Pyridine-derivatives

Breant, P.; Marsais, F.; Queguiner, G. published an article in 1983, the title of the article was Regioselective lithiation of 3-pyridylsulfonic acid derivatives: a convenient route to various new 4-substituted 3-pyridylsulfonamides.Computed Properties of 636-73-7 And the article contains the following content:

Pyridinesulfonamides I [NR2 = piperidino, morpholino, pyrrolidino; R1 = C(OH)Ph2, (un)substituted α-hydroxybenzyl] were prepared from lithiopyridines II and the resp. carbonyl compounds Amide III was treated at -60° with (Me2CH)2NH and BuLi in Et2O, PhCHO in Et2O was added at -70°, and the mixture was stirred 2 h at -70° to give I [NR2 = piperidino, R1 = PhCH(OH)]. The experimental process involved the reaction of Pyridine-3-sulfonic acid(cas: 636-73-7).Computed Properties of 636-73-7

The Article related to addition lithiopyridinesulfonamide benzaldehyde, pyridinesulfonamide hydroxybenzyl, hydroxybenzylpyridinesulfonamide, Heterocyclic Compounds (One Hetero Atom): Pyridines and other aspects.Computed Properties of 636-73-7

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

On March 24, 2009, Yuan, Chester Chenguang published a patent.Name: 6-(tert-Butyl)pyridin-3-amine The title of the patent was Preparation of substituted arylamine derivatives, particularly 2-aminonicotinamides, as antitumor agents. And the patent contained the following:

The invention is related to the preparation of a compound or a pharmaceutically acceptable derivative thereof, wherein the compound is 3-[(7-isoquinolinyl)amino]-N-[3-methyl-4-(1-methylethyl)phenyl]-3-pyridinecarboxamide are prepared and to its use as an effective agent for treatment of angiogenesis and related diseases such as cancer. Thus, acylation of 7-amino-4,4-dimethyl-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-Bu ester with 2-chloropyridine-3-carbonyl chloride, followed by amination of the chloride intermediate (no data) with 7-aminoisoquinoline and deprotection gave 2-[(7-isoquinolinyl)amino]-N-(1,2,3,4-tetrahydro-4,4-dimethyl-7-isoquinolinyl)-3-piperidinecarboxamide monohydrochloride. Selected compounds of the invention inhibited VEGF-stimulated HUVEC proliferation at a level below 1 μM. In the tumor model, compounds of the invention are active at doses less than 150 mpk. The experimental process involved the reaction of 6-(tert-Butyl)pyridin-3-amine(cas: 39919-70-5).Name: 6-(tert-Butyl)pyridin-3-amine

The Article related to arylamine preparation antitumor angiogenesis inhibitor, pyridinecarboxamide amino preparation neoplasm vegf inhibitor, Heterocyclic Compounds (One Hetero Atom): Pyridines and other aspects.Name: 6-(tert-Butyl)pyridin-3-amine

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Balicki, R.; Kaczmarek, L.; Sobotka, W.; Ejmocki, Z. published an article in 1989, the title of the article was Insect chitin formation inhibitors. III. Synthesis and activity of some bis[3-(2,6-dihalobenzoyl)-1-ureido]bipyridines.COA of Formula: C10H10N4 And the article contains the following content:

Eight title compounds I (R, R1 = Cl, F) were prepared in 69-89% yields by a 4-step procedure starting from nitriles II. I have significant activity against house-flies (no data). The experimental process involved the reaction of [2,2′-Bipyridine]-3,3′-diamine(cas: 75449-26-2).COA of Formula: C10H10N4

The Article related to ureidobipyridine preparation insecticide, bipyridine ureido preparation insecticide, insect chitin formation inhibitor, Heterocyclic Compounds (One Hetero Atom): Pyridines and other aspects.COA of Formula: C10H10N4

