WO2004010957B1 - Drug conjugates and their use for treating cancer, an autoimmune disease or an infectious disease - Google Patents

Drug conjugates and their use for treating cancer, an autoimmune disease or an infectious disease

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Publication number
WO2004010957B1
WO2004010957B1 PCT/US2003/024209 US0324209W WO2004010957B1 WO 2004010957 B1 WO2004010957 B1 WO 2004010957B1 US 0324209 W US0324209 W US 0324209W WO 2004010957 B1 WO2004010957 B1 WO 2004010957B1
Authority
WO
WIPO (PCT)
Prior art keywords
alkyl
compound
pharmaceutically acceptable
solvate
acceptable salt
Prior art date
Application number
PCT/US2003/024209
Other languages
French (fr)
Other versions
WO2004010957A3 (en
WO2004010957A2 (en
Inventor
Peter D Senter
Svetlana Doronina
Brian E Toki
Original Assignee
Seattle Genetics Inc
Peter D Senter
Svetlana Doronina
Brian E Toki
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 to SI200332051T priority Critical patent/SI1545613T1/en
Priority to DK03772186.7T priority patent/DK1545613T3/en
Priority to AT03772186T priority patent/ATE516818T1/en
Priority to US10/522,911 priority patent/US7659241B2/en
Priority to AU2003263964A priority patent/AU2003263964C1/en
Priority to CA2494105A priority patent/CA2494105C/en
Priority to EP03772186A priority patent/EP1545613B9/en
Priority to JP2004524294A priority patent/JP4741838B2/en
Application filed by Seattle Genetics Inc, Peter D Senter, Svetlana Doronina, Brian E Toki filed Critical Seattle Genetics Inc
Publication of WO2004010957A2 publication Critical patent/WO2004010957A2/en
Publication of WO2004010957A3 publication Critical patent/WO2004010957A3/en
Publication of WO2004010957B1 publication Critical patent/WO2004010957B1/en
Priority to US12/408,646 priority patent/US7829531B2/en
Priority to US12/621,406 priority patent/US7851437B2/en
Priority to AU2010201459A priority patent/AU2010201459B2/en
Priority to US12/880,028 priority patent/US8906376B2/en
Priority to FR12C0066C priority patent/FR12C0066I2/en
Priority to BE2012C047C priority patent/BE2012C047I2/fr
Priority to CY2013004C priority patent/CY2013004I2/en
Priority to HUS1300002C priority patent/HUS1300002I1/en

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
    • A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
    • A61K47/62—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being a protein, peptide or polyamino acid
    • A61K47/64—Drug-peptide, drug-protein or drug-polyamino acid conjugates, i.e. the modifying agent being a peptide, protein or polyamino acid which is covalently bonded or complexed to a therapeutically active agent
    • A61K47/642—Drug-peptide, drug-protein or drug-polyamino acid conjugates, i.e. the modifying agent being a peptide, protein or polyamino acid which is covalently bonded or complexed to a therapeutically active agent the peptide or protein in the drug conjugate being a cytokine, e.g. IL2, chemokine, growth factors or interferons being the inactive part of the conjugate
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
    • A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
    • A61K47/62—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being a protein, peptide or polyamino acid
    • A61K47/64—Drug-peptide, drug-protein or drug-polyamino acid conjugates, i.e. the modifying agent being a peptide, protein or polyamino acid which is covalently bonded or complexed to a therapeutically active agent
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
    • A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
    • A61K47/68—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an antibody, an immunoglobulin or a fragment thereof, e.g. an Fc-fragment
    • A61K47/6801—Drug-antibody or immunoglobulin conjugates defined by the pharmacologically or therapeutically active agent
    • A61K47/6803—Drugs conjugated to an antibody or immunoglobulin, e.g. cisplatin-antibody conjugates
    • A61K47/6811—Drugs conjugated to an antibody or immunoglobulin, e.g. cisplatin-antibody conjugates the drug being a protein or peptide, e.g. transferrin or bleomycin
    • A61K47/6817—Toxins
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
    • A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
    • A61K47/68—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an antibody, an immunoglobulin or a fragment thereof, e.g. an Fc-fragment
    • A61K47/6835—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an antibody, an immunoglobulin or a fragment thereof, e.g. an Fc-fragment the modifying agent being an antibody or an immunoglobulin bearing at least one antigen-binding site
    • A61K47/6851—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an antibody, an immunoglobulin or a fragment thereof, e.g. an Fc-fragment the modifying agent being an antibody or an immunoglobulin bearing at least one antigen-binding site the antibody targeting a determinant of a tumour cell
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
    • A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
    • A61K47/68—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an antibody, an immunoglobulin or a fragment thereof, e.g. an Fc-fragment
    • A61K47/6835—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an antibody, an immunoglobulin or a fragment thereof, e.g. an Fc-fragment the modifying agent being an antibody or an immunoglobulin bearing at least one antigen-binding site
    • A61K47/6851—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an antibody, an immunoglobulin or a fragment thereof, e.g. an Fc-fragment the modifying agent being an antibody or an immunoglobulin bearing at least one antigen-binding site the antibody targeting a determinant of a tumour cell
    • A61K47/6867—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an antibody, an immunoglobulin or a fragment thereof, e.g. an Fc-fragment the modifying agent being an antibody or an immunoglobulin bearing at least one antigen-binding site the antibody targeting a determinant of a tumour cell the tumour determinant being from a cell of a blood cancer
    • 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
    • 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
    • A61P37/00—Drugs for immunological or allergic disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
    • 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

Abstract

Drug-Linker-Ligand Conjugates are disclosed in which a Drug is linked to a Ligand via a peptide-based Linker unit. In one embodiment, the Ligand is an Antibody. Drug-Linker compounds and Drug compounds are also disclosed. Methods for treating cancer, an autoimmune disease or an infectious disease using the compounds and compositions of the invention are also disclosed.

Claims

AMENDED CLAIMS received by the International Bureau onl6 June 2004 : claims 1,5, 7 are amended, 93-119 are added, claims 2-4,6 and 8-92 are unchanged.
R6 is selected from -H and -Cι-C8 alkyl;
R7 is selected from -H, -Cι-C8 alkyl, -C3-C8 carbocycle, -O- -Cs alkyl), aryl, -Cι-C8 alkyl-aryl, -Cι-C8 alkyl-(C3-C8 carbocycle), -C3-C8 heterocycle and -Cι-C8 alkyl-(C3-C8 heterocycle); each R is independently selected from -H, -OH, -Cι-C8 alkyl, -C3-C8 carbocycle and -O-(C!-C8 alkyl);
R9 is selected from -H and - - alkyl; R10 is selected from
Figure imgf000002_0001
Z is -O-, -S-, -NH-
Figure imgf000002_0002
R11 is selected from -H, -OH, -NH2, -NHR14, -N(R14)2, -C C8 alkyl, -C3-C8 carbocycle, -O-(C!-C8 alkyl), -aryl, -Ci-C8 alkyl-aryl, -Cι-C8 alkyl-(C3-C8 carbocycle), -C3- C8 heterocycle and -CrC8 alkyl-(C3-C8 heterocycle); or R11 is an oxygen atom which forms a carbonyl unit (C=O) with the carbon atom to which it is attached and a hydrogen atom on this carbon atom is replaced by one of the bonds in the (C=O) double bond; each R is independently selected from -aryl and -C3-C8 heterocycle;
R13 is selected from -H, -OH, -NH2, -NHR14, -N(R14)2, - -Cs alkyl, -C3-C8 carbocycle, -O-(Ci-C8 alkyl), -aryl, -Cι-C8 alkyl-aryl, -Cι-C8 alkyl-(C3-C8 carbocycle), C3- C8 heterocycle and -Cι-8 alkyl-(C3-C8 heterocycle); and
Each R14 is independently -H or - -Cs alkyl.
2. The compound of claim 1 wherein w is an integer ranging from 2 to 12.
A compound of the formula lb:
Figure imgf000002_0003
lb or a pharmaceutically acceptable salt or solvate thereof
279
Figure imgf000003_0001
Z is -O-, -S-, -NH- or -N(R14)-;
R11 is selected from -H, -OH, -NH2, -NHR14, -N(R14)2, -d-C8 alkyl, -C3-C8 carbocycle, -O-(Cι-C8 alkyl), -aryl, -Cι-C8 alkyl-aryl, -Cι-C8 alkyl-(C3-C8 carbocycle), -C3- C8 heterocycle and -Ci-C8 alkyl-(C3-C8 heterocycle); or R11 is an oxygen atom which forms a carbonyl unit (C=O) with the carbon atom to which it is attached and a hydrogen atom on this carbon atom is replaced by one of the bonds in the (C=O) double bond; each R12 is independently selected from -aryl and -C3-C8 heterocycle;
R13 is selected from -H, -OH, -NH2, -NHR14, -N(R14)2, -C C8 alkyl, -C3-C8 carbocycle, -©-( -Cs alkoxy), -aryl, - -Cs alkyl-aryl, - - alkyl-(C3-C8 carbocycle), C3-C8 heterocycle and -Cι-C8 alkyl-(C3-C8 heterocycle); and each R14 is independently -H or - -Cs alkyl.
The compound of claim 5 wherein w is an integer ranging from 2 to 12.
7. A compound or a pharmaceutically acceptable salt or solvate of the compound of claim 1 where -D is a Drug unit having the structure
Figure imgf000003_0002
or a pharmaceutically acceptable salt or solvate thereof, wherein, independently at each location:
R2 is selected from -H and -methyl;
R3 is selected from -H, -methyl, and -isopropyl;
R4 is selected from -H and -methyl; R5 is selected from -isopropyl, -isobutyl, -sec-butyl, -methyl and -t-butyl or R4 and R5 join, have the formula - (CRaR )n- where Ra and Rb are independently selected from -H, -Cι-C8 alkyl, and -C3-C8 carbocycle, and n is selected from 2, 3, 4, 5 and 6, and form a ring with the carbon atom to which they are attached;
R6 is selected from -H and -methyl; each R8 is independently selected from -OH, -methoxy and -ethoxy;
R10 is selected from
Figure imgf000004_0001
R24 is selected from H and -C(O)R25-; wherein R25 is selected from -Q- alkyl, -C3-C8 carbocycle, -aryl, -Cι-C alkyl-aryl, - -Cs alkyl-(C3-C8 carbocycle), -C3-C8 heterocycle and -Cι-C8 alkyl-(C3-C8 heterocycle); Z is -O-, -NH-, -OC(O)-, -NHC(O)-, -NR28C(O)- ; where R28 is selected from -H and -Cι-C8 alkyl; n is 0 or 1; and
R27 is selected from -H, -N3, - - alkyl, -C -C8 carbocycle, -aryl, -Q-Cs alkyl-aryl, -Ci-C8 alkyl-(C3-C8 carbocycle), -C3-C8 heterocycle and -Ci-C8 alkyl-(C -C8 heterocycle) when n is 0; and R27 is selected from -H, -C Cs alkyl, -C3-C8 carbocycle, - aryl, - -Cs alkyl-aryl, -Cι-C8 alkyl-(C3-C8 carbocycle), -C3-C8 heterocycle and - -Cs alkyl-(C3-C8 heterocycle) when n is 1.
8. A compound or a pharmaceutically acceptable salt or solvate of the compound of claim 1 where -D is a Drug unit having the structure
Figure imgf000004_0002
9. A compound or a pharmaceutically acceptable salt or solvate of the compound of claim 1 where -D is a Drug unit having the structure or a pharmaceutically acceptable salt or solvate thereof.
90. A compound having the structure
Figure imgf000005_0001
or a pharmaceutically acceptable salt or solvate thereof.
91. A compound having the structure
Figure imgf000005_0002
or a pharmaceutically acceptable salt or solvate thereof.
92. The compound or a pharmaceutically acceptable salt or solvate thereof of any one of claims 1, 3, 5, 32, 34, 35, 36, 37, 38, 43 or 44, in an isolated or a purified form.
93. A compound having the structure
Figure imgf000005_0003
or a pharmaceutically acceptable salt or solvate thereof, where p ranges from about 7 to about 9.
94. A compound having the structure
Figure imgf000006_0001
or a pharmaceutically acceptable salt or solvate thereof, where p ranges from about 7 to about 9
95. A compound having the structure
Figure imgf000006_0002
or a pharmaceutically acceptable salt or solvate thereof, where p ranges from about 7 to about 9; and L is an anti-CD20 antibody.
96. The compound of claim 95 wherein L is rituximab.
97. A compound having the structure
Figure imgf000006_0003
or a pharmaceutically acceptable salt or solvate thereof, where p ranges from about 7 to about 9; and L is an anti-CD40 antibody.
98. The compound of claim 97 wherein L is S2C6.
99. A compound having the structure
Figure imgf000007_0001
or a pharmaceutically acceptable salt or solvate thereof, where p ranges from about 7 to about 9; and L is an anti-CD20 antibody.
100. The compound of claim 99 wherein L is rituximab.
101. A compound having the structure
Figure imgf000007_0002
or a pharmaceutically acceptable salt or solvate thereof, where p ranges from about 7 to about 9; and L is an anti-CD40 antibody.
