DD274218A1 - PROCESS FOR PREPARING 2-CARBALKOXY-METHYL-4-PHENYL-1,2-DIHYDRO-1-OXO-PHTHALAZINES - Google Patents
PROCESS FOR PREPARING 2-CARBALKOXY-METHYL-4-PHENYL-1,2-DIHYDRO-1-OXO-PHTHALAZINES Download PDFInfo
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- DD274218A1 DD274218A1 DD31826788A DD31826788A DD274218A1 DD 274218 A1 DD274218 A1 DD 274218A1 DD 31826788 A DD31826788 A DD 31826788A DD 31826788 A DD31826788 A DD 31826788A DD 274218 A1 DD274218 A1 DD 274218A1
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Abstract
Die Erfindung betrifft ein Verfahren zur Herstellung von 2-Carbalkoxy-methyl-1,2-dihydro-1-oxo-phthalazinen mit unterschiedlich substituiertem Phenylring in 4-Stellung in jeweils einstufiger Synthese. Derartige biologisch aktive Verbindungen koennen Bedeutung als Pharmaka erlangen. Formel IThe invention relates to a process for the preparation of 2-carbalkoxy-methyl-1,2-dihydro-1-oxo-phthalazines with differently substituted phenyl ring in the 4-position in each one-step synthesis. Such biologically active compounds can gain importance as pharmaceuticals. Formula I
Description
wobei R2 und R3 die vorstehend genannte Bedeutung besitzen, unter rückfließendem Erhitzen mit a-Hydrazinoessigsäurealkylestersalzen der allgemeinen Formel III,wherein R 2 and R 3 have the abovementioned meaning, with refluxing heating with a-Hydrazinoessigsäurealkylestersalzen the general formula III,
HX · H2N-NH-CH2-COOR1 IIIHX.H 2 N-NH-CH 2 -COOR 1 III
wobei R1 die obengenannte Bedeutung hat und X ein anorganischer Säurerest ist, in Alkanolen, vorwiegend C1-C4, umgesetzt werden.wherein R 1 has the abovementioned meaning and X is an inorganic acid radical, in alkanols, predominantly C 1 -C 4 , are reacted.
2. Verfahren nach Anspruch 1, dadurch gekennzeichnet, daß als Hilfsbase tertiäre Amine, z.B. Triethylamin, in mindestens äquimolarer Menge eingesetzt werden.2. The method according to claim 1, characterized in that as auxiliary base tertiary amines, e.g. Triethylamine, be used in at least equimolar amount.
Die Erfindung betrifft ein Verfahren zur Herstellung von 2-Carbalkoxy-methyl-4-phenyl-1,2-dihydro-i-oxo-phthalazinen der allgemeinen Formel I. Die Verbindungen sind biologisch aktiv und können als Pharmaka Bedeutung erlangen.The invention relates to a process for the preparation of 2-carbalkoxy-methyl-4-phenyl-1,2-dihydro-i-oxo-phthalazines of the general formula I. The compounds are biologically active and can obtain significance as pharmaceuticals.
Charakteristik der bekannten technischen LösungenCharacteristic of the known technical solutions
Verbindungen der allgemeinen Formel I sind weder in der Patent- noch in der chemischen Fachliteratur beschrieben. In einem rumänischen Patent (Cilianu-Bibian, S., A.Cirstea, M. Petrovanu, E.Rucinschi, I.Drutä, M.Caprosu, I.Ciocoiu und A. Mihalcea, Rom RO 87,512 [Cl.C07 D 237/14], 30 Sep 1985, Appl. 112,805,09 Dec 1983) wurden lediglich durch Umsetzung von 4-(4-Bromphenyl)-1,2-dihydro-1-oxo-pyridazin mit entsprechenden a-Bromessigsäurealkylestern in Ggw. von Kaliumcarbonat hergestellte 2-Carbalkoxy-4-(4-bromphenyl)-1,2-dihydro-1-oxo-pyridazine sowie deren antikonvulsive Wirkung niedergelegt.Compounds of general formula I are described neither in the patent nor in the chemical literature. In a Romanian patent (Cilianu-Bibian, S., A.Cirstea, M. Petrovanu, E.Rucinschi, I.Drutä, M.Caprosu, I.Ciocoiu and A. Mihalcea, Rome RO 87,512 [Cl.C07 D 237 / 14], Sep. 30, 1985, Appl., 112, 805, 09 Dec, 1983) were prepared merely by reacting 4- (4-bromophenyl) -1,2-dihydro-1-oxopyridazine with corresponding alkyl α-bromoacetic acid esters in percent by weight of potassium carbonate 2-Carbalkoxy-4- (4-bromophenyl) -1,2-dihydro-1-oxo-pyridazines and their anticonvulsive effect laid down.
Ziel der ErfindungObject of the invention
Ziel der Erfindung ist es, derartige Verbindungen aus leicht zugänglichen Ausgangsmaterialien in einfacher Weise und mit hohen Ausbeuten herzustellen.The aim of the invention is to produce such compounds from readily available starting materials in a simple manner and with high yields.
Aufgabe der Erfindung ist es, einen technisch anwendbaren Syntheseweg zur Herstellung von 2-Carbalkoxy-methyl-4-phenyl-1,2-dihydro-1 -ι >xo-phthalazinen der allgemeinen Formel I aufzufinden.The object of the invention is to find a technically applicable synthesis route for the preparation of 2-carbalkoxymethyl-4-phenyl-1,2-dihydro-1-xaxophthalazines of the general formula I.
Erfindungsgemäß wird die Aufgabe zur Darstellung der Verbindungen der allgemeinen Formel I dadurch gelöst, daß ß-Benzoylbenzoesäuren dsr allgemeinen Forme! II,According to the invention the object for the preparation of the compounds of general formula I is achieved in that ß-Benzoylbenzoesäuren dsr general forms! II
wobei R2 = H, Alkyl, Alkoxy, N(CH3I2, F, Cl. Br, I undwherein R 2 = H, alkyl, alkoxy, N (CH 3 I 2 , F, Cl. Br, I and
R3 = H, NO2, F, Cl, Br bedeuten, unter rückfließendem Erhitzen mit a-Hydrazinoessigsäurealkylestersalzen der allgemeinen Formel III,R 3 = H, NO 2 , F, Cl, Br, with refluxing heating with a-Hydrazinoessigsäurealkylestersalzen the general formula III,
HX · H2N-NH-CH2-COOR1 IIIHX.H 2 N-NH-CH 2 -COOR 1 III
wobei R' gleich niedrig Alkyl (C)-C4) un IX ein anorganischer Säurerest ist, zur Reaktion gebracht werden und durch Einrühren in Wasser und anschließendes Aufbewahren der Reaktionsmischung die Kristallisation vervollständigt wird.wherein R 'is the same low alkyl (C) -C 4 ) and un IX an inorganic acid radical, are reacted and by stirring in water and then storing the reaction mixture, the crystallization is completed.
Die Erfindung soll nachstehend an 4 Ausführungsbeispielen näher erläutert werden.The invention will be explained in more detail below with reference to 4 exemplary embodiments.
2-Carbethoxy-methyl-4-phenyl-1,2-dihydro-1-oxo-phthalazin I; R1 = C2H5, R2 = R1 = H 4,5g ß-Benzoylbenzoesäure (II; R2 = R3 = H) werden in 21 ml Ethanol gelöst, mit 3,1 π α-Hydrazinoessigsäureethylester · HCI (III; R1 = C2H61X = Cl) sowie 3,0ml Triethylamin versetzt und 2,5h rückfließend erhitzt. Nachdem Abkühlen wird in 10OmI Wasser eingerührt und bei 0-50C aufbewahrt. Anschließend wird der Niederschlag abgesaugt, mit Wasser gewaschen und getrocknet.2-Carbethoxy-methyl-4-phenyl-1,2-dihydro-1-oxo-phthalazine I; R 1 = C 2 H 5 , R 2 = R 1 = H 4.5 g of β-benzoylbenzoic acid (II; R 2 = R 3 = H) are dissolved in 21 ml of ethanol, containing 3.1 π α-hydrazinoacetate · HCl ( III, R 1 = C 2 H 61 X = Cl) and 3.0 ml of triethylamine were added and refluxed for 2.5 h. After cooling, stirred in 10OmI of water and stored at 0-5 0 C. The precipitate is then filtered off with suction, washed with water and dried.
Schmb.: 183-1860C (Ethanol), Ausbeute: 71%.Schmb .: 183-186 0 C (ethanol), yield: 71%.
2-Carbethoxy-methyl-4-(4-methoxyphenyi)-1,2-dihydro-1-oxo-phthalazin I; R1 = C2H6, R2 = 4-OCH3, R3 = H Zur Herstellung der Verbindung wird wie unter Beispiel 1 beschrieben verfahren.2-Carbethoxy-methyl-4- (4-methoxyphenyl) -1,2-dihydro-1-oxo-phthalazine I; R 1 = C 2 H 6 , R 2 = 4-OCH 3 , R 3 = H For the preparation of the compound as described in Example 1 procedure.
Schmb.: 173-1760C (Ethanol), Ausbeute: 67%.Schmb.: 173-176 0 C (ethanol), yield: 67%.
2-Carbethoxy-methyl-4(4-bromphenyl)-1,2-dihydro-1-oxo-phthalazin I; R1 = C2H5, R2 = 4-Br, R3 = H Zur Herstellung der Verbindung wird wie unter Beispiel 1 und 2 beschrieben verfahren.2-Carbethoxy-methyl-4 (4-bromophenyl) -1,2-dihydro-1-oxo-phthalazine I; R 1 = C 2 H 5 , R 2 = 4-Br, R 3 = H For the preparation of the compound as described in Example 1 and 2 described method.
Schmb.: ab 151,50C (Dioxan/Wasser 1:1,5 (v/v](, Ausbeute: 69%.Schmb .: from 151.5 0 C (dioxane / water 1: 1.5 (v / v] (Yield: 69%.
2-Carbethoxy-methyl-4-phenyl-1,2-dihydro-1-oxo-6-nitro-phthalazin I; R1 = C2H5, R2 = H, R3 = 6-NO2 Zur Herstellung der Verbindung wird wie unter Beispiel 1,2 und 3 beschrieben verfahren. Schmb.: ab 90,50C (2C%iges Ethanol), Ausbeute: 74%.2-Carbethoxy-methyl-4-phenyl-1,2-dihydro-1-oxo-6-nitro-phthalazine I; R 1 = C 2 H 5 , R 2 = H, R 3 = 6-NO 2 To prepare the compound, the procedure is as described in Example 1,2 and 3. Mb: from 90.5 0 C (2C% ethanol), yield: 74%.
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DD31826788A DD274218A1 (en) | 1988-07-25 | 1988-07-25 | PROCESS FOR PREPARING 2-CARBALKOXY-METHYL-4-PHENYL-1,2-DIHYDRO-1-OXO-PHTHALAZINES |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DD31826788A DD274218A1 (en) | 1988-07-25 | 1988-07-25 | PROCESS FOR PREPARING 2-CARBALKOXY-METHYL-4-PHENYL-1,2-DIHYDRO-1-OXO-PHTHALAZINES |
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| DD274218A1 true DD274218A1 (en) | 1989-12-13 |
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| DD31826788A DD274218A1 (en) | 1988-07-25 | 1988-07-25 | PROCESS FOR PREPARING 2-CARBALKOXY-METHYL-4-PHENYL-1,2-DIHYDRO-1-OXO-PHTHALAZINES |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6020379A (en) * | 1999-02-19 | 2000-02-01 | Cell Pathways, Inc. | Position 7 substituted indenyl-3-acetic acid derivatives and amides thereof for the treatment of neoplasia |
| US6077842A (en) * | 1998-11-24 | 2000-06-20 | Cell Pathways, Inc. | Method of inhibiting neoplastic cells with pyrazolopyridylpyridazinone derivatives |
| US6232312B1 (en) | 1995-06-07 | 2001-05-15 | Cell Pathways, Inc. | Method for treating patient having precancerous lesions with a combination of pyrimidopyrimidine derivatives and esters and amides of substituted indenyl acetic acides |
-
1988
- 1988-07-25 DD DD31826788A patent/DD274218A1/en active IP Right Grant
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6232312B1 (en) | 1995-06-07 | 2001-05-15 | Cell Pathways, Inc. | Method for treating patient having precancerous lesions with a combination of pyrimidopyrimidine derivatives and esters and amides of substituted indenyl acetic acides |
| US6077842A (en) * | 1998-11-24 | 2000-06-20 | Cell Pathways, Inc. | Method of inhibiting neoplastic cells with pyrazolopyridylpyridazinone derivatives |
| US6020379A (en) * | 1999-02-19 | 2000-02-01 | Cell Pathways, Inc. | Position 7 substituted indenyl-3-acetic acid derivatives and amides thereof for the treatment of neoplasia |
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