DE10055742B4 - Neue Polyester, Verfahren zu ihrer Herstellung und aus den Polyestern hergestellte Depot-Arzneiformen - Google Patents
Neue Polyester, Verfahren zu ihrer Herstellung und aus den Polyestern hergestellte Depot-Arzneiformen Download PDFInfo
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- DE10055742B4 DE10055742B4 DE10055742A DE10055742A DE10055742B4 DE 10055742 B4 DE10055742 B4 DE 10055742B4 DE 10055742 A DE10055742 A DE 10055742A DE 10055742 A DE10055742 A DE 10055742A DE 10055742 B4 DE10055742 B4 DE 10055742B4
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- Prior art keywords
- polyester
- extruder
- electrolyte
- polyesters
- resorbable
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- 108010021336 lanreotide Proteins 0.000 description 1
- 229960002437 lanreotide Drugs 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 229940039781 leptin Drugs 0.000 description 1
- NRYBAZVQPHGZNS-ZSOCWYAHSA-N leptin Chemical compound O=C([C@H](CO)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)CNC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](N)CC(C)C)CCSC)N1CCC[C@H]1C(=O)NCC(=O)N[C@@H](CS)C(O)=O NRYBAZVQPHGZNS-ZSOCWYAHSA-N 0.000 description 1
- 210000000265 leukocyte Anatomy 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 210000001616 monocyte Anatomy 0.000 description 1
- 230000000921 morphogenic effect Effects 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 239000002077 nanosphere Substances 0.000 description 1
- 230000001452 natriuretic effect Effects 0.000 description 1
- 239000004309 nisin Substances 0.000 description 1
- 235000010297 nisin Nutrition 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- XNOPRXBHLZRZKH-DSZYJQQASA-N oxytocin Chemical compound C([C@H]1C(=O)N[C@H](C(N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CSSC[C@H](N)C(=O)N1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC(C)C)C(=O)NCC(N)=O)=O)[C@@H](C)CC)C1=CC=C(O)C=C1 XNOPRXBHLZRZKH-DSZYJQQASA-N 0.000 description 1
- 229960001723 oxytocin Drugs 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000002831 pharmacologic agent Substances 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229920001606 poly(lactic acid-co-glycolic acid) Polymers 0.000 description 1
- 229920001481 poly(stearyl methacrylate) Polymers 0.000 description 1
- 229920002959 polymer blend Polymers 0.000 description 1
- 238000012667 polymer degradation Methods 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 239000003910 polypeptide antibiotic agent Substances 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 238000009117 preventive therapy Methods 0.000 description 1
- 229940097325 prolactin Drugs 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
- 229960000380 propiolactone Drugs 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- 108010061338 ranpirnase Proteins 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 239000012088 reference solution Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- NHXLMOGPVYXJNR-ATOGVRKGSA-N somatostatin Chemical compound C([C@H]1C(=O)N[C@H](C(N[C@@H](CO)C(=O)N[C@@H](CSSC[C@@H](C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CC=2C3=CC=CC=C3NC=2)C(=O)N[C@@H](CCCCN)C(=O)N[C@H](C(=O)N1)[C@@H](C)O)NC(=O)CNC(=O)[C@H](C)N)C(O)=O)=O)[C@H](O)C)C1=CC=CC=C1 NHXLMOGPVYXJNR-ATOGVRKGSA-N 0.000 description 1
- 229960000553 somatostatin Drugs 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical group C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- 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 description 1
- 239000006208 topical dosage form Substances 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- VBEQCZHXXJYVRD-GACYYNSASA-N uroanthelone Chemical compound C([C@@H](C(=O)N[C@H](C(=O)N[C@@H](CS)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CS)C(=O)N[C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)NCC(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CS)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O)C(C)C)[C@@H](C)O)NC(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H](CCSC)NC(=O)[C@H](CS)NC(=O)[C@@H](NC(=O)CNC(=O)CNC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CS)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)CNC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CS)NC(=O)CNC(=O)[C@H]1N(CCC1)C(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@@H](N)CC(N)=O)C(C)C)[C@@H](C)CC)C1=CC=C(O)C=C1 VBEQCZHXXJYVRD-GACYYNSASA-N 0.000 description 1
- 229960005486 vaccine Drugs 0.000 description 1
- 229960003726 vasopressin Drugs 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 150000004823 xylans Chemical class 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 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
- C08G63/02—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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
- A61K9/1605—Excipients; Inactive ingredients
- A61K9/1629—Organic macromolecular compounds
- A61K9/1641—Organic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyethylene glycol, poloxamers
- A61K9/1647—Polyesters, e.g. poly(lactide-co-glycolide)
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Polymers & Plastics (AREA)
- Diabetes (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Endocrinology (AREA)
- Emergency Medicine (AREA)
- Polyesters Or Polycarbonates (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10055742A DE10055742B4 (de) | 2000-11-10 | 2000-11-10 | Neue Polyester, Verfahren zu ihrer Herstellung und aus den Polyestern hergestellte Depot-Arzneiformen |
| AT01990396T ATE271083T1 (de) | 2000-11-10 | 2001-11-08 | Neue polyester, verfahren zu ihrer herstellung und aus den polyestern hergestellte depot- arzneiformen |
| AU2002229539A AU2002229539A1 (en) | 2000-11-10 | 2001-11-08 | Novel polyesters, method for producing the same and depot medicaments produced from these polyesters |
| EP01990396A EP1345979B1 (de) | 2000-11-10 | 2001-11-08 | Neue polyester, verfahren zu ihrer herstellung und aus den polyestern hergestellte depot-arzneiformen |
| DE50102886T DE50102886D1 (de) | 2000-11-10 | 2001-11-08 | Neue polyester, verfahren zu ihrer herstellung und aus den polyestern hergestellte depot-arzneiformen |
| ES01990396T ES2225636T3 (es) | 2000-11-10 | 2001-11-08 | Nuevos poliesteres, procedimiento para su preparacion y formas medicamentosas de deposito preparadas a partir de estos poliesteres. |
| JP2002541975A JP2004514002A (ja) | 2000-11-10 | 2001-11-08 | 新規ポリエステル、その製法および前記ポリエステルから製造されるデポー剤 |
| PCT/EP2001/012888 WO2002038646A2 (de) | 2000-11-10 | 2001-11-08 | Neue polyester, verfahren zu ihrer herstellung und aus den polyestern hergestellte depot-arzneiformen |
| US10/416,472 US7087247B2 (en) | 2000-11-10 | 2001-11-08 | Polyesters, method for producing same, and depot medicaments produced from these polyesters |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10055742A DE10055742B4 (de) | 2000-11-10 | 2000-11-10 | Neue Polyester, Verfahren zu ihrer Herstellung und aus den Polyestern hergestellte Depot-Arzneiformen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE10055742A1 DE10055742A1 (de) | 2002-05-29 |
| DE10055742B4 true DE10055742B4 (de) | 2006-05-11 |
Family
ID=7662818
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE10055742A Expired - Fee Related DE10055742B4 (de) | 2000-11-10 | 2000-11-10 | Neue Polyester, Verfahren zu ihrer Herstellung und aus den Polyestern hergestellte Depot-Arzneiformen |
| DE50102886T Expired - Lifetime DE50102886D1 (de) | 2000-11-10 | 2001-11-08 | Neue polyester, verfahren zu ihrer herstellung und aus den polyestern hergestellte depot-arzneiformen |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE50102886T Expired - Lifetime DE50102886D1 (de) | 2000-11-10 | 2001-11-08 | Neue polyester, verfahren zu ihrer herstellung und aus den polyestern hergestellte depot-arzneiformen |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US7087247B2 (cg-RX-API-DMAC7.html) |
| EP (1) | EP1345979B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JP2004514002A (cg-RX-API-DMAC7.html) |
| AT (1) | ATE271083T1 (cg-RX-API-DMAC7.html) |
| AU (1) | AU2002229539A1 (cg-RX-API-DMAC7.html) |
| DE (2) | DE10055742B4 (cg-RX-API-DMAC7.html) |
| ES (1) | ES2225636T3 (cg-RX-API-DMAC7.html) |
| WO (1) | WO2002038646A2 (cg-RX-API-DMAC7.html) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100354270B1 (ko) | 1993-11-19 | 2003-02-11 | 알커메스 컨트롤드 테라포이틱스 인코퍼레이티드 Ii | 마이크로캡슐화된3-피페리디닐-치환된1,2-벤즈이속사졸및1,2-벤즈이소티아졸 |
| KR100794081B1 (ko) * | 2000-04-12 | 2008-01-10 | 산꼬 가가꾸 고교 가부시끼가이샤 | 제전성 조성물 |
| DE10041478A1 (de) | 2000-08-24 | 2002-03-14 | Sanol Arznei Schwarz Gmbh | Neue pharmazeutische Zusammensetzung |
| DE10041479A1 (de) * | 2000-08-24 | 2002-03-14 | Sanol Arznei Schwarz Gmbh | Neue pharmazeutische Zusammensetzung zur Verabreichung von N-0923 |
| DE10055857A1 (de) * | 2000-11-10 | 2002-08-22 | Creative Peptides Sweden Ab Dj | Neue pharmazeutische Depotformulierung |
| DE10334188B4 (de) | 2003-07-26 | 2007-07-05 | Schwarz Pharma Ag | Verwendung von Rotigotin zur Behandlung von Depressionen |
| DE10361258A1 (de) | 2003-12-24 | 2005-07-28 | Schwarz Pharma Ag | Verwendung von substituierten 2-Aminotetralinen zur vorbeugenden Behandlung von Morbus Parkinson |
| DE102004014841B4 (de) | 2004-03-24 | 2006-07-06 | Schwarz Pharma Ag | Verwendung von Rotigotin zur Behandlung und Prävention des Parkinson-Plus-Syndroms |
| PL1797871T3 (pl) | 2004-09-21 | 2015-07-31 | Shandong luye pharmaceutical co ltd | Długo działający preparat o przedłużonym uwalnianiu zawierający agonistę receptora dopaminowego i sposób jego wytwarzania |
| EP2041346B1 (en) | 2006-07-14 | 2011-12-21 | Kimberly-Clark Worldwide, Inc. | Biodegradable polyactic acid for use in nonwoven webs |
| US8710172B2 (en) | 2006-07-14 | 2014-04-29 | Kimberly-Clark Worldwide, Inc. | Biodegradable aliphatic-aromatic copolyester for use in nonwoven webs |
| EP2044251B1 (en) | 2006-07-14 | 2019-10-02 | NatureWorks LLC | Biodegradable aliphatic polyester for use in nonwoven webs |
| JP2009544630A (ja) * | 2006-07-26 | 2009-12-17 | デイアメデイカ・インコーポレイテツド | 代謝障害の診断及び治療方法 |
| US8518311B2 (en) | 2007-08-22 | 2013-08-27 | Kimberly-Clark Worldwide, Inc. | Multicomponent biodegradable filaments and nonwoven webs formed therefrom |
| CN102046861B (zh) | 2008-05-30 | 2012-12-12 | 金伯利-克拉克环球有限公司 | 聚乳酸纤维 |
| US8927488B2 (en) | 2010-05-17 | 2015-01-06 | Cebix, Inc. | Pegylated C-peptide |
| US8461262B2 (en) | 2010-12-07 | 2013-06-11 | Kimberly-Clark Worldwide, Inc. | Polylactic acid fibers |
| EP2559435A1 (en) | 2011-08-19 | 2013-02-20 | UCB Pharma GmbH | Rotigotine in the treatment of hemispatial neglect, stroke and deficits following stroke |
| US20130315891A1 (en) | 2012-05-25 | 2013-11-28 | Matthew Charles | Formulations of human tissue kallikrein-1 for parenteral delivery and related methods |
| SI2854841T1 (sl) | 2012-06-04 | 2017-06-30 | Diamedica Inc. | Glikozilacijske izooblike humanega tkivnega kalikreina-1 |
| DE102014005782A1 (de) * | 2014-04-23 | 2015-10-29 | Martin-Luther-Universität Halle-Wittenberg | lnjizierbare und implantierbare Trägersysteme auf Basis von modifizierten Poly(dikarbonsäure-multiol estern) zur kontrollierten Wirkstofffreisetzung |
| CA3054962A1 (en) | 2017-03-09 | 2018-09-13 | Rick PAULS | Dosage forms of tissue kallikrein 1 |
| EP4653449A1 (en) * | 2023-02-08 | 2025-11-26 | Spiber Inc. | Method for producing block copolymer or aqueous dispersion containing same, adhesive, coating liquid, coating agent, or molded body |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5929196A (en) * | 1994-02-25 | 1999-07-27 | Schwarz Pharma Ag | Polyesters of a polyhydroxycarboxylic acid and a polyol having a substituent with electrolyte properties |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3773919A (en) | 1969-10-23 | 1973-11-20 | Du Pont | Polylactide-drug mixtures |
| IE52535B1 (en) | 1981-02-16 | 1987-12-09 | Ici Plc | Continuous release pharmaceutical compositions |
| ATE37983T1 (de) | 1982-04-22 | 1988-11-15 | Ici Plc | Mittel mit verzoegerter freigabe. |
| CH656884A5 (de) | 1983-08-26 | 1986-07-31 | Sandoz Ag | Polyolester, deren herstellung und verwendung. |
| US4726076A (en) | 1985-06-26 | 1988-02-23 | Francoise Douez | Childs garment |
| JPH0613602B2 (ja) | 1987-07-14 | 1994-02-23 | 三井東圧化学株式会社 | ｄ▲ｌ▼−乳酸−グリコール酸共重合物の製造方法 |
| ATE188976T1 (de) | 1988-11-01 | 2000-02-15 | Boehringer Ingelheim Pharma | Kontinuierliches verfahren zur herstellung von resorbierbaren polyestern und deren verwendung |
| WO1990008793A1 (en) | 1989-01-27 | 1990-08-09 | Mitsui Toatsu Chemicals, Inc. | Biocompatible polyester and production thereof |
| JP3307777B2 (ja) * | 1994-07-07 | 2002-07-24 | 栄修 永田 | ハンダ付け方法および装置 |
| US6046882A (en) * | 1996-07-11 | 2000-04-04 | International Business Machines Corporation | Solder balltape and method for making electrical connection between a head transducer and an electrical lead |
| US6595408B1 (en) * | 1998-10-07 | 2003-07-22 | Micron Technology, Inc. | Method of attaching solder balls to BGA package utilizing a tool to pick and dip the solder ball in flux prior to placement |
| US6336581B1 (en) * | 2000-06-19 | 2002-01-08 | International Business Machines Corporation | Solder ball connection device and capillary tube thereof |
| JP2002025025A (ja) * | 2000-06-23 | 2002-01-25 | Internatl Business Mach Corp <Ibm> | はんだボール接合装置及びはんだボール接合方法 |
| US6589594B1 (en) * | 2000-08-31 | 2003-07-08 | Micron Technology, Inc. | Method for filling a wafer through-via with a conductive material |
| JP2002251705A (ja) * | 2001-02-16 | 2002-09-06 | Internatl Business Mach Corp <Ibm> | はんだボール配設装置、はんだボールリフロー装置、及びはんだボール接合装置。 |
| DE10132567B4 (de) * | 2001-07-10 | 2005-03-31 | Pac Tech - Packaging Technologies Gmbh | Verfahren und Vorrichtung zum Aufbringen eines Lötmittels auf ein Substrat |
| JP3753968B2 (ja) * | 2001-10-11 | 2006-03-08 | ヒタチグローバルストレージテクノロジーズネザーランドビーブイ | 配線一体型サスペンション及びその製造方法 |
| JP4212992B2 (ja) * | 2003-09-03 | 2009-01-21 | Ｔｄｋ株式会社 | 半田ボールの供給方法および供給装置 |
-
2000
- 2000-11-10 DE DE10055742A patent/DE10055742B4/de not_active Expired - Fee Related
-
2001
- 2001-11-08 US US10/416,472 patent/US7087247B2/en not_active Expired - Fee Related
- 2001-11-08 EP EP01990396A patent/EP1345979B1/de not_active Expired - Lifetime
- 2001-11-08 WO PCT/EP2001/012888 patent/WO2002038646A2/de not_active Ceased
- 2001-11-08 JP JP2002541975A patent/JP2004514002A/ja active Pending
- 2001-11-08 AU AU2002229539A patent/AU2002229539A1/en not_active Abandoned
- 2001-11-08 ES ES01990396T patent/ES2225636T3/es not_active Expired - Lifetime
- 2001-11-08 DE DE50102886T patent/DE50102886D1/de not_active Expired - Lifetime
- 2001-11-08 AT AT01990396T patent/ATE271083T1/de not_active IP Right Cessation
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5929196A (en) * | 1994-02-25 | 1999-07-27 | Schwarz Pharma Ag | Polyesters of a polyhydroxycarboxylic acid and a polyol having a substituent with electrolyte properties |
Also Published As
| Publication number | Publication date |
|---|---|
| US20040072986A1 (en) | 2004-04-15 |
| EP1345979A2 (de) | 2003-09-24 |
| US7087247B2 (en) | 2006-08-08 |
| ATE271083T1 (de) | 2004-07-15 |
| EP1345979B1 (de) | 2004-07-14 |
| WO2002038646A2 (de) | 2002-05-16 |
| DE10055742A1 (de) | 2002-05-29 |
| DE50102886D1 (de) | 2004-08-19 |
| JP2004514002A (ja) | 2004-05-13 |
| WO2002038646A3 (de) | 2002-08-01 |
| ES2225636T3 (es) | 2005-03-16 |
| AU2002229539A1 (en) | 2002-05-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OP8 | Request for examination as to paragraph 44 patent law | ||
| 8339 | Ceased/non-payment of the annual fee |