US 2024/0254140 A1Published application

Compounds and their use in the treatment of bacterial infection

AssigneeHoffmann-La Roche Inc.

InventorsDaniele ANDREOTTI, John G. CUMMING, Giacomo FOSSATI, Susanna SAMPAOLESI, Elena SERRA

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Abstract

The invention provides novel compounds having the general formula (I) wherein R1, R2, R3a, R3b, R4, A1, A2, A3, A4, A5, A6, B1, B2, B3, B4, and L are as described herein, compositions including the compounds and methods of using the compounds.

Claims32

Dependent claims

A compound of formula (I)

wherein
A1 is —N—;
A2 is selected from
i) —N—, and
ii) —CH—;
A3 is —CH—;
A4 is selected from
i) —O—, and
ii) —S—;
A5 is —CH—;
A6 is —O—;
B1 is selected from
i) —N—, and
ii) —CR5—;
B2 is selected from
i) —N—, and
ii) —CR6—;
B3 is —CNH—C(═O)R7—;
B4 is selected from
i) —N—, and
ii) —CR8—;
R2 is H;
R3a is selected from
i) H,
ii) halogen, and
iii) OH;
R3b is selected from
i) H,
ii) halogen, and
iii) OH;
wherein at least one of R3a and R3b is H;
R4 is selected from
i) H,
ii) halogen,
iii) C1-6-alkoxy, and
iii) OH;
R5 is selected from
i) H,
ii) halogen,
iii) cyano, and
iv) C1-6-alkyl;
R6 is selected from
i) H, and
ii) C1-6-alkyl;
R7 is selected from
i) CRaRbNRcRd,
ii) CRaRbOH,
iii) CHReRf,
iv) heterocycloalkyl,
v) heterocycloalkylalkyl,
vi) substituted heterocycloalkyl,
vii) substituted heterocycloalkylalkyl, and
vii) substituted heteroaryl,
wherein substituted heterocycloalkyl, substituted heterocycloalkylalkyl or substituted heteroaryl is substituted by 1 to 2 substituents independently selected from C1-6-alkyl, C1-6-alkoxy, OH, hydroxyalkyl, amino, and dialkylamino, or two substituents together form a 3-to-6-membered cycloalkyl ring;
R8 is selected from
i) H,
ii) halogen, and
iii) cyano;
L is -L1-NR9-L2-;
L1 is (CH2)x, wherein x represents an integer of 1 to 6;
L2 is (CH2)y, wherein y represents an integer of 1 to 6,
R1 is H and R9 is selected from
i) H, and
ii) C1-6-alkyl;
or R1, R9 and L2 and the atoms to which they are bonded form a 4-6-membered heterocycle ring comprising a single N heteroatom;
or R1 and L2 and the atoms to which they are bonded form a 3-6-membered cycloalkyl ring;
Ra and Rb are independently selected from
iv) H,
v) C1-6-alkyl, and
vi) halogen,
or Ra and Rb form a 3-membered cycloalkyl ring;
Rc and Rd are independently selected from
i) H,
ii) C1-6-alkyl,
iii) C3-C6-cycloalkyl, and
iv) 4-6-membered heterocycloalkyl comprising a single oxygen heteroatom,
or Rc and Rd form a 4 membered ring comprising a single N heteroatom;
Re and Rf are independently selected from
i) H,
ii) NH2,
iii) hydroxyalkyl, and
iv) alkyl-COOH;
or pharmaceutically acceptable salts thereof.

