ES2567197T3 - Derivado de carbamoilpiridona policíclico que tiene actividad inhibidora de la integrasa del VIH - Google Patents
Derivado de carbamoilpiridona policíclico que tiene actividad inhibidora de la integrasa del VIH Download PDFInfo
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- ES2567197T3 ES2567197T3 ES12159079.8T ES12159079T ES2567197T3 ES 2567197 T3 ES2567197 T3 ES 2567197T3 ES 12159079 T ES12159079 T ES 12159079T ES 2567197 T3 ES2567197 T3 ES 2567197T3
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- -1 Polycyclic carbamoylpyridone derivative Chemical class 0.000 title description 9
- 230000002401 inhibitory effect Effects 0.000 title description 5
- 108010002459 HIV Integrase Proteins 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 45
- 150000003839 salts Chemical class 0.000 claims abstract description 21
- 239000012453 solvate Substances 0.000 claims abstract description 7
- 239000000203 mixture Substances 0.000 claims description 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 239000003814 drug Substances 0.000 claims description 10
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 9
- 239000002259 anti human immunodeficiency virus agent Substances 0.000 claims description 8
- 229940124411 anti-hiv antiviral agent Drugs 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- 159000000000 sodium salts Chemical group 0.000 claims description 7
- 239000000137 peptide hydrolase inhibitor Substances 0.000 claims description 6
- 239000003419 rna directed dna polymerase inhibitor Substances 0.000 claims description 6
- 208000031886 HIV Infections Diseases 0.000 claims description 5
- 238000011282 treatment Methods 0.000 claims description 5
- 208000037357 HIV infectious disease Diseases 0.000 claims description 4
- 229940042399 direct acting antivirals protease inhibitors Drugs 0.000 claims description 4
- 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 claims description 4
- 238000011321 prophylaxis Methods 0.000 claims description 4
- 229940124597 therapeutic agent Drugs 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 238000013160 medical therapy Methods 0.000 claims description 2
- TUBHMQLHDDHKCJ-CJNGLKHVSA-N (4as,13ar)-n-[(2,4-difluorophenyl)methyl]-10-hydroxy-9,11-dioxo-2,3,4a,5,9,11,13,13a-octahydro-1h-pyrido[1,2-a]pyrrolo[1',2': 3,4]imidazo[1,2-d]pyrazine-8-carboxamide Chemical group C([C@H]1N2CCC[C@@H]2CN1C(=O)C1=C(C2=O)O)N1C=C2C(=O)NCC1=CC=C(F)C=C1F TUBHMQLHDDHKCJ-CJNGLKHVSA-N 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 33
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 32
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 32
- 239000007864 aqueous solution Substances 0.000 description 24
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- 239000013078 crystal Substances 0.000 description 19
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- 230000002829 reductive effect Effects 0.000 description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 16
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 16
- 239000002904 solvent Substances 0.000 description 16
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- 239000002253 acid Substances 0.000 description 14
- 239000003795 chemical substances by application Substances 0.000 description 13
- 229920006395 saturated elastomer Polymers 0.000 description 13
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 12
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 238000001816 cooling Methods 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
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- 229960004132 diethyl ether Drugs 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 210000004027 cell Anatomy 0.000 description 7
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- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 235000019270 ammonium chloride Nutrition 0.000 description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 6
- 230000010534 mechanism of action Effects 0.000 description 6
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- 150000004702 methyl esters Chemical class 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- IIFVWLUQBAIPMJ-UHFFFAOYSA-N (4-fluorophenyl)methanamine Chemical compound NCC1=CC=C(F)C=C1 IIFVWLUQBAIPMJ-UHFFFAOYSA-N 0.000 description 4
- FNJFXPQAVMEMIC-UHFFFAOYSA-N O1C=CN2C1=CN1C(=C2)C=CC(=C1)C(=O)N Chemical compound O1C=CN2C1=CN1C(=C2)C=CC(=C1)C(=O)N FNJFXPQAVMEMIC-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- OHEKQGOBJIKKIF-AWEZNQCLSA-N (12as)-n-[(4-fluorophenyl)methyl]-7-hydroxy-6,8-dioxo-3,4,12,12a-tetrahydro-2h-pyrido[5,6]pyrazino[2,6-b][1,3]oxazine-9-carboxamide Chemical compound C([C@@H]1OCCCN1C(=O)C1=C(C2=O)O)N1C=C2C(=O)NCC1=CC=C(F)C=C1 OHEKQGOBJIKKIF-AWEZNQCLSA-N 0.000 description 3
- 241000713800 Feline immunodeficiency virus Species 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 241000713311 Simian immunodeficiency virus Species 0.000 description 3
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 230000036436 anti-hiv Effects 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000006196 drop Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 208000015181 infectious disease Diseases 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 239000002850 integrase inhibitor Substances 0.000 description 3
- 229940124524 integrase inhibitor Drugs 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000010898 silica gel chromatography Methods 0.000 description 3
- 238000002560 therapeutic procedure Methods 0.000 description 3
- WHHKTPDAWDQDKG-UHFFFAOYSA-N 1,8,11-triazatetracyclo[8.6.0.03,8.011,15]hexadeca-2,4,6,9,13,15-hexaene-6-carboxamide Chemical compound C1=C2N3CC=CC3=CN2C=C2C=CC(C(=O)N)=CN21 WHHKTPDAWDQDKG-UHFFFAOYSA-N 0.000 description 2
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 2
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 2
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 description 2
- 229940099797 HIV integrase inhibitor Drugs 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 102100034343 Integrase Human genes 0.000 description 2
- 108010061833 Integrases Proteins 0.000 description 2
- 108060001084 Luciferase Proteins 0.000 description 2
- 239000005089 Luciferase Substances 0.000 description 2
- 229940124158 Protease/peptidase inhibitor Drugs 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 239000003443 antiviral agent Substances 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 238000002648 combination therapy Methods 0.000 description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical class OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 239000003084 hiv integrase inhibitor Substances 0.000 description 2
- 229910017053 inorganic salt Inorganic materials 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
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- 229910052708 sodium Inorganic materials 0.000 description 2
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- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
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- GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 description 1
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- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 1
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- AUKXFNABVHIUAC-RXMQYKEDSA-N (R)-pyrrolidin-2-ylmethylamine Chemical compound NC[C@H]1CCCN1 AUKXFNABVHIUAC-RXMQYKEDSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- LVEYOSJUKRVCCF-UHFFFAOYSA-N 1,3-bis(diphenylphosphino)propane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCP(C=1C=CC=CC=1)C1=CC=CC=C1 LVEYOSJUKRVCCF-UHFFFAOYSA-N 0.000 description 1
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- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical class CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
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- JRLTTZUODKEYDH-UHFFFAOYSA-N 8-methylquinoline Chemical group C1=CN=C2C(C)=CC=CC2=C1 JRLTTZUODKEYDH-UHFFFAOYSA-N 0.000 description 1
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- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
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- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/4985—Pyrazines or piperazines ortho- or peri-condensed with heterocyclic ring systems
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- A61K31/551—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having two nitrogen atoms, e.g. dilazep
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- 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
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- 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
- C07D471/12—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 three hetero rings
- C07D471/14—Ortho-condensed systems
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- 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
- C07D471/22—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 systems contains four or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D498/20—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/22—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains four or more hetero rings
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Families Citing this family (152)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101723949B (zh) | 2003-12-24 | 2013-10-23 | 生物区科学管理控股有限公司 | 用于治疗呼吸道合胞体病毒感染的多环试剂 |
| US7273859B2 (en) * | 2004-05-12 | 2007-09-25 | Bristol-Myers Squibb Company | HIV integrase inhibitors: cyclic pyrimidinone compounds |
| ES2567197T3 (es) * | 2005-04-28 | 2016-04-20 | Viiv Healthcare Company | Derivado de carbamoilpiridona policíclico que tiene actividad inhibidora de la integrasa del VIH |
| WO2006121831A2 (en) | 2005-05-10 | 2006-11-16 | Merck & Co., Inc. | Hiv integrase inhibitors |
| JP5094725B2 (ja) | 2005-10-04 | 2012-12-12 | イステイチユート・デイ・リチエルケ・デイ・ビオロジア・モレコラーレ・ピ・アンジエレツテイ・エツセ・エルレ・エルレ | Ｈｉｖインテグラーゼ阻害剤 |
| KR20080064182A (ko) * | 2005-10-27 | 2008-07-08 | 시오노기세야쿠 가부시키가이샤 | Ｈｉｖ 인테그라아제 억제활성을 가지는 다환성카르바모일피리돈 유도체 |
| TWI423972B (zh) | 2006-09-28 | 2014-01-21 | Biota Scient Management | 治療呼吸系融合細胞病毒感染之多環劑 |
| CN102124011A (zh) | 2007-11-15 | 2011-07-13 | 贝林格尔.英格海姆国际有限公司 | 人类免疫缺陷病毒复制的抑制剂 |
| ATE541841T1 (de) | 2007-11-15 | 2012-02-15 | Boehringer Ingelheim Int | Inhibitoren der replikation des human immunodeficiency virus |
| NZ585226A (en) | 2007-11-16 | 2012-08-31 | Gilead Sciences Inc | Inhibitors of human immunodeficiency virus replication |
| WO2010011816A1 (en) * | 2008-07-25 | 2010-01-28 | Smithkline Beecham Corporation | Chemical compounds |
| CN103951643B (zh) | 2008-07-25 | 2015-12-09 | 盐野义制药株式会社 | 用作hiv整合酶抑制剂的化合物 |
| WO2010011818A1 (en) * | 2008-07-25 | 2010-01-28 | Smithkline Beecham Corporation | Chemical compounds |
| WO2010011815A1 (en) * | 2008-07-25 | 2010-01-28 | Smithkline Beecham Corporation | Chemical compounds |
| PL2320908T3 (pl) * | 2008-07-25 | 2014-06-30 | Viiv Healthcare Co | Proleki dolutegrawiru |
| MX2011006241A (es) | 2008-12-11 | 2011-06-28 | Shionogi & Co | Sintesis de inhibidores de integrasa de vih de carbamoil-piridona e intermediarios. |
| AU2014277831C1 (en) * | 2008-12-11 | 2022-10-06 | Shionogi & Co. Ltd. | Synthesis of carbamoylpyridone hiv integrase inhibitors and intermediates |
| EP2370419B1 (en) * | 2008-12-11 | 2017-09-27 | Shionogi&Co., Ltd. | Maltol ether processes and intermediates |
| EP2376453B1 (en) | 2008-12-11 | 2019-11-20 | VIIV Healthcare Company | Intermediates for carbamoylpyridone hiv integrase inhibitors |
| TWI518084B (zh) | 2009-03-26 | 2016-01-21 | 鹽野義製藥股份有限公司 | 哌喃酮與吡啶酮衍生物之製造方法 |
| EP2444400B1 (en) | 2009-06-15 | 2018-03-28 | Shionogi&Co., Ltd. | Substituted polycyclic carbamoylpyridone derivative |
| WO2011011483A1 (en) * | 2009-07-22 | 2011-01-27 | Glaxosmithkline Llc | Chemical compounds |
| KR20120087916A (ko) | 2009-10-13 | 2012-08-07 | 엘랑코 애니멀 헬쓰 아일랜드 리미티드 | 마크로시클릭 인테그라제 억제제 |
| AU2014202405B2 (en) * | 2010-01-27 | 2016-02-25 | Viiv Healthcare Company | Antiviral therapy |
| AU2014202404C1 (en) * | 2010-01-27 | 2022-06-23 | Viiv Healthcare Company | Antiviral therapy |
| DK2932970T3 (en) * | 2010-01-27 | 2018-05-28 | Viiv Healthcare Co | ANTIVIRAL THERAPY |
| TWI508968B (zh) * | 2010-02-08 | 2015-11-21 | Biota Scient Management | 用於治療呼吸道融合性病毒感染的化合物 |
| PE20130010A1 (es) | 2010-02-26 | 2013-02-05 | Japan Tobacco Inc | Derivado de 1,3,4,8-tetrahidro-2h-pirido[1,2-a]pirazina como inhibidor de la integrasa del vih |
| TWI582097B (zh) | 2010-03-23 | 2017-05-11 | Ｖｉｉｖ醫療保健公司 | 製備胺甲醯吡啶酮衍生物及中間體之方法 |
| JP5739517B2 (ja) | 2010-04-02 | 2015-06-24 | ヤンセン・アールアンドデイ・アイルランド | 大環状インテグラーゼ阻害剤 |
| US9216995B2 (en) | 2010-04-12 | 2015-12-22 | Shionogi & Co., Ltd. | Pyridone derivative having integrase inhibitory activity |
| WO2012006104A2 (en) | 2010-06-28 | 2012-01-12 | Academia Sinica, Taiwan | Compounds and methods for treating tuberculosis infection |
| PL3456721T3 (pl) | 2010-08-05 | 2021-10-25 | Shionogi & Co., Ltd | Sposób wytwarzania związków wykazujących działanie hamujące integrazę hiv |
| TWI577377B (zh) * | 2010-09-16 | 2017-04-11 | Ｖｉｉｖ醫療保健公司 | 醫藥組合物 |
| RU2608519C2 (ru) * | 2010-09-24 | 2017-01-19 | Шионоги энд Ко. Лтд. | Пролекарственная форма замещенного полициклического производного карбамоилпиридона |
| US8796303B2 (en) | 2010-11-26 | 2014-08-05 | Biota Scientific Management Pty Ltd. | Imidazo[2,1-G][1,7]naphthyridines for treating respiratory syncytial virus infections |
| WO2012151361A1 (en) | 2011-05-03 | 2012-11-08 | Concert Pharmaceuticals Inc. | Carbamoylpyridone derivatives |
| EP2742051B1 (en) | 2011-09-14 | 2016-10-12 | Mapi Pharma Limited | Amorpous form of the dolutegravir sodium salt |
| CA2851218A1 (en) * | 2011-10-12 | 2013-04-18 | Shionogi & Co., Ltd. | Polycyclic pyridone derivative having integrase-inhibiting activity |
| LT2797416T (lt) | 2011-12-28 | 2017-10-25 | Global Blood Therapeutics, Inc. | Pakeistieji benzaldehido junginiai ir jų panaudojimo būdai, didinant audinių aprūpinimą deguonimi |
| WO2013102145A1 (en) | 2011-12-28 | 2013-07-04 | Global Blood Therapeutics, Inc. | Substituted heteroaryl aldehyde compounds and methods for their use in increasing tissue oxygenation |
| WO2014099586A1 (en) * | 2012-12-17 | 2014-06-26 | Merck Sharp & Dohme Corp. | 4-pyridinonetriazine derivatives as hiv integrase inhibitors |
| DK3067358T3 (da) * | 2012-12-21 | 2019-11-04 | Gilead Sciences Inc | Polycykliske carbamoylpyridon-forbindelser og deres farmaceutiske anvendelse |
| JP6320039B2 (ja) | 2012-12-27 | 2018-05-09 | 日本たばこ産業株式会社 | 置換されたスピロピリド［１，２−ａ］ピラジン誘導体及びそのＨＩＶインテグラーゼ阻害剤としての医薬用途 |
| EP2767272A1 (en) | 2013-02-18 | 2014-08-20 | Ratiopharm GmbH | Solid pharmaceutical dosage form of dolutegravir |
| US9480655B2 (en) | 2013-02-18 | 2016-11-01 | Ratiopharm Gmbh | Solid pharmaceutical dosage form of dolutegravir |
| WO2014128545A2 (en) | 2013-02-19 | 2014-08-28 | Aurobindo Pharma Limited | An improved process for the preparation of dolutegravir |
| US10266551B2 (en) | 2013-03-15 | 2019-04-23 | Global Blood Therapeutics, Inc. | Compounds and uses thereof for the modulation of hemoglobin |
| JP6463327B2 (ja) | 2013-03-15 | 2019-01-30 | グローバル ブラッド セラピューティクス インコーポレイテッド | ヘモグロビンの修飾のための化合物及びその使用 |
| PE20161035A1 (es) | 2013-03-15 | 2016-11-13 | Global Blood Therapeutics Inc | Compuestos y usos de estos para la modulacion de la hemoglobina |
| AP2015008718A0 (en) | 2013-03-15 | 2015-09-30 | Global Blood Therapeutics Inc | Compounds and uses thereof for the modulation of hemoglobin |
| US20140274961A1 (en) | 2013-03-15 | 2014-09-18 | Global Blood Therapeutics, Inc. | Compounds and uses thereof for the modulation of hemoglobin |
| US9604999B2 (en) | 2013-03-15 | 2017-03-28 | Global Blood Therapeutics, Inc. | Compounds and uses thereof for the modulation of hemoglobin |
| US8952171B2 (en) | 2013-03-15 | 2015-02-10 | Global Blood Therapeutics, Inc. | Compounds and uses thereof for the modulation of hemoglobin |
| US9458139B2 (en) | 2013-03-15 | 2016-10-04 | Global Blood Therapeutics, Inc. | Compounds and uses thereof for the modulation of hemoglobin |
| WO2014145040A1 (en) | 2013-03-15 | 2014-09-18 | Global Blood Therapeutics, Inc. | Substituted aldehyde compounds and methods for their use in increasing tissue oxygenation |
| US9802900B2 (en) | 2013-03-15 | 2017-10-31 | Global Blood Therapeutics, Inc. | Bicyclic heteroaryl compounds and uses thereof for the modulation of hemoglobin |
| US9422279B2 (en) | 2013-03-15 | 2016-08-23 | Global Blood Therapeutics, Inc. | Compounds and uses thereof for the modulation of hemoglobin |
| WO2014172188A2 (en) | 2013-04-16 | 2014-10-23 | Merck Sharp & Dohme Corp. | 4-pyridone derivative compounds and uses thereof as hiv integrase inhibitors |
| WO2014200880A1 (en) * | 2013-06-13 | 2014-12-18 | Merck Sharp & Dohme Corp. | Fused tricyclic heterocyclic compounds as hiv integrase inhibitors |
| WO2015001572A2 (en) * | 2013-07-04 | 2015-01-08 | Hetero Research Foundation | Process for the preparation of intermediate of dolutegravir |
| NO2865735T3 (enExample) * | 2013-07-12 | 2018-07-21 | ||
| LT3019503T (lt) * | 2013-07-12 | 2017-11-27 | Gilead Sciences, Inc. | Policikliniai karbamoilpiridono junginiai ir jų panaudojimas živ infekcijų gydymui |
| US9856270B2 (en) | 2013-07-17 | 2018-01-02 | Ratiopharm Gmbh | Dolutegravir salts |
| WO2015019310A1 (en) | 2013-08-07 | 2015-02-12 | Mylan Laboratories Ltd | Process for the preparation of dolute-gravir and intermediates thereof |
| WO2015039348A1 (en) * | 2013-09-23 | 2015-03-26 | Merck Sharp & Dohme Corp. | Tetracyclic heterocycle compounds useful as hiv integrase inhibitors |
| EA030695B1 (ru) * | 2013-09-27 | 2018-09-28 | Мерк Шарп И Доум Корп. | Замещенные производные хинолизина, которые можно использовать как ингибиторы интегразы вич |
| EA202092627A1 (ru) | 2013-11-18 | 2021-09-30 | Глобал Блад Терапьютикс, Инк. | Соединения и их применения для модуляции гемоглобина |
| WO2015089847A1 (en) * | 2013-12-20 | 2015-06-25 | Merck Sharp & Dohme Corp. | Spirocyclic heterocycle compounds useful as hiv integrase inhibitors |
| WO2015092752A1 (en) | 2013-12-20 | 2015-06-25 | Mylan Laboratories Ltd. | Novel crystalline form of dolutegravir sodium |
| US9808428B2 (en) | 2014-01-14 | 2017-11-07 | Board Of Regents Of The University Of Nebraska | Compositions and methods for the delivery of therapeutics |
| US9856271B2 (en) | 2014-01-21 | 2018-01-02 | Laurus Labs Limited | Process for the preparation of dolutegravir and pharmaceutically acceptable salts thereof |
| CN114213390A (zh) | 2014-02-07 | 2022-03-22 | 全球血液疗法股份有限公司 | 一种化合物的结晶多晶型物 |
| CN106866701B (zh) * | 2014-03-19 | 2019-03-19 | 杭州普晒医药科技有限公司 | 德罗格韦钠盐的晶型及其制备方法 |
| IN2014MU00916A (enExample) | 2014-03-20 | 2015-09-25 | Cipla Ltd | |
| WO2015177537A1 (en) * | 2014-05-20 | 2015-11-26 | Cipla Limited | Process for preparing polycyclic carbamoyl pyridone derivatives and intermediates thereof |
| TWI677489B (zh) * | 2014-06-20 | 2019-11-21 | 美商基利科學股份有限公司 | 多環型胺甲醯基吡啶酮化合物之合成 |
| NO2717902T3 (enExample) * | 2014-06-20 | 2018-06-23 | ||
| TW201613936A (en) * | 2014-06-20 | 2016-04-16 | Gilead Sciences Inc | Crystalline forms of(2R,5S,13aR)-8-hydroxy-7,9-dioxo-n-(2,4,6-trifluorobenzyl)-2,3,4,5,7,9,13,13a-octahydro-2,5-methanopyrido[1',2':4,5]pyrazino[2,1-b][1,3]oxazepine-10-carboxamide |
| EP3757105B1 (en) | 2014-08-22 | 2024-07-24 | Shionogi & Co., Ltd. | Polycyclic pyridone derivative having integrase inhibitory activity |
| WO2016057866A1 (en) | 2014-10-09 | 2016-04-14 | Board Of Regents Of The University Of Nebraska | Compositions and methods for the delivery of therapeutics |
| WO2016092527A1 (en) * | 2014-12-12 | 2016-06-16 | Sun Pharmaceutical Industries Limited | A process for the preparation of dolutegravir |
| TWI695003B (zh) | 2014-12-23 | 2020-06-01 | 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 |
| WO2016102078A1 (en) | 2014-12-24 | 2016-06-30 | Ratiopharm Gmbh | Solid state forms of dolutegravir sodium |
| EP3045461A1 (en) | 2015-01-16 | 2016-07-20 | LEK Pharmaceuticals d.d. | Processes for preparing dolutegravir and analogues thereof |
| CA2975884A1 (en) | 2015-02-06 | 2016-08-11 | Mylan Laboratories Limited | Processes for the preparation of dolutegravir |
| CZ201599A3 (cs) | 2015-02-13 | 2016-08-24 | Zentiva, K.S. | Pevné formy solí dolutegraviru a způsob jejich přípravy |
| US10081647B2 (en) * | 2015-03-26 | 2018-09-25 | Merck Sharp & Dohme Corp. | Phosphate substituted quinolizine derivatives useful as HIV integrase inhibitors |
| MA41841A (fr) | 2015-03-30 | 2018-02-06 | Global Blood Therapeutics Inc | Composés aldéhyde pour le traitement de la fibrose pulmonaire, de l'hypoxie, et de maladies auto-immunes et des tissus conjonctifs |
| US9630978B2 (en) | 2015-04-02 | 2017-04-25 | Gilead Sciences, Inc. | Polycyclic-carbamoylpyridone compounds and their pharmaceutical use |
| CN112876473A (zh) * | 2015-04-28 | 2021-06-01 | 盐野义制药株式会社 | 经取代的多环性吡啶酮衍生物及其前药 |
| WO2016187788A1 (en) | 2015-05-25 | 2016-12-01 | Merck Sharp & Dohme Corp. | Fused tricyclic heterocyclic compounds useful for treating hiv infection |
| CZ2015537A3 (cs) | 2015-08-04 | 2017-02-15 | Zentiva, K.S. | Pevné formy amorfního dolutegraviru |
| WO2017029642A2 (en) | 2015-08-19 | 2017-02-23 | Laurus Labs Private Limited | Novel polymorphs of dolutegravir and salts thereof |
| SI3346995T1 (sl) | 2015-11-09 | 2019-11-29 | Gilead Sciences Inc | Terapevtski sestavek za zdravljenje virusa človeške imunske pomanjkljivosti |
| WO2017087257A1 (en) | 2015-11-17 | 2017-05-26 | Merck Sharp & Dohme Corp. | Amido-substituted pyridotriazine derivatives useful as hiv integrase inhibitors |
| SI3383392T1 (sl) | 2015-12-04 | 2025-10-30 | Global Blood Therapeutics, Inc. | Režimi odmerjanja za 2-hidroksi-6-((2-(1-izopropil-1h-pirazol-5-il)piridin-3-il)metoksi)benzaldehid |
| WO2017106071A1 (en) | 2015-12-15 | 2017-06-22 | Merck Sharp & Dohme Corp. | Spirocyclic quinolizine derivatives useful as hiv integrase inhibitors |
| ES2742249T3 (es) | 2015-12-21 | 2020-02-13 | Lupin Ltd | Proceso para la preparación de inhibidores de la integrasa de VIH |
| TWI752307B (zh) | 2016-05-12 | 2022-01-11 | 美商全球血液治療公司 | 新穎化合物及製造化合物之方法 |
| WO2017208105A1 (en) | 2016-05-30 | 2017-12-07 | Lupin Limited | Novel crystalline form of dolutegravir sodium |
| EP3474857B1 (en) | 2016-06-23 | 2025-05-21 | VIIV Healthcare Company | Compositions and methods for the delivery of therapeutics |
| ES2952878T3 (es) | 2016-08-08 | 2023-11-06 | Hetero Labs Ltd | Una composición antirretroviral multiclase |
| EP3496718A4 (en) | 2016-08-08 | 2020-01-22 | Hetero Labs Limited | ANTIRETROVIRAL COMPOSITIONS |
| US11091483B2 (en) * | 2016-08-12 | 2021-08-17 | Madera Therapeutics, LLC | Protein kinase regulators |
| WO2018042332A1 (en) | 2016-08-31 | 2018-03-08 | Glaxosmithkline Intellectual Property (No.2) Limited | Combinations and uses and treatments thereof |
| US20190216725A1 (en) * | 2016-09-21 | 2019-07-18 | Merck Shapr & Dohme Corp. | Drug delivery system for the delivery of integrase inhibitors |
| TW202332423A (zh) | 2016-10-12 | 2023-08-16 | 美商全球血液治療公司 | 包含2-羥基-6-((2-(1-異丙基-1h-吡唑-5-基)吡啶-3-基)甲氧基)-苯甲醛之片劑 |
| JOP20190130A1 (ar) * | 2016-12-02 | 2019-06-02 | Merck Sharp & Dohme | مركبات حلقية غير متجانسة رباعية الحلقات مفيدة كمثبطات إنزيم مدمج لفيروس نقص المناعة البشرية (hiv) |
| CN110062627A (zh) | 2016-12-02 | 2019-07-26 | 默沙东公司 | 可用作hiv整合酶抑制剂的三环杂环化合物 |
| WO2018109786A1 (en) | 2016-12-16 | 2018-06-21 | Cipla Limited | Novel polymoprphs and salts of polycyclic carbamoyl pyridone derivatives |
| EP3573984A4 (en) | 2017-01-26 | 2020-07-29 | Merck Sharp & Dohme Corp. | USEFUL SUBSTITUTE QUINOLIZINE DERIVATIVES AS HIV INTEGRASE INHIBITORS |
| EP3583107B1 (en) | 2017-02-16 | 2020-11-18 | Sandoz AG | Crystalline form of cabotegravir sodium |
| EP3363802B1 (en) | 2017-02-16 | 2019-11-20 | Sandoz AG | Crystalline form of cabotegravir sodium |
| WO2019016679A1 (en) * | 2017-07-18 | 2019-01-24 | Viiv Healthcare Company | Combination drug therapy |
| MX2020000790A (es) | 2017-07-21 | 2020-11-11 | Viiv Healthcare Co | Pautas para el tratamiento de infecciones por el vih y sida. |
| EP3661940A1 (en) | 2017-09-07 | 2020-06-10 | Cipla Limited | New polymorphs of dolutegravir sodium |
| US11286262B2 (en) | 2017-10-06 | 2022-03-29 | Shionogi & Co., Ltd. | Stereoselective process for preparing substituted polycyclic pyridone derivatives |
| CA3126348A1 (en) | 2018-01-12 | 2020-07-18 | Board Of Regents Of The University Of Nebraska | Antiviral prodrugs and formulations thereof |
| WO2019159199A1 (en) | 2018-02-16 | 2019-08-22 | Cipla Limited | Continues flow process for the preparation of active pharmaceutical ingredients - polycyclic carbamoyl pyridone derivatives and intermediates thereof |
| US11458136B2 (en) | 2018-04-09 | 2022-10-04 | Board Of Regents Of The University Of Nebraska | Antiviral prodrugs and formulations thereof |
| CN110526930B (zh) | 2018-05-23 | 2022-06-03 | 莫云芬 | 抗hiv病毒的含硫多环-羟基吡啶酮甲酰胺类似物及其应用 |
| EA202092923A1 (ru) * | 2018-05-31 | 2021-04-09 | Сионоги Энд Ко., Лтд. | Полициклическое производное пиридона |
| EA202092921A1 (ru) | 2018-05-31 | 2021-04-07 | Сионоги Энд Ко., Лтд. | Полициклическое производное карбамоилпиридона |
| TWI880373B (zh) * | 2018-05-31 | 2025-04-11 | 日商鹽野義製藥股份有限公司 | 多環性吡啶并三𠯤衍生物 |
| EP3820875B1 (en) | 2018-07-12 | 2024-01-17 | Laurus Labs Limited | A process for purification of protected polycyclic carbamoylpyridone derivatives |
| WO2020072377A1 (en) | 2018-10-01 | 2020-04-09 | Global Blood Therapeutics, Inc. | Modulators of hemoglobin for the treatment of sickle cell disease |
| MX2021004679A (es) | 2018-10-22 | 2021-07-15 | Univ Nebraska | Profarmacos antivirales y nanoformulaciones de las mismas. |
| US20220175936A1 (en) | 2018-11-29 | 2022-06-09 | Board Of Regents Of The University Of Nebraska | Antiviral prodrugs and nanoformulations thereof |
| LT3938047T (lt) | 2019-03-22 | 2022-10-10 | Gilead Sciences, Inc. | Tilteliniai tricikliniai karbamoilpiridono junginiai ir jų naudojimas farmacijoje |
| 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 |
| US20200398978A1 (en) | 2019-06-20 | 2020-12-24 | Bell Helicopter Textron Inc. | Low-drag rotor blade extension |
| US11248005B2 (en) | 2019-07-08 | 2022-02-15 | Lupin Limited | Process for preparation of intermediates used for the synthesis of HIV integrase inhibitor |
| JPWO2021107066A1 (enExample) | 2019-11-28 | 2021-06-03 | ||
| MX2022006940A (es) | 2019-12-09 | 2022-07-11 | Viiv Healthcare Co | Composiciones farmaceuticas. |
| US11697652B2 (en) | 2020-02-24 | 2023-07-11 | Gilead Sciences, Inc. | Tetracyclic compounds and uses thereof |
| WO2025068743A1 (en) | 2023-09-27 | 2025-04-03 | ViiV Healthcare UK (No.3) Limited | Pharmaceutical composition of cabotegravir |
| WO2021209563A1 (en) | 2020-04-16 | 2021-10-21 | Som Innovation Biotech, S.A. | Compounds for use in the treatment of viral infections by respiratory syndrome-related coronavirus |
| WO2022051198A1 (en) | 2020-09-01 | 2022-03-10 | Viiv Healthcare Company | Combination of cabotegravir and levonorgestrel |
| US12421235B2 (en) | 2020-09-30 | 2025-09-23 | Gilead Sciences, Inc. | Bridged tricyclic carbamoylpyridone compounds and uses thereof |
| WO2022079739A1 (en) | 2020-10-14 | 2022-04-21 | Cipla Limited | Fixed dose compositions of cabotegravir and rilpivirine |
| US20250296988A1 (en) | 2020-12-07 | 2025-09-25 | Viiv Healthcare Company | Combination therapy |
| CR20230315A (es) | 2021-01-19 | 2023-09-01 | Gilead Sciences Inc | Compuestos de piridotriazina sustituidos y usos de estos |
| TW202313623A (zh) | 2021-06-03 | 2023-04-01 | 大陸商江蘇恆瑞醫藥股份有限公司 | 具有整合酶抑制活性的吡啶酮化合物及其藥用用途 |
| CN114230579A (zh) * | 2021-11-12 | 2022-03-25 | 南京艾迪医药科技有限公司 | 多环氨基甲酰基吡啶酮衍生物及其制备方法和药物组合物 |
| JP2024542776A (ja) | 2021-12-03 | 2024-11-15 | ヴィーブ、ヘルスケア、カンパニー | （ｒ）－３－アミノブタン－１－オールの合成方法 |
| 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 |
| US20240270756A1 (en) * | 2023-01-18 | 2024-08-15 | Ascletis Bioscience Co., Ltd. | Integrase Inhibitor and Use Thereof |
| WO2025068912A1 (en) | 2023-09-27 | 2025-04-03 | ViiV Healthcare UK (No.3) Limited | Pharmaceutical compositions |
| WO2025128496A1 (en) | 2023-12-12 | 2025-06-19 | Viiv Healthcare Company | Crystalline form |
| WO2025128498A1 (en) | 2023-12-12 | 2025-06-19 | Viiv Healthcare Company | Pharmaceutical compositions |
| WO2025181723A1 (en) | 2024-03-01 | 2025-09-04 | ViiV Healthcare UK (No.3) Limited | Dosing regimen |
Family Cites Families (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3959316A (en) * | 1972-03-13 | 1976-05-25 | Snam Progetti S.P.A. | Procedure for propylene oxide synthesis |
| JPH0296506A (ja) | 1988-09-30 | 1990-04-09 | Daicel Chem Ind Ltd | 除草剤組成物 |
| JP2533796B2 (ja) * | 1988-10-18 | 1996-09-11 | ダイセル化学工業株式会社 | ５−アルコキシピリジン−３−カルボキサミド誘導体とその製造方法及び植物成長抑制剤 |
| JP2551472B2 (ja) | 1988-10-18 | 1996-11-06 | ダイセル化学工業株式会社 | ５−アルコキシ−γ−ピロン−３−カルボキサミド誘導体とその製造方法及び植物成長抑制剤 |
| BR9814323A (pt) | 1997-12-22 | 2004-06-29 | Upjohn Co | 4-hidroxiquinolina-3-carboxamidas e hidrazidas como agentes antiviróticos |
| AU2001262732A1 (en) † | 2000-06-14 | 2001-12-24 | Shionogi And Co., Ltd. | Inhibitor for enzyme having two divalent metal ions as active centers |
| US6580562B2 (en) | 2000-07-24 | 2003-06-17 | Yazaki Corporation | On-vehicle display unit |
| US6384263B1 (en) | 2000-08-04 | 2002-05-07 | E. I. Du Pont De Nemours And Company | Process for making 3-hydroxyalkanelnitriles and conversion of the 3-hydroxyalkanelnitrile to an hydroxyaminoalkane |
| JP4287649B2 (ja) | 2000-10-12 | 2009-07-01 | メルク エンド カムパニー インコーポレーテッド | Ｈｉｖインテグラーゼ阻害薬として有用なアザ−およびポリアザ−ナフタレニルカルボキサミド類 |
| JP2003032772A (ja) | 2001-07-12 | 2003-01-31 | Foster Electric Co Ltd | 耳掛け式イヤホン |
| BR0211750A (pt) | 2001-08-10 | 2004-10-13 | Shionogi & Co | Agente antiviral |
| DE60218511T2 (de) | 2001-10-26 | 2007-10-25 | Istituto Di Richerche Di Biologia Molecolare P. Angeletti S.P.A. | Dihydroxypyrimidin-carbonsäueramid-hemmer der hiv-integrase |
| MXPA04003932A (es) | 2001-10-26 | 2004-06-18 | Angeletti P Ist Richerche Bio | Inhibidores de la hidroxipirimidinona carboxamida n-sustituida de la integrasa del virus de inmunodeficiencia humana. |
| US7279487B2 (en) | 2002-01-17 | 2007-10-09 | Merck & Co., Inc. | Hydroxynaphthyridinone carboxamides useful as HIV integrase inhibitors |
| US7109186B2 (en) | 2002-07-09 | 2006-09-19 | Bristol-Myers Squibb Company | HIV integrase inhibitors |
| WO2004024693A1 (ja) | 2002-08-13 | 2004-03-25 | Shionogi & Co., Ltd. | Ｈｉｖインテグラーゼ阻害活性を有するヘテロ環化合物 |
| WO2004024078A2 (en) * | 2002-09-11 | 2004-03-25 | Merck & Co., Inc. | Dihydroxypyridopyrazine-1,6-dione compounds useful as hiv integrase inhibitors |
| DE60334248D1 (de) * | 2002-12-27 | 2010-10-28 | Angeletti P Ist Richerche Bio | Tetrahydro-4h-pyridoä1,2-aüpyrimidine und verwandte verbindungen verwendbar als hiv integrase hemmer |
| US6960680B2 (en) | 2003-01-08 | 2005-11-01 | Rhodia Chirex, Inc. | Manufacture of water-soluble β-hydroxynitriles |
| JP2004244320A (ja) | 2003-02-10 | 2004-09-02 | Shionogi & Co Ltd | 含窒素複素環抗ウイルス剤 |
| JP2006528694A (ja) | 2003-05-13 | 2006-12-21 | スミスクライン ビーチャム コーポレーション | ナフチリジンインテグラーゼインヒビター |
| AU2003273190A1 (en) * | 2003-08-12 | 2005-02-25 | Rachel Beijer | Scheduled message service |
| TW200510425A (en) * | 2003-08-13 | 2005-03-16 | Japan Tobacco Inc | Nitrogen-containing fused ring compound and use thereof as HIV integrase inhibitor |
| JP4530642B2 (ja) | 2003-10-31 | 2010-08-25 | オリンパス株式会社 | 内視鏡装置 |
| JP4859676B2 (ja) | 2004-02-11 | 2012-01-25 | スミスクライン ビーチャム コーポレーション | Ｈｉｖインテグラーゼ阻害剤 |
| JP2007528379A (ja) | 2004-03-09 | 2007-10-11 | イステイチユート・デイ・リチエルケ・デイ・ビオロジア・モレコラーレ・ピ・アンジエレツテイ・エツセ・ピー・アー | Ｈｉｖインテグラーゼ阻害薬 |
| EP1725102A4 (en) | 2004-03-09 | 2009-04-29 | Merck & Co Inc | HIV integrase |
| AU2005244157B2 (en) | 2004-05-07 | 2010-11-11 | Merck Sharp & Dohme Corp. | HIV integrase inhibitors |
| EP1973906A1 (en) | 2004-12-23 | 2008-10-01 | Virochem Pharma Inc. | Hydroxydihydropyridopy razine-1,8-diones and methods for inhibiting hiv integrase |
| WO2006088173A1 (ja) | 2005-02-21 | 2006-08-24 | Shionogi & Co., Ltd. | Ｈｉｖインテグラーゼ阻害活性を有する２環性カルバモイルピリドン誘導体 |
| US7981879B2 (en) | 2005-03-31 | 2011-07-19 | Instituto di Ricerchi di Biologia Molecolare P. Angeletti S.p.A. | HIV integrase inhibitors |
| ES2567197T3 (es) * | 2005-04-28 | 2016-04-20 | Viiv Healthcare Company | Derivado de carbamoilpiridona policíclico que tiene actividad inhibidora de la integrasa del VIH |
| JP2005312076A (ja) | 2005-05-26 | 2005-11-04 | Olympus Corp | 電子撮像装置 |
| JP2009503081A (ja) | 2005-08-04 | 2009-01-29 | スミスクライン ビーチャム コーポレーション | Ｈｉｖインテグラーゼ阻害薬 |
| KR20080064182A (ko) | 2005-10-27 | 2008-07-08 | 시오노기세야쿠 가부시키가이샤 | Ｈｉｖ 인테그라아제 억제활성을 가지는 다환성카르바모일피리돈 유도체 |
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2024
- 2024-04-09 US US18/630,561 patent/US20240279238A1/en not_active Abandoned
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