HUE030175T2 - Arginine salt of TLR7 agonist - Google Patents
Arginine salt of TLR7 agonist Download PDFInfo
- Publication number
- HUE030175T2 HUE030175T2 HUE13708142A HUE13708142A HUE030175T2 HU E030175 T2 HUE030175 T2 HU E030175T2 HU E13708142 A HUE13708142 A HU E13708142A HU E13708142 A HUE13708142 A HU E13708142A HU E030175 T2 HUE030175 T2 HU E030175T2
- Authority
- HU
- Hungary
- Prior art keywords
- salt
- compound
- arginine
- formula
- immunogen
- Prior art date
Links
- 229940124615 TLR 7 agonist Drugs 0.000 title 1
- 125000000637 arginyl group Chemical class N[C@@H](CCCNC(N)=N)C(=O)* 0.000 title 1
- 239000000203 mixture Substances 0.000 claims description 111
- 150000003839 salts Chemical class 0.000 claims description 104
- 230000002163 immunogen Effects 0.000 claims description 100
- 238000000034 method Methods 0.000 claims description 28
- 239000007787 solid Substances 0.000 claims description 21
- 230000008569 process Effects 0.000 claims description 14
- -1 salt salt Chemical class 0.000 claims description 13
- 238000002560 therapeutic procedure Methods 0.000 claims description 11
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
- 201000010099 disease Diseases 0.000 claims description 7
- 230000004044 response Effects 0.000 claims description 4
- 230000018044 dehydration Effects 0.000 claims 2
- 238000006297 dehydration reaction Methods 0.000 claims 2
- 230000000422 nocturnal effect Effects 0.000 claims 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims 1
- 238000011033 desalting Methods 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 122
- 150000001483 arginine derivatives Chemical class 0.000 description 104
- 239000000427 antigen Substances 0.000 description 58
- 102000036639 antigens Human genes 0.000 description 57
- 108091007433 antigens Proteins 0.000 description 57
- 239000002671 adjuvant Substances 0.000 description 50
- 229910052751 metal Inorganic materials 0.000 description 47
- 239000002184 metal Substances 0.000 description 47
- 230000028993 immune response Effects 0.000 description 40
- 239000012458 free base Substances 0.000 description 33
- 229920001184 polypeptide Polymers 0.000 description 33
- 108090000765 processed proteins & peptides Proteins 0.000 description 33
- 102000004196 processed proteins & peptides Human genes 0.000 description 33
- 229960005486 vaccine Drugs 0.000 description 31
- 229910021502 aluminium hydroxide Inorganic materials 0.000 description 27
- 239000000243 solution Substances 0.000 description 27
- 238000001179 sorption measurement Methods 0.000 description 27
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 26
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 26
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 26
- 239000008194 pharmaceutical composition Substances 0.000 description 26
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 23
- 238000004519 manufacturing process Methods 0.000 description 22
- 239000004475 Arginine Substances 0.000 description 21
- 125000002059 L-arginyl group Chemical class O=C([*])[C@](N([H])[H])([H])C([H])([H])C([H])([H])C([H])([H])N([H])C(=N[H])N([H])[H] 0.000 description 21
- 235000009697 arginine Nutrition 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 21
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
- 159000000013 aluminium salts Chemical class 0.000 description 19
- 150000001720 carbohydrates Chemical class 0.000 description 19
- 239000000872 buffer Substances 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- ILRRQNADMUWWFW-UHFFFAOYSA-K aluminium phosphate Chemical compound O1[Al]2OP1(=O)O2 ILRRQNADMUWWFW-UHFFFAOYSA-K 0.000 description 16
- 229940001007 aluminium phosphate Drugs 0.000 description 15
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
- 229910000329 aluminium sulfate Inorganic materials 0.000 description 13
- 238000002156 mixing Methods 0.000 description 13
- 102000002689 Toll-like receptor Human genes 0.000 description 12
- 108020000411 Toll-like receptor Proteins 0.000 description 12
- 201000005702 Pertussis Diseases 0.000 description 11
- 125000005605 benzo group Chemical group 0.000 description 11
- 210000004027 cell Anatomy 0.000 description 11
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 11
- 235000019439 ethyl acetate Nutrition 0.000 description 10
- 230000000091 immunopotentiator Effects 0.000 description 10
- 238000000634 powder X-ray diffraction Methods 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 241000700605 Viruses Species 0.000 description 9
- 229960003983 diphtheria toxoid Drugs 0.000 description 9
- 239000003814 drug Substances 0.000 description 9
- 229960000814 tetanus toxoid Drugs 0.000 description 9
- 241000991587 Enterovirus C Species 0.000 description 8
- 229910052782 aluminium Inorganic materials 0.000 description 8
- 239000004411 aluminium Substances 0.000 description 8
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 8
- 238000001556 precipitation Methods 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 7
- 241000588650 Neisseria meningitidis Species 0.000 description 7
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 7
- 230000015556 catabolic process Effects 0.000 description 7
- 238000006731 degradation reaction Methods 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 238000009472 formulation Methods 0.000 description 7
- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 description 7
- 235000019260 propionic acid Nutrition 0.000 description 7
- HNSNJSFETJFQJF-UHFFFAOYSA-N 1-ethynyl-4-(methoxymethoxy)-2-methylbenzene Chemical compound COCOC1=CC=C(C#C)C(C)=C1 HNSNJSFETJFQJF-UHFFFAOYSA-N 0.000 description 6