80 more elements

A compound selected from

2-(dimethylamino)-N-[7-fluoro-2-[[2-[2-oxo-3-(3-oxo-4H-pyrazino[2,3-b][1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino]methyl]indan-5-yl]acetamide;
1-(dimethylamino)-N-[7-fluoro-2-[[2-[2-oxo-3-(3-oxo-4H-pyrazino[2,3-b][1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino]methyl]indan-5-yl]cyclopropanecarboxamide;
2-(dimethylamino)-N-[7-fluoro-2-[[2-[2-oxo-3-(3-oxo-4H-pyrazino[2,3-b][1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino]methyl]indan-5-yl]-2-methyl-propanamide;
(2R)-2-(dimethylamino)-N-[7-fluoro-2-[[2-[2-oxo-3-(3-oxo-4H-pyrazino[2,3-b][1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino]methyl]indan-5-yl]propanamide;
N-[7-fluoro-2-[[2-[2-oxo-3-(3-oxo-4H-pyrazino[2,3-b][1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino]methyl]indan-5-yl]-2-morpholino-acetamide;
2-(dimethylamino)-N-[7-fluoro-2-[[2-oxo-3-(3-oxo-4H-pyrazino[2,3-b][1,4]oxazin-6-yl)-1-oxa-3,8-diazaspiro[4.5]decan-8-yl]methyl]indan-5-yl]-2-methyl-propanamide;
(2R)-2-(dimethylamino)-N-[7-fluoro-2-[[2-oxo-3-(3-oxo-4H-pyrazino[2,3-b][1,4]oxazin-6-yl)-1-oxa-3,8-diazaspiro[4.5]decan-8-yl]methyl]indan-5-yl]propanamide;
2-(azetidin-1-yl)-N-[7-fluoro-2-[[2-[2-oxo-3-(3-oxo-4H-pyrazino[2,3-b][1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino]methyl]indan-5-yl]acetamide;
(2S)-2-(dimethylamino)-N-[7-fluoro-2-[[2-[2-oxo-3-(3-oxo-4H-pyrazino[2,3-b][1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino]methyl]indan-5-yl]propanamide;
(2S)—N-[7-fluoro-2-[[2-[2-oxo-3-(3-oxo-4H-pyrazino[2,3-b][1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino]methyl]indan-5-yl]-1-methyl-pyrrolidine-2-carboxamide;
N-[7-fluoro-2-[[2-[2-oxo-3-(3-oxo-4H-pyrazino[2,3-b][1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino]methyl]indan-5-yl]-2-[methyl(oxetan-3-yl)amino]acetamide;
2-(3-azabicyclo[3.1.0]hexan-3-yl)-N-[7-fluoro-2-[[2-[2-oxo-3-(3-oxo-4H-pyrazino[2,3-b][1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino]methyl]indan-5-yl]acetamide;
2-[cyclopropyl(methyl)amino]-N-[7-fluoro-2-[[2-[2-oxo-3-(3-oxo-4H-pyrazino[2,3-b][1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino]methyl]indan-5-yl]acetamide;
(2R)—N-[7-fluoro-2-[[2-[2-oxo-3-(3-oxo-4H-pyrazino[2,3-b][1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino]methyl]indan-5-yl]-1-methyl-pyrrolidine-2-carboxamide;
N-[7-fluoro-2-[[2-[2-oxo-3-(3-oxo-4H-pyrazino[2,3-b][1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino]methyl]indan-5-yl]-2-methyl-oxazole-5-carboxamide;
2-(azetidin-1-yl)-N-[7-fluoro-2-[[2-[(5R)-2-oxo-3-(3-oxo-4H-pyrazino[2,3-b][1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino]methyl]indan-5-yl]propanamide;
(2S,4R)—N-[7-fluoro-2-[[2-[2-oxo-3-(3-oxo-4H-pyrazino[2,3-b][1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino]methyl]indan-5-yl]-4-methoxy-1-methyl-pyrrolidine-2-carboxamide;
N-[7-fluoro-2-[[2-[2-oxo-3-(3-oxo-4H-pyrazino[2,3-b][1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino]methyl]indan-5-yl]-2-hydroxy-2-methyl-propanamide;
(3R)-3-(dimethylamino)-N-[7-fluoro-2-[[2-[2-oxo-3-(3-oxo-4H-pyrazino[2,3-b][1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino]methyl]indan-5-yl]tetrahydrofuran-3-carboxamide;
