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Oveporexton

CAS 2460722-04-5

MF C23H25F5N2O4S MW 520.5

N-[(2S,3R)-2-[[3-(3,5-difluorophenyl)-2-fluorophenyl]methyl]-4,4-difluoro-1-(2-hydroxy-2-methylpropanoyl)pyrrolidin-3-yl]ethanesulfonamide

N-[(2S,3R)-1-(2-ヒドロキシ-2-メチルプロピオニル)-2-(2,3′,5′-トリフルオロビフェニル-3-イルメチル)-4,4-ジフルオロピロリジン-3-イル]エタンスルホンアミド

ETHANESULFONAMIDE, N-((2S,3R)-4,4-DIFLUORO-1-(2-HYDROXY-2-METHYL-1-OXOPROPYL)-2-((2,3′,5′-TRIFLUORO(1,1′-BIPHENYL)-3-YL)METHYL)-3-PYRROLIDINYL)-

N-[(2S,3R)-2-[[3-(3,5-difluorophenyl)-2-fluorophenyl]methyl]-4,4-difluoro-1-(2-hydroxy-2-methylpropanoyl)pyrrolidin-3-yl]ethanesulfonamide

N-{(2S,3R)-4,4-difluoro-1-(2-hydroxy-2-methylpropanoyl)-2-[(2,3′,5′-trifluoro-[1,1′-biphenyl]-3-yl)methyl]pyrrolidin-3-yl}ethane-1-sulfonamide
orexin type 2 receptor agonist, TAK-861, TAK 861, 59MF6P2ATF

Oveporexton is a small molecule drug. The usage of the INN stem ‘-orexton’ in the name indicates that Oveporexton is a orexin receptor agonist. Oveporexton has a monoisotopic molecular weight of 520.15 Da.

Oveporexton (INNTooltip International Nonproprietary Name; developmental code name TAK-861) is an orexin receptor agonist and wakefulness-promoting agent which is under development for the treatment of narcolepsy (types 1 and 2) and idiopathic hypersomnia.^[1]^[2]^[3] It is taken by mouth.^[1]^[2]

The drug acts as a selective agonist of the orexin OX₂ receptor.^[1]^[2] It has wakefulness-promoting effects in animals, including in rodents and monkeys.^[2] In addition, oveporexton has been found to be effective in the treatment of narcolepsy and cataplexy in phase 3 clinical trials in humans.^[4]^[5]^[6] The drug is a first-in-class medication and targets the root symptomatic cause of narcolepsy (type 1) by remediating the orexin (hypocretin) deficiency that is present in the condition.^[7]^[8]^[9]

Oveporexton is being developed by Takeda.^[1] As of July 2025, it has completed phase 3 clinical trials for treatment of narcolepsy, whereas no recent development has been reported for treatment of idiopathic hypersomnia.^[1]^[5]^[10] Takeda plans to submit a New Drug Application (NDA) of oveporexton for the treatment of narcolepsy to the United States Food and Drug Administration (FDA) in 2025.^[5] Oveporexton is a follow-on and replacement compound for Takeda’s earlier lead drug danavorexton (TAK-925), which is administered intravenously and stopped being developed due to unexpected liver toxicity findings.^[10]

