cas 333361-49-2, (5-broMo-2-chloro-phenyl)-(4-ethoxy-phenyl)-Methanone

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GLUCOPYRANOSE DERIVATIVES USEFUL AS SGLT2 INHIBITORS
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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(2020/06/10)

GLUCOPYRANOSE DERIVATIVES USEFUL AS SGLT2 INHIBITORS
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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(2020/06/10)

Combined catalyst for use in specific Friedel-Crafts reactions
The invention provides an application of a ferric trichloride and indium trichloride combined catalyst in a specific Friedel-Crafts reaction, more specifically, the invention provides an application of a ferric trichloride and indium trichloride combined Lewis acid catalyst in preparation of a key intermediate of empagliflozin, dapagliflozin and canagliflozin drugs. Compared with the prior art, the ferric trichloride and indium trichloride combined catalyst provided by the invention can greatly reduce the use of inorganic salt in the preparation process of the key intermediate of the empagliflozin, dapagliflozin and canagliflozin drugs, and obviously reduce the emission of waste water, waste gases and waste residues; and the ferric trichloride and indium trichloride combined catalyst can significantly improve the selectivity of para-position products in the preparation process of the key intermediate of the empagliflozin, dapagliflozin and canagliflozin drugs, can remarkably improve the quality and the yield of a target product, and remarkably reduce the process cost.
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(2020/12/10)

Synthetic method for empagliflozin related substance IMPD
The invention discloses a synthetic method for empagliflozin related substance IMPD. In a current synthetic method of IMPD, a whole synthetic route is longer and the total yield is lower. The synthetic method provided by the invention comprises the following steps: performing hydroxylation by using (2-chloro-5-iodophenyl)(4-fluorophenyl)methanone as a raw material to obtain (2-chloro-5-iodophenyl)(4-hydroxyphenyl)methanone, performing a reaction by using a carbonyl reducing agent to obtain 4-(5-iodo-2-chlorobenzyl)phenol, protecting phenolic hydroxyl groups by using protecting groups such as TBDMS, performing metallization of aromatic iodide by adopting a relatively stable and safe Grignard reagent i-PrMgCl.LiCl, performing methyl glucoside reduction by using a Lewis acid catalyst, and finally performing quenching to obtain the empagliflozin related substance IMPD. The synthetic method provided by the invention has the advantages of an abundant raw material source, a simple, quick andhigh-efficiency reaction, milder reaction conditions, a higher total yield and low costs.
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(2019/07/10)

Processes for the Preparation of SGLT-2 Inhibitors, Intermediates Thereof
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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(2019/01/04)

Carbon glucoside sodium glucose transport protein body 2 inhibitor
The invention relates to a carbon glucoside sodium glucose transport protein body 2 inhibitor, a preparation method and an application of the inhibitor. The carbon glucoside sodium glucose transport protein body 2 inhibitor has a structure as shown in general formula (I) as shown in the specification.
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(2018/07/30)

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.
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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(2017/08/22)

OPTICALLY PURE BENZYL-4-CHLOROPHENYL-C-GLUCOSIDE DERIVATIVE
The present invention belongs to the field of pharmaceutical technology, more specifically relates to optically pure benzyl-4-chlorophenyl-C-glucoside derivatives represented by formulae (II) and (III), a process for preparing these compounds and intermediates thereof, a pharmaceutical formulation and a pharmaceutical composition containing these compounds, and the use of the optically pure benzyl-4-chlorophenyl-C-glucoside derivative as a sodium glucose co-transporter (SGLT) inhibitor in manufacture of a medicament for treating and/or preventing diabetes mellitus (including insulin-dependent diabetes mellitus and non-insulin-dependent diabetes mellitus) or diabetes-associated diseases (including insulin resistance disease and obesity)
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(2015/07/15)

