5-[3-[(1S)-2,3-Dihydro-1-[(2-hydroxyethyl)amino]-1H-inden-4-yl]-1,2,4-oxadiazol-5-yl]-2-(1-methylethoxy)benzonitrile

5-[3-[(1S)-2,3-Dihydro-1-[(2-hydroxyethyl)amino]-1H-inden-4-yl]-1,2,4-oxadiazol-5-yl]-2-(1-methylethoxy)benzonitrile - Names and Identifiers

Name	Ozanimod
Synonyms	Ozanimod Ozanimod (RPC1063) (S)-5-(3-(1-((2-hydroxyethyl)amino)-2,3-dihydro-1H-inden-4-yl)-1,2,4-oxadiazol-5-yl)-2-isopropoxybenzonitrile 5-[3-[(1S)-2,3-Dihydro-1-[(2-hydroxyethyl)amino]-1H-inden-4-yl]-1,2,4-oxadiazol-5-yl]-2-(1-methylethoxy)benzonitrile Benzonitrile, 5-[3-[(1S)-2,3-dihydro-1-[(2-hydroxyethyl)aMino]-1H-inden-4-yl]-1,2,4-oxadiazol-5-yl]-2-(1-Methylethoxy)- (free base)
CAS	1306760-87-1
EINECS	814-246-9

5-[3-[(1S)-2,3-Dihydro-1-[(2-hydroxyethyl)amino]-1H-inden-4-yl]-1,2,4-oxadiazol-5-yl]-2-(1-methylethoxy)benzonitrile - Physico-chemical Properties

Molecular Formula	C23H24N4O3
Molar Mass	404.4617
Density	1.30±0.1 g/cm3(Predicted)
Melting Point	134-137°C
Boling Point	648.3±65.0 °C(Predicted)
Solubility	DMSO: ≥ 29 mg/mL
Appearance	Form Solid, color White to Off-White
pKa	14.73±0.10(Predicted)
Storage Condition	-20°C Freezer
Physical and Chemical Properties	Bioactive Ozanimod (RPC1063) is a selective oral S1P Receptor 1 regulator.
Use	Ozamod is mainly used in the treatment of multiple sclerosis, ulcerative colitis and Crohn's disease. Among them, multiple sclerosis and ulcerative colitis not only have a long course and a high incidence, but also require long-term medication. It can be seen that Ozamod's market capacity is huge and the prospects are promising.

5-[3-[(1S)-2,3-Dihydro-1-[(2-hydroxyethyl)amino]-1H-inden-4-yl]-1,2,4-oxadiazol-5-yl]-2-(1-methylethoxy)benzonitrile - Preparation solution concentration reference

	1mg	5mg	10mg
1 mM	2.472 ml	12.362 ml	24.724 ml
5 mM	0.494 ml	2.472 ml	4.945 ml
10 mM	0.247 ml	1.236 ml	2.472 ml
5 mM	0.049 ml	0.247 ml	0.494 ml

Last Update：2024-01-02 23:10:35

5-[3-[(1S)-2,3-Dihydro-1-[(2-hydroxyethyl)amino]-1H-inden-4-yl]-1,2,4-oxadiazol-5-yl]-2-(1-methylethoxy)benzonitrile - Nature

Solubility

DMSO (Slightly), Methanol (Slightly)

Last Update：2024-04-10 22:29:15

5-[3-[(1S)-2,3-Dihydro-1-[(2-hydroxyethyl)amino]-1H-inden-4-yl]-1,2,4-oxadiazol-5-yl]-2-(1-methylethoxy)benzonitrile - Uses and synthesis methods

Introduction

Ozamod is a potential sphingosine phosphate 1 receptor agonist for the treatment of multiple sclerosis (MS) and ulcerative colitis jointly developed by the American Scripps Research Institute and the American Celgene Company. It can induce peripheral blood lymphocyte isolation and reduce the number of activated lymphocytes circulating into the gastrointestinal tract. According to the detailed results of the consolidation period of TOUCHSTONE clinical trials, the clinical remission compliance or consolidation rate of patients in Ozamod treatment group was significantly higher than that in placebo group at week 32.

Ozamod is an agonist that binds to S1P1 and S1P5 receptors. Rodent experiments have shown that Ozanimo is effective against autoimmune diseases.

Preparation

To a solution of N,N-dimethylformamide (110 ml) of the compound of formula V (27.5g, 0.1 mol), carbodiimide (23.0g, 0.12 mol) and 1-hydroxybenzotriazole (16.2g, 0.12 mol) were added to the solution of the compound of formula V (20.5g, 0.1 mol) under nitrogen protection. Reacting at room temperature for 2 hours, then heating the reaction mixture to 80°C for 12 hours. The reaction mixture was cooled to room temperature and diluted with ethyl acetate (250 ml). The organic layer was washed with NaHCO3, water and brine. The combined organic layer is dried by MgSO4 and concentrated to produce 46.0 grams of white foam solid, the compound of formula VII, which can be directly used in the next reaction without purification.

