US 12,441,702 B2
Substituted 4-benzyl and 4-benzoyl piperidine derivates
Nadine C. Becknell, Coatesville, PA (US); Reddeppa Reddy Dandu, Downingtown, PA (US); Bruce D. Dorsey, Ambler, PA (US); Dimitar B. Gotchev, Hatboro, PA (US); Robert L. Hudkins, Chester Springs, PA (US); Linda Weinberg, King of Prussia, PA (US); and Craig A. Zificsak, Downingtown, PA (US)
Assigned to Cephalon LLC, West Chester, PA (US)
Filed by Cephalon LLC, West Chester, PA (US)
Filed on Dec. 1, 2023, as Appl. No. 18/526,380.
Application 18/526,380 is a division of application No. 17/175,751, filed on Feb. 12, 2021, granted, now 11,878,966.
Application 17/175,751 is a continuation of application No. 15/735,811, granted, now 10,919,875, issued on Feb. 16, 2021, previously published as PCT/US2016/037980, filed on Jun. 17, 2016.
Claims priority of provisional application 62/181,391, filed on Jun. 18, 2015.
Prior Publication US 2024/0166625 A1, May 23, 2024
This patent is subject to a terminal disclaimer.
Int. Cl. C07D 401/10 (2006.01); C07D 405/10 (2006.01); C07D 405/14 (2006.01); C07D 413/14 (2006.01); C07D 471/04 (2006.01)
CPC C07D 401/10 (2013.01) [C07D 405/10 (2013.01); C07D 405/14 (2013.01); C07D 413/14 (2013.01); C07D 471/04 (2013.01)] 6 Claims
 
1. A method of treating a subject suffering from a disorder mediated by fatty acid synthase and in need of treatment thereof, wherein the disorder mediated by fatty acid synthase is obesity, an eating disorder, drug induced body weight gain, a cardiovascular disease, a gastrointestinal disorder, a dermatological disorder, a metabolic disease, a viral disorder wherein FASN inhibition correlates inhibition of viral replication, breast cancer, ovarian cancer, prostate cancer, colon cancer, lung cancer, bladder cancer, stomach cancer, kidney cancer, or a cancer metastasis, wherein the method comprises administering to the subject a therapeutically effective amount of a compound, or a pharmaceutically acceptable salt thereof, wherein said compound is
1-[4-(4-quinolin-3-yl-benzyl)-piperidin-1-yl]-propan-1-one;
2-methyl-1-[4-(4-quinolin-3-yl-benzyl)-piperidin-1-yl]-propan-1-one;
cyclopropyl-[4-(4-quinolin-3-yl-benzyl)-piperidin-1-yl]-methanone;
4-(4-quinolin-3-yl-benzyl)-piperidin-1-yl]-(R)-tetrahydrofuran-2-yl-methanone;
4-(4-quinolin-3-yl-benzyl)-piperidin-1-yl]-(S)-tetrahydrofuran-2-yl-methanone;
1-{4-[4-(4-methylquinolin-3-yl)-benzyl]-piperidin-1-yl}-propan-1-one;
cyclopropyl-{4-[4-(4-methylquinolin-3-yl)-benzyl]-piperidin-1-yl}-methanone;
(3,3-difluorocyclobutyl)-{4-[4-(4-methylquinolin-3-yl)-benzyl]-piperidin-1-yl}-methanone;
{4-[4-(4-methylquinolin-3-yl)-benzyl]-piperidin-1-yl}-(R)-tetrahydrofuran-2-yl-methanone;
1-{4-[4-(4-chloroquinolin-3-yl)-benzyl]-piperidin-1-yl}-propan-1-one;
{4-[4-(4-chloroquinolin-3-yl)-benzyl]-piperidin-1-yl}-cyclopropylmethanone;
{4-[4-(4-chloroquinolin-3-yl)-benzyl]-piperidin-1-yl}-(3,3-difluorocyclobutyl)-methanone;
{4-[4-(4-chloroquinolin-3-yl)-benzyl]-piperidin-1-yl}-(R)-tetrahydrofuran-2-yl-methanone;
1-{4-[4-(8-methylquinolin-7-yl)-benzyl]-piperidin-1-yl}-propan-1-one;
cyclopropyl-{4-[4-(8-methylquinolin-7-yl)-benzyl]-piperidin-1-yl}-methanone;
{4-[4-(8-methylquinolin-7-yl)-benzyl]-piperidin-1-yl}-(R)-tetrahydrofuran-2-yl-methanone;
1-{4-[4-(8-chloroquinolin-7-yl)-benzyl]-piperidin-1-yl}-propan-1-one;
{4-[4-(8-chloroquinolin-7-yl)-benzyl]-piperidin-1-yl}-cyclopropylmethanone;
{4-[4-(8-chloroquinolin-7-yl)-benzyl]-piperidin-1-yl}-(R)-tetrahydrofuran-2-yl-methanone;
1-{4-[4-(8-methoxyquinolin-7-yl)-benzyl]-piperidin-1-yl}-propan-1-one;
cyclopropyl-{4-[4-(8-methoxyquinolin-7-yl)-benzyl]-piperidin-1-yl}-methanone;
{4-[4-(8-methoxyquinolin-7-yl)-benzyl]-piperidin-1-yl}-(R)-tetrahydrofuran-2-yl-methanone;
1-{4-[4-(1-methylisoquinolin-6-yl)-benzyl]-piperidin-1-yl}-propan-1-one;
cyclopropyl-{4-[4-(1-methylisoquinolin-6-yl)-benzyl]-piperidin-1-yl}-methanone;
{4-[4-(1-methylisoquinolin-6-yl)-benzyl]-piperidin-1-yl}-(R)-tetrahydrofuran-2-yl-methanone;
1-(4-(1-(4-(quinolin-3-yl) phenyl) ethyl) piperidin-1-yl) propan-1-one;
1-{4-[1-(4-quinolin-3-yl-phenyl)-cyclopropyl]-piperidin-1-yl}-propan-1-one;
1-{4-[1-(4-quinolin-7-yl-phenyl)-ethyl]-piperidin-1-yl}-propan-1-one;
cyclopropyl-{4-[1-(4-quinolin-3-yl-phenyl)-cyclopropyl]-piperidin-1-yl}-methanone;
cyclopropyl-{4-[1-(4-quinolin-7-yl-phenyl)-cyclopropyl]-piperidin-1-yl}-methanone
1-{4-[1-(4-quinolin-3-yl-phenyl)-propyl]-piperidin-1-yl}-propan-1-one;
1-{4-[cyclopropyl-(4-quinolin-3-yl-phenyl)-methyl]-piperidin-1-yl}-propan-1-one;
{4-[1-(4-quinolin-7-yl-phenyl)-ethyl]-piperidin-1-yl}-(R)-tetrahydrofuran-2-yl-methanone;
{4-[1-(4-quinolin-3-yl-phenyl)-ethyl]-piperidin-1-yl}-(R)-tetrahydrofuran-2-yl-methanone;
1-{4-[1-(4-quinolin-3-yl-phenyl)-butyl]-piperidin-1-yl}-propan-1-one;
cyclopropyl-{4-[1-(4-quinolin-3-yl-phenyl)-ethyl]-piperidin-1-yl}-methanone;
1-{4-[2-methyl-1-(4-quinolin-3-yl-phenyl)-propyl]-piperidin-1-yl}-propan-1-one;
1-(4-{1-[4-(8-methylquinolin-7-yl)-phenyl]-ethyl}-piperidin-1-yl)-propan-1-one;
cyclopropyl-(4-{1-[4-(8-methylquinolin-7-yl)-phenyl]-ethyl}-piperidin-1-yl)-methanone;
1-(4-{1-[4-(8-methoxyquinolin-7-yl)-phenyl]-ethyl}-piperidin-1-yl)-propan-1-one;
1-(4-{1-[4-(4-methylquinolin-3-yl)-phenyl]-ethyl}-piperidin-1-yl)-propan-1-one;
cyclopropyl-(4-{1-[4-(8-methoxyquinolin-7-yl)-phenyl]-ethyl}-piperidin-1-yl)-methanone;
1-{4-[1-(4-quinolin-3-yl-phenyl)-ethyl]-piperidin-1-yl}-propan-1-one;
(4-{1-[4-(8-methoxyquinolin-7-yl)-phenyl]-ethyl}-piperidin-1-yl)-(R)-tetrahydrofuran-2-yl-methanone; mixture of diastereomers;
(4-{1-[4-(8-methylquinolin-7-yl)-phenyl]-ethyl}-piperidin-1-yl)-(R)-tetrahydrofuran-2-yl-methanone; mixture of diastereomers;
(4-{1-[4-(4-methylquinolin-3-yl)-phenyl]-ethyl}-piperidin-1-yl)-(R)-tetrahydrofuran-2-yl-methanone; mixture of diastereomers;
1-(4-{1-[4-(8-chloroquinolin-7-yl)-phenyl]-ethyl}-piperidin-1-yl)-propan-1-one;
(4-{1-[4-(8-chloroquinolin-7-yl)-phenyl]-ethyl}-piperidin-1-yl)-cyclopropylmethanone;
(4-{1-[4-(8-chloroquinolin-7-yl)-phenyl]-ethyl}-piperidin-1-yl)-(R)-tetrahydrofuran-2-yl-methanone; mixture of diastereomers;
1-(4-{1-[4-(4-chloroquinolin-3-yl)-phenyl]-ethyl}-piperidin-1-yl)-propan-1-one;
(4-{1-[4-(4-chloroquinolin-3-yl)-phenyl]-ethyl}-piperidin-1-yl)-cyclopropylmethanone;
(4-{1-[4-(4-chloroquinolin-3-yl)-phenyl]-ethyl}-piperidin-1-yl)-(R)-tetrahydrofuran-2-yl-methanone; mixture of diastereomers;
(4-{1-[4-(1-methylisoquinolin-6-yl)-phenyl]-cyclopropyl}-piperidin-1-yl)-(R)-tetrahydrofuran-2-yl-methanone;
(4-{1-[4-(8-methylquinolin-7-yl)-phenyl]-cyclopropyl}-piperidin-1-yl)-(R)-tetrahydrofuran-2-yl-methanone;
1-(4-fluoro-4-(4-(quinolin-3-yl) benzyl) piperidin-1-yl) propan-1-one;
1-(4-fluoro-4-(4-(quinolin-7-yl) benzyl) piperidin-1-yl) propan-1-one;
1-(4-fluoro-4-(4-(isoquinolin-6-yl) benzyl) piperidin-1-yl) propan-1-one;
cyclopropyl(4-fluoro-4-(4-(quinolin-3-yl) benzyl) piperidin-1-yl) methanone;
cyclopropyl(4-fluoro-4-(4-(quinolin-7-yl) benzyl) piperidin-1-yl) methanone;
cyclopropyl(4-fluoro-4-(4-(isoquinolin-6-yl) benzyl) piperidin-1-yl) methanone;
(R)-(4-fluoro-4-(4-(4-methylquinolin-3-yl) benzyl) piperidin-1-yl) (tetrahydrofuran-2-yl) methanone;
cyclopropyl(4-fluoro-4-(4-(8-methylquinolin-7-yl) benzyl) piperidin-1-yl) methanone;
1-(4-fluoro-4-(4-(8-methylquinolin-7-yl) benzyl) piperidin-1-yl) propan-1-one;
(R)-(4-fluoro-4-(4-(quinolin-7-yl) benzyl) piperidin-1-yl) (tetrahydrofuran-2-yl) methanone;
(R)-(4-fluoro-4-(4-(quinolin-3-yl) benzyl) piperidin-1-yl) (tetrahydrofuran-2-yl) methanone;
cyclopropyl(4-fluoro-4-(4-(4-methylquinolin-3-yl) benzyl) piperidin-1-yl) methanone;
1-(4-(4-(4-chloroquinolin-3-yl) benzyl)-4-fluoropiperidin-1-yl) propan-1-one;
1-(4-fluoro-4-(4-(4-methylquinolin-3-yl) benzyl) piperidin-1-yl) propan-1-one;
(4-(4-(4-chloroquinolin-3-yl) benzyl)-4-fluoropiperidin-1-yl) (cyclopropyl) methanone;
(R)-(4-fluoro-4-(4-(8-methylquinolin-7-yl) benzyl) piperidin-1-yl) (tetrahydrofuran-2-yl) methanone;
(R)-(4-(4-(4-chloroquinolin-3-yl) benzyl)-4-fluoropiperidin-1-yl) (tetrahydrofuran-2-yl) methanone;
cyclopropyl(4-(2-(4-(quinolin-3-yl) phenyl) propan-2-yl) piperidin-1-yl) methanone;
1-(4-(2-(4-(quinolin-3-yl) phenyl) propan-2-yl) piperidin-1-yl) propan-1-one;
1-[trans-3-hydroxy-4-(4-quinolin-3-yl-benzyl)-piperidin-1-yl]-propan-1-one;
1-[(trans)-3-methoxy-4-(4-quinolin-3-yl-benzyl)-piperidin-1-yl]-propan-1-one;
1-propionyl-4-(4-quinolin-3-yl-benzyl)-piperidin-3-one;
1-[cis-3-fluoro-4-(4-quinolin-3-yl-benzyl)-piperidin-1-yl]-propan-1-one;
[trans-3-hydroxy-4-(4-quinolin-3-yl-benzyl)-piperidin-1-yl]-(R)-tetrahydrofuran-2-yl-methanone;
N-ethyl-4-fluoro-4-[[4-(8-methyl-7-quinolyl) phenyl]methyl]piperidine-1-carboxamide;
N-ethyl-4-[[4-(8-methyl-7-quinolyl) phenyl]methyl]piperidine-1-carboxamide;
N-ethyl-4-[[4-(8-methoxy-7-quinolyl) phenyl]methyl]piperidine-1-carboxamide;
N-methoxy-4-[[4-(8-methyl-7-quinolyl) phenyl]methyl]piperidine-1-carboxamide;
N-ethoxy-4-[[4-(8-methyl-7-quinolyl) phenyl]methyl]piperidine-1-carboxamide;
N,N-dimethyl-4-[[4-(8-methyl-7-quinolyl) phenyl]methyl]piperidine-1-carboxamide;
[4-[4-(8-methyl-7-quinolyl) phenyl]methyl]-1-piperidyl]-pyrrolidin-1-yl-methanone;
1-[4-(4-quinolin-3-yl-benzyl)-piperidin-1-yl]-propan-1-one;
4-(4-quinolin-3-yl-benzyl)-piperidin-1-yl]-(R)-tetrahydro-furan-2-yl-methanone;
4-(4-quinolin-3-yl-benzyl)-piperidin-1-yl]-(S)-tetrahydro-furan-2-yl-methanone;
1-{4-[fluoro-(4-quinolin-3-yl-phenyl)-methyl]-piperidin-1-yl}-propan-1-one;
cyclopropyl-{4-[fluoro-(4-quinolin-3-yl-phenyl)-methyl]-piperidin-1-yl}-methanone;
{4-[fluoro-(4-quinolin-3-yl-phenyl)-methyl]-piperidin-1-yl}-(R)-tetrahydrofuran-2-yl-methanone;
1-(4-{difluoro-[4-(4-methyl-quinolin-3-yl)-phenyl]-methyl}-piperidin-1-yl)-propan-1-one;
cyclopropyl-(4-{difluoro-[4-(4-methyl-quinolin-3-yl)-phenyl]-methyl}-piperidin-1-yl)-methanone;
(4-{difluoro-[4-(4-methyl-quinolin-3-yl)-phenyl]-methyl}-piperidin-1-yl)-(R)-tetrahydrofuran-2-yl-methanone;
1-{4-[4-(4-methyl-quinolin-3-yl)-benzyl]-piperidin-1-yl}-propan-1-one;
cyclopropyl-{4-[4-(4-methyl-quinolin-3-yl)-benzyl]-piperidin-1-yl}-methanone;
(3,3-difluoro-cyclobutyl)-{4-[4-(4-methyl-quinolin-3-yl)-benzyl]-piperidin-1-yl}-methanone;
{4-[4-(4-methyl-quinolin-3-yl)-benzyl]-piperidin-1-yl}-(R)-tetrahydro-furan-2-yl-methanone;
1-{4-[difluoro-(4-quinolin-3-yl-phenyl)-methyl]-piperidin-1-yl}-propan-1-one;
cyclopropyl-{4-[difluoro-(4-quinolin-3-yl-phenyl)-methyl]-piperidin-1-yl}-methanone;
{4-[difluoro-(4-quinolin-3-yl-phenyl)-methyl]-piperidin-1-yl}-(R)-tetrahydrofuran-2-yl-methanone;
1-{4-[4-(4-chloro-quinolin-3-yl)-benzyl]-piperidin-1-yl}-propan-1-one;
{4-[4-(4-chloro-quinolin-3-yl)-benzyl]-piperidin-1-yl}-cyclopropylmethanone;
{4-[4-(4-chloro-quinolin-3-yl)-benzyl]-piperidin-1-yl}-(3,3-difluoro-cyclobutyl)-methanone;
{4-[4-(4-chloro-quinolin-3-yl)-benzyl]-piperidin-1-yl}-(R)-tetrahydrofuran-2-yl-methanone;
1-{4-[4-(8-methyl-quinolin-7-yl)-benzyl]-piperidin-1-yl}-propan-1-one;
cyclopropyl-{4-[4-(8-methyl-quinolin-7-yl)-benzyl]-piperidin-1-yl}-methanone;
{4-[4-(8-methyl-quinolin-7-yl)-benzyl]-piperidin-1-yl}-(R)-tetrahydro-furan-2-yl-methanone;
1-[4-(4-isoquinolin-3-yl-benzyl)-piperidin-1-yl]-propan-1-one;
cyclopropyl-[4-(4-isoquinolin-3-yl-benzyl)-piperidin-1-yl]-methanone;
[4-(4-isoquinolin-3-yl-benzyl)-piperidin-1-yl]-(R)-tetrahydro-furan-2-yl-methanone;
1-{4-[4-(8-chloro-quinolin-7-yl)-benzyl]-piperidin-1-yl}-propan-1-one;
{4-[4-(8-chloro-quinolin-7-yl)-benzyl]-piperidin-1-yl}-cyclopropylmethanone;
{4-[4-(8-chloro-quinolin-7-yl)-benzyl]-piperidin-1-yl}-(R)-tetrahydrofuran-2-yl-methanone;
1-{4-[4-(8-methoxy-quinolin-7-yl)-benzyl]-piperidin-1-yl}-propan-1-one;
cyclopropyl-{4-[4-(8-methoxy-quinolin-7-yl)-benzyl]-piperidin-1-yl}-methanone;
{4-[4-(8-methoxy-quinolin-7-yl)-benzyl]-piperidin-1-yl}-(R)-tetrahydrofuran-2-yl-methanone;
1-{4-[4-(1-methyl-isoquinolin-6-yl)-benzyl]-piperidin-1-yl}-propan-1-one;
cyclopropyl-{4-[4-(1-methyl-isoquinolin-6-yl)-benzyl]-piperidin-1-yl}-methanone;
{4-[4-(1-methyl-isoquinolin-6-yl)-benzyl]-piperidin-1-yl}-(R)-tetrahydrofuran-2-yl-methanone;
cyclopropyl-{4-[1-(4-quinolin-3-yl-phenyl)-vinyl]-piperidin-1-yl}-methanone;
1-{4-[amino-(4-quinolin-3-yl-phenyl)-methyl]-piperidin-1-yl}-propan-1-one;
1-{4-[(E:Z)-methoxyimino]-(4-quinolin-3-yl-phenyl)-methyl]-piperidin-1-yl}-propan-1-one;
[4-(4-quinolin-3-yl-benzoyl)-piperidin-1-yl]-(R)-tetrahydro-furan-2-yl-methanone;
1-{4-[[methoxyimino]-(4-quinolin-7-yl-phenyl)-methyl]-piperidin-1-yl}-propan-1-one;
1-[4-methyl-4-(4-quinolin-3-yl-benzoyl)-piperidin-1-yl]-propan-1-one;
1-[4-methyl-4-(4-quinolin-3-yl-benzyl)-piperidin-1-yl]-propan-1-one;
4-[1-(4-quinolin-3-yl-phenyl)-ethyl]-piperidine-1-carbaldehyde;
1-(4-{1-[4-(8-methyl-quinolin-7-yl)-phenyl]-ethyl}-piperidin-1-yl)-propan-1-one;
cyclopropyl-(4-{1-[4-(8-methyl-quinolin-7-yl)-phenyl]-ethyl}-piperidin-1-yl)-methanone;
1-(4-{1-[4-(8-methoxy-quinolin-7-yl)-phenyl]-ethyl}-piperidin-1-yl)-propan-1-one;
1-(4-{1-[4-(4-methyl-quinolin-3-yl)-phenyl]-ethyl}-piperidin-1-yl)-propan-1-one;
cyclopropyl-(4-{1-[4-(8-methoxy-quinolin-7-yl)-phenyl]-ethyl}-piperidin-1-yl)-methanone;
1-{4-[1-(4-quinolin-3-yl-phenyl)-ethyl]-piperidin-1-yl}-propan-1-one;
(4-{1-[4-(8-methoxy-quinolin-7-yl)-phenyl]-ethyl}-piperidin-1-yl)-(R)-tetrahydrofuran-2-yl-methanone; mixture of diastereomers;
(4-{1-[4-(8-methyl-quinolin-7-yl)-phenyl]-ethyl}-piperidin-1-yl)-(R)-tetrahydrofuran-2-yl-methanone; mixture of diastereomers;
(4-{1-[4-(4-methyl-quinolin-3-yl)-phenyl]-ethyl}-piperidin-1-yl)-(R)-tetrahydrofuran-2-yl-methanone; mixture of diastereomers;
1-(4-{1-[4-(8-chloro-quinolin-7-yl)-phenyl]-ethyl}-piperidin-1-yl)-propan-1-one;
(4-{1-[4-(8-chloro-quinolin-7-yl)-phenyl]-ethyl}-piperidin-1-yl)-cyclopropyl-methanone;
(4-{1-[4-(8-chloro-quinolin-7-yl)-phenyl]-ethyl}-piperidin-1-yl)-(R)-tetrahydrofuran-2-yl-methanone; mixture of diastereomers;
1-(4-{1-[4-(4-chloro-quinolin-3-yl)-phenyl]-ethyl}-piperidin-1-yl)-propan-1-one;
(4-{1-[4-(4-chloro-quinolin-3-yl)-phenyl]-ethyl}-piperidin-1-yl)-cyclopropylmethanone;
(4-{1-[4-(4-chloro-quinolin-3-yl)-phenyl]-ethyl}-piperidin-1-yl)-(R)-tetrahydrofuran-2-yl-methanone; mixture of diastereomers;
(4-{1-[4-(1-methyl-isoquinolin-6-yl)-phenyl]-cyclopropyl}-piperidin-1-yl)-(R)-tetrahydrofuran-2-yl-methanone;
(4-{1-[4-(8-methyl-quinolin-7-yl)-phenyl]-cyclopropyl}-piperidin-1-yl)-(R)-tetrahydrofuran-2-yl-methanone;
(4-{(2-methoxy-ethoxy)-[4-(8-methyl-quinolin-7-yl)-phenyl]-methyl}-piperidin-1-yl)-(R)-tetrahydrofuran-2-yl-methanone;
1-(4-{(2-methoxy-ethoxy)-[4-(8-methyl-quinolin-7-yl)-phenyl]-methyl}-piperidin-1-yl)-propan-1-one;
(4-{(2-methoxy-ethoxy)-[4-(1-methyl-isoquinolin-6-yl)-phenyl]-methyl}-piperidin-1-yl)-(R)-tetrahydrofuran-2-yl-methanone; mixture of diastereomers;
(4-{(2-methoxy-ethoxy)-[4-(4-methyl-quinolin-3-yl)-phenyl]-methyl}-piperidin-1-yl)-(R)-tetrahydrofuran-2-yl-methanone;
{4-[[4-(8-methyl-quinolin-7-yl)-phenyl]-(3-morpholin-4-yl-propoxy)-methyl]-piperidin-1-yl}-(R)-tetrahydrofuran-2-yl-methanone;
1-{4-[[4-(8-methyl-quinolin-7-yl)-phenyl]-(3-morpholin-4-yl-propoxy)-methyl]-piperidin-1-yl}-propan-1-one;
{4-[4-(1-methyl-isoquinolin-6-yl)-phenyl]-(3-morpholin-4-yl-propoxy)-methyl]-piperidin-1-yl}-(R)-tetrahydrofuran-2-yl-methanone;
{4-[[4-(4-methyl-quinolin-3-yl)-phenyl]-(3-morpholin-4-yl-propoxy)-methyl]-piperidin-1-yl}-(R)-tetrahydrofuran-2-yl-methanone;
{4-[(2-pyrrolidin-1-yl-ethoxy)-(4-quinolin-3-yl-phenyl)-methyl]-piperidin-1-yl}-(R)-tetrahydrofuran-2-yl-methanone;
{4-[4-(8-methyl-quinolin-7-yl)-phenyl]-(2-pyrrolidin-1-yl-ethoxy)-methyl]-piperidin-1-yl}-(R)-tetrahydrofuran-2-yl-methanone;
{4-[4-(1-methyl-isoquinolin-6-yl)-phenyl]-(2-pyrrolidin-1-yl-ethoxy)-methyl]-piperidin-1-yl}-(R)-tetrahydrofuran-2-yl-methanone;
4-[4-(8-methoxy-quinolin-7-yl)-benzyl]-1-((R)-tetrahydro-furan-2-carbonyl)-piperidine-4-carbonitrile;
4-[4-(8-methoxy-quinolin-7-yl)-benzyl]-1-propionyl-piperidine-4-carbonitrile;
{4-[4-(5-methyl-imidazo [1,2-a]pyridin-6-yl)-benzyl]-piperidin-1-yl}-(R)-tetrahydrofuran-2-yl-methanone;
1-{4-[4-(5-methyl-imidazo [1,2-a]pyridin-6-yl)-benzyl]-piperidin-1-yl}-propan-1-one;
cyclopropyl-{4-[4-(5-methyl-imidazo [1,2-a]pyridin-6-yl)-benzyl]-piperidin-1-yl}-methanone;
(1-hydroxy-cyclopropyl)-{4-[4-(5-methyl-imidazo [1,2-a]pyridin-6-yl)-benzyl]-piperidin-1-yl}-methanone;
