NO142646B - Fremgangsmaate for fremstilling av et smoerbart naeringsmiddel med lavt fettinnhold av vann-i-oljetype - Google Patents
Fremgangsmaate for fremstilling av et smoerbart naeringsmiddel med lavt fettinnhold av vann-i-oljetype Download PDFInfo
- Publication number
- NO142646B NO142646B NO763782A NO763782A NO142646B NO 142646 B NO142646 B NO 142646B NO 763782 A NO763782 A NO 763782A NO 763782 A NO763782 A NO 763782A NO 142646 B NO142646 B NO 142646B
- Authority
- NO
- Norway
- Prior art keywords
- lubricable
- nutrient
- preparing
- procedure
- water
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 235000004213 low-fat Nutrition 0.000 title 1
- 235000015097 nutrients Nutrition 0.000 title 1
- SXINBFXPADXIEY-UHFFFAOYSA-N 5-Nitrofurfural Chemical compound [O-][N+](=O)C1=CC=C(C=O)O1 SXINBFXPADXIEY-UHFFFAOYSA-N 0.000 claims description 3
- QHSHDVYEJKLXLB-UHFFFAOYSA-N ethyl n-(2-chloroethyl)carbamate Chemical compound CCOC(=O)NCCCl QHSHDVYEJKLXLB-UHFFFAOYSA-N 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- PEVLAELZNUZRPV-IZZDOVSWSA-N 1-[(e)-benzylideneamino]imidazolidine-2,4-dione Chemical compound O=C1NC(=O)CN1\N=C\C1=CC=CC=C1 PEVLAELZNUZRPV-IZZDOVSWSA-N 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 150000001447 alkali salts Chemical class 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 1
- 239000003701 inert diluent Substances 0.000 claims 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 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
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 206010041925 Staphylococcal infections Diseases 0.000 description 1
- 241000191940 Staphylococcus Species 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000000973 chemotherapeutic effect Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- VHAOSWZDVLMILN-UHFFFAOYSA-N ethyl N-[2-[3-[(5-nitrofuran-2-yl)methylideneamino]-2,5-dioxoimidazolidin-1-yl]ethyl]carbamate Chemical compound [N+](=O)([O-])C1=CC=C(C=NN2C(N(C(C2)=O)CCNC(OCC)=O)=O)O1 VHAOSWZDVLMILN-UHFFFAOYSA-N 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000010603 pastilles Nutrition 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 231100000816 toxic dose Toxicity 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
- A23D7/00—Edible oil or fat compositions containing an aqueous phase, e.g. margarines
- A23D7/015—Reducing calorie content; Reducing fat content, e.g. "halvarines"
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23C—DAIRY PRODUCTS, e.g. MILK, BUTTER OR CHEESE; MILK OR CHEESE SUBSTITUTES; MAKING THEREOF
- A23C15/00—Butter; Butter preparations; Making thereof
- A23C15/12—Butter preparations
- A23C15/16—Butter having reduced fat content
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Edible Oils And Fats (AREA)
- Fodder In General (AREA)
Description
Fremgangsmåte for fremstilling av det terapeutisk virksomme ethyl-2 [l-(5-nitro furfurylidenamino) -2,4-dioxo-3-imidazolidyl] -ethylcarbamat
Foreliggende oppfinnelse angår fremstilling av den nye kjemiske forbindelse
ethyl-2- [1- (5-nitrof urfurylidenamino) -
2,4-dioxo-3-imidazolidyl] -ethylcarbamat, som har følgende formel
Det er blitt funnet at den nye forbindelse har keunoterapøytisk virkning og
kan anvendes mot stafylokokinfeksjoner i
systemet ved oral administrasjon på dyr.
Forbindelsen er relativt ugiftig, hvorun-der mus tåler en dose såpass stor som
2200 mg/kg uten å skades. Mus som er
dødelig infisert med Staphylococcus au-reus, blir beskyttet når de får en dose av
forbindelsen som er langt mindre enn en
giftig dose. En eneste dose på 210 mg/kg,
som administreres oralt en halv time efter infeksjonen, beskytter 70 pst. av musene. En dose på 70 mg/kg, som administreres i/2, 4 eller 8 timer efter infeksjonen, beskytter 80 pst. av musene.
Forbindelsen lar seg lett overføre til
et preparat ved hjelp av fyllstoffer og bæ-rere, som ikke er forenbare med den, for
dannelse av tabletter, suspensjoner, elexi-rer, pastiller og lignende.
Fremgangsmåten ifølge oppfinnelsen
består i at man bringer natrium-l-benzyl-
idenaminohydantoin til å reagere med 2-klorethylurethan under innvirkning av varme i nærvær av et organisk oppløs-ningsmiddel, f. eks. dimethylformamid. Oppløsningsmidlet fjernes under forminsket trykk, og resten omdestilleres i sur-gjort vandig medium. Oppløsningen behandles derefter med 5-nitro-2-furalde-hyd eller et reaksjonsdyktig derivat derav, som er i stand til å hydrolyseres til denne, i reaksjonsmediet for dannelse av det ønskede sluttprodukt.
Eksempel.
Til en oppløsning av 51 g (0,25 mol) 1-benzylidenaminohydantoin i 1250 ml dimethylformamid tilsettes 11,0 g (0,25 mol) 55-prosents natriumhydrid i mineralolje. Når hydridet har reagert, tilsettes 38,5 g
(0,26 mol) 2-klorethylurethan [Anm. 566: 239 (1950)], og blandingen oppvarmes til 105—110° C i løpet av natten. Efter kjø-
ling filtreres saltet og dimethylformamid-oppløsningen inndampes til tørrhet under
forminsket trykk. Resten omdestilleres i
nærvær av fortynnet svovelsyre. Den van-dige oppløsning behandles med trekull,
filtreres og bringes til å reagere med en
oppløsning av 0,35 g 5-nitro-2-furaldehyd
i alkohol. Det rå ethyl-2-[l-(5-nitrofurfu-rylidenamino) -2,4-dioxo-3-imidazolidyl] -
ethylcarbamat filtreres, vaskes med vann,
alkohol og eter og tørkes ved 110° C. Det
fåes 59 g (67 pst.) råprodukt av ethyl-2-[1- (5-nitrof urfurylidenamino) -2,4-dioxo-
3-imidazolidyl]-ethylcarbamat. To omkry-stalliseringer fra 100 ml nitromethan under anvendelse av trekull gir 46 g rent produkt, som smelter ved 176—177° C.
Claims (1)
- Fremgangsmåte for fremstilling av det terapeutisk virksomme etyl-2-[l-(5-nitrofurfurylidenamino)-2,4-dioxo-3-imidazol]-ethylcarbamat, som har forme-lenkarakterisert ved at man bringer et alkalisalt av 1-benzylidenaminohydantoin til å reagere med 2-klorethylurethan i nærvær av et, inert fortynningsmiddel, og deretter behandler reaksjonsproduktet med 5-nitro-2-furaldehyd eller et derivat derav som er istand til å hydrolyseres til dette.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB46214/75A GB1564400A (en) | 1975-11-07 | 1975-11-07 | Proteinaceous low fat spread |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO763782L NO763782L (no) | 1977-05-10 |
| NO142646B true NO142646B (no) | 1980-06-16 |
| NO142646C NO142646C (no) | 1980-09-24 |
Family
ID=10440326
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO763782A NO142646C (no) | 1975-11-07 | 1976-11-08 | Fremgangsmaate for fremstilling av et smoerbart naeringsmiddel med lavt fettinnhold av vann-i-oljetype |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US4071634A (no) |
| JP (1) | JPS609772B2 (no) |
| AT (1) | AT348315B (no) |
| AU (1) | AU503127B2 (no) |
| BE (1) | BE848066A (no) |
| CA (1) | CA1083406A (no) |
| CH (1) | CH620343A5 (no) |
| DE (1) | DE2650980C2 (no) |
| FR (1) | FR2330325A1 (no) |
| GB (1) | GB1564400A (no) |
| IE (1) | IE43808B1 (no) |
| IT (1) | IT1108451B (no) |
| LU (1) | LU76138A1 (no) |
| NL (1) | NL7612220A (no) |
| NO (1) | NO142646C (no) |
| SE (1) | SE425045C (no) |
| ZA (1) | ZA766638B (no) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4238520A (en) * | 1979-06-28 | 1980-12-09 | Scm Corporation | Low-fat comestible spread substitutes |
| US4307125A (en) * | 1979-12-26 | 1981-12-22 | Gay-Lea Foods Co-Operative Limited | Low fat butter-like spread |
| NL8002925A (nl) * | 1980-05-21 | 1981-12-16 | Unilever Nv | Werkwijze ter bereiding van vetarme olie-in-water-in-olie emulsies. |
| DE3264362D1 (en) * | 1981-02-27 | 1985-08-01 | Unilever Nv | A process for producing a spreadable emulsion |
| EP0076549B1 (en) * | 1981-10-07 | 1985-03-27 | Unilever N.V. | Low-fat spread and process for producing same |
| US4551346A (en) * | 1981-11-11 | 1985-11-05 | Alpen Dairy Foods Pty. Limited | Method of producing an edible fat emulsion and food product produced thereof |
| JPS58501893A (ja) * | 1981-11-11 | 1983-11-10 | アルペン デイリイ フ−ズ プロプライエタリイ リミテツド | 食品の製造方法とその方法により製造される食品 |
| FI832413L (fi) * | 1982-07-08 | 1984-01-09 | Unilever Nv | Reducerad fettbredning och foerfarande foer dess framstaellning |
| DE3370124D1 (en) * | 1982-07-08 | 1987-04-16 | Unilever Nv | Process for the production of a reduced fat spread |
| GB2130233B (en) * | 1982-11-22 | 1986-10-01 | Unilever Plc | Spread having butter-like properties |
| JPH0789867B2 (ja) * | 1984-04-09 | 1995-10-04 | ミヨシ油脂株式会社 | チーズ様スプレッド食品及びその製造方法 |
| JPH069461B2 (ja) * | 1984-09-19 | 1994-02-09 | 雪印乳業株式会社 | 油中水中油型油脂組成物 |
| US4917915A (en) * | 1986-03-06 | 1990-04-17 | Lever Brothers Company | Water-in-oil emulsion spread |
| GB2205849B (en) * | 1987-06-19 | 1991-05-15 | Brinkers Margarinefab | Low fat spread and process for producing same |
| GB8725803D0 (en) * | 1987-11-04 | 1987-12-09 | Unilever Plc | Preparing edible dispersion |
| DE3869948D1 (de) * | 1988-02-18 | 1992-05-14 | Unilever Nv | Hitzesterilisierbare wasser-und-oel-emulsion. |
| JPH0824534B2 (ja) * | 1992-03-02 | 1996-03-13 | カンバーランド・パツキング・コーポレーシヨン | 天然バターの風味をもつマーガリン等のスプレッドの製造方法 |
| US7368143B2 (en) * | 2003-08-22 | 2008-05-06 | Cumberland Packing Corporation | Low-calorie low-fat butter-flavored topping compositions and methods of preparation |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2575874A (en) * | 1941-09-15 | 1951-11-20 | Grindstedvaerket As | Production of oil-in-oil emulsions |
| GB1029552A (en) * | 1962-03-23 | 1966-05-11 | Unilever Ltd | Fatty composition |
| DE1442001C3 (de) * | 1962-06-15 | 1978-08-31 | Asahi Denka Kogyo K.K., Tokio | Eßbare plastische Margarine |
| US3360377A (en) * | 1964-04-10 | 1967-12-26 | Spitzer Joseph George | Method for production of low-calorie margarine substitute products |
| US3360378A (en) * | 1967-07-12 | 1967-12-26 | Spitzer Joseph George | Low calorie margarine substitute product |
| LU55012A1 (no) * | 1967-12-04 | 1969-08-04 | ||
| US3519436A (en) * | 1969-05-09 | 1970-07-07 | Grace W R & Co | Method for making plastic low fat emulsion spread |
| LU60482A1 (no) * | 1970-03-09 | 1970-05-11 | ||
| DD99087A1 (no) * | 1972-01-17 | 1973-07-20 | ||
| JPS5533294B2 (no) * | 1972-07-21 | 1980-08-29 |
-
1975
- 1975-11-07 GB GB46214/75A patent/GB1564400A/en not_active Expired
-
1976
- 1976-11-02 US US05/737,926 patent/US4071634A/en not_active Expired - Lifetime
- 1976-11-04 NL NL7612220A patent/NL7612220A/xx not_active Application Discontinuation
- 1976-11-05 BE BE172144A patent/BE848066A/xx not_active IP Right Cessation
- 1976-11-05 LU LU76138A patent/LU76138A1/xx unknown
- 1976-11-05 SE SE7612403A patent/SE425045C/xx not_active IP Right Cessation
- 1976-11-05 AU AU19346/76A patent/AU503127B2/en not_active Expired
- 1976-11-05 ZA ZA00766638A patent/ZA766638B/xx unknown
- 1976-11-05 FR FR7633458A patent/FR2330325A1/fr active Granted
- 1976-11-08 AT AT826876A patent/AT348315B/de not_active IP Right Cessation
- 1976-11-08 JP JP51134023A patent/JPS609772B2/ja not_active Expired
- 1976-11-08 IE IE2471/76A patent/IE43808B1/en unknown
- 1976-11-08 NO NO763782A patent/NO142646C/no unknown
- 1976-11-08 IT IT69669/76A patent/IT1108451B/it active
- 1976-11-08 CH CH1404876A patent/CH620343A5/de not_active IP Right Cessation
- 1976-11-08 CA CA265,129A patent/CA1083406A/en not_active Expired
- 1976-11-08 DE DE2650980A patent/DE2650980C2/de not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE2650980A1 (de) | 1977-05-18 |
| CA1083406A (en) | 1980-08-12 |
| FR2330325B1 (no) | 1982-01-22 |
| JPS609772B2 (ja) | 1985-03-13 |
| JPS5258706A (en) | 1977-05-14 |
| IT1108451B (it) | 1985-12-09 |
| SE425045C (sv) | 1984-07-16 |
| SE425045B (sv) | 1982-08-30 |
| NO142646C (no) | 1980-09-24 |
| NL7612220A (nl) | 1977-05-10 |
| LU76138A1 (no) | 1977-06-02 |
| AU503127B2 (en) | 1979-08-23 |
| GB1564400A (en) | 1980-04-10 |
| ZA766638B (en) | 1978-06-28 |
| IE43808B1 (en) | 1981-06-03 |
| ATA826876A (de) | 1978-06-15 |
| DE2650980C2 (de) | 1983-01-27 |
| SE7612403L (sv) | 1977-05-08 |
| IE43808L (en) | 1977-05-07 |
| CH620343A5 (no) | 1980-11-28 |
| BE848066A (fr) | 1977-05-05 |
| US4071634A (en) | 1978-01-31 |
| FR2330325A1 (fr) | 1977-06-03 |
| AU1934676A (en) | 1978-05-11 |
| NO763782L (no) | 1977-05-10 |
| AT348315B (de) | 1979-02-12 |
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