LV13024B - Tricyclic 2-pyridone compounds useful as hiv reverse transcriptase inhibitors - Google Patents

Info

Publication number

LV13024B

LV13024B LVP-03-16A LV030016A LV13024B LV 13024 B LV13024 B LV 13024B LV 030016 A LV030016 A LV 030016A LV 13024 B LV13024 B LV 13024B

Authority

LV

Latvia

Prior art keywords

naphthyridin

dihydrobenzo

group

substituted

trifluoromethyl

Prior art date

2000-07-20

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• 108010078851 HIV Reverse Transcriptase Proteins 0.000 title claims abstract description 22
• 239000003419 rna directed dna polymerase inhibitor Substances 0.000 title claims description 27
• UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical class OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 title abstract description 9
• 239000000203 mixture Substances 0.000 claims abstract description 88
• 150000003839 salts Chemical group 0.000 claims abstract description 44
• 239000003112 inhibitor Substances 0.000 claims abstract description 21
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 8
• 150000001875 compounds Chemical class 0.000 claims description 325
• -1 cyclic amine Chemical class 0.000 claims description 251
• 125000000217 alkyl group Chemical group 0.000 claims description 169
• 229910052801 chlorine Inorganic materials 0.000 claims description 112
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 111
• 229910052731 fluorine Inorganic materials 0.000 claims description 108
• 229910052739 hydrogen Inorganic materials 0.000 claims description 96
• 125000003545 alkoxy group Chemical group 0.000 claims description 90
• 229910052794 bromium Inorganic materials 0.000 claims description 86
• 229910052757 nitrogen Inorganic materials 0.000 claims description 82
• 229910052740 iodine Inorganic materials 0.000 claims description 77
• 229910052799 carbon Inorganic materials 0.000 claims description 64
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 59
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 58
• 125000005842 heteroatom Chemical group 0.000 claims description 58
• 229910052717 sulfur Inorganic materials 0.000 claims description 56
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 43
• 125000000623 heterocyclic group Chemical group 0.000 claims description 42
• 125000000304 alkynyl group Chemical group 0.000 claims description 41
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 39
• QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims description 37
• 125000003342 alkenyl group Chemical group 0.000 claims description 36
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 34
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 31
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 29
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 29
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 26
• 208000031886 HIV Infections Diseases 0.000 claims description 25
• 208000037357 HIV infectious disease Diseases 0.000 claims description 25
• 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 claims description 25
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 24
• 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims description 22
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 20
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 19
• IGERFAHWSHDDHX-UHFFFAOYSA-N 1,3-dioxanyl Chemical group [CH]1OCCCO1 IGERFAHWSHDDHX-UHFFFAOYSA-N 0.000 claims description 18
• 125000001425 triazolyl group Chemical group 0.000 claims description 18
• 125000001424 substituent group Chemical group 0.000 claims description 17
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 17
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 16
• JPRPJUMQRZTTED-UHFFFAOYSA-N 1,3-dioxolanyl Chemical group [CH]1OCCO1 JPRPJUMQRZTTED-UHFFFAOYSA-N 0.000 claims description 15
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 13
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 13
• 125000002837 carbocyclic group Chemical group 0.000 claims description 13
• 239000003814 drug Substances 0.000 claims description 13
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 13
• 239000000137 peptide hydrolase inhibitor Substances 0.000 claims description 13
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 12
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 12
• 125000001072 heteroaryl group Chemical group 0.000 claims description 11
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 11
• CBVCZFGXHXORBI-PXQQMZJSSA-N indinavir Chemical compound C([C@H](N(CC1)C[C@@H](O)C[C@@H](CC=2C=CC=CC=2)C(=O)N[C@H]2C3=CC=CC=C3C[C@H]2O)C(=O)NC(C)(C)C)N1CC1=CC=CN=C1 CBVCZFGXHXORBI-PXQQMZJSSA-N 0.000 claims description 11
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 11
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 11
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 10
• 125000004432 carbon atom Chemical group C* 0.000 claims description 10
• 229960001936 indinavir Drugs 0.000 claims description 10
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 9
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 9
• 229940124158 Protease/peptidase inhibitor Drugs 0.000 claims description 9
• 125000004104 aryloxy group Chemical group 0.000 claims description 9
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 9
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 9
• 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 8
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 8
• 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 8
• 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 8
• YMARZQAQMVYCKC-OEMFJLHTSA-N amprenavir Chemical compound C([C@@H]([C@H](O)CN(CC(C)C)S(=O)(=O)C=1C=CC(N)=CC=1)NC(=O)O[C@@H]1COCC1)C1=CC=CC=C1 YMARZQAQMVYCKC-OEMFJLHTSA-N 0.000 claims description 8
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 8
• WHBIGIKBNXZKFE-UHFFFAOYSA-N delavirdine Chemical compound CC(C)NC1=CC=CN=C1N1CCN(C(=O)C=2NC3=CC=C(NS(C)(=O)=O)C=C3C=2)CC1 WHBIGIKBNXZKFE-UHFFFAOYSA-N 0.000 claims description 8
• 229910052736 halogen Inorganic materials 0.000 claims description 8
• 239000004030 hiv protease inhibitor Substances 0.000 claims description 8
• QAGYKUNXZHXKMR-HKWSIXNMSA-N nelfinavir Chemical compound CC1=C(O)C=CC=C1C(=O)N[C@H]([C@H](O)CN1[C@@H](C[C@@H]2CCCC[C@@H]2C1)C(=O)NC(C)(C)C)CSC1=CC=CC=C1 QAGYKUNXZHXKMR-HKWSIXNMSA-N 0.000 claims description 8
• NQDJXKOVJZTUJA-UHFFFAOYSA-N nevirapine Chemical compound C12=NC=CC=C2C(=O)NC=2C(C)=CC=NC=2N1C1CC1 NQDJXKOVJZTUJA-UHFFFAOYSA-N 0.000 claims description 8
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 7
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 7
