- Synthesis method of 6-chloroimidazo[1, 2-b]pyridazine-3-carbonitrile
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The invention relates to a synthesis method of 6-chloroimidazo[1, 2b]pyridazine-3-carbonitrile, which comprises the following steps of 1, adding N, N-dimethylformamide dimethyl acetal into a reactor to react with 3-amino-6-chloropyridazine, thereby obtaining an N, N-dimethyl-N'-3-(6-chloro-pyridazine)yl-formamidine intermediate; 2, adding a solvent into the N, N-dimethyl-N'-3-(6-chloro-pyridazine)yl-formamidine intermediate obtained in the step 1, mixing, adding bromoacetonitrile, reacting, adding alkali liquor, standing, separating out solid, and filtering to obtain a solid mixture, 3, completely dissolving the solid mixture obtained in the step 4 in ethyl acetate, washing with water and saturated edible salt water, drying, filtering, and removing ethyl acetate to obtain a crude product of 6-chloroimidazo[1, 2-b]pyridazine-3-carbonitrile, and 4, recrystallizing the crude product of the 6-chloroimidazo[1, 2-b]pyridazine-3-carbonitrile, and filtering to obtain a pure product of the 6-chloroimidazo[1, 2-b] pyridazine-3-carbonitrile. The method is short in overall process time, and the obtained product is stable in quality and high in purity.
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Paragraph 0021-0032
(2021/02/06)
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- HERBICIDAL COMPOUNDS
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Compounds of the formula (I) wherein the substituents are as defined in claim 1, useful as a pesticides, especially as herbicides.
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Page/Page column 85-86
(2021/04/02)
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- Synthetic method of 6-chloroimidazo [1, 2-b]pyridazine-3-formic acid
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The invention relates to a synthetic method of 6-chloroimidazo [1, 2-b]pyridazine-3-formic acid. The synthetic method comprises the steps of reacting N,N-dimethylformamide dimethyl acetal and 3-amino-6-chloropyridazine at the temperature of 40 to 120 DEG C to obtain an intermediate; under an alkali action, reacting at the temperature of 65 to 140 DEG C, and carrying out rotary evaporation and concentration to obtain a 6-chloroimidazo [1,2-b]pyridazine-3-formic acid ethyl ester crude product; recrystallizing the crude product to obtain a pure product; under an alkali action, carrying out hydrolysis reaction in a certain solvent, finishing reaction, neutralizing through hydrochloric acid, carrying out suction filtration, and washing drying to obtain a 6-chloroimidazo [1, 2-b]pyridazine-3-formic acid pure product. The synthetic method provided by the invention is adopted for preparing the 6-chloroimidazo [1, 2-b]pyridazine-3-formic acid, so that the reaction raw materials can be obtained easily, the method is easy to operate and control and simple in aftertreatment, and the product has stable quality and high purity.
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Paragraph 0015; 0016; 0018; 0020; 0022; 0024; 0026; 0028
(2017/08/29)
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- TGF-Beta Inhibitors
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Disclosed are imidazole and thiazole compounds, as well as pharmaceutical compositions and methods of use thereof. One embodiment is a compound having the structure and pharmaceutically acceptable salts, prodrugs and N-oxides thereof (and solvates and hydrates thereof), wherein X, A, Z, R1 and R′ are as described herein. In certain embodiments, a compound disclosed herein inhibits TGF-β, and can be used to treat disease by blocking TGF-β signaling.
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Paragraph 0956-0957
(2016/09/26)
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- COMPOUNDS AND COMPOSITIONS AS TRK INHIBITORS
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The invention provides compounds, pharmaceutical compositions comprising such compounds and methods of using such compounds to treat or prevent diseases or disorders associated with abnormal or deregulated TRK kinase activity.
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Page/Page column 37
(2012/03/27)
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- HETEROCYCLIC HYDRAZONE COMPOUNDS AND THEIR USES TO TREAT CANCER AND INFLAMMATION
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The invention relates to compounds of formula (I) and salts thereof: wherein the substituents are as defined in the specification; a compound of formula (I) for use in the treatment of the human or animal body, in particular with regard to c-Met tyrosine kinase mediated diseases or conditions; the use of a compound of formula (I) for manufacturing a medicament for the treatment of such diseases; pharmaceutical compositions comprising a compound of the formula (I), optionally in the presence of a combination partner, and processes for the preparation of a compound of formula (I).
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Page/Page column 54-55
(2011/02/24)
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- HETEROCYCLIC OXIME COMPOUNDS
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The invention relates to compounds of formula (I) and salts thereof wherein the substituents are as defined in the specification; a compound of formula (I) for use in the treatment of the human or animal body, in particular with regard to c-Met tyrosine kinase mediated diseases or conditions; the use of a compound of formula (I) for manufacturing a medicament for the treatment of such diseases; pharmaceutical compositions comprising a compound of the formula (I), optionally in the presence of a combination partner, and processes for the preparation of a compound of formula (I).
