CH558319A - 2-(carboxy-phenyl-carbamoyl)-cyclohexane-1,3-diones - prepd by saponifying corresp. lower alkyl carboxylate - Google Patents
2-(carboxy-phenyl-carbamoyl)-cyclohexane-1,3-diones - prepd by saponifying corresp. lower alkyl carboxylateInfo
- Publication number
- CH558319A CH558319A CH1763171A CH1763171A CH558319A CH 558319 A CH558319 A CH 558319A CH 1763171 A CH1763171 A CH 1763171A CH 1763171 A CH1763171 A CH 1763171A CH 558319 A CH558319 A CH 558319A
- Authority
- CH
- Switzerland
- Prior art keywords
- lower alkyl
- group
- lower alkoxy
- prepd
- formula
- Prior art date
Links
- DJNUASZTOQQWHM-UHFFFAOYSA-N (2,6-dioxocyclohexanecarbonyl)-phenylcarbamic acid Chemical class C(=O)(O)N(C(=O)C1C(CCCC1=O)=O)C1=CC=CC=C1 DJNUASZTOQQWHM-UHFFFAOYSA-N 0.000 title 1
- 125000005599 alkyl carboxylate group Chemical group 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 19
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
- 125000002950 monocyclic group Chemical group 0.000 claims abstract description 9
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 8
- 150000002367 halogens Chemical class 0.000 claims abstract description 8
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 7
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 7
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 5
- 125000003118 aryl group Chemical group 0.000 claims abstract description 4
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 3
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 150000002431 hydrogen Chemical group 0.000 claims description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 239000011593 sulfur Chemical group 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 239000000460 chlorine Chemical group 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 1
- 230000001857 anti-mycotic effect Effects 0.000 abstract description 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 230000000844 anti-bacterial effect Effects 0.000 abstract 1
- 229910052740 iodine Inorganic materials 0.000 abstract 1
- 238000007127 saponification reaction Methods 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- -1 tetrahydrofuran Chemical class 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 230000002401 inhibitory effect Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- LXSQXZSCSVVJGM-UHFFFAOYSA-N OC(CC(C=CC(N=C=O)=C1)=C1Cl)=O Chemical compound OC(CC(C=CC(N=C=O)=C1)=C1Cl)=O LXSQXZSCSVVJGM-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 229940127089 cytotoxic agent Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Cpds. of formula (I) (where X is O or S; R1 is H, Cl, Br, I, lower alkyl, acetyl, lower alkoxy, NO2 or di-(lower alkyl) -amino; R2 is H, monocyclic aryl or monocyclic O- or S-heterocycle, aryls and heterocycles being opt. substd. by halogen, lower alkyl, lower alkoxy or NO2; R3 is as R2 excluding H; when R2 is not H, R2 and R3 are the same, or R2 and R3 are both H) are prepd. by the saponification of a cpd. (II) pref. with dil. aqs. alkali (where R4 is lower alkyl). I show antibacterial effect in concns. of 0.2-50 ug/ml and antimycotic activity in concns. of 0.3-50 ug/ml.
Description
Die Erfindung betrifft ein Verfahren zur Herstellung neuer 1,3-Diketone der Formel I (siehe Formalblatt), worin X für Sauerstoff oder Schwefel, Rl für Wasserstoff, Chlor, Brom, Jod, Fluor, eine niedere Alkylgruppe, die Acetylgruppe, eine niedere Alkoxygruppe, die Nitrogruppe oder eine
EMI1.1
Gruppe, wobei R eine niedere Alkylgruppe bedeutet, R2 für Wasserstoff, eine monocyclische unsubstituierte oder durch Halogen, eine niedere Alkyl-, niedere Alkoxy- oder die Nitrogruppe substituierte Arylgruppe oder für einen monocyclischen unsubstituierten oder durch Halogen, eine niedere Alkyl-, niedere Alkoxy- oder die Nitrogruppe substituierten Heterocyclus mit Sauerstoff oder Schwefel als Heteroatome und R3 für eine monocyclische unsubstituierte oder durch Halogen, eine niedere Alkyl-,
niedere Alkoxy- oder die Nitrogruppe substituierte Arylgruppe oder für einen monocyclischen unsubstituierten oder durch Halogen, eine niedere Alkyl-, niedere Alkoxy- oder die Nitrogruppe substituierten Heterocyclus mit Sauerstoff oder Schwefel als Heteroatome stehen, und R2 und R3, wenn R2 nicht für Wasserstoff steht, stets gleich sind, oder R2 und R3 je für Wasserstoff stehen.
Erfindungsgemäss gelangt man zu den neuen Verbindungen der Formel I, indem man Verbindungen der Formel II, worin X, R,, R2 und R3 obige Bedeutung besitzen und R4 für eine niedere Alkylgruppe steht, verseift.
Das erfindungsgemässe Verfahren kann beispielsweise durchgeführt werden, indem man eine Verbindung der Formel II mit einem basischen Verseifungsmittel, z. B. mit verdünntem wässrigem Natriumhydroxid behandelt. Aus dem Reaktionsgemisch kann das Verfahrensprodukt nach an sich bekannten Methoden isoliert und gewünschtenfalls gereinigt werden, z. B. durch Versetzen mit Säure und Umkristallisation.
Die durch R1, R2, R3 und R4 symbolisierten niederen Alkylgruppen bestehen vorzugsweise aus 1 bis 4 Kohlenstoffatomen und bedeuten insbesondere die Methylgruppe. Die durch R2 und R3 symbolisierte Arylgruppe besitzt vorzugsweise 5 bis 6 Ringglieder.
Die als Ausgangsprodukte benötigten Verbindungen der Formel II können erhalten werden, indem man eine Verbindung der Formel III, worin R2 und R3 obige Bedeutung besitzen und Me für ein Alkalimetall steht, mit einer Verbindung der Formel IV, worin X, R, und R4 obige Bedeutung besitzen, umsetzt.
Dabei kann man beispielsweise folgendermassen vorgehen: Zu der Aufschlämmung einer Verbindung der Formel III in einem unter den Reaktionsbedingungen inerten Lösungsmittel, z. B. in einem cyclischen Äther wie Tetrahydrofuran, setzt man eine Verbindung der Formel IV zu und lässt bei erhöhter Temperatur, vorzugsweise bei der Siedetemperatur des Reaktionsgemisches reagieren. Nach Beendigung der Reaktion, z. B. nach 2 bis 10 Stunden, vorzugsweise nach 3 bis 6 Stunden, isoliert man das Reaktionsprodukt nach an sich bekannten Methoden, z. B. durch Versetzen mit einer Säure, Abfiltrieren des Niederschlags und Trocknen im Vakuum. Anschliessend kann es noch gegebenenfalls gereinigt werden, z. B. durch Umkristallisation aus einem geeigneten Lösungsmittel.
Soweit die Herstellung der Ausgangsprodukte nicht beschrieben wird, sind diese bekannt oder nach an sich bekannten Verfahren bzw. analog zu den hier beschriebenen oder analog zu an sich bekannten Verfahren herstellbar.
Die Verbindungen der Formel I und gegebenenfalls ihre pharmakologisch verträglichen Salze besitzen bei geringer Toxizität interessante pharmakodynamische Eigenschaften und können daher als Heilmittel verwendet werden. Sie stellen wertvolle Chemotherapeutika dar und entfalten ihre Hemmwirkung gegen Bakterien bei minimalen Hemmkonzentrationen zwischen 0,2-50 Lg/ml. Weiter zeigen die erfindungsgemässen Substanzen auch eine antimykotische Wirksamkeit, die sich bei minimalen Hemmkonzentrationen zwischen etwa 0,3-50,ug/ml manifestiert.
Im folgenden Beispiel, das die Erfindung näher erläutern, ihren Umfang aber in keiner Weise einschränken soll, erfol gen alle Temperaturangaben in Celsiusgraden.
