# US 11,999,758 B2 · Inhibitors of the YAP/TAZ-TEAD interaction and their use in the treatment of cancer

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 11,999,758 B2
- Document ID: US11999758B2
- Status: Granted
- Kind: B2
- Application number: 17/278,429
- Filed: 2019-10-02
- Published: 2021-10-21
- Granted: 2024-06-04
- Earliest claimed: 2018-10-02
- Assignees: Inventiva
- Applicants: Inventiva
- Inventors: Martine Barth; Sylvie Contal; Jean-Louis Junien; Christine Massardier; Christian Montalbetti; Anne Soude
- Web page: https://patentgrep.com/patent/US11999758B2

## CPC

- C07D 275/06: with hetero atoms directly attached to the ring sulfur atom
- C07F 5/025: {Boronic and borinic acid compounds}
- A61P 35/00: Antineoplastic agents
- C07D 239/94: Nitrogen atoms
- C07D 403/04: directly linked by a ring-member-to-ring-member bond
- C07D 417/04: directly linked by a ring-member-to-ring-member bond
- C07D 487/04: Ortho-condensed systems
- C07D 491/048: the oxygen-containing ring being five-membered
- C07D 495/04: Ortho-condensed systems
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

The invention relates to compounds of formula (I): wherein R1, R2, R3, R4, R5 and are as defined in the description.

## Claims

### Claim 1

A compound of formula (I):
wherein:
is a substituted or unsubstituted N-containing monocyclic, bicyclic or tricyclic heteroraryl;
R1 is H, an alkyl optionally substituted with one or two groups R6 or an aryl optionally substituted with one or more groups R6;
R2 is H or alkyl; or
R1 and R2 are bound together to form a 5- or 6-membered heterocycle;
R3 and R4 are each independently H or an alkyl optionally substituted with one or two groups R6; or
R3 and R4 are bound together to form a 5- to 8-membered heterocycle;
R5 is H, a halogen, an alkyl optionally substituted with 1 or 2 groups R6, or an alkoxy optionally substituted with 1 or 2 groups R6; or
R4 and R5 are bound together to form a 5- to 7-membered heterocyle;
R6 is hydroxy, alkoxy, —NR15R16, —CO—Y—R17, —CN, —CF3, or aryl;
R15 and R16 are each independently H, alkyl, —CO-alkyl or form together with the nitrogen atom a 3- to 6-membered cyclic group;
Y is —O— or —NR18—;
R17 is H or alkyl; and
R18 is H, alkyl or hydroxyalkyl;
provided that when R3 is H and R4 and R5 are bound together to form a 5-membered heterocycle, then R1 is not H;
or a pharmaceutically acceptable salt thereof.

### Claim 2 (depends on 1)

The compound of claim 1, or a pharmaceutically acceptable salt thereof, wherein:
is selected from the groups of formulae (II), (III), (IV), (V), (VI), (VII), (VIII), (IX), (X), (XI), (XII), (XIII), (XIV), (XV), (XVI), (XVII) and (XVIII):
wherein:
R7, R8, R9 and R10 are each independently H, a halogen, an alkyl optionally substituted with 1 or 2 groups R6, a perfluoroalkyl, an alkoxy optionally substituted with 1 or 2 groups R6, or a cyano group;
R10 can also represent a cycloalkyl, an aryl, —NR15R16, or —CO—Y—R22 where R22 is H, alkyl optionally substituted with hydroxy or alkoxy, or —NR15R16;
R10 can also be bound together with R12 to form a 6-membered carbocycle;
R11, R12, and R13 are each independently H, an alkyl optionally substituted with 1 or 2 groups R6, or a perfluoroalkyl;
R12 can also represent an alkylthio or a group —NR15R16;
R13 can also represent a cycloalkyl optionally substituted with hydroxyl or alkoxyalkyl.

### Claim 3 (depends on 1)

The compound of claim 1, or a pharmaceutically acceptable salt thereof, wherein R1 is an alkyl optionally substituted with one or two groups R6 or an aryl optionally substituted with one or more groups R6 and R6 is hydroxy, alkoxy, —NR15R16, —CO—Y—R17, —CN, —CF3, or aryl.

