CA2877096A1 - Heat-sensitive amphiphilic polyurethane and aqueous solution capable of being injected based on such material - Google Patents

Heat-sensitive amphiphilic polyurethane and aqueous solution capable of being injected based on such material Download PDF

Info

Publication number: CA2877096A1
Authority: CA; Canada
Prior art keywords: composition according; amount; solution; polyurethane; diisocyanate
Prior art date: 2012-07-27
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Abandoned

Application number

CA2877096A

Other languages

English (en)

French (fr)

Inventor

Gianluca Ciardelli

Susanna SARTORI

Monica BOFFITO

Piero SERAFINI

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

GELTIS Srl

Original Assignee

GELTIS Srl

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2012-07-27

Filing date

2013-07-11

Publication date

2014-01-30

2013-07-11 Application filed by GELTIS Srl filed Critical GELTIS Srl

2014-01-30 Publication of CA2877096A1 publication Critical patent/CA2877096A1/en

Status Abandoned legal-status Critical Current

Links

239000004814 polyurethane Substances 0.000 title claims abstract description 51
229920002635 polyurethane Polymers 0.000 title claims abstract description 50
239000007864 aqueous solution Substances 0.000 title claims abstract description 7
239000000463 material Substances 0.000 title description 8
239000000203 mixture Substances 0.000 claims abstract description 59
239000000243 solution Substances 0.000 claims description 34
229920000642 polymer Polymers 0.000 claims description 24
125000005442 diisocyanate group Chemical group 0.000 claims description 19
239000003814 drug Substances 0.000 claims description 18
239000002904 solvent Substances 0.000 claims description 18
239000004970 Chain extender Substances 0.000 claims description 17
239000011541 reaction mixture Substances 0.000 claims description 15
239000002202 Polyethylene glycol Substances 0.000 claims description 14
229920001223 polyethylene glycol Polymers 0.000 claims description 14
229940079593 drug Drugs 0.000 claims description 13
VOXZDWNPVJITMN-ZBRFXRBCSA-N 17β-estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 VOXZDWNPVJITMN-ZBRFXRBCSA-N 0.000 claims description 10
150000004985 diamines Chemical class 0.000 claims description 10
229920000159 gelatin Polymers 0.000 claims description 8
235000019322 gelatine Nutrition 0.000 claims description 8
239000001828 Gelatine Substances 0.000 claims description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
-1 cyclic diols Chemical class 0.000 claims description 6
229920005615 natural polymer Polymers 0.000 claims description 6
238000006116 polymerization reaction Methods 0.000 claims description 6
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 5
150000002009 diols Chemical class 0.000 claims description 5
108090000623 proteins and genes Proteins 0.000 claims description 5
102000004169 proteins and genes Human genes 0.000 claims description 5
230000002441 reversible effect Effects 0.000 claims description 5
239000003054 catalyst Substances 0.000 claims description 4
239000000945 filler Substances 0.000 claims description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 3
125000003275 alpha amino acid group Chemical group 0.000 claims description 3
230000000975 bioactive effect Effects 0.000 claims description 3
150000001720 carbohydrates Chemical class 0.000 claims description 3
235000014633 carbohydrates Nutrition 0.000 claims description 3
125000000524 functional group Chemical group 0.000 claims description 3
239000003102 growth factor Substances 0.000 claims description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
LCPNYLRZLNERIG-ZETCQYMHSA-N (2S)-6-amino-2-[2-(oxomethylidene)hydrazinyl]hexanoyl isocyanate Chemical compound NCCCC[C@H](NN=C=O)C(=O)N=C=O LCPNYLRZLNERIG-ZETCQYMHSA-N 0.000 claims description 2
102000008186 Collagen Human genes 0.000 claims description 2
108010035532 Collagen Proteins 0.000 claims description 2
239000002253 acid Substances 0.000 claims description 2
125000001931 aliphatic group Chemical group 0.000 claims description 2
150000003862 amino acid derivatives Chemical class 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
229920001436 collagen Polymers 0.000 claims description 2
150000001875 compounds Chemical class 0.000 claims description 2
YMWUJEATGCHHMB-UHFFFAOYSA-N dichloromethane Substances ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 2
150000003512 tertiary amines Chemical class 0.000 claims description 2
230000017423 tissue regeneration Effects 0.000 claims description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims 1
239000012153 distilled water Substances 0.000 claims 1
239000007972 injectable composition Substances 0.000 claims 1
239000007791 liquid phase Substances 0.000 claims 1
239000000499 gel Substances 0.000 description 44
230000015572 biosynthetic process Effects 0.000 description 18
238000003786 synthesis reaction Methods 0.000 description 16
239000000017 hydrogel Substances 0.000 description 15
238000000034 method Methods 0.000 description 15
230000007704 transition Effects 0.000 description 14
239000003153 chemical reaction reagent Substances 0.000 description 9
230000008569 process Effects 0.000 description 9
210000001519 tissue Anatomy 0.000 description 9
238000012360 testing method Methods 0.000 description 8
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
238000001727 in vivo Methods 0.000 description 6
230000003993 interaction Effects 0.000 description 6
230000001172 regenerating effect Effects 0.000 description 6
238000004458 analytical method Methods 0.000 description 5
210000004027 cell Anatomy 0.000 description 5
239000000693 micelle Substances 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 description 4
238000013270 controlled release Methods 0.000 description 4
230000002209 hydrophobic effect Effects 0.000 description 4
239000000178 monomer Substances 0.000 description 4
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
230000001419 dependent effect Effects 0.000 description 3
238000009472 formulation Methods 0.000 description 3
239000001257 hydrogen Substances 0.000 description 3
229910052739 hydrogen Inorganic materials 0.000 description 3
238000002347 injection Methods 0.000 description 3
239000007924 injection Substances 0.000 description 3
238000003780 insertion Methods 0.000 description 3
