CS221979B2 - Method of preparation the copolymere - Google Patents

Method of preparation the copolymere Download PDF

Info

Publication number: CS221979B2
Authority: CS; Czechoslovakia
Prior art keywords: acid; lactic acid; weight; glycolic; ion exchange
Prior art date: 1979-09-12

Application number

CS806134A

Other languages

Czech (cs)

English (en)

Inventor

Robert Nevin

Original Assignee

Lilly Co Eli

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.)

1979-09-12

Filing date

1980-09-10

Publication date

1983-04-29

1980-09-10 Application filed by Lilly Co Eli filed Critical Lilly Co Eli

1983-04-29 Publication of CS221979B2 publication Critical patent/CS221979B2/cs

Links

229920001577 copolymer Polymers 0.000 title claims abstract description 80
238000000034 method Methods 0.000 title claims description 28
238000002360 preparation method Methods 0.000 title claims description 10
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims abstract description 89
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims abstract description 71
239000004310 lactic acid Substances 0.000 claims abstract description 43
235000014655 lactic acid Nutrition 0.000 claims abstract description 43
229920003303 ion-exchange polymer Polymers 0.000 claims abstract description 16
239000003456 ion exchange resin Substances 0.000 claims abstract description 15
239000002253 acid Substances 0.000 claims abstract description 14
229920000642 polymer Polymers 0.000 claims description 25
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 22
239000003054 catalyst Substances 0.000 claims description 21
230000002378 acidificating effect Effects 0.000 claims description 18
239000011347 resin Substances 0.000 claims description 15
229920005989 resin Polymers 0.000 claims description 15
239000002685 polymerization catalyst Substances 0.000 claims description 14
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 11
238000006116 polymerization reaction Methods 0.000 claims description 8
235000013336 milk Nutrition 0.000 claims description 2
239000008267 milk Substances 0.000 claims description 2
210000004080 milk Anatomy 0.000 claims description 2
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims 4
125000003118 aryl group Chemical group 0.000 claims 1
239000000975 dye Substances 0.000 claims 1
125000000446 sulfanediyl group Chemical group *S* 0.000 claims 1
238000009833 condensation Methods 0.000 abstract description 5
230000005494 condensation Effects 0.000 abstract description 5
239000000203 mixture Substances 0.000 description 20
239000003814 drug Substances 0.000 description 15
241001465754 Metazoa Species 0.000 description 13
229920001467 poly(styrenesulfonates) Polymers 0.000 description 12
238000009472 formulation Methods 0.000 description 11
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
229940079593 drug Drugs 0.000 description 9
239000002904 solvent Substances 0.000 description 9
238000005342 ion exchange Methods 0.000 description 8
238000004090 dissolution Methods 0.000 description 6
238000011282 treatment Methods 0.000 description 6
239000004480 active ingredient Substances 0.000 description 5
239000000243 solution Substances 0.000 description 5
239000000126 substance Substances 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
230000015556 catabolic process Effects 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
238000013270 controlled release Methods 0.000 description 4
238000006731 degradation reaction Methods 0.000 description 4
235000014113 dietary fatty acids Nutrition 0.000 description 4
229930195729 fatty acid Natural products 0.000 description 4
239000000194 fatty acid Substances 0.000 description 4
238000004519 manufacturing process Methods 0.000 description 4
239000003960 organic solvent Substances 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
241000283690 Bos taurus Species 0.000 description 3
239000004793 Polystyrene Substances 0.000 description 3
239000013543 active substance Substances 0.000 description 3
150000004665 fatty acids Chemical class 0.000 description 3
238000001914 filtration Methods 0.000 description 3
238000005227 gel permeation chromatography Methods 0.000 description 3
229920002223 polystyrene Polymers 0.000 description 3
230000002035 prolonged effect Effects 0.000 description 3
210000004767 rumen Anatomy 0.000 description 3
231100000331 toxic Toxicity 0.000 description 3
230000002588 toxic effect Effects 0.000 description 3
238000005481 NMR spectroscopy Methods 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
239000004182 Tylosin Substances 0.000 description 2
229930194936 Tylosin Natural products 0.000 description 2
238000006065 biodegradation reaction Methods 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 2
244000309466 calf Species 0.000 description 2
239000007810 chemical reaction solvent Substances 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
238000009826 distribution Methods 0.000 description 2
238000005755 formation reaction Methods 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
235000013372 meat Nutrition 0.000 description 2
239000000178 monomer Substances 0.000 description 2
239000000047 product Substances 0.000 description 2
238000011321 prophylaxis Methods 0.000 description 2
238000000926 separation method Methods 0.000 description 2
239000007787 solid Substances 0.000 description 2
238000010561 standard procedure Methods 0.000 description 2
210000002784 stomach Anatomy 0.000 description 2
238000013268 sustained release Methods 0.000 description 2
239000012730 sustained-release form Substances 0.000 description 2
238000012360 testing method Methods 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
WBPYTXDJUQJLPQ-VMXQISHHSA-N tylosin Chemical compound O([C@@H]1[C@@H](C)O[C@H]([C@@H]([C@H]1N(C)C)O)O[C@@H]1[C@@H](C)[C@H](O)CC(=O)O[C@@H]([C@H](/C=C(\C)/C=C/C(=O)[C@H](C)C[C@@H]1CC=O)CO[C@H]1[C@@H]([C@H](OC)[C@H](O)[C@@H](C)O1)OC)CC)[C@H]1C[C@@](C)(O)[C@@H](O)[C@H](C)O1 WBPYTXDJUQJLPQ-VMXQISHHSA-N 0.000 description 2
235000019375 tylosin Nutrition 0.000 description 2
229960004059 tylosin Drugs 0.000 description 2
HQXKELRFXWJXNP-UHFFFAOYSA-N (1R)-N,N'-dicarbamimidoyl-O4-[3-formyl-O2-(O4-alpha-D-mannopyranosyl-2-methylamino-2-deoxy-alpha-L-glucopyranosyl)-5-deoxy-alpha-L-lyxofuranosyl]-streptamine Natural products OCC1OC(OC2C(C(C)OC2OC2C(C(O)C(N=C(N)N)C(O)C2O)N=C(N)N)(O)C=O)C(NC)C(O)C1OC1OC(CO)C(O)C(O)C1O HQXKELRFXWJXNP-UHFFFAOYSA-N 0.000 description 1
RKDVKSZUMVYZHH-UHFFFAOYSA-N 1,4-dioxane-2,5-dione Chemical compound O=C1COC(=O)CO1 RKDVKSZUMVYZHH-UHFFFAOYSA-N 0.000 description 1
OORRCVPWRPVJEK-UHFFFAOYSA-N 2-oxidanylethanoic acid Chemical compound OCC(O)=O.OCC(O)=O OORRCVPWRPVJEK-UHFFFAOYSA-N 0.000 description 1
JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
208000031295 Animal disease Diseases 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
VHKXXVVRRDYCIK-CWCPJSEDSA-N Narasin Chemical compound C[C@H]1C[C@H](C)[C@H]([C@@H](CC)C(O)=O)O[C@H]1[C@@H](C)[C@H](O)[C@H](C)C(=O)[C@H](CC)[C@@H]1[C@@H](C)C[C@@H](C)[C@@]2(C=C[C@@H](O)[C@@]3(O[C@@](C)(CC3)[C@@H]3O[C@@H](C)[C@@](O)(CC)CC3)O2)O1 VHKXXVVRRDYCIK-CWCPJSEDSA-N 0.000 description 1
VHKXXVVRRDYCIK-UHFFFAOYSA-N Narasin Natural products CC1CC(C)C(C(CC)C(O)=O)OC1C(C)C(O)C(C)C(=O)C(CC)C1C(C)CC(C)C2(C=CC(O)C3(OC(C)(CC3)C3OC(C)C(O)(CC)CC3)O2)O1 VHKXXVVRRDYCIK-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
241000207836 Olea <angiosperm> Species 0.000 description 1
240000007594 Oryza sativa Species 0.000 description 1
235000007164 Oryza sativa Nutrition 0.000 description 1
206010035664 Pneumonia Diseases 0.000 description 1
241000282849 Ruminantia Species 0.000 description 1
229910000831 Steel Inorganic materials 0.000 description 1
241000282887 Suidae Species 0.000 description 1
239000004098 Tetracycline Substances 0.000 description 1
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
239000000654 additive Substances 0.000 description 1
230000000996 additive effect Effects 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
239000003098 androgen Substances 0.000 description 1
229940030486 androgens Drugs 0.000 description 1
239000003674 animal food additive Substances 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
229960001948 caffeine Drugs 0.000 description 1
VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
235000013339 cereals Nutrition 0.000 description 1
238000013329 compounding Methods 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
239000003405 delayed action preparation Substances 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
230000004069 differentiation Effects 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
239000003623 enhancer Substances 0.000 description 1
229940011871 estrogen Drugs 0.000 description 1
239000000262 estrogen Substances 0.000 description 1
239000003925 fat Substances 0.000 description 1
235000019197 fats Nutrition 0.000 description 1
-1 fatty acid ester Chemical class 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
235000013305 food Nutrition 0.000 description 1
239000011521 glass Substances 0.000 description 1
125000003827 glycol group Chemical group 0.000 description 1
239000007952 growth promoter Substances 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
239000003688 hormone derivative Substances 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
208000015181 infectious disease Diseases 0.000 description 1
230000000968 intestinal effect Effects 0.000 description 1
RUTXIHLAWFEWGM-UHFFFAOYSA-H iron(3+) sulfate Chemical compound [Fe+3].[Fe+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O RUTXIHLAWFEWGM-UHFFFAOYSA-H 0.000 description 1
229910000360 iron(III) sulfate Inorganic materials 0.000 description 1
238000002955 isolation Methods 0.000 description 1
JJTUDXZGHPGLLC-UHFFFAOYSA-N lactide Chemical compound CC1OC(=O)C(C)OC1=O JJTUDXZGHPGLLC-UHFFFAOYSA-N 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000011159 matrix material Substances 0.000 description 1
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
229910001507 metal halide Inorganic materials 0.000 description 1
150000005309 metal halides Chemical class 0.000 description 1
229910044991 metal oxide Inorganic materials 0.000 description 1
150000004706 metal oxides Chemical class 0.000 description 1
125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
229960001851 narasin Drugs 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
235000015097 nutrients Nutrition 0.000 description 1
239000003921 oil Substances 0.000 description 1
235000019198 oils Nutrition 0.000 description 1
239000002245 particle Substances 0.000 description 1
230000003285 pharmacodynamic effect Effects 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
231100000614 poison Toxicity 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
239000002861 polymer material Substances 0.000 description 1
238000012805 post-processing Methods 0.000 description 1
238000012545 processing Methods 0.000 description 1
229940002612 prodrug Drugs 0.000 description 1
239000000651 prodrug Substances 0.000 description 1
239000000583 progesterone congener Substances 0.000 description 1
229940095055 progestogen systemic hormonal contraceptives Drugs 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
238000002798 spectrophotometry method Methods 0.000 description 1
239000010959 steel Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 1
235000019364 tetracycline Nutrition 0.000 description 1
150000003522 tetracyclines Chemical class 0.000 description 1
229940040944 tetracyclines Drugs 0.000 description 1
125000005323 thioketone group Chemical group 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
239000003440 toxic substance Substances 0.000 description 1
239000001993 wax Substances 0.000 description 1
239000008096 xylene Substances 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
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- 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
- 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

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Inorganic Chemistry (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Polyesters Or Polycarbonates (AREA)
Medicinal Preparation (AREA)
Biological Depolymerization Polymers (AREA)

CS806134A 1979-09-12 1980-09-10 Method of preparation the copolymere CS221979B2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US06/075,296 US4273920A (en)	1979-09-12	1979-09-12	Polymerization process and product

Publications (1)

Publication Number	Publication Date
CS221979B2 true CS221979B2 (en)	1983-04-29

Family

ID=22124778

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS806134A CS221979B2 (en)	1979-09-12	1980-09-10	Method of preparation the copolymere

Country Status (31)

Country	Link
US (1)	US4273920A (fr)
EP (1)	EP0026599B1 (fr)
JP (2)	JPS5645920A (fr)
AR (1)	AR221173A1 (fr)
AT (1)	AT380689B (fr)
AU (1)	AU539130B2 (fr)
BE (1)	BE885182A (fr)
BG (1)	BG41132A3 (fr)
CA (1)	CA1185048A (fr)
CH (1)	CH648048A5 (fr)
CS (1)	CS221979B2 (fr)
DD (1)	DD153125A5 (fr)
DE (1)	DE3068116D1 (fr)
DK (1)	DK155093C (fr)
EG (1)	EG14381A (fr)
ES (1)	ES8106542A1 (fr)
FI (1)	FI66412C (fr)
FR (1)	FR2464973A1 (fr)
GB (1)	GB2058808B (fr)
GR (1)	GR69961B (fr)
GT (1)	GT198065361A (fr)
HU (1)	HU191807B (fr)
IE (1)	IE50236B1 (fr)
IL (1)	IL61024A (fr)
IT (1)	IT1141040B (fr)
NZ (1)	NZ194902A (fr)
PH (1)	PH15272A (fr)
PL (1)	PL129779B1 (fr)
PT (1)	PT71794B (fr)
RO (1)	RO80864A (fr)
ZA (1)	ZA805629B (fr)

Families Citing this family (89)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4333919A (en) *	1979-09-12	1982-06-08	Eli Lilly And Company	Growth promotant controlled release formulations and method of treatment
IE52535B1 (en) *	1981-02-16	1987-12-09	Ici Plc	Continuous release pharmaceutical compositions
US4716964A (en) *	1981-08-10	1988-01-05	Exxon Production Research Company	Use of degradable ball sealers to seal casing perforations in well treatment fluid diversion
US4523591A (en) *	1982-10-22	1985-06-18	Kaplan Donald S	Polymers for injection molding of absorbable surgical devices
FR2537980B1 (fr) *	1982-12-17	1986-12-19	Sandoz Sa	Derives d'acides hydroxycarboxyliques oligomeres, leur preparation et leur utilisation
US4470416A (en) *	1983-06-17	1984-09-11	Ethicon, Inc.	Copolymers of lactide and/or glycolide with 1,5-dioxepan-2-one
CH656884A5 (de) *	1983-08-26	1986-07-31	Sandoz Ag	Polyolester, deren herstellung und verwendung.
US4594407A (en) *	1983-09-20	1986-06-10	Allied Corporation	Prosthetic devices derived from krebs-cycle dicarboxylic acids and diols
JPS60100516A (ja) *	1983-11-04	1985-06-04	Takeda Chem Ind Ltd	徐放型マイクロカプセルの製造法
ATE142236T1 (de) *	1984-03-06	1996-09-15	United States Surgical Corp	Ein verfahren zur herstellung von zwei-phasen- zusammensetzungen für absorbierbare chirurgische ausrüstungen
US4649042A (en) *	1984-05-31	1987-03-10	Eli Lilly And Company	Rumen delivery device
JPH0678425B2 (ja) *	1984-07-06	1994-10-05	和光純薬工業株式会社	重合体の新規製造法
CA1256638A (fr) *	1984-07-06	1989-06-27	Motoaki Tanaka	Polymere, et sa production
DE3428640A1 (de) *	1984-08-03	1986-02-06	Akzo Gmbh, 5600 Wuppertal	Mikroporoese, pulverfoermige polylactide
US4595713A (en) *	1985-01-22	1986-06-17	Hexcel Corporation	Medical putty for tissue augmentation
DE3678308D1 (de) *	1985-02-07	1991-05-02	Takeda Chemical Industries Ltd	Verfahren zur herstellung von mikrokapseln.
JP2551756B2 (ja) *	1985-05-07	1996-11-06	武田薬品工業株式会社	ポリオキシカルボン酸エステルおよびその製造法
US5618547A (en) *	1985-05-20	1997-04-08	British Technology Group Limited	Control of ectoparasites
JPH0610252B2 (ja) *	1985-08-21	1994-02-09	和光純薬工業株式会社	重合体の製造法
US5061281A (en) *	1985-12-17	1991-10-29	Allied-Signal Inc.	Bioresorbable polymers and implantation devices thereof
GB8609537D0 (en) *	1986-04-18	1986-05-21	Ici Plc	Polyesters
US4744365A (en) *	1986-07-17	1988-05-17	United States Surgical Corporation	Two-phase compositions for absorbable surgical devices
DE3641692A1 (de) *	1986-12-06	1988-06-09	Boehringer Ingelheim Kg	Katalysatorfreie resorbierbare homopolymere und copolymere
SE8701479L (sv) *	1987-04-09	1988-10-10	Carbomatrix Ab	Metod foer inneslutning av biologiskt verksamma preparat samt anvaendning daerav
US4804691A (en) *	1987-08-28	1989-02-14	Richards Medical Company	Method for making a biodegradable adhesive for soft living tissue
OA09249A (fr) *	1988-12-19	1992-06-30	Lilly Co Eli	Composés de macrolides.
JP2986509B2 (ja) *	1989-05-26	1999-12-06	三井化学株式会社	変性ポリエステル樹脂組成物、その製造方法、およびその用途
DE4005415C2 (de) *	1990-02-21	1996-04-11	Boehringer Ingelheim Kg	Verfahren zum Herstellen von Polyestern auf der Basis von Hydroxycarbonsäuren
US5302694A (en) *	1990-02-21	1994-04-12	Boehringer Ingelheim Gmbh	Process for preparing polyesters based on hydroxycarboxylic acids
DE69129770T2 (de) *	1990-04-13	1998-11-19	Takeda Chemical Industries Ltd	Biologisch abbaubare hochmolekulare Polymere, ihre Herstellung und ihre Verwendung
MY108621A (en) *	1990-08-01	1996-10-31	Novartis Ag	Polylactide preparation and purification
US6353030B1 (en) *	1990-08-01	2002-03-05	Novartis Ag	Relating to organic compounds
US5108422A (en) *	1990-10-22	1992-04-28	United States Surgical Corporation	Skin fastener
US5593423A (en) *	1990-10-22	1997-01-14	United States Surgical Corporation	Skin fastener
US5320624A (en) *	1991-02-12	1994-06-14	United States Surgical Corporation	Blends of glycolide and/or lactide polymers and caprolactone and/or trimethylene carbonate polymers and absorbable surgical devices made therefrom
US6228954B1 (en)	1991-02-12	2001-05-08	United States Surgical Corporation	Blends of glycolide and/or lactide polymers and caprolactone and/or trimethylene carbonate polymers and absorabable surgical devices made therefrom
IT1249045B (it) *	1991-02-21	1995-02-11	Himont Inc	Processo per la sintesi allo stato solido di polimeri dell'acido lattico e prodotti cosi ottenuti
US5232648A (en) *	1991-07-19	1993-08-03	United States Surgical Corporation	Bioabsorbable melt spun fiber based on glycolide-containing copolymer
US5206341A (en) *	1991-11-21	1993-04-27	Southern Research Institute	Polymers from hydroxy acids and polycarboxylic acids
ES2139646T3 (es) *	1991-12-19	2000-02-16	Mitsui Chemicals Inc	Acido polihidroxido carboxilico y su procedimiento de obtencion.
US5258488A (en) *	1992-01-24	1993-11-02	Cargill, Incorporated	Continuous process for manufacture of lactide polymers with controlled optical purity
US6326458B1 (en)	1992-01-24	2001-12-04	Cargill, Inc.	Continuous process for the manufacture of lactide and lactide polymers
US6005067A (en) *	1992-01-24	1999-12-21	Cargill Incorporated	Continuous process for manufacture of lactide polymers with controlled optical purity
US5247059A (en) *	1992-01-24	1993-09-21	Cargill, Incorporated	Continuous process for the manufacture of a purified lactide from esters of lactic acid
US5247058A (en) *	1992-01-24	1993-09-21	Cargill, Incorporated	Continuous process for manufacture of lactide polymers with controlled optical purity
US5142023A (en) *	1992-01-24	1992-08-25	Cargill, Incorporated	Continuous process for manufacture of lactide polymers with controlled optical purity
US5338822A (en) *	1992-10-02	1994-08-16	Cargill, Incorporated	Melt-stable lactide polymer composition and process for manufacture thereof
DE69330046T2 (de) *	1992-10-02	2001-11-15	Cargill, Inc.	Schmelzstabiles lactidpolymergewebe und verfahren zu seiner herstellung
NZ256978A (en) *	1992-10-02	1996-05-28	Cargill Inc	Paper product coated with a poly(lactide) composition comprising no more than 5 wt % lactide monomer, the poly(lactide) having a number average mw of 10,000 to 200,000
US6005068A (en)	1992-10-02	1999-12-21	Cargill Incorporated	Melt-stable amorphous lactide polymer film and process for manufacture thereof
US5591606A (en) *	1992-11-06	1997-01-07	Dowelanco	Process for the production of A83543 compounds with Saccharopolyspora spinosa
TW333456B (en) *	1992-12-07	1998-06-11	Takeda Pharm Ind Co Ltd	A pharmaceutical composition of sustained-release preparation the invention relates to a pharmaceutical composition of sustained-release preparation which comprises a physiologically active peptide.
US5444143A (en) *	1992-12-25	1995-08-22	Mitsui Toatsu Chemicals, Inc.	Preparation process of polyhydroxycarboxylic acid
WO1994020518A1 (fr) *	1993-03-12	1994-09-15	Dowelanco	Nouveaux composes a83543 et procede de production desdits composes
KR970002523B1 (en) *	1993-04-24	1997-03-05	Korea Inst Sci & Tech	Biodegradable polylactic acid having improved properties and method for manufacturing the same
US5522841A (en) *	1993-05-27	1996-06-04	United States Surgical Corporation	Absorbable block copolymers and surgical articles fabricated therefrom
US5403347A (en) *	1993-05-27	1995-04-04	United States Surgical Corporation	Absorbable block copolymers and surgical articles fabricated therefrom
WO1995010577A1 (fr)	1993-10-15	1995-04-20	H.B. Fuller Licensing & Financing Inc.	Adhesifs thermofusibles biodegradables/recyclables en compost constitues de polyester d'acide lactique
US5431679A (en) *	1994-03-10	1995-07-11	United States Surgical Corporation	Absorbable block copolymers and surgical articles fabricated therefrom
US5543202A (en) *	1994-03-14	1996-08-06	Kimberly-Clark Corporation	Process for producing a crimp-bonded fibrous cellulosic laminate
CN1058736C (zh) *	1994-05-27	2000-11-22	北京市星辰现代控制工程研究所	生物降解组合物及其制备方法和应用
US5578662A (en)	1994-07-22	1996-11-26	United States Surgical Corporation	Bioabsorbable branched polymers containing units derived from dioxanone and medical/surgical devices manufactured therefrom
US6339130B1 (en) *	1994-07-22	2002-01-15	United States Surgical Corporation	Bioabsorbable branched polymers containing units derived from dioxanone and medical/surgical devices manufactured therefrom
US6206908B1 (en)	1994-09-16	2001-03-27	United States Surgical Corporation	Absorbable polymer and surgical articles fabricated therefrom
CA2158420C (fr)	1994-09-16	2007-05-01	Mark S. Roby	Polymeres absorbables et articles chirurgicaux fabriques a partir de ceux-ci
US5618313A (en) *	1994-10-11	1997-04-08	United States Surgical Corporation	Absorbable polymer and surgical articles fabricated therefrom
US5770683A (en)	1994-11-02	1998-06-23	Mitsui Toatsu Chemicals, Inc.	Preparation process of polyhydroxycarboxylic acid
US5997568A (en) *	1996-01-19	1999-12-07	United States Surgical Corporation	Absorbable polymer blends and surgical articles fabricated therefrom
US6001981A (en) *	1996-06-13	1999-12-14	Dow Agrosciences Llc	Synthetic modification of Spinosyn compounds
US5756651A (en) *	1996-07-17	1998-05-26	Chronopol, Inc.	Impact modified polylactide
US6191236B1 (en)	1996-10-11	2001-02-20	United States Surgical Corporation	Bioabsorbable suture and method of its manufacture
US6007565A (en) *	1997-09-05	1999-12-28	United States Surgical	Absorbable block copolymers and surgical articles fabricated therefrom
US6277927B1 (en)	1997-11-26	2001-08-21	United States Surgical Corporation	Absorbable block copolymers and surgical articles fabricated therefrom
JPH11203837A (ja)	1998-01-16	1999-07-30	Sony Corp	編集システムおよび編集方法
AR023940A1 (es)	2000-05-03	2002-09-04	Eriochem Sa	Procedimiento para la produccion de microcapsulas de liberacion prolongada de peptidos solubles en agua
CN1269870C (zh) *	2000-08-07	2006-08-16	和光纯药工业株式会社	乳酸聚合物及其制备方法
AU2001290515B2 (en)	2000-08-16	2007-02-01	Covidien Lp	High consistency absorbable polymeric resin
TWI332407B (en) *	2001-06-29	2010-11-01	Takeda Chemical Industries Ltd	Controlled release composition and method of producting the same
JP4612239B2 (ja) *	2001-07-18	2011-01-12	三井化学株式会社	生体吸収性ポリヒドロキシカルボン酸の製造方法
US7163545B2 (en) *	2002-07-29	2007-01-16	Mayo Foundation For Medical Education And Research	Spinal cord surgical implant
KR100684682B1 (ko) *	2002-09-24	2007-02-22	아사히 가세이 케미칼즈 가부시키가이샤	글리콜산 공중합체 및 그의 제조 방법
EP1440992A1 (fr) *	2003-01-21	2004-07-28	Société de Conseils de Recherches et d'Applications Scientifiques ( S.C.R.A.S.)	Système catalytique de (co)polymérisation du lactide et du glycolide
FR2867698B1 (fr) *	2004-03-16	2007-11-16	Beaufour Ipsen S C R A S	Systeme catalttique de (co) oligomerisation du lactide et du glycolide
WO2005105908A1 (fr) *	2004-04-28	2005-11-10	Keio University	Procédé de dépolymérisation de polymère ayant un lien d'ester dans la chaine principale et procédé pour produire le polymere ayant le lien d'ester dans la chaine princpale depuis le produit de dépolymérisation
MX2009006653A (es)	2006-12-18	2009-07-02	Takeda Pharmaceutical	Composicion de liberacion prolongada y metodo para producirla.
CN101284883B (zh) *	2008-05-14	2011-02-16	西北大学	聚乳酸-壳聚糖接枝共聚物的制备方法
RU2404198C2 (ru) *	2008-11-12	2010-11-20	Федеральное государственное унитарное предприятие "Ордена Трудового Красного Знамени Научно-исследовательский физико-химический институт имени Л.Я. Карпова"	Способ получения сополимеров стирола с молочной кислотой
CN103300120B (zh) *	2013-06-25	2015-04-22	南京工业大学	一种绿色家禽家畜脱毛剂及其制备方法
IL272809B2 (en)	2017-08-31	2025-05-01	Evonik Corp	Improved resorbable polymer purification process

Family Cites Families (18)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2362511A (en) *	1939-11-21	1944-11-14	Du Pont	Modified glycolide resins
US2703316A (en) *	1951-06-05	1955-03-01	Du Pont	Polymers of high melting lactide
US2758987A (en) *	1952-06-05	1956-08-14	Du Pont	Optically active homopolymers containing but one antipodal species of an alpha-monohydroxy monocarboxylic acid
US3268487A (en) *	1963-12-23	1966-08-23	Shell Oil Co	Process for polymerization of lactides
US3535419A (en) *	1965-12-15	1970-10-20	Syntex Corp	Veterinary compositions and methods
US3442871A (en) *	1966-05-04	1969-05-06	American Cyanamid Co	Process for polymerizing a glycolide
US3458622A (en) *	1967-04-07	1969-07-29	Squibb & Sons Inc	Controlled release tablet
US3887699A (en) *	1969-03-24	1975-06-03	Seymour Yolles	Biodegradable polymeric article for dispensing drugs
US3773919A (en) *	1969-10-23	1973-11-20	Du Pont	Polylactide-drug mixtures
BE758156R (fr) *	1970-05-13	1971-04-28	Ethicon Inc	Element de suture absorbable et sa
US3736646A (en) *	1971-10-18	1973-06-05	American Cyanamid Co	Method of attaching surgical needles to multifilament polyglycolic acid absorbable sutures
US3839297A (en) *	1971-11-22	1974-10-01	Ethicon Inc	Use of stannous octoate catalyst in the manufacture of l(-)lactide-glycolide copolymer sutures
US3982543A (en) *	1973-04-24	1976-09-28	American Cyanamid Company	Reducing capillarity of polyglycolic acid sutures
US3991766A (en) *	1973-05-31	1976-11-16	American Cyanamid Company	Controlled release of medicaments using polymers from glycolic acid
US4144317A (en) *	1975-05-30	1979-03-13	Alza Corporation	Device consisting of copolymer having acetoxy groups for delivering drugs
US4011312A (en) *	1975-06-25	1977-03-08	American Home Products Corporation	Prolonged release drug form for the treatment of bovine mastitis
US4010196A (en) *	1975-06-25	1977-03-01	American Home Products Corporation	Linear polyester salts
ZA782039B (en) *	1977-05-23	1979-09-26	American Cyanamid Co	Surgical articles

