DE2608697A1 - NEW ORGANIC COMPOUNDS, THEIR PRODUCTION AND USE - Google Patents
NEW ORGANIC COMPOUNDS, THEIR PRODUCTION AND USEInfo
- Publication number
- DE2608697A1 DE2608697A1 DE19762608697 DE2608697A DE2608697A1 DE 2608697 A1 DE2608697 A1 DE 2608697A1 DE 19762608697 DE19762608697 DE 19762608697 DE 2608697 A DE2608697 A DE 2608697A DE 2608697 A1 DE2608697 A1 DE 2608697A1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- compounds
- carbon atoms
- alkyl
- lower alkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
- C07D307/83—Oxygen atoms
Description
SANDOZ-PATENT-GMBHSANDOZ-PATENT-GMBH
7850 Lörrach Case 100-43187850 Loerrach Case 100-4318
Neue organische Verbindungen, ihre Herstellung und VerwendungNew organic compounds, their production and uses
Die Erfindung betrifft neue Verbindungen der Formel I (siehe Formelblatt), worin R. für Alkyl mit 1 bis 10 Kohlenstoffatomen, Cycloalkyl mit 3 bis 8 Kohlenstoffatomen oder Phenyl, R_ für Wasserstoff oder Niederalkyl und R3 für Halogen, Nitro, Niederalkyl, Methylthio, Hydroxy, Niederalkoxy, Äcyloxy oder Acylamino stehen, wobei R_ nicht Wasserstoff bedeuten kann, wenn R_ sich in Stellung 5 befindet, und wenn R1 und R_ für eine gradlinige Alkylkette von 1 bis 5 Kohlenstoffatomen stehen und identisch sind, sowie Verfahren zu deren Herstellung.The invention relates to new compounds of the formula I (see formula sheet), in which R. for alkyl with 1 to 10 carbon atoms, cycloalkyl with 3 to 8 carbon atoms or phenyl, R_ for hydrogen or lower alkyl and R 3 for halogen, nitro, lower alkyl, methylthio, Hydroxy, lower alkoxy, acyloxy or acylamino, where R_ cannot mean hydrogen when R_ is in position 5, and when R 1 and R_ stand for a straight alkyl chain of 1 to 5 carbon atoms and are identical, as well as processes for their preparation.
Erfindungsgemäss gelangt man zu den neuen Verbindungen der Formel I, indem man Verbindungen der Formel II, worin R., R3 und R3 obige Bedeutung haben, lactonisiert.According to the invention, the new compounds of the formula I are obtained by lactonizing compounds of the formula II in which R., R 3 and R 3 have the above meanings.
609839/1021 ORIGINAL INSPECTED609839/1021 ORIGINAL INSPECTED
- 2 - Case 100-4318- 2 - Case 100-4318
Falls R Cycloalkyl bedeutet, so enthält dieser Rest vorzugsweise 5 bis 7 Kohlenstoffatome und stellt insbesondere Cyclopentyl oder Cyclohexyl dar. Falls R, Alkyl bedeutet, so enthält dieser vorzugsweiseIf R is cycloalkyl, this radical preferably contains 5 to 7 carbon atoms and represents in particular cyclopentyl or cyclohexyl. If R 1 denotes alkyl, this preferably contains
3 bis 6, insbesondere 3 oder 4, Kohlenstoffatome und ist vorzugsweise verzweigt und stellt insbesondere Isobutyl oder Isopropyl dar.3 to 6, especially 3 or 4, carbon atoms and is preferably branched and is in particular isobutyl or isopropyl.
Bedeutet R„ Niederalkyl, so enthält dieser 1 bisIf R “is lower alkyl, this contains 1 to
4 Kohlenstoffatome und stellt bevorzugt Methyl dar.4 carbon atoms and preferably represents methyl.
Der Substituent R bedeutet vorzugsweise Halogen, d.h. Chlor, Brom oder Fluor, und stellt bevorzugt Chlor dar. Falls R Niederalkyl oder Niederalkoxy bedeutet, so enthält dieser vorzugsweise 1 bis 4, z.B. 2 oder insbesondere 1 Kohlenstoffatome. Falls R einen Acyloxy- oder Acylaminorest bedeutet, so enthält dieser vorzugsweise 1 bis 4, insbesondere 2, Kohlenstoffatome. R3 befindet sich vorzugsweise j.n stellung 5.The substituent R preferably denotes halogen, ie chlorine, bromine or fluorine, and preferably represents chlorine. If R denotes lower alkyl or lower alkoxy, this preferably contains 1 to 4, for example 2 or in particular 1, carbon atoms. If R is an acyloxy or acylamino radical, this preferably contains 1 to 4, in particular 2, carbon atoms. R 3 is preferably located j. n position 5.
Die Lactonisierung von Verbindungen der Formel II gemäss dem erfindungsgemässen Verfahren erfolgt nacli an sich bekannten Methoden, z.B. wie in Beispiel 1 beschrieben.The lactonization of compounds of the formula II according to the process according to the invention takes place according to this methods known per se, e.g. as described in Example 1.
Die als Ausgangsprodukte verwendeten Verbindungen der Formel II können nach an sich bekannten Methoden erhalten v/erden. In üblicher Weise leiten sich diese Verbindungen von den entsprechenden Verbindungen der Formel II ab, in denen R_ und R Wasserstoff bedeuten und in denen gegebenenfalls die Hydroxygruppe im Ringgerüst vorübergehend durch eine Alkoxygruppe und die freie Carboxylgruppe vorübergehend durch eine Estergruppe geschützt werden.The compounds of the formula II used as starting materials can be obtained by methods known per se v / earth. In the usual way, these compounds are derived from the corresponding compounds of Formula II, in which R_ and R are hydrogen and in which optionally the hydroxyl group in the ring skeleton is temporarily replaced by an alkoxy group and the free carboxyl group can be temporarily protected by an ester group.
609839/1021609839/1021
- 3 - Case 100-4318- 3 - Case 100-4318
Die Verbindungen der Formel I zeichnen sich durch pharmakologische Effekte aus und können daher als Heilmittel verwendet werden. So besitzen die Verbindungen der Formel I eine ödemhemmende und entzündungshemmende Wirkung. .The compounds of formula I are distinguished by pharmacological effects and can therefore be used as Remedies are used. Thus, the compounds of the formula I have an anti-edema and anti-inflammatory properties Effect. .
Ferner besitzen die Verbindungen der Formel I eine fiebersenkende und analgetische Wirkung. Schliesslich eignen sie sich als Blutplättchen-Aggregations-Hemmer.The compounds of the formula I also have an antipyretic and analgesic effect. In the end they are suitable as platelet aggregation inhibitors.
Als Heilmittel können die Verbindungen der Formel I zusammen mit üblichen pharmazeutischen Hilfsstoffen in galenischen Zubereitungen, wie z.B. Tabletten, Kapseln oder Lösungen, enthalten sein.. Diese galenischen Zubereitungen können nach an sich bekannten Methoden hergestellt werden.The compounds of the formula I can be used as medicaments together with customary pharmaceutical auxiliaries be contained in pharmaceutical preparations such as tablets, capsules or solutions .. These Pharmaceutical preparations can be produced by methods known per se.
In den nachfolgenden Beispielen erfolgen alle Temperaturangaben in Celsiusgraden und sind unkorrigiert.In the following examples, all temperatures are given in degrees Celsius and are uncorrected.
609839/1021609839/1021
Case 100-4318Case 100-4318
COOH IICOOH II
Case 100-4318Case 100-4318
Beispiel 1; 5-ChIQrO-G-cyclohexyl-2 Example 1; 5-ChIQrO-G-cyclohexyl-2 11 3-dihydrobenzofuranon-23-dihydrobenzofuranone-2
5 g 3-Chloro-4-cyclohexyl-6-hydroxy-phenylessigsäure werden unter Erwärmen in Toluol gelöst,, mit 50 mg p-Toluolsulfonsäure versetzt und darauf 3 Stunden am Wasserabscheider gekocht. Das nach Abdampfen zurückbleibende OeI wird an der 100-fachen Menge Kieselgel Merck gereinigt. Mit Chloroform lässt sich das. gewünschte Produkt eluieren und aus Methylenchlorid-Petroläther Umkristallisieren. Die Kristalle schmelzen bei 100 - 102 °.5 g of 3-chloro-4-cyclohexyl-6-hydroxyphenylacetic acid are dissolved in toluene while warming, mixed with 50 mg of p-toluenesulfonic acid and then Boiled for 3 hours on the water separator. The OeI remaining after evaporation becomes 100-fold Lot of silica gel Merck purified. The desired product can be eluted with chloroform and from methylene chloride-petroleum ether Recrystallize. The crystals melt at 100-102 °.
In analoger Weise werden die folgenden Verbindungen der Formel I hergestellt, wobei R1, R_ und R_ folgende Bedeutung haben:The following compounds of the formula I are prepared in an analogous manner, where R 1 , R_ and R_ have the following meanings:
609839/1021609839/1021
Case 100-4318Case 100-4318
R,R,
S chme l.zpunktS chme l. Point
-O-O
CH.CH.
CH,CH,
/CH3 XH/ CH 3 XH
CH,CH,
5-CH.5-CH.
5-Cl5-Cl
5-CH.5-CH.
5-OCH.5-OCH.
5-CH„CONH5-CH "CONH
5-CH3S5-CH 3 S
5-C15-C1
5-ΟΗ5-ΟΗ
5-CH„COO5-CH "COO
157 - 158157-158
88 - 8988-89
77 - 7877-78
amorphamorphous
195 - 196195 - 196
104 - 105104-105
28 - 2928-29
amorphamorphous
amorphamorphous
609839/1 COPY 609839/1 COPY
Claims (6)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH312975A CH614707A5 (en) | 1975-03-12 | 1975-03-12 | Process for the preparation of novel dihydrobenzofuranone derivatives |
| CH967875 | 1975-07-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2608697A1 true DE2608697A1 (en) | 1976-09-23 |
Family
ID=25692258
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762608697 Withdrawn DE2608697A1 (en) | 1975-03-12 | 1976-03-03 | NEW ORGANIC COMPOUNDS, THEIR PRODUCTION AND USE |
Country Status (19)
| Country | Link |
|---|---|
| JP (1) | JPS51113864A (en) |
| AT (1) | AT357516B (en) |
| AU (1) | AU508681B2 (en) |
| CA (1) | CA1086757A (en) |
| DD (1) | DD125210A5 (en) |
| DE (1) | DE2608697A1 (en) |
| DK (1) | DK137274B (en) |
| ES (1) | ES445922A1 (en) |
| FI (1) | FI760548A (en) |
| FR (1) | FR2303540A1 (en) |
| GB (1) | GB1546701A (en) |
| IE (1) | IE43704B1 (en) |
| IL (1) | IL49192A (en) |
| NL (1) | NL7602393A (en) |
| NO (1) | NO760745L (en) |
| NZ (1) | NZ180273A (en) |
| PT (1) | PT64886B (en) |
| SE (1) | SE7603053L (en) |
| YU (1) | YU63576A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4514415A (en) * | 1981-10-28 | 1985-04-30 | Ciba Geigy Corporation | Benzofuran-2(3H)-ones used as anti-inflammatory agents |
| US4849428A (en) * | 1987-11-23 | 1989-07-18 | The Procter & Gamble Company | Cyclic anti-inflammatory derivatives of di-tert-butylphenol compounds, compositions and use |
-
1976
- 1976-03-03 DK DK92176AA patent/DK137274B/en not_active Application Discontinuation
- 1976-03-03 FI FI760548A patent/FI760548A/fi not_active Application Discontinuation
- 1976-03-03 DE DE19762608697 patent/DE2608697A1/en not_active Withdrawn
- 1976-03-04 NO NO760745A patent/NO760745L/no unknown
- 1976-03-05 SE SE7603053A patent/SE7603053L/en unknown
- 1976-03-08 NL NL7602393A patent/NL7602393A/en not_active Application Discontinuation
- 1976-03-09 GB GB9315/76A patent/GB1546701A/en not_active Expired
- 1976-03-10 PT PT64886A patent/PT64886B/en unknown
- 1976-03-10 AT AT173876A patent/AT357516B/en not_active IP Right Cessation
- 1976-03-10 DD DD191782A patent/DD125210A5/xx unknown
- 1976-03-10 ES ES445922A patent/ES445922A1/en not_active Expired
- 1976-03-10 IL IL49192A patent/IL49192A/en unknown
- 1976-03-10 FR FR7606829A patent/FR2303540A1/en active Granted
- 1976-03-10 CA CA247,552A patent/CA1086757A/en not_active Expired
- 1976-03-10 NZ NZ180273A patent/NZ180273A/en unknown
- 1976-03-10 IE IE501/76A patent/IE43704B1/en unknown
- 1976-03-11 YU YU00635/76A patent/YU63576A/en unknown
- 1976-03-11 JP JP51025655A patent/JPS51113864A/en active Pending
- 1976-03-12 AU AU11970/76A patent/AU508681B2/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4514415A (en) * | 1981-10-28 | 1985-04-30 | Ciba Geigy Corporation | Benzofuran-2(3H)-ones used as anti-inflammatory agents |
| US4849428A (en) * | 1987-11-23 | 1989-07-18 | The Procter & Gamble Company | Cyclic anti-inflammatory derivatives of di-tert-butylphenol compounds, compositions and use |
Also Published As
| Publication number | Publication date |
|---|---|
| IE43704L (en) | 1976-09-12 |
| CA1086757A (en) | 1980-09-30 |
| PT64886A (en) | 1976-03-31 |
| NZ180273A (en) | 1978-03-06 |
| FI760548A (en) | 1976-09-13 |
| DK137274B (en) | 1978-02-13 |
| SE7603053L (en) | 1976-09-13 |
| FR2303540B1 (en) | 1979-07-20 |
| ATA173876A (en) | 1979-12-15 |
| PT64886B (en) | 1977-11-17 |
| AT357516B (en) | 1980-07-10 |
| FR2303540A1 (en) | 1976-10-08 |
| AU1197076A (en) | 1977-09-15 |
| JPS51113864A (en) | 1976-10-07 |
| IE43704B1 (en) | 1981-05-06 |
| NL7602393A (en) | 1976-09-14 |
| DD125210A5 (en) | 1977-04-06 |
| YU63576A (en) | 1982-05-31 |
| GB1546701A (en) | 1979-05-31 |
| DK137274C (en) | 1978-07-17 |
| AU508681B2 (en) | 1980-03-27 |
| IL49192A0 (en) | 1976-05-31 |
| IL49192A (en) | 1981-01-30 |
| NO760745L (en) | 1976-09-14 |
| DK92176A (en) | 1976-09-13 |
| ES445922A1 (en) | 1977-08-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8139 | Disposal/non-payment of the annual fee |