NO115956B - - Google Patents
Info
- Publication number
- NO115956B NO115956B NO1656I4*[A NO16566666A NO115956B NO 115956 B NO115956 B NO 115956B NO 16566666 A NO16566666 A NO 16566666A NO 115956 B NO115956 B NO 115956B
- Authority
- NO
- Norway
- Prior art keywords
- compound
- hydroxymethyl
- nitro
- nitrofurfurylideneamino
- formula
- Prior art date
Links
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 5
- 230000000844 anti-bacterial effect Effects 0.000 claims description 4
- 238000001228 spectrum Methods 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 description 12
- 241000287828 Gallus gallus Species 0.000 description 2
- 241000607142 Salmonella Species 0.000 description 2
- 239000002246 antineoplastic agent Substances 0.000 description 2
- 235000013330 chicken meat Nutrition 0.000 description 2
- 229940127089 cytotoxic agent Drugs 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 1
- 241000223932 Eimeria tenella Species 0.000 description 1
- 241000186811 Erysipelothrix Species 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- VSVAVMVWTLLTCH-BJMVGYQFSA-N Nifuradene Chemical compound O1C([N+](=O)[O-])=CC=C1\C=N\N1C(=O)NCC1 VSVAVMVWTLLTCH-BJMVGYQFSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 241000194017 Streptococcus Species 0.000 description 1
- 241000193985 Streptococcus agalactiae Species 0.000 description 1
- 241000187747 Streptomyces Species 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000004071 soot Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 208000019206 urinary tract infection Diseases 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
-
- 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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Inking, Control Or Cleaning Of Printing Machines (AREA)
Description
Fremgangsmåte for fremstilling av l-hydroksymetyl-3(5-rritro-furfuryli-denamino)-2-imidazolidinon med bredt antibakterielt-spektrum.
Oppfinnelsen vedrflrer en fremgangsmåte for fremstilling a^dssn hittil ei:jente forbindelse l~hydrok8y-metyl-3- (5-nitro-furfurylidGn~ftE£inoi-g-»icid«afi)lidinon ned formel
Freiagangj$£§«rø» ifdlgo oppfinnelsen erkarakterisert ved£8 Ii^^i^«r^!^iW7li^B£Éino)-2--imidaaolidinon med formel omsettes med vannholdig formaldehyd. Omsetningen foregår fortrinevio under innvirkning av varme.
Den ved fremgangsmåten ifølge oppfinnelsen fremstilte forbindelse utmerker seg ved lav giftighet og er et kjemoterapeutisk kraftig virkende middel ved oral administrering. Den er skadelig for et stort antall parasitter. Forbindelsen har et bredt antibakterielt spektrum, idet den hemmer tilveksten av organismer som f.eks. Staphylo-oocous aureua, Escherichia coli, Streptococcus agalactiae, Erysipe-lothrix inaidosa og Aerobaoter aerogenes i meget små mengder av størrel-sesorden fra 0,31 til 1,5 mg-prosent. Den kan således anvendes som aktiv komponent i middel; beregnet til å utrydde bakterier. Den kan lett kombineres til pulver, besprøytningsvæsker, salver eller liknende farmasøytisk preparat.
Likeledes er forbindelsen et effektivt systemisk kjemoterapeutisk middel. Fremgangsmåteproduktet er prdvet med hensyn på effekt mot infeksjoner fremkalt av Streptomyces auraus og Salmonella typhosa. Herved ble forbindelsene inngitt peroralt i form av en eneste dose på mus som er blitt dødelig infisert med de to mikroorganismer. Mens den nye forbindelses virkning på infeksjoner av Streptococcus aurous sammenliknet med forbindelsen N-(5-nitro-2-furfuryliden)-l-amino-2-imidazolidon ikke skiller seg så meget, oppnås som det frem-går av tabellen en betydelig stOrre effektforskjell når det gjelder Salmonella typhosa.
Hvis forbindelsen inngis på kyllinger sot er infisert
med Eimeria tenella, nedsettes dødeligheten. Herved er et kyllingfor inneholdende 0,022 vekt-j6 av forbindelsen meget effektiv*
Forbindelsen fremstilt ifølge oppfinnelsen utmerker seg videre ved motstandskraft mot metabolisk nedbrytning når den inngis på dyr. Hvis den administreres peroralt på rotter i en dosis på 10 mg/kg, utsondres 15 - 35 % herav med urinen og gjør derved denne antibakteri-ell. Forbindelsen er således velegnet for behandling av urinveis-I infeksjoner. Eksempel.
1- hydrokeymetyl- V( 5- nitro- furfurylidensjnino)- 2- iinida«olidinon.
Til 2 liter 5 Jfig vannholdig formaldehyd som koker under refluks settes 60 g (0,267 mol) l-(5-nitro-furfurylidenandno)-2-imid-azolidinon. Blandingen omrSree under tilbakelQp i 5 minutter og filtreres varmt, hvoretter filtratet avkjøles. De utfelte orange-fargede, flate krystaller av l-hydroksymetyl-3-(5-nitrofurfurylidenamino) 2- imidaiolidlnon fraskilles ved filtrering og vaskes med 200 ml 1 $- lg formaldehydoppløsning. Etter tørking ved værelsestemperatur fåes
14,4 g (21 %) av den ovennevnte forbindelse med smeltepunkt 200°C. Beregnet for C^H^N^Cy C 42,52, H 3,97, N 22,04 %
funnet: C 42,41, H 4,17, N 22,14 %.
Claims (1)
- Fremgangsmåte for fremstilling av l-hydroksymetyl-3-(5=nitro-fvurfurylidenamino)-2-imidazolidinon med bredt antibakterielt spektrum og med formelkarakterisert ved at l-(5-nitrofurfurylidenamino)-2-imida-aolidinon med formelomsettes med vannholdig formaldehyd.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US376199A US3386995A (en) | 1964-06-18 | 1964-06-18 | 1-substituted-3-(5-nitrofurfurylidene-amino)-2-imidazolidinones |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO115956B true NO115956B (no) | 1969-01-06 |
Family
ID=23484076
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO155481A NO115661B (no) | 1964-06-18 | 1964-11-06 | |
| NO1656I4*[A NO115956B (no) | 1964-06-18 | 1966-11-17 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO155481A NO115661B (no) | 1964-06-18 | 1964-11-06 |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US3386995A (no) |
| AT (1) | AT248424B (no) |
| BE (1) | BE653421A (no) |
| BR (1) | BR6463882D0 (no) |
| CH (2) | CH466296A (no) |
| DE (1) | DE1470137A1 (no) |
| DK (2) | DK106803C (no) |
| ES (1) | ES304279A1 (no) |
| FR (2) | FR3776M (no) |
| IL (1) | IL22038A (no) |
| NL (1) | NL6411765A (no) |
| NO (2) | NO115661B (no) |
| SE (1) | SE303292B (no) |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2887485A (en) * | 1956-01-06 | 1959-05-19 | Rohm & Haas | New cyclic urea derivatives |
| US3182058A (en) * | 1960-10-31 | 1965-05-04 | Pfizer & Co C | Nitrofuran derivatives |
| NL272959A (no) * | 1960-12-27 | |||
| FR1310188A (no) * | 1960-12-27 | 1963-03-06 | ||
| US3154543A (en) * | 1961-09-18 | 1964-10-27 | Norwich Pharma Co | Preparation of 5-aminofurans |
| US3076805A (en) * | 1962-02-26 | 1963-02-05 | Norwich Pharma Co | New 1-(hydroxy(lower) alkyl)-3-(5-nitrofurfurylideneamino)-2-imidazolidinethiones |
| US3254075A (en) * | 1963-08-28 | 1966-05-31 | Norwich Pharma Co | 1-(2-hydroxyethyl and 2-haloethyl-3-(5-nitrofurfurylideneamino)-2-imidazolidinones |
-
1964
- 1964-06-18 US US376199A patent/US3386995A/en not_active Expired - Lifetime
- 1964-09-02 ES ES0304279A patent/ES304279A1/es not_active Expired
- 1964-09-03 IL IL22038A patent/IL22038A/xx unknown
- 1964-09-22 BE BE653421A patent/BE653421A/xx unknown
- 1964-09-25 SE SE11508/64A patent/SE303292B/xx unknown
- 1964-09-30 DK DK481464AA patent/DK106803C/da active
- 1964-09-30 DK DK231965AA patent/DK105470C/da active
- 1964-10-09 NL NL6411765A patent/NL6411765A/xx unknown
- 1964-10-13 DE DE19641470137 patent/DE1470137A1/de active Pending
- 1964-10-19 CH CH1472268A patent/CH466296A/de unknown
- 1964-10-19 CH CH1353064A patent/CH464940A/de unknown
- 1964-10-23 FR FR992454A patent/FR3776M/fr not_active Expired
- 1964-10-23 FR FR992453A patent/FR1442307A/fr not_active Expired
- 1964-10-30 BR BR163882/64A patent/BR6463882D0/pt unknown
- 1964-11-06 NO NO155481A patent/NO115661B/no unknown
- 1964-11-10 AT AT949864A patent/AT248424B/de active
-
1966
- 1966-11-17 NO NO1656I4*[A patent/NO115956B/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK105470C (da) | 1966-10-03 |
| AT248424B (de) | 1966-07-25 |
| FR1442307A (fr) | 1966-06-17 |
| IL22038A (en) | 1969-06-25 |
| BR6463882D0 (pt) | 1973-08-02 |
| BE653421A (no) | 1965-03-22 |
| NO115661B (no) | 1968-11-11 |
| CH466296A (de) | 1968-12-15 |
| SE303292B (no) | 1968-08-26 |
| FR3776M (fr) | 1965-12-20 |
| NL6411765A (no) | 1965-12-20 |
| DE1470137A1 (de) | 1969-04-17 |
| US3386995A (en) | 1968-06-04 |
| CH464940A (de) | 1968-11-15 |
| DK106803C (da) | 1967-03-20 |
| ES304279A1 (es) | 1964-12-01 |
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