854107-53-2

Usage

Uses

Used in Pharmaceutical Industry:
3-(2-Methylphenyl)-2-((Z)-propylimino)thiazolidin-4-one is used as a potential therapeutic agent for various conditions due to its anti-inflammatory and analgesic properties. Its ability to modulate inflammatory responses and alleviate pain makes it a promising candidate for the development of new drugs to treat inflammatory and pain-related disorders.
Used in Neurodegenerative Disorder Treatment:
In the field of neurodegenerative disorders, 3-(2-Methylphenyl)-2-((Z)-propylimino)thiazolidin-4-one is used as a potential neuroprotective agent. Its neuroprotective effects may help in the treatment of conditions such as Alzheimer's disease, Parkinson's disease, and other disorders characterized by neuronal degeneration.
Used in Antioxidant Formulations:
3-(2-Methylphenyl)-2-((Z)-propylimino)thiazolidin-4-one is used as an antioxidant in various formulations. Its antioxidant potential can help protect cells from oxidative stress and damage, which is implicated in numerous diseases and aging processes. This property makes it a valuable component in the development of antioxidant therapies and supplements.
Overall, 3-(2-Methylphenyl)-2-((Z)-propylimino)thiazolidin-4-one is a versatile compound with a wide range of potential applications in the pharmaceutical and healthcare industries. Its unique structure and biological activities make it a promising candidate for further research and development in drug discovery and therapeutic applications.

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Relevant academic research and scientific papers

Discovery of super soft-drug modulators of sphingosine-1-phosphate receptor 1

The oral S1PR1 agonist ponesimod demonstrated substantial efficacy in a phase II clinical trial of psoriasis. Unfortunately, systemic side effects were observed, which included lymphopenia and transient bradycardia. We sought to develop a topical soft-drug S1PR1 agonist with an improved therapeutic index. By modifying ponesimod, we discovered an ester series of S1PR agonists. To increase metabolic instability in plasma we synthesised esters described as specific substrates for paraoxonase and butyrylcholinesterases, esterases present in human plasma.

Discovery of Soft-Drug Topical Tool Modulators of Sphingosine-1-phosphate Receptor 1 (S1PR1)

In order to study the role of S1PRs in inflammatory skin disease, S1PR modulators are dosed orally and topically in animal models of disease. The topical application of S1PR modulators in these models may, however, lead to systemic drug concentrations, wh

PROCESS FOR THE PREPARATION OF|(2Z,5Z)-5-(3-CHLORO-4-((R)-2,3-DIHYDROXYPROPOXY)BENZYLIDENE)-2-(PROPYLIMINO)-3-|(O-TOLYL)THIAZOLIDIN-4-ONE AND INTERMEDIATE USED IN SAID PROCESS

The present invention relates to a new process for the preparation of (2Z,5Z)-5-(3-chloro-4- ((R)-2,3-dihydroxypropoxy)benzylidene)-2-(propylimino)-3-(o-tolyl)thiazolidin-4-one and to the new intermediate (R)-3-chloro-4-(2,3-dihydroxypropoxy)-benzaldehyde used in this process. (2Z,5Z)-5-(3-Chloro-4-((R)-2,3-dihydroxypropoxy)benzylidene)-2-(propylimino)-3- (o-tolyl)thiazolidin-4-one is described in WO 2005/054215 to act as an immunosuppressive agent. The present invention further also relates to a new process for the preparation of (R)-3-chloro-4-(2,3-dihydroxypropoxy)-benzaldehyde.

2-Imino-thiazolidin-4-one derivatives as potent, orally active S1P 1 receptor agonists

Sphingosine-1-phosphate (S1P) is a widespread lysophospholipid which displays a wealth of biological effects. Extracellular S1P conveys its activity through five specific G-protein coupled receptors numbered S1P1 through S1P5. Agonists of the S1P1 receptor block the egress of T-lymphocytes from thymus and lymphoid organs and hold promise for the oral treatment of autoimmune disorders. Here, we report on the discovery and detailed structure-activity relationships of a novel class of S1P1 receptor agonists based on the 2-imino-thiazolidin-4-one scaffold. Compound 8bo (ACT-128800) emerged from this series and is a potent, selective, and orally active S1P1 receptor agonist selected for clinical development. In the rat, maximal reduction of circulating lymphocytes was reached at a dose of 3 mg/kg. The duration of lymphocyte sequestration was dose dependent. At a dose of 100 mg/kg, the effect on lymphocyte counts was fully reversible within less than 36 h. Pharmacokinetic investigation of 8bo in beagle dogs suggests that the compound is suitable for once daily dosing in humans.

NEW PROCESS FOR THE PREPARATION OF 2-IMINO-THIAZOLIDIN-4-ONE DERIVATIVES

The present invention relates to a new process for the preparation of 2-imino- thiazolidin-4-one compounds of the Formula (I) and (II) and to compounds of Formula (II) as such. The present compounds of Formula (II) can be used as intermediates in the preparation of thiazolidin-4-one derivatives of the General Formula (II), said derivatives being described in WO 2005/054215. These compounds of General Formula (II) are described in WO 2005/054215 to act as immunosuppressive agents.

5-(BENZ- (Z) -YLIDENE) -THIAZOLIDIN-4-ONE DERIVATIVES AS IMMUNOSUPPRESSANT AGENTS

The invention relates to pharmaceutical compositions containing at least one 5- (benz- (Z) -ylidene-thiazolidin-4-one derivative (I), to prevent or treat disorders associated with an activated immune system. Furthermore, the invention relates to novel thi