DOCSLIB.ORG

United States Patent (19) [11] 3,843,788 Iwasa Et Al

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
United States Patent (19) [11] 3,843,788 Iwasa Et Al United States Patent (19) [11] 3,843,788 Iwasa et al. (45 Oct. 22, 1974 54 ANTI-PEPTIC ULCER SUBSTANCE FROM CORYDALISTUBERS (521 U.S. C. ................................................ 424/195 75 Inventors: Junzo Iwasa, Kyoto; Shunsuke 51 int. Cl............................................. A6 k 27/14 Naruto: Noboru Ikeda, both of 58. Field of Search..................................... 424/195 Osaka, Keiji Nakamura, Amagasaki; Yukinobu Sohji, Neyagawa, all of 56 References Cited Japan OTHER PUBLICATIONS 73 Assignee: Dainippon Pharmaceutical Co., Ltd., Evers, “The Chemistry of Drugs," pp. 124-127, Lon Osaka, Japan don: Ernest Benn Limited, (1926), Merck's 1907 Index, (3rd Ed.), p. 159, published by 22 Filed: Oct. 5, 1972 Merck & Co. N.Y. 21 Appl. No.: 295,163 Primary Examiner-Sam Rosen Related U.S. Application Data Attorney, Agent, or Firm-Clelle W. Upchurch 63 Continuation of Ser, No. 62,632, Aug. 10, 1970, abandoned, which is a continuation-in-part of Ser. 57) ABSTRACT No. 735,162, June 7, 1968, abandoned, which is a continuation-in-part of Ser. No. 649, 103, June 27, A method of treating peptic ulcers by oral administra 1967, abandoned, which is a continuation-in-part of tion of an active substance from Corydalis tubers, Ser. No. 493,267, Oct. 5, 1965, abandoned. preferably Corydalis bulbosa D.C., or dehydroco rydaline, compositions therefor and processes for the 30 Foreign Application Priority Data preparation thereof. - Oct. 20, 1964 Japan.............................. 39-0.596.33 2 Claims, No Drawings 3,843,788 2 ANT-PEPTIC ULCER SUBSTANCE FROM Another object of the present invention is to provide CORYDALISTUBERS therapeutic compositions, suitable for the aforesaid method of treatment. RELATION TO OTHERAPPLICATIONS Another object of the present invention is to provide This is a continuation of application Ser. No. 62,632, 5 a process for the formulation of the aforesaid therapeu filed Aug. 10, 1970 which is a continuation-in-part of tic composition. application Ser. No. 735,162, filed on June 7, 1968 A further object of the present invention is to provide which is, in turn, a continuation-in-part of application a substance containing anti-peptic ulcer active princi Ser. No. 649,103, filed on June 27, 1967 which is, in ples from the aforesaid tube of Corydalis genus. turn, a continuation-in-part of application Ser. No. 10 A still further object is to provide processes for the 493,267, filed on Oct. 5, 1965 all now abandoned. preparation of the aforesaid active substance and dehy drocorydaline. BRIEF SUMMARY OF THE INVENTION According to the present invention, it has been found This invention relates to a new therapeutic method that the substance from the tuber of Corydalis genus for the treatment of peptic ulcers and new pharmaceu 15 and dehydrocorydaline produced a strong anti-ulcer tical compositions therefor and methods for the prepa activity which was clinically proved later. Furthermore, ration thereof. no remarkable side effect, generally induced by choli More particularly, it relates to a method for the treat nolytic drugs, was encountered. ment of peptic ulcers by administering an active sub Although the principal ingredient of the said strong stance from the tuber of Corydalis genus or dehydroco action is believed to be dehydrocorydaline, the active rydaline, also to pharmaceutical compositions suitable substance of the invention apparently contains also ter for such treatment and processes for the preparation of tiary bases such as tetrahydropalmatine, protopine and the said active substance and dehydrocorydaline. the like, which enhance the anti-ulcer activity. The Some kinds of the tuber of Corydalis genus have been 25 present active substance from Corydalis tubers and de called “Yanhusuo' in China, Engosaku" in Japan and hydrocorydaline possess superior anti-ulcer activity "Corydalis tuber' in Europe. They have been used as without any anti-cholinergic activity. The mechanism an important medicament as analgesic and anti of the activity may be due to a sympathetic action. The spasmodic in Chinese Medicine and in Homeopathic activity was experimentally confirmed by suppression therapeutics. Also it was a home remedy in folk medi 30 of gastric secretion, excretion of pepsin and augmented cine in various parts of the world. However, heretofore intestinal motility. no one has discovered that a substance extracted from the tuber of Corydalis genus and dehydrocorydaline DETAILED DESCRIPTION OF THE INVENTION which is a main active component of the said substance The active substance of the invention is obtained by are particularly useful in the treatment of gastric ulcers. 35 the following procedure. A tuber of Corydalis genus is repeatedly extracted with a solvent including water, a The present invention results from a study of the lower alcohol such as methanol, ethanol and propanol, tuber of Corydalis genus. It has now been discovered or mixtures thereof. The combined extract is concen that the tuber of Corydalis genus includes an anti 40 trated by evaporation under reduced pressure and the peptic ulcer active substance, and then the processes of concentrated extract is acidified to a pH value between preparing this product at low cost have been discov 1 and 4 by addition of dilute organic or mineral acid, ered too. such as acetic, tartaric, citric, hydrochloric, hydro The tuber of Corydalis genus of the present invention bromic or sulphuric acid. The fat present in the aque is a tuber of a plant belonging to the genus Corydalis, 45 ous solution is removed by extracting with a hydrocar including Corydalis bulbosa D.C., Corydalis bulbosa bon solvent such as the so-called petroleum ether or D.C. var. typica Regel, Corydalis ambigua Cham, et petroleum benzin. The defatted acidic layer is made al Schlecht., Corydalis aurea Will., Corydalis Nakai kaline to a pH value between 7.5 and 12, preferably be Ishidoya, Corydalis decunbens Pers., Corydalis remota tween 9 and 10, with ammonia, alkali metal hydroxide Fisch. var. genuina Maxim., Corydalis ambigua Cham. 50 such as sodium hydroxide and potassium hydroxide, al et Schlecht. var.amurensis Maxim. and Corydalis tuber kali metal carbonate such as sodium carbonate and po osa D.C. Among these varieties, Corydalis bulbosa D.C., tassium carbonate or alkali metal bicarbonate such as Corydalis ambigua Cham. et Schlecht., Corydalis am sodium bicarbonate and potassium bicarbonate. The bigua Cham. et Schlecht, var. amurensis Maxim. and resulting precipitate is filtered off from the defatted al Corydalis tuberosa D.C., more particularly, Corydalis 55 kaline solution and the filtrate is extracted with a halo bulbosa D.C. and Corydalis ambigua Cham. et Schlecht. genated hydrocarbon such as chloroform, dichloro are preferred. These tubers contain a large amount of methane, trichloroethane and carbon tetrachloride. alkaloid, more particularly dehydrocorydaline. Being separated from the mixture and then being pref Corydalis bulbosa D.C. and Corydalis ambigua Cham. erably acidified or neutralized with alcoholic hydrogen et Schlecht. are called "Chinese Corydalis.' The com 60 chloride, the halogenated hydrocarbon layer is evapo mercial article, however, may include tubers of other rated to dryness under reduced pressure to give an ac varieties. tive fraction A. One object of the present invention is to provide the The active substance may be also prepared by direct medical profession with an improved method of treat extraction from the defatted alkaline solution with the ing peptic ulcers by the administration of an active 65 halogenated hydrocarbon above-mentioned without therapeutic substance extracted from Corydalis tubers filtration step. The active fraction obtained in this way and dehydrocorydaline. is designated fraction B. 3,843,788 3 Each of the fractions A and B thus obtained possesses strong anti-ulcer properties and is valuable for clinical CHO use, as shown below. The dehydrocorydaline used in the present invention CIG N/NS-- z may be in a form of its salts such as mineral acid salts, Fifth step e.g., chloride, bromide, iodide, nitrate or sulphate or --d organic acid salts, e.g., tannate, glycyrrhizate, anisate, CI gallate, benzilate, D-glucuronate or citrate having the following formula: --OC, O N/ CHO (vii) CHO N: A CII, O- r 5 CIO N/N CH3 O CH f CIICOCl, sixth step CH -OCH3 -OCH (I) 20 -OCH3 wherein A is an anion. This compound may be prepared by extracting from (VIII) tubers of Corydalis genus, but may be more commer cially prepared by a synthetic method, i.e., by the fol lowing procedure. 25 CHO ?^ CIO - C s First steps 30 N -OCII -O CH (I) 35 In the above scheme, X is a halogen atom, Y is a hal ogen atom or sulphate anion, Z is a halogen atom, Sul phate anion or methylsulphate anion, R and R2 are each hydrogen atom or methyl group and A is the same 40 as defined above. CH3COCH3 second step In the first step, berberine halide (II) is reacted with acetone in the presence of alkali such as sodium hy -CO, droxide, potassium hydroxide, sodium methoxide, so OCH dium ethoxide, potassium methoxide or potassium 45 ethoxide to give 8-acetonylberberine (III). -OCH The resulting 8-acetonylberberine (III) is reacted with a methyl halide, e.g., methyl chloride, methyl bro mide or methyl iodide to give 13-methylberberine hal ide (IV) in the second step. The reaction may be car 50 ried out by heating at approximately 80 - 120°C. for several minutes to several hours, preferably 30 minutes to 3 hours in an autoclave or in a sealed tube. Although the obtained 13-methylberberine halide (IV) is in a -OCH3 state of admixture with berberine halide (V), it can be 55 readily purified by utilizing their difference of solubility -OCH3 into organic solvents, that is, 13-methylberberine hal ide (IV) can be separated from the mixture by extract (IV) V) ing with an organic solvent such as dichloromethane or chloroform.
Load more

Recommended publications
  • Review Article SOME PLANTS AS a SOURCE of ACETYL CHOLINESTERASE INHIBITORS: a REVIEW Purabi Deka *, Arun Kumar, Bipin Kumar Nayak, N
    Purabi Deka et al. Int. Res. J. Pharm. 2017, 8 (5) INTERNATIONAL RESEARCH JOURNAL OF PHARMACY www.irjponline.com ISSN 2230 – 8407 Review Article SOME PLANTS AS A SOURCE OF ACETYL CHOLINESTERASE INHIBITORS: A REVIEW Purabi Deka *, Arun Kumar, Bipin Kumar Nayak, N. Eloziia Division of Pharmaceutical Sciences, Shri Guru Ram Rai Institute of Technology & Science, Dehradun, India *Corresponding Author Email: [email protected] Article Received on: 27/03/17 Approved for publication: 27/04/17 DOI: 10.7897/2230-8407.08565 ABSTRACT The term dementia derives from the Latin demens (“de” means private, “mens” means mind, intelligence and judgment- “without a mind”). Dementia is a progressive, chronic neurological disorder which destroys brain cells and causes difficulties with memory, behaviour, thinking, calculation, comprehension, language and it is brutal enough to affect work, lifelong hobbies, and social life. Alzheimer’s disease, Parkinson’s disease, Dementia with Lewys Bodies are some common types of dementias. Acetylcholinesterase AChE) Inhibition, the key enzyme which plays a main role in the breakdown of acetylcholine and it is considered as a Positive strategy for the treatment of neurological disorders. Currently many AChE inhibitors namely tacrine, donepezil, rivastigmine, galantamine have been used as first line drug for the treatment of Alzheimer’s disease. They are having several side effects such as gastrointestinal disorder, hepatotoxicity etc, so there is great interest in finding new and better AChE inhibitors from Natural products. Natural products are the remarkable source of Synthetic as well as traditional products. Abundance of plants in nature gives a potential source of AChE inhibitors. The purpose of this article to present a complete literature survey of plants that have been tested for AChE inhibitory activity.
    [Show full text]
  • Pdate Roduct
    Environmental Analysis Analytical Chemistry Standard 2002 No.3 Dioxin Endocrine Air Pollutant Water Solvents Chromatography Indicator JCSS Wetting Ultratrace Supramolecular Spectrochemical pdate U :20:32 roduct P ako W WakoPureChemical KYOSHINSHA Title:ProUpNo3/表紙訂正分 Page:1 Date: 2003/06/06 Fri 17 KYOSHINSHA Title:ProUpNo3/表紙訂正分 Page:2 Date: 2003/06/06 Fri 17:20:34 Index ENVIRONMENTAL ANALYSIS • Wakopak® Fluofix 1. Dioxins Analysis • Wakopak® Combi CN A. Multilayer Silica Gel Column Chromatography ................... 1 • Wakogel DX (Silica Gel) (238-01781) B. Reagents for Ion Pair Chromatography (IPC) ...................... 9 • Sodium Sulfate (194-12221) • Tetra-n -butylammonium Phosphate Soln. (207-13701) • Decane (048-28543, 042-28541) • 1-Pentanesulfonic Acid Sodium Salt Soln. (169-18231) • Ethanol (99.5) (056-06663, 050-06661) • 1-Hexanesulfonic Acid Sodiom Salt Soln. (086-07141) • Nonane (148-07351, 142-07354) • 1-Heptanesulfonic Acid Sodium Salt Soln. (083-07151) • Petroleum ether (160-20231) • 1-Octanesulfonic Acid Sodium Salt Soln. (155-01941) B. Dioxin Trap Beads ...................................................... 2 • Dioxin Trap Beads (040-27481) 2. Indicators-100 mL brown-glass dropper bottle- C. Active Carbon-impregnated Silica Gel ............................. 2 for titration & pH Measurement ................................. 10 • Activated Carbon-impregnated Silica Gel (019-11941) 3. JCSS Standards ....................................................... 11 2. Endocrine Analysis A. Reagent Kits ............................................................
