JPH064671B2 - Sialic acid derivative and method for producing the same - Google Patents

Sialic acid derivative and method for producing the same

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Publication number
JPH064671B2
JPH064671B2 JP6974185A JP6974185A JPH064671B2 JP H064671 B2 JPH064671 B2 JP H064671B2 JP 6974185 A JP6974185 A JP 6974185A JP 6974185 A JP6974185 A JP 6974185A JP H064671 B2 JPH064671 B2 JP H064671B2
Authority
JP
Japan
Prior art keywords
sialic acid
formula
compound
acid derivative
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
Application number
JP6974185A
Other languages
Japanese (ja)
Other versions
JPS61243096A (en
Inventor
治夫 小倉
公夫 古畑
秀司 藤田
正善 伊藤
昌治 吉村
善保 志鳥
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
KANTO ISHI PHARMA CO Ltd
Original Assignee
KANTO ISHI PHARMA CO Ltd
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Filing date
Publication date
Application filed by KANTO ISHI PHARMA CO Ltd filed Critical KANTO ISHI PHARMA CO Ltd
Priority to JP6974185A priority Critical patent/JPH064671B2/en
Publication of JPS61243096A publication Critical patent/JPS61243096A/en
Publication of JPH064671B2 publication Critical patent/JPH064671B2/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Description

【発明の詳細な説明】 本発明は免疫学的に活性な、シアル酸誘導体及びその製
造方法に関する。シアル酸は、動物界あるいはいくつか
の細菌の細胞表面にシアロ複合体(糖蛋白、糖脂質、オ
リゴ糖、および多糖)として存在することが知られてい
る。
DETAILED DESCRIPTION OF THE INVENTION The present invention relates to an immunologically active sialic acid derivative and a method for producing the same. Sialic acid is known to exist as a sialo complex (glycoprotein, glycolipid, oligosaccharide, and polysaccharide) on the cell surface of the animal kingdom or some bacteria.

この化合物は近年、神経機能、癌、炎症、免疫、ウィル
ス感染、分化、ホルモンレセプターなど、医学ならびに
薬学的に重要視され、細胞表面に局在する特異な活性分
子として注目されつつある。しかしながらシアロ複合体
においてシアル酸の演ずる役割については、いまだ推測
の域を出るものではない。
In recent years, this compound has been medically and pharmaceutically important, such as nerve function, cancer, inflammation, immunity, virus infection, differentiation, hormone receptor, and the like, and is attracting attention as a specific active molecule localized on the cell surface. However, the role of sialic acid in the sialo complex is still speculative.

この化合物は更に、多くの天然物有機化学者によって研
究され、既に単純な各種誘導体に導かれている。しかし
ながら顕著な生理活性誘導体はまだ知られていない。そ
れ故本発明は、優れた生理活性を有する新規化合物を得
ることにある。
This compound has also been studied by many natural product organic chemists and has already led to various simple derivatives. However, a remarkable bioactive derivative is not yet known. Therefore, the present invention is to obtain a novel compound having excellent physiological activity.

さらに近年、造血臓器の悪性腫瘍をはじめ、各種癌疾
患、膠原病などの治療の多角化によって、確かに延命効
果がもたらされている。しかしその反面、使用する薬剤
例えば副腎皮質ホルモン剤や、免疫抑制剤の使用の頻度
の増加をすることがさけられず、その結果いわゆる免疫
力の低下・減少と共に、多くの副作用がおこりつつあ
る。本発明者等は、生体固有成分であるシアル酸に注目
し、その化学的修飾によって副作用が少なく、かつ免疫
監視機構の調整作用をもつ、免疫調整剤の研究を鋭意行
ない、その結果抑制T細胞を活性化し、B細胞の免疫グ
ロブリン産生を抑制するいわゆる免疫調整作用を持つ本
発明の新規化合物に到達したのである。
Furthermore, in recent years, diversification of treatments for various cancer diseases, collagen diseases, etc., including malignant tumors of hematopoietic organs, has certainly brought about a life prolonging effect. On the other hand, however, it is unavoidable to increase the frequency of use of drugs used, such as corticosteroids and immunosuppressants, and as a result, so-called immunity is reduced / decreased and many side effects are occurring. The present inventors have focused their attention on sialic acid, which is an indigenous component of living organisms, and have conducted diligent research on an immunomodulator that has few side effects due to its chemical modification and that has a regulating action on the immune surveillance mechanism. Thus, a novel compound of the present invention having a so-called immunomodulatory effect of activating erythrocytes and suppressing B cell immunoglobulin production has been reached.

すなわち、本発明は 一般式 (式中、R1及びR2はいずれか一方がカルボキシル基ま
たはメトキシカルボニル基であり、他方が式 で示される基であり、R3は水素またはアセチル基であ
る) で表わされるシアル酸誘導体に関する。
That is, the present invention has the general formula (In the formula, one of R 1 and R 2 is a carboxyl group or a methoxycarbonyl group, and the other is a formula And R 3 is hydrogen or an acetyl group).

また、本発明は 一般式 で示される化合物をコレステロールと反応せしめ、つい
で必要により加水分解することを特徴とする、上記式
〔I〕のシアル酸誘導体の製造方法に関する。
Further, the present invention has the general formula The present invention relates to a method for producing a sialic acid derivative represented by the above formula [I], which comprises reacting a compound represented by the formula (1) with cholesterol and then hydrolyzing the compound if necessary.

前記一般式〔I〕のシアル酸誘導体は、次の化学式で示
すように製造される。
The sialic acid derivative of the general formula [I] is produced as shown by the following chemical formula.

本発明に於いて使用する式〔II〕の化合物は公知化合物
であり、容易に商業的に入手し得る。
The compound of the formula [II] used in the present invention is a known compound and can be easily obtained commercially.

上記製造方法に於いて、式〔II〕の化合物をKoenigs-Kn
orr反応用触媒の存在下にコレステロール常圧で約20
〜25℃の温度で約2〜7日反応させる。その際、コレ
ステロール化合物〔II〕1モルに対して約2〜5倍モル
用いる。
In the above production method, the compound of formula [II] is added to Koenigs-Kn
Approximately 20 cholesterol at normal pressure in the presence of catalyst for orr reaction
The reaction is carried out at a temperature of -25 ° C for about 2-7 days. At that time, it is used in an amount of about 2 to 5 times the mole of the cholesterol compound [II].

尚、上記触媒としては、臭化第二水銀、シアン化第二水
銀、過塩素酸銀、トリフルオロメタンスルホン酸銀、ト
リフルオロ酢酸銀糖が使用できる。
As the catalyst, mercuric bromide, mercuric cyanide, silver perchlorate, silver trifluoromethanesulfonate, and silver trifluoroacetate sugar can be used.

上記触媒は化合物〔II〕1当量に対して約1.0当量〜1.2
当量の範囲で使用する。
The above catalyst is about 1.0 equivalent to 1.2 equivalent to 1 equivalent of the compound [II].
Use within the equivalent range.

また、溶媒としてはアセトニトリル、ニトロメタン、ア
セトン、ベンゼン、テトラヒドロフラン、ジクロルメタ
ン、塩化メチレン等が挙げられる。就中、ベンゼン、テ
トラヒドロフラン、ジクロルメタンが好ましい溶媒であ
る。
Examples of the solvent include acetonitrile, nitromethane, acetone, benzene, tetrahydrofuran, dichloromethane, methylene chloride and the like. Above all, benzene, tetrahydrofuran and dichloromethane are preferred solvents.

かくして得られた反応生成物は、カラムクロマトグラフ
ィーの如き常法により単離、精製される。
The reaction product thus obtained is isolated and purified by a conventional method such as column chromatography.

更に、上記生成物は必要により加水分解してメトキシカ
ルボニル基をカルボキシル基に、アセチル基を水素に変
換し得る。加水分解は、常法により、例えば約1〜3N
のアルカリ溶液で約15〜25℃の温度で約5〜15時
間処理することにより行ない得る。
Further, the above product can be hydrolyzed if necessary to convert a methoxycarbonyl group into a carboxyl group and an acetyl group into hydrogen. Hydrolysis can be carried out by a conventional method, for example, about 1 to 3N.
Can be carried out at a temperature of about 15 to 25 ° C. for about 5 to 15 hours.

本発明に於て、一般式〔I〕で示される化合物は、夫々
顕著な免疫調整作用を有する。
In the present invention, the compounds represented by the general formula [I] each have a remarkable immunomodulating action.

諸免疫調整作用は、次のような方法により確認すること
ができた。
The immunomodulatory effects could be confirmed by the following methods.

ConAによるマウス脾臓リンパ球活性化に対する作用: T細胞は、ConAにより非特異的に活性化されるが、この
反応系に本発明のシアル酸誘導体を加え、その作用を検
討した。即ち、BALB/Cマウスより得た脾臓リンパ球(S
PC)にConA及び一般式〔I〕の化合物を夫々加え、ミ
クロプレート上で37℃で5%CO2を与えながら20
数時間培養した。これにトリチウムで標識したチミジン
を加え、さらに37℃で10数時間培養後、SPCを収
集し、シンチレーションカウンターでSPCに取り込ま
れた3H−チミジンの量を測定した。
Effect of ConA on activation of mouse spleen lymphocytes: T cells are non-specifically activated by ConA. The effect was examined by adding the sialic acid derivative of the present invention to this reaction system. That is, splenic lymphocytes obtained from BALB / C mice (S
To PC), ConA and the compound of the general formula [I] are added respectively, and 20% is given on a microplate at 37 ° C. while giving 5% CO 2.
Cultured for several hours. To this, thymidine labeled with tritium was added, and after further culturing at 37 ° C. for 10 hours, SPC was collected and the amount of 3 H-thymidine incorporated into SPC was measured by a scintillation counter.

一般式〔I〕で示される化合物に関し、3H−チミジン
の取り込み促進・増強が認められ、ConAによるT細胞活
性化に対する増強作用があった。
With respect to the compound represented by the general formula [I], promotion / enhancement of 3 H-thymidine uptake was observed, and there was an enhancing effect on T cell activation by ConA.

マウス脾臓リンパ球の免疫グロブリン産生に対する作
用: 前述の実験により、T細胞活性化作用があらわれた本発
明のシアル酸誘導体について、さらに免疫グロブリン産
生に対する作用をプラーク形成細胞数を測定することに
より検討した。まづSPCに羊赤血球(SRBC)及び
夫々の一般式〔I〕の化合物を加え、37℃で5日培養
した。得られた感作SPCに、再びSRBCおよび補体
を加えた。カニンガム・チャンバー中で37℃3〜12
時間培養後PFC(プラーク形成細胞)を数えた。
Effect of mouse spleen lymphocytes on immunoglobulin production: The sialic acid derivative of the present invention, which showed T cell activating effect in the above-mentioned experiment, was further examined for its effect on immunoglobulin production by measuring the number of plaque-forming cells. . First, sheep red blood cells (SRBC) and each compound of the general formula [I] were added to SPC and cultured at 37 ° C. for 5 days. SRBC and complement were added again to the resulting sensitized SPC. 37 ° C 3-12 in Cunningham chamber
PFCs (plaque forming cells) were counted after the time of culture.

PFCの減少が認められ、かつ細胞生存度は対照標準と
同等であったことから免疫グロブリン産生に対する抑制
作用の増強を確認した。
Since a decrease in PFC was observed and the cell viability was similar to that of the control standard, it was confirmed that the inhibitory effect on immunoglobulin production was enhanced.

本発明の化合物は、前述の二種の試験に於て活性を示し
た。すなわち抑制T細胞の活性化により免疫グロブリン
産生を抑制したものと考えられる。
The compounds of the invention showed activity in the above two tests. That is, it is considered that immunoglobulin production was suppressed by activation of suppressor T cells.

従来、例えば膠原病などの自己免疫疾患においては、抑
制T細胞の機能低下が認められている。それ故、抑制T
細胞活性化作用を有する本発明のシアル酸誘導体は免疫
調整剤として、臨床的応用の有用性が期待される。
Conventionally, in autoimmune diseases such as collagen disease, functional depression of suppressor T cells has been recognized. Therefore, the suppression T
The sialic acid derivative of the present invention having a cell activating effect is expected to be useful in clinical applications as an immunomodulator.

以下、本発明を実施例により説明する。これらの実施例
は、単に本発明を説明するためのものであり、従って勿
論本発明を限定するためのものではない。
Hereinafter, the present invention will be described with reference to examples. These examples are merely illustrative of the invention and are, of course, not intended to limit the invention.

実施例1 メチル5−アセトアミド−4,7,8,9−テトラ−O
−アセチル−2−O−(5−コレステン−3−β−イ
ル)−3,5−ジデオキシ−α−D−グリセロ−D−ガ
ラクト−2−ノニュロピラノソネートの合成 コレステロール3.87g(10mmole)をドライベンゼン20m
に溶解し、これにAgClO40.829g(4mmole)を加え
更にドライライト2gを加えて、室温で1.5時間攪拌し
た。次に式〔II〕の化合物の塩化メチレン50m溶液
を加え、室温で7日間反応させた。
Example 1 Methyl 5-acetamido-4,7,8,9-tetra-O
-Acetyl-2-O- (5-cholesten-3-β-yl) -3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosonate synthesis Cholesterol 3.87 g (10 mmole) 20m of dry benzene
0.829 g ( 4 mmole) of AgClO 4 was added thereto, 2 g of drylite was further added, and the mixture was stirred at room temperature for 1.5 hours. Then, a 50 m solution of the compound of the formula [II] in methylene chloride was added, and the mixture was reacted at room temperature for 7 days.

反応液をセライトロ過し、瀘液を減圧乾固した。残渣を
酢酸エチルに溶解し、飽和食塩水で十分洗浄し、Na2
SO4で乾燥後、酢酸エチルを減圧留去した。褐色粉末
4.78gを得た。
The reaction solution was filtered through Celite, and the filtrate was dried under reduced pressure. The residue was dissolved in ethyl acetate, washed thoroughly with saturated brine, and washed with Na 2
After drying with SO 4 , ethyl acetate was distilled off under reduced pressure. Brown powder
4.78 g was obtained.

このものをカラムクロマトグラフィー(シリカゲル)に
より分離精製し、標題の化合物α体244mg(16.0%)および
β体253mg(16.6%)を得た。
This was separated and purified by column chromatography (silica gel) to give the title compound α-form 244 mg (16.0%) and β-form 253 mg (16.6%).

またメチル5−アセトアミド−4,7,8,9−テトラ
−O−アセチル−2,6−アンハイドロ−3,5−ジデ
オキシ−D−グリセロ−D−ガラクト−ノン−2−エン
−オネイト106mg(11.2%)を得た。
Also, methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2,6-anhydro-3,5-dideoxy-D-glycero-D-galacto-non-2-ene-oneate 106 mg ( 11.2%).

標題化合物の物理恒数 Mass(EI)m/z859(M+),800(M+-59) 1H NMR CDCl3 δ(TMS) 90MHz 0.68 3H,s,CH3-18 0.84と0.87 6H,CH3-26,CH3=27 0.90 3H.d,J=4.5Hz,CH3-21 0.99 3H,s,CH3-19 1.90 3H,s,NAc 2.03,2.12,2.15 12H,3s,OAc×4 2.60 1H,dd,J=4.5および12.6Hz,3-Heq 3.78 3H,s,COOMe 4.86 1H,m,4-H β体の物理恒数 Mass(FD)m/z860(M++1) 1H NMR CDCl3 δ(TMS) 90MHz 0.66 3H,s,CH3-18 0.83および0.87 6H,CH3-26,CH3-27 0.90 3H,d,J=4.5Hz,CH3-21 1.00 3H,s,CH3-19 1.86 3H,s,NAc 2.00,2.03,2.06および2.11 12H,4s,OAc×4 2.53 1H,dd,J=4.5および12.6Hz,3-Heq 3.78 3H,s,COOMe 実施例2 5−アセトアミド−2−O−アセチル−(5−コレステ
ン−3−β−イル)−3,5−ジデオキシ−α−D−グ
リセロ−D−ガラクト−2−ノニュロピラノソン酸の合
成 実施例1で得られた化合物(α体)をメタノール2m
に溶解し、これにINの苛性ソーダ溶液3mを加え、
室温で一夜攪拌した。反応液に水2mを加え、ダウエ
ックス(Dowe-X)50で中和後、微量の沈殿を瀘去し、瀘液
を減圧乾固した。白色粉末の標題化合物31.4mg(79.7%)
を得た。
Physical constant of the title compound Mass (EI) m / z859 (M + ), 800 (M + -59) 1 H NMR CDCl 3 δ (TMS) 90MHz 0.68 3H, s, CH 3 -18 0.84 and 0.87 6H, CH 3 -26, CH 3 = 27 0.90 3H.d, J = 4.5Hz, CH 3 -21 0.99 3H, s, CH 3 -19 1.90 3H, s, NAc 2.03,2.12,2.15 12H, 3s, OAc × 4 2.60 1H, dd, J = 4.5 and 12.6Hz, 3-Heq 3.78 3H, s, COOMe 4.86 1H, m, 4-H Physical constant of β body Mass (FD) m / z860 (M + +1) 1 H NMR CDCl 3 δ (TMS) 90MHz 0.66 3H, s, CH 3 -18 0.83 and 0.87 6H, CH 3 -26, CH 3 -27 0.90 3H, d, J = 4.5Hz, CH 3 -21 1.00 3H, s, CH 3 -19 1.86 3H, s, NAc 2.00,2.03,2.06 and 2.11 12H, 4s, OAc × 4 2.53 1H, dd, J = 4.5 and 12.6Hz, 3-Heq 3.78 3H, s, COOMe Example 2 5-acetamido-2-O-acetyl- (5-cholesten-3-β-yl) -3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosonic acid Synthesis The compound (α-form) obtained in Example 1 was added with 2 m of methanol.
Dissolved in, add 3m IN caustic soda solution to it,
Stir overnight at room temperature. 2 m of water was added to the reaction solution, neutralized with Dowe-X 50, a trace amount of precipitate was removed by filtration, and the filtrate was dried under reduced pressure. 31.4 mg (79.7%) of the title compound as a white powder.
Got

上記と同様にして、実施例1で得られたβ体から標題化
合物の異性体であるβ体30.0mg(76.1%)を得た。
In the same manner as above, from the β-form obtained in Example 1, 30.0 mg (76.1%) of the β-form which was an isomer of the title compound was obtained.

標題化合物の物理恒数 1H NMR CDCl3 δ(TMS) 90MHz 0.71 3H,s,CH3-18 0.84および0.91 6H,CH3-26およびCH3-27 0.95 3H.d,J=4.5Hz,CH3-21 1.00 3H,s,CH3-19 2.01 3H,s,NAc 2.43 1H,dd,J=4.5および12.6Hz,3-Heq β体の物理恒数 1H NMR CD3OD δ(TMS) 90MHz 0.71 3H,s 0.86および0.92 6H,CH3-26およびCH3-27 0.95 3H,d,J=4.5Hz,CH3-21 1.00 3H,s,CH3-19 2.00 3H,s,NAc 2.39 1H,dd,J=4.5および12.6Hz,3-Heq Physical constant of the title compound 1 H NMR CDCl 3 δ (TMS) 90MHz 0.71 3H, s, CH 3 -18 0.84 and 0.91 6H, CH 3 -26 and CH 3 -27 0.95 3H.d, J = 4.5Hz, CH 3 -21 1.00 3H, s, CH 3 -19 2.01 3H, s, NAc 2.43 1H, dd, J = 4.5 and 12.6Hz, 3-Heq Physical constant of β body 1 H NMR CD 3 OD δ (TMS) 90MHz 0.71 3H, s 0.86 and 0.92 6H, CH 3 -26 and CH 3 -27 0.95 3H, d, J = 4.5Hz, CH 3 -21 1.00 3H, s, CH 3 -19 2.00 3H, s, NAc 2.39 1H, dd, J = 4.5 and 12.6Hz, 3-Heq

───────────────────────────────────────────────────── フロントページの続き (72)発明者 志鳥 善保 東京都武蔵野市中町3−5―24―408 (56)参考文献 特開 昭57−193496(JP,A) ─────────────────────────────────────────────────── ─── Continuation of front page (72) Inventor Yoshiho Shitori 3-5-24-408 Nakamachi, Musashino-shi, Tokyo (56) Reference JP-A-57-193496 (JP, A)

Claims (2)

【特許請求の範囲】[Claims] 【請求項1】下記の一般式〔I〕で示されるシアル酸誘
導体。 式中、R1及びR2はいずれか一方がカルボキシル基又は
メトキシカルボニル基であり、他方が下記の式 で示される基であり、R3は水素又はアセチル基であ
る。
1. A sialic acid derivative represented by the following general formula [I]. In the formula, one of R 1 and R 2 is a carboxyl group or a methoxycarbonyl group, and the other is the following formula And R 3 is hydrogen or an acetyl group.
【請求項2】一般式〔II〕 で示される化合物をコレステロールと反応せしめ、次い
で必要により加水分解することを特徴とする下記の一般
式〔I〕で示されるシアル酸誘導体の製造方法。 式中、R1及びR2はいずれか一方がカルボキシル基又は
メトキシカルボニル基であり、他方が下記の式 で示される基であり、R3は水素又はアセチル基であ
る。
2. General formula [II] A method for producing a sialic acid derivative represented by the following general formula [I], which comprises reacting a compound represented by the formula (1) with cholesterol and then hydrolyzing the compound if necessary. In the formula, one of R 1 and R 2 is a carboxyl group or a methoxycarbonyl group, and the other is the following formula And R 3 is hydrogen or an acetyl group.
JP6974185A 1985-04-02 1985-04-02 Sialic acid derivative and method for producing the same Expired - Lifetime JPH064671B2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP6974185A JPH064671B2 (en) 1985-04-02 1985-04-02 Sialic acid derivative and method for producing the same

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP6974185A JPH064671B2 (en) 1985-04-02 1985-04-02 Sialic acid derivative and method for producing the same

Publications (2)

Publication Number Publication Date
JPS61243096A JPS61243096A (en) 1986-10-29
JPH064671B2 true JPH064671B2 (en) 1994-01-19

Family

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JP6974185A Expired - Lifetime JPH064671B2 (en) 1985-04-02 1985-04-02 Sialic acid derivative and method for producing the same

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Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2747967B2 (en) * 1993-07-23 1998-05-06 雪印乳業株式会社 Sialic acid powder
DE69616554T2 (en) * 1995-06-23 2002-07-11 Mitsubishi Chem Corp SIALIC DERIVATIVES
US6337390B1 (en) 1996-05-16 2002-01-08 Nissan Food Products Co., Ltd. Compounds comprising sulfated nonulonic acid having antiviral activity
US6444649B1 (en) 1998-04-10 2002-09-03 Mitsubishi Chemical Corporation Solid dispersion containing sialic acid derivative

Also Published As

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JPS61243096A (en) 1986-10-29

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