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Zanvipixant
Zanvipixant
CAS 2166558-11-6
MF C17H12F5N7O MW 425.3 g/mol
[(6S)-1-(5-fluoropyrimidin-2-yl)-6-methyl-6,7-dihydro-4H-triazolo[4,5-c]pyridin-5-yl]-[3-fluoro-2-(trifluoromethyl)-4-pyridinyl]methanone
[(6S)-1-(5-fluoropyrimidin-2-yl)-6-methyl-1,4,6,7-tetrahydro-5H-[1,2,3]triazolo[4,5-c]pyridin-5-yl][3-fluoro-2-
(trifluoromethyl)pyridin-4-yl]methanone
purinoreceptor (P2X) antagonist, JNJ-55308942, JNJ 55308942, B7YN3CQ7S7,
JNJ-55308942 is under investigation in clinical trial NCT05328297 (A Study of JNJ-55308942 in the Treatment of Bipolar Depression).
JNJ-55308942 is an investigational drug that works as a P2X7 antagonist with a downstream effect of reducing interleukin-1β release.[1][2][3] It is developed by Janssen Pharmaceuticals for bipolar depression.[4]
Zanvipixant (JNJ-55308942) is an investigational small-molecule, brain-penetrant, and potent antagonist of the P2X7 receptor developed by Janssen (J&J). It is primarily studied for its potential to treat neuroinflammation-related conditions, including mood disorders and depression, by inhibiting P2X7-mediated IL-1β release.
Key Details for Zanvipixant:
- Target: P2X7 Receptor (P2X7R).
- Mechanism: Brain-penetrant antagonist reducing neuroinflammation, specifically inhibiting microglial IL-1β release.
- Chemical Properties: Structure typically includes a triazolopyridine moiety.
- Development Status: Evaluated as a potential CNS treatment for conditions related to neuroinflammation, with research highlighting its pharmacological profile, including good CNS partitioning.
- Alternative Name: JNJ-55308942.
Research indicates that the P2X7 receptor is activated by high levels of extracellular ATP during stress, leading to inflammation and behavioral deficits associated with depression. Zanvipixant has been studied in this context as a potential therapeutic intervention.
- A Study of JNJ-55308942 in the Treatment of Bipolar DepressionCTID: NCT05328297Phase: Phase 2Status: CompletedDate: 2025-07-11
- A Study in Healthy Participants to Evaluate the Effects of Multiple Doses of JNJ-55308942 on Cytochrome P450 Substrate Activity and on the Pharmacokinetics of Levonorgestrel/Ethinyl EstradiolCTID: NCT03547024Phase: Phase 1Status: CompletedDate: 2025-04-27
- A Positron Emission Tomography (PET) Study to Investigate P2X7 Receptor Occupancy by JNJ-55308942 Using [18F]-JNJ-64413739CTID: NCT03437590Phase: Phase 1Status: CompletedDate: 2025-04-27
- A Study to Investigate the Safety, Tolerability, and Pharmacokinetics of JNJ-55308942 in Healthy Male and Female ParticipantsCTID: NCT03151486Phase: Phase 1Status: CompletedDate: 2025-04-27
- A Randomized, Stratified, Double-blind, Placebo-Controlled Study to Investigate the Efficacy, Safety and Tolerability of JNJ-55308942 in Bipolar Depression
- EudraCT: 2021-004790-31
- Phase: Phase 2
- Status: Ongoing, Completed
- Date: 2022-05-31
SYN
Publication Name: Journal of Medicinal Chemistry
Publication Date: 2017-12-20
PMID: 29211470
DOI: 10.1021/acs.jmedchem.7b01279
SYN
Example 228
(S*)-(3-fluoro-2-(trifluoromethyl)pyridin-4-yl)(1-(5-fluoropyrimidin-2-yl)-6-methyl-6,7-dihydro-1H-[1,2,3]triazolo[4,5-c]pyridin-5(4H)-yl)methanone
MS (ESI) mass calcd C 17H 12F 5N 7O, 425.1 m/z. found, 426.1 [M+H] +.
PAT
Example 228 (S)-(3 -fluoro-2-(trifluoromethyl)pyridin-4-yl)( 1 -(5 -fluoropyrimidin-2-yl)-6-methyl-6J-dihvdro-lH-ri,2,31triazolor4,5-c1pyridin-5(4H)-yl)methanone
he title compound was prepared as described in Example 65, substituting (S)-l-(5-fluoropyrimidin-2-yl)-6-methyl-4,5,6,7-tetrahydro-lH-[l,2,3]triazolo[4,5-c]pyridine-hydrochloride salt (prepared as Step 2 intermediate of method II synthesis) in Example 220 for l-pyrimidin-2-yl-4,5,6,7-tetrahydro-lH-[l,2,3]triazolo[4,5-c]pyridine, 3-fluoro-2-(trifluoromethyl)isonicotinic acid for 2-chloro-3-(trifluoromethyl)benzoic acid and Hunig’s base (3.0 equiv) for Et3N. The powder x-ray diffraction pattern for this compound is shown in Figure 2. Alternatively, the title compound was synthesized using the following procedure:
Step 1 : (S)-l-(3-fluoro-2-(trifluoromethyl)isonicotinoyl)-2-methylpiperidin-4-one
(S)-l-(3-fluoro-2-(trifluoromethyl)isonicotinoyl)-2-methylpiperidin-4-one.: (S)-2-methylpiperidin-4-one, TFA salt (108 g, 478 mmol, 1.0 equiv.) was suspended in DCM (1.4 L). Et3 (265 mL, 1.9 mol, 4.0 equiv.) and 3-fluoro-2-(trifluoromethyl)isonicotinoyl
chloride (1 19 g, 526 mmol, 1.1 equiv.) were added sequentially. The reaction solution was stirred at room temperature for 1 h. The precipitated solid was filtered and washed with EtOAc. The filtrate solution was concentrated and the residue was re-dissolved in EtOAc (500 mL). The organic layer was washed with saturated aHC03 aqueous solution, water and brine, dried over Na2S04, and concentrated. The crude product was triturated from EtOAc/hexanes to afford (S)-l-(3-fluoro-2-(trifluoromethyl)isonicotinoyl)-2-methylpiperidin-4-one (103 g, 368 mmol, 77%), which was used without further purification. MS = 305.1 (positive mode)
Step 2: (S)-(3-fluoro-2-(trifluoromethyl)pyridin-4-yl)(l-(5-fluoropyrimidin-2-yl)-6-methyl-6,7-dihvdro-lH-ri ,2,31triazolor4,5-c1pyridin-5(4H)-yl)methanone and (S)-(3-fluoro-2-(trifluoromethyl)pyridin-4-yl)(l-(5-fluoropyrimidin-2-yl)-4-methyl-6J-dihydro-lH
[ 1.2.3 Itriazolo [4.5 -c]pyridin-5 (4H)-yl)methanone
In a 5 L, three-neck, round-bottom flask equipped with a mechanic stirring, Dean-Stark trap, reflux condenser and an internal thermometer, to the solution of (S)-l-(3-fluoro-2-(trifluoromethyl)isonicotinoyl)-2-methylpiperidin-4-one, prepared in Step 1 above (100 g, 328 mmol, 1.0 equiv.) in toluene (1.5 L), -toluenesulphonic acid (0.62 g, 3.29 mmol, 0.01 equiv.), pyrrolidine (33 mL, 394 mmol, 1.2 equiv.) and 2-azido-5-fluoropyrimidine (59.4 g, 427 mmol, 1.3 equiv.) were added sequentially. The reaction mixture was heated to reflux temperature for 4 hours and then cooled to room temperature. aHC03 (55.2 g, 657 mmol, 2.0 equiv.) and mCPBA (162 g, 657 mmol, 2.0 equiv.) solution in EtOAC (-250 mL) were added sequentially. After stirring at room temperature for 2 hours, water and EtOAc were added. The organic layer was washed sequentially with 1M a2S03, saturated aHC03 aqueous solution, and brine, dried over Na2S04, and concentrated. The crude product was purified via column chromatography to afford a mixture of (S)-(3-fluoro-2-
(trifluoromethyl)pyridin-4-yl)(l-(5-flu^
[l,2,3]triazolo[4,5-c]pyridin-5(4H)-yl)methanone and (S)-(3-fluoro-2- (trifluoromethyl)pyridin-4-yl)(l-(5-fl^^
[l,2,3]triazolo[4,5-c]pyridin-5(4H)-yl)methanone in a 10: 1 ratio (97 grams).
Step 3 : (S)-(3-fluoro-2-(trifluoromethyl)pyridin-4-yl)(l -(5-fluoropyrimidin-2-yl)-6-methyl-6.7-dihvdro-lH-ri.2.31triazolor4.5-c1pyridin-5(4H)-yl)methanone
HPLC purification of the mixture from Step 2 was performed via achiral SFC (Stationary phase: Chiralcel OD-H 5μιη 250x30mm), (Mobile phase: 75% C02, 25% MeOH) to afford pure (S)-(3-fluoro-2-(trifluoromethyl)pyridin-4-yl)(l-(5-fluoropyrimidin-2-yl)-6-methyl-6,7-dihydro-lH-[l,2,3]triazolo[4,5-c]pyridin-5(4H)-yl)methanone (73 gram, 172 mmol, 52%). MS (ESI) mass calcd Ci7H12F5 70, 425.1 m/z found, 426.1 [M+H]+. XH NMR (500 MHz, CDC13) δ 8.84 – 8.69 (m, 2H), 8.68 – 8.57 (m, 1H), 7.71 – 7.49 (m, 1H), 5.90 -5.68 (d, J = 16.4 Hz, 0.5H), 5.66 – 5.54 (m, 0.5H), 4.76 – 4.58 (d, J = 15.8 Hz, 0.5H), 4.58 – 4.48 (m, 0.5H), 4.45 – 4.33 (m, 0.5H), 4.20 – 4.09 (m, 0.5H), 3.56 – 3.12 (m, 2H), 1.48 -1.18 (m, 3H).
2-chloro-3-(trifluoromethyl)benzoic acid and Hunig’s base (3.0 equiv) for Et3N. MS (ESI) mass calcd Ci7H12F5 70, 425.1 m/z found, 426.1 [M+H]+.
PAT
- P2X7 modulatorsPublication Number: US-9464084-B2Priority Date: 2013-03-14Grant Date: 2016-10-11
- P2X7 MODULATORSPublication Number: PT-2970267-TPriority Date: 2013-03-14
- P2X7 modulatorsPublication Number: US-11225478-B2Priority Date: 2013-03-14Grant Date: 2022-01-18
- P2X7 modulatorPublication Number: JP-6293861-B2Priority Date: 2013-03-14Grant Date: 2018-03-14
- P2X7 modulatorsPublication Number: AU-2019203186-A1Priority Date: 2013-03-14
- P2X7 modulatorsPublication Number: TW-201446762-APriority Date: 2013-03-14
- P2X7 regulatorsPublication Number: CN-110003200-APriority Date: 2013-03-14
- P2X7 modulatorsPublication Number: US-9066946-B2Priority Date: 2013-03-14Grant Date: 2015-06-30
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References
“CTG Labs – NCBI”. clinicaltrials.gov. Retrieved 27 November 2023.
