DE1445006A1 - 3,4-dihydro-1,2,4-benzothiadiazine-1,1-dioxyde - Google Patents
3,4-dihydro-1,2,4-benzothiadiazine-1,1-dioxydeInfo
- Publication number
- DE1445006A1 DE1445006A1 DE19591445006 DE1445006A DE1445006A1 DE 1445006 A1 DE1445006 A1 DE 1445006A1 DE 19591445006 DE19591445006 DE 19591445006 DE 1445006 A DE1445006 A DE 1445006A DE 1445006 A1 DE1445006 A1 DE 1445006A1
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- general formula
- methyl
- benzothiadiazine
- dihydro
- salts
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/15—Six-membered rings
- C07D285/16—Thiadiazines; Hydrogenated thiadiazines
- C07D285/18—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines
- C07D285/20—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines condensed with carbocyclic rings or ring systems
- C07D285/22—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D285/24—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with oxygen atoms directly attached to the ring sulfur atom
- C07D285/26—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with oxygen atoms directly attached to the ring sulfur atom substituted in position 6 or 7 by sulfamoyl or substituted sulfamoyl radicals
- C07D285/28—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with oxygen atoms directly attached to the ring sulfur atom substituted in position 6 or 7 by sulfamoyl or substituted sulfamoyl radicals with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/15—Six-membered rings
- C07D285/16—Thiadiazines; Hydrogenated thiadiazines
- C07D285/18—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines
- C07D285/20—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines condensed with carbocyclic rings or ring systems
- C07D285/22—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D285/24—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with oxygen atoms directly attached to the ring sulfur atom
- C07D285/26—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with oxygen atoms directly attached to the ring sulfur atom substituted in position 6 or 7 by sulfamoyl or substituted sulfamoyl radicals
- C07D285/30—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with oxygen atoms directly attached to the ring sulfur atom substituted in position 6 or 7 by sulfamoyl or substituted sulfamoyl radicals with hydrocarbon radicals, substituted by hetero atoms, attached in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
3, 4-Dihydro-1, 2, 4-benzothiadiazin-1, l-dioxyde. 3, 4-dihydro-1, 2, 4-benzothiadiazine-1, l-dioxyde.
Gegenstand des Patentes Nr.. (DAS 1 112 079) ist die Herstellung von 3, 4-Dihydro-1, 2, 4-benzothiadaizin-1,1-dixoyden der allgemeinen Formel worin R1, R3 und R5 Wasserstoffatome, Alkyl-oder Acylreste bedeuten, R2 für ein Wasserstoffatom, eine Alkyl-, vinyl-, , Aryl- oder-Aralkylgruppe oder einen heterocyclischen Rest, der auch kber einen Alkylrest an den Thiadiazinring gebunden sein kann, steht, wobei die Alkylgruppe eine Hydroxy-, Alkoxy-oder Dialkylaminogruppe oder ein Halogenatom tragen kann und Arylgruppen und heterocyclische Reste durch Alkyl-, Hydroxy-, Alkoxy-, Mercapto- oder Alkylmercapto-, Dialkylamino-oder Sulfamylgruppen oder Halogenatome substituiert sein können, und R4 ein Halogenatom, einen Alkylrest oder eine verätherte Hydroxygruppe darstellt, und Salzen dieser verbindungen, ausgenommen 6-Chlor-7-sulfamyl-3,4-dihydro-1,2,4-benzothiadiazin-1,1-dioxyd ; sie werden erhalten, wenn man entweder a) eine 2-Sulfamyl-ariilinverbindung der allgemeinen Formel worin R1, und R3 fur Wasserstoffatome oder Alkylreste stehen, oder deren Salze mit einem Aldehyd der Formel R2-GHO umsetzt oder b) ein 1, 2,4-Benzothiadiazin-1,1-dioxyd der allgemeinen Formel mit einem Alkalimetallborhydrid hydriert oder elektrolytisch reduziert und gegebenenfalls anschliessend erhaltene Verbindungen, in denen R1, R3 und/oder R5 Wasserstoffatome darstellen, in an sich bekannter Weise alkyliert oder acyliert und/oder erhaltene Salze in die freien Verbindungen oder erhaltene freie Verbindungen in ihre Salze überfuhrt.The subject of patent no. (DAS 1 112 079) is the preparation of 3, 4-dihydro-1, 2, 4-benzothiadaizin-1,1-dixoyd of the general formula where R1, R3 and R5 represent hydrogen atoms, alkyl or acyl radicals, R2 represents a hydrogen atom, an alkyl, vinyl, aryl or aralkyl group or a heterocyclic radical which can also be bonded to the thiadiazine ring via an alkyl radical , where the alkyl group can carry a hydroxy, alkoxy or dialkylamino group or a halogen atom and aryl groups and heterocyclic radicals can be substituted by alkyl, hydroxy, alkoxy, mercapto or alkylmercapto, dialkylamino or sulfamyl groups or halogen atoms, and R4 represents a halogen atom, an alkyl radical or an etherified hydroxyl group, and salts of these compounds, with the exception of 6-chloro-7-sulfamyl-3,4-dihydro-1,2,4-benzothiadiazine-1,1-dioxide; they are obtained when either a) a 2-sulfamyl-ariline compound of the general formula in which R1 and R3 represent hydrogen atoms or alkyl radicals, or reacts their salts with an aldehyde of the formula R2-GHO or b) a 1,2,4-benzothiadiazine-1,1-dioxide of the general formula hydrogenated or electrolytically reduced with an alkali metal borohydride and optionally subsequently obtained compounds in which R1, R3 and / or R5 represent hydrogen atoms, alkylated or acylated in a manner known per se and / or salts obtained into the free compounds or obtained free compounds converted into their salts .
Es wurde nun gefunden, dass Verbindungen der angegebenen Formel, worin R1 fkr eine Methylgruppe steht, R5 ein Wasserstoffatom oder die Methylgruppe bedeutet, R4 ein Chloratom darstellt, R3 ur ein Wasserstoffatom und R2 für eine Methyl-., Butyl-oder Benzylgruppe stehle und ihre Salze ebenfalls die wertvolle diuretische ur, d natriuretische Wirksamkeit besitzen. It has now been found that compounds of the formula given where R1 stands for a methyl group, R5 a hydrogen atom or the methyl group means, R4 represents a chlorine atom, R3 represents a hydrogen atom and R2 represents one Methyl, butyl or benzyl groups and their salts are also valuable diuretic ur, d have natriuretic activity.
Die Erfindung betrifft daher 3,4-Dihydro-1,2,4-benzothiadiazin-l, l-dioxyde der allgemeinen Formel 1 in der R2 eine Methyl-, Betyl- eder BEnzylgruppe und R5 ein Wasserstoffatom oder eine Methylgruppe bedeutet. und Salze dieser Verbindungen. Sie werden gemäss Patent (DAS 1 112 079) erhalten, wenn man entweier a) eine Sulfamylanilinverbindung der allgemeinen Formel II in der R5 die oben angegebene Beduetung hat, doer deren Salze mit einem Aldehyd der allgemeinen Ferne R2-CHO, in der R2 die oben angegebene Bedestung hat, umsetzt oder b) ein 3,4-Dihydro-1,2,4-benzothiadiazin-1,1-dioxydderivat der allgemeinen Formel III in der R2 die oben angegebene Bedeutung hat, in an sich bekannter Weise mit einem reaktionsfähigen Ester des Methylalkohols umsetzt o) oder ein 1,2,4-Benzothiadiazin-1,1-dioxydderivat der allgemeinen Formel IV in der R2 und R5 die oben angegeben Bendeutung hat, mittels Alkalimetallborhydriden oder elektrolytisch reduziert und die erhaltene Verbindung der allgemeinen Formel I gewiinschtenfalls in an sich bek mnter Weise in ein Metallsalz überführt.The invention therefore relates to 3,4-dihydro-1,2,4-benzothiadiazine-l, l-dioxides of the general formula 1 in which R2 denotes a methyl or betyl eder benzyl group and R5 denotes a hydrogen atom or a methyl group. and salts of these compounds. According to patent (DAS 1 112 079), they are obtained if one has either a) a sulfamylaniline compound of the general formula II in which R5 has the abovementioned meaning, or its salts are reacted with an aldehyde of the general distance R2-CHO, in which R2 has the abovementioned denaturation, or b) a 3,4-dihydro-1,2,4-benzothiadiazine 1,1-dioxide derivative of the general formula III in which R2 has the meaning given above, reacts in a manner known per se with a reactive ester of methyl alcohol o) or a 1,2,4-benzothiadiazine-1,1-dioxide derivative of the general formula IV in which R2 and R5 have the meaning given above, reduced by means of alkali metal borohydrides or electrolytically and the compound of the general formula I obtained is, if desired, converted into a metal salt in a manner known per se.
Die Erfindung wird in den nachfolgenden Beispielen nocher beschrieben. Die Temperaturen sind in Celsiusgraden angegeben. The invention is further described in the following examples. The temperatures are given in degrees Celsius.
Beispiel 1 : 9,4 g 3-Methyl-6-chlor-7-sulfamyl-3,4-dihydro-1,2,4-benzothiediazin-1,1-dioxy6d werden in einer Mischung von 33 cm3 einer lnormalen nässrigen matriunhydroixydlösung und 120 cm3 Wasser gelöst. Von unlöslichen wird abfiltriert, dann auf 10° gekühlt, 24, g Dimethylaulfat zugegeben und bei dieser Temperatur 1 Stunde stehen gelassen. Man hält eine weitere Stunde bei Raumtempoerstur, filteriert die Renaktionsmischung und kristullisiert den Rückstand 2mla aus einer 1:1-Mischung aus Äthanol und wasser um. max erhält so 0,9 g 2,3-dimethyl-6-ohlor-7-aulfamyl-3,4-dihydro-1,2,4-bensothiadiazin-1,1-diöthyd von F. 274-276°. die Umkristallisctionsmultterluaugne werden eingetngt. wheel der Rückstand fest wird und sich, aus Methanol Kristallisieren lässt. Man kristalisiert aus wässrigen Äthanbol um. Example 1: 9.4 g of 3-methyl-6-chloro-7-sulfamyl-3,4-dihydro-1,2,4-benzothiediazine-1,1-dioxy6d are in a mixture of 33 cm3 of a normal aqueous matriunhydroxyd solution and 120 cm3 of water. Insoluble is filtered off, then cooled to 10 °, 24 g of dimethyl sulfate were added and the mixture was left to stand at this temperature for 1 hour. You hold at room pace for another hour, filter the reaction mixture and crystallized the residue 2mla from a 1: 1 mixture of ethanol and water around. max thus receives 0.9 g of 2,3-dimethyl-6-chloro-7-aulfamyl-3,4-dihydro-1,2,4-bensothiadiazine-1,1-diothyd from F. 274-276 °. the recrystallization results are collected. wheel the The residue solidifies and can be crystallized from methanol. You crystallize from aqueous ethanbol.
Dus 2,3-Dimethyl-6-chlor-7-(N-methyl-aulfmyl)-3,4-dihydro-1,2,4-bezethoiedazin-1,1-dienyd achmilzt brei 248-231°, Ausbeute 0,2 g.Dus 2,3-dimethyl-6-chloro-7- (N-methyl-aulfmyl) -3,4-dihydro-1,2,4-bezethoiedazin-1,1-diene achmilzt porridge 248-231 °, yield 0.2 g.
Das Ausgengsmaterial läst sich wie folgt erhlaten: Eine Mischung von 2,9 g 5-Chlor-2,4-disulfamylanilin, 20 cm3 wasserfreiem Diäthylenglykol-dimethyläther, 0,44 g Acetaldehyd undf 0,5 cm3 einer Schlatäurelösung in Essigsäureäthylester (109,5 g Chrlowasserstoffsäure pro Loite) wird auf 80-90° erhitzt und 1 stunde bei dieser Temeratur schalter. die R@@ktionsmischeung wird unter verminderten Druck eingeengt, dann Wasser zugefügt und das auskristallisierte Produkt abfilteriert. Das so erhaltene 3-Methyl-6-chlor-7-sulfamyl-3,4-dihydro-1,2,4-benzothiadiazin-1,1-dioxyd vom F. 29-260° Igest sich aus wässrigem Äthanol umkristallisieren Beispiel3! err.a.w,ranrs Behandelt man eine Lösung des 3-Benzyl-6-chlor-7-sulfamyl-3. 4-dihydro-1,2,4-benzothiadiazin-1,1-dioxyds in wässrigem Natriumhydroxyd mit Dimethylsulfat bei 10-205 1 Stunde und eine weltere Stunde bei Raumtemperatur, so erhält man eine Mischung des 2-Methyl-3-benzyl-6-chlor-7-sulfamyl-3,4-dihydro-1,2,4-benzothiadiazin-1,1-dixoyds und das 2-Mehyl-3-benzyl-6-chlor-7-N-methylsulfamyl-3,4-dihydro-1,2,4-benzo-.''.....','.-thiadiazin-1,1-dioxyds, welche sich durch fraktionieryte Kristallisation in hire Komponenten zerlegen lässt. The starting material can be obtained as follows: A mixture of 2.9 g of 5-chloro-2,4-disulfamylaniline, 20 cm3 of anhydrous diethylene glycol dimethyl ether, 0.44 g of acetaldehyde and 0.5 cm3 of a Schlatic acid solution in ethyl acetate (109.5 g hydrofluoric acid per Loite) is heated to 80-90 ° and 1 hour at this Temperature switch. the r @@ ctionsmixture is under diminished pressure concentrated, then water was added and the product which had crystallized out was filtered off. The 3-methyl-6-chloro-7-sulfamyl-3,4-dihydro-1,2,4-benzothiadiazine-1,1-dioxide thus obtained with a temperature of 29-260 ° Igest recrystallize from aqueous ethanol Example3! err.a.w, ranrs If a solution of 3-benzyl-6-chloro-7-sulfamyl-3 is treated. 4-dihydro-1,2,4-benzothiadiazine-1,1-dioxyds in aqueous sodium hydroxide with dimethyl sulfate at 10-205 for 1 hour and one world Hour at room temperature, a mixture of 2-methyl-3-benzyl-6-chloro-7-sulfamyl-3,4-dihydro-1,2,4-benzothiadiazine-1,1-dixoyds is obtained and the 2-methyl-3-benzyl-6-chloro-7-N-methylsulfamyl-3,4-dihydro-1,2,4-benzo -.''..... ',' .- thiadiazin-1 , 1-dioxyds, which can be broken down into components through fractional crystallization.
Das als Ausgangsastoff verwendete 3-Benzyl-6-chlor-7-sulfmyl-3,4-dihydro-1,24-benzothiadiazin-1,1-dioxyd lässyt sich wie folgt erhalten : ; Zu einer Ldsung von 2,9 g 5-Chlor-2,4-disulfmaylaniln in 15 c2 Diathylenglykol-diMethylather gibt man 1, 2 g Phenylaeetaldehyd und 0, 5 cm3 einer gesättigten Salzsäurelosung in Essigsäureäthylester, Die Reatkionsmischung wird 2 Stunden auf 90-100° erhitzt, dann unter vermindertem Druck eingedampft. Der Rückstand wird mit Wacoer versetzt, worauf ein sirup8ser Niederschlag entsteht. Man dekantiert das tue Atam@l.B&sge'@pMle8Bsy°6s@7I@Eij4 HtttS' t eY cfS °tra,.,. ^rJaL''cim. ua : '""~~gc ec 'cl. The 3-benzyl-6-chloro-7-sulfmyl-3,4-dihydro-1,24-benzothiadiazine-1,1-dioxide used as the starting material can be obtained as follows:; To a solution of 2.9 g of 5-chloro-2,4-disulfmaylaniln 1, 2 g of phenylaeetaldehyde and 0, 5 cm3 of a saturated hydrochloric acid solution in ethyl acetate, the reaction mixture is heated to 90-100 ° for 2 hours, then evaporated under reduced pressure. Of the Wacoer is added to the residue, whereupon a syrupy precipitate forms. You decant that do Atam @ l.B & sge '@ pMle8Bsy ° 6s @ 7I @ Eij4 HtttS 't eY cfS ° tra,.,. ^ rJaL''cim. including: '"" ~~ gc ec' cl.
&8d. 'ssmLC. Csrri='"'te m, b- °. S .'"881 b°, Rut EineMatm.g@10~3-a-BMtyl-6-ele-Tslaa Beispiel @: Eine Lösung von 10,6 g 3-n-Butyl-6-chlor-7-sulfamyl-3,4-dijhydro-1,2,4-benzethiadiezin-1,1-dioxyd in 66 cm3 einer Ino, wässrigen Natriumhydroxydlösung und 120 cm3 wasser Midauf§0bkahlt?ms?-i.E@"S.Mlf&tIsagsamsgegeben. Dass rührt man die Rascktisemichung 1 Stunde bei d3 Tls&6'° dazm a ; y ;. r 0ib'' 'F'r°' tM@3trahl@t3B&1niE@S&sy@yl@step.DiorgaEi sco§ehi<8htwirdb@rNaEssa.gokseesLsung MittelaiBgesNpft, ?0':eE.oMisehmgvon ung von 2-.Meyl-3a-ty3L--.eM ?''7s2.yl3a4iro'='l4-b@ss@thiMisiBlal''"öiM'-ragfsyln'-t3,-6@hlos'-T r4ct : b~, a, r=8m di d (ixQ$QcJA 4 f9V >'-.. i9 iide'3. ; 1 . ? &. Cs'. db Q's '981GOdl (SidE'Z-.& 8d. 'ssmLC. Csrri = '"' te m, b- °. S. '" 881 b °, Rut EineMatm.g@10~3-a-BMtyl-6-ele-Tslaa Example @: A solution of 10.6 g of 3-n-butyl-6-chloro-7-sulfamyl-3,4-dihydro-1,2,4-benzethiadiezine-1,1-dioxide given in 66 cm3 of an ino, aqueous sodium hydroxide solution and 120 cm3 of water Midauf§0bkahlt? ms? -i.E @ "S.Mlf & tIsagsams. That you stir the Rascktisemichung for 1 hour at d3 Tls & 6 '° dazm a; y;. r 0ib '' 'F'r °' tM @ 3trahl @ t3B & 1niE @ S & sy @ yl @ step.DiorgaEi sco§ehi <8htwirdb@rNaEssa.gokseesLsung MittelaiBgesNpft,? 0 ': eE.oMisehmgvon ung of 2-.Meyl-3a-ty3L -. eM? '' 7s2.yl3a4iro '=' l4-b @ ss @ thiMisiBlal '' "öiM'-ragfsyln'-t3, -6 @ hlos'-T r4ct: b ~, a, r = 8m di d (ixQ $ QcJA 4 f9V> '- .. i9 iide'3.; 1.? &. Cs'. db Q's' 981GOdl (SidE'Z-.
Schäumen); Ausbeute 3,9 gFoam); Yield 3.9g
Claims (3)
Applications Claiming Priority (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US71845258A | 1958-03-03 | 1958-03-03 | |
| US72724258A | 1958-04-09 | 1958-04-09 | |
| US74058258A | 1958-06-09 | 1958-06-09 | |
| US75162058A | 1958-07-29 | 1958-07-29 | |
| US76448258A | 1958-09-29 | 1958-09-29 | |
| DEC0024176 | 1959-02-27 | ||
| DEC0024177 | 1959-02-27 | ||
| DEC0024176 | 1959-02-27 | ||
| DEC0028409 | 1959-02-27 | ||
| DEC0024178 | 1959-02-27 | ||
| DEC0028408 | 1959-02-27 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1445006A1 true DE1445006A1 (en) | 1968-10-24 |
| DE1445006B2 DE1445006B2 (en) | 1975-05-07 |
| DE1445006C3 DE1445006C3 (en) | 1976-01-22 |
Family
ID=
Also Published As
| Publication number | Publication date |
|---|---|
| OA03826A (en) | 1971-12-24 |
| DE1445005A1 (en) | 1968-10-24 |
| FR1217929A (en) | 1960-05-06 |
| CH377365A (en) | 1964-05-15 |
| FR1264468A (en) | 1961-06-23 |
| CH371454A (en) | 1963-08-31 |
| DE1112079B (en) | 1961-08-03 |
| DE1445574A1 (en) | 1969-01-16 |
| CH376514A (en) | 1964-04-15 |
| DE1445008A1 (en) | 1968-10-24 |
| OA01178A (en) | 1969-01-25 |
| GB861367A (en) | 1961-02-22 |
| DE1445007A1 (en) | 1968-10-24 |
| MY6200051A (en) | 1962-12-31 |
| DE1445006B2 (en) | 1975-05-07 |
| CH387642A (en) | 1965-02-15 |
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