NO751455L - - Google Patents
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- Publication number
- NO751455L NO751455L NO751455A NO751455A NO751455L NO 751455 L NO751455 L NO 751455L NO 751455 A NO751455 A NO 751455A NO 751455 A NO751455 A NO 751455A NO 751455 L NO751455 L NO 751455L
- Authority
- NO
- Norway
- Prior art keywords
- formula
- compounds
- stands
- substituents
- meaning
- Prior art date
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- 150000001875 compounds Chemical class 0.000 claims description 30
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
- 239000012298 atmosphere Substances 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000011261 inert gas Substances 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 125000000815 N-oxide group Chemical group 0.000 claims description 3
- SJDFGMAJLVKODV-UHFFFAOYSA-N 5,5,7,7-tetramethylfuro[3,4-e][1,2,4]triazine Chemical class N1=CN=C2C(C)(C)OC(C)(C)C2=N1 SJDFGMAJLVKODV-UHFFFAOYSA-N 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- 239000000203 mixture Substances 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 230000001624 sedative effect Effects 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- -1 benzene or toluene Chemical class 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000000932 sedative agent Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- RXJWBJGNIOZICN-UHFFFAOYSA-N 5,5,7,7-tetramethyl-3-(3-nitrophenyl)-4-oxidofuro[3,4-e][1,2,4]triazin-4-ium Chemical compound CC1(C)OC(C)(C)C([N+]=2[O-])=C1N=NC=2C1=CC=CC([N+]([O-])=O)=C1 RXJWBJGNIOZICN-UHFFFAOYSA-N 0.000 description 2
- BBQNHTWKPXQENB-UHFFFAOYSA-N 5,5,7,7-tetramethyl-4-oxido-3-phenylfuro[3,4-e][1,2,4]triazin-4-ium Chemical compound CC1(C)OC(C)(C)C([N+]=2[O-])=C1N=NC=2C1=CC=CC=C1 BBQNHTWKPXQENB-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 2
- 238000006396 nitration reaction Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229910000510 noble metal Inorganic materials 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 2
- OJVFWXSWSBEQRL-UHFFFAOYSA-N 5,5,7,7-tetramethyl-3-phenylfuro[3,4-e][1,2,4]triazine Chemical compound N=1N=C2C(C)(C)OC(C)(C)C2=NC=1C1=CC=CC=C1 OJVFWXSWSBEQRL-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
- VRDJHWPWOGKRMU-UHFFFAOYSA-N N-(4-hydrazinylidene-2,2,5,5-tetramethyloxolan-3-ylidene)hydroxylamine Chemical compound CC1(C)OC(C)(C)C(=NO)C1=NN VRDJHWPWOGKRMU-UHFFFAOYSA-N 0.000 description 1
- 241000906446 Theraps Species 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001559 benzoic acids Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 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
- 239000000969 carrier Substances 0.000 description 1
- FGGUAEKPLDMWSF-HMHFYOQSSA-N chembl2376821 Chemical compound O([C@@H]1[C@@H]2[C@@H]3O[C@]3(CO)[C@@H](O)[C@@]3(O)[C@H]([C@]2([C@H](C)C[C@@]1(O1)C(C)=C)O2)C[C@@H]([C@@H]3O)C)C21C1=CC=CC=C1 FGGUAEKPLDMWSF-HMHFYOQSSA-N 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- 239000008241 heterogeneous mixture Substances 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
- 230000000147 hypnotic effect Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 150000002689 maleic acids Chemical class 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 230000000802 nitrating effect Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003444 succinic acids Chemical class 0.000 description 1
- BQFPCTXLBRVFJL-UHFFFAOYSA-N triethoxymethylbenzene Chemical compound CCOC(OCC)(OCC)C1=CC=CC=C1 BQFPCTXLBRVFJL-UHFFFAOYSA-N 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- XPDWGBQVDMORPB-UHFFFAOYSA-N trifluoromethane acid Natural products FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
Foreliggende oppfinnelse vedrorer en fremgangsmåte for fremstilling av nye 5,5,7,7-tetrametylfuro(3,4-e)as-triaziner med formel I The present invention relates to a process for the production of new 5,5,7,7-tetramethylfuro(3,4-e)as-triazines of formula I
hvori X står for og og R 2 er like eller forskjellige og betyr i det enkelte tilfelle hydrogen, fluor, klor, en alkylgruppe med 1-4 karbonatomer, en rettkjedet alkoksygruppe med 1-4 karbonatomer, amino, nitro eller trifluormetyl, med den betingelse at (I) hvis en av substituentene og R£betyr nitro har den annen av disse substituenter en annen betydning enn nitro eller trifluormetyl, (II) hvis en av substituentene R^og R2står for t-butyl eller trifluormetyl, står den annen av disse substituenter, hvis den befinner seg på det nabostående karbonatom, ikke for trifluormetyl eller t-butyl, og (III) hvis en av substituentene R, og R_ står for t-butyl, står den annen av disse substituenter, hvis den befinner seg. på det nabostående karbonatom, ikke for nitro. in which X stands for and and R 2 are the same or different and mean in each case hydrogen, fluorine, chlorine, an alkyl group with 1-4 carbon atoms, a straight-chain alkoxy group with 1-4 carbon atoms, amino, nitro or trifluoromethyl, with the condition that (I) if one of the substituents and R£ means nitro, the other of these substituents has a different meaning than nitro or trifluoromethyl, (II) if one of the substituents R^ and R2 stands for t-butyl or trifluoromethyl, the other of these substituents, if it is on the neighboring carbon atom, not for trifluoromethyl or t-butyl, and (III) if one of the substituents R, and R_ stands for t-butyl, the other of these substituents, if present. on the neighboring carbon atom, not for nitro.
Forbindelsene med formel I kan overfores i sine syreaddisjonssalter og omvendt. The compounds of formula I can be transferred in their acid addition salts and vice versa.
Det særegne ved fremgangsmåten er atThe peculiarity of the procedure is that
a) for fremstilling av forbindelser med formel Ia,a) for the preparation of compounds of formula Ia,
hvori R^ og R£ har den ovennevnte betydning, omsettes en in which R^ and R£ have the above-mentioned meaning, a is converted
forbindelse med formel IIcompound of formula II
i en inert gassatmosfære med forbindelser med formel III hvori R^ og R£ har den ovennevnte betydning og R^står for metyl eller etyl, éiler b) for fremstilling av forbindelser med formel Iaa hvori R1' står for hydrogen, fluor, k&or, en alkylgruppe med 1-4 karbonatomer, eller en rettkjedet alkoksygruppe med 1-4 karbonatomer eller står for amino, med den betingelse at ' har en annen betydning enn t-butyl, hvis den befinner seg på det karbonatom som er nabostående til nitrogruppen, ved at forbindelser med formellab in an inert gas atmosphere with compounds of formula III in which R^ and R£ have the above meaning and R^ stands for methyl or ethyl, éiler b) for the preparation of compounds of formula Iaa in which R1' stands for hydrogen, fluorine, carbon, a alkyl group with 1-4 carbon atoms, or a straight-chain alkoxy group with 1-4 carbon atoms or stands for amino, with the proviso that ' has a different meaning than t-butyl, if it is located on the carbon atom adjacent to the nitro group, in that compounds with formula lab
hvori R^1 har den ovennevnte betydning, nitreres eller wherein R^1 has the above meaning, is nitrated or
c) forbindelse med formel Ib,c) compound of formula Ib,
hvori R^og R£har den ovennevnte betydning, fremstilles ved at in which R^ and R£ have the above meaning, is produced by at
N-oksydgruppen i forbindelsene med formel Ia reduseres i inert-gassatmo.sfære. The N-oxide group in the compounds of formula Ia is reduced in an inert gas atmosphere.
