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Engasertib
Engasertib
CAS 1313439-71-2
MF C25H25N3O3 MW415.5 g/mol
6-[4-(1-amino-3-hydroxycyclobutyl)phenyl]-1-ethyl-7-phenylpyrido[2,3-b][1,4]oxazin-2-one
6-{4-[(1S,3S)-1-amino-3-hydroxycyclobutyl]phenyl}-1-ethyl-7-phenyl-1H-pyrido[2,3-b][1,4]oxazin-2(3H)-one
serine/threonine kinase inhibitor, ALM-301, VAD-044, ALM 301, VAD 044, Orphan Drug, K2US8HW4TQ
Engasertib is an oral, once-daily AKT inhibitor developed by Vaderis Therapeutics, primarily investigated as a targeted therapy for Hereditary Hemorrhagic Telangiectasia (HHT). Clinical trials show it safely reduces the frequency and duration of bleeding episodes without an FDA-approved equivalent currently available
Core Information
- Mechanism of Action: Engasertib is a highly selective inhibitor of AKT1 and AKT2. In HHT, mutations in the ALK1 pathway lead to abnormal blood vessel growth driven by an excess of the AKT protein. By inhibiting AKT, the drug promotes vascular stability and reduces vessel fragility.
- Target Indication: Hereditary Hemorrhagic Telangiectasia (HHT) — a rare, severe genetic disorder causing vascular abnormalities and frequent, heavy bleeding, particularly nosebleeds (epistaxis)
Clinical Efficacy & Safety
- Proof-of-Concept Trial: A 12-week, placebo-controlled study with 75 HHT patients evaluated daily doses of 30 mg and 40 mg.
- The 40 mg cohort demonstrated a 41% reduction in mean bleeding duration and a 28% reduction in bleeding frequency, compared to 24% and 18% in the placebo group.
- 61% of patients in the 40 mg group rated their clinical condition as “Much Better”.
- Extended Efficacy: In long-term open-label extensions, benefits were sustained and amplified over 12 months, resulting in a 66% reduction in mean bleeding duration and a 55% reduction in bleeding frequency.
- Side Effects: Generally well-tolerated. The most common side effects (reversible and manageable with supportive care) were mild-to-moderate rash and hyperglycemia
- OriginatorAlmac Discovery
- DeveloperVaderis Therapeutics
- ClassAntineoplastics; Small molecules; Vascular disorder therapies
- Mechanism of ActionProto-oncogene protein c-akt inhibitors
- Orphan Drug StatusYes – Hereditary haemorrhagic telangiectasia
- Phase IVascular disorders
- PreclinicalBreast cancer; Prostate cancer
- No development reportedHereditary haemorrhagic telangiectasia
- 28 Dec 2025No recent reports of development identified for phase-I development in Hereditary haemorrhagic telangiectasia in Belgium (PO, Capsule)
- 28 Dec 2025No recent reports of development identified for phase-I development in Hereditary haemorrhagic telangiectasia in France (PO, Capsule)
- 28 Dec 2025No recent reports of development identified for phase-I development in Hereditary haemorrhagic telangiectasia in Italy (PO, Capsule)
SYN
Example 139: 6-(4-((1s.3s)-1-amino-3-hydroxycyclobutyl)phenyl)-1-ethyl-7-phenyl-1H-pyrido[2,3-b][1,4]oxazin-2(3H)-one
Step 1: tert-butyl ((1s.3s)-1-(4-(1-ethyl-2-oxo-7-phenyl-2.3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl)phenyl)-3-hydroxycyclobutyl)carbamate
In a 15 mL reaction tube was added 6-bromo-1-ethyl-7-phenyl-1H-pyrido[2,3-b][1,4]oxazin-2(3H)-one (50 mg, 0.150 mmol), tert-butyl ((1s,3s)-3-hydroxy-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)cyclobutyl)carbamate (49 mg, 0.125 mmol) and cesium carbonate (204 mg, 0.625 mmol) in a mixture of 1,4-dioxane (2.3 ml) and water (0.8 ml) to give a colourless solution. This was degassed by bubbling nitrogen for 15 minutes, followed by the addition of [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane adduct (20 mg, 0.025 mmol) and degassing for a further 5 minutes. The reaction mixture was heated to 50°C under a nitrogen atmosphere for one hour then allowed to cool to room temperature, diluted with water (5 ml) and extracted into ethyl acetate (3 x 5 ml). The combined organic phases were dried over Na2SO4, filtered and concentrated to dryness under reduced pressure. The residue was purified by Biotage chromatography (cyclohexane:ethyl acetate, gradient elution from 90:10 to 0:100) to give the desired product as an off-white solid (45 mg, 70% yleld). Ή-NMR (500 MHz, CDCl3) δ 7.29-7.35 (5H, m), 7.28 (1H, s), 7.18-7.24 (4H, m), 4.96 (1H, br s), 4.88 (2H, s), 4.05 (1H, br s), 4.01 (2H, q), 2.98 (2H, br s), 2.75 (2H, br s), 1.20-1.51 (9H, br m), 1.32 (3H, t). LCMS (Method D) RT = 1.25 min, M+H+ = 516.20.
Step 2: 6-(4-((1s,3s)-1-amino-3-hydroxycyclobutyl)phenyl)-1-ethyl-7-phenyl-1H-pyrido[2,3-b][1,4]oxazin-2(3H)-one
tert-butyl ((1s,3s)-1-(4-(1-ethyl-2-oxo-7-phenyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl)phenyl)-3-hydroxycyclobutyl)carbamate (45 mg, 0.087 mmol) was dissolved in TFA (1 mL) and stirred for 30 seconds. The solution was immediately concentrated to dryness under reduced pressure. The residue was dissolved in diethyl ether (~3 mL) and concentrated to dryness under reduced pressure three times. The residue was then slurried in diethyl ether (3 mL) and after settling the supernatant solvent removed by pipette. This was repeated three times. The remaining solvent was removed by freeze drylng overnight to give the desired compound as an off-white solid (33 mg, 71% yleld).
1H-NMR (500 MHz, MeOD) δ 7.55 (1H, s), 7.39-7.42 (4H, m), 7.27-7.31 (3H, m), 7.20-7.24 (2H, m), 4.93 (2H, s), 4.01-4.11 (3H, m), 3.03-3.11 (2H, m), 2.42-2.50 (2H, m), 1.28 (3H, t). LCMS (Method D) RT = 0.74 min, M+H+ = 416.20.
SYN
EXAMPLES
Example 1: Synthesis of 6-(4-(l-amino-3-hvdroxycvclobutyl)phenyl)-l-ethyl-7-phenyl-lH-pyrido[2,3-b][l,4]oxazin-2(3H)-one
6-(4-(l-amino-3-hydroxycyclobutyl)phenyl)-l-ethyl-7-phenyl-lH-pyrido[2,3-b][l,4]oxazin-2(3H)-one (referred to herein as “VAD044 free base”) was synthesized in accordance with the protocol as set out in W02011077098 – see in particular Examples 97, 113 and 139 (reproduced below):
Synthesis of 6-(4-((ls,3s)-l-amino-3-hvdroxycvclobutyl)phenyl)-l-ethyl-7-phenyl-lH-pyrido[2,3-bHl,41oxazin-2(3H)-one: from WO2Q11077098 Example 139:
Step 1: tert-butyl((ls,3s)-l-(4-(l-ethyl-2-oxo-7-phenyl-2,3-dihydro-lH-pyrido[2,3-b][l,4]oxazin-6-yl)phenyl)-3-hvdroxycvclobutyl)carbamate
In a 15 mL reaction tube was added 6-bromo-l-ethyl-7-phenyl-lH-pyrido[2,3-b][l,4]oxazin-2(3H)-one* (50 mg, 0.150 mmol), tert-butyl((ls,3s)-3-hydroxy-l-(4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)phenyl)cyclobutyl)carbamate** (49 mg, 0.125 mmol) and cesium carbonate (204 mg, 0.625 mmol) in a mixture of 1,4-dioxane (2.3 ml) and water (0.8 ml) to give a colourless solution. This was degassed by bubbling nitrogen for 15 minutes, followed by the addition of [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(ll) dichloromethane adduct (20 mg, 0.025 mmol) and degassing for a further 5 minutes. The reaction mixture was heated to 50°C under a nitrogen atmosphere for one hour then allowed to cool to room temperature, diluted with water (5 ml) and extracted into ethyl acetate (3 x 5 ml). The combined organic phases were dried over Na2SO4, filtered and concentrated to dryness under reduced pressure. The residue was purified by Biotage chromatography (cyclohexane:ethyl acetate, gradient elution from 90:10 to 0:100) to give the desired product as an off- white solid (45 mg, 70% yield). 1H-NMR (500 MHz, CDCI3) 6 7.29-7.35 (5H, m), 7.28 (1H, s), 7.18-7.24 (4H, m), 4.96 (1H, br s), 4.88 (2H, s), 4.05 (1H, br s), 4.01 (2H, q), 2.98 (2H, br s), 2.75 (2H, br s), 1.20-1.51 (9H, br m), 1.32 (3H, t). LCMS (Method D) RT = 1.25 min, M+H+ = 516.20.
tert-butyl((ls,3s)-l-(4-(l-ethyl-2-oxo-7-phenyl-2,3-dihydro-lH-pyrido[2,3-b][l,4]oxazin-6-yl)phenyl)-3- hydroxycyclobutyl)carbamate (45 mg, 0.087 mmol) was dissolved in TFA (1 mL) and stirred for 30 seconds. The solution was immediately concentrated to dryness under reduced pressure. The residue was dissolved in diethyl ether (~3 mL) and concentrated to dryness under reduced pressure three times. The residue was then slurried in diethyl ether (3 mL) and after settling the supernatant solvent removed by pipette. This was repeated three times. The remaining solvent was removed by freeze drying overnight to give the desired compound as an off-white solid (33 mg, 71% yield). 1H-NMR (500 MHz, MeOD) 6 7.55 (1H, s), 7.39- 7.42 (4H, m), 7.27-7.31 (3H, m), 7.20- 7.24 (2H, m), 4.93 (2H, s), 4.01-4.11 (3H, m), 3.03-3.1 1 (2H, m), 2.42-2.50 (2H, m), 1.28 (3H, t). LCMS (Method D) RT = 0.74 min, M+H+ = 416.20.
To a suspension of sodium hydride (5.31 g, 133 mmol) in 1,4-dioxane (250 ml), ethyl glycolate (12.56 ml,
133 mmol) was added drop wise over a period of 30 minutes ensuring that the temperature was maintained below 30°C. The resulting thick suspension was stirred at room temperature for 15 minutes.
In a separate II round- bottomed flask was added 5-bromo-2-chloro-3-nitropyridine (21 g, 88 mmol) in
1,4-dioxane (150 ml) to give a brown solution. The suspension of sodium hydride and ethyl glycolate was added drop wise over a period of 30 minutes at 0°C. The resulting reaction mixture was heated to 80°C overnight.
The reaction mixture was concentrated under reduced pressure and the crude residue was purified by
Biotage silica chromatography (gradient 0% to 10% ethyl acetate in n-hexanes) to give the title compound
(1 ,8g, 44%).1H NMR (500 MHz, CDCI3) 6 8.48 (1H, s), 8.42 (1H, s), 5.07 (2H, s), 4.28-4.24 (2H, q), 1.31-1.28
(3H, t).
In a II round-bottomed flask was added ethyl 2-(5-bromo-3-nitropyridin-2-yloxy)acetate (18.33 g, 60.1 mmol), phenylboronic acid (10.99 g, 90 mmol), triphenylphosphine (4.73 g, 18.02 mmol) and cesium fluoride (45.6 g, 300 mmol) in 1,2-dimethoxyethane (300 ml) to give a yellow solution. The reaction mixture was degassed by bubbling nitrogen for 30 minutes. Pallad ium (II ) acetate (2.023 g, 9.01 mmol) was added and the mixture was heated to 75°C under a nitrogen atmosphere overnight. The reaction mixture was allowed to cool to room temperature and concentrated to dryness under reduced pressure to give a brown solid. This was re-dissolved in dichloromethane, filtered and concentrated to dryness under reduced pressure to give a brown solid The crude residue was purified via Biotage chromatography (gradient 5% to 60% ethyl acetate in n-hexanes) to give the title compound (6.9g, 38%). 1H NMR (500 MHz, CDCI3) 6 8.58 (1H, s), 8.56 (1H, s), 7.59-7.52 (2H, m), 7.48-7.46 (2H, m), 7.45-7.43 (1H, m), 5.13 (2H, s), 4.30-4.26 (2H, q), 1.33-1.30 (3H, t).
In a 500 ml round-bottomed flask was added ethyl 2-(3-nitro-5-phenylpyridin-2-yloxy)acetate (4.6 g, 15.22 mmol) in hydrochloric acid, 37% (40 ml) to give a yellow suspension. The mixture was cooled to 0-5°C followed by the portion wise addition of tin powder (9.94 g, 84 mmol). The addition proved to be exothermic. Caution should be taken while adding. The mixture was then stirred at room temperature for further 30 minutes until all foaming ceased. The reaction mixture was heated to 80°C under a nitrogen atmosphere for 3 hours. The reaction mixture cooled to room temperature and diluted with water (800ml). The white precipitate was isolated by filtration, washed with water (100 ml) and sucked dry to give a white solid. The solid was azeotroped with toluene (3 x 30 ml) to give a white solid as the title compound (2.6g, 77%). XH NMR (500 MHz, (CD3)2SO) 6 10.41 (1H, s), 8.10 (1H, s), 7.59 (2H, d), 7.49-7.42 (2H, t), 7.39-7-38 (1H, d), 4.83 (2H, s).
Step 4: 6-bromo-7-phenyl-lH-pyrido[2,3-b][l,4]oxazin-2(3H)-one
In a 10ml microwave vial was 7-phenyl-l H-pyrido[2,3-b][l ,4]oxazin-2(3H)-one (50 mg, 0.221 mmol) and N-bromosuccinimide (78.6 mg, 0.441 mmol) in dimethylformamide (1 ml). The reaction mixture was heated to 80°C under microwave irradiation for 30 minutes. The reaction mixture was cooled to room
temperature and diluted with ethyl acetate (10ml). The organic solution was washed with water (2x10ml) and brine (2x10ml). The organic phase was dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The crude residue was purified via Biotage chromatography (gradient 0% to 5% methanol in dichloromethane) to give the title compound as a yellow solid (61 mg, 90%). 1H NMR (500 MHz, CD3OD) 6 7.48-7.32 (5H, m), 7.12 (1 H, s), 4.82 (2H, s).
In a 15 mL reaction tube was added 6-bromo-7-phenyl-lH-pyrido[2,3-b][l,4]oxazin-2(3H)-one (300 mg, 0.983 mmol), iodoethane (0.095 mL, 1.180 mmol) and potassium carbonate (408 mg, 2.95 mmol) in anhydrous N,N-dimethylformamide (1 mL) to give a brown suspension. This was stirred at 50 °C under a nitrogen atmosphere for 60 minutes. The reaction mixture was diluted with saturated sodium bicarbonate solution (5 mL) and extracted into ethyl acetate (3 x 5 mL). The combined organic phases were washed with 50:50 water.brine (3 x 5 mL), dried over Na2SO4, filtered and concentrated to dryness under reduced pressure to give a brown solid. This was purified by Biotage chromatography (25g silica cartridge, cyclohexane:ethyl acetate, gradient elution from 90:10 to 20:80) to give the title compound as a beige solid (160 mg, 48.8 % yield). XH NMR (500 MHz, CDCI3) 6 7.58-7.37 (5H, m), 7.21 (1H, s), 4.86 (2H, s), 3.96 (2H, q), 1.27 (3H, t). LCMS (Method D) RT 1.293 min, M+l= 334.
n a 40 mL reaction tube was added tert-butyl(ls,3s)-l-(4-bromophenyl)-3- hydroxycyclobutylcarbamate*** (0.25 g, 0.731 mmol) in anhydrous tetrahydrofuran (14 ml) to give a colourless solution. This was degassed by bubbling nitrogen for 20 minutes, followed by the addition of [l,l’-bis(diphenylphosphino)ferrocene]dichloropalladium(ll) dichloromethane adduct (60 mg, 0.073 mmol). After bubbling nitrogen for a further 15 minutes, potassium acetate (143 mg, 1.461 mmol) and bis(pinacolato)diboron (223 mg, 0.877 mmol) were added. The reaction mixture was heated to reflux overnight then concentrated to dryness under reduced pressure and purified by Biotage chromatography (cyclohexane:ethyl acetate, gradient elution from 88:12 to 0:100) to give the desired product as a colourless oil that solidified upon standing (240 mg, 84% yield). 1H-NMR (500 MHz, CDCI3) 6 7.71 (2H, d), 7.44 (2H, d), 4.15 (1H, br s), 2.87-2.98 (2H, m), 2.27-2.44 (2H, m), 1.22-1.49 (21H, br m).