- JBTQFASNIMCBCD-UHFFFAOYSA-N 3-chloro-5-[2-[4-(methoxymethoxy)-2-methylphenyl]ethynyl]pyridine-2-carbonitrile Chemical compound CC1=CC(OCOC)=CC=C1C#CC1=CN=C(C#N)C(Cl)=C1 JBTQFASNIMCBCD-UHFFFAOYSA-N 0.000 description 6
- FWMNVWWHGCHHJJ-SKKKGAJSSA-N 4-amino-1-[(2r)-6-amino-2-[[(2r)-2-[[(2r)-2-[[(2r)-2-amino-3-phenylpropanoyl]amino]-3-phenylpropanoyl]amino]-4-methylpentanoyl]amino]hexanoyl]piperidine-4-carboxylic acid Chemical compound C([C@H](C(=O)N[C@H](CC(C)C)C(=O)N[C@H](CCCCN)C(=O)N1CCC(N)(CC1)C(O)=O)NC(=O)[C@H](N)CC=1C=CC=CC=1)C1=CC=CC=C1 FWMNVWWHGCHHJJ-SKKKGAJSSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 241000894006 Bacteria Species 0.000 description 6
- 241000700721 Hepatitis B virus Species 0.000 description 6
- ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical compound OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 description 6
- 241000725643 Respiratory syncytial virus Species 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000000556 agonist Substances 0.000 description 6
- 150000003863 ammonium salts Chemical class 0.000 description 6
- 230000001580 bacterial effect Effects 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 6
- QPZIMHZHRZMOMD-VQHVLOKHSA-N ethyl (e)-3-[4-chloro-3-[(2-methylpropan-2-yl)oxycarbonylamino]phenyl]prop-2-enoate Chemical compound CCOC(=O)\C=C\C1=CC=C(Cl)C(NC(=O)OC(C)(C)C)=C1 QPZIMHZHRZMOMD-VQHVLOKHSA-N 0.000 description 6
- QQLIOZCPDFUIKW-UHFFFAOYSA-N ethyl 3-[3-[(2-methylpropan-2-yl)oxycarbonylamino]-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]propanoate Chemical compound CC(C)(C)OC(=O)NC1=CC(CCC(=O)OCC)=CC=C1B1OC(C)(C)C(C)(C)O1 QQLIOZCPDFUIKW-UHFFFAOYSA-N 0.000 description 6
- NIDKCCJZUOZEQN-UHFFFAOYSA-N ethyl 3-[4-chloro-3-[(2-methylpropan-2-yl)oxycarbonylamino]phenyl]propanoate Chemical compound CCOC(=O)CCC1=CC=C(Cl)C(NC(=O)OC(C)(C)C)=C1 NIDKCCJZUOZEQN-UHFFFAOYSA-N 0.000 description 6
- WFQUKHXDYBTQMF-UHFFFAOYSA-N ethyl 3-[5-amino-2-[2-[4-(methoxymethoxy)-2-methylphenyl]ethyl]benzo[f][1,7]naphthyridin-8-yl]propanoate Chemical compound C=1C(CCC(=O)OCC)=CC=C(C2=C3)C=1N=C(N)C2=NC=C3CCC1=CC=C(OCOC)C=C1C WFQUKHXDYBTQMF-UHFFFAOYSA-N 0.000 description 6
- 229940093499 ethyl acetate Drugs 0.000 description 6
- 238000002347 injection Methods 0.000 description 6
- 239000007924 injection Substances 0.000 description 6
- 239000000377 silicon dioxide Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 230000009885 systemic effect Effects 0.000 description 6
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 6
- BZPXVNBSNXWGCX-UHFFFAOYSA-N 1-(2-diethoxyphosphorylethoxy)-2-(2-iodoethoxy)ethane Chemical compound CCOP(=O)(OCC)CCOCCOCCI BZPXVNBSNXWGCX-UHFFFAOYSA-N 0.000 description 5
- BSJSWKNICXZUDB-UHFFFAOYSA-N 1-bromo-4-(methoxymethoxy)-2-methylbenzene Chemical compound COCOC1=CC=C(Br)C(C)=C1 BSJSWKNICXZUDB-UHFFFAOYSA-N 0.000 description 5
- 102100027723 Endogenous retrovirus group K member 6 Rec protein Human genes 0.000 description 5
- 101710121417 Envelope glycoprotein Proteins 0.000 description 5
- 241000606768 Haemophilus influenzae Species 0.000 description 5
- 229930064664 L-arginine Natural products 0.000 description 5
- 235000014852 L-arginine Nutrition 0.000 description 5
- 206010028980 Neoplasm Diseases 0.000 description 5
- 230000000274 adsorptive effect Effects 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 239000013058 crude material Substances 0.000 description 5
- VRKNDNRPRSPIMF-UHFFFAOYSA-N ethyl 3-[5-amino-2-[2-[4-(methoxymethoxy)-2-methylphenyl]ethynyl]benzo[f][1,7]naphthyridin-8-yl]propanoate Chemical compound C=1C(CCC(=O)OCC)=CC=C(C2=C3)C=1N=C(N)C2=NC=C3C#CC1=CC=C(OCOC)C=C1C VRKNDNRPRSPIMF-UHFFFAOYSA-N 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 238000002649 immunization Methods 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000012528 membrane Substances 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- 108010021711 pertactin Proteins 0.000 description 5
- 108090000623 proteins and genes Proteins 0.000 description 5
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 4
- 241000588832 Bordetella pertussis Species 0.000 description 4
- 102000014914 Carrier Proteins Human genes 0.000 description 4
- 108010078791 Carrier Proteins Proteins 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 4
- 229910019142 PO4 Inorganic materials 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 4
- 239000007983 Tris buffer Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 238000000113 differential scanning calorimetry Methods 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- QKYXPXCSGDEJOB-UHFFFAOYSA-N ethyl 3-[5-amino-2-[2-(4-hydroxy-2-methylphenyl)ethyl]benzo[f][1,7]naphthyridin-8-yl]propanoate Chemical compound C=1C(CCC(=O)OCC)=CC=C(C2=C3)C=1N=C(N)C2=NC=C3CCC1=CC=C(O)C=C1C QKYXPXCSGDEJOB-UHFFFAOYSA-N 0.000 description 4
- 238000001727 in vivo Methods 0.000 description 4
- 238000010255 intramuscular injection Methods 0.000 description 4
- 239000007927 intramuscular injection Substances 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 244000052769 pathogen Species 0.000 description 4
- 239000010452 phosphate Substances 0.000 description 4
- 235000021317 phosphate Nutrition 0.000 description 4
- 239000008363 phosphate buffer Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 210000002966 serum Anatomy 0.000 description 4
- 238000004659 sterilization and disinfection Methods 0.000 description 4
- SPWXXIWXFICVFJ-UHFFFAOYSA-N triethyl-[2-[4-(methoxymethoxy)-2-methylphenyl]ethynyl]silane Chemical compound CC[Si](CC)(CC)C#CC1=CC=C(OCOC)C=C1C SPWXXIWXFICVFJ-UHFFFAOYSA-N 0.000 description 4
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 4
