Category: pyrazoles-derivatives

On March 3, 2022, Grall-Ulsemer, Sandra; Guba, Wolfgang; Lerner, Christian; Li, Mingming; Liu, Yongqiang; Rudolph, Markus; Schmitt, Sebastien; Urner, Lorenz; Wang, Yongguang; Wang, Min; Wang, Jianhua; Yang, Song; Zhou, Chengang; Mattei, Patrizio published a patent.Formula: C4H6N2O The title of the patent was Imidazole-pyrazole derivatives as antibacterials and their preparation. And the patent contained the following:

The invention provides imidazole-pyrazole derivatives having formula I, and pharmaceutically acceptable salts thereof. Further provided are pharmaceutical compositions including the compounds, processes of manufacturing the compounds and methods of using the compounds as medicaments, in particular methods of using the compounds as antibiotics for the treatment or prevention of bacterial infections and resulting diseases. Compounds of formula I wherein R1R2 are taken together to form substituted nitrogen-containing heterocyclyl; R1 is (un)substituted 3- to 14-membered heterocyclyl, (un)substituted 3- to 14-membered heterocyclyl-CO and (un)substituted 3- to 14-membered heterocyclyl-C1-6 alkyl; R2 is H and C1-6 alkyl; R3 is H, halo, C1-6 alkyl and C1-6 alkoxy; R4 and R6 are independently H, C1-6 alkyl, C1-6 alkoxy, CN, etc.; R5a, R5b and R5c are independently H, halo, OH, C1-6 alkyl, C1-6 alkoxy, etc.; R7 is H, C1-6 alkyl and C1-6 haloalkyl; A is 5- to 14-membered heteroaryl; and pharmaceutically acceptable salts thereof, are claimed. Example compound II was prepared by methylation of N-(3-chloro-4-(4-(piperidine-4-carbonyl)piperazine-1-carbonyl)phenyl)-5-(1-(5-methoxypyridin-2-yl)-3-(trifluoromethyl)-pyrazol-4-yl)-1-methyl-imidazole-2-carboxamide with Me iodide. The invention compounds were evaluated for their antibacterial activity. From the assay, it was determined that compound II exhibited IC90 value of 0.095μM. The experimental process involved the reaction of 5-Methoxy-1H-pyrazole(cas: 215610-30-3).Formula: C4H6N2O

The Article related to imidazole pyrazole preparation antibacterial, Heterocyclic Compounds (More Than One Hetero Atom): Imidazoles and other aspects.Formula: C4H6N2O

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

On September 13, 2007, Blake, James F.; Boyd, Steven Armen; Cohen, Frederick; De Meese, Jason; Fong, Kin Chiu; Gaudino, John J.; Kaplan, Tomas; Marlow, Allison L.; Seo, Jeongbeob; Thomas, Allen A.; Tian, Hongqi; Young, Wendy B. published a patent.Related Products of 924909-16-0 The title of the patent was Heterobicyclic pyrazole compounds as Met tyrosine kinase inhibitors and their preparation and use. And the patent contained the following:

The invention is related to the preparation of I and II [X = O, S, NH and derivatives; Z2, Z3 = independently CH and derivatives, N, wherein none or one of Z2, and Z3 = N; R1 = H, (un)substituted alk(en/yn)yl, (hetero)aryl, etc.; R2 = H, CF3, CN, SH and derivatives, SO2NH2 and derivatives, etc.; R3 = (un)substituted carbocyclyl, heterocyclyl, (hetero)/aryl] and their pharmaceutically acceptable salts which are useful for inhibiting receptor tyrosine kinases and for treating disorders mediated thereby. Methods of using compounds I and II and their stereoisomers, geometric isomers, tautomers, solvates, metabolites and pharmaceutically acceptable salts, for in vitro, in situ, and in vivo diagnosis, prevention or treatment of such disorders in mammalian cells, or associated pathol. conditions are disclosed. Thus, pyrazolopyridine III was prepared by a multi-step synthesis via 1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-ol intermediate which was obtained from 1-(4-methoxybenzyl)-1H-pyrazol-5-amine and Meldrum’s acid. Certain I and II had IC50’s < 1 μM in a c-Met enzyme assay. The experimental process involved the reaction of 1-(4-Methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-ol(cas: 924909-16-0).Related Products of 924909-16-0

The Article related to heterobicyclic pyrazole preparation tyrosine kinase inhibitor antiproliferative, pyrazolopyridine preparation met kinase inhibitor antitumor hyperproliferative disease, Heterocyclic Compounds (More Than One Hetero Atom): Pyrazoles and other aspects.Related Products of 924909-16-0

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

Salanouve, Elise; Retailleau, Pascal; Janin, Yves L. published an article in 2012, the title of the article was Few unexpected results from a Suzuki-Miyaura reaction.Recommanded Product: 215610-30-3 And the article contains the following content:

In the course of the synthesis of original anti-infectious compounds, we focused on the palladium-catalyzed Suzuki-Miyaura aryl-aryl coupling reaction between 2-(3-ethoxy-5-iodo-1H-pyrazol-1-yl)pyridine and phenylboronic acid. A study of the reaction products obtained under different conditions (various ligands and solvents) not only provided us with insights to optimize this reaction but also with a few side compounds, resulting from CH activation, along with the unexpected bis(3-ethoxy-1-(pyridin-2-yl)-1H-pyrazol-5-yl)palladium. Stoichiometric experiments with this remarkably stable biscyclopalladated reagent and Ph halides pointed out the occurrence of aryl-aryl coupling, possibly via palladium IV intermediates. The experimental process involved the reaction of 5-Methoxy-1H-pyrazole(cas: 215610-30-3).Recommanded Product: 215610-30-3

The Article related to bispyridinylpyrazolylpalladium preparation reaction aryl halide, palladium bispyridinylpyrazolyl preparation reaction aryl halide, side product suzuki miyaura reaction, Heterocyclic Compounds (More Than One Hetero Atom): Pyrazoles and other aspects.Recommanded Product: 215610-30-3

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

On June 6, 2008, McLaughlin, Mark; Marcantonio, Karen; Chen, Cheng-yi; Davies, Ian W. published an article.Quality Control of 3-Phenyl-1-(tetrahydro-2H-pyran-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole The title of the article was A Simple, Modular Method for the Synthesis of 3,4,5-Trisubstituted Pyrazoles. And the article contained the following:

A modular approach for the regiocontrolled preparation of pyrazoles bearing substituents on all three carbon atoms is described. Central to this method is the use of a switchable metal-directing group to enable sequential direct lithiation of the 3- and 5-positions of the pyrazole ring. Pyrazole boronic esters obtained from these lithiated intermediates can undergo efficient Suzuki cross-coupling under the developed nonaqueous conditions, which minimize undesirable protolytic deboronation. Halogenation of the 4-position provides the means for substitution at the remaining carbon atom. The experimental process involved the reaction of 3-Phenyl-1-(tetrahydro-2H-pyran-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole(cas: 1028092-65-0).Quality Control of 3-Phenyl-1-(tetrahydro-2H-pyran-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

The Article related to aryl pyrazole regioselective synthesis, pyrazole tetrahydropyranyl regioselective lithiation suzuki coupling aryl halide, tetrahydropyranyl metal directing group, Heterocyclic Compounds (More Than One Hetero Atom): Pyrazoles and other aspects.Quality Control of 3-Phenyl-1-(tetrahydro-2H-pyran-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

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

On December 31, 2014, Goel, Neelima; Drabu, Sushma; Afzal, Obaid; Bawa, Sandhya published an article.Reference of 3-(Naphthalen-2-yl)-1-phenyl-1H-pyrazole-4-carbaldehyde The title of the article was Antimicrobial screening and one-pot synthesis of 4-(substituted-anilinomethyl)-3-(2-naphthyl)-1-phenyl-1H-pyrazole derivatives. And the article contained the following:

A series of 4-(substituted-anilinomethyl)-3-(2-naphthyl)-1-phenyl-1H-pyrazole derivatives (4a-4k) were synthesized through direct reductive amination of 3-(naphthalen-2-yl)-1-phenyl-1H-pyrazole-4-carbaldehyde with various substituted aromatic amines using NaBH4 in the presence of I2 as reducing agent. The reaction was carried out in anhydrous methanol under neutral conditions at room temperature All 4-(substituted-anilinomethyl)-3-(2-naphthyl)-1-phenyl-1H-pyrazole derivatives (4a-4k) were tested in vitro for antifungal and antibacterial activities against different fungal and bacterial strains. Most of the compounds exhibited considerable antifungal activity, but poor antibacterial activity against the test strains. In the series compound 4e, 4g, 4j, and 4k, showed excellent antifungal activity against the fungal strain Aspergillus niger (MTCC) 281 and Aspergillus flavus MTCC 277 (% inhibition in the range of 47.7-58.9). The experimental process involved the reaction of 3-(Naphthalen-2-yl)-1-phenyl-1H-pyrazole-4-carbaldehyde(cas: 36640-53-6).Reference of 3-(Naphthalen-2-yl)-1-phenyl-1H-pyrazole-4-carbaldehyde

The Article related to pyrazole naphthyl anilinomethyl preparation antibacterial antifungal, antimicrobial activity, naphthalene, pyrazole, reductive amination, Heterocyclic Compounds (More Than One Hetero Atom): Pyrazoles and other aspects.Reference of 3-(Naphthalen-2-yl)-1-phenyl-1H-pyrazole-4-carbaldehyde

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

Xu, Li-Li; Zheng, Chang-Ji; Sun, Liang-Peng; Miao, Jing; Piao, Hu-Ri published an article in 2012, the title of the article was Synthesis of novel 1,3-diaryl pyrazole derivatives bearing rhodanine-3-fatty acid moieties as potential antibacterial agents.Electric Literature of 36640-53-6 And the article contains the following content:

In the present study, a series of 1,3-diarylpyrazole derivatives I [R = (un)substituted Ph, n = 1-5] bearing rhodanine-3-fatty acid moieties were synthesized and their antimicrobial activities were tested against various Gram-pos. and Gram-neg. bacteria. 1,3-Diaryl-4-formylpyrazoles were synthesized as key intermediates following a Vilsmeier-Haack strategy. Several compounds with an MIC of 2 μg/mL exhibited stronger antibacterial activity against the methicillin-resistant Staphylococcus aureus (MRSA) than the controls. None of the compounds showed any activity against Gram-neg. bacteria. The experimental process involved the reaction of 3-(Naphthalen-2-yl)-1-phenyl-1H-pyrazole-4-carbaldehyde(cas: 36640-53-6).Electric Literature of 36640-53-6

The Article related to pyrazole aryl rhodanine derivative preparation antibacterial, thiazolidinone thioxodiarylpyrazolylmethylene preparation antibacterial, Heterocyclic Compounds (More Than One Hetero Atom): Pyrazoles and other aspects.Electric Literature of 36640-53-6

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

On November 18, 2021, Vu, Binh; Dominique, Romyr; Li, Hongju; Fahr, Bruce; Good, Andrew published a patent.Recommanded Product: 1340372-11-3 The title of the patent was Preparation of heteroaryl-substituted indole derivatives for restoring mutant p53 function. And the patent contained the following:

Mutations in oncogenes and tumor suppressors contribute to the development and progression of cancer. The disclosure provided compounds of formula I capable of binding to mutant p53 and restoring the ability of the p53 mutant to bind DNA and activate downstream effectors involved in tumor suppression. Compounds of formula I [wherein X1 to X4 independently = N, O, S, (un)substituted C, etc.; X5 = CH, N, or (un)substituted NH; wherein at least one of X1 to X4 is a carbon atom connected to Q1; A = (un)substituted ring; Q1 = C=O, C=S, alkylene, etc.; m = 1, 2, 3, or 4; Y = N, O, or absent; R1 = alkyl, halo, (hetero)aryl, etc.; R2 = alkyl, alkenyl, aryl, etc.; R3 and R4 independently = alkyl, aryl, heteroaryl, etc.; R3 and R4 together with the nitrogen atom to which R3 and R4 are bound form a ring] and pharmaceutically acceptable salts thereof, are claimed and exemplified. Example compound II was prepared a multistep procedure (preparation given). Exemplified I were evaluated for DNA binding activity using recombinant His-tag Y220C p53 DBD protein and TR-FRET anal. with some invention candidates demonstrating SC150 results in the range of 0μM to less than 2μM. The disclosed compounds can be used to reduce the progression of cancers that contain a p53 mutation. The experimental process involved the reaction of 1-(Tetrahydro-2H-pyran-4-yl)-1H-pyrazole-4-carboxylic acid(cas: 1340372-11-3).Recommanded Product: 1340372-11-3

