2.26-2.14 (1H, m), 1.77-1.62 (2H, m), 1.03 (3H, d,
J = 6.9Hz).

Example 49 (56) N-hydroxy-2 (S) -methyl-5-methoxymethoxy-4 (S)-[N-[[5- (4-methoxyphenyl) -2-thienyl] carbonyl] Amino] pentanamide

Embedded image TLC: Rf 0.29 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.41 (s, 1H), 8.69 (s, 1H),
8.14 (d, J = 8.7Hz, 1H), 7.75 (d, J = 3.9Hz, 1H), 7.6
3 (d, J = 8.7Hz, 2H), 7.39 (d, J = 3.9Hz, 1H), 7.00 (d,
J = 8.7Hz, 2H), 4.57 (s, 2H), 4.20-4.00 (m, 1H), 3.
80 (s, 3H), 3.55-3.45 (m, 2H), 3.25 (s, 3H), 2.30-
2.15 (m, 1H), 1.68 (t, J = 7.2Hz, 2H), 1.04 (d, J = 6.
9Hz, 3H).

Example 49 (57) N-hydroxy-2 (S) -methyl-5-methoxymethoxy-4 (S)-[N- [4-[(biphenyl-3-yl) oxy] phenylcarbonyl] amino ] Pentanamide

Embedded image TLC: Rf 0.42 (chloroform: methanol: acetic acid = 100: 10: 1); NMR (d ₆ -DMSO): δ 10.38 (1H, s), 8.66 (1H, s),
8.06 (1H, d, J = 8.4Hz), 7.90 (2H, d, J = 8.4Hz), 7.68-7.
63 (2H, m), 7.52-7.33 (6H, m), 7.12-7.00 (3H, m), 4.55
(2H, s), 4.24-4.05 (1H, m), 3.54-3.40 (2H, m), 3.32
(3H, s), 2.15-2.25 (1H, m), 1.67 (2H, t, J = 7.0Hz),
1.01 (3H, d, J = 7.0Hz).

Example 49 (58) N-hydroxy-2 (S) -methyl-5-methoxymethoxy-4 (S)-[N- [4- (1-heptynyl) phenylcarbonyl] amino] pentanamide

Embedded image TLC: Rf 0.49 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.38 (1H, s), 8.66 (1H, s),
8.13 (1H, d, J = 8.8Hz), 7.82 (2H, d, J = 8.4Hz), 7.4
4 (2H, d, J = 8.4Hz), 4.56 (2H, s), 4.28-4.06 (1H,
m), 3.60-3.40 (2H, m), 3.23 (3H, s), 2.43 (2H, t,
J = 6.8Hz), 2.27-2.10 (1H, m), 1.74-1.46 (4H, m), 1.
45-1.20 (4H, m), 1.03 (3H, t, J = 6.6Hz), 0.90 (3H,
t, J = 7.0Hz).

Example 49 (59) N-hydroxy-2 (S) -methyl-5-methoxymethoxy-4 (S)-[N- [4- (3-phenoxy-1-
Propynyl) phenylcarbonyl] amino] pentanamide

Embedded image TLC: Rf 0.49 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.38 (1H, s), 8.66 (1H, s),
8.20 (1H, d, J = 8.7Hz), 7.85 (2H, d, J = 8.4Hz), 7.5
2 (2H, d, J = 8.4Hz), 7.37- 7.29 (2H, m), 7.08-6.96
(3H, m), 5.06 (2H, s), 4.55 (2H, s), 4.22-4.10 (1
H, m), 3.55-3.40 (2H, m), 3.22 (3H, s), 2.24-2.12
(1H, m), 1.67-1.58 (2H, m), 1.02 (3H, d, J = 6.9Hz).

Example 49 (60) N-hydroxy-2 (S) -methyl-5-methoxymethoxy-4 (S)-[N- [4- (4-cyanophenyl)
Phenylcarbonyl] amino] pentanamide

Embedded image TLC: Rf 0.34 (chloroform: methanol = 1
0: 1); NMR (d ₆ -DMSO): δ 10.40 (1H, d, J = 1.5 Hz), 8.67
(1H, d, J = 1.5Hz), 8.22 (1H, d, J = 8.7Hz), 7.98 (2
H, d, J = 8.4Hz), 7.95 (4H, s), 7.85 (2H, d, J = 8.4H
z), 4.56 (2H, s), 4.24-4.32 (1H, m), 3.55-3.45 (2
H, m), 3.23 (3H, s), 2.26-2.15 (1H, m), 1.77-1.62
(2H, m), 1.03 (3H, d, J = 6.9Hz).

Example 49 (61) N-hydroxy-2 (S) -methyl-5-methoxymethoxy-4 (S)-[N- [4- (3-cyanophenyl)
Phenylcarbonyl] amino] pentanamide

Embedded image TLC: Rf 0.35 (chloroform: methanol = 1
0: 1); NMR (d ₆ -DMSO): δ 10.40 (1H, d, J = 1.5 Hz), 8.67
(1H, d, J = 1.5Hz), 8.24 (1H, t, J = 1.5Hz), 8.21 (1
H, d, J = 8.7Hz), 8.10-8.07 (1H, m), 7.97 (2H, d, J =
8.4Hz), 7.88-7.84 (1H, m), 7.85 (2H, d, J = 8.4Hz),
7.69 (1H, t, J = 7.8Hz), 4.57 (2H, s), 4.24-4.13 (1
H, m), 3.55-3.45 (2H, m), 3.23 (3H, s), 2.26-2.15
(1H, m), 1.77-1.62 (2H, m), 1.03 (3H, d, J = 6.9H
z).

Example 49 (62) N-hydroxy-2 (S) -methyl-5-methoxymethoxy-4 (S)-[N- (4-benzylphenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.43 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.34 (1H, s), 8.64 (1H, s),
7.98 (1H, d, J = 8.4Hz), 7.74 (2H, d, J = 8.1Hz), 7.3
0-7.12 (7H, m), 4.52 (2H, s), 4.16-4.07 (1H, m),
3.96 (2H, s), 3.50-3.38 (2H, m), 3.19 (3H, s), 2.
19-2.09 (1H, m), 1.64 (2H, t, J = 7.4Hz), 0.98 (3H,
d, J = 6.6Hz).

Example 49 (63) N-hydroxy-2 (S) -methyl-5-methoxymethoxy-4 (S)-[N- [4- [2E- (pyridine-4)
-Yl) ethenyl] phenylcarbonyl] amino] pentanamide

Embedded image TLC: Rf 0.18 (chloroform: methanol: acetic acid = 100: 10: 1); NMR (d ₆ -DMSO): δ 10.42 (1H, s), 8.67 (1H, d, J =
1.5Hz), 8.56 (2H, d, J = 6.0Hz), 8.16 (1H, d, J = 8.4Hz),
7.89 (2H, d, J = 8.4Hz), 7.73 (2H, d, J = 8.4Hz), 7.59
(1H, d, J = 16.5Hz), 7.57 (2H, d, J = 6.0Hz), 7.36 (1H,
d, J = 16.5Hz), 4.56 (2H, s), 4.23-4.08 (1H, m), 3.54-
3.44 (2H, m), 3.22 (3H, s), 2.28-2.15 (1H, m), 1.72-
1.66 (2H, m), 1.02 (3H, d, J = 6.6Hz).

Example 49 (64) N-hydroxy-2 (S) -methyl-5-methoxymethoxy-4 (S)-[N- [4- (benzoxazole-
2-yl) phenylcarbonyl] amino] pentanamide

Embedded image TLC: Rf 0.28 (chloroform: methanol = 1
0: 1); NMR (d ₆ -DMSO): δ 10.41 (1H, brs), 8.68 (1H, b
rs), 8.35 (1H, d, J = 8.8Hz), 8.28 (2H, d, J = 8.4Hz),
8.07 (2H, d, J = 8.4Hz), 7.86-7.80 (2H, m), 7.51-7.3
8 (2H, m), 4.57 (2H, s), 4.28-4.11 (1H, m), 3.59-
3.42 (2H, m), 3.24 (3H, s), 2.30-2.13 (1H, m), 1.81
-1.59 (2H, m), 1.04 (3H, d, J = 6.6Hz).

Example 49 (65) N-hydroxy-2 (S) -methyl-5-methoxymethoxy-4 (S)-[N- [4- (3-ethoxyphenyl) phenylcarbonyl] amino] pentanamide

Embedded image TLC: Rf 0.35 (chloroform: methanol = 1
0: 1); NMR (d ₆ -DMSO): δ 10.39 (brs, 1H), 8.67 (brs,
1H), 8.16 (d, J = 8.4Hz, 1H), 7.93 (d, J = 8.12Hz,
2H), 7.75 (d, J = 8.1Hz, 2H), 7.38 (t, J = 8.1Hz,
1H), 7.26 (br.d, J = 8.1Hz, 1H), 7.22 (brs, 1H),
6.96 (dd, J = 8.1, 2.1Hz, 1H), 4.57 (s, 2H), 4.24-
4.13 (m, 1H), 4.10 (q, J = 7.2Hz, 2H), 3.55-3.45
(m, 2H), 3.23 (s, 3H), 2.26-2.14 (m, 1H), 1.77-1.6
2 (m, 2H), 1.35 (t, J = 7.2Hz, 3H), 1.03 (d, J =
6.6Hz, 3H).

Example 49 (66) N-hydroxy-2 (S) -methyl-5-methoxymethoxy-4 (S)-[N- [4- (4-methylphenylcarbonylamino) phenylcarbonyl] amino] pentane Amide

Embedded image TLC: Rf 0.22 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.38 (brs, 1H), 8.05 (d, J =
8.4Hz, 1H), 7.96-7.84 (m, 6H), 7.34 (d, J = 8.1Hz, 2
H), 4.57 (s, 2H), 4.25-4.10 (m, 1H), 3.60-3.40 (m,
2H), 3.25 (s, 3H), 2.40 (s, 3H), 2.30-2.15 (m, 1
H), 1.85-1.60 (m, 2H), 1.04 (d, J = 6.9Hz, 3H).

Example 49 (67) N-hydroxy-2 (S) -methyl-5-methoxymethoxy-4 (S)-[N-[[5- [2- (4-methylphenyl) ethynyl] -2 -Thienyl] carbonyl] amino] pentanamide

Embedded image TLC: Rf 0.27 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.41 (s, 1H), 8.69 (s, 1H),
8.31 (d, J = 8.7Hz, 1H), 7.77 (d, J = 4.1Hz, 1H), 7.
46 (d, J = 7.8Hz, 2H), 7.39 (d, J = 4.1Hz, 1H), 7.26
(d, J = 7.8Hz, 2H), 4.57 (s, 2H), 4.20-4.00 (m, 1H),
3.60-3.40 (m, 2H), 3.24 (s, 3H), 2.35 (s, 2H), 2.
20 (m, 1H), 1.68 (t, J = 7.2Hz, 2H), 1.03 (d, J = 6.9H
z, 3H).

Examples 49 (68) to 49 (92) The compounds prepared in Examples 44 (4) to 44 (6) and 44 (10) or the corresponding compounds in place of the compounds prepared in Reference Example 4 were used. Example 37 → Example 39 → Example 41 (using the corresponding compound in place of methoxymethyl chloride) → Example 43 (using methyl iodide instead of benzyl bromide) → Example 44 The compound obtained in the same manner as in the method shown above was operated in the same manner as in Example 49 to obtain the following compound.

Example 49 (68) N-hydroxy-2 (S) -methyl-5- (2-methoxyethoxy) methoxy-4 (S)-[N- (4-phenoxyphenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.43 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.35 (1H, s), 8.64 (1H, s),
8.01 (1H, d, J = 8.7Hz), 7.85 (2H, d, J = 8.7Hz), 7.4
1 (2H, t, J = 7.7Hz), 7.17 (1H, t, J = 7.7Hz), 7.04 (2
H, d, J = 7.7Hz), 7.00 (2H, d, J = 8.7Hz), 4.59 (2H,
s), 4.18-4.06 (1H, m), 3.55-3.37 (6H, m), 3.19 (3
H, s), 2.15 (1H, m), 1.68-1.60 (2H, m), 0.99 (3H,
d, J = 6.6Hz).

Example 49 (69 ) N-hydroxy-2 (S) -methyl-5-tert-butylcarbonyloxy-4 (S)-[N- (4-phenoxyphenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.52 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.38 (1H, s), 8.07 (1H, d,
J = 9.0Hz), 7.82 (2H, d, J = 8.7Hz), 7.41 (2H, t, J = 7.7
Hz), 7.18 (1H, t, J = 7.7Hz), 7.07-6.99 (4H, m), 4.3
0-4.18 (1H, m), 4.07-3.94 (2H, m), 2.20-2.1 1 (1H, m
m), 1.73-1.49 (2H, m), 1.06 (9H, s), 0.99 (3H, d,
J = 6.6Hz).

Example 49 (70) N-hydroxy-2 (S) -methyl-5-benzyloxymethoxy-4 (S)-[N- (4-phenoxyphenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.40 (chloroform: methanol: acetic acid: water = 100: 10: 1: 1); NMR (d ₆ -DMSO): δ 10.38 (s, 1H), 8.64 (s, 1H),
8.07 (d, J = 8.5Hz, 1H), 7.88 (d, J = 8.8Hz, 2H),
7.45-7.4 (m, 2H), 7.35-7.25 (m, 5H), 7.19 (t, J =
7.4Hz, 1H), 7.05 (d, J = 8.8Hz, 2H), 7.01 (d, J =
8.5Hz, 2H), 4.70 (s, 2H), 4.50 (s, 2H), 4.18 (m, 1
H), 3.58 (d, J = 11.3Hz, 1H), 3.53 (d, J = 11.3Hz,
1H), 2.19 (m, 1H), 1.30 (m, 2H), 1.01 (d, J = 6.9H
z, 3H).

Example 49 (71) N-hydroxy-2 (S) -methyl-5-ethoxymethoxy-4 (S)-[N- (trans-4-methylcyclohexylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.39 (chloroform: methanol = 1
0: 1); NMR (d ₆ -DMSO): δ 10.37 (brs, 1H), 8.66 (brs,
1H), 7.39 (d, J = 8.4Hz, 1H), 4.56 (s, 2H), 3.89-3.7
7 (m, 1H), 3.47 (q, J = 7.2Hz, 2H), 3.38-3.28 (m, 2
H), 2.14-1.92 (m, 2H), 1.74-1.59 (m, 4H), 1.56-1.4
6 (m, 2H), 1.40-1.21 (m, 3H), 1.10 (t, J = 7.2Hz, 3
H), 0.95 (d, J = 6.9Hz, 3H), 0.93-0.78 (m, 2H), 0.84
(d, J = 6.6Hz, 3H).

Example 49 (72) N-hydroxy-2 (S) -methyl-5-ethoxymethoxy-4 (S)-[N- (4-methylphenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.29 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.35 (s, 1H), 8.63 (brs, 1
H), 7.95 (d, J = 8.8Hz, 1H), 7.72 (d, J = 8.0Hz, 2H),
7.22 (d, J = 8.0Hz, 2H), 4.58 (s, 2H), 4.18-4.04 (m,
1H), 3.53-3.39 (m, 4H), 2.32 (s, 3H), 2.15 (m, 1
H), 1.64 (t, J = 7.4Hz, 2H), 1.06 (t, J = 7.1Hz, 3H),
0.99 (d, J = 7.0Hz, 3H).

Example 49 (73) N-hydroxy-2 (S) -methyl-5-ethoxymethoxy-4 (S)-[N- (4-chlorophenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.44 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.36 (s, 1H), 8.15 (d, J =
8.4Hz, 1H), 7.83 (d, J = 8.8Hz, 2H), 7.50 (d, J =
8.8Hz, 2H), 4.57 (s, 2H), 4.21-4.06 (m, 1H), 3.53-
3.38 (m, 4H), 2.22-2.10 (m, 1H), 1.64 (t, J = 7.0H
z, 2H), 1.06 (t, J = 6.9Hz, 3H), 0.99 (d, J = 6.6H
z, 3H).

Example 49 (74) N-hydroxy-2 (S) -methyl-5-ethoxymethoxy-4 (S)-[N- (adamantylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.46 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.35 (s, 1H), 8.63 (s, 1H),
6.80 (d, J = 9.0Hz, 1H), 4.54 (s, 2H), 3.94-3.83
(m, 1H), 3.43 (q, J = 7.2Hz, 2H), 3.36-3.24 (m, 2
H), 2.14-2.02 (m, 1H), 1.96-1.88 (m, 3H), 1.76-1.4
5 (m, 14H), 1.09 (t, J = 7.2Hz, 3H), 0.92 (d, J =
6.6Hz, 3H).

Example 49 (75 ) N-hydroxy-2 (S) -methyl-5-ethoxymethoxy-4 (S)-[N- (2-furylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.24 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.34 (s, 1H), 8.63 (s, 1H),
7.96 (d, J = 8.4Hz, 1H), 7.80-7.79 (m, 1H), 7.06
(d, J = 3.4Hz, 1H), 6.58 (dd, J = 3.4Hz, 1.7Hz, 1
H), 4.56 (s, 2H), 4.15-4.02 (m, 1H), 3.51-3.38 (m,
4H), 2.18-2.04 (m, 1H), 1.61 (t, J = 6.2Hz, 2H), 1.0
6 (t, J = 7.1 Hz, 3H), 0.97 (d, J = 6.8 Hz, 3H).

Example 49 (76) N-hydroxy-2 (S) -methyl-5-ethoxymethoxy-4 (S)-[N-[(benzothiazol-6-yl) carbonyl] amino] pentanamide

Embedded image TLC: Rf 0.34 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.37 (s, 1H), 9.50 (s, 1H),
8.62 (d, J = 1.5 Hz, 1H), 8.23 (d, J = 8.4 Hz, 1
H), 8.12 (d, J = 8.7Hz, 1H), 7.97 (dd, J = 8.7Hz,
1.9Hz, 1H), 4.59 (s, 2H), 4.21-4.11 (m, 1H), 3.5 3
-3.42 (m, 4H), 2.25-2.14 (m, 1H), 1.72-1.61 (m, 2
H), 1.06 (t, J = 7.2Hz, 3H), 1.00 (d, J = 6.6Hz, 3
H).

Example 49 (77) N-hydroxy-2 (S) -methyl-5-ethoxymethoxy-4 (S)-[N- (4-fluorophenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.34 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.36 (s, 1H), 8.09 (d, J =
8.7Hz, 1H), 7.88 (dd, J = 5.7Hz, 9.0Hz, 2H), 7.26
(t, J = 9.0 Hz, 2H), 4.57 (s, 2H), 4.16-4.05 (m, 1
H), 3.50-3.41 (m, 4H), 2.15 (m, 1H), 1.68-1.61 (m,
2H), 1.06 (t, J = 7.0Hz, 3H), 0.98 (d, J = 6.8Hz, 3
H).

Example 49 (78) N-hydroxy-2 (S) -methyl-5-ethoxymethoxy-4 (S)-[N-[(2-bromofuryl-5-yl) carbonyl] amino] pentanamide

Embedded image TLC: Rf 0.28 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.35 (s, 1H), 9.64 (s, 1H),
8.07 (d, J = 8.7Hz, 1H), 7.10 (d, J = 3.6Hz, 1H),
6.72 (d, J = 3.6Hz, 1H), 4.56 (s, 2H), 4.11-4.00
(m, 1H), 3.49-3.40 (m, 4H), 2.16-2.05 (m, 1H), 1.6
7-1.53 (m, 2H), 1.06 (t, J = 7.2Hz, 3H), 0.97 (d, J
= 6.3Hz, 3H).

Example 49 (79) N-hydroxy-2 (S) -methyl-5-ethoxymethoxy-4 (S)-[N- (4-nitrophenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.35 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.39 (brs, 1H), 8.66 (brs,
1H), 8.46 (brd, J = 8.8Hz, 1H), 8.30 (d, J = 8.8Hz,
1H), 8.06 (d, J = 8.8Hz, 2H), 4.59 (s, 2H), 4.15
(m, 1H), 3.50 (d, J = 5.8Hz, 1H), 3.47 (q, J = 6.8
Hz, 2H), 2.17 (m, 1H), 1.67 (m, 2H), 1.07 (t, J =
6.8Hz, 3H), 1.02 (d, J = 6.8Hz, 3H).

Example 49 (80) N-hydroxy-2 (S) -methyl-5-ethoxymethoxy-4 (S)-[N- (4-bromophenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.35 (methylene chloride: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.37 (brs, 1H), 8.65 (brs,
1H), 8.17 (brd, J = 8.4Hz, 1H), 7.79 (d, J = 8.8Hz,
2H), 7.66 (d, J = 8.8Hz, 2H), 4.58 (s, 2H), 4.13
(m, 1H), 3.47 (d, J = 7.0Hz, 2H), 3.47 (q, J = 7.0
Hz, 2H), 2.16 (m, 1H), 1.65 (m, 2H), 1.07 (t, J =
7.0Hz, 3H), 1.01 (d, J = 6.6Hz, 3H).

Example 49 (81) N-hydroxy-2 (S) -methyl-5-ethoxymethoxy-4 (S)-[N- (4-cyanophenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.24 (chloroform: methanol = 1
9: 1); NMR (d ₆ -DMSO): δ 10.39 (s, 1H), 8.67 (s, 1H),
8.36 (d, J = 8.7Hz, 1H), 8.00 (d, J = 8.4Hz, 2H),
7.95 (d, J = 8.4Hz, 2H), 4.60 (s, 2H), 4.22-4.08
(m, 1H), 3.58-3.40 (m, 4H), 2.23-2.12 (m, 1H), 1.78
-1.58 (m, 2H), 1.09 (t, J = 6.9Hz, 3H), 1.03 (d, J
= 6.9Hz, 3H).

Example 49 (82) N-hydroxy-2 (S) -methyl-5-ethoxymethoxy-4 (S)-[N- [4- (4-pyridyloxy)
Phenylcarbonyl] amino] pentanamide

Embedded image TLC: Rf 0.30 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.40 (s, 1H), 8.69 (s, 1H),
8.50 (dd, J = 4.7,1.5Hz, 2H), 8.15 (d, J = 8.4Hz,
1H), 7.98 (d, J = 8.7Hz, 2H), 7.25 (d, J = 8.7Hz,
2H), 6.97 (dd, J = 4.7, 1.5Hz, 2H), 4.62 (s, 2H),
4.30-4.10 (m, 1H), 3.60-3.40 (m, 4H), 2.30-2.10
(m, 1H), 1.80-1.60 (m, 2H), 1.11 (t, J = 7.1Hz, 3
H), 1.04 (d, J = 6.9 Hz, 3H).

Example 49 (83) N-hydroxy-2 (S) -methyl-5- (2-methoxyethoxy) methoxy-4 (S)-[N- (4-cyanophenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.26 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.37 (s, 1H), 8.65 (s, 1H),
8.36 (d, J = 8.7Hz, 1H), 8.00-7.93 (m, 4H), 4.61
(s, 2H), 4.20-4.06 (m, 1H), 3.56-3.52 (m, 2H), 3.49
(d, J = 6.0Hz, 2H), 3.42-3.39 (m, 2H), 3.20 (s, 3
H), 2.20-2.12 (m, 1H), 1.75-1.58 (m, 2H), 1.01 (t,
J = 6.9Hz, 3H).

Example 49 (84) N-hydroxy-2 (S) -methyl-5-methoxymethoxy-4 (S)-[N- (4-chlorophenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.50 (methylene chloride: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.36 (d, J = 1.8 Hz, 1H), 8.
64 (d, J = 1.8Hz, 1H), 8.17 (d, J = 8.4Hz, 1H), 7.
85 (d, J = 8.4Hz, 2H), 7.51 (d, J = 8.4Hz, 2H), 4.5
3 (s, 2H), 4.11 (m, 1H), 3.46 (m, 2H), 3.20 (s, 3
H), 2.16 (m, 1H), 1.65 (m, 2H), 1.00 (d, J = 6.6H
z, 3H).

Example 49 (85) N-hydroxy-2 (S) -methyl-5-benzyloxymethoxy-4 (S)-[N- (4-chlorophenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.50 (methylene chloride: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.36 (s, 1H), 8.64 (s, 1H),
8.19 (d, J = 8.4Hz, 1H), 7.86 (d, J = 9.0Hz, 2H),
7.51 (d, J = 9.0Hz, 2H), 7.28 (m, 5H), 4.69 (s, 2
H), 4.49 (s, 2H), 4.15 (m, 1H), 3.54 (d, J = 6.0H
z, 2H), 2.17 (m, 1H), 1.68 (m, 2H), 1.00 (d, J =
6.9Hz, 3H).

Example 49 (86) N-hydroxy-2 (S) -methyl-5- (2-methoxyethoxy) methoxy-4 (S)-[N- (4-chlorophenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.45 (methylene chloride: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.36 (s, 1H), 8.64 (s, 1H),
8.16 (d, J = 8.4Hz, 1H), 7.85 (d, J = 9.0Hz, 2H),
7.51 (d, J = 9.0Hz, 2H), 4.60 (s, 2H), 4.13 (m, 1
H), 3.55-3.38 (m, 6H), 3.19 (s, 3H), 2.14 (m, 1H),
1.65 (m, 2H), 1.00 (d, J = 6.9Hz, 3H).

Example 49 (87) N-hydroxy-2 (S) -methyl-5-ethoxymethoxy-4 (S)-[N- (2-nitrophenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.22 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.39 (d, J = 1.2 Hz, 1H), 8.70
(d, J = 1.2Hz, 1H), 8.45 (d, J = 8.4Hz, 1H), 8.01 (d
d, J = 7.8Hz, 1.2Hz, 1H), 7.80-7.60 (m, 3H), 4.62 (s,
2H), 4.08-3.95 (m, 1H), 3.55-3.36 (m, 4H), 2.31-
2.19 (m, 1H), 1.65 (t, J = 7.2Hz, 2H), 1.12 (t, J = 7.
2Hz, 3H), 1.03 (d, J = 7.2Hz, 3H).

Example 49 (88) N-hydroxy-2 (S) -methyl-5-ethoxymethoxy-4 (S)-[N- (3-nitrophenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.31 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.38 (s, 1H), 8.69-8.68 (m,
1H), 8.64 (brs, 1H), 8.52 (d, J = 8.7Hz, 1H), 8.3
9-8.35 (m, 1H), 8.30-8.27 (m, 1H), 7.77 (t, J = 8.
1Hz, 1H), 4.60 (s, 2H), 4.24-4.11 (m, 1H), 3.52-3.
44 (m, 4H), 2.22-2.11 (m, 1H), 1.78-1.60 (m, 2H),
1.08 (t, J = 7.2 Hz, 3H), 1.02 (d, J = 6.9 Hz, 3H).

Example 49 (89) N-hydroxy-2 (S) -methyl-5-ethoxymethoxy-4 (S)-[N- (2-methoxy-4-nitrophenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.26 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.38 (s, 1H), 8.66 (brs, 1
H), 8.09 (d, J = 8.4Hz, 1H), 7.87-7.77 (m, 3H), 4.
61, (s, 2H), 4.14-4.02 (m, 1H), 3.95 (s, 3H), 3.53
-3.43 (m, 4H), 2.25-2.13 (m, 1H), 1.75-1.55 (m, 2
H), 1.09 (t, J = 6.9Hz, 3H), 1.02 (d, J = 6.9Hz, 3
H).

Example 49 (90) N-hydroxy-2 (S) -methyl-5-ethoxymethoxy-4 (S)-[N- (3-methoxy-4-nitrophenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.26 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.39 (s, 1H), 8.67 (s, 1H),
8.34 (d, J = 8.4Hz, 1H), 7.94 (d, J = 8.7Hz, 1H),
7.70 (d, J = 1.2Hz, 1H), 7.53 (dd, J = 8.7Hz, 1.2H
z, 1H), 4.60 (s, 2H), 4.21-4.09 (m, 1H), 3.99 (s,
3H), 3.54-3.45 (m, 4H), 2.22-2.10 (m, 1H), 1.78-1.
62 (m, 2H), 1.08 (t, J = 6.9Hz, 3H), 1.02 (d, J =
6.9Hz, 3H).

Example 49 (91) N-hydroxy-2 (S) -methyl-5-ethoxymethoxy-4 (S)-[N- (3-hydroxy-4-nitrophenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.22 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 11.08 (s, 1H), 10.28 (s, 1)
H), 8.56 (s, 1H), 8.21 (d, J = 8.7Hz, 1H), 7.84 (d,
J = 8.4Hz, 1H), 7.43 (d, J = 1.8Hz, 1H), 7.28 (d
d, J = 8.4Hz, 1.8Hz, 1H), 4.49 (s, 2H), 4.08-3.95
(m, 1H), 3.41-3.34 (m, 4H), 2.12-2.01 (m, 1H), 1.5
8-1.53 (m, 2H), 0.99 (t, J = 6.9Hz, 3H), 0.91 (d,
J = 6.9Hz, 3H).

Example 49 (92) N-hydroxy-2 (S) -methyl-5-ethoxymethoxy-4 (S)-[N- (4-dihydroxyboronylphenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.19 (methylene chloride: methanol: acetic acid = 18: 1: 1); NMR (d ₆ -DMSO): δ 10.37 (s, 1H), 8.65 (s, 1H),
8.16 (s, 2H), 8.05 (d, J = 8.4Hz, 1H), 7.83 (d, J
= 8.4Hz, 2H), 7.77 (d, J = 8.4Hz, 2H), 4.58 (s, 2
H), 4.14 (m, 1H), 3.47 (m, 4H), 2.16 (m, 1H), 1.66
(m, 2H), 1.07 (t, J = 6.9Hz, 3H), 1.01 (d, J = 6.9
Hz, 3H).

Embodiments 49 (93) to 49 (111) Embodiments 44 (7), 44 (12), 44 (13), 44
(15), 44 (16), 44 (22), 44 (2
Example 37 → Example 3 using the corresponding compound in place of the compound prepared in 3), 44 (27) or Reference Example 4
9 → Example 41 (A corresponding compound may be used in place of methoxymethyl chloride.) → Example 43
(Use the corresponding compound in place of benzyl bromide.)
→ A compound obtained by operating in the same manner as in the method shown in Example 44,
The following compounds were obtained.

Example 49 (93) N-hydroxy-2 (S) -isobutyl-5-methoxymethoxy-4 (S)-[N- (4-phenoxyphenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.36 (chloroform: methanol = 1
9: 1); NMR (d ₆ -DMSO): δ 10.46 (1H, s), 8.72 (1H, s),
8.00 (1H, d, J = 8.4Hz), 7.88 (2H, d, J = 8.8Hz), 7.4
8-7.38 (2H, m), 7.23-7.16 (1H, m), 7.10-7.03 (2H, m
m), 7.01 (2H, d, J = 8.8Hz), 4.56 (2H, s), 4.22-4.0
1 (1H, m), 3.60-3.40 (2H, m), 3.24 (3H, s), 2.25-
2.08 (1H, m), 1.78-1.60 (2H, m), 1.58-1.32 (2H,
m), 1.28-1.07 (1H, m), 0.82 (3H, d, J = 6.0Hz), 0.80
(3H, d, J = 6.0Hz).

Example 49 (94) N-hydroxy-2 (S) -ethyl-5-methoxymethoxy-4 (S)-[N- (4-phenoxyphenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.60 (chloroform: methanol: acetic acid: water = 100: 10: 1: 1); NMR (d ₆ -DMSO): δ 10.40 (1H, s), 8.71 (1H, s),
8.04 (1H, d, J = 8.1Hz), 7.87 (2H, d, J = 9.0Hz), 7.45-7.
40 (2H, m), 7.22-7.17 (1H, m), 7.08-7.00 (4H, m), 4.55
(2H, s), 4.04-4.18 (1H, m), 3.52-3.23 (2H, m), 3.22
(3H, s), 2.04-1.92 (1H, m), 1.78-1.57 (2H, m), 1.52-
1.34 (2H, m), 0.77 (3H, t, J = 7.2Hz).

Example 49 (95) N-hydroxy-2 (S) -propyl-5-methoxymethoxy-4 (S)-[N- (4-phenoxyphenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.60 (chloroform: methanol: acetic acid: water = 100: 10: 1: 1); NMR (d ₆ -DMSO): δ 10.40 (1H, s), 8.69 (1H, s),
8.02 (1H, d, J = 8.4Hz), 7.86 (2H, d, J = 8.8Hz), 7.46-7.
37 (2H, m), 7.23-7.15 (1H, m), 7.08-6.98 (4H, m), 4.54
(2H, s), 4.16-4.00 (1H, m), 3.48-3.44 (2H, m), 3.21
(3H, s), 2.14-1.99 (1H, m), 1.78-1.58 (2H, m), 1.45-
1.28 (2H, m), 1.27-1.07 (2H, m), 0.80 (3H, t, J = 7.2H
z).

Example 49 (96) N-hydroxy-2 (R) -tert-butoxycarbonylmethyl-5-methoxymethoxy-4 (S)-[N- (4-
Phenoxyphenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.54 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.47 (1H, s), 8.75 (1H, s),
8.05 (1H, d, J = 8.4Hz), 7.88 (2H, d, J = 8.7Hz), 7.4
7-7.40 (2H, m), 7.23-7.17 (1H, m), 7.10-7.04 (2H, m
m), 7.03 (2H, d, J = 8.7Hz), 4.55 (2H, s), 4.20-4.03
(1H, m), 3.57-3.43 (2H, m), 3.23 (3H, s), 2.55-2.
34 (3H, m), 1.74-1.66 (2H, m), 1.36 (9H, s).

Example 49 (97) N-hydroxy-2 (S) -allyl-5-methoxymethoxy-4 (S)-[N- (4-phenoxyphenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.62 (chloroform: methanol: acetic acid = 100: 5: 1); NMR (d ₆ -DMSO): δ 10.43 (1H, s), 8.66 (1H, brs),
8.06 (1H, d, J = 8.4Hz), 7.89-7.85 (2H, m), 7.47-7.38
(2H, m), 7.23-7.15 (1H, m), 7.09-6.99 (4H, m), 5.73-
5.60 (1H, m), 5.05-4.92 (2H, m), 4.54 (2H, s), 4.19-
4.05 (1H, m), 3.52 (1H, dd, J = 10.1Hz, 5.2Hz), 3.44 (1
H, dd, J = 10.1Hz, 5.2Hz), 3.22 (3H, s), 2.20-2.17 (3H,
m), 1.82-1.59 (2H, m).

Example 49 (98 ) N-hydroxy-2 (S) -ethyl-5-ethoxymethoxy-4 (S)-[N- (4-phenoxyphenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.33 (chloroform: methanol: acetic acid = 100: 5: 1); NMR (d ₆ -DMSO): δ 10.40 (1H, s), 8.70 (1H, s),
8.02 (1H, d, J = 8.4Hz), 7.86 (2H, d, J = 8.8Hz), 7.46-7.
38 (2H, m), 7.23-7.15 (1H, m), 7.08-6.99 (4H, m), 4.59
(2H, s), 4.19-4.01 (1H, m), 3.52-3.42 (2H, m), 3.47
(2H, q, J = 7.0Hz), 2.05-1.92 (1H, m), 1.79-1.32 (4H,
m), 1.07 (3H, t, J = 7.2Hz), 0.76 (3H, t, J = 7.0Hz).

Example 49 (99) N-hydroxy-2 (S) -ethyl-5- (2-methoxyethoxy) methoxy-4 (S)-[N- (4-phenoxyphenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.31 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.40 (1H, s), 8.71 (1H, s),
8.02 (1H, d, J = 8.4Hz), 7.88 (2H, d, J = 8.8Hz), 7.4
8-7.38 (2H, m), 7.23-7.15 (1H, m), 7.10-7.05 (2H, m
m), 7.02 (2H, d, J = 8.8Hz), 4.62 (2H, m), 4.22-4.00
(1H, m), 3.61-3.38 (6H, m), 3.22 (3H, s), 2.09-1.
91 (1H, m), 1.82-1.60 (2H, m), 1.58-1.35 (2H, m),
0.78 (3H, t, J = 7.0Hz).

Example 49 (100 ) N-hydroxy-2 (S) -ethyl-5-tert-butylcarbonyloxy-4 (S)-[N- (4-phenoxyphenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.69 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.41 (1H, s), 8.71 (1H, s),
8.07 (1H, d, J = 8.7Hz), 7.81 (2H, d, J = 8.6Hz), 7.4
1 (2H, t, J = 7.6Hz), 7.17 (1H, t, J = 7.6Hz), 7.04 (2
H, d, J = 7.6Hz), 7.00 (2H, d, J = 8.6Hz), 4.25-4.13
(1H, m), 4.08-3.94 (2H, m), 2.03-1.91 (1H, m), 1.6
3 (2H, t, J = 6.9Hz), 1.48-1.36 (2H, m), 1.06 (9H,
s), 0.75 (3H, t, J = 7.5Hz).

Example 49 (101) N-hydroxy-2 (S) -allyl-5-ethoxymethoxy-4 (S)-[N- (4-methylphenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.49 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.42 (s, 1H), 8.71 (s, 1H),
7.99 (d, J = 8.8Hz, 1H), 7.73 (d, J = 8.0Hz, 2H),
7.24 (d, J = 8.0Hz, 2H), 5.72-5.55 (m, 1H), 5.02-
4.91 (m, 2H), 4.58 (s, 2H), 4.19-4.01 (m, 1H), 3.5
2-3.41 (m, 4H), 2.33 (s, 3H), 2.12 (m, 3H), 1.79-
1.58 (m, 2H), 1.07 (t, J = 7.0Hz, 3H).

Example 49 (102) N-hydroxy-2 (S) -allyl-5-ethoxymethoxy-4 (S)-[N- (4-nitrophenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.32 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.43 (d, J = 1.5 Hz, 1H), 8.
71 (d, J = 1.5Hz, 1H), 8.47 (d, J = 8.4Hz, 1H), 8.
30-8.27 (m, 2H), 8.07-8.03 (m, 2H), 5.75-5.59 (m,
1H), 5.03-4.93 (m, 2H), 4.59 (s, 2H), 4.19-4.08
(m, 1H), 3.50 (d, J = 5.1Hz, 2H), 3.47 (q, J = 7.2
Hz, 2H), 2.23-2.12 (m, 3H), 1.80-1.60 (m, 2H), 1.07
(t, J = 7.2Hz, 3H).

Example 49 (103) N-hydroxy-2-methylidene-5-ethoxymethoxy-4 (S)-[N- (4-nitrophenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.50 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.77 (s, 1H), 8.84 (s, 1H),
8.61 (d, J = 8.4Hz, 1H), 8.32-8.27 (m, 2H), 8.05-
8.02 (m, 2H), 5.57 (s, 1H), 5.36 (s, 1H), 4.60 (s,
2H), 4.30-4.18 (m, 1H), 3.53-3.45 (m, 4H), 2.61 (d
d, J = 14.1Hz, 4.5Hz, 1H), 2.47-2.40 (m, 1H), 1.0
7 (t, J = 6.9 Hz, 3H).

Example 49 (104) N-hydroxy-2 (S)-(2-propynyl) -5
Ethoxymethoxy-4 (S)-[N- (4-nitrophenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.39 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.54 (s, 1H), 8.81 (s, 1H),
8.49 (d, J = 8.4Hz, 1H), 8.29 (d, J = 8.7Hz, 2H),
8.07 (d, J = 8.7Hz, 2H), 4.59 (s, 2H), 4.20-4.03
(m, 1H), 3.60-3.40 (m, 4H), 2.78 (s, 1H), 2.40-2.2
0 (m, 3H), 1.95-1.80 (m, 1H), 1.80-1.60 (m, 1H),
1.08 (t, J = 7.1 Hz, 3H).

Example 49 (105) N-hydroxy-2 (S) -allyl-5- (2-methoxyethoxy) methoxy-4 (S)-[N- (4-cyanophenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.22 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.42 (s, 1H), 8.71 (s, 1H),
8.36 (d, J = 8.7Hz, 1H), 7.98 (d, J = 8.4Hz, 2H),
7.94 (d, J = 8.4Hz, 2H), 5.74-5.58 (m, 1H), 5.05-
4.92 (m, 2H), 4.61 (s, 2H), 4.20-4.04 (m, 1H), 3.5
8-3.43 (m, 4H), 3.44- 3.37 (m, 2H), 3.19 (s, 3H),
2.22-2.10 (m, 3H), 1.81-1.58 (m, 2H).

Example 49 (106) N-hydroxy-2 (S)-(2-propynyl) -5
Ethoxymethoxy-4 (S)-[N- (4-bromophenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.36 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.52 (s, 1H), 8.80 (s, 1H),
8.20 (d, J = 8.7Hz, 1H), 7.79 (d, J = 8.4Hz, 2H), 7.6
4 (d, J = 8.4Hz, 2H), 4.58 (s, 2H), 4.18-4.02 (m, 1
H), 3.58-3.42 (m, 4H), 2.78-2.73 (brs, 1H), 2.38-
2.20 (m, 3H), 1.95-1.75 (m, 1H), 1.75-1.60 (m, 1
H), 1.08 (t, J = 6.9Hz, 3H).

Example 49 (107) N-hydroxy-2 (S)-(2-propynyl) -5
Ethoxymethoxy-4 (S)-[N- (4-chlorophenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.35 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.52 (s, 1H), 8.80 (s, 1H),
8.20 (d, J = 8.7Hz, 1H), 7.86 (d, J = 8.6Hz, 2H), 7.5
1 (d, J = 8.6Hz, 2H), 4.58 (s, 2H), 4.20-4.02 (m, 1
H), 3.60-3.40 (m, 4H), 2.80-2.75 (brs, 1H), 2.40-
2.20 (m, 3H), 1.95-1.78 (m, 1H), 1.78-1.60 (m, 1
H), 1.08 (t, J = 6.9Hz, 3H).

Example 49 (108) N-hydroxy-2 (S) -allyl-5-ethoxymethoxy-4 (S)-[N- (4-bromophenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.35 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.42 (s, 1H), 8.71 (s, 1H),
8.19 (d, J = 8.7Hz, 1H), 7.78 (d, J = 8.6Hz, 2H), 7.6
5 (d, J = 8.6Hz, 2H), 5.75-5.58 (m, 1H), 5.05-4.90
(m, 2H), 4.58 (s, 2H), 4.20-4.05 (m, 1H), 3.58-3.4
0 (m, 4H), 2.25-2.08 (m, 3H), 1.80-1.60 (m, 2H),
1.07 (t, J = 7.1Hz, 3H).

Example 49 (109) N-hydroxy-2 (S) -allyl-5-ethoxymethoxy-4 (S)-[N- (4-chlorophenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.36 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.42 (s, 1H), 8.70 (s, 1H),
8.18 (d, J = 8.7Hz, 1H), 7.85 (d, J = 8.6Hz, 2H), 7.5
2 (d, J = 8.6Hz, 2H), 5.75-5.58 (m, 1H), 5.05-4.90
(m, 2H), 4.58 (s, 2H), 4.20-4.05 (m, 1H), 3.58-3.4
0 (m, 4H), 2.25-2.08 (m, 3H), 1.80-1.60 (m, 2H),
1.07 (t, J = 7.1Hz, 3H).

