CH509991A - Sulphonamides and process for the manufacture thereof - Google Patents

Sulphonamides and process for the manufacture thereof

Info

Publication number
CH509991A
CH509991A CH787469A CH787469A CH509991A CH 509991 A CH509991 A CH 509991A CH 787469 A CH787469 A CH 787469A CH 787469 A CH787469 A CH 787469A CH 509991 A CH509991 A CH 509991A
Authority
CH
Switzerland
Prior art keywords
groups
toluenesulfonyl
symbol
preparation
sodium borohydride
Prior art date
Application number
CH787469A
Other languages
German (de)
Inventor
Bretschneider Hermann Dr Prof
Helmut Dr Egg
Peter Dr Quitt
Original Assignee
Hoffmann La Roche
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 CH1136566A external-priority patent/CH500176A/en
Priority to CH787469A priority Critical patent/CH509991A/en
Priority to CH787169A priority patent/CH510647A/en
Priority to CH787569A priority patent/CH509992A/en
Priority to CH787269A priority patent/CH510648A/en
Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche
Priority to CH787369A priority patent/CH509990A/en
Priority to SE10481/67A priority patent/SE334354B/xx
Priority to IL28401A priority patent/IL28401A/en
Priority to DE1967H0063446 priority patent/DE1668199B2/en
Priority to NL6710676A priority patent/NL6710676A/xx
Priority to BE702280D priority patent/BE702280A/xx
Priority to GB50521/68A priority patent/GB1147405A/en
Priority to GB35845/67A priority patent/GB1147403A/en
Priority to GB50520/68A priority patent/GB1147404A/en
Priority to ES343910A priority patent/ES343910A1/en
Priority to DK401867AA priority patent/DK122761B/en
Priority to JP5054967A priority patent/JPS5516575B1/ja
Priority to FR117194A priority patent/FR1546595A/en
Priority to FR117192A priority patent/FR7148M/fr
Publication of CH509991A publication Critical patent/CH509991A/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
    • 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
    • A61K31/64—Sulfonylureas, e.g. glibenclamide, tolbutamide, chlorpropamide
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/50—Compounds containing any of the groups, X being a hetero atom, Y being any atom
    • C07C311/52—Y being a hetero atom
    • C07C311/54—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea
    • C07C311/57—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea having sulfur atoms of the sulfonylurea groups bound to carbon atoms of six-membered aromatic rings
    • C07C311/59—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea having sulfur atoms of the sulfonylurea groups bound to carbon atoms of six-membered aromatic rings having nitrogen atoms of the sulfonylurea groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D263/28—Nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
    • C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

(A) Cpds. of the formulae:- (I) R1 = H R2 = OH, or together with R' = keto R3 = phenyl opt. subst. by one or more halogen, lower alkyl, lower alkoxy, lower alkylthio, acetyl, amino, acylamino, diacylimido, or lower alkoxy and/or halogen substd. benzamidoethyl; 5-6 membered nitrogen heterocycle attached by the nitrogen atom n = 3 or 4. (B) N-(p-Chlorobenzenesulphonyl)-3,5-dimethyl-1-pyrazole carboxamide. Cpds. I and VI have blood-sugar depressing activity.

Description

  

  
 



  Verfahren zur Herstellung von Sulfonamiden
Die vorliegende Erfindung betrifft ein Verfahren zur Herstellung von Sulfonylharnstoffderivaten der Formel I
EMI1.1     
 in der R Phenyl, das durch Halogen, Niederalkyl-, Niederalkoxy-, Niederalkylthio-, Acetyl-, Amino-, Acylaminooder Diacylimidogruppen substituiert sein kann, und n die Zahl 3 oder 4 bedeutet.



   Das erfindungsgemässe Verfahren ist dadurch gekennzeichnet, dass man ein entsprechendes o-Oxo-cyclopentylbzw. -cyclohexyl-Derivat reduziert.



   Die erfindungsgemässe Reduktion kann z.B. durch Behandlung mit einem komplexen Metalhydrid, wie Natriumborhydrid, bewerkstelligt werden.