The Article related to heteroaryl indole preparation mutant p53 restoration cancer progression, dna binding oncogene p53 stabilization heteroaryl indole, Heterocyclic Compounds (More Than One Hetero Atom): Pyrimidines and Quinazolines and other aspects.Recommanded Product: 1340372-11-3

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

On September 10, 2020, Cregg, James Joseph; Buckl, Andreas; Aay, Naing; Tambo-Ong, Arlyn A.; Koltun, Elena S.; Gill, Adrian Liam; Thompson, Severin; Gliedt, Micah J. published a patent.Reference of 1-(Tetrahydro-2H-pyran-4-yl)-1H-pyrazole-4-carboxylic acid The title of the patent was Preparation of bicyclic heterocyclyl compounds as SOS1 modulators. And the patent contained the following:

The present disclosure is directed to the title compounds I [Q1 = CH or N; Q4 = CH, C, or N; each Q2 = (independently) CR1 or N (wherein one Q2 = N and the other Q2 = CR1); each Q3 and Q5 = (independently) (un)substituted CH2, NH, CO, O, S, or SO2; wherein at least one of Q1-Q5 = N, (un)substituted NH, O, or SO2; m = 0-3; n = 0-3; wherein when m = 0, then n is not 0; R1 = H, alkyl, halo, etc.; L2 = a bond, C(O), C(O)O, etc.; R2 = H, alkyl, cycloalkyl, etc.; R3 and R4 = (independently) H or alkyl optionally substituted with halo or OH; wherein at least one of R3 and R4 = H or wherein R3 and R4 together with the atom to which they are attached combine to form a 3-6 membered cycloalkyl; A = (un)substituted 6-membered aryl or 5-6 membered heteroaryl; with the proviso] or pharmaceutically acceptable salts, solvates, isomers, prodrugs, or tautomers thereof, that are modulators of SOS1 and their use in the treatment of disease. E.g., a multi-step synthesis of (1R)-II, starting from 2,4-dichloro-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidine and morpholine-4-carbonyl chloride, was described. Exemplified compounds I were evaluated for their activity as SOS1 modulators (data given for representative compounds I). Also disclosed are pharmaceutical compositions comprising compounds I. The experimental process involved the reaction of 1-(Tetrahydro-2H-pyran-4-yl)-1H-pyrazole-4-carboxylic acid(cas: 1340372-11-3).Reference of 1-(Tetrahydro-2H-pyran-4-yl)-1H-pyrazole-4-carboxylic acid

The Article related to bicyclic heterocyclyl compound pyrrolopyrimidinamine cyclopentapyrimidinamine pyrimidoazepinamine preparation sos1 modulator, Heterocyclic Compounds (More Than One Hetero Atom): Pyrimidines and Quinazolines and other aspects.Reference of 1-(Tetrahydro-2H-pyran-4-yl)-1H-pyrazole-4-carboxylic acid

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

On April 20, 2017, Nicolaou, Kyriacos C.; Rhoades, Derek; Wang, Yanping; Totokotsopoulos, Sotirios published a patent.Category: pyrazoles-derivatives The title of the patent was Methods of synthesis, methods of treatment with, and drug conjugates of epothilone analogs. And the patent contained the following:

In one aspect, the present disclosure provides epothilone analogs I [wherein: X1 is absent, O or NRa; Ra is H, C≤8-alkyl, C≤8-cycloalkyl,(C≤6-alkyldiyl)-(C≤8-cycloalkyl), or a substituted version of either of these groups; provided that when X1 is absent, that the atoms to which it is attached are a part of a double bond;]. [X2, X3 and X4 are each independently O or NRb; wherein, Rb is H or C≤8-alkyl, C≤8-cycloalkyl, (C≤6-alkanediyl)-(C≤8-cycloalkyl), C≤b-aralkyl, or a substituted version of either of these groups;]. [Y1 and Y2 are each independently NH2, OH, or C≤8-alkoxy, C≤8-aralkoxy, C≤8-acyloxy, (C≤8-alkyl)amino, di(C≤8-alkyl)amino, C≤8-amido, or a substituted version of any of these groups, or ORc, wherein Rc is a hydroxy protecting group;]. [R1, R3, R4, R5, R6 and R7 are each independently H or C≤12-alkyl, C≤12-cycloalkyl, C≤12-alkenyl, C≤12-alkynyl, C≤12-aryl, or a substituted version of any of these groups; and,]. [R2 is C≤12-heteroaryl, C≤8-heteroarenediyl-Rd, or a substituted version of either of these groups; wherein Rd is C≤12-alkyl, C≤12-aryl, C≤12-aralkyl, C≤12-heteroaryl, C≤12-heteroaralkyl, or a substituted version of either of these groups;]. [Provided that R2 is not 2-methylthiazolyl, 2-(hydroxymethyl)thiazolyl, N-2-methyl-3- (methylthio)pyrazolyl or 2-(methylthio)thiazolyl;], or a pharmaceutically acceptable salt thereof. In another aspect, the present disclosure also provides methods of preparing the compounds disclosed herein. In another aspect, the present disclosure also provides pharmaceutical compositions and methods of use of the compounds disclosed herein. Addnl., drug conjugates with cell targeting moieties of the compounds are also provided. Thus, epothilone B pyrazole analog II was prepared and tested for pharmacol. activity [EC50 = 19 μM for induction of tubulin assembly; GI50 = 14 nM vs. MCF-7 cell line; GI50 = 38 nM vs. OVCAR-8 cell line]. The experimental process involved the reaction of 5-Bromo-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole(cas: 1187582-58-6).Category: pyrazoles-derivatives

The Article related to epothilone analogs preparation antitumor, antibody epothilone analog conjugate preparation cancer cell targeting, Biomolecules and Their Synthetic Analogs: Other Bacterial and Fungal Metabolites and other aspects.Category: pyrazoles-derivatives

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

On December 7, 2017, Eriksen, Birgitte Langer; Gustafsson, Magnus; Hougaard, Charlotte; Jacobsen, Thomas Amos; Jefson, Martin R.; Klein, Jessica; Larsen, Janus Schreiber; Lowe, John A., III; McCall, John M.; Strooebaek, Dorte; Von Schoubye, Nadia Lyboel; Keaney, Gregg F. published a patent.Safety of 5-Methoxy-1H-pyrazole The title of the patent was Preparation of cycloalkylamino nitrogen heterocycles as potassium channel modulators for the treatment and prevention of disorders. And the patent contained the following:

The invention relates to preparation of cycloalkylamino nitrogen heterocycles of formula I wherein all the variables are as defined in the disclosure, and pharmaceutically acceptable salts thereof, which are useful for treating a variety of diseases, disorders or conditions which can be affected by potassium channel modulation. Also provided are pharmaceutical compositions comprising the compounds I pharmaceutically acceptable salts thereof, and methods for their use in treating one or more diseases, disorders or conditions, associated with potassium channels. The experimental process involved the reaction of 5-Methoxy-1H-pyrazole(cas: 215610-30-3).Safety of 5-Methoxy-1H-pyrazole

The Article related to cycloalkylamino nitrogen heterocycle potassium channel modulator disease treatment prophylaxis, Heterocyclic Compounds (More Than One Hetero Atom): Pyrimidines and Quinazolines and other aspects.Safety of 5-Methoxy-1H-pyrazole

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