IP Library › Granted Patent US 12,441,702
Granted Patent B2
US 12,441,702 · App. 18/526,380 · Granted Oct 14, 2025

Substituted 4-benzyl and 4-benzoyl piperidine derivates

Inventors: Nadine C. Becknell (Coatesville, PA); Reddeppa Reddy Dandu (Downingtown, PA); Bruce D. Dorsey (Ambler, PA); Dimitar B. Gotchev (Hatboro, PA); Robert L. Hudkins (Chester Springs, PA); Linda Weinberg (King of Prussia, PA); Craig A. Zificsak (Downingtown, PA)
Assignee: Cephalon LLC
C07D401/10C07D405/10C07D405/14C07D413/14C07D471/04
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Quick Facts
Patent No.
US 12,441,702
App. No.
18/526,380
Granted
Oct 14, 2025
Kind
B2
Abstract

Described herein are 1,4-substituted piperidine compounds according to Formula I that have demonstrated activity as fatty acid synthase inhibitors. Also described herein are pharmaceutical compositions containing the described 1,4-substituted piperidine compounds. Also described herein are methods of treating diseases mediated by fatty acid synthase, by administering one or more of the compounds or pharmaceutical formulations described herein. Also described herein are methods of synthesizing the described 1,4-substituted piperidine compounds and synthetic intermediates useful in those syntheses.

Claims (283)

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.

2. The method of claim 1 , wherein the disorder mediated by fatty acid synthase is drug-induced body weight gain.

3. The method of claim 2 , wherein the drug-induced body weight gain is atypical antipsychotic-induced weight gain.

4. The method of claim 3 , wherein the antipsychotic agent is selected from clozapine, risperidone, aripiprazole, olanzapine, quetiapine and ziprasidone and combinations thereof.

5. The method of claim 1 , wherein the disorder mediated by fatty acid synthase is a metabolic disease.

6. The method of claim 5 , wherein the metabolic disease is NASH (non-alcoholic hepatic steatosis) or Type 2 diabetes.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 22, 2025
From: 89BIO LTD
To: CEPHALON LLC
Reel/Frame 071194/0011 →
Continuity (4)
Division 17175751 · Feb 12, 2021
Continuation 15735811
Provisional Application 62181391 · Jun 18, 2015
Related Publication 20240166625A1 · May 23, 2024
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