IL115944A - Composition for the treatment of hiv-1 infection containing a heterocyclyl carb (ox/thio) anilide derivative - Google Patents

Composition for the treatment of hiv-1 infection containing a heterocyclyl carb (ox/thio) anilide derivative

Info

Publication number: IL115944A
Authority: IL; Israel
Prior art keywords: hiv; alkyl; hydrogen; branched; composition
Prior art date: 1994-11-30

Application number

IL11594495A

Other languages

English (en)

Other versions

IL115944A0 (en

Original Assignee

Rega Inst For Medical Res

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1994-11-30

Filing date

1995-11-09

Publication date

2001-10-31

1995-11-09 Application filed by Rega Inst For Medical Res filed Critical Rega Inst For Medical Res

1995-11-09 Priority to IL14022495A priority Critical patent/IL140224A/en

1996-05-14 Publication of IL115944A0 publication Critical patent/IL115944A0/xx

2000-12-11 Priority to IL14022400A priority patent/IL140224A0/xx

2001-10-31 Publication of IL115944A publication Critical patent/IL115944A/en

Links

239000000203 mixture Substances 0.000 title claims abstract description 35
208000031886 HIV Infections Diseases 0.000 title claims abstract description 11
238000011282 treatment Methods 0.000 title claims abstract description 11
125000000623 heterocyclic group Chemical group 0.000 title claims abstract description 7
125000000446 sulfanediyl group Chemical group *S* 0.000 title description 3
150000003931 anilides Chemical class 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 131
239000003112 inhibitor Substances 0.000 claims abstract description 105
241000713772 Human immunodeficiency virus 1 Species 0.000 claims abstract description 97
125000000217 alkyl group Chemical group 0.000 claims abstract description 56
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 47
239000001257 hydrogen Substances 0.000 claims abstract description 47
241000725303 Human immunodeficiency virus Species 0.000 claims abstract description 26
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 20
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 17
150000002431 hydrogen Chemical group 0.000 claims abstract description 15
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 15
125000004122 cyclic group Chemical group 0.000 claims abstract description 14
229910052736 halogen Inorganic materials 0.000 claims abstract description 14
150000002367 halogens Chemical group 0.000 claims abstract description 14
125000004001 thioalkyl group Chemical group 0.000 claims abstract description 13
125000004385 trihaloalkyl group Chemical group 0.000 claims abstract description 13
125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 12
125000000304 alkynyl group Chemical group 0.000 claims abstract description 10
125000001188 haloalkyl group Chemical group 0.000 claims abstract description 10
125000005020 hydroxyalkenyl group Chemical group 0.000 claims abstract description 10
125000005016 hydroxyalkynyl group Chemical group 0.000 claims abstract description 10
125000003342 alkenyl group Chemical group 0.000 claims abstract description 9
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 9
230000002265 prevention Effects 0.000 claims abstract description 9
125000004414 alkyl thio group Chemical group 0.000 claims abstract description 8
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 7
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims abstract description 7
125000004103 aminoalkyl group Chemical group 0.000 claims abstract description 7
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims abstract description 5
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 5
125000005041 acyloxyalkyl group Chemical group 0.000 claims abstract description 4
125000003302 alkenyloxy group Chemical group 0.000 claims abstract description 4
125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 4
125000000278 alkyl amino alkyl group Chemical group 0.000 claims abstract description 4
125000006350 alkyl thio alkyl group Chemical group 0.000 claims abstract description 4
125000005133 alkynyloxy group Chemical group 0.000 claims abstract description 4
125000004181 carboxyalkyl group Chemical group 0.000 claims abstract description 4
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 4
125000004985 dialkyl amino alkyl group Chemical group 0.000 claims abstract description 4
125000002541 furyl group Chemical group 0.000 claims abstract description 4
125000004415 heterocyclylalkyl group Chemical group 0.000 claims abstract description 4
125000002757 morpholinyl group Chemical group 0.000 claims abstract description 4
125000003566 oxetanyl group Chemical group 0.000 claims abstract description 4
125000000466 oxiranyl group Chemical group 0.000 claims abstract description 4
125000004193 piperazinyl group Chemical group 0.000 claims abstract description 4
125000000719 pyrrolidinyl group Chemical group 0.000 claims abstract description 4
125000003718 tetrahydrofuranyl group Chemical group 0.000 claims abstract description 4
125000001412 tetrahydropyranyl group Chemical group 0.000 claims abstract description 4
125000004953 trihalomethyl group Chemical group 0.000 claims abstract description 4
239000002777 nucleoside Substances 0.000 claims abstract description 3
150000003833 nucleoside derivatives Chemical class 0.000 claims abstract description 3
125000003386 piperidinyl group Chemical group 0.000 claims abstract description 3
229910052760 oxygen Inorganic materials 0.000 claims abstract 3
229910052717 sulfur Inorganic materials 0.000 claims abstract 3
-1 C7-C12 alkarylalkyl Chemical group 0.000 claims description 17
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
125000003545 alkoxy group Chemical group 0.000 claims description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
229910014585 C2-Ce Inorganic materials 0.000 claims 1
125000003710 aryl alkyl group Chemical group 0.000 claims 1
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 abstract description 3
125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 4
125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 3
125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 abstract 2
125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
KIWSYRHAAPLJFJ-DNZSEPECSA-N n-[(e,2z)-4-ethyl-2-hydroxyimino-5-nitrohex-3-enyl]pyridine-3-carboxamide Chemical compound [O-][N+](=O)C(C)C(/CC)=C/C(=N/O)/CNC(=O)C1=CC=CN=C1 KIWSYRHAAPLJFJ-DNZSEPECSA-N 0.000 abstract 1
108010092799 RNA-directed DNA polymerase Proteins 0.000 description 125
102100034343 Integrase Human genes 0.000 description 123
241000700605 Viruses Species 0.000 description 38
NQDJXKOVJZTUJA-UHFFFAOYSA-N nevirapine Chemical compound C12=NC=CC=C2C(=O)NC=2C(C)=CC=NC=2N1C1CC1 NQDJXKOVJZTUJA-UHFFFAOYSA-N 0.000 description 33
238000004113 cell culture Methods 0.000 description 21
230000035772 mutation Effects 0.000 description 18
229960000689 nevirapine Drugs 0.000 description 16
OBTZDIRUQWFRFZ-UHFFFAOYSA-N 2-(5-methylfuran-2-yl)-n-(4-methylphenyl)quinoline-4-carboxamide Chemical compound O1C(C)=CC=C1C1=CC(C(=O)NC=2C=CC(C)=CC=2)=C(C=CC=C2)C2=N1 OBTZDIRUQWFRFZ-UHFFFAOYSA-N 0.000 description 15
230000002401 inhibitory effect Effects 0.000 description 13
KZKYYGSZDVZKNJ-XDSPWSPCSA-N 1-[(5r,6r,8r,9r)-4-amino-9-[tert-butyl(dimethyl)silyl]oxy-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,2-dioxo-1,7-dioxa-2$l^{6}-thiaspiro[4.4]non-3-en-8-yl]-3,5-dimethylpyrimidine-2,4-dione Chemical compound O=C1N(C)C(=O)C(C)=CN1[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)[C@@]2(C(=CS(=O)(=O)O2)N)[C@@H](CO[Si](C)(C)C(C)(C)C)O1 KZKYYGSZDVZKNJ-XDSPWSPCSA-N 0.000 description 10
239000003814 drug Substances 0.000 description 10
UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 10
235000008529 Ziziphus vulgaris Nutrition 0.000 description 9
244000126002 Ziziphus vulgaris Species 0.000 description 9
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125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 8
WTTIBCHOELPGFK-LBPRGKRZSA-N r82150 Chemical compound C1N(CC=C(C)C)[C@@H](C)CN2C(=S)NC3=CC=CC1=C32 WTTIBCHOELPGFK-LBPRGKRZSA-N 0.000 description 8
230000035945 sensitivity Effects 0.000 description 8
150000001413 amino acids Chemical group 0.000 description 7
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 7
230000000694 effects Effects 0.000 description 7
208000015181 infectious disease Diseases 0.000 description 7
KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 6
239000004480 active ingredient Substances 0.000 description 6
RCSLUNOLLUVOOG-NSHDSACASA-N 4-chloro-8-methyl-7-(3-methyl-but-2-enyl)-6,7,8,9-tetrahydro-2h-2,7,9a-triaza-benzo[cd]azulene-1-thione Chemical compound C1N(CC=C(C)C)[C@@H](C)CN2C(=S)NC3=CC(Cl)=CC1=C32 RCSLUNOLLUVOOG-NSHDSACASA-N 0.000 description 5
238000002474 experimental method Methods 0.000 description 5
238000001228 spectrum Methods 0.000 description 5
238000013337 sub-cultivation Methods 0.000 description 5
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 4
239000000890 drug combination Substances 0.000 description 4
238000000034 method Methods 0.000 description 4
239000000047 product Substances 0.000 description 4
XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 4
108091034117 Oligonucleotide Proteins 0.000 description 3
JLCPHMBAVCMARE-UHFFFAOYSA-N [3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methyl [5-(6-aminopurin-9-yl)-2-(hydroxymethyl)oxolan-3-yl] hydrogen phosphate Polymers Cc1cn(C2CC(OP(O)(=O)OCC3OC(CC3OP(O)(=O)OCC3OC(CC3O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c3nc(N)[nH]c4=O)C(COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3CO)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cc(C)c(=O)[nH]c3=O)n3cc(C)c(=O)[nH]c3=O)n3ccc(N)nc3=O)n3cc(C)c(=O)[nH]c3=O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)O2)c(=O)[nH]c1=O JLCPHMBAVCMARE-UHFFFAOYSA-N 0.000 description 3
230000000840 anti-viral effect Effects 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
230000003111 delayed effect Effects 0.000 description 3
230000002939 deleterious effect Effects 0.000 description 3
239000004615 ingredient Substances 0.000 description 3
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230000001566 pro-viral effect Effects 0.000 description 3
230000000717 retained effect Effects 0.000 description 3
239000000758 substrate Substances 0.000 description 3
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150000003852 triazoles Chemical class 0.000 description 3
125000006656 (C2-C4) alkenyl group Chemical group 0.000 description 2
125000006650 (C2-C4) alkynyl group Chemical group 0.000 description 2
QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 2
UMQCVRJLQBUADZ-UHFFFAOYSA-N 3-[4-[3-(propan-2-ylamino)pyridin-2-yl]piperazin-1-yl]indol-2-one Chemical compound CC(C)NC1=CC=CN=C1N1CCN(C=2C(N=C3C=CC=CC3=2)=O)CC1 UMQCVRJLQBUADZ-UHFFFAOYSA-N 0.000 description 2
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TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
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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
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
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125000004448 alkyl carbonyl group Chemical group 0.000 description 2
239000012228 culture supernatant Substances 0.000 description 2
HAAZLUGHYHWQIW-KVQBGUIXSA-N dGTP Chemical compound C1=NC=2C(=O)NC(N)=NC=2N1[C@H]1C[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)O1 HAAZLUGHYHWQIW-KVQBGUIXSA-N 0.000 description 2
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RWSXRVCMGQZWBV-WDSKDSINSA-N glutathione Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O RWSXRVCMGQZWBV-WDSKDSINSA-N 0.000 description 2
239000001963 growth medium Substances 0.000 description 2
230000001524 infective effect Effects 0.000 description 2
230000002452 interceptive effect Effects 0.000 description 2
CJPLEFFCVDQQFZ-UHFFFAOYSA-N loviride Chemical compound CC(=O)C1=CC=C(C)C=C1NC(C(N)=O)C1=C(Cl)C=CC=C1Cl CJPLEFFCVDQQFZ-UHFFFAOYSA-N 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
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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 description 1
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HDMHBHNRWDNNCD-UHFFFAOYSA-N 1-[(2-hydroxyethoxy)methyl]-6-(phenylsulfanyl)thymine Chemical class OCCOCN1C(=O)NC(=O)C(C)=C1SC1=CC=CC=C1 HDMHBHNRWDNNCD-UHFFFAOYSA-N 0.000 description 1
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SCVJRXQHFJXZFZ-KVQBGUIXSA-N 2-amino-9-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3h-purine-6-thione Chemical compound C1=2NC(N)=NC(=S)C=2N=CN1[C@H]1C[C@H](O)[C@@H](CO)O1 SCVJRXQHFJXZFZ-KVQBGUIXSA-N 0.000 description 1
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NIDRYBLTWYFCFV-UHFFFAOYSA-N calanolide F Natural products C1=CC(C)(C)OC2=C1C(OC(C)C(C)C1O)=C1C1=C2C(CCC)=CC(=O)O1 NIDRYBLTWYFCFV-UHFFFAOYSA-N 0.000 description 1
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VHJLVAABSRFDPM-QWWZWVQMSA-N dithiothreitol Chemical compound SC[C@@H](O)[C@H](O)CS VHJLVAABSRFDPM-QWWZWVQMSA-N 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
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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 description 1
NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
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238000009472 formulation Methods 0.000 description 1
229960003180 glutathione Drugs 0.000 description 1
125000001072 heteroaryl group Chemical group 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
238000011534 incubation Methods 0.000 description 1
230000000977 initiatory effect Effects 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
230000003993 interaction Effects 0.000 description 1
JTEGQNOMFQHVDC-NKWVEPMBSA-N lamivudine Chemical compound O=C1N=C(N)C=CN1[C@H]1O[C@@H](CO)SC1 JTEGQNOMFQHVDC-NKWVEPMBSA-N 0.000 description 1
229910001629 magnesium chloride Inorganic materials 0.000 description 1
239000000463 material Substances 0.000 description 1
ZSUMCRSGZQLTDK-UHFFFAOYSA-N n-phenyloxathiine-3-carboxamide Chemical class C=1C=COSC=1C(=O)NC1=CC=CC=C1 ZSUMCRSGZQLTDK-UHFFFAOYSA-N 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
238000003199 nucleic acid amplification method Methods 0.000 description 1
AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
239000002245 particle Substances 0.000 description 1
239000008177 pharmaceutical agent Substances 0.000 description 1
238000003752 polymerase chain reaction Methods 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
150000005299 pyridinones Chemical class 0.000 description 1
238000002976 reverse transcriptase assay Methods 0.000 description 1
238000012163 sequencing technique Methods 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000007921 spray Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
210000001541 thymus gland Anatomy 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
230000003612 virological effect Effects 0.000 description 1
229960000523 zalcitabine Drugs 0.000 description 1

