GB749512A - Improvements in or relating to the manufacture of pantetheine-4-phosphate and pantethine-4-phosphate - Google Patents
Improvements in or relating to the manufacture of pantetheine-4-phosphate and pantethine-4-phosphateInfo
- Publication number
- GB749512A GB749512A GB78153A GB78153A GB749512A GB 749512 A GB749512 A GB 749512A GB 78153 A GB78153 A GB 78153A GB 78153 A GB78153 A GB 78153A GB 749512 A GB749512 A GB 749512A
- Authority
- GB
- United Kingdom
- Prior art keywords
- pantetheine
- pantethine
- phosphate
- treated
- oxygen
- 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.)
- Expired
Links
- 229910019142 PO4 Inorganic materials 0.000 title abstract 7
- 239000010452 phosphate Substances 0.000 title abstract 7
- 238000004519 manufacturing process Methods 0.000 title 1
- JJLJMEJHUUYSSY-UHFFFAOYSA-L Copper hydroxide Chemical compound [OH-].[OH-].[Cu+2] JJLJMEJHUUYSSY-UHFFFAOYSA-L 0.000 abstract 4
- ZNXZGRMVNNHPCA-UHFFFAOYSA-N Pantetheine Natural products OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS ZNXZGRMVNNHPCA-UHFFFAOYSA-N 0.000 abstract 4
- DJWYOLJPSHDSAL-UHFFFAOYSA-N Pantethine Natural products OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSSCCNC(=O)CCNC(=O)C(O)C(C)(C)CO DJWYOLJPSHDSAL-UHFFFAOYSA-N 0.000 abstract 4
- 159000000009 barium salts Chemical class 0.000 abstract 4
- ZNXZGRMVNNHPCA-VIFPVBQESA-N pantetheine Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCC(=O)NCCS ZNXZGRMVNNHPCA-VIFPVBQESA-N 0.000 abstract 4
- DJWYOLJPSHDSAL-ROUUACIJSA-N pantethine Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCC(=O)NCCSSCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)CO DJWYOLJPSHDSAL-ROUUACIJSA-N 0.000 abstract 4
- 229960000903 pantethine Drugs 0.000 abstract 4
- 235000008975 pantethine Nutrition 0.000 abstract 4
- 239000011581 pantethine Substances 0.000 abstract 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 3
- 229910052760 oxygen Inorganic materials 0.000 abstract 3
- 239000001301 oxygen Substances 0.000 abstract 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- 239000003153 chemical reaction reagent Substances 0.000 abstract 2
- 230000000694 effects Effects 0.000 abstract 2
- 238000007327 hydrogenolysis reaction Methods 0.000 abstract 2
- 238000001556 precipitation Methods 0.000 abstract 2
- 150000003222 pyridines Chemical class 0.000 abstract 2
- 239000007858 starting material Substances 0.000 abstract 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 1
- YADJFRGSGWGMNH-UHFFFAOYSA-N [chloro(phenylmethoxy)phosphoryl]oxymethylbenzene Chemical compound C=1C=CC=CC=1COP(=O)(Cl)OCC1=CC=CC=C1 YADJFRGSGWGMNH-UHFFFAOYSA-N 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 125000005263 alkylenediamine group Chemical group 0.000 abstract 1
- 239000002585 base Substances 0.000 abstract 1
- 239000003638 chemical reducing agent Substances 0.000 abstract 1
- 150000007530 organic bases Chemical group 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 238000001226 reprecipitation Methods 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/091—Esters of phosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Catalysts (AREA)
Abstract
A product containing pantethine-41-phosphate and/or pantetheine-41-phosphate is made by treating pantethine with a diaralkyl halogenophosphonate under anhydrous conditions in the presence of a tertiary organic base such as a member of the pyridine series, preferably at -40 DEG C. to 0 DEG C., and treating the pantethine-41-diaralkyl phosphate formed, with a hydrogenolysis reagent such as an alkali metal in liquid ammonia followed by treatment with a reducing agent if required, to effect at least partial disulphide-to-thiol reduction. Suitably the hydrogenolysis reagent is used to effect both dearalkylation and also the disulphide-to-thiol reduction. The product may be purified by successive barium salt precipitation, silver salt precipitation and finally repricipitation as the barium salt. The pantethine used as a starting material may be obtained by oxidizing pantetheine, preferably by passing oxygen through a solution of pantetheine in a basic solvent which may for example consist at least in part of a tertiary base of the pyridine series or an alkylene diamine such as ethylene diamine which has cupric hydroxide associated with it. Preferably the starting materials and products are in the D(+) form. In examples (1) oxygen is passed into a solution of pantetheine in pyridine, the product is treated with dibenzylchlorophosphonate followed by reduction with sodium in liquid ammonia and the resulting pantethine - 41 - phosphate and pantetheine-41-phosphate are separated as barium salts and are purified by successive reprecipitation as the silver salts and barium salts; (2) pantetheine is treated with oxygen in ethylene diamine containing cupric hydroxide and the resulting pantethine is treated as in (1).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB78153A GB749512A (en) | 1953-01-09 | 1953-01-09 | Improvements in or relating to the manufacture of pantetheine-4-phosphate and pantethine-4-phosphate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB78153A GB749512A (en) | 1953-01-09 | 1953-01-09 | Improvements in or relating to the manufacture of pantetheine-4-phosphate and pantethine-4-phosphate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB749512A true GB749512A (en) | 1956-05-30 |
Family
ID=9710394
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB78153A Expired GB749512A (en) | 1953-01-09 | 1953-01-09 | Improvements in or relating to the manufacture of pantetheine-4-phosphate and pantethine-4-phosphate |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB749512A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011030727A1 (en) | 2009-09-11 | 2011-03-17 | 第一ファインケミカル株式会社 | External preparation containing pantethine phosphate ester |
-
1953
- 1953-01-09 GB GB78153A patent/GB749512A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011030727A1 (en) | 2009-09-11 | 2011-03-17 | 第一ファインケミカル株式会社 | External preparation containing pantethine phosphate ester |
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