ES2623777T3 - Inhibidores de la replicación del virus de la inmunodeficiencia humana - Google Patents
Inhibidores de la replicación del virus de la inmunodeficiencia humana Download PDFInfo
- Publication number
- ES2623777T3 ES2623777T3 ES14725559.0T ES14725559T ES2623777T3 ES 2623777 T3 ES2623777 T3 ES 2623777T3 ES 14725559 T ES14725559 T ES 14725559T ES 2623777 T3 ES2623777 T3 ES 2623777T3
- Authority
- ES
- Spain
- Prior art keywords
- alkyl
- equiv
- mmol
- haloalkyl
- methylimidazo
- Prior art date
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- 239000003112 inhibitor Substances 0.000 title description 16
- 241000725303 Human immunodeficiency virus Species 0.000 title description 10
- 230000029812 viral genome replication Effects 0.000 title 1
- -1 homopiperidinyl Chemical group 0.000 abstract description 33
- 150000001875 compounds Chemical class 0.000 abstract description 14
- 150000003839 salts Chemical class 0.000 abstract description 10
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 5
- 239000001257 hydrogen Substances 0.000 abstract description 5
- 125000000217 alkyl group Chemical group 0.000 abstract 15
- 125000001188 haloalkyl group Chemical group 0.000 abstract 5
- 125000003342 alkenyl group Chemical group 0.000 abstract 4
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 4
- 125000001475 halogen functional group Chemical group 0.000 abstract 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 4
- 125000001424 substituent group Chemical group 0.000 abstract 4
- 125000003545 alkoxy group Chemical group 0.000 abstract 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 abstract 2
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 2
- 125000004438 haloalkoxy group Chemical group 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- 125000003302 alkenyloxy group Chemical group 0.000 abstract 1
- 125000002393 azetidinyl group Chemical group 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 abstract 1
- 125000000392 cycloalkenyl group Chemical group 0.000 abstract 1
- 125000002541 furyl group Chemical group 0.000 abstract 1
- 125000002883 imidazolyl group Chemical group 0.000 abstract 1
- 125000001786 isothiazolyl group Chemical group 0.000 abstract 1
- 125000000842 isoxazolyl group Chemical group 0.000 abstract 1
- 125000002757 morpholinyl group Chemical group 0.000 abstract 1
- 125000001715 oxadiazolyl group Chemical group 0.000 abstract 1
- 125000002971 oxazolyl group Chemical group 0.000 abstract 1
- 125000004193 piperazinyl group Chemical group 0.000 abstract 1
- 125000003386 piperidinyl group Chemical group 0.000 abstract 1
- 125000003226 pyrazolyl group Chemical group 0.000 abstract 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 abstract 1
- 125000000168 pyrrolyl group Chemical group 0.000 abstract 1
- 125000001113 thiadiazolyl group Chemical group 0.000 abstract 1
- 125000000335 thiazolyl group Chemical group 0.000 abstract 1
- 125000001544 thienyl group Chemical group 0.000 abstract 1
- 125000001425 triazolyl group Chemical group 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
- 238000006243 chemical reaction Methods 0.000 description 39
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 30
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 29
- 239000000243 solution Substances 0.000 description 24
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 23
- 239000000203 mixture Substances 0.000 description 22
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 20
- 235000019439 ethyl acetate Nutrition 0.000 description 19
- 239000000047 product Substances 0.000 description 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 239000012043 crude product Substances 0.000 description 16
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 238000005160 1H NMR spectroscopy Methods 0.000 description 14
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
- 239000003795 chemical substances by application Substances 0.000 description 14
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 13
- 239000007832 Na2SO4 Substances 0.000 description 12
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 229910052938 sodium sulfate Inorganic materials 0.000 description 12
- 235000011152 sodium sulphate Nutrition 0.000 description 12
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- 125000005336 allyloxy group Chemical group 0.000 description 11
- 238000003818 flash chromatography Methods 0.000 description 11
- 238000000034 method Methods 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 8
- 239000005695 Ammonium acetate Substances 0.000 description 8
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 229940043376 ammonium acetate Drugs 0.000 description 8
- 235000019257 ammonium acetate Nutrition 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- 239000012071 phase Substances 0.000 description 8
- RUZLIIJDZBWWSA-INIZCTEOSA-N methyl 2-[[(1s)-1-(7-methyl-2-morpholin-4-yl-4-oxopyrido[1,2-a]pyrimidin-9-yl)ethyl]amino]benzoate Chemical group COC(=O)C1=CC=CC=C1N[C@@H](C)C1=CC(C)=CN2C(=O)C=C(N3CCOCC3)N=C12 RUZLIIJDZBWWSA-INIZCTEOSA-N 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
- 235000017557 sodium bicarbonate Nutrition 0.000 description 7
- 159000000000 sodium salts Chemical class 0.000 description 7
- 208000030507 AIDS Diseases 0.000 description 6
- 208000031886 HIV Infections Diseases 0.000 description 6
- 208000037357 HIV infectious disease Diseases 0.000 description 6
- 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
- ZTMVKMHUHTXAAI-SFHVURJKSA-N 5-(4,4-dimethylpiperidin-1-yl)-6-[(1S)-2-methoxy-1-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]-7-methylimidazo[1,2-a]pyridine-2-carboxylic acid Chemical compound COC(=O)[C@@H](OC(C)(C)C)c1c(C)cc2nc(cn2c1N1CCC(C)(C)CC1)C(O)=O ZTMVKMHUHTXAAI-SFHVURJKSA-N 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
- 239000007821 HATU Substances 0.000 description 5
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 5
- 239000002027 dichloromethane extract Substances 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- 125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 4
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 102100035875 C-C chemokine receptor type 5 Human genes 0.000 description 3
- 101710149870 C-C chemokine receptor type 5 Proteins 0.000 description 3
- 102100031650 C-X-C chemokine receptor type 4 Human genes 0.000 description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
- 101000922348 Homo sapiens C-X-C chemokine receptor type 4 Proteins 0.000 description 3
- 229940124522 antiretrovirals Drugs 0.000 description 3
- 239000003903 antiretrovirus agent Substances 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 239000004030 hiv protease inhibitor Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000004949 mass spectrometry Methods 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- SWWHMIZLLVXNME-UHFFFAOYSA-N tert-butyl 6-amino-2-chloro-4-methylpyridine-3-carboxylate Chemical compound Cc1cc(N)nc(Cl)c1C(=O)OC(C)(C)C SWWHMIZLLVXNME-UHFFFAOYSA-N 0.000 description 3
- 239000003981 vehicle Substances 0.000 description 3
- CXNIUSPIQKWYAI-UHFFFAOYSA-N xantphos Chemical compound C=12OC3=C(P(C=4C=CC=CC=4)C=4C=CC=CC=4)C=CC=C3C(C)(C)C2=CC=CC=1P(C=1C=CC=CC=1)C1=CC=CC=C1 CXNIUSPIQKWYAI-UHFFFAOYSA-N 0.000 description 3
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- DYAAHGCWBJBFLL-UHFFFAOYSA-N 5-chloro-2-ethoxycarbonyl-7-methylimidazo[1,2-a]pyridine-6-carboxylic acid Chemical compound CCOC(=O)c1cn2c(Cl)c(C(O)=O)c(C)cc2n1 DYAAHGCWBJBFLL-UHFFFAOYSA-N 0.000 description 2
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- WHBIGIKBNXZKFE-UHFFFAOYSA-N delavirdine Chemical group CC(C)NC1=CC=CN=C1N1CCN(C(=O)C=2NC3=CC=C(NS(C)(=O)=O)C=C3C=2)CC1 WHBIGIKBNXZKFE-UHFFFAOYSA-N 0.000 description 2
- SXZIXHOMFPUIRK-UHFFFAOYSA-N diphenylmethanimine Chemical compound C=1C=CC=CC=1C(=N)C1=CC=CC=C1 SXZIXHOMFPUIRK-UHFFFAOYSA-N 0.000 description 2
- VICYTAYPKBLQFB-UHFFFAOYSA-N ethyl 3-bromo-2-oxopropanoate Chemical compound CCOC(=O)C(=O)CBr VICYTAYPKBLQFB-UHFFFAOYSA-N 0.000 description 2
- DJQPQGOIQVKXER-UHFFFAOYSA-N ethyl 5-chloro-6-(2-methoxy-2-oxoacetyl)-7-methylimidazo[1,2-a]pyridine-2-carboxylate Chemical compound CCOC(=O)c1cn2c(Cl)c(C(=O)C(=O)OC)c(C)cc2n1 DJQPQGOIQVKXER-UHFFFAOYSA-N 0.000 description 2
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- 229940040692 lithium hydroxide monohydrate Drugs 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
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- 239000000463 material Substances 0.000 description 2
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- NQDJXKOVJZTUJA-UHFFFAOYSA-N nevirapine Chemical compound C12=NC=CC=C2C(=O)NC=2C(C)=CC=NC=2N1C1CC1 NQDJXKOVJZTUJA-UHFFFAOYSA-N 0.000 description 2
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- ASSJTMUEFHUKMJ-UHFFFAOYSA-N 1-acetyl-n-[3-[4-[(4-carbamoylphenyl)methyl]piperidin-1-yl]propyl]-n-(3-chloro-4-methylphenyl)piperidine-4-carboxamide Chemical compound C1CN(C(=O)C)CCC1C(=O)N(C=1C=C(Cl)C(C)=CC=1)CCCN1CCC(CC=2C=CC(=CC=2)C(N)=O)CC1 ASSJTMUEFHUKMJ-UHFFFAOYSA-N 0.000 description 1
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- MDDXDIWSPBEWEB-UHFFFAOYSA-N tert-butyl 6-amino-2-(4,4-dimethylpiperidin-1-yl)-4-methylpyridine-3-carboxylate Chemical compound Cc1cc(N)nc(N2CCC(C)(C)CC2)c1C(=O)OC(C)(C)C MDDXDIWSPBEWEB-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—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
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/4545—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring hetero atom, e.g. pipamperone, anabasine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Virology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Tropical Medicine & Parasitology (AREA)
- Communicable Diseases (AREA)
- Molecular Biology (AREA)
- Oncology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- AIDS & HIV (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361780179P | 2013-03-13 | 2013-03-13 | |
| US201361780179P | 2013-03-13 | ||
| PCT/US2014/022354 WO2014164409A1 (en) | 2013-03-13 | 2014-03-10 | Inhibitors of human immunodeficiency virus replication |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2623777T3 true ES2623777T3 (es) | 2017-07-12 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES14725559.0T Active ES2623777T3 (es) | 2013-03-13 | 2014-03-10 | Inhibidores de la replicación del virus de la inmunodeficiencia humana |
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| Country | Link |
|---|---|
| US (1) | US9655889B2 (OSRAM) |
| EP (1) | EP2970273B1 (OSRAM) |
| JP (1) | JP2016512507A (OSRAM) |
| CN (1) | CN105008358B (OSRAM) |
| ES (1) | ES2623777T3 (OSRAM) |
| WO (1) | WO2014164409A1 (OSRAM) |
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| US9409922B2 (en) | 2014-02-18 | 2016-08-09 | Bristol-Myers Squibb Company | Imidazopyridine macrocycles as inhibitors of human immunodeficiency virus replication |
| PT3107913T (pt) | 2014-02-19 | 2018-09-28 | Viiv Healthcare Uk No 5 Ltd | Inibidores da replicação do vírus da imunodeficiência humana |
| JP6579549B2 (ja) | 2014-05-16 | 2019-09-25 | 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 |
| CN107001357A (zh) * | 2014-08-27 | 2017-08-01 | Viiv保健英国第五有限公司 | 用作人免疫缺陷病毒复制抑制剂的咪唑并[1,2‑a]吡啶衍生物 |
| WO2016119700A1 (en) | 2015-01-28 | 2016-08-04 | Jn Therapeutics | Substituted imidazo [1, 2-a] pyridin-2-ylamine compounds, and pharmaceutical compositions and methods of use thereof |
| CA2987384A1 (en) | 2015-05-29 | 2016-12-08 | Shionogi & Co., Ltd. | Nitrogen-containing tricyclic derivative having hiv replication inhibitory activity |
| KR20180025928A (ko) * | 2015-07-06 | 2018-03-09 | 비브 헬스케어 유케이 (넘버5) 리미티드 | 인간 면역결핍 바이러스 복제의 억제제로서 피리딘-3-일 아세트산 유도체 |
| WO2017006260A1 (en) * | 2015-07-08 | 2017-01-12 | VIIV Healthcare UK (No.5) Limited | Pyridin-3-yl acetic acid derivatives as inhibitors of human immunodeficiency virus replication |
| CA2994517A1 (en) | 2015-08-10 | 2017-02-16 | VIIV Healthcare UK (No.5) Limited | Imidazopyridine macrocycles as inhibitors of human immunodeficiency virus replication |
| US20230295160A1 (en) * | 2020-08-14 | 2023-09-21 | Shanghai Fudan-Zhangjiang Bio-Pharmaceutical Co., Ltd. | Salt form and crystal form of jak inhibitor, preparation method therefor, and use thereof |
| CN113698342B (zh) * | 2021-10-29 | 2021-12-31 | 南京恒远科技开发有限公司 | 一种奥布替尼关键中间体杂环类化合物2,6-二氯烟酸的制备方法 |
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| KR910011852A (ko) * | 1989-12-04 | 1991-08-07 | 폴 디. 매튜카이티스 | 신경독 장해 치료용 이미다조[1,2-a]피리디닐알킬 화합물 |
| PL369531A1 (en) | 2001-09-26 | 2005-05-02 | Bayer Pharmaceuticals Corporation | 1,8-naphthyridine derivatives as antidiabetics |
| EP1919872A4 (en) * | 2005-08-31 | 2009-08-05 | Smithkline Beecham Corp | CHEMICAL COMPOUNDS |
| US7939545B2 (en) | 2006-05-16 | 2011-05-10 | Boehringer Ingelheim International Gmbh | Inhibitors of human immunodeficiency virus replication |
| RU2503679C2 (ru) | 2007-11-15 | 2014-01-10 | Джилид Сайенсиз, Инк. | Ингибиторы репликации вируса иммунодефицита человека |
| US8377960B2 (en) | 2007-11-15 | 2013-02-19 | Gilead Sciences, Inc. | Inhibitors of human immunodeficiency virus replication |
| WO2009062285A1 (en) | 2007-11-16 | 2009-05-22 | Boehringer Ingelheim International Gmbh | Inhibitors of human immunodeficiency virus replication |
| CA2705338A1 (en) * | 2007-11-16 | 2009-05-22 | Boehringer Ingelheim International Gmbh | Inhibitors of human immunodeficiency virus replication |
| WO2010032195A1 (en) * | 2008-09-16 | 2010-03-25 | Csir | Imidazopyridines and imidazopyrimidines as hiv-i reverse transcriptase inhibitors |
| GB0908394D0 (en) | 2009-05-15 | 2009-06-24 | Univ Leuven Kath | Novel viral replication inhibitors |
| US8338441B2 (en) * | 2009-05-15 | 2012-12-25 | Gilead Sciences, Inc. | Inhibitors of human immunodeficiency virus replication |
| GB0913636D0 (en) | 2009-08-05 | 2009-09-16 | Univ Leuven Kath | Novel viral replication inhibitors |
| ES2475970T3 (es) | 2009-12-23 | 2014-07-11 | Katholieke Universiteit Leuven | Novedosos compuestos antivirales |
| MA34397B1 (fr) | 2010-07-02 | 2013-07-03 | Gilead Sciences Inc | Dérivés d'acide napht-2-ylacétique dans le traitement du sida |
| WO2012003498A1 (en) | 2010-07-02 | 2012-01-05 | Gilead Sciences, Inc. | 2 -quinolinyl- acetic acid derivatives as hiv antiviral compounds |
| US8633200B2 (en) | 2010-09-08 | 2014-01-21 | Bristol-Myers Squibb Company | Inhibitors of human immunodeficiency virus replication |
| BR112013011991A2 (pt) | 2010-11-15 | 2016-08-30 | Viiv Healthcare Uk Ltd | composto, composição farmacêutica, uso de um composto, método de tratamento, produto, e kit. |
| KR20140003438A (ko) | 2010-11-15 | 2014-01-09 | 카톨리에케 유니버시테이트 루벤 | 항바이러스성 축합 헤테로사이클릭 화합물 |
| US8791108B2 (en) * | 2011-08-18 | 2014-07-29 | Bristol-Myers Squibb Company | Inhibitors of human immunodeficiency virus replication |
-
2014
- 2014-03-10 ES ES14725559.0T patent/ES2623777T3/es active Active
- 2014-03-10 US US14/770,702 patent/US9655889B2/en not_active Expired - Fee Related
- 2014-03-10 JP JP2016500947A patent/JP2016512507A/ja active Pending
- 2014-03-10 WO PCT/US2014/022354 patent/WO2014164409A1/en not_active Ceased
- 2014-03-10 CN CN201480013594.8A patent/CN105008358B/zh not_active Expired - Fee Related
- 2014-03-10 EP EP14725559.0A patent/EP2970273B1/en not_active Not-in-force
Also Published As
| Publication number | Publication date |
|---|---|
| CN105008358A (zh) | 2015-10-28 |
| WO2014164409A1 (en) | 2014-10-09 |
| CN105008358B (zh) | 2017-12-29 |
| JP2016512507A (ja) | 2016-04-28 |
| US20160000771A1 (en) | 2016-01-07 |
| EP2970273A1 (en) | 2016-01-20 |
| EP2970273B1 (en) | 2017-03-01 |
| US9655889B2 (en) | 2017-05-23 |
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