N-[7-cyano-2-[[2-[2-oxo-3-(3-oxo-4H-pyrazino[2,3-b][1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino]methyl]indan-5-yl]-2-hydroxy-2-methyl-propanamide;
N-[7-cyano-2-[[2-[2-oxo-3-(3-oxo-4H-pyrido[3,2-b][1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino]methyl]indan-5-yl]-2-hydroxy-2-methyl-propanamide;
(2R)—N-[7-cyano-2-[[2-[(5R)-2-oxo-3-(3-oxo-4H-pyrazino[2,3-b][1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino]methyl]indan-5-yl]-2-(dimethylamino)propanamide;
(2R)-2-(dimethylamino)-N-[4-fluoro-2-[[2-[2-oxo-3-(3-oxo-4H-pyrazino[2,3-b][1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino]methyl]indan-5-yl]propanamide;
2-(dimethylamino)-N-[4-methyl-6-[[2-[2-xo-3-(3-oxo-4H-pyrazino[2,3-b][1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino]methyl]-6,7-dihydro-5H-cyclopenta[b]pyridin-2-yl]acetamide;
(2R)-2-(dimethylamino)-N-[4-methyl-6-[[2-[2-oxo-3-(3-oxo-4H-pyrazino[2,3-b][1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino]methyl]-6,7-dihydro-5H-cyclopenta[b]pyridin-2-yl]propanamide;
2-(azetidin-1-yl)-N-[4-methyl-6-[[2-[2-oxo-3-(3-oxo-4H-pyrazino[2,3-b][1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino]methyl]-6,7-dihydro-5H-cyclopenta[b]pyridin-2-yl]acetamide;
(2S)-1-methyl-N-[4-methyl-6-[[2-[2-oxo-3-(3-oxo-4H-pyrazino[2,3-b][1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino]methyl]-6,7-dihydro-5H-cyclopenta[b]pyridin-2-yl]pyrrolidine-2-carboxamide;
(2R)-2-(dimethylamino)-N-[1-methyl-6-[[2-[2-oxo-3-(3-oxo-4H-pyrazino[2,3-b][1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino]methyl]-6,7-dihydro-5H-cyclopenta[c]pyridin-3-yl]propanamide;
(2R)-2-(dimethylamino)-N-[1-methyl-6-[[2-oxo-3-(3-oxo-4H-pyrazino[2,3-b][1,4]oxazin-6-yl)-1-oxa-3,8-diazaspiro[4.5]decan-8-yl]methyl]-6,7-dihydro-5H-cyclopenta[c]pyridin-3-yl]propanamide;
(2R)—N-[4,7-difluoro-2-hydroxy-2-[[2-[2-oxo-3-(3-oxo-4H-pyrazino[2,3-b][1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino]methyl]indan-5-yl]-2-(dimethylamino)propanamide;
(2R)—N-[4,7-difluoro-2-methoxy-2-[[2-[2-oxo-3-(3-oxo-4H-pyrazino[2,3-b][1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino]methyl]indan-5-yl]-2-(dimethylamino)propanamide;
(2R)-2-(dimethylamino)-N-[2,4,7-trifluoro-2-[[2-[2-oxo-3-(3-oxo-4H-pyrazino[2,3-b][1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino]methyl]indan-5-yl]propanamide;
(2R)—N-[2,7-difluoro-2-[[2-[2-oxo-3-(3-oxo-4H-pyrazino[2,3-b][1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino]methyl]indan-5-yl]-2-(dimethylamino)propanamide;
(2R)—N-[7-cyano-2-hydroxy-2-[[2-[2-oxo-3-(3-oxo-4H-pyrazino[2,3-b][1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino]methyl]indan-5-yl]-2-(dimethylamino)propanamide;
(2R)—N-[7-cyano-2-hydroxy-2-[[2-oxo-3-(3-oxo-4H-pyrazino[2,3-b][1,4]oxazin-6-yl)-1-oxa-3,8-diazaspiro[4.5]decan-8-yl]methyl]indan-5-yl]-2-(dimethylamino)propanamide;
(2S)—N-[7-fluoro-2-[[2-[2-oxo-3-(3-oxo-4H-pyrazino[2,3-b][1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino]methyl]indan-5-yl]pyrrolidine-2-carboxamide;
(2S,4R)—N-[7-fluoro-2-[[2-[2-oxo-3-(3-oxo-4H-pyrazino[2,3-b][1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino]methyl]indan-5-yl]-4-hydroxy-pyrrolidine-2-carboxamide;
(2R)-2-amino-N-[7-fluoro-2-[[2-[2-oxo-3-(3-oxo-4H-pyrazino[2,3-b][1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino]methyl]indan-5-yl]-3-hydroxy-propanamide;
(2R)-2-amino-N-[7-fluoro-2-[[2-[2-oxo-3-(3-oxo-4H-pyrazino[2,3-b][1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino]methyl]indan-5-yl]-3-methoxy-propanamide;
(3R)-3-amino-N-[7-fluoro-2-[[2-[2-oxo-3-(3-oxo-4H-pyrazino[2,3-b][1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino]methyl]indan-5-yl]tetrahydrofuran-3-carboxamide;
(3R)-3-amino-N-[7-fluoro-2-[[2-[2-oxo-3-(3-oxo-4H-pyrazino[2,3-b][1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino]methyl]indan-5-yl]tetrahydrofuran-3-carboxamide;
2,2,2-trifluoroacetic acid;
(3S)-3-amino-N-[7-fluoro-2-[[2-[2-oxo-3-(3-oxo-4H-pyrazino[2,3-b][1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino]methyl]indan-5-yl]tetrahydrofuran-3-carboxamide;
(3S)-3-amino-N-[7-fluoro-2-[[2-[2-oxo-3-(3-oxo-4H-pyrazino[2,3-b][1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino]methyl]indan-5-yl]tetrahydrofuran-3-carboxamide;
hydrochloride;
(2S,4R)—N-[7-fluoro-2-[[2-oxo-3-(3-oxo-4H-pyrazino[2,3-b][1,4]oxazin-6-yl)-1-oxa-3,8-diazaspiro[4.5]decan-8-yl]methyl]indan-5-yl]-4-hydroxy-pyrrolidine-2-carboxamide;
2-amino-N-[7-fluoro-2-[[2-[2-oxo-3-(3-oxo-4H-pyrazino[2,3-b][1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino]methyl]indan-5-yl]-2-methyl-propanamide;
(2S,4R)—N-[7-fluoro-2-[[2-[2-oxo-3-(3-oxo-4H-pyrazino[2,3-b][1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino]methyl]indan-5-yl]-4-methoxy-pyrrolidine-2-carboxamide;
(2R,4R)—N-[7-fluoro-2-[[2-[2-oxo-3-(3-oxo-4H-pyrazino[2,3-b][1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino]methyl]indan-5-yl]-4-hydroxy-pyrrolidine-2-carboxamide;
(2S,4S)—N-[7-fluoro-2-[[2-[2-oxo-3-(3-oxo-4H-pyrazino[2,3-b][1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino]methyl]indan-5-yl]-4-hydroxy-pyrrolidine-2-carboxamide;
(2R,4S)—N-[7-fluoro-2-[[2-[2-oxo-3-(3-oxo-4H-pyrazino[2,3-b][1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino]methyl]indan-5-yl]-4-hydroxy-pyrrolidine-2-carboxamide;
(3S)-3-amino-4-[[7-fluoro-2-[[2-[2-oxo-3-(3-oxo-4H-pyrazino[2,3-b][1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino]methyl]indan-5-yl]amino]-4-oxo-butanoic acid;
(3S)-3-amino-4-[[7-fluoro-2-[[2-[2-oxo-3-(3-oxo-4H-pyrazino[2,3-b][1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino]methyl]indan-5-yl]amino]-4-oxo-butanoic acid;
2,2,2-trifluoroacetic acid;
(2S,4R)—N-[7-fluoro-2-[[2-[2-oxo-3-(3-oxo-4H-pyrazino[2,3-b][1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino]methyl]indan-5-yl]-4-hydroxy-1-methyl-pyrrolidine-2-carboxamide;
N-[7-fluoro-2-[[2-[2-oxo-3-(3-oxo-4H-pyrazino[2,3-b][1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino]methyl]indan-5-yl]-2-[(3R)-3-hydroxypyrrolidin-1-yl]acetamide;
(2S)-2-(dimethylamino)-N-[7-fluoro-2-[[2-oxo-3-(3-oxo-4H-pyrazino[2,3-b][1,4]oxazin-6-yl)-1-oxa-3,8-diazaspiro[4.5]decan-8-yl]methyl]indan-5-yl]propanamide;
(2S,4R)—N-[4,7-difluoro-2-[[2-oxo-3-(3-oxo-4H-pyrazino[2,3-b][1,4]oxazin-6-yl)-1-oxa-3,8-diazaspiro[4.5]decan-8-yl]methyl]indan-5-yl]-4-hydroxy-pyrrolidine-2-carboxamide;
(2R)—N-[7-fluoro-2-[[2-oxo-3-(3-oxo-4H-pyrazino[2,3-b][1,4]oxazin-6-yl)-1-oxa-3,8-diazaspiro[4.5]decan-8-yl]methyl]indan-5-yl]-2-(hydroxymethyl)pyrrolidine-2-carboxamide;
(2R)—N-[7-fluoro-2-[[2-oxo-3-(3-oxo-4H-pyrazino[2,3-b][1,4]oxazin-6-yl)-1-oxa-3,8-diazaspiro[4.5]decan-8-yl]methyl]indan-5-yl]-2-(hydroxymethyl)pyrrolidine-2-carboxamide;
2,2,2-trifluoroacetic acid;
(2S,3S)—N-[7-fluoro-2-[[2-oxo-3-(3-oxo-4H-pyrazino[2,3-b][1,4]oxazin-6-yl)-1-oxa-3,8-diazaspiro[4.5]decan-8-yl]methyl]indan-5-yl]-3-hydroxy-pyrrolidine-2-carboxamide;
(2S,3S)—N-[7-fluoro-2-[[2-oxo-3-(3-oxo-4H-pyrazino[2,3-b][1,4]oxazin-6-yl)-1-oxa-3,8-diazaspiro[4.5]decan-8-yl]methyl]indan-5-yl]-3-hydroxy-pyrrolidine-2-carboxamide;
2,2,2-trifluoroacetic acid;
(2R,4R)—N-[7-fluoro-2-[[2-oxo-3-(3-oxo-4H-pyrazino[2,3-b][1,4]oxazin-6-yl)-1-oxa-3,8-diazaspiro[4.5]decan-8-yl]methyl]indan-5-yl]-4-hydroxy-pyrrolidine-2-carboxamide;
(2R,4S)—N-[7-fluoro-2-[[2-oxo-3-(3-oxo-4H-pyrazino[2,3-b][1,4]oxazin-6-yl)-1-oxa-3,8-diazaspiro[4.5]decan-8-yl]methyl]indan-5-yl]-4-hydroxy-pyrrolidine-2-carboxamide;
(2S,4S)—N-[7-fluoro-2-[[2-oxo-3-(3-oxo-4H-pyrazino[2,3-b][1,4]oxazin-6-yl)-1-oxa-3,8-diazaspiro[4.5]decan-8-yl]methyl]indan-5-yl]-4-hydroxy-pyrrolidine-2-carboxamide;
(2R)-2-(dimethylamino)-N-[7-fluoro-2-[[methyl-[2-[2-oxo-3-(3-oxo-4H-pyrazino[2,3-b][1,4]oxazin-6-yl)oxazolidin-5-yl]ethyl]amino]methyl]indan-5-yl]propanamide;
(2S,4R)—N-[7-cyano-2-[[2-oxo-3-(3-oxo-4H-pyrazino[2,3-b][1,4]oxazin-6-yl)-1-oxa-3,8-diazaspiro[4.5]decan-8-yl]methyl]indan-5-yl]-4-hydroxy-pyrrolidine-2-carboxamide;
(2S,4R)-4-hydroxy-N-[6-[[2-oxo-3-(3-oxo-4H-pyrazino[2,3-b][1,4]oxazin-6-yl)-1-oxa-3,8-diazaspiro[4.5]decan-8-yl]methyl]-6,7-dihydro-5H-cyclopenta[b]pyridin-3-yl]pyrrolidine-2-carboxamide;
(2S,4R)—N-[7-cyano-2-[[2-[2-oxo-3-(3-oxo-4H-pyrazino[2,3-b][1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino]methyl]indan-5-yl]-4-hydroxy-pyrrolidine-2-carboxamide;
(2R)—N-[7-cyano-2-[[2-[2-oxo-3-(3-oxo-4H-pyrazino[2,3-b][1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino]methyl]indan-5-yl]-1-methyl-pyrrolidine-2-carboxamide;
(2S,4R)—N-[7-fluoro-2-[[methyl-[2-[2-oxo-3-(3-oxo-4H-pyrazino[2,3-b][1,4]oxazin-6-yl)oxazolidin-5-yl]ethyl]amino]methyl]indan-5-yl]-4-hydroxy-pyrrolidine-2-carboxamide;
(2S,4R)—N-[7-fluoro-2-[[2-oxo-3-(3-oxo-4H-pyrazino[2,3-b][1,4]oxazin-6-yl)-1-oxa-3,8-diazaspiro[4.5]decan-8-yl]methyl]indan-5-yl]-4-hydroxy-1-methyl-pyrrolidine-2-carboxamide;
(2R)-2-(dimethylamino)-N-[7-fluoro-3-hydroxy-2-[[2-oxo-3-(3-oxo-4H-pyrazino[2,3-b][1,4]oxazin-6-yl)-1-oxa-3,8-diazaspiro[4.5]decan-8-yl]methyl]indan-5-yl]propanamide;
(2R)-2-(dimethylamino)-N-[7-fluoro-3-hydroxy-2-[[2-[(5R)-2-oxo-3-(3-oxo-4H-pyrazino[2,3-b][1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino]methyl]indan-5-yl]propanamide;
(2R)—N-[3,7-difluoro-2-[[2-[(5R)-2-oxo-3-(3-oxo-4H-pyrazino[2,3-b][1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino]methyl]indan-5-yl]-2-(dimethylamino)propanamide;
(2R)-2-(dimethylamino)-N-[7-fluoro-2-[[2-[(5S)-2-oxo-3-(3-oxo-4H-pyrazino[2,3-b][1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino]methyl]indan-5-yl]propanamide;
(2R)-2-(dimethylamino)-N-[7-fluoro-2-[[2-[(5R)-2-oxo-3-(3-oxo-4H-pyrazino[2,3-b][1,4]oxazin-6-yl)oxazolidin-5-yl]ethylamino]methyl]indan-5-yl]propanamide;
or pharmaceutically acceptable salts thereof.

