• 专利附录
  • 专利说明
  • 权利要求
  • 类似技术
  • 同族专利
  • 引用文献
  • 法律状态
  • 优先权
    • 专利摘要:
    Disclosed are a pharmaceutically active sugar molecule and a synthesis method thereof. The sugar molecule has a structure as shown by formula (I) or (II) and can be used for synthesizing a sulfonated sugar molecule, so that it can be further applied to research on E. coli pathogenesis. The synthesis method provided by the present invention is simple, convenient and easy to operate, and can be used for synthesis of a variety of sugar molecules.
    公开号:ES2646628A2
    申请号:ES201790034
    申请日:2016-03-04
    公开日:2017-12-14
    发明作者:Yulong SHAN
    申请人:Huaian Peaks Biological Science And Tech Co Ltd；Huaian Peaks Biological Science And Technology Co Ltd；
    IPC主号:
    专利说明:

    DESCRIPTION

    Pharmaceutically active sugar molecule and its method of synthesis.

    Object of the invention 5

    The present invention, as expressed in the statement herein refers to a pharmaceutically active sugar molecule and its method of synthesis, whose object is to be able to serve as an important means for the chemical synthesis of sulfonation sugar molecules, further applying the mechanism of The pathogenicity for the investigation of Escherichia coli, the invention offers a simple, convenient and easy-to-use synthesis method that can be used for the study of the molecular structure of coliform bacilli, as well as being able to synthesize many sugar molecules and The synthesis of molecules provided by the invention can be used for different drug preparation and development activities. fifteen

    Scope

    The field of application falls within the field of chemical technology in medicine, especially as regards active sugar molecules for 20 medications.

    Background of the invention

    Escherichia coli is the common bacterium, and usually appears in the human body and animal body. Most bacteria are harmless, but some species harmful to the human body, such as H4 Escherichia coli in Germany and France caused 50 deaths.

    FebF is the final F18 pili escherichia coli, when the FebF sugar molecule captures the intestinal mucosa in 30, it can cause diseases such as diarrhea or edema. FebF is often found with lactose acetyl sulfonation and sulfonation with lactose amines, but the specific binding has not yet been confirmed.

    For the study of the structure of carbohydrates in combination of substances, the molecular structure of glucose is the synthesis of the different needs of sulfonation.

    In order to solve the exposed problems, the activity of the synthesis of sugar molecules of the present invention can be used for application to important products such as the synthesis of sulfonating sugar molecules, which is applied in the pathogenesis of escherichia coli , and said synthesis of molecules provided by the invention can be used for different drug preparation and development activities.

    Explanation of the invention

    Specifically, what the present invention advocates is a pharmaceutically active sugar molecule and its method of synthesis, a sugar molecule constituting the active drug, in the form of (I) (II) of the sample structure, activity of the sugar molecule can be used to synthesize a sulfonation sugar molecule, which is applied in the pathogenesis of escherichia coli.




    Among them, R1 and R2 independently from one or more Ra substituted C1-20 sub alkyl; each independent Ra selected from H, alkyl, oxygen alkoxy, heterocyclic alkyl, aromatic alkyl, aryl blending alkyl, halogen or amino, wherein the base of said heterocyclic alkyl and aryl blending alkyl contain 1- 5 independent chosen from N, O and S heteroatoms.

    As an example, R1, R2 independently from one or more substituted C1-20 alkyl Ra; each independent Ra selected from H, C1-10 alkyl, 3-10 yuan heterocyclic alkyl, C6-10 aryl alkyl, 5-10 yuan alkyl of heterocyclic aromatic, F, Cl, Br, I or amino, where the base of said heterocyclic alkyl and alkyl blending alkyl contain 1-5 independent selected from N, o and S heteroatoms.
     fifteen
    In cases of more optimized execution, R1, R2 independently from one or more Ra substituted sub alkyl; C1-20 each independent Ra selected from H, methyl, ethyl, propyl, isopropyl, benzene ring, substituted benzene ring, 5-6 yuan heterocycles, 5-6 yuan heteroaryl elements, F, Cl, Br, I or NH2, wherein the base of said heterocyclic alkyl and aryl mixture alkyl contain 1 - 3 independent selected from N, O and S heteroatoms.

    In some cases the invention, R1, R2 of independent methylene selected to Ra from the substitution of one or more, each independent Ra selected from H, methyl, ethyl, the benzene ring, the substituted benzene ring or NH2. 25

    As an example, so that the invention (I) or (II) of compounds that can be compounds from the following:

     30

    The invention also provides type (I) or (II) which is shown in the form of synthesized compounds, the process consists of the following reactions:


      5
    - Among them, R1, R2 independently with the above definition;

    - X is a halogen.

    - As a practical example, the method of the invention of preparation consists of the following 10 reaction steps:

    one). In the presence of bases, the manner (1) of the reaction compounds with anhydride, the formula (2) of the compounds is obtained.
     fifteen
    2). The way (2) of reaction of alcohols with generation halides, obtains the way of (3) milk glycoside compound.

    3). The manner (3) of reactions of compounds and azides, formula (4) of the compounds shown is obtained. twenty

    4). The way (4) of the hydrolysis of compounds, the formula (5) of the compounds shown is obtained.

    5). The manner (5) of acetals or ketals compounds and reactions, formula 25 (I) or (II) of the compounds shown is obtained.

    - Among them, step 2) halogens in halogenated alcohols, F, Cl, Br or I; The formation of alcohols such as C1-10 alkyl, acetic anhydride as a catalyst.

    Step 3) of azides, preferably sodium azide or potassium azide 1 azide;
     5
    R1, R2 independently with the above definition; X is a halogen.

    Define and Explain the Term

    Unless otherwise indicated, when "compounds of this invention are used in the document" or when "the invention of the compounds" encompasses type (I) and (II) shows all compounds.

    The term "halogens" fluorine, chlorine, bromine and iodine.
     fifteen
    The term "C1-20 alkyl" should be understood as a referenced representation of 1-20 saturated carbon atoms with direct-linked or monovalent branched chain hydrocarbons, preferably C1-10 alkyl. "C1-6 alkyl" should be understood as a preferred representation 1, 2, 3, 4, 5 or 6 carbon atoms or branched chain saturated hydrocarbons with a price, for example, methyl, ethyl, propyl, butyl, amyl, 20 hexyl, isopropyl alcohol, isobutyl base, butyl base, tert-butyl, isoamyl, 2-methyl butyl, 1-methyl butyl, 1-ethyl propyl, 1,2-2-methyl propyl, neopentyl ,, 4-Amyl methyl, 3-Amyl methyl, 2-Amyl methyl, 1-Amyl methyl, 2-Butyl ethyl, 1-Butyl ethyl, 3,3-Dimethyl butyl, 2,2-Dimethyl butyl, 1,1- Butyl dimethyl, 2,3-Butyl dimethyl, 1,3-Butyl dimethyl or 1,2-Dimethyl-butyl or Isomers thereof. In particular, the group has 1, 2, 3 or 4 carbon atoms ("C1-4 alkyl"), for example, methyl, ethyl, propyl, butyl, isopropyl, isobutyl base, butyl SEC, butyl tert , more particularly, said group has 1, 2 or 3 carbon atoms ("C1-3 Alkyl"), for example methyl, ethyl, N-propyl or isopropyl.

    The term "sub alkyl" refers to any direct or branched chain 30 bivalent hydrocarbons, "C1-20 sub alkyl" should be understood as preferred representation is 1-20 saturated carbon atoms direct link branched chain hydrocarbons or Bivalent, preferably C1-10 sub-alkyl, should be understood as the preferred representation with 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10 saturated carbon atoms of direct or bivalent branched chain hydrocarbons, which includes 35 - (CH2) 1-10- sub alkyl, in particular -CH2-, - (CH2) 2-, - (CH2) 3-, - (CH2) 4-, - (CH2) 5-, - (CH2 ) 6- O -CH (CH3) -, -C (CH3) 2-, -CH (C6H5) -, -CH (CH2CH3) - etc ..

    The term "ring heterocyclic ring or double ring of monovalent saturated hydrocarbons means, it contains 1-5 independent selected from heteroatom N, O and S, preferably" 3-10 alkyl heterocyclic yuan ". The term "3-10 yuan heterocyclic alkyl" ring or double ring of monovalent saturated hydrocarbons means, contains 1-5, preferably from 1-3 selected from heteroatoms N, O and S.

