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Ontunisertib
Ontunisertib
CAS 2647949-48-0
MFC27H21F2N5O MW469.5 g/mol
- 1H-Pyrazole-1-acetamide, N-[(2,6-difluorophenyl)methyl]-3-(6-methyl-2-pyridinyl)-4-(4-quinolinyl)-
- N-(2,6-Difluorobenzyl)-2-(3-(6-methylpyridin-2-yl)-4-(quinolin-4-yl)-1H-pyrazol-1-yl)acetamide
N-[(2,6-difluorophenyl)methyl]-2-[3-(6-methyl-2-pyridinyl)-4-quinolin-4-ylpyrazol-1-yl]acetamide
N-(2,6-difluorobenzyl)-2-(3-(6-methylpyridin-2-yl)-4-(quinolin-4-yl)-1H-pyrazol-1-yl)acetamide
N-[(2,6-difluorophenyl)methyl]-2-[3-(6-methylpyridin-2-yl)-4-(quinolin-4-yl)-1H-pyrazol-1-yl]acetamide
serine/threonine kinase inhibitor, AGMB 129, SF6HGC94LK
Ontunisertib (AGMB-129) is an experimental, orally active small-molecule drug developed by Agomab Therapeutics to treat Fibrostenosing Crohn’s Disease (FSCD). It acts as a highly selective inhibitor of ALK5 (also known as Transforming Growth Factor-beta type I receptor or TGF-β RI).
Mechanism of Action
- Local Targeting: Designed to act specifically within the gastrointestinal (GI) tract.
- High Tissue Exposure: Provides high local exposure in inflamed and scarred intestinal tissues.
- Liver Inactivation: Undergoes rapid first-pass metabolism in the liver immediately after GI absorption.
- Safety Feature: Converts into an inactive metabolite to prevent systemic exposure and avoid cardiac toxicity.
Clinical Development Status
- FDA Status: Granted Fast Track Designation by the U.S. FDA.
- Phase 2a Results: Successfully completed the STENOVA clinical trial. Results demonstrated excellent safety, high local tissue penetration, and positive structural improvements in bowel strictures.
- Phase 2b Trial: Enrolling patients for the global, 52-week NOV-ERA trial to test multiple doses against a placebo. The primary goal is assessing the endoscopically confirmed widening of narrowed intestinal strictures
- NOV-ERA – A Clinical Trial to Assess the Efficacy and Safety of Ontunisertib Compared to Placebo in Patients With Fibrostenosing Crohn’s DiseaseCTID: NCT07683325Phase: Phase 2Status: Not yet recruitingDate: 2026-07-06
- Human Mass Balance Study of [14C] Ontunisertib in Healthy VolunteersCTID: NCT07672574Phase: Phase 1Status: Not yet recruitingDate: 2026-06-29
- A Multiple Ascending Dose Study With AGMB-129 in Healthy ParticipantsCTID: NCT07118878Phase: Phase 1Status: CompletedDate: 2025-11-21
- STENOVA – A Study to Evaluate Safety, Tolerability, PK and PD of AGMB-129 in Patients With Fibrostenotic Crohn’s DiseaseCTID: NCT05843578Phase: Phase 2Status: Active, not recruitingDate: 2025-11-21
- Drug-Drug Interaction Study With AGMB-129 and Midazolam in Healthy ParticipantsCTID: NCT05937386Phase: Phase 1Status: CompletedDate: 2024-06-18
SYN
SYN
https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2021105317&_cid=P20-MRPQUQ-14721-1
Example 24: N-(2,6-difluorobenzyl)-2-(3-(6-methylpyridin-2-yl)-4-(quinolin-4-yl)-1H-pyrazol-1 -yl)acetamide
1H-NMR (300 MHz, DMSO-d6): δ = 8.84 (d, J = 4.4 Hz, 1H), 8.76 (t, J = 5.3 Hz, 1H), 8.11-7.97 (m, 2H), 7.75-7.28 (m, 7H), 7.13 (t, J = 7.8 Hz, 2H), 6.97 (d, J = 7.5 Hz, 1 H), 4.99 (s, 2H), 4.43 (d, J = 5.3 Hz, 2H), 1.83 (s, 3H).
HPLC-MS: Rt 17.513 m/z 470.0 [M+H]+.
PAT
https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2025176835&_cid=P20-MRPR39-19345-1
Potent inhibitors of TGFpRII-TGFpRI (ALK5) have been described in W02021/105317 including the compound (/V-(2,6-difluorobenzyl)-2-(3-(6-methylpyridin-2-yl)-4-(quinolin-4-yl)-1/7-pyrazol-1-yl)acetamide) which is the compound of formula (I) as shown below (see Example 24):
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References
///////////ontunisertib, anax labs, serine/threonine kinase inhibitor, AGMB 129, SF6HGC94LK
Olisutrigine bromide
Olisutrigine bromide
Cas 1393836-45-7
MF C25H35BrN2 MW443.5 g/mol
N-[2-[(2R)-1,1-dimethylpiperidin-1-ium-2-yl]ethyl]-N-(2-methylphenyl)-2,3-dihydro-1H-inden-2-amine bromide
(2R)-2-{2-[N-(2,3-dihydro-1H-inden-2-yl)-2-methylanilino]ethyl}-1,1-dimethylpiperidin-1-ium bromide
sodium channel blocker, analgesic, ASN008, ASN 008, EN 3427, 0M9Q318030
Olisutrigine bromide (also known as ASN-008 or EN3427) is an investigational, permanently charged sodium channel blocker being studied for its potent, long-lasting analgesic (pain-relieving) properties.
