DE10042093A1 - Anticonvulsant 6,7-dihydro-pyrrolo [3,4-d] pyridin-5-ones and process for their preparation - Google Patents
Anticonvulsant 6,7-dihydro-pyrrolo [3,4-d] pyridin-5-ones and process for their preparationInfo
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- DE10042093A1 DE10042093A1 DE10042093A DE10042093A DE10042093A1 DE 10042093 A1 DE10042093 A1 DE 10042093A1 DE 10042093 A DE10042093 A DE 10042093A DE 10042093 A DE10042093 A DE 10042093A DE 10042093 A1 DE10042093 A1 DE 10042093A1
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
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- A61P25/00—Drugs for disorders of the nervous system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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Abstract
Description
Die Erfindung betrifft 6,7-Dihydro-pyrrolo[3,4-b]pyridin-5-one, die in 6-Stellung einen Aralkyl-Rest enthalten, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel, insbesondere zur Behandlung von Epilepsien verschiedener Formen.The invention relates to 6,7-dihydro-pyrrolo [3,4-b] pyridin-5-ones in the 6-position contain an aralkyl radical, process for their preparation and their use as a drug, especially for the treatment of various epilepsy To form.
Bisher wurde die Synthese von einem 6,7-Dihydro-pyrrolo[3,4-b]pyridin-5-on beschrieben, das in 6-Stellung den Aralkyl-Rest Benzyl enthält [Sato, Y.; Iwashige, T.; Miyadera, T., Chem. Pharm. Bull. 1960, 8, 427-35]. 6-Benzyl-6,7- dihydro-5H-pyrrolo[3,4-b]pyridin-5-on wird erhalten, indem Furo[3,4-b]pyridin- 5(7H)-on mit 2 Äquivalenten Benzylamin bei hohen Temperaturen (200°C) erhitzt wird. Die Verbindung wurde auf hypotensive Aktivität geprüft. Eine antikonvulsive Wirkung wird nicht erwähnt oder nahegelegt.So far, the synthesis of a 6,7-dihydro-pyrrolo [3,4-b] pyridin-5-one which contains the aralkyl radical benzyl in the 6-position [Sato, Y .; Iwashige, T .; Miyadera, T., Chem. Pharm. Bull. 1960, 8, 427-35]. 6-benzyl-6,7- dihydro-5H-pyrrolo [3,4-b] pyridin-5-one is obtained by furo [3,4-b] pyridin- 5 (7H) -one heated with 2 equivalents of benzylamine at high temperatures (200 ° C) becomes. The connection was checked for hypotensive activity. An anticonvulsant Effect is not mentioned or suggested.
6-(2-Phenylethyl)- oder 6-(1-Phenylethyl)-substituierte 6,7-Dihydro-pyrrolo[3,4- b]pyridin-5-one sind nach einem Verfahren von B. Gutkowska zugänglich [Gutkowska, B.; Kabzinska, Z.; Wasiak, J., Acta Pol. Pharm. 1987, 44(2), 242-4]. Für die Herstellung größerer Mengen ist das Verfahren unvorteilhaft, da die entsprechenden Pyridindicarboxamide mit Zinn zu den gewünschten Endprodukten reduziert werden. Die biologische Wirkung dieser Verbindungen wurde nicht untersucht.6- (2-phenylethyl) - or 6- (1-phenylethyl) substituted 6,7-dihydropyrrolo [3,4- b] pyridin-5-ones are accessible by a method from B. Gutkowska [Gutkowska, B .; Kabzinska, Z .; Wasiak, J., Acta Pol. Pharm. 1987, 44 (2), 242-4]. The process is disadvantageous for the production of larger quantities, since the appropriate pyridinedicarboxamides with tin to the desired End products are reduced. The biological effects of these compounds has not been examined.
Bekannte Antikonvulsiva haben zum einen den Nachteil, dass unerwünschte Nebenwirkungen, wie Neurotoxizität und Idiosynkrasien, auftreten und zum anderen diese bei bestimmten Formen der Epilepsie nicht wirksam sind.Known anticonvulsants have the disadvantage that they are undesirable Side effects such as neurotoxicity and idiosyncrasies occur and lead to others these are not effective for certain forms of epilepsy.
Der Erfindung liegt deshalb die Aufgabe zugrunde, nach einem leicht handhabbaren Verfahren Verbindungen mit günstigen pharmakologischen Eigenschaften zur Verfügung zu stellen, die antikonvulsiv wirken und als Arzneimittel, insbesondere zur Behandlung von Epilepsien, einsetzbar sind.The invention is therefore based on the object, according to an easy manageable process compounds with favorable pharmacological To provide properties that act as an anticonvulsant and as Medicines, especially for the treatment of epilepsy, can be used.