Beispiel 2-(4-Carboxy-3 -chlorphenyl)-carbamoyl-5-methyl- cyclohexadion-1,3
11,26 g 2-(4-Carbomethoxy-3 -chlorphenyl) -carbamoyl5-methylcyclohexandion-1,3 werden mit 140 ml 0,5 N wässriger Natriumhydroxidlösung 5 Stunden bei Zimmertemperatur gerührt. Dann wird mit konzentrierter Salzsäure angesäuert und die im Titel genannte Verbindung abgenutscht, bei 100 im Vakuum getrocknet und aus Eisessig umkristallisiert. Schmp. 245-260 (Zers.).
Das als Ausgangsprodukt benötigte 2-(4-Carbomethoxy 3 -chlorphenyl) -carb amoyl-5 -methylcyclohexandion- 1,3 kann folgendermassen erhalten werden:
Eine Aufschlämmung von 14,8 g 5-Methyldihydroresorcin Natriumsalz in 200 ml absolutem Tetrahydrofuran wird mit 23 g (4-Carboxymethyl-3 -chlorphenyl)-isocyanat versetzt und das Gemisch 5 Stunden unter Feuchtigkeitsausschluss am Rückfluss erhitzt. Anschliessend wird das Lösungsmittel unter vermindertem Druck abdestilliert, der Rückstand zerkleinert und in 1500 ml Wasser eingetragen. Das Gemisch wird 15 Minuten gekocht, heiss filtriert und das Filtrat mit konzentrierter Salzsäure angesäuert. Nach dem Abkühlen wird der Niederschlag abgenutscht, gewaschen und getrocknet. Nach Umkristallisieren aus Propanol-1 schmilzt die Verbindung bei 155-158 .
EMI1.2
The invention relates to a process for the production of new 1,3-diketones of the formula I (see form sheet), in which X is oxygen or sulfur, Rl is hydrogen, chlorine, bromine, iodine, fluorine, a lower alkyl group, the acetyl group, a lower alkoxy group , the nitro group or a
EMI1.1
Group, where R denotes a lower alkyl group, R2 denotes hydrogen, a monocyclic unsubstituted or aryl group substituted by halogen, a lower alkyl, lower alkoxy or nitro group, or a monocyclic unsubstituted or halogen, lower alkyl, lower alkoxy group or the nitro group substituted heterocycle with oxygen or sulfur as heteroatoms and R3 for a monocyclic unsubstituted or halogen, a lower alkyl,
lower alkoxy or nitro group or a monocyclic unsubstituted or halogen, lower alkyl, lower alkoxy or nitro group substituted heterocycle with oxygen or sulfur as heteroatoms, and R2 and R3, if R2 is not hydrogen, are always the same, or R2 and R3 each represent hydrogen.
According to the invention, the new compounds of the formula I are obtained by saponifying compounds of the formula II in which X, R 1, R 2 and R 3 have the above meanings and R 4 represents a lower alkyl group.
The inventive method can be carried out, for example, by treating a compound of the formula II with a basic saponifying agent, e.g. B. treated with dilute aqueous sodium hydroxide. The process product can be isolated from the reaction mixture by methods known per se and, if desired, purified, e.g. B. by adding acid and recrystallization.
The lower alkyl groups symbolized by R1, R2, R3 and R4 preferably consist of 1 to 4 carbon atoms and are in particular the methyl group. The aryl group symbolized by R2 and R3 preferably has 5 to 6 ring members.
The compounds of the formula II required as starting materials can be obtained by combining a compound of the formula III, in which R2 and R3 have the above meaning and Me is an alkali metal, with a compound of the formula IV in which X, R and R4 have the above meaning own, implements.
You can proceed as follows, for example: To the suspension of a compound of the formula III in a solvent which is inert under the reaction conditions, e.g. B. in a cyclic ether such as tetrahydrofuran, a compound of formula IV is added and allowed to react at an elevated temperature, preferably at the boiling point of the reaction mixture. After completion of the reaction, e.g. B. after 2 to 10 hours, preferably after 3 to 6 hours, the reaction product is isolated by methods known per se, for. B. by adding an acid, filtering off the precipitate and drying in vacuo. It can then be cleaned if necessary, e.g. B. by recrystallization from a suitable solvent.
If the production of the starting products is not described, these are known or can be produced by processes known per se or analogously to those described here or analogously to processes known per se.
The compounds of the formula I and, if appropriate, their pharmacologically acceptable salts have interesting pharmacodynamic properties with low toxicity and can therefore be used as medicaments. They are valuable chemotherapeutic agents and develop their inhibitory effect against bacteria at minimal inhibitory concentrations between 0.2-50 μg / ml. The substances according to the invention also show an antimycotic activity which manifests itself at minimal inhibitory concentrations between about 0.3-50 μg / ml.
In the following example, which explains the invention in more detail, but is not intended to limit its scope in any way, all temperatures are given in degrees Celsius.
Example 2- (4-Carboxy-3-chlorophenyl) -carbamoyl-5-methyl-cyclohexadione-1,3
11.26 g of 2- (4-carbomethoxy-3-chlorophenyl) -carbamoyl-5-methylcyclohexanedione-1,3 are stirred with 140 ml of 0.5 N aqueous sodium hydroxide solution for 5 hours at room temperature. It is then acidified with concentrated hydrochloric acid and the compound mentioned in the title is suction filtered, dried at 100 in vacuo and recrystallized from glacial acetic acid. M.p. 245-260 (dec.).
The 2- (4-carbomethoxy 3-chlorophenyl) -carbamoyl-5 -methylcyclohexanedione-1,3 required as a starting product can be obtained as follows:
23 g of (4-carboxymethyl-3-chlorophenyl) isocyanate are added to a suspension of 14.8 g of 5-methyldihydroresorcinol sodium salt in 200 ml of absolute tetrahydrofuran, and the mixture is refluxed for 5 hours with exclusion of moisture. The solvent is then distilled off under reduced pressure, the residue is comminuted and introduced into 1500 ml of water. The mixture is boiled for 15 minutes, filtered while hot and the filtrate is acidified with concentrated hydrochloric acid. After cooling, the precipitate is filtered off with suction, washed and dried. After recrystallization from 1-propanol, the compound melts at 155-158.
EMI1.2
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1763171A CH558319A (en) | 1971-12-03 | 1971-12-03 | 2-(carboxy-phenyl-carbamoyl)-cyclohexane-1,3-diones - prepd by saponifying corresp. lower alkyl carboxylate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1763171A CH558319A (en) | 1971-12-03 | 1971-12-03 | 2-(carboxy-phenyl-carbamoyl)-cyclohexane-1,3-diones - prepd by saponifying corresp. lower alkyl carboxylate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH558319A true CH558319A (en) | 1975-01-31 |
Family
ID=4426880
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1763171A CH558319A (en) | 1971-12-03 | 1971-12-03 | 2-(carboxy-phenyl-carbamoyl)-cyclohexane-1,3-diones - prepd by saponifying corresp. lower alkyl carboxylate |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH558319A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0126713A3 (en) * | 1983-05-18 | 1985-04-17 | Ciba-Geigy Ag | Cyclohexanedione-carboxylic-acid derivatives having a herbicidal and plant growth regulating activity |
| US4803268A (en) * | 1984-10-02 | 1989-02-07 | Ciba-Geigy Corporation | Process for the preparation of cyclohexanedionecarboxylic acid derivatives |
-
1971
- 1971-12-03 CH CH1763171A patent/CH558319A/en not_active IP Right Cessation
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0126713A3 (en) * | 1983-05-18 | 1985-04-17 | Ciba-Geigy Ag | Cyclohexanedione-carboxylic-acid derivatives having a herbicidal and plant growth regulating activity |
| US4693745A (en) * | 1983-05-18 | 1987-09-15 | Ciba-Geigy Corporation | Cyclohexanedionecarboxylic acid derivatives with herbicidal and plant growth regulating properties |
| US4803268A (en) * | 1984-10-02 | 1989-02-07 | Ciba-Geigy Corporation | Process for the preparation of cyclohexanedionecarboxylic acid derivatives |
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| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |