187401-45-2

Basic information

• Product Name: 3-Pyridinecarboxylic acid, 5-chloro-6-(1-methylethoxy)-
• Synonyms: 3-Pyridinecarboxylic acid, 5-chloro-6-(1-methylethoxy)-;5-chloro-6-isopropoxynicotinic acid
• CAS NO: 187401-45-2
• Molecular Formula: C₉H₁₀ClNO₃
• Molecular Weight: 215.635
• Mol File: 187401-45-2.mol

Chemical Properties

• Boiling Point: 314.9±37.0 °C(Predicted)
• Appearance: /
• Density: 1.310±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 3.55±0.10(Predicted)
• CAS DataBase Reference: 3-Pyridinecarboxylic acid, 5-chloro-6-(1-methylethoxy)-(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Pyridinecarboxylic acid, 5-chloro-6-(1-methylethoxy)-(187401-45-2)
• EPA Substance Registry System: 3-Pyridinecarboxylic acid, 5-chloro-6-(1-methylethoxy)-(187401-45-2)

Safety Data

• Hazardous Substances Data: 187401-45-2(Hazardous Substances Data)

Usage

Uses

Used in Research and Industrial Sector:
3-Pyridinecarboxylic acid, 5-chloro-6-(1-methylethoxy)-, is used as a specialty chemical for its unique reactivity and stability. Its complex molecular structure allows it to be employed in various chemical reactions and processes, contributing to the development of new compounds and materials.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 3-Pyridinecarboxylic acid, 5-chloro-6-(1-methylethoxy)-, is used as an intermediate in the synthesis of various drugs and pharmaceutical compounds. Its unique functional groups and reactivity enable the creation of novel drug molecules with potential therapeutic applications.
Used in Agrochemical Industry:
3-Pyridinecarboxylic acid, 5-chloro-6-(1-methylethoxy)-, is also utilized in the agrochemical industry as a building block for the development of new pesticides and agrochemicals. Its chemical properties allow for the design of innovative compounds with improved efficacy and selectivity in crop protection.
Used in Material Science:
In the field of material science, 3-Pyridinecarboxylic acid, 5-chloro-6-(1-methylethoxy)-, is employed in the synthesis of advanced materials with specific properties. Its unique molecular structure can be incorporated into polymers, coatings, and other materials to enhance their performance and functionality.

Upstream product

• 54127-63-8 5-chloro-6-hydroxy-3-pyridinecarboxylic acid 
• 187401-46-3 1-methylethyl 5-chloro-6-[(1-methylethyl)oxy]-3-pyridinecarboxylate 
• 41667-95-2 5,6-dichloronicotinic acid 
• 67-63-0 isopropyl alcohol 

Downstream Products

• 1011476-57-5 5-chloro-6-isopropoxy-nicotinic acid (4-allyloxy-N-hydroxy-3,5-dimethyl-benzamidine) ester 
• 1011476-58-6 3-[3-(4-allyloxy-3,5-dimethyl-phenyl)-[1,2,4]oxadiazol-5-yl]-5-chloro-6-isopropoxy-pyridine 
• 1398512-07-6 C₂₄H₂₉ClN₄O₅ 
• 1246389-12-7 tert-butyl 4-((5-chloro-4-(2-(5-chloro-6-isopropoxynicotinoyl)hydrazinecarbonyl)-2-fluorophenoxy)methyl)-2,2-dimethyloxazolidine-3-carboxylate 
• 1259032-15-9 ethyl 4-{7-[(Z)-{[({5-chloro-6-[(1-methylethyl)oxy]-3-pyridinyl}carbonyl)oxy]imino}(amino)methyl]-1-[(4-methylphenyl)sulfonyl]-1H-indol-4-yl}butanoate 
• 1258959-73-7 ethyl 4-{7-[{[({3-chloro-4-[(1-methylethyl)oxy]phenyl}carbonyl)oxy]amino}(imino)methyl]-1-[(4-methylphenyl)sulfonyl]-1H-indol-4-yl}butanoate 
• 1258959-66-8 C₃₀H₃₁ClN₄O₇S 
• 1311202-93-3 tert butyl trans-3-[3-chloro-4-{5-(5-chloro-6-isopropoxypyridin-3-yl)-1,2,4-oxadiazol-3-yl}phenoxy]cyclobutanecarboxylate 
• 1398512-07-6 C₂₄H₂₉ClN₄O₅ 
• 1260021-72-4 5-[3-(3-bromo-2-ethylphenyl)-1,2,4-oxadiazol-5-yl]-3-chloro-2-[(1-methylethyl)oxy]pyridine 
• 1260021-61-1 5-[3-(3-bromo-2-chlorophenyl)-1,2,4-oxadiazol-5-yl]-3-chloro-2-[(1-methylethyl)oxy]pyridine 
• 1260021-48-4 5-[3-(3-bromo-2-methylphenyl)-1,2,4-oxadiazol-5-yl]-3-chloro-2-[(1-methylethyl)oxy]pyridine 
• 1260022-53-4 5-{3-[3-bromo-5-fluoro-2-(methyloxy)phenyl]-1,2,4-oxadiazol-5-yl}-3-chloro-2-[(1-methylethyl)oxy]pyridine 

