DE1134996B - Verfahren zur Herstellung neuer, bakteriostatisch wirksamer Nitrofurylthiadiazole - Google Patents
Verfahren zur Herstellung neuer, bakteriostatisch wirksamer NitrofurylthiadiazoleInfo
- Publication number
- DE1134996B DE1134996B DEA35104A DEA0035104A DE1134996B DE 1134996 B DE1134996 B DE 1134996B DE A35104 A DEA35104 A DE A35104A DE A0035104 A DEA0035104 A DE A0035104A DE 1134996 B DE1134996 B DE 1134996B
- Authority
- DE
- Germany
- Prior art keywords
- new
- nitrofurylthiadiazoles
- thiadiazole
- production
- nitrofuryl
- 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 6
- OEBUQQJTQXRLSZ-UHFFFAOYSA-N 4-(furan-2-yl)-5-nitrothiadiazole Chemical class [N+](=O)([O-])C1=C(N=NS1)C=1OC=CC=1 OEBUQQJTQXRLSZ-UHFFFAOYSA-N 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 229910052717 sulfur Chemical group 0.000 claims description 3
- 239000011593 sulfur Chemical group 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 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
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 150000002391 heterocyclic compounds Chemical class 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 238000000354 decomposition reaction Methods 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 230000000844 anti-bacterial effect Effects 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 125000003277 amino group Chemical group 0.000 description 4
- 244000005700 microbiome Species 0.000 description 4
- -1 nitrofuryl group Chemical group 0.000 description 4
- SXZZHGJWUBJKHH-UHFFFAOYSA-N 2-Amino-5-(5-nitro-2-furyl)-1,3,4-thiadiazole Chemical compound S1C(N)=NN=C1C1=CC=C([N+]([O-])=O)O1 SXZZHGJWUBJKHH-UHFFFAOYSA-N 0.000 description 3
- 230000003385 bacteriostatic effect Effects 0.000 description 3
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 3
- 210000002966 serum Anatomy 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 206010008631 Cholera Diseases 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 241000293869 Salmonella enterica subsp. enterica serovar Typhimurium Species 0.000 description 2
- IAIWVQXQOWNYOU-FPYGCLRLSA-N nitrofural Chemical class NC(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 IAIWVQXQOWNYOU-FPYGCLRLSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- FWSYYTQNROEZQP-UHFFFAOYSA-N 5-(5-nitrofuran-2-yl)-n-phenyl-1,3,4-thiadiazol-2-amine Chemical compound O1C([N+](=O)[O-])=CC=C1C(S1)=NN=C1NC1=CC=CC=C1 FWSYYTQNROEZQP-UHFFFAOYSA-N 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- ISTLEQBEBWKYAM-UHFFFAOYSA-N N-benzyl-5-(5-nitrofuran-2-yl)-1,3,4-thiadiazol-2-amine Chemical compound O1C([N+](=O)[O-])=CC=C1C(S1)=NN=C1NCC1=CC=CC=C1 ISTLEQBEBWKYAM-UHFFFAOYSA-N 0.000 description 1
- 241000531795 Salmonella enterica subsp. enterica serovar Paratyphi A Species 0.000 description 1
- 241000293871 Salmonella enterica subsp. enterica serovar Typhi Species 0.000 description 1
- 208000037386 Typhoid Diseases 0.000 description 1
- XWUHTDIIQSYUDH-UHFFFAOYSA-N [(5-nitrofuran-2-yl)methylideneamino]thiourea Chemical compound NC(=S)NN=CC1=CC=C([N+]([O-])=O)O1 XWUHTDIIQSYUDH-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 229940124350 antibacterial drug Drugs 0.000 description 1
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000012888 bovine serum Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 230000009036 growth inhibition Effects 0.000 description 1
- BRWIZMBXBAOCCF-UHFFFAOYSA-N hydrazinecarbothioamide Chemical compound NNC(N)=S BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 description 1
- 125000006316 iso-butyl amino group Chemical group [H]N(*)C([H])([H])C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000002004 n-butylamino group Chemical group [H]N(*)C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- RAUJDUMBXIFDMJ-UHFFFAOYSA-N n-methyl-5-(5-nitrofuran-2-yl)-1,3,4-thiadiazol-2-amine Chemical compound S1C(NC)=NN=C1C1=CC=C([N+]([O-])=O)O1 RAUJDUMBXIFDMJ-UHFFFAOYSA-N 0.000 description 1
- 125000004888 n-propyl amino group Chemical group [H]N(*)C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000017066 negative regulation of growth Effects 0.000 description 1
- 150000003015 phosphoric acid halides Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 150000004867 thiadiazoles Chemical group 0.000 description 1
- 201000008827 tuberculosis Diseases 0.000 description 1
- 201000008297 typhoid fever Diseases 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE659459 | 1959-07-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1134996B true DE1134996B (de) | 1962-08-23 |
Family
ID=88292812
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEA35104A Pending DE1134996B (de) | 1959-07-13 | 1960-07-12 | Verfahren zur Herstellung neuer, bakteriostatisch wirksamer Nitrofurylthiadiazole |
Country Status (3)
| Country | Link |
|---|---|
| DE (1) | DE1134996B (en, 2012) |
| FR (1) | FR702M (en, 2012) |
| NL (1) | NL253749A (en, 2012) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1171927B (de) * | 1962-10-01 | 1964-06-11 | Haruo Saikachi | Verfahren zur Herstellung von 5-(5-Nitro-2-furyl-vinylen)-1, 3, 4-oxadiazolinonen-(2) |
| DE1213850B (de) * | 1962-12-19 | 1966-04-07 | Boehringer & Soehne Gmbh | Verfahren zur Herstellung von 5-Nitrofuran-Derivaten |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1077220B (de) * | 1957-09-30 | 1960-03-10 | Pharmacia Ab | Verfahren zur Herstellung von bakteriostatisch wirkenden 5-Amino-2-(5-nitrofuryl)-1,3, 4-thiadiazolen |
-
1960
- 1960-07-12 DE DEA35104A patent/DE1134996B/de active Pending
- 1960-07-13 NL NL253749D patent/NL253749A/nl unknown
- 1960-10-10 FR FR840743A patent/FR702M/fr active Active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1077220B (de) * | 1957-09-30 | 1960-03-10 | Pharmacia Ab | Verfahren zur Herstellung von bakteriostatisch wirkenden 5-Amino-2-(5-nitrofuryl)-1,3, 4-thiadiazolen |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1171927B (de) * | 1962-10-01 | 1964-06-11 | Haruo Saikachi | Verfahren zur Herstellung von 5-(5-Nitro-2-furyl-vinylen)-1, 3, 4-oxadiazolinonen-(2) |
| DE1213850B (de) * | 1962-12-19 | 1966-04-07 | Boehringer & Soehne Gmbh | Verfahren zur Herstellung von 5-Nitrofuran-Derivaten |
Also Published As
| Publication number | Publication date |
|---|---|
| NL253749A (en, 2012) | 1964-03-25 |
| FR702M (en, 2012) | 1961-07-31 |
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