CA2501089A1 - 4-methylhexanoic kahalaide f compound - Google Patents
4-methylhexanoic kahalaide f compound Download PDFInfo
- 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
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract 10
- 201000004681 Psoriasis Diseases 0.000 claims abstract 3
- 238000011282 treatment Methods 0.000 claims abstract 3
- 238000000034 method Methods 0.000 claims 7
- 206010028980 Neoplasm Diseases 0.000 claims 5
- 201000011510 cancer Diseases 0.000 claims 5
- DIVCBWJKVSFZKJ-UHFFFAOYSA-N 4-methyl-hexanoic acid Chemical compound CCC(C)CCC(O)=O DIVCBWJKVSFZKJ-UHFFFAOYSA-N 0.000 claims 2
- 241000124008 Mammalia Species 0.000 claims 2
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 201000002528 pancreatic cancer Diseases 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 239000000651 prodrug Substances 0.000 claims 2
- 229940002612 prodrug Drugs 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 239000012453 solvate Substances 0.000 claims 2
- 206010006187 Breast cancer Diseases 0.000 claims 1
- 208000026310 Breast neoplasm Diseases 0.000 claims 1
- 201000009030 Carcinoma Diseases 0.000 claims 1
- 206010009944 Colon cancer Diseases 0.000 claims 1
- 208000001333 Colorectal Neoplasms Diseases 0.000 claims 1
- 101150029707 ERBB2 gene Proteins 0.000 claims 1
- 206010017533 Fungal infection Diseases 0.000 claims 1
- 102100021888 Helix-loop-helix protein 1 Human genes 0.000 claims 1
- 101000897691 Homo sapiens Helix-loop-helix protein 1 Proteins 0.000 claims 1
- 208000008839 Kidney Neoplasms Diseases 0.000 claims 1
- 208000031888 Mycoses Diseases 0.000 claims 1
- 108700020796 Oncogene Proteins 0.000 claims 1
- 206010033128 Ovarian cancer Diseases 0.000 claims 1
- 206010061535 Ovarian neoplasm Diseases 0.000 claims 1
- 206010060862 Prostate cancer Diseases 0.000 claims 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 1
- 206010070308 Refractory cancer Diseases 0.000 claims 1
- 206010038389 Renal cancer Diseases 0.000 claims 1
- 208000036142 Viral infection Diseases 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 206010073071 hepatocellular carcinoma Diseases 0.000 claims 1
- 231100000844 hepatocellular carcinoma Toxicity 0.000 claims 1
- 201000010982 kidney cancer Diseases 0.000 claims 1
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims 1
- 201000001441 melanoma Diseases 0.000 claims 1
- 208000008443 pancreatic carcinoma Diseases 0.000 claims 1
- 208000016691 refractory malignant neoplasm Diseases 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- 239000003981 vehicle Substances 0.000 claims 1
- 230000009385 viral infection Effects 0.000 claims 1
- 230000000259 anti-tumor effect Effects 0.000 abstract 2
- RCGXNDQKCXNWLO-WLEIXIPESA-N (2r)-n-[(2s)-5-amino-1-[[(2r,3r)-1-[[(3s,6z,9s,12r,15r,18r,19s)-9-benzyl-15-[(2r)-butan-2-yl]-6-ethylidene-19-methyl-2,5,8,11,14,17-hexaoxo-3,12-di(propan-2-yl)-1-oxa-4,7,10,13,16-pentazacyclononadec-18-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-1-oxopent Chemical class N([C@@H](CCCN)C(=O)N[C@H]([C@H](C)CC)C(=O)N[C@H]1C(N[C@@H](C(=O)N[C@@H](C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)NC(/C(=O)N[C@H](C(=O)O[C@H]1C)C(C)C)=C\C)C(C)C)[C@H](C)CC)=O)C(=O)[C@H]1CCCN1C(=O)[C@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](NC(=O)CCCC(C)C)C(C)C)[C@@H](C)O)C(C)C)C(C)C RCGXNDQKCXNWLO-WLEIXIPESA-N 0.000 abstract 1
- 230000000840 anti-viral effect Effects 0.000 abstract 1
- 229940121375 antifungal agent Drugs 0.000 abstract 1
- 239000003429 antifungal agent Substances 0.000 abstract 1
- 229930194861 kahalalide Natural products 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
- C07K7/08—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)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biophysics (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Zoology (AREA)
- Gastroenterology & Hepatology (AREA)
- Toxicology (AREA)
- Immunology (AREA)
- Virology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Dermatology (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.
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.
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.
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBPCT/GB02/004735 | 2002-10-18 | ||
| PCT/GB2002/004735 WO2003033012A1 (en) | 2001-10-19 | 2002-10-18 | Kahalalide compounds for use in cancer therapy |
| GB0304367.6 | 2003-02-26 | ||
| GBGB0304367.6A GB0304367D0 (en) | 2003-02-26 | 2003-02-26 | Methods for treating psoriasis |
| 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 (11)
| 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 |
| AU2008312400A1 (en) * | 2007-10-19 | 2009-04-23 | Albert Einstein College Of Medicine Of Yeshiva University | Improved antitumoral treatments |
| DE102008005097B4 (en) * | 2008-01-18 | 2011-04-07 | Leibnitz-Institut für Meereswissenschaften | Antitumoral cyclodepsipeptides, their preparation and use |
| CA2717117A1 (en) * | 2008-03-07 | 2009-09-11 | Pharma Mar, S.A. | Improved antitumoral treatments |
| WO2009135939A2 (en) * | 2008-05-09 | 2009-11-12 | Pharma Mar, S.A. | Depsipeptide for use in cancer therapy |
| HUE042801T2 (en) * | 2010-11-12 | 2019-07-29 | Pharma Mar Sa | Combination therapy with mitosis inhibitor |
| JOP20190254A1 (en) | 2017-04-27 | 2019-10-27 | Pharma Mar Sa | Antitumoral compounds |
| PH12022551216A1 (en) | 2019-11-21 | 2023-07-17 | Pharma Mar Sa | Methods of treating small cell lung cancer with lurbinectedin formulations |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6178719A (en) * | 1984-09-25 | 1986-04-22 | Tanabe Seiyaku Co Ltd | Comprehensive infusion agent |
| US6274551B1 (en) * | 1994-02-03 | 2001-08-14 | Pharmamar, S.A. | Cytotoxic and antiviral compound |
| GB9302046D0 (en) * | 1993-02-03 | 1993-03-24 | Pharma Mar Sa | Antiumoral compound-v |
| IL155297A0 (en) * | 2000-10-31 | 2003-11-23 | Pharma Mar Sa | Kahalalide f formulation |
| WO2003033012A1 (en) * | 2001-10-19 | 2003-04-24 | Pharma Mar, S.A. | Kahalalide compounds for use in cancer therapy |
-
2003
- 2003-10-20 MX MXPA05004133A patent/MXPA05004133A/en active IP Right Grant
- 2003-10-20 JP JP2005501483A patent/JP4430009B2/en not_active Expired - Fee Related
- 2003-10-20 WO PCT/US2003/033207 patent/WO2004035613A2/en not_active Ceased
- 2003-10-20 BR BR0315489-0A patent/BR0315489A/en not_active IP Right Cessation
- 2003-10-20 CN CNA2007101122538A patent/CN101077885A/en active Pending
- 2003-10-20 EP EP03779140A patent/EP1572726B1/en not_active Expired - Lifetime
- 2003-10-20 ES ES03779140T patent/ES2357644T3/en not_active Expired - Lifetime
- 2003-10-20 CA CA2501089A patent/CA2501089C/en not_active Expired - Fee Related
- 2003-10-20 NZ NZ539093A patent/NZ539093A/en not_active IP Right Cessation
- 2003-10-20 CN CN200380101647A patent/CN100591691C/en not_active Expired - Fee Related
-
2005
- 2005-04-11 ZA ZA200502926A patent/ZA200502926B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CA2501089C (en) | 2012-07-17 |
| EP1572726B1 (en) | 2010-12-08 |
| BR0315489A (en) | 2005-08-23 |
| JP2006517195A (en) | 2006-07-20 |
| WO2004035613A3 (en) | 2004-07-29 |
| CN101077885A (en) | 2007-11-28 |
| MXPA05004133A (en) | 2005-10-05 |
| CN100591691C (en) | 2010-02-24 |
| CN1705677A (en) | 2005-12-07 |
| ES2357644T3 (en) | 2011-04-28 |
| ZA200502926B (en) | 2006-02-22 |
| JP4430009B2 (en) | 2010-03-10 |
| NZ539093A (en) | 2007-10-26 |
| WO2004035613A2 (en) | 2004-04-29 |
| EP1572726A2 (en) | 2005-09-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20171020 |