US3418325A - Method of producing a product between meso-inositol and nicotinic acid - Google Patents
Method of producing a product between meso-inositol and nicotinic acid Download PDFInfo
- Publication number
- US3418325A US3418325A US516744A US51674465A US3418325A US 3418325 A US3418325 A US 3418325A US 516744 A US516744 A US 516744A US 51674465 A US51674465 A US 51674465A US 3418325 A US3418325 A US 3418325A
- Authority
- US
- United States
- Prior art keywords
- nicotinic acid
- meso
- inositol
- product
- producing
- 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 - Lifetime
Links
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 title description 48
- 229960003512 nicotinic acid Drugs 0.000 title description 23
- 235000001968 nicotinic acid Nutrition 0.000 title description 23
- 239000011664 nicotinic acid Substances 0.000 title description 23
- 229960000367 inositol Drugs 0.000 title description 6
- CDAISMWEOUEBRE-GPIVLXJGSA-N inositol Chemical compound O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@@H]1O CDAISMWEOUEBRE-GPIVLXJGSA-N 0.000 title description 5
- CDAISMWEOUEBRE-UHFFFAOYSA-N scyllo-inosotol Natural products OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 title description 5
- 238000000034 method Methods 0.000 title description 3
- MFZCIDXOLLEMOO-UHFFFAOYSA-N inositol hexanicotinate Chemical compound C=1C=CN=CC=1C(=O)OC(C(C(OC(=O)C=1C=NC=CC=1)C(OC(=O)C=1C=NC=CC=1)C1OC(=O)C=2C=NC=CC=2)OC(=O)C=2C=NC=CC=2)C1OC(=O)C1=CC=CN=C1 MFZCIDXOLLEMOO-UHFFFAOYSA-N 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 239000000243 solution Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 description 4
- 239000011707 mineral Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000008280 blood Substances 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 238000011010 flushing procedure Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000036765 blood level Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000005484 gravity Effects 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 239000002207 metabolite Substances 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 230000001575 pathological effect Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 241000282414 Homo sapiens Species 0.000 description 1
- WWNNZCOKKKDOPX-UHFFFAOYSA-N N-methylnicotinate Chemical compound C[N+]1=CC=CC(C([O-])=O)=C1 WWNNZCOKKKDOPX-UHFFFAOYSA-N 0.000 description 1
- BIMKYWNFAXOBEQ-UHFFFAOYSA-N [2-hydroxy-3,4,5,6-tetrakis(pyridine-3-carbonyloxy)cyclohexyl] pyridine-3-carboxylate Chemical compound C=1C=CN=CC=1C(=O)OC1C(OC(=O)C=2C=NC=CC=2)C(OC(=O)C=2C=NC=CC=2)C(OC(=O)C=2C=NC=CC=2)C(O)C1OC(=O)C1=CC=CN=C1 BIMKYWNFAXOBEQ-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 230000007012 clinical effect Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 229940035564 duration Drugs 0.000 description 1
- 230000037149 energy metabolism Effects 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 238000005245 sintering Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 230000000304 vasodilatating effect Effects 0.000 description 1
- 235000019156 vitamin B Nutrition 0.000 description 1
- 239000011720 vitamin B Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/80—Acids; Esters in position 3
Definitions
- the present invention relates to a method of producing a product between mesq-inositol and nicotinic acid.
- Nicotinic acid is a component in the B-vitamin complex and has proved to be of considerable biochemical significance in different biological systems.
- nicotinic acid has a directly vasodilating effect and is, among other things, of considerable significance to the metabolism of fats and carbohydrates. Nicotinic acid also influences the cholesterol synthes's in a negative direction.
- Different nicotinic acid compounds can have the same effect as nicotinic acid in proportion to their capability of generating nicotinic acid and active nicotinic acid metabolites. There can be considerable difierences in this respect.
- meso-ino sitol hexanicotinate which has thereby also become widely used clinically. Owing to its symmetrical constitution and comparatively high molecular weight, this compound has the property that it can be successively hydrolyzed and/or resorbed in vivo, and a continuously raised nicotinic acid level in the blood then occurs. This gives improved metabolic conditions when there are pathological disturbances of the energy metabolism in living tissue.
- the purpose of the present invention is to make better use of an ester of the type meso-inositol hexanicotinate, which has been introduced.
- Extensive investigations have shown that if, by means of a mineral acid or a strong organic acid, the meso-inositol hexanicotinate is hydrolyzed to such an extent that with removed side chains of nicotinic acid derivates, a nitrogen content of approx. and a melting point within the interval of 120130 3,418,325 Patented Dec. 24, 1968 ICC C. is obtained, the nicotinic acid preparation obtained, when used, will cause a resorption, in the patients checked, of no less than In spite of the improved resorption, the disadvantage of the flushing effect and prickliness does not occur.
- the reason for the improved resorption must be that if a nicotinic acid preparation of the type meso-inositol hexanicotinate is used, the nicotinic acid is secreted from this preparation more easily when a side chain has been removed from the beginning.
- Example 1 810 g. of meso-inositol hexanicotinate is dissolved in 8 litres of Water and approx. 600 g. of hydrochloric acid, specific gravity 1.19, to a pH of approx. 1.
- the solution is treated at a temperature of approx. 20 C. for 40 hours through slow stirring.
- the solution is carbon treated with an addition of versinate for complex binding of any heavy metal ions, filtered and neutralized with a 25% solution of ammonia, bicarbonate, carbonate or some other appropriate alkali solution, until a pH of at least 6.5 has been reached.
- the reaction product is then precipitated, and is filtered oil? and washed with water.
- the product obtained, after drying, has shown beginning sintering at l43145 C., and an equivalent weight of 141.8 and a nitrogen content of 9.95%.
- the yield was 91% of the theoretical yield.
- Part of the hydrolyzed nicotinic acid can be recovered from the mother liquid, through evaporation and adjustment of the pH to 3.5, which is the isoelectric point of the nicotinic acid.
- Example 2 810 g. of meso-inositol hexanicotinate is dissolved in 8 litres of Water and approx. 300 g. of sulfuric acid, specific gravity 1.84, to a pH of 1.1. After 40 hours of treatment at approx. 20 C., the reaction product is worked up as per Example 1, and the same yield and data is then obtained.
- An ester of meso-inositol and nicotinic acid having a nitrogen content of about 10.0% and a melting point of about 130 C. which is prepared by stirring mesoinositol hexanicotinate in an aqueous solution containing a mineral acid or a strong organic acid at a temperature of about 20 C. for a period of about 40 hours and bringing the solution to a pH of about 6.5 to precipitate the product.
Description
United States Patent 3,418,325 METHOD OF PRODUCING A PRODUCT BETWEEN MESO-INOSITOL AND NICOTINIC ACID Bo Thuresson af Ekenstam, Molndal, and Bror Giista Pettersson, Karlskoga, Sweden, assignors to Aktiebolaget Bofors, Bofors, Sweden No Drawing. Filed Dec. 27, 1965, Ser. No. 516,744 3 Claims. (Cl. 260295.5)
ABSTRACT OF THE DISCLOSURE Meso-inositol pentanicotinate is prepared by the controlled hydrolysis of meso-inositol hexanicotinate in acidic aqueous solution. The new compound exhibits the same desirable pharmacological properties of the hexanicotinate with a considerable reduction in such undesirable side effects as flushing and prickliness.
The present invention relates to a method of producing a product between mesq-inositol and nicotinic acid. Nicotinic acid is a component in the B-vitamin complex and has proved to be of considerable biochemical significance in different biological systems. Moreover, nicotinic acid has a directly vasodilating effect and is, among other things, of considerable significance to the metabolism of fats and carbohydrates. Nicotinic acid also influences the cholesterol synthes's in a negative direction. Different nicotinic acid compounds can have the same effect as nicotinic acid in proportion to their capability of generating nicotinic acid and active nicotinic acid metabolites. There can be considerable difierences in this respect. In order to obtain a clinical effect under pathological conditions, a continuously satisfactory blood level is of great importance. It is known that merely moderate doses of nicotinic acid gives a very high blood level, of short dura tion, followed by a rapid secretion of different metabolites, primarily in the form of N-methyl nicotinic acid. The eflFect of this high, transient content of nicotinic acid in the blood involves considerable side effects in the form of heavy flushing and heat, with prickliness in the skin. Many esters of nicotinic acid give the same rapid resorption and side effects as the nicotinic acid itself, and are, consequently, not clinically unobjectionable pharmaceuticals. An ester which does not have these side effects is meso-ino sitol hexanicotinate, which has thereby also become widely used clinically. Owing to its symmetrical constitution and comparatively high molecular weight, this compound has the property that it can be successively hydrolyzed and/or resorbed in vivo, and a continuously raised nicotinic acid level in the blood then occurs. This gives improved metabolic conditions when there are pathological disturbances of the energy metabolism in living tissue. By means of resorption investigations on human beings, it has been possible to determine that the meso-inositol hexanicotinate is not totally resorbed when passing through the alimentary canal, even if a significant rise of the nicotinic acid level in the blood and the metabolite in the urine takes place. The resorption in patients which have been checked was approx. 75%
The purpose of the present invention is to make better use of an ester of the type meso-inositol hexanicotinate, which has been introduced. Extensive investigations have shown that if, by means of a mineral acid or a strong organic acid, the meso-inositol hexanicotinate is hydrolyzed to such an extent that with removed side chains of nicotinic acid derivates, a nitrogen content of approx. and a melting point within the interval of 120130 3,418,325 Patented Dec. 24, 1968 ICC C. is obtained, the nicotinic acid preparation obtained, when used, will cause a resorption, in the patients checked, of no less than In spite of the improved resorption, the disadvantage of the flushing effect and prickliness does not occur.
The reason for the improved resorption must be that if a nicotinic acid preparation of the type meso-inositol hexanicotinate is used, the nicotinic acid is secreted from this preparation more easily when a side chain has been removed from the beginning.
The invention will be described in more detail in the following examples:
Example 1 810 g. of meso-inositol hexanicotinate is dissolved in 8 litres of Water and approx. 600 g. of hydrochloric acid, specific gravity 1.19, to a pH of approx. 1. The solution is treated at a temperature of approx. 20 C. for 40 hours through slow stirring. When the reaction time is over, the solution is carbon treated with an addition of versinate for complex binding of any heavy metal ions, filtered and neutralized with a 25% solution of ammonia, bicarbonate, carbonate or some other appropriate alkali solution, until a pH of at least 6.5 has been reached. The reaction product is then precipitated, and is filtered oil? and washed with water. The product obtained, after drying, has shown beginning sintering at l43145 C., and an equivalent weight of 141.8 and a nitrogen content of 9.95%. The yield was 91% of the theoretical yield. Part of the hydrolyzed nicotinic acid can be recovered from the mother liquid, through evaporation and adjustment of the pH to 3.5, which is the isoelectric point of the nicotinic acid.
Example 2 810 g. of meso-inositol hexanicotinate is dissolved in 8 litres of Water and approx. 300 g. of sulfuric acid, specific gravity 1.84, to a pH of 1.1. After 40 hours of treatment at approx. 20 C., the reaction product is worked up as per Example 1, and the same yield and data is then obtained.
We claim:
1. An ester of meso-inositol and nicotinic acid having a nitrogen content of about 10.0% and a melting point of about 130 C. which is prepared by stirring mesoinositol hexanicotinate in an aqueous solution containing a mineral acid or a strong organic acid at a temperature of about 20 C. for a period of about 40 hours and bringing the solution to a pH of about 6.5 to precipitate the product.
2. An ester of meso-inositol and nicotinic acid according to claim 1, wherein the mineral acid is hydrochloric acid.
3. An ester of meso-inositol and nicotinic acid according to claim 1, wherein the mineral acid is sulfuric acid.
References Cited Badgett et al.: I. Am. Chem. Soc., vol. 69, p. 2907 (1949).
Donatelli et al.: Chem. Abstracts I, vol. 49, 1956, par. 3390b and 3391a.
Seckfort et al.: Chem. Abstracts II, vol. 54, par. 25, 270 1960).
HENRY R. JILES, Primary Examiner.
A. L. ROTMAN, Assistant Examiner.
U.S. Cl. X.R. 16765
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US516744A US3418325A (en) | 1965-12-23 | 1965-12-27 | Method of producing a product between meso-inositol and nicotinic acid |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEA0051172 | 1965-12-23 | ||
| US516744A US3418325A (en) | 1965-12-23 | 1965-12-27 | Method of producing a product between meso-inositol and nicotinic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3418325A true US3418325A (en) | 1968-12-24 |
Family
ID=25964272
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US516744A Expired - Lifetime US3418325A (en) | 1965-12-23 | 1965-12-27 | Method of producing a product between meso-inositol and nicotinic acid |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US3418325A (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4757053A (en) * | 1981-08-03 | 1988-07-12 | Fidia, S.P.A. | Pyridinecarboxamide or trimethoxybenzamide compounds derived from nitrogenous lipids, pharmaceutical compositions containing same which possess anti-convalsive and anti-epileptic properties |
| CN105153025A (en) * | 2015-09-23 | 2015-12-16 | 潍坊盛瑜药业有限公司 | Inositol nicotinate polymorph A and preparing method thereof |
| US10175355B2 (en) | 2014-10-22 | 2019-01-08 | Denso Corporation | Object detection apparatus |
| US10175354B2 (en) | 2014-10-22 | 2019-01-08 | Denso Corporation | Object detection apparatus |
| US10436900B2 (en) | 2014-10-22 | 2019-10-08 | Denso Corporation | Object detection apparatus |
| US10453343B2 (en) | 2014-10-22 | 2019-10-22 | Denso Corporation | Object detection apparatus |
| US10578736B2 (en) | 2014-10-22 | 2020-03-03 | Denso Corporation | Object detection apparatus |
-
1965
- 1965-12-27 US US516744A patent/US3418325A/en not_active Expired - Lifetime
Non-Patent Citations (1)
| Title |
|---|
| None * |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4757053A (en) * | 1981-08-03 | 1988-07-12 | Fidia, S.P.A. | Pyridinecarboxamide or trimethoxybenzamide compounds derived from nitrogenous lipids, pharmaceutical compositions containing same which possess anti-convalsive and anti-epileptic properties |
| US10175355B2 (en) | 2014-10-22 | 2019-01-08 | Denso Corporation | Object detection apparatus |
| US10175354B2 (en) | 2014-10-22 | 2019-01-08 | Denso Corporation | Object detection apparatus |
| US10436900B2 (en) | 2014-10-22 | 2019-10-08 | Denso Corporation | Object detection apparatus |
| US10453343B2 (en) | 2014-10-22 | 2019-10-22 | Denso Corporation | Object detection apparatus |
| US10578736B2 (en) | 2014-10-22 | 2020-03-03 | Denso Corporation | Object detection apparatus |
| CN105153025A (en) * | 2015-09-23 | 2015-12-16 | 潍坊盛瑜药业有限公司 | Inositol nicotinate polymorph A and preparing method thereof |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Copeland et al. | The preparation and reactions of 2-benzimidazolecarboxylic acid and 2-benzimidazoleacetic acid | |
| DE2845496A1 (en) | N HIGH 2 -SUBSTITUTED PHENYL-2,6- DIAMINONEBULARINE AND MEDICINAL PREPARATIONS CONTAINING THEM | |
| JPH01308292A (en) | Production of ganglioside derivative | |
| US3418325A (en) | Method of producing a product between meso-inositol and nicotinic acid | |
| DE3873870D1 (en) | ANDROSTAN-17-CARBONIC ACID ESTER, METHOD FOR THE PRODUCTION THEREOF AND MEDICINAL PRODUCTS CONTAINING IT. | |
| CH486487A (en) | Process for the preparation of disubstituted adenosine derivatives | |
| SU612636A3 (en) | Method of obtaining d-homosteroids | |
| EP0621037B1 (en) | Pyrido-pyrimidinediones, process for their preparation and their use as pharmaceuticals | |
| EP0353668A2 (en) | Process for the preparation of N,N-bis(alkoxyalkyl) diamides of pyridine-2,4-dicarboxylic acid | |
| Easty | The Synthesis and Acid Hydrolysis of Methyl α-D-Glucopyranosiduronic Acid1 | |
| US2955115A (en) | Long-chain fatty acid esters of vitamin b6 | |
| DE1966640B2 (en) | PROCESS FOR PREPARING 4-HYDROXY- AND 4,6-DIHYDROXY-PYRAZOLO SQUARE CLAMP TO 3,4-D SQUARE CLAMP TO PYRIMIDINES | |
| DE1910930A1 (en) | Process for the production of new 1,6-dimethyl-10alpha-ergoline derivatives | |
| DE10015525A1 (en) | Synthetic derivatives of lunular acid, medicaments containing this compound, process for the preparation of lunular acid derivatives and their use | |
| CH366523A (en) | Process for the production of the new 1,3,4,6- and 1,3,4,5-tetranicotinoyl-fructose | |
| CA1138866A (en) | Chemical process for preparing isoxazolo-benzoxazinone derivatives | |
| US2863873A (en) | Esters of nicotinic acid | |
| US2816896A (en) | Process for the production of 2, 3, 5, 6 tetrahydro-1-imidaz (1, 2-a) imidazole | |
| SU476265A1 (en) | The method of obtaining 0 "monophosphates of 6-substituted 9- (-dioxyalkyl-2) purines | |
| CH629806A5 (en) | Process for the preparation of substituted purines | |
| CH251023A (en) | Process for the preparation of B-picolyl nicotinate. | |
| US4224323A (en) | Method for lowering serum uric acid | |
| CH251026A (en) | Process for the preparation of B-picolyl nicotinate. | |
| DE1670539C3 (en) | Diacylthiamines and processes for their preparation | |
| AT273964B (en) | Process for the preparation of new benzheterocyclic compounds and their salts |