40707-01-5

Usage

Uses

Used in Pharmaceutical Industry:
5-CHLORO-1-METHYL-1H-BENZO[D][1,3]OXAZINE-2,4-DIONE is used as an intermediate in the synthesis of pharmaceutical compounds for its unique chemical structure and properties. It can be utilized in the development of new drugs, particularly in the areas of medicine and medicinal chemistry.
Used in Chemical Synthesis:
In the field of chemical synthesis, 5-CHLORO-1-METHYL-1H-BENZO[D][1,3]OXAZINE-2,4-DIONE serves as a key building block for the creation of various complex organic molecules. Its reactivity and structural features make it a valuable component in the synthesis of specialty chemicals and advanced materials.
Used in Materials Science:
5-CHLORO-1-METHYL-1H-BENZO[D][1,3]OXAZINE-2,4-DIONE is used as a component in the development of new materials with specific properties. Its incorporation into polymers, coatings, or other materials can enhance their performance, durability, or functionality in various applications.
Used in Research and Development:
As a heterocyclic organic compound with unique structural features, 5-CHLORO-1-METHYL-1H-BENZO[D][1,3]OXAZINE-2,4-DIONE is used in research and development for exploring its potential applications and properties. It can contribute to the advancement of knowledge in chemistry, materials science, and related fields.
It is important to handle and use 5-CHLORO-1-METHYL-1H-BENZO[D][1,3]OXAZINE-2,4-DIONE with care, following proper safety protocols and guidelines due to its potential applications and reactivity.

InChI:InChI=1/C9H6ClNO3/c1-11-6-4-2-3-5(10)7(6)8(12)14-9(11)13/h2-4H,1H3

Upstream product

• 20829-96-3 5-chloro-1H-benzo[d][1,3]oxazine-2,4-dione 
• 616-38-6 carbonic acid dimethyl ester 
• 2148-56-3 2-chloro-6-aminobenzoic acid 
• 77-78-1 dimethyl sulfate 
• 74-88-4 methyl iodide 

Downstream Products

• 248282-10-2 5-chloro-1,2-dihydro-4-hydroxy-1-methyl-2-oxo-3-quinolinecarboxylic acid ethyl ester 
• 637027-41-9 1,2-dihydro-4-hydroxy-5-chloro-1-methyl-2-oxo-quinoline-3-carboxylic acid methyl ester 
• 248281-84-7 laquinimod 
• 1383427-58-4 ingenol-5,20-acetonide-3-(2-chloro-6-methylamino-benzoate) 

Relevant academic research and scientific papers

An Efficient Method for the Synthesis of Laquinimod

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.

Synthesis, regioselectivity, and DFT analysis of new antioxidant pyrazolo[4,3-c]quinoline-3,4-diones

The condensation of hydrazine, N-methylhydrazine, and N-phenylhydrazine with ethyl 4-chloro-2-oxo- 1,2-dihydroquinoline-3-carboxylate derivatives has been investigated. As a result, 12 new antioxidant pyrazolo[4,3- c]quinolin-3,4-diones were obtained with good to high yields. When two cross-products could be possible, only one isomer bearing the methyl or the phenyl group at the N1 position is isolated and unequivocally characterized using 1D and 2D NMR techniques, FT-IR, and combustion analyses. DFT analysis of the reaction mechanism was carried out in the Pearson’s hard soft acid base framework, confirming the assigned structure to the observed pyrazolo[4,3-c]quinolin-3,4-diones. These calculations indicate a favored kinetic control for the synthesized pyrazolo[4,3- c]quinolin-3,4-diones compared to its possible regioisomer.

Heterocyclic GSK-3 Allosteric Modulators

The present invention relates to heterocyclic substituted quinoline derivatives as allosteric inhibitors of the glycogen synthase kinase-3 (GSK-3) enzyme. Therefore, these compounds are useful for the manufacturing of a medicament designed for the treatme

Synthesis, biological evaluation and SAR of 3-benzoates of ingenol for treatment of actinic keratosis and non-melanoma skin cancer

Ingenol 3-benzoates were investigated with respect to chemical stability, pro-inflammatory effects, cell death induction and PKCδ activation. A correlation between structure, chemical stability and biological activity was found and compared to ingenol mebutate (ingenol 3-angelate) used for field treatment of actinic keratosis. We also provided further support for involvement of PKCδ for induction of oxidative burst and cytokine release. Molecular modeling and dynamics calculations corroborated the essential interactions between key compounds and C1 domain of PKCδ.

HIGHLY PURE LAQUINIMOD OR A PHARMACEUTICALLY ACCEPTABLE SALT THEREOF

Provided herein is an impurity of laquinimod, N-ethyl-N-phenyl-1,2-dihydro-4-hydroxy-1-methyl-2-oxoquinoline-3-carboxamide (deschloro laquinimod impurity), and process for preparation and isolation thereof. Provided further herein is a highly pure laquinimod or a pharmaceutically acceptable salt thereof substantially free of deschloro laquinimod impurity, processes for the preparation thereof, and pharmaceutical compositions comprising highly pure laquinimod or a pharmaceutically acceptable salt thereof substantially free of deschloro laquinimod impurity.

3-ACYL-INGENOLS II

The invention relates to compounds of general formula I, (I), wherein R is wherein R is aryl substituted by R3; or R is (C3-Ci3)-cycloalkyl, (C3-Ci3)- cycloalkenyl or (C7-Ci3)-cycloalkynyl optionally substituted by R4; and pharmaceutically acceptable salts, hydrates, or solvates thereof, for use -alone or in combination with one or more other pharmaceutically active compounds- in therapy, for preventing, treating or ameliorating diseases or conditions responsive to stimulation of neutrophil oxidative burst, responsive to stimulation of keratinocyte IL-8 release or responsive to induction of necrosis.

Synthesis, biological assessment and molecular modeling of new dihydroquinoline-3-carboxamides and dihydroquinoline-3-carbohydrazide derivatives as cholinesterase inhibitors, and Ca channel antagonists

The synthesis, biological evaluation, and molecular modeling of new 4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxamides(4), 4-hydroxy-2-oxo-1,2- dihydroquinoline-3-carbohydrazide (6), and some hexahydropyrimido[5,4-c] quinoline-2,5-diones (9) produced earlier by our laboratory, as AChE/BuChE inhibitors, is described. From these analyses compound 4c resulted equipotent regarding the inhibition of cholinesterases'; inhibitors 6k, 9a, 9b were selective for AChE, whereas product 4d proved selective for BuChE. Docking analysis has been carry out in order to identify the binding mode in the active site, and to explain the observed selectivities. Only compound 9a has been shown to decrease K+-induced calcium signals in bovine chromaffin cells.

HIGHLY PURE LAQUINIMOD OR A PHARMACEUTICALLY ACCEPTABLE SALT THEREOF

Provided herein is an impurity of laquinimod, N-ethyl-N-phenyl-1,2-dihydro-4-hydroxy-1- methyl-2-oxoquinoline-3-carboxamide (deschloro laquinimod impurity), and process for preparation and isolation thereof. Provided further herein is a highly pure laquinimod or a pharmaceutically acceptable salt thereof substantially free of deschloro laquinimod impurity, processes for the preparation thereof, and pharmaceutical compositions comprising highly pure laquinimod or a pharmaceutically acceptable salt thereof substantially free of deschloro laquinimod impurity.

2-OXO-1,2-DIHYDRO-QUINOLINE MODULATORS OF IMMUNE FUNCTION

The present invention relates to new 2-oxo-1,2-dihydro-quinoline modulators of immune function, pharmaceutical compositions thereof, and methods of use thereof.

Development of a practical and reliable synthesis of laquinimod

Laquinimod(5-chloro-1,2-dihydro-N-ethyl-4-hydroxy-1-methyl-2-oxo-N-phenyl- 3-quinoline carboxamide) is a drug candidate for treatment of Multiple Sclerosis. A short and industrially feasible process for the preparation of laquinimod starting from 2-amino-6-chlorobenzoic acid, in essentially four steps, is discussed. The key step is a novel reaction in which a methyl ester is converted to an amide in very high yield and with excellent purity. The present article elucidates the scale-up process along with safety aspects and the impurity profiles of the intermediates and product. Initial laboratory conditions are described as well as the changes made on transfer to pilot-plant scale.