Bhattacharya, Anindya; Lord, Brian; Grigoleit, Jan-Sebastian; He, Yingbo; Fraser, Ian; Campbell, Shannon N.; Taylor, Natalie; Aluisio, Leah; O’Connor, Jason C.; Papp, Mariusz; Chrovian, Christa; Carruthers, Nicholas; Lovenberg, Timothy W.; Letavic, Michael A. (December 2018). “Neuropsychopharmacology of JNJ-55308942: evaluation of a clinical candidate targeting P2X7 ion channels in animal models of neuroinflammation and anhedonia”. Neuropsychopharmacology. 43 (13): 2586–2596. doi:10.1038/s41386-018-0141-6. ISSN 0893-133X. PMC 6224414. PMID 30026598.
Bhattacharya, Anindya; Ceusters, Marc (January 2020). “Targeting neuroinflammation with brain penetrant P2X7 antagonists as novel therapeutics for neuropsychiatric disorders”. Neuropsychopharmacology. 45 (1): 234–235. doi:10.1038/s41386-019-0502-9. ISSN 0893-133X. PMC 6879571. PMID 31477815.
Kolb, Hartmuth C.; Barret, Olivier; Bhattacharya, Anindya; Chen, Gang; Constantinescu, Cristian; Huang, Chaofeng; Letavic, Michael; Tamagnan, Gilles; Xia, Chunfang A.; Zhang, Wei; Szardenings, Anna Katrin (August 2019). “Preclinical Evaluation and Nonhuman Primate Receptor Occupancy Study of 18 F-JNJ-64413739, a PET Radioligand for P2X7 Receptors”. Journal of Nuclear Medicine. 60 (8): 1154–1159. doi:10.2967/jnumed.118.212696. ISSN 0161-5505. PMID 30733317. S2CID 73454130.
| Clinical data | |
|---|---|
| Trade names | Zanvipixant |
| Legal status | |
| Legal status | Investigational New Drug |
| Identifiers | |
| IUPAC name | |
| CAS Number | 2166558-11-6 |
| PubChem CID | 90408860 |
| DrugBank | DB19110 |
| ChemSpider | 76771276 |
| UNII | B7YN3CQ7S7 |
| ChEMBL | ChEMBL3914857 |
| Chemical and physical data | |
| Formula | C17H12F5N7O |
| Molar mass | 425.323 g·mol−1 |
| 3D model (JSmol) | Interactive image |
| SMILES | |
| InChI | |
////////zanvipixant, ANAX LAB, purinoreceptor (P2X) antagonist, JNJ-55308942, JNJ 55308942, B7YN3CQ7S7,
Vormatrigine
Vormatrigine
CAS 2392951-18-5
MF C16H12F6N4O2 MW406.28 g/mol
3-(ethoxydifluoromethyl)-6-(5-fluoro-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)-[1,2,4]triazolo[4,3-a]pyridine
3-[ethoxydi(fluoro)methyl]-6-[5-fluoro-6-(2,2,2-trifluoroethoxy)pyridin-3-yl][1,2,4]triazolo[4,3-a]pyridine
sodium channel blocker, PRAX-628, PRAX 628, QU3C48T4NV,
Vormatrigine is a small molecule drug. The usage of the INN stem ‘-trigine’ in the name indicates that Vormatrigine is a sodium channel blocker, signal transduction modulator. Vormatrigine has a monoisotopic molecular weight of 406.09 Da.
Vormatrigine (formerly PRAX-628) is an oral, small-molecule, voltage-gated sodium channel inhibitor being developed by Praxis Precision Medicines for focal onset and generalized epilepsy. Phase II RADIANT trial data indicated that 22% of participants achieved complete seizure freedom, with a 56.3% median reduction in seizure frequency. IGMPI +2
Key Aspects of Vormatrigine:
- Mechanism: Targets the hyperexcitable state of NaV channels, acting as a functional state modulator.
- Efficacy: In the Phase II RADIANT trial (NCT06908356) for focal epilepsy, the drug showed significant seizure reduction (56.3% median reduction), with 60% of participants achieving a $\ge$50% reduction in seizures.
- Dosing: Developed for once-daily, oral administration without the need for complex titration.
- Safety Profile: Vormatrigine was generally well-tolerated in clinical studies, with mostly mild, transient adverse events reported, as noted in the Phase 1 PRAX-628-102 study.
- Future Development: Praxis is moving forward with Phase III trials (POWER2) following the successful Phase II results, with plans to potentially redefine treatment for patients with treatment-resistant focal epilepsy.
- Drug-Drug Interactions: Preliminary data suggests a favorable profile with minimal interaction risks, supporting its potential use in polytherapy.
Neurology Live +4
The drug is expected to be a major competitor in the epilepsy market if approved, with potential for high sales due to its efficacy profile compared to existing treatments. IGMPI
SYN
WO2019232209A1
- Assignee: Praxis Precision Medicines
- Title: Pyridin-3-yl substituted triazolopyrazines / triazolopyridines
- Year: 2019
- Covers:
- Vormatrigine structure (explicitly or as a close analog)
- General synthetic routes
- Multiple heterocycle construction strategies
This is the core patent used by all CRO/CDMO reverse synthesis work.Example ~178
Patent Landscape
The primary patent coverage for Vormatrigine and its related analogs is held by Praxis Precision Medicines, Inc. The chemical structure is a 1,2,4-triazolo[4,3-a]pyridine derivative.
- Primary Compound Patent:WO 2020/033839 (and its US equivalent US 11,447,489).
- Title: Preparation of pyridin-3-yl substituted triazolopyrazines, triazolopyridazines, and triazolopyridines as ion channel modulators.
- Scope: This patent covers the specific structure of Vormatrigine (Example 167 in some filings) and its use as a voltage-gated sodium channel (VGSC) inhibitor.
- Other Relevant Filings: * WO 2022/173918: Focuses on specific crystalline forms (polymorphs) and manufacturing improvements.
- CN 116444437 / CN 111087324: While these specific numbers often relate to broader triazolopyridine research (like Darolutamide, which you’ve researched previously), Praxis holds several Chinese counterparts for the PRAX-628 series.
SYN
SYN
Example 3: 3-[ethoxy(difluoro)methyl]-6-[5-fluoro-6-(2,2,2-trifluoroethoxy)-3-pyridyl]-[1,2,4]triazolo[4,3-a]pyridine
| Synthesis of A5: A mixture of 6-bromo-3-[chloro(difluoro)methyl]-[1,2,4]triazolo[4,3-a]pyridine (300 mg, 1.06 mmol) and EtONa (361.37 mg, 5.31 mmol) in Ethanol (10 mL) was stirred at 80° C. for 24 hours. After cooling to room temperature, the reaction was quenched with sat.NH 4Cl (10 mL), and the mixture was extracted with EtOAc (20 mL×2). The combined organic phase was washed with brine (10 mL), dried over Na 2SO 4, filtered and concentrated to give the crude product. The crude product was purified by flash chromatography on silica gel (EtOAc in PE=10% to 40%) to give the product (70 mg, 0.17 mmol) as a solid. LCMS R t=1.97 min in 4 min chromatography, MS ESI calcd. C 9H 9BrF 2N 3O [M+H+2] + 294.0, found 293.8. |
SYN
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REF
PAT
- Ion channel modulatorsPublication Number: TW-202012403-APriority Date: 2018-05-30
- 3-(ethoxydifluoromethyl)-6-(5-fluoro-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)-[1,2,4]triazolo[4,3-a]pyridine as an ion channel modulatorPublication Number: US-11731978-B2Priority Date: 2018-05-30Grant Date: 2023-08-22
- Ion channel modulatorsPublication Number: EP-3801535-A1Priority Date: 2018-05-30
- Ion channel modulatorsPublication Number: EP-4487916-A2Priority Date: 2018-05-30
- Ion channel modulatorsPublication Number: US-2022024930-A1Priority Date: 2018-05-30
- 3-(ethoxydifluoromethyl)-6-(5-fluoro-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)-[1,2,4]triazolo[4,3-a]pyrazine as an ion channel modulatorPublication Number: US-11014931-B2Priority Date: 2018-05-30Grant Date: 2021-05-25
- Ion channel modulatorPublication Number: KR-20210024500-APriority Date: 2018-05-30
- Ion channel modulatorsPublication Number: US-2021163488-A1Priority Date: 2018-05-30
- Ion channel modulatorsPublication Number: US-2022220118-A1Priority Date: 2018-05-30
- 3-(ethoxydifluoromethyl)-6-(5-fluoro-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)-[1,2,4]triazolo[4,3-a]pyridine as an ion channel modulatorPublication Number: US-11731976-B2Priority Date: 2018-05-30Grant Date: 2023-08-22
- Treatment of neurological disordersPublication Number: WO-2023211859-A1Priority Date: 2022-04-26
- Methods for the treatment of neurological disordersPublication Number: WO-2023211856-A1Priority Date: 2022-04-26
- Ion channel modulatorsPublication Number: US-11866439-B2Priority Date: 2018-05-30Grant Date: 2024-01-09
- Ion channel modulatorsPublication Number: US-2024132501-A1Priority Date: 2018-05-30
- Ion channel modulatorsPublication Number: US-2021087197-A1Priority Date: 2018-05-30
////////////vormatrigine, ANAX LAB, sodium channel blocker, PRAX-628, PRAX 628, QU3C48T4NV,
Veonetinib
Veonetinib
👉CAS 1210828-09-3
MF C27H28FN3O4 MW 477.5 g/mol
5-[2-[4-[(4-fluoro-2-methyl-1H-indol-5-yl)oxy]-6-methoxyquinolin-7-yl]oxyethyl]-5-azaspiro[2.4]heptan-7-ol
5-AZASPIRO(2.4)HEPTAN-7-OL, 5-(2-((4-((4-FLUORO-2-METHYL-1H-INDOL-5-YL)OXY)-6-METHOXY-7-QUINOLINYL)OXY)ETHYL)-
5-(2-(4-(4-fluoro-2-methyl-1H-indol-5-yloxy)-6-methoxyquinolin-7-yloxy)ethyl)-5-azaspiro[2.4]-heptan-7-ol
(7RS)-5-[2-({4-[(4-fluoro-2-methyl-1H-indol-5-yl)oxy]-6-methoxyquinolin7-yl}oxy)ethyl]-5-azaspiro[2.4]heptan-7-ol
tyrosine kinase inhibitor, antineoplastic, U7PA8S6XGJ
👉SYN
Example 3
5-(2-(4-(4-fluoro-2-methyl-lH-indol-5-yloxy)-6-methoxyquinolin-7-yloxy)ethyl)-5-azaspiro[2.4]-heptan-7-ol
The above product from Example 2 (75 mg) was dissolved into MeOH (8 ml) and stirred at RT.
NaBH4 (75 mg) was added to the reaction and stirred at RT for 30 min. The reaction was evaporated and purified by column chromatography to give title compound (60 mg). Mass: (M + 1), 478
Patent Scope
- Covers:
- Quinoline–indole kinase inhibitors
- VEGFR / angiogenesis targets
- Broad Markush structures
Fragment A: Indole Phenol
4-fluoro-2-methyl-1H-indol-5-ol
Typical Preparation
- Fischer indole synthesis or substituted aniline cyclization
- Fluorination / directed substitution
- Hydroxyl introduction at C-5
Fragment B: Quinoline Electrophile
4-chloro-6-methoxy-7-(leaving group) quinoline
Typical Route
- Start from 6-methoxyaniline
- Skraup / Doebner–Miller → quinoline core
- Chlorination at C-4
- Functionalization at C-7 (OH or halide)
Fragment C: Chiral Spiro Amine
(R)-5-azaspiro[2.4]heptan-7-ol
- Usually from:
- Chiral pool OR
- Resolution of racemate
- Important: defines final stereochemistry
4. STEP-BY-STEP SYNTHESIS (PATENT-ALIGNED)
Step 1: Indole–Quinoline Ether Formation
Reaction: SNAr / Ullmann-type coupling
Indole phenol + 4-chloroquinoline → aryl ether
Conditions
- Base: K2CO3 / Cs2CO3
- Solvent: DMF / DMSO
- Temp: 80–120°C
Forms:
Indole–O–quinoline core
Step 2: Introduction of Linker (C-7 substitution)
If quinoline has OH:
Quinoline–OH + Br–CH2–CH2–X → O–CH2CH2–X
If halide:Direct alkylation
Conditions
- Base: NaH / K2CO3
- Solvent: DMF
- Temp: 50–90°C
Product:
Quinoline–O–CH2CH2–X
Step 3: Coupling with Spiro Amine
Quinoline–O–CH2CH2–X + spiro amine → final amine linkage
Reaction Type
- SN2 substitution
Conditions
- Base: DIPEA / Et3N
- Solvent: ACN / DMF
- Temp: 50–80°C
Step 4: Final Deprotection / Purification
- Remove protecting groups (if any)
- Chiral purity control
- Crystallization
Step 1: Preparation of Indole–Quinoline Ether
Starting materials:
- 4-fluoro-2-methyl-1H-indol-5-ol
→ 1.00 equiv (e.g., 5.0 g, ~30 mmol) - 4-chloro-6-methoxyquinoline
→ 1.10 equiv (~33 mmol)
Reagents:
- Potassium carbonate (K₂CO₃) → 2.0 equiv (~60 mmol)
- Solvent: DMF (50–60 mL)
Procedure:
- Charge indole phenol and K₂CO₃ in DMF under nitrogen.
- Add 4-chloroquinoline portionwise.
- Heat to 100–110°C.
- Stir for 8–12 h.
Workup:
- Cool to RT
- Pour into water (200 mL)
- Extract with EtOAc (3×)
- Wash with brine, dry (Na₂SO₄)
- Concentrate
Purification:
- Silica gel chromatography (EtOAc/hexane)
Yield: ~70–80%
Product: Indole–quinoline ether intermediate
Step 2: Installation of Ethylene Linker
Starting material: Step 1 product (~25 mmol)
Reagents:
- 1,2-dibromoethane → 1.5–2.0 equiv
- Base: K₂CO₃ → 2 equiv
- Solvent: DMF (40 mL)
Procedure:
- Dissolve intermediate in DMF
- Add K₂CO₃
- Add dibromoethane
- Heat to 80–90°C for 6–8 h
Workup:
- Pour into water
- Extract with EtOAc
- Dry and concentrate
Product: Quinoline–O–CH₂CH₂–Br
Yield: ~65–75%
Step 3: Coupling with Chiral Spiro Amine
Starting materials:
- Bromo intermediate → 1.0 equiv (~15–20 mmol)
- (R)-5-azaspiro[2.4]heptan-7-ol → 1.2 equiv
Reagents:
- DIPEA or Et₃N → 2 equiv
- Solvent: Acetonitrile or DMF (30–40 mL)
Procedure:
- Combine bromo intermediate and amine in solvent
- Add DIPEA
- Heat to 60–70°C
- Stir 12–16 h
Workup:
- Remove solvent
- Dissolve in EtOAc
- Wash with water + brine
- Dry and concentrate
Yield: ~70–85%
Step 4: Final Purification
Purification options:
- Silica chromatography OR
- Recrystallization (EtOAc/hexane or IPA)
Optional:
- Convert to pharmaceutically acceptable salt
Final Yield (overall): ~35–45%
PAT
EXAMPLE 1
4-(4-Fluoro-2-methyl-1H-indol-5-yloxy)-6-methoxy-7-[2-(5,8-Dioxa-10-azadispiro[2.0.4.3]-undecane)ethoxy]quinoline
Preparation of 4-(4-fluoro-2-methyl-1H-indol-5-yloxy)-6-methoxy-7-benzyloxyquinoline
Method A:
Method B:
Preparation of Title Compound
Method C:
Method D:
EXAMPLE 2
5-(2-(4-(4-Fluoro-2-methyl-1H-indol-5-yloxy)-6-methoxyquinolin-7-yloxy)ethyl)-5-azaspiro[2.4]-heptan-7-one
EXAMPLE 3
5-(2-(4-(4-fluoro-2-methyl-1H-indol-5-yloxy)-6-methoxyquinolin-7-yloxy)ethyl)-5-azaspiro[2.4]-heptan-7-ol
PAT
PAT
CN201710900497.6 CN201610649732.2 → leads to US10689361B2
PAT
- Compounds as kinase inhibitorsPublication Number: CA-2733250-CPriority Date: 2008-08-19Grant Date: 2016-06-21
- Compounds that act as kinase inhibitorsPublication Number: ES-2617678-T3Priority Date: 2008-08-19Grant Date: 2017-06-19
- Compounds as kinase inhibitorsPublication Number: WO-2010021918-A1Priority Date: 2008-08-19
- Compounds as kinase inhibitorsPublication Number: EP-2312950-A1Priority Date: 2008-08-19
- Compounds as kinase inhibitorsPublication Number: US-8211911-B2Priority Date: 2008-08-19Grant Date: 2012-07-03
- Compounds as kinase inhibitorsPublication Number: JP-2012500269-APriority Date: 2008-08-19
- Compounds as kinase inhibitorsPublication Number: KR-20110044749-APriority Date: 2008-08-19
- Compounds as kinase inhibitorsPublication Number: EP-2312950-B1Priority Date: 2008-08-19Grant Date: 2016-11-30
- Biological activities of 5-(2-(4-(4-fluoro-2-methyl-1h-indol-5-yloxy)-6-methoxyquinolin-7-yloxy)ethyl)-5-azaspiro[2.4]-heptan-7-ol crystalline, phosphoric acid salt and its enantiomersPublication Number: US-2023399313-A1Priority Date: 2022-06-10
- Btological activities of 5-(2-(4-(4-fluoro-2-methyl-1h-indol-5- yloxy)-6-methoxyquinolin-7-yloxy)ethyl)-5-azaspiro[2.4]-heptan- 7-ol crystalline, phosphoric acid salt and its enantiomersPublication Number: WO-2023239945-A1Priority Date: 2022-06-10
- Btological activities of 5-(2-(4-(4-fluoro-2-methyl-1h-indol-5- yloxy)-6-methoxyquinolin-7-yloxy)ethyl)-5-azaspiro[2.4]-heptan- 7-ol crystalline, phosphoric acid salt and its enantiomersPublication Number: EP-4536652-A1Priority Date: 2022-06-10
- Compounds as kinase inhibitorsPublication Number: CA-2733250-A1Priority Date: 2008-08-19
- Compounds As Kinase InhibitorsPublication Number: US-2010048599-A1Priority Date: 2008-08-19
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REF
//////////veonetinib, ANAX LAB, tyrosine kinase inhibitor, antineoplastic, U7PA8S6XGJ
Ulacamten
Ulacamten
CAS 2830607-59-3
MF C21H25F2N3O3 MW405.4 g/mol
5-[(3,4-difluorophenyl)methyl]-8-(4-methylcyclohexyl)-6,9-dioxo-2,5,8-triazaspiro[3.5]nonane-2-carbaldehyde
5-[(3,4-difluorophenyl)methyl]-8-[(1r,4r)-4-methylcyclohexyl]-6,9-dioxo-2,5,8-triazaspiro[3.5]nonane-2-carbaldehyde
cardiac myosin inhibitor, CK-586, CK-4021586, CK 586, CK 4021586, X325G97HZJ
Ulacamten (also known as CK-586 or CK-4021586) is an investigational drug developed by Cytokinetics that acts as a cardiac myosin inhibitor (CMI). It is currently being studied for the treatment of heart failure with preserved ejection fraction (HFpEF), a condition where the heart muscle is too stiff to fill properly
Key Characteristics and Development
- Mechanism of Action: Unlike earlier CMIs like mavacamten or aficamten, ulacamten is highly selective. It binds to the regulatory light chain (RLC) of myosin and only inhibits the “two-headed” form of cardiac myosin, potentially allowing for more precise control over heart muscle contraction.
- Clinical Status: As of March 2026, it is in Phase 2 clinical trials (specifically the AMBER-HFpEF study) to evaluate its safety, tolerability, and optimal dosage in patients with symptomatic HFpEF.
- Administration: It is designed as an orally active small molecule intended for once-daily dosing.
- Potential Benefits: Preclinical studies suggest it can reduce excessive myocardial contractility and improve left ventricular relaxation (diastolic function) without significantly compromising the heart’s overall pumping ability.
- AMBER-HFpEF: Assessment of CK-4021586 in a Multi-Center, Blinded Evaluation of Safety and Tolerability Results in HFpEFCTID: NCT06793371Phase: Phase 2Status: RecruitingDate: 2026-01-12
- A Single and Multiple Ascending Dose Study of CK-4021586 in Healthy Adult ParticipantsCTID: NCT05877053Phase: Phase 1Status: CompletedDate: 2025-05-01
SYN
Example 1
Synthesis of 5-(3,4-difluorobenzyl)-8-((1r,4r)-4-methylcyclohexyl)-6,9-dioxo-2,5,8-triazaspiro[3.5]nonane-2-carbaldehyde
(Compound 4)
Step 1: Synthesis of 1-(tert-butyl) 3-ethyl 3-((3,4-difluorobenzyl)amino)azetidine-1,3-dicarboxylate:
[0147] To a solution of 1-tert-butyl 3-ethyl 3-aminoazetidine-1,3-dicarboxylate (4.0 g, 16.4 mmol, 1.0 equiv) and 3,4-difluorobenzaldehyde (2.4 g, 19.6 mmol, 1.2 equiv) in DCE (40.0 mL) at 0 ˚C were added STAB (7.0 g, 32.8 mmol, 2.0 equiv) and AcOH (2.0 g, 32.8 mmol, 2.0 equiv). The resulting mixture was stirred at rt overnight, adjusted the pH to 8 with ammonium hydroxide, added water (50.0 mL) and extracted with DCM (50.0 mL) twice. The combined organic layers were washed with brine (50 mL) twice, dried over anhydrous Na 2 SO 4 , and concentrated under reduced pressure to afford 6.0 g of 1-tert-butyl 3-ethyl 3-(3,4-difluorobenzyl)amino)azetidine-1,3-dicarboxylate as a yellow oil. LRMS (ES) m/z 315 (M+H-56).
Step 2: Synthesis of 1-(tert-butyl) 3-ethyl 3-(2-bromo-N-(3,4-difluorobenzyl)acetamido)azetidine-1,3-dicarboxylate:
[0148] To a solution of 1-tert-butyl 3-ethyl 3-[[(3,4-difluorophenyl)methyl]amino]azetidine-1,3-dicarboxylate (6.0 g, 16.2 mmol, 1.0 equiv) in DCM (60.0 mL) at 0 ˚C were added a solution of K 2 CO 3 (3.4 g, 24.3 mmol, 1.50 equiv) in water (30 mL), and then bromoacetyl bromide (3.9 g, 19.4 mmol, 1.2 equiv) dropwise over a period of 10 min. The resulting mixture was stirred at rt overnight and extracted with DCM (50.0 mL) twice. The combined organic layers were washed with brine (100 mL) twice, dried over anhydrous Na 2 SO 4 , and concentrated under reduced pressure to afford 8.0 g of 1-(tert-butyl) 3-ethyl 3-(2-bromo-N-(3,4-difluorobenzyl)acetamido)azetidine-1,3-dicarboxylate as a yellow oil. LRMS (ES) m/z 435 (M+H-56).
Step 3: Synthesis of tert-butyl 5-(3,4-difluorobenzyl)-8-((1r,4r)-4-methylcyclohexyl)-6,9-dioxo-2,5,8-triazaspiro[3.5]nonane-2-carboxylate:
[0149] To a solution of 1-(tert-butyl) 3-ethyl 3-(2-bromo-N-(3,4-difluorobenzyl)acetamido)azetidine-1,3-dicarboxylate (8.0 g, 16.3 mmol, 1.0 equiv) in ACN (80 mL) were added TEA (4.9 g, 48.4 mmol, 3.0 equiv) and trans-(1r,4r)-4-methylcyclohexan-1-amine (2.8 g, 24.7 mmol, 1.5 equiv). The resulting mixture was stirred at rt for 1 h, gradually warmed to 80 ˚C, and stirred at 80 ˚C overnight. The mixture was cooled to rt, concentrated under reduced pressure, and triturated with a mixture of PE and EA (7/1; 80 mL) to afford 7 g (~80% purity) of tert-butyl 5-(3,4-difluorobenzyl)-8-((1r,4r)-4-methylcyclohexyl)-6,9-dioxo-2,5,8-triazaspiro[3.5]nonane-2-carboxylate as an off-white solid. LRMS (ES) m/z 422 (M+H-56).
Step 4: Synthesis of 5-(3,4-difluorobenzyl)-8-((1r,4r)-4-methylcyclohexyl)-2,5,8-triazaspiro[3.5]nonane-6,9-dione:
[0150] To a stirred solution of tert-butyl 5-(3,4-difluorobenzyl)-8-((1r,4r)-4-methylcyclohexyl)-6,9-dioxo-2,5,8-triazaspiro[3.5]nonane-2-carboxylate (7.0 g, 14.7 mmol, 1.0 equiv) in DCM (70.0 mL) was added TFA (18.0 mL). The resulting mixture was stirred at rt for 3h, diluted with water (100.0 mL), adjusted the pH to 13-14 with aqueous NaOH solution (2 N), and extracted with DCM (100 mL) twice. The combined organic layers were washed with brine (100.0 mL) twice, dried over anhydrous Na 2 SO 4 , and concentrated under reduced pressure to afford 4.5 g (~80% purity) of 5-(3,4-difluorobenzyl)-8-((1r,4r)-4-methylcyclohexyl)-2,5,8-triazaspiro[3.5]nonane-6,9-dione as a yellow semi-solid. LRMS (ES) m/z 378 (M+H).
Step 5: Synthesis of 5-(3,4-difluorobenzyl)-8-((1r,4r)-4-methylcyclohexyl)-6,9-dioxo-2,5,8-triazaspiro[3.5]nonane-2-carbaldehyde (Compound 4):
[0151] A solution of tert-butyl 5-(3,4-difluorobenzyl)-8-((1r,4r)-4-methylcyclohexyl)-6,9-dioxo-2,5,8-triazaspiro[3.5]nonane-2-carboxylate (1.5 g, 4.0 mmol, 1.0 equiv) in ethyl formate (15.0 mL) was stirred at 80
o C overnight. The mixture was cooled to rt, concentrated under reduced pressure, and purified by C18 column chromatography, eluted with a mixture of water (0.05% NH
4 HCO
3 )/CH
3 CN (3:2) to afford 1.3 g (81%) of 5-(3,4-difluorobenzyl)-8-((1r,4r)-4-methylcyclohexyl)-6,9-dioxo-2,5,8-triazaspiro[3.5]nonane-2-carbaldehyde as an amorphous white solid. An experimental X-ray powder diffraction (XRPD) pattern of this amorphous white solid is shown in FIG. 1 LRMS (ES) m/z 406 (M+H);
1 H NMR (300 MHz, DMSO-d6) δ 7.96 (s, 1H), 7.47 – 7.29 (m, 2H), 7.10 (ddd, J = 9.4, 4.4, 2.0 Hz, 1H), 4.82 (s, 2H), 4.50 (d, J = 9.6 Hz, 1H), 4.15-4.28 (m, J = 3H), 4.01 (s, 2H), 3.96 (d, J = 10.8 Hz, 1H), 1.80 – 1.69 (m, 2H), 1.65 – 1.48 (m, 4H), 1.35 (d, J = 10.9 Hz, 1H), 1.13 – 0.93 (m, 2H), 0.88 (d, J = 6.5 Hz, 3H).
PAT
5-(3,4-difluorobenzyl)-8-((1r,4r)-4-methylcyclohexyl)-6,9-dioxo-2,5,8-triazaspiro[3.5]nonane-2-carbaldehyde, also called compound 1, having the structure shown below,
Example 1
Synthesis of 5-(3,4-difluorobenzyl)-8-((1r,4r)-4-methylcyclohexyl)-6,9-dioxo-2,5,8-triazaspiro[3.5]nonane-2-carbaldehyde (Compound 1)
Step 6: Synthesis of 5-[(3,4-difluorophenyl)methyl]-6,9-dioxo-8-[(1r,4r)-4-methylcyclohexyl]-2,5,8-triazaspiro[3.5]nonane-2-carbaldehyde (Compound 1):
[0165] To a solution of 5-(3,4-difluorobenzyl)-8-((1r,4r)-4-methylcyclohexyl)-6,9-dioxo-2,5,8-triazaspiro[3.5]nonane-2-carbaldehyde (4.0 kg, 10.60 mol, 1 equiv) in MeCN (20 L) at r.t. were added 2,2,2-trifluoroethyl formate (1.63 kg, 12.72 mol, 1.2 equiv) and DIPEA (3.42 kg, 26.50 mol, 2.5 equiv) . The resulting mixture was stirred overnight at rt. The reaction was monitored by LCMS. The resulting mixture was concentrated under reduced pressure. The resulting mixture was diluted with EtOAc (10 L). The resulting mixture was quenched with NH 4Cl (6 L, sat.) and water (6 L), extracted with EtOAc (3×15 L). The combined organic layers were washed with NH 4Cl (aq.) (10 L) and brine (10 L), dried over anhydrous Na 2SO 4, concentrated under reduced pressure to give a crude brown oil, the crude oil was re-crystallized from cyclohexane and EtOAc (5:1, 4L, 80 °C to r.t.), filtered to afford 3 kg (1 st batch) 5-[(3,4-difluorophenyl)methyl]-6,9-dioxo-8-[(1r,4r)-4-methylcyclohexyl]-2,5,8-triazaspiro[3.5]nonane-2-carbaldehyde light yellow solid. The filtrate was concentrated under reduced pressure, re-crystallized with petroleum ether and EtOAc (10:1, 3 L, rt) to afford 800 g (2 nd batch) of light yellow solid. Two batches were combined, dried to afford 3.8 kg of Form I (m.p. at 133 °C) 5-(3,4-difluorobenzyl)-8-((1r,4r)-4-methylcyclohexyl)-6,9-dioxo-2,5,8-triazaspiro[3.5]nonane-2-carbaldehyde light yellow solid. The overall yield of this step is 97%.
PAT
- Cardiac sarcomere inhibitorsPublication Number: US-12286437-B2Priority Date: 2021-03-04Grant Date: 2025-04-29
- Cardiac sarcomere inhibitorsPublication Number: US-11919909-B2Priority Date: 2021-03-04Grant Date: 2024-03-05
- Cardiac sarcomere inhibitorsPublication Number: US-2024309011-A1Priority Date: 2021-03-04
- Cardiac sarcomere inhibitorsPublication Number: WO-2022187501-A1Priority Date: 2021-03-04
- Cardiac sarcomere inhibitorsPublication Number: US-2022306642-A1Priority Date: 2021-03-04
- cardiac sarcomere inhibitorPublication Number: CN-117083275-APriority Date: 2021-03-04
- Cardiac sarcomere inhibitorsPublication Number: EP-4301760-A1Priority Date: 2021-03-04
- Crystalline forms of 5-(3,4-difluorobenzyl)-8-((1r,4r)-4-methylcyclohexyl)-6,9-dioxo-2,5,8-triazaspiro[3.5]nonane-2-carbaldehydePublication Number: US-2024132498-A1Priority Date: 2022-09-02
- Crystalline forms of 5- (3, 4-difluorobenzyl) -8- ((1 r,4 r) -4-methylcyclohexyl) -6, 9-dioxo-2, 5, 8-triazaspiro [3.5] nonane-2-carbaldehydePublication Number: CN-119998292-APriority Date: 2022-09-02
- Crystalline forms of 5-(3,4-difluorobenzyl)-8-((1r,4r)-4-methylcyclohexyl)-6,9-dioxo-2,5,8-triazaspiro[3.5]nonane-2-carbaldehydePublication Number: WO-2024050539-A1Priority Date: 2022-09-02
- Crystalline forms of 5-(3,4-difluorobenzyl)-8-((1r,4r)-4-methylcyclohexyl)-6,9-dioxo-2,5,8-triazaspiro[3.5]nonane-2-carbaldehydePublication Number: EP-4581034-A1Priority Date: 2022-09-02
- Cardiac sarcomere inhibitorsPublication Number: TW-202302594-APriority Date: 2021-03-04
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REF
Publication Name: Scientific Reports
Publication Date: 2024-05-27
PMCID: PMC11130313
PMID: 38802475
DOI: 10.1038/s41598-024-62840-3
///////////////ulacamten, ANAX, cardiac myosin inhibitor, CK-586, CK-4021586, CK 586, CK 4021586, X325G97HZJ
Tigemocoxib
Tigemocoxib
MF C15H14ClF3O3 MW 334.72
2H-1-Benzopyran-3-carboxylic acid, 6-chloro-7-(1,1-dimethylethyl)-2-(trifluoromethyl)-, (2S)-
(2S)-7-tert-butyl-6-chloro-2-(trifluoromethyl)-2H-1-benzopyran-3-carboxylic acid
(2S)-7-tert-butyl-6-chloro-2-(trifluoromethyl)-2H-1-benzopyran-3-carboxylic acid
cyclo-oxygenase 2 (COX-2) inhibitor, anti-inflammatory, SC-75416, SC 75416, C8D42HX4WH
CAS 215122-74-0
Originator: Pfizer Inc.
Tigemocoxib is a small molecule drug. The usage of the INN stem ‘-coxib’ in the name indicates that Tigemocoxib is a selective cyclo-oxygenase inhibitor. Tigemocoxib has a monoisotopic molecular weight of 334.06 Da.
Tigemocoxib (also known as SC-75416) is a selective cyclo-oxygenase 2 (COX-2) inhibitor and nonsteroidal anti-inflammatory drug (NSAID) designed for reducing pain and inflammation. Initially developed as an orally bioavailable clinical lead for treating acute, postoperative, and chronic inflammatory pain, it acts by targeting the COX-2 enzyme
SYN
Bioorganic & Medicinal Chemistry LettersPublication Date: 2010-12-01PMID: 20709553DOI: 10.1016/j.bmcl.2010.07.054
PAT
WO2000037469
PAT
EXAMPLE 68
(S)-6-Chloro-7-(1,1-dimethylethyl)-2-(trifluoromethyl)-2H-1- benzopyran-3-carboxylic acid To a solution of 6-chloro-7-(1,1-dimethylethyl)-2-trifluoromethyl-2H-1-benzopyran-3-carboxylic acid (Example 8) (11.4 g, 34.1 mmol) and (S)-(-)-2-amino-3-phenyl-1-propanol (2.57 g, 17.00 mmol) was added n-heptane (200 mL) and the mixture set aside for 16 h. The resulting
suspension was filtered yielding a solid (3.8 g). This solid was recrystallized from 2-butanone (20 mL) and n-heptane (200 mL) yielding upon filtration a white solid (3.0 g).
