FLAP modulators
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Abstract
The present invention relates to compounds of Formula (I),
or a form thereof, wherein ring A, R1, R2, R3, R3′, L, W, and V are as defined herein, useful as FLAP modulators. The invention also relates to pharmaceutical compositions comprising compounds of Formula (I). Methods of making and using the compounds of Formula (I) are also within the scope of the invention.
13 Citations
6 Claims
-
1. A compound of Formula (I)
- View Dependent Claims (2, 3, 4, 5, 6)
-
2. The compound of claim 1, wherein
L is a bond, — - O—
, —
SO2—
NH—
, —
NH—
SO2—
, —
SO2—
, —
S—
, —
C(═
O)—
, fluoro or —
C(═
O)—
NH—
;R1 is H, bromo or CF3; R2 is H, methyl, ethyl, propyl, isopropyl, tert-butyl, cyclopropyl, cyclohexyl, pyrrolidin-1-yl, pyrrolidin-3-yl, piperidin-1-yl, piperidin-2-yl, piperidin-3-yl, piperidin-4-yl, piperazin-1-yl, tetrahydro-2H-thiopyran-4-yl, morpholin-2-yl, morpholin-4-yl, thiomorpholin-4-yl, pyrazin-2-yl, pyrimidin-2-yl, or pyrimidin-4-yl, provided R2 is not H if L is a bond, and wherein R2 is optionally substituted with hydroxyl, fluoro, amino, oxo, methyl, or —
CH2—
NH2;V is CH or N; W is CR″
or N, wherein R″
is H or F;ring A is
- O—
-
3. The compound of claim 1, wherein
L is a bond, — - O—
, —
SO2—
NH—
, —
NH—
SO2—
, —
SO2—
, —
S—
, or —
C(═
O)—
;R1 is H or CF3; R2 is H, methyl, ethyl, propyl, isopropyl, tert-butyl, cyclopropyl, cyclohexyl, pyrrolidin-1-yl, pyrrolidin-3-yl, piperidin-1-yl, piperidin-2-yl, piperidin-3-yl, piperidin-4-yl, piperazin-1-yl, tetrahydro-2H-thiopyran-4-yl, morpholin-2-yl, morpholin-4-yl, thiomorpholin-4-yl, pyrazin-2-yl, pyrimidin-2-yl, or pyrimidin-4-yl, provided R2 is not H if L is a bond, and wherein R2 is optionally substituted with hydroxyl, fluoro, amino, oxo, methyl, or —
CH2—
NH2;V is CH or N; W is CR″
or N, wherein R″
is H or F;R3 is H, and R3′
is H;or a pharmaceutically acceptable salt thereof.
- O—
-
4. The compound of claim 1, wherein the compound is selected from the group consisting of:
-
3′
-Fluoro-N-[(1S)-2-hydroxy-1-methylethyl]-4′
-(1H-pyrrolo[2,3-b]pyridin-5-yl)biphenyl-2-sulfonamide,3′
-Fluoro-N-[(1R)-2-hydroxy-1-methylethyl]-4′
-(1H-pyrrolo[2,3-b]pyridin-5-yl)biphenyl-2-sulfonamide,3′
-Fluoro-N-[(3S)-2-oxopyrrolidin-3-yl]-4′
-(1H-pyrrolo[2,3-b]pyridin-5-yl)biphenyl-2-sulfonamide,5-[2′
-(Cyclopropylsulfonyl)-3-fluorobiphenyl-4-yl]-1H-pyrrolo[2,3-b]pyridine,3′
-Fluoro-N-(2-hydroxyethyl)-4′
-(1H-pyrrolo[2,3-b]pyridin-5-yl)biphenyl-2-sulfonamide,N-tert-Butyl-3′
-fluoro-4′
-(1H-pyrrolo[2,3-b]pyridin-5-yl)biphenyl-2-sulfonamide,3′
-Fluoro-4′
-(1H-pyrrolo[2,3-b]pyridin-5-yl)biphenyl-2-sulfonamide,N-[3′
-Fluoro-4′
-(5H-pyrrolo[2,3-b]pyrazin-2-yl)biphenyl-2-yl]methanesulfonamide,3′
-Fluoro-N,N-dimethyl-4′
-(5H-pyrrolo[2,3-b]pyrazin-2-yl)biphenyl-2-sulfonamide,N-tert-Butyl-3′
-fluoro-4′
-(5H-pyrrolo[2,3-b]pyrazin-2-yl)biphenyl-2-sulfonamide,2-[3-Fluoro-2′
-(pyrrolidin-1-ylsulfonyl)biphenyl-4-yl]-5H-pyrrolo[2,3-b]pyrazine,N,N-Diethyl-3′
-fluoro-4′
-(5H-pyrrolo[2,3-b]pyrazin-2-yl)biphenyl-2-sulfonamide,2-[3-Fluoro-2′
-(piperidin-1-ylsulfonyl)biphenyl-4-yl]-5H-pyrrolo[2,3-b]pyrazine,2-[3-Fluoro-2′
-(morpholin-4-ylsulfonyl)biphenyl-4-yl]-5H-pyrrolo[2,3-b]pyrazine,3′
-Fluoro-4′
-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-N-(2,2,2-trifluoro-1-methylethyl)biphenyl-2-sulfonamide,2-[3-Fluoro-2′
-(methylsulfonyl)biphenyl-4-yl]-5H-pyrrolo[2,3-b]pyrazine,3′
-Fluoro-N-[(1R)-2-hydroxy-1-methylethyl]-4′
-(5H-pyrrol o[2,3-b]pyrazin-2-yl)biphenyl-2-sulfonamide,3′
-Fluoro-N-methyl-4′
-(5H-pyrrolo[2,3-b]pyrazin-2-yl)biphenyl-2-sulfonamide,3′
-Fluoro-N-[(1S)-2-hydroxy-1-methylethyl]-4′
-(5H-pyrrolo[2,3-b]pyrazin-2-yl)biphenyl-2-sulfonamide,1-{[3′
-Fluoro-4′
-(5H-pyrrolo[2,3-b]pyrazin-2-yl)biphenyl-2-yl]sulfonyl}piperidin-4-amine,2-{2′
-[(1, 1-Dioxidothiomorpholin-4-yl)sulfonyl]-3-fluorobiphenyl-4-yl}-5H-pyrrolo[2,3-b]pyrazine,2-[3,5′
-Difluoro-2′
-(methylsulfanyl)biphenyl-4-yl]-5H-pyrrolo[2,3-b]pyrazine,2-[2′
-(Ethylsulfanyl)-3-fluorobiphenyl-4-yl]-5H-pyrrolo[2,3-b]pyrazine,7-[3-Fluoro-2′
-(methylsulfonyl)biphenyl-4-yl]-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine,7-[3-Fluoro-2′
-(piperidin-1-ylsulfonyl)biphenyl-4-yl]-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine,4′
-(3,4-Dihydro-2H-pyrido[3,2-b][1,4]oxazin-7-yl)-3′
-fluorobiphenyl-2-sulfonamide,4′
-(3,4-Dihydro-2H-pyrido[3,2-b][1,4]oxazin-7-yl)-3′
-fluoro-N-[(1S)-2-hydroxy-1-methylethyl]biphenyl-2-sulfonamide,1-{[4′
-(3,4-Dihydro-2H-pyrido[3,2-b][1,4]oxazin-7-yl)-3′
-fluorobiphenyl-2-yl]sulfonyl}piperidin-4-amine,4′
-(3,4-Dihydro-2H-pyrido[3,2-b][1,4]oxazin-7-yl)-3′
-fluoro-N-[(1R)-2-hydroxy-1-methylethyl]biphenyl-2-sulfonamide,4′
-(3,4-Dihydro-2H-pyrido[3,2-b][1,4]oxazin-7-yl)-N,N-diethyl-3′
-fluorobiphenyl-2-sulfonamide,7-{2′
-[(1, 1-Dioxidothiomorpholin-4-yl)sulfonyl]-3-fluorobiphenyl-4-yl}-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine,N-tert-Butyl-4′
-(3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-7-yl)-3′
-fluorobiphenyl-2-sulfonamide,2-(2-Fluoro-4-{2-[(1-methylethyl)sulfanyl]-5-(trifluoromethyl)pyridin-3-yl}phenyl)-5H-pyrrolo[2,3-b]pyrazine, 2-{2-Fluoro-4-[2-(2,2,2-trifluoroethoxy)pyridin-3-yl]phenyl}-5H-pyrrolo[2,3-b]pyrazine, 2-{2-Fluoro-4-[2-(2-methylpropoxy)pyridin-3-yl]phenyl}-5H-pyrrolo[2, 3-b]pyrazine, 2-{2-Fluoro-4-[2-(1-methylethoxy)pyridin-3-yl]phenyl}-5H-pyrrolo[2,3-b]pyrazine, 2-{4-[2-(Cyclopropylmethoxy)pyridin-3-yl]-2-fluorophenyl}-5H-pyrrolo[2,3-b]pyrazine, N-tert-Butyl-3′
-fluoro-4′
-(7H-pyrrolo[2, 3-d]pyrimidin-2-yl)biphenyl-2-sulfonamide,N-tert-Butyl-3′
-fluoro-4′
-(1,8-naphthyridin-3-yl)biphenyl-2-sulfonamide,N-tert-Butyl-3′
-fluoro-4′
-quinoxalin-6-ylbiphenyl-2-sulfonamide,N-tert-Butyl-3′
-fluoro-4′
-(1H-indol-5-yl)biphenyl-2-sulfonamide,4′
-(1H-Benzimidazol-5-yl)-N-tert-butyl-3′
-fluorobiphenyl-2-sulfonamide,4′
-(1H-Benzimidazol-5-yl)-3′
-fluoro-N-methylbiphenyl-2-sulfonamide,4′
-(1,3-Benzothiazol-5-yl)-N-tert-butyl-3′
-fluorobiphenyl-2-sulfonamide,N-tert-Butyl-3′
-fluoro-4′
-(1H-pyrrolo[3,2-b]pyridin-6-yl)biphenyl-2-sulfonamide,3′
-Fluoro-N-methyl-4′
-(1H-pyrrolo[2,3-b]pyridin-5-yl)biphenyl-2-sulfonamide,N-tert-Butyl-3′
-fluoro-4′
-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyrazin-5-yl)biphenyl-2-sulfonamide,N-tert-Butyl-4′
-(2, 3-dihydro-1H-pyrrolo[2,3-b]pyridin-5-yl)-3′
-fluorobiphenyl-2-sulfonamide,N-tert-Butyl-3′
-fluoro-4′
-(3H-imidazo[4, 5-b]pyridin-6-yl)biphenyl-2-sulfonamide,4′
-(5-amino-1,3,4-thiadiazol-2-yl)-N-(tert-butyl)-3′
-fluoro-[1,1′
-biphenyl]-2-sulfonamide,(R)-4′
-(5-amino-1,3,4-thiadiazol-2-yl)-3′
-fluoro-N-(1-hydroxypropan-2-yl)-[1,1′
-biphenyl]-2-sulfonamide,4-((4′
-(5-amino-1,3,4-thiadiazol-2-yl)-3′
-fluoro-[1,1′
-biphenyl]-2-yl)sulfonyl)thiomorpholine 1,1-dioxide,N-tert-Butyl-3′
-fluoro-4′
-(1H-imidazo[4, 5-b]pyrazin-5-yl)biphenyl-2-sulfonamide,N-tert-Butyl-3′
-fluoro-4′
-[3-(hydroxymethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]biphenyl-2-sulfonamide,4′
-(7-Amino-1H-indol-5-yl)-3′
-fluoro-N-[1-(hydroxymethyl)cyclopentyl]biphenyl-2-sulfonamide,3′
-Fluoro-4′
-[3-(hydroxymethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-N-methylbiphenyl-2-sulfonamide,4′
-(7-Amino-1H-indol-5-yl)-N-tert-butyl-3′
-fluorobiphenyl-2-sulfonamide,2-[3,4′
-Difluoro-2′
-(methyl sulfonyl)biphenyl-4-yl]-5H-pyrrolo[2,3-b]pyrazine,N-[4′
-(5-Aminopyrazin-2-yl)-3′
-fluorobiphenyl-2-yl]-N-methylmethanesulfonmide,N-[3′
-Fluoro-4′
-(5H-pyrrolo[2,3-b]pyrazin-2-yl)biphenyl-2-yl]ethanesulfonamide,N-[3′
-Fluoro-4′
-(5H-pyrrolo[2,3-b]pyrazin-2-yl)biphenyl-2-yl]-N-methylmethanesulfonamide,N-[3′
-Fluoro-4′
-(5H-pyrrolo[2,3-b]pyrazin-2-yl)biphenyl-2-yl]-N-methylethanesulfonamide,N-[3′
-Fluoro-4′
-(5H-pyrrolo[2,3-b]pyrazin-2-yl)biphenyl-2-yl]-2-methylpropane-1-sulfonamide,5-[3-Fluoro-2′
-(morpholin-4-ylcarbonyl)biphenyl-4-yl]-1H-pyrrolo[2,3-b]pyridine,2-[3-Fluoro-2′
-(morpholin-4-ylcarbonyl)biphenyl-4-yl]-5H-pyrrolo[2,3-b]pyrazine,4-{[3′
-Fluoro-4′
-(1H-pyrrolo[2,3-b]pyridin-5-yl)biphenyl-2-yl]oxy}pyrimidin-2-amine,2-{[3′
-Fluoro-4′
-(1H-pyrrolo[2,3-b]pyridin-5-yl)biphenyl-2-yl]oxy}pyrimidin-4-amine,5-[3-Fluoro-2′
-(pyrimidin-2-yloxy)biphenyl-4-yl]-1H-pyrrolo[2,3-b]pyridine,5-[3-Fluoro-2′
-(pyrimidin-2-yloxy)biphenyl-4-yl]-1H-benzimidazole,6-[3-Fluoro-2′
-(pyrimidin-2-yloxy)biphenyl-4-yl]-3H-imidazo[4, 5-b]pyridine,4′
-(2-Amino-1,3-oxazol-4-yl)-N-tert-butyl-3′
-fluorobiphenyl-2-sulfonamide,4′
-(2-Amino-1,3-thiazol-4-yl)-N-tert-butyl-3′
-fluorobiphenyl-2-sulfonamide,4′
-(2-Amino-1,3-thiazol-4-yl)-N,N-diethyl-3′
-fluorobiphenyl-2-sulfonamide,4-[3-Fluoro-2′
-(pyrrolidin-1-yl sulfonyl)biphenyl-4-yl]-1,3-thiazol-2-amine,N-tert-Butyl-3′
-fluoro-4′
-(8-fluoroimidazo[1,2-a]pyridin-2-yl)biphenyl-2-sulfonamide,4′
-(5-Aminoimidazo[1,2-a]pyridin-2-yl)-N-tert-butyl-3′
-fluorobiphenyl-2-sulfonamide,2-[2′
-(tert-Butylsulfamoyl)-3-fluorobiphenyl-4-yl]imidazo[1,2-a]pyridine-6-carboxamide,2-[2′
-(tert-Butylsulfamoyl)-3-fluorobiphenyl-4-yl]imidazo[1,2-a]pyridine-6-carboxamide,N-tert-Butyl-4′
-(5-cyanoimidazo[1,2-a]pyridin-2-yl)-3′
-fluorobiphenyl-2-sulfonamide,N-tert-Butyl-4′
-(6-cyanoimidazo[1,2-a]pyridin-2-yl)-3′
-fluorobiphenyl-2-sulfonamide,N-tert-Butyl-3′
-fluoro-4′
-[6-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]biphenyl-2-sulfonamide,Ethyl 2-[2′
-(tert-butylsulfamoyl)-3-fluorobiphenyl-4-yl]imidazo[1,2-a]pyridine-5-carboxylate,N-tert-Butyl-3′
-fluoro-4′
-(5-methoxyimidazo[1,2-a]pyridin-2-yl)biphenyl-2-sulfonamide,N-tert-Butyl-3′
-fluoro-4′
-(2-oxo-2,3-dihydro-1H-indol-5-yl)biphenyl-2-sulfonamide,N-tert-Butyl-4′
-(2,4-dioxo-1,2,3,4-tetrahydroquinazolin-6-yl)-3′
-fluorobiphenyl-2-sulfonamide,4′
-(3-Amino-1H-indazol-5-yl)-N-tert-butyl-3′
-fluorobiphenyl-2-sulfonamide,5-(4′
-Bromo-2′
,3-difluorobiphenyl-4-yl)-1H-pyrrolo[2,3-b]pyridine,5-{2-Fluoro-4-[2-(morpholin-4-ylcarbonyl)pyridin-3-yl]phenyl}-1H-pyrrolo[2,3-b]pyridine, N-{3-[3-Fluoro-4-(1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl]pyridin-2-yl}-2,2-dimethylpropanamide, and 5-(2-Fluoro-4-(2-(isopropylsulfonyl)pyridine-3-yl)phenyl)-1H-pyrrolo[2,3-b]pyridine.
-
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5. A pharmaceutical composition comprising at least one compound of claim 1 and at least one pharmaceutically acceptable carrier.
-
6. The pharmaceutical composition of claim 5 comprising at least one compound of claim 4.
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2. The compound of claim 1, wherein
Specification
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Current AssigneeJanssen Pharmaceutica NV (Johnson & Johnson)
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Original AssigneeJanssen Pharmaceutica NV (Johnson & Johnson)
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InventorsBacani, Genesis M., Eccles, Wendy, Fitzgerald, Anne E., Goldberg, Steven D., Hack, Michael D., Hawryluk, Natalie A., Jones, William M., Keith, John M., Krawczuk, Paul, Lebsack, Alec D., Lee-Dutra, Alice, Liu, Jing, McClure, Kelly J., Meduna, Steven P., Pippel, Daniel J., Rosen, Mark D., Sales, Zachary S.
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Primary Examiner(s)SHAMEEM, GOLAM M
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Application NumberUS14/728,128Publication NumberTime in Patent Office980 DaysField of SearchUS Class CurrentCPC Class CodesA61P 1/00 Drugs for disorders of the ...A61P 1/04 for ulcers, gastritis or re...A61P 11/00 Drugs for disorders of the ...A61P 11/02 Nasal agents, e.g. deconges...A61P 11/06 AntiasthmaticsA61P 13/12 of the kidneysA61P 17/00 Drugs for dermatological di...A61P 19/02 for joint disorders, e.g. a...A61P 19/06 Antigout agents, e.g. antih...A61P 21/00 Drugs for disorders of the ...A61P 25/00 Drugs for disorders of the ...A61P 25/28 for treating neurodegenerat...A61P 29/00 Non-central analgesic, anti...A61P 35/00 Antineoplastic agentsA61P 35/04 specific for metastasisA61P 37/00 Drugs for immunological or ...A61P 37/08 Antiallergic agents antiast...A61P 43/00 Drugs for specific purposes...A61P 9/04 Inotropic agents, i.e. stim...A61P 9/10 for treating ischaemic or a...C07D 209/08 : with only hydrogen atoms or...C07D 213/73 : Unsubstituted amino or imin...C07D 235/10 : Radicals substituted by hal...C07D 237/20 : Nitrogen atoms nitro radica...C07D 241/20 : Nitrogen atoms nitro radica...C07D 241/26 : with nitrogen atoms directl...C07D 263/48 : Nitrogen atoms not forming ...C07D 277/62 : BenzothiazolesC07D 285/12 : 1,3,4-Thiadiazoles; Hydroge...C07D 401/04 : directly linked by a ring-m...C07D 401/10 : linked by a carbon chain co...C07D 401/12 : linked by a chain containin...C07D 401/14 : containing three or more he...C07D 403/10 : linked by a carbon chain co...C07D 403/12 : linked by a chain containin...C07D 403/14 : containing three or more he...C07D 405/12 : linked by a chain containin...C07D 405/14 : containing three or more he...C07D 409/12 : linked by a chain containin...C07D 413/10 : linked by a carbon chain co...C07D 413/12 : linked by a chain containin...C07D 413/14 : containing three or more he...C07D 417/10 : linked by a carbon chain co...C07D 471/04 : Ortho-condensed systemsC07D 487/04 : Ortho-condensed systemsC07D 487/08 : Bridged systemsC07D 491/08 : Bridged systemsC07D 491/10 : Spiro-condensed systemsC07D 491/107 : with only one oxygen atom a...C07D 495/10 : Spiro-condensed systemsC07D 498/04 : Ortho-condensed systemsC07F 5/025 : Boronic and borinic acid co...C07F 7/08 : Compounds having one or mor...C07F 7/0812 : comprising a heterocyclic ring