# US 8,541,585 B2 · N-acyl cyclic amine derivative or pharmaceutically acceptable salt thereof

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- Number: US 8,541,585 B2
- Document ID: US8541585B2
- Status: Granted
- Kind: B2
- Application number: 13/505,161
- Filed: 2011-03-11
- Published: 2012-08-23
- Granted: 2013-09-24
- Earliest claimed: 2010-03-11
- Assignees: Dainippon Sumitomo Pharma Co., Ltd.
- Applicants: Megumi Maruyama; Naoya Kinomura; Satoshi Nojima; Masahiro Takamura; Keisuke Kakiguchi; Hiroto Tatamidani
- Inventors: Megumi Maruyama; Naoya Kinomura; Satoshi Nojima; Masahiro Takamura; Keisuke Kakiguchi; Hiroto Tatamidani
- Web page: https://patentgrep.com/patent/US8541585B2

## CPC

- C07D 413/14: containing three or more hetero rings
- A61P 25/18: Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
- C07D 401/14: containing three or more hetero rings
- C07D 405/14: containing three or more hetero rings
- C07D 409/14: containing three or more hetero rings
- C07D 417/14: 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 compounds which show high effectiveness against positive symptoms, negative symptoms and cognitive dysfunction in schizophrenia and reduce conventional side-effect risks as well as have remarkable effects for central neurological diseases associated with cognitive dysfunction other than schizophrenia. N-Acyl cyclic amine derivatives of formula (1): wherein Ar1 and Ar2 are aryl or heteroaryl; V is nitrogen, or CR3; W1 is a single bond, —C(O)—, etc.; W2 is C1-alkylene; W3 is a single bond, methylene, —NH—, —CR4═CR5—, etc.; Ring Q is a group of formula (a) in which n is 0 or 1; m is 0 to 2; k is 1 to 3; Z is a single bond, methylene, oxygen, etc.; R1a, R1b and R1c are each, same or different, hydrogen, hydroxyl, halogen, cyano, C1-6 alkyl, etc.; or pharmaceutically acceptable salts thereof are provided.

## Claims

### Claim 1

A compound of the following formula (1):
wherein Ar1 and Ar2 are each independently optionally substituted C6-10 aryl or optionally substituted heteroaryl;
V is CR3, in which R3 is hydrogen, hydroxyl, halogen, cyano, or optionally substituted C1-6 alkyl;
W1 is a single bond, oxygen, sulfur, —C(O)— or —NR2—, in which R2 is hydrogen or optionally substituted C1-6 alkyl,
piperidine ring in case that V is CR3 may be each independently optionally substituted by one or more and same or different groups selected from the group consisting of hydroxyl, halogen, cyano, C1-6 alkyl and C1-6 alkoxy on any substituent positions;
W2 is optionally substituted ethylene;
W3 is a single bond, oxygen, sulfur, —NH—, optionally substituted methylene, optionally substituted ethylene, or —CR4═CR5—, in which R4 and R5 are each independently hydrogen, halogen or optionally substituted C1-6 alkyl;
Ring Q is a group of the following formula (a):
in which n is 0;
m is 0, 1 or 2;
k is 1, 2 or 3;
Z is a single bond, methylene, oxygen, sulfur, —S(O)—, —S(O)2— or —NR21—, in which R21 is hydrogen or optionally substituted C1-6 alkyl;
R1a, R1b and R1c are each, same or different, hydrogen, hydroxyl, halogen, cyano, carboxyl, optionally substituted amino, optionally substituted C1-6 alkyl, optionally substituted C3-7 cycloalkyl, optionally substituted C3-7 cycloalkyl-C1-4 alkyl, optionally substituted C7-14 aralkyl, optionally substituted heteroaryl-C1-4 alkyl, optionally substituted saturated heterocyclic C1-4 alkyl, optionally substituted C6-10 aryl, optionally substituted heteroaryl, optionally substituted saturated heterocycle, optionally substituted C1-6 alkoxy, optionally substituted C3-7 cycloalkoxy, optionally substituted C6-10 aryloxy, optionally substituted heteroaryloxy, optionally substituted saturated heterocyclic oxy, optionally substituted C7-14 aralkyloxy, optionally substituted C1-6 alkylcarbonylamino, optionally substituted C3-7 cycloalkylcarbonylamino, optionally substituted C6-10 arylcarbonylamino, optionally substituted saturated heterocyclic carbonylamino, optionally substituted heteroarylcarbonylamino, optionally substituted C1-6 alkylcarbonyloxy, optionally substituted aminocarbonyloxy, optionally substituted C1-6 alkoxycarbonylamino, optionally substituted C3-7 cycloalkoxycarbonylamino, optionally substituted saturated heterocyclic oxycarbonylamino, optionally substituted aminocarbonylamino, optionally substituted aminosulfonylamino, optionally substituted C1-6 alkylsulfonylamino, optionally substituted C3-7 cycloalkylsulfonylamino, optionally substituted C6-10 arylsulfonylamino, optionally substituted saturated heterocyclic sulfonylamino, or optionally substituted heteroarylsulfonylamino,
alternatively, R1a and R1b may combine each other together with the carbon atom to which they bind to form C3-7 cycloalkyl ring, or saturated heterocycle, in which the C3-7 cycloalkyl ring and the saturated heterocycle may be optionally substituted by one or more and same or different groups selected from the group consisting of hydroxyl, halogen, cyano, C1-6 alkyl, C1-6 alkoxy, C6-10 aryl, heteroaryl and 4- to 7-membered saturated heterocycle; or a pharmaceutically acceptable salt thereof.

