ZA200405139B - Tricyclic 2-pyrimidone compounds useful as HIV reverse transcriptase inhibitors. - Google Patents
Tricyclic 2-pyrimidone compounds useful as HIV reverse transcriptase inhibitors. Download PDFInfo
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- ZA200405139B ZA200405139B ZA200405139A ZA200405139A ZA200405139B ZA 200405139 B ZA200405139 B ZA 200405139B ZA 200405139 A ZA200405139 A ZA 200405139A ZA 200405139 A ZA200405139 A ZA 200405139A ZA 200405139 B ZA200405139 B ZA 200405139B
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- ZA
- South Africa
- Prior art keywords
- substituted
- group
- alkyl
- pharmaceutically acceptable
- compound
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- 239000003419 rna directed dna polymerase inhibitor Substances 0.000 title claims description 27
- 108010078851 HIV Reverse Transcriptase Proteins 0.000 title claims description 17
- 150000008319 1H-pyrimidin-2-ones Chemical class 0.000 title description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 86
- 150000001875 compounds Chemical class 0.000 claims description 86
- -1 phenylaminocarbonyl Chemical group 0.000 claims description 55
- 125000003545 alkoxy group Chemical group 0.000 claims description 48
- 229910052731 fluorine Inorganic materials 0.000 claims description 46
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 45
- 229910052801 chlorine Inorganic materials 0.000 claims description 44
- 238000000034 method Methods 0.000 claims description 37
- 239000000203 mixture Substances 0.000 claims description 37
- 150000003839 salts Chemical group 0.000 claims description 35
- 229910052739 hydrogen Inorganic materials 0.000 claims description 33
- 229910052794 bromium Inorganic materials 0.000 claims description 30
- 229910052740 iodine Inorganic materials 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
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 25
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 25
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 24
- 229910052757 nitrogen Inorganic materials 0.000 claims description 24
- 229910052760 oxygen Inorganic materials 0.000 claims description 24
- 229910052717 sulfur Inorganic materials 0.000 claims description 24
- 229910052799 carbon Inorganic materials 0.000 claims description 23
- 125000003342 alkenyl group Chemical group 0.000 claims description 22
- 125000000304 alkynyl group Chemical group 0.000 claims description 21
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 20
- 125000005842 heteroatom Chemical group 0.000 claims description 20
- 239000003112 inhibitor 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
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 18
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 17
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 15
- 125000000623 heterocyclic group Chemical group 0.000 claims description 14
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 12
- 239000003814 drug Substances 0.000 claims description 11
- 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims description 10
- IGERFAHWSHDDHX-UHFFFAOYSA-N 1,3-dioxanyl Chemical group [CH]1OCCCO1 IGERFAHWSHDDHX-UHFFFAOYSA-N 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
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 10
- 102100035875 C-C chemokine receptor type 5 Human genes 0.000 claims description 10
- 101710149870 C-C chemokine receptor type 5 Proteins 0.000 claims description 10
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 239000000137 peptide hydrolase inhibitor Substances 0.000 claims description 10
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 10
- JPRPJUMQRZTTED-UHFFFAOYSA-N 1,3-dioxolanyl Chemical group [CH]1OCCO1 JPRPJUMQRZTTED-UHFFFAOYSA-N 0.000 claims description 9
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 9
- 239000004030 hiv protease inhibitor Substances 0.000 claims description 9
- 229960001936 indinavir Drugs 0.000 claims description 9
- 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 9
- 125000001425 triazolyl group Chemical group 0.000 claims description 9
- 229940124158 Protease/peptidase inhibitor Drugs 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 8
