Tag: 200-300

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 June 30, 2016, Inukai, Takayuki; Takeuchi, Jun; Yasuhiro, Tomoko published a patent.Electric Literature of 869640-41-5 The title of the patent was Preparation of quinoline derivatives for the treatment of Axl-related diseases. And the patent contained the following:

The present invention provides quinoline derivatives I [R1 = (un)substituted alkyl, carbocycle or heterocycle; R2 = (un)substituted alkyl, alkenyl, alkynyl, carbocycle, etc.; R3 = alkyl, halogen, haloalkyl or OR31; R4 = alkoxy, haloalkyl, alkyl, alkenyloxy, etc.; R31 = H, alkyl or haloalkyl; A = CH or N; L = O, NH, C(O), S, etc.; ring 1 = 5- to 7-membered cyclic group; m = 0-3; n = 0-3; q = 0-4] or their salts. For example, 2,5-dioxo-1-phenyl-1,2,5,6,7,8-hexahydro-3-quinolinecarboxylic acid was subjected to reaction with hydroxylamine hydrochloride followed by coupling with 5-[(6,7-dimethoxy-4-quinolinyl)oxy]-2-pyridinamine to provide N-[(5E)-5-[(6,7-dimethoxy-4-quinolinyl)oxy]-2-pyridinyl]-5-(hydroxyimino)-2-oxo-1-phenyl-1,2,5,6,7,8-hexahydro-3-quinolinecarboxamide, which underwent Beckmann rearrangement to provide compound II. Compound II exhibited inhibitory activity against Axl with an IC50 value of 0.0015 μM. The invention compounds have strong Axl inhibitory activities and can be useful as therapeutic agents for Axl-related diseases, for example, cancers such as acute myeloid leukemia, chronic myeloid leukemia, melanoma, breast cancer, pancreatic cancer and glioma, kidney diseases, immune system diseases and cardiovascular diseases. The experimental process involved the reaction of 7-Benzyl-5,6,7,8-tetrahydro-1,7-naphthyridin-2(1H)-one(cas: 869640-41-5).Electric Literature of 869640-41-5

The Article related to quinoline derivative preparation axl inhibitor cancer treatment, kidney disease immune system disease cardiovascular disease treatment, Heterocyclic Compounds (One Hetero Atom): Quinolines and Isoquinolines and other aspects.Electric Literature of 869640-41-5

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

On March 7, 2002, Ish, Kumar Khanna; Yi, Yu; Balekudru, Devadas; Hwang-Fun, Lu; Nizal, S. Chandrakumar published a patent.Product Details of 445490-78-8 The title of the patent was Compounds containing a pyridinylaminopropoxybicyclic ring system useful as αvβ3 antagonists. And the patent contained the following:

Title compounds were prepared for use as selective inhibitors or antagonists of the αvβ3 and/or αvβ5 integrin. Thus, the benzoxazepine I was prepared by treating 4-benzyloxysalicylaldehyde with BrCMe2CO2CH2Ph and H2NCH2CO2CMe3, debenzylating, cyclizing, reaction with 2-(3-hydroxypropylamino)pyridine 1-oxide, reduction of the N-oxide, and ester hydrolysis. The compounds showed activity in several vitronectin receptor assays. 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 pyridinylaminopropoxy bicyclic compound preparation vitronectin receptor antagonist, Heterocyclic Compounds (More Than One Hetero Atom): Other 7-Membered Rings and other aspects.Product Details of 445490-78-8

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 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 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 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 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