DE1770731A1 - New blood sugar lowering sulfonamides - Google Patents
New blood sugar lowering sulfonamidesInfo
- Publication number
- DE1770731A1 DE1770731A1 DE19681770731 DE1770731A DE1770731A1 DE 1770731 A1 DE1770731 A1 DE 1770731A1 DE 19681770731 DE19681770731 DE 19681770731 DE 1770731 A DE1770731 A DE 1770731A DE 1770731 A1 DE1770731 A1 DE 1770731A1
- Authority
- DE
- Germany
- Prior art keywords
- general formula
- carbonamido
- meaning given
- given above
- compound
- Prior art date
- Legal status (The legal status 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 status listed.)
- Pending
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/69—Benzenesulfonamido-pyrimidines
Landscapes
- 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
.:...- .. ; \r 17707^1.: ...- ..; \ r 17707 ^ 1
Neue blutauckeijsenkende SulfonamideNew antihypertensive sulfonamides
Gegenstand der Erfindung sind neue Sulfonamide der allgemeinenThe invention relates to new sulfonamides of general
Formelformula
\-S02-SH-\ -S0 2 -SH-
worin R, und R2 gleich oder verschieden sind und Wasserstoffetome oder Alkyl-, Alkoxy- oder Alkylmercaptoreste mit 1-4 Kohlenstoffatomen, R, ein Alkyl- oder Alkoxyrest, der auch % ringgeschlossen sein und weitere Sauerstoffatome enthalten kann und.l - 8 Kohlenstoffatome enthalten soll, R^ ein Wasserstoffatom oder einen Alkylrest mit 1-4· Kohlenstoffatomen, X ein Sauerstoffoder Schwefelatom oder eine NH-Gruppe, T einen Alkylenrest mit 1-4 Kohlenstoffatomen und η eine Zahl von 0 bis 4 bedeuten, sowie deren Salze mit physiologisch verträglichen Basen.wherein R, and R2 are the same or different and Wasserstoffetome or alkyl, alkoxy or alkylmercapto of 1-4 carbon atoms, R, is an alkyl or alkoxy group, which also can contain% be ring closed, and additional oxygen atoms und.l - contain from 8 carbon atoms R ^ should be a hydrogen atom or an alkyl radical with 1-4 carbon atoms, X an oxygen or sulfur atom or an NH group, T an alkylene radical with 1-4 carbon atoms and η a number from 0 to 4, as well as their salts with physiologically compatible Bases.
Die neuen Verbindungen besitzen eine sehr gute Wirkung als Antidiabetica. So zeigen die neuen Verbindungen bei der Ratte in Dosen von 0,1 - 1,0 mg/kg Körpergewicht unter den Standardmeßmethoden ( eine Senkung des Blutzuckerspiegels um bis zu über 35 % des Ausgangswertes· The new compounds have a very good effect as antidiabetics. The new compounds show in the rat in doses of 0.1 - 1.0 mg / kg body weight under the standard measuring methods (a reduction in blood sugar level by up to more than 35% of the initial value
Zum therapeutischen Gebrauch können die neuen Substanzen verabfolgt werden als freie Sulfonamide oder als Salze mit physiologisch verträglichen Basen. Als Basen kommen beispielsweise in Fraget Natrium-, Lithium, Calcium-, Ammoniumhydroxid; Amine, wie Methyl- . glukamin, Morpholin, Äthanolamin. Auch Mischungen der freien Sulfonamide mit einem geeigneten Alkolikarbonat bzw. - hydrogencarbonatThe new substances can be administered for therapeutic use are available as free sulfonamides or as salts with physiologically compatible bases. As bases, for example, come in question Sodium, lithium, calcium, ammonium hydroxide; Amines, such as methyl-. glucamine, morpholine, ethanolamine. Also mixtures of the free sulfonamides with a suitable alkali carbonate or bicarbonate
109848/1916 _p_109848/1916 _p_
kommen in Betracht. Von besonderem Interesse sind Salze der Sulfonamide mit Basen, die selbst auck eine blutsuckersenkende Wirkung besitzen, vie z.B. Butylbiguanid.is being brought up for consideration. Of particular interest are salts of sulfonamides with bases, which themselves also have a blood-sugar-lowering effect such as butyl biguanide.
Die Konfektionierung der Substanzen kann ohne oder mit den in der gelenisehen Pharmazie üblichen Zusätzen, Tragersubstanzen, Geschmackskorrigenzien usw. erfolgen, und zwar beispielsweise in Pulverform, als Tabletten, Dragees, Kapseln, Pillen, in Form von Suspensionen oder Lösungen.The packaging of the substances can be carried out with or without the in the common pharmaceutical additives, carrier substances, flavor corrections etc. take place, for example in powder form, as tablets, coated tablets, capsules, pills, in the form of suspensions or solutions.
Die Herstellung der neuen Sulfonamide kann erfolgen dadurch,'daß man a) eine Verbindung der allgemeinen FormelThe preparation of the new sulfonamides can be done by 'that one a) a compound of the general formula
worin R, , &>, R^, n, X und T die oben angegebene Bedeutung haben, mit einem substituierten Malondialdehyd der allgemeinen Formelwhere R,, &>, R ^, n, X and T have the meaning given above, with a substituted malondialdehyde of the general formula
H
t H
t
worin IU dasselbe wie oben bedeutet und in dem die Aldehydgruppen auch funktionell abgewandelt sein können, ringschließend kondensiert oder b) eine Verbindung der allgemeinen Formelwhere IU means the same as above and where the aldehyde groups can also be functionally modified, condensed or closed ring b) a compound of the general formula
.-3-109841/1916.-3-109841 / 1916
In der Rw R2' 1V n' ** "1^ Y die.°^en angegebene Bedeutung besitzen und Q ein Halogenatom, vorzugsweise Chlor, bedeutet, rait einem 2-Amino-5-R,-pyrimidin, worin R, die oben genannte ! Bedeutung besitzt, umsetzt öderIn Rw R 2 '1 V n' ** "1 ^ Y. ° ^ s have the meaning given and Q is a halogen atom, preferably chlorine, Rait a 2-amino-5-R, pyrimidine, wherein R, has the meaning mentioned above, converts or
♦ <♦ <
c) eine Verbindung der allgemeinen Formel . .c) a compound of the general formula. .
U» worin R^, R2* R4» n, X und Y die oben angegebene Bedeutung . / besitzen, in freier Form oder als Alkalisalz mit einer ' · " Verbindung der allgemeinen FormelU »in which R ^, R 2 * R4» n, X and Y have the meanings given above. / own, in free form or as an alkali salt with a '· "compound of the general formula
worin R-z die oben genannte Bedeutung besitzt und L ein Halogen- ' ■ ■ atom, vorzugsweise Chlor, ■ eine Trialkylammoniumgruppe oder eine niedereAlkylsulfonylgruppe bedeutet, umsetzt oderwherein R-z has the abovementioned meaning and L is a halogen- '■ ■ atom, preferably chlorine, ■ a trialkylammonium group or a means lower alkylsulfonyl group, reacts or
d) eine Verbindung der allgemeinen Formeld) a compound of the general formula
worin R,, R2* n, und X dasselbe wie oben bedeuten, oder ein / ,wherein R ,, R 2 * n, and X are the same as above, or a /,
- ■- ■
mm äquivalent reaktionsfähiges Derivat der entsprechenden Säureequivalent reactive derivative of the corresponding acid
* alt'einem Arain der allgemeinen Formel* alt'an area of the general formula
worin R^ und R^ die oben genannte Bedeutung haben, reagieren laßt und die so erhaltenen Verbindungen gegebenenfalls in die Salze mit physiologisch vertraglichen Basen überfuhrt«wherein R ^ and R ^ have the meaning given above, let react and the compounds obtained in this way are optionally converted into the salts with physiologically compatible bases "
SCHERING AG , - 4 -SCHERING AG, - 4 -
177Ö731177Ö731
Die für die Reaktion gemäß a) verwendeten Malonaldehydderivate · laccon ο loh z.B. daduroh sowihnen, dal; r ro:~ Aldehydaoetale der all· gemeinen Formel . .The malonaldehyde derivatives used for the reaction according to a) laccon ο loh e.g. daduroh as well as dal; r ro: ~ aldehyde aoetal of all common formula. .
in der R1 einen niederen bis mittleren Alkylrest bedeutet, nach bekannten Methoden formyliert. · ·in which R 1 is a lower to middle alkyl radical, formylated by known methods. · ·
BAD ORIGINAL 109848/1916 BAD ORIGINAL 109848/1916
-1I-.- 1 I-.
Beispiel jExample j *~* ~
33 g 2-(4-ß-Aminoäthylbenzolsul!tonamido)-5-i8o'butylpyriiiidin (hergestellt durch Umsetzung von Carbäthoxyaminoäthylbenzol~ eulfochlorid mit 2-Amino-5-isobutylpyrimidin und anschließende Verseifung der Carbäthoxyaminoäthylgruppe zur Aminoäthylgruppe, Schmelzpunkt 223 0C), werden in 100 ml Pyridin gelöst und nach Zugabe von 16 g 5-MethyliBoxazol-3-carbonsäurechlorid 2 Stunden auf 60 0C erhitzt. DanaSh wird das Pyridin abdestilliert und der Rückstand mit Wasser versetzt. Nach Ansäuern mit Salzsäure wird die Fällung abgesaugt und aus Methylglykol umkristallisiert. Man erhält so 3° g 2[h— (5-Methylisoxazolyl-3-carbonamido)-äthylbenzolsulfonamido7-5-isobutylpyrimidin mit dem Schmelzpunkt 223 0C.33 g 2- (4-ß-Aminoäthylbenzolsul! Tonamido) -5-i8o'butylpyriiiidin (prepared by reacting Carbäthoxyaminoäthylbenzol ~ eulfochlorid with 2-amino-5-isobutylpyrimidin and subsequent saponification of the Carbäthoxyaminoäthylgruppe to Aminoäthylgruppe, melting point 223 0 C), dissolved in 100 ml of pyridine and, after addition of 16 g of 5-MethyliBoxazol-3-carbonyl chloride for 2 hours at 60 0 C. DanaSh, the pyridine is distilled off and the residue is mixed with water. After acidification with hydrochloric acid, the precipitate is filtered off with suction and recrystallized from methylglycol. Is obtained as 3 g of 2 ° [h- (5-methylisoxazolyl-3-carboxamido) -äthylbenzolsulfonamido7-5-isobutylpyrimidin with the melting point 223 0 C.
In analoger Weise erhält man bei Verwendung entsprechender Ausgang sprodukteIn an analogous way one obtains when using the corresponding output products
2/4-(5-Methylieoxazol~3-carbonamido)-äthylbenzolsulfonamido7-2 / 4- (5-Methylieoxazol ~ 3-carbonamido) -äthylbenzenesulfonamido7-
5-n-butoxypyrimidin, Schmelzpunkt 195 0C,5-n-butoxypyrimidine, melting point 195 0 C,
2 ß— (5-Methylisoxazol-3-carbonamido)-äthylbenzolsulfonamido/-2 ß- (5-methylisoxazole-3-carbonamido) ethylbenzenesulfonamido / -
5-isopropoxypyrimidin, Schmelzpunkt 221 0C1 t5-isopropoxypyrimidine, melting point 221 0 C 1 t
2£4-(5-Methylisoxazol-3-carbonamido)-äthylbenzolsulfonamido_/-5-methoxyäthoxypyrimidin, Schmelzpunkt 205 0C, 2£4~(5-Methylisoxazol-3-carbonamido)-methylbenzolsulfonamido7-2 £ 4- (5-methylisoxazole-3-carboxamido) -äthylbenzolsulfonamido _ / - 5-methoxyäthoxypyrimidin, mp 205 0 C, 2 £ 4 ~ (5-methylisoxazole-3-carboxamido) -methylbenzolsulfonamido7-
5-isobutylpyrimidin, Schmelzpunkt 253 0C1 5-isobutylpyrimidine, melting point 253 0 C 1
2-{4-(3»5-bis-methylmerkaptoisothiazolyl-4~carbonamido)-äthylbenzol-eulfonamidoj-5-ii-propo3cypyrimidin 2- {4- (3 »5-bis-methylmercaptoisothiazolyl-4-carbonamido) -ethylbenzene-sulfonamidoj-5-ii-propo3cypyrimidine
Schmelzpunkt 182 0C.Melting point 182 0 C.
109848/1916109848/1916
CC. ί ■ , ,;ί ■,,;
Beispiel 2 .·.-... Example 2. ·.-...
35 g 4-(3-Methylpyrazol-5-carbon^lamino)-äthgrlbenzolsulfoguanidin (Schmolzpunkt 2680C) werden mit einer Lösung von 16 g cc-Isobutylß-dimethylaminoacrolein (dargestellt nach der Methode von VlIsmeier aus Isobutylacetaldehyddiäthylacetal, Siedepunkt (0,OJJ Torr) 106°C)und 3 g Natrium in 250 ml Methanol 5 Stunden zum Sieden erhitzt. Das Methanol wird dann abdestilliert und der Rückstand in Wasser gelöst. Nach Klären der Lösung mit Kohle erhält man durch Ansäuern mit Salzsäure eine Fällung, die, umkristallistert aus Methylglykol, 29 g 2-^-(2-Methylpyrazol~5-carbonylamino)- _·· äthylbenzolsulfcnamido7-5-isobutyl'pyrlmidln mit dem Schmelzpunkt C ergibt. ■ ... . . .35 g of 4- (3-methylpyrazole-5-carbon ^ lamino) -äthgrlbenzenesulfoguanidin (melting point 268 0 C) are with a solution of 16 g of cc-isobutylß-dimethylaminoacrolein (prepared according to the method of VlIsmeier from isobutyl acetaldehyde diethyl acetal, boiling point (0, OJJ Torr) 106 ° C) and 3 g of sodium in 250 ml of methanol heated to boiling for 5 hours. The methanol is then distilled off and the residue is dissolved in water. After the solution has been clarified with charcoal, acidification with hydrochloric acid gives a precipitate which, recrystallized from methylglycol, 29 g of 2 - ^ - (2-methylpyrazole ~ 5-carbonylamino) - _ ·· ethylbenzenesulfcnamido7-5-isobutyl'pyrlmidln with the melting point C yields. ■ .... . .
35 g ^-(5-Methylisoxazol-3-carbonamido,)-äthylbenzolsulfona?nid-Natrium (Schmelzpunkt 2l6°C) werden in 250 ml Acetamid gelöst und mit 16,5 g 2-Chlor-5-isopropoxypyrimidin 6 Stunden bei 1500C gerührt. Danach wird das Acetamid abdestilliert und der Rückstand mit Wasser vernetzt. Man erhält eine Fällung, die nach Umkristallisieren aus Methylglykol 28 g 2-/^-(5-Methylisoxazol-3-carbonamido)-äthylbenzolsulfonajnido7-5-isopropoxypyrimidin "mit dem Schmelzpunkt 2180C ergibt.35 g ^ - (5-methyl-3-carbonamido,) - äthylbenzolsulfona nid sodium (melting point 2l6 ° C) are dissolved in 250 ml of acetamide and 16.5 g of 2-chloro-5-isopropoxypyrimidin 6 hours at 150 0? C stirred. The acetamide is then distilled off and the residue is crosslinked with water. This gives a precipitate, which after recrystallization from methylene glycol 28 g of 2 - / ^ - (5-methylisoxazole-3-carboxamido) -äthylbenzolsulfonajnido7-5-isopropoxypyrimidin "with a melting point gives 218 0 C.
108141/1916 -7108141/1916 -7
Claims (1)
a) eine Verbindung der allgemeinen Formel9.) Process for the preparation of compounds according to claim 1, characterized in that one
a) a compound of the general formula
b) eine Verbindung der allgemeinen Formelwhere R is the same as above and in which the aldehyde groups can also be functionally modified, ring-closed or condensed
b) a compound of the general formula
c) eine Verbindung der allgemeinen Formelin which R, Ro »Rj ,, n, X and Y have the meaning given above and Q is a halogen atom, preferably chlorine, with a 2-amino-5-R, pyrimidine, in which R ^ has the meaning given above owns, implements or
c) a compound of the general formula
Priority Applications (18)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19681770731 DE1770731A1 (en) | 1968-06-27 | 1968-06-27 | New blood sugar lowering sulfonamides |
BR208777/69A BR6908777D0 (en) | 1968-06-27 | 1969-05-14 | PROCESS FOR THE PREPARATION OF NEW SULPHONAMIDES |
DK300869AA DK123602B (en) | 1968-06-27 | 1969-06-03 | Analogous process for the preparation of sulfonamides. |
CH1669271A CH518971A (en) | 1968-06-27 | 1969-06-05 | Process for the production of new sulfonamides |
CH1669171A CH518970A (en) | 1968-06-27 | 1969-06-05 | Hypoglycaemic sulphonamidopyrimidines |
CH860269A CH518968A (en) | 1968-06-27 | 1969-06-05 | Process for the production of new sulfonamides |
ES368100A ES368100A1 (en) | 1968-06-27 | 1969-06-06 | New sulphonamides having a blood sugar lowering action |
IL32396A IL32396A (en) | 1968-06-27 | 1969-06-13 | Hypoglycemic benzene sulphonamido-2-pyrimidine derivatives |
GB30406/69A GB1268835A (en) | 1968-06-27 | 1969-06-16 | New sulphonamides having a blood sugar lowering action |
AT573169A AT289109B (en) | 1968-06-27 | 1969-06-17 | Process for the preparation of new heterocyclic compounds and their salts |
AT788770A AT291255B (en) | 1968-06-27 | 1969-06-17 | Process for the preparation of new heterocyclic compounds and their salts |
AT788870A AT291256B (en) | 1968-06-27 | 1969-06-17 | Process for the preparation of new heterocyclic compounds and their salts |
SE08952/69A SE357365B (en) | 1968-06-27 | 1969-06-24 | |
IE873/69A IE33175B1 (en) | 1968-06-27 | 1969-06-25 | New sulphonamides having a blood sugar lowering action |
FR696921467A FR2014300B1 (en) | 1968-06-27 | 1969-06-26 | |
NO2659/69A NO124374B (en) | 1968-06-27 | 1969-06-26 | |
NL6909960A NL6909960A (en) | 1968-06-27 | 1969-06-27 | |
BE735287D BE735287A (en) | 1968-06-27 | 1969-06-27 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19681770731 DE1770731A1 (en) | 1968-06-27 | 1968-06-27 | New blood sugar lowering sulfonamides |
Publications (1)
Publication Number | Publication Date |
---|---|
DE1770731A1 true DE1770731A1 (en) | 1971-11-25 |
Family
ID=5700618
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE19681770731 Pending DE1770731A1 (en) | 1968-06-27 | 1968-06-27 | New blood sugar lowering sulfonamides |
Country Status (14)
Country | Link |
---|---|
AT (3) | AT291255B (en) |
BE (1) | BE735287A (en) |
BR (1) | BR6908777D0 (en) |
CH (1) | CH518968A (en) |
DE (1) | DE1770731A1 (en) |
DK (1) | DK123602B (en) |
ES (1) | ES368100A1 (en) |
FR (1) | FR2014300B1 (en) |
GB (1) | GB1268835A (en) |
IE (1) | IE33175B1 (en) |
IL (1) | IL32396A (en) |
NL (1) | NL6909960A (en) |
NO (1) | NO124374B (en) |
SE (1) | SE357365B (en) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2048906A1 (en) * | 1970-10-06 | 1972-04-13 | Boehringer Mannheim Gmbh, 6800 Mannheim | Blood sugar lowering sulfonylaminopyrimidines and processes for their preparation |
CA2489355A1 (en) * | 2002-06-13 | 2003-12-24 | Qlt Inc. | Methods of using isothiazole derivatives to treat cancer or inflammation |
-
1968
- 1968-06-27 DE DE19681770731 patent/DE1770731A1/en active Pending
-
1969
- 1969-05-14 BR BR208777/69A patent/BR6908777D0/en unknown
- 1969-06-03 DK DK300869AA patent/DK123602B/en unknown
- 1969-06-05 CH CH860269A patent/CH518968A/en not_active IP Right Cessation
- 1969-06-06 ES ES368100A patent/ES368100A1/en not_active Expired
- 1969-06-13 IL IL32396A patent/IL32396A/en unknown
- 1969-06-16 GB GB30406/69A patent/GB1268835A/en not_active Expired
- 1969-06-17 AT AT788770A patent/AT291255B/en not_active IP Right Cessation
- 1969-06-17 AT AT573169A patent/AT289109B/en not_active IP Right Cessation
- 1969-06-17 AT AT788870A patent/AT291256B/en not_active IP Right Cessation
- 1969-06-24 SE SE08952/69A patent/SE357365B/xx unknown
- 1969-06-25 IE IE873/69A patent/IE33175B1/en unknown
- 1969-06-26 FR FR696921467A patent/FR2014300B1/fr not_active Expired
- 1969-06-26 NO NO2659/69A patent/NO124374B/no unknown
- 1969-06-27 NL NL6909960A patent/NL6909960A/xx unknown
- 1969-06-27 BE BE735287D patent/BE735287A/xx not_active Expired
Also Published As
Publication number | Publication date |
---|---|
FR2014300B1 (en) | 1973-01-12 |
AT291255B (en) | 1971-07-12 |
FR2014300A1 (en) | 1970-04-17 |
IL32396A (en) | 1972-06-28 |
BR6908777D0 (en) | 1973-01-23 |
DK123602B (en) | 1972-07-10 |
IL32396A0 (en) | 1969-08-27 |
ES368100A1 (en) | 1971-05-01 |
BE735287A (en) | 1969-12-29 |
CH518968A (en) | 1972-02-15 |
NL6909960A (en) | 1969-12-30 |
GB1268835A (en) | 1972-03-29 |
NO124374B (en) | 1972-04-10 |
AT289109B (en) | 1971-04-13 |
IE33175L (en) | 1969-12-27 |
AT291256B (en) | 1971-07-12 |
IE33175B1 (en) | 1974-04-03 |
SE357365B (en) | 1973-06-25 |
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