CA2501089A1 - 4-methylhexanoic kahalaide f compound - Google Patents

4-methylhexanoic kahalaide f compound Download PDF

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Publication number
CA2501089A1
CA2501089A1 CA002501089A CA2501089A CA2501089A1 CA 2501089 A1 CA2501089 A1 CA 2501089A1 CA 002501089 A CA002501089 A CA 002501089A CA 2501089 A CA2501089 A CA 2501089A CA 2501089 A1 CA2501089 A1 CA 2501089A1
Authority
CA
Canada
Prior art keywords
cancer
compound
pharmaceutically acceptable
affected
psoriasis
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.)
Granted
Application number
CA002501089A
Other languages
French (fr)
Other versions
CA2501089C (en
Inventor
Glynn Thomas Faircloth
Mariano Elices
Halina Sasak
Pablo Manuel Aviles Marin
Maria Del Carmen Cuevas Marchante
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Pharmamar SA
Original Assignee
Individual
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority claimed from PCT/GB2002/004735 external-priority patent/WO2003033012A1/en
Priority claimed from GBGB0304367.6A external-priority patent/GB0304367D0/en
Priority claimed from GB0314725A external-priority patent/GB0314725D0/en
Application filed by Individual filed Critical Individual
Publication of CA2501089A1 publication Critical patent/CA2501089A1/en
Application granted granted Critical
Publication of CA2501089C publication Critical patent/CA2501089C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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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
    • C07K7/08—Linear peptides containing only normal peptide links having 12 to 20 amino acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/06—Antipsoriatics
    • 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
    • A61P31/10—Antimycotics
    • 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
    • A61P35/00—Antineoplastic agents
    • 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
    • C07K14/46—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans from vertebrates
    • C07K14/47—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans from vertebrates from mammals
    • C07K14/4701—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans from vertebrates from mammals not used
    • C07K14/4748—Tumour specific antigens; Tumour rejection antigen precursors [TRAP], e.g. MAGE
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
    • C07K7/50—Cyclic peptides containing at least one abnormal peptide link
    • C07K7/54—Cyclic peptides containing at least one abnormal peptide link with at least one abnormal peptide link in the ring
    • C07K7/56—Cyclic peptides containing at least one abnormal peptide link with at least one abnormal peptide link in the ring the cyclisation not occurring through 2,4-diamino-butanoic acid
    • 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)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Animal Behavior & Ethology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Biophysics (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Molecular Biology (AREA)
  • Genetics & Genomics (AREA)
  • Biochemistry (AREA)
  • Oncology (AREA)
  • Communicable Diseases (AREA)
  • Engineering & Computer Science (AREA)
  • Dermatology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Virology (AREA)
  • Immunology (AREA)
  • Toxicology (AREA)
  • Zoology (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Peptides Or Proteins (AREA)

Abstract

The present invention is directed to new kahalalide antitumoral compounds, in particular to analogues of kahalalide F, useful as antitumoral, antiviral, antifungal agents and in the treatment of psoriasis.

Claims (13)

1. A compound of formula 1:
and pharmaceutically acceptable salts, prodrugs, tautomers, and solvates, thereof.
2. A compound having the formula 2:

and pharmaceutically acceptable salts, prodrugs, tautomers, and solvates, thereof.
3. A pharmaceutical composition comprising a compound as defined in claims 1 or 2 and a pharmaceutically acceptable carrier, vehicle or diluent.
4. A method of treating any mammal, preferably a human, affected by cancer or psoriasis which comprises administering to the affected individual a therapeutically effective amount of a compound as defined in claims 1 or 2.
5. A method according to claim 4 wherein the mammal is a human and he is affected by cancer.
6. A method according to claim 5 wherein the patient has a refractory cancer that does not respond favourably to other treatments.
7. The method of claim 5 wherein the cancer is selected from prostate cancer, breast cancer, hepatocellular carcinoma, melanoma, colorectal cancer, renal cancer, ovarian cancer, NSCL cancer, epithelial cancer, pancreatic cancer and tumors that overexpress the Her2/neu oncogene.
8. The use of a compound as defined in claim 1 or 2 in the manufacture of a medicament.
9. The use of a compound as defined . in claim 1 or 2 in the manufacture of a medicament for the treatment of cancer, psoriasis, viral infection or fungal infection.
10. A kit comprising separate containers containing a pharmaceutical composition comprising a compound as defined in claims 1 or 2 and a reconstituting agent.
11. A process for the preparation of a compound as defined in claims 1 or 2.
12. A process according to claim 11 characterized in that it uses 4-methylhexanoic acid as starting material.
13. A process according to claim 11 characterized in that it uses (4S)-methylhexanoic acid.
CA2501089A 2002-10-18 2003-10-20 4-methylhexanoic kahalaide f compound Expired - Fee Related CA2501089C (en)

Applications Claiming Priority (7)

Application Number Priority Date Filing Date Title
PCT/GB2002/004735 WO2003033012A1 (en) 2001-10-19 2002-10-18 Kahalalide compounds for use in cancer therapy
GBPCT/GB02/004735 2002-10-18
GBGB0304367.6A GB0304367D0 (en) 2003-02-26 2003-02-26 Methods for treating psoriasis
GB0304367.6 2003-02-26
GB0314725A GB0314725D0 (en) 2003-06-24 2003-06-24 New antitumoral compounds
GB0314725.3 2003-06-24
PCT/US2003/033207 WO2004035613A2 (en) 2002-10-18 2003-10-20 4-methylhexanoic kahalaide f compound

Publications (2)

Publication Number Publication Date
CA2501089A1 true CA2501089A1 (en) 2004-04-29
CA2501089C CA2501089C (en) 2012-07-17

Family

ID=32110555

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2501089A Expired - Fee Related CA2501089C (en) 2002-10-18 2003-10-20 4-methylhexanoic kahalaide f compound

Country Status (10)

Country Link
EP (1) EP1572726B1 (en)
JP (1) JP4430009B2 (en)
CN (2) CN101077885A (en)
BR (1) BR0315489A (en)
CA (1) CA2501089C (en)
ES (1) ES2357644T3 (en)
MX (1) MXPA05004133A (en)
NZ (1) NZ539093A (en)
WO (1) WO2004035613A2 (en)
ZA (1) ZA200502926B (en)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6274551B1 (en) * 1994-02-03 2001-08-14 Pharmamar, S.A. Cytotoxic and antiviral compound
GB0304367D0 (en) 2003-02-26 2003-04-02 Pharma Mar Sau Methods for treating psoriasis
US7507708B2 (en) 2003-02-26 2009-03-24 Pharma Mar, S.A.U. Antitumoral compounds
GB0321066D0 (en) 2003-09-09 2003-10-08 Pharma Mar Sau New antitumoral compounds
WO2009052379A2 (en) * 2007-10-19 2009-04-23 Pharma Mar, S.A. Improved antitumoral treatments
DE102008005097B4 (en) * 2008-01-18 2011-04-07 Leibnitz-Institut für Meereswissenschaften Antitumoral cyclodepsipeptides, their preparation and use
KR20100126479A (en) * 2008-03-07 2010-12-01 파르마 마르 에스.에이. Improved antitumoral treatments
WO2009135939A2 (en) * 2008-05-09 2009-11-12 Pharma Mar, S.A. Depsipeptide for use in cancer therapy
CA2817420C (en) 2010-11-12 2019-09-24 Pharma Mar, S.A. Combination therapy with an antitumor alkaloid
JOP20190254A1 (en) 2017-04-27 2019-10-27 Pharma Mar Sa Antitumoral compounds

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB9302046D0 (en) * 1993-02-03 1993-03-24 Pharma Mar Sa Antiumoral compound-v
US6274551B1 (en) * 1994-02-03 2001-08-14 Pharmamar, S.A. Cytotoxic and antiviral compound
SK286421B6 (en) * 2000-10-31 2008-09-05 Pharma Mar, S. A. Formulation of kahalalide F, kit, reconstituted and diluted solution comprising formulation and use
EP1435990A1 (en) * 2001-10-19 2004-07-14 Pharma Mar, S.A. Kahalalide compounds for use in cancer therapy

Also Published As

Publication number Publication date
WO2004035613A2 (en) 2004-04-29
ES2357644T3 (en) 2011-04-28
CN100591691C (en) 2010-02-24
NZ539093A (en) 2007-10-26
WO2004035613A3 (en) 2004-07-29
MXPA05004133A (en) 2005-10-05
EP1572726A2 (en) 2005-09-14
BR0315489A (en) 2005-08-23
JP2006517195A (en) 2006-07-20
CN101077885A (en) 2007-11-28
EP1572726B1 (en) 2010-12-08
CN1705677A (en) 2005-12-07
ZA200502926B (en) 2006-02-22
CA2501089C (en) 2012-07-17
JP4430009B2 (en) 2010-03-10

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Effective date: 20171020