Tag: 100-200

On April 12, 2012, Biggadike, Keith; Birault, Veronique; Champigny, Aurelie Cecile; Coe, Diane Mary; Hughes, Owen Rhys; Needham, Deborah; Tape, Daniel Terence published a patent.Synthetic Route of 143803-93-4 The title of the patent was Imidazo[1,2-a]pyridine and pyrazolo[1,5-a]pyridine derivatives as TRPV1 antagonists and their preparation and use for the treatment of TRPV1-mediated diseases. And the patent contained the following:

The invention relates to imidazopyridine and pyrazolopyridine derivatives of formula I, which are TRPV1 antagonists and which are useful in the treatment of TRPV1-mediated diseases. Compounds of formula I wherein A is single bond, CH2 and CH(CH3); X1 is H, F and Me; X2 is H, F, Me and CH2OH; X3 is H, F and Ch2OH; provided that at least two of X1, X2 and X3 are H; Y is C when Z is N, and Y is N when Z is C; R1 is halo, C1-4 alkyl, CF3 and OCF3; R2 and R3 are independently H, halo, C1-4 alkyl, CF3 and OCF3; and pharmaceutically acceptable salts and solvates, are claimed. Example compound II was prepared by a amidation of imidazo[1,2-a]pyridine-3-carboxylic acid with (2-{[4-(1,1-dimethylethyl)phenyl]oxy}ethyl)amine. All the invention compounds were evaluated for their TRPV1 antagonistic activity. From the assay, it was determined that all compounds exhibited a pIC50 value greater than 5.2. The experimental process involved the reaction of 4-Methylpyrazolo[1,5-a]pyridine-3-carboxylic acid(cas: 143803-93-4).Synthetic Route of 143803-93-4

The Article related to imidazopyridine preparation trpv1 antagonist treatment disease, pyrazolopyridine preparation trpv1 antagonist treatment disease, Heterocyclic Compounds (More Than One Hetero Atom): Imidazoles and other aspects.Synthetic Route of 143803-93-4

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

On January 13, 2022, Barrett, Matthew; Cockerill, George Stuart; Good, James; Avery, Craig Alex; Cochrane, Edward James; Jones, Stefan Paul; Onions, Stuart Thomas; Warner, Andrew Joseph published a patent.Recommanded Product: Ethyl 6,7-dihydro-5H-pyrazolo[5,1-b][1,3]oxazine-2-carboxylate The title of the patent was Synthesis of Benzodiazepines useful in treating a respiratory syncytial virus infection. And the patent contained the following:

The synthesis of benzodiazepines, I, wherein: one of R1 or R2 can be II such that the other group is selected from H, cycloalkyl, halo, amino, benzyl, Ph, 4- to 10-membered heterocyclic or heteroaryl groups; R3 can be H or halo; and the ring A can be a 5- or 6-membered heterocyclic ring system containing a variety of N, O or C atoms are prepared as pharmaceutically acceptable salt RSV inhibitors used to treat or prevent an RSV infection. Of note, II was synthesized and displayed an RSV A2 plaque EC50 of 33 nM and cell cytotoxicity of greater than 25,000 nM CC50 and presented in aqueous formulations. Further, some I derivatives were tested in vitro pharmacokinetics to investigate liver microsomal stability. 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).Recommanded Product: Ethyl 6,7-dihydro-5H-pyrazolo[5,1-b][1,3]oxazine-2-carboxylate

The Article related to benzodiazepine preparation antiviral rsv infection, Heterocyclic Compounds (More Than One Hetero Atom): Diazepines and other aspects.Recommanded Product: Ethyl 6,7-dihydro-5H-pyrazolo[5,1-b][1,3]oxazine-2-carboxylate