1979
- 1979-09-12 US US06/075,296 patent/US4273920A/en not_active Expired - Lifetime
1980
- 1980-09-09 NZ NZ194902A patent/NZ194902A/xx unknown
- 1980-09-09 AR AR282459A patent/AR221173A1/es active
- 1980-09-09 GR GR62846A patent/GR69961B/el unknown
- 1980-09-09 RO RO80102132A patent/RO80864A/fr unknown
- 1980-09-09 AU AU62166/80A patent/AU539130B2/en not_active Expired
- 1980-09-09 PH PH24558A patent/PH15272A/en unknown
- 1980-09-09 PL PL1980226653A patent/PL129779B1/pl unknown
- 1980-09-10 FR FR8019582A patent/FR2464973A1/fr active Granted
- 1980-09-10 GT GT198065361A patent/GT198065361A/es unknown
- 1980-09-10 IL IL61024A patent/IL61024A/xx not_active IP Right Cessation
- 1980-09-10 CA CA000360018A patent/CA1185048A/fr not_active Expired
- 1980-09-10 AT AT0455380A patent/AT380689B/de not_active IP Right Cessation
- 1980-09-10 CH CH6807/80A patent/CH648048A5/fr not_active IP Right Cessation
- 1980-09-10 EG EG559/80A patent/EG14381A/xx active
- 1980-09-10 FI FI802840A patent/FI66412C/fi not_active IP Right Cessation
- 1980-09-10 CS CS806134A patent/CS221979B2/cs unknown
- 1980-09-11 DK DK387380A patent/DK155093C/da not_active IP Right Cessation
- 1980-09-11 DE DE8080303198T patent/DE3068116D1/de not_active Expired
- 1980-09-11 JP JP12664280A patent/JPS5645920A/ja active Granted
- 1980-09-11 GB GB8029392A patent/GB2058808B/en not_active Expired
- 1980-09-11 BE BE1/9957A patent/BE885182A/fr not_active IP Right Cessation
- 1980-09-11 ES ES494974A patent/ES8106542A1/es not_active Expired
- 1980-09-11 HU HU802235A patent/HU191807B/hu not_active IP Right Cessation
- 1980-09-11 PT PT71794A patent/PT71794B/pt not_active IP Right Cessation
- 1980-09-11 BG BG049032A patent/BG41132A3/xx unknown
- 1980-09-11 IT IT24607/80A patent/IT1141040B/it active
- 1980-09-11 IE IE1902/80A patent/IE50236B1/en not_active IP Right Cessation
- 1980-09-11 EP EP80303198A patent/EP0026599B1/fr not_active Expired
- 1980-09-11 ZA ZA00805629A patent/ZA805629B/xx unknown
- 1980-09-12 DD DD80223870A patent/DD153125A5/de not_active IP Right Cessation
1988
- 1988-04-26 JP JP63107377A patent/JPH0198617A/ja active Granted

Also Published As

Publication number	Publication date
AR221173A1 (es)	1980-12-30
GT198065361A (es)	1982-03-04
FI802840A7 (fi)	1981-03-13
PT71794A (en)	1980-10-01
AU6216680A (en)	1981-03-19
NZ194902A (en)	1983-05-31
DK155093C (da)	1989-06-19
HU191807B (en)	1987-04-28
IE801902L (en)	1981-03-12
IE50236B1 (en)	1986-03-05
ES494974A0 (es)	1981-08-16
EP0026599A1 (fr)	1981-04-08
ES8106542A1 (es)	1981-08-16
RO80864A (fr)	1983-02-01
JPH0198617A (ja)	1989-04-17
DK155093B (da)	1989-02-06
FR2464973A1 (fr)	1981-03-20
DE3068116D1 (en)	1984-07-12
IL61024A0 (en)	1980-11-30
IT8024607A0 (it)	1980-09-11
JPS5645920A (en)	1981-04-25
GB2058808B (en)	1983-11-16
JPH0445525B2 (fr)	1992-07-27
AU539130B2 (en)	1984-09-13
PL129779B1 (en)	1984-06-30
FR2464973B1 (fr)	1983-06-10
IT1141040B (it)	1986-10-01
CH648048A5 (fr)	1985-02-28
EP0026599B1 (fr)	1984-06-06
EG14381A (en)	1983-12-31
GB2058808A (en)	1981-04-15
DK387380A (da)	1981-03-13
DD153125A5 (de)	1981-12-23
FI66412B (fi)	1984-06-29
BE885182A (fr)	1981-03-11
AT380689B (de)	1986-06-25
FI66412C (fi)	1984-10-10
GR69961B (fr)	1982-07-22
ZA805629B (en)	1982-04-28
PL226653A1 (fr)	1981-10-16
JPH0121166B2 (fr)	1989-04-20
IL61024A (en)	1983-02-23
US4273920A (en)	1981-06-16
PT71794B (en)	1981-07-07
ATA455380A (de)	1985-11-15
BG41132A3 (bg)	1987-04-15
CA1185048A (fr)	1985-04-02
PH15272A (en)	1982-11-02

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CS221979B2 (en)	1983-04-29	Method of preparation the copolymere
EP0025698B1 (fr)	1984-06-13	Formulations à libération contrôlée
FI97688C (fi)	1997-02-10	Menetelmä mikrohiukkasten muodossa olevan farmaseuttisen koostumuksen valmistamiseksi
US4331652A (en)	1982-05-25	Controlled release parasitic formulations and method
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EP0025699B1 (fr)	1983-10-12	Dispositif pour administrer des médicaments à des ruminants
JPH01500034A (ja)	1989-01-12	ワクチンおよび植込剤
CA1162781A (fr)	1984-02-28	Compositions a debit reglable, activant la croissance, et methode de traitement
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BE1001687A5 (fr)	1990-02-06	Composition a base de polyesters pour la liberation controlee de substances medicamenteuses.
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