NO760745L - - Google Patents
Info
- Publication number
- NO760745L NO760745L NO760745A NO760745A NO760745L NO 760745 L NO760745 L NO 760745L NO 760745 A NO760745 A NO 760745A NO 760745 A NO760745 A NO 760745A NO 760745 L NO760745 L NO 760745L
- Authority
- NO
- Norway
- Prior art keywords
- formula
- compounds
- carbon atoms
- stands
- stated
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 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
- 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
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000004519 manufacturing process Methods 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
- 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
- 206010037660 Pyrexia Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 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
- 229940127218 antiplatelet drug Drugs 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
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=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
- 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
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 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
- 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
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000000106 platelet aggregation inhibitor Substances 0.000 description 1
- 230000001603 reducing effect Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 125000001424 substituent group Chemical group 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
"Fremgangsmåte for fremstilling av nye "Procedure for the production of new
organiske_f orbindelser_." organic_compounds_."
Foreliggende oppfinnelse vedrører en fremgangsmåte for fremstilling av nye organiske forbindelser med formel I The present invention relates to a method for the production of new organic compounds with formula I
hvori R1står for alkyl med 1 til 10 karbonatomer, cykloalkyl med 3 til 8 karbonatomer eller fenyl, R2står for hydrogen eller lavere alkyl og står for halogen, nitro, lavere alkyl, metyltio, hydroksy, lavere alkoksy, acyloksy eller acylamino, idet R^ikke betyr hydrogen når R^ befinner seg i 5-still ingen, og når R^og R2 står for en rettlinjet alkylkjede med 1 til 5 karbonatomer og er idenfeiskå. Det særegne ved fremgangsmåten i henhold til oppfinnelsen er at forbindelser med formel II in which R1 represents alkyl of 1 to 10 carbon atoms, cycloalkyl of 3 to 8 carbon atoms or phenyl, R2 represents hydrogen or lower alkyl and represents halogen, nitro, lower alkyl, methylthio, hydroxy, lower alkoxy, acyloxy or acylamino, R^ not means hydrogen when R^ is in the 5-still none, and when R^ and R 2 stand for a linear alkyl chain with 1 to 5 carbon atoms and are idenfeiskå. The peculiarity of the method according to the invention is that compounds of formula II
hvori R^, R^ og R^har den ovennevnte betydning, laktoniseres. in which R^, R^ and R^ have the above meaning, are lactonized.
Hvis R. betyr cykloalkyl inneholder denne rest foretrukket 5 til 7 karbonatomer og utgjør spesielt cyklopentyl eller cykloheksyl. Hvis R^ betyr alkyl, så inneholder denne foretrukket 3 til 6, spesielt 3 eller 4,>.karbonatomer og er foretrukket forgrenet og utgjør spesielt isobutyl eller isopropyl. If R. means cycloalkyl, this residue preferably contains 5 to 7 carbon atoms and constitutes in particular cyclopentyl or cyclohexyl. If R 1 means alkyl, then this preferably contains 3 to 6, especially 3 or 4, carbon atoms and is preferably branched and constitutes in particular isobutyl or isopropyl.
Betyr R^lavere alkyl inneholder denne 1 til 4 karbonatomer og utgjør foretrukket metyl. Means R^lower alkyl, this contains 1 to 4 carbon atoms and is preferably methyl.
Substituenten R^betyr foretrukket halogen, dvs. klor, brom eller fluor, og utgjør foretrukket klor. Hvis R^ betyr lavere alkyl eller ibavere alkoksy, inneholder denne foretrukket 1 til 4, f.eks. 2 eller spesielt 1 karbonatom© Hvis R^betyr en acyloksy eller aeyiaminorest, inneholder denne foretrukket 1 til 4, spesielt 2 karbonatomer. Rj. befinner seg foretrukket i 5-stillingen. The substituent R^ preferably means halogen, i.e. chlorine, bromine or fluorine, and preferably constitutes chlorine. If R 1 means lower alkyl or lower alkoxy, this preferably contains 1 to 4, e.g. 2 or in particular 1 carbon atom© If R^ denotes an acyloxy or aeyiamino radical, this preferably contains 1 to 4, in particular 2 carbon atoms. Rj. is preferably located in the 5 position.
Laktoniseringen av forbindelsene med formel II ved fremgangsmåtenThe lactonization of the compounds of formula II by the process
i henhold til oppfinnelsen skjer etter i og for seg kjente metoder, f.eks. som beskrevet i eksempel I. according to the invention takes place according to per se known methods, e.g. as described in Example I.
De som utgangsprodukter anvendte forbindelser med formel II kan erholdes etter i og for seg kjente metoder. På vanlig måte av-leder disse forbindelser seg fra de tilsvarende forbindelser med formel II, hvori R^og R^betyr hydrogen og hvori eventuelt hydroksygruppen i ringskjellettet midlertidig beskyttes med en alkoksygruppe og den fri karboksylgruppe midlertidig med en ester-gruppe. The compounds of formula II used as starting products can be obtained by methods known per se. In the usual way, these compounds are derived from the corresponding compounds of formula II, in which R^ and R^ mean hydrogen and in which, where appropriate, the hydroxy group in the ring skeleton is temporarily protected with an alkoxy group and the free carboxyl group temporarily with an ester group.
Forbindelsene med formel I utmerker seg ved farmakologiske virkninger og kan følgelig anvendes som medisin. Således har forbindelsene med formel I en ødemhemmende og betennelseshemmende virkning. The compounds of formula I are distinguished by their pharmacological effects and can consequently be used as medicine. Thus, the compounds of formula I have an anti-oedema and anti-inflammatory effect.
Videre har forbindelsene med formel I en febersenkende og anal-getisk virkning. Endelig egner de seg som blodplate-aggregasjohs-s hemmere. Furthermore, the compounds of formula I have a fever-reducing and analgesic effect. Finally, they are suitable as platelet aggregation inhibitors.
Som medisin kan forbindelsene med formel I inneholdes sammen med vanlige farmasøytiske hjelpestoffer i medisinske pneparater som f.eks. tabletter, kapsler eller løsninger. Disse medisinske preparater kan fremstilles etter i og for seg kjente metoder. As medicine, the compounds of formula I can be contained together with common pharmaceutical excipients in medical pneparats such as e.g. tablets, capsules or solutions. These medical preparations can be prepared according to methods known per se.
I de etterfølgende eksempler er alle temperaturangivelser i grader celsius og er ukorrigert. In the following examples, all temperature indications are in degrees Celsius and are uncorrected.
Eksempel 1; 5-kloro-6-cykloheksyl-2^Example 1; 5-Chloro-6-cyclohexyl-2^
5 g '3-kloro-4-cykloheksyl-6-hydroksy-feiryleddiksyre løses under oppvarming i toluea, tilsettes 50 mg p-toluensulfonsyre og kokes deretter i 3 timer under vannutskyllér. Den etter avdamping tilbakeblivende olje renses på den 100-dobbelte mengde kiselgel "Merk". Med kloroform lar det ønskede produkt seg eluere og omkrystalliseres fra metylenklorid-petroleter. Krystallene smelter ved 100 - 102°C. 5 g of 3-chloro-4-cyclohexyl-6-hydroxyfeyrylacetic acid are dissolved while heating in toluene, 50 mg of p-toluenesulfonic acid are added and then boiled for 3 hours under a water rinse. The oil remaining after evaporation is purified on the 100-fold amount of silica gel "Mark". With chloroform, the desired product can be eluted and recrystallized from methylene chloride-petroleum ether. The crystals melt at 100 - 102°C.
På analog måte fremstilles de følgende forbindelser med formel I, idet R^, R^ og R^har følgende betydning: In an analogous way, the following compounds of formula I are prepared, where R^, R^ and R^ have the following meanings:
Claims (4)
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 |
---|---|
NO760745L true NO760745L (en) | 1976-09-14 |
Family
ID=25692258
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO760745A NO760745L (en) | 1975-03-12 | 1976-03-04 |
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) |
Families Citing this family (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 FI FI760548A patent/FI760548A/fi not_active Application Discontinuation
- 1976-03-03 DK DK92176AA patent/DK137274B/en 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 AT AT173876A patent/AT357516B/en not_active IP Right Cessation
- 1976-03-10 IE IE501/76A patent/IE43704B1/en unknown
- 1976-03-10 PT PT64886A patent/PT64886B/en unknown
- 1976-03-10 CA CA247,552A patent/CA1086757A/en not_active Expired
- 1976-03-10 NZ NZ180273A patent/NZ180273A/en unknown
- 1976-03-10 FR FR7606829A patent/FR2303540A1/en active Granted
- 1976-03-10 IL IL49192A patent/IL49192A/en unknown
- 1976-03-10 ES ES445922A patent/ES445922A1/en not_active Expired
- 1976-03-10 DD DD191782A patent/DD125210A5/xx 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
Also Published As
Publication number | Publication date |
---|---|
SE7603053L (en) | 1976-09-13 |
FI760548A (en) | 1976-09-13 |
DK137274C (en) | 1978-07-17 |
ATA173876A (en) | 1979-12-15 |
NZ180273A (en) | 1978-03-06 |
DD125210A5 (en) | 1977-04-06 |
FR2303540B1 (en) | 1979-07-20 |
AT357516B (en) | 1980-07-10 |
GB1546701A (en) | 1979-05-31 |
DE2608697A1 (en) | 1976-09-23 |
AU1197076A (en) | 1977-09-15 |
CA1086757A (en) | 1980-09-30 |
PT64886A (en) | 1976-03-31 |
IE43704B1 (en) | 1981-05-06 |
IE43704L (en) | 1976-09-12 |
DK137274B (en) | 1978-02-13 |
IL49192A (en) | 1981-01-30 |
FR2303540A1 (en) | 1976-10-08 |
JPS51113864A (en) | 1976-10-07 |
YU63576A (en) | 1982-05-31 |
IL49192A0 (en) | 1976-05-31 |
AU508681B2 (en) | 1980-03-27 |
NL7602393A (en) | 1976-09-14 |
DK92176A (en) | 1976-09-13 |
ES445922A1 (en) | 1977-08-16 |
PT64886B (en) | 1977-11-17 |
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