US 2026/0085077 A1Published application

Heterocyclic derivatives as janus kinase inhibitors

AssigneeChiesi Farmaceutici S.p.A.

InventorsAlessandro ACCETTA, Alberto CUZZOLIN, Fabio RANCATI, Andrea RIZZI, Ivaylo Jivkov ELENKOV, Milan MESIC, Ela RADOŠEVIC

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Abstract

The present invention relates to a compounds of general formula (I) inhibiting the JAK family of non-receptor tyrosine protein kinases (JAK1, JAK2, JAK3, and TYK2); methods of preparing such compounds, pharmaceutical compositions containing them and therapeutic use thereof. The compounds of the invention may be useful in the treatment of diseases or conditions associated with a dysregulation of the JAK family non-receptor kinases; in particular for the treatment of various inflammatory diseases including asthma, COPD and other respiratory diseases.

Claims14

Dependent claims

A compound of formula I
wherein:
R1 is a heteroaryl group selected from the group consisting of imidazo[1,2-b]pyridazin-3-yl, pyrazolo[1,5-a]pyrimidin-3-yl and 3-oxo-(3,4-dihydropyrazin-2-yl)amino;
R2 is a group of formula
that is a substituent group linked to the molecule scaffold,
wherein
V is a bond or is a divalent group selected from the group consisting of O, S, N(R6), C(O)N(R6), N(R6)C(O);
N(R6)C(O)O;
N(R6)S(O)2;
and N(R6)C(O)N(R6);
Q is selected from the group consisting of H, (C1-C6)alkyl, (C1-C6)hydroxyalkyl, (C1-C6)alkoxy, —(CH2)mNR4R5, (C3-C8)cycloalkyl, (C3-C10)heterocycloalkyl;
—S—(C3-C6)heterocycloalkyl, and —N(R6)—(C3-C6)heterocycloalkyl;
wherein said (C3-C8)cycloalkyl and (C3-C10)heterocycloalkyl are further optionally substituted by one or more substituent selected from the group consisting of —OH, oxo, (C1-C10)alkyl, (C1-C6)alkoxy;
halogen, (C1-C6)haloalkyl, alkanoyl, (C1-C6)hydroxyalkyl, (C1-C6)alkoxy(C1-C6)alkyl, —N(R6)(CH2)mC(O)NR4R5, —(CO)NR4R5, —(CH2)mNR4R5, (C3-C8)cycloalkyl(C1-C6)alkyl;
(C3-C6)heterocycloalkyl(C1-C6)alkyl, (C3-C6)heterocycloalkyl and hydroxyl-(C3-C6)heterocycloalkyl;
R3 is a bicyclic moiety which is a substituent group linked to the scaffold graphically represented by
wherein the dashed line indicates a single or a double bond;
X is selected from the group consisting of N, S, and C;
Y is selected from the group consisting of Cand N;
Z is selected from the group consisting of C, N, and O;
K is a bond or selected from the group consisting of O, C, and S;
G is a bond or selected from the group consisting of C and O;
is the point of attachment of a substituent group to the rest of the molecule;
n and m are in each occurrence independently 0, 1, 2, 3 or 4;
R4 and R5 are each independently selected from the group consisting of
—H,
(C1-C6)alkyl,
(C1-C6)haloalkyl, and
(C3-C6)heterocycloalkyl;
R6 is in each occurrence independently selected from the group consisting of H, (C1-C6)alkyl and (C1-C6)hydroxyalkyl;
R7 is one or more group in each occurrence independently selected from the group consisting of —OH, oxo, (C1-C6)alkyl, halogen, (C1-C6)haloalkyl, (C1-C6)hydroxyalkyl, —(CH2)mNR4R5, (C1-C6)alkyl-S(O)2— and (C1-C6)alkyl-S(O)2N(R6)—;
and
R8 is selected from the group consisting of (C1-C6)alkoxy and (C1-C6)haloalkoxy;
a single enantiomer, a diastereoisomer, a mixture thereof in any proportion,
or a pharmaceutically acceptable salt or solvate thereof.

