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Nedizantrep

July 8, 2026 2:26 am / Leave a comment

Nedizantrep

CAS 2376824-99-4

MF C20H19ClN6O3 MW 426.9 g/mol

1-[[3-[(3R,5R)-5-(4-chlorophenyl)oxolan-3-yl]-1,2,4-oxadiazol-5-yl]methyl]-2,7-dimethylpurin-6-one

1-({3-[(3R,5R)-5-(4-chlorophenyl)oxolan-3-yl]-1,2,4-oxadiazol-5-yl}methyl)-2,7-dimethyl-1,7-dihydro-6Hpurin-6-one
transient receptor potential (TRP) ion channel antagonist, GDC-6599, GDC 6599, RG 6341, RG-6341, ENQ95FVE4X

Nedizantrep (also known by its developmental code GDC-6599) is a potent, selective, and orally active chemical compound developed as a transient receptor potential ankyrin 1 (TRPA1) cation channel antagonist. It was originally designed by Roche Holding AG/Genentech to manage respiratory conditions, particularly chronic cough associated with asthma and Chronic Obstructive Pulmonary Disease (COPD).

Key Characteristics & Mechanism

Target Engagement: It acts as a TRPA1 inhibitor with high potency, exhibiting an IC50 value of 5.3 nM in humans. [1, 2]
Therapeutic Purpose: It blocks TRPA1 cation channels, which are thermoTRP channels known to function as sensor transducers for temperature, pain, and environmental irritants. Inhibiting this pathway prevents the sensory nerve hypersensitivity that triggers chronic coughing fits.
Research Status: As per data recorded by platforms like the IUPHAR/BPS Guide to PHARMACOLOGY, its chemical structure was publically disclosed in late 2023, and it has been evaluated through Phase 2 clinical trials
A Study To Evaluate The Efficacy, Safety, Pharmacokinetics, And Pharmacodynamic Effects Of GDC-6599 In Patients With Chronic Cough
CTID: NCT05660850
Phase: Phase 2
Status: Completed
Date: 2025-12-16

PAT

US10710994,

https://patentscope.wipo.int/search/en/detail.jsf?docId=US251637879&_cid=P12-MRBG82-53830-1

Example 8: 1-((3-((3R,5R)-5-(4-chlorophenyl)tetrahydrofuran-3-yl)-1,2,4-oxadiazol-5-yl)methyl)-2,7-dimethyl-1H-purin-6(7H)-one

The overall Example 8 reaction scheme is as follows:

Step 4: Preparation of 1-((3-((3R,5R)-5-(4-chlorophenyl)tetrahydrofuran-3-yl)-1,2,4-oxadiazol-5-yl)methyl)-2,7-dimethyl-1H-purin-6(7H)-one

5-(chloromethyl)-3-[(3R,5R)-5-(4-chlorophenyl)tetrahydrofuran-3-yl]-1,2,4-oxadiazole (8.40 g, 28.1 mmol, prepared according to a similar procedure as example 1), 2,7-dimethyl-1H-purin-6(7H)-one (5.07 g, 30.9 mmol) and potassium carbonate (11.6 g, 84.2 mmol) were charged in a 200 mL RBF. DMF (56 mL) was added and the mixture was stirred in a 40° C. oil bath for 2 hours. Heat was removed and the reaction mixture was transferred to a separatory funnel containing EtOAc (100 mL) and water (500 mL). The mixture was extracted with EtOAc (3×100 mL). The combined organic layers were washed with a mixture of water (40 mL) and brine (40 mL), dried over anhydrous Na ₂SO ₄, filtered and concentrated under reduced pressure to give the crude product (77% purity by LCMS). The crude brown oil was dissolved in EtOAc (100 mL) and Heptane (60 mL) was added dropwise which led to the slow formation of a solid. The mixture was stirred at 0° C. for 30 min. and the solid was collected on a Büchner funnel, rinsed with heptane and air dried for 15 min. to give a first lot of 1-((3-((3R,5R)-5-(4-chlorophenyl)tetrahydrofuran-3-yl)-1,2,4-oxadiazol-5-yl)methyl)-2,7-dimethyl-1H-purin-6(7H)-one (8.0 g, 18.7 mmol, 67% yield, 92% purity by LCMS) as a yellow solid. The filtrate was concentrated and it was purified by reverse phase chromatography (C18, MeCN/10 mM NH ₄HCO ₂in H ₂O, pH 3.8, 0 to 60% gradient) to afford a second lot of 1-((3-((3R,5R)-5-(4-chlorophenyl)tetrahydrofuran-3-yl)-1,2,4-oxadiazol-5-yl)methyl)-2,7-dimethyl-1H-purin-6(7H)-one (950 mg, 2.23 mmol, 8% yield, >99% purity by LCMS) as a white solid.

