1061314-04-2

Basic information

• Product Name: Benzoic acid, 5-broMo-2-chloro-4-(Methoxycarbonyl)-
• Synonyms: Benzoic acid, 5-broMo-2-chloro-4-(Methoxycarbonyl)-
• CAS NO: 1061314-04-2
• Molecular Formula: C₉H₆BrClO₄
• Molecular Weight: 293.49854
• Mol File: 1061314-04-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Benzoic acid, 5-broMo-2-chloro-4-(Methoxycarbonyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzoic acid, 5-broMo-2-chloro-4-(Methoxycarbonyl)-(1061314-04-2)
• EPA Substance Registry System: Benzoic acid, 5-broMo-2-chloro-4-(Methoxycarbonyl)-(1061314-04-2)

Safety Data

• Hazardous Substances Data: 1061314-04-2(Hazardous Substances Data)

Upstream product

• 1426923-27-4 C₈H₆BrClO₂ 
• 7697-27-0 2-bromo-4-methylbenzoic acid 
• 2458-12-0 3-amino-p-toluic acid 
• 1061314-02-0 2-bromo-5-chloro-4-methyl-benzoic acid methyl ester 

Downstream Products

• 1204305-48-5 C₉H₅BrCl₂O₃ 
• 1061314-08-6 1-(allyloxymethyl)-2-bromo-5-chloro-4-(4-ethylbenzyl)-benzene 
• 1061314-20-2 (2S,3S,4R,5R,6R)-2-(2-(allyloxymethyl)-4-chloro-5-(4-ethylbenzyl)phenyl)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran 
• 1061314-50-8 (5-chloro-4-(4-ethylbenzyl)-2-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)-phenyl)methanol 
• 1204220-87-0 5-chloro-4-(4-ethylbenzyl)-2-[(2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl]benzoic acid 
• 1427370-50-0 (2R,3S,4S,4aR,10bS)-8-chloro-9-(4-ethylbenzyl)-3,4-dihydroxy-2-(hydroxymethyl)-3,4,4a,10b-tetrahydropyrano[3,2-c][2]benzopyran-6(2H)-one 
• 1355218-46-0 2-bromo-5-chloro-4-(4-ethoxybenzyl)benzoic acid methyl ester 
• 1061315-24-9 (2-bromo-5-chloro-4-(4-ethoxybenzyl)phenyl)methanol 
• 1427370-46-4 1-(allyloxymethyl)-2-bromo-5-chloro-4-(4-ethoxybenzyl)benzene 
• 1427370-47-5 (2S,3S,4R,5R,6R)-2-[2-(allyloxymethyl)-4-chloro-5-(4-ethoxybenzyl)phenyl]-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran 
• 1204220-95-0 5-chloro-4-(4-ethoxybenzyl)-2-[(2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl]benzenemethanol 
• 1427370-48-6 5-chloro-4-(4-ethoxybenzyl)-2-[(2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl]benzoic acid 
• 1427370-49-7 (2R,3S,4S,4aR,10bS)-8-chloro-9-(4-ethoxybenzyl)-3,4-dihydroxy-2-(hydroxymethyl)-3,4,4a,10b-tetrahydropyrano[3,2-c][2]benzopyran-6(2H)-one 
• 1061314-05-3 2-bromo-5-chloro-4-(4-ethylbenzoyl)benzoic acid methyl ester 

Relevant articles and documents

A new and improved process for C-aryl glucoside SGLT2 inhibitors

A practical and scalable synthesis of C-glycosides identified as highly potent sodium-dependent glucose transporter 2 (SGLT2) inhibitors is described. Highlights of the synthetic process are a concise, ten-step synthesis of a structurally complex active pharmaceutical ingredient from a known intermediate via a selective and quantitative addition of an aryl species to the Weinreb amide, and the isomers of undesired ortho-products were avoided during the preparation. The chemistry developed has been applied to prepare SGLT2 inhibitors without recourse to chromatography.

Improved preparation of (1S,3′R,4′S,5′S,6′R)-5- chloro-6-[(4-ethylphenyl)methyl]-3′,4′,5′,6′-tetrahydro- 6′-(hydroxymethyl)-spiro[isobenzofuran-1(3H),2′-[2H]pyran]-3′, 4′,5′-triol

A convenient approach for the preparation of (1S,3′R,4′S, 5′S,6′R)-5-chloro-6-[(4-ethylphenyl)methyl]-3′,4′, 5′,6′-tetrahydro-6′-(hydroxymethyl)-spiro[isobenzofuran-1(3H), 2′-[2H]pyran]-3′,4′,5′-triol is developed. The targeted compound was synthesized from 2-bromo-4-methylbenzoic acid in nine steps and the isomers of undesired ortho-products were avoided during the preparation.

Pyrano[3,2-c]benzopyran-6(2h)-one derivatives and uses thereof

The present invention relates to new pyrano[3,2-c]benzopyran-6(2H)-one derivatives that act as SGLT2 inhibitors, which makes them promising candidates for the treatment of diabetes and other diseases and conditions mediated by SGLT2. These new drugs also exhibit platelet aggregation inhibitory activity which makes them promising candidates in the treatment and/or prevention of prothrombotic conditions. The invention also relates to the use of such pyrano[3,2-c]benzopyran-6(2H)-one derivatives in the treatment or prevention of the diabetes and other disorders and conditions mediated by SGLT2, as a single active ingredient or in combination with another antidiabetic agent or a drug for the treatment of hypertension, chronic heart failure or atherosclerosis, and pharmaceutical compositions comprising said new pyrano[3,2-c]benzopyran-6(2H)-one derivatives.

PYRANO[3,2-c][2]BENZOPYRAN-6(2H)-ONE DERIVATIVES AND USES THEREOF

The present invention relates to new pyrano[3,2-c][2]benzopyran-6(2H)-one derivatives that act as SGLT2 inhibitors, which makes them promising candidates for the treatment of diabetes and other diseases and conditions mediated by SGLT2. These new drugs also exhibit platelet aggregation inhibitory activity which makes them promising candidates in the treatment and/or prevention of prothrombotic conditions. The invention also relates to the use of such pyrano[3,2-c][2]benzopyran-6(2W)-one derivatives in the treatment or prevention of the diabetes and other disorders and conditions mediated by SGLT2, as a single active ingredient or in combination with another antidiabetic agent or a drug for the treatment of hypertension, chronic heart failure or atherosclerosis, and pharmaceutical compositions comprising said new pyrano[3,2-c][2]benzopyran-6(2H)-one derivatives.

Conformationally constrained spiro C-arylglucosides as potent and selective renal sodium-dependent glucose co-transporter 2 (SGLT2) inhibitors

(Chemical Equation Presented) Sodium glucose co-transporter 2 (SGLT2) is an emerging target for the treatment of type 2 diabetes mellitus (DM2). Here, the synthesis and preliminary biological evaluation of a series of potent, selective SGLT2 inhibitors, derived from a rigid spiro C-arylglucoside scaffold, is described.

Exploration of O-spiroketal C-arylglucosides as novel and selective renal sodium-dependent glucose co-transporter 2 (SGLT2) inhibitors

A series of novel O-spiroketal C-arylglucosides have been prepared and evaluated in cell-based functional assays for activity against human sodium-dependent glucose co-transporters 1 and 2 (SGLT1 and 2). The core spiro[isobenzofuran-1,2′-pyran] structure proved to be an effective scaffold for diversification and a number of compounds with single digit nanomolar potency and high selectivity have been synthesized. Compound 5a promoted glucosuria when administered in vivo in rats and produced a significant blood glucose reduction effect.

O-Spiro C-aryl glucosides as novel sodium-dependent glucose co-transporter 2 (SGLT2) inhibitors

Two series of O-spiro C-aryl glucosides were synthesized and tested for inhibition of hSGLT1 and hSGLT2. 6′-O-Spiro C-aryl glucosides exhibited potent in vitro hSGLT2 inhibitory activity but 2′-O-spiro C-aryl glucosides showed no in vitro hSGLT2 inhibitory activity at a screening concentration of 1 μM.

BENZYLIC GLYCOSIDE DERIVATIVES AND METHODS OF USE

Provided are compounds having an inhibitory effect on sodium-dependent glucose cotransporter SGLT. The invention also provides pharmaceutical compositions, methods of preparing the compounds, synthetic intermediates, and methods of using the compounds, independently or in combination with other therapeutic agents, for treating diseases and conditions which are affected by SGLT inhibition.

GLUCOSE TRANSPORT INHIBITORS AND METHODS OF USE

Provided are compounds having an inhibitory effect on sodium-dependent glucose cotransporter SGLT. The invention also provides pharmaceutical compositions, methods of preparing the compounds, synthetic intermediates, and methods of using the compounds, independently or in combination with other therapeutic agents, for treating diseases and conditions which are affected by SGLT inhibition.