- Catalytic Lewis and Br?nsted acid syn-diastereoselective benzylic substitutions of α-hydroxy-β-nitro- and α-hydroxy-β-azido-alkyl arenes
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A series of alkyl and alkenyl p-methoxy arenes containing α,β-disubstituted diamino and amino alcohol groups were synthesized from β-nitro and β-azido benzylic alcohols in the presence of AuCl3 as catalyst. The formation of predominantly syn-disubstituted products were rationalized on the basis of mechanistic considerations and transition state models relying on A1,3-allylic strain. The products could have utility in the design of medicinally relevant compounds and as chiral ligands for asymmetric catalysis. A new synthesis of (+)-sertraline (Zoloft) was achieved.
- Chénard, étienne,Cusson, Jean-Philippe,Hanessian, Stephen,Hensienne, Rapha?l
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p. 292 - 306
(2020/06/17)
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- Chemoenzymatic Synthesis of Sertraline
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A chemoenzymatic approach has been developed for the preparation of sertraline, an established anti-depressant drug. Ketoreductases (KREDs) were employed to yield a key chiral precursor. The bioreduction of the racemic tetralone exhibited excellent enantioselectivity (>99 % ee) and diastereomeric ratio (99:1) at 29 % conversion (the maximum theoretical yield is 50 %) after 7 hours. The resulting (S,S)-alcohol was efficiently oxidized to an enantiopure (S)-ketone, an immediate precursor of sertraline, by using sodium hypochlorite as oxidant and 2-azaadamantane N-oxyl (AZADO) as organocatalyst. Alternative routes aiming at the direct biocatalytic amination using imine reductases and transaminases were unsuccessful.
- Marx, Lisa,Ríos-Lombardía, Nicolás,Süss, Philipp,H?hne, Matthias,Morís, Francisco,González-Sabín, Javier,Berglund, Per
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p. 510 - 513
(2020/01/25)
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- New sertraline analogue, preparation method and applications thereof
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The invention belongs to the technical field of compounds, preparation methods and applications thereof, and specially relates to a sertraline analogue or a pharmaceutically acceptable salt thereof, wherein the sertraline analogue has a structure represented by the following formula (I), and the compound has good pharmaceutical activity compared with sertraline. The invention further provides a preparation method and applications of the compound represented by the formula (I).
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-
Paragraph 0096-0099
(2020/01/12)
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- End-substituted homoallylic amine derivatives, a preparing method thereof and uses of the derivatives
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The invention belongs to the field of chemical medicines, and particularly relates to end-substituted homoallylic amine derivatives, a preparing method thereof and uses of the derivatives. In the method, the end-substituted homoallylic amine derivatives are prepared by allowing a 2-aza-allyl anion to participate, in a high regioselectivity manner, an allylation reaction catalyzed by iridium, and by an intramolecular 2-aza-Cope rearrangement reaction. The derivatives can be synthesized efficiently by the method. The method is simple, convenient and feasible. Prepared compounds have extremely high optical purity. The derivatives prepared by the method can be used for preparing Sertraline and Tametraline which are anti-depression medicines and some natural products.
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- DIPHENYLOXIRANES, PROCESS FOR PREPARATION THEREOF, AND ITS USE IN AN ENANTIOSELECTIVE SYNTHESIS OF (+)-SERTRALINE
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The present invention discloses substituted diphenyloxiranes and process for synthesis thereof. The present invention also provides a process for production of enantiomerically pure anti-3,3'-diphenylmethyloxirane and anti-3,3'-diphenylpropan- 1,2-diol from racemic anti-3,3'-diphenylmethyloxirane using hydrolytic kinetic resolution. Further it provides a process for preparation of enantioselective (+)- Sertraline from anti-3,3'-diphenylpropan-1,2-diol.
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- Concise enantioselective synthesis of (+)-sertraline and (-)-CP-52002 using proline catalysis
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A short enantioselective synthesis of (+)-sertraline and its C4 epimer (-)-CP-52002 with an overall yield of 30%, respectively, as its hydrochloride has been described. The key steps are the proline catalyzed Mannich reaction of acetaldehyde and acid catalyzed intramolecular Friedel-Crafts' alkylation reaction of olefin proceeding with high optical purities.
