# US 10,370,399 B2 · Calicheamicin-antibody-drug conjugates and methods of use

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- Number: US 10,370,399 B2
- Document ID: US10370399B2
- Status: Granted
- Kind: B2
- Application number: 15/297,384
- Filed: 2016-10-19
- Published: 2017-04-20
- Granted: 2019-08-06
- Earliest claimed: 2015-10-20
- Assignees: Genentech, Inc.
- Applicants: Genentech, Inc.
- Inventors: Thomas Pillow
- Web page: https://patentgrep.com/patent/US10370399B2

## CPC

- C07H 15/207: Cyclohexane rings not substituted by nitrogen atoms, e.g. kasugamycins
- A61K 39/39558: {against tumor tissues, cells, antigens}
- A61K 47/545: {Heterocyclic compounds (A61K47/558 takes precedence)}
- A61K 47/6807: {the drug or compound being a sugar, nucleoside, nucleotide, nucleic acid, e.g. RNA antisense}
- A61K 47/6809: {Antibiotics, e.g. antitumor antibiotics anthracyclins, adriamycin, doxorubicin or daunomycin}
- A61P 35/00: Antineoplastic agents
- C07H: SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS (derivatives of aldonic or saccharic acids C07C, C07D; aldonic acids, saccharic acids C07C59/105, C07C59/285; cyanohydrins C07C255/16; glycals C07D; compounds of unknown constitution C07G; polysaccharides, derivatives thereof C08B; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification C12N15/00; sugar industry C13)
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

The invention relates generally to a calicheamicin molecule activated with a leaving group. The invention further relates generally to an antibody-drug conjugate comprising an antibody directly conjugated by a disulfide to one or more calicheamicin molecules.

## Claims

### Claim 1

A compound of Formula I:
wherein R is selected from H, —C(O)R′, —C(O)NR1R2, —S(O)2R1, and —S(O)2NR2R1; R1 and R2 are independently selected from C1-C6 alkyl and C6-C20 aryl; R3 is selected from NO2, Cl, F, CN, CO2H; and Br, and q is 0, 1, or 2.

### Claim 2 (depends on 1)

The compound of claim 1 wherein R is —C(O)CH3.

### Claim 3 (depends on 1, 2)

The compound of claim 1 or claim 2 wherein R3 is NO2 and q is 1.

### Claim 4 (depends on 3)

The compound of claim 3 having Formula Ia:

### Claim 5

A compound of Formula II:
wherein R is selected from H, —C(O)R′, —C(O)NR1R2, —S(O)2R1, and —S(O)2NR2R1; and R1 and R2 are independently selected from C1-C6 alkyl and C6-C20 aryl.

### Claim 6 (depends on 5)

The compound of claim 5 having Formula IIa: