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Simedeutirom

September 20, 2026 2:33 am / Leave a comment

Simedeutirom

CAS 2403721-24-2

MF C18H92H3Cl2N6O4 MW 450.25

2-[3,5-Dichloro-4-[[(7R)-2,5,6,7-tetrahydro-7-(methyl-d3)-1-oxo-1H-cyclopenta[d]pyridazin-4-yl]oxy]phenyl]-2,3,4,5-tetrahydro-3,5-dioxo-1,2,4-triazine-6-carbonitrile

2-[3,5-dichloro-4-[[(7R)-1-oxo-7-(trideuteriomethyl)-2,5,6,7-tetrahydrocyclopenta[d]pyridazin-4-yl]oxy]phenyl]-3,5-dioxo-1,2,4-triazine-6-carbonitrile

2-(3,5-dichloro-4-{[(7R)-7-(2H3)methyl-1-oxo-2,5,6,7-tetrahydro-1Hcyclopenta[d]pyridazin-4-yl]oxy}phenyl)-3,5-dioxo-2,3,4,5-tetrahydro-1,2,4-triazine-6-carbonitrile
thyroid hormone beta receptor agonist, 4G7Z7KQ8GV

Simedeutirom is a selective, synthetic, deuterium-labeled thyroid hormone receptor beta (THR-β) agonist. It features a novel cyclopenta $d$ 𝑑pyridazine core and is primarily utilized as a specialized tool compound in the biochemical research of metabolic diseases, including obesity, type 2 diabetes mellitus, and related metabolic disorders.

Core Structural & Pharmacological Profile

Target Selectivity: It functions as a potent agonist specifically targeting the thyroid hormone receptor beta (THR-β), with an half-maximal effective concentration (EC₅₀) ranging between 0.1 to 1 μM. THR-β activation plays a foundational role in modulating hepatic lipid metabolism, lowering cholesterol, and regulating overall energy expenditure without heavily triggering the alpha receptor (THR-α), which is associated with adverse cardiac side effects.
Deuterium Labeling: The compound incorporates deuterium (a stable isotope of hydrogen) into its chemical architecture, specifically modified as a trideuteriomethyl group. Isotopic modification or “deuteration” is an established medicinal chemistry approach frequently evaluated to slow metabolic clearance and increase structural stability.
Chemical Identifiers:
- Molecular Formula: C₁₈H₁₂Cl₂N₆O₄
- Molecular Weight: 450.25 g/mol
- CAS Registry Number: 2403721-24-2
- FDA UNII Code: 4G7Z7KQ8GV

Research Context & Status

Simedeutirom is categorized under the International Nonproprietary Name (INN) database. However, it is fundamentally classified for in vitro and in vivo research use only. It has not been approved for clinical therapeutic use or direct distribution to patients.

PAT

WO 2019240938

https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2019240938&_cid=P11-MU978W-22170-1

PAT

US20250179050

https://patentscope.wipo.int/search/en/detail.jsf;jsessionid=B04410250978C4E0B0F323AD027AC8B8.wapp1nB?docId=US457344867&_cid=P11-MU96YW-11754-1

Example 1 Preparation of crude free base of compound I

Step 1: preparation of compound b

N-(3,5-dichloro-4-((7-(methyl-d3)-1-oxo-2,5,6,7-tetrahydro-1H-cyclopenta [d]pyridazin-4-yl)oxy)phenyl)benzamid

4.62 kg of compound a was completely dissolved in 25.0 L of glacial acetic acid and added to a 100 L reaction kettle, 3300 g of benzoic anhydride was added, and the mixture was reacted at room temperature for about 4 hours with stirring turned on. The reaction was monitored by TLC (n-hexane/ethyl acetate=5/1) until compound a disappeared, then 2722 g of anhydrous sodium acetate was additionally added and the temperature was increased to 120° C. for a reaction under stirring for about 18 hours.

The reaction solution was cooled to 60-65° C., and concentrated under reduced pressure to remove most of the acetic acid. After the concentration was completed, 10 L of anhydrous ethanol was added to the residue and uniformly mixed. Then the mixed solution was slowly added to 250 L of water, while maintaining the rapid stirring, and a large amount of solid precipitated during the addition, and stirring was continued for about 0.5 hours after the addition, followed by centrifugation. The filter cake was washed with purified water (20 L×2) to give compound b in 100% yield, which went directly to the next step.

1H NMR (400 MHZ, DMSO) δ 12.07 (s, 1H), 10.55 (s, 1H), 8.04 (s, 2H), 7.98-7.95 (m, 2H), 7.63-7.50 (m, 3H), 3.29-3.25 (m, 1H), 3.02-2.90 (m, 2H), 2.39-2.36 (m, 1H), 1.75-1.72 (m, 1H).

LCMS m/z=433.1 [M+1]+

Step 2: preparation of compound c

4-(4-amino-2,6-dichlorophenoxy)-7-(methyl-d3)-2,5,6,7-tetrahydro-1H-cyclopenta [d]pyridazin-1-on

To a 100 L reaction kettle, 5.76 kg of the crude compound b from the previous step, a potassium hydroxide solution (2606 g KOH dissolved in 19.5 L of purified water) and 6.0 L of anhydrous ethanol were added under stirring. After the complete addition, the mixture was heated to reflux and reacted for about 16 hours, and the raw material was controlled for a complete reaction.

The temperature was reduced to 25° C., 30 L of water was added, the pH was adjusted to 8-9 with an ammonium chloride solid, and 35.0 L of ethyl acetate was added and stirred. The solution was phase-separated. The aqueous phase was extracted with ethyl acetate (15.0 L×2). The organic phases were combined and washed with a 5% aqueous sodium chloride solution (25 L×2). The organic phase was dried over 3.0 Kg of anhydrous sodium sulfate, filtered, and concentrated until no significant distillate flowed out, so as to obtain a crude product.

The crude product and 7.0 L of an aqueous 10% dioxane solution were heated for complete dissolution, cooled to room temperature, and crystallized with stirring for about 16 hours, followed by filtration to obtain a wet product, which was repeated purified twice and dried under vacuum at 50° C. for about 12 hours to give 1507 g of compound c.

1H NMR (400 MHZ, DMSO) δ 11.98 (s, 1H), 6.67 (m, 2H), 5.60 (s, 2H), 3.30-3.19 (m, 1H), 3.03-2.93 (m, 1H), 2.90-2.70 (m, 1H), 2.35 (m, 1H), 1.69 (m, 1H).

LCMS m/z=329.0 [M+1]+

Step 3: preparation of compound d

(R)-4-(4-amino-2,6-dichlorophenoxy)-7-(methyl-d3)-2,5,6,7-tetrahydro-1H-cyclopenta [d]pyridazin-1-one

3298 g of racemate c was subjected to chiral resolution to give, two optical isomers from separation:

Compound d (retention time: 1.583 min, 1230 g, off-white solid, ee %=99.60%, yield 37.3%); and compound d-1 (retention time: 1.926 min, 1255 g, off-white solid, ee %=99.76%, yield 38.1%).

Resolution conditions:

Instrument: MG III preparative SFC; column: Whelk 01 (S, S), 300× 50 mm I.D., 10 um; mobile phase: A: CO2, B: methanol; gradient: B 40%; flow rate: 200 mL/min; back pressure: 100 bar; column temperature: 38° C.; wavelength: 220 nm; period: 4.5 min; sample preparation: the racemate was dissolved in methanol/dichloromethane to achieve 50 mg/ml; and injection: 17 ml/injection.

Compound d

1H NMR (400 MHZ, DMSO) δ 11.98 (s, 1H), 6.67 (s, 2H), 5.60 (s, 2H), 3.30-3.19 (m, 1H), 3.03-2.93 (m, 1H), 2.90-2.70 (m, 1H), 2.35 (dtd,1H), 1.69 (ddt, 1H).

LCMS m/z=329.1 [M+1]+

Compound d-1

1H NMR (400 MHZ, DMSO) δ 11.98 (s, 1H), 6.68 (d, 2H), 5.60 (s, 2H), 3.29-3.18 (m, 1H), 2.97 (tdd, 1H), 2.90-2.72 (m, 1H), 2.35 (dtd, 1H), 1.69 (ddt, 1H).

LCMS m/z=329.0 [M+1]+

Step 4: preparation of compound e

Ethyl(R,Z)-(2-cyano-2-(2-(3,5-dichloro-4-((7-(methyl-d3)-1-oxo-2,5,6,7-tetrahydro-1H-cyclopenta [d]pyridazin-4-yl)oxy)phenyl) hydrazineylidene) acetyl) carbamate

To a 100 L reaction kettle, 16.0 kg of acetic acid, 4.0 kg of purified water and 2.0 kg of compound d were added with stirring. The temperature was reduced to 0+5° C., then 2.36 kg of hydrochloric acid was added, and after the addition, the temperature was maintained at 0+5° C. with stirring for about 20 minutes. A sodium nitrite solution (0.5 kg of sodium nitrite dissolved in 1.0 kg of purified water) was dropwise added with the temperature being controlled at 0+5° C., and after the addition, the temperature was maintained at 0+5° C. for reaction for 2 hours. The temperature was controlled at 5+5° C. and a sodium acetate solution (1.5 kg of sodium acetate dissolved in 6.0 kg of purified water) was added dropwise, then 0.99 kg of N-cyanoacetourethane was added, and then the temperature was increased to 10+5° C. for a reaction for about 2 hours. Then a sample was taken for HPLC monitoring, after which time samples were taken at each about 2-hour interval, and the reaction was not stopped until the content of compound d was determined by HPLC to be≤1.0%.

After the completion of the reaction, the temperature was controlled to 10+5° C., and 30.0 kg of purified water was added to the reaction kettle. After the addition, the temperature was controlled at 10+5° C. with stirring continued for 1 hour, followed by filtration, and the cake was washed with 3.0 kg of purified water. The filter cake and 12.6 kg of anhydrous ethanol were added to a 100 L reaction kettle, heated to 50±5° C., and stirred for about 1 hour. The mixture was cooled to 20±5° C., stirred for 0.5 hours and filtered, and the filter cake was washed once with 1.26 kg of anhydrous ethanol.

The filter cake was dried at 55+5° C. with vacuum≤−0.07 MPa for about 17 hours, and compound e was obtained and collected, weighing 2.6327 kg.

1H NMR (400 MHZ, DMSO) δ 12.08 (d, 2H), 10.88 (s, 1H), 7.99 (s, 2H), 4.21 (q, 2H), 3.30-3.17 (m, 1H), 3.08-2.95 (m, 1H), 2.95-2.80 (m, 1H), 2.38 (ddd, 1H), 1.78-1.63 (m, 1H), 1.28 (t, 3H).

LCMS m/z=496.1 [M+1]+

Step 5: preparation of compound of formula I

(R)-2-(3,5-dichloro-4-((7-(methyl-d3)-1-oxo-2,5,6,7-tetrahydro-1H-cyclopenta [d]pyridazin-4-yl)oxy)phenyl)-3,5-dioxo-2,3,4,5-tetrahydro-1,2,4-triazine-6-carbonitrile

To a 100 L reaction kettle, 12.40 kg of N,N-dimethylacetamide, 2.6269 kg of compound e and 0.54 kg of sodium acetate were added with stirring. After the addition, the temperature was increased and the internal temperature was maintained at 115+5° C. for a reaction for about 2 hours. Then a sample was taken for HPLC monitoring, after which time samples were taken at each about 2-hour interval, and the reaction was not stopped until the content of compound e was determined by HPLC to be≤1.0%.

After the completion of the reaction, the temperature was reduced to 60±5° C., 0.788 kg of purified water was added to the reaction solution, and after the addition, the reaction solution was filtered while still hot and quickly added to 13.66 kg of purified water, and the temperature was lowered to 10+5° C. After filtration, the filter cake was added to 20 L of dimethyl sulfoxide and warmed for complete dissolution. 800 L of acetone was added and stirred for 0.5 to 1 h, and then filtered. The filter cake was dried at 55+5° C. with vacuum≤−0.07 MPa for about 20 hours to give the amorphous form of the compound of formula (I), weighing 1.56 kg.

1H NMR (400 MHZ, DMSO) δ 13.26 (s, 1H), 12.09 (s, 1H), 7.79 (s, 2H), 3.32-3.24 (m, 1H), 3.10-2.99 (m, 1H), 2.96-2.88 (m, 1H), 2.45-2.31 (m, 1H), 1.77-1.69 (m, 1H).

LCMS m/z=450.0 [M+1]+.

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References

Method for preparing (r)-1,4-dichloro-5-(methyl-d3)-6,7-dihydro-5h-cyclopenta[d]pyridazinePublication Number:WO-2025055949-A1Priority Date:2023-09-12
Polymorph as thyroid hormone receptor agonists and use thereofPublication Number:WO-2023147752-A1Priority Date:2022-02-07
Preparation method of pyridazinone derivative, and intermediate thereofPublication Number:TW-202342457-APriority Date:2022-02-07
Preparation method of pyridazinone derivative, and intermediate thereofPublication Number:WO-2023147779-A1Priority Date:2022-02-07
Polymorph as thyroid hormone receptor agonists and use thereofPublication Number:EP-4477652-A1Priority Date:2022-02-07

////////simedeutirom, anax labs, thyroid hormone beta receptor agonist, 4G7Z7KQ8GV

#simedeutirom, #anax labs, #thyroid hormone beta receptor agonist, #4G7Z7KQ8GV

Elunetirom

May 13, 2026 2:50 am / Leave a comment

Elunetirom

CAS 2156649-32-8

MF C19H21Cl2NO3 MW382.3 g/mol

2-[3,5-dichloro-4-[(4-hydroxy-3-propan-2-ylphenyl)methyl]phenoxy]-N-methylacetamide

2-(3,5-dichloro-4-{[4-hydroxy-3-(propan-2-yl)phenyl]methyl}phenoxy)-N-methylacetamide
thyroid hormone beta receptor agonist, ABX-002, MA-JD21, ABX 002, MA JD21, QTW4WC4BRX, MA-JD-21,

Elunetirom (ABX-002/MA-JD21) is an oral, brain-penetrant thyroid hormone receptor beta agonist being developed by Autobahn Therapeutics for major depressive disorder (MDD) and bipolar depression. As of early 2026, it is in Phase 2 clinical trials, aiming to treat these disorders with fewer peripheral side effects than traditional treatments.

Key Facts About Elunetirom

Mechanism: It is a prodrug converted into an active metabolite that selectively targets TR$\beta $ in the central nervous system (CNS), boosting brain energy and plasticity.
Development Stage: Currently in Phase 2 trials for major depressive disorder (MDD) and bipolar depression.
Target Indications: Primarily for psychiatric conditions, with preclinical research for neurodegenerative diseases like multiple sclerosis and adrenomyeloneuropathy.
Benefits: Designed to offer a favorable safety profile compared to synthetic thyroid hormones, minimizing systemic side effects.

Clinical Status (2025–2026)
As of early 2026, Autobahn Therapeutics has reported positive Phase 1 data, confirming its, safety, tolerability, and ability to engage with brain targets.

Phase 2 Focus: Evaluating its potential as an add-on (adjunctive) therapy for depression.
Preclinical Findings: Studies suggest it may help repair myelin (remyelination) and treat cognitive impairment.

Elunetirom, also known by its developmental code names ABX-002 and MA-JD21, is a thyroid hormone receptor agonist which is under development for the treatment of major depressive disorder, bipolar depression, multiple sclerosis, and adrenomyeloneuropathy.^[1][2] It is a prodrug of LL-340001 and acts as a potent, selective, and centrally penetrant agonist of the thyroid hormone receptor beta (TRβ).^[1][2] The drug produces psychoplastogenic effects similar to those of brain-derived neurotrophic factor (BDNF) in rodents.^[2] In addition, it has been found to improve cognitive impairment caused by old age or scopolamine treatment in rodents.^[2] Eunetirom is under development by Autobahn Therapeutics.^[1] As of December 2025, it is in phase 2 clinical trials for treatment of major depressive disorder and bipolar depression and is in the preclinical research stage of development for multiple sclerosis and adrenomyeloneuropathy.^[1]

SYN

[WO2022236133A1]

https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2022236133&_cid=P21-MP3GH3-29154-1

PAT

https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2017201320&_cid=P21-MP3GLZ-35721-1

xample 16. Preparation of 2-(3. 5-dichloro-4-(4-hvdroxy-3-isopropylbenzyl) phenoxy)-N-methylacetamide (MA-JD21; 10b)

0142] 2-(3, 5-dichloro-4-(4-hydroxy-3-isopropylbenzyl) phenoxy) acetic acid (100 mg, 0.27 mmol, 1 equiv.) was dissolved in methanol (5 mL) in a sealed tube. Sulfuric acid (1 drop) added to it and the reaction was sealed and heated to 65°C for one hour while stirring. It was cooled to room temperature and TLC analysis (ethyl acetate: hexane 1 : 1) shows complete conversion to the intermediate methyl ester. To this was then added 40% methyl amine in water (320μ1, 4mmol, 15 equiv.). The reaction is resealed and heated to 65°C for one hour. The reaction flask was cooled to room temperature and sodium hydroxide (0.5N, 10 mL) added to it. The reaction product was extracted with dichoromethane (3 x 50 mL). The organic layers were combined, dried on anhydrous Mg₂S0₄, filtered and concentrated. Purification by flash chromatography (50% hexane in ethylacetate) gave the product as a white solid (65 mg, 0.17 mmol, 63%). ^XH NMR (400 MHz, MeOH-c¾): 5=7.12 (s, 2H), 7.01 (d, IH, J=1.98Hz), 6.77 (dd, IH, J=8.21Hz, 2.26Hz), 6.62 (d, IH, J=8.21Hz), 4.56 (s, 2H), 4.15 (s, 2H), 3.23 (septet, IH, J=7.14Hz), 2.85 (s, 3H), 1.17 (d, 6H, J= 6.93Hz). HRMS exact mass calculated for C1₉H21CI2NO₃ [M + H] ⁺: m/z 384.09455, found m/z 384.09473.

PAT

Derivatives of sobetiromePublication Number: US-10870616-B2Priority Date: 2016-05-18Grant Date: 2020-12-22
Process for the preparation of derivatives of sobetiromePublication Number: EP-3936497-A1Priority Date: 2016-05-18
Subiterol DerivativesPublication Number: CN-113277958-APriority Date: 2016-05-18
Sobetarom derivativePublication Number: JP-6982004-B2Priority Date: 2016-05-18Grant Date: 2021-12-17
Derivatives of sobetiromePublication Number: US-2019210950-A1Priority Date: 2016-05-18
History of SubtirumPublication Number: IL-263050-APriority Date: 2016-05-18
Derivatives of sorbetyromPublication Number: KR-102331596-B1Priority Date: 2016-05-18Grant Date: 2021-11-25
Derivatives of sobetiromePublication Number: EP-3457851-B1Priority Date: 2016-05-18Grant Date: 2021-06-23
Fatty acid amide hydrolase (faah) cleavable prodrugs of thyromimetics and combination with peripherally restricted faah inhibitorsPublication Number: EP-4333844-A1Priority Date: 2021-05-06
Isotopic thyromimetic compoundsPublication Number: US-2023348364-A1Priority Date: 2020-06-03
Sobetarom derivativePublication Number: JP-2022033788-APriority Date: 2016-05-18
Derivatives of sobetiromePublication Number: AU-2017267734-A1Priority Date: 2016-05-18
Derivatives of sobetiromePublication Number: WO-2017201320-A1Priority Date: 2016-05-18
Fatty acid amide hydrolase (faah) cleavable prodrugs of thyromimetics and combination with peripherally restricted faah inhibitorsPublication Number: US-2024254075-A1Priority Date: 2021-05-06
Fatty acid amide hydrolase (FAAH) cleaves prodrugs of thyroxine drugs and combinations with peripherally restricted FAAH inhibitorsPublication Number: CN-117597122-APriority Date: 2021-05-06
Fatty acid amide hydrolase (faah) cleavable prodrugs of thyromimetics and combination with peripherally restricted faah inhibitorsPublication Number: WO-2022236133-A1Priority Date: 2021-05-06
Fatty acid amide hydrolase (faah) cleavable prodrugs of thyromimetics and combination with peripherally restricted faah inhibitorsPublication Number: AU-2022271304-A1Priority Date: 2021-05-06
Fatty acid amide hydrolase (faah) cleavable prodrugs of thyromimetics and combination with peripherally restricted faah inhibitorsPublication Number: CA-3217789-A1Priority Date: 2021-05-06

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WEBSITE https://www.anaxlab.com/

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Development Solutions, Developing from Lab scale to PR&D, Kilo Scale-ups and Commercial Scales

SEE MORE………Integrated Solutions, Manufacturing Solutions, Products,
Can’t Find? Let’s Connect

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References

“Autobahn Therapeutics”. AdisInsight. 2 December 2025. Retrieved 7 January 2026.
Harris J, Baccei J, Franey B, Vivian JA, MacKenna D, Stratton W, et al. (January 2026). “ACNP 64th Annual Meeting: Poster Abstracts P584-P872”. Neuropsychopharmacology. 51 (Suppl 1). Nature Publishing Group: 410–571. doi:10.1038/s41386-025-02281-2. PMID 41507446.

Clinical data

Other names	ABX-002; ABX002; MA-JD21; MA-JD-21
Routes of administration	Oral^[1]
Drug class	Thyromimetic; Thyroid hormone receptor beta (TRβ) agonist
Identifiers
IUPAC name
CAS Number	2156649-32-8
PubChem CID	132160637
DrugBank	DB18157
ChemSpider	129433137
UNII	QTW4WC4BRX
KEGG	D13273
ChEMBL	ChEMBL5314909
Chemical and physical data
Formula	C₁₉H₂₁Cl₂NO₃
Molar mass	382.28 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES
InChI

///////////elunetirom, ANAX LABS, thyroid hormone beta receptor agonist, ABX-002, MA-JD21, ABX 002, MA JD21, QTW4WC4BRX, MA-JD-21,

#elunetirom, #ANAX LABS, #thyroid hormone beta receptor agonist, #ABX-002, #MA-JD21, #ABX 002, #MA JD21, #QTW4WC4BRX, #MA-JD-21,

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Step 1: preparation of compound b

N-(3,5-dichloro-4-((7-(methyl-d3)-1-oxo-2,5,6,7-tetrahydro-1H-cyclopenta [d]pyridazin-4-yl)oxy)phenyl)benzamid

Step 2: preparation of compound c

4-(4-amino-2,6-dichlorophenoxy)-7-(methyl-d3)-2,5,6,7-tetrahydro-1H-cyclopenta [d]pyridazin-1-on

Step 3: preparation of compound d

(R)-4-(4-amino-2,6-dichlorophenoxy)-7-(methyl-d3)-2,5,6,7-tetrahydro-1H-cyclopenta [d]pyridazin-1-one

Compound d

Compound d-1

Step 4: preparation of compound e

Ethyl(R,Z)-(2-cyano-2-(2-(3,5-dichloro-4-((7-(methyl-d3)-1-oxo-2,5,6,7-tetrahydro-1H-cyclopenta [d]pyridazin-4-yl)oxy)phenyl) hydrazineylidene) acetyl) carbamate

Step 5: preparation of compound of formula I

(R)-2-(3,5-dichloro-4-((7-(methyl-d3)-1-oxo-2,5,6,7-tetrahydro-1H-cyclopenta [d]pyridazin-4-yl)oxy)phenyl)-3,5-dioxo-2,3,4,5-tetrahydro-1,2,4-triazine-6-carbonitrile

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