MX2007006230A - Quinolinas y analogos de quinazolinas y su uso como medicamentos para tratar cancer. - Google Patents

Info

Publication number

MX2007006230A

MX2007006230A MX2007006230A MX2007006230A MX2007006230A MX 2007006230 A MX2007006230 A MX 2007006230A MX 2007006230 A MX2007006230 A MX 2007006230A MX 2007006230 A MX2007006230 A MX 2007006230A MX 2007006230 A MX2007006230 A MX 2007006230A

Authority

MX

Mexico

Prior art keywords

phenyl

oxy

fluoro

methoxy

methyl

Prior art date

2004-11-30

Links

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• Global Dossier
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• 206010028980 Neoplasm Diseases 0.000 title claims abstract description 53
• 201000011510 cancer Diseases 0.000 title claims abstract description 17
• 239000003814 drug Substances 0.000 title claims description 17
• 229940111121 antirheumatic drug quinolines Drugs 0.000 title description 4
• 125000002294 quinazolinyl group Chemical class N1=C(N=CC2=CC=CC=C12)* 0.000 title 1
• 150000003248 quinolines Chemical class 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 344
• 101000898034 Homo sapiens Hepatocyte growth factor Proteins 0.000 claims abstract description 48
• 102100021866 Hepatocyte growth factor Human genes 0.000 claims abstract description 47
• 125000003118 aryl group Chemical group 0.000 claims abstract description 41
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 41
• 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 14
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 11
• 230000001404 mediated effect Effects 0.000 claims abstract description 8
• -1 piperazin-4-yl Chemical group 0.000 claims description 478
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 117
• 238000002360 preparation method Methods 0.000 claims description 72
• 125000000623 heterocyclic group Chemical group 0.000 claims description 62
• 238000011282 treatment Methods 0.000 claims description 60
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 59
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 59
• 125000000217 alkyl group Chemical group 0.000 claims description 57
• YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 55
• 150000003839 salts Chemical class 0.000 claims description 49
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 34
• 125000005113 hydroxyalkoxy group Chemical group 0.000 claims description 32
• 239000003795 chemical substances by application Substances 0.000 claims description 30
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 29
• 230000033115 angiogenesis Effects 0.000 claims description 26
• 125000001153 fluoro group Chemical group F* 0.000 claims description 26
• 125000003342 alkenyl group Chemical group 0.000 claims description 25
• 125000001188 haloalkyl group Chemical group 0.000 claims description 25
• 229910052799 carbon Inorganic materials 0.000 claims description 24
• 125000005843 halogen group Chemical group 0.000 claims description 24
• 125000000304 alkynyl group Chemical group 0.000 claims description 23
• 125000003282 alkyl amino group Chemical group 0.000 claims description 22
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 22
• 229910052739 hydrogen Inorganic materials 0.000 claims description 21
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 19
• 125000003545 alkoxy group Chemical group 0.000 claims description 18
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 18
• 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 17
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 15
• 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 15
• 125000001786 isothiazolyl group Chemical group 0.000 claims description 15
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 14
• 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 14
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 13
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 13
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 13
• 125000001544 thienyl group Chemical group 0.000 claims description 13
• 125000002541 furyl group Chemical group 0.000 claims description 12
• 125000002883 imidazolyl group Chemical group 0.000 claims description 12
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 12
• 125000002971 oxazolyl group Chemical group 0.000 claims description 12
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 12
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 11
• 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 11
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 11
• 125000004076 pyridyl group Chemical group 0.000 claims description 11
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 11
• 125000000335 thiazolyl group Chemical group 0.000 claims description 11
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 10
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 10
• 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 10
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 10
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 10
• 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 9
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 9
• 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 9
• YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 9
• DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims description 9
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 9
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 9
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 9
• HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 9
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])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
• CWDWFSXUQODZGW-UHFFFAOYSA-N 5-thiazolyl Chemical group [C]1=CN=CS1 CWDWFSXUQODZGW-UHFFFAOYSA-N 0.000 claims description 8
• 206010027476 Metastases Diseases 0.000 claims description 8
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 8
• 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 8
• 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 8
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
• 230000009401 metastasis Effects 0.000 claims description 8
• 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 8
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 8
• 230000009467 reduction Effects 0.000 claims description 8
• 125000001424 substituent group Chemical group 0.000 claims description 8
• 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 7
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 7
• 125000003386 piperidinyl group Chemical group 0.000 claims description 7
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 7
• FQGNDEQDYLPOOE-UHFFFAOYSA-N 1-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-4-(phenoxymethyl)pyrrolidin-2-one Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1N(C(C1)=O)CC1COC1=CC=CC=C1 FQGNDEQDYLPOOE-UHFFFAOYSA-N 0.000 claims description 6
• 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims description 6
• KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical group [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 claims description 6
• 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 6
• ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 6
• YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 6
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 6
• 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 6
• 125000004193 piperazinyl group Chemical group 0.000 claims description 6
• 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 6
• 125000005871 1,3-benzodioxolyl group Chemical group 0.000 claims description 5
• 125000004104 aryloxy group Chemical group 0.000 claims description 5
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 5
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 5
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 5
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
• 229910052727 yttrium Inorganic materials 0.000 claims description 5
• 239000002256 antimetabolite Substances 0.000 claims description 4
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 4
• 125000005191 hydroxyalkylamino group Chemical group 0.000 claims description 4
• 125000004499 isoxazol-5-yl group Chemical group O1N=CC=C1* 0.000 claims description 4
• DOANCNPFSRWFRV-UHFFFAOYSA-N n-[1-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-5-oxopyrrolidin-3-yl]benzamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1N(C(C1)=O)CC1NC(=O)C1=CC=CC=C1 DOANCNPFSRWFRV-UHFFFAOYSA-N 0.000 claims description 4
• 125000005412 pyrazyl group Chemical group 0.000 claims description 4
• 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims description 4
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
• DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical compound O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 claims description 3
• LNRVNLVNYOEOKV-UHFFFAOYSA-N 2-(2,2-dimethylpropylamino)-5-[3-fluoro-4-[6-methoxy-7-(3-morpholin-4-ylpropoxy)quinolin-4-yl]oxyphenyl]-3-methylpyrimidin-4-one Chemical compound C1=CN=C2C=C(OCCCN3CCOCC3)C(OC)=CC2=C1OC(C(=C1)F)=CC=C1C1=CN=C(NCC(C)(C)C)N(C)C1=O LNRVNLVNYOEOKV-UHFFFAOYSA-N 0.000 claims description 3
• ONSZEUCTVQJHOZ-UHFFFAOYSA-N 2-(4-fluoroanilino)-5-[3-fluoro-4-[6-methoxy-7-(3-morpholin-4-ylpropoxy)quinolin-4-yl]oxyphenyl]-3-methylpyrimidin-4-one Chemical compound C1=CN=C2C=C(OCCCN3CCOCC3)C(OC)=CC2=C1OC(C(=C1)F)=CC=C1C(C(N1C)=O)=CN=C1NC1=CC=C(F)C=C1 ONSZEUCTVQJHOZ-UHFFFAOYSA-N 0.000 claims description 3
• PCXQKKAKSPFWPY-UHFFFAOYSA-N 2-[4-(dimethylamino)anilino]-5-[3-fluoro-4-[6-methoxy-7-(3-morpholin-4-ylpropoxy)quinolin-4-yl]oxyphenyl]-3-methylpyrimidin-4-one Chemical compound C1=CN=C2C=C(OCCCN3CCOCC3)C(OC)=CC2=C1OC(C(=C1)F)=CC=C1C(C(N1C)=O)=CN=C1NC1=CC=C(N(C)C)C=C1 PCXQKKAKSPFWPY-UHFFFAOYSA-N 0.000 claims description 3
• XFEYXKJPGONJJO-UHFFFAOYSA-N 2-benzyl-5-[3-fluoro-4-[6-methoxy-7-[3-(4-methylpiperazin-1-yl)propoxy]quinolin-4-yl]oxyphenyl]-3-methylpyrimidin-4-one Chemical compound C1=CN=C2C=C(OCCCN3CCN(C)CC3)C(OC)=CC2=C1OC(C(=C1)F)=CC=C1C(C(N1C)=O)=CN=C1CC1=CC=CC=C1 XFEYXKJPGONJJO-UHFFFAOYSA-N 0.000 claims description 3
• IKPJWGNTDNCFPS-UHFFFAOYSA-N 2-benzyl-5-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-3-methylpyrimidin-4-one Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1C(C(N1C)=O)=CN=C1CC1=CC=CC=C1 IKPJWGNTDNCFPS-UHFFFAOYSA-N 0.000 claims description 3
• KJHKYWUGNVFQAU-UHFFFAOYSA-N 4-[4-[6-(2,3-dihydroindol-1-yl)pyridazin-3-yl]-2-fluorophenoxy]-6,7-dimethoxyquinoline Chemical class C1CC2=CC=CC=C2N1C(N=N1)=CC=C1C(C=C1F)=CC=C1OC1=C(C=C(C(OC)=C2)OC)C2=NC=C1 KJHKYWUGNVFQAU-UHFFFAOYSA-N 0.000 claims description 3
• DUTNABYDBFVZOA-UHFFFAOYSA-N 5-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-2-(4-fluoroanilino)-3-methylpyrimidin-4-one Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1C(C(N1C)=O)=CN=C1NC1=CC=C(F)C=C1 DUTNABYDBFVZOA-UHFFFAOYSA-N 0.000 claims description 3
• BKSWYOHROKZGQJ-UHFFFAOYSA-N 5-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-3-methyl-2-methylsulfanylpyrimidin-4-one Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1C1=CN=C(SC)N(C)C1=O BKSWYOHROKZGQJ-UHFFFAOYSA-N 0.000 claims description 3
• AWYLSMAUCAFISX-UHFFFAOYSA-N 6-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-n-(3-fluorophenyl)pyridazin-3-amine Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1C(N=N1)=CC=C1NC1=CC=CC(F)=C1 AWYLSMAUCAFISX-UHFFFAOYSA-N 0.000 claims description 3
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 3
• 229940100198 alkylating agent Drugs 0.000 claims description 3
• 239000002168 alkylating agent Substances 0.000 claims description 3
• 230000003115 biocidal effect Effects 0.000 claims description 3
• 229940125697 hormonal agent Drugs 0.000 claims description 3
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 3
• 239000008194 pharmaceutical composition Substances 0.000 claims description 3
• 125000005936 piperidyl group Chemical group 0.000 claims description 3
• 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 3
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
• 125000003944 tolyl group Chemical group 0.000 claims description 3
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 2
• VIESAWGOYVNHLV-UHFFFAOYSA-N 1,3-dihydropyrrol-2-one Chemical compound O=C1CC=CN1 VIESAWGOYVNHLV-UHFFFAOYSA-N 0.000 claims description 2
• 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
• UBDLWVOLOGMUTH-UHFFFAOYSA-N 2-(cyclopropylmethylamino)-5-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-3-methylpyrimidin-4-one Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1C(C(N1C)=O)=CN=C1NCC1CC1 UBDLWVOLOGMUTH-UHFFFAOYSA-N 0.000 claims description 2
• PKIZVMUVKINBQA-RUZDIDTESA-N 2-benzyl-5-[3-fluoro-4-[7-[(2r)-2-hydroxy-3-morpholin-4-ylpropoxy]-6-methoxyquinolin-4-yl]oxyphenyl]-3-methylpyrimidin-4-one Chemical compound C1=CN=C2C=C(OC[C@H](O)CN3CCOCC3)C(OC)=CC2=C1OC(C(=C1)F)=CC=C1C(C(N1C)=O)=CN=C1CC1=CC=CC=C1 PKIZVMUVKINBQA-RUZDIDTESA-N 0.000 claims description 2
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 2
• YVXPEAVBPWBAOO-UHFFFAOYSA-N 2-cyclopentyl-5-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-3-methylpyrimidin-4-one Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1C(C(N1C)=O)=CN=C1C1CCCC1 YVXPEAVBPWBAOO-UHFFFAOYSA-N 0.000 claims description 2
• 125000006304 2-iodophenyl group Chemical group [H]C1=C([H])C(I)=C(*)C([H])=C1[H] 0.000 claims description 2
• BFJLGZQECBDICL-UHFFFAOYSA-N 5-[3-fluoro-4-[6-methoxy-7-(3-morpholin-4-ylpropoxy)quinolin-4-yl]oxyphenyl]-2-[hydroxy(phenyl)methyl]-3-methylpyrimidin-4-one Chemical compound C1=CN=C2C=C(OCCCN3CCOCC3)C(OC)=CC2=C1OC(C(=C1)F)=CC=C1C(C(N1C)=O)=CN=C1C(O)C1=CC=CC=C1 BFJLGZQECBDICL-UHFFFAOYSA-N 0.000 claims description 2
• DRSPEQIWHFQYLU-UHFFFAOYSA-N 5-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-2-(3-fluoroanilino)-3-methylpyrimidin-4-one Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1C(C(N1C)=O)=CN=C1NC1=CC=CC(F)=C1 DRSPEQIWHFQYLU-UHFFFAOYSA-N 0.000 claims description 2
• UCWBIBYVEQMUJR-UHFFFAOYSA-N 5-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-3-methyl-2-pyrrolidin-1-ylpyrimidin-4-one Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1C(C(N1C)=O)=CN=C1N1CCCC1 UCWBIBYVEQMUJR-UHFFFAOYSA-N 0.000 claims description 2
• FVCWENINFRMZBW-UHFFFAOYSA-N 6,7-dimethoxy-4-(6-methyl-2-thiophen-3-ylpyridin-3-yl)oxyquinoline Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC1=CC=C(C)N=C1C=1C=CSC=1 FVCWENINFRMZBW-UHFFFAOYSA-N 0.000 claims description 2
• MBUBVYJEWQXONT-UHFFFAOYSA-N 6-[3-fluoro-4-[6-methoxy-7-(3-morpholin-4-ylpropoxy)quinolin-4-yl]oxyphenyl]-n-phenylpyridazin-3-amine Chemical compound C1=CN=C2C=C(OCCCN3CCOCC3)C(OC)=CC2=C1OC(C(=C1)F)=CC=C1C(N=N1)=CC=C1NC1=CC=CC=C1 MBUBVYJEWQXONT-UHFFFAOYSA-N 0.000 claims description 2
• LAMJVDBQSQOXNA-UHFFFAOYSA-N 6-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-n-(2,2,2-trifluoroethyl)pyridazin-3-amine Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1C1=CC=C(NCC(F)(F)F)N=N1 LAMJVDBQSQOXNA-UHFFFAOYSA-N 0.000 claims description 2
• XTGUDWBGLVVSHS-UHFFFAOYSA-N 6-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-n-(2,3-dimethylphenyl)pyridazin-3-amine Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1C(N=N1)=CC=C1NC1=CC=CC(C)=C1C XTGUDWBGLVVSHS-UHFFFAOYSA-N 0.000 claims description 2
• KISGDJNTHJAZCC-UHFFFAOYSA-N 6-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-n-(2-methoxyphenyl)pyridazin-3-amine Chemical compound COC1=CC=CC=C1NC1=CC=C(C=2C=C(F)C(OC=3C4=CC(OC)=C(OC)C=C4N=CC=3)=CC=2)N=N1 KISGDJNTHJAZCC-UHFFFAOYSA-N 0.000 claims description 2
• MOKHEEYKZMBRIA-UHFFFAOYSA-N 6-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-n-phenylpyridazin-3-amine Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1C(N=N1)=CC=C1NC1=CC=CC=C1 MOKHEEYKZMBRIA-UHFFFAOYSA-N 0.000 claims description 2
• CQKRIQRZTAMFET-UHFFFAOYSA-N FC=1C=C(C=CC=1OC1=CC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1)N1C(N(CC1=O)C(C)C1=CC=CC=C1)=O Chemical compound FC=1C=C(C=CC=1OC1=CC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1)N1C(N(CC1=O)C(C)C1=CC=CC=C1)=O CQKRIQRZTAMFET-UHFFFAOYSA-N 0.000 claims description 2
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
• 239000003937 drug carrier Substances 0.000 claims description 2
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
• 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 2
• 239000000677 immunologic agent Substances 0.000 claims description 2
• 229940124541 immunological agent Drugs 0.000 claims description 2
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