    The term "C6-10 aromatic alkyl", should be understood as preferred representation 45 with 6-10 aromatic carbon atoms aromaticity or part of a ring. It should be understood as a preferred representation with 6, 7, 8, 9, 10 carbon atoms or part of an aromatic aromatic ring.

    The term "5-10 yuan heteroaryl alkyl aromatics" should be understood as a monovalent ring, double system or tricyclic aromatic rings: It has 5-10 ring atoms and contains 1-5 independent selected from N, O and S heteroatoms .


    The beneficial effect of the invention:

    1. The invention of the sugar molecule can serve as an important intermediate for the chemical synthesis of sugar molecules sulfonylurea, the pathogenicity mechanism for the investigation of escherichia coli. 5

    2. The compounds of the invention always have azido as a connected group of the gene mission, the molecular structure of the reaction with other bonds can be much better, it can be used to study the molecular structure of coliform bacilli, it is of great importance in the development of medicines. 10

    3. For the synthesis of sugar molecules provided by the invention it can be used for different drug preparation activities, and the operation is simple and convenient.
     fifteen
    Application specific realization

    In this invention, a pharmaceutically active sugar molecule and its synthesis method, compounds and its more detailed preparation and application method of the note are specified below. The following examples only as an example to illustrate and then the invention, and should not be construed as limiting the scope of protection of the invention. The contents of the invention of the technology that is included in the application within the limits of this invention that it intends to protect.

    Unless otherwise indicated, the use of the materials and reagents of incarnation 25 are sold in the goods market.

    Application Example 1: The Activity of Sugar Molecules (001) Preparation
     30
    1.1 Preparation of Compounds (2)

    Take the anhydrous sodium acetate (2 eq, 25.0 g, 0.31 mol) and acetic anhydride (10. 7 eq, 175 ml, 1.85 mol) from heating the mixture to reflux temperature, then one by one to compounds 1 (D - Lactose, 1 eq, 50.0 g, 0.15 mol), follow 30 35 minutes reflux heating reaction, the solution reaction in 500 ml of ice water in the stirring overnight, Solids separation the washing, filtering, vacuum drying after 600 ml of ethanol by recrystallization, to achieve product objective 2 (80.6 g, 81%).
     40
    The magnetic resonance spectroscopy of the data are as follows:

    1H-NMR2. (500 MHz, CDCl3 = 7.31 ppm): δ = 5.66 (d, 1H, H-1, J1.2 = 8.4 Hz), 5.33 (dd, 1H, J = 1.2Hz, J = 3.6 Hz H-4 ') , 4.46 (d, 1H, J = 7.6 Hz, H-1 '), 4.42 (d, 1H, H-6' a), 4.13-4.04 (m, 3H, H-5 ', H-6A, H- 6'B), 3. 88-3.85 (m, 2H, H-4 ', H-6b) 2.14, 2.10, 2.08, 2.05, 45 2.04, 2.02, 2.01, 1.95 (Bs, 24H, 8CH3) ppm:

    13C-NMR (125 MHz, CDCl3 = 77.16): δ = 170.48, 170.44, 170.26, 170.18, 169.74, 169.68, 169.14, 168.98 (8C, BC = O), 101.68 (C-1 '), 91.67 (C-1 ), 75.81, 73.63, 72.76, 71.09, 70.87, 70.65, 69.14, 66.74, (8C), 61.87 (C-6), 60.98 (C-6 '), 20.95, 20.93, 20.87, 20.75, 20.73, 50 20.71, 20.62, 18.53 (CH3) ppm.



    1.2 Preparation of Compounds (3)

    Take compound 2 (1 eq., 10.0 g 14.7 mmol) and toluene rotate together after distillation, dissolve in DCM; 3-mcpd (2 eq., 2.5 mL, 29.4 mmol) and BF3.Et20 (2.5 eq, 4.7 mL, and 36.8 mmol) leave adhesion in reaction to the solution, the reaction of 5 nitrogen in the environment, the reaction mixture at room temperature for 3 hours, the reaction process by TLC (toluene / EtOAc, 1: 1) supervisory control; After the reaction, add the solution in ice water for 30 minutes; after mixing the stratification solution, with the saturation of the NaHCO3 organic layer and the saturation of water and salt, the distillation of pressure reduction; After separation of the crude product by silica, obtain milk with long glycoside chains (8.2 g, 82%).

    The magnetic resonance spectroscopy of the data are as follows:
    1H-NMR (500 MHz, CDCl3 = 7.31 ppm): δ = 5.33 (dd, 1H, J = 1.2 Hz, J = 4.4 Hz, H-4 '), 5. 15 14 (dd = t, 1H, H- 3), 5. 10 (dd, 1H, H-2 '), 4.94 (dd, 1H, J = 3.6 Hz, J = 10.4 Hz, H 3'), 4.87 (dd, 1H, J = 8.0 Hz, J = 9.6 Hz, H-2), 4.50-4.45 (m, 3H, H-1 ', H 6a, H-1), 4.14-4.04 (m, 3H, H-5', H-6a, H-6 'b), 3.96-3.91 (m, 1H, -OCH2a-), 3.88-3.84 (m, 1H, H-6b), 3.80-3.75 (dd = t, 1H, H-4), 3.69-3.55 (m , 4H, H-5, -OCH2b, -CH2N3), 2.14, 2.11, 2.05, 2.04, 2.03, 2.29, 1.95 (7s, 21H, -COCH3) ppm: 20

    13C-NMR (125 MHz, CDCl3 = 77.16 ppm): b = 170.50, 170.47, 170.27, 170.18, 169.86, 169.83, 169.19 (C = O), 101.21 (C1), 100.93 (C1 '), 76.4, 72.84, 72.80 , 71.79, 71.13, 70.83, 69.25 (7C), 66.74 (-OCH2CH2CH2Cl), 66.50, 62.11, 60.95 (3C), 41.43 (2C, -OCH2CH2CH2Cl), 32.29 (-OCH2CH2CH2Cl), 20.99, 20.93, 20.94, 20.82, 20.82, 20.82, , 20.76, 25 20.74 (CH3) ppm. MALDI-TOF MS: 737. 06 [M + Na] + ± 27 ppm.

    1.3 Preparation of Compounds (4)

    Take the compounds of 3 (1 eq, 4.0 g, 5.6 mmol) NaI (2 eq, 1.7 g, 11.3 mmol) dissolved in drying in DMF, heat at 50 ° C to stir for 1 hour; Then add NaN3 after the solution is heated to reaction 140 ° C 1 hour of reflux, the reaction in solution in ice water; then add EtOAc from the stratification, the separation of the organic phase, repeat the extraction and use of two etoac, the extraction phase twice after melting with salt water saturation, cleaning, distillation at 35 vacuum for obtain the subject and objective 4 (3.2 g, 80%).

    The magnetic resonance spectroscopy of the data are as follows:

    1H-NMR (500 MHz, CDCl3 = 7.31 ppm): δ = 5.39 (dd, 1H, J = 1.2 Hz, J = 3.6 Hz H-4 '), 5.23 40 (dd = t, 1H, H-3), 5.15 (dd, 1H, H-2 '), 5.00 (dd, 1H, J ~ 3. 6 Hz, J = 10.4 Hz, H-3'), 4.93 (dd, 1H, H-2), 4.55-4.50 (dd, 1H, H-6'a), 4.52 (d, 1H, H-1 '), 4.51 (d, 1H, H-1), 4.18-4.09 (m, 3H, H-5', H- 6a, H-6'b), 3.97-3.89 (m, 2H, H-6b, -OCH2a-), 3.83 (dd = t, 1H, J = 9.6 Hz, H-4), 3.66-3.59 (m, 2H, HS, OCH2b-), 3.41-3.36 (m, 2H, -CH2N3), 2.19, 2.16, 2.10, 2.09, 2.08, 2.01, 2.00 (7s, 21H, -CH3), 1.90-1.82 (m, 2H, -CH2CH2CH2N3) ppm; Four. Five

    13C-NMR (12S MHz, CDCl3 = 77.16 ppm): b = 170.40, 170.39, 170.19, 170.10, 169.80, 169.68, 169.12 (C = O), 101.22 (C1), 100.71 (C1 '), 76.38 (C-4 ), 72.89 (C-3), 72.81 (C-5), 71.79 (C-2), 71.12 (C-5 '), 70.83 (C-3'), 69.24 (C-2 '), 66.74 (C -4 '), 66.59 (-OCH2CH2CH2N3), 62.06 (C-6'), 60.93 (C-6), 48.08 (-OCH2CH2CH2N3), 29.11 50 (-OCH2CH2CH2N3), 20.98-20.64 (7 CH3) ppm. MALDI-TOF MS: 742.21 [M + Na] + ± 40 ppm.



    1.4 Preparation of Compounds (5)

    Take the compound of 4 (leq, 1.0 g, 1.38 mmol) methane soluble! drying (10 ml); After the addition of methane! sodium (1 M, 100 µl), the reaction solution at room temperature overnight, using the TLC reaction process (DCM / MeOH, 3: 1) for supervisory control; After the reaction, the reaction of adding liquid in Dowex H + of the ion exchange resin, stirring for 30 minutes; The neutralization reaction in the pH control monitoring, after the reaction, the filtrate exchange resin, cleaning with methane !, crystallization of a filtered liquid compound through the reduction of the pressure after distillation for get the yellow light of 5 (510 mg, 88%).

    The magnetic resonance spectroscopy of the data are as follows:
     fifteen
    1H-NMR (500 MHz, D2O = 4.80 ppm): δ = 4.49 (2xd, 2H, H-1 ', H-1), 4.04-3.98 (m, 2H), 3.95 (m, 1H), 3.84 (m , 1H), 3.81-3.77 (m, 3H), 3.5 (m, 1H), 3.70-3.65 (m, 3H), 3.64-3.60 (m, 1H), 3.58-3.54 (m, 1H), 3.48 (m , 2H), 3.35-3.31 (m, 1H), 1.93 (m, 2H, -OCH2CH2CH2N3) ppm;
     twenty
    13C-NMR (125 MHz, D2O, TMS = ppm): δ = 102.91 (C-1 '), 102.11 (C-1), 78.37, 75.33, 74.75, 74.36, 72.79, 72.50, 70.93, 68.52, 67.35 (- OCH2CH2CH2N3), 61.00, 60.06, 47.85 (-OCH2CH2CH2N3), 28.21 (-OCH2CH2CH2N3) ppm .: MALDI-TOF MS: 448.18 [M + Na] + ± 45 ppm.
     25
    1.5 The Activity of Sugar Molecules (001) Preparation

    In a round bottom flask of adhesion VO (OTf) 2 (0.05 eq, 40 mg), with drying of acetonitrile (1.77 mL) and the second oxy propane armor (10 eq., 2.9 mL), stir for 10 minutes to that the full solution, the solution is composed of light blue brown; 30
    Then add compounds of 5 (50 mg, 118 mmol), the reaction of two days at room temperature; TLC reaction process (EtOAc / MeOH, 4: 1) supervisory control; after the final reaction, the reaction of concentrated liquid after the separation column through silica gel to achieve the product target 001 (36 mg, 69%). 35



    Application Example 2: Sugar Molecule Activity (002) Preparation

    Taking the compound of 5 (1 eq., 1 g, 1.95 mmol) is dissolved in dry acetonitrile (10 5 mL), the adhesion of dimethyl benzaldehyde (2 eq., 800 µL) and the amount of camphor sulfonic acid catalyst ; The reaction mixture under conditions of 30 degrees at night; The reaction process by TLC (EtOAc / MeOH / water, 7: 2: 1) supervisory control, after the final reaction, the adhesion of triethylamine (330 µL), the reaction of the concentration of the silica gel solution from the separation column, obtain a compound 002 (1 g, 83%): MICRO-TOF MS: 513.325 [M +] ± 41 ppm.

    The invention through azido mission of genes to make the connection, the structure can be better with other molecules through the connection, for the synthesis of sugar sulfonation molecules, which applies the research mechanism of Escherichia coli 15 pathogenic, research in the field of technology applied to medicine. And the method can be used in the synthesis of various compounds, the operation is simple.

    The example of application of said above is only for the description of the invention of the best embodiment, it is not the idea and scope of the definition of the invention. Under the premise of not coming out in the design of this invention, the change and general improvement of people in the field of the invention of a technology, falls within the scope of the protection of the invention.
    25
    权利要求:
    Claims (10)
    [1]

    1. A pharmaceutically active sugar molecule and its method of synthesis, characterized in that it forms a structure of formula (I) or (II)
     5

    In which R1 and R2 are independently selected from C1-20 alkylene substituted by one or more Ra, each Ra independently selected from H, alkyl, alkoxy, heterocyclic, aryl, heteroaryl, halo or amino, in which the heterocyclic 10 and the heteroaryl contains from 1 to 5 heteroatoms independently selected from N, O and S.

    [2]
    2. A pharmaceutically active sugar molecule and its method of synthesis, according to claim 1, characterized in that R1, R2 are independently selected from C1-10 alkylene substituted by one or more Ra, each Ra is independently selected from H, C1-10 alkyl, 3-10 heterocyclic integrated, C6-10 aryl, 5-10 heteroaryl integrated, F, Cl, Br, I or amino, in which the heterocyclic and heteroaryl groups contain 1 to 5 wherein the base of said heterocyclic alkyl and aryl mixture alkyl contain 1-5 heteroatoms independently selected from N, O and S.

    [3]
    3. A pharmaceutically active sugar molecule and its synthesis method, according to claim 2, characterized in that R1 and R2 are independently selected from C1-10 alkylene substituted by one or more Ra. Each Ra is independently selected from H, methyl, ethyl, propyl, isopropyl, phenyl group, substituted benzene ring, 5-6 heterocyclic, 5-6 heteroaryl integrated F, Cl, Br, I or NH2, in which the groups of heterocyclic and heteroaryl contain 1-3 heteroatoms independently selected from N, O and S.
     30
    [4]
    4. A pharmaceutically active sugar molecule and its method of synthesis, according to claim 3, characterized in that R1 and R2 are each independently selected from methylene substituted by one or more Ra. Each Ra is independently selected from H, methyl, ethyl, benzene group, substituted benzene group or NH2. 35

    [5]
    5. A pharmaceutically active sugar molecule and its method of synthesis, according to claim 1, characterized in that it is selected from the following components:
     40


    [6]
    A pharmaceutically active sugar molecule and its method of synthesis, according to one of claims 1 to 5, characterized in that it comprises the following 5 reaction devices:

     10
    In which R1 and R2 each independently has the definition where defined in one of claims 1 to 4, X selected from halogens.
    [7]
    7. A pharmaceutically active sugar molecule and its method of synthesis, according to claim 5, characterized in that its preparation method consists of the following steps:
    one). The compound of the formula (1) reacts with an anhydrous acid, in the presence of a base to give a compound of formula (2).
    2). The compound of the formula (2) reacts with a halogenated alcohol to give a compound of formula (3).
     10
    3). The compound of formula (3) reacts with the acid to give a compound described in formula (4).
    4). The compound of the formula (4) is hydrolyzed to obtain a compound described in the formula (5). fifteen
    5). The compound of the formula (5) reactive with acetal or ketal, to obtain the compound of the formula (I) or (II).
    In which R1 and R2 are each independently defined as described in claim 5.
    X selected from halogens.

    [8]
    8. A pharmaceutically active sugar molecule and its method of synthesis, according to claim 7, characterized in that in its preparation the halogen of halodrine in step 2) is, F, Cl, Br or I; The alcohol formed is a C1-10 alkyl alcohol and the acid anhydride is used as a catalyst.

    [9]
    9. A pharmaceutically active sugar molecule and its method of synthesis, according to claim 7, characterized in that in its preparation form the acid used in step 3) is sodium azide or potassium azide.

    [10]
    10. A pharmaceutically active sugar molecule and its method of synthesis, according to claim 7, characterized in that in its preparation form the compound of the formula (5) is separated by a cation exchange resin in the subsequent treatment to step (4).
    类似技术:
    公开号 | 公开日 | 专利标题
    JP3773153B2|2006-05-10|Sialic acid derivatives
    Huang et al.2006|A novel and efficient ionic liquid supported synthesis of oligosaccharides
    CN108558961B|2019-08-06|Plesiomonas shigelloides O51 serotype O antigen oligosaccharides chemical synthesis process
    Ness et al.1951|The reaction of tribenzoyl-α-L-rhamnopyranosyl bromide with methanol. Various benzoylated derivatives of L-rhamnose
    ES2646628B1|2018-10-05|PHARMACEUTICALLY ACTIVATED SUGAR MOLECULE AND ITS SYNTHESIS METHOD
    Sau et al.2012|Stereoselective glycosylations by nitrosyl tetrafluoroborate-catalyzed activation of glycosyl trichloroacetimidate derivatives
    CN109627270B|2020-12-29|Chemical synthesis method of Pseudomonas aeruginosa O11 serotype O antigen oligosaccharide
    CN108610386B|2020-11-24|Preparation method of substituted benzyl or substituted phenyl beta-D-hexuronic acid glucoside
    CN101671376B|2013-04-17|Alkannin acetyl glucose and preparation method and application thereof
    JP4253858B2|2009-04-15|Fullerene derivative and method for producing the same
    CN103610669B|2018-03-27|Double | class glutathione S transsulfurases are dived inhibitor
    CN102146107A|2011-08-10|Synthesis and anti-tumor activity of |-2-hydroxyalkyl-1,4-dihydroxyl-9-10-anthraquinone and glycosyl conjugates
    JP3163359B2|2001-05-08|Sulfated oligosaccharide compounds
    Chen et al.2006|A concise and practical synthesis of antigenic globotriose, α-d-Gal-|-β-d-Gal-|-β-d-Glc
    JP2005538080A|2005-12-15|Method for synthesizing 2-deoxy-L-ribose
    Anzai et al.1973|Compounds Relating to Dibenzoyladenine Riboside. The Choice between the N 6, 1-Dibenzoyl and N 6, N 6-Dibenzoyl Structures
    CN103435586B|2015-08-12|Containing the polyamine derivative and its preparation method and application of flavones structure
    CN108159040B|2020-06-23|Preparation method and application of xylose carbon glycoside drugs
    McCloskey et al.1943|The Preparation of β-Primeverose Heptaacetate and β-Vicianose Heptaacetate
    US3738979A|1973-06-12|O2,2'-cyclocytidine-3'-phosphate and process for producing same
    Narouz et al.2013|Improved Synthesis of 6-Azido-6-deoxy-and 6, 6′-Diazido-dideoxy-α, α-trehaloses
    CN107011336B|2020-08-14|PH fluorescent probe with pyridine as protonation site and application thereof
    Wolfrom et al.1951|Action of Heat on D-Fructose. II. 1 Structure of Diheterolevulosan II
    Agnihotri et al.2006|Synthesis of a di-and a trisaccharide related to the O-antigen of Escherichia coli O83: K24: H31
    LeMaistre et al.1948|THE REACTION OF SUCROSE WITH ETHYLENE OXIDE1
    同族专利:
    公开号 | 公开日
    CN104788512A|2015-07-22|
    ES2646628R1|2017-12-27|
    ES2646628B1|2018-10-05|
    WO2016145997A1|2016-09-22|
    引用文献:
    公开号 | 申请日 | 公开日 | 申请人 | 专利标题
    CN104788512A|2015-03-13|2015-07-22|淮安市匹克斯生物科技有限公司|Application method of synthesis of medicinal active saccharide molecules in Escherichia coli resistance|CN104788512A|2015-03-13|2015-07-22|淮安市匹克斯生物科技有限公司|Application method of synthesis of medicinal active saccharide molecules in Escherichia coli resistance|
    法律状态:
    2018-10-05| FG2A| Definitive protection|Ref document number: 2646628 Country of ref document: ES Kind code of ref document: B1 Effective date: 20181005 |
    优先权:
    申请号 | 申请日 | 专利标题
    CN201510109400|2015-03-13|
    CN201510109400.0A|CN104788512A|2015-03-13|2015-03-13|Application method of synthesis of medicinal active saccharide molecules in Escherichia coli resistance|
    PCT/CN2016/075585|WO2016145997A1|2015-03-13|2016-03-04|Pharmaceutically active sugar molecule and synthesis method thereof|
    [返回顶部]