# US 8,785,462 B2 · 5-hydroxypyrimidine-4-carboxamide derivative

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- Number: US 8,785,462 B2
- Document ID: US8785462B2
- Status: Granted
- Kind: B2
- Application number: 13/503,340
- Filed: 2010-10-20
- Published: 2012-08-30
- Granted: 2014-07-22
- Earliest claimed: 2009-10-21
- Assignees: Daiichi Sankyo Company, Limited
- Applicants: Takeshi Kuribayashi; Hideki Kubota; Naoki Tanaka; Takeshi Fukuda; Takashi Tsuji; Riki Goto
- Inventors: Takeshi Kuribayashi; Hideki Kubota; Naoki Tanaka; Takeshi Fukuda; Takashi Tsuji; Riki Goto
- Web page: https://patentgrep.com/patent/US8785462B2

## CPC

- C07D 401/06: linked by a carbon chain containing only aliphatic carbon atoms
- A61P 7/00: Drugs for disorders of the blood or the extracellular fluid
- A61P 7/06: Antianaemics
- C07D 401/14: containing three or more hetero rings
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

The present invention provides a compound which enhances the production of erythropoietin. The present invention provides a compound represented by formula (1): [wherein, R1: formula (1A): [wherein, R4 and R5: H, halogen, or alkyl; R6: H, halogen, alkyl, or the like; R7: substitutable hydroxyalkyl, substitutable hydroxyhalo alkyl, substitutable alkoxyalkyl, or the like; substituent group α: oxo, hydroxy, amino, or the like; ring Q1: a monocyclic heterocyclic group; ring Q2: a monocyclic hydrocarbon ring group, or a monocyclic heterocyclic group; ring Q3: a monocyclic hydrocarbon ring group, or a monocyclic heterocyclic group; X: a single bond, methylene, ethylene, or the like]; R2: alkyl, or methylsulfanyl; and R3: H, or methyl], or the like.

## Claims

### Claim 1

A compound represented by formula (1):
wherein,
R1 represents a group represented by formula (1A):
wherein,
R4 and R5 each independently represents a hydrogen atom, a halogen atom or a C1-C6 alkyl group,
R6 represents a hydrogen atom, a halogen atom, a C1-C6 alkyl group, a carbamoyl group, a C1-C6 alkylcarbamoyl group, or a (C1-C6 alkyl)(C1-C6 alkyl)carbamoyl group,
R7 represents a hydroxy C1-C6 alkyl group which may have 1 or 2 substituents independently selected from substituent group α, a hydroxyhalo C1-C6 alkyl group which may have 1 or 2 substituents independently selected from substituent group α, a C1-C6 alkoxy C1-C6 alkyl group which may have 1 or 2 substituents independently selected from substituent group α, a (C1-C6 alkoxy)carbonyl group which may have 1 or 2 substituents independently selected from substituent group α, a C1-C6 alkoxy C1-C6 alkoxy C1-C6 alkyl group which may have 1 or 2 substituents independently selected from substituent group α, a hydroxy C1-C6 alkoxy group which may have 1 or 2 substituents independently selected from substituent group α, a C1-C6 alkylcarbamoyl group which may have 1 or 2 substituents independently selected from substituent group α, a (C1-C6 alkyl)(C1-C6 alkyl)carbamoyl group which may have 1 or 2 substituents independently selected from substituent group α, a C1-C6 alkoxycarbamoyl group which may have 1 or 2 substituents independently selected from substituent group α, a C1-C6 alkylcarbamoyl C1-C6 alkyl group which may have 1 or 2 substituents independently selected from substituent group α, a (C1-C6 alkyl)(C1-C6 alkyl)carbamoyl C1-C6 alkyl group which may have 1 or 2 substituents independently selected from substituent group α, a C2-C7 alkanoylamino group which may have 1 or 2 substituents independently selected from substituent group α, a C2-C7 alkanoylamino C1-C6 alkyl group which may have 1 or 2 substituents independently selected from substituent group α, or a C2-C7 alkanoyloxy C1-C6 alkyl group which may have 1 or 2 substituents independently selected from substituent group α,
substituent group α represents a group consisting of an oxo group, a hydroxy group, an amino group, a carboxy group, a carbamoyl group, a C1-C6 alkoxy group, a halo C1-C6 alkoxy group, a C2-C7 alkanoylamino group, a hydroxyimino group, and a C1-C6 alkoxyimino group,
ring Q1 represents a monocyclic heterocyclic group, wherein the heterocyclic group comprises a 5- to 7-membered aromatic heterocycle and non-aromatic heterocycle, and contains 1 or 2 atoms selected from the group consisting of a nitrogen atom, a sulfur atom and an oxygen atom,
ring Q2 represents a monocyclic hydrocarbon ring group, wherein the hydrocarbon ring group comprises a 5- to 7-membered aromatic hydrocarbon ring and a non-aromatic hydrocarbon ring, or a monocyclic heterocyclic group, wherein the heterocyclic group comprises a 5- to 7-membered aromatic heterocycle and non-aromatic heterocycle, and contains 1 or 2 atoms selected from the group consisting of a nitrogen atom, a sulfur atom and an oxygen atom,
ring Q3 represents a monocyclic hydrocarbon ring group, wherein the hydrocarbon ring group comprises a 5- to 7-membered aromatic hydrocarbon ring and a non-aromatic hydrocarbon ring, or a monocyclic heterocyclic group, wherein the heterocyclic group comprises a 5- to 7-membered aromatic heterocycle and non-aromatic heterocycle, and contains 1 or 2 atoms selected from the group consisting of a nitrogen atom, a sulfur atom and an oxygen atom, and
X represents a single bond, methylene, or ethylene,
R2 represents a C1-C3 alkyl group or a methylsulfanyl group, and
R3 represents a hydrogen atom or a methyl group, a pharmacologically acceptable ester thereof, or a pharmacologically acceptable salt thereof.

### Claim 2 (depends on 1)

The compound, pharmacologically acceptable ester thereof, or pharmacologically acceptable salt thereof according to claim 1, wherein R2 is a methyl group or a methylsulfanyl group.

### Claim 3 (depends on 1)

The compound, pharmacologically acceptable ester thereof, or pharmacologically acceptable salt thereof according to claim 1, wherein R2 is a methyl group.

### Claim 4 (depends on 1)

The compound, pharmacologically acceptable ester thereof, or pharmacologically acceptable salt thereof according to claim 1, wherein R3 is a hydrogen atom.

### Claim 5 (depends on 1)

The compound, pharmacologically acceptable ester thereof, or pharmacologically acceptable salt thereof according to claim 1, wherein R4 is a hydrogen atom.

### Claim 6 (depends on 1)

The compound, pharmacologically acceptable ester thereof, or pharmacologically acceptable salt thereof according to claim 1, wherein R5 is a hydrogen atom, a halogen atom or a methyl group.

### Claim 7 (depends on 1)

The compound, pharmacologically acceptable ester thereof, or pharmacologically acceptable salt thereof according to claim 1, wherein R5 is a hydrogen atom.

### Claim 8 (depends on 1)

The compound, pharmacologically acceptable ester thereof, or pharmacologically acceptable salt thereof according to claim 1, wherein R6 is a hydrogen atom, a halogen atom, or a methyl group.

### Claim 9 (depends on 1)

The compound, pharmacologically acceptable ester thereof, or pharmacologically acceptable salt thereof according to claim 1, wherein R6 is a hydrogen atom.

### Claim 10 (depends on 1)

The compound, pharmacologically acceptable ester thereof, or pharmacologically acceptable salt thereof according to claim 1, wherein R7 is a hydroxy C1-C6 alkyl group, a hydroxyhalo C1-C6 alkyl group, a C1-C6 alkoxy C1-C6 alkyl group, a hydroxy C1-C6 alkoxy C1-C6 alkyl group, a (C1-C6 alkoxy)carbonyl group, a C1-C6 alkoxy C1-C6 alkoxy C1-C6 alkyl group, a hydroxy C1-C6 alkoxy group, a C1-C6 alkylcarbamoyl group, a (C1-C6 alkyl)(C1-C6 alkyl)carbamoyl group, a hydroxy C1-C6 alkylcarbamoyl group, a C1-C6 alkoxycarbamoyl group, a C1-C6 alkylcarbamoyl C1-C6 alkyl group, a (C1-C6 alkyl)(C1-C6 alkyl)carbamoyl C1-C6 alkyl group, or a hydroxy C1-C6 alkylcarbamoyl C1-C6 alkyl group.

### Claim 11 (depends on 1)

The compound, pharmacologically acceptable ester thereof, or pharmacologically acceptable salt thereof according to claim 1, wherein R7 is a hydroxymethyl group, a 1-hydroxyethyl group, a 2-hydroxyethyl group, a 1,1-difluoro-2-hydroxyethyl group, a 2-hydroxypropyl group, a 3-hydroxypropyl group, a 1,1-difluoro-2-hydroxypropyl group, a 2-hydroxybutyl group, a 2-hydroxy-1,1-dimethylethyl group, a 1,1-difluoro-2-hydroxy-2-methylpropyl group, a methoxymethyl group, a 2-hydroxy-3-methoxypropyl group, a methoxycarbonyl group, an ethoxycarbonyl group, a methoxymethoxymethyl group, a 1-methoxymethoxyethyl group, a 2-hydroxyethoxy group, a methylcarbamoyl group, a dimethylcarbamoyl group, a methylcarbamoylmethyl group, a dimethylcarbamoylmethyl group, a hydroxyethylcarbamoyl group, or a hydroxyethylcarbamoylmethyl group.

### Claim 12 (depends on 1)

The compound, pharmacologically acceptable ester thereof, or pharmacologically acceptable salt thereof according to claim 1, wherein R7 is a hydroxymethyl group, a 1-hydroxyethyl group, a 2-hydroxyethyl group, a 2-hydroxypropyl group, a 3-hydroxypropyl group, a 2-hydroxybutyl group, a 2-hydroxy-1,1-dimethylethyl group, a methoxymethyl group, a 2-hydroxy-3-methoxypropyl group, an ethoxycarbonyl group, a 1-methoxymethoxyethyl group, a 2-hydroxyethoxy group, a methylcarbamoyl group, a dimethylcarbamoyl group, or a dimethylcarbamoylmethyl group.

### Claim 13 (depends on 1)

The compound, pharmacologically acceptable ester thereof, or pharmacologically acceptable salt thereof according to claim 1, wherein the ring Q1 is a monocyclic heterocyclic group, wherein the heterocyclic group comprises a 6-membered aromatic heterocycle and non-aromatic heterocycle, and contains 1 or 2 nitrogen atoms.

### Claim 14 (depends on 1)

The compound, pharmacologically acceptable ester thereof, or pharmacologically acceptable salt thereof according to claim 1, wherein the ring Q1 is a piperidyl group.

### Claim 15 (depends on 1)

The compound, pharmacologically acceptable ester thereof, or pharmacologically acceptable salt thereof according to claim 1, wherein the ring Q2 is a monocyclic hydrocarbon ring group (wherein the hydrocarbon ring group comprises a 6-membered aromatic hydrocarbon ring and a non-aromatic hydrocarbon ring), or a monocyclic heterocyclic group, wherein the heterocyclic group comprises a 6-membered aromatic heterocycle and non-aromatic heterocycle, and contains 1 or 2 nitrogen atoms.

### Claim 16 (depends on 1)

The compound, pharmacologically acceptable ester thereof, or pharmacologically acceptable salt thereof according to claim 1, wherein the ring Q2 is a phenyl group or a pyridyl group.

### Claim 17 (depends on 1)

The compound, pharmacologically acceptable ester thereof, or pharmacologically acceptable salt thereof according to claim 1, wherein the ring Q3 is a monocyclic hydrocarbon ring group, wherein the hydrocarbon ring group comprises a 6-membered aromatic hydrocarbon ring and a non-aromatic hydrocarbon ring, or a monocyclic heterocyclic group, wherein the heterocyclic group comprises a 6-membered aromatic heterocycle and non-aromatic heterocycle, and contains 1 or 2 nitrogen atoms.

### Claim 18 (depends on 1)

The compound, pharmacologically acceptable ester thereof, or pharmacologically acceptable salt thereof according to claim 1, wherein the ring Q3 is a phenyl group or a pyridyl group.

### Claim 19 (depends on 1)

The compound, pharmacologically acceptable ester thereof, or pharmacologically acceptable salt thereof according to claim 1, wherein X is a single bond or methylene.

### Claim 20 (depends on 1)

The compound, pharmacologically acceptable ester thereof, or pharmacologically acceptable salt thereof according to claim 1, wherein:
R1 is a group represented by formula (1B)
wherein,
R5 represents a hydrogen atom, a halogen atom or a C1-C6 alkyl group,
R6 represents a hydrogen atom, a halogen atom, a C1-C6 alkyl group, a carbamoyl group, a C1-C6 alkylcarbamoyl group, or a (C1-C6 alkyl)(C1-C6 alkyl)carbamoyl group,
R7 represents a hydroxymethyl group, a 1-hydroxyethyl group, a 2-hydroxyethyl group, a 1,1-difluoro-2-hydroxyethyl group, a 2-hydroxypropyl group, a 3-hydroxypropyl group, a 1,1-difluoro-2-hydroxypropyl group, a 2-hydroxybutyl group, a 2-hydroxy-1,1-dimethylethyl group, a 1,1-difluoro-2-hydroxy-2-methylpropyl group, a methoxymethyl group, a 2-hydroxy-3-methoxypropyl group, a methoxycarbonyl group, an ethoxycarbonyl group, a methoxymethoxymethyl group, a 1-methoxymethoxyethyl group, a 2-hydroxyethoxy group, a methylcarbamoyl group, a dimethylcarbamoyl group, a methylcarbamoylmethyl group, a dimethylcarbamoylmethyl group, a hydroxyethylcarbamoyl group, or a hydroxyethylcarbamoylmethyl group,
V, W and Y, each independently, represent a carbon atom having 1 hydrogen atom or a nitrogen atom, and
X represents a single bond or methylene.

### Claim 21 (depends on 1)

The compound, pharmacologically acceptable ester thereof, or pharmacologically acceptable salt thereof according to claim 1, wherein:
R1 represents a group represented by formula (1B-1), (1B-2), (1B-3), (1B-4), (1B-5), (1B-6), (1B-7), or (1B-8)
wherein,
R7 represents a hydroxymethyl group, a 1-hydroxyethyl group, a 2-hydroxyethyl group, a 1,1-difluoro-2-hydroxyethyl group, a 2-hydroxypropyl group, a 3-hydroxypropyl group, a 1,1-difluoro-2-hydroxypropyl group, a 2-hydroxybutyl group, a 2-hydroxy-1,1-dimethylethyl group, a 1,1-difluoro-2-hydroxy-2-methylpropyl group, a methoxymethyl group, a 2-hydroxy-3-methoxypropyl group, a methoxycarbonyl group, an ethoxycarbonyl group, a methoxymethoxymethyl group, a 1-methoxymethoxyethyl group, a 2-hydroxyethoxy group, a methylcarbamoyl group, a dimethylcarbamoyl group, a methylcarbamoylmethyl group, a dimethylcarbamoylmethyl group, a hydroxyethylcarbamoyl group, or a hydroxyethylcarbamoylmethyl group.

### Claim 22 (depends on 1)

The compound, pharmacologically acceptable ester thereof, or pharmacologically acceptable salt thereof according to claim 1, wherein:
R1 represents a group represented by formula (1B-1), (1B-2), (1B-3), (1B-5), or (1B-6)
wherein,
R7 represents a hydroxymethyl group, a 1-hydroxyethyl group, a 2-hydroxyethyl group, a 1,1-difluoro-2-hydroxyethyl group, a 2-hydroxypropyl group, a 3-hydroxypropyl group, a 1,1-difluoro-2-hydroxypropyl group, a 2-hydroxybutyl group, a 2-hydroxy-1,1-dimethylethyl group, a 1,1-difluoro-2-hydroxy-2-methylpropyl group, a methoxymethyl group, a 2-hydroxy-3-methoxypropyl group, a methoxycarbonyl group, an ethoxycarbonyl group, a methoxymethoxymethyl group, a 1-methoxymethoxyethyl group, a 2-hydroxyethoxy group, a methylcarbamoyl group, a dimethylcarbamoyl group, a methylcarbamoylmethyl group, a dimethylcarbamoylmethyl group, a hydroxyethylcarbamoyl group, or a hydroxyethylcarbamoylmethyl group.

### Claim 23 (depends on 20)

The compound, pharmacologically acceptable ester thereof, or pharmacologically acceptable salt thereof according to claim 20, wherein R7 represents a hydroxymethyl group, a 1-hydroxyethyl group, a 2-hydroxyethyl group, a 2-hydroxypropyl group, a 3-hydroxypropyl group, a 2-hydroxybutyl group, a 2-hydroxy-1,1-dimethylethyl group, a methoxymethyl group, a 2-hydroxy-3-methoxypropyl group, an ethoxycarbonyl group, a 1-methoxymethoxyethyl group, a 2-hydroxyethoxy group, a methylcarbamoyl group, a dimethylcarbamoyl group, or a dimethylcarbamoylmethyl group.

### Claim 24 (depends on 20)

The compound, pharmacologically acceptable ester thereof, or pharmacologically acceptable salt thereof according to claim 20, wherein, in the case where R7 represents a group having a hydroxy group (a hydroxy C1-C6 alkyl group, a hydroxyhalo C1-C6 alkyl group, a hydroxy C1-C6 alkoxy group, a hydroxy C1-C6 alkylcarbamoyl group, or a hydroxy C1-C6 alkylcarbamoyl C1-C6 alkyl group), the hydroxy group forms an ester bond with a C1-C6 alkanoyl group.

### Claim 25 (depends on 1)

The compound or pharmacologically acceptable salt thereof according to claim 1, selected from the following:
({[5-hydroxy-2-({1-[4′-(hydroxymethyl)biphenyl-4-yl]piperidin-4-yl}methyl)-6-methylpyrimidin-4-yl]carbonyl}amino)acetic acid,
({[2-({1-[4′-(acetoxymethyl)biphenyl-4-yl]piperidin-4-yl}methyl)-5-hydroxy-6-methylpyrimidin-4-yl]carbonyl}amino)acetic acid,
({[5-hydroxy-2-({1-[4′-(1-hydroxyethyl)biphenyl-4-yl]piperidin-4-yl}methyl)-6-methylpyrimidin-4-yl]carbonyl}amino)acetic acid,
({[5-hydroxy-2-({1-[4′-(2-hydroxyethyl)biphenyl-4-yl]piperidin-4-yl}methyl)-6-methylpyrimidin-4-yl]carbonyl}amino)acetic acid,
({[5-hydroxy-2-({1-[4′-(2-hydroxypropyl)biphenyl-4-yl]piperidin-4-yl}methyl)-6-methylpyrimidin-4-yl]carbonyl}amino)acetic acid,
({[5-hydroxy-2-({1-[4′-(2-hydroxy-1,1-dimethylethyl)biphenyl-4-yl]piperidin-4-yl}methyl)-6-methylpyrimidin-4-yl]carbonyl}amino)acetic acid,
({[2-({1-[4′-(dimethylcarbamoyl)biphenyl-4-yl]piperidin-4-yl}methyl)-5-hydroxy-6-methylpyrimidin-4-yl]carbonyl}amino)acetic acid,
({[5-hydroxy-6-methyl-2-({1-[4′-(methylcarbamoyl)biphenyl-4-yl]piperidin-4-yl}methyl)pyrimidin-4-yl]carbonyl}amino)acetic acid,
[({2-[(1-{4′-[2-(dimethylamino)-2-oxoethyl]biphenyl-4-yl}piperidin-4-yl)methyl]-5-hydroxy-6-methylpyrimidin-4-yl}carbonyl)amino]acetic acid,
[({5-hydroxy-2-[(1-{4-[4-(hydroxymethyl)benzyl]phenyl}piperidin-4-yl)methyl]-6-methylpyrimidin-4-yl}carbonyl)amino]acetic acid,
[({5-hydroxy-2-[(1-{4-[3-(hydroxymethyl)benzyl]phenyl}piperidin-4-yl)methyl]-6-methylpyrimidin-4-yl}carbonyl)amino]acetic acid,
[({5-hydroxy-2-[(1-{4-[5-(1-hydroxyethyl)pyridin-2-yl]phenyl}piperidin-4-yl)methyl]-6-methylpyrimidin-4-yl}carbonyl)amino]acetic acid,
{[(5-hydroxy-2-{[1-(4-{5-[1-(methoxymethoxy)ethyl]pyridin-2-yl}phenyl)piperidin-4-yl]methyl}-6-methylpyrimidin-4-yl)carbonyl]amino}acetic acid,
[({2-[(1-{4-[5-(1-acetoxyethyl)pyridin-2-yl]phenyl}piperidin-4-yl)methyl]-5-hydroxy-6-methylpyrimidin-4-yl}carbonyl)amino]acetic acid,
[({5-hydroxy-2-[(1-{4-[5-(hydroxymethyl)pyridin-2-yl]phenyl}piperidin-4-yl)methyl]-6-methylpyrimidin-4-yl}carbonyl)amino]acetic acid,
[({2-[(1-{4-[5-(ethoxycarbonyl)pyridin-2-yl]phenyl}piperidin-4-yl)methyl]-5-hydroxy-6-methylpyrimidin-4-yl}carbonyl)amino]acetic acid,
[({2-[(1-{4-[2-(ethoxycarbonyl)benzyl]phenyl}piperidin-4-yl)methyl]-5-hydroxy-6-methylpyrimidin-4-yl}carbonyl)amino]acetic acid,
{[(5-hydroxy-2-{[1-(4-{[6-(2-hydroxyethoxy)pyridin-3-yl]methyl}phenyl)piperidin-4-yl]methyl}-6-methylpyrimidin-4-yl)carbonyl]amino}acetic acid,
[({5-hydroxy-2-[(1-{5-[4-(hydroxymethyl)phenyl]pyridin-2-yl}piperidin-4-yl)methyl]-6-methylpyrimidin-4-yl}carbonyl)amino]acetic acid,
[({5-hydroxy-2-[(1-{5-[4-(2-hydroxypropyl)phenyl]pyridin-2-yl}piperidin-4-yl)methyl]-6-methylpyrimidin-4-yl}carbonyl)amino]acetic acid,
[({5-hydroxy-2-[(1-{5-[4-(2-hydroxy-1,1-dimethylethyl)phenyl]pyridin-2-yl}piperidin-4-yl)methyl]-6-methylpyrimidin-4-yl}carbonyl)amino]acetic acid,
({[2-({1-[2-chloro-4′-(hydroxymethyl)biphenyl-4-yl]piperidin-4-yl}methyl)-5-hydroxy-6-methylpyrimidin-4-yl]carbonyl}amino)acetic acid,
({[5-hydroxy-2-({1-[4′-(hydroxymethyl)-2-methylbiphenyl-4-yl]piperidin-4-yl}methyl)-6-methylpyrimidin-4-yl]carbonyl}amino)acetic acid,
({[2-({1-[3′-chloro-4′-(hydroxymethyl)biphenyl-4-yl]piperidin-4-yl}methyl)-5-hydroxy-6-methylpyrimidin-4-yl]carbonyl}amino)acetic acid,
({[5-hydroxy-2-({1-[4′-(hydroxymethyl)-2′-methylbiphenyl-4-yl]piperidin-4-yl}methyl)-6-methylpyrimidin-4-yl]carbonyl}amino)acetic acid,
({[5-hydroxy-2-({1-[4′-(hydroxymethyl)-2,3′-dimethylbiphenyl-4-yl]piperidin-4-yl}methyl)-6-methylpyrimidin-4-yl]carbonyl}amino)acetic acid,
({[5-hydroxy-2-({1-[4′-(2-hydroxybutyl)biphenyl-4-yl]piperidin-4-yl}methyl)-6-methylpyrimidin-4-yl]carbonyl}amino)acetic acid,
[({5-hydroxy-2-[(1-{4-[4-(2-hydroxypropyl)benzyl]phenyl}piperidin-4-yl)methyl]-6-methylpyrimidin-4-yl}carbonyl)amino]acetic acid,
[({5-hydroxy-2-[(1-{4-[4-(2-hydroxy-1,1-dimethylethyl)benzyl]phenyl}piperidin-4-yl)methyl]-6-methylpyrimidin-4-yl}carbonyl)amino]acetic acid,
({[2-({1-[4′-(1,1-difluoro-2-hydroxyethyl)biphenyl-4-yl]piperidin-4-yl}methyl)-5-hydroxy-6-methylpyrimidin-4-yl]carbonyl}amino)acetic acid,
({[2-({1-[4′-(1,1-difluoro-2-hydroxypropyl)biphenyl-4-yl]piperidin-4-yl}methyl)-5-hydroxy-6-methylpyrimidin-4-yl]carbonyl}amino)acetic acid,
({[2-({1-[4′-(1,1-difluoro-2-hydroxy-2-methylpropyl)biphenyl-4-yl]piperidin-4-yl}methyl)-5-hydroxy-6-methylpyrimidin-4-yl]carbonyl}amino)acetic acid,
{[(5-[(2,2-dimethylpropanoyl)oxy]-2-{[1-(4′-{[(2,2-dimethylpropanoyl)oxy]methyl}biphenyl-4-yl)piperidin-4-yl]methyl}-6-methylpyrimidin-4-yl)carbonyl]amino}acetic acid,
{[(2-{[1-(4′-{[(2,2-dimethylpropanoyl)oxy]methyl}biphenyl-4-yl)piperidin-4-yl]methyl}-5-hydroxy-6-methylpyrimidin-4-yl)carbonyl]amino}acetic acid,
({[5-hydroxy-2-({1-[4′-(methoxymethyl)biphenyl-4-yl]piperidin-4-yl}methyl)-6-methylpyrimidin-4-yl]carbonyl}amino)acetic acid,
({[2-({1-[2′-fluoro-4′-(hydroxymethyl)biphenyl-4-yl]piperidin-4-yl}methyl)-5-hydroxy-6-methylpyrimidin-4-yl]carbonyl}amino)acetic acid,
({[2-({1-[3′-fluoro-4′-(hydroxymethyl)biphenyl-4-yl]piperidin-4-yl}methyl)-5-hydroxy-6-methylpyrimidin-4-yl]carbonyl}amino)acetic acid,
({[2-({1-[2-fluoro-4′-(hydroxymethyl)biphenyl-4-yl]piperidin-4-yl}methyl)-5-hydroxy-6-methylpyrimidin-4-yl]carbonyl}amino)acetic acid,
({[2-({1-[3-fluoro-4′-(hydroxymethyl)biphenyl-4-yl]piperidin-4-yl}methyl)-5-hydroxy-6-methylpyrimidin-4-yl]carbonyl}amino)acetic acid,
({[5-hydroxy-2-({1-[4′-(hydroxymethyl)-3′-methylbiphenyl-4-yl]piperidin-4-yl}methyl)-6-methylpyrimidin-4-yl]carbonyl}amino)acetic acid,
({[2-({1-[3′,5′-difluoro-4′-(hydroxymethyl)biphenyl-4-yl]piperidin-4-yl}methyl)-5-hydroxy-6-methylpyrimidin-4-yl]carbonyl}amino)acetic acid,
({[2-({1-[3′,5′-dichloro-4′-(hydroxymethyl)biphenyl-4-yl]piperidin-4-yl}methyl)-5-hydroxy-6-methylpyrimidin-4-yl]carbonyl}amino)acetic acid,
({[2-({1-[3′,5′-dimethyl-4′-(hydroxymethyl)biphenyl-4-yl]piperidin-4-yl}methyl)-5-hydroxy-6-methylpyrimidin-4-yl]carbonyl}amino)acetic acid,
[({5-hydroxy-2-[(1-{4′-[2-hydroxy-3-methoxypropyl]biphenyl-4-yl}piperidin-4-yl)methyl]-6-methylpyrimidin-4-yl}carbonyl)amino]acetic acid,
({[5-hydroxy-2-({1-[4′-(3-hydroxypropyl)biphenyl-4-yl]piperidin-4-yl}methyl)-6-methylpyrimidin-4-yl]carbonyl}amino)acetic acid,
({[5-hydroxy-2-({1-[4′-(hydroxymethyl)-3′-isopropylbiphenyl-4-yl]piperidin-4-yl}methyl)-6-methylpyrimidin-4-yl]carbonyl}amino)acetic acid,
[({2-[(1-{5-[3-fluoro-4-(hydroxymethyl)phenyl]pyridin-2-yl}piperidin-4-yl)methyl]-5-hydroxy-6-methylpyrimidin-4-yl}carbonyl)amino]acetic acid,
[({2-[(1-{5-[3-chloro-4-(hydroxymethyl)phenyl]pyridin-2-yl}piperidin-4-yl)methyl]-5-hydroxy-6-methylpyrimidin-4-yl}carbonyl)amino]acetic acid, or
[({5-hydroxy-2-[(1-{5-[4-(hydroxymethyl)-3-methylphenyl]pyridin-2-yl}piperidin-4-yl)methyl]-6-methylpyrimidin-4-yl}carbonyl)amino]acetic acid.

### Claim 26 (depends on 1)

A pharmaceutical composition containing as an active ingredient a compound, pharmacologically acceptable ester thereof, or pharmacologically acceptable salt thereof according to claim 1.

### Claim 27 (depends on 26)

The pharmaceutical composition according to claim 26, for the prophylaxis and/or treatment of anemia.

### Claim 28 (depends on 27)

The pharmaceutical composition according to claim 27, wherein the anemia is nephrogenic anemia, anemia of prematurity, anemia incidental to chronic diseases, anemia incidental to cancer chemotherapy, cancerous anemia, inflammation-associated anemia, or anemia incidental to congestive heart failure.

### Claim 29 (depends on 27)

The pharmaceutical composition according to claim 27, wherein the anemia is anemia incidental to chronic kidney disease.

### Claim 30 (depends on 26)

The pharmaceutical composition according to claim 26, for producing erythropoietin.

### Claim 31 (depends on 1)

A method for producing erythropoietin, comprising: administering a pharmacologically effective amount of a compound, pharmacologically acceptable ester thereof, or pharmacologically acceptable salt thereof according to claim 1 to a mammal or bird.

### Claim 32 (depends on 1)

A method for the treatment of anemia caused by decreased erythropoietin, comprising: administering a pharmacologically effective amount of a compound, pharmacologically acceptable ester thereof, or pharmacologically acceptable salt thereof according to claim 1 to a mammal.

### Claim 33 (depends on 32)

The method according to claim 32, wherein the anemia is nephrogenic anemia, anemia of prematurity, anemia incidental to chronic diseases, anemia incidental to cancer chemotherapy, cancerous anemia, inflammation-associated anemia, or anemia incidental to congestive heart failure.

### Claim 34 (depends on 32)

The method according to claim 32, wherein the anemia is anemia incidental to chronic kidney disease.

### Claim 35 (depends on 32)

A method according to claim 32, wherein the mammal is a human.

### Claim 36 (depends on 1)

The compound or pharmacologically acceptable salt thereof according to claim 1, wherein the compound represented by formula (1) is ({[5-hydroxy-2-({1-[4′-(2-hydroxypropyl)biphenyl-4-yl]piperidin-4-yl}methyl)-6-methylpyrimidin-4-yl]carbonyl}amino)acetic acid.

### Claim 37 (depends on 1)

The compound or pharmacologically acceptable salt thereof according to claim 1, wherein the compound represented by formula (1) is ({[5-hydroxy-2-({1-[4′-((2S)-2-hydroxypropyl)biphenyl-4-yl]piperidin-4-yl}methyl)-6-methylpyrimidin-4-yl]carbonyl}amino)acetic acid.

### Claim 38 (depends on 1)

The compound or pharmacologically acceptable salt thereof according to claim 1, wherein the compound represented by formula (1) is ({[5-hydroxy-2-({1-[4′-((2R)-2-hydroxypropyl)biphenyl-4-yl]piperidin-4-yl}methyl)-6-methylpyrimidin-4-yl]carbonyl}amino)acetic acid.

### Claim 39 (depends on 1)

The compound or pharmacologically acceptable salt thereof according to claim 1, wherein the compound represented by formula (1) is ({[5-hydroxy-2-({1-[4′-(hydroxymethyl)biphenyl-4-yl]piperidin-4-yl}methyl)-6-methylpyrimidin-4-yl]carbonyl}amino)acetic acid.

### Claim 40 (depends on 36)

A pharmaceutical composition containing as an active ingredient a compound, pharmacologically acceptable ester thereof, or pharmacologically acceptable salt thereof according to claim 36.

### Claim 41 (depends on 37)

A pharmaceutical composition containing as an active ingredient a compound, pharmacologically acceptable ester thereof, or pharmacologically acceptable salt thereof according to claim 37.

### Claim 42 (depends on 38)

A pharmaceutical composition containing as an active ingredient a compound, pharmacologically acceptable ester thereof, or pharmacologically acceptable salt thereof according to claim 38.

### Claim 43 (depends on 39)

A pharmaceutical composition containing as an active ingredient a compound, pharmacologically acceptable ester thereof, or pharmacologically acceptable salt thereof according to claim 39.

### Claim 44 (depends on 36)

A method for the treatment of anemia caused by decreased erythropoietin, comprising: administering a pharmacologically effective amount of a compound or pharmacologically acceptable salt thereof according to claim 36 to a human.

### Claim 45 (depends on 44)

The method according to claim 44, wherein the anemia is nephrogenic anemia, anemia of prematurity, anemia incidental to chronic diseases, anemia incidental to cancer chemotherapy, cancerous anemia, inflammation-associated anemia, or anemia incidental to congestive heart failure.

### Claim 46 (depends on 44)

The method according to claim 44, wherein the anemia is anemia incidental to chronic kidney disease.

### Claim 47 (depends on 37)

A method for the treatment of anemia caused by decreased erythropoietin, comprising: administering a pharmacologically effective amount of a compound or pharmacologically acceptable salt thereof according to claim 37 to a human.

### Claim 48 (depends on 47)

The method according to claim 47, wherein the anemia is nephrogenic anemia, anemia of prematurity, anemia incidental to chronic diseases, anemia incidental to cancer chemotherapy, cancerous anemia, inflammation-associated anemia, or anemia incidental to congestive heart failure.

### Claim 49 (depends on 47)

The method according to claim 47, wherein the anemia is anemia incidental to chronic kidney disease.

### Claim 50 (depends on 38)

A method for the treatment of anemia caused by decreased erythropoietin, comprising: administering a pharmacologically effective amount of a compound or pharmacologically acceptable salt thereof according to claim 38 to a human.

### Claim 51 (depends on 50)

The method according to claim 50, wherein the anemia is nephrogenic anemia, anemia of prematurity, anemia incidental to chronic diseases, anemia incidental to cancer chemotherapy, cancerous anemia, inflammation-associated anemia, or anemia incidental to congestive heart failure.

### Claim 52 (depends on 50)

The method according to claim 50, wherein the anemia is anemia incidental to chronic kidney disease.

### Claim 53 (depends on 39)

A method for the treatment of anemia caused by decreased erythropoietin, comprising: administering a pharmacologically effective amount of a compound or pharmacologically acceptable salt thereof according to claim 39 to a human.

### Claim 54 (depends on 53)

The method according to claim 53, wherein the anemia is nephrogenic anemia, anemia of prematurity, anemia incidental to chronic diseases, anemia incidental to cancer chemotherapy, cancerous anemia, inflammation-associated anemia, or anemia incidental to congestive heart failure.

### Claim 55 (depends on 53)

The method according to claim 53, wherein the anemia is anemia incidental to chronic kidney disease.