77 more elements

Dependencies are inferred from the claim text.

Facts

Application: 18/609,825Filed 19 Mar 2024
Priority: EP 21197649.320 Sep 2021
Published: 1 Aug 2024
Term ends: Not estimatedThe source records don’t support an estimate.

Classification20 codes

C07D 413/14
Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms:…
C07D 498/04
In which the condensed system contains two hetero rings: ortho-condensed systems
A61K 9/08
Medicinal preparations characterised by special physical form: solutions
A61K 9/2013
Excipients; Inactive ingredients: organic compounds, e.g. phospholipids, fats

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Abstract

A compound of formula (I)

wherein
A1 is —N—;
A2 is selected from
i) —N—, and
ii) —CH—;
A3 is —CH—;
A4 is selected from
i) —O—, and
ii) —S—;
A5 is —CH—;
A6 is —O—;
B1 is selected from
i) —N—, and
ii) —CR5—;
B2 is selected from
i) —N—, and
ii) —CR6—;
B3 is —CNH—C(═O)R7—;
B4 is selected from
i) —N—, and
ii) —CR8—;
R2 is H;
R3a is selected from
i) H,
ii) halogen, and
iii) OH;
R3b is selected from
i) H,
ii) halogen, and
iii) OH;
wherein at least one of R3a and R3b is H;
R4 is selected from
i) H,
ii) halogen,
iii) C1-6-alkoxy, and
iii) OH;
R5 is selected from
i) H,
ii) halogen,
iii) cyano, and
iv) C1-6-alkyl;
R6 is selected from
i) H, and
ii) C1-6-alkyl;
R7 is selected from
i) CRaRbNRcRd,
ii) CRaRbOH,
iii) CHReRf,
iv) heterocycloalkyl,
v) heterocycloalkylalkyl,
vi) substituted heterocycloalkyl,
vii) substituted heterocycloalkylalkyl, and
vii) substituted heteroaryl,
wherein substituted heterocycloalkyl, substituted heterocycloalkylalkyl or substituted heteroaryl is substituted by 1 to 2 substituents independently selected from C1-6-alkyl, C1-6-alkoxy, OH, hydroxyalkyl, amino, and dialkylamino, or two substituents together form a 3-to-6-membered cycloalkyl ring;
R8 is selected from
i) H,
ii) halogen, and
iii) cyano;
L is -L1-NR9-L2-;
L1 is (CH2)x, wherein x represents an integer of 1 to 6;
L2 is (CH2)y, wherein y represents an integer of 1 to 6,
R1 is H and R9 is selected from
i) H, and
ii) C1-6-alkyl;
or R1, R9 and L2 and the atoms to which they are bonded form a 4-6-membered heterocycle ring comprising a single N heteroatom;
or R1 and L2 and the atoms to which they are bonded form a 3-6-membered cycloalkyl ring;
Ra and Rb are independently selected from
iv) H,
v) C1-6-alkyl, and
vi) halogen,
or Ra and Rb form a 3-membered cycloalkyl ring;
Rc and Rd are independently selected from
i) H,
ii) C1-6-alkyl,
iii) C3-C6-cycloalkyl, and
iv) 4-6-membered heterocycloalkyl comprising a single oxygen heteroatom,
or Rc and Rd form a 4 membered ring comprising a single N heteroatom;
Re and Rf are independently selected from
i) H,
ii) NH2,
iii) hydroxyalkyl, and
iv) alkyl-COOH;
or pharmaceutically acceptable salts thereof.

80 more elements

Facts

Application

18/609,825Filed 19 Mar 2024

Priority

EP 21197649.320 Sep 2021

Published

1 Aug 2024

Term ends

Not estimatedThe source records don’t support an estimate.

Classification20 codes

C07D 413/14
Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms:…
C07D 498/04
In which the condensed system contains two hetero rings: ortho-condensed systems
A61K 9/08
Medicinal preparations characterised by special physical form: solutions
A61K 9/2013
Excipients; Inactive ingredients: organic compounds, e.g. phospholipids, fats