CA2115355A1 - Novel tetrapeptide derivative - Google Patents

Novel tetrapeptide derivative

Info

Publication number
CA2115355A1
CA2115355A1 CA002115355A CA2115355A CA2115355A1 CA 2115355 A1 CA2115355 A1 CA 2115355A1 CA 002115355 A CA002115355 A CA 002115355A CA 2115355 A CA2115355 A CA 2115355A CA 2115355 A1 CA2115355 A1 CA 2115355A1
Authority
CA
Canada
Prior art keywords
group
hydrogen atom
represent
lower alkyl
see formula
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
CA002115355A
Other languages
French (fr)
Other versions
CA2115355C (en
Inventor
Kyoichi Sakakibara
Masaaki Gondo
Koichi Miyazaki
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.)
Aska Pharmaceutical Co Ltd
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
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=26525532&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=CA2115355(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Individual filed Critical Individual
Publication of CA2115355A1 publication Critical patent/CA2115355A1/en
Application granted granted Critical
Publication of CA2115355C publication Critical patent/CA2115355C/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
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06—Dipeptides
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
    • C07K7/02—Linear peptides containing at least one abnormal peptide link
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides

Abstract

A tetrapeptide derivative represented by the following formula or a salt thereof has a higher cyto-static activity than dolastatin 10, and is useful as an antitumor agent:

(see above formula I) wherein, R1, R2, R3 and R4 are the same or different and each represent a hydrogen atom, a lower alkyl group or an aralkyl group;

Q represents (see formula II) or a group of -A2-R7, wherein, A1 represents a direct bond or (see formula III) Y represents a hydrogen atom or -COR6, R5 represents a hydrogen atom, a lower alkyl group or an aralkyl group, R6 represents a hydroxyl group, a lower alkoxy group, an aralkyloxy group or (see formula IV) wherein, R8 and R9 are the same or different and each represent a hydrogen atom, a lower alkyl group, a phenyl group or a 4- to 7-membered heterocyclic group containing one or two hetero atoms selected from S, O
and N, or alternatively R8 and R9 may combine together with the nitrogen atom to which they are bonded to form a 4- to 7-membered heterocyclic ring optionally further containing one hetero atom selected from S, O and N, A2 represents a direct bond or a lower alkylene group, and R7 represents a cycloalkyl group, an aryl group or an indolyl group, provided that the case is excluded where both R1 and R2 represent isopropyl groups, R3 repre-sents a sec-butyl group, R4 represents a methyl group, and Q represents an .alpha.-(2-thiazolyl) phene-thyl group.
CA002115355A 1991-08-09 1992-08-06 Novel tetrapeptide derivative Expired - Fee Related CA2115355C (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
JP223534/1991 1991-08-09
JP22353491 1991-08-09
JP225391/1991 1991-08-12
JP22539191 1991-08-12
PCT/JP1992/001005 WO1993003054A1 (en) 1991-08-09 1992-08-06 Novel tetrapeptide derivative

Publications (2)

Publication Number Publication Date
CA2115355A1 true CA2115355A1 (en) 1993-02-18
CA2115355C CA2115355C (en) 2007-09-11

Family

ID=26525532

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002115355A Expired - Fee Related CA2115355C (en) 1991-08-09 1992-08-06 Novel tetrapeptide derivative

Country Status (13)

Country Link
US (2) US6004934A (en)
EP (2) EP0934950B1 (en)
JP (1) JP2618597B2 (en)
KR (2) KR0185440B1 (en)
AT (2) ATE190983T1 (en)
AU (2) AU662551B2 (en)
CA (1) CA2115355C (en)
DE (2) DE69230824T2 (en)
DK (2) DK0934950T3 (en)
ES (2) ES2144421T3 (en)
GR (1) GR3033397T3 (en)
SG (1) SG87056A1 (en)
WO (1) WO1993003054A1 (en)

Families Citing this family (55)

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HUT71398A (en) * 1992-05-20 1995-11-28 Basf Ag Derivatives of dolastatin
PL178766B1 (en) * 1992-12-16 2000-06-30 Basf Ag Novel peptides, method of obtaining them and their application
US5767237A (en) * 1993-10-01 1998-06-16 Teikoku Hormone Mfg. Co., Ltd. Peptide derivatives
US5599902A (en) * 1994-11-10 1997-02-04 Arizona Board Of Regents Acting On Behalf Of Arizona State University Cancer inhibitory peptides
US5663149A (en) * 1994-12-13 1997-09-02 Arizona Board Of Regents Acting On Behalf Of Arizona State University Human cancer inhibitory pentapeptide heterocyclic and halophenyl amides
CN1113066C (en) * 1995-04-21 2003-07-02 帝国脏器制药株式会社 Novel peptide derivatives
US5807984A (en) * 1995-11-09 1998-09-15 Basf Aktienegesellschaft Oligopeptides, the preparation and use thereof
US20010009901A1 (en) 1996-12-11 2001-07-26 Basf Aktiengesellschaft Germany Antineoplastic peptides
US5939527A (en) * 1996-07-30 1999-08-17 Basf Aktiengesellschaft Tetrapeptides as antitumor agents
US5741892A (en) * 1996-07-30 1998-04-21 Basf Aktiengesellschaft Pentapeptides as antitumor agents
US5965537A (en) * 1997-03-10 1999-10-12 Basf Aktiengesellschaft Dolastatin 15 derivatives with carbonyl and heterocyclic functionalities at the C-terminus
US6103698A (en) 1997-03-13 2000-08-15 Basf Aktiengesellschaft Dolastatin-15 derivatives in combination with taxanes
US6143721A (en) 1997-07-18 2000-11-07 Basf Aktiengesellschaft Dolastatin 15 derivatives
US6686445B1 (en) 1997-09-24 2004-02-03 Arizona Board Of Regents, Acting For And On Behalf Of Arizona State University Synthetic antineoplastic agents derived from dolastatin 15 and methods of making same
CA2298639C (en) * 1997-09-24 2005-07-05 Erik J. Flahive Synthetic antineoplastic agents derived from dolastatin 15 and methods of making same
US6015790A (en) * 1997-10-06 2000-01-18 Basf Aktiengesellschaft Methods and compositions for treating rheumatoid arthritis
US5985837A (en) * 1998-07-08 1999-11-16 Basf Aktiengesellschaft Dolastatin 15 derivatives
US6323315B1 (en) * 1999-09-10 2001-11-27 Basf Aktiengesellschaft Dolastatin peptides
CA2385528C (en) 1999-10-01 2013-12-10 Immunogen, Inc. Compositions and methods for treating cancer using immunoconjugates and chemotherapeutic agents
AU1730701A (en) * 1999-12-07 2001-06-18 Santen Pharmaceutical Co. Ltd. Rheumatism remedy containing tetrapeptide derivative as active ingredient
US6884869B2 (en) * 2001-04-30 2005-04-26 Seattle Genetics, Inc. Pentapeptide compounds and uses related thereto
US7256257B2 (en) * 2001-04-30 2007-08-14 Seattle Genetics, Inc. Pentapeptide compounds and uses related thereto
KR20010079252A (en) * 2001-06-27 2001-08-22 홍진의 Drum filter of which drum is wrinkled
JP4060794B2 (en) * 2001-09-20 2008-03-12 あすか製薬株式会社 Crystals of tetrapeptide derivatives
ES2544527T3 (en) 2002-07-31 2015-09-01 Seattle Genetics, Inc. Drug conjugates and their use to treat cancer, an autoimmune disease or an infectious disease
ZA200603619B (en) 2003-11-06 2008-10-29 Seattle Genetics Inc Monomethylvaline compounds capable of conjugation to ligands
WO2006132670A2 (en) * 2004-11-12 2006-12-14 Seattle Genetics, Inc. Auristatins having an aminobenzoic acid unit at the n terminus
EP1883627B1 (en) 2005-05-18 2018-04-18 Pharmascience Inc. Bir domain binding compounds
AU2006269422B2 (en) 2005-07-07 2012-12-06 Seagen Inc. Monomethylvaline compounds having phenylalanine side-chain modifications at the C-terminus
WO2007008848A2 (en) 2005-07-07 2007-01-18 Seattle Genetics, Inc. Monomethylvaline compounds having phenylalanine carboxy modifications at the c-terminus
US7750116B1 (en) * 2006-02-18 2010-07-06 Seattle Genetics, Inc. Antibody drug conjugate metabolites
EP2024362A4 (en) 2006-05-16 2012-01-25 Pharmascience Inc Iap bir domain binding compounds
US9845355B2 (en) 2007-07-16 2017-12-19 Genentech, Inc. Humanized anti-CD79b antibodies and immunoconjugates and methods of use
PL2474557T3 (en) 2007-07-16 2015-02-27 Genentech Inc Anti-CD79b antibodies and immunoconjugates and methods of use
US20090035848A1 (en) * 2007-08-03 2009-02-05 Robert Hickey Moving bed biofilm reactor (mbbr) system for conversion of syngas components to liquid products
RU2553566C2 (en) 2008-01-31 2015-06-20 Дженентек, Инк. ANTI-CD79b ANTIBODIES AND IMMUNOCONJUGATES AND METHODS FOR USING THEM
CA2718942A1 (en) * 2008-03-18 2009-09-24 Seattle Genetics, Inc. Auristatin drug linker conjugates
AU2011214057B2 (en) 2010-02-12 2016-11-17 Pharmascience Inc. IAP BIR domain binding compounds
ES2657014T3 (en) 2011-11-17 2018-03-01 Pfizer Inc. Cytotoxic peptides and antibody drug conjugates thereof
ES2604766T3 (en) * 2012-09-20 2017-03-09 Celltrion, Inc. Dolastatin-10 derivative, its production process and anticancer drug composition containing the same
ES2701076T3 (en) 2012-11-24 2019-02-20 Hangzhou Dac Biotech Co Ltd Hydrophilic linkers and their uses for the conjugation of drugs to molecules that bind to cells
CA2930614A1 (en) 2013-12-17 2015-06-25 Novartis Ag Cytotoxic peptides and conjugates thereof
CN114262344A (en) 2014-02-28 2022-04-01 杭州多禧生物科技有限公司 Charged linkers and their use in conjugation reactions
RU2747989C2 (en) * 2014-05-28 2021-05-18 Эдженсис, Инк. Derivatives of dolaproin-dolaizolein peptides
EA201692530A1 (en) 2014-06-13 2017-07-31 Новартис Аг CYTOTOXIC PEPTIDES AND THEIR CONJUGATES
PL3262071T3 (en) 2014-09-23 2020-08-10 F. Hoffmann-La Roche Ag Method of using anti-cd79b immunoconjugates
NZ739830A (en) 2015-07-12 2021-12-24 Hangzhou Dac Biotech Co Ltd Bridge linkers for conjugation of cell-binding molecules
US9839687B2 (en) 2015-07-15 2017-12-12 Suzhou M-Conj Biotech Co., Ltd. Acetylenedicarboxyl linkers and their uses in specific conjugation of a cell-binding molecule
AU2016297786A1 (en) 2015-07-24 2018-02-08 Noeleen Melody Quinstatin compounds
WO2017058808A1 (en) * 2015-10-02 2017-04-06 Sirenas Llc Anti-cancer compounds and conjugates thereof
WO2017170637A1 (en) * 2016-03-29 2017-10-05 東レ株式会社 Peptide derivative and use thereof
KR20220147721A (en) 2016-11-14 2022-11-03 항저우 디에이씨 바이오테크 씨오, 엘티디 Conjugation linkers, cell binding molecule-drug conjugates containing the likers, methods of making and uses such conjugates with the linkers
EP4051691A4 (en) * 2019-10-28 2023-11-08 Ariel Scientific Innovations Ltd. Dolastatin 10 analog
AU2022338463A1 (en) 2021-09-03 2024-03-21 Toray Industries, Inc. Pharmaceutical composition for cancer treatment and/or prevention

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5017691A (en) * 1986-07-03 1991-05-21 Schering Corporation Mammalian interleukin-4
US4816444A (en) * 1987-07-10 1989-03-28 Arizona Board Of Regents, Arizona State University Cell growth inhibitory substance
US4978744A (en) * 1989-01-27 1990-12-18 Arizona Board Of Regents Synthesis of dolastatin 10
US5635483A (en) * 1992-12-03 1997-06-03 Arizona Board Of Regents Acting On Behalf Of Arizona State University Tumor inhibiting tetrapeptide bearing modified phenethyl amides
US6034065A (en) * 1992-12-03 2000-03-07 Arizona Board Of Regents Elucidation and synthesis of antineoplastic tetrapeptide phenethylamides of dolastatin 10

Also Published As

Publication number Publication date
DK0598129T3 (en) 2000-07-03
ATE215962T1 (en) 2002-04-15
ES2172069T3 (en) 2002-09-16
DE69232552D1 (en) 2002-05-16
SG87056A1 (en) 2002-03-19
EP0598129A4 (en) 1995-10-25
DK0934950T3 (en) 2002-07-29
DE69230824T2 (en) 2000-07-27
EP0934950A1 (en) 1999-08-11
EP0598129A1 (en) 1994-05-25
CA2115355C (en) 2007-09-11
DE69230824D1 (en) 2000-04-27
DE69232552T2 (en) 2002-10-31
AU2001095A (en) 1995-07-20
KR0185440B1 (en) 1999-04-01
KR100202474B1 (en) 1999-06-15
US6004934A (en) 1999-12-21
AU673487B2 (en) 1996-11-07
AU2415292A (en) 1993-03-02
WO1993003054A1 (en) 1993-02-18
JP2618597B2 (en) 1997-06-11
EP0598129B1 (en) 2000-03-22
ATE190983T1 (en) 2000-04-15
US5654399A (en) 1997-08-05
ES2144421T3 (en) 2000-06-16
GR3033397T3 (en) 2000-09-29
AU662551B2 (en) 1995-09-07
EP0934950B1 (en) 2002-04-10

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