Ceralifimod

Base Information

• Chemical Name: Ceralifimod
• CAS No.: 891859-12-4
• Molecular Formula: C27H33NO4
• Molecular Weight: 435.563
• UNII: BZ2O8A84A4
• ChEMBL ID: CHEMBL4093489
• NCI Thesaurus Code: C171818
• Nikkaji Number: J3.268.960D
• Wikidata: Q27274973
• Mol file: 891859-12-4.mol

Synonyms:ceralifimod;ONO-4641

Chemical Property of Ceralifimod

Chemical Property:

• Boiling Point: 595.9±50.0 °C(Predicted)
• PKA: 2.71±0.20(Predicted)
• PSA: 59.00000
• Density: 1.172±0.06 g/cm3(Predicted)
• LogP: 4.90070
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 9
• Exact Mass: 435.24095853
• Heavy Atom Count: 32
• Complexity: 671

Purity/Quality:

99%+, ^*data from raw suppliers

Ceralifimod ≥95%(HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCC1=CC(=C(C=C1)COC2=CC3=C(C=C2)C(=C(CC3)CN4CC(C4)C(=O)O)C)OC
• Recent EU Clinical Trials: A Phase III, Randomized, Double-Blind, Double Dummy, Multicenter Trial Comparing the Efficacy and Safety of 2 Doses of Daily Oral ONO 4641 (0.05 mg and 0.1 mg) versus Interferon-β-1a 30 μg IM Weekly in Subjects with Relapsing Multiple Sclerosis
• Description: Ceralifimod is an agonist of the sphingosine-1-phosphate (S1P) receptors S1P1 and S1P5 (Kis = 0.626 and 0.574 nM, respectively). It is selective for S1P1 and S1P5 over S1P2-4 (Kis = >5,450, >5,630, and 28.8 nM, respectively). Ceralifimod induces calcium influx in CHO-K1 cells overexpressing S1P1 (EC50 = 1 nM) and cAMP accumulation in CHO-K1 cells overexpressing S1P1 or S1P5 (EC50s = 0.027 and 0.33 nM, respectively). In vivo, ceralifimod (0.03 and 0.1 mg/kg) reduces paw edema in a rat model of collagen induced arthritis (CIA). It also delays disease onset and inhibits lymphocyte infiltration of the spinal cord in a rat model of experimental autoimmune encephalomyelitis (EAE) and prevents disease relapse in a non-obese diabetic mouse model of relapsing-remitting EAE.

Technology Process of Ceralifimod

There total 10 articles about Ceralifimod which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 74.45%

methyl 1-({6-[(2-methoxy-4-propylbenzyl)oxy]-1-methyl-3,4-dihydro-2-naphthalenyl}methyl)-3-azetidinecarboxylate → 1-({6-[(2-methoxy-4-propylbenzyl)oxy]-1-methyl-3,4-dihydronaphthalen-2-yl}methyl)azetidine-3-carboxylic acid (891859-12-4)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; methanol; water; at 0 - 20 ℃; for 3h;

DOI:10.1021/acs.jmedchem.7b00785

Reference yield:

(2-methoxy-4-propylphenyl)methanol (891859-11-3) + 1-(bromomethyl)-2-methoxy-4-propylbenzene (891859-13-5) → 1-({6-[(2-methoxy-4-propylbenzyl)oxy]-1-methyl-3,4-dihydronaphthalen-2-yl}methyl)azetidine-3-carboxylic acid (891859-12-4)

Guidance literature:

With phosphorus tribromide; In diethyl ether;

Reference yield:

ethyl 1-({6-[(2-methoxy-4-propylbenzyl)oxy]-1-methyl-3,4-dihydro-2-naphthalenyl}methyl)-3-azetidinecarboxylate → 1-({6-[(2-methoxy-4-propylbenzyl)oxy]-1-methyl-3,4-dihydronaphthalen-2-yl}methyl)azetidine-3-carboxylic acid (891859-12-4)

Guidance literature:

ethyl 1-({6-[(2-methoxy-4-propylbenzyl)oxy]-1-methyl-3,4-dihydro-2-naphthalenyl}methyl)-3-azetidinecarboxylate; With water; sodium hydroxide; In methanol; at 40 ℃; for 2h;

With hydrogenchloride; In methanol; water; Product distribution / selectivity;

upstream raw materials:

(2-methoxy-4-propylphenyl)methanol

1-(bromomethyl)-2-methoxy-4-propylbenzene

3-n-propylphenol

2-hydroxy-4-propylbenzoic acid

Refernces

• 1、 -. "AMINOCARBOXYLIC ACID DERIVATIVE AND MEDICINAL USE THEREOF". . . Retrieved 2008/06/13.