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