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HETERODIMER COMPOSITIONS AND METHODS FOR THE TREATMENT OF OCULAR DISORDERS
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.
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Paragraph 0441-0442

(2021/11/13)

Asymmetric Synthesis of Corey Lactone and Latanoprost
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.
Hayashi, Yujiro,Umekubo, Nariyoshi
supporting information
p. 6221 - 6227
(2020/09/21)

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.
Zhu, Kejie,Hu, Sha,Liu, Minjie,Peng, Haihui,Chen, Fen-Er
p. 9923 - 9927
(2019/05/16)

High-purity Latanoprost, preparation method therefor and use of Latanoprost
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.
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Paragraph 0098; 0100

(2017/12/01)

Synthesis of prostaglandin analogues, latanoprost and bimatoprost, using organocatalysis via a key bicyclic enal intermediate
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.
Pr??vost, S??bastien,Thai, Karen,Sch??tzenmeister, Nina,Coulthard, Graeme,Erb, William,Aggarwal, Varinder K.
supporting information
p. 504 - 507
(2015/03/05)

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
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(2015/06/17)

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.
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(2015/03/03)

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.
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(2015/02/25)

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).
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(2014/01/08)

PROCESS FOR THE PREPARATION OF PROSTAGLANDIN DERIVATIVES
The invention concerns a new process for the preparation of prostaglandin derivatives, in particular prostaglandin F2α derivatives, for example bimatoprost, latanoprost and travoprost, the new intermediates of said process and their use in the preparation of prostagblandin derivatives.
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Page/Page column 9

(2012/02/01)

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.
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(2012/09/21)

PROCESS FOR THE PURIFICATION OF PROSTAGLANDINS AND ANALOGUES THEREOF
The present invention discloses a process for purification of prostaglandins of formula (1) into enantiomerically pure isomer of formula (2) by reverse phase preparative HPLC, and converting said isomer into prostaglandin derivative of formula (3). The prostaglandin derivative in this invention relates to PGF2α analogues
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Page/Page column 12

(2011/09/14)

PROCESS FOR THE PREPARATION OF PROSTAGLANDIN DERIVATIVES
The invention concerns a new process for the preparation of prostaglandin derivatives, in particular prostaglandin F2α derivatives, for example bimatoprost, latanoprost and travoprost, the new intermediates of said process and their use in the preparation of prostaglandin derivatives.Said process comprises: a) reacting compounds of formula (I) with compounds of formula (II) to give compounds of formula (III) b) reducing with an asymmetric reducing agent the oxo group of the side chain of compounds of formula (III) to give compounds of formula (IV)
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Page/Page column 22

(2010/09/17)

Improved Process for the Production of Prostaglandins and Prostaglandin Analogs
The present invention relates to an improved process for the production of prostaglandins and prostaglandin analogs. In particular, this invention relates to the production of prostaglandins of the PGF2α-series, including latanoprost, travoprost, and bimatoprost, which are active pharmaceutical ingredients used for the reduction of elevated intraocular pressure in patients with glaucoma and ocular hypertension.
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Page/Page column 55

(2010/01/29)

PROSTAGLANDIN ANALOGUES FOR IMPLANT DEVICES AND METHODS
The present invention provides prostaglandins, compositions, and methods useful for sustained release of a therapeutic agent over an extended period of time. Exemplary prostaglandins are C4-C32 alkyl esters or amides of prostaglandins, for example, isobutyl esters and amides.
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Page/Page column 58

(2009/04/25)

A new synthetic approach to high-purity (15R)-latanoprost
This paper describes a new synthesis of latanoprost (1) that afforded high purity latanoprost in 16.9 % overall yield in eight synthetic steps from sulfone 4. The "a chain" in a derivative of the (-)-"Corey lactone" was elongated first, followed by the attachment of a novel, enantiomerically pure "ω chain" synthon. This ensured the absence of the undesired (15S)-1 diastereomer in the synthesized prostaglandin. The crystalline nature of the novel sulfone 4 facilitated its purification. A variation of the new synthesis of latanoprost is described, where the laboratory-scale synthesis was further adapted to a hundred-gram scale. In the course of the present synthesis, a new prostaglandin sulfone intermediate, 21, which may find application in the synthesis of diverse prostaglandin analogs, was introduced. A practical synthesis of novel, enantiomerically pure "ω chain" synthons 15, 16, and 17 has also been carried out, employing diol 12, which was obtained from derivatives of the D-mannitol chiral pool. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.
Martynow, Jacek G.,Jozwik, Julita,Szelejewski, Wieslaw,Achmatowicz, Osman,Kutner, Andrzej,Wisniewski, Krzysztof,Winiarski, Jerzy,Zegrocka-Stendel, Oliwia,Golebiewski, Piotr
p. 689 - 703
(2007/10/03)

Novel intermediate compound for the preparation of prostaglandin F analogue
A method for the preparation of a prostaglandin F analogue presented by the following formula (I): is disclosed, wherein R1, G1, and are as defined in the specification. A novel intermediate compound for the preparation of a prostaglandin F analogue is also disclosed.
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Page/Page column 12-13

(2010/11/27)

PROCESS FOR PREPARATION OF 13,14-DIHYDRO-PGF2α DERIVATIVES
Invention relates to the process for preparation of 13,14-dihydro-PGF2α derivatives of R or S configuration at carbon atom in omega chain substituted by hydroxyl, represented by formula (I), wherein the meaning of substituents is defined in the description. Compounds (I) are valuable biologically active substances or intermediates thereof. The invention especially relates to the process for preparation of 13,14-dihydro-15(R)-17-substituted-18,19,20-trinor-PGF2α, ie. latanoprost.
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Page/Page column 96-99

(2008/06/13)

Process for the synthesis of prostaglandin derivatives
An alternative method for the synthesis of prostaglandin F analogues, in particular, analogues of PGF2α and specifically for the synthesis of latano-prost, wherein the transformation of the lactone intermediate (5) into the corresponding lactol (7) is carried out by treating the lactone intermediate (5) with a silane, preferably polymethylhydrosiloxane (PMHS), in the presence of a titanocene - and preferably titanocene fluoride. The method enables considerable production economies with respect to the conventional reduction of lactone with diisobutylaluminum hydride (DIBAL-H).
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Page/Page column 4; 16; 18-19; 22

(2010/11/24)

Process and intermediates to prepare latanoprost
The present invention is a novel intermediate, compound of the formula (VI) and salts thereof. In addition, the invention includes a process for the preparation of a prostaglandin intermediates compounds (IV) and (XVIII) which comprises (1) contacting a the corresponding enone with (-)-chlorodiisopinocampheylborane while maintaining the reaction mixture temperature in the range of from about ?50° to about 0° and (2) contacting the reaction mixture of step (1) with a boron complexing agent.
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(2008/06/13)

Process and intermediates to prepare latanoprost
The present invention is a novel intermediate, compound of the formula (VI) and salts thereof. In addition, the invention includes a process for the preparation of a 15(S)-prostaglandin intermediates compounds (IV) and (XVIII) which comprises (1) contacting a the corresponding enone with (-)-chlorodiisopinocampheylborane while maintaining the reaction mixture temperature in the range of from about ?50° to about 0° and (2) contacting the reaction mixture of step (1) with a boron complexing agent.
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(2008/06/13)

Phenyl-Substituted Prostaglandins: Potent and Selective Antiglaucoma Agents
A series of phenyl-substituted analoques of prostaglandin F2α (PGF2α) were prepared and evaluated for ocular hypotensive effect and side effects in different animal models.In addition, the activity of the analogues on FP receptors was studied in vitro.The results were compared with those of PGF2α and its isopropyl ester.The phenyl-substituted PGF2α analogues exhibited good intraocular pressure reducing effect, were more selective, and exhibited a much higher therapeutic index in the eye than PGF2α or its isopropyl ester.The analogues exhibited high activity on FP receptors in a stereoselective manner for the 15a-hydroxyl group.
Resul, Bahram,Stjernschantz, Johan,No, Kiyo,Liljebris, Charlotta,Selen, Goeran,et al.
p. 243 - 248
(2007/10/02)