Perzebertinib, Bizrolertinib

 

Perzebertinib, Bizrolertinib

CAS 2414056-31-6

MFC27H26F2N8O3 MW548.5 g/mol

5-[(4R)-3,3-difluoro-1-methylpiperidin-4-yl]oxy-6-methoxy-N-[3-methyl-4-([1,2,4]triazolo[1,5-c]pyrimidin-7-yloxy)phenyl]quinazolin-4-amine

• 4-Quinazolinamine, 5-[[(4R)-3,3-difluoro-1-methyl-4-piperidinyl]oxy]-6-methoxy-N-[3-methyl-4-([1,2,4]triazolo[1,5-c]pyrimidin-7-yloxy)phenyl]-
• 5-[[(4R)-3,3-Difluoro-1-methyl-4-piperidinyl]oxy]-6-methoxy-N-[3-methyl-4-([1,2,4]triazolo[1,5-c]pyrimidin-7-yloxy)phenyl]-4-quinazolinamine

5-{[(4R)-3,3-difluoro-1-methylpiperidin-4-yl]oxy}-6-methoxy-N-{3-methyl-4-[([1,2,4]triazolo[1,5-c]pyrimidin-7-yl)oxy]phenyl}quinazolin4-amine
epidermal growth factor receptor tyrosine kinase inhibitor, antineoplastic, ZN-A-1041, ZN 1041, RG 6596, Bizrolertinib, UN8TM5120C

Perzebertinib (also known as bizrolertinib or by developmental codes ZN-A-1041, ZN-1041, and RG6596) is an orally active, potent, and highly selective HER2 (ERBB2) tyrosine kinase inhibitor (TKI) designed to treat advanced solid tumors, primarily HER2-positive breast cancer.

Mechanism of Action

Perzebertinib functions as a selective, irreversible inhibitor of the HER2 tyrosine kinase. It blocks the ATP-binding site of the receptor to stop autophosphorylation. This action shuts down downstream signaling via the PI3K/AKT and MAPK pathways, successfully suppressing the growth, survival, and migration of tumor cells overexpressing HER2.

Key Clinical Advantages

• Blood-Brain Barrier (BBB) Penetration: The drug is designed to cross the blood-brain barrier effectively. This makes it highly valuable for treating brain metastases, a common and aggressive complication in advanced HER2-positive breast cancers.
• EGFR Sparing: Unlike older pan-EGFR/HER2 inhibitors, perzebertinib is engineered to spare wild-type EGFR. Sparing EGFR helps minimise common on-target side effects like severe skin rash and diarrhea.
• Efflux Resistance: It is not a substrate for P-gp or BCRP efflux pumps, allowing it to maintain high concentrations within central nervous system (CNS) tissues.

Development and Clinical Status

Initially discovered and developed by Suzhou Zanrong Pharmaceutical Technology (Zion Pharma), the asset is being co-developed in partnership with Roche and Genentech.

The drug has progressed through Phase 1 clinical studies evaluating its safety and pharmacokinetics in advanced solid tumors, moving forward into Phase 2/3 evaluations for HER2-positive advanced or locally advanced metastatic breast cancer. It is frequently evaluated as a monotherapy or in combination regimens alongside established therapies like capecitabine, trastuzumab, or pertuzumab

PAT

US11723908, Example 37, EG 77

https://patentscope.wipo.int/search/en/detail.jsf?docId=US344952565&_cid=P10-MS9QYW-06569-1

PAT

https://patentscope.wipo.int/search/en/detail.jsf;jsessionid=34DD4AB27E9264643AB08F2936B38B1B.wapp1nA?docId=EP476958262&_cid=P10-MS9QXM-05913-1

 International Patent Publication No. WO 2020/057511 A1, which is incorporated herein by reference in its entirety, discloses quinazoline compounds that inhibit type I receptor tyrosine kinases, demonstrate good brain penetration in animals, and possess favorable toxicity profiles (for example a decreased activity against hERG), and thus particularly useful in the treatment of type I receptor tyrosine kinases mediated diseases or conditions, in particular ErbB2-associated disease or conditions, including cancer (e.g., metastatic cancer, such as brain metastases). A specific compound, which is identified as (R)-N-(4-([1,2,4]triazolo[1,5-c]pyrimidin-7-yloxy)-3-methylphenyl)-5-((3,3-difluoro-1-methylpiperidin-4-yl)oxy)-6-methoxyquinazolin-4-amine (also referred to as compound (I) herein),

PAT

WO2020057511

https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2020057511&_cid=P10-MS9R3W-09545-1

Example 32

[0681]

(S) -N- (4- ( [1, 2, 4] triazolo [1, 5-c] pyrimidin-7-yloxy) -3-methylphenyl) -5- ( (3, 3-difluoro-1-methylpiperidin-4-yl) oxy) -6-methoxyquinazolin-4-amine

Step 5: (R) -N- (4- ( [1, 2, 4] triazolo [1, 5-c] pyrimidin-7-yloxy) -3-methylphenyl) -5- ( (3, 3-difluoro-1-methylpiperidin-4-yl) oxy) -6-methoxyquinazolin-4-amine and

[0696]

(S) -N- (4- ( [1, 2, 4] triazolo [1, 5-c] pyrimidin-7-yloxy) -3-methylphenyl) -5- ( (3, 3-difluoro-1-methylpiperidin-4-yl) oxy) -6-methoxyquinazolin-4-amine

[0697]

[0698]

To a solution of 4-chloro-5- ( (3, 3-difluoro-1-methylpiperidin-4-yl) oxy) -6-methoxyquinazoline (410 mg, 1.19 mmol) in Propan-2-ol (60 mL) was added TsOH. H ₂O (68 mg, 0.36 mmol) and 4- ( [1, 2, 4] triazolo [1, 5-c] pyrimidin-7-yloxy) -3-methylaniline (259 mg, 1.07 mmol) . The resulting mixture was stirred at 100℃ under Ar ₂protection and concentrated. The residue was dissolved in H ₂O (100 mL) , basified with aq. NaHCO ₃to pH =7-8, extracted with DCM: MeOH = 20: 1 (100 mLx3) . The combined organic layers were dried over anhydrous Na ₂SO ₄, filtered and concentrated. The residue was purified by column chromatography (DCM/MeOH=30/1) to give product (300 mg, 46%yield) as white solid. The racemic material was subsequently separated by chiral SFC to give two isomers:

[0699]

(R) -N- (4- ( [1, 2, 4] triazolo [1, 5-c] pyrimidin-7-yloxy) -3-methylphenyl) -5- ( (3, 3-difluoro-1-methylpiperidin-4-yl) oxy) -6-methoxyquinazolin-4-amine (Peak 1, retention time 6.241 min, ee: >99%) (100 mg, 67%) as a white solid. MS (ESI) m/z: 549.2 (M+H) ⁺. ¹H NMR (400 MHz, CDCl ₃) δ 10.04 (s, 1H) , 9.20 (s, 1H) , 8.61 (s, 1H) , 8.33 (s, 1H) , 7.88 (d, J = 2.0 Hz, 1H) , 7.79-7.76 (m, 1H) 7.69 (d, J = 9.2 Hz, 1H) , 7.53 (d, J = 9.2 Hz, 1H) , 7.11 (d, J = 8.8 Hz, 1H) , 6.90 (s, 1H) , 4.84-4.79 (m, 1H) , 4.03 (s, 3H) , 3.22-3.21 (m, 1H) , 2.93 (d, J = 7.2 Hz, 1H) , 2.38 (s, 3H) , 2.41-2.34 (m, 1H) , 2.34-2.27 (m, 1H) , 2.19 (s, 3H) , 2.16-2.10 (m, 2H) .

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References

• Quinazoline derivatives as antitumor agentsPublication Number:US-2023293533-A1Priority Date:2018-09-18
• Quinazoline derivatives as antitumor agentsPublication Number:ES-2971927-T3Priority Date:2018-09-18Grant Date:2024-06-10
• Quinazoline derivatives as antitumor agentsPublication Number:EP-4360713-B1Priority Date:2018-09-18Grant Date:2024-10-30
• Quinazoline derivatives as antitumor agentsPublication Number:ES-3007082-T3Priority Date:2018-09-18Grant Date:2025-03-19
• Quinazoline derivatives as antitumor agentsPublication Number:EP-4360713-A2Priority Date:2018-09-18
• Quinazoline derivatives as antitumor agentsPublication Number:EP-3853220-B1Priority Date:2018-09-18Grant Date:2024-01-03
• Quinazoline derivatives as antitumor agentsPublication Number:EP-3853220-A1Priority Date:2018-09-18
• Quinazoline derivatives as antitumor agentsPublication Number:US-2021386742-A1Priority Date:2018-09-18
• Quinazoline derivatives as antitumor agentsPublication Number:US-11723908-B2Priority Date:2018-09-18Grant Date:2023-08-15
• Crystalline forms of quinazoline derivatives, preparation, compositions and uses thereofPublication Number:CN-120623183-APriority Date:2021-10-20
• Crystalline forms of quinazoline derivatives, preparation, compositions and uses thereofPublication Number:CN-120309621-APriority Date:2021-10-20
• Quinazoline derivatives as antitumor agentsPublication Number:WO-2020057511-A1Priority Date:2018-09-18
• Quinazoline Derivatives as Antitumor AgentsPublication Number:JP-7546550-B2Priority Date:2018-09-18Grant Date:2024-09-06
• Quinazoline derivatives as antitumor agentsPublication Number:CA-3099776-A1Priority Date:2018-09-18

