DD285356A5 - PROCESS FOR PREPARING 4-HYDROXY-6-OXO-6,7-DIHYDROTHIENO [2,3-B] PYRIDINE-5-CARBONITRILENE - Google Patents
PROCESS FOR PREPARING 4-HYDROXY-6-OXO-6,7-DIHYDROTHIENO [2,3-B] PYRIDINE-5-CARBONITRILENE Download PDFInfo
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- DD285356A5 DD285356A5 DD32965689A DD32965689A DD285356A5 DD 285356 A5 DD285356 A5 DD 285356A5 DD 32965689 A DD32965689 A DD 32965689A DD 32965689 A DD32965689 A DD 32965689A DD 285356 A5 DD285356 A5 DD 285356A5
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- DD
- German Democratic Republic
- Prior art keywords
- oxo
- hydroxy
- dihydro
- pyridine
- thieno
- Prior art date
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- 238000004519 manufacturing process Methods 0.000 title 1
- -1 cyanoacetic acid ester Chemical class 0.000 claims abstract description 14
- 238000000034 method Methods 0.000 claims abstract description 14
- OHMLBZKIUZTEOC-UHFFFAOYSA-N 2-aminothiophene-3-carboxylic acid Chemical class NC=1SC=CC=1C(O)=O OHMLBZKIUZTEOC-UHFFFAOYSA-N 0.000 claims abstract description 4
- MLIREBYILWEBDM-UHFFFAOYSA-N anhydrous cyanoacetic acid Natural products OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims abstract 5
- 238000002360 preparation method Methods 0.000 claims abstract 4
- 239000003814 drug Substances 0.000 claims abstract 2
- 239000000543 intermediate Substances 0.000 claims abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N butadiene group Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 claims 2
- ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 claims 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 2
- CRRUFISVDCIBAP-UHFFFAOYSA-N 4-hydroxy-2-oxo-1h-quinoline-3-carbonitrile Chemical compound C1=CC=C2C(=O)C(C#N)=C(O)NC2=C1 CRRUFISVDCIBAP-UHFFFAOYSA-N 0.000 claims 1
- WZKFAAIOEBUBFO-UHFFFAOYSA-N 4-hydroxy-7h-thieno[2,3-b]pyridin-6-one Chemical class OC1=CC(=O)NC2=C1C=CS2 WZKFAAIOEBUBFO-UHFFFAOYSA-N 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 claims 1
- 125000005605 benzo group Chemical group 0.000 claims 1
- VYFOAVADNIHPTR-UHFFFAOYSA-N isatoic anhydride Chemical compound NC1=CC=CC=C1CO VYFOAVADNIHPTR-UHFFFAOYSA-N 0.000 claims 1
- 150000002825 nitriles Chemical group 0.000 claims 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims 1
- 238000001149 thermolysis Methods 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 abstract description 4
- 239000011734 sodium Substances 0.000 abstract description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract description 3
- 230000001476 alcoholic effect Effects 0.000 abstract 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
- 238000001953 recrystallisation Methods 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical compound N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 description 1
- KYRNAMLXNBXIPW-UHFFFAOYSA-N 4-hydroxy-6-oxo-3-phenyl-7h-thieno[2,3-b]pyridine-5-carbonitrile Chemical compound C1=2C(=O)C(C#N)=C(O)NC=2SC=C1C1=CC=CC=C1 KYRNAMLXNBXIPW-UHFFFAOYSA-N 0.000 description 1
- AFAZWNIYLKTJSO-UHFFFAOYSA-N C(C)OC(=O)C=1C(=C(SC1N)C(=O)O)C Chemical compound C(C)OC(=O)C=1C(=C(SC1N)C(=O)O)C AFAZWNIYLKTJSO-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- JYSDXODDWAQWJR-UHFFFAOYSA-N ethyl 2-amino-4,5-dimethylthiophene-3-carboxylate Chemical compound CCOC(=O)C1=C(N)SC(C)=C1C JYSDXODDWAQWJR-UHFFFAOYSA-N 0.000 description 1
- WYTHTMKMOSPACP-UHFFFAOYSA-N ethyl 2-amino-4-phenylthiophene-3-carboxylate Chemical compound CCOC(=O)C1=C(N)SC=C1C1=CC=CC=C1 WYTHTMKMOSPACP-UHFFFAOYSA-N 0.000 description 1
- MKJQYFVTEPGXIE-UHFFFAOYSA-N ethyl 2-aminothiophene-3-carboxylate Chemical compound CCOC(=O)C=1C=CSC=1N MKJQYFVTEPGXIE-UHFFFAOYSA-N 0.000 description 1
- OYSLMAQEMAJMCL-UHFFFAOYSA-N ethyl thiophene-3-carboxylate Chemical compound CCOC(=O)C=1C=CSC=1 OYSLMAQEMAJMCL-UHFFFAOYSA-N 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- PLLLBSPBFALBFB-UHFFFAOYSA-N methyl 2-amino-4-methylthiophene-3-carboxylate Chemical compound COC(=O)C=1C(C)=CSC=1N PLLLBSPBFALBFB-UHFFFAOYSA-N 0.000 description 1
- GHPDMFBHITXJAZ-UHFFFAOYSA-N methyl 2-amino-5-methylthiophene-3-carboxylate Chemical compound COC(=O)C=1C=C(C)SC=1N GHPDMFBHITXJAZ-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Landscapes
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
Die Erfindung betrifft ein Verfahren zur Herstellung von * die als Zwischenprodukte fuer Pharmazeutika Verwendung finden koennen. Erfindungsgemaesz werden diese Verbindungen durch ein einfaches Verfahren zugaenglich gemacht, indem 2-Amino-thiophen-3-carbonsaeureester mit Cyanessigsaeureester in alkoholischer Loesung und in Gegenwart von Natriumalkoholat umgesetzt werden.{* 2-Amino-thiophen-3-carbonsaeureester; Cyanessigsaeureester; Natriumalkoholat}The invention relates to a process for the preparation of * which can be used as intermediates for pharmaceuticals use. According to the invention, these compounds are made accessible by a simple process by reacting 2-amino-thiophene-3-carboxylic acid esters with cyanoacetic acid ester in alcoholic solution and in the presence of sodium alcoholate. {* 2-Amino-thiophene-3-carboxylic acid ester; cyanoacetic; sodium alcoholate}
Description
Aufgabe der Erfindung ist es, 4-Hydroxy-6-oxo-6,7-dihydro-thieno[2,3-b]pyridin-5-carbonitrile durch ein einfaches und neues Verfahren herzustellen.The object of the invention is to produce 4-hydroxy-6-oxo-6,7-dihydro-thieno [2,3-b] pyridine-5-carbonitriles by a simple and novel process.
Ef iindungsgemäß wird die Aufgabe dadurch gelöst, daß 4-Hydroxy-6-oxo-6,7-dihydro-thieno[2,3-b]pyridin-5-carbonitrile der allgemeinen Formel I,According to the invention, the object is achieved by reacting 4-hydroxy-6-oxo-6,7-dihydro-thieno [2,3-b] pyridine-5-carbonitriles of the general formula I
worin R1 und R2 jeweils ein Wasserstoffatom, eine Alkyl- oder Arylgruppe, zusammen eine überbrückende Tri-, Tetra-, Pantamethylen- oder Butadiengruppierung bedeuten und R2 außerdem eine Acyl-, Alkoxycarbonyl-, Carbamoyl- oder Acetylaminogruppe sein kann, hergestellt werden, indem 2-Amino-thiophen-3-carbonsäureester der Formel II,wherein R 1 and R 2 each represent a hydrogen atom, an alkyl or aryl group, together represent a bridging tri-, tetra-, pantamethylene or butadiene moiety, and R 2 may also be an acyl, alkoxycarbonyl, carbamoyl or acetylamino group in that 2-amino-thiophene-3-carboxylic esters of the formula II,
rV .XO2R3 rV .XO 2 R 3
in der R' und R2 die oben angegebene Bedeutung besitzen und R3 eine Alkylgruppe darstellt, mit Cyanessigsäureester der Formel III,in which R 'and R 2 have the abovementioned meaning and R 3 represents an alkyl group, with cyanoacetic acid ester of the formula III,
worin R eine Alkylgruppe bedeutet, umgesetzt werden. Dies geschieht in einem Lösungsmittel vorzugsweise Alkohol und in Gegenwart einer Base, vorzugsweise Natriumalkoholat, die als Cyclisierungsmittel dient und durch Salzbildung verbracht wird. Die benötigten Ausgangsverbindungen Il sind leicht nach Chem. Ber. 99 (1966) 94 und Heterocyclic Compounds, Vol. 44, Part 2, Wiley and Sons, New York 1986, herstellbar.wherein R represents an alkyl group, are reacted. This is done in a solvent, preferably alcohol and in the presence of a base, preferably sodium alkoxide, which serves as a cyclizing agent and is brought by salt formation. The required starting compounds II are easily according to Chem. Ber. 99 (1966) 94 and Heterocyclic Compounds, Vol. 44, Part 2, Wiley and Sons, New York 1986.
4-Hydroxy-3-methyl-6-oxo-6,7-dihydro-thieno[2,3-blpyridin-5-carbonitril4-hydroxy-3-methyl-6-oxo-6,7-dihydro-thieno [2,3-blpyridin-5-carbonitrile
30mrnol Cyanessigsäureethyiester versetzt und unter Rühren und Feuchtigkeitsausschluß 1 Std. zum Sieden erhitzt. Nach dem30mnol Cyanessigsäureethyiester added and heated with stirring and exclusion of moisture for 1 h. Boil. After this
4-Hydroxy-2-methyl-6-oxo-6,7-dihydro-thieno[2,3-b]pyridin-5-carbonitril4-hydroxy-2-methyl-6-oxo-6,7-dihydro-thieno [2,3-b] pyridine-5-carbonitrile
umgesetzt und aufgearbeitet. Ausbeute 73%, F.340-3450C, Zers., nach Umkristallisieren aus Dimethylformamid/Wasser.implemented and worked up. Yield 73%, F.340-345 0 C, dec., After recrystallisation from dimethylformamide / water.
4-Hydroxy-2,3-dimethyl-6-oxo-6,7-dihydro-thieno[2,3-b]pyridin-5-carbonitril4-Hydroxy-2,3-dimethyl-6-oxo-6,7-dihydro-thieno [2,3-b] pyridine-5-carbonitrile
umgesetzt. Ausbeute 85%, F.224-227°C nach Umkristallisieren aus Dimethylformamid.implemented. Yield 85%, F.224-227 ° C after recrystallization from dimethylformamide.
4-Hydroxy-2,3-tetramethylen-6-oxo-6,7-dihydro-thieno[2,3-b]pyridin-5-carbonitril4-Hydroxy-2,3-tetramethylene-6-oxo-6,7-dihydro-thieno [2,3-b] pyridine-5-carbonitrile
umgesetzt und aufgearbeitet. Ausbeute 92%, F.315-318°C nach Umkristallisieren aus Dimethylformamid.implemented and worked up. Yield 92%, F.315-318 ° C after recrystallization from dimethylformamide.
4-Hydroxy-6-oxo-3-phenyl-6,7-dihydro-thieno[2,3-b]pyridin-5-carbonitril4-hydroxy-6-oxo-3-phenyl-6,7-dihydro-thieno [2,3-b] pyridine-5-carbonitrile
4-Hydroxy-3-methyl-6-oxo-2-phenyl-e,7-dihydro-thieno[2,3-b]pyridin-5-carbonitril Nach der für Beispiel 1 angegebenen Vorschrift werden 10 mmol 2-Amlno-4-methyl-5-phenyl-thiophdn-3-carbonsäureethvlesiar umgesetzt und aufgearbeitet. Ausbeute 89%, F.335-340°C aus Dimethylformamid.4-Hydroxy-3-methyl-6-oxo-2-phenyl-e, 7-dihydro-thieno [2,3-b] pyridine-5-carbonitrile Following the procedure given for Example 1, 10 mmol of 2-Amlno-4 Methyl-5-phenyl-thiophdn-3-carbonsäureethvlesiar reacted and worked up. Yield 89%, F.335-340 ° C from dimethylformamide.
4-Hydrüxy-2-methyl-6-oxo-3-phenyl-6,7-dihydro-thienoI2,3-b]pyridin-5-carbonitril Entsprechend der für Beispiel 1 angegebenen Vorschrift werden lOmmol 2-Amino-5-methyl-4-phenyl-thiophen-3-carbonsäureethylester umgesetzt und aufgearbeitet. Ausbeute 79%, F. 260-2630C nach Umkristallisieren aus Eisessig.4-hydroxy-2-methyl-6-oxo-3-phenyl-6,7-dihydro-thienoI2,3-b] pyridine-5-carbonitrile In accordance with the instructions given for Example 1, 10 mmol of 2-amino-5-methyltrichloro 4-phenyl-thiophene-3-carboxylic acid ethyl ester reacted and worked up. Yield 79%, mp 260-263 0 C after recrystallization from glacial acetic acid.
5-Cyan-4-hydroxy-3-methyl-6-oxo-6,7-dihydro-thieno[2,3-b]pyridin-2-carbonsäureethylester Analog der für Beispiel 1 angegebenen Vorschrift v/erden lOmmol 2-Amino-4-methyl-thiophen-3,5-biscarbonsäureethylester umgesetzt und aufgearbeitet. Ausbeute 75%, F.223-226°C nach Umkriflallisieren aus Dimethylformamid.Ethyl 5-cyano-4-hydroxy-3-methyl-6-oxo-6,7-dihydro-thieno [2,3-b] pyridine-2-carboxylate Analogously to the procedure given for Example 1, 10 mmol of 2-amino 4-methyl-thiophene-3,5-biscarboxylic acid ethyl ester reacted and worked up. Yield 75%, F.223-226 ° C after recrystallization from dimethylformamide.
2-Acetyl-4-hydroxy-3-methyl-6-oxo-6,7-dihydro-thieno[2,3-b]pyridin-5-carbonitril Wie für Beispiel 1 beschrieben wurde, werden lOmmol B-Acetyl^-Amino^-methyl-thiophen-S-carbonsäureethylester umgesetzt und aufgearbeitet. Ausbeute 61 %, F.350-3530C nach Umkristallisieren aus Dimethylformamid.2-Acetyl-4-hydroxy-3-methyl-6-oxo-6,7-dihydro-thieno [2,3-b] pyridine-5-carbonitrile As described for Example 1, 10 mmol of B-acetyl-amino reacted and worked up ethyl-methyl-thiophene-S-carboxylate. Yield 61%, F.350-353 0 C after recrystallization from dimethylformamide.
2-Acetylamino-4-hydroxy-3-methyl-6-oxo-6,7-dihydro-thieno(2,3-b]pyridin-5-carbonitril Nach der für Beispiel 1 angegebenen Vorschrift werden lOmmol 5-Acetyl-amino-2-amino-4-methyl-thiophen-3-carbonsäureethylester umgesetzt und aufgearbeitet. Ausbeute 42%, F. > 360°C nach Umkristallisieren aus Pyridin.2-Acetylamino-4-hydroxy-3-methyl-6-oxo-6,7-dihydro-thieno (2,3-b] pyridine-5-carbonitrile Following the procedure given for Example 1, 10 mmol of 5-acetylamino 2-amino-4-methyl-thiophene-3-carboxylic acid ethyl ester and worked up Yield 42%, mp> 360 ° C. after recrystallization from pyridine.
4-Hydroxy-2-oxo-1,2-dihydro-(1]benzo-thieno[2,3-b]pyridin-3-carbonitril Wie in der für Beispiel 1 ausgegebenen Vorschrift werden lOmmol 2-Amino-bonzo[b]thiophen-3-carbonsäureethylester umgesetzt und aufgearbeitet. Ausbeute 43%, F.350-353°C nach Umkristallisieren aus Dimethylformamid.4-Hydroxy-2-oxo-1,2-dihydro- (1) benzothieno [2,3-b] pyridine-3-carbonitrile As in the procedure given for Example 1, 10 mmol of 2-amino-benzo [b] reacted and worked up with ethyl thiophene-3-carboxylate, yield 43%, mp 350-353 ° C. after recrystallization from dimethylformamide.
4-Hydroxy-6-oxo-6,7-dihydro-thieno[2,3-b]pyridin-5-carbonitril Wie für Beispiel 1 beschrieben, werden lOmmol 2-Amino-thiophen-3-carbonsäureethylester umgesetzt. Nach dam Erkalten wird der Alkohol weitgehend abdestilliert, der Rückstand mit 100ml Wasser verdünnt, filtriert, angesäuert und abgesaugt.4-Hydroxy-6-oxo-6,7-dihydro-thieno [2,3-b] pyridine-5-carbonitrile As described for Example 1, 10 mmol of ethyl 2-amino-thiophene-3-carboxylate are reacted. After dam cooling, the alcohol is largely distilled off, the residue diluted with 100 ml of water, filtered, acidified and filtered with suction.
Ausbeute 51 %, F.322-325°C, Zers., nach Umkristallisieren aus Ethanol.Yield 51%, F.322-325 ° C, dec., After recrystallization from ethanol.
Claims (5)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DD32965689A DD285356A5 (en) | 1989-06-16 | 1989-06-16 | PROCESS FOR PREPARING 4-HYDROXY-6-OXO-6,7-DIHYDROTHIENO [2,3-B] PYRIDINE-5-CARBONITRILENE |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DD32965689A DD285356A5 (en) | 1989-06-16 | 1989-06-16 | PROCESS FOR PREPARING 4-HYDROXY-6-OXO-6,7-DIHYDROTHIENO [2,3-B] PYRIDINE-5-CARBONITRILENE |
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| Publication Number | Publication Date |
|---|---|
| DD285356A5 true DD285356A5 (en) | 1990-12-12 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD32965689A DD285356A5 (en) | 1989-06-16 | 1989-06-16 | PROCESS FOR PREPARING 4-HYDROXY-6-OXO-6,7-DIHYDROTHIENO [2,3-B] PYRIDINE-5-CARBONITRILENE |
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| Country | Link |
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| DD (1) | DD285356A5 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005042540A1 (en) * | 2003-10-24 | 2005-05-12 | Celltech R & D Limited | Thieno-pyridinone derivatives as kinase inhibitors |
-
1989
- 1989-06-16 DD DD32965689A patent/DD285356A5/en not_active IP Right Cessation
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005042540A1 (en) * | 2003-10-24 | 2005-05-12 | Celltech R & D Limited | Thieno-pyridinone derivatives as kinase inhibitors |
| US7795256B2 (en) | 2003-10-24 | 2010-09-14 | Ucb Pharma S.A. | Thieno-pyridinone derivatives as kinase inhibitors |
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