(*** synthesis described in WO2009148887 and WO2009148916)
ADVT
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References
- Inhibitors of akt activityPublication Number: EP-2516435-B1Priority Date: 2009-12-23Grant Date: 2014-08-06
- Inhibitors of akt activityPublication Number: WO-2011077098-A1Priority Date: 2009-12-23
- Inhibitors of akt activityPublication Number: EP-2516435-B8Priority Date: 2009-12-23Grant Date: 2014-10-15
- Inhibitors of akt activityPublication Number: EP-2516435-A1Priority Date: 2009-12-23
- Inhibitors of AKT activityPublication Number: US-9221838-B2Priority Date: 2009-12-23Grant Date: 2015-12-29
- Allosteric akt inhibitors for use in the treatment of hereditary hemorrhagic telangiectasiaPublication Number: US-2024092801-A1Priority Date: 2020-09-30
- Allosteric akt inhibitors for use in the treatment of hereditary hemorrhagic telangiectasiaPublication Number: WO-2022069552-A1Priority Date: 2020-09-30
- Allosteric akt inhibitors for use in the treatment of hereditary hemorrhagic telangiectasiaPublication Number: EP-4221713-A1Priority Date: 2020-09-30
- Inhibitors of akt activityPublication Number: US-2013116243-A1Priority Date: 2009-12-23
- Inhibitors of akt activityPublication Number: WO-2011077098-A9Priority Date: 2009-12-23
////////engasertib, anax labs, serine/threonine kinase inhibitor, ALM-301, VAD-044, ALM 301, VAD 044, Orphan Drug, K2US8HW4TQ
Encofosbuvir
Encofosbuvir, Yiqibuvir
CAS 2232134-77-7
MF C30H42FN4O13PS MW 748.7 g/mol
- L-Alanine, O3-[N-(methoxycarbonyl)-L-methionyl]-[P(S),2’R]-2′-deoxy-2′-fluoro-3-(hydroxymethyl)-2′-methyl-P-phenyl-5′-uridylyl-, 1-methylethyl ester
- O3-[N-(Methoxycarbonyl)-L-methionyl]-[P(S),2’R]-2′-deoxy-2′-fluoro-3-(hydroxymethyl)-2′-methyl-P-phenyl-5′-uridylyl-L-alanine 1-methylethyl ester
[3-[(2R,3R,4R,5R)-3-fluoro-4-hydroxy-3-methyl-5-[[[[(2S)-1-oxo-1-propan-2-yloxypropan-2-yl]amino]-phenoxyphosphoryl]oxymethyl]oxolan-2-yl]-2,6-dioxopyrimidin-1-yl]methyl (2S)-2-(methoxycarbonylamino)-4-methylsulfanylbutanoate
antiviral, HEC 110114; Yiqibuvir, CHINA 2025, APPROVALS 2025, 82E4Q8WQV7
Encofosbuvir is a novel, oral small-molecule direct-acting antiviral (DAA) drug used to treat the hepatitis C virus (HCV). Approved by China’s National Medical Products Administration (NMPA) in March 2025, it serves as a core component of a domestic, pan-genotypic treatment regimen.
🔬 Mechanism of Action
Encofosbuvir works by targeting the machinery the virus needs to replicate itself:
- Target Enzyme: It functions as an HCV NS5B RNA-dependent RNA polymerase inhibitor.
- Viral Suppression: By selectively binding to this polymerase, it blocks the synthesis of viral RNA, effectively halting the replication and spread of the hepatitis C virus in mammals
Clinical Indications and Usage
According to the official regulatory updates from the China NMPA, encofosbuvir is prescribed under specific clinical parameters:
- Combination Therapy: It must be used in combination with netanasvir (specifically netanasvir phosphate capsules).
- Target Genotypes: The regimen is highly effective across multiple viral strains, covering HCV genotypes 1, 2, 3, and 6.
- Patient Profile: It is indicated for adult patients who are treatment-naïve (never treated before) or who have been previously treated with interferon. It is safe for use in patients with or without compensated liver cirrhosis.
The drug is classified as a Class 1 innovative drug, representing a milestone in self-developed, domestic intellectual property:
- Developers: It was jointly developed and brought to market by Sunshine Lake Pharma (a subsidiary of HEC Pharm) and YiChang HEC ChangJiang Pharmaceutical Co., Ltd.
- Dosage Form: It is distributed commercially as 0.3g tablets.
- Therapeutic Context: This medication expands the developer’s innovative hepatitis C pipeline, building upon their previously approved portfolio like emitasvir phosphate
- OriginatorHEC Pharm; Sunshine Lake Pharma
- DeveloperSunshine Lake Pharma
- ClassAntivirals
- Mechanism of ActionHepatitis C virus NS 5 protein inhibitors
- RegisteredHepatitis C
- 27 Mar 2025Registered for Hepatitis C (Combination therapy, Treatment-naive) in China (PO)
- 08 Feb 2025Preregistered for Hepatitis C (Combination therapy, Treatment-experienced) in China (PO)
- 08 Feb 2025Registered for Hepatitis C (Combination therapy, Treatment-experienced) in China (PO)
Encofosbuvir is an antiviral drug used to treat hepatitis C virus (HCV). In China, encofosbuvir is approved for use in combination with netanasvir 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.[1]
SYN
[0515](S)-(3-((2R,3R,4R,5R)-3-fluoro-4-hydroxy-5-((((S)-(((S)-1-isopropoxy-1-oxopropyl-2-yl)amino)(phenoxy)phosphoryl)oxy)methyl)-3-methyltetrahydrofuran-2-yl)-2,6-dioxo-2,3-dihydropyrimidin-1(6H)-yl)methyl-2-((methoxycarbonyl)amino)-4-(methylthio)butyrate
[0531]4) Synthesis of compound 3
Compound 3-6 (3.63 g, 4.2 mmol, 1 eq) was dissolved in acetone (12 mL), and water (9 mL), trifluoroacetic acid (3 mL), and glacial acetic acid (12 mL) were added sequentially at room temperature, followed by a reaction time of 2 hours. After the reaction was monitored by TLC until complete, 30 mL of dichloromethane was added to the reaction solution, stirred thoroughly, and allowed to stand for phase separation. The organic phase was washed sequentially with water (10 mL × 3), saturated sodium chloride (10 mL), dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The solution was purified by column chromatography using DCM:MeOH = 50:1 as the eluent, yielding 2.8 g of a white foamy solid.
[0534]MS-ESI: m/z 748.8[M+1] +；
[0535]
1H NMR(400MHz,CDCl 3)δ7.49(d,J＝8.2Hz,1H),7.34(d,J＝7.6Hz,2H),7.24–7.16(m,3H),6.19(d,J＝17.3Hz,1H),6.07–5.94(m,2H),5.75(d,J＝8.3Hz,1H),5.41(d,J＝7.4Hz,1H),5.07–4.95(m,1H),4.58–4.39(m,3H),4.12(d,J＝8.6Hz,1H),4.02–3.80(m,4H),3.67(s,3H),2.52(t,J＝7.5Hz,2H),2.14–1.90(m,5H),1.37(dd,J＝18.4,14.3Hz,6H),1.24(d,J＝6.3Hz,6H)。
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References
“Netanasvir Phosphate Capsules Approved for Marketing by China NMPA”. National Medical Products Administration. 2025-06-11.
| Clinical data | |
|---|---|
| Trade names | 英强布韦 |
| Legal status | |
| Legal status | Rx in China |
| Identifiers | |
| IUPAC name | |
| CAS Number | 2232134-77-7 |
| PubChem CID | 141522644 |
| UNII | 82E4Q8WQV7 |
| Chemical and physical data | |
| Formula | C30H42FN4O13PS |
| Molar mass | 748.71 g·mol−1 |
| 3D model (JSmol) | Interactive image |
| SMILES | |
| InChI | |
//////////encofosbuvir, anax labs, antiviral, HEC 110114; Yiqibuvir, CHINA 2025, APPROVALS 2025, 82E4Q8WQV7
Emupertinib
Emupertinib
CAS 2472802-77-8
MFC30H26N8O MW514.6 g/mol
2-Pyrazinecarboxamide, N-[4-[4-amino-6-ethynyl-5-(3-quinolinyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]bicyclo[2.2.1]hept-1-yl]-5-methyl-
N-{4-[4-amino-6-ethynyl-5-(quinolin-3-yl)-7Hpyrrolo[2,3-d]pyrimidin-7-yl]bicyclo[2.2.1]heptan-1-yl}-
5-methylpyrazine-2-carboxamide
epidermal growth factor receptor tyrosine kinase, inhibitor, antineoplastic, TAS3351, TAS 3351, CU9YW8A5TP
Emupertinib is a potent, small-molecule epidermal growth factor receptor (EGFR) tyrosine kinase inhibitor. It possesses selective antineoplastic potential for targeting specific mutant profiles of cancer cells. The compound was originally developed by Taiho Pharmaceutical Co., Ltd. under the developmental code TAS3351
Development Profile
The International Nonproprietary Name (INN) for this therapeutic chemical structure was formally proposed under the World Health Organisation (WHO) proposed INN list 132 in early 2025. Global research pipelines list the compound’s structural classification profile within non-small cell lung cancer (NSCLC) primary discovery programs. The drug currently remains a specialized compound designated for global laboratory research use only, rather than standard human prescription or veterinary clinical treatments
SYN
[0184][Example 37]
N-(4-(4-amino-6-ethynyl-5-(quinoline-3-yl)-7H-pyrrolo[2,3-d]pyrimidine-7-yl)bicyclo[2.2.1]heptan-1-yl)
-5-methylpyrazine-2-carboxamide The title compound was obtained by following the same method as in Example 29 (step 6), except that 5-methylpyrazine-2-carboxylic acid was used instead of 5-(fluoromethyl)-2-methylpyrazole-3-carboxylic acid used in Example 29.
(Step 4)
Synthesis of N-(4-(4-amino-6-ethynyl-5-(quinoline-3-yl)-7H-pyrrolo[2,3-d]pyrimidine-7-yl)bicyclo[2.2.1]heptan-1-yl)-5-methylpyrazine-2-carboxamide (compound (1))
[Chemical Formula 7]
It can be obtained by deprotecting the acetylene protecting group TES of N-(4-(4-amino-5-(quinoline-3-yl)-6-((triethylsilyl)ethynyl)-7H-pyrrolo[2,3-d]pyrimidine-7-yl)bicyclo[2.2.1]heptan-1-yl)-5-methylpyrazine-2-carboxamide obtained in Step 3 under basic conditions.
The reagents used to create basic conditions are not particularly limited as long as the reaction proceeds, but examples of inorganic bases include metal hydroxides (sodium hydroxide, calcium hydroxide, etc.), metal hydrides (lithium hydride, sodium hydride, etc.), and metal carbonates (sodium carbonate, potassium carbonate, cesium carbonate, calcium carbonate, lithium carbonate, magnesium carbonate, sodium bicarbonate, etc.). Examples of organic bases include metal alkoxides (sodium methoxide, potassium tert-butoxide, etc.), metal amides (sodium amide, lithium diisopropylamide, etc.), alkyl metal compounds (n-butyllithium, trimethylaluminum, etc.), alkylamines (triethylamine, tetramethylethylenediamine, piperidine, 1,4-diazabicyclo[2.2.2]octane, etc.), heterocyclic amines (diazabicycloundecene, pyridine, imidazole, etc.), and quaternary ammonium fluorides (tetra-n-butylammonium fluoride). Preferably, the reagent used to create basic conditions is a reagent that does not contain fluoride ions, more preferably a metal carbonate, and even more preferably potassium carbonate. These can be used alone or in combination to adjust the pH to the desired level.
The amount of reagent used is not particularly limited as long as the reaction proceeds, but for example, 0.1 to 50 moles can be used per mole of the starting compound (the compound represented by formula (II)). Preferably, 0.1 to 10 moles, and more preferably 0.1 to 2 moles.
ADVT
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References
Substituted pyrrolo[2,3-d]pyrimidines as EGFR inhibitors
Publication Number: US-11786534-B2
Priority Date: 2019-02-15
Grant Date: 2023-10-17
- Crystal of 7h-pyrrolo[2,3-d]pyrimidine-4-amine derivativePublication Number: EP-4512808-A1Priority Date: 2022-04-22
- 7H-pyrrolo[2,3-d]pyrimidin-4-amine derivativePublication Number: KR-102645237-B1Priority Date: 2019-02-15Grant Date: 2024-03-07
- 7h-pyrrolo[2,3-d]pyrimidine-4-amine derivativePublication Number: WO-2020166680-A1Priority Date: 2019-02-15
- 7h-pyrrolo[2,3-d]pyrimidine-4-amine derivativePublication Number: US-2022160719-A1Priority Date: 2019-02-15
- 7H-Pyrrolo[2,3-d]pyrimidin-4-amine derivativesPublication Number: CN-113453764-BPriority Date: 2019-02-15Grant Date: 2024-04-16
- Brain-migrating tumor treatment agent containing, as active ingredient, n-(4-(4-amino-6-ethynyl-5-(quinolin-3-yl)-7h-pyrrolo[2,3-d]pyrimidin-7-yl) bicyclo[2.2.1]heptan-1-yl)-5-methylpyrazine-2-carboxamide or salt thereofPublication Number: WO-2025127108-A1Priority Date: 2023-12-13
- Crystals of 7h-pyrrolo[2,3-d]pyrimidin-4-amine derivativesPublication Number: WO-2025072720-A1Priority Date: 2023-09-29
- Crystal of 7h-pyrrolo[2,3-d]pyrimidine-4-amine derivativePublication Number: WO-2023204303-A1Priority Date: 2022-04-22
- Method for producing 7h-pyrrolo[2,3-d]pyrimidine-4-amine derivativePublication Number: WO-2023204304-A1Priority Date: 2022-04-22
- Method for producing 7h-pyrrolo[2,3-d]pyrimidine-4-amine derivativePublication Number: US-2025270214-A1Priority Date: 2022-04-22
///////emupertinib, anax labs, epidermal growth factor receptor tyrosine kinase, inhibitor, antineoplastic, TAS3351, TAS 3351, CU9YW8A5TP
Sonrotoclax
Sonrotoclax
CAS 2383086-06-2
MW 890.1 g/mol, MFC49H59N7O7S
FDA APPROVED 5/13/2026, Beqalzi, APPROVALS 2026, BGB-11417, BGB 11417, 30R67U9KYS
N-[4-[(4-hydroxy-4-methylcyclohexyl)methylamino]-3-nitrophenyl]sulfonyl-4-[2-[(2S)-2-(2-propan-2-ylphenyl)pyrrolidin-1-yl]-7-azaspiro[3.5]nonan-7-yl]-2-(1H-pyrrolo[2,3-b]pyridin-5-yloxy)benzamide
- 2-((1H-Pyrrolo[2,3-b]pyridin-5-yl)oxy)-N-((4-((((1r,4r)-4-hydroxy-4-methylcyclohexyl)methyl)amino)-3-nitrophenyl)sulfonyl)-4-(2-((S)-2-(2-isopropylphenyl)pyrrolidin-1-yl)-7-azaspiro[3.5]nonan-7-yl)benzamide
- 2-((1H-Pyrrolo[2,3-b]pyridin-5-yl)oxy)-N-((4-(((trans-4-hydroxy-4-methylcyclohexyl)methyl)amino)-3-nitrophenyl)sulfonyl)-4-(2-((S)-2-(2-isopropylphenyl)pyrrolidin-1-yl)-7-azaspiro[3.5]nonan-7-yl)benzamide
To treat adults with relapsed or refractory mantle cell lymphoma after at least two lines of systemic therapy, including a Bruton’s tyrosine kinase inhibitor
Sonrotoclax is a potent, orally active Bcl2 inhibitor. Sonrotoclax has effective cell killing effect against a variety of lymphoma and leukemia cell lines.
Regulatory Status & Primary Indication
On May 13, 2026, the U.S. Food and Drug Administration (FDA) granted accelerated approval to sonrotoclax for treating adult patients with relapsed or refractory mantle cell lymphoma (MCL). [1]
- Eligibility Requirement: Patients must have undergone at least two prior lines of systemic therapy, which must include a Bruton’s tyrosine kinase (BTK) inhibitor.
- Clinical Performance: In the supporting Phase 1/2 BGB-11417-201 trial, sonrotoclax demonstrated an overall response rate (ORR) of 52% and a median time to response of 1.9 months
Sonrotoclax is an orally bioavailable inhibitor of the anti-apoptotic protein B-cell lymphoma 2 (Bcl-2), with potential pro-apoptotic and antineoplastic activities. Upon oral administration, sonrotoclax specifically binds to and inhibits the activity of the pro-survival protein Bcl-2. This restores apoptotic processes and inhibits cell proliferation in Bcl-2-overexpressing tumor cells. Bcl-2, a protein that belongs to the Bcl-2 family, is overexpressed in various tumor cell types and plays an important role in the negative regulation of apoptosis. Its tumor expression is associated with increased drug resistance and cancer cell survival.
Sonrotoclax is an investigational new drug that is being evaluated for the treatment of hematologic malignancies, particularly chronic lymphocytic leukemia (CLL) and small lymphocytic lymphoma (SLL).[1] It is a potent and selective BCL2 inhibitor that can overcome resistance associated with BCL2 mutations, such as the G101V variant, which limits the effectiveness of first-generation inhibitors like venetoclax.[2]
SYN
2-((1H-pyrrolo[2,3-b]pyridin-5-yl)oxy)-N-((4-((((1r,4r)-4-hydroxy-4-methylcyclohexyl)methyl)amino)-3-nitrophenyl)sulfonyl)-4-(2-((S)-2-(2-isopropylphenyl)pyrrolidin-1-yl)-7-azaspiro[3.5]nonan-7-yl)benzamide (hereinafter sonrotoclax).
SYN
2-((1H-pyrrolo[2,3-b]pyridin-5-yl)oxy)-N-((4-((((1r,4r)-4-hydroxy-4-methylcyclohexyl)methyl)amino)-3-nitrophenyl)sulfonyl)-4-(2-((S)-2-(2-isopropylphenyl)pyrrolidin-1-yl)-7-azaspiro[3.5]nonan-7-yl)benzamide
Step 9: 2-((1H-pyrrolo[2,3-b]pyridin-5-yl)oxy)-N-((4-((((1r,4r)-4-hydroxy-4-methylcyclohexyl)methyl)amino)-3-nitrophenyl)sulfonyl)-4-(2-((S)-2-(2-isopropylphenyl)pyrrolidin-1-yl)-7-azaspiro[3.5]nonan-7-yl)benzamide
SYN
- US11420968
- https://patentscope.wipo.int/search/en/detail.jsf?docId=US335022833&_cid=P10-MP4VD4-31735-1
Example F43: 2-((1H-pyrrolo[2,3-b]pyridin-5-yl)oxy)-N-((4-((((1r,4r)-4-hydroxy-4-methylcyclohexyl)methyl)amino)-3-nitrophenyl)sulfonyl)-4-(2-((S)-2-(2-isopropylphenyl)pyrrolidin-1-yl)-7-azaspiro[3.5]nonan-7-yl)benzamide
PAT
- Ketal Protected Intermediate for Sonrotoclax and Preparation Method ThereofPublication Number: US-2025320207-A1Priority Date: 2022-12-27
- Methods of treating multiple myeloma using bcl-2 inhibitorPublication Number: US-2025161279-A1Priority Date: 2022-07-21
- Methods of treating myeloid malignancies using bcl-2 inhibitorPublication Number: WO-2023218410-A1Priority Date: 2022-05-12
- Methods of treating myeloid malignancies using bcl-2 inhibitorPublication Number: US-2025057821-A1Priority Date: 2022-05-12
- Methods of treating myeloid malignancies using bcl-2 inhibitorPublication Number: EP-4522169-A1Priority Date: 2022-05-12
- Methods of cancer treatment using bcl-2 inhibitorPublication Number: WO-2021110102-A1Priority Date: 2019-12-02
- Bcl-2 inhibitorsPublication Number: US-2022402915-A1Priority Date: 2018-04-29
- Bcl-2 inhibitorsPublication Number: US-11420968-B2Priority Date: 2018-04-29Grant Date: 2022-08-23
- Bcl-2 inhibitorsPublication Number: US-2021269433-A1Priority Date: 2018-04-29
- Bcl-2 InhibitorsPublication Number: US-2024376104-A1Priority Date: 2018-04-29
- Bcl-2 inhibitorsPublication Number: EP-3788042-B1Priority Date: 2018-04-29Grant Date: 2025-02-12
- Bcl-2 inhibitorsPublication Number: EP-4545515-A1Priority Date: 2018-04-29
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References
References
- “Sonrotoclax – BeiGene”. AdisInsight. Springer Nature Switzerland AG.
- Tomkins O, D’Sa S (2024). “Review of BCL2 inhibitors for the treatment of Waldenström’s macroglobulinaemia and non-IgM lymphoplasmacytic lymphoma”. Frontiers in Oncology. 14 1490202. doi:10.3389/fonc.2024.1490202. PMC 11570586. PMID 39558954.
| Clinical data | |
|---|---|
| Pronunciation | /sɒnˈroʊtəklæks/ son-ROH-tə-klaks |
| Identifiers | |
| IUPAC name | |
| CAS Number | 2383086-06-2 |
| PubChem CID | 149553242 |
| ChemSpider | 129309008 |
| UNII | 30R67U9KYS |
| KEGG | D12883 |
| ChEMBL | ChEMBL5314951 |
| Chemical and physical data | |
| Formula | C49H59N7O7S |
| Molar mass | 890.11 g·mol−1 |
| 3D model (JSmol) | Interactive image |
| SMILES | |
| InChI | |
/////////sonrotoclax, anax labs, FDA 2026, APPROVALS 2026, Beqalzi, BGB-11417, BGB 11417, 30R67U9KYS, accelerated approval
Elunetirom
Elunetirom
CAS 2156649-32-8
MF C19H21Cl2NO3 MW382.3 g/mol
2-[3,5-dichloro-4-[(4-hydroxy-3-propan-2-ylphenyl)methyl]phenoxy]-N-methylacetamide
2-(3,5-dichloro-4-{[4-hydroxy-3-(propan-2-yl)phenyl]methyl}phenoxy)-N-methylacetamide
thyroid hormone beta receptor agonist, ABX-002, MA-JD21, ABX 002, MA JD21, QTW4WC4BRX, MA-JD-21,
Elunetirom (ABX-002/MA-JD21) is an oral, brain-penetrant thyroid hormone receptor beta agonist being developed by Autobahn Therapeutics for major depressive disorder (MDD) and bipolar depression. As of early 2026, it is in Phase 2 clinical trials, aiming to treat these disorders with fewer peripheral side effects than traditional treatments.
Key Facts About Elunetirom
- Mechanism: It is a prodrug converted into an active metabolite that selectively targets TR\(\beta \) in the central nervous system (CNS), boosting brain energy and plasticity.
- Development Stage: Currently in Phase 2 trials for major depressive disorder (MDD) and bipolar depression.
- Target Indications: Primarily for psychiatric conditions, with preclinical research for neurodegenerative diseases like multiple sclerosis and adrenomyeloneuropathy.
- Benefits: Designed to offer a favorable safety profile compared to synthetic thyroid hormones, minimizing systemic side effects.
Clinical Status (2025–2026)
As of early 2026, Autobahn Therapeutics has reported positive Phase 1 data, confirming its, safety, tolerability, and ability to engage with brain targets.
- Phase 2 Focus: Evaluating its potential as an add-on (adjunctive) therapy for depression.
- Preclinical Findings: Studies suggest it may help repair myelin (remyelination) and treat cognitive impairment.
Elunetirom, also known by its developmental code names ABX-002 and MA-JD21, is a thyroid hormone receptor agonist which is under development for the treatment of major depressive disorder, bipolar depression, multiple sclerosis, and adrenomyeloneuropathy.[1][2] It is a prodrug of LL-340001 and acts as a potent, selective, and centrally penetrant agonist of the thyroid hormone receptor beta (TRβ).[1][2] The drug produces psychoplastogenic effects similar to those of brain-derived neurotrophic factor (BDNF) in rodents.[2] In addition, it has been found to improve cognitive impairment caused by old age or scopolamine treatment in rodents.[2] Eunetirom is under development by Autobahn Therapeutics.[1] As of December 2025, it is in phase 2 clinical trials for treatment of major depressive disorder and bipolar depression and is in the preclinical research stage of development for multiple sclerosis and adrenomyeloneuropathy.[1]
SYN
PAT
xample 16. Preparation of 2-(3. 5-dichloro-4-(4-hvdroxy-3-isopropylbenzyl) phenoxy)-N-methylacetamide (MA-JD21; 10b)
0142] 2-(3, 5-dichloro-4-(4-hydroxy-3-isopropylbenzyl) phenoxy) acetic acid (100 mg, 0.27 mmol, 1 equiv.) was dissolved in methanol (5 mL) in a sealed tube. Sulfuric acid (1 drop) added to it and the reaction was sealed and heated to 65°C for one hour while stirring. It was cooled to room temperature and TLC analysis (ethyl acetate: hexane 1 : 1) shows complete conversion to the intermediate methyl ester. To this was then added 40% methyl amine in water (320μ1, 4mmol, 15 equiv.). The reaction is resealed and heated to 65°C for one hour. The reaction flask was cooled to room temperature and sodium hydroxide (0.5N, 10 mL) added to it. The reaction product was extracted with dichoromethane (3 x 50 mL). The organic layers were combined, dried on anhydrous Mg2S04, filtered and concentrated. Purification by flash chromatography (50% hexane in ethylacetate) gave the product as a white solid (65 mg, 0.17 mmol, 63%). XH NMR (400 MHz, MeOH-c¾): 5=7.12 (s, 2H), 7.01 (d, IH, J=1.98Hz), 6.77 (dd, IH, J=8.21Hz, 2.26Hz), 6.62 (d, IH, J=8.21Hz), 4.56 (s, 2H), 4.15 (s, 2H), 3.23 (septet, IH, J=7.14Hz), 2.85 (s, 3H), 1.17 (d, 6H, J= 6.93Hz). HRMS exact mass calculated for C19H21CI2NO3 [M + H] +: m/z 384.09455, found m/z 384.09473.
PAT
- Derivatives of sobetiromePublication Number: US-10870616-B2Priority Date: 2016-05-18Grant Date: 2020-12-22
- Process for the preparation of derivatives of sobetiromePublication Number: EP-3936497-A1Priority Date: 2016-05-18
- Subiterol DerivativesPublication Number: CN-113277958-APriority Date: 2016-05-18
- Sobetarom derivativePublication Number: JP-6982004-B2Priority Date: 2016-05-18Grant Date: 2021-12-17
- Derivatives of sobetiromePublication Number: US-2019210950-A1Priority Date: 2016-05-18
- History of SubtirumPublication Number: IL-263050-APriority Date: 2016-05-18
- Derivatives of sorbetyromPublication Number: KR-102331596-B1Priority Date: 2016-05-18Grant Date: 2021-11-25
- Derivatives of sobetiromePublication Number: EP-3457851-B1Priority Date: 2016-05-18Grant Date: 2021-06-23
- Fatty acid amide hydrolase (faah) cleavable prodrugs of thyromimetics and combination with peripherally restricted faah inhibitorsPublication Number: EP-4333844-A1Priority Date: 2021-05-06
- Isotopic thyromimetic compoundsPublication Number: US-2023348364-A1Priority Date: 2020-06-03
- Sobetarom derivativePublication Number: JP-2022033788-APriority Date: 2016-05-18
- Derivatives of sobetiromePublication Number: AU-2017267734-A1Priority Date: 2016-05-18
- Derivatives of sobetiromePublication Number: WO-2017201320-A1Priority Date: 2016-05-18
- Fatty acid amide hydrolase (faah) cleavable prodrugs of thyromimetics and combination with peripherally restricted faah inhibitorsPublication Number: US-2024254075-A1Priority Date: 2021-05-06
- Fatty acid amide hydrolase (FAAH) cleaves prodrugs of thyroxine drugs and combinations with peripherally restricted FAAH inhibitorsPublication Number: CN-117597122-APriority Date: 2021-05-06
- Fatty acid amide hydrolase (faah) cleavable prodrugs of thyromimetics and combination with peripherally restricted faah inhibitorsPublication Number: WO-2022236133-A1Priority Date: 2021-05-06
- Fatty acid amide hydrolase (faah) cleavable prodrugs of thyromimetics and combination with peripherally restricted faah inhibitorsPublication Number: AU-2022271304-A1Priority Date: 2021-05-06
- Fatty acid amide hydrolase (faah) cleavable prodrugs of thyromimetics and combination with peripherally restricted faah inhibitorsPublication Number: CA-3217789-A1Priority Date: 2021-05-06
ADVT
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References
References
- “Autobahn Therapeutics”. AdisInsight. 2 December 2025. Retrieved 7 January 2026.
- Harris J, Baccei J, Franey B, Vivian JA, MacKenna D, Stratton W, et al. (January 2026). “ACNP 64th Annual Meeting: Poster Abstracts P584-P872”. Neuropsychopharmacology. 51 (Suppl 1). Nature Publishing Group: 410–571. doi:10.1038/s41386-025-02281-2. PMID 41507446.
| Clinical data | |
|---|---|
| Other names | ABX-002; ABX002; MA-JD21; MA-JD-21 |
| Routes of administration | Oral[1] |
| Drug class | Thyromimetic; Thyroid hormone receptor beta (TRβ) agonist |
| Identifiers | |
| IUPAC name | |
| CAS Number | 2156649-32-8 |
| PubChem CID | 132160637 |
| DrugBank | DB18157 |
| ChemSpider | 129433137 |
| UNII | QTW4WC4BRX |
| KEGG | D13273 |
| ChEMBL | ChEMBL5314909 |
| Chemical and physical data | |
| Formula | C19H21Cl2NO3 |
| Molar mass | 382.28 g·mol−1 |
| 3D model (JSmol) | Interactive image |
| SMILES | |
| InChI | |
///////////elunetirom, ANAX LABS, thyroid hormone beta receptor agonist, ABX-002, MA-JD21, ABX 002, MA JD21, QTW4WC4BRX, MA-JD-21,
Elsovaptan
Elsovaptan
CAS 2296801-25-5
MFC19H20ClN5O2 MW385.8 g/mol
[(3S)-7-chloro-3-methyl-2,3-dihydro-1,4-benzoxazin-4-yl]-(6-pyrimidin-2-yl-2,6-diazaspiro[3.3]heptan-2-yl)methanone
[(3S)-7-chloro-3-methyl-2,3-dihydro-4H-1,4-benzoxazin-4-yl][6-(pyrimidin-2-yl)-2,6-diazaspiro[3.3]heptan-2-yl]methanone
vasopressin receptor antagonist, Alzheimer disease, T206306, Y2Z74WGU3J
Elsovaptan is a selective vasopressin receptor antagonist. It is primarily used in scientific research to study the modulation of vasopressin action, particularly in the context of neurodegenerative conditions like Alzheimer’s disease
- Primary Mechanism: Blocks the binding of vasopressin to its receptors, which typically disrupts fluid volume regulation and can lead to vasodilation.
Research Applications
Currently, Elsovaptan is designated as a research-use-only compound and is not approved for human therapeutic or veterinary use.
Its study is often linked to research on:
- Neurodegenerative Diseases: Investigating the role of the vasopressin system in the progression of Alzheimer’s disease.
- Fluid Regulation: Understanding how antagonizing vasopressin affects vascular resistance and blood pressure.
The compound has been listed in recent International Nonproprietary Names (INN) proposals by the World Health Organization (WHO) for pharmaceutical substances, indicating it is an active subject of pharmacological study
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References
/////////elsovaptan, ANAX LABS, vasopressin receptor antagonist, Alzheimer disease, T206306, Y2Z74WGU3J
Elisrasib
Elisrasib
CAS2914919-85-8
MFC32H35F6N7O3. MW 679.7 g/mol
2-[(2S)-4-[(7S)-7-[3-amino-2-fluoro-5-methyl-6-(trifluoromethyl)phenyl]-2-[[(2R,8S)-2-fluoro-1,2,3,5,6,7-hexahydropyrrolizin-8-yl]methoxy]-7,8-dihydro-5H-pyrano[4,3-d]pyrimidin-4-yl]-1-(2-fluoroprop-2-enoyl)piperazin-2-yl]acetonitrile
[(2S)-4-[(7S)-7-[3-amino-2-fluoro-5-methyl-6-(trifluoromethyl)phenyl]-2-{[(2R,7aS)-2-fluorotetrahydro-1Hpyrrolizin-7a(5H)-yl]methoxy}-7,8-dihydro-5H-pyrano[4,3-d]pyrimidin-4-yl]-1-(2-fluoroprop-2-enoyl)piperazin-2-yl]acetonitrile
Kirsten rat sarcoma viral oncogene homolog inhibitor, antineoplastic, D3S 001, PFW9YLB86H
Elisrasib (D3S-001) is a next-generation, orally available KRAS G12C inhibitor developed by D3 Bio that demonstrates high potency, sustained target engagement, and strong clinical activity in advanced solid tumors, including those resistant to first-generation inhibitors. As of April 2026, clinical trials show it has a 52% objective response rate (ORR) in G12C inhibitor-naive patients and a 30% ORR in refractory populations.
Key Aspects of Elisrasib (D3S-001):
- Mechanism of Action: It is a highly potent, covalent inhibitor that selectively binds the GDP-bound (inactive) form of the KRAS G12C mutant, effectively halting tumor cell proliferation and metastasis.
- Superior Efficacy: Preliminary data suggests elisrasib may be more potent than earlier inhibitors like sotorasib and adagrasib, providing higher target occupancy at lower doses.
- Clinical Performance (AACR 2026 Data):
- Naive Patients: 52% ORR, with a median duration of response (mDOR) of 16.5 months and median progression-free survival (mPFS) of 12.2 months at the 600 mg dose.
- Refractory Patients: 32% ORR, with a mDOR of 15.6 months and mPFS of 8.1 months.
- Targeted Cancers: Clinical trials are focused on KRAS G12C-mutant tumors, specifically non-small cell lung cancer (NSCLC), colorectal cancer (CRC), and other solid tumors.
- Safety Profile: The drug has shown good tolerability and a safe profile in early studies.
Elisrasib is in Phase 1/2 development and was highlighted for its promising results in treating patients with KRAS G12C-mutant tumors
Elisrasib is an orally bioavailable inhibitor of the oncogenic KRAS substitution mutation G12C, with potential antineoplastic activity. Upon oral administration, elisrasib selectively targets the KRAS G12C mutant and inhibits KRAS G12C-mediated signaling. This may halt proliferation and metastasis in susceptible tumor cells. KRAS, a member of the RAS family of oncogenes, serves an important role in cell signaling, division and differentiation. Mutations of KRAS may induce constitutive signal transduction leading to tumor cell proliferation, invasion, and metastasis.
- A Phase 1 Study to Assess Food Effect on the Pharmacokinetics of D3S-001 in Healthy Adult ParticipantsCTID: NCT07093398Phase: Phase 1Status: CompletedDate: 2026-03-25
- A Phase 1/2 Study of D3S-002 as Monotherapy or Combination Therapy in Adult Subjects With Advanced Solid Tumors With MAPK Pathway MutationsCTID: NCT05886920Phase: Phase 1/Phase 2Status: Active, not recruitingDate: 2026-03-23
- A Study of D3S-001 Monotherapy or Combination Therapy in Subjects With Advanced Solid Tumors With a KRAS p.G12C MutationCTID: NCT05410145Phase: Phase 1/Phase 2Status: RecruitingDate: 2026-03-12
PAT
SYN
Example 17
Step 6: Synthesis of Compound 17
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References
- Pyrimidoheterocyclic compounds and application thereofPublication Number: EP-4105211-A1Priority Date: 2020-03-12
- Pyrimidoheterocyclic compounds and application thereofPublication Number: US-2023151004-A1Priority Date: 2020-03-12
//////////elisrasib, anax labs, Kirsten rat sarcoma viral oncogene homolog inhibitor, antineoplastic, D3S 001, PFW9YLB86H
Elironrasib
Elironrasib
CAS 2641998-63-0
MFC55H78FN9O8 MW 1012.3 g/mol
1-[4-(dimethylamino)-4-methylpent-2-ynoyl]-N-[(2S)-1-[[(6S,8S,14S)-22-ethyl-21-[2-[(1S)-1-methoxyethyl]-3-pyridinyl]-18,18-dimethyl-9,15-dioxo-5,16-dioxa-2,10,22,28-tetrazapentacyclo[18.5.2.12,6.110,14.023,27]nonacosa-1(26),20,23(27),24-tetraen-8-yl]amino]-3-methyl-1-oxobutan-2-yl]-4-fluoro-N-methylpiperidine-4-carboxamide
- 1-[4-(dimethylamino)-4-methylpent-2-ynoyl]-N-[(2S)-1-[[(6S,8S,14S)-22-ethyl-21-[2-[(1S)-1-methoxyethyl]pyridin-3-yl]-18,18-dimethyl-9,15-dioxo-5,16-dioxa-2,10,22,28-tetrazapentacyclo[18.5.2.12,6.110,14.023,27]nonacosa-1(26),20,23(27),24-tetraen-8-yl]amino]-3-methyl-1-oxobutan-2-yl]-4-fluoro-N-methylpiperidine-4-carboxamide
- 3-Pyridazinecarboxylic acid, N1-[N-[[1-[4-(dimethylamino)-4-methyl-1-oxo-2-pentyn-1-yl]-4-fluoro-4-piperidinyl]carbonyl]-N-methyl-L-valyl-3-[4-[(2R)-1-ethyl-3-(3-hydroxy-2,2-dimethylpropyl)-2-[2-[(1S)-1-methoxyethyl]-3-pyridinyl]-1H-indol-5-yl]-2-morpholinyl]-L-alanyl]hexahydro-, (3–>2)-lactone, (3S)-
Kirsten rat sarcoma viral oncogene homolog inhibitor, antineoplastic, RMC-6291, RMC 6291, 942KVV5CJP
Elironrasib (RMC-6291) is an investigational, orally bioavailable, RAS(ON) G12C-selective inhibitor developed by Revolution Medicines that targets the active GTP-bound form of KRAS G12C. In Phase 1 trials, it showed significant promise in treating advanced KRAS G12C-mutated solid tumors, including non-small cell lung cancer (NSCLC). [1, 2, 3]
Key Clinical Trial Results (as of Oct 2025):
- Response Rate: 42% objective response rate (ORR).
- Disease Control: 79% disease control rate (DCR).
- Durability: Median duration of response was 11.2 months.
- Survival: Median progression-free survival was 6.2 months.
- Overcoming Resistance: Demonstrated efficacy in patients who had previously progressed on first-generation KRAS G12C(OFF) inhibitors.
Mechanism of Action:
Elironrasib acts as a covalent tri-complex inhibitor (TCI). It forms a complex with the intracellular chaperone protein cyclophilin A (CypA) and the active KRAS G12C(GTP) protein, effectively shutting down oncogenic signaling.
Development Status:
- Designation: It has received FDA breakthrough therapy designation for KRAS G12C-mutant NSCLC.
- Trials: Currently in Phase 1 clinical trials (e.g., NCT05462717) to evaluate safety, tolerability, and efficacy, both as a monotherapy and in combination.
- Target Population: Patients with KRAS G12C-addicted solid tumors.
Discovery of Elironrasib (RMC-6291), a Potent and Orally Bioavailable, RAS(ON) G12C-Selective, Covalent Tricomplex Inhibitor for the Treatment of Patients with RAS G12C-Addicted Cancers – PubMed27 Mar 2025 — This information does not constitute medical advice or diagnosis. Elirronrasib (RMC-6291) is a potent, orally bioavailable,
- Revolution Medicines to Present Updated Elironrasib Safety and Efficacy Data in Patients with KRAS G12C Non-Small Cell Lung Cancer Following Treatment with a KRAS(OFF) G12C Inhibitor22 Oct 2025 — This information does not constitute medical advice or diagnosis. Elirronrasib is a RAS(ON) G12C-selective inhibitor being develop…
Revolution Medicines
- Elironrasib May Overcome Resistance to Prior KRAS G12C Inhibition in Non-small Cell Lung Cancer
- OriginatorREVOLUTION Medicines
- ClassAntineoplastics; Morpholines; Piperidines; Pyridazines; Small molecules
- Mechanism of ActionKRAS protein inhibitors
- Phase I/IISolid tumours
- Clinical Phase UnknownNon-small cell lung cancer
- 30 Jan 2026Phase-I/II clinical trials in Solid tumours (Combination therapy, Late-stage disease, Metastatic disease) in USA (PO) (NCT07397338)
- 31 Oct 2025Elironrasib is still in phase I trial in Solid tumours (Late-stage disease, Metastatic disease, Monotherapy) in Australia, Italy, South Korea, Malaysia, Singapore, Spain, Czech Republic, Thailand and USA (PO, Tablet) (NCT05462717)
- 28 Oct 2025No recent reports of development identified for phase-I development in Solid-tumours(Late-stage disease, Metastatic disease, Monotherapy) in Australia, Italy, South Korea, Malaysia, Singapore, Spain, Czech Republic, Thailand (PO, Tablet)
Elironrasib is an orally bioavailable, covalent inhibitor of the active, guanosine triphosphate (GTP)-bound form of the oncogenic KRAS substitution mutation G12C, KRAS G12C(ON), with potential antineoplastic activity. Upon oral administration, elironrasib forms a tri-complex with the intracellular chaperone protein and immunophilin cyclophilin A (CypA) and KRAS G12C(ON). This tri-complex inhibits KRAS G12C(ON)-mediated signaling, which may inhibit tumor cell proliferation. KRAS, a member of the RAS family of oncogenes, serves an important role in cell signaling, division and differentiation. Mutations of KRAS may induce constitutive signal transduction leading to tumor cell growth, proliferation, invasion, and metastasis.
- Study of Elironrasib and Daraxonrasib as Monotherapies and Combination Therapy in Participants With Advanced KRAS G12C Mutant Solid TumorsCTID: NCT06128551Phase: Phase 1/Phase 2Status: RecruitingDate: 2026-04-23
- Dose Escalation and Dose Expansion Study of RMC-6291 Monotherapy in Subjects With Advanced KRASG12C Mutant Solid TumorsCTID: NCT05462717Phase: Phase 1Status: Active, not recruitingDate: 2026-04-08
- Study of RAS(ON) Inhibitors in Combination With Ivonescimab in Patients With Solid TumorsCTID: NCT07397338Phase: Phase 1/Phase 2Status: RecruitingDate: 2026-03-30
- Study of RAS(ON) Inhibitors in Patients With Advanced RAS-mutated NSCLCCTID: NCT06162221Phase: Phase 1/Phase 2Status: RecruitingDate: 2026-03-09
SYN
https://pubs.acs.org/doi/10.1021/acs.jmedchem.4c02313
SYN
PAT’
Part 5—Synthesis of Compound A—(12M)-1-(4-(dimethylamino)-4-methylpent-2 ynoyl)-N-((2S)-1-(((22S,63S,4S)-11-ethyl-12-(2-((S)-1-methoxyethyl)pyridin-3-yl)-10,10-dimethyl-5,7-dioxo-61,62,63,64,65,66-hexahydro-11H-8-oxa-2(4,2)-morpholina-1(5,3)-indola-6(1,3) pyridazinacycloundecaphane-4-yl)amino)-3-methyl-1-oxobutan-2 yl)-4-fluoro-N-methylpiperidine-4-carboxamide
| To a 50 L glass reactor was charged Compound 15 (1.91 kg, 1.0 eq) and DMF (13.9 kg). The mixture was agitated at 20-30° C. until all of the solids were dissolved. Compound 2 (1.70 kg, 1.2 eq) and DMF (3.8 kg) were charged. The mixture was agitated at 20-30° C. until all of the solids were dissolved. DIPEA (2.20 kg, 5.50 eq) was charged at 20-30° C. and the mixture was cooled to −20-−10° C. under agitation. Ethyl cyanoglyoxylate-2-oxime (Oxyma) (0.48 kg, 1.1 eq) was charged to the reactor and the reaction mixture was agitated at −20 to −10° C. for 30 min. PyBOP was charged as a DMF solution (1.89 kg dissolved in 3.62 kg DMF, 1.2 eq) to the reactor at −20 to −10° C. in </=1 h. The reaction mixture was agitated at −20 to −10° C. for 1-3 h. Reaction monitoring by HPLC showed the reaction was complete. |
| The crude product was then further purified by recrystallization with a mixture of EtOAc and n-Heptane to give purified Compound A as a white solid. |
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References
- Macrocyclic heterocycles and uses thereofPublication Number: US-2023339952-A1Priority Date: 2022-04-20
- Macrocyclic heterocycles and uses thereofPublication Number: WO-2023205701-A1Priority Date: 2022-04-20
- Methods for delaying, preventing, and treating acquired resistance to ras inhibitorsPublication Number: US-2023233569-A1Priority Date: 2020-06-18
- Ras inhibitorsPublication Number: US-2021130303-A1Priority Date: 2019-11-04
- Ras inhibitorsPublication Number: US-2023234929-A1Priority Date: 2019-11-04
- Ras inhibitors
- Publication Number: US-11566007-B2
- Priority Date: 2019-11-04
- Grant Date: 2023-01-31
////////elironrasib, ANAX LABS, Kirsten rat sarcoma viral oncogene homolog inhibitor, antineoplastic, RMC-6291, RMC 6291, 942KVV5CJP
Elecoglipron
Elecoglipron
CAS 3011682-49-5
MFC48H46F2N10O5 MW880.9 g/mol
3-[1-[2-[(4S)-2-(3-cyclopropyl-4-fluorophenyl)-3-[3-(4-fluoro-1-methylindazol-5-yl)-2-oxoimidazol-1-yl]-4-methyl-6,7-dihydro-4H-pyrazolo[4,3-c]pyridine-5-carbonyl]-7-[(4S)-2,2-dimethyloxan-4-yl]indolizin-3-yl]cyclopropyl]-4H-1,2,4-oxadiazol-5-one
- 1,2,4-Oxadiazol-5(2H)-one, 3-[1-[2-[[(4S)-2-(3-cyclopropyl-4-fluorophenyl)-3-[3-(4-fluoro-1-methyl-1H-indazol-5-yl)-2,3-dihydro-2-oxo-1H-imidazol-1-yl]-2,4,6,7-tetrahydro-4-methyl-5H-pyrazolo[4,3-c]pyridin-5-yl]carbonyl]-7-[(4S)-tetrahydro-2,2-dimethyl-2H-pyran-4-yl]-3-indolizinyl]cyclopropyl]-
- 3-(1-(2-((S)-2-(3-cyclopropyl-4-fluorophenyl)-3-(3-(4-fluoro-1-methyl-1H-indazol-5-yl)-2-oxo-2,3-dihydro-1H-imidazol-1-yl)-4-methyl-4,5,6,7-tetrahydro-2H-pyrazolo[4,3-c]pyridine-5-carbonyl)-7-((S)-2,2-dimethyltetrahydro-2H-pyran-4-yl)indolizin-3-yl)cyclopropyl)-1,2,4-oxadiazol-5(4H)-one
- 3-[1-[2-[(4S)-2-(3-cyclopropyl-4-fluorophenyl)-3-[3-(4-fluoro-1-methylindazol-5-yl)-2-oxoimidazol-1-yl]-4-methyl-6,7-dihydro-4H-pyrazolo[4,3-c]pyridine-5-carbonyl]-7-[(4S)-2,2-dimethyloxan-4-yl]indolizin-3-yl]cyclopropyl]-4H-1,2,4-oxadiazol-5-one
glucagon-like peptide 1 (GLP-1) receptor agonist, AZD 5004, ECC 5004, G94JJ74N5Y
Elecoglipron (AZD5004 / ECC-5004) is a glucagon-like peptide 1 (GLP-1) receptor agonist. In vitro, AZD5004/ECC5004 binds the human GLP-1 receptor with high affinity (IC₅₀ ~ 2.4 nM), drives G s-coupled cAMP signaling with low-nanomolar potency (EC₅₀ ~ 2–6 nM in HEK293/β-cell cAMP and GSIS assays), shows partial agonism in some cell systems without detectable β-arrestin recruitment or receptor internalization, and potentiates glucose-stimulated insulin secretion (EC₅₀ ~ 5.9 nM). In in vivo non-human primate studies, oral dosing produced robust pharmacodynamic effects — insulin secretion and glucose clearance with estimated EC₅₀ ~ 0.022 nM — and dose-dependent reductions in body-weight gain over long-term dosing, consistent with GLP-1-mediated metabolic effects
PAT
US-11584751-B1
https://patentscope.wipo.int/search/en/detail.jsf?docId=US392022131&_cid=P22-MOWB0S-70559-1
PAT
US-12037339-B2
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References
- Substituted imidazoles as GLP-1 receptor agonistsPublication Number: US-12037339-B2Priority Date: 2020-07-20Grant Date: 2024-07-16
- Substituted imidazoles as GLP-1 receptor agonistsPublication Number: US-11584751-B1Priority Date: 2020-07-20Grant Date: 2023-02-21
//////elecoglipron, anax labs, glucagon-like peptide 1 (GLP-1) receptor agonist, AZD 5004, ECC 5004, G94JJ74N5Y
Egalognastat
Egalognastat
CAS 1884154-02-2
MF C17H21N5O3S MW375.45
(S)-N-(5-(4-(1-(BENZO(D)(1,3)DIOXOL-5-YL)ETHYL)PIPERAZIN-1-YL)-1,3,4-THIA-DIAZOL-2-YL)ACETAMIDE
ACETAMIDE, N-(5-(4-((1S)-1-(1,3-BENZODIOXOL-5-YL)ETHYL)-1-PIPERAZINYL)-1,3,4-THIADIAZOL-2-YL)-
N-(5-{4-[(1S)-1-(2H-1,3-benzodioxol-5-yl)ethyl]piperazin-1-yl}-1,3,4-thiadiazol-2-yl)acetamide
O-GlcNAcase enzyme inhibitor, ASN90, ASN 90, E9QIS63WUM, ASN 120290
Egalognastat (ASN90) is a potent, selective, and brain-penetrant O-GlcNAcase (OGA) inhibitor (\(IC_{50} = 10.2 \text{ nM}\)). It acts as a disease-modifying agent in pre-clinical studies for neurodegenerative conditions by enhancing protein O-GlcNAcylation, which regulates tau and \(\alpha \)-synuclein pathology. Egalognastat is under investigation for diseases like Alzheimer’s and Parkinson’s.
Key Details on Egalognastat (ASN90):
- Mechanism: As a substrate-competitive OGA inhibitor, it binds to the OGA enzyme and reduces the removal of O-GlcNAc from proteins.
- Disease Targets: It is primarily studied for tauopathies and \(\alpha \)-synucleinopathies.
- Efficacy: Preclinical data shows it raises O-GlcNAcylation of brain proteins and has shown therapeutic potential in models of neurodegeneration.
- Distinction: Unlike earlier sugar-based inhibitors (like Thiamet G), Egalognastat is chemically distinct.
- Status: It is primarily used for research and preclinical development.
- Related Research: Recent studies (2025) have analyzed the potential synaptotoxic effects of OGA inhibitors, including Egalognastat (ASN90) and Ceperognastat, indicating that while they are effective for removing misfolded proteins, they may interfere with synaptic plasticity.
SYN
Publication Name: Journal of Medicinal Chemistry
Publication Date: 2024-08-07
PMID: 39109492
DOI: 10.1021/acs.jmedchem.4c01132
SYN
PAT
PAT
PAT
- Glycosidase inhibitorsPublication Number: US-12187741-B2Priority Date: 2014-08-28Grant Date: 2025-01-07
- Glucosidase inhibitorsPublication Number: ES-2893289-T3Priority Date: 2014-08-28Grant Date: 2022-02-08
- Glycosidase inhibitorsPublication Number: EP-3186243-B1Priority Date: 2014-08-28Grant Date: 2021-07-21
- Glycosidase inhibitorsPublication Number: US-10336775-B2Priority Date: 2014-08-28Grant Date: 2019-07-02
- Glycosidase inhibitorsPublication Number: US-11046712-B2Priority Date: 2014-08-28Grant Date: 2021-06-29
- Glycosidase inhibitorsPublication Number: EP-3868752-A1Priority Date: 2014-08-28
- Glycosidase InhibitorsPublication Number: CN-107108601-APriority Date: 2014-08-28
- Glycosidase inhibitorsPublication Number: US-2019367533-A1Priority Date: 2014-08-28
- Glycosidase inhibitorsPublication Number: WO-2016030443-A1Priority Date: 2014-08-28
- Glycosidase inhibitorsPublication Number: EP-3186243-A1Priority Date: 2014-08-28
- Glycosidase inhibitorPublication Number: JP-2019206554-APriority Date: 2014-08-28
- Glycosidase inhibitorsPublication Number: US-2017298082-A1Priority Date: 2014-08-28
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References
////////egalognastat, anax labs, O-GlcNAcase enzyme inhibitor, ASN90, ASN 90, E9QIS63WUM, ASN 120290
DR ANTHONY MELVIN CRASTO
ORGANIC SPECTROSCOPY
New Drug Approvals 