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 September 24, 2021, Zhao, Zhiming; Liu, Lifeng; Liu, Qingyun; Wang, Hailong; Guan, Huiping; Da, Chenxiao; Chen, Xi; Xu, Guiliang published a patent.Safety of Ethyl 6,7-dihydro-5H-pyrazolo[5,1-b][1,3]oxazine-2-carboxylate The title of the patent was Polyheterocyclic substituted pyrimidine or pyridylamine derivatives, compositions thereof and medical applications thereof. And the patent contained the following:

The invention discloses the polyheterocyclic substituted pyrimidine or pyridylamine derivatives (e.g., I) as adenosine receptor antagonists, which have significant adenosine A2A receptor and/or adenosine A2B receptor antagonistic activities. For example, 3-(2-amino-6-(1-((5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-2-yl)methyl)-1H-1,2,3-triazol-4-yl)pyrimidin-4-yl)-2-methylbenzonitrile (I) was prepared via reaction of 3-bromo-2-methylbenzonitrile with bis(pinacolato)diboron, followed by Suzuki coupling reaction with 2-amino-4,6-dichloropyrimidine, followed by Sonogashira coupling with (triisopropylsilyl)acetylene, followed by Click reaction with 2-(azidomethyl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole. The title compounds can be used in medicines for treating diseases mediated by adenosine A2A receptor and/or adenosine A2B receptor. 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).Safety of Ethyl 6,7-dihydro-5H-pyrazolo[5,1-b][1,3]oxazine-2-carboxylate

The Article related to pyrimidine pyridylamine triazole adenosine receptor antagonist immunomodulator antitumor, Heterocyclic Compounds (More Than One Hetero Atom): Pyrimidines and Quinazolines and other aspects.Safety of Ethyl 6,7-dihydro-5H-pyrazolo[5,1-b][1,3]oxazine-2-carboxylate

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

On August 18, 2016, Gray, Nathanael S.; Hatcher, John; Choi, Hwan Geun published a patent.Name: 6-Chloro-4-methoxy-1H-pyrazolo[3,4-d]pyrimidine The title of the patent was LRRK2 inhibitors and methods of making and using the same. And the patent contained the following:

The invention relates to compounds of formula I, II, and III as LRRK2 inhibitors; their preparation and use in the treatment of neurodegenerative diseases, such as Parkinson’s disease. Compounds of formula I wherein Rx is NRARB, substituted piperidinylmethanone, substituted morpholinomethanone, etc.; RA and RB are independently (un)substituted C1-6 alkyl and COR7; R7 is (un)substituted C1-6 alkyl, (un)substituted C2-6 alkenyl, (un)substituted C2-6 alkynyl; X1, X2 and X3 are independently N, NH and derivatives, substituted C; Rn is H and (un)substituted C1-6 alkyl; each R1 is independently (un)substituted C1-6 alkyl, (un)substituted C1-6 alkoxy and halo; m = 0 – 3; R2 is H, alkoxy, halo, etc.; and pharmaceutically acceptable salts thereof, are claimed. Example compound IV was prepared by a multistep procedure (procedure given). The invention compounds were evaluated for their LRRK2 inhibitory activity (some data given). The experimental process involved the reaction of 6-Chloro-4-methoxy-1H-pyrazolo[3,4-d]pyrimidine(cas: 98138-75-1).Name: 6-Chloro-4-methoxy-1H-pyrazolo[3,4-d]pyrimidine

The Article related to pyrrolopyrimidine preparation lrrk2 inhibitor treatment neurodegenerative disease, Heterocyclic Compounds (More Than One Hetero Atom): Pyrimidines and Quinazolines and other aspects.Name: 6-Chloro-4-methoxy-1H-pyrazolo[3,4-d]pyrimidine

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

On June 25, 2020, Brenneman, Jehrod Burnett; Krall, Elsa Beyer; Schlabach, Michael; Wylie, Andrew Alistair published a patent.Recommanded Product: 6-Chloro-4-methoxy-1H-pyrazolo[3,4-d]pyrimidine The title of the patent was Preparation of substituted pyrazolopyrimidines and substituted purines and their use as ubiquitin-specific-processing protease 1 (USP1) inhibitors. And the patent contained the following:

The present disclosure provides compounds having formula I and the pharmaceutically acceptable salts and solvates thereof, wherein X1, X2 is independently N and CR2; R1 and R2 are independently H, halo, cyano, (un)substituted alkyl, etc.; R3 is (un)substituted Ph, pyridinyl, pyrazolyl, etc.; X11 and X12 is independently N and CH; R5′ is H, (un)substituted C1-6alkyl, (un)substituted C1-6alkoxy, etc.; R5 is (un)substituted C1-6alkyl, (un)substituted C2-6alkenyl, C1-6haloalkyl, etc.; R6 and R7 is independently H, halo, CN, (un)substituted alkenyl, etc. The present disclosure is also directed to the use of compounds of Formula I to inhibit a USP1 protein and to treat a disorder responsive to the inhibition of USP1 proteins and USP1 activity. Example compound II was prepared via a multistep procedure (procedure given). From the assay, it was determined that example compound II exhibited IC50 value of > 200 nM towards USP1. The experimental process involved the reaction of 6-Chloro-4-methoxy-1H-pyrazolo[3,4-d]pyrimidine(cas: 98138-75-1).Recommanded Product: 6-Chloro-4-methoxy-1H-pyrazolo[3,4-d]pyrimidine

The Article related to pyrazolopyrimidines purine preparation usp1 inhibitor treatment cancer, Heterocyclic Compounds (More Than One Hetero Atom): Pyrimidines and Quinazolines and other aspects.Recommanded Product: 6-Chloro-4-methoxy-1H-pyrazolo[3,4-d]pyrimidine

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

On February 1, 2007, Oslob, Johan D.; Yu, Chul Hyun published a patent.Reference of 1-Methyl-1H-pyrazolo[4,3-d]pyrimidin-7-ol The title of the patent was Pyrazolopyrimidines useful as Aurora kinase inhibitors and their preparation, pharmaceutical compositions and use in the treatment of Aurora kinase mediated diseases. And the patent contained the following:

The invention provides compounds having the formula I, which are useful as inhibitors of protein kinase (e.g., Aurora), and thus are useful, for example, for the treatment of Aurora mediated diseases. Compounds of formula I wherein dotted line is double bond as valency permits; R2 is H, halo, CN, NO2, (hetero)aliphatic, (hetero)alicyclic and (hetero)aromatic moiety; R4 is absent, H, (hetero)aliphatic, (hetero)alicyclic, and (hetero)aromatic moiety; if R4 is absent, X1 and X2 are independently NH and derivatives and CR1 proviso that only one of X1 and X2 are CR1; if R4 is present X1 and X2 are independently N and derivatives, and CR1, proviso that only one of X1 and X2 is CR1; R1 is H, halo, CN, No2, (hetero)aliphatic, etc.; L1 is 2-8 atom heteroaliph. linker; L2 is 1-6 atom heteroaliph. linker; Y is (hetero)alicyclic, and (hetero)aromatic moiety; Z is (hetero)alicyclic, (hetero)aliphatic, and (hetero)aromatic moiety; are claimed. Example compound II was prepared by amination of 4-chloro-5-methylpyrazolopyrimidine derivative with 2-[2-(3-trifluoromethylphenylurido)thiazol-2-yl]ethylamine. All the invention compounds were evaluated for their Aurora kinase inhibitory activity. The experimental process involved the reaction of 1-Methyl-1H-pyrazolo[4,3-d]pyrimidin-7-ol(cas: 314021-93-7).Reference of 1-Methyl-1H-pyrazolo[4,3-d]pyrimidin-7-ol

The Article related to pyrazolo pyrimidine preparation aurora kinase inhibitor, Heterocyclic Compounds (More Than One Hetero Atom): Pyrimidines and Quinazolines and other aspects.Reference of 1-Methyl-1H-pyrazolo[4,3-d]pyrimidin-7-ol

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

On July 8, 2004, Abe, Takao; Matsunaga, Hiroshi; Mihira, Ado; Sato, Chisato; Ushirogochi, Hideki; Sato, Koichi; Takasaki, Tsuyoshi; Venkatesan, Aranapakam Mudumbai; Mansour, Tarek Suhayl published a patent.Product Details of 153597-59-2 The title of the patent was Process for preparing 6-alkylidene penem derivatives. And the patent contained the following:

The present invention provides a process of making compounds of formula I (R = H, C1-6 alkyl, C5-6 cycloalkyl, or substituted ester; A, B = H, heteroaryl, fused bicycles, fused tricycles, etc.) which are useful for the treatment of bacterial infection or disease. Thus, sodium (5R),(6Z)-6-(2,3-dihydroimidazo[2,1-b]thiazol-6-ylmethylene)penem-3-carboxylate (II) was prepared via a multistep synthetic sequence which started from 6-aminopenicillanic acid. 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).Product Details of 153597-59-2

The Article related to alkylidene penem derivative antibacterial preparation, Biomolecules and Their Synthetic Analogs: Other Bacterial and Fungal Metabolites and other aspects.Product Details of 153597-59-2

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

On November 13, 2003, Venkatesan, Aranapakam Mudumbai; Mansour, Tarek Suhayl; Abe, Takao; Yamamura, Itsuki; Takasaki, Tsuyoshi; Agarwal, Atul; Dos Santos, Osvaldo; Sum, Fuk-Wah; Lin, Yang-I. published a patent.Name: Ethyl 6,7-dihydro-5H-pyrazolo[5,1-b][1,3]oxazine-2-carboxylate The title of the patent was Preparation of bicyclic 6-alkylidene-penems as β-lactamase inhibitors for use against bacterial infections or diseases. And the patent contained the following:

The present invention provides bicyclic 6-alkylidene-penems (shown as I; variables defined below; e.g. II), pharmaceutical compositions and the use thereof for the treatment of bacterial infection or disease in a patient in need thereof. IC50 values for inhibition of β-lactamase from 4 sources are tabulated for >30 examples of I; in vitro minimal inhibitory concentrations against 9 types of bacteria are tabulated for >30 examples of I; ED50 values for protective effects of >30 examples of I (sometimes combined with piperacillin) in mice are tabulated. For I: one of A and B is H and the other is an (un)substituted fused bicyclic heteroaryl group; X is O or S; R5 is H, C1-C6 alkyl, C5-C6 cycloalkyl, or CHR3OCOC1-C6alkyl; and R3 is H, C1-C6 alkyl, C5-C6 cycloalkyl, (un)substituted aryl, or (un)substituted heteroaryl. The compounds I when combined with β-lactam antibiotics will provide an effective treatment against life threatening bacterial infections. Forty example preparations of I are included. For example, II was prepared in 5 steps (25, 91, 76, 40, 18 % yields, resp.) starting from 1-benzoyl-4-piperidone and Et mercaptoacetate and involving intermediates Et 5-benzoyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2-carboxylate, (5-benzyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl)methanol, 2-formyl-5-benzyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridine and 4-nitrobenzyl 6-[(acetyloxy)(5-benzyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl)methyl]-6-bromo-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate. 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).Name: Ethyl 6,7-dihydro-5H-pyrazolo[5,1-b][1,3]oxazine-2-carboxylate

The Article related to bicyclic alkylidene penem beta lactamase inhibitor antibacterial, beta lactam antibiotic codrug bicyclic alkylidene penem preparation, Heterocyclic Compounds (More Than One Hetero Atom): Thiazoles, Isothiazoles and other aspects.Name: Ethyl 6,7-dihydro-5H-pyrazolo[5,1-b][1,3]oxazine-2-carboxylate

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