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    • 专利摘要:
    An alkyl-ketohexopyranoside derivative having pharmacological actions such as antiallergic actions, represented by the following general formula <IMAGE> wherein R is an alkyl group having at least 3 carbon atoms, the derivatives excluding the D-fructose derivative wherein R is n-propyl group.
    公开号:SU978732A3
    申请号:SU802928971
    申请日:1980-05-22
    公开日:1982-11-30
    发明作者:Нода Каньи；Накагава Акира；Харагучи Ясуси；Еда Коичиро；Хирано Минехико；Ничиока Итсуо；Иаги Акира
    申请人:Хизамицу Фармасьютикал Ко.,Инк (Фирма)；
    IPC主号:
    专利说明:

    (3) METHOD FOR OBTAINING DERIVATIVES OF ALKYL-KETHOXYPHYRANOSIDE
    one
    This invention relates to a process for the preparation of new ketohexopyranose derivatives. possessing valuable pharmacological properties.
    The purpose of the invention is to obtain new useful compounds expanding the arsenal of means of influencing a living organism.
    The goal is achieved based on the known reaction of the preparation of ethers 1D by the method of obtaining alkyl ketohexopyranoside derivatives of the general formula
    where R is H-propyl, isopropyl, N-bu, til, N -pentyl, isopentyl, N -hexyl or isohexyl, with the exception of the corresponding derivative D.-fructose
    8 where R is I-propyl, according to which ketohexose of the formula
    % JiO,)
    (AND)
    f
    V-lliHp
    . SNRON
    but to
    subject to jco interaction; alcohols, Q of general formula (III) ROH, where R is the indicated values, in the presence of mineral acid, at a temperature of from 20 to 80 ° C for 0.5-2t h. Alkyl ketohexopyranoside derivatives have valuable pharmacological action, such as antiallergic action, markedly attenuating allergic reactions in the body, and the anticancer effect, due to this, are of interest as potentially useful and promising from the point of view of possible industrial production of medical compounds. The resulting compounds are capable of selectively inhibiting the production of reagins, i.e., antibodies or immunoglobulins (ig, E) due to allergic diseases, while not inhibiting the production of immunoglobulins (igG, GdM) that determine immune responses in normal human organisms. In addition, some of the proposed compounds have been found to have the ability to accelerate (activate) the production of immunoglobulins (igG, 1dM). The compounds are isolated and purified in a barely fine way. After completion of the reaction, the resulting reaction mixture was slowly introduced with stirring into the aqueous ammonia solution to neutralize, and the precipitate thus formed was then distilled off. The filtrate thus obtained is concentrated under reduced pressure, and the viscous mass remaining as a result of concentration is subjected to purification, freeing it from undesirable impurities. Removal of these undesirable substances is achieved, for example, by treating the residue viscous mass with ethyl acetate, saturated with water, using a silica gel chromatography column, or by treating the viscous residue with activated carbon or water-alcohol liquid mixture. The mass freed from undesirable substances is concentrated and dried under reduced pressure, resulting in a targeted alkyl ketohexopyranoside derivative in the form of crude (raw) crystals. The crude crystalline substance thus obtained is then recrystallized from ethanol or a mixture with diethyl ether, as a result of which target compound (1) is obtained, which is a stable crystalline substance with a bitter taste and no odor. The target compounds thus obtained are listed in the table below.
    (IS)
    dH, oH
    n
    CH (CH2) CH3
    sn sn.sn
     SN
    (la)
    СН2 (СН2) СН СН. СНлНН сн CHj (CH2) CH
    -138,1
    -130,0
    157-158
    -123.2
    130-131 120-122 130-132 -131.0 -120.0
    (1b)
    sn

    sn.
    (1b)
    CH (
    sn
     (1b)
    SNOCH
    cn CH2 (CH2) cCH CHj (CH2) 4CH Example T. 10.0 g of D-fructose are added to a 0.2% solution of hydrogen chloride in n-butyl alcohol and the mixture is kept at room temperature for continuous reaction and stirring for 2 hours. h, after which the reaction mixture is slowly introduced with stirring into a 251% aqueous ammonia solution to neutralize the precipitate thus formed is filtered off and the filtrate is concentrated by evaporation under reduced pressure to obtain a yellow colored substance, The second was dissolved by heating in water with saturated ethyl acetate and then freed from insoluble substances by filtration. The filtrate thus obtained is evaporated to dryness in vacuo, then dried under reduced pressure, and the resulting dried substance is recrystallized from a ethyl acetate, thus obtaining 5.5 g of a crude crystalline product. Received so
    Table continuation
    98-99
    -73.2
    k6-k7
    -60.2 ° 79-80 92-93.  72-73 CH, 77-78 -70. 1 -65.6 -77. 5, the crude (unwashed) crystalline product is recrystallized from ethyl alcohol to give 3. 7 g of H-butyl p-O-fructopyranoside in the form of colorless needle-like crystals with m. square  1t7-1 9 C and the following characteristics.  Parting optical rotation cfc -138.1 ° Calculated,%: C 50.83; H 8.53.  C n fifOf Found,%: C 50. 79; H 8.5.  Example 2  KMOG 0.2% aqueous solution of hydrogen chloride in isobutyl alcohol was added 10.0 g of 0-fructose, and the resulting mixture was left under stirring for 2 hours at room temperature for reaction, after which the reaction mixture was slowly and carefully mixed to neutralization with a 25%, aqueous solution of ammonia.  The precipitate formed in this way is filtered to obtain a filtrate, which is concentrated by evaporation under reduced pressure until a viscous, yellow-colored substance is obtained in the residue.  The substance thus obtained is dissolved by heating in ethyl acetate; water, and the solution is filtered to remove insolvency. impurities.  The filtrate thus obtained is concentrated and dried under reduced pressure, whereby a dried product is obtained, which is quenched from ethyl acetate, to obtain 5.0 g of a crude crystalline product.  The crude crystalline product thus obtained was recrystallized from ethyl alcohol to obtain 3.5 g of isobutyl-B-O-fructopyranoside in the form of white needles having T.  pl, 157-158 p.  Specific optical rotation od jj.  -1 30.0.  Its calculated%: C 50.83; H 8.53; Found: C 50.81; H 8.52 Example 3.  To 85 g of 0, a solution of hydrogen chloride in H-foam (n-amyl) alcohol was added 10.0 g of D-fructose and left at room temperature and stirring for 2 hours.  After that, the reaction mixture is slowly and carefully mixed to neutralize with an aqueous solution of ammonia.  The precipitate formed in this way is separated by filtration, and the filtrate is concentrated by evaporation under reduced pressure to obtain a viscous, yellow-colored substance, which is dissolved in water-saturated ethyl acetate under heating.  The resulting solution is filtered to separate the undissolved impurities, and the collected filtrate is concentrated to vacuum to dryness and recrystallized from ethyl acetate, to obtain 5.2 g of crude crystalline product.  The crude crystalline product thus obtained was recrystallized again from ethyl alcohol, eventually obtaining 3.5 g of the desired H -pentyl-J-O-fructopyranoside in the form of colorless needle crystals having a volume of t.  square  130-131 C.  Specific Optical Investigations Saturation pi j -123.2 ° Calculated,%: C 52.78; H 8.86 And Found,%: C 52.80; H 8.84.  Example i.  10.0 g of D-fructose was added to a g of 0.1% hydrogen chloride in isopentyl (isoamyl) alcohol, and the resulting mixture was stirred at room temperature to carry out the reaction for 2k h, after which the reaction mixture was slowly and carefully mixed with aqueous ammonia solution (with stirring) to neutralize.  The precipitate thus formed is filtered off and the filtrate is concentrated under reduced pressure to leave a viscous, yellow colored substance, which is dissolved by heating in ethyl acetate saturated with water.  The resulting solution is filtered to remove undissolved substances, the filtrate is concentrated and dried under reduced pressure.  The residue obtained is recrystallized from ethyl acetate, whereby 2 g of crude (crystalline) substance is obtained.  The crude crystalline product thus obtained was recrystallized from ethyl alcohol, resulting in a total of 2.7 g of the desired isopentyl- (-0-fructopyranoside in the form of white needle-like crystals having m. square  120-122 “C.  Specific optical rotation,: 1 pOi -131. 0 °.  Calculated,%: C, 52.78; H 8.86 C 52.77; H 8.87 Found,%: 5.  10.0 g of D-fructose was added to 570 g of a 0.05% solution of hydrogen chloride in H-hexyl alcohol and the mixture was stirred at room temperature for 2 hours.  After completion of the reaction, the resulting reaction mixture is slowly and carefully mixed to neutralize with an aqueous solution of ammonia.  The resulting mass is filtered to remove the precipitate formed and to obtain a filtrate.  The filtrate thus obtained is concentrated in vacuo to leave a viscous, yellow-colored residue, which is dissolved in ethyl acetate saturated with water, with heating, and the resulting solution is filtered.  to remove insoluble impurities from it.  The filtrate thus obtained is concentrated and dried under reduced pressure, the resulting dry substance 9 is recrystallized from ethyl acetate to give 4.6 g of a crude crystalline product, which is recrystallized AND 3 of ethyl alcohol.  In the end, get 3.0 g of the target H-hexyl-p-0-f | euktopyranoside in the form of a white, powdery crystalline substance having t.  square  131-132 C.  Specific optical rotation ob1 J) i -120.0 °.  Calculated,%: C 5t, 53; H 9.15; Found: C 5.50; H 9.16.  Example 6 To 335 g of propyl alcohol containing sulfuric acid in the amount of 0.05 per alcohol, add 10.0 g of D-sorbent, and the mixture obtained is stirred at 15 hours.  After completion of the reaction and cooling, the reaction mixture is slowly and carefully mixed to neutralize with a 25% aqueous solution of ammonia.  The resulting n-3 mass is filtered to remove the precipitate formed and the filtrate is obtained.  The filtrate thus obtained is concentrated under reduced pressure to obtain a viscous, tanned syrup in the residue.  The syrupy residue thus obtained is dissolved in water, activated carbon is added to the solution, and the mixture is stirred for 20-30 minutes, then filtered to separate the activated carbon, which is washed on the filter with water, suspended in ethyl alcohol and stirred at 20-30 minutes for desorption or elution of adsorbed material from it.  This slurry is then filtered to remove the activated carbon and obtain a filtrate.  The filtrate thus obtained is concentrated and dried under reduced pressure to obtain a light yellow Solid which is recrystallized from a mixture of ethyl alcohol and diethyl ether to give 8.5 g of the desired n-Piopyl - (- 1-sorbopyranoside as white powder of different crystalline matter, having t.  P .  .  Specific optical rotationGOL-77, 3.  2 Calculated,%: C fR, 6A; H 8.16 Cp H, g06 Found:% C it8.62; H 8.17.  Example 7  KjIO g of H-butyl alcohol containing sulfuric acid in the amount of 0.05 per alcohol is added 10.0 g of L-copbose and the resulting mixture is stirred with n) and 70 ° C for 15 h.  After cooling, the reaction mixture is slowly and carefully mixed to neutralize with aqueous ammonia solution.  Then all the resulting mass is transferred to a filter and filtered to remove a precipitate and obtain a filtrate.  The filtrate thus obtained is concentrated under reduced pressure to obtain a viscous, yellow-brown syrupy residue, which is dissolved in water.  Activated carbon is added to this solution, the resulting slurry is stirred for 20-30 minutes and then filtered to separate the activated carbon.  The filtered activated carbon is washed with water and suspended in ethyl alcohol.  The resulting suspension is stirred at a temperature of about 50 ° C for 20-30 minutes in order to wash out the adsorbed substances on it from the activated carbon, and then filtered to remove the activated carbon and obtain the filtrate.  The filtrate thus obtained. concentrated and dried in vacuo to give a residue a light yellow solid, which is recrystallized from a mixture of ethyl alcohol and diethyl ether.  A total of 9.3 g of the desired H-butyl-in -L-sorbopyranoside is obtained in the form of a white, powdered, crystalline product, having t.  square   WITH.  Specific optical rotation with / 3tz -73; 2.  Calculated, I: C 50.83; H 8.53 6 „„, Found,: C 50.85; H 8.5.  Example 8  K4lOr of isobutyl alcohol containing sulfuric acid in an amount of 0.053, calculated as alcohol, was added 10.0 g of L-adsorbed and the mixture was left to react for 15 hours under continuous stirring and heating at 70 ° C.  After completion of the reaction and cooling of the reaction mixture, it is carefully mixed for neutralization with an aqueous solution of ammonia.  Then all the resulting mass is filtered.  The filtrate thus obtained is concentrated under reduced pressure to obtain a viscous yellow-brown residue, which is dissolved in water and treated with activated charcoal.  The resulting suspension is stirred for 2030 minutes, then filtered to separate activated carbon.  The filtered activated carbon is washed with water and suspended in ethyl alcohol.  The prepared suspension of activated carbon in the alcohol-water mixture is stirred at a temperature of about 2030 minutes in order to wash out the adsorbed substances on it, and then filtered to separate the coal and obtain a filtrate.  The filtrate obtained in this way is concentrated and dried under reduced pressure to give the residue. light yellow solid product that recrystall. lysing from a mixture of ethyl alcohol and diethyl ether to obtain 9.1 of the desired isobutyl-o6-1-sorbopyranoside as a white crystalline powder having m, mp, 79-80 ° t.  Specific optical rotation with: -BO, 2 1: C 50.83; H 8.53. Calculated. C (oCh2oC C 50.86; H 8.5.  An example was found. To 485 g of an AND -pentyl (n-amyl) alcohol containing sulfuric acid in an amount of 0.05, based on the alcohol taken, was added 10.0 g of 1-sorbose, and the mixture was stirred at 70 ° C in for 15 hours  After cooling the reaction mixture, it is slowly and carefully mixed with an aqueous solution of ammonia.  The resulting mass is then filtered to remove the precipitate and to obtain a filtrate.  The filtrate thus obtained is concentrated under reduced pressure until a viscous, yellowish-brownish syrupy substance is obtained, which is dissolved in water, activated carbon is added to the solution and the suspension is stirred for 20-30 minutes.  After that, the activated carbon is separated by filtration, the filter cake is washed with water and suspended in 30% ethanol.  The suspension is stirred in this medium 2 at a temperature of about 50 ° C for 20-30 minutes, after which the mixture is filtered in order to separate the activated carbon and obtain a filtrate. This filter is concentrated and dried under Reduced pressure until a light solid appears in the residue, which is recrystallized from a mixture of ethyl alcohol and diethyl ether.  In the end, get 9, g of the target N -pentyl-o (, -i-sorbopyranoside in the form of a white powdered crystalline substance having t, mp, 92-93 C, Specific optical rotation about.  -70.1 Calculated,%: C 52.78; H 8.86, Found,%: C 52.81; H 8.85.  Example 10 To 485 g of isopentyl (isoamyl) alcohol containing sulfuric acid in an amount of 0.05, calculated on the taken alcohol, 10.0 g of L-sorbose was added, and the resulting mixture was stirred for reaction at 70 ° C for 15 h.  After cooling.  to room temperature, the resulting reaction mixture is slowly mixed to neutralize with an aqueous solution of ammonia.  Then all the resulting mass is transferred to a filter and filtered.  The resulting filtrate. concentrated under reduced pressure to obtain a viscous, yellowish-brown syrup-like residue which is dissolved in water, activated charcoal is added to the solution and the resulting suspension is stirred for 20-30 minutes, then filtered to separate the activated carbon.  The filtered activated carbon is washed with water, re-suspended in ethyl alcohol, and the resulting suspension is stirred in this medium at a temperature of about 50 ° C for 20-30 minutes.  Then the suspension is filtered.  This filtrate is concentrated and dried under reduced pressure until a light yellow solid remains, which is recrystallized from a mixture of ethyl alcohol and diethyl ether.  8.9 g of the desired isopentyl-2-1-sorbopyranoside were obtained in the form of a white powdery crystalline substance having m, mp, 7273 C, Specific optical rotation MD: -65 ,, Calculated, with 52.78; H 8.86 C Found:% C 52.62; H 8.89 Example 1.  To 57d, the rH-hexyl alcohol containing sulfuric acid in an amount of 0.05%, based on the alcohol taken, is.  10.0 g of L-, are added.  sorbose, the resulting mixture is stirred for reaction at 70 ° C for 15 hours.  After cooling the reaction mixture to room temperature, dl neutralization is slowly and carefully mixed with an aqueous solution of ammonia.  Then century) the resulting mass is transferred to a filter and filtered.  The resulting filtrate is concentrated under reduced pressure to obtain a viscous, yellowish-brown syrupy residue, which is dissolved in water, activated carbon is added to the solution and the resulting suspension is stirred for 20-30 minutes, then filtered.  The filtered activated carbon is washed with water and transferred to ethyl alcohol, which is stirred at a temperature of about 20-30 minutes.  The suspension is then filtered, the filtrate is concentrated and dried under reduced NOM pressure, resulting in a light yellow solid in the residue, which is recrystallized from a mixture of ethyl alcohol and diethyl ether, to obtain 8.0 g of the desired H-hexyl-o- 1-sorbopyranoside in the form of a whitish powdered crystalline substance having t.  square  77-78 C.  Specific optical rotation ocj Calculated, H: C 5.53; H 9.15; Found: C 5.55; H 9.17.  In each of these examples, the operation of concentrating the solutions is carried out / At a residual pressure of 20-30 mm RTS and a temperature of 60-70 C.  P . p 12  350 g of isopropyl alcohol containing hydrogen chloride in the amount of 0.2% of the alcohol is combined with 8.2 g of O-fructose and the resulting mixture is subjected to vigorous stirring, at H ° C for 5 h, after which the reaction mixture is slowly drained with ammonia water under stirring for neutralization.  The resulting precipitate is filtered off, and 2It the resulting filtrate is concentrated at. reduced pressure to obtain a yellow colored viscous substance, which is dissolved in ethyl acetate diluted with water with heating and then freed from insoluble substances by filtration.  The filtrate thus obtained is subjected to concentration and dried under reduced pressure, and the resulting dried substance is subjected to recrystallization from ethyl acetate to give "2 g of raw material, which is then recrystallized from ethyl alcohol to obtain 2.6 g of isopropyl-O-fructopyranoside as colorless needles crystals with t.  square  112-113 C.  Calculated%  C, 64; H 8.16 C o H gO 6 Found:% k8.66; H 8.1.  PRI me R 13.  10.0 g of 0-fructose is added to 170 g of 0.2% isoheylsilic alcohol containing hydrogen chloride and the whole mass is reacted with thorough stirring at 80 ° C for 0.5 h, after which the reaction mixture is slowly drained with 25% ammonia water for neutralization.  The resulting precipitate is filtered, the filtrate is concentrated under reduced pressure, and as a result, a viscous yellow substance is obtained.  Thus, the remaining substance is dissolved in dilute.  water with ethyl acetate when heated and filtered.  The filtrate obtained in this way is concentrated and dried under reduced pressure to obtain a dried substance, which is recrystallized from ethyl acetate to obtain A, O g of product; raw  The product thus obtained is recrystallized from ethyl alcohol to obtain 2.5 g of isohexyl-O-fructopyranoside as white needle crystals with m.  square  146-1 8 s.  Calculated,%: C 5.53; H 9.15; Found 5.51; H 9.15 K.  kSO g of isobutyl alcohol containing sulfuric acid in an amount of 0.05%, 10.0 g of L-coposes are added to form a mixture, which is reacted with stirring at 80 ° C for 6 hours.  After cooling, the reaction mixture.   .  9 merged with ammonia water until neutralized.  The whole mass of the filtrus was used to remove the precipitate obtained and the filtrate was obtained.  The filtrate thus obtained is subjected to concentration under reduced pressure in order to obtain a viscous, yellow-blue syrup-like residue.  The residue thus obtained is dissolved in water with activated carbon and stirred for 20-30 minutes. .  The whole mass is filtered, activated. the coal is washed with water, poured with 30% ethanol, stirred at 50 ° C for 20-30 minutes, then filtered.  The resulting filtrate under. Concentrate and dry under reduced pressure to give a light yellow solid. which is recrystallized from a mixed solvent consisting of ethyl alcohol and ether, resulting in a yield of 7.2 g. isobutyl-C6-1-sorbopyranoside as a white crystalline powder, having t.  square  7980 ° C.  Specific rotation (polarization plane) d. -60,  .  C 50.83; Calculated, H 8,53 С1оН2оОб С.  50.81; H 8.50.  Seen, Z: 15.  K 570 g of N-hexiphenol containing sulfuric alcohol.  0.0 g of L-sorbose was added in an amount of 0.05 g of acid to form, which was stirred at 60 ° C for 6 hours.  After cooling, the reaction mixture is stirred with ammonia water with stirring for neutralization.  The whole mass is filtered to remove a precipitate and a filtrate is obtained.  The resulting filtrate is concentrated under reduced pressure to give a viscous yellow brown syrup. good balance.  The residue thus obtained is dissolved in water with activated carbon, stirred for 20-30 min. And activated charcoal is filtered.  The activated carbon is rinsed with water and placed in 301 ethanol, where it is agitated for approximately 20–30 minutes in order to cause the adsorbed product to carbonize from the carbon and then filtered to obtain a filtrate.  2 The filtrate is concentrated and dried under reduced pressure to give a light yellow solid, which is recrystallized from a mixture of solvents, ethyl alcohol and ether, to give 6.4 g of H-hexyl-a: -1 sorbopyranoside as a white crystalline bed of sugar having t.  square  77-78 C.  The specific rotation (polarization plane) is about; -77.5.  Calculated,%: C 5.53; H 9.15; Found: C 54.51; H 9.1.  Example 16  10.0 g of D-fructose is added to 500 g of isobutyl alcohol containing 0.2 d chloride of drod to give a mixture that is thoroughly mixed at 50 ° C for 5 h.  After completion of the reaction, the resulting reaction mixture is slowly poured with 25% ammonia water for neutralization.  The precipitate is filtered off.  The resulting filtrate is concentrated under reduced pressure to give a yellow viscous substance, which is dissolved in ethyl acetate with water and heated with heat and filtered to remove a precipitate.  The filtrate thus obtained is subjected to concentration and dried under reduced pressure.  The dry substance thus obtained is recrystallized from ethyl acetate to obtain.  4, G: g raw product, which is then recrystallized from ethyl alcohol to obtain 2.6 g of isobutyl-B-0-fructopyranoside as a white crystalline powder, having t.  square  157-158 ° C.  Specific rotation (polarization planes). -130.0 °.  Elemental analysis.  Molecules. formula Calculated; C 50.83; H, 8.53 CfoH2o06; Found: C, 50.84; H 8.50.  Example 17  10.0 g of L-sorbose are added to 520 g of isopentyl alcohol containing sulfuric acid (f) in an amount of 0.05, the mixture is reacted with stirring at 80.  C for 0 ,.  After cooling, the resulting reaction mixture is poured into ammonia water for neutralization.  The precipitate is filtered off.  The obtained filtrate is concentrated under reduced pressure to obtain
    权利要求:
    Claims (1)
    [1]
    The claims ί A method of obtaining derivatives of al. kilketohexopyranoside of the general formula "
    but And where R is H-propyl, isopropyl, H “butyl, isobutyl, H-pentyl, isopentyl, 25 Ή-hexyl or isohexyl, with the exception of: the corresponding derivative of D fructose, in which R is H-propyl, characterized in that ketohexose formula
    OH n is reacted with an alcohol of the general formula to give a viscous yellow syrupy residue, which in turn is dissolved in ethyl acetate diluted with water under heating and the precipitate is filtered off. The resulting filtrate is concentrated and dried under reduced pressure to give 45 material which was recrystallized from ethyl acetate to obtained: cheniem 4.4 g of crude product which was
    ROH, where R - has the indicated values, in the presence of a mineral acid at 20-80 ° C for 0.5-24 hours.
    Sources of information taken into account during the examination of G. Buhler K. and Pearson D. Organic syntheses, M., 1973, part 1, chap. 6, p. 348.
    Editor A. Vlasenko Compiled by G. KonnovaTehred 3.Pali Corrector. Ponomarenko
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    同族专利:
    公开号 | 公开日
    AU5861580A|1980-11-27|
    CA1141761A|1983-02-22|
    ATA278880A|1982-03-15|
    DE3019221A1|1980-12-04|
    AT368755B|1982-11-10|
    AU529742B2|1983-06-16|
    FR2457300B1|1983-06-24|
    NL8002981A|1980-11-25|
    IT1140976B|1986-10-10|
    ES492194A0|1981-04-01|
    SE8003815L|1980-11-24|
    GB2052485B|1983-04-07|
    JPS55154991A|1980-12-02|
    ZA803076B|1981-06-24|
    IT8022265D0|1980-05-22|
    US4395405A|1983-07-26|
    ES8104321A1|1981-04-01|
    FR2457300A1|1980-12-19|
    CH647531A5|1985-01-31|
    GB2052485A|1981-01-28|
    AR225310A1|1982-03-15|
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    法律状态:
    优先权:
    申请号 | 申请日 | 专利标题
    JP6476979A|JPS55154991A|1979-05-23|1979-05-23|Beta-d-fructopyranoside derivative|
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