SU509235A3 - Способ получени производныхнитрофурана или нитротиофена - Google Patents
Способ получени производныхнитрофурана или нитротиофенаInfo
- Publication number
- SU509235A3 SU509235A3 SU2018983A SU2018983A SU509235A3 SU 509235 A3 SU509235 A3 SU 509235A3 SU 2018983 A SU2018983 A SU 2018983A SU 2018983 A SU2018983 A SU 2018983A SU 509235 A3 SU509235 A3 SU 509235A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- triazolo
- pyridazine
- formula
- nitro
- group
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 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 claims description 3
- JIZRGGUCOQKGQD-UHFFFAOYSA-N 2-nitrothiophene Chemical compound [O-][N+](=O)C1=CC=CS1 JIZRGGUCOQKGQD-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 229910052717 sulfur Chemical group 0.000 claims description 3
- 238000007796 conventional method Methods 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- UGUHFDPGDQDVGX-UHFFFAOYSA-N 1,2,3-thiadiazole Chemical group C1=CSN=N1 UGUHFDPGDQDVGX-UHFFFAOYSA-N 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 125000005122 aminoalkylamino group Chemical group 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000005429 oxyalkyl group Chemical group 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 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 claims 1
- -1 hydrochloric Chemical class 0.000 description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- KYBLUOVPGCYJIE-UHFFFAOYSA-N 3-(5-nitrothiophen-2-yl)-[1,2,4]triazolo[4,3-b]pyridazin-6-amine Chemical compound N12N=C(N)C=CC2=NN=C1C1=CC=C([N+]([O-])=O)S1 KYBLUOVPGCYJIE-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 238000004611 spectroscopical analysis Methods 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical group CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- CHTSWZNXEKOLPM-UHFFFAOYSA-N 5-nitrothiophene-2-carbaldehyde Chemical compound [O-][N+](=O)C1=CC=C(C=O)S1 CHTSWZNXEKOLPM-UHFFFAOYSA-N 0.000 description 1
- DBROFCFDGIQJSR-UHFFFAOYSA-N 6-chloro-3-(5-nitrothiophen-2-yl)-[1,2,4]triazolo[4,3-b]pyridazine Chemical compound S1C([N+](=O)[O-])=CC=C1C1=NN=C2N1N=C(Cl)C=C2 DBROFCFDGIQJSR-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- BZNJWQYNUWZVBR-UHFFFAOYSA-N Cl(=O)(=O)[P] Chemical compound Cl(=O)(=O)[P] BZNJWQYNUWZVBR-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- WWKDTDDVBJYENE-UHFFFAOYSA-J acetic acid;triacetyloxyplumbyl acetate Chemical compound CC(O)=O.CC(=O)O[Pb](OC(C)=O)(OC(C)=O)OC(C)=O WWKDTDDVBJYENE-UHFFFAOYSA-J 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000006194 liquid suspension Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Classifications
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2153902A DE2153902A1 (de) | 1971-10-29 | 1971-10-29 | Antimikrobiell wirksame nitrofuranderivate und verfahren zur herstellung derselben |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU509235A3 true SU509235A3 (ru) | 1976-03-30 |
Family
ID=5823698
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU2018983A SU509235A3 (ru) | 1971-10-29 | 1974-04-19 | Способ получени производныхнитрофурана или нитротиофена |
| SU2018982A SU511006A3 (ru) | 1971-10-29 | 1974-04-19 | Способ получени производных нитрофурана или нитротиофена |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU2018982A SU511006A3 (ru) | 1971-10-29 | 1974-04-19 | Способ получени производных нитрофурана или нитротиофена |
Country Status (15)
| Country | Link |
|---|---|
| JP (1) | JPS4852769A (enExample) |
| AR (3) | AR197008A1 (enExample) |
| AT (5) | AT320628B (enExample) |
| AU (1) | AU467712B2 (enExample) |
| DD (1) | DD102387A5 (enExample) |
| DE (1) | DE2153902A1 (enExample) |
| ES (1) | ES407933A2 (enExample) |
| FR (1) | FR2158313B2 (enExample) |
| GB (1) | GB1348088A (enExample) |
| HU (1) | HU164715B (enExample) |
| IL (1) | IL40639A0 (enExample) |
| NL (1) | NL7214621A (enExample) |
| PL (1) | PL82632B1 (enExample) |
| SU (2) | SU509235A3 (enExample) |
| ZA (1) | ZA727504B (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2222834A1 (de) * | 1972-05-10 | 1973-11-29 | Boehringer Mannheim Gmbh | Nitrofuryl-amidin-derivate und verfahren zur herstellung derselben |
| ATE473980T1 (de) * | 2002-12-18 | 2010-07-15 | Vertex Pharma | Triazolopyridazine als proteinkinase-inhibitoren |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1527537A (fr) * | 1966-06-18 | 1968-05-31 | Boehringer & Soehne Gmbh | Procédé de préparation de nouveaux dérivés du 5-nitrofurane et du 5-nitrothiophène |
-
1971
- 1971-10-29 DE DE2153902A patent/DE2153902A1/de active Pending
-
1972
- 1972-10-22 IL IL40639A patent/IL40639A0/xx unknown
- 1972-10-23 ZA ZA727504A patent/ZA727504B/xx unknown
- 1972-10-23 DD DD166425A patent/DD102387A5/xx unknown
- 1972-10-24 ES ES407933A patent/ES407933A2/es not_active Expired
- 1972-10-24 GB GB4893772A patent/GB1348088A/en not_active Expired
- 1972-10-25 AR AR244808A patent/AR197008A1/es active
- 1972-10-27 NL NL7214621A patent/NL7214621A/xx unknown
- 1972-10-27 AT AT917072A patent/AT320628B/de not_active IP Right Cessation
- 1972-10-27 AU AU48277/72A patent/AU467712B2/en not_active Expired
- 1972-10-27 AT AT61774*A patent/ATA61774A/de not_active IP Right Cessation
- 1972-10-27 AT AT61874*7A patent/AT327883B/de not_active IP Right Cessation
- 1972-10-27 AT AT61774*7A patent/AT327882B/de not_active IP Right Cessation
- 1972-10-27 HU HUBO1401A patent/HU164715B/hu unknown
- 1972-10-27 AT AT61874*A patent/ATA61874A/de not_active IP Right Cessation
- 1972-10-27 FR FR7238198A patent/FR2158313B2/fr not_active Expired
- 1972-10-28 PL PL1972158524A patent/PL82632B1/pl unknown
- 1972-10-30 JP JP47108772A patent/JPS4852769A/ja active Pending
-
1973
- 1973-07-30 AR AR249346A patent/AR197055A1/es active
- 1973-07-30 AR AR249345A patent/AR197054A1/es active
-
1974
- 1974-04-19 SU SU2018983A patent/SU509235A3/ru active
- 1974-04-19 SU SU2018982A patent/SU511006A3/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| AR197055A1 (es) | 1974-03-08 |
| ATA61774A (de) | 1975-05-15 |
| HU164715B (enExample) | 1974-04-11 |
| IL40639A0 (en) | 1972-12-29 |
| ZA727504B (en) | 1973-08-29 |
| PL82632B1 (enExample) | 1975-10-31 |
| AT327882B (de) | 1976-02-25 |
| NL7214621A (enExample) | 1973-05-02 |
| ES407933A2 (es) | 1975-11-01 |
| ATA61874A (de) | 1975-05-15 |
| JPS4852769A (enExample) | 1973-07-24 |
| AU4827772A (en) | 1974-05-16 |
| DD102387A5 (enExample) | 1973-12-12 |
| DE2153902A1 (de) | 1973-05-03 |
| AR197054A1 (es) | 1974-03-08 |
| AU467712B2 (en) | 1975-12-11 |
| FR2158313B2 (enExample) | 1976-04-23 |
| SU511006A3 (ru) | 1976-04-15 |
| FR2158313A2 (enExample) | 1973-06-15 |
| AR197008A1 (es) | 1974-03-08 |
| AT320628B (de) | 1975-02-25 |
| GB1348088A (en) | 1974-03-13 |
| AT327883B (de) | 1976-02-25 |
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