MX9804119A - Analogos de antraciclina citotoxica dirigidos. - Google Patents
Analogos de antraciclina citotoxica dirigidos.Info
- Publication number
- MX9804119A MX9804119A MX9804119A MX9804119A MX9804119A MX 9804119 A MX9804119 A MX 9804119A MX 9804119 A MX9804119 A MX 9804119A MX 9804119 A MX9804119 A MX 9804119A MX 9804119 A MX9804119 A MX 9804119A
- Authority
- MX
- Mexico
- Prior art keywords
- deamino
- doxorubicin
- dox
- analogs
- moiety
- Prior art date
Links
- 229940045799 anthracyclines and related substance Drugs 0.000 title abstract 2
- 231100000433 cytotoxic Toxicity 0.000 title 1
- 230000001472 cytotoxic effect Effects 0.000 title 1
- 229960004679 doxorubicin Drugs 0.000 abstract 9
- AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 abstract 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- 102000005157 Somatostatin Human genes 0.000 abstract 2
- 108010056088 Somatostatin Proteins 0.000 abstract 2
- DNDCVAGJPBKION-DOPDSADYSA-N bombesin Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(N)=O)NC(=O)CNC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@H](CC=1NC2=CC=CC=C2C=1)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)CNC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H]1NC(=O)CC1)C(C)C)C1=CN=CN1 DNDCVAGJPBKION-DOPDSADYSA-N 0.000 abstract 2
- 239000000813 peptide hormone Substances 0.000 abstract 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 2
- 229920006395 saturated elastomer Chemical group 0.000 abstract 2
- 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 abstract 2
- 229960000553 somatostatin Drugs 0.000 abstract 2
- 150000000565 5-membered heterocyclic compounds Chemical class 0.000 abstract 1
- 150000000644 6-membered heterocyclic compounds Chemical class 0.000 abstract 1
- 108010051479 Bombesin Proteins 0.000 abstract 1
- 102000013585 Bombesin Human genes 0.000 abstract 1
- 101000904177 Clupea pallasii Gonadoliberin-1 Proteins 0.000 abstract 1
- 239000000579 Gonadotropin-Releasing Hormone Substances 0.000 abstract 1
- 101000904173 Homo sapiens Progonadoliberin-1 Proteins 0.000 abstract 1
- 206010028980 Neoplasm Diseases 0.000 abstract 1
- 102100024028 Progonadoliberin-1 Human genes 0.000 abstract 1
- 101000857870 Squalus acanthias Gonadoliberin Proteins 0.000 abstract 1
- 101000996723 Sus scrofa Gonadotropin-releasing hormone receptor Proteins 0.000 abstract 1
- 230000001093 anti-cancer Effects 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000002619 bicyclic group Chemical group 0.000 abstract 1
- KAKZBPTYRLMSJV-UHFFFAOYSA-N butadiene group Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- WPJRFCZKZXBUNI-HCWXCVPCSA-N daunosamine Chemical compound C[C@H](O)[C@@H](O)[C@@H](N)CC=O WPJRFCZKZXBUNI-HCWXCVPCSA-N 0.000 abstract 1
- XLXSAKCOAKORKW-UHFFFAOYSA-N gonadorelin Chemical compound C1CCC(C(=O)NCC(N)=O)N1C(=O)C(CCCN=C(N)N)NC(=O)C(CC(C)C)NC(=O)CNC(=O)C(NC(=O)C(CO)NC(=O)C(CC=1C2=CC=CC=C2NC=1)NC(=O)C(CC=1NC=NC=1)NC(=O)C1NC(=O)CC1)CC1=CC=C(O)C=C1 XLXSAKCOAKORKW-UHFFFAOYSA-N 0.000 abstract 1
- XLXSAKCOAKORKW-AQJXLSMYSA-N gonadorelin Chemical compound C([C@@H](C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N1[C@@H](CCC1)C(=O)NCC(N)=O)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@H]1NC(=O)CC1)C1=CC=C(O)C=C1 XLXSAKCOAKORKW-AQJXLSMYSA-N 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 108090000765 processed proteins & peptides Proteins 0.000 abstract 1
- 108020003175 receptors Proteins 0.000 abstract 1
- 230000008685 targeting Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/04—Linear peptides containing only normal peptide links
- C07K7/23—Luteinising hormone-releasing hormone [LHRH]; Related peptides
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Biophysics (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Epidemiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Genetics & Genomics (AREA)
- Endocrinology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Saccharide Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
La presente invencion se encuentra en el campo de la química de dirigir derivados de antraciclina anticancerosos, Más en particular, se relaciona con la doxorrubicina (DOX) o con sus derivados modificados de daunosamina (DM-DOX) ligados covalentemente a análogos de hormonas de péptidos, tales como LR-HR, bombesina y somatostatina. Estos conjugados covalentes se dirigen a varios tumores portadores de receptores para los análogos de hormonas de péptidos. Los compuestos de esta invencion están representados por la formula general: Q14-O-R-P, en la cual Q tiene la formula general (II), donde: Q14 significa una parte Q con una cadena lateral en la posicion 14; R- es H o -C(O)- (CH2)n-C(O)-y n = 0-7; R' es NH2 o un compuesto heterocíclico de 5 o 6 miembros, saturado o parcialmente saturado, aromático, que tiene por lo menos un nitrogeno de cadena cerrada y, opcionalmente, que tiene una parte de butadieno ligada a átomos de carbono adyacentes de dicha cadena cerrada para formar un sistema bicíclico; P es H o una parte de péptido, convenientemente un análogo de LHRH, somatostatina o bombesina. Sin embargo, cuando R y P son H, entonces R' debe ser distinta de NH2. Se ha descubierto una nueva reaccion sintética en el curso de este trabajo para formar partes heterocíclicas parcialmente saturadas a partir de aminas vicinales y disyuntivas, es decir alfa, beta- o alfa, y-hidroxi primarias. Q1 es DOX; Q2 es 3'-deamino-3'-(pirrolidin-1"-il)-doxorrubicina (AN 181); Q3 es 3'-deamino-3'-(isoindolin-1"-il)-doxorrubicina (AN 184); Q4 es 3'-deamino-3'-(32-pirrolin-1"-il)-doxorrubicina (AN 185): Q5 es 3'-deamino-3'-(3"-pirrolidon-1"-il)-doxorrubicina (AN 191); Q6 es 3'-deamino-3'(2"-pirrolin-1"-il)-doxorrubicina (AN 201); Q7 es 3'-deamino-3'-(3"-piperidon-1"-il)-doxorrubicina (AN 195); Q8 es 3'-deamino-3'-(1"-3"-tetrahidropiridin-1"-il)-doxo rrubicina (AN 205). Q114gL es AN 152; Q614gL es AN 207; Q114gS es AN 162; Q614gS es AN 238; Q114gB es AN 160; Q614gB es AN 215.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/562,652 US5843903A (en) | 1995-11-27 | 1995-11-27 | Targeted cytotoxic anthracycline analogs |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MX9804119A true MX9804119A (es) | 1998-09-30 |
Family
ID=24247176
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MX9804119A MX9804119A (es) | 1995-11-27 | 1998-05-25 | Analogos de antraciclina citotoxica dirigidos. |
Country Status (27)
| Country | Link |
|---|---|
| US (2) | US5843903A (es) |
| EP (2) | EP1384710B1 (es) |
| JP (2) | JP3987575B2 (es) |
| KR (2) | KR100445754B1 (es) |
| CN (2) | CN1166597C (es) |
| AT (2) | ATE401305T1 (es) |
| AU (1) | AU709539B2 (es) |
| BR (1) | BR9611647B1 (es) |
| CA (2) | CA2471775C (es) |
| CZ (1) | CZ297297B6 (es) |
| DE (2) | DE69630233T2 (es) |
| DK (2) | DK0863917T3 (es) |
| EA (1) | EA001372B1 (es) |
| ES (2) | ES2310222T3 (es) |
| HK (1) | HK1052920B (es) |
| HU (1) | HU229870B1 (es) |
| IL (3) | IL134685A (es) |
| IS (2) | IS2178B (es) |
| MX (1) | MX9804119A (es) |
| NO (2) | NO324035B1 (es) |
| NZ (1) | NZ322054A (es) |
| PL (3) | PL187230B1 (es) |
| PT (2) | PT863917E (es) |
| SK (2) | SK284392B6 (es) |
| UA (1) | UA67722C2 (es) |
| WO (1) | WO1997019954A1 (es) |
| ZA (1) | ZA969709B (es) |
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|---|---|---|---|---|
| US6576239B1 (en) | 1996-09-10 | 2003-06-10 | The Burnham Institute | Angiogenic homing molecules and conjugates derived therefrom |
| US6180084B1 (en) | 1998-08-25 | 2001-01-30 | The Burnham Institute | NGR receptor and methods of identifying tumor homing molecules that home to angiogenic vasculature using same |
| GB9814527D0 (en) | 1998-07-03 | 1998-09-02 | Cyclacel Ltd | Delivery system |
| JP2002530059A (ja) | 1998-11-13 | 2002-09-17 | サイクラセル・リミテッド | 輸送ベクター |
| FR2786397B1 (fr) * | 1998-11-30 | 2003-01-10 | Synt Em | Vecteurs peptidiques de substances a travers la barriere hematoencephalique pour etre utilises dans le diagnostic ou la therapie d'une affection du snc |
| FR2786398B1 (fr) * | 1998-11-30 | 2002-12-27 | Synt Em | Composition pharmaceutique anti-cancereuse et anti-chimioresistance comprenant un agent anticancereux et au moins un peptide |
| US6858598B1 (en) | 1998-12-23 | 2005-02-22 | G. D. Searle & Co. | Method of using a matrix metalloproteinase inhibitor and one or more antineoplastic agents as a combination therapy in the treatment of neoplasia |
| US6833373B1 (en) | 1998-12-23 | 2004-12-21 | G.D. Searle & Co. | Method of using an integrin antagonist and one or more antineoplastic agents as a combination therapy in the treatment of neoplasia |
| US6528481B1 (en) | 1999-02-16 | 2003-03-04 | The Burnam Institute | NG2/HM proteoglycan-binding peptides that home to angiogenic vasculature and related methods |
| US6380161B1 (en) | 1999-06-21 | 2002-04-30 | Inkine Pharmaceutical Company, Inc. | Compositions for treating chemotherapy-resistant tumor cells and targeted chemotherapy compositions |
| WO2001036007A2 (en) * | 1999-11-12 | 2001-05-25 | Angiotech Pharmaceuticals, Inc. | Compositions of a combination of radioactive therapy and cell-cycle inhibitors |
| CA2395660A1 (en) | 1999-12-29 | 2001-07-12 | Immunogen, Inc. | Cytotoxic agents comprising modified doxorubicins and daunorubicins and their therapeutic use |
| AU4267700A (en) * | 2000-01-13 | 2001-07-19 | Academia Sinica | Application of somatostatin analogs to specific delivery of anti-tumor drugs into tumor cells |
| EP1301540B1 (en) * | 2000-04-26 | 2004-07-28 | BioSynthema Inc. | Rgd (arg-gly-asp) coupled to neuropeptides |
| US7420030B2 (en) | 2000-09-08 | 2008-09-02 | The Board Of Regents Of The University Of Texas System | Aminopeptidase A (APA) targeting peptides for the treatment of cancer |
| US7452964B2 (en) | 2001-09-07 | 2008-11-18 | Board Of Regents, The University Of Texas System | Compositions and methods of use of targeting peptides against placenta and adipose tissues |
| US20040170955A1 (en) | 2000-09-08 | 2004-09-02 | Wadih Arap | Human and mouse targeting peptides identified by phage display |
| KR100420007B1 (ko) * | 2001-04-25 | 2004-03-02 | 노영쇠 | 안트라사이클린 유도체 및 이를 포함하는 항암제 |
| US7326685B2 (en) * | 2001-09-21 | 2008-02-05 | The Administrators Of The Tulane Educational Fund | Diagnostic or therapeutic somatostatin or bombesin analog conjugates and uses thereof |
| AU2003224644A1 (en) * | 2002-02-27 | 2003-09-09 | The Government Of The United States Of America, Represented By The Secretary, Department Of Healtan | Conjugates of ligand, linker and cytotoxic agent and related compositions and methods of use |
| US7771727B2 (en) | 2002-03-01 | 2010-08-10 | The Administrators Of The Tulane Educational Fund | Conjugates of therapeutic or cytotoxic agents and biologically active peptides |
| US7544767B2 (en) | 2002-04-05 | 2009-06-09 | Burnham Institute For Medical Research | HMGN2 peptides and related molecules that selectively home to tumor blood vessels and tumor cells |
| JP5000848B2 (ja) * | 2002-05-21 | 2012-08-15 | 第一三共株式会社 | グレリン含有医薬組成物 |
| EP1509256B1 (en) | 2002-05-24 | 2009-07-22 | Angiotech International Ag | Compositions and methods for coating medical implants |
| US8313760B2 (en) | 2002-05-24 | 2012-11-20 | Angiotech International Ag | Compositions and methods for coating medical implants |
| BR0314743A (pt) | 2002-09-26 | 2005-07-26 | Angiotech Int Ag | Envoltórios perivasculares |
| JP2006516548A (ja) | 2002-12-30 | 2006-07-06 | アンジオテック インターナショナル アクツィエン ゲゼルシャフト | 迅速ゲル化ポリマー組成物からの薬物送達法 |
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| US7097993B2 (en) | 2003-06-25 | 2006-08-29 | Wisconsin Alumni Research Foundation | Method for identifying an agent that modulates type 1 phosphatidylinositol phosphate kinase isoform β661 activity |
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| BR112013013127B1 (pt) | 2010-12-02 | 2021-06-22 | Nerviano Medical Sciences S.R.L. | Processo para a preparação de derivados de morfolinil antraciclina, compostos derivados de morfolinil antraciclina e composição farmacêutica compreendendo estes compostos |
| CN105198966B (zh) * | 2014-06-26 | 2019-06-21 | 中国人民解放军军事医学科学院毒物药物研究所 | GnRH类似物-细胞毒分子缀合物、其制备方法及用途 |
| KR102062025B1 (ko) | 2014-06-30 | 2020-01-03 | 타베다 세라퓨틱스, 인코포레이티드 | 표적화된 콘주게이트 및 입자 및 그것의 제형 |
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| AU2016343817B2 (en) | 2015-10-28 | 2021-05-27 | Tva (Abc), Llc | SSTR-targeted conjugates and particles and formulations thereof |
| US10450340B2 (en) | 2017-02-16 | 2019-10-22 | Monopar Therapeutics Inc. | 3′-deamino-3′-(2″-pyrroline-1″-yl)-5-imino-13-deoxyanthracyclines and methods of preparation |
| CN120081907A (zh) * | 2018-11-13 | 2025-06-03 | 省卫生服务机构 | 用于胃泌素释放肽受体（grpr）的体内成像和治疗grpr相关病症的放射性标记蛙皮素衍生化合物 |
| JP2025510161A (ja) | 2022-03-25 | 2025-04-14 | プロビンシャル・ヘルス・サービシーズ・オーソリティ | ガストリン放出ペプチド受容体（ｇｒｐｒ）のインビボイメージング及びｇｒｐｒ関連障害の治療のための放射性標識化合物 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3725350A (en) * | 1972-04-26 | 1973-04-03 | Commercial Soluents Corp | Polymeric substances comprising the reaction product of melamine, aldehyde and oxazolidines |
| US4299822A (en) * | 1980-06-09 | 1981-11-10 | Sidney Farber Cancer Institute, Inc. | N-Trifluoroacetyladriamycin-14-O-hemiglutarate and -hemiadipate and therapeutic compositions containing same |
| US4464529A (en) * | 1982-07-20 | 1984-08-07 | Sri International | Analogues of morpholinyl daunorubicin and morpholinyl doxorubicin |
| IL89220A (en) * | 1988-02-11 | 1994-02-27 | Bristol Myers Squibb Co | Anthracycline immunoconjugates, their production and pharmaceutical compositions containing them |
| US5217955A (en) * | 1989-09-15 | 1993-06-08 | Biomeasure, Inc. | Treatment of cancer with peptide analog of bombesin, grp, litorin or neuromedin |
| US5304687A (en) * | 1989-12-19 | 1994-04-19 | Farmitalia Carlo Erba S.R.L. | Morpholinyl derivatives of doxorubicin and process for their preparation |
| ES2094136T3 (es) * | 1989-12-19 | 1997-01-16 | Pharmacia Spa | Intermediarios quirales de 1,5-diyodo-2-metoxi o benciloxi. |
| DE69112684T2 (de) * | 1990-04-06 | 1996-02-01 | Univ Tulane | LHRH-Analoge. |
| EP0450480B1 (en) * | 1990-04-06 | 1995-06-21 | The Administrators of The Tulane Educational Fund | Somatostatin Analogues |
| JP3169425B2 (ja) * | 1992-03-27 | 2001-05-28 | 三共株式会社 | アジドペンタンサイクリトール |
| US6214345B1 (en) * | 1993-05-14 | 2001-04-10 | Bristol-Myers Squibb Co. | Lysosomal enzyme-cleavable antitumor drug conjugates |
-
1995
- 1995-11-27 US US08/562,652 patent/US5843903A/en not_active Expired - Lifetime
-
1996
- 1996-11-14 DK DK96938216T patent/DK0863917T3/da active
- 1996-11-14 HU HU9903771A patent/HU229870B1/hu unknown
- 1996-11-14 BR BRPI9611647-1A patent/BR9611647B1/pt not_active IP Right Cessation
- 1996-11-14 EP EP03010988A patent/EP1384710B1/en not_active Expired - Lifetime
- 1996-11-14 DE DE69630233T patent/DE69630233T2/de not_active Expired - Lifetime
- 1996-11-14 JP JP52012397A patent/JP3987575B2/ja not_active Expired - Lifetime
- 1996-11-14 NZ NZ322054A patent/NZ322054A/en not_active IP Right Cessation
- 1996-11-14 EA EA199800492A patent/EA001372B1/ru not_active IP Right Cessation
- 1996-11-14 CZ CZ0135798A patent/CZ297297B6/cs not_active IP Right Cessation
- 1996-11-14 AT AT03010988T patent/ATE401305T1/de active
- 1996-11-14 KR KR10-1998-0703948A patent/KR100445754B1/ko not_active Expired - Lifetime
- 1996-11-14 ES ES03010988T patent/ES2310222T3/es not_active Expired - Lifetime
- 1996-11-14 SK SK628-98A patent/SK284392B6/sk unknown
- 1996-11-14 KR KR10-2004-7004548A patent/KR100467899B1/ko not_active Expired - Lifetime
- 1996-11-14 CN CNB021439192A patent/CN1166597C/zh not_active Expired - Lifetime
- 1996-11-14 PL PL96326865A patent/PL187230B1/pl unknown
- 1996-11-14 WO PCT/EP1996/005029 patent/WO1997019954A1/en not_active Ceased
- 1996-11-14 CA CA002471775A patent/CA2471775C/en not_active Expired - Lifetime
- 1996-11-14 CA CA002238574A patent/CA2238574C/en not_active Expired - Lifetime
- 1996-11-14 SK SK341-2004A patent/SK284672B6/sk not_active IP Right Cessation
- 1996-11-14 PL PL96358646A patent/PL188786B1/pl unknown
- 1996-11-14 EP EP96938216A patent/EP0863917B1/en not_active Expired - Lifetime
- 1996-11-14 PT PT96938216T patent/PT863917E/pt unknown
- 1996-11-14 PL PL358737A patent/PL191781B1/pl unknown
- 1996-11-14 ES ES96938216T patent/ES2205067T3/es not_active Expired - Lifetime
- 1996-11-14 AT AT96938216T patent/ATE251179T1/de active
- 1996-11-14 UA UA98063318A patent/UA67722C2/uk unknown
- 1996-11-14 PT PT03010988T patent/PT1384710E/pt unknown
- 1996-11-14 CN CNB961986050A patent/CN1137136C/zh not_active Expired - Lifetime
- 1996-11-14 DK DK03010988T patent/DK1384710T3/da active
- 1996-11-14 DE DE69637604T patent/DE69637604D1/de not_active Expired - Lifetime
- 1996-11-14 AU AU75722/96A patent/AU709539B2/en not_active Expired
- 1996-11-20 ZA ZA9609709A patent/ZA969709B/xx unknown
- 1996-11-26 IL IL13468596A patent/IL134685A/en not_active IP Right Cessation
- 1996-11-26 IL IL11969196A patent/IL119691A/en not_active IP Right Cessation
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1998
- 1998-05-05 IS IS4734A patent/IS2178B/is unknown
- 1998-05-15 NO NO19982252A patent/NO324035B1/no not_active IP Right Cessation
- 1998-05-25 MX MX9804119A patent/MX9804119A/es unknown
- 1998-07-15 US US09/116,125 patent/US6184374B1/en not_active Expired - Lifetime
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2000
- 2000-02-23 IL IL13468500A patent/IL134685A0/xx unknown
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2003
- 2003-07-09 HK HK03104934.8A patent/HK1052920B/zh not_active IP Right Cessation
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2005
- 2005-03-01 NO NO20051111A patent/NO20051111L/no not_active Application Discontinuation
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2006
- 2006-11-09 IS IS8567A patent/IS2634B/is unknown
- 2006-11-15 JP JP2006309698A patent/JP4778405B2/ja not_active Expired - Lifetime
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