pyrazoles-derivatives

On March 31, 2007, Jagadhani, S. G.; Kale, S. B.; Chaudhari, C. S.; Sangle, M. D.; Randhavane, P. V.; Karale, B. K. published an article.SDS of cas: 36640-53-6 The title of the article was Knoevenagel reactions of 3-formyl chromones and 4-formyl pyrazoles with pyrazolone by conventional and non-conventional methods. And the article contained the following:

3-Formyl chromones when heated with 1,2-dihydro-1-phenyl-3-propylpyrazol-5-one (I) in presence of acetic acid afforded the compounds 4-(4-oxo-4H-chromon-3-yl)methylene-1-phenyl-3-propyl-1H-pyrazol-5-(4H)-ones. 4-Formyl pyrazoles on treatment with compound I in presence of acetic acid gave compounds (4)-1-phenyl-4-((1-phenyl-1H-pyrazol-4-yl)methylene)-3-propyl-1H-pyrazol-5-(4H)-ones. These compounds are synthesized by traditional, microwave, and ultrasonic irradiations. The experimental process involved the reaction of 3-(Naphthalen-2-yl)-1-phenyl-1H-pyrazole-4-carbaldehyde(cas: 36640-53-6).SDS of cas: 36640-53-6

The Article related to formyl chromone condensation pyrazolone microwave ultrasonic irradiation, pyrazole formyl condensation pyrazolone microwave ultrasonic irradiation, chromonyl methylene pyrazolone preparation microwave ultrasonic irradiation, pyrazolyl methylene pyrazolone preparation and other aspects.SDS of cas: 36640-53-6

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

On April 13, 2017, Aiguade Bosch, Jose; Connolly, Stephen; Eastwood, Paul Robert; Gomez Castillo, Elena; Moreno Mollo, Immaculada Montserrat; Roberts, Richard Spurring; Sevilla Gomez, Sara published a patent.Application of 314021-93-7 The title of the patent was Preparation of bicyclic fused pyrimidinone and triazinone derivatives as new TRPA1 antagonists. And the patent contained the following:

The present invention relates to compounds of Formula I [G1 = C or N atom; G2, G3, G4, G5 = each independently C(Ra), N(Rb), or N; G6 = N, G7 = C atom, G8 = N atom, G9 = O atom; Ra = H, linear or branched C1-4 alkyl, halogen atom, linear or branched C1-4 alkoxy, linear or branched C1-4 haloalkyl, linear or branched C1-4 haloalkoxy, oxo, C3-7 cycloalkyl, cyano, amino, mono – or di(C1-4 alkyl)amino, or hydroxy; Rb = H or linear or branched C1-4 alkyl; L = (un)substituted linear or branched C2-4 alkylene, C(Rb):C(Rb), C3-7 cycloalkylene, (CH2)2-3-O, (CH2)1-2-C(O), (CH2)1-2-S, (CH2)1-2-S(O), CONH, CF2O, or 4- to 6-membered N-containing heterocyclylene, wherein at least one nitrogen atom is linked the G7 group; Q = each (un)substituted monocyclic or bicyclic C6-14 aryl or monocyclic or bicyclic 5- to 14-membered heteroaryl containing at least one heteroatom selected from N, O and S; or when Q = Ph, L together with Q form a 5- to 7-membered N-containing heterocyclyl fused to the Ph group; n = 0-1; the solid/dashed line = single or a double bond], pharmaceutically acceptable salts, solvates, N-oxides, tautomers, stereoisomers, or isotopically-labeled derivatives thereof:. These compounds are used in the treatment of a pathol. condition or disease susceptible to amelioration by TRPA1 channel inhibition or antagonism. The pathol. condition or disease is selected from acute and/or chronic pruritus, acute and/or chronic pain, inflammatory dermatol. diseases, respiratory disorders, gastrointestinal inflammatory disorders, and urinary tract disorders. Thus, a suspension of 0.040 g 5-methylquinazolin-4(3H)-one and 0.069 g potassium carbonate in 1.0 mL DMF was stirred at room temperature for 10 min, followed by adding a solution of 0.071 g 5-(chloromethyl)-3-[2-(4-chlorophenyl)ethyl]-1,2,4-oxadiazole in 0. 5 mL DMF, and the resulting mixture of was stirred for 3 h to give, after workup and flash chromatog., 72% 3-[[3-[2-(4-chlorophenyl)ethyl]-1,2,4-oxadiazol-5-yl]methyl]-5-methylquinazolin-4(3H)-one (II). II and 3-[[3-[2-(4-Chlorophenyl)ethyl]-1,2,4-oxadiazol-5-yl]methyl]-5-methylimidazo[5,1-f]-[1,2,4]triazin-4(3H)-one (III) inhibited the tetracycline-inducible human TRPA1 expression in CHO cells in a calcium flux assay with IC50 of 100-1,000 and <100 nM, resp. The experimental process involved the reaction of 1-Methyl-1H-pyrazolo[4,3-d]pyrimidin-7-ol(cas: 314021-93-7).Application of 314021-93-7

The Article related to fused pyrimidinone preparation trpa1 antagonist, bicyclic fused triazinone preparation trpa1 antagonist, transient receptor potential cation channel trpa trpa1 antagonist, acute chronic pruritus treatment bicyclic heterocycle, chronic acute pain treatment bicyclic heterocycle and other aspects.Application of 314021-93-7

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

On September 18, 2014, Nazare, Marc; Halland, Nis; Schmidt, Friedemann; Kleemann, Heinz-Werner; Weiss, Tilo; Saas, Joachim; Struebing, Carsten published a patent.Synthetic Route of 98138-75-1 The title of the patent was Preparation of N-[4-(azaindazol-6-yl)-phenyl]-sulfonamides as SGK1 inhibitors. And the patent contained the following:

The title compounds I [Ar = (un)substituted Ph, 5-6 membered monocyclic, aromatic, heterocyclic group which comprises 1-3 identical or different ring heteroatoms selected from the series consisting of N, O and S, and is bonded via a ring C atom; n = 0-2; X = N, CH; Z = a bond, O, S, (un)substituted NH; R1 = H, (un)substituted NH2, NHC(O)NH2, etc.; R2 = halo, alkyl, alkoxy, CN; R3 = H, alkyl, -alkyl-R (R = (un)substituted 3-12 membered, monocyclic or bicyclic, saturated, partially unsaturated or aromatic, cyclic group which comprises 0-3 identical or different ring heteroatoms selected from N, O and S)] which modulate protein kinase activity, specifically the activity of serum and glucocorticoid regulated kinase (SGK), in particular of serum and glucocorticoid regulated kinase isoform 1 (SGK-1, SGK1), and are suitable for the treatment of diseases in which SGK activity is inappropriate, for example degenerative joint disorders or inflammatory processes such as osteoarthritis or rheumatism, were prepared E.g., a multi-step synthesis of II, starting from 2,5-dichlorobenzenesulfonyl chloride and 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenylamine, was described. Exemplified compounds I were tested for serum and glucocorticoid-regulated kinase 1 (SGK-1) inhibitory activity (data given). The invention furthermore relates to processes for the preparation of compounds I, their use as pharmaceuticals, and pharmaceutical compositions comprising them. The experimental process involved the reaction of 6-Chloro-4-methoxy-1H-pyrazolo[3,4-d]pyrimidine(cas: 98138-75-1).Synthetic Route of 98138-75-1

The Article related to azaindazolylphenyl sulfonamide preparation sgk1 inhibitor antiinflammatory antirheumatic antiarthritic, degenerative joint disorder osteoarthritis treatment azaindazolylphenyl sulfonamide preparation, serum glucocorticoid regulated kinase sgk inhibitor azaindazolylphenyl sulfonamide preparation and other aspects.Synthetic Route of 98138-75-1

