JP2017505327A5

JP2017505327A5 -

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Publication number: JP2017505327A5
Authority: JP; Japan
Prior art keywords: oxy; pyridin; trifluoromethyl; alkyl; quinolin
Prior art date: 2015-02-04
Legal status : Granted

Application number

JP2016550611A

Other languages

English (en)

Japanese (ja)

Other versions

JP6532474B2 (ja

JP2017505327A (ja

Filing date

2015-02-04

Publication date

2018-03-15

2015-02-04 Application filed filed Critical

2015-02-04 Priority claimed from PCT/US2015/014380 external-priority patent/WO2015119998A1/en

2017-02-16 Publication of JP2017505327A publication Critical patent/JP2017505327A/ja

2018-03-15 Publication of JP2017505327A5 publication Critical patent/JP2017505327A5/ja

2019-06-19 Application granted granted Critical

2019-06-19 Publication of JP6532474B2 publication Critical patent/JP6532474B2/ja

Status Expired - Fee Related legal-status Critical Current

2035-02-04 Anticipated expiration legal-status Critical

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125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 188
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 184
-1 halo-C 1 -C 6 -alkyl Chemical group 0.000 claims 144
229910052739 hydrogen Inorganic materials 0.000 claims 89
239000001257 hydrogen Substances 0.000 claims 89
150000002431 hydrogen Chemical class 0.000 claims 75
229910052736 halogen Inorganic materials 0.000 claims 59
150000002367 halogens Chemical class 0.000 claims 59
125000001424 substituent group Chemical group 0.000 claims 50
125000004093 cyano group Chemical group *C#N 0.000 claims 37
208000002193 Pain Diseases 0.000 claims 35
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 33
150000001875 compounds Chemical class 0.000 claims 29
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 25
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 25
125000000623 heterocyclic group Chemical group 0.000 claims 25
125000004043 oxo group Chemical group O=* 0.000 claims 24
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 23
125000003118 aryl group Chemical group 0.000 claims 23
125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 21
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 19
125000005843 halogen group Chemical group 0.000 claims 19
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 18
229910052757 nitrogen Inorganic materials 0.000 claims 18
229910052799 carbon Inorganic materials 0.000 claims 17
125000000753 cycloalkyl group Chemical group 0.000 claims 17
ZEXKKIXCRDTKBF-UHFFFAOYSA-N quinoline-2-carboxamide Chemical compound C1=CC=CC2=NC(C(=O)N)=CC=C21 ZEXKKIXCRDTKBF-UHFFFAOYSA-N 0.000 claims 17
125000002911 monocyclic heterocycle group Chemical group 0.000 claims 15
125000000217 alkyl group Chemical group 0.000 claims 13
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 12
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 12
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 12
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 11
125000004433 nitrogen atom Chemical group N* 0.000 claims 11
125000002618 bicyclic heterocycle group Chemical group 0.000 claims 10
125000000169 tricyclic heterocycle group Chemical group 0.000 claims 10
125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 9
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 8
125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 7
125000001072 heteroaryl group Chemical group 0.000 claims 7
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 7
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 6
LKIPNCBMOXYGPF-UHFFFAOYSA-N 6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinoline-2-carbaldehyde Chemical compound FC(C=1C=CC(=NC=1)OC=1C=C2C=CC(=NC2=CC=1)C=O)(F)F LKIPNCBMOXYGPF-UHFFFAOYSA-N 0.000 claims 6
208000006820 Arthralgia Diseases 0.000 claims 6
125000000392 cycloalkenyl group Chemical group 0.000 claims 6
125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims 6
238000000034 method Methods 0.000 claims 6
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 6
125000004844 (C1-C6) alkoxyimino group Chemical group 0.000 claims 5
150000001408 amides Chemical class 0.000 claims 5
150000003857 carboxamides Chemical class 0.000 claims 5
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 5
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 5
150000002148 esters Chemical class 0.000 claims 5
WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 claims 5
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 5
125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 5
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 5
150000003839 salts Chemical class 0.000 claims 5
HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims 4
208000035475 disorder Diseases 0.000 claims 4
208000004296 neuralgia Diseases 0.000 claims 4
208000021722 neuropathic pain Diseases 0.000 claims 4
RFIOZSIHFNEKFF-UHFFFAOYSA-M piperazine-1-carboxylate Chemical compound [O-]C(=O)N1CCNCC1 RFIOZSIHFNEKFF-UHFFFAOYSA-M 0.000 claims 4
239000011734 sodium Substances 0.000 claims 4
208000011580 syndromic disease Diseases 0.000 claims 4
241000124008 Mammalia Species 0.000 claims 3
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 3
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 3
BRYCUMKDWMEGMK-UHFFFAOYSA-N piperazine-2-carboxamide Chemical compound NC(=O)C1CNCCN1 BRYCUMKDWMEGMK-UHFFFAOYSA-N 0.000 claims 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 2
125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 claims 2
206010002383 Angina Pectoris Diseases 0.000 claims 2
206010058019 Cancer Pain Diseases 0.000 claims 2
206010064012 Central pain syndrome Diseases 0.000 claims 2
208000006561 Cluster Headache Diseases 0.000 claims 2
208000023890 Complex Regional Pain Syndromes Diseases 0.000 claims 2
208000032131 Diabetic Neuropathies Diseases 0.000 claims 2
208000005171 Dysmenorrhea Diseases 0.000 claims 2
201000009273 Endometriosis Diseases 0.000 claims 2
208000001640 Fibromyalgia Diseases 0.000 claims 2
206010019233 Headaches Diseases 0.000 claims 2
208000007514 Herpes zoster Diseases 0.000 claims 2
208000004454 Hyperalgesia Diseases 0.000 claims 2
208000035154 Hyperesthesia Diseases 0.000 claims 2
206010065390 Inflammatory pain Diseases 0.000 claims 2
208000000913 Kidney Calculi Diseases 0.000 claims 2
206010027476 Metastases Diseases 0.000 claims 2
208000019695 Migraine disease Diseases 0.000 claims 2
206010029148 Nephrolithiasis Diseases 0.000 claims 2
208000001294 Nociceptive Pain Diseases 0.000 claims 2
208000018737 Parkinson disease Diseases 0.000 claims 2
206010034620 Peripheral sensory neuropathy Diseases 0.000 claims 2
208000004983 Phantom Limb Diseases 0.000 claims 2
206010056238 Phantom pain Diseases 0.000 claims 2
206010036376 Postherpetic Neuralgia Diseases 0.000 claims 2
208000004550 Postoperative Pain Diseases 0.000 claims 2
208000027520 Somatoform disease Diseases 0.000 claims 2
208000006011 Stroke Diseases 0.000 claims 2
206010042496 Sunburn Diseases 0.000 claims 2
206010043269 Tension headache Diseases 0.000 claims 2
208000008548 Tension-Type Headache Diseases 0.000 claims 2
206010046798 Uterine leiomyoma Diseases 0.000 claims 2
102000016913 Voltage-Gated Sodium Channels Human genes 0.000 claims 2
108010053752 Voltage-Gated Sodium Channels Proteins 0.000 claims 2
FWLFRXVPNVBXGR-CQSZACIVSA-N [(3R)-3-fluoropyrrolidin-1-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound F[C@H]1CN(CC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F FWLFRXVPNVBXGR-CQSZACIVSA-N 0.000 claims 2
125000005119 alkyl cycloalkyl group Chemical group 0.000 claims 2
125000002619 bicyclic group Chemical group 0.000 claims 2
210000000988 bone and bone Anatomy 0.000 claims 2
208000003295 carpal tunnel syndrome Diseases 0.000 claims 2
201000001883 cholelithiasis Diseases 0.000 claims 2
208000022371 chronic pain syndrome Diseases 0.000 claims 2
208000018912 cluster headache syndrome Diseases 0.000 claims 2
206010009887 colitis Diseases 0.000 claims 2
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
125000006317 cyclopropyl amino group Chemical group 0.000 claims 2
239000003937 drug carrier Substances 0.000 claims 2
230000000694 effects Effects 0.000 claims 2
201000011384 erythromelalgia Diseases 0.000 claims 2
208000001130 gallstones Diseases 0.000 claims 2
231100000869 headache Toxicity 0.000 claims 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
125000004356 hydroxy functional group Chemical group O* 0.000 claims 2
208000024765 knee pain Diseases 0.000 claims 2
201000010260 leiomyoma Diseases 0.000 claims 2
230000009401 metastasis Effects 0.000 claims 2
206010027599 migraine Diseases 0.000 claims 2
201000006417 multiple sclerosis Diseases 0.000 claims 2
201000008482 osteoarthritis Diseases 0.000 claims 2
229910052760 oxygen Inorganic materials 0.000 claims 2
208000027753 pain disease Diseases 0.000 claims 2
230000001314 paroxysmal effect Effects 0.000 claims 2
239000008194 pharmaceutical composition Substances 0.000 claims 2
DWXLVZSMXXCSMJ-UHFFFAOYSA-N piperazine-1-sulfonamide Chemical compound NS(=O)(=O)N1CCNCC1 DWXLVZSMXXCSMJ-UHFFFAOYSA-N 0.000 claims 2
206010039073 rheumatoid arthritis Diseases 0.000 claims 2
201000005572 sensory peripheral neuropathy Diseases 0.000 claims 2
208000020431 spinal cord injury Diseases 0.000 claims 2
238000006467 substitution reaction Methods 0.000 claims 2
238000001356 surgical procedure Methods 0.000 claims 2
210000001738 temporomandibular joint Anatomy 0.000 claims 2
208000004371 toothache Diseases 0.000 claims 2
206010044652 trigeminal neuralgia Diseases 0.000 claims 2
208000009935 visceral pain Diseases 0.000 claims 2
BTJACOBEUSJEEM-UHFFFAOYSA-N (2-hydroxy-6-azaspiro[3.4]octan-6-yl)-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound OC1CC2(C1)CN(CC2)C(=O)C2=NC1=CC=C(C=C1C=C2)OC2=NC=C(C=C2)C(F)(F)F BTJACOBEUSJEEM-UHFFFAOYSA-N 0.000 claims 1
CEHHVXZVNFTBAS-UHFFFAOYSA-N (2-hydroxy-7-azaspiro[3.5]nonan-7-yl)-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound OC1CC2(C1)CCN(CC2)C(=O)C2=NC1=CC=C(C=C1C=C2)OC2=NC=C(C=C2)C(F)(F)F CEHHVXZVNFTBAS-UHFFFAOYSA-N 0.000 claims 1
YSWMLBYOFNTORG-UHFFFAOYSA-N (3,3-difluoro-4-hydroxypiperidin-1-yl)-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound FC1(CN(CCC1O)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F)F YSWMLBYOFNTORG-UHFFFAOYSA-N 0.000 claims 1
SJPWYPFQPIGEAJ-UHFFFAOYSA-N (3,3-difluoroazetidin-1-yl)-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound FC1(CN(C1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F)F SJPWYPFQPIGEAJ-UHFFFAOYSA-N 0.000 claims 1
BQACDOTXYLXGRX-UHFFFAOYSA-N (3,3-difluoropiperidin-1-yl)-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound FC1(CN(CCC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F)F BQACDOTXYLXGRX-UHFFFAOYSA-N 0.000 claims 1
FJHABEQXOGLWAA-UHFFFAOYSA-N (3,3-difluoropyrrolidin-1-yl)-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound FC1(CN(CC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F)F FJHABEQXOGLWAA-UHFFFAOYSA-N 0.000 claims 1
LSLAQWMJZSJQKS-UHFFFAOYSA-N (3,3-dimethylpyrrolidin-1-yl)-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound CC1(CN(CC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F)C LSLAQWMJZSJQKS-UHFFFAOYSA-N 0.000 claims 1
LFYFHYZDVFQHTH-UHFFFAOYSA-N (3,4-difluoropyrrolidin-1-yl)-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound FC1CN(CC1F)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F LFYFHYZDVFQHTH-UHFFFAOYSA-N 0.000 claims 1
SIPFNLUMBAVCLD-UHFFFAOYSA-N (3,5-dimethylpiperazin-1-yl)-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound CC1CN(CC(N1)C)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F SIPFNLUMBAVCLD-UHFFFAOYSA-N 0.000 claims 1
ZIJRMCGLMZBVMG-UHFFFAOYSA-N (3-aminoazetidin-1-yl)-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound NC1CN(C1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F ZIJRMCGLMZBVMG-UHFFFAOYSA-N 0.000 claims 1
BIGHKHAOUKBPBK-UHFFFAOYSA-N (3-aminoazetidin-1-yl)-[6-[6-(trifluoromethyl)pyridin-3-yl]oxyquinolin-2-yl]methanone Chemical compound NC1CN(C1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC=1C=NC(=CC1)C(F)(F)F BIGHKHAOUKBPBK-UHFFFAOYSA-N 0.000 claims 1
UGTQZSTXWDRYAP-UHFFFAOYSA-N (3-fluoro-4-hydroxypyrrolidin-1-yl)-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound FC1CN(CC1O)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F UGTQZSTXWDRYAP-UHFFFAOYSA-N 0.000 claims 1
KNBPVYBCUKTPKI-UHFFFAOYSA-N (3-fluoroazetidin-1-yl)-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound FC1CN(C1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F KNBPVYBCUKTPKI-UHFFFAOYSA-N 0.000 claims 1
FWLFRXVPNVBXGR-UHFFFAOYSA-N (3-fluoropyrrolidin-1-yl)-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound FC1CN(CC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F FWLFRXVPNVBXGR-UHFFFAOYSA-N 0.000 claims 1
GBCYQDYWDUJCNT-UHFFFAOYSA-N (3-hydroxy-3-methylazetidin-1-yl)-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound OC1(CN(C1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F)C GBCYQDYWDUJCNT-UHFFFAOYSA-N 0.000 claims 1
UWIUGCDRGBFUAS-UHFFFAOYSA-N (3-hydroxy-7-azaspiro[3.5]nonan-7-yl)-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound OC1CCC12CCN(CC2)C(=O)C2=NC1=CC=C(C=C1C=C2)OC2=NC=C(C=C2)C(F)(F)F UWIUGCDRGBFUAS-UHFFFAOYSA-N 0.000 claims 1
ZREKKWPDZCRCBE-UHFFFAOYSA-N (3-hydroxyazetidin-1-yl)-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound OC1CN(C1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F ZREKKWPDZCRCBE-UHFFFAOYSA-N 0.000 claims 1
OOJQMRZQVVQZJI-UHFFFAOYSA-N (3-imidazol-1-ylazetidin-1-yl)-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound N1(C=NC=C1)C1CN(C1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F OOJQMRZQVVQZJI-UHFFFAOYSA-N 0.000 claims 1
IUCUSJUHEPWLLR-UHFFFAOYSA-N (3-methoxyazetidin-1-yl)-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound COC1CN(C1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F IUCUSJUHEPWLLR-UHFFFAOYSA-N 0.000 claims 1
KAEJAMZBFMAFRO-UHFFFAOYSA-N (3-methyl-3-phenoxyazetidin-1-yl)-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound CC1(CN(C1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F)OC1=CC=CC=C1 KAEJAMZBFMAFRO-UHFFFAOYSA-N 0.000 claims 1
XYCSIKBESLTOLI-UHFFFAOYSA-N (3-methylsulfonylazetidin-1-yl)-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound CS(=O)(=O)C1CN(C1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F XYCSIKBESLTOLI-UHFFFAOYSA-N 0.000 claims 1
YROOGHUYUGVPAQ-UHFFFAOYSA-N (3-methylsulfonylazetidin-1-yl)-[6-[6-(trifluoromethyl)pyridin-3-yl]oxyquinolin-2-yl]methanone Chemical compound CS(=O)(=O)C1CN(C1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC=1C=NC(=CC1)C(F)(F)F YROOGHUYUGVPAQ-UHFFFAOYSA-N 0.000 claims 1
UDWNGAZVVZLPKX-UHFFFAOYSA-N (3-methylsulfonylpyrrolidin-1-yl)-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound CS(=O)(=O)C1CN(CC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F UDWNGAZVVZLPKX-UHFFFAOYSA-N 0.000 claims 1
KZWVIMUVSQUGHR-UHFFFAOYSA-N (3-morpholin-4-ylazetidin-1-yl)-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound N1(CCOCC1)C1CN(C1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F KZWVIMUVSQUGHR-UHFFFAOYSA-N 0.000 claims 1
MFNSUPZPTBSSQB-UHFFFAOYSA-N (3-morpholin-4-ylazetidin-1-yl)-[6-[6-(trifluoromethyl)pyridin-3-yl]oxyquinolin-2-yl]methanone Chemical compound N1(CCOCC1)C1CN(C1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC=1C=NC(=CC1)C(F)(F)F MFNSUPZPTBSSQB-UHFFFAOYSA-N 0.000 claims 1
YZNQEVAANSONJW-UHFFFAOYSA-N (3-morpholin-4-ylpyrrolidin-1-yl)-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound N1(CCOCC1)C1CN(CC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F YZNQEVAANSONJW-UHFFFAOYSA-N 0.000 claims 1
RLQAIQVYEQZBIL-UHFFFAOYSA-N (3-phenoxyazetidin-1-yl)-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound O(C1=CC=CC=C1)C1CN(C1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F RLQAIQVYEQZBIL-UHFFFAOYSA-N 0.000 claims 1
IBJHCHXBHWSBPS-UHFFFAOYSA-N (3-piperazin-1-ylazetidin-1-yl)-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound N1(CCNCC1)C1CN(C1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F IBJHCHXBHWSBPS-UHFFFAOYSA-N 0.000 claims 1
PZWDWHPWGNSKMV-UHFFFAOYSA-N (3-pyridin-3-ylazetidin-1-yl)-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound N1=CC(=CC=C1)C1CN(C1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F PZWDWHPWGNSKMV-UHFFFAOYSA-N 0.000 claims 1
RAEMQBPGBLQRJY-CJNGLKHVSA-N (3aR,6aR)-5-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinoline-2-carbonyl]-1,2,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrol-3-one Chemical compound FC(F)(F)C1=CN=C(OC2=CC=C3N=C(C=CC3=C2)C(=O)N2C[C@H]3CNC(=O)[C@H]3C2)C=C1 RAEMQBPGBLQRJY-CJNGLKHVSA-N 0.000 claims 1
QTXFNFAEPQLDAZ-UHFFFAOYSA-N (4,4-difluoro-3-hydroxypiperidin-1-yl)-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound FC1(C(CN(CC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F)O)F QTXFNFAEPQLDAZ-UHFFFAOYSA-N 0.000 claims 1
KRPABQOWYBMFBX-UHFFFAOYSA-N (4,4-difluoropiperidin-1-yl)-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound FC1(CCN(CC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F)F KRPABQOWYBMFBX-UHFFFAOYSA-N 0.000 claims 1
SJWKYMBEDPTROM-UHFFFAOYSA-M (4,4-dimethylpiperazin-4-ium-1-yl)-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone iodide Chemical compound [I-].C[N+]1(CCN(CC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F)C SJWKYMBEDPTROM-UHFFFAOYSA-M 0.000 claims 1
GRMQYLXIWBGZPB-UHFFFAOYSA-N (4-cyclobutylpiperazin-1-yl)-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound C1(CCC1)N1CCN(CC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F GRMQYLXIWBGZPB-UHFFFAOYSA-N 0.000 claims 1
FXIOYXBLZAGOHT-UHFFFAOYSA-N (4-cyclohexylpiperazin-1-yl)-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound C1(CCCCC1)N1CCN(CC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F FXIOYXBLZAGOHT-UHFFFAOYSA-N 0.000 claims 1
VAUVOXYVYWZDJU-UHFFFAOYSA-N (4-cyclopropylpiperazin-1-yl)-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound C1(CC1)N1CCN(CC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F VAUVOXYVYWZDJU-UHFFFAOYSA-N 0.000 claims 1
CUTAOELLLYPMMD-UHFFFAOYSA-N (4-ethylpiperazin-1-yl)-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound C(C)N1CCN(CC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F CUTAOELLLYPMMD-UHFFFAOYSA-N 0.000 claims 1
LUWPGLSYMNTTAE-UHFFFAOYSA-N (4-fluoropiperidin-1-yl)-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound FC1CCN(CC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F LUWPGLSYMNTTAE-UHFFFAOYSA-N 0.000 claims 1
HMRJPLDKLJOOLQ-UHFFFAOYSA-N (4-hydroxy-4-methylpiperidin-1-yl)-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound OC1(CCN(CC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F)C HMRJPLDKLJOOLQ-UHFFFAOYSA-N 0.000 claims 1
CCGGFONFHUTDCP-UHFFFAOYSA-N (4-hydroxyazepan-1-yl)-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound OC1CCN(CCC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F CCGGFONFHUTDCP-UHFFFAOYSA-N 0.000 claims 1
CERBTCPPZKOLBE-UHFFFAOYSA-N (4-hydroxypiperidin-1-yl)-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound OC1CCN(CC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F CERBTCPPZKOLBE-UHFFFAOYSA-N 0.000 claims 1
HDVADOYYGYXCJT-UHFFFAOYSA-N (4-methoxyiminopiperidin-1-yl)-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound CON=C1CCN(CC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F HDVADOYYGYXCJT-UHFFFAOYSA-N 0.000 claims 1
JXWDNLSXMYYLAM-UHFFFAOYSA-N (4-methyl-1,4-diazepan-1-yl)-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound CN1CCN(CCC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F JXWDNLSXMYYLAM-UHFFFAOYSA-N 0.000 claims 1
WTYDLIVNXOKESA-UHFFFAOYSA-N (4-methylpiperazin-1-yl)-(6-pyridin-2-yloxyquinolin-2-yl)methanone Chemical compound CN1CCN(CC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=CC=C1 WTYDLIVNXOKESA-UHFFFAOYSA-N 0.000 claims 1
KHMCBUOHWOTOQE-UHFFFAOYSA-N (4-methylpiperazin-1-yl)-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound CN1CCN(CC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F KHMCBUOHWOTOQE-UHFFFAOYSA-N 0.000 claims 1
ZCIHKHAMWORQLA-UHFFFAOYSA-N (4-methylsulfonylpiperazin-1-yl)-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound CS(=O)(=O)N1CCN(CC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F ZCIHKHAMWORQLA-UHFFFAOYSA-N 0.000 claims 1
GTSRUQHDGIMSEK-UHFFFAOYSA-N (4-methylsulfonylpiperidin-1-yl)-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound CS(=O)(=O)C1CCN(CC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F GTSRUQHDGIMSEK-UHFFFAOYSA-N 0.000 claims 1
FFWDDSSNXRZFBF-UHFFFAOYSA-N (4-morpholin-4-ylpiperidin-1-yl)-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound N1(CCOCC1)C1CCN(CC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F FFWDDSSNXRZFBF-UHFFFAOYSA-N 0.000 claims 1
DTMWNAVSRQDWBC-UHFFFAOYSA-N (4-morpholin-4-ylpiperidin-1-yl)-[6-[6-(trifluoromethyl)pyridin-3-yl]oxyquinolin-2-yl]methanone Chemical compound N1(CCOCC1)C1CCN(CC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC=1C=NC(=CC1)C(F)(F)F DTMWNAVSRQDWBC-UHFFFAOYSA-N 0.000 claims 1
CRJPEVPBPILWCE-UHFFFAOYSA-N (4-morpholin-4-ylsulfonylpiperazin-1-yl)-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound N1(CCOCC1)S(=O)(=O)N1CCN(CC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F CRJPEVPBPILWCE-UHFFFAOYSA-N 0.000 claims 1
XJHPJCQUYQSCNH-UHFFFAOYSA-N (4-phenylpiperazin-1-yl)-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound C1(=CC=CC=C1)N1CCN(CC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F XJHPJCQUYQSCNH-UHFFFAOYSA-N 0.000 claims 1
LUIDZMYIVNIUTM-UHFFFAOYSA-N (4-piperidin-1-ylsulfonylpiperazin-1-yl)-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound N1(CCCCC1)S(=O)(=O)N1CCN(CC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F LUIDZMYIVNIUTM-UHFFFAOYSA-N 0.000 claims 1
ARFWMLHGXYAFDZ-UHFFFAOYSA-N (4-propan-2-ylpiperazin-1-yl)-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound C(C)(C)N1CCN(CC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F ARFWMLHGXYAFDZ-UHFFFAOYSA-N 0.000 claims 1
GFVNNUACWLPMDE-UHFFFAOYSA-N (4-propan-2-ylsulfonylpiperazin-1-yl)-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound C(C)(C)S(=O)(=O)N1CCN(CC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F GFVNNUACWLPMDE-UHFFFAOYSA-N 0.000 claims 1
YGXFDUYUTBMMDZ-UHFFFAOYSA-N (4-pyrazin-2-ylpiperazin-1-yl)-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound N1=C(C=NC=C1)N1CCN(CC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F YGXFDUYUTBMMDZ-UHFFFAOYSA-N 0.000 claims 1
PLXHNCLRUJUHGD-UHFFFAOYSA-N (4-pyridazin-3-ylpiperazin-1-yl)-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound N1=NC(=CC=C1)N1CCN(CC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F PLXHNCLRUJUHGD-UHFFFAOYSA-N 0.000 claims 1
SPIRMFMMMOFAFD-UHFFFAOYSA-N (4-pyridin-3-ylpiperazin-1-yl)-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound N1=CC(=CC=C1)N1CCN(CC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F SPIRMFMMMOFAFD-UHFFFAOYSA-N 0.000 claims 1
RAIPERDXFBPZKH-UHFFFAOYSA-N (4-pyridin-3-ylsulfonylpiperazin-1-yl)-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound N1=CC(=CC=C1)S(=O)(=O)N1CCN(CC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F RAIPERDXFBPZKH-UHFFFAOYSA-N 0.000 claims 1
DRKIMXRKULJOEF-UHFFFAOYSA-N (4-pyrimidin-2-ylpiperazin-1-yl)-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound N1=C(N=CC=C1)N1CCN(CC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F DRKIMXRKULJOEF-UHFFFAOYSA-N 0.000 claims 1
VDDYIZOWNZUUSI-UHFFFAOYSA-N (4-tert-butylpiperazin-1-yl)-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound C(C)(C)(C)N1CCN(CC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F VDDYIZOWNZUUSI-UHFFFAOYSA-N 0.000 claims 1
BZRWQRSJTGOBHC-UHFFFAOYSA-N (6,6-difluoro-1,4-diazepan-1-yl)-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound FC1(CNCCN(C1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F)F BZRWQRSJTGOBHC-UHFFFAOYSA-N 0.000 claims 1
OQCPWENMNHUYRW-UHFFFAOYSA-N (6-fluoro-1,4-diazepan-1-yl)-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound FC1CNCCN(C1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F OQCPWENMNHUYRW-UHFFFAOYSA-N 0.000 claims 1
ONUFZWLUZQKUOB-UHFFFAOYSA-N (6-hydroxy-1,4-diazepan-1-yl)-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound OC1CNCCN(C1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F ONUFZWLUZQKUOB-UHFFFAOYSA-N 0.000 claims 1
ZRLYLBAQCLWFQE-IRXDYDNUSA-N (8S,9aS)-8-hydroxy-2-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinoline-2-carbonyl]-3,4,7,8,9,9a-hexahydro-1H-pyrrolo[1,2-a][1,4]diazepin-5-one Chemical compound O[C@H]1C[C@@H]2N(C(CCN(C2)C(=O)C2=NC3=CC=C(C=C3C=C2)OC2=NC=C(C=C2)C(F)(F)F)=O)C1 ZRLYLBAQCLWFQE-IRXDYDNUSA-N 0.000 claims 1
TTZXDLQCUFCAMB-OAHLLOKOSA-N (8aR)-7-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinoline-2-carbonyl]-5,6,8,8a-tetrahydro-1H-[1,3]oxazolo[3,4-a]pyrazin-3-one Chemical compound FC(C=1C=CC(=NC1)OC=1C=C2C=CC(=NC2=CC1)C(=O)N1C[C@H]2N(CC1)C(OC2)=O)(F)F TTZXDLQCUFCAMB-OAHLLOKOSA-N 0.000 claims 1
AZNWLKFIQDFAQV-INIZCTEOSA-N (8aS)-2-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinoline-2-carbonyl]-1,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazin-4-one Chemical compound FC(C=1C=CC(=NC1)OC=1C=C2C=CC(=NC2=CC1)C(=O)N1C[C@H]2N(C(C1)=O)CCC2)(F)F AZNWLKFIQDFAQV-INIZCTEOSA-N 0.000 claims 1
CSYZLTDYRMWRDD-UHFFFAOYSA-N 1,3-diazinan-1-yl-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound N1(CNCCC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F CSYZLTDYRMWRDD-UHFFFAOYSA-N 0.000 claims 1
FEDZSKDIJDSSHJ-UHFFFAOYSA-N 1,4-diazepan-1-yl-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound N1(CCNCCC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F FEDZSKDIJDSSHJ-UHFFFAOYSA-N 0.000 claims 1
JCIBFZGYMJKCPM-UHFFFAOYSA-N 1,4-dioxa-7-azaspiro[4.4]nonan-7-yl-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound O1CCOC12CN(CC2)C(=O)C2=NC1=CC=C(C=C1C=C2)OC2=NC=C(C=C2)C(F)(F)F JCIBFZGYMJKCPM-UHFFFAOYSA-N 0.000 claims 1
GJZRDXHRKJFPCJ-UHFFFAOYSA-N 1,4-dioxa-8-azaspiro[4.5]decan-8-yl-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound O1CCOC12CCN(CC2)C(=O)C2=NC1=CC=C(C=C1C=C2)OC2=NC=C(C=C2)C(F)(F)F GJZRDXHRKJFPCJ-UHFFFAOYSA-N 0.000 claims 1
UMBHUIWMPXJMPB-UHFFFAOYSA-N 1-(3-methoxyphenyl)-4-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinoline-2-carbonyl]piperazin-2-one Chemical compound COC=1C=C(C=CC1)N1C(CN(CC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F)=O UMBHUIWMPXJMPB-UHFFFAOYSA-N 0.000 claims 1
BCDJRDDKTSCYGF-UHFFFAOYSA-N 1-[1-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinoline-2-carbonyl]azetidin-3-yl]ethanone Chemical compound FC(C=1C=CC(=NC1)OC=1C=C2C=CC(=NC2=CC1)C(=O)N1CC(C1)C(C)=O)(F)F BCDJRDDKTSCYGF-UHFFFAOYSA-N 0.000 claims 1
BVCBGQASRGPDLU-UHFFFAOYSA-N 1-[4-[2-(piperazine-1-carbonyl)quinolin-6-yl]oxyphenyl]ethanone Chemical compound N1(CCNCC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=CC=C(C=C1)C(C)=O BVCBGQASRGPDLU-UHFFFAOYSA-N 0.000 claims 1
LPISIPDPQIAHID-UHFFFAOYSA-N 1-[4-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinoline-2-carbonyl]piperazin-1-yl]ethanone Chemical compound FC(C=1C=CC(=NC1)OC=1C=C2C=CC(=NC2=CC1)C(=O)N1CCN(CC1)C(C)=O)(F)F LPISIPDPQIAHID-UHFFFAOYSA-N 0.000 claims 1
VMCFXQPRPSFGDA-UHFFFAOYSA-N 1-[6-[2-(piperazine-1-carbonyl)quinolin-6-yl]oxypyridin-3-yl]ethanone Chemical compound N1(CCNCC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=CC=C(C=N1)C(C)=O VMCFXQPRPSFGDA-UHFFFAOYSA-N 0.000 claims 1
BKRMBLUWRKKSDZ-UHFFFAOYSA-N 1-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinoline-2-carbonyl]-2,3,4,7,8,8a-hexahydropyrrolo[1,2-a]pyrimidin-6-one Chemical compound FC(C=1C=CC(=NC1)OC=1C=C2C=CC(=NC2=CC1)C(=O)N1C2N(CCC1)C(CC2)=O)(F)F BKRMBLUWRKKSDZ-UHFFFAOYSA-N 0.000 claims 1
JXSSFUUDDCRPIK-UHFFFAOYSA-N 1-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinoline-2-carbonyl]azetidin-3-one Chemical compound FC(C=1C=CC(=NC1)OC=1C=C2C=CC(=NC2=CC1)C(=O)N1CC(C1)=O)(F)F JXSSFUUDDCRPIK-UHFFFAOYSA-N 0.000 claims 1
ZLJXSOXSCVXYDD-UHFFFAOYSA-N 1-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinoline-2-carbonyl]azetidine-3-carbonitrile Chemical compound FC(C=1C=CC(=NC1)OC=1C=C2C=CC(=NC2=CC1)C(=O)N1CC(C1)C#N)(F)F ZLJXSOXSCVXYDD-UHFFFAOYSA-N 0.000 claims 1
AKOCWANAWXSDQP-UHFFFAOYSA-N 1-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinoline-2-carbonyl]piperidin-4-one Chemical compound FC(C=1C=CC(=NC1)OC=1C=C2C=CC(=NC2=CC1)C(=O)N1CCC(CC1)=O)(F)F AKOCWANAWXSDQP-UHFFFAOYSA-N 0.000 claims 1
CPTINAWEICFQJI-UHFFFAOYSA-N 1-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinoline-2-carbonyl]piperidine-4-carbonitrile Chemical compound FC(C=1C=CC(=NC1)OC=1C=C2C=CC(=NC2=CC1)C(=O)N1CCC(CC1)C#N)(F)F CPTINAWEICFQJI-UHFFFAOYSA-N 0.000 claims 1
PXTNPCJIZUAIDB-UHFFFAOYSA-N 1-methyl-4-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinoline-2-carbonyl]piperazin-2-one Chemical compound CN1C(CN(CC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F)=O PXTNPCJIZUAIDB-UHFFFAOYSA-N 0.000 claims 1
FGMXVWFBGMMCLI-UHFFFAOYSA-N 2,5-dihydropyrrol-1-yl-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound N1(CC=CC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F FGMXVWFBGMMCLI-UHFFFAOYSA-N 0.000 claims 1
DYVRJIBLYNFXNG-UHFFFAOYSA-N 2,5-dihydropyrrol-1-yl-[6-[6-(trifluoromethyl)pyridin-3-yl]oxyquinolin-2-yl]methanone Chemical compound N1(CC=CC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC=1C=NC(=CC1)C(F)(F)F DYVRJIBLYNFXNG-UHFFFAOYSA-N 0.000 claims 1
XPCLEYSCJYFUCR-UHFFFAOYSA-N 2,6-diazaspiro[3.3]heptan-2-yl-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound C1N(CC12CNC2)C(=O)C2=NC1=CC=C(C=C1C=C2)OC2=NC=C(C=C2)C(F)(F)F XPCLEYSCJYFUCR-UHFFFAOYSA-N 0.000 claims 1
LLLQSNRFSNRBES-UHFFFAOYSA-N 2,7-diazaspiro[3.5]nonan-2-yl-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound C1N(CC12CCNCC2)C(=O)C2=NC1=CC=C(C=C1C=C2)OC2=NC=C(C=C2)C(F)(F)F LLLQSNRFSNRBES-UHFFFAOYSA-N 0.000 claims 1
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VTHLRWFYLISRMY-IAMHBRQHSA-N [(1R,4R,6R)-6-(hydroxymethyl)-2-azabicyclo[2.2.1]heptan-2-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound OC[C@@H]1C[C@H]2CN([C@@H]1C2)C(=O)C2=NC1=CC=C(C=C1C=C2)OC2=NC=C(C=C2)C(F)(F)F VTHLRWFYLISRMY-IAMHBRQHSA-N 0.000 claims 1
VTHLRWFYLISRMY-WAWZGNHOSA-N [(1R,4R,6S)-6-(hydroxymethyl)-2-azabicyclo[2.2.1]heptan-2-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound OC[C@H]1C[C@H]2CN([C@@H]1C2)C(=O)C2=NC1=CC=C(C=C1C=C2)OC2=NC=C(C=C2)C(F)(F)F VTHLRWFYLISRMY-WAWZGNHOSA-N 0.000 claims 1
YKGJRLADRAPYEL-GJZGRUSLSA-N [(1S,4S)-2,5-diazabicyclo[2.2.1]heptan-2-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound [C@@H]12N(C[C@@H](NC1)C2)C(=O)C2=NC1=CC=C(C=C1C=C2)OC2=NC=C(C=C2)C(F)(F)F YKGJRLADRAPYEL-GJZGRUSLSA-N 0.000 claims 1
BFGDKCTUHKHGHR-SCLBCKFNSA-N [(1S,5S)-3,6-diazabicyclo[3.2.0]heptan-3-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound [C@@H]12CN(C[C@H]2NC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F BFGDKCTUHKHGHR-SCLBCKFNSA-N 0.000 claims 1
NTJUSWRVFLTWST-QGZVFWFLSA-N [(2R)-2-(difluoromethyl)piperazin-1-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound FC([C@@H]1N(CCNC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F)F NTJUSWRVFLTWST-QGZVFWFLSA-N 0.000 claims 1
WGHXVZSGWIYPCP-OAHLLOKOSA-N [(2R)-2-(hydroxymethyl)piperazin-1-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound OC[C@@H]1N(CCNC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F WGHXVZSGWIYPCP-OAHLLOKOSA-N 0.000 claims 1
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DPICSRQZHLHQOI-YJYMSZOUSA-N [(2R,3R)-3-ethyl-2-(hydroxymethyl)azetidin-1-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound C(C)[C@H]1[C@@H](N(C1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F)CO DPICSRQZHLHQOI-YJYMSZOUSA-N 0.000 claims 1
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URKQWTIIFRZTLT-UZUQRXQVSA-N [(2R,4R)-2-(2,5-difluorophenyl)-4-fluoropyrrolidin-1-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound FC1=C(C=C(C=C1)F)[C@@H]1N(C[C@@H](C1)F)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F URKQWTIIFRZTLT-UZUQRXQVSA-N 0.000 claims 1
URKQWTIIFRZTLT-GAJHUEQPSA-N [(2R,4S)-2-(2,5-difluorophenyl)-4-fluoropyrrolidin-1-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound FC1=C(C=C(C=C1)F)[C@@H]1N(C[C@H](C1)F)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F URKQWTIIFRZTLT-GAJHUEQPSA-N 0.000 claims 1
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QPPRPXMHZCGEDA-LSDHHAIUSA-N [(2R,4S)-4-fluoro-2-(hydroxymethyl)pyrrolidin-1-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound F[C@H]1C[C@@H](N(C1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F)CO QPPRPXMHZCGEDA-LSDHHAIUSA-N 0.000 claims 1
WGHXVZSGWIYPCP-HNNXBMFYSA-N [(2S)-2-(hydroxymethyl)piperazin-1-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound OC[C@H]1N(CCNC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F WGHXVZSGWIYPCP-HNNXBMFYSA-N 0.000 claims 1
UXSACQGSTLEKBE-HNNXBMFYSA-N [(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound OC[C@H]1N(CCC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F UXSACQGSTLEKBE-HNNXBMFYSA-N 0.000 claims 1
IOMLFLAHQOXFIU-AWEZNQCLSA-N [(2S)-4,4-difluoro-2-(hydroxymethyl)pyrrolidin-1-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound FC1(C[C@H](N(C1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F)CO)F IOMLFLAHQOXFIU-AWEZNQCLSA-N 0.000 claims 1
JMLHMSXQNJBYJG-LSDHHAIUSA-N [(2S,4R)-4-hydroxy-2-(hydroxymethyl)pyrrolidin-1-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound O[C@@H]1C[C@H](N(C1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F)CO JMLHMSXQNJBYJG-LSDHHAIUSA-N 0.000 claims 1
QPPRPXMHZCGEDA-GJZGRUSLSA-N [(2S,4S)-4-fluoro-2-(hydroxymethyl)pyrrolidin-1-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound F[C@H]1C[C@H](N(C1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F)CO QPPRPXMHZCGEDA-GJZGRUSLSA-N 0.000 claims 1
PLCWFJNNLUWLTR-OAHLLOKOSA-N [(3R)-3-(hydroxymethyl)piperazin-1-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound OC[C@H]1CN(CCN1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F PLCWFJNNLUWLTR-OAHLLOKOSA-N 0.000 claims 1
FTJAPQFLCMDRST-CQSZACIVSA-N [(3R)-3-(hydroxymethyl)piperazin-1-yl]-[6-[6-(trifluoromethyl)pyridin-3-yl]oxyquinolin-2-yl]methanone Chemical compound OC[C@H]1CN(CCN1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC=1C=NC(=CC1)C(F)(F)F FTJAPQFLCMDRST-CQSZACIVSA-N 0.000 claims 1
BCOHYAVYZWPAHD-MRXNPFEDSA-N [(3R)-3-(methoxymethyl)piperazin-1-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound COC[C@H]1CN(CCN1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F BCOHYAVYZWPAHD-MRXNPFEDSA-N 0.000 claims 1
MXMPAEFBKRMQFZ-OAHLLOKOSA-N [(3R)-3-(methoxymethyl)piperazin-1-yl]-[6-[6-(trifluoromethyl)pyridin-3-yl]oxyquinolin-2-yl]methanone Chemical compound COC[C@H]1CN(CCN1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC=1C=NC(=CC1)C(F)(F)F MXMPAEFBKRMQFZ-OAHLLOKOSA-N 0.000 claims 1
ATRROIBIMTTXSL-MRXNPFEDSA-N [(3R)-3-ethylpiperazin-1-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound C(C)[C@@H]1CN(CCN1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F ATRROIBIMTTXSL-MRXNPFEDSA-N 0.000 claims 1
LAZIJOCRLNJLOI-OAHLLOKOSA-N [(3R)-3-ethylpiperazin-1-yl]-[6-[6-(trifluoromethyl)pyridin-3-yl]oxyquinolin-2-yl]methanone Chemical compound C(C)[C@@H]1CN(CCN1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC=1C=NC(=CC1)C(F)(F)F LAZIJOCRLNJLOI-OAHLLOKOSA-N 0.000 claims 1
CVGPTFLWNCNLTG-CYBMUJFWSA-N [(3R)-3-fluoropyrrolidin-1-yl]-[6-[5-(trifluoromethoxy)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound F[C@H]1CN(CC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)OC(F)(F)F CVGPTFLWNCNLTG-CYBMUJFWSA-N 0.000 claims 1
GJIPOROCDOMYPF-CYBMUJFWSA-N [(3R)-3-fluoropyrrolidin-1-yl]-[6-[6-(trifluoromethyl)pyridin-3-yl]oxyquinolin-2-yl]methanone Chemical compound F[C@H]1CN(CC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC=1C=NC(=CC1)C(F)(F)F GJIPOROCDOMYPF-CYBMUJFWSA-N 0.000 claims 1
CTMRVPUKKRXAHX-OAHLLOKOSA-N [(3R)-3-hydroxypiperidin-1-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound O[C@H]1CN(CCC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F CTMRVPUKKRXAHX-OAHLLOKOSA-N 0.000 claims 1
XNNRRBJEMZEYGE-CQSZACIVSA-N [(3R)-3-hydroxypyrrolidin-1-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound O[C@H]1CN(CC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F XNNRRBJEMZEYGE-CQSZACIVSA-N 0.000 claims 1
SJXKVERJOYIPFL-MRXNPFEDSA-N [(3R)-3-methoxypyrrolidin-1-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound CO[C@H]1CN(CC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F SJXKVERJOYIPFL-MRXNPFEDSA-N 0.000 claims 1
BMQCLTSPZXCHIP-CYBMUJFWSA-N [(3R)-3-methylpiperazin-1-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound C[C@@H]1CN(CCN1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F BMQCLTSPZXCHIP-CYBMUJFWSA-N 0.000 claims 1
FKRJOLGOCURNRA-CYBMUJFWSA-N [(3R)-3-methylpiperazin-1-yl]-[6-[6-(trifluoromethyl)pyridin-3-yl]oxyquinolin-2-yl]methanone Chemical compound C[C@@H]1CN(CCN1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC=1C=NC(=CC1)C(F)(F)F FKRJOLGOCURNRA-CYBMUJFWSA-N 0.000 claims 1
FPKLSYXMRIOKHK-LJQANCHMSA-N [(3R)-3-piperidin-1-ylpyrrolidin-1-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound N1(CCCCC1)[C@H]1CN(CC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F FPKLSYXMRIOKHK-LJQANCHMSA-N 0.000 claims 1
XVBZCTDRLDACGG-FQEVSTJZSA-N [(3R)-3-propan-2-ylpiperazin-1-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound C(C)(C)[C@@H]1CN(CCN1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F XVBZCTDRLDACGG-FQEVSTJZSA-N 0.000 claims 1
DOILHXAUWXGMJF-IAGOWNOFSA-N [(3R,4R)-3,4-dihydroxypyrrolidin-1-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound O[C@@H]1CN(C[C@H]1O)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F DOILHXAUWXGMJF-IAGOWNOFSA-N 0.000 claims 1
VLRHZLKUJNLZIT-CRAIPNDOSA-N [(3R,4R)-3-fluoro-4-hydroxypiperidin-1-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound F[C@@H]1CN(CC[C@H]1O)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F VLRHZLKUJNLZIT-CRAIPNDOSA-N 0.000 claims 1
KDYCKFUXRZHDSX-QZTJIDSGSA-N [(3R,4R)-3-hydroxy-4-methoxypyrrolidin-1-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound O[C@@H]1CN(C[C@H]1OC)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F KDYCKFUXRZHDSX-QZTJIDSGSA-N 0.000 claims 1
KMVMIMJOGNJQEO-QZTJIDSGSA-N [(3R,4R)-3-hydroxy-4-methylsulfonylpyrrolidin-1-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound O[C@@H]1CN(C[C@H]1S(=O)(=O)C)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F KMVMIMJOGNJQEO-QZTJIDSGSA-N 0.000 claims 1
BCUCKVQNVQRFDP-HZPDHXFCSA-N [(3R,4R)-4-amino-3-fluoropiperidin-1-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound N[C@H]1[C@@H](CN(CC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F)F BCUCKVQNVQRFDP-HZPDHXFCSA-N 0.000 claims 1
MWEQMCAEPGKADY-CRAIPNDOSA-N [(3R,4R)-4-fluoro-3-hydroxypiperidin-1-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound F[C@H]1[C@@H](CN(CC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F)O MWEQMCAEPGKADY-CRAIPNDOSA-N 0.000 claims 1
AUPWWVIZKYGGSL-ZWKOTPCHSA-N [(3R,4S)-3,4-dihydroxypiperidin-1-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound O[C@@H]1CN(CC[C@@H]1O)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F AUPWWVIZKYGGSL-ZWKOTPCHSA-N 0.000 claims 1
VLRHZLKUJNLZIT-QAPCUYQASA-N [(3R,4S)-3-fluoro-4-hydroxypiperidin-1-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound F[C@@H]1CN(CC[C@@H]1O)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F VLRHZLKUJNLZIT-QAPCUYQASA-N 0.000 claims 1
XAFWCCIFPPZXSN-MOPGFXCFSA-N [(3R,4S)-3-hydroxy-4-(methoxymethoxy)pyrrolidin-1-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound O[C@@H]1CN(C[C@@H]1OCOC)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F XAFWCCIFPPZXSN-MOPGFXCFSA-N 0.000 claims 1
MWEQMCAEPGKADY-MAUKXSAKSA-N [(3R,4S)-4-fluoro-3-hydroxypiperidin-1-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound F[C@@H]1[C@@H](CN(CC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F)O MWEQMCAEPGKADY-MAUKXSAKSA-N 0.000 claims 1
SEKDARFYRQMCLH-HUUCEWRRSA-N [(3R,5R)-3,5-dihydroxypiperidin-1-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound O[C@H]1CN(C[C@@H](C1)O)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F SEKDARFYRQMCLH-HUUCEWRRSA-N 0.000 claims 1
CPNFGXGWKUSDPX-FHLIZLRMSA-N [(3R,7S,8aR)-7-fluoro-3-methyl-3,4,6,7,8,8a-hexahydro-1H-pyrrolo[1,2-a]pyrazin-2-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound F[C@H]1C[C@H]2N(C[C@H](N(C2)C(=O)C2=NC3=CC=C(C=C3C=C2)OC2=NC=C(C=C2)C(F)(F)F)C)C1 CPNFGXGWKUSDPX-FHLIZLRMSA-N 0.000 claims 1
PKLXLDDZVFSEHH-RHSMWYFYSA-N [(3R,8aR)-7,7-difluoro-3-methyl-1,3,4,6,8,8a-hexahydropyrrolo[1,2-a]pyrazin-2-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound FC1(C[C@H]2N(C[C@H](N(C2)C(=O)C2=NC3=CC=C(C=C3C=C2)OC2=NC=C(C=C2)C(F)(F)F)C)C1)F PKLXLDDZVFSEHH-RHSMWYFYSA-N 0.000 claims 1
PLCWFJNNLUWLTR-HNNXBMFYSA-N [(3S)-3-(hydroxymethyl)piperazin-1-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound OC[C@@H]1CN(CCN1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F PLCWFJNNLUWLTR-HNNXBMFYSA-N 0.000 claims 1
FTJAPQFLCMDRST-AWEZNQCLSA-N [(3S)-3-(hydroxymethyl)piperazin-1-yl]-[6-[6-(trifluoromethyl)pyridin-3-yl]oxyquinolin-2-yl]methanone Chemical compound OC[C@@H]1CN(CCN1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC=1C=NC(=CC1)C(F)(F)F FTJAPQFLCMDRST-AWEZNQCLSA-N 0.000 claims 1
MXMPAEFBKRMQFZ-HNNXBMFYSA-N [(3S)-3-(methoxymethyl)piperazin-1-yl]-[6-[6-(trifluoromethyl)pyridin-3-yl]oxyquinolin-2-yl]methanone Chemical compound COC[C@@H]1CN(CCN1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC=1C=NC(=CC1)C(F)(F)F MXMPAEFBKRMQFZ-HNNXBMFYSA-N 0.000 claims 1
ATRROIBIMTTXSL-INIZCTEOSA-N [(3S)-3-ethylpiperazin-1-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound C(C)[C@H]1CN(CCN1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F ATRROIBIMTTXSL-INIZCTEOSA-N 0.000 claims 1
LAZIJOCRLNJLOI-HNNXBMFYSA-N [(3S)-3-ethylpiperazin-1-yl]-[6-[6-(trifluoromethyl)pyridin-3-yl]oxyquinolin-2-yl]methanone Chemical compound C(C)[C@H]1CN(CCN1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC=1C=NC(=CC1)C(F)(F)F LAZIJOCRLNJLOI-HNNXBMFYSA-N 0.000 claims 1
FWLFRXVPNVBXGR-AWEZNQCLSA-N [(3S)-3-fluoropyrrolidin-1-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound F[C@@H]1CN(CC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F FWLFRXVPNVBXGR-AWEZNQCLSA-N 0.000 claims 1
GJIPOROCDOMYPF-ZDUSSCGKSA-N [(3S)-3-fluoropyrrolidin-1-yl]-[6-[6-(trifluoromethyl)pyridin-3-yl]oxyquinolin-2-yl]methanone Chemical compound F[C@@H]1CN(CC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC=1C=NC(=CC1)C(F)(F)F GJIPOROCDOMYPF-ZDUSSCGKSA-N 0.000 claims 1
CTMRVPUKKRXAHX-HNNXBMFYSA-N [(3S)-3-hydroxypiperidin-1-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound O[C@@H]1CN(CCC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F CTMRVPUKKRXAHX-HNNXBMFYSA-N 0.000 claims 1
XNNRRBJEMZEYGE-AWEZNQCLSA-N [(3S)-3-hydroxypyrrolidin-1-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound O[C@@H]1CN(CC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F XNNRRBJEMZEYGE-AWEZNQCLSA-N 0.000 claims 1
SJXKVERJOYIPFL-INIZCTEOSA-N [(3S)-3-methoxypyrrolidin-1-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound CO[C@@H]1CN(CC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F SJXKVERJOYIPFL-INIZCTEOSA-N 0.000 claims 1
BMQCLTSPZXCHIP-ZDUSSCGKSA-N [(3S)-3-methylpiperazin-1-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound C[C@H]1CN(CCN1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F BMQCLTSPZXCHIP-ZDUSSCGKSA-N 0.000 claims 1
FKRJOLGOCURNRA-ZDUSSCGKSA-N [(3S)-3-methylpiperazin-1-yl]-[6-[6-(trifluoromethyl)pyridin-3-yl]oxyquinolin-2-yl]methanone Chemical compound C[C@H]1CN(CCN1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC=1C=NC(=CC1)C(F)(F)F FKRJOLGOCURNRA-ZDUSSCGKSA-N 0.000 claims 1
XVBZCTDRLDACGG-HXUWFJFHSA-N [(3S)-3-propan-2-ylpiperazin-1-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound C(C)(C)[C@H]1CN(CCN1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F XVBZCTDRLDACGG-HXUWFJFHSA-N 0.000 claims 1
DOILHXAUWXGMJF-CALCHBBNSA-N [(3S,4R)-3,4-dihydroxypyrrolidin-1-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound O[C@@H]1CN(C[C@@H]1O)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F DOILHXAUWXGMJF-CALCHBBNSA-N 0.000 claims 1
VYYZMFZEQATNPL-CALCHBBNSA-N [(3S,4R)-3,4-dihydroxypyrrolidin-1-yl]-[6-[6-(trifluoromethyl)pyridin-3-yl]oxyquinolin-2-yl]methanone Chemical compound O[C@@H]1CN(C[C@@H]1O)C(=O)C1=NC2=CC=C(C=C2C=C1)OC=1C=NC(=CC1)C(F)(F)F VYYZMFZEQATNPL-CALCHBBNSA-N 0.000 claims 1
XFRFXZAJYNPMTM-KDURUIRLSA-N [(3S,4R)-3,4-dimethoxypyrrolidin-1-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound CO[C@@H]1CN(C[C@@H]1OC)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F XFRFXZAJYNPMTM-KDURUIRLSA-N 0.000 claims 1
VOCREZZJJXIVFU-KZULUSFZSA-N [(3S,4R)-3-hydroxy-4-methylpyrrolidin-1-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound O[C@@H]1CN(C[C@H]1C)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F VOCREZZJJXIVFU-KZULUSFZSA-N 0.000 claims 1
TXJXSZAKCSJIGX-ROUUACIJSA-N [(3S,4S)-3-hydroxy-4-methylsulfanylpyrrolidin-1-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound O[C@H]1CN(C[C@@H]1SC)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F TXJXSZAKCSJIGX-ROUUACIJSA-N 0.000 claims 1
OQKKLRHGIGTVPK-GASCZTMLSA-N [(3S,5R)-3,5-bis(hydroxymethyl)piperidin-1-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound OC[C@@H]1CN(C[C@@H](C1)CO)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F OQKKLRHGIGTVPK-GASCZTMLSA-N 0.000 claims 1
JASOGYNCKLULCT-JLSDUUJJSA-N [(3aR,4S,6aS)-4-amino-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-2-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound N[C@H]1CC[C@@H]2CN(C[C@@H]21)C(=O)C2=NC1=CC=C(C=C1C=C2)OC2=NC=C(C=C2)C(F)(F)F JASOGYNCKLULCT-JLSDUUJJSA-N 0.000 claims 1
LRHWMSBOYROARN-GASCZTMLSA-N [(3aS,6aR)-2,3,3a,4,6,6a-hexahydro-1H-pyrrolo[3,4-c]pyrrol-5-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound C1N(C[C@@H]2[C@H]1CNC2)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F LRHWMSBOYROARN-GASCZTMLSA-N 0.000 claims 1
KXGFIYRECTWTET-IFXJQAMLSA-N [(3aS,6aS)-2,3,3a,4,6,6a-hexahydro-1H-pyrrolo[2,3-c]pyrrol-5-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound N1[C@H]2[C@@H](CC1)CN(C2)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F KXGFIYRECTWTET-IFXJQAMLSA-N 0.000 claims 1
LKWCXSGGHCIGOO-SBUREZEXSA-N [(5S,8S)-8-hydroxy-1-azaspiro[4.4]nonan-1-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound O[C@@H]1C[C@]2(CCCN2C(=O)C2=NC3=CC=C(C=C3C=C2)OC2=NC=C(C=C2)C(F)(F)F)CC1 LKWCXSGGHCIGOO-SBUREZEXSA-N 0.000 claims 1
WVGGOYFEVTXPEO-DLBZAZTESA-N [(7S,8aR)-7-fluoro-3,4,6,7,8,8a-hexahydro-1H-pyrrolo[1,2-a]pyrazin-2-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound F[C@H]1C[C@H]2N(CCN(C2)C(=O)C2=NC3=CC=C(C=C3C=C2)OC2=NC=C(C=C2)C(F)(F)F)C1 WVGGOYFEVTXPEO-DLBZAZTESA-N 0.000 claims 1
WVGGOYFEVTXPEO-IRXDYDNUSA-N [(7S,8aS)-7-fluoro-3,4,6,7,8,8a-hexahydro-1H-pyrrolo[1,2-a]pyrazin-2-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound F[C@H]1C[C@@H]2N(CCN(C2)C(=O)C2=NC3=CC=C(C=C3C=C2)OC2=NC=C(C=C2)C(F)(F)F)C1 WVGGOYFEVTXPEO-IRXDYDNUSA-N 0.000 claims 1
QSZWAWUMBWETMU-INIZCTEOSA-N [(8aS)-7,7-difluoro-1,3,4,6,8,8a-hexahydropyrrolo[1,2-a]pyrazin-2-yl]-[6-[5-(difluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound FC1(C[C@@H]2N(CCN(C2)C(=O)C2=NC3=CC=C(C=C3C=C2)OC2=NC=C(C=C2)C(F)F)C1)F QSZWAWUMBWETMU-INIZCTEOSA-N 0.000 claims 1
BRVAMCZNBIFERA-INIZCTEOSA-N [(8aS)-7,7-difluoro-1,3,4,6,8,8a-hexahydropyrrolo[1,2-a]pyrazin-2-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound FC1(C[C@@H]2N(CCN(C2)C(=O)C2=NC3=CC=C(C=C3C=C2)OC2=NC=C(C=C2)C(F)(F)F)C1)F BRVAMCZNBIFERA-INIZCTEOSA-N 0.000 claims 1
BJCGJVZHVQWYCP-UHFFFAOYSA-N [2-(difluoromethyl)piperazin-1-yl]-[6-[5-(difluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound FC(C1N(CCNC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)F)F BJCGJVZHVQWYCP-UHFFFAOYSA-N 0.000 claims 1
NTJUSWRVFLTWST-UHFFFAOYSA-N [2-(difluoromethyl)piperazin-1-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound FC(C1N(CCNC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F)F NTJUSWRVFLTWST-UHFFFAOYSA-N 0.000 claims 1
XRPLISBDPHMICK-UHFFFAOYSA-N [2-(fluoromethyl)morpholin-4-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound FCC1CN(CCO1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F XRPLISBDPHMICK-UHFFFAOYSA-N 0.000 claims 1
DPANWAQZCHDYNI-UHFFFAOYSA-N [2-(hydroxymethyl)morpholin-4-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound OCC1CN(CCO1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F DPANWAQZCHDYNI-UHFFFAOYSA-N 0.000 claims 1
OHQRBQSZTFJYPN-UHFFFAOYSA-N [2-(trifluoromethyl)piperazin-1-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound FC(C1N(CCNC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F)(F)F OHQRBQSZTFJYPN-UHFFFAOYSA-N 0.000 claims 1
JNGDMLXDVDNWCJ-UHFFFAOYSA-N [2-[(dimethylamino)methyl]morpholin-4-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound CN(C)CC1CN(CCO1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F JNGDMLXDVDNWCJ-UHFFFAOYSA-N 0.000 claims 1
SRBXCTLXOWKJNZ-UHFFFAOYSA-N [2-[4-(trifluoromethyl)phenyl]pyrrolidin-1-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound FC(C1=CC=C(C=C1)C1N(CCC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F)(F)F SRBXCTLXOWKJNZ-UHFFFAOYSA-N 0.000 claims 1
OYHLHRIWKNFGIG-UHFFFAOYSA-N [3-(1,2,4-triazol-1-yl)azetidin-1-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound N1(N=CN=C1)C1CN(C1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F OYHLHRIWKNFGIG-UHFFFAOYSA-N 0.000 claims 1
SUALZRSRONPDNT-UHFFFAOYSA-N [3-(2,2,2-trifluoroethylamino)azetidin-1-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound FC(CNC1CN(C1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F)(F)F SUALZRSRONPDNT-UHFFFAOYSA-N 0.000 claims 1
MQESYUJPMRIRJH-UHFFFAOYSA-N [3-(2,2-difluoroethoxy)azetidin-1-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound FC(COC1CN(C1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F)F MQESYUJPMRIRJH-UHFFFAOYSA-N 0.000 claims 1
DUCRZHUKWIBVEP-UHFFFAOYSA-N [3-(2-methoxyethoxy)azetidin-1-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound COCCOC1CN(C1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F DUCRZHUKWIBVEP-UHFFFAOYSA-N 0.000 claims 1
IIGHWIYRODPGEC-UHFFFAOYSA-N [3-(3-methyl-1,2,4-oxadiazol-5-yl)piperidin-1-yl]-(6-pyridin-2-yloxyquinolin-2-yl)methanone Chemical compound CC1=NOC(=N1)C1CN(CCC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=CC=C1 IIGHWIYRODPGEC-UHFFFAOYSA-N 0.000 claims 1
ATBZVMOOFLIUIT-UHFFFAOYSA-N [3-(4-bromophenoxy)azetidin-1-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound BrC1=CC=C(OC2CN(C2)C(=O)C2=NC3=CC=C(C=C3C=C2)OC2=NC=C(C=C2)C(F)(F)F)C=C1 ATBZVMOOFLIUIT-UHFFFAOYSA-N 0.000 claims 1
NNTPBIUZZQSEKP-UHFFFAOYSA-N [3-(4-chlorophenoxy)azetidin-1-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound ClC1=CC=C(OC2CN(C2)C(=O)C2=NC3=CC=C(C=C3C=C2)OC2=NC=C(C=C2)C(F)(F)F)C=C1 NNTPBIUZZQSEKP-UHFFFAOYSA-N 0.000 claims 1
DYCBLARGWSKQBV-UHFFFAOYSA-N [3-(azetidin-1-yl)pyrrolidin-1-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound N1(CCC1)C1CN(CC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F DYCBLARGWSKQBV-UHFFFAOYSA-N 0.000 claims 1
DSWRDHDROLBZDO-UHFFFAOYSA-N [3-(difluoromethyl)piperazin-1-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound FC(C1CN(CCN1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F)F DSWRDHDROLBZDO-UHFFFAOYSA-N 0.000 claims 1
PSRJPWCAHYKDDX-UHFFFAOYSA-N [3-(ethoxymethyl)-3-fluoropyrrolidin-1-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound C(C)OCC1(CN(CC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F)F PSRJPWCAHYKDDX-UHFFFAOYSA-N 0.000 claims 1
MCYNAILAOQRICR-UHFFFAOYSA-N [3-(hydroxymethyl)-3-methylazetidin-1-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound OCC1(CN(C1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F)C MCYNAILAOQRICR-UHFFFAOYSA-N 0.000 claims 1
OSPYCYCCLNKMPL-UHFFFAOYSA-N [3-(hydroxymethyl)pyrrolidin-1-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound OCC1CN(CC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F OSPYCYCCLNKMPL-UHFFFAOYSA-N 0.000 claims 1
PMADMDHWOUCDAR-UHFFFAOYSA-N [3-(methoxymethyl)-3-methylazetidin-1-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound COCC1(CN(C1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F)C PMADMDHWOUCDAR-UHFFFAOYSA-N 0.000 claims 1
WBLQTPNYWQVGCT-UHFFFAOYSA-N [3-(methoxymethyl)azetidin-1-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound COCC1CN(C1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F WBLQTPNYWQVGCT-UHFFFAOYSA-N 0.000 claims 1
WRECESGKKOPFJT-UHFFFAOYSA-N [3-(trifluoromethyl)piperazin-1-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound FC(C1CN(CCN1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F)(F)F WRECESGKKOPFJT-UHFFFAOYSA-N 0.000 claims 1
GTOFFVNUDBXLGX-MRXNPFEDSA-N [3-[(3R)-3-fluoropyrrolidin-1-yl]azetidin-1-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound F[C@H]1CN(CC1)C1CN(C1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F GTOFFVNUDBXLGX-MRXNPFEDSA-N 0.000 claims 1
GTOFFVNUDBXLGX-INIZCTEOSA-N [3-[(3S)-3-fluoropyrrolidin-1-yl]azetidin-1-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound F[C@@H]1CN(CC1)C1CN(C1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F GTOFFVNUDBXLGX-INIZCTEOSA-N 0.000 claims 1
PLDVGXFOXHGNIU-UHFFFAOYSA-N [3-fluoro-3-(2-methoxyethoxymethyl)pyrrolidin-1-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound FC1(CN(CC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F)COCCOC PLDVGXFOXHGNIU-UHFFFAOYSA-N 0.000 claims 1
IHMRERKJAQMTFQ-UHFFFAOYSA-N [3-fluoro-3-(methoxymethyl)pyrrolidin-1-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound FC1(CN(CC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F)COC IHMRERKJAQMTFQ-UHFFFAOYSA-N 0.000 claims 1
BOGQCJMOWJYRTP-UHFFFAOYSA-N [3-fluoro-3-(phenoxymethyl)pyrrolidin-1-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound FC1(CN(CC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F)COC1=CC=CC=C1 BOGQCJMOWJYRTP-UHFFFAOYSA-N 0.000 claims 1
SDUIVXNMVJDMFB-UHFFFAOYSA-N [3-fluoro-3-(pyridin-3-yloxymethyl)pyrrolidin-1-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound FC1(CN(CC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F)COC=1C=NC=CC1 SDUIVXNMVJDMFB-UHFFFAOYSA-N 0.000 claims 1
SCBMNGITEASPSA-UHFFFAOYSA-N [3-fluoro-3-(pyridin-4-yloxymethyl)pyrrolidin-1-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound FC1(CN(CC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F)COC1=CC=NC=C1 SCBMNGITEASPSA-UHFFFAOYSA-N 0.000 claims 1
QYPGRKGSCYPOAK-UHFFFAOYSA-N [4-(1,3-oxazol-2-ylmethyl)piperazin-1-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound O1C(=NC=C1)CN1CCN(CC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F QYPGRKGSCYPOAK-UHFFFAOYSA-N 0.000 claims 1
MKRBOYZINNNZHF-UHFFFAOYSA-N [4-(1,3-oxazol-4-ylmethyl)piperazin-1-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound O1C=NC(=C1)CN1CCN(CC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F MKRBOYZINNNZHF-UHFFFAOYSA-N 0.000 claims 1
ZXGATIMANGRSHS-UHFFFAOYSA-N [4-(1,5-dimethylpyrazol-4-yl)sulfonylpiperazin-1-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound CN1N=CC(=C1C)S(=O)(=O)N1CCN(CC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F ZXGATIMANGRSHS-UHFFFAOYSA-N 0.000 claims 1
LUTRLUAHMPWVJS-UHFFFAOYSA-N [4-(1-methylpyrazol-4-yl)sulfonylpiperazin-1-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound CN1N=CC(=C1)S(=O)(=O)N1CCN(CC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F LUTRLUAHMPWVJS-UHFFFAOYSA-N 0.000 claims 1
KJVYQCIXUQIREB-UHFFFAOYSA-N [4-(2,2,2-trifluoroethyl)piperazin-1-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound FC(CN1CCN(CC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F)(F)F KJVYQCIXUQIREB-UHFFFAOYSA-N 0.000 claims 1
QZMOJBPVJPWVBQ-UHFFFAOYSA-N [4-(2,2-difluoroethyl)piperazin-1-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound FC(CN1CCN(CC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F)F QZMOJBPVJPWVBQ-UHFFFAOYSA-N 0.000 claims 1
RUOFTXAXZVRPMY-UHFFFAOYSA-N [4-(2-hydroxyethyl)piperazin-1-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound OCCN1CCN(CC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F RUOFTXAXZVRPMY-UHFFFAOYSA-N 0.000 claims 1
DNJUBUSKKRFBCH-UHFFFAOYSA-N [4-(3,3-difluoroazetidin-1-yl)piperidin-1-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound FC1(CN(C1)C1CCN(CC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F)F DNJUBUSKKRFBCH-UHFFFAOYSA-N 0.000 claims 1
MDLJCOUVJTUPAV-UHFFFAOYSA-N [4-(5-chloropyridin-2-yl)piperazin-1-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound ClC=1C=CC(=NC1)N1CCN(CC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F MDLJCOUVJTUPAV-UHFFFAOYSA-N 0.000 claims 1
XANIPAUMKLWRIB-UHFFFAOYSA-N [4-(benzenesulfonyl)piperazin-1-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound C1(=CC=CC=C1)S(=O)(=O)N1CCN(CC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F XANIPAUMKLWRIB-UHFFFAOYSA-N 0.000 claims 1
NMWCVOSZCSSBSK-UHFFFAOYSA-N [4-(hydroxymethyl)piperidin-1-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound OCC1CCN(CC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F NMWCVOSZCSSBSK-UHFFFAOYSA-N 0.000 claims 1
AZRQWGKENMINSA-UHFFFAOYSA-N [4-(morpholine-4-carbonyl)piperazin-1-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound N1(CCOCC1)C(=O)N1CCN(CC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F AZRQWGKENMINSA-UHFFFAOYSA-N 0.000 claims 1
WBVYOVKBLKFROQ-UHFFFAOYSA-N [4-(oxan-4-ylsulfonyl)piperazin-1-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound O1CCC(CC1)S(=O)(=O)N1CCN(CC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F WBVYOVKBLKFROQ-UHFFFAOYSA-N 0.000 claims 1
MJKKENWSLIMHIA-UHFFFAOYSA-N [4-(oxetan-3-yl)piperazin-1-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound O1CC(C1)N1CCN(CC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F MJKKENWSLIMHIA-UHFFFAOYSA-N 0.000 claims 1
HFTKWBPVBBFCGL-UHFFFAOYSA-N [4-(oxolan-3-ylmethylsulfonyl)piperazin-1-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound O1CC(CC1)CS(=O)(=O)N1CCN(CC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F HFTKWBPVBBFCGL-UHFFFAOYSA-N 0.000 claims 1
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QJSJCBVAASSSIA-UHFFFAOYSA-N [4-(pyridin-2-ylmethyl)piperazin-1-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound N1=C(C=CC=C1)CN1CCN(CC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F QJSJCBVAASSSIA-UHFFFAOYSA-N 0.000 claims 1
FKTKHLBUCVPSGU-TZIWHRDSSA-N [4-[(1R,4R)-2-oxa-5-azabicyclo[2.2.1]heptan-5-yl]piperidin-1-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound [C@H]12OC[C@H](N(C1)C1CCN(CC1)C(=O)C1=NC3=CC=C(C=C3C=C1)OC1=NC=C(C=C1)C(F)(F)F)C2 FKTKHLBUCVPSGU-TZIWHRDSSA-N 0.000 claims 1
FKTKHLBUCVPSGU-FPOVZHCZSA-N [4-[(1S,4S)-2-oxa-5-azabicyclo[2.2.1]heptan-5-yl]piperidin-1-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound [C@@H]12OC[C@@H](N(C1)C1CCN(CC1)C(=O)C1=NC3=CC=C(C=C3C=C1)OC1=NC=C(C=C1)C(F)(F)F)C2 FKTKHLBUCVPSGU-FPOVZHCZSA-N 0.000 claims 1
CZBLFJZCMPZXHH-UHFFFAOYSA-N [4-[(3-methyloxetan-3-yl)methyl]piperazin-1-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound CC1(COC1)CN1CCN(CC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F CZBLFJZCMPZXHH-UHFFFAOYSA-N 0.000 claims 1
KRVWLZGWGKNFOD-UHFFFAOYSA-N [4-[1-(2-methoxyethyl)pyrazol-4-yl]sulfonylpiperazin-1-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound COCCN1N=CC(=C1)S(=O)(=O)N1CCN(CC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F KRVWLZGWGKNFOD-UHFFFAOYSA-N 0.000 claims 1
YPHUVGISAADAOG-UHFFFAOYSA-N [4-fluoro-4-(methoxymethyl)piperidin-1-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound FC1(CCN(CC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F)COC YPHUVGISAADAOG-UHFFFAOYSA-N 0.000 claims 1
YLSQDEVSDJGKTB-UHFFFAOYSA-N [6-(4-methylsulfonylphenoxy)quinolin-2-yl]-piperazin-1-ylmethanone Chemical compound CS(=O)(=O)C1=CC=C(OC=2C=C3C=CC(=NC3=CC2)C(=O)N2CCNCC2)C=C1 YLSQDEVSDJGKTB-UHFFFAOYSA-N 0.000 claims 1
AATJHIFTVCAMGM-UHFFFAOYSA-N [6-(5-fluoropyridin-2-yl)oxyquinolin-2-yl]-piperazin-1-ylmethanone Chemical compound FC=1C=CC(=NC1)OC=1C=C2C=CC(=NC2=CC1)C(=O)N1CCNCC1 AATJHIFTVCAMGM-UHFFFAOYSA-N 0.000 claims 1
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PZWCVLUOYWRCAT-CYBMUJFWSA-N [6-[5-(difluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]-[(3R)-3-methylpiperazin-1-yl]methanone Chemical compound FC(C=1C=CC(=NC1)OC=1C=C2C=CC(=NC2=CC1)C(=O)N1C[C@H](NCC1)C)F PZWCVLUOYWRCAT-CYBMUJFWSA-N 0.000 claims 1
AKBXGQFGLLOSAG-HNNXBMFYSA-N [6-[5-(difluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]-[(3S)-3-(hydroxymethyl)piperazin-1-yl]methanone Chemical compound FC(C=1C=CC(=NC1)OC=1C=C2C=CC(=NC2=CC1)C(=O)N1C[C@H](NCC1)CO)F AKBXGQFGLLOSAG-HNNXBMFYSA-N 0.000 claims 1
FBRAUGXMWZJVLC-INIZCTEOSA-N [6-[5-(difluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]-[(3S)-3-(methoxymethyl)piperazin-1-yl]methanone Chemical compound FC(C=1C=CC(=NC1)OC=1C=C2C=CC(=NC2=CC1)C(=O)N1C[C@H](NCC1)COC)F FBRAUGXMWZJVLC-INIZCTEOSA-N 0.000 claims 1
ILSFMSYXOKNJSO-AWEZNQCLSA-N [6-[5-(difluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]-[(3S)-3-fluoropyrrolidin-1-yl]methanone Chemical compound FC(C=1C=CC(=NC1)OC=1C=C2C=CC(=NC2=CC1)C(=O)N1C[C@H](CC1)F)F ILSFMSYXOKNJSO-AWEZNQCLSA-N 0.000 claims 1
PZWCVLUOYWRCAT-ZDUSSCGKSA-N [6-[5-(difluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]-[(3S)-3-methylpiperazin-1-yl]methanone Chemical compound FC(C=1C=CC(=NC1)OC=1C=C2C=CC(=NC2=CC1)C(=O)N1C[C@@H](NCC1)C)F PZWCVLUOYWRCAT-ZDUSSCGKSA-N 0.000 claims 1
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IGURXAMRRWYRLR-CYBMUJFWSA-N [6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]-[(2R)-2,3,3-trimethylazetidin-1-yl]methanone Chemical compound FC(C=1C=CC(=NC1)OC=1C=C2C=CC(=NC2=CC1)C(=O)N1[C@@H](C(C1)(C)C)C)(F)F IGURXAMRRWYRLR-CYBMUJFWSA-N 0.000 claims 1
IGURXAMRRWYRLR-ZDUSSCGKSA-N [6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]-[(2S)-2,3,3-trimethylazetidin-1-yl]methanone Chemical compound FC(C=1C=CC(=NC1)OC=1C=C2C=CC(=NC2=CC1)C(=O)N1[C@H](C(C1)(C)C)C)(F)F IGURXAMRRWYRLR-ZDUSSCGKSA-N 0.000 claims 1
ZTTBOGSQOXWSMZ-UHFFFAOYSA-N [6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]-[3-(trifluoromethyl)pyrrolidin-1-yl]methanone Chemical compound FC(C=1C=CC(=NC1)OC=1C=C2C=CC(=NC2=CC1)C(=O)N1CC(CC1)C(F)(F)F)(F)F ZTTBOGSQOXWSMZ-UHFFFAOYSA-N 0.000 claims 1
JVTKQBUKBCJINP-UHFFFAOYSA-N [6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]-[4-(3,3,3-trifluoropropyl)piperazin-1-yl]methanone Chemical compound FC(C=1C=CC(=NC1)OC=1C=C2C=CC(=NC2=CC1)C(=O)N1CCN(CC1)CCC(F)(F)F)(F)F JVTKQBUKBCJINP-UHFFFAOYSA-N 0.000 claims 1
YRKPUISPHFXDPJ-UHFFFAOYSA-N [6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]-[4-(3,3,3-trifluoropropylsulfonyl)piperazin-1-yl]methanone Chemical compound FC(C=1C=CC(=NC1)OC=1C=C2C=CC(=NC2=CC1)C(=O)N1CCN(CC1)S(=O)(=O)CCC(F)(F)F)(F)F YRKPUISPHFXDPJ-UHFFFAOYSA-N 0.000 claims 1
125000003545 alkoxy group Chemical group 0.000 claims 1
YDGBVINIBCLRIA-UHFFFAOYSA-N azepan-1-yl-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound N1(CCCCCC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F YDGBVINIBCLRIA-UHFFFAOYSA-N 0.000 claims 1
125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 claims 1
VLOYGTFAWSHKJJ-UHFFFAOYSA-N azetidin-1-yl-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound N1(CCC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F VLOYGTFAWSHKJJ-UHFFFAOYSA-N 0.000 claims 1
125000004567 azetidin-3-yl group Chemical group N1CC(C1)* 0.000 claims 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
238000006243 chemical reaction Methods 0.000 claims 1
238000002512 chemotherapy Methods 0.000 claims 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
UXMTZYPJMHGAHV-UHFFFAOYSA-N cyclopropyl-[4-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinoline-2-carbonyl]piperazin-1-yl]methanone Chemical compound C1(CC1)C(=O)N1CCN(CC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F UXMTZYPJMHGAHV-UHFFFAOYSA-N 0.000 claims 1
201000003146 cystitis Diseases 0.000 claims 1
201000010099 disease Diseases 0.000 claims 1
125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims 1
230000006698 induction Effects 0.000 claims 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 1
SFMSJHSTEPWSCR-UHFFFAOYSA-N morpholin-4-yl-(6-pyridin-2-yloxyquinolin-2-yl)methanone Chemical compound N1(CCOCC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=CC=C1 SFMSJHSTEPWSCR-UHFFFAOYSA-N 0.000 claims 1
PBAAHWVLRFYYSS-UHFFFAOYSA-N morpholin-4-yl-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound N1(CCOCC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F PBAAHWVLRFYYSS-UHFFFAOYSA-N 0.000 claims 1
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125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims 1
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OOBIXNNGCDYKPF-UHFFFAOYSA-N piperazin-1-yl-(6-pyrimidin-2-yloxyquinolin-2-yl)methanone Chemical compound N1(CCNCC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=CC=N1 OOBIXNNGCDYKPF-UHFFFAOYSA-N 0.000 claims 1
OKFZWUFFIAFNGA-UHFFFAOYSA-N piperazin-1-yl-[6-[4-(trifluoromethyl)phenoxy]quinolin-2-yl]methanone Chemical compound N1(CCNCC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=CC=C(C=C1)C(F)(F)F OKFZWUFFIAFNGA-UHFFFAOYSA-N 0.000 claims 1
NGASFLWLHULJGT-UHFFFAOYSA-N piperazin-1-yl-[6-[4-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound N1(CCNCC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=CC(=C1)C(F)(F)F NGASFLWLHULJGT-UHFFFAOYSA-N 0.000 claims 1
REGLDXIVBNZLDY-UHFFFAOYSA-N piperazin-1-yl-[6-[4-(trifluoromethylsulfonyl)phenoxy]quinolin-2-yl]methanone Chemical compound N1(CCNCC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=CC=C(C=C1)S(=O)(=O)C(F)(F)F REGLDXIVBNZLDY-UHFFFAOYSA-N 0.000 claims 1
QJXZNXQOXMODEI-UHFFFAOYSA-N piperazin-1-yl-[6-[5-(trifluoromethoxy)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound N1(CCNCC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)OC(F)(F)F QJXZNXQOXMODEI-UHFFFAOYSA-N 0.000 claims 1
GUXGKEDVVNKUKU-UHFFFAOYSA-N piperazin-1-yl-[6-[5-(trifluoromethyl)pyrazin-2-yl]oxyquinolin-2-yl]methanone Chemical compound N1(CCNCC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(N=C1)C(F)(F)F GUXGKEDVVNKUKU-UHFFFAOYSA-N 0.000 claims 1
PSKAASYIVOPYMH-UHFFFAOYSA-N piperazin-1-yl-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound N1(CCNCC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F PSKAASYIVOPYMH-UHFFFAOYSA-N 0.000 claims 1
LXKNJBPJHWTTRY-UHFFFAOYSA-N piperazin-1-yl-[6-[5-(trifluoromethyl)pyrimidin-2-yl]oxyquinolin-2-yl]methanone Chemical compound N1(CCNCC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=N1)C(F)(F)F LXKNJBPJHWTTRY-UHFFFAOYSA-N 0.000 claims 1
IVDZDNBTEATXQK-UHFFFAOYSA-N piperazin-1-yl-[6-[6-(trifluoromethyl)pyridazin-3-yl]oxyquinolin-2-yl]methanone Chemical compound N1(CCNCC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC=1N=NC(=CC1)C(F)(F)F IVDZDNBTEATXQK-UHFFFAOYSA-N 0.000 claims 1
AJUUAPCYEULXLY-UHFFFAOYSA-N piperazin-1-yl-[6-[6-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound N1(CCNCC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC(=CC=C1)C(F)(F)F AJUUAPCYEULXLY-UHFFFAOYSA-N 0.000 claims 1
YHEYHLFSESANJU-UHFFFAOYSA-N piperazin-1-yl-[6-[6-(trifluoromethyl)pyridin-3-yl]oxyquinolin-2-yl]methanone Chemical compound N1(CCNCC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC=1C=NC(=CC1)C(F)(F)F YHEYHLFSESANJU-UHFFFAOYSA-N 0.000 claims 1
PKKQBABRTADZDG-UHFFFAOYSA-N piperazin-1-yl-[6-[[5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl]oxy]quinolin-2-yl]methanone Chemical compound N1(CCNCC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC=1SC(=NN1)C(F)(F)F PKKQBABRTADZDG-UHFFFAOYSA-N 0.000 claims 1
IVXQBCUBSIPQGU-UHFFFAOYSA-N piperazine-1-carboxamide Chemical compound NC(=O)N1CCNCC1 IVXQBCUBSIPQGU-UHFFFAOYSA-N 0.000 claims 1
GXQNYIDINGGTIY-UHFFFAOYSA-N piperidin-1-yl-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound N1(CCCCC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F GXQNYIDINGGTIY-UHFFFAOYSA-N 0.000 claims 1
125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims 1
125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 claims 1
125000006514 pyridin-2-ylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims 1
125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims 1
JLCKYXMWUDMBNX-UHFFFAOYSA-N pyrrolidin-1-yl-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound N1(CCCC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F JLCKYXMWUDMBNX-UHFFFAOYSA-N 0.000 claims 1
125000004550 quinolin-6-yl group Chemical group N1=CC=CC2=CC(=CC=C12)* 0.000 claims 1
150000003254 radicals Chemical class 0.000 claims 1
230000001105 regulatory effect Effects 0.000 claims 1
239000000126 substance Substances 0.000 claims 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
238000002560 therapeutic procedure Methods 0.000 claims 1
125000006300 thietan-3-yl group Chemical group [H]C1([H])SC([H])([H])C1([H])* 0.000 claims 1
125000004571 thiomorpholin-4-yl group Chemical group N1(CCSCC1)* 0.000 claims 1
VKYAWNHEASWPLQ-UHFFFAOYSA-N thiomorpholin-4-yl-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone Chemical compound N1(CCSCC1)C(=O)C1=NC2=CC=C(C=C2C=C1)OC1=NC=C(C=C1)C(F)(F)F VKYAWNHEASWPLQ-UHFFFAOYSA-N 0.000 claims 1
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 1

JP2016550611A 2014-02-06 2015-02-04 ６−ヘテロアリールオキシ−および６−アリールオキシ−キノリン−２−カルボキシアミドならびにその使用 Expired - Fee Related JP6532474B2 (ja)