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Page/Page column 65
(2011/04/13)
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- New adenosine receptor ligands and uses thereof
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The present invention provides new compounds with high affinity for adenosine A2A receptors. It also provides antagonists of adenosine A2A receptors and their use as medicaments for the treatment and/or prophylaxis of diseases and di
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Page/Page column 75
(2010/08/07)
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- IMIDAZO [1,2-B] PYRIDAZINE DERIVATIVES FOR THE TREATMENT OF C-MET TYROSINE KINASE MEDIATED DISEASE
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The invention relates to compounds of formula (I) and salts thereof, formula (I) wherein the substituents are as defined in the specification, the application of a compound of formula (I) in a process for the treatment of the human or animal body, in particular with regard to C-Met tyrosine kinase mediated disease; the use of a compound of formula (I) for manufacturing a medicament for the treatment of such diseases; pharamaceutical compositions comprising a compound of the formula (I), optionally in the presence of a combination partner; processes for the preparation of a compound of formula (I).
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Page/Page column 77
(2009/10/21)
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- Synthetic studies on condensed-azole derivatives. V. Synthesis and anti- asthmatic activities of ω-sulfamoylalkyloxy[1,2,4]triazolo[1,s-b]pyridazines
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A series of novel ([1,2,4]triazolo[1,5-b]pyridazin-6- yl)oxyalkylsulfonamides was synthesized and evaluated for the ability to inhibit platelet activating factor (PAF)-induced bronchoconstriction in guinea pigs. The compounds bearing a gem-dialkyl or a cycloalkylidene group at the 2 position of the sulfamoylpropyloxy group in the side chain and a methyl group at the 7 position were found to have potent activity. Among them, 2,2-diethyl-3-(7-methyl[l,2,4]-triazolo[1,5-b]pyridazin-6- yl)oxypropanesulfonamide (13) showed excellent anti-asthmatic activity. Compouds 13 may be of significant value in the treatment of asthma and other respiratory diseases. The structure-activity relationships in this series of compounds are discussed.
- Kuwahara, Masaaki,Kawano, Yasuhiko,Kajino, Masahiro,Ashida, Yasuko,Miyake, Akio
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p. 1447 - 1457
(2007/10/03)
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- The transformations of 4-heteroarylaminomethylene-5(4H)-oxazolones into dehydropeptide derivatives
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2-Phenyl-4-heteroarylaminomethylene-5(4H)-oxazolones 3, which were prepared from the corresponding N,N-dimethyl-N'-heteroarylformamidines 1 and hippuric acid 2 in acetic anhydride, react with amino acids giving dehydropeptide derivatives 4, 5, and 6 as products. Dehydration of N-protected peptides 7-10, containing glycine at the C-terminal, followed by the reaction with formamidines 1 gave 2-substituted-4-heteroarylaminomethylene-5(4H)-oxazolones 11-14.
- Aljaz-Rozic,Svete,Stanovnik
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p. 1605 - 1611
(2007/10/03)
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- TRANSFORMATION OF AMINES AND N-HETEROARYLFORMAMIDINES INTO ESTERS OF SUBSTITUTED β-AMINO-α,β-DEHYDRO-α-AMINO ACIDS
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Esters of substituted β-amino-α,β-dehydro-α-amino acids 5 were prepared either by transformation of N-heteroaryl-N,N-dimethylformamidines 2 with 3 into 4, followed by ring opening, or by treatment of primary or secondary amines 1 with 9.
- Stanovnik, Branko,Svete, Jurij,Tisler, Miha,Zorz, Lilijana,Hvala, Ales,Simonic, Igor
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p. 903 - 910
(2007/10/02)
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- Reactions of N-Heteroarylformamide Oximes and N-Heteroarylacetamide Oximes with N,N-Dimethylformamide Dimethyl Acetal. Synthesis of 2-Methyl-s-triazoloazines and N-Methylcyanoaminoazines
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N-Heteroarylformamide oximes 3 (R = H) were converted with N,N-dimethylformamide dimethyl acetal (DMFDMA) into N-heteroaryl-N-methylcyanoamino compounds 5, as the main products.In some instances N-heteroarylcyanoamino compounds 4, cyanoimino compounds 7, and some other products, such as 9 and 10 were also formed.On the other hand, N-heteroarylacetamide oximes 3 (R = CH3) were cyclized under the same reaction conditions into 2-methyl-s-triazoloazines (6).N-Heteroarylacetamide O-methyl oximes 11 and 12 were prepared from the corresponding acetamidines 2 (R = CH3) and O-methylhydroxylamine.
- Stanovnik, Branko,Stimac, Anton,Tisler, Miha,Vercek, Bojan
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p. 577 - 583
(2007/10/02)
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