DE1445438B2 - 3-amino-5-eckige klammer auf 5nitrofuryl-(2) eckige klammer zu-1,2,4triazole und deren salze mit nicht-toxischen saeuren sowie verfahren zur herstellung dieser verbindungen - Google Patents
3-amino-5-eckige klammer auf 5nitrofuryl-(2) eckige klammer zu-1,2,4triazole und deren salze mit nicht-toxischen saeuren sowie verfahren zur herstellung dieser verbindungenInfo
- Publication number
- DE1445438B2 DE1445438B2 DE19641445438 DE1445438A DE1445438B2 DE 1445438 B2 DE1445438 B2 DE 1445438B2 DE 19641445438 DE19641445438 DE 19641445438 DE 1445438 A DE1445438 A DE 1445438A DE 1445438 B2 DE1445438 B2 DE 1445438B2
- Authority
- DE
- Germany
- Prior art keywords
- triazole
- furyl
- compounds
- angle clamp
- amino
- 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.)
- Granted
Links
- 150000003839 salts Chemical class 0.000 title claims description 8
- 150000001875 compounds Chemical class 0.000 title description 23
- 238000000034 method Methods 0.000 title description 10
- 231100000252 nontoxic Toxicity 0.000 title description 6
- 230000003000 nontoxic effect Effects 0.000 title description 6
- 239000002253 acid Substances 0.000 title description 5
- 150000007513 acids Chemical class 0.000 title description 5
- 238000002360 preparation method Methods 0.000 title description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 10
- 238000010438 heat treatment Methods 0.000 claims description 4
- 150000007522 mineralic acids Chemical class 0.000 claims description 4
- 239000002585 base Substances 0.000 claims description 2
- 239000012458 free base Substances 0.000 claims description 2
- 239000000243 solution Substances 0.000 description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 17
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 15
- 239000000126 substance Substances 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 229910017604 nitric acid Inorganic materials 0.000 description 8
- -1 dichloroacetyl Chemical group 0.000 description 7
- 239000000155 melt Substances 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 238000006396 nitration reaction Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 150000003852 triazoles Chemical class 0.000 description 3
- 210000002700 urine Anatomy 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- 239000003929 acidic solution Substances 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 230000003472 neutralizing effect Effects 0.000 description 2
- ZODDGFAZWTZOSI-UHFFFAOYSA-N nitric acid;sulfuric acid Chemical compound O[N+]([O-])=O.OS(O)(=O)=O ZODDGFAZWTZOSI-UHFFFAOYSA-N 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 description 1
- HPBPNWPROCLLAA-UHFFFAOYSA-N 2-bromoethanone Chemical compound BrC[C]=O HPBPNWPROCLLAA-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical compound NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002170 ethers Chemical class 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
- 208000015181 infectious disease Diseases 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 244000000010 microbial pathogen Species 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 239000013558 reference substance Substances 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 210000001635 urinary tract Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom 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)
- Lighting Device Outwards From Vehicle And Optical Signal (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE219363 | 1963-02-28 | ||
| SE219363 | 1963-02-28 | ||
| SE1845/64A SE314381B (en, 2012) | 1964-02-15 | 1964-02-15 | |
| SE184564 | 1964-02-15 | ||
| DEA0045331 | 1964-02-26 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1445438A1 DE1445438A1 (de) | 1969-04-10 |
| DE1445438B2 true DE1445438B2 (de) | 1973-01-25 |
| DE1445438C DE1445438C (en, 2012) | 1973-08-30 |
Family
ID=26654296
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19641445438 Granted DE1445438B2 (de) | 1963-02-28 | 1964-02-26 | 3-amino-5-eckige klammer auf 5nitrofuryl-(2) eckige klammer zu-1,2,4triazole und deren salze mit nicht-toxischen saeuren sowie verfahren zur herstellung dieser verbindungen |
Country Status (6)
| Country | Link |
|---|---|
| CH (1) | CH424795A (en, 2012) |
| DE (1) | DE1445438B2 (en, 2012) |
| DK (1) | DK107619C (en, 2012) |
| GB (1) | GB1040551A (en, 2012) |
| NL (1) | NL6401901A (en, 2012) |
| NO (1) | NO115874B (en, 2012) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3522252A (en) * | 1968-04-03 | 1970-07-28 | R & L Molecular Research Ltd | Basic esters of 5-alkanoylamino-3-(5'-nitrofur - 2' - yl)isoxazole - 4 - carboxylic acid |
| US3522251A (en) * | 1968-04-03 | 1970-07-28 | R & L Molecular Research Ltd | Basic esters of 5-amino-3-(5'-nitrofur-2'-yl)isoxazole-4-carboxylic acid |
-
1964
- 1964-02-24 DK DK88164A patent/DK107619C/da active
- 1964-02-26 DE DE19641445438 patent/DE1445438B2/de active Granted
- 1964-02-27 NL NL6401901A patent/NL6401901A/xx unknown
- 1964-02-27 NO NO15220264A patent/NO115874B/no unknown
- 1964-02-27 GB GB810664A patent/GB1040551A/en not_active Expired
- 1964-02-28 CH CH249664A patent/CH424795A/fr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CH424795A (fr) | 1966-11-30 |
| DK107619C (da) | 1967-06-19 |
| NL6401901A (en, 2012) | 1964-08-31 |
| DE1445438A1 (de) | 1969-04-10 |
| GB1040551A (en) | 1966-09-01 |
| NO115874B (en, 2012) | 1968-12-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| SH | Request for examination between 03.10.1968 and 22.04.1971 | ||
| C3 | Grant after two publication steps (3rd publication) |