IE35532L - Nitrofuran and nitrothiophene derivatives - Google Patents
Nitrofuran and nitrothiophene derivativesInfo
- Publication number
- IE35532L IE35532L IE78271A IE78271A IE35532L IE 35532 L IE35532 L IE 35532L IE 78271 A IE78271 A IE 78271A IE 78271 A IE78271 A IE 78271A IE 35532 L IE35532 L IE 35532L
- Authority
- IE
- Ireland
- Prior art keywords
- alkyl
- compound
- formula
- radical
- atom
- Prior art date
Links
- JIZRGGUCOQKGQD-UHFFFAOYSA-N 2-nitrothiophene Chemical class [O-][N+](=O)C1=CC=CS1 JIZRGGUCOQKGQD-UHFFFAOYSA-N 0.000 title abstract 2
- IAIWVQXQOWNYOU-FPYGCLRLSA-N nitrofural Chemical compound NC(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 IAIWVQXQOWNYOU-FPYGCLRLSA-N 0.000 title abstract 2
- 229960001907 nitrofurazone Drugs 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 8
- 229910052757 nitrogen Inorganic materials 0.000 abstract 5
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 5
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 3
- 229910052760 oxygen Inorganic materials 0.000 abstract 3
- 150000003839 salts Chemical class 0.000 abstract 3
- HSFWRNGVRCDJHI-UHFFFAOYSA-N Acetylene Chemical compound C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 abstract 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 2
- 229910052799 carbon Inorganic materials 0.000 abstract 2
- 230000005494 condensation Effects 0.000 abstract 2
- 238000009833 condensation Methods 0.000 abstract 2
- 125000005842 heteroatom Chemical group 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 239000001301 oxygen Substances 0.000 abstract 2
- 125000002373 5 membered heterocyclic group Chemical group 0.000 abstract 1
- SXINBFXPADXIEY-UHFFFAOYSA-N 5-Nitrofurfural Chemical compound [O-][N+](=O)C1=CC=C(C=O)O1 SXINBFXPADXIEY-UHFFFAOYSA-N 0.000 abstract 1
- CHTSWZNXEKOLPM-UHFFFAOYSA-N 5-nitrothiophene-2-carbaldehyde Chemical compound [O-][N+](=O)C1=CC=C(C=O)S1 CHTSWZNXEKOLPM-UHFFFAOYSA-N 0.000 abstract 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 abstract 1
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 abstract 1
- 239000005864 Sulphur Substances 0.000 abstract 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 abstract 1
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 230000000845 anti-microbial effect Effects 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 abstract 1
- 125000002619 bicyclic group Chemical group 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 238000006396 nitration reaction Methods 0.000 abstract 1
- 238000007911 parenteral administration Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 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 abstract 1
- 238000011200 topical administration Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
1318013 Nitro-furan and -thiophene derivatives BOEHRINGER MANNHEIM GmbH 16 June 1971 [19 June 1970 1 March 1971 (2)] 28216/71 Heading C2C Novel compounds of Formula I: wherein Het signifies a divalent radical of aromatic character, optionally substituted by halogen atoms, hydroxyl, azido or cyano groups or alkyl, alkoxy, alkylthio or alkylamino radicals, and is either (i) a five-membered ring containing two or three heteroatoms, at least one of which is a nitrogen atom, or (ii) a sixmembered ring containing 1-3 nitrogen atoms, or (iii) a bicyclic ring in which two of the rings according to (i) and/or (ii) are fused together in such a manner that they contain a nitrogen atom which is common to both rings, B being attached to the α-position in respect to a nitrogen atom in the Het radical and the righthand side of the molecule being attached to another carbon atom in the Het radical; Y is an oxygen or sulphur atom; m is 0 or 1, X is a hydrogen atom or a C 1 -C 6 alkyl or C 1 -C 6 acyl radical; B is a valency bond or, when m is 1, can also be a vinylene radical; R is a hydrogen atom or a C 1 -C 6 alkyl or alkoxyalkyl radical and R 1 and R 2 , which can be the same or different, are hydrogen atoms or hydroxyl groups or C 1 -C 6 alkyl, alkoxyalkyl, C 1 -C 6 hydroxyalkyl, mono-(C 1 -C 6 alkyl)-amino or di(C 1 -C 6 alkyl)-amino radicals or optionally substituted aryl- or aralkyl radicals or wherein two of the symbols R, R 1 and R 2 , together with the nitrogen atom to which R 1 and R 2 are attached, form a saturated 5- or 6-membered heterocyclic ring, which can optionally contain one or two additional hetero atoms, such as oxygen, sulphur or nitrogen; and the physiologically compatible acid-addition salts thereof, are prepared by (a) condensation of a compound of Formula II: with a compound of Formula III: in which Z is O or S, or a ketal or acetal thereof, or with a compound of formula R 1 -N= C(R)-Z-R 5 or RCN wherein R 5 is alkyl, or (b) reaction of a compound of Formula IV: in which R 3 is C 1-6 alkyl and R 4 is H or C 1-6 alkyl, or a salt thereof, with a compound of formula R 1 -NH-R 2 , or (c) nitration of a compound of Formula V: or (d) when B represents a vinylene radical, condensation of 5-nitrofuran-2-aldehyde or 5-nitrothiophene-2-aldehyde or a reactive derivative thereof, with a compound of Formula VI: Pharmaceutical compositions having antimicrobial activity, for oral, parenteral or topical administration, comprise a compound I or a pharmacologically acceptable acid addition salt thereof, together with a pharmaceutical carrier.
[GB1318013A]
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702030218 DE2030218A1 (en) | 1970-06-19 | 1970-06-19 | Nitrofuryl (or thienyl) antimicrobials -5-substd - by aminomethylene-amino (or hydrazino) heterocyclyl-(vinyl)group |
| DE19712109570 DE2109570A1 (en) | 1971-03-01 | 1971-03-01 | Antimicrobial Nitrofuran Derivatives and Process for the Production of the Same |
| DE19712109577 DE2109577A1 (en) | 1971-03-01 | 1971-03-01 | Antimicrobial Nitrofuran Derivatives and Process for the Production of the Same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE35532L true IE35532L (en) | 1971-12-19 |
| IE35532B1 IE35532B1 (en) | 1976-03-18 |
Family
ID=27182673
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE78271A IE35532B1 (en) | 1970-06-19 | 1971-06-17 | Nitrofuran and nitrothiophene derivatives |
Country Status (6)
| Country | Link |
|---|---|
| CA (1) | CA942303A (en) |
| FR (1) | FR2100787B1 (en) |
| GB (1) | GB1318013A (en) |
| IE (1) | IE35532B1 (en) |
| NL (1) | NL7108313A (en) |
| SE (1) | SE373140B (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2222834A1 (en) * | 1972-05-10 | 1973-11-29 | Boehringer Mannheim Gmbh | NITROFURYL AMIDINE DERIVATIVES AND METHOD FOR PREPARING THE SAME |
| GB1324060A (en) * | 1971-03-19 | 1973-07-18 | Boehringer Mannheim Gmbh | Nitrofuryl-triazolo 4,3-b pyridazine derivatives |
| DK185389A (en) * | 1988-04-22 | 1989-10-23 | Duphar Int Res | 3,5-SUBSTITUTED 1,2,4-OXADIAZOLES, THEIR PREPARATION AND USE |
| FR2668151A1 (en) * | 1990-10-23 | 1992-04-24 | Rhone Poulenc Agrochimie | TRIAZOLOPYRIDAZINE GROUP COMPOUNDS THEIR PREPARATIONS AND HERBICIDAL COMPOSITIONS CONTAINING SAME. |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2027503A1 (en) * | 1969-01-06 | 1970-10-02 | Toyama Chemical Co Ltd | Nitrofurane derivs for chemotherapeutic - applications |
-
1971
- 1971-06-16 GB GB2821671A patent/GB1318013A/en not_active Expired
- 1971-06-17 NL NL7108313A patent/NL7108313A/xx unknown
- 1971-06-17 IE IE78271A patent/IE35532B1/en unknown
- 1971-06-17 FR FR7121966A patent/FR2100787B1/fr not_active Expired
- 1971-06-17 SE SE787171A patent/SE373140B/xx unknown
- 1971-06-18 CA CA116,102A patent/CA942303A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2100787B1 (en) | 1975-06-06 |
| FR2100787A1 (en) | 1972-03-24 |
| GB1318013A (en) | 1973-05-23 |
| IE35532B1 (en) | 1976-03-18 |
| NL7108313A (en) | 1971-12-21 |
| CA942303A (en) | 1974-02-19 |
| SE373140B (en) | 1975-01-27 |
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