CH488657A - Process for the production of new amines - Google Patents

Process for the production of new amines

Info

Publication number
CH488657A
CH488657A CH1583369A CH1583369A CH488657A CH 488657 A CH488657 A CH 488657A CH 1583369 A CH1583369 A CH 1583369A CH 1583369 A CH1583369 A CH 1583369A CH 488657 A CH488657 A CH 488657A
Authority
CH
Switzerland
Prior art keywords
radical
hydroxy
isopropylamino
propane
salts
Prior art date
Application number
CH1583369A
Other languages
German (de)
Inventor
Ulrich Dr Daeniker Hans
Karl Dr Schenker
Paul Dr Schmidt
Max Dr Wilhelm
Original Assignee
Ciba Geigy
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from CH1179964A external-priority patent/CH465640A/en
Application filed by Ciba Geigy filed Critical Ciba Geigy
Priority to CH1583369A priority Critical patent/CH488657A/en
Publication of CH488657A publication Critical patent/CH488657A/en

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/13—Amines
    • A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/13—Amines
    • A61K31/14—Quaternary ammonium compounds, e.g. edrophonium, choline
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/47—Quinolines; Isoquinolines
    • A61K31/485—Morphinan derivatives, e.g. morphine, codeine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
    • A61K31/52—Purines, e.g. adenine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
    • C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
    • C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
    • C07D303/24—Ethers with hydroxy compounds containing no oxirane rings with polyhydroxy compounds

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Organic Chemistry (AREA)
  • Emergency Medicine (AREA)
  • Molecular Biology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

  

  Verfahren     zur        Herstellung    neuer Amine    Gegenstand der Erfindung ist ein Verfahren zur  Herstellung der       1-Isopropylamino-2-hydroxy-3-(o-nieder-          alkoxymethyl-phenoxy)-propane     der Formel  
EMI0001.0004     
    worin R einen niederen Alkylrest, wie einen Äthyl-,  Propyl- oder Butylrest, vor allem aber den Methylrest  bedeutet, insbesondere also des     1-Isopropylamino-2-          hydroxy-3-(o-methoxymethyl-phenoxy)-propans,    und  ihrer Salze.  



  Die neuen Verbindungen, besonders das       1-Isopropylamino-2-hydroxy-3-(o-methoxymethyl-          phenoxy)-propan     oder das       1-Isopropylamino-2-hydroxy-3-(o-n-butoxymethyl-          phenoxy)-propan,     besitzen wertvolle pharmakologische Eigenschaften. Ins  besondere bewirken sie eine Hemmung adrenergischer  ss-Rezeptoren. So hemmen sie z. B. an der mit Dial  narkotisierten Katze durch Isoproterenol hervorgerufene  Blutdrucksenkungen in Dosen von 0,01-1 mg/kg i. v.  Die Verbindungen können daher bei Herz- und Kreis  lauferkrankungen als Medikamente angewendet wer  den.  



  Das erfindungsgemässe Verfahren zur Herstellung  der neuen Verbindungen ist dadurch gekennzeichnet,  dass man in einem entsprechenden     1-Isopropylamino-2-          hydroxy-3-(o-niederalkoxymethyl-phenoxy)-propan,    das  an der 2-Hydroxylgruppe einen durch Hydrolyse oder  Hydrogenolyse abspaltbaren Rest aufweist, diesen Rest  durch Hydrolyse oder Hydrogenolyse abspaltet.  



  Durch Hydrolyse oder Hydrogenolyse abspaltbare    Reste sind z. B. a-Aralkylreste, wie Benzylreste,     Oxy-          carbonylreste,    wie a-Aralkoxycarbonylreste, z. B.     Car-          bobenzoxyreste,    oder Carbalkoxyreste, wie tert.     Butyl-          oxycarbonylreste,    oder Acylreste von Carbonsäuren,  z. B. niedere Alkanoylreste, wie der Acetylrest.  