32 more elements

The compound, single enantiomer, diastereoisomer, mixture thereof, or pharmaceutically acceptable salt or solvate thereof, according to claim 1, wherein the compound is selected from the group consisting of:
6-(difluoromethoxy)-7-(3-methyl-6-(pyrazolo[1,5-a]pyrimidin-3-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine,
1-(6-methoxy-2-(methylsulfonyl)isoindolin-5-yl)-3-methyl-6-(pyrazolo[1,5-a]pyrimidin-3-yl)-1H-pyrazolo[4,3-c]pyridine,
8-methoxy-7-(3-methyl-6-(pyrazolo[1,5-a]pyrimidin-3-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)-1,3,4,5-tetrahydro-2H-benzo[b]azepin-2-one,
7-methoxy-6-(3-methyl-6-(pyrazolo[1,5-a]pyrimidin-3-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)-3,4-dihydroquinolin-2 (1H)-one,
7-methoxy-6-(3-methyl-6-(pyrazolo[1,5-a]pyrimidin-3-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)-2,3-dihydroquinolin-4 (1H)-one,
6-methoxy-7-(3-methyl-6-(pyrazolo[1,5-a]pyrimidin-3-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)-3,4-dihydro-2H-benzo[b][1,4]thiazine,
6-methoxy-7-(3-methyl-6-(pyrazolo[1,5-a]pyrimidin-3-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)-2H-benzo[b][1,4]thiazin-3 (4H)-one,
6-methoxy-7-(3-methyl-6-(pyrazolo[1,5-a]pyrimidin-3-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)-3,4-dihydro-2H-benzo[b][1,4]thiazine 1,1-dioxide,
7-methoxy-8-(3-methyl-6-(pyrazolo[1,5-a]pyrimidin-3-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepine,
6-methoxy-5-(3-methyl-6-(pyrazolo[1,5-a]pyrimidin-3-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)indolin-2-one,
2,2-difluoro-6-methoxy-7-(3-methyl-6-(pyrazolo[1,5-a]pyrimidin-3-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)-2H-benzo[b][1,4]oxazin-3 (4H)-one,
7-methoxy-3-methyl-6-(3-methyl-6-(pyrazolo[1,5-a]pyrimidin-3-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)-3,4-dihydroquinazolin-2 (1H)-one,
1-(6-methoxy-3,4-dihydro-2H-benzo[b][1,4]oxazin-7-yl)-6-(pyrazolo[1,5-a]pyrimidin-3-yl)-N-(1-((tetrahydro-2H-pyran-4-yl)methyl)azetidin-3-yl)-1H-pyrazolo[4,3-c]pyridine-3-carboxamide,
N-(3-(4,4-difluoropiperidin-1-yl)propyl)-1-(6-methoxy-3,4-dihydro-2H-benzo[b][1,4]oxazin-7-yl)-6-(pyrazolo[1,5-a]pyrimidin-3-yl)-1H-pyrazolo[4,3-c]pyridine-3-carboxamide,
1-(6-methoxy-3,4-dihydro-2H-benzo[b][1,4]oxazin-7-yl)-N-(2-(2-oxo-1-oxa-8-azaspiro[4.5]decan-8-yl)ethyl)-6-(pyrazolo[1,5-a]pyrimidin-3-yl)-1H-pyrazolo[4,3-c]pyridine-3-carboxamide,
N-(3-(dimethylamino)propyl)-1-(6-methoxy-3,4-dihydro-2H-benzo[b][1,4]thiazin-7-yl)-6-(pyrazolo[1,5-a]pyrimidin-3-yl)-1H-pyrazolo[4,3-c]pyridine-3-carboxamide,
1-(6-methoxy-3,4-dihydro-2H-benzo[b][1,4]thiazin-7-yl)-N-(1-methylazetidin-3-yl)-6-(pyrazolo[1,5-a]pyrimidin-3-yl)-1H-pyrazolo[4,3-c]pyridine-3-carboxamide,
(R)-1-(6-methoxy-3,4-dihydro-2H-benzo[b][1,4]thiazin-7-yl)-N-((4-methylmorpholin-2-yl)methyl)-6-(pyrazolo[1,5-a]pyrimidin-3-yl)-1H-pyrazolo[4,3-c]pyridine-3-carboxamide,
3-(2-oxomorpholino)propyl (1-(6-methoxy-3,4-dihydro-2H-benzo[b][1,4]thiazin-7-yl)-6-(pyrazolo[1,5-a]pyrimidin-3-yl)-1H-pyrazolo[4,3-c]pyridin-3-yl)carbamate,
2-(methyl(2-oxotetrahydrofuran-3-yl)amino)ethyl (1-(6-methoxy-3,4-dihydro-2H-benzo[b][1,4]thiazin-7-yl)-6-(pyrazolo[1,5-a]pyrimidin-3-yl)-1H-pyrazolo[4,3-c]pyridin-3-yl)carbamate,
(R)-1-(6-methoxy-3-oxo-3,4-dihydro-2H-benzo[b][1,4]thiazin-7-yl)-N-((4-methylmorpholin-2-yl)methyl)-6-(pyrazolo[1,5-a]pyrimidin-3-yl)-1H-pyrazolo[4,3-c]pyridine-3-carboxamide,
(S)-1-(6-methoxy-3-oxo-3,4-dihydro-2H-benzo[b][1,4]thiazin-7-yl)-N-((4-methylmorpholin-2-yl)methyl)-6-(pyrazolo[1,5-a]pyrimidin-3-yl)-1H-pyrazolo[4,3-c]pyridine-3-carboxamide,
N-(3-(dimethylamino)propyl)-1-(6-methoxy-3-oxo-3,4-dihydro-2H-benzo[b][1,4]thiazin-7-yl)-6-(pyrazolo[1,5-a]pyrimidin-3-yl)-1H-pyrazolo[4,3-c]pyridine-3-carboxamide,
N-(3-(dimethylamino)propyl)-1-(7-methoxy-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)-6-(pyrazolo[1,5-a]pyrimidin-3-yl)-1H-pyrazolo[4,3-c]pyridine-3-carboxamide,
N-(3-(dimethylamino)propyl)-1-(7-methoxy-1,2,3,4-tetrahydroquinolin-6-yl)-6-(pyrazolo[1,5-a]pyrimidin-3-yl)-1H-pyrazolo[4,3-c]pyridine-3-carboxamide,
7-methoxy-6-(3-(methylamino)-6-(pyrazolo[1,5-a]pyrimidin-3-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)-3,4-dihydroquinolin-2 (1H)-one,
2-(dimethylamino)ethyl (1-(7-methoxy-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)-6-(pyrazolo[1,5-a]pyrimidin-3-yl)-1H-pyrazolo[4,3-c]pyridin-3-yl)carbamate,
2-(dimethylamino)ethyl (1-(6-methoxy-3,4-dihydro-2H-benzo[b][1,4]thiazin-7-yl)-6-(pyrazolo[1,5-a]pyrimidin-3-yl)-1H-pyrazolo[4,3-c]pyridin-3-yl)carbamate,
2-morpholinoethyl (1-(6-methoxy-3,4-dihydro-2H-benzo[b][1,4]thiazin-7-yl)-6-(pyrazolo[1,5-a]pyrimidin-3-yl)-1H-pyrazolo[4,3-c]pyridin-3-yl)carbamate,
3-(4-methylpiperazin-1-yl)propyl (1-(6-methoxy-3,4-dihydro-2H-benzo[b][1,4]thiazin-7-yl)-6-(pyrazolo[1,5-a]pyrimidin-3-yl)-1H-pyrazolo[4,3-c]pyridin-3-yl)carbamate,
2-(piperidin-1-yl)ethyl (1-(6-methoxy-3,4-dihydro-2H-benzo[b][1,4]thiazin-7-yl)-6-(pyrazolo[1,5-a]pyrimidin-3-yl)-1H-pyrazolo[4,3-c]pyridin-3-yl)carbamate,
(R)-1-methylpyrrolidin-3-yl (1-(6-methoxy-3,4-dihydro-2H-benzo[b][1,4]thiazin-7-yl)-6-(pyrazolo[1,5-a]pyrimidin-3-yl)-1H-pyrazolo[4,3-c]pyridin-3-yl)carbamate,
(S)-1-methylpyrrolidin-3-yl (1-(6-methoxy-3,4-dihydro-2H-benzo[b][1,4]thiazin-7-yl)-6-(pyrazolo[1,5-a]pyrimidin-3-yl)-1H-pyrazolo[4,3-c]pyridin-3-yl)carbamate,
(4-(dimethylamino)tetrahydro-2H-pyran-4-yl)methyl (1-(6-methoxy-3,4-dihydro-2H-benzo[b][1,4]thiazin-7-yl)-6-(pyrazolo[1,5-a]pyrimidin-3-yl)-1H-pyrazolo[4,3-c]pyridin-3-yl)carbamate,
(R)-2-(3-methoxypyrrolidin-1-yl)ethyl (1-(6-methoxy-3,4-dihydro-2H-benzo[b][1,4]thiazin-7-yl)-6-(pyrazolo[1,5-a]pyrimidin-3-yl)-1H-pyrazolo[4,3-c]pyridin-3-yl)carbamate,
3-(1-(6-methoxy-3,4-dihydro-2H-benzo[b][1,4]thiazin-7-yl)-6-(pyrazolo[1,5-a]pyrimidin-3-yl)-1H-pyrazolo[4,3-c]pyridin-3-yl)-1,1-dimethylurea,
6-methoxy-7-(3-((2-(4-methylpiperazin-1-yl)ethyl)amino)-6-(pyrazolo[1,5-a]pyrimidin-3-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)-2H-benzo[b][1,4]thiazin-3 (4H)-one,
7-(3-((2-(dimethylamino)ethyl)amino)-6-(pyrazolo[1,5-a]pyrimidin-3-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)-6-methoxy-2H-benzo[b][1,4]thiazin-3 (4H)-one,
1-(6-methoxybenzo[d]isothiazol-5-yl)-N-(2-morpholinoethyl)-6-(pyrazolo[1,5-a]pyrimidin-3-yl)-1H-pyrazolo[4,3-c]pyridin-3-amine,
6-methoxy-7-(3-methyl-6-(pyrazolo[1,5-a]pyrimidin-3-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine,
1-(6-methoxyindolin-5-yl)-3-methyl-6-(pyrazolo[1,5-a]pyrimidin-3-yl)-1H-pyrazolo[4,3-c]pyridine,
7-methoxy-6-(3-methyl-6-(pyrazolo[1,5-a]pyrimidin-3-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)-1,2,3,4-tetrahydroquinoline,
N-(3-(dimethylamino)propyl)-1-(6-methoxy-3,4-dihydro-2H-benzo[b][1,4]oxazin-7-yl)-6-(pyrazolo[1,5-a]pyrimidin-3-yl)-1H-pyrazolo[4,3-c]pyridine-3-carboxamide,
1-(6-methoxy-3,4-dihydro-2H-benzo[b][1,4]oxazin-7-yl)-N-(1-methylazetidin-3-yl)-6-(pyrazolo[1,5-a]pyrimidin-3-yl)-1H-pyrazolo[4,3-c]pyridine-3-carboxamide,
(R)-1-(6-methoxy-3,4-dihydro-2H-benzo[b][1,4]oxazin-7-yl)-N-((4-methylmorpholin-2-yl)methyl)-6-(pyrazolo[1,5-a]pyrimidin-3-yl)-1H-pyrazolo[4,3-c]pyridine-3-carboxamide,
1-(6-methoxy-3,4-dihydro-2H-benzo[b][1,4]oxazin-7-yl)-N-(2-(4-methoxypiperidin-1-yl)ethyl)-6-(pyrazolo[1,5-a]pyrimidin-3-yl)-1H-pyrazolo[4,3-c]pyridine-3-carboxamide,