A Trial of TAK-861 for the Treatment of Narcolepsy With CataplexyCTID: NCT07363720Phase: Phase 3Status: Not yet recruitingDate: 2026-01-23Conditions: Narcolepsy Type 1 (NT1); Narcolepsy With CataplexyInterventions: PlaceboLinked Compound CID: 154617563
A Study of TAK-861 for the Treatment of Selected Central Hypersomnia ConditionsCTID: NCT05816382Phase: Phase 2/Phase 3Status: RecruitingDate: 2025-12-01Conditions: Narcolepsy Type 1Interventions: TAK-861Linked Compound CID: 154617563
A Study of TAK-861 in People With Narcolepsy Type 1CTID: NCT06505031Phase: Phase 3Status: CompletedDate: 2025-09-15Conditions: Narcolepsy Type 1Interventions: PlaceboLinked Compound CID: 154617563
A Study of TAK-861 for the Treatment of Narcolepsy Type 1CTID: NCT06470828Phase: Phase 3Status: CompletedDate: 2025-07-01Conditions: Narcolepsy Type 1Interventions: PlaceboLinked Compound CID: 154617563
A Study of TAK-861 in Participants With Narcolepsy Type 1CTID: NCT05687903Phase: Phase 2Status: CompletedDate: 2025-01-09Conditions: Narcolepsy Type 1Interventions: PlaceboLinked Compound CID: 154617563
A Randomized, Double-blind, Placebo-Controlled Study to Evaluate the Efficacy, Safety, and Tolerability of TAK-861 for the Treatment of Narcolepsy With Cataplexy (Narcolepsy Type 1)EudraCT: 2022-001654-38Phase: Phase 2Status: CompletedDate: 2023-05-26Linked Compound CID: 154617563
A Long-term Extension Study to Evaluate the Safety and Tolerability of TAK-861 in Participants With Selected Central Hypersomnia ConditionsEudraCT: 2022-002965-13Phase: Phase 2, Phase 3Status: Trial now transitionedDate: 2023-04-11Linked Compound CID: 154617563
A Randomized, Double-blind, Placebo-Controlled Study to Evaluate the Efficacy, Safety, and Tolerability of TAK-861 for the Treatment of Narcolepsy Without Cataplexy (Narcolepsy Type 2)EudraCT: 2022-002966-34Phase: Phase 2Status: CompletedDate: 2023-03-20Linked Compound CID: 154617563

SYN

https://patents.google.com/patent/US11028048B2/en

SYN

[US20210276949]

https://patentscope.wipo.int/search/en/detail.jsf?docId=US335376985&_cid=P12-MM5PM8-70991-1

Example 3

N-{(2S,3R)-4,4-difluoro-1-(2-hydroxy-2-methylpropanoyl)-2-. [(2,3′,5′-trifluoro[1,1′-biphenyl]-3-yl)methyl]pyrrolidin-3-yl}ethanesulfonamide

A) tert-butyl (2S,3R)-3-(ethylsulfonamido)-4,4-difluoro-2-((2,3′,5′-trifluoro-[1,1′-biphenyl]-3-yl)methyl)pyrrolidine-1-carboxylate

To a mixture of tert-butyl (2S,3R)-2-(3-chloro-2-fluorobenzyl)-3-(ethylsulfonamido)-4,4-difluoropyrrolidine-1-carboxylate (3.70 g), (3,5-difluorophenyl)boronic acid (2.56 g) and 1 M aqueous potassium phosphate solution (24.3 mL) in DME (50 mL) was added XPhos Pd G3 (0.343 g) at room temperature. The mixture was stirred at 90° C. under nitrogen atmosphere for 15 h. The reaction mixture was poured into water and extracted with EtOAc. The organic layer was washed with saturated brine, dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, EOAc/hexane) to give the title compound (3.30 g).

MS: [M−H] ⁻533.2.

B) N-((2S,3R)-4,4-difluoro-2-((2,3′,5′-trifluoro-[1,1′-biphenyl]-3-yl)methyl)pyrrolidin-3-yl)ethanesulfonamide hydrochloride

A mixture of tert-butyl (2S,3R)-3-(ethylsulfonamido)-4,4-difluoro-2-((2,3′,5′-trifluoro-[1,1′-biphenyl]-3-yl)methyl)pyrrolidine-1-carboxylate (3.30 g) and 4 M HCl/CPME solution (30 mL) was stirred overnight at room temperature. By filtration, the title compound (2.86 g) was obtained.

MS: [M+H] ⁺435.1.