Key Characteristics
- Mechanism of Action: It acts as a membrane-impermeant sodium channel blocker. Because it carries a permanent cationic charge, it cannot easily cross healthy cell membranes on its own.
- Targeted Delivery: It often requires a “vehicle” or a combination drug (like lidocaine) to activate specific channels (such as TRP channels), allowing olisutrigine entry into pain-sensing neurons where it becomes entrapped and blocks pain signaling.
- Efficacy: Rodent pain models demonstrate that its analgesic effects are significantly longer-lasting than lidocaine alone.
- Chemical Profile: Its molecular formula is C₂₅H₃₅BrN₂ with a molecular weight of 443.5 g/mol, and its CAS registry number is 1393836-45-7.
Current Status
- Investigational Drug: It is not approved for human or veterinary medical use and remains in the research and development phase.
- Availability: It is strictly available as a reference standard compound for laboratory and preclinical research through chemical suppliers like MedChemExpress and BenchChem.
A Study to Evaluate the Anti-pruritic Effectiveness of ASN008 in Adults With Mild to Moderate Atopic Dermatitis
CTID: NCT05870865
Phase: Phase 2
Status: Completed
Date: 2025-05-16
SYN
https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2012112969&_cid=P11-MRILQZ-81481-1
Example 43: General Procedure M – Preparation of (R)-1,1 -dimethyl-2-[2-((indan-2-yl)(2-methylphenyl)amino)ethyl]piperidinium bromide
Alcohol 37b was synthesized as previouslydescribed (Tetrahedron 2007, 63, 3000-3005)
To a 250 mL round bottom flask was charged 2-(2-hydroxyethyl)piperidine-1-carboxylic acid tert-butyl ester 37b (5.0 g, 21.80 mmol), dichloromethane (7.50 mL), a solution of KBr (0.52 g, 4.36 mmol) in 2.0 mL of water and TEMPO (0.1 g, 0.64 mmol). The mixture was cooled to about -5 °C. A solution of NaOCl (31.1 mL, 5.25%, 24.1 mmol) was added slowly over 20 minutes while maintaining the temperature at 0 °C. The mixture was further stirred at 0°C for 20 minutes. The organic layer was separated, and the aqueous layer was extracted with
dichloromethane. The combined dichloromethane extract was washed with water (50 mL), followed by brine. After drying over MgSO4, the mixture was filtered and concentrated. The crude was purified with silica gel column chromatography to give product 38b (4.1 g, 83%) as colorless oil.
O
To a clean and dry 250 mL round bottom flask was charged sodium triacetoxyborohydride (5.59 g, 26.40 mmol), 4 A molecular sieves (10.0 g), amine 7e (7.37 g, 33.00 mmol) and dichloromethane (20.0 mL). The mixture was stirred and cooled to about 0 °C, and a solution of aldehyde 38b (5.0 g, 22.00 mmol) in 40 mL of dichloromethane was added. The mixture was then stirred further at 0 °C for about 1 hour and at ambient temperature for an additional 40 minutes. The reaction mixture was quenched with aqueous saturated NaHCO3 (100 mL). After separation of organic layer, the mixture was extracted with dichloromethane. After drying over MgSO4, the organic layer was concentrated. The crude product was purified by silica gel column chromatography to give product 40f (7.2 g, 75.3%) as colorless oil.
To a clean and dry 250 mL round bottom flask was charged lithium aluminum hydride (1.53 g, 40.27 mmol) and THF (30.0 mL). The mixture was heated to reflux. A solution of carbamate 40f (7.0 g, 16.11 mmol) in THF (40.0 mL) was added dropwise over 5 minutes. After refluxing for 15 h, the reaction mixture was cooled to 0 °C, and water (1.55 mL) was added slowly and carefully, followed by THF (100 mL) and 15% NaOH (1.55 mL). After stirring the mixture at room temperature for 1.0 h, MgSO4 was added, and the mixture was stirred further for 15 minutes. The mixture was filtered and concentrated to obtain the crude product, which was purified by silica gel column chromatography to afford product 11e (4.7 g, 84%) as pale yellow oil. Optical purity by chiral HPLC: 99.3% ee.
To a clean and dry 250 mL round bottom flask was charged diamine 11e (4.70 g, 13.49 mmol) and 1.07 M bromomethane in MTBE (126.0 mL, 134.8 mmol). After stirring at room temperature for 20 h, the reaction mixture was filtered. The solid cake was washed with MTBE to give the product (4.40 g, 73%) as white powder. Optical purity by chiral HPLC: 99.3% ee.
PAT
PAT
https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2025250498&_cid=P11-MRILME-78328-1
Compound 1 is described in WO2012/112969, wherein Compound 1 is reported at Example 43, and certain formulations of Compound 1 are described in WO2020/113050,
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References
AMINOINDANE COMPOUNDS AND THEIR APPLICATION FOR THE TREATMENT OF PAIN
Publication Number: RU-2013142433-A
Priority Date: 2011-02-18
- Aminoindane compounds and use thereof in treating painPublication Number: US-8865741-B2Priority Date: 2011-02-18Grant Date: 2014-10-21
- Aminoindan compound and its use in treating painPublication Number: CN-107540599-BPriority Date: 2011-02-18Grant Date: 2021-06-04
- Aminoindane compounds and their use in the treatment of painPublication Number: ES-2675510-T3Priority Date: 2011-02-18Grant Date: 2018-07-11
- Aminoindane compounds and use thereof in treating painPublication Number: EP-2675787-B1Priority Date: 2011-02-18Grant Date: 2018-03-28
- AMINOINDANE COMPOUNDS AND THEIR APPLICATION FOR THE TREATMENT OF PAINPublication Number: RU-2016151688-APriority Date: 2011-02-18
- Aminoindane compounds and use thereof in treating painPublication Number: RU-2612959-C2Priority Date: 2011-02-18Grant Date: 2017-03-14
- AMINOINDAN COMPOUNDS AND USE THEREOF IN THE TREATMENT OF PAINPublication Number: DK-2675787-T3Priority Date: 2011-02-18Grant Date: 2018-07-16
- Load Aminoinden Compounds and Therapeutic Compounds Containing Them and Uses in the Treatment of Itching and PainPublication Number: IL-227967-APriority Date: 2011-02-18
- Aminoindane compounds and use thereof in treating painPublication Number: EP-3363437-B1Priority Date: 2011-02-18Grant Date: 2021-07-28
- Aminoindane compounds and use thereof in treating painPublication Number: KR-20200125765-APriority Date: 2011-02-18
- Aminoindane compounds and use thereof in treating painPublication Number: WO-2012112969-A1Priority Date: 2011-02-18
- Aminoindane compounds and use thereof in treating painPublication Number: CA-2826648-CPriority Date: 2011-02-18Grant Date: 2019-06-04
- Aminoindane compounds for use in treating urological painPublication Number: EP-3970723-A1Priority Date: 2011-02-18
- Aminoindane compounds and use thereof in treating painPublication Number: CA-2826648-A1Priority Date: 2011-02-18
- Aminoindane Compounds and Use Thereof in Treating PainPublication Number: US-2012214809-A1Priority Date: 2011-02-18
- Use of aminoindane compounds in treating overactive bladder and interstitial cystitisPublication Number: US-9044482-B2Priority Date: 2012-08-15Grant Date: 2015-06-02
- Aminoindane compounds and their use in the treatment of painPublication Number: ES-2898910-T3Priority Date: 2011-02-18Grant Date: 2022-03-09
- Aminoindane compounds and use thereof in treating painPublication Number: AU-2012219254-A1Priority Date: 2011-02-18
- Aminoindane compounds and use thereof in treating painPublication Number: EP-2675787-A1Priority Date: 2011-02-18
- Aminoindane compounds and use thereof in treating painPublication Number: EP-3363437-A1Priority Date: 2011-02-18
- 6-(4-Nitro-phenoxy)-2H-pyridazin-3-one and 6-(4-amino-phenoxy)-2H-pyridazin-3-one as intermediates of thyroid hormone analogs The preparation method of ketone derivativePublication Number: CN-116406356-APriority Date: 2020-10-23
- Use of Aminoindane Compounds in Treating Overactive Bladder and Interstitial CystitisPublication Number: US-2014051702-A1Priority Date: 2012-08-15
- Use of aminoindane compounds in treating overactive bladder and interstitial cystitisPublication Number: US-2015290182-A1Priority Date: 2012-08-15
- Use of aminoindane compounds in treating overactive bladder and interstitial cystitisPublication Number: US-9375423-B2Priority Date: 2012-08-15Grant Date: 2016-06-28
- Use of aminoindane compounds in treating overactive bladder and interstitial cystitisPublication Number: WO-2014028675-A1Priority Date: 2012-08-15
///////////olisutrigine bromide, anax labs, sodium channel blocker, analgesic, ASN008, ASN 008, EN 3427, 0M9Q318030
Netanasvir
Netanasvir
CAS 2007900-70-9
MF C51H58N8O7 MW895.1 g/mol
methyl N-[(1R)-2-[(2S,4S)-2-[5-[7-[2-[(2S,5S)-1-[(2S)-2-(methoxycarbonylamino)-3-methylbutanoyl]-5-methylpyrrolidin-2-yl]-3H-benzo[e]benzimidazol-7-yl]-2,3-dihydro-1H-inden-4-yl]-1H-imidazol-2-yl]-4-(methoxymethyl)pyrrolidin-1-yl]-2-oxo-1-phenylethyl]carbamate
- Carbamic acid, N-[(1R)-2-[(2S,4S)-2-[5-[2,3-dihydro-7-[2-[(2S,5S)-1-[(2S)-2-[(methoxycarbonyl)amino]-3-methyl-1-oxobutyl]-5-methyl-2-pyrrolidinyl]-1H-naphth[1,2-d]imidazol-7-yl]-1H-inden-4-yl]-1H-imidazol-2-yl]-4-(methoxymethyl)-1-pyrrolidinyl]-2-oxo-1-phenylethyl]-, methyl ester
- Methyl ((S)-1-((2S,5S)-2-(7-(7-(2-((2S,4S)-1-((R)-2-((methoxycarbonyl)amino)-2-phenylacetyl)-4-(methoxymethyl)pyrrolidin-2-yl)-1H-imidazol-5-yl)-2,3-dihydro-1H-inden-4-yl)-1H-naphtho[1,2-d]imidazol-2-yl)-5-methylpyrrolidin-1-yl)-3-methyl-1-oxobutan-2-yl)carbamate
- methyl {(2S)-1-[(12S,15S,52S,54S,7R)-7-[(methoxycarbonyl)amino]-54-(methoxymethyl)-15-methyl-6-oxo-32,33-dihydro-21H,31H,41H-2(2,7)-naphtho[1,2-d]imidazola-4(4,2)-imidazola-1(2),5(2,1)-dipyrrolidina-3(4,7)-indena-8(1)-benzenaoctaphan-11-yl]-3-methyl-1-oxobutan-2-yl}carbamate
- Methyl N-[(1R)-2-[(2S,4S)-2-[5-[2,3-dihydro-7-[2-[(2S,5S)-1-[(2S)-2-[(methoxycarbonyl)amino]-3-methyl-1-oxobutyl]-5-methyl-2-pyrrolidinyl]-1H-naphth[1,2-d]imidazol-7-yl]-1H-inden-4-yl]-1H-imidazol-2-yl]-4-(methoxymethyl)-1-pyrrolidinyl]-2-oxo-1-phenylethyl]carbamate
antiviral, Dongweizhuo, HCV, Antaitavir Hasophate, HEC 74647 PA, 4Y7YD32BYY
Netanasvir (commonly prescribed as netanasvir phosphate) is a direct-acting antiviral medication primarily used to treat chronic hepatitis C virus (HCV) infection. It was approved by the China National Medical Products Administration (NMPA) under the trade name Dongweizhuo.
