7579-20-6Relevant academic research and scientific papers
Selenium-catalyzed intramolecular atom- And redox-economical transformation ofo-nitrotoluenes into anthranilic acids
Jiang, Xuefeng,Li, Yiming,Lin, Zhenyang,Wang, Yuhong,Yang, Tilong
supporting information, p. 2986 - 2991 (2021/05/05)
Anthranilic acids (AAs) are significant basic chemicals used in pharmaceuticals, agrochemicals, dyes, fragrances,etc. Superfluous steps are always involved in obtaining AAs. Herein, we demonstrate a straightforward strategy to transform abundanto-nitrotoluenes into biologically and pharmaceutically significant AAs without any extra reductants, oxidants and protecting groups. Various sensitive groups, such as halogens, sulfide, aldehyde, pyridines, quinolines,etc., can be tolerated in this transformation. A hundred-gram-scale operation is realized efficiently with almost quantitative selenium recycling. Further mechanistic studies and DFT calculations disclosed the proposed atom-exchange processes and the key roles of the selenium species.
Anthranilic acid and derivatives thereof as well as synthesis method and application thereof
-
Paragraph 0113-0115, (2021/09/15)
In the reaction solvent, o-methyl (hetero) aryl nitro compound is taken as a reaction raw material and is used for water. The anthranilic acid and its derivatives are synthesized by the action of a catalyst, a base and an additive. The synthetic method has the advantages of cheap and easily available raw materials, simple reaction operation, high yield and excellent functional group tolerance, and provides a simple and efficient method for synthesizing o-aminobenzoic acid which is widely used in the aspects of dyes, medicines, pesticides, spices and the like. The invention further discloses the anthranilic acid and derivatives and application thereof, and has a wide application prospect.
TRICYCLIC HETEROARYL COMPOUNDS USEFUL AS IRAK4 INHIBITORS
-
Page/Page column 51-52, (2021/02/12)
Disclosed are compounds of Formula (I) or a salt or prodrug thereof, wherein: X11 and X22 are independently C or N, provided that zero or one of X11 and X22 is N; Ring A represented by the structure is: or; and Q, R11, R22, R33, R44, R66, and p are define herein. Also disclosed are methods of using such compounds as modulators of IRAK4, and pharmaceutical compositions comprising such compounds. These compounds are useful in treating, preventing, or slowing inflammatory and autoimmune diseases, or in the treatment of cancer.
Synthesis method of 3-amino methyl isonicotinate
-
Paragraph 0033-0035; 0048-0050; 0063-0065, (2021/09/15)
The invention discloses a synthesis method of 3-amino methyl isonicotinate, wherein the synthesis method comprises the steps: by taking 4-trifluoromethyl nicotinic acid as an initial raw material, sequentially carrying out acylation condensation series connection, Hofmann degradation, hydrolysis and esterification reaction to obtain the 3-amino methyl isonicotinate. The synthesis method has the advantages of mild reaction conditions, high yield, low cost, easily available raw materials, and realization of industrial production, the thionyl chloride reaction liquid can be repeatedly used, the utilization rate of the raw materials is improved, the resource waste is reduced, the pollution is reduced, the production cost of the whole process is furthest reduced, and the application value is extremely high.
Method for rapidly and efficiently synthesizing 3-aminoisonicotinic acid methyl ester (by machine translation)
-
Paragraph 0016; 0018; 0019; 0021; 0022; 0024; 0025, (2020/05/14)
Of the method for rapidly and efficiently synthesizing 3 - aminoisonicotinic acid methyl ester, through nitration, reduction, to obtain the 3 -aminoisonicotinic acid methyl ester, disclosed by the invention can be repeatedly utilized 3 - to improve the utilization rate, of the raw material and reduce the resource waste, to the maximum reduction . of the whole process . The method comprises the following steps: synthesizing,aminoisonicotinic acid methyl ester in a high, total yield; and reducing resource waste. (by machine translation)
High-yield synthesis method of methyl 3-aminoisonicotinate
-
Sheet 0013; 0015; 0016; 0019;0020; 0023; 0024, (2020/05/01)
The invention belongs to the field of chemical pharmacy, and particularly discloses a high-yield synthesis method of methyl 3-aminoisonicotinate. According to the high-yield synthesis method, 4-picolinic acid is used as a raw material and subjected to brominating, ammonifying and esterifying to obtain methyl 3-aminoisonicotinate. The high-yield synthesis method of methyl 3-aminoisonicotinate has the advantages of mild reaction conditions, high total yield, realization of repeated use of a 3-bromo-4-picolinic acid reaction waste filtrate, improvement of the utilization rate of the raw material,reduction of resource waste, maximum reduction of the production cost of the whole process, and extremely high application value.
