DOCSLIB.ORG

(12) STANDARD PATENT (11) Application No. AU 2015226578 B2 (19) AUSTRALIAN PATENT OFFICE

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
(12) STANDARD PATENT (11) Application No. AU 2015226578 B2 (19) AUSTRALIAN PATENT OFFICE (12) STANDARD PATENT (11) Application No. AU 2015226578 B2 (19) AUSTRALIAN PATENT OFFICE (54) Title Heterocyclic compounds, process for preparation of the same and use thereof (51) International Patent Classification(s) C07D 409/12 (2006.01) A61P 25/18 (2006.01) A61K 31/4709 (2006.01) A61P 25/20 (2006.01) A61K 31/496 (2006.01) A61P 25/22 (2006.01) A61K 31/517 (2006.01) A61P 25/24 (2006.01) A61K 31/519 (2006.01) A61P 25/28 (2006.01) A61K 31/538 (2006.01) C07D 409/14 (2006.01) A61K 31/5415 (2006.01) C07D 413/12 (2006.01) A61K 31/55 (2006.01) C07D 417/12 (2006.01) A61P 25/00 (2006.01) C07D 471/04 (2006.01) A61P 25/04 (2006.01) C07D 495/04 (2006.01) A61P 25/14 (2006.01) C07D 519/00 (2006.01) A61P 25/16 (2006.01) (21) Application No: 2015226578 (22) Date of Filing: 2015.03.09 (87) WIPO No: W015/131856 (30) Priority Data (31) Number (32) Date (33) Country 201410083602.8 2014.03.07 CN 201410853950.9 2014.12.31 CN (43) Publication Date: 2015.09.11 (44) Accepted Journal Date: 2017.11.23 (71) Applicant(s) Suzhou Vigonvita Life Sciences Co., Ltd.;Topharman Shandong Co., Ltd.;Shanghai Institute of Materia Medica, Chinese Academy of Sciences (72) Inventor(s) Jiang, Hualiang;Wang, Zhen;Li, Jianfeng;Zhang, Rongxia;He, Yang;Liu, Yongjian;Bi, Minghao;Liu, Zheng;Tian, Guanghui;Chen, Weiming;Yang, Feipu;Wu, Chunhui;Wang, Yu;Jiang, Xiangrui;Yin, Jingjing;Wang, Guan;Shen, Jingshan (74) Agent / Attorney Phillips Ormonde Fitzpatrick, PO Box 323, Collins Street West, VIC, 8007, AU (56) Related Art US 2010/0063047 Al Grembecka, J. et al, "Menin-MLL inhibitors reverse oncogenic activity of MLL fusion proteins in Leukemia", Nature Chemical Biology, 2012, Vol. 8, No. 3, pp 277-284 WO 2009/094279 Al WO 2013024291 A2 CAS Registry Number 1355745-62-8; STN Entry Date 7 February 2012; 6-ethyl-4 [4-[(5-methyl-1,2,4-oxadiazol-3-yl)methyl]-l-piperazinyl]- Thieno[2,3-d]pyrimidine dimethyl-4-[4-[(3-methyl-5-isoxazolyl)methyl]-1-piperazinyl]- Thieno[2,3 d]pyrimidine CAS Registry Number 1311748-02-3; STN Entry Date 7 July 2011; 4-[3-methyl-4 [(1-methyl-1 H-imidazol-2-yl)methyl]-1 -piperazinyl]- Thieno[2,3-d]pyrimidine CAS Registry Number 1301595-14-1; STN Entry Date 27 May 2011; 2-[[4-(6 ethylthieno[2,3-d]pyrimidin-4-y)-1-piperazinyl]methyl]- 4-Quinazolinamine CAS Registry Number 1269222-01-6; STN Entry Date 21 March 2011; 5-[[4-(5 ethyl-6-methylthieno[2,3-d]pyrimidin-4-y)-1-piperazinyl]methyl]- 2-Furanmethanol CAS Registry Number 930055-49-5; STN Entry Date 13 April 2007; 42 [[4-[2-[(diethylamino)methyl]-5,6-dimethylthieno[2,3-d]pyrimidin-4-yl]-1 piperazinyl]methyl]- (3H)-Quinazolinone CAS Registry Number 1330518-02-9; STN Entry Date 9 September 2011; 5,6 dimethyl-4-[4-(3-thienylmethyl)-1-piperazinyl]- Thieno[2,3-d]pyrimidine CAS Registry Number 434916-97-9; STN Entry Date 28 June 2002; 4-[4-(1,3 benzodioxol-5-ylmethyl)-1-piperazinyl]-2,6-dimethyl- Thieno[2,3-d]pyrimidine CAS Registry Number 1294647-95-2; STN Entry Date 15 May 2011; 6-ethyl-4-[4-[2 (2-thienyl)ethyl]-1-piperazinyl]- Thieno[2,3-d]pyrimidine CAS Registry Number 1323856-54-7; STN Entry Date 26 August 2011; 4-[4-[(2,3 dihydro-1,4-benzodioxin-6-yl)methyl]-1-piperazinyl]- Thieno[2,3-d]pyrimidine CAS Registry Number 920727-99-7; STN Entry Date 13 February 2007; 5,6 dimethyl-2-[(4-thieno[2,3-d]pyrimidin-4-y-1 -piperazinyl)methyl]-Thieno[2,3 d]pyrimidin-4(1 H)-one CAS Registry Number 1331035-38-1; STN Entry Date 11 September 2011; 6,7,8,9 tetrahydro-3-[(4-thieno[2,3-d]pyrimidin-4-yl-1-piperazinyl)methyl]- 5H-1,2,4 Triazolo[4,3-a]azepine (12) I (10) (43)E~# WO 2015/131856 A1 2015 * 9 T] 11 H (11.09.2015) WIPO I PCT (51) 04"*j3k* : (72) tA: an (JIANG, Hualiang); NI *M C07D 409/12 (2006.01) A61K31/5415 (2006.01) SThIfl}+t 555 5, Shanghai 201203 (CN). o C07D 471/04 (2006.01) A61K31/55 (2006.01) E (WANG, Zhen); [: SlK[TIiMtflK 1 % C07D 409/14 (2006.01) A61P 25/00 (2006.01) 555 v, Shanghai 201203 (CN) * !JI*E (LI, Jian C07D 519/00 (2006.01) A61P 25/18 (2006.01) feng); %9 9 555 Shang C07D 495/04 (2006.01) A61P 25/24 (2006.01) hai 201203 (CN)o (ZHANG, Rongxia); A C07D 417/12 (2006.01) A61P 25/22 (2006.01))N, hai Rongxi 201 C07D 413/12 (2006.01) A61P 25/20 (2006.01) i hS i I llI+Z9 S 555 r, Shanghai 201203 A61K31/496 (2006.01) A61P25/28 (2006.01) (CN)o fi# (HE, Yang); +1 l A61K 31/519 (2006.01) A61P 25/04 (2006.01) }+ Z t 555 V , Shanghai 201203 (CN) o 1Ac A61K31/4709 (2006.01) A61P 25/16 (2006.01) (LIU,Yongjian); T NSWJ 2VX1JFf A61K31/517(2006.01) A61P 25/14 (2006.01) RZ A4OLY 49 5, Shandong 262123 (CN)0 o A A61K31/538 (2006.01) M (BI, Minghao); [AdJf $ # Tir9ttm (21) 04$ift : PCT/CN2015/073854 RX (4Li7zJ 49 Shandong 262123 (CN)o tijE (LIU, Zheng); Th iJ M #)ttETVfrtt* (22) F$4*i: 2015 4 3 A 9 H (09.03.2015) a 7A L$J L 49 V, Shandong 262123 (CN) , EE% (25) $ifi . (TIAN, Guanghui); +1 1 M V5A1W' M IT_ R N Ex ItMAAE k x l 398 : D % 10 W, Jiangsu (26) &$*#: T 215123 (CN)o Mi$ (CHEN, Weiming); Ji 49 5, Shan -- (30) 'LtE: #A($$F R4Xa*7L 201410083602.8 2014 4 3 A 7 H (07.03.2014) CN dong262123(CN)o (YANG,Feipu); t'I 201410853950.9 2014 % 12 A 31 H (31.12.2014) CN 4 SIT lli4 t 555 5, Shanghai 201203 (CN)0 o #l (WU, Chunhui); + EI tT$tK (71) $iA: ~ (SHANGHAI MIl]}+i26 555 5, Shanghai 201203 (CN) o1:E* INSTITUTE OF MATERIA MEDICA, CHINESE (WANG, Yu); +' $1I4 9TIll}t 555 , ACADEMY OF SCIENCES) [CN/CN]; +' IL 4t Shanghai 201203 (CN) *MI$A (JIANG, Xiangrui); -S9itfll}+tY 555 ',tShanghai 201203 (CN)o $ + l 555 , Shanghai = RE WE* I*EK 4jk$ (SUZHOU VIGON- 201203 (CN) o