Entsprechend der vorliegenden Erfindung sind diese neuen Verbindungen 6,7-
Dihydro-5H-pyrrolo[3,4-b]pyridin-5-one der allgemeinen Formel 1
According to the present invention, these new compounds are 6,7-dihydro-5H-pyrrolo [3,4-b] pyridin-5-ones of the general formula 1
worin
R1 = (C1-C4)alkyl, (C1-C2)alkoxy, Trifluormethyl oder Halogen und
n = 1-3 ist.wherein
R 1 = (C 1 -C 4 ) alkyl, (C 1 -C 2 ) alkoxy, trifluoromethyl or halogen and
n = 1-3.
Als Beispiele für Verbindungen der allgemeinen Formel 1 seien genannt:
6-(4-Methylbenzyl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-on
6-(4-Methoxybenzyl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-on
6-(4-Chlorbenzyl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-on
6-(3-Chlorbenzyl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-on
6-(2-Chlorbenzyl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-on
6-(4-Fluorbenzyl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-on
6-(2-Fluorbenzyl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-on
6-(2,6-Difluorbenzyl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-on
6-(2-Trifluormethylbenzyl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-on
Examples of compounds of general formula 1 are:
6- (4-methylbenzyl) -6,7-dihydro-5H-pyrrolo [3,4-b] pyridin-5-one
6- (4-methoxybenzyl) -6,7-dihydro-5H-pyrrolo [3,4-b] pyridin-5-one
6- (4-chlorobenzyl) -6,7-dihydro-5H-pyrrolo [3,4-b] pyridin-5-one
6- (3-chlorobenzyl) -6,7-dihydro-5H-pyrrolo [3,4-b] pyridin-5-one
6- (2-chlorobenzyl) -6,7-dihydro-5H-pyrrolo [3,4-b] pyridin-5-one
6- (4-fluorobenzyl) -6,7-dihydro-5H-pyrrolo [3,4-b] pyridin-5-one
6- (2-fluorobenzyl) -6,7-dihydro-5H-pyrrolo [3,4-b] pyridin-5-one
6- (2,6-difluorobenzyl) -6,7-dihydro-5H-pyrrolo [3,4-b] pyridin-5-one
6- (2-trifluoromethylbenzyl) -6,7-dihydro-5H-pyrrolo [3,4-b] pyridin-5-one
Das Verfahren zur Herstellung von Verbindungen der Formel 1 geht vom bekannten Furo[3,4-b]pyridin-5(7H)-on (Formel 5) aus [Inoue, K. et al., Synthesis 1997, 113-116)]. Die Verbindung der Formel 5 wird in drei Stufen zu Verbindungen der allgemeinen Formel 1 umgesetzt.The process for the preparation of compounds of formula 1 starts from known furo [3,4-b] pyridin-5 (7H) -one (formula 5) from [Inoue, K. et al., Synthesis 1997, 113-116)]. The compound of formula 5 becomes compounds in three stages the general formula 1 implemented.
Durch Erhitzen der Verbindung der Formel 5 mit substituierten Benzylaminen der
allgemeinen Formel 4 in vorzugsweise höher siedenden Alkoholen werden
benzylsubstituierte 2-Hydroxymethyl-nicotinsäureamide der allgemeinen Formel 3
erhalten. Diese 2-Hydroxymethyl-nicotinsäureamide werden mit SOCl2 zu den 2-
Chlormethyl-nicotinsäureamiden der allgemeinen Formel 2 umgesetzt. In
Gegenwart eines Lösungsmittels, das eine HCl-affine Komponente, vorzugsweise
K2CO3, enthält, erfolgt der Ringschluß zu Verbindungen der allgemeinen Formel 1.
Heating the compound of the formula 5 with substituted benzylamines of the general formula 4 in preferably higher-boiling alcohols gives benzyl-substituted 2-hydroxymethyl-nicotinamide of the general formula 3. These 2-hydroxymethyl-nicotinamides are reacted with SOCl 2 to give the 2-chloromethyl-nicotinamides of the general formula 2. In the presence of a solvent which contains an HCl-affine component, preferably K 2 CO 3 , the ring is closed to give compounds of the general formula 1.
Die erfindungsgemäßen Verbindungen oder deren pharmazeutisch verwendbaren Salze sind zur Herstellung pharmazeutischer Zusammensetzungen geeignet. Die pharmazeutischen Zusammensetzungen beziehungsweise Medikamente können eine oder mehrere der erfindungsgemäßen Verbindungen enthalten. Zur Herstellung der pharmazeutischen Zubereitungen können die üblichen pharmazeutischen Träger- und Hilfsstoffe verwendet werden. Die Arzneimittel können beispielsweise parenteral (z. B. intravenös, intramuskulär, subkutan) oder oral verabreicht werden.The compounds of the invention or their pharmaceutically usable Salts are suitable for the manufacture of pharmaceutical compositions. The pharmaceutical compositions or drugs contain one or more of the compounds according to the invention. to Production of the pharmaceutical preparations can be the usual pharmaceutical carriers and excipients are used. The medicines can for example be parenteral (e.g. intravenous, intramuscular, subcutaneous) or administered orally.
Die Applikationsformen können nach in der pharmazeutischen Praxis allgemein bekannten und üblichen Verfahren hergestellt werden.The application forms can be used in general in pharmaceutical practice known and customary processes can be produced.
Die erfindungsgemäßen Verbindungen weisen starke antikonvulsive Wirkungen auf, ebenso die bereits beschriebenen Verbindungen 6-Benzyl-6,7-dihydro pyrrolo[3,4-b]pyridin-5-on, 6-(1-Phenylethyl)-6,7-dihydro-pyrrolo[3,4-b]pyridin-5-on als Razemat oder deren Enantiomere sowie 6-(2-Phenylethyl)-6,7-dihydro pyrrolo[3,4-b]pyridin-5-on. The compounds according to the invention have strong anticonvulsant effects on, as well as the compounds 6-benzyl-6,7-dihydro already described pyrrolo [3,4-b] pyridin-5-one, 6- (1-phenylethyl) -6,7-dihydro-pyrrolo [3,4-b] pyridin-5-one as a racemate or its enantiomers and 6- (2-phenylethyl) -6,7-dihydro pyrrolo [3,4-b] pyridin-5-one.
Die erfindungsgemäßen Verbindungen wurden in vivo nach i.p.-Applikation an Mäusen nach dem international üblichen Standard (Pharmac. Weekblad, Sc. Ed. 14, 132 (1992) und Antiepileptic Drugs, Third. Ed., Raven Press, New York 1989) auf ihre antikonvulsive Wirkung getestet (Tab. 1).The compounds according to the invention were applied in vivo after i.p. application Mice according to the international standard (Pharmac. Weekblad, Sc. Ed. 14, 132 (1992) and Antiepileptic Drugs, Third. Ed., Raven Press, New York 1989) tested for its anticonvulsant effect (Tab. 1).
Beispielsweise wurde für die neue Verbindung 8, 6-(2,6-Difluorbenzyl)-6,7- dihydro-5H-pyrrolo[3,4-b]pyridin-5-on, bei der Ratte im Maximalen Elektroschock die ED50 (p. o.) zu 5,0 mg/kg bestimmt. Diese Verbindung ist auch wirksam in Kindlingmodellen (Hippocampales Kindling, ED50 = 28,8 mg/kg). Hervorzuheben ist die bis 500 mg/kg am Rotarod nicht nachzuweisende Neurotoxizität. Die Substanz verursacht bei der Ratte (p. o.) keine Toleranz - ein wichtiges Kriterium für den therapeutischen Wert eines Antiepileptikums.For example, for the new compound 8, 6- (2,6-difluorobenzyl) -6,7-dihydro-5H-pyrrolo [3,4-b] pyridin-5-one, the ED 50 ( po) determined to be 5.0 mg / kg. This compound is also effective in kindling models (Hippocampal Kindling, ED 50 = 28.8 mg / kg). The neurotoxicity that cannot be demonstrated up to 500 mg / kg on the Rotarod should be emphasized. The substance does not cause tolerance in the rat (po) - an important criterion for the therapeutic value of an anti-epileptic.
Die folgenden Beispiele dienen der weiteren Erläuterung der Erfindung ohne diese zu beschränken.The following examples serve to further illustrate the invention without it to restrict.
