856240-62-5

Usage

Uses

Used in Pharmaceutical Industry:
CHEMPACIFIC 59929 is used as an impurity in the synthesis of bimatoprost (B386800) for its role as an antiglaucoma drug and prostaglandin analog. It is important to monitor and control the levels of this impurity to ensure the safety and efficacy of the final product.

Upstream product

• 55076-60-3 (3aR,4R,5R,6aS)-2-oxo-4-((1E)-3-oxo-5-phenylpent-1-en-1-yl)-hexahydro-2H-cyclopenta[b]furan-5-yl benzoate 
• 55444-68-3 (3aR,4R,5R,6aS)-4-[(1E,3S)-3-hydroxy-5-phenylpent-1-en-1-yl]-2-oxo-hexahydro-2H-cyclopenta[b]furan-5-yl benzoate 
• 2550-26-7 4-Phenyl-2-butanone 
• 40601-45-4 diethyl (2-oxo-4-phenylbutyl)phosphonate 
• 31984-10-8 1-bromo-4-phenylbutan-2-one 
• 933789-26-5 (3aR,4R,5R,6aS)-5-hydroxy-4-((E)-3-oxo-5-phenylpent-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan-2-one 
• 62961-72-2 Corey aldehyde 
• 87422-39-7 (3aR,6aS)-3,3-dichloro-3,3a,6,6a-tetrahydro-2H-cyclopenta[b]furan-2-one 
• 542-92-7 cyclopenta-1,3-diene 
• 26054-46-6 (-)-(1S,5R)-2-oxabicyclo[3.3.0]oct-6-en-3-one 
• 5307-99-3 (+/-)-7,7-dichlorobicyclo[3.2.0]hept-2-en-6-one 
• 329313-36-2 (S)-tert-butyldimethyl(5-phenylpent-1-yn-3-yloxy)silane 
• 183904-28-1 (S)-5-phenyl-1-pentyn-3-ol 
• 895153-53-4 (S)-5-phenyl-1-(triisopropylsilyl)pent-1-yn-3-ol 

Downstream Products

• 38344-08-0 (5Z)-bimatoprost acid 
• 155206-00-1 bimatoprost 
• 352276-28-9 (1S,5R,6R,7R)-6-<(3S)-3-hydroxy-5-phenyl-1-pentyl>-7(R)-hydroxy-2-oxabicyclo<3.3.0>octan-3-ol 
• 41639-83-2 latanoprost acid 
• 130209-82-4 latanoprost 
• 1415394-05-6 7-[3,5-dihydroxy-2-(3-hydroxy-5-phenylpent-1-enyl)-cyclopentyl]-5-heptenoic acid (2,5-dioxopyrrolidin-1-yl) ester 
• 1415394-10-3 7-[3,5-dihydroxy-2-(3-hydroxy-5-phenylpent-1-enyl)-cyclopentyl]-5-heptenoic acid 1,3-dioxo-1,3-dihydroisoindol-2-yl ester 
• 1163135-95-2 (5E)-N-ethyl-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenyl-1-pentenyl]-cyclopentyl]hept-5-enamide 

Relevant academic research and scientific papers

Preparation method of bemeprost

The invention discloses a preparation method of bemeprost, which comprises the following steps: (1) in a first solvent, carrying out oxidation reaction on a compound 1 in an oxidation system to generate a compound 2; (2) in a second solvent, under the action of alkali, mixing the compound 2 with a compound 7 for reaction to generate a compound 3; (3) carrying out reduction reaction on the compound3 in a third solvent under the action of a first reducing agent to generate a compound 4; (4) in a fourth solvent, carrying out reduction reaction on the compound 4 under the action of a second reducing agent to generate a compound 5; and (5) in a fifth solvent, under the action of alkali, carrying out the following reaction on the compound 5 and the compound 8 to generate bemeprost of a compound6. According to the preparation method disclosed by the invention, the operation steps are remarkably simplified, the reaction conditions are mild, and the operation is simple and convenient; raw materials are cheap and easy to obtain, and cost is reduced; the product yield is high, and the method is suitable for industrial production.

Access to a Key Building Block for the Prostaglandin Family via Stereocontrolled Organocatalytic Baeyer–Villiger Oxidation

A new protocol for the construction of a crucial bicyclic lactone of prostaglandins using a stereocontrolled organocatalytic Baeyer–Villiger (B-V) oxidation was developed. The key B-V oxidation of a racemic cyclobutanone derivative with aqueous hydrogen peroxide has enabled an early-stage construction of a bicyclic lactone skeleton in high enantiomeric excess (up to 95 %). The generated bicyclic lactone is fully primed with two desired stereocenters and enabled the synthesis of the entire family of prostaglandins according to Corey′s route. Furthermore, the reactivity and enantioselectivity of B-V oxidation of racemic bicyclic cyclobutanones were evaluated and 90–99 % ee was obtained, representing one of the most efficient routes to chiral lactones. This study further facilitates the synthesis of prostaglandins and chiral lactone-containing natural products to promote drug discovery.

Novel method for preparing Prostaglandin derivatives

Provided is a novel method for preparing prostaglandin derivatives. The method is suitable for mass production by effectively manufacturing prostaglandin derivatives with high yield. The method comprises the following steps: (S-1) adding a first reducing agent to a prostaglandin intermediate compound represented by chemical formula II and manufacturing a compound represented by chemical formula III; (S-2) manufacturing a compound represented by chemical formula IV from the compound represented by chemical formula III in the presence of a base; (S-3) adding a second reducing agent to the compound represented by chemical formula IV and manufacturing a compound represented by chemical formula V; and (S-4) performing Wittig reaction of the compound represented by chemical formula V and a compound represented by chemical formula VI, and manufacturing a compound represented by chemical formula I.COPYRIGHT KIPO 2017

Compound And Method

A compound of formula (I): (I) wherein Y is, Z is OR10, NR11R11 SR11, S(0)R11 S02R11, R10 is H, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted heterocyclyl, CO—R11, or a protecting group, and R11 is optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted heterocyclyl, or alkoxyl; a process for making a compound of formula (I); and a process for making a prostaglandin or a prostaglandin analogue using a compound of formula (I). wherein Y is

NOVEL PROCESSES FOR THE PREPARATION OF PROSTAGLANDIN AMIDES

The subject of the invention is process for the preparation of the prostaglandin amides of the general formula I, where in the formula the bonds marked with dotted lines may be single or double bonds, in the case of double bounds at positions 5,6 and 13,14 they may be in cis or in trans orientation, Q stands for a hydroxyl-group and Z stands for a hydroxyl- or oxo-group, R1 and R2 independently represent hydrogen atom or a straight or branched C1-10 alkyl- or aralkyl- group, optionally substituted with —ONO2 group, or an aralkyl- or aryl- group, which contains heteroatom, R3 represents a straight or branched, saturated or unsaturated C4-6 hydrocarbon group, or a C4-10 alkylcycloalkyl- or cycloalkyl- group, or an optionally with alkyl group or halogen atom substituted phenyl-, C7-10 alkylaryl- or hetaryl- group, Y represents (CH2), group or 0 atom or S atom, and where n=0-3.

COMPOUND AND METHOD

A compound of formula (I): (I) wherein Y is, Z is OR10, NR11R11 SR11, S(0)R11 S02R11, R10 is H, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted heterocyclyl, CO-R11, or a protecting group, and R11 is optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted heterocyclyl, or alkoxyl; a process for making a compound of formula (I); and a process for making a prostaglandin or a prostaglandin analogue using a compound of formula (I).

NOVEL PROCESSES FOR THE PREPARATION OF PROSTAGLANDIN AMIDES

The subject of the invention is process for the preparation of the prostaglandin amides of the general formula I, - where in the formula the bonds marked with dotted lines may be single or double bonds, in the case of double bounds at positions 5,6 and 13,14 they may be in cis or in trans orientation, Q stands for a hydroxyl-group and Z stands for a hydroxyl- or oxo-group, R1 and R2 independently represent hydrogen atom or a straight or branched C1-10 alkyl- or aralkyl- group, optionally substituted with -ONO2 group, or an aralkyl- or aryl- group, which contains heteroatom, R3 represents a straight or branched, saturated or unsaturated C4-6 hydrocarbon group, or a C4-10 alkylcycloalkyl- or cycloalkyl- group, or an optionally with alkyl group or halogen atom substituted phenyl-, C7-10 alkylaryl- or hetaryl- group, Y represents (CH2)n group or 0 atom or S atom, and where n=0-3.

Process for the synthesis of prostaglandins and intermediates thereof

A process is disclosed for the preparation of prostaglandins of the PGF2α-series, in particular Latanoprost, Bimatoprost and Travoprost, which are active in the treatment of ocular hypertensive conditions and glaucoma. The invention also relates to novel intermediates involved in the synthesis of these prostaglandin-PGF2α derivatives.

PREPARATION OF PROSTAGLANDIN DERIVATIVES

A process for preparing the prostaglandin derivatives is provided, wherein the benzoyl and p-nitrobenzoyl groups are used as the hydroxyl protective groups. A pharmaceutical composition comprising the prostaglandin derivatives is also provided.

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