Category: naphthyridine

On October 6, 2008, Harris, Craig S.; Germain, Herve; Pasquet, Georges published an article.Quality Control of tert-Butyl 7-(2-hydroxyethyl)-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxylate The title of the article was Facile preparation of thiophene C2-ethers using the Mitsunobu reaction. And the article contained the following:

The preparation of thiophene ethers generally requires forcing conditions thus limiting the choice of alkyl substituent. Herein, we report the first successful generally applicable conditions for the selective O-alkylation of 2(5H)-thiophenone. The experimental process involved the reaction of tert-Butyl 7-(2-hydroxyethyl)-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxylate(cas: 445490-78-8).Quality Control of tert-Butyl 7-(2-hydroxyethyl)-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxylate

The Article related to thiophenone alc mitsunobu alkylation, thiophene ether preparation, Heterocyclic Compounds (One Hetero Atom): Thiophenes and other aspects.Quality Control of tert-Butyl 7-(2-hydroxyethyl)-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxylate

Referemce:
1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – PubChem

On May 20, 2010, Shipps, Gerald W., Jr.; Cheng, Cliff C.; Achab, Abdelghani Abe; Yao, Zhiping; Whitehurst, Charles E.; Zhang, Mingxuan; Yang, Xianshu; Herr, Robert Jason; Zych, Andrew John; Roy, Sudipta; Yang, Jinhai published a patent.Electric Literature of 445490-78-8 The title of the patent was Preparation of benzyltetrahydronaphthyridinylethylurea derivatives and analogs for use as HIV blockers. And the patent contained the following:

Title compounds I [L = (un)substituted urea, isothiourea, sulfamide, etc.; R1 = (un)substituted tetrahydronaphthalene, tetrahydronaphthyridine, dihydrobenzothio pyran; each R2 independently = H, (un)substituted alkyl, or cycloalkyl; each R3 independently = H, (un)substituted alkyl, cycloalkyl, or aryl; R4 = (un)substituted aryl, cycloalkyl, or heteroaryl ring containing 1 to 3 heteroatoms selected from O, S, or N; m = 1 to 3; n = 0 to 2], and their pharmaceutically acceptable salts, are prepared and disclosed as HIV blockers. Thus, e.g., II was prepared by coupling of 3,4-dichlorobenzyl isocyanate with 2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethanamine hydrochloride. Select I were evaluated in HIV CXCR4 affinity assays, e.g., II demonstrated an IC50 value of 2.4 μM. The experimental process involved the reaction of tert-Butyl 7-(2-hydroxyethyl)-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxylate(cas: 445490-78-8).Electric Literature of 445490-78-8

The Article related to naphthyridinylethylurea benzyltetrahydro derivative preparation hiv blocker, benzyltetrahydronaphthyridinylethylurea analog preparation hiv blocker, Heterocyclic Compounds (One Hetero Atom): Pyridines and other aspects.Electric Literature of 445490-78-8

Referemce:
1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – PubChem

On December 13, 2007, Arnould, Jean-Claude; Delouvrie, Benedicte; Ducray, Richard; Lambert-Van Der Brempt, Christine Marie Paul published a patent.COA of Formula: C15H22N2O3 The title of the patent was Preparation of tyrosine derivatives, especially N-(benzoyl)-O-[2-[(pyridin-2-yl)amino]ethyl]-L-tyrosines and related compounds, as α5β1 integrin antagonists for treating solid tumors. And the patent contained the following:

The invention is related to tyrosine derivatives I [Xa = O, S; R1 = Br, Cl, cyclopentylmethyl, C1-3 alkyl, etc.; R2, each R3 = independently H, halo, CN, OH, NH2, (un)substituted alk(en/yn)yl, alkanoylamino, N-alkylsulfamoyl, etc.; or R2R3 = C1-3 alkylenedioxy; m = 0-3; R4 = H, (un)substituted heterocyclyl, heteroaryl, etc.; A = Ph, pyridinyl, thiophenyl; n = 0-4; each R5 = independently halo, OH, SH, carbamoyl, sulfamoyl, alkylsulfonyl, alkynoylamino, etc.; or 2 R5’s optionally form a C1-3 alkylenedioxy; X = a bond, O, S, SO, SO2, CO, (un)substituted CH:CH, etc.; Y = (un)substituted alkylene, cycloalk(en)ylene, heterocyclyl; Z = a bond, O, S, (un)substituted alkylene, CC, etc.;] and their pharmaceutically acceptable salts and prodrugs, to processes for preparing them, and to pharmaceutical compositions containing them for use as α5β1 integrin antagonists in the treatment in warm-blooded animals such as humans of diseases that have a significant angiogenesis or vascular component such as for treatment of solid tumors. The invention is also related to α5β1 antagonists that also exhibit appropriate selectivity profile(s) against other integrins. Thus, etherification of tert-Bu 7-(2-hydroxyethyl)-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxylate with Me N-(2,6-dichlorobenzoyl)-L-tyrosinate (preparation given), cleavage of the tert-butoxycarbonyl group and saponification of the Me ester gave tyrosine derivative II. The effects of compounds I as α5β1 integrin inhibitors were tested (e.g., the invention compound II had IC50 values of 0.0004 μM in a binding assay and 0.002 μM in an adhesion assay). The experimental process involved the reaction of tert-Butyl 7-(2-hydroxyethyl)-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxylate(cas: 445490-78-8).COA of Formula: C15H22N2O3

The Article related to tyrosine preparation alpha5beta1 integrin antagonist solid tumor, antitumor benzoyl pyridinylaminoethyl tyrosine derivative preparation alpha5beta1 integrin antagonist, Amino Acids, Peptides, and Proteins: Amino Acids and other aspects.COA of Formula: C15H22N2O3

Referemce:
1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – PubChem

On March 15, 2018, Jiang, Lan; Morgans, David John; Bergne, Gustave; Chen, Chun; Li, Hui; Andre, Patrick; Halcomb, Randall Lynn; Cha, Jacob; Hom, Timothy published a patent.Category: naphthyridine The title of the patent was Preparation of N-acyl amino acid compounds as αvβ1 integrin inhibitors for treating tissue specific fibrosis. And the patent contained the following:

The invention is related to the preparation of compounds R1CONHCH(CO2H)CH2ALR2 [R1 = (un)substituted C6-14 aryl or C5-10-membered heteroaryl; R2 = (un)substituted 5- to 10-membered heteroaryl containing at least 2 ring N’s, 3- to 12-membered heterocyclyl containing at least 2 ring N’s, NHR3, etc.; R3 =(un)substituted 5- to 10-membered heteroaryl containing at least 1 ring N, or 3- to 12-membered heterocyclyl containing at least 1 ring N, wherein the 5- to 10- membered heteroaryl and 3- to 12-membered heterocyclyl; -A-L- = -A1-L1-,-A2-L2-, A3; A1 = (un)substituted C3-8 cycloalkyiene, C3-8 cycloalkenylene, C6-14 arylene, 5- to 10-membered heteroarylene or 3- to 12-membered heterocyclylene; A2 = = (un)substituted C3-8 cycloalkyiene, C3-8 cycloalkenylene; A3 = = (un)substituted C5-10 cycloalkyiene, C5-10 cycloalkenylene; L1 = OZ, (un)substituted saturated 3- to 4-membered heterocyclylene, OZX1, etc.; Z = CR5aR5b; R5a, R5b = independently H, C1-6 alkyl; X1 = (un)substituted C1-6 alkylene or C2-6 alkenylene; with the exception of specified compounds], e.g., I, that are αvβ1 integrin inhibitors, pharmaceutical compositions containing them and for treating tissue specific fibrosis. Thus, I was prepared by a multi-step synthesis starting from 2-aminonicotinaldehyde and Et 4-oxopentanoate using Me (2S)-2-[(benzyloxycarbonyl)amino]-3-(4-hydroxyphenyl)propanoate and benzoic acid. The compounds of the invention were tested for αvβ1 integrin inhibition in a cell adhesion assay and in a solid phase integrin αvβ1 binding assay. The experimental process involved the reaction of tert-Butyl 7-(2-hydroxyethyl)-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxylate(cas: 445490-78-8).Category: naphthyridine

The Article related to acyl amino acid alpha v beta 1 integrin inhibitor, preparation acyl amino acid tissue specific fibrosis, Amino Acids, Peptides, and Proteins: Amino Acids and other aspects.Category: naphthyridine

