OA13151A - Aminoheteroaryl compounds as protein kinase inhibitors. - Google Patents

Info

Publication number

OA13151A

OA13151A OA1200500243A OA1200500243A OA13151A OA 13151 A OA13151 A OA 13151A OA 1200500243 A OA1200500243 A OA 1200500243A OA 1200500243 A OA1200500243 A OA 1200500243A OA 13151 A OA13151 A OA 13151A

Authority

OA

OAPI

Prior art keywords

phenyl

amino

pyridin

ethoxy

dichloro

Prior art date

2003-02-26

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• 229940045988 antineoplastic drug protein kinase inhibitors Drugs 0.000 title abstract description 3
• 239000003909 protein kinase inhibitor Substances 0.000 title abstract description 3
• 125000005214 aminoheteroaryl group Chemical group 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 263
• 238000000034 method Methods 0.000 claims abstract description 134
• 239000000203 mixture Substances 0.000 claims abstract description 123
• 239000003112 inhibitor Substances 0.000 claims abstract description 16
• 125000003118 aryl group Chemical group 0.000 claims description 166
• 125000001072 heteroaryl group Chemical group 0.000 claims description 160
• 229910052739 hydrogen Inorganic materials 0.000 claims description 132
• 239000001257 hydrogen Substances 0.000 claims description 129
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 123
• 125000000217 alkyl group Chemical group 0.000 claims description 121
• -1 C2.12alkynyl Chemical group 0.000 claims description 118
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 86
• 206010028980 Neoplasm Diseases 0.000 claims description 81
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 76
• 229910020008 S(O) Inorganic materials 0.000 claims description 76
• 239000002253 acid Substances 0.000 claims description 71
• 229910052736 halogen Inorganic materials 0.000 claims description 69
• 125000003342 alkenyl group Chemical group 0.000 claims description 61
• 125000000304 alkynyl group Chemical group 0.000 claims description 50
• 229910052757 nitrogen Inorganic materials 0.000 claims description 50
• 201000011510 cancer Diseases 0.000 claims description 49
• 150000002367 halogens Chemical class 0.000 claims description 43
• 150000002431 hydrogen Chemical group 0.000 claims description 41
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 39
• 125000005843 halogen group Chemical group 0.000 claims description 37
• 239000005711 Benzoic acid Substances 0.000 claims description 33
• 229960004365 benzoic acid Drugs 0.000 claims description 33
• 150000003839 salts Chemical class 0.000 claims description 33
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 32
• QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 30
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 26
• KIWSYRHAAPLJFJ-DNZSEPECSA-N n-[(e,2z)-4-ethyl-2-hydroxyimino-5-nitrohex-3-enyl]pyridine-3-carboxamide Chemical compound [O-][N+](=O)C(C)C(/CC)=C/C(=N/O)/CNC(=O)C1=CC=CN=C1 KIWSYRHAAPLJFJ-DNZSEPECSA-N 0.000 claims description 25
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 24
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 23
• YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 21
• 150000004677 hydrates Chemical class 0.000 claims description 21
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 20
• KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 18
• 239000004202 carbamide Substances 0.000 claims description 18
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 17
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 16
• 125000004429 atom Chemical group 0.000 claims description 16
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 15
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 15
• 150000002148 esters Chemical class 0.000 claims description 14
• 125000000623 heterocyclic group Chemical group 0.000 claims description 14
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 13
• CFAFEJHONLMPQY-UHFFFAOYSA-N beta-Dimethylamino-aethan-alpha-sulfonsaeure Natural products CN(C)CCS(O)(=O)=O CFAFEJHONLMPQY-UHFFFAOYSA-N 0.000 claims description 13
• 150000001412 amines Chemical class 0.000 claims description 12
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 12
• 229910052760 oxygen Inorganic materials 0.000 claims description 12
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 12
• 229910052717 sulfur Inorganic materials 0.000 claims description 12
• 230000002159 abnormal effect Effects 0.000 claims description 11
• 125000005842 heteroatom Chemical group 0.000 claims description 11
• 125000003545 alkoxy group Chemical group 0.000 claims description 10
• 229910052799 carbon Inorganic materials 0.000 claims description 10
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• 208000026310 Breast neoplasm Diseases 0.000 claims description 9
• PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 9
• 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 claims description 8
• JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 8
• CXWGKAYMVASWDQ-UHFFFAOYSA-N 1,2-dithiane Chemical compound C1CCSSC1 CXWGKAYMVASWDQ-UHFFFAOYSA-N 0.000 claims description 8
• WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims description 8
• WUEPMEXUMQVEGN-UHFFFAOYSA-N 2,2,2-trifluoroacetic acid;2,2,2-trifluoro-n-[2-[2-[(2,2,2-trifluoroacetyl)amino]ethylamino]ethyl]acetamide Chemical compound OC(=O)C(F)(F)F.FC(F)(F)C(=O)NCCNCCNC(=O)C(F)(F)F WUEPMEXUMQVEGN-UHFFFAOYSA-N 0.000 claims description 8
• RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical compound C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 claims description 8
• 201000009030 Carcinoma Diseases 0.000 claims description 8
• WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 claims description 8
• ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 8
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 8
• 230000010261 cell growth Effects 0.000 claims description 8
• LOZWAPSEEHRYPG-UHFFFAOYSA-N dithiane Natural products C1CSCCS1 LOZWAPSEEHRYPG-UHFFFAOYSA-N 0.000 claims description 8
• 239000003102 growth factor Substances 0.000 claims description 8
• ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims description 8
• CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 8
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
• WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 8
• USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 claims description 8
• PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 8
• ZVJHJDDKYZXRJI-UHFFFAOYSA-N pyrroline Natural products C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 claims description 8
• 150000003852 triazoles Chemical class 0.000 claims description 8
• KTZFIQVZRIPKSY-UHFFFAOYSA-N 2-(cyclopropylmethylamino)ethanesulfonic acid Chemical compound OS(=O)(=O)CCNCC1CC1 KTZFIQVZRIPKSY-UHFFFAOYSA-N 0.000 claims description 7
• MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 claims description 7
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 7
• 206010039491 Sarcoma Diseases 0.000 claims description 7
• FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 7
• 239000002246 antineoplastic agent Substances 0.000 claims description 7
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
• DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 claims description 7
• BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 7
• BVOMRRWJQOJMPA-UHFFFAOYSA-N 1,2,3-trithiane Chemical compound C1CSSSC1 BVOMRRWJQOJMPA-UHFFFAOYSA-N 0.000 claims description 6
• OIXSOQOJISAETD-UHFFFAOYSA-N 2-(diethylamino)ethanesulfonic acid Chemical compound CCN(CC)CCS(O)(=O)=O OIXSOQOJISAETD-UHFFFAOYSA-N 0.000 claims description 6
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 6
• 206010009944 Colon cancer Diseases 0.000 claims description 6
• 206010033128 Ovarian cancer Diseases 0.000 claims description 6
• 206010061535 Ovarian neoplasm Diseases 0.000 claims description 6
• 206010060862 Prostate cancer Diseases 0.000 claims description 6
• 230000001684 chronic effect Effects 0.000 claims description 6
• 208000014829 head and neck neoplasm Diseases 0.000 claims description 6
• VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims description 6
