NO118718B - - Google Patents
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- NO118718B NO118718B NO16350266A NO16350266A NO118718B NO 118718 B NO118718 B NO 118718B NO 16350266 A NO16350266 A NO 16350266A NO 16350266 A NO16350266 A NO 16350266A NO 118718 B NO118718 B NO 118718B
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- Prior art keywords
- sulfanilamido
- parts
- alcohol
- dissolved
- filtered
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- XPGJOCWCEGOGMR-UHFFFAOYSA-N 3-amino-n-(6-chloropyridazin-3-yl)benzenesulfonamide Chemical compound NC1=CC=CC(S(=O)(=O)NC=2N=NC(Cl)=CC=2)=C1 XPGJOCWCEGOGMR-UHFFFAOYSA-N 0.000 claims description 11
- 239000011541 reaction mixture Substances 0.000 claims description 6
- -1 3-Sulfanilamido-6-substituted pyridazines Chemical class 0.000 claims description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 150000001340 alkali metals Chemical class 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 150000005840 aryl radicals Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 33
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 9
- 235000019441 ethanol Nutrition 0.000 description 9
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 8
- 239000012043 crude product Substances 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 5
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- VLYWMPOKSSWJAL-UHFFFAOYSA-N sulfamethoxypyridazine Chemical compound N1=NC(OC)=CC=C1NS(=O)(=O)C1=CC=C(N)C=C1 VLYWMPOKSSWJAL-UHFFFAOYSA-N 0.000 description 4
- HICQMZYOPRMAAK-UHFFFAOYSA-N 3-amino-N-(6-propoxypyridazin-3-yl)benzenesulfonamide Chemical compound S(=O)(C1=CC(=CC=C1)N)(=O)NC=1N=NC(=CC1)OCCC HICQMZYOPRMAAK-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- GALUOVNQQMWGKZ-UHFFFAOYSA-N 3-amino-N-(6-ethoxypyridazin-3-yl)benzenesulfonamide Chemical compound S(=O)(C1=CC(=CC=C1)N)(=O)NC=1N=NC(=CC1)OCC GALUOVNQQMWGKZ-UHFFFAOYSA-N 0.000 description 2
- UUTGXHJWYZPQCP-UHFFFAOYSA-N 3-amino-N-(6-phenoxypyridazin-3-yl)benzenesulfonamide Chemical compound S(=O)(C1=CC(=CC=C1)N)(=O)NC=1N=NC(=CC1)OC1=CC=CC=C1 UUTGXHJWYZPQCP-UHFFFAOYSA-N 0.000 description 2
- WOCJWWQWJCQPQH-UHFFFAOYSA-N 3-amino-N-(6-phenylmethoxypyridazin-3-yl)benzenesulfonamide Chemical compound S(=O)(C1=CC(=CC=C1)N)(=O)NC=1N=NC(=CC1)OCC1=CC=CC=C1 WOCJWWQWJCQPQH-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- GUSWJGOYDXFJSI-UHFFFAOYSA-N 3,6-dichloropyridazine Chemical compound ClC1=CC=C(Cl)N=N1 GUSWJGOYDXFJSI-UHFFFAOYSA-N 0.000 description 1
- GQEPYVYGKDXXOB-UHFFFAOYSA-N 3-amino-N-(6-hexoxypyridazin-3-yl)benzenesulfonamide Chemical compound S(=O)(C1=CC(=CC=C1)N)(=O)NC=1N=NC(=CC1)OCCCCCC GQEPYVYGKDXXOB-UHFFFAOYSA-N 0.000 description 1
- VCHGLBPWYYXRTQ-UHFFFAOYSA-N 3-amino-N-[6-(2-phenylethoxy)pyridazin-3-yl]benzenesulfonamide Chemical compound S(=O)(C1=CC(=CC=C1)N)(=O)NC=1N=NC(=CC1)OCCC1=CC=CC=C1 VCHGLBPWYYXRTQ-UHFFFAOYSA-N 0.000 description 1
- ASFHDLDAWYTMJS-UHFFFAOYSA-N 3-methoxypyridazine Chemical compound COC1=CC=CN=N1 ASFHDLDAWYTMJS-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- XOXHILFPRYWFOD-UHFFFAOYSA-N sulfachloropyridazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=CC=C(Cl)N=N1 XOXHILFPRYWFOD-UHFFFAOYSA-N 0.000 description 1
- SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 description 1
- 229960004306 sulfadiazine Drugs 0.000 description 1
- 229960004936 sulfamethoxypyridazine Drugs 0.000 description 1
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
Classifications
-
- E—FIXED CONSTRUCTIONS
- E04—BUILDING
- E04F—FINISHING WORK ON BUILDINGS, e.g. STAIRS, FLOORS
- E04F15/00—Flooring
- E04F15/02—Flooring or floor layers composed of a number of similar elements
- E04F15/024—Sectional false floors, e.g. computer floors
- E04F15/02405—Floor panels
- E04F15/02435—Sealing joints
-
- E—FIXED CONSTRUCTIONS
- E04—BUILDING
- E04F—FINISHING WORK ON BUILDINGS, e.g. STAIRS, FLOORS
- E04F15/00—Flooring
- E04F15/02—Flooring or floor layers composed of a number of similar elements
- E04F15/024—Sectional false floors, e.g. computer floors
- E04F15/02405—Floor panels
-
- E—FIXED CONSTRUCTIONS
- E04—BUILDING
- E04F—FINISHING WORK ON BUILDINGS, e.g. STAIRS, FLOORS
- E04F15/00—Flooring
- E04F15/02—Flooring or floor layers composed of a number of similar elements
- E04F15/024—Sectional false floors, e.g. computer floors
- E04F15/02447—Supporting structures
- E04F15/02464—Height adjustable elements for supporting the panels or a panel-supporting framework
- E04F15/0247—Screw jacks
Landscapes
- Engineering & Computer Science (AREA)
- Architecture (AREA)
- General Engineering & Computer Science (AREA)
- Civil Engineering (AREA)
- Structural Engineering (AREA)
- Floor Finish (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Fremgangsmåte for fremstilling av 3-sulfanilamido-6-substituerte pyridaziner. Process for the preparation of 3-sulfanilamido-6-substituted pyridazines.
Foreliggende oppfinnelse vedrører en The present invention relates to a
fremgangsmåte for fremstilling av 3-sulfanilamido-6-substituerte pyridaziner. process for the preparation of 3-sulfanilamido-6-substituted pyridazines.
De forbindelser som omfattes av foreliggende oppfinnelse kan angis ved følgende generelle formel: The compounds covered by the present invention can be indicated by the following general formula:
hvor R er et alkyl-, aralkyl- eller aryl-radikal. F. eks. kan alkylradikalene være metyl, etyl, propyl, butyl eller amyl; aral-kylradikalene kan være benzyl, fenetyl, fenpropyl eller fenbutyl, og arylradikalene kan være fenyl eller naftyl. Forbindelsene i følge foreliggende oppfinnelse er i alminnelighet krystallinske faste stoffer med et smeltepunkt over 100° C. De kan rekrystalliseres fra vann eller where R is an alkyl, aralkyl or aryl radical. For example the alkyl radicals can be methyl, ethyl, propyl, butyl or amyl; the aralkyl radicals can be benzyl, phenethyl, phenpropyl or phenbutyl, and the aryl radicals can be phenyl or naphthyl. The compounds according to the present invention are generally crystalline solids with a melting point above 100° C. They can be recrystallized from water or
alkoholer eller en blanding av vann og alcohols or a mixture of water and
alkohol. alcohol.
I overensstemmelse med oppfinnelsen In accordance with the invention
kan disse forbindelser fremstilles ved å an-vende 3-sulfanilamido-6-klorpyridazin som these compounds can be prepared by using 3-sulfanilamido-6-chloropyridazine as
et mellomprodukt som bringes til å reagere an intermediate that is brought to react
med et alkalimetallalkoholat som resulterer with an alkali metal alcoholate resulting
fra reaksjonen av en alkohol av formelen from the reaction of an alcohol of the formula
ROH og et alkalimetall. Enkle alkoholer, ROH and an alkali metal. Simple alcohols,
fenol, benzylalkohol, fenetylalkohol og lig-nende kan anvendes ved reaksjonen. Det phenol, benzyl alcohol, phenethyl alcohol and the like can be used in the reaction. The
er vanligvis ønskelig å opphete reaksjonsblandingen til en temperatur innenfor om-rådet av 50° C til 250° C i en periode av fra it is usually desirable to heat the reaction mixture to a temperature within the range of 50° C. to 250° C. for a period of from
10 minutter til 15 timer. Et alkalimetall 10 minutes to 15 hours. An alkali metal
som f. eks. natrium eller kalium tilsettes like for example. sodium or potassium is added
til alkoholen for å danne det tilsvarende to the alcohol to form the equivalent
alkoholat som derpå bringes til å reagere alcoholate which is then brought to react
med 3-sulfanilamido-6-klorpyridazinet. with the 3-sulfanilamido-6-chloropyridazine.