102. The compound of claim 101 wherein L is S2C6.
103. A compound having the structure
Figure imgf000007_0003
or a pharmaceutically acceptable salt or solvate thereof, where p ranges from about 7 to about 9; and L is an anti-CD20 antibody.
104. The compound of claim 103 wherein L is rituximab.
105. A compound having the structure
Figure imgf000008_0001
or a pharmaceutically acceptable salt or solvate thereof, where p ranges from about 7 to about 9; and L is an anti-CD40 antibody.
106. The compound of claim 105 wherein L is S2C6.
107. A compound having the structure
Figure imgf000008_0002
or a pharmaceutically acceptable salt or solvate thereof, where p ranges from about 7 to about 9; and L is an anti-CD20 antibody.
108. The compound of claim 107 wherein L is rituximab.
109. A compound having the structure
Figure imgf000009_0001
or a pharmaceutically acceptable salt or solvate thereof, where p ranges from about 7 to about 9; and L is an anti-CD40 antibody.
110. The compound of claim 109 wherein L is S2C6.
111. A composition comprising an effective amount of a compound or a pharmaceutically acceptable salt or solvate thereof of any one of claims 77-91, 93-95, 97, 99, 101, 103, 105, 107 and 109 and a pharmaceutically acceptable carrier or vehicle.
112. A method for killing or inhibiting the multiplication of a tumor cell or cancer cell comprising administering to an animal in need thereof a therapeutically effective amount of a compound or a pharmaceutically acceptable salt or solvate thereof of any one of claims 77-91, 93-95, 97, 99, 101, 103, 105, 107 and 109.
113. A method for treating cancer, comprising administering to an animal in need thereof an effective amount of a compound or a pharmaceutically acceptable salt or solvate of the compound of any one of claims 77-91, 93-95, 97, 99, 101, 103, 105, 107 and 109.
114. A method for treating an autoimmune disease, comprising administering to an animal in need thereof an effective amount of a compound or a pharmaceutically acceptable salt or solvate of the compound of any one of claims 77-91, 93-95, 97, 99, 101, 103, 105, 107 and 109.
115. A method for treating an infectious disease, comprising administering to an animal in need thereof an effective amount of a compound or a pharmaceutically acceptable salt or solvate of the compound of any one of claims 77-91, 93-95, 97, 99, 101, 103, 105, 107 and 109.
116. The method of claim 113 further comprising administering to the animal an effective amount of an anticancer agent.
117. The method of claim 114 further comprising administering to the animal an effective amount of an immunosuppressant agent.
118. The method of claim 115 further comprising administering to the animal an effective amount of an anti-infectious agent.
119. The compound or a pharmaceutically acceptable salt or solvate thereof of any one of claims 77-91, 93-95, 97, 99, 101, 103, 105, 107 and 109, in an isolated or a purified form.
PCT/US2003/024209 2002-07-31 2003-07-31 Drug conjugates and their use for treating cancer, an autoimmune disease or an infectious disease WO2004010957A2 (en)

Priority Applications (16)

Application Number Priority Date Filing Date Title
DK03772186.7T DK1545613T3 (en) 2002-07-31 2003-07-31 Auristatin conjugates and their use in the treatment of cancer, an autoimmune disease or an infectious disease
AT03772186T ATE516818T1 (en) 2002-07-31 2003-07-31 AURISTATIN CONJUGATES AND THEIR USE IN THE TREATMENT OF CANCER, AN AUTOIMMUNE DISEASE OR AN INFECTIOUS DISEASE
US10/522,911 US7659241B2 (en) 2002-07-31 2003-07-31 Drug conjugates and their use for treating cancer, an autoimmune disease or an infectious disease
AU2003263964A AU2003263964C1 (en) 2002-07-31 2003-07-31 Drug conjugates and their use for treating cancer, an autoimmune disease or an infectious disease
CA2494105A CA2494105C (en) 2002-07-31 2003-07-31 Drug conjugates and their use for treating cancer, an autoimmune disease or an infectious disease
SI200332051T SI1545613T1 (en) 2002-07-31 2003-07-31 Auristatin conjugates and their use for treating cancer, an autoimmune disease or an infectious disease
EP03772186A EP1545613B9 (en) 2002-07-31 2003-07-31 Auristatin conjugates and their use for treating cancer, an autoimmune disease or an infectious disease
JP2004524294A JP4741838B2 (en) 2002-07-31 2003-07-31 Drug conjugates and their use for treating cancer, autoimmune diseases or infectious diseases
US12/408,646 US7829531B2 (en) 2002-07-31 2009-03-20 Drug conjugates and their use for treating cancer, an autoimmune disease or an infectious disease
US12/621,406 US7851437B2 (en) 2002-07-31 2009-11-18 Drug conjugates and their use for treating cancer, an autoimmune disease or an infectious disease
AU2010201459A AU2010201459B2 (en) 2002-07-31 2010-04-13 Drug conjugates and their use for treating cancer, an autoimmune disease or an infectious disease
US12/880,028 US8906376B2 (en) 2002-07-31 2010-09-10 Drug conjugates and their use for treating cancer, an autoimmune disease or an infectious disease
BE2012C047C BE2012C047I2 (en) 2002-07-31 2012-10-31
FR12C0066C FR12C0066I2 (en) 2002-07-31 2012-10-31 AURISTATIN CONJUGATES AND THEIR USE IN THE TREATMENT OF CANCER, AN AUTOIMMUNE DISEASE OR AN INFECTIOUS DISEASE
CY2013004C CY2013004I2 (en) 2002-07-31 2013-01-10 AURISTATIN CONJUGATION PRODUCTS AND THEIR USE FOR THE TREATMENT OF CANCER, AUTOIMMUNE DISEASE OR INFECTIOUS DISEASE
HUS1300002C HUS1300002I1 (en) 2002-07-31 2013-01-18 Auristatin conjugates and their use for treating cancer, an autoimmune disease or an infectious disease

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US40040302P 2002-07-31 2002-07-31
US60/400,403 2002-07-31

Related Child Applications (3)

Application Number Title Priority Date Filing Date
US10522911 A-371-Of-International 2003-07-31
US12/408,646 Continuation US7829531B2 (en) 2002-07-31 2009-03-20 Drug conjugates and their use for treating cancer, an autoimmune disease or an infectious disease
US12/621,406 Continuation US7851437B2 (en) 2002-07-31 2009-11-18 Drug conjugates and their use for treating cancer, an autoimmune disease or an infectious disease

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WO2004010957A2 WO2004010957A2 (en) 2004-02-05
WO2004010957A3 WO2004010957A3 (en) 2004-06-10
WO2004010957B1 true WO2004010957B1 (en) 2004-08-19

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US (5) US7659241B2 (en)
EP (3) EP2353611B1 (en)
JP (1) JP4741838B2 (en)
AT (1) ATE516818T1 (en)
AU (2) AU2003263964C1 (en)
BE (1) BE2012C047I2 (en)
CA (2) CA2802205C (en)
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