Key Clinical Information
- Mechanism of Action: It acts as a potent and selective NS5A inhibitor. By targeting the HCV NS5A protein, it successfully blocks viral RNA replication, virion assembly, and viral clearance mechanisms.
- Combination Therapy: It is exclusively indicated for use in combination with encofosbuvir (an NS5B polymerase inhibitor).
- Target Genotypes: The combination regimen effectively treats adult patients with chronic HCV genotypes 1, 2, 3, or 6.
- Patient Profiles: It is suitable for patients who are either treatment-naïve or have been previously treated with interferon, with or without compensated liver cirrhosis.
- Administration & Elimination: Taken orally, the drug demonstrates high metabolic stability, with feces serving as its primary elimination pathway
- OriginatorSunshine Lake Pharma
- ClassAntivirals
- Mechanism of ActionHepatitis C virus NS 5 protein inhibitors
- RegisteredHepatitis C
- 08 Feb 2025Registered for Hepatitis C (Combination therapy, Treatment-experienced) in China (PO)
- 08 Feb 2025Registered for Hepatitis C (Combination therapy, Treatment-naive) in China (PO)
- 31 Dec 2023NMPA, China accepts NDA for netanasvir for Hepatitis C for review
Netanasvir is an antiviral drug used to treat hepatitis C virus (HCV).[1] In China, netansavir is approved for use in combination with encofosbuvir for the treatment of adult patients with chronic HCV genotypes 1, 2, 3, or 6, who are either treatment-naive or have been previously treated with interferon.[2]
PAT
Compounds as hepatitis c virus inhibitors and pharmaceutical uses thereof
Publication Number: WO-2016141890-A1
Priority Date: 2015-03-12
https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2016141890&_cid=P22-MRH62L-18160-1
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References
- “Netanasvir phosphate – Sunshine Lake Pharma”. Adis Insight. Springer Nature Switzerland AG.
- “Netanasvir Phosphate Capsules Approved for Marketing by China NMPA”. National Medical Products Administration. 2025-06-11.
 | |
| Clinical data | |
|---|---|
| Trade names | 东卫卓; Dongweizhuo |
| Legal status | |
| Legal status | Rx in China |
| Identifiers | |
| IUPAC name | |
| CAS Number | 2007900-70-9 |
| PubChem CID | 122535557 |
| UNII | 4Y7YD32BYY |
| Chemical and physical data | |
| Formula | C51H58N8O7 |
| Molar mass | 895.074 g·mol−1 |
| 3D model (JSmol) | Interactive image |
| SMILES | |
| InChI | |
//////////netanasvir, anax labs, APPROVALS 2025, CHINA 2025, antiviral, Dongweizhuo, HCV, Antaitavir Hasophate, HEC 74647 PA, 4Y7YD32BYY
Nelremagpran
Nelremagpran
CAS 2492595-24-9
MFC15H9ClF4O3 MW 348.67 g/mol
3-[[2-Chloro-4-(trifluoromethyl)phenoxy]methyl]-2-fluorobenzoic acid
3-{[2-chloro-4-(trifluoromethyl)phenoxy]methyl}-2-fluorobenzoic acid
Mas-related G protein-coupled receptor inverse agonist, anti-inflammatory, MRGPRX4 modulator-2, BL83FAK6DZ,
Nelremagpran is an experimental drug that acts as a potent and selective antagonist (or possibly inverse agonist) of the MAS-related Gq protein-coupled receptor X4 (MRGPRX4). It has antiinflammatory effects in animal studies. This receptor is poorly characterised but is thought to be involved in immune system function, and development of selective ligands is essential for researching its role in the body.[1][2]
Nelremagpran is an experimental drug that acts as a potent and selective antagonist or inverse agonist of the Mas-related G-protein-coupled receptor X4 (MRGPRX4). It was initially developed by Escient Pharmaceuticals, Inc. for its anti-inflammatory and anti-itch properties.
🧪 Core Mechanism
The drug targets MRGPRX4, a poorly characterized receptor found in the immune and nervous systems. It functions with high potency, exhibiting an half-maximal inhibitory concentration (IC50) of less than 100 nM.
🔬 Potential Research Applications
Because the receptor plays a significant role in mediating severe itch and pain pathways, Nelremagpran is actively used as a chemical probe to study:
- Chronic Pruritus: Conditions involving persistent, debilitating itch sensations, such as cholestatic pruritus.
- Autoimmune Diseases: Underlying mechanisms in conditions like psoriasis, multiple sclerosis, and Stevens-Johnson Syndrome.
