JP2016540050A5 - - Google Patents
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- JP2016540050A5 JP2016540050A5 JP2016555933A JP2016555933A JP2016540050A5 JP 2016540050 A5 JP2016540050 A5 JP 2016540050A5 JP 2016555933 A JP2016555933 A JP 2016555933A JP 2016555933 A JP2016555933 A JP 2016555933A JP 2016540050 A5 JP2016540050 A5 JP 2016540050A5
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- Prior art keywords
- amino acid
- moiety
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- acid residues
- compound
- Prior art date
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- 125000000539 amino acid group Chemical group 0.000 claims description 76
- 150000001875 compounds Chemical class 0.000 claims description 54
- 230000003308 immunostimulating effect Effects 0.000 claims description 32
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 31
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 150000001413 amino acids Chemical class 0.000 claims description 15
- 239000008194 pharmaceutical composition Substances 0.000 claims description 15
- 230000002163 immunogen Effects 0.000 claims description 9
- 230000028993 immune response Effects 0.000 claims description 8
- 102000012064 NLR Proteins Human genes 0.000 claims description 6
- 108091005686 NOD-like receptors Proteins 0.000 claims description 6
- 239000000556 agonist Substances 0.000 claims description 6
- 229940024606 amino acid Drugs 0.000 claims description 6
- 235000001014 amino acid Nutrition 0.000 claims description 6
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 claims description 6
- 230000004936 stimulating effect Effects 0.000 claims description 6
- BSOQXXWZTUDTEL-ZUYCGGNHSA-N muramyl dipeptide Chemical group OC(=O)CC[C@H](C(N)=O)NC(=O)[C@H](C)NC(=O)[C@@H](C)O[C@H]1[C@H](O)[C@@H](CO)O[C@@H](O)[C@@H]1NC(C)=O BSOQXXWZTUDTEL-ZUYCGGNHSA-N 0.000 claims description 5
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 4
- 206010028980 Neoplasm Diseases 0.000 claims description 4
- 102100039390 Toll-like receptor 7 Human genes 0.000 claims description 4
- 239000000427 antigen Substances 0.000 claims description 4
- 102000036639 antigens Human genes 0.000 claims description 4
- 108091007433 antigens Proteins 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000006850 spacer group Chemical group 0.000 claims description 4
- RHKWIGHJGOEUSM-UHFFFAOYSA-N 3h-imidazo[4,5-h]quinoline Chemical group C1=CN=C2C(N=CN3)=C3C=CC2=C1 RHKWIGHJGOEUSM-UHFFFAOYSA-N 0.000 claims description 3
- 201000010099 disease Diseases 0.000 claims description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 3
- 230000002209 hydrophobic effect Effects 0.000 claims description 3
- AMJRPMCWKISZBC-IDWMTUBTSA-N (2S,6R)-2,6-diamino-4-[(2R)-2-amino-2-carboxyethyl]-5-oxononanedioic acid Chemical group N[C@H](CCC(=O)O)C(=O)C(C[C@H](N)C(=O)O)C[C@@H](N)C(=O)O AMJRPMCWKISZBC-IDWMTUBTSA-N 0.000 claims description 2
- 101710183446 C-type lectin domain family 4 member E Proteins 0.000 claims description 2
- 102100040839 C-type lectin domain family 6 member A Human genes 0.000 claims description 2
- 101710125370 C-type lectin domain family 6 member A Proteins 0.000 claims description 2
- 102100040840 C-type lectin domain family 7 member A Human genes 0.000 claims description 2
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- 239000004471 Glycine Substances 0.000 claims description 2
- 101000874165 Homo sapiens Probable ATP-dependent RNA helicase DDX41 Proteins 0.000 claims description 2
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 claims description 2
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims description 2
- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 claims description 2
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 claims description 2
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 claims description 2
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims description 2
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 claims description 2
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 claims description 2
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 claims description 2
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 claims description 2
- 102100035727 Probable ATP-dependent RNA helicase DDX41 Human genes 0.000 claims description 2
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 claims description 2
- 229940123384 Toll-like receptor (TLR) agonist Drugs 0.000 claims description 2
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 claims description 2
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 claims description 2
- 239000002671 adjuvant Substances 0.000 claims description 2
- 235000004279 alanine Nutrition 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 230000000890 antigenic effect Effects 0.000 claims description 2
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 108010025838 dectin 1 Proteins 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 230000000694 effects Effects 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 150000002430 hydrocarbons Chemical class 0.000 claims description 2
- 229960000310 isoleucine Drugs 0.000 claims description 2
- AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 claims description 2
- 150000002632 lipids Chemical class 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 229930182817 methionine Natural products 0.000 claims description 2
- 125000001446 muramyl group Chemical group N[C@@H](C=O)[C@@H](O[C@@H](C(=O)*)C)[C@H](O)[C@H](O)CO 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 244000052769 pathogen Species 0.000 claims description 2
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 claims description 2
- 239000004474 valine Substances 0.000 claims description 2
- 108010060825 Toll-Like Receptor 7 Proteins 0.000 claims 3
- 229960003767 alanine Drugs 0.000 claims 3
- 108010042708 Acetylmuramyl-Alanyl-Isoglutamine Proteins 0.000 claims 2
- 229940124614 TLR 8 agonist Drugs 0.000 claims 2
- 125000004857 imidazopyridinyl group Chemical group N1C(=NC2=C1C=CC=N2)* 0.000 claims 2
- 108700017543 murabutide Proteins 0.000 claims 2
- KEOKIKNGKDOHGH-CEXWTWQISA-N (2r,6s)-2-amino-6-[[(4r)-4-carboxy-4-(dodecanoylamino)butanoyl]amino]heptanedioic acid Chemical compound CCCCCCCCCCCC(=O)N[C@@H](C(O)=O)CCC(=O)N[C@H](C(O)=O)CCC[C@@H](N)C(O)=O KEOKIKNGKDOHGH-CEXWTWQISA-N 0.000 claims 1
- NMAKGCMEDYICRN-UHFFFAOYSA-N 2-[[4-[2-[2-(2-acetamido-4,5,6-trihydroxy-1-oxohexan-3-yl)oxypropanoylamino]propanoylamino]-5-amino-5-oxopentanoyl]amino]-6-aminoheptanedioic acid Chemical compound OCC(O)C(O)C(C(NC(C)=O)C=O)OC(C)C(=O)NC(C)C(=O)NC(C(N)=O)CCC(=O)NC(CCCC(N)C(O)=O)C(O)=O NMAKGCMEDYICRN-UHFFFAOYSA-N 0.000 claims 1
- 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 claims 1
- 101001125032 Homo sapiens Nucleotide-binding oligomerization domain-containing protein 1 Proteins 0.000 claims 1
- 101001125026 Homo sapiens Nucleotide-binding oligomerization domain-containing protein 2 Proteins 0.000 claims 1
- FMNCPUGORYYCEM-AXTSPUMRSA-N L-alanyl-gamma-D-glutamyl-meso-diaminopimelic acid Chemical compound C[C@H](N)C(=O)N[C@@H](C(O)=O)CCC(=O)N[C@@H](C(O)=O)CCC[C@H](N)C(O)=O FMNCPUGORYYCEM-AXTSPUMRSA-N 0.000 claims 1
- 239000004472 Lysine Substances 0.000 claims 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims 1
- 102100029424 Nucleotide-binding oligomerization domain-containing protein 1 Human genes 0.000 claims 1
- 102100029441 Nucleotide-binding oligomerization domain-containing protein 2 Human genes 0.000 claims 1
- 239000013566 allergen Substances 0.000 claims 1
- ISYJGPYKJNWIQE-BNOMVYTKSA-N butyl (2r)-2-[[(2s)-2-[[(2r)-2-[(2r,3r,4r,5r)-2-acetamido-4,5,6-trihydroxy-1-oxohexan-3-yl]oxypropanoyl]amino]propanoyl]amino]-5-amino-5-oxopentanoate Chemical compound CCCCOC(=O)[C@@H](CCC(N)=O)NC(=O)[C@H](C)NC(=O)[C@@H](C)O[C@@H]([C@H](O)[C@H](O)CO)[C@@H](NC(C)=O)C=O ISYJGPYKJNWIQE-BNOMVYTKSA-N 0.000 claims 1
- 230000007423 decrease Effects 0.000 claims 1
- QIFGMZZTJRULMA-XLPZGREQSA-N gamma-D-glutamyl-meso-diaminopimelic acid Chemical compound OC(=O)[C@@H](N)CCC[C@H](C(O)=O)NC(=O)CC[C@@H](N)C(O)=O QIFGMZZTJRULMA-XLPZGREQSA-N 0.000 claims 1
- 125000003588 lysine group Chemical group [H]N([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 claims 1
- 229950009571 murabutide Drugs 0.000 claims 1
- 108700030295 muramylNAc-Ala-isoGln-Lys-tripeptide Proteins 0.000 claims 1
- 238000000034 method Methods 0.000 description 6
- 229960001438 immunostimulant agent Drugs 0.000 description 3
- 239000003022 immunostimulating agent Substances 0.000 description 3
- 230000001717 pathogenic effect Effects 0.000 description 3
- 208000023275 Autoimmune disease Diseases 0.000 description 2
- BBTRBXPZJTVATE-UHFFFAOYSA-N CCOCc1nc(c(N)nc2c3cccc2)c3[n]1C Chemical compound CCOCc1nc(c(N)nc2c3cccc2)c3[n]1C BBTRBXPZJTVATE-UHFFFAOYSA-N 0.000 description 2
- 201000011510 cancer Diseases 0.000 description 2
- 210000003722 extracellular fluid Anatomy 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 101000669402 Homo sapiens Toll-like receptor 7 Proteins 0.000 description 1
- 101000800483 Homo sapiens Toll-like receptor 8 Proteins 0.000 description 1
- 102100033110 Toll-like receptor 8 Human genes 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1321242.8 | 2013-12-02 | ||
| GBGB1321242.8A GB201321242D0 (en) | 2013-12-02 | 2013-12-02 | Immunogenic compound |
| PCT/GB2014/053577 WO2015082905A1 (en) | 2013-12-02 | 2014-12-02 | Immunogenic compound |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020185572A Division JP7095053B2 (ja) | 2013-12-02 | 2020-11-06 | 免疫原性化合物 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016540050A JP2016540050A (ja) | 2016-12-22 |
| JP2016540050A5 true JP2016540050A5 (cg-RX-API-DMAC7.html) | 2018-01-25 |
| JP6792452B2 JP6792452B2 (ja) | 2020-11-25 |
Family
ID=49979653
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016555933A Expired - Fee Related JP6792452B2 (ja) | 2013-12-02 | 2014-12-02 | 免疫原性化合物 |
| JP2020185572A Active JP7095053B2 (ja) | 2013-12-02 | 2020-11-06 | 免疫原性化合物 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020185572A Active JP7095053B2 (ja) | 2013-12-02 | 2020-11-06 | 免疫原性化合物 |
Country Status (10)
| Country | Link |
|---|---|
| US (4) | US9962453B2 (cg-RX-API-DMAC7.html) |
| EP (1) | EP3077052A1 (cg-RX-API-DMAC7.html) |
| JP (2) | JP6792452B2 (cg-RX-API-DMAC7.html) |
| KR (1) | KR102356869B1 (cg-RX-API-DMAC7.html) |
| CN (1) | CN105873638A (cg-RX-API-DMAC7.html) |
| BR (1) | BR112016012528A2 (cg-RX-API-DMAC7.html) |
| CA (1) | CA2931933A1 (cg-RX-API-DMAC7.html) |
| EA (1) | EA201691146A1 (cg-RX-API-DMAC7.html) |
| GB (1) | GB201321242D0 (cg-RX-API-DMAC7.html) |
| WO (1) | WO2015082905A1 (cg-RX-API-DMAC7.html) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015077717A1 (en) | 2013-11-25 | 2015-05-28 | The Broad Institute Inc. | Compositions and methods for diagnosing, evaluating and treating cancer by means of the dna methylation status |
| GB201321242D0 (en) * | 2013-12-02 | 2014-01-15 | Immune Targeting Systems Its Ltd | Immunogenic compound |
| US11725237B2 (en) | 2013-12-05 | 2023-08-15 | The Broad Institute Inc. | Polymorphic gene typing and somatic change detection using sequencing data |
| NZ721908A (en) | 2013-12-20 | 2022-12-23 | Massachusetts Gen Hospital | Combination therapy with neoantigen vaccine |
| US10975442B2 (en) | 2014-12-19 | 2021-04-13 | Massachusetts Institute Of Technology | Molecular biomarkers for cancer immunotherapy |
| US10993997B2 (en) | 2014-12-19 | 2021-05-04 | The Broad Institute, Inc. | Methods for profiling the t cell repertoire |
| CA3029902A1 (en) | 2016-07-07 | 2018-01-11 | The Board Of Trustees Of The Leland Stanford Junior University | Antibody adjuvant conjugates |
| WO2018175854A1 (en) * | 2017-03-23 | 2018-09-27 | The Children's Medical Center Corporation | Methods and compositions relating to adjuvants |
| IL302880A (en) | 2017-04-04 | 2023-07-01 | Avidea Tech Inc | Peptide-based ingredients, production methods, and their uses for inducing an immune response |
| US10618896B2 (en) | 2017-08-22 | 2020-04-14 | Dynavax Technologies Corporation | Alkyl chain modified imidazoquinoline TLR7/8 agonist compounds and uses thereof |
| EP3710059A1 (en) | 2017-11-14 | 2020-09-23 | Dynavax Technologies Corporation | Cleavable conjugates of tlr7/8 agonist compounds, methods for preparation, and uses thereof |
| WO2020010394A1 (en) * | 2018-07-10 | 2020-01-16 | Seqirus Pty Ltd | Removal of agglomerates |
| EP3937984A1 (en) | 2019-03-15 | 2022-01-19 | Bolt Biotherapeutics, Inc. | Immunoconjugates targeting her2 |
| WO2020205996A2 (en) * | 2019-04-01 | 2020-10-08 | Altimmune Uk Ltd | Locally acting toll-like receptor 7 (tlr7) and/or tlr8 agonist immunotherapy compounds and their uses |
| WO2023085956A1 (en) * | 2021-11-09 | 2023-05-19 | Avalia Immunotherapies Limited | Novel therapeutic vaccines |
| TWI894573B (zh) * | 2022-06-09 | 2025-08-21 | 中央研究院 | Nod1調節劑及其用途 |
| KR102784104B1 (ko) * | 2024-04-04 | 2025-03-24 | 대한민국(방위사업청장) | 이미퀴모드 및 Nod2 수용체 자극 성분 또는 박테리아를 포함하는 면역 어쥬번트 |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4801575A (en) | 1986-07-30 | 1989-01-31 | The Regents Of The University Of California | Chimeric peptides for neuropeptide delivery through the blood-brain barrier |
| US5294605A (en) | 1990-07-19 | 1994-03-15 | The Scripps Research Institute | Amphiphilic peptide compositions and analogues thereof |
| FR2744123B1 (fr) * | 1996-01-26 | 1998-04-17 | Carelli Claude Marcel Henri | Molecules biologiquement actives plus particulierement peptidiques ayant un effet potentialisateur de l'activite biologique de l'hormone de croissance |
| EP1450804B9 (en) | 2001-11-29 | 2009-04-01 | 3M Innovative Properties Company | Pharmaceutical formulations comprising an immune response modifier |
| CA2495570C (en) | 2002-08-15 | 2012-12-04 | 3M Innovative Properties Company | Immunostimulatory compositions and methods of stimulating an immune response |
| AU2004291122A1 (en) | 2003-11-14 | 2005-06-02 | 3M Innovative Properties Company | Hydroxylamine substituted imidazo ring compounds |
| GB0408164D0 (en) | 2004-04-13 | 2004-05-19 | Immune Targeting Systems Ltd | Antigen delivery vectors and constructs |
| GB0716992D0 (en) | 2007-08-31 | 2007-10-10 | Immune Targeting Systems Its L | Influenza antigen delivery vectors and constructs |
| WO2006116475A2 (en) | 2005-04-25 | 2006-11-02 | 3M Innovative Properties Company | Immunostimulatory compositions |
| SI2510946T1 (sl) | 2007-02-07 | 2015-12-31 | The Regents Of The University Of California | Konjugati sintetičnih agonistov TLR in njihove uporabe |
| ES2532896T5 (es) * | 2008-05-14 | 2018-03-20 | Immatics Biotechnologies Gmbh | Péptidos del MHC de clase II novedosos y potentes derivados de survivina y neurocan |
| HRP20180063T1 (hr) | 2008-10-24 | 2018-02-23 | Glaxosmithkline Biologicals Sa | Lipidirani derivati imidazokinolina |
| EP2387421A1 (en) * | 2009-01-14 | 2011-11-23 | SKU Asset Management GmbH | Compounds comprising n-formyl-methionine residues and tumor-targeting peptides |
| WO2011068233A1 (en) | 2009-12-03 | 2011-06-09 | Dainippon Sumitomo Pharma Co., Ltd. | Imidazoquinolines which act via toll - like receptors (tlr) |
| US8916162B2 (en) | 2010-02-20 | 2014-12-23 | Alexey Gennadievich Zdanovsky | Botulinum neurotoxin antigenic compositions and methods |
| CN105294684B (zh) | 2010-08-17 | 2018-04-06 | 3M创新有限公司 | 脂质化免疫反应调节剂化合物的组合物、制剂及方法 |
| GB201022147D0 (en) * | 2010-12-31 | 2011-02-16 | Immune Targeting Systems Its Ltd | Formulation |
| WO2012113413A1 (en) * | 2011-02-21 | 2012-08-30 | Curevac Gmbh | Vaccine composition comprising complexed immunostimulatory nucleic acids and antigens packaged with disulfide-linked polyethyleneglycol/peptide conjugates |
| US8728486B2 (en) | 2011-05-18 | 2014-05-20 | University Of Kansas | Toll-like receptor-7 and -8 modulatory 1H imidazoquinoline derived compounds |
| WO2012167088A1 (en) | 2011-06-03 | 2012-12-06 | 3M Innovative Properties Company | Heterobifunctional linkers with polyethylene glycol segments and immune response modifier conjugates made therefrom |
| GB201321242D0 (en) * | 2013-12-02 | 2014-01-15 | Immune Targeting Systems Its Ltd | Immunogenic compound |
-
2013
- 2013-12-02 GB GBGB1321242.8A patent/GB201321242D0/en not_active Ceased
-
2014
- 2014-12-02 WO PCT/GB2014/053577 patent/WO2015082905A1/en not_active Ceased
- 2014-12-02 JP JP2016555933A patent/JP6792452B2/ja not_active Expired - Fee Related
- 2014-12-02 EA EA201691146A patent/EA201691146A1/ru unknown
- 2014-12-02 US US15/100,800 patent/US9962453B2/en active Active
- 2014-12-02 KR KR1020167017734A patent/KR102356869B1/ko not_active Expired - Fee Related
- 2014-12-02 CN CN201480071742.1A patent/CN105873638A/zh active Pending
- 2014-12-02 CA CA2931933A patent/CA2931933A1/en active Pending
- 2014-12-02 EP EP14809960.9A patent/EP3077052A1/en not_active Withdrawn
- 2014-12-02 BR BR112016012528A patent/BR112016012528A2/pt not_active IP Right Cessation
-
2018
- 2018-05-02 US US15/968,839 patent/US10434183B2/en not_active Expired - Fee Related
-
2019
- 2019-10-07 US US16/595,311 patent/US10849984B2/en not_active Expired - Fee Related
-
2020
- 2020-11-06 US US17/091,106 patent/US20210145975A1/en not_active Abandoned
- 2020-11-06 JP JP2020185572A patent/JP7095053B2/ja active Active
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