DD248593A1 - PROCESS FOR PREPARING 4-BASED SUBSTITUTED THIENO / 2,3-D / PYRIMIDIN-6-YLCARBOXYANESEESTERS - Google Patents

PROCESS FOR PREPARING 4-BASED SUBSTITUTED THIENO / 2,3-D / PYRIMIDIN-6-YLCARBOXYANESEESTERS Download PDF

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DD248593A1
DD248593A1 DD27250685A DD27250685A DD248593A1 DD 248593 A1 DD248593 A1 DD 248593A1 DD 27250685 A DD27250685 A DD 27250685A DD 27250685 A DD27250685 A DD 27250685A DD 248593 A1 DD248593 A1 DD 248593A1
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alkyl
phenyl
general formula
pyrimidin
compounds
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DD27250685A
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German (de)
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Ralf Boehm
Reinhard Pech
Angela Baumgartner
Dieter Lohmann
Gunter Laban
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Univ Halle Wittenberg
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Publication of DD248593A1 publication Critical patent/DD248593A1/en

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Abstract

Die Erfindung betrifft ein Verfahren zur Herstellung von 4-basischsubstituierten Thieno/2,3-d/pyrimidin-6-ylcarbonsaeureesternder allgemeinen Formel I, worin R1, R2 alkyl, R3 H, alkyl, phenyl, R4 alkyl, phenyl, subst. phenyl, aralkyl bedeuten. Diese Verbindungen stellen potentielle Pharmaka dar und sind gleichzeitig Zwischenprodukte der pharmazeutischen Industrie. Ziel der Erfindung ist es, ausgehend von 3,4-Dihydro-4-oxothieno/2,3-d/pyrimidin-6-ylcarbonsaeureestern der allgemeinen Formel II, worin R1, R2 alkyl, R3H, alkyl, phenyl bedeuten, 4-basischsubstituierte Thieno/2,3-d/pyrimidin-6-ylcarbonsaeureester darzustellen. Die Synthese der Verbindungen der allgemeinen Formel I erfolgt durch Umsetzung der Verbindungen der allgemeinen Formel II mit Phosphoroxidchlorid, wobei die anfallenden 4-Chlorderivate der allgemeinen Formel III anschliessend mit einem primaeren Amin in einem polar protischen organischen Loesungsmittel zur Reaktion gebracht werden.The invention relates to a process for the preparation of 4-basic substituted thieno / 2,3-d / pyrimidin-6-ylcarbonsaeureesternder general formula I, wherein R1, R2 alkyl, R3 is H, alkyl, phenyl, R4 alkyl, phenyl, subst. phenyl, aralkyl. These compounds are potential drugs and are also intermediates in the pharmaceutical industry. The aim of the invention is, starting from 3,4-dihydro-4-oxothieno / 2,3-d / pyrimidin-6-ylcarbonsaeureestern of the general formula II, in which R1, R2 alkyl, R3H, alkyl, phenyl mean, 4-basic-substituted Thieno / 2,3-d / pyrimidin-6-ylcarbonsaeureester represent. The synthesis of the compounds of general formula I is carried out by reacting the compounds of general formula II with phosphorus oxychloride, wherein the resulting 4-chloro derivatives of general formula III are subsequently reacted with a primary amine in a polar protic organic solvent.

Description

Hierzu 1 Seite FormelnFor this 1 page formulas

Anwendungsgebiet der ErfindungField of application of the invention

Die Erfindung betrifft ein Verfahren zur Synthese von 4-basischsubstituierten Thieno/2,3-d/pyrimidin-6-yl-carbonsäureestern der allgemeinen Formel I,The invention relates to a process for the synthesis of 4-basic-substituted thieno / 2,3-d / pyrimidin-6-yl-carboxylic acid esters of general formula I,

worin R1, R2 = alkyl,wherein R 1 , R 2 = alkyl,

R3 = H, alkyl, phenyl,R 3 = H, alkyl, phenyl,

R4 = alkyl, phenyl, subst. phenyl, aralkylR 4 = alkyl, phenyl, subst. phenyl, aralkyl

bedeuten.mean.

Die Verbindungen stellen potentielle Pharmaka und gleichzeitig Zwischenprodukte der pharmazeutischen Industrie dar.The compounds are potential drugs and also intermediates of the pharmaceutical industry.

Charakteristik der bekannten technischen LösungenCharacteristic of the known technical solutions

Verbindungen der allgemeinen Formel I werden bisher weder in der Patent- noch in der Fachliteratur beschrieben. Bekannt sind bisher lediglich die 3,4-Dihydro-4-oxothieno/2,3-d/pyrimidine der allgemeinen Formel II. Eine weitere Derivatisierung derartiger Strukturen ist bisher noch nicht vorgenommen worden.Compounds of the general formula I are so far described neither in the patent nor in the specialist literature. So far, only the 3,4-dihydro-4-oxothieno / 2,3-d / pyrimidines of general formula II are known. Further derivatization of such structures has not hitherto been carried out.

Ziel der ErfindungObject of the invention

Ziel der Erfindung ist eine einfache und schnelle Herstellungsmethode für bisher nicht zugängliche 4-basischsubstituierte Thieno/2,3-d/pyrimidin-6-ylcarbonsäureester der allgemeinen Formel I mit gut zugänglichen Ausgangsprodukten, um die Palette potentieller Pharmaka bzw. interessanter Zwischenprodukte zu erweitern.The aim of the invention is a simple and rapid production method for previously inaccessible 4-basic-substituted thieno / 2,3-d / pyrimidin-6-ylcarbonsäureester of the general formula I with readily available starting materials to expand the range of potential drugs or interesting intermediates.

Darlegung des Wesens der ErfindungExplanation of the essence of the invention

Aufgabe der Erfindung ist ein Verfahren zur Synthese von 4-basischsubstituierten Thieno/2,3-d/pyrimidin-6-ylcarbonsäureestern der allgemeinen Formel I, worin R1, R2 = alkyl,The object of the invention is a process for the synthesis of 4-basic-substituted thieno / 2,3-d / pyrimidin-6-ylcarboxylic acid esters of the general formula I in which R 1 , R 2 = alkyl,

R3 = H, alkyl, phenyl,R 3 = H, alkyl, phenyl,

R4 = alkyfc phenyl, subst. phenyl, aralkylR 4 = alkyl phenyl, subst. phenyl, aralkyl

bedeuten.mean.

Erfindungsgemäß wird die Aufgabe dadurch gelöst, daß 2-substituierte 3,4-Dihydro-4-oxothieno/2,3-d/pyrimidin-6-ylcarbonsä'ureester der allgemeinen Formel II, worin R1, R2 = alkyl,According to the invention the object is achieved in that 2-substituted 3,4-dihydro-4-oxothieno / 2,3-d / pyrimidin-6-ylcarbonsä'ureester of the general formula II, wherein R 1 , R 2 = alkyl,

R3 = H, alkyl, phenyl, bedeuten,R 3 = H, alkyl, phenyl,

mit Phosphoroxidchlorid in Gegenwart von N,N-Dimethylanilin in der Siedehitze zu den A-Chlorthieno^^-d/pyrimidin-e-ylcarbonsäureestern umgesetzt werden. Diese 4-Chlorthieno/2,3-d/pyrirnidin-6-ylcarbonsäureester der allgemeinen Formel III, worin R1, R2 = alkyl,be reacted with phosphorus oxychloride in the presence of N, N-dimethylaniline in the boiling heat to the A-Chlorthieno ^^ - d / pyrimidine-e-ylcarbonsäureestern. These 4-chlorothieno / 2,3-d / pyrirnidin-6-ylcarboxylic esters of general formula III, wherein R 1 , R 2 = alkyl,

R3 = H, alkyl, phenyl, bedeuten,R 3 = H, alkyl, phenyl,

werden mit einem primären Amin in einem polar protischen organischen Lösungsmittel in der Siedehitze umgesetzt. Unter diesen Bedingungen wird lediglich das Chloratom in 4-Position gegen eine Aminogruppe ausgetauscht, wobei die 4-aminosubstituiertenare reacted with a primary amine in a polar protic organic solvent at boiling temperature. Under these conditions, only the chlorine atom in the 4-position is replaced by an amino group, with the 4-amino-substituted

Thieno^.S-d/pyrimidin-e-ylcarbonsäureester der allgemeinen Formel I, worin R1, R2, R3 und R4 obige Bedeutung besitzen, gebildetThieno ^ .Sd / pyrimidine-e-ylcarbonsäureester the general formula I, wherein R 1 , R 2 , R 3 and R 4 have the above meaning formed

werden.become.

Die Aufarbeitung der erhaltenen Produkte erfolgt in an sich bekannter Weise.The workup of the resulting products is carried out in a conventional manner.

Ausführungsbeispieleembodiments

Die Erfindung soll nachfolgend an zwei Ausführungsbeispielen erklärt werden:The invention will be explained below with reference to two embodiments:

Beispiel 1example 1

^Chlor-e-methylthieno/a.S-d/pyrimidin-e-ylcarbonsäureethylester, C10H9CIN2O2S (256,7) 0,015 mol S-Methyl-S^-dihydro^-oxothieno^^-d/pyrimidin-ö-ylcarbonsäureethylester, 9 ml Phosphoroxidchlorid und 0,75 ml Ν,Ν-Dimethylanilin werden 14 Stunden unter Rückfluß erhitzt. Nach dem Abkühlen wird das Reaktionsgemisch vorsichtig in eine Eis-Wasser-Mischung eingerührt. Der Niederschlag wird abgesaugt, in Wasser suspendiert und mit gesättigter Natriumkarbonatlösung neutralisiert. Nach dem Absaugen kristallisiert man aus Ethanol um.Ethyl chloro-e-methylthieno / aS-d / pyrimidine-e-ylcarboxylate, C 10 H 9 CIN 2 O 2 S (256.7) 0.015 mol of S-methyl-S 1 -dihydro-oxy-thieno ^ d-pyrimidine Ethyl 6-oxylcarboxylate, 9 ml of phosphorus oxychloride and 0.75 ml of Ν, Ν-dimethylaniline are refluxed for 14 hours. After cooling, the reaction mixture is carefully stirred into an ice-water mixture. The precipitate is filtered off with suction, suspended in water and neutralized with saturated sodium carbonate solution. After suction, crystallized from ethanol.

Schmelzpunkt: 115-117°C, Ausbeute: 75% Analog wird hergestellt:Melting point: 115-117 ° C, Yield: 75% Analog is prepared:

4-Chlor-2,5-dimetby!thieno/2,3-d/pyrimidin-6-ylcarbonsäureethylester,4-chloro-2,5-dimetby! Thieno / 2,3-d / pyrimidine-6-ylcarboxylate,

C11H11CIN2O2S, (270,7) Schmelzpunkt: 183-185,5°C, Ausbeute: 69%C 11 H 11 CIN 2 O 2 S, (270.7) Melting point: 183-185.5 ° C, yield: 69%

4-Chlor-5-methyl-2-phenylthieno/2,3-d/pyrimidin-6-ylcarbonsäureethylester,4-chloro-5-methyl-2-phenyl-thieno / 2,3-d / pyrimidine-6-ylcarboxylate,

C16H13CIN2O2S, (332,8) Schmelzpunkt: 149-152°C, Ausbeute: 86%C 16 H 13 CIN 2 O 2 S, (332.8) Melting point: 149-152 ° C, yield: 86%

Beispiel 2 4-Aminothieno/2,3-d/pyrimidin-6-ylcarbonsäureethylester,Example 2 4-aminothieno / 2,3-d / pyrimidin-6-ylcarboxylic acid ethyl ester,

