JPS60132964A - Thiamine disulfide addition compound and its preparation - Google Patents
Thiamine disulfide addition compound and its preparationInfo
- Publication number
- JPS60132964A JPS60132964A JP24087583A JP24087583A JPS60132964A JP S60132964 A JPS60132964 A JP S60132964A JP 24087583 A JP24087583 A JP 24087583A JP 24087583 A JP24087583 A JP 24087583A JP S60132964 A JPS60132964 A JP S60132964A
- Authority
- JP
- Japan
- Prior art keywords
- thiamine disulfide
- addition compound
- thiamine
- higher fatty
- disulfide
- 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.)
- Granted
Links
- GFEGEDUIIYDMOX-BMJUYKDLSA-N n-[(4-amino-2-methylpyrimidin-5-yl)methyl]-n-[(z)-3-[[(z)-2-[(4-amino-2-methylpyrimidin-5-yl)methyl-formylamino]-5-hydroxypent-2-en-3-yl]disulfanyl]-5-hydroxypent-2-en-2-yl]formamide Chemical compound C=1N=C(C)N=C(N)C=1CN(C=O)C(\C)=C(CCO)/SSC(/CCO)=C(/C)N(C=O)CC1=CN=C(C)N=C1N GFEGEDUIIYDMOX-BMJUYKDLSA-N 0.000 title claims abstract description 33
- 229960001385 thiamine disulfide Drugs 0.000 title claims abstract description 33
- 150000001875 compounds Chemical class 0.000 title claims abstract description 27
- 238000002360 preparation method Methods 0.000 title abstract description 5
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 17
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 16
- 239000000194 fatty acid Substances 0.000 claims abstract description 16
- 229930195729 fatty acid Natural products 0.000 claims abstract description 16
- 239000002904 solvent Substances 0.000 claims abstract description 6
- 238000004519 manufacturing process Methods 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 229960003495 thiamine Drugs 0.000 abstract description 12
- KYMBYSLLVAOCFI-UHFFFAOYSA-N thiamine Chemical compound CC1=C(CCO)SCN1CC1=CN=C(C)N=C1N KYMBYSLLVAOCFI-UHFFFAOYSA-N 0.000 abstract description 12
- JZRWCGZRTZMZEH-UHFFFAOYSA-N Thiamine Natural products CC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N JZRWCGZRTZMZEH-UHFFFAOYSA-N 0.000 abstract description 11
- 235000019157 thiamine Nutrition 0.000 abstract description 11
- 239000011721 thiamine Substances 0.000 abstract description 11
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 abstract description 6
- 235000019658 bitter taste Nutrition 0.000 abstract description 6
- 239000008187 granular material Substances 0.000 abstract description 5
- 239000002552 dosage form Substances 0.000 abstract description 4
- 239000000843 powder Substances 0.000 abstract description 3
- 238000003860 storage Methods 0.000 abstract description 2
- 229930003451 Vitamin B1 Natural products 0.000 abstract 1
- 239000004503 fine granule Substances 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 239000011691 vitamin B1 Substances 0.000 abstract 1
- 235000010374 vitamin B1 Nutrition 0.000 abstract 1
- 239000013078 crystal Substances 0.000 description 11
- 238000002844 melting Methods 0.000 description 11
- 230000008018 melting Effects 0.000 description 10
- 235000021355 Stearic acid Nutrition 0.000 description 6
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 6
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 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 3
- 238000000034 method Methods 0.000 description 3
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- RZJRJXONCZWCBN-UHFFFAOYSA-N octadecane Chemical compound CCCCCCCCCCCCCCCCCC RZJRJXONCZWCBN-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
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- 150000003544 thiamines Chemical class 0.000 description 2
- GTQXMAIXVFLYKF-UHFFFAOYSA-N thiochrome Chemical compound CC1=NC=C2CN3C(C)=C(CCO)SC3=NC2=N1 GTQXMAIXVFLYKF-UHFFFAOYSA-N 0.000 description 2
- QIJRTFXNRTXDIP-UHFFFAOYSA-N (1-carboxy-2-sulfanylethyl)azanium;chloride;hydrate Chemical compound O.Cl.SCC(N)C(O)=O QIJRTFXNRTXDIP-UHFFFAOYSA-N 0.000 description 1
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
- 206010013911 Dysgeusia Diseases 0.000 description 1
- 229930003270 Vitamin B Natural products 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229960001305 cysteine hydrochloride Drugs 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000007941 film coated tablet Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 229940038384 octadecane Drugs 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- YLLIGHVCTUPGEH-UHFFFAOYSA-M potassium;ethanol;hydroxide Chemical compound [OH-].[K+].CCO YLLIGHVCTUPGEH-UHFFFAOYSA-M 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000007940 sugar coated tablet Substances 0.000 description 1
- 239000013076 target substance Substances 0.000 description 1
- 235000019640 taste Nutrition 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- 235000019156 vitamin B Nutrition 0.000 description 1
- 239000011720 vitamin B Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
【発明の詳細な説明】
本発明はチアミンジスルフィドと高級脂肪酸からの新規
な付加化合物及びその製造法に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a novel addition compound from thiamine disulfide and higher fatty acids and a method for producing the same.
チアミンジスルフィドはチアミン誘導体の１つとして、
その効力が評価されているものであり、一般にチアミン
塩類ｒ比べて安定性に優れ、広くビタミンＢ、含有製剤
の製造に使用されている。しかしチアミンジスルフィド
は苦味が強く、錠剤特に糖衣錠、フィルムコーティング
錠、カプセル剤などの剤形で投与する場合には問題ない
が、散剤又はチュアブルな剤形、日中で溶解するような
崩壊性の優れた顆粒剤、細粒剤などの剤形で投与するこ
とは困難である。Thiamine disulfide is one of the thiamine derivatives.
Its efficacy has been evaluated, and it is generally more stable than thiamine salts, and is widely used in the production of vitamin B-containing preparations. However, thiamine disulfide has a strong bitter taste, and while it poses no problem when administered in the form of tablets, especially sugar-coated tablets, film-coated tablets, and capsules, it is difficult to administer in powder or chewable dosage forms or with excellent disintegration that dissolves during the day. It is difficult to administer in dosage forms such as granules and fine granules.
本発明者らは、このよ５なチアミンジスルフィドの苦味
の少ない製剤を得るため、研究を行った結果、チアミン
ジスルフィ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。The present inventors conducted research in order to obtain a less bitter preparation of thiamine disulfide, and as a result, they discovered that thiamine disulfide and higher fatty acids form an addition compound with a certain composition that has almost no bitterness. .
本発明は、チアミンジスルフィドと炭素数１２〜１８の
高級脂肪酸とのモル比が１：６であるチアミンジスルフ
ィドと高級脂肪酸の伺加化合物である。The present invention is an additive compound of thiamine disulfide and higher fatty acid in which the molar ratio of thiamine disulfide to higher fatty acid having 12 to 18 carbon atoms is 1:6.
本発明に用いられる炭素数１２〜１８の高級脂肪酸とし
ては例えばオクタデカン酸（ステアリン酸）、ペンタデ
カン酸、ドデカン酸（ラウリン酸）などがあげられる。Examples of higher fatty acids having 12 to 18 carbon atoms used in the present invention include octadecanoic acid (stearic acid), pentadecanoic acid, and dodecanoic acid (lauric acid).
高級脂肪酸は高純度のものが好ましいが、オクタデカン
酸等の日本薬局方収載品では、日本薬局方の純度のもの
であれば、融点にやや幅がみられても用いることができ
る。High purity fatty acids are preferred, but products listed in the Japanese Pharmacopoeia, such as octadecanoic acid, can be used even if their melting points vary slightly, as long as they meet the purity requirements of the Japanese Pharmacopoeia.
チアミンジスルフィドとしては、医薬品としての規格に
適合するものを用いることが好ましい。市販のチアミン
ジスルフィドは融点１２０〜１４０℃の低融点型と呼ば
れるもので、吸湿性が強く、通常５〜６％の水分を含む
ものが多いが、これをそのまま用いることができる。ま
た融点１７０℃以上の高融点型を用いても、付加化合物
を得ることができる。As the thiamine disulfide, it is preferable to use one that meets the standards as a pharmaceutical product. Commercially available thiamine disulfide is a so-called low-melting type with a melting point of 120 to 140°C, and has strong hygroscopicity and usually contains 5 to 6% water, but it can be used as is. Further, the addition compound can also be obtained by using a high melting point type having a melting point of 170° C. or higher.
本発明の付加化合物の製造は、チアミン、ジスルフィド
と炭素数１２〜１８の高級脂肪酸とを□溶媒中で反応さ
せることにより行われる。高級脂肪酸の使用量は、チア
ミンジスルフィド１モルに対し６モル程度が好ましい。The addition compound of the present invention is produced by reacting thiamine, disulfide, and a higher fatty acid having 12 to 18 carbon atoms in a solvent. The amount of higher fatty acid used is preferably about 6 mol per 1 mol of thiamine disulfide.
溶媒としてはチアミンジスルフィド及び高級脂肪酸が溶
解するものであればよく、例えば１，２〜ジクロルエタ
ン、クロロホルムなどが用いられる。溶解温度は６０〜
９０’Ｃ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ｒ取し、溶媒で
洗浄したのち乾燥すると、目的物質が得られる。The solvent may be any solvent that can dissolve thiamine disulfide and higher fatty acids, such as 1,2-dichloroethane, chloroform, and the like. Melting temperature is 60~
90'C is preferred. When this solution is left at 0°C to room temperature, white crystals precipitate. When this is collected, washed with a solvent, and then dried, the target substance is obtained.
本発明の付加化合物は、次式で表わされる。The addition compound of the present invention is represented by the following formula.
式中のｎは１０ないし１６の数である。n in the formula is a number from 10 to 16.
本発明、の付加化合物は、チアミンジスルフィドに比べ
て著しく苦・味が減少しているの・で、散剤、顆粒剤、
細粒剤などの剤形でも容易に内服することができる。ま
た高湿度下の保存では、チアミンジスルフィドより臨界
湿度が高く、保存性にも優れている。The addition compound of the present invention has significantly reduced bitterness and taste compared to thiamine disulfide, so it can be used in powders, granules, etc.
It can also be easily taken internally in dosage forms such as fine granules. Furthermore, when stored under high humidity, the critical humidity is higher than that of thiamine disulfide, and it has excellent storage stability.
実施例１
チアミンジスルフィド１１．３．９（０，０２モル）及
びオクタデカン酸（ステアリン酸）６４．２９１（０，
１２モル）を１，２−ジクロルエタン１２００ｍｅに加
温溶解した。この溶液を６０℃で４８時間放置したのち
、析出した結晶をＦ取し、少量の１，２−ジクロルエタ
ンで洗浄したのち乾燥すると、融点８０〜８１℃のチア
ミンジスルフィド−オクタデカン酸付加化合物の白色結
晶４２、３ｇ（計算値４５．５ ｇに対する収量９３％
）が得られた。Example 1 Thiamine disulfide 11.3.9 (0.02 mol) and octadecanoic acid (stearic acid) 64.291 (0.02 mol)
12 mol) was dissolved under heating in 1200 me of 1,2-dichloroethane. After this solution was left to stand at 60°C for 48 hours, the precipitated crystals were collected, washed with a small amount of 1,2-dichloroethane, and dried to produce white crystals of a thiamine disulfide-octadecanoic acid addition compound with a melting point of 80-81°C. 42.3g (yield 93% for calculated value 45.5g)
)was gotten.
・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
カン物の量を水酸化カリウム−エタノール液で定量し、
一方、この結晶からチアミンジスルフィドを塩酸試液で
抽出し、塩酸システィンで処理したのちチオクロム法で
定量したところ、チアミンジスルフィドとオクタデカン
酸の含量比率はモル比で１：６．０４であった。・This crystal has a waxy feel and no bitter taste. In addition, the crystals were dissolved in ethanol, and the amount of octadecane contained was determined using a potassium hydroxide-ethanol solution.
On the other hand, when thiamine disulfide was extracted from the crystals with a hydrochloric acid test solution, treated with cysteine hydrochloride, and then quantified by the thiochrome method, the molar ratio of thiamine disulfide to octadecanoic acid was 1:6.04.
本発明のチアミンジスルフィド−オクタデカン酸付加化
合物（１））及びチアミンジスルフィド１モルとオクタ
デカン酸６モルの混合物（ａ）の赤外吸収スペクトル（
臭化カリウム錠剤法）を図面に示す。両者は波数６−２
００ ｃＴｎ−’及び１６００〜１８０ Ｑ ｃｍ−’
付近に相違がみられ、本発明の付加化合物が単な地温合
物でないことが知られる。Infrared absorption spectra of the thiamine disulfide-octadecanoic acid addition compound (1)) of the present invention and the mixture (a) of 1 mole of thiamine disulfide and 6 moles of octadecanoic acid (
Potassium bromide tablet method) is shown in the drawing. Both wave numbers are 6-2
00 cTn-' and 1600-180 Q cm-'
Differences can be seen in the vicinity, indicating that the addition compound of the present invention is not a mere geothermal compound.
実施例２
チア遼ンシスルフイド２．８ｇ ＜ ｏ、ｏ ｏ、ｓモ
ル）及びペンタデカン酸７．３ ｙ （ｏ、 ０３モル
）を１．２−ジクロルエタン４５ｍＩ！に加温溶解した
。この溶液を室温で１２時間放置しへのち、実施例１と
同様に処理すると、融点６７〜６９°Ｃのチアミンジス
ルフィド−ペンタデカン酸伺加化合物の白色結晶９．８
ｇ（ｊｌ算値１０１ｇに対する収量９７％）が得られ
た。Example 2 2.8 g of thialiaon cisulfide (< o, o, s mol) and 7.3 y (o, 03 mol) of pentadecanoic acid were mixed with 45 mI of 1,2-dichloroethane! Dissolved by heating. This solution was allowed to stand at room temperature for 12 hours and then treated in the same manner as in Example 1, resulting in white crystals of thiamine disulfide-pentadecanoic acid compound having a melting point of 67-69°C.
g (yield 97% based on jl calculated value of 101 g) was obtained.
このチアミンジスルフィド−ペンタデカン酸付加化合物
の結晶も、実施例１に示したチアミンジスルフィド−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。またチアミンジスルフィド及び
ペンタデカン酸をそれぞれ定量した結果から得られた両
者の全量比率はモル比で１：６．０５であった。Similar to the crystals of the thiamine disulfide-octadecanoic acid addition compound shown in Example 1, the crystals of the thiamine disulfide-pentadecanoic acid addition compound also have a waxy feel and do not taste bitter. Further, the total ratio of thiamine disulfide and pentadecanoic acid obtained from the results of quantitative determination of both was 1:6.05 in terms of molar ratio.
実施例３
チアミンジスルフィド１６．９Ｍ？（０，０３モル）及
びドデカン酸（ラウリン酸） ３６．１．９ （０，１
８モル）を１，２−ジクロルエタン６ｏｏｍｅＶｃ加温
溶解し、この溶液を０〜５°Ｃ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５３〜５５
℃のチアミンジスルフィド−ドデカン酸付加物の白色結
晶５２．０９ （計算値５６０ｇに対する収量９８％）
が得られた。Example 3 Thiamine disulfide 16.9M? (0,03 mol) and dodecanoic acid (lauric acid) 36.1.9 (0,1
8 mol) of 1,2-dichloroethane was dissolved by heating at 6 oomeVc, and this solution was left at a low temperature of 0 to 5°C for 12 hours, and then treated in the same manner as in Example 1, resulting in a melting point of 53 to 55
℃ white crystals of thiamine disulfide-dodecanoic acid adduct 52.09 (yield 98% based on calculated value 560 g)
was gotten.
この結晶も、ろう様の感触を呈し、苦味を感じない。ま
たチアミンジスルフィド及びドデカン酸をそれぞれ定量
した結果から得られた両者の含量比率はモル比で１：５
．９３であった。This crystal also has a waxy feel and no bitter taste. In addition, the content ratio of both thiamine disulfide and dodecanoic acid obtained from the results of quantitative determination was 1:5 in molar ratio.
．． It was 93.
同様にして得られられチアミンジスルフィド−高級脂肪
酸（１：６）付加化合物の融点を第１表に示す。また伺
加化合物の元素分析値を第２表に示す。Table 1 shows the melting point of the thiamine disulfide-higher fatty acid (1:6) adduct compound obtained in the same manner. Table 2 also shows the elemental analysis values of the compounds.
第 １ 表
第 ２ 表
本発明の伺加化合物の吸湿性を調べるため、チアミンジ
スルフィド−オクタデカン酸伺加化合物（試料１）、チ
アミンジスルフィド−ヘキサデカン酸付加化合物（試料
２）及び対照として市販のチアミンジスルフィド〔融点
１６５〜１６６℃（発泡分解）、水分５．６％〕を用い
、この６種の試料を約２９ずつ精密に秤量し、４０℃で
相対湿度７０％、８ｏ％及び９０％の条件下に解放のま
ま放置して１０日間にわたり重量の変化を調べた。その
結果を第６〜５表に示す。Table 1 Table 2 To investigate the hygroscopic properties of the additive compounds of the present invention, thiamine disulfide-octadecanoic acid additive compound (Sample 1), thiamine disulfide-hexadecanoic acid adduct compound (Sample 2), and commercially available thiamine disulfide as a control were used. Using [melting point 165-166°C (foaming decomposition), moisture 5.6%], these six types of samples were accurately weighed in groups of 29, and were incubated at 40°C and relative humidity of 70%, 8o%, and 90%. It was left open for 10 days and changes in weight were examined. The results are shown in Tables 6-5.
この結果から本発明の付加化合物は、がなりの高湿度に
おいても吸湿がみられず、防湿性が優れていることが知
られる。From this result, it is known that the addition compound of the present invention does not absorb moisture even at extremely high humidity and has excellent moisture resistance.
第 ６ 表 第 ４ 表 第 ５ 表Table 6 Table 4 Table 5
図面は本発明の伺加化合物と対応する混合物の赤外吸収
スペクトルを比較して示すものであって、曲線ａはチア
ミンジスルフィド１モルとオクタデカン酸６モルの混合
物、曲線すはチアミンジスルフィド−オクタデカン酸付
加化合物の場合である。
出願人 河合製薬株式会社
代理人 弁理士小 林 正 雄
手続補正書（方式）
昭和５９年１月３０日
特許庁長官若 杉 和 夫殿
１事件の表示
３、ＷｎＴＥヶｔ６−びその製法
事件との関係 特許出願人
住 所
（名 称）
４、代 理 人
５、補正命令の日イ；ｊ
６ 補男により増加する発明の数
別紙のとおり正式な図面１通を提出します。
手続補正書（自発
昭和６０年１月？ 日
特許庁長官志 賀 学殿
１、事件の表示
特願昭５８−２４０８７５号
２、Ｊｌ［１７）＄６．アオｙ ２２ ＃ フイ１．。
。イ、。
事件との関係特許出願人
４、代 理 人
５、補正命令の日付
物」を「オクタデカン酸」に改める。The drawing shows a comparison of the infrared absorption spectra of the compound of the present invention and the corresponding mixture, where curve a is a mixture of 1 mole of thiamine disulfide and 6 moles of octadecanoic acid, and curve a is a mixture of thiamine disulfide and octadecanoic acid. This is the case for addition compounds. Applicant Kawai Pharmaceutical Co., Ltd. Agent Patent Attorney Tadashi Kobayashi Procedural Amendment (Method) January 30, 1981 President of the Japan Patent Office Mr. Kazuo Wakasugi 1 Case Indication 3, WnTE Cat 6-Bison Manufacturing Process Case Related Patent applicant address (name) 4. Agent 5. Date of amendment order; j 6. Number of inventions increased by assistant son Submit one official drawing as shown in the attached sheet. Procedural Amendment (Spontaneous January 1985? Japan Patent Office Commissioner Shiga Manabu 1, Indication of Case Patent Application No. 1982-240875 2, Jl [17) $6. Ao y 22 # Hui 1. . . stomach,. Patent applicant 4 related to the case, agent 5, the date of the amendment order" was changed to "octadecanoic acid."
Claims (1)
脂肪酸とのモル比が１＝６であるチアミンジスルフィド
と高級脂肪酸の付加化合物。 ２、 チアミンジスルフィドと炭素数１２〜１８の高級
脂肪酸とを溶媒中で反応させることを特徴とする、チア
ミンジスルフィドと前記高級脂肪酸とのモル比が１：６
であるチアミンジスルフィドと高級脂肪酸の付加化合物
の製法。[Scope of Claims] 1. An addition compound of thiamine disulfide and higher fatty acid in which the molar ratio of thiamine disulfide to higher fatty acid having 12 to 18 carbon atoms is 1=6. 2. Thiamine disulfide and a higher fatty acid having 12 to 18 carbon atoms are reacted in a solvent, and the molar ratio of thiamine disulfide and the higher fatty acid is 1:6.
A method for producing an addition compound of thiamine disulfide and higher fatty acid.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP24087583A JPS60132964A (en) | 1983-12-22 | 1983-12-22 | Thiamine disulfide addition compound and its preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP24087583A JPS60132964A (en) | 1983-12-22 | 1983-12-22 | Thiamine disulfide addition compound and its preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60132964A true JPS60132964A (en) | 1985-07-16 |
| JPS627190B2 JPS627190B2 (en) | 1987-02-16 |
Family
ID=17065991
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP24087583A Granted JPS60132964A (en) | 1983-12-22 | 1983-12-22 | Thiamine disulfide addition compound and its preparation |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60132964A (en) |
-
1983
- 1983-12-22 JP JP24087583A patent/JPS60132964A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS627190B2 (en) | 1987-02-16 |
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