    [Show full text]
  • Download Download
    International Journal of Biotechnology for Wellness Industries, 2016, 5, 91-110 91 Bioactive Natural Products from Plants and Biotechnological Approaches for their Production Niraj Tripathi, Swapnil Sapre, Iti Gontia-Mishra, Vijay Prakash and Sharad Tiwari* Biotechnology Centre, Jawaharlal Nehru Agricultural University, Jabalpur 482004, India Abstract: Bioactive natural products are economically important as drugs, fragrances, pigments, food additives and pesticides. The biotechnological tools are important to select, multiply, improve and analyze medicinal plants for production of such products. The utilization of medicinal plant cells for the production of natural or recombinant compounds of commercial interest has gained increasing attention over the past decades. Plant tissue culture systems are possible source of valuable medicinal compounds, fragrances and colorants, which cannot be produced by microbial cells or chemical synthesis. In vitro production of bioactive natural products in plant cell suspension culture has been reported from various medicinal plants and bioreactors are the key step towards commercial production. Genetic transformation is a powerful tool for enhancing the productivity of novel products; especially by Agrobacterium tumefacians. Combinatorial biosynthesis is another approach in the generation of novel natural products and for the production of rare and expensive natural products. Recent advances in the molecular biology, enzymology and bioreactor technology of plant cell culture suggest that these systems may become a viable source of important secondary metabolites. Genetic fingerprinting could be a powerful tool in the field of medicinal plants to be used for correct germplasm identification. In addition, when linked to emerging tools such as metabolomics and proteomics, providing fingerprints of the plant’s metabolites or protein composition, it gives data on phenotypic variation, caused by growth conditions or environmental factors, and also yield data on the genes involved in the biosynthesis.
    [Show full text]
  • Drug Metabolism, Pharmacokinetics and Bioanalysis
    Drug Metabolism, Pharmacokinetics and Bioanalysis Edited by Hye Suk Lee and Kwang-Hyeon Liu Printed Edition of the Special Issue Published in Pharmaceutics www.mdpi.com/journal/pharmaceutics Drug Metabolism, Pharmacokinetics and Bioanalysis Drug Metabolism, Pharmacokinetics and Bioanalysis Special Issue Editors Hye Suk Lee Kwang-Hyeon Liu MDPI • Basel • Beijing • Wuhan • Barcelona • Belgrade Special Issue Editors Hye Suk Lee Kwang-Hyeon Liu The Catholic University of Korea Kyungpook National University Korea Korea Editorial Office MDPI St. Alban-Anlage 66 4052 Basel, Switzerland This is a reprint of articles from the Special Issue published online in the open access journal Pharmaceutics (ISSN 1999-4923) in 2018 (available at: https://www.mdpi.com/journal/ pharmaceutics/special issues/dmpk and bioanalysis) For citation purposes, cite each article independently as indicated on the article page online and as indicated below: LastName, A.A.; LastName, B.B.; LastName, C.C. Article Title. Journal Name Year, Article Number, Page Range. ISBN 978-3-03897-916-6 (Pbk) ISBN 978-3-03897-917-3 (PDF) c 2019 by the authors. Articles in this book are Open Access and distributed under the Creative Commons Attribution (CC BY) license, which allows users to download, copy and build upon published articles, as long as the author and publisher are properly credited, which ensures maximum dissemination and a wider impact of our publications. The book as a whole is distributed by MDPI under the terms and conditions of the Creative Commons license CC BY-NC-ND. Contents About the Special Issue Editors ..................................... vii Preface to ”Drug Metabolism, Pharmacokinetics and Bioanalysis” ................. ix Fakhrossadat Emami, Alireza Vatanara, Eun Ji Park and Dong Hee Na Drying Technologies for the Stability and Bioavailability of Biopharmaceuticals Reprinted from: Pharmaceutics 2018, 10, 131, doi:10.3390/pharmaceutics10030131 ........
    [Show full text]
  • Acetylcholinesterase
    AChE Acetylcholinesterase Acetylcholinesterase (AChE or acetylhydrolase) is a hydrolase that hydrolyzes the neurotransmitter acetylcholine. AChE is found at mainly neuromuscular junctions and cholinergic brain synapses, where its activity serves to terminate synaptic transmission. It belongs tocarboxylesterase family of enzymes. It is the primary target of inhibition by organophosphorus compounds such as nerve agents and pesticides. AChE has a very high catalytic activity - each molecule of AChE degrades about 25000 molecules ofacetylcholine (ACh) per second, approaching the limit allowed by diffusion of the substrate. ACh is released from the nerve into the synaptic cleft and binds to ACh receptors on the post-synaptic membrane, relaying the signal from the nerve. AChE, also located on the post-synaptic membrane, terminates the signal transmission by hydrolyzing ACh. The liberated choline is taken up again by the pre-synaptic nerve and ACh is synthetized by combining with acetyl-CoA through the action of choline acetyltransferase. www.MedChemExpress.com 1 AChE Inhibitors & Activators (+)-Phenserine (-)-Corynoxidine Cat. No.: HY-16009 Cat. No.: HY-N7010 (+)-Phenserine is a novel selective cholinesterase (-)-Corynoxidine is an acetylcholinesterase noncompetitive inhibitor with an IC50 of 45.3 μM. inhibitor with an IC50 value of 89.0 μM, isolated from the aerial parts of Corydalis speciosa. (-)-Corynoxidine exhibits antibacterial activities against Staphylococcus aureus and methicillin-resistant S. Purity: 98.09% Purity: >98% Clinical Data: No Development Reported Clinical Data: No Development Reported Size: 5 mg, 10 mg, 50 mg Size: 1 mg, 5 mg (-)-Huperzine A (R)-Rivastigmine D6 tartrate (Huperzine A) Cat. No.: HY-17387 Cat. No.: HY-11017AS (-)-Huperzine A (Huperzine A) is an alkaloid (R)-Rivastigmine D6 tartrate is the deuterium isolated from a Chinese club moss, with labeled (R)-Rivastigmine, which is an neuroprotective activity.
    [Show full text]
  • Toxins and Signalling Evelyne Benoit, Françoise Goudey-Perriere, P
    Toxins and Signalling Evelyne Benoit, Françoise Goudey-Perriere, P. Marchot, Denis Servent To cite this version: Evelyne Benoit, Françoise Goudey-Perriere, P. Marchot, Denis Servent. Toxins and Signalling. SFET Publications, Châtenay-Malabry, France, pp.204, 2009. hal-00738643 HAL Id: hal-00738643 https://hal.archives-ouvertes.fr/hal-00738643 Submitted on 21 May 2020 HAL is a multi-disciplinary open access L’archive ouverte pluridisciplinaire HAL, est archive for the deposit and dissemination of sci- destinée au dépôt et à la diffusion de documents entific research documents, whether they are pub- scientifiques de niveau recherche, publiés ou non, lished or not. The documents may come from émanant des établissements d’enseignement et de teaching and research institutions in France or recherche français ou étrangers, des laboratoires abroad, or from public or private research centers. publics ou privés. Collection Rencontres en Toxinologie © E. JOVER et al. TTooxxiinneess eett SSiiggnnaalliissaattiioonn -- TTooxxiinnss aanndd SSiiggnnaalllliinngg © B.J. LAVENTIE et al. Comité d’édition – Editorial committee : Evelyne BENOIT, Françoise GOUDEY-PERRIERE, Pascale MARCHOT, Denis SERVENT Société Française pour l'Etude des Toxines French Society of Toxinology Illustrations de couverture – Cover pictures : En haut – Top : Les effets intracellulaires multiples des toxines botuliques et de la toxine tétanique - The multiple intracellular effects of the BoNTs and TeNT. (Copyright Emmanuel JOVER, Fréderic DOUSSAU, Etienne LONCHAMP, Laetitia WIOLAND, Jean-Luc DUPONT, Jordi MOLGÓ, Michel POPOFF, Bernard POULAIN) En bas - Bottom : Structure tridimensionnelle de l’alpha-toxine staphylocoque - Tridimensional structure of staphylococcal alpha-toxin. (Copyright Benoit-Joseph LAVENTIE, Daniel KELLER, Emmanuel JOVER, Gilles PREVOST) Collection Rencontres en Toxinologie La collection « Rencontres en Toxinologie » est publiée à l’occasion des Colloques annuels « Rencontres en Toxinologie » organisés par la Société Française pour l’Etude des Toxines (SFET).
    [Show full text]
  • Dr. Duke's Phytochemical and Ethnobotanical Databases List of Chemicals for Tinnitus
    Dr. Duke's Phytochemical and Ethnobotanical Databases List of Chemicals for Tinnitus Chemical Activity Count (+)-ALPHA-VINIFERIN 1 (+)-AROMOLINE 1 (+)-BORNYL-ISOVALERATE 1 (+)-CATECHIN 1 (+)-EUDESMA-4(14),7(11)-DIENE-3-ONE 1 (+)-HERNANDEZINE 2 (+)-ISOLARICIRESINOL 1 (+)-NORTRACHELOGENIN 1 (+)-PSEUDOEPHEDRINE 1 (+)-SYRINGARESINOL-DI-O-BETA-D-GLUCOSIDE 1 (+)-T-CADINOL 1 (-)-16,17-DIHYDROXY-16BETA-KAURAN-19-OIC 1 (-)-ALPHA-BISABOLOL 1 (-)-ANABASINE 1 (-)-APOGLAZIOVINE 1 (-)-BETONICINE 1 (-)-BORNYL-CAFFEATE 1 (-)-BORNYL-FERULATE 1 (-)-BORNYL-P-COUMARATE 1 (-)-CANADINE 1 (-)-DICENTRINE 1 (-)-EPICATECHIN 2 (-)-EPIGALLOCATECHIN-GALLATE 1 (1'S)-1'-ACETOXYCHAVICOL-ACETATE 1 (E)-4-(3',4'-DIMETHOXYPHENYL)-BUT-3-EN-OL 1 1,7-BIS-(4-HYDROXYPHENYL)-1,4,6-HEPTATRIEN-3-ONE 1 1,8-CINEOLE 4 Chemical Activity Count 1-ETHYL-BETA-CARBOLINE 2 10-ACETOXY-8-HYDROXY-9-ISOBUTYLOXY-6-METHOXYTHYMOL 1 10-DEHYDROGINGERDIONE 1 10-GINGERDIONE 1 12-(4'-METHOXYPHENYL)-DAURICINE 1 12-METHOXYDIHYDROCOSTULONIDE 1 13',II8-BIAPIGENIN 1 13-HYDROXYLUPANINE 1 13-OXYINGENOL-ESTER 1 16,17-DIHYDROXY-16BETA-KAURAN-19-OIC 1 16-HYDROXY-4,4,10,13-TETRAMETHYL-17-(4-METHYL-PENTYL)-HEXADECAHYDRO- 1 CYCLOPENTA[A]PHENANTHREN-3-ONE 16-HYDROXYINGENOL-ESTER 1 2'-O-GLYCOSYLVITEXIN 1 2-BETA,3BETA-27-TRIHYDROXYOLEAN-12-ENE-23,28-DICARBOXYLIC-ACID 1 2-METHYLBUT-3-ENE-2-OL 2 2-VINYL-4H-1,3-DITHIIN 1 20-DEOXYINGENOL-ESTER 1 22BETA-ESCIN 1 24-METHYLENE-CYCLOARTANOL 2 3,3'-DIMETHYLELLAGIC-ACID 1 3,4-DIMETHOXYTOLUENE 2 3,4-METHYLENE-DIOXYCINNAMIC-ACID-BORNYL-ESTER 1 3,4-SECOTRITERPENE-ACID-20-EPI-KOETJAPIC-ACID
    [Show full text]
  • WO 2010/075469 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 1 July 2010 (01.07.2010) WO 2010/075469 Al (51) International Patent Classification: (74) Agent: MEARA, Joseph, P.; Foley & Lardner LLP, 150 C07D 455/03 (2006.01) A61K 31/4741 (2006.01) East Gilman Street, Post Office Box 1497, Madison, WI C07D 495/04 (2006.01) A61P 3/06 (2006.01) 53701 (US). (21) International Application Number: (81) Designated States (unless otherwise indicated, for every PCT/US2009/06933 1 kind of national protection available): AE, AG, AL, AM, AO, AT, AU, AZ, BA, BB, BG, BH, BR, BW, BY, BZ, (22) International Filing Date: CA, CH, CL, CN, CO, CR, CU, CZ, DE, DK, DM, DO, 22 December 2009 (22.12.2009) DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, (25) Filing Language: English HN, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KN, KP, KR, KZ, LA, LC, LK, LR, LS, LT, LU, LY, MA, MD, (26) Publication Language: English ME, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, (30) Priority Data: NO, NZ, OM, PE, PG, PH, PL, PT, RO, RS, RU, SC, SD, 61/140,551 23 December 2008 (23.12.2008) US SE, SG, SK, SL, SM, ST, SV, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW. (71) Applicant (for all designated States except US): CVI PHARMACEUTICALS LIMITED [GB/GB]; Scotia (84) Designated States (unless otherwise indicated, for every Centre, 4th Floor, P.O.
    [Show full text]
  • Pharmacological Action of DA-9701 on the Motility of Feline Stomach Circular Smooth Muscle
    ORIGINAL ARTICLES Department of Pharmacology1, College of Pharmacy, Chung-Ang University, Seoul; Department of Oriental Medical Food & Nutrition2, Semyung University, Jecheon-si Republic of Korea Pharmacological action of DA-9701 on the motility of feline stomach circular smooth muscle Thanh Thao Nguyen 1, Hyun Ju Song 1, Sung Kwon Ko 2, Uy Dong Sohn 1 Received February 20, 2014, accepted March 22, 2014 Prof. Uy Dong Sohn, Department of Pharmacology, College of Pharmacy, Chung-Ang University, 84 Heuseok-Ro, Dongjak-gu, Seoul 156-756, Republic of Korea. [email protected] Pharmazie 70: 183–192 (2015) doi: 10.1691/ph.2015.4563 DA-9701, a new prokinetic agent for the treatment of functional dyspepsia, is formulated with Pharbitis semen and Corydalis tuber. This study wasconducted to determine the pharmacological action of DA-9701 and to identify the receptorsinvolved in DA-9701-induced contractile responsesin the feline gastric corporal, fundic and antral circular smooth muscle. Concentration-response curve to DA-9701 was established. The tissue trips were exposed to methylsergide, ketanserin, ondansetron, GR 113808, atropine and dopamine before administration ofDA-9701. The contractile force was determined before and after administration of drugs by a polygraph.DA-9701 enhanced the spontaneous contractile amplitude of antrum, corpus and fundus. However, it did not change the spontaneous contractile frequency of antrum and corpus, but concentration-dependently reduced that of fundus. In the fundus, DA-9701-induced tonic contractions were inhibited by dopamine, methylsergide, ketanserine, ondansetron or GR 113808 respectively, but not by atropine, indicating that the contractile responses are mediated by multiple receptors: 5-HT2, 5-HT3, 5-HT4, and dopamine receptors.
    [Show full text]
  • Introduction (Pdf)
    Dictionary of Natural Products on CD-ROM This introduction screen gives access to (a) a general introduction to the scope and content of DNP on CD-ROM, followed by (b) an extensive review of the different types of natural product and the way in which they are organised and categorised in DNP. You may access the section of your choice by clicking on the appropriate line below, or you may scroll through the text forwards or backwards from any point. Introduction to the DNP database page 3 Data presentation and organisation 3 Derivatives and variants 3 Chemical names and synonyms 4 CAS Registry Numbers 6 Diagrams 7 Stereochemical conventions 7 Molecular formula and molecular weight 8 Source 9 Importance/use 9 Type of Compound 9 Physical Data 9 Hazard and toxicity information 10 Bibliographic References 11 Journal abbreviations 12 Entry under review 12 Description of Natural Product Structures 13 Aliphatic natural products 15 Semiochemicals 15 Lipids 22 Polyketides 29 Carbohydrates 35 Oxygen heterocycles 44 Simple aromatic natural products 45 Benzofuranoids 48 Benzopyranoids 49 1 Flavonoids page 51 Tannins 60 Lignans 64 Polycyclic aromatic natural products 68 Terpenoids 72 Monoterpenoids 73 Sesquiterpenoids 77 Diterpenoids 101 Sesterterpenoids 118 Triterpenoids 121 Tetraterpenoids 131 Miscellaneous terpenoids 133 Meroterpenoids 133 Steroids 135 The sterols 140 Aminoacids and peptides 148 Aminoacids 148 Peptides 150 β-Lactams 151 Glycopeptides 153 Alkaloids 154 Alkaloids derived from ornithine 154 Alkaloids derived from lysine 156 Alkaloids
    [Show full text]
  • Recent Progress on Biological Activity of Amaryllidaceae and Further Isoquinoline Alkaloids in Connection with Alzheimer’S Disease
    molecules Review Recent Progress on Biological Activity of Amaryllidaceae and Further Isoquinoline Alkaloids in Connection with Alzheimer’s Disease Lucie Cahlíková 1,* , Rudolf Vrabec 2, Filip Pidaný 1, Rozálie Peˇrinová 1, Negar Maafi 1 , Abdullah Al Mamun 1 , Aneta Ritomská 1, Viriyanata Wijaya 1 and Gerald Blunden 3 1 ADINACO Research Group, Department of Pharmaceutical Botany, Faculty of Pharmacy, Charles University, Heyrovskeho 1203, 500 05 Hradec Kralove, Czech Republic; [email protected] (F.P.); [email protected] (R.P.); [email protected] (N.M.); [email protected] (A.A.M.); [email protected] (A.R.); [email protected] (V.W.) 2 Department of Pharmacognosy, Faculty of Pharmacy, Charles University, Heyrovskeho 1203, 500 05 Hradec Kralove, Czech Republic; [email protected] 3 School of Pharmacy and Biomedical Sciences, University of Portsmouth, Portsmouth, Hampshire P01 2DT, UK; [email protected] * Correspondence: [email protected]; Tel.: +420-495-067-311 Abstract: Alzheimer’s disease (AD) is a progressive age-related neurodegenerative disease recog- nized as the most common form of dementia among elderly people. Due to the fact that the exact pathogenesis of AD still remains to be fully elucidated, the treatment is only symptomatic and available drugs are not able to modify AD progression. Considering the increase in life expectancy worldwide, AD rates are predicted to increase enormously, and thus the search for new AD drugs is Citation: Cahlíková, L.; Vrabec, R.; urgently needed. Due to their complex nitrogen-containing structures, alkaloids are considered to be Pidaný, F.; Peˇrinová,R.; Maafi, N.; promising candidates for use in the treatment of AD.
    [Show full text]
  • Aldrich FT-IR Collection Edition II
    Aldrich FT-IR Collection Edition II Library Listing – 18,454 spectra This library represents the most comprehensive collection of FT-IR spectral references available. It contains the most common chemicals found in the Aldrich Handbook of Fine Chemicals. The Aldrich Collection of FT-IR Spectra Edition II library contains spectra of 18,454 pure compounds and comes with the Second Edition of the Aldrich Library of FT-IR Spectra (a 3-volume book set). All spectra were acquired by Sigma-Aldrich Co. and were processed by Thermo Electron Corporation. Solid samples were run as mulls. Liquids were run neat. The following information is available when known: • Index number • Compound name • Molecular formula • Molecular weight • Boiling point • Melting point • Flash point • Density • Refractive index • Category name This library represents the largest collection of spectra collected entirely by FT-IR instrumentation. Eight smaller Aldrich Material Specific Sub-Libraries are also available. Aldrich FT-IR Collection Edition II Index Compound Name Index Compound Name 14261 4,4'-Diphenyl-2,2'-dipyridyl 16353 (+)-5alpha-Androstan-17beta-ol-3-one 5936 ((1R)-(endo,anti))-(+)-3- benzoate, 98% Bromocamphor-8- sulfonic acid, 5260 (+)-6-Aminopenicillanic acid, 96% ammonium salt 10157 (+)-6-Methoxy-alpha-methyl-2- 2683 ((1R)-endo)-(+)-3-Bromocamphor, 98% naphthaleneacetic acid, 98% 5937 ((1S)-(endo,anti))-(-)-3-Bromocamphor- 16306 (+)-Androsta-1,4-diene-3,17-dione, 98% 8- sulfonic acid, ammonium salt 1148 (+)-Arabinogalactan 2684 ((1S)-endo)-(-)-3-Bromocamphor,
    [Show full text]