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US 2003/0083263 A1Published application
Pentapeptide compounds and uses related thereto
OwnerSvetlana Doronina, Brian Toki +1inventors
InventorsSvetlana Doronina, Brian Toki, Peter Senter
Life of this patent
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Abstract
Pentapeptide compounds are disclosed. The compounds have biological activity, e.g., cytotoxicity, and/or include a reactive linker that can serve as a reaction site for joining to a targeting agent, e.g., an antibody.
Claims75
A compound of the formula
- 84
- wherein, independently at each location:
- R1 is selected from hydrogen and lower alkyl;
- R2 is selected from hydrogen and lower alkyl;
- R3 is lower alkyl;
- R4 is selected from lower alkyl, aryl, and —CH2—C5-7carbocycle when R5 is selected from H and methyl, or R4 and R5 together form a carbocycle of the partial formula —(CRaRb)n— wherein Ra and Rb are independently selected from hydrogen and lower alkyl and n is selected from2,3,4,5 and6;
- R6 is selected from hydrogen and lower alkyl;
- R7 is sec-butyl or iso-butyl;
- R8 is selected from hydrogen and lower alkyl;
- and
- R9 is selected from
- 85
- R11 is selected from hydrogen and lower alkyl;
- R12 is selected from lower alkyl, halogen, and methoxy, and m is 0-5 where R12 is independently selected at each occurrence;
- and
- 86
- wherein:
- R14 is selected from a direct bond, divalent lower alkyl and divalent aryl;
- R15 is selected from hydrogen, lower alkyl and aryl;
- R16 is selected from divalent lower alkyl, divalent aryl, and —(CH2OCH2)pCH2— where p is 1-5;
- and
- R17 is selected from
- 87
- where Y═O or S.
21 more elements
A compound of the formula
- 101
- wherein, independently at each location:
- R2 is selected from hydrogen and lower alkyl;
- R3 is lower alkyl;
- R4 is selected from lower alkyl, aryl, and —CH2—C5-7carbocycle when R5 is selected from H and methyl, or R4 and R5 together form a carbocycle of the partial formula —(CRaRb)n— wherein Ra and Rb are independently selected from hydrogen and lower alkyl and n is selected from 2, 3, 4, 5 and 6;
- R6 is selected from hydrogen and lower alkyl;
- R7 is sec-butyl or iso-butyl;
- R8 is selected from hydrogen and lower alkyl;
- R11 is selected from hydrogen and lower alkyl;
- R12 is selected from lower alkyl, halogen, and methoxy, and m is 0-5 where R12 is independently selected at each occurrence;
- and
- R20 is a reactive linker group having a reactive site that allows R20 to be reacted with a targeting moiety, where R20 can be bonded to the carbon labeled “x” by either a single or double bond.
9 more elements
A compound of the formula
- 110
- wherein, independently at each location:
- R1 is selected from hydrogen and lower alkyl;
- R2 is selected from hydrogen and lower alkyl;
- R3 is lower alkyl;
- R4 is selected from lower alkyl, aryl, and —CH2—C5-7carbocycle when R5 is selected from H and methyl, or R4 and R5 together form a carbocycle of the partial formula —(CRaRb)n— wherein Ra and Rb are independently selected from hydrogen and lower alkyl and n is selected from 2, 3, 4, 5 and 6;
- R6 is selected from hydrogen and lower alkyl;
- R7 is sec-butyl or iso-butyl;
- R8 is selected from hydrogen and lower alkyl;
- R11 is selected from hydrogen and lower alkyl;
- R12 is selected from lower alkyl, halogen, and methoxy, and m is 0-5 where R12 is independently selected at each occurrence;
- and
- R20 is a reactive linker group having a reactive site that allows R20 to be reacted with a targeting moiety, where R20 can be bonded to the carbon labeled “x” by either a single or double bond.
10 more elements
A compound of the formula
- 115
- wherein, independently at each location:
- R1 is selected from hydrogen and lower alkyl;
- R2 is selected from hydrogen and lower alkyl;
- R3 is lower alkyl;
- R4 is selected from lower alkyl, aryl, and —CH2—C5-7carbocycle when R5 is selected from H and methyl, or R4 and R5 together form a carbocycle of the partial formula —(CRaRb)n— wherein Ra and Rb are independently selected from hydrogen and lower alkyl and n is selected from 2, 3, 4, 5 and 6;
- R6 is selected from hydrogen and lower alkyl;
- R7 is sec-butyl or iso-butyl;
- R8 is selected from hydrogen and lower alkyl;
- and
- R20 is a reactive linker group comprising a reactive site that allows R20 to be reacted with a targeting moiety.
8 more elements
A compound of the formula
- 120
A compound of the formula
- 121
- wherein, independently at each location:
- R1 is selected from hydrogen and lower alkyl;
- R2 is selected from hydrogen and lower alkyl;
- R3 is lower alkyl;
- R4 is selected from lower alkyl, aryl, and —CH2—C5-7carbocycle when R5 is selected from H and methyl, or R4 and R5 together form a carbocycle of the partial formula —(CRaRb)n— wherein Ra and Rb are independently selected from hydrogen and lower alkyl and n is selected from 2, 3, 4, 5 and 6;
- R6 is selected from hydrogen and lower alkyl;
- R7 is sec-butyl or iso-butyl;
- R8 is selected from hydrogen and lower alkyl;
- R11 is selected from hydrogen and lower alkyl;
- and
- R18 is selected from hydrogen, a hydroxyl protecting group, and a direct bond where OR18 represents ═O.
9 more elements
A compound of the formula
- 123
- wherein, independently at each location:
- R1 is selected from hydrogen and lower alkyl;
- R2 is selected from hydrogen and lower alkyl;
- R3 is lower alkyl;
- R4 is selected from lower alkyl, aryl, and —CH2—C5-7carbocycle when R5 is selected from H and methyl, or R4 and R5 together form a carbocycle of the partial formula —(CRaRb)n— wherein Ra and Rb are independently selected from hydrogen and lower alkyl and n is selected from 2, 3, 4, 5 and 6;
- R6 is selected from hydrogen and lower alkyl;
- R7 is sec-butyl or iso-butyl;
- R8 is selected from hydrogen and lower alkyl;
- and
- R19 is selected from hydroxy- and oxo-substituted lower alkyl.
8 more elements
Dependencies are inferred from the claim text.