- Design, synthesis and biological evaluation of nitric oxide releasing derivatives of dapagliflozin as potential anti-diabetic and anti-thrombotic agents
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The cardiovascular complications were highly prevalent in type 2 diabetes mellitus (T2DM), even at the early stage of T2DM or the state of intensive glycemic control. Therefore, there is an urgent need for the intervention of cardiovascular complications in T2DM. Herein, the new hybrids of NO donor and SGLT2 inhibitor were design to achieve dual effects of anti-hyperglycemic and anti-thrombosis. As expected, the preferred hybrid 2 exhibited moderate SGLT2 inhibitory effects and anti-platelet aggregation activities, and its anti-platelet effect mediated by NO was also confirmed in the presence of NO scavenger. Moreover, compound 2 revealed significantly hypoglycemic effects and excretion of urinary glucose during an oral glucose tolerance test in mice. Potent and multifunctional hybrid, such as compound 2, is expected as a potential candidate for the intervention of cardiovascular complications in T2DM.
- Li, Zheng,Xu, Xue,Deng, Liming,Liao, Ruoxian,Liang, Ruiying,Zhang, Bo,Zhang, Luyong
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- GLUCOPYRANOSE DERIVATIVES USEFUL AS SGLT2 INHIBITORS
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The present invention is directed to glucopyranose derivatives of formula (I), pharmaceutical compositions containing them and their use in the treatment of disorders and conditions modulated by SGLT2 activity. More particularly, the compounds of the present invention are useful in the treatment of for example, Type II diabetes mellitus, Syndrome X, and complications and symptoms associated with said disorders.
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- GLUCOPYRANOSE DERIVATIVES USEFUL AS SGLT2 INHIBITORS
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The present invention is directed to glucopyranose derivatives, pharmaceutical compositions containing them and their use in the treatment of disorders and conditions modulated by SGLT2 activity. More particularly, the compounds of the present invention are useful in the treatment of for example, Type II diabetes mellitus, Syndrome X, and complications and symptoms associated with said disorders.
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- Novel preparation process of C-glucoside derivative
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The invention relates to a preparation method of a compound as shown in a formula (VIII), which specifically comprises the following steps: reacting a compound as shown in a formula I with an acylation reagent under the action of an alkaline condition and a catalyst to obtain a compound as shown in a formula II; reacting the compound shown in the formula II with boron trihalide to obtain a compound shown in a formula III; under an alkaline condition, removing a protecting group from the compound shown in the formula III to obtain a compound shown in a formula IV; catalyzing the compound as shown in the formula IV and the compound as shown in the formula V by a phase transfer catalyst under an alkaline condition to obtain a compound as shown in a formula VI; reacting the compound shown in the formula VI with an acylation reagent under an alkaline condition under the action of a catalyst to obtain a compound shown in a formula VII; and under an alkaline condition, removing a protecting group from the compound shown in the formula VII to obtain a compound shown in a formula VIII.
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Paragraph 0101-0103
(2020/12/29)
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- Processes for the Preparation of SGLT-2 Inhibitors, Intermediates Thereof
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The present invention relates to novel, improved processes for the preparation of sodium glucose co-transporter 2 (SGLT-2) inhibitors and novel intermediates thereof. More particularly, the present invention relates to a novel, improved process for the preparation of gliflozin compounds such as empagliflozin and dapagliflozin, intermediates thereof. The product obtained from the processes of present invention may be amorphous or crystalline, or in the form of amorphous/crystalline solid dispersions/solutions with pharmaceutically acceptable polymers and preparation process thereof. Also, the products obtained from the present invention may be used for the preparation of medicaments for the prevention and/or treatment of diseases and conditions associated with SGLT-2 inhibition.
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- A PROCESS FOR THE PREPARATION OF D-GLUCITOL, 1,5-ANHYDRO-1-C-[4-CHLORO-3-[[4- [[(3S)-TETRAHYDRO-3-FURANYL]OXY]PHENYL]METHYL]PHENYL]-, ( 1 S)
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The present invention relates to a process for the preparation of D-glucitol, 1,5- anhydro-1-C-[4-chloro-3-[[ 4-[[(3S)-tetrahydro-3-furanyl)oxy )phenyl] methyl]phenyl]-, (IS) formula-1.
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Page/Page column 17; 18; 19
(2018/09/28)
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- Preparation methods of SGLT-2 diabetes inhibitors and intermediates thereof
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The invention provides a preparation method of an intermediate compound 7 of an SGLT-2 diabetes inhibitor dapagliflozin and an intermediate compound 8 of a SGLT-2 diabetes inhibitor empagliflozin, and new synthesis method of two final products. The preparation method comprises the following steps: carrying out carbonyl group reduction and hydroxyl group protection on a (5-halo-2-chlorophenyl)(4-ethoxyphenyl)ketone compound 1 used as an initial raw material to obtain a Grignard addition reaction key compound 4, and carrying out Grignard addition and acetylation to obtain the compound 7 and the compound 8. The dapagliflozin and the empagliflozin are respectively prepared from the compound 8. The methods have the advantages of simplicity in operation, high yield, high purity of the obtained products, and suitableness for amplified production.
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- THE PRESENT INVENTION RELATES TO PROCESS FOR THE PREPARATION OF D-GLUCITOL, 1,5- ANHYDRO-1-C-[4-CHLORO-3-[[4-[[(3S)-TETRAHYDRO-3-FURANYL] OXY]PHENYL] METHYL]PHENYL]-, (1S) AND ITS CRYSTALLINE FORMS THEREOF.
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The present invention relates to process for the preparation of D-glucitol, 1,5- anhydro-l-C-[4-chloro-3-[[4-[[(3S)-tetrahydro-3-furanyl]oxy]phenyl] methyl]phenyl]-, (1S) formula- 1 and its crystalline forms thereof.
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- C- ARYL GLYCOSID DERIVATIVES, PHARMACEUTICAL COMPOSITION, PREPARATION PROCESS AND USES THEREOF
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This invention relates to a kind of C-aryl glycoside derivatives, its pharmaceutical compositions, preparation methods, and uses thereof. The preparation method comprises: method 1: in a solvent, deprotecting the acetyl protecting groups of compound 1-f in the presence of a base; method 2: 1) compound 2-g reacts with via Mitsunobu reaction; 2) deprotecting the acetyl protecting groups of compound 2-f obtained from step 1; method 3: 1) compound 2-g reacts with via nucleophilic substitution reaction; 2) deprotecting the acetyl protecting groups of compound 3-f obtained from step 1. The pharmaceutical composition comprises a kind of C-aryl glycoside derivatives; it's pharmaceutically acceptable salts and/or prodrugs thereof and excipient thereof. This invention further relates to a kind of C-aryl glycoside derivatives, it's pharmaceutically acceptable salts or pharmaceutical compositions thereof for the use in preparation of a SGLT inhibitor. The C-aryl glycoside derivatives of this invention provides a new direction for the study of SGLT inhibitors.
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Paragraph 0350; 0351; 0352
(2017/04/19)
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- C - aryl glucoside SGLT2 inhibitor
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The invention relates to the field of medicines related to diabetes mellitus and particularly relates to a 2-type sodium-glucose co-transporter (SGLT2) inhibitor with a multi-aryl glucoside structure and shown as the specification, a preparation method thereof, a medicine composition taking the compound as an active components and an application thereof in preparing medicines for resisting diabetes mellitus.
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- NOVEL SGLT INHIBITORS
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The present invention relates to novel compounds of Formula (I), their pharmaceutically acceptable derivatives, tautomeric forms, isomers, polymorphs, prodrugs, metabolites, salts or solvates thereof. The invention also relates to the processes for the sy
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Page/Page column 55
(2013/03/28)
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- ARYL GLYCOSIDE COMPOUND, PREPARATION METHOD AND USE THEREOF
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Disclosed are an aryl glycoside compound as represented by formula I or formular I', a pharmaceutically acceptable salt thereof, optical isomer thereof or a prodrug thereof. The present invention relates to a method of preparing said aryl glycoside compound and the use thereof. The aryl glycoside compound of the present invention has an excellent ability on inhibit SGLT activity, especially SGLT2 activity, and is diabetes-fighting medicine with great potential.
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- ARYL GLYCOSIDE COMPOUND, PREPARATION METHOD AND USE THEREOF
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Disclosed are an aryl glycoside compound as represented by formula I or formular I′, a pharmaceutically acceptable salt thereof, optical isomer thereof or a prodrug thereof. The present invention relates to a method of preparing said aryl glycoside compound and the use thereof The aryl glycoside compound of the present invention has an excellent ability on inhibit SGLT activity, especially SGLT2 activity, and is diabetes-fighting medicine with great potential.
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Paragraph 0131-0135
(2014/01/07)
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- NOVEL SGLT INHIBITORS
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The present invention relates to novel compounds of Formula (I), their pharmaceutically acceptable derivatives, tautomeric forms, isomers, polymorphs, prodrugs, metabolites, salts or solvates thereof. The invention also relates to the processes for the synthesis of novel compounds of Formula (I), their pharmaceutically acceptable derivatives, tautomeric forms, isomers, polymorphs, prodrugs, metabolites, salts or solvates thereof. The present invention also provides pharmaceutical compositions comprising novel compounds of Formula (I) and methods of treating or preventing one or more conditions or diseases that may be regulated or normalized via inhibition of Sodium Glucose Cotransporter-2 (SGLT-2).
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Page/Page column 61
(2013/02/28)
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- GLYCOSIDE DERIVATIVES AND USES THEREOF
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This invention relates to compounds represented by formula (I): wherein the variables are defined as herein above, which are useful for treating diseases and conditions mediated by the sodium D-glucose co-transporter (SGLT), e.g. diabetes. The invention also provides methods of treating such diseases and conditions, and compositions etc. for their treatment
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Page/Page column 116
(2011/05/06)
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- Glycoside Derivatives and Uses Thereof
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This invention relates to compounds represented by formula (I): wherein the variables are defined as herein above, which are useful for treating diseases and conditions mediated by the sodium D-glucose co-transporter (SGLT), e.g. diabetes. The invention also provides methods of treating such diseases and conditions, and compositions etc. for their treatment.
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Page/Page column 56-57
(2011/08/02)
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- D-xylopyranosyl-substituted phenyl derivatives, medicaments containing such compounds, their use and process for their manufacture
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A D-Xylopyranosyl-substituted phenyl compound of general formula I wherein the groups R1 to R5, X, Z and R7a, R7b, R7c are defined as in claim 1, have an inhibiting effect on the sodium-dependent glucose cotransporter SGLT. The present invention also relates to pharmaceutical compositions for the treatment of metabolic disorders.
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Page/Page column 15-16
(2010/02/15)
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