DE374291C - Process for the preparation of amino substitution products of the pyridine and quinoline series - Google Patents

Process for the preparation of amino substitution products of the pyridine and quinoline series

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Publication number
DE374291C
DE374291C DET19585D DET0019585D DE374291C DE 374291 C DE374291 C DE 374291C DE T19585 D DET19585 D DE T19585D DE T0019585 D DET0019585 D DE T0019585D DE 374291 C DE374291 C DE 374291C
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pyridine
substitution products
preparation
sodium
quinoline
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DET19585D
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German (de)
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ALEXEI EWGENJEWITSCH TSCHITSCH
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ALEXEI EWGENJEWITSCH TSCHITSCH
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen 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
    • C07D213/72—Nitrogen atoms
    • C07D213/73—Unsubstituted amino or imino radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen 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
    • C07D213/72—Nitrogen atoms
    • C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals

Description

Verfahren zur Darstellung von Aminosubstitutionsprodukten der Pyridin- und Chinolinreihe. Das vorliegende Verfahren besteht darin, daß man Pyridin, Chinolin, deren Homologe. oder Substitutionsprodukte oder andere, den Pyridinring enthaltende synthetische oder natürlich vorkommende organische Basen, wie Alkaloide, für sich oder in Gegenwart indiffe- renter organischerLösungsmittel 1nitNatriurn- amnd bzw. mit Aminnatriumverbindungen der allgemeinen .Formel R # NH - Na (R-Aryl, Alkyl oder _eterocyklischer Basenrest) oder Gemischen aus metallischem Natrium und primärem Amin erhitzt. Nach dem Behan- deln der erhaltenen Produkte mit Wasser werden -die gebildeten Aminoverbimlungen durch Destillation oder nach anderen üblichen Methoden gereinigt. Die Reaktion verläuft im Sinne der folgen- den Gleichungen: 1. C, H:-, N -j- Na - N H= - C; H4 N # N il'-,\T a + H_, II. C5H@N # NHNa + H@O - C:G H4 N # :N H_ + N a OH. Dabei bilden sich hauptsächlich die in o-Stellung zum Pyridinstickstoff substituier- ten-Amine, in einigen Fällen auch die 4-Arni- nosubstitutionsprodukte. Auch Diaminosubstitutionsprodukte des Pyridins und analoger Basen lassen sich nach dem Verfahren gewinnen. Bei Verwendung von -Substitutionsprodukten - des. Natrium- amids erhält man sekundäre Amine nach der Gleichung: I. C3H,N #NH#Na ,-' C;H_N = (Ct;H.,N)=' @T@Ta -f- H=, 11. (C;H,N)"N Na -; H., O -NaOH-;- tC;H,N)_#hH. Beispiel r. Trockenes Pvridin wird mit dem gleichen Volumen trockenen Toluols vermischt und dann die der halben, Gewichtsmenge der Base entsprechende Menge sorgfältigst unter An- feuchten mit trockenem Toluol zerriebene Natriumamid zugesetzt. Das Reaktions- gemisch wird dann am Rückf1ußkiihler ; bis 7 Stunden im Ölbade gekocht. wobei die T etn- peratur des Bades zwischen i2o bis i 5o' ge- halten wird. Dann wird zum abgekühlten Produkt Wasser in kleinen 'Mengen unter Umschütteln zugesetzt, wobei Bildung von zwei flüssigen Schichten stattfindet. Nach dem Trocknen der öligen Schicht mit Calciumcar- honat wird sie fraktioniert. Die zwischen Zoo bis 210' siedende Fraktion enthält fast völlig reines 2-Aminopyridin vom Schmelzpunkt 56°. Beispiel Unter gleichen. Bedingungen erhält man aus 2--'llethylpyridin («-Picolin) das bei 2o8 bis 2o9° siedende 6-Aniii:o-2-nietlivlp3-ri(lin vom Scllnielzhtnllct 3().;`. Die Base ist stark li_v- grockopisch 1)l-. l zertließt an der Luft. Beispiel3. 42 Teile (-'liiilolin. 8o Teiie T0',u.li tui.l io Teile Natriumamid werden 5 Stunden im Ülbade auf 12o bis i4o= erwärmt. Nach der oben für (las Pvridin beschriebenen 13c-Iian(1- ltin, wird Glas Pro-lukt unter vermindertem Druck fraktioniert, wobei die unterhalb Zoo` unter 2o uiin Druck siedende Frakticn rohes 2-Aniinochinolin enthält. «-elches (furch Um- kristallisieren aus heißem Wasser in reinem Zustande (Blättchen vom Schmelzpunkt 12d-) erhalten werden kann. Die Ausbeute beträgt etwa 2o bis =; Prozent (ier theoretischen (v.). auch B e i 1 s t e i n , 3. Aufl., Bd. IV, S. 9-o8). Beispiel:. 5o Teile Pyridin. ioo Teile trockenes Vaselinöl und' So Teile sorgfältig zerriebenes Natriumamid werden miteinander vermischt und etwa 15 Stunden erhitzt, wobei die Tem- peratur des Bades erst bis 125' und nach 5 Stunden auf i8o' gehalten wird. Das er- kaltete Produkt wird mit kaltem Wasser be- handelt, dabei kristallisiert das rohe 2,6-Di- aminopyridin aus, welches abgesogen und durch Umkristallisieren aus heißem Benzol bereinigt wird. Die Ausbeute beträgt 5o bis 6o Prozent der theoretischen. Das reine 2.6-Diaminopyridin bildet bei 121.5° schmel- zende Blättchen (vgl. auch Monatshefte für Chemie, Bd. 35, S. 20; (191a)). Beispiel 5. Das nach T h i t h e r 1 e v aus Natriumamid und Anilin dargestellte Anilinnatrium CBH:;NH # Na wird mit gleichem Volumen Pyridin 18 Stun- den lang erwärmt, wobei die Temperatur des Bades allmählich von 15o' bis auf 25o° er- höht wird. Nach dem Behandeln mit Wasser, wie in den vorbeschriebenen Beispielen, wird das Produkt erst unter gewöhnlichem Druck und der höher siedende Rest unter vermin- dertem Druck fraktioniert. Die hochsiedende Fraktion scheidet beim Umkristallisieren aus einem Gemisch von Benzol und Ligroin kleine Kristalle des von O. F i s c h e r dargestellten 2-Phenylaminopyridins vom Schmelzpunkt io8° aus (vgl. Berichte der chem. Ges. 32 (18991, S. 1302; 35 119-021, S. 3675)- 13eis1) ie1 6.Process for the preparation of amino substitution products of the pyridine and quinoline series. The present procedure consists in: that one pyridine, quinoline, their homologues. or substitution products or other den Synthetic or pyridine ring containing naturally occurring organic bases such as Alkaloids, by themselves or in the presence of indifferent renter organic solvent 1nitnatriurn- amnd or with amine sodium compounds of general formula R # NH - Na (R-Aryl, Alkyl or heterocyclic base radical) or Mixtures of metallic sodium and primary amine heated. After treatment deln the products obtained with water - the amino compounds formed by distillation or other customary Methods cleaned. The reaction proceeds in the sense of the following the equations: 1. C, H: -, N -j- Na - NH = - C; H4 N # N il '-, \ T a + H_, II. C5H @ N # NHNa + H @ O - C: G H4 N #: N H_ + N a OH. The in o-position to the pyridine nitrogen substitute ten-amines, in some cases also the 4-arni- nosubstitution products. Also diamino substitution products of Pyridines and analogous bases can be traced win the process. Using of substitution products of sodium amides, secondary amines are obtained after Equation: I. C3H, N # NH # Na, - 'C; H_N = (C t; H., N) = '@ T @ Ta -f- H =, 1 1. (C; H, N) "N Na -; H., O -NaOH -; - tC; H, N) _ # hH. Example r. Dry pvridine is made with the same Volume of dry toluene mixed and then half the weight of the base corresponding amount carefully under wet grated with dry toluene Sodium amide added. The reaction mixture is then at the reflux cooler; until Cooked in an oil bath for 7 hours. where the t temperature of the bath between i2o to i 5o ' will hold. Then it is cooled down Product taking water in small 'amounts Shake added, with formation of two liquid layers takes place. After this Dry the oily layer with calcium car- honat it will be fractionated. The one between the zoo the fraction that boils up to 210 'contains almost all of it pure 2-aminopyridine with a melting point of 56 °. example Under equals. Conditions are obtained from 2 - 'llethylpyridin («-Picolin) that at 208 to 2o9 ° boiling 6-aniii: o-2-nietlivlp3-ri (lin from Scllnielzhtnllct 3 () .; `. The base is strong li_v- grockopically 1) l-. l freezes in the air. Example3. 42 parts (-'liiilolin. 8o part T0 ', u.li tui.l 10 parts of sodium amide are im Ülbade to 12o to 14o = warmed up. After above for (read pvridine described 13c-Iian (1- ltin, glass pro-luct is under diminished Fractional printing, with the one below Zoo` raw fracture boiling under pressure Contains 2-aniinoquinoline. «-Which (for crystallize from hot water in pure Conditions (leaflets with a melting point of 12d-) can be obtained. The yield is about 2o to =; Percent (ier theoretical (v.). also B ei 1stein, 3rd ed., Vol. IV, pp. 9-08). Example:. 50 parts of pyridine. ioo parts dry Vaseline oil and 'so parts carefully grated Sodium amide are mixed together and heated for about 15 hours, the tem- temperature of the bath only up to 125 'and after Is held at i8o 'for 5 hours. The cold product is loaded with cold water acts, the crude 2,6-di- aminopyridine from which sucked off and by recrystallization from hot benzene is adjusted. The yield is 50 to 6o percent of the theoretical. The pure At 121.5 °, 2,6-diaminopyridine forms zende papers (see also monthly booklets for Chemie, Vol. 35, p. 20; (191a)). Example 5. That after T hither 1 ev from sodium amide and aniline sodium represented by aniline CBH:; NH # Na is used with the same volume of pyridine for 18 hours the heated for a long time, the temperature of the Bath gradually from 15o ' to 25o ° is raised. After treating with water, as in the examples described above the product only under normal pressure and the higher-boiling residue under reduced that pressure is fractionated. The high-boiling one Fraction separates out during recrystallization a mixture of benzene and ligroin small Crystals of the depicted by O. F ischer 2-phenylaminopyridines from the melting point io8 ° from (see reports of the chem. Ges. 32 (18991, p. 13 0 2; 35 119- 0 21, p. 3675) - 13eis1) ie1 6.

Bei #ler I?inwirkun,@ vc@n Pvri(Ivlnatrituiiainid (aus 2-Aminopyridin und metallischem Natrium erhalten) auf I'vri,lin oder von i Jlol. Natriumainid auf 2 \)o1. Pvri(lin in Vase'inül bei 200 bis 2;0- während i ; Stunden erhält inan eine unter einem Druck von 16 mm bei etwa 200' siedende Fraktion, die aus heißem Wasser in Form von in Äther leichtlöslichen Nädelchen kristallisiert, welche bei 95° (stabile Form) oder hei 86 bis 8;° (labile Form) schmelzen. Diese Verbindung ist das 2,2'-Dipyridvlamin.If you have an effect, @ vc @ n Pvri (Ivlnatrituiiainid (from 2-aminopyridine and metallic sodium) on I'vri, lin or from i Jlol. Sodium ainide 2 \) o1. Pvri (lin in vase'inül at 200 to 2; 0- for 1; hours receives inan under a pressure of 16 mm at about 200 'boiling fraction consisting of hot water crystallized in the form of needles, easily soluble in ether, which at 95 ° (stable Shape) or hot 86 to 8; ° (labile shape) melt. This compound is the 2,2'-dipyridylamine.

Beispiel 23 Teile N icotin. 6..1 Teile latritunami(1 und 25 Teile Toluol werden 3o Stunden auf 120 bis 140' erhitzt. Das Prcaukt wird mit heißem Wasser behandelt, die ölige Schicht mit Salzsäure extrahiert und dann die sauere Lösung der Basen mit Kalilauge zersetzt..Die ausgeschiedenen Basen werden unter vermindertem Druck fraktioniert. Die enter 15 min Druck zn-ischen 1;o bis i85° übergegangene Fraktion scheidet beim Erkalten Kristalle aus, «-elche nach dem Umkristallisieren aus heißem Ligroin weiße@ristallaggregate voinSchmelzpunkt 125 bis 126° bilden. Die Verbindung gab bei der Analyse auf die Formei " CioH#T H.Example 23 parts of nicotine. 6..1 parts latritunami (1 and 25 parts Toluene are heated to 120 to 140 ° for 30 hours. The prcaukt is made with hot water treated, the oily layer extracted with hydrochloric acid and then the acidic solution the bases are decomposed with potassium hydroxide solution. The precipitated bases are reduced under reduced Fractional printing. Enter 15 min of pressure at 1; 0 to 185 ° The fraction separates out crystals when it cools down, "-elche after recrystallization Form white crystalline aggregates from hot ligroin with a melting point of 125 to 126 °. When analyzed, the compound gave the formula "CioH # T H.

stimmende Zahlen und ist das noch unbekannte Aminonicotin.correct numbers and is the still unknown aminonicotine.

Auch andere den Pv ridinring enthaltende Alkaloide, z. B. Cinchonin, lassen sich durch Einwirkung von Natriumamid in Aminosubstitutionsprodukte überführen.Other alkaloids containing the PVC ring, e.g. B. cinchonine, can be converted into amino substitution products by the action of sodium amide.

Beispiel 8. -Beim Erwärmen von i i Teilen des \ atriumsalzes des 2-Oxypyridins mit 4 Teilen Natriumamid und 2o Teilen Vaselinöl findet bei Zoo bis 25o° eine Reaktion unter Wasserstoffentwicklung statt. Das Vaselinöl wird abgegossen und der in Öl ungelöst gebliebene Rückstand mit Wasser zersetzt. Nach dem Sättigen. der wäßrigen Lösung mit Kohlensäure wird -sie eingedampft und der Rest mit Alkohol extrahiert. Das nach Abdampfen des Alkohols-Verbleibende stellt das rohe 6 Amino-2-oxypyridin vor.Example 8. -When heating i i parts of the atrium salt of 2-oxypyridine With 4 parts of sodium amide and 2o parts of vaseline oil, a reaction occurs at Zoo up to 25o ° takes place with evolution of hydrogen. The vaseline oil is poured off and the one in oil undissolved residue is decomposed with water. After satiety. the aqueous Carbonated solution is evaporated and the remainder extracted with alcohol. What remains after evaporation of the alcohol is the crude 6-amino-2-oxypyridine before.

Die nach dem vorliegenden Verfahren erhältlichen Amine finden zu den verschiedenartigsten Zwecken gewerbliche Verwertung: so i. als pharmazeutische Präparate. Wie z. B. C o m p s fand (Archiv der Pharmazie, Bd. 2.40, S. 3.t7)", besitzt das 2-Aminopyridin cocainähnliche Eigenschaften. Das Aminonicotin ist ein starkes Gift; 2. als Ausgangsstoffe zur Darstellung von Farbstoffen. Das 2,6-Diaminopyridin läßt sich z. B. mit aromatischen Diazoverbindungen leicht zu Azofarbstoffen kuppeln. Außerdem ist gefunden worden, .daß Afninopyri-dine sich leicht nitrieren lassen. Beim Nitrieren des Aminopyridins werden so isomere Nitroanl.inopyridine erhalten: nämlich das 2-Amino-5-nitropyridin, gelbe Blättchen vom Schmelzpunkt r88° und Idas 2-Amino-3-nitropyridin, gelbe Nadeln vom Schmelzpunkt 164.°. Die an erster Stelle angeführte Nitroverbindung kann leicht zum 2,5-Diaminopyridin reduziert werden (vgl. auch H. M e y e r und F. S t a f -f e n, Chem. Zentralbl. 1913, I, S. 182I), aus welchem ebenfalls Farbstoffe erhalten werden, die analoge Eigenschaften raufweisen wie die unter Verwendung von p-Phenylendiamin er= hältlichen Farbstoffe; 3. Diamine vom Typus und Aminooxypyridine vom Typus können zur Herstellung von photographischen Entwicklern @"erwendung finden.The amines obtainable by the present process are used commercially for a wide variety of purposes: see above i. as pharmaceutical preparations. Such as B. Comps found (Archiv der Pharmazie, Vol. 2.40, p. 3.t7) ", the 2-aminopyridine has cocaine-like properties. The aminonicotin is a strong poison; 2. As a starting material for the preparation of dyes. The 2.6 Diaminopyridine can, for example, easily be coupled with aromatic diazo compounds to form azo dyes. Furthermore, it has been found that afninopyridines can be easily nitrated. When aminopyridine is nitrated, isomeric nitroan.inopyridines are obtained: namely 2-amino-5 -nitropyridine, yellow leaflets with a melting point of 88 ° and idas 2-amino-3-nitropyridine, yellow needles with a melting point of 164 °. The nitro compound listed first can easily be reduced to 2,5-diaminopyridine (cf. also H. M eyer and F. S taffen, Chem. Zentralbl. 1913, I, p. 182I), from which dyes are also obtained which have properties analogous to those obtainable using p-phenylenediamine; 3. Diamine from type and aminooxypyridines of the type can be used for the production of photographic developers.

Claims (1)

PATENT-ANSPRUCII: Verfahren zur Darstellung von Aminosubstitutionsprodukten der Pyridin- und Chinolinreihe, darin bestehend, daß man Pyridin, Chinolin, deren Homologe oder Substitutionsprodukte oder andere, den Pyridinring enthaltende synthetische oder natürlich vorkommende organische Basen (Alkaloide) für sich oder in Gegenwart indifferenter organischer Lösungsmittel mit Natriumamid bzw. mit Aminnatriumverbindungen der allgemeinen Formel R - NH - Na (R - Aryl, Alkyl oder heterocyklischer Basenrest, wie Pyriidyl oder Chinolyl) oder Gemischen aus metallischem Natrium und primärem Amin erhitzt.PATENT-ANSPRUCII: Process for the preparation of amino substitution products the pyridine and quinoline series, consisting in that one pyridine, quinoline, their Homologous or substitution products or other synthetic ones containing the pyridine ring or naturally occurring organic bases (alkaloids) on their own or in the presence Indifferent organic solvent with sodium amide or with amine sodium compounds of the general formula R - NH - Na (R - aryl, alkyl or heterocyclic base residue, such as pyriidyl or quinolyl) or mixtures of metallic sodium and primary Amine heated.
DET19585D 1914-03-24 1914-03-24 Process for the preparation of amino substitution products of the pyridine and quinoline series Expired DE374291C (en)

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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2531756A (en) * 1949-07-02 1950-11-28 American Cyanamid Co Turkey blackhead control composition
DE1119274B (en) * 1954-03-19 1961-12-14 Raschig Gmbh Dr F Process for the preparation of 2-amino-4-alkyl-pyridines
EP2228366A1 (en) 2009-03-12 2010-09-15 Archimica GmbH Method for producing 2-amino-4-(halogenalkyl)pyridine derivatives by means of cyclization of suitable nitrile precursors with nitrogen combinations
DE102009012471A1 (en) 2009-03-12 2010-09-16 Archimica Gmbh Preparing a 2-amino pyridine derivative comprises reacting an open-chain nitrile precursor with a nitrogen containing compound in a cyclization reaction
DE102009016374A1 (en) 2009-04-07 2010-10-14 Archimica Gmbh Preparing a 2-amino pyridine derivative comprises reacting an open-chain nitrile precursor with a nitrogen containing compound in a cyclization reaction
FR2983196A1 (en) * 2008-01-10 2013-05-31 Centre Nat Rech Scient INHIBITORY CHEMICAL MOLECULES IN THE SPLICE MECHANISM FOR TREATING DISEASES RESULTING FROM SPLICE ANOMALIES.
US9890112B2 (en) 2011-04-01 2018-02-13 Abivax Compounds for use as therapeutic agents affecting p53 expression and/or activity

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2531756A (en) * 1949-07-02 1950-11-28 American Cyanamid Co Turkey blackhead control composition
DE1119274B (en) * 1954-03-19 1961-12-14 Raschig Gmbh Dr F Process for the preparation of 2-amino-4-alkyl-pyridines
FR2983196A1 (en) * 2008-01-10 2013-05-31 Centre Nat Rech Scient INHIBITORY CHEMICAL MOLECULES IN THE SPLICE MECHANISM FOR TREATING DISEASES RESULTING FROM SPLICE ANOMALIES.
US9233931B2 (en) 2008-01-10 2016-01-12 Centre Nationale De Recherche Scientifique Chemical molecules that inhibit the slicing mechanism for treating diseases resulting from splicing anomalies
US10130595B2 (en) 2008-01-10 2018-11-20 Centre Nationale De Recherche Scientifique Chemical molecules that inhibit the slicing mechanism for treating diseases resulting from splicing anomalies
US10654813B2 (en) 2008-01-10 2020-05-19 Centre National De La Recherche Scientifique Chemical molecules that inhibit the slicing mechanism for treating diseases resulting from splicing anomalies
EP2228366A1 (en) 2009-03-12 2010-09-15 Archimica GmbH Method for producing 2-amino-4-(halogenalkyl)pyridine derivatives by means of cyclization of suitable nitrile precursors with nitrogen combinations
DE102009012471A1 (en) 2009-03-12 2010-09-16 Archimica Gmbh Preparing a 2-amino pyridine derivative comprises reacting an open-chain nitrile precursor with a nitrogen containing compound in a cyclization reaction
DE102009016374A1 (en) 2009-04-07 2010-10-14 Archimica Gmbh Preparing a 2-amino pyridine derivative comprises reacting an open-chain nitrile precursor with a nitrogen containing compound in a cyclization reaction
US9890112B2 (en) 2011-04-01 2018-02-13 Abivax Compounds for use as therapeutic agents affecting p53 expression and/or activity
US10538485B2 (en) 2011-04-01 2020-01-21 Abivax Compounds for use as therapeutic agents affecting P53 expression and/or activity

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