GB766536A - Improvements in or relating to the manufacture of pentetheine-4-phosphate - Google Patents
Improvements in or relating to the manufacture of pentetheine-4-phosphateInfo
- Publication number
- GB766536A GB766536A GB77953A GB77953A GB766536A GB 766536 A GB766536 A GB 766536A GB 77953 A GB77953 A GB 77953A GB 77953 A GB77953 A GB 77953A GB 766536 A GB766536 A GB 766536A
- Authority
- GB
- United Kingdom
- Prior art keywords
- aralkyl
- protected
- pantetheine
- phosphate
- hydrogenolysis
- 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 4
- 239000010452 phosphate Substances 0.000 title abstract 4
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- GHOKWGTUZJEAQD-ZETCQYMHSA-N (D)-(+)-Pantothenic acid Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-ZETCQYMHSA-N 0.000 abstract 6
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 abstract 6
- GHOKWGTUZJEAQD-UHFFFAOYSA-N Chick antidermatitis factor Natural products OCC(C)(C)C(O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-UHFFFAOYSA-N 0.000 abstract 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 4
- 235000019161 pantothenic acid Nutrition 0.000 abstract 4
- 239000011713 pantothenic acid Substances 0.000 abstract 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 3
- 150000008064 anhydrides Chemical class 0.000 abstract 3
- 238000007327 hydrogenolysis reaction Methods 0.000 abstract 3
- 229940055726 pantothenic acid Drugs 0.000 abstract 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- 159000000009 barium salts Chemical class 0.000 abstract 2
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 abstract 2
- 229910003002 lithium salt Inorganic materials 0.000 abstract 2
- 159000000002 lithium salts Chemical class 0.000 abstract 2
- 229960003151 mercaptamine Drugs 0.000 abstract 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 2
- 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 2
- PNCWHIAZZSDHPU-UHFFFAOYSA-N 2-benzylsulfanylethanamine Chemical compound NCCSCC1=CC=CC=C1 PNCWHIAZZSDHPU-UHFFFAOYSA-N 0.000 abstract 1
- 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
- ZNXZGRMVNNHPCA-UHFFFAOYSA-N Pantetheine Natural products OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS ZNXZGRMVNNHPCA-UHFFFAOYSA-N 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
- 239000002253 acid Substances 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 150000001727 carbonic acid monoesters Chemical class 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- UFULAYFCSOUIOV-UHFFFAOYSA-N cysteamine Chemical compound NCCS UFULAYFCSOUIOV-UHFFFAOYSA-N 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 abstract 1
- 150000007530 organic bases Chemical group 0.000 abstract 1
- ZNXZGRMVNNHPCA-VIFPVBQESA-N pantetheine Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCC(=O)NCCS ZNXZGRMVNNHPCA-VIFPVBQESA-N 0.000 abstract 1
- 229940115458 pantolactone Drugs 0.000 abstract 1
- 230000026731 phosphorylation Effects 0.000 abstract 1
- 238000006366 phosphorylation reaction Methods 0.000 abstract 1
- 230000001376 precipitating effect Effects 0.000 abstract 1
- 229910052709 silver Inorganic materials 0.000 abstract 1
- 239000004332 silver Substances 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 125000005270 trialkylamine group Chemical group 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises 021 : S-aralkyl-protected pantetheines and comprises also a method of making 02 : S-aralkyl protected pantetheines in which an S-aralkyl-protected 2-mercaptoethylamine is condensed with a mixed anhydride of an O2-aralkyl protected pantothenic acid and a carbonic acid mono ester. Preferably the mixed anhydride is a compound of the formula R.CO.O.CO.OR1 where R is an 021-aralkyl protected pantothenic acid residue of the formula HO.CH2.C.(CH3)2.CH(OR2).CO. NH.CH2CH2, wherein R2 is an aralkyl group and R1 is an alkyl group of up to five carbon atoms. Suitably a mixed anhydride, obtained by condensation of an 021-aralkyl-protected pantothenic acid with a halogenoformic ester such as ethyl chloroformate in the presence of a strong tertiary base such as a trialkylamine or N - methyl - morpholine at - 10 DEG C. to 0 DEG C., is condensed with an S-aralkyl-2-mercaptoethylamine at - 20 DEG C. to + 20 DEG C. The resulting 021 : S-aralkyl-protected pantetheine may be converted into pantetheine-41-phosphate by treating it under anhydrous conditions in the presence of a tertiary organic base with a diaralkyl halogenophosphonate followed by hydrogenolysis to remove the aralkyl groups. Suitably the phosphorylation is effected by treatment with a dibenzyl-halogenophosphonate at - 40 DEG C. to 0 DEG C. in the presence of a pyridine base and hydrogenolysis is effected by treatment with an alkali-metal in liquid ammonia. The pantetheine-41-phosphate is purified by forming the lithium salt, precipitating the silver salt therefrom and converting the silver salt into the barium salt. In an example 021-benzylpantothenic acid is treated with ethyl chloroformate in dimethylformamide in the presence of N-methyl-morpholine, the product is reacted with S-benzyl-2-mercapto ethylamine to give 021 : S-dibenzyl-pantetheine which is phosphorylated by dibenzyl chlorophosphonate in the presence of pyridine followed by hydrogenolysis by sodium in liquid ammonia to give pantetheine-41-phosphate which is separated as the lithium salt and purified via the silver and barium salts. Starting material. 021 - Benzyl - panthothenic acid is made by treating 02-benzyl-pantolactone with b -alanine in the presence of dimethylamine. Specifications 702,750 and 716,337 are referred to.
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE525587D BE525587A (en) | 1953-01-09 | ||
| GB77953A GB766536A (en) | 1953-01-09 | 1953-01-09 | Improvements in or relating to the manufacture of pentetheine-4-phosphate |
| FR1096257D FR1096257A (en) | 1953-01-09 | 1954-01-05 | Process for preparing pantethein 4'-phosphate |
| DEN8289A DE1001996B (en) | 1953-01-09 | 1954-01-09 | Process for the preparation of pantethein-4'-phosphate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB77953A GB766536A (en) | 1953-01-09 | 1953-01-09 | Improvements in or relating to the manufacture of pentetheine-4-phosphate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB766536A true GB766536A (en) | 1957-01-23 |
Family
ID=9710367
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB77953A Expired GB766536A (en) | 1953-01-09 | 1953-01-09 | Improvements in or relating to the manufacture of pentetheine-4-phosphate |
Country Status (4)
| Country | Link |
|---|---|
| BE (1) | BE525587A (en) |
| DE (1) | DE1001996B (en) |
| FR (1) | FR1096257A (en) |
| GB (1) | GB766536A (en) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE884796C (en) * | 1951-04-03 | 1953-07-30 | Boehringer Sohn Ingelheim | Process for the preparation of N- [ª ‡ ', ª ‰' - Dioxy-ª ‰ ', ª ‰ -dimethyl-butyryl] -ª ‰ -alanine-ª ‰ "- mercapto-ethylamide |
-
0
- BE BE525587D patent/BE525587A/xx unknown
-
1953
- 1953-01-09 GB GB77953A patent/GB766536A/en not_active Expired
-
1954
- 1954-01-05 FR FR1096257D patent/FR1096257A/en not_active Expired
- 1954-01-09 DE DEN8289A patent/DE1001996B/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| FR1096257A (en) | 1955-06-17 |
| DE1001996B (en) | 1957-02-07 |
| BE525587A (en) |
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