  Die Hydrolyse und Hydrogenolyse können in übli  cher Weise, letztere besonders katalytisch z. B. mit  Palladium-Tierkohle, Platinoxyd oder Raney-Nickel  vorgenommen werden.  



  Je nach den     Verfahrensbedingungen    und Ausgangs  stoffen erhält man die Endstoffe in freier Form oder  in der ebenfalls in der Erfindung inbegriffenen Form  ihrer Salze. Die Salze der Erdstoffe können in an sich  bekannter \reise, z. B. mit Alkalien oder     Ionenaustau-          schern,    in die freien Basen übergeführt werden. Von  den letzteren lassen sich durch Umsetzung mit orga  nischen oder anorganischen Säuren, insbesondere sol  chen, die zur Bildung von therapeutisch     verwendbaren     Salzen geeignet sind, Salze gewinnen.

   Als solche Säuren  seien beispielsweise genannt: Halogenwasserstoffsäuren,  Schwefelsäuren, Phosphorsäuren, Salpetersäure, Per  chlorsäure, aliphatische, alicyclische, aromatische oder  heterocyclische Carbon- oder Sulfonsäuren, wie Amei  sen-, Essig-, Propion-, Bernstein-, Glykol-, Milch-,  Äpfel-, Wein-, Zitronen-, Ascorbin-, Malein-,     Hydroxy-          malein-    oder Bronztraubersäure;

   Phenylessig-, Benzoc-,  p-Amino-benzoe-, Anthranil-, p-Hydroxy-benzoe-,     Sali-          cyl-    oder p-Amino-salicylsäure, Embonsäure,     Methan-          sulfon-,    Äthansulfon-, Hydroxyäthansulfon-,     Äthylen-          sulfonsäure;    Halogenbenzolsulfon-, Toluolsulfon-,     Naph-          thalinsulfonsäure    oder Sulfanilsäure; Methionin,     Trypto-          phan,        Lysin    oder     Arginin.     



  Diese oder     andere    Salze der neuen Verbindungen,       wie    z. B. die     Pikrate,    können auch zur     Reinigung    der  erhaltenen freien Basen dienen, indem man die freien  Basen in Salze überführt, diese abtrennt und aus den  Salzen wiederum die Basen freimacht. Infolge der engen  Beziehungen zwischen den neuen     Verbindungen    in  freier Form und in Form ihrer Salze sind im voraus-      gegangenen und nachfolgend unter den freien Basen  sinn- und zweckmässig gegebenenfalls auch die entspre  chenden Salze zu verstehen.  



  Die neuen Verbindungen können als Racemate oder  in Form der Antipoden vorliegen. Das Racemat lässt  sich in üblicher Weise in die Antipoden zerlegen.  



  Die neuen Verbindungen können z. B. in Form  pharmazeutischer Präparate Verwendung finden, welche  sie in freier Form oder gegebenenfalls in Form ihrer  Salze in Mischung mit einem für die enterale oder  parenterale Applikation geeigneten pharmazeutischen  organischen oder anorganischen, festen oder flüssigen  Trägermaterial enthalten.  



  Die Ausgangsstoffe sind bekannt oder können, falls  sie neu sind, nach an sich bekannten Methoden erhalten  werden.  



  Verbindungen, die an der 2-Hydroxylgruppe einen  durch Hydrolyse oder Hydrogenolyse abspaltbaren  Rest aufweisen, erhält man z. B. durch Kondensation  einer Verbindung der Formel  
EMI0002.0000     
    mit einer Verbindung der Formel  
EMI0002.0001     
    worin R die oben gegebene Bedeutung besitzt,     X'2    für  einen durch Hydrolyse oder Hydrogenolyse abspaltbaren  Rest und einer der Reste X, und     Y,    für eine reaktions  fähig veresterte Hydroxylgruppe steht und der andere  die Aminogruppe bedeutet.  



  Reaktionsfähig veresterte Hydroxylgruppen sind ins  besondere solche, die mit einer starken organischen  oder anorganischen Säure, wie vor allem einer Halogen  wasserstoffsäure, z. B. der Chlor-, Brom- oder     Jodwas-          serstoffsäure,    oder einer Sulfonsäure, wie einer     Aryl-          sulfonsäure,    z. B. der p-Toluolsulfonsäure verestert sind.  



  Ferner sind diese an der 2-Hydroxylgruppe substi  tuierten Verbindungen auch dadurch erhältlich, dass man  ein o-(Niederalkoxymethyl)-phenol oder ein Salz davon  mit einer Verbindung der Formel  
EMI0002.0008     
    Umsetzt, worin X eine reaktionsfähig veresterte Hy  droxylgruppe und X.,' ein durch Hydrolyse oder     Hydro-          genolyse    abspaltbarer Rest ist.  



  Im folgenden Beispiel sind die Temperaturen in  Celsiusgraden angegeben.  



       Beispiel     12,0 g     1-Isopropylamino-2-acetoxy-3-(o-methoxy-          methyl-phenoxy)-propan    werden in 100 ml Äthanol  gelöst und nach Zugabe von 30 ml 2-n Natronlauge  während einer Stunde unter Rückfluss erhitzt. Hierauf  dampft man im Vakuum ein, kristallisiert den Rück-    stand aus Petroläther um und sublimiert. Man erhält  das     1-Isopropylamino-2-hydroxy-3-(o-methoxymethyl-          phenoxy)-propan    der Formel  
EMI0002.0016     
    das bei 49-51' schmilzt.  



  Auf analoge Weise kann man das       1-Isopropylamino-2-hydroxy-3-(o-n-butoxymethyl-          phenoxy)-propan     herstellen, das bei 130-135 /0,02 mm destilliert und  bei 40-45' schmilzt.



  Process for the preparation of new amines The invention relates to a process for the preparation of the 1-isopropylamino-2-hydroxy-3- (o-lower-alkoxymethyl-phenoxy) propanes of the formula
EMI0001.0004
    where R is a lower alkyl radical, such as an ethyl, propyl or butyl radical, but above all the methyl radical, in particular of 1-isopropylamino-2-hydroxy-3- (o-methoxymethylphenoxy) propane and their salts.



  The new compounds, especially 1-isopropylamino-2-hydroxy-3- (o-methoxymethylphenoxy) propane or 1-isopropylamino-2-hydroxy-3- (on-butoxymethylphenoxy) propane, have valuable pharmacological properties Characteristics. In particular, they inhibit adrenergic SS receptors. So they inhibit z. B. in the cat anesthetized with Dial caused by isoproterenol decreases in blood pressure in doses of 0.01-1 mg / kg i. v. The compounds can therefore be used as drugs for heart and circulatory diseases.



  The process according to the invention for the preparation of the new compounds is characterized in that in a corresponding 1-isopropylamino-2-hydroxy-3- (o-lower alkoxymethyl-phenoxy) -propane, the residue on the 2-hydroxyl group which can be split off by hydrolysis or hydrogenolysis has, this residue splits off by hydrolysis or hydrogenolysis.



  Residues which can be split off by hydrolysis or hydrogenolysis are z. B. a-aralkyl, such as benzyl, oxy carbonyl, such as a-aralkoxycarbonyl, z. B. carbobenzoxy radicals, or carbalkoxy radicals, such as tert. Butyl oxycarbonyl radicals, or acyl radicals of carboxylic acids, eg. B. lower alkanoyl radicals, such as the acetyl radical.



  The hydrolysis and hydrogenolysis can be done in übli cher way, the latter particularly catalytically z. B. be made with palladium charcoal, platinum oxide or Raney nickel.



  Depending on the process conditions and starting materials, the end products are obtained in free form or in the form of their salts, which is also included in the invention. The salts of the earth can travel in a per se known, z. B. with alkalis or ion exchangers, are converted into the free bases. Of the latter, salts can be obtained by reaction with organic or inorganic acids, in particular those which are suitable for the formation of therapeutically useful salts.

   Examples of such acids are: hydrohalic acids, sulfuric acids, phosphoric acids, nitric acid, perchloric acid, aliphatic, alicyclic, aromatic or heterocyclic carboxylic or sulfonic acids, such as formic, acetic, propionic, succinic, glycolic, lactic, Malic, tartaric, citric, ascorbic, maleic, hydroxy-maleic or bronchial acid;

   Phenylacetic, benzoc, p-amino-benzoic, anthranil, p-hydroxy-benzoic, salicylic or p-amino-salicylic acid, emboxylic acid, methanesulphonic, ethanesulphonic, hydroxyethanesulphonic, ethylene sulphonic acid ; Halobenzenesulphonic, toluenesulphonic, naphthalenesulphonic acid or sulphanilic acid; Methionine, tryptophan, lysine or arginine.



  These or other salts of the new compounds, such as. B. the picrates, can also be used to purify the free bases obtained by converting the free bases into salts, separating them and in turn frees the bases from the salts. As a result of the close relationships between the new compounds in free form and in the form of their salts, in the preceding and in the following the free bases are meaningfully and appropriately also the corresponding salts.



  The new compounds can exist as racemates or in the form of the antipodes. The racemate can be broken down into the antipodes in the usual way.



  The new connections can e.g. B. in the form of pharmaceutical preparations are used which they contain in free form or optionally in the form of their salts in a mixture with a pharmaceutical organic or inorganic, solid or liquid carrier material suitable for enteral or parenteral administration.



  The starting materials are known or, if they are new, can be obtained by methods known per se.



  Compounds which have a residue on the 2-hydroxyl group which can be split off by hydrolysis or hydrogenolysis are obtained, for. B. by condensation of a compound of the formula
EMI0002.0000
    with a compound of the formula
EMI0002.0001
    where R has the meaning given above, X'2 stands for a radical which can be split off by hydrolysis or hydrogenolysis and one of the radicals X and Y stands for a reactive esterified hydroxyl group and the other stands for the amino group.



  Reactively esterified hydroxyl groups are in particular those that react with a strong organic or inorganic acid, such as a halogenated hydrochloric acid, eg. B. the chlorine, bromine or hydroiodic acid, or a sulfonic acid such as an aryl sulfonic acid, z. B. the p-toluenesulfonic acid are esterified.



  Furthermore, these compounds substituted on the 2-hydroxyl group can also be obtained by combining an o- (lower alkoxymethyl) phenol or a salt thereof with a compound of the formula
EMI0002.0008
    Reacts in which X is a reactive esterified hydroxyl group and X, 'is a radical which can be split off by hydrolysis or hydrogenolysis.



  In the following example the temperatures are given in degrees Celsius.



       Example 12.0 g of 1-isopropylamino-2-acetoxy-3- (o-methoxymethylphenoxy) propane are dissolved in 100 ml of ethanol and, after addition of 30 ml of 2N sodium hydroxide solution, heated under reflux for one hour. It is then evaporated in vacuo, the residue is recrystallized from petroleum ether and sublimed. 1-Isopropylamino-2-hydroxy-3- (o-methoxymethylphenoxy) propane of the formula is obtained
EMI0002.0016
    which melts at 49-51 '.



  1-Isopropylamino-2-hydroxy-3- (o-n-butoxymethylphenoxy) propane, which distills at 130-135 / 0.02 mm and melts at 40-45 ', can be prepared in an analogous manner.

Claims (1)

PATENTANSPRUCH Verfahren zur Herstellung der 1-Isopropylamino-2- hydroxy-3-(o-niederalkoxymethyl-phenoxy)-propane der Formel EMI0002.0021 worin R ein niederer Alkylrest ist, und ihrer Salze, dadurch gekennzeichnet, dass man in einem entspre chenden 1-Isopropylamino-2-hydroxy-3-(o-niederalkoxy- methyl-phenoxy)-propan, das an der 2-Hydroxylgruppe einen durch Hydrolyse oder Hydrogenolyse abspalt baren Rest aufweist, diesen Rest durch Hydrolyse oder Hydrogenolyse abspaltet. UNTERANSPRÜCHE 1. PATENT CLAIM Process for the preparation of the 1-isopropylamino-2-hydroxy-3- (o-lower alkoxymethyl-phenoxy) -propane of the formula EMI0002.0021 wherein R is a lower alkyl radical, and its salts, characterized in that one in a corre sponding 1-isopropylamino-2-hydroxy-3- (o-lower alkoxymethyl-phenoxy) -propane, which on the 2-hydroxyl group through Has hydrolysis or hydrogenolysis cleavable radical, cleaves this radical by hydrolysis or hydrogenolysis. SUBCLAIMS 1. Verfahren nach Patentanspruch, dadurch gekenn zeichnet, dass man ein 1-Isopropylamino-2-hydroxy-3- (o-niederalkoxymethyl-phenoxy)-propan, das an der 2-Hydroxylgruppe einen a-Arylalkylrest enthält, hydro- genolysiert. 2. Verfahren nach Patentanspruch, dadurch gekenn zeichnet, dass man in einem 1-Isopropylamino-2-hydr- oxy-3-(o-niederalkoxymethyl-phenoxy)-propan, das an der 2-Hydroxylgruppe einen Acylrest enthält, diesen abhydrolysiert. 3. Process according to patent claim, characterized in that a 1-isopropylamino-2-hydroxy-3- (o-lower alkoxymethyl-phenoxy) -propane which contains an α-arylalkyl radical on the 2-hydroxyl group is hydrogenolyzed. 2. The method according to claim, characterized in that in a 1-isopropylamino-2-hydroxy-3- (o-lower alkoxymethyl-phenoxy) -propane which contains an acyl radical on the 2-hydroxyl group, this is hydrolyzed. 3. Verfahren nach Patentanspruch oder Unteran spruch I oder 2, dadurch gekennzeichnet, dass man von Ausgangsstoffen ausgeht, in denen R der Methyl- rest ist. 4. Verfahren nach Patentanspruch oder Unteran spruch 1 oder 2, dadurch gekennzeichnet, dass man von Ausgangsstoffen ausgeht, in denen R der n-Butyl- rest ist. 5. Verfahren nach Patentanspruch oder Unteran spruch 1 oder 2, dadurch gekennzeichnet, dass man erhaltene Salze in die freien Basen umwandelt. 6. Verfahren nach Patentanspruch oder Unteran spruch I oder 2, dadurch gekennzeichnet, dass man erhaltene freie Basen in die Salze umwandelt. Process according to claim 1 or claim 1 or 2, characterized in that starting materials are used in which R is the methyl radical. 4. The method according to claim 1 or claim 2, characterized in that starting materials are used in which R is the n-butyl radical. 5. The method according to claim or sub-claim 1 or 2, characterized in that the salts obtained are converted into the free bases. 6. The method according to claim or sub-claim I or 2, characterized in that the free bases obtained are converted into the salts.
CH1583369A 1964-09-10 1965-07-09 Process for the production of new amines CH488657A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CH1583369A CH488657A (en) 1964-09-10 1965-07-09 Process for the production of new amines

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
CH1179964A CH465640A (en) 1964-09-10 1964-09-10 Process for the production of new amines
CH1114467A CH477400A (en) 1964-09-10 1964-09-10 Process for the production of new amines
CH1583369A CH488657A (en) 1964-09-10 1965-07-09 Process for the production of new amines
CH962865A CH485659A (en) 1964-09-10 1965-07-09 Process for the production of new amines

Publications (1)

Publication Number Publication Date
CH488657A true CH488657A (en) 1970-04-15

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Country Link
CH (1) CH488657A (en)

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