### Claim 4 (depends on 1)

The compound of claim 1, or a pharmaceutically acceptable salt thereof, wherein:
R3 and R4 are each independently H or an alkyl; or
R3 and R4 are bound together to form a 5- to 8-membered heterocycle;
R5 is H, a halogen, an alkyl optionally substituted with 1 or 2 groups R6, or an alkoxy optionally substituted with 1 or 2 groups R6 and R6 is hydroxy, alkoxy, —NR15R16, —CO—Y—R17, —CN, —CF3, or aryl.

### Claim 5 (depends on 4)

The compound of claim 4, which is selected from:
[4-[(E)-[(1,1-dioxo-1,2-benzothiazol-3-yl)-isobutyl-hydrazono]methyl]-2-methoxy-phenyl]boronic acid;
[4-[(E)-[isobutyl-(5-methoxy-1,1-dioxo-1,2-benzothiazol-3-yl)hydrazono]methyl]-2-methoxy-phenyl]boronic acid;
[4-[(E)-[(5,7-dimethoxy-1,1-dioxo-1,2-benzothiazol-3-yl)-isobutyl-hydrazono]methyl]-2-methoxy-phenyl]boronic acid;
[4-[(E)-[(1,1-dioxo-1,2-benzothiazol-3-yl)-ethyl-hydrazono]methyl]-2-methoxy-phenyl]boronic acid;
[4-[(E)-[(1,1-dioxo-1,2-benzothiazol-3-yl)-(2-methoxyethyl)hydrazono]methyl]-2-methoxy-phenyl]boronic acid;
[2-chloro-4-[(E)-[(1,1-dioxo-1,2-benzothiazol-3-yl)-isobutyl-hydrazono]methyl]phenyl]boronic acid;
[4-[(E)-[isobutyl-(5-methyl-1,1-dioxo-1,2-benzothiazol-3-yl)hydrazono]methyl]-2-methoxy-phenyl]boronic acid;
[4-[(E)-[(1,1-dioxo-1,2-benzothiazol-3-yl)-isobutyl-hydrazono]methyl]phenyl]boronic acid;
[4-[(E)-[isobutyl-[5-(2-methoxyethoxy)-1,1-dioxo-1,2-benzothiazol-3-yl]hydrazono]methyl]-2-methoxy-phenyl]boronic acid;
[4-[(E)-[(6-cyano-1,1-dioxo-1,2-benzothiazol-3-yl)-isobutyl-hydrazono]methyl]-2-methoxy-phenyl]boronic acid;
[4-[(E)-[(1,1-dioxo-1,2-benzothiazol-3-yl)-isobutyl-hydrazono]methyl]-2-(2-methoxyethoxy)phenyl]boronic acid;
[4-[(E)-[[5-(3-hydroxypropoxy)-1,1-dioxo-1,2-benzothiazol-3-yl]-isobutyl-hydrazono]methyl]-2-methoxy-phenyl]boronic acid;
[4-[(E)-[isobutyl-(8-methoxyquinazolin-4-yl)hydrazono]methyl]-2-methoxy-phenyl]boronic acid;
[4-[(E)-[(1,1-dioxo-1,2-benzothiazol-3-yl)-isobutyl-hydrazono]methyl]-2-ethoxy-phenyl]boronic acid;
[2-chloro-4-[(E)-[(5,7-dimethoxy-1,1-dioxo-1,2-benzothiazol-3-yl)-isobutyl-hydrazono]methyl]phenyl]boronic acid;
[4-[(E)-[(1,1-dioxo-1,2-benzothiazol-3-yl)-sec-butyl-hydrazono]methyl]-2-methoxy-phenyl]boronic acid;
[4-[(E)-[(6,8-dimethoxyquinazolin-4-yl)-isobutyl-hydrazono]methyl]-2-methoxy-phenyl]boronic acid;
[4-[(E)-[(7-fluoroquinazolin-4-yl)-isobutyl-hydrazono]methyl]-2-methoxy-phenyl]boronic acid;
[4-[(E)-[isobutyl-(6-methoxyquinazolin-4-yl)hydrazono]methyl]-2-methoxy-phenyl]boronic acid;
[4-[(E)-[isobutyl(thieno[3,2-d]pyrimidin-4-yl)hydrazono]methyl]-2-methoxy-phenyl]boronic acid;
[4-[(E)-[ethyl-(8-methoxyquinazolin-4-yl)hydrazono]methyl]-2-methoxy-phenyl]boronic acid;
[2-methoxy-4-[(E)-[(8-methoxyquinazolin-4-yl)-methyl-hydrazono]methyl]phenyl]-boronic acid;
[4-[2-(1,1-dioxo-1,2-benzothiazol-3-yl)-3-methyl-4,5-dihydro-3H-pyridazin-6-yl]-2-methoxy-phenyl]boronic acid;
[4-[2-(5,7-dimethoxy-1,1-dioxo-1,2-benzothiazol-3-yl)-3-methyl-4,5-dihydro-3H-pyridazin-6-yl]-2-methoxy-phenyl]boronic acid;
[2-methoxy-4-[2-(8-methoxyquinazolin-4-yl)-3-methyl-4,5-dihydro-3H-pyridazin-6-yl]phenyl]boronic acid;
[4-[2-(1,1-dioxo-1,2-benzothiazol-3-yl)-4,4-dimethyl-3,5-dihydropyridazin-6-yl]-2-methoxy-phenyl]boronic acid;
[4-[4-(1,1-dioxo-1,2-benzothiazol-3-yl)-6-methyl-5,6-dihydro-1,3,4-oxadiazin-2-yl]-2-methoxy-phenyl]boronic acid;
[2-methoxy-4-[(E)-[methyl-(5-methylpyridazin-3-yl)hydrazono]methyl]phenyl]boronic acid;
2-[4-[(E)-[(1,1-dioxo-1,2-benzothiazol-3-yl)-isobutyl-hydrazono]methyl]-2-methoxy-phenyl]-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione;
[4-[(E)-[ethyl-(7-methylthieno[3,2-d]pyrimidin-4-yl)hydrazono]methyl]-2-methoxy-phenyl]boronic acid;
[4-[(E)-[ethyl(thieno[3,2-d]pyrimidin-4-yl)hydrazono]methyl]-2-methoxy-phenyl]boronic acid;
[4-[(E)-[ethyl(thiazolo[4,5-d]pyrimidin-7-yl)hydrazono]methyl]-2-methoxy-phenyl]boronic acid;
[4-[(E)-[ethyl(furo[2,3-d]pyrimidin-4-yl)hydrazono]methyl]-2-methoxy-phenyl]boronic acid;
[4-[(E)-[ethyl-(7-methylpyrrolo[2,3-d]pyrimidin-4-yl)hydrazono]methyl]-2-methoxy-phenyl]boronic acid;
[4-[(E)-[isobutyl-(7-methylthieno[3,2-d]pyrimidin-4-yl)hydrazono]methyl]-2-methoxy-phenyl]boronic acid;
[4-[(E)-[isobutyl-(2-methylthieno[3,2-d]pyrimidin-4-yl)hydrazono]methyl]-2-methoxy-phenyl]boronic acid;
[4-[(E)-[isobutyl-(6-methylthieno[3,2-d]pyrimidin-4-yl)hydrazono]methyl]-2-methoxy-phenyl]boronic acid;
[2-methoxy-4-[(E)-[2-methoxyethyl(thieno[3,2-d]pyrimidin-4-yl)hydrazono]methyl]-phenyl]boronic acid;
[2-methoxy-4-[(E)-[methyl-(7-methylthieno[3,2-d]pyrimidin-4-yl)hydrazono]methyl]-phenyl]boronic acid;
[2-methoxy-4-(3-methyl-2-thieno[3,2-d]pyrimidin-4-yl-4,5-dihydro-3H-pyridazin-6-yl)phenyl]boronic acid;
[2-methoxy-4-[3-methyl-2-(7-methylpyrrolo[2,3-d]pyrimidin-4-yl)-4,5-dihydro-3H-pyridazin-6-yl]phenyl]boronic acid;
[4-[4-(7-fluoroquinazolin-4-yl)-6-methyl-5,6-dihydro-1,3,4-oxadiazin-2-yl]-2-methoxy-phenyl]boronic acid, and
pharmaceutically acceptable salts thereof.

### Claim 6 (depends on 1)

The compound of claim 1, or a pharmaceutically acceptable salt thereof, wherein:
R3 is H or an alkyl optionally substituted with one or two groups R6;
R4 and R5 are bound together to form a 5- to 7-membered heterocycle;
R6 is hydroxy, alkoxy, —NR15R16, —CO—Y—R17, —CN, —CF3, or aryl.

### Claim 7 (depends on 1)

The compound of claim 1, or a pharmaceutically acceptable salt thereof, represented by formula (Ib):
wherein:
R1 is H, an alkyl optionally substituted with one or two groups R6 or an aryl optionally substituted with one or more groups R6;
R2 is H or alkyl;
R3 is H or an alkyl optionally substituted with one or two groups R6;
each R14 is independently H, an alkyl optionally substituted with one or two groups R6, an aryl, —NR15R16, or —CO—Y—R17;
R6 is hydroxy, alkoxy, —NR15R16, —CO—Y—R17, —CN, —CF3, or aryl;
R15 and R16 are each independently H, alkyl, —CO-alkyl or form together with the nitrogen atom a 3- to 6-membered cyclic group;
Y is —O— or —NR18—;
R17 is H or alky;
R18 is H, alkyl or hydroxyalkyl;
n is 1, 2 or 3; and
is a substituted or unsubstituted N-containing monocyclic, bicyclic or tricyclic heteroraryl.

### Claim 8 (depends on 6)

The compound of claim 6, which is selected from:
N-[(E)-(1-hydroxy-3H-2,1-benzoxaborol-5-yl)methyleneamino]-N-isobutyl-1,1-dioxo-1,2-benzothiazol-3-amine;
N-[(E)-(1-hydroxy-3H-2,1-benzoxaborol-5-yl)methyleneamino]-N-(2-methoxyethyl)-1,1-dioxo-1,2-benzothiazol-3-amine;
N-[(E)-(1-hydroxy-3H-2,1-benzoxaborol-5-yl)methyleneamino]-N-(3-methoxypropyl)-1,1-dioxo-1,2-benzothiazol-3-amine;
N-[(E)-(1-hydroxy-3H-2,1-benzoxaborol-5-yl)methyleneamino]-N-methyl-1,1-dioxo-1,2-benzothiazol-3-amine;
N-ethyl-N-[(E)-(1-hydroxy-3H-2,1-benzoxaborol-5-yl)methyleneamino]-1,1-dioxo-1,2-benzothiazol-3-amine;
5-fluoro-N-[(E)-(1-hydroxy-3H-2,1-benzoxaborol-5-yl)methyleneamino]-N-isobutyl-1,1-dioxo-1,2-benzothiazol-3-amine;
N-[(E)-(1-hydroxy-3H-2,1-benzoxaborol-5-yl)methyleneamino]-N-isobutyl-5-methyl-1,1-dioxo-1,2-benzothiazol-3-amine;
N-[(E)-(1-hydroxy-3H-2,1-benzoxaborol-5-yl)methyleneamino]-N-isobutyl-6-methoxy-1,1-dioxo-1,2-benzothiazol-3-amine;
N-[(E)-(1-hydroxy-3H-2,1-benzoxaborol-5-yl)methyleneamino]-N-isobutyl-6-methyl-1,1-dioxo-1,2-benzothiazol-3-amine;
N-[(E)-(1-hydroxy-3H-2,1-benzoxaborol-5-yl)methyleneamino]-N-isobutyl-8-methoxy-quinazolin-4-amine;
N-[(E)-(1-hydroxy-3H-2,1-benzoxaborol-5-yl)methyleneamino]-8-methoxy-N-methyl-quinazolin-4-amine;
N-ethyl-N-[(E)-(1-hydroxy-3H-2,1-benzoxaborol-5-yl)methyleneamino]-8-methoxy-quinazolin-4-amine;
N-[(E)-(1-hydroxy-3H-2,1-benzoxaborol-5-yl)methyleneamino]-N-isobutyl-thieno[3,2-d]pyrimidin-4-amine;
N-[(E)-(1-hydroxy-3H-2,1-benzoxaborol-5-yl)methyleneamino]-N,5-dimethyl-1,1-dioxo-1,2-benzothiazol-3-amine;
N-[(E)-(1-hydroxy-3H-2,1-benzoxaborol-5-yl)methyleneamino]-5-methoxy-N-methyl-1,1-dioxo-1,2-benzothiazol-3-amine;
N-ethyl-N-[(E)-(1-hydroxy-3H-2,1-benzoxaborol-5-yl)methyleneamino]thieno[3,2-d]pyrimidin-4-amine;
N-ethyl-N-[(E)-(1-hydroxy-3H-2,1-benzoxaborol-5-yl)methyleneamino]-7H-pyrrolo[2,3-d]pyrimidin-4-amine;
N-ethyl-N-[(E)-(1-hydroxy-3H-2,1-benzoxaborol-5-yl)methyleneamino]thieno[2,3-d]pyrimidin-4-amine;
N-ethyl-N-[(E)-(1-hydroxy-3H-2,1-benzoxaborol-5-yl)methyleneamino]-1-methyl-pyrazolo[3,4-d]pyrimidin-4-amine;
N-ethyl-N-[(E)-(1-hydroxy-3H-2,1-benzoxaborol-5-yl)methyleneamino]-7-methyl-thieno[3,2-d]pyrimidin-4-amine;
N-ethyl-N-[(E)-(1-hydroxy-3H-2,1-benzoxaborol-5-yl)methyleneamino]furo[2,3-d]pyrimidin-4-amine;
N-ethyl-N-[(E)-(1-hydroxy-3H-2,1-benzoxaborol-5-yl)methyleneamino]-7-methyl-pyrrolo[2,3-d]pyrimidin-4-amine;
N-ethyl-N-[(E)-(1-hydroxy-3H-2,1-benzoxaborol-5-yl)methyleneamino]-2-methyl-thieno[3,2-d]pyrimidin-4-amine;
N-[(E)-(1-hydroxy-3,4-dihydro-2,1-benzoxaborinin-6-yl)methyleneamino]-N-isobutyl-1,1-dioxo-1,2-benzothiazol-3-amine;
N-[(E)-(1-hydroxy-4,5-dihydro-3H-2,1-benzoxaborepin-7-yl)methyleneamino]-N-isobutyl-1,1-dioxo-1,2-benzothiazol-3-amine;
N-[(E)-(1-hydroxy-7-methoxy-3H-2,1-benzoxaborol-5-yl)methyleneamino]-N-isobutyl-1,1-dioxo-1,2-benzothiazol-3-amine;
N-[(E)-(1-hydroxy-3-methyl-3H-2,1-benzoxaborol-5-yl)methyleneamino]-N-isobutyl-1,1-dioxo-1,2-benzothiazol-3-amine;
N-[(E)-(1-hydroxy-3-methyl-3H-2,1-benzoxaborol-5-yl)methyleneamino]-N-methyl-1,1-dioxo-1,2-benzothiazol-3-amine;
N-[(E)-(1-hydroxy-3H-2,1-benzoxaborol-5-yl)methyleneamino]-N-methyl-1,1-dioxo-4,5,6,7-tetrahydro-1,2-benzothiazol-3-amine;
3-[6-(1-hydroxy-3H-2,1-benzoxaborol-5-yl)-3-methyl-4,5-dihydro-3H-pyridazin-2-yl]-1,2-benzothiazole 1,1-dioxide;
4-[6-(1-hydroxy-3H-2,1-benzoxaborol-5-yl)-3-methyl-4,5-dihydro-3H-pyridazin-2-yl]-8-methoxy-quinazoline;
N-[(E)-(1-hydroxy-3H-2,1-benzoxaborol-5-yl)methyleneamino]-5-methoxy-N-methyl-pyridazin-3-amine;
N-[(E)-(1-hydroxy-3H-2,1-benzoxaborol-5-yl)methyleneamino]-N-methyl-2-methylsulfanyl-thiazolo[4,5-d]pyrimidin-7-amine;
N-[(E)-(1-hydroxy-3H-2,1-benzoxaborol-5-yl)methyleneamino]-N,1-dimethyl-pyrazolo[3,4-d]pyrimidin-4-amine;
N-[(E)-(1-hydroxy-3H-2,1-benzoxaborol-5-yl)methyleneamino]-N,7-dimethyl-thieno[3,2-d]pyrimidin-4-amine;
N-ethyl-N-[(E)-(1-hydroxy-3H-2,1-benzoxaborol-5-yl)methyleneamino]-1H-pyrazolo[4,3-d]pyrimidin-7-amine;
N7-ethyl-N7-[(E)-(1-hydroxy-3H-2,1-benzoxaborol-5-yl)methyleneamino]-N2,N2-dimethyl-thiazolo[4,5-d]pyrimidine-2,7-diamine;
N-ethyl-N-[(E)-(1-hydroxy-3H-2,1-benzoxaborol-5-yl)methyleneamino]-3-methyl-1H-pyrazolo[4,3-d]pyrimidin-7-amine;
N-ethyl-N-[(E)-(1-hydroxy-3H-2,1-benzoxaborol-5-yl)methyleneamino]-5H-pyrrolo[3,2-d]pyrimidin-4-amine;
N-ethyl-N-[(E)-(1-hydroxy-3H-2,1-benzoxaborol-5-yl)methyleneamino]-2-morpholino-thiazolo[4,5-d]pyrimidin-7-amine;
N-ethyl-N-[(E)-(1-hydroxy-3H-2,1-benzoxaborol-5-yl)methyleneamino]-2-methylsulfanyl-thiazolo[4,5-d]pyrimidin-7-amine;
N-ethyl-N-[(E)-(1-hydroxy-3H-2,1-benzoxaborol-5-yl)methyleneamino]-7-propyl-pyrrolo[2,3-d]pyrimidin-4-amine;
N,7-diethyl-N-[(E)-(1-hydroxy-3H-2,1-benzoxaborol-5-yl) methylene amino]pyrrolo[2,3-d]pyrimidin-4-amine;
N-ethyl-N-[(E)-(1-hydroxy-3H-2,1-benzoxaborol-5-yl)methyleneamino]-1H-pyrazolo[3,4-d]pyrimidin-4-amine;
N-ethyl-N-[(E)-(1-hydroxy-3H-2,1-benzoxaborol-5-yl)methyleneamino]thiazolo[4,5-d]pyrimidin-7-amine;
N-ethyl-N-[(E)-(1-hydroxy-3H-2,1-benzoxaborol-5-yl)methyleneamino]-2,7-dimethyl-thieno[3,2-d]pyrimidin-4-amine;
N-ethyl-7-fluoro-N-[(E)-(1-hydroxy-3H-2,1-benzoxaborol-5-yl)methyleneamino]quinazolin-4-amine;
N-ethyl-N-[(E)-(1-hydroxy-3H-2,1-benzoxaborol-5-yl)methyleneamino]-6-methyl-thieno[3,2-d]pyrimidin-4-amine;
N-ethyl-N-[(E)-(1-hydroxy-3H-2,1-benzoxaborol-5-yl)methyleneamino]-6,7,8,9-tetrahydrobenzothiopheno[3,2-d]pyrimidin-4-amine;
N-[(E)-(1-hydroxy-3H-2,1-benzoxaborol-5-yl)methyleneamino]-N-isobutyl-2-methylsulfanyl-thiazolo[4,5-d]pyrimidin-7-amine;
N-[(E)-(1-hydroxy-3H-2,1-benzoxaborol-5-yl)methyleneamino]-N-isobutyl-7-methyl-thieno[3,2-d]pyrimidin-4-amine;
N-[(E)-(1-hydroxy-3H-2,1-benzoxaborol-5-yl)methyleneamino]-N-(2-methoxyethyl)-7-methyl-thieno[3,2-d]pyrimidin-4-amine;
N-[(E)-(1-hydroxy-3H-2,1-benzoxaborol-5-yl)methyleneamino]-N-(2-methoxyethyl)-2-methylsulfanyl-thiazolo[4,5-d]pyrimidin-7-amine;
N-[(E)-(1-hydroxy-3H-2,1-benzoxaborol-5-yl)methyleneamino]-N-(3-methoxypropyl)-2-methylsulfanyl-thiazolo[4,5-d]pyrimidin-7-amine;
2-[[(E)-(1-hydroxy-3H-2,1-benzoxaborol-5-yl)methyleneamino]-(7-methylthieno[3,2-d]pyrimidin-4-yl)amino]ethanol;
6-[[(E)-(1-hydroxy-3H-2,1-benzoxaborol-5-yl)methyleneamino]-methyl-amino]-9-methyl-7H-purin-8-one;
4-[[(E)-(1-hydroxy-3H-2,1-benzoxaborol-5-yl)methyleneamino]-methyl-amino]-7-methyl-5H-pyrrolo[2,3-d]pyrimidin-6-one;
4-[[(E)-(1-hydroxy-3H-2,1-benzoxaborol-5-yl)methyleneamino]-methyl-amino]-6,8-dihydro-5H-pyrido[2,3-d]pyrimidin-7-one;
N-[(E)-(1-hydroxy-3H-2,1-benzoxaborol-5-yl)methyleneamino]-N-methyl-5,6-dihydrofuro[2,3-d]pyrimidin-4-amine;
N-[(E)-(1-hydroxy-3H-2,1-benzoxaborol-5-yl)methyleneamino]-N-methyl-7-phenyl-thieno[3,2-d]pyrimidin-4-amine;
7-cyclopropyl-N-[(E)-(1-hydroxy-3H-2,1-benzoxaborol-5-yl)methyleneamino]-N-methyl-thieno[3,2-d]pyrimidin-4-amine;
N-[(E)-(1-hydroxy-3H-2,1-benzoxaborol-5-yl)methyleneamino]-N-methyl-7-morpholino-thieno[3,2-d]pyrimidin-4-amine;
7-ethyl-N-[(E)-(1-hydroxy-3H-2,1-benzoxaborol-5-yl)methyleneamino]-N-methyl-thieno[3,2-d]pyrimidin-4-amine;
N-[(E)-(1-hydroxy-3H-2,1-benzoxaborol-5-yl)methyleneamino]-N,7-dimethyl-5,6-dihydropyrrolo[2,3-d]pyrimidin-4-amine;
9-cyclobutyl-6-[[(E)-(1-hydroxy-3H-2,1-benzoxaborol-5-yl)methyleneamino]-methyl-amino]-7H-purin-8-one;
6-[[(E)-(1-hydroxy-3H-2,1-benzoxaborol-5-yl)methyleneamino]-methyl-amino]-9-[3-(methoxymethyl)cyclobutyl]-7H-purin-8-one;
6-[[(E)-(1-hydroxy-3H-2,1-benzoxaborol-5-yl)methyleneamino]-methyl-amino]-9-(3-hydroxycyclobutyl)-7H-purin-8-one;
9-(3-bicyclo[1.1.1]pentanyl)-6-[[(E)-(1-hydroxy-3H-2,1-benzoxaborol-5-yl)methyleneamino]-methyl-amino]-7H-purin-8-one;
7-cyclobutyl-4-[[(E)-(1-hydroxy-3H-2,1-benzoxaborol-5-yl)methyleneamino]-methyl-amino]-5H-pyrrolo[2,3-d]pyrimidin-6-one;
4-[ethyl-[(E)-(1-hydroxy-3H-2,1-benzoxaborol-5-yl)methyleneamino]amino]-N-propyl-thieno[3,2-d]pyrimidine-7-carboxamide;
4-[ethyl-[(E)-(1-hydroxy-3H-2,1-benzoxaborol-5-yl)methyleneamino]amino]-N,N-dimethyl-thieno[3,2-d]pyrimidine-7-carboxamide;
N,N-dibutyl-4-[ethyl-[(E)-(1-hydroxy-3H-2,1-benzoxaborol-5-yl)methyleneamino]-amino]thieno[3,2-d]pyrimidine-7-carboxamide;
4-[ethyl-[(E)-(1-hydroxy-3H-2,1-benzoxaborol-5-yl)methyleneamino]amino]-N-(oxetan-3-yl)thieno[3,2-d]pyrimidine-7-carboxamide;
4-[ethyl-[(E)-(1-hydroxy-3H-2,1-benzoxaborol-5-yl)methyleneamino]amino]-N-(4-methoxybutyl)thieno[3,2-d]pyrimidine-7-carboxamide;
4-[6-(1-hydroxy-3H-2,1-benzoxaborol-5-yl)-3-methyl-4,5-dihydro-3H-pyridazin-2-yl]furo[2,3-d]pyrimidine;
4-[6-(1-hydroxy-3H-2,1-benzoxaborol-5-yl)-3-methyl-4,5-dihydro-3H-pyridazin-2-yl]-7-methyl-thieno[3,2-d]pyrimidine;
(+) 4-[6-(1-hydroxy-3H-2,1-benzoxaborol-5-yl)-3-methyl-4,5-dihydro-3H-pyridazin-2-yl]-7-methyl-thieno[3,2-d]pyrimidine;
(−) 4-[6-(1-hydroxy-3H-2,1-benzoxaborol-5-yl)-3-methyl-4,5-dihydro-3H-pyridazin-2-yl]-7-methyl-thieno[3,2-d]pyrimidine;
4-[6-(1-hydroxy-3H-2,1-benzoxaborol-5-yl)-3-methyl-4,5-dihydro-3H-pyridazin-2-yl]thieno[3,2-d]pyrimidine;
4-[6-(1-hydroxy-3H-2,1-benzoxaborol-5-yl)-3-methyl-4,5-dihydro-3H-pyridazin-2-yl]-6,7,8,9-tetrahydrobenzothiopheno[3,2-d]pyrimidine;
7-[6-(1-hydroxy-3H-2,1-benzoxaborol-5-yl)-3-methyl-4,5-dihydro-3H-pyridazin-2-yl]-2-methylsulfanyl-thiazolo[4,5-d]pyrimidine;
N-[(E)-(1-hydroxy-3H-2,1-benzoxaborol-5-yl)methyleneamino]-7-(methoxymethyl)-N-methyl-thieno[3,2-d]pyrimidin-4-amine; and
pharmaceutically acceptable salts thereof.

### Claim 9 (depends on 1)

A pharmaceutical composition comprising a compound of claim 1, or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable excipient.

### Claim 10 (depends on 1)

A method of treating a cancer where YAP is localized in the nucleus of the tumor cells, which comprises administering to a subject in need thereof a compound of claim 1, or a pharmaceutically acceptable salt thereof.

### Claim 11 (depends on 10)

The method of claim 10, wherein the cancer is lung cancer, thyroid cancer, ovarian cancer, colorectal cancer, prostate cancer, pancreas cancer, esophagus cancer, liver cancer, breast cancer or skin cancer.

### Claim 12 (depends on 10)

The method of claim 10, wherein the cancer is malignant mesothelioma.

### Claim 13 (depends on 5)

A pharmaceutical composition comprising a compound of claim 5, or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable excipient.

### Claim 14 (depends on 8)

A pharmaceutical composition comprising a compound of claim 8, or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable excipient.

### Claim 15 (depends on 5)

A method of treating a cancer where YAP is localized in the nucleus of the tumor cells, which comprises administering to a subject in need thereof a compound of claim 5, or a pharmaceutically acceptable salt thereof.

### Claim 16 (depends on 15)

The method of claim 15, wherein the cancer is malignant mesothelioma.

### Claim 17 (depends on 8)

A method of treating a cancer where YAP is localized in the nucleus of the tumor cells, which comprises administering to a subject in need thereof a compound of claim 8, or a pharmaceutically acceptable salt thereof.

### Claim 18 (depends on 17)

The method of claim 17, wherein the cancer is malignant mesothelioma.

### Claim 19 (depends on 2)

The compound of claim 2, or a pharmaceutically acceptable salt thereof, wherein
is a group of formula (VI):