(R)-(4-fluoro-4-(4-(5-methylimidazo [1,2-a]pyridin-6-yl) benzyl) piperidin-1-yl) (tetrahydrofuran-2-yl) methanone;
2,2,2-trifluoro-1-{4-[2-(4-quinolin-6-yl-phenyl)-1,3-dioxolan-2-yl]-piperidin-1-yl}-ethanone;
cyclopropyl-{4-[2-(4-quinolin-6-yl-phenyl)-1,3-dioxolan-2-yl]-piperidin-1-yl}-methanone;
4-[2-(4-quinolin-6-yl-phenyl)-1,3-dioxolan-2-yl]-piperidine-1-sulfonic acid dimethylamide;
2-methyl-1-{4-[2-(4-quinolin-6-yl-phenyl)-1,3-dioxolan-2-yl]-piperidin-1-yl}-propan-1-one;
4-[2-(4-quinolin-6-yl-phenyl)-1,3-dioxolan-2-yl]-piperidine-1-carboxylic acid dimethylamide;
1-{4-[2-(4-quinolin-6-yl-phenyl)-1,3-dioxolan-2-yl]-piperidin-1-yl}-propan-1-one;
1-{4-[2-(4-quinolin-6-yl-phenyl)-1,3-dioxolan-2-yl]-piperidin-1-yl}-butan-1-one;
1-{4-[2-(4-quinolin-6-yl-phenyl)-1,3-dioxolan-2-yl]-piperidin-1-yl}-ethanone;
4-[2-(4-quinolin-6-yl-phenyl)-1,3-dioxolan-2-yl]-piperidine-1-carboxylic acid cyclopentylamide;
6-(4-{2-[1-(tetrahydropyran-4-yl)-piperidin-4-yl]-1,3-dioxolan-2-yl}-phenyl)-quinoline;
2-methyl-1-[4-(4-quinolin-6-yl-benzoyl)-piperidin-1-yl]-propan-1-one;
2-methyl-1-{4-[2-(4-quinolin-7-yl-phenyl)-1,3-dioxolan-2-yl]-piperidin-1-yl}-propan-1-one;
cyclopropyl-{4-[2-(4-quinolin-7-yl-phenyl)-1,3-dioxolan-2-yl]-piperidin-1-yl}-methanone;
1-{4-[2-(4-quinolin-7-yl-phenyl)-1,3-dioxolan-2-yl]-piperidin-1-yl}-butan-1-one;
1-{4-[2-(4-quinolin-7-yl-phenyl)-1,3-dioxolan-2-yl]-piperidin-1-yl}-propan-1-one;
1-{4-[2-(4-isoquinolin-7-yl-phenyl)-1,3-dioxolan-2-yl]-piperidin-1-yl}-ethanone;
1-{4-[2-(4-isoquinolin-7-yl-phenyl)-1,3-dioxolan-2-yl]-piperidin-1-yl}-propan-1-one;
1-{4-[2-(4-isoquinolin-7-yl-phenyl)-1,3-dioxolan-2-yl]-piperidin-1-yl}-2-methyl-propan-1-one;
1-{4-[2-(4-isoquinolin-6-yl-phenyl)-1,3-dioxolan-2-yl]-piperidin-1-yl}-propan-1-one;
1-{4-[2-(4-isoquinolin-6-yl-phenyl)-1,3-dioxolan-2-yl]-piperidin-1-yl}-2-methyl-propan-1-one;
1-{4-[2-(4-isoquinolin-6-yl-phenyl)-1,3-dioxolan-2-yl]-piperidin-1-yl}-ethanone;
2-methyl-1-{4-[2-(4-quinolin-7-yl-phenyl)-1,3-dioxinan-2-yl]-piperidin-1-yl}-propan-1-one;
cyclopropyl-{4-[2-(4-quinolin-7-yl-phenyl)-1,3-dioxinan-2-yl]-piperidin-1-yl}-methanone;
1-{4-[2-(4-quinolin-7-yl-phenyl)-1,3-dioxinan-2-yl]-piperidin-1-yl}-propan-1-one;
1-[4-(4-quinolin-7-yl-benzoyl)-piperidin-1-yl]-propan-1-one;
1-[4-(2-fluoro-4-isoquinolin-6-yl-benzoyl)-piperidin-1-yl]-propan-1-one;
1-[4-(4-isoquinolin-6-yl-benzoyl)-piperidin-1-yl]-propan-1-one;
1-[4-(2,6-difluoro-4-isoquinolin-6-yl-benzoyl)-piperidin-1-yl]-propan-1-one;
1-{4-[2-(4-quinolin-3-yl-phenyl)-1,3-dioxolan-2-yl]-piperidin-1-yl}-propan-1-one;
2-methyl-1-{4-[2-(4-quinolin-3-yl-phenyl)-1,3-dioxolan-2-yl]-piperidin-1-yl}-propan-1-one;
cyclopropyl-{4-[2-(4-quinolin-3-yl-phenyl)-1,3-dioxolan-2-yl]-piperidin-1-yl}-methanone;
1-[4-(2-fluoro-4-quinolin-7-yl-benzoyl)-piperidin-1-yl]-propan-1-one;
1-[4-(2-fluoro-4-quinolin-3-yl-benzoyl) piperidin-1-yl]propan-1-one;
(4-hydroxy-4-(4-(isoquinolin-3-yl) benzyl) piperidin-1-yl) (isoxazolidin-2-yl) methanone;
[4-hydroxy-4-(4-isoquinolin-3-yl-benzyl)-piperidin-1-yl]-(R)-tetrahydrofuran-2-yl-methanone;
1-[4-hydroxy-4-(4-isoquinolin-6-yl-benzyl)-piperidin-1-yl]-2-methyl-propan-1-one;
1-(4-hydroxy-4-(4-(quinolin-3-yl) benzyl) piperidin-1-yl) propan-1-one;
1-(4-hydroxy-4-(4-(quinolin-3-yl) benzyl) piperidin-1-yl)-2-methylpropan-1-one;
1-(4-hydroxy-4-(4-(quinolin-7-yl) benzyl) piperidin-1-yl) propan-1-one;
1-(4-hydroxy-4-(4-(quinolin-7-yl) benzyl) piperidin-1-yl)-2-methylpropan-1-one;
1-(4-(4-(benzofuran-5-yl) benzyl)-4-hydroxypiperidin-1-yl) propan-1-one;
1-(4-(4-(benzofuran-5-yl) benzyl)-4-hydroxypiperidin-1-yl)-2-methylpropan-1-one;
1-(4-(4-(1H-indol-5-yl) benzyl)-4-hydroxypiperidin-1-yl) propan-1-one;
1-(4-(4-(1H-indol-5-yl) benzyl)-4-hydroxypiperidin-1-yl)-2-methylpropan-1-one;
1-(4-hydroxy-4-(4-(isoquinolin-4-yl) benzyl) piperidin-1-yl) propan-1-one;
1-(4-hydroxy-4-(4-(isoquinolin-4-yl) benzyl) piperidin-1-yl)-2-methylpropan-1-one;
1-(4-hydroxy-4-(4-(isoquinolin-6-yl) benzyl) piperidin-1-yl) propan-1-one;
1-(4-(4-(quinolin-3-yl) benzyl)-5,6-dihydropyridin-1 (2H)-yl) propan-1-one;
1-(4-(4-(quinolin-7-yl) benzyl)-5,6-dihydropyridin-1 (2H)-yl) propan-1-one;
1-(4-(4-(isoquinolin-6-yl) benzyl)-5,6-dihydropyridin-1 (2H)-yl) propan-1-one;
1-(4-fluoro-4-(4-(isoquinolin-4-yl) benzyl) piperidin-1-yl) propan-1-one;
1-(4-(4-(isoquinolin-4-yl) benzyl)-5,6-dihydropyridin-1 (2H)-yl) propan-1-one;
1-(4-(4-(benzofuran-5-yl) benzyl)-4-fluoropiperidin-1-yl) propan-1-one;
1-(4-(4-(benzofuran-5-yl) benzyl)-5,6-dihydropyridin-1 (2H)-yl) propan-1-one;
cyclopropyl(4-(4-(quinolin-3-yl) benzyl)-5,6-dihydropyridin-1 (2H)-yl) methanone;
cyclopropyl(4-(4-(quinolin-7-yl) benzyl)-5,6-dihydropyridin-1 (2H)-yl) methanone;
cyclopropyl(4-(4-(isoquinolin-6-yl) benzyl)-5,6-dihydropyridin-1 (2H)-yl) methanone;
cyclopropyl(4-fluoro-4-(4-(isoquinolin-4-yl) benzyl) piperidin-1-yl) methanone;
cyclopropyl(4-(4-(isoquinolin-4-yl) benzyl)-5,6-dihydropyridin-1 (2H)-yl) methanone;
(4-(4-(benzofuran-5-yl) benzyl)-4-fluoropiperidin-1-yl) (cyclopropyl) methanone;
(4-(4-(benzofuran-5-yl) benzyl)-5,6-dihydropyridin-1 (2H)-yl) (cyclopropyl)-methanone;
(R)-(4-(4-(4-methylquinolin-3-yl) benzyl)-5,6-dihydropyridin-1 (2H)-yl) (tetrahydrofuran-2-yl) methanone;
cyclopropyl(4-(4-(8-methylquinolin-7-yl) benzyl)-3,6-dihydropyridin-1 (2H)-yl) methanone;
1-(4-(4-(8-methylquinolin-7-yl) benzyl)-3,6-dihydropyridin-1 (2H)-yl) propan-1-one;
(R)-(4-(4-(quinolin-7-yl) benzyl)-5,6-dihydropyridin-1 (2H)-yl) (tetrahydrofuran-2-yl) methanone;
(R)-(4-(4-(quinolin-3-yl) benzyl)-5,6-dihydropyridin-1 (2H)-yl) (tetrahydrofuran-2-yl) methanone;
cyclopropyl(4-(4-(4-methylquinolin-3-yl) benzyl)-5,6-dihydropyridin-1 (2H)-yl) methanone;
1-(4-(4-(4-chloroquinolin-3-yl) benzyl)-3,6-dihydropyridin-1 (2H)-yl) propan-1-one;
1-(4-(4-(4-Methylquinolin-3-yl) benzyl)-5,6-dihydropyridin-1 (2H)-yl) propan-1-one;
(4-(4-(4-chloroquinolin-3-yl) benzyl)-3,6-dihydropyridin-1 (2H)-yl) (cyclopropyl)-methanone;
(R)-(4-(4-(8-methylquinolin-7-yl) benzyl)-3,6-dihydropyridin-1 (2H)-yl) (tetrahydro-furan-2-yl) methanone;
(R)-(4-(4-(4-chloroquinolin-3-yl) benzyl)-3,6-dihydropyridin-1 (2H)-yl) (tetrahydrofuran-2-yl) methanone;
1-{4-[1-ethoxy-1-(4-quinolin-3-yl-phenyl)-ethyl]-piperidin-1-yl}-propan-1-one;
cyclopropyl-{4-[1-ethoxy-1-(4-quinolin-3-yl-phenyl)-ethyl]-piperidin-1-yl}-methanone;
1-{4-[1-methoxy-1-(4-quinolin-3-yl-phenyl)-ethyl]-piperidin-1-yl}-propan-1-one;
cyclopropyl-{4-[1-methoxy-1-(4-quinolin-3-yl-phenyl)-ethyl]-piperidin-1-yl}-methanone;
1-{4-[1-methoxy-1-(4-quinolin-3-yl-phenyl)-propyl]-piperidin-1-yl}-propan-1-one;
cyclopropyl-{4-[1-methoxy-1-(4-quinolin-3-yl-phenyl)-propyl]-piperidin-1-yl}-methanone;
1-{4-[1-methoxy-1-(4-quinolin-7-yl-phenyl)-ethyl]-piperidin-1-yl}-propan-1-one;
cyclopropyl-{4-[1-methoxy-1-(4-quinolin-7-yl-phenyl)-ethyl]-piperidin-1-yl}-methanone;
1-{4-[1-ethoxy-1-(4-quinolin-7-yl-phenyl)-ethyl]-piperidin-1-yl}-propan-1-one;
cyclopropyl-{4-[1-ethoxy-1-(4-quinolin-7-yl-phenyl)-ethyl]-piperidin-1-yl}-methanone;
1-{4-[1-methoxy-1-(4-quinolin-7-yl-phenyl)-propyl]-piperidin-1-yl}-propan-1-one;
cyclopropyl-{4-[1-methoxy-1-(4-quinolin-7-yl-phenyl)-propyl]-piperidin-1-yl}-methanone;
1-propionyl-4-(4-quinolin-3-yl-benzyl)-piperidin-3-one;
1-{4-fluoro-4-[4-(8-methyl-quinolin-7-yl)-benzoyl]-piperidin-1-yl}-propan-1-one;
1-(4-fluoro-4-{methoxy-[4-(8-methyl-quinolin-7-yl)-phenyl]-methyl}-piperidin-1-yl)-propan-1-one;
1-(4-fluoro-4-{(2-methoxy-ethoxy)-[4-(8-methyl-quinolin-7-yl)-phenyl]-methyl}-piperidin-1-yl)-propan-1-one;
1-{4-fluoro-4-[4-(8-methyl-quinolin-7-yl)-phenyl]-(2-morpholin-4-yl-ethoxy)-methyl]-piperidin-1-yl}-propan-1-one;
1-(4-(1-(4-(1,2,3,4-tetrahydroquinolin-7-yl) phenyl) ethyl) piperidin-1-yl) propan-1-one;
1-{4-[hydroxy-(4-quinolin-6-yl-phenyl)-methyl]-piperidin-1-yl}-2-methylpropan-1-one;
1-{4-[hydroxy-(4-quinolin-7-yl-phenyl)-methyl]-piperidin-1-yl}-propan-1-one;
1-{4-[1-hydroxy-1-(4-quinolin-7-yl-phenyl)-ethyl]-piperidin-1-yl}-propan-1-one;
1-{4-[(2-fluoro-4-isoquinolin-6-yl-phenyl)-hydroxymethyl]-piperidin-1-yl}-propan-1-one;
1-{4-[hydroxy-(4-isoquinolin-6-yl-phenyl)-methyl]-piperidin-1-yl}-propan-1-one;
1-{4-[1-hydroxy-1-(4-isoquinolin-6-yl-phenyl)-ethyl]-piperidin-1-yl}-propan-1-one;
1-{4-[1-(2-fluoro-4-isoquinolin-6-yl-phenyl)-1-hydroxy-ethyl]-piperidin-1-yl}-propan-1-one;
1-{3-[1-hydroxy-1-(4-isoquinolin-6-yl-phenyl)-ethyl]-pyrrolidin-1-yl}-propan-1-one;
1-{4-[2-(4′-dimethylaminomethyl-biphenyl-4-yl)-1,3-dioxolan-2-yl]piperidin-1-yl}-2-methyl-propan-1-one;
1-{4-[2-(4′-dimethylaminomethyl-biphenyl-4-yl)-1,3-dioxolan-2-yl]-piperidin-1-yl}-propan-1-one;
cyclopropyl-{4-[2-(4′-dimethylaminomethyl-biphenyl-4-yl)-1,3-dioxolan-2-yl]-piperidin-1-yl}-methanone;
1-(4-(4-(benzofuran-2-yl) benzyl)-4-hydroxypiperidin-1-yl) propan-1-one;
1-(4-(4-(benzofuran-2-yl) benzyl)-4-hydroxypiperidin-1-yl)-2-methylpropan-1-one;
1-{4-fluoro-4-[4-(8-methyl-quinolin-7-yl)-benzoyl]-piperidin-1-yl}-propan-1-one;
N-[(1-propionyl-piperidin-4-yl)-(4-quinolin-3-yl-phenyl)-methyl]-acetamide;
N-[(1-propionyl-piperidin-4-yl)-(4-quinolin-3-yl-phenyl)-methyl]-formamide;
4-[1-(4-quinolin-3-yl-phenyl)-ethyl]-piperidine-1-carboxylic acid tert-butyl ester;
4-[2-(4-quinolin-6-yl-phenyl)-1,3-dioxolan-2-yl]-piperidine-1-carboxylic acid ethyl ester;
1-(4-{difluoro-[4-(4-methyl-quinolin-3-yl)-phenyl]-methyl}-piperidin-1-yl)-propan-1-one;
(R)-(4-(4-(4-chloroquinolin-3-yl) benzyl)-3,6-dihydropyridin-1 (2H)-yl) (tetrahydro-furan-2-yl) methanone;
1-{4-[1-ethoxy-1-(4-quinolin-3-yl-phenyl)-ethyl]-piperidin-1-yl}-propan-1-one;
1-{4-[1-(2-fluoro-4-isoquinolin-6-yl-phenyl)-1-hydroxy-ethyl]-piperidin-1-yl}-propan-1-one;
4-(2-fluoro-4-quinolin-3-yl-benzoyl) piperidine-1-carboxylic acid methyl ester;
or 1-[3-(4-isoquinolin-6-yl-benzoyl)-pyrrolidin-1-yl]-propan-1-one.