- 230000004927 fusion Effects 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- 239000003937 drug carrier Substances 0.000 claims description 7
- 125000001072 heteroaryl group Chemical group 0.000 claims description 7
- HETSDWRDICBRSQ-UHFFFAOYSA-N 3h-quinolin-4-one Chemical compound C1=CC=C2C(=O)CC=NC2=C1 HETSDWRDICBRSQ-UHFFFAOYSA-N 0.000 claims description 6
- 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 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
- 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
- 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
- 229960003804 efavirenz Drugs 0.000 claims description 6
- 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 6
- 125000001188 haloalkyl group Chemical group 0.000 claims description 6
- 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 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
- 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
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- 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
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 5
- 125000002534 ethynyl group Chemical group [H]C#C* 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
- 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
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
- 125000005199 aryl carbonyloxy group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims description 4
- 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 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
- 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 claims description 4
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
- 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 3
- 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
- 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
- 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
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- 102000003886 Glycoproteins Human genes 0.000 description 5
- 108090000288 Glycoproteins Proteins 0.000 description 5
- HBOMLICNUCNMMY-XLPZGREQSA-N zidovudine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](N=[N+]=[N-])C1 HBOMLICNUCNMMY-XLPZGREQSA-N 0.000 description 5
- AVRPFRMDMNDIDH-UHFFFAOYSA-N 1h-quinazolin-2-one Chemical class C1=CC=CC2=NC(O)=NC=C21 AVRPFRMDMNDIDH-UHFFFAOYSA-N 0.000 description 4
- 108020004414 DNA Proteins 0.000 description 4
- 108020000999 Viral RNA Proteins 0.000 description 4
- 238000013518 transcription Methods 0.000 description 4
- 230000035897 transcription Effects 0.000 description 4
- 230000003612 virological effect Effects 0.000 description 4
- 108091032973 (ribonucleotides)n+m Proteins 0.000 description 3
- HQQTZCPKNZVLFF-UHFFFAOYSA-N 4h-1,2-benzoxazin-3-one Chemical class C1=CC=C2ONC(=O)CC2=C1 HQQTZCPKNZVLFF-UHFFFAOYSA-N 0.000 description 3
- 102000053602 DNA Human genes 0.000 description 3
- 108010010369 HIV Protease Proteins 0.000 description 3
- 108020005202 Viral DNA Proteins 0.000 description 3
- 210000000987 immune system Anatomy 0.000 description 3
- 108090000623 proteins and genes Proteins 0.000 description 3
- 150000008318 pyrimidones Chemical class 0.000 description 3
- JTEGQNOMFQHVDC-RQJHMYQMSA-N 4-amino-1-[(2s,5r)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]pyrimidin-2-one Chemical compound O=C1N=C(N)C=CN1[C@@H]1O[C@H](CO)SC1 JTEGQNOMFQHVDC-RQJHMYQMSA-N 0.000 description 2
- 206010001513 AIDS related complex Diseases 0.000 description 2
- 210000004366 CD4-positive T-lymphocyte Anatomy 0.000 description 2
- 102000004163 DNA-directed RNA polymerases Human genes 0.000 description 2
- 108090000626 DNA-directed RNA polymerases Proteins 0.000 description 2
- BXZVVICBKDXVGW-NKWVEPMBSA-N Didanosine Chemical compound O1[C@H](CO)CC[C@@H]1N1C(NC=NC2=O)=C2N=C1 BXZVVICBKDXVGW-NKWVEPMBSA-N 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- 108010076039 Polyproteins Proteins 0.000 description 2
- WREGKURFCTUGRC-POYBYMJQSA-N Zalcitabine Chemical compound O=C1N=C(N)C=CN1[C@@H]1O[C@H](CO)CC1 WREGKURFCTUGRC-POYBYMJQSA-N 0.000 description 2
- 239000003443 antiviral agent Substances 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 108010027225 gag-pol Fusion Proteins Proteins 0.000 description 2
- 230000001506 immunosuppresive effect Effects 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 229940042402 non-nucleoside reverse transcriptase inhibitor Drugs 0.000 description 2
