DE279193C - - Google Patents
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- Publication number
- DE279193C DE279193C DENDAT279193D DE279193DA DE279193C DE 279193 C DE279193 C DE 279193C DE NDAT279193 D DENDAT279193 D DE NDAT279193D DE 279193D A DE279193D A DE 279193DA DE 279193 C DE279193 C DE 279193C
- Authority
- DE
- Germany
- Prior art keywords
- parts
- hydrogen
- percent
- hydrochloric acid
- aminomethylquinoline
- 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.)
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- 150000002825 nitriles Chemical class 0.000 claims description 4
- 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 23
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 10
- 239000001257 hydrogen Substances 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 5
- 229910052763 palladium Inorganic materials 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- JBSAUEMFOKUWTP-UHFFFAOYSA-N quinoline-4-carbonitrile Chemical compound C1=CC=C2C(C#N)=CC=NC2=C1 JBSAUEMFOKUWTP-UHFFFAOYSA-N 0.000 description 4
- 229960000583 Acetic Acid Drugs 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating Effects 0.000 description 3
- 239000012295 chemical reaction liquid Substances 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- SMWDFEZZVXVKRB-UHFFFAOYSA-N quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 3
- 150000003248 quinolines Chemical class 0.000 description 3
- 239000003513 alkali Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- HGHPGHVNTQSTNM-UHFFFAOYSA-N quinolin-2-ylmethanamine Chemical compound C1=CC=CC2=NC(CN)=CC=C21 HGHPGHVNTQSTNM-UHFFFAOYSA-N 0.000 description 2
- BVQGQPVMVBOTID-UHFFFAOYSA-N quinolin-4-ylmethanamine Chemical compound C1=CC=C2C(CN)=CC=NC2=C1 BVQGQPVMVBOTID-UHFFFAOYSA-N 0.000 description 2
- WDXARTMCIRVMAE-UHFFFAOYSA-N quinoline-2-carbonitrile Chemical class C1=CC=CC2=NC(C#N)=CC=C21 WDXARTMCIRVMAE-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000003638 reducing agent Substances 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- FNLVEUOYGPHYAK-UHFFFAOYSA-N 6-ethoxyquinoline-4-carbonitrile Chemical compound N1=CC=C(C#N)C2=CC(OCC)=CC=C21 FNLVEUOYGPHYAK-UHFFFAOYSA-N 0.000 description 1
- HWZUVHWTAXHZHG-UHFFFAOYSA-N 6-methoxyquinoline-4-carbonitrile Chemical compound N1=CC=C(C#N)C2=CC(OC)=CC=C21 HWZUVHWTAXHZHG-UHFFFAOYSA-N 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 241000978776 Senegalia senegal Species 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 230000001476 alcoholic Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000006286 aqueous extract Substances 0.000 description 1
- 125000004429 atoms Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000005044 dihydroquinolinyl group Chemical group N1(CC=CC2=CC=CC=C12)* 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 210000000056 organs Anatomy 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- -1 quinaldinic acid nitrile Chemical class 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003530 tetrahydroquinolines Chemical class 0.000 description 1
- 230000001225 therapeutic Effects 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
- C07D215/20—Oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Quinoline Compounds (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
Amine der allgemeinen Formel R
in der R den Rest des Chinolins oder eines substituierten Chinolins bedeutet, sind bisher
nicht zugänglich gewesen. Sie entstehen, wie gefunden wurde, bei der Reduktion von Nitrilen
der Chinolinreihe nach den üblichen Methoden. Amines of the general formula R
in which R denotes the remainder of the quinoline or a substituted quinoline have not yet been available. As has been found, they arise from the reduction of nitriles of the quinoline series by the usual methods.
Bei der leichten Reduzierbarkeit der Methingruppen. im Pyridinrest des Chinolinmoleküls ließ sich nicht ohne weiteres voraussehen, daß die Reduktion bei der Bildung der co-Aminomethylchinoline stehenbleiben würde. Bekanntlich (vgl. Richter, Organ. Chemie ii. Aufl., Bd. II [1913], S. 883 letzter Absatz; Ber. 41, S. 2702 [1908], und Ber. 44, S. 2106 [1911]) lagern Substitutionsprodukte des Chinolins unter der Einwirkung von bestimmten sauren oder alkalischen Reduktionsmitteln zwei oder vier Wasserstoffatome an den Pyridinkern an, wobei sogenannte Dihydrochinoline, bimolekulare Verbindungen von noch nicht aufgeklärter Konstitution oder Tetrahydrochinoline entstehen.With the ease with which the methine groups can be reduced. in the pyridine residue of the quinoline molecule It was not easy to foresee that the reduction would result in the formation of the co-aminomethylquinoline would remain. As is well known (cf. Richter, Organ. Chemie ii. Aufl., Vol. II [1913], p. 883 last paragraph; Ber. 41, p. 2702 [1908], and Ber. 44, p. 2106 [1911]) store substitution products of quinoline under the action of certain acidic or alkaline reducing agents two or four hydrogen atoms on the pyridine nucleus, so-called dihydroquinolines, bimolecular compounds of as yet unexplained constitution or tetrahydroquinolines develop.
Die folgenden Versuche lehren, daß bei Cyanchinolinen die Reduktion leichter in der Seitenkette am Cyanrest als am Chinolinkern erfolgt. Bei Verwendung von Palladiumsol und molekularem Wasserstoff geht 4-Cyanchinolin so gut wie quantitativ in 4-uj-Aminomethylchinolin (Lepidylamin) über. Auch saure, Wasserstoff entwickelnde Reduktionsmittel lassen sich verwenden; es ist nur notwendig, die Reaktion bei nicht zu hohen Temperaturen vorzunehmen und sie zum geeigneten Zeitpunkt zu unterbrechen.The following experiments teach that the reduction in cyanoquinolines is easier in the Side chain occurs on the cyano residue than on the quinoline nucleus. When using palladium sol and molecular hydrogen, 4-cyanoquinoline goes almost quantitatively to 4-uj-aminomethylquinoline (Lepidylamine) about. Acidic reducing agents which generate hydrogen can also be used; it is only necessary carry out the reaction at temperatures that are not too high and interrupt it at the appropriate time.
In eine Auflösung von 50 Teilen 4-Cyanchinolin in 1250 Teilen verdünnter Salzsäure (enthaltend 2V2 Mol. HCl auf 1 Mol. Nitril) wird bei Gegenwart von kolloidalem Palladium Wasserstoff unter einem Überdruck von Vio Atm. eingepreßt. Nach Absorption des berechneten Volumens Wasserstoff engt man die vom Palladium befreite Reaktionsflüssigkeit stark ein, wobei ein saures Chlorhydrat des 4-Aminornethylchinolins:In a dissolution of 50 parts of 4-cyanquinoline in 1250 parts of dilute hydrochloric acid (containing 2V 2 mol. HCl to 1 mol. Nitrile), in the presence of colloidal palladium, hydrogen is generated under an excess pressure of one hundred atm. pressed in. After the calculated volume of hydrogen has been absorbed, the reaction liquid from which the palladium has been removed is strongly concentrated, an acidic chlorohydrate of 4-amino methylquinoline:
CH9-NH9 CH 9 -NH 9
in weißen Nadeln ausfällt. Dieses Salz ist in Wasser sehr leicht, in Alkohol sehr schwer löslich. Die hieraus in Freiheit gesetzte Basefails in white needles. This salt is very light in water and very heavy in alcohol soluble. The base set free from this
bildet ein fast farbloses Öl, das sich an der Luft rasch violett färbt. Es siedet bei 172 ° unter 8 mm Druck.forms an almost colorless oil that quickly turns purple in air. It boils at 172 ° under 8 mm of pressure.
Für: C10H10N2 For: C 10 H 10 N 2
berechnet: gefunden:calculated: found:
■ C = 75,95 Prozent, C = 76,05 Prozent,
H= 6,33 - H= 6,39■ C = 75.95 percent, C = 76.05 percent,
H = 6.33 - H = 6.39
N = 17,72 - N = 17,88 - .N = 17.72 - N = 17.88 -.
Das 4-Aminomethylchinolin, eine starke Base, ist geruchlos, löst sich in Wasser, Alkohol und Äther und ist gegen Sauerstoff empfindlich. Das Monochlorhydrat löst sich sehr leicht in Wasser, schmilzt bei etwa 206 bis 208° und färbt sich an der Luft bläulich.The 4-aminomethylquinoline, a strong base, is odorless, dissolves in water, alcohol and ether and is sensitive to oxygen. The monochlorohydrate dissolves very easily in water, melts at about 206 to 208 ° and turns bluish in air.
Eine Auflösung von 15,4 Teilen 4-Cyanchinolin (1Z10 Mol.) in 100 Teilen heißem Eisessig wird allmählich mit 30 Teilen Zinkstaub versetzt und die lebhafte Reaktion durch gelindes Kühlen gemäßigt. Nach beendeter Einwirkung wird das Aminomethylchinolin durch Schütteln der filtrierten, Flüssigkeit mit Alkali und Äther abgeschieden.A dissolution of 15.4 parts of 4-cyanquinoline ( 1 Z 10 mol.) In 100 parts of hot glacial acetic acid is gradually mixed with 30 parts of zinc dust and the lively reaction is moderated by gentle cooling. After the end of the exposure, the aminomethylquinoline is deposited by shaking the filtered liquid with alkali and ether.
Beispiel III.Example III.
30 Teile 4-Cyanchinolin werden in 250 Teilen konzentrierter Salzsäure gelöst, mit granuliertem Zink versetzt und auf dem Wasserbade erwärmt. Die Reaktionsflüssigkeit wird,-wie unter II angegeben, weiter verarbeitet.30 parts of 4-cyanoquinoline are divided into 250 parts dissolved concentrated hydrochloric acid, mixed with granulated zinc and put on the water bath warmed up. The reaction liquid is processed further as indicated under II.
5 Teile 6-Methoxy-4-Cyanchinolin (Chininsäurenitril) in 200 Teilen Eisessig gelöst und Palladiumsol (bereitet aus 25 Teilen iprozentiger Palladiumchlorürlösung, 25 Teilen Eisessig und 0,6 Teilen Gummi arabicum) werden mit molekularem Wasserstoff wie oben behandelt. Nach Aufnahme des berechneten Volumens Wasserstoff wird mit Salzsäure versetzt und im Vakuum zur Trockne gebracht.5 parts of 6-methoxy-4-cyanoquinoline (quininonitrile) dissolved in 200 parts of glacial acetic acid and Palladium sol (prepared from 25 parts of 1 percent palladium chloride solution, 25 parts of glacial acetic acid and 0.6 parts gum arabic) are treated with molecular hydrogen as above. After recording the calculated Hydrochloric acid is added by volume of hydrogen and the mixture is brought to dryness in vacuo.
Der Rückstand ' wird mit wenig Wasser ausgezogen. Die so erhaltene filtrierte Lösung gibt auf Zusatz von alkoholischer Salzsäure das Dichlorhydrat des 6-Methoxyl-4-(r-aminomethylchinolins: The residue is extracted with a little water. The filtered solution obtained in this way gives, upon addition of alcoholic hydrochloric acid, the dichlorohydrate of 6-methoxyl-4- (r-aminomethylquinoline:
CH2NH2 CH 2 NH 2
CHoO-CHoO-
in weißen verfilzten Nädelchen, welche sich beim Trocknen gelblich färben und unter Zersetzung bei 253° schmelzen.in white matted needles, which turn yellowish on drying and decompose melt at 253 °.
Für: C11H12ON2, 2 HClFor: C 11 H 12 ON 2 , 2 HCl
berechnet: gefunden:calculated: found:
Cl = 27,20 Prozent, Cl = 24,92 Prozent.Cl = 27.20 percent, Cl = 24.92 percent.
Die aus dem Dichlorhydrat in der üblichen Weise gewonnene freie Base stellt ein an der Luft sich violett färbendes Öl dar.The free base obtained from the dichlorohydrate in the usual way represents a Air turns violet into oil.
Eine Lösung von 1 Teil 6-Äthoxy-4-Cyanchinolin und 21Z2 Teilen Chlorwasserstoff in 8oprozentigem Alkohol wird mit elementarem Wasserstoff in Gegenwart von Palladiumschwarz geschüttelt. Sobald das zur Reduktion notwendige Volumen Wasserstoff aufgenommen ist, wird die Reaktionsflüssigkeit nach Entfernung des Palladiums eingeengt. Dabei scheidet sich das Dichlorhydrat des 6-Äthoxy-4"C<j-aminomethylchinolins aus. Nach dem Umkristallisieren aus salzsäurehaltigem Alkohol erhält man feine seidenglänzende schwach gelbliche Nädelchen, welche bei 262 ° unter Zersetzung schmelzen.A solution of 1 part of 6-ethoxy-4-cyanoquinoline and 2 1 Z 2 parts of hydrogen chloride in 8% alcohol is shaken with elemental hydrogen in the presence of palladium black. As soon as the volume of hydrogen required for the reduction has been absorbed, the reaction liquid is concentrated after the palladium has been removed. The dichlorohydrate of 6-ethoxy-4 "C <j-aminomethylquinoline separates out. After recrystallization from alcohol containing hydrochloric acid, fine, silky, pale yellowish needles are obtained which melt at 262 ° with decomposition.
Für: C12H14ON2, 2 HClFor: C 12 H 14 ON 2 , 2 HCl
berechnet: gefunden:calculated: found:
Cl = 25,82 Prozent, Cl = 25,72 Prozent.Cl = 25.82 percent, Cl = 25.72 percent.
Die freie Base ist ein fester Körper und kristallisiert aus Äther in schwach gelbgrünen Nädelchen vom Schmelzpunkt 74°.The free base is a solid body and crystallizes from ether in pale yellow-green Needles with a melting point of 74 °.
Eine Auflösung von 1 Teil 2-Cyanchinolin (Chinaldinsäurenitril) und 21Z2 Teilen Chlor-Wasserstoff in 8oprozentigem Alkohol wird unter Verwendung von Palladiumschwarz und molekularem Wasserstoff reduziert. Nach Aufnahme von 4 Atomen Wasserstoff, auf 1 Molekül Nitril wird das Reaktionsprodukt eingedampft. Der konzentrierte wäßrige Auszug des Rückstands wird sodann mit starker Alkalilauge übersättigt, ausgeäthert und die abgehobene ätherische Lösung mit stark verdünnter Salzsäure bis zur Blaufärbung von Kongopapier behandelt. Die salzsaure Lösung wird nun nach dem Zusatz von überschüssiger Salzsäure bis auf ein geringes Volumen eingeengt. Beim Erkalten scheidet sich das Dichlorhydrat des 2-oi-Aminomethylchinolins (Chinaldylaminsj in ockergelben glänzenden Kristallblättchen ab, welche nach der Umkristallisation aus starkem salzsäurehaltigen Alkohol bei 245 bis 246 ° unter Zersetzung schmelzen.A dissolution of 1 part of 2-cyanquinoline (quinaldinic acid nitrile) and 2 1 2 parts of chlorine-hydrogen in 8% alcohol is reduced using palladium black and molecular hydrogen. After 4 atoms of hydrogen have been absorbed for 1 molecule of nitrile, the reaction product is evaporated. The concentrated aqueous extract of the residue is then supersaturated with strong alkali lye, extracted with ether and the ethereal solution removed is treated with very dilute hydrochloric acid until the Congo paper turns blue. The hydrochloric acid solution is then concentrated to a small volume after the addition of excess hydrochloric acid. When it cools, the dichlorohydrate of 2-oi-aminomethylquinoline (quinaldylamine) separates out in shiny yellow ocher crystal flakes, which, after recrystallization from strong alcohol containing hydrochloric acid, melt with decomposition at 245 to 246 °.
Für: C10H10N2, 2 HClFor: C 10 H 10 N 2 , 2 HCl
berechnet: gefunden:calculated: found:
Cl = 30,73 Prozent, Cl = 30,54 Prozent.Cl = 30.73 percent, Cl = 30.54 percent.
Durch Versetzen des Dichlorhydrats mit Al-By treating the dichlorohydrate with Al-
kali und Ausäthern erhält man das 2-Aminomethylchinolin Potash and ether give 2-aminomethylquinoline
-CH2-NH2 -CH 2 -NH 2
als gelblich gefärbtes Öl.as a yellowish colored oil.
Die ω-Aminomethylchinoline sollen für therapeutische Zwecke und zur Darstellung pharmazeutischer Produkte dienen.The ω-aminomethylquinolines are said to be used for therapeutic Purpose and for the representation of pharmaceutical products.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE279193C true DE279193C (en) |
Family
ID=535129
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT279193D Active DE279193C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE279193C (en) |
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