IP Library › Granted Patent US 12,486,285
Granted Patent B2
US 12,486,285 · App. 17/968,159 · Granted Dec 2, 2025

BCL6 inhibitors

Inventors: Benjamin Richard Bellenie (London, GB); Kwai Ming Jack Cheung (London, GB); Owen Alexander Davis (London, GB); Swen Hoelder (London, GB); Rosemary Huckvale (London, GB); Gavin Collie (London, GB); Mirco Meniconi (London, GB); Alfie Brennan (London, GB); Matthew Garth Lloyd (London, GB)
Assignees: CANCER RESEARCH TECHNOLOGY LIMITED; The Institute of Cancer Research: Royal Cancer Hospital
C07D498/04A61P35/00C07D471/04C07D498/14C07D498/20C07D513/04C07D519/00
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Quick Facts
Patent No.
US 12,486,285
App. No.
17/968,159
Granted
Dec 2, 2025
Kind
B2
Abstract

The present invention relates to compounds of formula I that function as inhibitors of BCL6 (B-cell lymphoma 6) activity: wherein X 1 , X 2 , R 1 , R 2 , R 30 , R 31 and Ring A are each as defined herein. The present invention also relates to processes for the preparation of these compounds, to pharmaceutical compositions comprising them, and to their use in the treatment of proliferative disorders, such as cancer, as well as other diseases or conditions in which BCL6 activity is implicated.

Claims (158)

1 . A compound of Formula (II):

or a salt, hydrate or solvate thereof, wherein:

X 1 is selected from N or CR a , wherein R a is selected from hydrogen, (1-2C) alkyl, halogen, (1-2C) alkoxy, (1-2C) haloalkyl, (1-2C) haloalkoxy, cyano or NR b R c , wherein R b and R c are each independently selected from hydrogen or (1-2C) alkyl;

X 2 is selected from N, CH, CF, CCl or C—CH 3 ;

R 1 is selected from hydrogen or a group of the formula:

-L-Y—Z

wherein:

L is absent or (1-3C) alkylene;

Y is absent or O, C(O), C(O)O or C(O)N(R e ), wherein R e is selected from hydrogen or (1-4C) alkyl; and

Z is hydrogen, (1-6C) alkyl, aryl, (3-6C) cycloalkyl, (3-6C) cycloalkenyl, 5 or 6 membered heteroaryl or 4 to 7 membered heterocyclyl; wherein Z is optionally further substituted by one or more substituent groups independently selected from oxo, (1-2C) alkyl, halo, (1-2C) haloalkyl, (1-2C) haloalkoxy, (1-2C) aminoalkyl, cyano, NR g R h or OR g ; wherein R g and R h are each independently selected from hydrogen or (1-4° C.) alkyl;

R 30 is selected from (1-4C) alkyl, (3-6C) cycloalkyl, (1-4C) haloalkyl or cyano, wherein each (1-4C) alkyl and/or (3-6C) cycloalkyl substituent is optionally further substituted by one or more substituents selected from (1-4C) alkyl, (3-6C) cycloalkyl, hydroxy, (1-2C) alkoxy, NR u R v , (1-2C) aminoalkyl or halo, wherein R u and R v are independently selected from hydrogen or (1-2C) alkyl;

R 31 is selected from hydrogen, (1-4C) alkyl, cyano, (1-4C) haloalkyl or a group of the formula:

Y 5 -L 5 -Z 5

wherein:

Y 5 is absent or selected from C(O)O or C(O)N(R w ), wherein R w is selected from hydrogen or (1-2C) alkyl;

L 5 is absent or (1-2C) alkylene; and

Z 5 is hydrogen, (1-6C) alkyl, aryl, (3-6C) cycloalkyl, 5 or 6 membered heteroaryl or 4 to 6-membered heterocyclyl; wherein Z 5 is optionally substituted by one or more substituents selected from (1-2C) alkyl, halo, (1-2C) haloalkyl, (1-2C) haloalkoxy, (1-2C) alkoxy, NH 2 , cyano, nitro or hydroxy; or

R 30 and R 31 are linked such that, together with the carbon atom to which they are attached, they form a 4-6 membered carbocyclic ring or a heterocyclic ring; and

Ring A is a 6- or 7-membered heterocyclic ring, which, in addition to the substituent groups R 30 and R 31 , is optionally further substituted by one or more substituent groups selected from oxo, (1-2C) alkyl, cyclopropyl, spiro-cyclopropyl, halo, (1-2C) haloalkyl, (1-2C) haloalkoxy, (1-2C) alkoxy, NH 2 , cyano or hydroxy.

2 . The compound of claim 1 , wherein R 1 is selected from hydrogen or a group of the formula:

-L-Z

wherein:

L is absent or (1-3C) alkylene; and

Z is (1-6C) alkyl, aryl, (3-6C) cycloalkyl, (3-6C) cycloalkenyl, 5 or 6 membered heteroaryl or 5 or 6 membered heterocyclyl; wherein Z is optionally further substituted by one or more substituent groups independently selected from oxo, (1-2C) alkyl, halo, (1-2C) haloalkyl, (1-2C) haloalkoxy, (1-2C) aminoalkyl, cyano, NR g R h or OR g ; wherein R g and R h are each independently selected from hydrogen or (1-2C) alkyl.

3 . The compound of claim 1 , wherein R 30 is selected from (1-4C) alkyl, (3-6C) cycloalkyl, (1-4C) haloalkyl, or cyano, wherein each (1-4C) alkyl and/or (3-6C) cycloalkyl substituent is optionally further substituted by one or more substituents selected from (1-4C) alkyl, cyclopropyl, hydroxy, (1-2C) alkoxy or halo.

4 . The compound of claim 1 , wherein Ring A is a 7-membered heterocyclic ring, which, in addition to the substituent groups R 30 and R 31 , is optionally further substituted by one or more substituent groups selected from oxo, (1-2C) alkyl, cyclopropyl, fluoro, (1-2C) fluorooalkyl, (1-2C) alkoxy, or cyano.

5 . The compound of claim 1 , wherein the compound is selected from the group consisting of:

(S)-10-amino-2,7-dimethyl-1,2,3,4-tetrahydro-[1,4]oxazepino [2,3-c]quinolin-6 (7H)-one;

(R)-10-amino-2,7-dimethyl-1,2,3,4-tetrahydro-[1,4]oxazepino [2,3-c]quinolin-6 (7H)-one;

10-amino-2-ethyl-7-methyl-1,2,3,4-tetrahydro-[1,4]oxazepino [2,3-c]quinolin-6 (7H)-one;

(S)-10-amino-2-cyclopropyl-7-methyl-1,2,3,4-tetrahydro-[1,4]oxazepino [2,3-c]quinoline-6 (7H)-one;

(R)-10-amino-2-cyclopropyl-7-methyl-1,2,3,4-tetrahydro-[1,4]oxazepino [2,3-c]quinoline-6 (7H)-one;

10-amino-2,3,3,7-tetramethyl-1,2,3,4-tetrahydro-[1,4]oxazepino [2,3-c]quinoline-6 (7H)-one;

10′-amino-2′,7′-dimethyl-1′,2′-dihydro-4′H-spiro [cyclopropane-1,3′-[1,4]oxazepino [2,3-c]quinolin]-6′ (7′H)-one;

(2S,4S)-10-amino-2,4,7-trimethyl-1,2,3,4-tetrahydro-[1,4]-oxazepino [2,3-c]quinoline-6 (7H)-one;

10-amino-2-cyclopropyl-3,3-difluoro-7-methyl-1,2,3,4-tetrahydro-[1,4]oxazepino [2,3-c]quinoline-6 (7H)-one;

(S)-10-amino-2-cyclopropyl-3,3-difluoro-7-methyl-1,2,3,4-tetrahydro-[1,4]oxazepino [2,3-c]quinolin-6 (7H)-one;

10-amino-2,2,7-trimethyl-1,2,3,4-tetrahydro-[1,4]oxazepino [2,3-c]quinolin-6 (7H)-one;

10-amino-2-(methoxymethyl)-2,7-dimethyl-1,2,3,4-tetrahydro-[1,4]oxazepino [2,3-c]quinolin-6 (7H)-one;

10′-amino-7′-methyl-3′,4,4′,5-tetrahydro-1′H,2H-spiro [furan-3,2′-[1,4]oxazepino [2,3-c]quinolin]-6′ (7′H)-one;

