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US 12,215,080 B2Granted
Hydrazinyl-pyrrolo compounds and methods for producing a conjugate
AssigneeRedwood Bioscience, Inc.
InventorsDavid Rabuka, Aaron Edward Albers, Romas Alvydas Kudirka, Albert W. Garofalo, Jesse M. McFarland
Life of this patent
Estimating the term…
Abstract
The present disclosure provides conjugate structures and hydrazinyl-pyrrolo compound structures used to produce these conjugates. The disclosure also encompasses methods of production of such conjugates, as well as methods of using the same.
Claims21
A conjugate of formula (IIIa):
- wherein:
- m is 0 or 1;
- R1 is selected from hydrogen and alkyl;
- R2 and R3 are each alkyl;
- X1 is C or N, wherein if X1 is N, then Y1 is absent;
- X2, X3 and X4 are each C;
- Y1, if present, Y2, Y3 and Y4 are each hydrogen;
- L is a linker represented by -(T1-V1)a-(T2-V2)b-(T3-V3)c-(T4-V4)d-(T5-V5)e-, wherein a, b and c are each 1, and d and e are each independently 0 or 1, where the sum of a, b, c, d and e is 3 to 5;
- wherein T1, T2, T3, T4 and T5 and V1, V2, V3, V4 and V5 are selected from the following table:
- T1
- V1
- T2
- V2
- T3
- (C1-C12)alkylene
- —CO—
- (AA)p
- —NR11—
- (PEG)n
- (C1-C12)alkylene
- —CO—
- (AA)p
- —NR11—
- (PEG)n
- (C1-C12)alkylene
- —CONR11—
- (PEG)n
- —CO—
- (EDA)w
- (C1-C12)alkylene
- —CO—
- (EDA)w
- —CO—
- (CR13OH)h
- (C1-C12)alkylene
- —CO—
- (AA)p
- —NR11—
- (C1-C12)
- alkylene
- (C1-C12)alkylene
- —CONR11—
- (PEG)n
- —CO—
- (AA)p
- (C1-C12)alkylene
- —CONR11—
- (PEG)n
- —CO—
- (AA)p
- (C1-C12)alkylene
- —CONR11—
- (PEG)n
- —CO—
- (AA)p
- (C1-C12)alkylene
- —CONR11—
- (PEG)n
- —CO—
- (AA)p
- (C1-C12)alkylene
- —CO—
- (EDA)w
- —CO—
- (CR13OH)h
- (C1-C12)alkylene
- —CO—
- (AA)p
- —NR11—
- (C1-C12)
- alkylene
- (C1-C12)alkylene
- —CO—
- (AA)p
- —NR11—
- (PEG)n
- (C1-C12)alkylene
- —CO—
- (AA)p
- —NR11—
- (C1-C12)
- alkylene
- (C1-C12)alkylene
- —CO—
- (AA)p
- —NR11—
- (PEG)n
- (C1-C12)alkylene
- —CO—
- (AA)p
- —NR11—
- (PEG)n
- (C1-C12)alkylene
- —CO—
- (AA)p
- —NR11—
- (PEG)n
- (C1-C12)alkylene
- —CO—
- (AA)p
- —NR11—
- (PEG)n
- (C1-C12)alkylene
- —CO—
- (AA)p
- —NR11—
- (PEG)n
- (C1-C12)alkylene
- —CONR11—
- (PEG)n
- —CO—
- (AA)p
- (C1-C12)alkylene
- —CONR11—
- (PEG)n
- —CO—
- (AA)p
- (C1-C12)alkylene
- —CO—
- (EDA)w
- —CO—
- (CR13OH)h
- (C1-C12)alkylene
- —CO—
- (AA)p
- —NR11—
- (PEG)n
- (C1-C12)alkylene
- —CO—
- (AA)p
- —NR11—
- (PEG)n
- (C1-C12)alkylene
- —CONR11—
- (PEG)n
- —CO—
- MABO
- (C1-C12)alkylene
- —CO—
- (AA)p
- —NR11—
- (PEG)n
- (C1-C12)alkylene
- —CO—
- (AA)p
- —NR11—
- (PEG)n
- (C1-C12)alkylene
- —CO—
- (AA)p
- —NR11—
- (PEG)n
- (C1-C12)alkylene
- —CONR11—
- (PEG)n
- —CO—
- MABC
- (C1-C12)alkylene
- —CONR11—
- substituted
- —NR11—
- (PEG)n
- (C1-C12)
- alkylene
- (C1-C12)alkylene
- —CONR11—
- (PEG)n
- —CO—
- (AA)p
- (C1-C12)alkylene
- —CONR11—
- (C1-C12)
- —
- (CR13OH)h
- alkylene
- (C1-C12)alkylene
- —CO—
- P4A
- —CO—
- (C1-C12)
- alkylene
- (C1-C12)alkylene
- —CO—
- P4A
- —CO—
- (C1-C12)
- alkylene
- (C1-C12)alkylene
- —CO—
- P4A
- —CO—
- (C1-C12)
- alkylene
- (C1-C12)alkylene
- —CO—
- P4A
- —CO—
- (C1-C12)
- alkylene
- V3
- T4
- V4
- T5
- V5
- —CO—
- —
- —
- —
- —
- —NR11—
- —
- —
- —
- —
- —
- —
- —
- —
- —
- —CONR11—
- (C1-C12)alkylene
- —CO—
- —
- —
- —CO—
- —
- —
- —
- —
- —
- —
- —
- —
- —
- —
- MABO
- —
- —
- —
- —
- PABO
- —
- —
- —
- —
- PABC
- —
- —
- —
- —CO—
- (AA)p
- —
- —
- —
- —CO—
- (AA)p
- —
- —
- —
- —CO—
- (AA)p
- —
- —
- —
- —CO—
- (AA)p
- —
- —
- —
- —CO—
- (AA)p—
- —
- —
- —
- PABC—
- (AA)p
- —CO—
- (AA)p—
- —
- PABC—
- —
- (AA)p
- —CO—
- (AA)p—
- —
- —
- —
- PABO
- —CO—
- (AA)p
- —
- PABO
- —
- —SO2—
- (AA)p
- —
- —
- —
- —
- PABC—
- —
- —
- —
- (AA)p
- —
- PABC
- —
- —
- —
- —CONR11—
- (PEG)n
- —CO—
- —
- —
- —CO—
- MABC—
- —
- —
- —
- (AA)p—
- —CO—
- MABC
- —
- (AA)p
- —
- —
- —
- —
- —
- —
- —CO—
- MABO
- —
- —
- —
- —CO—
- PABO
- —
- —
- —
- —CO—
- PABC
- —
- —
- —
- —
- (AA)p
- —
- —
- —
- —CO—
- —
- —
- —
- —
- —
- PABC
- —
- —NR11—
- —
- —CONR11—
- —
- —
- —
- —
- —CO—
- (AA)p
- —
- PABO
- —CO—
- —CO—
- (AA)p
- —
- PABO
- —
- —CO—
- (AA)p
- —
- PABC
- —
- (AA)p
- —CO—
- (AA)p—
- —
- —
- —
- wherein:
- EDA is an ethylene diamine moiety, PEG is a polyethylene glycol, and AA is an amino acid residue;
- piperidin-4-amino (P4A) is
- MABC is
- MABO is
- PABC is
- PABO is
- w is an integer from 1 to 20;
- n is an integer from 1 to 30;
- p is an integer from 1 to 20;
- h is an integer from 1 to 12;
- R11 is selected from hydrogen, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, alkoxy, substituted alkoxy, amino, substituted amino, carboxyl, carboxyl ester, acyl, acyloxy, acyl amino, amino acyl, alkylamide, substituted alkylamide, sulfonyl, thioalkoxy, substituted thioalkoxy, aryl, substituted aryl, heteroaryl, substituted heteroaryl, cycloalkyl, substituted cycloalkyl, heterocyclyl, and substituted heterocyclyl;
- R13 is selected from hydrogen, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, alkoxy, substituted alkoxy, amino, substituted amino, carboxyl, carboxyl ester, acyl, acyloxy, acyl amino, amino acyl, alkylamide, substituted alkylamide, sulfonyl, thioalkoxy, substituted thioalkoxy, aryl, substituted aryl, heteroaryl, substituted heteroaryl, cycloalkyl, substituted cycloalkyl, heterocyclyl, and substituted heterocyclyl;
- each R14 is independently selected from hydrogen, alkyl, substituted alkyl, a polyethylene glycol moiety, aryl, and substituted aryl;
- each R15 is independently selected from hydrogen, halogen, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, alkoxy, substituted alkoxy, amino, substituted amino, carboxyl, carboxyl ester, acyl, acyloxy, acyl amino, amino acyl, alkylamide, substituted alkylamide, sulfonyl, thioalkoxy, substituted thioalkoxy, aryl, substituted aryl, heteroaryl, substituted heteroaryl, cycloalkyl, substituted cycloalkyl, heterocyclyl, and substituted heterocyclyl;
- each R16 is independently selected from hydrogen, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, alkoxy, substituted alkoxy, amino, substituted amino, carboxyl, carboxyl ester, acyl, acyloxy, acyl amino, amino acyl, alkylamide, substituted alkylamide, sulfonyl, thioalkoxy, substituted thioalkoxy, aryl, substituted aryl, heteroaryl, substituted heteroaryl, cycloalkyl, substituted cycloalkyl, heterocyclyl, and substituted heterocyclyl;
- W1 is a drug;
- and
- W2 is an antibody.
402 more elements
Dependencies are inferred from the claim text.