This solid was dissolved in ethyl acetate (100 mL) and washed with 1 N hydrochloric acid (50 mL) and brine (2 × 50 mL), dried over MgSO4 and concentrated in vacuo yielding a white solid. This solid was recrystallized from n-heptane yielding the title compound of high optical purity as a crystalline solid (1.7 g, 30%): mp 175.4-176.9 °C. 1H NMR (acetone-d6/300 MHz) 7.86 (s, 1H), 7.52 (s, 1H), 7.12 (s,
1 H), 5.83 (q, 1H, J = 7.1 Hz), 1.48 (s, 9H). Anal. Calc’d for C15H14O3F3Cl : C, 53.83; H, 4.22; N, 0.0; Cl, 10.59. Found: C, 53.78; H, 4.20; N, 0.0; Cl, 10.65. This compound was determined to have an optical purity of greater than 90% ee. Chiral purity was determined as describe in Example 66.
EXAMPLE 8
6-Chloro-7-(1,1-dimethylethyl)-2-trifluoromethyl- 2H-1-benzopyran-3-carboxylic acid
Step 1. Preparation of 4-tert-butylsalicylaldehyde.
A five liter three-neck round bottom flask equipped with overhead mechanical stirrer and condenser was charged with trifluoroacetic acid (2.4 L). A mixture of 3-tert-butylphenol (412 g, 2.8 mole) and HMTA (424 g, 3.0 mole) was added portion-wise causing an exotherm. With cooling, the temperature was maintained under 80 °C. The reaction was heated at 80 °C for one hour, then cooled, and water (2 L) added. After 0.5 hour additional water (4 L) was added and the mixture was extracted with ethyl acetate (6 L). The organic extract was washed with water and brine. The resulting organic phase was divided into 2 L volumes and each diluted with water (1 L), and solid NaHCO3 added until the mixture was neutralized. The organic phases were isolated and combined, dried over MgSO4, filtered and
concentrated in vacuo yielding an oil. This oil was
distilled at 95 °C (0.8 mm) yielding the desired
salicylaldehyde as an oil (272.9 g, 56 %) which was of sufficient purity to be used without further purification.
Step 2. Preparation of ethyl 7-(1,1-dimethylethyl)-2- (trifluoromethyl)-2H-1-benzopyran-3-carboxylate.
A one liter three-neck flask was charged with 4-tert-butylsalicylaldehyde (Step 1) (100.0 g, 0.56 mole),
dimethylformamide (110 mL), and potassium carbonate (79.9 g, 0.58 mole) causing the temperature of the mixture to rise to 40 °C. Ethyl 4,4,4-trifluorocrotonate (118.0 g, 0.70 mole) in dimethylformamide (110 mL) was added and the mixture heated to 60 °C at which time the reaction temperature rose to 70 °C. The reaction was cooled to 60 °C, maintained at 60
°C (with addedheating) for 8.5 hours and cooled to room temperature. Ethyl acetate (600 mL) and 3 N HCl (600 mL) were added, mixed, and the layers separated. The aqueous phase was extracted with ethyl acetate and the organic phases were combined. The combined organic phases were washed with brine-water (1:1), brine, dried over MgSO4, filtered and concentrated in vacuo, yielding a semi-solid. Hexane (600 mL) was added with mixing and the mixture was filtered. The filtrate was washed with brine, dried over
MgSO4, filtered and concentrated in vacuo yielding a solid. This solid was dissolved in hot ethanol (600 mL). Water (190 mL) was added which induced crystallization. Filtration of the mixture and drying of the product provided the desired ester as a crystalline solid (131.3 g, 71%): mp 91.0-94.9 °C. This material was of suitable purity to be used in subsequent steps without further purification.
Step 3. Preparation of ethyl 6-chloro-7-(1,1-dimethylethyl)-2-(trifluoromethyl)-2H-1-benzopyran-3-carboxylate.
A one liter three-neck flask equipped with mechanical stirrer and gas inlet tube was charged with the ester (Step 2) (100 g, 0.3 mole) and acetic acid (300 mL). While cooling (water bath) the reaction mixture, chlorine gas (37.6 g, 0.53 mole) was added which caused the temperature to rise to 48 °C. After stirring for two hours, the
reaction was cooled in an ice-water bath to 15 °C. Zinc powder (19.5 g, 0.3 mole) was added in one portion which caused the temperature to rise to 72 °C. After cooling to room temperature additional zinc powder (5.0 g, 0.08 mole) was added and the mixture was stirred for 0.5 hour longer. The crude mixture was filtered through diatomaceous earth and was concentrated in vacuo yielding an oil. The oil was dissolved in ethyl acetate (700 mL) washed with brine-water (1:1, 1 L) and brine (0.5 L). The resulting aqueous phase was extracted with ethyl acetate (700 mL). This ethyl acetate phase was washed with brine-water (1:1, 1 L) and brine (0.5 L). The combined organic phases were dried over
MgSO4, filtered and concentrated in vacuo yielding the title compound as a yellow oil (116 g, 106 %). This material, which contained some entrained ethyl acetate, was of suitable purity to be used in subsequent steps without further purification.
Step 4. Preparation of 6-chloro-7-(1,1-dimethylethyl)-2- (trifluoromethyl)-2H-1-benzopyran-3-carboxylic acid.
To a solution of the ester (Step 3) (116 g,
0.3 mole) in methanol (500 mL) and tetrahydrofuran (500 mL) in a one liter flask was added aqueous
sodium hydroxide (2.5 N, 240 mL, 0.6 mole). After
stirring overnight, the pH of the solution was
adjusted to 1 with concentrated hydrochloric acid
and the solution was extracted with ethyl acetate.
The ethyl acetate phase was dried over MgSO4,
filtered and concentrated in vacuo yielding a
solid. This solid was dissolved in hot ethanol
(500 mL). Water (500 mL) was added and upon
cooling to room temperature crystals formed which
were collected by vacuum filtration. The crystals
were washed with ethanol-water (3:7, 3 X 200 mL)
and dried providing the title acid as a
crystalline solid (91.6 g, 91 %) : mp 194.9-196.5
°C. 1H NMR (acetone-d6/300 MHz) 7.86 (s, 1H),
7.52 (s, 1H), 7.12 (s, 1H), 5.83 (q, 1H, J = 7.1
Hz), 1.48 (s, 9H). Anal. Calc’d for C15H14ClF3O3:
C, 53.83; H, 4.22; Cl, 10.59. Found: C, 53.92; H,
4.24; Cl, 10.50
REF
- The IUPHAR Guide to Immunopharmacology: connecting immunology and pharmacologyPublication Name: ImmunologyPublication Date: 2020-03-02PMCID: PMC7160657PMID: 32020584DOI: 10.1111/imm.13175
- Synthesis of Deuterated Benzopyran Derivatives as Selective COX-2 Inhibitors with Improved Pharmacokinetic PropertiesPublication Name: ACS Medicinal Chemistry LettersPublication Date: 2014-08-06PMCID: PMC4190635PMID: 25313331DOI: 10.1021/ml500299q
- Leukotrienes, But Not Angiotensin II, Are Involved in the Renal Effects Elicited by the Prolonged Cyclooxygenase-2 Inhibition When Sodium Intake Is LowPublication Name: Journal of Cardiovascular PharmacologyPublication Date: 2013-04PMID: 23288201DOI: 10.1097/fjc.0b013e31828399ae
- The novel benzopyran class of selective cyclooxygenase-2 inhibitors. Part 2: The second clinical candidate having a shorter and favorable human half-lifePublication Name: Bioorganic & Medicinal Chemistry LettersPublication Date: 2010-12-01PMID: 20709553DOI: 10.1016/j.bmcl.2010.07.054
- Evaluation of COX-1/COX-2 selectivity and potency of a new class of COX-2 inhibitorsPublication Name: European Journal of PharmacologyPublication Date: 2008-06-24PMID: 18457826DOI: 10.1016/j.ejphar.2008.03.057
- Modeling and Simulation to Support Dose Selection and Clinical Development of SC-75416, a Selective COX-2 Inhibitor for the Treatment of Acute and Chronic Pain
- Publication Name: Clinical pharmacology and therapeutics
- Publication Date: 2007-09-19
- PMID: 17882158
- DOI: 10.1038/sj.clpt.6100374
PAT
- Substituted benzopyran derivatives for the treatment of inflammationPublication Number: EP-0977748-A1Priority Date: 1997-04-21
- Endothermic reaction apparatusPublication Number: NO-308725-B1Priority Date: 1993-06-16
- History of Transformed Benzofiran, their preparation and pharmacological preparations for the treatment of inflammation containing themPublication Number: IL-132296-APriority Date: 1997-04-21
- Substituted benzopyran derivatives for the treatment of inflammationPublication Number: KR-100538258-B1Priority Date: 1997-04-21Grant Date: 2006-01-12
- Substituted benzopyran derivatives for the treatmentPublication Number: US-6806288-B1Priority Date: 1997-04-21Grant Date: 2004-10-19
- Benzopyran derivatives with substituents for the treatment of inflammationPublication Number: JP-4577534-B2Priority Date: 1997-04-21Grant Date: 2010-11-10
- Substituted benzopyran derivatives for the treatment of inflammationPublication Number: KR-20010020152-APriority Date: 1997-04-21
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///////////tigemocoxib, ANAX, cyclo-oxygenase 2 (COX-2) inhibitor, anti-inflammatory, SC-75416, SC 75416, C8D42HX4WH
Teprosulvose
Teprosulvose
CAS 1983131-47-0
MF C27H52O10S MW568.761
| Sulfoquynovosylacylpropanediol [(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(3-octadecanoyloxypropoxy)oxan-2-yl]methanesulfonic acid |
3-(octadecanoyloxy)propyl 6-deoxy-6-sulfo-α-D-glucopyranoside
radiosensitizer (veterinary use), WV7377RGM8, SQAP
Teprosulvose (CAS 1983131-47-0) is a novel synthetic glycolipid, specifically a sulfoquinovosylacylpropanediol (SQAP). It is primarily developed for use in veterinary medicine as a radiosensitizer, intended to enhance the effectiveness of radiation therapy in treating malignant tumors.
1. Chemical Identity and Structure
- USAN/INN Name: Teprosulvose
- Systemic Name: 3-(octadecanoyloxy)propyl 6-deoxy-6-sulfo-$\alpha$-D-glucopyranoside
- Molecular Weight: 568.76 g/mol
- Structure: It consists of a glucose derivative (6-deoxy-6-sulfo-$\alpha$-D-glucopyranoside) linked via a propyl bridge to a long-chain fatty acid (stearic acid/octadecanoic acid).
Regulatory Data
Teprosulvose is currently in the investigational stage, primarily focused on veterinary oncology.
- USAN/INN Status: The name “Teprosulvose” was officially adopted by the USAN Council in 2024 (File LM-156).
- Classification: Radiosensitizer.
- Target Application: Adjuvant therapy for malignant tumors in animals (e.g., canine or feline cancers).
- Current Status: It has not yet received full FDA or EMA approval for human use. In the U.S., it is typically handled under Investigational New Animal Drug (INAD) protocols for clinical trials in veterinary patients.
Note: Because it is a specialized veterinary investigative agent, detailed safety data (LD50, pharmacokinetics) is generally found in specific FDA Freedom of Information (FOI) summaries or peer-reviewed veterinary oncology journals rather than standard human drug databases.
INN List 131 (WHO): Teprosulvose was officially included in the World Health Organization’s International Nonproprietary Names (INN) list in 2024. This confirms its unique status as a distinct drug substance.
USAN Council: The United States Adopted Names Council assigned the name in 2024, classifying it as a radiosensitizer.
FDA Status: It is currently under investigation (INAD) for canine oral melanoma and other solid tumors in veterinary medicine. Human clinical trial data is not yet widely available as the primary focus remains on the “Veterinary First” pathway.
Mechanism of Action: It is a potent inhibitor of DNA polymerase $\alpha$ and $\beta$. By inhibiting the repair of radiation-induced DNA damage, it effectively “locks in” the damage to tumor cells while sparing normal tissue due to differential uptake.
PAT
US Patent 10,206,942 (and related continuations): Covers the use of SQAP compounds in combination with radiation.
WO 2017/023812: International filing regarding the composition and therapeutic application of these glycolipids.
PAT
PAT
- Sulfonated sugar compounds, pharmaceutical compositions which contain the same, and methods of treating tumors with the samePublication Number: US-7973145-B2Priority Date: 2007-07-20Grant Date: 2011-07-05
- Sulfonated sugar compounds, pharmaceutical compositions which contain the same, and methods of treating tumors with the samePublication Number: US-2009209475-A1Priority Date: 2007-07-20
- Novel sulfonated sugar derivative, and use thereof for medicinal agentPublication Number: EP-2130834-A1Priority Date: 2007-07-20
- Sulfonated sugar compounds, pharmaceutical compositions which contain the same, and methods of treating tumors with the samePublication Number: US-2010298246-A1Priority Date: 2007-07-20
- Novel sulfonated sugar derivatives and their use as pharmaceuticalsPublication Number: JP-4435861-B2Priority Date: 2007-07-20Grant Date: 2010-03-24
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//////////teprosulvose, radiosensitizer (veterinary use), WV7377RGM8, SQAP
Suricapavir
Suricapavir
CAS 2417270-21-2
MF C41H29ClF9N9O4S MF950.2 g/mol
N-[(1S)-1-[3-[4-chloro-3-(methanesulfonamido)-1-methylindazol-7-yl]-4-oxo-7-[6-(trifluoromethyl)-2-pyridinyl]quinazolin-2-yl]-2-(3,5-difluorophenyl)ethyl]-2-[(2S,4R)-9-(difluoromethyl)-5,5-difluoro-7,8-diazatricyclo[4.3.0.02,4]nona-1(6),8-dien-7-yl]acetamide
N-[(1S)-1-[3-[4-chloro-3-(methanesulfonamido)-1-methyl-indazol-7-yl]-4-oxo-7-[6-(trifluoromethyl)-2-pyridyl]quinazolin-2-yl]-2-(3,5-difluorophenyl)ethyl]-2-[(2S,4R)-9-(difluoromethyl)-5,5-difluoro-7,8-diazatricyclo[4.3.0.02,4]nona-1(6),8-dien-7-yl]acetamide
N-[(1S)-1-{(3P)-3-[4-chloro-3-(methanesulfonamido)-1-methyl-1Hindazol-7-yl]-4-oxo-7-[6-(trifluoromethyl)pyridin-2-yl]-3,4-
dihydroquinazolin-2-yl}-2-(3,5-difluorophenyl)ethyl]-2-[(3bS,4aR)-3-
(difluoromethyl)-5,5-difluoro-3b,4,4a,5-tetrahydro-1Hcyclopropa[3,4]cyclopenta[1,2-c]pyrazol-1-yl]acetamide
inhibitor of viral replication, antiviral, ZZ799EX5KN
tructurally resembles:
- Lenacapavir-type macroheterocyclic capsid inhibitors (Gilead class)
PAT
Preparation of Example 59: N-((S)-1-((3P)-3-(4-chloro-1-methyl-3-(methylsulfonamido)-1H-indazol-7-yl)-4-oxo-7-(6-(trifluoromethyl)pyridin-2-yl)-3,4-dihydroquinazolin-2-yl)-2- (3,5-difluorophenyl)ethyl)-2-((3bS,4aR)-3-(difluoromethyl)-5,5-difluoro-3b,4,4a,5- tetrahydro-1H-cyclopropa[3,4]cyclopenta[1,2-c]pyrazol-1-yl)acetamide.
The title compound was prepared according to General Procedure D using 2-chloro-6-(trifluoromethyl)pyridine as the coupling partner. The experiment afforded the title compound, N-((S)-1-((3P)-3-(4-chloro-1-methyl-3-(methylsulfonamido)-1H-indazol-7-yl)-4-oxo-7-(6-(trifluoromethyl)pyridin-2-yl)-3,4-dihydroquinazolin-2-yl)-2-(3,5-difluorophenyl)ethyl)-2-((3bS,4aR)-3-(difluoromethyl)-5,5-difluoro-3b,4,4a,5-tetrahydro-1H-cyclopropa[3,4]cyclopenta[1,2-c]pyrazol-1-yl)acetamide. The sample was analyzed using LCMS Method F: retention time = 1.51 min.; observed ion = 948.4 (M-H).1H NMR (METHANOL-d4, 500 MHz) Shift 8.66 (s, 1H), 8.4-8.4 (m, 3H), 8.22 (t, 1H, J=7.9 Hz), 7.88 (d, 1H, J=7.7 Hz), 7.28 (br d, 1H, J=8.0 Hz), 7.20 (d, 1H, J=7.7 Hz), 6.7-6.8 (m, 1H), 6.61 (dd, 2H, J=2.2, 8.2 Hz), 6.67 (br t, 2H, J=54.7 Hz), 4.5-4.6 (m, 2H), 3.61 (s, 3H), 3.4-3.5 (m, 1H), 3.2-3.2 (m, 3H), 3.1-3.2 (m, 1H), 2.41 (br dd, 2H, J=3.7, 7.3 Hz), 1.34 (br d, 1H, J=5.4 Hz), 0.99 (br dd, 1H, J=1.9, 3.7 Hz)
PAT
WO 2020/084492 and WO 2020/254985 disclose certain Capsid Inhibitor compounds including the two compounds shown below which will be referred to in this application as the compounds of Formula la and Formula lb.
PAT
- Inhibitors of human immunodeficiency virus replicationPublication Number: WO-2023062559-A1Priority Date: 2021-10-13
- Inhibitors of human immunodeficiency virus replicationPublication Number: US-2023149408-A1Priority Date: 2020-04-15
- Inhibitors of human immunodeficiency virus replicationPublication Number: WO-2021209900-A1Priority Date: 2020-04-15
- Pharmaceutical compositions comprising cabotegravirPublication Number: US-2023045509-A1Priority Date: 2019-12-09
- Inhibitors of human immunodeficiency virus replicationPublication Number: US-11541055-B2Priority Date: 2018-10-24Grant Date: 2023-01-03
- Inhibitors of human immunodeficiency virus replicationPublication Number: US-2020360384-A1Priority Date: 2018-10-24
- Inhibitors of human immunodeficiency virus replicationPublication Number: EP-3870577-B1Priority Date: 2018-10-24Grant Date: 2025-03-19
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///////////////suricapavir, ANAX, inhibitor of viral replication, antiviral, ZZ799EX5KN
Soxataltinib
Soxataltinib
CAS 2546116-88-3
MF C29H30N8O2 MW 522.60
6-(3-hydroxy-3-methylazetidin-1-yl)-4-(6-{6-[(6-methoxypyridin-3-yl)methyl]-3,6-diazabicyclo[3.1.1]heptan-3-yl}pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carbonitrile
| Pyrazolo[1,5-a]pyridine-3-carbonitrile, 6-(3-hydroxy-3-methyl-1-azetidinyl)-4-[6-[6-[(6-methoxy-3-pyridinyl)methyl]-3,6-diazabicyclo[3.1.1]hept-3-yl]-3-pyridinyl]- |
6-(3-hydroxy-3-methylazetidin-1-yl)-4-(6-{6-[(6-methoxypyridin-3-yl)methyl]-3,6-diazabicyclo[3.1.1]heptan-3-yl}pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carbonitrile
RET-kinase inhibitor, antineoplastic, HS-10365, HS 10365, AZ4Q643U3D
Soxataltinib (example 7) is a potent inhibitor of RET-kinase , with the IC 50of 0.601 nM. Soxataltinib plays an important role in
cancer research.
Discovery and Development
- Soxataltinib corresponds to Example 114 in a patent [WO2020228756]describing pyrazolo[1,5-a]pyridine carbonitrile RET inhibitors.
- It is believed to correspond to HS-10365, a RET inhibitor developed by Hansoh Pharma (structure disclosed via patent).
Drug class comparison:
| Drug | Company | Type |
|---|---|---|
| Selpercatinib | Eli Lilly | 1st-gen selective RET inhibitor |
| Pralsetinib | Blueprint | selective RET inhibitor |
| Soxataltinib | Hansoh | next-gen RET inhibitor |
Patent Family (Major Members)
Typical family members include:
| Patent | Jurisdiction |
|---|---|
| WO2020228756 | WIPO |
| CN112209925 | China |
| US continuation filings | USA |
| EP equivalents | Europe |
One Chinese patent describes the preparation of piperazine-containing pyrazolopyridine RET inhibitors, including Soxataltinib analogues
SYN
SYN
Example 32
| To a 25 mL sealed tube were added successively 49 (52 mg, 0.1 mmol), Pd 2(dba) 3 (5.5 mg, 0.006 mmol), t-BuXPhos (8.4 mg, 0.02 mmol), 3-methyl-3-azetidinol (26 mg, 0.3 mmol), Cs 2CO 3 (65 mg, 0.2 mmol), 1,4-dioxane (3 mL) and DMF (1 mL). The mixture was stirred at 80° C. overnight under Ar, and TLC monitoring showed no starting material 49 remained. The mixture was cooled to room temperature, and 10 mL of water was added. The mixture was stirred for 10 min, and a yellow solid precipitated. The solid was collected by filtration, dried and purified by column chromatography to give product 86 (34 mg, 65% yield). |
SYN
[1913]6-(3-hydroxy-3-methylacetidin-1-yl)-4-(6-(6-((6-methoxypyridin-3-yl)methyl)-3,6-diazabicyclo[3.1.1]heptane-3-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-carboxynitrile
Using 3-methylacetidin-3-ol as a raw material, in the first step of Reference Example 110, 6-(3-hydroxy-3-methylacetidin-1-yl)-4-(6-(6-((6-methoxypyridin-3-yl)methyl)-3,6-diazabicyclo[3.1.1]heptane-3-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-carboxynitrile was obtained.
[1916]MS m/z(ESI):523.3[M+H]
[1917]
1H NMR(400MHz,CDCl 3)δ8.40(s,1H),8.15(s,3H),7.82(d,J＝7.4Hz,1H),7.74(s,1H),6.80(d,J＝8.4Hz,1H),6.75(d,J＝1.7Hz,1H),6.72(d,J＝8.8Hz,1H),4.21(s,2H),4.01(s,2H),3.93-3.92(m,7H),3.84(d,J＝7.3Hz,4H),1.68(s,3H).
PAT
- Inhibitor containing dihecyclic derivatives, its preparation method and applicationPublication Number: CN-112368283-BPriority Date: 2019-05-14Grant Date: 2023-02-17
- Inhibitor containing dihecyclic derivatives, its preparation method and applicationPublication Number: CN-115974897-APriority Date: 2019-05-14
- Inhibitor containing dihecyclic derivatives, its preparation method and applicationPublication Number: CN-116444515-APriority Date: 2019-05-14
- Inhibitor containing bicyclic derivative, preparation method therefor and use thereofPublication Number: WO-2020228756-A1Priority Date: 2019-05-14
- Inhibitor containing bicyclic derivative, preparation method therefor and use thereofPublication Number: EP-3971187-B1Priority Date: 2019-05-14Grant Date: 2025-05-07
- Ret selective inhibitor, preparation method therefor and use thereofPublication Number: WO-2021008455-A1Priority Date: 2019-07-12
- RET selective inhibitor and preparation method and use thereofPublication Number: CN-112209925-APriority Date: 2019-07-12
- RET selective inhibitors and methods for their preparation and usePublication Number: KR-102735956-B1Priority Date: 2019-07-12Grant Date: 2024-11-28
- RET selective inhibitors and preparation methods and uses thereofPublication Number: CN-114072404-BPriority Date: 2019-07-12Grant Date: 2023-09-15
- Inhibitor containing bicyclic derivative, preparation method therefor and use thereofPublication Number: US-2022259201-A1Priority Date: 2019-05-14
- Heteroaromatic ring compound as ret kinase inhibitor, and preparation and use thereofPublication Number: US-2023322769-A1Priority Date: 2020-08-20
- 3,6 diazabicyclo[3.1.1]heptane derivatives as RET kinase inhibitorsPublication Number: CN-112778337-BPriority Date: 2019-11-08Grant Date: 2023-09-26
- Ret selective inhibitor, preparation method therefor and use thereofPublication Number: EP-3998265-A1Priority Date: 2019-07-12
- RET selective inhibitor and preparation method and use thereofPublication Number: CN-117865952-APriority Date: 2019-07-12
- Ret selective inhibitor, preparation method therefor and use thereofPublication Number: US-2022289740-A1Priority Date: 2019-07-12
- Crystal form of free base of inhibitor containing bicyclic ring derivative and preparation method and application of crystal formPublication Number: US-2023406865-A1Priority Date: 2020-11-13
- Crystal form of free base of inhibitor containing bicyclic ring derivative and preparation method and application of crystal formPublication Number: EP-4245757-A1Priority Date: 2020-11-13
- Crystal form of free base of inhibitor containing bicyclic ring derivative and preparation method and application of crystal formPublication Number: WO-2022100738-A1Priority Date: 2020-11-13
- Crystal form of inhibitor free base including bicyclic derivatives, preparation method and use thereofPublication Number: KR-20230107271-APriority Date: 2020-11-13
- Heteroaromatic ring compound as ret kinase inhibitor, and preparation and use thereofPublication Number: EP-4201936-A1Priority Date: 2020-08-20
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/////////soxataltinib, ANAX, RET-kinase inhibitor, antineoplastic, HS-10365, HS 10365, AZ4Q643U3D
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Selonabant
Selonabant
CAS 791848-71-0
MF C22H24ClF3N2O2 MW440.89 g/mol
N–tert-butyl-3-[(R)-(4-chlorophenyl)-[2-(trifluoromethyl)phenyl]methoxy]azetidine-1-carboxamide
N-tert-butyl-3-[(R)-(4-chlorophenyl)-[2-(trifluoromethyl)phenyl]methoxy]azetidine-1-carboxamide
(R)-N-(tert-butyl)-3-((4-chlorophenyl)(2-(trifluoromethyl)phenyl)methoxy)azetidine-1-carboxamide
N-tert-butyl-3-{(R)-(4-chlorophenyl)[2-(trifluoromethyl)phenyl]methoxy}azetidine-1-carboxamide
cannabinoid receptor 1 (CB1) antagonist, ANEB 001, V 24343, 4RNU8C6XXW, ANEB001
Drug class: Cannabinoid receptor antagonist (CB1)
The anti-obesity drug, V24343, acts by targeting the CB1 receptor in the brain and suppressing a person’s appetite.
Selonabant (INNTooltip International Nonproprietary Name, USANTooltip United States Adopted Name; developmental code names ANEB-001, V-24343) is a cannabinoid CB1 receptor antagonist which is under development for the treatment of acute cannabinoid intoxication.[1][2][3] It was also previously being developed to treat obesity, but development for this indication was discontinued.[1] The drug is administered by intravenous infusion.[1] It dramatically reduced the subjective effects of Δ9-tetrahydrocannabinol (THC) in a clinical trial.[3] Selonabant is being developed by Vernalis and Anebulo Pharmaceuticals.[1][2]
1 CLINICAL TRIALS
As of December 2024, it is in phase 2 trials.[1][2], I.V. Selonabant in Healthy Adult SubjectsCTID: NCT07211607Phase: Phase 1Status: RecruitingDate: 2026-02-12
Safety, Tolerability, Pharmacokinetics, and Pharmacodynamics of CB1 Antagonist ANEB-001 in a THC Challenge TestCTID: NCT05282797Phase: Phase 2Status: CompletedDate: 2023-08-29
Safety and Efficacy of Low Doses of V24343 in Obese SubjectsCTID: NCT00734201Phase: Phase 1Status: CompletedDate: 2011-07-25
A randomized, double-blind, placebo-controlled study to assess the safety, tolerability, pharmacokinetics and pharmacodynamics of single oral doses of CB1 antagonist ANEB-001 in healthy occasional cannabis users
EudraCT: 2021-000305-24
Phase: Phase 2, Status: Completed, Date: 2021-03-18
2. Chemical Structure Features
Key structural motifs:
• Azetidine ring (4-membered nitrogen heterocycle)
• Chiral benzhydryl ether center
• Trifluoromethyl phenyl group
• p-chlorophenyl group
• tert-butyl carboxamide
These motifs are typical of lipophilic GPCR ligands, enabling strong binding to the CB1 receptor.
Key descriptors:
| Property | Value |
|---|---|
| LogP | ~4.9 |
| H-bond donors | 1 |
| H-bond acceptors | 5 |
| TPSA | 41.6 Ų |
| Chiral centers | 1 |
3. Pharmacological Target
Primary target:
CB1 receptor (CNR1)
• GPCR located in the central nervous system
• Mediates effects of cannabinoids such as THC
Selonabant is a competitive CB1 antagonist.
Mechanism:
- THC activates CB1 receptor
- Leads to euphoria, altered cognition, tachycardia
- Selonabant blocks CB1 binding
- Reverses or prevents THC effects
4. Therapeutic Indication
Main indication
Acute cannabinoid intoxication
Potential clinical uses:
• Cannabis overdose in emergency rooms
• Pediatric accidental cannabis ingestion
• Edible THC overdose
• Severe psychiatric reactions to cannabis
A CB1 antagonist could act as a “cannabis antidote.”
5. Clinical Development
Developer:
Anebulo Pharmaceuticals (with earlier work by Vernalis)
Development timeline
| Phase | Details |
|---|---|
| Preclinical | Demonstrated CB1 antagonism |
| Phase I | Safety and PK studies |
| Phase II | THC challenge studies |
In clinical trials, the drug significantly reduced subjective effects of THC in volunteers.
Status (2024–2025): Phase II development.
6. Administration
Originally studied as:
• Intravenous infusion for rapid reversal of THC effects
Some reports indicate oral activity in research settings.
The IV route is preferred in emergency settings.
7. Comparison with Earlier CB1 Antagonists
Selonabant belongs to the same pharmacological class as:
| Drug | Status |
|---|---|
| Rimonabant | Withdrawn (psychiatric side effects) |
| Taranabant | Development stopped |
| Selonabant | Designed for short-term antidote use |
Key difference:
Earlier CB1 antagonists were chronic obesity drugs, which caused depression and suicidality.
Selonabant is designed for acute use only, reducing psychiatric risk.
8. Pharmacological Profile
Approximate characteristics (reported in literature):
• High CB1 receptor affinity
• CNS-penetrant
• Rapid onset
• Short therapeutic exposure
Effects in THC challenge studies:
• Reduced intoxication score
• Reduced cognitive impairment
• Reduced subjective “high”
9. Chemical Class
Selonabant can be classified as:
Diarylmethoxy-azetidine carbamides
Key scaffold:
Diarylmethanol → ether → azetidine carbamate.
This scaffold appears in several CB1 inverse agonists.
PATENT
WO2005080345
Title: Cannabinoid CB1 receptor antagonists
Assignee: Vernalis (R&D) Ltd
Priority: ~2004
This is the primary patent family covering the scaffold used for Selonabant.
Related Continuation Patent
WO2005080328
Follow-up Patent on CB1 Antagonists
WO2005075450
Later Use Patent (Anebulo)
US11141404
Assignee: Anebulo Pharmaceuticals
Coverage:
• use of Selonabant (ANEB-001)
• treatment of acute cannabinoid overdose
• IV formulations
The patent protection extends to ~2040
Patent Family Map
Main Selonabant IP family:
| Patent | Type | Notes |
|---|---|---|
| WO2005080345 | Composition of matter | core scaffold |
| WO2005080328 | analog compounds | synthetic examples |
| WO2005075450 | optimized CB1 antagonists | SAR |
| US11141404 | method of use | overdose treatment |
| PCT follow-ups | formulation / delivery | IV use |
SYN
https://patents.google.com/patent/US11141404B1/en
SYN
US 7,504,522
Preparation of 2-(trifluoromethyl)-4-chlorobenzhydrol (96)
Preparation of 1-benzhydryl-3-[2-(trifluoromethyl)-4′-chlorobenzhydryloxy]azetidine (97)
| This material was prepared from 1-benzhydryl-3-azetidinol (1) (40.1 mmol) and 2-(trifluoromethyl)-4-chlorobenzhydrol (96) (80.2 mmol) using the procedure described for compound (3) (13.5 g, 66%). |
Preparation of 3-[2-(trifluoromethyl)-4′-chlorobenzhydryloxy]azetidine hydrochloride (98)
| This material was prepared from 1-benzhydryl-3-[2-(trifluoromethyl)-4′-chlorobenzhydryloxy]azetidine (97) (25.6 mmol) using the procedure described for compound (9) (8.2 g, 85%). |
| NMR (400 MHz, d 6-DMSO) δ H 3.78 (1H, m), 3.97 (3H, m), 4.89 (1H, q, J 6.0 Hz), 5.85 (1H, s), 7.33 (2H, m), 7.44 (2H, m), 7.59 (1H, m), 7.76 (3H, m), 8.97 (1H, bs) |
Example 81 FINAL MOLECULE
3-[2-(trifluoromethyl)-4′-chlorobenzhydryloxy]-N-(tert-butyl)azetidine-1-carboxamide (99)
| NMR (400 MHz, d 6-DMSO) δ H 1.20 (9H, s), 3.51 (1H, m), 3.65 (1H, m), 3.84 (2H, m), 4.25 (1H, m), 5.62 (1H, s), 5.73 (1H, s), 7.31 (2H, m), 7.39 (2H, m), 7.57 (1H, m), 7.75 (3H, m) |
SYN
(R)-N-(tert-butyl)-3-((4-chlorophenyl)(2-(trifluoromethyl)phenyl)methoxy)azetidine-1-carboxamide (Compound 1):
SYN
PAT
The core patent describing the chemistry for Selonabant-type molecules is:
WO2005080345
Title: Cannabinoid receptor antagonists
Assignee: Vernalis plc
Priority: ~2004
for SAR exploration
PATENTS
- Azetidinecarboxamide derivatives and their use in the treatment of cb1 receptor mediated disordersPublication Number: WO-2004096763-A1Priority Date: 2003-05-01
- Azetidinecarboxamide derivatives and their use in the treatment of CB1 receptor mediated disordersPublication Number: NZ-543016-APriority Date: 2003-05-01
- Botulinum neurotoxins for use in therapyPublication Number: US-11260114-B2Priority Date: 2017-03-22Grant Date: 2022-03-01
- Azetidinecarboxamide derivatives and their use in the treatment of cb1 receptor mediated disordersPublication Number: EP-1620395-A1Priority Date: 2003-05-01
- Azetidinecarboxamide derivatives and their use in the treatment of cb1 receptor mediated disordersPublication Number: EP-1620395-B1Priority Date: 2003-05-01Grant Date: 2009-12-30
- Azetidinecarboxamide derivatives and their use in the treatment of cb1 receptor mediated disordersPublication Number: US-7504522-B2Priority Date: 2003-05-01Grant Date: 2009-03-17
- Azetidinecarboxamide derivatives and their use in the treatment of cb1 receptor mediated disordersPublication Number: US-2007054891-A1Priority Date: 2003-05-01
- Botulinum neurotoxins production methodsPublication Number: US-2023016041-A1Priority Date: 2017-04-28
- Initiating neurotoxin treatmentsPublication Number: US-2023058666-A1Priority Date: 2017-04-21
- Initiating neurotoxin treatmentsPublication Number: EP-4137149-A1Priority Date: 2017-04-21
- Botulinum neurotoxins for treating hyperhidrosisPublication Number: US-2022370574-A1Priority Date: 2017-04-20
- Botulinum neurotoxins for use in therapyPublication Number: US-2023027850-A1Priority Date: 2017-03-22
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| Clinical data | |
|---|---|
| Other names | ANEB-001; ANEB001; V-24343; V24343 |
| Drug class | Cannabinoid receptor antagonist; Cannabinoid CB1 receptor antagonist; Cannabinoid antidote |
| Identifiers | |
| IUPAC name | |
| CAS Number | 791848-71-0 |
| PubChem CID | 68902536 |
| DrugBank | DB18908 |
| ChemSpider | 128922145 |
| UNII | 4RNU8C6XXW |
| KEGG | D12875 |
| ChEMBL | ChEMBL5095165 |
| Chemical and physical data | |
| Formula | C22H24ClF3N2O2 |
| Molar mass | 440.89 g·mol−1 |
| 3D model (JSmol) | Interactive image |
| SMILES | |
| InChI | |
References
- “Anebulo Pharmaceuticals”. AdisInsight. 26 December 2024. Retrieved 25 February 2025.
