DOCSLIB.ORG

Pyrimidine Derived Schiff Bases at Conventional and Microwave Heating Conditions

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
Pyrimidine Derived Schiff Bases at Conventional and Microwave Heating Conditions Araştırma Makalesi BAUN Fen Bil. Enst. Dergisi, 22(2), 428-438, (2020) DOI:10.25092/baunfbed.707673 J. BAUN Inst. Sci. Technol., 22(2), 428-438, (2020) Preparation of novel imidazo[1,2-a]pyrimidine derived schiff bases at conventional and microwave heating conditions Tuğba GÜNGÖR* Çanakkale Onsekiz Mart University, Faculty of Sciences and Arts, Department of Chemistry, Natural Products and Drug Research Laboratory, Terzioğlu Campus, Çanakkale. Geliş Tarihi (Received Date): 11.10.2019 Kabul Tarihi (Accepted Date): 30.01.2020 Abstract In this study, novel imidazo[1,2-a]pyrimidine derived schiff bases were synthesized via imine formation reaction and characterized with various spectral analysis such as FT- IR, 1H NMR, 13C NMR and MS. In addition to conventional heating reactions, microwave-assisted synthesis was applied to the C=N bond formation step. The reactions were carried out at reflux temperature in toluene and magnesium sulfate as drying agent. While final products were obtained at 10-36 h reaction times with moderate to good yields at conventional heating conditions, synthesized at 45-120 min reaction times with good yields at microwave heating conditions. Results showed that microwave-assisted synthesis which is a well-known green process for the synthesizing organic molecules provides to obtain shorter reaction times and higher yields in our study. Keywords: Schiff base, imidazo[1,2-a]pyrimidine, microwave synthesis, conventional heating. Geleneksel ve mikrodalga ısıtma koşullarında yeni imidazo[1,2-a]pirimidin türevi schiff bazlarının hazırlanması Öz Bu çalışmada yeni imidazo[1,2-a]pirimidin türevli schiff bazları, imin oluşum reaksiyonu ile sentezlenmiş ve FT-IR, 1H NMR, 13C NMR, MS gibi çeşitli spektral analizler ile yapıları aydınlatılmıştır. Geleneksel ısıtma ile gerçekleştirilen reaksiyonlara ek olarak C=N oluşum basamağına mikrodalga-destekli sentez de uygulanmıştır. Reaksiyonlar, magnezyum sülfatın kurutucu olarak kullanıldığı, toluen * Tuğba GÜNGÖR, [email protected], https://orcid.org/0000-0001-5261-1856 428 GÜNGÖR T. içerisinde kaynama sıcaklığı koşullarında yürütülmüştür. Son ürünler, geleneksel ısıtma koşullarında 10-36 sa reaksiyon sürelerinde orta-iyi verimlerle elde edilirken, mikrodalga ısıtma koşullarında 45-120 dk reaksiyon sürelerinde iyi verimlerle sentezlenmiştir. Sonuçlar göstermiştir ki, organik moleküllerin sentezinde, iyi bir yeşil proses olarak bilinen mikrodalga-destekli sentez, bizim çalışmamızda daha kısa reaksiyon süreleri ve yüksek verimler elde edilebilmesini sağlamıştır. Anahtar kelimeler: Schiff bazı, imidazo[1,2-a]pirimidin, mikrodalga sentez, geleneksel ısıtma. 1. Introduction Nitrogen containing heterocycles are significant inputs of the drug industry since commonly found in synthetic and natural drugs. Among them, the fused heterocyclic cores with pyrimidine ring have a central place due to their exclusive medicinal applications [1]. The synthesis, biological and pharmacological studies on imidazo[1,2- a]pyrimidines which forms the fusion of imidazole and pyrimidine moieties have speeded up in recent days because of their superior medical properties such as anticancer, cardiovascular, antibacterial, antimicrobial, antifungal, antiviral, anti- inflammatory, HIV inhibitor, local anesthetic, kinase inhibitors and their photophysical applications such as biomarkers and photochemical sensors due to their fluorophore properties [2-5]. Fasiplon, taniplon and divaplon are known as anxiolytic and anticonvulsant drugs in the market from the imidazo[1,2-a]pyrimidine drug family [3]. Schiff bases are obtained as a result of the condensation reaction with aldehyde/ketone and aromatic amines. Schiff bases are known as imine compounds containing C=N bond and synthesized the first time in 1869 by German chemist, Hugo Schiff. These compounds are an interesting class because of be stable, easily synthesized and their broad range applications such as biological including anticancer, antioxidant, antimicrobial, antitubercular, antifungal, analgesic, antiinflammatory and material science such as optical computer, photodetector, photostabilizer, solar filter, opto- electronic, electrode, organic battery, electrochromic device and corrosion areas [6-10]. Microwave energy has been using to synthesize various molecules by different type of reactions as an efficient eco-friendly technique since 1980s [11-14]. Microwave-assisted organic synthesis (MAOS) has many advantages over the conventional heating methods such as reduction in the reaction times, improvement in the yields, decreasement the decomposition of reactants and products, enhancement the product purities and selectivity in an environmentally friendly reaction medium [12-14]. However, there are not many examples on the microwave-assisted synthesis of imines in the literature [11, 15-17]. We report herein the conventional and green microwave-asssisted synthesis of a variety of imidazo[1,2-a]pyrimidine derived schiff bases. These compounds may be used for potential biological application in future drug research. 429 BAUN Fen Bil. Enst. Dergisi, 22(2), 428-438, (2020) 2. Material and method 2.1. General Information All chemicals were supplied from commercial sources and used directly in reactions. Microwave synthesis experiments were conducted by using CEM SP Discover Microwave Synthesis Reactor with dynamic mode option. The melting points were determined with X-4 Melting-point Apparatus. Analytical thin-layer chromatography was performed on precoated Kieselgel 60GF254 plates. The spots were visualized by UV light (254 nm) and KMnO4 stain. Silica gel 60 (230-400 mesh, Merck) was used for column chromatography. Perkin Elmer Spectrum 100 FTIR spectrophotometer was used for Infrared spectra by applying ATR techniques. 1H and 13C NMR spectras were obtained by Jeol 400 MHz NMR spectrometer using TMS as internal standard and DMSO-d6 as solvent. The molecular weights of products were determined at Shimadzu LC-MS/MS 8040 Liquid Chromatograph Mass Spectrometer using an ESI source. 2.2. Synthesis and Characterization of S1-S5 General Procedure for Conventional Heating Reactions The mixture of imidazo[1,2-a]pyrimidine-2-carbaldehyde (1.0 equiv.) and aromatic amines (aniline, 4-chloroaniline, 4-aminophenol, 1-naphthylamine and 3,5- difluoroaniline) (1.0 equiv.) were dissolved in appropriate volume of toluene. Magnesium sulfate (1.0 equiv.) was added to the reaction medium and the resulting mixture was refluxed for various reaction times (10-36 h). After completion of the reaction detected by TLC (EtOAc), toluene was evaporated to dryness. DCM was added to the residue, MgSO4 was filtered and washed with DCM. The solvent was concentrated in vacuo. The crude product was purified by using crystallization or column chromatography techniques. General Procedure for Microwave Irradiation Reactions Aldehyde (1.0 equiv.) and aromatic amines (1.0 equiv.) were dissolved in toluene at a 10 mL microwave reaction vessel. MgSO4 (1.0 equiv.) was added and stirred at room temperature for 3 min. The mixture was heated at 120 °C under dynamic mode of microwave irradiation for 45-120 min. After completion of the reaction, the mixture was warmed to room temperature. Same work-up and purification procedures mentioned above were applied. N-(Phenyl)-1-(imidazo[1,2-a]pyrimidin-2-yl)methanimine (S1). The reaction was performed under general procedure conditions as described above, using aldehyde derivative and aniline with 10 h and 60 min reaction times for conventional and microwave heating conditions, respectively. The crude product was purified by column chromatography on silica gel (hexane/ethyl acetate, 1:12) to give compound S1. Yellow solid; 82 and 80% yield (conventional and microwave reactions, respectively); m.p. 172-174°C; IR (ATR) ϑ 3112, 3089, 3060, 3003, 2990, 2949, 2923, 2907, 2869, 2851, 1620, 1607, 1520, 1471, 1404, 1342, 1283, 1277, 1224, 1162, 1140, 1080, 969, 886, -1 1 860, 801, 781, 761, 704 cm ; H NMR (400 MHz, DMSO-d6) δ 10.05 (dd, J=6.82 and 2.09 Hz, 1H), 8.89 (s, 1H), 8.76 (dd, J=4.18 and 2.07 Hz, 1H), 8.39 (s, 1H), 7.44-7.39 (m, 2H), 7.38-7.32 (m, 3H), 7.23 (tt, J=7.28 and 1.19 Hz, 1H); 13C NMR (100 MHz, DMSO-d6) δ 153.21, 151.65, 150.97, 149.96, 144.03, 137.24, 129.84, 126.53, 121.64, + 121.29, 111.50; LC/MS (ESI) m/z: (C13H10N4) 223.0 [M+H] . 430 GÜNGÖR T. N-(4-Chlorophenyl)-1-(imidazo[1,2-a]pyrimidin-2-yl)methanimine (S2). The reaction was performed under general procedure conditions as described above, using aldehyde derivative and 4-chloroaniline with 24 h and 60 min reaction times for conventional and microwave heating conditions, respectively. The crude product was purified by column chromatography on silica gel (ethyl acetate) to give compound S2. Light yellow solid; 46 and 79% yield (conventional and microwave reactions, respectively); m.p. 211-214°C; IR (ATR) ϑ 3100, 3091, 3061, 2948, 2923, 2852, 1619, 1607, 1489, 1479, 1414, 1337, 1284, 1229, 1157, 1085, 1009, 959, 869, 832, 793, 775, -1 1 761, 712, 682 cm ; H NMR (400 MHz, DMSO-d6) δ 10.02 (dd, J= 6.85 and 2.06 Hz, 1H), 8.89 (s, 1H), 8.76 (dd, J= 2.06 Hz, 1H), 8.39 (s, 1H), 7.46 (m, 2H), 7.36 (m, 3H); 13 C NMR (100 MHz, DMSO-d6) δ 153.35, 151.10, 150.53, 150.43, 144.41, 137.34, + 130.68, 129.76, 123.46, 121.21, 111.58; LC/MS (ESI) m/z: (C13H9ClN4) 257.0 [M+H] . N-(4-Hydroxyphenyl)-1-(imidazo[1,2-a]pyrimidin-2-yl)methanimine (S3). The reaction was performed under general procedure conditions as described above, using aldehyde derivative and 4-aminophenol with 18 h and 45 min reaction times for
Load more

Recommended publications
  • )&F1y3x PHARMACEUTICAL APPENDIX to THE
    )&f1y3X PHARMACEUTICAL APPENDIX TO THE HARMONIZED TARIFF SCHEDULE )&f1y3X PHARMACEUTICAL APPENDIX TO THE TARIFF SCHEDULE 3 Table 1. This table enumerates products described by International Non-proprietary Names (INN) which shall be entered free of duty under general note 13 to the tariff schedule. The Chemical Abstracts Service (CAS) registry numbers also set forth in this table are included to assist in the identification of the products concerned. For purposes of the tariff schedule, any references to a product enumerated in this table includes such product by whatever name known. Product CAS No. Product CAS No. ABAMECTIN 65195-55-3 ACTODIGIN 36983-69-4 ABANOQUIL 90402-40-7 ADAFENOXATE 82168-26-1 ABCIXIMAB 143653-53-6 ADAMEXINE 54785-02-3 ABECARNIL 111841-85-1 ADAPALENE 106685-40-9 ABITESARTAN 137882-98-5 ADAPROLOL 101479-70-3 ABLUKAST 96566-25-5 ADATANSERIN 127266-56-2 ABUNIDAZOLE 91017-58-2 ADEFOVIR 106941-25-7 ACADESINE 2627-69-2 ADELMIDROL 1675-66-7 ACAMPROSATE 77337-76-9 ADEMETIONINE 17176-17-9 ACAPRAZINE 55485-20-6 ADENOSINE PHOSPHATE 61-19-8 ACARBOSE 56180-94-0 ADIBENDAN 100510-33-6 ACEBROCHOL 514-50-1 ADICILLIN 525-94-0 ACEBURIC ACID 26976-72-7 ADIMOLOL 78459-19-5 ACEBUTOLOL 37517-30-9 ADINAZOLAM 37115-32-5 ACECAINIDE 32795-44-1 ADIPHENINE 64-95-9 ACECARBROMAL 77-66-7 ADIPIODONE 606-17-7 ACECLIDINE 827-61-2 ADITEREN 56066-19-4 ACECLOFENAC 89796-99-6 ADITOPRIM 56066-63-8 ACEDAPSONE 77-46-3 ADOSOPINE 88124-26-9 ACEDIASULFONE SODIUM 127-60-6 ADOZELESIN 110314-48-2 ACEDOBEN 556-08-1 ADRAFINIL 63547-13-7 ACEFLURANOL 80595-73-9 ADRENALONE
    [Show full text]
  • G Genito Urinary System and Sex Hormones
    WHO/EMP/RHT/TSN/2018.2 © World Health Organization 2018 Some rights reserved. This work is available under the Creative Commons Attribution-NonCommercial-ShareAlike 3.0 IGO licence (CC BY-NC-SA 3.0 IGO; https://creativecommons.org/licenses/by-nc-sa/3.0/igo). Under the terms of this licence, you may copy, redistribute and adapt the work for non-commercial purposes, provided the work is appropriately cited, as indicated below. In any use of this work, there should be no suggestion that WHO endorses any specific organization, products or services. The use of the WHO logo is not permitted. If you adapt the work, then you must license your work under the same or equivalent Creative Commons licence. If you create a translation of this work, you should add the following disclaimer along with the suggested citation: “This translation was not created by the World Health Organization (WHO). WHO is not responsible for the content or accuracy of this translation. The original English edition shall be the binding and authentic edition”. Any mediation relating to disputes arising under the licence shall be conducted in accordance with the mediation rules of the World Intellectual Property Organization. Suggested citation. Learning clinical pharmacology with the use of INNs and their stems. Geneva: World Health Organization; 2018 (WHO/EMP/RHT/TSN/2018.2). Licence: CC BY-NC-SA 3.0 IGO. Cataloguing-in-Publication (CIP) data. CIP data are available at http://apps.who.int/iris. Sales, rights and licensing. To purchase WHO publications, see http://apps.who.int/bookorders. To submit requests for commercial use and queries on rights and licensing, see http://www.who.int/about/licensing.
    [Show full text]
  • WO 2015/072852 Al 21 May 2015 (21.05.2015) P O P C T
    (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 WO 2015/072852 Al 21 May 2015 (21.05.2015) P O P C T (51) International Patent Classification: (81) Designated States (unless otherwise indicated, for every A61K 36/84 (2006.01) A61K 31/5513 (2006.01) kind of national protection available): AE, AG, AL, AM, A61K 31/045 (2006.01) A61P 31/22 (2006.01) AO, AT, AU, AZ, BA, BB, BG, BH, BN, BR, BW, BY, A61K 31/522 (2006.01) A61K 45/06 (2006.01) BZ, CA, CH, CL, CN, CO, CR, CU, CZ, DE, DK, DM, DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, (21) International Application Number: HN, HR, HU, ID, IL, IN, IR, IS, JP, KE, KG, KN, KP, KR, PCT/NL20 14/050780 KZ, LA, LC, LK, LR, LS, LU, LY, MA, MD, ME, MG, (22) International Filing Date: MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, OM, 13 November 2014 (13.1 1.2014) 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, (25) Filing Language: English TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW. (26) Publication Language: English (84) Designated States (unless otherwise indicated, for every (30) Priority Data: kind of regional protection available): ARIPO (BW, GH, 61/903,430 13 November 2013 (13. 11.2013) US GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, ST, SZ, TZ, UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, RU, (71) Applicant: RJG DEVELOPMENTS B.V.
    [Show full text]
  • Pharmaceuticals Appendix
    )&f1y3X PHARMACEUTICAL APPENDIX TO THE HARMONIZED TARIFF SCHEDULE )&f1y3X PHARMACEUTICAL APPENDIX TO THE TARIFF SCHEDULE 3 Table 1. This table enumerates products described by International Non-proprietary Names (INN) which shall be entered free of duty under general note 13 to the tariff schedule. The Chemical Abstracts Service (CAS) registry numbers also set forth in this table are included to assist in the identification of the products concerned. For purposes of the tariff schedule, any references to a product enumerated in this table includes such product by whatever name known. Product CAS No. Product CAS No. ABAMECTIN 65195-55-3 ADAPALENE 106685-40-9 ABANOQUIL 90402-40-7 ADAPROLOL 101479-70-3 ABECARNIL 111841-85-1 ADEMETIONINE 17176-17-9 ABLUKAST 96566-25-5 ADENOSINE PHOSPHATE 61-19-8 ABUNIDAZOLE 91017-58-2 ADIBENDAN 100510-33-6 ACADESINE 2627-69-2 ADICILLIN 525-94-0 ACAMPROSATE 77337-76-9 ADIMOLOL 78459-19-5 ACAPRAZINE 55485-20-6 ADINAZOLAM 37115-32-5 ACARBOSE 56180-94-0 ADIPHENINE 64-95-9 ACEBROCHOL 514-50-1 ADIPIODONE 606-17-7 ACEBURIC ACID 26976-72-7 ADITEREN 56066-19-4 ACEBUTOLOL 37517-30-9 ADITOPRIME 56066-63-8 ACECAINIDE 32795-44-1 ADOSOPINE 88124-26-9 ACECARBROMAL 77-66-7 ADOZELESIN 110314-48-2 ACECLIDINE 827-61-2 ADRAFINIL 63547-13-7 ACECLOFENAC 89796-99-6 ADRENALONE 99-45-6 ACEDAPSONE 77-46-3 AFALANINE 2901-75-9 ACEDIASULFONE SODIUM 127-60-6 AFLOQUALONE 56287-74-2 ACEDOBEN 556-08-1 AFUROLOL 65776-67-2 ACEFLURANOL 80595-73-9 AGANODINE 86696-87-9 ACEFURTIAMINE 10072-48-7 AKLOMIDE 3011-89-0 ACEFYLLINE CLOFIBROL 70788-27-1
    [Show full text]
  • The Use of Stems in the Selection of International Nonproprietary Names (INN) for Pharmaceutical Substances
    WHO/PSM/QSM/2006.3 The use of stems in the selection of International Nonproprietary Names (INN) for pharmaceutical substances 2006 Programme on International Nonproprietary Names (INN) Quality Assurance and Safety: Medicines Medicines Policy and Standards The use of stems in the selection of International Nonproprietary Names (INN) for pharmaceutical substances FORMER DOCUMENT NUMBER: WHO/PHARM S/NOM 15 © World Health Organization 2006 All rights reserved. Publications of the World Health Organization can be obtained from WHO Press, World Health Organization, 20 Avenue Appia, 1211 Geneva 27, Switzerland (tel.: +41 22 791 3264; fax: +41 22 791 4857; e-mail: [email protected]). Requests for permission to reproduce or translate WHO publications – whether for sale or for noncommercial distribution – should be addressed to WHO Press, at the above address (fax: +41 22 791 4806; e-mail: [email protected]). The designations employed and the presentation of the material in this publication do not imply the expression of any opinion whatsoever on the part of the World Health Organization concerning the legal status of any country, territory, city or area or of its authorities, or concerning the delimitation of its frontiers or boundaries. Dotted lines on maps represent approximate border lines for which there may not yet be full agreement. The mention of specific companies or of certain manufacturers’ products does not imply that they are endorsed or recommended by the World Health Organization in preference to others of a similar nature that are not mentioned. Errors and omissions excepted, the names of proprietary products are distinguished by initial capital letters.
    [Show full text]
  • (12) Patent Application Publication (10) Pub. No.: US 2009/0005722 A1 Jennings-Spring (43) Pub
    US 20090005722A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2009/0005722 A1 Jennings-Spring (43) Pub. Date: Jan. 1, 2009 (54) SKIN-CONTACTING-ADHESIVE FREE Publication Classification DRESSING (51) Int. Cl. Inventor: Barbara Jennings-Spring, Jupiter, A61N L/30 (2006.01) (76) A6F I3/00 (2006.01) FL (US) A6IL I5/00 (2006.01) Correspondence Address: AOIG 7/06 (2006.01) Irving M. Fishman AOIG 7/04 (2006.01) c/o Cohen, Tauber, Spievack and Wagner (52) U.S. Cl. .................. 604/20: 602/43: 602/48; 4771.5; Suite 2400, 420 Lexington Avenue 47/13 New York, NY 10170 (US) (57) ABSTRACT (21) Appl. No.: 12/231,104 A dressing having a flexible sleeve shaped to accommodate a Substantially cylindrical body portion, the sleeve having a (22) Filed: Aug. 29, 2008 lining which is substantially non-adherent to the body part being bandaged and having a peripheral securement means Related U.S. Application Data which attaches two peripheral portions to each other without (63) Continuation-in-part of application No. 1 1/434,689, those portions being circumferentially adhered to the sleeve filed on May 16, 2006. portion. Patent Application Publication Jan. 1, 2009 Sheet 1 of 9 US 2009/0005722 A1 Patent Application Publication Jan. 1, 2009 Sheet 2 of 9 US 2009/0005722 A1 10 8 F.G. 5 Patent Application Publication Jan. 1, 2009 Sheet 3 of 9 US 2009/0005722 A1 13 FIG.6 2 - Y TIII Till "T fift 11 10 FIG.7 8 13 6 - 12 - Timir" "in "in "MINIII.
    [Show full text]
  • WO 2015/072853 Al 21 May 2015 (21.05.2015) P O P C T
    (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 WO 2015/072853 Al 21 May 2015 (21.05.2015) P O P C T (51) International Patent Classification: (81) Designated States (unless otherwise indicated, for every A61K 45/06 (2006.01) A61K 31/5513 (2006.01) kind of national protection available): AE, AG, AL, AM, A61K 31/045 (2006.01) A61K 31/5517 (2006.01) AO, AT, AU, AZ, BA, BB, BG, BH, BN, BR, BW, BY, A61K 31/522 (2006.01) A61P 31/22 (2006.01) BZ, CA, CH, CL, CN, CO, CR, CU, CZ, DE, DK, DM, A61K 31/551 (2006.01) DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, HN, HR, HU, ID, IL, IN, IR, IS, JP, KE, KG, KN, KP, KR, (21) International Application Number: KZ, LA, LC, LK, LR, LS, LU, LY, MA, MD, ME, MG, PCT/NL20 14/050781 MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, OM, (22) International Filing Date: PA, PE, PG, PH, PL, PT, QA, RO, RS, RU, RW, SA, SC, 13 November 2014 (13.1 1.2014) SD, SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW. (25) Filing Language: English (84) Designated States (unless otherwise indicated, for every (26) Publication Language: English kind of regional protection available): ARIPO (BW, GH, (30) Priority Data: GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, ST, SZ, 61/903,433 13 November 2013 (13.
    [Show full text]
  • Pharmaceutical Appendix to the Tariff Schedule 2
    Harmonized Tariff Schedule of the United States (2007) (Rev. 2) Annotated for Statistical Reporting Purposes PHARMACEUTICAL APPENDIX TO THE HARMONIZED TARIFF SCHEDULE Harmonized Tariff Schedule of the United States (2007) (Rev. 2) Annotated for Statistical Reporting Purposes PHARMACEUTICAL APPENDIX TO THE TARIFF SCHEDULE 2 Table 1. This table enumerates products described by International Non-proprietary Names (INN) which shall be entered free of duty under general note 13 to the tariff schedule. The Chemical Abstracts Service (CAS) registry numbers also set forth in this table are included to assist in the identification of the products concerned. For purposes of the tariff schedule, any references to a product enumerated in this table includes such product by whatever name known. ABACAVIR 136470-78-5 ACIDUM LIDADRONICUM 63132-38-7 ABAFUNGIN 129639-79-8 ACIDUM SALCAPROZICUM 183990-46-7 ABAMECTIN 65195-55-3 ACIDUM SALCLOBUZICUM 387825-03-8 ABANOQUIL 90402-40-7 ACIFRAN 72420-38-3 ABAPERIDONUM 183849-43-6 ACIPIMOX 51037-30-0 ABARELIX 183552-38-7 ACITAZANOLAST 114607-46-4 ABATACEPTUM 332348-12-6 ACITEMATE 101197-99-3 ABCIXIMAB 143653-53-6 ACITRETIN 55079-83-9 ABECARNIL 111841-85-1 ACIVICIN 42228-92-2 ABETIMUSUM 167362-48-3 ACLANTATE 39633-62-0 ABIRATERONE 154229-19-3 ACLARUBICIN 57576-44-0 ABITESARTAN 137882-98-5 ACLATONIUM NAPADISILATE 55077-30-0 ABLUKAST 96566-25-5 ACODAZOLE 79152-85-5 ABRINEURINUM 178535-93-8 ACOLBIFENUM 182167-02-8 ABUNIDAZOLE 91017-58-2 ACONIAZIDE 13410-86-1 ACADESINE 2627-69-2 ACOTIAMIDUM 185106-16-5 ACAMPROSATE 77337-76-9
    [Show full text]
  • Marrakesh Agreement Establishing the World Trade Organization
    No. 31874 Multilateral Marrakesh Agreement establishing the World Trade Organ ization (with final act, annexes and protocol). Concluded at Marrakesh on 15 April 1994 Authentic texts: English, French and Spanish. Registered by the Director-General of the World Trade Organization, acting on behalf of the Parties, on 1 June 1995. Multilat ral Accord de Marrakech instituant l©Organisation mondiale du commerce (avec acte final, annexes et protocole). Conclu Marrakech le 15 avril 1994 Textes authentiques : anglais, français et espagnol. Enregistré par le Directeur général de l'Organisation mondiale du com merce, agissant au nom des Parties, le 1er juin 1995. Vol. 1867, 1-31874 4_________United Nations — Treaty Series • Nations Unies — Recueil des Traités 1995 Table of contents Table des matières Indice [Volume 1867] FINAL ACT EMBODYING THE RESULTS OF THE URUGUAY ROUND OF MULTILATERAL TRADE NEGOTIATIONS ACTE FINAL REPRENANT LES RESULTATS DES NEGOCIATIONS COMMERCIALES MULTILATERALES DU CYCLE D©URUGUAY ACTA FINAL EN QUE SE INCORPOR N LOS RESULTADOS DE LA RONDA URUGUAY DE NEGOCIACIONES COMERCIALES MULTILATERALES SIGNATURES - SIGNATURES - FIRMAS MINISTERIAL DECISIONS, DECLARATIONS AND UNDERSTANDING DECISIONS, DECLARATIONS ET MEMORANDUM D©ACCORD MINISTERIELS DECISIONES, DECLARACIONES Y ENTEND MIENTO MINISTERIALES MARRAKESH AGREEMENT ESTABLISHING THE WORLD TRADE ORGANIZATION ACCORD DE MARRAKECH INSTITUANT L©ORGANISATION MONDIALE DU COMMERCE ACUERDO DE MARRAKECH POR EL QUE SE ESTABLECE LA ORGANIZACI N MUND1AL DEL COMERCIO ANNEX 1 ANNEXE 1 ANEXO 1 ANNEX
    [Show full text]
  • Federal Register / Vol. 60, No. 80 / Wednesday, April 26, 1995 / Notices DIX to the HTSUS—Continued
    20558 Federal Register / Vol. 60, No. 80 / Wednesday, April 26, 1995 / Notices DEPARMENT OF THE TREASURY Services, U.S. Customs Service, 1301 TABLE 1.ÐPHARMACEUTICAL APPEN- Constitution Avenue NW, Washington, DIX TO THE HTSUSÐContinued Customs Service D.C. 20229 at (202) 927±1060. CAS No. Pharmaceutical [T.D. 95±33] Dated: April 14, 1995. 52±78±8 ..................... NORETHANDROLONE. A. W. Tennant, 52±86±8 ..................... HALOPERIDOL. Pharmaceutical Tables 1 and 3 of the Director, Office of Laboratories and Scientific 52±88±0 ..................... ATROPINE METHONITRATE. HTSUS 52±90±4 ..................... CYSTEINE. Services. 53±03±2 ..................... PREDNISONE. 53±06±5 ..................... CORTISONE. AGENCY: Customs Service, Department TABLE 1.ÐPHARMACEUTICAL 53±10±1 ..................... HYDROXYDIONE SODIUM SUCCI- of the Treasury. NATE. APPENDIX TO THE HTSUS 53±16±7 ..................... ESTRONE. ACTION: Listing of the products found in 53±18±9 ..................... BIETASERPINE. Table 1 and Table 3 of the CAS No. Pharmaceutical 53±19±0 ..................... MITOTANE. 53±31±6 ..................... MEDIBAZINE. Pharmaceutical Appendix to the N/A ............................. ACTAGARDIN. 53±33±8 ..................... PARAMETHASONE. Harmonized Tariff Schedule of the N/A ............................. ARDACIN. 53±34±9 ..................... FLUPREDNISOLONE. N/A ............................. BICIROMAB. 53±39±4 ..................... OXANDROLONE. United States of America in Chemical N/A ............................. CELUCLORAL. 53±43±0
    [Show full text]
  • Stembook 2018.Pdf
    The use of stems in the selection of International Nonproprietary Names (INN) for pharmaceutical substances FORMER DOCUMENT NUMBER: WHO/PHARM S/NOM 15 WHO/EMP/RHT/TSN/2018.1 © World Health Organization 2018 Some rights reserved. This work is available under the Creative Commons Attribution-NonCommercial-ShareAlike 3.0 IGO licence (CC BY-NC-SA 3.0 IGO; https://creativecommons.org/licenses/by-nc-sa/3.0/igo). Under the terms of this licence, you may copy, redistribute and adapt the work for non-commercial purposes, provided the work is appropriately cited, as indicated below. In any use of this work, there should be no suggestion that WHO endorses any specific organization, products or services. The use of the WHO logo is not permitted. If you adapt the work, then you must license your work under the same or equivalent Creative Commons licence. If you create a translation of this work, you should add the following disclaimer along with the suggested citation: “This translation was not created by the World Health Organization (WHO). WHO is not responsible for the content or accuracy of this translation. The original English edition shall be the binding and authentic edition”. Any mediation relating to disputes arising under the licence shall be conducted in accordance with the mediation rules of the World Intellectual Property Organization. Suggested citation. The use of stems in the selection of International Nonproprietary Names (INN) for pharmaceutical substances. Geneva: World Health Organization; 2018 (WHO/EMP/RHT/TSN/2018.1). Licence: CC BY-NC-SA 3.0 IGO. Cataloguing-in-Publication (CIP) data.
    [Show full text]
  • Customs Tariff - Schedule
    CUSTOMS TARIFF - SCHEDULE 99 - i Chapter 99 SPECIAL CLASSIFICATION PROVISIONS - COMMERCIAL Notes. 1. The provisions of this Chapter are not subject to the rule of specificity in General Interpretative Rule 3 (a). 2. Goods which may be classified under the provisions of Chapter 99, if also eligible for classification under the provisions of Chapter 98, shall be classified in Chapter 98. 3. Goods may be classified under a tariff item in this Chapter and be entitled to the Most-Favoured-Nation Tariff or a preferential tariff rate of customs duty under this Chapter that applies to those goods according to the tariff treatment applicable to their country of origin only after classification under a tariff item in Chapters 1 to 97 has been determined and the conditions of any Chapter 99 provision and any applicable regulations or orders in relation thereto have been met. 4. The words and expressions used in this Chapter have the same meaning as in Chapters 1 to 97. Issued January 1, 2020 99 - 1 CUSTOMS TARIFF - SCHEDULE Tariff Unit of MFN Applicable SS Description of Goods Item Meas. Tariff Preferential Tariffs 9901.00.00 Articles and materials for use in the manufacture or repair of the Free CCCT, LDCT, GPT, following to be employed in commercial fishing or the commercial UST, MXT, CIAT, CT, harvesting of marine plants: CRT, IT, NT, SLT, PT, COLT, JT, PAT, HNT, Artificial bait; KRT, CEUT, UAT, CPTPT: Free Carapace measures; Cordage, fishing lines (including marlines), rope and twine, of a circumference not exceeding 38 mm; Devices for keeping nets open; Fish hooks; Fishing nets and netting; Jiggers; Line floats; Lobster traps; Lures; Marker buoys of any material excluding wood; Net floats; Scallop drag nets; Spat collectors and collector holders; Swivels.
    [Show full text]