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- Withdrawn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
- 238000004519 manufacturing process Methods 0.000 title description 2
- 150000002894 organic compounds Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 125000004423 acyloxy group Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000004442 acylamino group Chemical group 0.000 claims description 2
- -1 methylthio, hydroxy Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 229940126601 medicinal product Drugs 0.000 claims 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- MHPYDQXOJSSKDU-UHFFFAOYSA-N 2-(5-chloro-4-cyclohexyl-2-hydroxyphenyl)acetic acid Chemical compound C1=C(O)C(CC(=O)O)=CC(Cl)=C1C1CCCCC1 MHPYDQXOJSSKDU-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 230000003501 anti-edematous effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000001754 anti-pyretic effect Effects 0.000 description 1
- 229940127218 antiplatelet drug Drugs 0.000 description 1
- 239000002221 antipyretic Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000007273 lactonization reaction Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000000106 platelet aggregation inhibitor Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Furan Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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) | FI760548A7 (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 DE DE19762608697 patent/DE2608697A1/en not_active Withdrawn
- 1976-03-03 DK DK92176AA patent/DK137274B/en not_active Application Discontinuation
- 1976-03-03 FI FI760548A patent/FI760548A7/fi not_active Application Discontinuation
- 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 ES ES445922A patent/ES445922A1/en not_active Expired
- 1976-03-10 FR FR7606829A patent/FR2303540A1/en active Granted
- 1976-03-10 DD DD191782A patent/DD125210A5/xx unknown
- 1976-03-10 IL IL49192A patent/IL49192A/en unknown
- 1976-03-10 AT AT173876A patent/AT357516B/en not_active IP Right Cessation
- 1976-03-10 NZ NZ180273A patent/NZ180273A/en unknown
- 1976-03-10 CA CA247,552A patent/CA1086757A/en not_active Expired
- 1976-03-10 IE IE501/76A patent/IE43704B1/en unknown
- 1976-03-10 PT PT64886A patent/PT64886B/en unknown
- 1976-03-11 JP JP51025655A patent/JPS51113864A/en active Pending
- 1976-03-11 YU YU00635/76A patent/YU63576A/en unknown
- 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 |
| ATA173876A (en) | 1979-12-15 |
| JPS51113864A (en) | 1976-10-07 |
| IL49192A0 (en) | 1976-05-31 |
| NO760745L (en) | 1976-09-14 |
| FI760548A7 (en) | 1976-09-13 |
| GB1546701A (en) | 1979-05-31 |
| DK92176A (en) | 1976-09-13 |
| ES445922A1 (en) | 1977-08-16 |
| DK137274B (en) | 1978-02-13 |
| AU1197076A (en) | 1977-09-15 |
| PT64886B (en) | 1977-11-17 |
| AU508681B2 (en) | 1980-03-27 |
| NZ180273A (en) | 1978-03-06 |
| PT64886A (en) | 1976-03-31 |
| DD125210A5 (en) | 1977-04-06 |
| DK137274C (en) | 1978-07-17 |
| FR2303540A1 (en) | 1976-10-08 |
| AT357516B (en) | 1980-07-10 |
| NL7602393A (en) | 1976-09-14 |
| YU63576A (en) | 1982-05-31 |
| SE7603053L (en) | 1976-09-13 |
| IL49192A (en) | 1981-01-30 |
| CA1086757A (en) | 1980-09-30 |
| FR2303540B1 (en) | 1979-07-20 |
| IE43704B1 (en) | 1981-05-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8139 | Disposal/non-payment of the annual fee |