- 241000712461 unidentified influenza virus Species 0.000 description 4
- 230000003612 virological effect Effects 0.000 description 4
- FEMXQTNILSJYNG-UHFFFAOYSA-N 3-[5-amino-2-[2-[2-methyl-4-[2-[2-(2-phosphonoethoxy)ethoxy]ethoxy]phenyl]ethyl]benzo[f][1,7]naphthyridin-8-yl]propanoic acid Chemical compound CC1=CC(OCCOCCOCCP(O)(O)=O)=CC=C1CCC1=CN=C(C(N)=NC=2C3=CC=C(CCC(O)=O)C=2)C3=C1 FEMXQTNILSJYNG-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
- 208000023275 Autoimmune disease Diseases 0.000 description 3
- 108090000695 Cytokines Proteins 0.000 description 3
- 102000004127 Cytokines Human genes 0.000 description 3
- ODKSFYDXXFIFQN-SCSAIBSYSA-N D-arginine Chemical compound OC(=O)[C@H](N)CCCNC(N)=N ODKSFYDXXFIFQN-SCSAIBSYSA-N 0.000 description 3
- 229930028154 D-arginine Natural products 0.000 description 3
- 101710186862 Factor H binding protein Proteins 0.000 description 3
- 108090000288 Glycoproteins Proteins 0.000 description 3
- 102000003886 Glycoproteins Human genes 0.000 description 3
- 241000124008 Mammalia Species 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001450 anions Chemical class 0.000 description 3
- 230000005875 antibody response Effects 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- 239000012267 brine Substances 0.000 description 3
- 239000001506 calcium phosphate Substances 0.000 description 3
- 229910000389 calcium phosphate Inorganic materials 0.000 description 3
- 235000011010 calcium phosphates Nutrition 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 239000003446 ligand Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 102000007863 pattern recognition receptors Human genes 0.000 description 3
- 108010089193 pattern recognition receptors Proteins 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 3
- 229910000160 potassium phosphate Inorganic materials 0.000 description 3
- 235000011009 potassium phosphates Nutrition 0.000 description 3
- 230000000770 proinflammatory effect Effects 0.000 description 3
- 230000001681 protective effect Effects 0.000 description 3
- 235000018102 proteins Nutrition 0.000 description 3
- 102000004169 proteins and genes Human genes 0.000 description 3
- 238000004007 reversed phase HPLC Methods 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 230000001954 sterilising effect Effects 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 238000002411 thermogravimetry Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 2
- ATUOLSDAAPMVJJ-UHFFFAOYSA-N 3,5-dichloropyridine-2-carbonitrile Chemical compound ClC1=CN=C(C#N)C(Cl)=C1 ATUOLSDAAPMVJJ-UHFFFAOYSA-N 0.000 description 2
- GPOQODYGMUTOQL-UHFFFAOYSA-N 4-bromo-3-methylphenol Chemical compound CC1=CC(O)=CC=C1Br GPOQODYGMUTOQL-UHFFFAOYSA-N 0.000 description 2
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- 208000035143 Bacterial infection Diseases 0.000 description 2
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- 101710154643 Filamentous hemagglutinin Proteins 0.000 description 2
- 101710114810 Glycoprotein Proteins 0.000 description 2
- 101710154606 Hemagglutinin Proteins 0.000 description 2
- 241000709721 Hepatovirus A Species 0.000 description 2
- 241000238631 Hexapoda Species 0.000 description 2
- 101000669402 Homo sapiens Toll-like receptor 7 Proteins 0.000 description 2
- 241000725303 Human immunodeficiency virus Species 0.000 description 2
- 241000341655 Human papillomavirus type 16 Species 0.000 description 2
- 241000709701 Human poliovirus 1 Species 0.000 description 2
- 241000709704 Human poliovirus 2 Species 0.000 description 2
- 241000709727 Human poliovirus 3 Species 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 101150075239 L1 gene Proteins 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- 241000712079 Measles morbillivirus Species 0.000 description 2
- 241000711386 Mumps virus Species 0.000 description 2
- 208000031888 Mycoses Diseases 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 101710093908 Outer capsid protein VP4 Proteins 0.000 description 2
- 101710135467 Outer capsid protein sigma-1 Proteins 0.000 description 2
- 101710116435 Outer membrane protein Proteins 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 208000030852 Parasitic disease Diseases 0.000 description 2
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical group OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 2
- 101100388690 Plasmodium falciparum (isolate K1 / Thailand) MEF-1 gene Proteins 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- 101710176177 Protein A56 Proteins 0.000 description 2
- 241000711798 Rabies lyssavirus Species 0.000 description 2
- 241000710799 Rubella virus Species 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 101710167605 Spike glycoprotein Proteins 0.000 description 2
- 241000193985 Streptococcus agalactiae Species 0.000 description 2
- 238000003917 TEM image Methods 0.000 description 2
- 240000006909 Tilia x europaea Species 0.000 description 2
- 235000011941 Tilia x europaea Nutrition 0.000 description 2
- 101800001690 Transmembrane protein gp41 Proteins 0.000 description 2
- 208000018756 Variant Creutzfeldt-Jakob disease Diseases 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229940037003 alum Drugs 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 208000022362 bacterial infectious disease Diseases 0.000 description 2
- 208000005881 bovine spongiform encephalopathy Diseases 0.000 description 2
- IYYIVELXUANFED-UHFFFAOYSA-N bromo(trimethyl)silane Chemical compound C[Si](C)(C)Br IYYIVELXUANFED-UHFFFAOYSA-N 0.000 description 2
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 2
- ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 description 2
- 210000004443 dendritic cell Anatomy 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 208000035475 disorder Diseases 0.000 description 2
- 235000013601 eggs Nutrition 0.000 description 2
- ZXDDITJXZPTHFE-BQYQJAHWSA-N ethyl (e)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)prop-2-enoate Chemical compound CCOC(=O)\C=C\B1OC(C)(C)C(C)(C)O1 ZXDDITJXZPTHFE-BQYQJAHWSA-N 0.000 description 2
- 230000003311 flocculating effect Effects 0.000 description 2
- 108020001507 fusion proteins Proteins 0.000 description 2
- 102000037865 fusion proteins Human genes 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000000185 hemagglutinin Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 229940031551 inactivated vaccine Drugs 0.000 description 2
- 206010022000 influenza Diseases 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 239000004571 lime Substances 0.000 description 2
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 150000004682 monohydrates Chemical group 0.000 description 2
- 210000003205 muscle Anatomy 0.000 description 2
- 238000002204 nitrogen-15 nuclear magnetic resonance spectrum Methods 0.000 description 2
- UQPUONNXJVWHRM-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 UQPUONNXJVWHRM-UHFFFAOYSA-N 0.000 description 2
- 230000001717 pathogenic effect Effects 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 229960005323 phenoxyethanol Drugs 0.000 description 2
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000008174 sterile solution Substances 0.000 description 2
- QPLKXDQLRIQYIA-UHFFFAOYSA-N tert-butyl n-(5-bromo-2-chlorophenyl)carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC(Br)=CC=C1Cl QPLKXDQLRIQYIA-UHFFFAOYSA-N 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 2
- RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 2
- 229960004906 thiomersal Drugs 0.000 description 2
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 2
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 2
- APJYDQYYACXCRM-UHFFFAOYSA-N tryptamine Chemical compound C1=CC=C2C(CCN)=CNC2=C1 APJYDQYYACXCRM-UHFFFAOYSA-N 0.000 description 2
- 210000002845 virion Anatomy 0.000 description 2
- 210000005253 yeast cell Anatomy 0.000 description 2
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 1
- FYGDTMLNYKFZSV-URKRLVJHSA-N (2s,3r,4s,5s,6r)-2-[(2r,4r,5r,6s)-4,5-dihydroxy-2-(hydroxymethyl)-6-[(2r,4r,5r,6s)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1[C@@H](CO)O[C@@H](OC2[C@H](O[C@H](O)[C@H](O)[C@H]2O)CO)[C@H](O)[C@H]1O FYGDTMLNYKFZSV-URKRLVJHSA-N 0.000 description 1
- SSOORFWOBGFTHL-OTEJMHTDSA-N (4S)-5-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-6-amino-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[2-[(2S)-2-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-6-amino-1-[[(2S)-1-[[(2S)-1-[[(2S,3S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-6-amino-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-5-amino-1-[[(2S)-1-[[(2S)-1-[[(2S)-6-amino-1-[[(2S)-6-amino-1-[[(2S)-1-[[(2S)-1-[[(2S)-5-amino-1-[[(2S)-5-carbamimidamido-1-[[(2S)-5-carbamimidamido-1-[[(1S)-4-carbamimidamido-1-carboxybutyl]amino]-1-oxopentan-2-yl]amino]-1-oxopentan-2-yl]amino]-1,5-dioxopentan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-1-oxohexan-2-yl]amino]-1-oxohexan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-1,5-dioxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-1-oxopropan-2-yl]amino]-1-oxohexan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-1-oxohexan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-1-oxopropan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]carbamoyl]pyrrolidin-1-yl]-2-oxoethyl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-1-oxohexan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-3-(1H-imidazol-4-yl)-1-oxopropan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-4-[[(2S)-2-[[(2S)-2-[[(2S)-2,6-diaminohexanoyl]amino]-3-methylbutanoyl]amino]propanoyl]amino]-5-oxopentanoic acid Chemical compound CC[C@H](C)[C@H](NC(=O)[C@@H](NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCCCN)NC(=O)[C@@H](NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@@H]1CCCN1C(=O)CNC(=O)[C@H](Cc1c[nH]c2ccccc12)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](Cc1ccccc1)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCCCN)NC(=O)[C@@H](NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](Cc1ccccc1)NC(=O)[C@H](Cc1c[nH]cn1)NC(=O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@@H](NC(=O)[C@@H](N)CCCCN)C(C)C)C(C)C)C(C)C)C(C)C)C(C)C)C(C)C)C(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C)C(=O)N[C@@H](CO)C(=O)N[C@@H](CO)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O SSOORFWOBGFTHL-OTEJMHTDSA-N 0.000 description 1
- BCAGFJXMCZSAHD-UHFFFAOYSA-N 1,2-bis(2-iodoethoxy)ethane Chemical compound ICCOCCOCCI BCAGFJXMCZSAHD-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- LKKMLIBUAXYLOY-UHFFFAOYSA-N 3-Amino-1-methyl-5H-pyrido[4,3-b]indole Chemical compound N1C2=CC=CC=C2C2=C1C=C(N)N=C2C LKKMLIBUAXYLOY-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 208000024827 Alzheimer disease Diseases 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 229920002498 Beta-glucan Polymers 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- 206010006187 Breast cancer Diseases 0.000 description 1
- 208000026310 Breast neoplasm Diseases 0.000 description 1
- 102100021943 C-C motif chemokine 2 Human genes 0.000 description 1
- 101710155857 C-C motif chemokine 2 Proteins 0.000 description 1
- 108010071134 CRM197 (non-toxic variant of diphtheria toxin) Proteins 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 241000222120 Candida <Saccharomycetales> Species 0.000 description 1