Zu 0,1 mol Furopyridin-5-on (Formel 5) in 60 ml n-Butanol werden (0,11 mol) Benzylamin (allgemeine Formel 4) und 0,1 g Toluolsulfonsäure gegeben. Die Mischung wird 6 h unter Rückfluss erhitzt. Anschließend wird unter Rühren abgekühlt, der Niederschlag abgesaugt und mit Ethanol gewaschen. Das Produkt, 2-Hydroxymethyl-nicotinsäureamid (allgemeine Formel 3), wird ohne Umkristallisation in der 2. Stufe eingesetzt.To 0.1 mol of furopyridin-5-one (formula 5) in 60 ml of n-butanol (0.11 mol) Benzylamine (general formula 4) and 0.1 g of toluenesulfonic acid. The Mixture is heated under reflux for 6 h. Then stirring cooled, the precipitate filtered off and washed with ethanol. The product, 2-hydroxymethyl nicotinamide (general formula 3), is without Recrystallization used in the 2nd stage.
Zu 0,6 mol SOCl2 werden portionsweise 0,1 mol 2-Hydroxymethyl- nicotinsäureamid (allgemeine Formel 3) gegeben. Anschließen wird 30 min unter Rückfluss erhitzt und das überschüssige SOCl2 abdestilliert. Zum festen Rückstand werden nacheinander Wasser und 10% NaOH unter Kühlung zugetropft (pH 9). Das Reaktionsprodukt, 2-Chlormethyl-nicotinsäureamid (allgemeine Formel 2), wird abgesaugt, mit Wasser und Ethanol gewaschen und für die 3. Stufe verwendet.0.1 mol of 2-hydroxymethyl nicotinamide (general formula 3) is added in portions to 0.6 mol of SOCl 2 . The mixture is then heated under reflux for 30 min and the excess SOCl 2 is distilled off. Water and 10% NaOH are added dropwise to the solid residue with cooling (pH 9). The reaction product, 2-chloromethyl-nicotinamide (general formula 2), is suctioned off, washed with water and ethanol and used for the 3rd stage.
0,1 mol 2-Chlormethyl-nicotinsäureamid (allgemeine Formel 2) und 0,2 mol K2CO3 werden in DMF bei 120°C 4 Stunden unter Rühren erhitzt. Anschließend wird auf Zimmertemperatur abgekühlt und das K2CO3 abgesaugt. Das DMF wird bei 90°C abdestilliert und der Rückstand mit Isopropanol verrührt. Das Pyrrolo[3,4-b]pyridin- 5-on (allgemeine Formel 1) wird abgesaugt und aus Ethanol oder Isopropanol umkristallisiert. 0.1 mol of 2-chloromethyl-nicotinamide (general formula 2) and 0.2 mol of K 2 CO 3 are heated in DMF at 120 ° C. for 4 hours with stirring. It is then cooled to room temperature and the K 2 CO 3 is suctioned off. The DMF is distilled off at 90 ° C. and the residue is stirred with isopropanol. The pyrrolo [3,4-b] pyridin-5-one (general formula 1) is filtered off and recrystallized from ethanol or isopropanol.
Beispiele für die synthetisierten Verbindungen sind in Tab. 2 zusammengestellt.Examples of the synthesized compounds are summarized in Tab. 2.
Claims (17)
worin
R1 = (C1-C3)alkyl, (C1-C2)alkoxy, Trifluormethyl oder Halogen und
n = 1-3 ist.1. New compounds of the general formula 1
wherein
R 1 = (C 1 -C 3 ) alkyl, (C 1 -C 2 ) alkoxy, trifluoromethyl or halogen and
n = 1-3.
6-(4-Methylbenzyl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-on
6-(4-Methoxybenzyl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-on
6-(4-Chlorbenzyl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-on
6-(3-Chlorbenzyl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-on
6-(2-Chlorbenzyl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-on
6-(4-Fluorbenzyl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-on
6-(2-Fluorbenzyl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-on
6-(2,6-Difluorbenzyl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-on
6-(2-Trifluormethylbenzyl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-on.2. Compounds of general formula 1 according to claim 1:
6- (4-methylbenzyl) -6,7-dihydro-5H-pyrrolo [3,4-b] pyridin-5-one
6- (4-methoxybenzyl) -6,7-dihydro-5H-pyrrolo [3,4-b] pyridin-5-one
6- (4-chlorobenzyl) -6,7-dihydro-5H-pyrrolo [3,4-b] pyridin-5-one
6- (3-chlorobenzyl) -6,7-dihydro-5H-pyrrolo [3,4-b] pyridin-5-one
6- (2-chlorobenzyl) -6,7-dihydro-5H-pyrrolo [3,4-b] pyridin-5-one
6- (4-fluorobenzyl) -6,7-dihydro-5H-pyrrolo [3,4-b] pyridin-5-one
6- (2-fluorobenzyl) -6,7-dihydro-5H-pyrrolo [3,4-b] pyridin-5-one
6- (2,6-difluorobenzyl) -6,7-dihydro-5H-pyrrolo [3,4-b] pyridin-5-one
6- (2-trifluoromethylbenzyl) -6,7-dihydro-5H-pyrrolo [3,4-b] pyridin-5-one.
3. Process for the preparation of 6,7-dihydro-pyrrolo [3,4-b] pyridin-5-ones of the general formula 1, characterized in that compounds of the general formula 2, in which R 1 and n have the meaning given , cyclized in the presence of a solvent containing an HCl-affine component.
5. A process for the preparation of 6,7-dihydro-pyrrolo [3,4-b] pyridin-5-ones of the general formula 1, characterized in that compounds of the general formula 2 by reacting compounds of the general formula 3, in which R 1 and n have the meaning given, with chlorinating agents.
7. Process for the preparation of 6,7-dihydro-pyrrolo [3,4-b] pyridin-5-ones of the general formula 1, characterized in that compounds of the general formula 3 by heating compounds of the general formula 4, in which R 1 and n have the meaning given, and 5 is obtained in a solvent.
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DE10042093A DE10042093A1 (en) | 2000-08-26 | 2000-08-26 | Anticonvulsant 6,7-dihydro-pyrrolo [3,4-d] pyridin-5-ones and process for their preparation |
AU2001285905A AU2001285905A1 (en) | 2000-08-26 | 2001-08-24 | 6,7-dihydro-pyrrolo(3,4-b)pyridin-5-ones with an anticonvulsive action and methods for producing the same |
PCT/EP2001/009810 WO2002018381A1 (en) | 2000-08-26 | 2001-08-24 | 6,7-dihydro-pyrrolo[3,4-b]pyridin-5-ones with an anticonvulsive action and methods for producing the same |
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WO2013071201A1 (en) | 2011-11-11 | 2013-05-16 | Vanderbilt University | Substituted benzylspiroindolin-2-one analogs as positive allosteric modulators of the muscarinic acetylcholine receptor m1 |
US9029563B2 (en) | 2012-01-06 | 2015-05-12 | Vanderbilt University | Substituted 1-benzylindolin-2-one analogs as positive allosteric modulators of muscarinic acetylcholine M1 receptors |
US9012445B2 (en) | 2012-01-12 | 2015-04-21 | Vanderbilt University | Substituted 4-(1H-pyrazol-4-yl)benzyl analogues as positive allosteric modulators of mAChR M1 receptors |
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2000
- 2000-08-26 DE DE10042093A patent/DE10042093A1/en not_active Withdrawn
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2001
- 2001-08-24 AU AU2001285905A patent/AU2001285905A1/en not_active Abandoned
- 2001-08-24 WO PCT/EP2001/009810 patent/WO2002018381A1/en active Application Filing
Patent Citations (5)
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DE2251559A1 (en) * | 1971-10-22 | 1973-04-26 | Rhone Poulenc Sa | NEW PYRROLO SQUARE BRACKET ON 3.4 SQUARE BRACKET ON PYRIDINE DERIVATIVES, THEIR MANUFACTURING AND THE MEDICAL COMPOSITIONS THAT CONTAIN THEM |
DE2615067A1 (en) * | 1975-04-07 | 1976-10-28 | Rhone Poulenc Ind | NEW HETEROCYCLIC COMPOUNDS, THEIR PRODUCTION AND COMPOSITIONS THEREOF |
WO1992012153A1 (en) * | 1989-10-05 | 1992-07-23 | American Home Products Corporation | Novel antihypertensive benzopyran derivatives |
EP0530444A1 (en) * | 1991-08-01 | 1993-03-10 | American Cyanamid Company | Aryl, amide, imide, and carbamate pyridine antagonists of platelet activating factor |
WO1995034563A1 (en) * | 1994-06-16 | 1995-12-21 | Pfizer Inc. | Pyrazolo and pyrrolopyridines |
Non-Patent Citations (1)
Title |
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GUTKOWSKA,Bozenna, et.al.: Synthesis of some N-substituted 1-oxo-4-azaindolines. In: Acta Pol. Pharm., 1987, 44 (2), S.242-244, zitiert als Chemical Abstract 1988, Vol.109, Nr.230834 * |
Also Published As
Publication number | Publication date |
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WO2002018381A1 (en) | 2002-03-07 |
AU2001285905A1 (en) | 2002-03-13 |
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