BG108013A - Заместени аминопроизводни и методи за използването им - Google Patents

Info

Publication number

BG108013A

BG108013A BG108013A BG10801303A BG108013A BG 108013 A BG108013 A BG 108013A BG 108013 A BG108013 A BG 108013A BG 10801303 A BG10801303 A BG 10801303A BG 108013 A BG108013 A BG 108013A

Authority

BG

Bulgaria

Prior art keywords

optionally substituted

substituted

phenyl

alkyl

methyl

Prior art date

2001-01-12

Links

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• Global Dossier
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• 238000000034 method Methods 0.000 title claims abstract description 77
• 150000001412 amines Chemical class 0.000 title abstract description 19
• 150000001875 compounds Chemical class 0.000 claims abstract description 159
• 238000011282 treatment Methods 0.000 claims abstract description 44
• 150000003839 salts Chemical class 0.000 claims abstract description 38
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 37
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 36
• 230000008569 process Effects 0.000 claims abstract description 31
• 201000010099 disease Diseases 0.000 claims abstract description 26
• 230000033115 angiogenesis Effects 0.000 claims abstract description 14
• 201000011510 cancer Diseases 0.000 claims abstract description 13
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 3
• -1 halosulfonyl Chemical group 0.000 claims description 1529
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 298
• 125000000217 alkyl group Chemical group 0.000 claims description 230
• 125000000623 heterocyclic group Chemical group 0.000 claims description 187
• 229910052799 carbon Inorganic materials 0.000 claims description 176
• 125000001424 substituent group Chemical group 0.000 claims description 126
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 122
• 125000003545 alkoxy group Chemical group 0.000 claims description 101
• 125000005843 halogen group Chemical group 0.000 claims description 98
• 229910052757 nitrogen Inorganic materials 0.000 claims description 86
• 229910052739 hydrogen Inorganic materials 0.000 claims description 78
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 77
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 73
• 150000003857 carboxamides Chemical class 0.000 claims description 70
• 125000004076 pyridyl group Chemical group 0.000 claims description 64
• 125000005956 isoquinolyl group Chemical group 0.000 claims description 59
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 59
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 58
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 56
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 54
• 125000004043 oxo group Chemical group O=* 0.000 claims description 53
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 51
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 46
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 46
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 46
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 45
• 125000001072 heteroaryl group Chemical group 0.000 claims description 44
• 125000002883 imidazolyl group Chemical group 0.000 claims description 44
• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 43
• 125000001544 thienyl group Chemical group 0.000 claims description 43
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 40
• 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 39
• 125000001041 indolyl group Chemical group 0.000 claims description 38
• 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 37
• 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 34
• 125000000304 alkynyl group Chemical group 0.000 claims description 33
• 125000001624 naphthyl group Chemical group 0.000 claims description 31
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 29
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 29
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 29
• 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 28
• 125000005493 quinolyl group Chemical group 0.000 claims description 28
• 125000000335 thiazolyl group Chemical group 0.000 claims description 28
• 125000002541 furyl group Chemical group 0.000 claims description 27
• 125000001188 haloalkyl group Chemical group 0.000 claims description 27
• 125000002757 morpholinyl group Chemical group 0.000 claims description 27
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 26
• 239000011570 nicotinamide Substances 0.000 claims description 26
• 229960003966 nicotinamide Drugs 0.000 claims description 26
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 26
• 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 25
• 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 25
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 25
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 24
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 24
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 24
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 24
• 229910052751 metal Inorganic materials 0.000 claims description 24
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 24
• YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 23
• 239000002184 metal Substances 0.000 claims description 23
• DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 22
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 22
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 21
• 229910052760 oxygen Inorganic materials 0.000 claims description 21
• 125000003107 substituted aryl group Chemical group 0.000 claims description 21
• 125000002619 bicyclic group Chemical group 0.000 claims description 20
• 125000006517 heterocyclyl carbonyl group Chemical group 0.000 claims description 20
• 229910052717 sulfur Inorganic materials 0.000 claims description 20
• 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 20
• 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims description 19
• 125000003342 alkenyl group Chemical group 0.000 claims description 19
• 125000003282 alkyl amino group Chemical group 0.000 claims description 19
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 19
• 125000003118 aryl group Chemical group 0.000 claims description 19
• 239000003795 chemical substances by application Substances 0.000 claims description 19
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 19
• 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 18
• 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 18
• 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 17
• 125000004103 aminoalkyl group Chemical group 0.000 claims description 17
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 17
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 16
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 16
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 16
• 125000003386 piperidinyl group Chemical group 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
• 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims description 14
• 235000005152 nicotinamide Nutrition 0.000 claims description 14
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 13
• 125000001153 fluoro group Chemical group F* 0.000 claims description 13
• 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims description 13
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 12
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 12
• 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 12
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 12
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 12
• 125000001113 thiadiazolyl group Chemical group 0.000 claims description 12
• 125000001246 bromo group Chemical group Br* 0.000 claims description 11
• 125000004181 carboxyalkyl group Chemical group 0.000 claims description 11
• 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 claims description 11
• 238000002360 preparation method Methods 0.000 claims description 11
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 11
• 125000005605 benzo group Chemical group 0.000 claims description 10
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 10
• PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 10
• 239000001301 oxygen Substances 0.000 claims description 10
• 125000001425 triazolyl group Chemical group 0.000 claims description 10
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 10
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 9
• 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 9
• UWVCZZTXUMTYKO-UHFFFAOYSA-N 2-(1h-indazol-6-ylamino)pyridine-3-carboxamide Chemical compound NC(=O)C1=CC=CN=C1NC1=CC=C(C=NN2)C2=C1 UWVCZZTXUMTYKO-UHFFFAOYSA-N 0.000 claims description 9
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 9
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
• 239000003814 drug Substances 0.000 claims description 9
• 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 8
• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 8
• 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 claims description 8
• 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 8
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 8
• 108010050904 Interferons Proteins 0.000 claims description 8
• 102000014150 Interferons Human genes 0.000 claims description 8
• 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 8
• 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 8
• 229940079322 interferon Drugs 0.000 claims description 8
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 8
• 125000004193 piperazinyl group Chemical group 0.000 claims description 8
• 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims description 8
• 206010061218 Inflammation Diseases 0.000 claims description 7
• 125000003418 alkyl amino alkoxy group Chemical group 0.000 claims description 7
• 125000002947 alkylene group Chemical group 0.000 claims description 7
• 230000004054 inflammatory process Effects 0.000 claims description 7
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 7
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 6
• ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 claims description 6
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
• 230000035755 proliferation Effects 0.000 claims description 6
• 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 6
• 239000011593 sulfur Substances 0.000 claims description 6
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 5
• 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 5
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 5
• 241001465754 Metazoa Species 0.000 claims description 5
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
• 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 5
• 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 5
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 4
• PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 claims description 4
• GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims description 4
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 4
• 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 4
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
• 125000004414 alkyl thio group Chemical group 0.000 claims description 4
• 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
• 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 4
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 4
• 125000002971 oxazolyl group Chemical group 0.000 claims description 4
• 125000003884 phenylalkyl group Chemical group 0.000 claims description 4
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 4
• SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 4
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 4
• 229940124597 therapeutic agent Drugs 0.000 claims description 4
• 230000001225 therapeutic effect Effects 0.000 claims description 4
• 125000004306 triazinyl group Chemical group 0.000 claims description 4
• 125000006526 (C1-C2) alkyl group Chemical group 0.000 claims description 3
• 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims description 3
• 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 3
• 241000124008 Mammalia Species 0.000 claims description 3
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 3
• 229920000180 alkyd Polymers 0.000 claims description 3
• 125000004429 atom Chemical group 0.000 claims description 3
• 125000004852 dihydrofuranyl group Chemical group O1C(CC=C1)* 0.000 claims description 3
• 125000005056 dihydrothiazolyl group Chemical group S1C(NC=C1)* 0.000 claims description 3
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 3
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 3
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 3
• QJZUKDFHGGYHMC-UHFFFAOYSA-N pyridine-3-carbaldehyde Chemical compound O=CC1=CC=CN=C1 QJZUKDFHGGYHMC-UHFFFAOYSA-N 0.000 claims description 3
• 125000001422 pyrrolinyl group Chemical group 0.000 claims description 3
• 125000006648 (C1-C8) haloalkyl group Chemical group 0.000 claims description 2
• 125000006593 (C2-C3) alkynyl group Chemical group 0.000 claims description 2
• 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 2
• 239000002256 antimetabolite Substances 0.000 claims description 2
• 230000003115 biocidal effect Effects 0.000 claims description 2
• 230000004663 cell proliferation Effects 0.000 claims description 2
• 125000004966 cyanoalkyl group Chemical group 0.000 claims description 2
• 125000005050 dihydrooxazolyl group Chemical group O1C(NC=C1)* 0.000 claims description 2
• 125000005057 dihydrothienyl group Chemical group S1C(CC=C1)* 0.000 claims description 2
• 239000003937 drug carrier Substances 0.000 claims description 2
• 125000004447 heteroarylalkenyl group Chemical group 0.000 claims description 2
• 229940125697 hormonal agent Drugs 0.000 claims description 2
• MWQREZAZLQIKHP-UHFFFAOYSA-N n-[3-[2-(dimethylamino)ethoxy]phenyl]-2-(1h-indazol-6-ylamino)pyridine-3-carboxamide Chemical compound CN(C)CCOC1=CC=CC(NC(=O)C=2C(=NC=CC=2)NC=2C=C3NN=CC3=CC=2)=C1 MWQREZAZLQIKHP-UHFFFAOYSA-N 0.000 claims description 2
• 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 2
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 2
• 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 2
• 235000014101 wine Nutrition 0.000 claims description 2
• 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 47
• 125000005246 nonafluorobutyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 claims 7
• 125000001786 isothiazolyl group Chemical group 0.000 claims 5
• 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims 4
• 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 claims 4
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims 4
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 4
• 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims 3
• 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 3
• 239000001273 butane Substances 0.000 claims 3
• IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims 3
• OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims 3
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 2
• 125000006592 (C2-C3) alkenyl group Chemical group 0.000 claims 2
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 2
• SXLRBECNMWOJCL-UHFFFAOYSA-N 2-(1h-indazol-6-ylamino)-n-[4-(1,1,2,2,2-pentafluoroethyl)-3-(pyrrolidin-2-ylmethoxy)phenyl]pyridine-3-carboxamide Chemical compound FC(F)(F)C(F)(F)C1=CC=C(NC(=O)C=2C(=NC=CC=2)NC=2C=C3NN=CC3=CC=2)C=C1OCC1CCCN1 SXLRBECNMWOJCL-UHFFFAOYSA-N 0.000 claims 2
• 241000009298 Trigla lyra Species 0.000 claims 2
• 150000001335 aliphatic alkanes Chemical class 0.000 claims 2
• 125000005466 alkylenyl group Chemical group 0.000 claims 2
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 2
• 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 1
• 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 1
• 125000005943 1,2,3,6-tetrahydropyridyl group Chemical group 0.000 claims 1
• 125000004521 1,3,4-thiadiazol-2-yl group Chemical group S1C(=NN=C1)* 0.000 claims 1
• QNJQVMKYMGRZHX-UHFFFAOYSA-N 2-(1h-indazol-6-ylamino)-n-(2,2,4-trimethyl-3h-1,4-benzoxazin-6-yl)pyridine-3-carboxamide Chemical compound C1=C2C=NNC2=CC(NC2=NC=CC=C2C(=O)NC2=CC=C3OC(C)(C)CN(C3=C2)C)=C1 QNJQVMKYMGRZHX-UHFFFAOYSA-N 0.000 claims 1
• XPVGZLJBEAYIHA-UHFFFAOYSA-N 2-(1h-indazol-6-ylamino)-n-[1-(2-morpholin-4-ylethyl)indol-6-yl]pyridine-3-carboxamide Chemical compound C=1C=CN=C(NC=2C=C3NN=CC3=CC=2)C=1C(=O)NC(C=C12)=CC=C1C=CN2CCN1CCOCC1 XPVGZLJBEAYIHA-UHFFFAOYSA-N 0.000 claims 1
• DEHGFLXRRPMVPC-UHFFFAOYSA-N 2-(1h-indazol-6-ylamino)-n-[3-(1-methylpiperidin-4-yl)-5-(trifluoromethyl)phenyl]pyridine-3-carboxamide Chemical compound C1CN(C)CCC1C1=CC(NC(=O)C=2C(=NC=CC=2)NC=2C=C3NN=CC3=CC=2)=CC(C(F)(F)F)=C1 DEHGFLXRRPMVPC-UHFFFAOYSA-N 0.000 claims 1
• AGGXMYIKPXOFLY-UHFFFAOYSA-N 2-(1h-indazol-6-ylamino)-n-[3-(4-methylpiperazin-1-yl)phenyl]pyridine-3-carboxamide Chemical compound C1CN(C)CCN1C1=CC=CC(NC(=O)C=2C(=NC=CC=2)NC=2C=C3NN=CC3=CC=2)=C1 AGGXMYIKPXOFLY-UHFFFAOYSA-N 0.000 claims 1
• ATYYPYPKVOJYLY-UHFFFAOYSA-N 2-(1h-indazol-6-ylamino)-n-[3-(pyrrolidin-2-ylmethoxy)-4-(trifluoromethyl)phenyl]pyridine-3-carboxamide Chemical compound FC(F)(F)C1=CC=C(NC(=O)C=2C(=NC=CC=2)NC=2C=C3NN=CC3=CC=2)C=C1OCC1CCCN1 ATYYPYPKVOJYLY-UHFFFAOYSA-N 0.000 claims 1
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• PMDUOJNIODWGHY-UHFFFAOYSA-N 2-(1h-indazol-6-ylamino)-n-[3-[3-(4-methylpiperazin-1-yl)-3-oxopropyl]phenyl]pyridine-3-carboxamide Chemical compound C1CN(C)CCN1C(=O)CCC1=CC=CC(NC(=O)C=2C(=NC=CC=2)NC=2C=C3NN=CC3=CC=2)=C1 PMDUOJNIODWGHY-UHFFFAOYSA-N 0.000 claims 1
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