Relevant articles and documents

Optimization of sphingosine-1-phosphate-1 receptor agonists: Effects of acidic, basic, and zwitterionic chemotypes on pharmacokinetic and pharmacodynamic profiles

The efficacy of the recently approved drug fingolimod (FTY720) in multiple sclerosis patients results from the action of its phosphate metabolite on sphingosine-1-phosphate S1P1 receptors, while a variety of side effects have been ascribed to its S1P3 receptor activity. Although S1P and phospho-fingolimod share the same structural elements of a zwitterionic headgroup and lipophilic tail, a variety of chemotypes have been found to show S1P1 receptor agonism. Here we describe a study of the tolerance of the S1P1 and S1P3 receptors toward bicyclic heterocycles of systematically varied shape and connectivity incorporating acidic, basic, or zwitterionic headgroups. We compare their physicochemical properties, their performance in in vitro and in vivo pharmacokinetic models, and their efficacy in peripheral lymphocyte lowering. The campaign resulted in the identification of several potent S1P1 receptor agonists with good selectivity vs S1P3 receptors, efficacy at 1 mg/kg oral doses, and developability properties suitable for progression into preclinical development.

OXADIAZOLE SUBSTITUTED INDAZOLE DERIVATIVES FOR USE AS SPHINGOSINE 1-PHOSPHATE 1 (S1P1) RECEPTOR AGONISTS

Oxadiazole substituted indazole derivatives of formula (I) or pharmaceutical salts thereof having pharmacological activity, processes for their preparation, pharmaceutical compositions containing them and their uses in the treatment of various disorders mediated by S1P1 receptors are disclosed.

Discovery of a selective S1P1 receptor agonist efficacious at low oral dose and devoid of effects on heart rate

Gilenya (fingolimod, FTY720) was recently approved by the U.S. FDA for the treatment of patients with remitting relapsing multiple sclerosis (RRMS). It is a potent agonist of four of the five sphingosine 1-phosphate (S1P) G-protein-coupled receptors (S1P1 and S1P3-5). It has been postulated that fingolimod's efficacy is due to S1P1 agonism, while its cardiovascular side effects (transient bradycardia and hypertension) are due to S1P3 agonism. We have discovered a series of selective S1P 1 agonists, which includes 3-[6-(5-{3-cyano-4-[(1-methylethyl)oxy] phenyl}-1,2,4-oxadiazol-3-yl)-5-methyl-3,4-dihydro-2(1H)-isoquinolinyl] propanoate, 20, a potent, S1P3-sparing, orally active S1P1 agonist. Compound 20 is as efficacious as fingolimod in a collagen-induced arthritis model and shows excellent pharmacokinetic properties preclinically. Importantly, the selectivity of 20 against S1P3 is responsible for an absence of cardiovascular signal in telemetered rats, even at high dose levels.

OXADIAZOLE SUBSTITUTED INDAZOLE DERIVATIVES FOR USE AS SPHINGOSINE 1-PHOSPHATE 1 (S1P1) RECEPTOR AGONISTS

Oxadiazole substituted indazole derivatives of formula (I) or pharmaceutical salts thereof having pharmacological activity, processes for their preparation, pharmaceutical compositions containing them and their uses in the treatment of various disorders mediated by S1P1 receptor are disclosed.

Pyridin-3-yl derivatives as immunomodulating agents

The invention relates to pyridin-3-yl derivatives of Formula (I) wherein R1, R2, R3, R4, R5; R6 and A are as described in the description, their preparation and their use as pharmaceuticall

Modulators of S1P and Methods of Making And Using

The invention is directed to Compounds of Formula I: as well as methods of making and using the compounds.

OXADIAZOLE DERIVATIVES AS S1P1 RECEPTOR AGONISTS

The present invention relates to novel oxadiazole compounds of formula (I) having pharmacological activity, processes for their preparation, pharmaceutical compositions containing them and their use in the treatment of various disorders.

INDOLE DERIVATIVES AS S1P1 RECEPTOR AGONISTS

The invention relates to compounds of formula (I) wherein one of R5 and R6 is hydrogen or R2 and the other is (a) processes for their preparation, pharmaceutical compositions containing them and their use in the treatment

OXADIAZOLE SUBSTITUTED INDAZOLE DERIVATIVES FOR USE AS SPHINGOSINE 1-PHOSPHATE (S1P) AGONISTS

The present invention provides compounds of formula (I) or salts thereof, having pharmacological activity, processes for their preparation, pharmaceutical compositions containing them and their use in the treatment of various disorders mediated by S1P1 receptors.