0,005 mol 4-Chlorthieno/2,3-d/pyrimidin-6-ylcarbonsäureethylester werden mit 0,01 mol eines primären Amins in 18 ml Ethanol 4-8 Stunden unter Rückfluß erhitzt. Anschließend wird das Lösungsmittelvolumen im Vakuum auf 5 ml vermindert. Die beim Abkühlen ausfallenden Kristalle werden abgesaugt, mit Wasser gewaschen und aus dem angegebenen Lösungsmittel (Methanol = a. Ethanol = b, Essigsäureethylester = c) umkristallisiert0.005 mol of ethyl 4-chlorothieno / 2,3-d / pyrimidin-6-ylcarboxylate are refluxed with 0.01 mol of a primary amine in 18 ml of ethanol for 4-8 hours. Subsequently, the volume of solvent is reduced in vacuo to 5 ml. The crystals which precipitate on cooling are filtered off with suction, washed with water and recrystallised from the specified solvent (methanol = a. ethanol = b, ethyl acetate = c)

Nach dieser allgemeinen Vorschrift werden die in nachfolgender Tabelle zusammengefaßten Verbindungen hergestellt: According to this general rule, the compounds summarized in the following table are prepared:

Tabelle A-Aminothieno^S-d/pyrimidin-e-ylcarbonsäureethylester (gemäß Formel I mit R1 = ethyl, R2 = methyl)Table A-Aminothieno ^ Sd / pyrimidin-e-ylcarboxylic acid ethyl ester (according to formula I with R 1 = ethyl, R 2 = methyl)

R3 R4 Summenformel MolmasseR 3 R 4 Molar formula Molar mass

Schmelzpunktmelting point Ausbeuteyield (umkrist. aus)(umkrist. off) (%)(%) 165,5-167,5 (b)165.5-167.5 (b) 60.60th 166-169 (b)166-169 (b) 5555 158-160,5 (c)158-160.5 (c) 5858 138-140 (a)138-140 (a) 8282 154-155,5 (b)154-155.5 (b) 8585 159-162(b)159-162 (b) 8484 192-195 (b)192-195 (b) 5858 166-169 (b)166-169 (b) 7777 212,5-216 (b)212.5-216 (b) 4545 157,5-159,5 (b)157.5-159.5 (b) 7373 140-142(b)140-142 (b) 8989 179,5-182 (b)179.5-182 (b) 2525 143-145 (b)143-145 (b) 8282 149-154 (b)149-154 (b) 4141 117-119,5 (b)117-119.5 (b) 6464 75-80 ta)75-80 ta) 5555

HH CC eH5 eH 5 6Π4 O Cl6Π4 O Cl 6H4-p-F 6 H 4 -PF 8^178 ^ 17 C16H15N3O2SC 16 H 15 N 3 O 2 S 313,4313.4 HH CC 6H4~m — CH3 6 H4 ~ m - CH 3 6H4-m-CI 6 H 4 -m-Cl 6H4-p-OCH3 6 H 4 -p-OCH 3 C17H17N3O2SC 17 H 17 N 3 O 2 S 327,4327.4 HH CC 6H4-o-OCH3 6 H 4 -o-OCH3 C6H4-P-CIC 6 H 4 -P-CI 6H4-m-CI 6 H 4 -m-Cl C17H17N3O3SC 17 H 17 N 3 O 3 S 343,4343.4 HH CC 6H4-m-OCH3 6 H 4 -m-OCH 3 CC SH5 S H 5 C17H17N3O3SC 17 H 17 N 3 O 3 S 343,4343.4 HH C6H4-P-OCH3 C 6 H 4 -P-OCH 3 CC 6H„-m-OCH3 H 6 "-m-OCH 3 C17H17N3O3SC 17 H 17 N 3 O 3 S 343,4343.4 HH CC CC 6H4-m-CI 6 H 4 -m-Cl C16H14CIN3O2SC 16 H 14 CIN 3 O 2 S 347,8347.8 HH CC CC CH2-O-C4H3OCH 2 -OC 4 H 3 O C16H14CIN3O2SC 16 H 14 CIN 3 O 2 S 347,8347.8 HH CC CC C16H14CIN3O2SC 16 H 14 CIN 3 O 2 S 347,8347.8 HH CC C16H14FN3O2SC 16 H 14 FN 3 O 2 S 331,4331.4 CH3 CH 3 C13H19N3O3SC 13 H 19 N 3 O 3 S 357,4357.4 CH3 CH 3 C17H16CIN3O2SC 17 H 16 CIN 3 O 2 S 361,9361.9 C6H5 C 6 H 5 C22H19N3O2SC 22 H 19 N 3 O 2 S 389,5389.5 C6H6 C 6 H 6 C23H21N3O3SC 23 H 21 N 3 O 3 S 419,5419.5 C6H5 C 6 H 5 C22H18CIN3O2SC 22 H 18 CIN 3 O 2 S 423,9423.9 HH C15H15N3O3SC 15 H 15 N 3 O 3 S 317,4317.4 HH C18H27N3O2SC 18 H 27 N 3 O 2 S 349,5349.5

Formel IFormula I

Formel II Formel IIIFormula II Formula III

-1U-- 1 U

Formelblattformula sheet

MHRMHR

R1OOCR 1 OOC

E1, R2 E 1 , R 2

alkyl,alkyl,

H, alkyl, phenyl, alkyl, phenyl, subst· phenyl, aralkylH, alkyl, phenyl, alkyl, phenyl, substituted phenyl, aralkyl

R'R '

R1, R2 = alkyl,R 1 , R 2 = alkyl,

= H, alkyl, phenyl= H, alkyl, phenyl

ClCl

R1, R2 = alkyl,R 1 , R 2 = alkyl,

= H, alkyl, phenyl= H, alkyl, phenyl

Claims (1)

- 1 - Z4Ö Patentanspruch:- 1 - Z4Ö claim: Verfahren zur Herstellung von Thieno^^-d/pyrimidin-S-yl-carbonsäureestern der allgemeinen Formel I, worin R1, R2 = alkyl,A process for the preparation of thieno ^^ - d / pyrimidine-S-yl-carboxylic acid esters of general formula I, wherein R 1 , R 2 = alkyl, R3 = H, alkyl, phenyl,R 3 = H, alkyl, phenyl, R4 = alkyl, phenyl, subst. phenyl, aralkyl
bedeuten,R 4 = alkyl, phenyl, subst. phenyl, aralkyl
mean, gekennzeichnet dadurch, daß 3,4-Dihydro-4-oxothieno/2,3-d/-pyrimidin-6-ylcarbonsäureester der allgemeinen Formel II, worin R1, R2 und R3 obige Bedeutung besitzen, mit Phosphoroxidchlorid zu 4-Chlorthieno/2,3-d/pyrimidin-6-ylcarbonsäureestern der allgemeinen Formel III, worin R1, R2 und R3 obige Bedeutung besitzen, umgesetzt und anschließend diese 4-Chlorderivate mit primären Aminen zur Reaktion gebracht werden.characterized in that 3,4-dihydro-4-oxothieno / 2,3-d / -pyrimidin-6-ylcarboxylic esters of the general formula II wherein R 1 , R 2 and R 3 have the above meaning, with phosphorus oxychloride to 4-Chlororthieno / 2,3-d / pyrimidin-6-ylcarboxylic esters of general formula III, wherein R 1 , R 2 and R 3 have the above meaning, reacted and then these 4-chloro derivatives are reacted with primary amines.
DD27250685A 1985-01-11 1985-01-11 PROCESS FOR PREPARING 4-BASED SUBSTITUTED THIENO / 2,3-D / PYRIMIDIN-6-YLCARBOXYANESEESTERS DD248593A1 (en)

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Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004087056A3 (en) * 2003-03-28 2005-02-24 Scios Inc BI-CYCLIC PYRIMIDINE INHIBITORS OF TGFβ
AU2004247470B2 (en) * 2003-06-11 2009-04-23 Xention Limited Thienopyrimidine derivatives as potassium channel inhibitors
US7576212B2 (en) 2004-12-09 2009-08-18 Xention Limited Thieno[2,3-B] pyridines as potassium channel inhibitors
WO2010023181A1 (en) * 2008-08-26 2010-03-04 Boehringer Ingelheim International Gmbh Thienopyrimidines for pharmaceutical compositions
US8022076B2 (en) 2003-06-11 2011-09-20 Xention Limited Substituted thieno[2,3-d]pyrimidines as potassium channel inhibitors
CN102858782A (en) * 2010-02-26 2013-01-02 贝林格尔.英格海姆国际有限公司 4 - [cycloalkyloxy (hetero) arylamino] thieno [2, 3 - d] pyrimidines having mnkl/ mnk2 inhibiting activity for pharmaceutical compositions
US8633201B2 (en) 2006-04-07 2014-01-21 Boehringer Ingelheim International Gmbh Thienopyrimidines having Mnk1/Mnk2 inhibiting activity for pharmaceutical compositions
US8648068B2 (en) 2010-02-26 2014-02-11 Boehringer Ingelheim International Gmbh Heterocycloalkyl-containing thienopyrimidines for pharmaceutical compositions
US8697713B2 (en) 2006-07-10 2014-04-15 Boehringer Ingelheim International Gmbh Pyrrolopyrimidines for pharmaceutical compositions
US8853193B2 (en) 2010-02-26 2014-10-07 Boehringer Ingelheim International Gmbh Thienopyrimidines containing a substituted alkyl group for pharmaceutical compositions
US9216992B2 (en) 2005-12-09 2015-12-22 Xention Limited Thieno[3,2-c]pyridine potassium channel inhibitors
EP3116882A4 (en) * 2014-03-11 2017-08-02 Godavari Biorefineries Ltd. Compounds for eradicating or inhibiting proliferation of cancer stem cells

Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004087056A3 (en) * 2003-03-28 2005-02-24 Scios Inc BI-CYCLIC PYRIMIDINE INHIBITORS OF TGFβ
AU2004247470B2 (en) * 2003-06-11 2009-04-23 Xention Limited Thienopyrimidine derivatives as potassium channel inhibitors
US8022076B2 (en) 2003-06-11 2011-09-20 Xention Limited Substituted thieno[2,3-d]pyrimidines as potassium channel inhibitors
US7576212B2 (en) 2004-12-09 2009-08-18 Xention Limited Thieno[2,3-B] pyridines as potassium channel inhibitors
US8193215B2 (en) 2004-12-09 2012-06-05 Xention Limited Thieno[2 3-b]pyridines as potassium channel inhibitors
US9216992B2 (en) 2005-12-09 2015-12-22 Xention Limited Thieno[3,2-c]pyridine potassium channel inhibitors
US8633201B2 (en) 2006-04-07 2014-01-21 Boehringer Ingelheim International Gmbh Thienopyrimidines having Mnk1/Mnk2 inhibiting activity for pharmaceutical compositions
US8697713B2 (en) 2006-07-10 2014-04-15 Boehringer Ingelheim International Gmbh Pyrrolopyrimidines for pharmaceutical compositions
US8486953B2 (en) 2008-08-26 2013-07-16 Boehringer Ingelheim International Gmbh Thienopyrimidines for pharmaceutical compositions
JP2012500825A (en) * 2008-08-26 2012-01-12 ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング Thienopyrimidine for pharmaceutical composition
WO2010023181A1 (en) * 2008-08-26 2010-03-04 Boehringer Ingelheim International Gmbh Thienopyrimidines for pharmaceutical compositions
CN102858782A (en) * 2010-02-26 2013-01-02 贝林格尔.英格海姆国际有限公司 4 - [cycloalkyloxy (hetero) arylamino] thieno [2, 3 - d] pyrimidines having mnkl/ mnk2 inhibiting activity for pharmaceutical compositions
US8648068B2 (en) 2010-02-26 2014-02-11 Boehringer Ingelheim International Gmbh Heterocycloalkyl-containing thienopyrimidines for pharmaceutical compositions
US8754079B2 (en) 2010-02-26 2014-06-17 Boehringer Ingelheim International Gmbh Cycloalkyl containing thienopyrimidines for pharmaceutical compositions
US8853193B2 (en) 2010-02-26 2014-10-07 Boehringer Ingelheim International Gmbh Thienopyrimidines containing a substituted alkyl group for pharmaceutical compositions
EP3116882A4 (en) * 2014-03-11 2017-08-02 Godavari Biorefineries Ltd. Compounds for eradicating or inhibiting proliferation of cancer stem cells

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