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

On December 7, 2006, Mansour, Tarek Suhayl; Venkatesan, Aranapakam Mudumbai published a patent.HPLC of Formula: 153597-59-2 The title of the patent was Bicyclic 6-alkylidene-penems as class-D β-lactamase inhibitors. And the patent contained the following:

Penems, such as I [R = H, alkali metal, C1-6 alkyl, C5-6 cycloalkyl, or substituted ester; A, B = H, heteroaryl, fused bicycles, fused tricycles, etc.], were prepared for use in pharmaceutical compositions as inhibitors of β-lactamases which are class-D enzymes that hydrolyze β-lactam antibiotics, and as such serve as the primary cause of bacterial resistance. The compounds of the present invention when combined with β-lactam antibiotics will provide an effective treatment against life threatening bacterial infections. Thus, (5R,6Z)-6-(7-methyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazin-2-ylmethylene)-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid sodium salt (II) was prepared via a coupling reaction of 7-methyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine-2-carboxaldehyde with (5R,6S)-6-bromo-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitrobenzyl ester. The prepared penems were assayed for microbial susceptibility against E. coli GC 2883, a class-D producing organism. The experimental process involved the reaction of Ethyl 6,7-dihydro-5H-pyrazolo[5,1-b][1,3]oxazine-2-carboxylate(cas: 153597-59-2).HPLC of Formula: 153597-59-2

The Article related to alkylidene penem derivative preparation beta lactamase inhibitor, beta lactam antibiotic alkylidene penem derivative preparation, antibacterial agent alkylidene penem derivative preparation beta lactamase inhibitor, bacterial infection treatment alkylidene penem preparation beta lactamase inhibitor and other aspects.HPLC of Formula: 153597-59-2

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

On July 1, 2021, Pinkerton, Anthony; Sergienko, Eduard; Kiyotsuka, Yohei; Kagechika, Katsuji; Kurosaki, Yasunobu; Arai, Yoshikazu; Nagamochi, Masatoshi; Ishibashi, Koutaro published a patent.Safety of 1-Methyl-1H-pyrazolo[4,3-d]pyrimidin-7-ol The title of the patent was Preparation of bicyclic heteroaryls, especially thienopyrimidines, as ectonucleotide pyrophosphatase/phosphodiesterase 1 (ENPP1) modulators. And the patent contained the following:

The invention is related to the preparation of bicyclic heteroaryl-based small mol. modulators of ectonucleotide pyrophosphatase/phosphodiesterase 1 (ENPP1), e.g., of formula I [B = aryl or a 5 or 6-membered heteroaryl; n = 0-3; X = (CH2)1-2; p = 0-3; Y1 = NR4, O; L1 = Y2L2, Y2L2L3; Y2 = a bond, CO; L2 = a bond, (un)substituted alk(en/yn)ylene, heteroalkylene, C2-C6 cycloalkylene; R1 = H, halo, CN, OH, etc.; R2 = H, COOH and derivatives, fluoroalkoxy, etc.; R3 = H, halo, SH and derivatives, NH2 and derivatives, etc.; R5 = independently at each occurrence H, NO2, CN, SO2NH2 and derivatives, etc.; R6 = independently at each occurrence halo, alk(en/yn)yl, etc.; ], their pharmaceutically acceptable salts and solvates , compositions containing them, and methods of using the compounds and compositions comprising the compounds for treating disorders associated with ENPP1, such as pseudogout. Thus, II was prepared by cyclization of Me 3-amino-4-methylthiophene-2-carboxylate with formamide, chlorination of 7-methylthieno[3,2-d]pyrimidin-4-ol with POCl3, amination of 4-chloro-7-methylthieno[3,2-d]pyrimidine with tert-Bu (piperidin-4-yl)carbamate, cleavage of tert-butoxycarbonyl group and benzylation of 1-(7-methylthieno[3,2-d]pyrimidin-4-yl)piperidin-4-amine with benzyl chloride. II inhibited ENPP1 in a TR-FRET assay (IC50 in the range of 0.1μM – 1.0μM). The experimental process involved the reaction of 1-Methyl-1H-pyrazolo[4,3-d]pyrimidin-7-ol(cas: 314021-93-7).Safety of 1-Methyl-1H-pyrazolo[4,3-d]pyrimidin-7-ol