• BTGNLYUOHYOJKM-UHFFFAOYSA-N 2-(4-hydroxypiperidin-1-yl)ethanesulfonic acid Chemical compound OC1CCN(CCS(O)(=O)=O)CC1 BTGNLYUOHYOJKM-UHFFFAOYSA-N 0.000 claims description 5
• XARBMSAAZHEXEK-UHFFFAOYSA-N 2-piperidin-1-ylethanesulfonic acid Chemical compound OS(=O)(=O)CCN1CCCCC1 XARBMSAAZHEXEK-UHFFFAOYSA-N 0.000 claims description 5
• YSFZEZFZXVPKDS-UHFFFAOYSA-N 2-pyrrolidin-1-ylethanesulfonic acid Chemical compound OS(=O)(=O)CCN1CCCC1 YSFZEZFZXVPKDS-UHFFFAOYSA-N 0.000 claims description 5
• 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 5
• 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims description 5
• MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 claims description 5
• 208000008443 pancreatic carcinoma Diseases 0.000 claims description 5
• 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 5
• 125000001424 substituent group Chemical group 0.000 claims description 5
• DEORKGOOAYZFNO-UHFFFAOYSA-N 1-amino-3-pyrrolidin-1-ylpropan-2-ol Chemical compound NCC(O)CN1CCCC1 DEORKGOOAYZFNO-UHFFFAOYSA-N 0.000 claims description 4
• RNCYRKBMBSJWMX-UHFFFAOYSA-N 2-(4-acetylpiperazin-1-yl)ethanesulfonic acid Chemical compound CC(=O)N1CCN(CCS(O)(=O)=O)CC1 RNCYRKBMBSJWMX-UHFFFAOYSA-N 0.000 claims description 4
• IVJULNTWOMZJSH-UHFFFAOYSA-N 2-(cyclopropylamino)ethanesulfonic acid Chemical compound OS(=O)(=O)CCNC1CC1 IVJULNTWOMZJSH-UHFFFAOYSA-N 0.000 claims description 4
• AGKQHBSJYYFGAO-ZCFIWIBFSA-N 2-[(3r)-3-hydroxypyrrolidin-1-yl]ethanesulfonic acid Chemical compound O[C@@H]1CCN(CCS(O)(=O)=O)C1 AGKQHBSJYYFGAO-ZCFIWIBFSA-N 0.000 claims description 4
• 125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 claims description 4
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 4
• 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 4
• 241000124008 Mammalia Species 0.000 claims description 4
• 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 4
• 210000003169 central nervous system Anatomy 0.000 claims description 4
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 4
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• RWIVICVCHVMHMU-UHFFFAOYSA-N n-aminoethylmorpholine Chemical compound NCCN1CCOCC1 RWIVICVCHVMHMU-UHFFFAOYSA-N 0.000 claims description 4
• 239000011570 nicotinamide Substances 0.000 claims description 4
• 229960003966 nicotinamide Drugs 0.000 claims description 4
• 208000002154 non-small cell lung carcinoma Diseases 0.000 claims description 4
• 201000002528 pancreatic cancer Diseases 0.000 claims description 4
• 230000004044 response Effects 0.000 claims description 4
• 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims description 4
• 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 3
• 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims description 3
• SXGZJKUKBWWHRA-UHFFFAOYSA-N 2-(N-morpholiniumyl)ethanesulfonate Chemical compound [O-]S(=O)(=O)CC[NH+]1CCOCC1 SXGZJKUKBWWHRA-UHFFFAOYSA-N 0.000 claims description 3
• XWZAVKANWUQEDZ-UHFFFAOYSA-N 2-[4-(2-hydroxyacetyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC(=O)N1CCN(CCS(O)(=O)=O)CC1 XWZAVKANWUQEDZ-UHFFFAOYSA-N 0.000 claims description 3
• SDXGGNKSWPLCEN-UHFFFAOYSA-N 3-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]-5-ethenylpyridin-2-amine Chemical compound ClC=1C=CC(F)=C(Cl)C=1C(C)OC1=CC(C=C)=CN=C1N SDXGGNKSWPLCEN-UHFFFAOYSA-N 0.000 claims description 3
• KNWWGBNAUNTSRV-UHFFFAOYSA-N 4-methylpiperazine-1-carboxylic acid Chemical compound CN1CCN(C(O)=O)CC1 KNWWGBNAUNTSRV-UHFFFAOYSA-N 0.000 claims description 3
• YJKSBHPLLPUPHG-UHFFFAOYSA-N 4-pyrrolidin-1-ylpiperidine-1-carboxylic acid Chemical compound C1CN(C(=O)O)CCC1N1CCCC1 YJKSBHPLLPUPHG-UHFFFAOYSA-N 0.000 claims description 3
• XFXKQRFLZQWZIL-UHFFFAOYSA-N 5-[6-amino-5-[(2-chloro-3,6-difluorophenyl)methoxy]pyridin-3-yl]thiophene-2-carboxylic acid Chemical compound NC1=NC=C(C=2SC(=CC=2)C(O)=O)C=C1OCC1=C(F)C=CC(F)=C1Cl XFXKQRFLZQWZIL-UHFFFAOYSA-N 0.000 claims description 3
• IIOVWJFCOBWBOK-UHFFFAOYSA-N 5-[6-amino-5-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]pyridin-3-yl]-1h-pyridin-2-one Chemical compound ClC=1C=CC(F)=C(Cl)C=1C(C)OC(C(=NC=1)N)=CC=1C=1C=CC(=O)NC=1 IIOVWJFCOBWBOK-UHFFFAOYSA-N 0.000 claims description 3
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• 102000004190 Enzymes Human genes 0.000 claims description 3
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• XQGNDISABQARPN-UHFFFAOYSA-N FC=1C=CC(F)=C(Cl)C=1C(C)OC(C(=NC=1)N)=NC=1C1=CC=C(N)C=C1 Chemical compound FC=1C=CC(F)=C(Cl)C=1C(C)OC(C(=NC=1)N)=NC=1C1=CC=C(N)C=C1 XQGNDISABQARPN-UHFFFAOYSA-N 0.000 claims description 3
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• YAPQRZRSJVDLGL-UHFFFAOYSA-N NC1=CC=CC(C=2C=C(OCC=3C(=C(F)C=CC=3F)Cl)C(N)=NC=2)=C1 Chemical compound NC1=CC=CC(C=2C=C(OCC=3C(=C(F)C=CC=3F)Cl)C(N)=NC=2)=C1 YAPQRZRSJVDLGL-UHFFFAOYSA-N 0.000 claims description 3
• 208000000821 Parathyroid Neoplasms Diseases 0.000 claims description 3
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• MKSTXMDSWOHKOR-SCSAIBSYSA-N (3r)-3-aminopyrrolidine-1-carboxylic acid Chemical compound N[C@@H]1CCN(C(O)=O)C1 MKSTXMDSWOHKOR-SCSAIBSYSA-N 0.000 claims description 2
• NDYMQOUYJJXCKJ-UHFFFAOYSA-N (4-fluorophenyl)-morpholin-4-ylmethanone Chemical compound C1=CC(F)=CC=C1C(=O)N1CCOCC1 NDYMQOUYJJXCKJ-UHFFFAOYSA-N 0.000 claims description 2
• DYAUUAHGQMEAOO-UHFFFAOYSA-N 1-[3-[6-amino-5-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]pyridin-3-yl]prop-2-ynyl]-3-(3-pyrrolidin-1-ylpropyl)urea Chemical compound ClC=1C=CC(F)=C(Cl)C=1C(C)OC(C(=NC=1)N)=CC=1C#CCNC(=O)NCCCN1CCCC1 DYAUUAHGQMEAOO-UHFFFAOYSA-N 0.000 claims description 2
• UMQQWNRAHOAVIM-UHFFFAOYSA-N 1-[4-[4-[6-amino-5-[(2,4-dichlorophenyl)methoxy]pyridin-3-yl]benzoyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1C(=O)C1=CC=C(C=2C=C(OCC=3C(=CC(Cl)=CC=3)Cl)C(N)=NC=2)C=C1 UMQQWNRAHOAVIM-UHFFFAOYSA-N 0.000 claims description 2
• ZWXAPRUGWBKJSY-UHFFFAOYSA-N 1-[4-[4-[6-amino-5-[(2-chlorophenyl)methoxy]pyridin-3-yl]benzoyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1C(=O)C1=CC=C(C=2C=C(OCC=3C(=CC=CC=3)Cl)C(N)=NC=2)C=C1 ZWXAPRUGWBKJSY-UHFFFAOYSA-N 0.000 claims description 2
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• BQKSTOOQRYVIRH-UHFFFAOYSA-N [4-[5-amino-6-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]pyrazin-2-yl]phenyl]-[4-(cyclopropylamino)piperidin-1-yl]methanone Chemical compound ClC=1C=CC(F)=C(Cl)C=1C(C)OC(C(=NC=1)N)=NC=1C(C=C1)=CC=C1C(=O)N(CC1)CCC1NC1CC1 BQKSTOOQRYVIRH-UHFFFAOYSA-N 0.000 claims description 2
• AWXCPGBSMTVIDD-OZBJMMHXSA-N [4-[5-amino-6-[1-(2-chloro-3,6-difluorophenyl)ethoxy]pyrazin-2-yl]phenyl]-[(2s)-2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl]methanone Chemical compound C([C@@H]1CCCN1C(=O)C1=CC=C(C=C1)C=1N=C(C(=NC=1)N)OC(C)C=1C(=C(F)C=CC=1F)Cl)N1CCCC1 AWXCPGBSMTVIDD-OZBJMMHXSA-N 0.000 claims description 2
• QWSDYGXUBMHYCQ-UHFFFAOYSA-N [4-[6-amino-5-[(2,4,6-trifluorophenyl)methoxy]pyridin-3-yl]phenyl]-(4-pyrrolidin-1-ylpiperidin-1-yl)methanone Chemical compound NC1=NC=C(C=2C=CC(=CC=2)C(=O)N2CCC(CC2)N2CCCC2)C=C1OCC1=C(F)C=C(F)C=C1F QWSDYGXUBMHYCQ-UHFFFAOYSA-N 0.000 claims description 2
• PDVBXPVCRVLNPG-UHFFFAOYSA-N [4-[6-amino-5-[(2,6-dichlorophenyl)methoxy]pyridin-3-yl]phenyl]-(4-cyclopropylpiperazin-1-yl)methanone Chemical compound NC1=NC=C(C=2C=CC(=CC=2)C(=O)N2CCN(CC2)C2CC2)C=C1OCC1=C(Cl)C=CC=C1Cl PDVBXPVCRVLNPG-UHFFFAOYSA-N 0.000 claims description 2
• DBHGHGBVQVADRC-UHFFFAOYSA-N [4-[6-amino-5-[(2,6-dichlorophenyl)methoxy]pyridin-3-yl]phenyl]-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C1=CC=C(C=2C=C(OCC=3C(=CC=CC=3Cl)Cl)C(N)=NC=2)C=C1 DBHGHGBVQVADRC-UHFFFAOYSA-N 0.000 claims description 2
• KYWAICZFDNAJLJ-UHFFFAOYSA-N [4-[6-amino-5-[(2,6-dichlorophenyl)methoxy]pyridin-3-yl]phenyl]methanol Chemical compound NC1=NC=C(C=2C=CC(CO)=CC=2)C=C1OCC1=C(Cl)C=CC=C1Cl KYWAICZFDNAJLJ-UHFFFAOYSA-N 0.000 claims description 2
• FMSBDMWIAOEIRZ-SFHVURJKSA-N [4-[6-amino-5-[(2-chloro-3,6-difluorophenyl)methoxy]pyridin-3-yl]phenyl]-[(3s)-3-(dimethylamino)pyrrolidin-1-yl]methanone Chemical compound C1[C@@H](N(C)C)CCN1C(=O)C1=CC=C(C=2C=C(OCC=3C(=C(F)C=CC=3F)Cl)C(N)=NC=2)C=C1 FMSBDMWIAOEIRZ-SFHVURJKSA-N 0.000 claims description 2
• CKFJFVBNRJVPHK-INIZCTEOSA-N [4-[6-amino-5-[(2-chloro-3,6-difluorophenyl)methoxy]pyridin-3-yl]phenyl]-[(3s)-3-aminopyrrolidin-1-yl]methanone Chemical compound C1[C@@H](N)CCN1C(=O)C1=CC=C(C=2C=C(OCC=3C(=C(F)C=CC=3F)Cl)C(N)=NC=2)C=C1 CKFJFVBNRJVPHK-INIZCTEOSA-N 0.000 claims description 2
• NRHDODUAMRGLIM-UHFFFAOYSA-N [4-[6-amino-5-[(2-methylphenyl)methoxy]pyridin-3-yl]phenyl]-(3,5-dimethylpiperazin-1-yl)methanone Chemical compound C1C(C)NC(C)CN1C(=O)C1=CC=C(C=2C=C(OCC=3C(=CC=CC=3)C)C(N)=NC=2)C=C1 NRHDODUAMRGLIM-UHFFFAOYSA-N 0.000 claims description 2
• AWXKDRXUIGCEML-LRHAYUFXSA-N [4-[6-amino-5-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]pyridin-3-yl]phenyl]-[(3r)-3-hydroxypyrrolidin-1-yl]methanone Chemical compound ClC=1C=CC(F)=C(Cl)C=1C(C)OC(C(=NC=1)N)=CC=1C(C=C1)=CC=C1C(=O)N1CC[C@@H](O)C1 AWXKDRXUIGCEML-LRHAYUFXSA-N 0.000 claims description 2
• LVGDISGNKYDSAM-BVHINDKJSA-N [4-[6-amino-5-[1-(2,6-dichlorophenyl)ethoxy]pyridin-3-yl]phenyl]-[(2s)-2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl]methanone Chemical compound C([C@@H]1CCCN1C(=O)C1=CC=C(C=C1)C=1C=C(C(=NC=1)N)OC(C)C=1C(=CC=CC=1Cl)Cl)N1CCCC1 LVGDISGNKYDSAM-BVHINDKJSA-N 0.000 claims description 2
• MVQPAEHSIFYQTE-JWTNVVGKSA-N [4-[6-amino-5-[1-(3-fluoro-2-methoxyphenyl)ethoxy]pyridin-3-yl]phenyl]-[(3r,5s)-3,5-dimethylpiperazin-1-yl]methanone Chemical compound COC1=C(F)C=CC=C1C(C)OC1=CC(C=2C=CC(=CC=2)C(=O)N2C[C@@H](C)N[C@@H](C)C2)=CN=C1N MVQPAEHSIFYQTE-JWTNVVGKSA-N 0.000 claims description 2
• JTDKUTBYWTYQOI-TXEJJXNPSA-N [5-[5-amino-6-[(2-chloro-3,6-difluorophenyl)methoxy]pyrazin-2-yl]thiophen-2-yl]-[(3r,5s)-3,5-dimethylpiperazin-1-yl]methanone Chemical compound C1[C@@H](C)N[C@@H](C)CN1C(=O)C1=CC=C(C=2N=C(OCC=3C(=C(F)C=CC=3F)Cl)C(N)=NC=2)S1 JTDKUTBYWTYQOI-TXEJJXNPSA-N 0.000 claims description 2
• HYVNTCYPMPTACL-UHFFFAOYSA-N [5-[6-amino-5-[1-(2-chloro-3,6-difluorophenyl)ethoxy]pyridin-3-yl]pyridin-3-yl]-(4-methylpiperazin-1-yl)methanone Chemical compound FC=1C=CC(F)=C(Cl)C=1C(C)OC(C(=NC=1)N)=CC=1C(C=1)=CN=CC=1C(=O)N1CCN(C)CC1 HYVNTCYPMPTACL-UHFFFAOYSA-N 0.000 claims description 2
• DXJDJFDHQSGWOY-UHFFFAOYSA-N [6-[5-amino-6-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]pyrazin-2-yl]pyridin-3-yl]-(4-methylpiperazin-1-yl)methanone Chemical compound ClC=1C=CC(F)=C(Cl)C=1C(C)OC(C(=NC=1)N)=NC=1C(N=C1)=CC=C1C(=O)N1CCN(C)CC1 DXJDJFDHQSGWOY-UHFFFAOYSA-N 0.000 claims description 2
• 125000002723 alicyclic group Chemical group 0.000 claims description 2
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• ZGXGWQWGLVBNFC-UHFFFAOYSA-N 3-[(2,6-dichlorophenyl)methoxy]-5-(1h-indol-2-yl)pyridin-2-amine Chemical compound NC1=NC=C(C=2NC3=CC=CC=C3C=2)C=C1OCC1=C(Cl)C=CC=C1Cl ZGXGWQWGLVBNFC-UHFFFAOYSA-N 0.000 claims 1
• ZXMBERYHFCBLJE-UHFFFAOYSA-N 3-[(2,6-dichlorophenyl)methoxy]-5-(3-fluoro-4-phenylmethoxyphenyl)pyridin-2-amine Chemical compound NC1=NC=C(C=2C=C(F)C(OCC=3C=CC=CC=3)=CC=2)C=C1OCC1=C(Cl)C=CC=C1Cl ZXMBERYHFCBLJE-UHFFFAOYSA-N 0.000 claims 1
• ZYNPTNFUVBQQFS-UHFFFAOYSA-N 3-[(2,6-dichlorophenyl)methoxy]-5-(3-methoxyphenyl)pyridin-2-amine Chemical compound COC1=CC=CC(C=2C=C(OCC=3C(=CC=CC=3Cl)Cl)C(N)=NC=2)=C1 ZYNPTNFUVBQQFS-UHFFFAOYSA-N 0.000 claims 1
• FPPODYFUQVGTKV-UHFFFAOYSA-N 3-[(2,6-dichlorophenyl)methoxy]-5-(4-methoxyphenyl)pyridin-2-amine Chemical compound C1=CC(OC)=CC=C1C1=CN=C(N)C(OCC=2C(=CC=CC=2Cl)Cl)=C1 FPPODYFUQVGTKV-UHFFFAOYSA-N 0.000 claims 1
• NZJFYKXRMJBRCA-UHFFFAOYSA-N 3-[(2,6-dichlorophenyl)methoxy]-5-[2-(trifluoromethyl)phenyl]pyridin-2-amine Chemical compound NC1=NC=C(C=2C(=CC=CC=2)C(F)(F)F)C=C1OCC1=C(Cl)C=CC=C1Cl NZJFYKXRMJBRCA-UHFFFAOYSA-N 0.000 claims 1
• MFLQDFSYWLGYSY-UHFFFAOYSA-N 3-[(2,6-dichlorophenyl)methoxy]-5-[3-(2-morpholin-4-ylethoxy)phenyl]pyrazin-2-amine Chemical compound NC1=NC=C(C=2C=C(OCCN3CCOCC3)C=CC=2)N=C1OCC1=C(Cl)C=CC=C1Cl MFLQDFSYWLGYSY-UHFFFAOYSA-N 0.000 claims 1
• WCSMCFPDAJEIAG-UHFFFAOYSA-N 3-[(2,6-dichlorophenyl)methoxy]-5-[3-(morpholin-4-ylmethyl)-1h-indol-5-yl]pyridin-2-amine Chemical compound NC1=NC=C(C=2C=C3C(CN4CCOCC4)=CNC3=CC=2)C=C1OCC1=C(Cl)C=CC=C1Cl WCSMCFPDAJEIAG-UHFFFAOYSA-N 0.000 claims 1
• ZVHFPCWDJOSKIL-UHFFFAOYSA-N 3-[(2,6-dichlorophenyl)methoxy]-5-pyrimidin-5-ylpyridin-2-amine Chemical compound NC1=NC=C(C=2C=NC=NC=2)C=C1OCC1=C(Cl)C=CC=C1Cl ZVHFPCWDJOSKIL-UHFFFAOYSA-N 0.000 claims 1
• IXKDTCREAJHFDJ-UHFFFAOYSA-N 3-[(2,6-difluorophenyl)methoxy]-5-(1h-indol-4-yl)pyridin-2-amine Chemical compound NC1=NC=C(C=2C=3C=CNC=3C=CC=2)C=C1OCC1=C(F)C=CC=C1F IXKDTCREAJHFDJ-UHFFFAOYSA-N 0.000 claims 1
• YWGWVUMLUYNBJV-UHFFFAOYSA-N 3-[(2,6-difluorophenyl)methoxy]-5-[4-(2-morpholin-4-ylethoxy)phenyl]pyridin-2-amine Chemical compound NC1=NC=C(C=2C=CC(OCCN3CCOCC3)=CC=2)C=C1OCC1=C(F)C=CC=C1F YWGWVUMLUYNBJV-UHFFFAOYSA-N 0.000 claims 1
• BSSHQYHXECSEOH-UHFFFAOYSA-N 3-[(2-chloro-3,6-difluorophenyl)methoxy]-5-[2-[(dimethylamino)methyl]phenyl]pyridin-2-amine Chemical compound CN(C)CC1=CC=CC=C1C1=CN=C(N)C(OCC=2C(=C(F)C=CC=2F)Cl)=C1 BSSHQYHXECSEOH-UHFFFAOYSA-N 0.000 claims 1
• VYZOESQVOFQNBG-UHFFFAOYSA-N 3-[(2-chloro-3,6-difluorophenyl)methoxy]-5-[3-(morpholin-4-ylmethyl)-1h-indol-5-yl]pyridin-2-amine Chemical compound NC1=NC=C(C=2C=C3C(CN4CCOCC4)=CNC3=CC=2)C=C1OCC1=C(F)C=CC(F)=C1Cl VYZOESQVOFQNBG-UHFFFAOYSA-N 0.000 claims 1
• DIEYIAKMNKJYGI-UHFFFAOYSA-N 3-[(2-chloro-3,6-difluorophenyl)methoxy]-5-[3-(piperidin-1-ylmethyl)-1h-indol-5-yl]pyridin-2-amine Chemical compound NC1=NC=C(C=2C=C3C(CN4CCCCC4)=CNC3=CC=2)C=C1OCC1=C(F)C=CC(F)=C1Cl DIEYIAKMNKJYGI-UHFFFAOYSA-N 0.000 claims 1
• BSUBQGIFJMZOSF-UHFFFAOYSA-N 3-[(2-chloro-3,6-difluorophenyl)methoxy]-5-[3-(pyrrolidin-1-ylmethyl)-1h-indol-5-yl]pyrazin-2-amine Chemical compound NC1=NC=C(C=2C=C3C(CN4CCCC4)=CNC3=CC=2)N=C1OCC1=C(F)C=CC(F)=C1Cl BSUBQGIFJMZOSF-UHFFFAOYSA-N 0.000 claims 1
• VQQDCDDYVNCSJG-UHFFFAOYSA-N 3-[(2-chloro-3,6-difluorophenyl)methoxy]-5-pyrimidin-5-ylpyridin-2-amine Chemical compound NC1=NC=C(C=2C=NC=NC=2)C=C1OCC1=C(F)C=CC(F)=C1Cl VQQDCDDYVNCSJG-UHFFFAOYSA-N 0.000 claims 1
• GDECLRLFRGUYHM-UHFFFAOYSA-N 3-[(2-chloro-6-fluoro-3-methylphenyl)methoxy]-5-phenylpyridin-2-amine Chemical compound CC1=CC=C(F)C(COC=2C(=NC=C(C=2)C=2C=CC=CC=2)N)=C1Cl GDECLRLFRGUYHM-UHFFFAOYSA-N 0.000 claims 1
• DIICUSHOFRGCHG-UHFFFAOYSA-N 3-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]-5-(1h-indol-5-yl)pyridin-2-amine Chemical compound C=1C(C=2C=C3C=CNC3=CC=2)=CN=C(N)C=1OC(C)C1=C(Cl)C=CC(F)=C1Cl DIICUSHOFRGCHG-UHFFFAOYSA-N 0.000 claims 1
• VTOQQRYPFKINSB-UHFFFAOYSA-N 3-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]-5-(1h-pyrazol-4-yl)pyridin-2-amine Chemical compound ClC=1C=CC(F)=C(Cl)C=1C(C)OC(C(=NC=1)N)=CC=1C=1C=NNC=1 VTOQQRYPFKINSB-UHFFFAOYSA-N 0.000 claims 1
• COWLCGJSUMZAAM-UHFFFAOYSA-N 3-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]-5-(2,4-dimethoxyphenyl)pyridin-2-amine Chemical compound COC1=CC(OC)=CC=C1C1=CN=C(N)C(OC(C)C=2C(=C(F)C=CC=2Cl)Cl)=C1 COWLCGJSUMZAAM-UHFFFAOYSA-N 0.000 claims 1
• WIHZGQGWXHMGGS-UHFFFAOYSA-N 3-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]-5-[1-(2-pyrrolidin-1-ylethyl)pyrazol-4-yl]pyridin-2-amine Chemical compound ClC=1C=CC(F)=C(Cl)C=1C(C)OC(C(=NC=1)N)=CC=1C(=C1)C=NN1CCN1CCCC1 WIHZGQGWXHMGGS-UHFFFAOYSA-N 0.000 claims 1
• FMGAYBVWLXVTPO-UHFFFAOYSA-N 3-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]-5-[3-(dimethylamino)prop-1-ynyl]pyridin-2-amine Chemical compound ClC=1C=CC(F)=C(Cl)C=1C(C)OC1=CC(C#CCN(C)C)=CN=C1N FMGAYBVWLXVTPO-UHFFFAOYSA-N 0.000 claims 1
• UNRVFGFQHRXZFH-UHFFFAOYSA-N 3-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]-5-[6-(2-morpholin-4-ylethoxy)pyridin-3-yl]pyridin-2-amine Chemical compound ClC=1C=CC(F)=C(Cl)C=1C(C)OC(C(=NC=1)N)=CC=1C(C=N1)=CC=C1OCCN1CCOCC1 UNRVFGFQHRXZFH-UHFFFAOYSA-N 0.000 claims 1
• JVDSLXIQFSTHRG-UHFFFAOYSA-N 3-[1-(2-chloro-3,6-difluorophenyl)ethoxy]-5-(3-methylbutoxy)pyridin-2-amine Chemical compound CC(C)CCOC1=CN=C(N)C(OC(C)C=2C(=C(F)C=CC=2F)Cl)=C1 JVDSLXIQFSTHRG-UHFFFAOYSA-N 0.000 claims 1
• FVBMMNOAEIZEJL-UHFFFAOYSA-N 3-[1-(2-chloro-3,6-difluorophenyl)ethoxy]-5-(pyridin-4-ylmethoxy)pyridin-2-amine Chemical compound FC=1C=CC(F)=C(Cl)C=1C(C)OC(C(=NC=1)N)=CC=1OCC1=CC=NC=C1 FVBMMNOAEIZEJL-UHFFFAOYSA-N 0.000 claims 1
• XJANXPGIVBNTLT-UHFFFAOYSA-N 3-[1-(2-chloro-3,6-difluorophenyl)ethoxy]-5-[4-(2-morpholin-4-ylethoxy)phenyl]pyridin-2-amine Chemical compound FC=1C=CC(F)=C(Cl)C=1C(C)OC(C(=NC=1)N)=CC=1C(C=C1)=CC=C1OCCN1CCOCC1 XJANXPGIVBNTLT-UHFFFAOYSA-N 0.000 claims 1
• AUXLEGYBIBXELG-UHFFFAOYSA-N 3-[1-(2-chloro-3,6-difluorophenyl)ethoxy]-5-pyridin-2-ylpyridin-2-amine Chemical compound FC=1C=CC(F)=C(Cl)C=1C(C)OC(C(=NC=1)N)=CC=1C1=CC=CC=N1 AUXLEGYBIBXELG-UHFFFAOYSA-N 0.000 claims 1
• JULDPQKCXRFFMR-UHFFFAOYSA-N 3-[1-(2-chloro-3,6-difluorophenyl)ethoxy]-5-pyrimidin-5-ylpyridin-2-amine Chemical compound FC=1C=CC(F)=C(Cl)C=1C(C)OC(C(=NC=1)N)=CC=1C1=CN=CN=C1 JULDPQKCXRFFMR-UHFFFAOYSA-N 0.000 claims 1
• SPOBHCJWTFGAGN-UHFFFAOYSA-N 3-[1-(2-chloro-3-fluorophenyl)ethoxy]-5-[4-(2-pyrrolidin-1-ylethoxy)phenyl]pyridin-2-amine Chemical compound C=1C=CC(F)=C(Cl)C=1C(C)OC(C(=NC=1)N)=CC=1C(C=C1)=CC=C1OCCN1CCCC1 SPOBHCJWTFGAGN-UHFFFAOYSA-N 0.000 claims 1
• RTPJEYHUQJHWOQ-UHFFFAOYSA-N 3-[5-amino-6-[(2-chloro-3,6-difluorophenyl)methoxy]pyrazin-2-yl]benzoic acid Chemical compound NC1=NC=C(C=2C=C(C=CC=2)C(O)=O)N=C1OCC1=C(F)C=CC(F)=C1Cl RTPJEYHUQJHWOQ-UHFFFAOYSA-N 0.000 claims 1
• HLVNBISDFYQDTC-PKHIMPSTSA-N 3-[5-amino-6-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]pyrazin-2-yl]-n-[(2s)-2-hydroxy-3-morpholin-4-ylpropyl]benzamide Chemical compound C([C@@H](O)CNC(=O)C=1C=CC=C(C=1)C=1N=C(C(=NC=1)N)OC(C)C=1C(=C(F)C=CC=1Cl)Cl)N1CCOCC1 HLVNBISDFYQDTC-PKHIMPSTSA-N 0.000 claims 1
• JSAOORPOJFXWQY-UHFFFAOYSA-N 3-[5-amino-6-[1-(2,6-dichlorophenyl)ethoxy]pyrazin-2-yl]-n-(1-methylpiperidin-4-yl)benzamide Chemical compound ClC=1C=CC=C(Cl)C=1C(C)OC(C(=NC=1)N)=NC=1C(C=1)=CC=CC=1C(=O)NC1CCN(C)CC1 JSAOORPOJFXWQY-UHFFFAOYSA-N 0.000 claims 1
• XJMUVFHQFXYBBT-UHFFFAOYSA-N 3-[5-amino-6-[1-(2,6-dichlorophenyl)ethoxy]pyrazin-2-yl]benzoic acid Chemical compound ClC=1C=CC=C(Cl)C=1C(C)OC(C(=NC=1)N)=NC=1C1=CC=CC(C(O)=O)=C1 XJMUVFHQFXYBBT-UHFFFAOYSA-N 0.000 claims 1
• IBHGKBMGNRICGM-UHFFFAOYSA-N 3-[5-amino-6-[1-(2-chloro-3,6-difluorophenyl)ethoxy]pyrazin-2-yl]-n-(3-pyrrolidin-1-ylpropyl)benzamide Chemical compound FC=1C=CC(F)=C(Cl)C=1C(C)OC(C(=NC=1)N)=NC=1C(C=1)=CC=CC=1C(=O)NCCCN1CCCC1 IBHGKBMGNRICGM-UHFFFAOYSA-N 0.000 claims 1
• OLPPDIXVDCIGBQ-UHFFFAOYSA-N 3-[6-amino-5-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]pyridin-3-yl]-n-(1-methylpiperidin-4-yl)benzamide Chemical compound ClC=1C=CC(F)=C(Cl)C=1C(C)OC(C(=NC=1)N)=CC=1C(C=1)=CC=CC=1C(=O)NC1CCN(C)CC1 OLPPDIXVDCIGBQ-UHFFFAOYSA-N 0.000 claims 1
• RFQBCQQPOAXBLK-UHFFFAOYSA-N 3-[6-amino-5-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]pyridin-3-yl]-n-(2-pyrrolidin-1-ylethyl)benzamide Chemical compound ClC=1C=CC(F)=C(Cl)C=1C(C)OC(C(=NC=1)N)=CC=1C(C=1)=CC=CC=1C(=O)NCCN1CCCC1 RFQBCQQPOAXBLK-UHFFFAOYSA-N 0.000 claims 1
• BAKHDCZFCOFSNV-UHFFFAOYSA-N 3-[6-amino-5-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]pyridin-3-yl]phenol Chemical compound ClC=1C=CC(F)=C(Cl)C=1C(C)OC(C(=NC=1)N)=CC=1C1=CC=CC(O)=C1 BAKHDCZFCOFSNV-UHFFFAOYSA-N 0.000 claims 1
• JFHVYKSDKWXQOP-UHFFFAOYSA-N 3-[6-amino-5-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]pyridin-3-yl]prop-2-ynylurea Chemical compound ClC=1C=CC(F)=C(Cl)C=1C(C)OC1=CC(C#CCNC(N)=O)=CN=C1N JFHVYKSDKWXQOP-UHFFFAOYSA-N 0.000 claims 1
• OARAKRNRZXGMIZ-UHFFFAOYSA-N 3-[6-amino-5-[1-(2,6-dichlorophenyl)ethoxy]pyridin-3-yl]-n-(2-morpholin-4-ylethyl)benzamide Chemical compound ClC=1C=CC=C(Cl)C=1C(C)OC(C(=NC=1)N)=CC=1C(C=1)=CC=CC=1C(=O)NCCN1CCOCC1 OARAKRNRZXGMIZ-UHFFFAOYSA-N 0.000 claims 1
• NBWOYVLVBPOSNK-UHFFFAOYSA-N 3-[6-amino-5-[1-(2,6-dichlorophenyl)ethoxy]pyridin-3-yl]-n-(3-pyrrolidin-1-ylpropyl)benzamide Chemical compound ClC=1C=CC=C(Cl)C=1C(C)OC(C(=NC=1)N)=CC=1C(C=1)=CC=CC=1C(=O)NCCCN1CCCC1 NBWOYVLVBPOSNK-UHFFFAOYSA-N 0.000 claims 1
• SKBFHGFPIREMQA-UHFFFAOYSA-N 3-[6-amino-5-[1-(2,6-dichlorophenyl)ethoxy]pyridin-3-yl]benzoic acid Chemical compound ClC=1C=CC=C(Cl)C=1C(C)OC(C(=NC=1)N)=CC=1C1=CC=CC(C(O)=O)=C1 SKBFHGFPIREMQA-UHFFFAOYSA-N 0.000 claims 1
• YEFHRENAXUKCNL-UHFFFAOYSA-N 3-[6-amino-5-[1-(2-chloro-3,6-difluorophenyl)ethoxy]pyridin-3-yl]-n-(2-pyrrolidin-1-ylethyl)benzamide Chemical compound FC=1C=CC(F)=C(Cl)C=1C(C)OC(C(=NC=1)N)=CC=1C(C=1)=CC=CC=1C(=O)NCCN1CCCC1 YEFHRENAXUKCNL-UHFFFAOYSA-N 0.000 claims 1
• QBXSJRUVDVDJAV-UHFFFAOYSA-N 4-(6-amino-5-phenylmethoxypyridin-3-yl)phenol Chemical compound NC1=NC=C(C=2C=CC(O)=CC=2)C=C1OCC1=CC=CC=C1 QBXSJRUVDVDJAV-UHFFFAOYSA-N 0.000 claims 1
• WTTPZQJDKCHNMB-UHFFFAOYSA-N 4-[5-amino-6-[(2,6-dichlorophenyl)methoxy]pyrazin-2-yl]benzoic acid Chemical compound NC1=NC=C(C=2C=CC(=CC=2)C(O)=O)N=C1OCC1=C(Cl)C=CC=C1Cl WTTPZQJDKCHNMB-UHFFFAOYSA-N 0.000 claims 1
• MSNVMXDYPAWLNE-UHFFFAOYSA-N 4-[5-amino-6-[(2-chloro-3,6-difluorophenyl)methoxy]pyrazin-2-yl]-n-(2-pyrrolidin-1-ylethyl)benzamide Chemical compound NC1=NC=C(C=2C=CC(=CC=2)C(=O)NCCN2CCCC2)N=C1OCC1=C(F)C=CC(F)=C1Cl MSNVMXDYPAWLNE-UHFFFAOYSA-N 0.000 claims 1
• JJUFWJNQSBGKHR-UHFFFAOYSA-N 4-[5-amino-6-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]pyrazin-2-yl]-n-(1-methylpiperidin-4-yl)benzamide Chemical compound ClC=1C=CC(F)=C(Cl)C=1C(C)OC(C(=NC=1)N)=NC=1C(C=C1)=CC=C1C(=O)NC1CCN(C)CC1 JJUFWJNQSBGKHR-UHFFFAOYSA-N 0.000 claims 1
• HHJFOJPCRJKCGP-UHFFFAOYSA-N 4-[5-amino-6-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]pyrazin-2-yl]-n-(2-morpholin-4-ylethyl)benzamide Chemical compound ClC=1C=CC(F)=C(Cl)C=1C(C)OC(C(=NC=1)N)=NC=1C(C=C1)=CC=C1C(=O)NCCN1CCOCC1 HHJFOJPCRJKCGP-UHFFFAOYSA-N 0.000 claims 1
• BBWUZEKKUAEGHW-KPMSDPLLSA-N 4-[5-amino-6-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]pyrazin-2-yl]-n-[(2r)-2-hydroxy-3-morpholin-4-ylpropyl]benzamide Chemical compound C([C@H](O)CNC(=O)C1=CC=C(C=C1)C=1N=C(C(=NC=1)N)OC(C)C=1C(=C(F)C=CC=1Cl)Cl)N1CCOCC1 BBWUZEKKUAEGHW-KPMSDPLLSA-N 0.000 claims 1
• DYCFNCARNPWXNS-UHFFFAOYSA-N 4-[5-amino-6-[1-(2,6-dichlorophenyl)ethoxy]pyrazin-2-yl]-n-(3-pyrrolidin-1-ylpropyl)benzamide Chemical compound ClC=1C=CC=C(Cl)C=1C(C)OC(C(=NC=1)N)=NC=1C(C=C1)=CC=C1C(=O)NCCCN1CCCC1 DYCFNCARNPWXNS-UHFFFAOYSA-N 0.000 claims 1
• JCKLWMWFEGAPJZ-UHFFFAOYSA-N 4-[5-amino-6-[1-(2-chloro-3,6-difluorophenyl)ethoxy]pyrazin-2-yl]-n-(1-methylpiperidin-4-yl)benzamide Chemical compound FC=1C=CC(F)=C(Cl)C=1C(C)OC(C(=NC=1)N)=NC=1C(C=C1)=CC=C1C(=O)NC1CCN(C)CC1 JCKLWMWFEGAPJZ-UHFFFAOYSA-N 0.000 claims 1
• XPAZDNGMBGRTAQ-UHFFFAOYSA-N 4-[6-amino-5-[(2,6-dichlorophenyl)methoxy]pyridin-3-yl]-n-(2-hydroxy-3-pyrrolidin-1-ylpropyl)-n-methylbenzamide Chemical compound C=1C=C(C=2C=C(OCC=3C(=CC=CC=3Cl)Cl)C(N)=NC=2)C=CC=1C(=O)N(C)CC(O)CN1CCCC1 XPAZDNGMBGRTAQ-UHFFFAOYSA-N 0.000 claims 1
• LBRKAUPZKJQDQN-UHFFFAOYSA-N 4-[6-amino-5-[(2,6-dichlorophenyl)methoxy]pyridin-3-yl]-n-[2-(diethylamino)ethyl]benzamide Chemical compound C1=CC(C(=O)NCCN(CC)CC)=CC=C1C1=CN=C(N)C(OCC=2C(=CC=CC=2Cl)Cl)=C1 LBRKAUPZKJQDQN-UHFFFAOYSA-N 0.000 claims 1
• UJKMOESTJDYVPG-UHFFFAOYSA-N 4-[6-amino-5-[(2,6-dichlorophenyl)methoxy]pyridin-3-yl]-n-[3-(diethylamino)propyl]benzamide Chemical compound C1=CC(C(=O)NCCCN(CC)CC)=CC=C1C1=CN=C(N)C(OCC=2C(=CC=CC=2Cl)Cl)=C1 UJKMOESTJDYVPG-UHFFFAOYSA-N 0.000 claims 1
• XFHKZERSWQSOML-UHFFFAOYSA-N 4-[6-amino-5-[(2,6-difluorophenyl)methoxy]pyridin-3-yl]benzoic acid Chemical compound NC1=NC=C(C=2C=CC(=CC=2)C(O)=O)C=C1OCC1=C(F)C=CC=C1F XFHKZERSWQSOML-UHFFFAOYSA-N 0.000 claims 1
• DZCRAQUWHHVPCL-UHFFFAOYSA-N 4-[6-amino-5-[(2-chloro-3,6-difluorophenyl)methoxy]pyridin-3-yl]benzoic acid Chemical compound NC1=NC=C(C=2C=CC(=CC=2)C(O)=O)C=C1OCC1=C(F)C=CC(F)=C1Cl DZCRAQUWHHVPCL-UHFFFAOYSA-N 0.000 claims 1
• GJCARVIZAHETSG-UHFFFAOYSA-N 4-[6-amino-5-[(2-chloro-4-fluorophenyl)methoxy]pyridin-3-yl]benzoic acid Chemical compound NC1=NC=C(C=2C=CC(=CC=2)C(O)=O)C=C1OCC1=CC=C(F)C=C1Cl GJCARVIZAHETSG-UHFFFAOYSA-N 0.000 claims 1
• MAQONCGTVMTWJE-UHFFFAOYSA-N 4-[6-amino-5-[(2-chloro-6-fluorophenyl)methoxy]pyridin-3-yl]phenol Chemical compound NC1=NC=C(C=2C=CC(O)=CC=2)C=C1OCC1=C(F)C=CC=C1Cl MAQONCGTVMTWJE-UHFFFAOYSA-N 0.000 claims 1
• KVUQQKAJQLPTGP-UHFFFAOYSA-N 4-[6-amino-5-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]pyridin-3-yl]-n-(3-pyrrolidin-1-ylpropyl)benzamide Chemical compound ClC=1C=CC(F)=C(Cl)C=1C(C)OC(C(=NC=1)N)=CC=1C(C=C1)=CC=C1C(=O)NCCCN1CCCC1 KVUQQKAJQLPTGP-UHFFFAOYSA-N 0.000 claims 1
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