# US 11,028,068 B2 · Somatostatin modulators and uses thereof

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- Number: US 11,028,068 B2
- Document ID: US11028068B2
- Status: Granted
- Kind: B2
- Application number: 16/631,423
- Filed: 2018-07-24
- Published: 2020-07-02
- Granted: 2021-06-08
- Earliest claimed: 2017-07-25
- Assignees: Crinetics Pharmaceuticals, Inc.
- Applicants: Crinetics Pharmaceuticals, Inc.
- Inventors: Jian Zhao; Yunfei Zhu; Shimiao Wang; Sangdon Han; Sun Hee Kim
- Web page: https://patentgrep.com/patent/US11028068B2

## CPC

- C07D 401/12: linked by a chain containing hetero atoms as chain links
- C07D 215/50: attached in position 4
- C07D 401/14: containing three or more hetero rings
- C07D 413/12: linked by a chain containing hetero atoms as chain links
- C07D 413/14: containing three or more hetero rings
- C07D 471/04: Ortho-condensed systems
- A61K 9/0053: {Mouth and digestive tract, i.e. intraoral and peroral administration}
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)

## Abstract

Described herein are compounds that are somatostatin modulators, methods of making such compounds, pharmaceutical compositions and medicaments comprising such compounds, and methods of using such compounds in the treatment of conditions, diseases, or disorders that would benefit from modulation of somatostatin activity.

## Claims

### Claim 1

A compound that has the structure of Formula (I), or a pharmaceutically acceptable salt, solvate, diastereomeric mixture, or individual enantiomers thereof:
wherein:
R1 and R2 are taken together with the carbon atom to which they are attached to form —C(═O)—;
or R1 and R2 are each independently selected from the group consisting of hydrogen, and unsubstituted or substituted C1-C6alkyl;
RA is a cyclic ring that is an unsubstituted or substituted monocyclic carbocycle, unsubstituted or substituted bicyclic carbocycle, unsubstituted or substituted monocyclic heterocycle, or unsubstituted or substituted bicyclic heterocycle, wherein if RA is substituted then RA is substituted with 1-2 R10 and 0-2 R11;
RB is a cyclic ring that is an unsubstituted or substituted monocyclic carbocycle, unsubstituted or substituted bicylcic carbocycle, unsubstituted or substituted monocyclic heterocycle, unsubstituted or substituted bicyclic heterocycle, wherein if RB is substituted then RB is substituted with 1-2 R12 and 0-2 R13;
A1, A2, and A3 are independently CRC or N;
each RC is independently hydrogen, F, Cl, Br, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, sec-butyl, tert-butyl, monofluoromethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, trifluoromethoxy, —CN, —OH, —CO2R14, —C(═O)NR14R15, —C(═NOR14)R15, —SR14, —S(═O)(C1-C4alkyl), —SO2(C1-C4alkyl) or —SO2NR14R15;
R3 and R4 are independently hydrogen, unsubstituted or substituted C1-C6 alkyl, unsubstituted or substituted C1-C6fluoroalkyl, or unsubstituted or substituted C3-C6cycloalkyl, wherein any substituted group of R3 and R4 is substituted with 1-4 R16;
or R3 and R4 are taken together with the nitrogen atom to which they are attached to form an unsubstituted or substituted monocyclic or bicyclic heterocyclic ring, wherein if the heterocyclic ring is substituted then the heterocyclic ring is substituted with 1-4 R16;
R5, R6, R7, and R8 are each independently selected from the group consisting of hydrogen, unsubstituted or substituted C1-C6 alkyl, unsubstituted or substituted C1-C6fluoroalkyl, unsubstituted or substituted monocyclic carbocycle, and unsubstituted or substituted monocyclic heterocycle, wherein any substituted group of R5, R6, R7, and R8 is substituted with 1-4 R16;
R9 is hydrogen, unsubstituted or substituted C1-C6 alkyl, unsubstituted or substituted benzyl, wherein if R9 is substituted then R9 is substituted with 1-4 R16;
or R4 and any one of R5, R7, or R9 are taken together with the intervening atoms to which they are attached to form an unsubstituted or substituted monocyclic 4- to 7-membered heterocyclic ring or an unsubstituted or substituted bicyclic 9- to 12-membered heterocyclic ring, wherein if the heterocyclic ring is substituted then the heterocyclic ring is substituted with 1-4 R16;
or R5 and any one of R6, R7 or R9 are taken together with the intervening atoms to which they are attached to form an unsubstituted or substituted monocyclic 4- to 7-membered ring or a bicyclic 9- to 12-membered ring, wherein if the heterocyclic ring is substituted then the heterocyclic ring is substituted with 1-4 R16;
or R7 and R9 are taken together with the intervening atoms to which they are attached to form an unsubstituted or substituted monocyclic 4- to 7-membered heterocyclic ring or an unsubstituted or substituted bicyclic 9- to 12-membered heterocyclic ring, wherein if the heterocyclic ring is substituted then the heterocyclic ring is substituted with 1-4 R16;
each R10, R11, R12 and R13 is independently hydrogen, halogen, unsubstituted or substituted C1-C4alkyl, unsubstituted or substituted C1-C4alkoxy, unsubstituted or substituted C1-C4fluoroalkyl, unsubstituted or substituted C1-C4fluoroalkoxy, unsubstituted or substituted monocyclic carbocycle, unsubstituted or substituted monocyclic heterocycle, —CN, —OH, —CO2R14, —CH2CO2R14, —C(═O)NR14R15, —CH2C(═O)NR14R15, —NR14R15, —CH2NR14R15, —NR14C(═O)R15, —CH2NR14C(═O)R15, —SR14, —S(═O)R15, —SO2R15, or —SO2NR14R15, wherein if any group of R10, R11, R12 and R13 is substituted then the substituted group of R10, R11, R12 and R13 is substituted with 1-4 R16;
each R16 is independently halogen, C1-C6alkyl, heterocycle, —CN, —OR14, —CO2R14, —C(═O)NR14R15, —NR14R15, —NR14C(═O)R15, —SR14, —S(═O)R15, —SO2R15, or —SO2NR14R15;
each R14 is independently selected from H, unsubstituted or substituted C1-C6alkyl, unsubstituted or substituted C1-C6heteroalkyl, unsubstituted or substituted C3-C10cycloalkyl, substituted or unsubstituted C2-C10heterocycloalkyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl;
each R15 is independently selected from H, unsubstituted or substituted C1-C6alkyl, unsubstituted or substituted C1-C6heteroalkyl, unsubstituted or substituted C3-C10cycloalkyl, substituted or unsubstituted C2-C10heterocycloalkyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl; or R14 and R15 are taken together with the N atom to which they are attached to a substituted or unsubstituted N-containing heterocycle; and
m is 1, 2, 3, or 4.

### Claim 2 (depends on 1)

The compound of claim 1, or a pharmaceutically acceptable salt, solvate, diastereomeric mixture, or individual enantiomers thereof, wherein:
R1 and R2 are taken together with the carbon atom to which they are attached to form —C(═O)—; and
m is 1 or 2.

### Claim 3 (depends on 1)

The compound of claim 1, or a pharmaceutically acceptable salt, solvate, diastereomeric mixture, or individual enantiomers thereof, wherein:
A1, A2, and A3 are CRC;
or A1 is N; and A2 and A3 are CRC;
or A1 and A3 are CRC; and A2 is N;
or A1 and A2 are CRC; and A3 is N;
or A1 and A2 are N; and A3 is CRC;
or A1 and A3 are N; and A2 is CRC.

### Claim 4 (depends on 1)

The compound of claim 1, or a pharmaceutically acceptable salt, solvate, diastereomeric mixture, or individual enantiomers thereof, wherein:
R3 and R4 are each independently selected from the group consisting of hydrogen, unsubstituted or substituted C1-C6 alkyl, and unsubstituted or substituted C1-C6fluoroalkyl, wherein any substituted group of R3 and R4 is substituted with 1-4 R16.

### Claim 5 (depends on 1)

The compound of claim 1, wherein the compound of Formula (I) has the structure of Formula (Ia), Formula (Ib), Formula (Ic), Formula (Id), Formula (Ie), or Formula (If), or a pharmaceutically acceptable salt, solvate, diastereomeric mixture, or individual enantiomers thereof:

### Claim 6 (depends on 1)

The compound of claim 1, or a pharmaceutically acceptable salt, solvate, diastereomeric mixture, or individual enantiomers thereof, wherein:
RA is an unsubstituted or substituted phenyl, wherein if RA is substituted then RA is substituted with 1-2 R10 and 0-2 R11; and
RB is an unsubstituted or substituted phenyl, wherein if RB is substituted then RB is substituted with 1-2 R12 and 0-2 R13.

### Claim 7 (depends on 1)

The compound of claim 1, or a pharmaceutically acceptable salt, solvate, diastereomeric mixture, or individual enantiomers thereof, wherein:
RA is
RB is
n is 0, 1, or 2; and
t is 0, 1, or 2.

### Claim 8 (depends on 1)

The compound of claim 1, or a pharmaceutically acceptable salt, solvate, diastereomeric mixture, or individual enantiomers thereof, wherein:
RA is
and
RB is

### Claim 9 (depends on 1)

The compound of claim 1, or a pharmaceutically acceptable salt, solvate, diastereomeric mixture, or individual enantiomers thereof, wherein:
each R10 is independently hydrogen, halogen, unsubstituted or substituted C1-C4alkyl, unsubstituted or substituted C1-C4alkoxy, unsubstituted or substituted C1-C4fluoroalkyl, unsubstituted or substituted C1-C4fluoroalkoxy, unsubstituted or substituted monocyclic carbocycle, unsubstituted or substituted monocyclic heterocycle, —CN, —OH, —CO2R14, —CH2CO2R14, —C(═O)NR14R15, —CH2C(═O)NR14R15, —NR14R15, —CH2NR14R15, —NR14C(═O)R15, —CH2NR14C(═O)R15, —SR14, —S(═O)R15, —SO2R15, or —SO2NR14R15, wherein if R10 is substituted then R10 is substituted with 1-4 R16;
each R11 is independently hydrogen, halogen, unsubstituted or substituted C1-C4alkyl, unsubstituted or substituted C1-C4alkoxy, unsubstituted or substituted C1-C4fluoroalkyl, unsubstituted or substituted C1-C4fluoroalkoxy, —CN, or —OH, wherein if R11 is substituted then R11 is substituted with 1-4 R16;
each R12 is independently hydrogen, halogen, unsubstituted or substituted C1-C4alkyl, unsubstituted or substituted C1-C4alkoxy, unsubstituted or substituted C1-C4fluoroalkyl, unsubstituted or substituted C1-C4fluoroalkoxy, unsubstituted or substituted monocyclic carbocycle, unsubstituted or substituted monocyclic heterocycle, —CN, —OH, —CO2R14, —CH2CO2R14, —C(═O)NR14R15, —CH2C(═O)NR14R15, —NR14R15, —CH2NR14R15, —NR14C(═O)R15, —CH2NR14C(═O)R15, —SR14, —S(═O)R15, —SO2R15, or —SO2NR14R15, wherein if R12 is substituted then R12 is substituted with R16; and
each R13 is independently hydrogen, halogen, unsubstituted or substituted C1-C4alkyl, unsubstituted or substituted C1-C4alkoxy, unsubstituted or substituted C1-C4fluoroalkyl, unsubstituted or substituted C1-C4fluoroalkoxy, unsubstituted or substituted monocyclic carbocycle, unsubstituted or substituted monocyclic heterocycle, —CN, —OH, wherein if R13 is substituted then R13 is substituted with R16.

### Claim 10 (depends on 1)

The compound of claim 1, or a pharmaceutically acceptable salt, solvate, diastereomeric mixture, or individual enantiomers thereof, wherein:
each R10 is independently hydrogen, halogen, unsubstituted or substituted C1-C4alkyl, unsubstituted or substituted C1-C4alkoxy, C1-C4fluoroalkyl, C1-C4fluoroalkoxy, unsubstituted or substituted phenyl, unsubstituted or substituted monocyclic heterocycle, —CN, —OH, —CO2R14, —CH2CO2R14, —C(═O)NR14R15, —CH2C(═O)NR14R15, —NR14R15, —CH2NR14R15, —NR14C(═O)R15, or —CH2NR14C(═O)R15, wherein if R10 is substituted then R10 is substituted with 1-4 R16; and
each R11 is independently hydrogen, halogen, unsubstituted or substituted C1-C4alkyl, C1-C4fluoroalkyl, C1-C4alkoxy, C1-C4fluoroalkoxy, or —CN, wherein if R11 is substituted then R11 is substituted with —OR14 or —NR14R15.

### Claim 11 (depends on 1)

The compound of claim 1, or a pharmaceutically acceptable salt, solvate, diastereomeric mixture, or individual enantiomers thereof, wherein:
R4 is hydrogen, or unsubstituted or substituted C1-C6 alkyl, wherein if R4 is substituted then it is substituted with 1-4 R16;
R5 is hydrogen, or unsubstituted or substituted C1-C6 alkyl, wherein if R5 is substituted then it is substituted with 1-4 R16;
R7 is hydrogen;
or R4 and R5 are taken together with the nitrogen atom to which they are attached to form a monocyclic 4- to 7-membered heterocyclic ring, wherein if the heterocyclic ring is substituted then the heterocyclic ring is substituted with 1-4 R16;
or R4 and R7 are taken together with the nitrogen atom to which they are attached to form a monocyclic 4- to 7-membered heterocyclic ring, wherein if the heterocyclic ring is substituted then the heterocyclic ring is substituted with 1-4 R16; and
R9 is hydrogen, unsubstituted or substituted C1-C6 alkyl, or unsubstituted or substituted benzyl, wherein if R9 is substituted then R9 is substituted with 1-4 R16.

### Claim 12 (depends on 1)

The compound of claim 1, or a pharmaceutically acceptable salt, solvate, diastereomeric mixture, or individual enantiomers thereof, wherein:
R4 is hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, sec-butyl, or tert-butyl;
R5 is hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, sec-butyl, or tert-butyl;
R7 is hydrogen;
or R4 and R5 are taken together with the nitrogen atom to which they are attached to form an unsubstituted or substituted monocyclic 4- to 7-membered heterocyclic ring selected from unsubstituted or substituted azetidinyl, unsubstituted or substituted pyrrolidinyl, unsubstituted or substituted pyrrolidinonyl, unsubstituted or substituted piperidinyl, unsubstituted or substituted morpholinyl, unsubstituted or substituted thiomorpholinyl, unsubstituted or substituted piperazinyl, or unsubstituted or substituted azepanyl, wherein if the heterocyclic ring is substituted then the heterocyclic ring is substituted with 1-4 R16;
or R4 and R7 are taken together with the nitrogen atom to which they are attached to form an unsubstituted or substituted monocyclic 4- to 7-membered heterocyclic ring selected from unsubstituted or substituted azetidinyl, unsubstituted or substituted pyrrolidinyl, unsubstituted or substituted pyrrolidinonyl, unsubstituted or substituted piperidinyl, unsubstituted or substituted morpholinyl, unsubstituted or substituted thiomorpholinyl, unsubstituted or substituted piperazinyl, or unsubstituted or substituted azepanyl, wherein if the heterocyclic ring is substituted then the heterocyclic ring is substituted with 1-4 R16; and
R9 is methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, sec-butyl, tert-butyl, or benzyl.

### Claim 13 (depends on 5)

The compound of claim 5, or a pharmaceutically acceptable salt, solvate, diastereomeric mixture, or individual enantiomers thereof,
wherein:

### Claim 14 (depends on 13)

The compound of claim 13, or a pharmaceutically acceptable salt, solvate, diastereomeric mixture, or individual enantiomers thereof,
wherein:
R4 is hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, sec-butyl, or tert-butyl;
R5 is hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, sec-butyl, or tert-butyl;
R7 is hydrogen; and
R9 is methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, sec-butyl, tert-butyl, or benzyl.

### Claim 15 (depends on 5)

The compound of claim 5, or a pharmaceutically acceptable salt, solvate, diastereomeric mixture, or individual enantiomers thereof,
wherein:
p is 1, 2, or 3;
q is 0, 1, or 2; and
R9 is methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, sec-butyl, tert-butyl, or benzyl.

### Claim 16 (depends on 5)

The compound of claim 5, or a pharmaceutically acceptable salt, solvate, diastereomeric mixture, or individual enantiomers thereof, wherein:
p is 1, 2, or 3;
q is 0, 1, or 2; and
R9 is methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, sec-butyl, tert-butyl, or benzyl.

### Claim 17

A compound that is:
1-1: 3-(3-chloro-5-methylphenyl)-6-(3-hydroxyphenyl)-N-methyl-N-[(2S)-pyrrolidin-2-ylmethyl]quinoline-4-carboxamide;
1-2: N-[(2S)-2-aminopropyl]-3-(3-chloro-5-methylphenyl)-6-(3-hydroxyphenyl)-N -methylquinoline-4-carboxamide;
1-3: N-[(2S)-2-aminobutyl]-3-(3-chloro-5-methylphenyl)-6-(3-hydroxyphenyl)-N -methylquinoline-4-carboxamide;
1-4: 3-(3-fluoro-5-methylphenyl)-6-(3-hydroxyphenyl)-N-methyl-N-[(2S)-pyrrolidin-2-ylmethyl]quinoline-4-carboxamide;
1-5: 3-(3-chloro-5-methylphenyl)-6-(3-hydroxyphenyl)-N-methyl-N-[(2R)-pyrrolidin-2-ylmethyl]quinoline-4-carboxamide;
1-6: 3-(3-fluoro-5-methoxyphenyl)-6-(3-hydroxyphenyl)-N-methyl-N-[(2S)-pyrrolidin-2-ylmethyl]quinoline-4-carboxamide;
1-7: N-[(2S)-azetidin-2-ylmethyl]-3-(3-fluoro-5-methylphenyl)-6-(3-hydroxyphenyl)-N -methylquinoline-4-carboxamide;
1-8: N-[(2S)-2-aminobutyl]-6-(3-carbamoyl-5-hydroxyphenyl)-3-(3-chloro-5-methylphenyl)-N -methylquinoline-4-carboxamide;
1-9: N-[(2S)-2-aminobutyl]-6-(3-cyano-5-methoxyphenyl)-3-(3-fluoro-5-methylphenyl)-N -methylquinoline-4-carboxamide;
1-10: N-[(2S)-2-aminobutyl]-6-(3-cyano-5-hydroxyphenyl)-3-(3-fluoro-5-methylphenyl)-N -methylquinoline-4-carboxamide;
1-11: N-[(2S)-2-aminobutyl]-3-(3-fluoro-5-methylphenyl)-6-(5-hydroxy-2-methylphenyl)-N -methylquinoline-4-carboxamide;
1-12: N-[(2S)-2-aminobutyl]-6-(3-cyano-2-methylphenyl)-3-(3-fluoro-5-methylphenyl)-N -methylquinoline-4-carboxamide;
1-13: N-[(2S)-2-aminobutyl]-6-(3-fluoro-2-methylphenyl)-3-(3-fluoro-5-methylphenyl)-N -methylquinoline-4-carboxamide;
1-14: N-[(2S)-2-aminobutyl]-6-(5-cyano-2-methylphenyl)-3-(3-fluoro-5-methylphenyl)-N -methylquinoline-4-carboxamide;
1-15: N-[(2S)-2-aminobutyl]-6-(3-cyano-5-fluorophenyl)-3-(3-fluoro-5-methylphenyl)-N -methylquinoline-4-carboxamide;
1-16: 6-(3-cyanophenyl)-3-(3-fluoro-5-methylphenyl)-N-methyl-N-[(2S)-pyrrolidin-2-ylmethyl]quinoline-4-carboxamide;
1-17: N-[(2S)-2-aminobutyl]-6-(3-fluoro-5-methoxyphenyl)-3-(3-fluoro-5-methylphenyl)-N -methylquinoline-4-carboxamide;
1-18: 3-(3-fluorophenyl)-6-(3-hydroxyphenyl)-N-methyl-N-[(2S)-pyrrolidin-2-ylmethyl]quinoline-4-carboxamide;
1-19: N-[(2S)-2-aminopropyl]-6-(3-cyano-5-methoxyphenyl)-3-(3-fluoro-5-methylphenyl)-N -methylquinoline-4-carboxamide;
1-20: N-[(2S)-2-aminopropyl]-6-(3-cyano-5-fluorophenyl)-3-(3-fluoro-5-methylphenyl)-N -methylquinoline-4-carboxamide;
1-21: 6-(3-cyano-5-methoxyphenyl)-3-(3-fluoro-5-methylphenyl)-N-methyl-N-[(2S) -pyrrolidin-2-ylmethyl]quinoline-4-carboxamide;
1-22: 6-(3-cyano-5-fluorophenyl)-3-(3,5-difluorophenyl)-N-methyl-N-[(2S)-pyrrolidin-2-ylmethyl]quinoline-4-carboxamide;
1-23: 3-(3,5-difluorophenyl)-6-(2-fluoro-3-hydroxyphenyl)-N-methyl-N-[(2S)-pyrrolidin-2-ylmethyl]quinoline-4-carboxamide;
1-24: 6-(3-cyano-5-fluorophenyl)-3-(3-fluoro-5-methylphenyl)-N-methyl-N-[(2S)-pyrrolidin-2-ylmethyl]quinoline-4-carboxamide;
1-25: 6-(3 -cyano-2-fluorophenyl)-3-(3,5-difluorophenyl)-N-methyl-N-[(2S)-pyrrolidin-2-ylmethyl]quinoline-4-carboxamide;
1-26: 6-(3-carbamoyl-5-fluorophenyl)-3-(3,5-difluorophenyl)-N-methyl-N-[(2S)-pyrrolidin-2-ylmethyl]quinoline-4-carboxamide;
1-27: 6-(5-cyano-2-methoxyphenyl)-3-(3,5-difluorophenyl)-N-methyl-N-[(2S)-pyrrolidin-2-ylmethyl]quinoline-4-carboxamide;
1-28: 6-(5-cyano-2-fluorophenyl)-3-(3,5-difluorophenyl)-N-methyl-N-[(2S)-pyrrolidin-2-ylmethyl]quinoline-4-carboxamide;
1-29: 3 -(3-fluoro-5-methylphenyl)-6-(3-hydroxyphenyl)-N-methyl-N-(morpholin-3-ylmethyl)quinoline-4-carboxamide;
1-30: 6-(3-cyano-5-methoxyphenyl)-3-(3,5-difluorophenyl)-N-methyl-N-[(2S)-pyrrolidin-2-ylmethyl]quinoline-4-carboxamide;
1-31: 6-(2-chloro-3-hydroxyphenyl)-3-(3,5-difluorophenyl)-N-methyl-N-[(2S)-pyrrolidin-2-ylmethyl]quinoline-4-carboxamide;
1-32: N-[(2S)-2-aminobutyl]-6-(3-cyano-5-methoxyphenyl)-3-(3,5-difluorophenyl)-N -methylquinoline-4-carboxamide;
1-33: 6-(3-carbamoyl-5-fluorophenyl)-3-(3-fluoro-5-methylphenyl)-N-methyl-N-[(2S) -pyrrolidin-2-ylmethyl]quinoline-4-carboxamide;
1-34: 6-(3-cyano-5-fluorophenyl)-3-(3-fluoro-5-hydroxyphenyl)-N-methyl-N-[(2S)-pyrrolidin -2-ylmethyl]quinoline-4-carboxamide;
1-35: 6-(3-cyano-5-fluorophenyl)-3-[3-fluoro-5-(2-hydroxyethyl)phenyl]-N-methyl-N-[(2S) -pyrrolidin-2-ylmethyl]quinoline-4-carboxamide;
1-36: 3 -fluoro-5-[3-(3-fluoro-5-methylphenyl)-4-{methyl[(2S)-pyrrolidin-2-ylmethyl]carbamoyl}quinolin-6-yl]benzoic acid;
1-37: 4-{3-[6-(3-cyano-5-fluorophenyl)-4-{methyl[(2S)-pyrrolidin-2-ylmethyl]carbamoyl}quinolin-3-yl]-5-fluorophenoxy}butanoic acid;
1-38: N-[(2 S)-2-aminobutyl]-6-(3-cyano-5-hydroxyphenyl)-3-(3,5-difluorophenyl)-N -methylquinoline-4-carboxamide;
1-39: 6-(3-cyano-5-fluorophenyl)-3-[3-fluoro-5-(2-hydroxyethoxy)phenyl]-N-methyl-N-[(2S) -pyrrolidin-2-ylmethyl]quinoline-4-carboxamide;
1-40: 6-[3-cyano-5-(trifluoromethyl)phenyl]-3-(3-fluoro-5-methylphenyl)-N-methyl-N-[(2S) -pyrrolidin-2-ylmethyl]quinoline-4-carboxamide;
1-41: 6-(2-chloro-3-hydroxyphenyl)-3-(3-fluoro-5-methylphenyl)-N-methyl-N-[(2S) -pyrrolidin-2-ylmethyl]quinoline-4-carboxamide;
1-42: 6-(3-cyano-5-fluorophenyl)-3-[3-fluoro-5-(2-methoxyethoxy)phenyl]-N-methyl-N-[(2S) -pyrrolidin-2-ylmethyl]quinoline-4-carboxamide;
1-43: 3 -(3-fluoro-5 -methylphenyl)-6- [3-hydroxy-2-(methoxymethyl)phenyl]-N-methyl-N -[(2S)-pyrrolidin-2-ylmethyl]quinoline-4-carboxamide
1-44: 3-[3-(3-fluoro-5-methylphenyl)-4-{methyl[(2S)-pyrrolidin-2-ylmethyl]carbamoyl}quinolin-6-yl]benzoic acid;
1-45: 6-(3-cyano-2-methylphenyl)-3-[3-fluoro-5-(2-hydroxyethyl)phenyl]-N-methyl-N-[(2S) -pyrrolidin-2-ylmethyl]quinoline-4-carboxamide;
1-46: 4-[3-(3-fluoro-5-methylphenyl)-4-{methyl[(2S)-pyrrolidin-2-ylmethyl]carbamoyl}quinolin-6-yl]benzoic acid;
1-47: 2-[3-(3-fluoro-5-methylphenyl)-4-{methyl[(2S)-pyrrolidin-2-ylmethyl]carbamoyl}quinolin-6-yl]benzoic acid;
1-48: 2-{3-[3-(3-fluoro-5-methylphenyl)-4-{methyl[(2S)-pyrrolidin-2-ylmethyl]carbamoyl}quinolin-6-yl]phenyl}acetic acid;
1-49: methyl 2-{3-[3-(3-fluoro-5-methylphenyl)-4-{methyl[(2S)-pyrrolidin-2-ylmethyl]carbamoyl}quinolin-6-yl]phenyl}acetate;
1-50: 3-{3-[3-(3-fluoro-5-methylphenyl)-4-{methyl[(2 S)-pyrrolidin-2-ylmethyl]carbamoyl}quinolin-6-yl]phenyl}propanoic acid;
1-51: 6-(3-cyano-2-methylphenyl)-3-(3,5-difluorophenyl)-N-methyl-N-[(2S)-pyrrolidin-2-ylmethyl]quinoline-4-carboxamide;
1-52: 6-(5-cyano-2-methylphenyl)-3-(3,5-difluorophenyl)-N-methyl-N-[(2S)-pyrrolidin-2-ylmethyl]quinoline-4-carboxamide;
1-53: 6-(3 -carbamoyl-2-fluorophenyl)-3-(3-fluoro-5-methylphenyl)-N-methyl-N-[(2S) -pyrrolidin-2-ylmethyl]quinoline-4-carboxamide;
1-54: 6-(3-carbamoyl-4-fluorophenyl)-3-(3-fluoro-5-methylphenyl)-N-methyl-N-[(2S) -pyrrolidin-2-ylmethyl]quinoline-4-carboxamide;
1-55: N-[(2S)-2-aminobutyl]-6-(3-cyano-5-fluorophenyl)-3-(3,5-difluorophenyl)-N -methylquinoline-4-carboxamide;
1-56: 6-(3-cyano-5-fluorophenyl)-3-(2,5-difluorophenyl)-N-methyl-N-[(2S)-pyrrolidin-2-ylmethyl]quinoline-4-carboxamide;
1-57: 3-(2-chloro-5-methylphenyl)-6-(3-cyano-5-fluorophenyl)-N-methyl-N-[(2S)-pyrrolidin-2-ylmethyl]quinoline-4-carboxamide;
1-58: 6-(3-cyano-5-fluorophenyl)-3-(5-fluoro-2-methylphenyl)-N-methyl-N-[(2S)-pyrrolidin-2-ylmethyl]quinoline-4-carboxamide;
1-59: 2-{3-fluoro-5-[3-(3-fluoro-5-methylphenyl)-4-{methyl[(2S)-pyrrolidin-2-ylmethyl]carbamoyl}quinolin-6-yl]phenyl}acetic acid;
1-60: 3-(3-fluoro-5-methylphenyl)-N-methyl-N-[(2S)-pyrrolidin-2-ylmethyl]-6-(3-sulfamoylphenyl)quinoline-4-carboxamide;
1-61: 6-(3,5-difluorophenyl)-3-(3-fluoro-5-methylphenyl)-N-methyl-N-[(3S)-pyrrolidin-3-yl]quinoline-4-carboxamide;
1-62: 6-(3,5-difluorophenyl)-3-(3-fluoro-5-methylphenyl)-N-methyl-N-[(2S)-pyrrolidin-2-ylmethyl]quinoline-4-carboxamide;
1-63: 6-(6-carbamoylpyrazin-2-yl)-3-(3-fluoro-5-methylphenyl)-N-methyl-N-[(2S)-pyrrolidin-2-ylmethyl]quinoline-4-carboxamide;
1-64: 6-(2-chloro-5-methoxyphenyl)-3-(3-fluoro-5-methylphenyl)-N-methyl-N-[(2S)-pyrrolidin -2-ylmethyl]quinoline-4-carboxamide;
1-65: 2-{3-chloro-5-[6-(3-cyano-5-fluorophenyl)-4-{methyl[(2S)-pyrrolidin-2-ylmethyl]carbamoyl}quinolin-3-yl]phenoxy}acetic acid;
1-66: 3-(3-fluoro-5-methylphenyl)-6-(3-fluoro-5-sulfamoylphenyl)-N-methyl-N-[(2S) -pyrrolidin-2-ylmethyl]quinoline-4-carboxamide;
1-67: 6-(3-cyano-5-fluorophenyl)-3-(2,3-difluorophenyl)-N-methyl-N- [(2 S)-pyrrolidin-2-ylmethyl]quinoline-4-carboxamide;
1-68: N-[(2S)-2-amino-3-methylbutyl]-6-(3,5-difluorophenyl)-3-(3-fluoro-5-methylphenyl)-N -methylquinoline-4-carboxamide;
1-69: 6-(3-cyano-5-fluorophenyl)-3-[3-fluoro-5-(2-hydroxypropan-2-yl)phenyl]-N-methyl-N -[(2S)-pyrrolidin-2-ylmethyl]quinoline-4-carboxamide;
1-70: N-[(2S)-2-aminobutyl]-6-[3-fluoro-5-(trifluoromethyl)phenyl]-3-(3-fluoro-5-methylphenyl)-N-methylquinoline-4-carboxamide;
1-71: 6-(3-cyano-5-fluorophenyl)-3-[3-fluoro-5-(prop-1-en-2-yl)phenyl]-N-methyl-N-[(2S) -pyrrolidin-2-ylmethyl]quinoline-4-carboxamide;
1-72: 6-(3-carbamoyl-4-hydroxyphenyl)-3-(3-fluoro-5-methylphenyl)-N-methyl-N-[(2S) -pyrrolidin-2-ylmethyl]quinoline-4-carboxamide;
1-73: 3-[3-(dimethylcarbamoyl)phenyl]-6-(3-hydroxyphenyl)-N-methyl-N-[(2S)-pyrrolidin-2-ylmethyl]quinoline-4-carboxamide;
1-74: 6- [3-(carbamoylmethyl)-5-fluorophenyl]-3-(3-fluoro-5-methylphenyl)-N-methyl-N -[(2S)-pyrrolidin-2-ylmethyl]quinoline-4-carboxamide;
1-75: N- [(2 S)-2-aminopropyl]-6-(3-carbamoyl-5-methoxyphenyl)-3-(3-fluoro-5-methylphenyl) -N-methylquinoline-4-carboxamide;
1-76: 3-(4-{[(2S)-2-aminopropyl](methyl)carbamoyl}-3-(3-fluoro-5-methylphenyl)quinolin-6-yl)-5-methoxybenzoic acid;
1-76: 6-[3-cyano-5-(methylcarbamoyl)phenyl]-3-(3-fluoro-5-methylphenyl)-N-methyl-N-[(2S) -pyrrolidin-2-ylmethyl]quinoline-4-carboxamide;
1-77: 6-(3-cyano-2-hydroxyphenyl)-3-(3-fluoro-5-methylphenyl)-N-methyl-N-[(2S)-pyrrolidin -2-ylmethyl]quinoline-4-carboxamide;
1-78: 6-(3-carbamoyl-5-cyanophenyl)-3-(3,5-difluorophenyl)-N-methyl-N-[(2S)-pyrrolidin-2-ylmethyl]quinoline-4-carboxamide;
1-79: 6-(3-cyano-5-fluorophenyl)-3-(3-fluoro-5-methylphenyl)-N-{[(2S,4R)-4-fluoropyrrolidin -2-yl]methyl}-N-methylquinoline-4-carboxamide;
1-80: N-[(2S)-azetidin-2-ylmethyl]-3-(3-chloro-5-methylphenyl)-6-(3-cyano-5-fluorophenyl)-N -methylquinoline-4-carboxamide;
1-81: N-[(2S)-azetidin-2-ylmethyl]-6-(3-carbamoyl-5-fluorophenyl)-3-(3-chloro-5-methylphenyl)-N-methylquinoline-4-carboxamide;
1-82: N-[(2S)-azetidin-2-ylmethyl]-6-(3-cyano-5-fluorophenyl)-3-(3,5-dichlorophenyl)-N -methylquinoline-4-carboxamide;
1-83: N-[(2S)-azetidin-2-ylmethyl]-6-(3-carbamoyl-5-fluorophenyl)-3-(3,5-dichlorophenyl)-N -methylquinoline-4-carboxamide;
1-84: N-[(2S)-azetidin-2-ylmethyl]-3-(3-chloro-5-methylphenyl)-6-(3-cyano-2-hydroxyphenyl) -N-methylquinoline-4-carboxamide;
1-85: N-[(2S)-azetidin-2-ylmethyl]-6-(3-cyano-2-hydroxyphenyl)-3-(3,5-dichlorophenyl)-N -ethylquinoline-4-carboxamide;
1-86: N-[(2S)-azetidin-2-ylmethyl]-3-(3-chloro-5-fluorophenyl)-6-(3-cyano-2-hydroxyphenyl) -N-methylquinoline-4-carboxamide;
1-87: 3-(3-chloro-5-fluorophenyl)-6-(3-cyano-2-hydroxyphenyl)-N-methyl-N-[(2S)-pyrrolidin -2-ylmethyl]quinoline-4-carboxamide;
1-88: 6-(3-carbamoyl-5-methylphenyl)-3-(3-chloro-5-fluorophenyl)-N-methyl-N-[(2S) -pyrrolidin-2-ylmethyl]quinoline-4-carboxamide;
1-89: N-[(2S)-2-amino-4-fluorobutyl]-6-(3,5-difluorophenyl)-3-(3-fluoro-5-methylphenyl)-N -methylquinoline-4-carboxamide;
1-90: 6-(3-cyano-5-fluorophenyl)-3-(3-fluoro-5-methylphenyl)-N- {[(2S,4S)-4-fluoropyrrolidin -2-yl]methyl}-N-methylquinoline-4-carboxamide;
1-91: 6-(3-fluoro-2-hydroxyphenyl)-3-(3-fluoro-5-methylphenyl)-N-methyl-N-[(2S)-pyrrolidin -2-ylmethyl]quinoline-4-carboxamide;
2-1: 3-(3-chloro-5-methylphenyl)-6-(3-hydroxyphenyl)-N-methyl-N-[(2S)-pyrrolidin-2-ylmethyl]-1,5-naphthyridine-4-carboxamide;
2-2: 3,6-bis(3-hydroxyphenyl)-N-methyl-N-[(2S)-pyrrolidin-2-ylmethyl]-1,5-naphthyridine-4-carboxamide;
2-3: 3-(3-chloro-5-methylphenyl)-6-(2-fluoro-5-hydroxyphenyl)-N-methyl-N-[(2S)-pyrrolidin -2-ylmethyl]- 1,5-naphthyridine-4-carboxamide;
2-4: 3-(3-chloro-5-methylphenyl)-6-(3-cyano-5-hydroxyphenyl)-N-methyl-N-[(2S)-pyrrolidin -2-ylmethyl]- 1,5-naphthyridine-4-carboxamide;
2-5: N-[(2S)-2-aminobutyl]-6-(3-cyano-5-hydroxyphenyl)-3-(3,5-dimethylphenyl)-N-methyl -1,5-naphthyridine-4-carboxamide;
2-6: N-[(2S)-2-aminobutyl]-3-(3-chloro-5-methylphenyl)-6-(3-cyano-5-hydroxyphenyl)-N -methyl-1,5-naphthyridine-4-carboxamide;
2-7: N-[(2S)-2-aminobutyl]-6-(3-cyano-5-hydroxyphenyl)-3-(3-fluoro-5-methylphenyl)-N -methyl-1,5-naphthyridine-4-carboxamide;
2-8: 6-(3-hydroxyphenyl)-N-methyl-3-[3-(1H-pyrazol-1-yl)phenyl]-N-[(2S)-pyrrolidin-2-ylmethyl]-1,5-naphthyridine-4-carboxamide;
2-9: 3-(3,5-difluorophenyl)-6-(3-hydroxyphenyl)-N-methyl-N-[(2S)-pyrrolidin-2-ylmethyl]-1,5-naphthyridine-4-carboxamide;
2-10: 6-(3-cyano-5-fluorophenyl)-3-[3-(2-hydroxyethyl)phenyl]-N-methyl-N-[(2S)-pyrrolidin-2-ylmethyl]-1,5-naphthyridine-4-carboxamide;
2-11: 6-(3-cyano-5-fluorophenyl)-N-methyl-3-phenyl-N-[(2S)-pyrrolidin-2-ylmethyl]-1,5-naphthyridine-4-carboxamide;
2-12: 6-(3-cyano-5-fluorophenyl)-3-(3-methoxyphenyl)-N-methyl-N-[(2S)-pyrrolidin-2-ylmethyl]-1,5-naphthyridine-4-carboxamide;
2-13: 6-(3-cyano-5-fluorophenyl)-3-(3-fluorophenyl)-N-methyl-N-[(2S)-pyrrolidin-2-ylmethyl]-1,5-naphthyridine-4-carboxamide;
2-14: 6-(3-cyano-5-fluorophenyl)-3-[3-(acetamidomethyl)phenyl]-N-methyl-N-[(2S)-pyrrolidin -2-ylmethyl]-1,5-naphthyridine-4-carboxamide;
2-15: 6-(3-cyano-5-fluorophenyl)-3-(3-cyanophenyl)-N-methyl-N-[(2S)-pyrrolidin-2-ylmethyl]-1,5-naphthyridine-4-carboxamide;
2-16: 6-(3-cyano-5-fluorophenyl)-3-(3,5-difluorophenyl)-N-methyl-N-[(2S)-pyrrolidin-2-ylmethyl]-1,5-naphthyridine-4-carboxamide;
2-17: 6-(3-cyano-5-fluorophenyl)-3-(3-fluoro-5-methylphenyl)-N-methyl-N-[(2S)-pyrrolidin-2-ylmethyl]-1,5-naphthyridine-4-carboxamide;
2-18: 6-(3-cyano-5-fluorophenyl)-3-(3-fluoro-5-methoxyphenyl)-N-methyl-N-[(2S)-pyrrolidin -2-ylmethyl]- 1,5-naphthyridine-4-carboxamide;
2-19: 6-(3-cyanophenyl)-3-(3,5-difluorophenyl)-N-methyl-N-[(2S)-pyrrolidin-2-ylmethyl]-1,5-naphthyridine-4-carboxamide;
2-20: 2-{3-[6-(3-hydroxyphenyl)-4-[methyl(pyrrolidin-2-ylmethyl)carbamoyl]-1,5-naphthyridin-3-yl]phenyl}acetic acid;
2-21: methyl 2-{3-[6-(3-hydroxyphenyl)-4-{methyl[(2S)-pyrrolidin-2-ylmethyl]carbamoyl}-1,5-naphthyridin-3-yl]phenyl}acetate;
2-22: 3-{3-[6-(3-hydroxyphenyl)-4-{methyl[(2S)-pyrrolidin-2-ylmethyl]carbamoyl}-1,5-naphthyridin-3-yl]phenyl}propanoic acid;
2-23: methyl 3-{3-[6-(3-hydroxyphenyl)-4-{methyl[(2S)-pyrrolidin-2-ylmethyl]carbamoyl}-1,5-naphthyridin-3-yl]phenyl}propanoate;
2-24: 6-(3-carbamoyl-5-fluorophenyl)-3-(3-fluoro-5-methylphenyl)-N-methyl-N-[(2S) -pyrrolidin-2-ylmethyl]-1,5-naphthyridine-4-carboxamide;
3-1: 6-(3-hydroxyphenyl)-N-methyl-N-[(2S)-pyrrolidin-2-ylmethyl]-1,5-naphthyridine-4-carboxamide;
3-2: 3-(3-fluoro-5-methylphenyl)-N-methyl-6-(pyrrolidin-1-yl)-N-[(2S)-pyrrolidin-2-ylmethyl]-1,5-naphthyridine-4-carboxamide;
3-3: 3-(3-fluoro-5-methylphenyl)-6-(3-hydroxypiperidin-1-yl)-N-methyl-N-[(2S)-pyrrolidin-2-ylmethyl]-1,5-naphthyridine-4-carboxamide;
3-4: 6-(3-hydroxyphenyl)-N-methyl-3-(pyrrolidin-1-yl)-N-[(2S)-pyrrolidin-2-ylmethyl]-1,5-naphthyridine-4-carboxamide;
3-5: 6-(3-hydroxyphenyl)-N-methyl-3-(6-methylpyridin-2-yl)-N-[(2S)-pyrrolidin-2-ylmethyl]-1,5-naphthyridine-4-carboxamide;
3-6: 3-(2,6-dimethylmorpholin-4-yl)-6-(3-hydroxyphenyl)-N-methyl-N-[(2 S)-pyrrolidin-2-ylmethyl]-1,5-naphthyridine-4-carboxamide;
3-7: 6-(3-cyano-5-fluorophenyl)-N-methyl-3-(prop-1-yn-1-yl)-N-[(2S)-pyrrolidin-2-ylmethyl]-1,5-naphthyridine-4-carboxamide;
3-8: 6-(5-cyanopyridin-3-yl)-3-(3-fluoro-5-methylphenyl)-N-methyl-N-[(2S)-pyrrolidin-2-ylmethyl]quinoline-4-carboxamide;
3-9: 6-(3-cyano-5-fluorophenyl)-3-(cyclopent-1-en-1-yl)-N-methyl-N-[(2S)-pyrrolidin-2-ylmethyl]-1,5-naphthyridine-4-carboxamide;
3-10: 3-(3-fluoro-5-methylphenyl)-N-methyl-6-(1-methyl-1H-pyrazol-4-yl)-N-[(2S)-pyrrolidin -2-ylmethyl]quinoline-4-carboxamide;
3-11: 6-(3-hydroxyphenyl)-N-methyl-3-(piperidin-1-yl)-N-[(2S)-pyrroldin-2-ylmethyl]-1,5-naphthyridine-4-carboxamide;
3-12: 6-(3-hydroxyphenyl)-N-methyl-3-(morpholin-4-yl)-N-[(2S)-pyrrolidin-2-ylmethyl]-1,5-naphthyridine-4-carboxamide;
3-13: 6-(6-cyanopyridin-2-yl)-3-(3-fluoro-5-methylphenyl)-N-methyl-N-[(2 S)-pyrrolidin-2-ylmethyl]quinoline-4-carboxamide;
3-14: 6-(4-cyanopyridin-2-yl)-3-(3-fluoro-5-methylphenyl)-N-methyl-N-[(2S)-pyrrolidin-2-ylmethyl]quinoline-4-carboxamide;
3-15: 6-(2-amino-5-cyanopyridin-3-yl)-3-(3-fluoro-5-methylphenyl)-N-methyl-N-[(2S) -pyrrolidin-2-ylmethyl]quinoline-4-carboxamide;
3-16: 6-(2-cyanopyridin-4-yl)-3-(3-fluoro-5-methylphenyl)-N-methyl-N-[(2S)-pyrrolidin-2-ylmethyl]quinoline-4-carboxamide;
3-17: 3-[3-(hydroxymethyl)pyrrolidin-1-yl]-6-(3-hydroxyphenyl)-N-methyl-N-[(2S)-pyrrolidin -2-ylmethyl]-1,5-naphthyridine-4-carboxamide;
3-18: 6-(3-hydroxyphenyl)-N-methyl-3-(prop-1-yn-1-yl)-N-((2S)-pyrrolidin-2-ylmethyl)-1,5-naphthyridine-4-carboxamide;
3-19: 6-(4-cyanopyrimidin-2-yl-3-(3-fluoro-5-methylphenyl)-N-methyl-N-[(2S)-pyrrolidin-2-ylmethyl]quinoline-4-carboxamide;
3-20: 3-(cis-2,6-dimethylmorpholin-4-yl)-6-(3-hydroxyphenyl)-N-methyl-N-[(2S)-pyrrolidin-2-ylmethyl]quinoline-4-carboxamide;
3-21: 3-(trans-2,6-dimethylmorpholin-4-yl-6-(3-hydroxyphenyl)-N-methyl-N-[(2S)-pyrrolidin -2-ylmethyl]quinoline-4-carboxamide;
3-22: 6-(5-cyano-2,4-dimethylpyridin-3-yl)-3-(3-fluoro-5-methylphenyl)-N-methyl-N-[(2S) -pyrrolidin-2-ylmethyl]quinoline-4-carboxamide;
3-33: 6-(2-carbamoylpyridin-4-yl)-3-(3-fluoro-5-methylphenyl)-N-methyl-N-[(2S)-pyrrolidin -2-ylmethyl]quinoline-4-carboxamide;
3-34: 6-(3-cyano-5-fluorophenyl)-3-(2-fluoro-3,5-dimethylphenyl)-N-methyl-N-[(2S) -pyrrolidin-2-ylmethyl]quinoline-4-carboxamide;
3-35: 6-(3-cyano-5-fluorophenyl)-3-(2,6-dimethylmorpholin-4-yl)-N-methyl-N-[(2S) -pyrrolidin-2-ylmethyl]-1,5-naphthyridine-4-carboxamide;
3-36: 6-(3-cyano-5-fluorophenyl)-3-(2,6-dimethylmorpholin-4-yl)-N-methyl-N-[(2S) -pyrrolidin-2-ylmethyl]-1,5-naphthyridine-4-carboxamide;
3-37: 6-[5-cyano-2-(methylamino)pyridin-3-yl]-3-(3-fluoro-5-methylphenyl)-N-methyl-N -[(2S)-pyrrolidin-2-ylmethyl]quinoline-4-carboxamide;
3-38: 6-[5-cyano-2-(dimethylamino)pyridin-3-yl]-3-(3-fluoro-5-methylphenyl)-N-methyl-N -[(2S)-pyrrolidin-2-ylmethyl]quinoline-4-carboxamide;
3-39: 6-(5-cyano-2-methylpyridin-3-yl)-3-(3-fluoro-5-methylphenyl)-N-methyl-N-[(2S) -pyrrolidin-2-ylmethyl]quinoline-4-carboxamide;
3-40: 6-(5-cyanopyridin-3-yl)-3-[3-fluoro-5-(2-hydroxyethyl)phenyl]-N-methyl-N-[(2S) -pyrrolidin-2-ylmethyl]quinoline-4-carboxamide;
3-41: N-[(2S)-2-aminobutyl]-6-[5-cyano-2-(dimethylamino)pyridin-3-yl]-3-(3-fluoro-5-methylphenyl)-N-methylquinoline-4-carboxamide;
3-42: 6-(3-cyano-5-fluorophenyl)-N-methyl-3-[(2R)-2-phenylmorpholin-4-yl]-N-[(2S) -pyrrolidin-2-ylmethyl]-1,5-naphthyridine-4-carboxamide;
3-43: 6-(3-cyano-5-fluorophenyl)-N-methyl-3-(3-methylbutyl)-N-[(2S)-pyrrolidin-2-ylmethyl]-1,5-naphthyridine-4-carboxamide;
3-44: 6-(6-carbamoylpyrazin-2-yl)-3-(3-fluoro-5-methylphenyl)-N-methyl-N-[(2S)-pyrrolidin-2-ylmethyl]quinoline-4-carboxamide;
3-45: 6-(3-cyano-5-fluorophenyl)-3-(2,6-dimethylmorpholin-4-yl)-N-methyl-N-[(2S) -pyrrolidin-2-ylmethyl]quinoline-4-carboxamide;
3-46: 3-(3-fluoro-5-methylphenyl)-N-methyl-6-[6-(methylcarbamoyl)pyridin-2-yl]-N-[(2S) -pyrrolidin-2-ylmethyl]quinoline-4-carboxamide;
3-47: 6-(3-cyano-5-fluorophenyl)-N-methyl-3-[(2S)-2-phenylmorpholin-4-yl]-N-[(2S) -pyrrolidin-2-ylmethyl]-1,5-naphthyridine-4-carboxamide;
3-48: 3-(3-fluoro-5-methylphenyl)-N-methyl-6-(pyridin-3-yl)-N-[(2S)-pyrrolidin-2-ylmethyl]quinoline-4-carboxamide;
3-49: 6-(3-cyano-5-fluorophenyl)-N-methyl-N-[(2S)-pyrrolidin-2-ylmethyl]-3-(2,2,6,6-tetramethylmorpholin-4-yl)-1,5-naphthyridine-4-carboxamide;
3-50: 6-(3-carbamoyl-4,5-difluorophenyl)-3-(3-fluoro-5-methylphenyl)-N-methyl-N-[(2S) -pyrrolidin-2-ylmethyl]quinoline-4-carboxamide;
3-51: 6-(6-aminopyridin-2-yl)-3-(3-fluoro-5-methylphenyl)-N-methyl-N-[(2S)-pyrrolidin-2-ylmethyl]quinoline-4-carboxamide;
3-52: 6-(3-carbamoyl-2,5-difluorophenyl)-3-(3-fluoro-5-methylphenyl)-N-methyl-N-[(2S) -pyrrolidin-2-ylmethyl]quinoline-4-carboxamide;
3-53: 3-(3-fluoro-5-methylphenyl)-6-(6-methoxypyridin-2-yl)-N-methyl-N-[(2S)-pyrrolidin-2-ylmethyl]quinoline-4-carboxamide;
3-54: 6-(3-cyano-5-fluorophenyl)-N-methyl-N-[(2S)-pyrrolidin-2-ylmethyl]-3-[5-(trifluoromethyl)-2,3-dihydro-1H-indol-1-yl]-1,5-naphthyridine-4-carboxamide;
3-55: 6-(3-cyano-5-fluorophenyl)-N-methyl-N-[(2S)-pyrrolidin-2-ylmethyl]-3-[5-(trifluoromethyl)-2,3-dihydro-1H-isoindol-2-yl]-1,5-naphthyridine-4-carboxamide;
3-56: 6-(5-cyano-2-hydroxypyridin-3-yl)-3-(3-fluoro-5-methylphenyl)-N-methyl-N-[(2S) -pyrrolidin-2-ylmethyl]quinoline-4-carboxamide;
3-57: 6-(6-carbamoyl-3-methylpyridin-2-yl)-3-(3-fluoro-5-methylphenyl)-N-methyl-N-[(2S) -pyrrolidin-2-ylmethyl]quinoline-4-carboxamide;
3-58: 6-(5-carbamoylpyridin-3-yl)-3-[3-fluoro-5-(2-hydroxyethyl)phenyl]-N-methyl-N-[(2S) -pyrrolidin-2-ylmethyl]quinoline-4-carboxamide;
3-59: 3-(3-fluoro-5-methylphenyl)-6-(5-fluoropyridin-3-yl)-N-methyl-N-[(2S)-pyrrolidin-2-ylmethyl]quinoline-4-carboxamide;
3-60: 3-(3-fluoro-5-methylphenyl)-6-(1H-indo1-6-yl)-N-methyl-N-[(2S)-pyrrolidin-2-ylmethyl]quinoline-4-carboxamide;
3-61: 3-(3-fluoro-5-methylphenyl)-6-(1H-indol-4-yl)-N-methyl-N-[(2S)-pyrrolidin-2-ylmethyl]quinoline-4-carboxamide;
3-62: 6-(2-amino-5-fluoropyridin-3-yl)-3-(3-fluoro-5-methylphenyl)-N-methyl-N-[(2S) -pyrrolidin-2-ylmethyl]quinoline-4-carboxamide;
3-64: 6-(3-carbamoyl-5-fluorophenyl)-3-[(cis)-2,6-dimethylmorpholin-4-yl]-N-methyl-N-[(2S) -pyrrolidin-2-ylmethyl]quinoline-4-carboxamide;
3-65: 3-(3-fluoro-5-methylphenyl)-N-methyl-6-(4-methylpyridin-3-yl)-N-[(2S)-pyrrolidin-2-ylmethyl]quinoline-4-carboxamide;
3-66: 3-(3-fluoro-5-methylphenyl)-N-methyl-6-(1-oxo-2,3-dihydro-1H-isoindol-4-yl)-N-[(2S) -pyrrolidin-2-ylmethyl]quinoline-4-carboxamide;
3-67: N-[(2S)-2-aminobutyl]-6-(6-carbamoylpyridin-2-yl)-3-(3-fluoro-5-methylphenyl)-N -methylquinoline-4-carboxamide;
3-68: 6-(5-chloropyridin-3-yl)-3-(3-fluoro-5-methylphenyl)-N-methyl-N-[(2S)-pyrrolidin-2-ylmethyl]quinoline-4-carboxamide;
3-69: 3-{3-azabicyclo[3.1.0]hexan-3-yl}-6-(3-cyano-5-fluorophenyl)-N-methyl-N-[(2S) -pyrrolidin-2-ylmethyl]-1,5-naphthyridine-4-carboxamide;
3-70: 6-(3-cyano-5-fluorophenyl)-N-methyl-3-{8-oxa-3-azabicyclo[3.2.1]octan-3-yl}-N-[(2S) -pyrrolidin-2-ylmethyl]-1,5-naphthyridine-4-carboxamide;
3-71: 3-(3-fluoro-5-methylphenyl)-N-methyl-6-(pyrimidin-5-yl)-N-[(2S)-pyrrolidin-2-ylmethyl]quinoline-4-carboxamide;
3-72: 6-[4-cyano-6-(morpholin-4-yl)pyridin-2-yl]-3-(3-fluoro-5-methylphenyl)-N-methyl-N -[(2S)-pyrrolidin-2-ylmethyl]quinoline-4-carboxamide;
3-73: 3-(3-fluoro-5-methylphenyl)-N-methyl-6-[2-oxo-6-(trifluoromethyl)-2,3-dihydro-1H -1,3-benzodiazol-4-yl]-N-[(2S)-pyrrolidin-2-ylmethyl]quinoline-4-carboxamide;
3-74: 3-(3-fluoro-5-methylphenyl)-6-(4-fluoropyridin-3-yl)-N-methyl-N-[(2S)-pyrrolidin-2-ylmethyl]quinoline-4-carboxamide;
3-75: 6-(4-chloropyridin-3-yl)-3-(3-fluoro-5-methylphenyl)-N-methyl-N-[(2S)-pyrrolidin-2-ylmethyl]quinoline-4-carboxamide;
3-76: 6-(3-cyano-5-fluorophenyl)-3-(3,3-difluoropyrrolidin-1-yl)-N-methyl-N-[(2S)-pyrrolidin -2-ylmethyl]-1,5-naphthyridine-4-carboxamide;
3-77: 6-(6-carbamoylpyridin-2-yl)-3-(3,5-difluorophenyl)-N-methyl-N-[(2S)-pyrrolidin-2-ylmethyl]quinoline-4-carboxamide;
3-78: 6-(6-carbamoyl-3-fluoropyridin-2-yl)-3-(3-fluoro-5-methylphenyl)-N-methyl-N-[(2S) -pyrrolidin-2-ylmethyl]quinoline-4-carboxamide;
3-79: 6-(6-carbamoyl-3-methylpyridin-2-yl)-3-(3,5-difluorophenyl)-N-methyl-N-[(2S) -pyrrolidin-2-ylmethyl]quinoline-4-carboxamide;
3-80: 6-(4-carbamoylpyridin-2-yl)-3-(3-fluoro-5-methylphenyl)-N-methyl-N-[(2S)-pyrrolidin -2-ylmethyl]quinoline-4-carboxamide;
3-81: 3-(3-fluoro-5-methylphenyl)-6-(5-methoxypyridin-3-yl)-N-methyl-N-[(2S)-pyrrolidin-2-ylmethyl]quinoline-4-carboxamide;
3-82: 3-(3-fluoro-5-methylphenyl)-N-methyl-N-[(2S)-pyrrolidin-2-ylmethyl]-6-(6-sulfamoylpyridin-2-yl)quinoline-4-carboxamide;
3-83: 3-(3-fluoro-5-methylphenyl)-N-methyl-6-(5-methylpyridin-3-yl)-N-[(2S)-pyrrolidin-2-ylmethyl]quinoline-4-carboxamide;
3-84: 3-(3-fluoro-5-methylphenyl)-6-[5-(hydroxymethyl)pyridin-3-yl]-N-methyl-N-[(2S) -pyrrolidin-2-ylmethyl]quinoline-4-carboxamide;
3-85: 3-(3-chloro-5-methylphenyl)-6-(5-hydroxypyridin-3-yl)-N,7-dimethyl-N-[(2S)-pyrrolidin -2-ylmethyl]-3,4-dihydroquinazoline-4-carboxamide;
3-86: 6-[5-(difluoromethoxy)pyridin-3-yl]-3-(3-fluoro-5-methylphenyl)-N-methyl-N-[(2S) -pyrrolidin-2-ylmethyl]quinoline-4-carboxamide;
3-87: ethyl (2S)-2({1-[6-(6-carbamoylpyridin-2-yl)-3-(3-fluoro-5-methylphenyl)quinolin-4-yl]-N-methylformamido}methyl)pyrrolidine-1-carboxylate;
3-88: 6-(6-carbamoylpyridin-2-yl)-3-(3-chloro-5-methylphenyl)-N-methyl-N-[(2S)-pyrrolidin-2-ylmethyl]quinoline-4-carboxamide;
3-89: 6-(6-carbamoyl-3-fluoropyridin-2-yl)-3-(3-chloro-5-methylphenyl)-N-methyl-N-[(2S) -pyrrolidin-2-ylmethyl]quinoline-4-carboxamide;
3-90: 6-(6-carbamoyl-3-methylpyridin-2-yl)-3-(3-chloro-5-methylphenyl)-N-methyl-N-[(2S) -pyrrolidin-2-ylmethyl]quinoline-4-carboxamide;
3-91: 6-(6-carbamoyl-3-chloropyridin-2-yl)-3-(3-chloro-5-methylphenyl)-N-methyl-N-[(2S) -pyrrolidin-2-ylmethyl]quinoline-4-carboxamide;
3-92: N-[(2S)-azetidin-2-ylmethyl]-6-(6-carbamoylpyridin-2-yl)-3-(3-fluoro-5-methylphenyl) -N-methylquinoline-4-carboxamide;
3-93: N-[(2S)-azetidin-2-ylmethyl]-6-(6-carbamoyl-3-fluoropyridin-2-yl)-3-(3-fluoro-5-methylphenyl)-N-methylquinoline-4-carboxamide;
3-94: N-[(2S)-azetidin-2-ylmethyl]-6-(6-carbamoyl-3-methylpyridin-2-yl)-3-(3-fluoro-5-methylphenyl)-N-methylquinoline-4-carboxamide;
3-95: N-[(2S)-azetidin-2-ylmethyl]-6-(6-carbamoyl-3-chloropyridin-2-yl)-3-(3-fluoro-5-methylphenyl)-N-methylquinoline-4-carboxamide;
3-96: 6-(6-carbamoylpyridin-2-yl)-3-(3,5-dichlorophenyl)-N-methyl-N-[(2S)-pyrrolidin-2-ylmethyl]quinoline-4-carboxamide;
3-97: 6-(6-carbamoyl-3-fluoropyridin-2-yl)-3-(3,5-dichlorophenyl)-N-methyl-N-[(2S) -pyrrolidin-2-ylmethyl]quinoline-4-carboxamide;
3-98: 6-(6-carbamoyl-3-methylpyridin-2-yl)-3-(3,5-dichlorophenyl)-N-methyl-N-[(2S) -pyrrolidin-2-ylmethyl]quinoline-4-carboxamide;
3-99: 6-(6-carbamoyl-3-chloropyridin-2-yl)-3-(3,5-dichlorophenyl)-N-methyl-N-[(2S) -pyrrolidin-2-ylmethyl]quinoline-4-carboxamide;
3-100: N-[(2S)-azetidin-2-ylmethyl]-6-(6-carbamoylpyridin-2-yl)-3-(3,5-dichlorophenyl)-N -methylquinoline-4-carboxamide;
3-101: N-[(2S)-azetidin-2-ylmethyl]-6-(6-carbamoyl-3-fluoropyridin-2-yl)-3-(3,5-dichlorophenyl)-N-methylquinoline-4-carboxamide;
3-102: N-[(2S)-azetidin-2-ylmethyl]-6-(6-carbamoyl-3-methylpyridin-2-yl)-3-(3,5-dichlorophenyl)-N-methylquinoline-4-carboxamide;
3-103: N-[(2S)-azetidin-2-ylmethyl]-6-(6-carbamoyl-3-chloropyridin-2-yl)-3-(3,5-dichlorophenyl)-N-methylquinoline-4-carboxamide;
3-104: 6-(6-carbamoylpyridin-2-yl)-3-(3-fluoro-5-methylphenyl)-N-methyl-N-{[(2S)-1-methylpyrrolidin-2-yl]methyl}quinoline-4-carboxamide;
3-105: 3-(3-fluoro-5-methylphenyl)-N-methyl-N-[(2S)-pyrrolidin-2-ylmethyl]-6-[5-(trifluoromethyl)pyridin-3-yl]quinoline-4-carboxamide;
3-106: 3-(3-fluoro-5-methylphenyl)-N-methyl-6-(4-oxo-3,4-dihydro-2H-1,3-benzoxazin-6-yl) -N-[(2S)-pyrrolidin-2-ylmethyl]quinoline-4-carboxamide;
3-107: 6-(3,5-difluoro-2-hydroxyphenyl)-3-(3-fluoro-5-methylphenyl)-N-methyl-N-[(2S) -pyrrolidin-2-ylmethyl]quinoline-4-carboxamide.
or a pharmaceutically acceptable salt, pharmaceutically acceptable solvate, diastereomeric mixture, or individual enantiomers thereof.

### Claim 18 (depends on 1)

A pharmaceutical composition comprising a compound of claim 1, or a pharmaceutically acceptable salt, solvate, diastereomeric mixture, or individual enantiomers thereof, and at least one pharmaceutically acceptable excipient.

### Claim 19 (depends on 1)

A method of treating a disease or condition in a mammal that would benefit from the modulation of the somatostatin receptor subtype 2 (SSTR2) activity comprising administering a compound of claim 1, or a pharmaceutically acceptable salt, pharmaceutically acceptable solvate, diastereomeric mixture, or individual enantiomers thereof, to the mammal in need thereof; wherein the disease or condition is acromegaly, a neuroendocrine tumor, or combinations thereof.