US2947741A - Isobebeerine nicotinate - Google Patents
Isobebeerine nicotinate Download PDFInfo
- Publication number
- US2947741A US2947741A US780952A US78095258A US2947741A US 2947741 A US2947741 A US 2947741A US 780952 A US780952 A US 780952A US 78095258 A US78095258 A US 78095258A US 2947741 A US2947741 A US 2947741A
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- US
- United States
- Prior art keywords
- isobebeerine
- pyridine
- nicotinate
- salt
- carboxylic acid
- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
- C07D491/18—Bridged systems
Definitions
- This invention relates to a new and usefulv improvement in antispasmodic compositions.
- the particular group of antispasmodic compositions herein described is characterized by isobebeerine nicotinate.
- the purpose of this invention is to provide a new and useful composition for safe and efiective antispasmodic activity.
- a further purpose of the invention described herein is to provide a process for the manufacture of the said antispasmodic composition.
- At least one other form involving a double nicotinate salt will be described.
- Isobebeerine sometimes called isochondodendrine, is an alkaloid. The empirical formula is: C 72.70%, H 6.44%, N 4.71%. The molecular weight is about 594.
- Isobebeerine is an extract derived from the root of chondodendron. It is purified by crystallization from alcohol. The melting point is approximately 290 C.
- Nicotinic acid consists of pyridine-S-carboxylic acid.
- the theory of the formation of the salt isobebeerine nicotinate is embodied in the following description. The description of the theory however, should not limit the invention in any manner and it is'not intended to do so. The following exposition is for the purpose of better understanding the art of manufacturing and using the invention as it appears in the specification and claims.
- the isobebeerine is a basic alkaloid, by reason of the two basic nitrogen atoms therein contained. These basic nitrogens react to form salts by reason of the group to which they belong. It is more common to form a single salt rather than a double salt by reason of the fact that one appears more basic than the other.
- Pyridine-3-carbocylic acid has ionization constant in the order of and the pH of an aqueous solution is approximately 2.7.
- the isomers of pyridine-3-carboxylic acid may have more acidity than pyridine-3carboxylic acid.
- the preferred embodiment of this invention utilizes pyridine- B-carboxylic acid.
- Example 1 Take 59 grams of isobebeerine alkaloid. Place in a mixing flask fitted with a mechanical stirrer. Add 12.3 grams of nicotinic acid. Both the alkaloid and the acid should be powdered and dry. Add 140 cc. of carbontetrachloride. The temperature is kept constant at approximately 17 C. While the reaction mixture is stirred for one-half hour. The stirring is not vigorous. The reaction mixture is then stoppered and placed in a refrigerator at 5 C. for six days. At the end of this time the solvent is evaporated and the reaction mixture is powdered. This may be added to lactose or any other pharmaceutical carrier for administration by mouth or parenterally.
- Example 2 Use 246 grams of nicotinic acid instead of the above amount.
- the product comprises substantially more isobebeerine as a dinicotinyl salt than is formed in the Example 3 40 grams each of isobebeerine alkaloid and nicotinic acid are used.
- the product consists of substantially more isobebeerine as a dinicotinate salt together alcohol in water.
- Example 4 Add 5.94 grams of isobebeerine to a 200 cc. flask fitted with a stirrer containing cc. of 50% ethyl Add 2.4 grams nicotinic acid. Stir vigorously for one hour. Evaporate the alcohol water mixture under reduced pressure.
- the above modification may be repeated with 1.25 grams nicotinic acid.
Description
United States Patent ISOBEBEERINE NICOTINATE Edgar A. Ferguson, Jr., 150 Woodrutf Ave., Brooklyn, N.Y.
No Drawing. Filed Dec. 17, 1958, Ser. No.780,952
3'Claims. (Cl. 260236) This invention relates to a new and usefulv improvement in antispasmodic compositions. The particular group of antispasmodic compositions herein described is characterized by isobebeerine nicotinate.
The purpose of this invention is to provide a new and useful composition for safe and efiective antispasmodic activity. A further purpose of the invention described herein is to provide a process for the manufacture of the said antispasmodic composition. At least one other form involving a double nicotinate salt will be described. Isobebeerine, sometimes called isochondodendrine, is an alkaloid. The empirical formula is: C 72.70%, H 6.44%, N 4.71%. The molecular weight is about 594. Isobebeerine is an extract derived from the root of chondodendron. It is purified by crystallization from alcohol. The melting point is approximately 290 C.
Nicotinic acid consists of pyridine-S-carboxylic acid. The theory of the formation of the salt isobebeerine nicotinate is embodied in the following description. The description of the theory however, should not limit the invention in any manner and it is'not intended to do so. The following exposition is for the purpose of better understanding the art of manufacturing and using the invention as it appears in the specification and claims. The isobebeerine is a basic alkaloid, by reason of the two basic nitrogen atoms therein contained. These basic nitrogens react to form salts by reason of the group to which they belong. It is more common to form a single salt rather than a double salt by reason of the fact that one appears more basic than the other. It has been found, however that in the formation of salts there are only certain acids which enhance or promote the antispasmodic action. One of these salts is pyridine -3-carboxylic acid. It has been found moreover that in the preparation of the salt only certain solvents are suitable from the standpoint of readily promoting the reaction and readily allowing purification after reaction has taken place. Some of these solvents are: chloroform, carbontetrachloride, and acetic anhydride. Of these the preferred solvent is carbontetrachloride. Isobebeerine alkaloid and pyridine- 3-carboxylic acid react mole for mole and also in a ratio of 2:1. What has been said for pyridine-S-carboxylic acid can also be said for its two isomers. Pyridine-3-carbocylic acid has ionization constant in the order of and the pH of an aqueous solution is approximately 2.7. By reason of the relationship of the carboxylic group to the nitrogen of the ring the isomers of pyridine-3-carboxylic acid may have more acidity than pyridine-3carboxylic acid. However the preferred embodiment of this invention utilizes pyridine- B-carboxylic acid.
The following example is meant to illustrate one of the preferred methods, among other methods, of manufacture. This example is not presented for any purpose of limiting the scope of the invention as delineated in above method.
Patented Aug. 2, 1960 Other methods Example 1 Take 59 grams of isobebeerine alkaloid. Place in a mixing flask fitted with a mechanical stirrer. Add 12.3 grams of nicotinic acid. Both the alkaloid and the acid should be powdered and dry. Add 140 cc. of carbontetrachloride. The temperature is kept constant at approximately 17 C. While the reaction mixture is stirred for one-half hour. The stirring is not vigorous. The reaction mixture is then stoppered and placed in a refrigerator at 5 C. for six days. At the end of this time the solvent is evaporated and the reaction mixture is powdered. This may be added to lactose or any other pharmaceutical carrier for administration by mouth or parenterally.
Example 2 Use 246 grams of nicotinic acid instead of the above amount. The product comprises substantially more isobebeerine as a dinicotinyl salt than is formed in the Example 3 40 grams each of isobebeerine alkaloid and nicotinic acid are used. When the method is applied to this proportion of ingredients the product consists of substantially more isobebeerine as a dinicotinate salt together alcohol in water.
with a larger excess of nicotinic acid than is obtained in the first alternate method.
Example 4 Add 5.94 grams of isobebeerine to a 200 cc. flask fitted with a stirrer containing cc. of 50% ethyl Add 2.4 grams nicotinic acid. Stir vigorously for one hour. Evaporate the alcohol water mixture under reduced pressure.
The above modification may be repeated with 1.25 grams nicotinic acid.
ExampleS Whenever carbon tetrachloride is used, acetic anhydride or chloroform may be used instead, with similar results. 1
Without further analysis, the foregoing will so fully reveal the gist of the present invention that others can by applying current knowledge readily adapt it for various applications without omitting features that, from the standpoint of prior art, fairly constitute essential characteristics of the generic or specific aspects of this invention and, therefore, such adaptations should and are intended to be comprehended within the meaning and range of equivalence of the following claims.
What is claimed as new and desired to be secured by Letters Patent is:
1. The salt of isobebeerine and an acid selected from the group consisting of pyridine-Z-carboxylic acid and pyridine-3-carboxylic acid.
2. The salt of 1 mol of isobebeerine and 1 mol of pyridine-S-carboxylic acid.
3. The salt of 1 mol of isobebeerine and 2 mols of pyridine-3-carboxylic acid.
References Cited in the file of this patent 6l43arltrop: J. Chem. Soc. (London), 1954, pp. 159-
Claims (1)
1. THE SALT OF ISOBEBEERINE AND AN ACID SELECTED FROM THE GROUP CONSISTING OF PYRIDINE-2-CARBOXYLIC ACID AND PYRIDINE-3-CARBOXYLIC ACID.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US780952A US2947741A (en) | 1958-12-17 | 1958-12-17 | Isobebeerine nicotinate |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US780952A US2947741A (en) | 1958-12-17 | 1958-12-17 | Isobebeerine nicotinate |
Publications (1)
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US2947741A true US2947741A (en) | 1960-08-02 |
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US780952A Expired - Lifetime US2947741A (en) | 1958-12-17 | 1958-12-17 | Isobebeerine nicotinate |
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3092634A (en) * | 1959-08-24 | 1963-06-04 | Synergistics Inc | Novel [nitric acid ester] derivatives of nicotinic acid |
US3168438A (en) * | 1962-08-09 | 1965-02-02 | Synergistics Inc | Vasodilation by nitric acid ester derivatives of nicotinic acid |
-
1958
- 1958-12-17 US US780952A patent/US2947741A/en not_active Expired - Lifetime
Non-Patent Citations (1)
Title |
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None * |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3092634A (en) * | 1959-08-24 | 1963-06-04 | Synergistics Inc | Novel [nitric acid ester] derivatives of nicotinic acid |
US3168438A (en) * | 1962-08-09 | 1965-02-02 | Synergistics Inc | Vasodilation by nitric acid ester derivatives of nicotinic acid |
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