10-amino-2-(difluoromethyl)-7-methyl-1,2,3,4-tetrahydro-[1,4]oxazepino [2,3-c]quinolin-6 (7H)-one;

(R)-10-amino-2-cyclopropyl-7-(cyclopropylmethyl)-1,2,3,4-tetrahydro [1,4]oxazepino [2,3-c]quinolin-6 (7H)-one;

(R)-10-amino-2-cyclopropyl-7-((3,3-difluorocyclobutyl) methyl)-1,2,3,4-tetrahydro-[1,4]oxazepino [2,3-c]quinolin-6 (7H)-one;

(R)-10-amino-2-cyclopropyl-1,2,3,4-tetrahydro-[1,4]oxazepino [2,3-c]quinolin-6 (7H)-one; and

(R)-10-amino-2-cyclopropyl-7-methyl-1,2,3,4-tetrahydro-[1,4]oxazepino [2,3-c][1,8]naphthyridin-6 (7H)-one,

or a salt, hydrate or solvate thereof.

6 . The compound of claim 1 , wherein the compound is(S)-10-amino-2-cyclopropyl-3,3-difluoro-7-methyl-1,2,3,4-tetrahydro-[1,4]oxazepino [2,3-c]quinolin-6 (7H)-one.

7 . A compound of Formula (III):

or a salt, hydrate or solvate thereof, wherein:

W is NO 2 , halogen, or OTf;

X 1 is selected from N or CR a , wherein R a is selected from hydrogen, (1-2C) alkyl, halogen, (1-2C) alkoxy, (1-2C) haloalkyl, (1-2C) haloalkoxy, cyano or NR b R c , wherein R b and R c are each independently selected from hydrogen or (1-2C) alkyl;

X 2 is selected from N, CH, CF, CCl or C—CH 3 ;

R 1 is selected from hydrogen or a group of the formula:

-L-Y—Z

wherein:

L is absent or (1-3C) alkylene;

Y is absent or O, C(O), C(O)O or C(O)N(R c ), wherein R c is selected from hydrogen or (1-4C) alkyl; and

Z is hydrogen, (1-6C) alkyl, aryl, (3-6C) cycloalkyl, (3-6C) cycloalkenyl, 5 or 6 membered heteroaryl or 4 to 7 membered heterocyclyl; wherein Z is optionally further substituted by one or more substituent groups independently selected from oxo, (1-2C) alkyl, halo, (1-2C) haloalkyl, (1-2C) haloalkoxy, (1-2C) aminoalkyl, cyano, NR g R h or OR g ; wherein R g and R h are each independently selected from hydrogen or (1-4C) alkyl;

R 30 is selected from (1-4C) alkyl, (3-6C) cycloalkyl, (1-4C) haloalkyl or cyano, wherein each (1-4C) alkyl and/or (3-6C) cycloalkyl substituent is optionally further substituted by one or more substituents selected from (1-4C) alkyl, (3-6C) cycloalkyl, hydroxy, (1-2C) alkoxy, NR u R v , (1-2C) aminoalkyl or halo, wherein R u and R v are independently selected from hydrogen or (1-2C) alkyl;

R 31 is selected from hydrogen, (1-4C) alkyl, cyano, (1-4C) haloalkyl or a group of the formula:

Y 5 -L 5 -Z 5

wherein:

Y 5 is absent or selected from C(O)O or C(O)N(R w ), wherein R w is selected from hydrogen or (1-2C) alkyl;

L 5 is absent or (1-2C) alkylene; and

Z 5 is hydrogen, (1-6C) alkyl, aryl, (3-6C) cycloalkyl, 5 or 6 membered heteroaryl or 4 to 6-membered heterocyclyl; wherein Z 5 is optionally substituted by one or more substituents selected from (1-2C) alkyl, halo, (1-2C) haloalkyl, (1-2C) haloalkoxy, (1-2C) alkoxy, NH 2 , cyano, nitro or hydroxy; or

R 30 and R 31 are linked such that, together with the carbon atom to which they are attached, they form a 4-6 membered carbocyclic ring or a heterocyclic ring; and

Ring A is a 6- or 7-membered heterocyclic ring, which, in addition to the substituent groups R 30 and R 31 , is optionally further substituted by one or more substituent groups selected from oxo, (1-2C) alkyl, cyclopropyl, spiro-cyclopropyl, halo, (1-2C) haloalkyl, (1-2C) haloalkoxy, (1-2C) alkoxy, NH 2 , cyano or hydroxy.