Example 49 (110) N-hydroxy-2 (R) -dimethylaminomethyl-5
-Ethoxymethoxy-4 (S)-[N- (4-nitrophenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.30 (chloroform: methanol: acetic acid = 10: 2: 1); NMR (d ₆ -DMSO): δ 10.44 (brs, 1H), 8.73 (brs,
1H), 8.48 (d, J = 8.4Hz, 1H), 8.29 (d, J = 8.9Hz, 2H),
8.05 (d, J = 8.9Hz, 2H), 4.59 (s, 2H), 4.20-4.05
(m, 1H), 3.60-3.40 (m, 4H), 2.55-2.38 (m, 1H), 2.3
8-2.20 (m, 1H), 2.20-2.00 (m, 7H), 1.85-1.70 (m, 1
H), 1.70-1.58 (m, 1H), 1.08 (t, J = 6.9Hz, 3H).

Example 49 (111) N-Hydroxy-2 (S)-(2-propynyl) -5
(2-methoxyethoxy) methoxy-4 (S)-[N-
(4-cyanophenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.35 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.53 (s, 1H), 8.81 (s, 1H),
8.41 (d, J = 8.7Hz, 1H), 7.99 (d, J = 8.7Hz, 2H), 7.9
4 (d, J = 8.7Hz, 2H), 4.61 (s, 2H), 4.20-4.05 (m, 1
H), 3.60-3.45 (m, 4H), 3.45-3.35 (m, 2H), 3.20 (s,
3H), 2.79 (s, 1H), 2.35-2.00 (m, 3H), 1.92-1.75
(m, 1H), 1.75-1.60 (m, 1H).

Examples 49 (112) -49 (116) In place of 4 (S) -carboxy-4-aminobutanoic acid methyl ester, 4 (R) -carboxy-4-aminobutanoic acid methyl ester and Reference Example 4 Example 37 → Example 39 → Example 41 using a corresponding compound instead of the produced compound (In some cases, a corresponding compound may be used instead of methoxymethyl chloride) → Example 4.
3 (using the corresponding compound in place of benzyl bromide) → Example 44 → The same procedure as shown in Example 49 was performed to obtain the compound shown below.

Example 49 (112) N-hydroxy-2 (R) -benzyl-5-methoxymethoxy-4 (R)-[N- (4-phenoxyphenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.39 (chloroform: methanol: acetic acid: water = 100: 10: 1: 1); NMR (d ₆ -DMSO): δ 10.34 (1H, s), 8.66 (1H, s),
8.08 (1H, d, J = 8.8Hz), 7.89 (2H, d, J = 8.4Hz), 7.43 (2
(H, t, J = 8.0Hz), 7.00-7.46 (10H, m), 4.53 (2H, s), 4.1
3-4.32 (1H, m), 3.48 (2H, d, J = 5.6Hz), 3.19 (3H, s),
2.76 (2H, d, J = 7.0Hz), 2.29-2.44 (1H, m), 1.58-1.84
(2H, m).

Example 49 (113) N-hydroxy-2 (R) -benzyl-5-methoxymethoxy-4 (R)-[N- [4- (3-phenoxy-1)
-Propynyl) phenylcarbonyl] amino] pentanamide

Embedded image TLC: Rf 0.39 (chloroform: methanol: acetic acid: water = 100: 10: 1: 1); NMR (d ₆ -DMSO): δ 10.33 (1H, s), 8.65 (1H, s),
8.22 (1H, d, J = 8.7Hz), 7.84 (2H, d, J = 8.4Hz), 7.51 (2
H, d, J = 8.4Hz), 7.32 (2H, t, J = 7.8Hz), 7.20 (2H, t,
J = 6.9Hz), 6.97-7.14 (6H, m), 5.05 (2H, s), 4.50 (2H,
s), 4.14-4.28 (1H, m), 3.46 (2H, d, J = 5.7Hz), 3.17 (3
H, s), 2.74 (2H, d, J = 7.2Hz), 2.29-2.39 (1H, m), 1.6
0-1.79 (2H, m).

Example 49 (114) N-hydroxy-2 (R) -methyl-5-ethoxymethoxy-4 (R)-[N- [4- (4-cyanophenyl)
Phenylcarbonyl] amino] pentanamide

Embedded image TLC: Rf 0.35 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.37 (s, 1H), 8.65 (s, 1H),
8.18 (d, J = 8.4Hz, 1H), 7.95 (d, J = 8.6Hz, 2H), 7.8
3 (d, J = 8.6Hz, 2H), 4.59 (s, 2H), 4.16 (m, 1H), 3.6
0-3.40 (m, 4H), 2.17 (m, 1H), 1.67 (t, J = 6.9Hz, 2
H), 1.07 (t, J = 7.1 Hz, 3H), 1.01 (d, J = 6.9 Hz, 3H).

Example 49 (115) N-hydroxy-2 (R) -allyl-5-ethoxymethoxy-4 (R)-[N- (4-phenoxyphenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.34 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.41 (s, 1H), 8.70 (s, 1H),
8.02 (d, J = 8.4Hz, 1H), 7.85 (d, J = 9.0Hz, 2H), 7.4
1 (t, J = 7.9Hz, 2H), 7.17 (t, J = 7.9Hz, 1H), 7.04 (d,
J = 7.9Hz, 2H), 6.99 (d, J = 9.0Hz, 2H), 5.74- 5.55
(m, 1H), 5.03-4.88 (m, 2H), 4.56 (s, 2H), 4.17-4.0
3 (m, 1H), 3.53-3.40 (m, 4H), 2.24-2.10 (m, 3H),
1.79-1.58 (m, 2H), 1.06 (t, J = 7.0Hz, 3H).

Example 49 (116) N-hydroxy-2 (R) -methyl-5-ethoxymethoxy-4 (R)-[N- (4-phenoxyphenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.38 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.36 (s, 1H), 8.64 (s, 1H),
8.01 (d, J = 8.7Hz, 1H), 7.85 (d, J = 8.7Hz, 2H), 7.4
1 (t, J = 7.6Hz, 2H), 7.17 (t, J = 7.6Hz, 1H), 7.04 (d,
J = 7.6Hz, 2H), 7.00 (d, J = 8.7Hz, 2H), 4.57 (s, 2
H), 4.18-4.06 (m, 1H), 3.51-3.42 (m, 4H), 2.15 (m,
1H), 1.64 (t, J = 7.1Hz, 2H), 1.06 (t, J = 7.2Hz, 3H),
0.99 (d, J = 7.1Hz, 3H).

Examples 49 (117) to 49 (124) Example 37 → Example 39 → Example 41 → Example 4 using the corresponding compound in place of the compound prepared in Reference Example 4.
3 (using the corresponding compound in place of benzyl bromide) → Example 44 → The same procedure as shown in Example 49 was performed to obtain the compound shown below.

Example 49 (117) N-hydroxy-2 (S) -benzyl-5-methoxymethoxy-4 (S)-[N- [4- [2E- (4-chlorophenyl) ethenyl] phenylcarbonyl] amino ] Pentanamide

Embedded image TLC: Rf 0.21 (chloroform: methanol = 1
9: 1); NMR (d ₆ -DMSO): δ 10.37 (1H, s), 8.15 (1H, d,
J = 8.4Hz), 7.89 (2H, d, J = 8.4Hz), 7.68 (2H, d, J = 8.4
Hz), 7.66 (2H, d, J = 8.8Hz), 7.45 (2H, d, J = 8.8Hz),
7.40-7.30 (2H, m), 7.29-7.08 (5H, m), 4.54 (2H, m
s), 4.38-4.18 (1H, m), 3.60-3.40 (2H, m), 3.21 (3H,
s), 2.78 (2H, d, J = 6.6Hz), 2.55-2.30 (1H, m), 1.
92-1.60 (2H, m).

Example 49 (118) N-hydroxy-2 (S)-(indol-3-yl)
-5-methoxymethoxy-4 (S)-[N- [4- (benzofuran-2-yl) phenylcarbonyl] amino]
Pentanamide

Embedded image TLC: Rf 0.28 (chloroform: methanol = 1
9: 1); NMR (d ₆ -DMSO): δ 10.73 (1H, s), 10.37 (1H,
s), 8.67 (1H, d, J = 8.6Hz), 8.01 (4H, s), 7.78-7.4
8 (4H, m), 7.44-7.20 (3H, m), 7.10-6.80 (3H, m), 4.
53 (2H, s), 4.42-4.22 (1H, m), 3.62-3.40 (2H, m),
3.18 (3H, s), 3.00-2.78 (2H, m), 2.62-2.38 (1H,
m), 2.00-1.65 (2H, m).

Example 49 (119) N-hydroxy-2 (S) -benzyl-5-methoxymethoxy-4 (S)-[N- [4- [3- (4-chlorophenoxy-1-propynyl) phenyl] Carbonyl] amino] pentanamide

Embedded image TLC: Rf 0.26 (chloroform: methanol = 1
9: 1); NMR (d ₆ -DMSO): δ 10.35 (1H, s), 8.67 (1H, s),
8.24 (1H, d, J = 8.4Hz), 7.87 (2H, d, J = 8.4Hz), 7.5
3 (2H, d, J = 8.4Hz), 7.38 (2H, d, J = 9.2Hz), 7.30-7.0
0 (7H, m), 5.08 (2H, s), 4.53 (2H, s), 4.25 (1H,
m), 3.49 (2H, d, J = 5.4Hz), 3.20 (3H, s), 2.77 (2H,
d, J = 7.0Hz), 2.38 (1H, m), 1.90-1.60 (2H, m).

Example 49 (120) N-hydroxy-2 (S) -benzyl-5-methoxymethoxy-4 (S)-[N- (4-phenoxyphenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.39 (chloroform: methanol = 1
9: 1); NMR (d ₆ -DMSO): δ 10.36 (1H, s), 8.09 (1H, d,
J = 8.6Hz), 7.91 (2H, d, J = 8.8Hz), 7.50-7.38 (2H, m),
7.30-7.08 (8H, m), 7.03 (2H, d, J = 8.8Hz), 4.54 (2H,
s), 4.36-4.18 (1H, m), 3.58-3.40 (2H, m), 3.20 (3
H, s), 2.84-2.65 (2H, m), 2.45-2.30 (1H, m), 1.88-
1.58 (2H, m).

Example 49 (121) N-hydroxy-2 (S) -benzyl-5-methoxymethoxy-4 (S)-[N- [4- (4-phenylpiperidin-1-yl) phenylcarbonyl] amino ] Pentanamide

Embedded image TLC: Rf 0.26 (chloroform: methanol = 1
9: 1); NMR (d ₆ -DMSO): δ 10.33 (1H, s), 8.66 (1H, s),
7.82 (1H, d, J = 8.8Hz), 7.77 (2H, d, J = 8.8Hz), 7.3
8-7.06 (10H, m), 6.99 (2H, d, J = 8.8Hz), 4.54 (2H,
s), 4.38-4.16 (1H, m), 4.04-3.90 (2H, m), 3.58-3.4
0 (2H, m), 3.21 (3H, s), 2.96-2.60 (5H, m), 2.44-
2.28 (1H, m), 1.95-1.60 (6H, m).

Example 49 (122) N-hydroxy-2 (S) -benzyl-5-methoxymethoxy-4 (S)-[N- [4- (6-imidazolyl-
1-hexynyl) phenylcarbonyl] amino] pentanamide

Embedded image TLC: Rf 0.46 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.35 (1H, s), 8.67 (1H, s),
8.18 (1H, d, J = 8.4Hz), 7.83 (2H, d, J = 8.4Hz), 7.6
3 (1H, t, J = 1.2Hz), 7.44 (2H, d, J = 8.4Hz), 7.28-7.0
7 (6H, m), 6.89 (1H, t, J = 1.2Hz), 4.53 (2H, s), 4.
36-4.17 (1H, m), 4.01 (2H, t, J = 7.0Hz), 3,60-3.40
(2H, m), 3.20 (3H, s), 2.84-2.70 (2H, m), 2.47 (2
H, t, J = 7.0Hz), 2.46-2.30 (1H, m), 1.96-1.62 (4H,
m), 1.58-1.40 (2H, m).

Example 49 (123) N-hydroxy-2 (S)-(naphthalen-1-yl)
-5-methoxymethoxy-4 (S)-[N- (4-phenoxyphenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.36 (chloroform: methanol = 1
9: 1); NMR (d ₆ -DMSO): δ 10.26 (1H, s), 8.63 (1H, s),
8.16 (1H, d, J = 8.4Hz), 8.04-7.82 (4H, m), 7.80-7.
70 (1H, m), 7.52-7.16 (7H, m), 7.14-6.96 (4H, m),
4.52 (2H, s), 4.50-4.28 (1H, m), 3.61-3.40 (2H,
m), 3.25-3.02 (5H, m), 2.69-2.52 (1H, m), 2.00-1.7
8 (2H, m).

Example 49 (124) N-hydroxy-2 (S)-[4- (benzofuran-2
-Yl) benzyl] -5-methoxymethoxy-4 (S)
-[N- (4-iodophenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.49 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.38 (1H, s), 8.70 (1H, s),
8.25 (1H, d, J = 8.7Hz), 7.85 (2H, d, J = 8.4Hz), 7.79
(2H, d, J = 8.1Hz), 7.70-7.56 (4H, m), 7.36 (1H, s),
7.34-7.20 (4H, m), 4.55 (2H, s), 4.35-4.20 (1H,
m), 3.60-3.45 (2H, m), 3.21 (3H, s), 2.83 (2H, d, J
= 6.9Hz), 2.45-2.30 (1H, m), 1.90-1.60 (2H, m).

Examples 49 (125) to 49 (233) Example 37 → Example 39 → Example 41 (corresponding to methoxymethyl chloride) using the corresponding compound instead of the compound prepared in Reference Example 4. Compound was used.) Example 43 (Using the corresponding compound in place of benzyl bromide) Example 44 The procedure described in Example 49 was followed to obtain the compound shown below.

Example 49 (125) N-hydroxy-2 (S) -benzyl-5-ethoxymethoxy-4 (S)-[N- (trans-4-methylcyclohexylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.36 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.32 (s, 1H), 8.80-8.60 (br
s, 1H), 7.43 (d, J = 8.7Hz, 1H), 7.28-7.19 (m, 2H),
7.19-7.07 (m, 3H), 4.54 (s, 2H), 4.05-3.85 (m, 1
H), 3.60-3.20 (m, 4H), 2.80-2.60 (m, 2H), 2.38-2.2
0 (m, 1H), 2.10-1.90 (m, 1H), 1.80-1.60 (m, 5H),
1.60-1.45 (m, 1H), 1.45-1.20 (m, 3H), 1.11 (t, J =
6.9Hz, 3H), 1.00-0.80 (m, 5H).

Example 49 (126) N-hydroxy-2 (S)-(4-nitrobenzyl)-
5-ethoxymethoxy-4 (S)-[N- (trans-
4-methylcyclohexylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.40 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.34 (s, 1H), 8.80-8.60 (br
s, 1H), 8.12 (d, J = 8.7Hz, 2H), 7.48 (d, J = 8.7H
z, 1H), 7.37 (d, J = 8.7Hz, 2H), 4.57 (s, 2H), 4.10
-3.90 (m, 1H), 3.55-3.25 (m, 4H), 3.00-2.70 (m, 2
H), 2.40-2.25 (m, 1H), 2.10-1.95 (m, 1H), 1.85-1.60
(m, 5H), 1.60-1.20 (m, 4H), 1.11 (t, J = 7.2Hz, 3
H), 1.00-0.80 (m, 5H).

Example 49 (127) N-hydroxy-2 (S)-(indol-3-yl)
-5-ethoxymethoxy-4 (S)-[N- (trans-4-methylcyclohexylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.32 (chloroform: methanol = 1
0: 1); NMR (d ₆ -DMSO): δ 10.73 (brs, 1H), 10.32 (brs,
1H), 8.66 (d, J = 1.5Hz, 1H), 7.49 (d, J = 7.8Hz,
1H), 7.41 (d, J = 8.7Hz, 1H), 7.28 (d, J = 8.1Hz,
1H), 7.05-6.99 (m, 2H), 6.94-6.88 (m, 1H), 4.50
(d, J = 6.9Hz, 1H), 4.47 (d, J = 6.9Hz, 1H), 4.02-
3.902 (m, 1H), 3.40 (q, J = 7.2Hz, 2H), 3.37-3.28
(m, 2H), 2.89-2.71 (m, 2H), 2.48-2.34 (m, 1H), 2.0
5-1.93 (m, 1H), 1.77-1.50 (m, 6H), 1.45-1.20 (m, 3
H), 1.06 (t, J = 7.2Hz, 3H), 0.95-0.80 (m, 2H), 0.
84 (d, J = 6.6 Hz, 3H).

Example 49 (128) N-hydroxy-2 (S) -benzyl-5-ethoxymethoxy-4 (S)-[N-[(pyridin-4-yl) carbonyl] amino] pentanamide

Embedded image TLC: Rf 0.30 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.37 (s, 1H), 8.76-8.63 (m,
3H), 8.43 (d, J = 8.6Hz, 1H), 7.80-7.72 (m, 2H),
7.29-7.08 (m, 5H), 4.58 (s, 2H), 4.34-4.14 (m, 1H),
3.60-3.39 (m, 4H), 2.83-2.65 (m, 2H), 2.42-2.28
(m, 1H), 1.88-1.59 (m, 2H), 1.09 (t, J = 7.0Hz, 3
H).

Example 49 (129) N-hydroxy-2 (S) -benzyl-5-ethoxymethoxy-4 (S)-[N- (4-hydroxyphenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.57 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.34 (s, 1H), 9.96-9.80 (b
r, 1H), 7.83 (d, J = 8.4Hz, 1H), 7.74 (d, J = 9.0H
z, 2H), 7.26-7.08 (m, 5H), 6.79 (d, J = 9.0Hz, 2
H), 4.57 (s, 2H), 4.30-4.17 (m, 1H), 3.58-3.40 (m,
4H), 2.76 (d, J = 6.6Hz, 2H), 2.42-2.32 (m, 1H),
1.82-1.60 (m, 2H), 1.09 (t, J = 7.2Hz, 3H).

Example 49 (130) N-hydroxy-2 (S)-(2-nitrobenzyl)-
5-ethoxymethoxy-4 (S)-[N- (trans-
4-methylcyclohexylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.23 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.35 (s, 1H), 8.71 (s, 1H),
7.92 (dd, J = 8.4,1.2Hz, 1H), 7.61 (td, J = 7.4,
1.2Hz, 1H), 7.50-7.40 (m, 2H), 7.36 (d, J = 7.4Hz,
1H), 4.55 (s, 2H), 3.90-3.75 (m, 1H), 3.55-3.25
(m, 4H, overlap with H2O in DMSO), 3.10-2.90 (m, 2
H), 2.55-2.40 (m, 1H, overlap with DMSO), 2.10-1.9
0 (m, 1H), 1.80-1.55 (m, 6H), 1.50-1.20 (m, 3H),
1.10 (t, J = 7.1Hz, 3H), 1.00-0.75 (m, 5H).

Example 49 (131) N-hydroxy-2 (S)-(3-nitrobenzyl)-
5-ethoxymethoxy-4 (S)-[N- (trans-
4-methylcyclohexylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.38 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.30 (s, 1H), 8.67 (s, 1H),
8.10-8.00 (m, 1H), 7.98 (s, 1H), 7.60-7.46 (m, 3
H), 4.56 (s, 2H), 4.10-3.95 (m, 1H), 3.55-3.30 (m,
4H, overlap with H2O in DMSO), 2.94 (dd, J = 13.
0, 4.7Hz, 1H), 2.80 (dd, J = 13.0, 9.9Hz, 1H), 2.3
0-2.20 (m, 1H), 2.10-1.95 (m, 1H), 1.85-1.60 (m, 5
H), 1.60-1.20 (m, 4H), 1.11 (t, J = 7.1Hz, 3H), 1.
00-0.80 (m, 5H).

Example 49 (132) N-hydroxy-2 (S) -benzyl-5-ethoxymethoxy-4 (S)-[N-[(1-methylpyrrole-2
-Yl) carbonyl] amino] pentanamide

Embedded image TLC: Rf 0.31 (chloroform: methanol = 1
9: 1); NMR (d ₆ -DMSO): δ 10.31 (s, 1H), 8.65 (d, J =
1.2Hz, 1H), 7.59 (d, J = 8.8Hz, 1H), 7.25-7.10 (m,
5H), 6.85-6.90 (m, 1H), 6.78-6.76 (m, 1H), 5.98
(t, J = 3.2Hz, 1H), 4.57 (s, 2H), 4.25-4.08 (m, 1
H), 3.83 (s, 3H), 3.50-3.39 (m, 4H), 2.75 (d, J =
7.0Hz, 2H), 2.45-2.29 (m, 1H), 1.82-1.52 (m, 2H),
1.08 (t, J = 7.0Hz, 3H).

Example 49 (133) N-hydroxy-2 (S) -benzyl-5-ethoxymethoxy-4 (S)-[N- (phenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.34 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.34 (s, 1H), 8.60 (d, J =
1.6Hz, 1H), 8.12 (d, J = 8.8Hz, 1H), 7.85 (dd, J =
8.0Hz, 1.8Hz, 2H), 7.52-7.40 (m, 3H), 7.26-7.09
(m, 5H), 4.57 (s, 2H), 4.33-4.15 (m, 1H), 3.49 (d,
J = 5.4Hz, 2H), 3.45 (q, J = 7.0Hz, 2H), 2.76 (d,
J = 7.0Hz, 2H), 2.44-2.28 (m, 1H), 1.85-1.59 (m,
2H), 1.07 (t, J = 7.0 Hz, 3H).

Example 49 (134) N-hydroxy-2 (S) -benzyl-5-ethoxymethoxy-4 (S)-[N- (4-ethylphenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.50 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.33 (d, J = 1.2 Hz, 1H), 8.
65 (s, 1H), 8.02 (d, J = 8.4Hz, 1H), 7.78 (d, J =
8.2Hz, 2H), 7.30-7.09 (m, 7H), 4.57 (s, 2H), 4.15-
4.32 (m, 1H), 3.50-3.39 (m, 4H), 2.76 (d, J = 7.4H
z, 2H), 2.64 (q, J = 7.4Hz, 2H), 2.42-2.25 (m, 1
H), 1.58-1.82 (m, 2H), 1.17 (t, J = 7.6Hz, 3H), 1.
07 (t, J = 7.4Hz, 3H).

Example 49 (135) N-hydroxy-2 (S) -benzyl-5-ethoxymethoxy-4 (S)-[N- (4-methylphenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.56 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.32 (s, 1H), 8.64 (s, 1H),
8.00 (d, J = 8.7Hz, 1H), 7.73 (d, J = 8.1Hz, 2H),
7.26-7.05 (m, 7H), 4.54 (s, 2H), 4.26-4.15 (m, 1
H), 3.51-3.37 (m, 4H), 2.73 (d, J = 7.2Hz, 2H), 2.
32 (s, 3H), 2.39-2.25 (m, 1H), 1.80-1.58 (m, 2H),
1.05 (t, J = 7.1 Hz, 3H).

Example 49 (136) N-hydroxy-2 (S) -benzyl-5-ethoxymethoxy-4 (S)-[N- (4-nitrophenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.25 (methylene chloride: methanol = 1
9: 1); NMR (d ₆ -DMSO): δ 10.36 (d, J = 1.5 Hz, 1H), 8.
67 (d, J = 1.5Hz, 1H), 8.50 (d, J = 8.4Hz, 1H), 8.
30 (d, J = 9.0Hz, 2H), 8.08 (d, J = 9.0Hz, 2H), 7.2
5-7.11 (m, 5H), 4.56 (s, 2H), 4.23 (m, 1H), 3.50
(d, J = 5.7Hz, 2H), 3.43 (q, J = 7.2Hz, 2H), 2.75
(m, 2H), 2.36 (m, 1H), 1.72 (m, 2H), 1.07 (t, J =
7.2Hz, 3H).

Example 49 (137) N-hydroxy-2 (S) -benzyl-5-ethoxymethoxy-4 (S)-[N- (2,2,3,3-tetramethylcyclopropylcarbonyl) amino] Pentanamide

Embedded image TLC: Rf 0.53 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.32 (d, J = 1.2 Hz, 1H), 8.
69 (d, J = 1.2Hz, 1H), 7.49 (d, J = 8.4Hz, 1H), 7.
24-7.09 (m, 5H), 4.53 (s, 2H), 3.98-3.88 (m, 1H),
3.45 (q, J = 7.2Hz, 2H), 3.37-3.35 (m, 2H), 2.73-
2.66 (m, 3H), 2.35-2.25 (m, 1H), 1.70-1.43 (m, 2
H), 1.18-1.04 (m, 15H).

Example 49 (138) N-hydroxy-2 (S)-(3-methoxybenzyl)
-5-ethoxymethoxy-4 (S)-[N- (4-methylphenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.53 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.33 (d, J = 1.8 Hz, 1H), 8.
67 (d, J = 1.8Hz, 1H), 8.06 (d, J = 9.0Hz, 1H), 7.
76 (d, J = 8.4Hz, 2H), 7.24 (d, J = 8.4Hz, 2H), 7.1
3-7.08 (m, 1H), 6.71-6.66 (m, 3H), 4.56 (s, 2H),
4.17-4.30 (m, 1H), 3.65 (s, 3H), 3.53-3.41 (m, 4H),
2.72 (d, J = 7.2Hz, 2H), 2.40-2.30 (m, 1H), 2.34
(s, 3H), 1.81-1.59 (m, 2H), 1.07 (t, J = 7.2Hz, 3
H).

Example 49 (139) N-hydroxy-2 (S) -benzyl-5-ethoxymethoxy-4 (S)-[N- (1-cyclohexenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.25 (methylene chloride: methanol = 1
9: 1); NMR (d ₆ -DMSO): δ 10.31 (brs, 1H), 8.65 (brs,
1H), 7.28-7.08 (m, 6H), 6.49 (brs, 1H), 4.53 (s, 2
H), 4.05 (m, 1H), 3.43 (q, J = 7.2Hz, 2H), 3.47-3.3
5 (m, 2H), 2.69 (m, 2H), 2.28 (m, 1H), 2.20-2.04
(m, 4H), 1.74-1.46 (m, 6H), 1.09 (t, J = 7.2Hz, 3
H).

Example 49 (140) N-hydroxy-2 (S) -benzyl-5-ethoxymethoxy-4 (S)-[N [(1-cyclohexene-4-
Yl) carbonyl] amino] pentanamide

Embedded image TLC: Rf 0.25 (methylene chloride: methanol = 1
9: 1); NMR (d ₆ -DMSO): δ 10.31 (brs, 1H), 8.67 (brs,
1H), 7.54 (d, J = 8.4Hz, 1H), 7.24-7.08 (m, 5H),
5.64 (m, 2H), 4.53 (s, 2H), 3.95 (m, 1H), 3.43 (q,
J = 7.2Hz, 2H), 3.47-3.28 (m, 2H), 2.75-2.63 (m,
2H), 2.33-1.44 (m, 10H), 1.09 (t, J = 7.2Hz, 3H).

Example 49 (141) N-hydroxy-2 (S) -benzyl-5-ethoxymethoxy-4 (S)-[N- (4-dimethylaminophenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.63 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.33 (s, 1H), 8.65 (s, 1H),
7.78-7.69 (m, 3H), 7.25-7.08 (m, 5H), 6.69 (d, J =
9.0Hz, 2H), 4.58 (s, 2H), 4.29-4.18 (m, 1H), 3.56-
3.41 (m, 4H), 2.97 (s, 6H), 2.77 (d, J = 7.2Hz, 2
H), 2.42-2.32 (m, 1H), 1.82-1.62 (m, 2H), 1.10 (t,
J = 6.9Hz, 3H).

Example 49 (142) N-hydroxy-2 (S) -benzyl-5-ethoxymethoxy-4 (S)-[N- (4-carbamoylphenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.37 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.37 (s, 1H), 8.68 (s, 1H),
8.24 (d, J = 8.7Hz, 1H), 8.08 (s, 1H), 7.98-7.87
(m, 4H), 7.48 (s, 1H), 7.28-7.10 (m, 5H), 4.58 (s,
2H), 4.32-4.19 (m, 1H), 3.58-3.40 (m, 4H), 2.77
(d, J = 6.9Hz, 2H), 2.42-2.32 (m, 1H), 1.83-1.61
(m, 2H), 1.09 (t, J = 7.2Hz, 3H).

Example 49 (143) N-hydroxy-2 (S) -benzyl-5-ethoxymethoxy-4 (S)-[N- (4-methoxycarbonylphenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.31 (chloroform: methanol = 1
9: 1); NMR (d ₆ -DMSO): δ 10.38 (s, 1H), 8.69 (s, 1H),
8.35 (d, J = 8.4Hz, 1H), 8.04 (d, J = 8.8Hz, 2H),
7.98 (d, J = 8.8Hz, 2H), 7.28-7.06 (m, 5H), 4.58
(s, 2H), 4.35-4.18 (m, 1H), 3.89 (s, 3H), 3.60-3.3
9 (m, 4H), 2.77 (d, J = 7.0Hz, 2H), 2.42-2.28 (m,
1H), 1.88-1.59 (m, 2H), 1.09 (t, J = 7.0Hz, 3H).

Example 49 (144) N-hydroxy-2 (S) -benzyl-5-ethoxymethoxy-4 (S)-[N- (cyclopentylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.51 (methylene chloride: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.32 (brs, 1H), 8.68 (brs,
1H), 7.49 (d, J = 8.7Hz, 1H), 7.25-7.08 (m, 5H),
4.53 (s, 2H), 3.92 (m, 1H), 3.43 (q, J = 7.2Hz, 2
H), 3.40-3.35 (m, 2H), 2.72 (dd, J = 13.5, 8.7Hz,
1H), 2.65 (dd, J = 13.5, 5.6Hz, 1H), 2.49 (m, 1H),
2.29 (m, 1H), 1.80-1.40 (m, 10H), 1.09 (t, J = 7.2
Hz, 3H).

Example 49 (145) N-hydroxy-2 (S)-(naphthalen-2-yl)
-5-ethoxymethoxy-4 (S)-[N- (trans-4-methylcyclohexylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.31 (chloroform: methanol = 1
9: 1); NMR (d ₆ -DMSO): δ 10.33 (s, 1H), 7.90-7.73 (m,
3H), 7.60 (s, 1H), 7.54-7.37 (m, 3H), 7.34-7.22
(m, 1H), 4.60-4.46 (m, 2H), 4.12-3.90 (m, 1H), 3.5
2-3.22 (m, 4H), 2.87 (d, J = 6.6Hz, 2H), 2.45-2.28
(m, 1H), 2.17-1.94 (m, 1H), 1.88-1.18 (m, 10H),
1.09 (t, J = 7.0Hz, 3H), 1.00-0.72 (m, 4H).

Example 49 (146) N-hydroxy-2 (S) -benzyl-5-ethoxymethoxy-4 (S)-[N- (4-trifluoromethylphenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.58 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.34 (s, 1H), 8.67 (d, J =
2.1Hz, 1H), 8.38 (d, J = 8.7Hz, 1H), 8.04 (d, J =
8.4Hz, 2H), 7.83 (d, J = 8.4Hz, 2H), 7.25-7.10 (m,
5H), 4.56 (s, 2H), 4.30-4.18 (m, 1H), 3.50-3.36 (m
, 4H), 2.76-2.74 (m, 2H), 2.41-2.30 (m, 1H), 1.81
-1.62 (m, 2H), 1.07 (t, J = 7.2Hz, 3H).

Example 49 (147 ) N-hydroxy-2 (S) -benzyl-5-ethoxymethoxy-4 (S)-[N- (4-iodophenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.45 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.33 (s, 1H), 8.65 (brs, 1
H), 8.19 (d, J = 8.4Hz, 1H), 7.83 (d, J = 8.4Hz, 2
H), 7.63 (d, J = 8.4Hz, 2H), 7.24-7.09 (m, 5H), 4.5
5 (s, 2H), 4.28-4.15 (m, 1H), 3.48-3.39 (m, 4H),
2.74 (d, J = 7.2Hz, 2H), 2.38-2.29 (m, 1H), 1.79-
1.59 (m, 2H), 1.06 (t, J = 7.2Hz, 3H).

Example 49 (148) N-hydroxy-2 (S) -benzyl-5-ethoxymethoxy-4 (S)-[N- [4- (2-iodoethynyl) phenylcarbonyl] amino] pentanamide

Embedded image TLC: Rf 0.37 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.35 (s, 1H), 8.66 (d, J =
1.5Hz, 1H), 8.28 (d, J = 8.4Hz, 1H), 7.90 (d, J =
8.4Hz, 2H), 7.71 (d, J = 8.4Hz, 2H), 7.24-7.10 (m,
5H), 4.56 (s, 2H), 4.29-4.18 (m, 1H), 3.50-3.35
(m, 4H), 2.75 (d, J = 6.9Hz, 2H), 2.40-2.31 (m, 1
H), 1.81-1.61 (m, 2H), 1.07 (t, J = 6.9Hz, 3H).

Example 49 (149) N-hydroxy-2 (S) -benzyl-5-ethoxymethoxy-4 (S)-[N- (cycloheptylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.26 (methylene chloride: methanol = 1
9: 1); NMR (d ₆ -DMSO): δ 10.32 (brs, 1H), 8.68 (brs,
1H), 7.41 (d, J = 8.7Hz, 1H), 7.25-7.08 (m, 5H),
4.53 (s, 2H), 3.90 (m, 1H), 3.43 (q, J = 7.2Hz, 2
H), 3.40-3.30 (m, 2H), 2.68 (m, 2H), 2.33-2.20 (m,
2H), 1.80-1.30 (m, 14H), 1.09 (t, J = 7.2Hz, 3H).

Example 49 (150) N-hydroxy-2 (S) -benzyl-5-ethoxymethoxy-4 (S)-[N- (2-thienylcarbonyl)
Amino] pentanamide

Embedded image TLC: Rf 0.48 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.35 (s, 1H), 8.17 (d, J =
9.0Hz, 1H), 7.79-7.76 (m, 1H), 7.72-7.69 (m, 1H),
7.23-7.06 (m, 6H), 4.54 (s, 2H), 4.19-4.08 (m, 1H),
3.50-3.38 (m, 4H), 2.76-2.67 (m, 2H), 2.40-2.30
(m, 1H), 1.79-1.57 (m, 2H), 1.05 (t, J = 7.2Hz, 3
H).

Example 49 (151) N-hydroxy-2 (R)-(3,4,4-trimethyl-2,5-dioxoimidazolidin-1-yl) methyl-5-ethoxymethoxy-4 (S )-[N- (4-Methylphenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.41 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.63 (s, 1H), 8.78 (s, 1H),
7.99 (d, J = 7.8Hz, 1H), 7.73 (d, J = 8.1Hz, 2H),
7.24 (d, J = 8.1Hz, 2H), 4.57 (s, 2H), 4.10-3.95
(m, 1H), 3.60-3.30 (m, 6H, overlap with H2O in DMS
O), 2.78 (s, 3H), 2.70-2.50 (m, 1H), 2.35 (s, 3H),
1.72 (t, J = 6.9Hz, 2H), 1.30 (s, 3H), 1.28 (s, 3
H), 1.08 (t, J = 6.9 Hz, 3H).

Example 49 (152) N-hydroxy-2 (S) -benzyl-5-ethoxymethoxy-4 (S)-[N-[(2-bromo-5-thienyl) carbonyl] amino] pentanamide

Embedded image TLC: Rf 0.38 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.35 (s, 1H), 8.27 (d, J =
8.7Hz, 1H), 7.60 (d, J = 3.9Hz, 1H), 7.27-7.17 (m,
3H), 7.17-7.06 (m, 3H), 4.53 (s, 2H), 4.14-4.03
(m, 1H), 3.49-3.36 (m, 4H), 2.78-2.63 (m, 2H), 2.3
8-2.27 (m, 1H), 1.77-1.56 (m, 2H), 1.05 (t, J = 6.9
Hz, 3H).

Example 49 (153) N-hydroxy-2 (S) -benzyl-5-ethoxymethoxy-4 (S)-[N- (4-bromophenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.46 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.32 (s, 1H), 8.19 (d, J =
8.4Hz, 1H), 7.78 (d, J = 8.5Hz, 2H), 7.64 (d, J =
8.5Hz, 2H), 7.23-7.06 (m, 5H), 4.54 (s, 2H), 4.24-
4.13 (m, 1H), 3.50-3.36 (m, 4H), 2.76-2.69 (m, 2
H), 2.38- 2.27 (m, 1H), 1.79-1.58 (m, 2H), 1.05
(t, J = 7.0Hz, 3H).

Example 49 (154) N-hydroxy-2 (S) -benzyl-5-ethoxymethoxy-4 (S)-[N- (4-hydroxymethylphenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.25 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.32 (s, 1H), 8.65 (s, 1H),
8.04 (d, J = 8.4Hz, 1H), 7.79 (d, J = 7.8Hz, 2H),
7.35 (d, J = 7.8Hz, 2H), 7.23-7.06 (m, 5H), 5.26
(t, J = 5.7Hz, 1H), 4.55 (s, 2H), 4.52 (d, J = 5.7H
z, 2H), 4.27-4.15 (m, 1H), 3.55-3.37 (m, 4H), 2.76
-2.70 (m, 2H), 2.34 (m, 1H), 1.81-1.59 (m, 2H), 1.
06 (t, J = 7.2Hz, 3H).

Example 49 (155) N-hydroxy-2 (S)-(benzothiophen-3-
Yl) -5-ethoxymethoxy-4 (S)-[N- (trans-4-methylcyclohexylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.37 (chloroform: methanol = 1
9: 1); NMR (d ₆ -DMSO): δ 10.39 (s, 1H), 8.72 (s, 1H),
7.95-7.90 (m, 1H), 7.83-7.76 (m, 1H), 7.48 (d, J =
8.7Hz, 1H), 7.40-7.30 (m, 2H), 7.29 (s, 1H), 4.56-
4.48 (m, 2H), 4.12-3.97 (m, 1H), 3.47-3.28 (m, 4
H), 3.01 (dd, J = 14.4, 9.3Hz, 1H), 2.93 (dd, J = 1
4.4, 5.1Hz, 1H), 2.56-2.41 (m, 1H), 2.09-1.96 (m, 1
H), 1.82-1.53 (m, 6H), 1.48-1.20 (m, 3H), 1.09 (t,
J = 6.9Hz, 3H), 0.98-0.78 (m, 5H).

Example 49 (156) N-hydroxy-2 (S) -benzyl-5-ethoxymethoxy-4 (S)-[N- (4-cyanophenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.32 (chloroform: methanol = 1
9: 1); NMR (d ₆ -DMSO): δ 10.38 (s, 1H), 8.69 (s, 1H),
8.42 (d, J = 8.7Hz, 1H), 8.02 (d, J = 8.4Hz, 2H),
7.94 (d, J = 8.4Hz, 2H), 7.30-7.09 (m, 5H), 4.58
(s, 2H), 4.31-3.97 (m, 1H), 3.57-3.39 (m, 4H), 2.
83-2.68 (m, 2H), 2.42- 2.30 (m, 1H), 1.83-1.61 (m,
2H), 1.09 (t, J = 7.2Hz, 3H).

Example 49 (157) N-hydroxy-2 (S) -benzyl-5-ethoxymethoxy-4 (S)-[N-[(1-acetylpiperidin-4-yl) carbonyl] amino] pentanamide

Embedded image TLC: Rf 0.64 (chloroform: methanol = 5:
1); NMR (d ₆ -DMSO): δ 10.32 (brs, 1H), 7.58 (brd,
J = 9.0Hz, 1H), 7.25-7.08 (m, 5H), 4.53 (s, 2H),
4.32 (brd, J = 9.6Hz, 1H), 3.93 (m, 1H), 3.79 (br
d, J = 12.6Hz, 1H), 3.43 (q, J = 6.9Hz, 2H), 3.35
(m, 2H), 2.98 (brt, J = 12.0Hz, 1H), 2.68 (m, 2H),
2.49 (m, 1H), 2.40-2.20 (m, 2H), 1.98 (s, 3H), 1.7
5-1.30 (m, 6H), 1.09 (t, J = 6.9Hz, 3H).

Example 49 (158) N-hydroxy-2 (S) -benzyl-5-ethoxymethoxy-4 (S)-[N-[(1-methylpiperidine-
4-yl) carbonyl] amino] pentanamide

Embedded image TLC: Rf 0.39 (chloroform: methanol: acetic acid = 7: 2: 1); NMR (d ₆ -DMSO): δ 10.30 (brs, 1H), 8.67 (brs,
1H), 7.48 (brd, J = 9.0Hz, 1H), 7.24-7.07 (m, 5H),
4.52 (s, 2H), 3.93 (m, 1H), 3.42 (q, J = 7.2Hz, 2
H), 3.34 (m, 2H), 2.70 (m, 4H), 2.26 (m, 1H), 2.00
(m, 1H), 2.10 (s, 3H), 1.81-1.45 (m, 8H), 1.08 (t,
J = 7.2Hz, 3H).

Example 49 (159) N-hydroxy-2 (S) -benzyl-5-ethoxymethoxy-4 (S)-[N- (4-formylphenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.36 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.38 (s, 1H), 10.09 (s, 1)
H), 8.69 (s, 1H), 8.38 (d, J = 8.4Hz, 1H), 8.05 (d,
J = 8.4Hz, 2H), 7.99 (d, J = 8.4Hz, 2H), 7.30-7.2
0 (m, 2H), 7.20-7.10 (m, 3H), 4.58 (s, 2H), 4.32-
4.20 (m, 1H), 3.60-3.40 (m, 4H), 2.83-2.70 (m, 2
H), 2.45-2.32 (m, 1H), 1.85-1.62 (m, 2H), 1.09 (t,
J = 6.9Hz, 3H).

Example 49 (160) N-hydroxy-2 (S)-(3-methoxybenzyl)
-5-ethoxymethoxy-4 (S)-[N- (4-nitrophenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.40 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.38 (d, J = 1.8 Hz, 1H), 8.
70 (d, J = 1.8Hz, 1H), 8.51 (d, J = 8.4Hz, 1H), 8.
31 (d, J = 8.9Hz, 2H), 8.09 (d, J = 8.9Hz, 2H), 7.1
8-7.10 (m, 1H), 6.75-6.65 (m, 3H), 4.58 (s, 2H),
4.30-4.20 (m, 1H), 3.69 (s, 3H), 3.60-3.40 (m, 4H),
2.80-2.65 (m, 2H), 2.45-2.30 (m, 1H), 1.85-1.60
(m, 2H), 1.09 (t, J = 7.1Hz, 3H).

Example 49 (161) N-hydroxy-2 (S)-(3-methoxybenzyl)
-5-ethoxymethoxy-4 (S)-[N- (4-chlorophenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.47 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.36 (s, 1H), 8.23 (d, J =
8.4Hz, 1H), 7.89 (d, J = 8.6Hz, 2H), 7.53 (d, J =
8.6Hz, 2H), 7.17-7.08 (m, 1H), 6.80-6.65 (m, 3H),
4.58 (s, 2H), 4.30-4.18 (m, 1H), 3.68 (s, 3H), 3.6
0-3.35 (m, 4H, overlap with H2O in DMSO), 2.80-2.65
(m, 2H), 2.42-2.30 (m, 1H), 1.85-1.60 (m, 2H), 1.
09 (t, J = 6.9Hz, 3H).

Example 49 (162) N-hydroxy-2 (S)-(4-methoxybenzyl)
-5-ethoxymethoxy-4 (S)-[N- (4-methylphenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.49 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.30 (s, 1H), 8.64 (s, 1H),
8.02 (d, J = 8.8Hz, 1H), 7.75 (d, J = 8.4Hz, 2H),
7.24 (d, J = 8.4Hz, 2H), 7.02 (d, J = 8.4Hz, 2H),
6.76 (d, J = 8.4Hz, 2H), 4.56 (s, 2H), 4.12-4.30
(m, 1H), 3.68 (s, 3H), 3.49-3.38 (m, 4H), 2.68 (d,
J = 7.4Hz, 2H), 2.39-2.22 (m, 1H), 2.34 (s, 3H), 1.
82-1.58 (m, 2H), 1.07 (t, J = 7.2Hz, 3H).

Example 49 (163) N-hydroxy-2 (S)-(2-methoxybenzyl)
-5-ethoxymethoxy-4 (S)-[N- (4-methylphenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.51 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.30 (s, 1H), 8.63 (d, J =
1.5Hz, 1H), 7.93 (d, J = 8.4Hz, 1H), 7.74 (d, J =
8.4Hz, 2H), 7.23 (d, J = 8.4Hz, 2H), 7.16-6.76 (m,
4H), 4.55 (s, 2H), 4.19-4.08 (m, 1H), 3.62 (s, 3
H), 3.48-3.38 (m, 4H), 2.71-2.62 (m, 2H), 2.51-2.4
0 (m, 1H), 2.33 (s, 3H), 1.75-1.70 (m, 2H), 1.06
(t, J = 7.2Hz, 3H).

Example 49 (164 ) N-hydroxy-2 (S)-(naphthalen-1-yl)
Methyl-5-ethoxymethoxy-4 (S)-[N- (4
-Methylphenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.44 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.24 (s, 1H), 8.61 (s, 1H),
8.11 (d, J = 8.4Hz, 1H), 7.98 (d, J = 8.4Hz, 1H),
7.86-7.79 (m, 4H), 7.74-7.71 (d, J = 8.4Hz, 1H),
7.44-7.23 (m, 5H), 4.54 (s, 2H), 4.30-4.20 (m, 1
H), 3.50-3.47 (m, 2H), 3.95 (q, J = 7.2Hz, 2H), 3.
29-3.10 (m, 2H), 2.62-2.51 (m, 1H), 1.95-1.75 (m,
2H), 1.04 (t, J = 7.2Hz, 3H).

Example 49 (165) N-hydroxy-2 (S)-(3-methoxybenzyl)
-5-ethoxymethoxy-4 (S)-[N- (trans-4-methylcyclohexylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.56 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.31 (s, 1H), 9.00-8.30 (br
s, 1H), 7.44 (d, J = 8.7Hz, 1H), 7.13 (t, J = 8.0H
z, 1H), 6.80-6.65 (m, 3H), 4.55 (d, J = 6.6Hz, 1
H), 4.51 (d, J = 6.6Hz, 1H), 4.00-3.85 (m, 1H), 3.
70 (s, 3H), 3.44 (q, J = 7.1Hz, 2H), 3.50-3.20 (m,
2H), 2.75-2.50 (m, 2H), 2.30-2.20 (m, 1H), 2.10-1.9
0 (m, 1H), 1.80-1.20 (m, 9H), 1.09 (t, J = 7.1Hz,
3H), 0.84 (d, J = 6.6 Hz, 3H), 1.00-0.80 (m, 2H).

Example 49 (166) N-hydroxy-2 (S) -benzyl-5-ethoxymethoxy-4 (S)-[N- (4-methoxycyclohexylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.40 (methylene chloride: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.30 (brs, 1H), 8.67 (brs,
1H), 7.48 (brd, J = 8.4Hz, 0.4H), 7.41 (brd, J = 8.
4Hz, 0.6H), 7.24-7.08 (m, 5H), 4.53 (s, 2H), 3.93
(m, 1H), 3.43 (q, J = 7.2Hz, 2H), 3.34 (m, 3H), 3.
21 (s, 1.2H), 3.18 (s, 1.8H), 2.67 (m, 2H), 2.30-1.
30 (m, 12H), 1.09 (t, J = 7.2Hz, 3H).

Example 49 (167) N-hydroxy-2 (S)-(benzothiophen-3-
Yl) methyl-5-ethoxymethoxy-4 (S)-[N
-(4-Bromophenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.43 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.38 (d, J = 1.2 Hz, 1H), 8.
68 (d, J = 1.2Hz, 1H), 8.27 (d, J = 8.4Hz, 1H), 7.
91 (d, J = 7.5Hz, 1H), 7.83-7.76 (m, 3H), 7.69-7.66
(m, 2H), 7.34-7.22 (m, 3H), 4.55 (s, 2H), 4.38-4.
25 (m, 1H), 3.49 (d, J = 5.1Hz, 2H), 3.41 (q, J =
7.2Hz, 2H), 3.02-2.98 (m, 2H), 2.56-2.48 (m, 1H),
1.91-1.70 (m, 2H), 1.04 (t, J = 7.2Hz, 3H).

Example 49 (168) N-hydroxy-2 (S)-(benzothiophen-3-
Yl) methyl-5-ethoxymethoxy-4 (S)-[N
-(4-Chlorophenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.44 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.38 (d, J = 1.5 Hz, 1H), 8.
68 (d, J = 1.5Hz, 1H), 8.27 (d, J = 8.4Hz, 1H), 7.
93-7.87 (m, 3H), 7.78 (d, J = 7.5Hz, 1H), 7.55-7.52
(m, 2H), 7.34-7.22 (m, 3H), 4.55 (s, 2H), 4.38-4.
24 (m, 1H), 3.49 (d, J = 5.4Hz, 2H), 3.41 (q, J =
7.2Hz, 2H), 3.04-2.92 (m, 2H), 2.58-2.42 (m, 1H),
1.90-1.70 (m, 2H), 1.05 (t, J = 7.2Hz, 3H).

Example 49 (169) N-hydroxy-2 (S) -benzyl-5-ethoxymethoxy-4 (S)-[N-[(2-chloropyridine-5
-Yl) carbonyl] amino] pentanamide

Embedded image TLC: Rf 0.36 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.35 (s, 1H), 8.81 (d, J =
2.4Hz, 1H), 8.65 (s, 1H), 8.43 (d, J = 9.0Hz, 1H),
8.21 (dd, J = 2.4Hz, 8.5Hz, 1H), 7.61 (d, J = 8.5H
z, 1H), 7.24- 7.07 (m, 5H), 4.54 (s, 2H), 4.24-4.
14 (m, 1H), 3.50-3.37 (m, 4H), 2.79-2.66 (m, 2H),
2.39-2.28 (m, 1H), 1.79-1.60 (m, 2H), 1.05 (t, J =
7.1Hz, 3H).

Example 49 (170) N-hydroxy-2 (S)-(3,5-dimethoxybenzyl) -5-ethoxymethoxy-4 (S)-[N- (4
-Methylphenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.33 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.33 (brs, 1H), 8.67 (brs,
1H), 8.02 (brd, J = 8.7Hz, 1H), 7.76 (d, J = 8.1Hz,
2H), 7.25 (d, J = 8.1Hz, 2H), 6.26 (s, 3H), 4.57
(s, 2H), 4.24 (m, 1H), 3.63 (s, 6H), 3.49 (m, 2H),
3.45 (q, J = 7.2Hz, 2H), 2.68 (brd, J = 7.2Hz, 2
H), 2.34 (s, 3H), 2.34 (m, 1H), 1.80-1.59 (m, 2H),
1.07 (t, J = 7.2Hz, 3H).

Example 49 (171) N-hydroxy-2 (S) -benzyl-5-ethoxymethoxy-4 (S)-[N- (4-methylcyclohexylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.38 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.29 (d, J = 1.5 Hz, 1H), 8.
65 (d, J = 1.5Hz, 1H), 7.42 (brd, J = 8.4Hz, 0.16
H), 7.34 (brd, J = 8.4Hz, 0.84H), 7.23-7.08 (m, 5
H), 4.52 (s, 2H), 3.95 (m, 1H), 3.43 (q, J = 7.2H
z, 2H), 3.35 (m, 2H), 2.68 (m, 2H), 2.30-2.10 (m, 2
H), 1.80-1.30 (m, 11H), 1.08 (t, J = 7.2Hz, 3H),
0.88 (d, J = 6.6Hz, 2.5H), 0.83 (d, J = 6.6Hz, 0.5
H).

Example 49 (172) N-hydroxy-2 (S)-(3-methoxybenzyl)
-5-ethoxymethoxy-4 (S)-[N- (4-cyanophenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.32 (chloroform: methanol = 1
9: 1); NMR (d ₆ -DMSO): δ 10.37 (s, 1H), 8.68 (s, 1H),
8.42 (d, J = 8.4Hz, 1H), 8.02 (d, J = 8.4Hz, 2H),
7.95 (d, J = 8.4Hz, 2H), 7.20-7.08 (m, 1H), 6.76-
6.65 (m, 3H), 4.58 (s, 2H), 4.33-4.15 (m, 1H), 3.
68 (s, 3H), 3.55-3.39 (m, 4H), 2.80-2.56 (m, 2H),
2.43-2.28 (m, 1H), 1.88-1.58 (m, 2H), 1.09 (t, J =
7.2Hz, 3H).

Example 49 (173) N-hydroxy-2 (R)-(3,4,4-trimethyl-2,5-dioxoimidazolidin-1-yl) methyl-5-ethoxymethoxy-4 (S )-[N- (Trans-4-methylcyclohexylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.47 (chloroform: methanol = 1
9: 1); NMR (d ₆ -DMSO): δ 10.59 (s, 1H), 8.78 (s, 1H),
7.43 (d, J = 8.4Hz, 1H), 4.52 (d, J = 6.9Hz, 1H),
4.50 (d, J = 6.9Hz, 1H), 3.77-3.65 (m, 1H), 3.48-
3.33 (m, 4H), 2.76 (s, 3H), 2.52-2.41 (m, 1H), 2.0
3-1.92 (m, 1H), 1.45-1.71 (m, 6H), 1.37-1.20 (m,
1H), 1.27 (s, 3H), 1.26 (s, 3H), 1.08 (t, J = 7.2H
z, 3H), 0.89-0.78 (m, 2H), 0.83 (d, J = 6.3Hz, 3
H).

Example 49 (174) N-hydroxy-2 (R)-(benzofuran-2-yl) methyl-5-ethoxymethoxy-4 (S)-[N-
(Trans-4-methylcyclohexylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.42 (chloroform: methanol = 1
9: 1); NMR (d ₆ -DMSO): δ 10.52 (s, 1H), 8.78 (s, 1H),
7.52-7.42 (m, 3H), 7.23-7.13 (m, 2H), 6.53 (s, 1
H), 4.54 (d, J = 6.6Hz, 1H), 4.51 (d, J = 6.6Hz, 1
H), 3.95-3.82 (m, 1H), 3.46-3.33 (m, 4H), 2.97-2.8
1 (m, 2H), 2.55-2.42 (m, 1H), 2.04-1.95 (m, 1H),
1.74-1.56 (m, 7H), 1.39-1.26 (m, 4H), 1.07 (t, J =
7.2Hz, 3H), 0.84 (d, J = 6.6Hz, 3H).

Example 49 (175) N-hydroxy-2 (S)-(benzothiophen-3-
Yl) methyl-5-ethoxymethoxy-4 (S)-[N
-(4-nitrophenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.36 (chloroform: methanol = 1
9: 1); NMR (d ₆ -DMSO): δ 10.42 (s, 1H), 8.70 (brs, 1
H), 8.55 (d, J = 8.4Hz, 1H), 8.32-8.29 (m, 2H), 8.
11-8.08 (m, 2H), 7.93-7.90 (m, 1H), 7.81-7.78 (m,
1H), 7.34-7.25 (m, 3H), 4.55 (s, 2H), 4.38-4.25
(m, 1H), 3.51 (d, J = 5.7Hz, 2H), 3.41 (q, J = 7.2H
z, 2H), 3.05-2.94 (m, 2H), 2.57-2.53 (m, 1H), 1.91
-1.72 (m, 2H), 1.04 (t, J = 7.2Hz, 3H).

Example 49 (176) N-hydroxy-2 (S) -benzyl-5-ethoxymethoxy-4 (S)-[N- (4-cyanophenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.47 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.34 (s, 1H), 8.66 (s, 1H),
8.22 (d, J = 8.4Hz, 1H), 7.85 (d, J = 8.4Hz, 2H), 7.5
5 (d, J = 8.4Hz, 2H), 7.24-7.09 (m, 5H), 4.56 (s, 2
H), 4.35 (s, 1H), 4.28-4.16 (m, 1H), 3.48 (d, J = 6.
0Hz, 2H), 3.43 (q, J = 6.9Hz, 2H), 2.75 (d, J = 7.2Hz,
2H), 2.40-2.29 (m, 1H), 1.81-1.61 (m, 2H), 1.07
(t, J = 6.9Hz, 3H).

Example 49 (177) N-hydroxy-2 (S) -benzyl-5-ethoxymethoxy-4 (S)-[N- (4-methylidenecyclohexylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.40 (methylene chloride: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.31 (s, 1H), 8.67 (s, 1H),
7.50 (brd, J = 8.7Hz, 1H), 7.25-7.08 (m, 5H), 4.61
(s, 2H), 4.53 (s, 2H), 3.93 (m, 1H), 3.43 (q, J = 6.9
Hz, 2H), 3.35 (m, 2H), 2.68 (m, 2H), 2.25 (m, 4H),
2.05-1.30 (m, 8H), 1.09 (t, J = 6.9Hz, 3H).

Example 49 (178) N-hydroxy-2 (S) -benzyl-5-ethoxymethoxy-4 (S)-[N-[(1-formylpiperidin-4-yl) carbonyl] amino] pentanamide

Embedded image TLC: Rf 0.38 (methylene chloride: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.32 (s, 1H), 8.68 (s, 1H),
7.96 (s, 1H), 7.58 (brd, J = 8.7Hz, 1H), 7.25-7.08
(m, 5H), 4.53 (s, 2H), 4.13 (brd, J = 12.3Hz, 1H),
3.93 (m, 1H), 3.67 (brd, J = 10.5Hz, 1H), 3.43 (q, J
= 6.9Hz, 2H), 3.35 (m, 2H), 3.00 (brt, J = 12.3Hz, 1
H), 2.75-2.20 (m, 5H), 1.80-1.30 (m, 6H), 1.09 (t,
J = 6.9Hz, 3H).

Example 49 (179) N-hydroxy-2 (S) -benzyl-5-ethoxymethoxy-4 (S)-[N-[(1-methyl-1-cyclohexen-4-yl) carbonyl] amino ] Pentanamide

Embedded image TLC: Rf 0.30 (chloroform: methanol = 1
0: 1); NMR (d ₆ -DMSO): δ 10.33 (brs, 1H), 7.53 (d, J =
8.4Hz, 1H), 7.30-7.05 (m, 5H), 5.35 (brs, 1H), 4.5
4 (s, 2H), 4.00-3.85 (m, 1H), 3.60-3.20 (m, 4H),
2.80-2.60 (m, 2H), 2.40-1.40 (m, 10H), 1.60 (s, 3
H), 1.10 (t, J = 7.2Hz, 3H).

Example 49 (180) N-hydroxy-2 (S) -benzyl-5-ethoxymethoxy-4 (S)-[N-[(4-methyl-1-cyclohexenyl) carbonyl] amino] pentanamide

Embedded image TLC: Rf 0.35 (chloroform: methanol = 1
0: 1); NMR (d ₆ -DMSO): δ 10.32 (s, 1H), 8.65 (s, 1H),
7.35-7.00 (m, 6H), 6.46 (brs, 1H), 4.54 (s, 2H),
4.20-3.90 (m, 1H), 3.50-3.20 (m, 4H), 2.80-2.60
(m, 2H), 2.40-2.20 (m, 4H), 1.80-1.50 (m, 5H), 1.2
0-1.00 (m, 1H), 1.09 (t, J = 7.1Hz, 3H), 0.93 (d, J =
6.3Hz, 3H).

Example 49 (181) N-hydroxy-2 (S) -benzyl-5-ethoxymethoxy-4 (S)-[N- (4-fluorophenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.45 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.36 (s, 1H), 8.60-8.55 (b
r, 1H), 8.16 (d, J = 8.7Hz, 1H), 7.94 (dd, J = 9.0, 5.
4Hz, 2H), 7.35-7.20 (m, 4H), 7.20-7.08 (m, 3H), 4.5
8 (s, 2H), 4.30-4.18 (m, 1H), 3.60-3.40 (m, 4H),
2.82-2.70 (m, 2H), 2.42-2.30 (m, 1H), 1.82-1.60 (m,
2H), 1.09 (t, J = 6.9Hz, 3H).

Example 49 (182) N-hydroxy-2 (S) -benzyl-5-ethoxymethoxy-4 (S)-[N- (4-chlorophenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.38 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.36 (s, 1H), 8.80-8.55 (b
r, 1H), 8.22 (d, J = 8.4Hz, 1H), 7.89 (d, J = 8.7Hz, 2
H), 7.53 (d, J = 8.7Hz, 2H), 7.30-7.10 (m, 5H), 4.57
(s, 2H), 4.30-4.15 (m, 1H), 3.60-3.40 (m, 4H), 2.
82-2.70 (m, 2H), 2.42-2.30 (m, 1H), 1.82-1.60 (m,
2H), 1.09 (t, J = 7.1Hz, 3H).

Example 49 (183) N-hydroxy-2 (S) -benzyl-5-ethoxymethoxy-4 (S)-[N- (4-hydroxycyclohexylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.38 (chloroform: methanol: acetic acid = 9: 1: 0.5); NMR (d ₆ -DMSO): δ 10.29 (s, 1H), 7.44 (d, J = 8.
8Hz, 0.4H), 7.35 (d, J = 8.8Hz, 0.6H), 7.26-7.03 (m,
5H), 4.51 (s, 2H), 4.02-3.82 (m, 1H), 3.76-3.67
(m, 1H), 3.41 (q, J = 7.1Hz, 2H), 3.39-3.26 (m, 2H),
2.72-2.62 (m, 2H), 2.33-2.19 (m, 1H), 2.15-1.90
(m, 1H), 1.87-1.24 (m, 10H), 1.07 (t, J = 7.1Hz, 3
H).

Example 49 (184) N-hydroxy-2 (S)-(benzofuran-3-yl) methyl-5-ethoxymethoxy-4 (S)-[N-
(Trans-4-methylcyclohexylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.33 (chloroform: methanol = 1
9: 1); NMR (d ₆ -DMSO): δ 10.41 (s, 1H), 8.74 (s, 1H),
7.76-7.56 (m, 2H), 7.55-7.38 (m, 2H), 7.37-7.15
(m, 2H), 4.58-4.46 (m, 2H), 4.13-3.90 (m, 1H), 3.5
8-3.30 (m, 4H), 2.92-2.62 (m, 2H), 2.50-2.34 (m, 1
H), 2.12-1.92 (m, 1H), 1.82-1.50 (m, 6H), 1.48-1.1
8 (m, 3H), 1.09 (t, J = 7.0Hz, 3H), 1.00-0.70 (m, 5
H).

Example 49 (185) N-hydroxy-2 (S)-(3-methoxybenzyl)
-5-ethoxymethoxy-4 (S)-[N- (4-trifluoromethylphenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.41 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.34 (s, 1H), 8.67 (s, 1H),
8.39 (d, J = 8.7Hz, 1H), 8.05 (d, J = 8.0Hz, 2H), 7.8
3 (d, J = 8.0Hz, 2H), 7.12 (t, J = 8.4Hz, 1H), 6.72-6.6
8 (m, 3H), 4.57 (s, 2H), 4.32-4.15 (m, 1H), 3.66
(s, 3H), 3.51-3.39 (m, 4H), 2.73 (d, J = 7.0Hz, 2H),
2.41-2.27 (m, 1H), 1.82-1.59 (m, 2H), 1.07 (t, J =
7.0Hz, 3H).

Example 49 (186) N-hydroxy-2 (S)-(1-methylindole-
3-yl) methyl-5- (2-methoxyethoxy) methoxy-4 (S)-[N- (trans-4-methylcyclohexylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.33 (chloroform: methanol = 1
9: 1); NMR (d ₆ -DMSO): δ 10.30 (s, 1H), 8.64 (s, 1H),
7.52 (d, J = 7.8Hz, 1H), 7.42 (d, J = 8.4Hz, 1H), 7.3
2 (d, J = 7.8Hz, 1H), 7.11 (t, J = 7.8Hz, 1H), 6.98 (s,
1H), 6.96 (t, J = 7.8Hz, 1H), 4.58-4.48 (m, 2H), 4.
03-3.92 (m, 1H), 3.70 (s, 3H), 3.51-3.25 (m, 6H),
3.23 (s, 3H), 2.89-2.70 (m, 2H), 2.43-2.34 (m, 1
H), 2.08-1.95 (m, 1H), 1.80-1.48 (m, 6H), 1.47-1.2
0 (m, 3H), 0.96-0.78 (m, 5H).

Example 49 (187) N-hydroxy-2 (S) -benzyl-5-ethoxymethoxy-4 (S)-[N-[(1,3-dithiane-2-
Yl) carbonyl] amino] pentanamide

Embedded image TLC: Rf 0.39 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.33 (s, 1H), 8.71 (brs, 1
H), 7.81 (d, J = 8.1Hz, 1H), 7.25-7.08 (m, 5H), 4.51
(s, 2H), 4.41 (s, 1H), 3.47-3.17 (m, 6H), 2.78-2.56
(m, 4H), 2.38-2.27 (m, 1H), 1.98-1.82 (m, 2H),
1.67-1.49 (m, 2H), 1.08 (t, J = 7.0Hz, 3H).

Example 49 (188) N-hydroxy-2 (S)-(3-methoxybenzyl)
-5-ethoxymethoxy-4 (S)-[N- (4-bromophenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.47 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.34 (s, 1H), 8.68 (brs, 1
H), 8.22 (d, J = 8.7Hz, 1H), 7.81-7.68 (m, 2H), 7.68-
7.64 (m, 2H), 7.12 (t, J = 8.1Hz, 1H), 6.71-6.66 (m,
3H), 4.56 (s, 2H), 4.16-4.27 (m, 1H), 3.66 (s, 3
H), 3.48 (d, J = 5.7Hz, 2H), 3.43 (q, J = 6.9Hz, 2H),
2.71 (d, J = 6.0Hz, 2H), 2.39-2.28 (m, 1H), 1.79-1.59
(m, 2H), 1.07 (t, J = 6.9Hz, 3H).

Example 49 (189) N-hydroxy-2 (S)-(3-methoxybenzyl)
-5-ethoxymethoxy-4 (S)-[N-[(2-bromothiophen-5-yl) carbonyl] amino] pentanamide

Embedded image TLC: Rf 0.46 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.35 (s, 1H), 8.68 (s, 1H),
8.28 (d, J = 8.7Hz, 1H), 7.62 (d, J = 4.2Hz, 1H), 7.2
6 (d, J = 4.2Hz, 1H), 7.12 (t, J = 7.8Hz, 1H), 6.72-6.6
6 (m, 3H), 4.55 (s, 2H), 4.18-4.05 (m, 1H), 3.68
(s, 3H), 3.49-3.38 (m, 4H), 2.75-2.62 (m, 2H), 2.3
8-2.26 (m, 1H), 1.78-1.58 (m, 2H), 1.07 (t, J = 7.2H
z, 1H).

Example 49 (190) N-hydroxy-2 (S)-(2-methoxybenzyl)
-5-ethoxymethoxy-4 (S)-[N- (trans-4-methylcyclohexylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.30 (chloroform: methanol = 1
9: 1); NMR (d ₆ -DMSO): δ 10.31 (s, 1H), 8.67 (s, 1H),
7.36 (d, J = 8.0Hz, 1H), 7.21-7.09 (m, 1H), 7.08-7.
00 (m, 1H), 6.89 (d, J = 7.4Hz, 1H), 6.81 (t, J = 7.4H
z, 1H), 4.56-4.48 (m, 2H), 3.90-3.75 (m, 1H), 3.74
(s, 3H), 3.43 (q, J = 7.0Hz, 2H), 3.40-3.24 (m, 2H),
2.80- 2.56 (m, 2H), 2.44-2.28 (m, 1H), 2.09-1.89
(m, 1H), 1.78-1.48 (m, 6H), 1.44-1.17 (m, 3H), 1.1
0 (t, J = 7.0Hz, 3H), 1.00-0.70 (m, 5H).

Example 49 (191) N-hydroxy-2 (S) -benzyl-5-ethoxymethoxy-4 (S)-[N-[(2-methylpyridine-5
-Yl) carbonyl] amino] pentanamide

Embedded image TLC: Rf 0.22 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.33 (s, 1H), 8.86 (d, J = 2.
0Hz, 1H), 8.64 (s, 1H), 8.24 (d, J = 8.8Hz, 1H), 8.
06 (dd, J = 8.0Hz, 2.0Hz, 1H), 7.31 (d, J = 8.0Hz, 1
H), 7.26- 7.06 (m, 5H), 4.55 (s, 2H), 4.30-4.12
(m, 1H), 3.50-3.43 (m, 2H), 3.42 (q, J = 7.0Hz, 2H),
2.78- 2.66 (m, 2H), 2.49 (s, 3H), 2.44-2.27 (m, 1
H), 1.83-1.56 (m, 2H), 1.05 (t, J = 7.0Hz, 3H).

Example 49 (192) N-hydroxy-2 (S)-(benzofuran-3-yl) methyl-5-ethoxymethoxy-4 (S)-[N-
(4-nitrophenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.45 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.43 (s, 1H), 8.71 (brs, 1
H), 8.54 (d, J = 8.4Hz, 1H), 8.31 (d, J = 8.8Hz, 2H),
8.09 (d, J = 8.8Hz, 2H), 7.63-7.60 (m, 1H), 7.49 (d,
J = 7.6Hz, 1H), 7.29-7.13 (m, 2H), 4.55 (s, 2H), 4.
38-4.21 (m, 1H), 3.51 (d, J = 5.6Hz, 2H), 3.42 (q, J
= 7.0Hz, 2H), 2.84 (d, J = 7.4Hz, 2H), 2.40-2.20 (m,
1H), 1.91-1.63 (m, 2H), 1.05 (t, J = 7.0Hz, 3H).

Example 49 (193) N-hydroxy-2 (S) -benzyl-5-ethoxymethoxy-4 (S)-[N- (trans-4-hydroxycyclohexylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.41 (chloroform: methanol: acetic acid = 9: 1: 0.5); NMR (d ₆ -DMSO): δ 10.29 (s, 1H), 8.62 (brs, 1)
H), 7.42 (d, J = 8.7Hz, 1H), 7.24-7.05 (m, 5H), 4.51
(s, 2H), 3.96- 3.85 (m, 1H), 3.51-3.25 (m, 5H), 2.7
3-2.50 (m, 2H), 2.30-2.19 (m, 1H), 2.03-1.91 (m,
1H), 1.85-1.56 (m, 5H), 1.53-1.24 (m, 3H), 1.13-1.
03 (m, 5H).

Example 49 (194) N-hydroxy-2 (S)-(3-chlorobenzyl)-
5-ethoxymethoxy-4 (S)-[N- (4-methylphenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.50 (methylene chloride: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.34 (s, 1H), 8.06 (brd, J =
8.8Hz, 1H), 7.77 (d, J = 8.4Hz, 2H), 7.27-7.03 (m, 6
H), 4.57 (s, 2H), 4.23 (m, 1H), 3.50 (m, 2H), 3.44
(q, J = 7.0Hz, 2H), 2.90 (m, 2H), 2.34 (s, 3H), 2.3
4 (m, 1H), 1.80-1.60 (m, 2H), 1.08 (t, J = 7.0Hz, 3
H).

Example 49 (195) N-hydroxy-2 (S) -benzyl-5-ethoxymethoxy-4 (S)-[N-[(2-hydroxypyridin-5-yl) carbonyl] amino] pentanamide

Embedded image TLC: Rf 0.42 (chloroform: methanol: acetic acid = 9: 1: 0.5); NMR (d ₆ -DMSO): δ 11.93 (brs, 1H), 10.32 (s, 1)
H), 7.98 (d, J = 2.4Hz, 1H), 7.90 (d, J = 8.4Hz, 1H),
7.84 (dd, J = 2.4Hz, 8.4Hz, 1H), 7.24-7.06 (m, 5H),
6.31 (d, J = 9.6Hz, 1H), 4.53 (s, 2H), 4.18-4.02 (m,
1H), 3.45-3.33 (m, 4H), 2.75-2.64 (m, 2H), 2.36-
2.25 (m, 1H), 1.73-1.53 (m, 2H), 1.06 (t, J = 7.0Hz,
3H).

Example 49 (196) N-hydroxy-2 (R)-(3,4,4-trimethyl-2,5-dioxoimidazolidin-1-yl) methyl-5-ethoxymethoxy-4 (S )-[N- (4-Bromophenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.53 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.60 (s, 1H), 8.75 (brs, 1
H), 8.19 (d, J = 7.8Hz, 1H), 7.77-7.74 (m, 2H), 7.66-
7.62 (m, 2H), 4.54 (s, 2H), 4.06-3.96 (m, 1H), 3.50
-3.37 (m, 6H), 2.75 (s, 3H), 2.64-2.51 (m, 1H), 1.
69 (t, J = 7.2Hz, 2H), 1.27 (s, 3H), 1.26 (s, 3H),
1.05 (t, J = 6.9Hz, 3H).

Example 49 (197) N-hydroxy-2 (S)-(3-methoxybenzyl)
-5-ethoxymethoxy-4 (S)-[N- (4-dimethoxymethylphenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.50 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.36 (s, 1H), 8.68 (s, 1H),
8.16 (d, J = 8.4Hz, 1H), 7.89 (d, J = 8.2Hz, 2H), 7.4
6 (d, J = 8.2Hz, 2H), 7.13 (t, J = 8.0Hz, 1H), 6.80-6.6
5 (m, 3H), 5.44 (s, 1H), 4.58 (s, 2H), 4.35-4.20
(m, 1H), 3.66 (s, 3H), 3.60-3.35 (m, 4H), 3.25 (s,
6H), 2.74 (d, J = 6.9Hz, 2H), 2.45-2.30 (m, 1H), 1.8
5-1.60 (m, 2H), 1.09 (t, J = 6.9Hz, 3H).

Example 49 (198) N-hydroxy-2 (S)-(3-trifluoromethyloxybenzyl) -5-ethoxymethoxy-4 (S)-
[N- (4-chlorophenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.38 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.38 (s, 1H), 8.70 (s, 1H),
8.24 (d, J = 8.7Hz, 1H), 7.89 (d, J = 8.7Hz, 2H), 7.5
3 (d, J = 8.7Hz, 2H), 7.36 (t, J = 7.8Hz, 1H), 7.20-7.0
6 (m, 3H), 4.58 (s, 2H), 4.32-4.18 (m, 1H), 3.60-
3.40 (m, 4H), 2.90-2.75 (m, 2H), 2.42-2.30 (m, 1H),
1.85-1.60 (m, 2H), 1.09 (t, J = 7.1Hz, 3H).

Example 49 (199) N-hydroxy-2 (S)-(3-methoxybenzyl)
-5-ethoxymethoxy-4 (S)-[N- [2-nitrothiophen-5-yl) carbonyl] amino] pentanamide

Embedded image TLC: Rf 0.46 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.38 (s, 1H), 8.73-8.69 (m,
2H), 8.13 (d, J = 4.5Hz, 1H), 7.83 (d, J = 4.5Hz, 1
H), 7.16-7.11 (m, 1H), 6.73-6.67 (m, 3H), 4.56 (s,
2H), 4.18-4.09 (m, 1H), 3.69 (s, 3H), 3.49 (d, J =
8.1Hz, 2H), 3.43 (q, J = 7.2Hz, 2H), 2.79-2.63 (m, 2
H), 2.29-2.40 (m, 1H), 1.80-1.59 (m, 2H), 1.07 (t,
J = 7.2Hz, 3H).

Example 49 (200) N-hydroxy-2 (R)-(benzotriazole-1
-Yl) methyl-5-ethoxymethoxy-4 (S)-
[N- (4-nitrophenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.29 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.52 (s, 1H), 8.62 (d, J = 8.
4Hz, 1H), 8.32 (d, J = 9.0Hz, 2H), 8.08 (d, J = 9.0Hz,
2H), 8.00 (d, J = 8.1Hz, 1H), 7.80 (d, J = 8.1Hz, 1
H), 7.51 (t, J = 8.1Hz, 1H), 7.34 (t, J = 8.1Hz, 1H),
4.88 (dd, J = 14.1Hz, 9.0Hz, 1H), 4.75 (dd, J = 14.1H
z, 5.7Hz, 1H), 4.54 (s, 2H), 4.35-4.24 (m, 1H), 3.5
1 (d, J = 5.1Hz, 2H), 3.41 (q, J = 7.2Hz, 2H), 2.95-2.
86 (m, 1H), 1.86-1.81 (m, 2H), 1.05 (t, J = 7.2Hz, 3
H).

Example 49 (201) N-hydroxy-2 (R)-(3,4,4-trimethyl-2,5-dioxoimidazolidin-1-yl) methyl-5-ethoxymethoxy-4 (S )-[N- (4-Nitrophenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.40 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.63 (s, 1H), 8.76 (s, 1H),
8.47 (d, J = 8.1Hz, 1H), 8.28 (d, J = 8.9Hz, 2H), 8.0
3 (d, J = 8.9Hz, 2H), 4.56 (s, 2H), 4.10-3.98 (m, 1
H), 3.60-3.32 (m, 6H), 2.76 (s, 3H), 2.65-2.50 (m,
1H), 1.80-1.65 (m, 2H), 1.28 (s, 3H), 1.27 (s, 3
H), 1.06 (t, J = 7.2Hz, 3H).

Example 49 (202) N-hydroxy-2 (R)-(3,4,4-trimethyl-2,5-dioxoimidazolidin-1-yl) methyl-5-ethoxymethoxy-4 (S )-[N- (4-Chlorophenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.40 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.61 (s, 1H), 8.75 (s, 1H),
8.18 (d, J = 8.1Hz, 1H), 7.82 (d, J = 8.6Hz, 2H), 7.5
0 (d, J = 8.6Hz, 2H), 4.55 (s, 2H), 4.10-3.95 (m, 1
H), 3.60-3.35 (m, 6H), 2.76 (s, 3H), 2.65-2.45 (m,
1H), 1.80-1.62 (m, 2H), 1.28 (s, 3H), 1.26 (s, 3
H), 1.06 (t, J = 6.9Hz, 3H).

Example 49 (203) N-hydroxy-2 (S)-(3-phenylpropyl)
-5-methoxymethoxy-4 (S)-[N- (4-phenoxyphenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.57 (chloroform: methanol = 1
0: 1); NMR (d ₆ -DMSO): δ 10.44 (1H, brs), 8.72 (1H, b
rs), 8.04 (1H, d, J = 8.1Hz), 7.87 (2H, d, J = 8.8Hz),
7.45-7.40 (2H, m), 7.27-7.12 (6H, m), 7.08-7.04
(2H, m), 7.01 (2H, d, J = 8.8Hz), 4.54 (2H, s), 4.14
-4.03 (1H, m), 3.53-3.42 (2H, m), 3.21 (3H, s), 2.6
0-2.40 (2H, m), 2.16-2.06 (1H, m), 1.78-1.60 (2H, m
m), 1.52-1.38 (4H, m).

Example 49 (204) N-hydroxy-2 (S)-(3-phenylpropyl)
-5-methoxymethoxy-4 (S)-[N- [4- [2
E- (4-chlorophenyl) ethenyl] phenylcarbonyl] amino] pentanamide

Embedded image TLC: Rf 0.58 (chloroform: methanol = 1
0: 1); NMR (d ₆ -DMSO): δ 10.46 (1H, brs), 8.74 (1H, b
rs), 8.10 (1H, d, J = 8.7Hz), 7.86 (2H, d, J = 8.3Hz),
7.67 (2H, d, J = 8.3Hz), 7.65 (2H, d, J = 8.8Hz), 7.4
4 (2H, d, J = 8.8Hz), 7.38 (1H, d, J = 16.5Hz), 7.32
(1H, d, J = 16.5Hz), 7.27-7.22 (2H, m), 7.16-7.12 (3
H, m), 4.55 (2H, s), 4.16-4.05 (1H, m), 3.55-3.46
(2H, m), 3.22 (3H, s), 2.59-2.42 (2H, m), 2.17-2.0
7 (1H, m), 1.79-1.62 (2H, m), 1.53-1.41 (4H, m).

Example 49 (205) N-hydroxy-2 (S)-(3-phenylpropyl)
-5-methoxymethoxy-4 (S)-[N- [4- (4
-Phenyl-1,2,5,6-tetrahydropyridine-
1-yl) phenylcarbonyl] amino] pentanamide

Embedded image TLC: Rf 0.31 (chloroform: methanol = 2
0: 1); NMR (d ₆ -DMSO): δ 10.45 (1H, brs), 8.73 (1H, b
rs), 7.80 (1H, d, J = 8.3Hz), 7.77 (2H, d, J = 9.0Hz),
7.48 (2H, d, J = 7.2Hz), 7.36 (2H, t, J = 7.2Hz), 7.2
8-7.22 (3H, m), 7.16-7.12 (3H, m), 6.98 (2H, d, J =
9.0Hz), 6.29 (1H, brs), 4.54 (2H, s), 4.13-4.02 (1
H, m), 3.94 (2H, s), 3.58 (2H, t, J = 5.7Hz), 3.53-
3.42 (2H, m), 3.21 (3H, s), 2.66-2.58 (2H, m), 2.5
8-2.43 (2H, m), 2.18-2.07 (1H, m), 1.78-1.60 (2H, m
m), 1.52-1.40 (4H, m).

Example 49 (206) N-hydroxy-2 (S)-(3-phenyl-2-propenyl) -5-ethoxymethoxy-4 (S)-[N-
(Trans-4-methylcyclohexylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.41 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.43 (s, 1H), 8.73 (brs, 1
H), 7.43 (d, J = 8.4Hz, 1H), 7.33-7.24 (m, 4H), 7.20-
7.14 (m, 1H), 6.33 (d, J = 15.9Hz, 1H), 6.08 (dt, J = 1
5.9, 6.9Hz, 1H), 4.53 (s, 2H), 3.90-3.78 (m, 1H),
3.44 (q, J = 7.1Hz, 2H), 3.40-3.31 (m, 2H), 2.31-2.2
2 (m, 2H), 2.19-2.08 (m, 1H), 2.03-1.92 (m, 1H),
1.74-1.58 (m, 5H), 1.56-1.43 (m, 1H), 1.40-1.18
(m, 3H), 1.06 (t, J = 7.1Hz, 3H), 0.91-0.81 (m, 5
H).

Example 49 (207) N-hydroxy-2 (S)-(3-phenylpropyl)
-5-ethoxymethoxy-4 (S)-[N- (trans-4-methylcyclohexylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.51 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.40 (s, 1H), 8.65 (brs, 1
H), 7.38 (d, J = 8.4Hz, 1H), 7.26-7.20 (m, 2H), 7.16-
7.08 (m, 3H), 4.53 (s, 2H), 3.83-3.72 (m, 1H), 3.49
-3.27 (m, 4H), 2.58-2.38 (m, 2H), 2.04-1.89 (m, 2
H), 1.77-1.52 (m, 5H), 1.50-1.21 (m, 8H), 1.07 (t,
J = 6.9Hz, 3H), 0.91-0.77 (m, 5H).

Example 49 (208) N-hydroxy-2 (S)-(2-phenylethyl)-
5- (2-methoxyethoxy) methoxy-4 (S)-
[N- (trans-4-methylcyclohexylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.34 (chloroform: methanol = 1
0: 1); NMR (d ₆ -DMSO): δ 10.45 (s, 1H), 9.20-8.40 (br
s, 1H), 7.39 (d, J = 8.4Hz, 1H), 7.28-7.23 (m, 2H),
7.20-7.10 (m, 3H), 4.57 (s, 2H). 3.90-3.80 (m, 1H),
3.60-3.20 (m, 6H), 3.22 (s, 3H), 2.60-2.30 (m, 2
H), 2.10-2.00 (m, 1H), 2.05-1.90 (m, 1H), 1.80-1.4
0 (m, 9H), 1.40-1.20 (m, 2H), 0.95-0.75 (m, 2H),
0.84 (d, J = 6.6Hz, 3H).

Example 49 (209) N-hydroxy-2 (S)-(4-phenylbutyl)-
5- (2-methoxyethoxy) methoxy-4 (S)-
[N- (trans-4-methylcyclohexylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.36 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.38 (s, 1H), 7.39 (d, J = 8.
4Hz, 1H), 7.30-7.20 (m, 2H), 7.20-7.10 (m, 3H), 4.5
7 (s, 2H), 3.90-3.75 (m, 1H), 3.65-3.15 (m, 6H),
3.22 (s, 3H), 2.60-2.40 (m, 2H), 2.05-1.90 (m, 2
H), 1.85-1.05 (m, 15H), 0.95-0.75 (m, 2H), 0.84
(d, J = 6.3Hz, 3H).

Example 49 (210) N-hydroxy-2 (S)-(3-phenylpropyl)
-5-ethoxymethoxy-4 (S)-[N- (4-bromophenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.33 (chloroform: methanol = 1
9: 1); NMR (d ₆ -DMSO): δ 10.44 (s, 1H), 8.72 (s, 1H),
8.16 (d, J = 8.2Hz, 1H), 7.79 (d, J = 8.4Hz, 2H), 7.6
5 (d, J = 8.4Hz, 2H), 7.32-7.08 (m, 5H), 4.59 (s, 2
H), 4.20-3.98 (m, 1H), 3.63-3.40 (m, 4H), 2.68-2.3
8 (m, 2H), 2.20- 2.01 (m, 1H), 1.82-1.61 (m, 2H),
1.60-1.30 (m, 4H), 1.08 (t, J = 7.0Hz, 3H).

Example 49 (211) N-hydroxy-2 (S)-(3-phenylpropyl)
-5-ethoxymethoxy-4 (S)-[N- (4-nitrophenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.29 (chloroform: methanol = 1
9: 1); NMR (d ₆ -DMSO): δ 10.45 (s, 1H), 8.72 (s, 1H),
8.45 (d, J = 8.4Hz, 1H), 8.29 (d, J = 9.0Hz, 2H),
8.06 (d, J = 9.0Hz, 2H), 7.29-7.20 (m, 2H), 7.19-
7.09 (m, 3H), 4.59 (s, 2H), 4.17-4.01 (m, 1H), 3.5
6-3.40 (m, 4H), 2.61-2.40 (m, 2H), 2.16-2.03 (m, 1
H), 1.80-1.60 (m, 2H), 1.58-1.32 (m, 4H), 1.07 (t,
J = 7.2Hz, 3H).

Example 49 (212) N-hydroxy-2 (R)-(2-phenoxyethyl)
-5-ethoxymethoxy-4 (S)-[N- (4-nitrophenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.35 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.51 (s, 1H), 8.76 (s, 1H),
8.47 (d, J = 8.4Hz, 1H), 8.29 (d, J = 8.9Hz, 2H), 8.0
7 (d, J = 8.9Hz, 2H), 7.30-7.20 (m, 2H), 6.95-6.80
(m, 3H), 4.59 (s, 2H), 4.25-4.12 (m, 1H), 3.95-3.7
8 (m, 2H), 3.60-3.40 (m, 4H), 2.40-2.25 (m, 1H),
2.00-1.65 (m, 4H), 1.07 (t, J = 7.1Hz, 3H).

Example 49 (213) N-hydroxy-2 (R)-(2-pyridyl) methyl-
5-methoxymethoxy-4 (S)-[N- (4-phenoxyphenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.20 (chloroform: methanol = 1
9: 1); NMR (d ₆ -DMSO): δ 10.44 (1H, s), 8.69 (1H, s),
8.48-8.40 (1H, m), 8.06 (1H, d, J = 8.4Hz), 7.88 (2
H, d, J = 8.8Hz), 7.65 (1H, td, J = 7.8, 1.8Hz), 7.50-
7.38 (2H, m), 7.24- 7.12 (3H, m), 7.11-7.04 (2H, m
m), 7.02 (2H, d, J = 8.8Hz), 4.52 (2H, s), 4.23-4.02
(1H, m), 3.49 (2H, d, J = 5.6Hz), 3.19 (3H, s), 2.96
(1H, dd, J = 13.8, 8.4Hz), 2.85 (1H, dd, J = 13.8, 6.
6Hz), 2.75-2.60 (1H, m), 1.77 (2H, t, J = 7.0Hz).

Example 49 (214) N-hydroxy-2 (R)-(2-pyridyl) methyl-
5-methoxymethoxy-4 (S)-[N- [4- (benzofuran-2-yl) phenylcarbonyl] amino] pentanamide

Embedded image TLC: Rf 0.45 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.70-10.40 (1H, brs), 9.00-
8.60 (1H, brs), 8.50-8.25 (2H, m), 7.99 (4H, s),
7.80-7.44 (4H, m), 7.41-7.06 (4H, m), 4.52 (2H, s),
4.31-4.10 (1H, m), 3.64-3.46 (2H, m), 3.19 (3H,
s), 3.06-2.82 (2H, m), 2.80-2.63 (1H, m), 2.00-1.7
0 (2H, m).

Example 49 (215) N-hydroxy-2 (S)-(3-pyridyl) methyl-
5-methoxymethoxy-4 (S)-[N- (4-phenoxyphenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.43 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.36 (1H, s), 8.69 (1H, s),
8.40-8.32 (2H, m), 8.12 (1H, d, J = 9.4Hz), 7.91 (2
H, d, J = 8.8Hz), 7.54-7.38 (3H, m), 7.29-7.17 (2H,
m), 7.12-7.06 (2H, m), 7.03 (2H, d, J = 8.8Hz), 4.56
(2H, s), 4.40-4.20 (1H, m), 3.60-3.42 (2H, m), 3.
22 (3H, s), 2.87 (1H, dd, J = 13.6, 4.8Hz), 2.75 (1
H, dd, J = 13.6, 9.6Hz), 2.43-2.28 (1H, m), 1.90-1.5
9 (2H, m).

Example 49 (216) N-hydroxy-2 (S)-(3-pyridyl) methyl-
5-methoxymethoxy-4 (S)-[N- [4- [2-
(4-methylphenyl) ethynyl] phenylcarbonyl] amino] pentanamide

Embedded image TLC: Rf 0.40 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.37 (1H, s), 8.70 (1H, s),
8.40-8.33 (2H, m), 8.29 (1H, d, J = 8.0Hz), 7.92 (2
(H, d, J = 8.4Hz), 7.63 (2H, d, J = 8.4Hz), 7.57-7.42
(3H, m), 7.31- 7.20 (3H, m), 4.56 (2H, s), 4.40-4.
20 (1H, m), 3.62-3.44 (2H, m), 3.22 (3H, s), 2.87
(1H, dd, J = 13.6, 4.8Hz), 2.76 (1H, dd, J = 13.6, 9.2
Hz), 2.42-2.26 (4H, m), 1.91-1.59 (2H, m).

Example 49 (217) N-hydroxy-2 (S)-(3-pyridyl) methyl-
5-methoxymethoxy-4 (S)-[N- [4- (1-
Heptynyl) phenylcarbonyl] amino] pentanamide

Embedded image TLC: Rf 0.34 (chloroform: methanol: acetic acid: water = 100: 10: 1: 1); NMR (d ₆ -DMSO): δ 10.35 (1H, brs), 8.69 (1H, br)
s), 8.37-8.33 (2H, m), 8.23 (1H, d, J = 8.4Hz), 7.83 (2H
H, d, J = 8.0Hz), 7.51-7.43 (3H, m), 7.25 (1H, dd, J = 7.
8Hz, 4.8Hz), 4.54 (2H, s), 4.38-4.15 (1H, m), 3.50 (2
(H, d, J = 5.4Hz), 3.20 (3H, s), 2.92-2.68 (2H, m), 2.
49-2.39 (1H, m), 1.91-1.20 (10H, m), 0.88 (3H, t, J =
7.0Hz).

Example 49 (218) N-hydroxy-2 (S)-(3-pyridyl) methyl-
5-methoxymethoxy-4 (S)-[N- [4- [2E
-(4-Chlorophenyl) ethenyl] phenylcarbonyl] amino] pentanamide

Embedded image TLC: Rf 0.26 (chloroform: methanol: acetic acid: water = 100: 10: 1: 1); NMR (d ₆ -DMSO): δ 10.40 (1H, brs), 8.72 (1H, br)
s), 8.35 (2H, s), 8.21 (1H, d, J = 8.7Hz), 7.89 (2H, d,
J = 8.4Hz), 7.68 (2H, d, 8.4Hz), 7.65 (2H, d, J = 8.7H
z), 7.51 (1H, d, J = 7.2Hz), 7.44 (2H, d, J = 8.7Hz), 7.
39 (1H, d, J = 16.8Hz), 7.32 (1H, d, J = 16.8Hz), 7.27-
7.23 (1H, m), 4.55 (2H, s), 4.39-4.21 (1H, m), 3.61-
3.42 (2H, m), 3.21 (3H, s), 2.91-2.69 (2H, m), 2.45-
2.31 (1H, m), 1.91-1.60 (2H, m).

Example 49 (219) N-hydroxy-2 (S)-(3-pyridyl) methyl-
5-methoxymethoxy-4 (S)-[N- (trans-
4-methylcyclohexylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.34 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.34 (1H, brs), 8.72 (1H, b
rs), 8.36 (1H, dd, J = 4.8, 1.5Hz), 8.32-8.30 (1H,
m), 7.52-7.45 (2H, m), 7.29-7.22 (1H, m), 4.51 (2
H, s), 4.05-3.93 (1H, m), 3.44-3.35 (2H, m), 3.22
(3H, s), 2.77 (1H, dd, J = 13.2, 4.8Hz), 2.69 (1H, d
d, J = 13.2, 9.6Hz), 2.35-2.22 (1H, m), 2.10-1.97 (1
H, m), 1.82-1.61 (5H, m), 1.60-1.44 (1H, m), 1.43-
1.20 (3H, m), 0.97-0.79 (5H, m).

Example 49 (220) N-hydroxy-2 (S)-(4-pyridyl) methyl-
5-methoxymethoxy-4 (S)-[N- (4-phenoxyphenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.27 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.44-10.30 (1H, brs), 8.75-
8.62 (1H, brs), 8.40 (2H, d, J = 6.0Hz), 8.13 (1H, d,
J = 8.4Hz), 7.91 (2H, d, J = 8.7Hz), 7.48-7.38 (2H,
m), 7.22-7.18 (1H, m), 7.13 (2H, d, J = 6.0Hz), 7.06
(2H, d, J = 7.8Hz), 7.02 (2H, d, J = 8.7Hz), 4.55 (2
H, s), 4.34-4.21 (1H, m), 3.58-3.42 (2H, m), 3.22
(3H, s), 2.91-2.71 (2H, m), 2.46-2.32 (1H, m), 1.8
5-1.61 (2H, m).

Example 49 (221) N-hydroxy-2 (R)-(2-pyridyl) methyl-
5- (2-methoxyethoxy) methoxy-4 (S)-
[N- (4-phenoxyphenylcarbonyl) amino]
Pentanamide

Embedded image TLC: Rf 0.38 (chloroform: methanol: acetic acid: water = 100: 10: 1: 1); NMR (d ₆ -DMSO): δ 10.43 (1H, s), 8.69 (1H, s),
8.45 (1H, d, J = 4.5Hz), 8.60 (1H, d, J = 8.4Hz), 7.87 (2
H, d, J = 8.4Hz), 7.65 (1H, t, J = 7.5Hz), 7.42 (2H, t,
J = 8.1Hz), 7.21-7.15 (3H, m), 7.08-7.00 (4H, m), 4.58
(2H, s), 4.06-4.22 (1H, m), 3.43-3.60 (4H, m), 3.42
-3.38 (2H, m), 3.20 (3H, s), 2.98-2.81 (2H, m), 2.61-
2.78 (1H, m), 1.75 (2H, t, J = 7.2Hz).

Example 49 (222) N-hydroxy-2 (S)-(3-pyridyl) methyl-
5-ethoxymethoxy-4 (S)-[N- (2-methylphenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.38 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO + CD ₃ OD (5 drops)): δ 8.36-8.32 (m,
2H), 7.50 (d, J = 7.5Hz, 1H), 7.34 (d, J = 7.5Hz, 1
H), 7.31-7.14 (m, 4H), 4.59 (2H, s), 4.26-4.16 (m,
1H), 3.52-3.43 (m, 4H), 2.87- 2.69 (m, 2H), 2.43
-2.34 (m, 1H), 2.31 (s, 3H), 1.77-1.57 (m, 2H), 1.
09 (t, J = 6.9Hz, 3H).

Example 49 (223) N-hydroxy-2 (S)-(3-pyridyl) methyl-
5-ethoxymethoxy-4 (S)-[N- (3-methylphenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.38 (chloroform: methanol = 9:
1); NMR (CD ₃ OD): δ 8.44-8.37 (m, 2H), 7.75-7.66
(m, 3H), 7.42-7.34 (m, 3H), 4.73 (s, 2H), 4.52-4.4
1 (m, 1H), 3.71- 3.57 (m, 4H), 3.13-2.88 (m, 2H),
2.55-2.42 (m, 4H), 2.06-1.90 (m, 2H), 1.21 (t, J = 7
.2Hz, 3H).

Example 49 (224 ) N-hydroxy-2 (S)-(3-pyridyl) methyl-
5-ethoxymethoxy-4 (S)-[N- (4-methylphenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.38 (chloroform: methanol = 9:
1); NMR (CD ₃ OD + d ₆ -DMSO (5 drops)): δ 8.46-8.42 (m,
2H), 7.84 (d, J = 8.4Hz, 2H), 7.72 (d, J = 7.8Hz, 1
H), 7.42-7.33 (m, 3H), 4.75 (s, 2H), 4.53-4.44 (m,
1H), 3.71-3.59 (m, 4H), 3.13- 2.88 (m, 2H), 2.57-
2.45 (m, 4H), 2.09-1.88 (m, 2H), 1.23 (t, J = 7.2Hz,
3H).

Example 49 (225) N-hydroxy-2 (S)-(3-pyridyl) methyl-
5-ethoxymethoxy-4 (S)-[N- (4-methoxyphenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.30 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.35 (s, 1H), 8.68 (s, 1H),
8.40-8.30 (m, 2H), 8.00 (d, J = 8.8Hz, 1H), 7.86 (d,
J = 8.8Hz, 2H), 7.53-7.44 (m, 1H), 7.28-7.20 (m, 1
H), 6.99 (d, J = 8.8Hz, 2H), 4.59 (s, 2H), 4.38-4.17
(m, 1H), 3.81 (s, 3H), 3.60-3.40 (m, 4H), 2.86 (d
d, J = 13.2, 5.2Hz, 1H), 2.74 (dd, J = 13.2, 9.2Hz, 1
H), 2.44-2.28 (m, 1H), 1.90-1.58 (m, 2H), 1.09 (t,
J = 6.8Hz, 3H).

Example 49 (226) N-hydroxy-2 (S)-(3-pyridyl) methyl-
5-ethoxymethoxy-4 (S)-(N-cyclohexylcarbonylamino) pentanamide

Embedded image TLC: Rf 0.21 (chloroform: methanol = 1
0: 1); NMR (d ₆ -DMSO): δ 10.33 (brs, 1H), 8.70 (brs,
1H), 8.36 (dd, J = 1.8, 4.5Hz, 1H), 8.30 (d, J = 1.8H
z, 1H), 7.48-7.45 (m, 2H), 7.26 (dd, J = 4.5,7.6Hz,
1H), 4.55 (s, 2H), 4.40-3.51 (m, 1H), 3.45 (q, J =
7.2Hz, 2H), 3.83-3.32 (m, 2H), 2.80-2.63 (m, 2H),
2.32-2.21 (m, 1H), 2.14-2.03 (m, 1H), 1.78-1.45 (m,
7H), 1.40-1.06 (m, 5H), 1.10 (t, J = 6.9Hz, 3H).

Example 49 (227) N-hydroxy-2 (S)-(3-pyridyl) methyl-
5-ethoxymethoxy-4 (S)-[N- (4-nitrophenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.22 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.36 (s, 1H), 8.69 (s, 1H),
8.53 (d, J = 8.7Hz, 1H), 8.37-8.29 (m, 3H), 8.10-8.
06 (m, 2H), 7.52-7.48 (m, 1H), 7.28-7.23 (m, 1H),
4.58 (s, 2H), 4.21-4.32, (m, 1H), 3.52 (d, J = 5.7H
z, 2H), 3.45 (q, J = 7.2Hz, 2H), 2.86-2.69 (m, 2H),
2.42-2.23 (m, 1H), 1.85-1.62 (m 2H), 1.08 (t, J =
7.2Hz, 3H).

Example 49 (228) N-hydroxy-2 (S)-(3-pyridyl) methyl-
5-ethoxymethoxy-4 (S)-[N- (4-bromophenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.32 (chloroform: methanol: acetic acid = 90: 10: 1); NMR (d ₆ -DMSO): δ 10.34 (s, 1H), 8.68 (s, 1H),
8.37-8.24 (m, 3H), 7.80 (d, J = 8.7Hz, 2H), 7.67 (d,
J = 8.7Hz, 2H), 7.49 (dt, J = 8.1Hz, 1.8Hz, 1H), 4.57
(s, 2H), 4.31-4.18 (m, 1H), 3.50 (d, J = 6.0Hz, 2H),
3.45 (q, J = 7.2Hz, 2H), 2.87-2.68 (m, 2H), 2.40-2.
24 (m, 1H), 1.82-1.59 (m, 2H), 1.07 (t, J = 7.2Hz, 3
H).

Example 49 (229) N-hydroxy-2 (S)-(3-quinolyl) methyl-
5-ethoxymethoxy-4 (S)-[N- (trans-
4-methylcyclohexylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.37 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.31 (s, 1H), 8.67-8.65 (m,
2H), 7.98-7.83 (m, 3H), 7.73-7.49 (m, 3H), 4.55
(s, 2H), 4.13-3.97 (m, 1H), 3.43 (q, J = 7.0Hz, 2H),
3.42-3.36 (m, 2H), 3.06-2.80 (m, 2H), 2.48-2.30
(m, 1H), 2.15-1.98 (m, 1H), 1.81-1.26 (m 9H), 1.08
(t, J = 7.0Hz, 3H), 0.99-0.79 (m, 2H), 0.85 (d, J = 7.
0Hz, 3H).

Example 49 (230) N-hydroxy-2 (S) -phenylthio-5-methoxymethoxy-4 (S)-[N- (4-phenoxyphenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.27 (chloroform: methanol: acetic acid = 100: 5: 1); NMR (d ₆ -DMSO): δ 10.69 (1H, s), 8.97 (1H, s),
8.17 (1H, d, J = 8.0Hz), 7.86 (2H, d, J = 8.8Hz), 7.47-7.
39 (4H, m), 7.34-7.16 (4H, m), 7.08-6.99 (4H, m), 4.53
(2H, s), 4.38-4.25 (1H, m), 3.62-3.35 (3H, m), 3.19
(3H, s), 2.02 (2H, t, J = 6.8Hz).

Example 49 (231) N-hydroxy-2 (S) -phenylthio-5-ethoxymethoxy-4 (S)-[N- (trans-4-methylcyclohexylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.37 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.67 (s, 1H), 8.94 (brs, 1
H), 7.52 (d, J = 8.1Hz, 1H), 7.38-7.22 (m, 5H), 4.52
(s, 2H), 4.04-3.93 (m, 1H), 3.52-3.24 (m, 5H), 2.01
-1.78 (m, 3H), 1.69-1.55 (m, 4H), 1.36-1.19 (m, 3
H), 1.07 (t, J = 7.0Hz, 3H), 0.91-0.75 (m, 5H).

Example 49 (232) N-hydroxy-2 (S) -methylthio-5-ethoxymethoxy-4 (S)-[N- (trans-4-methylcyclohexylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.38 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.56 (s, 1H), 8.88 (s, 1H),
7.48 (d, J = 8.4Hz, 1H), 4.55 (s, 2H), 4.04-3.90
(m, 1H), 3.46 (q, J = 7.1Hz, 2H), 3.39-3.25 (m, 2H),
2.96-2.87 (m, 1H), 2.04-1.91 (m, 4H), 1.90-1.77
(m, 1H), 1.76-1.55 (m, 5H), 1.40-1.18 (m, 3H), 1.0
8 (t, J = 7.1Hz, 3H), 0.92-0.74 (m, 5H).

Example 49 (233) N-hydroxy-2 (S)-(4-pyridyl) thio-5
-Ethoxymethoxy-4 (S)-[N- (trans-4
-Methylcyclohexylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.29 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.87 (s, 1H), 9.08 (s, 1H),
8.35 (d, J = 6.0Hz, 2H), 7.58 (d, J = 8.1Hz, 1H), 7.2
7 (d, J = 6.0Hz, 2H), 4.56 (s, 2H), 3.99-3.88 (m, 1
H), 3.78 (t, J = 7.4Hz, 1H), 3.45 (q, J = 7.2Hz, 2H),
3.42-3.31 (m, 2H), 2.02-1.87 (m, 3H), 1.71-1.56
(m, 4H), 1.35-1.17 (m, 3H), 1.07 (t, J = 7.2Hz, 3H),
0.91-0.76 (m, 5H).

Embodiments 49 (234) to 49 (253) Embodiments 44 (8), 44 (9), 44 (11), 44
(14), 44 (17) -44 (21), 44 (24)
Using the compound prepared in -44 (26) or the corresponding compound in place of the compound prepared in Reference Example 4, Example 37 → Example 39 → Example 41 → Example 43 (instead of benzyl bromide) The corresponding compound was used.) → The compound obtained by the same procedure as in Example 44 was operated in the same manner as in Example 49 to obtain the compound shown below. .

Example 49 (234) N-hydroxy-2 (S) -hydroxy-5-methoxymethoxy-4 (S)-[N- (4-phenoxyphenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.57 (chloroform: methanol: acetic acid = 85: 15: 1); NMR (d ₆ -DMSO): δ 10.44 (1H, s), 8.69 (1H, brs),
8.19 (1H, d, J = 8.4Hz), 8.89 (2H, d, J = 8.8Hz), 7.48-
7.38 (2H, m), 7.22-7.16 (1H, m), 7.09-7.01 (4H, m),
5.36 (1H, brs), 4.55 (2H, s), 4.41-4.24 (1H, m), 3.87
(1H, dd, J = 9.8Hz, 2.6Hz), 3.56-3.42 (2H, m), 3.22 (3
H, s), 1.96-1.66 (2H, m).

Example 49 (235) N-hydroxy-2 (R) -hydroxymethyl-5-ethoxymethoxy-4 (S)-[N- (4-chlorophenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.23 (chloroform: methanol: acetic acid = 90: 10: 1); NMR (d ₆ -DMSO): δ 10.55-10.10 (brs, 1H), 8.90-
8.50 (brs, 1H), 8.21 (d, J = 8.4Hz, 1H), 7.86 (d, J =
8.7Hz, 2H), 7.52 (d, J = 8.7Hz, 2H), 4.59 (s, 2H),
4.20-4.00 (m, 1H), 3.60-3.38 (m, 6H), 2.30-2.18
(m, 1H), 1.85-1.70 (m, 1H), 1.70-1.55 (m, 1H), 1.0
9 (t, J = 7.1Hz, 3H).

Example 49 (236) N-hydroxy-2 (R) -methoxymethyl-5-ethoxymethoxy-4 (S)-[N- (4-nitrophenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.22 (chloroform: methanol = 1
9: 1); NMR (d ₆ -DMSO): δ 10.46 (s, 1H), 8.75 (s, 1H),
8.48 (d, J = 8.4Hz, 1H), 8.29 (d, J = 8.8Hz, 2H), 8.0
6 (d, J = 8.8Hz, 2H), 4.59 (s, 2H), 4.22-4.00 (m, 1
H), 3.58-3.25 (m, 6H), 3.18 (s, 3H), 2.43-2.31 (m,
1H), 1.83-1.54 (m, 2H), 1.08 (t, J = 7.0Hz, 3H).

Example 49 (237) N-hydroxy-2 (R) -benzyloxymethyl-5
-Ethoxymethoxy-4 (S)-[N- (4-nitrophenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.35 (chloroform: methanol = 1
9: 1); NMR (d ₆ -DMSO): δ 10.52 (s, 1H), 8.79 (s, 1H),
8.50 (d, J = 8.7Hz, 1H), 8.30 (d, J = 8.7Hz, 2H), 8.0
7 (d, J = 8.7Hz, 2H), 7.40-7.22 (m, 5H), 4.60 (s, 2
H), 4.47 (d, J = 12.0Hz, 1H), 4.41 (d, J = 12.0Hz, 1
H), 4.20-4.07 (m, 1H), 3.61-3.42 (m, 6H), 2.53-2.40
(m, 1H), 1.89-1.78 (m, 1H), 1.77-1.62 (m, 1H), 1.0
8 (t, J = 7.2Hz, 3H).

Example 49 (238) N-hydroxy-2 (R)-(2-methoxyethoxy)
Methyl-5-ethoxymethoxy-4 (S)-[N- (4
-Nitrophenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.24 (chloroform: methanol = 1
9: 1); NMR (d ₆ -DMSO): δ 10.47 (s, 1H), 8.77 (s, 1H),
8.49 (d, J = 8.1Hz, 1H), 8.30 (d, J = 8.7Hz, 2H),
8.08 (d, J = 8.7Hz, 2H), 4.61 (s, 2H), 4.20-4.07
(m, 1H), 3.58-3.38 (m, 10H), 3.23 (s, 3H), 2.47-2.
36 (m, 1H), 1.83-1.58 (m, 2H), 1.10 (t, J = 7.2Hz,
3H).

Example 49 (239) N-hydroxy-2 (R) -methoxymethyl-5- (2
-Methoxyethoxy) methoxy-4 (S)-[N- (4
-Cyanophenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.26 (chloroform: methanol = 1
9: 1); NMR (d ₆ -DMSO): δ 10.45 (s, 1H), 8.74 (s, 1H),
8.40 (d, J = 8.4Hz, 1H), 7.98 (d, J = 8.8Hz, 2H),
7.93 (d, J = 8.8Hz, 2H), 4.61 (s, 2H), 4.20-4.00
(m, 1H), 3.60-3.24 (m, 8H), 3.20 (s, 3H), 3.17 (s,
3H), 2.43-2.29 (m, 1H), 1.82-1.50 (m, 2H).

Example 49 (240) N-hydroxy-2 (R) -methoxymethyl-5-ethoxymethoxy-4 (S)-[N- (trans-4-methylcyclohexylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.27 (chloroform: methanol = 1
9: 1); NMR (d ₆ -DMSO): δ 10.41 (s, 1H), 8.75 (s, 1H),
7.43 (d, J = 8.7Hz, 1H), 4.56 (s, 2H), 3.86-3.72
(m, 1H), 3.47 (q, J = 7.2Hz, 2H), 3.41-3.20 (m, 4H),
3.15 (s, 3H), 2.36- 2.24 (m, 1H), 2.05-1.93 (m, 1
H), 1.77-1.56 (m, 5H), 1.49-1.18 (m, 4H), 1.10 (t,
J = 7.2Hz, 3H), 0.95- 0.77 (m, 5H).

Example 49 (241) N-hydroxy-2 (R) -methoxymethyl-5-ethoxymethoxy-4 (S)-[N- (4-bromophenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.31 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.43 (s, 1H), 8.74 (brs, 1
H), 8.21 (d, J = 8.4Hz, 1H), 7.78 (d, J = 8.7Hz, 2H),
7.66 (d, J = 8.7Hz, 2H), 4.58 (s, 2H), 4.13-4.01 (m,
1H), 3.50-3.31 (m, 6H), 3.16 (s, 3H), 2.42-2.12
(m, 1H), 1.79-1.53 (m, 2H), 1.07 (t, J = 7.2Hz, 3
H).

Example 49 (242) N-hydroxy-2 (R) -methoxymethyl-5-ethoxymethoxy-4 (S)-[N- (4-chlorophenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.31 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.44 (s, 1H), 8.74 (s, 1H),
8.21 (d, J = 8.4Hz, 1H), 7.76 (d, J = 8.7Hz, 2H), 7.5
2 (d, J = 8.7Hz, 2H), 4.58 (s, 2H), 4.16-4.02 (m, 1
H), 3.50-3.33 (m, 6H), 3.16 (s, 3H), 2.42-2.32 (m,
1H), 1.79-1.55 (m, 2H), 1.07 (t, J = 7.2Hz, 3H).

Example 49 (243) N-hydroxy-2 (R) -benzyloxymethyl-5
-(2-methoxyethoxy) methoxy-4 (S)-[N
-(4-cyanophenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.30 (methylene chloride: methanol = 1
9: 1); NMR (d ₆ -DMSO): δ 10.49 (d, J = 1.5 Hz, 1H), 8.
77 (d, J = 1.5Hz, 1H), 8.41 (d, J = 8.4Hz, 1H), 7.
98 (d, J = 8.7Hz, 2H), 7.94 (d, J = 8.7Hz, 2H), 7.2
9 (m, 5H), 4.60 (s, 2H), 4.45 (d, J = 12.0Hz, 1H),
4.39 (d, J = 12.0Hz, 1H), 4.10 (m, 1H), 3.60-3.36
(m, 8H), 3.18 (s, 3H), 2.45 (m, 1H), 1.78 (m, 1H),
1.63 (m, 1H).

Example 49 (244) N-hydroxy-2 (R) -benzyloxymethyl-5
-Ethoxymethoxy-4 (S)-[N- (4-chlorophenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.32 (methylene chloride: methanol = 1
9: 1); NMR (d ₆ -DMSO): δ 10.48 (s, 1H), 8.76 (s, 1H),
8.22 (d, J = 8.4Hz, 1H), 7.85 (d, J = 8.7Hz, 2H),
7.52 (d, J = 8.7Hz, 2H), 7.29 (m, 5H), 4.57 (s, 2
H), 4.44 (d, J = 12.0Hz, 1H), 4.39 (d, J = 12.0Hz,
1H), 4.08 (m, 1H), 3.55-3.40 (m, 6H), 2.45 (m, 1
H), 1.78 (m, 1H), 1.62 (m, 1H), 1.05 (t, J = 7.2Hz,
3H).

Example 49 (245) N-hydroxy-2 (R) -benzyloxymethyl-5
-Ethoxymethoxy-4 (S)-[N- (4-bromophenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.32 (methylene chloride: methanol = 1
9: 1); NMR (d ₆ -DMSO): δ 10.49 (d, J = 1.8 Hz, 1H), 8.
77 (d, J = 1.8Hz, 1H), 8.22 (d, J = 8.4Hz, 1H), 7.
78 (d, J = 8.7Hz, 2H), 7.66 (d, J = 8.7Hz, 2H), 7.2
9 (m, 5H), 4.57 (s, 2H), 4.44 (d, J = 12.0Hz, 1H),
4.39 (d, J = 12.0Hz, 1H), 4.08 (m, 1H), 3.55-3.40
(m, 6H), 2.45 (m, 1H), 1.78 (m, 1H), 1.62 (m, 1H),
1.05 (t, J = 7.2Hz, 3H).

Example 49 (246) N-hydroxy-2 (R)-[2- (3-methoxyphenoxy) ethyl] -5-ethoxymethoxy-4 (S)-
[N- (4-nitrophenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.40 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.50 (s, 1H), 8.76 (s, 1H),
8.48 (d, J = 8.4Hz, 1H), 8.30 (d, J = 8.6Hz, 2H), 8.0
6 (d, J = 8.6Hz, 2H), 7.13 (t, J = 8.3Hz, 1H), 6.52-6.3
5 (m, 3H), 4.59 (s, 2H), 4.25-4.12 (m, 1H), 3.95-
3.75 (m, 2H), 3.68 (s, 3H), 3.60-3.40 (m, 4H), 2.40
-2.25 (m, 1H), 2.00-1.65 (m, 4H), 1.07 (t, J = 7.1H
z, 3H).

Example 49 (247) N-hydroxy-2 (R) -methoxymethyl-5-ethoxymethoxy-4 (S)-[N-[(2-nitrothiophen-5-yl) carbonyl] amino] pentane Amide

Embedded image TLC: Rf 0.37 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.46 (s, 1H), 8.75 (brs, 1
H), 8.71 (d, J = 8.4Hz, 1H), 8.13 (d, J = 4.2Hz, 1H),
7.82 (d, J = 4.2Hz, 1H), 4.58 (s, 2H), 3.97-4.09 (m,
1H), 3.50-3.38 (m, 6H), 3.17 (s, 3H), 2.41-2.32
(m, 1H), 1.79-1.55 (m, 2H), 1.07 (t, J = 7.2Hz, 3
H).

Example 49 (248) N-hydroxy-2 (R) -methoxymethyl-5-ethoxymethoxy-4 (S)-[N-[(2-bromothiophen-5-yl) carbonyl] amino] pentane Amide

Embedded image TLC: Rf 0.34 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.44 (s, 1H), 8.75 (s, 1H),
8.27 (d, J = 8.1Hz, 1H), 7.61 (d, J = 4.2Hz, 1H), 7.2
7 (d, J = 4.2Hz, 1H), 4.57 (s, 2H), 4.05-3.91 (m, 1
H), 3.50-3.37 (m, 6H), 3.16 (s, 3H), 2.41-2.31 (m,
1H), 1.78-1.51 (m, 2H), 1.07 (t, J = 7.2Hz, 3H).

Example 49 (249) N-hydroxy-2 (R)-(2-methoxyethoxy)
Methyl-5-ethoxymethoxy-4 (S)-[N- (4
-Bromophenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.31 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.43 (s, 1H), 8.74 (s, 1H),
8.20 (d, J = 8.6Hz, 1H), 7.78 (d, J = 8.6Hz, 2H), 7.6
5 (d, J = 8.6Hz, 2H), 4.58 (s, 2H), 4.18-4.01 (m, 1
H), 3.50-3.36 (m, 10H), 3.20 (s, 3H), 2.44-2.39
(m, 1H), 1.81-1.52 (m, 2H), 1.07 (t, J = 7.0Hz, 3
H).

Example 49 (250) N-hydroxy-2 (R)-(2-methoxyethoxy)
Methyl-5- (2-methoxyethoxy) methoxy-4
(S)-[N- (4-cyanophenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.24 (chloroform: methanol = 1
9: 1); NMR (d ₆ -DMSO): δ 10.45 (brs, 1H), 8.78 (brs,
1H), 8.43 (d, J = 8.1Hz, 1H), 7.99 (d, J = 8.4Hz, 2H),
7.94 (d, J = 8.4Hz, 2H), 4.61 (s, 2H), 4.16-4.02
(m, 1H), 3.57-3.35 (m, 12H), 3.21 (s, 3H), 3.20
(s, 3H), 2.42-2.32 (m, 1H), 1.80-1.56 (m, 2H).

Example 49 (251) N-hydroxy-2 (R)-(2-methoxyethoxy)
Methyl-5-ethoxymethoxy-4 (S)-[N- (4
-Chlorophenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.34 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.43 (s, 1H), 8.74 (brs, 1
H), 8.20 (d, J = 8.4Hz, 1H), 7.87-7.83 (m, 2H), 7.54-
7.49 (m, 2H) 4.58 (s, 2H), 4.18-4.10 (m, 1H), 3.52
-3.36 (m, 10H), 3.20 (s, 3H), 2.42-2.29 (m, 1H),
1.81-1.53 (m, 2H), 1.07 (t, J = 7.0Hz, 3H).

Example 49 (252) N-hydroxy-2 (R) -benzyloxymethyl-5
-Ethoxymethoxy-4 (S)-[N- (trans-4
-Methylcyclohexylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.34 (chloroform: methanol = 1
9: 1); NMR (d ₆ -DMSO): δ 10.46 (s, 1H), 8.78 (s, 1H),
7.44 (d, J = 8.4Hz, 1H), 7.38-7.21 (m, 5H), 4.59-4.
52 (m, 2H), 4.43 (d, J = 12.0Hz, 1H), 4.37 (d, J = 12.
0Hz, 1H), 3.85-3.72 (m, 1H), 3.54-3.28 (m, 6H), 2.
43-2.30 (m, 1H), 2.06-1.92 (m, 1H), 1.76-1.59 (m, 5
H), 1.52-1.20 (m, 4H), 1.09 (t, J = 6.9Hz, 3H), 0.93-
0.75 (m, 5H).

Example 49 (253) N-hydroxy-2 (R)-(3-thienyl) methoxymethyl-5-ethoxymethoxy-4 (S)-[N- (4
-Nitrophenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.34 (chloroform: methanol = 1
9: 1); NMR (d ₆ -DMSO): δ 10.49 (s, 1H), 8.76 (s, 1H),
8.49 (d, J = 8.4Hz, 1H), 8.30 (d, J = 8.8Hz, 2H), 8.0
6 (d, J = 8.8Hz, 2H), 7.49 (dd, J = 5.2, 2.8Hz, 1H),
7.40-7.36 (m, 1H), 7.03 (dd, J = 5.2, 1.6Hz, 1H), 4.
59 (s, 2H), 4.50-4.36 (m, 2H), 4.21-4.00 (m, 1H),
3.60-3.36 (m, 6H), 2.52-2.38 (m, 1H), 1.88-1.56 (m,
2H), 1.07 (t, J = 7.0Hz, 3H).

Examples 49 (254) to 49 (263) Using the corresponding compound in place of the compound prepared in Reference Example 4, Example 37 → Example 39 → Example 45 → Example 46 (benzyl bromide) The corresponding compound was used in place of the above.) → Example 47 → Example 48 → Operation was performed in the same manner as shown in Example 49 to obtain the compound shown below.

Example 49 (254) N-hydroxy-2 (R)-(2-pyridinyl) methyl-5-hydroxy-4 (S)-[N- (4-phenoxyphenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.17 (chloroform: methanol: acetic acid: water = 100: 10: 1: 1); NMR (d ₆ -DMSO): δ 10.35 (1H, brs), 8.63 (1H, br)
s), 8.42-8.40 (1H, m), 7.91-7.86 (3H, m), 7.64 (1H, d
t, J = 7.8Hz, 1.8Hz), 7.45-7.39 (2H, m), 7.25-7.14 (3
H, m), 7.07-7.00 (4H, m), 4.67 (1H, brs), 4.15-3.94
(1H, m), 3.50-3.34 (2H, m), 2.97-2.81 (2H, m), 2.71-
2.62 (1H, m), 1.82-1.65 (2H, m).

Example 49 (255) N-hydroxy-2 (S) -methyl-5-hydroxy-
4 (S)-[N- (4-phenoxyphenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.14 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.33 (1H, s), 8.62 (1H, s),
7.89-7.83 (3H, m), 7.41 (2H, t, J = 7.6Hz), 7.17 (1H
, t, J = 7.6Hz), 7.04 (2H, d, J = 7.6Hz), 7.00 (2H,
d, J = 8.7Hz), 4.68 (1H, t, J = 5.7Hz), 4.02-3.91 (1H,
m), 3.45-3.28 (2H, m), 2.21-2.08 (1H, m), 1.72-
1.55 (2H, m), 0.98 (3H, d, J = 6.6Hz).

Example 49 (256) N-hydroxy-2 (S) -methyl-5-hydroxy-
4 (S)-[N- (4-bromophenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.25 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.37 (s, 1H), 8.64 (s, 1H),
8.02 (d, J = 8.6Hz, 1H), 7.81 (d, J = 8.4Hz, 2H), 7.6
5 (d, J = 8.4Hz, 2H), 4.80-4.64 (m, 1H), 4.10-3.88
(m, 1H), 3.60-3.10 (m, 2H), 2.26-2.06 (m, 1H), 1.
80-1.56 (m, 2H), 1.02 (d, J = 6.8Hz, 3H).

Example 49 (257) N-hydroxy-2 (S)-(3-methoxybenzyl)
-5-hydroxy-4 (S)-[N- (4-bromophenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.45 (methylene chloride: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.28 (s, 1H), 8.63 (s, 1H),
8.04 (brd, J = 8.4Hz, 1H), 7.82 (d, J = 8.4Hz, 2H), 7.
66 (d, J = 8.4Hz, 2H), 7.11 (t, J = 8.0Hz, 1H), 6.67
(m, 3H), 4.69 (brt, J = 5.8Hz, 1H), 4.09 (m, 1H), 3.
65 (s, 3H), 3.44 (m, 2H), 2.75 (brd, J = 7.2Hz, 2H),
2.33 (m, 1H), 1.85-1.50 (m, 2H).

Example 49 (258) N-hydroxy-2 (S)-(3-methoxybenzyl)
-5-hydroxy-4 (S)-[N- (4-nitrophenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.52 (methylene chloride: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.31 (s, 1H), 8.64 (s, 1H),
8.34 (brd, J = 8.4Hz, 1H), 8.30 (d, J = 9.2Hz, 2H), 8.
09 (d, J = 9.2Hz, 2H), 7.11 (t, J = 8.8Hz, 1H), 6.70
(m, 3H), 4.73 (brt, J = 5.8Hz, 1H), 4.10 (m, 1H), 3.
67 (s, 3H), 3.43 (m, 2H), 2.73 (brd, J = 7.0Hz, 2H),
2.35 (m, 1H), 1.85-1.55 (m, 2H).

Example 49 (259) N-hydroxy-2 (S)-(3-methoxybenzyl)
-5-hydroxy-4 (S)-[N- (4-chlorophenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.52 (methylene chloride: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.28 (s, 1H), 8.63 (s, 1H),
8.06 (brd, J = 8.4Hz, 1H), 7.89 (d, J = 8.7Hz, 2H), 7.
52 (d, J = 8.7Hz, 2H), 7.11 (t, J = 8.4Hz, 1H), 6.67
(m, 3H), 4.70 (brt, J = 5.7Hz, 1H), 4.10 (m, 1H), 3.
65 (s, 3H), 3.41 (m, 2H), 2.72 (brd, J = 7.2Hz, 2H),
2.33 (m, 1H), 1.82-1.55 (m, 2H).

Example 49 (260) N-hydroxy-2 (S)-(3-methoxybenzyl)
-5-hydroxy-4 (S)-[N-[(2-bromothiophen-5-yl) carbonyl] amino] pentanamide

Embedded image TLC: Rf 0.52 (methylene chloride: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.30 (s, 1H), 8.64 (s, 1H),
8.13 (brd, J = 8.8Hz, 1H), 7.63 (d, J = 4.0Hz, 1H), 7.
27 (d, J = 4.0Hz, 1H), 7.12 (t, J = 8.4Hz, 1H), 6.69
(m, 3H), 4.72 (brs, 1H), 4.00 (m, 1H), 3.68 (s, 3
H), 3.39 (m, 2H), 2.71 (brd, J = 7.2Hz, 2H), 2.32
(m, 1H), 1.83-1.49 (m, 2H).

Example 49 (261) N-hydroxy-2 (S)-(3-methoxybenzyl)
-5-hydroxy-4 (S)-[N-[(2-nitrothiophen-5-yl) carbonyl] amino] pentanamide

Embedded image TLC: Rf 0.47 (methylene chloride: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.32 (s, 1H), 8.65 (s, 1H),
8.57 (brd, J = 9.0Hz, 1H), 8.14 (d, J = 4.5Hz, 1H), 7.
84 (d, J = 4.5Hz, 1H), 7.12 (t, J = 8.4Hz, 1H), 6.69
(m, 3H), 4.78 (brs, 1H), 4.01 (m, 1H), 3.69 (s, 3
H), 3.42 (m, 2H), 2.71 (m, 2H), 2.33 (m, 1H), 1.81
-1.54 (m, 2H).

Example 49 (262) N-hydroxy-2 (S)-(3-methoxybenzyl)
-5-hydroxy-4 (S)-[N- (4-cyanophenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.39 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.31 (s, 1H), 8.64 (s, 1H),
8.23 (d, J = 8.8Hz, 1H), 8.03 (d, J = 8.4Hz, 2H), 7.9
3 (d, J = 8.4Hz, 2H), 7.18-7.06 (m, 1H), 6.75-6.64
(m, 3H), 4.71 (t, J = 5.8Hz, 1H), 4.21-4.00 (m, 1H),
3.67 (s, 3H), 3.57-3.37 (m, 2H), 2.74 (d, J = 7.0Hz,
2H), 2.42- 2.25 (m, 1H), 1.90-1.52 (m, 2H).

Example 49 (263) N-hydroxy-2 (R) -benzyloxymethyl-5
-Hydroxy-4 (S)-[N- (4-nitrophenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.62 (methylene chloride: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.47 (s, 1H), 8.74 (s, 1H),
8.33 (d, J = 8.8Hz, 1H), 8.29 (d, J = 8.6Hz, 2H),
8.06 (d, J = 8.6Hz, 2H), 7.29 (m, 5H), 4.72 (t, J
= 5.6Hz, 1H), 4.45 (d, J = 12.4Hz, 1H), 4.38 (d, J
= 12.0Hz, 1H), 3.95 (m, 1H), 3.60-3.35 (m, 4H),
2.45 (m, 1H), 1.78 (m, 1H), 1.62 (m, 1H).

Using the compounds corresponding to Examples 49 (264) to 49 (269) , Example 37 → Example 39 → Example 41 (in some cases, the corresponding compound may be used instead of methoxymethyl chloride) → Example 43 (using a corresponding compound instead of benzyl bromide) → Example 5 → Example 44 → The same procedure as shown in Example 49 was performed to obtain the compound shown below.

Example 49 (264) N-hydroxy-5-methoxymethoxy-4 (S)-
[N-methyl-N- [4- (4-chlorophenyl) phenylcarbonyl] amino] pentanamide

Embedded image TLC: Rf 0.22 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.36 (1H, s), 7.75-7.65 (4
H, m), 7.54-7.37 (4H, m), 4.66-3.68 (3H, m), 3.64-
3.35 (2H, m), 3.25, 3.21 (3H, s), 2.81, 2.74 (3H,
s), 2.07-1.55 (4H, m).

Example 49 (265) N-hydroxy-2 (S)-(3-pyridyl) methyl-
5-methoxymethoxy-4 (S)-[N-methyl-N-
[4- (4-chlorophenyl) phenylcarbonyl] amino] pentanamide

Embedded image TLC: Rf 0.42 (chloroform: methanol: acetic acid = 9: 1: 0.5); NMR (d ₆ -DMSO): δ 10.43 (1H, s), 8.72 (1H, s),
8.45-8.29 (2H, m), 7.78-7.60 (5H, m), 7.58-7.40 (4
H, m), 7.33- 7.22 (1H, m), 4.97-4.84 (0.6H, m), 4.
56-4.44 (2H, m), 3.94-3.84 (0.4H, m), 3.64-3.30 (2
H, m), 3.25,3.20 (3H, s), 2.82, 2.73 (3H, s), 2.85
-2.21 (3H, m), 1.88-1.49 (2H, m).

Example 49 (266) N-hydroxy-2 (S) -methyl-5-ethoxymethoxy-4 (S)-[N-methyl-N- (4-bromophenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.36 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.47 & 10.45 (s, 1H), 8.72 & 8.
69 (s, 1H), 7.63 & 7.60 (d, J = 8.4Hz, 2H), 7.32 & 7.30
(d, J = 8.4Hz, 2H), 4.79-4.67 & 3.77-3.64 (m, 1H), 4.6
1 & 4.56 (s, 2H), 3.60-3.36 (m, 4H), 2.78 & 2.65 (s,
3H), 2.18-2.06 & 2.03-1.92 (m, 1H), 1.85-1.67 (m, 1
H), 1.54-1.43 & 1.38-1.27 (m, 1H), 1.10 (q, J = 6.6Hz,
3H), 1.03 & 0.73 (d, J = 6.9Hz, 3H).

Example 49 (267) N-hydroxy-2 (S)-(3-methoxybenzyl)
-5-ethoxymethoxy-4 (S)-[N-methyl-N
-(4-Bromophenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.47 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.44 & 10.42 (s, 1H), 8.71
(s, 1H), 7.66 & 7.53 (d, J = 8.1Hz, 2H), 7.36 & 7.29 (d,
J = 8.1Hz, 2H), 7.14 (t, J = 8.0Hz, 1H), 6.80-6.58 (m,
3H), 4.89-4.79 & 3.75-3.63 (m, 1H), 4.60 & 4.5 2 (s,
2H), 3.71 & 3.67 (s, 3H), 3.58-3.36 (m, 4H), 2.78 & 2.6
8 (s, 3H), 2.77-2.56 (m, 2H), 2.33-2.15 (m, 1H),
1.85-1.72 (m, 1H), 1.66-1.57 & 1.54-1.43 (m, 1H), 1.
15-1.04 (m, 3H).

Example 49 (268) N-hydroxy-2 (S) -methyl-5-ethoxymethoxy-4 (S)-[N-methyl-N- (4-nitrophenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.27 (chloroform: methanol = 1
9: 1); NMR (d ₆ -DMSO): δ 10.51 and 10.45 (s, 1H), 8.7
6 and 8.70 (s, 1H), 8.29 and 8.26 (d, J = 8.8Hz, 2H),
7.64 and 7.60 (d, J = 8.8Hz, 2H), 4.86-4.51 (m, 3
H), 3.70-3.36 (m, 4H), 2.84 and 2.65 (s, 3H), 2.22
-1.65 (m, 2H), 1.60-1.20 (m, 1H), 1.15 and 1.12 (t,
J = 7.0Hz, 3H), 1.07 and 0.79 (d, J = 7.0Hz, 3H).

Example 49 (269) N-hydroxy-2 (S) -methyl-5-benzyloxymethoxy-4 (S)-[N-methyl-N- (4-nitrophenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.43 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.50 & 10.43 (s, 1H), 8.75 & 8.
69 (d, J = 1.5Hz, 1H), 8.27 & 8.25 (d, J = 8.9Hz, 2H), 7.
63 & 7.60 (d, J = 8.9Hz, 2H), 7.37-7.26 (m, 5H), 4.83-
4.67 (m, 2.5H), 4.58-4.46 (m, 2H), 3.69-3.56 & 3.48
-3.37 (m, 2.5H), 2.83 & 2.63 (s, 3H), 2.20-2.10 & 2.
06-1.95 (m, 1H), 1.90-1.72 (m, 1H), 1.55-1.44 & 1.39
-1.29 (m, 1H), 1.05 & 0.76 (d, J = 6.8Hz, 3H).

Examples 49 (270) to 49 (277) Example 3 was repeated using the corresponding compound in place of Reference Example 4.
7 → Example 39 → Example 45 → Example 46 (using the corresponding compound in place of benzyl bromide) → Example 5 →
By operating in the same manner as in Example 47 → Example 48 → Example 49, the following compounds were obtained.

Example 49 (270) N-hydroxy-2 (S)-(3-methoxybenzyl)
-5-hydroxy-4 (S)-[N-methyl-N- (4
-Chlorophenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.51 (methylene chloride: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.40 (s, 0.45H), 10.38 (s,
0.55H), 8.67 (s, 1H), 7.53-7.35 (m, 3.45H), 7.24-
7.10 (m, 1.55H), 6.73-6.56 (m, 3H), 4.94 (brt, J =
5.2Hz, 0.45H), 4.79 (brt, J = 5.2Hz, 0.55H), 4.72
(m, 0.55H), 3.70 (s, 1.65H), 3.67 (s, 1.35H), 3.70
-3.30 (m, 2.45H), 2.78 (s, 1.35H), 2.66 (s, 1.65H),
2.80-2.10 (m, 4H), 1.80-1.35 (m, 2H).

Example 49 (271) N-hydroxy-2 (S)-(3-methoxybenzyl)
-5-hydroxy-4 (S)-[N-methyl-N- (4
-Nitrophenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.56 (methylene chloride: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.39 (s, 0.5H), 10.37 (s,
0.5H), 8.69 (s, 0.5H), 8.64 (s, 0.5H), 8.28 (d, J =
8.8Hz, 1H), 8.17 (d, J = 8.8Hz, 1H), 7.68 (d, J = 8.8H
z, 1H), 7.59 (d, J = 8.8Hz, 1H), 7.11 (m, 1H), 6.72
(m, 2H), 6.57 (m, 1H), 4.95 (brt, J = 5.2Hz, 0.5H),
4.82 (brt, J = 5.2Hz, 0.5H), 4.69 (m, 0.5H), 3.68
(s, 3H), 3.60-3.30 (m, 2.5H), 3.55-3.25 (m, 2H),
2.80 (s, 1.5H), 2.63 (s, 1.5H), 2.80-2.10 (m, 4H),
1.80-1.35 (m, 2H).

Example 49 (272) N-hydroxy-2 (S)-(3-methoxybenzyl)
-5-hydroxy-4 (S)-[N-methyl-N- (4
-Bromophenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.45 (methylene chloride: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.41 (s, 0.45H), 10.38 (s,
0.55H), 8.67 (s, 1H), 7.64 (d, J = 8.4Hz, 1.1H), 7.5
3 (d, J = 8.4Hz, 0.9H), 7.39 (d, J = 8.4Hz, 1.1H), 7.3
5 (d, J = 8.4Hz, 0.9H), 7.13 (t, J = 7.8Hz, 1H), 6.70
(m, 2.1H), 6.57 (m, 0.9H), 4.94 (brt, J = 5.1Hz, 0.4
5H), 4.79 (brt, J = 5.7Hz, 0.55H), 4.70 (m, 0.55H),
3.70 (s, 1.65H), 3.67 (s, 1.35H), 3.70-3.60 (m, 0.
45H), 3.55-3.25 (m, 2H), 2.78 (s, 1.35H), 2.66 (s,
1.65H), 2.80-2.10 (m, 4H), 1.80-1.35 (m, 2H).

Example 49 (273) N-hydroxy-2 (S) -methyl-5-hydroxy-
4 (S)-[N-methyl-N- (4-nitrophenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.16 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.49 & 10.42 (s, 1H), 8.72 & 8.
67 (d, J = 1.5Hz, 1H), 8.27 & 8.25 (d, J = 8.8Hz, 2H), 7.
65 & 7.62 (d, J = 8.8Hz, 2H), 5.01 & 4.83 (t, J = 5.4Hz, 1
H), 4.65-4.54 & 3.51-3.40 (m, 1H), 3.53-3.27 (m, 2
H), 2.81 & 2.62 (s, 3H), 2.17-2.09 & 2.03-1.91 (m, 1
H), 1.80-1.63 (m, 1H), 1.52-1.42 & 1.33-1.22 (m, 1
H), 1.05 & 0.72 (d, J = 6.9Hz, 3H).

Example 49 (274) N-hydroxy-2 (S) -benzyl-5-hydroxy-4 (S)-[N-methyl-N- (4-nitrophenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.25 (chloroform: methanol: water =
NMR (d ₆ -DMSO): δ 10.40 and 10.37 (s, 1H), 8.7
0 and 8.65 (brs, 1H), 8.29 and 8.19 (d, J = 8.7Hz, 2
H), 7.69 and 7.60 (d, J = 8.7Hz, 2H), 7.30-7.01 (m,
5H), 4.91 and 4.84 (t, J = 5.4Hz, 1H), 4.75-4.64 and
3.54-3.44 (m, 1H), 3.49-3.25 (m, 2H), 2.81 and 2.6
5 (s, 3H), 2.84-2.51 (m, 2H), 2.35-2.12 (m, 1H),
1.84-1.56 and 1.47-1.36 (m, 2H).

Example 49 (275) N-hydroxy-2 (S) -methyl-5-hydroxy-
4 (S)-[N-methyl-N- (4-bromophenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.17 (chloroform: methanol: water =
9: 1: 0.1); NMR (d ₆ -DMSO): δ 10.43 (s, 1H), 8.66 (s, 1H),
7.62 and 7.59 (d, J = 8.1Hz, 2H), 7.35 (d, J = 8.1Hz,
2H), 4.98-4.92 and 4.81-4.73 (m, 1H), 4.63-4.52 a
nd 3.64-3.52 (m, 1H), 3.52-3.39 (m, 2H), 2.77 and
2.64 (s, 3H), 2.15-2.05 and 2.00-1.89 (m, 1H), 1.77
-1.58 and 1.53-1.43 and 1.32-1.21 (m, 2H), 1.04 an
d 0.68 (d, J = 6.7Hz, 3H).

Example 49 (276) N-hydroxy-2 (S) -benzyl-5-hydroxy-4 (S)-[N-methyl-N- (4-bromophenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.25 (chloroform: methanol: water =
9: 1: 0.1); NMR (d ₆ -DMSO): δ 10.40 and 10.37 (s, 1H), 8.6
6 (s, 1H), 7.64 and 7.54 (d, J = 8.6Hz, 2H), 7.39 and
7.36 (d, J = 8.6Hz, 2H), 7.28-6.97 (m, 5H), 4.95 an
d 4.79 (t, J = 5.4Hz, 1H), 4.75-4.65 and 3.69-3.60
(m, 1H), 3.52-3.26 (m, 2H), 2.78 and 2.66 (s, 3H),
2.82-2.55 (m, 2H), 2.31-2.12 (m, 1H), 1.80-1.56 a
nd 1.67-1.35 (m, 2H).

Example 49 (277) N-hydroxy-2 (S) -methyl-5-hydroxy-
4 (S)-[N-methyl-N- (4-chlorophenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.17 (chloroform: methanol: water =
9: 1: 0.1); NMR (d ₆ -DMSO): δ 10.45 and 10.43 (s, 1H), 8.6
9 and 8.66 (s, 1H), 7.53-7.38 (m, 4H), 4.96 and 4.7
7 (t, J = 5.3Hz, 1H), 4.63-4.52 and 3.65-3.51 (m, 1
H), 3.51-3.40 (m, 2H), 2.78 and 2.64 (s, 3H), 2.15
-2.05 and 1.98-1.88 (m, 1H), 1.77-1.54 (m, 1H), 1.
54-1.43 and 1.32-1.21 (m, 1H), 1.03and 0.67 (d, J =
6.8Hz, 3H).

Example 50 2 (S) -benzyloxy-3 (S) -hydroxy-4
-(N- (4- (3-methoxy-1-propynyl) phenylcarbonyl) amino) butanoic acid ethyl ester

Embedded image 2 (S) instead of 4-aminobutanoic acid ethyl ester
-Benzyloxy-3 (S) -hydroxy-4-aminobutanoic acid ethyl ester (Bioorg. Med. Chem. Lett.,
2 , 515 (1992). )
And using the corresponding acid halide in place of the compound produced in Reference Example 4 and in the same manner as in the method shown in Example 1, to obtain the title compound having the following physical data. TLC: Rf 0.20 (n-hexane: ethyl acetate = 3:
2).

Example 51 2 (S) -Benzyloxy-3 (S) -hydroxy-4
-(N- (4- (3-methoxy-1-propynyl) phenylcarbonyl) amino) butanoic acid

Embedded image Using the compound prepared in Example 50 in place of the compound prepared in Example 1, and operating in the same manner as in the method shown in Example 2, the title compound having the following physical data was obtained. TLC: Rf 0.22 (chloroform: methanol = 9:
1).

Example 52 2 (S) -benzyloxy-3 (S) -tert-butylcarbonyloxy-4- (N- (4- (3-methoxy-1-
Propynyl) phenylcarbonyl) amino) butanoic acid ethyl ester

Embedded image Example 5 instead of ethyl 4-aminobutanoate
0, using the compound prepared in Example 1 (using pivaloyl chloride instead of the compound prepared in Reference Example 4), to give the title compound having the following physical data. Obtained. TLC: Rf 0.44 (n-hexane: ethyl acetate = 7:
3); NMR (CDCl ₃ ): δ 7.49 (2H, d, J = 8.8 Hz), 7.43-
7.30 (7H, m), 6.80-6.68 (1H, m), 5.36 (1H, td, J =
5.6, 3.8Hz), 4.87 (1H, d, J = 11.4Hz), 4.43 (1H, d,
J = 11.4Hz), 4.34 (2H, s), 4.25 (1H, d, J = 3.8Hz), 4.
22 (2H, q, J = 7.0Hz), 3.90 (1H, dt, J = 14.2, 5.6Hz),
3.66 (1H, dt, J = 14.2, 5.6Hz), 3.46 (3H, s), 1.29
(3H, t, J = 7.0Hz), 1.14 (9H, s).

Example 53 2-Benzyloxy-4- (N- (4- (3-methoxy-1-propynyl) phenylcarbonyl) amino) -2
-Butenoic acid

Embedded image Using the compound prepared in Example 52 instead of the compound prepared in Example 1, and operating in the same manner as in the method shown in Example 2, the title compound having the following physical data was obtained. TLC: Rf 0.36 (chloroform: methanol = 9:
1).

Example 54 N-hydroxy-2 (S) -benzyloxy-3 (S)
-Hydroxy-4- (N- (4- (3-methoxy-1-
Propynyl) phenylcarbonyl) amino) butyramide

Embedded image Using the compound prepared in Example 51 in place of the compound prepared in Example 2, and operating in the same manner as in the method shown in Example 3 → Example 4, the title compound having the following physical data was obtained. TLC: Rf 0.25 (chloroform: methanol = 9:
1); NMR (CD ₃ OD): δ 7.74 (2H, d, J = 8.4 Hz), 7.49
(2H, d, J = 8.4Hz), 7.45-7.20 (5H, m), 4.73 (1H, d,
J = 11.4Hz), 4.49 (1H, d, J = 11.4Hz), 4.34 (2H, s),
4.14-3.95 (1H, m), 3.91 (1H, d, J = 3.4Hz), 3.60 (1
H, dd, J = 13.6, 5.4Hz), 3.44 (3H, s), 3.42 (1H, dd,
J = 13.6, 7.2Hz).

Example 54 (1) N-hydroxy-2-benzyloxy-4- (N- (4
-(3-methoxy-1-propynyl) phenylcarbonyl) amino) -2-butenamide

Embedded image Using the compound prepared in Example 53 instead of the compound prepared in Example 51, and operating in the same manner as in the method shown in Example 54, the title compound having the following physical data was obtained. TLC: Rf 0.37 (chloroform: methanol = 9:
1); NMR (CD ₃ OD): δ 8.52-8.40 (1H, m), 7.74 (2H,
d, J = 8.4Hz), 7.49 (2H, d, J = 8.4Hz), 7.45-7.20 (5H,
m), 5.89 (1H, t, J = 6.6Hz), 4.88 (2H, s), 4.33 (2H,
s), 4.02-3.90 (2H, m), 3.43 (3H, s).

Example 55 cis-1-carboxymethyl-2- (N- (4- (3-
Methoxy-1-propynyl) phenylcarbonyl) amino) cyclopentane

Embedded image Cis-1 instead of 4-aminobutanoic acid ethyl ester
-Carboxymethyl-2-aminocyclopentane (J. C.
hem. Soc., PerkinTrans. 1, 11 , 2553 (1982)) using the corresponding acid halide in place of the compound prepared in Reference Example 4 and the method shown in Example 1. By the same operation, the title compound having the following physical properties was obtained. TLC: Rf 0.80 (chloroform: methanol: acetic acid = 18: 2: 1).

Example 55 (1) -55 (4) trans-1-carboxymethyl-2-aminocyclopentane, cis-3-aminocyclopentanoic acid instead of cis-1-carboxymethyl-2-aminocyclopentane , Trans-3-aminocyclopentanoic acid (Chem. Be
r., 101 , 1525 (1968)) and 2-
The following compound was obtained in the same manner as in Example 55 using aminomethylcyclopentanoic acid to obtain the following compound.

Example 55 (1) trans-1-carboxymethyl-2- (N- (4-
(3-methoxy-1-propynyl) phenylcarbonyl) amino) cyclopentane

Embedded image TLC: Rf 0.36 (chloroform: methanol = 1
0: 1); NMR (CDCl ₃ ): δ 7.72 (2H, d, J = 8.4 Hz), 7.49
(2H, d, J = 8.4Hz), 6.49 (1H, d, J = 7.4Hz), 4.34 (2H,
s), 4.04 (1H, m), 3.46 (3H, s), 2.56 (2H, m), 2.25
(2H, m), 1.99 (1H, m), 1.75 (2H, m), 1.50 (2H, m
m).

Example 55 (2) trans-3- (N- (4- (3-methoxy-1-propynyl) phenylcarbonyl) amino) cyclopentanoic acid

Embedded image TLC: Rf 0.21 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 12.09 (1H, s), 8.40 (1H, d,
J = 6.8Hz), 7.85 (2H, d, J = 8.4Hz), 7.53 (2H, d, J = 8.
4Hz), 4.42-4.22 (3H, m), 3.34 (3H, s), 3.30-2.82
(1H, m), 2.20-1.48 (6H, m).

Example 55 (3) cis-3- (N- (4- (3-methoxy-1-propynyl) phenylcarbonyl) amino) cyclopentanoic acid

Embedded image TLC: Rf 0.32 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 12.11 (1H, s), 8.45 (1H, d,
J = 7.4Hz), 7.85 (2H, d, J = 8.8Hz), 7.52 (2H, d, J = 8.
8Hz), 4.34 (2H, s), 4.33-4.18 (1H, m), 3.34 (3H,
s), 2.84-2.66 (1H, m), 2.18 (1H, m), 2.00-1.50 (5
H, m).

Example 55 (4) trans-2- (N- (4- (3-methoxy-1-propynyl) phenylcarbonyl) aminomethyl) cyclopentanoic acid

Embedded image TLC: Rf 0.26 (chloroform: methanol = 1
9: 1); NMR (CDCl ₃ ): δ 7.72 (2H, d, J = 8.2 Hz), 7.46
(2H, d, J = 8.2Hz), 7.08-6.98 (1H, m), 4.33 (2H, s),
3.69 (1H, dt, J = 13.8, 5.4Hz), 3.45 (3H, s), 3.34
(1H, ddd, J = 13.8, 8.8, 5.4Hz), 2.62-2.30 (2H, m),
2.06-1.84 (3H, m), 1.80-1.62 (2H, m), 1.52-1.32 (1
H, m).

Example 56 cis-1- (N-hydroxyaminocarbonylmethyl)
-2- (N- (4- (3-methoxy-1-propynyl))
Phenylcarbonyl) amino) cyclopentane

Embedded image Using the compound prepared in Example 55 in place of the compound prepared in Example 2, and operating in the same manner as in the method shown in Example 3 → Example 4, the title compound having the following physical data was obtained. TLC: Rf 0.33 (chloroform: methanol = 1
0: 1); NMR (d ₆ -DMSO): δ 10.40 (1H, s), 8.37 (1H, d,
J = 7.8Hz), 7.86 (2H, d, J = 8.4Hz), 7.54 (2H, d, J = 8.
4Hz), 4.38 (1H, m), 4.35 (2H, s), 3.35 (3H, s), 2.
35 (1H, m), 2.09 (1H, dd, J = 14.6, 4.6Hz), 1.91 (1
H, m), 1.83 (1H, m), 1.80-1.50 (4H, m), 1.44 (1H,
m).

Examples 56 (1) to 56 (4) Example 55 was repeated in place of the compound prepared in Example 55.
Example 56 was prepared using the compounds prepared in (1) to (4).
The following operation was performed to obtain the compound shown below.

Example 56 (1) trans-1- (N-hydroxyaminocarbonylmethyl) -2- (N- (4- (3-methoxy-1-propynyl) phenylcarbonyl) amino) cyclopentane

Embedded image TLC: Rf 0.43 (chloroform: methanol = 1
0: 1); NMR (d ₆ -DMSO): δ 10.37 (1H, s), 8.41 (1H, d,
J = 8.0Hz), 7.87 (2H, d, J = 8.4Hz), 7.53 (2H, d, J = 8.
4Hz), 4.35 (2H, s), 3.90 (1H, m), 3.35 (3H, s), 2.
19 (2H, m), 1.87 (3H, m), 1.58 (3H, m,), 1.24 (1
H, m).

Example 56 (2) trans-1- (N-hydroxyaminocarbonyl)-
3- (N- (4- (3-methoxy-1-propynyl) phenylcarbonyl) amino) cyclopentane

Embedded image TLC: Rf 0.26 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.42 (1H, s), 8.80-8.60 (1
H, br), 8.37 (1H, d, J = 7.0Hz), 7.85 (2H, d, J = 8.4H
z), 7.53 (2H, d, J = 8.4Hz), 4.44-4.24 (3H, m), 3.35
(3H, s), 2.78-2.68 (1H, m), 2.10-1.50 (6H, m).

Example 56 (3) cis-1- (N-hydroxyaminocarbonyl) -3-
(N- (4- (3-methoxy-1-propynyl) phenylcarbonyl) amino) cyclopentane

Embedded image TLC: Rf 0.38 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.62 (1H, s), 8.94-8.76 (1
H, br), 8.82 (1H, d, J = 7.8Hz), 7.87 (2H, d, J = 8.4H
z), 7.53 (2H, d, J = 8.4Hz), 4.34 (2H, s), 4.42-4.22
(1H, m), 3.35 (3H, s), 2.70-2.55 (1H, m), 2.14-1.
95 (1H, m), 1.92-1.62 (5H, m).

Example 56 (4) trans-1- (N-hydroxyaminocarbonyl)-
2- (N- (4- (3-methoxy-1-propynyl) phenylcarbonyl) aminomethyl) cyclopentane

Embedded image TLC: Rf 0.31 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.39 (1H, s), 8.50 (1H, t,
J = 5.6Hz), 7.83 (2H, d, J = 8.2Hz), 7.52 (2H, d, J = 8.
2Hz), 4.34 (2H, s), 3.35 (3H, s), 3.32-3.14 (2H,
m), 2.40-2.22 (1H, m), 2.20-2.04 (1H, m), 1.90-1.5
0 (5H, m), 1.48-1.24 (1H, m).

Example 57 2 (R) -allyl-5-ethoxymethoxy-4 (S)-
[N- (4-phenoxyphenylcarbonyl) amino]
Pentanoic acid

Embedded image Example 37 → Example 39 → Example 41 (methoxy) in a solution of lithium diisopropylamide (3.6 ml) in tetrahydrofuran (20 ml) at -20 ° C using the corresponding compound instead of the compound prepared in Reference Example 4. Ethoxymethyl chloride is used instead of methyl chloride.) → 2 (S) -2 obtained by the same procedure as shown in Example 43 (using allyl bromide instead of benzyl bromide). -Propenyl-4 (S) -ethoxymethoxymethyl-4- (N- (4-phenoxyphenylcarbonyl) aminobutanoic acid methyl ester (1.06
g) in tetrahydrofuran (4 ml) was added dropwise.
The mixture was stirred at −15 ° C. for 30 minutes. A saturated ammonium chloride solution and water were added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by silica gel chromatography (toluene: ethyl acetate = 87: 13). Purified compound (200m
Using g), a similar operation to the method described in Example 2 was carried out to give the title compound (193 mg) having the following physical data.
I got TLC: Rf 0.19 (chloroform: methanol = 9:
1).

Example 58 N-Hydroxy-2 (R) -allyl-5-ethoxymethoxy-4 (S)-[N- (4-phenoxyphenylcarbonyl) amino] pentanamide

Embedded image Using the compound prepared in Example 57, the title compound having the following physical data was obtained in the same manner as in the method shown in Example 3 → Example 4. TLC: Rf 0.23 (chloroform: methanol = 1
0: 1); NMR (d ₆ -DMSO): δ 10.37 (s, 1H), 8.74 (brs, 1
H), 8.13 (d, J = 8.1Hz, 1H), 7.90-7.85 (m, 2H), 7.45-
7.39 (m, 2H), 7.19 (t, J = 7.2Hz, 1H), 7.07-6.99 (m,
4H), 5.69-5.60 (m, 1H), 5.02-4.93 (m, 2H), 4.56
(s, 2H), 3.99-3.89 (m, 1H), 3.80-3.39 (m, 4H), 2.2
6-2.01 (m, 3H), 1.85-1.79 (m, 1H), 1.61-1.54 (m, 1
H), 1.07 (t, J = 7.2Hz, 3H).

Using the compounds corresponding to Examples 58 (1) to 58 (3) , the same procedures as in Example 57 → Example 58 were carried out to obtain the following compounds.

Example 58 (1) N-hydroxy-2 (R) -benzyl-5-methoxymethoxy-4 (S)-[N- [4- (benzofuran-2-
Yl) phenylcarbonyl] amino] pentanamide

Embedded image TLC: Rf 0.35 (chloroform: methanol = 1
9: 1); NMR (d ₆ -DMSO): δ 10.37 (1H, s), 8.72 (1H, s),
8.28 (1H, d, J = 7.2Hz), 8.02 (2H, d, J = 8.8Hz), 7.9
7 (2H, d, J = 8.8Hz), 7.74- 7.62 (2H, m), 7.57 (1H,
d, J = 0.6Hz), 7.41-7.10 (7H, m), 4.56 (2H, s), 4.18
-3.98 (1H, m), 3.57-3.39 (2H, m), 3.23 (3H, s), 2.8
5 (1H, dd, J = 13.6, 8.4Hz), 2.64 (1H, dd, J = 13.6,
6.0Hz), 2.54-2.40 (1H, m), 2.03-1.80 (1H, m), 1.72
-1.52 (1H, m).

Example 58 (2) N-hydroxy-2 (R) -methyl-5-ethoxymethoxy-4 (S)-[N- (4-phenoxyphenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.29 (chloroform: methanol: acetic acid = 100: 10: 1); NMR (d ₆ -DMSO): δ 10.35 (s, 1H), 8.70 (s, 1H),
8.13 (d, J = 8.1Hz, 1H), 7.88 (d, J = 8.4Hz, 2H), 7.4
5-7.39 (m, 2H), 7.19 (t, J = 7.2Hz, 1H), 7.07-7.01
(m, 4H), 4.57 (s, 2H), 4.01-3.88 (m, 1H), 3.47 (q,
J = 7.2Hz, 2H), 3.44-3.38 (m, 2H), 2.30-2.18 (m, 1
H), 1.91-1.82 (m, 1H), 1.55-1.46 (m, 1H), 1.07 (t,
J = 7.2Hz, 3H), 0.99 (d, J = 6.9Hz, 3H).

Example 58 (3) N-hydroxy-2 (R) -methyl-5-ethoxymethoxy-4 (S)-[N- [4- (4-cyanophenyl)
Phenylcarbonyl] amino] pentanamide

Embedded image TLC: Rf 0.49 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.36 (s, 1H), 8.69 (s, 1H),
8.28 (d, J = 8.2Hz, 1H), 8.00-7.94 (m, 6H), 7.84
(d, J = 8.4Hz, 2H), 4.57 (s, 2H), 4.06-3.88 (m, 1H),
3.52-3.42 (m, 4H), 2.34-2.18 (m, 1H), 1.95-1.81
(m, 1H), 1.60-1.45 (m, 1H), 1.07 (t, J = 7.2Hz, 3H),
1.00 (d, J = 6.6Hz).

Examples 59 (1) -59 (2) 4 (R) -carboxy-4-aminobutanoic acid methyl ester instead of 4 (S) -carboxy-4-aminobutanoic acid methyl ester, and prepared in Reference Example 4 Example 37 → Example 39 → Example 41 (In some cases, a corresponding compound may be used in place of methoxymethyl chloride) → Example 43 using a corresponding compound instead of the obtained compound.
(Use the corresponding compound in place of benzyl bromide.)
Using a compound obtained in the same manner as in the method shown in
By operating in the same manner as in Example 57 → Example 2 → Example 3 → Example 4, the following compounds were obtained.

Example 59 (1) N-hydroxy-2 (S) -benzyl-5-methoxymethoxy-4 (R)-[N- (4-phenoxyphenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.41 (chloroform: methanol: acetic acid: water = 100: 10: 1: 1); NMR (d ₆ -DMSO): δ 10.33 (1H, s), 8.69 (1H, s),
8.12 (1H, d, J = 8.0Hz), 7.85 (2H, d, J = 8.8Hz), 7.37-7.
46 (2H, m), 6.99-7.27 (10H, m), 4.52 (2H, s), 3.90-4.1
3 (1H, m), 3.38-3.44 (2H, m), 3.20 (3H, s), 2.81 (1H,
dd, J = 13.2Hz, 6.2Hz), 2.59 (1H, dd, J = 13.2Hz, 6.2H
z), 2.38-2.52 (1H, m), 1.79-1.93 (1H, m), 1.50-1.63 (1
H, m).

Example 59 (2) N-hydroxy-2 (S) -benzyl-5-methoxymethoxy-4 (R)-[N- [4- (3-phenoxy-1)
-Propynyl) phenylcarbonyl] amino] pentanamide

Embedded image TLC: Rf 0.41 (chloroform: methanol: acetic acid: water = 100: 10: 1: 1); NMR (d ₆ -DMSO): δ 10.31 (1H, s), 8.68 (1H, s),
8.24 (1H, d, J = 8.1Hz), 7.81 (2H, d, J = 7.8Hz), 7.51 (2
H, d, J = 7.8Hz), 7.32 (2H, t, J = 7.8Hz), 6.95-7.24 (8
H, m), 5.05 (2H, s), 4.50 (2H, s), 3.90-4.07 (1H, m),
3.37-3.42 (2H, m), 3.18 (3H, s), 2.79 (1H, dd, J = 13.
5Hz, 6.2Hz), 2.58 (1H, dd, J = 13.5Hz, 6.2Hz), 2.43-
2.52 (1H, m), 1.82-1.89 (1H, m), 1.54-1.62 (1H, m).

Examples 60 (1) to 60 (5) Example 37 → Example 39 → Example 41 (corresponding to methoxymethyl chloride) using the compound corresponding to the compound produced in Reference Example 4 Compound is used.) → Example 43 (using a corresponding compound instead of benzyl bromide) → Example 2 → Example 3 → Example 4 →
By operating in the same manner as in the method described in Example 27, the title compound having the following physical data was obtained.

Example 60 (1) N-hydroxy-2 (S)-(3-aminobenzyl)-
5-ethoxymethoxy-4 (S)-[N- (trans-
4-methylcyclohexylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.27 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.45-10.10 (brs, 1H), 8.80-
8.45 (brs, 1H), 7.40 (d, J = 8.1Hz, 1H), 6.86 (t, J =
7.7Hz, 1H), 6.35 (d, J = 7.7Hz, 1H), 6.32 (s, 1H),
6.28 (d, J = 7.7Hz, 1H), 4.85 (s, 2H), 4.54 (s, 2H),
3.95-3.80 (m, 1H), 3.55-3.20 (m, 4H, overlap with
H2O in DMSO), 2.59 (dd, J = 13.2, 8.4Hz, 1H), 2.45
(dd, J = 13.2, 5.7Hz, 1H), 2.32-2.20 (m, 1H), 2.08-
1.92 (m, 1H), 1.80-1.57 (m, 5H), 1.57-1.44 (m, 1
H), 1.44-1.20 (m, 3H), 1.11 (t, J = 7.1Hz, 3H), 0.96
-0.76 (m, 5H).

Example 60 (2) N-hydroxy-2 (S) -benzyl-5-ethoxymethoxy-4 (S)-[N- (4-carboxyphenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.22 (chloroform: methanol: acetic acid = 90: 10: 1); NMR (d ₆ -DMSO): δ 13.50-12.70 (br, 1H), 10.37
(s, 1H), 8.82-8.58 (br, 1H), 8.31 (d, J = 8.7Hz, 1
H), 8.01 (d, J = 8.7Hz, 2H), 7.95 (d, J = 8.7Hz, 2H),
7.27-7.08 (m, 5H), 4.58 (s, 2H), 4.34-4.19 (m, 1
H), 3.60-3.40 (m, 4H), 2.77 (d, J = 7.2, 2H), 2.42-2.
32 (m, 1H), 1.85-1.62 (m, 2H), 1.09 (t, J = 6.9Hz, 3
H).

Example 60 (3) N-hydroxy-2 (S) -benzyl-5-ethoxymethoxy-4 (S)-[N- (4-aminophenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.36 (methylene chloride: methanol = 1
9: 1); NMR (d ₆ -DMSO): δ 10.34 (brs, 1H), 8.65 (brs,
1H), 7.61 (brd, J = 9.0Hz, 1H), 7.58 (d, J = 8.4Hz, 2
H), 7.22-7.08 (m, 5H), 6.52 (d, J = 8.4Hz, 2H), 5.57
(brs, 2H), 4.55 (s, 2H), 4.20 (m, 1H), 3.50-3.40
(m, 4H), 2.74 (d, J = 7.2Hz, 2H), 2.35 (m, 1H), 1.80
-1.59 (m, 2H), 1.07 (t, J = 7.2Hz, 3H).

Example 60 (4) N-hydroxy-2 (S) -benzyl-5-ethoxymethoxy-4 (S)-[N- (4-piperidylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.50 (chloroform: methanol: acetic acid = 7: 2: 1); NMR (d ₆ -DMSO): δ 10.30 (brs, 1H), 7.47 (brd,
J = 9.0Hz, 1H), 7.25-7.08 (m, 5H), 4.53 (s, 2H), 3.9
3 (m, 1H), 3.43 (q, J = 6.9Hz, 2H), 3.35 (m, 2H), 2.9
4 (brd, J = 12.0Hz, 2H), 2.68 (m, 2H), 2.49 (m, 2H),
2.35-2.10 (m, 2H), 1.70-1.40 (m, 6H), 1.09 (t, J =
6.9Hz, 3H).

Example 60 (5) N-hydroxy-2 (S)-(3-hydroxybenzyl) -5-ethoxymethoxy-4 (S)-[N- (4-
Methylphenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.45 (methylene chloride: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.33 (s, 1H), 9.16 (s, 1H),
8.64 (s, 1H), 7.99 (brd, J = 8.4Hz, 1H), 7.75 (d, J =
8.4Hz, 2H), 7.23 (d, J = 8.4Hz, 2H), 6.97 (t, J = 7.2H
z, 1H), 6.51 (m, 3H), 4.55 (s, 2H), 4.17 (m, 1H),
3.50 (m, 2H), 3.44 (q, J = 7.2Hz, 2H), 2.62 (m, 2H),
2.33 (s, 3H), 2.33 (m, 1H), 1.80-1.60 (m, 2H), 1.0
6 (t, J = 7.2Hz, 3H).

Examples 61 (1) to 61 (13) The compound prepared in Example 1, or a compound obtained by operating the same method as in Example 1 using the corresponding compound, and benzyl bromide Alternatively, using the corresponding compound, the title compound having the following physical properties was obtained in the same manner as in the method shown in Example 43 → Example 2 → Example 3 → Example 4.

Example 61 (1) N-hydroxy-2-benzyl-4- [N- [4- (benzofuran-2-yl) phenylcarbonyl] amino]
Butyramide

Embedded image TLC: Rf 0.39 (chloroform: methanol = 1
0: 1); NMR (d ₆ -DMSO): δ 10.43 (1H, s), 8.52 (1H, t,
J = 5.6Hz), 8.00 (2H, d, J = 8.8Hz), 7.94 (2H, d, J = 8.8
Hz), 7.71-7.63 (2H, m), 7.57 (1H, s), 7.39-7.16 (7
H, m), 3.30-3.15 (2H, m), 2.83 (1H, dd, J = 8.6, 13.
6Hz), 2.66 (1H, dd, J = 6.2, 13.6Hz), 2.44-2.31 (1H,
m), 1.88-1.53 (2H, m).

Example 61 (2) N-hydroxy-2- (3-phenylpropyl) -4-
[N- [4- (benzofuran-2-yl) phenylcarbonyl] amino] butyramide

Embedded image TLC: Rf 0.41 (chloroform: methanol = 1
0: 1); NMR (d ₆ -DMSO): δ 10.48 (1H, s), 8.50 (1H, t,
J = 5.6Hz), 8.01 (2H, d, J = 8.8Hz), 7.95 (2H, d, J = 8.8
Hz), 7.71-7.63 (2H, m), 7.57 (1H, s), 7.39-7.11 (7
H, m), 3.25-3.15 (2H, m), 2.59-2.47 (2H, m), 2.18-
2.02 (1H, m), 1.82-1.36 (6H, m).

Example 61 (3) N-hydroxy-2- (2-phenylethyl) -4-
[N- [4- (benzofuran-2-yl) phenylcarbonyl] amino] butyramide

Embedded image TLC: Rf 0.47 (chloroform: methanol = 1
0: 1); NMR (CD ₃ OD): δ 7.98 (2H, d, J = 8.4 Hz), 7.89 (2
H, d, J = 8.4Hz), 7.64-7.60 (1H, m), 7.56-7.52 (1H,
m), 7.36-7.09 (7H, m), 7.32 (1H, brs), 3.51-3.24
(2H, m), 2.68-2.50 (2H, m), 2.28-2.14 (1H, m), 2.0
4-1.69 (4H, m).

Example 61 (4) N-hydroxy-2-benzyl-4- [N- [4- [2
E- (4-chlorophenyl) ethenyl] phenylcarbonyl] amino] butyramide

Embedded image TLC: Rf 0.46 (chloroform: methanol = 1
0: 1); NMR (d ₆ -DMSO): δ 10.41 (1H, brs), 8.76 (1H, b
rs), 8.41 (1H, t, J = 5.4Hz), 7.83 (2H, d, J = 8.4Hz),
7.66 (2H, d, J = 8.4Hz), 7.65 (2H, d, J = 8.8Hz), 7.4
4 (2H, d, J = 8.8Hz), 7.35-7.12 (7H, m), 3.28-3.15
(2H, m), 2.83 (1H, dd, J = 8.4, 13.2Hz), 2.65 (1H, d
d.J = 5.8, 13.2Hz), 2.46-2.30 (1H, m), 1.86-1.51 (2
H, m).

Example 61 (5) N-hydroxy-2-benzyl-4- [N- (4-phenoxyphenylcarbonyl) amino] butyramide

Embedded image TLC: Rf 0.45 (chloroform: methanol = 1
0: 1); NMR (d ₆ -DMSO): δ 10.40 (1H, s), 8.75 (1H, br)
s), 8.35 (1H, t, J = 5.6Hz), 7.84 (2H, d, J = 8.8Hz),
7.47-7.38 (2H, m), 7.30-6.99 (10H, m), 3.26-3.14
(2H, m), 2.82 (1H, dd, J = 8.4, 13.6Hz), 2.64 (1H, d
d, J = 6.2, 13.6Hz), 2.43-2.28 (1H, m), 1.84-1.49 (2
H, m).

Example 61 (6) N-hydroxy-2- (naphthalen-1-yl) methyl-4- [N- (4-phenoxyphenylcarbonyl) amino] butyramide

Embedded image TLC: Rf 0.45 (chloroform: methanol = 1
0: 1); NMR (d ₆ -DMSO): δ 10.39 (1H, brs), 8.74 (1H, b
rs), 8.33 (1H, t, J = 5.4Hz), 8.08-8.03 (1H, m), 7.9
2-7.75 (2H, m), 7.81 (2H, d, J = 8.8Hz), 7.54-7.40
(9H, m), 7.00 (2H, d, J = 8.8Hz), 3.33-3.07 (4H, m),
2.63-2.45 (1H, m), 1.96-1.56 (2H, m).

Example 61 (7) N-hydroxy-2-isopropyl-4- [N- (4-
Phenoxyphenylcarbonyl) amino] butyramide

Embedded image TLC: Rf 0.35 (chloroform: methanol = 1
0: 1); NMR (d ₆ -DMSO): δ 10.39 (1H, brs), 8.34 (1H,
t, J = 5.6Hz), 7.90 (2H, d, J = 8.8Hz), 7.43 (2H, t, J
= 7.4Hz), 7.19 (1H, t, J = 7.4Hz), 7.09-7.04 (2H, m),
7.01 (2H, d, J = 8.8Hz), 3.22-3.06 (2H, m), 1.78-1.
61 (4H, m), 0.87 (3H, d, J = 6.8Hz), 0.83 (3H, d, J =
6.0Hz).

Example 61 (8) N-hydroxy-2- (quinolin-4-yl) methyl-
4- [N- (4-phenoxyphenylcarbonyl) amino] butyramide

Embedded image TLC: Rf 0.38 (chloroform: methanol = 1
0: 1); NMR (d ₆ -DMSO): δ 10.41 (1H, brs), 8.76 (1H, b
rs), 8.76 (1H, d, J = 4.4Hz), 8.37 (1H, t, J = 5.6Hz),
8.15 (1H, br.d, 7.6Hz), 8.00 (1H, d, J = 7.4Hz), 7.
83 (2H, d, J = 8.8Hz), 7.77-7.69 (1H, m), 7.62-7.54
(1H, m), 7.47-7.38 (2H, m), 7.30 (1H, d, J = 4.4Hz),
7.23-7.16 (1H, m), 7.08-7.05 (2H, m), 7.01 (2H,
d, J = 8.8Hz), 3.33-3.14 (4H, m), 2.64-2.50 (1H, m),
1.98-1.58 (2H, m).

Example 61 (9) N-hydroxy-2- (2-pyridyl) methyl-4-
[N- (4-phenoxyphenylcarbonyl) amino]
Butyramide

Embedded image TLC: Rf 0.34 (chloroform: methanol = 1
0: 1); NMR (d ₆ -DMSO): δ 10.47 (1H, brs), 8.76 (1H,
s), 8.47-8.43 (1H, m), 8.34 (1H, t, J = 5.6Hz), 7.83
(2H, d, J = 8.8Hz), 7.66 (1H, dt, J = 1.8, 7.6Hz), 7.
46-7.39 (2H, m), 7.23-7.15 (3H, m), 7.09-7.03 (2H, m
m), 7.01 (2H, d, J = 8.8Hz), 3.25-3.12 (2H, m), 2.97
(1H, dd, J = 7.6, 13.6Hz), 2.78 (1H, dd, J = 6.6, 13.6
Hz), 2.76-2.56 (1H, m), 1.85-1.46 (2H, m).

Example 61 (10) N-hydroxy-2- (3-pyridyl) methyl-4-
[N- (4-phenoxyphenylcarbonyl) amino]
Butyramide

Embedded image TLC: Rf 0.20 (chloroform: methanol = 1
0: 1); NMR (d ₆ -DMSO): δ 10.41 (1H, brs), 8.76 (1H,
s), 8.40-8.37 (3H, m), 7.85 (2H, d, J = 8.8Hz), 7.56
(1H, dt, J = 7.6, 2.2Hz), 7.47-7.38 (2H, m), 7.30-7.
16 (2H, m), 7.10-7.04 (2H, m), 7.02 (2H, d, J = 8.8H
z), 3.30-3.13 (2H, m), 2.87-2.66 (2H, m), 2.44-2.30
(1H, m), 1.86-1.52 (2H, m).

Example 61 (11) N-hydroxy-2- (naphthalen-2-yl) methyl-4- [N- (4-phenoxyphenylcarbonyl) amino] butyramide

Embedded image TLC: Rf 0.45 (chloroform: methanol = 1
0: 1); NMR (d ₆ -DMSO): δ 10.40 (1H, d, J = 1.4 Hz), 8.74
(1H, d, J = 1.4Hz), 8.36 (1H, t, J = 5.6Hz), 7.84 (2
H, d, J = 8.8Hz), 7.83-7.79 (3H, m), 7.65 (1H, brs),
7.50-7.33 (5H, m), 7.19 (1H, tt, J = 1.8, 7.4Hz),
7.09-7.04 (2H, m), 7.01 (2H, d, J = 8.8Hz), 3.30-3.1
2 (2H, m), 2.98 (1H, dd, J = 8.8, 13.6Hz), 2.83 (1H,
(dd, J = 6.0, 13.6Hz), 2.50-2.40 (1H, m), 1.90-1.54
(2H, m).

Example 61 (12) N-hydroxy-2- (4-pyridyl) methyl-4-
[N- (4-phenoxyphenylcarbonyl) amino]
Butyramide

Embedded image TLC: Rf 0.17 (chloroform: methanol = 1
0: 1); NMR (d ₆ -DMSO): δ 10.44 (1H, brs), 8.78 (1H, b
rs), 8.42 (2H, d, J = 5.8Hz), 8.38 (1H, t, J = 5.6Hz),
7.85 (2H, d, J = 8.8Hz), 7.47-7.38 (2H, m), 7.23-7.1
5 (3H, m), 7.10-7.05 (2H, m), 7.02 (2H, d, J = 8.8H
z), 3.30-3.13 (2H, m), 2.87-2.66 (2H, m), 2.48-2.33
(1H, m), 1.85-1.52 (2H, m).

Example 61 (13) N-hydroxy-2- (3-methoxybenzyl) -4-
[N- (4-phenoxyphenylcarbonyl) amino]
Butyramide

Embedded image TLC: Rf 0.41 (chloroform: methanol = 1
0: 1); NMR (d ₆ -DMSO): δ 10.40 (1H, s), 8.76 (1H, br)
s), 8.35 (1H, t, J = 5.6Hz), 7.84 (2H, d, J = 8.8Hz),
7.47-7.39 (2H, m), 7.24-7.04 (4H, m), 7.01 (2H, d,
J = 8.8Hz), 6.75-6.70 (3H, m), 3.70 (3H, s), 3.30-3.
10 (2H, m), 2.79 (1H, dd, J = 8.8, 13.4Hz), 2.61 (1
(H, dd, J = 6.2, 13.4Hz), 2.43-2.29 (1H, m), 1.83-1.48
(2H, m).

Example 62 N-Hydroxy-2-isobutyl-4- [N- (4-phenoxyphenylcarbonyl) amino] butyramide

Embedded image Example 43 → Example 27 → Example 2 → Using a compound obtained by the same procedure as described in Example 1 using the corresponding compound and 3-bromo-2-methylpropene,
By operating in the same manner as in Example 3 → Example 4, the title compound having the following physical data was obtained. TLC: Rf 0.33 (chloroform: methanol = 1
0: 1); NMR (d ₆ -DMSO): δ 10.47 (1H, s), 9.10-8.41 (1
H, brs), 8.33 (1H, t, J = 5.2Hz), 7.85 (2H, d, J = 8.8H
z), 7.23 (2H, t, J = 7.4Hz), 7.19 (1H, t, J = 7.4Hz),
7.09-7.04 (2H, m), 7.01 (2H, d, J = 8.8Hz), 3.21-3.1
1 (2H, m), 2.22-2.04 (1H, m), 1.76-1.34 (4H, m),
1.16-1.02 (1H, m), 0.84 (3H, d, J = 5.4Hz), 0.81 (3
H, d, J = 5.8Hz).

Example 63 5-methoxy-4 (S)-[N- [4- (4-chlorophenyl) phenylcarbonyl] amino] pentanoic acid

Embedded image 5-Hydroxy-4 obtained by the same procedure as in Example 37 → Example 38 using the corresponding compound.
(S)-[N- (4'-chlorobiphenyl-4-yl)
Carbonyl] aminopentanoic acid methyl ester (1.7
g) in tetrahydrofuran (5 ml), silica gel (500 mg) and diazomethane ether (4 m
l) The solution was added. The mixture was stirred at room temperature for 10 minutes.
The reaction solution was concentrated. Residual tetrahydrofuran (5m
l) To the solution was added a solution of diazomethane in ether (4 ml), and the mixture was stirred for 10 minutes. This operation was repeated 10 times. The residue was purified by silica gel column chromatography (hexane: ethyl acetate = 9: 1 → 3: 1) to give the methyl ester of the title compound (1.42 g). The title compound (1.2 g) having the following physical data was obtained in the same manner as in Example 2, using the methyl ester (1.4 g). TLC: Rf 0.50 (methylene chloride: methanol = 9:
1).

Example 64 N-Hydroxy-5-methoxy-4 (S)-[N- [4
-(4-chlorophenyl) phenylcarbonyl] amino] pentanamide

Embedded image Using the compound prepared in Example 63, the same procedure as in Example 3 → Example 4 was carried out to give the title compound having the following physical data. TLC: Rf 0.38 (chloroform: methanol = 1
0: 1); NMR (d ₆ -DMSO): δ 10.35 (1H, brs), 8.27 (1H,
d, J = 8.4Hz), 7.95 (2H, d, J = 8.4Hz), 7.77 (2H, d, J
= 8.4Hz), 7.76 (2H, d, J = 8.8Hz), 7.54 (2H, d, J = 8.8
Hz), 4.20-4.03 (1H, m), 3.42 (1H, dd, J = 6.2, 9.6H
z), 3.33 (1H, dd, J = 6.2, 9.6Hz), 3.26 (3H, s), 2.0
8-1.95 (2H, m), 1.94-1.58 (2H, m).

Reference Example 7 2 (S) -methyl-5-hydroxy-4 (S)-(N-
Benzyloxycarbonyl) aminopentanoic acid t-butyl ester

Embedded image Example 39 → Example 45 → Example 46 using 4 (S) -carboxy-4- (N-benzyloxycarbonylamino) butanoic acid t-butyl ester (using methyl iodide instead of benzyl bromide) ) → The title compound having the following physical data was obtained in the same manner as in Example 48. TLC: Rf 0.36 (hexane: ethyl acetate = 3:
1).

Example 65 2 (S) -Methyl-5-succinimide-4 (S)-
[N- (4-chlorophenylcarbonyl) amino] pentanoic acid

Embedded image The compound produced in Reference Example 7 (1.42 g), succinimide (521 mg) and triphenylphosphine (1.38 g)
g) in anhydrous tetrahydrofuran (20 ml),
Cooled to 0 ° C. To the mixture was added dropwise diethyl azodicarboxylate (2.3 ml; 40% toluene solution),
Stirred for hours. The reaction mixture was concentrated. The residue is purified by silica gel or ram chromatography (hexane: acetone =
9: 1, hexane: ethyl acetate = 3: 1 → 2: 1)
The product was purified twice to obtain a mixture (2.09 g) of the target substance and triphenylphosphine oxide. This mixture of methanol (2
0%) solution, 10% palladium on carbon (400mg)
Was added and stirred at room temperature for 1 hour under a hydrogen atmosphere. The reaction mixture was filtered through Celite (trade name), and the filtrate was concentrated. The residue was dissolved in dichloromethane (20 ml),
And cooled. To this solution was added triethylamine (2 ml) and p-chlorobenzoyl chloride (1.10 g),
Stirred at 0 ° C. for 2 hours. The reaction mixture was diluted with ethyl acetate, washed successively with 1N hydrochloric acid, water, a saturated aqueous solution of sodium carbonate, water and saturated saline, dried over anhydrous sodium sulfate and concentrated. The residue was purified by silica gel or column chromatography (hexane: ethyl acetate = 3: 1 → 2: 1 → 3:
Purification in 2) gave the t-butyl ester of the title compound (1.29 g). The same operation as in Example 29 was performed using the t-butyl ester (1.07 g) to give the title compound (845 mg) having the following physical data.
I got TLC: Rf 0.40 (methylene chloride: methanol = 9:
1); NMR (CDCl ₃ ): δ 7.64 (d, J = 9.0 Hz, 2H), 7.35
(d, J = 9.0Hz, 2H), 6.55 (d, J = 8.7Hz, 1H), 4.51
(m, 1H), 3.69 (dd, J = 13.8, 9.3Hz, 1H), 3.62 (dd,
J = 13.8, 4.2Hz, 1H), 2.75-2.51 (m, 5H), 1.97 (dd
d, J = 14.4, 10.8, 7.2Hz, 1H), 1.65 (ddd, J = 14.
4, 6.3, 4.2Hz, 1H), 1.26 (d, J = 7.2Hz, 3H).

Example 66 N-hydroxy-2 (S) -methyl-5-succinimide-4 (S)-[N- (4-chlorophenylcarbonyl) amino] pentanamide

Embedded image Using the compound prepared in Example 65, the title compound having the following physical data was obtained in the same manner as in the method shown in Example 3 → Example 4. TLC: Rf 0.42 (methylene chloride: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.35 (d, J = 1.5 Hz, 1H), 8.65
(d, J = 1.5Hz, 1H), 8.12 (d, J = 9.0Hz, 1H), 7.75 (d,
J = 8.4Hz, 2H), 7.51 (d, J = 8.4Hz, 2H), 4.22 (m, 1H),
3.49 (m, 2H), 2.53 (m, 4H), 2.17 (m, 1H), 1.70 (d
dd, J = 13.8, 10.5, 5.4Hz, 1H), 1.50 (ddd, J = 13.8,
9.0, 4.5Hz, 1H), 0.96 (d, J = 6.9Hz, 3H).

Example 66 (1) N-hydroxy-2 (S) -methyl-5-succinimidooxy-4 (S)-[N-methyl-N- (4-nitrophenylcarbonyl) amino] pentanamide

Embedded image Example 65 (Using N-hydroxysuccinimide instead of succinimide and p-chlorobenzoyl chloride instead of p-chlorobenzoyl chloride)
-Nitrobenzoyl chloride, and the t-butyl ester is used in the next reaction. ) → Example 5 → Example 29 → The same procedure as in Example 66 was carried out to obtain the title compound having the following physical data. TLC: Rf 0.45 (methylene chloride: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.50 (s, 0.7H), 10.45 (s,
0.3H), 8.28 (d, J = 9.0Hz, 1.4H), 8.24 (d, J = 9.0Hz,
0.6H), 7.69 (d, J = 9.0Hz, 1.4H), 7.61 (d, J = 9.0Hz,
0.6H), 4.86 (m, 0.7H), 4.20-4.00 (m, 2H), 3.72 (m,
0.3H), 2.89 (s, 0.9H), 2.71 (s, 2.1H), 2.60 (m, 4
H), 2.20-1.70 (m, 2H), 1.60-1.30 (m, 1H), 1.05 (d,
J = 6.9Hz, 2.1H), 0.74 (d, J = 6.9Hz, 0.9H).

Reference Example 8 5-ethoxymethoxy-4 (S)-[N- (4-phenoxyphenylcarbonyl) amino] pentanol

Embedded image Example 37 was repeated using the corresponding compound instead of Reference Example 4.
→ Example 39 → Example 41 → 5-ethoxymethoxy-4 obtained in the same manner as described in Example 42.
(S)-(N- (4-phenoxyphenylcarbonyl)
Aminopentanoic acid (3.62 g) in tetrahydrofuran (1
After cooling the solution to 0 ° C, triethylamine (1.
69 ml) and ethyl chloroformate (1.2 ml) were added dropwise. The mixture was stirred at 0 ° C. for 1.5 hours. To the reaction mixture was added sodium borohydride (0.5 equivalent),
After stirring for 0 minutes, acetic acid (5 ml) was added dropwise and stirred for 30 minutes. The reaction solution was concentrated. Ethyl acetate and water were added to the residue, and the organic layer was separated. The organic layer was washed with water and a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by silica gel column chromatography (ethyl acetate: hexane = 2: 1 (containing 1% triethylamine) → 4: 1) to give the title compound (1.84 g) having the following physical data. TLC: Rf 0.52 (ethyl acetate: hexane = 4:
1).

Reference Example 9 1-bromo-5-ethoxymethoxy-4 (S)-[N-
(4-phenoxyphenylcarbonyl) amino] pentane

Embedded image To a solution of the compound (490 mg) produced in Reference Example 8 in methylene chloride (10 ml) was added triphenylphosphine (40 ml).
9 mg) and sodium hydrogen carbonate (328 mg) were added, and the mixture was cooled to 0 ° C. Add carbon tetrabromide (647 m
g) in methylene chloride (5 ml) was added dropwise at 0 ° C.
Stir for 5 minutes. The reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with water and saturated sodium chloride, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by silica gel column chromatography (hexane: ethyl acetate = 3: 1) to give the title compound (293 g) having the following physical data. TLC: Rf 0.41 (hexane: ethyl acetate = 2:
1).

Example 67 1-acetylthio-5-ethoxymethoxy-4 (S)-
[N- (4-phenoxyphenylcarbonyl) amino]
Pentane

Embedded image To a solution of the compound (290 mg) produced in Reference Example 9 in acetone (8 ml) was added potassium thioacetate (113 mg), and the mixture was refluxed for 2 hours. After cooling, pour the reaction solution into water,
Extracted with ethyl acetate. The extract was washed with water and a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate,
Concentrated. The residue was purified by silica gel or ram chromatography (hexane: ethyl acetate = 3: 1) to give the title compound (268 mg) having the following physical data. TLC: Rf 0.28 (hexane: ethyl acetate = 2:
1). NMR (CDCl ₃ ): δ 7.77 (d, J = 8.7 Hz, 2H), 7.38
(t, J = 7.5Hz, 2H), 7.17 (t, J = 7.5Hz, 1H), 7.05 (d, J
= 7.5Hz) and 7.01 (d, J = 8.7Hz) total 4H, 6.54 (d, J
= 8.7Hz, 1H), 4.72 (d, J = 6.9Hz, 1H), 4.68 (d, J = 6.9
Hz, 1H), 4.35-4.25 (m, 1H), 3.74 (dd, J = 10, 3Hz, 1
H), 3.63-3.58 (m, 3H), 2.92 (t, J = 6.9Hz, 2H), 2.32
(s, 3H), 1.80-1.65 (m, 4H), 1.21 (t, J = 7.2Hz, 3
H).

Example 68 5-ethoxymethoxy-4 (S)-[N- (4-phenoxyphenylcarbonyl) amino] pentanethiol

Embedded image To a solution of the compound (230 mg) prepared in Example 67 in methanol (5 ml) was added potassium carbonate (146 m 2) at room temperature.
g) was added and stirred for 2 hours. The reaction solution was poured into ice / 1N hydrochloric acid and extracted with ethyl acetate. The extract was washed with water and a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by silica gel column chromatography (hexane: ethyl acetate = 3: 1),
The title compound (170 mg) having the following physical data was obtained. TLC: Rf 0.27 (hexane: ethyl acetate = 2:
1), NMR (CDCl ₃ ): δ 7.77 (d, J = 9 Hz, 2H), 7.40-7.34
(m, 2H), 7.17 (t, J = 7.5Hz, 1H), 7.08-6.96 (m, 4
H), 6.54 (d, J = 9Hz, 1H), 4.73 (d, J = 6.9Hz, 1H), 4.
69 (d, J = 6.9Hz, 1H), 4.34-4.24 (m, 1H), 3.77 (dd,
J = 10.2, 3Hz, 1H), 3.66-3.56 (m, 3H), 2.63- 2.53
(m, 2H), 1.83-1.65 (m, 4H), 1.37 (t, J = 7.5Hz, 1H),
1.22 (t, J = 7.2Hz, 3H).

Example 69 Methyl 5-ethoxymethoxy-4 (S)-[N- (4-phenoxyphenylcarbonyl) amino] pentanoate

Embedded image Example 39 → Method 41 (Using ethoxymethyl chloride instead of methoxymethyl chloride) using methyl 4 (S) -carboxy-4- (N-benzyloxycarbonylamino) butanoate. Methanol (150 g) of 5 (S) -ethoxymethoxy-4 (S)-(benzyloxycarbonyl) aminopentanoic acid methyl ester (10 g) obtained by the same operation.
ml) solution, 10% palladium on carbon (1 g) was added,
The mixture was heated under reflux in a hydrogen atmosphere for 2 hours. The reaction mixture was cooled, insolubles were filtered through celite, and the filtrate was concentrated. To a solution of the residue in dimethylformamide (DMF) (150 ml) was added 1-hydroxybenzotriazole monohydrate (4.
8 g) and 4-phenoxybenzoic acid (6 g) were added,
The mixture was ice-cooled, 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride (6.5 g) was added, and then triethylamine (4.7 ml) was added dropwise, followed by stirring at room temperature overnight. Water was added to the reaction mixture, and extracted with ethyl acetate. The extract was washed with 1N hydrochloric acid, a saturated aqueous solution of sodium carbonate, and a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, and concentrated. The residue was washed with n-hexane to give the title compound (8.1 g) having the following physical data.
I got TLC: Rf 0.22 (n-hexane: ethyl acetate = 1:
1).

Example 70 2 (S) -Methyl-5-ethoxymethoxy-4 (S)-
[N- (4-phenoxyphenylcarbonyl) amino]
Pentanoic acid

Embedded image Example 43 (Using methyl iodide instead of benzyl bromide) using the compound prepared in Example 69 → The title compound having the following physical property values was operated in the same manner as in the method shown in Example 2. The compound was obtained. TLC: Rf 0.45 (chloroform: methanol: acetic acid: water = 100: 10: 1: 1), NMR (DMSO-d ₆ ): d 7.75 (2H, d, J = 8.8 Hz), 7.37 (2
H, m), 7.17 (1H, t, J = 7.4Hz), 7.03 (2H, m), 6.97 (2H,
d, J = 8.8Hz), 6.58 (1H, d, J = 9.1Hz), 4.71 (1H, d, J =
6.9Hz), 4.68 (1H, d, J = 6.9Hz), 4.43 (1H, m), 3.74 (1
H, dd, J = 3.0, 10.2Hz), 3.65-3.55 (3H, m), 2.56 (1H,
m), 2.16 (1H, m), 1.68 (1H, m), 1.27 (3H, d, J = 6.9Hz),
1.18 (3H, t, J = 7.1Hz).

Using the compounds corresponding to Examples 70 (1) and 70 (2) , the same procedures as in Example 69 → Example 70 were carried out to obtain the following compounds.

Example 70 (1) 2 (S) -Allyl-5-ethoxymethoxy-4 (S)-
[N- (4-phenoxyphenylcarbonyl) amino]
Pentanoic acid

Embedded image TLC: Rf 0.49 (chloroform: methanol: acetic acid = 100: 10: 1).

Example 70 (2) 2 (S) -Methyl-5-ethoxymethoxy-4 (S)-
[N- [4- (4-cyanophenyl) phenylcarbonyl] amino] pentanoic acid

Embedded image _{NMR (DMSO-d 6):} d 12.7 (1H, s), 8.29-8.25 (2H,
m), 7.97-7.92 (6H, m), 7.83 (2H, d, J = 8.4Hz), 4.59 (2H
H, s), 4.28-4.16 (1H, m), 3.53-3.42 (4H, m), 2.39-2.
30 (1H, m), 1.95-1.84 (1H, m), 1.64-1.54 (1H, m), 1.1
2-1.04 (6H, m).

Example 71 N-hydroxy-2 (S) -methyl-5-ethoxymethoxy-4 (S)-[N- (4-phenoxyphenylcarbonyl) amino] pentanamide

Embedded image Using the compound prepared in Example 70 and performing the same operations as in the method shown in Example 3 → Example 4, the title compound having the following physical data was obtained. TLC: Rf 0.40 (chloroform: methanol: acetic acid: water = 100: 10: 1: 1); NMR (DMSO-d ₆ ): d 10.37 (1H, brs), 8.66 (1H, br)
s), 8.03 (1H, d, J = 8.8Hz), 7.87 (2H, d, J = 8.8Hz), 7.
43 (2H, dd, J = 7.4, 8.5Hz), 7.20 (1H, t, J = 7.4Hz), 7.
06 (2H, d, J = 8.5Hz), 7.02 (2H, d, J = 8.8Hz), 4.59 (2H,
s), 4.14 (1H, m), 3.50-3.45 (4H, m), 2.17 (1H, m),
1.66 (2H, m), 1.09 (3H, t, J = 7.1Hz), 1.01 (3H, d, J =
6.9Hz).

Examples 71 (1) to 71 (2) Using the compound prepared in Example 70 (1) or 70 (2), the same procedures as in Example 71 were carried out, and
The following compounds were obtained.

Example 71 (1) N-hydroxy-2 (S) -allyl-5-ethoxymethoxy-4 (S)-[N- (4-phenoxyphenylcarbonyl) amino] pentanamide

Embedded image TLC: Rf 0.26 (chloroform: methanol: acetic acid = 100: 10: 1); NMR (d ₆ -DMSO): δ 10.42 (1H, s), 8.70 (1H, s),
8.03 (1H, d, J = 8.8Hz), 7.89-7.85 (2H, m), 7.47-7.37 (2
H, m), 7.23-7.15 (1H, m), 7.09-6.99 (4H, m), 5.77-5.5
5 (1H, m), 5.03-4.92 (2H, m), 4.58 (2H, s), 4.19-4.05
(1H, m), 3.53-3.42 (2H, m), 3.47 (2H, q, J = 7.0Hz),
2.19-2.17 (3H, m), 1.38-1.82 (2H, m), 1.08 (3H, t, J =
7.0Hz).

Example 71 (2) N-hydroxy-2 (S) -methyl-5-ethoxymethoxy-4 (S)-[N- [4- (4-cyanophenyl)
Phenylcarbonyl] amino] pentanamide

Embedded image TLC: Rf 0.48 (chloroform: methanol = 9:
1); NMR (d ₆ -DMSO): δ 10.37 (1H, s), 8.18 (1H, d,
J = 8.4Hz), 7.99-7.91 (6H, m), 7.83 (2H, d, J = 8.2H
z), 4.58 (2H, s), 4.24-4.07 (1H, m), 3.54-3.41 (4
H, m), 2.26-2.10 (1H, m), 1.74-1.62 (2H, m), 1.12-
0.97 (6H, m).

Formulation Example Formulation Example 1 The following ingredients were mixed in a conventional manner and tabletted to give 100 tablets each containing 50 mg of the active ingredient. -N-hydroxy-2 (S) -methyl-5-ethoxymethoxy-4 (S)-[N- (4-phenoxyphenylcarbonyl) amino] pentanamide ... 5.0 g-Calcium carboxymethylcellulose (disintegrant) ... 0.2g ・ Magnesium stearate (lubricant) 0.1g ・ Microcrystalline cellulose 4.7g

Formulation Example 2 After mixing the following components by a conventional method, the solution is sterilized by a conventional method, filled into ampoules in 5 ml portions, freeze-dried by a conventional method, and contains 20 mg of the active ingredient in one ampule. 100 ampoules were obtained. -N-hydroxy-2 (S) -methyl-5-ethoxymethoxy-4 (S)-[N- (4-phenoxyphenylcarbonyl) amino] pentanamide 2.0 g Mannitol 20 g Distilled water 500ml

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁷ Identification symbol FI theme coat ゛ (Reference) A61K 31/341 A61K 31/341 31/343 31/343 31/381 31/381 31/385 31/385 31 / 40 31/40 31/403 31/403 31/4035 31/4035 31/405 31/405 31/415 31/415 31/4164 31/4164 31/4166 31/4166 31/4178 31/4178 31/435 31/435 31/44 31/44 31/4406 31/4406 31/4409 31/4409 31/4418 31/4418 31/4439 31/4439 31/445 31/445 31/451 31/451 31/454 31 / 454 31/47 31/47 31/495 31/495 31/4965 31/4965 31/5375 31/5375 A61P 1/02 A61P 1/02 1/16 1/16 7/00 7/00 9/00 9 / 00 9/10 101 9/10 101 11/00 11/00 13/12 13/12 15/00 15/00 19/02 19/02 19/10 19/10 27/02 27/02 29/00 101 29 / 00 101 35/00 35/00 35/02 35/02 35/04 35/04 37/00 37/00 43/00 111 43/00 111 C07C 233/82 C07C 233/82 235/16 235/16 Z 235/52 235/52 23 7/06 237/06 237/20 237/20 259/06 259/06 271/22 271/22 311/21 311/21 323/42 323/42 323/59 323/59 323/60 323/60 327 / 30 327/30 C07D 209/18 C07D 209/18 209/24 209/24 209/32 209/32 209/48 211/14 211/14 211/46 211/46 211/62 211/62 211/70 211 / 70 213/56 213/56 213/61 213/61 213/68 213/68 213/79 213/79 213/80 213/80 215/14 215/14 231/12 C 231/12 233/64 106 233 / 64 106 233/72 233/72 295/10 A 295/10 295/12 Z 295/12 295/14 Z 295/14 295/16 Z 295/16 307/68 307/68 307/80 307/80 307 / 84 307/84 333/16 333/16 333/40 333/40 333/60 333/60 339/08 339/08 401/12 401/12 403/12 403/12 405/12 405/12 C07F 7/18 A // C07F 7/18 C07D 209/48 Z

Claims (16)

[Claims] 1. A compound of the general formula (I)[Wherein, R¹Is -COOR^Ten, -CONHOR^Ten, -C
ONNHHR^Ten,-(CH_Two)_nSR⁵⁰Or -Y-PO
(OR⁵¹)_TwoAnd R^TenIs (i) a hydrogen atom, (ii) C
1-8 alkyl group, (iii) phenyl group, (iv) phenyl
Or a C1-8 alkoxy substituted with a C1-8 alkoxy group.
Alkyl group, or (v) phenyl group, benzyl group or
Table 1 shows oxycarbonyl groups substituted by C1-8 alkyl groups.
N represents an integer of 0 to 3;⁵⁰Is (i) hydrogen source
(Ii) C1-8 alkyl group, (iii) -COR
⁵²(In the group, R⁵²Is a C1-8 alkyl group or a phenyl group
Represents ), (Iv) -SR⁵³(In the group, R⁵³Is hydrogen field
, A C1-8 alkyl group or a phenyl group. )
And R⁵¹Is a hydrogen atom, a C1-8 alkyl group or
Represents a phenyl group, Y is a single bond, -CH_Two-Or-
O-^Two, R^Three, R^Four, R^Five, R⁶, R⁷Each
1) hydrogen atom, 2) C1-8 alkyl group, 3) C2-8 alkenyl group, 4) -OR¹¹, 5) -SR¹¹, 6) -NR¹²R¹³, 7) -COR¹⁴, 8) Cyc1, 9) -OR¹¹, -SR¹¹, -NR¹²R¹³, -COR¹⁴,
A guanidino group or a group selected from Cyc1 is substituted
C1-8 alkyl group, or 10) -OR¹¹, -SR¹¹, -NR¹²R¹³, -CO
R¹⁴A guanidino group or a group selected from Cyc1
Represents a substituted C2-8 alkenyl group, or^Three
Group and R^FourGroups together form a C1-8 alkylene group, R^FiveBase
And R⁶Groups together form a C1-8 alkylene group, R^ThreeGroup and
R⁶Groups together form a C1-8 alkylene group, R^TwoGroup and R
^ThreeGroups together form a C2-8 alkylene group, R^FourGroup and R^Five
Groups together form a C2-8 alkylene group, or R⁶Base
And R⁷The radicals together represent a C2-8 alkylene radical
Or R^TwoRepresents a 2-propynyl group;^Three,
R^Four, R^Five, R⁶, R⁷Each independently represents 1) a hydrogen atom, 2) a C1-8 alkyl group, 3) a C2-8 alkenyl group, 4) -OR¹¹, 5) -SR¹¹, 6) -NR¹²R¹³, 7) -COR¹⁴, 8) Cyc1, 9) -OR¹¹, -SR¹¹, -NR¹²R¹³, -COR¹⁴,
A guanidino group or a group selected from Cyc1 is substituted
C1-8 alkyl group, or 10) -OR¹¹, -SR¹¹, -NR¹²R¹³, -CO
R¹⁴A guanidino group or a group selected from Cyc1
Represents a substituted C2-8 alkenyl group, or^Three
Group and R^FourGroups together form a C1-8 alkylene group, R^FiveBase
And R⁶Groups together form a C1-8 alkylene group, R^ThreeGroup and
R⁶Groups together form a C1-8 alkylene group, R^FourGroup and R
^FiveGroups together form a C2-8 alkylene group, or R⁶Base
And R⁷The groups together represent a C2-8 alkylene group
Wherein Cyc1 represents a carbocyclic or heterocyclic ring
And one or more of these carbocycles or heterocycles
(I) C1-8 alkyl group, (ii) C1-8 alcohol
Xy group, (iii) nitro group, (iv) guanidino group, (v)
Amidino group, (vi) halogen atom, (vii) nitrile
Group, (viii) hydroxyl group, (ix) benzyloxy group, (x)
-NR¹⁰¹R¹⁰²(R¹⁰¹And R¹⁰²Are independent
Represents a hydrogen atom or a C1-8 alkyl group. ),
(Xi) -COOR¹⁰³(R¹⁰³Is a hydrogen atom or C1
Represents an 8 alkyl group. ), (Xii) trifluoromethyl
Group, (xiii) trifluoromethyloxy group, (xiv)
Phenyl group, (xv) C1-8 alkyl group or C1-8
A phenyl group substituted by an alkoxy group, (xv
i) phenyloxy group, (xvii) phenylsulfonyl group,
(Xviii) substituted by a phenyl group or a nitrile group
C1-8 alkyl group, (xix) heterocycle or (xx)
Keto group, (xxi) -CONR¹⁰⁴R¹⁰⁵Substituted with a group
1 to 8 alkoxy groups (in the group, R¹⁰⁴And R¹⁰⁵Is it
Each independently represents a hydrogen atom, a C1-8 alkyl group or
Represents a nyl group. ) May be substituted. R¹¹Is (i) a hydrogen atom, (ii) a C1-8 alkyl group, (iii) a Cyc1 group, (iv) -COR¹⁸Group, (v) -OR^Fifteen, -SR^Fifteen, -NR¹⁶R¹⁷, -CO
R¹⁸A guanidino group or a group selected from Cyc1
Represents a substituted C1-8 alkyl group,^FifteenIs a hydrogen atom, a C1-8 alkyl group, Cyc1,
Is C 1 substituted by Cyc1 or C1-8 alkoxy group
1 to 8 alkyl groups;¹⁶Represents a hydrogen atom or a C1-8 alkyl group;¹⁷Is a hydrogen atom, a C1-8 alkyl group or -COR¹⁹
(In the group, R¹⁹Is a C1-8 alkyl group, Cyc1 or C
yc1 represents a substituted C1-8 alkyl group. )
I, R¹⁸Is a hydroxyl group, a C1-8 alkyl group, a C1-8 alkoxy
Si group or -NR²⁰R ^{twenty one}(In the group, R²⁰And R^{twenty one}Is
Each independently a hydrogen atom, a C1-8 alkyl group, Cyc
Represents a C1-8 alkyl group substituted by 1 or Cyc1
You. ) And R¹²Is a hydrogen atom, C1-8 alkyl
Group, Cyc1 or C1-8 alkyl substituted with Cyc1
And represents R¹³Represents a hydrogen atom, a C1-8 alkyl group,
Cyc1, a C1-8 alkyl group substituted with Cyc1, or
Is -COR^{twenty two}(In the group, R^{twenty two}Is a C1-8 alkyl group, Cy
Table 1 represents a C1-8 alkyl group substituted by c1 or Cyc1.
I forgot. ) And R¹⁴Is a hydroxyl group, C1-8 alkyl
Group, C1-8 alkoxy group, Cyc1, Cyc1 substituted
C1-8 alkyl group or -NR^{twenty three}R^{twenty four}(In the group, R
^{twenty three}And R^{twenty four}Are each independently (i) a hydrogen atom, (i
i) a C1-8 alkyl group, (iii) Cyc1 or (iv)
Cyc1 or a C1-8 alkyl group substituted by a hydroxyl group
Express. ), And (1) R⁸Is 1) hydrogen atom, 2) C1-8 alkyl group, 3) C1-8 alkoxycarbonyl group, 4) —OR²⁶, -SR²⁶, -NR²⁷R²⁸Or -COR
²⁹A C1-8 alkyl group substituted by a group selected from:
Is 5) C1-8 alkoxycarbonyl substituted by Cyc2
When representing a group, R⁹IsAnd (2) R⁸IsWhen R represents⁹Is 1) C1-8 alkyl group, 2) C1-8 alkoxy group, 3) C1-8 alkoxy group substituted by Cyc2, 4) -OR²⁶, -SR²⁶, -NR²⁷R²⁸, -COR²⁹Ma
Or C1-8 alkyl substituted with a group selected from Cyc2
Or a groupWherein Cyc2 represents a carbocyclic or heterocyclic ring
Represents one or more of these carbocycles or heterocycles.
(I) a C1-8 alkyl group, (ii) a C1-8
Alkoxy, (iii) nitro, (iv) guanidino,
(V) amidino group, (vi) halogen atom, (vii) nitrile
A hydroxyl group, (ix) a benzyloxy group,
(X) -NR²⁰¹R²⁰²(R²⁰¹And R²⁰²Respectively
Independently represents a hydrogen atom or a C1-8 alkyl group
You. ), (Xi) -COOR²⁰³(R²⁰³Is a hydrogen atom or
Represents a C1-8 alkyl group. ), (Xii) trifle
Oromethyl group, (xiii) trifluoromethyloxy group,
(Xiv) a phenyl group, (xv) a C1-8 alkyl group or
Phenyl substituted by a C1-8 alkoxy group
Group, (xvi) phenyloxy group, (xvii) phenylsulfo
Nyl group, (xviii) phenyl group or nitrile group
A substituted C1-8 alkyl group, a (xix) heterocycle or
Is (xx) keto group, (xxi) -CONR²⁰⁴R²⁰⁵Substitute with group
C1-8 alkoxy group (in the group, R²⁰⁴And R²⁰⁵
Are each independently a hydrogen atom, a C1-8 alkyl group,
Or a phenyl group. ) May be substituted.
R²⁶Represents a hydrogen atom, a C1-8 alkyl group, Cyc2 or
Cyc2 represents a substituted C1-8 alkyl group;²⁷
Represents a hydrogen atom, a C1-8 alkyl group, Cyc2 or Cy
c2 represents a substituted C1-8 alkyl group;²⁸Is water
An element atom, a C1-8 alkyl group, Cyc2, Cyc2
Substituted C1-8 alkyl group or -COR³⁰(R³⁰Is C
1 to 8 alkyl groups, Cyc2 or Cyc2 substituted
Represents a C1-8 alkyl group. ) And R²⁹Is hydroxyl
Group, C1-8 alkyl group, Cyc2, Cyc2 is substituted
C1-8 alkyl group or -NR³¹R³²(R³¹and
R³²Are each independently a hydrogen atom, a C1-8 alkyl
Group, Cyc2 or C1-8 alkyl substituted with Cyc2
Represents a radical. ), AndRepresents a carbocyclic or heterocyclic ring;^{twenty five}Is -EG
And E is 1) a single bond, 2) -CONR³³-, 3) -NR³³CO-, 4) -CO-O-, 5) -O-CO-, 6) -NR³³-CO-NR³⁴-, 7) -CO-CH_Two-, 8) -CO-, 9) -O-CO-NR³³-, 10) -NR³³-CO-O-, 11) -O-CO-O-, 12) -CS-NR³³-, 13) -NR³³-CS-, 14) -CS-O-, 15) -O-CS-, 16) -NR³³-CS-R³⁴-, 17) -CS-CH_Two-, 18) -CS-, 19) -O-CS-NR³³-, 20) -NR³³-CS-O-, 21) -O-CS-O-, 22) -CH_Two-CH_Two-, 23) -HC = CH-, 24) -C≡C-, 25) -SO_Two-NR³³-, 26) -NR³³-SO_Two-, 27) -SO_Two-CH_Two-Or 28) -CH_Two-SO_Two-Represents a group represented by R³³And R³⁴Is independently a hydrogen atom, C
1-8 alkyl group, Cyc3 or Cyc3 substituted
Represents a C1-8 alkyl group, Cyc3 is a carbocyclic ring,
Represents a heterocycle, and these carbocycles or heterocycles are
One or more (i) C1-8 alkyl groups, (i
i) C1-8 alkoxy group, (iii) nitro group, (iv) group
Anidino group, (v) amidino group, (vi) halogen atom,
(Vii) nitrile group, (viii) hydroxyl group, (ix) benzyl
An oxy group, (x) -NR³⁰¹R³⁰²(R³⁰¹And R
³⁰²Is independently a hydrogen atom or C1-8
Represents a kill group. ), (Xi) -COOR³⁰³(R³⁰³Is
Represents a hydrogen atom or a C1-8 alkyl group. ), (Xi
i) trifluoromethyl group, (xiii) trifluoromethyl
Roxy group, (xiv) phenyl group, (xv) C1-8 al
Substituted by a kill group or a C1-8 alkoxy group
Phenyl group, (xvi) phenyloxy group, (xvii)
Phenylsulfonyl group, (xviii) phenyl group or nitro
A C1-8 alkyl group substituted by a ril group, (xix)
Heterocycle or (xx) keto group, (xxi) -CONR³⁰⁴R
³⁰⁵A C1-8 alkoxy group substituted with a group (in the group, R³⁰⁴
And R³⁰⁵Are each independently a hydrogen atom, C1-8
Represents an alkyl group or a phenyl group. ) Replaced by
May be. G is 1) hydrogen atom, 2) C1-8 alkyl group, 3) Cyc4, 4) -OR³⁵, 5) -SR³⁵6) halogen atom, 7) nitro group, 8) nitrile group, 9) -NR³⁶R³⁷, 10) -COR³⁸11) Cyc4, -OR³⁵, -SR³⁵, A halogen atom,
-NR³⁶R³⁷Or -COR³⁸A group selected from
Represents a C1-8 alkyl group, wherein Cyc4 is carbon
A heterocyclic ring or a heterocyclic ring.
The terrorist ring may have one or more (i) C1-8 alkyl
A group, (ii) a C1-8 alkoxy group, (iii) a nitro group,
(Iv) guanidino group, (v) amidino group, (vi) halogen
Atom, (vii) nitrile group, (viii) hydroxyl group, (ix)
Benzyloxy group, (x) -NR⁴⁰¹R⁴⁰²(R⁴⁰¹and
R⁴⁰²Are each independently a hydrogen atom or a C1-8
Represents an alkyl group. ), (Xi) -COOR⁴⁰³(R
⁴⁰³Represents a hydrogen atom or a C1-8 alkyl group
You. ), (Xii) trifluoromethyl group, (xiii) tri
Fluoromethyloxy group, (xiv) phenyl group, (xv)
A C1-8 alkyl group or a C1-8 alkoxy group
Substituted phenyl group, (xvi) phenyloxy
Group, (xvii) phenylsulfonyl group, (xviii) phenyl
C1-8 alkyl substituted by a group or a nitrile group
Group, (xix) heterocycle, (xx) keto group, or (xxi)-
CONR⁴⁰⁴R⁴⁰⁵C1-8 alkoxy group substituted with a group
(In the group, R⁴⁰⁴And R⁴⁰⁵Are independently hydrogen sources
, A C1-8 alkyl group or a phenyl group. )
May be substituted. R³⁵Is a hydrogen atom, C1-8
Alkyl group, C1-8 alkoxy group, Cyc4 or Cy
c4 represents a substituted C1-8 alkyl group;³⁶Is water
An element atom, a C1-8 alkyl group, Cyc4 or Cyc4
Represents a substituted C1-8 alkyl group;³⁷Is hydrogen field
C1-8 alkyl, Cyc4, Cyc4 are substituted
C1-8 alkyl group or -COR³⁹(R³⁹Is C1
8 alkyl groups, Cyc4 or C1 substituted with Cyc4
Represents a -8 alkyl group. ) And R³⁸Is a hydroxyl group,
C1-8 alkyl group, Cyc4, C substituted by Cyc4
1-8 alkyl group, -NR⁴⁰R⁴¹(R⁴⁰And R⁴¹Haso
Each independently a hydrogen atom, a C1-8 alkyl group, Cyc
Represents a C1-8 alkyl group substituted by 4 or Cyc4
You. ), Or together with -EG
P represents an integer of 1 to 5;
M represents a C1-8 alkylene group, and J represents a single bond
If an oxygen atom, a sulfur atom or -NR⁴²− (R⁴²Is hydrogen
Represents an atom or a C1-8 alkyl group. ), AndIs a single bond or R^Two, R^Three, R^Four, R^Five, R⁶, R⁷Out of
Two adjacent groups that are not bonded to the same carbon are hydrogen
In the case where R is removed, it represents a double bond (provided that R ^ThreeGroup and
R^FourGroups together form a C1-8 alkylene group, R^FiveGroup and R
⁶Groups together form a C1-8 alkylene group, R^ThreeGroup and R⁶
When the groups together represent a C1-8 alkylene group,
Does not represent a double bond. ). Where R¹Is -COOR
^TenOr -CONHOR^TenAnd R^TenIs a hydrogen source
Or a C1-8 alkyl group;^Four, R^FiveYou
And R⁸Each represents a hydrogen atom, and R^TwoAnd R
^ThreeOne of them represents a methyl group and the other one is hydrogen
Represents an atom and R⁶And R⁷Either one is et
Represents a xymethoxymethyl group, and the other one is a hydrogen atom
When expressing, R⁹Is(4-phenoxyphenyl group) is not represented. ]
Aminobutanoic acid derivatives, or non-toxic salts thereof. 2. R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ are each independently 1) a hydrogen atom, 2) a C1-8 alkyl group, 3) a C2-8 alkenyl group, 4) ^{-OR 11, 5) -SR 11,} 6) -NR 12 R 13, 7) -COR 14, 8) Cyc1, 9) -OR 11, -SR 11, -NR 12 R 13, -COR 14,
C1~8 alkyl group selected from guanidino group or Cyc1 is substituted or ^{10) -OR 11, -SR 11,} , -NR 12 R 13, -CO
R ¹⁴ represents a C2-8 alkenyl group substituted by a group selected from a guanidino group or Cyc1, or R ³
Group and R ⁴ group together, a C1-8 alkylene group, R ⁵ group and R ⁶ group together, a C1-8 alkylene group, R ³ and R ⁶ group together, a C1-8 alkylene group Group, R ² group and R
³ groups together C2~8 alkylene group, R ⁴ group and R ⁵
Groups together are C2~8 alkylene group or compound according to claim 1, wherein the R ⁶ groups and R ⁷ groups represents a C2~8 alkylene group together. Wherein represents R ² is 2-propynyl group, R ^{3,
R 4, R 5, R 6} , R 7 are each independently 1) hydrogen, 2) C1-8 alkyl group, 3) C2-8 alkenyl ^{group, 4) -OR 11, 5)} -SR 11, 6 ^{) -NR 12 R 13, 7)} -COR 14, 8) Cyc1, 9) -OR 11, -SR 11, -NR 12 R 13, -COR 14,
C1~8 alkyl group selected from guanidino group or Cyc1 is substituted or ^{10) -OR 11, -SR 11,} , -NR 12 R 13, -CO
R ¹⁴ represents a C2-8 alkenyl group substituted by a group selected from a guanidino group or Cyc1;
³ groups and R ⁴ group together form a C 1-8 alkylene group, R ⁵
Group and R ⁶ group together form a C1-8 alkylene group, R ³ group and R ⁶ group together form a C1-8 alkylene group, R ⁴ and R ⁵ group together form C2-8 alkylene Group, or R ⁶
The compound of claim 1, wherein the group the group R ⁷ represents since it C2~8 alkylene group together. 4. The compound according to claim 1, wherein R ¹ is a —COOR ¹⁰ group. 5. The compound according to claim ¹ , wherein R ¹ is a —CONHOR ¹⁰ group. 6. The compound according to claim ¹ , wherein R ¹ is a —CONNHHR ¹⁰ group. 7. The compound according to claim 1, wherein R ¹ is a — (CH ₂ ) _n SR ⁵⁰ group. 8. The compound according to claim 1, wherein R ¹ is —Y—PO (OR ⁵¹ ) ₂ . 9. The compound is (1) 4- (N- (4- (benzofuran-2-yl) phenylcarbonyl) amino)
Butanoic acid, (2) 4- (N- (4-methylphenylcarbonyl) amino) butanoic acid, (3) 4- (N- (4-butyloxyphenylcarbonyl) amino) butanoic acid,
(4) 4- (N- (3-butyloxyphenylcarbonyl) amino) butanoic acid, (5) 4- [N- [4- (2-
(4-methylphenyl) ethynyl) furan-2-ylcarbonyl] amino] butanoic acid, (6) 4- (N- (4-
(Pyrrole-1-yl) phenylcarbonyl) amino)
Butanoic acid, (7) 4- (N- (trans-4-methylcyclohexylcarbonyl) amino) butanoic acid, (8) 4
-(N- (4- (3-methoxy-1-propynyl) phenylcarbonyl) amino) butanoic acid, (9) 4- (N-
(4-butylphenylcarbonyl) amino) butanoic acid,
(10) 4- (N- (benzofuran-2-ylcarbonyl) amino) butanoic acid, (11) 4- [N- [4- (2-
(4-chlorophenyl) ethenyl) phenylcarbonyl] amino] butanoic acid, (12) 4- [N- [4- (2-
(4- (imidazol-1-yl) phenyl) ethynyl) phenylcarbonyl] amino] butanoic acid, (13) 4
-(N- (trans-4-propylcyclohexylcarbonyl) amino) butanoic acid, (14) 4- [N- [4-
(2- (4-methylphenyl) ethynyl) phenylcarbonyl] amino] butanoic acid, (15) 4- [N- [4-
((4-bromophenyl) aminosulfonyl) phenylcarbonyl] amino] butanoic acid, (16) 4- [N- (4
-Cyclohexylphenylcarbonyl) amino] butanoic acid, (17) 4- [N- [4- (4-propylphenyl)
Phenylcarbonyl] amino] butanoic acid, (18) 4-
[N- [4- (4-hydroxyphenyl) phenylcarbonyl] amino] butanoic acid, (19) 4- [N- [4-
(4-chlorophenyl) furan-2-ylcarbonyl]
Amino] butanoic acid, (20) 4- [N- [4- (4-heptylphenyl) phenylcarbonyl] amino] butanoic acid, (21) 4- [N- [4- (4-methoxyphenyl)
Phenylcarbonyl] amino] butanoic acid, (22) 4-
[N- [4- (4-chlorophenyl) phenylcarbonyl] amino] butanoic acid, (23) 4- [N- (5-benzyloxyindol-2-ylcarbonyl) amino] butanoic acid, (24) 4- [ N- [5- (2- (4-chlorophenyl) ethenyl) furan-2-ylcarbonyl] amino] butanoic acid, (25) 4- [N- (4-phenoxyphenylcarbonyl) amino] butanoic acid, (26) 4- (N-
Methyl-N- (4- (benzofuran-2-yl) phenylcarbonyl) amino) butanoic acid, (27) 4- (N-
(4- (benzofuran-2-yl) phenylcarbonyl) amino) -2 (S) -hydroxybutanoic acid, (28)
4- (N- (4- (benzofuran-2-yl) phenylcarbonyl) amino) -2 (R) -hydroxybutanoic acid, (29) 4- (N- (4- (benzofuran-2-yl) phenylcarbonyl ) Amino) -2 (S) -benzyloxymethoxybutanoic acid, (30) 4- (N- (4-
(Benzofuran-2-yl) phenylcarbonyl) amino) -2 (R) -benzyloxymethoxybutanoic acid, (3
1) 4- (N- (4- (2- (4-chlorophenyl) ethenyl) phenylcarbonyl) amino) -2 (S) -benzyloxymethoxybutanoic acid, (32) 4- (N- (4
-Chlorophenylcarbonyl) amino) -2-benzyloxymethoxybutanoic acid, (33) 4- (N- (4-chlorophenylcarbonyl) amino) -2-((N-benzyl-N-methylamino) carbonylmethoxy) butanoic acid , (34) 4- (N- (4-chlorophenylcarbonyl) amino) -2-((N-phenyl-N-methylamino) carbonylmethoxy) butanoic acid, (35) 4- (N-
(4-chlorophenylcarbonyl) amino) -2-
((N-phenylethyl-N-methylamino) carbonylmethoxy) butanoic acid, (36) 3 (S) -hydroxy-
4- (N- (4- (benzofuran-2-yl) phenylcarbonyl) amino) butanoic acid, (37) 3 (R) -hydroxy-4- (N- (4- (benzofuran-2-yl)
(Phenylcarbonyl) amino) butanoic acid, (38) 3
(S) -methoxymethyloxy-4- (N- (4- (benzofuran-2-yl) phenylcarbonyl) amino)
Butanoic acid, (39) 4- (N- (4- (benzofuran-2
-Yl) phenylcarbonyl) amino) -2-butenoic acid, (40) 3 (R) -methoxymethyloxy-4- (N
-(4- (benzofuran-2-yl) phenylcarbonyl) amino) butanoic acid, (41) 4- (N- (4- (benzofuran-2-yl) phenylcarbonyl) amino)-
3-butenoic acid, (42) 2-benzyloxymethyl-4-
(N- (4-methylphenylcarbonyl) amino) butanoic acid, (43) 4 (S) -methylaminocarbonyl-4-
(N- (4-methylphenylcarbonyl) amino) butanoic acid, (44) 4 (R) -methylaminocarbonyl-4-
(N- (4-methylphenylcarbonyl) amino) butanoic acid, (45) 4 (S) -benzylaminocarbonyl-4
-(N- (4-methylphenylcarbonyl) amino) butanoic acid, (46) 4 (S)-(4-hydroxybutyl) aminocarbonyl-4- (N- (4-methylphenylcarbonyl) amino) butanoic acid, (47) 4 (S) -methoxycarbonyl-4- [N- [4- (4-hydroxy-1-
Butynyl) phenylcarbonyl] amino] butanoic acid, (4
8) 4 (S) -t-butoxycarbonyl-4- (N-
(4-methylphenylcarbonyl) amino) butanoic acid,
(49) 4 (S)-(morpholin-1-yl) carbonyl-4- (N- (4- (benzofuran-2-yl) phenylcarbonyl) amino) butanoic acid, (50) 4 (S) -hydroxymethyl -4- (N- (4- (benzofuran-2
-Yl) phenylcarbonyl) amino) butanoic acid, (51)
4 (S) -methoxymethyloxymethyl-4- (N-
(4- (benzofuran-2-yl) phenylcarbonyl) amino) butanoic acid, (52) 2 (S) -benzyl-4
(S) -methoxymethyloxymethyl-4- (N- (4
-(Benzofuran-2-yl) phenylcarbonyl) amino) butanoic acid, (53) 2 (S) -methyl-4 (S)-
Methoxymethyloxymethyl-4- (N- (4- (benzofuran-2-yl) phenylcarbonyl) amino) butanoic acid, (54) 2 (S)-(3-phenyl-2-propenyl) -4 (S) -Methoxymethyloxymethyl-4-
(N- (4- (benzofuran-2-yl) phenylcarbonyl) amino) butanoic acid, (55) 2 (S)-(3-phenylpropyl) -4 (S) -methoxymethyloxymethyl-4- (N -(4- (benzofuran-2-yl) phenylcarbonyl) amino) butanoic acid, (56) 2 (S)
-Methyl-5-ethoxymethoxy-4 (S)-[N-
(4-Chlorophenylcarbonyl) amino] pentanoic acid, (57) 2 (S) -methyl-5-ethoxymethoxy-
4 (S)-[N- (4-nitrophenylcarbonyl) amino] pentanoic acid, (58) 2 (S) -methyl-5-ethoxymethoxy-4 (S)-[N- (4-bromophenylcarbonyl) Amino] pentanoic acid, (59) 2 (S) -allyl-5-ethoxymethoxy-4 (S)-[N- (4-
Nitrophenylcarbonyl) amino] pentanoic acid, (60)
2 (R) -methoxymethyl-5-ethoxymethoxy-
4 (S)-[N- (4-nitrophenylcarbonyl) amino] pentanoic acid, (61) 2 (R) -benzyloxymethyl-5-ethoxymethoxy-4 (S)-[N- (4-
Nitrophenylcarbonyl) amino] pentanoic acid, (62)
2 (S) -methyl-5- (2-methoxyethoxy) methoxy-4 (S)-[N- (4-cyanophenylcarbonyl) amino] pentanoic acid, (63) 2 (R)-(2-methoxyethoxy) ) Methyl-5-ethoxymethoxy-4
(S)-[N- (4-nitrophenylcarbonyl) amino] pentanoic acid, (65) 2 (S) -allyl-5- (2-
Methoxyethoxy) methoxy-4 (S)-[N- (4-
(Cyanophenylcarbonyl) amino] pentanoic acid, (66)
2 (S) -methoxymethyl-5- (2-methoxyethoxy) methoxy-4 (S)-[N- (4-cyanophenylcarbonyl) amino] pentanoic acid, (69) 2 (R)-
Methoxymethyl-5-ethoxymethoxy-4 (S)-
[N- (4-bromophenylcarbonyl) amino] pentanoic acid, (70) 2 (R) -methoxymethyl-5-ethoxymethoxy-4 (S)-[N- (4-chlorophenylcarbonyl) amino] pentanoic acid, (71) 2 (R) -benzyloxymethyl-5- (2-methoxyethoxy) methoxy-4 (S)-[N- (4-cyanophenylcarbonyl) amino] pentanoic acid, (72) 2 (R)- Benzyloxymethyl-5-ethoxymethoxy-4 (S)-[N-
(4-chlorophenylcarbonyl) amino] pentanoic acid, (73) 2 (R) -benzyloxymethyl-5-ethoxymethoxy-4 (S)-[N- (4-bromophenylcarbonyl) amino] pentanoic acid, (74 ) 2 (S) -allyl-5-ethoxymethoxy-4 (S)-[N- (4-
Bromophenylcarbonyl) amino] pentanoic acid, (75)
2 (S) -allyl-5-ethoxymethoxy-4 (S)
-[N- (4-chlorophenylcarbonyl) amino] pentanoic acid, (76) 2 (R)-(2-methoxyethoxy)
Methyl-5-ethoxymethoxy-4 (S)-[N- (4
-Bromophenylcarbonyl) amino] pentanoic acid, (7
7) 2 (R)-(2-methoxyethoxy) methyl-5
(2-methoxyethoxy) methoxy-4 (S)-[N-
(4-cyanophenylcarbonyl) amino] pentanoic acid, (78) 2 (R)-(2-methoxyethoxy) methyl-5-ethoxymethoxy-4 (S)-[N- (4-chlorophenylcarbonyl) amino] pentane Acid, (80) 2
(S) -methyl-5-ethoxymethoxy-4 (S)-
[N-methyl-N- (4-bromophenylcarbonyl)
Amino] pentanoic acid, (81) 2 (S) -methyl-5-ethoxymethoxy-4 (S)-[N-methyl-N- (4-
Nitrophenylcarbonyl) amino] pentanoic acid, (82)
2 (S) -benzyl-4 (S) -t-butyldimethylsilyloxymethyl-4- (N- (4- (benzofuran-2-yl) phenylcarbonyl) amino) butanoic acid,
(83) 2 (R) -benzyl-4 (S) -hydroxymethyl-4- (N- (4- (benzofuran-2-yl) phenylcarbonyl) amino) butanoic acid, (84) 2 (S)-
Benzyl-4 (S) -hydroxymethyl-4- (N-
(4- (3-Methoxy-1-propynyl) phenylcarbonyl) amino) butanoic acid, (85) 2 (S) -benzyloxy-3 (S) -hydroxy-4- (N- (4- (3
-Methoxy-1-propynyl) phenylcarbonyl) amino) butanoic acid, (86) 2-benzyloxy-4- (N
-(4- (3-methoxy-1-propynyl) phenylcarbonyl) amino) -2-butenoic acid, (87) cis-1-
Carboxymethyl-2- (N- (4- (3-methoxy-
1-propynyl) phenylcarbonyl) amino) cyclopentane, (88) trans-1-carboxymethyl-2
-(N- (4- (3-methoxy-1-propynyl) phenylcarbonyl) amino) cyclopentane, (89) trans-3- (N- (4- (3-methoxy-1-propynyl) phenylcarbonyl) amino ) Cyclopentanoic acid,
(90) cis-3- (N- (4- (3-methoxy-1-propynyl) phenylcarbonyl) amino) cyclopentanoic acid, (91) trans-2- (N- (4- (3-methoxy-1 -Propynyl) phenylcarbonyl) aminomethyl) cyclopentanoic acid, (92) 2 (R) -allyl-5
Ethoxymethoxy-4 (S)-[N- (4-phenoxyphenylcarbonyl) amino] pentanoic acid, (93) 5-
Methoxy-4 (S)-[N- [4- (4-chlorophenyl) phenylcarbonyl] amino] pentanoic acid, (94)
2 (S) -methyl-5-succinimide-4 (S)-
[N- (4-chlorophenylcarbonyl) amino] pentanoic acid, (95) 2 (S) -methyl-5-ethoxymethoxy-4 (S)-[N- (4-phenoxyphenylcarbonyl) amino] pentanoic acid, 96) 2 (S) -allyl-
5-ethoxymethoxy-4 (S)-[N- (4-phenoxyphenylcarbonyl) amino] pentanoic acid, (97)
2 (S) -methyl-5-ethoxymethoxy-4 (S)-
The compound according to claim 2, which is [N- [4- (4-cyanophenyl) phenylcarbonyl] amino] pentanoic acid, a methyl ester, an ethyl ester, a t-butyl ester thereof, or a non-toxic salt thereof. 10. The compound according to claim 1, wherein (1) N-hydroxy-4
-(N- (4- (benzofuran-2-yl) phenylca
Rubonyl) amino) butyramide, (2) N-hydroxy
-4- (N- (4-methylphenylcarbonyl) amido
(N) butyramide, (3) N-hydroxy-4- (N-
(4-butyloxyphenylcarbonyl) amino) buty
Lamide, (4) N-hydroxy-4- (N- (3-butyi)
Ruoxyphenylcarbonyl) amino) butyramide,
(5) N-hydroxy-4- [N- [4-((4-methyl
Ruphenyl) ethynyl) furan-2-ylcarbonyl]
Amino] butyramide, do, (6) N-hydroxy-4-
(N- (4- (pyrrole-1-yl) phenylcarbonyl)
Ru) amino) butyramide, (7) N-hydroxy-4-
(N- (trans-4-methylcyclohexylcarboni
Ru) amino) butyramide, (8) N-hydroxy-4-
(N- (4- (3-methoxy-1-propynyl) phenyi)
Lecarbonyl) amino) butyramide, (9) N-hydro
Xy-4- (N- (4-butylphenylcarbonyl) a
Mino) butyramide, (10) N-hydroxy-4- (N-
(Benzofuran-2-ylcarbonyl) amino) butyra
Mido, (11) N-hydroxy-4- [N- [4- (2-
(4-chlorophenyl) ethenyl) phenylcarboni
L] amino] butyramide, (12) N-hydroxy-4-
[N- [4-((4- (imidazol-1-yl) fe
Nyl) ethynyl) phenylcarbonyl] amino] butyra
Mido, (13) N-hydroxy-4- (N- (trans-
4-propylcyclohexylcarbonyl) amino) buty
Lamide, (14) N-hydroxy-4- [N- [4-
((4-methylphenyl) ethynyl) phenylcarboni
L] amino] butyramide, (15) N-hydroxy-4-
[N- [4-((4-bromophenyl) aminosulfoni
L) phenylcarbonyl] amino] butyramide, (16)
N-hydroxy-4- [N- (4-cyclohexylfe)
Nylcarbonyl) amino] butyramide, (17) N-hydrido
Roxy-4- [N- [4- (4-propylphenyl) phenyl
Phenylcarbonyl] amino] butyramide, (18) N-
Droxy-4- [N- [4- (4-hydroxyphenyl)
Ru) phenylcarbonyl] amino] butyramide, (19)
N-hydroxy-4- [N- [4- (4-chlorophenyl
Le) Furan-2-ylcarbonyl] amino] butyralami
, (20) N-hydroxy-4- [N- [4- (4-
Butylphenyl) phenylcarbonyl] amino] butyra
Mido, (21) N-hydroxy-4- [N- [4- (4-
Methoxyphenyl) phenylcarbonyl] amino] buty
Lamide, (22) N-hydroxy-4- [N- [4- (4
-Chlorophenyl) phenylcarbonyl] amino] buty
Lamide, (23) N-hydroxy-4- [N- (5-ben
Diloxindol-2-ylcarbonyl) amino]
Butyramide, (24) N-hydroxy-4- [N- [5-
(2- (4-chlorophenyl) ethenyl) furan-2-
Ylcarbonyl] amino] butyramide, (25) N-hydrido
Roxy-4- [N- (4-phenoxyphenylcarboni
Ru) amino] butyramide, (28) N-hydroxy-4-
[N-[[(4'-carbamoylmethoxy) biphenyl
-4-yl] carbonyl] amino] butyramide, (29)
N-hydroxy-4- [N- [4- (4-phenylpipe
Lysin-1-yl) phenylcarbonyl] amino] buty
Lamide, (30) N-hydroxy-4- [N- [4- [3
-(4-Chlorophenoxy) -1-propynyl] phenyi
[Carbonyl] amino] butyramide, (31) N-hydro
Xy-4- [N- [4- (3-phenoxy-1-propy
Nyl) phenylcarbonyl] amino] butyramide, (32)
N-hydroxy-4- [N- [4- (4-methoxy
Enoxy) phenylcarbonyl] amino] butyramide,
(33) N-hydroxy-4- [N- [4- (4-hydro
Xyphenoxy) phenylcarbonyl] amino] butyra
Mido, (34) N-hydroxy-4- [N- [4- (4-
Phenoxypiperazin-1-yl) phenylcarboni
[Amino] butyramide, (35) N-hydroxy-4-
[N- [4- (4-phenyl-1,2,5,6-tetra
Hydropyridin-1-yl) phenylcarbonyl] amido
No] butyramide, (36) N-hydroxy-4- [N-
[4- (1-Heptynyl) phenylcarbonyl] amido
No] butyramide, (37) N-hydroxy-4- [N-
(4-benzyloxyphenylcarbonyl) amino] butane
Tyramide, (38) N-hydroxy-4- (N-methyl-
N- (4- (benzofuran-2-yl) phenylcarbo
Nyl) amino) butyramide, (39) N-hydroxy-4
-(N- (4- (benzofuran-2-yl) phenylca
Rubonyl) amino) -2 (S) -hydroxybutyrami
, (40) N-hydroxy-4- (N- (4- (benzo
Furan-2-yl) phenylcarbonyl) amino) -2
(R) -hydroxybutyramide, (41) N-hydroxy
-4- (N- (4- (benzofuran-2-yl) phenyl)
Carbonyl) amino) -2 (S) -benzyloxime
Toxibutyramide, (42) N-hydroxy-4- (N-
(4- (benzofuran-2-yl) phenylcarboni
Ru) amino) -2 (R) -benzyloxymethoxybuty
Lamide, (43) N-hydroxy-4- (N- (4- (2
-(4-chlorophenyl) ethenyl) phenylcarbonyl
Ru) amino) -2 (S) -benzyloxymethoxybuty
Lamide, (44) N-hydroxy-4- (N- (4-chloro
Rophenylcarbonyl) amino) -2-benzyloxy
Methoxybutyramide, (45) N-hydroxy-4- (N
-(4-chlorophenylcarbonyl) amino) -2-
((N-benzyl-N-methylamino) carbonylmetho
Xy) butyramide, (46) N-hydroxy-4- (N-
(4-chlorophenylcarbonyl) amino) -2-
((N-phenyl-N-methylamino) carbonylmetho
Xy) butyramide, (47) N-hydroxy-4- (N-
(4-chlorophenylcarbonyl) amino) -2-
((N-phenylethyl-N-methylamino) carboni
Rumethoxy) butyramide, (48) N-hydroxy-3
(S) -hydroxy-4- (N- (4- (benzofuran
-2-yl) phenylcarbonyl) amino) butyrami
(49) N-hydroxy-3 (R) -hydroxy-4
-(N- (4- (benzofuran-2-yl) phenylca
Rubonyl) amino) butyramide, (50) N-hydroxy
-3 (S) -methoxymethyloxy-4- (N- (4-
(Benzofuran-2-yl) phenylcarbonyl) amido
(No) butyramide, (51) N-hydroxy-4- (N-
(4- (benzofuran-2-yl) phenylcarboni
L) amino) -2-butenamide, (52) N-hydroxy
C-3 (R) -methoxymethyloxy-4- (N- (4
-(Benzofuran-2-yl) phenylcarbonyl) a
Mino) butyramide, (53) N-hydroxy-4- (N-
(4- (benzofuran-2-yl) phenylcarboni
L) amino) -3-butenamide, (54) N-hydroxy
C-4- [N- [4- (benzofuran-2-yl) fe
Nylcarbonyl] amino] -3 (S) -benzyloxy
Methoxybutyramide, (55) N-hydroxy-2-ben
Ziroxymethyl-4- (N- (4-methylphenylca
Rubonyl) amino) butyramide, (56) N-hydroxy
-2 (RS) -hydroxymethyl-4- (N- (4-meth
Tylphenylcarbonyl) amino) butyramide, (57)
N-hydroxy-2 (R) -hydroxymethyl-4-
(N- (4-methylphenylcarbonyl) amino) buty
Lamide, (58) N-hydroxy-2 (S) -hydroxy
Methyl-4- (N- (4-methylphenylcarbonyl)
Amino) butyramide, (59) N-hydroxy-4 (S)
-Methylaminocarbonyl-4- (N- (4-methylf
Enylcarbonyl) amino) butyramide, (60)
Droxy-4 (R) -methylaminocarbonyl-4-
(N- (4-methylphenylcarbonyl) amino) buty
Lamide, (61) N-hydroxy-4 (S) -benzyla
Minocarbonyl-4- (N- (4-methylphenylcar
Bonyl) amino) butyramide, (62) N-hydroxy-
4 (S)-(4-hydroxybutyl) aminocarbonyl
-4- (N- (4-methylphenylcarbonyl) amido
G) Butyramide, (63) N-hydroxy-4 (S) -meth
Toxycarbonyl-4- [N- [4- (4-hydroxy
-1-butynyl) phenylcarbonyl] amino] butyra
Mido, (64) N-hydroxy-4 (R) -carbonyl-
4- [N- [4- (3-methoxy-1-propynyl) phenyl
Enylcarbonyl] amino] butyramide, (65)
Droxy-4 (S) -carboxy-4- (N- (4-meth
Tylphenylcarbonyl) amino) butyramide, (66)
N-hydroxy-4 (S)-(morpholin-1-yl)
Carbonyl-4- (N- (4- (benzofuran-2-i
Ru) phenylcarbonyl) amino) butyramide, (67)
N-hydroxy-4 (S) -hydroxymethyl-4-
(N- (4- (benzofuran-2-yl) phenylcal
Bonyl) amino) butyramide, (68) N-hydroxy-
4 (S) -methoxymethyloxymethyl-4- (N-
(4- (benzofuran-2-yl) phenylcarboni
Ru) amino) butyramide, (69) N-hydroxy-2
(S) -benzyl-4 (S) -methoxymethyloxime
Tyl-4- (N- (4- (benzofuran-2-yl) phenyl
Enylcarbonyl) amino) butyramide, (70)
Droxy-2 (S) -methyl-4 (S) -methoxymethyl
Roxymethyl-4- (N- (4- (benzofuran-2
-Yl) phenylcarbonyl) amino) butyramide, (7
1) N-hydroxy-2 (S)-(3-phenyl-2-
Propenyl) -4 (S) -methoxymethyloxymethyl
-4- (N- (4- (benzofuran-2-yl) phenyl)
Carbonyl) amino) butyramide, (72) N-hydro
Xy-2 (S)-(3-phenylpropyl) -4 (S)
-Methoxymethyloxymethyl-4- (N- (4- (
Nzofuran-2-yl) phenylcarbonyl) amino)
Butyramide, (73) N-hydroxy-2 (R) -benzyl
-4 (S) -hydroxymethyl-4- (N- (4-
(Benzofuran-2-yl) phenylcarbonyl) amido
G) butyramide, (74) N-hydroxy-2 (S)-
Benzyl-4 (S) -hydroxymethyl-4- (N- (4
-(3-methoxy-1-propynyl) phenyl carbonyl
Ru) amino) butyramide, (75) N-hydroxy-5-
Hydroxy-4 (S)-[N- [4- (3-methoxy-
1-propynyl) phenylcarbonyl] amino] penta
Amide, (76) N-hydroxy-5-hydroxy-4
(R)-[N- [4- (3-methoxy-1-propini)
Ru) phenylcarbonyl] amino] pentanamide, (7
7) N-hydroxy-4 (S)-(4-hydroxybutyi)
Rucarbamoyl) -4- [N- [4- (3-methoxy-
1-propynyl) phenylcarbonyl] amino] butyra
Mido, (78) N-hydroxy-4 (S)-(3-phenyl
Propylcarbamoyl) -4- [N- [4- (3-meth
Toxi-1-propynyl) phenylcarbonyl] amido
No] butyramide, (79) N-hydroxy-4 (S) -p
Ropyrcarbamoyl-4- [N- [4- (3-methoxy
-1-propynyl) phenylcarbonyl] amino] buty
Lamide, (80) N-hydroxy-4 (S)-(2-hydr
Roxyethylcarbamoyl) -4- [N- [4- (3-
Methoxy-1-propynyl) phenylcarbonyl] amido
No] butyramide, (81) N-hydroxy-4 (S)-
(6-hydroxyhexylcarbamoyl) -4- [N-
[4- (3-methoxy-1-propynyl) phenylcar
Bonyl] amino] butyramide, (82) N-hydroxy-
4 (S)-[2- (4-methoxyphenyl) ethylcal
Bamoyl] -4- [N- [4- (3-methoxy-1-p)
Lopinyl) phenylcarbonyl] amino] butyramide,
(83) N-hydroxy-4 (S)-(2-morpholinoe
Tylcarbamoyl) -4- [N- [4- (3-methoxy
-1-propynyl) phenylcarbonyl] amino] buty
Lamide, (84) N-hydroxy-4 (S)-[2- (a
Ndol-3-yl) ethylcarbamoyl) -4- [N
-[4- (3-methoxy-1-propynyl) phenylca
Rubonyl] amino] butyramide, (85) N-hydroxy
-4 (S)-(4-phenylbutylcarbamoyl) -4
-[N- [4- (3-methoxy-1-propynyl) fe
Nylcarbonyl] amino] butyramide, (86) N-hydrido
Roxy-4 (S)-(2-phenylethylcarbamoy
) -4- [N- [4- (3-methoxy-1-propini)
Ru) phenylcarbonyl] amino] butyramide, (87)
N-hydroxy-4 (S)-[3- (pyrazole-1-
Yl) propylcarbamoyl] -4- [N- [4- (3
-Methoxy-1-propynyl) phenylcarbonyl] a
Mino] butyramide, (88) N-hydroxy-4 (R)-
(3-phenylpropylcarbamoyl) -4- [N-
[4- (3-methoxy-1-propynyl) phenylcar
Bonyl] amino] butyramide, (89) N-hydroxy-
2- (pyridin-3-yl) methyl-4- (2-phenyl
Ruethylcarbamoyl) -4- [N- (4-phenoxy
Phenylcarbonyl) amino] butyramide, (90) N-
Hydroxy-5-methoxymethoxy-4 (S)-[N-
[4- (3-methoxy-1-propynyl) phenylcar
Bonyl] amino] pentanamide, (91) N-hydroxy
C-5-benzyloxymethoxy-4 (S)-[N-
[4- (3-methoxy-1-propynyl) phenylcar
Bonyl] amino] pentanamide, (92) N-hydroxy
C-5- (2-methoxyethoxy) methoxy-4 (S)
-[N- [4- (3-phenoxy-1-propynyl) phenyl
Enylcarbonyl] amino] pentanamide, (93) N
-Hydroxy-5-methoxymethoxy-4 (S)-[N
-[4- (3-phenoxy-1-propynyl) phenyl
Carbonyl] amino] pentanamide, (94) N-hydrido
Roxy-5-benzyloxymethoxy-4 (S)-[N
-[4- (3-phenoxy-1-propynyl) phenyl
Carbonyl] amino] pentanamide, (95) N-hydrido
Roxy-5-methoxymethoxy-4 (S)-[N- (4
-Phenoxyphenylcarbonyl) amino] pentana
Mido, (96) N-hydroxy-5-methoxymethoxy-
4 (S)-[N- [4- (4-chlorophenyl) phenyl
Carbonyl] amino] pentanamide, (97) N-
Droxy-5-methoxymethoxy-4 (S)-[N-
[4- [2- (4-methylphenyl) ethynyl] phenyl
[Carbonyl] amino] pentanamide, (98) N-hi
Droxy-5-methoxymethoxy-4 (S)-[N-
[4- [2E- (4-chlorophenyl) ethenyl] fe
Nylcarbonyl] amino] pentanamide, (99) N-
Hydroxy-5-methoxymethoxy-4 (S)-[N-
[4- (1-Heptynyl) phenylcarbonyl] amido
No] pentanamide, (100) N-hydroxy-5-e
Toxymethoxy-4 (S)-[N- (4-phenoxyf
Enylcarbonyl) amino] pentanamide, (101)
N-hydroxy-5-ethoxymethoxy-4 (S)-
[N- (4-methylphenylcarbonyl) amino] pen
Tanamide, (102) N-hydroxy-5-methoxymeth
Toxic-4 (R)-[N- [4- (3-methoxy-1-
Propynyl) phenylcarbonyl] amino] pentana
Mido, (103) N-hydroxy-2 (S) -methyl-5
-Methoxymethoxy-4 (S)-[N- [4- [2-
(4-imidazolylphenyl) ethynyl] phenylcar
Bonyl] amino] pentanamide, (104) N-hydro
Xy-2 (S) -methyl-5-methoxymethoxy-4
(S)-[N- [4- (4-phenyl-1,2,5,6
-Tetrahydropyridin-1-yl) phenylcarboni
[Amino] pentanamide, (105) N-hydroxy
-2 (S) -methyl-5-methoxymethoxy-4 (S)
-[N- (4-phenoxyphenylcarbonyl) amido
No] pentanamide, (106) N-hydroxy-2
(S) -methyl-5-methoxymethoxy-4 (S)-
[N- [4- [2- (4-chlorophenyl) ethenyl]
Phenylcarbonyl] amino] pentanamide, (107)
N-hydroxy-2 (S) -methyl-5-methoxymeth
Toxic-4 (S)-[N- [4- (4-propylphenyl)
Ru) phenylcarbonyl] amino] pentanamide, (1
08) N-hydroxy-2 (S) -methyl-5-methoxy
Cymethoxy-4 (S)-[N- [4- (benzothiophene
N-2-yl) phenylcarbonyl] amino] pentane
Amide, (109) N-hydroxy-2 (S) -methyl-
5-methoxymethoxy-4 (S)-[N- [4- (3-
Methoxyphenoxy) phenylcarbonyl] amino] pe
Tantanamide, (110) N-hydroxy-2 (S) -meth
Tyl-5-methoxymethoxy-4 (S)-[N- [4-
(4-methoxyphenoxy) phenylcarbonyl] ami
No] pentanamide, (111) N-hydroxy-2
(S) -methyl-5-methoxymethoxy-4 (S)-
[N- (4-benzoylphenylcarbonyl) amino]
Pentanamide, (112) N-hydroxy-2 (S)-
Methyl-5-methoxymethoxy-4 (S)-[N- [4
-(Naphthalen-2-yl) phenylcarbonyl] ami
No] pentanamide, (113) N-hydroxy-2
(S) -methyl-5-methoxymethoxy-4 (S)-
[N- [4-[(4-methoxybiphenyl-4′-i
L) oxy] phenylcarbonyl] amino] pentana
Mido, (114) N-hydroxy-2 (S) -methyl-5
-Methoxymethoxy-4 (S)-[N- [4- (4-E
Toxiphenyl) phenylcarbonyl] amino] penta
Amide, (115) N-hydroxy-2 (S) -methyl
-5-methoxymethoxy-4 (S)-[N- [4- (4
-Phenoxyphenyl) phenylcarbonyl] amino]
Pentanamide, (116) N-hydroxy-2 (S)-
Methyl-5-methoxymethoxy-4 (S)-[N- [4
-(3-cyanomethylphenyl) phenylcarbonyl]
Amino] pentanamide, (117) N-hydroxy-2
(S) -methyl-5-methoxymethoxy-4 (S)-
[N- [4- (biphenyl-4-yl) phenylcarbo
Nyl] amino] pentanamide, (118) N-hydroxy
C-2 (S) -methyl-5-methoxymethoxy-4
(S)-[N- [4- (3-hydroxyphenoxy) phenyl
[Enylcarbonyl] amino] pentanamide, (119)
N-hydroxy-2 (S) -methyl-5-methoxymeth
Xy-4 (S)-[N- [4- [2- (4-methylphen
Nyl) ethynyl] phenylcarbonyl] amino] penta
Amido, (120) N-hydroxy-2 (S) -methyl
-5-methoxymethoxy-4 (S)-[N- [4- (4
-Hydroxyphenoxy) phenylcarbonyl] amido
No] pentanamide, (121) N-hydroxy-2
(S) -methyl-5-methoxymethoxy-4 (S)-
[N- [4- (4-chlorophenyl) phenylcarbonyl]
[Amino] pentanamide, (122) N-hydroxy
-2 (S) -methyl-5-methoxymethoxy-4 (S)
-[N-[[5- (4-methoxyphenyl) -2-thiene
Nyl] carbonyl] amino] pentanamide, (123)
N-hydroxy-2 (S) -methyl-5-methoxymeth
Xy-4 (S)-[N- [4-[(biphenyl-3-i
L) oxy] phenylcarbonyl] amino] pentana
Mido, (124) N-hydroxy-2 (S) -methyl-5
-Methoxymethoxy-4 (S)-[N- [4- (1-to
Butynyl) phenylcarbonyl] amino] pentanami
, (125) N-hydroxy-2 (S) -methyl-5-
Methoxymethoxy-4 (S)-[N- [4- (3-fe
Nonoxy-1-propynyl) phenylcarbonyl] ami
No] pentanamide, (126) N-hydroxy-2
(S) -methyl-5-methoxymethoxy-4 (S)-
[N- [4- (4-cyanophenyl) phenylcarbonyl]
[Amino] pentanamide, (127) N-hydroxy
-2 (S) -methyl-5-methoxymethoxy-4 (S)
-[N- [4- (3-cyanophenyl) phenylcarbo
Nyl] amino] pentanamide, (128) N-hydroxy
C-2 (S) -methyl-5-methoxymethoxy-4
(S)-[N- (4-benzylphenylcarbonyl) a
Mino] pentanamide, (129) N-hydroxy-2
(S) -methyl-5-methoxymethoxy-4 (S)-
[N- [4- [2E- (pyridin-4-yl) etheni
[Phenylphenyl] amino] pentanamide, (1
30) N-hydroxy-2 (S) -methyl-5-methoxy
Cymethoxy-4 (S)-[N- [4- (benzoxazo
2-yl) phenylcarbonyl] amino] penta
Amido, (131) N-hydroxy-2 (S) -methyl
-5-methoxymethoxy-4 (S)-[N- [4- (3
-Ethoxyphenyl) phenylcarbonyl] amino] pe
Tantanamide, (132) N-hydroxy-2 (S) -me
Tyl-5-methoxymethoxy-4 (S)-[N- [4-
(4-methylphenylcarbonylamino) phenylcar
Bonyl] amino] pentanamide, (133) N-hydro
Xy-2 (S) -methyl-5-methoxymethoxy-4
(S)-[N-[[5- [2- (4-methylphenyl)
Ethynyl] -2-thienyl] carbonyl] amino] pen
Tanamide, (134) N-hydroxy-2 (S) -methyl
Ru-5- (2-methoxyethoxy) methoxy-4 (S)
-[N- (4-phenoxyphenylcarbonyl) amido
No] pentanamide, (135) N-hydroxy-2
(S) -methyl-5-t-butylcarbonyloxy-4
(S)-[N- (4-phenoxyphenylcarbonyl)
Amino] pentanamide, (136) N-hydroxy-2
(S) -methyl-5-benzyloxymethoxy-4
(S)-[N- (4-phenoxyphenylcarbonyl)
Amino] pentanamide, (137) N-hydroxy-2
(S) -methyl-5-ethoxymethoxy-4 (S)-
[N- (trans-4-methylcyclohexylcarbonyl)
Ru) amino] pentanamide, (138) N-hydroxy
-2 (S) -methyl-5-ethoxymethoxy-4 (S)
-[N- (4-methylphenylcarbonyl) amino] pe
Tantanamide, (139) N-hydroxy-2 (S) -me
Tyl-5-ethoxymethoxy-4 (S)-[N- (4-
Chlorophenylcarbonyl) amino] pentanamide,
(140) N-hydroxy-2 (S) -methyl-5-etho
Xymethoxy-4 (S)-[N- (adamantylcarbo
Nyl) amino] pentanamide, (141) N-hydroxy
C-2 (S) -methyl-5-ethoxymethoxy-4
(S)-[N- (2-furylcarbonyl) amino] pen
Tanamide, (142) N-hydroxy-2 (S) -methyl
Ru-5-ethoxymethoxy-4 (S)-[N-[(ben
Zothiazol-6-yl) carbonyl] amino] penta
Amide, (143) N-hydroxy-2 (S) -methyl
-5-ethoxymethoxy-4 (S)-[N- (4-fur
Orophenylcarbonyl) amino] pentanamide, (1
44) N-Hydroxy-2 (S) -methyl-5-ethoxy
Cymethoxy-4 (S)-[N-[(2-bromofuryl-
5-yl) carbonyl] amino] pentanamide, (14
5) N-hydroxy-2 (S) -methyl-5-ethoxy
Methoxy-4 (S)-[N- (4-nitrophenylcarb
Bonyl) amino] pentanamide, (146) N-hydro
Xy-2 (S) -methyl-5-ethoxymethoxy-4
(S)-[N- (4-bromophenylcarbonyl) amido
No] pentanamide, (147) N-hydroxy-2
(S) -methyl-5-ethoxymethoxy-4 (S)-
[N- (4-cyanophenylcarbonyl) amino] pen
Tanamide, (148) N-hydroxy-2 (S) -methyl
Ru-5-ethoxymethoxy-4 (S)-[N- [4-
(4-pyridyloxy) phenylcarbonyl] amino]
Pentanamide, (149) N-hydroxy-2 (S)-
Methyl-5- (2-methoxyethoxy) methoxy-4
(S)-[N- (4-cyanophenylcarbonyl) amido
No] pentanamide, (150) N-hydroxy-2
(S) -methyl-5-methoxymethoxy-4 (S)-
[N- (4-chlorophenylcarbonyl) amino] pen
Tanamide, (151) N-hydroxy-2 (S) -methyl
5-benzyloxymethoxy-4 (S)-[N-
(4-Chlorophenylcarbonyl) amino] pentana
Mido, (152) N-hydroxy-2 (S) -methyl-5
-(2-methoxyethoxy) methoxy-4 (S)-[N
-(4-Chlorophenylcarbonyl) amino] pentane
Amide, (153) N-hydroxy-2 (S) -methyl-
5-ethoxymethoxy-4 (S)-[N- (2-nitro
Phenylcarbonyl) amino] pentanamide, (154)
N-hydroxy-2 (S) -methyl-5-ethoxyme
Toxic-4 (S)-[N- (3-nitrophenylcarbo
Nyl) amino] pentanamide, (155) N-hydroxy
C-2 (S) -methyl-5-ethoxymethoxy-4
(S)-[N- (2-methoxy-4-nitrophenylca)
Rubonyl) amino] pentanamide, (156) N-hydrido
Roxy-2 (S) -methyl-5-ethoxymethoxy-4
(S)-[N- (3-methoxy-4-nitrophenylca)
Rubonyl) amino] pentanamide, (157) N-hydrido
Roxy-2 (S) -methyl-5-ethoxymethoxy-4
(S)-[N- (3-hydroxy-4-nitrophenyl
Carbonyl) amino] pentanamide, (158) N-
Droxy-2 (S) -methyl-5-ethoxymethoxy-
4 (S)-[N- (4-dihydroxyboronylphenyl
Carbonyl) amino] pentanamide, (159)
Droxy-2 (S) -isobutyl-5-methoxymethoxy
C-4 (S)-[N- (4-phenoxyphenylcarbo
Nyl) amino] pentanamide, (160) N-hydroxy
C-2 (S) -ethyl-5-methoxymethoxy-4
(S)-[N- (4-phenoxyphenylcarbonyl)
Amino] pentanamide, (161) N-hydroxy-2
(S) -propyl-5-methoxymethoxy-4 (S)-
[N- (4-phenoxyphenylcarbonyl) amino]
Pentanamide, (162) N-hydroxy-2 (R)-
t-butoxycarbonylmethyl-5-methoxymethoxy
-4 (S)-[N- (4-phenoxyphenylcarboni
Ru) amino] pentanamide, (163) N-hydroxy
-2 (S) -allyl-5-methoxymethoxy-4 (S)
-[N- (4-phenoxyphenylcarbonyl) amido
No] pentanamide, (164) N-hydroxy-2
(S) -ethyl-5-ethoxymethoxy-4 (S)-
[N- (4-phenoxyphenylcarbonyl) amino]
Pentanamide, (165) N-hydroxy-2 (S)-
Ethyl-5- (2-methoxyethoxy) methoxy-4
(S)-[N- (4-phenoxyphenylcarbonyl)
Amino] pentanamide, (166) N-hydroxy-2
(S) -ethyl-5-t-butylcarbonyloxy-4
(S)-[N- (4-phenoxyphenylcarbonyl)
Amino] pentanamide, (167) N-hydroxy-2
(S) -allyl-5-ethoxymethoxy-4 (S)-
[N- (4-methylphenylcarbonyl) amino] pen
Tanamide, (168) N-hydroxy-2 (S) -ant
Ru-5-ethoxymethoxy-4 (S)-[N- (4-d
Trophenylcarbonyl) amino] pentanamide, (1
69) N-hydroxy-2-methylidene-5-ethoxy
Methoxy-4 (S)-[N- (4-nitrophenylcarb
Bonyl) amino] pentanamide, (171) N-hydro
Xy-2 (S) -allyl-5- (2-methoxyethoxy
B) methoxy-4 (S)-[N- (4-cyanophenyl
Carbonyl) amino] pentanamide, (174)
Droxy-2 (S) -allyl-5-ethoxymethoxy-
4 (S)-[N- (4-bromophenylcarbonyl) a
Mino] pentanamide, (175) N-hydroxy-2
(S) -allyl-5-ethoxymethoxy-4 (S)-
[N- (4-chlorophenylcarbonyl) amino] pen
Tanamide, (176) N-hydroxy-2 (R) -dim
Tylaminomethyl-5-ethoxymethoxy-4 (S)-
[N- (4-nitrophenylcarbonyl) amino] pen
Tanamide, (178) N-hydroxy-2 (R) -ben
Jil-5-methoxymethoxy-4 (R)-[N- (4-
Phenoxyphenylcarbonyl) amino] pentanami
, (179) N-hydroxy-2 (R) -benzyl-5
-Methoxymethoxy-4 (R)-[N- [4- (3-f
Enoxy-1-propynyl) phenylcarbonyl] amido
No] pentanamide, (180) N-hydroxy-2
(R) -methyl-5-ethoxymethoxy-4 (R)-
[N- [4- (4-cyanophenyl) phenylcarbonyl]
[Amino] pentanamide, (181) N-hydroxy
-2 (R) -allyl-5-ethoxymethoxy-4 (R)
-[N- (4-phenoxyphenylcarbonyl) amido
No] pentanamide, (182) N-hydroxy-2
(R) -methyl-5-ethoxymethoxy-4 (R)-
[N- (4-phenoxyphenylcarbonyl) amino]
Pentanamide, (183) N-hydroxy-2 (S)-
Benzyl-5-methoxymethoxy-4 (S)-[N-
[4- [2E- (4-chlorophenyl) ethenyl] fe
Nylcarbonyl] amino] pentanamide, (184) N
-Hydroxy-2 (S)-(indol-3-yl)-
5-methoxymethoxy-4 (S)-[N- [4- (ben
Zofuran-2-yl) phenylcarbonyl] amino] pe
Tantanamide, (185) N-hydroxy-2 (S)-
Benzyl-5-methoxymethoxy-4 (S)-[N- [4
-[3- (4-chlorophenoxy-1-propynyl) phenyl
[Enylcarbonyl] amino] pentanamide, (186)
N-hydroxy-2 (S) -benzyl-5-methoxymeth
Toxic-4 (S)-[N- (4-phenoxyphenylca
Rubonyl) amino] pentanamide, (187) N-hydrido
Roxy-2 (S) -benzyl-5-methoxymethoxy-
4 (S)-[N- [4- (4-phenylpiperidine-1
-Yl) phenylcarbonyl] amino] pentanami
, (188) N-hydroxy-2 (S) -benzyl-5
-Methoxymethoxy-4 (S)-[N- [4- (6-i
Midazolyl-1-hexynyl) phenylcarbonyl] a
Mino] pentanamide, (189) N-hydroxy-2
(S)-(Naphthalen-1-yl) -5-methoxymeth
Xy-4 (S)-[N- (4-phenoxyphenylcar
Bonyl) amino] pentanamide, (190) N-hydro
Xy-2 (S)-[4- (benzofuran-2-yl) be
Ndyl] -5-methoxymethoxy-4 (S)-[N-
(4-Iodophenylcarbonyl) amino] pentana
Mido, (191) N-hydroxy-2 (S) -benzyl-
5-ethoxymethoxy-4 (S)-[N- (trans-
4-methylcyclohexylcarbonyl) amino] penta
Amide, (192) N-hydroxy-2 (S)-(4-
Nitrobenzyl) -5-ethoxymethoxy-4 (S)-
[N- (trans-4-methylcyclohexylcarbonyl)
Ru) amino] pentanamide, (193) N-hydroxy
-2 (S)-(indol-3-yl) -5-ethoxy
Methoxy-4 (S)-[N- (trans-4-methylsi
Clohexylcarbonyl) amino] pentanamide, (1
94) N-hydroxy-2 (S) -benzyl-5-ethoxy
Xymethoxy-4 (S)-[N-[(pyridine-4-i
Ru) carbonyl] amino] pentanamide, (195) N
-Hydroxy-2 (S) -benzyl-5-ethoxymethoate
Xy-4 (S)-[N- (4-hydroxyphenylcar
Bonyl) amino] pentanamide, (196) N-hydro
Xy-2 (S)-(2-nitrobenzyl) -5-ethoxy
Cymethoxy-4 (S)-[N- (trans-4-methyl
Cyclohexylcarbonyl) amino] pentanamide,
(197) N-hydroxy-2 (S)-(3-nitroben
Zyl) -5-ethoxymethoxy-4 (S)-[N- (g
Lance-4-methylcyclohexylcarbonyl) amido
No] pentanamide, (198) N-hydroxy-2
(S) -benzyl-5-ethoxymethoxy-4 (S)-
[N-[(1-methylpyrrole-2-yl) carbonyl]
[Amino] pentanamide, (199) N-hydroxy
-2 (S) -benzyl-5-ethoxymethoxy-4
(S)-[N- (phenylcarbonyl) amino] penta
Amide, (200) N-hydroxy-2 (S) -benzyl
Ru-5-ethoxymethoxy-4 (S)-[N- (4-ethoxy
Tylphenylcarbonyl) amino] pentanamide, (2
01) N-hydroxy-2 (S) -benzyl-5-etho
Xymethoxy-4 (S)-[N- (4-methylphenyl
Carbonyl) amino] pentanamide, (202) N-H
Droxy-2 (S) -benzyl-5-ethoxymethoxy
-4 (S)-[N- (4-nitrophenylcarbonyl)
Amino] pentanamide, (203) N-hydroxy-2
(S) -benzyl-5-ethoxymethoxy-4 (S)-
[N- (2,2,3,3-tetramethylcyclopropyl
Carbonyl) amino] pentanamide, (204) N-hi
Droxy-2 (S)-(3-methoxybenzyl) -5
Ethoxymethoxy-4 (S)-[N- (4-methylphen
Nylcarbonyl) amino] pentanamide, (205) N
-Hydroxy-2 (S) -benzyl-5-ethoxymethoate
Xy-4 (S)-[N- (1-cyclohexenylcarbo
Nyl) amino] pentanamide, (206) N-hydroxy
C-2 (S) -benzyl-5-ethoxymethoxy-4
(S)-[N [(1-cyclohexen-4-yl) cal
Bonyl] amino] pentanamide, (207) N-hydro
Xy-2 (S) -benzyl-5-ethoxymethoxy-4
(S)-[N- (4-dimethylaminophenylcarbonyl
Ru) amino] pentanamide, (208) N-hydroxy
-2 (S) -benzyl-5-ethoxymethoxy-4
(S)-[N- (4-carbamoylphenylcarbonyl)
Ru) amino] pentanamide, (209) N-hydroxy
-2 (S) -benzyl-5-ethoxymethoxy-4
(S)-[N- (4-methoxycarbonylphenylcar
Bonyl) amino] pentanamide, (210) N-hydro
Xy-2 (S) -benzyl-5-ethoxymethoxy-4
(S)-[N- (cyclopentylcarbonyl) amino]
Pentanamide, (211) N-hydroxy-2 (S)-
(Naphthalen-2-yl) -5-ethoxymethoxy-4
(S)-[N- (trans-4-methylcyclohexyl
Carbonyl) amino] pentanamide, (212) N-hi
Droxy-2 (S) -benzyl-5-ethoxymethoxy
-4 (S)-[N- (4-trifluoromethylphenyl
Carbonyl) amino] pentanamide, (213) N-hi
Droxy-2 (S) -benzyl-5-ethoxymethoxy
-4 (S)-[N- (4-iodophenylcarbonyl)
Amino] pentanamide, (214) N-hydroxy-2
(S) -benzyl-5-ethoxymethoxy-4 (S)-
[N- [4- (2-iodoethynyl) phenylcarboni]
[Amino] pentanamide, (215) N-hydroxy
-2 (S) -benzyl-5-ethoxymethoxy-4
(S)-[N- (cycloheptylcarbonyl) amino]
Pentanamide, (216) N-hydroxy-2 (S)-
Benzyl-5-ethoxymethoxy-4 (S)-[N-
(2-thienylcarbonyl) amino] pentanamide,
(217) N-hydroxy-2 (R)-(3,4,4-to
Limethyl-2,5-dioxoimidazolidin-1-i
M) methyl-5-ethoxymethoxy-4 (S)-[N-
(4-Methylphenylcarbonyl) amino] pentana
Mido, (218) N-hydroxy-2 (S) -benzyl-
5-ethoxymethoxy-4 (S)-[N-[(2-bromo
Mo-5-thienyl) carbonyl] amino] pentanami
, (219) N-hydroxy-2 (S) -benzyl-5
-Ethoxymethoxy-4 (S)-[N- (4-bromo
Enylcarbonyl) amino] pentanamide, (220)
N-hydroxy-2 (S) -benzyl-5-ethoxyme
Toxic-4 (S)-[N- (4-hydroxymethylphen
Nylcarbonyl) amino] pentanamide, (221) N
-Hydroxy-2 (S)-(benzothiophen-3-i
) -5-ethoxymethoxy-4 (S)-[N- (
4-Methylcyclohexylcarbonyl) amino]
Pentanamide, (222) N-hydroxy-2 (S)-
Benzyl-5-ethoxymethoxy-4 (S)-[N-
(4-cyanophenylcarbonyl) amino] pentana
Mido, (223) N-hydroxy-2 (S) -benzyl-
5-ethoxymethoxy-4 (S)-[N-[(1-ace
Tylpiperidin-4-yl) carbonyl] amino] pen
Tanamide, (224) N-hydroxy-2 (S) -ben
Zyl-5-ethoxymethoxy-4 (S)-[N-[(1
-Methylpiperidin-4-yl) carbonyl] amino]
Pentanamide, (225) N-hydroxy-2 (S)-
Benzyl-5-ethoxymethoxy-4 (S)-[N-
(4-Formylphenylcarbonyl) amino] pentane
Amide, (226) N-hydroxy-2 (S)-(3-meth
Toxylbenzyl) -5-ethoxymethoxy-4 (S)-
[N- (4-nitrophenylcarbonyl) amino] pen
Tanamide, (227) N-hydroxy-2 (S)-(3
-Methoxybenzyl) -5-ethoxymethoxy-4
(S)-[N- (4-chlorophenylcarbonyl) amido
No] pentanamide, (228) N-hydroxy-2
(S)-(4-methoxybenzyl) -5-ethoxymeth
Xy-4 (S)-[N- (4-methylphenylcarboni
Ru) amino] pentanamide, (229) N-hydroxy
-2 (S)-(2-methoxybenzyl) -5-ethoxy
Methoxy-4 (S)-[N- (4-methylphenylcarb
Bonyl) amino] pentanamide, (230) N-hydro
Xy-2 (S)-(naphthalen-1-yl) methyl-5
-Ethoxymethoxy-4 (S)-[N- (4-methylf
Enylcarbonyl) amino] pentanamide, (231)
N-hydroxy-2 (S)-(3-methoxybenzyl)
-5-ethoxymethoxy-4 (S)-[N- (trans
-4-methylcyclohexylcarbonyl) amino] pen
Tanamide, (232) N-hydroxy-2 (S) -ben
Jil-5-ethoxymethoxy-4 (S)-[N- (4-
Methoxycyclohexylcarbonyl) amino] pentane
Amide, (233) N-hydroxy-2 (S)-(benzo
Thiophen-3-yl) methyl-5-ethoxymethoxy
-4 (S)-[N- (4-bromophenylcarbonyl)
Amino] pentanamide, (234) N-hydroxy-2
(S)-(benzothiophen-3-yl) methyl-5
Ethoxymethoxy-4 (S)-[N- (4-chlorophen
Nylcarbonyl) amino] pentanamide, (235) N
-Hydroxy-2 (S) -benzyl-5-ethoxymethoate
Xy-4 (S)-[N-[(2-chloropyridine-5-
Yl) carbonyl] amino] pentanamide, (236)
N-hydroxy-2 (S)-(3,5-dimethoxyben
Zyl) -5-ethoxymethoxy-4 (S)-[N- (4
-Methylphenylcarbonyl) amino] pentanami
(237) N-hydroxy-2 (S) -benzyl-5
-Ethoxymethoxy-4 (S)-[N- (4-methyl
Clohexylcarbonyl) amino] pentanamide, (2
38) N-Hydroxy-2 (S)-(3-methoxybenz
Zyl) -5-ethoxymethoxy-4 (S)-[N- (4
-Cyanophenylcarbonyl) amino] pentanami
, (239) N-hydroxy-2 (R)-(3,4,4
-Trimethyl-2,5-dioxoimidazolidin-1-
Yl) methyl-5-ethoxymethoxy-4 (S)-[N
-(Trans-4-methylcyclohexylcarbonyl)
Amino] pentanamide, (240) N-hydroxy-2
(R)-(benzofuran-2-yl) methyl-5-ethoxy
Xymethoxy-4 (S)-[N- (trans-4-methyl
Rucyclohexylcarbonyl) amino] pentanami
, (241) N-hydroxy-2 (S)-(benzothio
Phen-3-yl) methyl-5-ethoxymethoxy-4
(S)-[N- (4-nitrophenylcarbonyl) amido
No] pentanamide, (242) N-hydroxy-2
(S) -benzyl-5-ethoxymethoxy-4 (S)-
[N- (4-cyanophenylcarbonyl) amino] pen
Tanamide, (243) N-hydroxy-2 (S) -ben
Jil-5-ethoxymethoxy-4 (S)-[N- (4-
Methylidenecyclohexylcarbonyl) amino] penta
Amide, (244) N-hydroxy-2 (S) -benzyl
Ru-5-ethoxymethoxy-4 (S)-[N-[(1-
Formylpiperidin-4-yl) carbonyl] amino]
Pentanamide, (245) N-hydroxy-2 (S)-
Benzyl-5-ethoxymethoxy-4 (S)-[N-
[(1-Methyl-1-cyclohexen-4-yl) cal
Bonyl] amino] pentanamide, (246) N-hydro
Xy-2 (S) -benzyl-5-ethoxymethoxy-4
(S)-[N-[(4-methyl-1-cyclohexene
Ru) carbonyl] amino] pentanamide, (247) N
-Hydroxy-2 (S) -benzyl-5-ethoxymethoate
Xy-4 (S)-[N- (4-fluorophenylcarbo
Nyl) amino] pentanamide, (248) N-hydroxy
C-2 (S) -benzyl-5-ethoxymethoxy-4
(S)-[N- (4-chlorophenylcarbonyl) amido
No] pentanamide, (249) N-hydroxy-2
(S) -benzyl-5-ethoxymethoxy-4 (S)-
[N- (4-hydroxycyclohexylcarbonyl) a
Mino] pentanamide, (250) N-hydroxy-2
(S)-(benzofuran-3-yl) methyl-5-eth
Xymethoxy-4 (S)-[N- (trans-4-methyl
Rucyclohexylcarbonyl) amino] pentanami
, (251) N-hydroxy-2 (S)-(3-methoxy)
Cibenzyl) -5-ethoxymethoxy-4 (S)-[N
-(4-trifluoromethylphenylcarbonyl) amido
No] pentanamide, (252) N-hydroxy-2
(S)-(1-methylindol-3-yl) methyl-
5- (2-methoxyethoxy) methoxy-4 (S)-
[N- (trans-4-methylcyclohexylcarbonyl)
Ru) amino] pentanamide, (253) N-hydroxy
-2 (S) -benzyl-5-ethoxymethoxy-4
(S)-[N-[(1,3-dithian-2-yl) cal
Bonyl] amino] pentanamide, (254) N-hydro
Xy-2 (S)-(3-methoxybenzyl) -5-etho
Xymethoxy-4 (S)-[N- (4-bromophenyl
Carbonyl) amino] pentanamide, (255) N-hi
Droxy-2 (S)-(3-methoxybenzyl) -5
Ethoxymethoxy-4 (S)-[N-[(2-bromothio
Offen-5-yl) carbonyl] amino] pentana
Mido, (256) N-hydroxy-2 (S)-(2-meth
(Xybenzyl) -5-ethoxymethoxy-4 (S)-
[N- (trans-4-methylcyclohexylcarbonyl)
Ru) amino] pentanamide, (257) N-hydroxy
-2 (S) -benzyl-5-ethoxymethoxy-4
(S)-[N-[(2-methylpyridin-5-yl) ca
Rubonyl] amino] pentanamide, (258) N-hydrido
Roxy-2 (S)-(benzofuran-3-yl) methyl
-5-ethoxymethoxy-4 (S)-[N- (4-nitro
Lphenylcarbonyl) amino] pentanamide, (25
9) N-hydroxy-2 (S) -benzyl-5-ethoxy
Cymethoxy-4 (S)-[N- (trans-4-hydro
Xycyclohexylcarbonyl) amino] pentanami
, (260) N-hydroxy-2 (S)-(3-chloro
(Benzyl) -5-ethoxymethoxy-4 (S)-[N-
(4-Methylphenylcarbonyl) amino] pentana
Mido, (261) N-hydroxy-2 (S) -benzyl-
5-ethoxymethoxy-4 (S)-[N-[(2-hydrido
Roxypyridin-5-yl) carbonyl] amino] pen
Tanamide, (262) N-hydroxy-2 (R)-
(3,4,4-trimethyl-2,5-dioxoimidazo
Lysin-1-yl) methyl-5-ethoxymethoxy-4
(S)-[N- (4-bromophenylcarbonyl) amido
No] pentanamide, (263) N-hydroxy-2
(S)-(3-methoxybenzyl) -5-ethoxymeth
Xy-4 (S)-[N- (4-dimethoxymethylphenyi)
Lecarbonyl) amino] pentanamide, (264) N-
Hydroxy-2 (S)-(3-trifluoromethyloxy
Cibenzyl) -5-ethoxymethoxy-4 (S)-[N
-(4-Chlorophenylcarbonyl) amino] pentane
Amide, (265) N-hydroxy-2 (S)-(3-meth
Toxylbenzyl) -5-ethoxymethoxy-4 (S)-
[N- [2-nitrothiophen-5-yl) carboni
[Amino] pentanamide, (266) N-hydroxy
-2 (R)-(benzotriazol-1-yl) methyl
-5-ethoxymethoxy-4 (S)-[N- (4-nitro
Lphenylcarbonyl) amino] pentanamide, (26
7) N-hydroxy-2 (R)-(3,4,4-trime
Tyl-2,5-dioxoimidazolidin-1-yl) me
Tyl-5-ethoxymethoxy-4 (S)-[N- (4-
Nitrophenylcarbonyl) amino] pentanamide,
(268) N-hydroxy-2 (R)-(3,4,4-to
Limethyl-2,5-dioxoimidazolidin-1-i
M) methyl-5-ethoxymethoxy-4 (S)-[N-
(4-Chlorophenylcarbonyl) amino] pentana
Mido, (269) N-hydroxy-2 (S)-(3-fe
Nylpropyl) -5-methoxymethoxy-4 (S)-
[N- (4-phenoxyphenylcarbonyl) amino]
Pentanamide, (270) N-hydroxy-2 (S)-
(3-phenylpropyl) -5-methoxymethoxy-4
(S)-[N- [4- [2E- (4-chlorophenyl)
Ethenyl] phenylcarbonyl] amino] pentanami
, (271) N-hydroxy-2 (S)-(3-phenyl
Propyl) -5-methoxymethoxy-4 (S)-[N
-[4- (4-phenyl-1,2,5,6-tetrahydrid
L-pyridin-1-yl) phenylcarbonyl] amino]
Pentanamide, (272) N-hydroxy-2 (S)-
(3-Phenyl-2-propenyl) -5-ethoxymeth
Xy-4 (S)-[N- (trans-4-methylcyclo
Hexylcarbonyl) amino] pentanamide, (273)
N-hydroxy-2 (S)-(3-phenylpropyl
) -5-ethoxymethoxy-4 (S)-[N- (
4-Methylcyclohexylcarbonyl) amino]
Pentanamide, (274) N-hydroxy-2 (S)-
(2-phenylethyl) -5- (2-methoxyethoxy)
B) methoxy-4 (S)-[N- (trans-4-methyl
Rucyclohexylcarbonyl) amino] pentanami
, (275) N-hydroxy-2 (S)-(4-phenyl
Rubutyl) -5- (2-methoxyethoxy) methoxy-
4 (S)-[N- (trans-4-methylcyclohexyl
Lecarbonyl) amino] pentanamide, (276) N-
Hydroxy-2 (S)-(3-phenylpropyl) -5
-Ethoxymethoxy-4 (S)-[N- (4-bromo
Enylcarbonyl) amino] pentanamide, (277)
N-hydroxy-2 (S)-(3-phenylpropyl)
-5-ethoxymethoxy-4 (S)-[N- (4-nitro
Lphenylcarbonyl) amino] pentanamide, (27
8) N-hydroxy-2 (R)-(2-phenoxyethyl
) -5-ethoxymethoxy-4 (S)-[N- (4-
Nitrophenylcarbonyl) amino] pentanamide,
(279) N-hydroxy-2 (R)-(2-pyridyl)
Methyl-5-methoxymethoxy-4 (S)-[N- (4
-Phenoxyphenylcarbonyl) amino] pentana
Mido, (280) N-hydroxy-2 (R)-(2-pyri
(Zyl) methyl-5-methoxymethoxy-4 (S)-[N
-[4- (benzofuran-2-yl) phenylcarboni
[Amino] pentanamide, (281) N-hydroxy
-2 (S)-(3-pyridyl) methyl-5-methoxymeth
Toxic-4 (S)-[N- (4-phenoxyphenylca
Rubonyl) amino] pentanamide, (282) N-hydrido
Roxy-2 (S)-(3-pyridyl) methyl-5-methoate
Xymethoxy-4 (S)-[N- [4- [2- (4-me
Tylphenyl) ethynyl] phenylcarbonyl] ami
No] pentanamide, (283) N-hydroxy-2
(S)-(3-pyridyl) methyl-5-methoxymethoxy
C-4 (S)-[N- [4- (1-heptynyl) phenyl]
[Carbonyl] amino] pentanamide, (284) N-
Hydroxy-2 (S)-(3-pyridyl) methyl-5
Methoxymethoxy-4 (S)-[N- [4- [2E-
(4-Chlorophenyl) ethenyl] phenylcarboni
[Amino] pentanamide, (285) N-hydroxy
-2 (S)-(3-pyridyl) methyl-5-methoxymeth
Toxic-4 (S)-[N- (trans-4-methylcyclyl)
Rohexylcarbonyl) amino] pentanamide, (28
6) N-hydroxy-2 (S)-(4-pyridyl) methyl
Ru-5-methoxymethoxy-4 (S)-[N- (4-f
Enoxyphenylcarbonyl) amino] pentanami
, (287) N-hydroxy-2 (R)-(2-pyridy
L) Methyl-5- (2-methoxyethoxy) methoxy-
4 (S)-[N- (4-phenoxyphenylcarboni
Ru) amino] pentanamide, (288) N-hydroxy
-2 (S)-(3-pyridyl) methyl-5-ethoxyme
Toxic-4 (S)-[N- (2-methylphenylcarbo
Nyl) amino] pentanamide, (289) N-hydroxy
C-2 (S)-(3-pyridyl) methyl-5-ethoxy
Methoxy-4 (S)-[N- (3-methylphenylcarb
Bonyl) amino] pentanamide, (290) N-hydro
Xy-2 (S)-(3-pyridyl) methyl-5-ethoxy
Cymethoxy-4 (S)-[N- (4-methylphenylca
Rubonyl) amino] pentanamide, (291) N-hydrido
Roxy-2 (S)-(3-pyridyl) methyl-5-eth
Xymethoxy-4 (S)-[N- (4-methoxyphenyl
Carbonyl) amino] pentanamide, (292) N-
Hydroxy-2 (S)-(3-pyridyl) methyl-5
Ethoxymethoxy-4 (S)-(N-cyclohexylca
Rubonylamino) pentanamide, (293) N-hydro
Xy-2 (S)-(3-pyridyl) methyl-5-ethoxy
Cymethoxy-4 (S)-[N- (4-nitrophenylca
Rubonyl) amino] pentanamide, (294) N-hydrido
Roxy-2 (S)-(3-pyridyl) methyl-5-eth
Xymethoxy-4 (S)-[N- (4-bromophenyl
Carbonyl) amino] pentanamide, (295) N-hi
Droxy-2 (S)-(3-quinolyl) methyl-5-e
Toximethoxy-4 (S)-[N- (trans-4-meth
Tylcyclohexylcarbonyl) amino] pentanami
, (296) N-hydroxy-2 (S) -phenylthio
-5-methoxymethoxy-4 (S)-[N- (4-fe
Nonoxyphenylcarbonyl) amino] pentanamide,
(297) N-hydroxy-2 (S) -phenylthio-5
-Ethoxymethoxy-4 (S)-[N- (trans-4
-Methylcyclohexylcarbonyl) amino] pentane
Amide, (298) N-hydroxy-2 (S) -methylthio
O-5-ethoxymethoxy-4 (S)-[N- (tran
S-4-methylcyclohexylcarbonyl) amino] pe
Tantanamide, (299) N-hydroxy-2 (S)-
(4-pyridyl) thio-5-ethoxymethoxy-4
(S)-[N- (trans-4-methylcyclohexyl
Carbonyl) amino] pentanamide, (300) N-H
Droxy-2 (S) -hydroxy-5-methoxymethoxy
C-4 (S)-[N- (4-phenoxyphenylcarbo
Nyl) amino] pentanamide, (301) N-hydroxy
C-2 (R) -hydroxymethyl-5-ethoxymethoxy
C-4 (S)-[N- (4-chlorophenylcarboni
Ru) amino] pentanamide, (302) N-hydroxy
-2 (R) -methoxymethyl-5-ethoxymethoxy-
4 (S)-[N- (4-nitrophenylcarbonyl) a
Mino] pentanamide, (303) N-hydroxy-2
(R) -benzyloxymethyl-5-ethoxymethoxy
-4 (S)-[N- (4-nitrophenylcarbonyl)
Amino] pentanamide, (304) N-hydroxy-2
(R)-(2-methoxyethoxy) methyl-5-ethoxy
Cymethoxy-4 (S)-[N- (4-nitrophenylca
Rubonyl) amino] pentanamide, (305) N-hydrido
Roxy-2 (R) -methoxymethyl-5- (2-methoxy
Siethoxy) methoxy-4 (S)-[N- (4-cyano
Phenylcarbonyl) amino] pentanamide, (306)
N-hydroxy-2 (R) -methoxymethyl-5-e
Toximethoxy-4 (S)-[N- (trans-4-meth
Tylcyclohexylcarbonyl) amino] pentanami
, (307) N-hydroxy-2 (R) -methoxymethyl
Ru-5-ethoxymethoxy-4 (S)-[N- (4-butyl
Lomophenylcarbonyl) amino] pentanamide, (3
08) N-hydroxy-2 (R) -methoxymethyl-5
-Ethoxymethoxy-4 (S)-[N- (4-chlorofu
Enylcarbonyl) amino] pentanamide, (309)
N-hydroxy-2 (R) -benzyloxymethyl-5
-(2-methoxyethoxy) methoxy-4 (S)-[N
-(4-cyanophenylcarbonyl) amino] pentane
Amide, (310) N-hydroxy-2 (R) -benzyl
Oxymethyl-5-ethoxymethoxy-4 (S)-[N
-(4-Chlorophenylcarbonyl) amino] pentane
Amide, (311) N-hydroxy-2 (R) -benzyl
Oxymethyl-5-ethoxymethoxy-4 (S)-[N
-(4-Bromophenylcarbonyl) amino] pentane
Amide, (312) N-hydroxy-2 (R)-[2-
(3-methoxyphenoxy) ethyl] -5-ethoxyme
Toxic-4 (S)-[N- (4-nitrophenylcarbo
Nyl) amino] pentanamide, (313) N-hydroxy
C-2 (R) -methoxymethyl-5-ethoxymethoxy
-4 (S)-[N-[(2-nitrothiophen-5-i
Le) carbonyl] amino] pentanamide, (314) N
-Hydroxy-2 (R) -methoxymethyl-5-ethoxy
Cymethoxy-4 (S)-[N-[(2-bromothiophene
N-5-yl) carbonyl] amino] pentanamide,
(315) N-hydroxy-2 (R)-(2-methoxy
Toxy) methyl-5-ethoxymethoxy-4 (S)-
[N- (4-bromophenylcarbonyl) amino] pen
Tanamide, (316) N-hydroxy-2 (R)-(2
-Methoxyethoxy) methyl-5- (2-methoxyethoxy
Xy) methoxy-4 (S)-[N- (4-cyanophenyi)
Carbonyl) amino] pentanamide, (317) N-
Hydroxy-2 (R)-(2-methoxyethoxy) methyl
Ru-5-ethoxymethoxy-4 (S)-[N- (4-
Lorophenylcarbonyl) amino] pentanamide, (3
18) N-hydroxy-2 (R) -benzyloxymethyl
5-ethoxymethoxy-4 (S)-[N- (tran
S-4-methylcyclohexylcarbonyl) amino] pe
Tantanamide, (319) N-hydroxy-2 (R)-
(3-thienyl) methoxymethyl-5-ethoxymethoxy
C-4 (S)-[N- (4-nitrophenylcarboni
Ru) amino] pentanamide, (320) N-hydroxy
-2 (R)-(2-pyridinyl) methyl-5-hydroxy
C-4 (S)-[N- (4-phenoxyphenylcarbo
Nyl) amino] pentanamide, (321) N-hydroxy
C-2 (S) -methyl-5-hydroxy-4 (S)-
[N- (4-phenoxyphenylcarbonyl) amino]
Pentanamide, (322) N-hydroxy-2 (S)-
Methyl-5-hydroxy-4 (S)-[N- (4-bro
Mophenylcarbonyl) amino] pentanamide, (32
3) N-hydroxy-2 (S)-(3-methoxybenzyl)
) -5-hydroxy-4 (S)-[N- (4-bromo
Phenylcarbonyl) amino] pentanamide, (324)
N-hydroxy-2 (S)-(3-methoxybenzyl
Ru) -5-hydroxy-4 (S)-[N- (4-nitro
Phenylcarbonyl) amino] pentanamide, (325)
N-hydroxy-2 (S)-(3-methoxybenzyl
Ru) -5-hydroxy-4 (S)-[N- (4-chloro
Phenylcarbonyl) amino] pentanamide, (326)
N-hydroxy-2 (S)-(3-methoxybenzyl
) -5-hydroxy-4 (S)-[N-[(2-bromo
Mothiophen-5-yl) carbonyl] amino] penta
Amide, (327) N-hydroxy-2 (S)-(3-
(Methoxybenzyl) -5-hydroxy-4 (S)-[N
-[(2-nitrothiophen-5-yl) carbonyl]
Amino] pentanamide, (328) N-hydroxy-2
(S)-(3-methoxybenzyl) -5-hydroxy-
4 (S)-[N- (4-cyanophenylcarbonyl) a
Mino] pentanamide, (329) N-hydroxy-2
(R) -benzyloxymethyl-5-hydroxy-4
(S)-[N- (4-nitrophenylcarbonyl) amido
No] pentanamide, (330) N-hydroxy-5-meth
Toximethoxy-4 (S)-[N-methyl-N- [4-
(4-chlorophenyl) phenylcarbonyl] amino]
Pentanamide, (331) N-hydroxy-2 (S)-
(3-pyridyl) methyl-5-methoxymethoxy-4
(S)-[N-methyl-N- [4- (4-chlorophenyl
Ru) phenylcarbonyl] amino] pentanamide, (3
32) N-hydroxy-2 (S) -methyl-5-ethoxy
Cymethoxy-4 (S)-[N-methyl-N- (4-bro
Mophenylcarbonyl) amino] pentanamide, (33
3) N-hydroxy-2 (S)-(3-methoxybenzyl)
) -5-ethoxymethoxy-4 (S)-[N-methyl
-N- (4-bromophenylcarbonyl) amino] pen
Tanamide, (334) N-hydroxy-2 (S) -methyl
Ru-5-ethoxymethoxy-4 (S)-[N-methyl-
N- (4-nitrophenylcarbonyl) amino] penta
Amide, (335) N-hydroxy-2 (S) -methyl
-5-benzyloxymethoxy-4 (S)-[N-methyl
Ru-N- (4-nitrophenylcarbonyl) amino] pe
Tantanamide, (336) N-hydroxy-2 (S)-
(3-methoxybenzyl) -5-hydroxy-4 (S)
-[N-methyl-N- (4-chlorophenylcarbonyl)
Ru) amino] pentanamide, (337) N-hydroxy
-2 (S)-(3-methoxybenzyl) -5-hydroxy
C-4 (S)-[N-methyl-N- (4-nitrophenyl
Carbonyl) amino] pentanamide, (338) N-
Hydroxy-2 (S)-(3-methoxybenzyl) -5
-Hydroxy-4 (S)-[N-methyl-N- (4-butyl
Lomophenylcarbonyl) amino] pentanamide, (3
39) N-hydroxy-2 (S) -methyl-5-hydro
Xy-4 (S)-[N-methyl-N- (4-nitrophen
Nylcarbonyl) amino] pentanamide, (340) N
-Hydroxy-2 (S) -benzyl-5-hydroxy-
4 (S)-[N-methyl-N- (4-nitrophenylca)
Rubonyl) amino] pentanamide, (341) N-hydrido
Roxy-2 (S) -methyl-5-hydroxy-4 (S)
-[N-methyl-N- (4-bromophenylcarbonyl)
Ru) amino] pentanamide, (342) N-hydroxy
-2 (S) -benzyl-5-hydroxy-4 (S)-
[N-methyl-N- (4-bromophenylcarbonyl)
Amino] pentanamide, (343) N-hydroxy-2
(S) -methyl-5-hydroxy-4 (S)-[N-meth
Tyl-N- (4-chlorophenylcarbonyl) amino]
Pentanamide, (344) N-hydroxy-2 (S)-
Benzyloxy-3 (S) -hydroxy-4- (N-
(4- (3-methoxy-1-propynyl) phenylcar
Bonyl) amino) butyramide, (345) N-hydroxy
-2-benzyloxy-4- (N- (4- (3-methoxy
Ci-1-propynyl) phenylcarbonyl) amino)-
2-butenamide, (346) cis-1- (N-hydroxy
Cyaminocarbonylmethyl) -2- (N- (4- (3-
Methoxy-1-propynyl) phenylcarbonyl) amido
G) cyclopentane, (347) trans-1- (N-
Droxyaminocarbonylmethyl) -2- (N- (4-
(3-methoxy-1-propynyl) phenylcarboni
Ru) amino) cyclopentane, (348) trans-1-
(N-hydroxyaminocarbonyl) -3- (N- (4
-(3-methoxy-1-propynyl) phenyl carbonyl
Ru) amino) cyclopentane, (349) cis-1- (N
-Hydroxyaminocarbonyl) -3- (N- (4-
(3-methoxy-1-propynyl) phenylcarboni
Ru) amino) cyclopentane, (350) trans-1-
(N-hydroxyaminocarbonyl) -2- (N- (4
-(3-methoxy-1-propynyl) phenyl carbonyl
Ru) aminomethyl) cyclopentane, (351) N-hydrido
Roxy-2 (R) -allyl-5-ethoxymethoxy-4
(S)-[N- (4-phenoxyphenylcarbonyl)
Amino] pentanamide, (352) N-hydroxy-2
(R) -benzyl-5-methoxymethoxy-4 (S)-
[N- [4- (benzofuran-2-yl) phenylcal
Bonyl] amino] pentanamide, (353) N-hydro
Xy-2 (R) -methyl-5-ethoxymethoxy-4
(S)-[N- (4-phenoxyphenylcarbonyl)
Amino] pentanamide, (354) N-hydroxy-2
(R) -methyl-5-ethoxymethoxy-4 (S)-
[N- [4- (4-cyanophenyl) phenylcarbonyl]
[Amino] pentanamide, (355) N-hydroxy
-2 (S) -benzyl-5-methoxymethoxy-4
(R)-[N- (4-phenoxyphenylcarbonyl)
Amino] pentanamide, (356) N-hydroxy-2
(S) -benzyl-5-methoxymethoxy-4 (R)-
[N- [4- (3-phenoxy-1-propynyl) fe
Nylcarbonyl] amino] pentanamide, (357) N
-Hydroxy-2 (S)-(3-aminobenzyl) -5
-Ethoxymethoxy-4 (S)-[N- (trans-4
-Methylcyclohexylcarbonyl) amino] pentane
Amide, (358) N-hydroxy-2 (S) -benzyl
-5-ethoxymethoxy-4 (S)-[N- (4-cal
Boxyphenylcarbonyl) amino] pentanamide,
(359) N-hydroxy-2 (S) -benzyl-5-e
Toximethoxy-4 (S)-[N- (4-aminopheni
Lecarbonyl) amino] pentanamide, (360) N-
Hydroxy-2 (S) -benzyl-5-ethoxymethoxy
C-4 (S)-[N- (4-piperidylcarbonyl) a
Mino] pentanamide, (361) N-hydroxy-2
(S)-(3-hydroxybenzyl) -5-ethoxyme
Toxic-4 (S)-[N- (4-methylphenylcarbo
Nyl) amino] pentanamide, (362) N-hydroxy
C-2-benzyl-4- [N- [4- (benzofuran-
2-yl) phenylcarbonyl] amino] butyramide,
(363) N-hydroxy-2- (3-phenylpropyl
) -4- [N- [4- (benzofuran-2-yl) phenyl
Enylcarbonyl] amino] butyramide, (364) N-
Hydroxy-2- (2-phenylethyl) -4- [N-
[4- (benzofuran-2-yl) phenylcarboni
[Amino] butyramide, (365) N-hydroxy-2
-Benzyl-4- [N- [4- [2E- (4-chlorof
Enyl) ethenyl] phenylcarbonyl] amino] buty
Lamide, (366) N-hydroxy-2-benzyl-4-
[N- (4-phenoxyphenylcarbonyl) amino]
Butyramide, (367) N-hydroxy-2- (naphthale
N-1-yl) methyl-4- [N- (4-phenoxyf
Enylcarbonyl) amino] butyramide, (368) N-
Hydroxy-2-isopropyl-4- [N- (4-fe
Noxyphenylcarbonyl) amino] butyramide, (36
9) N-hydroxy-2- (quinolin-4-yl) methyl
Ru-4- [N- (4-phenoxyphenylcarbonyl)
Amino] butyramide, (370) N-hydroxy-2-
(2-pyridyl) methyl-4- [N- (4-phenoxy
Phenylcarbonyl) amino] butyramide, (371) N
-Hydroxy-2- (3-pyridyl) methyl-4- [N
-(4-phenoxyphenylcarbonyl) amino] buty
Lamid, (372) N-hydroxy-2- (naphthalene-
2-yl) methyl-4- [N- (4-phenoxyphenyi
Carbonyl) amino] butyramide, (373) N-hydrido
Roxy-2- (4-pyridyl) methyl-4- [N- (4
-Phenoxyphenylcarbonyl) amino] butyrami
(374) N-hydroxy-2- (3-methoxybenz)
Zyl) -4- [N- (4-phenoxyphenylcarboni
Ru) amino] butyramide, (375) N-hydroxy-2
-Isobutyl-4- [N- (4-phenoxyphenylca)
Rubonyl) amino] butyramide, (376) N-hydroxy
C-5-methoxy-4 (S)-[N- [4- (4-chloro
Lphenyl) phenylcarbonyl] amino] pentana
Mido, (377) N-hydroxy-2 (S) -methyl-5
-Succinimide-4 (S)-[N- (4-chlorophen
Nylcarbonyl) amino] pentanamide, (378) N
-Hydroxy-2 (S) -methyl-5-succinimide
Oxy-4 (S)-[N-methyl-N- (4-nitrofuran
(Enylcarbonyl) amino] pentanamide, (379)
N-hydroxy-2 (S) -methyl-5-ethoxymeth
Xy-4 (S)-[N- (4-phenoxyphenylcar
Bonyl) amino] pentanamide, (380) N-hydro
Xy-2 (S) -allyl-5-ethoxymethoxy-4
(S)-[N- (4-phenoxyphenylcarbonyl)
Amino] pentanamide, (381) N-hydroxy-2
(S) -methyl-5-ethoxymethoxy-4 (S)-
[N- [4- (4-cyanophenyl) phenylcarbonyl]
[Amino] pentanamide or a non-toxic salt thereof
The compound according to claim 2, which is 11. The compound according to claim 1, wherein (1) 1-acetylthio-
5-ethoxymethoxy-4- [N- (4-phenoxyphenylcarbonyl) amino] pentane, (2) 5-ethoxymethoxy-4- [N- (4-phenoxyphenylcarbonyl) amino] pentanethiol, or their non- The compound according to claim 2, which is a toxic salt. 12. The compound represented by the formula (64) 2 (S)-(2-propynyl) -5-ethoxymethoxy-4 (S)-[N-
(4-Nitrophenylcarbonyl) amino] pentanoic acid, (67) 2 (S)-(2-propynyl) -5-ethoxymethoxy-4 (S)-[N- (4-bromophenylcarbonyl) amino] pentanoic acid , (68) 2 (S)-(2
-Propynyl) -5-ethoxymethoxy-4 (S)-
[N- (4-chlorophenylcarbonyl) amino] pentanoic acid, (79) 2 (S)-(2-propynyl) -5-
(2-methoxyethoxy) methoxy-4 (S)-[N-
The compound according to claim 3, which is (4-cyanophenylcarbonyl) amino] pentanoic acid or a non-toxic salt thereof. 13. The method according to claim 13, wherein the compound is (170) N-hydroxy-
2 (S)-(2-propynyl) -5-ethoxymethoxy-4 (S)-[N- (4-nitrophenylcarbonyl)
Amino] pentanamide, (172) N-hydroxy-2
(S)-(2-propynyl) -5-ethoxymethoxy-
4 (S)-[N- (4-bromophenylcarbonyl) amino] pentanamide, (173) N-hydroxy-2
(S)-(2-propynyl) -5-ethoxymethoxy-
4 (S)-[N- (4-chlorophenylcarbonyl) amino] pentanamide, (177) N-hydroxy-2
(S)-(2-propynyl) -5- (2-methoxyethoxy) methoxy-4 (S)-[N- (4-cyanophenylcarbonyl) amino] pentanamide or a non-toxic salt thereof. 3. The compound according to 3. (14) the compound is (26) N-hydroxy-5-
[N- [4- (benzofuran-2-yl) phenylcarbonyl] amino] pentanamide, (27) N-hydroxy-6- [N- [4- (benzofuran-2-yl) phenylcarbonyl] amino] hexanamide Or a non-toxic salt thereof. 15. A metalloproteinase inhibitor comprising the compound according to claim 1 as an active ingredient. 16. A rheumatism, osteoarthritis, pathological bone resorption, osteoporosis, periodontal disease, interstitial nephritis, arteriosclerosis, pulmonary emphysema, cirrhosis, cornea, containing the compound according to claim 1 or 14 as an active ingredient. Injury, disease of cancer cell metastasis invasion or proliferation, autoimmune disease (Crohn disease, Shugren disease, etc.),
A preventive and / or therapeutic agent for diseases caused by vascular migration or infiltration of leukocyte cells, angiogenesis, multiple sclerosis, aortic aneurysm, endometriosis and the like.