JPS6041049B2 - Anti-inflammatory agents containing ortho- or meta-aminobenzoic acid derivatives - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention is based on the following general formula (1) [wherein R is the basic residue of a monosaccharide or trisaccharide (however, among monosaccharides, arabinose, xylose, glucose, galactose, and mannose are excluded) , an amino sugar residue or a dioxy sugar residue (excluding rhamnose), and the R,1NH- group is in the ortho or meta position.

] Ortho- or meta-aminobenzoic acid derivatives or pharmaceutically acceptable salts or alkyl esters thereof (
The present invention relates to an anti-inflammatory agent containing ``this substance'' as an active ingredient.

Conventionally, synthetic compounds and antibiotics have been used as anticancer agents, but although these have excellent painkilling effects, they have the disadvantage of being highly toxic and causing side effects because they also act on normal cells.

Therefore, recently, polysaccharides of various origins have attracted attention because they exhibit anticancer effects by enhancing the immunological ability of the host. The present inventors have already developed and provided to society an anticancer agent made from polysaccharides derived from basidiomycetes, but during research on the structure and activity of this anticancer agent, aminobenzoic acid-N-D-mannoside, aminobenzoic acid-N- L-arabinoside, aminobenzoic acid-N-D-glucoside, aminobenzoic acid-N-D
It has been found that -galactoside and aminobenzoic acid -N-L-rhamnoside have various useful physiological activities. However, these substances are not necessarily sufficient to maintain their medicinal efficacy over a long period of time.

As a result of further research, it was discovered that the compound represented by the above-mentioned single-pronged formula (1), which has low toxicity and high efficiency, is advantageous, and the present invention has been completed. Although this substance has a simple structure, it has extremely low toxicity and has no antibacterial activity, so it can be administered for a long period of time without worrying about disturbing the intestinal flora. Furthermore, it does not have mutagenicity or affect cell-mediated or humoral immunity, and therefore does not pose any risk of teratogenicity or allergic reactions to healthy people, making it an extremely safe drug. In addition, all of these substances have anti-inflammatory effects and are useful as anti-inflammatory agents. Salts of this substance include alkali metal, alkali metal, aluminum salts, etc. As the alkali metal and alkali metal salts, any salt may be used as long as it is acceptable as a drug, and usually Na, K , Mg, Ca, etc. are preferable, and Na is particularly preferable.

Further, as the ester of this substance, methyl, ethyl, propyl, butyl ester, etc. are preferable. R in the above formula (1),
represents a bran residue amino sugar residue or deoxy sugar residue of a monosaccharide or trisaccharide other than arabinose, xylose, glucose, galactose, mannose and rhamnose, and these sugars are D or L form or Q-anomer or 8- It can be in the form of an anomer or a mixture of anomers.

Therefore, the present substance can also be Q or 8 or a mixed anomer thereof. This substance can be produced by the following method. A sugar or aminobenzoic acid or its ester is dissolved in a solvent (e.g. water, alcohol (e.g. methanol, ethanol), acetone, chloroform, dioxane, DMSO) for 2000 to 2000 min in the presence or absence of a catalyst. 200qo, preferably 5
The reaction time is 1 minute to 4 hours, preferably 30 minutes to 24 hours, at 0qo to 150oo. Here, the catalyst is preferably acetic acid or a salt thereof, hydrochloric acid, ammonium chloride, etc., and is added for 0.1 to 5 minutes to the above amount. Ammonium chloride is not necessarily suitable for condensation reactions using disaccharides or ternary brans, but as a result of investigating effective catalysts, we found that acetic acid is particularly effective. In this case, aminobenzoic acid (salts, including lower alkyl esters) 2 to 6 days, solvent 2 to 200
The most favorable results were obtained when the ratio of 1 to 2 parts of acetic acid to that of acetic acid was used.

When the amount of acetic acid used was below this range, the yield decreased, and when it was above this range, no increase in the product was observed. After the reaction, the reaction product is cooled, either as it is or concentrated to precipitate crystals of the reaction product, separated from the furnace, and washed with water, methanol, acetone, ether, etc. Further recrystallization is performed to obtain this substance. A well-known method was used to replace hydrogen in the carboxyl group of this substance with a base. That is, this substance was dissolved in an alcoholic aqueous solvent and an inorganic salt was added for substitution. The physicochemical properties of this substance example obtained by the above manufacturing method are shown in Table 1 below.
Shown below.

Further, infrared absorption spectra are shown in FIGS. 1 to 41. The analysis method in Table 1 is as follows. {1' Melting point Measured using a Yanagimoto melting point measuring device.

(21 Elemental Analysis Measured using Yanagimoto CHN Coder Model MT2.

'31 UV Measurement was performed using a Hitachi EPS-3r self-recording spectrophotometer.

[4} IR KBr by JASCO DS-701G type
It was measured by the method.

In addition, the drawing numbers are sample No. in Table 1. matches.

Table 1 Physical properties of this substance Next, the toxicological properties of this substance are shown.

1. Acute toxicity Acute toxicity by forced oral administration was investigated using ICR-JCL mice.

This substance was dissolved or dissolved in distilled water, and the solution was adjusted to a predetermined amount using a stomach tube and administered. After administration, the symptoms of toxicity were continued to be observed, and the mortality rate was determined to be LD5 based on the mortality rate up to the 7th day. I found the value. The findings were obtained through autopsy in both surviving and dead cases. L
Values by D are Richfield-Wilcoxon (Litc
hfieldWilcoxon) graphic calculation method. The results are shown in Table 2. Both are LD5. The value is large, and it can be said that it is a low toxicity substance and an extremely safe drug. 2 Antibacterial activity Prepare a 2-fold dilution series by dissolving or suspending this substance in distilled water, mix this dilution with 9 times the amount of heated and melted agar medium, and place it in a petri dish. It was poured and made into a flat plate.

Hartinfusion agar (bacteria) and Sabouraud agar (fungi) were used as the culture medium, and the pre-cultured test bacteria were smeared and inoculated. Bacteria: 370, fungi: 25, 0, 3 -
The cells were cultured for 7 days and the presence or absence of growth was examined.

The following bacterial species were used as test bacteria.

Pseudomonas aeruginosa (Pseudomonas aemgn0
SalAM1514) Escherichia coli
coliIFO12734) Yellow Staphylococcus (
Staphylococcus, Bacillus subtilis, Bacillus subtilis, Baker's yeast, Saccharomyces, cerevjs
iae lAM4207) Candida yeast (Candi albjcans ATCC752) White light bacteria (Tri
chophy's n meta and ophy's IF06
124) Black mold (Aspergm ship nl connection rlam30
01) As a result, this substance has a 1/9 effect on all bacteria.
/ secretion showed no growth inhibition.

3 Mutagenicity First, we conducted a study using Rec-assay.

In other words, the cell repair defective strain (Bad11 Satoshis costili
sM45) and a recombinant repair carrier strain (B. s costil; s day 1
7) were mixed with B-0 agar toji (meat extract 10 times, polybeptone 10 times, NaC 15 times, agar 15 times, distilled water 1 hour).
o0', pH 7.0) were streaked so that the starting points did not touch each other. After dissolving or suspending this substance in sterile water and absorbing 0.05' of it into a circular oven paper with a diameter of 8,
Immediately, the mixture was left still so as to cover the starting point of the streak, and cultured overnight to measure the length of the growth inhibition castle. Kanamycin was used as a negative control, and mitomycin C was used as a positive control. The results of the Rec-assay are shown in Table 3.

None of these substances exhibits mutagenicity even when applied at high concentrations, and is known to be a highly safe drug. Table 3
Rec-Assay 4 Delayed intradermal reaction ICR-JC to understand the effect of this substance on cell-mediated immunity
Paw reaction using sheep red blood cells as an antigen using L mice (
Footpad reaction) was performed.

A 10% volume of sheep red blood cells was suspended in physiological saline, and 0.2 of this solution was injected into the tail vein to perform primary sensitization.
After a further 7 days, a 40% volume suspension of sheep erythrocytes 0.05
Noto was injected into foot pigs for secondary sensitization, and the thickness of foot pigs was measured the next day.

This substance was administered intraperitoneally at 250 9/k9 five times on consecutive days, mainly on the day of primary sensitization. As a result, no significant difference was observed in the increase in foot thickness in the group administered with this substance compared to the control (non-administered) group.

5 Antibody production ability In order to understand the effect of this substance on humoral immunity, ICR-J
CL mice were given 0.0% suspension of sheep red blood cells.
2 was injected into the tail vein for sensitization, and 7 days after sensitization, blood was collected and antibody production ability was measured by hemagglutination reaction.

The substance was intraperitoneally administered at 250 pm/k9 five times on consecutive days, mainly on the day of sensitization. As a result, no significant difference was observed in the agglutination value between the group administered with this substance and the control group.

Next, we will discuss the pharmacological properties of this substance, namely its anti-inflammatory effects.

(1) Carrageenin edema inhibitory effect This substance was dissolved or suspended in distilled water in 6-week-old Donryu female rats (purchased from Tokyo Experimental Animals ■), 10 in each group, according to the method of VanVrmanet.al. (1963). 10
9/k9 of 00 was orally administered by force, and 1 hour after administration, 0.1% of 1% Cana sella enin saline suspension was injected into the bran of the right hind paw, and the paw volume was measured over time and suppressed using the following formula. The rate was calculated.

(1-T/C)×100=1. R. (%) T: Administration group average bonito volume C: Control group {2) Granuloma suppression effect Win to ret. al. (1963), 1
Groups of 6 6-week-old Donryu female rats (sold from Tokyo Experimental Animals) were subcutaneously placed on the backs of 30 ± 1 m9 with the midline symmetrical.
The substance containing two cotton wool pellets was orally administered for 7 days continuously, and on the 8th day, the granulation was removed, the dry weight was measured, and the inhibition rate was determined in the same manner as in m above.

'3} Anti-destruction effect Mari riset. al. (1965) et al., 1
A pouch was created under the skin of the back of a group of 6 6-week-old Donryu female rats (purchased from Tokyo Experimental Animals ■), and 0.5 ml of 1% Crotonoil (in sesame oil) was injected into the pouch. The substance was continuously administered for 5 days, and on the 6th day, the amount of exudate in the pouch was measured and the inhibition rate was determined in the same manner as in {1} above.

The results are shown in Table 4.

The above results indicate that this substance has anti-inflammatory effects.

Table 4 Anti-inflammatory effect of this substance Dosage 1000 items p. o. (Control Group 20) This substance has low acute toxicity and few other side effects, so it is useful as a medical treatment for both animals and humans.

As a medicine, it is used for human use as an anti-inflammatory agent. Next, we will discuss the formulation of this substance. When used as an anti-inflammatory agent, the substance can be used in any convenient form to obtain a medicinal effect depending on the type and symptoms of the disease, and can be used alone or in mixtures with pharmaceutically acceptable diluents and other drugs. Can be used.

The substances can be provided in dosage unit form.

It contains an effective amount of the active ingredient, and its forms include powders, granules, tablets, bran-coated tablets, capsules, etc. for oral use.
syrups, pills, suspensions, solutions, emulsions, etc.
For parenteral use, it can be in the form of an ampoule or bottle as an injection solution. Suppositories are also available. The diluent may be solid, liquid, or semi-solid, and examples include the following. i.e. excipients, fillers, binders, wetting agents, disintegrants,
surfactants, lubricants, dispersants, buffers, fragrances, preservatives,
These include solubilizing agents, solvents, etc. Specific examples include lactose, sucrose, sorbitol, mannitol, starch,
Precipitated calcium carbonate, heavy magnesium oxide, talc, calcium stearate, magnesium stearate, cellulose or its derivatives, amylobectin, polyvinyl alcohol, seratin, surfactant, water, raw saline, ethanol, glycerin, propylene glycol,
These include cacao butter, lauric fat, petrolatum, paraffin, and higher alcohols.

The bio-embedded activator of the present invention can be produced by any known method. The active ingredient in the compositions used in this invention generally ranges from 0.01% to 10%. % preferably 0.05%
From 80Wt. %included. The bioactive agent of the present invention can be administered orally or parenterally to humans and animals, but oral administration is preferred.

Oral administration includes sublingual administration. Parenteral administration includes injection administration (eg, subcutaneous, intramuscular, intravenous injection, infusion), rectal administration, and the like. The dose of the bioactive agent of the present invention depends on whether it is an animal or a human, and is influenced by age, individual differences, medical conditions, etc., and in some cases, doses outside the ranges below may be administered, but in general, it is intended for humans. In case of body weight lk9, the oral dosage of the substance is 0.1 to 500 females per day, preferably 1 to 250 9, and the parenteral dosage is also 0.01 to 9.
9 of 200, preferably 0.1 to 9 of 100, once to 4
Administer in divided doses. Hereinafter, the present invention will be explained in more detail by showing formulation examples and manufacturing examples of the substance of the present invention.

Parts in the examples below indicate weight. Formulation Example 1 is uniformly mixed to form a powder or fine granules with a size of 350 μm or less.

Further, this powder was put into a capsule container to form a capsule. Formulation Example 2 is uniformly mixed, crushed, granulated, dried, and then divided into jaw granules having a size of 1410 mm to 177 mm.

