Wednesday, 26 August 2026

Peturadol

 

Peturadol

CAS 686301-48-4

MFC12H20N6O MW264.33 g/mol

5-{[2-(6-amino-9H-purin-9-yl)ethyl]amino}pentan-1-ol
central analgesic, NB001, NB 001, HTS 09836, J89QT81NBQ

NB-001 has been investigated for the treatment of Recurrent Herpes Labialis.

NB001 (HTS 09836) is an adenylcyclase 1 (AC1) inhibitor which has effect on neural and non-neural pain by modulating AC1 activity

Peturadol (also known by its developmental code NB001) is a potent, selective, and orally active adenylyl cyclase 1 (AC1) inhibitor. It is primarily recognized as a specialized chemical compound used in advanced medical and pharmacological laboratory research.

Because drug names can sometimes look or sound very similar, please check the spelling carefully. If you are looking for a medication prescribed to you by a doctor, it is highly likely you mean Patradol (a combination painkiller containing tramadol and paracetamol) or Pentadol / Tapentadol (an opioid analgesic).

Clinical Trial

NCT NumberSponsorConditionStart DatePhase
NCT01324466NanoBio CorporationRecurrent Herpes Labialis2011-04PHASE3
NCT05290493Nobias Therapeutics, Inc.22q11 Deletion Syndrome2022-02-10PHASE2
NCT01695187NanoBio CorporationHerpes Labialis2012-10PHASE3
NCT01321359NanoBio CorporationRecurrent Herpes Simplex Labialis2011-04PHASE3
NCT00453401NanoBio CorporationHerpes Labialis2007-02PHASE2
  • NB-001 in Children and Adolescents With 22q11 Deletion SyndromeCTID:NCT05290493Phase:Phase 2Status:CompletedDate:2025-02-10
  • NB-001 Treatment of Recurrent Herpes LabialisCTID:NCT01695187Phase:Phase 3Status:Unknown statusDate:2013-06-14
  • A Multicenter Study of NB-001 in the Treatment of Recurrent Herpes Labialis (SHaRCS)CTID:NCT01324466Phase:Phase 3Status:CompletedDate:2013-05-23
  • Safety, Pharmacokinetics, and Efficacy Study of NB-001 to Treat Recurrent Herpes LabialisCTID:NCT00453401Phase:Phase 2Status:CompletedDate:2008-05-30

PAT

https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2007041863&_cid=P22-MSFGZW-54602-1

PAT

https://patentscope.wipo.int/search/en/detail.jsf?docId=US210409779&_cid=P22-MSFGZW-54602-1

Synthesis and Purification of Intermediate 2

      The compound 1 (20.00 g, 111.62 mmol, 1.00 eq) was dissolved in dioxane (600.00 mL), and then SOCl 2 (26.56 g, 223.24 mmol, 16.20 mL, 2.00 eq) was slowly added to the afore-mentioned reaction solution, and the mixture was continuously stirred at 100° C. for 4 hours. The LCMS assay showed the raw materials are reacted completely and the desired product was generated. The solvent in the reaction solution was removed under reduced pressure in a water pump. The gray residue was added into 100 ml of ethanol and stirred for 10 minutes. The mixture was filtered through a sintered glass funnel. 100 ml of saturated sodium carbonate solution was added to the filtered solid and stirred for 20 minutes. The mixture was filtered through a sintered glass funnel. The filtered solid was spin-dried in a water pump under reduced pressure to obtain crude intermediate 2 (19.60 g, 98.59 mmol, with a yield of 88.32% and a purity of 99.4%), and the product is directly used in the next step without further purification.

(2) Synthesis and Purification of NB001

      The compound 2 (19.60 g, 99.18 mmol, 1.00 eq) was dissolved in n-BuOH (390.00 mL), and then the compound 3 (30.69 g, 297.54 mmol, 3.00 eq) was slowly added to the afore-mentioned reaction solution, and the mixture was continuously stirred at 110° C. for 18 hours. The LCMS assay showed the raw materials are reacted completely and the desired product was generated. The solvent was removed under reduced pressure through a water pump, and the residue was concentrated to obtain a yellow crude product. 196 ml of DMF was added into the yellow crude product, then the mixture was continuously stirred at −40° C. for 1 hour. Then the mixture was filtered through a sintered glass funnel. 200 ml of ethyl acetate was added into the filtered solid, and the mixture was filtered again to obtain an off-white solid NB001 (19.74 g, 71.38 mmol, with a yield of 71.97% and a purity 95.587%).

PAT

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References

[1]. Min Zhuo. Method for treating neuronal and non-neuronal pain. US8124599B2.

[2]. Wang H, et al., Identification of an adenylyl cyclase inhibitor for treating neuropathic and inflammatory pain. Sci Transl Med. 2011 Jan 12;3(65):65ra3. [Content Brief]

[3]. Zhou Z, et al., Inhibition of calcium-stimulated adenylyl cyclase subtype 1 (AC1) for the treatment of pain and anxiety symptoms in Parkinson's disease mice model. Mol Pain. 2024 Jan-Dec;20:17448069241266683. [Content Brief]

////////////peturadol, anax labs, central analgesic, NB001, NB 001, HTS 09836, J89QT81NBQ

#peturadol, #anax labs, #central analgesic, #NB001, #NB 001, #HTS 09836, #J89QT81NBQ

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Plodicitinib

Plodicitinib

CAS 2360992-48-7

MF C19H22FN7O2 MW399.42

1-[(3S,4R)-3-[[2-[(1-ethylpyrazol-4-yl)amino]-7H-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]-4-fluoropiperidin-1-yl]prop-2-en-1-one

1-[(3S,4R)-3-({2-[(1-ethyl-1H-pyrazol-4-yl)amino]-7Hpyrrolo[2,3-d]pyrimidin-4-yl}oxy)-4-fluoropiperidin-1-yl]prop2-en-1-one
Janus tyrosine kinase 3/TEC family kinase inhibitor, antiinflammatory, veterinary, SX5UEP3JXA

Plodicitinib is a Janus tyrosine kinase 3/TEC family kinase inhibitor with anti-inflammatory activity.

Plodicitinib is a small-molecule, dual Janus tyrosine kinase 3 (JAK3) and TEC family kinase (specifically BTK) inhibitor that exhibits strong anti-inflammatory properties.

Mechanism of Action

The compound blocks specific enzymatic pathways involved in cellular signaling:

  • JAK3 Inhibition: It targets Janus kinase 3, which plays an essential role in transmitting signals for cytokines that regulate immune cell development and activation.
  • TEC/BTK Inhibition: It blocks Bruton's tyrosine kinase (BTK), a component vital for B-cell development and activation. [1, 2]
  • Combined Effect: By blocking these pathways, it suppresses the overactive immune and inflammatory responses that drive autoimmune and allergic conditions.

Applications and Development Status

  • Veterinary Medicine: In early 2026, Daewoong Pharmaceutical submitted an application to the Animal and Plant Quarantine Agency in South Korea for commercial approval of plodicitinib. It is being positioned as a specialized, companion animal-only treatment to manage atopic dermatitis in dogs.
  • Research Use: In the scientific community, it is actively utilized as a laboratory tool compound to study kinase signaling pathways and inflammatory disease models.

PAT

https://patentscope.wipo.int/search/en/detail.jsf?docId=US306969271&_cid=P22-MSL6QJ-67927-1

Example 4: Preparation of 1-(cis-3-((2-((1-ethyl-1H-pyrazol-4-yl)amino)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)oxy)-4-fluoropiperidin-1-yl)prop-2-en-1-one

19.3 mg (yield: 27.8%) of the title compound was obtained in the same manner as in Example 1, except that cis-tert-butyl-4-fluoro-3-hydroxypiperidine-1-carboxylate was used instead of trans-tert-butyl-4-fluoro-3-hydroxypiperidine-1-carboxylate in Example 1.

Example 5: Preparation of 1-((3S,4R)-3-((2-((1-ethyl-1H-pyrazol-4-yl)amino)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)oxy)-4-fluoropiperidin-1-yl)prop-2-en-1-one

16.2 mg (yield: 57.4%) of the title compound was obtained in the same manner as in Example 1, except that tert-butyl(3S,4R)-4-fluoro-3-hydroxypiperidine-1-carboxylate was used instead of trans-tert-butyl-4-fluoro-3-hydroxypiperidine-1-carboxylate in Example 1.
      1H NMR (500 MHz, CD 3OD) δ 7.98 (s, 1H), 7.57-7.55 (m, 1H), 6.88-6.45 (m, 2H), 6.30-5.98 (m, 2H), 5.80-5.44 (m, 2H), 5.20-5.05 (m, 1H), 4.40-4.12 (m, 3H), 4.05-3.52 (m, 3H), 2.24-2.21 (m, 1H), 2.01-1.94 (m, 1H), 1.47-1.43 (m, 3H)

Example 25: Preparation of 1-((3S,4S)-3-((2-((1-ethyl-1H-pyrazol-4-yl)amino)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)oxy)-4-fluoropiperidin-1-yl)prop-2-en-1-one

The compound of Example 1 was separated by CHIRALCEL OZ-H column to obtain the title compound with an analysis time of 10.1 minutes.
1H NMR (500 MHz, CD 3OD) δ 7.98-7.95 (m, 1H), 7.57-7.55 (m, 1H), 6.84-6.53 (m, 2H), 6.26-6.08 (m, 2H), 5.78-5.52 (m, 1H), 5.41-5.40 (m, 1H), 5.10-5.04 (m, 1H), 4.50-4.06 (m, 4H), 3.89-3.86 (m, 1H), 3.55-3.50 (m, 1H), 2.19-2.16 (m, 1H), 1.95-1.94 (m, 1H), 1.45-1.41 (m, 3H)

PAT

https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2025121903&_cid=P22-MSL6W2-73218-1

1-((3S,4R)-3-((2-((1-ethyl-1H-pyrazole-4-yl)amino)-7H-pyrrolo[2,3-d]pyrimidine-4-yl)oxy)-4-fluoropiperidin-1-yl)prop-2-en-1-one is represented by the following chemical formula 1:

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References

/////////anax labs, plodicitinib, Janus tyrosine kinase 3/TEC family kinase inhibitor, antiinflammatory, veterinary, SX5UEP3JXA

#anax labs, #plodicitinib, #Janus tyrosine kinase 3/TEC family kinase inhibitor, #antiinflammatory, #veterinary, #SX5UEP3JXA

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Tuesday, 25 August 2026

Prifetrastat

 

Prifetrastat

CAS 2569008-99-5

MFC19H18N4O5S MW414.4 g/mol

N-(6-((1H-Pyrazol-1-yl)methyl)-4-methoxybenzo[d]isoxazol-3-yl)-2-methoxybenzenesulfonamide

2-methoxy-N-{4-methoxy-6-[(1H-pyrazol-1-yl)methyl]-1,2-benzoxazol-3-yl}benzene-1-sulfonamide
antineoplastic, PF-07248144, PF 07248144, Solid tumours, CANCER, KAT6-IN-1, GN6DU4ZE30

Prifetrastat is an inhibitor of MYST histone acetyltransferase (HAT) KAT6, with potential antineoplastic activity. Upon administration, prifetrastat targets and binds to KAT6, and inhibits the acetylation of histones and other nonhistone substrates. This may disrupt gene expression and inhibit the proliferation of tumors that overexpress KAT6. KAT6A (MOZ; MYST3) and KAT6B (MORF; MOZ2; MYST4), commonly amplified genes in solid tumors, play key roles in cell cycle regulation and in tumorigenesis.

Prifetrastat (also known as PF-07248144) is an investigational, first-in-class small molecule drug that acts as a selective inhibitor of the epigenetic modifiers KAT6A and KAT6B. It is primarily studied as an antineoplastic agent for hormone receptor-positive (ER+/HER2–) advanced or metastatic breast cancer.

Mechanism of Action

  • Inhibits KAT6A and KAT6B histone acetyltransferases to block abnormal tumor cell growth.
  • Suppresses lineage-specific gene expression tied to estrogen receptor signaling and drug resistance.
  • Induces cell cycle arrest and tumor senescence.

Clinical Development

  • Evaluated in clinical trials (such as phase 1/2 and phase 3 evaluations) for patients whose breast cancer progressed after prior endocrine therapy and CDK4/6 inhibitors.
  • Commonly tested in combination regimens alongside anti-estrogen therapies like fulvestrant

Prifetrastat (also known as PF-07248144) is an investigational, first-in-class small molecule drug that acts as a selective inhibitor of the epigenetic modifiers KAT6A and KAT6B. It is primarily studied as an antineoplastic agent for hormone receptor-positive (ER+/HER2–) advanced or metastatic breast cancer.

