BRPI0913031A2 - derivados de quinolina e quinoxalinas como inibidores de proteína tirosina quinase, seus usos e processo de fabricação, bem como composições farmacêuticas e combinação que os compreende - Google Patents

Info

Publication number

BRPI0913031A2

BRPI0913031A2 BRPI0913031A BRPI0913031A2 BR PI0913031 A2 BRPI0913031 A2 BR PI0913031A2 BR PI0913031 A BRPI0913031 A BR PI0913031A BR PI0913031 A2 BRPI0913031 A2 BR PI0913031A2

Authority

BR

Brazil

Prior art keywords

phenyl

quinoxaline

amide

dimethoxy

pyridin

Prior art date

2008-05-23

Links

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• 239000005483 tyrosine kinase inhibitor Substances 0.000 title claims abstract description 5
• 239000008194 pharmaceutical composition Substances 0.000 title claims description 23
• 238000004519 manufacturing process Methods 0.000 title claims description 18
• SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 title abstract description 13
• 125000001567 quinoxalinyl group Chemical class N1=C(C=NC2=CC=CC=C12)* 0.000 title abstract 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 678
• 238000000034 method Methods 0.000 claims abstract description 198
• 150000003839 salts Chemical class 0.000 claims abstract description 106
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 99
• 125000001424 substituent group Chemical group 0.000 claims abstract description 89
• 201000010099 disease Diseases 0.000 claims abstract description 71
• 230000008569 process Effects 0.000 claims abstract description 34
• 239000012453 solvate Substances 0.000 claims abstract description 31
• 102000004022 Protein-Tyrosine Kinases Human genes 0.000 claims abstract description 25
• 108090000412 Protein-Tyrosine Kinases Proteins 0.000 claims abstract description 25
• 230000001404 mediated effect Effects 0.000 claims abstract description 20
• 150000002148 esters Chemical class 0.000 claims abstract description 15
• 239000000825 pharmaceutical preparation Substances 0.000 claims abstract description 4
• 229940127557 pharmaceutical product Drugs 0.000 claims abstract 2
• -1 amino , monosubstituted amino Chemical group 0.000 claims description 333
• 239000002253 acid Substances 0.000 claims description 147
• 125000000217 alkyl group Chemical group 0.000 claims description 113
• 238000011282 treatment Methods 0.000 claims description 55
• 206010028980 Neoplasm Diseases 0.000 claims description 52
• 229910052757 nitrogen Inorganic materials 0.000 claims description 50
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 48
• 229920006395 saturated elastomer Polymers 0.000 claims description 48
• 229910052739 hydrogen Inorganic materials 0.000 claims description 38
• 125000000623 heterocyclic group Chemical group 0.000 claims description 37
• 239000001257 hydrogen Substances 0.000 claims description 37
• 125000003118 aryl group Chemical group 0.000 claims description 36
• 125000001072 heteroaryl group Chemical group 0.000 claims description 35
• 239000003112 inhibitor Substances 0.000 claims description 34
• 125000003545 alkoxy group Chemical group 0.000 claims description 33
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 33
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 31
• 125000006413 ring segment Chemical group 0.000 claims description 28
• 239000003814 drug Substances 0.000 claims description 27
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 27
• 150000001204 N-oxides Chemical class 0.000 claims description 26
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 23
• 108091008794 FGF receptors Proteins 0.000 claims description 21
• 239000003085 diluting agent Substances 0.000 claims description 21
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 18
• 125000003282 alkyl amino group Chemical group 0.000 claims description 17
• 125000005843 halogen group Chemical group 0.000 claims description 17
• 201000011510 cancer Diseases 0.000 claims description 16
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 16
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 15
• QLZNISOPACYKOR-UHFFFAOYSA-N quinoxaline-5-carboxylic acid Chemical compound C1=CN=C2C(C(=O)O)=CC=CC2=N1 QLZNISOPACYKOR-UHFFFAOYSA-N 0.000 claims description 15
• 150000002431 hydrogen Chemical class 0.000 claims description 14
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 14
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 14
• 229910052799 carbon Inorganic materials 0.000 claims description 13
• 229910052736 halogen Inorganic materials 0.000 claims description 13
• 230000002062 proliferating effect Effects 0.000 claims description 13
• 150000002367 halogens Chemical class 0.000 claims description 12
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 12
• PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims description 11
• JVMUJWRLQAYOBW-UHFFFAOYSA-N 8-(2,6-dichloro-3,5-dimethoxyphenyl)quinoxaline-5-carboxylic acid Chemical compound COC1=CC(OC)=C(Cl)C(C=2C3=NC=CN=C3C(C(O)=O)=CC=2)=C1Cl JVMUJWRLQAYOBW-UHFFFAOYSA-N 0.000 claims description 11
• 239000004480 active ingredient Substances 0.000 claims description 11
• 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 11
• 208000026310 Breast neoplasm Diseases 0.000 claims description 10
• 230000001028 anti-proliverative effect Effects 0.000 claims description 10
• 125000001624 naphthyl group Chemical group 0.000 claims description 10
• 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 9
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 9
• 239000003054 catalyst Substances 0.000 claims description 9
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 9
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 9
• 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 8
• 206010006187 Breast cancer Diseases 0.000 claims description 8
• 150000001412 amines Chemical class 0.000 claims description 8
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
• 229940043355 kinase inhibitor Drugs 0.000 claims description 8
• 229940124597 therapeutic agent Drugs 0.000 claims description 8
• 239000003937 drug carrier Substances 0.000 claims description 7
• 125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 claims description 7
• 125000003635 2-dimethylaminoethoxy group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])O* 0.000 claims description 6
• MNJBMPQTXVZMFZ-UHFFFAOYSA-N 5-[(4-ethylpiperazin-1-yl)methyl]pyridin-2-amine Chemical compound C1CN(CC)CCN1CC1=CC=C(N)N=C1 MNJBMPQTXVZMFZ-UHFFFAOYSA-N 0.000 claims description 6
• 102000029749 Microtubule Human genes 0.000 claims description 6
• 108091022875 Microtubule Proteins 0.000 claims description 6
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
• 150000001408 amides Chemical class 0.000 claims description 6
• 125000004429 atom Chemical group 0.000 claims description 6
• 239000002585 base Substances 0.000 claims description 6
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 6
• 210000004688 microtubule Anatomy 0.000 claims description 6
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
• 125000004076 pyridyl group Chemical group 0.000 claims description 6
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 5
• VTQLRKWWLAXZMZ-UHFFFAOYSA-N 5-(diethylaminomethyl)pyridin-2-amine Chemical compound CCN(CC)CC1=CC=C(N)N=C1 VTQLRKWWLAXZMZ-UHFFFAOYSA-N 0.000 claims description 5
• 125000004103 aminoalkyl group Chemical group 0.000 claims description 5
• 229940046836 anti-estrogen Drugs 0.000 claims description 5
• 230000001833 anti-estrogenic effect Effects 0.000 claims description 5
• 239000003886 aromatase inhibitor Substances 0.000 claims description 5
• 239000000328 estrogen antagonist Substances 0.000 claims description 5
• 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 5
• 208000005017 glioblastoma Diseases 0.000 claims description 5
• 125000005842 heteroatom Chemical group 0.000 claims description 5
• 125000002950 monocyclic group Chemical group 0.000 claims description 5
• 125000003107 substituted aryl group Chemical group 0.000 claims description 5
• 229910052717 sulfur Inorganic materials 0.000 claims description 5
• NZTCEWZBMOTKCJ-UHFFFAOYSA-N 6-(4-methylpiperazin-1-yl)pyridin-3-amine Chemical compound C1CN(C)CCN1C1=CC=C(N)C=N1 NZTCEWZBMOTKCJ-UHFFFAOYSA-N 0.000 claims description 4
• 229940122815 Aromatase inhibitor Drugs 0.000 claims description 4
• 229940122361 Bisphosphonate Drugs 0.000 claims description 4
• 206010014733 Endometrial cancer Diseases 0.000 claims description 4
• 206010014759 Endometrial neoplasm Diseases 0.000 claims description 4
• 206010025323 Lymphomas Diseases 0.000 claims description 4
• 208000034578 Multiple myelomas Diseases 0.000 claims description 4
• 206010035226 Plasma cell myeloma Diseases 0.000 claims description 4
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 4
• 230000015572 biosynthetic process Effects 0.000 claims description 4
• 150000004663 bisphosphonates Chemical class 0.000 claims description 4
• 102000052178 fibroblast growth factor receptor activity proteins Human genes 0.000 claims description 4
• 206010073071 hepatocellular carcinoma Diseases 0.000 claims description 4
• 208000014018 liver neoplasm Diseases 0.000 claims description 4
• 239000000463 material Substances 0.000 claims description 4
• 125000002757 morpholinyl group Chemical group 0.000 claims description 4
• 150000003058 platinum compounds Chemical class 0.000 claims description 4
• 239000003909 protein kinase inhibitor Substances 0.000 claims description 4
• 239000011593 sulfur Substances 0.000 claims description 4
• 125000001544 thienyl group Chemical group 0.000 claims description 4
• OMIVCRYZSXDGAB-UHFFFAOYSA-N 1,4-butanediyl Chemical group [CH2]CC[CH2] OMIVCRYZSXDGAB-UHFFFAOYSA-N 0.000 claims description 3
• NLZPNQSVIPUNQS-UHFFFAOYSA-N 8-(2,6-dimethylphenyl)quinoxaline-5-carboxylic acid Chemical compound CC1=CC=CC(C)=C1C1=CC=C(C(O)=O)C2=NC=CN=C12 NLZPNQSVIPUNQS-UHFFFAOYSA-N 0.000 claims description 3
• AAVGQAOOVHWRIG-UHFFFAOYSA-N 8-(2-fluorophenyl)quinoxaline-5-carboxylic acid Chemical compound C12=NC=CN=C2C(C(=O)O)=CC=C1C1=CC=CC=C1F AAVGQAOOVHWRIG-UHFFFAOYSA-N 0.000 claims description 3
• 206010005003 Bladder cancer Diseases 0.000 claims description 3
• 229940124087 DNA topoisomerase II inhibitor Drugs 0.000 claims description 3
• 206010060862 Prostate cancer Diseases 0.000 claims description 3
• 208000000102 Squamous Cell Carcinoma of Head and Neck Diseases 0.000 claims description 3
• 239000000317 Topoisomerase II Inhibitor Substances 0.000 claims description 3
• 239000013543 active substance Substances 0.000 claims description 3
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 3
• 239000002168 alkylating agent Substances 0.000 claims description 3
• 150000001639 boron compounds Chemical class 0.000 claims description 3
• 125000005620 boronic acid group Chemical group 0.000 claims description 3
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 3
• 125000002883 imidazolyl group Chemical group 0.000 claims description 3
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
• 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
• 125000004043 oxo group Chemical group O=* 0.000 claims description 3
• 208000008443 pancreatic carcinoma Diseases 0.000 claims description 3
• 125000004193 piperazinyl group Chemical group 0.000 claims description 3
• 125000003386 piperidinyl group Chemical group 0.000 claims description 3
• 201000001514 prostate carcinoma Diseases 0.000 claims description 3
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 3
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 3
• CUJPFPXNDSIBPG-UHFFFAOYSA-N 1,3-propanediyl Chemical group [CH2]C[CH2] CUJPFPXNDSIBPG-UHFFFAOYSA-N 0.000 claims description 2
• MMQCTXWUZNJUTF-UHFFFAOYSA-N 5-[(4-methylpiperazin-1-yl)methyl]pyridin-2-amine Chemical compound C1CN(C)CCN1CC1=CC=C(N)N=C1 MMQCTXWUZNJUTF-UHFFFAOYSA-N 0.000 claims description 2
• ODGCXWOTVCKKIR-UHFFFAOYSA-N 8-(2-fluoro-3,5-dimethoxyphenyl)quinoxaline-5-carboxylic acid Chemical compound COC1=CC(OC)=C(F)C(C=2C3=NC=CN=C3C(C(O)=O)=CC=2)=C1 ODGCXWOTVCKKIR-UHFFFAOYSA-N 0.000 claims description 2
• CHJBKOUQICYSQO-UHFFFAOYSA-N 8-naphthalen-1-ylquinoxaline-5-carboxylic acid Chemical compound C12=NC=CN=C2C(C(=O)O)=CC=C1C1=CC=CC2=CC=CC=C12 CHJBKOUQICYSQO-UHFFFAOYSA-N 0.000 claims description 2
• 101710199605 Endoribonuclease Proteins 0.000 claims description 2
• 208000007913 Pituitary Neoplasms Diseases 0.000 claims description 2
• 102000014400 SH2 domains Human genes 0.000 claims description 2
• 108050003452 SH2 domains Proteins 0.000 claims description 2
• 101710113029 Serine/threonine-protein kinase Proteins 0.000 claims description 2
• 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims description 2
• 229940100198 alkylating agent Drugs 0.000 claims description 2
• 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 2
• 230000000340 anti-metabolite Effects 0.000 claims description 2
• 229940100197 antimetabolite Drugs 0.000 claims description 2
• 239000002256 antimetabolite Substances 0.000 claims description 2
• 125000002393 azetidinyl group Chemical group 0.000 claims description 2
• 239000000824 cytostatic agent Substances 0.000 claims description 2
• 230000001085 cytostatic effect Effects 0.000 claims description 2
• 231100000433 cytotoxic Toxicity 0.000 claims description 2
• 230000001472 cytotoxic effect Effects 0.000 claims description 2
• 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
• 208000021045 exocrine pancreatic carcinoma Diseases 0.000 claims description 2
• 206010017758 gastric cancer Diseases 0.000 claims description 2
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• 239000003630 growth substance Substances 0.000 claims description 2
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
• 230000003993 interaction Effects 0.000 claims description 2
• 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims description 2
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 2
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 2
• 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 2
• 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 claims description 2
• 108091005981 phosphorylated proteins Proteins 0.000 claims description 2
• 229920000768 polyamine Polymers 0.000 claims description 2
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 2
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
• 201000000498 stomach carcinoma Diseases 0.000 claims description 2
• 201000005112 urinary bladder cancer Diseases 0.000 claims description 2
• UXNYKUAVUQXHDG-UHFFFAOYSA-N 8-(2,6-difluoro-3,5-dimethoxyphenyl)quinoxaline-5-carboxylic acid Chemical compound COC1=CC(OC)=C(F)C(C=2C3=NC=CN=C3C(C(O)=O)=CC=2)=C1F UXNYKUAVUQXHDG-UHFFFAOYSA-N 0.000 claims 6
• NWUOZTZYEOTHEM-UHFFFAOYSA-N 5-(2,6-dichloro-3,5-dimethoxyphenyl)quinoline-8-carboxylic acid Chemical compound COC1=CC(OC)=C(Cl)C(C=2C3=CC=CN=C3C(C(O)=O)=CC=2)=C1Cl NWUOZTZYEOTHEM-UHFFFAOYSA-N 0.000 claims 4
• 125000001309 chloro group Chemical group Cl* 0.000 claims 4
• 125000001153 fluoro group Chemical group F* 0.000 claims 4
• QFUPHFQAVUNDMP-UHFFFAOYSA-N 1-[2-(dimethylamino)ethyl]pyrrol-3-amine Chemical compound CN(C)CCN1C=CC(N)=C1 QFUPHFQAVUNDMP-UHFFFAOYSA-N 0.000 claims 2
• OJEGDZDGQYHZJU-UHFFFAOYSA-N 2-(2,6-difluoro-3,5-dimethoxyphenyl)quinoxaline-5-carboxylic acid Chemical compound FC1=C(C(=C(C=C1OC)OC)F)C1=NC=2C=CC=C(C=2N=C1)C(=O)O OJEGDZDGQYHZJU-UHFFFAOYSA-N 0.000 claims 2
• GBHRYASADXGJBM-UHFFFAOYSA-N 4-[(2-amino-1H-imidazol-5-yl)methyl]piperazin-2-one Chemical compound N1C(N)=NC=C1CN1CC(=O)NCC1 GBHRYASADXGJBM-UHFFFAOYSA-N 0.000 claims 2
• NLDAKFJFRSITDJ-UHFFFAOYSA-N 1-[(2-amino-1H-imidazol-5-yl)methyl]azetidine-3-carbonitrile Chemical compound N1C(N)=NC=C1CN1CC(C#N)C1 NLDAKFJFRSITDJ-UHFFFAOYSA-N 0.000 claims 1
• 101710175516 14 kDa zinc-binding protein Proteins 0.000 claims 1
• RINAGKQFKGSWBK-UHFFFAOYSA-N 2-[(2-amino-1H-imidazol-5-yl)methyl-methylamino]acetonitrile Chemical compound N#CCN(C)CC1=CN=C(N)N1 RINAGKQFKGSWBK-UHFFFAOYSA-N 0.000 claims 1
• MVVNPCDSMLHDFR-UHFFFAOYSA-N 2-[(6-aminopyridin-3-yl)methyl-methylamino]acetamide Chemical compound NC(=O)CN(C)CC1=CC=C(N)N=C1 MVVNPCDSMLHDFR-UHFFFAOYSA-N 0.000 claims 1
• QMVOPFYALSCPRF-UHFFFAOYSA-N 2-[(6-aminopyridin-3-yl)methyl-methylamino]acetamide 8-(2,6-difluoro-3,5-dimethoxyphenyl)quinoxaline-5-carboxylic acid Chemical compound NC(=O)CN(C)CC1=CC=C(N)N=C1.COC1=CC(OC)=C(F)C(C=2C3=NC=CN=C3C(C(O)=O)=CC=2)=C1F QMVOPFYALSCPRF-UHFFFAOYSA-N 0.000 claims 1
• NXHVNCXFBLAXKY-UHFFFAOYSA-N 2-n-methyl-2-n-(1-methylpiperidin-4-yl)pyridine-2,5-diamine Chemical compound C=1C=C(N)C=NC=1N(C)C1CCN(C)CC1 NXHVNCXFBLAXKY-UHFFFAOYSA-N 0.000 claims 1
• PHNDZBFLOPIMSM-UHFFFAOYSA-N 4-morpholin-4-ylaniline Chemical compound C1=CC(N)=CC=C1N1CCOCC1 PHNDZBFLOPIMSM-UHFFFAOYSA-N 0.000 claims 1
• UFQIIMKAJNPQOV-UHFFFAOYSA-N 5-(2,6-dichloro-3,5-dimethoxyphenyl)-n-[5-(piperazin-1-ylmethyl)pyridin-2-yl]quinoline-8-carboxamide Chemical compound COC1=CC(OC)=C(Cl)C(C=2C3=CC=CN=C3C(C(=O)NC=3N=CC(CN4CCNCC4)=CC=3)=CC=2)=C1Cl UFQIIMKAJNPQOV-UHFFFAOYSA-N 0.000 claims 1
• IWUWYFFTFBUXLD-UHFFFAOYSA-N 5-(2-chloro-6-fluoro-3,5-dimethoxyphenyl)quinoline-8-carboxylic acid Chemical compound COC1=CC(OC)=C(Cl)C(C=2C3=CC=CN=C3C(C(O)=O)=CC=2)=C1F IWUWYFFTFBUXLD-UHFFFAOYSA-N 0.000 claims 1
• MVZUMHORLBDOJQ-UHFFFAOYSA-N 5-(imidazol-1-ylmethyl)pyridin-2-amine Chemical compound C1=NC(N)=CC=C1CN1C=NC=C1 MVZUMHORLBDOJQ-UHFFFAOYSA-N 0.000 claims 1
• KZSOCAIRCZPXHG-UHFFFAOYSA-N 5-(piperazin-1-ylmethyl)pyridin-2-amine Chemical compound C1=NC(N)=CC=C1CN1CCNCC1 KZSOCAIRCZPXHG-UHFFFAOYSA-N 0.000 claims 1
• LHOXTPGEHWPRTF-UHFFFAOYSA-N 5-[(1,1-dioxo-1,4-thiazinan-4-yl)methyl]pyridin-2-amine Chemical compound C1=NC(N)=CC=C1CN1CCS(=O)(=O)CC1 LHOXTPGEHWPRTF-UHFFFAOYSA-N 0.000 claims 1
• MIUDDGVLRKBYBV-UHFFFAOYSA-N 5-[(3,3,4-trimethylpiperazin-1-yl)methyl]pyridin-2-amine Chemical compound C1C(C)(C)N(C)CCN1CC1=CC=C(N)N=C1 MIUDDGVLRKBYBV-UHFFFAOYSA-N 0.000 claims 1
• KYMFEWBZMKNMDR-UHFFFAOYSA-N 5-[(4-ethylpiperazin-1-yl)methyl]-1H-imidazol-2-amine Chemical compound C1CN(CC)CCN1CC1=CN=C(N)N1 KYMFEWBZMKNMDR-UHFFFAOYSA-N 0.000 claims 1
• VMCGLQGCFHBQAO-UHFFFAOYSA-N 5-[(dimethylamino)methyl]-1H-imidazol-2-amine Chemical compound CN(C)CC1=CN=C(N)N1 VMCGLQGCFHBQAO-UHFFFAOYSA-N 0.000 claims 1
• TUBDKBIRGSSPNK-UHFFFAOYSA-N 6-(4-ethylpiperazin-1-yl)pyridin-3-amine Chemical compound C1CN(CC)CCN1C1=CC=C(N)C=N1 TUBDKBIRGSSPNK-UHFFFAOYSA-N 0.000 claims 1
• GJDFSLJJAGGJHJ-UHFFFAOYSA-N 6-(diethylaminomethyl)pyridin-3-amine Chemical compound CCN(CC)CC1=CC=C(N)C=N1 GJDFSLJJAGGJHJ-UHFFFAOYSA-N 0.000 claims 1
• PUCKMVDXHCJGDB-UHFFFAOYSA-N 6-(piperazin-1-ylmethyl)pyridin-3-amine Chemical compound N1=CC(N)=CC=C1CN1CCNCC1 PUCKMVDXHCJGDB-UHFFFAOYSA-N 0.000 claims 1
• QTSVCCDELYSMEA-UHFFFAOYSA-N 6-[(2,2,4-trimethylpiperazin-1-yl)methyl]pyridin-3-amine Chemical compound CC1(C)CN(C)CCN1CC1=CC=C(N)C=N1 QTSVCCDELYSMEA-UHFFFAOYSA-N 0.000 claims 1
• XXPNYARYJNXRMH-UHFFFAOYSA-N 6-[(3,3,4-trimethylpiperazin-1-yl)methyl]pyridin-3-amine Chemical compound C1C(C)(C)N(C)CCN1CC1=CC=C(N)C=N1 XXPNYARYJNXRMH-UHFFFAOYSA-N 0.000 claims 1
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• 125000004933 β-carbolinyl group Chemical group C1(=NC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
• 239000002446 δ-tocopherol Substances 0.000 description 1