The Article related to bicyclic heteroaryl preparation ectonucleotide pyrophosphatase phosphodiesterase 1 enpp1 inhibitor, thienopyrimidine pyrazolopyrimidine pyrazolopyridine thienopyridine preparation enpp1 inhibitor pseudogout antiarthritic, triazolopyrimidine isoxazolopyrimidine pyrazolopyridazine isothiazolopyrimidine preparation enpp1 inhibitor and other aspects.Safety of 1-Methyl-1H-pyrazolo[4,3-d]pyrimidin-7-ol

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

On March 31, 2016, Ashok, Dongamanti; Rangu, Kavitha; Hanumantha Rao, Velagapuri; Gundu, Srinivas; Srilata, Ballu; Vijjulatha, Manga published an article.COA of Formula: C20H14N2O The title of the article was Microwave-assisted synthesis, molecular docking and antimicrobial activity of novel 2-(3-aryl-1-phenyl-1H-pyrazol-4-yl)-8H-pyrano[2,3-f]chromen-4-ones. And the article contained the following:

A series of pyrano[2,3-f]chromenones I [Ar = C6H5, 4-BrC6H4, 3,4-(MeO)2C6H3, 2-naphthyl, etc.] was synthesized via microwave-assisted cyclization of chalcones II in the presence of iodine in DMSO. Precursor chalcones II were prepared by Claisen-Schmidt condensation of 1-(5-hydroxy-2H-chromen-6-yl)ethanone and substituted pyrazole aldehydes using KOH under microwave irradiation This approach for the preparation of pyrano[2,3-f]chromenones I offers the advantages of short reaction time (3-5 min), mild reaction conditions and high yields of products. The newly synthesized compounds I and II were tested in vitro for their antibacterial and antifungal activities. Among the tested compounds, compounds I [Ar = 4-ClC6H4, 4-HOC6H4, 3,4-(MeO)2C6H3] and II [Ar = 3-EtOC6H4] were found to be potent against tested bacterial strains whereas compounds I [Ar = 4-ClC6H4, 3,4-(MeO)2C6H3] and II [Ar = 4-EtOC6H4] were found to be potent against tested fungal strains. Furthermore, the synthesized compounds were subjected to mol. docking studies for the inhibition of enzyme DNA gyrase and compounds I [Ar = 4-HOC6H4, 4-EtOC6H4] showed promising dock score values. The in silico mol. docking results of compounds I and II were in accordance with the in vitro antimicrobial studies and they may be considered as good inhibitor of DNA gyrase. The experimental process involved the reaction of 3-(Naphthalen-2-yl)-1-phenyl-1H-pyrazole-4-carbaldehyde(cas: 36640-53-6).COA of Formula: C20H14N2O

The Article related to pyranochromenone pyrazolyl preparation antibacterial antifungal mol docking, hydroxychromenyl pyrazolyl propenone preparation oxidative cyclization microwave irradiation, pyrazole aldehyde hydroxychromenyl ethanone claisen schmidt condensation microwave irradiation, pyrazolyl hydroxychromenyl propenone antibacterial antifungal mol docking and other aspects.COA of Formula: C20H14N2O

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

On October 4, 2012, Vankayalapati, Hariprasad; Appalaneni, Rajendra P.; Reddy, Y. Venkata Krishna published a patent.COA of Formula: C7H8N4 The title of the patent was Preparation of substituted 5-(pyrazin-2-yl)-1H-pyrazolo[3,4-b]pyridine and pyrazolo[3,4-b]pyridine derivatives as protein kinase inhibitors. And the patent contained the following:

This invention relates to the title compounds I-III [X = N, CH; L1 = a bond, (un)substituted 6-membered aryl, heteroaryl, etc.; R1-R3 = H, halo, CN, etc.; Q = NH, O, S, etc.; L2 = IV (wherein X1 = N, CH; X2 = N, CH; X3 = N, CH; R10 = H, halo, CN, etc.)] which are inhibitors of constitutively activated Tyrosine Kinase-Like (TKL), CMGC protein kinases family members and can be useful in the treatment of Parkinson’s disease, Alzheimer’s disease, Down’s syndrome, Huntington’s disease, other neurodegenerative and central nervous system disorders, cancer, metabolic disorders and inflammatory diseases, and to methods for making them. Seventy title compounds were prepared and formulated. For example, a multi-step synthesis of V, starting from mucobromic acid, was described. Exemplified title compounds were tested in the LRRK2 kinase assay (data given). Also disclosed are pharmaceutical compositions including the title compounds and methods of inhibiting wild type and/or mutated protein kinase activities of these families and the treatment of disorders associated therewith using title compounds and pharmaceutical compositions including the title compounds The experimental process involved the reaction of 3-Methyl-1H-pyrazolo[3,4-b]pyridin-5-amine(cas: 1186608-73-0).COA of Formula: C7H8N4

The Article related to pyrazinylpyrazolopyridine pyrazolopyridine preparation protein kinase inhibitor antitumor antiinflammatory antiparkinsonian, parkinson’s alzheimer’s disease down’s syndrome treatment pyrazinylpyrazolopyridine pyrazolopyridine preparation, huntington’s disease neurodegenerative cns disorder treatment pyrazinylpyrazolopyridine pyrazolopyridine preparation and other aspects.COA of Formula: C7H8N4

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

On July 30, 2020, Tang, Guozhi; Li, Dongbo; Li, Liugen; Zha, Xianchan; Chen, Wenming; Wang, Shaomeng; Yang, Chao-Yie published a patent.Formula: C9H12N2O3 The title of the patent was Preparation of macrocyclic fused pyrazoles as Mcl-1 inhibitors. And the patent contained the following:

The title compounds represented by formula I [R = H or C1-6 alkyl; X = O, S, S(O), S(O)2, or (un)substituted NH; ring A = each (un)substituted 1,3-phenylene or 1,3-naphthalenylene; ring B = arylenyl and heteroarylenyl; ring C = each (un)substituted 1H-pyrazol-3,4-diyl or 1H-pyrazol-4,5-diyl; L1 = [C(R14a)(R14b)]s; L2 = [C(R14c)(R14d)]t; L3 = [C(R14c)(R14f)]v; R14a, R14b, R14d, R14f = each independently H or C1-4 alkyl; s = 2,3,4,5, or 6; t, v = each independently 1,2,3, or 4] or pharmaceutically acceptable salts or solvates thereof are prepared The compounds I are useful for treating a condition or disorder responsive to Mcl-1 inhibition such as cancer, a chronic autoimmune disorder, an inflammatory condition, a proliferative disorder, sepsis, or a viral infection. Thus, Et 7-[2-(bromomethyl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl]-6-chloro-3-[3-[[3-[(4-methoxybenzyl)thio]naphthalen-1-yl]oxy]propyl]-1-methyl-1H-indole-2-carboxylate underwent thioetherification with S-[[5-[[(tert-butyldimethylsilyl)oxy]methyl]-1-methyl-1H-pyrazol-3-yl]methyl] ethanethioate in the presence of K2CO3 in methanol/THF at room for 1 h to give 27% Et 7-[2-[[[[5-[[(tert-butyldimethylsilyl)oxy]methyl]-1-methyl-1H-pyrazol-3-yl]methyl]thio]methyl]-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl]-6-chloro-3-[3-[[3-[(4-methoxybenzyl)thio]naphthalen-1-yl]oxy]propyl]-1-methyl-1H-indole-2-carboxylate (II; Ra = 4-methoxybenzyl, Rb = tert-butyldimethylsilyloxy) which was treated with Bu4NF·3H2O in dry THF at room temperature for 2 h to give II (Ra = 4-methoxybenzyl, Rb = HO). Bromination of II (Ra = 4-methoxybenzyl, Rb = HO) with CBr4 and PPh3 in CH2Cl2 at room temperature for 3 h gave II (Ra = 4-methoxybenzyl, Rb = Br) as a brown oil which underwent debenzylation by treatment with triethylsilane and CF3CO2H in CH2Cl2 at room temperature overnight to give II (Ra = H, Rb = Br). Cyclization of II (Ra = H, Rb = Br) by treatment with K2CO3 in acetonitrile at room temperature for 3 h gave macrocyclic 7-(pyrrolo[1,2-b]pyrazol-3-yl)indole-2-carboxylic acid Et ester (III; Rc = Et) which was saponified with a mixture of 2 N aqueous NaOH solution, THF, and MeOH at room temperature for 5 h followed by acidification with 1 N aqueous HCl solution to give III (Rc = H) in 3% over 6 steps. III (Rc = H) showed IC50 of 15 nM against the competitive binding of a fluorescein labeled 21-residue Bid BH3 peptide (residues 79-99) [Swiss-Prot: P55957] to Mcl-1 protein. It showed IC50 of 437 and 123 nM against OPM2 and H929 cell, resp., in a cell viability assay. The experimental process involved the reaction of Ethyl 6,7-dihydro-5H-pyrazolo[5,1-b][1,3]oxazine-2-carboxylate(cas: 153597-59-2).Formula: C9H12N2O3

The Article related to indolyl fused pyrazole macrocyclic compound preparation mcl 1 inhibitor, macrocyclic fused pyrazole preparation mcl 1 inhibitor, cancer chronic autoimmune disorder treatment macrocyclic fused pyrazole preparation, inflammatory condition proliferative disorder macrocyclic fused pyrazole preparation, sepsis viral infection macrocyclic fused pyrazole preparation and other aspects.Formula: C9H12N2O3

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

On September 30, 2021, Ameriks, Michael K.; Laforteza, Brian Ngo; Ravula, Suchitra; Schiffer, Jamie M.; Stenne, Brice M. published a patent.Electric Literature of 143803-93-4 The title of the patent was Preparation of fused and bridged compounds as monoacylglycerol lipase modulators. And the patent contained the following:

This invention relates to the title compounds I [R1a = alkyl; R1b = H; or R1a and R1b taken together form (CH2)2-3; R2 = (un)substituted Ph, pyridyl, bicyclic heteroaryl; R3 = 1H-alkyl-pyrazolyl, 1H-haloalkyl-pyrazolyl, 1H-pyridyl-pyrazolyl, etc.; with the proviso], and pharmaceutically acceptable salts, isotopes, N-oxides, solvates, and stereoisomers thereof, to pharmaceutical compositions containing them, to methods of making them, and to methods of using them including methods for treating disease states, disorders, and conditions associated with MGL modulation, such as those associated with pain, psychiatric disorders, neurol. disorders (including, but not limited to major depressive disorder, treatment resistant depression, anxious depression, autism spectrum disorders, Asperger syndrome, bipolar disorder), cancers and eye conditions. E.g., a multi-step synthesis of (S)-II, starting from Et L-alaninate hydrochloride and Et 4-bromobutanoate, was described. Exemplified compounds I were tested for their in vitro activity of MGL (data given for representative compounds I). The experimental process involved the reaction of 4-Methylpyrazolo[1,5-a]pyridine-3-carboxylic acid(cas: 143803-93-4).Electric Literature of 143803-93-4

The Article related to analgesics, antidepressants, antitumor agents, anxiety disorders (anxious depression), anxiolytics, asperger syndrome, bipolar disorder, depression (treatment-resistant), eye disease and other aspects.Electric Literature of 143803-93-4

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics