JPS632956B2 - - Google Patents
Info
- Publication number
- JPS632956B2 JPS632956B2 JP13076285A JP13076285A JPS632956B2 JP S632956 B2 JPS632956 B2 JP S632956B2 JP 13076285 A JP13076285 A JP 13076285A JP 13076285 A JP13076285 A JP 13076285A JP S632956 B2 JPS632956 B2 JP S632956B2
- Authority
- JP
- Japan
- Prior art keywords
- acid
- addition compound
- nicotinamide
- higher fatty
- acid amide
- 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
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 65
- 235000005152 nicotinamide Nutrition 0.000 claims description 33
- 239000011570 nicotinamide Substances 0.000 claims description 33
- 150000001875 compounds Chemical class 0.000 claims description 30
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 15
- 239000000194 fatty acid Substances 0.000 claims description 15
- 229930195729 fatty acid Natural products 0.000 claims description 15
- 150000004665 fatty acids Chemical class 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 239000003960 organic solvent Substances 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 229960003966 nicotinamide Drugs 0.000 description 15
- 239000013078 crystal Substances 0.000 description 14
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 10
- 235000021355 Stearic acid Nutrition 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 8
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 8
- 235000019658 bitter taste Nutrition 0.000 description 6
- YAQXGBBDJYBXKL-UHFFFAOYSA-N iron(2+);1,10-phenanthroline;dicyanide Chemical compound [Fe+2].N#[C-].N#[C-].C1=CN=C2C3=NC=CC=C3C=CC2=C1.C1=CN=C2C3=NC=CC=C3C=CC2=C1 YAQXGBBDJYBXKL-UHFFFAOYSA-N 0.000 description 6
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 6
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 238000000862 absorption spectrum Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 206010013911 Dysgeusia Diseases 0.000 description 2
- DFPAKSUCGFBDDF-ZQBYOMGUSA-N [14c]-nicotinamide Chemical compound N[14C](=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-ZQBYOMGUSA-N 0.000 description 2
- KEMQGTRYUADPNZ-UHFFFAOYSA-N heptadecanoic acid Chemical compound CCCCCCCCCCCCCCCCC(O)=O KEMQGTRYUADPNZ-UHFFFAOYSA-N 0.000 description 2
- RQFLGKYCYMMRMC-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O.CCCCCCCCCCCCCCCCCC(O)=O RQFLGKYCYMMRMC-UHFFFAOYSA-N 0.000 description 2
- SZHOJFHSIKHZHA-UHFFFAOYSA-N tridecanoic acid Chemical compound CCCCCCCCCCCCC(O)=O SZHOJFHSIKHZHA-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- KYYWBEYKBLQSFW-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O.CCCCCCCCCCCCCCCC(O)=O KYYWBEYKBLQSFW-UHFFFAOYSA-N 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 150000005480 nicotinamides Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000013076 target substance Substances 0.000 description 1
- ZTUXEFFFLOVXQE-UHFFFAOYSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCCC(O)=O.CCCCCCCCCCCCCC(O)=O ZTUXEFFFLOVXQE-UHFFFAOYSA-N 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
Landscapes
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
本発明はニコチン酸アミドと高級脂肪酸との付
加化合物及びその製造法に関する。
ニコチン酸アミドは、人間にとつて欠くことの
できない重要なビタミンの１種であるが、苦味が
ありまた吸湿性もあつて製剤とするうえに多少難
点がある。本発明者らは、このようなニコチン酸
アミドの苦味の少ない、また吸湿性の低い製剤を
得るため、種々研究を行つた結果、ニコチン酸ア
ミドと高級脂肪酸とが一定組成の苦味のほとんど
ない付加化合物を生成することを見出した。
本発明は、ニコチン酸アミドと炭素数12〜18の
高級脂肪酸との等モル付加化合物である。
本発明の付加化合物は、ニコチン酸アミドと炭
素数12〜18の高級脂肪酸とを有機溶剤中で反応さ
せることにより得られる。
ニコチン酸アミドは医薬品として純度の高いも
のが用いられ、日本薬局方規格のものが好まし
い。炭素数12〜18の高級脂肪酸としては、オクタ
デカン酸（ステアリン酸）、ヘプタデカン酸、ヘ
キサデカン酸（パルミチン酸）、ペンタデカン酸、
テトラデカン酸（ミリスチン酸）、トリデカン酸
及びドデカン酸（ラウリン酸）が用いられる。こ
れらの高級脂肪酸は高純度のものが好ましい。オ
クタデカン酸などの日本薬局方収載品では、融点
にやや幅がみられるが、これらを用いることもで
きる。有機溶剤としては、ハロゲン化炭化水素、
特に１，２―ジクロルエタンが好ましい。そのほ
かニコチン酸アミド及び高級脂肪酸の両者に対し
て反応性がなく、また両者を適当に濃度に溶解す
るものであれば使用できる。ただし極性の強いも
のや、極性の極端に弱いものでは付加化合物の生
成がみられないことがある。
本発明の付加化合物を製造するに際しては、ニ
コチン酸アミドと炭素数12〜18の高級脂肪酸を有
機溶剤に溶解する。ニコチン酸アミドと高級脂肪
酸はモル比で１：１程度の割合で用いることが好
ましい。また両者を溶解する場合は60〜90℃に加
温することが好ましい。この溶液を０℃ないし室
温に放置すると、白色の結晶が析出する。これを
取し、溶剤で洗浄したのち乾燥すると、目的物
質が得られる。
本発明の付加化合物は、次式で表わされる。式
中のｎは10ないし16の数である。
本発明の付加化合物は、ニコチン酸アミドに比
べて著しく苦味が減少しているので散剤、顆粒剤
などの剤形でも服用が容易であり、また臨界湿度
がニコチン酸アミドより高く、保存性にも優れて
いる。
実施例 １
ニコチン酸アミド10.0g（0.082モル）とオクタ
デカン酸（ステアリン酸）23.4g（0.082モル）と
を、１，２―ジクロルエタン1000mlに加温溶解し
た。この溶液を30℃で48時間放置したのち、析出
した結晶を取し、少量の１，２―ジクロルエタ
ンで洗浄し、乾燥すると、融点83〜85℃のニコチ
ン酸アミドとオクタデカン酸との付加化合物の白
色長板状結晶30.7g（計算値33.4gに対する収量92
％）が得られた。
この結晶はろう様の感触を呈し、苦味を感じな
い。またこの結晶をエタノールに溶解し、含有さ
れるオクタデカン酸の量を水酸化カリウム・エタ
ノール溶液で滴定定量したところ、ニコチン酸ア
ミドとオクデカン酸の含有比率はモル比で１：
1.02であつた。
実施例 ２
ニコチン酸アミド10.0g（0.082モル）とペンタ
デカン酸20.0g（0.083モル）とを、１，２―ジク
ロルエタン1200mlに加温溶解した。この溶液を室
温で12時間放置したのち、実施例１と同様に処理
すると、融点77〜79℃のニコチン酸アミドとペン
タデカン酸との付加化合物の白色長板状結晶
28.4g（計算値29.9に対する収量95％）が得られ
た。
このニコチン酸アミド・ペンタデカン酸付加化
合物の結晶も、実施例１に示したニコチン酸アミ
ド・オクタデカン酸付加化合物の結晶と同様にろ
う様の感触を呈し、苦味を感じない。またこの結
晶について、ペンタデカン酸を定量した結果、付
加化合物中のニコチン酸アミドとペンタデカン酸
との含有比率はモル比で１：0.99であつた。
実施例 ３
ニコチン酸アミド10.0g（0.082モル）とドデカ
ン酸（ラウリン酸）17.0g（0.084モル）とを、１，
２―ジクロルエタン500mlに加温溶解した。この
溶液を５℃前後の低温で12時間放置したのち、実
施例１と同様に処理すると、融点67〜69℃のニコ
チン酸アミドとドデカン酸との付加化合物の白色
長板状結晶25.4g（計算値26.4gに対する収量96％）
が得られた。
このニコチン酸アミド・ドデカン酸付加化合物
の結晶もろう様の感触を呈し、苦味を感じない。
またこの結晶についてドデカン酸を定量した結
果、付加化合物中のニコチン酸アミドとドデカン
酸との含有比率はモル比で１：1.01であつた。
同様にして得られるニコチン酸アミドと高級脂
肪酸との付加化合物の融点及び各成分の含有比率
を第１表に示す。これらの付加化合物はいずれも
ろう様の感触の白色長板状結晶で苦味を呈しなか
つた。
The present invention relates to an addition compound of nicotinamide and higher fatty acid and a method for producing the same. Nicotinic acid amide is an important vitamin indispensable to humans, but it has a bitter taste and is hygroscopic, making it somewhat difficult to prepare into preparations. The present inventors conducted various studies in order to obtain a formulation of nicotinamide with little bitterness and low hygroscopicity, and found that nicotinamide and higher fatty acids were added with a certain composition with almost no bitterness. It was discovered that the compound was produced. The present invention is an equimolar addition compound of nicotinamide and a higher fatty acid having 12 to 18 carbon atoms. The addition compound of the present invention is obtained by reacting nicotinic acid amide and a higher fatty acid having 12 to 18 carbon atoms in an organic solvent. Nicotinic acid amide with high purity is used as a pharmaceutical, and those that meet Japanese Pharmacopoeia standards are preferred. Higher fatty acids having 12 to 18 carbon atoms include octadecanoic acid (stearic acid), heptadecanoic acid, hexadecanoic acid (palmitic acid), pentadecanoic acid,
Tetradecanoic acid (myristic acid), tridecanoic acid and dodecanoic acid (lauric acid) are used. These higher fatty acids are preferably of high purity. Products listed in the Japanese Pharmacopoeia, such as octadecanoic acid, have slightly different melting points, but these can also be used. Examples of organic solvents include halogenated hydrocarbons,
Particularly preferred is 1,2-dichloroethane. In addition, it can be used as long as it has no reactivity with both nicotinic acid amide and higher fatty acids and dissolves both in an appropriate concentration. However, if the polarity is strong or the polarity is extremely weak, the formation of additional compounds may not be observed. When producing the addition compound of the present invention, nicotinic acid amide and a higher fatty acid having 12 to 18 carbon atoms are dissolved in an organic solvent. It is preferable to use nicotinic acid amide and higher fatty acid in a molar ratio of about 1:1. Moreover, when both are dissolved, it is preferable to heat to 60 to 90°C. When this solution is left at 0°C to room temperature, white crystals precipitate. When this is taken, washed with a solvent, and then dried, the target substance is obtained. The addition compound of the present invention is represented by the following formula. n in the formula is a number from 10 to 16. The addition compound of the present invention has a significantly reduced bitterness compared to nicotinamide, so it is easy to take in dosage forms such as powders and granules, and has a higher critical humidity than nicotinamide, making it easier to store. Are better. Example 1 10.0 g (0.082 mol) of nicotinic acid amide and 23.4 g (0.082 mol) of octadecanoic acid (stearic acid) were dissolved under heating in 1000 ml of 1,2-dichloroethane. After this solution was left at 30°C for 48 hours, the precipitated crystals were collected, washed with a small amount of 1,2-dichloroethane, and dried. 30.7g of white oblong crystals (yield: 92 for calculated value of 33.4g)
%)was gotten. The crystals have a waxy feel and do not taste bitter. Furthermore, when this crystal was dissolved in ethanol and the amount of octadecanoic acid contained was determined by titration with potassium hydroxide/ethanol solution, the content ratio of nicotinic acid amide and octadecanoic acid was found to be 1:1 in molar ratio.
It was 1.02. Example 2 10.0 g (0.082 mol) of nicotinic acid amide and 20.0 g (0.083 mol) of pentadecanoic acid were dissolved under heating in 1,200 ml of 1,2-dichloroethane. After this solution was left to stand at room temperature for 12 hours, it was treated in the same manner as in Example 1 to produce white long plate-shaped crystals of an addition compound of nicotinamide and pentadecanoic acid with a melting point of 77-79°C.
28.4 g (95% yield based on calculated value of 29.9) was obtained. Similar to the crystals of the nicotinamide/octadecanoic acid addition compound shown in Example 1, the crystals of the nicotinamide/pentadecanoic acid addition compound also have a waxy feel and do not taste bitter. Further, as a result of quantifying pentadecanoic acid in this crystal, the molar ratio of nicotinic acid amide and pentadecanoic acid in the addition compound was 1:0.99. Example 3 10.0 g (0.082 mol) of nicotinic acid amide and 17.0 g (0.084 mol) of dodecanoic acid (lauric acid) were mixed into 1,
The mixture was heated and dissolved in 500 ml of 2-dichloroethane. This solution was allowed to stand at a low temperature of around 5°C for 12 hours, and then treated in the same manner as in Example 1. 25.4g of white long plate-shaped crystals of an addition compound of nicotinamide and dodecanoic acid with a melting point of 67-69°C (calculated) Yield 96% for value 26.4g)
was gotten. This nicotinamide/dodecanoic acid addition compound exhibits a crystalline wax-like texture and no bitter taste.
Further, as a result of quantifying dodecanoic acid in this crystal, the molar ratio of nicotinic acid amide and dodecanoic acid in the addition compound was 1:1.01. Table 1 shows the melting point and content ratio of each component of the addition compound of nicotinic acid amide and higher fatty acid obtained in the same manner. All of these adducts were white oblong crystals with a waxy feel and no bitter taste.
【表】
＊ 定量値
各付加化合物の溶融の状況を顕微鏡下に観察す
るといずれも融点で溶融するが、なお加熱を続け
ると溶融した液滴の中にニコチン酸アミドの結晶
が析出し、さらに加熱を続けると析出した結晶は
110℃付近の温度で液滴の中に溶解する。これは
融点で溶融した時点で付加化合物を形成していた
ニコチン酸アミドと高級脂肪酸とがそれぞれに分
離したことを示しているものと思われる。
さらに、これら付加化合物の元素分析の結果を
第２表に示すが、ニコチン酸アミド１モルと高級
脂肪酸１モルとからなる付加化合物として計算し
た計算値によく一致している。[Table] * Quantitative value Observing the melting state of each addition compound under a microscope, all of them melt at their melting point, but if heating continues, nicotinamide crystals precipitate in the molten droplets, and further heating If you continue, the crystals that precipitate will be
It dissolves into droplets at temperatures around 110°C. This seems to indicate that nicotinic acid amide and higher fatty acid, which had formed an addition compound at the time of melting at the melting point, were separated. Furthermore, the results of elemental analysis of these adduct compounds are shown in Table 2, which agree well with the calculated values calculated for an adduct compound consisting of 1 mole of nicotinic acid amide and 1 mole of higher fatty acid.
【表】
また図面にニコチン酸アミド１モルとオクタデ
カン酸１モルとの混合物及び本発明のニコチン酸
アミド・オクタデカン酸付加化合物のKBr錠剤
法によつて測定した赤外吸収スペクトルを示す。
図面の曲線ａは混合物、曲線ｂは付加化合物の吸
収スペクトルである。両者は波数300〜3200cm-1
及び1600〜1800cm-1付近のスペクトルに相違が認
められ、本発明の付加化合物が単なる混合物でな
いことは明らかである。
本発明の付加化合物の吸湿性を調べるため、実
施例１で得られたニコチン酸アミド・オクタデカ
ン酸付加化合物及び対照としてニコチン酸アミド
をとり、これらの試料約2gを精密に秤量し、40
℃で相対湿度70％、80％、90％及び100％の条件
下に放置して10日間にわたり重量の変化を調べ
た。その結果を第３〜６表に示す。
この結果から、本発明の付加化合物は、高湿度
下においても吸湿がみられず、防湿性の点でも優
れていることが知られる。[Table] The figure also shows infrared absorption spectra measured by the KBr tablet method of a mixture of 1 mole of nicotinamide and 1 mole of octadecanoic acid and the nicotinamide/octadecanoic acid addition compound of the present invention.
Curve a in the drawing is the absorption spectrum of the mixture, and curve b is the absorption spectrum of the addition compound. Both wave numbers are 300 to 3200 cm -1
It is clear that the addition compound of the present invention is not a mere mixture. In order to examine the hygroscopicity of the addition compound of the present invention, the nicotinamide/octadecanoic acid addition compound obtained in Example 1 and nicotinamide were taken as a control, and about 2 g of these samples were accurately weighed, and
The samples were left at 70%, 80%, 90% and 100% relative humidity at 100° C. for 10 days to examine changes in weight. The results are shown in Tables 3-6. From this result, it is known that the addition compound of the present invention does not absorb moisture even under high humidity and is excellent in terms of moisture resistance.
【表】【table】
【表】【table】
【表】【table】
図面はニコチン酸アミドとオクタデカン酸の等
モル量混合物及び本発明の付加化合物の赤外吸収
スペクトルを比較して示すものであつて、曲線ａ
は混合物、曲線ｂは付加化合物の場合である。
The drawing shows a comparison of the infrared absorption spectra of a mixture of equimolar amounts of nicotinamide and octadecanoic acid and the addition compound of the present invention, in which curve a
is for the mixture, and curve b is for the addition compound.
Claims (1)
酸との等モル付加化合物。 ２ ニコチン酸アミドと炭素数12〜18の高級脂肪
酸とを有機溶剤中で反応させることを特徴とす
る、ニコチン酸アミドと炭素数12〜18の高級脂肪
酸との等モル付加化合物の製造法。[Scope of Claims] 1. Equimolar addition compound of nicotinic acid amide and higher fatty acid having 12 to 18 carbon atoms. 2. A method for producing an equimolar addition compound of nicotinic acid amide and a higher fatty acid having 12 to 18 carbon atoms, which comprises reacting nicotinic acid amide and a higher fatty acid having 12 to 18 carbon atoms in an organic solvent.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13076285A JPS61289078A (en) | 1985-06-18 | 1985-06-18 | Addition compound of nicotinamide and higher fatty acid and production thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13076285A JPS61289078A (en) | 1985-06-18 | 1985-06-18 | Addition compound of nicotinamide and higher fatty acid and production thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61289078A JPS61289078A (en) | 1986-12-19 |
| JPS632956B2 true JPS632956B2 (en) | 1988-01-21 |
Family
ID=15042047
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP13076285A Granted JPS61289078A (en) | 1985-06-18 | 1985-06-18 | Addition compound of nicotinamide and higher fatty acid and production thereof |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61289078A (en) |
-
1985
- 1985-06-18 JP JP13076285A patent/JPS61289078A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61289078A (en) | 1986-12-19 |
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