NZ541861A - Aminoheteroaryl compounds as protein kinase inhibitors - Google Patents

Info

Publication number

NZ541861A

NZ541861A NZ541861A NZ54186104A NZ541861A NZ 541861 A NZ541861 A NZ 541861A NZ 541861 A NZ541861 A NZ 541861A NZ 54186104 A NZ54186104 A NZ 54186104A NZ 541861 A NZ541861 A NZ 541861A

Authority

NZ

New Zealand

Prior art keywords

phenyl

amino

pyridin

ethoxy

dichloro

Prior art date

2003-02-26

Links

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• 125000005214 aminoheteroaryl group Chemical group 0.000 title description 2
• 229940045988 antineoplastic drug protein kinase inhibitors Drugs 0.000 title description 2
• 239000003909 protein kinase inhibitor Substances 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 287
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 74
• 201000011510 cancer Diseases 0.000 claims abstract description 45
• 125000001072 heteroaryl group Chemical group 0.000 claims description 215
• 125000003118 aryl group Chemical group 0.000 claims description 205
• 229910052739 hydrogen Inorganic materials 0.000 claims description 153
• 239000001257 hydrogen Substances 0.000 claims description 153
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 144
• 125000000217 alkyl group Chemical group 0.000 claims description 117
• -1 thiopene Natural products 0.000 claims description 103
• 239000000203 mixture Substances 0.000 claims description 102
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 98
• OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 94
• 229910052736 halogen Inorganic materials 0.000 claims description 90
• 150000002367 halogens Chemical group 0.000 claims description 82
• 150000003839 salts Chemical class 0.000 claims description 74
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 64
• 125000000304 alkynyl group Chemical group 0.000 claims description 61
• 125000003342 alkenyl group Chemical group 0.000 claims description 60
• 229910052757 nitrogen Inorganic materials 0.000 claims description 49
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 48
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 46
• 150000002431 hydrogen Chemical group 0.000 claims description 43
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 40
• GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 40
• KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 34
• YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 33
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 33
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 32
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 32
• 239000005711 Benzoic acid Substances 0.000 claims description 31
• 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 claims description 30
• 239000002253 acid Substances 0.000 claims description 29
• 239000012453 solvate Substances 0.000 claims description 29
• 125000000623 heterocyclic group Chemical group 0.000 claims description 24
• QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 22
• 125000005843 halogen group Chemical group 0.000 claims description 22
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 21
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 20
• 150000004677 hydrates Chemical class 0.000 claims description 20
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 20
• 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 17
• PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 17
• 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 17
• JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 16
• BVOMRRWJQOJMPA-UHFFFAOYSA-N 1,2,3-trithiane Chemical compound C1CSSSC1 BVOMRRWJQOJMPA-UHFFFAOYSA-N 0.000 claims description 16
• CXWGKAYMVASWDQ-UHFFFAOYSA-N 1,2-dithiane Chemical compound C1CCSSC1 CXWGKAYMVASWDQ-UHFFFAOYSA-N 0.000 claims description 16
• WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims description 16
• RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical compound C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 claims description 16
• MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 claims description 16
• WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 claims description 16
• ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 16
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 16
• FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 16
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 16
• LOZWAPSEEHRYPG-UHFFFAOYSA-N dithiane Natural products C1CSCCS1 LOZWAPSEEHRYPG-UHFFFAOYSA-N 0.000 claims description 16
• 239000003814 drug Substances 0.000 claims description 16
• MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 claims description 16
• 239000003112 inhibitor Substances 0.000 claims description 16
• ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims description 16
• CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 16
• WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 16
• USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 claims description 16
• PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 16
• ZVJHJDDKYZXRJI-UHFFFAOYSA-N pyrroline Natural products C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 claims description 16
• BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 16
• 150000003852 triazoles Chemical class 0.000 claims description 16
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 15
• 125000004429 atom Chemical group 0.000 claims description 15
• 125000005842 heteroatom Chemical group 0.000 claims description 15
• DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 claims description 15
• 229910052717 sulfur Inorganic materials 0.000 claims description 15
• VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims description 15
• 229910052760 oxygen Inorganic materials 0.000 claims description 14
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 13
• 125000003545 alkoxy group Chemical group 0.000 claims description 12
• CFAFEJHONLMPQY-UHFFFAOYSA-N beta-Dimethylamino-aethan-alpha-sulfonsaeure Natural products CN(C)CCS(O)(=O)=O CFAFEJHONLMPQY-UHFFFAOYSA-N 0.000 claims description 12
• 229910052799 carbon Inorganic materials 0.000 claims description 12
• 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 12
• 206010006187 Breast cancer Diseases 0.000 claims description 11
• 208000026310 Breast neoplasm Diseases 0.000 claims description 11
• 230000002159 abnormal effect Effects 0.000 claims description 11
• 239000004202 carbamide Substances 0.000 claims description 11
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
• 230000010261 cell growth Effects 0.000 claims description 10
• 125000001424 substituent group Chemical group 0.000 claims description 10
• 229930192474 thiophene Natural products 0.000 claims description 10
• OIXSOQOJISAETD-UHFFFAOYSA-N 2-(diethylamino)ethanesulfonic acid Chemical compound CCN(CC)CCS(O)(=O)=O OIXSOQOJISAETD-UHFFFAOYSA-N 0.000 claims description 9
• 208000020816 lung neoplasm Diseases 0.000 claims description 9
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 8
• KNWWGBNAUNTSRV-UHFFFAOYSA-N 4-methylpiperazine-1-carboxylic acid Chemical compound CN1CCN(C(O)=O)CC1 KNWWGBNAUNTSRV-UHFFFAOYSA-N 0.000 claims description 8
• 206010009944 Colon cancer Diseases 0.000 claims description 8
• 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 8
• 201000005202 lung cancer Diseases 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 7
• SXGZJKUKBWWHRA-UHFFFAOYSA-N 2-(N-morpholiniumyl)ethanesulfonate Chemical compound [O-]S(=O)(=O)CC[NH+]1CCOCC1 SXGZJKUKBWWHRA-UHFFFAOYSA-N 0.000 claims description 7
• 206010033128 Ovarian cancer Diseases 0.000 claims description 7
• 206010061535 Ovarian neoplasm Diseases 0.000 claims description 7
• 239000002246 antineoplastic agent Substances 0.000 claims description 7
• 239000003102 growth factor Substances 0.000 claims description 7
• 150000004885 piperazines Chemical class 0.000 claims description 7
• 238000002360 preparation method Methods 0.000 claims description 7
• 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 6
• KTZFIQVZRIPKSY-UHFFFAOYSA-N 2-(cyclopropylmethylamino)ethanesulfonic acid Chemical compound OS(=O)(=O)CCNCC1CC1 KTZFIQVZRIPKSY-UHFFFAOYSA-N 0.000 claims description 6
• 208000031261 Acute myeloid leukaemia Diseases 0.000 claims description 6
• 208000017604 Hodgkin disease Diseases 0.000 claims description 6
• 208000010747 Hodgkins lymphoma Diseases 0.000 claims description 6
• 206010060862 Prostate cancer Diseases 0.000 claims description 6
• 206010039491 Sarcoma Diseases 0.000 claims description 6
• 208000007097 Urinary Bladder Neoplasms 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
• WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 claims description 6
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
• 208000008443 pancreatic carcinoma Diseases 0.000 claims description 6
• 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims description 5
• IVJULNTWOMZJSH-UHFFFAOYSA-N 2-(cyclopropylamino)ethanesulfonic acid Chemical compound OS(=O)(=O)CCNC1CC1 IVJULNTWOMZJSH-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
• 125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 claims description 5
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 5
• 241000124008 Mammalia Species 0.000 claims description 5
• 208000033776 Myeloid Acute Leukemia Diseases 0.000 claims description 5
• 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 5
• 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 5
• 208000005718 Stomach Neoplasms Diseases 0.000 claims description 5
• 206010017758 gastric cancer Diseases 0.000 claims description 5
• 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 5
• 201000011549 stomach cancer Diseases 0.000 claims description 5
• 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
• YSFZEZFZXVPKDS-UHFFFAOYSA-N 2-pyrrolidin-1-ylethanesulfonic acid Chemical compound OS(=O)(=O)CCN1CCCC1 YSFZEZFZXVPKDS-UHFFFAOYSA-N 0.000 claims description 4
• 102000004190 Enzymes Human genes 0.000 claims description 4
• 108090000790 Enzymes Proteins 0.000 claims description 4
• 208000024770 Thyroid neoplasm Diseases 0.000 claims description 4
• 210000003169 central nervous system Anatomy 0.000 claims description 4
• 208000029742 colonic neoplasm Diseases 0.000 claims description 4
• 229940088598 enzyme Drugs 0.000 claims description 4
• 201000002528 pancreatic cancer Diseases 0.000 claims description 4
• JPAPXUHOEPKQPB-SECBINFHSA-N (2r)-2-(pyrrolidin-1-ylmethyl)pyrrolidine-1-carboxylic acid Chemical compound OC(=O)N1CCC[C@@H]1CN1CCCC1 JPAPXUHOEPKQPB-SECBINFHSA-N 0.000 claims description 3
• 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 3
• 206010000830 Acute leukaemia Diseases 0.000 claims description 3
• 206010005949 Bone cancer Diseases 0.000 claims description 3
• 208000018084 Bone neoplasm Diseases 0.000 claims description 3
• 206010006143 Brain stem glioma Diseases 0.000 claims description 3
• 208000017897 Carcinoma of esophagus Diseases 0.000 claims description 3
• 206010007953 Central nervous system lymphoma Diseases 0.000 claims description 3
• 208000001333 Colorectal Neoplasms Diseases 0.000 claims description 3
• 208000000461 Esophageal Neoplasms Diseases 0.000 claims description 3
• 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
• 206010061252 Intraocular melanoma Diseases 0.000 claims description 3
• 208000008839 Kidney Neoplasms Diseases 0.000 claims description 3
• 208000000821 Parathyroid Neoplasms Diseases 0.000 claims description 3
• 208000002471 Penile Neoplasms Diseases 0.000 claims description 3
• 208000007913 Pituitary Neoplasms Diseases 0.000 claims description 3
• 208000015634 Rectal Neoplasms Diseases 0.000 claims description 3
• 208000006265 Renal cell carcinoma Diseases 0.000 claims description 3
• 229910020008 S(O) Inorganic materials 0.000 claims description 3
• 208000000453 Skin Neoplasms Diseases 0.000 claims description 3
• 208000023915 Ureteral Neoplasms Diseases 0.000 claims description 3
• 206010046458 Urethral neoplasms Diseases 0.000 claims description 3
• 208000002495 Uterine Neoplasms Diseases 0.000 claims description 3
• 201000005969 Uveal melanoma Diseases 0.000 claims description 3
• 201000003761 Vaginal carcinoma Diseases 0.000 claims description 3
• 208000024447 adrenal gland neoplasm Diseases 0.000 claims description 3
• 125000002723 alicyclic group Chemical group 0.000 claims description 3
• 125000004103 aminoalkyl group Chemical group 0.000 claims description 3
• 208000019065 cervical carcinoma Diseases 0.000 claims description 3
• 208000024207 chronic leukemia Diseases 0.000 claims description 3
• 208000030381 cutaneous melanoma Diseases 0.000 claims description 3
• 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 3
• 210000000750 endocrine system Anatomy 0.000 claims description 3
• 201000001343 fallopian tube carcinoma Diseases 0.000 claims description 3
• 201000002575 ocular melanoma Diseases 0.000 claims description 3
• 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 3
• 125000004193 piperazinyl group Chemical group 0.000 claims description 3
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
• 208000016800 primary central nervous system lymphoma Diseases 0.000 claims description 3
• 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 3
• 206010038038 rectal cancer Diseases 0.000 claims description 3
• 201000001275 rectum cancer Diseases 0.000 claims description 3
• 201000000849 skin cancer Diseases 0.000 claims description 3
• 201000003708 skin melanoma Diseases 0.000 claims description 3
• 210000000813 small intestine Anatomy 0.000 claims description 3
• 210000000626 ureter Anatomy 0.000 claims description 3
• 206010046766 uterine cancer Diseases 0.000 claims description 3
• 208000013013 vulvar carcinoma Diseases 0.000 claims description 3
• YEJNKQPKGUJMMK-UHFFFAOYSA-N 1-[4-[6-amino-5-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]pyridin-3-yl]phenyl]-3-(2-morpholin-4-ylethyl)urea Chemical compound ClC=1C=CC(F)=C(Cl)C=1C(C)OC(C(=NC=1)N)=CC=1C(C=C1)=CC=C1NC(=O)NCCN1CCOCC1 YEJNKQPKGUJMMK-UHFFFAOYSA-N 0.000 claims description 2
• 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 claims description 2
• 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 2
• QQQJLTRFSIJPSW-FBMWCMRBSA-N 2-[4-[6-amino-5-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]pyridin-3-yl]phenoxy]-1-[(3r)-3-hydroxypyrrolidin-1-yl]ethanone Chemical compound ClC=1C=CC(F)=C(Cl)C=1C(C)OC(C(=NC=1)N)=CC=1C(C=C1)=CC=C1OCC(=O)N1CC[C@@H](O)C1 QQQJLTRFSIJPSW-FBMWCMRBSA-N 0.000 claims description 2
• VSPFFUQAUKSOAG-UHFFFAOYSA-N 3-[(2,6-dichlorophenyl)methoxy]-5-(1h-indol-4-yl)pyridin-2-amine Chemical compound NC1=NC=C(C=2C=3C=CNC=3C=CC=2)C=C1OCC1=C(Cl)C=CC=C1Cl VSPFFUQAUKSOAG-UHFFFAOYSA-N 0.000 claims description 2
• SGOZCJNQGFJGQH-UHFFFAOYSA-N 3-[(2,6-dichlorophenyl)methoxy]-5-(1h-pyrrol-2-yl)pyridin-2-amine Chemical compound NC1=NC=C(C=2NC=CC=2)C=C1OCC1=C(Cl)C=CC=C1Cl SGOZCJNQGFJGQH-UHFFFAOYSA-N 0.000 claims description 2
• WNCKLKNMFPZRLF-UHFFFAOYSA-N 3-[(2,6-dichlorophenyl)methoxy]-5-(2-phenylmethoxyphenyl)pyridin-2-amine Chemical compound NC1=NC=C(C=2C(=CC=CC=2)OCC=2C=CC=CC=2)C=C1OCC1=C(Cl)C=CC=C1Cl WNCKLKNMFPZRLF-UHFFFAOYSA-N 0.000 claims description 2
• 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 description 2
• AMOXCRKUHPHMAG-UHFFFAOYSA-N 3-[(2,6-dichlorophenyl)methoxy]-5-(4-fluorophenyl)pyridin-2-amine Chemical compound NC1=NC=C(C=2C=CC(F)=CC=2)C=C1OCC1=C(Cl)C=CC=C1Cl AMOXCRKUHPHMAG-UHFFFAOYSA-N 0.000 claims description 2
• RUZRWYSCYNHZAY-UHFFFAOYSA-N 3-[(2,6-dichlorophenyl)methoxy]-5-(4-methylthiophen-2-yl)pyridin-2-amine Chemical compound CC1=CSC(C=2C=C(OCC=3C(=CC=CC=3Cl)Cl)C(N)=NC=2)=C1 RUZRWYSCYNHZAY-UHFFFAOYSA-N 0.000 claims description 2
• AGFOYFSAGDJAJW-UHFFFAOYSA-N 3-[(2,6-dichlorophenyl)methoxy]-5-[2-(trifluoromethoxy)phenyl]pyridin-2-amine Chemical compound NC1=NC=C(C=2C(=CC=CC=2)OC(F)(F)F)C=C1OCC1=C(Cl)C=CC=C1Cl AGFOYFSAGDJAJW-UHFFFAOYSA-N 0.000 claims description 2
• SWSODYAMDICARQ-UHFFFAOYSA-N 3-[(2,6-dichlorophenyl)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(Cl)C=CC=C1Cl SWSODYAMDICARQ-UHFFFAOYSA-N 0.000 claims description 2
• 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 description 2
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• BQIUJAVPWCTWFY-INIZCTEOSA-N [4-[5-amino-6-[(2-chloro-3,6-difluorophenyl)methoxy]pyrazin-2-yl]phenyl]-[(3s)-3-(dimethylamino)pyrrolidin-1-yl]methanone Chemical compound C1[C@@H](N(C)C)CCN1C(=O)C1=CC=C(C=2N=C(OCC=3C(=C(F)C=CC=3F)Cl)C(N)=NC=2)C=C1 BQIUJAVPWCTWFY-INIZCTEOSA-N 0.000 claims 1
• AHQDAPVWQUORBP-AWEZNQCLSA-N [4-[5-amino-6-[(2-chloro-3,6-difluorophenyl)methoxy]pyrazin-2-yl]phenyl]-[(3s)-3-aminopyrrolidin-1-yl]methanone Chemical compound C1[C@@H](N)CCN1C(=O)C1=CC=C(C=2N=C(OCC=3C(=C(F)C=CC=3F)Cl)C(N)=NC=2)C=C1 AHQDAPVWQUORBP-AWEZNQCLSA-N 0.000 claims 1
• KORDDKAJGCSZEW-UHFFFAOYSA-N [4-[5-amino-6-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]pyrazin-2-yl]phenyl]-(4-pyrrolidin-1-ylpiperidin-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)CCC1N1CCCC1 KORDDKAJGCSZEW-UHFFFAOYSA-N 0.000 claims 1
• OIQTXMSJDFKWNS-OZBJMMHXSA-N [4-[5-amino-6-[1-(2,6-dichloro-3-fluorophenyl)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=1Cl)Cl)N1CCCC1 OIQTXMSJDFKWNS-OZBJMMHXSA-N 0.000 claims 1
• VKJMATRHVWGYMG-YIONKMFJSA-N [4-[5-amino-6-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]pyrazin-2-yl]phenyl]-[(3r,5s)-3,5-dimethylpiperazin-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)N1C[C@H](C)N[C@H](C)C1 VKJMATRHVWGYMG-YIONKMFJSA-N 0.000 claims 1
• PSYYECZBGYXYGV-UHFFFAOYSA-N [4-[5-amino-6-[1-(2,6-dichlorophenyl)ethoxy]pyrazin-2-yl]phenyl]-(4-methylpiperazin-1-yl)methanone Chemical compound ClC=1C=CC=C(Cl)C=1C(C)OC(C(=NC=1)N)=NC=1C(C=C1)=CC=C1C(=O)N1CCN(C)CC1 PSYYECZBGYXYGV-UHFFFAOYSA-N 0.000 claims 1
• MFTVBQFIUXEGEL-BDPMCISCSA-N [4-[5-amino-6-[1-(2,6-dichlorophenyl)ethoxy]pyrazin-2-yl]phenyl]-[(2r)-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(=CC=CC=1Cl)Cl)N1CCCC1 MFTVBQFIUXEGEL-BDPMCISCSA-N 0.000 claims 1
• JWXUIXIOFZYNMF-XYPWUTKMSA-N [4-[5-amino-6-[1-(2,6-dichlorophenyl)ethoxy]pyrazin-2-yl]phenyl]-[(3r,5s)-3,5-dimethylpiperazin-1-yl]methanone Chemical compound ClC=1C=CC=C(Cl)C=1C(C)OC(C(=NC=1)N)=NC=1C(C=C1)=CC=C1C(=O)N1C[C@H](C)N[C@H](C)C1 JWXUIXIOFZYNMF-XYPWUTKMSA-N 0.000 claims 1
• APJRBBAKKKTNSO-GPPWNDLUSA-N [4-[5-amino-6-[1-(2,6-dichlorophenyl)ethoxy]pyrazin-2-yl]phenyl]-[(3s)-3-aminopyrrolidin-1-yl]methanone;hydron;chloride Chemical compound Cl.ClC=1C=CC=C(Cl)C=1C(C)OC(C(=NC=1)N)=NC=1C(C=C1)=CC=C1C(=O)N1CC[C@H](N)C1 APJRBBAKKKTNSO-GPPWNDLUSA-N 0.000 claims 1
• AWXCPGBSMTVIDD-UUSAFJCLSA-N [4-[5-amino-6-[1-(2-chloro-3,6-difluorophenyl)ethoxy]pyrazin-2-yl]phenyl]-[(2r)-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-UUSAFJCLSA-N 0.000 claims 1
• ZOJKTIWXQGFYJX-UHFFFAOYSA-N [4-[5-amino-6-[[3-fluoro-2-(trifluoromethyl)phenyl]methoxy]pyrazin-2-yl]phenyl]-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C1=CC=C(C=2N=C(OCC=3C(=C(F)C=CC=3)C(F)(F)F)C(N)=NC=2)C=C1 ZOJKTIWXQGFYJX-UHFFFAOYSA-N 0.000 claims 1
• BVWRPRQOKZAWJE-NRFANRHFSA-N [4-[5-amino-6-[[3-fluoro-2-(trifluoromethyl)phenyl]methoxy]pyrazin-2-yl]phenyl]-[(2s)-2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl]methanone Chemical compound NC1=NC=C(C=2C=CC(=CC=2)C(=O)N2[C@@H](CCC2)CN2CCCC2)N=C1OCC1=CC=CC(F)=C1C(F)(F)F BVWRPRQOKZAWJE-NRFANRHFSA-N 0.000 claims 1
• BSLGMGJRYVFQCO-UHFFFAOYSA-N [4-[6-amino-5-(cyclohexylmethoxy)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=C1OCC1CCCCC1 BSLGMGJRYVFQCO-UHFFFAOYSA-N 0.000 claims 1
• JBRREMBHYRJXKI-UHFFFAOYSA-N [4-[6-amino-5-[(2,4-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(Cl)=CC=3)Cl)C(N)=NC=2)C=C1 JBRREMBHYRJXKI-UHFFFAOYSA-N 0.000 claims 1
• PITBRTYDMRSIJP-UHFFFAOYSA-N [4-[6-amino-5-[(2,4-dichlorophenyl)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=CC=C(Cl)C=C1Cl PITBRTYDMRSIJP-UHFFFAOYSA-N 0.000 claims 1
• YVIYTPUPRWRKDJ-NRFANRHFSA-N [4-[6-amino-5-[(2,4-dichlorophenyl)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(=CC(Cl)=CC=3)Cl)C(N)=NC=2)C=C1 YVIYTPUPRWRKDJ-NRFANRHFSA-N 0.000 claims 1
• BWKUUUWGIUIIOC-UHFFFAOYSA-N [4-[6-amino-5-[(2,6-dichlorophenyl)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=3Cl)Cl)C(N)=NC=2)C=C1 BWKUUUWGIUIIOC-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• UCHNAKVAQLPLQV-UHFFFAOYSA-N [4-[6-amino-5-[(2,6-difluorophenyl)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=3F)F)C(N)=NC=2)C=C1 UCHNAKVAQLPLQV-UHFFFAOYSA-N 0.000 claims 1
• HKTCVSAVQLQBRP-KRWDZBQOSA-N [4-[6-amino-5-[(2-chloro-6-fluorophenyl)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(=CC=CC=3F)Cl)C(N)=NC=2)C=C1 HKTCVSAVQLQBRP-KRWDZBQOSA-N 0.000 claims 1
• SWJCPVPNVFOEIB-UHFFFAOYSA-N [4-[6-amino-5-[(2-chlorophenyl)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=CC=CC=C1Cl SWJCPVPNVFOEIB-UHFFFAOYSA-N 0.000 claims 1
• MIUQJZIJHGRNHG-NRFANRHFSA-N [4-[6-amino-5-[(2-chlorophenyl)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(=CC=CC=3)Cl)C(N)=NC=2)C=C1 MIUQJZIJHGRNHG-NRFANRHFSA-N 0.000 claims 1
• DOAOMVUAMWDVSU-UHFFFAOYSA-N [4-[6-amino-5-[(2-methylphenyl)methoxy]pyridin-3-yl]phenyl]-(4-pyrrolidin-1-ylpiperidin-1-yl)methanone Chemical compound CC1=CC=CC=C1COC1=CC(C=2C=CC(=CC=2)C(=O)N2CCC(CC2)N2CCCC2)=CN=C1N DOAOMVUAMWDVSU-UHFFFAOYSA-N 0.000 claims 1
• AEHVEIFJNDIFGT-CALCHBBNSA-N [4-[6-amino-5-[(3-fluoro-2-methoxyphenyl)methoxy]pyridin-3-yl]phenyl]-[(3r,5s)-3,5-dimethylpiperazin-1-yl]methanone Chemical compound COC1=C(F)C=CC=C1COC1=CC(C=2C=CC(=CC=2)C(=O)N2C[C@@H](C)N[C@@H](C)C2)=CN=C1N AEHVEIFJNDIFGT-CALCHBBNSA-N 0.000 claims 1
• JMGOJLQRGQIDEJ-KDURUIRLSA-N [4-[6-amino-5-[(3-fluoro-2-propan-2-yloxyphenyl)methoxy]pyridin-3-yl]phenyl]-[(3r,5s)-3,5-dimethylpiperazin-1-yl]methanone Chemical compound CC(C)OC1=C(F)C=CC=C1COC1=CC(C=2C=CC(=CC=2)C(=O)N2C[C@@H](C)N[C@@H](C)C2)=CN=C1N JMGOJLQRGQIDEJ-KDURUIRLSA-N 0.000 claims 1
• XKNINUBHMGWYIV-UHFFFAOYSA-N [4-[6-amino-5-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]pyridin-3-yl]-2-fluorophenyl]-(2,2-dimethylpiperazin-1-yl)methanone Chemical compound ClC=1C=CC(F)=C(Cl)C=1C(C)OC(C(=NC=1)N)=CC=1C(C=C1F)=CC=C1C(=O)N1CCNCC1(C)C XKNINUBHMGWYIV-UHFFFAOYSA-N 0.000 claims 1
• KKZCMUIQONHMRX-UHFFFAOYSA-N [4-[6-amino-5-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]pyridin-3-yl]-3-fluorophenyl]-(2,2-dimethylpiperazin-1-yl)methanone Chemical compound ClC=1C=CC(F)=C(Cl)C=1C(C)OC(C(=NC=1)N)=CC=1C(C(=C1)F)=CC=C1C(=O)N1CCNCC1(C)C KKZCMUIQONHMRX-UHFFFAOYSA-N 0.000 claims 1
• GCHXQZRZNXAOKV-UHFFFAOYSA-N [4-[6-amino-5-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]pyridin-3-yl]phenyl]-(4-methyl-1,4-diazepan-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)N1CCCN(C)CC1 GCHXQZRZNXAOKV-UHFFFAOYSA-N 0.000 claims 1
• GCHURKJETQITJF-UHFFFAOYSA-N [4-[6-amino-5-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]pyridin-3-yl]phenyl]-(4-methylpiperazin-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)N1CCN(C)CC1 GCHURKJETQITJF-UHFFFAOYSA-N 0.000 claims 1
• CDAABCUOKXSPJC-UHFFFAOYSA-N [4-[6-amino-5-[1-(2,6-dichlorophenyl)ethoxy]pyridin-3-yl]phenyl]-(4-pyrrolidin-1-ylpiperidin-1-yl)methanone Chemical compound ClC=1C=CC=C(Cl)C=1C(C)OC(C(=NC=1)N)=CC=1C(C=C1)=CC=C1C(=O)N(CC1)CCC1N1CCCC1 CDAABCUOKXSPJC-UHFFFAOYSA-N 0.000 claims 1
• VZYQNRXUIIMQEQ-XPKAQORNSA-N [4-[6-amino-5-[1-(2,6-dichlorophenyl)ethoxy]pyridin-3-yl]phenyl]-[(3r)-3-aminopyrrolidin-1-yl]methanone Chemical compound ClC=1C=CC=C(Cl)C=1C(C)OC(C(=NC=1)N)=CC=1C(C=C1)=CC=C1C(=O)N1CC[C@@H](N)C1 VZYQNRXUIIMQEQ-XPKAQORNSA-N 0.000 claims 1
• ZQAQQCXBCQPQOX-UHFFFAOYSA-N [4-[6-amino-5-[1-(2-chloro-3,6-difluorophenyl)ethoxy]pyridin-3-yl]phenyl]-(4-methylpiperazin-1-yl)methanone Chemical compound FC=1C=CC(F)=C(Cl)C=1C(C)OC(C(=NC=1)N)=CC=1C(C=C1)=CC=C1C(=O)N1CCN(C)CC1 ZQAQQCXBCQPQOX-UHFFFAOYSA-N 0.000 claims 1
• ZNEJCLADWQQWCE-XYPWUTKMSA-N [4-[6-amino-5-[1-(2-chloro-3,6-difluorophenyl)ethoxy]pyridin-3-yl]phenyl]-[(3r,5s)-3,5-dimethylpiperazin-1-yl]methanone Chemical compound FC=1C=CC(F)=C(Cl)C=1C(C)OC(C(=NC=1)N)=CC=1C(C=C1)=CC=C1C(=O)N1C[C@H](C)N[C@H](C)C1 ZNEJCLADWQQWCE-XYPWUTKMSA-N 0.000 claims 1
• SBOQWEGYCBYIFA-UHFFFAOYSA-N [4-[6-amino-5-[1-(6-chloro-2-fluoro-3-methylphenyl)ethoxy]pyridin-3-yl]phenyl]-(4-pyrrolidin-1-ylpiperidin-1-yl)methanone Chemical compound ClC=1C=CC(C)=C(F)C=1C(C)OC(C(=NC=1)N)=CC=1C(C=C1)=CC=C1C(=O)N(CC1)CCC1N1CCCC1 SBOQWEGYCBYIFA-UHFFFAOYSA-N 0.000 claims 1
• VFSQVZBCUOMKIM-XYPWUTKMSA-N [4-[6-amino-5-[1-[2,6-dichloro-4-(trifluoromethyl)phenyl]ethoxy]pyridin-3-yl]phenyl]-[(3r,5s)-3,5-dimethylpiperazin-1-yl]methanone Chemical compound ClC=1C=C(C(F)(F)F)C=C(Cl)C=1C(C)OC(C(=NC=1)N)=CC=1C(C=C1)=CC=C1C(=O)N1C[C@H](C)N[C@H](C)C1 VFSQVZBCUOMKIM-XYPWUTKMSA-N 0.000 claims 1
• NLSGGEDXODSKPV-UHFFFAOYSA-N [4-[6-amino-5-[1-[2-(trifluoromethyl)phenyl]ethoxy]pyridin-3-yl]phenyl]-(3,5-dimethylpiperazin-1-yl)methanone Chemical compound C=1C=CC=C(C(F)(F)F)C=1C(C)OC(C(=NC=1)N)=CC=1C(C=C1)=CC=C1C(=O)N1CC(C)NC(C)C1 NLSGGEDXODSKPV-UHFFFAOYSA-N 0.000 claims 1
• JVANNZOPMDSARA-LEQGEALCSA-N [4-[6-amino-5-[1-[3-fluoro-2-(trifluoromethyl)phenyl]ethoxy]pyridin-3-yl]phenyl]-[(2r)-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(=C(F)C=CC=1)C(F)(F)F)N1CCCC1 JVANNZOPMDSARA-LEQGEALCSA-N 0.000 claims 1
• JVANNZOPMDSARA-BVHINDKJSA-N [4-[6-amino-5-[1-[3-fluoro-2-(trifluoromethyl)phenyl]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(=C(F)C=CC=1)C(F)(F)F)N1CCCC1 JVANNZOPMDSARA-BVHINDKJSA-N 0.000 claims 1
• IEONEXVCYSBFFT-SJPCQFCGSA-N [4-[6-amino-5-[1-[3-fluoro-2-(trifluoromethyl)phenyl]ethoxy]pyridin-3-yl]phenyl]-[(3r,5s)-3,5-dimethylpiperazin-1-yl]methanone Chemical compound C=1C=CC(F)=C(C(F)(F)F)C=1C(C)OC(C(=NC=1)N)=CC=1C(C=C1)=CC=C1C(=O)N1C[C@H](C)N[C@H](C)C1 IEONEXVCYSBFFT-SJPCQFCGSA-N 0.000 claims 1
• GDAWTQDKSMPLMQ-UHFFFAOYSA-N [4-[6-amino-5-[[3-fluoro-2-(trifluoromethyl)phenyl]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(=C(F)C=CC=3)C(F)(F)F)C(N)=NC=2)C=C1 GDAWTQDKSMPLMQ-UHFFFAOYSA-N 0.000 claims 1
• JMFREZMQIYMKAO-UHFFFAOYSA-N [4-[6-amino-5-[[3-fluoro-2-(trifluoromethyl)phenyl]methoxy]pyridin-3-yl]phenyl]-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C1=CC=C(C=2C=C(OCC=3C(=C(F)C=CC=3)C(F)(F)F)C(N)=NC=2)C=C1 JMFREZMQIYMKAO-UHFFFAOYSA-N 0.000 claims 1
• 238000011260 co-administration Methods 0.000 claims 1
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• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
• ARGHYNJBPLSKRW-UHFFFAOYSA-N methyl 4-[6-amino-5-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]pyridin-3-yl]-3-methylbenzoate Chemical compound CC1=CC(C(=O)OC)=CC=C1C1=CN=C(N)C(OC(C)C=2C(=C(F)C=CC=2Cl)Cl)=C1 ARGHYNJBPLSKRW-UHFFFAOYSA-N 0.000 claims 1
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• SARQPHGVCINWPN-UHFFFAOYSA-N n-[2-(4-acetylpiperazin-1-yl)ethyl]-3-[5-amino-6-[[3-fluoro-2-(trifluoromethyl)phenyl]methoxy]pyrazin-2-yl]benzamide Chemical compound C1CN(C(=O)C)CCN1CCNC(=O)C1=CC=CC(C=2N=C(OCC=3C(=C(F)C=CC=3)C(F)(F)F)C(N)=NC=2)=C1 SARQPHGVCINWPN-UHFFFAOYSA-N 0.000 claims 1
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