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Research on heterocyclic compounds, XLI. 2-phenylimidazo[1,2- b]pyridazine-3-acetic derivatives: Synthesis and anti-inflammatory activity

The synthesis of a group of 2-phenylimidazo[1,2-b]pyridazine-3-acetic esters and acids is described. The structures of the new compounds are supported by 1H-NMR spectra. These compounds were tested in vivo for their anti-inflammatory, analgesic and ulcerogenic activity. All new compounds showed remarkable anti-inflammatory action in the carrageenan rat paw oedema (one third of that for indomethacin) but no significant analgesic activity in the acetic acid writhing test together with negligible ulcerogenic action, and were also found to be lacking inhibitory activity on cyclooxygenase in vitro.

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Reference£º
Pyridazine – Wikipedia,
Pyridazine | C4H4N1102 – PubChem

 

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6-CYCLOAMINO-3-(1H-PYRROLO[2,3-b]PYRIDIN-4-YL)IMIDAZO[1,2-b]PYRIDAZINE DERIVATIVES, PREPARATION THEREOF AND THERAPEUTIC USE THEREOF

The invention relates to 6-cycloamino-3-(1H-pyrrolo[2,3-b]pyridin-4-yl)imidazo[1,2-b]pyridazine derivatives corresponding to the general formula (I) in which R2 represents an aryl group optionally substituted with one or more halogen atoms or C1-6-alkyl, C1-6-alkyloxy, C1-6-alkylthio, C1-6-fluoroalkyl, C1-6-fluoroalkyloxy and ?CN groups or R2 represents a group chosen from C1-6-alkyl, C1-6-fluoroalkyl, C3-7-cycloalkyl or C3-7-cycloalkyl-C1-6-alkyl groups; A represents a C1-7-alkylene group; B represents a C1-7-alkylene group; L represents either a nitrogen atom optionally substituted with an Rc or Rd group, or a carbon atom substituted with an Re1 group and an Rd group or two Re2 groups; the carbon atoms of A and of B being optionally substituted with one or more Rf groups, which may be identical to or different from one another. Preparation process and therapeutic use.

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Reference£º
Pyridazine – Wikipedia,
Pyridazine | C4H4N1086 – PubChem

 

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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.66346-87-0,6-Chloro-5-methylpyridazin-3-amine,as a common compound, the synthetic route is as follows.

The reaction is performed underan argon-atmosphere. 6-Chloro-5-methylpyridazin-3-amine (3.00 g; 20.90 mmol), ie/f-butyl 4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-1 ,2,3,6- tetrahydropyridine-1 -carboxylate (7.1 1 g; 22.98 mmol) and sodium carbonate (2 mol/L, aq. solution; 41 .79 mL; 83.58 mmol) in 1 ,4-dioxane (150 mL) is purged with argon. After 5 minutes Xphos 2nd Gen. (0.49 g; 0.63 mmol) is added and the mixture is stirred over night in a sealed vial at 100C. The reaction mixture is concentrated under reduced pressure. The residue is taken up in water and extracted several times with EtOAc. The combined organic layers are washed with brine, dried over Na2S04, filtered and concentrated under reduced pressure. The residue is purified by silica gel chromatography (DCM/MeOH). (1086) Yield: 5.20 g (86%) ESI-MS: m/z = 291 [M+H]+ Rt(HPLC): 0.79 min (method 10), 66346-87-0

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Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HYDRA BIOSCIENCES, INC.; BOUYSSOU, Thierry; GOTTSCHLING, Dirk; HEINE, Niklas; SMITH KEENAN, Lana Louise; LOWE, Michael D.; RAZAVI, Hossein; SARKO, Christopher Ronald; SURPRENANT, Simon; TAKAHASHI, Hidenori; TURNER, Michael Robert; WU, Xinyuan; (182 pag.)WO2019/81637; (2019); A1;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem

 

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66346-87-0 6-Chloro-5-methylpyridazin-3-amine 12353663, apyridazine compound, is more and more widely used in various fields.

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66346-87-0, Example 65 Preparation of Intermediate 66 [0664] [0665] A mixture of intermediate 58 (293 mg, 0.958 mmol) and 6-chloro-5-methylpyridazin-3-amine (195 mg, 1.35 mmol) in 16 mL of ethanol was heated at 77 C. overnight. After cooling to room temperature the reaction mixture was concentrated under reduced pressure and the residue was purified via silica gel column chromatography (5-100% ethyl acetate in hexanes) to yield intermediate 66 (125 mg, 38%) as a white solid. [0666] LCMS m/z [M+H]+ C17H23ClN4O2 requires: 351.15. Found 351.12. [0667] 1H-NMR (CDCl3, 400 MHz): delta 7.76 (s, 1H), 7.62 (s, 1H), 5.57 (m, 1H), 4.09 (m, 1H), 2.89 (m, 1H), 2.52 (m, 1H), 2.45 (s, 3H), 1.86 (m, 1H), 1.70-1.30 (m, 4H), 1.47 (s, 9H).

66346-87-0 6-Chloro-5-methylpyridazin-3-amine 12353663, apyridazine compound, is more and more widely used in various fields.

Reference£º
Patent; Siegel, Dustin; Sperandio, David; Yang, Hai; Sangi, Michael; Parrish, Jay P.; Hui, Hon Chung; US2013/273037; (2013); A1;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem

 

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66346-87-0, 6-Chloro-5-methylpyridazin-3-amine is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,66346-87-0

EXAMPLE 36 Sodium hydride (60% dispersion in oil; 0.25 g) was added to a solution of 3-amino-6-chloro-5-methylpyridazine (0.36 g) in dry 1,2-dimethoxyethane (10 ml). When evolution of gas ceased, 5-dimethylamino-1-naphthalenesulphonyl chloride (0.67 g) was added and the reaction mixture was stirred for 45 minutes. 7% aqueous citric acid solution (10 ml) was added, the organic phase was separated and the aqueous layer was extracted with ethyl acetate (2*20 ml). The combined organic phases were washed with water (10 ml) and dried (MgSO4). Volatile material was removed by evaporation to give a gum which was triturated first with dichloromethane and then ether to give 5-dimethylamino-N-(6-chloro-5-methyl-3-pyridazinyl)-1-naphthalenesulphonamide (0.2 g), m.p. 110-112 C.; 1 H NMR (d6 -DMSO): 2.30 (s,3H), 2.8 (s,6H), 7.23 (d,1H), 7.52-7.7 (m,3H), 8.3-8.5 (m,3H); mass spectrum (+ve FAB, methanol/dichloromethane/NBA): 376 (M)+.

The synthetic route of 66346-87-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Zeneca Limited; US5861401; (1999); A;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem