Category: 153597-59-2

On September 30, 1993, Hichour, M.; Mary, F.; Marzin, C.; Naji, M.; Tarrago, G. published an article.Category: pyrazoles-derivatives The title of the article was N-Alkylation of pyrazolones with OH-protection. And the article contained the following:

The synthesis of biheterocyclic compound I containing two pyrazolone sub-units is described. The oxygen atom of 3-carbethoxypyrazol-5-one is first protected with dihydropyran to obtain selective alkylation with 1-3-dibromopropane. 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).Category: pyrazoles-derivatives

The Article related to pyrazolonecarboxylate protection alkylation dibromopropane, Heterocyclic Compounds (More Than One Hetero Atom): Pyrazoles and other aspects.Category: pyrazoles-derivatives

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 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 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

On July 27, 2006, Venkatesan, Aranapakam M.; Agarwal, Atul; Abe, Takao; Ushirogochi, Hideki; Yamamura, Itsuka; Ado, Mihira; Tsuyoshi, Takasaki; Dos Santos, Osvaldo; Gu, Yansong; Sum, Fuk-Wah; Li, Zhong; Francisco, Gerry; Lin, Yang-I.; Petersen, Peter J.; Yang, Youjun; Kumagai, Toshio; Weiss, William J.; Shlaes, David M.; Knox, James R.; Mansour, Tarek S. published an article.COA of Formula: C9H12N2O3 The title of the article was Structure-Activity Relationship of 6-Methylidene Penems Bearing 6,5 Bicyclic Heterocycles as Broad-Spectrum β-Lactamase Inhibitors: Evidence for 1,4-Thiazepine Intermediates with C7 R Stereochemistry by Computational Methods. And the article contained the following:

The design and synthesis of a series of 6-methylidene penems containing [6,5]-fused bicycles (thiophene, imidazole, or pyrazle-fused system) as novel class A, B, and C β-lactamase inhibitors is described. These penems proved to be potent inhibitors of the TEM-1 (class A) and AmpC (class C) β-lactamases and less so against the class B metallo-β-lactamase CcrA. Their in vitro and in vivo activities in combination with piperacillin are discussed. On the basis of the crystallog. structures of a serine-bound reaction intermediate of imidazo[2,1-c]oxazine I with SHV-1 (class A) and GC1 (class C) enzymes, compounds II (R = Q, Q1, Q2, etc.) were designed and synthesized. Penems are proposed to form a seven-membered 1,4 thiazepine ring in both class A and C β-lactamases. The interaction energy calculation for the enzyme-bound intermediates favor the formation of the C7 R enantiomer over the S enantiomer of the 1,4-thiazepine in both β-lactamases, which is consistent with those obtained from the crystal structure of I with SHV-1 and GC1. 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).COA of Formula: C9H12N2O3

The Article related to methylidene penem preparation beta lactamase inhibitor structure activity, bactericide methylidene penem structure activity, Biomolecules and Their Synthetic Analogs: Beta-Lactam Fungal Metabolites and other aspects.COA of Formula: C9H12N2O3

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 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

On July 27, 2006, Venkatesan, Aranapakam M.; Agarwal, Atul; Abe, Takao; Ushirogochi, Hideki; Yamamura, Itsuka; Ado, Mihira; Tsuyoshi, Takasaki; Dos Santos, Osvaldo; Gu, Yansong; Sum, Fuk-Wah; Li, Zhong; Francisco, Gerry; Lin, Yang-I.; Petersen, Peter J.; Yang, Youjun; Kumagai, Toshio; Weiss, William J.; Shlaes, David M.; Knox, James R.; Mansour, Tarek S. published an article.COA of Formula: C9H12N2O3 The title of the article was Structure-Activity Relationship of 6-Methylidene Penems Bearing 6,5 Bicyclic Heterocycles as Broad-Spectrum β-Lactamase Inhibitors: Evidence for 1,4-Thiazepine Intermediates with C7 R Stereochemistry by Computational Methods. And the article contained the following:

The design and synthesis of a series of 6-methylidene penems containing [6,5]-fused bicycles (thiophene, imidazole, or pyrazle-fused system) as novel class A, B, and C β-lactamase inhibitors is described. These penems proved to be potent inhibitors of the TEM-1 (class A) and AmpC (class C) β-lactamases and less so against the class B metallo-β-lactamase CcrA. Their in vitro and in vivo activities in combination with piperacillin are discussed. On the basis of the crystallog. structures of a serine-bound reaction intermediate of imidazo[2,1-c]oxazine I with SHV-1 (class A) and GC1 (class C) enzymes, compounds II (R = Q, Q1, Q2, etc.) were designed and synthesized. Penems are proposed to form a seven-membered 1,4 thiazepine ring in both class A and C β-lactamases. The interaction energy calculation for the enzyme-bound intermediates favor the formation of the C7 R enantiomer over the S enantiomer of the 1,4-thiazepine in both β-lactamases, which is consistent with those obtained from the crystal structure of I with SHV-1 and GC1. 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).COA of Formula: C9H12N2O3

The Article related to methylidene penem preparation beta lactamase inhibitor structure activity, bactericide methylidene penem structure activity, Biomolecules and Their Synthetic Analogs: Beta-Lactam Fungal Metabolites and other aspects.COA of Formula: C9H12N2O3

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