Classifications

- 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
- 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
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants

Landscapes

Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
Medicinal Chemistry (AREA)
Chemical & Material Sciences (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Immunology (AREA)
Virology (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Communicable Diseases (AREA)
Epidemiology (AREA)
Oncology (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
AIDS & HIV (AREA)
Tropical Medicine & Parasitology (AREA)
Molecular Biology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

IL11594495A 1994-11-30 1995-11-09 Composition for the treatment of hiv-1 infection containing a heterocyclyl carb (ox/thio) anilide derivative IL115944A (en)

Priority Applications (2)

Application Number	Priority Date	Filing Date	Title
IL14022495A IL140224A (en)	1994-11-30	1995-11-09	Composition for the treatment of hiv-1 infection containing a heterocyclyl carb (ox/thio) anilide derivative
IL14022400A IL140224A0 (en)	1994-11-30	2000-12-11	A composition for the treatment of hiv-1 infection containing a heterocyclyl carb (ox/thio) anilide derivative

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US08/346,721 US5968910A (en)	1994-11-30	1994-11-30	Compositions containing two or three inhibitors of different HIV reverse transcriptases

Publications (2)

Publication Number	Publication Date
IL115944A0 IL115944A0 (en)	1996-05-14
IL115944A true IL115944A (en)	2001-10-31

Family

ID=23360750

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL11594495A IL115944A (en)	1994-11-30	1995-11-09	Composition for the treatment of hiv-1 infection containing a heterocyclyl carb (ox/thio) anilide derivative

Country Status (16)

Country	Link
US (1)	US5968910A (de)
EP (1)	EP0794793B1 (de)
JP (1)	JP3655636B2 (de)
KR (1)	KR100403545B1 (de)
CN (1)	CN1104909C (de)
AU (1)	AU717025B2 (de)
BR (1)	BR9509925A (de)
CA (1)	CA2204652C (de)
DE (1)	DE69535366T2 (de)
HU (1)	HU223548B1 (de)
IL (1)	IL115944A (de)
MX (1)	MX9704024A (de)
NZ (1)	NZ297006A (de)
RU (1)	RU2227750C2 (de)
WO (1)	WO1996016675A2 (de)
ZA (1)	ZA9510108B (de)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5696151A (en) *	1995-11-30	1997-12-09	Uniroyal Chemical Company, Inc.	Compounds useful for the inhibition of the replication of HIV-1 and HIV-1 mutants
WO1999008110A1 (en) *	1997-08-08	1999-02-18	Newbiotics, Inc.	Methods and compositions for overcoming resistance to biologic and chemotherapy
IL137164A0 (en)	1998-01-23	2001-07-24	Newbiotics Inc	Enzyme catalyzed therapeutic agents
US7462605B2 (en) *	1998-01-23	2008-12-09	Celmed Oncology (Usa), Inc.	Phosphoramidate compounds and methods of use
US6683061B1 (en) *	1999-07-22	2004-01-27	Newbiotics, Inc.	Enzyme catalyzed therapeutic activation
BR0012676A (pt)	1999-07-22	2003-07-01	Newbiotics Inc	Métodos para tratamento de tumores resistentes a terapia
WO2001021160A2 (en) *	1999-09-23	2001-03-29	Axxima Pharmaceuticals Aktiengesellschaft	Carboxymide and aniline derivatives as selective inhibitors of pathogens
UA74826C2 (en) *	2000-05-17	2006-02-15	Ortho Mcneil Pharm Inc	?-carboline derivatives as phosphodiesterase inhibitors
CN101108178B (zh) *	2006-07-20	2010-09-15	复旦大学	一种亲环素a抑制剂在制备抗艾滋病药物中的应用

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5047407A (en) *	1989-02-08	1991-09-10	Iaf Biochem International, Inc.	2-substituted-5-substituted-1,3-oxathiolanes with antiviral properties
US5268389A (en) *	1989-10-16	1993-12-07	Uniroyal Chemical Company, Inc.	Thiocarboxylate ester compounds compositions containing the same
IL99843A0 (en) *	1990-11-01	1992-08-18	Merck & Co Inc	Synergistic combination of hiv reverse transcriptase inhibitors
DE69120069T2 (de) *	1991-09-04	1996-10-02	Consejo Superior Investigacion	Substituierte Nukleosidderivate, Verfahren zu ihrer Herstellung und sie enthaltende pharmazeutische Zusammensetzungen

1994
- 1994-11-30 US US08/346,721 patent/US5968910A/en not_active Expired - Lifetime
1995
- 1995-11-09 IL IL11594495A patent/IL115944A/en not_active IP Right Cessation
- 1995-11-28 ZA ZA9510108A patent/ZA9510108B/xx unknown
- 1995-11-29 CA CA002204652A patent/CA2204652C/en not_active Expired - Lifetime
- 1995-11-29 AU AU41769/96A patent/AU717025B2/en not_active Expired
- 1995-11-29 KR KR1019970703579A patent/KR100403545B1/ko not_active Expired - Lifetime
- 1995-11-29 JP JP51818896A patent/JP3655636B2/ja not_active Expired - Fee Related
- 1995-11-29 WO PCT/EP1995/004704 patent/WO1996016675A2/en not_active Ceased
- 1995-11-29 BR BR9509925A patent/BR9509925A/pt not_active IP Right Cessation
- 1995-11-29 HU HU9800354A patent/HU223548B1/hu active IP Right Grant
- 1995-11-29 MX MX9704024A patent/MX9704024A/es unknown
- 1995-11-29 DE DE69535366T patent/DE69535366T2/de not_active Expired - Lifetime
- 1995-11-29 NZ NZ297006A patent/NZ297006A/en not_active IP Right Cessation
- 1995-11-29 RU RU97110670/15A patent/RU2227750C2/ru active
- 1995-11-29 EP EP95940258A patent/EP0794793B1/de not_active Expired - Lifetime
- 1995-11-29 CN CN95196540A patent/CN1104909C/zh not_active Expired - Lifetime

Also Published As

Publication number	Publication date
BR9509925A (pt)	1997-09-30
JPH10500996A (ja)	1998-01-27
ZA9510108B (en)	1996-06-06
JP3655636B2 (ja)	2005-06-02
HUT77573A (hu)	1998-06-29
CN1167442A (zh)	1997-12-10
DE69535366T2 (de)	2007-10-11
NZ297006A (en)	2001-03-30
AU4176996A (en)	1996-06-19
MX9704024A (es)	1998-02-28
KR987000088A (ko)	1998-03-30
CA2204652A1 (en)	1996-06-06
WO1996016675A3 (en)	1996-08-29
HU223548B1 (hu)	2004-09-28
DE69535366D1 (de)	2007-02-22
CN1104909C (zh)	2003-04-09
US5968910A (en)	1999-10-19
WO1996016675A2 (en)	1996-06-06
AU717025B2 (en)	2000-03-16
IL115944A0 (en)	1996-05-14
RU2227750C2 (ru)	2004-04-27
EP0794793A1 (de)	1997-09-17
CA2204652C (en)	2009-04-07
EP0794793B1 (de)	2007-01-10
KR100403545B1 (ko)	2004-05-27

Legal Events

Date	Code	Title
2002-05-23	KB	Patent renewed
2006-02-05	KB	Patent renewed
2010-05-17	KB	Patent renewed
2013-11-28	KB	Patent renewed
2016-06-30	EXP	Patent expired

Publication	Publication Date	Title
Pereira et al.	2004	Antiviral activity of diterpenes isolated from the Brazilian marine alga Dictyota menstrualis against human immunodeficiency virus type 1 (HIV-1)
Schinazi et al.	1993	Characterization of human immunodeficiency viruses resistant to oxathiolane-cytosine nucleosides
Richman et al.	1991	Human immunodeficiency virus type 1 mutants resistant to nonnucleoside inhibitors of reverse transcriptase arise in tissue culture.
Kleim et al.	1995	Preclinical evaluation of HBY 097, a new nonnucleoside reverse transcriptase inhibitor of human immunodeficiency virus type 1 replication
US11364242B2 (en)	2022-06-21	Treatment agents for inhibiting HIV and cancer in HIV infected patients
AU6951994A (en)	1994-12-20	New procedure to block the replication of reverse transcriptase dependent viruses by the use of inhibitors of deoxynucleotides synthesis
IL115944A (en)	2001-10-31	Composition for the treatment of hiv-1 infection containing a heterocyclyl carb (ox/thio) anilide derivative
MD3413897T2 (ro)	2023-11-30	Metode de tratament și profilaxie a HIV și SIDA
Bisset et al.	2002	Combined effect of zidovudine (ZDV), lamivudine (3TC) and abacavir (ABC) antiretroviral therapy in suppressing in vitro FIV replication
US9289445B2 (en)	2016-03-22	Compositions and methods for treating or preventing a retrovirus infection
Baba et al.	1995	Hept derivatives: 6-Benzyl-1-ethoxymethyl-5-isopropyluracil (MKC-442)
Balzarini et al.	1996	Marked inhibitory activity of non-nucleoside reverse transcriptase inhibitors against human immunodeficiency virus type 1 when combined with (-) 2', 3'-dideoxy-3'-thiacytidine.
MXPA97004024A (en)	1998-02-01	Composition and method for the prevention and treatment of infection with vi
Tanaka et al.	1997	In vitro induction of human immunodeficiency virus type 1 variants resistant to 2'-beta-Fluoro-2', 3'-dideoxyadenosine
Seki et al.	1995	Isolation and characterization of human immunodeficiency virus type-1 mutants resistant to the non-nucleotide reverse transcriptase inhibitor MKC-442
EP1159005B1 (de)	2003-11-12	Pharmazeutische kombination von antiviralen wirkstoffen
Cho et al.	2021	The frequency of defective genes in vif and vpr genes in 20 hemophiliacs is associated with Korean Red Ginseng and highly active antiretroviral therapy: the impact of lethal mutations in vif and vpr genes on HIV-1 evolution
Rübsamen-Waigmann et al.	1999	Resistance mutations selected in vivo under therapy with anti-HIV drug HBY 097 differ from resistance pattern selected in vitro
Zhang et al.	1997	Topotecan inhibits human immunodeficiency virus type 1 infection through a topoisomerase-independent mechanism in a cell line with altered topoisomerase I
IL140224A (en)	2004-12-15	Composition for the treatment of hiv-1 infection containing a heterocyclyl carb (ox/thio) anilide derivative
CN101564408A (zh)	2009-10-28	含有高丽人参的用于使HIV-1具有5’LTR/gag基因缺陷的药物组合物
Okamoto et al.	1996	Complete inhibition of viral breakthrough by combination of MKC-442 with AZT during a long-term culture of HIV-1-infected cells
Mansour	1996	Patent Update Anti-infectives: Emerging anti-HIV agents and targets
Feng et al.	2005	Effects of HIV Q151M-associated multi-drug resistance mutations on the activities of (−)-β-d-1′, 3′-dioxolan guanine
Gupta et al.	2007	AIDS: A review of targets and approaches for treatment.