CA1260488A - Preparation de cire homeostatique absorbable - Google Patents

Preparation de cire homeostatique absorbable

Info

Publication number: CA1260488A
Authority: CA; Canada
Prior art keywords: glycolide; castor oil; process according; fatty acid; catalyst
Prior art date: 1986-07-07
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.): Expired

Application number

CA000513258A

Other languages

English (en)

Inventor

Alexander M. Henderson

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.)

Johnson and Johnson Medical Ltd

Original Assignee

Ethicon Ltd

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.)

1986-07-07

Filing date

1986-07-07

Publication date

1989-09-26

1986-07-07 Application filed by Ethicon Ltd filed Critical Ethicon Ltd

1986-07-07 Priority to CA000513258A priority Critical patent/CA1260488A/fr

1989-09-26 Application granted granted Critical

1989-09-26 Publication of CA1260488A publication Critical patent/CA1260488A/fr

Status Expired legal-status Critical Current

Links

239000000203 mixture Substances 0.000 title claims abstract description 48
210000000988 bone and bone Anatomy 0.000 title claims description 31
238000009472 formulation Methods 0.000 title description 10
RKDVKSZUMVYZHH-UHFFFAOYSA-N 1,4-dioxane-2,5-dione Chemical compound O=C1COC(=O)CO1 RKDVKSZUMVYZHH-UHFFFAOYSA-N 0.000 claims abstract description 72
239000004359 castor oil Substances 0.000 claims abstract description 62
235000019438 castor oil Nutrition 0.000 claims abstract description 61
ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 claims abstract description 61
239000007787 solid Substances 0.000 claims abstract description 41
JJTUDXZGHPGLLC-UHFFFAOYSA-N lactide Chemical compound CC1OC(=O)C(C)OC1=O JJTUDXZGHPGLLC-UHFFFAOYSA-N 0.000 claims abstract description 20
229920001634 Copolyester Polymers 0.000 claims abstract description 17
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 16
229920005989 resin Polymers 0.000 claims abstract description 15
239000011347 resin Substances 0.000 claims abstract description 15
150000002596 lactones Chemical class 0.000 claims abstract description 12
208000032843 Hemorrhage Diseases 0.000 claims abstract description 10
229920002307 Dextran Polymers 0.000 claims abstract description 7
239000003054 catalyst Substances 0.000 claims description 31
238000006243 chemical reaction Methods 0.000 claims description 25
235000014113 dietary fatty acids Nutrition 0.000 claims description 14
229930195729 fatty acid Natural products 0.000 claims description 14
239000000194 fatty acid Substances 0.000 claims description 14
-1 fatty acid salt Chemical class 0.000 claims description 14
238000000034 method Methods 0.000 claims description 14
KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 claims description 13
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
229910052757 nitrogen Inorganic materials 0.000 claims description 4
238000006116 polymerization reaction Methods 0.000 claims description 4
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical group [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 3
229910052791 calcium Inorganic materials 0.000 claims description 3
239000011575 calcium Substances 0.000 claims description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 3
150000001768 cations Chemical class 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
229920006395 saturated elastomer Polymers 0.000 claims description 3
239000012298 atmosphere Substances 0.000 claims description 2
239000000376 reactant Substances 0.000 claims description 2
239000000565 sealant Substances 0.000 claims description 2
239000001993 wax Substances 0.000 abstract description 40
239000003921 oil Substances 0.000 abstract description 20
CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 abstract description 9
235000013539 calcium stearate Nutrition 0.000 abstract description 8
239000008116 calcium stearate Substances 0.000 abstract description 8
229940030225 antihemorrhagics Drugs 0.000 abstract description 3
239000000155 melt Substances 0.000 abstract description 3
239000000843 powder Substances 0.000 abstract description 2
UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 34
239000000047 product Substances 0.000 description 32
238000003756 stirring Methods 0.000 description 13
239000000463 material Substances 0.000 description 12
229920000728 polyester Polymers 0.000 description 12
239000003708 ampul Substances 0.000 description 9
238000001727 in vivo Methods 0.000 description 8
JJTUDXZGHPGLLC-IMJSIDKUSA-N 4511-42-6 Chemical compound C[C@@H]1OC(=O)[C@H](C)OC1=O JJTUDXZGHPGLLC-IMJSIDKUSA-N 0.000 description 7
241000700159 Rattus Species 0.000 description 6
238000010521 absorption reaction Methods 0.000 description 6
238000004458 analytical method Methods 0.000 description 6
239000002245 particle Substances 0.000 description 6
239000007788 liquid Substances 0.000 description 5
229920000642 polymer Polymers 0.000 description 5
229920001577 copolymer Polymers 0.000 description 4
239000006185 dispersion Substances 0.000 description 4
LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 4
239000011521 glass Substances 0.000 description 4
238000004811 liquid chromatography Methods 0.000 description 4
239000004570 mortar (masonry) Substances 0.000 description 4
229920003023 plastic Polymers 0.000 description 4
239000004033 plastic Substances 0.000 description 4
238000007711 solidification Methods 0.000 description 4
230000008023 solidification Effects 0.000 description 4
210000001519 tissue Anatomy 0.000 description 4
241001465754 Metazoa Species 0.000 description 3
239000000084 colloidal system Substances 0.000 description 3
238000001816 cooling Methods 0.000 description 3
239000012530 fluid Substances 0.000 description 3
238000005194 fractionation Methods 0.000 description 3
230000002209 hydrophobic effect Effects 0.000 description 3
238000002156 mixing Methods 0.000 description 3
239000002904 solvent Substances 0.000 description 3
235000019222 white chocolate Nutrition 0.000 description 3
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Polymers OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
230000000740 bleeding effect Effects 0.000 description 2
WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
230000023597 hemostasis Effects 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
238000005259 measurement Methods 0.000 description 2
210000003205 muscle Anatomy 0.000 description 2
230000005855 radiation Effects 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
230000003655 tactile properties Effects 0.000 description 2
BYEAHWXPCBROCE-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound FC(F)(F)C(O)C(F)(F)F BYEAHWXPCBROCE-UHFFFAOYSA-N 0.000 description 1
206010002091 Anaesthesia Diseases 0.000 description 1
206010053567 Coagulopathies Diseases 0.000 description 1
206010061218 Inflammation Diseases 0.000 description 1
241000906034 Orthops Species 0.000 description 1
241000283216 Phocidae Species 0.000 description 1
229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
229920000954 Polyglycolide Polymers 0.000 description 1
239000004793 Polystyrene Substances 0.000 description 1
239000004830 Super Glue Substances 0.000 description 1
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
108090000190 Thrombin Proteins 0.000 description 1
238000001949 anaesthesia Methods 0.000 description 1
230000037005 anaesthesia Effects 0.000 description 1
238000010171 animal model Methods 0.000 description 1
235000013871 bee wax Nutrition 0.000 description 1
239000012166 beeswax Substances 0.000 description 1
238000005452 bending Methods 0.000 description 1
239000000560 biocompatible material Substances 0.000 description 1
210000001124 body fluid Anatomy 0.000 description 1
239000010839 body fluid Substances 0.000 description 1
235000014121 butter Nutrition 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
230000001413 cellular effect Effects 0.000 description 1
238000012512 characterization method Methods 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
229940112822 chewing gum Drugs 0.000 description 1
235000015218 chewing gum Nutrition 0.000 description 1
230000035602 clotting Effects 0.000 description 1
DEZRYPDIMOWBDS-UHFFFAOYSA-N dcm dichloromethane Chemical compound ClCCl.ClCCl DEZRYPDIMOWBDS-UHFFFAOYSA-N 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000010828 elution Methods 0.000 description 1
230000002708 enhancing effect Effects 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
230000007717 exclusion Effects 0.000 description 1
230000001747 exhibiting effect Effects 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
239000000945 filler Substances 0.000 description 1
239000012467 final product Substances 0.000 description 1
235000013305 food Nutrition 0.000 description 1
150000002314 glycerols Chemical class 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
230000035876 healing Effects 0.000 description 1
235000012907 honey Nutrition 0.000 description 1
239000007943 implant Substances 0.000 description 1
238000002513 implantation Methods 0.000 description 1
230000008595 infiltration Effects 0.000 description 1
238000001764 infiltration Methods 0.000 description 1
230000004054 inflammatory process Effects 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
230000017074 necrotic cell death Effects 0.000 description 1
231100000989 no adverse effect Toxicity 0.000 description 1
229920002463 poly(p-dioxanone) polymer Polymers 0.000 description 1
239000000622 polydioxanone Substances 0.000 description 1
229920001225 polyester resin Polymers 0.000 description 1
239000004645 polyester resin Substances 0.000 description 1
239000002685 polymerization catalyst Substances 0.000 description 1
229920005862 polyol Polymers 0.000 description 1
150000003077 polyols Chemical class 0.000 description 1
229920002223 polystyrene Polymers 0.000 description 1
HJHVQCXHVMGZNC-JCJNLNMISA-M sodium;(2z)-2-[(3r,4s,5s,8s,9s,10s,11r,13r,14s,16s)-16-acetyloxy-3,11-dihydroxy-4,8,10,14-tetramethyl-2,3,4,5,6,7,9,11,12,13,15,16-dodecahydro-1h-cyclopenta[a]phenanthren-17-ylidene]-6-methylhept-5-enoate Chemical compound [Na+].O[C@@H]([C@@H]12)C[C@H]3\C(=C(/CCC=C(C)C)C([O-])=O)[C@@H](OC(C)=O)C[C@]3(C)[C@@]2(C)CC[C@@H]2[C@]1(C)CC[C@@H](O)[C@H]2C HJHVQCXHVMGZNC-JCJNLNMISA-M 0.000 description 1
239000007858 starting material Substances 0.000 description 1
230000001954 sterilising effect Effects 0.000 description 1
238000004659 sterilization and disinfection Methods 0.000 description 1
238000001356 surgical procedure Methods 0.000 description 1
229960004072 thrombin Drugs 0.000 description 1
229940045860 white wax Drugs 0.000 description 1

Classifications

- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/78—Preparation processes
- C08G63/82—Preparation processes characterised by the catalyst used
- C08G63/823—Preparation processes characterised by the catalyst used for the preparation of polylactones or polylactides
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/74—Synthetic polymeric materials
- A61K31/765—Polymers containing oxygen
- 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
- A61L24/00—Surgical adhesives or cements; Adhesives for colostomy devices
- A61L24/04—Surgical adhesives or cements; Adhesives for colostomy devices containing macromolecular materials
- A61L24/046—Surgical adhesives or cements; Adhesives for colostomy devices containing macromolecular materials obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/06—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from hydroxycarboxylic acids
- C08G63/08—Lactones or lactides

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Organic Chemistry (AREA)
Epidemiology (AREA)
Life Sciences & Earth Sciences (AREA)
Polymers & Plastics (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Surgery (AREA)
Polyesters Or Polycarbonates (AREA)

CA000513258A 1986-07-07 1986-07-07 Preparation de cire homeostatique absorbable Expired CA1260488A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000513258A CA1260488A (fr)	1986-07-07	1986-07-07	Preparation de cire homeostatique absorbable

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA000513258A CA1260488A (fr)	1986-07-07	1986-07-07	Preparation de cire homeostatique absorbable

Publications (1)

Publication Number	Publication Date
CA1260488A true CA1260488A (fr)	1989-09-26

Family

ID=4133512

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000513258A Expired CA1260488A (fr)	1986-07-07	1986-07-07	Preparation de cire homeostatique absorbable

Country Status (1)

Country	Link
CA (1)	CA1260488A (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5371176A (en) *	1993-02-05	1994-12-06	Ethicon, Inc.	Castor oil polymers
US5681873A (en) *	1993-10-14	1997-10-28	Atrix Laboratories, Inc.	Biodegradable polymeric composition
US6261583B1 (en)	1998-07-28	2001-07-17	Atrix Laboratories, Inc.	Moldable solid delivery system
WO2005095378A3 (fr) *	2004-03-24	2006-03-16	Archer Daniels Midland Co	Derives de dioxanone utilisant des legumes, leurs syntheses et leurs utilisations
WO2008029527A1 (fr)	2006-09-04	2008-03-13	Bio-Energy Corporation	Polyol de polyester

1986
- 1986-07-07 CA CA000513258A patent/CA1260488A/fr not_active Expired

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5371176A (en) *	1993-02-05	1994-12-06	Ethicon, Inc.	Castor oil polymers
EP0610086A3 (fr) *	1993-02-05	1994-12-21	Ethicon Inc	Polymères d'huile de rinein pour revêtements d'aiguille.
US5681873A (en) *	1993-10-14	1997-10-28	Atrix Laboratories, Inc.	Biodegradable polymeric composition
US6261583B1 (en)	1998-07-28	2001-07-17	Atrix Laboratories, Inc.	Moldable solid delivery system
WO2005095378A3 (fr) *	2004-03-24	2006-03-16	Archer Daniels Midland Co	Derives de dioxanone utilisant des legumes, leurs syntheses et leurs utilisations
US7754823B2 (en)	2004-03-24	2010-07-13	Archer-Daniels-Midland Company	Vegetable based dioxanone derivatives, synthesis and uses thereof
WO2008029527A1 (fr)	2006-09-04	2008-03-13	Bio-Energy Corporation	Polyol de polyester
EP2065421A4 (fr) *	2006-09-04	2010-12-15	Bio Energy Corp	Polyol de polyester
US8058470B2 (en)	2006-09-04	2011-11-15	Bio-Energy Corporation	Polyester polyol

Legal Events

Date	Code	Title	Description
2006-09-26	MKEX	Expiry

Publication	Publication Date	Title
US4440789A (en)	1984-04-03	Synthetic absorbable hemostatic composition
US4439420A (en)	1984-03-27	Absorbable hemostatic composition
DE69617277T2 (de)	2002-05-23	Absorbierbare Polyalkylendiglycolate
US4443430A (en)	1984-04-17	Synthetic absorbable hemostatic agent
EP1010436B1 (fr)	2002-10-16	Cire osseuse
CA2175285C (fr)	2006-07-11	Materiel chirurgical moulable biodegradable
JP2774824B2 (ja)	1998-07-09	吸収性骨蝋
US4595713A (en)	1986-06-17	Medical putty for tissue augmentation
AU2001279839B2 (en)	2007-05-31	Biologically active material
US5725881A (en)	1998-03-10	Semisolid mixtures of amorphous oligomers and crystalline polymers based on lactic acid
AU741741B2 (en)	2001-12-06	Polyesterhydrogels
IE47606B1 (en)	1984-05-02	Absorbable hemostatic composition
EP0399827A3 (fr)	1991-08-07	Composition de polyester modifiée, son procédé de préparation et son utilisation
DE3826915A1 (de)	1990-02-15	Neue werkstoffe fuer den knochenersatz und knochen- bzw. prothesenverbund
AU2001279839A1 (en)	2002-05-02	Biologically active material
EP0994736B1 (fr)	2003-05-28	Nouveau composite a base plastique et utilisation de ce composite
KR102390186B1 (ko)	2022-04-22	화장품용 생분해성 공중합체
CA1260488A (fr)	1989-09-26	Preparation de cire homeostatique absorbable
WO1986001113A1 (fr)	1986-02-27	Materiau de remplacement d'os
EP0100981B1 (fr)	1989-01-18	Cires osseuses biorésorbables
USRE32208E (en)	1986-07-15	Absorbable hemostatic composition
JP2002505359A (ja)	2002-02-19	天然に生じる再生可能な原材料、特にイソソルビトールに基づく生物分解性ポリマー
US5277900A (en)	1994-01-11	Method for blood coagulation on hard tissues
JPH05503864A (ja)	1993-06-24	外科的縫合材料のための被覆材料としてのグリコール酸又は乳酸と多価アルコールとからなるポリマーの使用
Gresser et al.	1996	Bone cement, Part 1: Biopolymer for avulsive maxillofacial repair