230000037431 insertion Effects 0.000 description 3
239000007788 liquid Substances 0.000 description 3
229920005862 polyol Polymers 0.000 description 3
150000003077 polyols Chemical class 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
235000018102 proteins Nutrition 0.000 description 3
239000000126 substance Substances 0.000 description 3
JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 3
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
239000002126 C01EB10 - Adenosine Substances 0.000 description 2
238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 2
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
DEFJQIDDEAULHB-IMJSIDKUSA-N L-alanyl-L-alanine Chemical group C[C@H](N)C(=O)N[C@@H](C)C(O)=O DEFJQIDDEAULHB-IMJSIDKUSA-N 0.000 description 2
UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 2
229960005305 adenosine Drugs 0.000 description 2
230000002776 aggregation Effects 0.000 description 2
238000004220 aggregation Methods 0.000 description 2
239000012736 aqueous medium Substances 0.000 description 2
108010072041 arginyl-glycyl-aspartic acid Proteins 0.000 description 2
239000012298 atmosphere Substances 0.000 description 2
230000006378 damage Effects 0.000 description 2
239000012975 dibutyltin dilaurate Substances 0.000 description 2
230000002255 enzymatic effect Effects 0.000 description 2
238000001879 gelation Methods 0.000 description 2
125000001165 hydrophobic group Chemical group 0.000 description 2
239000007943 implant Substances 0.000 description 2
239000002808 molecular sieve Substances 0.000 description 2
210000000056 organ Anatomy 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
229920003226 polyurethane urea Polymers 0.000 description 2
238000001556 precipitation Methods 0.000 description 2
108090000765 processed proteins & peptides Proteins 0.000 description 2
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 2
238000001356 surgical procedure Methods 0.000 description 2
JHBKBRLRYPYBLP-UHFFFAOYSA-N tert-butyl n-(1,3-dihydroxypropan-2-yl)carbamate Chemical compound CC(C)(C)OC(=O)NC(CO)CO JHBKBRLRYPYBLP-UHFFFAOYSA-N 0.000 description 2
231100000331 toxic Toxicity 0.000 description 2
230000002588 toxic effect Effects 0.000 description 2
IYMAXBFPHPZYIK-BQBZGAKWSA-N Arg-Gly-Asp Chemical compound NC(N)=NCCC[C@H](N)C(=O)NCC(=O)N[C@@H](CC(O)=O)C(O)=O IYMAXBFPHPZYIK-BQBZGAKWSA-N 0.000 description 1
102000020313 Cell-Penetrating Peptides Human genes 0.000 description 1
108010051109 Cell-Penetrating Peptides Proteins 0.000 description 1
108010037362 Extracellular Matrix Proteins Proteins 0.000 description 1
102000010834 Extracellular Matrix Proteins Human genes 0.000 description 1
239000004606 Fillers/Extenders Substances 0.000 description 1
238000001157 Fourier transform infrared spectrum Methods 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
239000004472 Lysine Substances 0.000 description 1
229920001730 Moisture cure polyurethane Polymers 0.000 description 1
239000004721 Polyphenylene oxide Substances 0.000 description 1
108091006629 SLC13A2 Proteins 0.000 description 1
238000005411 Van der Waals force Methods 0.000 description 1
239000000654 additive Substances 0.000 description 1
108010056243 alanylalanine Proteins 0.000 description 1
239000003125 aqueous solvent Substances 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
210000000988 bone and bone Anatomy 0.000 description 1
210000000845 cartilage Anatomy 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
230000008859 change Effects 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000002537 cosmetic Substances 0.000 description 1
XHMWGEWUBYMZDB-UHFFFAOYSA-N cyclooctane-1,1-diamine Chemical compound NC1(N)CCCCCCC1 XHMWGEWUBYMZDB-UHFFFAOYSA-N 0.000 description 1
230000007423 decrease Effects 0.000 description 1
230000007547 defect Effects 0.000 description 1
230000000593 degrading effect Effects 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
238000004821 distillation Methods 0.000 description 1
230000002500 effect on skin Effects 0.000 description 1
230000000694 effects Effects 0.000 description 1
230000007613 environmental effect Effects 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
238000002270 exclusion chromatography Methods 0.000 description 1
210000002744 extracellular matrix Anatomy 0.000 description 1
238000011049 filling Methods 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
239000008103 glucose Substances 0.000 description 1
150000004676 glycans Chemical class 0.000 description 1
230000035876 healing Effects 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
230000001939 inductive effect Effects 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
230000002427 irreversible effect Effects 0.000 description 1
IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
230000000670 limiting effect Effects 0.000 description 1
230000005923 long-lasting effect Effects 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
239000002609 medium Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
150000002902 organometallic compounds Chemical class 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
238000004806 packaging method and process Methods 0.000 description 1
239000008363 phosphate buffer Substances 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920000747 poly(lactic acid) Polymers 0.000 description 1
229920001282 polysaccharide Polymers 0.000 description 1
239000005017 polysaccharide Substances 0.000 description 1
239000000843 powder Substances 0.000 description 1
102000004196 processed proteins & peptides Human genes 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
238000000746 purification Methods 0.000 description 1
230000002829 reductive effect Effects 0.000 description 1
230000008929 regeneration Effects 0.000 description 1
238000011069 regeneration method Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000007787 solid Substances 0.000 description 1
230000007928 solubilization Effects 0.000 description 1
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238000003860 storage Methods 0.000 description 1
239000000758 substrate Substances 0.000 description 1
229920001059 synthetic polymer Polymers 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
230000010512 thermal transition Effects 0.000 description 1
230000036962 time dependent Effects 0.000 description 1
238000012546 transfer Methods 0.000 description 1

Classifications

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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- A61K47/34—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyesters, polyamino acids, polysiloxanes, polyphosphazines, copolymers of polyalkylene glycol or poloxamers
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- A61L27/50—Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
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- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/73—Polyisocyanates or polyisothiocyanates acyclic
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G18/72—Polyisocyanates or polyisothiocyanates
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- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
- C08G18/7664—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups
- C08G18/7671—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups containing only one alkylene bisphenyl group
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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- 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
- A61L2400/00—Materials characterised by their function or physical properties
- A61L2400/06—Flowable or injectable implant compositions
- 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
- A61L2430/02—Materials or treatment for tissue regeneration for reconstruction of bones; weight-bearing implants
- 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
- A61L2430/20—Materials or treatment for tissue regeneration for reconstruction of the heart, e.g. heart valves
- 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
- A61L2430/34—Materials or treatment for tissue regeneration for soft tissue reconstruction

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Epidemiology (AREA)
Dermatology (AREA)
Transplantation (AREA)
Oral & Maxillofacial Surgery (AREA)
Pharmacology & Pharmacy (AREA)
Dispersion Chemistry (AREA)
Inorganic Chemistry (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Neurosurgery (AREA)
Biomedical Technology (AREA)
Engineering & Computer Science (AREA)
Materials For Medical Uses (AREA)
Medicinal Preparation (AREA)
Polyurethanes Or Polyureas (AREA)
Compositions Of Macromolecular Compounds (AREA)
Thermotherapy And Cooling Therapy Devices (AREA)
Cosmetics (AREA)

CA2877096A 2012-07-27 2013-07-11 Heat-sensitive amphiphilic polyurethane and aqueous solution capable of being injected based on such material Abandoned CA2877096A1 (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
IT000669A ITTO20120669A1 (it)	2012-07-27	2012-07-27	Poliuretani anfifilici termosensibili e soluzione acquosa iniettabile a base di tale materiale.
ITTO2012A000669		2012-07-27
PCT/IT2013/000196 WO2014016857A1 (en)	2012-07-27	2013-07-11	Heat-sensitive amphiphilic polyurethane and aqueous solution capable of being injected based on such material

Publications (1)

Publication Number	Publication Date
CA2877096A1 true CA2877096A1 (en)	2014-01-30

Family

ID=46982769

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA2877096A Abandoned CA2877096A1 (en)	2012-07-27	2013-07-11	Heat-sensitive amphiphilic polyurethane and aqueous solution capable of being injected based on such material

Country Status (13)

Country	Link
US (1)	US20150250889A1 (2)
EP (1)	EP2877514A1 (2)
JP (1)	JP2015524864A (2)
KR (1)	KR20150037873A (2)
CN (1)	CN104507994A (2)
BR (1)	BR112015001635A2 (2)
CA (1)	CA2877096A1 (2)
CL (1)	CL2015000195A1 (2)
IN (1)	IN2015KN00016A (2)
IT (1)	ITTO20120669A1 (2)
MX (1)	MX2015001035A (2)
RU (1)	RU2015106123A (2)
WO (1)	WO2014016857A1 (2)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN110724245A (zh) *	2018-07-17	2020-01-24	四川大学	可注射的聚氨酯及其制备方法
WO2020209740A1 (en)	2019-04-12	2020-10-15	Institutul De Chimie Macromoleculară Petru Poni	Non-isocyanate polyurethane thermoreversible hydrogel and method for its preparation

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4822827A (en)	1987-12-17	1989-04-18	The Dow Chemical Company	Thermoplastic polyurethanes with high glass transition temperatures
US5000955A (en) *	1988-07-29	1991-03-19	Tyndale Plains-Hunter Ltd.	Thermally reversible polyurethane hydrogels and cosmetic, biological and medical uses
US5254662A (en)	1990-09-12	1993-10-19	Polymedia Industries, Inc.	Biostable polyurethane products
JPH08507715A (ja)	1993-03-18	1996-08-20	シーダーズサイナイメディカルセンター	生体人工部材のための薬剤導入性および放出性重合性コーティング
TW200604249A (en)	2004-03-24	2006-02-01	Commw Scient Ind Res Org	Biodegradable polyurethane and polyurethane ureas
WO2007117222A1 (en) *	2006-04-12	2007-10-18	Agency For Science, Technology And Research	Biodegradable thermogelling polymer
US20120089491A1 (en) *	2008-07-02	2012-04-12	Katia Weber	System and method of providing enhanced transaction data

2012
- 2012-07-27 IT IT000669A patent/ITTO20120669A1/it unknown
2013
- 2013-07-11 EP EP13756713.7A patent/EP2877514A1/en not_active Withdrawn
- 2013-07-11 IN IN16KON2015 patent/IN2015KN00016A/en unknown
- 2013-07-11 BR BR112015001635A patent/BR112015001635A2/pt not_active IP Right Cessation
- 2013-07-11 RU RU2015106123A patent/RU2015106123A/ru not_active Application Discontinuation
- 2013-07-11 KR KR20157001768A patent/KR20150037873A/ko not_active Withdrawn
- 2013-07-11 CA CA2877096A patent/CA2877096A1/en not_active Abandoned
- 2013-07-11 US US14/417,736 patent/US20150250889A1/en not_active Abandoned
- 2013-07-11 MX MX2015001035A patent/MX2015001035A/es unknown
- 2013-07-11 JP JP2015523661A patent/JP2015524864A/ja not_active Abandoned
- 2013-07-11 CN CN201380038838.3A patent/CN104507994A/zh active Pending
- 2013-07-11 WO PCT/IT2013/000196 patent/WO2014016857A1/en not_active Ceased
2015
- 2015-01-26 CL CL2015000195A patent/CL2015000195A1/es unknown

Also Published As

Publication number	Publication date
IN2015KN00016A (2)	2015-07-31
WO2014016857A1 (en)	2014-01-30
MX2015001035A (es)	2015-06-23
EP2877514A1 (en)	2015-06-03
RU2015106123A (ru)	2016-09-20
US20150250889A1 (en)	2015-09-10
CL2015000195A1 (es)	2015-05-08
KR20150037873A (ko)	2015-04-08
BR112015001635A2 (pt)	2017-07-04
JP2015524864A (ja)	2015-08-27
CN104507994A (zh)	2015-04-08
ITTO20120669A1 (it)	2012-10-26

Legal Events

Date	Code	Title	Description
2018-08-22	FZDE	Discontinued	Effective date: 20180711

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