IL31286A - 5-nitro-2-furfurylideneaminooxazolidinone compounds and their preparation - Google Patents
5-nitro-2-furfurylideneaminooxazolidinone compounds and their preparationInfo
- Publication number
- IL31286A IL31286A IL31286A IL3128668A IL31286A IL 31286 A IL31286 A IL 31286A IL 31286 A IL31286 A IL 31286A IL 3128668 A IL3128668 A IL 3128668A IL 31286 A IL31286 A IL 31286A
- Authority
- IL
- Israel
- Prior art keywords
- oxazolidinone
- nitro
- nitrofurfurylideneamino
- furfurylideneamino
- group
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 20
- 238000002360 preparation method Methods 0.000 title description 3
- 238000000034 method Methods 0.000 claims description 43
- -1 oxazolidinone compound Chemical class 0.000 claims description 35
- 239000000203 mixture Substances 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 239000007787 solid Substances 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 6
- 150000008064 anhydrides Chemical class 0.000 claims description 5
- 238000006396 nitration reaction Methods 0.000 claims description 5
- 239000011368 organic material Substances 0.000 claims description 5
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 230000001580 bacterial effect Effects 0.000 claims description 4
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 4
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 3
- RLWGDBRCIKPLFY-UHFFFAOYSA-N C(C=CC)(=O)OCC1CN(C(O1)=O)N=CC1=CC=C(O1)[N+](=O)[O-] Chemical compound C(C=CC)(=O)OCC1CN(C(O1)=O)N=CC1=CC=C(O1)[N+](=O)[O-] RLWGDBRCIKPLFY-UHFFFAOYSA-N 0.000 claims description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical group 0.000 claims description 3
- 230000000813 microbial effect Effects 0.000 claims description 3
- 230000000802 nitrating effect Effects 0.000 claims description 3
- CROMCJZTBAFPFA-UHFFFAOYSA-N C(CCCCC)(=O)OCC1CN(C(O1)=O)N=CC1=CC=C(O1)[N+](=O)[O-] Chemical compound C(CCCCC)(=O)OCC1CN(C(O1)=O)N=CC1=CC=C(O1)[N+](=O)[O-] CROMCJZTBAFPFA-UHFFFAOYSA-N 0.000 claims description 2
- WYMJQVVUNNJICX-UHFFFAOYSA-N C(CCCCCCCCC)(=O)OCC1CN(C(O1)=O)N=CC1=CC=C(O1)[N+](=O)[O-] Chemical compound C(CCCCCCCCC)(=O)OCC1CN(C(O1)=O)N=CC1=CC=C(O1)[N+](=O)[O-] WYMJQVVUNNJICX-UHFFFAOYSA-N 0.000 claims description 2
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- QSFSEFMSYWLSCA-UHFFFAOYSA-N [3-[(5-nitrofuran-2-yl)methylideneamino]-2-oxo-1,3-oxazolidin-5-yl]methyl 2-methoxyacetate Chemical compound COCC(=O)OCC1CN(C(O1)=O)N=CC1=CC=C(O1)[N+](=O)[O-] QSFSEFMSYWLSCA-UHFFFAOYSA-N 0.000 claims description 2
- XJCILULZNCQSNO-UHFFFAOYSA-N [3-[(5-nitrofuran-2-yl)methylideneamino]-2-oxo-1,3-oxazolidin-5-yl]methyl 2-methylpropanoate Chemical compound C(C(C)C)(=O)OCC1CN(C(O1)=O)N=CC1=CC=C(O1)[N+](=O)[O-] XJCILULZNCQSNO-UHFFFAOYSA-N 0.000 claims description 2
- IVZCCWHFMOGIOK-UHFFFAOYSA-N [3-[(5-nitrofuran-2-yl)methylideneamino]-2-oxo-1,3-oxazolidin-5-yl]methyl acetate Chemical compound C(C)(=O)OCC1CN(C(O1)=O)N=CC1=CC=C(O1)[N+](=O)[O-] IVZCCWHFMOGIOK-UHFFFAOYSA-N 0.000 claims description 2
- IDIVTOCFFURUAD-UHFFFAOYSA-N [3-[(5-nitrofuran-2-yl)methylideneamino]-2-oxo-1,3-oxazolidin-5-yl]methyl butanoate Chemical compound C(CCC)(=O)OCC1CN(C(O1)=O)N=CC1=CC=C(O1)[N+](=O)[O-] IDIVTOCFFURUAD-UHFFFAOYSA-N 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 239000012024 dehydrating agents Substances 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
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- 239000000376 reactant Substances 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims description 2
- VBJWRJBIIWTOOP-UHFFFAOYSA-N [3-[(5-nitrofuran-2-yl)methylideneamino]-2-oxo-1,3-oxazolidin-5-yl]methyl formate Chemical compound C(=O)OCC1CN(C(O1)=O)N=CC1=CC=C(O1)[N+](=O)[O-] VBJWRJBIIWTOOP-UHFFFAOYSA-N 0.000 claims 1
- PLHJDBGFXBMTGZ-UHFFFAOYSA-N furazolidone Chemical compound O1C([N+](=O)[O-])=CC=C1C=NN1C(=O)OCC1 PLHJDBGFXBMTGZ-UHFFFAOYSA-N 0.000 claims 1
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- 239000000047 product Substances 0.000 description 37
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- 238000006243 chemical reaction Methods 0.000 description 24
- 238000002844 melting Methods 0.000 description 20
- 230000008018 melting Effects 0.000 description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- 238000001953 recrystallisation Methods 0.000 description 7
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- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- LSACYLWPPQLVSM-UHFFFAOYSA-N isobutyric acid anhydride Chemical compound CC(C)C(=O)OC(=O)C(C)C LSACYLWPPQLVSM-UHFFFAOYSA-N 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- UJQMLHKSZKBMMO-UHFFFAOYSA-N n,n-diethylethanamine;pyridine Chemical compound C1=CC=NC=C1.CCN(CC)CC UJQMLHKSZKBMMO-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 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
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 150000007530 organic bases Chemical group 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical class C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 229940100486 rice starch Drugs 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 208000017520 skin disease Diseases 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000001420 substituted heterocyclic compounds Chemical class 0.000 description 1
- 229960004793 sucrose Drugs 0.000 description 1
- 239000007940 sugar coated tablet Substances 0.000 description 1
- 229960000654 sulfafurazole Drugs 0.000 description 1
- 229960002597 sulfamerazine Drugs 0.000 description 1
- QPPBRPIAZZHUNT-UHFFFAOYSA-N sulfamerazine Chemical compound CC1=CC=NC(NS(=O)(=O)C=2C=CC(N)=CC=2)=N1 QPPBRPIAZZHUNT-UHFFFAOYSA-N 0.000 description 1
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical class NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 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 description 1
- 229960002180 tetracycline Drugs 0.000 description 1
- 229930101283 tetracycline Natural products 0.000 description 1
- 235000019364 tetracycline Nutrition 0.000 description 1
- 150000003522 tetracyclines Chemical class 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- KVSKGMLNBAPGKH-UHFFFAOYSA-N tribromosalicylanilide Chemical compound OC1=C(Br)C=C(Br)C=C1C(=O)NC1=CC=C(Br)C=C1 KVSKGMLNBAPGKH-UHFFFAOYSA-N 0.000 description 1
- 230000000654 trypanocidal effect Effects 0.000 description 1
- 210000001635 urinary tract Anatomy 0.000 description 1
- 208000019206 urinary tract infection Diseases 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- A61K31/42—Oxazoles
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB57585/67A GB1199205A (en) | 1967-12-19 | 1967-12-19 | 5-Nitro-2-Furfurylideneamino-Oxazolidines |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL31286A0 IL31286A0 (en) | 1969-02-27 |
| IL31286A true IL31286A (en) | 1972-06-28 |
Family
ID=10479535
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL31286A IL31286A (en) | 1967-12-19 | 1968-12-18 | 5-nitro-2-furfurylideneaminooxazolidinone compounds and their preparation |
Country Status (19)
| Country | Link |
|---|---|
| AT (1) | AT281805B (de) |
| BE (1) | BE725657A (de) |
| BG (2) | BG15032A3 (de) |
| BR (1) | BR6804960D0 (de) |
| CA (1) | CA956629A (de) |
| CH (1) | CH507282A (de) |
| CS (2) | CS154601B2 (de) |
| DE (1) | DE1815466A1 (de) |
| DK (1) | DK125396B (de) |
| ES (1) | ES361605A1 (de) |
| FI (1) | FI48841C (de) |
| FR (2) | FR8222M (de) |
| GB (1) | GB1199205A (de) |
| IE (1) | IE32590B1 (de) |
| IL (1) | IL31286A (de) |
| NL (1) | NL147436B (de) |
| NO (1) | NO128442B (de) |
| SE (1) | SE339689B (de) |
| YU (2) | YU32709B (de) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT298504B (de) * | 1969-06-05 | 1972-04-15 | Geigy Ag J R | Verfahren zur herstellung von neuen 5-nitrofurylderivaten |
-
1967
- 1967-12-19 GB GB57585/67A patent/GB1199205A/en not_active Expired
-
1968
- 1968-03-17 FR FR183283A patent/FR8222M/fr not_active Expired
- 1968-11-30 CH CH1785968A patent/CH507282A/de not_active IP Right Cessation
- 1968-12-12 DK DK607868AA patent/DK125396B/da unknown
- 1968-12-12 FI FI683557A patent/FI48841C/fi active
- 1968-12-12 NO NO04980/68A patent/NO128442B/no unknown
- 1968-12-12 NL NL686817857A patent/NL147436B/xx unknown
- 1968-12-12 SE SE17016/68A patent/SE339689B/xx unknown
- 1968-12-17 YU YU2981/68A patent/YU32709B/xx unknown
- 1968-12-18 BR BR204960/68A patent/BR6804960D0/pt unknown
- 1968-12-18 BG BG011262A patent/BG15032A3/bg unknown
- 1968-12-18 ES ES361605A patent/ES361605A1/es not_active Expired
- 1968-12-18 FR FR1597906D patent/FR1597906A/fr not_active Expired
- 1968-12-18 BE BE725657D patent/BE725657A/xx unknown
- 1968-12-18 CA CA038,130A patent/CA956629A/en not_active Expired
- 1968-12-18 AT AT1230568A patent/AT281805B/de not_active IP Right Cessation
- 1968-12-18 CS CS858768A patent/CS154601B2/cs unknown
- 1968-12-18 IE IE1528/68A patent/IE32590B1/xx unknown
- 1968-12-18 IL IL31286A patent/IL31286A/en unknown
- 1968-12-18 DE DE19681815466 patent/DE1815466A1/de active Pending
- 1968-12-18 CS CS359872*1A patent/CS154602B2/cs unknown
- 1968-12-18 BG BG012968A patent/BG15223A3/bg unknown
-
1973
- 1973-05-17 YU YU1311/73A patent/YU33073B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE1815466A1 (de) | 1969-07-24 |
| ES361605A1 (es) | 1971-06-16 |
| CS154602B2 (de) | 1974-04-30 |
| BE725657A (de) | 1969-06-18 |
| CA956629A (en) | 1974-10-22 |
| BG15032A3 (bg) | 1975-06-15 |
| CH507282A (de) | 1971-05-15 |
| YU32709B (en) | 1975-06-30 |
| IE32590B1 (en) | 1973-09-19 |
| FI48841B (de) | 1974-09-30 |
| IL31286A0 (en) | 1969-02-27 |
| FI48841C (fi) | 1975-01-10 |
| NL6817857A (de) | 1969-06-23 |
| AT281805B (de) | 1970-06-10 |
| IE32590L (en) | 1969-06-19 |
| DK125396B (da) | 1973-02-12 |
| BG15223A3 (bg) | 1971-11-27 |
| YU298168A (en) | 1974-12-31 |
| NO128442B (de) | 1973-11-19 |
| CS154601B2 (de) | 1974-04-30 |
| YU33073B (en) | 1976-03-31 |
| FR1597906A (de) | 1970-06-29 |
| NL147436B (nl) | 1975-10-15 |
| YU131173A (en) | 1975-08-31 |
| BR6804960D0 (pt) | 1973-02-08 |
| GB1199205A (en) | 1970-07-15 |
| SE339689B (de) | 1971-10-18 |
| FR8222M (de) | 1970-09-21 |
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