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 7
• QAGYKUNXZHXKMR-UHFFFAOYSA-N CPD000469186 Natural products CC1=C(O)C=CC=C1C(=O)NC(C(O)CN1C(CC2CCCCC2C1)C(=O)NC(C)(C)C)CSC1=CC=CC=C1 QAGYKUNXZHXKMR-UHFFFAOYSA-N 0.000 claims description 7
• XPOQHMRABVBWPR-UHFFFAOYSA-N Efavirenz Natural products O1C(=O)NC2=CC=C(Cl)C=C2C1(C(F)(F)F)C#CC1CC1 XPOQHMRABVBWPR-UHFFFAOYSA-N 0.000 claims description 7
• 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 7
• 239000003937 drug carrier Substances 0.000 claims description 7
• 229960003804 efavirenz Drugs 0.000 claims description 7
• XPOQHMRABVBWPR-ZDUSSCGKSA-N efavirenz Chemical compound C([C@]1(C2=CC(Cl)=CC=C2NC(=O)O1)C(F)(F)F)#CC1CC1 XPOQHMRABVBWPR-ZDUSSCGKSA-N 0.000 claims description 7
• 150000002367 halogens Chemical class 0.000 claims description 7
• 238000004519 manufacturing process Methods 0.000 claims description 7
• 229960000884 nelfinavir Drugs 0.000 claims description 7
• 102100035875 C-C chemokine receptor type 5 Human genes 0.000 claims description 6
• 101710149870 C-C chemokine receptor type 5 Proteins 0.000 claims description 6
• NCDNCNXCDXHOMX-UHFFFAOYSA-N Ritonavir Natural products C=1C=CC=CC=1CC(NC(=O)OCC=1SC=NC=1)C(O)CC(CC=1C=CC=CC=1)NC(=O)C(C(C)C)NC(=O)N(C)CC1=CSC(C(C)C)=N1 NCDNCNXCDXHOMX-UHFFFAOYSA-N 0.000 claims description 6
• ZGDKVKUWTCGYOA-URGPHPNLSA-N [4-[4-[(z)-c-(4-bromophenyl)-n-ethoxycarbonimidoyl]piperidin-1-yl]-4-methylpiperidin-1-yl]-(2,4-dimethyl-1-oxidopyridin-1-ium-3-yl)methanone Chemical compound C=1C=C(Br)C=CC=1C(=N/OCC)\C(CC1)CCN1C(CC1)(C)CCN1C(=O)C1=C(C)C=C[N+]([O-])=C1C ZGDKVKUWTCGYOA-URGPHPNLSA-N 0.000 claims description 6
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
• 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 6
• 229960000311 ritonavir Drugs 0.000 claims description 6
• NCDNCNXCDXHOMX-XGKFQTDJSA-N ritonavir Chemical compound N([C@@H](C(C)C)C(=O)N[C@H](C[C@H](O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1SC=NC=1)CC=1C=CC=CC=1)C(=O)N(C)CC1=CSC(C(C)C)=N1 NCDNCNXCDXHOMX-XGKFQTDJSA-N 0.000 claims description 6
• 229960001852 saquinavir Drugs 0.000 claims description 6
• QWAXKHKRTORLEM-UGJKXSETSA-N saquinavir Chemical compound C([C@@H]([C@H](O)CN1C[C@H]2CCCC[C@H]2C[C@H]1C(=O)NC(C)(C)C)NC(=O)[C@H](CC(N)=O)NC(=O)C=1N=C2C=CC=CC2=CC=1)C1=CC=CC=C1 QWAXKHKRTORLEM-UGJKXSETSA-N 0.000 claims description 6
• SUJUHGSWHZTSEU-FYBSXPHGSA-N tipranavir Chemical compound C([C@@]1(CCC)OC(=O)C([C@H](CC)C=2C=C(NS(=O)(=O)C=3N=CC(=CC=3)C(F)(F)F)C=CC=2)=C(O)C1)CC1=CC=CC=C1 SUJUHGSWHZTSEU-FYBSXPHGSA-N 0.000 claims description 6
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 5
• 229910052760 oxygen Inorganic materials 0.000 claims description 5
• 229910052698 phosphorus Inorganic materials 0.000 claims description 5
• JFKIHXVQWVFSNI-FCJVTMLMSA-N (2r,3r,4r,5r,6r,7r)-3,6-bis[(3-aminophenyl)methoxy]-2,7-dibenzyl-1,1-dioxothiepane-4,5-diol Chemical compound NC1=CC=CC(CO[C@H]2[C@H](S(=O)(=O)[C@H](CC=3C=CC=CC=3)[C@H](OCC=3C=C(N)C=CC=3)[C@H](O)[C@H]2O)CC=2C=CC=CC=2)=C1 JFKIHXVQWVFSNI-FCJVTMLMSA-N 0.000 claims description 4
• ZUBPKHVCBGWWGO-NDEPHWFRSA-N (2s)-2-[2-(4-aminophenyl)ethyl]-5-[2-tert-butyl-4-(hydroxymethyl)-5-methylphenyl]sulfanyl-4-hydroxy-2-propan-2-yl-3h-pyran-6-one Chemical compound C([C@]1(C(C)C)OC(=O)C(SC=2C(=CC(CO)=C(C)C=2)C(C)(C)C)=C(O)C1)CC1=CC=C(N)C=C1 ZUBPKHVCBGWWGO-NDEPHWFRSA-N 0.000 claims description 4
• CUFQBQOBLVLKRF-RZDMPUFOSA-N (4r)-3-[(2s,3s)-2-hydroxy-3-[(3-hydroxy-2-methylbenzoyl)amino]-4-phenylbutanoyl]-5,5-dimethyl-n-[(2-methylphenyl)methyl]-1,3-thiazolidine-4-carboxamide Chemical compound CC1=CC=CC=C1CNC(=O)[C@@H]1C(C)(C)SCN1C(=O)[C@@H](O)[C@@H](NC(=O)C=1C(=C(O)C=CC=1)C)CC1=CC=CC=C1 CUFQBQOBLVLKRF-RZDMPUFOSA-N 0.000 claims description 4
• HINZVVDZPLARRP-YSVIXOAZSA-N (4r,5s,6s,7r)-1,3-bis[(3-aminophenyl)methyl]-4,7-dibenzyl-5,6-dihydroxy-1,3-diazepan-2-one;methanesulfonic acid Chemical compound CS(O)(=O)=O.CS(O)(=O)=O.NC1=CC=CC(CN2C(N(CC=3C=C(N)C=CC=3)[C@H](CC=3C=CC=CC=3)[C@H](O)[C@@H](O)[C@H]2CC=2C=CC=CC=2)=O)=C1 HINZVVDZPLARRP-YSVIXOAZSA-N 0.000 claims description 4
• 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 4
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 4
• HOCFDYZWQYGULA-UHFFFAOYSA-N 1-(5-bromopyridin-2-yl)-3-(2-pyridin-2-ylethyl)thiourea Chemical compound N1=CC(Br)=CC=C1NC(=S)NCCC1=CC=CC=N1 HOCFDYZWQYGULA-UHFFFAOYSA-N 0.000 claims description 4
• 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 4
• ILAYIAGXTHKHNT-UHFFFAOYSA-N 4-[4-(2,4,6-trimethyl-phenylamino)-pyrimidin-2-ylamino]-benzonitrile Chemical compound CC1=CC(C)=CC(C)=C1NC1=CC=NC(NC=2C=CC(=CC=2)C#N)=N1 ILAYIAGXTHKHNT-UHFFFAOYSA-N 0.000 claims description 4
• VIBQRYBYKVEMJI-YSIASYRMSA-N 4-[[(2s,3s)-4-[(4r)-4-(tert-butylcarbamoyl)-5,5-dimethyl-1,3-thiazolidin-3-yl]-3-hydroxy-4-oxo-1-phenylbutan-2-yl]amino]-2,2-dimethyl-4-oxobutanoic acid Chemical compound C1SC(C)(C)[C@@H](C(=O)NC(C)(C)C)N1C(=O)[C@@H](O)[C@@H](NC(=O)CC(C)(C)C(O)=O)CC1=CC=CC=C1 VIBQRYBYKVEMJI-YSIASYRMSA-N 0.000 claims description 4
• KJHKTHWMRKYKJE-SUGCFTRWSA-N Kaletra Chemical compound N1([C@@H](C(C)C)C(=O)N[C@H](C[C@H](O)[C@H](CC=2C=CC=CC=2)NC(=O)COC=2C(=CC=CC=2C)C)CC=2C=CC=CC=2)CCCNC1=O KJHKTHWMRKYKJE-SUGCFTRWSA-N 0.000 claims description 4
• NJBBLOIWMSYVCQ-VZTVMPNDSA-N Kynostatin 272 Chemical compound C([C@H](NC(=O)[C@@H](NC(=O)COC=1C2=CC=NC=C2C=CC=1)CSC)[C@H](O)C(=O)N1[C@@H](CSC1)C(=O)NC(C)(C)C)C1=CC=CC=C1 NJBBLOIWMSYVCQ-VZTVMPNDSA-N 0.000 claims description 4
• 229960001830 amprenavir Drugs 0.000 claims description 4
• 229960005319 delavirdine Drugs 0.000 claims description 4
• MLILORUFDVLTSP-UHFFFAOYSA-N emivirine Chemical compound O=C1NC(=O)N(COCC)C(CC=2C=CC=CC=2)=C1C(C)C MLILORUFDVLTSP-UHFFFAOYSA-N 0.000 claims description 4
• PYGWGZALEOIKDF-UHFFFAOYSA-N etravirine Chemical compound CC1=CC(C#N)=CC(C)=C1OC1=NC(NC=2C=CC(=CC=2)C#N)=NC(N)=C1Br PYGWGZALEOIKDF-UHFFFAOYSA-N 0.000 claims description 4
• 229960002049 etravirine Drugs 0.000 claims description 4
• MLBVMOWEQCZNCC-OEMFJLHTSA-N fosamprenavir Chemical compound C([C@@H]([C@H](OP(O)(O)=O)CN(CC(C)C)S(=O)(=O)C=1C=CC(N)=CC=1)NC(=O)O[C@@H]1COCC1)C1=CC=CC=C1 MLBVMOWEQCZNCC-OEMFJLHTSA-N 0.000 claims description 4
• 230000004927 fusion Effects 0.000 claims description 4
• 125000005843 halogen group Chemical group 0.000 claims description 4
• 108010075606 kynostatin 272 Proteins 0.000 claims description 4
• YRSMQXBXGMENSN-UHFFFAOYSA-N men 10979 Chemical compound S=C1N(C)C2=CC=CN=C2N(CC)C2=C1SC1=CC=CN=C21 YRSMQXBXGMENSN-UHFFFAOYSA-N 0.000 claims description 4
• 229960000689 nevirapine Drugs 0.000 claims description 4
• 229950006460 palinavir Drugs 0.000 claims description 4
