NO133235B - - Google Patents
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- Publication number
- NO133235B NO133235B NO164326A NO16432666A NO133235B NO 133235 B NO133235 B NO 133235B NO 164326 A NO164326 A NO 164326A NO 16432666 A NO16432666 A NO 16432666A NO 133235 B NO133235 B NO 133235B
- Authority
- NO
- Norway
- Prior art keywords
- nitro
- furaldehyde
- oxazolidone
- complex compound
- approx
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 14
- SXINBFXPADXIEY-UHFFFAOYSA-N 5-Nitrofurfural Chemical compound [O-][N+](=O)C1=CC=C(C=O)O1 SXINBFXPADXIEY-UHFFFAOYSA-N 0.000 claims description 9
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 4
- FUBFWTUFPGFHOJ-UHFFFAOYSA-N 2-nitrofuran Chemical class [O-][N+](=O)C1=CC=CO1 FUBFWTUFPGFHOJ-UHFFFAOYSA-N 0.000 claims description 3
- PLHJDBGFXBMTGZ-WEVVVXLNSA-N furazolidone Chemical compound O1C([N+](=O)[O-])=CC=C1\C=N\N1C(=O)OCC1 PLHJDBGFXBMTGZ-WEVVVXLNSA-N 0.000 claims description 3
- NXFQHRVNIOXGAQ-YCRREMRBSA-N nitrofurantoin Chemical compound O1C([N+](=O)[O-])=CC=C1\C=N\N1C(=O)NC(=O)C1 NXFQHRVNIOXGAQ-YCRREMRBSA-N 0.000 claims description 3
- IAIWVQXQOWNYOU-UHFFFAOYSA-N nitrofurazone Chemical compound NC(=O)NN=CC1=CC=C([N+]([O-])=O)O1 IAIWVQXQOWNYOU-UHFFFAOYSA-N 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 2
- 238000000354 decomposition reaction Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- UJTTUOLQLCQZEA-UHFFFAOYSA-N 9h-fluoren-9-ylmethyl n-(4-hydroxybutyl)carbamate Chemical compound C1=CC=C2C(COC(=O)NCCCCO)C3=CC=CC=C3C2=C1 UJTTUOLQLCQZEA-UHFFFAOYSA-N 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- KVYKDNGUEZRPGJ-UHFFFAOYSA-N 1-Aminohydantoin Chemical compound NN1CC(=O)NC1=O KVYKDNGUEZRPGJ-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- KYCJNIUHWNJNCT-UHFFFAOYSA-N 3-Amino-2-oxazolidone Chemical compound NN1CCOC1=O KYCJNIUHWNJNCT-UHFFFAOYSA-N 0.000 description 1
- 206010034972 Photosensitivity reaction Diseases 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000010668 complexation reaction Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- IAIWVQXQOWNYOU-FPYGCLRLSA-N nitrofural Chemical compound NC(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 IAIWVQXQOWNYOU-FPYGCLRLSA-N 0.000 description 1
- 230000036211 photosensitivity Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
- C12N9/14—Hydrolases (3)
- C12N9/48—Hydrolases (3) acting on peptide bonds (3.4)
- C12N9/50—Proteinases, e.g. Endopeptidases (3.4.21-3.4.25)
- C12N9/58—Proteinases, e.g. Endopeptidases (3.4.21-3.4.25) derived from fungi
- C12N9/62—Proteinases, e.g. Endopeptidases (3.4.21-3.4.25) derived from fungi from Aspergillus
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/814—Enzyme separation or purification
- Y10S435/815—Enzyme separation or purification by sorption
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/8215—Microorganisms
- Y10S435/911—Microorganisms using fungi
- Y10S435/913—Aspergillus
- Y10S435/918—Aspergillus oryzae
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Genetics & Genomics (AREA)
- Organic Chemistry (AREA)
- Zoology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Wood Science & Technology (AREA)
- Molecular Biology (AREA)
- Biotechnology (AREA)
- Microbiology (AREA)
- Biomedical Technology (AREA)
- Medicinal Chemistry (AREA)
- Biochemistry (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Mycology (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Enzymes And Modification Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Description
Fremgangsmåte til fremstilling av en furaldehyd-oxazolidon-kompleks-forbindelse.
Foreliggende oppfinnelse vedrører
fremstillingen av et nytt kjemisk preparat som er en stabil, ikke lyssensitiv kompleksforbindelse fremstilt ved reaksjon av 5-nitro-2-furaldehyd og 2-oxazolidon, og den kan representeres av formelen:
Den nye kompleksforbindelse er nyttig som et mellomprodukt ved fremstillingen av farmakologisk virksomme nitrofuraner, f. eks. N-(5-nitro-2-furfuryliden)-l-amin-nohydrantoin (US patent nr. 2.610.181), N-(5-nitro-2-furfuryliden)-3-amino-2-oxazolidon (US patent nr. 2 759 932) og 5-nitro-2-furaldehydsemicarbazon (US patent nr. 2 416 234).
Det er naturligvis kjent at 5-nitro-2-furaldehyd er et verdifullt mellomprodukt ved fremstillingen av de ovennevnte farmakologisk virksomme forbindelser. Dette aldehyd er imidlertid en relativt ustabil kjemisk forbindelse, som er meget fotosen-sitiv. Den blir gradvis mørkere i nærvær av lys og blir sluttelig harpiksaktig under tap av -N02-radikalet. Den kan ikke lagres i noen særlig lang tid på grunn av at dens fotofølsomhet medfører dannelsen av for-urensende spaltningsprodukter. Hvis man tar tilflukt til rensningsprosesser, blir dette tidskrevende og kostbart.
Videre har 5-nitro-2-furaldehyd et lavt smeltepunkt (35—36° C), slik at man må treffe forsiktighetsregler for å unngå smeltning ved slike temperaturer, som ofte opptrer. Påfølgende pånystivning ved la-vere temperaturer medfører dannelsen av en hård masse som er vanskelig å hånd-tere.
Et formål for oppfinnelsen er å over-føre 5-nitro-2-furaldehyd i en slik tilstand at den er stabil og kan håndteres meget lett og på samme tid er den lett tilgjengelig for bruk som et mellomprodukt ved fremstillingen av de ovenfor nevnte nitrofuraner ved kompleksdannelse med 2-oxazolidon.
Den nye kompleksforbindelse som fremstilles ved å la 5-nitro-2-furaldehyd og 2-oxazolidon reagere med hverandre, fortrinsvis i nærvær av vann, ved en temperatur av fra ca. 45—50° C så at det dannes 1 : 1 mol addukt, er et fritt strømmende, krystallinsk fast stoff med et smeltepunkt (135—140° C) som ligger godt og vel over de temperaturer som man med rimelighet kan regne med opptrer, og det har ingen av de lyssensitive egenskaper som 5-nitro-2-furaldehyd. Det kan således oppbevares i lange tidsperioder uten at det inntrer noen forandring.
Når den nye kompleksforbindelse opphetes i nærvær av vann ved en temperatur av ca. 90—100° C, regenereres dens kom-ponenter, 5-nitro-2-furaldehyd og 2-oxazolidon, således at aldehydet blir tilgjengelig for reaksjon med carbonylderivatiserende midler, f. eks. 1-amino-hydantoin, 3-ami-ni-2-oxazolidon og semicarbacid, hvorved det dannes henholdsvis N-(5-nitro-2-fur-furyliden) -1-aminohydantoin, N- (5-nitro-2-f urf uryliden) -3-amino-2-oxazolidon og 5-nitro-2-furaldehyd-semicarbazon.
Den fortrinsvis anvendte fremgangsmåte for fremstilling av de ovennevnte farmakologisk effektive substanser består i å tilsette det passende carbonylderivatiserende middel til en vandig oppløsning, opp-hetet til ca. 90—100° C, av den nye kompleksforbindelse. I løpet av meget kort tid finner kondenseringen sted mellom 5-nitro-2-furaldehyd og det carbonylderivatiserende middel. Ved kjøling fåes produktet med et godt utbytte.
Por at oppfinnelsen lett skal forståes av fagfolk skal det anføres følgende illu-strerende eksempel.
Til en oppløsning av 25 g 2-oxazolidon i 100 ml vann tilsettes 25 g 5-nitro-2-fural-dehyd og blandingen omrøres ved ca. 45— 50° C i ca. 15 minutter. Etter kjøling til ca. 2—10° C filtreres blandingen. Det faste stoff vaskes med 100 ml koldt vann etter-fulgt med 2x100 ml deler ether. Etter tør-king fåes 23,2 g (57 pst.) av den nye kompleksforbindelse, smp. 135—140° C. Ytter-ligere 13,7 g (34 pst.) av den nye kompleksforbindelse fåes ved konsentrering av filtratet. Den nye kompleksforbindelse kan omkrystalliseres fra ethylalkohol.
Dens E }/°°= 524 ved 3100 Å. 1 cm Analyse: Beregnet: 42,11 pst. C, 3,53 pst. H, 12,28 pst. N. Funnet: 42,25 pst. C, 3,26 pst. H, 12,21 pst. N.
Farmakologisk effektive substanser kan fåes fra denne kompleksforbindelse slik som det fremgår av de følgende ek-sempler.
Til et vandig medium som inneholder 1 g av den nye kompleksforbindelse tilsettes 0,5 g semicarbazid-hydroklorid og 2 dråper konsentrert saltsyre og blandingen opphetes ved 90—100° C i ca. 5 minutter. Blandingen kjøles til ca. 2—10° C og filtreres. Den faste substans som fåes, 5-nitro-2-furaldehydsemicarbazon, veier 0,85 g (98 pst. utbytte), smp. 233° C under spaltning. Hvis det anvendes 1-amino-hydantoin i stedenfor semicarbazidhydro-klorid fåes det N-(5-nitro-2-furfuryliden)-1-aminohydantoin, 0,95 g (91 pst.), smp. 266—267° C under spaltning. Hvis det bru-kes 3-amino-2-oxazolidon istedenfor semi-carbazidhydroklorid fåes N-(5-nitro-2-fur-furyliden)-3-åmino-2-oxazolidon, 0,9 g (91 pst.), smp. 256—257° C under spaltning.
Claims (1)
- Fremgangsmåte for fremstilling av en stabil, ikke lyssensitiv furaldehyd-oxazoli-donkompleksforbindelse med formelen:og som er nyttig som mellomprodukt ved fremstilingen av farmakologisk virksomme nitrofuraner, f. eks. N-(5-nitro-2-fur-f uryliden)-1-aminohydantoin, N-(5-nitro-2-furf uryliden) -3-amino-2-oxazolidon og 5-nitro-2-f uraldehydsemicarbazon, karakterisert ved at 5-nitro-2-furalde-hyd og 2-oxazolidon bringes til å reagere med hverandre ved en temperatur av ca. 45—50° C, fortrinsvis i nærvær av vann.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE11191/65A SE328534B (no) | 1965-08-27 | 1965-08-27 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO133235B true NO133235B (no) | 1975-12-22 |
| NO133235C NO133235C (no) | 1976-03-31 |
Family
ID=20293514
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO164326A NO133235C (no) | 1965-08-27 | 1966-08-16 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US3509024A (no) |
| AT (1) | AT277454B (no) |
| CH (1) | CH525251A (no) |
| DE (1) | DE1617279C3 (no) |
| DK (1) | DK119790B (no) |
| FI (2) | FI43715C (no) |
| FR (1) | FR6225M (no) |
| GB (1) | GB1150293A (no) |
| IL (1) | IL26344A (no) |
| NL (1) | NL6612046A (no) |
| NO (1) | NO133235C (no) |
| SE (1) | SE328534B (no) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK81193D0 (da) * | 1993-07-06 | 1993-07-06 | Novo Nordisk As | Enzym |
| GB9425138D0 (en) * | 1994-12-12 | 1995-02-08 | Dynal As | Isolation of nucleic acid |
| AU2473099A (en) * | 1998-02-13 | 1999-08-30 | National Enzyme Company | Protease-based dietary supplementation for decreasing recovery time from soft-tissue injury |
| AU2862100A (en) * | 1999-01-27 | 2000-08-18 | Folim G. Halaka | Materials and methods for the purification of polyelectrolytes |
| AU2003202026A1 (en) | 2002-01-16 | 2003-09-02 | Dynal Biotech Asa | Method for isolating nucleic acids and protein from a single sample |
-
1965
- 1965-08-27 SE SE11191/65A patent/SE328534B/xx unknown
-
1966
- 1966-08-16 NO NO164326A patent/NO133235C/no unknown
- 1966-08-16 IL IL26344A patent/IL26344A/xx unknown
- 1966-08-17 GB GB36836/66A patent/GB1150293A/en not_active Expired
- 1966-08-19 DE DE1617279A patent/DE1617279C3/de not_active Expired
- 1966-08-22 CH CH1206566A patent/CH525251A/de not_active IP Right Cessation
- 1966-08-25 AT AT805566A patent/AT277454B/de not_active IP Right Cessation
- 1966-08-25 DK DK434766AA patent/DK119790B/da unknown
- 1966-08-26 NL NL6612046A patent/NL6612046A/xx unknown
- 1966-08-26 FR FR74303A patent/FR6225M/fr not_active Expired
- 1966-08-26 US US575406A patent/US3509024A/en not_active Expired - Lifetime
- 1966-08-26 FI FI662235A patent/FI43715C/fi active
-
1970
- 1970-08-31 FI FI702402A patent/FI45164C/fi active
Also Published As
| Publication number | Publication date |
|---|---|
| FI45164C (fi) | 1972-04-10 |
| GB1150293A (en) | 1969-04-30 |
| IL26344A (en) | 1970-01-29 |
| SE328534B (no) | 1970-09-21 |
| NL6612046A (no) | 1967-02-28 |
| FI45164B (no) | 1971-12-31 |
| FI43715C (fi) | 1971-06-10 |
| DE1617279B2 (de) | 1979-08-09 |
| NO133235C (no) | 1976-03-31 |
| DE1617279C3 (de) | 1980-04-24 |
| DE1617279A1 (de) | 1971-02-18 |
| CH525251A (de) | 1972-07-15 |
| FR6225M (no) | 1968-08-05 |
| FI43715B (no) | 1971-03-01 |
| DK119790B (da) | 1971-02-22 |
| AT277454B (de) | 1969-12-29 |
| US3509024A (en) | 1970-04-28 |
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