Optically pure benzyl-4-chlorophenyl-C-glucoside derivatives as SGLT inhibitors (diabetes mellitus)
The present invention belongs to the field of pharmaceutical technology, more specifically relates to optically pure benzyl-4-chlorophenyl-C-glucoside derivatives represented by formulae (II) and (III), a process for preparing these compounds and intermediates thereof, a pharmaceutical formulation and a pharmaceutical composition containing these compounds, and the use of the optically pure benzyl-4-chlorophenyl-C-glucoside derivative as a sodium glucose co-transporter (SGLT) inhibitor in manufacture of a medicament for treating and/or preventing diabetes mellitus (including insulin-dependent diabetes mellitus and non-insulin-dependent diabetes mellitus) or diabetes-associated diseases (including insulin resistance disease and obesity) or
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(2015/07/15)

OPTICALLY PURE BENZYL-4-CHLOROPHENYL-C-GLUCOSIDE DERIVATIVE
The present invention relates to a pharmaceutical technology, and more specifically, to optically pure benzyl-4-chloro-phenyl glucoside derivatives represented by the chemical formula II and III or a pharmaceutically acceptable salt thereof. The present invention also relates to a method for preparing the compounds and intermediates thereof, pharmaceutical formulations and pharmaceutical compositions containing the compounds, and the use of the optically pure benzyl-4-chloro-phenyl glucoside derivatives as sodium glucose co-transporter (SGLT) inhibitors for the prevention and treatment of the diabetes including the insulin dependent diabetes mellitus and non-insulin dependent diabetes mellitus and the diabetes-related deseases such as insulin-resistant diseases and obesity.COPYRIGHT KIPO 2015
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(2016/11/24)

Design, synthesis, and biological evaluation of deuterated C-aryl glycoside as a potent and long-acting renal sodium-dependent glucose cotransporter 2 inhibitor for the treatment of type 2 diabetes
SGLT2 inhibitors deuterated at sites susceptible to oxidative metabolism were found to have a slightly longer tmax and half-life (t 1/2), dose-dependent increase in urinary glucose excretion (UGE) in rats, and slightly superior effects on UGE in dogs while retaining similar in vitro inhibitory activities against hSGLT2. In particular, deuterated compound 41 has the potential to be a robust long-acting antidiabetic agent.
Xu, Ge,Lv, Binhua,Roberge, Jacques Y.,Xu, Baihua,Du, Jiyan,Dong, Jiajia,Chen, Yuanwei,Peng, Kun,Zhang, Lili,Tang, Xinxing,Feng, Yan,Xu, Min,Fu, Wei,Zhang, Wenbin,Zhu, Liangcheng,Deng, Zhongping,Sheng, Zelin,Welihinda, Ajith,Sun, Xun
p. 1236 - 1251
(2014/03/21)

(1 S)-1,5-anhydro-1-[5-(4-ethoxybenzyl)-2-methoxy-4-methylphenyl]-1-thio- d -glucitol (TS-071) is a potent, selective sodium-dependent glucose cotransporter 2 (SGLT2) inhibitor for type 2 diabetes treatment
Derivatives of a novel scaffold, C-phenyl 1-thio-d-glucitol, were prepared and evaluated for sodium-dependent glucose cotransporter (SGLT) 2 and SGLT1 inhibition activities. Optimization of substituents on the aromatic rings afforded five compounds with potent and selective SGLT2 inhibition activities. The compounds were evaluated for in vitro human metabolic stability, human serum protein binding (SPB), and Caco-2 permeability. Of them, (1S)-1,5-anhydro-1-[5- (4-ethoxybenzyl)-2-methoxy-4-methylphenyl]-1-thio-d-glucitol (3p) exhibited potent SGLT2 inhibition activity (IC50 = 2.26 nM), with 1650-fold selectivity over SGLT1. Compound 3p showed good metabolic stability toward cryo-preserved human hepatic clearance, lower SPB, and moderate Caco-2 permeability. Since 3p should have acceptable human pharmacokinetics (PK) properties, it could be a clinical candidate for treating type 2 diabetes. We observed that compound 3p exhibits a blood glucose lowering effect, excellent urinary glucose excretion properties, and promising PK profiles in animals. Phase II clinical trials of 3p (TS-071) are currently ongoing.
Kakinuma, Hiroyuki,Oi, Takahiro,Hashimoto-Tsuchiya, Yuko,Arai, Masayuki,Kawakita, Yasunori,Fukasawa, Yoshiki,Iida, Izumi,Hagima, Naoko,Takeuchi, Hiroyuki,Chino, Yukihiro,Asami, Jun,Okumura-Kitajima, Lisa,Io, Fusayo,Yamamoto, Daisuke,Miyata, Noriyuki,Takahashi, Teisuke,Uchida, Saeko,Yamamoto, Koji
experimental part
p. 3247 - 3261
(2010/10/02)

