CH596193A5 - Dihalobenzoguanamines with anti-ulcus activity - Google Patents
Dihalobenzoguanamines with anti-ulcus activityInfo
- Publication number
- CH596193A5 CH596193A5 CH1652175A CH1652175A CH596193A5 CH 596193 A5 CH596193 A5 CH 596193A5 CH 1652175 A CH1652175 A CH 1652175A CH 1652175 A CH1652175 A CH 1652175A CH 596193 A5 CH596193 A5 CH 596193A5
- Authority
- CH
- Switzerland
- Prior art keywords
- triazine
- ammonia
- dihalobenzoguanamines
- ulcus
- activity
- Prior art date
Links
- 230000000694 effects Effects 0.000 title abstract description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 23
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 9
- IHDBZCJYSHDCKF-UHFFFAOYSA-N 4,6-dichlorotriazine Chemical class ClC1=CC(Cl)=NN=N1 IHDBZCJYSHDCKF-UHFFFAOYSA-N 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 description 9
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
- 239000013078 crystal Substances 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000000921 elemental analysis Methods 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 5
- 235000011114 ammonium hydroxide Nutrition 0.000 description 5
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 208000025865 Ulcer Diseases 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 231100000397 ulcer Toxicity 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- VCJQGRGZZDMYIR-UHFFFAOYSA-N 2,4-dichloro-6-(2,4-dichlorophenyl)-1,3,5-triazine Chemical compound ClC1=CC(Cl)=CC=C1C1=NC(Cl)=NC(Cl)=N1 VCJQGRGZZDMYIR-UHFFFAOYSA-N 0.000 description 1
- IVOPPANFWGHWEH-UHFFFAOYSA-N 2,4-dichloro-6-(2,5-dibromophenyl)-1,3,5-triazine Chemical compound ClC1=NC(Cl)=NC(C=2C(=CC=C(Br)C=2)Br)=N1 IVOPPANFWGHWEH-UHFFFAOYSA-N 0.000 description 1
- YDMCWQDHUSEJBQ-UHFFFAOYSA-N 2,4-dichloro-6-(2,5-dichlorophenyl)-1,3,5-triazine Chemical compound ClC1=CC=C(Cl)C(C=2N=C(Cl)N=C(Cl)N=2)=C1 YDMCWQDHUSEJBQ-UHFFFAOYSA-N 0.000 description 1
- SSJULALZARBQAX-UHFFFAOYSA-N 2,4-dichloro-6-(3,4-dichlorophenyl)-1,3,5-triazine Chemical compound ClC1=NC(Cl)=NC(C=2C=C(Cl)C(Cl)=CC=2)=N1 SSJULALZARBQAX-UHFFFAOYSA-N 0.000 description 1
- BODHMBNUPDISMO-UHFFFAOYSA-N 2,4-dichloro-6-(3,5-dichlorophenyl)-1,3,5-triazine Chemical compound ClC1=CC(Cl)=CC(C=2N=C(Cl)N=C(Cl)N=2)=C1 BODHMBNUPDISMO-UHFFFAOYSA-N 0.000 description 1
- CXIXABFFQFDTIA-UHFFFAOYSA-N 2-(5-bromo-2-chlorophenyl)-4,6-dichloro-1,3,5-triazine Chemical compound ClC1=CC=C(Br)C=C1C1=NC(Cl)=NC(Cl)=N1 CXIXABFFQFDTIA-UHFFFAOYSA-N 0.000 description 1
- QHHJLAYFGXSOBP-UHFFFAOYSA-N 6-(2,4-dichlorophenyl)-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C(=CC(Cl)=CC=2)Cl)=N1 QHHJLAYFGXSOBP-UHFFFAOYSA-N 0.000 description 1
- GZKVTJOEGGXBBF-UHFFFAOYSA-N 6-(2,5-dibromophenyl)-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C(=CC=C(Br)C=2)Br)=N1 GZKVTJOEGGXBBF-UHFFFAOYSA-N 0.000 description 1
- ATCGGEJZONJOCL-UHFFFAOYSA-N 6-(2,5-dichlorophenyl)-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C(=CC=C(Cl)C=2)Cl)=N1 ATCGGEJZONJOCL-UHFFFAOYSA-N 0.000 description 1
- DPLWHHAFNKDYDU-UHFFFAOYSA-N 6-(3,4-dichlorophenyl)-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C=C(Cl)C(Cl)=CC=2)=N1 DPLWHHAFNKDYDU-UHFFFAOYSA-N 0.000 description 1
- NZHXBSDOZWURFJ-UHFFFAOYSA-N 6-(3,5-dichlorophenyl)-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C=C(Cl)C=C(Cl)C=2)=N1 NZHXBSDOZWURFJ-UHFFFAOYSA-N 0.000 description 1
- RNXNJHBTMRPHBZ-UHFFFAOYSA-N 6-(5-bromo-2-chlorophenyl)-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C(=CC=C(Br)C=2)Cl)=N1 RNXNJHBTMRPHBZ-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 230000000767 anti-ulcer Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000012320 chlorinating reagent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- QPJDMGCKMHUXFD-UHFFFAOYSA-N cyanogen chloride Chemical compound ClC#N QPJDMGCKMHUXFD-UHFFFAOYSA-N 0.000 description 1
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/16—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom
- C07D251/18—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom with nitrogen atoms directly attached to the two other ring carbon atoms, e.g. guanamines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (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)
Abstract
Dihalobenzoguanamines with anti-ulcus activity prepd. by reacting dichlorotriazines with ammonia
Description
Wir haben die Synthese von neuen Benzoguanaminen mit nützlichen pharmakologischen Eigenschaften untersucht.
Kürzlich wurde das neue Verfahren zur Herstellung von Dihalogenbenzoguanaminen entwickelt und die vorliegende Erfindung vervollständigt.
Erfindungsgemäss erhält man durch Umsetzen von Dichlortriazinen der allgemeinen Formel
EMI1.1
worin R eine Dihalogenphenylgruppe bedeutet, mit Ammoniak in einer Stufe Dihalogenbenzoguanamine der allgemeinen Formel
EMI1.2
worin R wie in Formel I definiert ist.
Eine Verbindung der allgemeinen Formel I, die als Edukt verwendet wird, kann durch Chlorierung der entsprechenden Dihydroxyverbindung mit einem Chlorierungsmittel wie Phosphorpentachlorid, Umsetzung von Benzonitril mit Cyanogenchlorid oder Umsetzung eines Phenyl-Grignard-Reagens mit Cyanurchlorid hergestellt werden.
Die Umsetzung einer Verbindung der Formel I mit Ammoniak kann bei Verwendung von konzentrierter wässriger Ammoniaklösung oder gasförmigem Ammoniak bei einer Temperatur von etwa 100" C in etwa 1 Stunde durchgeführt werden.
Die Umsetzung wird vorzugsweise in einem abgeschlossenen Rohr durchgeführt, um die Verdampfung von Ammoniak zu verhindern. Es kann irgendein Lösungsmittel verwendet werden, welches Edukt und Ammoniak lösen kann, vorteilhafterweise verwendet man in der Regel ein hydrophiles Lösungsmittel wie einen niederen Alkohol und Dioxan. Im allgemeinen resultiert eine extrem hohe Ausbeute.
Die gemäss vorliegender Erfindung erhältlichen Verbindungen sind in Tabelle I zusammengestellt ebenso wie ihre Wirksamkeit in der Hemmung von Shay's Geschwür bei Ratten, einem Kriterium der Nützlichkeit solcher Verbindungen. Ausser der Verbindung Nr. 2 sind alle neu. Das erfindungsgemässe Verfahren zur Herstellung dieser Verbindung unterscheidet sich vollständig von bisher bekannten Verfahren zu dessen Herstellung. Weiterhin haben wir als erste die Anti Geschwür-Wirksamkeit der Verbindung Nr. 2 entdeckt. Bisher wurde keine Literaturangabe über die biologische Wirksamkeit der Verbindung Nr. 2 gefunden.
Tabelle I Verbindung Dosierung Hemmung von (entspricht der Nummer) [mg/kg] (i.p.) Geschwüren [%] des Beispiels 1 20 100 2 20 91 3 20 80 4 20 100 5 20 43 6 20 86
Die vorliegende Erfindung wird durch die folgenden Beispiele ausführlicher beschrieben.
Beispiel 1
Eine Lösung von 5,0 g 2,4-Dichlor-6-(2,5-dichlorphenyl)s-triazin (Smp. 133-134 C) in 100 ml Dioxan wird mit 20 ml 28 %igem wässrigem Ammoniak gemischt und in einem geschlossenen Rohr während 1 Stunde auf 100" C erwärmt. Nach dem Abkühlen wird die Reaktionsmischung bei reduziertem Druck zur Trockne eingedampft und dem Rückstand Wasser zugegeben. Die ausgefallenen Kristalle werden abfiltriert, mit Wasser gewaschen und aus Äthanol umkristallisiert, wobei 4,2 g 2,4-Diamino-6-(2,5-dichlorphenyl)-s-triazin, Smp.
270-271" C, erhalten werden.
Elementaranalyse:
Berechnet: C 42,21 H 2,76 N 27,35
Gefunden: C 42,22 H 2,58 N 27,50
Beispiel 2
Eine Lösung von 4,3 g 2,4-Dichlor-6- (3 ,4-dichlorphenyl) s-triazin (Smp. 146-148 C) in 200 ml Methanol, gesättigt mit gasförmigem Ammoniak, wird in einem geschlossenen Rohr eine Stunde lang bei 100" C erhitzt. Die Reaktionsmischung wird wie in Beispiel 1 aufgearbeitet und die abgetrennten Kristalle aus Methanol umkristallisiert, wobei 3,8 g 2,4-Diamino6-(3,4-dichlorphenyl)-s-triazin, Smp. 230-232 C, erhalten werden.
Elementaranalyse:
Berechnet: C 42,21 H 2,76 N 27,35
Gefunden: C 42,06 H 2,80 N 27,41
Beispiel 3
Eine Lösung von 5,0 g 2,4-Dichlor-6-(3,5-dichlorphenyl)- s-triazin (Smp. 151-154" C) in 100 ml Dioxan wird mit 20 ml 28 %igem wässrigem Ammoniak gemischt und in einem geschlossenen Rohr während 1 Stunde auf 100" C erhitzt. Die Reaktionsmischung wird wie in Beispiel 1 aufgearbeitet und die abgetrennten Kristalle aus Dioxan umkristallisiert, wobei 4,4 g 2,4-Diamino-6-(3 ,5-dichlorphenyl)-s-triazin, Smp. über 3000 C, erhalten werden.
Elementaranalyse:
Berechnet: C 42,21 H 2,76 N 27,35
Gefunden: C 42,56 H 2,49 N 27,50
Beispiel 4
Eine Lösung von 3,9 g 2,4-Dichlor-6-(2,4-dichlorphenyl)s-triazin (Smp. 115-117 C) in 100 ml Äthanol wird mit 20 ml 28 %igem wässrigem Ammoniak gemischt und in einem geschlossenen Rohr während 1 Std. bei 100" C erwärmt. Die Reaktionsmischung wird wie in Beispiel 1 aufgearbeitet und die abgetrennten Kristalle aus Aceton umkristallisiert, wobei 3,3 g 2,4-Diamino-6-(2,4-dichlorphenyl)-s-triazin, Smp. 205 bis 207 C, erhalten werden.
Elementaranalyse:
Berechnet: C 42,21 H 2,76 N 27,35
Gefunden: C 42,41 H 2,70 N 27,02
Beispiel 5
Eine Lösung von 2,1 g 2,4-Dichlor-6-(2,5-dibromphenyl)s-triazin (Smp. der rohen Kristalle 160-168 C) in 50 ml Dioxan wird mit 10 ml 28 %igem Ammoniak gemischt und während 1 Stunde bei 100" C erwärmt. Die Reaktionsmischung wird wie in Beispiel 1 aufgearbeitet und die abgetrennten Kristalle aus Dioxan umkristallisiert, wobei 1,2 g 2,4-Diamino-6 (2,5-dibromphenyl)-s-triazin, Smp. 272-274 C erhalten werden.
Elementaranalyse:
Berechnet: C 31,33 H 2,05 N 20,30
Gefunden: C 31,53 H 1,92 N 20,45
Beispiel 6
Eine Lösung von 1,0 g 2,4-Dichlor-6-(2-chlor-5-bromphenyl)-s-triazin (Smp. der rohen Kristalle 140-145 C) in 30 ml Dioxan wird mit 5 ml 28 %igem wässrigem Ammoniak gemischt und während einer Stunde bei 100" C erhitzt. Die Reaktionsmischung wird wie in Beispiel 1 aufgearbeitet und die abgetrennten Kristalle aus einer Mischung von Dioxan und Äthanol umkristallisiert, wobei 0,52 g 2,4-Diamino-6 (2-chlor-5-bromphenyl)-s-triazin, Smp. 280-282"C, erhalten werden.
Elementaranalyse:
Berechnet: C 35,97 H 2,35 N 23,30
Gefunden: C 36,01 H 2,34 N 23,19
We have studied the synthesis of new benzoguanamines with useful pharmacological properties.
Recently, the new process for producing dihalobenzoguanamines has been developed and the present invention has been completed.
According to the invention, reaction of dichlorotriazines of the general formula gives
EMI1.1
wherein R denotes a dihalophenyl group, with ammonia in one stage dihalobenzoguanamine of the general formula
EMI1.2
wherein R is as defined in formula I.
A compound of the general formula I which is used as starting material can be prepared by chlorinating the corresponding dihydroxy compound with a chlorinating agent such as phosphorus pentachloride, reacting benzonitrile with cyanogen chloride or reacting a phenyl-Grignard reagent with cyanuric chloride.
The reaction of a compound of the formula I with ammonia can be carried out in about 1 hour at a temperature of about 100 ° C. when using concentrated aqueous ammonia solution or gaseous ammonia.
The reaction is preferably carried out in a closed tube in order to prevent the evaporation of ammonia. Any solvent which can dissolve the starting material and ammonia can be used; a hydrophilic solvent such as a lower alcohol and dioxane is usually advantageously used. In general, the yield is extremely high.
The compounds obtainable according to the present invention are compiled in Table I, as are their effectiveness in inhibiting Shay's ulcer in rats, a criterion for the usefulness of such compounds. Except for connection no. 2, all are new. The process according to the invention for the preparation of this compound differs completely from previously known processes for its preparation. Furthermore, we were the first to discover the anti-ulcer activity of Compound No. 2. To date, no literature information has been found on the biological effectiveness of compound no. 2.
Table I Compound Dosage Inhibition of (corresponds to the number) [mg / kg] (i.p.) ulcers [%] of example 1 20 100 2 20 91 3 20 80 4 20 100 5 20 43 6 20 86
The present invention is described in more detail by the following examples.
example 1
A solution of 5.0 g of 2,4-dichloro-6- (2,5-dichlorophenyl) s-triazine (melting point 133-134 C) in 100 ml of dioxane is mixed with 20 ml of 28% aqueous ammonia and in a closed tube heated to 100 ° C for 1 hour. After cooling, the reaction mixture is evaporated to dryness under reduced pressure and water is added to the residue. The precipitated crystals are filtered off, washed with water and recrystallized from ethanol, with 4.2 g of 2, 4-diamino-6- (2,5-dichlorophenyl) -s-triazine, m.p.
270-271 "C.
Elemental analysis:
Calculated: C 42.21 H 2.76 N 27.35
Found: C 42.22 H 2.58 N 27.50
Example 2
A solution of 4.3 g of 2,4-dichloro-6- (3, 4-dichlorophenyl) s-triazine (melting point 146-148 ° C.) in 200 ml of methanol, saturated with gaseous ammonia, is kept in a closed tube for one hour heated for a long time at 100 ° C. The reaction mixture is worked up as in Example 1 and the separated crystals are recrystallized from methanol, with 3.8 g of 2,4-diamino6- (3,4-dichlorophenyl) -s-triazine, melting point 230- 232 C.
Elemental analysis:
Calculated: C 42.21 H 2.76 N 27.35
Found: C 42.06 H 2.80 N 27.41
Example 3
A solution of 5.0 g of 2,4-dichloro-6- (3,5-dichlorophenyl) - s-triazine (melting point 151-154 "C) in 100 ml of dioxane is mixed with 20 ml of 28% strength aqueous ammonia and heated to 100 ° C for 1 hour in a closed tube. The reaction mixture is worked up as in Example 1 and the separated crystals are recrystallized from dioxane, 4.4 g of 2,4-diamino-6- (3,5-dichlorophenyl) -s-triazine, melting point above 3000 ° C., being obtained.
Elemental analysis:
Calculated: C 42.21 H 2.76 N 27.35
Found: C 42.56 H 2.49 N 27.50
Example 4
A solution of 3.9 g of 2,4-dichloro-6- (2,4-dichlorophenyl) s-triazine (melting point 115-117 C) in 100 ml of ethanol is mixed with 20 ml of 28% aqueous ammonia and in a closed tube heated for 1 hour at 100 ° C. The reaction mixture is worked up as in Example 1 and the separated crystals are recrystallized from acetone, with 3.3 g of 2,4-diamino-6- (2,4-dichlorophenyl) -s -triazine, m.p. 205-207 ° C., can be obtained.
Elemental analysis:
Calculated: C 42.21 H 2.76 N 27.35
Found: C 42.41 H 2.70 N 27.02
Example 5
A solution of 2.1 g of 2,4-dichloro-6- (2,5-dibromophenyl) s-triazine (melting point of the crude crystals 160-168 C) in 50 ml of dioxane is mixed with 10 ml of 28% ammonia and heated for 1 hour at 100 ° C. The reaction mixture is worked up as in Example 1 and the separated crystals are recrystallized from dioxane, 1.2 g of 2,4-diamino-6 (2,5-dibromophenyl) -s-triazine, mp 272-274C.
Elemental analysis:
Calculated: C 31.33 H 2.05 N 20.30
Found: C 31.53 H 1.92 N 20.45
Example 6
A solution of 1.0 g of 2,4-dichloro-6- (2-chloro-5-bromophenyl) -s-triazine (melting point of the crude crystals 140-145 C) in 30 ml of dioxane is mixed with 5 ml of 28% aqueous ammonia and heated for one hour at 100 ° C. The reaction mixture is worked up as in Example 1 and the separated crystals are recrystallized from a mixture of dioxane and ethanol, with 0.52 g of 2,4-diamino-6 (2-chloro -5-bromophenyl) -s-triazine, m.p. 280-282 "C, can be obtained.
Elemental analysis:
Calculated: C 35.97 H 2.35 N 23.30
Found: C 36.01 H 2.34 N 23.19
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14660274A JPS554752B2 (en) | 1974-12-19 | 1974-12-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH596193A5 true CH596193A5 (en) | 1978-03-15 |
Family
ID=15411424
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1652175A CH596193A5 (en) | 1974-12-19 | 1975-12-19 | Dihalobenzoguanamines with anti-ulcus activity |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JPS554752B2 (en) |
| AT (1) | AT343668B (en) |
| CH (1) | CH596193A5 (en) |
| NL (1) | NL156696B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4541809B2 (en) * | 2004-09-08 | 2010-09-08 | キヤノン株式会社 | Organic compound and organic light emitting device |
| US10474050B2 (en) | 2015-09-17 | 2019-11-12 | Hodogaya Chemical Co., Ltd. | Toner and charge control agent using pyrazolone derivative or salt of derivative |
| JP2017160144A (en) * | 2016-03-08 | 2017-09-14 | 東ソー株式会社 | 4,6-dichlorotriazine compound and method of producing the same |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4969688A (en) * | 1972-11-02 | 1974-07-05 |
-
1974
- 1974-12-19 JP JP14660274A patent/JPS554752B2/ja not_active Expired
-
1975
- 1975-12-03 NL NL7514062.A patent/NL156696B/en not_active IP Right Cessation
- 1975-12-18 AT AT963175A patent/AT343668B/en not_active IP Right Cessation
- 1975-12-19 CH CH1652175A patent/CH596193A5/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5175083A (en) | 1976-06-29 |
| ATA963175A (en) | 1977-10-15 |
| NL7514062A (en) | 1976-06-22 |
| AT343668B (en) | 1978-06-12 |
| NL156696B (en) | 1978-05-16 |
| JPS554752B2 (en) | 1980-01-31 |
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