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

On December 7, 2017, Kato, Taku; Sakamoto, Toshiaki; Niwa, Yasuki; Sawamoto, Daisuke; Otani, Naohito; Kanbe, Misaki published a patent.COA of Formula: C9H14N2 The title of the patent was Preparation of aromatic carboxylic acid amides having TRPM8 blocking effect. And the patent contained the following:

Disclosed are compounds I [ring A = benzene or thiophene; X1 = CR11 or nitrogen atom; R11 = H or (un)substituted alkyl; X2, X3 = independently CH or nitrogen atom; ring C = monocyclic ring; R1 = (un)substituted alkyl, (un)substituted alkanoyl, cyano, etc.; R1 is substituted on the adjacent position to the point of attachment to ring B; R2 = H, (un)substituted alkyl or halo; R3 = cyano, -Ra, -N(Rb)(Rc), etc.; Ra = (un)substituted alkyl, (un)substituted non-aromatic heterocycle-methyl-, (un)substituted alkenyl, etc.; Rb = (un)substituted alkyl, (un)substituted alkenyl, (un)substituted cycloalkyl, etc.; Rc = H, (un)substituted alkyl, (un)substituted alkenyl, etc.; R4 = (un)substituted alkyl, (un)substituted alkanoyl, cyano, etc.; n = 0 or 1; R5 = H, (un)substituted alkyl, hydroxy, etc.; when n is 1, R4 and R5, together with ring C, may combine to form a bicyclic ring; or pharmacol. acceptable salts thereof]. For example, compound II was prepared from 5-bromo-3-fluoropyridine-2-carboxylic acid Et ester via conversion into 3-iodo-5-[2-(trifluoromethyl)phenyl]pyridine-2-carboxylic acid followed by amidation with 5-amino-2-trifluoromethylpyridine and reaction with 5-methyl-2-pyrrolidone. In TRPM8 blocking test, 361-example of I showed IC50 values (nmol/L) ranging from 0.2 to 2760, e.g., IC50 of II was 4 nmol/L. Of note, compounds I are useful for the treatment of chronic pain. The experimental process involved the reaction of 6-(tert-Butyl)pyridin-3-amine(cas: 39919-70-5).COA of Formula: C9H14N2

The Article related to aromatic carboxylic acid amide preparation trpm8 blocker, chronic pain treatment aromatic carboxylic acid amide trpm8 blocking, Heterocyclic Compounds (One Hetero Atom): Pyridines and other aspects.COA of Formula: C9H14N2

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

On March 17, 2016, Kato, Taku; Sakamoto, Toshiaki; Niwa, Yasuki; Sawamoto, Daisuke; Ohtani, Naohito; Kanbe, Misaki published a patent.HPLC of Formula: 39919-70-5 The title of the patent was Preparation of aromatic carboxylic acid amides having TRPM8 blocking effect. And the patent contained the following:

Disclosed are compounds I [ring A = benzene or thiophene; X1 = CR11 or nitrogen atom; R11 = H or (un)substituted alkyl; X2, X3 = independently CH or nitrogen atom; ring C = monocyclic ring; R1 = (un)substituted alkyl, (un)substituted alkanoyl, cyano, etc.; R1 is substituted on the adjacent position to the point of attachment to ring B; R2 = H, (un)substituted alkyl or halo; R3 = cyano, -Ra, -N(Rb)(Rc), etc.; Ra = (un)substituted alkyl, (un)substituted non-aromatic heterocycle-methyl-, (un)substituted alkenyl, etc.; Rb = (un)substituted alkyl, (un)substituted alkenyl, (un)substituted cycloalkyl, etc.; Rc = H, (un)substituted alkyl, (un)substituted alkenyl, etc.; R4 = (un)substituted alkyl, (un)substituted alkanoyl, cyano, etc.; n = 0 or 1; R5 = H, (un)substituted alkyl, hydroxy, etc.; when n is 1, R4 and R5, together with ring C, may combine to form a bicyclic ring; or pharmacol. acceptable salts thereof]. For example, compound II was prepared from 5-bromo-3-fluoropyridine-2-carboxylic acid Et ester via conversion into 3-iodo-5-[2-(trifluoromethyl)phenyl]pyridine-2-carboxylic acid followed by amidation with 5-amino-2-trifluoromethylpyridine and reaction with 5-methyl-2-pyrrolidone. In TRPM8 blocking test, 361-example of I showed IC50 values (nmol/L) ranging from 0.2 to 2760, e.g., IC50 of II was 4 nmol/L. Of note, compounds I are useful for the treatment of chronic pain. The experimental process involved the reaction of 6-(tert-Butyl)pyridin-3-amine(cas: 39919-70-5).HPLC of Formula: 39919-70-5

The Article related to aromatic carboxylic acid amide preparation trpm8 blocker, chronic pain treatment aromatic carboxylic acid amide trpm8 blocking, Heterocyclic Compounds (One Hetero Atom): Pyridines and other aspects.HPLC of Formula: 39919-70-5

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

On March 23, 2017, Watanabe, Atsushi; Sato, Yuuki; Ogura, Keiji; Tatsumi, Yoshiyuki published a patent.Synthetic Route of 25813-24-5 The title of the patent was Preparation of biaryl derivatives as antifungal agents and medicine containing them. And the patent contained the following:

Biaryl derivatives represented by general formula I (ring A, X1, X2, X3, Y, Z, R2a, R3, and Q are defined below) or salts thereof having excellent antifungal activity against Trichophyton, which is a major causative organism of superficial mycoses. Ring A, X1, X2, X3, Y, Z, Q, and R3 are defined as [ring A = each (un)substituted Ph or 5- or 6-membered heteroaryl each optionally fused to form (un)substituted condensed ring; Q = CH2, CF2, S(O), SO2, C(O), NH, or S; X1, X2, X3 = CR1 or N; Y = CH or N; Z = CR2b or N; R1 = H, halo, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy, or C1-6 haloalkoxy; R3 = H, halo, or each (un)substituted C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy, C1-6 haloalkoxy, C3-7 cycloalkyl, C2-6 alkenyl, C2-6 alkynyl, or aralkyl]. R2a and R2b are defined as [R2a, R2b = H, halo, HO, cyano, formyl, pentafluorosulfanyl, Q1, or each (un)substituted C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy, C1-6 haloalkoxy, C1-4 alkoxy-C1-4 alkyl, C1-4 alkoxy-C1-4 haloalkyl, C1-6 alkyl carbonyl, C1-6 alkoxycarbonyl, C1-6 alkylcarbonyloxy, C3-7 cycloalkyl, heterocycloalkyl, heterocycloalkyloxy, C2-6 alkenyl, C2-6 alkenyloxy, C2-6 alkenyl-C1-6 alkyl, C2-6 alkenyl-C1-6 alkoxy, C2-6 alkenyloxy-C1-4 alkoxy, C2-6 alkenyloxy-C1-4 haloalkyl, C2-6 alkenyloxy-C1-4 haloalkoxy, C2-6 alkynyl, C2-6 alkynyloxy, C2-6 alkynyl-C1-6 alkyl, C2-6 alkynyl-C1-6 alkoxy, C2-6 alkynyloxy-C1-4 alkyl, C2-6 alkynyloxy-C1-4 alkoxy, C2-6 alkynyloxy-C1-4 haloalkyl, C2-6 alkynyloxy-C1-4 haloalkoxy, NH2, C1-6 alkylthio, C1-6 haloalkylthio; ring B = each (un)substituted carbocyclic or heterocyclic ring; L = a single bond, (CH2)p, O(CH2)p, (CH2)pO, (CH2)pO(CH2)q, NRc(CH2)p , (CH2)pNRc, or (CH2)pNRc(CH2)q; p, q = 1, 2, or 3; one or a plural number of H atoms of each (CH2)p or (CH2)q is optionally substituted with halo, C1-4 alkyl, or C3-7 cycloalkyl; Rc = H or C1-6 alkyl; when Z = CR2b, R2a and R2b together with the carbon atoms to which they are bonded form each (un)substituted carbocyclic or heterocyclic ring]. The biaryl derivatives I include arylpyridine or heterocyclylpyridine derivatives, e.g. 3-phenyl-2-[(pyridin-3-yl)oxy]pyridine, 2-[(pyridin-3-yl)oxy]-3,3′-bipyridine, 5-[2-[(pyridin-3-yl)oxy]pyridin-3-yl]isoquinoline, 8-[2-[(pyridin-3-yl)oxy]pyridin-3-yl]quinoline, 3-(2,3-dihydrobenzofuran-7-yl)-2-[(pyridin-3-yl)oxy]pyridine, 5-[2-[(pyridin-3-yl)oxy]pyridin-3-yl]quinoxaline, and 3-(chroman-8-yl)-2-[(pyridin-3-yl)oxy]pyridine derivatives Thus, etherification of 3-bromo-2-chloropyridine with 6-(trifluoromethyl)pyridin-3-ol in the presence of Cs2CO3 in DMSO with stirring at 120° for 18 h gave 76% 3-[(3-bromopyridin-2-yl)oxy]-6-(trifluoromethyl)pyridine (II). Coupling of II with 2-methoxyphenylboronic acid in the presence of bis[di-tert-butyl(4-dimethylaminophenyl)phosphine]palladium(II) and Cs2CO3 in aqueous dioxane solution with stirring at 120° for 30 min under microwave irradiation gave 76% 3-(2-methoxyphenyl)-2-[[6-(trifluoromethyl)pyridin-3-yl]oxy]pyridine (III). III showed min. inhibitory concentration of ≤0.1 μg/mL against Trichophyton mentagrophytes and T. rubrum. The experimental process involved the reaction of 3,5-Dibromo-4-methoxypyridine(cas: 25813-24-5).Synthetic Route of 25813-24-5

