1141473-84-8

Basic information

• Product Name: methyl 4-bromo-3-(methoxymethyl)benzoate
• Synonyms: methyl 4-bromo-3-(methoxymethyl)benzoate
• CAS NO: 1141473-84-8
• Molecular Formula: C₁₀H₁₁BrO₃
• Molecular Weight: 259.09654
• Mol File: 1141473-84-8.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: methyl 4-bromo-3-(methoxymethyl)benzoate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 4-bromo-3-(methoxymethyl)benzoate(1141473-84-8)
• EPA Substance Registry System: methyl 4-bromo-3-(methoxymethyl)benzoate(1141473-84-8)

Safety Data

• Hazardous Substances Data: 1141473-84-8(Hazardous Substances Data)

Upstream product

• 148547-19-7 4-Bromo-3-methylbenzoic acid methyl ester 
• 67-56-1 methanol 
• 142031-67-2 methyl 4-bromo-3-(bromomethyl)benzoate 

Downstream Products

• 1243560-58-8 methyl (2S,4R)-1-(3-chloro-5-(5-(2-(methoxymethyl)-2'-methylbiphenyl-4-yl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)-4-(tert-butyldimethylsilyloxy)-pyrrolidine-2-carboxylate 
• 1243560-59-9 methyl (2S,4R)-1-(3-chloro-5-(5-(2-(methoxymethyl)-2'-methylbiphenyl-4-yl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)-4-hydroxypyrrolidine-2-carboxylate 
• 1243558-87-3 (2S,4R)-1-(3-chloro-5-(5-(2-(methoxymethyl)-2'-methylbiphenyl-4-yl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)-4-hydroxypyrrolidine-2-carboxylic acid 
• 1243558-88-4 (2R,4R)-1-(3-chloro-5-(5-(2-(methoxymethyl)-2'-methylbiphenyl-4-yl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)-4-hydroxypyrrolidine-2-carboxylic acid 
• 107317-58-8 4-bromo-3-trifluoromethylbenzoic acid methyl ester 
• 1141473-18-8 N-(2-fluoro-5-{5-[2-(methoxymethyl)-2’-methylbiphenyl-4-yl]-1,2,4-oxadiazol-3-yl}benzyl)-N-methylglycine hydrochloride 
• 1246527-59-2 tert-butyl N-(4-{5-[2-(methoxymethyl)-2'-(trifluoromethyl)biphenyl-4-yl]-1,2,4-oxadiazol-3-yl}benzyl)-N-methylglycinate 

Relevant articles and documents

Pharmacophore-based design of novel oxadiazoles as selective sphingosine-1-phosphate (S1P) receptor agonists with in vivo efficacy

Sphingosine-1-phosphate (S1P) receptor agonists have shown promise as therapeutic agents for multiple sclerosis (MS) due to their regulatory roles within the immune, central nervous system, and cardiovascular system. Here, the design and optimization of novel [1,2,4]oxadiazole derivatives as selective S1P receptor agonists are described. The structure-activity relationship exploration was carried out on the three dominant segments of the series: modification of the polar head group (P), replacement of the oxadiazole linker (L) with different five-membered heterocycles, and the use of diverse 2,2′-disubstituted biphenyl moieties as the hydrophobic tail (H). All three segments have a significant impact on potency, S1P receptor subtype selectivity, physicochemical properties, and in vitro absorption, distribution, metabolism, excretion and toxicity (ADMET) profile of the compounds. From these optimization studies, a selective S1P1 agonist, N-methyl-N-(4-{5-[2-methyl-2′-(trifluoromethyl)biphenyl-4-yl]-1,2,4-oxadiazol-3-yl}benzyl)glycine (45), and a dual S1P1,5 agonist, N-methyl-N-(3-{5-[2′-methyl-2-(trifluoromethyl)biphenyl-4-yl]-1,2,4-oxadiazol-3-yl}benzyl)glycine (49), emerged as frontrunners. These compounds distribute predominantly in lymph nodes and brain over plasma and induce long lasting decreases in lymphocyte count after oral administration. When evaluated head-to-head in an experimental autoimmune encephalomyelitis mouse model, together with the marketed drug fingolimod, a pan-S1P receptor agonist, S1P1,5 agonist 49 demonstrated comparable efficacy while S1P1-selective agonist 45 was less potent. Compound 49 is not a prodrug, and its improved property profile should translate into a safer treatment of relapsing forms of MS.

5-(BIPHENYL-4-YL)-3-PHENYL-1,2,4-OXADIAZOLYL DERIVATIVES AS LIGANDS ON THE SPHINGOSINE 1-PHOSPHATE (S1P) RECEPTORS

The present invention provides compounds of Formula (I), as selective S1 P1 inhibitors, as well as their use for treating multiple sclerosis and other diseases.

OXADIAZOLE FUSED HETEROCYCLIC DERIVATIVES USEFUL FOR THE TREATMENT OF MULTIPLE SCLEROSIS

The invention provides compounds of Formula (I) for the treatment of multiple sclerosis and other diseases.

OXAZOLE PYRIDINE DERIVATIVES USEFUL AS S1P1 RECEPTOR AGONISTS

The present invention provides oxadiazole pyridine derivatives of Formula (I), their use as medicaments and their use for treating multiple sclerosis and other diseases

4,4-DISUBSTITUTED PIPERIDINES

The application relates to 4,4-disubstituted piperidines of the general formula (I) and their salts, preferably their pharmaceutically acceptable salts, in which R2, has the meanings explained in the description, a process for their preparation

OXADIAZOLE DERIVATIVES

The invention relates to compounds of formula (I): wherein R1, R2, Ra, Rb, W, Q and S have the meanings given in claim 1. The compounds are useful e.g. in the treatment of autoimmune disorders, such as multiple sclerosis.