3-sulfanilamido-6-klorpyridazinet som The 3-sulfanilamido-6-chloropyridazine which
anvendes som et mellomprodukt ved reaksjonen, kan fåes ved å la 3,6-diklorpyrida-zin reagere med sulfanilamid, fortrinsvis ved opphetning ved temperaturer av fra 130° C til 220° C i nærvær av en syre-akseptor. used as an intermediate in the reaction, can be obtained by allowing 3,6-dichloropyridazine to react with sulfanilamide, preferably by heating at temperatures of from 130° C. to 220° C. in the presence of an acid acceptor.
Fremstillingen av de terapeutiske nyt-tige forbindelser i henhold til foreliggende oppfinnelse skal beskrives mer detaljert i forbindelse med de følgende angitte eks-empler. Bare deler betyr vektsdeler, hvis der ikke er anført noe annet. The preparation of the therapeutically useful compounds according to the present invention shall be described in more detail in connection with the examples given below. Parts only means parts by weight, unless otherwise stated.
Eksempel 1: 3- sulfanilamido- 6- metoksypyridazin. Example 1: 3-sulfanilamido-6-methoxypyridazine.
2,3 deler av rent natriummetall opp-løses i 50 deler vannfri metylalkohol. 11,4 deler av 3-sulfanilamido-6-klorpyridazin tilsettes, og blandingen opphetes i et lukket rør i 13 timer ved 130-140° C. Etter at røret er blitt kjølet, åpnes det, og reaksjonsblandingen filtreres, ansyres med fortynnet eddiksyre, og derpå inndampes til tørr-het på dampbad. Residuet oppløses i 80 deler 5 pst.'s natriumhydroksyd, kjøles og ansyres med fortynnet eddiksyre. Det rå produkt filtreres og rekrystalliseres derpå fra vann så at man får 3-sulfanilamido-6- 2.3 parts of pure sodium metal are dissolved in 50 parts of anhydrous methyl alcohol. 11.4 parts of 3-sulfanilamido-6-chloropyridazine are added, and the mixture is heated in a closed tube for 13 hours at 130-140° C. After the tube has been cooled, it is opened, and the reaction mixture is filtered, acidified with dilute acetic acid, and then evaporated to dryness on a steam bath. The residue is dissolved in 80 parts of 5% sodium hydroxide, cooled and acidified with dilute acetic acid. The crude product is filtered and then recrystallized from water to give 3-sulfanilamido-6-
metoksypyridazin av smeltepunkt 182— 183° C. methoxypyridazine of melting point 182— 183° C.
Eksempel 2: Example 2:
3- sulfanilamido- 6- etoksypyridazin. 3- sulfanilamido- 6- ethoxypyridazine.
0,6 deler rent natriummetall oppløses i 75 deler absolutt etylalkohol. 2,9 deler 3-sulfanilamido-6-klorpyridazin tilsettes, og blandingen opphetes i et lukket rør i 13 timer ved 145-155° C. Etter at røret er av-kjølt, åpnes det, og reaksjonsblandingen filtreres, ansyres med fortynnet eddiksyre, og inndampes derpå til tørrhet på dampbad. Residuet oppløses i 20 deler 10 pst.'s natriumhydroksyd, avkjøles og ansyres med fortynnet eddiksyre. Det rå produkt filtreres, og derpå rekrystalliseres fra vann-etanol så at man får 3-sulfanilamido-6-etoksypyridazin av smeltepunkt 183— 184° C. 0.6 parts of pure sodium metal are dissolved in 75 parts of absolute ethyl alcohol. 2.9 parts of 3-sulfanilamido-6-chloropyridazine are added, and the mixture is heated in a closed tube for 13 hours at 145-155° C. After the tube has cooled, it is opened, and the reaction mixture is filtered, acidified with dilute acetic acid, and then evaporated to dryness on a steam bath. The residue is dissolved in 20 parts of 10% sodium hydroxide, cooled and acidified with dilute acetic acid. The crude product is filtered, and then recrystallized from water-ethanol so that 3-sulfanilamido-6-ethoxypyridazine of melting point 183-184° C is obtained.
Eksempel 3: 3- sulfanilamido- 6- n- propoksypyridazin. Example 3: 3-sulfanilamido-6-n-propoxypyridazine.
0,6 deler rent natriummetall oppløses i 75 deler n-propylalkohol. 2,9 deler 3-sulfanilamido-6-klorpyridazin tilsettes, og blandingen opphetes i et lukket rør i 13 timer ved 145—155° C. Etter at røret er avkjølet, åpnes det, og reaksjonsblandingen filtreres, ansyres med fortynnet eddiksyre, og derpå inndampes til tørrhet på dampbad. Residuet oppløses i 10 deler 5 pst's natriumhydroksyd, avkjøles og ansyres med fortynnet addiksyre. Det rå produkt filtreres og rekrystalliseres fra vann-etanol så at man får 3-sulfanilamido-6-n-propoksypyridazin av smeltepunkt 184—185° C. 0.6 parts of pure sodium metal are dissolved in 75 parts of n-propyl alcohol. 2.9 parts of 3-sulfanilamido-6-chloropyridazine are added, and the mixture is heated in a closed tube for 13 hours at 145-155° C. After the tube has cooled, it is opened, and the reaction mixture is filtered, acidified with dilute acetic acid, and then evaporated to dryness on a steam bath. The residue is dissolved in 10 parts of 5% sodium hydroxide, cooled and acidified with dilute acetic acid. The crude product is filtered and recrystallized from water-ethanol so that 3-sulfanilamido-6-n-propoxypyridazine of melting point 184-185° C is obtained.
Eksempel 4: 3- sulfanilamido- 6- i- propoksypyridasin. Example 4: 3-sulfanilamido-6-i-propoxypyridazine.
0,6 deler rent natriummetall oppløses i 75 deler i-propylalkohol. 2,9 deler 3-sulfanilamido-6-klorpyridazin tilsettes, og blandingen opphetes i et lukket rør i 13 timer ved 145—155° C. Etter at røret er avkjølt åpnes det, og reaksjonsblandingen filtreres, ansyres med fortynnet eddiksyre og inndampes derpå til tørrhet på dampbad. Residuet oppløses i 10 ml 5 pst.'s natriumhydroksyd, avkjøles og ansyres med fortynnet eddiksyre. Det rå produkt filtreres og rekrystalliseres fra vann-etanol så at man får 3-sulfanilamido-6-z-propoksypyridazin av smeltepunkt 187—188° C. 0.6 parts of pure sodium metal are dissolved in 75 parts of i-propyl alcohol. 2.9 parts of 3-sulfanilamido-6-chloropyridazine are added, and the mixture is heated in a closed tube for 13 hours at 145-155° C. After the tube has cooled, it is opened, and the reaction mixture is filtered, acidified with dilute acetic acid and then evaporated to dryness in a steam bath. The residue is dissolved in 10 ml of 5% sodium hydroxide, cooled and acidified with dilute acetic acid. The crude product is filtered and recrystallized from water-ethanol so that 3-sulfanilamido-6-z-propoxypyridazine of melting point 187-188° C is obtained.
Eksempel 5: 3- sulfanilamido- 6- n- heksoksypyridazin. Example 5: 3-sulfanilamido-6-n-hexoxypyridazine.
