- Catalyst-free and selective synthesis of 2-aminothiophenes and 2-amino-4,5-dihydrothiophenes from 4-thiazolidinones in water
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2-Aminothiophenes and 2-amino-4,5-dihydrothiophenes were selectively and conveniently synthesized from 4-thiazolidinone derivatives. The meaningful product 10m was efficiently synthesized, which is a commonly-used intermediate for preparing olanzapine. The present method holds many advantages, such as easy operation, high yields, is catalyst-free and uses water as the solvent.
- Zeng, Fanxun,Liu, Pengjian,Shao, Xusheng,Li, Zhong,Xu, Xiaoyong
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Read Online
- Design and Performance Validation of a Conductively Heated Sealed-Vessel Reactor for Organic Synthesis
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A newly designed robust and safe laboratory scale reactor for syntheses under sealed-vessel conditions at 250 °C maximum temperature and 20 bar maximum pressure is presented. The reactor employs conductive heating of a sealed glass vessel via a stainless steel heating jacket and implements both online temperature and pressure monitoring in addition to magnetic stirring. Reactions are performed in 10 mL borosilicate vials that are sealed with a silicone cap and Teflon septum and allow syntheses to be performed on a 2-6 mL scale. This conductively heated reactor is compared to a standard single-mode sealed-vessel microwave instrument with respect to heating and cooling performance, stirring efficiency, and temperature and pressure control. Importantly, comparison of the reaction outcome for a number of different synthetic transformations performed side by side in the new device and a standard microwave reactor suggest that results obtained using microwave conditions can be readily mimicked in the operationally much simpler and smaller conventionally heated device.
- Obermayer, David,Znidar, Desiree,Glotz, Gabriel,Stadler, Alexander,Dallinger, Doris,Oliver Kappe
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p. 11788 - 11801
(2016/12/09)
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- Antibodies to Olanzapine Haptens and Use Thereof
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Disclosed is an antibody which binds to olanzapine, which can be used to detect olanzapine in a sample such as in a competitive immunoassay method. The antibody can be used in a lateral flow assay device for point-of-care detection of olanzapine, including multiplex detection of aripiprazole, olanzapine, quetiapine, and risperidone in a single lateral flow assay device.
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Page/Page column
(2014/03/24)
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- ANTIBODIES TO OLANZAPINE HAPTENS AND USE THEREOF
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Disclosed is an antibody which binds to olanzapine, which can be used to detect olanzapine in a sample such as in a competitive immunoassay method. The antibody can be used in a lateral flow assay device for point-of-care detection of olanzapine, including multiplex detection of aripiprazole, olanzapine, quetiapine, and risperidone in a single lateral flow assay device.
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Paragraph 00189; 00190
(2014/03/25)
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- HAPTENS OF OLANZIPINE
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The invention relates to compounds of Formula I, wherein R1, R2, and R3 are defined in the specification, useful for the synthesis of novel conjugates and immunogens derived from olanzapine. The invention also relates to conjugates of an olanzapine hapten and a protein.
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Page/Page column 57
(2014/03/25)
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- Heating under high-frequency inductive conditions: Application to the continuous synthesis of the neurolepticum olanzapine (Zyprexa)
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Hot chemistry! High-frequency inductive heating and flow chemistry are an ideal match for high-temperature synthesis. This is demonstrated in the multistep flow synthesis of the neurolepticum olanzapine (Zyprexa) that included three reactions with inductive heating and two purification steps conducted as continuous processes. Copyright
- Hartwig, Jan,Ceylan, Sascha,Kupracz, Lukas,Coutable, Ludovic,Kirschning, Andreas
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supporting information
p. 9813 - 9817
(2013/09/23)
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- [11C]Olanzapine, radiosynthesis and lipophilicity of a new potential PET 5-HT2 and D2 receptor radioligand
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Olanzapine and its precursor desmethyl-Olanzapine were synthesized from malononitrile, propionaldehyde, 1-fluoro-2-nitrobenzene, and substituted piperazine in 4, 4, 5, and 5 steps with 35%, 32%, 26%, and 32% overall chemical yield, respectively. [11C]Olanzapine was prepared from desmethyl-Olanzapine with [11C]CH3OTf through N-[ 11C]methylation and isolated by HPLC combined with solid-phase extraction (SPE) in 40-50% radiochemical yield based on [11C]CO 2 and decay corrected to end of bombardment (EOB), with 370-740 GBq/μmol specific activity at EOB. The calculated Log P (C Log P) value of [11C]Olanzapine is 3.39.
- Gao, Mingzhang,Shi, Zenas,Wang, Min,Zheng, Qi-Huang
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p. 1953 - 1956
(2013/04/23)
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- THIENOBENZODIAZEPINE MODULATORS OF D1 RECEPTOR, D2 RECEPTOR, AND/OR 5-HT2 RECEPTOR
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The present invention relates to new thienobenzodiazepine modulators of D1 receptors, D2 receptors, and/or 5-HT2 receptors, pharmaceutical compositions thereof, and methods of use thereof.
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Page/Page column 14
(2010/11/03)
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- Bifunctional solid catalysts for chemoselective hydrogenation-cyclisation- amination cascade reactions of relevance for the synthesis of pharmaceuticals
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The benzodiazepines olanzapine and clozapine are nowadays manufactured by a three-step process with a final yield below 50%. An approach to environmentally-friendly intensive processes consists in the development of multifunctional solid catalyst able to catalyze multistep reactions. Here, a bifunctional metal-acid solid catalyst has been prepared and is able to carry out hydrogenation-cyclisation-amination reactions in a cascade process. The catalytic system is illustrated for the synthesis of these important antipsychotics, being an alternative for the current industrial process that requires three steps batch reactions, using mineral acids and bases, and stoichiometric amounts of SnCl2.
- Leyva-Pérez, Antonio,Cabrero-Antonino, Jose R.,Corma, Avelino
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supporting information; experimental part
p. 8203 - 8209
(2010/11/05)
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- Process For Producing Pure And Stable Form Of 2-Methyl-4-(4-Methyl-1-Piperazinyl) -10H-Thieno[2,3-B] [1,5] Benzodiazepine
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Disclosed is an improved process for producing pure and thermally color stable crystalline Form I of 2-methyl-4-(4-methyl-1-piperazinyl)-10H-thieno[2,3-b][1,5]benzodiazepine and product thereof. The process comprises of reacting 2-(2-aminoanilino)-5-methylthiophene-3-carbonitrile with N-methyl piperazine in conjunction with N-methylpiperazine acid salt, to produce 2-methyl-4-(4-methyl-1-piperazinyl)-10H-thieno[2,3-b][1,5]benzodiazepine. Also disclosed is a process for obtaining the Polymorphic Form I of 2-methyl-4-(4-methyl-1-piperazinyl)-10H-thieno[2,3-b][l,5J benzodiazepine by crystallizing the crude 2-methyl-4-(4-methyl-1-piperazinyl)-10H-thieno[2,3-b][1,5]benzodiazepine in a mixture of solvents. Further the invention also provides a new polymorph of Olanzapine, dihydrate Form Ji and process for its preparation and a new hydrate Form J2 of Olanzapine having moisture content 1-3% and process for its preparation.
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Page/Page column 4
(2010/12/29)
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- Process for Producing Pure Form of 2-Methyl-4-(4-Methyl-1-Piperazinyl)-10H-Thieno[2,3-b] [1,5]Benzodiazepine
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Disclosed is a process for producing pure form of 2-methyl-4-(4-methyl-1-piperazinyl)-10H-thieno[2,3-b][1,5] benzodiazepine. The process comprises of reacting 2-(2-aminoanilino)-5-methylthiophene-3-carbonitrile with N-methyl piperazine in conjunction with N-methylpiperazine acid salt, to produce 2-methyl-4-(4-methyl-1-piperazinyl)-10H-thieno[2,3-b][1,5] benzodiazepine. Also disclosed is a process for obtaining the Polymorphic Form I of 2-methyl-4-(4-methyl-1-piperazinyl)-10H-thieno[2,3-b][1,5] benzodiazepine by crystallizing the crude 2-methyl-4-(4-methyl-1-piperazinyl)-10H-thieno[2,3-b][1,5] benzodiazepine in a mixture of solvents.
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Page/Page column 5
(2009/01/24)
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- NOVEL PSYCHOTROPIC AGENTS HAVING GLUTAMATE NMDA ACTIVITY
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The invention provides novel compounds and pharmaceutical compositions for the treatment of psychological and/or psychiatric diseases or disorders.
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Page/Page column 33
(2008/12/05)
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- A PROCESS FOR PRODUCING PURE FORM OF 2-METHYL-4-(4-METHYL-1-PIPERAZINYL)-10H-THIENO[2,3-b][1,5]BENZODIAZEPINE
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Disclosed is a process for producing pure form of 2-methyl-4-(4-methyl-1-piperazinyl)-10H--thieno[2,3-b][1,5] benzodiazepine. The process comprises of reacting 2-(2-aminoanilino)-5--methylthiophene-3-carbonitrile with N-methyl piperazine in conjunction with N-methylpiperazine acid salt, to produce 2-methyl-4-(4-methyl-1-piperazinyl)-10H-thieno[2,3-b][1,5] benzodiazepine. Also disclosed is a process for obtaining the Polymorphic Form I of 2-methyl-4-(4-methyl-1-piperazinyl)-10H-thieno[2,3-b][1,5] benzodiazepine by crystallizing the crude 2-methyl-4-(4-methyl-1-piperazinyl)-10H-thieno[2,3-b][1,5] benzodiazepine in a mixture of solvents.
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Page/Page column 10
(2008/06/13)
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- A PROCESS FOR THE PREPARATION OF ANHYDROUS OLANZOPINE HYDROCHLORIDE OF FORM-1
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Malononitrile is reacted with Propionaldehyde in presence of Sulphur Powder and Triethylamine in N,N-dimethlyformamide to give 5-Amino-4-Cyano-2-Methyl Thiophene. 2-fluoronitrobenzene is condensed with 5-Amino-4-Cyano-2-Methyl Thiophene in Isopropyl alcohol and Potassium Hydroxide powder give 4-cyano-2-methyl-1-(2-nitrophenyl amino) Thiophene. Reduction of 4-cyano-2-methyl-1-(2-nitrophenyl amino) Thiophene with Stannous Chloride and Hydrochloric acid in Isopropyl Alcohol and followed by cyclization to get 4-Amino-2-Methyl-10H-Thieno [2,3,-b][1,5] Benzodiazepine . Condensation of 4-amino-2-methyl-10H-Thieno [2,3,-b][1,5] Benzodiazepine and N-methyl Piperazine in presence of Dimethyl Sulfoxide and Toluene gives Olanzapine Technical grade. In anhydrous form. Recrystallization of the Technical grade anhydrous Olanzapine in Dichloromethane gives anhydrous Olanzapine hydrochloride of Form-I.
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Page/Page column 7-8
(2008/06/13)
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- A synthesis of tritium-labeled olanzapine
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A synthesis of olanzapine, 2-methyl-10-(4-methyl-1-piperazinyl)-4H- thieno[2,3-b][1,5]benzodiazepine, was carried out and the conditions for its tritium labeling were optimized to obtain a tritium-labeled olanzapine preparation with a specific radioactivity of 12 Ci/mmol.
- Shevchenko,Nagaev,Kuznetsov,Polunin,Zozulya,Myasoedov
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p. 378 - 382
(2008/02/03)
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- 2-METHYL-THIENO-BENZODIAZEPINE PROCESS
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The present invention relates to a novel multistep process for preparing thieno-benzodiazepine derivatives having the following structure (I).
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- METHODS OF TREATMENT USING A THIENO-BENZODIAZEPINE
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2-Methyl-4-(4-methyl-1-piperazinyl)-10H-thieno-[2,3-b][1, 5] benzodiazepine, or an acid salt thereof, has pharmaceutical properties, and is of particular use in the treatment of disorders of the central nervous system. The compound has the following structure: STR1
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- Psychoactive substance disorders
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2-Methyl-4-(4-methyl-1-piperazinyl)-10H-thieno-?2,3-b!?1,5!benzodiazepine, or an acid salt thereof, has pharmaceutical properties, and is of particular use in the treatment of disorders relating to the use of psychoactive substances. The compound has the following structure: STR1
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- MENTAL DISORDERS
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2-Methyl-4-(4-methyl-1-piperazinyl)-10H-thieno-[2,3-b][1, 5] benzodiazepine, or an acid salt thereof, has pharmaceutical properties, and is of particular use in the treatment of mental disorders. The compound has the following structure: STR1
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- The synthesis and biological activity of some known and putative metabolites of the atypical antipsychotic agent olanzapine (LY170053)
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4'-N-desmethyl olanzapine (2), olanzapine 4'-N-oxide (3) and 2-hydroxymethyl olanzapine (5), have been prepared and their pharmacology compared to that of the parent compound olanzapine (1). The 4'-N-quaternary glucuronide (8) has also been prepared.
- Calligaro, David O.,Fairhurst, John,Hotten, Terrence M.,Moore, Nicholas A.,Tupper, David E.
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- 2-methyl-thieno-benzodiazepine
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Olanzapine, or an acid salt thereof, has pharmaceutical properties, and is of particular use in the treatment of disorders of the central nervous system. The compound has the following structure: STR1
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- 2-methyl-thieno-benzodiazepine
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2-Methyl-4-(4-methyl-1-piperazinyl)-10H-thieno-[2,3-b][1,5]benzodiazepine, or an acid salt thereof, has pharmaceutical properties, and is of particular use in the treatment of disorders of the central nervous system. The compound has the following structure: STR1
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- 2-METHYL-THIENO-BENZODIAZEPINE
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2-Methyl-10-(4-methyl-1-piperazinyl)-4H-thieno-[2,3-b][1,5] benzodiazepin e, or an acid salt thereof, has pharmaceutical properties, and is of particular use in the treatment of disorders of the central nervous system. The compound has the following structure: STR1
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