MX2014014766A - Inhibidores macrociclicos de virus flaviviridae. - Google Patents
Inhibidores macrociclicos de virus flaviviridae.Info
- Publication number
- MX2014014766A MX2014014766A MX2014014766A MX2014014766A MX2014014766A MX 2014014766 A MX2014014766 A MX 2014014766A MX 2014014766 A MX2014014766 A MX 2014014766A MX 2014014766 A MX2014014766 A MX 2014014766A MX 2014014766 A MX2014014766 A MX 2014014766A
- Authority
- MX
- Mexico
- Prior art keywords
- mmol
- compound
- alkyl
- mixture
- ethyl acetate
- Prior art date
Links
- 239000003112 inhibitor Substances 0.000 title claims description 47
- 241000710781 Flaviviridae Species 0.000 title claims description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 326
- 239000000203 mixture Substances 0.000 claims abstract description 142
- 238000000034 method Methods 0.000 claims abstract description 55
- 150000002148 esters Chemical class 0.000 claims abstract description 44
- 150000003839 salts Chemical class 0.000 claims abstract description 43
- 238000011282 treatment Methods 0.000 claims abstract description 29
- 230000009385 viral infection Effects 0.000 claims abstract description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 82
- 125000003118 aryl group Chemical group 0.000 claims description 68
- 125000001424 substituent group Chemical group 0.000 claims description 56
- 125000005843 halogen group Chemical group 0.000 claims description 50
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 38
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 35
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 30
- 229940002612 prodrug Drugs 0.000 claims description 30
- 239000000651 prodrug Chemical class 0.000 claims description 30
- 125000004429 atom Chemical group 0.000 claims description 27
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 23
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 22
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 22
- 229910052799 carbon Inorganic materials 0.000 claims description 21
- 125000003342 alkenyl group Chemical group 0.000 claims description 20
- 201000010099 disease Diseases 0.000 claims description 20
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 20
- 125000001589 carboacyl group Chemical group 0.000 claims description 18
- 208000036142 Viral infection Diseases 0.000 claims description 15
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 14
- 239000003814 drug Substances 0.000 claims description 13
- 239000002777 nucleoside Substances 0.000 claims description 12
- 125000000732 arylene group Chemical group 0.000 claims description 11
- 150000003833 nucleoside derivatives Chemical class 0.000 claims description 11
- LHHCSNFAOIFYRV-DOVBMPENSA-N boceprevir Chemical group O=C([C@@H]1[C@@H]2[C@@H](C2(C)C)CN1C(=O)[C@@H](NC(=O)NC(C)(C)C)C(C)(C)C)NC(C(=O)C(N)=O)CC1CCC1 LHHCSNFAOIFYRV-DOVBMPENSA-N 0.000 claims description 10
- 206010014599 encephalitis Diseases 0.000 claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims description 9
- 125000001188 haloalkyl group Chemical group 0.000 claims description 8
- 125000005549 heteroarylene group Chemical group 0.000 claims description 8
- 229960000517 boceprevir Drugs 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 241000711573 Coronaviridae Species 0.000 claims description 5
- 241000700605 Viruses Species 0.000 claims description 5
- 208000015181 infectious disease Diseases 0.000 claims description 5
- 239000002773 nucleotide Substances 0.000 claims description 5
- 125000003729 nucleotide group Chemical group 0.000 claims description 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
- 229940124597 therapeutic agent Drugs 0.000 claims description 5
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 4
- 230000001225 therapeutic effect Effects 0.000 claims description 4
- 208000030507 AIDS Diseases 0.000 claims description 3
- 201000003176 Severe Acute Respiratory Syndrome Diseases 0.000 claims description 3
- 230000002519 immonomodulatory effect Effects 0.000 claims description 3
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 3
- 241000700721 Hepatitis B virus Species 0.000 claims description 2
- 208000006454 hepatitis Diseases 0.000 claims 3
- 231100000283 hepatitis Toxicity 0.000 claims 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims 3
- AWGBKZRMLNVLAF-UHFFFAOYSA-N 3,5-dibromo-n,2-dihydroxybenzamide Chemical compound ONC(=O)C1=CC(Br)=CC(Br)=C1O AWGBKZRMLNVLAF-UHFFFAOYSA-N 0.000 claims 1
- 206010037660 Pyrexia Diseases 0.000 claims 1
- 239000000556 agonist Substances 0.000 claims 1
- 125000005741 alkyl alkenyl group Chemical group 0.000 claims 1
- 230000008520 organization Effects 0.000 claims 1
- 208000005176 Hepatitis C Diseases 0.000 abstract description 3
- 208000010710 hepatitis C virus infection Diseases 0.000 abstract description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 569
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 296
- 235000019439 ethyl acetate Nutrition 0.000 description 189
- 239000000243 solution Substances 0.000 description 189
- -1 cyano, hydroxy Chemical group 0.000 description 169
- 239000011541 reaction mixture Substances 0.000 description 156
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 148
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 144
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 139
- 239000007787 solid Substances 0.000 description 123
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 118
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 117
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 116
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 109
- 239000000741 silica gel Substances 0.000 description 105
- 229910002027 silica gel Inorganic materials 0.000 description 105
- 238000006243 chemical reaction Methods 0.000 description 104
- YUHZIUAREWNXJT-UHFFFAOYSA-N (2-fluoropyridin-3-yl)boronic acid Chemical class OB(O)C1=CC=CN=C1F YUHZIUAREWNXJT-UHFFFAOYSA-N 0.000 description 103
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 103
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 102
- 229910001868 water Inorganic materials 0.000 description 99
- 238000004587 chromatography analysis Methods 0.000 description 96
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 84
- 229910052757 nitrogen Inorganic materials 0.000 description 78
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 62
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 57
- 239000002253 acid Substances 0.000 description 57
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 56
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 50
- 229960003010 sodium sulfate Drugs 0.000 description 49
- 229910052938 sodium sulfate Inorganic materials 0.000 description 49
- 235000011152 sodium sulphate Nutrition 0.000 description 49
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 43
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 43
- 239000012267 brine Substances 0.000 description 42
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 42
- 239000000047 product Substances 0.000 description 40
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 39
- 239000010410 layer Substances 0.000 description 39
- 125000000753 cycloalkyl group Chemical group 0.000 description 37
- 238000003756 stirring Methods 0.000 description 37
- 125000003545 alkoxy group Chemical group 0.000 description 34
- 239000003921 oil Substances 0.000 description 34
- 235000019198 oils Nutrition 0.000 description 33
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 29
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 27
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 26
- 239000012044 organic layer Substances 0.000 description 26
- 239000002904 solvent Substances 0.000 description 26
- 241000711549 Hepacivirus C Species 0.000 description 24
- 239000003039 volatile agent Substances 0.000 description 23
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 22
- 125000001072 heteroaryl group Chemical group 0.000 description 22
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 21
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 21
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 21
- 125000004432 carbon atom Chemical group C* 0.000 description 21
- ZRPFJAPZDXQHSM-UHFFFAOYSA-L 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazole;dichloro-[(2-propan-2-yloxyphenyl)methylidene]ruthenium Chemical compound CC(C)OC1=CC=CC=C1C=[Ru](Cl)(Cl)=C1N(C=2C(=CC(C)=CC=2C)C)CCN1C1=C(C)C=C(C)C=C1C ZRPFJAPZDXQHSM-UHFFFAOYSA-L 0.000 description 20
- 150000001336 alkenes Chemical class 0.000 description 20
- 150000001412 amines Chemical class 0.000 description 20
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 20
- 235000019341 magnesium sulphate Nutrition 0.000 description 20
- 239000002585 base Substances 0.000 description 19
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 18
- 238000005481 NMR spectroscopy Methods 0.000 description 18
- 125000004663 dialkyl amino group Chemical group 0.000 description 18
- 239000000284 extract Substances 0.000 description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 18
- 229920006395 saturated elastomer Polymers 0.000 description 18
- 229940086542 triethylamine Drugs 0.000 description 18
- 238000010992 reflux Methods 0.000 description 17
- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 description 16
- 150000002576 ketones Chemical class 0.000 description 16
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 16
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 description 15
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 description 15
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 15
- 239000000725 suspension Substances 0.000 description 15
- FTVLMFQEYACZNP-UHFFFAOYSA-N trimethylsilyl trifluoromethanesulfonate Chemical compound C[Si](C)(C)OS(=O)(=O)C(F)(F)F FTVLMFQEYACZNP-UHFFFAOYSA-N 0.000 description 15
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 15
- 229920002554 vinyl polymer Polymers 0.000 description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 14
- 125000000304 alkynyl group Chemical group 0.000 description 14
- 239000012258 stirred mixture Substances 0.000 description 14
- 239000000706 filtrate Substances 0.000 description 13
- 239000012299 nitrogen atmosphere Substances 0.000 description 13
- 150000002894 organic compounds Chemical class 0.000 description 13
- 238000005160 1H NMR spectroscopy Methods 0.000 description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- IWUCXVSUMQZMFG-AFCXAGJDSA-N Ribavirin Chemical compound N1=C(C(=O)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 IWUCXVSUMQZMFG-AFCXAGJDSA-N 0.000 description 12
- 239000003054 catalyst Substances 0.000 description 12
- 238000005859 coupling reaction Methods 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- 239000002243 precursor Substances 0.000 description 12
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 11
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 11
- 239000012071 phase Substances 0.000 description 11
- 239000000843 powder Substances 0.000 description 11
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 10
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 10
- 150000001299 aldehydes Chemical class 0.000 description 10
- XRWSZZJLZRKHHD-WVWIJVSJSA-N asunaprevir Chemical compound O=C([C@@H]1C[C@H](CN1C(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)(C)C)OC1=NC=C(C2=CC=C(Cl)C=C21)OC)N[C@]1(C(=O)NS(=O)(=O)C2CC2)C[C@H]1C=C XRWSZZJLZRKHHD-WVWIJVSJSA-N 0.000 description 10
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 10
- 239000000460 chlorine Substances 0.000 description 10
- 239000012230 colorless oil Substances 0.000 description 10
- 230000008878 coupling Effects 0.000 description 10
- 238000010168 coupling process Methods 0.000 description 10
- 229910052805 deuterium Inorganic materials 0.000 description 10
- 229910052736 halogen Inorganic materials 0.000 description 10
- 229910052739 hydrogen Inorganic materials 0.000 description 10
- 239000001257 hydrogen Substances 0.000 description 10
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 10
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 10
- 125000006239 protecting group Chemical group 0.000 description 10
- 150000003254 radicals Chemical class 0.000 description 10
- 238000006798 ring closing metathesis reaction Methods 0.000 description 10
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 10
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 10
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 150000001408 amides Chemical class 0.000 description 9
- 239000008346 aqueous phase Substances 0.000 description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 9
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
- 239000005457 ice water Substances 0.000 description 9
- GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium hydroxide monohydrate Substances [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 description 9
- 229910052760 oxygen Inorganic materials 0.000 description 9
- 230000002829 reductive effect Effects 0.000 description 9
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 9
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 8
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 8
- 239000004280 Sodium formate Substances 0.000 description 8
- 150000001345 alkine derivatives Chemical class 0.000 description 8
- 238000010511 deprotection reaction Methods 0.000 description 8
- 229940079593 drug Drugs 0.000 description 8
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 8
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 8
- MXQOYLRVSVOCQT-UHFFFAOYSA-N palladium;tritert-butylphosphane Chemical compound [Pd].CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C MXQOYLRVSVOCQT-UHFFFAOYSA-N 0.000 description 8
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 8
- 230000009467 reduction Effects 0.000 description 8
- 238000006722 reduction reaction Methods 0.000 description 8
- HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 8
- 235000019254 sodium formate Nutrition 0.000 description 8
- NOPPHGKRMIYOKI-GUBZILKMSA-N (3S)-1-[(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]propanoyl]diazinane-3-carboxylic acid Chemical compound CC(C)[C@H](N)C(=O)N[C@@H](C)C(=O)N1CCC[C@H](N1)C(O)=O NOPPHGKRMIYOKI-GUBZILKMSA-N 0.000 description 7
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 7
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 7
- 239000005695 Ammonium acetate Substances 0.000 description 7
- 241001465754 Metazoa Species 0.000 description 7
- 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 7
- 235000019257 ammonium acetate Nutrition 0.000 description 7
- 229940043376 ammonium acetate Drugs 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 7
- 125000005335 azido alkyl group Chemical group 0.000 description 7
- 239000003153 chemical reaction reagent Substances 0.000 description 7
- NXQGGXCHGDYOHB-UHFFFAOYSA-L cyclopenta-1,4-dien-1-yl(diphenyl)phosphane;dichloropalladium;iron(2+) Chemical compound [Fe+2].Cl[Pd]Cl.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 NXQGGXCHGDYOHB-UHFFFAOYSA-L 0.000 description 7
- 239000006260 foam Substances 0.000 description 7
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- 125000006588 heterocycloalkylene group Chemical group 0.000 description 7
- 239000012442 inert solvent Substances 0.000 description 7
- 238000000746 purification Methods 0.000 description 7
- 229960000329 ribavirin Drugs 0.000 description 7
- HZCAHMRRMINHDJ-DBRKOABJSA-N ribavirin Natural products O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1N=CN=C1 HZCAHMRRMINHDJ-DBRKOABJSA-N 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 238000006467 substitution reaction Methods 0.000 description 7
- 229910052717 sulfur Inorganic materials 0.000 description 7
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 description 6
- 241000400611 Eucalyptus deanei Species 0.000 description 6
- 108010050904 Interferons Proteins 0.000 description 6
- 102000014150 Interferons Human genes 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 6
- 125000002947 alkylene group Chemical group 0.000 description 6
- 235000019270 ammonium chloride Nutrition 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 150000001721 carbon Chemical group 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 150000002367 halogens Chemical class 0.000 description 6
- 150000002678 macrocyclic compounds Chemical class 0.000 description 6
- 238000006841 macrolactonization reaction Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000002798 polar solvent Substances 0.000 description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- 235000011181 potassium carbonates Nutrition 0.000 description 6
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Classifications
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- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
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- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
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Families Citing this family (81)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HK1211285A1 (en) | 2012-06-08 | 2016-05-20 | 吉利德科学公司 | Macrocyclic inhibitors of flaviviridae viruses |
| EP2859009B1 (en) | 2012-06-08 | 2017-10-18 | Gilead Sciences, Inc. | Macrocyclic inhibitors of flaviviridae viruses |
| AR091279A1 (es) * | 2012-06-08 | 2015-01-21 | Gilead Sciences Inc | Inhibidores macrociclicos de virus flaviviridae |
| EP3236972B1 (en) | 2014-12-26 | 2021-07-28 | Emory University | Anti-viral n4-hydroxycytidine derivatives |
| CR20170395A (es) | 2015-03-04 | 2017-11-07 | Gilead Sciences Inc | Compuestos moduladores de receptor de tipo toll |
| US20170008785A1 (en) * | 2015-07-07 | 2017-01-12 | Nch Corporation | System and Method for Treating Water with a Biological Based Biocide |
| AU2016312508A1 (en) | 2015-08-26 | 2018-02-15 | Gilead Sciences, Inc. | Deuterated toll-like receptor modulators |
| EP4491236A3 (en) | 2016-05-10 | 2025-04-02 | C4 Therapeutics, Inc. | Heterocyclic degronimers for target protein degradation |
| CN109790143A (zh) | 2016-05-10 | 2019-05-21 | C4医药公司 | 用于靶蛋白降解的胺连接的c3-戊二酰亚胺降解决定子体 |
| CN109641874A (zh) | 2016-05-10 | 2019-04-16 | C4医药公司 | 用于靶蛋白降解的c3-碳连接的戊二酰亚胺降解决定子体 |
| WO2017197036A1 (en) | 2016-05-10 | 2017-11-16 | C4 Therapeutics, Inc. | Spirocyclic degronimers for target protein degradation |
| BR102017010009A2 (pt) | 2016-05-27 | 2017-12-12 | Gilead Sciences, Inc. | Compounds for the treatment of hepatitis b virus infection |
| EP3463469B1 (en) | 2016-05-27 | 2023-12-13 | Gilead Sciences, Inc. | Combination of ledipasvir and sofosbuvir for use in the treatment of hepatitis b virus infections in humans |
| JOP20190024A1 (ar) | 2016-08-26 | 2019-02-19 | Gilead Sciences Inc | مركبات بيروليزين بها استبدال واستخداماتها |
| AU2017318601B2 (en) | 2016-09-02 | 2020-09-03 | Gilead Sciences, Inc. | Toll like receptor modulator compounds |
| US10640499B2 (en) | 2016-09-02 | 2020-05-05 | Gilead Sciences, Inc. | Toll like receptor modulator compounds |
| SG11201903042VA (en) | 2016-10-14 | 2019-05-30 | Precision Biosciences Inc | Engineered meganucleases specific for recognition sequences in the hepatitis b virus genome |
| CN110234645A (zh) | 2017-01-25 | 2019-09-13 | 巴斯夫欧洲公司 | 制备卞型酰胺的方法 |
| AR110768A1 (es) | 2017-01-31 | 2019-05-02 | Gilead Sciences Inc | Formas cristalinas de tenofovir alafenamida |
| JOP20180008A1 (ar) | 2017-02-02 | 2019-01-30 | Gilead Sciences Inc | مركبات لعلاج إصابة بعدوى فيروس الالتهاب الكبدي b |
| WO2018172250A1 (en) | 2017-03-21 | 2018-09-27 | Bayer Pharma Aktiengesellschaft | 2-methyl-quinazolines |
| JOP20180040A1 (ar) | 2017-04-20 | 2019-01-30 | Gilead Sciences Inc | مثبطات pd-1/pd-l1 |
| EP3641762A4 (en) | 2017-06-20 | 2021-03-10 | C4 Therapeutics, Inc. | N / O-LINKED DEGRONES AND DEGRONIMERS FOR PROTEIN DEGRADATION |
| CN109384727B (zh) * | 2017-08-10 | 2023-07-28 | 中国科学院上海药物研究所 | 酞嗪酮类化合物、其制备方法、药物组合物及用途 |
| WO2019040102A1 (en) | 2017-08-22 | 2019-02-28 | Gilead Sciences, Inc. | THERAPEUTIC HETEROCYCLIC COMPOUNDS |
| CN111372592A (zh) | 2017-12-07 | 2020-07-03 | 埃默里大学 | N4-羟基胞苷及衍生物和与其相关的抗病毒用途 |
| EP3724190B1 (en) | 2017-12-13 | 2022-07-06 | Lupin Limited | Substituted bicyclic heterocyclic compounds as prmt5 inhibitors |
| AU2018392212B9 (en) | 2017-12-20 | 2021-03-18 | Institute Of Organic Chemistry And Biochemistry Ascr, V.V.I. | 2'3' cyclic dinucleotides with phosphonate bond activating the STING adaptor protein |
| WO2019123340A1 (en) | 2017-12-20 | 2019-06-27 | Institute Of Organic Chemistry And Biochemistry Ascr, V.V.I. | 3'3' cyclic dinucleotides with phosphonate bond activating the sting adaptor protein |
| CN111712494A (zh) | 2018-02-13 | 2020-09-25 | 吉利德科学公司 | Pd-1/pd-l1抑制剂 |
| WO2019165374A1 (en) | 2018-02-26 | 2019-08-29 | Gilead Sciences, Inc. | Substituted pyrrolizine compounds as hbv replication inhibitors |
| EP3774883A1 (en) | 2018-04-05 | 2021-02-17 | Gilead Sciences, Inc. | Antibodies and fragments thereof that bind hepatitis b virus protein x |
| 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 |
| 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 |
| 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 |
| TW201945388A (zh) | 2018-04-12 | 2019-12-01 | 美商精密生物科學公司 | 對b型肝炎病毒基因體中之識別序列具有特異性之最佳化之經工程化巨核酸酶 |
| WO2019201848A1 (en) | 2018-04-18 | 2019-10-24 | Bayer Pharma Aktiengesellschaft | 2-methyl-aza-quinazolines |
| EP3781556B1 (en) | 2018-04-19 | 2025-06-18 | Gilead Sciences, Inc. | Pd-1/pd-l1 inhibitors |
| TW202014193A (zh) | 2018-05-03 | 2020-04-16 | 捷克科學院有機化學與生物化學研究所 | 包含碳環核苷酸之2’3’－環二核苷酸 |
| US11098027B2 (en) | 2018-07-06 | 2021-08-24 | Gilead Sciences, Inc. | Therapeutic heterocyclic compounds |
| AU2019297428C1 (en) | 2018-07-06 | 2023-03-23 | Gilead Sciences, Inc. | Therapeutic heterocyclic compounds |
| US10774071B2 (en) | 2018-07-13 | 2020-09-15 | Gilead Sciences, Inc. | PD-1/PD-L1 inhibitors |
| WO2020028097A1 (en) | 2018-08-01 | 2020-02-06 | Gilead Sciences, Inc. | Solid forms of (r)-11-(methoxymethyl)-12-(3-methoxypropoxy)-3,3-dimethyl-8-0x0-2,3,8,13b-tetrahydro-1h-pyrido[2,1-a]pyrrolo[1,2-c] phthalazine-7-c arboxylic acid |
| CA3117199C (en) | 2018-10-24 | 2024-03-19 | Gilead Sciences, Inc. | Pd-1/pd-l1 inhibitors |
| 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 |
| US11203591B2 (en) | 2018-10-31 | 2021-12-21 | Gilead Sciences, Inc. | Substituted 6-azabenzimidazole compounds |
| AU2020231115B2 (en) | 2019-03-07 | 2025-02-20 | Institute Of Organic Chemistry And Biochemistry Ascr, V.V.I. | 3'3'-cyclic dinucleotides and prodrugs thereof |
| KR102707808B1 (ko) | 2019-03-07 | 2024-09-19 | 인스티튜트 오브 오가닉 케미스트리 앤드 바이오케미스트리 에이에스 씨알 브이.브이.아이. | 2'3'-사이클릭 다이뉴클레오티드 및 이의 프로드럭 |
| 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 |
| 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 |
| 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 |
| US11453681B2 (en) | 2019-05-23 | 2022-09-27 | Gilead Sciences, Inc. | Substituted eneoxindoles and uses thereof |
| CA3140708A1 (en) | 2019-06-18 | 2020-12-24 | Helen Horton | Combination of hepatitis b virus (hbv) vaccines and pyridopyrimidine derivatives |
| MY202182A (en) | 2019-06-25 | 2024-04-15 | Gilead Sciences Inc | Flt3l-fc fusion proteins and methods of use |
| WO2021011891A1 (en) | 2019-07-18 | 2021-01-21 | Gilead Sciences, Inc. | Long-acting formulations of tenofovir alafenamide |
| WO2021034804A1 (en) | 2019-08-19 | 2021-02-25 | Gilead Sciences, Inc. | Pharmaceutical formulations of tenofovir alafenamide |
| KR20250040096A (ko) | 2019-09-30 | 2025-03-21 | 길리애드 사이언시즈, 인코포레이티드 | Hbv 백신 및 hbv를 치료하는 방법 |
| EP4055028A1 (en) * | 2019-11-04 | 2022-09-14 | Revolution Medicines, Inc. | Ras inhibitors |
| CN120988055A (zh) | 2019-11-04 | 2025-11-21 | 锐新医药公司 | Ras抑制剂 |
| KR20250133996A (ko) | 2019-11-04 | 2025-09-09 | 레볼루션 메디슨즈, 인크. | Ras 억제제 |
| DK4069729T3 (da) | 2019-12-06 | 2025-04-07 | Prec Biosciences Inc | Optimerede, modificerede meganukleaser med specificitet for en genkendelsessekvens i hepatitis b-virusgenomet |
| KR20220156884A (ko) | 2020-03-20 | 2022-11-28 | 길리애드 사이언시즈, 인코포레이티드 | 4'-c-치환된-2-할로-2'-데옥시아데노신 뉴클레오시드의 프로드러그 및 이의 제조 및 사용 방법 |
| WO2021198981A1 (en) | 2020-04-01 | 2021-10-07 | Janssen Biopharma, Inc. | Antiviral compounds and uses thereof |
| AU2021320236B2 (en) | 2020-08-07 | 2024-10-03 | Gilead Sciences, Inc. | Prodrugs of phosphonamide nucleotide analogues and their pharmaceutical use |
| CA3194067A1 (en) | 2020-09-15 | 2022-03-24 | Revolution Medicines, Inc. | Ras inhibitors |
| CA3195519A1 (en) | 2020-09-18 | 2022-03-24 | Bayer Aktiengesellschaft | Pyrido[2,3-d]pyrimidin-4-amines as sos1 inhibitors |
| 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 |
| EP4074317A1 (en) | 2021-04-14 | 2022-10-19 | Bayer AG | Phosphorus derivatives as novel sos1 inhibitors |
| CA3217920A1 (en) | 2021-05-05 | 2022-11-10 | Andreas BUCKL | Ras inhibitors for the treatment of cancer |
| EP4337223A1 (en) | 2021-05-13 | 2024-03-20 | Gilead Sciences, Inc. | Combination of a tlr8 modulating compound and anti-hbv sirna therapeutics |
| KR20240023629A (ko) | 2021-06-23 | 2024-02-22 | 길리애드 사이언시즈, 인코포레이티드 | 디아실글리세롤 키나제 조절 화합물 |
| EP4359389A1 (en) | 2021-06-23 | 2024-05-01 | Gilead Sciences, Inc. | Diacylglyercol kinase modulating compounds |
| US11999733B2 (en) | 2021-06-23 | 2024-06-04 | Gilead Sciences, Inc. | Diacylglycerol kinase modulating compounds |
| EP4359413A1 (en) | 2021-06-23 | 2024-05-01 | Gilead Sciences, Inc. | Diacylglyercol kinase modulating compounds |
| AR127308A1 (es) | 2021-10-08 | 2024-01-10 | Revolution Medicines Inc | Inhibidores ras |
| CN114634421A (zh) * | 2022-02-24 | 2022-06-17 | 济宁晟泰药业有限公司 | 一种达沙替尼中间体的制备方法 |
| CA3263179A1 (en) | 2022-07-29 | 2024-02-01 | Pfizer Inc. | Novel acc inhibitors |
| WO2025240243A1 (en) | 2024-05-13 | 2025-11-20 | Gilead Sciences, Inc. | Combination therapies with bulevirtide and an inhibitory nucleic acid targeting hepatitis b virus |
| WO2025240242A1 (en) | 2024-05-13 | 2025-11-20 | Gilead Sciences, Inc. | Combination therapies with ribavirin |
| WO2025240246A1 (en) | 2024-05-13 | 2025-11-20 | Gilead Sciences, Inc. | Combination therapies with ribavirin |
| WO2025240244A1 (en) | 2024-05-13 | 2025-11-20 | Gilead Sciences, Inc. | Combination therapies comprising bulevirtide and lonafarnib for use in the treatment of hepatitis d virus infection |
Family Cites Families (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR006514A1 (es) | 1995-07-04 | 1999-09-08 | Sandoz Ag | Un macrolido, sus usos, un proceso para producirlo, un aislado biologicamente puro capaz de producirlo, y una composicion farmaceutica quelo comprende |
| US6124453A (en) | 1995-07-04 | 2000-09-26 | Novartis Ag | Macrolides |
| DE10239042A1 (de) | 2002-08-21 | 2004-03-04 | Schering Ag | Makrozyclische Pyrimidine, deren Herstellung und Verwendung als Arzneimittel |
| US20050159345A1 (en) | 2002-10-29 | 2005-07-21 | Boehringer Ingelheim International Gmbh | Composition for the treatment of infection by Flaviviridae viruses |
| NZ564326A (en) | 2005-06-16 | 2010-01-29 | Cv Therapeutics Inc | Prodrugs of A2B adenosine receptor antagonists |
| BRPI0613142A2 (pt) | 2005-06-17 | 2010-12-21 | Novartis Ag | uso de sangliferina em hcv |
| EP2011786A1 (en) | 2007-07-05 | 2009-01-07 | Laboratorios del Dr. Esteve S.A. | Indane-amine derivatives, their preparation and use as medicaments |
| CL2008003384A1 (es) | 2007-11-14 | 2009-12-11 | Enanta Pharm Inc | Compuestos derivados de quinoxalina macrocíclica, inhibidores de serina proteasa; composicion farmaceutica que los comprende; y su uso en el tratamiento de la hepatitis c. |
| EP2241626B1 (en) | 2008-01-09 | 2016-01-06 | Konkuk University Industrial Cooperation Corp | Baculovirus-based vaccines |
| US20100080770A1 (en) | 2008-09-29 | 2010-04-01 | Bristol-Myers Squibb Company | Hepatitis C Virus Inhibitors |
| ES2429013T3 (es) * | 2008-12-23 | 2013-11-12 | Janssen Pharmaceuticals, Inc. | Procedimientos e intermedios para la preparación de un inhibidor macrocíclico de la proteasa de VHC |
| WO2011063233A1 (en) | 2009-11-23 | 2011-05-26 | Amgen Inc. | Amino heteroaryl compounds as beta-secretase modulators and methods of use |
| UY33183A (es) | 2010-01-15 | 2011-08-31 | Gilead Sciences Inc | Compuestos inhibidores de virus flaviviridae, composición farmaceutica que los contiene y su uso en la manufactura de un medicamento |
| WO2011090935A1 (en) | 2010-01-19 | 2011-07-28 | Merck Sharp & Dohme Corp. | PYRAZOLO[1,5-a]PYRIMIDINE COMPOUNDS AS mTOR INHIBITORS |
| WO2011098808A1 (en) * | 2010-02-09 | 2011-08-18 | Biotica Technology Limited | Sanglifehrin based compounds |
| GB201008123D0 (en) * | 2010-05-17 | 2010-06-30 | Biotica Tech Ltd | Novel compounds |
| EP2618665A4 (en) * | 2010-09-21 | 2014-08-20 | Merck Sharp & Dohme | HCV NS3 proteinase inhibitor |
| UY33775A (es) * | 2010-12-10 | 2012-07-31 | Gilead Sciences Inc | Inhibidores macrocíclicos de virus flaviviridae, composiciones farmacéuticas que los comprenden y sus usos |
| AR091279A1 (es) | 2012-06-08 | 2015-01-21 | Gilead Sciences Inc | Inhibidores macrociclicos de virus flaviviridae |
| EP2859009B1 (en) | 2012-06-08 | 2017-10-18 | Gilead Sciences, Inc. | Macrocyclic inhibitors of flaviviridae viruses |
| MX354014B (es) | 2012-06-08 | 2018-02-08 | Glenmark Pharmaceuticals Sa | Amidas de compuestos de 2-amino-4-ariltiazol y sus sales. |
| HK1211285A1 (en) | 2012-06-08 | 2016-05-20 | 吉利德科学公司 | Macrocyclic inhibitors of flaviviridae viruses |
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| PT2861604T (pt) | 2017-05-05 |
| CA2875692A1 (en) | 2013-12-12 |
| PL2861604T3 (pl) | 2017-08-31 |
| WO2013185103A1 (en) | 2013-12-12 |
| CN104703991A (zh) | 2015-06-10 |
| HK1211285A1 (en) | 2016-05-20 |
| ES2624223T3 (es) | 2017-07-13 |
| EA201492209A1 (ru) | 2015-05-29 |
| NZ703040A (en) | 2016-11-25 |
| US9145441B2 (en) | 2015-09-29 |
| CN104703991B (zh) | 2018-03-23 |
| EP2861604A1 (en) | 2015-04-22 |
| HK1209730A1 (en) | 2016-04-08 |
| EP2861604B1 (en) | 2017-03-01 |
| SG11201408047XA (en) | 2015-01-29 |
| US20150344521A1 (en) | 2015-12-03 |
| JP6209601B2 (ja) | 2017-10-04 |
| KR20150040265A (ko) | 2015-04-14 |
| BR112014030630A2 (pt) | 2017-06-27 |
| SI2861604T1 (sl) | 2017-05-31 |
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