DOCSLIB.ORG

Sulfonanilide Compounds

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
Sulfonanilide Compounds ~" ' Nil II II II Nil 1 1 Nil II MINI II J European Patent Office o «i -» © Publication number: 0 31/ 332 B1 Office europeen* des.. brevets , © EUROPEAN PATENT SPECIFICATION © Date of publication of patent specification: 19.05.93 © Int. CI.5: C07C 311/08, C07D 309/12, C07D 211/46, C07C 317/14, © Application number: 88310899.5 C07C 323/18, C07D 335/02, A61K 31/18, A61K 31/33 (5)nn, Date of filing: 18.11.88AOAAOO ' © Sulfonanilide compounds. ® Priority: 19.11.87 JP 292856/87 Urawa-shi(JP) Inventor: Ohuchi, Yutaka @ Date of publication of application: Azumaso 101, 12-11 Oyaba-2-chome 24.05.89 Bulletin 89/21 Urawa-shl(JP) Inventor: Sekluchl, Kazuto © Publication of the grant of the patent: 2716-4-1-204 Oaza Kawarabukl 19.05.93 Bulletin 93/20 Ageo-shl(JP) Inventor: Salto, Shlujl © Designated Contracting States: Pakusaldo Maehara 202 31-12, Torocho- AT BE CH DE FR GB IT LI LU NL SE 1 - chome Omlya-shl(JP) © References cited: Inventor: Hatayama, Katsuo EP-A- 0 093 591 Danchl 35-3 1200-215, Horlsaklcho FR- A- 2 244 473 Omlya- shl(JP) US- A- 3 725 451 Inventor: Sota, Kaoru US-A- 3840 597 1158- 11, Shlmotoml US- A- 3 856 859 Tokorozawa- shl(JP) © Proprietor: TAISHO PHARMACEUTICAL CO. LTD © Representative: Colelro, Raymond et al 00 24- 1 Takata 3- chome Toshlma- ku MEWBURN ELLIS & CO. 2/3 Cursltor Street CM Tokyo 1 71 (JP) London EC4A 1BQ (GB) CO CO @ Inventor: Yoshlkawa, Kensel IV 2878, Dalmon CO Note: Within nine months from the publication of the mention of the grant of the European patent, any person may give notice to the European Patent Office of opposition to the European patent granted. Notice of opposition shall be filed in a written reasoned statement. It shall not be deemed to have been filed until the opposition fee has been paid (Art. 99(1) European patent convention). Rank Xerox (UK) Business Services (3. 10/3.6/3.3. 1) EP 0 317 332 B1 Description The present invention relates to sulfonanilide compounds and more particularly sulfonanilide com - pounds and the pharmaceutical^ acceptable salts thereof having anti - inflammatory effect. 5 In U.S. Patents Nos. 3,840,597, 3,856,859 and 3,906,024 and Japanese Patent Kokai No. 10,584 (1986), there are disclosed sulfonamide compounds having substituted phenyl groups via an oxygen atom or a sulfur atom and showing anti - inflammatory effect [e.g., N-(4-nitro-2-phenoxy-phenyl)- methanesulfonamide]. However, there is a problem that drugs showing anti - inflammatory effect have gastrointestinal injuries io as clinical side effects. SUMMARY OF THE INVENTION As a result of the earnest research for the purpose of the above, the present inventors have found the 75 compounds showing anti - inflammatory, antipyretic and analgesic effects and further showing the decrease of side effects such as gastrointestinal injuries, and accomplished the present invention. According to the present invention, there is provided sulfonanilide compounds represented by the formula 20 NHS02R1 I R2 25 I N02 30 wherein R1 is a lower alkyl group or a trifluoromethyl group, R2 is a cycloalkylidenemethyl group, a group of the formula -A-R3 (wherein A is an oxygen atom, a sulfur atom, a sulfinyl group or a sulfonyl group and R3 is a cycloalkyl group having 5-8 carbon atoms; a cycloalkyl group having 5-8 carbon atoms 35 substituted by one or two of a lower alkyl group, an oxo group, a hydroxyl group or a methanesulfonyloxy group; a tetrahydropyranyl group; a tetrahydrothiopyranyl group; or a 1 - methylpiperidyl group) or a group of the formula - B - R+ (wherein B is a carbonyl group, a hydroxymethylene group or a methylene group, R+ is a cycloalkyl group having 5-8 carbon atoms) and the pharmaceutically acceptable salts thereof. 40 BRIEF DESCRIPTION OF THE DRAWING Figure 1 shows the body weight change in Experiment 2. DETAILED DESCRIPTION OF THE INVENTION 45 In the present invention, the cycloalkylidenemethyl group refers to a cyclopentylidenemethyl group, a cyclohexylidenemethyl group and the like. The lower alkyl group refers to a lower alkyl group having 1 to 4 carbon atoms such as, for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a tert- butyl group and the like, and the cycloalkyl group having 5-8 carbon atoms refers to 50 a cyclopentyl group, a cyclohexyl group, a cycloheptyl group and a cyclooctyl group. The pharmaceutically acceptable salt refers to inorganic salts such as a lithium salt, a sodium salt, a potassium salt, a calcium salt and the like, and salts with organic amines such as triethylamine, ethanolamine and the like. Among the preferred compounds of the present invention are compounds of Formula I wherein R1 is a 55 methyl group or a trifluoromethyl group, R2 is a cyclopentyloxy group, a cyclohexyloxy group, a cyclopen - tylthio group and a tetrahydro-4H-thiopyranyloxy group. The compounds of Formula I can be prepared, for example, from known compounds according to the following methods. 2 EP 0 317 332 B1 (1) A compound of Formula I wherein R2 is -A-R3 (wherein A is an oxygen atom or a sulfur atom) can be prepared from a 2 - halonitrobenzene as a starting material. Namely, a 2 - halonitrobenzene is reacted with a compound of the formula R3-YH (wherein R3 is as defined above, and Y is an oxygen atom or a sulfur atom) in the presence of a base and/or copper to 5 give a compound of the formula N02 I Y-R3 10 II 15 (wherein Y and R3 are as defined above). Examples of the base used in the reaction are alkali hydroxides such as sodium hydroxide, potassium hydroxide and the like, alkali hydrides such as sodium hydride, potassium hydride and the like, alkali carbonates such as sodium carbonate, potassium carbonate and the like, and alkoxides such as sodium ethoxide, potassium tert - butoxide and the like. 20 Next, the compound of Formula II is reduced to give an amino form. The reduction may be an ordinary reduction by which a nitro group is reduced to an amino group, for example, catalytic reduction using palladium or platinum, or reduction using iron, tin, sodium sulfide -ammonium chloride, sodium borohydride or lithium alminum hydride. Subsequently, the amino form obtained above is reacted with a compound of the formula R1S02X or 25 (R1S02)20 (wherein R1 is as defined above, and X is a fluorine atom, a chlorine atom, a bromine atom or an iodine atom) to give a sulfonanilide form, which is then nitrated to give a compound of the present invention represented by the formula NHSO2R1 I Y-R3 III 35 NO 2 40 wherein R1, R3 and Y are as defined above. (2) A compound of Formula I wherein R2 is - 0 - R3 can be also obtained from 2 - hydroxy - 4 - nitroaniline as a starting material. Namely, 2-hydroxy-4-nitroaniline is reacted with a compound of the formula R3-X (wherein R3 and X are as defined above ) in the presence of a base and followed by reacting with a compound of the formula R1S02X or (R1S02)20 (wherein R1 and X are as defined above 45 ) to give a compound of Formula I. (3) A compound of Formula I wherein R2 is -A-R3 (wherein A is as defined above, and R3 is a cycloalkyl group substituted by a hydroxyl group) can be prepared according to the following method. That is, this compound can be prepared by reducing the compound of Formula I wherein R3 is an oxocycloalkyl group, obtained in the method of item (1). The reduction used in this reaction may be an 50 ordinary reduction by which a ketone is converted to an alcohol, for example, a reduction using sodium borohydride, lithium alminum hydride, diborane, lithium, sodium and the like. (4) A compound of Formula I wherein R2 is -A-R3 (wherein A is as defined above, and R3 is an oxocycloalkyl group) can be also prepared according to the following method. More particularly, this compound can be prepared by oxidizing a compound represented by the 55 formula 3 EP 0 317 332 B1 NHSO2R1 I A-R5 IV 70 wherein R1 and A are as defined above, R5 is a cycloalkyl group substituted by a hydroxyl group, obtained in the item (1), and then subjecting to a nitration similar to that of the item (1). The oxidation used in this reaction may be an ordinary oxidation by which an alcohol is converted to a ketone, for example, methods using chromium trioxide (Jones reagent, Collins reagent and the like), potassium permanganate, manganese dioxide, dimethyl sulfoxide and the like. 75 (5) A compound of Formula I wherein R2 is -A-R3 (wherein A is a sulfinyl group or a sulfonyl group) can be prepared by oxidizing the compound of Formula I wherein R2 is - S - R3 obtained in the above item (1) in accordance with an ordinary oxidation, for example, methods using hydrogen peroxide, peracetic acid, m -chloroperbenzoic acid, potassium permanganate, sodium periodate and the like. (6) A compound of Formula I wherein B is a carbonyl group can be prepared from 2-aminobenzonitrile 20 as a starting material. More specially, 2-aminobenzonitrile is reacted with an organometallic compound containing the group R+, and hydrolyzed to give a 2-cycloalkylcarbonylaniline compound. Examples of the organometallic compound containing the group R+ in this reaction are Grignard reagents, or- ganolithium compounds or organocopper compounds such as cyclopentyl magnesium bromide, cyclohexylmagnesium chloride, cyclohexylmagnesium bromide, cyclopentyllithium, cyclohexyllithium, 25 lithium dicyclohexyl cuprate and the like.
Load more

Recommended publications
  • INDEX to PESTICIDE TYPES and FAMILIES and PART 180 TOLERANCE INFORMATION of PESTICIDE CHEMICALS in FOOD and FEED COMMODITIES
    US Environmental Protection Agency Office of Pesticide Programs INDEX to PESTICIDE TYPES and FAMILIES and PART 180 TOLERANCE INFORMATION of PESTICIDE CHEMICALS in FOOD and FEED COMMODITIES Note: Pesticide tolerance information is updated in the Code of Federal Regulations on a weekly basis. EPA plans to update these indexes biannually. These indexes are current as of the date indicated in the pdf file. For the latest information on pesticide tolerances, please check the electronic Code of Federal Regulations (eCFR) at http://www.access.gpo.gov/nara/cfr/waisidx_07/40cfrv23_07.html 1 40 CFR Type Family Common name CAS Number PC code 180.163 Acaricide bridged diphenyl Dicofol (1,1-Bis(chlorophenyl)-2,2,2-trichloroethanol) 115-32-2 10501 180.198 Acaricide phosphonate Trichlorfon 52-68-6 57901 180.259 Acaricide sulfite ester Propargite 2312-35-8 97601 180.446 Acaricide tetrazine Clofentezine 74115-24-5 125501 180.448 Acaricide thiazolidine Hexythiazox 78587-05-0 128849 180.517 Acaricide phenylpyrazole Fipronil 120068-37-3 129121 180.566 Acaricide pyrazole Fenpyroximate 134098-61-6 129131 180.572 Acaricide carbazate Bifenazate 149877-41-8 586 180.593 Acaricide unclassified Etoxazole 153233-91-1 107091 180.599 Acaricide unclassified Acequinocyl 57960-19-7 6329 180.341 Acaricide, fungicide dinitrophenol Dinocap (2, 4-Dinitro-6-octylphenyl crotonate and 2,6-dinitro-4- 39300-45-3 36001 octylphenyl crotonate} 180.111 Acaricide, insecticide organophosphorus Malathion 121-75-5 57701 180.182 Acaricide, insecticide cyclodiene Endosulfan 115-29-7 79401
    [Show full text]
  • Kinetic and Mechanistic Study of the Reaction Between Methane Sulfonamide (CH3S(O)2NH2) and OH
    Atmos. Chem. Phys., 20, 2695–2707, 2020 https://doi.org/10.5194/acp-20-2695-2020 © Author(s) 2020. This work is distributed under the Creative Commons Attribution 4.0 License. Kinetic and mechanistic study of the reaction between methane sulfonamide (CH3S.O/2NH2) and OH Matias Berasategui, Damien Amedro, Achim Edtbauer, Jonathan Williams, Jos Lelieveld, and John N. Crowley Division of Atmospheric Chemistry, Max-Planck-Institut für Chemie, 55128 Mainz, Germany Correspondence: John N. Crowley ([email protected]) Received: 8 November 2019 – Discussion started: 28 November 2019 Revised: 30 January 2020 – Accepted: 3 February 2020 – Published: 4 March 2020 Abstract. Methane sulfonamide (MSAM), CH3S.O/2NH2, The main organosulfur trace gases in the marine boundary was recently detected for the first time in ambient air over the layer are dimethyl sulfide (CH3SCH3, DMS) and its oxi- Red Sea and the Gulf of Aden where peak mixing ratios of dation products dimethyl sulfoxide (DMSO), dimethyl sul- ≈ 60 pptv were recorded. Prior to this study the rate constant fone (DMSO2), methyl sulfonic acid (MSA), and methyl for its reaction with the OH radical and the products thereby sulfinic acid (MSI) for which atmospheric lifetimes with re- formed were unknown, precluding assessment of its role in spect to their degradation by the OH radical vary between the atmosphere. We have studied the OH-initiated photo- hours (DMS) and several weeks (DMSO2). oxidation of MSAM in air (298 K, 700 Torr total pressure) Recently, the first detection of methane sulfonamide in a photochemical reactor using in situ detection of MSAM (CH3S.O/2NH2, MSAM) in ambient air was made during and its products by Fourier transform infrared (FTIR) absorp- the Air Quality and Climate Change in the Arabian Basin tion spectroscopy.
    [Show full text]
  • Synthesis and Herbicidal Activity of Sulfonanilides Having a Pyrimidinyl-Containing Group at the 2-Position
    J. Pestic. Sci., 36(2), 212–220 (2011) DOI: 10.1584/jpestics.G10-87 Original Article Synthesis and herbicidal activity of sulfonanilides having a pyrimidinyl-containing group at the 2؅-position Takumi YOSHIMURA,†* Masao NAKATANI,† Sohei ASAKURA,†† Ryo HANAI,†† Manabu HIRAOKA††† and Shigefumi KUWAHARA†††† † K-I Chemical Research Institute Co., Ltd., Iwata, Shizuoka 437–1213, Japan †† Life Science Research Institute, Kumiai Chemical Industry Co., Ltd., Kikugawa, Shizuoka 439–0031, Japan ††† Formulation Technology Institute, Kumiai Chemical Industry Co., Ltd., Shimizu, Shizuoka 424–0053, Japan †††† Graduate School of Agricultural Science, Tohoku University, Aoba-ku, Sendai 981–8555, Japan (Received October 27, 2010; Accepted November 16, 2010) A novel series of sulfonanilides having a pyrimidinyl-containing group at the 2Ј-position was prepared and their herbicidal activities against paddy weeds and selectivity against rice plants were assessed. The structure-activity relationships were probed by substitution of the sulfonyl group, bridge and benzene ring. Among the sulfon- amides, difluoromethyl compound showed comparatively high activity and a broad spectrum to control weeds, including Echinochloa oryzicola. The most preferable substitution position on the benzene ring was in the 6-po- sition and the lower alkyl group showed high herbicidal activity and a broad weed control spectrum, and among the compounds tested, the methoxymethyl group was the best. In respect of the bridge moiety, the hydroxyl group was the best. Among the compounds examined, 2Ј-[(4,6-dimethoxypyrimidin-2-yl)(hydroxy)methyl]-1,1- difluoro-6Ј-(methoxymethyl)methanesulfonanilide, applied at rates between 4 to 16 g a.i./ha, showed excellent pre-emergence herbicidal activity with a broad spectrum against grass, sedge and broadleaf weeds without injury to rice plants.