8 . The compound of claim 7 , wherein R 1 is selected from hydrogen or a group of the formula:

-L-Z

wherein:

L is absent or (1-3C) alkylene; and

Z is (1-6C) alkyl, aryl, (3-6C) cycloalkyl, (3-6C) cycloalkenyl, 5 or 6 membered heteroaryl or 5 or 6 membered heterocyclyl; wherein Z is optionally further substituted by one or more substituent groups independently selected from oxo, (1-2C) alkyl, halo, (1-2C) haloalkyl, (1-2C) haloalkoxy, (1-2C) aminoalkyl, cyano, NR g R h or OR g ; wherein R g and R h are each independently selected from hydrogen or (1-2C) alkyl.

9 . The compound of claim 7 , wherein R 30 is selected from (1-4C) alkyl, (3-6C) cycloalkyl, (1-4C) haloalkyl, or cyano, wherein each (1-4C) alkyl and/or (3-6C) cycloalkyl substituent is optionally further substituted by one or more substituents selected from (1-4C) alkyl, cyclopropyl, hydroxy, (1-2C) alkoxy or halo.

10 . The compound of claim 7 , wherein Ring A is a 7-membered heterocyclic ring, which, in addition to the substituent groups R 30 and R 31 , is optionally further substituted by one or more substituent groups selected from oxo, (1-2C) alkyl, cyclopropyl, fluoro, (1-2C) fluorooalkyl, (1-2C) alkoxy or cyano.

11 . The compound of claim 7 , wherein W is NO 2 .

12 . The compound of claim 7 , wherein the compound is a compound of Formula (III-a):

wherein:

Z is an (1-2C) alkylene group selected from (—CH 2 —), (—CH 2 CH 2 —), (—CF 2 CH 2 ) and (—CH (Me) CH 2 —);

W is selected from the group consisting of NO 2 , halogen, and OTf;

X 1 is selected from N or CR a , wherein R a is selected from hydrogen, (1-2C) alkyl, halogen, (1-2C) alkoxy, (1-2C) haloalkyl, (1-2C) haloalkoxy, cyano or NR b R c , wherein R b and R c are each independently selected from hydrogen or (1-2C) alkyl;

X 2 is selected from N, CH, CF, CCl or C—CH 3 ;

R 1 is selected from hydrogen or a group of the formula:

-L-Y—Z

wherein:

L is absent or (1-3C) alkylene;

Y is absent or O, C(O), C(O)O or C(O)N(R e ), wherein R e is selected from hydrogen or (1-4C) alkyl; and

Z is hydrogen, (1-6C) alkyl, aryl, (3-6C) cycloalkyl, (3-6C) cycloalkenyl, 5 or 6 membered heteroaryl or 4 to 7 membered heterocyclyl; wherein Z is optionally further substituted by one or more substituent groups independently selected from oxo, (1-2C) alkyl, halo, (1-2C) haloalkyl, (1-2C) haloalkoxy, (1-2C) aminoalkyl, cyano, NR g R h or OR g ; wherein R g and R h are each independently selected from hydrogen or (1-4C) alkyl;

R 30 is selected from (1-4C) alkyl, (3-6C) cycloalkyl, (1-4C) haloalkyl or cyano, wherein each (1-4C) alkyl and/or (3-6C) cycloalkyl substituent is optionally further substituted by one or more substituents selected from (1-4C) alkyl, (3-6C) cycloalkyl, hydroxy, (1-2C) alkoxy, NR u R v , (1-2C) aminoalkyl or halo, wherein R u and R v are independently selected from hydrogen or (1-2C) alkyl;

R 31 is selected from hydrogen, (1-4C) alkyl, cyano, (1-4C) haloalkyl or a group of the formula:

Y 5 -L 5 -Z 5

wherein:

Y 5 is absent or selected from C(O)O or C(O)N(R w ), wherein R w is selected from hydrogen or (1-2C) alkyl;

