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Benzoxazole and benzothiazole amides as novel pharmacokinetic enhancers of HIV protease inhibitors

A new class of benzoxazole and benzothiazole amide derivatives exhibiting potent CYP3A4 inhibiting properties was identified. Extensive lead optimization was aimed at improving the CYP3A4 inhibitory properties as well as overall ADME profile of these amide derivatives. This led to the identification of thiazol-5-ylmethyl (2S,3R)-4-(2-(ethyl(methyl)amino)-N-isobutylbenzo[d]oxazole- 6-carboxamido)-3-hydroxy-1-phenylbutan-2-ylcarbamate (C1) as a lead candidate for this class. This compound together with structurally similar analogues demonstrated excellent ‘boosting’ properties when tested in dogs. These findings warrant further evaluation of their properties in an effort to identify valuable alternatives to Ritonavir as pharmacokinetic enhancers.

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Reference£º
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

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Discovery and Pharmacology of a Novel Somatostatin Subtype 5 (SSTR5) Antagonist: Synergy with DPP-4 Inhibition

We report new SSTR5 antagonists with enhanced potency, subtype selectivity, and minimal off-target activities as compared to previously reported compounds. Starting from the reported SSTR5 antagonist 1, we systematically surveyed changes in the central core and head piece while maintaining the diphenyl tail group constant. From this study the azaspirodecanone 10 emerged as a new highly potent and selective SSTR5 antagonist. Compound 10 lowered glucose excursion by 94% in an oral glucose tolerance test (OGTT) in mice following a 3 mg/kg oral dose. The compound increased both total and active circulating incretin hormone GLP-1 levels in mice at a dose of 10 mg/kg. A synergistic effect was also demonstrated when compound 10 was coadministered with a DPP-4 inhibitor, substantially increasing circulating active GLP-1[7-36] amide and insulin in response to a glucose challenge.

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Reference£º
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

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Synthesis and evaluation of arylaminoethyl amides as noncovalent inhibitors of cathepsin S. Part 3: Heterocyclic P3

A series of Nalpha-2-benzoxazolyl-alpha-amino acid-(arylaminoethyl)amides were identified as potent, selective, and noncovalent inhibitors of cathepsin S. Structure-activity relationships including strategies for modulating the selectivities among cathepsins S, K, and L, and in vivo pharmacokinetics are discussed. A X-ray structure of compound 3 bound to the active site of cathepsin S is also reported.

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Reference£º
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

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AMIDE COMPOUNDS AS BOOSTERS OF ANTIVIRALS

The present invention relates to compounds that have CYP450 inhibiting properties and are therefore useful as boosters of certain drugs, i.e. they are able to increase at least one of the pharmacokinetic variables of certain drugs when co-administered. The invention further provides the use of said compounds as improvers of the bioavailability of certain drugs. Methods for the preparation of the compounds of the invention and pharmaceutical compositions are also provided.

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Reference£º
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

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72752-81-9, Methyl 2-mercaptobenzo[d]oxazole-6-carboxylate is a benzoxazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

72752-81-9, To a suspension of this pink solid (320 g, 1.53 mol) and K2CO3 (276 g, 2 mol) in EtOAc (3L) was added MeI (238.9g, 1.68 mol) below 20C. The mixture was stirred at room temperature for 12 hours. TLC (EtOAc/petroleum ether = 1:3) indicated the reaction was complete. Water (2L) was added to the mixture. The organic phase was separated, dried over Na2SO4 and concentrated to give 13 (320 g, 93.8%) as a pink solid.

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Reference£º
Article; Jonckers, Tim H.M.; Rouan, Marie-Claude; Hache, Geerwin; Schepens, Wim; Hallenberger, Sabine; Baumeister, Judith; Sasaki, Jennifer C.; Bioorganic and Medicinal Chemistry Letters; vol. 22; 15; (2012); p. 4998 – 5002;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.72752-81-9,Methyl 2-mercaptobenzo[d]oxazole-6-carboxylate,as a common compound, the synthetic route is as follows.

72752-81-9, Methyl 2-chloro-l,3-benzoxazole-6-carboxylate (Intermediate B) To Compound4 (2 g, 9.5 mmol), SOCl2 (9.8 ml, 134 mmol) and DMF (0.8 niL, 10 mmol) was added at room temperature. The reaction mixture heated to reflux for 15 min. The solvent was removed under reduced pressure. The crude oil was azeotroped with xylene twice. The residue was dissolved in a minimum amount of DCM / MeOH, and then loaded onto a silica gel column, eluting with EtOAc/isohexane to give intermediate B as a white solid. H NMR (500MHz, CDC13, ppm): 4.0 (s, 3H)5 7.8 (d, IH), 8.1 (d, IH), 8.3 (s, IH). LC-MS, M+l – 212.1

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Reference£º
Patent; MERCK SHARP & DOHME CORP.; HE, Jiafang; BAWIEC, John; LIU, Weiguo; LIANG, Gui-Bai; YANG, Lihu; WO2010/56717; (2010); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

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To a suspension of compound 5.3 (320 g, 1.53 mol) and K2CO3 (276 g, 2 mol) in EtOAC (3 L) was added MeI (238.9 g, 1.68 mol) below 20 C. The mixture was stirred at room temperature for 12 hours. TLC (EtOAc/petroleum ether=1:3) indicated the reaction was complete. Water (2 L) was added to the mixture. The organic phase was separated, dried over Na2SO4 and concentrated to give 5.4 (320 g, 93.8%) as a pink solid.

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Reference£º
Patent; TIBOTEC BVBA; US2010/305073; (2010); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

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72752-81-9, Methyl 2-mercaptobenzo[d]oxazole-6-carboxylate is a benzoxazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

72752-81-9, To a suspension of Compound 2a (1 g, 4.78 mmol) in thionyl dichloride (5 mL) was added DMF (0.1 mL). The resulting solution was stirred for 15 min at 80C. The reaction solution was (0261) concentrated under vacuum. The crude was diluted with DCM and washed successively with saturated NaHC03 solution, water and brine. The residue was concentrated under vacuum after dried over anhydrous sodium sulfate. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (23 :77). This resulted in 520 mg (51%) of the title compound as a white solid.

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Reference£º
Patent; HEPAGENE THERAPEUTICS, INC.; XU, Xiaodong; (104 pag.)WO2018/85148; (2018); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

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Methyl 2-mercaptobenzo[d]oxazole-6-carboxylate, cas is 72752-81-9, it is a common heterocyclic compound, the benzoxazole compound, its synthesis route is as follows.,72752-81-9

Methyl 2-chloro-l,3-benzoxazole-6-carboxylate (Intermediate B) To Compound4 (2 g, 9.5 mmol), SOCl2 (9.8 ml, 134 mmol) and DMF (0.8 niL, 10 mmol) was added at room temperature. The reaction mixture heated to reflux for 15 min. The solvent was removed under reduced pressure. The crude oil was azeotroped with xylene twice. The residue was dissolved in a minimum amount of DCM / MeOH, and then loaded onto a silica gel column, eluting with EtOAc/isohexane to give intermediate B as a white solid. H NMR (500MHz, CDC13, ppm): 4.0 (s, 3H)5 7.8 (d, IH), 8.1 (d, IH), 8.3 (s, IH). LC-MS, M+l – 212.1

With the rapid development of chemical substances, we look forward to future research findings about 72752-81-9

Reference£º
Patent; MERCK SHARP & DOHME CORP.; HE, Jiafang; BAWIEC, John; LIU, Weiguo; LIANG, Gui-Bai; YANG, Lihu; WO2010/56717; (2010); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

Downstream synthetic route of Methyl 2-mercaptobenzo[d]oxazole-6-carboxylate

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As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO393,mainly used in chemical industry, its synthesis route is as follows.,72752-81-9

To a suspension of this pink solid (320 g, 1.53 mol) and K2CO3 (276 g, 2 mol) in EtOAc (3L) was added MeI (238.9g, 1.68 mol) below 20C. The mixture was stirred at room temperature for 12 hours. TLC (EtOAc/petroleum ether = 1:3) indicated the reaction was complete. Water (2L) was added to the mixture. The organic phase was separated, dried over Na2SO4 and concentrated to give 13 (320 g, 93.8%) as a pink solid.

With the synthetic route has been constantly updated, we look forward to future research findings about Methyl 2-mercaptobenzo[d]oxazole-6-carboxylate,belong benzoxazole compound

Reference£º
Article; Jonckers, Tim H.M.; Rouan, Marie-Claude; Hache, Geerwin; Schepens, Wim; Hallenberger, Sabine; Baumeister, Judith; Sasaki, Jennifer C.; Bioorganic and Medicinal Chemistry Letters; vol. 22; 15; (2012); p. 4998 – 5002;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem