IP Library › Granted Patent US 12,448,392
Granted Patent B2
US 12,448,392 · App. 18/526,408 · Granted Oct 21, 2025

Spiropiperidine derivatives

Inventors: Robert L. Hudkins (Chester Springs, PA); David B. Whitman (Phoenixville, PA); Craig A. Zificsak (Downingtown, PA); Allison L. Zulli (Chesterbrook, PA); Melody McWherter (Boyertown, PA)
Assignee: Cephalon LLC
C07D491/107C07D491/113
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Quick Facts
Patent No.
US 12,448,392
App. No.
18/526,408
Granted
Oct 21, 2025
Kind
B2
Abstract

Described herein are spiropiperidine compounds according to Formula I that have demonstrated activity as fatty acid synthase inhibitors. Also described herein are pharmaceutical compositions containing the described spiropiperidine compounds, and 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 compounds described, including the described spiropiperidine compounds and synthetic intermediates that are useful in those syntheses.

Claims (20)

1. A method of treating a subject suffering from a disorder mediated by fatty acid synthase, comprising administering to the subject a therapeutically effective amount of a compound that is

or a pharmaceutically acceptable salt thereof.

2. The method according to claim 1 , 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, cancer, or cancer metastasis.

3. The method according to claim 2 , wherein the disorder mediated by fatty acid synthase is drug induced body weight gain, wherein said drug induced body weight gain is weight gain associated with drug therapy with an antipsychotic agent.

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

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

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

7. The method according to claim 6 , wherein said metabolic disease is non-alcoholic hepatic steatosis (NASH).

8. The method according to claim 1 , wherein the disorder mediated by fatty acid synthase is cancer.

9. The method according to claim 8 , wherein said cancer is human breast, ovarian, prostate, colon, lung, bladder, stomach or kidney cancer.

10. A method of treating a subject suffering from a disorder mediated by fatty acid synthase, comprising administering to the subject a pharmaceutical composition comprising a therapeutically effective amount of a compound that is

or a pharmaceutically acceptable salt thereof.

11. The method according to claim 10 , 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, cancer, or cancer metastasis.

12. The method according to claim 11 , wherein the disorder mediated by fatty acid synthase is drug induced body weight gain, wherein said drug induced body weight gain is weight gain associated with drug therapy with an antipsychotic agent.

13. The method of claim 12 , wherein the antipsychotic agent is selected from clozapine, risperidone, aripiprazole, olanzapine, quetiapine, ziprasidone, and combinations thereof.

14. The method according to claim 10 , wherein the disorder mediated by fatty acid synthase is a metabolic disease.

15. The method according to claim 14 , wherein said metabolic disease is non-alcoholic hepatic steatosis (NASH), or Type 2 diabetes.

16. The method according to claim 14 , wherein said metabolic disease is non-alcoholic hepatic steatosis (NASH).

17. The method according to claim 10 , wherein the disorder mediated by fatty acid synthase is cancer.

18. The method according to claim 17 , wherein said cancer is human breast, ovarian, prostate, colon, lung, bladder, stomach or kidney cancer.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 22, 2025
From: 89BIO LTD
To: CEPHALON LLC
Reel/Frame 071194/0233 →
Continuity (4)
Division 17329525 · May 25, 2021
Continuation 16469840
Provisional Application 62434167 · Dec 14, 2016
Related Publication 20240166661A1 · May 23, 2024
References Cited (30)
US 11046707B2 · Hudkins · 2021 [cited by examiner]
US 20070021453A1 · Yamakawa et al. · 2007 [cited by applicant]
US 20070117823A1 · Antel et al. · 2007 [cited by applicant]
US 20080171761A1 · Iino et al. · 2008 [cited by applicant]
US 20090270436A1 · Iino et al. · 2009 [cited by applicant]
US 20110071131A1 · Bacon et al. · 2011 [cited by applicant]
US 20190181928A1 · Pan et al. · 2019 [cited by applicant]
CN 103304571A · 2013 [cited by applicant]
EP 1951725B1 · 2010 [cited by applicant]
JP 2009502785A · 2009 [cited by applicant]
JP 2009515928A · 2009 [cited by applicant]
JP 2010515733A · 2010 [cited by applicant]
JP 2010515734A · 2010 [cited by applicant]
JP 2019531624A · 2019 [cited by applicant]
WO 9418204A1 · 1994 [cited by applicant]
WO 2007054580A1 · 2007 [cited by applicant]
WO 2010002010A1 · 2010 [cited by applicant]
WO 2012161119A1 · 2012 [cited by applicant]
Berod et al., De Novo Fatty Acid Synthesis Controls the Fate Between Regulatory T and T Helper 17 Cells, Nature Medicine, Nov. 2014, 20(11), 1327-1333. [cited by applicant]
Chung et al., A Fluorescence-Based Thiol Quantification Assay for Ultra-High-Throughput Screening for Inhibitors of Coenzyme A Production, Assay and Drug Development Technologies, 2008, vol. 6, No. 3: 361-374. [cited by applicant]
Everts et al., TLR-Driven Early Glycolytic Reprogramming via the Kinases TBK1-IKK? supports the anabolic Demands of Dendritic Cell Activation, Nature Immunology, 2014, 15, 323-332. [cited by applicant]
Hunt et al., mRNA Stability and Overexpression of Fatty Acid Synthase in Human Breast Cancer Cell Lines, Anticancer Research 27, 2007, 27-34. [cited by applicant]
Kuhajda, F.P., Fatty Acid Synthase and Cancer: New Application of an Old Pathway, Cancer Research, Jun. 2006, 66 (12), 5977-5980. [cited by applicant]
Kuhajda, F.P., Fatty-acid Synthase and Human Cancer: New Perspectives on its Role in Tumor Biology, Nutrition, 2000, vol. 16, Issue 3, 202-208. [cited by applicant]
Menendez et al., Fatty Acid Synthase and the Lipogenic Phenotype in Cancer Pathogenesis, Nature Reviews Cancer, Oct. 2007, 7, 763-777. [cited by applicant]
Munger et al, Systems-Level Metabolic Flux Profiling Identifies Fatty Acide Synthesis as a Target for Antiviral Therapy, Nature Biotechnology, 2008, 26, 1179-1186. [cited by applicant]
Nasheri et al., Modulation of Fatty Acid Synthase Enzyme Activity and Expression During Hepatitis C Virus Replication, Chemistry and Biology, Apr. 18, 2013, 20: 570-582. [cited by applicant]
Pollak, M., Targeting Oxidative Phosphorylation: Why, When and How, Cancer Cell, Mar. 18, 2013, 23(3): 263-264. [cited by applicant]
Shen et at. “Discovery of spirocyclic secondary amine-derived tertiary ureas as highly potent selective and bioavailable soluble epoxide hydrolase inhibitors”, Bioorganic & Medicinal Chemistry Letters. 2009. vol. 19, p.… [cited by applicant]
Sounni, NE et al., Blocking Lipid Synthesis Overcomes Tumor Regrowth and Metastasis After Angiogenic Therapy Withdrawal; (Aug. 5, 2014) Cell Metabolism 20(2), 280-294. [cited by applicant]