1-(6-methoxy-3,4-dihydro-2H-benzo[b][1,4]oxazin-7-yl)-N-(2-(4-(methoxymethyl)piperidin-1-yl)ethyl)-6-(pyrazolo[1,5-a]pyrimidin-3-yl)-1H-pyrazolo[4,3-c]pyridine-3-carboxamide,
N-(2-(7-oxa-2-azaspiro[3.5]nonan-2-yl)ethyl)-1-(6-methoxy-3,4-dihydro-2H-benzo[b][1,4]oxazin-7-yl)-6-(pyrazolo[1,5-a]pyrimidin-3-yl)-1H-pyrazolo[4,3-c]pyridine-3-carboxamide,
N-(2-(2-oxa-6-azaspiro[3.5]nonan-6-yl)ethyl)-1-(6-methoxy-3,4-dihydro-2H-benzo[b][1,4]oxazin-7-yl)-6-(pyrazolo[1,5-a]pyrimidin-3-yl)-1H-pyrazolo[4,3-c]pyridine-3-carboxamide,
1-(6-methoxy-3,4-dihydro-2H-benzo[b][1,4]oxazin-7-yl)-N-(2-((3aS,6aR)-1-oxotetrahydro-1H-furo[3,4-c]pyrrol-5 (3H)-yl)ethyl)-6-(pyrazolo[1,5-a]pyrimidin-3-yl)-1H-pyrazolo[4,3-c]pyridine-3-carboxamide,
1-(6-methoxy-3,4-dihydro-2H-benzo[b][1,4]oxazin-7-yl)-N-(2-(3-oxo-2-oxa-8-azaspiro[4.5]decan-8-yl)ethyl)-6-(pyrazolo[1,5-a]pyrimidin-3-yl)-1H-pyrazolo[4,3-c]pyridine-3-carboxamide,
1-(6-methoxy-3,4-dihydro-2H-benzo[b][1,4]oxazin-7-yl)-N-(2-(1-oxo-2-oxa-8-azaspiro[4.5]decan-8-yl)ethyl)-6-(pyrazolo[1,5-a]pyrimidin-3-yl)-1H-pyrazolo[4,3-c]pyridine-3-carboxamide,
N-(2-(4-(dimethylcarbamoyl)piperidin-1-yl)ethyl)-1-(6-methoxy-3,4-dihydro-2H-benzo[b][1,4]oxazin-7-yl)-6-(pyrazolo[1,5-a]pyrimidin-3-yl)-1H-pyrazolo[4,3-c]pyridine-3-carboxamide,
N1-(1-(6-methoxy-3,4-dihydro-2H-benzo[b][1,4]oxazin-7-yl)-6-(pyrazolo[1,5-a]pyrimidin-3-yl)-1H-pyrazolo[4,3-c]pyridin-3-yl)-N2,N2-dimethylethane-1,2-diamine,
1-(6-methoxy-3,4-dihydro-2H-benzo[b][1,4]oxazin-7-yl)-N-methyl-6-(pyrazolo[1,5-a]pyrimidin-3-yl)-1H-pyrazolo[4,3-c]pyridin-3-amine,
methyl (1-(6-methoxy-3,4-dihydro-2H-benzo[b][1,4]oxazin-7-yl)-6-(pyrazolo[1,5-a]pyrimidin-3-yl)-1H-pyrazolo[4,3-c]pyridin-3-yl)carbamate,
2-(dimethylamino)ethyl (1-(6-methoxy-3,4-dihydro-2H-benzo[b][1,4]oxazin-7-yl)-6-(pyrazolo[1,5-a]pyrimidin-3-yl)-1H-pyrazolo[4,3-c]pyridin-3-yl)carbamate,
2-morpholinoethyl (1-(6-methoxy-3,4-dihydro-2H-benzo[b][1,4]oxazin-7-yl)-6-(pyrazolo[1,5-a]pyrimidin-3-yl)-1H-pyrazolo[4,3-c]pyridin-3-yl)carbamate,
3-(4-methylpiperazin-1-yl)propyl (1-(6-methoxy-3,4-dihydro-2H-benzo[b][1,4]oxazin-7-yl)-6-(pyrazolo[1,5-a]pyrimidin-3-yl)-1H-pyrazolo[4,3-c]pyridin-3-yl)carbamate,
3-(dimethylamino)propyl (1-(6-methoxy-3,4-dihydro-2H-benzo[b][1,4]oxazin-7-yl)-6-(pyrazolo[1,5-a]pyrimidin-3-yl)-1H-pyrazolo[4,3-c]pyridin-3-yl)carbamate,
3-morpholinopropyl (1-(6-methoxy-3,4-dihydro-2H-benzo[b][1,4]oxazin-7-yl)-6-(pyrazolo[1,5-a]pyrimidin-3-yl)-1H-pyrazolo[4,3-c]pyridin-3-yl)carbamate,
2-(1,1-dioxidothiomorpholino)ethyl (1-(6-methoxy-3,4-dihydro-2H-benzo[b][1,4]oxazin-7-yl)-6-(pyrazolo[1,5-a]pyrimidin-3-yl)-1H-pyrazolo[4,3-c]pyridin-3-yl)carbamate,
2-(4-methylpiperazin-1-yl)ethyl (1-(6-methoxy-3,4-dihydro-2H-benzo[b][1,4]oxazin-7-yl)-6-(pyrazolo[1,5-a]pyrimidin-3-yl)-1H-pyrazolo[4,3-c]pyridin-3-yl)carbamate,
2-thiomorpholinoethyl (1-(6-methoxy-3,4-dihydro-2H-benzo[b][1,4]oxazin-7-yl)-6-(pyrazolo[1,5-a]pyrimidin-3-yl)-1H-pyrazolo[4,3-c]pyridin-3-yl)carbamate,
(S)-(4-methylmorpholin-2-yl)methyl (1-(6-methoxy-3,4-dihydro-2H-benzo[b][1,4]oxazin-7-yl)-6-(pyrazolo[1,5-a]pyrimidin-3-yl)-1H-pyrazolo[4,3-c]pyridin-3-yl)carbamate,
2-(piperidin-1-yl)ethyl (1-(6-methoxy-3,4-dihydro-2H-benzo[b][1,4]oxazin-7-yl)-6-(pyrazolo[1,5-a]pyrimidin-3-yl)-1H-pyrazolo[4,3-c]pyridin-3-yl)carbamate,
2-((2-oxotetrahydrofuran-3-yl)thio)ethyl (1-(6-methoxy-3,4-dihydro-2H-benzo[b][1,4]oxazin-7-yl)-6-(pyrazolo[1,5-a]pyrimidin-3-yl)-1H-pyrazolo[4,3-c]pyridin-3-yl)carbamate,
2-((2-oxotetrahydrofuran-3-yl)amino)ethyl (1-(6-methoxy-3,4-dihydro-2H-benzo[b][1,4]oxazin-7-yl)-6-(pyrazolo[1,5-a]pyrimidin-3-yl)-1H-pyrazolo[4,3-c]pyridin-3-yl)carbamate,
2-(dimethylamino)ethyl (1-(7-methoxy-1,2,3,4-tetrahydroquinolin-6-yl)-6-(pyrazolo[1,5-a]pyrimidin-3-yl)-1H-pyrazolo[4,3-c]pyridin-3-yl)carbamate,
1-(1-(6-methoxy-3,4-dihydro-2H-benzo[b][1,4]oxazin-7-yl)-6-(pyrazolo[1,5-a]pyrimidin-3-yl)-1H-pyrazolo[4,3-c]pyridin-3-yl)-3-(3-morpholinopropyl)urea,
6′-methoxy-5′-(3-methyl-6-(pyrazolo[1,5-a]pyrimidin-3-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)spiro[cyclopropane-1,3′-indolin]-2′-one,
5-methoxy-6-(3-((2-morpholinoethyl)amino)-6-(pyrazolo[1,5-a]pyrimidin-3-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)benzo[d]oxazol-2 (3H)-one,
N-(3-(dimethylamino)propyl)-6-(imidazo[1,2-b]pyridazin-3-yl)-1-(6-methoxy-3,4-dihydro-2H-benzo[b][1,4]oxazin-7-yl)-1H-pyrazolo[4,3-c]pyridine-3-carboxamide,
3-((3-((2-(dimethylamino)ethyl)amino)-1-(6-methoxy-3,4-dihydro-2H-benzo[b][1,4]oxazin-7-yl)-1H-pyrazolo[4,3-c]pyridin-6-yl)amino)pyrazin-2 (1H)-one,
N-(3-(dimethylamino)propyl)-1-(6-methoxy-3,4-dihydro-2H-benzo[b][1,4]oxazin-7-yl)-6-((3-oxo-3,4-dihydropyrazin-2-yl)amino)-1H-pyrazolo[4,3-c]pyridine-3-carboxamide,
N-(3-(4,4-difluoropiperidin-1-yl)propyl)-1-(6-methoxy-3,4-dihydro-2H-benzo[b][1,4]oxazin-7-yl)-6-((3-oxo-3,4-dihydropyrazin-2-yl)amino)-1H-pyrazolo[4,3-c]pyridine-3-carboxamide,
N-(2-(2,2-dimethyl-6-oxomorpholino)ethyl)-1-(6-methoxy-3,4-dihydro-2H-benzo[b][1,4]oxazin-7-yl)-6-(pyrazolo[1,5-a]pyrimidin-3-yl)-1H-pyrazolo[4,3-c]pyridine-3-carboxamide,
1-(6-(difluoromethoxy)-3,4-dihydro-2H-benzo[b][1,4]oxazin-7-yl)-N-(3-(dimethylamino)propyl)-6-(pyrazolo[1,5-a]pyrimidin-3-yl)-1H-pyrazolo[4,3-c]pyridine-3-carboxamide,
N-(2-(4-carbamoylpiperidin-1-yl)ethyl)-1-(6-methoxy-3,4-dihydro-2H-benzo[b][1,4]oxazin-7-yl)-6-(pyrazolo[1,5-a]pyrimidin-3-yl)-1H-pyrazolo[4,3-c]pyridine-3-carboxamide,
(R)—N-(2-(3-carbamoylpyrrolidin-1-yl)ethyl)-1-(6-methoxy-3,4-dihydro-2H-benzo[b][1,4]oxazin-7-yl)-6-(pyrazolo[1,5-a]pyrimidin-3-yl)-1H-pyrazolo[4,3-c]pyridine-3-carboxamide,
1-(6-methoxy-3,4-dihydro-2H-benzo[b][1,4]oxazin-7-yl)-N-(2-(7-oxo-6-oxa-2-azaspiro[3.4]octan-2-yl)ethyl)-6-(pyrazolo[1,5-a]pyrimidin-3-yl)-1H-pyrazolo[4,3-c]pyridine-3-carboxamide,
N-(2-(2-oxa-6-azaspiro[3.4]octan-6-yl)ethyl)-1-(6-methoxy-3,4-dihydro-2H-benzo[b][1,4]oxazin-7-yl)-6-(pyrazolo[1,5-a]pyrimidin-3-yl)-1H-pyrazolo[4,3-c]pyridine-3-carboxamide,
1-(6-methoxy-3,4-dihydro-2H-benzo[b][1,4]oxazin-7-yl)-N-(2-(2-methyl-6-oxomorpholino)ethyl)-6-(pyrazolo[1,5-a]pyrimidin-3-yl)-1H-pyrazolo[4,3-c]pyridine-3-carboxamide,
N-(1-(6-methoxy-3,4-dihydro-2H-benzo[b][1,4]oxazin-7-yl)-6-(pyrazolo[1,5-a]pyrimidin-3-yl)-1H-pyrazolo[4,3-c]pyridin-3-yl)-1-methylpiperidine-4-carboxamide,
N-(2-(4-(3-hydroxyoxetan-3-yl)piperidin-1-yl)ethyl)-1-(6-methoxy-3,4-dihydro-2H-benzo[b][1,4]oxazin-7-yl)-6-(pyrazolo[1,5-a]pyrimidin-3-yl)-1H-pyrazolo[4,3-c]pyridine-3-carboxamide, and
2-((2-oxotetrahydrofuran-3-yl)thio)ethyl (1-(7-methoxy-1,2,3,4-tetrahydroquinolin-6-yl)-6-(pyrazolo[1,5-a]pyrimidin-3-yl)-1H-pyrazolo[4,3-c]pyridin-3-yl)carbamate.

84 more elements

Dependencies are inferred from the claim text.

Facts

Application: 19/109,331Filed 8 Sep 2023
Priority: EP 22194839.19 Sep 2022
Published: 26 Mar 2026
Term ends: Not estimatedThe source records don’t support an estimate.

Classification15 codes

A61P 35/00
Antineoplastic agents
C07D 519/00
Heterocyclic compounds containing more than one system of two or more relevant
A61K 9/007
Galenical forms characterised by the site of application: pulmonary tract; Aromatherapy
A61K 31/519
Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim: ortho- or peri-condensed with heterocyclic rings

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