CA2562572A1 - Camptothecin derivatives conjugated in position 20 with integrin antagonists - Google Patents
Camptothecin derivatives conjugated in position 20 with integrin antagonists Download PDFInfo
- Publication number
- CA2562572A1 CA2562572A1 CA002562572A CA2562572A CA2562572A1 CA 2562572 A1 CA2562572 A1 CA 2562572A1 CA 002562572 A CA002562572 A CA 002562572A CA 2562572 A CA2562572 A CA 2562572A CA 2562572 A1 CA2562572 A1 CA 2562572A1
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- branched
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- alkyl
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- VSJKWCGYPAHWDS-FQEVSTJZSA-N camptothecin Chemical class C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-FQEVSTJZSA-N 0.000 title claims abstract description 16
- 102000006495 integrins Human genes 0.000 title abstract description 13
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- 229940127093 camptothecin Drugs 0.000 claims abstract description 7
- VSJKWCGYPAHWDS-UHFFFAOYSA-N dl-camptothecin Natural products C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)C5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-UHFFFAOYSA-N 0.000 claims abstract description 7
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- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
- 229910017849 NH2—NH2 Inorganic materials 0.000 description 1
- 108700019961 Neoplasm Genes Proteins 0.000 description 1
- 102000048850 Neoplasm Genes Human genes 0.000 description 1
- 206010061535 Ovarian neoplasm Diseases 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- 206010039491 Sarcoma Diseases 0.000 description 1
- 239000000365 Topoisomerase I Inhibitor Substances 0.000 description 1
- OBTCMSPFOITUIJ-FSPLSTOPSA-N Val-Asp Chemical compound CC(C)[C@H](N)C(=O)N[C@H](C(O)=O)CC(O)=O OBTCMSPFOITUIJ-FSPLSTOPSA-N 0.000 description 1
- 108010031318 Vitronectin Proteins 0.000 description 1
- 102100035140 Vitronectin Human genes 0.000 description 1
- 108010048673 Vitronectin Receptors Proteins 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 1
- 230000002491 angiogenic effect Effects 0.000 description 1
- 230000002001 anti-metastasis Effects 0.000 description 1
- 239000003096 antiparasitic agent Substances 0.000 description 1
- 235000003704 aspartic acid Nutrition 0.000 description 1
- JHVLLYQQQYIWKX-UHFFFAOYSA-N benzyl 2-bromoacetate Chemical compound BrCC(=O)OCC1=CC=CC=C1 JHVLLYQQQYIWKX-UHFFFAOYSA-N 0.000 description 1
- HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 1
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 230000000973 chemotherapeutic effect Effects 0.000 description 1
- 238000013270 controlled release Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 231100000433 cytotoxic Toxicity 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- WBKFWQBXFREOFH-UHFFFAOYSA-N dichloromethane;ethyl acetate Chemical compound ClCCl.CCOC(C)=O WBKFWQBXFREOFH-UHFFFAOYSA-N 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- HCUYBXPSSCRKRF-UHFFFAOYSA-N diphosgene Chemical compound ClC(=O)OC(Cl)(Cl)Cl HCUYBXPSSCRKRF-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- XSVCYDUEICANRJ-UHFFFAOYSA-K dysprosium(3+);trifluoromethanesulfonate Chemical compound [Dy+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F XSVCYDUEICANRJ-UHFFFAOYSA-K 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 210000003038 endothelium Anatomy 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 235000019439 ethyl acetate Nutrition 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000001415 gene therapy Methods 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 210000005260 human cell Anatomy 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
- 230000009871 nonspecific binding Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
- 125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000000861 pro-apoptotic effect Effects 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000009901 transfer hydrogenation reaction Methods 0.000 description 1
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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
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- 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
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Epidemiology (AREA)
- Molecular Biology (AREA)
- Oncology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Virology (AREA)
- Communicable Diseases (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ITRM2004A000241 | 2004-05-13 | ||
| IT000241A ITRM20040241A1 (it) | 2004-05-13 | 2004-05-13 | Camptotecine coniugate in posizione 20 con antagonisti delle integrine. |
| PCT/IT2005/000261 WO2005110487A2 (en) | 2004-05-13 | 2005-05-04 | Camptothecin derivatives conjugated in position 20 with integrin antagonists |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2562572A1 true CA2562572A1 (en) | 2005-11-24 |
Family
ID=35124307
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002562572A Abandoned CA2562572A1 (en) | 2004-05-13 | 2005-05-04 | Camptothecin derivatives conjugated in position 20 with integrin antagonists |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US20070232639A1 (enExample) |
| EP (1) | EP1747019A2 (enExample) |
| JP (1) | JP2007537244A (enExample) |
| CN (1) | CN101010103A (enExample) |
| AR (1) | AR049275A1 (enExample) |
| AU (1) | AU2005243834A1 (enExample) |
| BR (1) | BRPI0511037A (enExample) |
| CA (1) | CA2562572A1 (enExample) |
| IT (1) | ITRM20040241A1 (enExample) |
| MX (1) | MXPA06012886A (enExample) |
| TW (1) | TW200538125A (enExample) |
| WO (1) | WO2005110487A2 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2606911A1 (en) * | 2007-02-16 | 2013-06-26 | KTB Tumorforschungsgesellschaft mbH | Receptor And Antigen Targeted Prodrug |
| MX2014008373A (es) * | 2012-01-27 | 2014-09-26 | Hoffmann La Roche | Conjugados antagonistas de integrina para suministro dirigido a celulas que expresan alfa-v-beta-3. |
| CN105399757A (zh) * | 2015-12-29 | 2016-03-16 | 遵义医学院 | 酸敏感型喜树碱-20位去甲斑蝥酸酯衍生物及其抗肿瘤应用 |
| CN111068068A (zh) * | 2019-12-04 | 2020-04-28 | 云南民族大学 | 一种rgd多肽-喜树碱多肽药物偶联物及其应用 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19815812A1 (de) * | 1998-04-08 | 1999-10-14 | Bayer Ag | Modifizierte Cytostatika |
| ATE216998T1 (de) * | 1999-03-09 | 2002-05-15 | Sigma Tau Ind Farmaceuti | Camptothecin-derivate mit antitumor-wirkung |
| US6207832B1 (en) * | 1999-04-09 | 2001-03-27 | University Of Pittsburgh | Camptothecin analogs and methods of preparation thereof |
| HUP0203899A3 (en) * | 1999-09-08 | 2004-09-28 | Bayer Ag | Conjugates containing alphavbetha3 or alphavbetha5 integrin antagonist and cytostatic, process for their preparation and pharmaceutical compositions containing the same |
-
2004
- 2004-05-13 IT IT000241A patent/ITRM20040241A1/it unknown
-
2005
- 2005-05-04 BR BRPI0511037-8A patent/BRPI0511037A/pt not_active IP Right Cessation
- 2005-05-04 EP EP05743015A patent/EP1747019A2/en not_active Withdrawn
- 2005-05-04 TW TW094114403A patent/TW200538125A/zh unknown
- 2005-05-04 WO PCT/IT2005/000261 patent/WO2005110487A2/en not_active Ceased
- 2005-05-04 CN CNA2005800152323A patent/CN101010103A/zh active Pending
- 2005-05-04 CA CA002562572A patent/CA2562572A1/en not_active Abandoned
- 2005-05-04 JP JP2007512735A patent/JP2007537244A/ja not_active Withdrawn
- 2005-05-04 MX MXPA06012886A patent/MXPA06012886A/es not_active Application Discontinuation
- 2005-05-04 US US11/596,189 patent/US20070232639A1/en not_active Abandoned
- 2005-05-04 AU AU2005243834A patent/AU2005243834A1/en not_active Abandoned
- 2005-05-12 AR ARP050101933A patent/AR049275A1/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ITRM20040241A1 (it) | 2004-08-13 |
| US20070232639A1 (en) | 2007-10-04 |
| TW200538125A (en) | 2005-12-01 |
| EP1747019A2 (en) | 2007-01-31 |
| CN101010103A (zh) | 2007-08-01 |
| WO2005110487A3 (en) | 2007-02-15 |
| AU2005243834A1 (en) | 2005-11-24 |
| WO2005110487A2 (en) | 2005-11-24 |
| JP2007537244A (ja) | 2007-12-20 |
| AR049275A1 (es) | 2006-07-12 |
| BRPI0511037A (pt) | 2007-11-27 |
| MXPA06012886A (es) | 2007-02-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |