US3725430A - DERIVATIVES OF p-AMINOALKYL BENZENESULFONAMIDES - Google Patents

DERIVATIVES OF p-AMINOALKYL BENZENESULFONAMIDES Download PDF

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US3725430A
US3725430A US00061510A US3725430DA US3725430A US 3725430 A US3725430 A US 3725430A US 00061510 A US00061510 A US 00061510A US 3725430D A US3725430D A US 3725430DA US 3725430 A US3725430 A US 3725430A
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imino
phenylsulphonyl
imidazolidine
ethyl
aminoethyl
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H Dietrich
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Novartis Corp
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Ciba Geigy Corp
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole 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
    • C07D233/44—Nitrogen atoms not forming part of a nitro radical
    • C07D233/46—Nitrogen atoms not forming part of a nitro radical with only hydrogen atoms attached to said nitrogen atoms

Definitions

  • the present invention relates to new derivatives ofpaminoalkyl benzenesulfonamides, processes for their preparation, to medicaments containing'the new compounds and their use.
  • the present invention concerns compounds of the formula I,
  • R is alkyl having oneito six carbon atoms, allyl, cycloalkyl having five to eight carbon atoms, or cycloalkenyl having five to eight carbon atoms;
  • R is hydrogen, ethyl or methyl;
  • R can denote cyclopentyl, which can be optionally substituted by alkyl having one-three carbon atoms; cyclohexyl, which can besubstituted by ethyl or methyl; cycloheptyl, optionally substituted by methyl; as well ascyclooctyl; as cycloalkenyl, R, can denote-2-cyclopenten-l yl, 2-cyclohexen-lyl, 3-cyclohexen l yl, 2-methyl-2-cyclohexen l-yl, 3--
  • the substituent R embraces the'same alkyl, cycloal-- kyl or cycloalkenyl group'skas stated'under' R asalkenyl, R can denoteallyLfl -methylallyl,2-methylallyl,2 or 3-butenyl, or 2-, '3- or 4-pentenyl.
  • Suitable as reactive derivatives of a carbarnic acid or thioca'rbamic acid of formula III are, e.g. the halides,
  • the chlorides especially the lower alkyl esters, particularly'the methyl or ethyl esters, the phenyl esters, the amides, the lower monoor dialkylamides, in particular the N-methyl amides and the N,N-dirnethylamides, the diphenylamides, also the N-acylamides such as, e.g. the
  • the reaction is performed, e.g. at room temperature, or by heating in'an inert organic solvent.
  • Suitable as such are, e.g. hydrocarbons such as benzene, toluene or xylene, ethers such as diethyl ether, dioxane or tetrahydrofuran, chlorinated hydrocarbons such as ;-methylene chloride, and lower ketones such as acetone or methyl ethyl ketone.
  • the reaction can, in general, be
  • such agents e.g. alkali metal alcoholates and alkali metal hydroxides, can beadded.
  • inorganic bases or salts such as, e.g. an alkali hydroxide, alkali acetate, alkali hydrogen carbonate, alkali carbonate and alkali phosphate, such assodium hydroxide,.sodium acetate,
  • organic bases are also suitable such as, e.g. pyridine, trimethylor triethylamine, diisopropylamine,
  • N-alkali metal derivatives of these compounds such as e.g. sodium
  • Thestarting compounds of formula II are, for their part, new compounds. They can beproduced, e.g. by
  • Suitable reactive derivatives of a sulfonic acid of formula V are halides, especially chlorides and anhydrides of formula Va,
  • starting materials of formula II are obtained by reacting substituted p-(aminoalkyl)- benzenesulfonamides of formula VII,
  • the preparation of the starting compounds of formula III and of formula IV is carried out using the generally known preparationmethods for isocyanates, and carbamic acid derivatives and thiocarbamic acid derivatives, respectively.
  • compositions comprised by the present invention are readily available by allowing to reach a compound of formula I with a suitable acid and isolating the salt by conventional methods.
  • physiologically harmless inorganic or organic acids such as, e.g. hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid, methanesulfonic acid, acetic acid, lactic acid, succinic (Vlll acid, tartaric acid and maleic acid.
  • hypoglycemic sulfonyl ureas such as, e.g.
  • p-toluene-sulfonylbutyl urea p-chlorobenzenesulfonylpropyl urea
  • p[2(2- methoxy-S-chlorobenzamido)-ethyI]-phenylsulfonylcyclohexy] urea can be used.
  • the compounds of the present invention have been found to have valuable hypoglycemic activities in warm-blooded animals upon oral or parenteral administration. These activities are illustratively demonstrated in rats by orally administering the test compound to groups of five to six animals which have not been fed for 24 hours. Blood samples are taken from the vein, and the blood sugar content is determined according to the method of Hagedom-Jenson with an auto-analyzer.
  • the compounds of formula I. and the pharmaceutically acceptable salts thereof are preferably administered orally in a daily dosage of from 10 to 400 mg/kg of bodyweight.
  • the dosage must necessarily be adjusted to the age, size and condition of the particular host being treated.
  • the compounds of the invention are provided in dosage unit forms including'for example, tablets, capsules, dragees, powders, syrups, elixits, and the like.
  • Suitable dosage units such as dragees or tablets, preferablycontain 10-200 mg of an active substance according to the invention, whereby the content of ac tive substance is. 20-80 percent by weight.
  • Tablets and dragees are produced by combining the active substance, e.g. with solid pulverulent-carriers such as lactose, saccharose, sorbitolor mannitol; starches such as potato starch, maize starch or amylopectin, also laminaria powder or citrus pulp powder, cellulose derivatives or gelatine, optionally with the addition of lubricants, such as magnesium or calcium stearate or polyethylene glycols of suitable molecular weights.
  • solid pulverulent-carriers such as lactose, saccharose, sorbitolor mannitol
  • starches such as potato starch, maize starch or amylopectin, also laminaria powder or citrus pulp powder, cellulose derivatives or gelatine
  • the tablets and dragee-cores are coated, e.g. with concentrated sugar solutions whichmay also contain, e. g. gum arabic, talcum and/or titanium dioxide; or. with a lacquer dissolved in readily volatile organic solvents or mixtures of solvents.
  • Dyestuffs can be added to these coatings, e.g. to distinguish between varying dosages of active substance.
  • suitablev dosage units for oral administration are hard gelatin Capsules, as well as soft closed capsules made from gelatine and a softener such as glycerin.
  • the hard capsules preferably contain the active substance as a granulate, e.g. in admixture with fillers such as maize starch, and/or lubricants such as talcum or magnesium stearate and, optionally, stabilizers such as sodium metabisulfite (Na S O or ascorbic acid.
  • the active substance is n-propylisocyanate, dissolved or suspended in suitable liquids such as liquid polyethylene glycols, whereby stabilizers may also be added.
  • EXAMPLE 1 a An amount of 39.8 g of l-[p-(2-aminoethyl)-phenyl sulphonyl] -2-imino-3-n-butylimidazolidinedihydrochloride is dissolved in ml of water, and the base liberated with ml of 2-n sodium hydroxide solution. It is extracted with 3 times 250ml of methylene chloride. To the methylene chloride solution (dried with sodium sulphate) are added 8.5 g of npropylisocynate, and stirring is maintained for 1 hour. The reaction mixture is then concentrated in vacuo, and the crystalline residue recrystallized from ethyl acetate.
  • the obtained oil (free base) is DIS- SOLVED in alcohol, and made acidic with saturated alcoholic hydrochloric acid.
  • l-[p-(2-aminoethyl)- phenylsulphonyl]-2-imino-3-butyl-imidazolidine dihydrochloride precipitates, M.P. 23 l-233.
  • EXAMPLE 2 In an analogous manner to Example 1 are obtained: from 38.4 g of 1-[p-(2-amino-ethyl)-phenylsulphonyl]- 2-imino-3-isopropyl-imidazolidine-dihydrochloride and 12.5 g of cyclohexyl-isocyanate the l-[p-(2- (cyclohexyl-ureido)-ethyl)-phenylsulphonyl]-2-imino- 3-isopropyl-imidazolidine, M.P. 158-l 58.
  • EXAMPLE 4 a 38.4 g of 1-[p-(2-aminoethyl)-phenylsulphonyl]- 2-imino-3-n-propyl-imidazolidine dihydrochloride are dissolved in ml of water; and the base is liberated with ml of 2-n sodium hydroxide solution. It is extracted with 3 times 250 ml of methylene chloride. To the methylene chloride solution (dried with sodium sulphate) are added 12.5 g of cyclohexylisocyanate, and stirring is maintained for 1 hour. The reaction mixture is then concentrated in vacuo, and the crystalline residue recrystallized from ethyl acetate.
  • the obtained cloudy solution is rendered alkaline with concentrated sodium hydroxide solution, saturated with sodium chloride, and extracted three times with methylene chloride; the organic phases are dried over sodium sulphate, filtered and concentrated by evaporation.
  • the obtained oil (free base) is dissolved in alcohol, and made acid with saturated alcoholic hydrochloric acid.
  • EXAMPLE 5 a 39.8 g of 1-[p-(2-aminoethyl)-phenylsulphonyl]- 2-imino-3-isobutyl-imidazolidine dihydrochloride are dissolved in 100 ml of water, and the base liberated with 150 ml of 2-n sodium hydroxide solution. It is extracted with 3 times 250 ml of methylene chloride. To the methylene chloride solution (dried with sodium sulphate) are added 8.5 g of n-propylisocyanate, and stirring is maintained for 1 hour. The reaction mixture is then concentrated in vacuo, and the crystalline residue recrystallized from ethyl acetate. The 1-[p-(2- (3 -n-propylureido)-ethy1)-pheny1sulphonyl]-2-imino- 3-isobutyl-imidazolidine melts at 154156.
  • the obtained cloudy solution is made alkaline with concentrated sodium hydroxide solution, saturated with sodium chloride, and extracted three times with methylene chloride; the organic phases are dried over sodium sulphate, filtered and concentrated by evaporation.
  • the obtained oil (free base) is dissolved in alcohol and made acid with saturated alcoholic hydrochloric acid.
  • EXAMPLE 6 In an analogous manner to Example 4 is obtained, starting with 39.8 g of 1-[p-(2-aminoethyl)-phenylsulphonyl]-2-imino-3-isobutyl-imidazolidinehydrochloride with 12.5 g of cyclohexylisocyanate, 1- [p-( 2-( 3-cyclohexylureido )-ethyl )-phenylsulph0nyl ]-2 -imino-3-isobutyl-imidazolidine, M.P. (from acetyl acetate).
  • EXAMPLE 7 a 41.0 g of 1-[p-(2-aminoethyl)-phenylsulphonyl]- 2-imino-3-cyclopentyl-imidazolidine-dihydrochloride are dissolved in ml of water, and the base is liberated with ml of 2-n sodium hydroxide solution. The base is extracted with 3 times 250 ml of methylene chloride. To the methylene chloride solution (dried with sodium sulphate) are added 5.7 g of methylisocyanate, and stirring is maintained for 1 hour. The reaction mixture is then concentrated in vacuo, and the crystalline residue recrystallized from ethyl acetate. 1- [p-(2-(3-methylureido)-ethyl)-phenylsulphonyl]-2- imino-3-cyclopentyl-imidazolidine melts at l291 30.
  • the obtained cloudy solution is made alkaline with concentrated sodium hydroxide solution, saturated with sodium chloride, and extracted three times with methylene chloride; the organic phases are dried over sodium sulphate, filtered and concentrated by evaporation.
  • the obtained oil (free base) is dissolved in alcohol, and made acid with saturated alcoholic hydrochloric acid.
  • l-[p-(2aminoethyl)- phenylsulphonyl]-2-imino-3-cyc1opentylimidazolidinc-dihydrochloride, M.P. 270, position) precipitates.
  • EXAMPLE 9 a 42.4 g of l-[p-(2-aminoethyl)-phenylsulphonyl]- 2-imino-3-cyclohexyl-imidazolidine-dihydrochloride are dissolved in 100 ml of water, and the base is liberated with 150 ml of 2-n sodium hydroxide solution. The base is extracted with 3 times 250 ml of methylene chloride. To the methylene chloride solution (dried with sodium sulphate) are added 9.9 g of n-butylisocyanate, and stirring is maintained for one hour. The reaction mixture is thenconcentrated in vacuo, and the crystalline residue recrystallized from ethyl acetate.
  • the base is liberated with 150 ml of 2-n sodium hydroxethyl acetate.
  • the obtained oil (free base) is dissolved in a1- cohol, and made acid with saturated alcoholic hydrochloric acid.
  • imidazolidine is dissolved in 370 ml of 2-n hydrochloric acid, and the solution refluxed for 6 hours. The solution is then concentrated to dryness in vacuo, and the obtained oil dissolved in alcohol.
  • EXAMPLE 12 the base is liberated with 150 ml of 2-n sodium hydroxide solution.
  • the base is extracted with 3 times 250 ml of methylene chloride.
  • To the methylene chloride solution (dried with sodium sulphate) are added 8.5 g of npropylisocyanate, and stirring is maintained for one hour.
  • the reaction mixture is thereupon concentrated in vacuo, and the crystalline residue recrystallized from ethyl acetate.
  • the l-[p-(2-(3-n-propylureido)-ethyl phenylsulphonyl]-2-imino-3-n-butyl-4-methylimidazolidine melts at l09l 12.
  • EXAMPLE 15 Starting with 41.1 g of l-[p-(2-aminoethyl)-phenylsulphonyl]-2-imino-3-n-butyl-4-methyl*imidazolidinedihydrochloride are obtained, analogously to Example 14, with 12.5 g of cyclohexylisocyanate, the l-[p-(2-(3- cyclohexylureido)-et hyl)-phenyl-sulphonyl]-2-irnino- 3-n-butyl-4-methyl-imidazolidine, M.P. 137138 (from ethyl acetate).
  • EXAMPLE 17 39.7 g of l-[p-(2-aminoethyl)-phenylsulphonyl]-2- imino-3-n-propyl-5-methyl-imidazolidine-dihydrochloric are dissolved in 100 ml of water,v and the base is liberated with 150 m1 of 2-n sodium hydroxide solution. The base is extracted with 3 times 250 ml of methylene chloride. To the methylene chloride solution (dried with sodium sulphate) are added 11.] g of cyclopentylisocyanate, and stirring is maintained for one hour. The reaction mixture is thereupon concentrated in vacuo, and the crystalline.
  • EXAMPLE 19 a 39.8 g of l-[p-(2-aminoethyl)-phenylsulphonyl]- 2-imino-3-n-butyl-irnidazolidine-dihydrochloride are dissolved in ml of water, and the base is liberated with ml of 2-n sodium hydroxide solution. It is extracted with 3 times 250 ml of methylene chloride. T o the methylene chloride solution (dried with sodium sulphate) are added 14 g of 4-cyclohex-3-enylisothiocyanate, and stirring is maintained for 1 hour.
  • the reaction'mixture is thereupon concentrated in vacuo, and the crystalline residue recrystallized from ethyl acetate.
  • EXAMPLE 20 39.8 g of l[p-(2-aminoethyl)-phenylsulphony1]-2- imino-3-isobutyl-imidazolidine-dihydrochloride are dissolved in 100 m1 of water, and the base is liberated with 150 ml of 2-n sodium hydroxide solution. It is extracted with 3 times 250 ml of methylene chloride. To the methylene chloride solution (dried with sodium sulphate) are added 9.9 g of n-butylisocyanate, and stirring is maintained for 1 hour. The reaction mixture is thereupon concentrated in vacuo, and the crystalline residue recrystallized from ethyl acetate.
  • EXAMPLE 21 a 4L0 g of l-[p-(2-aminoethyl)-phenylsulphonyl]- 2-imino-3-cyclopentyl-imidazolidine-dihydrochloride are dissolved in 100 ml of water, and the base is liberated with 150 ml of 2-n sodium hydroxide solution. It is extracted with 3 times 250 ml of methylene chloride. To the methylene chloride solution (dried with sodium sulphate) are added 14.1 g of cyclohexylisothiocyanate, and stirring is maintained for 1 hour. The reaction mixture is thereupon concentrated in vacuo, and the crystalline residue recrystallized from ethyl acetate.
  • EXAMPLE 22 a 42.4 g of l-[p-(2-aminoethyl)-phenylsulphonyl]- 2-imino-3-cyclohexyl-imidazolidine-dihydrochloride are dissolved in 100 ml of water, and the base is liberated with 150 ml of 2-n sodium hydroxide solution. It is extracted with 3 times- 250 ml of-methylene chloride. To the methylene chloride solution, (dried with sodium sulphate) are added 12.7 g of cyclopentylisothiocyanate, and stirring is maintained for one hour.
  • the reaction mixture is thereupon concentrated in vacuo, and the crystalline residue recrystallized from ethyl acetate.
  • EXAMPLE 23 EXAMPLE 24 a. 39.8 g of l-[p-(2-aminoethyl)-phenylsulphonyl]- 2-imino-3-n-butyl-imidazolidine-dihydrochloride are dissolved in 100 ml of water, and the base is liberated tracted twice with ml of methylene chloride.
  • EXAMPLE 25 a 39.8 g of l [p-(2-aminoethyl)-phenylsulphonyl]-2- imino-3-n-butyl-imidazolidine-dihydrochloride are dissolved in 100 ml of water, and the base is liberated with ml of 2-n sodium hydroxide solution. The base is extracted with 3 times 250 ml of methylene chloride. To the methylene chloride solution (dried with sodium sulphate) are added 20 g of triethylarnine. At room temperature is then added dropwise the solution of 14.8 g.
  • EXAMPLE 26 a 39.8 g of 1-[p-(2-aminoethyl)-phenylsulphonyl]- 2-imino-3-isobutyl-imidazolidine dihydrochloride are dissolved in 100 ml of water, and the base is liberated with 150 ml of 2-n sodium hydroxide solution. The base is extracted with 3 times 250 ml of methylene chloride. To the methylene chloride solution (dried with sodium sulphate) are added 20 g of triethylamine.
  • EXAMPLE 27 Analogously to Example 28 are obtained: from 39.6 g of l-[p-(Z-amino-ethyl)-phenylsulphonyll- 2-imino-3-n-butyl-imidazolidine-dihydrochloride and 15.0 g of 4-morpholinecar-bonylchloride the 1-[p-(2- (4-morpholinecarboxamido) ethyl)-phenylsulphonyl]- 2-imino-3-n-butyl-imidazolidine, M.P. 176 177.
  • EXAMPLE 2s a. 41.0 g of 1-[p-(2-aminoethyl)-phenylsulphonyl]- 2-imino-3-cyclopentyl-imidazolidine-dihydrochloride are dissolved in 100 ml of water, and thebase is liberated with 150 ml of 2-n sodium hydroxide solution. The base is extracted with 3 times 250 ml of methylene chloride.
  • EXAMPLE 29 39.7 g of 1-[p-(2-aminoethyl)-phenylsulphonyl]-2- imino-3-n-butyl-imidazolidine-dihydrochloride are dissolved in 100 ml of water, and the base is liberated with 150 ml of 2-n sodium hydroxide solution. The base is extracted with 3 times 250 ml of methylene chloride. To the methylene chloride solution (dried with sodium sulphate) are added 20 g of triethylamine. At room temperature is then added the solution of 15 g of 4- morpholinyl chloride in 100 ml of methylene chloride,
  • EXAMPLE 30 1,000 g of l-[p-(2( 3-butylureido)-ethy1)-pheny1 sulphonyl]-2-imino-3-cyc1ohexyl-imidazolidine are mixed with 500 g of lactose and 270 g of potato starch; the mixture is then moistened with an aqueous solution of 8.0 g of gelatine, and granulated through a sieve.
  • the tablets may be provided with grooves for more precise adjustment of the dosage amount
  • EXAMPLE 32 A granulate is prepared from 1,000 g of l-[p-(2-(3- buty1-thio-ureido)-ethyl)-phenyl-sulphonyl]-2-imino- 3-cyclohexyl-imidazolidine, 345.0 g of lactose and the aqueous solution of 6.0 g of gelatine. After drying, the granulate is mixed with 10.0 g of colloidal silicon dioxide, 40.0 g of talcum, 40.0 g of potato starch and 5.0 g
  • R is alkyl of one to six carbon atoms, allyl, cycloalkyl of five to eight carbon atoms or cycloalkenyl of five to eight carbon atoms;
  • R is hydrogen, ethyl or methyl
  • R is alkyl of one to six carbon atoms, cycloalkyl of at most eight carbon atoms, cycloalkenyl of at most eight carbon atoms, alkenyl of three to five carbon atoms or phenyl;
  • R is hydrogen, alkyl of one to six carbon atoms or phenyl
  • R and R together are a polymethylene chain of four to seven carbon atoms or morpholino;
  • X is oxygen or sulfur
  • n 2 or 3; or a pharmaceutically acceptable acid addition salt thereof.
  • a compound according to claim 1 which is l-[p- 2-( 3-n-butyl-2-thioureido )-ethyl )-phenylsulfonyl ]-2 imino-3-n-butyl-imidazolidine.
  • a compound according to claim 1 which is l-[p- (2 3-n-butylureido )-ethyl)-phenylsulfonyl ]-2-imino- 3-cyclohexyl-imidazolidine.
  • a compound according to claim 1 which is l-[p- 2-( 3-n-propylureido)-ethyl )-phenylsu]fonyl ]-2-imino- 3 4-methylcyclohexyl )-irnidazolidine.
  • a compound according to claim 1 which is l-[p- 2-( 3 -ethyl-2-thioureido )-ethyl )-phenylsulfonyl ]-2- imino-3-cyclopentylimidazolidine.

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  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
US00061510A 1969-08-08 1970-08-05 DERIVATIVES OF p-AMINOALKYL BENZENESULFONAMIDES Expired - Lifetime US3725430A (en)

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CH1208569A CH513874A (de) 1969-08-08 1969-08-08 Verfahren zur Herstellung von neuen Derivaten des p-(Aminoalkyl)-benzolsulfonamids

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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1046174A (en) * 1964-04-20 1966-10-19 Bayer Ag Process for the production of n,n'-disulphonyl-1,3-diazacylco alkanes
US3538085A (en) * 1966-03-24 1970-11-03 Geigy Chem Corp 1-phenylsulfonyl-2-imino-imidazolidines and hexahydropyrimidines

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1052113A (enrdf_load_html_response) * 1963-02-07
CH505829A (de) * 1968-03-14 1971-04-15 Ciba Geigy Ag Verfahren zur Herstellung von neuen Derivaten des p-Aminoalkylbenzolsulfonamids

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1046174A (en) * 1964-04-20 1966-10-19 Bayer Ag Process for the production of n,n'-disulphonyl-1,3-diazacylco alkanes
US3538085A (en) * 1966-03-24 1970-11-03 Geigy Chem Corp 1-phenylsulfonyl-2-imino-imidazolidines and hexahydropyrimidines

Non-Patent Citations (6)

* Cited by examiner, † Cited by third party
Title
Dietrich Chem. Abst. Vol. 70, No. 47450g (1969). QD1.A51 *
Dietrich Chem. Abst. Vol. 71, No. 91476q (1969). QD1.A51 *
Dietrich Chem. Abst. Vol. 72, No. 12728t (1970). QD1.A51 *
Dietrich Chem. Abst. Vol. 72, No. 31793b (1970). QD1.A51 *
Schotte et al. Chem. Abst. Col. 22, pages 1759 1760 (1928). QD1.A51 *
Yoshitomi Pharmaceutical Industries Chem. Abst. Vol. 62, column 16135 (1965) QD1.A51 *

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ZA705468B (en) 1971-04-28
SE367408B (enrdf_load_html_response) 1974-05-27
FI52461C (fi) 1977-09-12
IE34445B1 (en) 1975-05-14
DK125854B (da) 1973-05-14
FR2068476B1 (enrdf_load_html_response) 1973-12-21
CH518287A (de) 1972-01-31
DE2039419A1 (de) 1971-02-18
NL167423C (nl) 1981-12-16
DE2039419B2 (de) 1978-01-05
NO124373B (enrdf_load_html_response) 1972-04-10
PL80964B1 (enrdf_load_html_response) 1975-08-30
BG17544A3 (bg) 1973-11-10
CA925089A (en) 1973-04-24
IL35080A (en) 1973-11-28
NL7011391A (enrdf_load_html_response) 1971-02-10
ES382540A1 (es) 1972-12-01
AT303750B (de) 1972-12-11
DE2039419C3 (de) 1978-09-14
GB1313578A (en) 1973-04-11
CH513874A (de) 1971-10-15
BG17961A3 (bg) 1974-03-05
NL167423B (nl) 1981-07-16
BE754597A (fr) 1971-02-08
IE34445L (en) 1971-02-08
IL35080A0 (en) 1970-10-30

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