- “Delving into the Latest Updates on Selonabant with Synapse”. Synapse. 23 January 2025. Retrieved 25 February 2025.
- Gorbenko AA, Heuberger JA, Juachon M, Klaassen E, Tagen M, Lawler JF, et al. (February 2025). “CB1 Receptor Antagonist Selonabant (ANEB-001) Blocks Acute THC Effects in Healthy Volunteers: A Phase II Randomized Controlled Trial”. Clinical Pharmacology and Therapeutics. 117 (5): 1427–1436. doi:10.1002/cpt.3581. PMC 11993283. PMID 39898464.
//////////selonabant, cannabinoid receptor 1 (CB1) antagonist, ANEB 001, V 24343, 4RNU8C6XXW, ANEB001
Rosolutamide
Rosolutamide
CAS 1039760-91-2
MF C28H32O6 MW464.5 g/mol
(1E,6E)-4-(cyclobutylmethyl)-1,7-bis(3,4-dimethoxyphenyl)hepta-1,6-diene-3,5-dione
(1E,6E)-4-(cyclobutylmethyl)-1,7-bis(3,4-dimethoxyphenyl)hepta-1,6-diene-3,5-dione
antiandrogen, ASC-JM-17, ASC-JM17, JM17, ALZ-003, ALZ003, 5VLL140BN9,
Rosolutamide (INNTooltip International Nonproprietary Name; developmental code name ASC-JM17, JM17, ALZ-003) is an agonist of nuclear respiratory factor 1 (NRF1), a nonsteroidal antiandrogen, and an androgen receptor degrader related to curcumin.[1][2][3][4][5] Other analogues like dimethylcurcumin (ASC-J9) are also known.[2][6]
3-hydroxy imidacloprid is an imidacloprid. It has a role as a neonicotinoid insectide and a nicotinic acetylcholine receptor agonist.
REF
- Ferroptosis-related small-molecule compounds in cancer therapy: Strategies and applicationsPublication Name: European Journal of Medicinal ChemistryPublication Date: 2022-12-15PMID: 36332549DOI: 10.1016/j.ejmech.2022.114861
- A small-molecule Nrf1 and Nrf2 activator mitigates polyglutamine toxicity in spinal and bulbar muscular atrophyPublication Name: Human Molecular GeneticsPublication Date: 2016-03-08PMCID: PMC5062587PMID: 26962150DOI: 10.1093/hmg/ddw073
SYN
SYN
SYN
COMPD B
SYN
SYN
PAT
Publication Number: EP-2104659-B1
Priority Date: 2007-01-08
Grant Date: 2015-07-29
- Compounds with (1e, 6e)-1,7-bis-(3,4-dimethoxyphenyl)-4-4-disubstituted-hepta-1,6-diene-3,5-dione structural scaffold, their biological activity, and uses thereofPublication Number: US-2016264539-A1Priority Date: 2007-01-08
- Compounds with (substituted phenyl)-propenal moiety, their derivatives, biological activity, and uses thereofPublication Number: DK-2104659-T3Priority Date: 2007-01-08Grant Date: 2015-11-02
- Compounds with (1E, 6E)-1,7-Bis-(3,4-dimethoxyphenyl)-4-4-distributed-hepta-1,6-diene-3,5-dione structural scaffold, their biological activity, and uses thereofPublication Number: US-9562025-B2Priority Date: 2007-01-08Grant Date: 2017-02-07
- Compounds with (1E, 6E)-1,7-bis-(3,4-dimethoxyphenyl)-4,4-disubstituted-hepta-1,6-diene-3,5-dione structural scaffold, their biological activity, and uses thereofPublication Number: US-9000222-B2Priority Date: 2007-01-08Grant Date: 2015-04-07
- Compounds with (1 E, 6E)-1,7-bis-(3,4-dimethoxyphenyI)-4,4-disubstituted-hepta-1,6-diene-3,5-dione structural scaffold, their biological activity, and uses thereofPublication Number: US-9259402-B2Priority Date: 2007-01-08Grant Date: 2016-02-16
- Compounds with (1 E, 6E)-1,7-bis-(3,4-dimethoxyphenyl)-4,4-disubstituted-hepta-1,6-diene-3,5-dione structural scaffold, their biological activity, and uses thereofPublication Number: US-8710272-B2Priority Date: 2007-01-08Grant Date: 2014-04-29
- Compounds with (substituted phenyl)-propenal moiety, their derivatives, biological activity, and use thereofPublication Number: EP-2993165-A2Priority Date: 2007-01-08
- Compounds with (substituted phenyl)-propenal moiety, their derivatives, biological activity, and use thereofPublication Number: EP-2993165-B1Priority Date: 2007-01-08Grant Date: 2018-06-27
- Compounds with (1E, 6E)-1,7-bis-(3,4-dimethoxyphenyl)-4,4-disubstituted-hepta-1,6-diene-3,5-dione structural scaffold, their biological activity, and uses thereofPublication Number: US-2013261121-A1Priority Date: 2007-01-08
- Compounds with (substituted phenyl)-propenal moiety, their derivatives, biological activity, and uses thereofPublication Number: CA-2674780-CPriority Date: 2007-01-08Grant Date: 2014-03-11
- Compositions including androgen receptor degradation (ard) enhancers and methods of prophylactic or therapeutic treatment of skin disorders and hair lossPublication Number: CA-2694953-CPriority Date: 2007-07-31Grant Date: 2015-12-01
- Compositions containing androgen receptor degradation enhancers and methods for preventing or treating hair loss and skin diseasesPublication Number: KR-20100051808-APriority Date: 2007-07-31
- Compositions containing androgen receptor degradation (ARD) enhancers and methods for the prophylactic or therapeutic treatment of skin diseases and hair lossPublication Number: JP-2010535213-APriority Date: 2007-07-31
- Compounds with (1E, 6E)-1,7-bis-(3,4-dimethoxyphenyl)-4,4-disubstituted-hepta-1,6-diene-3,5-dione structural scaffold, their biological activity, and uses thereofPublication Number: US-2013338160-A1Priority Date: 2007-01-08
- Compounds with (1E, 6E)-1,7-bis-(3,4-dimethoxyphenyl)-4,4-disubstituted-hepta-1,6-diene-3,5-dione structural scaffold, their biological activity, and uses thereofPublication Number: US-2015190351-A1Priority Date: 2007-01-08
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Discovery Solutions, Supporting the chemistry needs of clients in the Medical, Analytical and Bio Sciences
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SEE MORE………Integrated Solutions, Manufacturing Solutions, Products,
Can’t Find? Let’s Connect
Phone : +91 897704 2010 / +91 9177075735, Email : info@anaxlab.com
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join me on Linkedin
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| Clinical data | |
|---|---|
| Other names | ASC-JM-17; ASC-JM17; JM17; ALZ-003; ALZ003 |
| Identifiers | |
| IUPAC name | |
| CAS Number | 1039760-91-2 |
| PubChem CID | 25183127 |
| DrugBank | DB16931 |
| ChemSpider | 64854816 |
| UNII | 5VLL140BN9 |
| ChEMBL | ChEMBL5266600 |
| Chemical and physical data | |
| Formula | C28H32O6 |
| Molar mass | 464.558 g·mol−1 |
| 3D model (JSmol) | Interactive image |
| SMILES | |
| InChI | |
References
- “Proposed INN: List 131 International Nonproprietary Names for Pharmaceutical Substances (INN)” (PDF). WHO Drug Information. 38 (2): 428. 2024.
- Chang KH, Chen CM (May 2024). “The Role of NRF2 in Trinucleotide Repeat Expansion Disorders”. Antioxidants. 13 (6): 649. doi:10.3390/antiox13060649. PMC 11200942. PMID 38929088.
- Yuan J, Zhang S, Zhang Y (December 2018). “Nrf1 is paved as a new strategic avenue to prevent and treat cancer, neurodegenerative and other diseases”. Toxicology and Applied Pharmacology. 360: 273–283. Bibcode:2018ToxAP.360..273Y. doi:10.1016/j.taap.2018.09.037. PMID 30267745.
- Bott LC, Badders NM, Chen KL, Harmison GG, Bautista E, Shih CC, et al. (May 2016). “A small-molecule Nrf1 and Nrf2 activator mitigates polyglutamine toxicity in spinal and bulbar muscular atrophy”. Human Molecular Genetics. 25 (10): 1979–1989. doi:10.1093/hmg/ddw073. PMC 5062587. PMID 26962150.
- Wu YL, Chang JC, Chao YC, Chan H, Hsieh M, Liu CS (July 2022). “In Vitro Efficacy and Molecular Mechanism of Curcumin Analog in Pathological Regulation of Spinocerebellar Ataxia Type 3”. Antioxidants. 11 (7): 1389. doi:10.3390/antiox11071389. PMC 9311745. PMID 35883884.
- Sangotra A, Lieberman AP (February 2025). “Therapeutic targeting of the polyglutamine androgen receptor in Spinal and Bulbar Muscular Atrophy”. Expert Opinion on Therapeutic Targets: 1–13. doi:10.1080/14728222.2025.2464173. PMID 39915972.
/////////rosolutamide, antiandrogen, ASC-JM-17, ASC-JM17, JM17, ALZ-003, ALZ003, 5VLL140BN9, ANAX
DR ANTHONY MELVIN CRASTO
ORGANIC SPECTROSCOPY
New Drug Approvals 
