CN104892507B - Water-soluble methanesulfonic acid sarafloxacin and preparation method thereof - Google Patents
Water-soluble methanesulfonic acid sarafloxacin and preparation method thereof Download PDFInfo
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- CN104892507B CN104892507B CN201510276352.4A CN201510276352A CN104892507B CN 104892507 B CN104892507 B CN 104892507B CN 201510276352 A CN201510276352 A CN 201510276352A CN 104892507 B CN104892507 B CN 104892507B
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
- C07D215/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3 with oxygen atoms in position 4
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
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Abstract
The invention belongs to chemosynthesis technical fields, and in particular to water-soluble methanesulfonic acid sarafloxacin and preparation method thereof.Methanesulfonic acid sarafloxacin proposed by the present invention, has the following structure：
Description
Technical field
The invention belongs to chemosynthesis technical fields, and in particular to water-soluble methanesulfonic acid sarafloxacin and preparation method thereof.
Background technology
Sarafloxacin (sarafloxacin), the fluoro- 1- of also known as 6- (4- fluorophenyls)-Isosorbide-5-Nitrae-dihydro -4- oxos -7- (1- piperazines
Piperazine base) -3- quinoline carboxylic acids；English is：6-Fluoro-1-(4-fluorophenyl)-1,4-dihydro-4-oxo-7-(1-
piper-azinyl)-3-quinolinecarboxylic acid；It is developed in nineteen ninety-five by Abbott of the U.S. and in the U.S.
Listing, is first fluoroquinolones for being approved by the fda in the United States for food animal, has has a broad antifungal spectrum, antibacterial activity
By force, the characteristics of with other antimicrobials without cross resistance, (WOLFSON J S, HOOPER D C, newest broad spectrum quinolone class resisted micro-
Biological medicament [M], Jiang Suchun, Song Keyi, Beijing：People's Medical Officer Press, 1991,26-45).China was approved as state in 2001
Two kind new medicines of family, Market Feedback work well.Clinically usually used is hydrochloric acid sarafloxacin, is animal specific fluoquinolone
Class drug has good killing effect to gram-positive bacteria, negative bacterium, anaerobic bacteria, mycoplasma, Chlamydia, can be used for pre-
Prevent and treat various bacteriosis, such as pig, the colibacillosis of chicken, salmonellosis, mycoplasmosis and staphylococcic sense
Dye, it can also be used to aquatic livestock, silkworm sensitive bacteria infectious diseases (old cane pomegranate, veterinary pharmacology [M], the third edition, Beijing：In
Agricultural publishing house of state, 2009；Wang Yuhua, He Rongfan, health state equality, hydrochloric acid sarafloxacin capsule is to silkworm bacteremic septicemia
Study on prevention [J], sericulture science, 2010,36 (6)：977-983).
Either sarafloxacin or hydrochloric acid sarafloxacin due to their poorly water-solubles, mildly bitter flavor, have and draw moist and physics and chemistry
The special natures such as property is unstable, this greatly limits practical promotion and application (Wu Chunli, Hu Yurong, Du clinically
It is refined etc., the study on the synthesis [J] of hydrochloric acid sarafloxacin, Henan chemical industry, 2004 (11)：16-18).Thus, it is managed using drug design
It reads, sarafloxacin original structure is kept not change, carry out the structural modification of new type water-solubility sarafloxacin, be to improve sarafloxacin
It is the important channel realized sarafloxacin clinical application, expand preparation type with the elementary tactics of hydrochloric acid sarafloxacin raw material.
Invention content
The technical problem to be solved by the present invention is to sarafloxacin, hydrochloric acid sarafloxacin poorly water-solubles.
The technical scheme is that methanesulfonic acid sarafloxacin, has the following structure：
The present invention also provides the preparation methods of methanesulfonic acid sarafloxacin, include the following steps：
A. hydrochloric acid sarafloxacin is dissolved in the water, pH to 7.5 is adjusted with sodium hydroxide, solid is precipitated, filtering is collected husky
Draw husky star solid；
B. sarafloxacin solid is dissolved in organic solution, methanesulfonic acid is added under the conditions of being heated to 30~120 DEG C, stirred
0.5~2.0 hour, crystallization is set to be precipitated within cooling 5~20 hours, it is collected by filtration, it is used in combination organic solvent II to wash 3 times, vacuum
It is dry to get to methanesulfonic acid sarafloxacin target product；The organic solution is that organic solvent I is mixed to get with water.
Further, when organic solvent I described in step b is mixed with water, the weight ratio of organic solvent I and water be 1 ︰ 0~
0.2。
Further, organic solvent I described in step b refer to ethyl alcohol, isopropanol, propylene glycol, acetonitrile, Isosorbide-5-Nitrae-dioxane and
At least one of tetrahydrofuran；The volume ratio of organic solvent between any two is 0~1.0 ︰ 1.0~0, and organic solvent total volume
It is not 0.
Further, the addition of methanesulfonic acid described in step b mole is 1~1.5 times of sarafloxacin mole.
Further, organic solvent II described in step b refers to ethyl alcohol, isopropanol, propylene glycol, acetonitrile, Isosorbide-5-Nitrae-dioxane
At least one of with tetrahydrofuran；The volume ratio of organic solvent between any two is 0~1.0 ︰ 1.0~0, and organic solvent is overall
Product is not 0.
The present invention also provides purposes of the methanesulfonic acid sarafloxacin in preparing animal antimicrobial.
The present invention also provides purposes of the preparation method of the methanesulfonic acid sarafloxacin in preparing animal antimicrobial.
Beneficial effects of the present invention：Methanesulfonic acid sarafloxacin has the water solubility for being better than hydrochloric acid sarafloxacin；It keeps simultaneously
Has a broad antifungal spectrum, antibacterial activity possessed by hydrochloric acid sarafloxacin be strong, with other antimicrobials without cross resistance the characteristics of.Target
Product is better than hydrochloric acid sarafloxacin in terms of mycoplasma is prevented, infects streptococcosis and colibacillosis treatment, has preferable
Application prospect.The present invention provides the preparation methods for the methanesulfonic acid sarafloxacin that can be used for Animal diseases treatment, improve
Traditional hydrochloric acid sarafloxacin is water-soluble, provide novel sarafloxacin derivative and its in pharmacy and additive agent field
Using.
Specific implementation mode
The preparation of 1 methanesulfonic acid sarafloxacin of embodiment
Hydrochloric acid sarafloxacin is dissolved in the water, pH to 7.5 or so is adjusted with sodium hydroxide, solid is precipitated, filter, collect
Sarafloxacin solid.
Sarafloxacin (1mol) solid is dissolved in the mixed solvent of ethyl alcohol and water (ethyl alcohol is 1 ︰ 0.05 with water weight ratio)
In, it is heated to adding the methanesulfonic acid that molal quantity is 1 times of sarafloxacin under the conditions of 80 DEG C, stir 2.0 hours, make knot within cooling 10 hours
Partial crystallization goes out, collected by filtration, and ethyl alcohol is used in combination to wash 1~3 time, and vacuum drying is to get to target product.White crystals, yield
92%, fast atom bombardment MS MS (FAB)：m/e 481.39(M+)、385.37(M+-CH3SO3H), with target product methylsulphur
The molecular weight calculated value of sour sarafloxacin is 481.47 consistent.
The preparation of 2 methanesulfonic acid sarafloxacin of embodiment
Hydrochloric acid sarafloxacin is dissolved in the water, pH to 7.5 or so is adjusted with sodium hydroxide, solid is precipitated, filter, collect
Sarafloxacin solid.
The mixing that sarafloxacin (1mol) solid is dissolved in isopropanol and water (isopropanol is 1 ︰ 0.1 with water weight ratio) is molten
In agent, it is heated to adding the methanesulfonic acid that molal quantity is 1.2 times of sarafloxacin under the conditions of 90 DEG C, stirs 0.5 hour, it is 20 hours cooling
Crystallization is set to be precipitated, it is collected by filtration, it is used in combination acetonitrile to wash 1~3 time, vacuum drying is to get to target product.White crystals,
Yield 91.5%, MS (FAB)：m/e 481.43(M+)、385.28(M+-CH3SO3H), with target product methanesulfonic acid sarafloxacin
Molecular weight calculated value be 481.47 consistent.
The preparation of 3 methanesulfonic acid sarafloxacin of embodiment
Hydrochloric acid sarafloxacin is dissolved in the water, pH to 7.5 or so is adjusted with sodium hydroxide, solid is precipitated, filter, collect
Sarafloxacin solid.
Sarafloxacin (1mol) solid is dissolved in acetonitrile solvent, it is that salad is husky that molal quantity is added under the conditions of being heated to 65 DEG C
The methanesulfonic acid that 1.5 times of star stirs 0.5 hour, so that crystallization is precipitated within cooling 20 hours, collected by filtration, and isopropanol is used in combination to wash 1
~3 times, vacuum drying is to get to target product.White crystals, yield 88.4%, MS (FAB)：m/e 482.02(M+)、
385.44(M+-CH3SO3H), it is 481.47 consistent with the molecular weight calculated value of target product methanesulfonic acid sarafloxacin.
The preparation of 4 methanesulfonic acid sarafloxacin of embodiment
Hydrochloric acid sarafloxacin is dissolved in the water, pH to 7.5 or so is adjusted with sodium hydroxide, solid is precipitated, filter, collect
Sarafloxacin solid.
Sarafloxacin (1mol) solid is dissolved in 1,4- dioxane, and (1,4- dioxane is 1 ︰ with water weight ratio with water
0.15) in the mixed solvent is heated to adding the methanesulfonic acid that molal quantity is 1 times of sarafloxacin under the conditions of 120 DEG C, and stirring 0.5 is small
When, so that crystallization is precipitated within cooling 8 hours, it is collected by filtration, organic solvent ethyl alcohol and Isosorbide-5-Nitrae-dioxane (ethyl alcohol and Isosorbide-5-Nitrae-is used in combination
Dioxane volume ratio is 1.0 ︰ 1.0) mixed solvent washs 1~3 time, and vacuum drying is to get to target product.White crystals,
Yield 89.32%, MS (FAB)：m/e 481.77(M+)、385.41(M+-CH3SO3H), with target product methanesulfonic acid sarafloxacin
Molecular weight calculated value be 481.47 consistent.
The preparation of 5 methanesulfonic acid sarafloxacin of embodiment
Hydrochloric acid sarafloxacin is dissolved in the water, pH to 7.5 or so is adjusted with sodium hydroxide, solid is precipitated, filter, collect
Sarafloxacin solid.
Sarafloxacin (1mol) solid is dissolved in the mixed of tetrahydrofuran and water (tetrahydrofuran is 1 ︰ 0.1 with water weight ratio)
In bonding solvent, it is heated to adding the methanesulfonic acid that molal quantity is 1.5 times of sarafloxacin under the conditions of 30 DEG C, stirs 2.0 hours, cooling 20
Hour crystallization is made to be precipitated, it is collected by filtration, be used in combination ethyl alcohol and isopropanol (ethyl alcohol and isopropanol volume ratio be 0.5 ︰ 1.0) to mix
Solvent washs 1~3 time, and vacuum drying is to get to target product.White crystals, yield 76.32%, MS (FAB)：m/e
481.11(M+)、385.26(M+-CH3SO3H), the molecular weight calculated value with target product methanesulfonic acid sarafloxacin is
481.47 consistent.
The preparation of 6 methanesulfonic acid sarafloxacin of embodiment
Hydrochloric acid sarafloxacin is dissolved in the water, pH to 7.5 or so is adjusted with sodium hydroxide, solid is precipitated, filter, collect
Sarafloxacin solid.
Sarafloxacin (1mol) solid is dissolved in isopropanol solvent, it is salad that molal quantity is added under the conditions of being heated to 30 DEG C
The methanesulfonic acid that 1.5 times of husky star stirs 1.0 hours, so that crystallization is precipitated within cooling 15 hours, collected by filtration, and acetonitrile and four is used in combination
Hydrogen furans (acetonitrile and tetrahydrofuran volume ratio be 1.0 ︰ 0.5) mixed solvent washs 1~3 time, and vacuum drying is produced to get to target
Object.White crystals, yield 68.86%, MS (FAB)：m/e 481.89(M+)、385.64(M+-CH3SO3H), with target product first
The molecular weight calculated value of sulfonic acid sarafloxacin is 481.47 consistent.
The preparation of 7 methanesulfonic acid sarafloxacin of embodiment
Hydrochloric acid sarafloxacin is dissolved in the water, pH to 7.5 or so is adjusted with sodium hydroxide, solid is precipitated, filter, collect
Sarafloxacin solid.
Isosorbide-5-Nitrae-dioxane and tetrahydrofuran are by volume that 1.0 ︰ 1.0 are mixed, then with the water (weight of organic solvent and water
Than for 1 ︰ 0.12) mixing, obtain organic solution；Sarafloxacin (1mol) solid is dissolved in organic solution, 100 DEG C of items are heated to
The methanesulfonic acid that molal quantity is 1.2 times of sarafloxacin is added under part, is stirred 0.5 hour, so that crystallization is precipitated within cooling 5 hours, filtering is received
Collection crystallization, be used in combination the mixed solvent of isopropanol and tetrahydrofuran (isopropanol and tetrahydrofuran volume ratio be 1.0 ︰ 1.0) wash 1~
3 times, vacuum drying is to get to target product.White crystals, yield 81.05%, MS (FAB)：m/e 481.66(M+)、
385.28(M+-CH3SO3H), it is 481.47 consistent with the molecular weight calculated value of target product methanesulfonic acid sarafloxacin.
The preparation of 8 methanesulfonic acid sarafloxacin of embodiment
Hydrochloric acid sarafloxacin is dissolved in the water, pH to 7.5 or so is adjusted with sodium hydroxide, solid is precipitated, filter, collect
Sarafloxacin solid.
Isopropanol/Isosorbide-5-Nitrae-dioxane by volume be 1.0 ︰ 1.0 mix, then with the water (weight ratio of organic solvent and water
Example is 1 ︰ 0.2) mixing, obtain organic solution；Sarafloxacin (1mol) solid is dissolved in organic solution, 60 DEG C of conditions are heated to
Lower addition molal quantity is the methanesulfonic acid of 1.0 times of sarafloxacin, is stirred 2.0 hours, so that crystallization is precipitated within cooling 15 hours, is collected by filtration
Ethyl alcohol/Isosorbide-5-Nitrae-dioxane (ethyl alcohol is 1.0 ︰ 0.2 with Isosorbide-5-Nitrae-dioxane volume ratio) mixed solvent washing 1~3 is used in combination in crystallization
Secondary, vacuum drying is to get to target product.White crystals, yield 84.54%, MS (FAB)：m/e 481.29(M+)、385.46
(M+-CH3SO3H), it is 481.47 consistent with the molecular weight calculated value of target product methanesulfonic acid sarafloxacin.
The preparation of 9 methanesulfonic acid sarafloxacin of embodiment
Hydrochloric acid sarafloxacin is dissolved in the water, pH to 7.5 or so is adjusted with sodium hydroxide, solid is precipitated, filter, collect
Sarafloxacin solid.
It is mixed for 0.5 ︰ 1.0 according to propylene glycol/isopropanol volume ratio, then mixes the (weight ratio of organic solvent and water with water
It is 1 ︰ 0.1), obtain organic solution；Sarafloxacin (1mol) solid is dissolved in organic solution, is added under the conditions of being heated to 60 DEG C
Molal quantity is the methanesulfonic acid of 1.2 times of sarafloxacin, is stirred 2.0 hours, so that crystallization is precipitated within cooling 10 hours, collected by filtration,
It is used in combination propylene glycol/isopropanol (propylene glycol/isopropanol volume ratio is 1.0 ︰ 1.0) mixed solvent to wash 1~3 time, vacuum drying, i.e.,
Obtain target product.White crystals, yield 85.33%, MS (FAB)：m/e 481.81(M+)、385.42(M+-CH3SO3H), with
The molecular weight calculated value of target product methanesulfonic acid sarafloxacin is 481.47 consistent.
10 solubility test of embodiment
Sarafloxacin bulk pharmaceutical chemicals, hydrochloric acid sarafloxacin bulk pharmaceutical chemicals and methanesulfonic acid sarafloxacin bulk pharmaceutical chemicals are taken to be put into 50 millis respectively
It rises in volumetric flask, purified water is added to be configured to supersaturated solution, be placed in constant temperature blender with magnetic force and stir 2 hours, take 1 milliliter of supernatant
In 50 milliliters of volumetric flasks, it is diluted to scale, according to the absorbance that spectrophotometry measures, substitutes into standard curve regression equation,
The solubility of sarafloxacin in sample can be calculated.
It the results are shown in Table 1.Methanesulfonic acid sarafloxacin is compared with sarafloxacin and hydrochloric acid sarafloxacin as can be seen from Table 1,
Water solubility significantly improves many.
1 sarafloxacin of table, hydrochloric acid sarafloxacin and methanesulfonic acid sarafloxacin solubility
| Solubility mg/ml | |
| Sarafloxacin | 0.011 |
| Hydrochloric acid sarafloxacin | 0.79 |
| Methanesulfonic acid sarafloxacin | 6.26 |
The antibacterial activity in vitro of 11 main pathogenic bacteria of embodiment measures
Standard E. coli, Diplococcus pneumopniae, staphylococcus and bordetella bacilli are inoculated in nutrient broth enrichment liquid, 37
It DEG C is incubated overnight.Sterilized agar medium is heated to melt completely, is poured in culture dish, per ware 15ml (lower layer), is waited for
It is solidified.In addition, the PDA culture medium of thawing, which is cooled to 50 DEG C or so, is mixed into the above-mentioned several bacterium solutions of test organisms, bacterium will be mixed with
Culture medium 5ml is added on (upper layer) to be solidified on the culture medium solidified.It is directly vertically put in media surface with sterile working
Oxford cup is gently pressurizeed, and so that it is contacted tight with culture medium, 100 μ l of liquid to be checked are added in cup.It is small to set 37 DEG C of cultures 36
When, it observes as a result, inhibition zone size directly measures reading with ruler.
It the results are shown in Table 2.The result shows that：Methanesulfonic acid sarafloxacin is better than sarafloxacin and salt to the fungistatic effect of most bacteriums
Sour sarafloxacin.Three kinds of sarafloxacin, hydrochloric acid sarafloxacin and methanesulfonic acid sarafloxacin drugs are to bordetella bacilli without antibacterial work
With may have much relations with bordetella bacilli category Bacillus alcaligenes section.Sarafloxacin, hydrochloric acid sarafloxacin and methanesulfonic acid sarafloxacin
Three kinds of drugs generally influence the inhibition zone size of bacterium without conspicuousness；But consider from time angle, it is continuous with bacterium
Growth and antibiotic metabolism, during inhibiting Escherichia coli and salmonella and golden staphylococci, methanesulfonic acid sarafloxacin medicine
The duration is imitated better than sarafloxacin and hydrochloric acid sarafloxacin.Relative to leather such as Diplococcus pneumopniae, golden staphylococci and streptococcus
For Lan Shi positive bacterias, three kinds of sarafloxacin, hydrochloric acid sarafloxacin and methanesulfonic acid sarafloxacin drugs are to Escherichia coli, Salmonella
The effect of the Gram-negative bacterias such as bacterium and haemophilus antibacterial is better than gram-positive bacteria.
2 sarafloxacin of table, hydrochloric acid sarafloxacin and methanesulfonic acid sarafloxacin are to bacterium inhibition zone size (mm)
Claims (6)
1. methanesulfonic acid sarafloxacin, has the following structure：
2. the preparation method of methanesulfonic acid sarafloxacin described in claim 1, it is characterised in that：Include the following steps：
A. hydrochloric acid sarafloxacin is dissolved in the water, pH to 7.5 is adjusted with sodium hydroxide, solid is precipitated, it is husky to collect salad for filtering
Star solid；
B. sarafloxacin solid is dissolved in organic solution, adds methanesulfonic acid under the conditions of being heated to 30~120 DEG C, stirring 0.5~
2.0 hours, crystallization is set to be precipitated within cooling 5~20 hours, it is collected by filtration, the washing of organic solvent II is used in combination three times, vacuum drying,
Obtain methanesulfonic acid sarafloxacin target product；The organic solvent is that organic solvent I is mixed to get with water, organic solvent I
Weight ratio with water is 1 ︰ 0-0.2.
3. preparation method as claimed in claim 2, it is characterised in that：Organic solvent I described in step b refers to ethyl alcohol, isopropyl
At least one of alcohol, propylene glycol, acetonitrile, 1,4- dioxane and tetrahydrofuran；The volume ratio of organic solvent between any two is
0-1.0 ︰ 1.0-0, and organic solvent total volume is not 0.
4. preparation method as claimed in claim 2, it is characterised in that：It is salad that methanesulfonic acid described in step b, which adds mole,
1-1.5 times of husky star mole.
5. preparation method as claimed in claim 2, it is characterised in that：Organic solvent II described in step b refers to ethyl alcohol, isopropyl
At least one of alcohol, propylene glycol, acetonitrile, 1,4- dioxane and tetrahydrofuran；The volume ratio of organic solvent between any two is
0-1.0 ︰ 1.0-0, and organic solvent total volume is not 0.
6. purposes of the methanesulfonic acid sarafloxacin described in claim 1 in preparing animal antimicrobial.
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Address after: No. 1, Jiuxu Avenue, Suining Economic Development Zone, Xuzhou City, Jiangsu Province, 221200 Patentee after: Xuzhou Tianyi Animal Pharmaceutical Co.,Ltd. Address before: 221200 Xuzhou Suining South Ring Road Industrial Park A Patentee before: XUZHOU TIANYI ANIMAL PHARMACEUTICAL CO.,LTD. |