L 5 is absent or (1-2C) alkylene; and

Z 5 is hydrogen, (1-6C) alkyl, aryl, (3-6C) cycloalkyl, 5 or 6 membered heteroaryl or 4 to 6-membered heterocyclyl; wherein Z 5 is optionally substituted by one or more substituents selected from (1-2C) alkyl, halo, (1-2C) haloalkyl, (1-2C) haloalkoxy, (1-2C) alkoxy, NH 2 , cyano, nitro or hydroxy; or

R 30 and R 31 are linked such that, together with the carbon atom to which they are attached, they form a 4-6 membered carbocyclic ring or a heterocyclic ring.

13 . The compound of claim 7 , wherein W is NO 2 .

14 . The compound of claim 7 , wherein the compound is selected from the group consisting of:

(R)-2-cyclopropyl-7-(cyclopropylmethyl)-10-nitro-1,2,3,4-tetrahydro-[1,4]oxazepino-[2,3-c]quinolin-6 (7H)-one;

(R)-2-cyclopropyl-10-nitro-1,2,3,4-tetrahydro-[1,4]oxazepino [2,3-c]quinolin-6 (7H)-one;

2,2,7-trimethyl-10-nitro-1,2,3,4-tetrahydro-[1,4]oxazepino [2,3-c]quinolin-6 (7H)-one;

(S)-2-cyclopropyl-3,3-difluoro-7-methyl-10-nitro-1,2,3,4-tetrahydro-[1,4]oxazepino-[2,3-c]quinolin-6 (7H)-one; and

(S)-2,7-dimethyl-10-nitro-1,2,3,4-tetrahydro-[1,4]oxazepino [2,3-c]quinolin-6 (7H)-one, or a salt, hydrate or solvate thereof.

15 . The compound of claim 7 , wherein the compound is(S)-2-cyclopropyl-3,3-difluoro-7-methyl-10-nitro-1,2,3,4-tetrahydro-[1,4]oxazepino-[2,3-c]quinolin-6 (7H)-one.

16 . A process of synthesising a compound of Formula (II) from a compound of Formula (III):

the process comprising reducing the W group of Formula (III) to provide the compound of Formula (II), wherein:

W is NO 2 ;

X 1 is selected from N or CR a , wherein R a is selected from hydrogen, (1-2C) alkyl, halogen, (1-2C) alkoxy, (1-2C) haloalkyl, (1-2C) haloalkoxy, cyano or NR b R c , wherein R b and R c are each independently selected from hydrogen or (1-2C) alkyl;

X 2 is selected from N, CH, CF, CCl or C—CH 3 ;

R 1 is selected from hydrogen or a group of the formula:

-L-Y—Z

wherein:

L is absent or (1-3C) alkylene;

Y is absent or O, C(O), C(O)O or C(O)N(R c ), wherein R c is selected from hydrogen or (1-4C) alkyl; and

Z is hydrogen, (1-6C) alkyl, aryl, (3-6C) cycloalkyl, (3-6C) cycloalkenyl, 5 or 6 membered heteroaryl or 4 to 7 membered heterocyclyl; wherein Z is optionally further substituted by one or more substituent groups independently selected from oxo, (1-2C) alkyl, halo, (1-2C) haloalkyl, (1-2C) haloalkoxy, (1-2C) aminoalkyl, cyano, NR g R h or OR g ; wherein R g and R h are each independently selected from hydrogen or (1-4° C.) alkyl;

R 30 is selected from (1-4C) alkyl, (3-6C) cycloalkyl, (1-4C) haloalkyl or cyano, wherein each (1-4C) alkyl and/or (3-6C) cycloalkyl substituent is optionally further substituted by one or more substituents selected from (1-4C) alkyl, (3-6C) cycloalkyl, hydroxy, (1-2C) alkoxy, NR u R v , (1-2C) aminoalkyl or halo, wherein R u and R v are independently selected from hydrogen or (1-2C) alkyl;

R 31 is selected from hydrogen, (1-4C) alkyl, cyano, (1-4C) haloalkyl or a group of the formula:

Y 5 -L 5 -Z 5

wherein:

Y 5 is absent or selected from C(O)O or C(O)N(R w ), wherein R w is selected from hydrogen or (1-2C) alkyl;

L 5 is absent or (1-2C) alkylene; and

Z 5 is hydrogen, (1-6C) alkyl, aryl, (3-6C) cycloalkyl, 5 or 6 membered heteroaryl or 4 to 6-membered heterocyclyl; wherein Z 5 is optionally substituted by one or more substituents selected from (1-2C) alkyl, halo, (1-2C) haloalkyl, (1-2C) haloalkoxy, (1-2C) alkoxy, NH 2 , cyano, nitro or hydroxy; or

R 30 and R 31 are linked such that, together with the carbon atom to which they are attached, they form a 4-6 membered carbocyclic ring or a heterocyclic ring; and

Ring A is a 6- or 7-membered heterocyclic ring, which, in addition to the substituent groups R 30 and R 31 , is optionally further substituted by one or more substituent groups selected from oxo, (1-2C) alkyl, cyclopropyl, spiro-cyclopropyl, halo, (1-2C) haloalkyl, (1-2C) haloalkoxy, (1-2C) alkoxy, NH 2 , cyano or hydroxy.

17 . The process of claim 16 , wherein reducing the W group comprises: (1) hydrogenation in the presence of a metal catalyst; (2) reaction with tin (II) chloride; or (3) reaction with iron or zinc metal.

18 . The process of claim 16 , wherein R 1 is selected from hydrogen or a group of the formula:

-L-Z

wherein:

L is absent or (1-3C) alkylene; and

Z is (1-6C) alkyl, aryl, (3-6C) cycloalkyl, (3-6C) cycloalkenyl, 5 or 6 membered heteroaryl or 5 or 6 membered heterocyclyl; wherein Z is optionally further substituted by one or more substituent groups independently selected from oxo, (1-2C) alkyl, halo, (1-2C) haloalkyl, (1-2C) haloalkoxy, (1-2C) aminoalkyl, cyano, NR g R h or OR g ; wherein R g and R h are each independently selected from hydrogen or (1-2C) alkyl;

R 30 is selected from (1-4C) alkyl, (3-6C) cycloalkyl, (1-4C) haloalkyl, or cyano, wherein each (1-4C) alkyl and/or (3-6C) cycloalkyl substituent is optionally further substituted by one or more substituents selected from (1-4C) alkyl, cyclopropyl, hydroxy, (1-2C) alkoxy or halo; and

Ring A is a 7-membered heterocyclic ring, which, in addition to the substituent groups R 30 and R 31 , is optionally further substituted by one or more substituent groups selected from oxo, (1-2C) alkyl, cyclopropyl, fluoro, (1-2C) fluorooalkyl, (1-2C) alkoxy or cyano.

19 . The process of 44, wherein the compound of Formula (II) is selected from the group consisting of:

(S)-10-amino-2,7-dimethyl-1,2,3,4-tetrahydro-[1,4]oxazepino [2,3-c]quinolin-6 (7H)-one;

(R)-10-amino-2,7-dimethyl-1,2,3,4-tetrahydro-[1,4]oxazepino [2,3-c]quinolin-6 (7H)-one;

10-amino-2-ethyl-7-methyl-1,2,3,4-tetrahydro-[1,4]oxazepino [2,3-c]quinolin-6 (7H)-one;

(S)-10-amino-2-cyclopropyl-7-methyl-1,2,3,4-tetrahydro-[1,4]oxazepino [2,3-c]quinoline-6 (7H)-one;

(R)-10-amino-2-cyclopropyl-7-methyl-1,2,3,4-tetrahydro-[1,4]oxazepino [2,3-c]quinoline-6 (7H)-one;

10-amino-2,3,3,7-tetramethyl-1,2,3,4-tetrahydro-[1,4]oxazepino [2,3-c]quinoline-6 (7H)-one;

10′-amino-2′,7′-dimethyl-1′,2′-dihydro-4′H-spiro [cyclopropane-1,3′-[1,4]oxazepino [2,3-c]quinolin]-6′ (7′H)-one;

(2S,4S)-10-amino-2,4,7-trimethyl-1,2,3,4-tetrahydro-[1,4]-oxazepino [2,3-c]quinoline-6 (7H)-one;

10-amino-2-cyclopropyl-3,3-difluoro-7-methyl-1,2,3,4-tetrahydro-[1,4]oxazepino [2,3-c]quinoline-6 (7H)-one;

(S)-10-amino-2-cyclopropyl-3,3-difluoro-7-methyl-1,2,3,4-tetrahydro-[1,4]oxazepino [2,3-c]quinolin-6 (7H)-one;

10-amino-2,2,7-trimethyl-1,2,3,4-tetrahydro-[1,4]oxazepino [2,3-c]quinolin-6 (7H)-one;

10-amino-2-(methoxymethyl)-2,7-dimethyl-1,2,3,4-tetrahydro-[1,4]oxazepino [2,3-c]quinolin-6 (7H)-one;

10′-amino-7′-methyl-3′,4,4′,5-tetrahydro-1′H,2H-spiro [furan-3,2′-[1,4]oxazepino [2,3-c]quinolin]-6′ (7′H)-one;

10-amino-2-(difluoromethyl)-7-methyl-1,2,3,4-tetrahydro-[1,4]oxazepino [2,3-c]quinolin-6 (7H)-one;

(R)-10-amino-2-cyclopropyl-7-(cyclopropylmethyl)-1,2,3,4-tetrahydro [1,4]oxazepino [2,3-c]quinolin-6 (7H)-one;

(R)-10-amino-2-cyclopropyl-7-((3,3-difluorocyclobutyl) methyl)-1,2,3,4-tetrahydro-[1,4]oxazepino [2,3-c]quinolin-6 (7H)-one;

(R)-10-amino-2-cyclopropyl-1,2,3,4-tetrahydro-[1,4]oxazepino [2,3-c]quinolin-6 (7H)-one; and

(R)-10-amino-2-cyclopropyl-7-methyl-1,2,3,4-tetrahydro-[1,4]oxazepino [2,3-c][1,8]naphthyridin-6 (7H)-one.

20 . The process of claim 16 , wherein the compound of Formula (II) is(S)-10-amino-2-cyclopropyl-3,3-difluoro-7-methyl-1,2,3,4-tetrahydro-[1,4]oxazepino [2,3-c]quinolin-6 (7H)-one.

21 . The process of claim 16 , wherein the compound of Formula (III) is selected from the group consisting of:

(R)-2-cyclopropyl-7-(cyclopropylmethyl)-10-nitro-1,2,3,4-tetrahydro-[1,4]oxazepino-[2,3-c]quinolin-6 (7H)-one;

(R)-2-cyclopropyl-10-nitro-1,2,3,4-tetrahydro-[1,4]oxazepino [2,3-c]quinolin-6 (7H)-one;

2,2,7-trimethyl-10-nitro-1,2,3,4-tetrahydro-[1,4]oxazepino [2,3-c]quinolin-6 (7H)-one;

(S)-2-cyclopropyl-3,3-difluoro-7-methyl-10-nitro-1,2,3,4-tetrahydro-[1,4]oxazepino-[2,3-c]quinolin-6 (7H)-one; and

(S)-2,7-dimethyl-10-nitro-1,2,3,4-tetrahydro-[1,4]oxazepino [2,3-c]quinolin-6 (7H)-one.

22 . The compound of claim 16 , wherein the compound of Formula (III) is(S)-2-cyclopropyl-3,3-difluoro-7-methyl-10-nitro-1,2,3,4-tetrahydro-[1,4]oxazepino-[2,3-c]quinolin-6 (7H)-one.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 23, 2023
From: BELLENIE, BENJAMIN RICHARD; BRENNAN, ALFIE; CHEUNG, KWAI MING JACK; COLLIE, GAVIN; DAVIS, OWEN ALEXANDER; HOELDER, SWEN; HUCKVALE, ROSEMARY; LLOYD, MATTHEW GARTH; MENICONI, MIRCO
To: THE INSTITUTE OF CANCER RESEARCH: ROYAL CANCER HOSPITAL; CANCER RESEARCH TECHNOLOGY LIMITED
Reel/Frame 062785/0255 →
Priority Claims (2)
GB 1806132.5 · Apr 13, 2018 · national
GB 1819136.1 · Nov 23, 2018 · national
Continuity (2)
Continuation 17046650
Related Publication 20230287003A1 · Sep 14, 2023
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