274693-54-8

Basic information

• Product Name: N-[(3aS,4R,6S,6aR)-Tetrahydro-6-(2-hydroxyethoxy)-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl]carbamic acid phenylmethyl ester
• Synonyms: N-[(3aS,4R,6S,6aR)-Tetrahydro-6-(2-hydroxyethoxy)-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl]carbamic acid phenylmethyl ester;CarbaMic acid, [(3aS,4R,6S,6aR)-tetrahydro-6-(2-hydroxyethoxy)-2,2-diMethyl-4H-cyclopenta-1,3-dioxol-4-yl]-, phenylMethyl ester;Ticagrelor Related Compound II;benzyl 6-(2-hydroxyethoxy)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-ylcarbamate
• CAS NO: 274693-54-8
• Molecular Formula: C₁₈H₂₅NO₆
• Molecular Weight: 351.3942
• EINECS: 1533716-785-6
• Mol File: 274693-54-8.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 524.6±50.0 °C(Predicted)
• Appearance: /
• Density: 1.26
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 11.29±0.60(Predicted)
• CAS DataBase Reference: N-[(3aS,4R,6S,6aR)-Tetrahydro-6-(2-hydroxyethoxy)-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl]carbamic acid phenylmethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: N-[(3aS,4R,6S,6aR)-Tetrahydro-6-(2-hydroxyethoxy)-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl]carbamic acid phenylmethyl ester(274693-54-8)
• EPA Substance Registry System: N-[(3aS,4R,6S,6aR)-Tetrahydro-6-(2-hydroxyethoxy)-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl]carbamic acid phenylmethyl ester(274693-54-8)

Safety Data

• Hazardous Substances Data: 274693-54-8(Hazardous Substances Data)

Usage

General Description

N-[(3aS,4R,6S,6aR)-Tetrahydro-6-(2-hydroxyethoxy)-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl]carbamic acid phenylmethyl ester, also known as carprofen, is a nonsteroidal anti-inflammatory drug (NSAID) used in veterinary medicine to relieve pain and reduce inflammation in dogs and cats. It works by inhibiting the production of prostaglandins, which are responsible for causing pain and inflammation in the body. Carprofen is commonly prescribed for the treatment of arthritis, post-operative pain, and other musculoskeletal conditions in pets. It is available in various formulations, including chewable tablets and injectable solutions, and is generally well-tolerated when used according to a veterinarian's instructions. However, like all NSAIDs, carprofen can have potential side effects and should be used with caution in animals with pre-existing kidney, liver, or heart conditions.

Upstream product

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Downstream Products

• 274693-55-9 [3aR-(3aα,4α,6α,6aα)]-2-[[6-amino-2,2-dimethyl tetrahydro-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ethanol 
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• 274693-26-4 [3aR-[3aα,4α,6α,(1R,2S),6aα]]-2-[6-[[[7-(2-(3,4-difluorophenyl)cyclopropyl)]amino-5-(propylthio)-3H-1,2,3-triazolo[4,5-d]pyrimidin-3-yl]tetrahydro-2,2-dimethyl-4H-cyclopenteno-1,3-dioxolan-4-yl]oxy]ethanol 
• 1381841-39-9 2-((1S,2S,3S,4R)-4-(7-(((1R,2S)-2-(3,4-difluorophenyl)cyclopropyl)amino-5-propylthio-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl)-2,3-dihydroxycyclopentyl)oxy)ethyl butyrate 
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• 1402150-24-6 benzyl (1R,2S,3S,4S)-2,3-dihydroxy-4-(2-hydroxyethoxy)-cyclopentylcarbamate 

Relevant articles and documents

Synthesis method of ticagrelor key intermediate

The invention discloses a synthesis method of a ticagrelor key intermediate, which belongs to the technical field of medical technologies, and is technically characterized by comprising the following steps: S1, dissolving a compound I in an organic solvent, adding strong base, reacting with sodium bromoacetate or bromoacetic acid, and adding ethyl chloroformate to synthesize a compound II; S2, adding sodium borohydride into the solution of the compound II in batches to obtain a compound III; and S3, deprotecting the compound III under the action of ammonium formate and 10% palladium on carbon, and then adding Ltartaric acid for salifying to synthesize a compound IV. The invention aims to provide a synthesis method of a ticagrelor key intermediate. The cost is effectively reduced, the synthesis process is simplified, and the method is suitable for large-scale production.

Synthesis and biological evaluation of ticagrelor derivatives as novel antiplatelet agents

Ticagrelor (1) is the first reversible P2Y12 receptor antagonist blocking adenine diphosphate (ADP)-induced platelet aggregation with rapid onset and offset of effects. In this study, synthesis of ticagrelor and its derivatives has been accomplished in a convergent way. The compound design was based on modifications of ticagrelor and its major metabolite (33) in order to ameliorate their pharmacokinetic properties and dosing profile. The final compounds (1a-g, 35a-g) were evaluated for their inhibitory effect on ADP-induced platelet aggregation in rats. The assay results showed that some compounds (e.g., 1b, 1d, 33, 35b, 35f) exhibited comparable potency with that of ticagrelor.

OPTICALLY ACTIVE SALTS OF (3AR,4S,6R,6AS)-6-AMINO-2,2-DIMETHYLTETRAHYDRO-3AH- CYCLOPENTA-[D] [1,3]DIOXOL-4-OL AND A METHOD OF THEIR PREPARATION

Diastereomeric salts of the compound of formula I with D-(-)-mandelic and R-(-)-3- chloromandelic acid, a method of for the preparation thereof and their use in the synthesis of the drug ticagrelor.