175965-65-8

Basic information

• Product Name: 8-METHOXY-[1,2,4]TRIAZOLO[1,5-A]PYRIDIN-2-AMINE
• Synonyms: 8-METHOXY-[1,2,4]TRIAZOLO[1,5-A]PYRIDIN-2-AMINE;8-Methoxy-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine;8-Methoxy-[1,2,4]triazol[1,5-a]pyridine-2-amine
• CAS NO: 175965-65-8
• Molecular Formula: C₇H₈N₄O
• Molecular Weight: 164.16
• Mol File: 175965-65-8.mol

Chemical Properties

• Appearance: /
• Density: 1.48
• Refractive Index: 1.701
• Storage Temp.: 2-8°C(protect from light)
• CAS DataBase Reference: 8-METHOXY-[1,2,4]TRIAZOLO[1,5-A]PYRIDIN-2-AMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 8-METHOXY-[1,2,4]TRIAZOLO[1,5-A]PYRIDIN-2-AMINE(175965-65-8)
• EPA Substance Registry System: 8-METHOXY-[1,2,4]TRIAZOLO[1,5-A]PYRIDIN-2-AMINE(175965-65-8)

Safety Data

• Hazardous Substances Data: 175965-65-8(Hazardous Substances Data)

Usage

Uses

Used in Medicinal Chemistry:
8-Methoxy-[1,2,4]triazolo[1,5-a]pyridin-2-amine is used as a chemical intermediate for the synthesis of various pharmaceutical compounds due to its unique structure and potential biological activities. Its presence in drug molecules may contribute to desired pharmacological properties, such as improved binding affinity, selectivity, and bioavailability.
Used in Drug Discovery:
In the pharmaceutical industry, 8-Methoxy-[1,2,4]triazolo[1,5-a]pyridin-2-amine is utilized as a lead compound in drug discovery programs. Its unique structural features make it a promising candidate for the development of new drugs targeting various therapeutic areas, including but not limited to oncology, infectious diseases, and neurological disorders.
Further research is necessary to elucidate the specific biological activities and mechanisms of action of 8-Methoxy-[1,2,4]triazolo[1,5-a]pyridin-2-amine, which will guide its optimization and application in drug development.

InChI:InChI=1/C7H8N4O/c1-12-5-3-2-4-11-6(5)9-7(8)10-11/h2-4H,1H3,(H2,8,10)

Upstream product

• 20265-37-6 3-methoxy-2-nitropyridine 
• 10201-71-5 3-methoxypyridin-2-amine 
• 16182-04-0 Ethoxycarbonyl isothiocyanate 
• 175965-58-9 ethyl N-[(3-methoxypyridin-2-yl)carbamothioyl]carbamate 

Downstream Products

• 1319067-40-7 2-bromo-8-methoxy-[1,2,4]triazolo[1,5-a]pyridine 
• 1319064-55-5 5-(8-Methoxy-[1,2,4]triazolo[1,5-a]pyridin-2-ylamino)-2-(4-methyl-imidazol-1-yl)-benzonitrile 
• 492468-97-0 8-methoxy-5-iodo-[1,2,4]triazolo[1,5-a]pyridin-2-yl-amine 
• 634195-36-1 8-methoxy-5-(4-methoxy-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine 
• 634195-42-9 8-methoxy-5-(3-trifluoromethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine 
• 685135-47-1 8-methoxy-5-o-tolyl-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine 
• 492468-98-1 8-methoxy-5-phenyl-[1,2,4]triazolo[1,5-a]pyridin-2-yl-amine 

Relevant articles and documents

Stepwise Design of γ-Secretase Modulators with an Advanced Profile by Judicious Coordinated Structural Replacements and an Unconventional Phenyl Ring Bioisostere

Starting from RO6800020 (1), our former γ-secretase modulator (GSM) lead compound, we utilized sequential structural replacements to improve the potency (IC50), pharmacokinetic properties including the free fraction (fraction unbound (fu)) in plasma, and in vivo efficacy. Importantly, we used novel CF3-alkoxy groups as bioisosteric replacements of a fluorinated phenyl ring and properties such as lipophilicity, solubility, metabolic stability, and free fraction could be balanced, maintaining low Pgp efflux needed for CNS penetration. In addition, by reducing aromaticity, we prevented phototoxicity. Additional substitution in the triazolopyridine core disturbed the binding to phosphatidylinositol 4-kinase, catalytic β (PIK4CB). We also introduced less lipophilic head heterocycles devoid of covalent binding (CVB) liability. After these changes, further modifications to the trifluoroethoxy bioisosteric replacement allowed rebalancing of properties, such as lipophilicity, and also potency. Our optimization strategy culminated with in vivo active RO7101556 (18B) having excellent properties and being selected as an advanced candidate.

BICYCLIC ETHER O-GLYCOPROTEIN-2-ACETAMIDO-2-DEOXY-3-D-GLUCOPYRANOSIDASE INHIBITORS

Described herein are compounds represented by formula (I) or a pharmaceutically acceptable salt thereof, pharmaceutical compositions comprising the same and methods of preparing and using the same. The variables Ar, X, R1, R3, R 4, Y1, Y2, n and p are as defined herein.

BRIDGED PIPERIDINE DERIVATIVES

The present invention relates to a compound of formula (I), wherein Het Ar is a five or six membered hetaryl group, containing one, two or three heteroatoms, selected from N, O or S; R1 is hydrogen, lower alkyl, lower alkyl substituted by halogen, halogen, or lower alkoxy; R2 is lower alkyl substituted by halogen, -CH2-C3-6-cycloalkyl, substituted by one or two substituents, selected from lower alkyl substituted by halogen or halogen, or is lower alkenyl substituted by halogen; R3 is hydrogen, lower alkyl substituted by halogen, lower alkyl, halogen, C3-6-cycloalkyl or lower alkyl substituted by hydroxy; n is 1 or 2; for n = 2, R1 can be independent to each other; Y is CH or N; or to a pharmaceutically active acid addition salt thereof, to a racemic mixture or its corresponding enantiomer and/or optical isomer and/or stereoisomer thereof. The compounds may be used for the treatment of Alzheimer's disease, cerebral amyloid angiopathy, hereditary cerebral hemorrhage with amyloidosis, Dutch-type (HCHWA-D), multi-infarct dementia, dementia pugilistica or Down syndrome.

Lead generation: Sowing the seeds for future success

Lead generation and the associated hit-to-lead process are key strategic elements in modern pharmaceutical research, and most companies have implemented this concept. Efficient lead generation is one of the main attempts to reduce the high attrition rates observed along the drug discovery process by focussing on the early developmental phases. The level of integration of the lead generation activities within the discovery organization, the flexibility in assessing and implementing new chemistries and new technologies, the high-quality standards set for the identification of the best possible chemical lead series will ultimately determine the future success in discovering new medicines.

Aromatic and heteroaromatic substituted 1,2,4-triazolo pyridine derivatives

The invention is a compound of formula or a pharmaceutically acceptable salt thereof, wherein R1and R2are as defined in the specification. A compound of formula I has a good affinity to the adenosine receptor and can therefore be used for the treatment or protection of diseases mediated by this receptor.

Synthetic access to 2-amido-5-aryl-8-methoxy-triazolopyridine and 2-amido-5-morpholino-8-methoxy-triazolopyridine derivatives as potential inhibitors of the adenosine receptor subtypes

Two versatile and complementary synthetic strategies towards 2-amido-5-aryl-8-methoxy-triazolopyridine derivatives and 2-amido-5-morpholino-8-methoxy-triazolopyridine derivatives in five steps are presented. The key step in each synthetic route can be constituted as the formation of the respective triazolopyridine derivative precursors in 78% and 57% yield, respectively, through an intermediately formed 4H-[1,2,4]oxadiazol-5-one. The final Suzuki coupling/amidation allowed the straightforward access to the desired triazolopyridine derivatives which have not been described previously. Notably, these triazolopyridine-scaffold bears three vectors of diversity which offer maximum flexibility in design and combinatorial synthesis of molecules with a potentially useful inhibitory activity towards adenosine receptor subtypes.