1226781-82-3

Basic information

• Product Name: tert-butyl 2-(Methylsulfonyl)-4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate
• Synonyms: tert-butyl 2-(Methylsulfonyl)-4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate;2-(Methylsulfonyl)-2,6-dihydropyrrolo[3,4-c]pyrazole-5(4H)-carboxylic acid tert-butyl ester;tert-butyl 2-methanesulfonyl-2H,4H,5H,6H-pyrrolo[3,4-c]pyrazole-5-carboxylate;MK-3103 Intermediate IV;tert-butyl 2-(methylsulfonyl)-2,6-dihydropyrrolo[3,4-c]pyrazole-5(4H)-carboxylate;Pyrrolo[3,4-c]pyrazole, 2,4,5,6-tetrahydro-2-(methylsulfonyl)-, benzenesulfonate;Omarigliptin Impurity 10;Omarigliptin Intermediate 3
• CAS NO: 1226781-82-3
• Molecular Formula: C₁₁H₁₇N₃O₄S
• Molecular Weight: 287.33538
• EINECS: -0
• Product Categories: Omarigliptin intermediate
• Mol File: 1226781-82-3.mol

Chemical Properties

• Boiling Point: 441.1±55.0 °C(Predicted)
• Appearance: /
• Density: 1.40±0.1 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: -1.95±0.20(Predicted)
• CAS DataBase Reference: tert-butyl 2-(Methylsulfonyl)-4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butyl 2-(Methylsulfonyl)-4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate(1226781-82-3)
• EPA Substance Registry System: tert-butyl 2-(Methylsulfonyl)-4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate(1226781-82-3)

Safety Data

• Hazardous Substances Data: 1226781-82-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Tert-butyl 2-(Methylsulfonyl)-4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate is used as a potential drug candidate for the development of new medications due to its unique chemical structure and potential biological activity. Its ability to modulate protein kinases and act as an anti-inflammatory agent suggests applications in treating various medical conditions, including inflammatory diseases and disorders related to abnormal kinase activity.
Used in Drug Delivery Systems:
In the field of drug delivery, tert-butyl 2-(Methylsulfonyl)-4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate is used as a component in the formulation of pharmaceutical products to improve the stability, solubility, and bioavailability of the active ingredients. Its lipophilic nature and the presence of the tert-butyl group may facilitate the compound's incorporation into various drug delivery systems, such as nanoparticles, liposomes, or solid dispersions, enhancing the therapeutic efficacy and safety of the drug candidates.

Upstream product

• 62773-95-9 N-(2,2-dimethoxyethyl)prop-2-yn 1-amine 
• 157327-42-9 3-(dimethylaminomethylene)-4-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 124-63-0 methanesulfonyl chloride 
• 101385-93-7 3-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 657428-42-7 4,6-dihydro-1H-pyrrolo[3,4-c]pyrazole-5-carboxylic acid tert-butyl ester 
• 6573-19-9 1,4,5,6-tetrahydropyrrolo[3, 4-c]pyrazole 
• 905274-02-4 tert-butyl (3Z)-3-[(dimethylamino)methylene]-4-oxopyrrolidine-1-carboxylate 
• 1280210-79-8 2,6-dihydropyrrole [3,4-c]pyrazole-5(4H)-carboxylic acid tert-butyl ester 

Downstream Products

• 1280210-80-1 2-(methylsulfonyl)-2,4,5,6-tetrahydropyrrolo[3,4-c]pyrazol-5-ium benzenesulfonate 
• 1226781-44-7 Omarigliptin 
• 1226781-87-8 tert-butyl {(2R,3S,5R)-2-(2,5-difluorophenyl)-5-[2-(methylsulfonyl)-2,6-dihydropyrrolo[3,4-c]pyrazol-5(4H)-yl]tetrahydro-2H-pyran-3-yl}carbamate 
• 1226781-80-1 2-methylsulfonic acid-5,6-dihydro-4H-pyrrolo[3,4-c]pyrazole 
• 1280210-98-1 tert-butyl [(2R,3S,5R)-2-(2,5-difiuorophenyl)-5-[2-(methylsulfonyl)-2,6-dihydropyrrolo[3,4-c]pyrazol-5(4H)-yl]-1-{2-[1-(methylsulfonyl)-1H-pyrazol-4-yl]ethyl}piperidin-3-yl]carbamate 
• 1280210-97-0 tert-butyl {(2R,3S,5R)-2-(2,5-difiuorophenyl)-5-[2-(methylsulfonyl)-2,6-dihydropyrrolo[3,4-c]pyrazol-5(4H)-yl]-1-(pyridin-2-ylmethyl)piperidin-3-yl}carbamate 
• 1280210-96-9 tert-butyl {(2R,3S,5R)-2-(2,5-difiuorophenyl)-5-[2-(methylsulfonyl)-2,6-dihydropyrrolo[3,4-c]pyrazol-5(4H)-yl]-1-(pyrazin-2-ylacetyl)piperidin-3-yl}carbamate 
• 1280210-95-8 tert-butyl {(2R,3S,5R)-1-acetyl-2-(2,5-difiuorophenyl)-5-[2-(methylsulfonyl)-2,6-dihydropyrrolo[3,4-c]pyrazol-5(4H)-yl]piperidin-3-yl}carbamate 

Relevant articles and documents

Tetrahydropyranyl amine derivatives used as DPP-IV inhibitors, and a pharmaceutical composition, a preparation and uses of the derivatives

The invention provides tetrahydropyranyl amine derivatives used as DPP-IV inhibitors and having structures shown as a formula I, and a pharmaceutical composition, a preparation and uses of the derivatives. The derivatives have good DPP-IV inhibiting activity, excellent pharmacodynamic performance and lower toxicity. R1, R2, R3, R4, R5, R6, R7, R8, R9, R10 and R11 are hydrogen or deuterium independently and at least comprise a deuterium.

PROCESS FOR THE PREPARATION OF OMARIGLIPTIN

The present invention provides a process for preparing omarigliptin.

Aminopyran ring derivative and its composition and application wherein the dipeptidyl peptidase IV (DPP-IV) inhibitor is used for preparing the drugs for treating metabolic diseases

The present invention relates to an aminopyran ring derivative and its composition and application, specifically speaking, relating to the aminopyran ring derivative represented by the general formula (I) or its stereoisomer, pharmaceutically acceptable salt, prodrug, pharmaceutical composition containing the derivative and the preparation of dipeptidyl peptidase IV (DPP-IV) inhibitor for medical use, wherein the definitions of the substituents in the general formula (I) are the same as those defined in the patent specification.

Amino six member ring derivatives and their use in medicine (by machine translation)

The invention relates to a six-member ring amino derivatives and its application in medicine, specifically relates to the general formula (I) as shown by the six-member ring of the amino derivative or its stereoisomer, pharmaceutically acceptable salt, prodrug, pharmaceutical composition containing the derivative of the dipeptidyl peptidase IV and the preparation (dPP CGI-iV) inhibitors of their medical use, wherein the general formula (I) definition of each substituent in the definition of the description of the same. (by machine translation)

AMINO PYRANOID RING DERIVATIVE AND COMPOSITION AND USE THEREOF

The present invention relates to an amino pyran ring derivative and a composition and use thereof, and in particular, to an amino pyran ring derivative represented by general formula (I) or a stereoisomer, a pharmaceutically acceptable salt or a prodrug thereof, a pharmaceutical composition comprising the derivative, and their medical use in the manufacture of a di-peptidyl peptidase IV (DPP-IV) inhibitor, in formula (I) the substituents are defined the same as those in the specification.

Preparation method for 2-formyl chloride-2,4,5,6-tetrahydropyrrole[3,4-c]pyrazole benzene sulfonate

The invention discloses a preparation method for 2-formyl chloride-2,4,5,6-tetrahydropyrrole[3,4-c]pyrazole benzene sulfonate. The preparation method comprises the following steps: (1) adding a solvent A and dimethyl formamide-dimethyl adipate (DMF-DMA) i

PROCESS FOR PREPARING CHIRAL DIPEPTIDYL PEPTIDASE-IV INHIBITORS

A process for preparing a compound of structural Formula Ia: comprising Boc deprotection with TFA of, reductive amination of:.

Evolution of a Manufacturing Route to Omarigliptin, A Long-Acting DPP-4 Inhibitor for the Treatment of Type 2 Diabetes

Development of a convergent synthesis of omarigliptin (MK-3102) suitable for commercial manufacture is described. The target molecule is assembled through a diastereoselective reductive amination of a highly functionalized pyranone with a mesylated pyrazole followed by deprotection of a Boc group. The synthesis of the pyranone relies on three Ru-catalyzed reactions: (1) a DKR reduction of a rac-α-aminoketone to set the two contiguous stereogenic centers, (2) a cycloisomerization of a bis-homopropargylic alcohol to a dihydropyran, and, finally, (3) a Ru-catalyzed oxidation of a pyranol to the desired pyranone. The regioselective synthesis of a N-Boc-1-mesyl pyrazole fragment was achieved via base-promoted mesyl group isomerization to afford 30:1 selectivity. A highlight of the endgame process development is telescoping a Boc deprotection and reductive amination followed by direct crystallization of the penultimate from the reaction mixture. This avoids handling of an unstable, mutagenic 1-mesylpyrazole BSA salt used in the earlier multikilogram deliveries and improves the overall diastereoselectivity and efficiency of the route.

Crystalline forms of a dipeptidyl peptidase-IV inhibitors

Novel crystalline forms of (2R,3S,5R)-2-(2,5-Difluorophenyl)-5-[2-(methylsulfonyl)-2,6-dihydropyrrolo[3,4-c]pyrazol-5(4H)-yl]tetrahydro-2H-pyran-3-amine are potent inhibitors of dipeptidyl peptidase-IV and are useful for the treatment of non-insulin dependent (Type 2) diabetes mellitus. The invention also relates to pharmaceutical compositions containing these novel forms, processes to prepare these forms and their pharmaceutical compositions as well as uses thereof for the treatment of Type 2 diabetes.

Omarigliptin (MK-3102): A novel long-acting DPP-4 inhibitor for once-weekly treatment of type 2 diabetes

In our effort to discover DPP-4 inhibitors with added benefits over currently commercially available DPP-4 inhibitors, MK-3102 (omarigliptin), was identified as a potent and selective dipeptidyl peptidase 4 (DPP-4) inhibitor with an excellent pharmacokinetic profile amenable for once-weekly human dosing and selected as a clinical development candidate. This manuscript summarizes the mechanism of action, scientific rationale, medicinal chemistry, pharmacokinetic properties, and human efficacy data for omarigliptin, which is currently in phase 3 clinical development.