- 239000002726 nonnucleoside reverse transcriptase inhibitor Substances 0.000 description 2
- 239000002777 nucleoside Substances 0.000 description 2
- 150000003833 nucleoside derivatives Chemical class 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 229940002612 prodrug Drugs 0.000 description 2
- 239000000651 prodrug Substances 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 230000010076 replication Effects 0.000 description 2
- 238000009007 Diagnostic Kit Methods 0.000 description 1
- 241000713772 Human immunodeficiency virus 1 Species 0.000 description 1
- 241000713340 Human immunodeficiency virus 2 Species 0.000 description 1
- 206010062016 Immunosuppression Diseases 0.000 description 1
- 208000001388 Opportunistic Infections Diseases 0.000 description 1
- 108020004682 Single-Stranded DNA Proteins 0.000 description 1
- XNKLLVCARDGLGL-JGVFFNPUSA-N Stavudine Chemical compound O=C1NC(=O)C(C)=CN1[C@H]1C=C[C@@H](CO)O1 XNKLLVCARDGLGL-JGVFFNPUSA-N 0.000 description 1
- 210000001744 T-lymphocyte Anatomy 0.000 description 1
- 108010067390 Viral Proteins Proteins 0.000 description 1
- 208000036142 Viral infection Diseases 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 238000011914 asymmetric synthesis Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000011461 current therapy Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 210000005260 human cell Anatomy 0.000 description 1
- 230000028993 immune response Effects 0.000 description 1
- 230000000899 immune system response Effects 0.000 description 1
- 239000002955 immunomodulating agent Substances 0.000 description 1
- 229940121354 immunomodulator Drugs 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 230000002147 killing effect Effects 0.000 description 1
- 210000004698 lymphocyte Anatomy 0.000 description 1
- 210000002540 macrophage Anatomy 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 108020004999 messenger RNA Proteins 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 125000005017 substituted alkenyl group Chemical group 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000004426 substituted alkynyl group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 241001430294 unidentified retrovirus Species 0.000 description 1
- 230000029812 viral genome replication Effects 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
- 230000017613 viral reproduction Effects 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
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Virology (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- AIDS & HIV (AREA)
- Engineering & Computer Science (AREA)
- Tropical Medicine & Parasitology (AREA)
- Molecular Biology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US34964102P | 2002-01-18 | 2002-01-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200405139B true ZA200405139B (en) | 2006-02-22 |
Family
ID=27613304
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200405139A ZA200405139B (en) | 2002-01-18 | 2004-06-28 | Tricyclic 2-pyrimidone compounds useful as HIV reverse transcriptase inhibitors. |
Country Status (21)
| Country | Link |
|---|---|
| US (2) | US6844340B2 (fr) |
| EP (1) | EP1474424A4 (fr) |
| JP (1) | JP2005519910A (fr) |
| KR (1) | KR20040077735A (fr) |
| CN (1) | CN1642954A (fr) |
| AR (1) | AR038164A1 (fr) |
| BR (1) | BR0306927A (fr) |
| CA (1) | CA2473420A1 (fr) |
| CO (1) | CO5590961A2 (fr) |
| HR (1) | HRP20040643A2 (fr) |
| IL (1) | IL162743A0 (fr) |
| IS (1) | IS7341A (fr) |
| MX (1) | MXPA04006948A (fr) |
| NO (1) | NO20043424L (fr) |
| PE (1) | PE20030987A1 (fr) |
| PL (1) | PL371418A1 (fr) |
| RU (1) | RU2004125151A (fr) |
| TW (1) | TW200306192A (fr) |
| WO (1) | WO2003062238A1 (fr) |
| YU (1) | YU62504A (fr) |
| ZA (1) | ZA200405139B (fr) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7169932B2 (en) | 2001-06-11 | 2007-01-30 | Pfizer Inc. | HIV protease inhibitors, compositions containing the same, their pharmaceutical uses, material for their synthesis |
| US7094909B2 (en) | 2001-06-11 | 2006-08-22 | Agouron Pharmaceuticals, Inc. | HIV protease inhibitors, compositions containing the same, their pharmaceutical uses and materials for their synthesis |
| HN2002000136A (es) | 2001-06-11 | 2003-07-31 | Basf Ag | Inhibidores de la proteasa del virus hiv, compuestos que contienen a los mismos, sus usos farmaceuticos y los materiales para su sintesis |
| 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 |
| US20070021449A1 (en) | 2003-02-07 | 2007-01-25 | Jan Heeres | Pyrimidine derivatives for the prevention of hiv infection |
| WO2008004100A2 (fr) | 2006-07-05 | 2008-01-10 | Pfizer Products Inc. | Composés thérapeutiques |
| US20080119552A1 (en) * | 2006-11-17 | 2008-05-22 | Novus International Inc. | Matrix-embedded compositions having organic acids and fatty acids |
| JP5406215B2 (ja) | 2008-01-25 | 2014-02-05 | ハイ ポイント ファーマシューティカルズ，リミティド ライアビリティ カンパニー | ＴＮＦ−α合成の調節因子及びＰＤＥ４阻害剤としての三環系化合物 |
| US20120316161A1 (en) | 2009-12-23 | 2012-12-13 | Katholieke Universiteit Leuven | Novel antiviral compounds |
| EP2640705A2 (fr) | 2010-11-15 | 2013-09-25 | Katholieke Universiteit Leuven | Nouveaux composés antiviraux |
| CA2817896A1 (fr) | 2010-11-15 | 2012-05-24 | Viiv Healthcare Uk Limited | Inhibiteurs de la replication du vih |
| CN103130787B (zh) * | 2011-11-24 | 2015-06-10 | 南开大学 | 嘧啶酮酰胺类化合物及其制备方法、抗hiv活性和抗tmv活性 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6593337B1 (en) * | 1999-10-19 | 2003-07-15 | Bristol-Myers Squibb Pharma Company | Tricyclic compounds useful as HIV reverse transcriptase inhibitors |
| US6596729B2 (en) | 2000-07-20 | 2003-07-22 | Bristol-Myers Squibb Company | Tricyclic-2-pyridone compounds useful as HIV reverse transcriptase inhibitors |
| TW200306192A (en) * | 2002-01-18 | 2003-11-16 | Bristol Myers Squibb Co | Tricyclic 2-pyrimidone compounds useful as HIV reverse transcriptase inhibitors |
-
2003
- 2003-01-14 TW TW092100706A patent/TW200306192A/zh unknown
- 2003-01-16 KR KR10-2004-7011080A patent/KR20040077735A/ko not_active Application Discontinuation
- 2003-01-16 MX MXPA04006948A patent/MXPA04006948A/es unknown
- 2003-01-16 RU RU2004125151/04A patent/RU2004125151A/ru not_active Application Discontinuation
- 2003-01-16 JP JP2003562115A patent/JP2005519910A/ja not_active Withdrawn
- 2003-01-16 YU YU62504A patent/YU62504A/sh unknown
- 2003-01-16 IL IL16274303A patent/IL162743A0/xx unknown
- 2003-01-16 CA CA002473420A patent/CA2473420A1/fr not_active Abandoned
- 2003-01-16 PL PL03371418A patent/PL371418A1/xx not_active Application Discontinuation
- 2003-01-16 CN CNA038060566A patent/CN1642954A/zh active Pending
- 2003-01-16 BR BR0306927-3A patent/BR0306927A/pt not_active IP Right Cessation
- 2003-01-16 WO PCT/US2003/001604 patent/WO2003062238A1/fr not_active Application Discontinuation
- 2003-01-16 EP EP03702165A patent/EP1474424A4/fr not_active Withdrawn
- 2003-01-17 US US10/346,613 patent/US6844340B2/en not_active Expired - Lifetime
- 2003-01-17 AR ARP030100142A patent/AR038164A1/es not_active Application Discontinuation
- 2003-01-20 PE PE2003000060A patent/PE20030987A1/es not_active Application Discontinuation
-
2004
- 2004-06-28 ZA ZA200405139A patent/ZA200405139B/en unknown
- 2004-06-30 IS IS7341A patent/IS7341A/is unknown
- 2004-07-13 HR HR20040643A patent/HRP20040643A2/hr not_active Application Discontinuation
- 2004-07-15 US US10/891,974 patent/US7186830B2/en not_active Expired - Lifetime
- 2004-07-16 CO CO04068142A patent/CO5590961A2/es not_active Application Discontinuation
- 2004-08-17 NO NO20043424A patent/NO20043424L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| IL162743A0 (en) | 2005-11-20 |
| US7186830B2 (en) | 2007-03-06 |
| NO20043424L (no) | 2004-08-18 |
| CA2473420A1 (fr) | 2003-07-31 |
| US20030162800A1 (en) | 2003-08-28 |
| US20040266778A1 (en) | 2004-12-30 |
| PE20030987A1 (es) | 2003-11-15 |
| HRP20040643A2 (en) | 2005-04-30 |
| BR0306927A (pt) | 2004-11-09 |
| TW200306192A (en) | 2003-11-16 |
| RU2004125151A (ru) | 2006-02-20 |
| CO5590961A2 (es) | 2005-12-30 |
| EP1474424A4 (fr) | 2005-12-28 |
| WO2003062238A1 (fr) | 2003-07-31 |
| CN1642954A (zh) | 2005-07-20 |
| EP1474424A1 (fr) | 2004-11-10 |
| YU62504A (sh) | 2006-08-17 |
| IS7341A (is) | 2004-06-30 |
| PL371418A1 (en) | 2005-06-13 |
| KR20040077735A (ko) | 2004-09-06 |
| MXPA04006948A (es) | 2004-12-06 |
| JP2005519910A (ja) | 2005-07-07 |
| AR038164A1 (es) | 2004-12-29 |
| US6844340B2 (en) | 2005-01-18 |
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