248281-84-7 Usage
Description
CIVENTICHEM CV-4057, also known as Laquinimod, is an immunomodulator with the chemical formula (248281-84-7). It functions by inhibiting inflammation and autoimmunity through the activation of the aryl hydrocarbon receptor (AhR). Laquinimod has been extensively studied for its potential therapeutic applications in various diseases, including multiple sclerosis and Huntington's disease.
Uses
Used in Pharmaceutical Industry:
CIVENTICHEM CV-4057 is used as an immunomodulator for the treatment of multiple sclerosis. It has demonstrated efficacy in reducing inflammation and autoimmunity, which are key factors in the progression of the disease.
CIVENTICHEM CV-4057 is also used as a potential treatment for Huntington's disease. It has shown positive results in disease models, suggesting its potential to alleviate symptoms and improve the quality of life for patients.
Additionally, due to its immunomodulatory properties, CIVENTICHEM CV-4057 may have applications in other areas of medicine where inflammation and autoimmunity play a significant role, such as autoimmune disorders and certain types of cancer. Further research and clinical trials would be necessary to explore these potential applications fully.
in vitro
abr-215062 was shown to completely inhibit the development of murine acute experimental autoimmune encephalomyelitis (eae) [1].
in vivo
abr-215062 dose-dependently inhibited disease and showed better disease inhibitory effects as compared to roquinimex (linomide). furthermore, abr-215062 inhibited the inflammation of both cd4+ t cells and macrophages into central nervous tissues [2].
References
J?nsson et al. (2004), Synthesis and Biological Evaluation of New 1,2-Dihydro-4-hydroxy-2-oxo-3-quinolinecarboxamides for Treatment of Autoimmune Disorders: Structure-Activity Relationship; Med. Chem. 47 2075
Rothhammer et al. (2021); Aryl Hydrocarbon Receptor Activation in Astrocytes by Laquinimod Ameliorates Autoimmune Inflammation in the CNS, Neurol. Neuroimmunol. Neuroinflamm., 8 e946
Pitarokoili et al. (2014), Laquinimod exerts strong clinical and immunomodulatory effects in Lewis rat experimental autoimmune neuritis; Neuroimmunol., 274 38
Ott et al. (2019), Laquinimod, a prototypic quinoline-3-carboxamide and aryl hydrocarbon receptor agonist, utilizes CD155-mediated natural killer/dendritic cell interaction to suppress CNS autoimmunity; Neuroinflammation, 16 49
Kaye et al. (2016), Laquinimod arrests experimental autoimmune encephalitis by activating the aryl hydrocarbon receptor; Natl. Acad. Sci. USA., 113 E6145
Th?ne and Linker (2016), Laquinimod in the treatment of multiple sclerosis: a review of the data so far; Drug Des. Devel. Ther., 10 1111
Dobson et al. (2016), Laquinimod dampens hyperactive cytokine production in Huntington’s disease patient myeloid cells; Neurochem., 137 782
Garcia-Miralles et al. (2016), Laquinimod rescues striatal, cortical and white matter pathology and results in modest behavioural improvements in the YAC128 model of Huntington disease; Rep., 6 31652
Check Digit Verification of cas no
The CAS Registry Mumber 248281-84-7 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 2,4,8,2,8 and 1 respectively; the second part has 2 digits, 8 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 248281-84:
(8*2)+(7*4)+(6*8)+(5*2)+(4*8)+(3*1)+(2*8)+(1*4)=157
157 % 10 = 7
So 248281-84-7 is a valid CAS Registry Number.
InChI:InChI=1/C19H17ClN2O3/c1-3-22(12-8-5-4-6-9-12)19(25)16-17(23)15-13(20)10-7-11-14(15)21(2)18(16)24/h4-11,23H,3H2,1-2H3
248281-84-7Relevant articles and documents
An Efficient Method for the Synthesis of Laquinimod
Huang, Yanyan,Feng, Ying,Gao, Wensheng,Zhang, Chao,Chen, Ligong
, p. 437 - 440 (2016/04/19)
Laquinimod, 5-chloro-1,2-dihydro-N-ethyl-4-hydroxy-1-methyl-2-oxo-N- phenyl-3-quinoline carboxamide, is an oral drug in clinical trials for the treatment of multiple sclerosis. An efficient synthetic method for laquinimod from 2-amino-6-chlorobenzoic acid via four steps was established. The overall yield of laquinimod is up to 82% as compared with 70% reported in literature. It has also been demonstrated that green reagent dimethyl carbonate is not suitable for the N-methylation of 5-chloroisatoic anhydride owing to the ring-cleavage reaction induced by the generated methanol. The ring-cleavage by-products were isolated and characterized by 1H-NMR and 13C-NMR. In addition, in the study of laquinimod derivatives, we found that 5-chloro-1,2-dihydro-N-ethyl-4-hydroxy-1-methyl-2-oxo-N-phenyl-3-quinoline carboxamide (laquinimod) was obtained in much higher yield than 7-chloro-1,2-dihydro-N-ethyl-4-hydroxy-1-methyl-2-oxo-N-phenyl-3-quinoline carboxamide under the same reaction conditions, and it is possibly attributed to a neighboring group effect.
INTERMEDIATE COMPOUNDS AND PROCESSES FOR THE PREPARATION OF QUINOLINE DERIVATIVES SUCH AS LAQUINIMOD SODIUM
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Page/Page column 27, (2012/06/15)
The present invention relates to processes for the preparation of quinoline-3 -carboxamide derivatives, such as sodium 5-chloro-3-(ethylphenylcarbamoyl)-l-methyl-2- oxo-l,2-dihydroquinolin-4-olate (Laquinimod sodium). The present invention further relates to intermediates formed in such processes.
1,2-DIHYDRO-4-HYDROXY-2-OXO-QUINOLINE-3-CARBOXANILIDES AS AHR ACTIVATORS.
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Page/Page column 30, (2012/05/04)
The present invention relates to compounds which are 1, 2-dihydro-4- hydroxy-2-oxo-quinoline-3-carboxanilides, their thieno-pyridone analogs, and prodrugs thereof. This invention specifically relates to such derivatives containing an N-hydrogen in the carboxanilide moiety and which exhibit modulating activity towards the aromatic hydrocarbon receptor (AhR), and, specifically, also to prodrugs thereof. The present invention also relates to use of said compounds as a medicament, and for the treatment of cancer, autoimmune disorders and other disorders with an immunological component, and a pharmaceutical composition comprising one or more of said compounds and a method of treatment.