The first lot of desired product (8.0 g, 92% purity by LCMS) was combined with a third lot obtained from a previous batch (1.3 g, 96% purity by LCMS). The material was dissolved in EtOAc (250 mL) and the solvent was displaced with iPrOH on the rotavap (3 cycles of iPrOH addition (50 mL)/evaporation of 50 mL of solvent). During the process, a solid crashed out and the solvent was reduced to ˜100 mL on the rotavap. The suspension was cooled to 0° C. and the solid was collected on a Büchner funnel, rinsed with cold iPrOH and air dried for 15 min. to give a fourth lot of 1-((3-((3R,5R)-5-(4-chlorophenyl)tetrahydrofuran-3-yl)-1,2,4-oxadiazol-5-yl)methyl)-2,7-dimethyl-1H-purin-6(7H)-one (8.50 g, 99% purity by LCMS) as a light beige solid. Still not satisfied with the color of the purified material, it was dissolved in EtOAc (500 mL) and the brown solution was treated with 8 g of activated charcoal. The mixture was allowed to stir for 15 min. The suspension was filtered on celite and the cake was rinsed with EtOAc. The colorless filtrate was evaporated under reduced pressure to give a fifth lot of 1-((3-((3R,5R)-5-(4-chlorophenyl)tetrahydrofuran-3-yl)-1,2,4-oxadiazol-5-yl)methyl)-2,7-dimethyl-1H-purin-6(7H)-one (7.50 g, 99% purity by LCMS) as a white solid. Finally, the second lot (950 mg, >99% purity by LCMS) and the fifth lot (7.50 g, 99% purity by LCMS) were combined in a 200 mL RBF and iPrOH (100 mL) was added. The suspension was stirred in a 100° C. oil bath until full dissolution and water was added (3 mL). The flask was removed from oil bath and the light yellow clear solution was allowed to cool down at room temperature. The suspension was cooled in an ice bath and the solid was collected on a Buchner funnel, rinsed with cold iPrOH (20 mL) and air dried for 24 hours to give the title compound 1-((3-((3R,5R)-5-(4-chlorophenyl)tetrahydrofuran-3-yl)-1,2,4-oxadiazol-5-yl)methyl)-2,7-dimethyl-1H-purin-6(7H)-one (7.3 g) as a white solid. LCMS: purity=99.4%, MH ⁺=427.2/429.2. ¹H NMR (400 MHz, DMSO-d6) δ 8.18 (s, 1H), 7.46-7.33 (m, 4H), 5.63 (s, 2H), 5.00 (t, J=7.4 Hz, 1H), 4.35 (dd, J=8.4, 7.5 Hz, 1H), 3.93 (s, 3H), 3.95-3.88 (m, 1H), 3.79-3.70 (m, 1H), 2.60 (s, 3H), 2.63-2.53 (m, 1H), 2.13 (ddd, J=12.7, 8.9, 7.8 Hz, 1H).

PAT

[WO2019182925A1]

EG 8

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References

Oxadiazole compounds as transient receptor potential channel inhibitors

Publication Number: EP-3768260-B1

Priority Date: 2018-03-19

Grant Date: 2025-10-08

Oxadiazole transient receptor potential channel inhibitorsPublication Number: TW-202003510-APriority Date: 2018-03-19
Oxadiazole transient receptor potential channel inhibitorsPublication Number: US-10710994-B2Priority Date: 2018-03-19Grant Date: 2020-07-14
Oxadiazole transient receptor potential channel inhibitorsPublication Number: TW-I829676-BPriority Date: 2018-03-19Grant Date: 2024-01-21
Oxadiazole transient receptor potential channel inhibitorsPublication Number: US-2025122184-A1Priority Date: 2018-03-19
Oxadiazole transient receptor potential channel inhibitorsPublication Number: EP-3768260-A1Priority Date: 2018-03-19
Oxadiazole transient receptor potential channel inhibitorsPublication Number: US-2019284179-A1Priority Date: 2018-03-19
Oxadiazole transient receptor potential channel inhibitorsPublication Number: KR-20230070333-APriority Date: 2018-03-19
Oxadiazole transient receptor potential channel inhibitorsPublication Number: US-12202824-B2Priority Date: 2018-03-19Grant Date: 2025-01-21
Oxadiazole transient receptor potential channel inhibitorPublication Number: KR-102533094-B1Priority Date: 2018-03-19Grant Date: 2023-05-16
Oxadiazole transient receptor potential channel inhibitorsPublication Number: TW-202438496-APriority Date: 2018-03-19
Oxadiazole transient receptor potential channel inhibitorsPublication Number: US-2020308161-A1Priority Date: 2018-03-19
Oxadiazole transient receptor potential channel inhibitorsPublication Number: US-2023121700-A1Priority Date: 2018-03-19
Oxadiazole transient receptor potential channel inhibitorsPublication Number: WO-2019182925-A1Priority Date: 2018-03-19
Oxadiazole transient receptor potential channel inhibitorsPublication Number: US-11655245-B2Priority Date: 2018-03-19Grant Date: 2023-05-23
Oxadiazole transient receptor potential channel inhibitorsPublication Number: CN-111867585-APriority Date: 2018-03-19

////////////nedizantrep, anax labs, transient receptor potential (TRP) ion channel antagonist, GDC-6599, GDC 6599, RG 6341, RG-6341, ENQ95FVE4X

Navlimetostat

July 5, 2026 2:44 am / Leave a comment

Navlimetostat

CAS 2630904-45-7

ALSO 2630904-44-6

MF C23H18ClFN6O2 MW464.9 g/mol

(2M)-2-{4-[4-(aminomethyl)-1-oxo-1,2-dihydrophthalazin-6-yl] -1-methyl-1H-pyrazol-5-yl}-4-chloro-6-(cyclopropyloxy)-3-fluorobenzonitrile
antineoplastic, MRTX-1719, BMS-986504, MRTX 1719, BMS 986504

Navlimetostat (also known as MRTX-1719 or BMS-986504) is an investigational, first-in-class oral targeted cancer therapy being developed by Bristol-Myers Squibb. It works by selectively binding to the PRMT5-MTA complex, exploiting synthetic lethality to kill cancer cells with MTAP gene deletions while sparing healthy cells.

Navlimetostat is currently in Phase 1/2 clinical trials for advanced solid tumors, including MTAP-deficient non-small cell lung cancer (NSCLC), pancreatic cancer, and glioblastoma.

Key highlights and ongoing research:

Mechanism: In MTAP-deleted cancer cells, a metabolite called MTA accumulates and binds to PRMT5. Navlimetostat targets and inhibits this specific PRMT5-MTA complex, leading to tumor cell death.
Clinical Trials: It is currently being investigated as a monotherapy (e.g., in MTAP-deleted advanced solid tumors) and in combination with other agents like pumitamig

OriginatorMirati Therapeutics
DeveloperBristol-Myers Squibb; Mirati Therapeutics
ClassAntineoplastics; Small molecules
Mechanism of ActionPRMT5 protein inhibitors
Phase II/IIIAdenocarcinoma; Non-small cell lung cancer
Phase I/IIMesothelioma; Neurilemmoma; Pancreatic cancer; Solid tumours
22 May 2026University of Southampton in collaboration with Bristol-Myers Squibb plans a phase II SELECTmeso1 trial for Malignant mesothelioma (Second-line therapy or greater) in United Kingdom in May 2026 (PO, Tablet) (NCT07602946)
13 May 2026Northwestern University plans a phase Ib/II trial for Solid tumours (Metastatic disease, Second-line therapy or greater, Combination therapy) in USA(PO) in December 2027 (NCT07594626)
12 May 2026M.D. Anderson Cancer Center plans a phase I/II trial for Non-small cell lung cancer (Combination therapy, Late-stage disease, Metastatic disease, Second-line therapy or greater) in USA (PO), in November 2026 (NCT07579221)

PRMT5 Inhibitor BMS-986504 is an orally bioavailable methylthioadenosine (MTA)-selective inhibitor of the protein arginine methyltransferase 5 (PRMT5), with potential antineoplastic activity. Upon oral administration, PRMT5 inhibitor BMS-986504 targets, binds to and inhibits PRMT5 that is bound to MTA, a complex that is elevated in methylthioadenosine phosphorylase (MTAP)-deleted cancer cells, thereby specifically inhibiting the function of PRMT5 solely within MTAP-deleted cancer cells and not in normal, healthy cells. By inhibiting the methyltransferase activity of PRMT5, levels of both monomethylated and dimethylated arginine residues in histones H2A, H3 and H4 are decreased. This modulates the expression of genes involved in several cellular processes, including cellular proliferation. This may increase the expression of antiproliferative genes and/or decrease the expression of genes that promote cell proliferation, which may lead to decreased growth of rapidly proliferating cancer cells. BMS-986504 also causes dysregulated RNA splicing and decreased retinoblastoma protein (pRb). Together, this decreases proliferation and increases apoptosis specifically in MTAP-deleted cancer cells. PRMT5, a type II methyltransferase that catalyzes the formation of both omega-N monomethylarginine (MMA) and symmetric dimethylarginine (sDMA) on histones and a variety of other protein substrates involved in signal transduction and cellular transcription, is essential for the viability of cancer and normal cells. It is overexpressed in several neoplasms. Elevated levels are associated with decreased patient survival. MTAP is deleted in certain cancer cells leading to an accumulation of the metabolite MTA; MTA binds to and partially inhibits the activity of PRMT5.

PAT

https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2021050915&_cid=P12-MR76CL-04796-1

[0186] Step 6: To a solution of 6-bromo-4-(chloromethyl)-2H-phthalazin-1-one 13c (148 g, crude) in DMF (1.5 L) was added (1,3-dioxoisoindolin-2-yl)potassium (121 g, 653 mmol). The reaction mixture was stirred at 90 °C for 2 hours and then cooled to 25 °C. The formed precipitate was filtered and washed with DMF (200 mL x 2) and the filter cake triturated with water (1.00 L), filtered and dried to give Intermediate F, 2-[(7-bromo-4-oxo-3H-phthalazin-1-yl)methyl]isoindoline-1,3-dione (162 g, 413 mmol, 76% yield) as a white solid.¹H NMR (400 MHz, DMSO-d₆) d = 12.59 (s, 1H), 8.43 (d, J = 1.2 Hz, 1H), 8.18 (d, J = 8.4 Hz, 1H), 8.07 (dd, J = 1.6, 8.4 Hz, 1H), 7.97 – 7.93 (m, 2H), 7.92 – 7.86 (m, 2H), 5.19 (s, 2H). LCMS [M+1]: 383.9.

[0327] Step 4: A mixture of 4-chloro-6-(cyclopropoxy)-3-fluoro-2-(2-methylpyrazol-3-yl)benzonitrile (180 mg, 0.617 mmol, 1.00 eq) and N-bromosuccinimide (220 mg, 1.23 mmol, 2.00 eq.) in acetonitrile (10 mL) was stirred at 40 °C for 2 hours under a nitrogen atmosphere. After such time the mixture was concentrated and the residue was purified by prep-TLC (SiO₂, petroleum ether: ethyl acetate 20%) to give 2-(4-bromo-2-methyl-pyrazol-3-yl)-4-chloro-6-(cyclopropoxy)-3-fluoro-benzonitrile (170 mg, 0.455 mmol, 74% yield) as a white solid. LCMS [M+1] ⁺ = 371.8; ¹H NMR (400 MHz, CDCl₃) d = 7.61 (s, 1H), 7.55 (d, J = 6.0 Hz, 1H), 3.93 – 3.85 (m, 1H), 3.80 (s, 4H), 0.97 – 0.94 (m, 4H).

EXAMPLE 16-7 and 16-8

[0590] Example 4-230, 2-(4-(4-(aminomethyl)-1-oxo-1,2-dihydrophthalazin-6-yl)-1-methyl-1H-pyrazol-5-yl)-4-chloro-6-cyclopropoxy-3-fluorobenzonitrile (30 mg, 0.065 mmol) separated by SFC (DAICEL CHIRALPAK IC (250 mm × 30 mm x 10 mm); mobile phase:

[0.1% NH₃H₂O isopropanol]; B%: 40% isocratic, 4.1 min cycle; 120 min total ) to give example 16-7 (ee > 99%, 13 mg, 0.026 mmol, 25% yield) as a yellow solid and example 16-8 (8 mg, ee = 84% ). Example 16-8 was then then further separated by SFC (DAICEL CHIRALPAK IC (250 mm × 30 mm,10 mm); mobile phase: [0.1% NH₃H₂O EtOH]; B%: 60% isocratic, 3.1 min cycle; total 50 min) to give Example 16-8 (ee > 99%, 4 mg, 0.007 mmol, 7% yield) as a yellow gum. Spectra data for Example 16-7: LCMS [M+1] ⁺ = 465.1; ¹H NMR (400 MHz, DMSO-d₆) d = 12.59 – 12.44 (s, 1H), 8.29 (s, 1H), 8.15 (d, J = 8.4 Hz, 1H), 8.01 (d, J = 6.0 Hz, 1H), 7.75 (s, 1H), 7.67 (br d, J = 7.6 Hz, 1H), 4.23 – 4.17 (m, 1H), 3.86 (br s, 2H), 3.78 (s, 3H), 0.94 – 0.88 (m, 2H), 0.84 – 0.79 (m, 2H). Spectra data for Example 16-8: LCMS [M+1] ⁺ = 465.1; ¹H NMR (400 MHz, DMSO-d₆) d = 12.49 – 12.37 (s, 1H), 8.26 (s, 1H), 8.15 (d, J = 8.4 Hz, 1H), 8.00 (d, J = 6.0 Hz, 1H), 7.73 (d, J = 1.6 Hz, 1H), 7.72 – 7.68 (m, 1H), 4.19 (m, 1H), 3.80 (s, 2H), 3.77 (s, 3H), 0.93 – 0.87 (m, 2H), 0.83 – 0.78 (m, 2H).

PAT

MTA-synergistic PRMT5 inhibitorsPublication Number: CN-114728912-APriority Date: 2019-09-12
Mta-cooperative prmt5 inhibitorsPublication Number: WO-2021050915-A1Priority Date: 2019-09-12
MTA-Cooperative PRMT5 InhibitorsPublication Number: US-2021078994-A1Priority Date: 2019-09-12
MTA-Cooperative PRMT5 InhibitorsPublication Number: US-2021079003-A1Priority Date: 2019-09-12

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References

Dynamic Kinetic Resolution of Axially Chiral MRTX1719Publication Name: SynfactsPublication Date: 2022-10-18DOI: 10.1055/s-0041-1738738
Design and evaluation of achiral, non-atropisomeric 4-(aminomethyl)phthalazin-1(2H)-one derivatives as novel PRMT5/MTA inhibitorsPublication Name: Bioorganic & Medicinal ChemistryPublication Date: 2022-10-01PMID: 35926325DOI: 10.1016/j.bmc.2022.116947
Synthesis of MRTX1719Publication Name: SynfactsPublication Date: 2022-03-18DOI: 10.1055/s-0041-1737934
Fragment-Based Discovery of MRTX1719, a Synthetic Lethal Inhibitor of the PRMT5•MTA Complex for the Treatment of MTAP -Deleted CancersPublication Name: Journal of Medicinal ChemistryPublication Date: 2022-01-18PMID: 35041419DOI: 10.1021/acs.jmedchem.1c01900
Disordered methionine metabolism in MTAP/CDKN2A-deleted cancers leads to dependence on PRMT5Publication Name: Science (New York, N.Y.)Publication Date: 2016-03-11PMID: 26912361DOI: 10.1126/science.aad5944
Synthesis of MRTX1719DOI: 10.1055/s-0041-1737934Publication Date: 2022Publication Name: Synfacts
Dynamic Kinetic Resolution of Axially Chiral MRTX1719DOI: 10.1055/s-0041-1738738Publication Date: 2022Publication Name: Synfacts

////////navlimetostat, anax labs, antineoplastic, MRTX-1719, BMS-986504, MRTX 1719, BMS 986504

Moxetomidate

July 4, 2026 2:32 am / Leave a comment

Moxetomidate

CAS 1567838-90-7

MF C15H18N2O3 MW 274.31 g/mol

2-methoxyethyl 3-[(1R)-1-phenylethyl]imidazole-4-carboxylate

2-methoxyethyl 1-[(1R)-1-phenylethyl]-1H-imidazole-5-carboxylate
GABAA receptor agonist, hypnotic, ET-26, ET 26, LPQ2K767W2

Moxetomidate (also known as methoxyetomidate or ET-26) is a novel, investigational short-acting intravenous anesthetic and sedative-hypnotic agent. It functions as a{GABA}_A} receptor agonist and is designed as a “soft drug” analogue of the traditional anesthetic etomidate.

The Purpose of Its Development

Traditional etomidate is highly valued in clinical settings for its exceptional cardiovascular stability, making it the agent of choice for inducing anesthesia in patients with low blood pressure, trauma, or severe heart conditions. However, its primary drawback is that it causes prolonged adrenocortical suppression by inhibiting the enzyme 11β-hydroxylase. This limits its safety for continuous infusions or repeated uses.

Moxetomidate was synthesized to overcome this exact limitation. It retains the favorable, heart-safe properties of etomidate while undergoing rapid metabolic breakdown into an inactive compound. This prevents prolonged suppression of the adrenal gland.

Key Scientific Properties

Mechanism of Action: It acts as a positive allosteric modulator and agonist at the \(GABA}_A}) receptor site, depressing the central nervous system to induce hypnosis and sedation.
Chemical Profile: Its chemical formula is C₁₅H₁₈N₂O₃ with a molecular weight of 274.31 g/mol. Its IUPAC name is 2-methoxyethyl (R)-1-(1-phenylethyl)-1H-imidazole-5-carboxylate.
Clinical Trial Status: Developed by entities including Jinzhou Ahon Pharmaceutical Co., Ltd., moxetomidate hydrochloride (ET-26 HCl) has progressed into Phase 3 clinical trials as an induction anesthetic.

Methoxyetomidate is an investigational anesthetic agent being developed by Jinzhou Ahon Pharmaceutical Co., Ltd. It is a short-acting intravenous anesthetic that acts as a positive allosteric modulator of GABAA receptors.^[1][2] As of 2024, methoxyetomidate is undergoing Phase 3 clinical trials for use in anesthesia.^[3][1]

PAT

https://patentscope.wipo.int/search/en/detail.jsf;jsessionid=D2B4BB918D25AFB75D4682C639A62719.wapp2nB?docId=US189917922&_cid=P21-MR5QSJ-95402-1

EG 1

Preparation of the Formula (I) Compound Guided by the Present Invention

The compound of Formula (II) (CAS: 56649-48-0) (216 mg, 1 mmol), the compound of Formula (III) (CAS: 6482-24-2) (278 mg, 2 mmol), and anhydrous potassium carbonate (564 mg, 3 mmol) were mixed and added in 15 mL of N,N-dimethylformamide, and the mixture was stirred at 50° C. and reacted overnight. Next day, the reaction solution was poured into 100 mL of cold water to obtain a clear solution, and was then extracted with ethyl acetate for three times (50 mL for each time). The combined organic layer was dried with anhydrous sodium sulfate and filtered to give the filtrate. Evaporation of the solvent under the reduced pressure provided oily crude products. After purification by silica gel column (eluent: cyclohexane/ethyl acetate=3/2), colorless oily product (150 mg) was obtained, with a yield of 54%.

1) NMR: apparatus: Bruker, internal standard substance: TMS

¹H-NMR (400 MHz CDCl ₃) δ: 1.862 (3H, d, J=7.2 Hz), 3.393 (3H, s), 3.645 (3H, t, J=4.8 Hz), 4.31˜4.405 (2H, m), 6.348 (1H, q, J=7.2 Hz), 7.17˜7.359 (m, 5H), 7.742 (s, 1H), 7.827 (s, 1H).

¹³C-NMR (100 MHz CDCl ₃) δ: 22.30, 55.48, 59.15, 63.53, 70.48, 122.39, 126.36, 128.08, 128.93, 138.63, 140.02, 141.20, 160.26.

2) MS: mass spectrometer: API3000 LC-Ms/Ms from American ABI company; ionization mode: ESI.

(M+H).HRMS: for C ₁₅H ₁₈N ₂O ₃+H, calcd 275.1396, found 275.1396.

3) Optical rotation value: The ethanol solution of the compound of Formula (I) was prepared at a concentration of 1 g/100 mL, and [α]D ²⁰value was measured using Polarimeter 341 polarimeter, with [α] _D ²⁰=+71.9°.

4) The ee value: The compound of Formula (I) was dissolved in methanol at a concentration of 1 mg/mL and then diluted 100 times before injection. The detection was performed by HPLC using chiral AD column, wavelength of UV detector: 254 nm, mobile phase: 20% isopropanol-n-hexane, flow rate: 1 mL/min. The optical purity of the compound of Formula (I) was determined to be 100% ( FIG. 1).

PAT

N-substituted imidazole carboxylic ester chiral compound containing an ether side chain, its preparation and applicationPublication Number: US-9969695-B2Priority Date: 2013-12-23Grant Date: 2018-05-15
N-substituted imidazole carboxylic ester chiral compound containing ether side chain, preparation method and applicationPublication Number: EP-3088394-A1Priority Date: 2013-12-23
N-Substituted Imidazole Carboxylic Ester Chiral Compound Containing an Ether Side Chain, Its Preparation and ApplicationPublication Number: US-2017001963-A1Priority Date: 2013-12-23
N-substituted imidazole carboxylic ester chiral compound containing ether side chain, preparation method and applicationPublication Number: WO-2015096551-A1Priority Date: 2013-12-23

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References

“ET-26 Methoxyetomidate Hydrochloride Development Information”. Synapse by Patsnap. Retrieved 2024-11-23.
Wang B, Chen S, Yang J, Yang L, Liu J, Zhang W (2017). “ET-26 hydrochloride (ET-26 HCl) has similar hemodynamic stability to that of etomidate in normal and uncontrolled hemorrhagic shock (UHS) rats”. PLOS ONE. 12 (8) e0183439. Bibcode:2017PLoSO..1283439W. doi:10.1371/journal.pone.0183439. PMC 5557577. PMID 28813523.
“ET-26 Clinical Trials Overview”. Synapse by Patsnap. Retrieved 2024-11-23.


Clinical data
Other names	ET-26; Moxetomidate
Identifiers
IUPAC name
CAS Number	1567838-90-7
PubChem CID	74766803
ChemSpider	133326476
UNII	LPQ2K767W2
Chemical and physical data
Formula	C₁₅H₁₈N₂O₃
Molar mass	274.320 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES
InChI

//////////moxetomidate, anax labs, GABAA receptor agonist, hypnotic, ET-26, ET 26, LPQ2K767W2

Mirivadelgat

July 2, 2026 2:46 am / Leave a comment

Mirivadelgat

CAS 1804941-96-5

MF C30H34FN3O5 MW535.6 g/mol

L-Valine, [2-[4-(cyclopropylmethoxy)-3-[[[(3-fluoro-4-methoxyphenyl)methyl]amino]carbonyl]phenyl]-3-pyridinyl]methyl ester

[2-[4-(cyclopropylmethoxy)-3-[(3-fluoro-4-methoxyphenyl)methylcarbamoyl]phenyl]-3-pyridinyl]methyl (2S)-2-amino-3-methylbutanoate

L-Valine, [2-[4-(cyclopropylmethoxy)-3-[[[(3-fluoro-4-methoxyphenyl)methyl]amino]carbonyl]phenyl]-3-pyridinyl]methyl ester

{2-[4-(cyclopropylmethoxy)-3-{[(3-fluoro-4-methoxyphenyl)methyl]carbamoyl}phenyl]pyridin-3-yl}methyl
L-valinate
aldehyde dehydrogenase 2 activator, antianaemic, FP 045, 22TB7Q431D

Mirivadelgat (also known as FP-045) is a first-in-class, orally bioavailable small molecule that acts as a selective activator of mitochondrial aldehyde dehydrogenase 2 (ALDH2). Developed by Foresee Pharmaceuticals, this novel therapy helps cells clear toxic reactive aldehydes, reducing mitochondrial stress, cellular inflammation, and fibrosis. It is currently being evaluated in clinical trials for its disease-modifying potential across several serious conditions.

Current Clinical Development

The drug is undergoing clinical evaluation for multiple indications:

Pulmonary Hypertension with Interstitial Lung Disease (PH-ILD): Mirivadelgat is currently in a multinational, Phase 2 trial known as the WINDWARD Study. The double-blind trial is assessing whether the drug can safely improve pulmonary vascular resistance and overall lung and cardiac function.
Parkinson’s Disease: The drug was selected for the SLEIPNIR multi-drug Phase 2a platform trial funded by Cure Parkinson’s. It will evaluate mirivadelgat’s safety, brain penetration, and ability to clear the toxic waste products that drive Parkinson’s progression.
Fanconi’s Anaemia: It has also reached Phase I/II testing for this rare genetic condition.
Other Conditions: Early-stage Phase I research has explored its utility for metabolic and kidney disorders.

Mechanism of Action

When administered once daily, mirivadelgat targets deep cellular mechanics:

ALDH2 Activation: It binds selectively to the ALDH2 enzyme in the mitochondria.
Waste Clearance: It accelerates the metabolism of toxic reactive aldehydes produced by oxidative stress.
Mitochondrial Protection: Lowering toxic aldehyde levels protects cellular structures and shields tissues from fibrosis and dysfunction.

Mirivadelgat is an orally bioavailable selective activator of the mitochondrial isoform of aldehyde dehydrogenase (ALDH2), with potential protective activity. Upon oral administration, mirivadelgat increases ALDH2 activity. This increases the metabolism of toxic reactive aldehydes and lowers the level of the toxic aldehydes. This may protect cells from the toxic aldehydes and prevent mitochondria diseases and disorders. ALDH2, a mitochondrial regulator of toxic aldehyde metabolism, plays an important role in the metabolism of toxic aldehydes. Toxic aldehydes are produced by oxidative stress.

Study to Evaluate Safety and Efficacy of Mirivadelgat in PH-ILD

CTID: NCT06475781, Phase: Phase 2, Status: Recruiting, Date: 2025-10-06

OriginatorForesee Pharmaceuticals
ClassAntianaemics; Antihypertensives; Cardiovascular therapies; Hepatoprotectants; Small molecules
Mechanism of ActionAldehyde dehydrogenase 2 stimulants
Phase IIPulmonary hypertension
Phase I/IIFanconi’s anaemia
Phase IKidney disorders; Metabolic disorders
No development reportedCardiovascular disorders; Non-alcoholic fatty liver disease; Non-alcoholic steatohepatitis
08 Jun 2026Foresee Pharmaceuticals in collaboration with Haukeland University Hospital plans a phase IIa SLEIPNIR Platform trial for Parkinson’s disease (PO)
02 Jun 2026Helse Bergen HF, Cure Parkinson’s, Norwegian Parkinson’s Association plan the phase IIa SLEIPNIR-2 trial for Parkinson’s disease in Norway (PO, Capsule), in September 2026 , (CTIS2025-523570-17-00)
28 Oct 2025No recent reports of development identified for phase-I development in Cardiovascular-disorders in USA (PO)

PAT

https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2015127137&_cid=P20-MR2WCE-70172-1

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References

Mitochondrial aldehyde dehydrogenase-2 binding compounds and methods of use thereofPublication Number: US-9879036-B2Priority Date: 2014-02-19Grant Date: 2018-01-30
Mitochondrial aldehyde dehydrogenase-2 binding compounds and methods of use thereofPublication Number: US-2017057982-A1Priority Date: 2014-02-19
Mitochondrial aldehyde dehydrogenase 2 (aldh2) binding polycyclic amides and their use for the treatment of cancerPublication Number: EP-3107899-B1Priority Date: 2014-02-19Grant Date: 2020-08-12

//////////mirivadelgat, anax labs, aldehyde dehydrogenase 2 activator, antianaemic, FP 045, 22TB7Q431D

Milpecitinib

July 1, 2026 2:43 am / Leave a comment

Milpecitinib

CAS 1415819-54-3

MF C20H20N4O2S MW380.5 g/mol

N-[3-[4-[5-(pyrrolidine-1-carbonyl)-1H-pyrrol-3-yl]-1,3-thiazol-2-yl]phenyl]acetamide

N-(3-{4-[5-(pyrrolidine-1-carbonyl)-1H-pyrrol-3-yl]-1,3-thiazol-2-yl}phenyl)acetamide
Janus tyrosine kinase inhibitor, anti-inflammatory, veterinary, PF-06263276, PF 06263276, Ph 1012, DNX 04013, CPh 1012, Ph-1012, CVXL 0074-02, 4Q8TT4B4GN

Milpecitinib is a small molecule drug. Milpecitinib has a monoisotopic molecular weight of 380.13 Da.

Milpecitinib (also known by its developmental codes PF-06263276, Ph-1012, and DNX-04013) is a potent, small-molecule Janus kinase (JAK) inhibitor used primarily in veterinary medicine and laboratory research. It functions as an ATP-competitive, broad-spectrum (pan-JAK) inhibitor that targets all four members of the JAK family: JAK1, JAK2, JAK3, and Tyrosine Kinase 2 (TYK2).

Primary Indication and Target

Veterinary Use: Milpecitinib is designated for the control of pruritus (itching) associated with canine allergic dermatitis and the management of canine atopic dermatitis (CAD).
Sponsorship: The United States Adopted Name (USAN) for this drug was officially adopted following sponsorship by Phibro Animal Health.
Research Use: In laboratory settings, it is utilized to study complex inflammatory pathways, immune disorders, and certain cancers.

Mechanism of Action

Milpecitinib works by blocking the ATP-binding site of JAK enzymes. This inhibition halts the JAK-STAT signaling pathway, which plays a critical role in cellular responses to inflammatory cytokines. By blocking this cascade, the drug prevents the production and signaling of pro-inflammatory cytokines that cause severe itching and skin inflammation in dogs.

SYN

https://patentscope.wipo.int/search/en/detail.jsf;jsessionid=5D288DBBA230B78048641EFCD848FF01.wapp1nA?docId=US76372787&_cid=P10-MR1GR5-42689-1

A solution of acetyl chloride in DCM was added dropwise to a mixture of aniline and triethylamine in DCM under cooling on ice bath. Partial dissolution was observed followed by white precipitation. The solid was collected by filtration, washed with water and dried over vacuum yielding white powder (0.128 g 22%). HPLC—100% purity. LCMS—(ES ⁺) Calcd. 380.13. Found 381.1 (MH ⁺).

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Can’t Find? Let’s Connect

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References

Compositions and methods for modulating kinasesPublication Number: JP-6054379-B2Priority Date: 2011-06-07Grant Date: 2016-12-27
Compositions and methods for modulating a kinasePublication Number: EP-2718290-B1Priority Date: 2011-06-07Grant Date: 2016-05-04
Compositions and methods for modulating a kinasePublication Number: CA-2837268-CPriority Date: 2011-06-07Grant Date: 2020-05-12
Compositions and Methods for Modulating a KinasePublication Number: US-2012316148-A1Priority Date: 2011-06-07
Compositions and methods for modulating a kinasePublication Number: EP-2718290-A2Priority Date: 2011-06-07
Compositions and methods for modulating a kinasePublication Number: WO-2012172438-A9Priority Date: 2011-06-07
Compositions and methods for modulating a kinasePublication Number: US-8937065-B2Priority Date: 2011-06-07Grant Date: 2015-01-20
Compositions and methods for modulating kinasesPublication Number: JP-2014520108-APriority Date: 2011-06-07
Compositions and methods for modulating a kinasePublication Number: WO-2012172438-A2Priority Date: 2011-06-07
Compositions and methods to modulate a kinasePublication Number: ES-2585244-T3Priority Date: 2011-06-07Grant Date: 2016-10-04
Compound for modulating a kinase
Publication Number: BR-112013031121-B1
Priority Date: 2011-06-07

//////////milpecitinib, anax labs, Janus tyrosine kinase inhibitor, anti-inflammatory, veterinary, PF-06263276, PF 06263276, Ph 1012, DNX 04013, CPh 1012, Ph-1012, CVXL 0074-02, 4Q8TT4B4GN

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