CA2408501C - Melphalan derivatives and their use as cancer chemotherapeutic drugs - Google Patents
Melphalan derivatives and their use as cancer chemotherapeutic drugs Download PDFInfo
- Publication number
- CA2408501C CA2408501C CA2408501A CA2408501A CA2408501C CA 2408501 C CA2408501 C CA 2408501C CA 2408501 A CA2408501 A CA 2408501A CA 2408501 A CA2408501 A CA 2408501A CA 2408501 C CA2408501 C CA 2408501C
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- CA
- Canada
- Prior art keywords
- melphalan
- mmol
- ethyl ester
- chz
- cancer
- 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.)
- Expired - Lifetime
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- 201000011510 cancer Diseases 0.000 title claims description 18
- SGDBTWWWUNNDEQ-LBPRGKRZSA-N melphalan Chemical class OC(=O)[C@@H](N)CC1=CC=C(N(CCCl)CCCl)C=C1 SGDBTWWWUNNDEQ-LBPRGKRZSA-N 0.000 title abstract description 60
- 206010028980 Neoplasm Diseases 0.000 title description 64
- 239000002246 antineoplastic agent Substances 0.000 title description 6
- 229940044683 chemotherapy drug Drugs 0.000 title description 4
- 108090000765 processed proteins & peptides Proteins 0.000 claims abstract description 47
- 238000011282 treatment Methods 0.000 claims abstract description 20
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 10
- 239000003814 drug Substances 0.000 claims description 33
- -1 aromatic amino acid Chemical class 0.000 claims description 20
- 150000001875 compounds Chemical class 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 13
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- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 206010033128 Ovarian cancer Diseases 0.000 claims description 7
- 206010035226 Plasma cell myeloma Diseases 0.000 claims description 6
- 125000004122 cyclic group Chemical group 0.000 claims description 6
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- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
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- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 4
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 64
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- 239000000243 solution Substances 0.000 description 34
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Classifications
-
- 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
- C07K5/06191—Dipeptides containing heteroatoms different from O, S, or N
-
- 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
- A61P35/02—Antineoplastic agents specific for leukemia
-
- 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
- C07K5/0827—Tripeptides containing heteroatoms different from O, S, or N
-
- 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)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Biochemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Molecular Biology (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biophysics (AREA)
- Genetics & Genomics (AREA)
- Hematology (AREA)
- Oncology (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US21122700P | 2000-06-13 | 2000-06-13 | |
| SE0002202-0 | 2000-06-13 | ||
| SE0002202A SE0002202D0 (sv) | 2000-06-13 | 2000-06-13 | New peptides |
| US60/211,227 | 2000-06-13 | ||
| PCT/SE2001/001318 WO2001096367A1 (en) | 2000-06-13 | 2001-06-11 | Melphalan derivatives and their use as cancer chemotherapeutic drugs |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2408501A1 CA2408501A1 (en) | 2001-12-20 |
| CA2408501C true CA2408501C (en) | 2011-01-18 |
Family
ID=20280067
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2408501A Expired - Lifetime CA2408501C (en) | 2000-06-13 | 2001-06-11 | Melphalan derivatives and their use as cancer chemotherapeutic drugs |
Country Status (10)
| Country | Link |
|---|---|
| EP (1) | EP1290011B1 (enExample) |
| JP (1) | JP4798930B2 (enExample) |
| AT (1) | ATE458746T1 (enExample) |
| AU (1) | AU2001264515A1 (enExample) |
| CA (1) | CA2408501C (enExample) |
| DK (1) | DK1290011T3 (enExample) |
| ES (1) | ES2341702T3 (enExample) |
| PT (1) | PT1290011E (enExample) |
| SE (1) | SE0002202D0 (enExample) |
| WO (1) | WO2001096367A1 (enExample) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1374907A3 (en) * | 2002-06-24 | 2004-01-07 | Ghanem Elias c/o Institut Jules Bordet Ghanem | Drug transport and delivery system |
| DE10239832A1 (de) * | 2002-08-29 | 2004-03-18 | Lipal Biochemicals AG c/o University of Zurich | Sarcolysyl-Derivate und Verfahren zu deren Herstellung |
| WO2011011865A1 (en) * | 2009-07-29 | 2011-02-03 | 3R Valo, S.E.C. | Anticancer agents based on amino acid derivatives |
| WO2011078782A1 (en) * | 2009-12-22 | 2011-06-30 | Oncopeptides Ab | A composition comprising of melphalan derivatives and gemcitabine or etoposide useful in the treatment of cancer |
| HUE037863T2 (hu) | 2011-04-28 | 2018-09-28 | Oncopeptides Ab | Citotoxikus dipeptidek liofilizált készítménye |
| PT3228319T (pt) * | 2011-04-28 | 2020-08-27 | Oncopeptides Ab | Preparação liofilizada de dipéptidos citotóxicos |
| RS60068B1 (sr) * | 2012-10-26 | 2020-05-29 | Oncopeptides Ab | Liofilisani preparati melfalan flufenamida |
| DK2928463T3 (da) * | 2012-10-26 | 2020-02-24 | Oncopeptides Ab | Lyofiliserede præparater af melphalan-flufenamid |
| GB201507903D0 (en) | 2015-05-08 | 2015-06-24 | Oncopeptides Ab | Process for preparation of nitrogen mustard derivatives |
| GB201521217D0 (en) | 2015-12-01 | 2016-01-13 | Oncopeptides Ab | Dosage regimens |
| CN108864251B (zh) * | 2018-06-30 | 2022-06-14 | 大连理工大学 | 一类氨肽酶n激活的药物前体化合物及其制备方法和应用 |
| HUE061801T2 (hu) | 2018-10-18 | 2023-08-28 | Oncopeptides Ab | Deutérium-tartalmú vegyületek |
| US12396975B2 (en) | 2019-04-03 | 2025-08-26 | Oncopeptides Ab | Treatment of al amyloidosis with melflufen |
| GB201905477D0 (en) * | 2019-04-17 | 2019-05-29 | Oncopeptides Ab | Novel formulations |
| WO2021053185A1 (en) | 2019-09-20 | 2021-03-25 | Oncopeptides Ab | Melflufen formulations and their use in the treatment or prophylaxis of osteosarcoma |
| WO2022167087A1 (en) * | 2021-02-05 | 2022-08-11 | Oncopeptides Ab | Peptidase enhanced cytotoxic dipeptides |
| EP4083052A1 (en) | 2021-04-29 | 2022-11-02 | BKmdcl AB | Peptide conjugates of melphalan for the treatment of cancer |
| EP4347615B1 (en) | 2021-06-01 | 2025-05-21 | Synthon B.V. | Process for making melflufen or a salt thereof |
| GB202109896D0 (en) | 2021-07-08 | 2021-08-25 | Oncopeptides Ab | Novel treatments |
| GB202109894D0 (en) | 2021-07-08 | 2021-08-25 | Oncopeptides Ab | Novel treatments |
| GB202109895D0 (en) | 2021-07-08 | 2021-08-25 | Oncopeptides Ab | Novel treatments |
| EP4366721A1 (en) | 2021-07-08 | 2024-05-15 | Oncopeptides Innovation AB | Melflufen for use in the treatment of multiple myeloma |
| GB202204171D0 (en) | 2022-03-24 | 2022-05-11 | Oncopeptides Ab | Novel formulations |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB750155A (en) | 1953-03-17 | 1956-06-13 | Nat Res Dev | Substituted alanines |
-
2000
- 2000-06-13 SE SE0002202A patent/SE0002202D0/xx unknown
-
2001
- 2001-06-11 CA CA2408501A patent/CA2408501C/en not_active Expired - Lifetime
- 2001-06-11 EP EP01938945A patent/EP1290011B1/en not_active Expired - Lifetime
- 2001-06-11 AT AT01938945T patent/ATE458746T1/de not_active IP Right Cessation
- 2001-06-11 PT PT01938945T patent/PT1290011E/pt unknown
- 2001-06-11 JP JP2002510508A patent/JP4798930B2/ja not_active Expired - Lifetime
- 2001-06-11 AU AU2001264515A patent/AU2001264515A1/en not_active Abandoned
- 2001-06-11 WO PCT/SE2001/001318 patent/WO2001096367A1/en not_active Ceased
- 2001-06-11 DK DK01938945.1T patent/DK1290011T3/da active
- 2001-06-11 ES ES01938945T patent/ES2341702T3/es not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| AU2001264515A1 (en) | 2001-12-24 |
| CA2408501A1 (en) | 2001-12-20 |
| JP4798930B2 (ja) | 2011-10-19 |
| DK1290011T3 (da) | 2010-06-07 |
| EP1290011B1 (en) | 2010-02-24 |
| SE0002202D0 (sv) | 2000-06-13 |
| JP2004503564A (ja) | 2004-02-05 |
| WO2001096367A1 (en) | 2001-12-20 |
| EP1290011A1 (en) | 2003-03-12 |
| ES2341702T3 (es) | 2010-06-25 |
| PT1290011E (pt) | 2010-05-11 |
| ATE458746T1 (de) | 2010-03-15 |
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| Date | Code | Title | Description |
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| EEER | Examination request | ||
| MKEX | Expiry |
Effective date: 20210611 |