C) N-{(2S,3R)-4,4-difluoro-1-(2-hydroxy-2-methylpropanoyl)-2-[(2,3′,5′-trifluoro[1,1′-biphenyl]-3-yl)methyl]pyrrolidin-3-yl}ethanesulfonamide

To a mixture of N-((2S,3R)-4,4-difluoro-2-((2,3′,5′-trifluoro-[1,1′-biphenyl]-3-yl)methyl)pyrrolidin-3-yl)ethanesulfonamide hydrochloride (200 mg) and DIPEA (0.367 ml) in THF (3 mL) was added alpha-acetoxy-isobutyryl chloride (0.074 ml) at 0° C., and the mixture was stirred at same temperature for 10 min. To the mixture were added water (1 ml) and 4 M lithium hydroxide solution (1.06 ml), and the mixture was stirred overnight at room temperature. The mixture was diluted with saturated brine and extracted with EtOAc. The extract was dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, EtOAc/hexane) and recrystallized from EtOAc/hexane to give the title compound (154 mg).

¹H NMR (400 MHz, CDCl ₃) δ 1.32-1.40 (9H, m), 2.27-2.54 (1H, m), 2.88-3.16 (4H, m), 4.02-4.49 (3H, m), 4.86-5.20 (2H, m), 6.78-6.86 (1H, m), 7.02-7.10 (2H, m), 7.16-7.22 (1H, m), 7.27-7.31 (1H, m), 7.35-7.43 (1H, m).

PAT

https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2025229584&_cid=P12-MM5PIO-68796-2

N-{(2S,3R)-4,4-difluoro-l-(2-hydroxy-2-methylpropanoyl)-2-[(2,3′,5′-trifluoro[l,l’-biphenyl]-3-yl)methyl]pyrrolidin-3-yl}ethanesulfonamide, (hereafter referred as to “Compound A”) is described in U.S. Patent No. 11,028,048.

Compound A

PAT

Heterocyclic compound and use thereofPublication Number: US-12415782-B2Priority Date: 2019-01-31Grant Date: 2025-09-16Linked Compounds: 1,196Linked Substances: 1,265
Heterocyclic compound and use thereofPublication Number: US-2025243156-A1Priority Date: 2019-01-31Linked Compounds: 1,190Linked Substances: 1,259
Heterocyclic compound and use thereofPublication Number: TW-202043196-APriority Date: 2019-01-31Linked Compounds: 572Linked Substances: 640
Heterocyclic compound and use thereofPublication Number: US-12421188-B2Patent Family: AR-117916-A1; AU-2020215380-A1; AU-2020215380-A2; AU-2020215380-B2; BR-112021014180-A2; CA-3124536-A1; CL-2021001973-A1; CN-113395993-A; CN-113395993-B; CN-118271297-A; CN-118271298-A; CN-118290408-A; CN-118344346-A; CN-118420600-A; CO-2021011188-A2; DK-3917616-T3; EA-202192138-A1; EC-SP21056325-A; EP-3917616-A1; EP-3917616-B1; EP-4578853-A2; EP-4578853-A3; ES-3037650-T3; FI-3917616-T3; HR-P20250785-T1; HU-E071890-T2; IL-284073-A; IL-284073-B1; IL-284073-B2; JP-2022519331-A; JP-2023078426-A; JP-7253640-B2; JP-7502512-B2; KR-20210121080-A; LT-3917616-T; MX-2021008241-A; PE-20211700-A1; PH-12021551846-A1; PL-3917616-T3; PT-3917616-T; RS-67170-B1; SG-11202106791X-A; SI-3917616-T1; TW-202043196-A; TW-I832962-B; US-11028048-B2; US-12404237-B2; US-12415782-B2; US-12421188-B2; US-2020247747-A1; US-2021276949-A1; US-2023040770-A1; US-2024360080-A1; US-2025243156-A1; US-2025243157-A1; US-2025243158-A1; WO-2020158958-A1; ZA-202106304-BPriority Date: 2019-01-31Grant Date: 2025-09-23Inventor(s): HATTORI YASUSHI; MIYANOHANA YUHEI; KAJITA YUICHI; KOIKE TATSUKI; HOASHI YASUTAKA; …Assignee(s): TAKEDA PHARMACEUTICALS COClassification: C07D207/14; C07D403/06; C07D407/08; C07D417/06Abstract: The present invention provides a heterocyclic compound having an orexin type 2 receptor agonist activity.A compound represented by the formula (I):wherein each symbol is as described in the specification, or a salt thereof has an orexin type 2 receptor agonist activity, and is useful as an agent for the prophylaxis or treatment of narcolepsy.Linked Compounds: 1,190Linked Substances: 1,259
Heterocyclic compounds and their usePublication Number: CN-113395993-BPriority Date: 2019-01-31Grant Date: 2024-02-20Linked Compounds: 1,092Linked Substances: 1,328
Heterocyclic compound and use thereofPublication Number: US-2024360080-A1Priority Date: 2019-01-31Linked Compounds: 1,194Linked Substances: 1,262
Heterocyclic compounds and use thereofPublication Number: EP-3917616-B1Priority Date: 2019-01-31Grant Date: 2025-06-11Linked Compounds: 1,184Linked Substances: 1,210
Method of treating excessive sleepiness and/or cataplexy using n-{2-(([1,1â€²-biphenyl]-3-yl)methyl)pyrrolidin-3-yl}sulfonamide derivativesPublication Number: US-12404237-B2Priority Date: 2019-01-31Grant Date: 2025-09-02Linked Compounds: 1,196Linked Substances: 1,266
Heterocyclic compound and use thereofPublication Number: EP-4578853-A2Priority Date: 2019-01-31Linked Compounds: 1,178Linked Substances: 1,202
Heterocyclic compound and use thereofPublication Number: US-2023040770-A1Priority Date: 2019-01-31Linked Compounds: 1,815Linked Substances: 3,447
Heterocyclic compound and use thereofPublication Number: US-2025243158-A1Priority Date: 2019-01-31Linked Compounds: 1,196Linked Substances: 1,264
Heterocyclic compound and use thereofPublication Number: US-2021276949-A1Priority Date: 2019-01-31Linked Compounds: 1,762Linked Substances: 3,038
COMPOUND, DRUG, METHOD FOR ACTIVATING AN OREXIN TYPE 2 RECEPTOR IN A MAMMAL, METHOD FOR PROPHYLAXIS OR TREATMENT OF NARCOLEPSY IN A MAMMALIAN, AND, USE OF A COMPOUNDPublication Number: BR-112021014180-A2Priority Date: 2019-01-31Linked Compounds: 649Linked Substances: 725
Heterocyclic compound and use thereofPublication Number: US-2025243157-A1Priority Date: 2019-01-31Linked Compounds: 1,196Linked Substances: 1,266
Heterocyclic compounds and their usePublication Number: CN-118271298-APriority Date: 2019-01-31Linked Compounds: 1,252Linked Substances: 2,011
Heterocyclic compounds and uses thereofPublication Number: CN-118344346-APriority Date: 2019-01-31Linked Compounds: 1,247Linked Substances: 2,010
Heterocyclic compounds and their usePublication Number: CN-118420600-APriority Date: 2019-01-31Linked Compounds: 897Linked Substances: 1,440
Heterocyclic compounds and their usesPublication Number: JP-7502512-B2Priority Date: 2019-01-31Grant Date: 2024-06-18Linked Compounds: 672Linked Substances: 744
Use of an orexin 2 receptor agonist for improving respiratory function during sleepPublication Number: TW-202502342-APriority Date: 2023-06-02Linked Compounds: 36Linked Substances: 51
Heterocyclic compounds and uses thereofPublication Number: CN-118271297-APriority Date: 2019-01-31Linked Compounds: 1,220Linked Substances: 1,815
Heterocyclic compounds and uses thereofPublication Number: CN-118290408-APriority Date: 2019-01-31Linked Compounds: 1,181Linked Substances: 1,726
Heterocyclic compound and use thereofPublication Number: US-2020247747-A1Priority Date: 2019-01-31Linked Compounds: 1,790Linked Substances: 3,069
Heterocyclic compound and use thereofPublication Number: US-11028048-B2Priority Date: 2019-01-31Grant Date: 2021-06-08Linked Compounds: 1,788Linked Substances: 3,059

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References

“Oveporexton”. AdisInsight. 16 December 2024. Retrieved 26 February 2025.
Mitsukawa K, Terada M, Yamada R, Monjo T, Hiyoshi T, Nakakariya M, et al. (September 2024). “TAK-861, a potent, orally available orexin receptor 2-selective agonist, produces wakefulness in monkeys and improves narcolepsy-like phenotypes in mouse models”. Scientific Reports. 14 (1) 20838. Bibcode:2024NatSR..1420838M. doi:10.1038/s41598-024-70594-1. PMC 11379823. PMID 39242684.
Kallweit MS, Kallweit NP, Kallweit U (29 November 2023). “Pharmacological Treatments of Sleep–Wake Disorders: Update 2023”. Clinical and Translational Neuroscience. 7 (4): 42. doi:10.3390/ctn7040042. ISSN 2514-183X.
Walters J (7 October 2025). “Positive Data Presentation on Oveporexton for Narcolepsy”. Psychiatric Times. Retrieved 7 October 2025.
Beaney A (14 July 2025). “Takeda’s oral narcolepsy drug shines in two Phase III trials”. Clinical Trials Arena. Retrieved 7 October 2025.
Dauvilliers Y, Plazzi G, Mignot E, Lammers GJ, Del Río Villegas R, Khatami R, et al. (May 2025). “Oveporexton, an Oral Orexin Receptor 2-Selective Agonist, in Narcolepsy Type 1”. The New England Journal of Medicine. 392 (19): 1905–1916. doi:10.1056/NEJMoa2405847. PMID 40367374.
Abad VC (2023). “Pharmacological options for narcolepsy: are they the way forward?”. Expert Rev Neurother. 23 (9): 819–834. doi:10.1080/14737175.2023.2249234. PMID 37585269.
Matsuyama K (8 September 2025). “Takeda Nears First Therapy for Narcolepsy’s Root Cause”. Bloomberg.com. Archived from the original on 8 September 2025. Retrieved 7 October 2025.
Vinluan F (9 September 2025). “Takeda Is Waking Up the Narcolepsy Market With First-in-Class Drug, But Alkermes Is on Its Heels”. MedCity News. Retrieved 7 October 2025.
Mullard A (September 2025). “Leading orexin receptor agonist clears phase III for narcolepsy”. Nat Rev Drug Discov. 24 (9): 655. doi:10.1038/d41573-025-00137-4. PMID 40775090.

Clinical data

Other names	TAK-861; TAK861
Routes of administration	Oral^[1]^[2]
Drug class	Orexin OX₂ receptor agonist; Wakefulness-promoting agent
Identifiers
IUPAC name
CAS Number	2460722-04-5
PubChem CID	154617563
ChemSpider	130299567
UNII	59MF6P2ATF
KEGG	D13223
Chemical and physical data
Formula	C₂₃H₂₅F₅N₂O₄S
Molar mass	520.52 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES
InChI

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Tags: orexin type 2 receptor agonist, oveporexton, TAK 861, TAK-861

By DR ANTHONY MELVIN CRASTO Ph.D in Uncategorized on February 28, 2026.

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DR ANTHONY MELVIN CRASTO Ph.D

DR ANTHONY MELVIN CRASTO, Born in Mumbai in 1964 and graduated from Mumbai University, Completed his Ph.D from ICT, 1991,Matunga, Mumbai, India, in Organic Chemistry, The thesis topic was Synthesis of Novel Pyrethroid Analogues, Currently he is working with AFRICURE PHARMA, ROW2TECH, NIPER-G, Department of Pharmaceuticals, Ministry of Chemicals and Fertilizers, Govt. of India as ADVISOR, earlier assignment was with GLENMARK LIFE SCIENCES LTD, as CONSUlTANT, Retired from GLENMARK in Jan2022 Research Centre as Principal Scientist, Process Research (bulk actives) at Mahape, Navi Mumbai, India. Total Industry exp 32 plus yrs, Prior to joining Glenmark, he has worked with major multinationals like Hoechst Marion Roussel, now Sanofi, Searle India Ltd, now RPG lifesciences, etc. He has worked with notable scientists like Dr K Nagarajan, Dr Ralph Stapel, Prof S Seshadri, etc, He did custom synthesis for major multinationals in his career like BASF, Novartis, Sanofi, etc., He has worked in Discovery, Natural products, Bulk drugs, Generics, Intermediates, Fine chemicals, Neutraceuticals, GMP, Scaleups, etc, he is now helping millions, has 9 million plus hits on Google on all Organic chemistry websites. His friends call him Open superstar worlddrugtracker. His New Drug Approvals, Green Chemistry International, All about drugs, Eurekamoments, Organic spectroscopy international, etc in organic chemistry are some most read blogs He has hands on experience in initiation and developing novel routes for drug molecules and implementation them on commercial scale over a 32 PLUS year tenure till date Feb 2023, Around 35 plus products in his career. He has good knowledge of IPM, GMP, Regulatory aspects, he has several International patents published worldwide . He has good proficiency in Technology transfer, Spectroscopy, Stereochemistry, Synthesis, Polymorphism etc., He suffered a paralytic stroke/ Acute Transverse mylitis in Dec 2007 and is 90 %Paralysed, He is bound to a wheelchair, this seems to have injected feul in him to help chemists all around the world, he is more active than before and is pushing boundaries, He has 100 million plus hits on Google, 2.5 lakh plus connections on all networking sites, 100 Lakh plus views on dozen plus blogs, 227 countries, 7 continents, He makes himself available to all, contact him on +91 9323115463, email amcrasto@gmail.com, Twitter, @amcrasto , He lives and will die for his family, 90% paralysis cannot kill his soul., Notably he has 38 lakh plus views on New Drug Approvals Blog in 227 countries......https://newdrugapprovals.wordpress.com/ , He appreciates the help he gets from one and all, Friends, Family, Glenmark, Readers, Wellwishers, Doctors, Drug authorities, His Contacts, Physiotherapist, etc He has total of 32 International and Indian awards

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	shivkr2 on SPSR Excellence Award 2025 – S…
	Bonkasaurus on Infigratinib phosphate
	PALOVAROTENE \| ORGAN… on Palovarotene
	Pfizer just purchase… on Temanogrel
	Pfizer To Cash In On… on Temanogrel
	VÍDEOS – A Pfizer ac… on Temanogrel
	Pfizer Bought Arena… on Temanogrel
	Pfizer va profita de… on Temanogrel
	Pfizer to Cash In on… on Temanogrel
	Pfizer tocmai a achi… on Temanogrel
	Pfizer just purchase… on Temanogrel
	Pfizer just purchase… on Temanogrel
	Tanya A on Dasotraline, ダソトラリン
	Julia Chernus on RIDINILAZOLE
	Adv.Siji Antony Kera… on Myself Anthony Crasto up for g…

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N-{(2S,3R)-4,4-difluoro-1-(2-hydroxy-2-methylpropanoyl)-2-. [(2,3′,5′-trifluoro[1,1′-biphenyl]-3-yl)methyl]pyrrolidin-3-yl}ethanesulfonamide

A) tert-butyl (2S,3R)-3-(ethylsulfonamido)-4,4-difluoro-2-((2,3′,5′-trifluoro-[1,1′-biphenyl]-3-yl)methyl)pyrrolidine-1-carboxylate

B) N-((2S,3R)-4,4-difluoro-2-((2,3′,5′-trifluoro-[1,1′-biphenyl]-3-yl)methyl)pyrrolidin-3-yl)ethanesulfonamide hydrochloride

C) N-{(2S,3R)-4,4-difluoro-1-(2-hydroxy-2-methylpropanoyl)-2-[(2,3′,5′-trifluoro[1,1′-biphenyl]-3-yl)methyl]pyrrolidin-3-yl}ethanesulfonamide

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