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US 2013/0172323 A1Published application
Pyridazinones as gpr119 agonists
AssigneeBoehringer Ingelheim International GmbH
InventorsMatthias Grauert, Remko Bakker, Steffen Breitfelder, Frank Buettner, Peter Eickelmann, Thomas Fox, Marc Grundl, Thorsten Lehmann-Lintz, Wolfgang Rist
Life of this patent
Estimating the term…
Abstract
The present invention relates to pyridazinone derivatives of general formula I, wherein the groups A, G and R1 are as defined in the application, the tautomers thereof, stereoisomers thereof, the mixtures thereof and the salts thereof, which have valuable pharmacological properties, and in particular bind to the GPR119 receptor and modulate its activity.
Claims11
A compound of formula I
- wherein:
- R1 is hydrogen, 1-4C-alkyl, 3-7C-cycloalkyl, 3-7C-cycloalkyl-1-4C-alkyl, 1-4C-alkenyl, 1-4C-alkynyl, 1-4C-alkoxy, 1-4C-alkoxy-1-4C-alkyl, wholly or partially fluorine substituted 1-4C-alkyl, or wholly or partially fluorine substituted 1-4C-alkoxy,
- A is CR2R3, O, S, or NR2, wherein R2 is a group selected from hydrogen, 1-4C-alkyl, 3-7C-cycloalkyl, 3-7C-cycloalkyl-1-4C-alkyl, 1-4C-alkenyl, 1-4C-alkynyl, 1-4C-alkoxy, 1-4C-alkoxy-1-4C-alkyl, wholly or partially fluorine substituted 1-4C-alkyl, or wholly or partially fluorine substituted 1-4C-alkoxy, or R1 and R2 together represent a bond, or a 1-7C-alkanediyl group wherein one or two —CH2— groups are optionally replaced by —O—, and R3 is hydrogen or 1-4C-alkyl, and
- G is a bicyclic system selected from the following systems G1, G2, and G3:
- wherein:
- R4 is a group optionally substituted by one to four R5 and/or R6, each independently selected from 1-4C-alkyl, 3-7C-cycloalkyl, 3-7C-cycloalkyl-1-4C-alkyl, 1-4C-alkenyl, 1-4C-alkynyl, aryl, heteroaryl, aryl-1-4C-alkyl, heteroaryl-1-4C-alkyl, heterocyclyl, and heterocyclyl-1-4C-alkyl, wherein:
- each R5 independently is hydrogen or a group optionally substituted by one to four R10 and/or R11 and/or R12, each independently selected from 1-4C-alkyl, 3-7C-cycloalkyl, 3-7C-cycloalkyl-1-4C-alkyl, 1-4C-alkenyl, 1-4C-alkynyl, aryl, heteroaryl, heterocyclyl, aryl-1-4C-alkyl, heteroaryl-1-4C-alkyl, and heterocyclyl-1-4C-alkyl, and
- each R6 independently is hydrogen or a group selected from:
- halogen, trifluoromethyl, cyano, oxo, —OR7, —N(R7)R8, —SR7, —C(O)OR7, —C(O)N(R7)R8, —S(O)2N(R7)R8, —C(O)R9, —S(O)2R9, —S(O)R9, —N(R81)C(O)OR7, —N(R81)C(O)N(R7)R8, —N(R81)S(O)2N(R7)R8, —N(R81)C(O)R9, —N(R81)S(O)2R9, and —N(R81)S(O)R9,
- wherein:
- each R7 independently is hydrogen or a group optionally substituted by one to four R10 and/or R11 and/or R12, each independently selected from 1-4C-alkyl, 3-7C-cycloalkyl, 3-7C-cycloalkyl-1-4C-alkyl, 1-4C-alkenyl, 1-4C-alkynyl, aryl, heteroaryl, heterocyclyl, aryl-1-4C-alkyl, heteroaryl-1-4C-alkyl, and heterocyclyl-1-4C-alkyl,
- each R8 independently is hydrogen or a group selected from 1-4C-alkyl and 3-7C-cycloalkyl, or R7 and R8 together represent a 1-9C-alkanediyl group wherein optionally one or two —CH2— groups may each be replaced by —O, —NR81, —S, —SQ or —SO2—, wherein each R81 independently is hydrogen or 1-4C-alkyl,
- each R9 independently is a group optionally substituted by one to four R10 and/or R11 and/or R12, each independently selected from 1-4C-alkyl, 3-7C-cycloalkyl, 3-7C-cycloalkyl-1-4C-alkyl, aryl, heteroaryl, heterocyclyl, aryl-1-4C-alkyl, heteroaryl-1-4C-alkyl, and heterocyclyl-1-4C-alkyl,
- each R10 independently is a group selected from hydrogen, 1-4C-alkyl, 3-7C-cycloalkyl, 3-7C-cycloalkyl-1-4C-alkyl, aryl, heteroaryl, heterocyclyl, aryl-1-4C-alkyl, heteroaryl-1-4C-alkyl, and heterocyclyl-1-4C-alkyl,
- each R11 independently is hydrogen or a group selected from halogen, trifluoromethyl, cyano, oxo, —OR13, —N(R13)R14, and —SR13,
- each R12 independently is hydrogen or a group selected from C(O)OR13, —C(O)N(R13)R14, —S(O)2N(R13)R14, —C(O)R15, —S(O)2R15—S(O)R15, —N(R141)C(O)OR13, —N(R141)C(O)N(R13)R14, —N(R141)S(O)2N(R13)R14, —N(R141)C(O)R15, —N(R141)S(O)2R15, and —N(R141)S(O)R15,
- each R13 independently is a group selected from hydrogen, 1-4C-alkyl, 3-7C-cycloalkyl, 3-7C-cycloalkyl-1-4C-alkyl, aryl, heteroaryl, heterocyclyl, aryl-1-4C-alkyl, heteroaryl-1-4C-alkyl, and heterocyclyl-1-4C-alkyl,
- each R14 independently is a group selected from hydrogen, 1-4C-alkyl, and 3-7C-cycloalkyl, or R13 and R14 together represent a 1-9C-alkanediyl group wherein optionally one or two —CH2— groups may each be replaced by —O, —NR141, —S, —SO, or —SO2—, wherein each R141 independently is hydrogen or 1-4C-alkyl, and
- each R15 independently is a group selected from 1-4C-alkyl, 3-7C-cycloalkyl, 3-7C-cycloalkyl-1-4C-alkyl, aryl, heteroaryl, heterocyclyl, aryl-1-4C-alkyl, heteroaryl-1-4C-alkyl, and heterocyclyl-1-4C-alkyl,
- wherein:
- aryl, on its own or as part of another group, is a carbocyclic aromatic monocyclic ring system containing 6 carbon atoms, which is optionally annelated to a second 5- or 6-membered carbocyclic aromatic, saturated or unsaturated ring system,
- heteroaryl, on its own or as part of another group, is a 5- to 12-membered, aromatic, monocyclic or condensed-polycyclic ring system containing 1 to 4 heteroatoms independently selected from N, O, and S(O)r with r=0, 1, or 2, wherein at least one of the heteroatoms is part of the aromatic ring, and
- heterocyclyl, on its own or as part of another group, a 3- to 12-membered, saturated, unsaturated or aromatic, monocyclic or condensed, bridged or spiro-polycyclic ring system containing 1 to 4 heteroatoms independently selected from N, O, and S(O)r with r=0, 1, or 2, wherein none of the heteroatoms is part of the aromatic ring,
- or a tautomer, enantiomer, or a salt thereof.
21 more elements
The compound of formula I
- wherein:
- R1 is hydrogen, 1-4C-alkyl, 3-7C-cycloalkyl, 3-7C-cycloalkyl-1-4C-alkyl, 1-4C-alkenyl, 1-4C-alkynyl, 1-4C-alkoxy, 1-4C-alkoxy-1-4C-alkyl, wholly or partially fluorine-substituted 1-4C-alkyl, or wholly or partially fluorine-substituted 1-4C-alkoxy,
- A is CR2R3, O, S, or NR2, wherein R2 is a group selected from hydrogen, 1-4C-alkyl, 3-7C-cycloalkyl, 3-7C-cycloalkyl-1-4C-alkyl, 1-4C-alkenyl, 1-4C-alkynyl, 1-4C-alkoxy, 1-4C-alkoxy-1-4C-alkyl, wholly or partially fluorine-substituted 1-4C-alkyl, or wholly or partially fluorine-substituted 1-4C-alkoxy, or R1 and R2 together represent a bond, or a 1-7C-alkanediyl group wherein one or two —CH2— groups each are optionally replaced by —O—, and R3 is hydrogen or 1-4C-alkyl, and
- G is a bicyclic system selected from the following systems G1, G2, and G3:
- wherein:
- R4 is a group optionally substituted by one to four R5 and/or R6 independently selected from 1-4C-alkyl, 3-7C-cycloalkyl, 3-7C-cycloalkyl-1-4C-alkyl, 1-4C-alkenyl, 1-4C-alkynyl, aryl, heteroaryl, aryl-1-4C-alkyl, heteroaryl-1-4C-alkyl, heterocyclyl, and heterocyclyl-1-4C-alkyl, wherein:
- each R5 independently is hydrogen or a group optionally substituted by one to four R10 and/or R11 and/or R12 independently selected from 1-4C-alkyl, 3-7C-cycloalkyl, 3-7C-cycloalkyl-1-4C-alkyl, 1-4C-alkenyl, 1-4C-alkynyl, aryl, heteroaryl, heterocyclyl, aryl-1-4C-alkyl, heteroaryl-1-4C-alkyl, and heterocyclyl-1-4C-alkyl,
- each R6 independently is hydrogen or a group selected from:
- halogen, trifluoromethyl, cyano, oxo, —OR7, —N(R7)R8, —SR7, —C(O)OR7, —C(O)N(R7)R8, S(O)2N(R7)R8, —C(O)R9, (O)2R9, (O)R9, —N(R81)C(O)OR7, —N(R81)C(O)N(R7)R8, —N(R81)S(O)2N(R7)R8, —N(R81)C(O)R9, —N(R81)S(O)2R9, and —N(R81)S(O)R9,
- wherein:
- each R7 independently is hydrogen or a group optionally substituted by one to four R10 and/or R11 and/or R12 selected from 1-4C-alkyl, 3-7C-cycloalkyl, 3-7C-cycloalkyl-1-4C-alkyl, 1-4C-alkenyl, 1-4C-alkynyl, aryl, heteroaryl, heterocyclyl, aryl-1-4C-alkyl, heteroaryl-1-4C-alkyl, and heterocyclyl-1-4C-alkyl,
- each R8 independently is hydrogen or a group selected from 1-4C-alkyl and 3-7C-cycloalkyl, or R7 and R8 together represent a 1-9C-alkanediyl group wherein one or two —CH2— groups each are optionally replaced by —O, —NR81, —S, —SO, or —SO2—, wherein each R81 independently is hydrogen or 1-4C-alkyl,
- each R9 independently is a group optionally substituted by one to four R10 and/or R11 and/or R12, each independently selected from 1-4C-alkyl, 3-7C-cycloalkyl, 3-7C-cycloalkyl-1-4C-alkyl, aryl, heteroaryl, heterocyclyl, aryl-1-4C-alkyl, heteroaryl-1-4C-alkyl, and heterocyclyl-1-4C-alkyl, wherein
- each R10 independently is a group selected from hydrogen, 1-4C-alkyl, 3-7C-cycloalkyl, 3-7C-cycloalkyl-1-4C-alkyl, aryl, heteroaryl, heterocyclyl, aryl-1-4C-alkyl, heteroaryl-1-4C-alkyl, and heterocyclyl-1-4C-alkyl,
- each R11 independently is hydrogen or a group selected from halogen, trifluoromethyl, cyano, oxo, —OR13, —N(R13)R14, and —SR13,
- each R12 independently is hydrogen or a group selected from C(O)OR13, —C(O)N(R13)R14, —S(O)2N(R13)R14, —C(O)R15, —S(O)2R15—S(O)R15, —N(R141)C(O)OR13, —N(R141)C(O)N(R13)R14, —N(R141)S(O)2N(R13)R14, —N(R141)C(O)R15, —N(R141)S(O)2R15, and —N(R141)S(O)R15, wherein
- each R13 independently is a group selected from hydrogen, 1-4C-alkyl, 3-7C-cycloalkyl, 3-7C-cycloalkyl-1-4C-alkyl, aryl, heteroaryl, heterocyclyl, aryl-1-4C-alkyl, heteroaryl-1-4C-alkyl, and heterocyclyl-1-4C-alkyl,
- each R14 independently is a group selected from hydrogen, 1-4C-alkyl and 3-7C-cycloalkyl, or R13 and R14 together represent a 1-9C-alkanediyl group wherein one or two —CH2— groups each are optionally replaced by —O, —NR141, —S, —SO, or —SO2—, wherein each R141 independently denotes is hydrogen or 1-4C-alkyl,
- each R15 independently is a group selected from 1-4C-alkyl, 3-7C-cycloalkyl, 3-7C-cycloalkyl-1-4C-alkyl, aryl, heteroaryl, heterocyclyl, aryl-1-4C-alkyl, heteroaryl-1-4C-alkyl, and heterocyclyl-1-4C-alkyl,
- wherein:
- aryl, on its own or as part of another group, is a carbocyclic aromatic monocyclic ring system containing 6 carbon atoms, which is optionally annelated to a second 5- or 6-membered carbocyclic aromatic, saturated or unsaturated ring system,
- heteroaryl, on its own or as part of another group, is a 5- to 12-membered, aromatic, monocyclic or condensed-polycyclic ring system containing 1 to 4 heteroatoms independently selected from N, O, and S(O)r with r=0, 1, or 2, wherein at least one of the heteroatoms is part of the aromatic ring, and
- heterocyclyl, on its own or as part of another group, is a 3- to 12-membered, saturated, unsaturated or aromatic, monocyclic or condensed, bridged or spiro-polycyclic ring system containing 1 to 4 heteroatoms independently selected from N, O, and S(O)r with r=0, 1, or 2, wherein none of the heteroatoms is part of the aromatic ring;
- or a tautomer, enantiomer, or a salt thereof.
21 more elements
A compound selected from the following:
- 1
- (5S)-5-methyl-6-(2-phenyl-1,3-benzoxazol-6-yl)-2,3,4,5-
- tetrahydropyridazin-3-one,
- 2
- (4S)-4-methyl-6-(2-phenyl-1,3-benzoxazol-6-yl)-2,3,4,5-
- tetrahydropyridazin-3-one,
- 3
- (5R)-5-methyl-6-(2-phenyl-1,3-benzoxazol-6-yl)-2,3,4,5-
- tetrahydropyridazin-3-one,
- 4
- (4R)-4-methyl-6-(2-phenyl-1,3-benzoxazol-6-yl)-2,3,4,5-
- tetrahydropyridazin-3-one,
- 5
- 5-(2-phenyl-1,3-benzoxazol-6-yl)-3,4-diazabicyclo[4.1.0]hept-4-en-2-one,
- 6
- 5-(7-methyl-2-phenyl-1,3-benzoxazol-6-yl)-3,4-diazabicyclo[4.1.0]hept-
- 4-en-2-one,
- 7
- 6-(2-phenyl-1,3-benzoxazol-6-yl)-4-(prop-2-en-1-yl)-2,3,4,5-
- tetrahydropyridazin-3-one,
- 8
- 6-(2-phenyl-1,3-benzoxazol-6-yl)-5-propyl-2,3,4,5-tetrahydropyridazin-3-one,
- 9
- 6-(2-phenyl-1,3-benzoxazol-6-yl)-4-propyl-2,3,4,5-tetrahydropyridazin-3-one,
- 10
- 5-(2-phenyl-1,3-benzoxazol-6-yl)-3,4-diazabicyclo[4.2.0]oct-4-en-2-one,
- 11
- 5-(4-methyl-2-phenyl-1,3-benzoxazol-6-yl)-3,4-diazabicyclo[4.1.0]hept-
- 4-en-2-one,
- 12
- 5-[2-(3-methylphenyl)-1,3-benzoxazol-6-yl]-3,4-diazabicyclo[4.1.0]hept-
- 4-en-2-one,
- 13
- 5-[2-(4-methylphenyl)-1,3-benzoxazol-6-yl]-3,4-diazabicyclo[4.1.0]hept-
- 4-en-2-one,
- 14
- 5-[2-(3,4-dimethylphenyl)-1,3-benzoxazol-6-yl]-3,4-
- diazabicyclo[4.1.0]hept-4-en-2-one,
- 15
- 5-{2-[4-(piperidin-1-ylmethyl)phenyl]-1,3-benzoxazol-6-yl}-3,4-
- diazabicyclo[4.1.0]hept-4-en-2-one,
- 16
- 6-(2-phenyl-1,3-benzoxazol-6-yl)-2,3,4,5-tetrahydropyridazin-3-one,
- 17
- 5-[2-(3-fluorophenyl)-1,3-benzoxazol-6-yl]-3,4-diazabicyclo[4.1.0]hept-
- 4-en-2-one,
- 18
- 5-[2-(4-fluorophenyl)-1,3-benzoxazol-6-yl]-3,4-diazabicyclo[4.1.0]hept-
- 4-en-2-one,
- 19
- 5-[2-(4-fluorophenyl)-1,3-benzoxazol-6-yl]-3,4-diazabicyclo[4.2.0]oct-4-
- en-2-one,
- 20
- 5-[2-(2-fluorophenyl)-1,3-benzoxazol-6-yl]-3,4-diazabicyclo[4.1.0]hept-
- 4-en-2-one,
- 21
- 4.4-dimethyl-6-(2-phenyl-1,3-benzoxazol-6-yl)-2,3,4,5-
- tetrahydropyridazin-3-one,
- 22
- 5-{2-[4-(morpholin-4-ylmethyl)phenyl]-1,3-benzoxazol-6-yl}-3,4-
- diazabicyclo[4.1.0]hept-4-en-2-one,
- 23
- tert-butyl 4-{[4-(6-{5-oxo-3,4-diazabicyclo[4.1.0]hept-2-en-2-yl}-1,3-
- benzoxazol-2-yl)phenyl]methyl}piperazine-1-carboxylate,
- 24
- (4S,5R)-4,5-dimethyl-6-[2-(5-methylthiophen-2-yl)-1,3-benzoxazol-6-yl]-
- 2,3,4,5-tetrahydropyridazin-3-one,
- 25
- (4R,5S)-4,5-dimethyl-6-(2-phenyl-1,3-benzoxazol-6-yl)-2,3,4,5-
- tetrahydropyridazin-3-one,
- 26
- (4S,5S)-4,5-dimethyl-6-(2-phenyl-1,3-benzoxazol-6-yl)-2,3,4,5-
- tetrahydropyridazin-3-one,
- 27
- (5R)-5-methoxy-6-(2-phenyl-1,3-benzoxazol-6-yl)-2,3,4,5-
- tetrahydropyridazin-3-one,
- 28
- (5S)-5-methoxy-6-(2-phenyl-1,3-benzoxazol-6-yl)-2,3,4,5-
- tetrahydropyridazin-3-one,
- 29
- 5-ethyl-6-(2-phenyl-1,3-benzoxazol-6-yl)-2,3,4,5-tetrahydropyridazin-3-one,
- 30
- (5S)-5-ethyl-6-(2-phenyl-1,3-benzoxazol-6-yl)-2,3,4,5-
- tetrahydropyridazin-3-one,
- 31
- (5R)-5-ethyl-6-(2-phenyl-1,3-benzoxazol-6-yl)-2,3,4,5-
- tetrahydropyridazin-3-one,
- 32
- 6-(2-phenyl-1,3-benzoxazol-6-yl)-5-(propan-2-yl)-2,3,4,5-
- tetrahydropyridazin-3-one,
- 33
- 6-{2-[4-(benzyloxy)phenyl]-1,3-benzoxazol-6-yl}-5-ethyl-2,3,4,5-
- tetrahydropyridazin-3-one,
- 34
- 6-{2-[3-(benzyloxy)phenyl]-1,3-benzoxazol-6-yl}-5-methyl-2,3,4,5-
- tetrahydropyridazin-3-one,
- 35
- 6-{2-[3-(benzyloxy)phenyl]-1,3-benzoxazol-6-yl}-5-ethyl-2,3,4,5-
- tetrahydropyridazin-3-one,
- 36
- 6-{2-[4-(benzyloxy)phenyl]-1,3-benzoxazol-6-yl}-5-methyl-2,3,4,5-
- tetrahydropyridazin-3-one,
- 37
- 5-ethyl-6-[2-(4-hydroxyphenyl)-1,3-benzoxazol-6-yl]-2,3,4,5-
- tetrahydropyridazin-3-one,
- 38
- 6-[2-(3-hydroxyphenyl)-1,3-benzoxazol-6-yl]-5-methyl-2,3,4,5-
- tetrahydropyridazin-3-one,
- 39
- 5-ethyl-6-[2-(3-hydroxyphenyl)-1,3-benzoxazol-6-yl]-2,3,4,5-
- tetrahydropyridazin-3-one,
- 40
- 5-ethyl-6-{2-[4-(pyrimidin-2-ylmethoxy)phenyl]-1,3-benzoxazol-6-yl}-
- 2,3,4,5-tetrahydropyridazin-3-one,
- 41
- 2-{4-[6-(4-ethyl-6-oxo-1,4,5,6-tetrahydropyridazin-3-yl)-1,3-benzoxazol-
- 2-yl]phenoxy}-N,N-dimethylacetamide,
- 42
- 5-ethyl-6-(2-{4-[(1-methyl-1H-imidazol-5-yl)methoxy]phenyl}-1,3-
- benzoxazol-6-yl)-2,3,4,5-tetrahydropyridazin-3-one,
- 43
- 2-{4-[6-(4-ethyl-6-oxo-1,4,5,6-tetrahydropyridazin-3-yl)-1,3-benzoxazol-
- 2-yl]phenoxy}-N-methylacetamide,
- 44
- 5-ethyl-6-(2-{4-[2-(4-methylpiperazin-1-yl)ethoxy]phenyl}-1,3-
- benzoxazol-6-yl)-2,3,4,5-tetrahydropyridazin-3-one,
- 45
- 5-ethyl-6-{2-[3-(pyridin-3-ylmethoxy)phenyl]-1,3-benzoxazol-6-yl}-
- 2,3,4,5-tetrahydropyridazin-3-one,
- 46
- 5-ethyl-6-{2-[4-(pyridin-4-ylmethoxy)phenyl]-1,3-benzoxazol-6-yl}-
- 2,3,4,5-tetrahydropyridazin-3-one,
- 47
- 5-ethyl-6-{2-[4-(pyridin-2-ylmethoxy)phenyl]-1,3-benzoxazol-6-yl}-
- 2,3,4,5-tetrahydropyridazin-3-one,
- 48
- 5-ethyl-6-{2-[4-(thiophen-3-ylmethoxy)phenyl]-1,3-benzoxazol-6-yl}-
- 2,3,4,5-tetrahydropyridazin-3-one,
- 49
- 5-ethyl-6-(2-{4-[2-(piperidin-1-yl)ethoxy]phenyl}-1,3-benzoxazol-6-yl)-
- 2,3,4,5-tetrahydropyridazin-3-one,
- 50
- 5-ethyl-6-[2-(4-{[3-(propan-2-yl)-1,2,4-oxadiazol-5-yl]methoxy}phenyl)-
- 1,3-benzoxazol-6-yl]-2,3,4,5-tetrahydropyridazin-3-one,
- 51
- 5-ethyl-6-{2-[4-(thiophen-2-ylmethoxy)phenyl]-1,3-benzoxazol-6-yl}-
- 2,3,4,5-tetrahydropyridazin-3-one,
- 52
- 5-ethyl-6-[2-(4-propoxyphenyl)-1,3-benzoxazol-6-yl]-2,3,4,5-
- tetrahydropyridazin-3-one,
- 53
- 6-(2-{4-[2-(azepan-1-yl)ethoxy]phenyl}-1,3-benzoxazol-6-yl)-5-ethyl-
- 2,3,4,5-tetrahydropyridazin-3-one,
- 54
- 6-{2-[4-(cyclohexylmethoxy)phenyl]-1,3-benzoxazol-6-yl}-5-ethyl-
- 2,3,4,5-tetrahydropyridazin-3-one,
- 55
- 6-(2-{4-[2-(dimethylamino)ethoxy]phenyl}-1,3-benzoxazol-6-yl)-5-ethyl-
- 2,3,4,5-tetrahydropyridazin-3-one,
- 56
- 6-{2-[4-(2-cyclohexylethoxy)phenyl]-1,3-benzoxazol-6-yl}-5-ethyl-
- 2,3,4,5-tetrahydropyridazin-3-one,
- 57
- 6-[2-(4-{2-[bis(propan-2-yl)amino]ethoxy}phenyl)-1,3-benzoxazol-6-yl]-
- 5-ethyl-2,3,4,5-tetrahydropyridazin-3-one,
- 58
- 5-ethyl-6-(2-{4-[2-(2,2,6,6-tetramethylpiperidin-1-yl)ethoxy]phenyl}-1,3-
- benzoxazol-6-yl)-2,3,4,5-tetrahydropyridazin-3-one,
- 59
- 5-ethyl-6-{2-[4-(pyrimidin-5-ylmethoxy)phenyl]-1,3-benzoxazol-6-yl}-
- 2,3,4,5-tetrahydropyridazin-3-one,
- 60
- 5-ethyl-6-{2-[4-(pyridin-3-ylmethoxy)phenyl]-1,3-benzoxazol-6-yl}-
- 2,3,4,5-tetrahydropyridazin-3-one,
- 61
- 5-ethyl-6-(2-{4-[2-oxo-2-(piperidin-1-yl)ethoxy]phenyl}-1,3-benzoxazol-
- 6-yl)-2,3,4,5-tetrahydropyridazin-3-one,
- 62
- 6-(2-{4-[3-(dimethylamino)propoxy]phenyl}-1,3-benzoxazol-6-yl)-5-
- ethyl-2,3,4,5-tetrahydropyridazin-3-one,
- 63
- 5-ethyl-6-{2-[4-(1,3-oxazol-5-ylmethoxy)phenyl]-1,3-benzoxazol-6-yl}-
- 2,3,4,5-tetrahydropyridazin-3-one,
- 64
- 5-ethyl-6-(2-{4-[2-(morpholin-4-yl)ethoxy]phenyl}-1,3-benzoxazol-6-yl)-
- 2,3,4,5-tetrahydropyridazin-3-one,
- 65
- 5-ethyl-6-{2-[3-(pyridin-2-ylmethoxy)phenyl]-1,3-benzoxazol-6-yl}-
- 2,3,4,5-tetrahydropyridazin-3-one,
- 66
- tert-butyl 2-{4-[6-(4-ethyl-6-oxo-1,4,5,6-tetrahydropyridazin-3-yl)-1,3-
- benzoxazol-2-yl]phenoxy}acetate,
- 67
- tert-butyl 4-{4-[6-(4-ethyl-6-oxo-1,4,5,6-tetrahydropyridazin-3-yl)-1,3-
- benzoxazol-2-yl]phenoxymethyl}piperidine-1-carboxylate,
- 68
- tert-butyl 4-{4-[6-(4-ethyl-6-oxo-1,4,5,6-tetrahydropyridazin-3-yl)-1,3-
- benzoxazol-2-yl]phenoxy}piperidine-1-carboxylate,
- 69
- tert-butyl 4-{3-[6-(4-methyl-6-oxo-1,4,5,6-tetrahydropyridazin-3-yl)-1,3-
- benzoxazol-2-yl]phenoxymethyl}piperidine-1-carboxylate,
- 70
- 2-{4-[6-(4-ethyl-6-oxo-1,4,5,6-tetrahydropyridazin-3-yl)-1,3-benzoxazol-
- 2-yl]phenoxy}acetic acid,
- 71
- 5-ethyl-6-{2-[4-(piperidin-4-ylmethoxy)phenyl]-1,3-benzoxazol-6-yl}-
- 2,3,4,5-tetrahydropyridazin-3-one,
- 72
- 5-ethyl-6-{2-[4-(piperidin-4-yloxy)phenyl]-1,3-benzoxazol-6-yl}-2,3,4,5-
- tetrahydropyridazin-3-one,
- 73
- 5-methyl-6-{2-[3-(piperidin-4-ylmethoxy)phenyl]-1,3-benzoxazol-6-yl}-
- 2,3,4,5-tetrahydropyridazin-3-one,
- 74
- 5-ethyl-6-(2-{4-[(1-methanesulphonylpiperidin-4-yl)methoxy]phenyl}-
- 1,3-benzoxazol-6-yl)-2,3,4,5-tetrahydropyridazin-3-one,
- 75
- 5-ethyl-6-(2-{4-[(E)-2-phenylethenyl]phenyl}-1,3-benzoxazol-6-yl)-
- 2,3,4,5-tetrahydropyridazin-3-one,
- 76
- 5-ethyl-6-{2-[4-(2-phenylethyl)phenyl]-1,3-benzoxazol-6-yl}-2,3,4,5-
- tetrahydropyridazin-3-one,
- 77
- 6-ethyl-5-(2-phenyl-1,3-benzoxazol-6-yl)-3,6-dihydro-2H-1,3,4-
- thiadiazin-2-one,
- 78
- 6-ethyl-5-(2-phenyl-1,3-benzoxazol-6-yl)-3,6-dihydro-2H-1,3,4-
- oxadiazin-2-one,
- 79
- (6R)-6-ethyl-5-(2-phenyl-1,3-benzoxazol-6-yl)-3,6-dihydro-2H-1,3,4-
- oxadiazin-2-one,
- 80
- (6S)-6-ethyl-5-(2-phenyl-1,3-benzoxazol-6-yl)-3,6-dihydro-2H-1,3,4-
- oxadiazin-2-one,
- 81
- 6-methyl-5-(2-phenyl-1,3-benzoxazol-6-yl)-3,6-dihydro-2H-1,3,4-
- oxadiazin-2-one,
- 82
- 5-methyl-6-(2-phenyl-1,3-benzoxazol-6-yl)-2,3,4,5-tetrahydropyridazin-
- 3-one,
- 83
- 6-[2-(4-methoxyphenyl)-1,3-benzoxazol-6-yl]-5-methyl-2,3,4,5-
- tetrahydropyridazin-3-one,
- 84
- 6-[2-(4-chlorophenyl)-1,3-benzoxazol-6-yl]-5-methyl-2,3,4,5-
- tetrahydropyridazin-3-one,
- 85
- 6-[2-(3-methoxyphenyl)-1,3-benzoxazol-6-yl]-5-methyl-2,3,4,5-
- tetrahydropyridazin-3-one,
- 86
- 6-[2-(2-methoxyphenyl)-1,3-benzoxazol-6-yl]-5-methyl-2,3,4,5-
- tetrahydropyridazin-3-one,
- 87
- 5-methyl-6-[2-(5-methylthiophen-2-yl)-1,3-benzoxazol-6-yl]-2,3,4,5-
- tetrahydropyridazin-3-one,
- 88
- 6-[2-(3-chlorophenyl)-1,3-benzoxazol-6-yl]-5-methyl-2,3,4,5-
- tetrahydropyridazin-3-one,
- 89
- 6-[2-(2-chlorophenyl)-1,3-benzoxazol-6-yl]-5-methyl-2,3,4,5-
- tetrahydropyridazin-3-one,
- 90
- methyl 4-[6-(4-methyl-6-oxo-1,4,5,6-tetrahydropyridazin-3-yl)-1,3-
- benzoxazol-2-yl]benzoate,
- 91
- 5-ethyl-6-[2-(2-fluoro-4-methoxyphenyl)-1,3-benzoxazol-6-yl]-2,3,4,5-
- tetrahydropyridazin-3-one,
- 92
- 6-[2-(3,4-dimethoxyphenyl)-1,3-benzoxazol-6-yl]-5-ethyl-2,3,4,5-
- tetrahydropyridazin-3-one,
- 93
- 5-ethyl-6-[2-(4-fluoro-3-methoxyphenyl)-1,3-benzoxazol-6-yl]-2,3,4,5-
- tetrahydropyridazin-3-one,
- 94
- 6-[2-(4-ethoxyphenyl)-1,3-benzoxazol-6-yl]-5-ethyl-2,3,4,5-
- tetrahydropyridazin-3-one,
- 95
- 5-ethyl-6-[2-(4-phenoxyphenyl)-1,3-benzoxazol-6-yl]-2,3,4,5-
- tetrahydropyridazin-3-one,
- 96
- 6-{2-[4-(dimethylamino)phenyl]-1,3-benzoxazol-6-yl}-5-ethyl-2,3,4,5-
- tetrahydropyridazin-3-one
- 97
- 5-ethyl-6-[2-(4-methylthiophen-2-yl)-1,3-benzoxazol-6-yl]-2,3,4,5-
- tetrahydropyridazin-3-one,
- 98
- 5-ethyl-6-[2-(3-fluoro-4-methoxyphenyl)-1,3-benzoxazol-6-yl]-2,3,4,5-
- tetrahydropyridazin-3-one,
- 99
- 5-ethyl-6-{2-[4-(propan-2-yloxy)phenyl]-1,3-benzoxazol-6-yl}-2,3,4,5-
- tetrahydropyridazin-3-one,
- 100
- 5-ethyl-6-{2-[3-(propan-2-yloxy)phenyl]-1,3-benzoxazol-6-yl}-2,3,4,5-
- tetrahydropyridazin-3-one,
- 101
- 5-ethyl-6-[2-(5-methylthiophen-2-yl)-1,3-benzoxazol-6-yl]-2,3,4,5-
- tetrahydropyridazin-3-one,
- 102
- 5-ethyl-6-[2-(3-methoxyphenyl)-1,3-benzoxazol-6-yl]-2,3,4,5-
- tetrahydropyridazin-3-one,
- 103
- 5-ethyl-6-{2-[4-(trifluoromethoxy)phenyl]-1,3-benzoxazol-6-yl}-2,3,4,5-
- tetrahydropyridazin-3-one,
- 104
- 5-ethyl-6-[2-(4-methoxyphenyl)-1,3-benzoxazol-6-yl]-2,3,4,5-
- tetrahydropyridazin-3-one,
- 105
- 5-ethyl-6-{2-[4-(oxan-4-yloxy)phenyl]-1,3-benzoxazol-6-yl}-2,3,4,5-
- tetrahydropyridazin-3-one,
- 106
- 5-methyl-6-[2-(thiophen-2-yl)-1,3-benzoxazol-6-yl]-2,3,4,5-
- tetrahydropyridazin-3-one,
- 107
- 5-methyl-6-[2-(thiophen-3-yl)-1,3-benzoxazol-6-yl]-2,3,4,5-
- tetrahydropyridazin-3-one,
- 108
- 6-[2-(furan-2-yl)-1,3-benzoxazol-6-yl]-5-methyl-2,3,4,5-
- tetrahydropyridazin-3-one,
- 109
- 6-[2-(6-aminopyridin-3-yl)-1,3-benzoxazol-6-yl]-5-methyl-2,3,4,5-
- tetrahydropyridazin-3-one,
- 110
- 5-methyl-6-[2-(pyridin-3-yl)-1,3-benzoxazol-6-yl]-2,3,4,5-
- tetrahydropyridazin-3-one,
- 111
- 6-[2-(thiophen-2-yl)-1,3-benzoxazol-6-yl]-2,3,4,5-tetrahydropyridazin-3-
- one,
- 112
- 6-[2-(furan-2-yl)-1,3-benzoxazol-6-yl]-2,3,4,5-tetrahydropyridazin-3-one,
- 113
- 5-methyl-6-[2-(thiomorpholin-4-yl)-1,3-benzoxazol-6-yl]-2,3,4,5-
- tetrahydropyridazin-3-one,
- 114
- ethyl 4-[6-(4-methyl-6-oxo-1,4,5,6-tetrahydropyridazin-3-yl)-1,3-
- benzoxazol-2-yl]piperazine-1-carboxylate,
- 115
- 5-methyl-6-[2-(piperidin-1-yl)-1,3-benzoxazol-6-yl]-2,3,4,5-
- tetrahydropyridazin-3-one,
- 116
- 5-methyl-6-[2-(morpholin-4-yl)-1,3-benzoxazol-6-yl]-2,3,4,5-
- tetrahydropyridazin-3-one,
- 117
- 5-methyl-6-[2-(piperazin-1-yl)-1,3-benzoxazol-6-yl]-2,3,4,5-
- tetrahydropyridazin-3-one,
- 118
- 6-[2-(piperidin-1-yl)-1,3-benzoxazol-6-yl]-2,3,4,5-tetrahydropyridazin-3-one,
- 119
- 6-[2-(thiomorpholin-4-yl)-1,3-benzoxazol-6-yl]-2,3,4,5-
- tetrahydropyridazin-3-one,
- 120
- 6-[2-(2,6-dichloropyridin-3-yl)-1,3-benzoxazol-6-yl]-5-methyl-2,3,4,5-
- tetrahydropyridazin-3-one,
- 121
- 6-{2-[2-chloro-6-(morpholin-4-yl)pyridin-3-yl]-1,3-benzoxazol-6-yl}-5-
- methyl-2,3,4,5-tetrahydropyridazin-3-one,
- 122
- 4-[6-(4-methyl-6-oxo-1,4,5,6-tetrahydropyridazin-3-yl)-1,3-benzoxazol-
- 2-yl]benzonitrile,
- 123
- 3-[6-(4-methyl-6-oxo-1,4,5,6-tetrahydropyridazin-3-yl)-1,3-benzoxazol-
- 2-yl]benzonitrile,
- 124
- 6-{2-[4-(aminomethyl)phenyl]-1,3-benzoxazol-6-yl}-5-methyl-2,3,4,5-
- tetrahydropyridazin-3-one,
- 125
- 6-{2-[3-(aminomethyl)phenyl]-1,3-benzoxazol-6-yl}-5-methyl-2,3,4,5-
- tetrahydropyridazin-3-one,
- 126
- (4S,5S)-4-ethyl-5-methyl-6-(2-phenyl-1,3-benzoxazol-6-yl)-2,3,4,5-
- tetrahydropyridazin-3-one,
- 127
- (4R,5S)-4-ethyl-5-methyl-6-(2-phenyl-1,3-benzoxazol-6-yl)-2,3,4,5-
- tetrahydropyridazin-3-one,
- 128
- (4S,5S)-5-methyl-6-(2-phenyl-1,3-benzoxazol-6-yl)-4-propyl-2,3,4,5-
- tetrahydropyridazin-3-one,
- 129
- (4R,5S)-5-methyl-6-(2-phenyl-1,3-benzoxazol-6-yl)-4-propyl-2,3,4,5-
- tetrahydropyridazin-3-one,
- 130
- 5-(2-phenyl-4,5,6,7-tetrahydro-1,3-benzoxazol-6-yl)-3,4-
- diazabicyclo[4.1.0]hept-4-en-2-one,
- 131
- (1R,6S)-5-[(6S)-2-phenyl-4,5,6,7-tetrahydro-1,3-benzoxazol-6-yl]-3,4-
- diazabicyclo[4.1.0]hept-4-en-2-one,
- 132
- (1R,6S)-5-[(6R)-2-phenyl-4,5,6,7-tetrahydro-1,3-benzoxazol-6-yl]-3,4-
- diazabicyclo[4.1.0]hept-4-en-2-one,
- 133
- (1S,6R)-5-[(6S)-2-phenyl-4,5,6,7-tetrahydro-1,3-benzoxazol-6-yl]-3,4-
- diazabicyclo[4.1.0]hept-4-en-2-one,
- 134
- (1S,6R)-5-[(6R)-2-phenyl-4,5,6,7-tetrahydro-1,3-benzoxazol-6-yl]-3,4-
- diazabicyclo[4.1.0]hept-4-en-2-one,
- 135
- 5-{2-phenyl-4H,5H,6H,7H-pyrido[4.3-d][1.3]oxazol-5-yl}-3,4-
- diazabicyclo[4.1.0]hept-4-en-2-one,
- 136
- 5-(2-benzyl-1,3-benzoxazol-6-yl)-3,4-diazabicyclo[4.1.0]hept-4-en-2-one,
- 137
- 5-(2-{4-[2-(morpholin-4-yl)ethoxy]phenyl}-1,3-benzoxazol-6-yl)-3,4-
- diazabicyclo[4.1.0]hept-4-en-2-one,
- 138
- 4-ethyl-6-{2-phenyl-4H,5H,6H,7H-pyrido[4.3-d][1.3]oxazol-5-yl}-
- 2,3,4,5-tetrahydropyridazin-3-one,
- 139
- 4-methyl-6-[2-(thiophen-2-yl)-1,3-benzoxazol-6-yl]-2,3,4,5-
- tetrahydropyridazin-3-one,
- 140
- 4-butyl-6-[2-(thiophen-2-yl)-1,3-benzoxazol-6-yl]-2,3,4,5-
- tetrahydropyridazin-3-one,
- 141
- 4-ethyl-6-[2-(thiophen-2-yl)-1,3-benzoxazol-6-yl]-2,3,4,5-
- tetrahydropyridazin-3-one,
- 142
- 5-methyl-6-(2-phenyl-1,3-benzoxazol-6-yl)-2,3,4,5-tetrahydro-1,2,4-
- triazin-3-one,
- 143
- 6-(2-phenyl-1,3-benzoxazol-6-yl)-2,3,4,5-tetrahydro-1,2,4-triazin-3-one,
- 144
- 5-ethyl-6-(2-phenyl-1,3-benzoxazol-6-yl)-2,3,4,5-tetrahydro-1,2,4-triazin-3-one,
- 145
- (4S,5S)-5-ethyl-4-methyl-6-(2-phenyl-1,3-benzoxazol-6-yl)-2,3,4,5-
- tetrahydropyridazin-3-one,
- 146
- (4S,5R)-5-ethyl-4-methyl-6-(2-phenyl-1,3-benzoxazol-6-yl)-2,3,4,5-
- tetrahydropyridazin-3-one,
- 147
- (4R,5R)-5-ethyl-4-methyl-6-(2-phenyl-1,3-benzoxazol-6-yl)-2,3,4,5-
- tetrahydropyridazin-3-one,
- 148
- 5-ethyl-6-(2-{3-[2-(piperidin-1-yl)ethoxy]phenyl}-1,3-benzoxazol-6-yl)-
- 2,3,4,5-tetrahydropyridazin-3-one,
- 149
- 6-(2-{3-[2-(azepan-1-yl)ethoxy]phenyl}-1,3-benzoxazol-6-yl)-5-ethyl-
- 2,3,4,5-tetrahydropyridazin-3-one,
- 150
- 5-ethyl-6-{2-[3-(pyridin-4-ylmethoxy)phenyl]-1,3-benzoxazol-6-yl}-
- 2,3,4,5-tetrahydropyridazin-3-one,
- 151
- 5-ethyl-6-(2-{3-[2-(2,2,6,6-tetramethylpiperidin-1-yl)ethoxy]phenyl}-1,3-
- benzoxazol-6-yl)-2,3,4,5-tetrahydropyridazin-3-one,
- 152
- 5-ethyl-6-(2-{3-[3-(piperidin-1-yl)propoxy]phenyl}-1,3-benzoxazol-6-
- yl)-2,3,4,5-tetrahydropyridazin-3-one,
- 153
- 1-(2-{3-[6-(4-ethyl-6-oxo-1,4,5,6-tetrahydropyridazin-3-yl)-1,3-
- benzoxazol-2-yl]phenoxy}ethyl)piperidine-4-carbonitrile,
- 154
- 6-[2-(3-{2-[bis(propan-2-yl)amino]ethoxy}phenyl)-1,3-benzoxazol-6-yl]-
- 5-ethyl-2,3,4,5-tetrahydropyridazin-3-one,
- 155
- tert-butyl 4-(2-{3-[6-(4-ethyl-6-oxo-1,4,5,6-tetrahydropyridazin-3-yl)-1,3-
- benzoxazol-2-yl]phenoxy}ethyl)piperazine-1-carboxylate,
- 156
- 6-[2-(3-{2-[bis(2-methylpropyl)amino]ethoxy}phenyl)-1,3-benzoxazol-6-
- yl]-5-ethyl-2,3,4,5-tetrahydropyridazin-3-one,
- 157
- 6-[2-(3-{2-[4-(butan-2-yl)piperazin-1-yl]ethoxy}phenyl)-1,3-benzoxazol-
- 6-yl]-5-ethyl-2,3,4,5-tetrahydropyridazin-3-one,
- 158
- 5-ethyl-6-(2-{4-[(4-methanesulphonylphenyl)methoxy]phenyl}-1,3-
- benzoxazol-6-yl)-2,3,4,5-tetrahydropyridazin-3-one,
- 159
- 5-ethyl-6-(2-{4-[2-(pyrrolidin-1-yl)ethoxy]phenyl}-1,3-benzoxazol-6-yl)-
- 2,3,4,5-tetrahydropyridazin-3-one,
- 160
- 6-[2-(4-{2-[bis(2-methylpropyl)amino]ethoxy}phenyl)-1,3-benzoxazol-6-
- yl]-5-ethyl-2,3,4,5-tetrahydropyridazin-3-one,
- 161
- 5-ethyl-6-(2-{4-[3-(piperidin-1-yl)propoxy]phenyl}-1,3-benzoxazol-6-
- yl)-2,3,4,5-tetrahydropyridazin-3-one,
- 162
- 6-(2-{4-[2-(4-acetylpiperazin-1-yl)ethoxy]phenyl}-1,3-benzoxazol-6-yl)-
- 5-ethyl-2,3,4,5-tetrahydropyridazin-3-one,
- 163
- 1-(2-{4-[6-(4-ethyl-6-oxo-1,4,5,6-tetrahydropyridazin-3-yl)-1,3-
- benzoxazol-2-yl]phenoxy}ethyl)piperidine-4-carbonitrile,
- 164
- 6-[2-(4-{2-[(1R.4S)-2-azabicyclo[2.2.1]heptan-2-yl]ethoxy}phenyl)-1,3-
- benzoxazol-6-yl]-5-ethyl-2,3,4,5-tetrahydropyridazin-3-one,
- 165
- tert-butyl 4-(2-{4-[6-(4-ethyl-6-oxo-1,4,5,6-tetrahydropyridazin-3-yl)-1,3-
- benzoxazol-2-yl]phenoxy}ethyl)piperazine-1-carboxylate,
- 166
- 6-[2-(4-{2-[4-(butan-2-yl)piperazin-1-yl]ethoxy}phenyl)-1,3-benzoxazol-
- 6-yl]-5-ethyl-2,3,4,5-tetrahydropyridazin-3-one,
- 167
- 5-ethyl-6-(2-{4-[2-(2-oxopyrrolidin-1-yl)ethoxy]phenyl}-1,3-benzoxazol-
- 6-yl)-2,3,4,5-tetrahydropyridazin-3-one,
- 168
- 5-ethyl-6-[2-(4-{2-[4-(propan-2-yl)piperazin-1-yl]ethoxy}phenyl)-1,3-
- benzoxazol-6-yl]-2,3,4,5-tetrahydropyridazin-3-one,
- 169
- (4R,5S)-6-[2-(4-{2-[bis(propan-2-yl)amino]ethoxy}phenyl)-1,3-
- benzoxazol-6-yl]-5-methyl-4-propyl-2,3,4,5-tetrahydropyridazin-3-one,
- 170
- (4S,5S)-6-[2-(4-{2-[bis(propan-2-yl)amino]ethoxy}phenyl)-1,3-
- benzoxazol-6-yl]-5-methyl-4-propyl-2,3,4,5-tetrahydropyridazin-3-one,
- 171
- (4S,5S)-5-methyl-6-{2-[4-(propan-2-yloxy)phenyl]-1,3-benzoxazol-6-yl}-
- 4-propyl-2,3,4,5-tetrahydropyridazin-3-one,
- 172
- (4S,5S)-5-methyl-6-(2-{4-[3-(piperidin-1-yl)propoxy]phenyl}-1,3-
- benzoxazol-6-yl)-4-propyl-2,3,4,5-tetrahydropyridazin-3-one,
- 173
- (4R,5R)-5-methyl-6-(2-{4-[2-(piperidin-1-yl)ethoxy]phenyl}-1,3-
- benzoxazol-6-yl)-4-propyl-2,3,4,5-tetrahydropyridazin-3-one,
- 174
- (4R,5R)-6-[2-(4-methoxyphenyl)-1,3-benzoxazol-6-yl]-5-methyl-4-
- propyl-2,3,4,5-tetrahydropyridazin-3-one,
- 175
- 5-ethyl-6-{2-[4-(propan-2-yl)phenyl]-1,3-benzoxazol-6-yl}-2,3,4,5-
- tetrahydropyridazin-3-one,
- 176
- 6-{2-[4-(cyclopentyloxy)phenyl]-1,3-benzoxazol-6-yl}-5-ethyl-2,3,4,5-
- tetrahydropyridazin-3-one,
- 177
- 5-ethyl-6-{2-[4-(morpholin-4-yl)phenyl]-1,3-benzoxazol-6-yl}-2,3,4,5-
- tetrahydropyridazin-3-one,
- 178
- (4R,5R)-5-ethyl-4-methyl-6-{2-[4-(propan-2-yloxy)phenyl]-1,3-
- benzoxazol-6-yl}-2,3,4,5-tetrahydropyridazin-3-one,
- 179
- (4R,5S)-5-ethyl-4-methyl-6-{2-[4-(propan-2-yloxy)phenyl]-1,3-
- benzoxazol-6-yl}-2,3,4,5-tetrahydropyridazin-3-one,
- 180
- 5-ethyl-6-{2-[4-(1-methoxyethyl)phenyl]-1,3-benzoxazol-6-yl}-2,3,4,5-
- tetrahydropyridazin-3-one,
- 181
- 5-ethyl-6-{2-[4-(oxolan-3-yloxy)phenyl]-1,3-benzoxazol-6-yl}-2,3,4,5-
- tetrahydropyridazin-3-one,
- 182
- (4R,5R)-6-[2-(4-fluorophenyl)-1,3-benzoxazol-6-yl]-5-methyl-4-propyl-
- 2,3,4,5-tetrahydropyridazin-3-one,
- 183
- (4R,5R)-5-methyl-4-propyl-6-[2-(thiophen-2-yl)-1,3-benzoxazol-6-yl]-
- 2,3,4,5-tetrahydropyridazin-3-one,
- 184
- (4R,5R)-5-methyl-6-[2-(5-methylthiophen-2-yl)-1,3-benzoxazol-6-yl]-4-
- propyl-2,3,4,5-tetrahydropyridazin-3-one,
- 185
- (4R,5R)-6-[2-(4-chlorophenyl)-1,3-benzoxazol-6-yl]-5-methyl-4-propyl-
- 2,3,4,5-tetrahydropyridazin-3-one,
- 186
- (4R,5R)-5-methyl-6-[2-(4-methylthiophen-2-yl)-1,3-benzoxazol-6-yl]-4-
- propyl-2,3,4,5-tetrahydropyridazin-3-one,
- 187
- (4R,5R)-5-methyl-4-propyl-6-[2-(thiophen-3-yl)-1,3-benzoxazol-6-yl]-
- 2,3,4,5-tetrahydropyridazin-3-one,
- 188
- (4R,5R)-6-[2-(furan-2-yl)-1,3-benzoxazol-6-yl]-5-methyl-4-propyl-
- 2,3,4,5-tetrahydropyridazin-3-one,
- 189
- (4R,5R)-6-[2-(2,5-dimethylfuran-3-yl)-1,3-benzoxazol-6-yl]-5-methyl-4-
- propyl-2,3,4,5-tetrahydropyridazin-3-one,
- 190
- (5R)-5-ethyl-6-[2-(4-methoxyphenyl)-1,3-benzoxazol-6-yl]-2,3,4,5-
- tetrahydropyridazin-3-one,
- 191
- (5R)-6-{2-[4-(dimethylamino)phenyl]-1,3-benzoxazol-6-yl}-5-ethyl-
- 2,3,4,5-tetrahydropyridazin-3-one,
- 192
- (5S)-5-ethyl-6-{2-[4-(propan-2-yloxy)phenyl]-1,3-benzoxazol-6-yl}-
- 2,3,4,5-tetrahydropyridazin-3-one,
- 193
- (5R)-5-ethyl-6-{2-[4-(propan-2-yloxy)phenyl]-1,3-benzoxazol-6-yl}-
- 2,3,4,5-tetrahydropyridazin-3-one,
- 194
- (5S)-5-ethyl-6-{2-[4-(oxan-4-yloxy)phenyl]-1,3-benzoxazol-6-yl}-
- 2,3,4,5-tetrahydropyridazin-3-one,
- 195
- (5R)-5-ethyl-6-{2-[4-(oxan-4-yloxy)phenyl]-1,3-benzoxazol-6-yl}-
- 2,3,4,5-tetrahydropyridazin-3-one,
- 196
- (4R,5R)-5-methyl-6-(2-phenyl-1,3-benzoxazol-6-yl)-4-propyl-2,3,4,5-
- tetrahydropyridazin-3-one,
- 197
- (4S,5S)-4-butyl-5-methyl-6-(2-phenyl-1,3-benzoxazol-6-yl)-2,3,4,5-
- tetrahydropyridazin-3-one,
- 198
- (4R,5S)-5-methyl-6-(2-phenyl-1,3-benzoxazol-6-yl)-4-(prop-2-en-1-yl)-
- 2,3,4,5-tetrahydropyridazin-3-one,
- 199
- (4R,5S)-6-{2-[4-(benzyloxy)phenyl]-1,3-benzoxazol-6-yl}-5-methyl-4-
- propyl-2,3,4,5-tetrahydropyridazin-3-one,
- 200
- (4S,5S)-6-{2-[4-(benzyloxy)phenyl]-1,3-benzoxazol-6-yl}-5-methyl-4-
- propyl-2,3,4,5-tetrahydropyridazin-3-one,
- 201
- 5-ethyl-6-(2-{3-[2-(pyrrolidin-1-yl)ethoxy]phenyl}-1,3-benzoxazol-6-yl)-
- 2,3,4,5-tetrahydropyridazin-3-one,
- 202
- (5R)-5-ethyl-6-{2-phenyl-4H,5H,6H,7H-pyrido[4.3-d][1.3]oxazol-5-yl}-
- 2,3,4,5-tetrahydropyridazin-3-one,
- 203
- (4S,5S)-6-[2-(4-hydroxyphenyl)-1,3-benzoxazol-6-yl]-5-methyl-4-propyl-
- 2,3,4,5-tetrahydropyridazin-3-one,
- 204
- 6-(2-phenyl-1,3-benzoxazol-6-yl)-2,3-dihydropyridazin-3-one,
- 205
- 6-ethyl-5-{2-phenyl-4H,5H,6H,7H-pyrido[4.3-d][1.3]oxazol-5-yl}-3,6-
- dihydro-2H-1,3,4-oxadiazin-2-one,
- 206
- (6R)-6-ethyl-5-{2-phenyl-4H,5H,6H,7H-pyrido[4.3-d][1.3]oxazol-5-yl}-
- 3,6-dihydro-2H-1,3,4-oxadiazin-2-one,
- 207
- (6S)-6-ethyl-5-{2-phenyl-4H,5H,6H,7H-pyrido[4.3-d][1.3]oxazol-5-yl}-
- 3,6-dihydro-2H-1,3,4-oxadiazin-2-one,
- 208
- (4R,5R)-5-ethyl-4-methyl-6-{2-[4-(propan-2-yloxy)phenyl]-1,3-
- benzoxazol-6-yl}-2,3,4,5-tetrahydropyridazin-3-one,
- 209
- 5-ethyl-6-(2-{4-[2-(pyrrolidin-1-yl)propoxy]phenyl}-1,3-benzoxazol-6-
- yl)-2,3,4,5-tetrahydropyridazin-3-one,
- 210
- 5-ethyl-6-[2-(4-{[1-(pyrrolidin-1-yl)propan-2-yl]oxy}phenyl)-1,3-
- benzoxazol-6-yl]-2,3,4,5-tetrahydropyridazin-3-one,
- 211
- 5-ethyl-6-{2-[4-(2-hydroxypropoxy)phenyl]-1,3-benzoxazol-6-yl}-
- 2,3,4,5-tetrahydropyridazin-3-one,
- 212
- 5-ethyl-6-(2-{4-[(2-hydroxycyclohexyl)oxy]phenyl}-1,3-benzoxazol-6-
- yl)-2,3,4,5-tetrahydropyridazin-3-one,
- 213
- 5-ethyl-6-{2-[4-(prop-2-en-1-yloxy)phenyl]-1,3-benzoxazol-6-yl}-
- 2,3,4,5-tetrahydropyridazin-3-one,
- 214
- 5-ethyl-6-{2-[4-(2-methoxyethoxy)phenyl]-1,3-benzoxazol-6-yl}-2,3,4,5-
- tetrahydropyridazin-3-one,
- 215
- 5-ethyl-6-[2-(4-{2-[ethyl(propan-2-yl)amino]ethoxy}phenyl)-1,3-
- benzoxazol-6-yl]-2,3,4,5-tetrahydropyridazin-3-one,
- 216
- 6-(2-{3-[2-(2,6-dimethylmorpholin-4-yl)ethoxy]phenyl}-1,3-benzoxazol-
- 6-yl)-5-ethyl-2,3,4,5-tetrahydropyridazin-3-one,
- 217
- 5-ethyl-6-[2-(3-{2-[methyl(propan-2-yl)amino]ethoxy}phenyl)-1,3-
- benzoxazol-6-yl]-2,3,4,5-tetrahydropyridazin-3-one,
- 218
- 5-ethyl-6-[2-(3-{2-[ethyl(propan-2-yl)amino]ethoxy}phenyl)-1,3-
- benzoxazol-6-yl]-2,3,4,5-tetrahydropyridazin-3-one,
- 219
- 5-ethyl-6-[2-(4-{2-[methyl(propan-2-yl)amino]ethoxy}phenyl)-1,3-
- benzoxazol-6-yl]-2,3,4,5-tetrahydropyridazin-3-one,
- 220
- 6-(2-{4-[2-(2,6-dimethylmorpholin-4-yl)ethoxy]phenyl}-1,3-benzoxazol-
- 6-yl)-5-ethyl-2,3,4,5-tetrahydropyridazin-3-one,
- 221
- 5-ethyl-6-[2-(4-{[1-(morpholin-4-yl)propan-2-yl]oxy}phenyl)-1,3-
- benzoxazol-6-yl]-2,3,4,5-tetrahydropyridazin-3-one,
- 222
- 6-(2-{4-[2-(diethylamino)ethoxy]phenyl}-1,3-benzoxazol-6-yl)-5-ethyl-
- 2,3,4,5-tetrahydropyridazin-3-one,
- 223
- (4S,5S)-6-[2-(4-{2-[(2R,6S)-2,6-dimethylmorpholin-4-
- yl]ethoxy}phenyl)-1,3-benzoxazol-6-yl]-5-methyl-4-propyl-2,3,4,5-
- tetrahydropyridazin-3-one,
- 224
- 6-[2-(4-{[(1R,2R)-2-(diethylamino)cyclohexyl]oxy}phenyl)-1,3-
- benzoxazol-6-yl]-5-ethyl-2,3,4,5-tetrahydropyridazin-3-one,
- 225
- 5-ethyl-6-[2-(4-{[(1R,2R)-2-(piperidin-1-yl)cyclopentyl]oxy}phenyl)-1,3-
- benzoxazol-6-yl]-2,3,4,5-tetrahydropyridazin-3-one,
- 226
- tert-butyl (2S)-2-{4-[6-(4-ethyl-6-oxo-1,4,5,6-tetrahydropyridazin-3-yl)-
- 1,3-benzoxazol-2-yl]phenoxymethyl}pyrrolidine-1-carboxylate,
- 227
- tert-butyl (2R)-2-{4-[6-(4-ethyl-6-oxo-1,4,5,6-tetrahydropyridazin-3-yl)-
- 1,3-benzoxazol-2-yl]phenoxymethyl}pyrrolidine-1-carboxylate,
- 228
- 5-ethyl-6-[2-(4-{[2-methyl-1-(pyrrolidin-1-yl)propan-2-yl]oxy}phenyl)-
- 1,3-benzoxazol-6-yl]-2,3,4,5-tetrahydropyridazin-3-one,
- 229
- 5-ethyl-6-(2-{4-[2-methyl-2-(pyrrolidin-1-yl)propoxy]phenyl}-1,3-
- benzoxazol-6-yl)-2,3,4,5-tetrahydropyridazin-3-one,
- 230
- 5-ethyl-6-[2-(3-{[1-(piperidin-1-yl)propan-2-yl]oxy}phenyl)-1,3-
- benzoxazol-6-yl]-2,3,4,5-tetrahydropyridazin-3-one,
- 231
- 5-ethyl-6-[2-(4-{[2-methyl-1-(morpholin-4-yl)propan-2-yl]oxy}phenyl)-
- 1,3-benzoxazol-6-yl]-2,3,4,5-tetrahydropyridazin-3-one,
- 232
- 5-ethyl-6-(2-{4-[2-methyl-2-(morpholin-4-yl)propoxy]phenyl}-1,3-
- benzoxazol-6-yl)-2,3,4,5-tetrahydropyridazin-3-one,
- 233
- 5-ethyl-6-(2-{4-[(1-methylpiperidin-2-yl)methoxy]phenyl}-1,3-
- benzoxazol-6-yl)-2,3,4,5-tetrahydropyridazin-3-one,
- 234
- 5-ethyl-6-(2-{4-[(1-methylazepan-2-yl)oxy]phenyl}-1,3-benzoxazol-6-
- yl)-2,3,4,5-tetrahydropyridazin-3-one,
- 235
- (5R)-5-ethyl-6-[2-(4-{[1-(piperidin-1-yl)propan-2-yl]oxy}phenyl)-1,3-
- benzoxazol-6-yl]-2,3,4,5-tetrahydropyridazin-3-one,
- 236
- (5S)-5-ethyl-6-(2-{4-[2-(piperidin-1-yl)propoxy]phenyl}-1,3-benzoxazol-
- 6-yl)-2,3,4,5-tetrahydropyridazin-3-one,
- 237
- (5R)-5-ethyl-6-(2-{4-[2-(piperidin-1-yl)propoxy]phenyl}-1,3-benzoxazol-
- 6-yl)-2,3,4,5-tetrahydropyridazin-3-one,
- 238
- 5-ethyl-6-(2-{4-[(2S)-pyrrolidin-2-ylmethoxy]phenyl}-1,3-benzoxazol-6-
- yl)-2,3,4,5-tetrahydropyridazin-3-one,
- 239
- 5-ethyl-6-(2-{4-[(2R)-pyrrolidin-2-ylmethoxy]phenyl}-1,3-benzoxazol-6-
- yl)-2,3,4,5-tetrahydropyridazin-3-one,
- 240
- 5-ethyl-6-[2-(4-{[(2S)-1-(propan-2-yl)pyrrolidin-2-yl]methoxy}phenyl)-
- 1,3-benzoxazol-6-yl]-2,3,4,5-tetrahydropyridazin-3-one,
- 241
- 5-ethyl-6-[2-(4-{[(2R)-1-(propan-2-yl)pyrrolidin-2-yl]methoxy}phenyl)-
- 1,3-benzoxazol-6-yl]-2,3,4,5-tetrahydropyridazin-3-one,
- 242
- 5-ethyl-6-[2-(4-{[(2S)-1-methylpyrrolidin-2-yl]methoxy}phenyl)-1,3-
- benzoxazol-6-yl]-2,3,4,5-tetrahydropyridazin-3-one,
- 243
- 5-ethyl-6-(2-{4-[2-(4-methylpiperidin-1-yl)ethoxy]phenyl}-1,3-
- benzoxazol-6-yl)-2,3,4,5-tetrahydropyridazin-3-one,
- 244
- 5-ethyl-6-(2-{4-[2-(4-propylpiperidin-1-yl)ethoxy]phenyl}-1,3-
- benzoxazol-6-yl)-2,3,4,5-tetrahydropyridazin-3-one,
- 245
- 6-{2-[4-(2-{3-azaspiro[5.5]undecan-3-yl}ethoxy)phenyl]-1,3-benzoxazol-
- 6-yl}-5-ethyl-2,3,4,5-tetrahydropyridazin-3-one,
- 246
- 6-[2-(4-{2-[(2R,6S)-2,6-dimethylmorpholin-4-yl]ethoxy}phenyl)-1,3-
- benzoxazol-6-yl]-5-ethyl-2,3,4,5-tetrahydropyridazin-3-one,
- 247
- 5-ethyl-6-(2-{4-[2-(thiomorpholin-4-yl)ethoxy]phenyl}-1,3-benzoxazol-
- 6-yl)-2,3,4,5-tetrahydropyridazin-3-one,
- 248
- 5-ethyl-6-(2-{4-[2-(4-fluoropiperidin-1-yl)ethoxy]phenyl}-1,3-
- benzoxazol-6-yl)-2,3,4,5-tetrahydropyridazin-3-one,
- 249
- 5-ethyl-6-[2-(4-{2-[propan-2-yl(propyl)amino]ethoxy}phenyl)-1,3-
- benzoxazol-6-yl]-2,3,4,5-tetrahydropyridazin-3-one,
- 250
- 6-[2-(4-{2-[(2R,5R)-2,5-dimethylpyrrolidin-1-yl]ethoxy}phenyl)-1,3-
- benzoxazol-6-yl]-5-ethyl-2,3,4,5-tetrahydropyridazin-3-one,
- 251
- 5-ethyl-6-(2-{4-[(1-hydroxypropan-2-yl)oxy]phenyl}-1,3-benzoxazol-6-
- yl)-2,3,4,5-tetrahydropyridazin-3-one,
- 252
- (4R,5R)-5-methyl-6-[2-(1-methyl-1H-pyrrol-2-yl)-1,3-benzoxazol-6-yl]-
- 4-propyl-2,3,4,5-tetrahydropyridazin-3-one,
- 253
- (4R,5R)-6-(2-cyclopropyl-1,3-benzoxazol-6-yl)-5-methyl-4-propyl-
- 2,3,4,5-tetrahydropyridazin-3-one,
- 254
- methyl 3-[6-(4-methyl-6-oxo-1,6-dihydropyridazin-3-yl)-1,3-benzoxazol-
- 2-yl]benzoate,
- 255
- 4-[6-(4-methyl-6-oxo-1,6-dihydropyridazin-3-yl)-1,3-benzoxazol-2-
- yl]benzoic acid,
- 256
- 5-methyl-6-[2-(thiophen-2-yl)-1,3-benzoxazol-6-yl]-2,3-
- dihydropyridazin-3-one,
- 257
- 6-[2-(thiophen-2-yl)-1,3-benzoxazol-6-yl]-2,3-dihydropyridazin-3-one,
- 258
- (5S)-6-[2-(4-{2-[bis(propan-2-yl)amino]ethoxy}phenyl)-1,3-benzoxazol-
- 6-yl]-5-ethyl-2,3,4,5-tetrahydropyridazin-3-one,
- 259
- (5R)-6-[2-(4-{2-[bis(propan-2-yl)amino]ethoxy}phenyl)-1,3-benzoxazol-
- 6-yl]-5-ethyl-2,3,4,5-tetrahydropyridazin-3-one, and
- 260
- (4R,5R)-5-methyl-6-{2-[4-(propan-2-yloxy)phenyl]-1,3-benzoxazol-6-
- yl}-4-propyl-2,3,4,5-tetrahydropyridazin-3-one,
- or a tautomer, enantiomer, or a salt thereof.
766 more elements
Dependencies are inferred from the claim text.