- An improved synthesis of latanoprost involving effective control on 15(S) diastereomer
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An improved process for the synthesis of latanoprost having excellent optical purity (de 99.9%, [α]D20 = +35.37° (c = 0.90, acetonitrile)) without use of preparative HPLC is described. This process involves effective purification of hydroxyl intermediate (5A) through solvent crystallization followed by inhibition of inversion of the chiral center at C-15 position. This was possible due to judicious use of diol intermediate (6) for double bond reduction prior to hydroxyl protection.
- Sasane, Sachin A.,Bhise, Nandu B.,Singh, Girij P.,Joseph, Alex,Shenoy, Gautham G.
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p. 2350 - 2356
(2019/07/31)
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- Secondary compounds in the catalytic hydrogenation of enone and allylic alcohol prostaglandin intermediates: Isolation, characterization, and X-ray crystallography
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The discovery of the intraocular pressure reduction of 13,14-hydrogenated prostaglandins, among which Latanoprost is the most used drug in glaucoma treatment, has stimulated researchers to improve the synthesis of prostaglandins and their structural analo
- Tǎnase, Constantin I.,Cocu, Florea,Drǎghici, Constantin,Hanganu, Anamaria,Pintilie, Lucia,Maganu, Maria,Munteanu, Cristian V. A.,Shova, Sergiu
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p. 7582 - 7599
(2019/05/27)
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- Processes for the preparation of isomer free prostaglandins
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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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Paragraph 0147; 0148; 0149; 0150
(2015/03/03)
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- PROCESSES AND INTERMEDIATES FOR THE PREPARATIONS OF ISOMER FREE PROSTAGLANDINS
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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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Paragraph 0147; 0148; 0149; 0150
(2015/02/25)
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- Method for preparing prostaglandin F analogue
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A method for preparing a prostaglandin F analogue represented by the following formula (I) is disclosed, wherein R1, and are as defined in the specification.
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Page/Page column 10-11
(2009/10/21)
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- Method for preparing prostaglandin derivative
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A method for preparing a prostaglandin derivative represented by the following general formula (I): (wherein Ph represents phenyl group, R1 represents a C1-7 alkyl group, a C1-7 alkenyl group, phenyl group, or benzyl group), which comprises the successive steps (1) to (8) described in the specification, or any one step or two or more successive steps selected from the group consisting of the steps (1) to (8). A method for efficiently, inexpensively and safely preparing prostaglandin derivatives, of which typical example is latanoprost, is provided.
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Page/Page column 9
(2008/06/13)
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- METHOD FOR PREPARING PROSTAGLANDIN DERIVATIVE
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A method for preparing a prostaglandin derivative represented by the following general formula (I): (wherein Ph represents phenyl group, R1 represents a C1-7 alkyl group, a C1-7 alkenyl group, phenyl group, or benzyl group), which comprises the successive steps (1) to (8) described in the specification, or any one step or two or more successive steps selected from the group consisting of the steps (1) to (8). A method for efficiently, inexpensively and safely preparing prostaglandin derivatives, of which typical example is latanoprost, is provided.
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Page/Page column 6
(2008/06/13)
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- Method and intermediate for preparing a prostaglandin F-type compound
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A method for preparing a prostaglandin F-type compound. Also disclosed is an intermediate of the following formula (II) compound wherein R′, X and A have the same meaning as given in the specification.
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Page/Page column 13
(2010/10/20)
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