Crystalline forms of 1-chloro-4-(beta-D-glucopyranos-1-yl)-2-[4-ethynyl-benzyl)-benzene, methods for its preparation and the use thereof for preparing medicaments
The invention relates to a crystalline hydrate of 1-chloro-4-(β-D-glucopyranos-1-yl)-2-(4-ethynyl-benzyl)-benzene and to crystalline complexes between 1-chloro-4-(β-D-glucopyranos-1-yl)-2-(4-ethynyl-benzyl)-benzene and a natural amino acid, to methods for the preparation thereof, as well as to uses thereof for preparing medicaments.
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Page/Page column 6

(2010/11/26)

Processes for preparing of glucopyranosyl-substituted (ethynyl-benzyl)-benzene derivatives and intermediates thereof
The present invention relates to processes for preparing the compounds of general formula I, wherein the groups R1, R2 and R3 are defined according to claim 1 and to intermediates of said processes.
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Page/Page column 25

(2010/11/26)

GLUCOPYRANOSYL-SUBSTITUTED BENZONITRILE DERIVATIVES, PHARMACEUTICAL COMPOSITIONS CONTAINING SUCH COMPOUNDS, THEIR USE AND PROCESS FOR THEIR MANUFACTURE
Glucopyranosyl-substituted benzonitrile derivative of formula (I) are disclosed, wherein R3 denotes hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, iso-butyl, tert-butyl, 3-methyl-but-1-yl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, difluoromethyl, trifluoromethyl, pentafluoroethyl, 2-hydroxyl-ethyl, hydroxymethyl, 3-hydroxy-propyl, 2-hydroxy-2-methyl-prop-1 -yl, 3- hydroxy-3-methyl-but-1-yl, 1-hydroxy-1-methyl-ethyl, 2,2,2-trifluoro-1-hydroxy-1-methyl-ethyl, 2,2,2-trifluoro-1-hydroxy-1 -trifluoromethyl-ethyl, 2-methoxy-ethyl, 2-ethoxy-ethyl, hydroxy, methyloxy, ethyloxy, isopropyloxy, difluoromethyloxy, trifluoromethyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, (S)-tetrahydrofuran-3-yloxy, (R)-tetrahydrofuran-3-yloxy, tetrahydropyran-4-yloxy, 1-acetyl-piperidin-4-yloxy, 2-methyloxy-ethyloxy, methylsulfanyl, methylsulfinyl, methylsulfonyl, ethylsulfinyl, ethylsulfonyl, trimethylsilyl and cyano, or a derivative thereof wherein one or more hydroxyl groups of the β-D-glucopyranosyl group are acylated with groups selected from (C1-18-alkyl)carbonyl, (C1-18-alkyl)oxycarbonyl, phenylcarbonyl and phenyl-(C1-3-alkyl)-carbonyl; including tautomers, stereoisomers thereof or mixtures thereof; and physiologically acceptable salts thereof. The compounds according to the invention are suitable for the treatment of metabolic disorders.
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Page/Page column 29

(2008/06/13)

Glucopyranosyl-substituted benzyl-benzene derivatives, medicaments containing such compounds, their use and process for their manufacture
Glucopyranosyloxy-substituted benzyl-benzene derivatives of the general formula I where the groups groups R1, R2, R3a, R3b, R4, R5, R6, X and R7a, R7b, R7c are defined according to claim 1, including the tautomers, the stereoisomers thereof, the mixtures thereof and the salts thereof. The compounds according to the invention are suitable for the treatment of metabolic disorders.
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Page/Page column 12

(2010/11/25)

Glucopyranosyl-substituted ((hetero)cycloalkylethynyl-benzyl)-benzene derivatives, medicaments containing such compounds, their use and process for their manufacture
Glucopyranosyl-substituted ((hetero)cycloalkylethynyl-benzyl)-benzene derivatives of the general formula I where the groups R1 to R6 as well as R7a, R7b, R7c are defined according to claim 1, including the tautomers, the stereoisomers thereof, the mixtures thereof and the salts thereof. The compounds according to the invention are suitable for the treatment of metabolic disorders.
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Page/Page column 15-16

(2010/11/25)

Glucopyranosyl-substituted benzyl-benzene derivatives, medicaments containing such compounds, their use and process for their manufacture
Glucopyranosyl-substituted benzyl-benzene derivatives of the general formula I where the groups R1 to R6 as well as R7a, R7b, R7c are defined according to claim 1, including the tautomers, the stereoisomers thereof, the mixtures thereof and the salts thereof. The compounds according to the invention are suitable for the treatment of metabolic disorders.
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Page/Page column 13-14

(2010/11/26)

Crystalline form of 1-chloro-4-(beta-D-glucopyranos-1-yl)-2-[4-((S)-tetrahydrofuran-3-yloxy)-benzyl]-benzene, a method for its preparation and the use thereof for preparing medicaments
The invention relates to a crystalline form of 1-chloro-4-(β-D-glucopyranos-1-yl)-2-[4-((S)-tetrahydrofuran-3-yloxy)-benzyl]-benzene, to a method for the preparation thereof, as well as to the use thereof for preparing medicaments.
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Page/Page column 4-5

(2010/11/28)

Glucopyranosyl-substituted (heteroaryloxy-benzyl)-benzene derivatives, medicaments containing such compounds, their use and process for their manufacture
Glucopyranosyloxy-substituted (heteroaryloxy-benzyl)-benzene compounds of the general formula I where the groups R1 to R6 as well as R7a, R7b, R7c are defined according to claim 1, including the tautomers, the stereoisomers thereof, the mixtures thereof and the salts thereof. The compounds according to the invention are suitable for the treatment of metabolic disorders.
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Page/Page column 12

(2010/11/24)

CRYSTALLINE FORM OF 1-CHLORO-4-(?-D-GLUCOPYRANOS-1-YL)-2-[4-((S)-TETRAHYDROFURAN-3-YLOXY)-BENZYL]-BENZENE, A METHOD FOR ITS PREPARATION AND THE USE THEREOF FOR PREPARING MEDICAMENTS
The invention relates to a crystalline form of 1-chloro-4-(β-D-glucopyranos-1-yl)-2-[4-((Sj-tetrahydrofuran-3-yloxy)-benzyl]-benzene, to a method for the preparation thereof, as well as to the use thereof for preparing medicaments.
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Page/Page column 12-13

(2010/11/24)

Glucopyranosyl-substituted ((hetero)arylethynyl-benzyl)-benzene derivatives, medicaments containing such compounds, their use and process for their manufacture
Glucopyranosyl-substituted (hetero)arylethynyl-benzene derivatives of the general formula I where the groups R1 to R6 as well as R7a, R7b, R7c are defined according to claim 1, including the tautomers, the stereoisomers thereof, the mixtures thereof and the salts thereof. The compounds according to the invention are suitable for the treatment of metabolic disorders.
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Page/Page column 16

(2008/06/13)

D-xylopyranosyl-substituted phenyl derivatives, medicaments containing such compounds, their use and process for their manufacture
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 13

(2010/02/15)

D-pyranosyl-substituted phenyl derivatives, medicaments containing such compounds, their use and process for their manufacture
D-pyranosyl-substituted phenyls of general formula I [image] 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

(2010/10/20)

Crystalline forms of 1-chloro-4-(beta-D-glucopyranos-1-yl)-2-[4-((R)-tetrahydrofuran-3-yloxy)-benzyl]-benzene, a method for its preparation and the use thereof for preparing medicaments
The invention relates to crystalline forms of 1-chloro-4-(β-D-glucopyranos-1-yl)-2-[4-((R)-tetrahydrofuran-3-yloxy)-benzyl]-benzene, to a method for the preparation thereof, as well as to the use thereof for preparing medicaments.
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Page/Page column 5-6

(2010/11/24)

Processes for preparing of glucopyranosyl-substituted benzyl-benzene derivatives and intermediates therein
The present invention relates to processes for preparing the compounds of general formula I, wherein the groups R1 and R3 are defined according to claim 1. Furthermore this inventions relates to intermediates obtained in these processes.
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Page/Page column 20

(2010/11/24)

Glucopyranosyl-substituted phenyl derivatives, medicaments containing such compounds, their use and process for their manufacture
Glucopyranosyl-substituted benzene derivatives of general formula I where the groups R1 to R6 as well as R7a, R7b, R7c are defined herein and the tautomers, the stereoisomers thereof, the mixtures thereof and the salts thereof. The compounds according to the invention are suitable for the treatment of metabolic disorders.
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Page/Page column 18

(2008/06/13)

GLUCOPYRANOSYL-SUBSTITUTED BENZOL DERIVATIVES, DRUGS CONTAINING SAID COMPOUNDS, THE USE THEREOF AND METHOD FOR THE PRODUCTION THEREOF
The invention relates to glucopyranosyl-substitutedted benzol derivatives of general formula (I), wherein rests R1 to R6 and R7a, R7b, R7c are such as defined in the claim 1, including the tautomers, stereoisomers, mixtures and the salts thereof. The inventive compounds are useful for treating metabolic diseases.
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Page/Page column 46

(2008/06/13)

C-ARYL GLUCOSIDE SGLT2 INHIBITORS AND METHOD
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(2008/06/13)

C-aryl glucoside SGLT2 inhibitors and method
SGLT2 inhibiting compounds are provided having the formula where R1, R2, and R2aare independently hydrogen, OH, OR5, lower alkyl, CF3, OCHF2, OCF3, SR5ior halogen, or two of R1, R2and R2atogether with the carbons to which they are attached can form an annelated five, six or seven membered carbocycle or heterocycle; R3and R4are independently hydrogen, OH, OR5a, OAryl, OCH2Aryl, lower alkyl, cycloalkyl, CF3, —OCHF2, —OCF3, halogen, —CN, —CO2R5b, —CO2H, —COR6b, —CH(OH)R6c, —CH(OR5h)R6d, —CONR6R6a, —NHCOR5c, —NHSO2R5d, —NHSO2Aryl, Aryl, —SR5e, —SOR5f, —SO2R5g, —SO2Aryl, or a five, six or seven membered heterocycle, or R3and R4together with the carbons to which they are attached form an annelated five, six or seven membered carbocycle or heterocycle; R5, R5a, R5b, R5c, R5d, R5e, R5f, R5g, R5hand R5iare independently lower alkyl; R6, R6a, R6b, R6cand R6dare independently hydrogen, alkyl,aryl, alkylaryl or cycloalkyl, or R6and R6atogether with the nitrogen to which they are attached form an annelated five, six or seven membered heterocycle; A is O, S, NH, or (CH2)nwhere n is 0-3. A method is also provided for treating diabetes and related diseases employing an SGLT2 inhibiting amount of the above compound alone or in combination with another antidiabetic agent or other therapeutic agent.
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(2008/06/13)