cas 55676-21-6, 3-ACETYL-2-CHLOROPYRIDINE | Articles data

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Difluorocarbene-triggered cyclization: Synthesis of (hetero)arene-fused 2,2-difluoro-2,3-dihydrothiophenes
An efficient method for the synthesis of (hetero)arene-fused 2,2-difluoro-2,3-dihydrothiophene derivatives using readily available sodium chlorodifluoroacetate (ClCF2CO2Na) has been developed. This transformation is achieved through a combination of a thi
Liang, Huamin,Liu, Ran,Zhou, Min,Fu, Yue,Ni, Chuanfa,Hu, Jinbo
supporting information
p. 7047 - 7051
(2020/09/15)

INDAZOLE CONTAINING MACROCYCLES AND THERAPEUTIC USES THEREOF
Indazole macrocycle compounds of formula (I) for treating various diseases and pathologies are disclosed. More particularly, the present invention concerns the use of an indazole macrocycle compound or analogs thereof, in the treatment of disorders characterized by the activation of Wnt pathway signaling (e.g., cancer, abnormal cellular proliferation, angiogenesis, fibrotic disorders, bone or cartilage diseases, and osteoarthritis), the modulation of cellular events mediated by Wnt pathway signaling, as well as genetic diseases and neurological conditions/disorders/diseases due to mutations or dysregulation of the Wnt pathway and/or of one or more of Wnt signaling components. Also provided are methods for treating Wnt-related disease states. Formula (I)
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Paragraph 0341-0342

(2020/01/08)

Strategies to develop selective CB2 receptor agonists from indole carboxamide synthetic cannabinoids
Activation of the CB2 receptor is an attractive therapeutic strategy for the treatment of a wide range of inflammatory diseases. However, receptor subtype selectivity is necessary in order to circumvent the psychoactive effects associated with activation of the CB1 receptor. We aimed to use potent, non-selective synthetic cannabinoids designer drugs to develop selective CB2 receptor agonists. Simple structural modifications such as moving the amide substituent of 3-amidoalkylindole synthetic cannabinoids to the 2-position and bioisosteric replacement of the indole core to the 7-azaindole scaffold are shown to be effective and general strategies to impart receptor subtype selectivity. 2-Amidoalkylindole 16 (EC50 CB1 > 10 μM, EC50 CB2 = 189 nM) and 3-amidoalkyl-7-azaindole 21 (EC50 CB1 > 10 μM, EC50 = 49 nM) were found to be potent and selective agonists with favourable physicochemical properties. Docking studies were used to elucidate the molecular basis for the observed receptor subtype selectivity for these compounds.
Moir, Michael,Lane, Samuel,Lai, Felcia,Connor, Mark,Hibbs, David E.,Kassiou, Michael
p. 291 - 309
(2019/07/17)

A Novel Synthesis of 1-Alkyl-2-phenyl-1,8-naphthyridin-4-one
Provided is a novel method for manufacturing 1-alkyl-2-phenyl-1,8-naphthyridin-4-one from 2-chloronicotinic acid. According to the present invention, 1-alkyl-2-phenyl-1,8-naphthyridin-4-one can be synthesized through simple reaction conditions and simple
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(2017/09/30)

High-activity iminophenylacetate compound, preparation method and applications thereof
The present invention belongs to the field of pesticides, and particularly relates to a high-activity iminophenylacetate compound, a preparation method and applications thereof. According to the present invention, the research of novel methoxy acrylate compounds is performed, a pyridine aryl ether structure is introduced into the structure of the novel methoxy acrylate compound, the research of the new compound structures is expanded, and the high-activity iminophenylacetate compound is found; and the compound has the bioactivity equal to azoxystrobin and trifloxystrobin, provides good effects on most pathogenic bacteria, especially provides significant prevention and treatment effects on Sclerotinia sclerotiorum bacterial, and is effective at a low doses.
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Paragraph 0070

(2017/08/30)

THIAZOLE DERIVATIVES FOR THE TREATMENT OF ANIMAL TRYPANOSOMIASIS
The present invention relates to a novel class of compounds of general formula (I) wherein R1, R2, R3, R4, R5, R6, R7, X and Y are as defined herein, to their use in human and veterinary medicine, and in the treatment of animal trypanosomiasis in particular, to compositions containing them, to processes for their preparation and to intermediates used in such processes.
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Page/Page column 74

(2016/10/04)

3-(3H-IMIDAZO[4,5-B]PYRIDIN-2-YL)-1H-PYRAZOLO[3,4-B]PYRIDINE AND THERAPEUTIC USES THEREOF
Azaindazole compounds for treating various diseases and pathologies are disclosed. More particularly, the present invention concerns the use of an azaindazole compound or analogs thereof, in the treatment of disorders characterized by the activation of Wnt pathway signaling (e.g., cancer, abnormal cellular proliferation, angiogenesis, fibrotic disorders, bone or cartilage diseases, and osteoarthritis), the modulation of cellular events mediated by Wnt pathway signaling, as well as genetic diseases and neurological conditions/disorders/diseases due to mutations or dysregulation of the Wnt pathway and/or of one or more of Wnt signaling components. Also provided are methods for treating Wnt-related disease states.
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Paragraph 1056

(2016/04/20)

3-(1H-IMIDAZO[4,5-C]PYRIDIN-2-YL)-1H-PYRAZOLO[3,4-B]PYRIDINE AND THERAPEUTIC USES THEREOF
Azaindazole compounds for treating various diseases and pathologies are disclosed. More particularly, the present invention concerns the use of an azaindazole compound or analogs thereof, in the treatment of disorders characterized by the activation of Wnt pathway signaling (e.g., cancer, abnormal cellular proliferation, angiogenesis, fibrotic disorders, bone or cartilage diseases, and osteoarthritis), the modulation of cellular events mediated by Wnt pathway signaling, as well as genetic diseases and neurological conditions/disorders/diseases due to mutations or dysregulation of the Wnt pathway and/or of one or more of Wnt signaling components. Also provided are methods for treating Wnt-related disease states.
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Paragraph 0703

(2016/06/01)

A novel synthesis of 1-alkyl-2-phenyl-(2,3-dihydro-) 1,8-naphthyridin-4-ones from 2-chloronicotinic acid
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Lee, Jae In
p. 1908 - 1911
(2015/07/15)

Discovery of (S)-1-(1-(Imidazo[1,2- a ]pyridin-6-yl)ethyl)-6-(1-methyl-1 H -pyrazol-4-yl)-1 H -[1,2,3]triazolo[4,5- b ]pyrazine (Volitinib) as a Highly Potent and Selective Mesenchymal-Epithelial Transition Factor (c-Met) Inhibitor in Clinical Development for Treatment of Cancer
HGF/c-Met signaling has been implicated in human cancers. Herein we describe the invention of a series of novel triazolopyrazine c-Met inhibitors. The structure-activity relationship of these compounds was investigated, leading to the identification of compound 28, which demonstrated favorable pharmacokinetic properties in mice and good antitumor activities in the human glioma xenograft model in athymic nude mice.
Jia, Hong,Dai, Guangxiu,Weng, Jianyang,Zhang, Zhulin,Wang, Qing,Zhou, Feng,Jiao, Longxian,Cui, Yumin,Ren, Yongxin,Fan, Shiming,Zhou, Jinghong,Qing, Weiguo,Gu, Yi,Wang, Jian,Sai, Yang,Su, Weiguo
supporting information
p. 7577 - 7589
(2014/12/11)

A novel synthesis of heterocyclic analogues of thioflavanones from haloheteroaromatic carboxylic acids
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Lee, Jae In
p. 1253 - 1256
(2013/07/28)

1H-PYRAZOLO[3,4-B]PYRIDINES AND THERAPEUTIC USES THEREOF
Provided herein are compounds according to Formulas (I) or (II) and pharmaceutically acceptable salts thereof, and compositions comprising the same, for use in various methods, including treating cancer, abnormal cellular proliferation, angiogenesis, Alzheimer's disease, lung disease, osteoarthritis, idiopathic pulmonary fibrosis and neurological conditions/disorders/diseases.
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Paragraph 0494

(2013/11/19)

Synthesis and biological evaluation of imidazo[4,5-b]pyridine and 4-heteroaryl-pyrimidine derivatives as anti-cancer agents
A series of N-phenyl-imidazo[4,5-b]pyridin-2-amines, 4-indazolyl-N- phenylpyrimidin-2-amines and N-phenyl-4-pyrazolo[3,4-b]pyridin-pyrimidin-2- amines have been synthesized. Their anti-proliferative activities were tested in HCT-116 human colon carcinoma and MCF-7 breast carcinoma cell lines. Many exhibited potent anti-proliferative and CDK9 inhibitory activities. A lead compound 18b demonstrated the ability to reduce the level of Mcl-1 anti-apoptotic protein, to activate caspase 3/7 and induce cancer cell apoptosis.
Lukasik, Pawel M.,Elabar, Sherifa,Lam, Frankie,Shao, Hao,Liu, Xiangrui,Abbas, Abdullah Y.,Wang, Shudong
p. 311 - 322
(2013/01/15)

Identification of an adamantyl azaquinolone JNK selective inhibitor
3-[4-((1S,2S,3R,5S,7S)-5-Hydroxyadamantan-2-ylcarbamoyl)benzyl] -4-oxo-1-phenyl-1,4-dihydro-[1,8]naphthyridine-2-carboxylic acid methyl ester (4) was identified as a novel, druglike and selective quinolone pan JNK inhibitor. In this communication, some of the structure-activity relationship of the azaquinolone analogues leading to 4 is discussed. The focus is on how changes at the amide functionality affected the biochemical potency, cellular potency, metabolic properties, and solubility of this class of JNK inhibitors. Optimization of these properties led to the identification of the adamantyl analogue, 4. 4 achieved proof of mechanism in both rat and mouse TNF-α challenge models.
Haynes, Nancy-Ellen,Scott, Nathan R.,Chen, Li C.,Janson, Cheryl A.,Li, Jia Kui,Lukacs, Christine M.,Railkar, Aruna,Tozzo, Effie,Whittard, Toni,Brown, Nicholas F.,Cheung, Adrian Wai-Hing
supporting information
p. 764 - 768
(2012/11/14)

ADAMANTYL COMPOUNDS
The invention relates to JNK inhibitors and corresponding methods, formulations, and compositions for inhibiting JNK and treating JNK-mediated disorders. The application discloses JNK inhibitors, as described below in Formula I: wherein the variables are
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Page/Page column 41

(2012/10/18)

CERTAIN TRIAZOLOPYRIDINES AND TRIAZOLOPYRAZINES, COMPOSITIONS THEREOF AND METHODS OF USE THEREFOR
Provided are certain triazolopyridines and triazolopyrazines, compositions thereof and methods of use therefor.
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Page/Page column 13

(2012/10/08)

LONIDAMINE ANALOGUES FOR FERTILITY MANAGEMENT
Fertility management can include: administering to the subject one or more doses of a compound according to Formula I so as to reduce fertility in the subject. Fertility management can also include administering an effective amount of the compound to: impair Sertoli cell function in a male subject; inhibit spermatogenesis in the subject; reduce testis weight in the subject; reduce ovary weight in a female subject; reduce serum progesterone in the female subject; impair ovarian follicle function in the female subject; causing reversible fertility in the subject. In order to return fertility, the method can include ceasing administration of the compound to the subject so as to return fertility in the subject. The compound can be administered for irreversibly sterilizing the subject.
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Page/Page column 77

(2011/02/24)

1H-PYRAZOLO[3,4-B]PYRIDINES AND THERAPEUTIC USES THEREOF
Provided herein are compounds according to Formula (I) and pharmaceutically acceptable salts thereof, and compositions comprising the same, for use in various methods, including treating cancers such as colon, ovarian, pancreatic, breast, liver, prostate and hematologic cancers.
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Page/Page column 106; 110-111

(2011/08/03)

CERTAIN TRIAZOLOPYRIDINES AND TRIAZOLOPYRAZINES, COMPOSITIONS THEREOF AND METHODS OF USE THEREFOR
Provided are certain triazolopyridines and triazolopyrazines, compositions thereof and methods of use therefor.
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Page/Page column 24

(2011/07/30)

3-Hydroxypyrrolo[2,3-b]pyridine and related compounds - Indoxyl analogues with fused electron deficient rings
Flash vacuum pyrolysis (FVP) of 4-acetyltetrazolo[1,5-a]pyridine 5 at 400 °C provides 3-methyl isoxazolo[3,4-b]pyridine 6 whose structure was confirmed by X-ray crystallography. At higher pyrolysis temperatures, the unstable heteroindoxyl 8 was obtained, which exists as the keto form (1,2-dihydropyrrolo[2,3-b]pyridin-3-one) 8K in CDCl3 solution and the enol tautomer (3-hydroxypyrrolo[2,3-b]pyridine) 8E in DMSO. The heteroindoxyl 8 oxidatively dimerises to the heteroindigotin 9, undergoes condensation reactions at the 2-position and reacts with methoxymethylene Meldrum's acid at the 1-position. FVP of the corresponding acetyltetrazolo[1,5-a]quinoline 19 was much more complex, with 2-(cyanophenyl)acetonitrile 30 (rather than a heteroindoxyl) the major product at 750 °C. FVP of 3-acetyl-4-azidoquinoline 24 at 400 °C gave 3-methylisoxazolo[4,3-c]quinoline 33, but rearrangement to the heteroindoxyl was not observed at higher temperatures.
Gaywood, Alexander P.,McNab, Hamish
supporting information; experimental part
p. 5166 - 5173
(2010/12/25)

Indazoles, benzothiazoles, benzoisothiazoles, benzisoxazoles, pyrazolopyridines, isothiazolopyridines, and preparation and uses thereof
The present invention relates generally to the field of ligands for nicotinic acetylcholine receptors (nACh receptors), activation of nACh receptors, and the treatment of disease conditions associated with defective or malfunctioning nicotinic acetylcholine receptors, especially of the brain. Further, this invention relates to novel compounds (e.g., indazoles and benzothiazoles), which act as ligands for the α7 nACh receptor subtype, methods of preparing such compounds, compositions containing such compounds, and methods of use thereof.
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Page/Page column 75

(2010/11/26)

ANTIFUNGAL AGENTS
Compounds of formula (I), and pharmaceutically acceptable salts thereof, may be used in therapy, for example as antifungal agents: (I) wherein: Rl, R2, R3, R4, R5, R6, R7, X and X1 are as defined herein. Certain compounds of formula (I) are also provided. Compounds of formula (T), and agriculturally acceptable salts thereof, may also be used as agricultural fungicides.
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(2008/06/13)

Lonidamine analogues and their use in male contraception and cancer treatment
Novel compounds useful for inhibiting spermatogenesis and cancer treatment, and in particular as inhibitors of heat shock proteins and/or elongation factor 1 alpha.
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Page/Page column 30

(2008/06/13)

AROYLFURANES AND AROYLTHIOPHENES
The invention relates to compounds of formula (I) and of formula (II) wherein ring A is a phenyl, pyridine, pyrimidine or pyrazine ring, W and X are carbon or nitrogen, Y is oxygen or sulfur, R0 is different from hydrogen, Rx is -(C=O)R1 or cyano; R1 is hydrogen, optionally substituted hydroxy or optionally substituted amino, and the other substituents are as described in the specification. The invention further relates to methods of synthesis of such compounds, to pharmaceutical compositions containing compounds of formula (I) and of formula (II), to the use of compounds of formula (I) and of formula (II) for the preparation of a pharmaceutical composition for the treatment of neoplastic and autoimmune diseases, and to methods of treatment of neoplastic and autoimmune diseases using compounds of formula (I), of formula (II) or of pharmaceutical compositions containing same.
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Page/Page column 89

(2010/02/12)

General preparative route to benzo[g]quinolines (1-azaanthracenes)
A convenient synthetic pathway to benzo[g]quinolines (1-azaanthracenes) has been developed. The nickel catalyzed coupling of methyl 2- chloronicotinate (3a) with benzylic organo zinc reagents 2a-e led to the methyl 2-benzylic substituted nicotinates 4a-e. Treatment of methyl 2- chloro-6-methylnicotinate (3b)with 2a in a similar manner led to methyl 2- benzyl-6-methylnicotinate (4f). The coupling of 2-chloro-3-acetylpyridine (5) with benzyl zinc bromide (2a) led to 2-benzyl-3-acetylpyridine (4g). The coupling of the 2,5-dichlorobenzylic organic zinc reagent (2f) with methyl 2- choronicotinate (3a) was unselective but readily coupled with methyl 2- bromonicotinate (6) to yield methyl 2-(2,5-dichlorobenzyl)nicotinate (4h). The esters 4a-f,h on reduction with lithium aluminum hydride led to the corresponding alcohols 7a-f,h which were subsequently oxidized with manganese dioxide to the respective 2-benzylic substituted pyridine-3-carboxaldehydes 8a-f,h. In one case the coupling of benzy] zinc bromide (2a) with 2- chloropyridine-3-carboxaldehyde (9) led directly to 2-benzylpyridine-3- carboxaldehyde (8a), but in poor yield. Cyclizations of the aldehydes 8a- d,f,h or the ketone 4g with polyphosphoric acid afforded the benzo[g]quinolines 10a-d,f-h in high yields. Aldehyde 8e was cyclized to 10e using a solution of sulfuric acid in methanol. Several of the benzo[g]quinolines 10c,d could be readly converted into the benzo[q]quinoline-5,10-diones 11c,d on treatment with ammonium ceric nitrate.
Krapcho, A. Paul,Gilmor, Timothy P.
p. 445 - 452
(2007/10/03)

[3-(4-phenylpiperazin-1-yl)propyl-amino, thio and oxy]-pyridine, pyrimidine and benzene derivatives as α1 -adrenoceptor antagonists
The present invention relates to novel α 1 -adrenoceptor antagonists of Formula I: STR1 in which: p is 0 or 1;t is 0, 1 or 2;X is O, S or NR 6 (in which R 6 is hydro or (C 1-6)alkyl);Y and Z are independently CH or N;R 1 is hydro, hydroxy, halo, nitro, amino, cyano, (C 1-4)alkylthio, acetylamino, trifluoroacetylamino, methylsulfonylamino, (C 1-6)alkyl, (C 3-6)cycloalkyl, (C 3-6)cycloalkyl (C 1-4)alkyl, oxazol-2-yl, aryl, heteroaryl, aryl (C 1-4)alkyl, heteroaryl (C 1-4)alkyl, (C 1-6)alkyloxy, (C 3-6)cycloalkyloxy, (C 3-6)cycloalkyl (C 1-4)alkyloxy, 2-propynyloxy, aryloxy, heteroaryloxy, aryl (C 1-4)alkyloxy or heteroaryl (C 1-4)alkyloxy (wherein alkyl is optionally substituted with one to three halo atoms and aryl or heteroaryl is optionally substituted with one to two substituents independently selected from halo and cyano);R 2 is hydro, hydroxy, halo, cyano, (C 1-6)alkyl or (C 1-6)alkyloxy (wherein alkyl is optionally substituted with one to three halo atoms);R 3 is -C (O)R 7 (wherein R 7 is (C 1-6)alkyl, (C 3-6)cycloalkyl, di(C 1-4)alkylamino, N-(C 1-4)alkyl-N-(C 1-4)alkyloxyamino, (C 1-4)alkyl((C 1-4)alkyloxy)amino, pyrrolidin-1-yl, piperidin-1-yl, morpholin-4-yl or piperazin-1-yl);R 4 is halo, hydroxy, cyano, (C 1-6)alkyl or (C 1-6)alkyloxy; andR 5 is (C 1-6)alkyl; and the pharmaceutically acceptable salts and N-oxides thereof.
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(2008/06/13)

Magnesium chloride catalysed acylation reaction
An efficient and practical preparation of methyl ketones, via a magnesium chloride catalysed acylation reaction of dimethyl malonate with acid chlorides in the presence of tertiary base and followed by a decarbmethoxylation reaction, is described.
Kuo
p. 9233 - 9236
(2007/10/02)

Improved Synthesis of 2,3-Disubstituted Pyridines by Metallation of 2-Chloropyridine: a Convenient Route to Fused Polyheterocycles
Chemoselective directed metallation of 2-chloropyridine allows the synthesis of 2-substituted 3-carbonylated pyridines, advantage being taken of the metallation ortho-directing effect of the halogen, as well as its reactivity towards nucleophiles.Thus (2-chloro-, 2-methoxy-, and 2-amino-3-pyridyl)-ethanones and -arylmethanones as well as carbaldehydes have been prepared.Some of these ortho-disubstituted intermediates have been readily cyclized to fused polyheterocycles such as naphthiridines and aza-analoges of coumarins, xanthones, and acridones.
Trecourt, Francois,Marsais, Francis,Guengoer, Timur,Queguiner, Guy
p. 2409 - 2415
(2007/10/02)