Formulation Example 3 In place of o-aminobenzoic acid ethyl-N-cellobioside in Example 2, m-aminobenzoic acid ethyl ester-N
- Make forehead granules in the same manner using L-fucoside,
4 parts of Stear IJ calcium phosphate were added to 96 parts of this jaw granule and compression molded to form tablets with a diameter of 10 pieces.

Formulation Example 4 1 part of microcrystalline cellulose and 3 parts of calcium stearate were added to 9 parts of the grains obtained by the method of Example 2, and compression molded to form tablets with a diameter of 8 sides. Add a suspension of mixed calcium carbonate to form bran-coated tablets.

Formulation Example 5 is heated and mixed, then put into an ampoule and sterilized to prepare an injection.

Formulation Example 6 Sodium o-aminobenzoate-N-N- in Example 5
An injection is prepared in the same manner using o-aminobenzoic acid-N-maltoside in place of acetyl-D-glucosaminide.

Production Example 1 Production method of o-aminobenzoic acid-N-D-riboside-Na salt o-aminobenzoic acid 2.7, D-ribose 3.0
In the evening, 0.3 μm of ammonium chloride was added to 30% 94% ethyl alcohol and heated under reflux for condensation.

If the reaction solution is left in the refrigerator, crystals will precipitate. The reaction solution is filtered, the crystals are washed with ether, and recrystallized several times from methyl alcohol to obtain colorless needle-like crystals. The yield was 5.5%.

Thus obtained o-aminobenzoic acid-N-D
- Gradually dissolve the liposide in a 1% aqueous solution containing the calculated amount of NaOH, filter out the insoluble matter, concentrate the filtrate under reduced pressure, add a large excess of acetone, dehydrate, and dry to obtain colorless crystals. Ta.

The yield was 100%, and the total yield was 5.5%.

Production Example 2 Production method of o-aminobenzoic acid-N-2-deoxy-D-liposside-Na salt o-aminobenzoic acid 2.7 hours, 2-deoxy-D-ribose 2.5 hours, ammonium chloride 0
．． 25 and 30 pieces were added to 94% ethyl alcohol and heated under reflux for condensation.

If the reaction solution is left in the refrigerator, crystals will precipitate. The reaction solution is filtered, the crystals are washed with ether, and recrystallized several times from 50% methyl alcohol to obtain colorless needle-like crystals. The yield was 0.4%.

Thus obtained, o-ami/benzoic acid-N-2
-Deoxy-D-liposide was gradually dissolved in a 1% aqueous solution containing the calculated amount of NaOH, the insoluble matter was filtered, the o liquid was concentrated under reduced pressure, a large excess of acetone was added, and after dehydration, colorless crystals were formed when dried. can get.

The yield was 100%, and the total yield was 4.0%.

Production Example 3 Production method of o-aminobenzoic acid-N-D-fructoside-Na salt O-aminobenzoic acid 2.7 hours, D-fructose 3.6 hours, ammonium chloride 0.3 hours were added in 30'94.
% ethyl alcohol and heat condensation under reflux.

If the reaction solution is left in the refrigerator, crystals will precipitate. The reaction solution is filtered, the crystals are washed with ether, and recrystallized several times from 50% methyl alcohol to obtain colorless needle-like crystals. The yield was 4.5%.

Thus obtained o-aminobenzoic acid-N-D
- Gradually dissolve the fructosides in a 1% aqueous solution containing a calculated amount of NaOH, filter the insoluble materials, and concentrate the filtrate under reduced pressure.
Add a large excess of acetone, dehydrate, and then dry to obtain colorless crystals.

The yield was 100%, and the total yield was 4.5%.

Production Example 4 Production method of o-aminobenzoic acid-N-L-sorboside Na salt o-aminobenzoic acid 2.7 hours, L-sorbose 3
．． After 6 days, 30 minutes of ammonium chloride was added to 94% ethyl alcohol, and the mixture was heated and condensed under reflux.

If the reaction solution is left in the refrigerator, crystals will precipitate. The reaction solution is filtered, the crystals are washed with ether, and the crystals are re-crystallized several times from methyl alcohol to obtain needle-like crystals with a poor color. The yield was 3.7%.

Thus obtained, o-aminobenzoic acid-N-L
- Gradually dissolve sorbotucide in a 1% aqueous solution containing a calculated amount of NaOH, remove insoluble matter, concentrate the filtrate under reduced pressure, add a large excess of acetone, dehydrate, and dry to obtain colorless crystals. .

The yield was 100%, and the total yield was 3.7%.

Production Example 5 Production method of o-aminobenzoic acid-N-L-fucoside-Na salt o-aminobenzoic acid 1.2 hours, L-fucose 1.4 hours
In the evening, 0.2 tons of ammonium chloride was added to 15' of 94% ethyl alcohol, and the mixture was heated and condensed under reflux.

If the reaction solution is left in the refrigerator, crystals will precipitate. The reaction solution is filtered, the crystals are washed with ether, and recrystallized several times from 50% methyl alcohol to obtain colorless needle-like crystals. The yield was 40.2%.

Thus obtained o-aminobenzoic acid-N-L
- Gradually dissolve the fucoside in a 1% aqueous solution containing the calculated amount of NaOH, filter the insoluble matter, concentrate the filtrate under reduced pressure, add a large excess of acetone, dehydrate, and dry to obtain colorless crystals. .

The yield was 100%, and the total yield was 40.2%.

Production Example 6 Production method of o-aminobenzoic acid-N-D-glucuronolactonide-Na salt o-aminobenzoic acid 2.5 hours, D-glucuronolactone 3.2 hours, ammonium chloride 0.3 hours 25 hours The mixture was added to 94% ethyl alcohol and heated under reflux for condensation.

If the reaction solution is left in the refrigerator, crystals will precipitate. The reaction solution is filtered, the crystals are washed with ether, and recrystallized several times from methyl alcohol to obtain colorless needle-like crystals. The yield was 25.2%.

Thus obtained o-aminobenzoic acid-N-○
- 1% glucuronolactonide with calculated amount of NaOH
Gradually dissolve in an aqueous solution, remove insoluble matter, concentrate the filtrate under reduced pressure, add a large excess of acetone, dehydrate, and then dry to obtain colorless crystals.

The yield was 100%, and the total yield was 25.2%.

Production Example 7 Production method of aminobenzoic acid-N-methyl-D-glucuronide-Na salt o-Aminobenzoic acid 2.0 hours, methyl-D-glucuronic acid 3.0 hours, ammonium chloride 0.4 hours 10% on paper 94% Add to ethyl alcohol and heat condensate under reflux.

If the reaction solution is left in the refrigerator, crystals will precipitate. The reaction solution is filtered, the crystals are washed with ether, and recrystallized several times from 50% methyl alcohol to obtain colorless needle-like crystals. The yield was 12.0%.

The thus obtained o-aminobenzoic acid-N-methyl-D-glucuronide was dissolved in 1% containing a calculated amount of NaOH.
Gradually dissolve in an aqueous solution, filter insoluble matter, concentrate the filtrate under reduced pressure, add a large excess of acetone, dehydrate, and dry to obtain colorless crystals.

The yield was 100%, and the total yield was 12.0%.

Production example 8o-aminobenzoic acid-N-N-acetyl D
-Production method of glucosaminide-Na salt o-aminobenzoic acid 1.9 times, N-acetyl-D-glucosamine 3.0 times,
0.05 ml of ammonium chloride was added to 150% ethyl alcohol and heated under reflux for condensation.

If the reaction solution is left in the refrigerator, crystals will precipitate. The reaction solution is filtered, the crystals are washed with ether, and recrystallized several times from 50% methyl alcohol to obtain colorless needle-like crystals. The yield was 9.1%.

Thus obtained o-aminobenzoic acid-N-N
-Acetyl-D-glucosaminide was gradually dissolved in a 1% aqueous solution containing the calculated amount of NaOH, the insoluble matter was filtered, the filtrate was concentrated under reduced pressure, a large excess of acetone was added, and after dehydration, colorless crystals were obtained by drying. can get.

The yield was 100%, and the total yield was 9.1%.

Production Example 9 Production method of o-aminobenzoic acid-N-maltoside-Na salt o-aminobenzoic acid 1.4 hours, maltose 3.6 hours,
Add 1.4 parts of glacial acetic acid, 2 parts of water, and 5 parts of EtOH, and heat to condense under reflux.

If the reaction solution is left in the refrigerator, crystals will precipitate. The reaction solution is filtered, the crystals are washed with ether, and recrystallized several times from 50% methyl alcohol to obtain colorless needle-like crystals. The yield was 15.2%. The thus obtained o-aminobenzoic acid-N-maltoside was gradually dissolved in a 1% aqueous solution containing a calculated amount of NaOH, the insoluble matter was filtered, the filtrate was concentrated under reduced pressure, and a large excess of acetone was added. Add
After dehydration and drying, colorless crystals are obtained. Yield 100
%, and the total yield was 15.2%.

Production example 10 O-aminobenzoic acid/N-cellobioside-Na salt production method O-aminobenzoic acid 1.4 hours, cellobiose 3.4 hours, glacial acetic acid 1.4 hours, water 13' to 5' Add ethyl alcohol and heat to condense under reflux.

If the reaction solution is left in the refrigerator, crystals will precipitate. The reaction solution is filtered, the crystals are washed with ether, and recrystallized several times from 50% methyl alcohol to obtain colorless needle-like crystals. The yield was 13.0%.

The thus obtained o-aminobenzoic acid-N cellobioside was gradually dissolved in a 1% aqueous solution containing a calculated amount of NaOH, the impurities were removed, the filtrate was concentrated under reduced pressure, and a large excess of acetone was added. is added, dehydrated, and dried to obtain colorless crystals.

The yield was 100%, and the total yield was 13.0%.

Production Example 11 Production method of o-aminobenzoic acid-N-saccharosidium Na salt O-aminobenzoic acid 1.4 hours, saccharose 3.6 hours, water 5', acetic acid 1.4' of ethyl alcohol and heat condensation under reflux.

If the reaction solution is left in the refrigerator, crystals will precipitate. The reaction solution is filtered, the crystals are washed with ether, and recrystallized several times from 50% methyl alcohol to obtain colorless needle-like crystals. The yield was 1.2%.

The thus obtained o-aminobenzoic acid-N-saccharoside was gradually dissolved in a 1% aqueous solution containing a calculated amount of NaOH, filtered to remove impurities, and the filtrate was concentrated under reduced pressure. Add acetone, dehydrate, and dry to obtain colorless crystals.

The yield was 100%, and the total yield was 1.2%.

Production Example 12 Production method of o-aminobenzoic acid-N-lactosid-Na salt o-aminobenzoic acid 1.4 hours, lactose 3.6 hours,
Add 10 parts of water and 1.4 parts of glacial acetic acid to 4.2 parts of ethyl alcohol and heat to condense under reflux.

If the reaction solution is left in the refrigerator, crystals will precipitate. The reaction solution is filtered, the crystals are washed with ether, and recrystallized from ethyl alcohol several times to obtain colorless needle-like crystals. The yield was 15.2%.

The thus obtained o-aminobenzoic acid-N-lactoside was gradually dissolved in a 1% aqueous solution containing a calculated amount of NaOH, the insoluble matter was filtered, and the filtrate was concentrated under reduced pressure. Add acetone, dehydrate, and dry to obtain colorless crystals.

The yield was 100%, and the total yield was 15.2%.

Production example 13Production method of aminobenzoic acid-N-maltotriosid-Na salt o-aminobenzoic acid 1.4 hours, maltotriose 5.0 hours, water 2.8 hours, acetic acid 1.4 hours, 8.5 hours. The mixture is added to ethyl alcohol and heated under reflux for condensation.

If the reaction solution is left in the refrigerator, crystals will precipitate. By pouring the reaction solution, washing the crystals with ether, and repeating the crystallization several times from ethyl alcohol, colorless needle-like crystals are obtained. The yield was 9.6%.

The thus obtained o-aminobenzoic acid-N-maltotrioside was gradually dissolved in a 1% aqueous solution containing a calculated amount of NaOH, the insoluble materials were removed, the filtrate was concentrated under reduced pressure, and a large excess was removed. Add acetone, dehydrate, and dry to obtain colorless crystals.

The yield was 100%, and the total yield was 9.6%.

Production Example 14 Production of o-aminobenzoic acid methyl ester-N-D-riboside - 3.0 ml of aminobenzoic acid methyl ester, 3.0 ml of 0-ribose, and 0.3 ml of ammonium chloride in 30 [94% ethyl alcohol] Add the mixture and heat to condense under reflux.

If the reaction solution is left in the refrigerator, crystals will precipitate. The reaction solution is filtered, the crystals are washed with ether, and recrystallized several times from ethyl alcohol to obtain colorless needle-like crystals. The yield was 45.9%.

Production Example 15 O-aminobenzoic acid methyl ester - Production method of N-L-fucoside o-aminobenzoic acid methyl ester 1.2 days,
L-fucose 1.3 times, ammonium chloride 0.2 times 1
5' in 94% ethyl alcohol and heat condensed under reflux.

do. If the reaction solution is left in the refrigerator, crystals will precipitate. The reaction solution was filtered, the crystals were washed with ether, and recrystallized several times from 50% methyl alcohol to obtain colorless needle-like crystals. The yield was 21.3%.

Production Example 16 O-aminobenzoic acid methylester N-Nacetyl-D-glucosaminide production method o-aminobenzoic acid methylester 2.0, N-acetyl-D-glucosamine 3
．． At 0 pm, 0.5 oz of ammonium chloride was added to 150 ml of ethyl alcohol and heated under reflux for condensation.

If the reaction solution is left in the refrigerator, crystals will precipitate. The reaction solution is filtered, the crystals are washed with ether, and recrystallized several times from 50% ethyl alcohol to obtain colorless needle-like crystals. The yield was 2.1%.

Production Example 17 Production method of o-aminobenzoic acid methyl ester-N-maltoside o-aminobenzoic acid methyl ester 1.5 hours,
After 3.6 hours of maltose, 1.5 hours of water and 1.5 hours of glacial acetic acid were added to the ethyl alcohol in Step 5, and the mixture was heated and condensed under reflux.

If the reaction solution is left in the refrigerator, crystals will precipitate. The reaction solution is filtered, the crystals are washed with ether, and recrystallized several times from 94% ethyl alcohol to obtain colorless needle-like crystals. The yield was 18.9%.

Production Example 18 Production method of o-aminobenzoic acid methyl ester-N-cellobiosside o-aminobenzoic acid methyl ester 1.5#
, 3.4 parts of cellbiose, 13 parts of water and 1.4 parts of acetic acid were added to 5 parts of ethyl alcohol, and the mixture was heated and condensed under reflux.

If the reaction solution is left in the refrigerator, crystals will precipitate. The reaction solution is filtered, the crystals are washed with ether, and recrystallized several times from ethyl alcohol to obtain colorless needle-like crystals. The yield was 6.3%.

Production Example 19 Production method of o-aminobenzoic acid methyl ester-N-lactosid o-aminobenzoic acid methyl ester 1.5 minutes,
Add 3.6 hours of lactose, 1 hour of water, and 1.4 hours of acetic acid to 4.2' of ethyl alcohol, and heat and condense under reflux.

If the reaction solution is left in the refrigerator, crystals will precipitate. The reaction solution is filtered, the crystals are washed with ether, and recrystallized several times from 50% methyl alcohol to obtain colorless needle-like crystals. The yield was 10.5%.

Production Example 20 Production of o-aminobenzoic acid methyl ester-N-maltotrioside o-amino/benzoic acid methyl ester 1.
Moth, maltotriose 5.0%, water 2.8%, acetic acid 1%
．． Add the 4 sides to 4.2' ethyl alcohol under reflux,
Heat condensation.

If the reaction solution is left in the refrigerator, crystals will precipitate. The reaction solution is filtered, the crystals are washed with ether, and recrystallized several times from 50% methyl alcohol to obtain colorless needle-like crystals. The yield was 4.7%.

Production Example 21 Production of methyl aminobenzoate N-D-riboside Add 2.8 hours of ethyl aminobenzoate, 2.5 hours of D-ribose, and 0.25 hours of ammonium chloride to 30% 94% ethyl alcohol. Heat condensation under reflux.

If the reaction solution is left in the refrigerator, crystals will precipitate. The reaction solution is filtered, the crystals are washed with ether, and recrystallized several times from 50% methyl alcohol to obtain colorless needle-like crystals. The yield was 28.2%.

Production Example 22 o-Aminobenzoic acid ethyl ester NL-Production method of L fucoside o-aminobenzoic acid ethyl ester 1.32,
L-fucose 1.3 times, ammonium chloride 0.2 times 1
The mixture was added to 94% ethyl alcohol and heated under reflux for condensation.

If the reaction solution is left in the refrigerator, crystals will precipitate. The reaction solution is filtered, the crystals are washed with ether, and recrystallized several times from 50% methyl alcohol to obtain colorless needle-like crystals. The yield was 28.5%.

Production Example 23 Production of o-aminobenzoic acid methyl ester-N-cellobioside O-aminobenzoic acid ethyl ester 1.7 ml, cellobiose 3.4 ml, water 13 ml, glacial acetic acid 1.4 ml in 11 ml ethyl alcohol. Add the mixture and heat to condense under reflux.

If the reaction solution is left in the refrigerator, crystals will precipitate. The reaction solution is filtered, the crystals are washed with ether, and recrystallized several times from 50% methyl alcohol to obtain colorless needle-like crystals. The yield was 12.3%. Production Example 24 Production method of o-aminobenzoic acid propyl ester-N-D-riboside o-aminobenzoic acid propyl ester 3.
0, D-ribose 3.0, ammonium chloride 0.3
The mixture was added to 300'94% ethyl alcohol and heated under reflux for condensation.

If the reaction solution is left in the refrigerator, crystals will precipitate. The reaction solution is filtered, the crystals are washed with ether, and recrystallized several times from ethyl alcohol to obtain colorless needle-like crystals. The yield was 6.5%.

Production Example 25 Production method of o-aminobenzoic acid propyl ester-N-L-fucoside o-aminobenzoic acid propyl ester 3.
0 evening, L-fucose 3.0 evening, ammonium chloride 0.2
The mixture was added to 20% and 94% ethyl alcohol under reflux.
Heat condensation.

If the reaction solution is left in the refrigerator, crystals will precipitate. The reaction solution is filtered, the crystals are washed with ether, and recrystallized several times from ethyl alcohol to obtain colorless needle-like crystals. The yield was 4.7%.

Production Example 26 Production of o-aminobenzoic acid propyl ester-N-cellobioside o-aminobenzoic acid propyl ester 2.
02, cellobiose 3.4 minutes, water 13', acetic acid 1.4
Add '' to ethyl alcohol of '11' and heat condensation under reflux.

If the reaction solution is left in the refrigerator, crystals will precipitate. The reaction solution is filtered, the crystals are washed with ether, and recrystallized several times from 94% ethyl alcohol to obtain colorless needle-like crystals. The yield was 5.5%.

Production Example 27 Production of o-aminobenzoic acid butyl ester - N-D-ribotsuside 3.8% o-aminobenzoic acid butyl ester, 3.0% D-ribose, 0.3% ammonium chloride and 94% ethyl alcohol and heat condensation under reflux.

If the reaction solution is left in the refrigerator, crystals will precipitate. The reaction solution is filtered, the crystals are washed with ether, and re-crystallized several times from 94% ethyl alcohol to obtain cool-colored needle-shaped crystals. The yield was 21.5%.

Production Example 28 O-Aminobenzoic acid butyl ester - Production method of N-L-fucoside o-Aminobenzoic acid butyl ester 1.5 minutes,
L-fucose 1.3 times, ammonium chloride 0.2 times 1
5' in 94% ethyl alcohol and heat condensation under reflux.

If the reaction solution is left in the refrigerator, crystals will precipitate. The reaction solution is filtered, the crystals are washed with ether, and recrystallized several times from 50% methyl alcohol to obtain colorless needle-like crystals. The yield was 33.6%.

Production Example 29 Production method of aminobenzoic acid butyl ester-N-cellobioside o-aminobenzoic acid butyl ester 1.9 parts, cellobiose 3.4 parts, water 13', acetic acid 1.4'
was added to ethyl alcohol and heated under reflux for condensation.

If the reaction solution is left in the refrigerator, crystals will precipitate. The reaction solution was poured into a filtrate, the crystals were washed with ether, and the crystals were reheated several times using 94% ethyl alcohol to obtain colorless needle-like crystals. The yield was 3.9%.

Production Example 30 Production method of m-aminobenzoic acid-N-○-riboside Na salt m-aminobenzoic acid 2.7 m, D-ribose 3.0
In the evening, 0.3 μm of ammonium chloride was added to 30% 94% ethyl alcohol and heated under reflux for condensation.

If the reaction solution is left in the refrigerator, crystals will precipitate. The reaction solution is filtered, the crystals are washed with ether, and recrystallized several times from methyl alcohol to obtain colorless needle-like crystals. The yield was 3.0%.

Thus obtained m-aminobenzoic acid-N-D
- Gradually dissolve the liposide in a 1% aqueous solution containing the calculated amount of NaOH, filter out the undissolved matter, concentrate the filtrate under reduced pressure, add a large excess of acetone, dehydrate, and dry to obtain colorless crystals. It will be done.

The yield was 100%, and the total yield was 3.0%.

Production Example 31 Production method of m-aminobenzoic acid-N-2-deoxy-○-riboside-Na salt m-aminobenzoic acid 2.7 days, 2-
Deoxy-D-ribose 2.5 hours, ammonium chloride 0
．． The mixture was added to 30% 94% ethyl alcohol and heated under reflux.

If the reaction solution is left in the refrigerator, crystals will precipitate. The reaction solution is filtered, the crystals are washed with ether, and recrystallized several times from ethyl alcohol to obtain colorless needle-like crystals. The yield was 3.2%.

Thus obtained m-ami/benzoic acid-N-2
-Deoxy-○-riboside was gradually dissolved in a 1% aqueous solution containing the calculated amount of NaOH, the insoluble matter was filtered off, the filtrate was concentrated under reduced pressure, a large excess of acetone was added, and after dehydration, colorless crystals were obtained when dried. can get.

The yield was 100%, and the total yield was 3.2%.

Production Example 32 Production method of m-aminobenzoic acid-N-D-fructoside Na salt o-aminobenzoic acid 2.7 hours, D-fructose 3.6 hours, ammonium chloride 0.3 hours in 30'94
% ethyl alcohol and heat condensation under reflux.

If the reaction solution is left in the refrigerator, crystals will precipitate. The reaction solution is filtered, the crystals are washed with ether, and recrystallized several times from methyl alcohol to obtain colorless needle-like crystals. The yield was 2.2%.

Thus obtained m-aminobenzoic acid-N-D
- Gradually dissolve the fructoside in a 1% aqueous solution containing a calculated amount of NaOH, filter the insoluble matter, and concentrate the filtrate under reduced pressure.
Add a large excess of acetone, dehydrate, and then dry to obtain colorless crystals.

The yield was 100%, and the total yield was 2.2%.

Production example 33 Production method of m-aminobenzoic acid-N-L-sorbose sodium salt m-aminobenzoic acid 2.7 m, L-sorbose 3
．． After 6 days, 0.3 days of ammonium chloride was added to 30M 94% ethyl alcohol and heated under reflux for condensation.

If the reaction solution is left in the refrigerator, crystals will precipitate. The reaction solution is filtered, the crystals are washed with ether, and recrystallized several times from methyl alcohol to obtain colorless needle-like crystals. The yield was 1.8%.

The thus obtained m-aminobenzoic acid-N-L
- Gradually dissolve sorbociside in a 1% aqueous solution containing a calculated amount of NaOH, filter out insoluble materials, and concentrate the filtrate under reduced pressure.
Add a large excess of acetone, dehydrate, and then dry to obtain colorless crystals.

The yield was 100%, and the total yield was 1.8%.

Production Example 34 Production method of m-aminobenzoic acid-N-L-fucoside-Na salt m-aminobenzoic acid 1.2 hours, L-fucose 1.4 hours
In the evening, 2.0 g of ammonium chloride was added to ethyl alcohol and heated under reflux for condensation.

If the reaction solution is left in the refrigerator, crystals will precipitate. The reaction solution is filtered, the crystals are washed with ether, and recrystallized several times from 50% methyl alcohol to obtain colorless needle-like crystals. The yield was 12.0%.

Thus obtained m-ami/benzoic acid-N-L
-Fucoside is gradually dissolved in a 1% aqueous solution containing a calculated amount of NaOH, unmelted substances are removed, the filtrate is concentrated under reduced pressure, a large excess of acetone is added, and after dehydration, colorless crystals are obtained.

The yield was 100%, and the total yield was 12.0%.

Production Example 35Production method of m-aminobenzoic acid-N1D-glucuronolactonide-Na salt m-aminobenzoic acid 2.5
In the evening, 3.2 hours of D-glochronolactone and 0.3 hours of ammonium chloride were added to 25M 94% ethyl alcohol, and the mixture was heated and condensed under reflux.

If the reaction solution is left in the refrigerator, crystals will precipitate. The reaction solution is filtered, the crystals are washed with ether, and recrystallized several times from methyl alcohol to obtain colorless needle-like crystals. The yield was 7.0%.

The thus obtained m-aminobenzoic acid-N-○
1% glucuronolactonide with calculated amount of NaOH
Gradually dissolve in an aqueous solution, remove insoluble matter, concentrate the filtrate under reduced pressure, add a large amount of acetone, dehydrate, and dry to obtain colorless crystals.

The yield was 100%, and the total yield was 7.0%.

Production Example 36 Method for producing m-aminobenzoic acid-N-methyl-D-glucuronide Na salt m-amino/benzoic acid 1.0 m, methyl-
1.5 parts of D-glucuronic acid and 0.2 parts of ammonium chloride were added to 10 parts of 94% ethyl alcohol and dissociated by heating under reflux.

If the reaction solution is left in the refrigerator, crystals will precipitate. The reaction solution is filtered, the crystals are washed with ether, and recrystallized several times from 50% methyl alcohol to obtain colorless needle-like crystals. The yield was 8.2%.

The thus obtained m-aminobenzoic acid-N-methyl-D-glucuronide was added to a 1% solution containing a calculated amount of NaOH.
Gradually dissolve in an aqueous solution, remove insoluble matter, concentrate the filtrate under reduced pressure, add a large excess of acetone, dehydrate, and dry to obtain colorless crystals.

The yield was 100%, and the total yield was 8.2%.

Production Example 37 Method for producing m-aminobenzoic acid-N-N-acetyl-D-glucosaminide-Na salt m-aminobenzoic acid 1.9 hours,
3.0 ml of N-acetyl-D-glucosamine and 0.05 ml of ammonium chloride were added to 150 ml of ethyl alcohol and heated under reflux for condensation.

If the reaction solution is left in the refrigerator, crystals will precipitate. The reaction solution is filtered, the crystals are washed with ether, and recrystallized several times from 50% methyl alcohol to obtain colorless needle-like crystals. The yield was 34.9%.

The thus obtained m-aminobenzoic acid-N-N
- Gradually dissolve acetyl-D-glucosamide in a 1% aqueous solution containing the calculated amount of NaOH, remove the impurities, concentrate the filtrate under reduced pressure, add a large excess of acetone, dehydrate, and dry to form colorless crystals. is obtained.

The yield was 100%, and the total yield was 34.9%.

Production Example 38 Method for producing m-aminobenzoic acid-N-maltoside Na salt Add 1.4 parts of m-aminobenzoic acid, 3.6 parts of maltose, and 1.4 parts of glacial acetic acid to ethyl alcohol of 15 and heat under reflux. Condense.

If the reaction solution is left in the refrigerator, crystals will precipitate. By pouring the reaction solution, washing the crystals with ether, and repeating the crystallization several times from methyl alcohol, colorless needle-shaped crystals are obtained. The yield was 45.6%. Obtained in this way,
m-aminobenzoic acid-N-maltoside with calculated amount of Na
Gradually dissolve in a 1% aqueous solution containing OH, filter insoluble matter, concentrate the filtrate under reduced pressure, add a large excess of acetone, dehydrate, and dry to obtain colorless crystals.

The yield was 100%, and the total yield was 456%.

Production Example 39 Production method of m-aminobenzoic acid-N-cellopioside-Na salt m-aminobenzoic acid 1.4 hours, cellobiose 3.4 hours
In the evening, 13 parts of water and 1.4 parts of glacial acetic acid were added to 5 parts of ethyl alcohol, and the mixture was heated and condensed under reflux.

If the reaction solution is left in the refrigerator, crystals will precipitate. The reaction solution is filtered, the crystals are washed with ether, and recrystallized several times from 20% ethyl alcohol to obtain colorless needle-shaped crystals. The yield was 23.9%.

The thus obtained m-aminobenzoic acid-N-cellobioside was gradually added to a 1% aqueous solution containing a calculated amount of NaOH, the insoluble matter was filtered off, and the filtrate was concentrated under reduced pressure to obtain a large excess. Add acetone, dehydrate, and dry to obtain colorless crystals.

The yield was 100%, and the total yield was 23.9%.

Production example 40m-aminobenzoic acid-N-saccharoside-
Method for producing Na salt: 1.4 volumes of aminobenzoic acid, 3.6 volumes of saccharose, 7 volumes of water, and 1.4 volumes of acetic acid are added to 7 volumes of ethyl alcohol and heated under reflux for condensation.

If the reaction solution is left in the refrigerator, crystals will precipitate. The reaction solution is filtered, the crystals are washed with ether, and recrystallized several times from ethyl alcohol to obtain colorless needle-like crystals. The yield was 0.8%.

The thus obtained m-aminobenzoic acid-N-saccharoside was gradually dissolved in a 1% aqueous solution containing a calculated amount of NaOH, filtered to remove impurities, and the filtrate was concentrated under reduced pressure. Add acetone, dehydrate, and dry to obtain colorless crystals.

The yield was 100%, and the total yield was 0.8%.

Production Example 41 Production method of m-aminobenzoic acid-N-lactoside-Na salt m-aminobenzoic acid 1.4 hours, lactose 3.6 hours,
Add 10 parts of water and 1.4 parts of glacial acetic acid to 4.2 parts of ethyl alcohol and heat to condense under reflux.

If the reaction solution is left in the refrigerator, crystals will precipitate. By pouring the reaction solution, washing the crystals with ether, and repeating the crystallization several times from methyl alcohol, colorless needle-shaped crystals are obtained. The yield was 21.7%.

The thus obtained m-aminobenzoic acid-N-lactoside was gradually dissolved in a 1% aqueous solution containing a calculated amount of NaOH, the insoluble materials were removed, the filtrate was concentrated under reduced pressure, and a large excess of acetone was removed. In addition, after dehydration, colorless crystals are obtained by drying.

The yield was 100%, and the total yield was 21.7%.

Production Example 42M-Aminobenzoic acid-N-maltotriosidium Na salt production method - 1.4 parts of aminobenzoic acid, 5.0 parts of maltotriose, 2.8 parts of water, 1.4 parts of glacial acetic acid. 8.5 Add to ethyl alcohol and heat condensate under reflux.

If the reaction solution is left in the refrigerator, crystals will precipitate. The reaction solution is filtered, the crystals are washed with ether, and recrystallized several times from methyl alcohol to obtain colorless needle-like crystals. The yield was 80.3%.

The thus obtained m-aminobenzoic acid-N-maltotrioside was gradually dissolved in a 1% aqueous solution containing a calculated amount of NaOH, the insoluble materials were removed, the filtrate was concentrated under reduced pressure, and a large excess was removed. Add acetone, dehydrate, and dry to obtain colorless crystals.

The yield was 100%, and the total yield was 80.3%.

Production example 43m-aminobenzoic acid methyl ester N-
Production method of L-fucoside 1.2 hours of m-amino/benzoic acid methyl ester, 1.3 hours of L-fuss and 0.2 hours of ammonium chloride were added to 20 tons of 94% ethyl alcohol and heated under reflux for condensation.

If the reaction solution is left in the refrigerator, crystals will precipitate. The reaction solution is filtered, the crystals are washed with ether, and recrystallized several times from 50% methyl alcohol to obtain colorless needle-like crystals. The yield was 15.0%.

Production Example 44 Method for producing m-aminobenzoic acid ethyl ester-N-L-fucoside m-aminobenzoic acid methyl ester 1.3 days,
L-fucose 3.0 times, ammonium chloride 0.2 times 1
5. Add to 94% ethyl alcohol on the table and heat condensate under reflux.

If the reaction solution is left in the refrigerator, crystals will precipitate. The reaction solution is filtered, the crystals are washed with ether, and the reaction is repeated several times with 50% methyl alcohol to obtain colorless needle-shaped crystals. The yield was 56.9%.

Production Example 45 Method for producing m-aminobenzoic acid ethyl ester-N-cellobioside 1.7 parts of m-aminobenzoic acid ethyl ester, 3.4 parts of cellobiose, 13 parts of water, and 1.4 parts of glacial acetic acid in 7 parts of ethyl alcohol. and heat condensation under reflux.

If the reaction solution is left in the refrigerator, crystals will precipitate. The reaction solution is filtered, the crystals are washed with ether, and recrystallized several times from 30% ethyl alcohol to obtain colorless needle-shaped crystals. The yield was 24.4%. Production Example 46 m-aminobenzoic acid propyl ester N-se.

Production method of piocid: m-aminobenzoic acid propyl ester 1.7 hours, cellopiose 3.4 hours, water 15 hours, acetic acid 1 hour
．． Add 4' to 15' ethyl alcohol under reflux,
Heat condensation.

If the reaction solution is left in the refrigerator, crystals will precipitate. The reaction solution is filtered, the crystals are washed with ether, and the crystals are washed several times with 94% ethyl alcohol to obtain colorless needle-shaped crystals. The yield was 2.0%.

Production Example 47 Method for producing m-aminobenzoic acid butyl ester - N-D-riboside 1.9 m-aminobenzoic acid butyl ester, 1.5 m of D-ribose, and 0.2 m of ammonium chloride are dissolved in 20% 94% ethyl alcohol. Add the mixture and heat to condense under reflux.

If the reaction solution is left in the refrigerator, crystals will precipitate. The reaction solution is filtered, the crystals are washed with ether, and recrystallized several times from 50% methyl alcohol to obtain colorless needle-like crystals. The yield was 3.7%.

[Brief explanation of drawings]

1 to 41 show infrared absorption spectra of the following aminobenzoic acid derivatives according to the present invention. Figure 1 - o-aminobenzoic acid-N-2-deoxy-D-riboside, Figure 2 - o-aminobenzoic acid, sodium fragrant
N-2-deoxy D-riboside, Figure 3 ~o-ami/
Benzoic acid-N-L-fucoside, Figure 4~o-Sodium aminobenzoate-N-L-fucoside, Figure 5~o-
Aminobenzoic acid-N-N-acetyl-D-glucosaminide, Figure 6 ~o-amino/sodium benzoate-N-N-
Acetyl-D-glucosaminide, Fig. 7 - o-aminobenzoic acid mono-N-maltoside, Fig. 8 - o-sodium aminobenzoate - N-maltoside, Fig. 9 - o-aminobenzoic acid-N-cellobioside, Fig. 10 ~Sodium o-aminobenzoate -N-cellobioside, Figure 11~
o-Aminobenzoic acid-N-lactosid, Figure 12~o
-Sodium aminobenzoate 1N-lactosid, 1st
Figure 3 ~ o-aminobenzoic acid-N-maltotrioside,
Figure 14 - Sodium o-aminobenzoate -N-maltotrioside, Figure 15 - o-aminobenzoic acid methyl ester -N-D-riboside, Figure 16 - o-aminobenzoic acid methyl ester -N-L-fucoside, Figure 17 - o-aminobenzoic acid methyl ester -N-N-acetyl-D-glucosaminide, Figure 18 - o-aminobenzoic acid methyl ester -N-maltoside, Figure 19 - o-aminobenzoic acid methyl ester-N-cellobioside, Figure 20 ~ o-aminobenzoic acid methyl ester N-lactoside, Figure 21 ~ o-aminobenzoic acid methyl ester - N-maltotrioside, Figure 22 ~ o-aminobenzoic acid ethyl ester N-D-riboside, Figure 23 ~ o-Ami/ethyl benzoate N-L fucoside, Figure 24 ~ o-Ami/ethyl benzoate N
- Cellobioside, Fig. 25 - o-Aminobenzoic acid butyl ester -N-D-riboside, Fig. 26 - o - Aminobenzoic acid butyl ester -N-L-fucoside, Fig. 27 -
o-Aminobenzoic acid butyl ester-N-cellobioside, Fig. 28 - m-aminobenzoic acid-N-L-fucoside, Fig. 29 - m-aminobenzoic acid-N-L-sodium
- Fucoside, Fig. 30 - m-amino/benzoic acid-N-acetyl-D-glucosaminide, Fig. 31 - m-sodium aminobenzoate -N-N-acetyl-D-glucosaminide, Fig. 32 - m-aminobenzoic acid - N-maltoside, Fig. 33 - m-sodium aminobenzoate-N-maltoside, Fig. 34 - m-aminobenzoic acid-N-cellobioside, Fig. 35 - m-sodium aminobenzoate-N-cellobioside, Fig. 36 - m- Aminobenzoic acid-
N-Lactoside, Figure 37 ~ Sodium m-aminobenzoate-N-Lactoside, Figure 38 ~ m-Aminobenzoic acid-N-maltotrioside, Figure 39 ~ Sodium m-aminobenzoate-N-maltotrioside, 40th
Figure 41 - m-aminobenzoic acid ethyl ester-N-L-fucoside, Figure 41 - m-aminobenzoic acid ethyl ester-N-cellobioside. Figure 1 Figure 2 Figure 3 Figure 4 Figure 5 Figure 6 Figure 7 Figure 8 Figure 9 Figure 10 Figure 11 Figure 12 Figure 13 Figure 14 Figure 15 Figure 16 Figure 17 Figure 18 Figure 19 Figure 20 Figure 21 Figure 22 Figure 23 Figure 24 Figure 25 Figure 26 Figure 27 Figure 28 Figure 29 Figure 30 Figure 31 Figure 32 Figure 33 Figure 34Figure 35Figure 36Figure 37Figure 38Figure 39Figure 40Figure 41

Claims (1)

[Claims] 1 General formula (I) ▲ Numerical formulas, chemical formulas, tables, etc. R_1-NH
- The group is in the ortho or meta position. ] or a pharmaceutically acceptable salt or alkyl ester thereof as an active ingredient. 2. The anti-inflammatory agent according to claim 1, wherein R_1 in the above formula (I) is ribose, deoxyribose, fucose, acetylglucosamine, maltose, cellobiose, lactose, or maltotriose. 3. The anti-inflammatory agent according to claim 1, wherein the salt is a Na salt. 4. The anti-inflammatory agent according to claim 1, wherein the ester is a methyl, ethyl or butyl ester.