ZA200202695B - Manufacture of polyglutamate-therapeutic agent conjugates. - Google Patents
Manufacture of polyglutamate-therapeutic agent conjugates. Download PDFInfo
- Publication number
- ZA200202695B ZA200202695B ZA200202695A ZA200202695A ZA200202695B ZA 200202695 B ZA200202695 B ZA 200202695B ZA 200202695 A ZA200202695 A ZA 200202695A ZA 200202695 A ZA200202695 A ZA 200202695A ZA 200202695 B ZA200202695 B ZA 200202695B
- Authority
- ZA
- South Africa
- Prior art keywords
- conjugate
- acid
- therapeutic agent
- poly
- polyglutamic acid
- Prior art date
Links
- 239000003814 drug Substances 0.000 title claims description 75
- 229940124597 therapeutic agent Drugs 0.000 title claims description 70
- 238000004519 manufacturing process Methods 0.000 title claims description 12
- 229920002643 polyglutamic acid Polymers 0.000 claims description 89
- 239000000243 solution Substances 0.000 claims description 69
- 238000000034 method Methods 0.000 claims description 66
- 229960001592 paclitaxel Drugs 0.000 claims description 59
- 108010020346 Polyglutamic Acid Proteins 0.000 claims description 49
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 42
- 239000007787 solid Substances 0.000 claims description 39
- 229920000642 polymer Polymers 0.000 claims description 37
- 230000008569 process Effects 0.000 claims description 36
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 27
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- GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 description 1
- GCSAXWHQFYOIFE-UHFFFAOYSA-N dipyridin-2-yl carbonate Chemical compound C=1C=CC=NC=1OC(=O)OC1=CC=CC=N1 GCSAXWHQFYOIFE-UHFFFAOYSA-N 0.000 description 1
- UZUODNWWWUQRIR-UHFFFAOYSA-L disodium;3-aminonaphthalene-1,5-disulfonate Chemical compound [Na+].[Na+].C1=CC=C(S([O-])(=O)=O)C2=CC(N)=CC(S([O-])(=O)=O)=C21 UZUODNWWWUQRIR-UHFFFAOYSA-L 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 230000007247 enzymatic mechanism Effects 0.000 description 1
- 238000006911 enzymatic reaction Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 150000001261 hydroxy acids Chemical class 0.000 description 1
- 238000002513 implantation Methods 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- JDNTWHVOXJZDSN-UHFFFAOYSA-N iodoacetic acid Chemical compound OC(=O)CI JDNTWHVOXJZDSN-UHFFFAOYSA-N 0.000 description 1
- 229960000310 isoleucine Drugs 0.000 description 1
- AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 238000005007 materials handling Methods 0.000 description 1
- 231100000682 maximum tolerated dose Toxicity 0.000 description 1
- HNEGQIOMVPPMNR-NSCUHMNNSA-N mesaconic acid Chemical compound OC(=O)C(/C)=C/C(O)=O HNEGQIOMVPPMNR-NSCUHMNNSA-N 0.000 description 1
- HNEGQIOMVPPMNR-UHFFFAOYSA-N methylfumaric acid Natural products OC(=O)C(C)=CC(O)=O HNEGQIOMVPPMNR-UHFFFAOYSA-N 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 238000000569 multi-angle light scattering Methods 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 230000008634 non enzymatic mechanism Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 239000013618 particulate matter Substances 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical class C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000011833 salt mixture Substances 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000001374 small-angle light scattering Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- 150000003754 zirconium Chemical class 0.000 description 1
Classifications
-
- 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
- A61K47/50—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
-
- 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
- A61K47/50—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
- A61K47/51—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
- A61K47/62—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 a protein, peptide or polyamino acid
- A61K47/64—Drug-peptide, drug-protein or drug-polyamino acid conjugates, i.e. the modifying agent being a peptide, protein or polyamino acid which is covalently bonded or complexed to a therapeutically active agent
- A61K47/645—Polycationic or polyanionic oligopeptides, polypeptides or polyamino acids, e.g. polylysine, polyarginine, polyglutamic acid or peptide TAT
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Epidemiology (AREA)
- Molecular Biology (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Polyamides (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US15913599P | 1999-10-12 | 1999-10-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200202695B true ZA200202695B (en) | 2004-02-25 |
Family
ID=22571222
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200202695A ZA200202695B (en) | 1999-10-12 | 2002-04-05 | Manufacture of polyglutamate-therapeutic agent conjugates. |
Country Status (16)
| Country | Link |
|---|---|
| US (2) | US20020077279A1 (enExample) |
| EP (2) | EP1466627A1 (enExample) |
| JP (1) | JP2003511423A (enExample) |
| KR (1) | KR100821437B1 (enExample) |
| CN (2) | CN101507820A (enExample) |
| AU (1) | AU781735B2 (enExample) |
| BR (1) | BRPI0014652B1 (enExample) |
| CA (1) | CA2387611C (enExample) |
| HU (1) | HUP0203123A3 (enExample) |
| MX (1) | MXPA02003719A (enExample) |
| NO (1) | NO20021701L (enExample) |
| NZ (1) | NZ529789A (enExample) |
| PL (1) | PL354623A1 (enExample) |
| SG (1) | SG147286A1 (enExample) |
| WO (1) | WO2001026693A2 (enExample) |
| ZA (1) | ZA200202695B (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1294404A2 (en) | 2000-06-14 | 2003-03-26 | Corixa Corporation | Prodrug compounds with an oligopeptide having an isoleucine residue |
| US6872715B2 (en) | 2001-08-06 | 2005-03-29 | Kosan Biosciences, Inc. | Benzoquinone ansamycins |
| WO2004093807A2 (en) | 2003-04-22 | 2004-11-04 | Societe De Conseils De Recherches Et D'applications Scientifiques S.A.S. | Somatostatin vectors |
| FR2855521B1 (fr) * | 2003-05-28 | 2005-08-05 | Flamel Tech Sa | Polyaminoacides fonctionnalises par au moins un groupement h ydrophobe et leurs applications notamment therapeutiques. |
| US7259156B2 (en) | 2004-05-20 | 2007-08-21 | Kosan Biosciences Incorporated | Geldanamycin compounds and method of use |
| WO2006020722A2 (en) | 2004-08-11 | 2006-02-23 | Arqule, Inc. | Polymer conjugates of beta-lapachone and beta-lapachone analogs for tumor targeting |
| US8614228B2 (en) | 2004-08-11 | 2013-12-24 | Arqule, Inc. | Quinone prodrug compositions and methods of use |
| PL1792927T3 (pl) | 2004-09-22 | 2013-09-30 | Nippon Kayaku Kk | Nowy kopolimer blokowy, preparat micelarny i lek przeciwnowotworowy zawierający ten preparat micelarny jako składnik czynny |
| RU2472812C2 (ru) | 2005-12-05 | 2013-01-20 | НИТТО ДЕНКО КОРПОРЭЙШН (Джэпэн/Джэпэн) | Конъюгаты полиглутамат-аминокислота и способы |
| KR20080074202A (ko) * | 2005-12-06 | 2008-08-12 | 셀 쎄러퓨틱스 인코포레이티드 | 에스트로겐 암 요법 |
| US7462627B2 (en) * | 2006-02-09 | 2008-12-09 | Enzon Pharmaceuticals, Inc. | Multi-arm polymeric conjugates of 7-ethyl-10-hydroxycamptothecin for treatment of breast, colorectal, pancreatic, ovarian and lung cancers |
| US7671067B2 (en) * | 2006-02-09 | 2010-03-02 | Enzon Pharmaceuticals, Inc. | Treatment of non-hodgkin's lymphomas with multi-arm polymeric conjugates of 7-ethyl-10-hydroxycamtothecin |
| JP5249016B2 (ja) | 2006-03-28 | 2013-07-31 | 日本化薬株式会社 | タキサン類の高分子結合体 |
| KR20090009241A (ko) | 2006-05-18 | 2009-01-22 | 니폰 가야꾸 가부시끼가이샤 | 포도필로톡신류의 고분자 결합체 |
| EP2080779B1 (en) | 2006-11-06 | 2016-05-18 | Nippon Kayaku Kabushiki Kaisha | Polymeric derivative of nucleic acid metabolic antagonist |
| WO2008056654A1 (fr) | 2006-11-08 | 2008-05-15 | Nippon Kayaku Kabushiki Kaisha | Dérivé polymère d'un antagoniste métabolique d'acide nucléique |
| CN101209350B (zh) * | 2006-12-30 | 2011-09-07 | 中国人民解放军军事医学科学院毒物药物研究所 | 以氨基酸为连接子的多聚谷氨酸-药物偶合物 |
| KR20090108082A (ko) * | 2007-02-09 | 2009-10-14 | 엔존 파마슈티컬즈, 인코포레이티드 | 7-에틸-10-하이드록시캄토테신 다분지형 고분자 접합체를 이용한 내성 또는 불응성 암의 치료방법 |
| CN101674852A (zh) * | 2007-04-10 | 2010-03-17 | 日东电工株式会社 | 多功能聚谷氨酸盐药物载体 |
| US7790765B2 (en) | 2007-04-30 | 2010-09-07 | Arqule, Inc. | Hydroxy sulfonate of quinone compounds and their uses |
| DK2155254T3 (da) * | 2007-05-09 | 2013-03-04 | Nitto Denko Corp | Med platinlægemidler konjugerede polymere |
| JP5341879B2 (ja) * | 2007-05-09 | 2013-11-13 | 日東電工株式会社 | 疎水性化合物及びポリアミノ酸複合体を含む組成物 |
| JP2010526917A (ja) * | 2007-05-09 | 2010-08-05 | 日東電工株式会社 | 複数種の薬物を有するポリグルタミン酸塩複合体及びポリグルタミン酸塩−アミノ酸複合体 |
| USRE46190E1 (en) | 2007-09-28 | 2016-11-01 | Nippon Kayaku Kabushiki Kaisha | High-molecular weight conjugate of steroids |
| EP2262537A1 (en) * | 2008-03-06 | 2010-12-22 | Nitto Denko Corporation | Polymer paclitaxel conjugates and methods for treating cancer |
| JP5687899B2 (ja) | 2008-03-18 | 2015-03-25 | 日本化薬株式会社 | 生理活性物質の高分子結合体 |
| US9149540B2 (en) | 2008-05-08 | 2015-10-06 | Nippon Kayaku Kabushiki Kaisha | Polymer conjugate of folic acid or folic acid derivative |
| TW201010732A (en) * | 2008-08-29 | 2010-03-16 | Enzon Pharmaceuticals Inc | Method of treating RAS associated cancer |
| KR101705077B1 (ko) * | 2008-10-07 | 2017-02-09 | 렉산 파마슈티컬스, 인코포레이티드 | Ｈｐｍａ-도세탁셀 또는 젬시타빈 컨쥬게이트 및 이의 용도 |
| US20100093935A1 (en) * | 2008-10-15 | 2010-04-15 | Nitto Denko Corporation | Method of preparing polyglutamate conjugates |
| KR20110075029A (ko) * | 2008-10-21 | 2011-07-05 | 엔즌 파마슈티칼스, 인코포레이티드 | 7-에틸-10-하이드록시캄토테신의 다중-암 고분자 컨쥬게이트로 신경모세포종의 치료 |
| DE102008060549A1 (de) * | 2008-12-04 | 2010-06-10 | MAX-PLANCK-Gesellschaft zur Förderung der Wissenschaften e.V. | Wirkstoff-Peptid-Konstrukt zur extrazellulären Anreicherung |
| EP2431403B1 (en) | 2009-05-15 | 2016-09-28 | Nipponkayaku Kabushikikaisha | Polymer conjugate of bioactive substance having hydroxy group |
| EP2488207A4 (en) | 2009-10-13 | 2015-06-10 | Rexahn Pharmaceuticals Inc | POLYMERIC ANTIBODY RELEASE SYSTEMS |
| AU2011224374A1 (en) * | 2010-03-11 | 2012-09-27 | Nitto Denko Corporation | Carbohydrate-polyamino acid-drug conjugates |
| EP3372617B1 (en) | 2010-04-02 | 2024-07-24 | Amunix Pharmaceuticals, Inc. | Binding fusion proteins, binding fusion protein-drug conjugates, xten-drug conjugates and methods of making and using same |
| TW201304805A (zh) | 2010-11-17 | 2013-02-01 | Nippon Kayaku Kk | 新穎之胞核苷系代謝拮抗劑之高分子衍生物 |
| CN102649810A (zh) * | 2011-05-19 | 2012-08-29 | 东北林业大学 | 喜树碱衍生物、其制备方法和用途 |
| US8691284B2 (en) | 2011-07-07 | 2014-04-08 | Empire Technology Development Llc | Fluorinated block co-polymers |
| ES2635117T3 (es) | 2011-09-11 | 2017-10-02 | Nippon Kayaku Kabushiki Kaisha | Método para la fabricación de un copolímero de bloques |
| US8383093B1 (en) | 2011-11-01 | 2013-02-26 | Serina Therapeutics, Inc. | Subcutaneous delivery of poly(oxazoline) conjugates |
| US8907045B2 (en) | 2012-04-03 | 2014-12-09 | Empire Technology Development Llc | Biocompatible adhesive polymers |
| US9839694B2 (en) | 2013-04-26 | 2017-12-12 | Nitto Denko Corporation | Reduction of endotoxins from polyanionic polymer conjugates |
| KR101507119B1 (ko) * | 2013-05-31 | 2015-03-30 | 주식회사 바이오리더스 | 점막 점착성 폴리감마글루탐산 나노마이셀 및 이를 이용한 약물 전달체 |
| CN106267227A (zh) * | 2016-08-12 | 2017-01-04 | 北京蓝贝望生物医药科技股份有限公司 | 抗肿瘤药物 |
| CN106750272B (zh) * | 2016-12-05 | 2019-05-28 | 福建卫生职业技术学院 | 一种水溶性蛇葡萄素聚合物 |
| CN110123748A (zh) * | 2019-04-22 | 2019-08-16 | 南京师范大学 | 一种叶酸介导的靶向双载药聚合物胶束及其制备方法和应用 |
| CN113773282A (zh) * | 2021-09-22 | 2021-12-10 | 无锡紫杉药业有限公司 | 一种10-乙酰紫杉醇的制备方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4356166A (en) * | 1978-12-08 | 1982-10-26 | University Of Utah | Time-release chemical delivery system |
| US5629433A (en) * | 1994-07-18 | 1997-05-13 | Hauser, Inc. | Selective process for the deacylation and deacetylation of taxol and taxanes |
| CA2192725C (en) * | 1995-12-28 | 2004-04-20 | Kenji Tsujihara | Camptothecin derivatives |
| US6441025B2 (en) * | 1996-03-12 | 2002-08-27 | Pg-Txl Company, L.P. | Water soluble paclitaxel derivatives |
| EP0932399B1 (en) * | 1996-03-12 | 2006-01-04 | PG-TXL Company, L.P. | Water soluble paclitaxel prodrugs |
| CA2402643A1 (en) * | 2000-03-17 | 2001-09-27 | Cell Therapeutics, Inc. | Polyglutamic acid-camptothecin conjugates and methods of preparation |
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2000
- 2000-10-12 CA CA2387611A patent/CA2387611C/en not_active Expired - Fee Related
- 2000-10-12 AU AU10793/01A patent/AU781735B2/en not_active Ceased
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- 2000-10-12 JP JP2001529754A patent/JP2003511423A/ja active Pending
- 2000-10-12 SG SG200401981-6A patent/SG147286A1/en unknown
- 2000-10-12 EP EP04013703A patent/EP1466627A1/en not_active Withdrawn
- 2000-10-12 BR BRPI0014652A patent/BRPI0014652B1/pt not_active IP Right Cessation
- 2000-10-12 HU HU0203123A patent/HUP0203123A3/hu unknown
- 2000-10-12 NZ NZ529789A patent/NZ529789A/en not_active IP Right Cessation
- 2000-10-12 CN CNA2009101276554A patent/CN101507820A/zh active Pending
- 2000-10-12 PL PL00354623A patent/PL354623A1/xx not_active IP Right Cessation
- 2000-10-12 KR KR1020027004640A patent/KR100821437B1/ko not_active Expired - Fee Related
- 2000-10-12 WO PCT/US2000/028109 patent/WO2001026693A2/en not_active Ceased
- 2000-10-12 EP EP00972079A patent/EP1225917A2/en not_active Withdrawn
- 2000-10-12 CN CNA008170290A patent/CN1607962A/zh active Pending
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2001
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2002
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- 2002-04-11 NO NO20021701A patent/NO20021701L/no not_active Application Discontinuation
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2003
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Also Published As
| Publication number | Publication date |
|---|---|
| US7399860B2 (en) | 2008-07-15 |
| KR20020059616A (ko) | 2002-07-13 |
| US20020077279A1 (en) | 2002-06-20 |
| HUP0203123A3 (en) | 2004-12-28 |
| KR100821437B1 (ko) | 2008-04-10 |
| CN101507820A (zh) | 2009-08-19 |
| PL354623A1 (en) | 2004-02-09 |
| HUP0203123A2 (hu) | 2003-01-28 |
| NO20021701L (no) | 2002-05-23 |
| EP1466627A1 (en) | 2004-10-13 |
| WO2001026693A2 (en) | 2001-04-19 |
| AU781735B2 (en) | 2005-06-09 |
| SG147286A1 (en) | 2008-11-28 |
| CA2387611C (en) | 2011-03-29 |
| US20030224971A1 (en) | 2003-12-04 |
| WO2001026693A3 (en) | 2001-12-27 |
| CA2387611A1 (en) | 2001-04-19 |
| EP1225917A2 (en) | 2002-07-31 |
| MXPA02003719A (es) | 2002-08-30 |
| NZ529789A (en) | 2005-04-29 |
| BR0014652A (pt) | 2003-06-10 |
| NO20021701D0 (no) | 2002-04-11 |
| BRPI0014652B1 (pt) | 2016-08-09 |
| AU1079301A (en) | 2001-04-23 |
| CN1607962A (zh) | 2005-04-20 |
| JP2003511423A (ja) | 2003-03-25 |
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