- Inflammatory Sensation: How the body signals pain and immune hypersensitivity
PAT
https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2020198537&_cid=P12-MREAZN-03524-1
Synthesis of Compound 1-55
Step 4-4. Synthesis of methyl 3-(bromomethyl)-2-fluorc>benzoate (INT 4-C)
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#MedicinalChemistry, #DrugDiscovery, #OrganicSynthesis, #ChemicalLibrary, #BuildingBlocks, #SARStudies, #ChemistryInnovation, #medchem, #Drugdevelopment, #Biotech, #Biotechnology, #AnaxLaboratories, #Pharma
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References
 | |
| Identifiers | |
|---|---|
| IUPAC name | |
| CAS Number | 2492595-24-9 |
| PubChem CID | 155145968 |
| ChemSpider | 115008493 |
| UNII | BL83FAK6DZ |
| ChEMBL | ChEMBL4855031 |
| Chemical and physical data | |
| Formula | C15H9ClF4O3 |
| Molar mass | 348.68 g·mol−1 |
| 3D model (JSmol) | Interactive image |
| SMILES | |
| InChI | |
References
- WO 2020/198537, Yeager A, Selfridge B, Sainz M, Martinborough E, Boehm M, Huang, “Modulators of mas-related G-protein receptor x4 and related products and methods.”, published 1 October 2020, assigned to Escient Pharmaceuticals, Inc.
- “International Nonproprietary Names for Pharmaceutical Substances (INN)” (PDF). WHO Drug Information. 38 (4). 2024.
- Modulators of Mas-related G-protein receptor X4 and related products and methodsPublication Number: US-11840521-B2Priority Date: 2019-03-28Grant Date: 2023-12-12
- Modulators of mas-related g-protein receptor x4 and related products and methodsPublication Number: EP-3946304-A1Priority Date: 2019-03-28
- Modulators of mas-related g-protein receptor x4 and related products and methodsPublication Number: US-2023159474-A1Priority Date: 2019-03-28
- Modulators of mas-related g-protein receptor x4 and related products and methodsPublication Number: US-2023053860-A1Priority Date: 2019-03-28
- Modulators of mas-related g-protein receptor x4 and related products and methodsPublication Number: US-2021032213-A1Priority Date: 2019-03-28
- Modulators of mas-related G-protein receptor X4 and related products and methodsPublication Number: US-11643399-B2Priority Date: 2019-03-28Grant Date: 2023-05-09
- Modulators of mas-related g-protein receptor x4 and related products and methodsPublication Number: US-2024300907-A1Priority Date: 2019-03-28
- Modulators of mas-related g-protein receptor x4 and related products and methodsPublication Number: WO-2020198537-A1Priority Date: 2019-03-28
- Modulators of MAS-related G protein receptor X4 and related products and methodsPublication Number: CN-113939288-BPriority Date: 2019-03-28Grant Date: 2025-04-25
//////////nelremagpran, anax labs, Mas-related G protein-coupled receptor inverse agonist, anti-inflammatory, MRGPRX4 modulator-2, BL83FAK6DZ,
Nedizantrep
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)tetrahydro-3-furanyl]-1,2,4-oxadiazol-5-yl]methyl]-1,7-dihydro-2,7-dimethyl-6H-purin-6-one
- 6H-Purin-6-one, 1-[[3-[(3R,5R)-5-(4-chlorophenyl)tetrahydro-3-furanyl]-1,2,4-oxadiazol-5-yl]methyl]-1,7-dihydro-2,7-dimethyl-
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
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
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
PAT
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
Navlimetostat
CAS 2630904-45-7
ALSO 2630904-44-6
MF C23H18ClFN6O2 MW464.9 g/mol
- Benzonitrile, 2-(4-(4-(aminomethyl)-1,2-dihydro-1-oxo-6-phthalazinyl)-1-methyl-1H-pyrazol-5-yl)-4-chloro-6-(cyclopropyloxy)-3-fluoro-, (2S)-
- (M)-27
- 2-[4-[4-(aminomethyl)-1-oxo-2H-phthalazin-6-yl]-2-methylpyrazol-3-yl]-4-chloro-6-cyclopropyloxy-3-fluorobenzonitrile
(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
Moxetomidate
CAS 1567838-90-7
MF C15H18N2O3 MW 274.31 g/mol
- 2-Methoxyethyl 1-[(1R)-1-phenylethyl]-1H-imidazole-5-carboxylate
- 1H-Imidazole-5-carboxylic acid, 1-[(1R)-1-phenylethyl]-, 2-methoxyethyl ester
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
EG 1
Preparation of the Formula (I) Compound Guided by the Present Invention
| 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. |
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
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
Mirivadelgat
CAS 1804941-96-5
MF C30H34FN3O5 MW535.6 g/mol
[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
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
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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
Mazisotine
Mazisotine
CAS 1638588-92-7
MF C16H23N3O2 MW 289.37 g/mol
(1S,5R)-N-[2-methyl-1-[(3-methyl-2-pyridinyl)oxy]propan-2-yl]-3-azabicyclo[3.1.0]hexane-6-carboxamide
rac-(1R,5S,6R)-N-{2-methyl-1-[(3-methylpyridin-2-yl)oxy]propan-2-yl}-3-azabicyclo[3.1.0]hexane-6-carboxamide
(1R,5S,6r)-N-{2-methyl-1-[(3-methylpyridin-2-yl)oxy]propan-2-yl}-3-azabicyclo[3.1.0]hexane-6-carboxamide
somatostatin receptor receptor agonist, LY3556050, CNTX-0290, LY 3556050, CNTX 0290, D3M32WP3MH
Mazisotine (also known as LY3556050 or CNTX-0290) is an experimental, non-opioid chemical compound designed to treat chronic and neuropathic pain. It functions as a selective somatostatin receptor 4 (SSTR4) agonist, meaning it activates specific peripheral nerve pathways to block pain signals without activating the central nervous system’s opioid receptors.
While it showed early promise in animal models, Eli Lilly and Company removed mazisotine from its clinical development pipeline after disappointing results in Phase II clinical trials. It currently remains in use strictly as a chemical tool for laboratory pain research.
Key Facts and Clinical History
- Mechanism of Action: It binds to and activates SSTR4. This triggers a cellular response that suppresses pain and inflammation in peripheral sensory neurons.
- Intended Indications: It was being evaluated to treat diabetic peripheral neuropathic pain, osteoarthritis pain, and chronic low back pain.
- Development Partners: The compound was originally licensed by Eli Lilly from Centrexion Therapeutics in 2019 for an upfront fee of $47.5 million.
- Discontinuation: In mid-2025, Eli Lilly officially dropped the drug. Phase II clinical trials revealed that its efficacy did not meet the high success thresholds required to continue human testing.
- Side Effects: In clinical studies, reported treatment-emergent adverse effects were generally mild to moderate. They included constipation, nausea, dizziness, fatigue, and headaches.
Mazisotine (LY3556050, CNTX-0290) is a chemical compound which acts as an agonist at somatostatin receptor 4. It has analgesic effects and has been researched for the treatment of pain associated with arthritis and neuropathic pain. It was not pursued for human medical use following disappointing results in Phase II clinical trials, but continues to be used in research into the role of SST4 receptors in pain perception.[1][2]
- A Study of LY3556050 in Adult Participants With Diabetic Peripheral Neuropathic PainCTID: NCT06074562Phase: Phase 2Status: CompletedDate: 2025-07-03
- Chronic Pain Master Protocol (CPMP): A Study of LY3556050 in Participants With OsteoarthritisCTID: NCT04627038Phase: Phase 2Status: CompletedDate: 2023-11-02
- Chronic Pain Master Protocol (CPMP): A Study of LY3556050 in Participants With Diabetic Peripheral Neuropathic PainCTID: NCT04707157Phase: Phase 2Status: TerminatedDate: 2023-11-02
- Chronic Pain Master Protocol (CPMP): A Study of LY3556050 in Participants With Chronic Low Back PainCTID: NCT04874636Phase: Phase 2Status: CompletedDate: 2023-11-02
- A Study of Effect of LY3556050 on Metformin in Healthy ParticipantsCTID: NCT05615467Phase: Phase 1Status: CompletedDate: 2023-01-18
- A Study of Single and Repeated Doses of LY3556050 in Healthy ParticipantsCTID: NCT05341102Phase: Phase 1Status: CompletedDate: 2022-04-22
- A Study of LY3556050 in Healthy ParticipantsCTID: NCT04156750Phase: Phase 1Status: CompletedDate: 2020-08-19
PAT
https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2025096300&_cid=P12-MQYLW5-94119-1
SYN
https://patentscope.wipo.int/search/en/detail.jsf?docId=US214328185&_cid=P12-MQYLW3-94084-1
PAT
reparation 1
[0081] Methyl (E)-4-((4-methylphenyl)sulfonamido)but-2-enoate
[0082] Methyl 4-bromobut-2-enoate (36.29g, 202.7mmol) was dissolved in MeCN (500 mL) at 15-25 ºC. tert-Butyl tosylcarbamate (50.00 g, 184.3 mmol) was added at 15-25 ºC. K2CO3 (30.57 g, 221.2mmol) and KI (3.06 g, 202.7 mmol) were added to the solution at 15-25 ºC, and warmed under nitrogen at 30 ºC for 20 hrs. The solution was cooled to 20 ºC and the mixture filtered. The filtered residue was washed with MeCN (100 mL) to give methyl (E)-4-((N-(tert-butoxycarbonyl)-4-methylphenyl)sulfonamido)but-2-enoate. TFA (101.03 g, 886.06 mmol) was added to the methyl (E)-4-((N-(tert-butoxycarbonyl)-4-methylphenyl)sulfonamido)but-2-enoate in MeCN solution (483.72 g, 143 mmol) and heated to 55-60 ºC for 16 hrs. The reaction solution was concentrated in vacuo to ~50 mL and solvent exchanged with toluene (2 x 250 mL). Toluene (500 mL) was added followed by EtOAc (50 mL) at 15-25 °C, and heated to 60 ºC for 1 hr., then cooled to 0 ºC for 12 hrs. The solution was filtered, and the wet cake was rinsed with n-heptane (50 mL). The cake was dried in vacuum at 50 ºC to give the title compound (37.85 g, 74.4%) as a white solid.1H NMR (CDCl3) δ 7.68 (d, J = 8.0Hz, 2H) 7.25 (d, J = 8.0Hz, 2H) 6.71 (dt, J = 15.6, 5.2Hz, 1H) 5.88 (dt, J = 15.6, 1.6Hz, 1H) 4.55 (t, J = 6.4Hz, 1H) 3.71 – 3.67 (m, 2H) 3.65 (s, 3H) 2.37 (s, 3H); HRMS (ESI+) Calculated for [C12H15NO4S+H] +: 270.0795, Found: 270.0788 (M+H).
Preparation 2
[0083] (1R,5S,6r)-3-Tosyl-3-azabicyclo[3.1.0]hexane-6-carboxylic acid
0084] Methyl (E)-4-((4- 2-enoate (51.90 g) was dissolved in 2-MeTHF (600mL) at 0 ºC . Added (2-bromoethyl)diphenylsulfonium triflate (36.50 g), KF (6.47 g), KOH (18.75 g) to the solution at 0 ºC. Warmed the solution to 15 ºC for 22 hrs. then 30 ºC for 3 hrs. Added water (100 mL) and MeOH (100 mL) into the solution. Added LiOH.H2O (4.77 g) and stirred at 30 ºC for 16 hrs. Cooled to 15-25oC and added n-heptane (100 mL). Stirred at 15-25oC for 10 min. Separated and collected the aqueous phase and washed the aqueous phase with n-heptane/2-MeTHF (50 mL/200 mL × 2). Concentrated the aqueous phase in vacuo to ~50 mL and added 3M aq. HCl
dropwise to adjust pH to 1~2. Stirred the mixture at 20-30 ºC for 2 hrs. Filtered the solution and rinsed through with EtOH/H2O (15 mL1:4). Dried the wet cake at 45 ºC for 8-10 hrs. to give the title compound as white solid (20.37 g, 65%) 1H NMR (CDCl3) δ 7.67 (d, J = 8.2 Hz, 2 H) 7.34 (d, J = 8.2 Hz, 2 H) 3.63 (d, J = 9.4 Hz, 2 H) 3.12 (d, J = 9.4 Hz, 2 H) 2.46 – 2.40 (m, 4 H) 2.07 – 2.01 (m, 2 H); HRMS (ESI+) Calcd. for [C13H15NO4S+H] +: 282.0795, Found: 282.0795 (M+H).
Preparation 3
[0085] 2-Methyl-1-((3-methylpyridin-2-yl)oxy)propan-2-amine
0086] 2-Amino-2-methylpropan- mmol) was dissolved in toluene (250 mL) at 15-25 ºC. Added potassium tert-butoxide (60.59 g, 534.6 mmol) to the solution and warmed to 30-40 ºC. Added 2-fluoro-3-methylpyridine (50.00 g, 450.0 mmol) to the solution and warmed to 80 ºC. Stirred the mixture for 18 hrs. at 80 ºC. Cooled the mixture to 15-25 ºC, added water (100 mL) and stirred for 30 min. Separated the aqueous layer and washed the organics with 10% aq. NaCl (300 mL x 3). Added toluene (250 mL) to the organics and concentrated in vacuo to give the title compound as a liquid (107.50 g, 98%). 1H NMR (CDCl3) δ 7.92 – 7.82 (m, 1H) 7.32 – 7.22 (m, 1H) 6.74 – 6.66 (m, 1H) 3.97 (s, 3H) 2.14 (s, 3H) 1.15 (s, 6H).
Preparation 4
[0087] (1R,5S,6r)-N-(2-Methyl-1-((3-methylpyridin-2-yl)oxy)propan-2-yl)-3-tosyl-3-azabicyclo[3.1.0]hexane-6-carboxamide
[0088] Dissolved
6-carboxylic acid (32.33 g, 88.2% purity) in toluene (320 mL) at 15~25 ºC. Added DMF (741.0 mg) and (COCl)2 (19.20 g) to the solution and heated to 45-55 ºC for 3~4 hrs. Concentrated the mixture in vacuo and exchanged with THF (100 mL × 2). Added THF (320 mL) and cooled to 0-10 ºC. Added 2-methyl-1-((3-methylpyridin-2-yl)oxy)propan-2-amine (23.60 g), TEA (30.80 g), DMAP (620.0 mg) at 0-10 ºC then warmed to 15-25 ºC for 2~4 hrs.
Concentrated the mixture in vacuo and solvent exchanged with EtOH (140 mL × 2). Concentrated in vacuo to 140 mL and heated to 50 ºC until the solid was dissolved. Added water (210 mL) dropwise into the solution at 40 ºC. Cooled the solution to 10 ºC for 14 hrs. Filtered and rinsed with EtOH/H2O (75 mL, 1:1.5). Dried the wet cake at 45 ºC for 20 hrs. to give the title compound as a solid (41.87 g, 87.4%).1H NMR (CDCl3) δ 7.94 – 7.87 (m, 1 H) 7.60 (d, J=8.0 Hz, 2 H) 7.37 (d, J=6.6 Hz, 1 H) 7.26 (d, J=8.0 Hz, 2 H) 6.78 (dd, J=6.6, 5.0 Hz, 1 H) 6.48 (s, 1 H) 4.25 (s, 2 H) 3.52 (d, J=9.4 Hz, 2 H) 2.95 (d, J=9.4 Hz, 2 H) 2.39 – 2.33 (m, 3 H) 2.17 (s, 3 H) 1.84 (s, 2 H) 1.39 (s, 6 H); HRMS (ESI+) Calcd. for [C23H29N3O4S+H] +: 444.1952, Found: 444.2089 (M+H).