   Unter niederen Alkylgruppen, die in durch das Symbol R repräsentierten Resten enthalten sind, sollen geradkettige oder verzweigte Alkylgruppen   mitl -6      Kohlenstoff-    atomen verstanden werden. Beispiele dafür sind Methyl, Äthyl, Propyl, Isopropyl, Butyl, Pentyl, Hexyl und deren Isomeren. Ein durch das Symbol R dargestelltes Halogenphenyl ist vorzugsweise Chlorphenyl. Eine durch das Symbol R dargestellte Acylaminophenylgruppe kann aliphatische oder aromatische Acylreste enthalten. Beispiele für solche Gruppen sinl Acetaminophenyl oder Benzoylaminophenyl. Eine Diacylimidophenylgruppe ist beispielsweise die Phthalimidophenylgruppe.



   Die erfindungsgemäss erhältlichen Verbindungen der allgemeinen Formel I zeichnen sich durch eine aussergewöhnliche blutzuckersenkende Aktivität bei oraler Applikation aus. Die Verbindungen haben eine kurze Verweilzeit im Organismus und werden weitgehend unverändert ausgeschieden. Sie können daher als Heilmittel in Form pharmazeutischer Präparate Verwendung finden, welche sie in Mischung mit einem geeigneten pharmazeutischen, organischen oder anorganischen inerten Trägermaterial enthalten.



   Beispiel
10 g   1 -(p-Toluolsulfonyl)-3-(2'-oxocyclohexyl)-ham    stoff werden in 120 ml Natronlauge (1,4 g NaOH) gelöst, mit 3 g Natriumborhydrid (ca. 70%ig) versetzt und 15 Stunden bei 200 gerührt. Die Reaktionslösung wird vorsichtig mit verdünnter Essigsäure angesäuert. Der Niederschlag wird abfiltriert und aus Äthanol/Wasser umkristallisiert. Man erhält   1 -(p-Toluolsulfonyl)-3-(2'-hydroxycy-    clohexyl)-harnstoff.

 

   PATENTANSPRUCH



   Verfahren zur Herstellung von   Sulfonylharnstoffderi-    vaten der Formel
T
EMI1.2     
 in der R Phenyl, das durch Halogen, Niederalkyl-, Niederalkoxy-, Niederalkylthio-, Acetyl-, Amino-, Acylamino oder Diacylimidogruppen substituiert sein kann, und n die Zahl 3 oder 4 bedeutet, dadurch gekennzeichnet, dass man ein entsprechendes   o-Oxo-cyclopentyl-bzw.    -cyclohexyl-Derivat reduziert.



   UNTERANSPRÜCHE
1. Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man   1-(p-Toluolsulfonyl)-3-(2'-oxocyclohe-    xyl)-harnstoff reduziert.



   2. Verfahren nach Patentanspruch und Unteranspruch 1, dadurch gekennzeichnet, dass man mittels Natriumborhydrid reduziert.

**WARNUNG** Ende DESC Feld konnte Anfang CLMS uberlappen**.



   



  
 



  Process for the preparation of sulfonamides
The present invention relates to a process for the preparation of sulfonylurea derivatives of the formula I.
EMI1.1
 in which R is phenyl, which may be substituted by halogen, lower alkyl, lower alkoxy, lower alkylthio, acetyl, amino, acylamino or diacylimido groups, and n is the number 3 or 4.



   The inventive method is characterized in that a corresponding o-oxo-cyclopentylbzw. -cyclohexyl derivative reduced.



   The reduction according to the invention can e.g. by treatment with a complex metal hydride such as sodium borohydride.



   Lower alkyl groups contained in radicals represented by the symbol R are to be understood as meaning straight-chain or branched alkyl groups with 1-6 carbon atoms. Examples are methyl, ethyl, propyl, isopropyl, butyl, pentyl, hexyl and their isomers. Halophenyl represented by the symbol R is preferably chlorophenyl. An acylaminophenyl group represented by the symbol R may contain aliphatic or aromatic acyl groups. Examples of such groups are acetaminophenyl or benzoylaminophenyl. A diacylimidophenyl group is, for example, the phthalimidophenyl group.



   The compounds of general formula I obtainable according to the invention are distinguished by an exceptional blood sugar-lowering activity when administered orally. The compounds have a short residence time in the organism and are excreted largely unchanged. They can therefore be used as medicaments in the form of pharmaceutical preparations which they contain as a mixture with a suitable pharmaceutical, organic or inorganic inert carrier material.



   example
10 g of 1 - (p-toluenesulfonyl) -3- (2'-oxocyclohexyl) -ham material are dissolved in 120 ml of sodium hydroxide solution (1.4 g of NaOH), 3 g of sodium borohydride (about 70%) are added and the mixture is carried out for 15 hours stirred at 200. The reaction solution is carefully acidified with dilute acetic acid. The precipitate is filtered off and recrystallized from ethanol / water. 1 - (p-Toluenesulfonyl) -3- (2'-hydroxycyclohexyl) urea is obtained.

 

   PATENT CLAIM



   Process for the preparation of sulfonylurea derivatives of the formula
T
EMI1.2
 in which R is phenyl, which can be substituted by halogen, lower alkyl, lower alkoxy, lower alkylthio, acetyl, amino, acylamino or diacylimido groups, and n is the number 3 or 4, characterized in that a corresponding o-oxo -cyclopentyl- or. -cyclohexyl derivative reduced.



   SUBCLAIMS
1. The method according to claim, characterized in that 1- (p-toluenesulfonyl) -3- (2'-oxocyclohexyl) urea is reduced.



   2. The method according to claim and dependent claim 1, characterized in that one reduces by means of sodium borohydride.

** WARNING ** End of DESC field could overlap beginning of CLMS **.

Claims (1)

**WARNUNG** Anfang CLMS Feld konnte Ende DESC uberlappen **. ** WARNING ** Beginning of CLMS field could overlap end of DESC **. Verfahren zur Herstellung von Sulfonamiden Die vorliegende Erfindung betrifft ein Verfahren zur Herstellung von Sulfonylharnstoffderivaten der Formel I EMI1.1 in der R Phenyl, das durch Halogen, Niederalkyl-, Niederalkoxy-, Niederalkylthio-, Acetyl-, Amino-, Acylaminooder Diacylimidogruppen substituiert sein kann, und n die Zahl 3 oder 4 bedeutet. Process for the preparation of sulfonamides The present invention relates to a process for the preparation of sulfonylurea derivatives of the formula I. EMI1.1 in which R is phenyl, which may be substituted by halogen, lower alkyl, lower alkoxy, lower alkylthio, acetyl, amino, acylamino or diacylimido groups, and n is the number 3 or 4. Das erfindungsgemässe Verfahren ist dadurch gekennzeichnet, dass man ein entsprechendes o-Oxo-cyclopentylbzw. -cyclohexyl-Derivat reduziert. The inventive method is characterized in that a corresponding o-oxo-cyclopentylbzw. -cyclohexyl derivative reduced. Die erfindungsgemässe Reduktion kann z.B. durch Behandlung mit einem komplexen Metalhydrid, wie Natriumborhydrid, bewerkstelligt werden. The reduction according to the invention can e.g. by treatment with a complex metal hydride such as sodium borohydride. Unter niederen Alkylgruppen, die in durch das Symbol R repräsentierten Resten enthalten sind, sollen geradkettige oder verzweigte Alkylgruppen mitl -6 Kohlenstoff- atomen verstanden werden. Beispiele dafür sind Methyl, Äthyl, Propyl, Isopropyl, Butyl, Pentyl, Hexyl und deren Isomeren. Ein durch das Symbol R dargestelltes Halogenphenyl ist vorzugsweise Chlorphenyl. Eine durch das Symbol R dargestellte Acylaminophenylgruppe kann aliphatische oder aromatische Acylreste enthalten. Beispiele für solche Gruppen sinl Acetaminophenyl oder Benzoylaminophenyl. Eine Diacylimidophenylgruppe ist beispielsweise die Phthalimidophenylgruppe. Lower alkyl groups contained in radicals represented by the symbol R are to be understood as meaning straight-chain or branched alkyl groups with 1-6 carbon atoms. Examples are methyl, ethyl, propyl, isopropyl, butyl, pentyl, hexyl and their isomers. Halophenyl represented by the symbol R is preferably chlorophenyl. An acylaminophenyl group represented by the symbol R may contain aliphatic or aromatic acyl groups. Examples of such groups are acetaminophenyl or benzoylaminophenyl. A diacylimidophenyl group is, for example, the phthalimidophenyl group. Die erfindungsgemäss erhältlichen Verbindungen der allgemeinen Formel I zeichnen sich durch eine aussergewöhnliche blutzuckersenkende Aktivität bei oraler Applikation aus. Die Verbindungen haben eine kurze Verweilzeit im Organismus und werden weitgehend unverändert ausgeschieden. Sie können daher als Heilmittel in Form pharmazeutischer Präparate Verwendung finden, welche sie in Mischung mit einem geeigneten pharmazeutischen, organischen oder anorganischen inerten Trägermaterial enthalten. The compounds of general formula I obtainable according to the invention are distinguished by an exceptional blood sugar-lowering activity when administered orally. The compounds have a short residence time in the organism and are excreted largely unchanged. They can therefore be used as medicaments in the form of pharmaceutical preparations which they contain as a mixture with a suitable pharmaceutical, organic or inorganic inert carrier material. Beispiel 10 g 1 -(p-Toluolsulfonyl)-3-(2'-oxocyclohexyl)-ham stoff werden in 120 ml Natronlauge (1,4 g NaOH) gelöst, mit 3 g Natriumborhydrid (ca. 70%ig) versetzt und 15 Stunden bei 200 gerührt. Die Reaktionslösung wird vorsichtig mit verdünnter Essigsäure angesäuert. Der Niederschlag wird abfiltriert und aus Äthanol/Wasser umkristallisiert. Man erhält 1 -(p-Toluolsulfonyl)-3-(2'-hydroxycy- clohexyl)-harnstoff. example 10 g of 1 - (p-toluenesulfonyl) -3- (2'-oxocyclohexyl) -ham material are dissolved in 120 ml of sodium hydroxide solution (1.4 g of NaOH), 3 g of sodium borohydride (about 70%) are added and the mixture is carried out for 15 hours stirred at 200. The reaction solution is carefully acidified with dilute acetic acid. The precipitate is filtered off and recrystallized from ethanol / water. 1 - (p-Toluenesulfonyl) -3- (2'-hydroxycyclohexyl) urea is obtained. PATENTANSPRUCH PATENT CLAIM Verfahren zur Herstellung von Sulfonylharnstoffderi- vaten der Formel T EMI1.2 in der R Phenyl, das durch Halogen, Niederalkyl-, Niederalkoxy-, Niederalkylthio-, Acetyl-, Amino-, Acylamino oder Diacylimidogruppen substituiert sein kann, und n die Zahl 3 oder 4 bedeutet, dadurch gekennzeichnet, dass man ein entsprechendes o-Oxo-cyclopentyl-bzw. -cyclohexyl-Derivat reduziert. Process for the preparation of sulfonylurea derivatives of the formula T EMI1.2 in which R is phenyl, which can be substituted by halogen, lower alkyl, lower alkoxy, lower alkylthio, acetyl, amino, acylamino or diacylimido groups, and n is the number 3 or 4, characterized in that a corresponding o-oxo -cyclopentyl- or. -cyclohexyl derivative reduced. UNTERANSPRÜCHE 1. Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man 1-(p-Toluolsulfonyl)-3-(2'-oxocyclohe- xyl)-harnstoff reduziert. SUBCLAIMS 1. The method according to claim, characterized in that 1- (p-toluenesulfonyl) -3- (2'-oxocyclohexyl) urea is reduced. 2. Verfahren nach Patentanspruch und Unteranspruch 1, dadurch gekennzeichnet, dass man mittels Natriumborhydrid reduziert. 2. The method according to claim and dependent claim 1, characterized in that one reduces by means of sodium borohydride.
CH787469A 1966-08-08 1966-08-08 Sulphonamides and process for the manufacture thereof CH509991A (en)

Priority Applications (18)

Application Number Priority Date Filing Date Title
CH787469A CH509991A (en) 1966-08-08 1966-08-08 Sulphonamides and process for the manufacture thereof
CH787169A CH510647A (en) 1966-08-08 1966-08-08 Sulphonamides and process for the manufacture thereof
CH787569A CH509992A (en) 1966-08-08 1966-08-08 Process for the preparation of sulfonamides
CH787269A CH510648A (en) 1966-08-08 1966-08-08 Sulphonamides and process for the manufacture thereof
CH787369A CH509990A (en) 1966-08-08 1967-07-07 Sulphonamides and process for the manufacture thereof
SE10481/67A SE334354B (en) 1966-08-08 1967-07-12
IL28401A IL28401A (en) 1966-08-08 1967-07-26 Arylsulfonyl ureas,their manufacture and pharmaceutical compositions containing them
DE1967H0063446 DE1668199B2 (en) 1966-08-08 1967-07-29 BENZOLSULFONYL-3- (2-HYDROXYCYCLOHEXYL) UREA
NL6710676A NL6710676A (en) 1966-08-08 1967-08-02
BE702280D BE702280A (en) 1966-08-08 1967-08-04
GB50520/68A GB1147404A (en) 1966-08-08 1967-08-04 Novel sulphonamide derivatives
GB50521/68A GB1147405A (en) 1966-08-08 1967-08-04 Novel oxazolidinone derivatives
GB35845/67A GB1147403A (en) 1966-08-08 1967-08-04 Sulphonamides
ES343910A ES343910A1 (en) 1966-08-08 1967-08-07 Sulphonamides
DK401867AA DK122761B (en) 1966-08-08 1967-08-07 Analogous process for the preparation of arylsulfonylurea derivatives.
JP5054967A JPS5516575B1 (en) 1966-08-08 1967-08-08
FR117194A FR1546595A (en) 1966-08-08 1967-08-08 Process for the preparation of sulfonamides
FR117192A FR7148M (en) 1966-08-08 1967-08-08

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
CH1136566A CH500176A (en) 1966-08-08 1966-08-08 Sulphonamides and process for the manufacture thereof
CH787469A CH509991A (en) 1966-08-08 1966-08-08 Sulphonamides and process for the manufacture thereof
CH787569A CH509992A (en) 1966-08-08 1966-08-08 Process for the preparation of sulfonamides

Publications (1)

Publication Number Publication Date
CH509991A true CH509991A (en) 1971-07-15

Family

ID=27175874

Family Applications (2)

Application Number Title Priority Date Filing Date
CH787469A CH509991A (en) 1966-08-08 1966-08-08 Sulphonamides and process for the manufacture thereof
CH787569A CH509992A (en) 1966-08-08 1966-08-08 Process for the preparation of sulfonamides

Family Applications After (1)

Application Number Title Priority Date Filing Date
CH787569A CH509992A (en) 1966-08-08 1966-08-08 Process for the preparation of sulfonamides

Country Status (11)

Country Link
JP (1) JPS5516575B1 (en)
BE (1) BE702280A (en)
CH (2) CH509991A (en)
DE (1) DE1668199B2 (en)
DK (1) DK122761B (en)
ES (1) ES343910A1 (en)
FR (1) FR7148M (en)
GB (3) GB1147404A (en)
IL (1) IL28401A (en)
NL (1) NL6710676A (en)
SE (1) SE334354B (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
MD3259253T2 (en) 2015-02-16 2020-06-30 Univ Queensland Sulfonylureas and related compounds and use of same
JP7072586B2 (en) 2017-05-24 2022-05-20 ザ ユニバーシティ オブ クィーンズランド New compounds and uses
TWI789401B (en) 2017-07-07 2023-01-11 愛爾蘭商英弗雷佐姆有限公司 Novel compounds

Also Published As

Publication number Publication date
ES343910A1 (en) 1968-10-01
GB1147405A (en) 1969-04-02
DE1668199A1 (en) 1971-09-02
NL6710676A (en) 1968-02-09
GB1147403A (en) 1969-04-02
IL28401A (en) 1971-04-28
FR7148M (en) 1969-08-04
SE334354B (en) 1971-04-26
JPS5516575B1 (en) 1980-05-02
DE1668199B2 (en) 1976-06-24
DK122761B (en) 1972-04-10
BE702280A (en) 1968-02-05
CH509992A (en) 1971-07-15
GB1147404A (en) 1969-04-02

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