Ift (YIN, Jingjing); N1 dJfi SV VITA LIFE SCIENCES CO., LTD.) [CN/CN]; +1 Nl MZX %EX ta(74L0 49 v, Shandong V-V, ) I IR E5N A tEx A,7Y 398 262123 (CN)0 oI: (WANG, Guan); ThPI1tT 5 D%, 10W, Jiangsu 215123 (CN)0 o NA$4ltW* S 9T ll}+t9 555 , Shanghai 201203 (CN)0ot =S' (TOPHARMAN SHANDONG CO., il (SHEN, Jingshan); SI@T $$K9Tll}+ LTD.) [CN/CN]; +1 1 dJ #VX1M MAcR ZYt 555 5, Shanghai 201203 (CN)0 Z 7xJA(LY 49 5, Shandong 262123 (CN)o (54) Title: HETEROCYCLIC COMPOUNDS, AND PREPARATION METHOD AND USE THEREOF ~=(5 4) ~U$:~T ~~tT~4~f N R3 R2 R B D S (57) Abstract: Provided are heterocyclic compounds represented by formula (I), stereoisomers or pharmaceutically acceptable salts O of said compounds, a pharmaceutical composition of said compounds, and an application of said compounds in the preparation of a drug for the prevention and/or treatment of a central nervous system disease. (57) RH Xf hAY ALI k_- n J- Pi:tt4A _CKM qI-"T nAArv R W O 2 0 15/13 18 5 6 A 1|l IIl l||lIll1|||I||I|||||||||||I|||||I|||II |lllll ||I|||||||||||||||||||||I ||||| (74) 1fW 4h* {iW " Rf SMPR 4k (84) M J(TY hI' A 5*V-#-fT$ fl ttf Ex (KINGSOUND & PARTNERS); +1N LTIj tfE)): ARIPO (BW, GH, GM, KE, LR, LS, MW, MZ, 7t4Fi 116 VI B 11 , Beijing NA, RW, SD, SL, ST, SZ, TZ, UG, ZM, ZW), rX3 100097 (CN)o (AM, AZ, BY, KG, KZ, RU, TJ, TM), Wt )II (AL, AT, BE, BG, CH, CY, CZ, DE, DK, EE, ES, Fl, FR, GB, GR, (81) 4Hl! (W h ' , HR, HU, IE, IS, IT, LT, LU, LV, MC, MK, MT, NL, NO, NTtP): AE, AG, AL, AM, AO, AT, AU, AZ, BA, BB, PL, PT, RO, RS, SE, SI, SK, SM, TR), OAPI (BF, BJ, BG, BH, BN, BR, BW, BY, BZ, CA, CH, CL, CN, CO, CF, CG, CI, CM, GA, GN, GQ, GW, KM, ML, MR, NE, CR, CU, CZ, DE, DK, DM, DO, DZ, EC, EE, EG, ES, Fl, SN, TD, TG)O GB, GD, GE, GH, GM, GT, HN, HR, HU, ID, IL, IN, IR, IS, JP, KE, KG, KN, KP, KR, KZ, LA, LC, LK, LR, LS, *2[$$$ : LU, LY, MA, MD, ME, MG, MK, MN, MW, MX, MY' iFArtt9tNm 21 (3))o MZ, NA, NG, NI, NO, NZ, OM, PA, PE, PG, PH, PL, PT, QA, RO, RS, RU, RW, SA, SC, SD, SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW0 DESCRIPTION HETEROCYCLIC COMPOUNDS, PROCESS FOR PREPARATION OF THE SAME AND USE THEREOF TECHNICAL FIELD The present invention belongs to the field of medicinal chemistry. More specifically, the present invention provide a heterocyclic compound represented by general formula (1), stereoisomer or pharmaceutically acceptable salt thereof, the producing processes thereof, pharmaceutical compositions and their use in the manufacture of drugs for the treatment of central nervous system diseases. BACKGROUND ART Mental illness is a group of neurological disease mainly manifested in behavior and mental activity disorder, clinically manifested in abnormal mental activity, specifically manifested in disorders in varying degrees in perception, thinking, attention, memory, emotion, behavior, intelligence and consciousness.
Load more

Recommended publications
  • Aldrich FT-IR Collection Edition I Library
    Aldrich FT-IR Collection Edition I Library Library Listing – 10,505 spectra This library is the original FT-IR spectral collection from Aldrich. It includes a wide variety of pure chemical compounds found in the Aldrich Handbook of Fine Chemicals. The Aldrich Collection of FT-IR Spectra Edition I library contains spectra of 10,505 pure compounds and is a subset of the Aldrich Collection of FT-IR Spectra Edition II library. All spectra were acquired by Sigma-Aldrich Co. and were processed by Thermo Fisher Scientific. Eight smaller Aldrich Material Specific Sub-Libraries are also available. Aldrich FT-IR Collection Edition I Index Compound Name Index Compound Name 3515 ((1R)-(ENDO,ANTI))-(+)-3- 928 (+)-LIMONENE OXIDE, 97%, BROMOCAMPHOR-8- SULFONIC MIXTURE OF CIS AND TRANS ACID, AMMONIUM SALT 209 (+)-LONGIFOLENE, 98+% 1708 ((1R)-ENDO)-(+)-3- 2283 (+)-MURAMIC ACID HYDRATE, BROMOCAMPHOR, 98% 98% 3516 ((1S)-(ENDO,ANTI))-(-)-3- 2966 (+)-N,N'- BROMOCAMPHOR-8- SULFONIC DIALLYLTARTARDIAMIDE, 99+% ACID, AMMONIUM SALT 2976 (+)-N-ACETYLMURAMIC ACID, 644 ((1S)-ENDO)-(-)-BORNEOL, 99% 97% 9587 (+)-11ALPHA-HYDROXY-17ALPHA- 965 (+)-NOE-LACTOL DIMER, 99+% METHYLTESTOSTERONE 5127 (+)-P-BROMOTETRAMISOLE 9590 (+)-11ALPHA- OXALATE, 99% HYDROXYPROGESTERONE, 95% 661 (+)-P-MENTH-1-EN-9-OL, 97%, 9588 (+)-17-METHYLTESTOSTERONE, MIXTURE OF ISOMERS 99% 730 (+)-PERSEITOL 8681 (+)-2'-DEOXYURIDINE, 99+% 7913 (+)-PILOCARPINE 7591 (+)-2,3-O-ISOPROPYLIDENE-2,3- HYDROCHLORIDE, 99% DIHYDROXY- 1,4- 5844 (+)-RUTIN HYDRATE, 95% BIS(DIPHENYLPHOSPHINO)BUT 9571 (+)-STIGMASTANOL
    [Show full text]
  • European Patent Office of Opposition to That Patent, in Accordance with the Implementing Regulations
    (19) TZZ ¥Z_T (11) EP 2 655 308 B1 (12) EUROPEAN PATENT SPECIFICATION (45) Date of publication and mention (51) Int Cl.: of the grant of the patent: C07C 45/45 (2006.01) C07C 49/84 (2006.01) 07.03.2018 Bulletin 2018/10 (86) International application number: (21) Application number: 11804542.6 PCT/EP2011/073172 (22) Date of filing: 19.12.2011 (87) International publication number: WO 2012/084770 (28.06.2012 Gazette 2012/26) (54) PROCESS FOR THE MANUFACTURE OF DIBENZOYLMETHANE DERIVATIVES VERFAHREN ZUR HERSTELLUNG VON DIBENZOYLMETHANDERIVATEN PROCÉDÉ DE PRODUCTION DE DÉRIVÉS DE DIBENZOYLMÉTHANE (84) Designated Contracting States: • NANDURKAR NITIN S ET AL: "Synthesis of AL AT BE BG CH CY CZ DE DK EE ES FI FR GB sterically hindered 1,3-diketones", SYNTHETIC GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO COMMUNICATIONS, TAYLOR & FRANCIS PL PT RO RS SE SI SK SM TR GROUP, PHILADELPHIA, PA, vol. 37, no. 23, 1 January 2007 (2007-01-01), pages 4111-4115, (30) Priority: 20.12.2010 EP 10195971 XP009144707, ISSN: 0039-7911, DOI: DOI:10.1080/00397910701572803 (43) Date of publication of application: • GUOQING ZHANG ET AL: "Polymorphism and 30.10.2013 Bulletin 2013/44 Reversible Mechanochromic Luminescence for Solid-State Difluoroboron Avobenzone", (73) Proprietor: DSM IP Assets B.V. JOURNAL OF THE AMERICAN CHEMICAL 6411 TE Heerlen (NL) SOCIETY, AMERICAN CHEMICAL SOCIETY, US, vol. 132, 1 January 2010 (2010-01-01), pages (72) Inventor: WEHRLI, Christof 2160-2162, XP007917212, ISSN: 0002-7863, DOI: CH-4002 Basel (CH) DOI:10.1021/JA9097719 [retrieved on 2010-01-28] • FRANEK W: "New Dithio-bis-(diaroylmethanes) (74) Representative: Berg, Katja et al and Acetyl Diaroylchloromethyl Disulfides: DSM Nutritional Products AG Attractive Synthons and Precursors for the Wurmisweg 576 Liberation of Highly Reactive Dithiiranes or CH-4303 Kaiseraugst (CH) Thiosulfines", MONATSHEFTE FUR CHEMIE, SPRINGER VERLAG WIEN, AT, vol.
    [Show full text]
  • Hydrogen/Formic Acid Production from Natural Gas with Zero Carbon Dioxide Emissions MARK
    Journal of Natural Gas Science and Engineering 49 (2018) 84–93 Contents lists available at ScienceDirect Journal of Natural Gas Science and Engineering journal homepage: www.elsevier.com/locate/jngse Hydrogen/formic acid production from natural gas with zero carbon dioxide emissions MARK ∗ Jorge A. Pena Lopez, Ibubeleye Somiari, Vasilios I. Manousiouthakis Department of Chemical and Biomolecular Engineering, University of California, Los Angeles (UCLA), 5531 Boelter Hall, Los Angeles, CA 90095-1592, USA ARTICLE INFO ABSTRACT Keywords: Presented in this work is a novel process flowsheet that co-produces hydrogen and formic acid from natural gas, Formic acid without emitting any carbon dioxide. This is achieved by employing a reaction cluster that involves commer- Hydrogen cially available technologies, such as combustion, dry reforming, water-gas shift reaction, pressure-swing ad- Natural gas sorption, and formic acid production via methyl formate hydrolysis. Thermodynamic and energetic self-suffi- Energetic self-sufficiency ciency analysis imposes operating limits on the proposed process, within which a feasible flowsheet is developed. Reaction cluster Heat and power integration analysis reveals that heat engine and heat pump subnetworks are sufficient to meet Heat and power integration the flowsheet's energy requirements without violating energetic self-sufficiency constraints. Operating cost analysis reveals a revenue to cost ratio of 8.8, when the system's operating point is chosen to maximize hydrogen production. 1. Introduction and thus its use would completely address air quality issues in cities. Finally, hydrogen's production from renewable energy would not lead The use of oil derived gasoline as fuel for light vehicle based to carbon dioxide emissions to the atmosphere.
    [Show full text]
  • Durham E-Theses
    Durham E-Theses Functionalised Pyridyl- and Pyrimidyl- Boronic acids and derived new Biheteroaryls Smith, Amy Elizabeth How to cite: Smith, Amy Elizabeth (2005) Functionalised Pyridyl- and Pyrimidyl- Boronic acids and derived new Biheteroaryls, Durham theses, Durham University. Available at Durham E-Theses Online: http://etheses.dur.ac.uk/2751/ Use policy The full-text may be used and/or reproduced, and given to third parties in any format or medium, without prior permission or charge, for personal research or study, educational, or not-for-prot purposes provided that: • a full bibliographic reference is made to the original source • a link is made to the metadata record in Durham E-Theses • the full-text is not changed in any way The full-text must not be sold in any format or medium without the formal permission of the copyright holders. Please consult the full Durham E-Theses policy for further details. Academic Support Oce, Durham University, University Oce, Old Elvet, Durham DH1 3HP e-mail: [email protected] Tel: +44 0191 334 6107 http://etheses.dur.ac.uk 2 University of Durham A Thesis Entitled Functionalised Pyridyl- and Pyrimidyl- Boronic Acids and Derived New Biheteroaryls Submitted by Amy Elizabeth Smith, B.Sc. (Hons) (Ustinov College) Department of Chemistry A Candidate for the Degree of Doctor of Philosophy 2005 The copyright of this thesis rests wnh the author or the university to which к was submitted. No quotation from It, or Information derived from It may be published wHhout the prior written consent of the author or university, and any Information derived from ท should be acknowledged.
    [Show full text]
  • 200225128.Pdf
    Members of the Examination Committee: Prof. Dr. ir. Nico Boon (Chairman) Department of Biotechnology, Faculty of Bioscience Engineering, Ghent University Prof. Dr. Adrian Dobbs Department of Pharmaceutical, Chemical and Environmental Sciences, Faculty of Engineering and Science, University of Greenwich Dr. Steven De Jonghe Laboratory of Virology and Chemotherapy, Rega Institute for Medical Research, KU Leuven Prof. Dr. Serge Van Calenbergh Laboratory of Medicinal Chemistry, Faculty of Pharmaceutical Sciences, Ghent University Prof. Dr. ir. Matthias D’hooghe Department of Green Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University Prof. Dr. ir. Marjan De Mey Department of Biotechnology, Faculty of Bioscience Engineering, Ghent University This work was supported by the Agency for Innovation by Science and Technology, Flanders (IWT- SBO project 100014) and the Special Research Fund (BOF project BOF14/DC1/032) Promotor: Prof. Dr. ir. Christian Stevens Department of Green Chemistry and Technology Faculty of Bioscience Engineering Ghent University Dean: Prof. Dr. ir. Marc Van Meirvenne Rector: Prof. Dr. ir. Rik Van de Walle Faculty of Bioscience Engineering 2019 ir. Laurens De Coen Synthesis and Preliminary Biological Evaluation of Furo- and Oxazolopyrimidine Analogues Thesis submitted in fulfilment of the requirements for the degree of Doctor (PhD) in Applied Biological Sciences: Chemistry and Bioprocess Technology Dutch translation of the title: Synthese en preliminaire biologische evaluatie van furo- en oxazolopyrimidines Please cite as: De Coen, L.; ‘Synthesis and Preliminary Biological Evaluation of Furo- and Oxazolopyrimidine Analogues’, PhD Dissertation, Ghent University, 2019 Cover illustration: Exploring Chemical Space (Laurens De Coen) ISBN number: 9789463572064 The author and the promotor give authorization to consult and copy parts of this work for personal use only.
    [Show full text]
  • Applications of Boronic Acids in Organic Synthesis
    Applications of Boronic Acids in Organic Synthesis A dissertation presented by Pavel Starkov in partial fulfilment of the requirements for the award of the degree of DOCTOR OF PHILOSOPHY at UNIVERSITY COLLEGE LONDON Department of Chemistry Christopher Ingold Laboratories University College London 20 Gordon Street WC1H 0AJ London Declaration This dissertation is the result of my own work. Where information has been derived from other sources it has been clearly indicated so and acknowledged accordingly. /Pavel Starkov/ ii Abstract This thesis describes progress on the application of boronic acids and borate esters as catalysts and reagents in synthetic organic synthesis, focusing on two areas: one-pot enolate formation/aldol reactions and amide bond formation. Chapter 1 introduces the reader to boronic acids and derivatives thereof, their methods of preparation and their use in synthetic organic chemistry as reactants, reagents and catalysts. Chapter 2 covers current chemical methods and cellular alternatives for amide bond formation. Here, we also discuss our use of boron reagents for the activation of carboxylic acids as well as amides. Chapter 3 introduces a new concept in catalytic aldol reactions, i.e. an alternative strategy to access boron enolates in situ. The work covers successful demonstration of the feasibility of such an approach on an intramolecular system. A novel variation of aerobic Chan–Evans– Lam coupling, an intramolecular coupling of an aliphatic alcohol with a boronic acid using catalytic copper, is also introduced Chapter 4 builds on our observations on gold catalysis and especially that in relation to electrophilic halogenations. Chapter 5 contains full details of the experimental procedures.
    [Show full text]
  • Chemical Engineering Transactions
    1705 A publication of CHEMICAL ENGINEERING TRANSACTIONS The Italian Association VOL. 39, 2014 of Chemical Engineering www.aidic.it/cet Guest Editors: Petar Sabev Varbanov, Jiří Jaromír Klemeš, Peng Yen Liew, Jun Yow Yong Copyright © 2014, AIDIC Servizi S.r.l., ISBN 978-88-95608-30-3; ISSN 2283-9216 DOI: 10.3303/CET1439285 Simulation of Reactive Distillation Column for Biodiesel Production at Optimum Conditions Süleyman Karacan*a, Filiz Karacanb aAnkara University, Engineering Faculty, Department of Chemical Engineering, Tandoğan 06100, Ankara, Turkey. bTurkish Atomic Energy Authority, Sarayköy Nuclear Research and Training Centre, Istanbul Road 30 km., 06983 Saray, Ankara, Turkey. [email protected] Biodiesel is defined as a mixture of fatty acid alkyl esters which are commonly produced from triglycerides and alcohol through transesterification reaction in the presence of alkali catalysts. In this work canola oil and methanol were used in this research as the feedstocks, and potassium hydroxide, potassium methoxide, were used as different formulations of catalysts. A laboratory-scale continuous-flow Reactive Distillation column system was simulated at optimum conditions by Aspen HYSYS. The homogeneous alkali and acid catalyzed was applied to the system. The non-catalytic reaction, where the absence of catalyst simplifies the purification procedures and the products can be easily separated. The critical operating conditions and high consumption of methanol and energy make it uneconomical. Based on the optimization of energy integration and methanol recovery strategies, optimization strategies were assessed for saving energy and recovery methanol. 1. Introduction Biodiesel is a clean burning fuel derived from a renewable feedstock such as vegetable oil or animal fat.
    [Show full text]
  • WO 2008/122988 Al
    (12) INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property Organization International Bureau (10) International Publication Number (43) International Publication Date PCT 16 October 2008 (16.10.2008) WO 2008/122988 Al (51) International Patent Classification: (74) Agents: SUBRAMANIAM, Hariharan et al; SUBRA- C07C 46/10 (2006.01) C07C 50/32 (2006.01) MANIAM, NATARAJ & ASSOCIATES, Patent & Trade mark Attorneys, E 556, Greater Kailash-II, New Dehli 110 (21) International Application Number: 048 (IN). PCT/IN2008/000216 (81) Designated States (unless otherwise indicated, for every (22) International Filing Date: 3 April 2008 (03.04.2008) kind of national protection available): AE, AG, AL, AM, AO, AT,AU, AZ, BA, BB, BG, BH, BR, BW, BY, BZ, CA, (25) Filing Language: English CH, CN, CO, CR, CU, CZ, DE, DK, DM, DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, HN, HR, HU, ID, (26) Publication Language: English IL, IN, IS, JP, KE, KG, KM, KN, KP, KR, KZ, LA, LC, LK, LR, LS, LT, LU, LY, MA, MD, ME, MG, MK, MN, (30) Priority Data: MW, MX, MY, MZ, NA, NG, NI, NO, NZ, OM, PG, PH, 686/MUM/2007 5 April 2007 (05.04.2007) IN PL, PT, RO, RS, RU, SC, SD, SE, SG, SK, SL, SM, SV, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, (71) Applicant and ZA, ZM, ZW (72) Inventor: CADILA HEALTHCARE LIMITED (84) Designated States (unless otherwise indicated, for every [IN/IN]; Zydus Tower, Satellite Cross Roads, Amedad- kind of regional protection available): ARIPO (BW, GH, abad 380 015, Gujara (IN).
    [Show full text]
  • Process for the Preparation of Statins in the Presence of Base
    (19) TZZ ¥_T (11) EP 2 665 723 B1 (12) EUROPEAN PATENT SPECIFICATION (45) Date of publication and mention (51) Int Cl.: of the grant of the patent: C07D 405/06 (2006.01) C07D 413/12 (2006.01) 22.07.2015 Bulletin 2015/30 C07D 419/12 (2006.01) (21) Application number: 12701325.8 (86) International application number: PCT/EP2012/050470 (22) Date of filing: 13.01.2012 (87) International publication number: WO 2012/098049 (26.07.2012 Gazette 2012/30) (54) PROCESS FOR THE PREPARATION OF STATINS IN THE PRESENCE OF BASE VERFAHREN ZUR HERSTELLUNG VON STATINEN UNTER VERWENDUNG EINER BASE PROCÉDÉ DE PRÉPARATION DE STATINES EN PRÉSENCE D’UNE BASE (84) Designated Contracting States: • LANGE, DE, Ben AL AT BE BG CH CY CZ DE DK EE ES FI FR GB NL-6100 AA Echt (NL) GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR (74) Representative: De Vroom, Erik DSM Intellectual Property (30) Priority: 18.01.2011 EP 11151280 P.O. Box 4 11.10.2011 EP 11184685 6100 AA Echt (NL) (43) Date of publication of application: (56) References cited: 27.11.2013 Bulletin 2013/48 WO-A1-2005/042522 WO-A2-01/96311 WO-A2-02/098854 WO-A2-2010/077062 (73) Proprietor: DSM Sinochem Pharmaceuticals WO-A2-2010/140765 Netherlands B.V. 2613 AX Delft (NL) • BAN-CHI CHEN ET AL: "Synthesis of d3- cerivastatin for use as internal standard in a (72) Inventors: LC/MS/MS method developed for quantitation of • BESSEMBINDER, Karin, Henderika, Maria the drug in human serum", JOURNAL OF NL-6100 AA Echt (NL) LABELLED COMPOUNDS AND • HEEMSKERK, Dennis RADIOPHARMACEUTICALS, vol.
    [Show full text]
  • Monitoring a Claisen-Schmidt Condensation Reaction by NMR in the Teaching Class
    Monitoring a Claisen-Schmidt Condensation Reaction by NMR in the teaching Class Scheme 1. Claisen-Schmidt condensation reaction for the synthesis of dibenzalacetone analog The development of high-performance benchtop NMR spectrometers provides a practical and information-rich way to monitor on-line/in-line the progress of chemical reaction. NMR provides not only the structural information about the different chemical species involved in the reaction but also quantitative information about the concentration of reactants and products. By following the conversion in real time, chemists get the required insight to understand the kinetics of the reaction. Another advantage of using NMR for reaction monitoring is the ability to observe reaction intermediates. These can often be missed with endpoint reaction analysis, since intermediate, by definition, gets produced in the early stage and consumed during later stage of the reaction. In recent years, the availability and affordability of benchtop NMR systems have offered the opportunity for schools to incorporate NMR spectroscopic techniques into organic chemistry curricula. With simple button-clicking, instructors and students can perform different NMR experiments to confirm the reaction products, or to monitor a reaction with NMR. This application note describes an example of using the Spinsolve 60 MHz Carbon ULTRA to monitor a frequently used reaction in the organic chemistry laboratory – the Claisen-Schmidt (or cross-aldol, Scheme 1) condensation reaction to synthesize dibenzalacetone. Students can visualize the kinetic profile of different chemical components in real-time. They can also observe the reaction intermediate, which is a concept that is seldomly demonstrated in laboratory experiment since intermediate species are not easily isolated from the reaction mixture for characterization.
    [Show full text]
  • The Development and Use of Chiral 4-Dimethylaminopyridine-N-Oxide As an Organocatalyst
    THE DEVOLOPMENT AND USE OF CHIRAL 4- DIMETHYLAMINOPYRIDINE-N-OXIDE AS AN ORGANOCATALYST A Dissertation Submitted to the Graduate Faculty of the North Dakota State University of Agriculture and Applied Science By Jesse Jo Joyce In Partial Fulfillment of the Requirements for the Degree of MASTER OF SCIENCE Major Department: Chemistry and Biochemistry July 2018 Fargo, North Dakota North Dakota State University Graduate School Title The Development and Use of Chiral 4-Dimethylaminopyridine-N-Oxide as an Organocatalyst By Jesse Jo Joyce The Supervisory Committee certifies that this disquisition complies with North Dakota State University’s regulations and meets the accepted standards for the degree of MASTER OF SCIENCE SUPERVISORY COMMITTEE: Mukund Sibi, PhD Chair Gregory Cook, PhD Seth Rasmussen, PhD Yongki Choi, PhD Approved: 11/09/18 Gregory Cook, PhD Date Department Chair ABSTRACT Organocatalysis is a field that has bloomed over the last decades. With the field’s promise of being able to mimic nature and afford products in a synergistic manner to traditional Lewis acid catalysis, several interesting discoveries have been made. Owing to the vastness of the field as it exists today, this document will focus on two main aspects; cinchona alkaloid (and derivatives) as used in common carbon-carbon bond forming reactions and kinetic resolution via 4-dimethyl aminopyridine-N-oxide derivative driven acylation. Kinetic resolution via organocatalysis has the potential to react one enantiomer of a racemic mixture without affecting the other. The highlight of this screening was an s factor of 9 which was produced using optimized conditions using a catalyst designated DMAPO-IV.
    [Show full text]
  • Catalysts for Organic Chemistry Brochure
    CONTENTS COUPLING REACTIONS WITH CATALYSTS AND REAGENTS FROM ACROS ORGANICS ...........................................................3 HECK-REACTION (I) ...........................................................................................................................................................5 SONOGASHIRA-REACTION (II) ............................................................................................................................................6 SUZUKI-REACTION (III) .......................................................................................................................................................7 STILLE-REACTION (IV) .......................................................................................................................................................8 HIYAMA-COUPLING (V) ......................................................................................................................................................9 KUMADA-COUPLING (VI) ..................................................................................................................................................10 BUCHWALD-HARTWIG-REACTION (VII) .............................................................................................................................11 TSUJI-TROST-REACTION (VIII) ..........................................................................................................................................12 CYANATION OF AROMATIC HALIDES (IX) ...........................................................................................................................13
    [Show full text]