Referemce:
1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – PubChem

On March 31, 2007, Raboisson, Pierre; DesJarlais, Renee L.; Reed, Rolanda; Lattanze, Jennifer; Chaikin, Margery; Manthey, Carl L.; Tomczuk, Bruce E.; Marugan, Juan Jose published an article.Related Products of 445490-78-8 The title of the article was Identification of novel short chain 4-substituted indoles as potent αvβ3 antagonist using structure-based drug design. And the article contained the following:

The vitronectin receptor αvβ3 has been identified as a promising potential target for the treatment of osteoporosis, diabetic retinopathy and cancer. The authors have recently reported 5-substituted indoles 3-[5-[2-(5,6,7,8-tetrahydro[1,8]naphthyridin-2-yl)ethoxy]indol-1-yl]-3-(3-pyridyl)propionic acid 3 and 3-[5-[2-(5,6,7,8-tetrahydro[1,8]naphthyridin-2-yl)ethoxy]indol-1-yl]-3-(3,4-methylenedioxyphenyl)propionic acid 4, as an original series of potent αvβ3 antagonists with subnanomolar activity. Ligand-protein docking analyses have been performed to generate binding models of three different chem. classes of known αvβ3 antagonists with αvβ3. Results of this docking study suggested that indoles bearing the basic tetrahydronaphthyridine group at position 4 can easily adopt the correct binding conformation and should be as potent as our current 5-substituted indole leads 3 and 4. This hypothesis was nicely demonstrated by the synthesis of a series of 1,4-disubstituted indoles through a tandem of reactions involving: (i) the N-alkylation of indoles 15 and 22 with propargyl esters and cesium fluoride, and (ii) a Heck coupling reaction between 4-bromoindole and 7-vinyl-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid tert-Bu ester 12, or (iii) a reductive amination involving the N-substituted-4-aminoindole 23 and the BOC-protected tetrahydro[1,8]naphthyridine aldehyde 13. Among the compounds assayed, compound (I) showed the most promising activity on αvβ3 (IC50 = 0.5 nM), and was found to have the same potency as our current leads 3 and 4, while maintaining selectivity over αIIbβIIIa. Moreover, based on the reasonable apparent permeability coefficient in an in vitro CACO-2 cell monolayer assay (Papp apical/basolateral = 2.2 × 10-6 cm/s, Papp basolateral/apical = 2.5 × 10-6 cm/s), I is expected to be absorbed through the intestine in human. Thus, 1,4-disubstituted indole I represents a new lead for this novel class of conformationally restricted αvβ3 antagonists. Addnl., this study validates the pharmacophore model previously postulated and provides an improved basis for further structure-based drug design in the field of αvβ3. The experimental process involved the reaction of tert-Butyl 7-(2-hydroxyethyl)-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxylate(cas: 445490-78-8).Related Products of 445490-78-8

The Article related to pyridylterahydronaphthyridinylethylindol propionate preparation structure integrin antagonist, Pharmacology: Structure-Activity and other aspects.Related Products of 445490-78-8

Referemce:
1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – PubChem

On October 10, 2019, Anderson, Niall A.; Campos, Sebastien; Butler, Sharon; Copley, Royston C. B.; Duncan, Ian; Harrison, Stephen; Le, Joelle; Maghames, Rosemary; Pastor-Garcia, Aleix; Pritchard, John M.; Rowedder, James E.; Smith, Claire E.; Thomas, Jack; Vitulli, Giovanni; Macdonald, Simon J. F. published an article.Formula: C15H22N2O3 The title of the article was Discovery of an Orally Bioavailable Pan αv Integrin Inhibitor for Idiopathic Pulmonary Fibrosis. And the article contained the following:

The heterodimeric transmembrane αv integrin receptors have recently emerged as potential targets for the treatment of idiopathic pulmonary fibrosis. Herein, we describe how subtle modifications of the central aromatic ring of a series of phenylbutyrate-based antagonists of the vitronectin receptors αvβ3 and αvβ5 significantly change the biol. activities against αvβ6 and αvβ8. This resulted in the discovery of a pan αv antagonist (compound 39, 4-40 nM for the integrin receptors named above) possessing excellent oral pharmacokinetic properties in rats (with a clearance of 7.6 mL/(min kg) and a bioavailability of 97%). The experimental process involved the reaction of tert-Butyl 7-(2-hydroxyethyl)-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxylate(cas: 445490-78-8).Formula: C15H22N2O3