• RXBWRFDZXRAEJT-SZNOJMITSA-N palinavir Chemical compound C([C@H](NC(=O)[C@@H](NC(=O)C=1N=C2C=CC=CC2=CC=1)C(C)C)[C@H](O)CN1[C@@H](C[C@@H](CC1)OCC=1C=CN=CC=1)C(=O)NC(C)(C)C)C1=CC=CC=C1 RXBWRFDZXRAEJT-SZNOJMITSA-N 0.000 claims description 4
• VCMJCVGFSROFHV-WZGZYPNHSA-N tenofovir disoproxil fumarate Chemical compound OC(=O)\C=C\C(O)=O.N1=CN=C2N(C[C@@H](C)OCP(=O)(OCOC(=O)OC(C)C)OCOC(=O)OC(C)C)C=NC2=C1N VCMJCVGFSROFHV-WZGZYPNHSA-N 0.000 claims description 4
• BEUUJDAEPJZWHM-COROXYKFSA-N tert-butyl n-[(2s,3s,5r)-3-hydroxy-6-[[(2s)-1-(2-methoxyethylamino)-3-methyl-1-oxobutan-2-yl]amino]-6-oxo-1-phenyl-5-[(2,3,4-trimethoxyphenyl)methyl]hexan-2-yl]carbamate Chemical compound C([C@@H]([C@@H](O)C[C@H](C(=O)N[C@H](C(=O)NCCOC)C(C)C)CC=1C(=C(OC)C(OC)=CC=1)OC)NC(=O)OC(C)(C)C)C1=CC=CC=C1 BEUUJDAEPJZWHM-COROXYKFSA-N 0.000 claims description 4
• 238000002560 therapeutic procedure Methods 0.000 claims description 4
• 229950000977 trovirdine Drugs 0.000 claims description 4
• CNPVJJQCETWNEU-CYFREDJKSA-N (4,6-dimethyl-5-pyrimidinyl)-[4-[(3S)-4-[(1R)-2-methoxy-1-[4-(trifluoromethyl)phenyl]ethyl]-3-methyl-1-piperazinyl]-4-methyl-1-piperidinyl]methanone Chemical compound N([C@@H](COC)C=1C=CC(=CC=1)C(F)(F)F)([C@H](C1)C)CCN1C(CC1)(C)CCN1C(=O)C1=C(C)N=CN=C1C CNPVJJQCETWNEU-CYFREDJKSA-N 0.000 claims description 3
• XIOLHMQYEOSBMC-UHFFFAOYSA-N 7-fluoro-5-(propoxymethyl)-5-(trifluoromethyl)-2,10-dihydrobenzo[b][1,7]naphthyridin-1-one Chemical compound C1=CNC(=O)C2=C1C(COCCC)(C(F)(F)F)C1=CC(F)=CC=C1N2 XIOLHMQYEOSBMC-UHFFFAOYSA-N 0.000 claims description 3
• 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 3
• AYXBAIULRDEVAS-UHFFFAOYSA-N dimethyl-[[4-[[3-(4-methylphenyl)-8,9-dihydro-7h-benzo[7]annulene-6-carbonyl]amino]phenyl]methyl]-(oxan-4-yl)azanium;iodide Chemical compound [I-].C1=CC(C)=CC=C1C1=CC=C(CCCC(=C2)C(=O)NC=3C=CC(C[N+](C)(C)C4CCOCC4)=CC=3)C2=C1 AYXBAIULRDEVAS-UHFFFAOYSA-N 0.000 claims description 3
• 229940125777 fusion inhibitor Drugs 0.000 claims description 3
• UGVWSIZOYHUBHV-UHFFFAOYSA-N 5-[(butan-2-ylamino)methyl]-7-fluoro-2-methyl-5-(trifluoromethyl)-10h-benzo[b][1,7]naphthyridin-1-one Chemical compound N1C2=CC=C(F)C=C2C(CNC(C)CC)(C(F)(F)F)C2=C1C(=O)N(C)C=C2 UGVWSIZOYHUBHV-UHFFFAOYSA-N 0.000 claims description 2
• IZSVWTXABLOFDV-UHFFFAOYSA-N 7-fluoro-2-methyl-5-[(6-methylpyridin-2-yl)methyl]-5-(trifluoromethyl)-10h-benzo[b][1,7]naphthyridin-1-one Chemical compound CC1=CC=CC(CC2(C3=CC(F)=CC=C3NC=3C(=O)N(C)C=CC=32)C(F)(F)F)=N1 IZSVWTXABLOFDV-UHFFFAOYSA-N 0.000 claims description 2
• MSXNEQODZKXNOC-UHFFFAOYSA-N 7-fluoro-5-(2-pyrrolidin-1-ylethyl)-5-(trifluoromethyl)-2,10-dihydrobenzo[b][1,7]naphthyridin-1-one Chemical compound C12=CC(F)=CC=C2NC(C(NC=C2)=O)=C2C1(C(F)(F)F)CCN1CCCC1 MSXNEQODZKXNOC-UHFFFAOYSA-N 0.000 claims description 2
• RLDDWRGRUOEFEX-UHFFFAOYSA-N 7-fluoro-5-(pyridin-2-ylmethyl)-5-(trifluoromethyl)-2,10-dihydrobenzo[b][1,7]naphthyridin-1-one Chemical compound C12=CC(F)=CC=C2NC(C(NC=C2)=O)=C2C1(C(F)(F)F)CC1=CC=CC=N1 RLDDWRGRUOEFEX-UHFFFAOYSA-N 0.000 claims description 2
• KMIWJJNQIIMZHN-UHFFFAOYSA-N 7-fluoro-5-(pyridin-4-ylmethyl)-5-(trifluoromethyl)-2,10-dihydrobenzo[b][1,7]naphthyridin-1-one Chemical compound C12=CC(F)=CC=C2NC(C(NC=C2)=O)=C2C1(C(F)(F)F)CC1=CC=NC=C1 KMIWJJNQIIMZHN-UHFFFAOYSA-N 0.000 claims description 2
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