ES2707997T3 - Compuestos de benzotiazol y su uso farmacéutico - Google Patents
Compuestos de benzotiazol y su uso farmacéutico Download PDFInfo
- Publication number
- ES2707997T3 ES2707997T3 ES16196723T ES16196723T ES2707997T3 ES 2707997 T3 ES2707997 T3 ES 2707997T3 ES 16196723 T ES16196723 T ES 16196723T ES 16196723 T ES16196723 T ES 16196723T ES 2707997 T3 ES2707997 T3 ES 2707997T3
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- ES
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- Prior art keywords
- alkyl
- carbocycle
- heterocycle
- heteroaryl
- aryl
- Prior art date
- Legal status (The legal status 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 status listed.)
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- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 title description 12
- 150000001875 compounds Chemical class 0.000 claims abstract description 251
- -1 (C3-C7) carbocycle Chemical group 0.000 claims abstract description 183
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 110
- 125000003118 aryl group Chemical group 0.000 claims abstract description 99
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 93
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 86
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 85
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 61
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims abstract description 52
- 150000003839 salts Chemical class 0.000 claims abstract description 48
- 125000005843 halogen group Chemical group 0.000 claims abstract description 41
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 31
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 30
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 21
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 19
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 13
- 125000004043 oxo group Chemical group O=* 0.000 claims abstract description 13
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims abstract description 10
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 8
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 7
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 6
- 150000002367 halogens Chemical class 0.000 claims abstract description 3
- 125000000464 thioxo group Chemical group S=* 0.000 claims abstract description 3
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims description 77
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- 229940124597 therapeutic agent Drugs 0.000 claims description 28
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- 229940079593 drug Drugs 0.000 claims description 16
- 239000008194 pharmaceutical composition Substances 0.000 claims description 16
- 208000037357 HIV infectious disease Diseases 0.000 claims description 15
- 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 claims description 15
- 241000124008 Mammalia Species 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 10
- 230000001225 therapeutic effect Effects 0.000 claims description 9
- 102100035875 C-C chemokine receptor type 5 Human genes 0.000 claims description 8
- 101710149870 C-C chemokine receptor type 5 Proteins 0.000 claims description 8
- 102100031650 C-X-C chemokine receptor type 4 Human genes 0.000 claims description 8
- 101000922348 Homo sapiens C-X-C chemokine receptor type 4 Proteins 0.000 claims description 8
- 239000002773 nucleotide Substances 0.000 claims description 8
- 125000003729 nucleotide group Chemical group 0.000 claims description 8
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- 239000003937 drug carrier Substances 0.000 claims description 3
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- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 claims 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 claims 1
- 235000009973 maize Nutrition 0.000 claims 1
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 abstract description 26
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 215
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- 238000002360 preparation method Methods 0.000 description 137
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 103
- 235000019439 ethyl acetate Nutrition 0.000 description 98
- 239000000203 mixture Substances 0.000 description 91
- 239000000243 solution Substances 0.000 description 88
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- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 62
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 58
- 238000005160 1H NMR spectroscopy Methods 0.000 description 57
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 54
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 53
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 50
- 238000006243 chemical reaction Methods 0.000 description 50
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 44
- 239000004480 active ingredient Substances 0.000 description 41
- 239000000741 silica gel Substances 0.000 description 38
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- 238000009472 formulation Methods 0.000 description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
- 238000005481 NMR spectroscopy Methods 0.000 description 35
- 241000725303 Human immunodeficiency virus Species 0.000 description 32
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- 229910052943 magnesium sulfate Inorganic materials 0.000 description 25
- 235000019341 magnesium sulphate Nutrition 0.000 description 25
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- 125000006239 protecting group Chemical group 0.000 description 20
- NPRYCHLHHVWLQZ-TURQNECASA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynylpurin-8-one Chemical compound NC1=NC=C2N(C(N(C2=N1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C NPRYCHLHHVWLQZ-TURQNECASA-N 0.000 description 19
- 241000183024 Populus tremula Species 0.000 description 19
- 235000017557 sodium bicarbonate Nutrition 0.000 description 18
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 18
- ZYZCALPXKGUGJI-DDVDASKDSA-M (e,3r,5s)-7-[3-(4-fluorophenyl)-2-phenyl-5-propan-2-ylimidazol-4-yl]-3,5-dihydroxyhept-6-enoate Chemical compound C=1C=C(F)C=CC=1N1C(\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O)=C(C(C)C)N=C1C1=CC=CC=C1 ZYZCALPXKGUGJI-DDVDASKDSA-M 0.000 description 17
- 239000012074 organic phase Substances 0.000 description 17
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 description 16
- 239000000047 product Substances 0.000 description 16
- 239000002253 acid Chemical group 0.000 description 15
- 239000000725 suspension Substances 0.000 description 15
- IUGYQRQAERSCNH-UHFFFAOYSA-M pivalate Chemical compound CC(C)(C)C([O-])=O IUGYQRQAERSCNH-UHFFFAOYSA-M 0.000 description 14
- 125000001424 substituent group Chemical group 0.000 description 14
- 238000003786 synthesis reaction Methods 0.000 description 13
- OGZMTYGAYGHOEL-UHFFFAOYSA-N 2-bromo-7-(4-chlorophenyl)-6-methoxy-5-methyl-1,3-benzothiazole Chemical compound COC1=C(C)C=C2N=C(Br)SC2=C1C1=CC=C(Cl)C=C1 OGZMTYGAYGHOEL-UHFFFAOYSA-N 0.000 description 12
- 108010078851 HIV Reverse Transcriptase Proteins 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 12
- 239000003921 oil Substances 0.000 description 12
- 235000019198 oils Nutrition 0.000 description 12
- 208000030507 AIDS Diseases 0.000 description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 11
- 125000004429 atom Chemical group 0.000 description 11
- 239000000543 intermediate Substances 0.000 description 11
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 11
- 239000000546 pharmaceutical excipient Substances 0.000 description 11
- 239000003826 tablet Substances 0.000 description 11
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- 239000002585 base Substances 0.000 description 10
- 238000004440 column chromatography Methods 0.000 description 10
- 125000004122 cyclic group Chemical group 0.000 description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 10
- 239000002777 nucleoside Substances 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- 229910052717 sulfur Chemical group 0.000 description 10
- 239000011593 sulfur Chemical group 0.000 description 10
- KJQUCTYWDHDJTQ-NRFANRHFSA-N (2s)-2-[7-(4-chlorophenyl)-5-methyl-2-(2-methylpropyl)-1,3-benzothiazol-6-yl]-2-[(2-methylpropan-2-yl)oxy]acetic acid Chemical compound C=12SC(CC(C)C)=NC2=CC(C)=C([C@H](OC(C)(C)C)C(O)=O)C=1C1=CC=C(Cl)C=C1 KJQUCTYWDHDJTQ-NRFANRHFSA-N 0.000 description 9
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- 229950010765 pivalate Drugs 0.000 description 9
- WGFNXGPBPIJYLI-UHFFFAOYSA-N 2,6-difluoro-3-[(3-fluorophenyl)sulfonylamino]-n-(3-methoxy-1h-pyrazolo[3,4-b]pyridin-5-yl)benzamide Chemical compound C1=C2C(OC)=NNC2=NC=C1NC(=O)C(C=1F)=C(F)C=CC=1NS(=O)(=O)C1=CC=CC(F)=C1 WGFNXGPBPIJYLI-UHFFFAOYSA-N 0.000 description 8
- LVCDPPSDHDLHRT-UHFFFAOYSA-N 6-methoxy-5-methyl-1,3-benzothiazol-2-amine Chemical compound C1=C(C)C(OC)=CC2=C1N=C(N)S2 LVCDPPSDHDLHRT-UHFFFAOYSA-N 0.000 description 8
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 8
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 8
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- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
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- LJPOULAKEXHSBK-LBPRGKRZSA-N ethyl (2s)-2-[2-bromo-5-methyl-7-(trifluoromethylsulfonyloxy)-1,3-benzothiazol-6-yl]-2-[(2-methylpropan-2-yl)oxy]acetate Chemical compound CCOC(=O)[C@@H](OC(C)(C)C)C1=C(C)C=C2N=C(Br)SC2=C1OS(=O)(=O)C(F)(F)F LJPOULAKEXHSBK-LBPRGKRZSA-N 0.000 description 8
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- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 8
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- 0 *C(*)(C(O)=O)c1c(*)c(*)c2nc(*)[s]c2c1* Chemical compound *C(*)(C(O)=O)c1c(*)c(*)c2nc(*)[s]c2c1* 0.000 description 7
- FJILDPNBUQDPHB-UHFFFAOYSA-N 7-(4-chlorophenyl)-5-methyl-2-(2-methylprop-1-enyl)-1,3-benzothiazol-6-ol Chemical compound C=12SC(C=C(C)C)=NC2=CC(C)=C(O)C=1C1=CC=C(Cl)C=C1 FJILDPNBUQDPHB-UHFFFAOYSA-N 0.000 description 7
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- NZEUOQMGCPNWKI-CYBMUJFWSA-N [(2s)-2-(7-bromo-3,5-dimethyl-2-oxo-1,3-benzothiazol-6-yl)-2-[(2-methylpropan-2-yl)oxy]ethyl] 2,2-dimethylpropanoate Chemical compound BrC1=C([C@@H](COC(=O)C(C)(C)C)OC(C)(C)C)C(C)=CC2=C1SC(=O)N2C NZEUOQMGCPNWKI-CYBMUJFWSA-N 0.000 description 7
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- HXVHCXAXDHRKFN-GFCCVEGCSA-N [(2s)-2-(7-bromo-2-chloro-5-methyl-1,3-benzothiazol-6-yl)-2-[(2-methylpropan-2-yl)oxy]ethyl] 2,2-dimethylpropanoate Chemical compound BrC1=C([C@@H](COC(=O)C(C)(C)C)OC(C)(C)C)C(C)=CC2=C1SC(Cl)=N2 HXVHCXAXDHRKFN-GFCCVEGCSA-N 0.000 description 6
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Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/06—Peri-condensed systems
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/428—Thiazoles condensed with carbocyclic rings
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- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4738—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems
- A61K31/4741—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems condensed with ring systems having oxygen as a ring hetero atom, e.g. tubocuraran derivatives, noscapine, bicuculline
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
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- C07D277/62—Benzothiazoles
- C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
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- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D277/82—Nitrogen atoms
-
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/08—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing alicyclic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/052—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being six-membered
Landscapes
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- Thiazole And Isothizaole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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| ES2615734T3 (es) | 2011-04-21 | 2017-06-08 | Gilead Sciences, Inc. | Compuestos de benzotiazol y su uso farmacéutico |
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| WO2015174511A1 (ja) | 2014-05-16 | 2015-11-19 | 塩野義製薬株式会社 | Hiv複製阻害作用を有する3環性複素環誘導体 |
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| US20160067255A1 (en) | 2014-09-04 | 2016-03-10 | Gilead Sciences, Inc. | Methods of treating or preventing hiv in patients using a combination of tenofovir alafenamide and dolutegravir |
| UY36298A (es) | 2014-09-16 | 2016-04-29 | Gilead Science Inc | Formas sólidas de un modulador del receptor tipo toll |
| TWI738321B (zh) | 2014-12-23 | 2021-09-01 | 美商基利科學股份有限公司 | 多環胺甲醯基吡啶酮化合物及其醫藥用途 |
| BR112017013491A2 (pt) | 2014-12-24 | 2018-01-09 | Gilead Sciences, Inc. | compostos de pirimidina fundida para o tratamento de hiv |
| TWI699355B (zh) | 2014-12-24 | 2020-07-21 | 美商基利科學股份有限公司 | 喹唑啉化合物 |
| NZ733125A (en) | 2014-12-24 | 2018-06-29 | Gilead Sciences Inc | Isoquinoline compounds for the treatment of hiv |
| LT3236972T (lt) | 2014-12-26 | 2021-11-10 | Emory University | Antivirusiniai n4-hidroksicitidino dariniai |
| EP3722297A1 (en) | 2015-03-04 | 2020-10-14 | Gilead Sciences, Inc. | Toll-like receptor modulating 4,6-diamino-pyrido[3,2-d]pyrimidine compounds |
| CA2980362C (en) | 2015-04-02 | 2020-02-25 | Gilead Sciences, Inc. | Polycyclic-carbamoylpyridone compounds and their pharmaceutical use |
| MA43120A (fr) | 2015-05-29 | 2018-09-05 | Shionogi & Co | Dérivé tricyclique contenant de l'azote présentant une activité inhibitrice de la réplication du vih |
| CA2995004A1 (en) | 2015-08-26 | 2017-03-02 | Gilead Sciences, Inc. | Deuterated toll-like receptor modulators |
| US20180263985A1 (en) | 2015-09-15 | 2018-09-20 | Gilead Sciences, Inc. | Modulators of toll-like receptors for the treatment of hiv |
| CA2999516A1 (en) | 2015-09-30 | 2017-04-06 | Gilead Sciences, Inc. | Compounds and combinations for the treatment of hiv |
| JP6732915B2 (ja) | 2015-12-15 | 2020-07-29 | ギリアード サイエンシーズ, インコーポレイテッド | ヒト免疫不全ウイルス中和抗体 |
| BR112018071678B1 (pt) | 2016-08-19 | 2021-01-26 | Gilead Sciences, Inc. | compostos terapêuticos úteis para o tratamento profilático ou terapêutico de uma infecção por vírus hiv e suas composições farmacêuticas |
| WO2018042332A1 (en) | 2016-08-31 | 2018-03-08 | Glaxosmithkline Intellectual Property (No.2) Limited | Combinations and uses and treatments thereof |
| WO2018042331A1 (en) | 2016-08-31 | 2018-03-08 | Glaxosmithkline Intellectual Property (No.2) Limited | Combinations and uses and treatments thereof |
| US10640499B2 (en) | 2016-09-02 | 2020-05-05 | Gilead Sciences, Inc. | Toll like receptor modulator compounds |
| ES2906581T3 (es) | 2016-09-02 | 2022-04-19 | Gilead Sciences Inc | Compuestos moduladores de los receptores tipo Toll |
| WO2018051250A1 (en) | 2016-09-14 | 2018-03-22 | Viiv Healthcare Company | Combination comprising tenofovir alafenamide, bictegravir and 3tc |
| US10800772B2 (en) | 2016-09-28 | 2020-10-13 | Gilead Sciences, Inc. | Therapeutic compounds |
| US10407438B2 (en) | 2016-10-27 | 2019-09-10 | Gilead Sciences, Inc. | Crystalline forms of darunavir |
| JP2020503348A (ja) | 2017-01-03 | 2020-01-30 | ヴィーブ ヘルスケア ユーケー(ナンバー5)リミテッド | ヒト免疫不全ウイルス複製の阻害剤としてのピリジン−3−イル酢酸誘導体 |
| EP3565810A1 (en) | 2017-01-03 | 2019-11-13 | ViiV Healthcare UK (No.5) Limited | Pyridin-3-yl acetic acid derivatives as inhibitors of human immunodeficiency virus replication |
| TWI714820B (zh) | 2017-01-31 | 2021-01-01 | 美商基利科學股份有限公司 | 替諾福韋艾拉酚胺(tenofovir alafenamide)之晶型 |
| JOP20180009A1 (ar) | 2017-02-06 | 2019-01-30 | Gilead Sciences Inc | مركبات مثبط فيروس hiv |
| WO2018237148A1 (en) | 2017-06-21 | 2018-12-27 | Gilead Sciences, Inc. | Multispecific antibodies that target hiv gp120 and cd3 |
| RU2755710C2 (ru) | 2017-06-30 | 2021-09-20 | Вайв Хелткер Компани | Комбинация, ее применение и способы лечения с использованием указанной комбинации |
| EP3661937B1 (en) | 2017-08-01 | 2021-07-28 | Gilead Sciences, Inc. | Crystalline forms of ethyl ((s)-((((2r,5r)-5-(6-amino-9h-purin-9-yl)-4-fluoro-2,5-dihydrofuran-2-yl)oxy)methyl)(phenoxy)phosphoryl)-l-alaninate (gs-9131) for treating viral infections |
| AR112413A1 (es) | 2017-08-17 | 2019-10-23 | Gilead Sciences Inc | Formas sólidas de un inhibidor de la cápside del vih |
| AR112412A1 (es) | 2017-08-17 | 2019-10-23 | Gilead Sciences Inc | Formas de sal de colina de un inhibidor de la cápside del vih |
| AU2018319538B9 (en) | 2017-08-22 | 2021-05-27 | Gilead Sciences, Inc. | Therapeutic heterocyclic compounds |
| JOP20180092A1 (ar) | 2017-10-13 | 2019-04-13 | Gilead Sciences Inc | مثبطات hiv بروتياز |
| EP3700573A1 (en) | 2017-10-24 | 2020-09-02 | Gilead Sciences, Inc. | Methods of treating patients co-infected with a virus and tuberculosis |
| LT3706762T (lt) | 2017-12-07 | 2024-12-27 | Emory University | N4-hidroksicitidinas ir jo dariniai bei susiję naudojimo prieš virusus būdai |
| EP3728282B1 (en) | 2017-12-20 | 2023-11-22 | Institute of Organic Chemistry and Biochemistry ASCR, V.V.I. | 2'3' cyclic dinucleotides with phosphonate bond activating the sting adaptor protein |
| CN111566120B (zh) | 2017-12-20 | 2023-09-29 | 捷克共和国有机化学与生物化学研究所 | 活化sting转接蛋白的具有膦酸酯键的3’3’环状二核苷酸 |
| WO2019144015A1 (en) | 2018-01-19 | 2019-07-25 | Gilead Sciences, Inc. | Metabolites of bictegravir |
| KR102587510B1 (ko) | 2018-02-15 | 2023-10-11 | 길리애드 사이언시즈, 인코포레이티드 | 피리딘 유도체 및 hiv 감염을 치료하기 위한 그의 용도 |
| CA3281991A1 (en) | 2018-02-16 | 2025-11-29 | Gilead Sciences, Inc. | Methods and intermediates for preparing therapeutic compounds useful in the treatment of retroviridae viral infection |
| TWI833744B (zh) | 2018-04-06 | 2024-03-01 | 捷克科學院有機化學與生物化學研究所 | 3'3'-環二核苷酸 |
| TWI818007B (zh) | 2018-04-06 | 2023-10-11 | 捷克科學院有機化學與生物化學研究所 | 2'3'-環二核苷酸 |
| TW202005654A (zh) | 2018-04-06 | 2020-02-01 | 捷克科學院有機化學與生物化學研究所 | 2,2,─環二核苷酸 |
| WO2019211799A1 (en) | 2018-05-03 | 2019-11-07 | Institute Of Organic Chemistry And Biochemistry Ascr, V.V.I. | 2'3'-cyclic dinucleotide analogue comprising a cyclopentanyl modified nucleotide |
| SG11202012043RA (en) | 2018-07-03 | 2021-01-28 | Gilead Sciences Inc | Antibodies that target hiv gp120 and methods of use |
| KR102651420B1 (ko) | 2018-07-06 | 2024-03-28 | 길리애드 사이언시즈, 인코포레이티드 | 치료 헤테로시클릭 화합물 |
| CN112384283B (zh) | 2018-07-06 | 2023-08-15 | 吉利德科学公司 | 治疗性的杂环化合物 |
| JP2021530523A (ja) | 2018-07-16 | 2021-11-11 | ギリアード サイエンシーズ, インコーポレイテッド | Hivの処置のためのカプシド阻害剤 |
| TWI766172B (zh) | 2018-07-30 | 2022-06-01 | 美商基利科學股份有限公司 | 抗hiv化合物 |
| CN112996517A (zh) | 2018-09-19 | 2021-06-18 | 吉利德科学公司 | 预防hiv的整合酶抑制剂 |
| US11179397B2 (en) | 2018-10-03 | 2021-11-23 | Gilead Sciences, Inc. | Imidazopyrimidine derivatives |
| CN117105933A (zh) | 2018-10-31 | 2023-11-24 | 吉利德科学公司 | 具有hpk1抑制活性的取代的6-氮杂苯并咪唑化合物 |
| CN113227089B (zh) | 2018-10-31 | 2024-07-05 | 吉利德科学公司 | 作为hpk1抑制剂的取代的6-氮杂苯并咪唑化合物 |
| WO2020176505A1 (en) | 2019-02-25 | 2020-09-03 | Gilead Sciences, Inc. | Protein kinase c agonists |
| WO2020176510A1 (en) | 2019-02-25 | 2020-09-03 | Gilead Sciences, Inc. | Protein kinase c agonists |
| EP3935065A1 (en) | 2019-03-07 | 2022-01-12 | Institute of Organic Chemistry and Biochemistry ASCR, V.V.I. | 3'3'-cyclic dinucleotide analogue comprising a cyclopentanyl modified nucleotide as sting modulator |
| EP3934757B1 (en) | 2019-03-07 | 2023-02-22 | Institute of Organic Chemistry and Biochemistry ASCR, V.V.I. | 2'3'-cyclic dinucleotides and prodrugs thereof |
| US20220143061A1 (en) | 2019-03-07 | 2022-05-12 | Institute Of Organic Chemistry And Biochemistry Ascr, V.V.I. | 3'3'-cyclic dinucleotides and prodrugs thereof |
| SI3938047T1 (sl) | 2019-03-22 | 2022-10-28 | Gilead Sciences, Inc. | Premoščene triciklične karbamoilpiridonske spojine in njihova farmacevtska uporaba |
| TWI751516B (zh) | 2019-04-17 | 2022-01-01 | 美商基利科學股份有限公司 | 類鐸受體調節劑之固體形式 |
| WO2020214647A1 (en) | 2019-04-17 | 2020-10-22 | Gilead Sciences, Inc. | Solid forms of an hiv protease inhibitor |
| TW202104210A (zh) | 2019-04-17 | 2021-02-01 | 美商基利科學股份有限公司 | Hiv蛋白酶抑制劑 |
| TWI751517B (zh) | 2019-04-17 | 2022-01-01 | 美商基利科學股份有限公司 | 類鐸受體調節劑之固體形式 |
| TW202231277A (zh) | 2019-05-21 | 2022-08-16 | 美商基利科學股份有限公司 | 鑑別對使用gp120 v3聚醣導向之抗體的治療敏感之hiv病患的方法 |
| EP3972695A1 (en) | 2019-05-23 | 2022-03-30 | Gilead Sciences, Inc. | Substituted exo-methylene-oxindoles which are hpk1/map4k1 inhibitors |
| RU2717101C1 (ru) | 2019-06-03 | 2020-03-18 | Андрей Александрович Иващенко | Анелированные 9-гидрокси-1,8-диоксо-1,3,4,8-тетрагидро-2Н-пиридо[1,2-a]пиразин-7-карбоксамиды - ингибиторы интегразы ВИЧ, способы их получения и применения |
| CA3140708A1 (en) | 2019-06-18 | 2020-12-24 | Helen Horton | Combination of hepatitis b virus (hbv) vaccines and pyridopyrimidine derivatives |
| JP7295283B2 (ja) | 2019-06-25 | 2023-06-20 | ギリアード サイエンシーズ, インコーポレイテッド | Flt3l-fc融合タンパク質及び使用方法 |
| JP7454645B2 (ja) | 2019-07-16 | 2024-03-22 | ギリアード サイエンシーズ, インコーポレイテッド | Hivワクチン並びにその作製方法及び使用方法 |
| WO2021011891A1 (en) | 2019-07-18 | 2021-01-21 | Gilead Sciences, Inc. | Long-acting formulations of tenofovir alafenamide |
| EP4017476A1 (en) | 2019-08-19 | 2022-06-29 | Gilead Sciences, Inc. | Pharmaceutical formulations of tenofovir alafenamide |
| EP4643882A2 (en) | 2019-11-26 | 2025-11-05 | Gilead Sciences, Inc. | Capsid inhibitors for the prevention of hiv |
| CN117736207A (zh) | 2019-12-24 | 2024-03-22 | 卡尔那生物科学株式会社 | 二酰基甘油激酶调节化合物 |
| WO2021173522A1 (en) | 2020-02-24 | 2021-09-02 | Gilead Sciences, Inc. | Tetracyclic compounds for treating hiv infection |
| TWI845826B (zh) | 2020-03-20 | 2024-06-21 | 美商基利科學股份有限公司 | 4'-c-經取代-2-鹵基-2'-去氧腺苷核苷之前藥及其製造與使用方法 |
| EP4153181A1 (en) | 2020-05-21 | 2023-03-29 | Gilead Sciences, Inc. | Pharmaceutical compositions comprising bictegravir |
| CA3181690A1 (en) | 2020-06-25 | 2021-12-30 | Chienhung CHOU | Capsid inhibitors for the treatment of hiv |
| MX2023001507A (es) | 2020-08-07 | 2023-03-06 | Gilead Sciences Inc | Profarmacos de analogos de nucleotidos de fosfonamida y su uso farmaceutico. |
| KR20230079137A (ko) | 2020-09-30 | 2023-06-05 | 길리애드 사이언시즈, 인코포레이티드 | 가교된 트리사이클릭 카르바모일피리돈 화합물 및 이의 용도 |
| TWI815194B (zh) | 2020-10-22 | 2023-09-11 | 美商基利科學股份有限公司 | 介白素2-Fc融合蛋白及使用方法 |
| US20220144923A1 (en) | 2020-11-11 | 2022-05-12 | Gilead Sciences, Inc. | METHODS OF IDENTIFYING HIV PATIENTS SENSITIVE TO THERAPY WITH gp120 CD4 BINDING SITE-DIRECTED ANTIBODIES |
| PT4196479T (pt) | 2021-01-19 | 2024-01-03 | Gilead Sciences Inc | Compostos de piridotriazinas substituídos e suas utilizações |
| WO2022245671A1 (en) | 2021-05-18 | 2022-11-24 | Gilead Sciences, Inc. | Methods of using flt3l-fc fusion proteins |
| CN117377671A (zh) | 2021-06-23 | 2024-01-09 | 吉利德科学公司 | 二酰基甘油激酶调节化合物 |
| JP7686091B2 (ja) | 2021-06-23 | 2025-05-30 | ギリアード サイエンシーズ, インコーポレイテッド | ジアシルグリセロールキナーゼ調節化合物 |
| CN117480155A (zh) | 2021-06-23 | 2024-01-30 | 吉利德科学公司 | 二酰基甘油激酶调节化合物 |
| EP4359415A1 (en) | 2021-06-23 | 2024-05-01 | Gilead Sciences, Inc. | Diacylglyercol kinase modulating compounds |
| WO2023102523A1 (en) | 2021-12-03 | 2023-06-08 | Gilead Sciences, Inc. | Therapeutic compounds for hiv virus infection |
| CN118355020A (zh) | 2021-12-03 | 2024-07-16 | 吉利德科学公司 | Hiv病毒感染的治疗性化合物 |
| FI4445900T3 (fi) | 2021-12-03 | 2025-08-05 | Gilead Sciences Inc | Terapeuttisia yhdisteitä hiv-virusinfektiota varten |
| TWI856796B (zh) | 2022-04-06 | 2024-09-21 | 美商基利科學股份有限公司 | 橋聯三環胺甲醯基吡啶酮化合物及其用途 |
| EP4547659A1 (en) | 2022-07-01 | 2025-05-07 | Gilead Sciences, Inc. | Therapeutic compounds useful for the prophylactic or therapeutic treatment of an hiv virus infection |
| EP4554628A1 (en) | 2022-07-12 | 2025-05-21 | Gilead Sciences, Inc. | Hiv immunogenic polypeptides and vaccines and uses thereof |
| CA3265134A1 (en) | 2022-08-26 | 2024-02-29 | Gilead Sciences, Inc. | DOSING AND PLANNING REGIMEN FOR BROADLY NEUTRALIZING ANTIBODIES |
| WO2024076915A1 (en) | 2022-10-04 | 2024-04-11 | Gilead Sciences, Inc. | 4'-thionucleoside analogues and their pharmaceutical use |
| AU2024259111A1 (en) | 2023-04-19 | 2025-10-16 | Gilead Sciences, Inc. | Dosing regimen of capsid inhibitor |
| US20250011352A1 (en) | 2023-05-31 | 2025-01-09 | Gilead Sciences, Inc. | Solid forms |
| WO2024249517A1 (en) | 2023-05-31 | 2024-12-05 | Gilead Sciences, Inc. | Anti-hiv compounds |
| US20250042926A1 (en) | 2023-05-31 | 2025-02-06 | Gilead Sciences, Inc. | Therapeutic compounds for hiv |
| WO2025029247A1 (en) | 2023-07-28 | 2025-02-06 | Gilead Sciences, Inc. | Weekly regimen of lenacapavir for the treatment and prevention of hiv |
| WO2025042394A1 (en) | 2023-08-23 | 2025-02-27 | Gilead Sciences, Inc. | Dosing regimen of hiv capsid inhibitor |
| WO2025076542A1 (en) | 2023-10-05 | 2025-04-10 | Jones R Brad | Atovaquone as an ros inducer for use in the elimination of hiv-infected t-cells |
| WO2025080863A1 (en) | 2023-10-11 | 2025-04-17 | Gilead Sciences, Inc. | Bridged tricyclic carbamoylpyridone compounds and uses thereof |
| US20250127801A1 (en) | 2023-10-11 | 2025-04-24 | Gilead Sciences, Inc. | Bridged tricyclic carbamoylpyridone compounds and uses thereof |
| US20250120989A1 (en) | 2023-10-11 | 2025-04-17 | Gilead Sciences, Inc. | Bridged tricyclic carbamoylpyridone compounds and uses thereof |
| WO2025137245A1 (en) | 2023-12-22 | 2025-06-26 | Gilead Sciences, Inc. | Solid forms of hiv integrase inhibitors |
| WO2025184447A1 (en) | 2024-03-01 | 2025-09-04 | Gilead Sciences, Inc. | Pharmaceutical compositions comprising hiv integrase inhibitors |
| WO2025184452A1 (en) | 2024-03-01 | 2025-09-04 | Gilead Sciences, Inc. | Solid forms of hiv integrase inhibitors |
| WO2025184609A1 (en) | 2024-03-01 | 2025-09-04 | Gilead Sciences, Inc. | Antiviral compounds |
| US20250326779A1 (en) | 2024-04-03 | 2025-10-23 | Gilead Sciences, Inc. | Anti-hiv compounds |
| WO2025260028A1 (en) | 2024-06-14 | 2025-12-18 | Gilead Sciences, Inc. | Pharmaceutical compositions comprising hiv integrase inhibitors |
Family Cites Families (89)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3895028A (en) * | 1972-09-12 | 1975-07-15 | Tokyo Tanabe Co | Alpha-(2-phenylbenzothiazol-5-yl)propionic acid |
| JPS4994667A (enExample) | 1973-01-23 | 1974-09-09 | ||
| FR2453163A1 (fr) | 1979-04-03 | 1980-10-31 | Rolland Sa A | Derives de benzothiazole, leur procede de preparation et leurs applications en therapeutique |
| US4816570A (en) | 1982-11-30 | 1989-03-28 | The Board Of Regents Of The University Of Texas System | Biologically reversible phosphate and phosphonate protective groups |
| GB8403739D0 (en) * | 1984-02-13 | 1984-03-14 | Roussel Lab Ltd | Chemical compounds |
| US4968788A (en) | 1986-04-04 | 1990-11-06 | Board Of Regents, The University Of Texas System | Biologically reversible phosphate and phosphonate protective gruops |
| JP3347723B2 (ja) | 1990-06-13 | 2002-11-20 | グラツィエル,アーノルド | 含リンプロドラッグ |
| EP0481214B1 (en) | 1990-09-14 | 1998-06-24 | Institute Of Organic Chemistry And Biochemistry Of The Academy Of Sciences Of The Czech Republic | Prodrugs of phosphonates |
| US5733906A (en) | 1993-10-12 | 1998-03-31 | Eli Lilly And Company | Inhibitors of HIV Protease useful for the treatment of Aids |
| MX9308016A (es) | 1992-12-22 | 1994-08-31 | Lilly Co Eli | Compuestos inhibidores de la proteasa del virus de la inmunodeficiencia humana, procedimiento para su preparacion y formulacion farmaceutica que los contiene. |
| EP0693126B9 (en) | 1993-04-02 | 2007-09-12 | Rigel Pharmaceuticals, Inc. | Method for selective inactivation of viral replication |
| JP3287558B2 (ja) | 1993-07-27 | 2002-06-04 | 株式会社半導体エネルギー研究所 | 半導体装置の作製方法 |
| US5434188A (en) | 1994-03-07 | 1995-07-18 | Warner-Lambert Company | 1-ether and 1-thioether-naphthalene-2-carboxamides as inhibitors of cell adhesion and as inhibitors of the activation of HIV |
| DE4428932A1 (de) | 1994-08-16 | 1996-02-22 | Hoechst Ag | Substituierte-Chinolinderivate, Verfahren zu ihrer Herstellung und ihre Verwendung |
| CA2327929A1 (en) | 1998-04-09 | 1999-10-21 | Merck & Co., Inc. | Oxidation process using periodic acid |
| WO2000063152A1 (en) | 1999-02-22 | 2000-10-26 | The Government Of The United States Of America As Represented By The Secretary, Department Of Health And Human Services | Acetylated and related analogues of chicoric acid as hiv integrase inhibitors |
| US20020052323A1 (en) | 2000-08-30 | 2002-05-02 | Jinhai Wang | Quinoline-(C=O)-(multiple amino acids)-leaving group compounds for pharmaceutical compositions and reagents |
| DE60137356D1 (de) | 2000-11-21 | 2009-02-26 | Sunesis Pharmaceuticals Inc | Erweiterter "tethering" ansatz zum schnellen auffinden von liganden |
| FR2819507B1 (fr) | 2001-01-17 | 2007-09-28 | Inst Rech Developpement Ird | Quinoleines substituees pour le traitement de co-infections a protozoaires et a retrovirus |
| FR2839646B1 (fr) | 2002-05-17 | 2008-04-11 | Bioalliance Pharma | Utilisation de derives de quinoleine a effet anti-integrase et ses applications |
| EP1545518A1 (en) | 2002-08-02 | 2005-06-29 | Tibotec Pharmaceuticals Ltd. | Broadspectrum 2-amino-benzothiazole sulfonamide hiv protease inhibitors |
| KR101327772B1 (ko) * | 2002-08-02 | 2013-11-11 | 얀센 알 앤드 디 아일랜드 | 광범위 2-아미노-벤조티아졸 설폰아미드 hiv 프로테아제 저해제 |
| EP2045242A1 (en) | 2002-08-13 | 2009-04-08 | Shionogi&Co., Ltd. | Heterocyclic compounds having inhibitory activity against HIV integrase |
| US7514233B2 (en) | 2002-09-26 | 2009-04-07 | K.U. Leuven Research & Development | Integrase cofactor |
| SI1564210T1 (sl) | 2002-11-20 | 2010-01-29 | Japan Tobacco Inc | 4-oksokinolinske spojine in njihova uporaba kot inhibitorji HIV integraze |
| UA80571C2 (en) | 2002-11-22 | 2007-10-10 | Lilly Co Eli | Quinolinyl-pyrrolopyrazoles |
| EP2258365B1 (en) | 2003-03-28 | 2013-05-29 | Novartis Vaccines and Diagnostics, Inc. | Use of organic compounds for immunopotentiation |
| JP2008502719A (ja) | 2004-05-21 | 2008-01-31 | メルク エンド カムパニー インコーポレーテッド | アミノシクロペンチル複素環および炭素環系ケモカイン受容体活性調節剤 |
| US7087610B2 (en) * | 2004-06-03 | 2006-08-08 | Bristol-Myers Squibb Company | Benzothiazole antiviral agents |
| KR20070026841A (ko) | 2004-06-22 | 2007-03-08 | 스미스클라인 비참 코포레이션 | 화합물 |
| TWI306401B (en) | 2004-08-13 | 2009-02-21 | Nat Health Research Institutes | Benzothiazolium compounds |
| US20060094755A1 (en) | 2004-10-28 | 2006-05-04 | Bioflexis, Llc | Novel quinoline-based metal chelators as antiviral agents |
| TWI370820B (en) | 2005-04-27 | 2012-08-21 | Takeda Pharmaceutical | Fused heterocyclic compounds |
| WO2006124780A2 (en) | 2005-05-12 | 2006-11-23 | Kalypsys, Inc. | Ih-benzo [d] imidazole compounds as inhibitors of b-raf kinase |
| US7473784B2 (en) * | 2005-08-01 | 2009-01-06 | Bristol-Myers Squibb Company | Benzothiazole and azabenzothiazole compounds useful as kinase inhibitors |
| US7939545B2 (en) * | 2006-05-16 | 2011-05-10 | Boehringer Ingelheim International Gmbh | Inhibitors of human immunodeficiency virus replication |
| CA2651979A1 (en) | 2006-05-30 | 2007-12-06 | Pfizer Products Inc. | Triazolopyridazine derivatives |
| JO2841B1 (en) * | 2006-06-23 | 2014-09-15 | تيبوتيك فارماسيوتيكالز ليمتد | 2-(substituted-amino) -benzothiazole sulfonamide as protease inhibitors HIV (HIV) |
| US8435774B2 (en) | 2006-06-28 | 2013-05-07 | Qiagen Gmbh | Enhancing reactivation of thermostable reversibly inactivated enzymes |
| WO2008053478A2 (en) | 2006-10-30 | 2008-05-08 | Yissum Research Development Company Of The Hebrew University Of Jerusalem | Compositions and methods for inhibiting hiv-1 replication and integrase activity |
| RU2469032C2 (ru) | 2006-12-13 | 2012-12-10 | Ф.Хоффманн-Ля Рош Аг | Производные 2-(пиперидин-4-ил)-4-фенокси- или фениламинопиримидина в качестве ненуклеозидных ингибиторов обратной транскриптазы |
| RU2503679C2 (ru) * | 2007-11-15 | 2014-01-10 | Джилид Сайенсиз, Инк. | Ингибиторы репликации вируса иммунодефицита человека |
| SI2220076T1 (sl) | 2007-11-15 | 2012-05-31 | Gilead Sciences Inc | Inhibitorji replikacije virusa humane imunske pomankljivosti |
| WO2009062308A1 (en) | 2007-11-16 | 2009-05-22 | Boehringer Ingelheim International Gmbh | Inhibitors of human immunodeficiency virus replication |
| KR20100097156A (ko) | 2007-11-16 | 2010-09-02 | 베링거 인겔하임 인터내셔날 게엠베하 | 사람 면역결핍 바이러스 복제의 억제제 |
| GB0801940D0 (en) | 2008-02-01 | 2008-03-12 | Univ Leuven Kath | Inhibitors of lentiviral replication |
| JP2011511005A (ja) | 2008-02-04 | 2011-04-07 | オーエスアイ・フアーマスーテイカルズ・インコーポレーテツド | 2−アミノピリジン系キナーゼ阻害薬 |
| ES2548141T3 (es) | 2008-11-20 | 2015-10-14 | Glaxosmithkline Llc | Compuestos químicos |
| US8338441B2 (en) | 2009-05-15 | 2012-12-25 | Gilead Sciences, Inc. | Inhibitors of human immunodeficiency virus replication |
| GB0908394D0 (en) | 2009-05-15 | 2009-06-24 | Univ Leuven Kath | Novel viral replication inhibitors |
| WO2011002635A1 (en) | 2009-06-30 | 2011-01-06 | Siga Technologies, Inc. | Treatment and prevention of dengue virus infections |
| GB0913636D0 (en) | 2009-08-05 | 2009-09-16 | Univ Leuven Kath | Novel viral replication inhibitors |
| WO2011047129A1 (en) | 2009-10-15 | 2011-04-21 | Southern Research Institute | Treatment of neurodegenerative diseases, causation of memory enhancement, and assay for screening compounds for such |
| CN102770181B (zh) | 2009-12-23 | 2015-08-12 | 勒芬天主教大学 | 抗病毒化合物 |
| US20110223131A1 (en) | 2010-02-24 | 2011-09-15 | Gilead Sciences, Inc. | Antiviral compounds |
| CA2800176C (en) | 2010-05-24 | 2018-08-28 | University Of Rochester | Bicyclic heteroaryl kinase inhibitors and methods of use |
| SG186820A1 (en) | 2010-07-02 | 2013-02-28 | Gilead Sciences Inc | Napht- 2 -ylacetic acid derivatives to treat aids |
| BR112012033689A2 (pt) | 2010-07-02 | 2019-09-24 | Gilead Sciences Inc | derivados de ácido 2-quinolinil-acético como compostos de hiv antivirais |
| US8633200B2 (en) | 2010-09-08 | 2014-01-21 | Bristol-Myers Squibb Company | Inhibitors of human immunodeficiency virus replication |
| BR112013011737A2 (pt) | 2010-11-15 | 2016-08-09 | Univ Leuven Kath | composto, uso de um composto composição farmacêutica, e, método de tratamento ou prevenção de uma infecção por hiv |
| CA2817896A1 (en) | 2010-11-15 | 2012-05-24 | Viiv Healthcare Uk Limited | Inhibitors of hiv replication |
| TWI538905B (zh) | 2010-12-22 | 2016-06-21 | H 朗德貝克公司 | 雙環[3.2.1]辛基醯胺衍生物及其用途 |
| US9029391B2 (en) | 2011-01-24 | 2015-05-12 | Viiv Healthcare Uk Limited | Isoquinoline compounds and methods for treating HIV |
| AU2012240314A1 (en) | 2011-04-04 | 2013-05-02 | Gilead Sciences, Inc. | Process for the preparation of an HIV integrase inhibitor |
| TW201302761A (zh) | 2011-04-04 | 2013-01-16 | Gilead Sciences Inc | Hiv抑制劑之固態形式 |
| EP2508511A1 (en) | 2011-04-07 | 2012-10-10 | Laboratoire Biodim | Inhibitors of viral replication, their process of preparation and their therapeutical uses |
| EP2511273B8 (en) | 2011-04-15 | 2019-06-26 | Hivih | Inhibitors of viral replication, their process of preparation and their therapeutical uses |
| DK2699575T3 (da) | 2011-04-21 | 2015-06-22 | Bayer Ip Gmbh | Triazolopyridiner |
| ES2615734T3 (es) | 2011-04-21 | 2017-06-08 | Gilead Sciences, Inc. | Compuestos de benzotiazol y su uso farmacéutico |
| WO2012143143A1 (en) | 2011-04-21 | 2012-10-26 | Origenis Gmbh | Heterocyclic compounds as kinase inhibitors |
| WO2012143144A1 (en) | 2011-04-21 | 2012-10-26 | Origenis Gmbh | Pyrazolo [4, 3-d] pyrimidines useful as kinase inhibitors |
| WO2013002357A1 (ja) | 2011-06-30 | 2013-01-03 | 塩野義製薬株式会社 | Hiv複製阻害剤 |
| US8791108B2 (en) | 2011-08-18 | 2014-07-29 | Bristol-Myers Squibb Company | Inhibitors of human immunodeficiency virus replication |
| ES2632443T3 (es) | 2011-09-22 | 2017-09-13 | Viiv Healthcare Uk Limited | Compuestos de pirrolopiridinona y procedimientos de tratamiento del VIH |
| WO2013058448A1 (ko) | 2011-10-20 | 2013-04-25 | 한국해양연구원 | 내분비계 장애물질 노출에 대응하는 바다송사리 유전자 및 이를 이용한 수생태계 환경오염 진단 방법 |
| JP6099149B2 (ja) | 2011-10-25 | 2017-03-22 | 塩野義製薬株式会社 | Hiv複製阻害剤 |
| US8332160B1 (en) * | 2011-11-17 | 2012-12-11 | Amyris Biotechnologies, Inc. | Systems and methods for engineering nucleic acid constructs using scoring techniques |
| US9284323B2 (en) | 2012-01-04 | 2016-03-15 | Gilead Sciences, Inc. | Naphthalene acetic acid derivatives against HIV infection |
| US9376392B2 (en) | 2012-01-04 | 2016-06-28 | Gilead Sciences, Inc. | 2-(tert-butoxy)-2-(7-methylquinolin-6-yl) acetic acid derivatives for treating AIDS |
| HK1208875A1 (en) | 2012-01-12 | 2016-03-18 | 耶鲁大学 | Compounds & methods for the enhanced degradation of targeted proteins & other polypeptides by an e3 ubiquitin ligase |
| US8629276B2 (en) | 2012-02-15 | 2014-01-14 | Bristol-Myers Squibb Company | Inhibitors of human immunodeficiency virus replication |
| US9034882B2 (en) | 2012-03-05 | 2015-05-19 | Bristol-Myers Squibb Company | Inhibitors of human immunodeficiency virus replication |
| US9006235B2 (en) | 2012-03-06 | 2015-04-14 | Bristol-Myers Squibb Company | Inhibitors of human immunodeficiency virus replication |
| WO2013157622A1 (ja) | 2012-04-19 | 2013-10-24 | 塩野義製薬株式会社 | Hiv複製阻害剤 |
| MX2014005002A (es) | 2012-04-20 | 2014-07-09 | Gilead Sciences Inc | Derivados de acido benzotiazol-6-il acetico y su uso para tratar una infeccion por vih. |
| EP2877468B1 (en) | 2012-07-12 | 2017-08-23 | ViiV Healthcare UK Limited | Compounds and methods for treating hiv |
| US8906929B2 (en) | 2012-08-16 | 2014-12-09 | Bristol-Myers Squibb Company | Inhibitors of human immunodeficiency virus replication |
| US20140094609A1 (en) | 2012-10-03 | 2014-04-03 | Gilead Sciences, Inc. | Process for the preparation of an hiv integrase inhibitor |
| US20140094485A1 (en) | 2012-10-03 | 2014-04-03 | Gilead Sciences, Inc. | Solid state forms of hiv inhibitor |
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