The Article related to phenylbutyrate derivative preparation oral integrin inhibitor idiopathic pulmonary fibrosis, Pharmacology: Structure-Activity and other aspects.Formula: C15H22N2O3

Referemce:
1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – PubChem

On February 29, 2000, Nishijima, Kazumi; Nishida, Hidemitsu; Yamashita, Yoshiaki; Ito, Manabu; Onuki, Yoshiaki; Mizota, Masahiro; Miyano, Sotaro published an article.Electric Literature of 76629-10-2 The title of the article was Synthesis and diuretic activity of bicyclic fused heterocycles containing oxime-O-sulfonic acid moiety. And the article contained the following:

In order to investigate the origin of the loop-type diuretic activity of M17055, several variants were designed and synthesized by modifying the quinolinone skeleton, and their diuretic activities were compared with the lead M17055 and furosemide in dogs. It was found that the neg. charge distribution pattern afforded by the dispositional arrangement of the 4-oxime-O-sulfonic acid and 1-N-acyl carbonyl moiety attached to the tetrahydropyridine ring system is inevitable for the development of the activity, which strongly supports the previously proposed model for the active site of the Na+-K+-2Cl- cotransporter. The experimental process involved the reaction of 7-Chloro-2,3-dihydro-1,8-naphthyridin-4(1H)-one(cas: 76629-10-2).Electric Literature of 76629-10-2

The Article related to oxime sulfonate heterocycle preparation diuretic structure, Pharmacology: Structure-Activity and other aspects.Electric Literature of 76629-10-2

Referemce:
1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – PubChem

On October 27, 2016, Asano, Yasutomi; Kojima, Takuto; Kurasawa, Osamu; Wong, Tzu-Tshin; Hirata, Yasuhiro; Iwamura, Naoki; Saito, Bunnai; Tanaka, Yuta; Arai, Ryosuke; Imamura, Shinichi; Yonemori, Kazuko; Miyamoto, Yasufumi; Kitamura, Shuji; Sano, Osamu published a patent.Recommanded Product: 7-Chloro-2,3-dihydro-1,8-naphthyridin-4(1H)-one The title of the patent was Preparation of 1-acyl-4-acylaminopiperidine derivatives as serine palmitoyltransferase (SPT) inhibitors. And the patent contained the following:

The present invention relates to the title compounds I [ring Ar = each (un)substituted aromatic heterocyclyl or C6-14 aromatic hydrocarbyl; ring A = each (un)substituted C6-14 aromatic hydrocarbyl or heterocyclyl; R1 = each (un)substituted C6-14 aryl, C3-10 cycloalkyl, or heterocyclyl; when R1 is (un)substituted heterocyclyl, R1 = Q or Q1; ring B = (un)substituted heterocyclyl; ring D = (un)substituted N-containing heterocyclyl; R2 = H or R1 and R2 are bonded together to form (un)substituted 5- or 6-membered aromatic heterocyclyl or (un)substituted benzene ring] or salts thereof. These compounds are serine palmitoyltransferase (SPT) inhibitors and potentially useful for treating or preventing SPT-related disease including congenital disease accompanied by sphingolipid accumulation, cancer, and Niemann-Pick disease in mammals. Thus, 188 mg 2-chlorobenzoyl chloride was gradually added to a solution of 283 mg (7-amino-2-methyl-2,5,6,7-tetrahydro-4H-pyrazolo[4,3-b]pyridin-4-yl)(3,4-dimethoxyphenyl)methanone and 270 mg Et3N in 5 mL CH2Cl2 under ice-cooling and the resulting mixture was stirred at room temperature for 1 h to give, after workup and silica gel chromatog., 2-chloro-N-(4-(3,4-dimethoxybenzoyl)-2-methyl-4,5,6,7-tetrahydro-2H-pyrazolo[4,3-b]pyridin-7-yl)benzamide (II). II at 1 μM inhibited 91% human serine palmitoyltransferase (SPT). A capsule and a tablet formulation containing II were described. The experimental process involved the reaction of 7-Chloro-2,3-dihydro-1,8-naphthyridin-4(1H)-one(cas: 76629-10-2).Recommanded Product: 7-Chloro-2,3-dihydro-1,8-naphthyridin-4(1H)-one

The Article related to acylaminoacylpiperidine preparation serine palmitoyltransferase spt inhibitor, pyrazolopyridinylbenzamide preparation serine palmitoyltransferase spt inhibitor, congenital disease sphingolipid accumulation treatment prevention acylaminoacylpiperidine preparation, cancer niemann pick disease treatment prevention acylaminoacylpiperidine preparation and other aspects.Recommanded Product: 7-Chloro-2,3-dihydro-1,8-naphthyridin-4(1H)-one

Referemce:
1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – PubChem

On July 31, 2006, Raboisson, Pierre; Manthey, Carl L.; Chaikin, Margery; Lattanze, Jennifer; Crysler, Carl; Leonard, Kristi; Pan, Wenxi; Tomczuk, Bruce E.; Marugan, Juan Jose published an article.Application of 445490-78-8 The title of the article was Novel potent and selective αvβ3/αvβ5 integrin dual antagonists with reduced binding affinity for human serum albumin. And the article contained the following:

Pyridopyridineethoxy- and pyridopyridinepropyl-substituted indolepropanoic acids, a pyridineaminopropoxydihydroindoleacetic acid, and a substituted oxopyrrolopyrimidinepropanoic acid are prepared as potential selective dual αvβ3 and αvβ5 integrin receptor antagonists with decreased binding to human serum albumin (HSA). Ammonium tetrahydronaphthyridinylethoxyindolepropanoate I•NH3 is the most effective of the compounds prepared, with subnanomolar affinity for both αvβ3 and αvβ5 (IC50 = 0.29 and 0.16 nM, resp.), low HSA protein binding (40% bound, Kd = 1.1 ± 0.4 × 103 μM), and improved in vitro stability toward human and mouse microsomes (99.9% and 98.7% remaining after 10 min) over previously prepared integrin receptor antagonists. The selectivities of I•NH3 toward α5β1 and IIbIIIa integrins is comparable to those of the initial lead integrin receptor antagonists. The experimental process involved the reaction of tert-Butyl 7-(2-hydroxyethyl)-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxylate(cas: 445490-78-8).Application of 445490-78-8

The Article related to pyridopyridineethoxy indolepropanoic acid preparation integrin receptor antagonist, pyridopyridinepropyl indolepropanoic acid preparation integrin receptor antagonist, oxopyrrolopyrimidinepropanoic acid pyridopyridineethoxy preparation integrin receptor antagonist and other aspects.Application of 445490-78-8

Referemce:
1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – PubChem

On August 31, 1990, Ferrarini, P. L.; Mori, C.; Primofiore, G.; Da Settimo, A.; Breschi, M. C.; Martinotti, E.; Nieri, P.; Ciucci, M. A. published an article.Related Products of 76629-10-2 The title of the article was Synthesis and β-blocking activity of (E)- and (Z)-iminoethers of 1,8-naphthyridine. Potential antihypertensive agents. 4. And the article contained the following:

A series of (E)- (I, R = Br, Cl, Me, OMe or OEt, R1 = H or Br; R2 = iso-Pr, tert-Bu) and (Z)-imino ethers (II, R = Br, Cl, Me, OMe or OEt and R2 = iso-Pr or tert-Bu) of 1,8-naphthyridine were prepared from the corresponding ketones by a series of reactions involving oxime formation, reaction with epichlorohydrin followed by reaction with amines. The pharmacol. activities of these compounds were evaluated by using isolated guinea pig atria or trachea, or rat vas deferens. All compounds showed β2 adrenergic agonist and B1-blocking properties. Neither stimulation nor blocking activity was observed on α receptors. The activity was independent of the side-chain and no difference was observed in activity between (E)-I or (Z)-II. The experimental process involved the reaction of 7-Chloro-2,3-dihydro-1,8-naphthyridin-4(1H)-one(cas: 76629-10-2).Related Products of 76629-10-2

The Article related to beta blocker naphthyridine imino ether preparation, adrenergic agonist naphthyridine imino ether preparation, naphthyridine imino ether adrenergic agonist antagonist, antihypertensive naphthyridine imino ether and other aspects.Related Products of 76629-10-2

Referemce:
1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – PubChem