/////////perzebertinib, anax labs, epidermal growth factor receptor tyrosine kinase inhibitor, antineoplastic, ZN-A-1041, ZN 1041, RG 6596, Bizrolertinib, UN8TM5120C

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Petadeferitrin

 

Petadeferitrin

CAS911714-45-9

MFC16H21NO6S MW355.4 g/mol

(4S)-2-[2-hydroxy-4-[2-(2-methoxyethoxy)ethoxy]phenyl]-4-methyl-5H-1,3-thiazole-4-carboxylic acid

• (4S)-4,5-Dihydro-2-(2-hydroxy-4-(2-(2-methoxyethoxy)ethoxy)phenyl)-4-methyl-4-thiazolecarboxylic acid
• 4-Thiazolecarboxylic acid, 4,5-dihydro-2-(2-hydroxy-4-(2-(2-methoxyethoxy)ethoxy)phenyl)-4-methyl-, (4S)-
• (4S)-4,5-dihydro-2-[2-hydroxy-4-[2-(2-methoxyethoxy)ethoxy]phenyl]-4-methyl-4-thiazolecarboxylic acid

(4S)-2-{2-hydroxy-4-[2-(2-methoxyethoxy)ethoxy]phenyl}-4-methyl4,5-dihydro-1,3-thiazole-4-carboxylic acid
iron chelating agent, SP 420, WBX54NZ436

Petadeferitrin is an orally bioavailable iron-chelating agent and derivative of desferrithiocin, with iron chelating and protective activities in diseases of iron overload. Upon oral administration, petadeferitrin targets, binds to and chelates free iron. This induces the excretion of iron, prevents iron accumulation and prevents cellular and/or tissue damage associated with iron overload.

Petadeferitrin (formerly known as SP-420) is an investigational, orally bioavailable, small-molecule iron chelator being developed by Pharmacosmos (and its subsidiary Abfero Pharmaceuticals) to treat patients with transfusion-dependent iron overload. The drug works by binding to excess free iron in the body and forming complexes that are primarily excreted through bile and feces.

Key Characteristics & Mechanisms

• Drug Class: It is a tridentate iron chelator and a derivative of desferrithiocin.
• Enhanced Efficiency: In preclinical studies, it demonstrated a higher iron clearance efficiency (ICE value of 26.7) compared to desferrithiocin.
• Brain-Penetrant: It is uniquely characterized as a brain-penetrant agent, which could expand its potential protective use in specific diseases associated with iron accumulation.

Clinical Development Status

• Investigational Status: The drug remains investigational and has not yet been approved for commercial use anywhere in the world.
• Target Diseases: Clinical evaluation focuses on individuals who suffer from iron overload due to frequent blood transfusions, such as patients with β-thalassemia and sickle cell disease.
• Ongoing Studies: Pharmacosmos is actively evaluating the drug in Phase II clinical trials (such as ClinicalTrials.gov ID NCT05693909) to assess its safety, tolerability, and dosing advantages over existing options. Early human data suggests it may offer effective clearance with less frequent dosing compared to some currently approved alternatives.

• A Trial Testing SP-420 in Subjects With Transfusion-dependent β-thalassemia or Low-risk Myelodysplastic SyndromesCTID:NCT05693909Phase:Phase 2Status:RecruitingDate:2025-09-24
• Safety of SP-420 in the Treatment of Transfusional Iron OverloadCTID:NCT04741542Phase:Phase 1Status:TerminatedDate:2024-12-27
• SP-420 in Subjects With Transfusion-dependent Beta-Thalassemia or Other Rare AnemiasCTID:NCT03801889Phase:Phase 2Status:WithdrawnDate:2020-10-05
• Safety and Pharmacokinetic Study of Escalating Doses of SP-420, an Iron Chelator, in Patients With β-ThalassemiaCTID:NCT02274233Phase:Phase 1Status:TerminatedDate:2015-09-29

An open-label, dose-escalation, dose-finding, and proof-of-concept trial of SP-420 in subjects with transfusion-dependent β-thalassemiaEudraCT:2022-002395-36

Phase:Phase 2, Status:Trial now transitioned, Date:2022-12-16

SYN

https://patentscope.wipo.int/search/en/detail.jsf?docId=US42268401&_cid=P21-MSCM3W-69668-1

SYN

https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2006107626&_cid=P21-MSCM3W-69668-1

PAT

https://patentscope.wipo.int/search/en/detail.jsf?docId=US43268075&_cid=P21-MSCM3W-69668-1

PAT

Desferrithiocin polyether analoguesPublication Number:

US-2017217912-A1Priority Date:

2005-04-04

• Deferithiocin polyether analoguePublication Number:JP-6178816-B2Priority Date:2005-04-04Grant Date:2017-08-09
• Deferithiocin polyether analoguePublication Number:JP-2008536833-APriority Date:2005-04-04
• Desferrithiocin polyether analoguesPublication Number:EP-3190106-A1Priority Date:2005-04-04
• Desferrithiocin polyether analoguesPublication Number:US-9567309-B2Priority Date:2005-04-04Grant Date:2017-02-14
• Desferrithiocin polyether analoguesPublication Number:US-2013030028-A1Priority Date:2005-04-04

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References

• Target Class Profiling of Small-Molecule MethyltransferasesPublication Name:ACS Chemical BiologyPublication Date:2023-03-28PMCID:PMC10983791PMID:36976909DOI:10.1021/acschembio.3c00124
• Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitorsPublication Name:Proceedings of the National Academy of Sciences of the United States of AmericaPublication Date:2020-11-23PMCID:PMC7733812PMID:33229545DOI:10.1073/pnas.2005463117
• Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput ScreeningPublication Name:SLAS discovery : advancing life sciences R & DPublication Date:2020-01PMCID:PMC10791069PMID:31498718DOI:10.1177/2472555219873068
• A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoproteinPublication Name:Molecular PharmacologyPublication Date:2019-11PMCID:PMC6790066PMID:31515284DOI:10.1124/mol.119.115964
• Safety and pharmacokinetics of the oral iron chelator SP‐420 in β‐thalassemiaPublication Name:American Journal of HematologyPublication Date:2017-10-31PMID:28940308DOI:10.1002/ajh.24914
• Metabolically programmed iron chelatorsPublication Name:Bioorganic & Medicinal ChemistryPublication Date:2015-09-01PMCID:PMC4608554PMID:26231739DOI:10.1016/j.bmc.2015.06.059
• Substituent Effects on Desferrithiocin and Desferrithiocin Analogue Iron-Clearing and Toxicity ProfilesPublication Name:Journal of Medicinal ChemistryPublication Date:2012-08-13PMCID:PMC3583384PMID:22889170DOI:10.1021/jm300509y
• CCDC 757291: Experimental Crystal Structure DeterminationPublication Date:2011DOI:10.5517/cctf0rz
• The Impact of Polyether Chain Length on the Iron Clearing Efficiency and Physiochemical Properties of Desferrithiocin AnaloguesPublication Name:Journal of Medicinal ChemistryPublication Date:2010-04-08PMCID:PMC2951135PMID:20232803DOI:10.1021/jm9018146

/////////petadeferitrin, ANAX LABS, iron chelating agent, SP 420, WBX54NZ436

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Peturadol

 

Peturadol

CAS 686301-48-4

MFC12H20N6O MW264.33 g/mol

• 5-[2-(6-aminopurin-9-yl)ethylamino]pentan-1-ol
• 5-{[2-(6-amino-9H-purin-9-yl)ethyl]amino}pentan-1-ol

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 Number	Sponsor	Condition	Start Date	Phase
NCT01324466	NanoBio Corporation	Recurrent Herpes Labialis	2011-04	PHASE3
NCT05290493	Nobias Therapeutics, Inc.	22q11 Deletion Syndrome	2022-02-10	PHASE2
NCT01695187	NanoBio Corporation	Herpes Labialis	2012-10	PHASE3
NCT01321359	NanoBio Corporation	Recurrent Herpes Simplex Labialis	2011-04	PHASE3
NCT00453401	NanoBio Corporation	Herpes Labialis	2007-02	PHASE2

• 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

• Method for treating neuronal and non-neuronal painPublication Number:CA-2625553-CPriority Date:2005-10-14Grant Date:2014-03-11
• Method for treating neuronal and non-neuronal painPublication Number:WO-2007041863-A1Priority Date:2005-10-14
• Methods for treating herpes virus infectionsPublication Number:CA-2721510-A1Priority Date:2008-04-18
• Method for treating neuronal and non-neuronal painPublication Number:EP-1948182-B1Priority Date:2005-10-14Grant Date:2012-12-12
• Method for Treating Neuronal and Non-Neuronal PainPublication Number:US-2009233922-A1Priority Date:2005-10-14
• Method for treating neuronal and non-neuronal painPublication Number:CA-2625553-A1Priority Date:2005-10-14
• Methods for treating neural and non-neuralgiaPublication Number:JP-5404045-B2Priority Date:2005-10-14Grant Date:2014-01-29
• Neuronal stem cell differentiationPublication Number:WO-2015055987-A1Priority Date:2013-10-14
• Phosphodiesterase Inhibitor TreatmentPublication Number:US-2024108627-A1Priority Date:2013-03-15
• Phosphodiesterase Inhibitor TreatmentPublication Number:US-2022226332-A1Priority Date:2013-03-15
• Process for preparing an enantiomerically enriched, deuterated secondary alcohol from a corresponding ketone without reducing deuterium incorporationPublication Number:US-9074233-B2Priority Date:2010-09-01Grant Date:2015-07-07
• Methods for treating herpes virus infectionsPublication Number:US-2010075914-A1Priority Date:2008-04-18
• Anti-hsv pre-exposure prophylaxisPublication Number:EP-3166680-B1Priority Date:2014-07-07Grant Date:2023-11-15
• Viral prophylaxis treatment methods and pre-exposure prophylaxis kitsPublication Number:EP-4342545-A2Priority Date:2014-07-07
• Neuronal stem cell differentiationPublication Number:EP-3058064-A1Priority Date:2013-10-14
• neuronal stem cell differentiationPublication Number:CN-105658787-APriority Date:2013-10-14
• Neuronal stem cell differentiationPublication Number:US-2016257930-A1Priority Date:2013-10-14

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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

Peturadol

 

Peturadol

CAS 686301-48-4

MFC12H20N6O MW264.33 g/mol

• 5-[2-(6-aminopurin-9-yl)ethylamino]pentan-1-ol
• 5-{[2-(6-amino-9H-purin-9-yl)ethyl]amino}pentan-1-ol

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 Number	Sponsor	Condition	Start Date	Phase
NCT01324466	NanoBio Corporation	Recurrent Herpes Labialis	2011-04	PHASE3
NCT05290493	Nobias Therapeutics, Inc.	22q11 Deletion Syndrome	2022-02-10	PHASE2
NCT01695187	NanoBio Corporation	Herpes Labialis	2012-10	PHASE3
NCT01321359	NanoBio Corporation	Recurrent Herpes Simplex Labialis	2011-04	PHASE3
NCT00453401	NanoBio Corporation	Herpes Labialis	2007-02	PHASE2

• 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

• Method for treating neuronal and non-neuronal painPublication Number:CA-2625553-CPriority Date:2005-10-14Grant Date:2014-03-11
• Method for treating neuronal and non-neuronal painPublication Number:WO-2007041863-A1Priority Date:2005-10-14
• Methods for treating herpes virus infectionsPublication Number:CA-2721510-A1Priority Date:2008-04-18
• Method for treating neuronal and non-neuronal painPublication Number:EP-1948182-B1Priority Date:2005-10-14Grant Date:2012-12-12
• Method for Treating Neuronal and Non-Neuronal PainPublication Number:US-2009233922-A1Priority Date:2005-10-14
• Method for treating neuronal and non-neuronal painPublication Number:CA-2625553-A1Priority Date:2005-10-14
• Methods for treating neural and non-neuralgiaPublication Number:JP-5404045-B2Priority Date:2005-10-14Grant Date:2014-01-29
• Neuronal stem cell differentiationPublication Number:WO-2015055987-A1Priority Date:2013-10-14
• Phosphodiesterase Inhibitor TreatmentPublication Number:US-2024108627-A1Priority Date:2013-03-15
• Phosphodiesterase Inhibitor TreatmentPublication Number:US-2022226332-A1Priority Date:2013-03-15
• Process for preparing an enantiomerically enriched, deuterated secondary alcohol from a corresponding ketone without reducing deuterium incorporationPublication Number:US-9074233-B2Priority Date:2010-09-01Grant Date:2015-07-07
• Methods for treating herpes virus infectionsPublication Number:US-2010075914-A1Priority Date:2008-04-18
• Anti-hsv pre-exposure prophylaxisPublication Number:EP-3166680-B1Priority Date:2014-07-07Grant Date:2023-11-15
• Viral prophylaxis treatment methods and pre-exposure prophylaxis kitsPublication Number:EP-4342545-A2Priority Date:2014-07-07
• Neuronal stem cell differentiationPublication Number:EP-3058064-A1Priority Date:2013-10-14
• neuronal stem cell differentiationPublication Number:CN-105658787-APriority Date:2013-10-14
• Neuronal stem cell differentiationPublication Number:US-2016257930-A1Priority Date:2013-10-14

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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

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.

• US11339167,

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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Phone : +91 897704 2010 /  +91 9177075735, Email : info@anaxlab.com

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References

• Tartrate salt 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, crystalline form thereof, and method for preparing samePublication Number:WO-2025121903-A1Priority Date:2023-12-05
• Method for 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, and intermediate compounds thereofPublication Number:WO-2025121899-A1Priority Date:2023-12-05
• Phosphate salt 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, crystalline form thereof, and method for preparation thereofPublication Number:WO-2025121900-A1Priority Date:2023-12-05
• Oxy-fluoropiperidine derivative as kinase inhibitorPublication Number:EP-3733673-A1Priority Date:2017-12-28
• Oxy-fluoropiperidine Derivative as Kinase InhibitorPublication Number:US-2020308177-A1Priority Date:2017-12-28
• Oxy-fluoropiperidine compounds as kinase inhibitors, pharmaceutical composition comprising the same and their use in the prevention or treatment of inflammatory diseases, autoimmune diseases, proliferative diseases or hyperproliferative diseases and immune-mediated diseases, cancers, tumorsPublication Number:BR-112020013141-B1Priority Date:2017-12-28
• Substituted piperidines as kinase inhibitorsPublication Number:US-11339167-B2Priority Date:2017-12-28Grant Date:2022-05-24
• Oxy-haloperidine derivatives as kinase inhibitorsPublication Number:CN-111527091-APriority Date:2017-12-28
• Oxy-fluoropiperidine derivatives as kinase inhibitorPublication Number:KR-102318929-B1Priority Date:2017-12-28Grant Date:2021-10-28
• Oxy-fluoropiperidine derivative as a kinase inhibitorPublication Number:JP-6995428-B2Priority Date:2017-12-28Grant Date:2022-01-14
• Oxy-fluoropiperidine derivatives as kinase inhibitorPublication Number:CA-3084962-A1Priority Date:2017-12-28
• Oxy-fluoropiperidine derivative as a kinase inhibitorPublication Number:ES-2922633-T3Priority Date:2017-12-28Grant Date:2022-09-19
• Oxy-fluoropiperidine derivatives as kinase inhibitorPublication Number:KR-20190080803-APriority Date:2017-12-28
• Oxy-fluoropiperidine derivatives as kinase inhibitorPublication Number:CA-3084962-CPriority Date:2017-12-28Grant Date:2022-08-09
• Oxy-fluoropiperidine derivative as kinase inhibitorPublication Number:EP-3733673-B1Priority Date:2017-12-28Grant Date:2022-06-29
• Oxy-haloperidine derivatives as kinase inhibitorsPublication Number:CN-111527091-BPriority Date:2017-12-28Grant Date:2023-03-28
• Oxy-fluoropiperidine derivatives as kinase inhibitorPublication Number:KR-20210062618-APriority Date:2017-12-28
• Oxy-fluoropiperidine derivatives as kinase inhibitorPublication Number:KR-102592083-B1Priority Date:2017-12-28Grant Date:2023-10-20
• OXY-FLUOROPIPERIDINE DERIVATIVE AS A KINASE INHIBITORPublication Number:HR-P20221043-T1Priority Date:2017-12-28
• Oxy-fluoropiperidine derivative as kinase inhibitorPublication Number:IL-275207-BPriority Date:2017-12-28

/////////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