SK392003A3 - Tricyclic 2-pyridone compounds useful as HIV reverse transcriptase inhibitors - Google Patents
Tricyclic 2-pyridone compounds useful as HIV reverse transcriptase inhibitors Download PDFInfo
- Publication number
- SK392003A3 SK392003A3 SK39-2003A SK392003A SK392003A3 SK 392003 A3 SK392003 A3 SK 392003A3 SK 392003 A SK392003 A SK 392003A SK 392003 A3 SK392003 A3 SK 392003A3
- Authority
- SK
- Slovakia
- Prior art keywords
- group
- trifluoromethyl
- substituted
- alkyl
- dihydrobenzo
- Prior art date
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- 108010078851 HIV Reverse Transcriptase Proteins 0.000 title claims abstract description 19
- 239000003419 rna directed dna polymerase inhibitor Substances 0.000 title claims description 23
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical class OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 title abstract description 8
- 239000000203 mixture Substances 0.000 claims abstract description 70
- 238000000034 method Methods 0.000 claims abstract description 48
- 150000003839 salts Chemical group 0.000 claims abstract description 33
- 239000003112 inhibitor Substances 0.000 claims abstract description 16
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 7
- 150000001875 compounds Chemical class 0.000 claims description 275
- -1 phenylaminocarbonyl Chemical group 0.000 claims description 216
- 239000000460 chlorine Substances 0.000 claims description 167
- 125000000217 alkyl group Chemical group 0.000 claims description 158
- 229910052739 hydrogen Inorganic materials 0.000 claims description 136
- 229910052799 carbon Inorganic materials 0.000 claims description 118
- 229910052801 chlorine Inorganic materials 0.000 claims description 81
- 229910052757 nitrogen Inorganic materials 0.000 claims description 81
- 125000003545 alkoxy group Chemical group 0.000 claims description 77
- 229910052731 fluorine Inorganic materials 0.000 claims description 74
- 229910052794 bromium Inorganic materials 0.000 claims description 53
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 51
- 229910052740 iodine Inorganic materials 0.000 claims description 49
- 229910052760 oxygen Inorganic materials 0.000 claims description 49
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 46
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 42
- 125000005842 heteroatom Chemical group 0.000 claims description 39
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 37
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 34
- 125000000623 heterocyclic group Chemical group 0.000 claims description 34
- 229910052717 sulfur Inorganic materials 0.000 claims description 33
- 125000000304 alkynyl group Chemical group 0.000 claims description 30
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 29
- 125000003342 alkenyl group Chemical group 0.000 claims description 26
- 208000031886 HIV Infections Diseases 0.000 claims description 22
- 208000037357 HIV infectious disease Diseases 0.000 claims description 22
- 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 claims description 22
- 238000011282 treatment Methods 0.000 claims description 22
- 239000003814 drug Substances 0.000 claims description 20
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 20
- 125000003118 aryl group Chemical group 0.000 claims description 19
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 19
- 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 19
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 18
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 17
- JPRPJUMQRZTTED-UHFFFAOYSA-N 1,3-dioxolanyl Chemical group [CH]1OCCO1 JPRPJUMQRZTTED-UHFFFAOYSA-N 0.000 claims description 16
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 16
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 16
- 125000004434 sulfur atom Chemical group 0.000 claims description 16
- IGERFAHWSHDDHX-UHFFFAOYSA-N 1,3-dioxanyl Chemical group [CH]1OCCCO1 IGERFAHWSHDDHX-UHFFFAOYSA-N 0.000 claims description 15
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 15
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 14
- 125000001425 triazolyl 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
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 13
- 125000006569 (C5-C6) heterocyclic group Chemical group 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 12
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 11
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 10
- 125000001072 heteroaryl group Chemical group 0.000 claims description 10
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 9
- 125000006479 2-pyridyl methyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 9
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 9
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 9
- 125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 claims description 8
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 8
- 239000004030 hiv protease inhibitor Substances 0.000 claims description 8
- 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 8
- 239000001301 oxygen Substances 0.000 claims description 8
- 239000000137 peptide hydrolase inhibitor Substances 0.000 claims description 8
- 150000003254 radicals Chemical class 0.000 claims description 8
- 125000004104 aryloxy group Chemical group 0.000 claims description 7
- 125000004122 cyclic group Chemical group 0.000 claims description 7
- 229960001936 indinavir Drugs 0.000 claims description 7
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 6
- 125000006432 1-methyl cyclopropyl group Chemical group [H]C([H])([H])C1(*)C([H])([H])C1([H])[H] 0.000 claims description 6
- 125000006017 1-propenyl group Chemical group 0.000 claims description 6
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 6
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 6
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 6
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 6
- ACQQFGZRNMUBKS-UHFFFAOYSA-N 7-chloro-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(Cl)=CC=C1N2 ACQQFGZRNMUBKS-UHFFFAOYSA-N 0.000 claims description 6
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 6
- 229940124158 Protease/peptidase inhibitor Drugs 0.000 claims description 6
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 6
- 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 6
- 125000005199 aryl carbonyloxy group Chemical group 0.000 claims description 6
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims description 6
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
- 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 6
- 239000003937 drug carrier Substances 0.000 claims description 6
- 125000001188 haloalkyl group Chemical group 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 claims description 6
- NQDJXKOVJZTUJA-UHFFFAOYSA-N nevirapine Chemical compound C12=NC=CC=C2C(=O)NC=2C(C)=CC=NC=2N1C1CC1 NQDJXKOVJZTUJA-UHFFFAOYSA-N 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
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 5
- 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 5
- 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 5
- 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 5
- 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 5
- 229960003804 efavirenz Drugs 0.000 claims description 5
- 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 5
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 5
- KELNNWMENBUHNS-NSHDSACASA-N isopropyl (2s)-2-ethyl-7-fluoro-3-oxo-3,4-dihydroquinoxaline-1(2h)-carboxylate Chemical compound FC1=CC=C2NC(=O)[C@H](CC)N(C(=O)OC(C)C)C2=C1 KELNNWMENBUHNS-NSHDSACASA-N 0.000 claims description 5
