108440-70-6Relevant articles and documents
Synthesis and Optimization of Canagliflozin by Employing Quality by Design (QbD) Principles
Metil, Dattatray S.,Sonawane, Swapnil P.,Pachore, Sharad S.,Mohammad, Aaseef,Dahanukar, Vilas H.,McCormack, Peter J.,Reddy, Ch. Venkatramana,Bandichhor, Rakeshwar
, p. 27 - 39 (2018)
Efforts toward a synthesis and process optimization of canagliflozin 1 are described. Canagliflozin synthesis was accomplished via purified open ring intermediate 12. The process was optimized by employing quality by design (QbD) methodologies, and a telescopic strategy was executed for the first three and last two steps in a total six-step sequence. Optimization of the Friedel-Craft acylation reaction followed by Lewis acid mediated reductive elimination, n-BuLi mediated C-arylation, and reductive demethoxylation was performed to develop a robust process. These steps were found to be critical; therefore, critical process parameters (CPPs) were identified by employing design of experiment (DoE) methodology. In addition, control strategies for dealing with impurities are described.
SYNTHESIS, CRYSTAL STRUCTURE, ANTI-LUNG CANCER ACTIVITY OF 2-(4-FLUOROPHENYL)-5- (5-IODO-2-METHYLBENZYL)THIOPHENE
Dong, Y. L.,Liu, J. P.,Qiu, F.,Wang, C. M.,Zhang, Z. F.,Zhou, L. P.
, p. 1111 - 1116 (2020)
Abstract: New heterocycle compound 2-(4-fluorophenyl)-5-(5-iodo-2-methylbenzyl)thiophene (1), designed using5-iodo-2-methylbenzoic acid (2) as the starting material is successfully obtained via the multiple synthesis route and finally characterized by IR, 1H NMR, and single crystal X-ray crystallography. In addition, the in vitro anticancer activity of compound 1 on three human lung cancer cells (H20, H2227, and H69) is further determined, which suggests that compound 1 may be a potential anticancer agent.
Glucopyranosyl derivative and application thereof
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Paragraph 0260; 0287-0289, (2021/01/24)
The present invention relates to glucopyranosyl derivative and uses thereof. Specifically, the invention relates to a glucopyranosyl derivative used as a sodium-dependent glucose transporter 1(SGLT1)inhibitor and a pharmaceutically acceptable salt or stereoisomer thereof, and further relates to a pharmaceutical composition containing the derivative. The invention also relates to application of thecompound and the pharmaceutical composition thereof in preparation of drugs for treating diabetes and diabetes-related diseases.
Preparation method of carbagliflozin intermediate and application of intermediate in preparation of glipizide
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Paragraph 0043; 0067-0068; 0073-0074; 0079-0080; 0084; ..., (2021/11/26)
The invention provides a preparation method of a carbagliflozin intermediate and an application thereof in preparation of glipizide. To the preparation method, 5 - iodine -2 - methylbenzoic acid and a chlorination reagent are subjected to a Fourier acylation reaction, 5 - iodine -2 - methylbenzoyl chloride is obtained. The 5 -iod -2 -methylbenzoyl chloride and 2 - (4 - fluorophenyl) thiophene were subjected to a Fries alkylation reaction to give (5 -iod -2 -methylphenyl) (5 - (4 - fluorophenyl) thiophene -2 -yl) methyl ketone. (5 -iod -2 -methylphenyl) (5 - (4 - fluorophenyl) thiophene -2 -yl) methyl ketone was subjected to a carbonyl reduction reaction to give a crude product of. The intermediate crude product is subjected to purification treatment to obtain the glipizide intermediate. The preparation method has the advantages of mild reaction conditions, simple operation, environmental protection, safety, suitability for industrial mass production, and high product yield and purity.
