CA2114156A1 - Elucidation and Synthesis of Selected Pentapeptides - Google Patents

Elucidation and Synthesis of Selected Pentapeptides

Info

Publication number
CA2114156A1
CA2114156A1 CA2114156A CA2114156A CA2114156A1 CA 2114156 A1 CA2114156 A1 CA 2114156A1 CA 2114156 A CA2114156 A CA 2114156A CA 2114156 A CA2114156 A CA 2114156A CA 2114156 A1 CA2114156 A1 CA 2114156A1
Authority
CA
Canada
Prior art keywords
pentapeptides
dolastatin
trifluoroacetate salt
peptides
elucidation
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
CA2114156A
Other languages
French (fr)
Other versions
CA2114156C (en
Inventor
George R. Pettit
Jayaram K. Srirangam
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.)
Arizona Board of Regents of University of Arizona
Original Assignee
Arizona Board of Regents of University of Arizona
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
Application filed by Arizona Board of Regents of University of Arizona filed Critical Arizona Board of Regents of University of Arizona
Publication of CA2114156A1 publication Critical patent/CA2114156A1/en
Application granted granted Critical
Publication of CA2114156C publication Critical patent/CA2114156C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

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
    • C07K5/02—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link
    • C07K5/0205—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -NH-(X)3-C(=0)-, e.g. statine or derivatives thereof
    • 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
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides

Abstract

The sea hare Dolabella auricularia has yielded many structurally distinct peptides which possess antineoplastic activity. Presently the compound denominated "dolastatin 10" represents then most important of such peptides because of its demonstrated potential as an anticancer drug.
The present invention relates to the systematic creation of five unique pentapeptides by selectively coupling a tripeptide - trifluoroacetate salt with a preselected dipeptide-trifluoroacetate salt which provide active molecules capable of emulating the measured therapeutic effect of dolastatin 10. The pentapeptides hereof have the structure shown below:
wherein R is selected from the following group of substituents:
CA002114156A 1993-01-26 1994-01-25 Elucidation and synthesis of selected pentapeptides Expired - Fee Related CA2114156C (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US08/009,296 US5780588A (en) 1993-01-26 1993-01-26 Elucidation and synthesis of selected pentapeptides
US009,296 1993-01-26

Publications (2)

Publication Number Publication Date
CA2114156A1 true CA2114156A1 (en) 1994-07-27
CA2114156C CA2114156C (en) 2001-01-02

Family

ID=21736778

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002114156A Expired - Fee Related CA2114156C (en) 1993-01-26 1994-01-25 Elucidation and synthesis of selected pentapeptides

Country Status (6)

Country Link
US (1) US5780588A (en)
EP (1) EP0612762B1 (en)
JP (1) JPH08119990A (en)
AT (1) ATE161270T1 (en)
CA (1) CA2114156C (en)
DE (1) DE69407322T2 (en)

Cited By (6)

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US7498298B2 (en) 2003-11-06 2009-03-03 Seattle Genetics, Inc. Monomethylvaline compounds capable of conjugation to ligands
US7659241B2 (en) 2002-07-31 2010-02-09 Seattle Genetics, Inc. Drug conjugates and their use for treating cancer, an autoimmune disease or an infectious disease
US7750116B1 (en) 2006-02-18 2010-07-06 Seattle Genetics, Inc. Antibody drug conjugate metabolites
US8343928B2 (en) 2005-07-07 2013-01-01 Seattle Genetics, Inc. Monomethylvaline compounds having phenylalanine side-chain replacements at the C-terminus
US8609105B2 (en) 2008-03-18 2013-12-17 Seattle Genetics, Inc. Auristatin drug linker conjugates
US8871720B2 (en) 2005-07-07 2014-10-28 Seattle Genetics, Inc. Monomethylvaline compounds having phenylalanine carboxy modifications at the C-terminus

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DE69829881T2 (en) * 1997-09-24 2006-03-09 Arizona Board Of Regents, Tempe SYNTHETIC ANTINEOPLASTIC ACTIVITIES DERIVED FROM DOLASTATIN 15 AND METHOD FOR THE PRODUCTION THEREOF
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CA2114156C (en) 2001-01-02
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ATE161270T1 (en) 1998-01-15
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EP0612762A1 (en) 1994-08-31
EP0612762B1 (en) 1997-12-17
DE69407322D1 (en) 1998-01-29

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