The Article related to bipyridine phenylpyridine pyridylquinoline pyrimidinylpyridine heterocyclylpyridine preparation antifungal, biaryl preparation antifungal agent, Heterocyclic Compounds (One Hetero Atom): Pyridines and other aspects.Synthetic Route of 25813-24-5

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

On September 20, 2018, Watanabe, Atsushi; Sato, Yuki; Ogura, Keiji; Tatsumi, Yoshiyuki published a patent.Recommanded Product: 3,5-Dibromo-4-methoxypyridine The title of the patent was Preparation of biaryl derivatives as antifungal agents and medicine containing them. And the patent contained the following:

Biaryl derivatives represented by general formula I (ring A, X1, X2, X3, Y, Z, R2a, R3, and Q are defined below) or salts thereof having excellent antifungal activity against Trichophyton which is a major causative organism of superficial mycoses are prepared Ring A, X1, X2, X3, Y, Z, Q, and R3 are defined as [ring A = each (un)substituted Ph or 5- or 6-membered heteroaryl each optionally fused to form (un)substituted condensed ring; Q = CH2, CF2, S(O), SO2, C(O), NH, or S; X1, X2, X3 = CR1 or N; Y = CH or N; Z = CR2b or N; R1 = H, halo, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy, or C1-6 haloalkoxy; R3 = H, halo, or each (un)substituted C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy, C1-6 haloalkoxy, C3-7 cycloalkyl, C2-6 alkenyl, C2-6 alkynyl, or aralkyl]. R2a and R2b are defined as [R2a, R2b = H, halo, HO, cyano, formyl, pentafluorosulfanyl, Q1, or each (un)substituted C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy, C1-6 haloalkoxy, C1-4 alkoxy-C1-4 alkyl, C1-4 alkoxy-C1-4 haloalkyl, C1-6 alkyl carbonyl, C1-6 alkoxycarbonyl, C1-6 alkylcarbonyloxy, C3-7 cycloalkyl, heterocycloalkyl, heterocycloalkyloxy, C2-6 alkenyl, C2-6 alkenyloxy, C2-6 alkenyl-C1-6 alkyl, C2-6 alkenyl-C1-6 alkoxy, C2-6 alkenyloxy-C1-4 alkoxy, C2-6 alkenyloxy-C1-4 haloalkyl, C2-6 alkenyloxy-C1-4 haloalkoxy, C2-6 alkynyl, C2-6 alkynyloxy, C2-6 alkynyl-C1-6 alkyl, C2-6 alkynyl-C1-6 alkoxy, C2-6 alkynyloxy-C1-4 alkyl, C2-6 alkynyloxy-C1-4 alkoxy, C2-6 alkynyloxy-C1-4 haloalkyl, C2-6 alkynyloxy-C1-4 haloalkoxy, NH2, C1-6 alkylthio, C1-6 haloalkylthio; ring B = each (un)substituted carbocyclic or heterocyclic ring; L = a single bond, (CH2)p, O(CH2)p, (CH2)pO, (CH2)pO(CH2)q, NRc(CH2)p , (CH2)pNRc, or (CH2)pNRc(CH2)q; p, q = 1, 2, or 3; one or a plural number of H atoms of each (CH2)p or (CH2)q is optionally substituted with halo, C1-4 alkyl, or C3-7 cycloalkyl; Rc = H or C1-6 alkyl; when Z = CR2b, R2a and R2b together with the carbon atoms to which they are bonded form each (un)substituted carbocyclic or heterocyclic ring]. The biaryl derivatives I include arylpyridine or heterocyclylpyridine derivatives, e.g. 3-phenyl-2-[(pyridin-3-yl)oxy]pyridine, 2-[(pyridin-3-yl)oxy]-3,3′-bipyridine, 5-[2-[(pyridin-3-yl)oxy]pyridin-3-yl]isoquinoline, 8-[2-[(pyridin-3-yl)oxy]pyridin-3-yl]quinoline, 3-(2,3-dihydrobenzofuran-7-yl)-2-[(pyridin-3-yl)oxy]pyridine, 5-[2-[(pyridin-3-yl)oxy]pyridin-3-yl]quinoxaline, and 3-(chroman-8-yl)-2-[(pyridin-3-yl)oxy]pyridine derivatives Thus, etherification of 3-bromo-2-chloropyridine with 6-(trifluoromethyl)pyridin-3-ol in the presence of Cs2CO3 in DMSO with stirring at 120° for 18 h gave 76% 3-[(3-bromopyridin-2-yl)oxy]-6-(trifluoromethyl)pyridine (II). Coupling of II with 2-methoxyphenylboronic acid in the presence of bis[di-tert-butyl(4-dimethylaminophenyl)phosphine]palladium(II) and Cs2CO3 in aqueous dioxane solution with stirring at 120° for 30 min under microwave irradiation gave 76% 3-(2-methoxyphenyl)-2-[[6-(trifluoromethyl)pyridin-3-yl]oxy]pyridine (III). III showed min. inhibitory concentration of ≤0.1 μg/mL against Trichophyton mentagrophytes and T. rubrum. The experimental process involved the reaction of 3,5-Dibromo-4-methoxypyridine(cas: 25813-24-5).Recommanded Product: 3,5-Dibromo-4-methoxypyridine

The Article related to bipyridine phenylpyridine pyridylquinoline pyrimidinylpyridine heterocyclylpyridine preparation antifungal, biaryl preparation antifungal agent, Heterocyclic Compounds (One Hetero Atom): Pyridines and other aspects.Recommanded Product: 3,5-Dibromo-4-methoxypyridine

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

On September 20, 2019, Yu, Miao; Strotman, Neil A.; Savage, Scott A.; Leung, Simon; Ramirez, Antonio published an article.Reference of Pyridine-3-sulfonic acid The title of the article was A Practical and Robust Multistep Continuous Process for Manufacturing 5-Bromo-N-(tert-butyl)pyridine-3-sulfonamide. And the article contained the following:

A multistep continuous flow process involving (1) magnesium-halogen exchange, (2) sulfonylation with sulfuryl chloride, and (3) reaction with tert-butylamine was developed for the synthesis of an arylsulfonamide pharmaceutical intermediate in the synthesis of BMS-919373. The process was successfully implemented, including a robust control strategy to manage the levels of several process impurities, to produce 76 kg of 5-bromo-N-(tert-butyl)pyridine-3-sulfonamide (I). As the instability of the reactive intermediates and existence of strong exotherms made a batch process unsuitable for production beyond a 1 kg scale, the alternative continuous process led to a practical and robust manufacturing route to the active pharmaceutical ingredient. The experimental process involved the reaction of Pyridine-3-sulfonic acid(cas: 636-73-7).Reference of Pyridine-3-sulfonic acid

The Article related to bromo tertbutyl pyridine sulfonamide preparation multistep continuous process, magnesium halogen exchange sulfonylation amination continuous flow, Heterocyclic Compounds (One Hetero Atom): Pyridines and other aspects.Reference of Pyridine-3-sulfonic acid

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

On June 28, 2007, Glatthar, Ralf; Orain, David; Spanka, Carsten published a patent.SDS of cas: 85614-89-7 The title of the patent was Preparation of nicotinic acid derivatives as modulators of mGluR5 metabotropic glutamate receptors. And the patent contained the following:

Title compounds [I; R1 = (substituted) alkyl, PhCH2; R2 = H, (substituted) alkyl, PhCH2; R1R2N = (substituted) heterocyclyl; R3, R4 = halo, OH, alkyl, alkoxy, amino, alkylamino, dialkylamino; Q, V, W = CH, CR4, N; X = CH, N; Y = CH, CR3, N; Z = CR6aR6b, NR5, O; R5 = H, OH; R6a, R6b = H, halo, OH, amino, alkyl, alkoxy, haloalkyl; provided that Q, V, W are not all N], were prepared Thus, 6-chloro-N,N-diethylnicotinamide (preparation given) and 4-chloroaniline were heated in aqueous HOAc in a sealed vial at 100° overnight to give after chromatog. 6-(4-chlorophenylamino)-N,N-diethylnicotinamide hydrochloride. The latter at 10 μM gave 95% inhibition of mGluR5 activity. The experimental process involved the reaction of Ethyl 5-methyl-6-oxo-1,6-dihydropyridine-3-carboxylate(cas: 85614-89-7).SDS of cas: 85614-89-7

The Article related to nicotinic acid derivative preparation mglur5 metabotropic glutamate receptor modulator, gastrointestinal nervous system urinary tract disorder treatment, Heterocyclic Compounds (One Hetero Atom): Pyridines and other aspects.SDS of cas: 85614-89-7

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Tanaka, Katsumasa; Hattori, Hiroshi; Yabe, Ryota; Nishimura, Takahiro published an article in 2022, the title of the article was Ir-Catalyzed cyclization of α,ω-dienes with an N-methyl group via two C-H activation steps.Related Products of 156267-13-9 And the article contains the following content:

Iridium-catalyzed sp3 C-H alkylation of an N-Me group with 1,5- and 1,6-dienes proceeded to give five- and six-membered carbocyclic compounds, resp., in high yields. The reaction involved intermol. alkylation of the N-Me group with a vinyl moiety and subsequent intramol. cyclization at the β-position of the initially formed alkylated intermediate. The reaction using a chiral bidentate phosphine ligand enabled the asym. synthesis of the cyclic compounds The experimental process involved the reaction of N,3-Dimethylpyridin-2-amine(cas: 156267-13-9).Related Products of 156267-13-9

The Article related to methylpyridinamine diene iridium catalyst regioselective bond activation alkylation cyclization, cycloalkylmethylpyridinamine enantioselective preparation, Heterocyclic Compounds (One Hetero Atom): Pyridines and other aspects.Related Products of 156267-13-9

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem