US2653897A - Alkali metal salts of adenylic acid - Google Patents
Alkali metal salts of adenylic acid Download PDFInfo
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- US2653897A US2653897A US98406A US9840649A US2653897A US 2653897 A US2653897 A US 2653897A US 98406 A US98406 A US 98406A US 9840649 A US9840649 A US 9840649A US 2653897 A US2653897 A US 2653897A
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- acid
- adenylic acid
- solution
- alkali metal
- metal salts
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- UDMBCSSLTHHNCD-KQYNXXCUSA-N adenosine 5'-monophosphate Chemical class C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O UDMBCSSLTHHNCD-KQYNXXCUSA-N 0.000 title claims description 37
- UDMBCSSLTHHNCD-UHFFFAOYSA-N Coenzym Q(11) Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(O)=O)C(O)C1O UDMBCSSLTHHNCD-UHFFFAOYSA-N 0.000 title claims description 26
- 229950006790 adenosine phosphate Drugs 0.000 title claims description 26
- 229910052783 alkali metal Inorganic materials 0.000 title description 13
- -1 Alkali metal salts Chemical class 0.000 title description 12
- 239000007864 aqueous solution Substances 0.000 claims description 7
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 6
- QGXLVXZRPRRCRP-IDIVVRGQSA-L Adenosine 5'-phosphate disodium Chemical compound [Na+].[Na+].C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP([O-])([O-])=O)[C@@H](O)[C@H]1O QGXLVXZRPRRCRP-IDIVVRGQSA-L 0.000 claims description 3
- 239000000243 solution Substances 0.000 description 20
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 10
- OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 description 10
- 230000001171 adenosinetriphosphoric effect Effects 0.000 description 9
- UNXRWKVEANCORM-UHFFFAOYSA-N triphosphoric acid Chemical compound OP(O)(=O)OP(O)(=O)OP(O)(O)=O UNXRWKVEANCORM-UHFFFAOYSA-N 0.000 description 9
- 229940048102 triphosphoric acid Drugs 0.000 description 9
- 150000003839 salts Chemical class 0.000 description 7
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 6
- 239000002126 C01EB10 - Adenosine Substances 0.000 description 5
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 5
- 229960005305 adenosine Drugs 0.000 description 5
- 210000003205 muscle Anatomy 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- GFFGJBXGBJISGV-UHFFFAOYSA-N Adenine Chemical compound NC1=NC=NC2=C1N=CN2 GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 description 2
- 229930024421 Adenine Natural products 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- 229960000643 adenine Drugs 0.000 description 2
- 239000003708 ampul Substances 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 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 description 1
- BAWFJGJZGIEFAR-NNYOXOHSSA-N NAD zwitterion Chemical compound NC(=O)C1=CC=C[N+]([C@H]2[C@@H]([C@H](O)[C@@H](COP([O-])(=O)OP(O)(=O)OC[C@@H]3[C@H]([C@@H](O)[C@@H](O3)N3C4=NC=NC(N)=C4N=C3)O)O2)O)=C1 BAWFJGJZGIEFAR-NNYOXOHSSA-N 0.000 description 1
- 208000003251 Pruritus Diseases 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 239000000370 acceptor Substances 0.000 description 1
- 150000003838 adenosines Chemical class 0.000 description 1
- PYMYPHUHKUWMLA-LMVFSUKVSA-N aldehydo-D-ribose Chemical compound OC[C@@H](O)[C@@H](O)[C@@H](O)C=O PYMYPHUHKUWMLA-LMVFSUKVSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
- 229910001863 barium hydroxide Inorganic materials 0.000 description 1
- 159000000009 barium salts Chemical class 0.000 description 1
- WAKZZMMCDILMEF-UHFFFAOYSA-H barium(2+);diphosphate Chemical compound [Ba+2].[Ba+2].[Ba+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O WAKZZMMCDILMEF-UHFFFAOYSA-H 0.000 description 1
- 239000003637 basic solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000004159 blood analysis Methods 0.000 description 1
- 230000023852 carbohydrate metabolic process Effects 0.000 description 1
- 235000021256 carbohydrate metabolism Nutrition 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002972 pentoses Chemical class 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
- C07H1/02—Phosphorylation
Definitions
- This invention relates to alkali metal salts of adenylic acid.
- adenylic acid system includes a series of rather complicated compounds which are combinations of the base adenine '(G-amino purine), the pentose d-ribose, and phosphoric acid, among others.
- the combination of adenine with ribos linked in glycosidic union at the 9- position of the base constitutes the substance known as adenosine, which has the following formula:
- the adenylic acid system in the body appears to constitute a mobile equilibrium which functions as a carrier for phosphoric acid, and is is desig- 2 essential to carbohydrate metabolism.
- the lower phosphate esters of adenosine act as phosphoric acid acceptors, and the more highly phosphorylated derivatives act as donators of the acid.
- muscle contains adenosine tri+phosphoric acid.
- Adenylic acid as such is not contained in animal tissue.
- the alkali metal salts of adenosine tri-phosphoric acid have been proposed for therapeutical purposes (U. S. Patent No. 1,978,881), and that adenylic acid as such, both from yeast and muscle sources, has been prepared, as well as adenosine tri-phosphoric acid and the alkali metal salts of the latter as referred to above.
- an alkali met'al salt of adenylic acid is advantageousfor therapeutic administration.
- the body does not contain adenylic acid, it is believed to use this as a source for the formation of the muscle component, namely adenosine tri-phosphoric acid.
- the adenylic acid When administered as the alkali metal adenylate, the adenylic acid is utilized in a slow and steady way and therefore is capable of giving a more sustained effect than is possible with the administration of adenosine tri-phosphoric acid or its alkali metal salts.
- the alkali metal salts of adenyllc acid are exceptionally stable as contrasted with the adenosine tri-phosphoric acid and its salts.
- the sodium salts of the latter decompose in time even when maintained in a normally dry state.
- the alkali metal salts of adenylic acid are remarkably stable, not only in a dry state but even in solution. The latter property permits the alkali metal salts of adenylic acid to be packaged in aqueous solution in sterilized 'ampule form for intra-muscular administration, with the knowledge that the activity will not deteriorate upon storage of the solution.
- alkali metal salts of adenylic acid in the dry form are ex-'- tremely soluble as compared with the salts here'- to'fo're known, and may be administered orally during which time they can be absorbed through I the fmucou's membrane.
- alkalimetal salts of adenylic acid may be prepared from the adenosine tri-phospho'ric acid naturally occurring in muscle or from yeast in accordance with known hydrolysis and separation techniques.
- adenosine in a buffered phosphate solution may be reacted with yeast or a yeast plasmolysate to produce adenosine triphosphoric acid and cozymase in addition to adenylic acid.
- yeast or a yeast plasmolysate may be reacted with yeast or a yeast plasmolysate to produce adenosine triphosphoric acid and cozymase in addition to adenylic acid.
- yeast or plasmolysate may be subjected to hydrolysis as described in U. S. Patent No. 2,174,475.
- the adenylic acid is then neutralized with sodium hydroxide, potassium hydroxide or an equivalent base.
- the solution may be placed in ampules and sterilized since the adenylate alkali metal salt is stable at the high temperatures used in sterilization. Alternatively the solution may be evaporated to dryness and sodium adenylate separated as a white crystalline material. Reference to the salt contemplates it in solution or crystalline form.
- the adenylate salt can exist as either a monoor disalt form depending upon the replacement by the metal of one or both of the hydrogens of the hydroxyl groups present in the terminal phosphoric acid radical.
- Example I 1 millimol (0.347 grams) of adenylic acid (adenosine-5-monophosphoric acid) was suspended in 10 cc. of distilled water and 1 millimol (0.04 grams) of sodium hydroxide was added in the form of a 4% solution. The mixture immediately becomes a clear solution. 35 cc. of acetone was added to the solution and a granular white solid precipitated which was filtered and washed with acetone. Upon drying the product was found to be mono-sodium adenylate. It was a white crystalline solid which decomposed at a high temperature before it melted. A solution of 20 mg. per cc. of water had a pH of 5.55.
- adenylic acid adenosine-5-monophosphoric acid
- Example I 1 millimol (0347 grams) of adenylic acid (adenosine-5-monophosphoric acid) was suspended in 10 cc. of distilled water and 2 millimols (0.08 grams of sodium hydroxide was added in the form of a 4% solution. The mixture immediately becomes a clear solution. 35 cc. of acetone was added to the solution and a granular white solid precipitated which was filtered and washed with acetone. Upon drying the product was found to be di-sodium adenylate. It was a white crystalline solid which decomposed at a high temperature before it melted. A solution of 20 mg. per cc. of water had a pH of 11.0.
- Example III The procedure described in the previous two examples was repeated except that the amount of the sodium hydroxide solution added was such that the pH of the solution was 6.5 This required 0.05 grams of sodium hydroxide. A portion of the aqueous solution was placed in am pules of 1 cc. each and sterilized. When the salt is to be packed in an aqueous solution, it is preferred that the pH be between 6 and 7 as this range is best suited for intra-muscular injection. Within this range the solution will contain both salts, the major portion being the mono-sodium salt.
- the new compounds of my invention are suitable for treatment where blood analysis indicates an insuflicient amount of the nucleic phosphorus compounds. Notable results have been obtained in the treatment of pruritis.
- said solution having a pH of between 5.55 and 7.
- said solution having a pH of between 6 and 7.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Patented Sept. 29, 1953 UNITED STATES PATENT OFFICE 2,653,897 i ALKALI METAL. SALTS OFADENYLIC ACID Edward K. Harvill, Essex, Conn., assignor to Ernst Bischofl Company, Inc., Ivoryt'on, Conn.,
a corporation of Connecticut No Drawing. Application June 10, 1949, Serial No. 98,406
2 Claims.
This invention relates to alkali metal salts of adenylic acid.
The so-called adenylic acid system includes a series of rather complicated compounds which are combinations of the base adenine '(G-amino purine), the pentose d-ribose, and phosphoric acid, among others. The combination of adenine with ribos linked in glycosidic union at the 9- position of the base constitutes the substance known as adenosine, which has the following formula:
| H The mono-phosphoric derivative of adenosine (adenosine--mono-phosphoric acid) I hated herein as adenylic acid. It has the following formula:
Some references give other formulas, but the above formula represents the best current information on the structure of the compound.
The adenylic acid system in the body appears to constitute a mobile equilibrium which functions as a carrier for phosphoric acid, and is is desig- 2 essential to carbohydrate metabolism. The lower phosphate esters of adenosine act as phosphoric acid acceptors, and the more highly phosphorylated derivatives act as donators of the acid.
It is known that muscle contains adenosine tri+phosphoric acid. Adenylic acid as such is not contained in animal tissue. I am aware that the alkali metal salts of adenosine tri-phosphoric acid have been proposed for therapeutical purposes (U. S. Patent No. 1,978,881), and that adenylic acid as such, both from yeast and muscle sources, has been prepared, as well as adenosine tri-phosphoric acid and the alkali metal salts of the latter as referred to above. c
I have discoveredthat an alkali met'al salt of adenylic acid is advantageousfor therapeutic administration. Although the body does not contain adenylic acid, it is believed to use this as a source for the formation of the muscle component, namely adenosine tri-phosphoric acid. When administered as the alkali metal adenylate, the adenylic acid is utilized in a slow and steady way and therefore is capable of giving a more sustained effect than is possible with the administration of adenosine tri-phosphoric acid or its alkali metal salts.
Furthermore, the alkali metal salts of adenyllc acid are exceptionally stable as contrasted with the adenosine tri-phosphoric acid and its salts. The sodium salts of the latter decompose in time even when maintained in a normally dry state. In contrast, the alkali metal salts of adenylic acid are remarkably stable, not only in a dry state but even in solution. The latter property permits the alkali metal salts of adenylic acid to be packaged in aqueous solution in sterilized 'ampule form for intra-muscular administration, with the knowledge that the activity will not deteriorate upon storage of the solution. c
The alkali metal salts of adenylic acid in the dry form, in addition to being stable, are ex-'- tremely soluble as compared with the salts here'- to'fo're known, and may be administered orally during which time they can be absorbed through I the fmucou's membrane. r
The alkalimetal salts of adenylic acid may be prepared from the adenosine tri-phospho'ric acid naturally occurring in muscle or from yeast in accordance with known hydrolysis and separation techniques. U I
For example, adenosine in a buffered phosphate solution may be reacted with yeast or a yeast plasmolysate to produce adenosine triphosphoric acid and cozymase in addition to adenylic acid. In order to convert the higher phosphoric acid compounds into the adenylic acid they may be subjected to hydrolysis as described in U. S. Patent No. 2,174,475.
Another method for the preparation of adenylic acid from adenosine tri-phosphoric acid obtained from yeast is described in U. S. Patent No. 1,976,175. Preparation of adenylic acid from adenosine tri-phosphoric acid from muscle is described in U. S. Patent No. 1,977,525.
In general all of these processes precipitate the adenosine tri-phosphoric acid with an alkaline earth metal base such as barium hydroxide which is hydrolyzed in an appropriate basic solution. The second or third phosphate radicals split oif during hydrolysis and are precipitated as barium phosphate leaving the barium salt of adenylic acid in solution. The latter is then precipitated as the lead salt and the lead removed as a sulfide or sulfate to leave the adenylic acid in solut on.
In accordance with my invention, the adenylic acid is then neutralized with sodium hydroxide, potassium hydroxide or an equivalent base. The solution may be placed in ampules and sterilized since the adenylate alkali metal salt is stable at the high temperatures used in sterilization. Alternatively the solution may be evaporated to dryness and sodium adenylate separated as a white crystalline material. Reference to the salt contemplates it in solution or crystalline form.
It will be appreciated that the adenylate salt can exist as either a monoor disalt form depending upon the replacement by the metal of one or both of the hydrogens of the hydroxyl groups present in the terminal phosphoric acid radical.
Example I 1 millimol (0.347 grams) of adenylic acid (adenosine-5-monophosphoric acid) was suspended in 10 cc. of distilled water and 1 millimol (0.04 grams) of sodium hydroxide was added in the form of a 4% solution. The mixture immediately becomes a clear solution. 35 cc. of acetone was added to the solution and a granular white solid precipitated which was filtered and washed with acetone. Upon drying the product was found to be mono-sodium adenylate. It was a white crystalline solid which decomposed at a high temperature before it melted. A solution of 20 mg. per cc. of water had a pH of 5.55.
Example I! 1 millimol (0347 grams) of adenylic acid (adenosine-5-monophosphoric acid) was suspended in 10 cc. of distilled water and 2 millimols (0.08 grams of sodium hydroxide was added in the form of a 4% solution. The mixture immediately becomes a clear solution. 35 cc. of acetone was added to the solution and a granular white solid precipitated which was filtered and washed with acetone. Upon drying the product was found to be di-sodium adenylate. It was a white crystalline solid which decomposed at a high temperature before it melted. A solution of 20 mg. per cc. of water had a pH of 11.0.
Example III The procedure described in the previous two examples was repeated except that the amount of the sodium hydroxide solution added was such that the pH of the solution was 6.5 This required 0.05 grams of sodium hydroxide. A portion of the aqueous solution was placed in am pules of 1 cc. each and sterilized. When the salt is to be packed in an aqueous solution, it is preferred that the pH be between 6 and 7 as this range is best suited for intra-muscular injection. Within this range the solution will contain both salts, the major portion being the mono-sodium salt.
Another portion of the aqueous solution was treated with acetone as in the previous examples to yield a white crystalline solid the major portion of which was the mono-sodium adenylate and the minor portion of which was the di-sodium adenylate.
The new compounds of my invention are suitable for treatment where blood analysis indicates an insuflicient amount of the nucleic phosphorus compounds. Notable results have been obtained in the treatment of pruritis.
I claim:
1. A stable sterile aqueous solution of a major proportion of monosodium adenylate and a minor proportion of disodium adenylate derived from an adenylic acid having the formula:
said solution having a pH of between 5.55 and 7.
z. A sterile aqueous solution of a major proportion of monosodium adenylate and a minor proportion of disodium adenylate derived from an adenylic acid having the formula:
said solution having a pH of between 6 and 7.
EDWARD K. HARVILL.
References Cited in the file of this patent UNITED STATES PATENTS OTHER REFERENCES E. Lehnartz-Chemical Abstracts, volume 23,
F page 3692, (1929).
LutwakMann Biochemical Journal, Cambridge 1936, pages 1405 to 1412.
Frankel Die Arzneimittel Synthese, J. Springer,
1927, Berlin, page 222.
Claims (1)
1. A STABLE STERILE AQUEOUS SOLUTION OF A MAJOR PROPORTION OF MONOSODIUM ADENYLATE AND A MINOR PROPORTION OF DISODIUM ADENYLATE DERIVED FROM AN ADENYLIC ACID HAVING THE FORMULA:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US98406A US2653897A (en) | 1949-06-10 | 1949-06-10 | Alkali metal salts of adenylic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US98406A US2653897A (en) | 1949-06-10 | 1949-06-10 | Alkali metal salts of adenylic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2653897A true US2653897A (en) | 1953-09-29 |
Family
ID=22269138
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US98406A Expired - Lifetime US2653897A (en) | 1949-06-10 | 1949-06-10 | Alkali metal salts of adenylic acid |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2653897A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3190877A (en) * | 1962-02-15 | 1965-06-22 | Takeda Chemical Industries Ltd | Crystalline sodium salt of 5'-guanylic acid and a method for preparing the same |
| DE1226588B (en) * | 1961-08-17 | 1966-10-13 | Takeda Chemical Industries Ltd | Process for the enrichment of purine nucleoside 5'-monophosphates |
| US20050054615A1 (en) * | 2002-11-07 | 2005-03-10 | Rensselaer Polytechnic Institute | Calmodulin independent activation of nitric oxide synthase |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1976175A (en) * | 1931-02-23 | 1934-10-09 | Winthrop Chem Co Inc | Process of preparing adenosine phosphoric acid |
| US1978881A (en) * | 1932-02-27 | 1934-10-30 | Winthrop Chem Co Inc | Alkali salts of adenyl-pyrophosphoric acids |
| US2082395A (en) * | 1933-07-21 | 1937-06-01 | Soc Of Chemical Ind | Esters of nucleotides and process of making same |
| US2101099A (en) * | 1932-12-27 | 1937-12-07 | Frances R Ruskin | Manganese compounds of nucleotides and of their hydrolytic decomposition products |
| US2215233A (en) * | 1937-11-13 | 1940-09-17 | Simon L Ruskin | Iron compound of nucleotides and their organic hydrolytic decomposition products and method of making same |
| US2379914A (en) * | 1942-08-14 | 1945-07-10 | Schwarz Lab Inc | Recovery of rare sugars |
| US2417841A (en) * | 1944-06-21 | 1947-03-25 | Frances R Ruskin | Nucleotide compounds of components of vitamin b complex |
-
1949
- 1949-06-10 US US98406A patent/US2653897A/en not_active Expired - Lifetime
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1976175A (en) * | 1931-02-23 | 1934-10-09 | Winthrop Chem Co Inc | Process of preparing adenosine phosphoric acid |
| US1978881A (en) * | 1932-02-27 | 1934-10-30 | Winthrop Chem Co Inc | Alkali salts of adenyl-pyrophosphoric acids |
| US2101099A (en) * | 1932-12-27 | 1937-12-07 | Frances R Ruskin | Manganese compounds of nucleotides and of their hydrolytic decomposition products |
| US2082395A (en) * | 1933-07-21 | 1937-06-01 | Soc Of Chemical Ind | Esters of nucleotides and process of making same |
| US2215233A (en) * | 1937-11-13 | 1940-09-17 | Simon L Ruskin | Iron compound of nucleotides and their organic hydrolytic decomposition products and method of making same |
| US2379914A (en) * | 1942-08-14 | 1945-07-10 | Schwarz Lab Inc | Recovery of rare sugars |
| US2417841A (en) * | 1944-06-21 | 1947-03-25 | Frances R Ruskin | Nucleotide compounds of components of vitamin b complex |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1226588B (en) * | 1961-08-17 | 1966-10-13 | Takeda Chemical Industries Ltd | Process for the enrichment of purine nucleoside 5'-monophosphates |
| US3190877A (en) * | 1962-02-15 | 1965-06-22 | Takeda Chemical Industries Ltd | Crystalline sodium salt of 5'-guanylic acid and a method for preparing the same |
| US20050054615A1 (en) * | 2002-11-07 | 2005-03-10 | Rensselaer Polytechnic Institute | Calmodulin independent activation of nitric oxide synthase |
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