Prospects for Development

The industry is also very optimistic about Ozamod's business prospects. Dr. StephenHanauer, medical director of Northwest Medical Digestive Health Center, said: "The consolidation data of this trial, together with the previously reported induction data, suggest that the oral drug Ozamod is expected to help patients with moderate to severe ulcerative colitis.

in vitro studies

In S1P1R-HEK293T cells, Ozanimod induce continuous internalization and degradation of S1P1R.

In vivo studies

In vitro, Ozanimod showed high oral bioavailability and volume distribution volume. In a MOG-induced EAE mouse model, Ozanimod (3 mg/kg, p.o.) inhibited clinical symptoms. In a rat TNBS model with inflammatory bowel disease, Ozanimod (1.2 mg/kg, p.o.) inhibited the incidence of clinical and histological disease. In the natural CD4 CD45Rbhi T cell adoptive transfer model, Ozanimod (1.2 mg/kg, p.o.) will also significantly reduce the severity of the disease by measuring inflammation, gland loss, hyperplasia, neutrophil infiltration and mucosal thickness.

Last Update：2024-04-10 22:29:15

5-[3-[(1S)-2,3-Dihydro-1-[(2-hydroxyethyl)amino]-1H-inden-4-yl]-1,2,4-oxadiazol-5-yl]-2-(1-methylethoxy)benzonitrile

Suzhou Biosyntech Co., Ltd

5-[3-[(1S)-2,3-Dihydro-1-[(2-hydroxyethyl)amino]-1H-inden-4-yl]-1,2,4-oxadiazol-5-yl]-2-(1-methylethoxy)benzonitrile

Ozanimod

CAS: 1306760-87-1

Molecular Formula: C23H24N4O3

5-[3-[(1S)-2,3-Dihydro-1-[(2-hydroxyethyl)amino]-1H-inden-4-yl]-1,2,4-oxadiazol-5-yl]-2-(1-methylethoxy)benzonitrile - Names and Identifiers

5-[3-[(1S)-2,3-Dihydro-1-[(2-hydroxyethyl)amino]-1H-inden-4-yl]-1,2,4-oxadiazol-5-yl]-2-(1-methylethoxy)benzonitrile - Physico-chemical Properties

5-[3-[(1S)-2,3-Dihydro-1-[(2-hydroxyethyl)amino]-1H-inden-4-yl]-1,2,4-oxadiazol-5-yl]-2-(1-methylethoxy)benzonitrile - Preparation solution concentration reference

5-[3-[(1S)-2,3-Dihydro-1-[(2-hydroxyethyl)amino]-1H-inden-4-yl]-1,2,4-oxadiazol-5-yl]-2-(1-methylethoxy)benzonitrile - Nature

5-[3-[(1S)-2,3-Dihydro-1-[(2-hydroxyethyl)amino]-1H-inden-4-yl]-1,2,4-oxadiazol-5-yl]-2-(1-methylethoxy)benzonitrile - Uses and synthesis methods

Supplier List

5-[3-[(1S)-2,3-Dihydro-1-[(2-hydroxyethyl)amino]-1H-inden-4-yl]-1,2,4-oxadiazol-5-yl]-2-(1-methylethoxy)benzonitrile Request for Quotation

Ozanimod

CAS: 1306760-87-1

Molecular Formula: C23H24N4O3

5-[3-[(1S)-2,3-Dihydro-1-[(2-hydroxyethyl)amino]-1H-inden-4-yl]-1,2,4-oxadiazol-5-yl]-2-(1-methylethoxy)benzonitrile - Names and Identifiers

5-[3-[(1S)-2,3-Dihydro-1-[(2-hydroxyethyl)amino]-1H-inden-4-yl]-1,2,4-oxadiazol-5-yl]-2-(1-methylethoxy)benzonitrile - Physico-chemical Properties

5-[3-[(1S)-2,3-Dihydro-1-[(2-hydroxyethyl)amino]-1H-inden-4-yl]-1,2,4-oxadiazol-5-yl]-2-(1-methylethoxy)benzonitrile - Preparation solution concentration reference

5-[3-[(1S)-2,3-Dihydro-1-[(2-hydroxyethyl)amino]-1H-inden-4-yl]-1,2,4-oxadiazol-5-yl]-2-(1-methylethoxy)benzonitrile - Nature

5-[3-[(1S)-2,3-Dihydro-1-[(2-hydroxyethyl)amino]-1H-inden-4-yl]-1,2,4-oxadiazol-5-yl]-2-(1-methylethoxy)benzonitrile - Uses and synthesis methods

Supplier List

5-[3-[(1S)-2,3-Dihydro-1-[(2-hydroxyethyl)amino]-1H-inden-4-yl]-1,2,4-oxadiazol-5-yl]-2-(1-methylethoxy)benzonitrile