DE1770806A1 - Nitrofuranderivate und Verfahren zu deren Herstellung - Google Patents
Nitrofuranderivate und Verfahren zu deren HerstellungInfo
- Publication number
- DE1770806A1 DE1770806A1 DE19681770806 DE1770806A DE1770806A1 DE 1770806 A1 DE1770806 A1 DE 1770806A1 DE 19681770806 DE19681770806 DE 19681770806 DE 1770806 A DE1770806 A DE 1770806A DE 1770806 A1 DE1770806 A1 DE 1770806A1
- Authority
- DE
- Germany
- Prior art keywords
- compounds
- formula
- hydrogen
- alk
- methyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 4
- 229940027988 antiseptic and disinfectant nitrofuran derivative Drugs 0.000 title description 4
- IAIWVQXQOWNYOU-FPYGCLRLSA-N nitrofural Chemical class NC(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 IAIWVQXQOWNYOU-FPYGCLRLSA-N 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims description 18
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 150000002431 hydrogen Chemical group 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 230000000844 anti-bacterial effect Effects 0.000 claims description 4
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 230000003385 bacteriostatic effect Effects 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 238000007363 ring formation reaction Methods 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 208000027954 Poultry disease Diseases 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 238000005580 one pot reaction Methods 0.000 claims description 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 2
- 230000001580 bacterial effect Effects 0.000 claims 1
- 238000011321 prophylaxis Methods 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- -1 5-Nitrofurfurylidene Chemical group 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- NDSTUUPEXNCUNW-UHFFFAOYSA-N (5-nitrofuran-2-yl)methanol Chemical compound OCC1=CC=C([N+]([O-])=O)O1 NDSTUUPEXNCUNW-UHFFFAOYSA-N 0.000 description 2
- HQDAJGNZGNZGCO-UHFFFAOYSA-N (propan-2-ylideneamino)urea Chemical compound CC(C)=NNC(N)=O HQDAJGNZGNZGCO-UHFFFAOYSA-N 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 241000607142 Salmonella Species 0.000 description 2
- 206010039438 Salmonella Infections Diseases 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 206010039447 salmonellosis Diseases 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- HJKLEAOXCZIMPI-UHFFFAOYSA-N 2,2-diethoxyethanamine Chemical compound CCOC(CN)OCC HJKLEAOXCZIMPI-UHFFFAOYSA-N 0.000 description 1
- LYIIBVSRGJSHAV-UHFFFAOYSA-N 2-aminoacetaldehyde Chemical class NCC=O LYIIBVSRGJSHAV-UHFFFAOYSA-N 0.000 description 1
- SXINBFXPADXIEY-UHFFFAOYSA-N 5-Nitrofurfural Chemical class [O-][N+](=O)C1=CC=C(C=O)O1 SXINBFXPADXIEY-UHFFFAOYSA-N 0.000 description 1
- ZETHHMPKDUSZQQ-UHFFFAOYSA-N Betulafolienepentol Natural products C1C=C(C)CCC(C(C)CCC=C(C)C)C2C(OC)OC(OC)C2=C1 ZETHHMPKDUSZQQ-UHFFFAOYSA-N 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 241000588767 Proteus vulgaris Species 0.000 description 1
- 241000607132 Salmonella enterica subsp. enterica serovar Gallinarum Species 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- 241000193996 Streptococcus pyogenes Species 0.000 description 1
- PCSMJKASWLYICJ-UHFFFAOYSA-N Succinic aldehyde Chemical compound O=CCCC=O PCSMJKASWLYICJ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- HEOKFDGOFROELJ-UHFFFAOYSA-N diacetal Natural products COc1ccc(C=C/c2cc(O)cc(OC3OC(COC(=O)c4cc(O)c(O)c(O)c4)C(O)C(O)C3O)c2)cc1O HEOKFDGOFROELJ-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- MCSAJNNLRCFZED-UHFFFAOYSA-N nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 244000144977 poultry Species 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 229940007042 proteus vulgaris Drugs 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 150000007659 semicarbazones Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US65201567A | 1967-07-10 | 1967-07-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1770806A1 true DE1770806A1 (de) | 1972-01-13 |
Family
ID=24615173
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19681770806 Pending DE1770806A1 (de) | 1967-07-10 | 1968-07-05 | Nitrofuranderivate und Verfahren zu deren Herstellung |
Country Status (10)
| Country | Link |
|---|---|
| AT (1) | AT277986B (https=) |
| BE (1) | BE717607A (https=) |
| CH (1) | CH495375A (https=) |
| DE (1) | DE1770806A1 (https=) |
| DK (1) | DK115919B (https=) |
| ES (1) | ES355759A1 (https=) |
| FR (1) | FR1605405A (https=) |
| GB (1) | GB1167471A (https=) |
| IE (1) | IE32031B1 (https=) |
| NL (1) | NL6809744A (https=) |
-
1968
- 1968-04-08 DK DK156668A patent/DK115919B/da unknown
- 1968-04-23 GB GB1923568A patent/GB1167471A/en not_active Expired
- 1968-04-25 IE IE48268A patent/IE32031B1/xx unknown
- 1968-07-04 ES ES355759A patent/ES355759A1/es not_active Expired
- 1968-07-04 BE BE717607D patent/BE717607A/xx unknown
- 1968-07-05 DE DE19681770806 patent/DE1770806A1/de active Pending
- 1968-07-05 AT AT650568A patent/AT277986B/de not_active IP Right Cessation
- 1968-07-05 CH CH1005268A patent/CH495375A/de not_active IP Right Cessation
- 1968-07-09 FR FR158484A patent/FR1605405A/fr not_active Expired
- 1968-07-10 NL NL6809744A patent/NL6809744A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES355759A1 (es) | 1969-12-16 |
| IE32031L (en) | 1969-01-10 |
| GB1167471A (en) | 1969-10-15 |
| NL6809744A (https=) | 1969-01-14 |
| DK115919B (da) | 1969-11-24 |
| FR1605405A (en) | 1975-04-18 |
| BE717607A (https=) | 1968-12-16 |
| AT277986B (de) | 1970-01-12 |
| CH495375A (de) | 1970-08-31 |
| IE32031B1 (en) | 1973-03-21 |
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