DE1093376B - Verfahren zur Herstellung von N-Dialkyl- und N-Diaralkylphosphorylhomocysteinthiolactonen - Google Patents
Verfahren zur Herstellung von N-Dialkyl- und N-DiaralkylphosphorylhomocysteinthiolactonenInfo
- Publication number
- DE1093376B DE1093376B DED31263A DED0031263A DE1093376B DE 1093376 B DE1093376 B DE 1093376B DE D31263 A DED31263 A DE D31263A DE D0031263 A DED0031263 A DE D0031263A DE 1093376 B DE1093376 B DE 1093376B
- Authority
- DE
- Germany
- Prior art keywords
- homocysteine
- reaction
- carried out
- added
- dialkyl
- 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 9
- FFFHZYDWPBMWHY-VKHMYHEASA-N L-homocysteine Chemical compound OC(=O)[C@@H](N)CCS FFFHZYDWPBMWHY-VKHMYHEASA-N 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 15
- -1 phosphoryl halide Chemical class 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- KIWQWJKWBHZMDT-UHFFFAOYSA-N homocysteine thiolactone Chemical compound NC1CCSC1=O KIWQWJKWBHZMDT-UHFFFAOYSA-N 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 4
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
- 239000000375 suspending agent Substances 0.000 claims description 3
- KGENPKAWPRUNIG-UHFFFAOYSA-N 1-[chloro(ethyl)phosphoryl]ethane Chemical compound CCP(Cl)(=O)CC KGENPKAWPRUNIG-UHFFFAOYSA-N 0.000 claims description 2
- ICKHJNMKQISCQZ-UHFFFAOYSA-N 2-[chloro(propan-2-yl)phosphoryl]propane Chemical compound CC(C)P(Cl)(=O)C(C)C ICKHJNMKQISCQZ-UHFFFAOYSA-N 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 2
- 150000003973 alkyl amines Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 238000003756 stirring Methods 0.000 claims description 2
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 claims description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 2
- 238000002844 melting Methods 0.000 claims 2
- 230000008018 melting Effects 0.000 claims 2
- 239000000706 filtrate Substances 0.000 claims 1
- 239000012299 nitrogen atmosphere Substances 0.000 claims 1
- 239000000725 suspension Substances 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000000370 acceptor Substances 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical class ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- OROGUZVNAFJPHA-UHFFFAOYSA-N 3-hydroxy-2,4-dimethyl-2H-thiophen-5-one Chemical group CC1SC(=O)C(C)=C1O OROGUZVNAFJPHA-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 1
- 206010067125 Liver injury Diseases 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- BEBCJVAWIBVWNZ-UHFFFAOYSA-N glycinamide Chemical compound NCC(N)=O BEBCJVAWIBVWNZ-UHFFFAOYSA-N 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 231100000234 hepatic damage Toxicity 0.000 description 1
- 208000006454 hepatitis Diseases 0.000 description 1
- 231100000283 hepatitis Toxicity 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000008818 liver damage Effects 0.000 description 1
- 230000007721 medicinal effect Effects 0.000 description 1
- 229930182817 methionine Natural products 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having sulfur atoms, with or without selenium or tellurium atoms, as the only ring hetero atoms
- C07F9/655345—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having sulfur atoms, with or without selenium or tellurium atoms, as the only ring hetero atoms the sulfur atom being part of a five-membered ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
- A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Organic Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Molecular Biology (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Biochemistry (AREA)
- Dermatology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL254206D NL254206A (en, 2012) | 1959-08-11 | ||
| NL105478D NL105478C (en, 2012) | 1959-08-11 | ||
| DED31263A DE1093376B (de) | 1959-08-11 | 1959-08-11 | Verfahren zur Herstellung von N-Dialkyl- und N-Diaralkylphosphorylhomocysteinthiolactonen |
| CH800860A CH389638A (de) | 1959-08-11 | 1960-07-13 | Verfahren zur Herstellung von N-Dialkyl- und N-Diaralkylphosphorylhomocysteinthiolacton |
| BE593539A BE593539A (fr) | 1959-08-11 | 1960-07-28 | Procédé pour la fabrication de N-Dialcoyl- et de N-Diaralcoylphosphorylhomocystérnothiolactones |
| US47596A US3068242A (en) | 1959-08-11 | 1960-08-05 | Production of n-dialkyl and n-diaralkyl phosphorylhomocysteine thiolactones |
| GB27863/60A GB903322A (en) | 1959-08-11 | 1960-08-11 | Process for the production of n-dialkyl and n-diaralkyl phosphoryl homocystein thiolactones |
| FR835607A FR1264942A (fr) | 1959-08-11 | 1960-08-11 | Procédé pour préparer les n-dialcoyl- et n-diaralcoyl-phosphoryl-homocystétinethiolactones |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DED31263A DE1093376B (de) | 1959-08-11 | 1959-08-11 | Verfahren zur Herstellung von N-Dialkyl- und N-Diaralkylphosphorylhomocysteinthiolactonen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1093376B true DE1093376B (de) | 1960-11-24 |
Family
ID=7040830
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DED31263A Pending DE1093376B (de) | 1959-08-11 | 1959-08-11 | Verfahren zur Herstellung von N-Dialkyl- und N-Diaralkylphosphorylhomocysteinthiolactonen |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3068242A (en, 2012) |
| BE (1) | BE593539A (en, 2012) |
| CH (1) | CH389638A (en, 2012) |
| DE (1) | DE1093376B (en, 2012) |
| GB (1) | GB903322A (en, 2012) |
| NL (2) | NL105478C (en, 2012) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4255443A (en) * | 1979-11-16 | 1981-03-10 | The United States Of America As Represented By The Department Of Health, Education And Welfare | Homocysteine thiolactone perchlorate as a tumor promotor |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2842527A (en) * | 1954-10-06 | 1958-07-08 | Rohm & Haas | Vinyl ether derivatives of amidophosphate and amidothiophosphate esters, their polymers and processes for preparing them |
| US2852550A (en) * | 1956-02-27 | 1958-09-16 | Monsanto Chemicals | Amidation of phosphorus halides with organic amines |
-
0
- NL NL254206D patent/NL254206A/xx unknown
- NL NL105478D patent/NL105478C/xx active
-
1959
- 1959-08-11 DE DED31263A patent/DE1093376B/de active Pending
-
1960
- 1960-07-13 CH CH800860A patent/CH389638A/de unknown
- 1960-07-28 BE BE593539A patent/BE593539A/fr unknown
- 1960-08-05 US US47596A patent/US3068242A/en not_active Expired - Lifetime
- 1960-08-11 GB GB27863/60A patent/GB903322A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL254206A (en, 2012) | |
| US3068242A (en) | 1962-12-11 |
| NL105478C (en, 2012) | |
| GB903322A (en) | 1962-08-15 |
| BE593539A (fr) | 1960-11-14 |
| CH389638A (de) | 1965-03-31 |
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