Den under a) angitte fremgangsmåte kan gjennomfbres søm beskrevet i det fblgende: Omsetningen av forbindelsene med formel II med forbindelsene med formel III kan hensiktsmessig gjennomfbres ved temperaturerspå 70 til 200°C, foretrukket 130 til 150°C, idet reaksjonstidene f.eks. kan utgjore 12 til 36 timer, spesielt 15 til 20 timer. Omsetningen skjer hensiktsmessig i et inert organisk løsnings-middel, f.eks. aromatiske hydrokarboner som benzen eller toluen, og lavere alkanoler som metanol eller etanol. I stedet for inerte organiske løsningsmidler kan likeledes et overskudd av forbindelsene med formel III velges som reaksjonsmedium. Den inérte gassatmosfære består f.eks. av helium, argon eller foretrukket nitrogen. The method indicated under a) can be carried out as described in the following: The reaction of the compounds of formula II with the compounds of formula III can conveniently be carried out at temperatures of 70 to 200°C, preferably 130 to 150°C, the reaction times e.g. can amount to 12 to 36 hours, especially 15 to 20 hours. The reaction conveniently takes place in an inert organic solvent, e.g. aromatic hydrocarbons such as benzene or toluene, and lower alkanols such as methanol or ethanol. Instead of inert organic solvents, an excess of the compounds of formula III can likewise be chosen as reaction medium. The inert gas atmosphere consists of e.g. of helium, argon or preferably nitrogen.
Den under b) angitte fremgangsmåte kan gjennomfbres som beskrevet i det fblgende: Nitreringen av forbindelsene med formel lab skjer på i og for seg kjent måte under anvendelse av vanlige nitronium-ioner dannende reagenser, f.eks. en blanding av svovelsyre og salpetersyre, The method indicated under b) can be carried out as described in the following: The nitration of the compounds of formula lab takes place in a manner known per se using common reagents forming nitronium ions, e.g. a mixture of sulfuric acid and nitric acid,
en blanding av trifluormetansulfonsyre og rykende salpetersyre, eller en blanding av hydrogenfluorid og .dinitrogenperoksyd i nitrometan (ved -20°C). Det foretrukne nitreringsmiddel er imidlertid en blanding av trifluormetansyre og rykende salpetersyre, foretrukket i et molforhold på 2:1. Nitreringen skjer hensiktsmessig i et inert organisk'løsningsmiddel. Egnede løsningsmidler er aromatiske hydrokarboner som metylenklorid eller kloroform, foretrukket metylenklorid. a mixture of trifluoromethanesulfonic acid and fuming nitric acid, or a mixture of hydrogen fluoride and dinitrogen peroxide in nitromethane (at -20°C). However, the preferred nitrating agent is a mixture of trifluoromethane acid and fuming nitric acid, preferably in a molar ratio of 2:1. The nitration conveniently takes place in an inert organic solvent. Suitable solvents are aromatic hydrocarbons such as methylene chloride or chloroform, preferably methylene chloride.
ReaksjoiSbemperaturen utgjor hensiktsmessig fra -80 til +70°C, foretrukket fra -35 til +35°C og reaksjonstiden kan f.eks. utgjore fra 19 til 76 timer, spesielt fra 60 til 75 timer. The reaction temperature is suitably from -80 to +70°C, preferably from -35 to +35°C and the reaction time can e.g. perform from 19 to 76 hours, especially from 60 to 75 hours.
Den under c) angitte fremgangsmåte kan gjennomfbres som beskrevet i det fblgende: The procedure specified under c) can be carried out as described in the following:
Reduksjonen av N-oksydgruppen i forbindelsene med formel Ia kan f.eks. skje under anvendelse av forbindelser med formel IV The reduction of the N-oxide group in the compounds of formula Ia can e.g. take place using compounds of formula IV
hvori Z står for klor, brom eller en alkoksygruppe med it-4 karbonatomer. For denne reaksjon egnede løsningsmidler er f.eks. aromatiske hydrokarboner som benzen eller toluen, eller foretrukket et overskudd av forbindelser med formel IV. in which Z stands for chlorine, bromine or an alkoxy group with it-4 carbon atoms. Solvents suitable for this reaction are e.g. aromatic hydrocarbons such as benzene or toluene, or preferably an excess of compounds of formula IV.
Egnede reaksjonstemperaturer utgjor fra 100 til 210°C/foretrukket fra 140 til 180°C, og reaksjonstiden kan f.eks. utgjore fra 12 til 36 timer, spesielt fra 15 til 20 timer. I stedet for.de ovennevnte forbindelser med formel IV anvender man i fremgangsmåten c) foretrukket syklohexen i nærvær av en katalysator, spesielt en edelmetallkatalysator, som platina, rhodium eller foretrukket palladium, idet disse edelmetaller enten anvendes rene eller på en bærer, f .eks. en bærer av kull, og et av de ovennevnte løsningsmidler. Omsetningen skjer hensiktsmessig ved temperaturer fra 20 til 200°C, foretrukket fra 70 til 110°C, og reaksjonstiden kan f.eks. utgjore fra 5 til 72 timer, spesielt 15 til 30 timer. Egnede ^Løsningsmidler er lavere alkanoler som Suitable reaction temperatures are from 100 to 210°C/preferably from 140 to 180°C, and the reaction time can e.g. perform from 12 to 36 hours, especially from 15 to 20 hours. Instead of the above-mentioned compounds of formula IV, cyclohexene is preferably used in method c) in the presence of a catalyst, especially a noble metal catalyst, such as platinum, rhodium or preferably palladium, these noble metals being either used pure or on a carrier, e.g. . a carrier of carbon, and one of the above-mentioned solvents. The reaction conveniently takes place at temperatures from 20 to 200°C, preferably from 70 to 110°C, and the reaction time can e.g. make from 5 to 72 hours, especially 15 to 30 hours. Suitable ^Solvents are lower alkanols which
metanol eller etanol, foretrukket den sistnevnte. Den i dénne methanol or ethanol, preferably the latter. The one in this one
fremgangsmåtenanvendte inertgassatmosfære er f.eks. én helium-, process-used inert gas atmosphere is e.g. one helium-,
argon- eller foretrukket nitrogen-atmosfære.argon or preferably nitrogen atmosphere.
De véd de ovennevnte fremgangsmåter erholdte forbindelser med formel I kan isoleres og renses på i og for seg kjent måte. The compounds of formula I obtained by the above-mentioned methods can be isolated and purified in a manner known per se.
Forbindelsene med formel I utmerker seg iwred en overordentlig gunstig farmakodynamisk virkning. Spesielt har forbindelsene med formel I en sdvnutlosende og en lett beroligende virkning, påvist f.eks. med resultater av prover som ble beskrevet av Winter i J. Pharm, and Exp. Therap. 94, 7-11 (1948), av S. Irwin (Gordon Research Conference, Medicinal Chemistry, 1959) av Chen (Symposium on Sedative and Hypnotic drugs, Williams and Wilkins, 1954) av Reed-Muench (American Journal of Hygiene 27, 493-497, (1938)) og av I. Geiler, (Psychopharmacologia, I, 42-492 (1960)). The compounds of formula I are distinguished by an extremely favorable pharmacodynamic effect. In particular, the compounds of formula I have a sedative and mild sedative effect, demonstrated e.g. with results of tests described by Winter in J. Pharm, and Exp. Therap. 94, 7-11 (1948), by S. Irwin (Gordon Research Conference, Medicinal Chemistry, 1959) by Chen (Symposium on Sedative and Hypnotic drugs, Williams and Wilkins, 1954) by Reed-Muench (American Journal of Hygiene 27, 493-497, (1938)) and by I. Geiler, (Psychopharmacologia, I, 42-492 (1960)).
Forbindelsene med formel I kan derfor anvendes for innsovning og som svakt beroligende middel. Den for sbvninnledningen tilforte dose skal utgjore fra 35 til 750 mg som hensiktsmessig tilfores i en porsjon ved sengetid. For anvendelse som svakt beroligende mitddel skal forbindelsene med formel I tilfores i en daglig dose på 75 til 1000 mg, hensiktsmessig i mindre doser fra 18 til 500 mg 2 til 4 ganger daglig eller i retardform. The compounds of formula I can therefore be used to induce sleep and as a mild sedative. The dose given for the sbv introduction should be from 35 to 750 mg, which is suitably given in one portion at bedtime. For use as a mild sedative, the compounds of formula I must be administered in a daily dose of 75 to 1000 mg, suitably in smaller doses from 18 to 500 mg 2 to 4 times a day or in retarded form.
Forbindelsene med formel I blandes hensiktsmessig sammen med vanlige.farmasoytisk- tålbare fortynningsmidler eller bærestoffer og eventuelt også.andre tilsetninger og tilfores i form av The compounds of formula I are suitably mixed together with usual pharmaceutical-tolerable diluents or carriers and possibly also other additives and supplied in the form of
tabletter eller kapsler.tablets or capsules.
Forbindelsene med formel I kan tilfores i form av de fri baser eller i form av déres f armasbytask; .tålbare syreaddisjonssalter, The compounds of formula I can be supplied in the form of the free bases or in the form of their framsbytask; .tolerable acid addition salts,
idet virkningen av saltene er av den samme stbrrelsesordnenas the effect of the salts is of the same principle
som virkningen av basene^ For saltdannelse egnede syrer er spesielt mineralsyrer:som saltsyre, brom, hydrogensyre og svovelsyre, og organiske syreæ som.ravsyre, benzosyre og maleinsyre. as the action of the bases^ Acids suitable for salt formation are especially mineral acids: such as hydrochloric, bromic, hydrogen and sulfuric acids, and organic acids such as succinic, benzoic and maleic acids.
De foretrukne forbindelser med formel I er dem hvori betyr en nitrogruppe i meta-stlling og spesielt dem hvori R står for hydrogen. The preferred compounds of formula I are those in which a nitro group is in the meta position and especially those in which R stands for hydrogen.
Eksempel 1: 5, 7- dihydro- 5, 5, 7, 7- tetrametyl- 3- fenyl- furo Example 1: 5,7-dihydro-5,5,7,7-tetramethyl-3-phenyl-furo
( 3, 4- e)- as- triazin- 4- oksyd.( 3, 4-e)- as- triazine- 4- oxide.
En blanding av 6,84 g 2,2-5,5-tetrame£yl-3,4(2H,5H)-furandion-3-hydrazon~4-oxim og 15 ml trietylortobenzoat oppvarmes i- ' nitrogenatmosfære i 18 timer til koking ved en badtemperatur på 140°C. Beretter oppvarmes dsn erholdte lbsning videre i 8 timer ved en badtemperatur. hvor de flyktige bestanddeler av-destilleres. Den tilbakeblivende blanding avkjbles til 25°C A mixture of 6.84 g of 2,2-5,5-tetramethyl-3,4(2H,5H)-furandione-3-hydrazone-4-oxime and 15 ml of triethyl orthobenzoate is heated in a nitrogen atmosphere for 18 hours to boiling at a bath temperature of 140°C. The solution obtained is further heated for 8 hours at a bath temperature. where the volatile components are distilled off. The remaining mixture is cooled to 25°C
og tilsettes £00 ml eter. Det dannede bunnfall frafiltteres og filtratet inndampes til tbrrhet i vakuum ved 100°C. Den erholdte rest loses i eter og gjennomllbsningen ledes hydrogen- - kloridgass til metning. Helved utfelles 5,7-dihydro-5,5,7,7- and £00 ml of ether is added. The precipitate formed is filtered off and the filtrate is evaporated to dryness in vacuum at 100°C. The residue obtained is dissolved in ether and hydrogen chloride gas is passed through the solution until saturation. Hell precipitates 5,7-dihydro-5,5,7,7-
tetrametyl-3-fenylfuro(3,4-e)as-triazih-4-oksyd i form av sitt hydroklorid med smeltepunkt 154-156°C. tetramethyl-3-phenylfuro(3,4-e)as-triazih-4-oxide in the form of its hydrochloride with a melting point of 154-156°C.
Eksempel 2: 5, 7- dihydro- 5, 5, 7, 7- tetrametyl- 3-( m- nitrofenyl) Example 2: 5,7-dihydro-5,5,7,7-tetramethyl-3-(m-nitrophenyl)
furo( 3, 4- e)- as- triazin- 4- oksyd.furo(3,4-e)-as-triazine-4-oxide.
En blanding av 6,84 g 2,2,5,5-tetrametyl-3,4(2H,5H)-furandion-3-hydrazon-4-oxim og 16,14 g iri-nitrotrietyl-ortobenzoat oppvarmes under nitrogen i 24 timer ved den badtemperatur på 140°C. Deretter avkjoles blandingen til 25°C og tilsettes 250 ml eter. Det dainaae bunnfalr f raf ilticeres og filtratet inndampes i vakuum ved 100°C. Resten omkrystalliseres fra metylenklorid/hexan hvorved 5,7-dihydro-5,5,7,7-tetrametyl-3-(m-nitrofenyl)furo (3,4-e)-as-triazin-4-oksyd med smeltepunkt 202-204°C erholdes. A mixture of 6.84 g of 2,2,5,5-tetramethyl-3,4(2H,5H)-furandione-3-hydrazone-4-oxime and 16.14 g of iri-nitrotriethyl orthobenzoate is heated under nitrogen for 24 hours at the bath temperature of 140°C. The mixture is then cooled to 25°C and 250 ml of ether is added. The resulting precipitate is filtered off and the filtrate is evaporated in vacuo at 100°C. The residue is recrystallized from methylene chloride/hexane whereby 5,7-dihydro-5,5,7,7-tetramethyl-3-(m-nitrophenyl)furo (3,4-e)-as-triazine-4-oxide with melting point 202- 204°C is obtained.
Eksempel 3: 5, 7- dihydro- 5, 5, 7, 7- tetrametyl- 3-( m- nitrofenyl) Example 3: 5,7-dihydro-5,5,7,7-tetramethyl-3-(m-nitrophenyl)
furo( 3, 4- e)- as- triazin- 4- oksyd.furo(3,4-e)-as-triazine-4-oxide.
En blanding av 0,2 ml rykende salpetersyre og 1,5 g trifluormetansulfonsyre i 15'ml vannfritt metylenklorid omrbres i 1 A mixture of 0.2 ml of fuming nitric acid and 1.5 g of trifluoromethanesulfonic acid in 15 ml of anhydrous methylene chloride is stirred in 1
time ved 25°C og innfores deretter dråpevis i en lbsning av 0,542 g 5,7-dihydro-5,5,7,7atetrametyl-3-fenylfuro(3,4-e)-as triazin-4-oksyd i 15 ml vannfritt metylenklorid ved -30°C. hour at 25°C and then introduced dropwise into a solution of 0.542 g of 5,7-dihydro-5,5,7,7atetramethyl-3-phenylfuro(3,4-e)-as triazine-4-oxide in 15 ml anhydrous methylene chloride at -30°C.
Den erholdte heterogene blafiding omrbres véd 25°G, % 72 'timer, utrystes deretter på is og nøytraliseres med fast natriumbi-karbonat. Det organiske skikt fjernes og det vandige skikt ekstraheres flere ganger med metylenklorid. De forenede "• organiske skikt vaskes med mettet vandig natriumkloridlbsning, tbrres over magnesiumsulfat og inndampes deretter. Herved erholdes eh hvit rest som omkrystalliseres fra metylenklorid/ hexan. Det erholdte 5,7-dihydro-5,5,7,7-tetrametyl-3-(m-nitrofenyl)-furo(3,4-e)-as-triazin-4-oksyd smelter ved 202-204°C. The obtained heterogeneous mixture is heated at 25°C for 72 hours, then shaken on ice and neutralized with solid sodium bicarbonate. The organic layer is removed and the aqueous layer is extracted several times with methylene chloride. The combined "• organic layers are washed with saturated aqueous sodium chloride solution, passed over magnesium sulfate and then evaporated. This gives a white residue which is recrystallized from methylene chloride/hexane. 5,7-dihydro-5,5,7,7-tetramethyl-3 -(m-nitrophenyl)-furo(3,4-e)-as-triazine-4-oxide melts at 202-204°C.
Eksempel 4; 5, 7- dihydro- 5, 5, 7 , 7- tetrametyl- 3- fenyl- fuco( 3, 4- e)-as- triazin. Example 4; 5, 7- dihydro- 5, 5, 7 , 7- tetramethyl- 3- phenyl- fuco( 3, 4-e)-astriazine.
En blanding av 5,42 g 5,7-dihydro-5,5,7,7-tetrameyl-3-fenylfuro (3, 4-e)-as-trjazin-4-oksyd og 70 ml trietyibf osf it oppvarmes i nitrogenatmosfære i 18 timer til koking ved en badtemperatur A mixture of 5.42 g of 5,7-dihydro-5,5,7,7-tetramethyl-3-phenylfuro (3, 4-e)-as-triazine-4-oxide and 70 ml of triethyl phosphate is heated in a nitrogen atmosphere for 18 hours until boiling at a bath temperature
på 180°C. Deretter fjernes losningsmidlet i vakuum og resten omkrystallieeres fra vandig etanol. Det erholdte 5,7-dihydro-5, 5, 7, 7;.rtetrametyl-3-f enylf uro (3, 4-e) -as-triazin smelter ved 90-9l°C. at 180°C. The solvent is then removed in vacuo and the residue is recrystallized from aqueous ethanol. The obtained 5,7-dihydro-5,5,7,7,-tetramethyl-3-phenylfluoro(3,4-e)-as-triazine melts at 90-91°C.
Eksempel 5: 5, 7- dihydro- 5, 5, 7, 7- tetrametvl- 3- fenylfuro( 3, 4- e)-as- triazin. Example 5: 5,7-dihydro-5,5,7,7-tetramethyl-3-phenylfuro(3,4-e)-astriazine.
Til en lbsning av 0,271 g 5,7-dihydro-5,5,7, 7-tetrametyl-3-fenylfuro(3,4-e)-as-triazin-4-oksyd og 0,246 g syklohexen i 4 ml absolutt etanol tilsettes 10 mg 10% palladium-kull-katalysator og den erholdte blanding oppvarmes til koking under nitrogenatmosfære i 18 timer. Deretter frafiltreres katalysatoren og filtratet inndampes til tbrrhet.. Resten omkrystalliseres fra eter/hexan hvorved 5,7-dihydro-5,5,7,7-tetrametyl-3-fenylfuro(3,4-e)-as-triazin med smeltepunkt 90-91°C erholdes. To a solution of 0.271 g of 5,7-dihydro-5,5,7,7-tetramethyl-3-phenylfuro(3,4-e)-as-triazine-4-oxide and 0.246 g of cyclohexene in 4 ml of absolute ethanol is added 10 mg of 10% palladium-charcoal catalyst and the resulting mixture is heated to boiling under a nitrogen atmosphere for 18 hours. The catalyst is then filtered off and the filtrate is evaporated to dryness. The residue is recrystallized from ether/hexane, whereby 5,7-dihydro-5,5,7,7-tetramethyl-3-phenylfuro(3,4-e)-as-triazine with a melting point of 90 -91°C is obtained.
Ytterligere forbindelser med formel I, hvori X, R^ og ^ har den i den fblgende tabell angitte betydning, kan erholdes under anvendels e av fremgangsmåtene i de foregående eksempter under anvendelse av egnede utgangsforbindelser i omtrent ekvivalente mengder. Further compounds of formula I, in which X, R^ and ^ have the meaning indicated in the following table, can be obtained using the methods in the preceding examples using suitable starting compounds in approximately equivalent amounts.
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GB (1) | GB1496709A (en) |
HU (1) | HU171171B (en) |
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IL47192A (en) | 1978-04-30 |
FI57416C (en) | 1980-08-11 |
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HU171171B (en) | 1977-11-28 |
SU588919A3 (en) | 1978-01-15 |
AU8064075A (en) | 1976-11-04 |
ES437214A1 (en) | 1977-05-16 |
IL52763A0 (en) | 1977-10-31 |
DK139301B (en) | 1979-01-29 |
DK172775A (en) | 1975-11-02 |
SE7504692L (en) | 1975-11-03 |
FI751205A (en) | 1975-11-02 |
AT357545B (en) | 1980-07-10 |
NL7504919A (en) | 1975-11-04 |
ATA332475A (en) | 1979-12-15 |
FR2269347A1 (en) | 1975-11-28 |
FR2269347B1 (en) | 1978-08-18 |
JPS50149696A (en) | 1975-11-29 |
DK139301C (en) | 1979-07-02 |
ES454313A1 (en) | 1977-12-01 |
FI57416B (en) | 1980-04-30 |
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DD119792A5 (en) | 1976-05-12 |
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