- Kalshetti, Rupali,Venkataramasubramanian,Kamble, Sanjay,Sudalai, Arumugam
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supporting information
p. 1053 - 1055
(2016/02/16)
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- AN ORGANOCATALYTIC ASYMMETRIC SYNTHESIS OF ANTIDEPRESSANTS
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The present invention relates to a short enantioselective synthesis of 1-amino aryl tetraline compounds of Formula 1 via nucleophilic enamine catalysis using organocatalyst such as proline. wherein R1 and R2 represent independent of each other hydrogen, (un)substituted or substituted amine; R3 and R4 represent independent of each other hydrogen or halogen.
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- Stereoselective amination of chiral benzylic ethers using chlorosulfonyl isocyanate: Total synthesis of (+)-Sertraline
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The stereoselective amination of various chiral benzylic ethers using chlorosulfonyl isocyanate is developed, and the application of this method to the total synthesis of a potent antidepressant, (+)-sertraline, from readily available 1-naphthol is also described (Figure presented).
- Lee, Sang Hwi,Kim, In Su,Li, Qing Ri,Dong, Guang Ri,Jeong, Lak Shin,Jung, Young Hoon
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p. 10011 - 10019
(2012/02/05)
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- Enantioselective syntheses of (+)-sertraline and (+)-indatraline using lithiation/borylation-protodeboronation methodology
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The lithiation/borylation-protodeboronation of a homoallyl carbamate was applied to the synthesis of (+)-sertraline and (+)-indatraline. Due to the presence of the alkene, significant modifications of the methodology were required (use of 12-crown-4, TMSCl, H2O), or a solvent switch to CHCl3, to achieve high yields and high selectivities.
- Roesner, Stefan,Casatejada, Javier Mansilla,Elford, Tim G.,Sonawane, Ravindra P.,Aggarwal, Varinder K.
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p. 5740 - 5743
(2011/12/22)
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- Sertraline racemate and enantiomer: Solid-state characterization, binary phase diagram, and crystal structures
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The racemate and enantiomer of sertraline free base were prepared and characterized. The crystalline sertraline enantiomer is relatively less polymorphic compared with the sertraline-HCl salt. The solid-state nature of sertraline racemate was identified to be a racemic compound through a binary melting point phase diagram and spectroscopy analysis. The crystal structures of the racemate and enantiomer were determined to be monoclinic P121/n1 and P21, respectively.
- He, Quan,Rohani, Sohrab,Zhu, Jesse,Gomaa, Hassan
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experimental part
p. 1633 - 1645
(2011/11/12)
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- Kinetic spectrophotometric methods for the quantitation of sertraline drug in bulk and in formulations
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KINETIC methods (fixed concentration, rate constant and fixed time) for the sensitive and accurate spectrophotometric microdetermination of sertraline basic drug have been described. The methods are based on the reaction between sertraline and iodine in 1,2-dichloroethane as a suitable medium. At a fixed time of 10 min, the spectrum of the formed inner and / or outer-sphere complexes [Drug.I+] I- / and or [DrugI2] is measured at a suitable selected λmax = 396 nm. The concentration of sertraline drug, in its pure form is calculated using the calibration equation for the fixed time method. Beer's law was obeyed in the concentration range of 1.6-48 μg ml -1 and the recovery in average was 99.85%. The relative standard deviation RSD (n = 7) at 8 μg ml-1 is 0.65% and at 24 μg ml-1 is 0.88% within-day , and at 10 μg ml-1 is 0.67% and at 20 μg ml-1 is 0.84% for between-day, respectively. Therefore, the intera- and inter-day RSD values indicated the ruggedness of the fixed time kinetic method. The method is suitable for quantitative determination of sertraline in the concentration range of 6-20 μg ml-1 in pharmaceutical formulation (Lustiral) after its separation as a basic form out of drug formulation additives like starch, glucose,.etc without interference. The results obtained agreed well with the data obtained by an official method. The determination of sertraline by fixed concentration and rate constant methods is feasible with the calibration equations obtained but the fixed time method is more accurate.
- Zayed,El-Habeeb, Abeer A.
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experimental part
p. 463 - 476
(2012/08/08)
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- A RECYCLING PROCESS FOR PREPARING SERTRALINE
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Provided is a recycling process for preparing sertraline, which may be carried out on an industrial scale.
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Page/Page column 10-11
(2008/06/13)
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- Novel processes for preparing sertraline hydrochloride crystalline forms
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The present invention discloses novel and improved processes for preparation of sertraline hydrochloride crystalline form II. Thus, for example, sertraline free base is dissolved in isoamyl alcohol at 25-30° C., pH of the mass is adjusted to 2.0 with conc. hydrochloric acid (36%) at 25-30° C. and then stirred for 14 hours at 25-30° C. Filtered the solid and dried at 65° C. for 4 hours to give sertraline hydrochloride crystalline form II. The present invention also provides a novel process for preparation of sertraline hydrochloride crystalline form I.
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Page/Page column 3-4
(2008/06/13)
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- PROCESS FOR PREPARATION OF SERTRALINE HYDROCHLORIDE FORM I
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Provided is a process for preparation of sertraline HCl Form I on an industrial scale.
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Page/Page column 9-10
(2008/06/13)
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- A HIGHLY STEREOSELECTIVE SYNTHESIS OF SERTRALINE
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The present invention relates to a process for highly stereoselective synthesis of sertraline and sertraline intermediate. Thus, the mixture of 4-(3,4-Dichlorophenyl)-3,4-dihydro-N-methyl-1(2H)-naphthalenimine, 5 % Pd/CaCO3, water and methanol is taken in a hydrogenation flask and then subjected to hydrogenation under a hydrogen pressure of 0.5 Kg at 20 - 35°C for 3 hours 30 minutes. The catalyst is removed by filtration and the solvent is evaporated completely under vacuum to obtain cis-(±)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-naphthalen amine. (trans-(±): 0.2).
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Page/Page column 11-12
(2010/11/25)
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- PROCESSES FOR PREPARING SERTRALINE
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Provided are processes for the preparation of sertraline and sertraline hydrochloride.
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-
Page/Page column 20-21; 24-26
(2008/06/13)
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- CATALYST COMPOSITIONS AND THEIR USE IN THE DE-ENRICHMENT OF ENANTIOMERICALLY ENRICHED SUBSTRATES
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There is provided a process for the de-enrichment of enantiomerically enriched compositions which comprises reacting an enantiomerically enriched composition comprising at least a first enantiomer or diastereomer of a substrate comprising a carbon-heteroatom bond, wherein the carbon is a chiral centre and the heteroatom is a group V heteroatom, in the presence of a catalyst system and optionally a reaction promoter to give a product composition comprising first and second enantiomers or diastereomers of the substrate having a carbon-heteroatom bond, the ratio of second to first enantiomer or disatereomer in the product composition being greater than the ratio of second to first enantiomer or disatereomer in the enantiomerically enriched composition. Preferred catalyst systems include transition metal halide complex of the formula MnXpYr wherein M is a transition metal; X is a halide; Y is a neutral optionally substituted hydrocarbyl complexing group, a neutral optionally substituted perhalogenated hydrocarbyl complexing group, or an optionally substituted cyclopentadienyl complexing group; and n, p and r are integers. The reaction promoter is preferably a halide salt.
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Page/Page column 22-23
(2008/06/13)
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- Asymmetric reduction of substituted indanones and tetralones catalyzed by chiral dendrimer and its application to the synthesis of (+)-sertraline
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A recoverable dendrimeric supported prolinol was used as a catalyst in the asymmetric reduction of indanones and tetralones to give separable cis and trans isomers up to 97% ee. This method was also applied in the enantioselective synthesis of the antidepressant drug (+)-sertraline.
- Wang, Guangyin,Zheng, Changwu,Zhao, Gang
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p. 2074 - 2081
(2007/10/03)
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- PROCESSES FOR THE PREPARATION OF SERTRALINE HYDROCHLORIDE
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The invention relates to processes for the preparation of Schiff's base, and to the use of Schiff's base as intermediate in the preparation of naphthalenamine derivatives which are active compounds for treating the anxiety related disorders. The invention also relates to processes for the preparation of sertraline or a pharmaceutically acceptable salt thereof, and pharmaceutical compositions that include the sertraline.
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Page/Page column 11-12
(2008/06/13)
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- SERTRALINE HYDROCHLORIDE FORM II AND METHODS FOR THE PREPARATION THEREOF
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This invention relates to a method for the preparation of sertraline hydrochloride, (1S-cis)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-1-naphtalenamine hydrochloride, in its crystalline form II.
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Page/Page column 5
(2008/06/13)
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- METHODS FOR PREPARING SERTRALINE HYDROCHLORIDE POLYMORPHS
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This invention relates to crystalline polymorphs of sertraline hydrochloride, i.e. (1S-cis)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-1-naphtalenamine hydrochloride, denominated form (I), (II) and (V) and methods for their preparation.
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Page/Page column 5
(2008/06/13)
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- HYDROGENATION OF IMINE INTERMEDIATES OF SERTRALINE WITH CATALYSTS
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Provided are hydrogenation processes of sertraline imine intermediates with catalysts in various reactors.
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- Sertraline hydrochloride form II and methods for the preparation thereof
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The present invention is directed to Form II of sertraline hydrochloride and novel methods for its preparation. According to the present invention, sertraline hydrochloride Form II may be produced directly form sertraline base or sertraline mandelate. It may also be produced from sertraline hydrochloride solvate and hydrate forms, and crystallized from new solvent systems. Pharmaceutical compositions containing sertraline hydrochloride Form II and methods of treatment using such pharmaceutical compositions are also disclosed.
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- SERTRALINE
-
Crystalline sertraline free base is made by treating a sertraline salt with a base and recovering the sertraline base in crystalline form.
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- Methods for preparation of sertraline hydrochloride polymorphs
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Novel methods for the preparation of sertraline hydrochloride Forms III, V, VI, VII, VII, IX and X are disclosed. According to the present invention, sertraline hydrochloride Form III may be produced by heating sertraline hydrochloride Forms V and VI. Sertraline hydrochloride Forms V and VI may be produced from either sertraline hydrochloride or sertraline base by crystallization. Sertraline hydrochloride Form VII may be produced by suspending sertraline chloride polymorph V in water, followed by filtration. Sertraline hydrochloride Forms VIII and IX may be produced by suspending sertraline base in water followed by acidification and filtration. Sertraline hydrochloride Form X may be produced by suspending sertraline hydrochloride in benzyl alcohol with heating, followed by filtration.
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-
- Salt Selection and Simultaneous Polymorphism Assessment via High-Throughput Crystallization: The Case of Sertraline
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High-throughput (HT) crystallization experiments were conducted with sertraline free base in the presence of mono-, di-and triacidic salt formers. Over 3600 crystallization trials were conducted, leading to the identification and characterization of 18 crystalline salt forms. Due to the large number of crystallization conditions for a given salt type, it was possible to gauge the propensity of a given salt form to exhibit polymorphism. Four salt forms were found to exist (in this limited screen) as monomorphic materials. Unlike the HCl salt in the marketed drug product, the HBr salt appears resistant to polymorphism, crystallizing as a single form from over 140 discrete trials. This observation underscores the lack of predictability of polymorphic behavior of pharmaceuticals even when seemingly minor changes to the composition are made. The experiments highlight the importance of coupling salt selection studies with simultaneous polymorph screening to gain a more comprehensive understanding of solid form diversity as part of the form selection process for pharmaceutical development.
- Remenar, Julius F.,MacPhee, J. Michael,Larson, Bridget K.,Tyagi, Viraj A.,Ho, Jason H.,McIlroy, David A.,Hickey, Magali B.,Shaw, Paul B.,Almarsson, Oern
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p. 990 - 996
(2013/09/05)
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- Efficient kinetic resolution in hydroboration of 1,2-dihydronaphthalenes
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1-Substituted 1,2-dihydronaphthalenes undergo kinetic resolution during asymmetric hydroboration with Rh-QUINAP complexes.
- Maeda, Kenji,Brown, John M.
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p. 310 - 311
(2007/10/03)
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- Metal cataltsts and methods for making and using same
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Compounds having the formula: are disclosed. M1and M2are the same or different and are transition metal atoms or ions; Z2and Z3, independently, are the atoms necessary to complete a 3-12 membered heterocyclic ring; Z1is an alkylene or arylene group; Q1and Q2are the same or different and are electron withdrawing groups; L1and L3, taken together, represent —O—CR13—O—; L2and L4, taken together, represent —O—CR14—O—; and R13and R14are the same or different and are selected from the group consisting of alkyl groups and aryl groups or R13and R14represent alkylene or arylene groups that are directly or indirectly bonded to one another. Methods for making such compounds are also disclosed, as are intermediates which can be used in their preparation. Also disclosed are methods for carrying out C—H insertion reactions using bis-transition metal catalysts, such as the above compounds. Procedures for preparing d-threo methylphenidate, tolterodine, CDP-840, nominfensine, and sertraline, are described.
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- Sertraline hydrochloride Form II and methods for the preparation thereof
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The present invention is directed to Form II of sertraline hydrochloride and novel methods for its preparation. According to the present invention, sertraline hydrochloride Form II may be produced directly form sertraline base or sertraline mandelate. It may also be produced from sertraline hydrochloride solvate and hydrate forms, and crystallized from new solvent systems. Pharmaceutical compositions containing sertraline hydrochloride Form II and methods of treatment using such pharmaceutical compositions are also disclosed.
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-
- Sertraline hydrochloride form II and methods for the preparation thereof
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The present invention is directed to Form II of sertraline hydrochloride and novel methods for its preparation. According to the present invention, sertraline hydrochloride Form II may be produced directly form sertraline base or sertraline mandelate. It may also be produced from sertraline hydrochloride solvate and hydrate forms, and crystallized from new solvent systems. Pharmaceutical compositions containing sertraline hydrochloride Form II and methods of treatment using such pharmaceutical compositions are also disclosed.
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-
- An expedient total synthesis of cis-(+)-sertraline from D-phenylglycine
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An efficient and practical total synthesis of cis-(+)-Sertraline is developed involving intramolecular Friedel-Crafts cyclization of an appropriately tailored D-phenylglycine. (C) 2000 Elsevier Science Ltd.
- Chandrasekhar,Venkat Reddy
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p. 1111 - 1114
(2007/10/03)
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- Efficient kinetic resolution in the asymmetric hydrosilylation of imines of 3-substituted indanones and 4-substituted tetralones
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Kinetic resolution of the N-methyl imines of 3-substituted indanones and 4-substituted tetralones could be accomplished by hydrosilylation with a chiral titanocene catalyst. N-Methyl imines of 4-substituted tetralones were resolved to yield, after hydrolysis of the unreacted starting materials, ketones with high ee's and the amine products with high diastereomeric and enantiomeric purity. The utility of this process was demonstrated in the synthesis of sertraline.
- Yun, Jaesook,Buchwald, Stephen L.
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p. 767 - 774
(2007/10/03)
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- Selective functionalization of 1,2-dihydronaphthalenols leads to a concise, stereoselective synthesis of sertraline
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Asymmetric reductive ring opening of oxabenzonorbornadiene provides dihydronaphthalenols in high ee and good yield. Functionality present in this system can be used to elaborate the core towards a number of targets. As an illustration, a concise stereoselective synthesis of the important antidepressant sertraline is described.
- Lautens, Mark,Rovis, Tomislav
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p. 8967 - 8976
(2007/10/03)
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- Efficient enantioselective synthesis of sertraline, a potent antidepressant, via a novel intramolecular nucleophilic addition to imine
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(equation presented) An efficient enantioselective synthesis of sertraline, an antidepressant, utilizing anionic imine ring closure is described.
- Chen, Cheng-Yi,Reamer, Robert A.
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p. 293 - 294
(2008/02/12)
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- Nontricyclic Antidepressant Agents Derived from cis- and trans-1-Amino-4-aryltetralins
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The need for drugs that lack the obtrusive and limiting side effects of the tricyclic antidepressants has prompted the search for agents with greatly enhanced selectivity for specific mechanisms believed to be essential for antidepressant efficacy.The potential role of derangements of 5-HT pathways in the etiology of depression has long been suspected and has given impetus to the development of newer compounds that accentuate inhibition of serotonin reuptake.This paper presents structure-activity relationship for a series of cis-1-amino-4-(substituted-aryl)tetralins, which are surprisingly potent and selective inhibitors of serotonin uptake in in vitro models.These compounds are pharmacologically distinct from corresponding members of the trans series, which also potently block uptake of dopamine and norepinephrine.The activity in both cis and trans series is stereospecific, being restricted to the cis-(1S,4S) and the trans-(1R,4S) enantiomers.
- Welch, Willard M.,Kraska, Allen R.,Sarges, Reinhard,Koe, B. Kenneth
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p. 1508 - 1515
(2007/10/02)
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