41639-83-2Relevant articles and documents
HETERODIMER COMPOSITIONS AND METHODS FOR THE TREATMENT OF OCULAR DISORDERS
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Paragraph 0441-0442, (2021/11/13)
Described herein are processable compositions comprising at least one moiety that is processable in its free form. Also described herein are compositions and methods for the treatment of ocular diseases or disorders including glaucoma, blepharitis, ocular inflammation, diabetic macular edema, posterior inflammation, anterior inflammation, macular degeneration (e.g., wet macular degeneration (AMD) or dry AMD), post-cataract surgery, and retinal vein occlusion. Said compositions and methods comprise steroids and prostaglandins which demonstrate anti-inflammatory activity, intraocular pressure (IOP) lowering, and/or other desirable activities. Injection of said compositions in the eye provides therapeutic benefit to patients suffering from ocular disorders.
Asymmetric Synthesis of Corey Lactone and Latanoprost
Hayashi, Yujiro,Umekubo, Nariyoshi
supporting information, p. 6221 - 6227 (2020/09/21)
Corey lactone was synthesized in a single pot within 152 minutes in a 50 % overall yield via pot and time economical manner. Latanoprost, an antiglaucoma blockbuster drug, was also synthesized via seven pot reaction with five purifications in a 25 % total yield. One of the key reactions is asymmetric domino Michael/Michael reaction, formal [3+2] cycloaddition reaction, of 3-(dimethylphenylsilyl)propenal and ethyl 4-oxo-2-pentenoate, catalyzed by diphenylprolinol silyl ether, which constructed the core substituted cyclopentanone derivative with nearly optically pure form.
Access to a Key Building Block for the Prostaglandin Family via Stereocontrolled Organocatalytic Baeyer–Villiger Oxidation
Zhu, Kejie,Hu, Sha,Liu, Minjie,Peng, Haihui,Chen, Fen-Er
, p. 9923 - 9927 (2019/05/16)
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.
High-purity Latanoprost, preparation method therefor and use of Latanoprost
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Paragraph 0092; 0093, (2017/12/01)
The invention discloses high-purity Latanoprost, a preparation method therefor and use of the Latanoprost. According to the high-purity Latanoprost disclosed by the invention, the content of an impurity with a structure represented by a formula II shown in the description in the high-purity Latanoprost is not higher than 0.1%. The preparation method comprises the steps: (1) subjecting a compound represented by a formula IV shown in the description (an intermediate 1 of the Latanoprost) to a wittig reaction, so as to obtain a compound represented by a formula V shown in the description (an intermediate 2 of the Latanoprost); (2) subjecting the compound V to washing and purifying by a ammonium chloride solution, then, carrying out dehydroxylation protection or not, and carrying out a reaction with iodo-isopropane, so as to obtain a crude raw pharmaceutical material of the Latanoprost; and (3) loading a sample of the raw pharmaceutical material of the Latanoprost to a silica-gel column, carrying out eluting with an eluate, and carrying out chromatographic purification, thereby obtaining the high-purity Latanoprost.
Compound And Method
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, (2015/06/17)
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
Synthesis of prostaglandin analogues, latanoprost and bimatoprost, using organocatalysis via a key bicyclic enal intermediate
Pr??vost, S??bastien,Thai, Karen,Sch??tzenmeister, Nina,Coulthard, Graeme,Erb, William,Aggarwal, Varinder K.
, p. 504 - 507 (2015/03/05)
Two antiglaucoma drugs, bimatoprost and latanoprost, which are analogues of the prostaglandin, PGF2?±, have been synthesized in just 7 and 8 steps, respectively. The syntheses employ an organocatalytic aldol reaction that converts succinaldehyde into a key bicyclic enal intermediate, which is primed for attachment of the required lower and upper side chains. By utilizing the crystalline lactone, the drug molecules were prepared in >99% ee.
Processes for the preparation of isomer free prostaglandins
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, (2015/03/03)
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
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, (2015/02/25)
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.
COMPOUND AND METHOD
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, (2014/01/08)
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).
Process for the synthesis of prostaglandins and intermediates thereof
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, (2012/09/21)
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.
