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|||||||||||||| O US005399584A United States Patent 19) 11 Patent Number: 5,399,584 Ares et al. 45) Date of Patent: Mar. 21, 1995 (54 USE OF FLAVONEDERIVATIVES FOR 75308 2/1982 Romania. GASTROPROTECTION 90578 11/1986 Romania . 75 Inventors: Jeffrey J. Ares, Hamilton, Ohio; 555888 5/1977 U.S.S.R. Sunil V. Kakodkar, Bethlehem, Pa.; OTHER PUBLICATIONS Gary R. Kelm, Cincinnati; Peter D. Remington's Pharmaceutical Sciences, 16th edition, Murray, Fairfield, both of Ohio; (1980) p. 431. Jared L. Randall, Plymouth, N.Y.; Alcaraz, M. J. & J. R. S. Hoult, "Actions of Flavonoids Candice L. Slough, Middletown, and the Novel Anti-Inflammatory Flavone, Hypola Ohio etin-8-Glucoside, on Prostaglandin Biosynthesis and 73) Assignee: The Procter & Gamble Company, Glucoside, on Prostaglandin Biosynthesis and Inactiva Cincinnati, Ohio (List continued on next page.) (21) Appl. No.: 15,771 Primary Examiner-Raymond J. Henley, III ar. Attorney, Agent, or Firm-David L. Suter; Jacobus C. (22 Filed: Feb. 10, 1993 Rasser; Milton B. Graff, IV Related U.S. Application Data 57) ABSTRACT 63 Continuation-in-part of Ser. No. 878,582, May 5, 1992, The subject invention relates to methods for preventing abandoned. or treating damage to the mucosal lining of the gastroin 51) Int. Cl. ..................... A61K 31/38; A61K31/35; testinal tract of a human or lower animal by administer- A61K 31/19; A61K 31/40; A61K 49/00 E. ad effective amount of a compound having (52) U.S.C. .................................... 514/432; 514/413; 514/456; 514/570; 514/922; 514/925; 514/926; 514/927; 424/10 58 Field of Search ............... 514/432, 456, 925, 926, 514/927, 434, 570, 413,922; 424/10 56) References Cited U.S. PATENT DOCUMENTS 3,155,579 il/1964 Perrault................................. 167/65 3,495,009 2/1970 Tronche ... 514/456 4,707,360 1 1/1987 Brasey ....... 54/.456 4,891,356 l/1990 Szabo ...................................... 514/2 5,106,871 4/1992 Komazawa et al. ................ 514/571 wherein X and Y are each independently selected from FOREIGN PATENT DOCUMENTS O and S; R1 y R2 and R3 are each independently selected from hydrogen, hydroxy, halo, unsubstituted or mono 88.8982 9/1981 Belgium . substituted straight or branched C1-C4 alkanyl, and E. 1/33; Epean Pat. Off. unsubstituted or substituted straight or branched C1-C4 48-42448 4/1973 Japan.apan . alkanoxy;- and each 1of R2 R', R5, R63. and R7 is hydrogen or, 48-99312 12/1973 Japan. if one or more of R, R2 and R3 is other than hydrogen, 48-99313 12/1973 Japan . each of R, R, R and R is selected from hydrogen, 51-23268 2/1976 Japan. halo, trifluoromethyl, and unsubstituted straight or 55-27112 2/1980 Japan. branched C1-C4 alkanyl. 55-143913 11/1980 Japan. 3-5424 1/1991 Japan . 19 Claims, No Drawings 5,399,584 Page 2 OTHER PUBLICATIONS Ciaceri, G. & G. Attaguile, "Effects of Luteolin, Apige tion', Biochemical Pharmacology, vol. 34, No. 14 nin, and Acacetin on Experimentally Induced Gastric Ulcer', Minerva Med., vol. 63, No. 29 (1972), pp. (1985), pp. 2477-2482. 1665-668. Arakawa, T., A. Nakamura, H. Yamada, H. Nebiki, H. Corvazier, E. & J. Maclouf, "Interference of Some Satoh, T. Fukoda & K. Kobayashi, "Protection of Gas Flavonoids and Non-Steroidal Anti-Inflammatory tric Surface Epithelial Cells of Rats by 16, 16-Dimethyl Drugs with Oxidative Metabolism of Arachidonic Acid Prostaglandin E2 and Sofalcone, a Synthetic Flavonoid by Human Platelets and Neutrophils', Biochimica et Derivative of Sophoradin, against Ethanol', Digestion, Biophysica Acta, vol. 835 (1985), pp. 315-321. vol. 41 (1988), pp. 61-67. Cristoni, A., S. Malandrino & M.J. Magistretti, “Effect Barnaulov, O. D., O. A. Manicheva, G. G. Zapesoch of a Natural Flavonoid on Gastric Mucosal Barrier', naya, V. L. Shelyuto & V. I. Glyzin, “Effect of Some Arzneim-Forsch., vol.39(I), No. 5 (1989), pp. 590-592. Flavonoids on the Ulcerogenic Activity of Reserpine in Gabor, M. & A. Kekes-Szabo, "Effect of Bioflavoids in Mice', Khim.-Farm. Zh., vol. 16, No. 3 (1982), pp. Experimental Gastric Ulcer', Kiserletes Orvos 300-303. , tudomany, vol. 24, (1972), pp. 1-4. Barnaulov, O. D., O. A. Manicheva & P. P. Denisenko, Goel, R. K. V. B. Pandey, S. P. D. Dwivedi & Y. V. “A Method for Evaluating the Effect of Drugs on the Rao “Antiinflammatory and Anti-Ulcer Effects of Ka Ulcerogenic Activity of Reserpine in Mice”, Farmakol. empferol, a Flavone, isolated from Rhamnus procumb Toksikol. (Moscow), vol. 45, No. 4 (1982), pp. 105-110. ens', Indian Journal of Experimental Biology, vol. 26 Barnaulov, O. D., O. A. Manicheva & N. F. Komis (Feb. 1988), pp. 121-124. sarenko, "Comparative Evaluation of the Effect of Hatamaya, K. S. Yokomori, Y. Kawashina, R. Saziki & Some Flavonoids on Changes in the Gastric Wall of K. Kyogoku, "Anti-Ulcer Effect of Isoprenyl Flavo Reserpine-Treated or Immobilized Mice', Khim.-K- noids. III. Synthesis and Anti-Ulcer Activity of Metab him. Zh., vol. 17, No. 8 (1983), pp. 946-951. olites of 2'Carboxymethoxy-4,4'-bis(3-me Barnaulov, O. D., O.A. Manicheva, V. L. Shelyuto, M. thyl-2-butenyloxy)chalcone' Chemical & Pharmaceu M. Konopleva & V. I. Glyzin, "Effect of Flavonoids on tical Bulletin, vol. 33, No. 4 (Apr., 1985)), 1327-1333. the Development of Experimental Stomach Dystrophy Ilarionov, I., L. Rainova & N. Nakov, “On the Antin in Mice', Khim.-Far. Zh., vol. 18, No. 8 (1984), pp. flammatory and Antiulcer Activity of Some Flavonoids 935-941. Isolated from the Genus Genista L., Farmatsiya (So Barnaulov, O. D., O. A. Manicheva, I. I. Chemesova & fia), vol. 29, No. 6 (1979), pp. 39-46. N. F. Komissarenko, "Comparative Evaluation of the Konturek, S.J., M. E. Kitler, T. Brzozowski & T. Ra Effect of Flavonoids on the Development of Experi decki, "Gastric Protection by Meciadanol-A New mental Lesions of the Mouse Stomach', Khim.-Farm. Synthetic Flavonoid-Inhibiting Histidine Decarboxyl Zh., vol. 18, No. 11 (1984), pp. 1330-1333. ase', Digestive Diseases and Sciences, vol. 31, No. 8 Barnaulov, O. D., O. A. Manicheva, R. K. Yakovlev, (Aug. 1986), pp. 847-852. “Evaluation of the Effects of Flavonoids from the Ae Konturek, S.J., T. Radecki, T. Brzozowski, D. Droz rial Parts of Astragalus Quisqualis Bunge and A. Floc dowicz, I. Piastucki, M. Muramatsu, M. Tanaka & H. cosifolius Sumn. on the Development of Experiemntal Aihara, "Antiulcer and Gastroprotective Effects of Lesions in the Mouse Stomach', Rastit. Resur., vol. 21, Solon, a Synthetic Flavonoid Derivative of Sophora No. 1 (1985), pp. 85-90. din. Role of Endogenous Protaglandins”, European Boughton-Smith, N. K. & B. J. R. Whittle, “Failure of Journal of Pharmacology, vol. 125, (1986), pp. 185-192. the Inhibition of Rat Gastric Mucosal 5-Lipoxygenase Konturek, S.J., T. Mrzozowski, D. Drozdowicz, W. by Novel Acetohydroxamic Acids to Prevent Pawlik, & R. Sendur, "Gastro-protective and Ulcer Ethanol-induced Damage', British Journal of Pharma Healing Effects of Sonon, A Synthetic Flavonoid De cology, vol. 95 (1988), pp. 155-162. rivative of Sophoradin', Hepato-Gastroenterology, Brasseur, T., "Proprietes Anti-inflammatoires de Fla vol. 34 (1987, pp. 164-170. Prostaglandins, European vonoides, J. Pharm. Belg., vol. 44, No. 3 (1989), pp. Journal of Pharmacology, vol. 125, (1986), pp. 185 235-241. (List continued on next page.) 5,399,584 Page 3 OTHER PUBLICATIONS hibitor in Rats', Agents and Actions, vol. 15, No/ 3/4 Kyogoku, K., K. Hatayama, S. Yokomori, R. Saziki, S. (1984), pp. 143-145. Nakane, M. Sasajima, J. Sawada, M. Ohzeki & I. Ta Pfister, J. R., W. E. Wymann, M. E. Schuler & A. P. naka, “Anti-ulcer Effect of Isoprenyl Flavonoids, II. Roskowski, "Inhibition of Histamine-Induced Gastric Synthesis and Anti-ulcer Activity of New Chalcones Secretion by Flavone-6-carboxylic Acids', J. Med. Related to Sophoradin', Chemical & Pharmaceutical Chem., vol. 23 (1980, pp. 335-338. Bulletin, vol. 27, No. 12 (1979), pp. 2943-2953. Rainova, L., N. Nakov, S. Bogdanova, E. Minkov & D. Lin, Y. L. & S. Y. Hsu, "The Constituents of the Anti Staneva-Stoicheva, "Ulcero-protective Activity of the ulcer Fractions of Euphorbia Hirta', The Chinese Phar Flavonoids of Genista Rumelica ” Vel. Phytotherapy maceutical Journal, vol. 40, No. 1 (1988), pp. 49-51. Research, vol. 2, No. 3 (1988), pp. 137-139. Martin, M. J., C. Alarcon de la Lastra, E. Marhuenda, Selenina, L. V., R. N. Zozulya & T. N. Yakovleva, F. Delgado & J. Torreblanca, "Anti-ulcergenicity of “Polyphenols of Potentilla Erecta and Their Biological the Flavonoid Fraction from Dittrichia viscosa (L.) W. Activity', Rast. Resur., vol. 9, No. 3 (1973), pp. Greuter in Rats', Pythotherapy Research, vol. 2, No. 4 409-414. (1988), pp. 183-186. Tariq, M., N. S. Parmar, A. M. Ageel, I. A. Al-Meshal Martindale The Extra Pharmacopoeia, 28th Ed., p. & A. R. Abu-Jayyab, "The Gastric Anti-Ulcer Activ 1704, Item 12667-x (1983). ity of Khat (Catha edulis Forsk): Investigations on its Middleton, E. & G. Drzewiecki, "Flavonoid Inhibition Flavonoid Fraction', Research Communications in of Human Basophil Histamine Release Stimulated by Substances Abuse, vol. 5, No. 2 (1984), pp. 157-160. Various Agents', Biochemical Pharmacology, vol. 33, Villar, A., M. A. Gasco & M.J. Alcaraz, "Anti-inflam No. 21 (1984), pp. 3333-3338. matory and Anti-ulcer Properties of Hypolaetin-8- Mower, R. L., R. Landolfi & Steiner, "Inhibiiton. In glucoside, a Novel Plant Flavonoid’, J. Pharm. Phar Vitro of Platelet Aggregation and Arachidonic Acid macol., vol. 36 (1984), pp. 820-823. Metabolism by Flavone', Biochemical Pharmacology, Viswanthan, S., P. Kulanthaivel, S. K. Nazimudeen, T. vol. 33, No. 3, (1984), pp. 357-363. Vinayakan, C. Gopalakrishnan & L. Kameswaran, Obolentseva, G. V. & Y. I. Khadzhai, "Pharmacologi “The Effect of Apigenin 7,4'-Di-O-Methyl Ether, a cal Data on Certain Aspects of the Action of Licorice Flavone from Andrographis Paniculata on Experimen (Glycyrrhiza Glabra) Flavonoids', Vop.
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    ÓÄÊ 612.325:615.322]-084 Zayachkivska O. S., Konturek S.J., Drozdowicz D., Brzozowski T., Gzhegotsky M.R. Influence of plant-originated gastroprotective and antiulcer substances on gastric mucosal repair (review of literature and own data)  îãëÿä³ ë³òåðàòóðè ïðåäñòàâëåíî ñó÷àñíèé ïîãëÿä íà ôóíêö³îíàëüí³ ìîæëèâîñò³ ãàñòðîïðîòåêòîðíèõ ³ ïðîòèâèðàçêîâèõ ðå÷îâèí ðîñëèííîãî ïîõîäæåííÿ.  îñíîâ³ ³íòåðåñó äî ö³º¿ ãðóïè ðå÷îâèí ðîñëèííîãî ïîõîäæåííÿ ëåæàòü äàí³ ïðî ¿õíþ âèðàæåíó çàõèñíó ä³þ, ùî ðåàë³çóºòüñÿ ó â³äíîâëåíí³ ñëèçîâî¿ îáîëîíêè øëóíêà ÷åðåç åêñïðåñ³þ ð³çíîìàí³òíèõ ôàêòîð³â ðîñòó, ñóïðåñ³¿ íåéòðîô³ë/öèòîê³í³íîâîãî êàñêàäó ó òðàâí³é ñèñòåì³, âïëèâ³ íà ñêåâ³íäæ ðåàêö³¿, ïðîÿâëÿþ÷è àíòèîêñèäàíòíó, àíòèíóêëåîë³òè÷íó òà àíòèêàíöåðîãåííó 䳿, ãàëüìóþ÷è àêòèâí³ñòü öèòîõðîìó Ð-450. Äîñë³äæåíî öèòîïðîòåêòîðí³ âëàñòèâîñò³ åêñòðàêò³â ñîôàðàäèíó (ñîëîí), íàñ³ííÿ àìàðàíòó òà ãðåéïôðóòîâèõ çåðíÿòîê çà óìîâ åêñïåðèìåíòàëüíîãî óðàæåííÿ ñëèçîâî¿ øëóíêà 100%-ì åòàíîëîì. Îòðèìàí³ ðåçóëüòàòè ñâ³ä÷àòü ïðî âèðàæåí³ ãàñòðîïðîòåêòîðí³ âëàñòèâîñò³ äîñë³äæóâàíèõ ðå÷îâèí ³ äîö³ëüí³ñòü ¿õíüîãî çàñòîñóâàííÿ ó ïðîô³ëàêòèö³ òà òåðàﳿ ãàñòðîåíòåðîëîã³÷íèõ õâîðîá. INTRODUCTION and known to account for gastroprotection by various irritants and ulcerogens [2, 15, 16, 38]. All mucosal layers play a role as a barrier that This article overviews the potential role limits exposure of the gastric mucosal cells to and also some basic mechanisms of plant- numerous injurious luminal agents. Mucosal originated gastroprotective substances applied surface epithelium is a subject of attack by intragastrically (ig). Recent studies found that physical, chemical or microbiological agents different substances from plant sources, not from the gastric lumen, which are involved in only afford gastroprotection, but also facili- multiple pathologies, such as gastritis, peptic tate ulcer healing.
  • In Silico, in Vitro and in Vivo Memory Enhancing Activity

    In Silico, in Vitro and in Vivo Memory Enhancing Activity

    IN SILICO, IN VITRO AND IN VIVO MEMORY ENHANCING ACTIVITY OF CERTAIN COMMERCIALLY AVAILABLE FLAVONOIDS IN SCOPOLAMINE AND ALUMINIUM-INDUCED LEARNING IMPAIRMENT IN MICE Thesis submitted to The Tamil Nadu Dr. M.G.R. Medical University, Chennai for the award of the degree of DOCTOR OF PHILOSOPHY in PHARMACY Submitted by A. MADESWARAN, M. Pharm., Under the guidance of Dr. K. ASOK KUMAR, M. Pharm., Ph.D. College of Pharmacy, Sri Ramakrishna Institute of Paramedical Sciences, Coimbatore – 641 044, Tamil Nadu, India. JUNE 2017 Certificate This is to certify that the Ph.D. dissertation entitled “IN SILICO, IN VITRO AND IN VIVO MEMORY ENHANCING ACTIVITY OF CERTAIN COMMERCIALLY AVAILABLE FLAVONOIDS IN SCOPOLAMINE AND ALUMINIUM- INDUCED LEARNING IMPAIRMENT IN MICE” being submitted to The Tamil Nadu Dr. M.G.R. Medical University, Chennai, for the award of degree of DOCTOR OF PHILOSOPHY in the FACULTY OF PHARMACY was carried out by Mr. A. MADESWARAN, in College of Pharmacy, Sri Ramakrishna Institute of Paramedical Sciences, Coimbatore, under my direct supervision and guidance to my fullest satisfaction. The contents of this thesis, in full or in parts, have not been submitted to any other Institute or University for the award of any degree or diploma. Dr. K. Asok Kumar, M.Pharm., Ph.D. Professor & Head, Department of Pharmacology, College of Pharmacy, Sri Ramakrishna Institute of Paramedical Sciences, Coimbatore, Tamil Nadu - 641 044. Place: Coimbatore – 44. Date: Certificate This is to certify that the Ph.D. dissertation entitled “IN SILICO, IN VITRO AND IN VIVO MEMORY ENHANCING ACTIVITY OF CERTAIN COMMERCIALLY AVAILABLE FLAVONOIDS IN SCOPOLAMINE AND ALUMINIUM- INDUCED LEARNING IMPAIRMENT IN MICE” being submitted to The Tamil Nadu Dr.
  • Harmonized Tariff Schedule of the United States (2004) -- Supplement 1 Annotated for Statistical Reporting Purposes

    Harmonized Tariff Schedule of the United States (2004) -- Supplement 1 Annotated for Statistical Reporting Purposes

    Harmonized Tariff Schedule of the United States (2004) -- Supplement 1 Annotated for Statistical Reporting Purposes PHARMACEUTICAL APPENDIX TO THE HARMONIZED TARIFF SCHEDULE Harmonized Tariff Schedule of the United States (2004) -- Supplement 1 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. Product CAS No. Product CAS No. ABACAVIR 136470-78-5 ACEXAMIC ACID 57-08-9 ABAFUNGIN 129639-79-8 ACICLOVIR 59277-89-3 ABAMECTIN 65195-55-3 ACIFRAN 72420-38-3 ABANOQUIL 90402-40-7 ACIPIMOX 51037-30-0 ABARELIX 183552-38-7 ACITAZANOLAST 114607-46-4 ABCIXIMAB 143653-53-6 ACITEMATE 101197-99-3 ABECARNIL 111841-85-1 ACITRETIN 55079-83-9 ABIRATERONE 154229-19-3 ACIVICIN 42228-92-2 ABITESARTAN 137882-98-5 ACLANTATE 39633-62-0 ABLUKAST 96566-25-5 ACLARUBICIN 57576-44-0 ABUNIDAZOLE 91017-58-2 ACLATONIUM NAPADISILATE 55077-30-0 ACADESINE 2627-69-2 ACODAZOLE 79152-85-5 ACAMPROSATE 77337-76-9 ACONIAZIDE 13410-86-1 ACAPRAZINE 55485-20-6 ACOXATRINE 748-44-7 ACARBOSE 56180-94-0 ACREOZAST 123548-56-1 ACEBROCHOL 514-50-1 ACRIDOREX 47487-22-9 ACEBURIC ACID 26976-72-7
  • Marrakesh Agreement Establishing the World Trade Organization

    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
  • Identification of Phenolic Compounds from Peanut Skin Using HPLC-Msn

    Identification of Phenolic Compounds from Peanut Skin Using HPLC-Msn

    Identification of Phenolic Compounds from Peanut Skin using HPLC-MSn By Kyle A. Reed Dissertation submitted to the Faculty of the Virginia Polytechnic Institute and State University in partial fulfillment of the requirements for the degree of Doctor of Philosophy In Food Science and Technology Committee: Sean O’Keefe (Committee Chair) Rebecca O’Malley (Committee Co-Chair) Susan Duncan Kumar Mallikarjunan Joseph Marcy December 7, 2009 Blacksburg, Virginia Keywords: peanut skin, oligomeric proanthocyanidins, polyphenol, HPLC-MSn Identification of Phenolic Compounds from Peanut Skin using HPLC-MSn By Kyle A. Reed ABSTRACT Consumers view natural antioxidants as a safe means to reduce spoilage in foods. In addition, these compounds have been reported to be responsible for human health benefits. Identification of these compounds in peanut skins may enhance consumer interest, improve sales, and increase the value of peanuts. This study evaluated analytical methods which have not been previously incorporated for the analysis of peanut skins. Toyopearl size-exclusion chromatography (SEC) was used for separating phenolic size-classes in raw methanolic extract from skins of Gregory peanuts. This allowed for an enhanced analysis of phenolic content and antioxidant activity based on compound classes, and provided a viable preparatory separation technique for further identification. Toyopearl SEC of raw methanolic peanut skin extract produced nine fractions based on molecular size. Analysis of total phenolics in these fractions indicated Gregory peanut skins contain high concentrations of phenolic compounds. Further studies revealed the fractions contained compounds which exhibited antioxidant activities that were significantly higher than that of butylated hydroxyanisole (BHA), a common synthetic antioxidant used in the food industry.