- 229960000884 nelfinavir Drugs 0.000 claims description 5
- 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 5
- 229960001852 saquinavir Drugs 0.000 claims description 5
- 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 5
- GTJITGRMVXRBTD-UHFFFAOYSA-N 5-(2-ethoxyethyl)-7-fluoro-5-(trifluoromethyl)-2,10-dihydrobenzo[b][1,7]naphthyridin-1-one Chemical compound C1=CNC(=O)C2=C1C(CCOCC)(C(F)(F)F)C1=CC(F)=CC=C1N2 GTJITGRMVXRBTD-UHFFFAOYSA-N 0.000 claims description 4
- MTBRNCBAGVNNBH-UHFFFAOYSA-N 5-butyl-7-fluoro-5-(trifluoromethyl)-2,10-dihydrobenzo[b][1,7]naphthyridin-1-one Chemical compound N1C2=CC=C(F)C=C2C(CCCC)(C(F)(F)F)C2=C1C(=O)NC=C2 MTBRNCBAGVNNBH-UHFFFAOYSA-N 0.000 claims description 4
- AMJVKELEMDKYDS-UHFFFAOYSA-N 7-fluoro-5-(2-methoxyethyl)-5-(trifluoromethyl)-2,10-dihydrobenzo[b][1,7]naphthyridin-1-one Chemical compound N1C2=CC=C(F)C=C2C(CCOC)(C(F)(F)F)C2=C1C(=O)NC=C2 AMJVKELEMDKYDS-UHFFFAOYSA-N 0.000 claims description 4
- 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 4
- 102100035875 C-C chemokine receptor type 5 Human genes 0.000 claims description 4
- 101710149870 C-C chemokine receptor type 5 Proteins 0.000 claims description 4
- 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 4
- 230000004927 fusion Effects 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Natural products CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 4
- 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 3
- 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 3
- 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 3
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 3
- GWKIPRVERALPRD-ZDUSSCGKSA-N (s)-4-isopropoxycarbonyl-6-methoxy-3-methylthiomethyl-3,4-dihydroquinoxalin-2(1h)-thione Chemical compound N1C(=S)[C@H](CSC)N(C(=O)OC(C)C)C2=CC(OC)=CC=C21 GWKIPRVERALPRD-ZDUSSCGKSA-N 0.000 claims description 3
- 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 3
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 3
- BWIFRAYNFMNDNM-UHFFFAOYSA-N 3-chloro-7-fluoro-5-propyl-5-(trifluoromethyl)-2,10-dihydrobenzo[b][1,7]naphthyridin-1-one Chemical compound C1=C(Cl)NC(=O)C2=C1C(CCC)(C(F)(F)F)C1=CC(F)=CC=C1N2 BWIFRAYNFMNDNM-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 3
- 229960001830 amprenavir Drugs 0.000 claims description 3
- 229960005319 delavirdine Drugs 0.000 claims description 3
- 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 3
- 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 3
- 229960002049 etravirine Drugs 0.000 claims description 3
- 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 3
- 229960000689 nevirapine Drugs 0.000 claims description 3
- 229950006460 palinavir Drugs 0.000 claims description 3
- 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 3
- 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 3
- 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 3
- 238000002560 therapeutic procedure Methods 0.000 claims description 3
- 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 3
- 229950000977 trovirdine Drugs 0.000 claims description 3
- NIDRYBLTWYFCFV-FMTVUPSXSA-N (+)-calanolide A Chemical compound C1=CC(C)(C)OC2=C1C(O[C@H](C)[C@@H](C)[C@@H]1O)=C1C1=C2C(CCC)=CC(=O)O1 NIDRYBLTWYFCFV-FMTVUPSXSA-N 0.000 claims description 2
- 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 2
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- 125000001376 1,2,4-triazolyl group Chemical class N1N=C(N=C1)* 0.000 claims description 2
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- 239000011534 wash buffer Substances 0.000 description 1
- 230000003313 weakening effect Effects 0.000 description 1
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
- YZYKBQUWMPUVEN-UHFFFAOYSA-N zafuleptine Chemical compound OC(=O)CCCCCC(C(C)C)NCC1=CC=C(F)C=C1 YZYKBQUWMPUVEN-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
- A61K31/7052—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
- A61K31/706—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom
- A61K31/7064—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines
- A61K31/7068—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines having oxo groups directly attached to the pyrimidine ring, e.g. cytidine, cytidylic acid
- A61K31/7072—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines having oxo groups directly attached to the pyrimidine ring, e.g. cytidine, cytidylic acid having two oxo groups directly attached to the pyrimidine ring, e.g. uridine, uridylic acid, thymidine, zidovudine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Molecular Biology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Virology (AREA)
- Engineering & Computer Science (AREA)
- AIDS & HIV (AREA)
- Tropical Medicine & Parasitology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US21953200P | 2000-07-20 | 2000-07-20 | |
US28485601P | 2001-04-19 | 2001-04-19 | |
PCT/US2001/022827 WO2002008226A2 (en) | 2000-07-20 | 2001-07-20 | Tricyclic 2-pyridone compounds useful as hiv reverse transcriptase inhibitors |
Publications (1)
Publication Number | Publication Date |
---|---|
SK392003A3 true SK392003A3 (en) | 2003-10-07 |
Family
ID=26913986
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
SK39-2003A SK392003A3 (en) | 2000-07-20 | 2001-07-20 | Tricyclic 2-pyridone compounds useful as HIV reverse transcriptase inhibitors |
Country Status (23)
Country | Link |
---|---|
US (1) | US6596729B2 (sl) |
EP (1) | EP1303515A2 (sl) |
JP (1) | JP2004532793A (sl) |
KR (1) | KR20030065454A (sl) |
CN (1) | CN1464878A (sl) |
AR (1) | AR031861A1 (sl) |
AU (1) | AU2001280641A1 (sl) |
BG (1) | BG107439A (sl) |
BR (1) | BR0112606A (sl) |
CA (1) | CA2418194A1 (sl) |
EE (1) | EE200300027A (sl) |
HU (1) | HUP0302862A2 (sl) |
IL (1) | IL153683A0 (sl) |
IS (1) | IS6690A (sl) |
LT (1) | LT2003003A (sl) |
LV (1) | LV13024B (sl) |
MX (1) | MXPA03000434A (sl) |
NO (1) | NO20030248L (sl) |
PL (1) | PL365958A1 (sl) |
SI (1) | SI21139A (sl) |
SK (1) | SK392003A3 (sl) |
WO (1) | WO2002008226A2 (sl) |
YU (1) | YU3203A (sl) |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7638522B2 (en) | 2001-08-13 | 2009-12-29 | Janssen Pharmaceutica N.V. | Salt of 4-[[4-[[4-(2-cyanoethenyl)-2,6-dimethylphenyl]amino]-2-pyrimidinyl]amino] benzonitrile |
US8101629B2 (en) | 2001-08-13 | 2012-01-24 | Janssen Pharmaceutica N.V. | Salt of 4-[[4-[[4-(2-cyanoethenyl)-2,6-dimethylphenyl]amino]-2-pyrimidinyl]amino]benzonitrile |
JO3429B1 (ar) | 2001-08-13 | 2019-10-20 | Janssen Pharmaceutica Nv | مشتقات برميدينات مثبطة فيروس الايدز |
TW200306192A (en) | 2002-01-18 | 2003-11-16 | Bristol Myers Squibb Co | Tricyclic 2-pyrimidone compounds useful as HIV reverse transcriptase inhibitors |
AR039540A1 (es) | 2002-05-13 | 2005-02-23 | Tibotec Pharm Ltd | Compuestos microbicidas con contenido de pirimidina o triazina |
CA2493794C (en) | 2002-08-09 | 2010-05-25 | Janssen Pharmaceutica N.V. | Processes for the preparation of 4-[[4-[[4-(2-cyanoethenyl)-2,6-dimethylphenyl]amino]-2-pyrimidinyl]amino]benzonitrile |
CL2004000192A1 (es) | 2003-02-07 | 2005-03-18 | Janssen Pharmaceutica Nv | Uso de compuestos derivados de 2-aminopirimidina para preparar un medicamento para la prevencion de una infeccion por vih relaciones sexuales o un contacto intimo en la pareja. |
CA2564027A1 (en) * | 2004-05-17 | 2005-11-24 | Tibotec Pharmaceuticals Ltd. | 1-heterocyclyl-1,5-dihydro-pyrido[3,2-b]indol-2-ones |
Family Cites Families (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3700673A (en) * | 1971-02-12 | 1972-10-24 | Morton Norwich Products Inc | 3-4-dihydrobenzo(b) (1,7)naphthyridin-1(2h)-ones |
GB9023289D0 (en) | 1990-10-25 | 1990-12-05 | Ici Plc | Herbicides |
IL102764A0 (en) | 1991-08-16 | 1993-01-31 | Merck & Co Inc | Quinazoline derivatives,and pharmaceutical compositions containing them |
WO1993004047A1 (en) * | 1991-08-16 | 1993-03-04 | Merck & Co., Inc. | Quinazoline derivatives as inhibitors of hiv reverse transcriptase |
DE4320347A1 (de) | 1993-06-19 | 1994-12-22 | Boehringer Mannheim Gmbh | Quinazolin-Derivate und diese enthaltende Arzneimittel |
WO1995012583A1 (en) | 1993-11-05 | 1995-05-11 | Merck & Co., Inc. | New quinazolines as inhibitors of hiv reverse transcriptase |
DE4344452A1 (de) | 1993-12-24 | 1995-06-29 | Hoechst Ag | Aza-4-iminochinoline, Verfahren zu ihrer Herstellung und ihre Verwendung |
ID18046A (id) | 1996-08-20 | 1998-02-19 | Takeda Chemical Industries Ltd | Senyawa siklik campuran, pembuatan dan penngunaannya. |
CA2268953A1 (en) | 1996-10-02 | 1998-04-09 | Du Pont Pharmaceuticals Company | 4,4-disubstituted-1,4-dihydro-2h-3,1-benzoxazin-2-ones useful as hiv reverse transcriptase inhibitors and intermediates and processes for making the same |
HRP980143A2 (en) | 1997-04-09 | 1999-02-28 | Soo Sung Ko | 4,4-disubstituted-3,4-dihydro-2 (1h)-quinazolinones useful as hiv reverse transcriptase inhibitors |
US6593337B1 (en) | 1999-10-19 | 2003-07-15 | Bristol-Myers Squibb Pharma Company | Tricyclic compounds useful as HIV reverse transcriptase inhibitors |
-
2001
- 2001-07-19 US US09/908,995 patent/US6596729B2/en not_active Expired - Lifetime
- 2001-07-20 CA CA002418194A patent/CA2418194A1/en not_active Abandoned
- 2001-07-20 SI SI200120050A patent/SI21139A/sl not_active IP Right Cessation
- 2001-07-20 EP EP01959047A patent/EP1303515A2/en not_active Withdrawn
- 2001-07-20 JP JP2002514132A patent/JP2004532793A/ja active Pending
- 2001-07-20 AU AU2001280641A patent/AU2001280641A1/en not_active Abandoned
- 2001-07-20 KR KR10-2003-7000800A patent/KR20030065454A/ko not_active Application Discontinuation
- 2001-07-20 AR ARP010103492A patent/AR031861A1/es unknown
- 2001-07-20 HU HU0302862A patent/HUP0302862A2/hu unknown
- 2001-07-20 YU YU3203A patent/YU3203A/sh unknown
- 2001-07-20 BR BR0112606-7A patent/BR0112606A/pt not_active Application Discontinuation
- 2001-07-20 EE EEP200300027A patent/EE200300027A/xx unknown
- 2001-07-20 WO PCT/US2001/022827 patent/WO2002008226A2/en not_active Application Discontinuation
- 2001-07-20 CN CN01815629A patent/CN1464878A/zh active Pending
- 2001-07-20 SK SK39-2003A patent/SK392003A3/sk unknown
- 2001-07-20 MX MXPA03000434A patent/MXPA03000434A/es unknown
- 2001-07-20 PL PL01365958A patent/PL365958A1/xx not_active Application Discontinuation
- 2001-07-20 IL IL15368301A patent/IL153683A0/xx unknown
-
2003
- 2003-01-06 BG BG107439A patent/BG107439A/bg unknown
- 2003-01-15 LT LT2003003A patent/LT2003003A/xx not_active Application Discontinuation
- 2003-01-17 NO NO20030248A patent/NO20030248L/no not_active Application Discontinuation
- 2003-01-17 IS IS6690A patent/IS6690A/is unknown
- 2003-02-18 LV LVP-03-16A patent/LV13024B/en unknown
Also Published As
Publication number | Publication date |
---|---|
LV13024B (en) | 2003-10-20 |
BR0112606A (pt) | 2004-06-29 |
AR031861A1 (es) | 2003-10-08 |
KR20030065454A (ko) | 2003-08-06 |
JP2004532793A (ja) | 2004-10-28 |
BG107439A (bg) | 2003-09-30 |
US20020107261A1 (en) | 2002-08-08 |
CA2418194A1 (en) | 2002-01-31 |
US6596729B2 (en) | 2003-07-22 |
NO20030248L (no) | 2003-03-17 |
IS6690A (is) | 2003-01-17 |
SI21139A (sl) | 2003-08-31 |
AU2001280641A1 (en) | 2002-02-05 |
IL153683A0 (en) | 2003-07-06 |
LT2003003A (en) | 2003-11-25 |
PL365958A1 (en) | 2005-01-24 |
YU3203A (sh) | 2006-01-16 |
EP1303515A2 (en) | 2003-04-23 |
WO2002008226A3 (en) | 2002-06-20 |
MXPA03000434A (es) | 2003-06-24 |
EE200300027A (et) | 2004-10-15 |
HUP0302862A2 (hu) | 2003-12-29 |
NO20030248D0 (no) | 2003-01-17 |
CN1464878A (zh) | 2003-12-31 |
WO2002008226A2 (en) | 2002-01-31 |
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