Preparation 5
[0089] (1R,5S,6r)-N-(2-Methyl-1-((3-methylpyridin-2-yl)oxy)propan-2-yl)-3-azabicyclo[3.1.0]hexane-6-carboxamide
[0090] Dissolved 2-yl)oxy)propan-2-yl)-3-tosyl-3-azabicyclo[3.1.0]hexane-6-carboxamide (5.00 g) in MTBE (50 mL) under nitrogen. Cooled to -70-60 ºC and added dropwise 1M Ph2PK in THF (56 mL, 56 mmol) into the solution. Stirred the mixture for 6-8 hrs. at -70-60 ºC. Added 2M aq. HCl (50 mL) to the solution allowing the temperature to rise to 15-25 ºC. Separated and collected the aqueous phase and washed with 2-MeTHF (50 mL × 3). Added 2-MeTHF (50 mL) and adjusted the pH to 8~9 with K2CO3 powder. Separated and extracted the aqueous phase with 2-MeTHF (50 mL). Combined the organics and concentrated in vacuo to give the title compound as a yellow-brown solid (3.05 g, 89.4%) 1H NMR (CDCl3) δ 8.01 – 7.92 (m, 1 H) 7.45 – 7.36 (m, 1 H) 6.81 (dd, J=7.0, 5.0 Hz, 1 H) 6.39 (s, 1 H) 4.31 (s, 2 H) 3.09 – 2.89 (m, 4 H) 2.21 (s, 3 H) 1.94 – 1.86 (m, 2 H) 1.69 (s, 1 H) 1.47 (s, 6 H) 1.12 (t, J=2.8 Hz, 1 H); HRMS (ESI+) Calcd. for [C16H23N3O2+H] +: 290.1863, Found:
290.1917 (M+H).
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References
References
- Stevens R, Corradini L, Doods H (April 2019). “Preclinical Evaluation of Human Somatostatin Receptor 4 (hSSTR4) Agonist CNTX-0290 for Mixed Pain Conditions”. The Journal of Pain. 20 (4): S73. doi:10.1016/j.jpain.2019.02.092.
- Nguyen TH, Saito T, Chang W, Navarro A, Davies HM (March 2026). “Diastereoselective Cyclopropanation with Secondary Diazoacetamides to Access endo-Azabicyclo[3.1.0]hexane-6-carboxamides”. Organic Letters. 28 (9): 3063–3067. doi:10.1021/acs.orglett.6c00392. PMC 12973298. PMID 41729728.
 | |
| Clinical data | |
|---|---|
| Other names | LY3556050, CNTX-0290 |
| Identifiers | |
| IUPAC name | |
| CAS Number | 1638588-92-7 |
| PubChem CID | 86294067 |
| ChemSpider | 77005706 |
| UNII | D3M32WP3MH |
| ChEMBL | ChEMBL5874446 |
| Chemical and physical data | |
| Formula | C16H23N3O2 |
| Molar mass | 289.379 g·mol−1 |
| 3D model (JSmol) | Interactive image |
| SMILES | |
| InChI | |
PAT
- Novel methods for the preparation of 3-azabicylco[3.1,0]hexane-6-carboxamide derivativesPublication Number: WO-2025096300-A1Priority Date: 2023-10-30
- Methods for the preparation and dose regimens for use of sstr4 agonists and salts thereofPublication Number: WO-2024191686-A1Priority Date: 2023-03-10
- Methods for the preparation and dose regimens for use of sstr4 agonists and salts thereofPublication Number: US-2024307349-A1Priority Date: 2023-03-10
- Methods for preparation and dose regimens for use of sstr4 agonists and salts thereofPublication Number: JP-2024170613-APriority Date: 2023-03-10
- Methods for the preparation of SSTR4 agonists and their salts and dosage regimens for usePublication Number: JP-7569953-B2Priority Date: 2023-03-10Grant Date: 2024-10-18
- Sstr4 agonist saltsPublication Number: US-2024067628-A1Priority Date: 2021-09-14
- SSTR4 agonist saltsPublication Number: US-11834435-B2Priority Date: 2021-09-14Grant Date: 2023-12-05
- New somatostatin receptor subtype 4 (sstr4) agonistsPublication Number: EP-2997021-B1Priority Date: 2013-05-17Grant Date: 2017-12-20
- Somatostatin receptor subtype 4 (SSTR4) agonistsPublication Number: US-9371282-B2Priority Date: 2013-05-17Grant Date: 2016-06-21
- Somatostatin receptor subtype 4 (SSTR4) agonistsPublication Number: US-10166214-B2Priority Date: 2013-05-17Grant Date: 2019-01-01
- New somatostatin receptor subtype 4 (sstr4) agonistsPublication Number: US-2019269650-A1Priority Date: 2013-05-17
- New somatostatin receptor subtype 4 (sstr4) agonistsPublication Number: WO-2014184275-A1Priority Date: 2013-05-17
- Somatostatin receptor subtype 4 (SSTR4) agonistsPublication Number: US-10675268-B2Priority Date: 2013-05-17Grant Date: 2020-06-09
- New Somatostatin receptor subtype 4 (SSTR4) agonistsPublication Number: US-2014343065-A1Priority Date: 2013-05-17
- Somatostatin receptor subtype 4 (SSTR4) agonistsPublication Number: US-9789082-B2Priority Date: 2013-05-17Grant Date: 2017-10-17
- New somatostatin receptor subtype 4 (sstr4) agonistsPublication Number: US-2017014381-A1Priority Date: 2013-05-17
- Somatostatin receptor subtype 4 (sstr4) agonistsPublication Number: US-2018092880-A1Priority Date: 2013-05-17
////////mazisotine, ANAX LABS, somatostatin receptor receptor agonist, LY3556050, CNTX-0290, LY 3556050, CNTX 0290, D3M32WP3MH, PAIN, NEUROPATHIC PAIN
DR ANTHONY MELVIN CRASTO
ORGANIC SPECTROSCOPY
New Drug Approvals 
