CN105085511B - A kind of new aztreonam compound - Google Patents
A kind of new aztreonam compound Download PDFInfo
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- CN105085511B CN105085511B CN201510284727.1A CN201510284727A CN105085511B CN 105085511 B CN105085511 B CN 105085511B CN 201510284727 A CN201510284727 A CN 201510284727A CN 105085511 B CN105085511 B CN 105085511B
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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Abstract
The present invention relates to a kind of new aztreonam compound and preparation method thereof, belong to pharmaceutical technology field.New aztreonam compound provided by the invention, characteristic peak is shown at 2 θ is 7.83 ± 0.1 °, 10.21 ± 0.1 °, 14.37 ± 0.1 °, 19.42 ± 0.1 ° in the X ray powder diffractions obtained using Cu Ka radionetric surveys, and Differential Scanning Calorimetry has an endothermic peak at 150 DEG C~180 DEG C.New aztreonam compound good fluidity of the present invention, can more meet the requirement of pharmaceutics, be more suitable for preparing various pharmaceutical preparations.The sterile powder injection stability being prepared by new aztreonam compound of the present invention is good, and is not added with any auxiliary material such as arginine, so as to improve drug safety and validity, reduces the incidence of adverse reaction.
Description
Technical field
The present invention relates to a kind of new compound and preparation method thereof, more particularly to a kind of new aztreonam compound and its
Preparation method, belong to pharmaceutical technology field.
Background technology
AZT (Aztreonam), chemical name：[2S- [2 α, 3 β (Z)]] -2 [[[1- (2- amino -4- thiazolyls) -2-
[(2- methyl -4- oxo -1- sulfo group -3- azetidinyls) amino] -2- oxos ethylidene] amino] oxygen] -2 Methylpropionic acid.
Molecular formula is C13H17N5O8S2, molecular weight 435.43.Chemical structural formula：
AZT is a kind of novel ss-lactam antibiotics of monoamides ring class.Antimicrobial spectrum mainly includes gram-negative bacteria,
Such as Escherichia coli, klebsiella bacillus, serratia marcecens, proteus mirabilis, indole-positive proteus, citrobacter, stream
Haemophilus influenza, Pseudomonas aeruginosa and other pseudomonads, some Enterobacters, gonococcus etc..Do not absorb orally, be generally all made
Injection.Aztreonam for injection indication is suitable for the various infection caused by the sensitive aerobic gram-negative bacteria for the treatment of, such as：Urinary tract
The skin soft tissue such as infection, ALRI, septicemia, intraperitoneal infection, gynecological infection, postoperative wound and burn, ulcer
Infection etc..
The Main Ingredients and Appearance of aztreonam for injection is AZT, and auxiliary material is arginine, and its character is white or off-white powder
Or loose block.Preparation specification：0.5g、1.0g、2.0g.The allotment of drip-feed parenteral solution：Per 1g AZTs at least with note
Penetrate and dissolved with water 3ml, then (glucose injection of 0.9% sodium chloride injection, 5% or 10% or woods grignard are noted with appropriate transfusion
Penetrate liquid) dilute, AZT concentration must not exceed 2%, instil minute time 20-60.
In the prior art, AZT raw material has α, beta crystal, and alpha-crystal form is aqueous crystal formation, generally the water containing 7-14%, in water
In it is readily soluble, also the easy moisture absorption, stability are poor.AZT is often converted into beta crystal in raw material production, beta crystal is anhydrous, nonhygroscopic,
Density is big, good fluidity, and property is stable, is best for preparation.But the beta crystal of AZT, particularly AZT is in water
Middle solubility is smaller, and dissolution velocity is also slow, and in order to ensure solubility and dissolution velocity, certain proportion essence ammonia is added in AZT
Acid is extremely necessary.
In the prior art, most of solved the above problems by adding arginine in beta crystal AZT, still
Due to the difference of aztreonam for injection preparation technology, all there is preparation stabilization sex chromosome mosaicism.In addition, arginine also has one to human body
Determine side effect, most commonly seen in the form of parenteral solution, allergic reaction is most common arginine side effect, and liver or kidney have disease
The arginine side effect that is likely to occur of people it is more serious.
Therefore, clinically it is badly in need of developing a kind of safer, more stable aztreonam for injection product.
The content of the invention
Present invention aims at a kind of new aztreonam compound is provided, the aztreonam compound is a kind of different from existing
The aztreonam compound of the novel crystal forms of technology, and experiments prove that, the stability of the aztreonam compound of this kind of crystal formation is better than
Existing crystal formation, and any auxiliary material such as arginine need not be added when preparing aztreonam for injection, technique is simple, and repeatability is strong,
Clinical practice is safer.
To realize the object of the invention, using following technical scheme：
The present invention provides a kind of new aztreonam compound as shown in formula (I)：
The new aztreonam compound, in 2 θ in the X-ray powder diffraction collection obtained using Cu-Ka radionetric surveys
To show characteristic peak at 7.83 ± 0.1 °, 10.21 ± 0.1 °, 14.37 ± 0.1 °, 19.42 ± 0.1 °.
A kind of above-mentioned new aztreonam compound, the Differential Scanning Calorimetry of the new aztreonam compound is at 150 DEG C
~180 DEG C have an endothermic peak.
A kind of above-mentioned new aztreonam compound, the new aztreonam compound, the X- obtained using Cu-Ka radionetric surveys
In ray powder diffraction 2 θ be 7.84 ± 0.1 °, 8.91 ± 0.1 °, 9.32 ± 0.1 °, 10.21 ± 0.1 °, 12.56 ±
0.1°、12.84±0.1°、13.31±0.1°、13.54±0.1°、14.36±0.1°、14.71±0.1°、15.16±0.1°、
15.59±0.1°、16.53±0.1°、17.01±0.1°、17.68±0.1°、18.72±0.1°、19.43±0.1°、21.05
Characteristic peak is shown at ± 0.1 °, 21.93 ± 0.1 °, 23.08 ± 0.1 °, 23.49 ± 0.1 °.
A kind of above-mentioned new aztreonam compound, the Differential Scanning Calorimetry of the new aztreonam compound is 176 ± 3
There is endothermic peak at DEG C.
According to foregoing new aztreonam compound, wherein, the preparation method of the new aztreonam compound is including following
Step：
Aztreonam crude is added in DMA, is heated to backflow dissolving, then add necessarily into solution
The tetrahydrofuran of proportioning and ethyl acetate and then formation mixed solvent system, then cooling down crystallization, is filtered, washing, vacuum
Dry, obtain new aztreonam compound crystal formation.
The weight of the preparation method of above-mentioned new aztreonam compound, described aztreonam crude and DMA
Measure g：Volume ml ratios are 1：1.6~2.2.
The preparation method of above-mentioned new aztreonam compound, DMA, four in the mixed solvent system
The volume ml ratios of hydrogen furans and ethyl acetate are 8~11:0.9~1.5:5~8.
The preparation method of above-mentioned new aztreonam compound, described cooling down crystallization, its temperature are reduced to 0~10 DEG C.
The preparation method of above-mentioned new aztreonam compound, described washing, its solvent used are ethyl acetate, washing
Mode is that 300mL ethyl acetate washs in three times, each 100mL.
The preparation method of above-mentioned new aztreonam compound, described vacuum drying, temperature 65 used in its drying~
100℃。
Present invention also offers a kind of aztreonam for injection, is to be formed by above-mentioned new aztreonam compound through aseptic subpackaged
Powder-injection.
Above-mentioned aztreonam for injection, its preparation method comprise the following steps：
Aseptically, bottle washing procedure passes through soaks → ultrasonic washing → purified water shower by cillin bottle with purified water
After → ultrafiltration water shower → water for injection shower, automatically into tunnel oven, tunnel oven, which has, is incubated good casing, defeated
Send band, heating tube and laminar flow cleaning system composition, bottle on the conveyor belt, it is preheated after the sterilizing in more than 5 minutes of 320 DEG C of high temperature,
Less than 40 DEG C are cooled to, packing clean area is automatically fed into by conveyer belt, is used for packing；Plug is circulated through ultrasonic wave and purified water
Slightly wash → purified water and ultrasonic wave fine purifiation → water for injection fine purifiation → pure steam sterilizes → vacuumize hot air circulation drying → cooling
It is used to dispense button plug to less than 40 DEG C；Racking machine is dispensed using screw rod, computer control impulse ratio, quantitative that above-mentioned new ammonia is bent
Southern compound sterile bulk drug pours into bottle, and loading amount, bales catch plug are spot-check using assay balance；The cillin bottle of plug is buckled well, is delivered to
Lid process is rolled, Cover-rolling machine is screened aluminium lid by oscillator, and it is good and be buckled with the bottle of plug to be buckled in packing one by one, and dog is by aluminium lid
Tighten, deliver to lamp inspection desk, be sent into packaging process after lamp inspection is qualified, after packaging process labeling, through mounted box cartonning of examining goods, joint sealing is
For finished product.
In a word, the present inventor is by many experiments, by the strict control to crystallization processes parameter, unexpectedly obtain with
The aztreonam compound of the different novel crystal forms of prior art.It is can be seen that by 1-3 of the embodiment of the present invention prepared by the present invention
Obtained new aztreonam compound good fluidity, can more meet the requirement of pharmaceutics, be more suitable for preparing various medicine systems
Agent.The aseptic powder being prepared by new aztreonam compound of the present invention can be seen that by 4-6 of the embodiment of the present invention
Injection stability is good, and is not added with any auxiliary material such as arginine, so as to improve drug safety and validity, reduces bad
The incidence of reaction.
Brief description of the drawings
The X-ray powder diffraction collection of AZT crystal formation described in Fig. 1 embodiment of the present invention 1
The DSC spectrograms of AZT crystal formation described in Fig. 2 embodiment of the present invention 1
Embodiment
The present invention is described in further detail below by embodiment, but is only intended to help and understands this hair
It is bright, professional and technical personnel in the field is realized or using the present invention, any restrictions are not formed to the present invention.
Embodiment 1 prepares new aztreonam compound of the present invention
Aztreonam crude 1000g is added in 5L there-necked flasks, adds DMA 2000mL, stirs, is heated to
Backflow dissolving, then 200mL tetrahydrofurans and 1200mL ethyl acetate are added into solution, then slow cooling is cooled to 5 DEG C, stirs
Crystallization is mixed, is filtered, 300mL ethyl acetate washs in three times, each 100mL, 65 DEG C of vacuum drying, obtains AZT dry product
968g, yield 96.8%.
The X-ray powder diffraction figure of new aztreonam compound prepared by the present embodiment is in the θ of angle of reflection 2 for (precision is
±0.1°)：7.84,8.91,9.32,10.21,12.56,12.84,13.31,13.54,14.36,14.71,15.16,15.59,
There is characteristic absorption peak at 16.53,17.01,17.68,18.72,19.43,21.05,21.93,23.08,23.49, such as Fig. 1 institutes
Show.
Its DSC collection of illustrative plates nearby has endothermic peak (precision is ± 3 DEG C) at 176 DEG C, as shown in Figure 2.
Embodiment 2 prepares new aztreonam compound of the present invention
Aztreonam crude 1000g is added in 5L there-necked flasks, adds DMA 2200mL, stirs, is heated to
Backflow dissolving, then 300mL tetrahydrofurans and 1600mL ethyl acetate are added into solution, then slow cooling is cooled to 0 DEG C, stirs
Crystallization is mixed, is filtered, 300mL ethyl acetate washs in three times, each 100mL, 100 DEG C of vacuum drying, obtains AZT dry product
925g, yield 92.5%.
Embodiment 3 prepares new aztreonam compound of the present invention
Aztreonam crude 1000g is added in 5L there-necked flasks, adds DMA 1600mL, stirs, is heated to
Backflow dissolving, then 180mL tetrahydrofurans and 1000mL ethyl acetate are added into solution, then slow cooling is cooled to 10 DEG C,
Stirring and crystallizing, filtering, 300mL ethyl acetate wash in three times, each 100mL, 80 DEG C of vacuum drying, obtain AZT dry product
939g, yield 93.9%.
Embodiment 4 prepares aztreonam for injection of the present invention, specification：0.5g
Prescription：
Preparation method：
Aseptically, bottle washing procedure passes through soaks → ultrasonic washing → purified water shower by cillin bottle with purified water
After → ultrafiltration water shower → water for injection shower, automatically into tunnel oven, tunnel oven, which has, is incubated good casing, defeated
Send band, heating tube and laminar flow cleaning system composition, bottle on the conveyor belt, it is preheated after the sterilizing in more than 5 minutes of 320 DEG C of high temperature,
Less than 40 DEG C are cooled to, packing clean area is automatically fed into by conveyer belt, is used for packing；Plug is circulated through ultrasonic wave and purified water
Slightly wash → purified water and ultrasonic wave fine purifiation → water for injection fine purifiation → pure steam sterilizes → vacuumize hot air circulation drying → cooling
It is used to dispense button plug to less than 40 DEG C；Racking machine is dispensed using screw rod, computer control impulse ratio, quantitative to be made in embodiment 1
Standby AZT crystal formation sterile raw material pours into bottle, and loading amount, bales catch plug are spot-check using assay balance；The cillin bottle of plug is buckled well,
Deliver to and roll lid process, Cover-rolling machine is screened aluminium lid by oscillator, is buckled in packing one by one well and is buckled with the bottle of plug, and dog will
Aluminium lid is tightened, and delivers to lamp inspection desk, and packaging process is sent into after lamp inspection is qualified, after packaging process labeling, through mounted box cartonning of examining goods, envelope
Case is finished product.
Embodiment 5 prepares aztreonam for injection of the present invention, specification：1.0g
Prescription：
Preparation method：
Aseptically, bottle washing procedure passes through soaks → ultrasonic washing → purified water shower by cillin bottle with purified water
After → ultrafiltration water shower → water for injection shower, automatically into tunnel oven, tunnel oven, which has, is incubated good casing, defeated
Send band, heating tube and laminar flow cleaning system composition, bottle on the conveyor belt, it is preheated after the sterilizing in more than 5 minutes of 320 DEG C of high temperature,
Less than 40 DEG C are cooled to, packing clean area is automatically fed into by conveyer belt, is used for packing；Plug is circulated through ultrasonic wave and purified water
Slightly wash → purified water and ultrasonic wave fine purifiation → water for injection fine purifiation → pure steam sterilizes → vacuumize hot air circulation drying → cooling
It is used to dispense button plug to less than 40 DEG C；Racking machine is dispensed using screw rod, computer control impulse ratio, quantitative to be made in embodiment 2
Standby AZT crystal formation sterile raw material pours into bottle, and loading amount, bales catch plug are spot-check using assay balance；The cillin bottle of plug is buckled well,
Deliver to and roll lid process, Cover-rolling machine is screened aluminium lid by oscillator, is buckled in packing one by one well and is buckled with the bottle of plug, and dog will
Aluminium lid is tightened, and delivers to lamp inspection desk, and packaging process is sent into after lamp inspection is qualified, after packaging process labeling, through mounted box cartonning of examining goods, envelope
Case is finished product.
Embodiment 6 prepares aztreonam for injection of the present invention, specification：2.0g
Prescription：
Preparation method：
Aseptically, bottle washing procedure passes through soaks → ultrasonic washing → purified water shower by cillin bottle with purified water
After → ultrafiltration water shower → water for injection shower, automatically into tunnel oven, tunnel oven, which has, is incubated good casing, defeated
Send band, heating tube and laminar flow cleaning system composition, bottle on the conveyor belt, it is preheated after the sterilizing in more than 5 minutes of 320 DEG C of high temperature,
Less than 40 DEG C are cooled to, packing clean area is automatically fed into by conveyer belt, is used for packing；Plug is circulated through ultrasonic wave and purified water
Slightly wash → purified water and ultrasonic wave fine purifiation → water for injection fine purifiation → pure steam sterilizes → vacuumize hot air circulation drying → cooling
It is used to dispense button plug to less than 40 DEG C；Racking machine is dispensed using screw rod, computer control impulse ratio, quantitative to be made in embodiment 3
Standby AZT crystal formation sterile raw material pours into bottle, and loading amount, bales catch plug are spot-check using assay balance；The cillin bottle of plug is buckled well,
Deliver to and roll lid process, Cover-rolling machine is screened aluminium lid by oscillator, is buckled in packing one by one well and is buckled with the bottle of plug, and dog will
Aluminium lid is tightened, and delivers to lamp inspection desk, and packaging process is sent into after lamp inspection is qualified, after packaging process labeling, through mounted box cartonning of examining goods, envelope
Case is finished product.
Product prepared by the present invention, its mobility, stability are significantly increased compared with commercially available product.
The mobility of test example 1 compares
Angle of repose is the most easy method for examining powder fluidity quality, and angle of repose is smaller, illustrates that frictional force is smaller, stream
Dynamic property is better.This experiment is bent using the ammonia prepared by injection method (fixed funnel method) measure embodiment 1, embodiment 2 and embodiment 3
Southern material sample and the angle of repose of AZT raw material commercially available product 1, commercially available product 2 and commercially available product 3.Testing sample is poured into funnel, made
Its lightly, equably fall into disc centre, a cone is formed, when material freely falls along disk border from powder hypotenuse
Stop charging when lower, determine angle of repose with protractor, measurement result is shown in Table 1.As a result product mobility prepared by the present invention is shown
More preferably, better than commercially available product.Commercially available product 1, commercially available product 2 and commercially available product 3 are the AZT raw material of beta crystal.
The angle of repose measurement result of table 1
| Sample | Embodiment 1 | Embodiment 2 | Embodiment 3 | Commercially available product 1 | Commercially available product 2 | Commercially available product 3 |
| Angle of repose | 29.8 | 31.6 | 32.2 | 43.1 | 45.6 | 43.9 |
The study on the stability of test example 2
Sample and aztreonam for injection commercially available product A prepared by embodiment 4, embodiment 5 and embodiment 6 carry out acceleration examination
Test, accelerated test condition is under conditions of 40 ± 2 DEG C of temperature, relative humidity 75 ± 5%, is placed 3 months.Commercially available product A is β brilliant
Powder-injection prepared by the AZT raw material of type, and with the addition of auxiliary material arginine.
Content and detection method about material are official method (Chinese Pharmacopoeia version two in 2010).
The accelerated test of table 2
The Chinese Pharmacopoeia quality standard that aztreonam for injection has been expressly recited in version two in 2010, it is desirable to which content is
90.0%-115.0%, relevant thing list is miscellaneous to cannot be greater than 1.5%, and relevant thing is always miscellaneous to cannot be greater than 5.0%.
From table 2：Compared with commercially available product A, the sample size prepared by embodiment 4-6 is higher, and relevant thing is lower.Pass through
After 3 months accelerated tests, the sample size prepared by embodiment 4-6 reduces slower, and content is more than 105%, relevant thing
Increase slower, the relevant miscellaneous content of thing list below 1%, relevant thing always miscellaneous content below 4%；And commercially available product A is adding
When fast 2 months, just there is situation off quality, content is less than 90%, and the miscellaneous content of relevant thing list is relevant more than 1.5%
Always miscellaneous content is more than 5.0% to thing.Result above shows that the stability of the sample prepared by 4-6 of the embodiment of the present invention is more preferable.
It the above is only the preferred embodiment of the present invention, be not intended to limit the invention, come for those skilled in the art
Say, under the premise without departing from the principles of the invention, some improvement that can also make, retouching, equivalent substitution, should be included in this
Within the protection domain of invention.
Claims (4)
1. a kind of new aztreonam compound as shown in formula (I),
Characterized in that, the new aztreonam compound, in the X-ray powder diffraction collection obtained using Cu-Ka radionetric surveys
2 θ be 7.84 ± 0.1 °, 8.91 ± 0.1 °, 9.32 ± 0.1 °, 10.21 ± 0.1 °, 12.56 ± 0.1 °, 12.84 ± 0.1 °,
13.31±0.1°、13.54±0.1°、14.36±0.1°、14.71±0.1°、15.16±0.1°、15.59±0.1°、16.53
±0.1°、17.01±0.1°、17.68±0.1°、18.72±0.1°、19.43±0.1°、21.05±0.1°、21.93±
Characteristic peak is shown at 0.1 °, 23.08 ± 0.1 °, 23.49 ± 0.1 °；The Differential Scanning Calorimetry of the new aztreonam compound
There is endothermic peak at 176 ± 3 DEG C.
2. a kind of preparation method of new aztreonam compound as claimed in claim 1, it is characterised in that including following step
Suddenly：
Aztreonam crude is added in DMA, is heated to backflow dissolving, then certain proportioning is added into solution
Tetrahydrofuran and ethyl acetate so that form mixed solvent system, then cooling down crystallization, is filtered, and is washed, vacuum drying,
Obtain new aztreonam compound crystal formation；Wherein, the weight g of the aztreonam crude and DMA：Volume mL
Than for 1：1.6~2.2；The volume mL of DMAC N,N' dimethyl acetamide, tetrahydrofuran and ethyl acetate in the mixed solvent system
Than for 8~11:0.9~1.5:5~8；The cooling down crystallization, its temperature are reduced to 0~10 DEG C；The washing, what it was used
Solvent is ethyl acetate, and mode of washing is that 300mL ethyl acetate washs in three times, each 100mL；The vacuum drying, it is dry
65~100 DEG C of temperature used in dry.
3. a kind of aztreonam for injection, it is characterised in that the aztreonam for injection is bent by new ammonia as claimed in claim 1
Southern compound is through the aseptic subpackaged powder-injection formed.
4. a kind of preparation method of aztreonam for injection as claimed in claim 3, it is characterised in that comprise the following steps：
Aseptically, bottle washing procedure is super by cillin bottle to be soaked to → ultrasonic washing → purified water shower → with purified water
After drainage shower → water for injection shower, good casing, conveying are incubated automatically into tunnel oven, tunnel oven has
Band, heating tube and laminar flow cleaning system composition, on the conveyor belt, preheated rear 320 DEG C of high temperature sterilize, are cold bottle for more than 5 minutes
But to less than 40 DEG C, packing clean area is automatically fed into by conveyer belt, used for packing；Plug is thick through ultrasonic wave circulation and purified water
Wash → purified water and ultrasonic wave fine purifiation → water for injection fine purifiation → pure steam sterilizes → vacuumize hot air circulation and dry → be cooled to
Less than 40 DEG C are used to dispense button plug；Racking machine is dispensed using screw rod, computer control impulse ratio, quantitative by above-mentioned new AZT
Compound sterile bulk drug pours into bottle, and loading amount, bales catch plug are spot-check using assay balance；The cillin bottle of plug is buckled well, delivers to and rolls
Lid process, Cover-rolling machine are screened aluminium lid by oscillator, are buckled in packing one by one well and are buckled with the bottle of plug, dog rolls aluminium lid
Tightly, lamp inspection desk is delivered to, is sent into packaging process after lamp inspection is qualified, after packaging process labeling, through mounted box cartonning of examining goods, joint sealing is
Finished product.
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| CN112645943A (en) * | 2020-12-25 | 2021-04-13 | 南京华盖制药有限公司 | Preparation method of ammonia-containing qunan amorphous system |
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| 氨曲南的合成;张秋 等;《中国新药杂志》;20081231;第17卷(第5期);第393-395页；第395页右栏第1段 * |
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