AU739028B2 - Hydrolyzable prodrugs for delivery of anticancer drugs to metastatic cells - Google Patents
Hydrolyzable prodrugs for delivery of anticancer drugs to metastatic cells Download PDFInfo
- Publication number
- AU739028B2 AU739028B2 AU45995/97A AU4599597A AU739028B2 AU 739028 B2 AU739028 B2 AU 739028B2 AU 45995/97 A AU45995/97 A AU 45995/97A AU 4599597 A AU4599597 A AU 4599597A AU 739028 B2 AU739028 B2 AU 739028B2
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- Australia
- Prior art keywords
- peptide
- hydrolyzable
- amino
- reagent
- lys
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 239000006193 liquid solution Substances 0.000 description 1
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- GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium hydroxide monohydrate Substances [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 description 1
- 229940040692 lithium hydroxide monohydrate Drugs 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
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- 238000002844 melting Methods 0.000 description 1
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- 208000021039 metastatic melanoma Diseases 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 238000011227 neoadjuvant chemotherapy Methods 0.000 description 1
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- 229910052757 nitrogen Inorganic materials 0.000 description 1
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- 238000011275 oncology therapy Methods 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 description 1
- 230000004962 physiological condition Effects 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000004302 potassium sorbate Substances 0.000 description 1
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- 230000004044 response Effects 0.000 description 1
- 201000006845 reticulosarcoma Diseases 0.000 description 1
- 208000029922 reticulum cell sarcoma Diseases 0.000 description 1
- 230000011664 signaling Effects 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- KEAYESYHFKHZAL-OUBTZVSYSA-N sodium-24 Chemical compound [24Na] KEAYESYHFKHZAL-OUBTZVSYSA-N 0.000 description 1
- XZPVPNZTYPUODG-UHFFFAOYSA-M sodium;chloride;dihydrate Chemical compound O.O.[Na+].[Cl-] XZPVPNZTYPUODG-UHFFFAOYSA-M 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
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- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 230000004614 tumor growth Effects 0.000 description 1
- 125000002987 valine group Chemical group [H]N([H])C([H])(C(*)=O)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000002348 vinylic group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- C07K14/435—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- C07K14/78—Connective tissue peptides, e.g. collagen, elastin, laminin, fibronectin, vitronectin or cold insoluble globulin [CIG]
-
- 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
- A61K47/65—Peptidic linkers, binders or spacers, e.g. peptidic enzyme-labile linkers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06008—Dipeptides with the first amino acid being neutral
- C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
- C07K5/06034—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 2 to 4 carbon atoms
- C07K5/06052—Val-amino acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06008—Dipeptides with the first amino acid being neutral
- C07K5/06078—Dipeptides with the first amino acid being neutral and aromatic or cycloaliphatic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/08—Tripeptides
- C07K5/0815—Tripeptides with the first amino acid being basic
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Medicinal Chemistry (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Toxicology (AREA)
- Zoology (AREA)
- Gastroenterology & Hepatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US4433496P | 1996-09-27 | 1996-09-27 | |
| US60/044334 | 1996-09-27 | ||
| PCT/US1997/017410 WO1998013059A1 (fr) | 1996-09-27 | 1997-09-25 | Promedicaments hydrolysables pour la liberation de medicaments anticancereux dans des cellules metastatiques |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU4599597A AU4599597A (en) | 1998-04-17 |
| AU739028B2 true AU739028B2 (en) | 2001-10-04 |
Family
ID=21931799
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU45995/97A Ceased AU739028B2 (en) | 1996-09-27 | 1997-09-25 | Hydrolyzable prodrugs for delivery of anticancer drugs to metastatic cells |
Country Status (4)
| Country | Link |
|---|---|
| EP (1) | EP0961619A4 (fr) |
| AU (1) | AU739028B2 (fr) |
| CA (1) | CA2264227A1 (fr) |
| WO (1) | WO1998013059A1 (fr) |
Families Citing this family (135)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19636889A1 (de) | 1996-09-11 | 1998-03-12 | Felix Dr Kratz | Antineoplastisch wirkende Transferrin- und Albuminkonjugate zytostatischer Verbindungen aus der Gruppe der Anthrazykline, Alkylantien, Antimetabolite und Cisplatin-Analoga und diese enthaltende Arzneimittel |
| WO1999025729A1 (fr) * | 1997-11-18 | 1999-05-27 | Chugai Seiyaku Kabushiki Kaisha | Composes possedant une activite antitumorale |
| US6180095B1 (en) | 1997-12-17 | 2001-01-30 | Enzon, Inc. | Polymeric prodrugs of amino- and hydroxyl-containing bioactive agents |
| WO1999030727A1 (fr) | 1997-12-17 | 1999-06-24 | Enzon, Inc. | Prodrogues polymeriques d'agents bioactifs contenant amine ou hydroxy |
| US6624142B2 (en) | 1997-12-30 | 2003-09-23 | Enzon, Inc. | Trimethyl lock based tetrapartate prodrugs |
| US5965119A (en) | 1997-12-30 | 1999-10-12 | Enzon, Inc. | Trialkyl-lock-facilitated polymeric prodrugs of amino-containing bioactive agents |
| US6835807B1 (en) | 1998-05-22 | 2004-12-28 | Daiichi Pharmaceuticals Co., Ltd. | Drug complex and drug delivery system |
| GB9814527D0 (en) * | 1998-07-03 | 1998-09-02 | Cyclacel Ltd | Delivery system |
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| EP1958961A3 (fr) | 1998-11-13 | 2008-09-03 | Cyclacel Limited | Vecteurs de transport |
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| CA2383798A1 (fr) * | 1999-09-07 | 2001-03-15 | Conjuchem Inc. | Diffusion pulmonaire permettant la bioconjugaison |
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| US4703107A (en) * | 1983-05-16 | 1987-10-27 | Centre National De La Recherche Scientifique (Cnrs) | Water-soluble acylated derivatives of peptides or amino acids, their preparation and their use |
| EP0624377A2 (fr) * | 1993-05-14 | 1994-11-17 | Bristol-Myers Squibb Company | Conjugués antitumoraux divables pour enzyme lysosomiales |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2001505194A (ja) * | 1996-11-05 | 2001-04-17 | ブリストル―マイヤーズ・スクイブ・カンパニー | 分枝ペプチド・リンカー |
-
1997
- 1997-09-25 WO PCT/US1997/017410 patent/WO1998013059A1/fr not_active Application Discontinuation
- 1997-09-25 AU AU45995/97A patent/AU739028B2/en not_active Ceased
- 1997-09-25 CA CA002264227A patent/CA2264227A1/fr not_active Abandoned
- 1997-09-25 EP EP97944519A patent/EP0961619A4/fr not_active Withdrawn
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4703107A (en) * | 1983-05-16 | 1987-10-27 | Centre National De La Recherche Scientifique (Cnrs) | Water-soluble acylated derivatives of peptides or amino acids, their preparation and their use |
| EP0624377A2 (fr) * | 1993-05-14 | 1994-11-17 | Bristol-Myers Squibb Company | Conjugués antitumoraux divables pour enzyme lysosomiales |
Also Published As
| Publication number | Publication date |
|---|---|
| WO1998013059A1 (fr) | 1998-04-02 |
| AU4599597A (en) | 1998-04-17 |
| EP0961619A4 (fr) | 2001-09-26 |
| CA2264227A1 (fr) | 1998-04-02 |
| EP0961619A1 (fr) | 1999-12-08 |
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