209860-88-8

Basic information

• Product Name: 9ALPHA,11ALPHA-DIHYDROXY-15,15-DIFLUORO-16-PHENOXY-17,18,19,20-TETRANOR-PROSTA-5Z,13E-DIEN-1-OIC ACID
• Synonyms: 9ALPHA,11ALPHA-DIHYDROXY-15,15-DIFLUORO-16-PHENOXY-17,18,19,20-TETRANOR-PROSTA-5Z,13E-DIEN-1-OIC ACID;AFP-172;TAFLUPROST (FREE ACID);tafluprost acid;7-[2-(3,3-difluoro-4-phenoxybut-1-enyl)-3,5-dihydroxycyclopentyl]hept-5-enoic acid;9ALPHA,11ALPHA-DIHYDROXY-15,15-DIFLUORO-16-PHENOXY-17,18,19,20-TETRANOR-PROSTA-5Z,13E-DIEN-1-OIC ACID
• CAS NO: 209860-88-8
• Molecular Formula: C₂₂H₂₈F₂O₅
• Molecular Weight: 410.45
• Mol File: 209860-88-8.mol

Chemical Properties

• Boiling Point: 575.9±50.0 °C(Predicted)
• Appearance: /
• Density: 1.271±0.06 g/cm3(Predicted)
• PKA: 4.76±0.10(Predicted)
• CAS DataBase Reference: 9ALPHA,11ALPHA-DIHYDROXY-15,15-DIFLUORO-16-PHENOXY-17,18,19,20-TETRANOR-PROSTA-5Z,13E-DIEN-1-OIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 9ALPHA,11ALPHA-DIHYDROXY-15,15-DIFLUORO-16-PHENOXY-17,18,19,20-TETRANOR-PROSTA-5Z,13E-DIEN-1-OIC ACID(209860-88-8)
• EPA Substance Registry System: 9ALPHA,11ALPHA-DIHYDROXY-15,15-DIFLUORO-16-PHENOXY-17,18,19,20-TETRANOR-PROSTA-5Z,13E-DIEN-1-OIC ACID(209860-88-8)

Safety Data

• Hazardous Substances Data: 209860-88-8(Hazardous Substances Data)

Usage

Uses

Used in Ophthalmology:
9ALPHA,11ALPHA-DIHYDROXY-15,15-DIFLUORO-16-PHENOXY-17,18,19,20-TETRANOR-PROSTA-5Z,13E-DIEN-1-OIC ACID is used as a therapeutic agent for the treatment of glaucoma. It functions by reducing intraocular pressure, which is a primary risk factor for the development and progression of glaucoma. The unique chemical structure of Tafluprost Acid allows it to be effective in managing this condition, making it a valuable asset in the field of ophthalmology.
Additionally, as the first prostanoid to be released in a preservative-free formula, Tafluprost Acid offers a safer alternative for patients who may be sensitive or allergic to preservatives commonly found in eye drop formulations. This preservative-free aspect enhances patient compliance and reduces the risk of adverse reactions, further solidifying its importance in the treatment of glaucoma.

Upstream product

• 17814-85-6 (4-carboxybutyl)triphenylphosphonium bromide 
• 209861-02-9 (3aR,4R,5R,6aS)-4-((E)-3,3-difluoro-4-phenoxybut-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan-2,5-diol 
• 40665-68-7 dimethyl (3-phenoxy-2-oxopropyl)phosphonate 
• 51638-91-6 (3aR,4R,5R,6aS)-2-oxo-4-((E)-3-oxo-4-phenoxybut-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan-5-yl benzoate 
• 209861-00-7 (3aR,4R,5R,6aS)-4-((E)-3,3-difluoro-4-phenoxybutan-1-en-1-yl)-hexahydro-2-oxo-2H-cyclopenta[b]furan-5-yl benzoate 
• 108-95-2 phenol 
• 53379-98-9 2,2-dimethyl-4-phenoxymethyl-[1,3]dioxolane 
• 538-43-2 3-phenoxy-1,2-propanediol 

Downstream Products

• 1185851-52-8 (5Z)-N-ethyl-7-{(1R,2R,3R,5S)-2-[(1E)-3,3-difluoro-4-(phnoxy)but-1-enyl]-3,5-dihydroxycyclopentyl}hept-5-enamide 
• 209860-87-7 tafluprost 
• 1449413-13-1 C₂₂H₂₈F₂O₅*C₁₂H₂₃N 

Relevant articles and documents

Method for large-scale preparation of tafluprost

The invention discloses a method for industrially preparing tafluprost. The method comprises the following steps: taking Corey lactone as an initial raw material, oxidizing, condensing, fluorinating,deprotecting, reducing, re-condensing, esterifying and r

Method for purifying tafluprost

The purpose of the present invention is to provide a simple and efficient method for purifying tafluprost that can be scaled up in proportion. The present invention relates to the method for purifying tafluprost, which comprises a step for purifying a crude product of tafluprost by silica gel column chromatography and collecting a component containing tafluprost by HPLC analysis. In addition, the present invention also relates to a method for producing tafluprost, which comprises the aforementioned method for purifying tafluprost.

An Asymmetric Suzuki-Miyaura Approach to Prostaglandins: Synthesis of Tafluprost

We report the catalytic asymmetric synthesis of Tafluprost (1), a prostaglandin analogue. This synthesis demonstrates a new approach to prostaglandins involving symmetrization and desymmetrization of a racemic precursor to control the absolute and relative stereochemistry of the cyclopentyl core. Key steps include a diastereo- and enantioselective Rh-catalyzed Suzuki-Miyaura reaction of a racemic bicyclic allyl chloride and an alkenyl boronic acid and a regio- and diastereoselective Pd-catalyzed Tsuji-Trost reaction with an enolate surrogate.

A novel convergent synthesis of the potent antiglaucoma agent tafluprost

Tafluprost (AFP-168, 5) is a unique 15-deoxy-15,15-difluoro-16-phenoxy prostaglandin F2α (PGF2α) analog used as an efficacious ocular hypotensive agent in the treatment of glaucoma and ocular hypertension, as monotherapy, or as adjunctive therapy to β-blockers. A novel convergent synthesis of 5 was developed employing Julia-Lythgoe olefination of the structurally advanced prostaglandin phenylsulfone 16, also successfully applied for manufacturing of pharmaceutical grade latanoprost (2), travoprost (3) and bimatoprost (4), with an aldehyde !-chain synthon 17. The use of the same prostaglandin phenylsulfone 16, as a starting material in parallel syntheses of all commercially available antiglaucoma PGF2α analogs 2-5, significantly reduces manufacturing costs resulting from its synthesis on an industrial scale and development of technological documentation. Another key aspect of the route developed is deoxydifluorination of a trans-13,14-en-15-one 30 with Deoxo-Fluor. Subsequent hydrolysis of protecting groups and final esterification of acid 6 yielded tafluprost (5). The main advantages are the preparation of high purity tafluprost (5) and the application of comparatively cheap reagents. The preparation and identification of two other tafluprost acid derivatives, tafluprost methyl ester (32) and tafluprost ethyl amide (33), are also described.

Processes for the preparation of isomer free prostaglandins

Novel processes for the preparation of a compound of Formula I-2 substantially free of the 5,6-trans isomer: wherein R2, R3 and R4 are as defined in the specification are provided. Novel intermediates for the preparations of isomer free Prostaglandins and derivatives thereof are also provided.

PROCESSES AND INTERMEDIATES FOR THE PREPARATIONS OF ISOMER FREE PROSTAGLANDINS

Novel processes for the preparation of a compound of Formula I-2 substantially free of the 5,6-trans isomer: wherein R2, R3 and R4 are as defined in the specification are provided. Novel intermediates for the preparations of isomer free Prostaglandins and derivatives thereof are also provided.

METHOD OF PURIFICATION OF PROSTAGLANDINS INCLUDING FLUORINE ATOMS BY PREPARATIVE HPLC

The present invention discloses a method of purification of prostaglandins including fluorine atoms by using preparative HPLC. Tafluprost and Travoprost are prostaglandins including fluorine. The chemical structure of the impurities in crude Tafluprost an

AMINE SALTS OF PROSTAGLANDIN ANALOGS

The present application relates to amine salts of prostaglandin analogs and their uses for the preparation of substantially pure prostaglandin analogs. Specific embodiments relate to amine salts of tafluprost and their uses for the preparation of substant

Synthesis and biological properties of novel fluoroprostaglandin derivatives: Highly selective and potent agonists for prostaglandin receptors

Synthesis of novel 7,7-difluoroprostacyclin and 15-deoxy-15,15-difluoro- PGF2α derivatives will be presented. These compounds show high affinity to prostaglandin receptors and potent biological activities.

Synthesis of the highly potent prostanoid FP receptor agonist, AFP-168: A novel 15-deoxy-15,15-difluoroprostaglandin F2α derivative

A novel 15-deoxy-15,15-difluoro-prostaglandin(PG)F2α derivative 6 (AFP-168) has been synthesized from the Corey aldehyde in six steps. A key aspect of this route is difluorination of an enone and a stereoselective Wittig reaction. The compound shows high affinity to the FP receptor and potent activities for an anti-glaucoma agent.