DE2045818A1 - Aeruginoinsäure und Verfahren zu ihrer Herstellung - Google Patents
Aeruginoinsäure und Verfahren zu ihrer HerstellungInfo
- Publication number
- DE2045818A1 DE2045818A1 DE19702045818 DE2045818A DE2045818A1 DE 2045818 A1 DE2045818 A1 DE 2045818A1 DE 19702045818 DE19702045818 DE 19702045818 DE 2045818 A DE2045818 A DE 2045818A DE 2045818 A1 DE2045818 A1 DE 2045818A1
- Authority
- DE
- Germany
- Prior art keywords
- acid
- aeruginoic
- ester
- preparation
- converted
- 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
- UCVBEULMPJTLLH-UHFFFAOYSA-N 2-(2-hydroxyphenyl)-1,3-thiazole-4-carboxylic acid Chemical compound OC(=O)C1=CSC(C=2C(=CC=CC=2)O)=N1 UCVBEULMPJTLLH-UHFFFAOYSA-N 0.000 title claims description 48
- 238000000034 method Methods 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 150000002148 esters Chemical class 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 229940107700 pyruvic acid Drugs 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 1
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000013078 crystal Substances 0.000 description 4
- 125000004494 ethyl ester group Chemical group 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- -1 o-hydroxy-phenyl Chemical group 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 241000123650 Botrytis cinerea Species 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- 241000589516 Pseudomonas Species 0.000 description 1
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7325169 | 1969-09-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2045818A1 true DE2045818A1 (de) | 1971-04-08 |
Family
ID=13512759
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702045818 Pending DE2045818A1 (de) | 1969-09-17 | 1970-09-16 | Aeruginoinsäure und Verfahren zu ihrer Herstellung |
Country Status (5)
| Country | Link |
|---|---|
| DE (1) | DE2045818A1 (https=) |
| FR (1) | FR2062210A5 (https=) |
| GB (1) | GB1292170A (https=) |
| IT (1) | IT1050117B (https=) |
| NL (1) | NL7013787A (https=) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3002989A1 (de) * | 1980-01-29 | 1981-07-30 | Hoechst Ag, 6000 Frankfurt | Hydroxyphenyl-thiazol, -thiazolin und -thiazolidin-carbonsaeuren, verfahren zu ihrer herstellung und ihre verwendung zur beeinflussung des kollagenstoffwechsels |
| US6083966A (en) | 1998-08-31 | 2000-07-04 | University Of Florida | Thiazoline acid derivatives |
| WO2000016763A2 (en) | 1998-09-21 | 2000-03-30 | University Of Florida Research Foundation, Inc. | Antimalarial agents |
| US7002036B2 (en) | 2002-05-15 | 2006-02-21 | Genzyme Corporation | Synthesis of 2-alkyl amino acids |
| WO2005034949A1 (en) | 2003-09-09 | 2005-04-21 | University Of Florida | Desferrithiocin derivatives and their use as iron chelators |
| BRPI0610644B8 (pt) | 2005-04-04 | 2021-05-25 | Univ Florida | composto e composição farmacêutica que compreende tal composto e um veículo ou diluente farmaceuticamente aceitável. |
| JP5439193B2 (ja) | 2007-03-15 | 2014-03-12 | ユニバーシティー オブ フロリダ リサーチ ファンデーション， インク． | デスフェリチオシンポリエーテル類似体 |
| JP6539046B2 (ja) | 2011-12-16 | 2019-07-03 | ユニバーシティー オブ フロリダ リサーチ ファンデーション， インク． | ４’−デスフェリチオシン類似体の使用 |
| CA2930966A1 (en) | 2013-11-22 | 2015-05-28 | University Of Florida Research Foundation, Inc. | Desferrithiocin analogs and uses thereof |
| EP3288557A4 (en) | 2015-04-27 | 2018-11-07 | University of Florida Research Foundation, Inc. | Metabolically programmed metal chelators and uses thereof |
-
1970
- 1970-09-16 FR FR7033604A patent/FR2062210A5/fr not_active Expired
- 1970-09-16 DE DE19702045818 patent/DE2045818A1/de active Pending
- 1970-09-16 IT IT2977970A patent/IT1050117B/it active
- 1970-09-17 NL NL7013787A patent/NL7013787A/xx unknown
- 1970-09-17 GB GB4454370A patent/GB1292170A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| IT1050117B (it) | 1981-03-10 |
| NL7013787A (https=) | 1971-03-19 |
| GB1292170A (en) | 1972-10-11 |
| FR2062210A5 (https=) | 1971-06-25 |
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