CN105693920A - Preparation method of long-term-development in-situ-gelation temperature-sensitive liquid embolic material - Google Patents

Preparation method of long-term-development in-situ-gelation temperature-sensitive liquid embolic material Download PDF

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CN105693920A
CN105693920A CN201610076134.0A CN201610076134A CN105693920A CN 105693920 A CN105693920 A CN 105693920A CN 201610076134 A CN201610076134 A CN 201610076134A CN 105693920 A CN105693920 A CN 105693920A
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preparation
development
situ
water
nipa
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CN105693920B (en
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朱肖杰
孟建文
朱小敏
李红梅
张素文
郈秀菊
王晓晨
罗西友
王传栋
夏毅然
冯圣玉
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Shandong University
Shandong Academy of Pharmaceutical Sciences
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Shandong University
Shandong Academy of Pharmaceutical Sciences
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/52—Amides or imides
    • C08F220/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L31/00—Materials for other surgical articles, e.g. stents, stent-grafts, shunts, surgical drapes, guide wires, materials for adhesion prevention, occluding devices, surgical gloves, tissue fixation devices
    • A61L31/04—Macromolecular materials
    • A61L31/048—Macromolecular materials obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L31/00—Materials for other surgical articles, e.g. stents, stent-grafts, shunts, surgical drapes, guide wires, materials for adhesion prevention, occluding devices, surgical gloves, tissue fixation devices
    • A61L31/14—Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L31/00—Materials for other surgical articles, e.g. stents, stent-grafts, shunts, surgical drapes, guide wires, materials for adhesion prevention, occluding devices, surgical gloves, tissue fixation devices
    • A61L31/14—Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
    • A61L31/18—Materials at least partially X-ray or laser opaque
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L2430/00—Materials or treatment for tissue regeneration
    • A61L2430/36—Materials or treatment for tissue regeneration for embolization or occlusion, e.g. vaso-occlusive compositions or devices

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  • Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Epidemiology (AREA)
  • Surgery (AREA)
  • Vascular Medicine (AREA)
  • Veterinary Medicine (AREA)
  • Chemical & Material Sciences (AREA)
  • Heart & Thoracic Surgery (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Physics & Mathematics (AREA)
  • Medicinal Chemistry (AREA)
  • Optics & Photonics (AREA)
  • Organic Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Materials For Medical Uses (AREA)

Abstract

The invention relates to the technical field of vessel embolus development materials in biomedical engineering, particularly a preparation method of an in-situ-gelation temperature-sensitive liquid embolic material capable of development for a long time. The preparation method comprises the following steps: carrying out recrystallization treatment on N-isopropyl acrylamide, and carrying out reaction on the recrystallized N-isopropyl acrylamide, butyl methacrylate and an iodine-containing monomer by adding an initiator and a crosslinking agent, thereby obtaining a temperature-sensitive copolymer; and repeatedly washing the temperature-sensitive copolymer in water, purifying, drying, dissolving the dried product in water for injection, and sterilizing, thereby obtaining the in-situ-gelation temperature-sensitive liquid embolic material. The development functional group is copolymerized with the isopropyl acrylamide and butyl methacrylate through the unsaturated monomer, and thus, the obtained polymer has the development characteristic. The iodine-containing part can not be lost due to the flow of the normal saline, body fluid and blood; and thus, the in-situ-gelation temperature-sensitive liquid embolic material performs the permanent embolism function, is a permanent-development embolic agent, can achieve the effect of long-term development, is convenient for reinspection, and reduces the economic burden of the patients.

Description

The preparation method of the long-term gelatinizing-in-situ responsive to temperature type liquid embolic material that develops
Technical field
The present invention relates to biomedical engineering blood vessel embolism developing material technical field, particularly to the preparation method of a kind of gelatinizing-in-situ responsive to temperature type liquid embolic material that self can develop for a long time。
Background technology
Transcatheter embolization is an important technology of interventional radiology。It is to utilize different types of conduit, and embolism materials has with controlling be injected in supply vessels or the pathological changes of pathological changes, so as to occur obturation interrupt blood confession, thus reach control hemorrhage, treat vascular lesions, treat tumor and eliminate the purpose of neuropathic organ。
The success or not of transcatheter embolization is played pivotal role by embolism materials。At present, the embolism materials having been used for clinic mostly adopts provisional additional developing agent, and such as tantalum powder class easily embeds not exclusively, and the non-ionic developing agent containing iodine is in the metabolism all at short notice of thromboembolism Post operation。During postoperative check, it is necessary to thromboembolism position carries out angiographic diagnosis again, and such Repeated Operation had both added injury when patient checks to health, too increased the surgery cost of patient。
Can having good market application foreground by developer liquids embolism materials, one is the demand of clinical operation, and two is have very big application group。The technical merit of China's interventional therapy, not second to developed country, is now just developed to small and medium-sized cities by big and medium-sized cities, popularizes, but, embolism materials 90% used relies on import, to expend a large amount of foreign exchange every year, owing to imported material is expensive, bring heavy financial burden to patient。It addition, the postoperative check of transcatheter embolization still needs to angiography, check number of times 1-4 time, each Operation Fee about 4000 yuan, the check expense for malignant tumor is about 4000-16000 unit。Develop excellent performance, cheap can developer liquids embolism materials, domestic clinical needs can be met, the level of China's interventional therapy can be improved again, patient's financial burden can be alleviated again, save foreign exchange, it is established that our national industry, there is important social benefit。
For these reasons, domestic and international research worker begins one's study and self has the liquid embolic material of developing function, material containing iodine is mainly combined with thromboembolism substrate by this kind of embolism materials with the form of covalent bond, make in embolism materials structure containing the material iodine that can develop, reach the double effects of thromboembolism development。This type of research major part is still in the synthetic test stage at present。
Current existing technological document application number is 200910020042.0 1 kinds of preparation methoies containing iodine liquid embolic agent capable of long-time self-developing, the method that this patent adopts is to add containing iodine compound after being dissolved by water-soluble poval (PVA), dichloromethane and triethylamine, dissolve with dimethyl sulfoxide or N-methyl-pyrrolidon after products therefrom Precipitation and be configured to suppository。And two other patent 200910014835.1 of this seminar can be developed containing iodine polymer and the preparation method containing iodine polymeric embolization material and a 201310438851.X endogenous development embolism materials of can developing, the method adopted is a kind of containing iodine unsaturated monomer for preparation, react with another kind of natural macromolecular material, the polymerizate obtained has developing property, development polymer is dissolved in organic solvent, development suppository can be obtained。
The standby suppository of three above patent system all adopts organic solvent such as oxolane, dimethyl sulfoxide, polymer is dissolved by N-methyl-pyrrolidon etc., and organic solvent is generally of vascular toxicity, corrosivity and causes the character of angionecrosis, it is easily caused feeding artery spasm and tunica intima infringement, it is possible to serious complication can be caused。
This seminar in the application number of application in 2014 is201410340324.X, name is calledResponsive to temperature type polymer and Gelatinizing-in-situ responsive to temperature type liquid embolic material and preparation method thereofThe first preparation temperature sensitive polymer of middle employing, responsive to temperature type polymer and developing agent are dissolved in water for injection or normal saline, are prepared into gelatinizing-in-situ responsive to temperature type embolism materials。Developing agent iohexol is dissolved in water, and when suppository enters focus and is precipitated out, major part developing agent can flow away with normal saline or body fluid, finally excretes, and observes so need to inject new developing agent during check；Add the injury to health when patient checks, too increase the surgery cost of patient。
Summary of the invention
The mixed type developing agent existed to solve above prior art is easy to run off, causes diagnosis cost high, there is the problem of potential safety hazard in response type developing agent, this application provides a kind of safe and reliable response type and develop for a long time the preparation method of gelatinizing-in-situ responsive to temperature type liquid embolic material。In position on the basis of gelation liquid embolic material, increase a kind of monomer containing iodine developed and be polymerized, when making thromboembolism and all visible under X-ray after thromboembolism, facilitate operation technique and postoperative check。
The present invention is achieved by the following measures:
A kind of preparation method of long-term development gelatinizing-in-situ responsive to temperature type liquid embolic material, it is characterized in that NIPA is carried out recrystallization process, take the NIPA after process, butyl methacrylate and containing iodine monomer, when condensing reflux in dioxane reacting by heating, and logical N2, add initiator and cross-linking agent reaction, obtain responsive to temperature type copolymer, by responsive to temperature type copolymer cyclic washing in water, purification, dry, the product after drying is dissolved in water for injection, sterilizing, to obtain final product。
Described preparation method, it is preferable that NIPA, butyl methacrylate and the mass ratio containing iodine monomer are 100:2-6:10-35, it is preferable that 100:2-4:25-35, more preferably 100:4:30。
Described preparation method, it is preferable that reaction temperature is 60 DEG C-85 DEG C, it is preferable that 75 DEG C。
Described preparation method, it is preferable that the response time is 2h-8h, it is preferable that 4-6h, it is preferable that 5h。
Described preparation method, it is preferable that cross-linking agent is N,N methylene bis acrylamide, dimethacrylate TEG ester, trimethylolpropane trimethacrylate, ethylene glycol bis acrylic ester or divinylbenzene。The mass ratio 100:0.5-5 of NIPA and cross-linking agent, it is preferable that 100:2。
The mass ratio 100:0.1-3 of described preparation method, it is preferable that initiator is azodiisobutyronitrile (AIBN), 2,2'-Azobis(2,4-dimethylvaleronitrile) (ABVN), azo-bis-iso-dimethyl etc., NIPA and initiator。
Described preparation method, it is preferable that the product after drying is dissolved in water for injection, the mass ratio of polymer and water for injection is 1-15:100。
Compared with the binary copolymerization of NIP and butyl methacrylate, the present invention adds the terpolymerization containing iodine monomer, and the product obtained still has temperature-sensing property, but due to the addition containing iodine monomer, add the content of hydrophobic group, cause that LCST decreases, phase in version time decreased。
Beneficial effects of the present invention:
1, development functional group is copolymerized with N-isopropylacrylamide and butyl methacrylate by unsaturated monomer, the polymer obtained itself has developing property, will not because of normal saline containing iodine part, the flowing of body fluid and blood and run off, play the effect of permanent thromboembolism, for the suppository of permanent development, it is possible to reach the effect of long-term development, both convenient check, alleviated again the financial burden of sufferer；
2, in formula for a product, solvent for use is water for injection or normal saline, non-stimulated, has no side effect, and has good biological safety, solution state, and concentration is low, good fluidity；
3, can develop polymeric liquid embolism materials, art is observed the flow direction and the effect of embolization of embolism materials by fluoroscopic monitoring, reduce the possibility of bolt by mistake in operation, postoperative retaining and effect of embolization by CT observation intralesional embolism materials, the problem solving postoperative check radiography, is beneficial to and follows up a case by regular visits to, succinctly facilitate, low cost is significant。
Detailed description of the invention
In order to be better understood from the present invention, further illustrate below in conjunction with specific embodiment。
Embodiment:
NIPA (NIP) is carried out recrystallization process, takes the NIP5g after process, butyl methacrylate, containing iodine monomer, when condensing reflux in dioxane reacting by heating, and logical N2, add initiator and cross-linking agent, react certain time, obtain terpolymer。
By responsive to temperature type copolymer cyclic washing in water, purification, dry；Product after drying is dissolved in water for injection according to a certain percentage, sterilizing, obtains gelatinizing-in-situ responsive to temperature type liquid embolic material。
In each embodiment, data are provided that
In table, iodine 1 is Triiodobenzoic acid acrylic ester, and iodine 2 is sodium iodide, and iodine 3 is Triiodobenzoic acid。
Handing over 1 is N,N methylene bis acrylamide, and handing over 2 is dimethacrylate TEG ester, and handing over 3 is trimethylolpropane trimethacrylate, and handing over 4 is ethylene glycol bis acrylic ester。
Initiator is azodiisobutyronitrile (AIBN), 2,2'-Azobis(2,4-dimethylvaleronitrile) (ABVN), azo-bis-iso-dimethyl etc., the mass ratio 100:0.1-3 of NIPA and initiator。
Stability
The embolism materials that above-described embodiment 3 prepares is configured to suppository according to finite concentration, it is placed in testing chamber for medicine stability and places 12 months, temperature 25 DEG C ± 2 DEG C, relative humidity 60% ± 10%, respectively at 0 month, 1 month, 3 months, 6 months, sampling in 12 months, project need to be investigated according to stability and investigate。
Stability test long-term investigation result:
Suppository concentration Visible foreign matters Phase transition temperature The phase in version time Content of iodine
0 month 5% Nothing 28.6℃ < 1min 27.1%
1 month 5% Nothing 28.6℃ < 1min 27.0%
3 months 5% Nothing 28.4℃ < 1min 27.2%
6 months 5% Nothing 28.5℃ < 1min 26.9%
12 months 5% Nothing 28.7℃ < 1min 27.0%
Above-described embodiment is the present invention preferably embodiment; but embodiments of the present invention also should not be limited by the examples; the change made under other any spirit without departing from the present invention and principle, modification, combination, replacement, simplification all should be equivalence substitute mode, are included within protection scope of the present invention。

Claims (10)

1. the preparation method of one kind long-term development gelatinizing-in-situ responsive to temperature type liquid embolic material, it is characterized in that NIPA is carried out recrystallization process, take the NIPA after process, butyl methacrylate and containing iodine monomer, when condensing reflux in dioxane reacting by heating, and logical N2, add initiator and cross-linking agent reaction, obtain responsive to temperature type copolymer, by responsive to temperature type copolymer cyclic washing in water, purification, dry, the product after drying is dissolved in water for injection, sterilizing, to obtain final product。
2. preparation method according to claim 1, it is characterised in that NIPA, butyl methacrylate and the mass ratio containing iodine monomer are 100:2-6:10-35。
3. preparation method according to claim 1, it is characterised in that be Triiodobenzoic acid acrylic ester, sodium iodide or Triiodobenzoic acid containing iodine monomer。
4. preparation method according to claim 1, it is characterised in that reaction temperature is 60 DEG C-85 DEG C。
5. preparation method according to claim 1, it is characterised in that response time 2h-8h。
6. preparation method according to claim 1, it is characterised in that cross-linking agent is N,N methylene bis acrylamide, dimethacrylate TEG ester, double; two acrylimide, trimethylolpropane trimethacrylate, ethylene glycol bis acrylic ester or divinylbenzene。
7. preparation method according to claim 1, it is characterised in that the mass ratio 100:0.5-5 of NIPA and cross-linking agent。
8. preparation method according to claim 1, it is characterised in that initiator is azodiisobutyronitrile, 2,2'-Azobis(2,4-dimethylvaleronitrile) or azo-bis-iso-dimethyl。
9. preparation method according to claim 1, it is characterised in that the mass ratio of NIPA and initiator is 100:0.1-3。
10. preparation method according to claim 1, it is characterised in that the product after drying is dissolved in water for injection, and the mass ratio of water for injection is 1-15:100。
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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018040407A1 (en) * 2016-08-31 2018-03-08 安疗生命科学（武汉）有限公司 Embolism material for blood vessel, preparation method therefor and use thereof in preparation of drugs
CN110819161A (en) * 2019-11-18 2020-02-21 南京森工生物科技有限公司 Printable developing ink and preparation method thereof
CN113651906A (en) * 2020-05-12 2021-11-16 上海盛迪医药有限公司 Copolymer and composition thereof

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101544701A (en) * 2009-04-28 2009-09-30 山东省医疗器械研究所 Developable iodic polymer and embolic material thereof
CN103483501A (en) * 2013-09-25 2014-01-01 山东省医疗器械研究所 Preparation method for endogenous developing embolization material
CN104130348A (en) * 2014-07-17 2014-11-05 山东省医疗器械研究所 Temperature-sensitive polymer, in-situ gelation temperature-sensitive liquid embolic material and preparation method thereof

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101544701A (en) * 2009-04-28 2009-09-30 山东省医疗器械研究所 Developable iodic polymer and embolic material thereof
CN103483501A (en) * 2013-09-25 2014-01-01 山东省医疗器械研究所 Preparation method for endogenous developing embolization material
CN104130348A (en) * 2014-07-17 2014-11-05 山东省医疗器械研究所 Temperature-sensitive polymer, in-situ gelation temperature-sensitive liquid embolic material and preparation method thereof

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018040407A1 (en) * 2016-08-31 2018-03-08 安疗生命科学（武汉）有限公司 Embolism material for blood vessel, preparation method therefor and use thereof in preparation of drugs
US11291748B2 (en) 2016-08-31 2022-04-05 Anew-Med Life Science (Wuhan) Co., Ltd Embolism material for blood vessel, preparation method therefor and use thereof in preparation of drugs
CN110819161A (en) * 2019-11-18 2020-02-21 南京森工生物科技有限公司 Printable developing ink and preparation method thereof
CN113651906A (en) * 2020-05-12 2021-11-16 上海盛迪医药有限公司 Copolymer and composition thereof
CN113651906B (en) * 2020-05-12 2024-02-20 上海盛迪医药有限公司 Copolymer and composition thereof

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