- 241000222122 Candida albicans Species 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 description 1
- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 description 1
- 108090000565 Capsid Proteins Proteins 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 102100023321 Ceruloplasmin Human genes 0.000 description 1
- 241000606161 Chlamydia Species 0.000 description 1
- 241001647372 Chlamydia pneumoniae Species 0.000 description 1
- 241000606153 Chlamydia trachomatis Species 0.000 description 1
- XJUZRXYOEPSWMB-UHFFFAOYSA-N Chloromethyl methyl ether Chemical compound COCCl XJUZRXYOEPSWMB-UHFFFAOYSA-N 0.000 description 1
- 241000193449 Clostridium tetani Species 0.000 description 1
- 241000711573 Coronaviridae Species 0.000 description 1
- 241000186227 Corynebacterium diphtheriae Species 0.000 description 1
- 241000701022 Cytomegalovirus Species 0.000 description 1
- 102100037840 Dehydrogenase/reductase SDR family member 2, mitochondrial Human genes 0.000 description 1
- 206010012335 Dependence Diseases 0.000 description 1
- 241000255581 Drosophila <fruit fly, genus> Species 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 241001295925 Gegenes Species 0.000 description 1
- 229920001503 Glucan Polymers 0.000 description 1
- 108010068370 Glutens Proteins 0.000 description 1
- JMBQKKAJIKAWKF-UHFFFAOYSA-N Glutethimide Chemical compound C=1C=CC=CC=1C1(CC)CCC(=O)NC1=O JMBQKKAJIKAWKF-UHFFFAOYSA-N 0.000 description 1
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical group NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 1
- 208000031886 HIV Infections Diseases 0.000 description 1
- 108010006464 Hemolysin Proteins Proteins 0.000 description 1
- 241000711549 Hepacivirus C Species 0.000 description 1
- 241000724675 Hepatitis E virus Species 0.000 description 1
- 101000578784 Homo sapiens Melanoma antigen recognized by T-cells 1 Proteins 0.000 description 1
- 101100151951 Homo sapiens SARS1 gene Proteins 0.000 description 1
- 241000713772 Human immunodeficiency virus 1 Species 0.000 description 1
- 241000713340 Human immunodeficiency virus 2 Species 0.000 description 1
- 241000701806 Human papillomavirus Species 0.000 description 1
- 241000701828 Human papillomavirus type 11 Species 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 241000712431 Influenza A virus Species 0.000 description 1
- 102100037850 Interferon gamma Human genes 0.000 description 1
- 108010074328 Interferon-gamma Proteins 0.000 description 1
- 102000003814 Interleukin-10 Human genes 0.000 description 1
- 108090000174 Interleukin-10 Proteins 0.000 description 1
- 102000013462 Interleukin-12 Human genes 0.000 description 1
- 108010065805 Interleukin-12 Proteins 0.000 description 1
- 102100031413 L-dopachrome tautomerase Human genes 0.000 description 1
- 101710093778 L-dopachrome tautomerase Proteins 0.000 description 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 description 1
- VAYOSLLFUXYJDT-RDTXWAMCSA-N Lysergic acid diethylamide Chemical compound C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N(CC)CC)C2)=C3C2=CNC3=C1 VAYOSLLFUXYJDT-RDTXWAMCSA-N 0.000 description 1
- 102100022430 Melanocyte protein PMEL Human genes 0.000 description 1
- 102100028389 Melanoma antigen recognized by T-cells 1 Human genes 0.000 description 1
- JEYCTXHKTXCGPB-UHFFFAOYSA-N Methaqualone Chemical compound CC1=CC=CC=C1N1C(=O)C2=CC=CC=C2N=C1C JEYCTXHKTXCGPB-UHFFFAOYSA-N 0.000 description 1
- SIDLZWOQUZRBRU-UHFFFAOYSA-N Methyprylon Chemical compound CCC1(CC)C(=O)NCC(C)C1=O SIDLZWOQUZRBRU-UHFFFAOYSA-N 0.000 description 1
- 241000588655 Moraxella catarrhalis Species 0.000 description 1
- 101100476480 Mus musculus S100a8 gene Proteins 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N Pd(PPh3)4 Substances [Pd].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.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 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 108010081690 Pertussis Toxin Proteins 0.000 description 1
- 241000288906 Primates Species 0.000 description 1
- 206010060862 Prostate cancer Diseases 0.000 description 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 description 1
- 101710188053 Protein D Proteins 0.000 description 1
- QVDSEJDULKLHCG-UHFFFAOYSA-N Psilocybine Natural products C1=CC(OP(O)(O)=O)=C2C(CCN(C)C)=CNC2=C1 QVDSEJDULKLHCG-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 101710132893 Resolvase Proteins 0.000 description 1
- 241000315672 SARS coronavirus Species 0.000 description 1
- 101710173694 Short transient receptor potential channel 2 Proteins 0.000 description 1
- 241000256248 Spodoptera Species 0.000 description 1
- 241000256251 Spodoptera frugiperda Species 0.000 description 1
- 241000191940 Staphylococcus Species 0.000 description 1
- 241000191963 Staphylococcus epidermidis Species 0.000 description 1
- 241000194017 Streptococcus Species 0.000 description 1
- 241000193996 Streptococcus pyogenes Species 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 101800001271 Surface protein Proteins 0.000 description 1
- 241001080024 Telles Species 0.000 description 1
- 102100039390 Toll-like receptor 7 Human genes 0.000 description 1
- 108060008682 Tumor Necrosis Factor Proteins 0.000 description 1
- 102100040247 Tumor necrosis factor Human genes 0.000 description 1
- 102000003425 Tyrosinase Human genes 0.000 description 1
- 108060008724 Tyrosinase Proteins 0.000 description 1
- 241000251539 Vertebrata <Metazoa> Species 0.000 description 1