0,6 deler rent natriummetall oppløses i 200 deler n-heksylalkohol. 2,9 deler 3-sulfanilamido-6-klorpyridazin tilsettes, og blandingen opphetes under tilbakeløp i 40 timer ved 157° C. Den overskytende alkohol destilleres derpå i vakuum. Residuet suspenderes i eter, filtreres, vaskes to ganger med eter, oppløses derpå i 20 deler vann og ansyres med fortynnet eddiksyre. Det rå produkt filtreres, og derpå rekrystalliseres fra vann-etanol så at man får 3-sulfanilamido-6-7i-heksoksypyridazin av smeltepunkt 140—141° C. 0.6 parts of pure sodium metal are dissolved in 200 parts of n-hexyl alcohol. 2.9 parts of 3-sulfanilamido-6-chloropyridazine are added, and the mixture is heated under reflux for 40 hours at 157° C. The excess alcohol is then distilled in vacuum. The residue is suspended in ether, filtered, washed twice with ether, then dissolved in 20 parts of water and acidified with dilute acetic acid. The crude product is filtered, and then recrystallized from water-ethanol so that 3-sulfanilamido-6-7i-hexoxypyridazine of melting point 140-141° C is obtained.
Eksempel 6: Example 6:
3- sulfanilamido- 6- fenoksypyridazin. 3- sulfanilamido- 6- phenoxypyridazine.
0,6 deler rent natriummetall oppløses i 50 deler metylalkohol. 2,9 deler 3-sulfanilamido-6-klorpyridazin og 60 deler fenol tilsettes, og oppløsningen opphetes til 140° C for å drive av alle spor av metylalkohol og vann. Residuet opphetes ved 140° i 9 timer, og derpå avdestilleres den overskytende fenol. Residuet suspenderes i eter, vaskes to ganger med eter, derpå oppløses i 20 deler vann og ansyres med fortynnet syre. Det rå produkt filtreres, og derpå rekrystalliseres fra vann-etanol så man får 3-sulfanilamido-6-fenoksypyridazin. For-bindelsen smelter ved 139—140° C, stivner påny og smelter igjen ved 160—161° C. 0.6 parts of pure sodium metal are dissolved in 50 parts of methyl alcohol. 2.9 parts of 3-sulfanilamido-6-chloropyridazine and 60 parts of phenol are added, and the solution is heated to 140° C. to drive off all traces of methyl alcohol and water. The residue is heated at 140° for 9 hours, and then the excess phenol is distilled off. The residue is suspended in ether, washed twice with ether, then dissolved in 20 parts of water and acidified with dilute acid. The crude product is filtered, and then recrystallized from water-ethanol to obtain 3-sulfanilamido-6-phenoxypyridazine. The compound melts at 139-140° C, solidifies again and melts again at 160-161° C.
Eksempel 7: 3- sulfanilamido- 6- benzyloksypyridazin. Example 7: 3-sulfanilamido-6-benzyloxypyridazine.
0,6 deler rent natriummetall oppløses i 150 deler benzylalkohol. 2,9 deler 3-sulfanilamido-6-klorpyridazin tilsettes, og blandingen opphetes i 13 timer ved 145—147° C. Den overskytende alkohol destilleres derpå i vakuum. Residuet suspenderes i eter, filtreres, vaskes to ganger med eter, derpå oppløses i 20 deler vann og ansyres med fortynnet eddiksyre. Det rå produkt filtreres, og derpå rekrystalliseres fra etylalkohol så at man får 3-sulfanilamido-6-benzyloksypyridazin av smeltepunkt 200— 201° C. 0.6 parts of pure sodium metal are dissolved in 150 parts of benzyl alcohol. 2.9 parts of 3-sulfanilamido-6-chloropyridazine are added, and the mixture is heated for 13 hours at 145-147° C. The excess alcohol is then distilled in vacuum. The residue is suspended in ether, filtered, washed twice with ether, then dissolved in 20 parts of water and acidified with dilute acetic acid. The crude product is filtered, and then recrystallized from ethyl alcohol so that 3-sulfanilamido-6-benzyloxypyridazine of melting point 200-201°C is obtained.
Eksempel 8: 3- sulfanilamido- 6- fenetoksypyridazin. Example 8: 3-sulfanilamido-6-phenethoxypyridazine.
0,6 deler rent natriummetall oppløses i 150 deler beia-fenetylalkohol. 2,9 deler 3- 0.6 parts of pure sodium metal are dissolved in 150 parts of beta-phenethyl alcohol. 2.9 parts 3-
sulfanilamido-6-klorpyridazin tilsettes, og blandingen opphetes under tilbakeløp i 2i/o time ved 220° C. Den overskytende alkohol destilleres derpå i vakuum. Residuet suspenderes i eter, vaskes to ganger med eter, oppløses i 20 deler vann og ansyres med fortynnet eddiksyre. Det rå produkt filtreres og derpå rekrystalliseres fra absolutt alkohol så at man får 3-sulfanilamido-G-fenetoksypyridazin av smeltepunkt 173 —174° C. Sulphanilamido-6-chloropyridazine is added, and the mixture is heated under reflux for 2½ hours at 220° C. The excess alcohol is then distilled in vacuum. The residue is suspended in ether, washed twice with ether, dissolved in 20 parts of water and acidified with dilute acetic acid. The crude product is filtered and then recrystallized from absolute alcohol to give 3-sulfanilamido-G-phenethoxypyridazine of melting point 173-174°C.
Forbindelsene i henhold til foreliggende oppfinnelse oppviser når de administreres oralt, større motstandsdyktighet hos mus like overfor pneumococcus Strain SVI enn beslektede forbindelser. Den følgende tabell I viser de detaljerte resultater som fåes når der anvendes sulfadiazin, sulfapyrida-zin og 3-sulfanilamido-6-metoksypyridazin. The compounds of the present invention, when administered orally, show greater resistance in mice to pneumococcus strain SVI than related compounds. The following Table I shows the detailed results obtained when sulfadiazine, sulfapyridazine and 3-sulfanilamido-6-methoxypyridazine are used.
3-sulfanilamido-6-metoksypyridazin. 3-sulfanilamido-6-methoxypyridazine.
Når de foreliggende forbindelser administreres til mus som er infisert med et flertall forskjellige bakterier sammen med beslektede forbindelser, så viser de å være i besiddelse av en større aktivitet. Dette er vist i den følgende tabell II. When the present compounds are administered to mice infected with a plurality of different bacteria together with related compounds, they are shown to possess greater activity. This is shown in the following table II.
Claims (2)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1965S0052908 DE1933817U (en) | 1965-06-18 | 1965-06-18 | COMPONENT SET FOR FLOORING FLOORING. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO118718B true NO118718B (en) | 1970-02-02 |
Family
ID=7488982
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO16350266A NO118718B (en) | 1965-06-18 | 1966-06-17 |
Country Status (7)
| Country | Link |
|---|---|
| AT (1) | AT265599B (en) |
| BE (1) | BE682778A (en) |
| CH (1) | CH440655A (en) |
| DE (1) | DE1933817U (en) |
| LU (1) | LU51161A1 (en) |
| NL (1) | NL6607944A (en) |
| NO (1) | NO118718B (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2900759C3 (en) * | 1979-01-10 | 1986-05-07 | Marbeton Kies- U. Betonwerk Marstetten Gmbh, 7971 Aitrach | Elevated floor |
| CH656413A5 (en) * | 1981-04-07 | 1986-06-30 | Karl Glockenstein | WALL ELEMENT. |
| DE4329710C2 (en) * | 1993-09-02 | 1996-05-23 | Mero Werke Kg | Raised floor |
| DE4404368C2 (en) * | 1994-02-11 | 1996-12-19 | Mero Werke Kg | Process for producing a cavity floor |
| ITUB20159794A1 (en) * | 2015-12-30 | 2017-06-30 | Ge Giussani Srl | SUPPORTED FEET OF IMPROVED TYPE FOR RAISED FLOORS |
-
1965
- 1965-06-18 DE DE1965S0052908 patent/DE1933817U/en not_active Expired
-
1966
- 1966-05-23 LU LU51161D patent/LU51161A1/xx unknown
- 1966-06-08 NL NL6607944A patent/NL6607944A/xx unknown
- 1966-06-15 CH CH863966A patent/CH440655A/en unknown
- 1966-06-16 AT AT574766A patent/AT265599B/en active
- 1966-06-17 NO NO16350266A patent/NO118718B/no unknown
- 1966-06-20 BE BE682778D patent/BE682778A/fr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| LU51161A1 (en) | 1968-02-21 |
| DE1933817U (en) | 1966-03-03 |
| CH440655A (en) | 1967-07-31 |
| BE682778A (en) | 1966-12-20 |
| AT265599B (en) | 1968-10-10 |
| NL6607944A (en) | 1966-12-19 |
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