VU6009453

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MedKoo CAT#: 563779

CAS#: 2148929-11-5

Description: VU6009453 is a novel M4 positive allosteric modulator (PAM). VU6009453 showed good potency (EC50=383 nM) and excellent CNS penetration (rat Kp=3.4, Kp,uu=0.84).


Price and Availability

Size Price Shipping out time Quantity
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Pricing updated 2020-10-25. Prices are subject to change without notice.

VU6009453 is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 563779
Name: VU6009453
CAS#: 2148929-11-5
Chemical Formula: C21H21ClN4O2
Exact Mass: 396.1353
Molecular Weight: 396.88
Elemental Analysis: C, 63.55; H, 5.33; Cl, 8.93; N, 14.12; O, 8.06


Synonym: VU6009453; VU 6009453; VU-6009453

IUPAC/Chemical Name: N-(1-(5-Chloro-2-methoxypyridin-4-yl)azetidin-3-yl)-2,4-dimethylquinoline-6-carboxamide

InChi Key: NVGMPSJSLKIVIT-UHFFFAOYSA-N

InChi Code: InChI=1S/C21H21ClN4O2/c1-12-6-13(2)24-18-5-4-14(7-16(12)18)21(27)25-15-10-26(11-15)19-8-20(28-3)23-9-17(19)22/h4-9,15H,10-11H2,1-3H3,(H,25,27)

SMILES Code: O=C(C1=CC=C2N=C(C)C=C(C)C2=C1)NC3CN(C4=CC(OC)=NC=C4Cl)C3


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO

Shelf Life:
>3 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code:
2934.99.03.00


References

1: Tarr JC, Wood MR, Noetzel MJ, Melancon BJ, Lamsal A, Luscombe VB, Rodriguez AL, Byers FW, Chang S, Cho HP, Engers DW, Jones CK, Niswender CM, Wood MW, Brandon NJ, Duggan ME, Jeffrey Conn P, Bridges TM, Lindsley CW. Corrigendum to "Challenges in the development of an M(4) PAM preclinical candidate: The discovery, SAR, and biological characterization of a series of azetidine-derived tertiary amides" [Bioorg. Med. Chem. Lett. 27(23) (2017) 5179-5184]. Bioorg Med Chem Lett. 2018 Sep 15;28(17):3014. doi: 10.1016/j.bmcl.2018.07.022. Epub 2018 Jul 31. PubMed PMID: 30076050.

2: Tarr JC, Wood MR, Noetzel MJ, Melancon BJ, Lamsal A, Luscombe VB, Rodriguez AL, Byers FW, Chang S, Cho HP, Engers DW, Jones CK, Niswender CM, Wood MW, Brandon NJ, Duggan ME, Conn PJ, Bridges TM, Lindsley CW. Challenges in the development of an M(4) PAM preclinical candidate: The discovery, SAR, and biological characterization of a series of azetidine-derived tertiary amides. Bioorg Med Chem Lett. 2017 Dec 1;27(23):5179-5184. doi: 10.1016/j.bmcl.2017.10.053. Epub 2017 Oct 24. Erratum in: Bioorg Med Chem Lett. 2018 Sep 15;28(17):3014. PubMed PMID: 29089231.

3: Bewley BR, Spearing PK, Weiner RL, Luscombe VB, Zhan X, Chang S, Cho HP, Rodriguez AL, Niswender CM, Conn PJ, Bridges TM, Engers DW, Lindsley CW. Discovery of a novel, CNS penetrant M(4) PAM chemotype based on a 6-fluoro-4-(piperidin-1-yl)quinoline-3-carbonitrile core. Bioorg Med Chem Lett. 2017 Sep 15;27(18):4274-4279. doi: 10.1016/j.bmcl.2017.08.043. Epub 2017 Aug 20. PubMed PMID: 28866269; PubMed Central PMCID: PMC5688877.

4: Gould RW, Grannan MD, Gunter BW, Ball J, Bubser M, Bridges TM, Wess J, Wood MW, Brandon NJ, Duggan ME, Niswender CM, Lindsley CW, Conn PJ, Jones CK. Cognitive enhancement and antipsychotic-like activity following repeated dosing with the selective M(4) PAM VU0467154. Neuropharmacology. 2018 Jan;128:492-502. doi: 10.1016/j.neuropharm.2017.07.013. Epub 2017 Jul 17. PubMed PMID: 28729220.

5: Tarr JC, Wood MR, Noetzel MJ, Bertron JL, Weiner RL, Rodriguez AL, Lamsal A, Byers FW, Chang S, Cho HP, Jones CK, Niswender CM, Wood MW, Brandon NJ, Duggan ME, Conn PJ, Bridges TM, Lindsley CW. Challenges in the development of an M(4) PAM preclinical candidate: The discovery, SAR, and in vivo characterization of a series of 3-aminoazetidine-derived amides. Bioorg Med Chem Lett. 2017 Jul 1;27(13):2990-2995. doi: 10.1016/j.bmcl.2017.05.014. Epub 2017 May 6. PubMed PMID: 28522253; PubMed Central PMCID: PMC5518475.

6: Wood MR, Noetzel MJ, Melancon BJ, Poslusney MS, Nance KD, Hurtado MA, Luscombe VB, Weiner RL, Rodriguez AL, Lamsal A, Chang S, Bubser M, Blobaum AL, Engers DW, Niswender CM, Jones CK, Brandon NJ, Wood MW, Duggan ME, Conn PJ, Bridges TM, Lindsley CW. Discovery of VU0467485/AZ13713945: An M(4) PAM Evaluated as a Preclinical Candidate for the Treatment of Schizophrenia. ACS Med Chem Lett. 2016 Dec 16;8(2):233-238. doi: 10.1021/acsmedchemlett.6b00461. eCollection 2017 Feb 9. PubMed PMID: 28197318; PubMed Central PMCID: PMC5304297.

7: Wood MR, Noetzel MJ, Poslusney MS, Melancon BJ, Tarr JC, Lamsal A, Chang S, Luscombe VB, Weiner RL, Cho HP, Bubser M, Jones CK, Niswender CM, Wood MW, Engers DW, Brandon NJ, Duggan ME, Conn PJ, Bridges TM, Lindsley CW. Challenges in the development of an M(4) PAM in vivo tool compound: The discovery of VU0467154 and unexpected DMPK profiles of close analogs. Bioorg Med Chem Lett. 2017 Jan 15;27(2):171-175. doi: 10.1016/j.bmcl.2016.11.086. Epub 2016 Nov 30. PubMed PMID: 27939174; PubMed Central PMCID: PMC5340297.

8: Gould RW, Nedelcovych MT, Gong X, Tsai E, Bubser M, Bridges TM, Wood MR, Duggan ME, Brandon NJ, Dunlop J, Wood MW, Ivarsson M, Noetzel MJ, Daniels JS, Niswender CM, Lindsley CW, Conn PJ, Jones CK. State-dependent alterations in sleep/wake architecture elicited by the M4 PAM VU0467154 - Relation to antipsychotic-like drug effects. Neuropharmacology. 2016 Mar;102:244-53. doi: 10.1016/j.neuropharm.2015.11.016. Epub 2015 Nov 23. PubMed PMID: 26617071; PubMed Central PMCID: PMC4809053.

9: Niswender CM, Rodriguez AL, Sheffler DJ, Utley TJ, Vinson PN, Dawson ES, Jones CK, Wood MR, Daniels JS, Conn PJ, Engers JL, Le UM, Melancon BJ, Hopkins CR, Lindsley CW. Extended Probe Characterization: Development of an M(4) PAM with Improved Activity and Brain Exposure, while Avoiding Species Bias. 2011 Oct 31 [updated 2013 Mar 7]. Probe Reports from the NIH Molecular Libraries Program [Internet]. Bethesda (MD): National Center for Biotechnology Information (US); 2010-. Available from http://www.ncbi.nlm.nih.gov/books/NBK143536/ PubMed PMID: 23762942.