### Claim 2 (depends on 1)

The compound of claim 1, represented by the following formula (2):
wherein Ar1 and Ar2 are each independently optionally substituted C6-10 aryl or optionally substituted heteroaryl;
W1 is a single bond or —C(O)—;
W3 is a single bond, optionally substituted methylene, optionally substituted ethylene, or —CR4═CR5—, in which R4 and R5 are each independently hydrogen, halogen or optionally substituted C1-6 alkyl;
R3 is hydrogen, hydroxyl, halogen or cyano;
Ring Q is a group of the following formula (a-1):
in which m is 0, 1 or 2;
k is 1, 2 or 3;
Z is a single bond, methylene, oxygen, or —NR21—, in which R21 is hydrogen or optionally substituted C1-6 alkyl;
R1a, R1b and R1c have the same meanings as defined in claim 1; or a pharmaceutically acceptable salt thereof.

### Claim 3 (depends on 1)

The compound of claim 1, wherein Ar1 is any one of groups of the following formulae (b-1) to (b-17):
in which carbon atoms in the groups of the formulae (b-1) to (b-17) may be optionally substituted by one or more and same or different groups selected from the group consisting of halogen, hydroxyl, cyano, C1-6 alkyl and C1-6 alkoxy; or a pharmaceutically acceptable salt thereof.

### Claim 4 (depends on 1)

The compound of claim 1, wherein Ar2 is any one of groups of the following formulae (c-1) to (c-19):
in which carbon atoms in the groups of the formulae (c-1) to (c-19) may be optionally substituted by one or more and same or different groups selected from the group consisting of hydroxyl, halogen, cyano, carboxyl, optionally substituted amino, optionally substituted C1-6 alkyl, optionally substituted C3-7 cycloalkyl, optionally substituted C3-7 cycloalkyl-C1-4 alkyl, optionally substituted C7-14 aralkyl, optionally substituted heteroaryl-C1-4 alkyl, optionally substituted saturated heterocyclic C1-4 alkyl, optionally substituted C6-10 aryl, optionally substituted heteroaryl, optionally substituted saturated heterocycle, optionally substituted C1-6 alkoxy, optionally substituted C1-6 alkylthio, optionally substituted C3-7 cycloalkoxy, optionally substituted C6-10 aryloxy, optionally substituted heteroaryloxy, optionally substituted saturated heterocyclic oxy, optionally substituted C1-6 alkylcarbonylamino, optionally substituted C3-7 cycloalkylcarbonylamino, optionally substituted C6-10 arylcarbonylamino, optionally substituted heteroarylcarbonylamino, optionally substituted saturated heterocyclic carbonylamino, optionally substituted C1-6 alkoxycarbonylamino, optionally substituted C3-7 cycloalkoxycarbonylamino, optionally substituted saturated heterocyclic oxycarbonylamino, optionally substituted aminocarbonylamino, optionally substituted aminosulfonylamino, optionally substituted C1-6 alkylcarbonyl, optionally substituted C3-7 cycloalkylcarbonyl, optionally substituted C3-7 cycloalkyl-C1-4 alkylcarbonyl, optionally substituted C6-10 arylcarbonyl, optionally substituted heteroarylcarbonyl, optionally substituted saturated heterocyclic carbonyl, optionally substituted C1-6 alkoxycarbonyl, optionally substituted C3-7 cycloalkoxycarbonyl, optionally substituted saturated heterocyclic oxycarbonyl, optionally substituted aminocarbonyl, optionally substituted C1-6 alkylsulfonyl, optionally substituted C3-7 cycloalkylsulfonyl, optionally substituted C6-10 arylsulfonyl, optionally substituted heteroarylsulfonyl, optionally substituted saturated heterocyclic sulfonyl and optionally substituted aminosulfonyl;
NH in the groups of the formulae (c-1) to (c-19) may be optionally substituted by one or more and same or different groups selected from the group consisting of optionally substituted C1-6 alkyl, optionally substituted C3-7 cycloalkyl, optionally substituted C3-7 cycloalkyl-C1-4 alkyl, optionally substituted C7-14 aralkyl, optionally substituted heteroaryl-C1-4 alkyl, optionally substituted saturated heterocyclic C1-4 alkyl, optionally substituted C6-10 aryl, optionally substituted heteroaryl, optionally substituted saturated heterocycle, optionally substituted C1-6 alkylcarbonyl, optionally substituted C3-7 cycloalkylcarbonyl, optionally substituted C3-7 cycloalkyl-C1-4 alkylcarbonyl, optionally substituted C1-6 alkoxycarbonyl, optionally substituted C3-7 cycloalkoxycarbonyl, optionally substituted saturated heterocyclic oxycarbonyl, optionally substituted C6-10 arylcarbonyl, optionally substituted heteroarylcarbonyl, optionally substituted saturated heterocyclic carbonyl, optionally substituted aminocarbonyl, optionally substituted C1-6 alkylsulfonyl, optionally substituted C3-7 cycloalkylsulfonyl, optionally substituted C6-10 arylsulfonyl, optionally substituted heteroarylsulfonyl, optionally substituted saturated heterocyclic sulfonyl and optionally substituted aminosulfonyl; or a pharmaceutically acceptable salt thereof.

### Claim 5 (depends on 4)

The compound of claim 4, wherein carbon atoms in the groups of the formulae (c-1) to (c-19) may be optionally substituted by one or more and same or different groups selected from the group consisting of hydroxyl, halogen, cyano, optionally substituted C1-6 alkyl, optionally substituted C7-14 aralkyl, optionally substituted heteroaryl-C1-4 alkyl, optionally substituted saturated heterocyclic C1-4 alkyl, optionally substituted C1-6 alkoxy, optionally substituted C1-6 alkylthio, optionally substituted saturated heterocyclic oxy, optionally substituted C6-10 aryl, optionally substituted heteroaryl, optionally substituted saturated heterocycle, optionally substituted C1-6 alkylcarbonyl, optionally substituted C3-7 cycloalkylcarbonyl, optionally substituted C3-7 cycloalkyl-C1-4 alkylcarbonyl, optionally substituted C6-10 arylcarbonyl, optionally substituted heteroarylcarbonyl, optionally substituted saturated heterocyclic carbonyl, optionally substituted aminocarbonyl, optionally substituted C1-6 alkylsulfonyl, optionally substituted C3-7 cycloalkylsulfonyl, optionally substituted C6-10 arylsulfonyl, optionally substituted heteroarylsulfonyl, optionally substituted saturated heterocyclic sulfonyl and optionally substituted aminosulfonyl;
NH in the groups of the formulae (c-1) to (c-19) may be optionally substituted by one or more and same or different groups selected from the group consisting of optionally substituted C1-6 alkyl, optionally substituted C3-7 cycloalkyl, optionally substituted C3-7 cycloalkyl-C1-4 alkyl, optionally substituted saturated heterocyclic C1-4 alkyl, optionally substituted C6-10 aryl, optionally substituted heteroaryl, optionally substituted saturated heterocycle, optionally substituted C1-6 alkylcarbonyl, optionally substituted C3-7 cycloalkylcarbonyl, optionally substituted C3-7 cycloalkyl-C1-4 alkylcarbonyl, optionally substituted C1-6 alkoxycarbonyl, optionally substituted C3-7 cycloalkoxycarbonyl, optionally substituted saturated heterocyclic oxycarbonyl, optionally substituted C6-10 arylcarbonyl, optionally substituted heteroarylcarbonyl, optionally substituted saturated heterocyclic carbonyl, optionally substituted aminocarbonyl, optionally substituted C1-6 alkylsulfonyl, optionally substituted C3-7 cycloalkylsulfonyl, optionally substituted C6-10 arylsulfonyl, optionally substituted heteroarylsulfonyl, optionally substituted saturated heterocyclic sulfonyl and optionally substituted aminosulfonyl; or a pharmaceutically acceptable salt thereof.