Mechanism of Action

  • Inhibits KAT6A and KAT6B histone acetyltransferases to block abnormal tumor cell growth.
  • Suppresses lineage-specific gene expression tied to estrogen receptor signaling and drug resistance.
  • Induces cell cycle arrest and tumor senescence.

Clinical Development

  • Evaluated in clinical trials (such as phase 1/2 and phase 3 evaluations) for patients whose breast cancer progressed after prior endocrine therapy and CDK4/6 inhibitors.
  • Commonly tested in combination regimens alongside anti-estrogen therapies like fulvestrant
  • Phase IIIHER2 negative breast cancer
  • Phase IISolid tumours
  • No development reportedBreast cancer
  • 07 Aug 2026Prifetrastat is still in phase II development in Solid-tumours (Combination therapy, Late-stage disease, Metastatic disease, Second-line therapy or greater) in USA, Australia, Japan, China, South Korea (PO, Tablet) (NCT04606446)
  • 07 Aug 2026Prifetrastat is still in phase II development in Solid-tumours (Monotherapy, Late-stage disease, Metastatic disease, Second-line therapy or greater) in USA, Australia, Japan, China, South Korea (PO, Tablet) (NCT04606446)
  • 28 Jul 2026No recent reports of development identified for phase-I development in Breast-cancer(Metastatic disease) in USA (PO)

PAT

[WO2020254946]

https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2020254946&_cid=P12-MSO1IP-41527-1

Example 45: Preparation of 2-methoxy-N-{4-methoxy-6-[(1H-pyrazol-1-yl)methyl]-1,2-benzoxazol-3-yl}benzene-1-sulfonamide according to Scheme C (Route A).

To a suspension of 4-methoxy-6-[(1H-pyrazol-1-yl)methyl]-1,2-benzoxazol-3-amine (A-2) (2.5 g, 10 mmol) in pyridine (8.0 mL) was added 2-methoxybenzene-1-sulfonyl chloride (3.17 g, 15.4 mmol). The reaction was stirred at 120 °C for 1.5 h. The mixture was cooled to room temperature and diluted with MeOH. The resulting suspension was filtered. and the filter cake was washed with MeOH (30 mL). The solids were dissolved in DCM (50 mL) and MeOH (30 mL) was added. The DCM was removed under vacuum

and the precipitate was collected by filtration. The filter cake was dried by lyophilization to provide 2-methoxy-N-{4-methoxy-6-[(1H-pyrazol-1-yl)methyl]-1,2-benzoxazol-3-yl}benzene-1-sulfonamide (Example 45) (2.5 g, 59% yield) as a white solid. 1 H NMR (400 MHz, DMSO-d6) d 10.18 (s, 1H), 7.87 (d, J= 2.0 Hz, 1H), 7.80 (dd, J=1.6, 7.9 Hz, 1H), 7.66– 7.59 (m, 1H), 7.49 (d, J=1.5 Hz, 1H), 7.19 (d, J=8.3 Hz, 1H), 7.09 (t, J=7.7 Hz, 1H), 6.83 (s, 1H), 6.74 (s, 1H), 6.30 (t, J=2.0 Hz, 1H), 5.44 (s, 2H), 3.82 (s, 3H), 3.78 (s, 3H); m/z (ESI+) 415.0 (M+H) + .

Example 45: Alternative preparation of 2-methoxy-N-{4-methoxy-6-[(1H-pyrazol-1-yl)methyl]-1,2-benzoxazol-3-yl}benzene-1-sulfonamide according to Scheme D.

A 100 mL reactor equipped with an overhead stirrer was charged with 4-methoxy-6-(1H-pyrazol-1-ylmethyl)-1,2-benzoxazol-3-amine (A-2) (10.00 g, 40.94 mmol), 2-methoxybenzenesulfonyl chloride (10.15 g, 49.13 mmol), and acetonitrile (100 mL). The resulting suspension was stirred at 25 °C for 55 minutes. Via pipette, dimethylsulfoxide (0.36 mL, 4.09 mmol) was added in one portion. Via syringe, 3,5-lutidine (14.8 mL, 122.82 mmol) was added dropwise over 15 minutes. The resulting light-yellow suspension was stirred at 25 °C for 18 hours to reach >98% conversion as judged by LCMS. The reaction mixture was acidified with 1 M aq. HCl (100 mL), then

concentrated to ~80 mL (rotary evaporator, 40 °C, 85 mbar). The slurry was treated with additional 1 M aq. HCl (40 mL) to rinse down the walls of the vessel, then stirred at 20 °C for 2.5 hours. The resulting precipitate was collected by suction filtration. The filter cake was washed with water (2 x 50 mL), then dried under vacuum at 35 °C for 48 hours, affording crude 2-methoxy-N-{4-methoxy-6-[(1H-pyrazol-1-yl)methyl]-1,2-benzoxazol-3-yl}benzene-1-sulfonamide (Example 45) (15.2 g, 90% yield, 98% purity by LCMS) as a solid. m/z 415.1 (M+H) + .

To purify the crude product, a suspension of crude 2-methoxy-N-{4-methoxy-6-[(1H-pyrazol-1-yl)methyl]-1,2-benzoxazol-3-yl}benzene-1-sulfonamide (Example 45) (14.00 g, 33.78 mmol) in dichloromethane (210 mL) was heated in a 40 °C bath until a clear solution was obtained (10 minutes). The mixture was filtered, and the filtrate returned to a clean reaction vessel, using additional dichloromethane (70 mL) to quantitate the transfer. Ethyl acetate (140 mL) was added to the solution over 2 minutes, then the mixture stirred for 2.5 hours. No crystallization was observed, so the solution was concentrated under reduced pressure (200 mbar) to remove dichloromethane (volume was reduced by about 70 mL). More ethyl acetate (140 mL) was added to the residue, and the mixture stirred at room temperature for 21 hours. The resulting suspension was concentrated under reduced pressure (40 °C, 200 mbar) to about 280 mL, then stirred at room temperature for 3 hours. The solids were collected by filtration, with additional ethyl acetate (70 mL) used to rinse the reaction vessel and filter cake. The filter cake was dried in a vacuum oven at 35 °C for 23 hours, affording 2-methoxy-N-{4-methoxy-6-[(1H-pyrazol-1-yl)methyl]-1,2-benzoxazol-3-yl}benzene-1-sulfonamide (Example 45) (12.0 g, 85% yield, 97.9% purity by UPLC, no single impurity larger than 0.5%) as a solid. m/z 415.1 (M+H) + .

To purify further, a suspension of 2-methoxy-N-{4-methoxy-6-[(1H-pyrazol-1-yl)methyl]-1,2-benzoxazol-3-yl}benzene-1-sulfonamide (Example 45) (2.0 g, 4.73 mmol) in acetone (80 mL) was heated to reflux (bath temperature 55 °C) with stirring for 2 hours. While the mixture was still heated, ethyl acetate (30 mL) was added slowly, so that the internal temperature remained above 45 °C. The resulting slurry was concentrated to about 30 mL under mild vacuum (bath temp 65 °C), then cooled slowly at a rate of 1 °C/min to 20 °C (~31 minutes). The resulting precipitate was collected by suction filtration. The filter cake dried under vacuum at 50 °C for 22 hours, yielding 2-methoxy-N-{4-methoxy-6-[(1H-pyrazol-1-yl)methyl]-1,2-benzoxazol-3-yl}benzene-1-sulfonamide (Example 45) (1.825 g, 93% yield, 99.5% purity by UPLC) as a crystalline solid. 1 hour

NMR (400 MHz, CHLOROFORM-d) d 8.14 (dd, J=1.7, 7.8 Hz, 1H), 8.04 (s, 1H), 7.59 -7.51 (m, 2H), 7.44 (d, J=2.2 Hz, 1H), 7.14 - 7.06 (m, 1H), 6.95 (d, J=8.3 Hz, 1H), 6.78 (d, J=0.6 Hz, 1H), 6.45 (s, 1H), 6.32 (t, J=2.1 Hz, 1H), 5.38 (s, 2H), 3.97 (s, 3H), 3.91 (s, 3H).

PAT

US20250122182, Example 45,

PAT

https://patentscope.wipo.int/search/en/detail.jsf;jsessionid=EB10EA12C4409E47C6165613EF765C49.wapp1nC?docId=WO2026003716&_cid=P12-MSO1HW-40533-1

Scheme 1

Step 2

In an inerted reactor were added 6-((1 H-pyrazol-1-yl)methyl)-4-methoxybenzo[d]isoxazol-3-amine (lnt-4, 27.5 Kg, 112.6 mol, 1 equiv.), 2-methoxybenzenesulfonyl chloride (lnt-5, 33.9 Kg, 168.9 mol, 1.5 equiv.) and THF (248 L, 9-L/Kg). A solution of sodium te/Y-butoxide in THF (2 M, 197 L, 394.1 mol, 3.5 eq.) was added to the stirred mixture at 20 °C over 4 h. At the end of the addition the line was rinsed with THF (27.5 L, 1 L/Kg) and the mixture stirred for a further 1 h. Following reaction completion water (413 L, 15 L/Kg) was added at once followed by slow addition of aq. HCI (2 M, 197 L, 394.1 mol, 3.5 equiv.). The mixture was left stirring overnight, then the slurry was filtered, washed twice with CH3OH (82.5 L, 3 L/Kg) and dried to afford the title compound as a white solid (42.32 Kg, 90.6% yield).

1H NMR (400 MHz, DMSO) 5 10.09 (s, 1 H), 7.87 (dd, J = 2.3, 0.7 Hz, 1 H), 7.81 (dd, J = 7.8, 1.7 Hz, 1 H), 7.63 (ddd, J = 8.4, 7.4, 1.7 Hz, 1 H), 7.50 (dd, J = 1.8, 0.7 Hz, 1 H), 7.10 (td, J = 7.6, 1 .0 Hz, 1 H), 6.84 (d, J = 1 .0 Hz, 1 H), 6.30 (t, J = 2.1 Hz, 1 H), 5.44 (s, 2H), 3.83 (s, 3H), 3.79 (s, 3H). 13C NMR (101 MHz, DMSO) 5 164.82, 156.92, 154.39, 151.76, 144.13, 139.80, 135.73, 131.03, 130.43, 127.66, 120.52, 113.34, 106.25, 106.17, 104.42, 101.33, 56.51, 56.42, 55.01. HRMS: Ci9Hi8N4O5S+ [M+1 ]+ calculated:

415.1072; measured: 415.1071.

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References

///////////prifetrastat, anax labs, antineoplastic, PF-07248144, PF 07248144, Solid tumours, CANCER, KAT6-IN-1, GN6DU4ZE30

#prifetrastat, #anax labs, #antineoplastic, #PF-07248144, #PF 07248144, #Solid tumours, #CANCER, #KAT6-IN-1, #GN6DU4ZE30

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Pruvonertinib

 

Pruvonertinib

CAS 2064269-82-3

MF C27H32N8O2 MW500.6 g/mol

N-[2-[2-(dimethylamino)ethyl-methylamino]-4-methoxy-5-[[4-(8-methylimidazo[1,2-a]pyridin-3-yl)pyrimidin-2-yl]amino]phenyl]prop-2-enamide

N-(2-{2-(dimethylamino)ethylamino}-4-methoxy-5-{[4-(8-methylimidazo[1,2-a]pyridin-3-yl)pyrimidin-2-yl]amino}phenyl)prop2-enamide
epidermal growth factor receptor tyrosine kinase inhibitor, antineoplastic, YK-029A, YK 029A, HXJ9459HFK

Pruvonertinib is an orally bioavailable, mutant-selective, third-generation epidermal growth factor receptor (EGFR) inhibitor, with potential antineoplastic activity. Upon oral administration, pruvonertinib targets, binds to and inhibits the activity of EGFR with exon 20 insertion (Ex20ins) activating mutations, the gatekeeper mutation T790M and some other rare mutations, thereby preventing EGFR-mediated signaling. This may both induce cell death and inhibit tumor growth in EGFR-overexpressing tumor cells. EGFR, a receptor tyrosine kinase mutated in many tumor cell types, plays a key role in tumor cell proliferation and tumor vascularization.

Pruvonertinib (also known by its development code YK-029A) is an investigational, orally bioavailable, mutant-selective, third-generation epidermal growth factor receptor (EGFR) tyrosine kinase inhibitor. Developed by Puhe Pharmaceutical, it is designed as an antineoplastic agent primarily targeting advanced non-small cell lung cancer (NSCLC) with specific resistant mutations.

Mechanism of Action

  • Target Specificity: Binds selectively to mutant forms of EGFR.
  • Resistance Targeting: Inhibits the gatekeeper T790M mutation and exon 20 insertion (Ex20ins) mutations.
  • Scaffold Lineage: Structurally derived as an analogue of the established oncology drug osimertinib.
  • Tumour Regression: Blockades downstream EGFR-mediated signaling to induce cell death and stunt tumor vascularization.

Clinical Development & Indications

  • Primary Indication: Treatment of advanced, metastatic, or biomarker-positive Non-Small Cell Lung Cancer (NSCLC).
  • Development Status: Pre-commercial asset undergoing active clinical trial screening and testing evaluations.
  • Regulatory Track: Listed under the World Health Organization (WHO) Proposed International Nonproprietary Names (INN) List 132.

SYN

Analogue 6

Discovery of YK-029A, a novel mutant EGFR inhibitor targeting both T790 M and exon 20 insertion mutations, as a treatment for NSCLC

Publication Name:European Journal of Medicinal Chemistry, Publication Date:2023-10-05

PMID:37406381DOI:10.1016/j.ejmech.2023.115590

PAT

https://patentscope.wipo.int/search/en/detail.jsf?docId=US298712718&_cid=P10-MSQW7F-15668-1

N-(2-methoxy-4-(N 1,N 2,N 2-trimethyl-1,2-ethylenediamine-1-yl)-5-acrylamidephenyl)-4-(8-methylimidazo[1,2-a]pyridin-3-yl)pyrimidin-2-amine (hereinafter referred to as “Compound 1”) is a novel EGFR inhibitor represented by Formula (I):

The above compound is described in Chinese Patent Application 201610679161.7, and the content of which can be used as a reference for the present application

Step 7: Preparation of Drug Substance H (i.e. Compound 1)

Intermediate F (1.01 kg, 2.26 mol) was added to a mixed solution of acetonitrile (4.73 kg) and water (1.52 kg), and the temperature was lowered to 0 to 5° C. 3-Chloropropionyl chloride (373 g, 2.94 mol) was added dropwise. After the addition, the mixture was stirred at 0˜5° C. for 0.5 h. The completion of the reaction was detected.
      An aqueous solution of sodium hydroxide (sodium hydroxide: 290 g, 7.24 mol; purified water: 505 g) was added dropwise, and the reaction was heated to 65˜75° C. and stirred for 2˜3 h. The completion of the reaction was detected. The reaction system was cooled to 25-35° C., and purified water (4040 g) was added dropwise. Seed crystals were added and the mixture was stirred for 1˜2 h. Purified water (6060 g) was added dropwise. After the addition, the temperature was lowered to 5-10° C., and the mixture was stirred for 1˜2 h and filtered. The filter cake was rinsed with a mixed solvent of acetonitrile (1.6 kg) and purified water (4 kg), and then dried to give 900 g of the drug substance H with a purity of 97.8%. Yield: 79%.
      LCMS, m/z (ES+)(M+H +) 501.2,
       1HNMR (400 MHz, d 6-DMSO) δ 10.11 (s, 1H), 9.67 (d, J=5.8 Hz, 1H), 8.64 (s, 1H), 8.57 (s, 1H), 8.53 (s, 1H), 8.35 (d, J=5.4 Hz, 1H), 7.32 (d, J=5.4 Hz, 1H), 7.24 (d, J=6.9 Hz, 1H), 7.06 (s, 1H), 6.80 (t, J=6.9 Hz, 1H), 6.41 (dd, J=16.9, 10.1 Hz, 1H), 6.18 (dd, J=16.9, 1.9 Hz, 1H), 5.73 (dd, J=10.1, 1.9 Hz, 1H), 3.79 (s, 3H), 2.91 (t, J=5.7 Hz, 2H), 2.75 (s, 3H), 2.54 (s, 3H), 2.34 (t, J=5.8 Hz, 2H), 2.21 (s, 6H).

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References

/////////pruvonertinib, anax labs, epidermal growth factor receptor tyrosine kinase inhibitor, antineoplastic, YK-029A, YK 029A, HXJ9459HFK

#pruvonertinib, #anax labs, #epidermal growth factor receptor tyrosine kinase inhibitor, #antineoplastic, #YK-029A, #YK 029A, #HXJ9459HFK

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