Heterocyclic Building Blocks-Naphthyridine

On November 16, 2005, Strang, Ross Sinclair; Lunn, Graham; Mathias, John Paul published a patent.Formula: C15H16N2O The title of the patent was Preparation of tetrahydronaphthyridines as histamine H3 receptor ligands. And the patent contained the following:

The title compounds I or II [R1 = (un)substituted Het1; A = (CH2)mNR7R8 (wherein m = 2-6; R7, R8 = H, alkyl, cycloalkyl, hydroxyalkyl or (un)substituted NR7R8 = 4-7 membered saturated heterocyclyl optionally containing more heteroatoms), III (p = 0-2; Q = (un)substituted 4-6 membered saturated heterocyclyl); Het1 = monocyclic or bicyclic heteroaryl having 5-10 ring members which contain 1-4 heteroatoms selected from N, O ans S] which are H3 ligands and are useful in numerous diseases, disorders and conditions, in particular inflammatory, allergic and respiratory diseases, disorders and conditions, were prepared Thus, reacting 2-(3-pyrrolidin-1-ylpropoxy)-5,6,7,8-tetrahydro-1,6-naphthyridine (preparation given) with 2-bromopyrimidine afforded 24% IV. The exemplified compounds I and II have been tested in the H3 assays and were found to have a Ki value of less than 1000 nM in the H3 cell based functional assay. The most preferred examples have a Ki value of less than 30 nM in the H3 cell based functional assay and a Ki value of greater than 4500 nM in the dofetilide binding assay. The pharmaceutical compositions comprising the compounds I or II alone or in combination with other pharmacol. active agent are disclosed. The experimental process involved the reaction of 7-Benzyl-5,6,7,8-tetrahydro-1,7-naphthyridin-2(1H)-one(cas: 869640-41-5).Formula: C15H16N2O

The Article related to naphthyridine preparation histamine h3 receptor ligand, Heterocyclic Compounds (More Than One Hetero Atom): Fused-Ring Systems With Two Or More Hetero Atoms, No More Than One Hetero Atom Per Ring and other aspects.Formula: C15H16N2O

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

On August 31, 1981, Ferrarini, Pier Luigi; Biagi, Giuliana; Livi, Oreste; Primofiore, Giampaolo; Carpene, Marino published an article.Quality Control of 7-Chloro-2,3-dihydro-1,8-naphthyridin-4(1H)-one The title of the article was Synthesis of some 3-substituted [1,8]Naphthyrido[3,2-c][1,8]naphthyridines. A new heterocyclic ring system. And the article contained the following:

The title compounds (I; R = Me, Br, Cl, EtO, HS) were prepared by condensation of naphthyridinones (II) with 2-aminonicotinaldehyde. I were transformed into the fully aromatic compounds by refluxing with nitrobenzene. The experimental process involved the reaction of 7-Chloro-2,3-dihydro-1,8-naphthyridin-4(1H)-one(cas: 76629-10-2).Quality Control of 7-Chloro-2,3-dihydro-1,8-naphthyridin-4(1H)-one

The Article related to naphthyridonaphthyridine, condensation naphthyridinone aminonicotinaldehyde, Heterocyclic Compounds (More Than One Hetero Atom): Fused-Ring Systems With Two Or More Hetero Atoms, No More Than One Hetero Atom Per Ring and other aspects.Quality Control of 7-Chloro-2,3-dihydro-1,8-naphthyridin-4(1H)-one

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

On October 16, 2018, Jin, Haowen; Xu, Weiliang; Xu, Weizheng published a patent.Application of 958334-24-2 The title of the patent was Preparation method of 7-bromo-1,5-naphthyridine-3-carboxylic acid. And the patent contained the following:

The method comprises the steps of: providing 1,5-naphthyridine as a raw material, reacting to obtain 7-bromo-1,5-naphthyridin-3-carboxylate, and hydrolyzing in the presence of alkali to obtain 7-bromo-1,5-naphthyridin-3-carboxylate. The method has the advantages of simple process, low cost, accessible raw material, easy post-treatment, and high yield. The method is suitable for mass production The experimental process involved the reaction of Methyl 7-bromo-1,5-naphthyridine-3-carboxylate(cas: 958334-24-2).Application of 958334-24-2

The Article related to bromonaphthyridine carboxylic acid preparation naphthyridine bromination carbonylation, Heterocyclic Compounds (More Than One Hetero Atom): Fused-Ring Systems With Two Or More Hetero Atoms, No More Than One Hetero Atom Per Ring and other aspects.Application of 958334-24-2

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

Da Settimo, Antonio; Biagi, Giuliana; Primofiore, Giampaolo; Ferrarini, Pier Luigi; Livi, Oreste; Marini, Anna Maria published an article in 1980, the title of the article was Synthesis of some 3,7-disubstituted quino[3,2-c][1,8]naphthyridines.Application In Synthesis of 7-Chloro-2,3-dihydro-1,8-naphthyridin-4(1H)-one And the article contains the following content:

Quinonaphthyridines I (R = Me, Br, Cl, EtO, NH2; R1 = Me, Et; R2 = R3 = H) were prepared in 13-95% yields by cyclizing II with o-H2NC6H4COR1. Heating I (R2 = R3 = H) in PhNO2 gave I (R2R3 = bond). The experimental process involved the reaction of 7-Chloro-2,3-dihydro-1,8-naphthyridin-4(1H)-one(cas: 76629-10-2).Application In Synthesis of 7-Chloro-2,3-dihydro-1,8-naphthyridin-4(1H)-one

The Article related to quinonaphthyridine, naphthyridinone phenone cyclization, acetophenone naphthyridinone cyclization, benzophenone naphthyridinone cyclization, Heterocyclic Compounds (More Than One Hetero Atom): Fused-Ring Systems With Two Or More Hetero Atoms, No More Than One Hetero Atom Per Ring and other aspects.Application In Synthesis of 7-Chloro-2,3-dihydro-1,8-naphthyridin-4(1H)-one

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

On May 14, 2015, Inukai, Takayuki; Takeuchi, Jun; Yasuhiro, Tomoko; Wolf, Mark Allan; Pawal, Vijay Dattaram; Chakrabarti, Anjan; Chittimalla, Santhosh Kumar published a patent.HPLC of Formula: 869640-41-5 The title of the patent was Pyrrolopyrimidine derivative and its use for pharmaceutical composition for prevention and/or treatment of Axl-related disease. And the patent contained the following:

The compound represented by general formula I [R1 = (un)substituted C1-8 alkyl, (un)substituted C3-7 carbocycle, 4- to 7-membered heterocycle; R2 = (un)substituted C1-8 alkyl, (un)substituted C2-8 alkenyl, (un)substituted C2-8 alkynyl, OH, (un)substituted C3-7 carbocycle, (un)substituted 4- to 7-membered heterocycle, halo, etc.; R3 = C1-4 (halo)alkyl, halo, OH, C1-4 (halo)alkoxy; R4 = H, (un)substituted C1-8 alkyl, (un)substituted C3-10 carbocycle, (un)substituted 4- to 10-membered heterocycle; R5 = H, C1-4 (halo)alkyl, halo; ring1 = 5- to 7-membered cyclic group; m, n = 0-3] has strong Axl inhibition activity by means of a pyridone ring structure being introduced into a pyrrolopyrimidine skeleton, and so the result can serve as a treatment agent for Axl-related diseases, for example cancers such as acute myeloid leukemia, melanoma, breast cancer, pancreatic cancer, and glial tumors, renal disease, immune system disorders, and cardiovascular disease. Thus, N-[5-(4-amino-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-pyridinyl]-2′,5′-dioxo-1′-phenyl-2′,5′,6′,8′-tetrahydro-1’H-spiro(cyclopropane-1,7′-quinoline)-3′-carboxamide (preparation given) inhibited Axl with IC50 of 0.0097 μmol. The experimental process involved the reaction of 7-Benzyl-5,6,7,8-tetrahydro-1,7-naphthyridin-2(1H)-one(cas: 869640-41-5).HPLC of Formula: 869640-41-5

The Article related to pyrrolopyrimidine preparation pharmaceutical axl inhibitor disease therapy anticancer, immune system cardiovascular disease treatment axl inhibitor pyrrolopyrimidine preparation and other aspects.HPLC of Formula: 869640-41-5

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

On April 20, 2011, Kroth, Heiko; Froestl, Wolfgang; Pfeifer, Andrea; Muhs, Andreas published a patent.Product Details of 445490-78-8 The title of the patent was Preparation of 2,6-diaminopyridine compounds for treating diseases associated with amyloid proteins, especially ocular diseases. And the patent contained the following:

The invention is related to the preparation of diaminopyridines I [the pyridine rings A, B, and C are independently (un)substituted by ≥1 substituents selected from alkyl, NH2 and derivatives, CN, NO2, CO2H, etc.; R1, R2 = independently H, (un)substituted 5-10 membered heteroaryl, alkynyl, cycloalkyl, etc.; L1, L2 = independently NR3CR4R5(CR6R7)p, (CR8R9)qCR10R11NR12; R3, R12 = independently H, CH(:NOH) and derivatives, CONH2 and derivatives, (un)substituted 5-10 membered heterocycloalkylalkyl, etc.; R4-11 = independently SO2NH2 and derivatives, aminocarbonylalkyl, halo, OCONH2 and derivatives, etc.; p = 1-2; q = 0-2] and their pharmaceutical acceptable salts that can be employed in the treatment of a group of disorders and abnormalities associated with amyloid protein and of diseases or conditions associated with amyloid-like proteins. The invention is also related to the use of I in the treatment of ocular diseases associated with pathol. abnormalities/changes in the tissues of the visual system. Thus, II was prepared by a multi-step synthesis from 2-bromo-6-methylpyridine and inhibited the aggregation of amyloid beta 1-42 peptide in a thioflavin T spectrofluorescence assay (IC50 = 12.9 mM). 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).Product Details of 445490-78-8

The Article related to pyridinediamine preparation amyloid beta protein abnormality ocular disease, glaucoma intraocular pressure amyloidosis naphthyridinylalkyl pyridinylalkyl pyridinediamine preparation and other aspects.Product Details of 445490-78-8

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

On April 21, 2011, Kroth, Heiko; Froestl, Wolfgang; Pfeifer, Andrea; Muhs, Andreas published a patent.SDS of cas: 445490-78-8 The title of the patent was Preparation of 2,6-diaminopyridine compounds for treating diseases associated with amyloid or amyloid-like proteins, especially ocular diseases. And the patent contained the following:

The invention is related to the preparation of diaminopyridines I [the pyridine rings A, B, and C are independently (un)substituted by ≥1 substituents selected from alkyl, NH2 and derivatives, CN, NO2, CO2H, etc.; R1, R2 = independently H, (un)substituted 5-10 membered heteroaryl, alkynyl, cycloalkyl, etc.; L1, L2 = independently NR3CR4R5(CR6R7)p, (CR8R9)qCR10R11NR12; R3, R12 = independently H, CH(:NOH) and derivatives, CONH2 and derivatives, (un)substituted 5-10 membered heterocycloalkylalkyl, etc.; R4-11 = independently SO2NH2 and derivatives, aminocarbonylalkyl, halo, OCONH2 and derivatives, etc.; p = 1-2; q = 0-2] and their pharmaceutical acceptable salts that can be employed in the treatment of a group of disorders and abnormalities associated with amyloid protein and of diseases or conditions associated with amyloid-like proteins. The invention is also related to the use of I in the treatment of ocular diseases associated with pathol. abnormalities/changes in the tissues of the visual system. Thus, II was prepared by a multi-step synthesis from 2-bromo-6-methylpyridine and inhibited the aggregation of amyloid beta 1-42 peptide in a thioflavin T spectrofluorescence assay (IC50 = 12.9 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).SDS of cas: 445490-78-8

The Article related to pyridinediamine preparation amyloid beta protein abnormality ocular disease, glaucoma intraocular pressure amyloidosis naphthyridinylalkyl pyridinylalkyl pyridinediamine preparation and other aspects.SDS of cas: 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

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 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