1163135-95-2

Basic information

• Product Name: (5E)-BiMatoprost
• Synonyms: (5E)-BiMatoprost;(5E)-7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenyl-1-penten-1-yl]cyclopentyl]-N-ethyl-5-heptenaMide;5-trans-BiMatoprost;5,6-trans-Bimatoprost;5-trans-17-phenyl trinor Prostaglandin F2.alpha. ethyl amide
• CAS NO: 1163135-95-2
• Molecular Formula: C₂₅H₃₇NO₄
• Molecular Weight: 415.56558
• Product Categories: Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 1163135-95-2.mol

Chemical Properties

• Boiling Point: 629.8±55.0 °C(Predicted)
• Appearance: /
• Density: 1.145±0.06 g/cm3(Predicted)
• Storage Temp.: Amber Vial, -86°C Freezer, Under inert atmosphere
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 14.25±0.20(Predicted)
• Stability: Light Sensitive, Temperature Sensitive
• CAS DataBase Reference: (5E)-BiMatoprost(CAS DataBase Reference)
• NIST Chemistry Reference: (5E)-BiMatoprost(1163135-95-2)
• EPA Substance Registry System: (5E)-BiMatoprost(1163135-95-2)

Safety Data

• Hazardous Substances Data: 1163135-95-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(5E)-BiMatoprost is used as a key intermediate for the production and purification of Bimatoprost (B386800), a medication prescribed for the treatment of glaucoma and ocular hypertension. Its role in the synthesis process is essential for creating a more efficient and effective method of producing Bimatoprost, ultimately benefiting patients suffering from these eye conditions.

Upstream product

• 75-04-7 ethylamine 
• 1163135-94-1 methyl ester of 5-trans-binaprost acid 
• 856240-62-5 (3aR,4R,5R,6aS)-hexahydro-4-[(1E,3S)-3-hydroxy-5-phenyl-1-penten-1-yl]-2H-cyclopenta[b]furan-2,5-diol 

Relevant articles and documents

PROCESS FOR PREPARATION OF PROSTAGLANDIN F2α ANALOGUES

A convergent synthesis of the prostaglandin F2α analogues, travoprost and bimatoprost, was developed employing Julia-Lythgoe olefination of the structurally advanced phenylsulfone with an enantiomerically pure aldehyde ω-chain synthon. The novel convergent strategy allows the synthesis of a whole series of prostaglandin analogues of high purity from a common and structurally advanced prostaglandin intermediate.

A novel convergent synthesis of the antiglaucoma PGF2α analogue bimatoprost

The 17-phenyl PGF2α analogue bimatoprost (10a) is the most efficacious ocular hypotensive agent currently available for the treatment of glaucoma or ocular hypertension. A novel convergent synthesis of 13,14-en-15-ol prostamideF2α an

Bimatoprost crystalline form I

The invention provides a novel polymorphic form I of crystalline bimatoprost, method for preparation thereof and new crystalline intermediates in the preparation. This form I of crystalline bimatoprost is used in purification of crude bimatoprost and in storage of bimatoprost as active pharmaceutical intermediate. Use of the physical form of bimatoprost in the manufacture of a medicament is also disclosed.

PREPARATION OF PROSTAMIDES

The present invention provides a process for the preparation of a prostamide which comprises the steps of (d) reacting first intermediate having the general formula (I) with DIBAL wherein Z is a protecting group and the dotted line represents the presence or absence of a double bond to yield a second intermediate having the general Formula (II) (b) reacting said second intermediate with Na(TMS)2N and (C6H5)3P+(CH2)6CONR2X wherein R is a C1-5 alkyl or hydrogen and X is an anion to yield a third intermediate having the general formula (III) (c) reacting said third intermediate with a protecting agent to yield a fourth intermediate having the general formula IV (e) reacting said fourth intermediate to remove said protecting groups and yield a prostamide having the general formula V