5754-17-6

Usage

Uses

Used in Research and Development:
3,6-Dihydroxy-4,5-dimethylpyridazine is used as a research chemical for its potential applications in the scientific community. It serves as a key intermediate in the synthesis of more complex organic and pharmaceutical compounds, contributing to the advancement of chemical research.
Used in Organic Synthesis:
In the field of organic chemistry, 3,6-Dihydroxy-4,5-dimethylpyridazine is used as an intermediate in the synthesis of various organic compounds. Its unique structure allows for further functionalization and modification, making it a versatile building block for creating novel molecules with specific properties and applications.
Used in Pharmaceutical Intermediates:
3,6-Dihydroxy-4,5-dimethylpyridazine also plays a crucial role in the pharmaceutical industry as an intermediate in the development of new drugs. Its structural features can be exploited to design and synthesize pharmaceutical compounds with desired therapeutic properties, potentially leading to the discovery of new medications for various diseases and conditions.

Synthesis

Hydrazine hydrochloride (58 g, 552 mmol) is dissolved in hot water (300 mL) and dimethyl maleic anhydride (58 g, 460 mmol) is added in portions and the suspension stirred at reflux for 16 h. The suspension is cooled down to room temperature and the precipitate is filtered, washed with water and dried at 40° C. under vacuum to yield 4,5-dimethyl-1,2-dihydro-pyridazine-3,6-dione (36) (64 g, 99%).

InChI:InChI=1/C6H8N2O2/c1-3-4(2)6(10)8-7-5(3)9/h1-2H3,(H,7,9)(H,8,10)

Upstream product

• 766-39-2 2,3-Dimethylmaleic anhydride 
• 63751-07-5 1-amino-3,4-dimethyl-pyrrole-2,5-dione 

Downstream Products

• 34584-69-5 3,6-dichloro-4,5-dimethylpyridazine 

Relevant academic research and scientific papers

One-step ring condensation of hydrazine derivatives and cyclic anhydrides

Hydroxypyridazinone and pyrroledione rings condensation in the reactions of hydrazine hydrate with citraconic, 2,3-dimethylmaleic, succinic and cis-cyclohexanedicarboxylic anhydrides have been conducted in the HCl aqueous solution. The pyridazine-ring condensation yields products unexpected for these conditions. They have been identified by 1H/13C NMR and X-ray diffraction. The course of the reaction toward the five- and six-membered ring condensation strongly depends on methyl and other substituents in the anhydrides and in hydrazine. The obtained products indicate that the ring condensation is controlled by the molecular strains and steric hindrances between the substituents in anhydrides and pyridazinone products. The condensation of cyclic anhydrides with hydrazines has been reduced to one-step reaction and its yield significantly increased.

TRIAZOLOPYRIDAZINES AS PAR1 INHIBITORS, PRODUCTION THEREOF, AND USE AS MEDICAMENTS

The invention relates to novel compounds of formula I where R1, R2, R3, R4, R5, R6, R7, R8, Q1, Q2 and Q3 are each as defined below. The compounds of formula I have antithrombotic activity and inhibit especially protease-activated receptor 1 (PAR1). The i

TRIAZOLIUM SALTS AS PAR1 INHIBITORS, PRODUCTION THEREOF, AND USE AS MEDICAMENTS

The invention relates to novel compounds of formula I where X, A?, Q1, Q2 Q3, R2, R3, R4, R5, R6, R7, R8 and R9 are each as defined below. The compounds of formula I have antithrombotic activity and inhibit especially protease-activated recepto

Organic Compounds as Smo Inhibitors

The present invention relates generally to novel compounds relating to the diagnosis and treatment of pathologies relating to the Hedgehog pathway, including but not limited to tumor formation, cancer, neoplasia, and non-malignant hyperproliferative disorders. The present invention includes novel compounds, novel compositions, methods of their use and methods of their manufacture, where such compounds are generally pharmacologically useful as agents in therapies whose mechanism of action involve methods of inhibiting tumorigenesis, tumor growth and tumor survival using agents that inhibit the Hedgehog and Smo signaling pathway.