### Claim 6 (depends on 1)

The compound of claim 1, wherein R1a, R1b and R1c are each, same or different, hydrogen, hydroxyl, halogen, cyano, optionally substituted C1-6 alkyl, optionally substituted C3-7 cycloalkyl, optionally substituted C3-7 cycloalkyl-C1-4 alkyl, optionally substituted C7-14 aralkyl, optionally substituted heteroaryl-C1-4 alkyl, optionally substituted saturated heterocyclic C1-4 alkyl, optionally substituted C6-10 aryl, optionally substituted heteroaryl, optionally substituted saturated heterocycle, optionally substituted C1-6 alkoxy, optionally substituted C3-7 cycloalkoxy, optionally substituted C6-10 aryloxy, optionally substituted heteroaryloxy, optionally substituted saturated heterocyclic oxy, optionally substituted C7-14 aralkyloxy, optionally substituted C1-6 alkylcarbonyloxy, or optionally substituted aminocarbonyloxy,
alternatively, R1a and R1b may combine each other together with the carbon atom to which they bind to form C3-7 cycloalkyl ring, or saturated heterocycle, in which the C3-7 cycloalkyl ring and the saturated heterocycle may be optionally substituted by one or more and same or different groups selected from the group consisting of hydroxyl, halogen and cyano; or a pharmaceutically acceptable salt thereof.

### Claim 7 (depends on 1)

The compound of claim 1, wherein Ring Q is any one of rings of the following formulae (a-2) to (a-7):
in which R1a, R1b and R1c are each, same or different, hydrogen, hydroxyl, halogen, cyano, optionally substituted C1-6 alkyl, optionally substituted C3-7 cycloalkyl, optionally substituted C3-7 cycloalkyl-C1-4 alkyl, optionally substituted C7-14 aralkyl, optionally substituted heteroaryl-C1-4 alkyl, optionally substituted saturated heterocyclic C1-4 alkyl, optionally substituted C6-10 aryl, optionally substituted heteroaryl, optionally substituted saturated heterocycle, optionally substituted C1-6 alkoxy, optionally substituted C3-7 cycloalkoxy, optionally substituted C6-10 aryloxy, optionally substituted heteroaryloxy, optionally substituted saturated heterocyclic oxy, optionally substituted C7-14 aralkyloxy, optionally substituted C1-6 alkylcarbonyloxy, or optionally substituted aminocarbonyloxy,
alternatively, R1a and R1b may combine each other together with the carbon atom to which they bind to form C3-7 cycloalkyl ring, or saturated heterocycle, in which the C3-7 cycloalkyl ring and the saturated heterocycle may be optionally substituted by one or more and same or different groups selected from the group consisting of hydroxyl, halogen and cyano; or a pharmaceutically acceptable salt thereof.

### Claim 8 (depends on 1)

The compound of claim 1, wherein Ar1 is any one of groups of the following formulae (b-1) to (b-4):
in which carbon atoms in the groups of the formulae may be optionally substituted by one or more and same or different groups selected from the group consisting of halogen, hydroxyl, cyano, C1-6 alkyl and C1-6 alkoxy; or a pharmaceutically acceptable salt thereof.

### Claim 9 (depends on 1)

The compound of claim 1, wherein Ar2 is any one of groups of the following formulae (c-1) to (c-3):
in which carbon atoms in the groups may be optionally substituted by one or more and same or different groups selected from the group consisting of hydroxyl, halogen, cyano, optionally substituted C1-6 alkyl, optionally substituted C7-14 aralkyl, optionally substituted heteroaryl-C1-4 alkyl, optionally substituted saturated heterocyclic C1-4 alkyl, optionally substituted C1-6 alkoxy, optionally substituted C1-6alkylthio, optionally substituted saturated heterocyclic oxy, optionally substituted C6-10 aryl, optionally substituted heteroaryl, optionally substituted saturated heterocycle, optionally substituted C1-6 alkylcarbonyl, optionally substituted C3-7 cycloalkylcarbonyl, optionally substituted C3-7 cycloalkyl-C1-4alkylcarbonyl, optionally substituted C6-10 arylcarbonyl, optionally substituted heteroarylcarbonyl, optionally substituted saturated heterocyclic carbonyl, optionally substituted aminocarbonyl, optionally substituted C1-6 alkylsulfonyl, optionally substituted C3-7 cycloalkylsulfonyl, optionally substituted C6-10 arylsulfonyl, optionally substituted heteroarylsulfonyl, optionally substituted saturated heterocyclic sulfonyl and optionally substituted aminosulfonyl;
and in which the NH in the groups may be optionally substituted by one or more and same or different groups selected from the group consisting of optionally substituted C1-6 alkyl, optionally substituted C3-7 cycloalkyl, optionally substituted C3-7 cycloalkyl-C1-4 alkyl, optionally substituted saturated heterocyclic C1-4 alkyl, optionally substituted C6-10 aryl, optionally substituted heteroaryl, optionally substituted saturated heterocycle, optionally substituted C1-6 alkylcarbonyl, optionally substituted C3-7 cycloalkylcarbonyl, optionally substituted C3-7 cycloalkyl-C1-4 alkylcarbonyl, optionally substituted C1-6 alkoxycarbonyl, optionally substituted C3-7 cycloalkoxycarbonyl, optionally substituted saturated heterocyclic oxycarbonyl, optionally substituted C6-10 arylcarbonyl, optionally substituted heteroarylcarbonyl, optionally substituted saturated heterocyclic carbonyl, optionally substituted aminocarbonyl, optionally substituted C1-6 alkylsulfonyl, optionally substituted C3-7 cycloalkylsulfonyl, optionally substituted C6-10 arylsulfonyl, optionally substituted heteroarylsulfonyl, optionally substituted saturated heterocyclic sulfonyl and optionally substituted aminosulfonyland; or a pharmaceutically acceptable salt thereof.

### Claim 10 (depends on 7)

The compound of claim 7, wherein Ring Q is a group of formula (a-3) of claim 7, or a pharmaceutically acceptable salt thereof.

### Claim 11 (depends on 1)

The compound of claim 1, wherein W3 is a single bond, V is CH, or a pharmaceutically acceptable salt thereof.

### Claim 12 (depends on 1)

The compound of claim 1, represented by the following formula (3):
wherein Ar1 is any one of groups of the following formulae (b-1′), (b-2′), (b-3′) or (b-4′):
in which R17 is hydrogen or halogen;
W1 is a single bond or —C(O)—;
R1a, R1b and R1c are each, same or different, hydrogen, hydroxyl, halogen, cyano, optionally substituted C1-6 alkyl, optionally substituted C3-7 cycloalkyl, optionally substituted C3-7 cycloalkyl-C1-4 alkyl, optionally substituted C7-14 aralkyl, optionally substituted heteroaryl-C1-4 alkyl, optionally substituted saturated heterocyclic C1-4 alkyl, optionally substituted C6-10 aryl, optionally substituted heteroaryl, optionally substituted saturated heterocycle, optionally substituted C1-6 alkoxy, optionally substituted C3-7 cycloalkoxy, optionally substituted C6-10 aryloxy, optionally substituted heteroaryloxy, optionally substituted saturated heterocyclic oxy, optionally substituted C7-14 aralkyloxy, optionally substituted C1-6 alkylcarbonyloxy, or optionally substituted aminocarbonyloxy,
alternatively, R1a and R1b may combine each other together with the carbon atom to which they bind to form C3-7 cycloalkyl ring, or saturated heterocycle, in which the C3-7 cycloalkyl ring and the saturated heterocycle may be optionally substituted by one or more and same or different groups selected from the group consisting of hydroxyl, halogen and cyano;
R11 is selected from the group consisting of optionally substituted C1-6 alkyl, optionally substituted C3-7 cycloalkyl, optionally substituted C3-7 cycloalkyl-C1-4 alkyl, optionally substituted saturated heterocyclic C1-4 alkyl, optionally substituted C6-10 aryl, optionally substituted heteroaryl, optionally substituted saturated heterocycle, optionally substituted C1-6 alkylcarbonyl, optionally substituted C3-7 cycloalkylcarbonyl, optionally substituted C3-7 cycloalkyl-C1-4 alkylcarbonyl, optionally substituted C1-6 alkoxycarbonyl, optionally substituted C3-7 cycloalkoxycarbonyl, optionally substituted saturated heterocyclic oxycarbonyl, optionally substituted C6-10 arylcarbonyl, optionally substituted heteroarylcarbonyl, optionally substituted saturated heterocyclic carbonyl, optionally substituted aminocarbonyl, optionally substituted C1-6 alkylsulfonyl, optionally substituted C3-7 cycloalkylsulfonyl, optionally substituted C6-10 arylsulfonyl, optionally substituted heteroarylsulfonyl, optionally substituted saturated heterocyclic sulfonyl and optionally substituted aminosulfonyl;
R12, R13, R14, R15 and R16 are the same or different groups selected from the group consisting of hydroxyl, halogen, cyano, optionally substituted C1-6 alkyl, optionally substituted C7-14 aralkyl, optionally substituted heteroaryl-C1-4 alkyl, optionally substituted saturated heterocyclic C1-4 alkyl, optionally substituted C1-6 alkoxy, optionally substituted C1-6 alkylthio, optionally substituted saturated heterocyclic oxy, optionally substituted C6-10 aryl, optionally substituted heteroaryl, optionally substituted saturated heterocycle, optionally substituted C1-6 alkylcarbonyl, optionally substituted C3-7 cycloalkylcarbonyl, optionally substituted C3-7 cycloalkyl-C1-4 alkylcarbonyl, optionally substituted C6-10 arylcarbonyl, optionally substituted heteroarylcarbonyl, optionally substituted saturated heterocyclic carbonyl, optionally substituted aminocarbonyl, optionally substituted C1-6 alkylsulfonyl, optionally substituted C3-7 cycloalkylsulfonyl, optionally substituted C6-10 arylsulfonyl, optionally substituted heteroarylsulfonyl, optionally substituted saturated heterocyclic sulfonyl and optionally substituted aminosulfonyl; or a pharmaceutically acceptable salt thereof.

### Claim 13 (depends on 1)

The compound of claim 1, represented by the following formula (4):
wherein Ar1 is any one of groups of the formulae (b-1′), (b-2′), (b-3′) or (b-4′):
in which R17 is hydrogen or halogen;
W1 is a single bond or —C(O)—;
R1a, R1b and R1c are each, same or different, hydrogen, hydroxyl, halogen, cyano, optionally substituted C1-6 alkyl, optionally substituted C3-7 cycloalkyl, optionally substituted C3-7 cycloalkyl-C1-4 alkyl, optionally substituted C7-14 aralkyl, optionally substituted heteroaryl-C1-4 alkyl, optionally substituted saturated heterocyclic C1-4 alkyl, optionally substituted C6-10 aryl, optionally substituted heteroaryl, optionally substituted saturated heterocycle, optionally substituted C1-6 alkoxy, optionally substituted C3-7 cycloalkoxy, optionally substituted C6-10 aryloxy, optionally substituted heteroaryloxy, optionally substituted saturated heterocyclic oxy, optionally substituted C7-14 aralkyloxy, optionally substituted C1-6 alkylcarbonyloxy, or optionally substituted aminocarbonyloxy,
alternatively, R1a and R1b may combine each other together with the carbon atom to which they bind to form C3-7 cycloalkyl ring, or saturated heterocycle, in which the C3-7 cycloalkyl ring and the saturated heterocycle may be optionally substituted by one or more and same or different groups selected from the group consisting of hydroxyl, halogen and cyano;
R11 is selected from the group consisting of optionally substituted C1-6 alkyl, optionally substituted C3-7 cycloalkyl, optionally substituted C3-7 cycloalkyl-C1-4 alkyl, optionally substituted saturated heterocyclic C1-4 alkyl, optionally substituted C6-10 aryl, optionally substituted heteroaryl, optionally substituted saturated heterocycle, optionally substituted C1-6 alkylcarbonyl, optionally substituted C3-7 cycloalkylcarbonyl, optionally substituted C3-7 cycloalkyl-C1-4 alkylcarbonyl, optionally substituted C1-6 alkoxycarbonyl, optionally substituted C3-7 cycloalkoxycarbonyl, optionally substituted saturated heterocyclic oxycarbonyl, optionally substituted C6-10 arylcarbonyl, optionally substituted heteroarylcarbonyl, optionally substituted saturated heterocyclic carbonyl, optionally substituted aminocarbonyl, optionally substituted C1-6 alkylsulfonyl, optionally substituted C3-7 cycloalkylsulfonyl, optionally substituted C6-10 arylsulfonyl, optionally substituted heteroarylsulfonyl, optionally substituted saturated heterocyclic sulfonyl and optionally substituted aminosulfonyl;
R12 and R13 are the same or different groups selected from the group consisting of hydroxyl, halogen, cyano, optionally substituted C1-6 alkyl, optionally substituted C7-14 aralkyl, optionally substituted heteroaryl-C1-4 alkyl, optionally substituted saturated heterocyclic C1-4 alkyl, optionally substituted C1-6 alkoxy, optionally substituted C1-6 alkylthio, optionally substituted saturated heterocyclic oxy, optionally substituted C6-10 aryl, optionally substituted heteroaryl, optionally substituted saturated heterocycle, optionally substituted C1-6 alkylcarbonyl, optionally substituted C3-7 cycloalkylcarbonyl, optionally substituted C3-7 cycloalkyl-C1-4 alkylcarbonyl, optionally substituted C6-10 arylcarbonyl, optionally substituted heteroarylcarbonyl, optionally substituted saturated heterocyclic carbonyl, optionally substituted aminocarbonyl, optionally substituted C1-6 alkylsulfonyl, optionally substituted C3-7 cycloalkylsulfonyl, optionally substituted C6-10 arylsulfonyl, optionally substituted heteroarylsulfonyl, optionally substituted saturated heterocyclic sulfonyl and optionally substituted aminosulfonyl; or a pharmaceutically acceptable salt thereof.

### Claim 14 (depends on 1)

The compound of claim 1, represented by the following formula (5):
wherein Ar1 is any one of the formulae (b-1′), (b-2′), (b-3′) or (b-4′):
in which R17 is hydrogen or halogen;
W1 is a single bond or —C(O)—;
R1a, R1b and R1c are each, same or different, hydrogen, hydroxyl, halogen, cyano, optionally substituted C1-6 alkyl, optionally substituted C3-7 cycloalkyl, optionally substituted C3-7 cycloalkyl-C1-4 alkyl, optionally substituted C7-14 aralkyl, optionally substituted heteroaryl-C1-4 alkyl, optionally substituted saturated heterocyclic C1-4 alkyl, optionally substituted C6-10 aryl, optionally substituted heteroaryl, optionally substituted saturated heterocycle, optionally substituted C1-6 alkoxy, optionally substituted C3-7 cycloalkoxy, optionally substituted C6-10 aryloxy, optionally substituted heteroaryloxy, optionally substituted saturated heterocyclic oxy, optionally substituted C7-14 aralkyloxy, optionally substituted C1-6 alkylcarbonyloxy, or optionally substituted aminocarbonyloxy,
alternatively, R1a and R1b may combine each other together with the carbon atom to which they bind to form C3-7 cycloalkyl ring, or saturated heterocycle, in which the C3-7 cycloalkyl ring and the saturated heterocycle may be optionally substituted by one or more and same or different groups selected from the group consisting of hydroxyl, halogen and cyano;
R11 is selected from the group consisting of optionally substituted C1-6 alkyl, optionally substituted C3-7 cycloalkyl, optionally substituted C3-7 cycloalkyl-C1-4 alkyl, optionally substituted saturated heterocyclic C1-4 alkyl, optionally substituted C6-10 aryl, optionally substituted heteroaryl, optionally substituted saturated heterocycle, optionally substituted C1-6 alkylcarbonyl, optionally substituted C3-7 cycloalkylcarbonyl, optionally substituted C3-7 cycloalkyl-C1-4 alkylcarbonyl, optionally substituted C1-6 alkoxycarbonyl, optionally substituted C3-7 cycloalkoxycarbonyl, optionally substituted saturated heterocyclic oxycarbonyl, optionally substituted C6-10 arylcarbonyl, optionally substituted heteroarylcarbonyl, optionally substituted saturated heterocyclic carbonyl, optionally substituted aminocarbonyl, optionally substituted C1-6 alkylsulfonyl, optionally substituted C3-7 cycloalkylsulfonyl, optionally substituted C6-10 arylsulfonyl, optionally substituted heteroarylsulfonyl, optionally substituted saturated heterocyclic sulfonyl and optionally substituted aminosulfonyl;
R12, R13, R14, and R16 are the same or different groups selected from the group consisting of hydroxyl, halogen, cyano, optionally substituted C1-6 alkyl, optionally substituted C7-14 aralkyl, optionally substituted heteroaryl-C1-4 alkyl, optionally substituted saturated heterocyclic C1-4 alkyl, optionally substituted C1-6 alkoxy, optionally substituted C1-6 alkylthio, optionally substituted saturated heterocyclic oxy, optionally substituted C6-10 aryl, optionally substituted heteroaryl, optionally substituted saturated heterocycle, optionally substituted C1-6 alkylcarbonyl, optionally substituted C3-7 cycloalkylcarbonyl, optionally substituted C3-7 cycloalkyl-C1-4 alkylcarbonyl, optionally substituted C6-10 arylcarbonyl, optionally substituted heteroarylcarbonyl, optionally substituted saturated heterocyclic carbonyl, optionally substituted aminocarbonyl, optionally substituted C1-6 alkylsulfonyl, optionally substituted C3-7 cycloalkylsulfonyl, optionally substituted C6-10 arylsulfonyl, optionally substituted heteroarylsulfonyl, optionally substituted saturated heterocyclic sulfonyl and optionally substituted aminosulfonyl; or a pharmaceutically acceptable salt thereof.

### Claim 15 (depends on 1)

The compound of claim 1, selected from the group consisting of:
(S)-(2-(2-(4-(4-fluorobenzoyl)piperidin-1-yl)ethyl)pyrrolidin-1-yl)(6-methyl-1H-indol-2-yl)methanone;
(S)-(6-fluoro-1H-indol-2-yl)(2-(2-(4-(4-fluorobenzoyl)piperidin-1-yl)ethyl)pyrrolidin-1-yl)methanone;
(S)-(2-(2-(4-(4-fluorobenzoyl)piperidin-1-yl)ethyl)pyrrolidin-1-yl)(6-(trifluoromethoxy)-1H-indol-2-yl)methanone;
(S)-(2-(2-(4-(4-fluorobenzoyl)piperidin-1-yl)ethyl)pyrrolidin-1-yl)(6-isopropyl-1H-indol-2-yl)methanone;
(S)-(5-fluoro-4-methoxy-1H-indol-2-yl)(2-(2-(4-(4-fluorobenzoyl)piperidin-1-yl)ethyl)-pyrrolidin-1-yl)methanone;
(S)-(3,6-difluoro-1H-indol-2-yl)(2-(2-(4-(4-fluorobenzoyl)piperidin-1-yl)ethyl)pyrrolidin-1-yl)methanone;
(S)-(3-fluoro-6-(trifluoromethoxy)-1H-indol-2-yl)(2-(2-(4-(4-fluorobenzoyl)piperidin-1-yl)ethyl)pyrrolidin-1-yl)methanone;
(S)-(3-fluoro-1H-indol-2-yl)(2-(2-(4-(4-fluorobenzoyl)piperidin-1-yl)ethyl)pyrrolidin-1-yl)methanone;
((2S,5S)-2-(2-(4-(4-fluorobenzoyl)piperidin-1-yl)ethyl)-5-methylpyrrolidin-1-yl)(6-methyl-1H-indol-2-yl)methanone;
((2S,5S)-2-(2-(4-(4-fluorobenzoyl)piperidin-1-yl)ethyl)-5-methylpyrrolidin-1-yl)(6-(trifluoro-methyl)-1H-indol-2-yl)methanone;
((2S,5S)-2-(2-(4-(4-fluorobenzoyl)piperidin-1-yl)ethyl)-5-methylpyrrolidin-1-yl)(6-(trifluoro-methylthio)-1H-indol-2-yl)methanone;
(S)-(2-(2-(4-(4-fluorobenzoyl)piperidin-1-yl)ethyl)pyrrolidin-1-yl)(1-methyl-1H-indol-5-yl)methanone and
(S)-(2-(2-(4-(6-fluorobenzo[d]isoxazol-3-yl)piperidin-1-yl)ethyl)pyrrolidin-1-yl)(3-phenyl-1H-pyrazol-5-yl)methanone; or a pharmaceutically acceptable salt thereof.

### Claim 16

(S)-(2-(2-(4-(4-Fluorobenzoyl)piperidin-1-yl)ethyl)pyrrolidin-1-yl)(6-methyl-1H-indol-2-yl)methanone.

### Claim 17

(S)-(6-Fluoro-1H-indol-2-yl)(2-(2-(4-(4-fluorobenzoyl)piperidin-1-yl)ethyl)pyrrolidin-1-yl)methanone.

### Claim 18

(S)-(5-Fluoro-4-methoxy-1H-indol-2-yl)(2-(2-(4-(4-fluorobenzoyl)piperidin-1-yl)ethyl)pyrrolidin-1-yl)methanone.

### Claim 19

(S)-(3,6-Difluoro-1H-indol-2-yl)(2-(2-(4-(4-fluorobenzoyl)piperidin-1-yl)ethyl)pyrrolidin-1-yl)methanone.

### Claim 20

(S)-(3-Fluoro-6-(trifluoromethoxy)-1H-indol-2-yl)(2-(2-(4-(4-fluorobenzoyl)piperidin-1-yl)ethyl)pyrrolidin-1-yl)methanone.

### Claim 21

(S)-(3-Fluoro-1H-indol-2-yl)(2-(2-(4-(4-fluorobenzoyl)piperidin-1-yl)ethyl)pyrrolidin-1-yl)methanone hydrochloride.

### Claim 22 (depends on 1)

A therapeutic agent for schizophrenia, comprising a compound of claim 1 or a pharmaceutically acceptable salt thereof.

### Claim 23 (depends on 1)

A method for treating schizophrenia, comprising administering a therapeutically effective amount of a compound of claim 1 or a pharmaceutically acceptable salt thereof to a mammal in need thereof.