WO1995011249A1 - Nouveaux derives de l'acide 2,4-diphosphonoglutarique, procedes pur leur preparation et medicaments contenant ces composes - Google Patents

Nouveaux derives de l'acide 2,4-diphosphonoglutarique, procedes pur leur preparation et medicaments contenant ces composes Download PDF

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Publication number
WO1995011249A1
WO1995011249A1 PCT/EP1994/003434 EP9403434W WO9511249A1 WO 1995011249 A1 WO1995011249 A1 WO 1995011249A1 EP 9403434 W EP9403434 W EP 9403434W WO 9511249 A1 WO9511249 A1 WO 9511249A1
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WIPO (PCT)
Prior art keywords
diphosphono
glutaric acid
cycloalkyl
lower alkyl
hydrogen
Prior art date
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PCT/EP1994/003434
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German (de)
English (en)
Inventor
Angelika Esswein
Christos Tsaklakidis
Gerd Zimmermann
Frieder Bauss
Original Assignee
Boehringer Mannheim Gmbh
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
Application filed by Boehringer Mannheim Gmbh filed Critical Boehringer Mannheim Gmbh
Priority to AU78567/94A priority Critical patent/AU7856794A/en
Publication of WO1995011249A1 publication Critical patent/WO1995011249A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
    • C07F9/3839—Polyphosphonic acids
    • C07F9/3873—Polyphosphonic acids containing nitrogen substituent, e.g. N.....H or N-hydrocarbon group which can be substituted by halogen or nitro(so), N.....O, N.....S, N.....C(=X)- (X =O, S), N.....N, N...C(=X)...N (X =O, S)
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
    • C07F9/3839—Polyphosphonic acids
    • C07F9/386—Polyphosphonic acids containing hydroxy substituents in the hydrocarbon radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
    • C07F9/3839—Polyphosphonic acids
    • C07F9/3869—Polyphosphonic acids containing carboxylic acid or carboxylic acid derivative substituents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
    • C07F9/572—Five-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
    • C07F9/576—Six-membered rings
    • C07F9/58—Pyridine rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
    • C07F9/576—Six-membered rings
    • C07F9/59—Hydrogenated pyridine rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
    • C07F9/6503—Five-membered rings
    • C07F9/6506—Five-membered rings having the nitrogen atoms in positions 1 and 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6527—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07F9/6533—Six-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/655—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms
    • C07F9/65515—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a five-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having sulfur atoms, with or without selenium or tellurium atoms, as the only ring hetero atoms
    • C07F9/655345—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having sulfur atoms, with or without selenium or tellurium atoms, as the only ring hetero atoms the sulfur atom being part of a five-membered ring

Definitions

  • the present invention relates to new 2,4-diphosphonoglutaric acid derivatives, processes for their preparation and medicaments which contain these substances.
  • R hydrogen, lower alkyl, which may be replaced by hydroxy, alkoxy,
  • Amino, dialkylamino, alkylmercapto, alkylsulfinyl, alkanesulfonyl, cycloalkyl, aryl or a heterocyclic ring may be substituted, lower alkenyl, cycloalkyl, cycloalkenyl, aryl or a heterocyclic ring,
  • R ⁇ and R2 can each independently be hydrogen, lower alkyl, cycloalkyl or arylmethyl,
  • Lower alkyl should in all cases be a straight-chain or branched Ci-Cö-alkyl group, such as. B. methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl or hexyl, in particular methyl, ethyl, isopropyl, butyl and hexyl.
  • Lower alkenyl means unsaturated residues with 3 - 6 carbon atoms, such as. B. allyl, but-2-enyl, hexa-2,4-dienyl, but especially allyl.
  • Cycloalkyl means a 3- to 7-membered ring, such as the cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or cycloheptyl ring, preferably the cyclopentyl and cyclohexyl ring.
  • Cycloalkenyl is said to be an unsaturated 5-7 ring, such as the cyclopentenyl, cyclohexenyl and cycloheptenyl ring.
  • Alkoxy is understood to be radicals such as the methoxy, ethoxy, propoxy, isopropoxy, butoxy or pentoxy radical, in particular the methoxy, ethoxy, isopropoxy and butoxy radical.
  • Dialkylamino is said to be an amino group with two identical or different C1-C5 alkyl radicals, such as. B. dimethylamino, methylpropylamino, methylpenlylamino, diethylamino or dipropylamino, especially dimethylamino, methylpropylamino and methylpentylamino.
  • Alkyl mercapto, alkylsulfinyl or alkanesulfonyl are preferably methyl mercapto, methylsulfinyl or methanesulfonyl.
  • Aryl means the phenyl or naphthyl radical, which may be mono- or polysubstituted by lower alkyl, halogen, hydroxy, alkoxy, amino, dialkylamino, alkyl mercapto, alkylsulfinyl, alkanesulfonyl, carboxamido, which may be mono- or disubstituted by lower alkyl, Carboxyl, Alkoxycarbonvl or Cyano can be substituted.
  • a heterocyclic ring is a 5- to 7-membered, saturated or unsaturated ring, such as. B. the pyrrolidine, piperidine, azepine, tetrahydrofuran, tetrahydropyran, morpholine, dioxane, furan, thiophene, pyridine, pyrazole, imidazole, thiazole, oxazole, pyrimidine or Pyrazine ring, preferably the pyrrolidine, piperidine, morpholine, furan, thiophene, pyridine and imidazole ring to understand, where the ring system can be substituted one or more times by halogen, lower alkyl or alkoxy.
  • Halogen is said to represent fluorine, chlorine, bromine and iodine, in particular fluorine and chlorine.
  • R has the meaning given above and R ⁇ - R-5 are independently lower alkyl, cycloalkyl or arylmethyl, saponified to the corresponding acids of the general formula I, or
  • R ⁇ and R2 are lower alkyl, cycloalkyl or arylmethyl, a hexaester of the general formula II
  • R has the meaning given above and Rj - R5 is lower alkyl, cycloalkyl or arylmethyl, partially saponified to give diphosphonic acid dicarboxylic acid esters of the general formula I,
  • the complete saponification of the phosphonic and carboxylic acid esters described in process a can be carried out by boiling with hydrohalic acid, preferably with semi-concentrated hydrochloric acid.
  • the partial saponification of the phosphonic esters described in process b in the presence of the carbonic ester gauges is generally carried out without a solvent or in an inert solvent such as methylene chloride using a trimethylsilyl halide such as Trimethylsilyl bromide or iodide, at a temperature between - 50 ° C and room temperature, preferably at 0 ° C.
  • benzyl esters present in compounds of the general formula II can be hydrogenolytically in the presence of z.
  • B. convert palladium / carbon into the corresponding phosphonic or carboxylic acids.
  • salts especially mono- or dialkali or ammonium salts are used, which in the usual way, for. B. by titration of the connections with inorganic bases, such as. B. sodium or potassium hydrogen carbonate, sodium hydroxide solution, potassium hydroxide solution, aqueous Ammomak or amines, such as. B. trimethyl or triethylamine.
  • inorganic bases such as. B. sodium or potassium hydrogen carbonate, sodium hydroxide solution, potassium hydroxide solution, aqueous Ammomak or amines, such as. B. trimethyl or triethylamine.
  • the salts are usually cleaned by falling over from water / acetone.
  • calcium, magnesium or zinc salts can also be used, which are usually poorly soluble in water, but are sometimes also slightly soluble.
  • These salts can be prepared by adding a calcium, zinc or magnesium salt, such as. B. calcium carbonate, calcium hydrogen carbonate, calcium hydroxide, calcium chloride, zinc carbonate, zinc hydrogen carbonate, zinc hydroxide, zinc chloride, magnesium carbonate, magnesium hydrogen carbonate, magnesium hydroxide or magnesium chloride as an aqueous solution or suspension in a ratio of 1: 1 or 2: 1 with an aqueous solution or suspension of 2,4-diphosphonoglutaric acid Allows to stir 20 - 120 ° C, then the precipitate is suctioned off or the aqueous solution is then concentrated.
  • novel substances of formula I and their salts according to the invention can be in any liquid or solid form suitable for achieving an effective dose, e.g. B. orally, rectally, topically, parenterally, subcutaneously, ocular, nasally, buccally, intravenously and transdermally. All the usual forms of application are possible here, for example tablets, capsules, dragees, syrups, solutions, suspensions, plasters, etc. Water is preferably used as the injection medium, which contains the additives customary for injection solutions, such as stabilizers, solubilizers and buffers. Such additives are e.g. B.
  • Liquid carriers for injection solutions must be sterile and are preferably filled into ampoules. Solid carriers are e.g. B.
  • Preparations suitable for oral administration can optionally contain flavorings and sweeteners.
  • the dosage can depend on various factors, such as the mode of administration, species, age and / or individual condition.
  • the doses to be administered daily are approximately 10-1000 mg / person, preferably 100-500 mg / person and can be taken in one or more times distributed.
  • a pharmaceutical formulation of these 2,4-diphosphonoglutaric acids can also be administered intermittently.
  • Phosphonoacetic acid triethyl ester (2.0 ml, 10 mmol) is added to a suspension of sodium hydride (240 mg, 10 mmol) in 30 ml of methanol. After stirring for 30 min at room temperature, a solution of 10 mmol of ⁇ -phosphonoacrylate in 10 ml of methanol is slowly added dropwise. After 24 hours at room temperature, the mixture is concentrated, saturated ammonium chloride solution (20 ml) is added and the mixture is extracted with ethyl acetate (2 ⁇ 50 ml). The combined organic phases are dried over magnesium sulfate and concentrated. The residue is purified by chromatography on silica gel.
  • the presentation follows the general working instruction A.
  • the presentation follows the general working instruction A.
  • the presentation follows the general working instruction A.
  • the presentation follows the general working instruction A.
  • the presentation follows the general working instruction A.
  • the presentation follows the general working instruction A.
  • the presentation follows the general working instruction A.
  • the presentation follows the general working instruction A.
  • the presentation follows the general working instruction A.
  • rats are injected twice a week with increasing amounts of a solution of 3.7 x 10 5 Bq / ml (10 ⁇ Ci / ml) [7- H] tetracycline ([ 3 H] TC); New England Nuclear, Boston, MA) specific activity 679 mCi / mmol.
  • the volume per injection is increased from 50 ⁇ l / week to 250 ⁇ l in the fifth week and maintained for a further week.
  • the total amount of [ 3 H] TC applied was 20 ⁇ Ci per rat. Rats 51 days old are put into individual metabolism cages and fed a group with food containing 0.5% Ca and 0.35% P.
  • This feed was produced by adding appropriate amounts of calcium glucagonate and neutral sodium phosphate from feed with a low calcium and phosphate content (SODI 2134, Klingenthal mill).
  • SODI 2134 calcium and phosphate content
  • the animals received aqua dest. ad libitum.
  • the collection of the 24-hour urine was started after 61 days.
  • the urine was collected daily at 11 a.m. at that time the animals were also fed.
  • On the sixth day after the start of urine collection the animals received two sc injections with substance (at 8 a.m. and 5 p.m., respectively).
  • the inhibition of bone resorption is reduced by the [H] - Tetracycline excretion indicated on day 8 after the start of urine collection.
  • the 3 H-TC in the urine was determined by liquid scintillation by adding 10 ml of the scintillator Pico-Fluor 30 (packard International, Zurich, Switzerland) to 1 ml urine.
  • Example compound 2 20 2 x 6 mg / kg mg / kg

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Composés de formule (I) dans laquelle: R représente hydrogène, alkyle inférieur pouvant être éventuellement remplacé par un hydroxy, un alcoxy, un amino, un dialkylamino, un alkylmercapto, un alkylsulfinyle, un alcanosulfonyle, un cycloalkyle, un aryle ou un composé hétérocyclique, un alcényle inférieur, un cycloalkyle, un cycloalcényle, un aryle ou un composé hétérocyclique; R1 et R2 peuvent représenter, indépendamment l'un de l'autre, hydrogène, un alkyle inférieur, un cycloalkyle ou un arylméthyle, ainsi que leurs sels acceptables sur le plan pharmacologique. L'invention concerne également des procédés pour la préparation de ces composés, et des médicaments les contenant utilisés dans le traitement des troubles métaboliques relatifs au calcium.
PCT/EP1994/003434 1993-10-22 1994-10-19 Nouveaux derives de l'acide 2,4-diphosphonoglutarique, procedes pur leur preparation et medicaments contenant ces composes WO1995011249A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU78567/94A AU7856794A (en) 1993-10-22 1994-10-19 2,4-diphosphonoglutaric acid derivatives, methods of preparing them and drugs containing them

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DEP4336099.8 1993-10-22
DE4336099A DE4336099A1 (de) 1993-10-22 1993-10-22 Neue 2.4-Diphosphonoglutarsäurederivate, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Arzneimittel

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WO1995011249A1 true WO1995011249A1 (fr) 1995-04-27

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PCT/EP1994/003434 WO1995011249A1 (fr) 1993-10-22 1994-10-19 Nouveaux derives de l'acide 2,4-diphosphonoglutarique, procedes pur leur preparation et medicaments contenant ces composes

Country Status (3)

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AU (1) AU7856794A (fr)
DE (1) DE4336099A1 (fr)
WO (1) WO1995011249A1 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19902924A1 (de) * 1999-01-26 2000-08-03 Hassan Jomaa Verwendung von phosphororganischen Verbindungen zur prophylaktischen und therapeutischen Behandlung von Infektionen

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5567747A (en) * 1978-11-15 1980-05-22 Konishiroku Photo Ind Co Ltd Developing solution for silver halide color photographic material
WO1993012122A1 (fr) * 1991-12-19 1993-06-24 Boehringer Mannheim Gmbh Nouveaux derives de l'acide phosphonosuccinique, leur procede de fabrication et medicaments renfermant ces composes
WO1993024131A1 (fr) * 1992-05-29 1993-12-09 Procter & Gamble Pharmaceuticals, Inc. Composes de phosphonocarboxylate destines au traitement d'anomalies du metabolisame du calcium et du phosphate

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5567747A (en) * 1978-11-15 1980-05-22 Konishiroku Photo Ind Co Ltd Developing solution for silver halide color photographic material
WO1993012122A1 (fr) * 1991-12-19 1993-06-24 Boehringer Mannheim Gmbh Nouveaux derives de l'acide phosphonosuccinique, leur procede de fabrication et medicaments renfermant ces composes
WO1993024131A1 (fr) * 1992-05-29 1993-12-09 Procter & Gamble Pharmaceuticals, Inc. Composes de phosphonocarboxylate destines au traitement d'anomalies du metabolisame du calcium et du phosphate

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, vol. 099, no. 9, 29 August 1983, Columbus, Ohio, US; abstract no. 070845, PETROV K A ET AL: "Diethyl ester of 2,4-bis(diethoxyphosphinyl)pimelic acid" *
SAUL PATAI: "Condensation of triethyl phosphonoacetate with aromatic aldehydes", JOURNAL OF ORGANIC CHEMISTRY, vol. 25, 1960, EASTON US, pages 1232 - 1234 *
ZH. OBSHCH. KHIM. (ZOKHA4,0044460X);83; VOL.53 (3); PP.704-5, USSR (SU) *

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AU7856794A (en) 1995-05-08

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