SK145598A3 - Sustained release ionic conjugate - Google Patents
Sustained release ionic conjugate Download PDFInfo
- Publication number
- SK145598A3 SK145598A3 SK1455-98A SK145598A SK145598A3 SK 145598 A3 SK145598 A3 SK 145598A3 SK 145598 A SK145598 A SK 145598A SK 145598 A3 SK145598 A3 SK 145598A3
- Authority
- SK
- Slovakia
- Prior art keywords
- liquid
- conjugate
- solution
- biodegradable polymer
- acid
- Prior art date
Links
- 238000013268 sustained release Methods 0.000 title abstract description 3
- 239000012730 sustained-release form Substances 0.000 title abstract description 3
- 238000000034 method Methods 0.000 claims abstract description 55
- 239000003814 drug Substances 0.000 claims abstract description 42
- 239000004621 biodegradable polymer Substances 0.000 claims abstract description 37
- 229920002988 biodegradable polymer Polymers 0.000 claims abstract description 37
- 229940079593 drug Drugs 0.000 claims abstract description 23
- 125000003277 amino group Chemical group 0.000 claims abstract description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 9
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- 239000011859 microparticle Substances 0.000 claims description 37
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- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims description 31
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 29
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 29
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- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
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- A61K9/1641—Organic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyethylene glycol, poloxamers
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- A61K38/17—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
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- A61K47/50—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
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- A61K47/59—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyureas or polyurethanes
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- A61K47/69—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit
- A61K47/6921—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit the form being a particulate, a powder, an adsorbate, a bead or a sphere
- A61K47/6927—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit the form being a particulate, a powder, an adsorbate, a bead or a sphere the form being a solid microparticle having no hollow or gas-filled cores
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- 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
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- A—HUMAN NECESSITIES
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- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
- A61K9/167—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction with an outer layer or coating comprising drug; with chemically bound drugs or non-active substances on their surface
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- 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
- A61K9/1682—Processes
- A61K9/1694—Processes resulting in granules or microspheres of the matrix type containing more than 5% of excipient
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2982—Particulate matter [e.g., sphere, flake, etc.]
- Y10T428/2984—Microcapsule with fluid core [includes liposome]
- Y10T428/2985—Solid-walled microcapsule from synthetic polymer
Landscapes
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Gastroenterology & Hepatology (AREA)
- Immunology (AREA)
- Endocrinology (AREA)
- Zoology (AREA)
