EA020731B1 - Аминоазагетероциклические карбоксамиды - Google Patents

Info

Publication number

EA020731B1

EA020731B1 EA201101182A EA201101182A EA020731B1 EA 020731 B1 EA020731 B1 EA 020731B1 EA 201101182 A EA201101182 A EA 201101182A EA 201101182 A EA201101182 A EA 201101182A EA 020731 B1 EA020731 B1 EA 020731B1

Authority

EA

Eurasian Patent Office

Prior art keywords

quinazoline

amide

carboxylic acid

phenyl

ethylamino

Prior art date

2009-02-11

Links

• Espacenet
• Global Dossier
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• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 title claims abstract description 99
• 150000003857 carboxamides Chemical class 0.000 title description 7
• -1 carboxamide compounds Chemical class 0.000 claims abstract description 527
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 24
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 22
• 201000010099 disease Diseases 0.000 claims abstract description 19
• 201000011510 cancer Diseases 0.000 claims abstract description 17
• 230000003463 hyperproliferative effect Effects 0.000 claims abstract description 8
• 150000001408 amides Chemical class 0.000 claims description 459
• 150000001875 compounds Chemical class 0.000 claims description 407
• 239000002253 acid Substances 0.000 claims description 337
• 238000000034 method Methods 0.000 claims description 273
• 238000002360 preparation method Methods 0.000 claims description 122
• ASFAFOSQXBRFMV-LJQANCHMSA-N 3-n-(2-benzyl-1,3-dihydroxypropan-2-yl)-1-n-[(1r)-1-(4-fluorophenyl)ethyl]-5-[methyl(methylsulfonyl)amino]benzene-1,3-dicarboxamide Chemical compound N([C@H](C)C=1C=CC(F)=CC=1)C(=O)C(C=1)=CC(N(C)S(C)(=O)=O)=CC=1C(=O)NC(CO)(CO)CC1=CC=CC=C1 ASFAFOSQXBRFMV-LJQANCHMSA-N 0.000 claims description 119
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 97
• 238000006243 chemical reaction Methods 0.000 claims description 77
• 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 63
• 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 51
• UPGZAERNNNZSPM-UHFFFAOYSA-N quinazoline-8-carboxylic acid Chemical compound N1=CN=C2C(C(=O)O)=CC=CC2=C1 UPGZAERNNNZSPM-UHFFFAOYSA-N 0.000 claims description 51
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 47
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 46
• 150000003839 salts Chemical class 0.000 claims description 44
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 36
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 36
• GYBHRTQLUQOYID-UHFFFAOYSA-N quinazoline-8-carboxamide Chemical compound N1=CN=C2C(C(=O)N)=CC=CC2=C1 GYBHRTQLUQOYID-UHFFFAOYSA-N 0.000 claims description 28
• 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 25
• 229910052757 nitrogen Inorganic materials 0.000 claims description 17
• 229920006395 saturated elastomer Polymers 0.000 claims description 15
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 14
• 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 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
• 239000008194 pharmaceutical composition Substances 0.000 claims description 11
• 125000004429 atom Chemical group 0.000 claims description 10
• 150000002148 esters Chemical class 0.000 claims description 10
• DXASQZJWWGZNSF-UHFFFAOYSA-N n,n-dimethylmethanamine;sulfur trioxide Chemical group CN(C)C.O=S(=O)=O DXASQZJWWGZNSF-UHFFFAOYSA-N 0.000 claims description 10
• 239000003814 drug Substances 0.000 claims description 9
• 239000002246 antineoplastic agent Substances 0.000 claims description 8
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 8
• 125000004432 carbon atom Chemical group C* 0.000 claims description 7
• 229940079593 drug Drugs 0.000 claims description 7
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 6
• 239000003937 drug carrier Substances 0.000 claims description 6
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 6
• 229940124597 therapeutic agent Drugs 0.000 claims description 6
• 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 5
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 5
• 239000004480 active ingredient Substances 0.000 claims description 5
• 125000000217 alkyl group Chemical group 0.000 claims description 5
• 125000004076 pyridyl group Chemical group 0.000 claims description 5
• 206010061218 Inflammation Diseases 0.000 claims description 4
• 230000033115 angiogenesis Effects 0.000 claims description 4
• 229910052794 bromium Inorganic materials 0.000 claims description 4
• 230000004054 inflammatory process Effects 0.000 claims description 4
• UFEJKYYYVXYMMS-UHFFFAOYSA-N methylcarbamic acid Chemical compound CNC(O)=O UFEJKYYYVXYMMS-UHFFFAOYSA-N 0.000 claims description 4
• 125000003386 piperidinyl group Chemical group 0.000 claims description 4
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 4
• 125000000335 thiazolyl group Chemical group 0.000 claims description 4
• UALHJBCHHRMERK-UHFFFAOYSA-N 4-[[2-amino-1-(3,4-dichlorophenyl)ethyl]amino]quinazoline-8-carboxamide Chemical compound N=1C=NC2=C(C(N)=O)C=CC=C2C=1NC(CN)C1=CC=C(Cl)C(Cl)=C1 UALHJBCHHRMERK-UHFFFAOYSA-N 0.000 claims description 3
• 239000013256 coordination polymer Substances 0.000 claims description 3
• 206010012601 diabetes mellitus Diseases 0.000 claims description 3
• 125000000623 heterocyclic group Chemical group 0.000 claims description 3
• 229910052760 oxygen Inorganic materials 0.000 claims description 3
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
• 210000002307 prostate Anatomy 0.000 claims description 3
• 125000001424 substituent group Chemical group 0.000 claims description 3
• 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 2
• CKSGWNWLYXUENQ-UHFFFAOYSA-N 4-[(3,4-dimethylphenyl)methylamino]quinazoline-8-carboxamide Chemical class C1=C(C)C(C)=CC=C1CNC1=NC=NC2=C(C(N)=O)C=CC=C12 CKSGWNWLYXUENQ-UHFFFAOYSA-N 0.000 claims description 2
• KTVULQZLKLBGAM-UHFFFAOYSA-N 4-[1-[3-(1,3-benzodioxole-5-carbonylamino)phenyl]ethylamino]quinazoline-8-carboxylic acid Chemical compound O1COC2=C1C=CC(=C2)C(=O)NC=2C=C(C=CC2)C(C)NC2=NC=NC1=C(C=CC=C21)C(=O)O KTVULQZLKLBGAM-UHFFFAOYSA-N 0.000 claims description 2
• PHMDYYDCTPWPEK-UHFFFAOYSA-N 4-[1-[3-[(3-fluoro-4-methylbenzoyl)amino]phenyl]ethylamino]quinazoline-8-carboxylic acid Chemical compound FC=1C=C(C(=O)NC=2C=C(C=CC2)C(C)NC2=NC=NC3=C(C=CC=C23)C(=O)O)C=CC1C PHMDYYDCTPWPEK-UHFFFAOYSA-N 0.000 claims description 2
• BYUUFRNHCFTPTI-UHFFFAOYSA-N 4-[[1-(3,4-dichlorophenyl)-2-(methylamino)ethyl]amino]quinazoline-8-carboxamide Chemical compound N=1C=NC2=C(C(N)=O)C=CC=C2C=1NC(CNC)C1=CC=C(Cl)C(Cl)=C1 BYUUFRNHCFTPTI-UHFFFAOYSA-N 0.000 claims description 2
• HZCSYARAUKXOFF-UHFFFAOYSA-N 4-[[1-(3-benzamidophenyl)-2-(methylamino)ethyl]amino]quinazoline-8-carboxamide Chemical compound N=1C=NC2=C(C(N)=O)C=CC=C2C=1NC(CNC)C(C=1)=CC=CC=1NC(=O)C1=CC=CC=C1 HZCSYARAUKXOFF-UHFFFAOYSA-N 0.000 claims description 2
• MVJNPYHZOCRHCN-UHFFFAOYSA-N 4-[[1-(3-chlorophenyl)-2-(methylamino)ethyl]amino]-6-phenylmethoxyquinazoline-8-carboxylic acid Chemical compound CNCC(Nc1ncnc2c(cc(OCc3ccccc3)cc12)C(O)=O)c1cccc(Cl)c1 MVJNPYHZOCRHCN-UHFFFAOYSA-N 0.000 claims description 2
• ICFSTMCCCHREQT-UHFFFAOYSA-N 4-[[1-[3-[(2,4-difluorobenzoyl)amino]phenyl]-3-methoxypropyl]amino]quinazoline-8-carboxylic acid Chemical compound COCCC(C1=CC(=CC=C1)NC(C1=C(C=C(C=C1)F)F)=O)NC1=NC=NC2=C(C=CC=C12)C(=O)O ICFSTMCCCHREQT-UHFFFAOYSA-N 0.000 claims description 2
• FFJNCCISXWZBSC-UHFFFAOYSA-N 4-[[1-[3-[(2,6-difluorobenzoyl)amino]phenyl]-3-methoxypropyl]amino]quinazoline-8-carboxamide Chemical compound N=1C=NC2=C(C(N)=O)C=CC=C2C=1NC(CCOC)C(C=1)=CC=CC=1NC(=O)C1=C(F)C=CC=C1F FFJNCCISXWZBSC-UHFFFAOYSA-N 0.000 claims description 2
• FIZSPRJMYGKSMB-UHFFFAOYSA-N 4-[[1-[3-[(3,4-difluorobenzoyl)amino]phenyl]-2-(methylamino)ethyl]amino]quinazoline-8-carboxamide Chemical compound N=1C=NC2=C(C(N)=O)C=CC=C2C=1NC(CNC)C(C=1)=CC=CC=1NC(=O)C1=CC=C(F)C(F)=C1 FIZSPRJMYGKSMB-UHFFFAOYSA-N 0.000 claims description 2
• UUQUQPUHXKTHDD-UHFFFAOYSA-N 4-[[1-[3-[(3-fluoro-4-methoxybenzoyl)amino]phenyl]-2-(methylamino)ethyl]amino]quinazoline-8-carboxamide Chemical compound N=1C=NC2=C(C(N)=O)C=CC=C2C=1NC(CNC)C(C=1)=CC=CC=1NC(=O)C1=CC=C(OC)C(F)=C1 UUQUQPUHXKTHDD-UHFFFAOYSA-N 0.000 claims description 2
• LYOMZOFITVVBNX-UHFFFAOYSA-N 4-[[2-(dimethylamino)-1-[3-[(3-fluoro-4-methoxybenzoyl)amino]phenyl]ethyl]amino]quinazoline-8-carboxamide Chemical compound C1=C(F)C(OC)=CC=C1C(=O)NC1=CC=CC(C(CN(C)C)NC=2C3=CC=CC(=C3N=CN=2)C(N)=O)=C1 LYOMZOFITVVBNX-UHFFFAOYSA-N 0.000 claims description 2
• FPKMBCYLLRYVBK-UHFFFAOYSA-N 4-[[2-(methylamino)-1-[3-[[4-(trifluoromethyl)benzoyl]amino]phenyl]ethyl]amino]quinazoline-8-carboxylic acid Chemical compound N=1C=NC2=C(C(O)=O)C=CC=C2C=1NC(CNC)C(C=1)=CC=CC=1NC(=O)C1=CC=C(C(F)(F)F)C=C1 FPKMBCYLLRYVBK-UHFFFAOYSA-N 0.000 claims description 2
• KFUGVCOVSKGHMS-UHFFFAOYSA-N 4-[[2-(methylamino)-1-phenylethyl]amino]quinazoline-8-carboxamide Chemical class N=1C=NC2=C(C(N)=O)C=CC=C2C=1NC(CNC)C1=CC=CC=C1 KFUGVCOVSKGHMS-UHFFFAOYSA-N 0.000 claims description 2
• YCUXZFDOLJQXOU-UHFFFAOYSA-N 4-[[2-amino-1-(3-methoxyphenyl)ethyl]amino]quinazoline-8-carboxamide Chemical compound COC1=CC=CC(C(CN)NC=2C3=CC=CC(=C3N=CN=2)C(N)=O)=C1 YCUXZFDOLJQXOU-UHFFFAOYSA-N 0.000 claims description 2
• BXSXPCFESWIUHR-UHFFFAOYSA-N 4-[[4-chloro-3-(trifluoromethyl)phenyl]methylamino]quinazoline-8-carboxamide Chemical compound N1=CN=C2C(C(=O)N)=CC=CC2=C1NCC1=CC=C(Cl)C(C(F)(F)F)=C1 BXSXPCFESWIUHR-UHFFFAOYSA-N 0.000 claims description 2
• KVFYDXGGQHSXLI-UHFFFAOYSA-N BrC1=CC=C(C(=O)NC=2C=C(C=CC2)C(CNC)NC2=NC=NC3=C(C=CC=C23)C(=O)O)C=C1 Chemical compound BrC1=CC=C(C(=O)NC=2C=C(C=CC2)C(CNC)NC2=NC=NC3=C(C=CC=C23)C(=O)O)C=C1 KVFYDXGGQHSXLI-UHFFFAOYSA-N 0.000 claims description 2
• ASPLSKGEAUOQQA-UHFFFAOYSA-N CN(CCC(C1=CC(=CC=C1)NC(C1=CC=C(C=C1)Br)=O)NC1=NC=NC2=C(C=CC=C12)C(=O)O)C Chemical compound CN(CCC(C1=CC(=CC=C1)NC(C1=CC=C(C=C1)Br)=O)NC1=NC=NC2=C(C=CC=C12)C(=O)O)C ASPLSKGEAUOQQA-UHFFFAOYSA-N 0.000 claims description 2
• JRZOIXBASRXFMU-UHFFFAOYSA-N COC1=CC=C(C(=O)NC=2C=C(C=CC2)C(CNC)NC2=NC=NC3=C(C=CC=C23)C(=O)O)C=C1 Chemical compound COC1=CC=C(C(=O)NC=2C=C(C=CC2)C(CNC)NC2=NC=NC3=C(C=CC=C23)C(=O)O)C=C1 JRZOIXBASRXFMU-UHFFFAOYSA-N 0.000 claims description 2
• 201000004624 Dermatitis Diseases 0.000 claims description 2
• 206010012689 Diabetic retinopathy Diseases 0.000 claims description 2
• 208000032612 Glial tumor Diseases 0.000 claims description 2
• 206010018338 Glioma Diseases 0.000 claims description 2
• 208000007766 Kaposi sarcoma Diseases 0.000 claims description 2
• 201000004681 Psoriasis Diseases 0.000 claims description 2
• 206010038933 Retinopathy of prematurity Diseases 0.000 claims description 2
• 206010039710 Scleroderma Diseases 0.000 claims description 2
• 206010064930 age-related macular degeneration Diseases 0.000 claims description 2
• 125000002947 alkylene group Chemical group 0.000 claims description 2
• 208000010668 atopic eczema Diseases 0.000 claims description 2
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 2
• 239000011737 fluorine Substances 0.000 claims description 2
• 229910052731 fluorine Inorganic materials 0.000 claims description 2
• 229910052740 iodine Inorganic materials 0.000 claims description 2
• 208000002780 macular degeneration Diseases 0.000 claims description 2
• 201000001441 melanoma Diseases 0.000 claims description 2
• 125000002950 monocyclic group Chemical group 0.000 claims description 2
• 125000006413 ring segment Chemical group 0.000 claims description 2
• 208000017520 skin disease Diseases 0.000 claims description 2
• 230000005747 tumor angiogenesis Effects 0.000 claims description 2
• 230000004862 vasculogenesis Effects 0.000 claims description 2
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
• SGZFLJKVODZGJM-UHFFFAOYSA-N 4-[[2-amino-1-(3,4-dimethoxyphenyl)ethyl]amino]quinazoline-8-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1C(CN)NC1=NC=NC2=C(C(N)=O)C=CC=C12 SGZFLJKVODZGJM-UHFFFAOYSA-N 0.000 claims 2
• SMNAZESEEXRTTQ-UHFFFAOYSA-N NCC(C1=CC=C(C=C1)OC)NC1=NC=NC2=C(C=CC=C12)C(=O)O Chemical compound NCC(C1=CC=C(C=C1)OC)NC1=NC=NC2=C(C=CC=C12)C(=O)O SMNAZESEEXRTTQ-UHFFFAOYSA-N 0.000 claims 2
• GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 claims 2
• 125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 claims 1
• QBWMPYZCKOEWSU-UHFFFAOYSA-N 4-[1-[3-[(4-bromobenzoyl)amino]phenyl]ethylamino]quinazoline-8-carboxamide Chemical compound N=1C=NC2=C(C(N)=O)C=CC=C2C=1NC(C)C(C=1)=CC=CC=1NC(=O)C1=CC=C(Br)C=C1 QBWMPYZCKOEWSU-UHFFFAOYSA-N 0.000 claims 1
• AGDQZNITYJKXQO-UHFFFAOYSA-N 4-[[1-(3,4-dichlorophenyl)-2-(dimethylamino)ethyl]amino]quinazoline-8-carboxamide Chemical compound N=1C=NC2=C(C(N)=O)C=CC=C2C=1NC(CN(C)C)C1=CC=C(Cl)C(Cl)=C1 AGDQZNITYJKXQO-UHFFFAOYSA-N 0.000 claims 1
• QZMSENZZQWAYFQ-UHFFFAOYSA-N 4-[[1-(3-bromophenyl)-2-(dimethylamino)ethyl]amino]quinazoline-8-carboxamide Chemical compound N=1C=NC2=C(C(N)=O)C=CC=C2C=1NC(CN(C)C)C1=CC=CC(Br)=C1 QZMSENZZQWAYFQ-UHFFFAOYSA-N 0.000 claims 1
• ODIBHBBABRKJIO-UHFFFAOYSA-N 4-[[1-(3-chlorophenyl)-2-(dimethylamino)ethyl]amino]quinazoline-8-carboxamide Chemical compound N=1C=NC2=C(C(N)=O)C=CC=C2C=1NC(CN(C)C)C1=CC=CC(Cl)=C1 ODIBHBBABRKJIO-UHFFFAOYSA-N 0.000 claims 1
• LAJBTQZYEORIHT-UHFFFAOYSA-N 4-[[1-(3-chlorophenyl)-2-(methylamino)ethyl]amino]quinazoline-8-carboxylic acid Chemical compound ClC=1C=C(C=CC1)C(CNC)NC1=NC=NC2=C(C=CC=C12)C(=O)O LAJBTQZYEORIHT-UHFFFAOYSA-N 0.000 claims 1
• RBMOLIOJAWRTIV-UHFFFAOYSA-N 4-[[1-(3-fluorophenyl)-2-(methylamino)ethyl]amino]quinazoline-8-carboxamide Chemical class N=1C=NC2=C(C(N)=O)C=CC=C2C=1NC(CNC)C1=CC=CC(F)=C1 RBMOLIOJAWRTIV-UHFFFAOYSA-N 0.000 claims 1
• CJAKBHSFDAWLEM-UHFFFAOYSA-N 4-[[1-(4-chlorophenyl)-2-(dimethylamino)ethyl]amino]-6-methoxyquinazoline-8-carboxamide Chemical compound C12=CC(OC)=CC(C(N)=O)=C2N=CN=C1NC(CN(C)C)C1=CC=C(Cl)C=C1 CJAKBHSFDAWLEM-UHFFFAOYSA-N 0.000 claims 1
• ZJKRQNYRWHKMJV-UHFFFAOYSA-N 4-[[1-(4-methoxyphenyl)-2-(methylamino)ethyl]amino]quinazoline-8-carboxamide Chemical compound N=1C=NC2=C(C(N)=O)C=CC=C2C=1NC(CNC)C1=CC=C(OC)C=C1 ZJKRQNYRWHKMJV-UHFFFAOYSA-N 0.000 claims 1
• MFRRIEBIBJQMAF-UHFFFAOYSA-N 4-[[1-[3-[(2,4-difluorobenzoyl)amino]phenyl]-3-(dimethylamino)propyl]amino]quinazoline-8-carboxamide Chemical compound N=1C=NC2=C(C(N)=O)C=CC=C2C=1NC(CCN(C)C)C(C=1)=CC=CC=1NC(=O)C1=CC=C(F)C=C1F MFRRIEBIBJQMAF-UHFFFAOYSA-N 0.000 claims 1
• PWHBJAGRMMCMCJ-UHFFFAOYSA-N 4-[[1-[3-[(4-bromobenzoyl)amino]phenyl]-2-(dimethylamino)ethyl]amino]quinazoline-8-carboxylic acid Chemical compound CN(C)CC(Nc1ncnc2c(cccc12)C(O)=O)c1cccc(NC(=O)c2ccc(Br)cc2)c1 PWHBJAGRMMCMCJ-UHFFFAOYSA-N 0.000 claims 1
• GWUYLDMVDQHMJN-UHFFFAOYSA-N 4-[[2-(dimethylamino)-1-(3-fluorophenyl)ethyl]amino]-6-ethoxyquinazoline-8-carboxamide Chemical compound C12=CC(OCC)=CC(C(N)=O)=C2N=CN=C1NC(CN(C)C)C1=CC=CC(F)=C1 GWUYLDMVDQHMJN-UHFFFAOYSA-N 0.000 claims 1
• ALLGNFRRMBCRHD-UHFFFAOYSA-N 4-[[2-(dimethylamino)-1-(3-methoxyphenyl)ethyl]amino]quinazoline-8-carboxamide Chemical compound COC1=CC=CC(C(CN(C)C)NC=2C3=CC=CC(=C3N=CN=2)C(N)=O)=C1 ALLGNFRRMBCRHD-UHFFFAOYSA-N 0.000 claims 1
• DCRRXSUQGXVDLQ-UHFFFAOYSA-N 4-[[2-(dimethylamino)-1-[3-[(5-pyrrolidin-1-ylpyridine-3-carbonyl)amino]phenyl]ethyl]amino]quinazoline-8-carboxamide Chemical compound N=1C=NC2=C(C(N)=O)C=CC=C2C=1NC(CN(C)C)C(C=1)=CC=CC=1NC(=O)C(C=1)=CN=CC=1N1CCCC1 DCRRXSUQGXVDLQ-UHFFFAOYSA-N 0.000 claims 1
• RXAZPQCDGXHCAO-UHFFFAOYSA-N 4-[[2-(dimethylamino)-1-[3-[[4-(trifluoromethyl)benzoyl]amino]phenyl]ethyl]amino]quinazoline-8-carboxamide Chemical compound N=1C=NC2=C(C(N)=O)C=CC=C2C=1NC(CN(C)C)C(C=1)=CC=CC=1NC(=O)C1=CC=C(C(F)(F)F)C=C1 RXAZPQCDGXHCAO-UHFFFAOYSA-N 0.000 claims 1
• ZJDZJPZEQDNRHD-UHFFFAOYSA-N 4-[[2-(dimethylamino)-1-[4-(trifluoromethyl)phenyl]ethyl]amino]quinazoline-8-carboxamide Chemical compound N=1C=NC2=C(C(N)=O)C=CC=C2C=1NC(CN(C)C)C1=CC=C(C(F)(F)F)C=C1 ZJDZJPZEQDNRHD-UHFFFAOYSA-N 0.000 claims 1
• ZHHSRQFICBOYCE-UHFFFAOYSA-N 4-[[2-(methylamino)-1-[3-[[4-(trifluoromethoxy)benzoyl]amino]phenyl]ethyl]amino]quinazoline-8-carboxamide Chemical compound N=1C=NC2=C(C(N)=O)C=CC=C2C=1NC(CNC)C(C=1)=CC=CC=1NC(=O)C1=CC=C(OC(F)(F)F)C=C1 ZHHSRQFICBOYCE-UHFFFAOYSA-N 0.000 claims 1
• CHCRIZDVAZHKPK-UHFFFAOYSA-N 4-[[2-amino-1-(4-methylphenyl)ethyl]amino]quinazoline-8-carboxylic acid Chemical compound NCC(C1=CC=C(C=C1)C)NC1=NC=NC2=C(C=CC=C12)C(=O)O CHCRIZDVAZHKPK-UHFFFAOYSA-N 0.000 claims 1
• FTLGJGCPUAMLIH-UHFFFAOYSA-N 4-[[3-[[2-[2-hydroxyethyl(methyl)amino]pyridine-4-carbonyl]amino]phenyl]methylamino]quinazoline-8-carboxamide Chemical compound C1=NC(N(CCO)C)=CC(C(=O)NC=2C=C(CNC=3C4=CC=CC(=C4N=CN=3)C(N)=O)C=CC=2)=C1 FTLGJGCPUAMLIH-UHFFFAOYSA-N 0.000 claims 1
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