Design, Synthesis, and Evaluation of the Highly Selective and Potent G-Protein-Coupled Receptor Kinase 2 (GRK2) Inhibitor for the Potential Treatment of Heart Failure
Okawa, Tomohiro,Aramaki, Yoshio,Yamamoto, Mitsuo,Kobayashi, Toshitake,Fukumoto, Shoji,Toyoda, Yukio,Henta, Tsutomu,Hata, Akito,Ikeda, Shota,Kaneko, Manami,Hoffman, Isaac D.,Sang, Bi-Ching,Zou, Hua,Kawamoto, Tetsuji
, p. 6942 - 6990 (2017/09/07)
A novel class of therapeutic drug candidates for heart failure, highly potent and selective GRK2 inhibitors, exhibit potentiation of β-adrenergic signaling in vitro studies. Hydrazone derivative 5 and 1,2,4-triazole derivative 24a were identified as hit compounds by HTS. New scaffold generation and SAR studies of all parts resulted in a 4-methyl-1,2,4-triazole derivative with an N-benzylcarboxamide moiety with highly potent activity toward GRK2 and selectivity over other kinases. In terms of subtype selectivity, these compounds showed enough selectivity against GRK1, 5, 6, and 7 with almost equipotent inhibition to GRK3. Our medicinal chemistry efforts led to the discovery of 115h (GRK2 IC50 = 18 nM), which was obtained the cocrystal structure with human GRK2 and an inhibitor of GRK2 that potentiates β-adrenergic receptor (βAR)-mediated cAMP accumulation and prevents internalization of βARs in β2AR-expressing HEK293 cells treated with isoproterenol. Therefore, 115h appears to be a novel class of therapeutic for heart failure treatment.
SUBSTITUTED 2- AMIDOQUINAZOL-4-ONES AS MATRIX METALLOPROTEINASE-13 INHIBITORS
-
Paragraph 1612-1614, (2015/12/23)
The present invention provides a novel amide derivative having a matrix metalloproteinase inhibitory activity, and useful as a pharmaceutical agent, which is a compound represented by the formula (I) wherein ring A is an optionally substituted, nitrogen containing heterocycle, ring B is an optionally substituted monocyclic homocycle or an optionally substituted monocyclic heterocycle, Z is N or NR1 (R1 is a hydrogen atom or an optionally substituted hydrocarbon group), is a single bond or a double bond, R2 is a hydrogen atom or an optionally substituted hydrocarbon group, X is an optionally substituted spacer having 1 to 6 atoms, ring C is (1) an optionally substituted homocycle or (2) an optionally substituted heterocycle other than a ring represented by (II) (X′ is S, O, SO, or CH2), and at least one of ring B and ring C has substituent(s), provided that N-{(1S,2R)-1-(3,5-difluorobenzyl)-3-[(3-ethylbenzyl)amino]2 hydroxypropyl}5,6 dimethyl 4 oxo 1,4 dihydrothieno[2,3-d]pyrimidine-2-carboxamide is excluded, or a salt thereof.
AZA-BENZOFURANYL COMPOUNDS AND METHODS OF USE
-
Page/Page column 67, (2008/06/13)
The invention relates to azabenzofuranyl compounds of Formula (I) with anti-cancer and/or anti-inflammatory activity and more specifically to azabenzofuranyl compounds which inhibit MEK kinase activity. The invention provides compositions and methods useful for inhibiting abnormal cell growth or treating a hyperproliferative disorder, or treating an inflammatory disease in a mammal. The invention also relates to methods of using the compounds for in vitro, in situ, and in vivo diagnosis or treatment of mammalian cells, or associated pathological conditions.
PIPERIDINE DERIVATIVES AND METHODS OF USE THEREOF
-
Page/Page column 95, (2008/12/08)
The present invention relates to Compounds of Formula (I), compositions comprising the compounds, and methods of using the compounds to treat or prevent pain, diabetes, a diabetic complication, impaired glucose tolerance (IGT) or impaired fasting glucose (IFG) in a patient.