- Medicinal Preparation (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cosmetics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Steroid Compounds (AREA)
- Crystals, And After-Treatments Of Crystals (AREA)
- Saccharide Compounds (AREA)
- Manufacturing Of Micro-Capsules (AREA)
- Lubricants (AREA)
- Fire-Extinguishing Compositions (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Detergent Compositions (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
IE960308A IE960308A1 (en) | 1996-04-23 | 1996-04-23 | Sustained release ionic conjugate |
PCT/IE1997/000030 WO1997039738A2 (en) | 1996-04-23 | 1997-04-22 | Sustained release ionic conjugate |
Publications (1)
Publication Number | Publication Date |
---|---|
SK145598A3 true SK145598A3 (en) | 1999-03-12 |
Family
ID=11041150
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
SK1455-98A SK145598A3 (en) | 1996-04-23 | 1997-04-22 | Sustained release ionic conjugate |
Country Status (28)
Country | Link |
---|---|
US (3) | US6911218B2 (is) |
EP (1) | EP0904062B1 (is) |
JP (2) | JP3390177B2 (is) |
KR (1) | KR20000010621A (is) |
CN (2) | CN1186012C (is) |
AT (1) | ATE245970T1 (is) |
BG (1) | BG102947A (is) |
BR (1) | BR9708818A (is) |
CA (1) | CA2252826A1 (is) |
CZ (2) | CZ293965B6 (is) |
DE (1) | DE69723833T2 (is) |
DK (1) | DK0904062T3 (is) |
EE (1) | EE9800349A (is) |
ES (1) | ES2200172T3 (is) |
HK (1) | HK1018748A1 (is) |
HU (1) | HU224036B1 (is) |
IE (1) | IE960308A1 (is) |
IL (1) | IL126619A (is) |
IS (1) | IS4869A (is) |
NO (1) | NO984924L (is) |
NZ (1) | NZ332893A (is) |
PL (2) | PL189319B1 (is) |
PT (1) | PT904062E (is) |
RU (1) | RU2173137C2 (is) |
SK (1) | SK145598A3 (is) |
TR (1) | TR199802125T2 (is) |
WO (1) | WO1997039738A2 (is) |
YU (1) | YU46598A (is) |
Families Citing this family (36)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6221958B1 (en) * | 1993-01-06 | 2001-04-24 | Societe De Conseils De Recherches Et D'applications Scientifiques, Sas | Ionic molecular conjugates of biodegradable polyesters and bioactive polypeptides |
US6413539B1 (en) * | 1996-10-31 | 2002-07-02 | Poly-Med, Inc. | Hydrogel-forming, self-solvating absorbable polyester copolymers, and methods for use thereof |
IE960308A1 (en) * | 1996-04-23 | 1997-11-05 | Kinerton Ltd | Sustained release ionic conjugate |
US6867181B1 (en) | 1997-06-02 | 2005-03-15 | Societe De Conseils De Recherches Et D'applications Scientifiques, S.A.S. | Ionic molecular conjugates of biodegradable polyesters and bioactive polypeptides |
US6468519B1 (en) | 1997-09-10 | 2002-10-22 | Rutgers, The State University Of New Jersey | Polyanhydrides with biologically active degradation products |
US7122615B1 (en) | 1998-09-10 | 2006-10-17 | Rutgers, The State University Of New Jersey | Polyanhydrides with therapeutically useful degradation products |
US6486214B1 (en) | 1997-09-10 | 2002-11-26 | Rutgers, The State University Of New Jersey | Polyanhydride linkers for production of drug polymers and drug polymer compositions produced thereby |
EP1240896A3 (en) * | 1998-07-23 | 2003-03-26 | Societe De Conseils De Recherches Et D'applications Scientifiques S.A.S. | Encapsulation of water soluble peptides |
US7109166B1 (en) | 1999-08-18 | 2006-09-19 | Societe De Conseils De Recherches Et D'applications Scientifiques, Sas | Sustained release formulation of a peptide |
DE60027334T2 (de) * | 1999-08-18 | 2007-03-29 | Société de Conseils de Recherches et d'Applications Scientifiques S.A.S. | Zusammensetzung mit verzögerter Abgabe in der ein Peptid mit einem Polymer komplexiert ist |
EP1348444B1 (en) * | 1999-08-18 | 2006-04-12 | Societe De Conseils De Recherches Et D'applications Scientifiques S.A.S. | Sustained release formulation of a peptide complexed with a polymer |
IES990700A2 (en) | 1999-08-18 | 2001-08-22 | Kinerton Ltd | Process to make a sustained release formulation |
US6685928B2 (en) | 1999-12-07 | 2004-02-03 | Rutgers, The State University Of New Jersey | Therapeutic compositions and methods |
US20040038948A1 (en) | 1999-12-07 | 2004-02-26 | Uhrich Kathryn E. | Therapeutic compositions and methods |
KR100452752B1 (ko) * | 2000-04-18 | 2004-10-12 | 주식회사 펩트론 | 단백질 함유 서방성 제제를 제조하는 방법 및 그 제제 |
CA2771263A1 (en) | 2000-07-27 | 2002-02-07 | Rutgers, The State University | Therapeutic polyesters and polyamides |
US6602915B2 (en) | 2000-07-27 | 2003-08-05 | Rutgers, The State University Of New Jersey | Therapeutic azo-compounds for drug delivery |
JP2005523265A (ja) | 2002-02-07 | 2005-08-04 | ラットガーズ,ザ・ステート・ユニバーシティ・オブ・ニュージャージー | 治療用ポリエステルおよびポリアミド |
EP1499367A1 (en) * | 2002-04-24 | 2005-01-26 | Poly-Med, Inc. | Multifaceted endovascular stent coating for preventing restenosis |
JP4723859B2 (ja) * | 2002-12-04 | 2011-07-13 | 日本曹達株式会社 | Oil/Oil液中乾燥法による農薬マイクロカプセル製剤及びその製造方法 |
KR101242543B1 (ko) | 2004-10-27 | 2013-03-22 | 유니버시티 오브 덴버 | 부신피질 자극 호르몬 유사체 및 관련 방법 |
EP1951260A4 (en) | 2005-10-21 | 2009-11-11 | Bezwada Biomedical Llc | FUNCTIONALIZED PHENOLIC COMPOUNDS AND POURABLE ARTICLES THEREOF |
US8007526B2 (en) | 2005-12-01 | 2011-08-30 | Bezwada Biomedical, Llc | Difunctionalized aromatic compounds and polymers therefrom |
EP2102144A4 (en) | 2006-09-13 | 2011-03-23 | Univ Rutgers | ACTIVE SUBSTANCES AND THEIR OLIGOMERS AND POLYMERS |
EP2148691B1 (en) | 2007-02-05 | 2015-05-20 | Apellis Pharmaceuticals, Inc. | Compstatin analogues for use in the treatment of inflammatory conditions of the respiratory system |
AR066677A1 (es) * | 2007-05-24 | 2009-09-02 | Novartis Ag | Formulacion de pasireotida. composicion farmaceutica para liberacion prolongada. microparticulas. |
US8217134B2 (en) | 2007-08-30 | 2012-07-10 | Bezwada Biomedical, Llc | Controlled release of biologically active compounds |
US8048980B2 (en) | 2007-09-17 | 2011-11-01 | Bezwada Biomedical, Llc | Hydrolysable linkers and cross-linkers for absorbable polymers |
KR101224004B1 (ko) * | 2009-12-29 | 2013-01-22 | 주식회사 삼양바이오팜 | 단백질, 폴리펩타이드 또는 펩타이드 약물 전달용 고분자 및 그 제조방법, 및 단백질, 폴리펩타이드 또는 펩타이드 약물의 서방형 조성물 및 그 제조 방법 |
US9144579B2 (en) | 2012-08-17 | 2015-09-29 | Rutgers, The State University Of New Jersey | Polyesters and methods of use thereof |
US20140120057A1 (en) | 2012-10-25 | 2014-05-01 | Rutgers, The State University Of New Jersey | Polymers and methods thereof for wound healing |
US9387250B2 (en) | 2013-03-15 | 2016-07-12 | Rutgers, The State University Of New Jersey | Therapeutic compositions for bone repair |
US9862672B2 (en) | 2013-05-29 | 2018-01-09 | Rutgers, The State University Of New Jersey | Antioxidant-based poly(anhydride-esters) |
WO2015191742A1 (en) | 2014-06-13 | 2015-12-17 | Rutgers, The State University Of New Jersey | Process and intermediates for preparing poly(anhydride-esters) |
TW201618783A (zh) | 2014-08-07 | 2016-06-01 | 艾森塔製藥公司 | 以布魯頓(Bruton)氏酪胺酸激酶(BTK)佔據和BTK再合成速率為基礎之治療癌症、免疫和自體免疫疾病及發炎性疾病之方法 |
JP6930918B6 (ja) | 2015-04-10 | 2021-12-15 | ラトガーズ, ザ ステイト ユニバーシティ オブ ニュー ジャージー | コウジ酸ポリマー |
Family Cites Families (15)
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 |
JPS5933214A (ja) | 1982-08-19 | 1984-02-23 | Mitsui Toatsu Chem Inc | 微小球に製剤された制ガン剤の製造方法 |
DE3936191C2 (de) | 1989-10-31 | 1996-10-17 | Boehringer Ingelheim Kg | Neue Copolymere aus Milchsäure und Weinsäure, ihre Herstellung sowie ihre Verwendung |
JP2653255B2 (ja) | 1990-02-13 | 1997-09-17 | 武田薬品工業株式会社 | 長期徐放型マイクロカプセル |
MY107937A (en) | 1990-02-13 | 1996-06-29 | Takeda Chemical Industries Ltd | Prolonged release microcapsules. |
DE4034334A1 (de) | 1990-10-29 | 1992-04-30 | Basf Ag | Verwendung von weinsaeure einkondensiert enthaltenden polyestern als waschmittelzusatz, verfahren zur herstellung der polyester und polyester aus weinsaeure und tetracarbonsaeuren |
ZA93929B (en) * | 1992-02-18 | 1993-09-10 | Akzo Nv | A process for the preparation of biologically active materialcontaining polymeric microcapsules. |
ATE154240T1 (de) * | 1992-03-12 | 1997-06-15 | Alkermes Inc | Acth enthaltende mikrokugeln mit gesteuerter abgabe |
AU4923793A (en) | 1992-09-22 | 1994-04-12 | Biopak Technology, Ltd. | Degradation control of environmentally degradable disposable materials |
EP0678018B1 (en) * | 1993-01-06 | 2003-04-09 | Kinerton Limited | Ionic molecular conjugates of biodegradable polyesters and bioactive polypeptides |
US6221958B1 (en) | 1993-01-06 | 2001-04-24 | Societe De Conseils De Recherches Et D'applications Scientifiques, Sas | Ionic molecular conjugates of biodegradable polyesters and bioactive polypeptides |
GB9310030D0 (en) | 1993-05-15 | 1993-06-30 | Scras | Dry processed particles and process for the preparation of the same |
IE960308A1 (en) * | 1996-04-23 | 1997-11-05 | Kinerton Ltd | Sustained release ionic conjugate |
AU727340C (en) | 1996-04-23 | 2001-11-08 | Ipsen Manufacturing Ireland Limited | Acidic polylactic polymers |
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1996
- 1996-04-23 IE IE960308A patent/IE960308A1/en not_active IP Right Cessation
-
1997
- 1997-04-22 PL PL97329606A patent/PL189319B1/pl not_active IP Right Cessation
- 1997-04-22 AT AT97917391T patent/ATE245970T1/de not_active IP Right Cessation
- 1997-04-22 BR BR9708818-8A patent/BR9708818A/pt unknown
- 1997-04-22 PT PT97917391T patent/PT904062E/pt unknown
- 1997-04-22 DK DK97917391T patent/DK0904062T3/da active
- 1997-04-22 CA CA002252826A patent/CA2252826A1/en not_active Abandoned
- 1997-04-22 RU RU98121128/14A patent/RU2173137C2/ru not_active IP Right Cessation
- 1997-04-22 CZ CZ20031935A patent/CZ293965B6/cs not_active IP Right Cessation
- 1997-04-22 CN CNB971940673A patent/CN1186012C/zh not_active Expired - Fee Related
- 1997-04-22 KR KR1019980708520A patent/KR20000010621A/ko active Search and Examination
- 1997-04-22 IL IL12661997A patent/IL126619A/xx not_active IP Right Cessation
- 1997-04-22 US US09/171,740 patent/US6911218B2/en not_active Expired - Fee Related
- 1997-04-22 JP JP53789697A patent/JP3390177B2/ja not_active Expired - Fee Related
- 1997-04-22 ES ES97917391T patent/ES2200172T3/es not_active Expired - Lifetime
- 1997-04-22 EE EE9800349A patent/EE9800349A/xx unknown
- 1997-04-22 EP EP97917391A patent/EP0904062B1/en not_active Expired - Lifetime
- 1997-04-22 CN CNA2004100565427A patent/CN1626243A/zh active Pending
- 1997-04-22 PL PL97363455A patent/PL188517B1/pl not_active IP Right Cessation
- 1997-04-22 DE DE69723833T patent/DE69723833T2/de not_active Expired - Fee Related
- 1997-04-22 TR TR1998/02125T patent/TR199802125T2/xx unknown
- 1997-04-22 SK SK1455-98A patent/SK145598A3/sk unknown
- 1997-04-22 WO PCT/IE1997/000030 patent/WO1997039738A2/en active IP Right Grant
- 1997-04-22 HU HU0000122A patent/HU224036B1/hu not_active IP Right Cessation
- 1997-04-22 CZ CZ19983299A patent/CZ293822B6/cs not_active IP Right Cessation
- 1997-04-22 NZ NZ332893A patent/NZ332893A/xx unknown
-
1998
- 1998-10-16 IS IS4869A patent/IS4869A/is unknown
- 1998-10-22 NO NO984924A patent/NO984924L/no not_active Application Discontinuation
- 1998-10-22 YU YU46598A patent/YU46598A/sh unknown
- 1998-11-23 BG BG102947A patent/BG102947A/xx unknown
-
1999
- 1999-09-10 HK HK99103943A patent/HK1018748A1/xx not_active IP Right Cessation
-
2002
- 2002-07-03 JP JP2002195134A patent/JP2003026606A/ja active Pending
-
2003
- 2003-08-07 US US10/636,357 patent/US7026431B2/en not_active Expired - Fee Related
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2006
- 2006-01-19 US US11/335,283 patent/US7179490B2/en not_active Expired - Fee Related
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