GB937931A - Dibenzyloxyphosphoryl creatinine and a process for the preparation of phosphocreatine and/or phosphocreatinine therefrom - Google Patents
Dibenzyloxyphosphoryl creatinine and a process for the preparation of phosphocreatine and/or phosphocreatinine therefromInfo
- Publication number
- GB937931A GB937931A GB32822/59A GB3282259A GB937931A GB 937931 A GB937931 A GB 937931A GB 32822/59 A GB32822/59 A GB 32822/59A GB 3282259 A GB3282259 A GB 3282259A GB 937931 A GB937931 A GB 937931A
- Authority
- GB
- United Kingdom
- Prior art keywords
- dibenzyloxyphosphoryl
- caustic soda
- phosphocreatine
- creatinine
- reacting
- 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
- -1 Dibenzyloxyphosphoryl creatinine Chemical compound 0.000 title abstract 8
- DRBBFCLWYRJSJZ-UHFFFAOYSA-N N-phosphocreatine Chemical compound OC(=O)CN(C)C(=N)NP(O)(O)=O DRBBFCLWYRJSJZ-UHFFFAOYSA-N 0.000 title abstract 8
- 229950007002 phosphocreatine Drugs 0.000 title abstract 5
- 229940109239 creatinine Drugs 0.000 title abstract 4
- DDRJAANPRJIHGJ-UHFFFAOYSA-N creatinine Natural products CN1CC(=O)NC1=N DDRJAANPRJIHGJ-UHFFFAOYSA-N 0.000 title abstract 4
- HIPLEPXPNLWKCQ-UHFFFAOYSA-N fosfocreatinine Chemical compound CN1CC(=O)N=C1NP(O)(O)=O HIPLEPXPNLWKCQ-UHFFFAOYSA-N 0.000 title abstract 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 15
- 235000011121 sodium hydroxide Nutrition 0.000 abstract 5
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 abstract 4
- 230000001476 alcoholic effect Effects 0.000 abstract 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 abstract 2
- 239000003054 catalyst Substances 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 238000005984 hydrogenation reaction Methods 0.000 abstract 2
- 159000000000 sodium salts Chemical class 0.000 abstract 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 abstract 2
- BZZXQZOBAUXLHZ-UHFFFAOYSA-N (c-methylsulfanylcarbonimidoyl)azanium;sulfate Chemical compound CSC(N)=N.CSC(N)=N.OS(O)(=O)=O BZZXQZOBAUXLHZ-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- CVSVTCORWBXHQV-UHFFFAOYSA-N anhydrous creatine Natural products NC(=[NH2+])N(C)CC([O-])=O CVSVTCORWBXHQV-UHFFFAOYSA-N 0.000 abstract 1
- 229960003624 creatine Drugs 0.000 abstract 1
- 239000006046 creatine Substances 0.000 abstract 1
- BTKSUULMJNNXHG-UHFFFAOYSA-N ethyl 2-(methylamino)acetate Chemical compound CCOC(=O)CNC BTKSUULMJNNXHG-UHFFFAOYSA-N 0.000 abstract 1
- 238000007327 hydrogenolysis reaction Methods 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- UKWHYYKOEPRTIC-UHFFFAOYSA-N mercury(ii) oxide Chemical compound [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 abstract 1
- SDDKIZNHOCEXTF-UHFFFAOYSA-N methyl carbamimidothioate Chemical class CSC(N)=N SDDKIZNHOCEXTF-UHFFFAOYSA-N 0.000 abstract 1
- RQKYHDHLEMEVDR-UHFFFAOYSA-N oxo-bis(phenylmethoxy)phosphanium Chemical compound C=1C=CC=CC=1CO[P+](=O)OCC1=CC=CC=C1 RQKYHDHLEMEVDR-UHFFFAOYSA-N 0.000 abstract 1
- 150000003385 sodium Chemical class 0.000 abstract 1
- 229910000029 sodium carbonate Inorganic materials 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
- C07F9/22—Amides of acids of phosphorus
- C07F9/24—Esteramides
- C07F9/2454—Esteramides the amide moiety containing a substituent or a structure which is considered as characteristic
- C07F9/2458—Esteramides the amide moiety containing a substituent or a structure which is considered as characteristic of aliphatic amines
-
- 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
- C07F9/22—Amides of acids of phosphorus
- C07F9/222—Amides of phosphoric acids
-
- 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
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6503—Five-membered rings
- C07F9/6506—Five-membered rings having the nitrogen atoms in positions 1 and 3
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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention comprises dibenzyl-oxyphosphoryl creatinine having the formula:- <FORM:0937931/IV(a)/1> It may be obtained by first preparing the N-dibenzyl-oxy-phosphorylated derivative of S-methyl isothiourea of the formula:- <FORM:0937931/IV(a)/2> by the action of dibenzyl phosphite in solution in carbon tetrachloride on S-methylisothiouronium sulphate in the presence of caustic soda, reacting the isothiourea compound in ethanol with red oxide of mercury in the presence of sodium carbonate to form the sodium derivative of dibenzyloxyphosphoryl cyanamide of the formula:- <FORM:0937931/IV(a)/3> reacting the latter in alcoholic medium with the hydrochloride of ethyl sarcosinate to form dibenzyloxy-phosphoryl ethyl creatinate, hydrolysing the latter in aqueous alcoholic medium, to form the sodium salt of dibenzyloxy phosphoryl creatine and finally acidifying the latter with a weak acid, e.g. acetic acid. The dibenzyloxyphosphoryl creatinine may be converted to the disodium salt of phosphocreatinine by reacting it with hydrogen in aqueous alcoholic medium in the presence of a hydrogenation catalyst, e.g. palladium black, and caustic soda at a temperature below 30 DEG C. and the product on further treatment with caustic soda at above 30 DEG C. is converted to the disodium salt of phosphocreatine of the formula:- <FORM:0937931/IV(a)/4> The phosphocreatine may also be obtained as its disodium salt by reacting dibenzyloxyphosphoryl creatinine in aqueous alcoholic medium with hydrogen in the presence of a hydrogenation catalyst and caustic soda at a temperature above 30 DEG C. The sodium salt of dibenzyloxyphosphoryl creatine referred to above can also be subjected to hydrogenolysis in the presence of palladium black and caustic soda to form the disodium salt of phosphocreatine.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR775394 | 1958-09-26 | ||
| FR775839 | 1958-10-03 | ||
| FR789130A FR75327E (en) | 1959-03-12 | 1959-03-12 | Process for the synthesis of phosphocreatinine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB937931A true GB937931A (en) | 1963-09-25 |
Family
ID=27245193
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB32822/59A Expired GB937931A (en) | 1958-09-26 | 1959-09-28 | Dibenzyloxyphosphoryl creatinine and a process for the preparation of phosphocreatine and/or phosphocreatinine therefrom |
Country Status (3)
| Country | Link |
|---|---|
| CH (2) | CH401989A (en) |
| DE (1) | DE1793730C3 (en) |
| GB (1) | GB937931A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0754679A1 (en) * | 1995-07-18 | 1997-01-22 | SKW Trostberg Aktiengesellschaft | Process for the preparation of creatin or creatine-monohydrate |
| WO2009033130A1 (en) * | 2007-09-07 | 2009-03-12 | Gencia Corporation | Mitochondrial compositions and uses thereof |
| CN102153587A (en) * | 2011-03-07 | 2011-08-17 | 南京亚东启天药业有限公司 | Method for synthesizing dibenzyloxy-phosphoryl creatinine |
| CN102558227A (en) * | 2011-12-29 | 2012-07-11 | 中山百灵生物技术有限公司 | Novel method for preparing high-purity creatine phosphate sodium |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1173206B (en) * | 1984-02-02 | 1987-06-18 | Italiana Sint Spa | PROCEDURE FOR THE PREPARATION OF N- (DIBENZYLSYPHOSPHORYL) CYANAMIDE, COMPOUND SO OBTAINED, PROCESSES THAT USE THIS COMPOUND AS INTERMEDIATE SYNTHESIS OF PHOSPHAGEN SUBSTANCES AND SUBSTANCES IN SUCH A WAY PRODUCED |
-
1959
- 1959-09-15 CH CH752565A patent/CH401989A/en unknown
- 1959-09-15 CH CH7825059A patent/CH395110A/en unknown
- 1959-09-24 DE DE1793730A patent/DE1793730C3/en not_active Expired
- 1959-09-28 GB GB32822/59A patent/GB937931A/en not_active Expired
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0754679A1 (en) * | 1995-07-18 | 1997-01-22 | SKW Trostberg Aktiengesellschaft | Process for the preparation of creatin or creatine-monohydrate |
| US5719319A (en) * | 1995-07-18 | 1998-02-17 | Skw Trostberg Aktiengesellschaft | Process for the preparation of a creatine or creatine monohydrate |
| WO2009033130A1 (en) * | 2007-09-07 | 2009-03-12 | Gencia Corporation | Mitochondrial compositions and uses thereof |
| CN102153587A (en) * | 2011-03-07 | 2011-08-17 | 南京亚东启天药业有限公司 | Method for synthesizing dibenzyloxy-phosphoryl creatinine |
| CN102153587B (en) * | 2011-03-07 | 2013-01-23 | 南京亚东启天药业有限公司 | Method for synthesizing dibenzyloxy-phosphoryl creatinine |
| CN102558227A (en) * | 2011-12-29 | 2012-07-11 | 中山百灵生物技术有限公司 | Novel method for preparing high-purity creatine phosphate sodium |
| CN102558227B (en) * | 2011-12-29 | 2015-01-28 | 中山百灵生物技术有限公司 | Novel method for preparing high-purity creatine phosphate sodium |
Also Published As
| Publication number | Publication date |
|---|---|
| CH401989A (en) | 1965-11-15 |
| DE1793730A1 (en) | 1973-02-08 |
| DE1518793A1 (en) | 1969-02-20 |
| DE1793730B2 (en) | 1973-07-05 |
| CH395110A (en) | 1965-07-15 |
| DE1793730C3 (en) | 1974-02-07 |
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