- 229940022663 acetate Drugs 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000000240 adjuvant effect Effects 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000001345 alkine derivatives Chemical class 0.000 description 1
- 150000001370 alpha-amino acid derivatives Chemical class 0.000 description 1
- 235000008206 alpha-amino acids Nutrition 0.000 description 1
- 150000001399 aluminium compounds Chemical class 0.000 description 1
- 235000001014 amino acid Nutrition 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 229940077746 antacid containing aluminium compound Drugs 0.000 description 1
- 230000001078 anti-cholinergic effect Effects 0.000 description 1
- 230000001948 anti-meningococcal effect Effects 0.000 description 1
- 230000000935 anti-streptococcal effect Effects 0.000 description 1
- 239000000164 antipsychotic agent Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 230000001363 autoimmune Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- SWJXWSAKHXBQSY-UHFFFAOYSA-N benzo(c)cinnoline Chemical group C1=CC=C2C3=CC=CC=C3N=NC2=C1 SWJXWSAKHXBQSY-UHFFFAOYSA-N 0.000 description 1
- 229940049706 benzodiazepine Drugs 0.000 description 1
- 150000001557 benzodiazepines Chemical class 0.000 description 1
- IPWKHHSGDUIRAH-UHFFFAOYSA-N bis(pinacolato)diboron Chemical compound O1C(C)(C)C(C)(C)OB1B1OC(C)(C)C(C)(C)O1 IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 description 1
- 239000000337 buffer salt Substances 0.000 description 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- RNFNDJAIBTYOQL-UHFFFAOYSA-N chloral hydrate Chemical compound OC(O)C(Cl)(Cl)Cl RNFNDJAIBTYOQL-UHFFFAOYSA-N 0.000 description 1
- 229960002327 chloral hydrate Drugs 0.000 description 1
- 239000007979 citrate buffer Substances 0.000 description 1
- 229960003920 cocaine Drugs 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000007933 dermal patch Substances 0.000 description 1
- 238000003795 desorption Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- MKYNHKOAYQRSBD-UHFFFAOYSA-N dioxouranium;nitric acid Chemical compound O=[U]=O.O[N+]([O-])=O.O[N+]([O-])=O MKYNHKOAYQRSBD-UHFFFAOYSA-N 0.000 description 1
- 229960005097 diphtheria vaccines Drugs 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 229910000397 disodium phosphate Inorganic materials 0.000 description 1
- 235000019800 disodium phosphate Nutrition 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 210000002889 endothelial cell Anatomy 0.000 description 1
- 239000002158 endotoxin Substances 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 210000002950 fibroblast Anatomy 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 235000021312 gluten Nutrition 0.000 description 1
- 229960002972 glutethimide Drugs 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 239000003228 hemolysin Substances 0.000 description 1
- 108010037896 heparin-binding hemagglutinin Proteins 0.000 description 1
- 208000006454 hepatitis Diseases 0.000 description 1
- 231100000283 hepatitis Toxicity 0.000 description 1
- 210000003630 histaminocyte Anatomy 0.000 description 1
- 229930186900 holotoxin Natural products 0.000 description 1
- 102000045715 human TLR7 Human genes 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 210000002865 immune cell Anatomy 0.000 description 1
- 230000001900 immune effect Effects 0.000 description 1
- 210000000987 immune system Anatomy 0.000 description 1
- 230000005847 immunogenicity Effects 0.000 description 1
- 230000001024 immunotherapeutic effect Effects 0.000 description 1
- 238000009169 immunotherapy Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000002458 infectious effect Effects 0.000 description 1
- 208000037797 influenza A Diseases 0.000 description 1
- 208000037798 influenza B Diseases 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 210000005007 innate immune system Anatomy 0.000 description 1
- 229910052816 inorganic phosphate Inorganic materials 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000006193 liquid solution Substances 0.000 description 1
- 239000006194 liquid suspension Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 201000005202 lung cancer Diseases 0.000 description 1
- 208000020816 lung neoplasm Diseases 0.000 description 1
- 229950002454 lysergide Drugs 0.000 description 1
- 210000002540 macrophage Anatomy 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 201000001441 melanoma Diseases 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 229940057952 methanol Drugs 0.000 description 1
- 229960002803 methaqualone Drugs 0.000 description 1
- 229960000316 methyprylon Drugs 0.000 description 1
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
- 235000019796 monopotassium phosphate Nutrition 0.000 description 1
- 230000001459 mortal effect Effects 0.000 description 1
- 238000002703 mutagenesis Methods 0.000 description 1
- 231100000350 mutagenesis Toxicity 0.000 description 1
- 230000035772 mutation Effects 0.000 description 1
- 210000000440 neutrophil Anatomy 0.000 description 1
- 229960002715 nicotine Drugs 0.000 description 1
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 1
- 244000309711 non-enveloped viruses Species 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 229940127240 opiate Drugs 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
- 229940066827 pertussis vaccine Drugs 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229950010883 phencyclidine Drugs 0.000 description 1
- JTJMJGYZQZDUJJ-UHFFFAOYSA-N phencyclidine Chemical compound C1CCCCN1C1(C=2C=CC=CC=2)CCCCC1 JTJMJGYZQZDUJJ-UHFFFAOYSA-N 0.000 description 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
- PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 1
- 239000013600 plasmid vector Substances 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- QKTAAWLCLHMUTJ-UHFFFAOYSA-N psilocybin Chemical compound C1C=CC(OP(O)(O)=O)=C2C(CCN(C)C)=CN=C21 QKTAAWLCLHMUTJ-UHFFFAOYSA-N 0.000 description 1
- 229950005261 psilocybine Drugs 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- 230000001698 pyrogenic effect Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000003259 recombinant expression Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 229940125723 sedative agent Drugs 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical compound COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 1
- 238000011146 sterile filtration Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000008362 succinate buffer Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 229960002766 tetanus vaccines Drugs 0.000 description 1
- 238000002076 thermal analysis method Methods 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 229940044616 toll-like receptor 7 agonist Drugs 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 241000701447 unidentified baculovirus Species 0.000 description 1
- 239000013598 vector Substances 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 230000029812 viral genome replication Effects 0.000 description 1
- 239000000277 virosome Substances 0.000 description 1
- 239000011995 wilkinson's catalyst Substances 0.000 description 1
- UTODFRQBVUVYOB-UHFFFAOYSA-P wilkinson's catalyst Chemical compound [Cl-].C1=CC=CC=C1P(C=1C=CC=CC=1)(C=1C=CC=CC=1)[Rh+](P(C=1C=CC=CC=1)(C=1C=CC=CC=1)C=1C=CC=CC=1)P(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 UTODFRQBVUVYOB-UHFFFAOYSA-P 0.000 description 1
- UGOMMVLRQDMAQQ-UHFFFAOYSA-N xphos Chemical group CC(C)C1=CC(C(C)C)=CC(C(C)C)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 UGOMMVLRQDMAQQ-UHFFFAOYSA-N 0.000 description 1
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
- A61K31/66—Phosphorus compounds
- A61K31/675—Phosphorus compounds having nitrogen as a ring hetero atom, e.g. pyridoxal phosphate
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K39/00—Medicinal preparations containing antigens or antibodies
- A61K39/39—Medicinal preparations containing antigens or antibodies characterised by the immunostimulating additives, e.g. chemical adjuvants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K39/00—Medicinal preparations containing antigens or antibodies
- A61K2039/555—Medicinal preparations containing antigens or antibodies characterised by a specific combination antigen/adjuvant
- A61K2039/55511—Organic adjuvants
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Immunology (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Microbiology (AREA)
- Mycology (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261608011P | 2012-03-07 | 2012-03-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HUE030175T2 true HUE030175T2 (en) | 2017-04-28 |
Family
ID=47843276
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HUE13708142A HUE030175T2 (en) | 2012-03-07 | 2013-03-07 | Arginine salt of TLR7 agonist |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US9320748B2 (enExample) |
| EP (1) | EP2822947B1 (enExample) |
| JP (1) | JP6325986B2 (enExample) |
| CN (1) | CN104203946B (enExample) |
| AU (1) | AU2013229466A1 (enExample) |
| CA (1) | CA2865759C (enExample) |
| CY (1) | CY1118091T1 (enExample) |
| DK (1) | DK2822947T3 (enExample) |
| ES (1) | ES2597755T3 (enExample) |
| HR (1) | HRP20161354T1 (enExample) |
| HU (1) | HUE030175T2 (enExample) |
| LT (1) | LT2822947T (enExample) |
| MX (1) | MX346678B (enExample) |
| PL (1) | PL2822947T3 (enExample) |
| PT (1) | PT2822947T (enExample) |
| RU (1) | RU2014140336A (enExample) |
| SI (1) | SI2822947T1 (enExample) |
| WO (1) | WO2013131985A1 (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2443952T3 (es) | 2009-09-02 | 2014-02-21 | Novartis Ag | Composiciones inmunógenas que incluyen moduladores de la actividad de TLR |
| CN105999275A (zh) | 2010-09-01 | 2016-10-12 | 诺华有限公司 | 免疫增强剂吸附不溶性金属离子 |
| US20140112950A1 (en) | 2011-03-02 | 2014-04-24 | Manmohan Singh | Combination vaccines with lower doses of antigen and/or adjuvant |
| US9375471B2 (en) | 2012-03-08 | 2016-06-28 | Glaxosmithkline Biologicals Sa | Adjuvanted formulations of booster vaccines |
| EP3122378B1 (en) | 2014-03-26 | 2019-12-11 | GlaxoSmithKline Biologicals S.A. | Mutant staphylococcal antigens |
| EP3061826A1 (en) | 2015-02-27 | 2016-08-31 | Novartis AG | Flavivirus replicons |
| EP4114463A4 (en) * | 2020-03-01 | 2023-09-06 | Dynavax Technologies Corporation | CORONAVIRUS VACCINES INCLUDING A TLR9 AGONIST |
| WO2022192097A1 (en) * | 2021-03-06 | 2022-09-15 | Mind Medicine, Inc. | Formulations of psilocin that have enhanced stability |
| GB202215414D0 (en) | 2022-10-18 | 2022-11-30 | Glaxosmithkline Biologicals Sa | Vaccine |
Family Cites Families (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6699474B1 (en) | 1990-08-20 | 2004-03-02 | Erich Hugo Cerny | Vaccine and immunserum against drugs of abuse |
| WO1993018150A1 (en) | 1992-03-02 | 1993-09-16 | Biocine S.P.A. | Helicobacter pylori proteins useful for vaccines and diagnostics |
| FR2718452B1 (fr) | 1994-04-06 | 1996-06-28 | Pf Medicament | Elément d'immunogène, agent immunogène, composition pharmaceutique et procédé de préparation. |
| JPH10502365A (ja) | 1994-07-01 | 1998-03-03 | リカン・リミテッド | ヘリコバクタータンパク質およびワクチン |
| GB2324093A (en) | 1996-01-04 | 1998-10-14 | Rican Limited | Helicobacter pylori bacterioferritin |
| GB9828000D0 (en) | 1998-12-18 | 1999-02-10 | Chiron Spa | Antigens |
| ATE440861T1 (de) | 2000-07-03 | 2009-09-15 | Novartis Vaccines & Diagnostic | Immunisierung gegen chlamydia pneumoniae |
| FR2827605B1 (fr) | 2001-07-20 | 2004-07-16 | Pf Medicament | Nouveaux peptides derives de la proteine g du vrs et leur utilisation dans un vaccin |
| ES2312649T3 (es) | 2001-12-12 | 2009-03-01 | Novartis Vaccines And Diagnostics S.R.L. | Inmunizacion frente a chlamydia trachomatis. |
| GB0211118D0 (en) | 2002-05-15 | 2002-06-26 | Polonelli Luciano | Vaccines |
| DE60335477D1 (de) | 2002-10-11 | 2011-02-03 | Novartis Vaccines & Diagnostic | Polypeptidimpstoffe zum breiten schutz gegen hypervirulente meningokokken-linien |
| JP4896715B2 (ja) | 2003-06-26 | 2012-03-14 | ノバルティス バクシンズ アンド ダイアグノスティックス，インコーポレーテッド | Ｃｈｌａｍｙｄｉａｔｒａｃｈｏｍａｔｉｓに対する免疫原性組成物 |
| RU2006134631A (ru) | 2004-03-02 | 2008-04-10 | Чирон Корпорейшн (Us) | Иммуногенные композиции против chlamidia pneumoniae |
| ES2595363T3 (es) | 2005-02-18 | 2016-12-29 | J. Craig Venter Institute, Inc. | Sepsis asociada a las proteínas y los ácidos nucleicos de meningitis / Escherichia coli |
| US8062644B2 (en) | 2005-02-18 | 2011-11-22 | Novartis Vaccines & Diagnostics Srl. | Immunogens from uropathogenic Escherichia coli |
| EP1891096A2 (en) | 2005-05-12 | 2008-02-27 | Novartis Vaccines and Diagnostics, Inc. | Immunogenic compositions for chlamydia trachomatis |
| GB0524066D0 (en) | 2005-11-25 | 2006-01-04 | Chiron Srl | 741 ii |
| EP1976557A2 (en) | 2005-12-22 | 2008-10-08 | Novartis Vaccines and Diagnostics S.r.l. | Chlamydial antigens |
| WO2008020330A2 (en) | 2006-08-16 | 2008-02-21 | Novartis Ag | Immunogens from uropathogenic escherichia coli |
| NZ584683A (en) | 2007-10-19 | 2012-05-25 | Novartis Ag | Neisseria meningitidis serogroup B vaccine formulations |
| CA2758490C (en) | 2009-04-14 | 2023-05-02 | Novartis Ag | Compositions for immunising against staphylococcus aureus |
| ES2531115T3 (es) | 2009-06-01 | 2015-03-10 | Novartis Ag | Combinaciones de clados de RrgB neumocócicos |
| CN102762226A (zh) * | 2009-06-10 | 2012-10-31 | 诺华有限公司 | 含苯并萘啶的疫苗 |
| BR112012004275A2 (pt) | 2009-08-27 | 2016-11-16 | Novartis Ag | polipeptídios híbridos incluindo sequências meningocócicas de fhbp |
| JO3257B1 (ar) | 2009-09-02 | 2018-09-16 | Novartis Ag | مركبات وتركيبات كمعدلات لفاعلية tlr |
| ES2443952T3 (es) | 2009-09-02 | 2014-02-21 | Novartis Ag | Composiciones inmunógenas que incluyen moduladores de la actividad de TLR |
| CN105999275A (zh) | 2010-09-01 | 2016-10-12 | 诺华有限公司 | 免疫增强剂吸附不溶性金属离子 |
| EP2667852B1 (en) | 2011-01-27 | 2016-11-09 | GlaxoSmithKline Biologicals SA | Adjuvant nanoemulsions with crystallisation inhibitors |
| KR20140066212A (ko) * | 2011-09-01 | 2014-05-30 | 노파르티스 아게 | 스타필로코쿠스 아우레우스 항원의 보조제 첨가된 조제물 |
-
2013
- 2013-03-07 HR HRP20161354TT patent/HRP20161354T1/hr unknown
- 2013-03-07 PT PT137081428T patent/PT2822947T/pt unknown
- 2013-03-07 PL PL13708142T patent/PL2822947T3/pl unknown
- 2013-03-07 EP EP13708142.8A patent/EP2822947B1/en active Active
- 2013-03-07 MX MX2014010423A patent/MX346678B/es active IP Right Grant
- 2013-03-07 HU HUE13708142A patent/HUE030175T2/en unknown
- 2013-03-07 CN CN201380012851.1A patent/CN104203946B/zh active Active
- 2013-03-07 RU RU2014140336A patent/RU2014140336A/ru not_active Application Discontinuation
- 2013-03-07 DK DK13708142.8T patent/DK2822947T3/en active
- 2013-03-07 SI SI201330288A patent/SI2822947T1/sl unknown
- 2013-03-07 ES ES13708142.8T patent/ES2597755T3/es active Active
- 2013-03-07 CA CA2865759A patent/CA2865759C/en active Active
- 2013-03-07 LT LTEP13708142.8T patent/LT2822947T/lt unknown
- 2013-03-07 US US14/381,513 patent/US9320748B2/en active Active
- 2013-03-07 WO PCT/EP2013/054548 patent/WO2013131985A1/en not_active Ceased
- 2013-03-07 AU AU2013229466A patent/AU2013229466A1/en not_active Abandoned
- 2013-03-07 JP JP2014560367A patent/JP6325986B2/ja active Active
-
2016
- 2016-10-10 CY CY20161101006T patent/CY1118091T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES2597755T3 (es) | 2017-01-20 |
| EP2822947B1 (en) | 2016-08-03 |
| CN104203946A (zh) | 2014-12-10 |
| AU2013229466A1 (en) | 2014-09-04 |
| RU2014140336A (ru) | 2016-04-27 |
| PT2822947T (pt) | 2016-09-26 |
| MX346678B (es) | 2017-03-29 |
| US20150125475A1 (en) | 2015-05-07 |
| US9320748B2 (en) | 2016-04-26 |
| JP2015511957A (ja) | 2015-04-23 |
| DK2822947T3 (en) | 2016-09-19 |
| LT2822947T (lt) | 2016-10-10 |
| HRP20161354T1 (hr) | 2016-12-02 |
| EP2822947A1 (en) | 2015-01-14 |
| CN104203946B (zh) | 2017-03-22 |
| CA2865759A1 (en) | 2013-09-12 |
| PL2822947T3 (pl) | 2017-01-31 |
| JP6325986B2 (ja) | 2018-05-16 |
| CY1118091T1 (el) | 2017-06-28 |
| WO2013131985A1 (en) | 2013-09-12 |
| MX2014010423A (es) | 2014-09-22 |
| CA2865759C (en) | 2020-07-21 |
| SI2822947T1 (sl) | 2016-10-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DK2822947T3 (en) | ARGINAL SALTS OF A TLR-7 AGONIST | |
| US10098949B2 (en) | Adsorption of immunopotentiators to insoluble metal salts | |
| US20140363461A1 (en) | Adjuvanted formulations of staphylococcus aureus antigens | |
| US20230346904A1 (en) | Bacterial and viral vaccine strategy | |
| KR102077876B1 (ko) | Ｃｒｍ１９７ 담체 단백질에 커플링된 ｈｉｖ ｇｐ４１ 펩티드를 포함하는 면역원성 화합물 | |
| AU2016204453A1 (en) | Adsorption of immunopotentiators to insoluble metal salts | |
| US11793869B2 (en) | Methods for enterovirus inactivation, adjuvant adsorption and dose reduced vaccine compositions obtained thereof | |
| US20180228885A1 (en) | Bacterial and viral vaccine strategy | |
| AU2013203167A1 (en) | Adsorption of immunopotentiators to insoluble metal salts | |
| OA20569A (en) | Improved methods for enterovirus inactivation, adjuvant adsorption and dose reduced vaccine compositions obtained thereof. | |
| HK1259511A1 (en) | Bacterial and viral vaccine strategy |