GLUCOPYRANOSYL DERIVATIVE AND USE THEREOF
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Paragraph 0242; 0255-0256, (2020/12/16)
The present invention relates to a glucopyranosyl derivative and a use thereof. In particular, the present invention relates to a glucopyranosyl derivative that is used as an inhibitor of sodium-dependent glucose transporters (SGLTs), particularly being used as an inhibitor of sodium-dependent glucose transporter-1 (SGLT1), and a pharmaceutically acceptable salt or stereoisomer thereof, further relating to a pharmaceutical composition containing the derivative. The present invention further relates to a use of the compound and a pharmaceutical composition thereof in the preparation of a drug for treating diabetes and diabetes-related diseases.
N-Heterocyclic Carbene Catalyzed Photoenolization/Diels–Alder Reaction of Acid Fluorides
Agrawal, Arush,G?tze, Jan P.,Golz, Paul,Hopkinson, Matthew N.,Mavroskoufis, Andreas,Rajes, Keerthana,Ru?, Vincent
supporting information, p. 3190 - 3194 (2020/01/24)
The combination of light activation and N-heterocyclic carbene (NHC) organocatalysis has enabled the use of acid fluorides as substrates in a UVA-light-mediated photochemical transformation previously observed only with aromatic aldehydes and ketones. Stoichiometric studies and TD-DFT calculations support a mechanism involving the photoactivation of an ortho-toluoyl azolium intermediate, which exhibits “ketone-like” photochemical reactivity under UVA irradiation. Using this photo-NHC catalysis approach, a novel photoenolization/Diels–Alder (PEDA) process was developed that leads to diverse isochroman-1-one derivatives.
GLUCOPYRANOSYL DERIVATIVE AND USE THEREOF
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Paragraph 00227; 00246, (2019/08/12)
Provided are a glucopyranosyl derivative as a sodium-dependent glucose transporters inhibitor, especially as a SGLT1 inhibitor, a pharmaceutically acceptable salt or a stereoisomer thereof, a pharmaceutical composition thereof, and the uses of the compound and pharmaceutical composition thereof in the preparation of drugs for the treatment of diabetes and diabetes-related diseases.
Process for synthesizing card Geleg only (by machine translation)
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Paragraph 0035; 0043; 0051, (2016/12/01)
The invention discloses a process for synthesizing card Geleg only, in order to 2?Methyl benzoic acid as starting material, use of improvised catalyst, reaction to produce the iodine iodate a in the middle, or in 2?Methyl benzoic acid as starting material, the metal reagent and under the action of catalyst, by adding liquid bromine, synthetic intermediates b; optionally intermediate one or intermediate two acylation reaction with thionyl chloride, to Friedel-crafts reaction produce intermediate three; in order to ALPHA?D?Glucose as raw material, with the reaction protection of all hydroxyl after pivalyl chloride, and then with zinc bromide, trimethyl silane reaction produce intermediate four; three intermediate the intermediate body, connecting delivery into intermediate five; finally under acidic conditions to remove the acyl special fifth heavenly stem, produce the target compound. card Geleg only of the present invention new process for the synthesis of high yield, mild condition, safety and reliability, is suitable for industrial production, raw material is cheap and easy to obtain, it is beneficial to control the production cost. (by machine translation)
A hypoglycemic compound and its preparation method and application
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Paragraph 0132; 0133; 0134, (2017/01/31)
The invention discloses an efficient blood glucose reducing compound as well as a preparation and an application thereof. The structure of the compound disclosed by the invention is shown in a formula I, in the formula, R1, R2, R3 and R4 are defined in specification and claims. The invention further discloses the preparation method of the compound shown in the formula I. The compound shown in the formula I has an inhibiting activity to SGLT (Sodium-Glucose-Linked Transporter), and can be effectively used for preventing or treating diseased related to hyperglycemia.
PROCESS FOR PREPARATION OF CANAGLIFLOZIN
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Paragraph 0190, (2015/12/17)
The present invention relates to a process for the preparation of canagliflozin and intermediates thereof.