    [Show full text]
  • (MSAM), DMS and DMSO2 Measured in Air Over the Arabian Sea Achim Edtbauer1, Christof Stönner1, Eva Y
    A new marine biogenic emission: methane sulfonamide (MSAM), DMS and DMSO2 measured in air over the Arabian Sea Achim Edtbauer1, Christof Stönner1, Eva Y. Pfannerstill1, Matias Berasategui1, David Walter1,2, John N. Crowley1, Jos Lelieveld1,3, and Jonathan Williams1,3 1Atmospheric Chemistry Department, Max Planck Institute for Chemistry, Mainz, Germany 2Department Biogeochemical Processes, Max Planck Institute for Biogeochemistry, Jena, Germany 3Energy, Environment and Water Research Center, The Cyprus Institute, Nicosia, Cyprus Correspondence: Achim Edtbauer ([email protected]) Abstract. We present the first ambient measurements of a new marine emission methane sulfonamide (MSAM: CH5NO2S), along with dimethyl sulfide (DMS) and dimethyl sulfone (DMSO2) over the Arabian Sea. Two shipborne transects (W ! E, E ! W) were made during the AQABA (Air Quality and Climate Change in the Arabian Basin) measurement campaign. Molar mixing ratios in picomole of species per mole of air (throughout this manuscript abbreviated as ppt) of DMS were in the range 5 300–500 ppt during the first traverse of the Arabian Sea (first leg) and 100–300 ppt in the second leg. In the first leg DMSO2 was always below 40 ppt and MSAM was close to the limit of detection. During the second leg DMSO2 was between 40–120 ppt and MSAM was mostly in the range 20–50 ppt with maximum values of 60 ppt. An analysis of HYSPLIT back trajectories combined with calculations of the exposure of these trajectories to underlying chlorophyll in the surface water revealed that most MSAM originates from the Somalia upwelling region, known for its high biological activity. MSAM emissions can be as 10 high as one third of DMS emissions over the upwelling region.
    [Show full text]
  • IUPAC Provisional Recommendations
    Preferred IUPAC Names 177 Chapter 6, Sect 66 September, 2004 P-66 Amides, imides, hydrazides, nitriles, aldehydes, their chalcogen analogues and derivatives P-66.0 Introduction P-66.1 Amides P-66.2 Imides P-66.3 Hydrazides P-66.4 Amidines, amidrazones, hydrazidines P-66.5 Nitriles P-66.6 Aldehydes P-66.0 Introduction The classes dealt with in this Section have in common the fact that their retained names are derived from those of acids by changing the ‘ic acid’ ending to a class name, for example ‘amide’, ‘ohydrazide’, ‘nitrile’ or ‘aldehyde’. Their systematic names are formed substitutively by the suffix mode using one of two types of suffix, one that includes the carbon atom, for example, ‘carbonitrile’ for −CN, and one that does not, for example, ‘-nitrile’ for −(C)N,. Amidines are named as amides, hydrazidines as hydrazides, and amidrazones as amides or hydrazides. P-66.1 Amides P-66.1.0 Introduction P-66.1.1 Primary amides P-66.1.2 Secondary and tertiary amides P-66.1.3 Chalcogen analogues of amides P-66.1.4 Lactams, lactims, sultams and sultims P-66.1.5 Amides of carbonic, oxalic, cyanic, and polycarbonic acids P-66.1.6 Polyfunctional amides P-66.1.0 Introduction Amides are derivatives of oxoacids in which each hydroxy group has been replaced by an amino or substituted amino group. Chalcogen replacement analogues are called thio-, seleno- and telluroamides. Compounds having one, two or three acyl groups on a single nitrogen atom are generically included and may be designated as primary, secondary and tertiary amides, respectively.
    [Show full text]
  • Standard X-Ray Diffraction Powder Patterns NATIONAL BUREAU of STANDARDS
    NATIONAL INSTITUTE OF STANDARDS & TECHNOLOGY Research Information Center Gaithersburg, MD 20899 NATL INST OF STANDARDS & TECH R.I.C. A1 11 00988606 /NBS monograph QC100 .U556 V25-12;1975 C.1 NBS-PUB-C 19 NBS MONOGRAPH 25 " SECTION 12 U.S. DEPARTMENT OF COMMERCE / National Bureau of Standards Standard X-ray Diffraction Powder Patterns NATIONAL BUREAU OF STANDARDS 1 The National Bureau of Standards was established by an act of Congress March 3, 1901. The Bureau's overall goal is to strengthen and advance the Nation's science and technology and facilitate their effective application for public benefit. To this end, the Bureau conducts research and provides: (1) a basis for the Nation's physical measurement system, (2) scientific and technological services for industry and government, (3) a technical basis for equity in trade, and (4) technical services to promote public safety. The Bureau consists of the Institute for Basic Standards, the Institute for Materials Research, the Institute for Applied Technology, the Institute for Computer Sciences and Technology, and the Office for Information Programs. THE INSTITUTE FOR BASIC STANDARDS provides the central basis within the United States of a complete and consistent system of physical measurement; coordinates that system with measurement systems of other nations; and furnishes essential services leading to accurate and uniform physical measurements throughout the Nation's scientific community, industry, and commerce. The Institute consists of a Center for Radiation Research, an Office of Meas- urement Services and the following divisions: Applied Mathematics — Electricity — Mechanics — Heat — Optical Physics — Nuclear Sciences 2 — Applied Radiation 2 — Quantum Electronics 3 — Electromagnetics 3 — Time 3 3 3 and Frequency — Laboratory Astrophysics — Cryogenics .
    [Show full text]
  • Light in Gold Catalysis Sina Witzel, A
    pubs.acs.org/CR Review Light in Gold Catalysis Sina Witzel, A. Stephen K. Hashmi, and Jin Xie* Cite This: https://dx.doi.org/10.1021/acs.chemrev.0c00841 Read Online ACCESS Metrics & More Article Recommendations ABSTRACT: Within the wide family of gold-catalyzed reactions, gold photocatalysis intrinsically features unique elementary steps. When gold catalysis meets photocatalysis, a valence change of the gold center can easily be achieved via electron transfer and radical addition, avoiding the use of stoichiometric sacrificial external oxidants. The excellent compatibility of radicals with gold catalysts opens the door to a series of important organic transformations, including redox-neutral C−C and C−X coupling, C−H activation, and formal radical−radical cross-coupling. The photocatalysis with gold complexes nicely complements the existing photoredox catalysis strategies and also opens a new avenue for gold chemistry. This review covers the achieved transformations for both mononuclear gold(I) catalysts (with and without a photosensitizer) and dinuclear gold(I) photocatalysts. Various fascinating methodologies, their value for organic chemists, and the current mechanistic understanding are discussed. The most recent examples also demonstrate the feasibility of both, mononuclear and dinuclear gold(I) complexes to participate in excited state energy transfer (EnT), rather than electron transfer. The rare applications of gold(III) photocatalysts, both homogeneous and heterogeneous, are also summarized. CONTENTS Authors AZ Notes AZ 1. Introduction A Biographies AZ 1.1. Redox Au(I)/Au(III) Catalysis A Acknowledgments AZ 1.2. Gold Photoredox Catalysis B References AZ 2. Mononuclear Gold(I) Complexes D 2.1. Dual Gold/Photoredox Catalysis D 2.1.1.
    [Show full text]
  • Korea Industrial Tariff Schedule
    DRAFT Subject to Legal Review for Accuracy, Clarity, and Consistency Annex 2-B Industrial Schedule for the Republic of Korea Staging HSK 10 Description Base Rate Category 0301101000 Gold carp 10 C 0301102000 Tropical fish 10 C 0301109000 Other 10 A 0301911000 Salmo trutta, Oncorhynchus mykiss,Oncorhynchus clarki, Oncorhynchus 10 C aguabonita,Oncorhynchus gilae 0301912000 Oncorhynchus apache and Oncorhynchus chrysogaster 10 C 0301921000 Glass eel 10 A 0301929000 Other 30% or I ￦1,908/kg 0301930000 Carp 10 C 0301992000 Yellow tail 10 A 0301994000 Sea-bream 45% or G ￦3,292/kg 0301995000 Conger eel 10 G 0301996000 Sharp toothed eel 10 G 0301997000 Salad eel 10 C 0301998000 Flat fish 10 C 0301999010 True bass 10 G 0301999020 Puffers 10 G 0301999030 Tilapia 10 C 0301999040 Rock fish(including pacific ocean perch) 10 C 0301999050 Sea bass 40 C 0301999060 Mullets 10 C 0301999070 Loaches 10 C 0301999080 Cat fishes 10 A 0301999091 Rock Trout(Hexagrammos spp., Agrammus spp.) 10 C 0301999092 Crusian carp 10 C 0301999093 Salmon 10 A 0301999094 Grass carp 10 A 0301999095 Croakers 36 G 0301999099 Other 10 G 0302111000 Salmo trutta, Oncorhynchus mykiss, Oncorhynchus clarki,Oncorhynchus 20 G aquabonita, Oncorhynchus gilae 0302112000 Oncorhynchus apache and Oncorhynchus chrysogaster 20 A 0302120000 Pacific salmon(Oncorhynchus nerka, Oncorhynchus gorbuscha, Oncorhynchus 20 A keta, Oncorhynchus tschawytscha, Oncorhynchus kisutch, Oncorhynchus masou and Oncorhynchus rhodurus), Atlantic salmon(Salmo salar)and Danube salmon(Hucho hucho) 0302190000 Other 20
    [Show full text]
  • Which Diuretics Are Safe and Effective for Patients with a Sulfa Allergy?
    From the CLINIcAL InQUiRiES Family Physicians Inquiries Network Ron Healy, MD University of Washington, Which diuretics are safe Seattle; Alaska Family Medicine Residency, Anchorage and effective for patients Terry Ann Jankowski, MLS University of Washington, Seattle with a sulfa allergy? Evidence-based answer Diuretics that do not contain a sulfonamide subsequent allergic reactions to commonly group (eg, amiloride hydrochloride, used sulfonamide-containing diuretics eplerenone, ethacrynic acid, spironolactone, (eg, carbonic anhydrase inhibitors, loop and triamterene) are safe for patients with an diuretics, and thiazides) (strength of allergy to sulfa. The evidence is contradictory recommendation: C, based on case series ® as to whether a history Dowdenof allergy to Healthand poor Media quality case-control and cohort sulfonamide antibiotics increases the risk of studies). Copyright Clinical commentaryFor personal use only Are all sulfa drugs created equal? agents and off-patent, with no company Historical bromides commonly fall by the to take up their cause, no one has been FAST TRACK wayside as better evidence becomes willing to challenge outdated package Reasonable available. Who would have thought 15 insert warnings. years ago that we would be promoting As clinicians who regularly work evidence supports beta-blockers for patients with congestive without a net, we are accustomed to what many of us heart failure? prescribing medications in less than ideal are doing: Using Likewise, with closer inspection, we circumstances. Thankfully, reasonable cheap thiazides have learned that not all sulfa drugs are evidence is available to support what many created equal. The stereospecificity due of us are already doing—using cheap for patients to the absence of aromatic amines in thiazides for patients despite a history of with a history common diuretics means they are safe sulfa allergy.
    [Show full text]
  • Alkyl Mercury-Induced Toxicity: Multiple Mechanisms of Action
    Alkyl Mercury-Induced Toxicity: Multiple Mechanisms of Action John F. Risher and Pamela Tucker Contents 1 Preface 1.1 How Alkyl Mercury Compounds Get into the Food Web 2 Introduction 3 Methylmercury: Mechanisms of Toxic Action 3.1 Altered Membrane Permeability 3.2 Altered Intracellular Calcium Homeostasis 3.3 Oxidative Stress/Reactive Oxygen Species (ROS) 3.4 Effects on Receptor Binding/Neurotransmitter Release 3.5 Effects Involving Arachidonic Acid 3.6 Effects on Cell Cycle/Cell Division 3.7 Effects on Glutathione (GSH) Activity 3.8 Involvement with Nitric Oxide Synthetase 3.9 Effects on Glial Cells and Glutamate-Glutamine Uptake and Homeostasis 3.10 Other Mechanisms 4 Ethylmercury: Mechanisms of Toxic Action 4.1 Mobilization of Intracellular Ca++ 4.2 Effects on Mitochondria (Membrane and ROS) 4.3 Effects on Arachidonic Acid, Leukotriene Synthesis, and Membrane Integrity 4.4 Effects on Glutathione (GSH) 4.5 Effects on Glutamate Transport 4.6 Effects on Neurotransmitter Availability 5 Summary and Conclusions References J.F. Risher (*) • P. Tucker Division of Toxicology and Human Health Sciences, Agency for Toxic Substances and Disease Registry, 1600 Clifton Road (MS F-58), Atlanta, GA 30333, USA e-mail: [email protected]; [email protected] © Springer International Publishing 2016 Reviews of Environmental Contamination and Toxicology, DOI 10.1007/398_2016_1 J.F. Risher and P. Tucker Abstract There are a number of mechanisms by which alkylmercury compounds cause toxic action in the body. Collectively, published studies reveal that there are some similarities between the mechanisms of the toxic action of the mono-alkyl mercury compounds methylmercury (MeHg) and ethylmercury (EtHg).
    [Show full text]
  • Analysis of US FDA-Approved Drugs Containing Sulfur Atoms
    Top Curr Chem (Z) (2018) 376:5 https://doi.org/10.1007/s41061-018-0184-5 REVIEW Analysis of US FDA‑Approved Drugs Containing Sulfur Atoms Kevin A. Scott1,2 · Jon T. Njardarson1 Received: 20 November 2017 / Accepted: 5 January 2018 / Published online: 22 January 2018 © Springer International Publishing AG, part of Springer Nature 2018 Abstract In this review, we discuss all sulfur-containing FDA-approved drugs and their structures. The second section of the review is dedicated to structural analy- sis and is divided into 14 subsections, each focusing on one type of sulfur-contain- ing moiety. A concise graphical representation of each class features drugs that are organized on the basis of structural similarity, evolutionary relevance, and medical indication. This review ofers a unique and comprehensive overview of the struc- tural features of all sulfur-containing FDA-approved drugs to date. Keywords Sulfonamide · Thioether · Sulfoxide · Sulfone · Sulfate · Sulfur heterocycle Abbreviations 6-APA 6-Aminopenicillanic acid ADP Adenosine diphosphate cGMP Cyclic guanosine monophosphate COX-2 Cyclooxygenase-2 GERD Gastroesophageal refux disease GPCR G protein-coupled receptor HIV Human immunodefciency virus mRNA Messenger RNA NSAID Nonsteroidal anti-infammatory drugs SMN1 Survival motor neuron 1 This article is part of the Topical Collection “Sulfur Chemistry”, edited by Xuefeng Jiang. * Jon T. Njardarson [email protected] 1 Department of Chemistry and Biochemistry, University of Arizona, Tucson, AZ 85721, USA 2 Department of Pharmacology
    [Show full text]
  • (12) United States Patent (10) Patent No.: US 8,298,992 B2 Stern Et Al
    US008298.992B2 (12) United States Patent (10) Patent No.: US 8,298,992 B2 Stern et al. (45) Date of Patent: Oct. 30, 2012 (54) LOW ODOR, LOW VOLATILITY SOLVENT (56) References Cited FOR AGRICULTURAL CHEMICALS U.S. PATENT DOCUMENTS (75) Inventors: Alan J. Stern, Magnolia, TX (US); 2,778,826 A * 1/1957 Schmidle ...................... 546,192 David Ferguson, Spring, TX (US); 3,074,940 A * 1/1963 Benzing ............. ... 544,178 Howard Stridde, George West, TX (US) 3,342,673 A * 9, 1967 Kaufman et al. ............. 514,443 5,283,229 A 2/1994 Narayanan et al. (73) Assignee: Huntsman Petrochemical LLC. The 2005, 0137091 A1 6, 2005 Herold et al. Woodlands, TX (US) 2005/0215433 A1 9, 2005 Benitez et al. (*) Notice: Subject to any disclaimer, the term of this OTHER PUBLICATIONS patent is extended or adjusted under 35 Masuyama A. Preparation and Surface Active Properties of Terminal U.S.C. 154(b) by 743 days. Amide Type of Alcohol Ethoxylates, Jun. 1989, JAOCS, vol. 66, No. (21) Appl. No.: 12/300,482 6, pppp. 834-837.* * cited by examiner (22) PCT Filed: May 25, 2007 86) PCT No.: PCT/US2007/069793 Primary Examiner — Brian-Yong S Kwon (86) O Assistant Examiner — Andriae M Holt S371 (c)(1), (74) Attorney, Agent, or Firm — Huntsman International (2), (4) Date: Nov. 12, 2008 LLC (87) PCT Pub. No.: WO2007/140332 (57) ABSTRACT PCT Pub. Date: Dec. 6, 2007 A composition includes an agricultural component in an (65) Prior Publication Data amount of at least about 27% by weight and a solvent com position in an amount not greater than about 55% by weight.
    [Show full text]