JP2016509081A5 - - Google Patents
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- Publication number
- JP2016509081A5 JP2016509081A5 JP2015548822A JP2015548822A JP2016509081A5 JP 2016509081 A5 JP2016509081 A5 JP 2016509081A5 JP 2015548822 A JP2015548822 A JP 2015548822A JP 2015548822 A JP2015548822 A JP 2015548822A JP 2016509081 A5 JP2016509081 A5 JP 2016509081A5
- Authority
- JP
- Japan
- Prior art keywords
- sugar
- tempo
- carrier protein
- nitroxyl radical
- oxidant
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 238000000034 method Methods 0.000 claims 19
- -1 nitroxyl radical compound Chemical class 0.000 claims 15
- 102000014914 Carrier Proteins Human genes 0.000 claims 12
- 108010078791 Carrier Proteins Proteins 0.000 claims 12
- 150000004676 glycans Chemical class 0.000 claims 9
- 230000001590 oxidative effect Effects 0.000 claims 9
- 229920001282 polysaccharide Polymers 0.000 claims 9
- 239000005017 polysaccharide Substances 0.000 claims 9
- 239000000203 mixture Substances 0.000 claims 8
- 239000007800 oxidant agent Substances 0.000 claims 8
- 230000002163 immunogen Effects 0.000 claims 7
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-Chlorosuccinimide Substances ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 claims 6
- 125000003172 aldehyde group Chemical group 0.000 claims 6
- 150000003138 primary alcohols Chemical class 0.000 claims 5
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methyl-cyclopentane Natural products CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 claims 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 3
- 150000001720 carbohydrates Chemical class 0.000 claims 3
- 235000014633 carbohydrates Nutrition 0.000 claims 3
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 claims 2
- LQZMLBORDGWNPD-UHFFFAOYSA-N N-iodosuccinimide Chemical compound IN1C(=O)CCC1=O LQZMLBORDGWNPD-UHFFFAOYSA-N 0.000 claims 2
- 241000588650 Neisseria meningitidis Species 0.000 claims 2
- RPDUDBYMNGAHEM-UHFFFAOYSA-N PROXYL Chemical compound CC1(C)CCC(C)(C)N1[O] RPDUDBYMNGAHEM-UHFFFAOYSA-N 0.000 claims 2
- 125000003277 amino group Chemical group 0.000 claims 2
- 239000003125 aqueous solvent Substances 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 238000005502 peroxidation Methods 0.000 claims 2
- GPECWDAWQNNPNX-UHFFFAOYSA-N (1-$l^{1}-oxidanyl-2,2,6,6-tetramethylpiperidin-4-yl) dihydrogen phosphate Chemical compound CC1(C)CC(OP(O)(O)=O)CC(C)(C)N1[O] GPECWDAWQNNPNX-UHFFFAOYSA-N 0.000 claims 1
- FWQKPTXRJZOQGN-UHFFFAOYSA-N (2,2,6,6-tetramethyl-1-oxidopiperidin-1-ium-4-yl) methanesulfonate Chemical group CC1(C)CC(OS(C)(=O)=O)CC(C)(C)[NH+]1[O-] FWQKPTXRJZOQGN-UHFFFAOYSA-N 0.000 claims 1
- YRIZYWQGELRKNT-UHFFFAOYSA-N 1,3,5-trichloro-1,3,5-triazinane-2,4,6-trione Chemical compound ClN1C(=O)N(Cl)C(=O)N(Cl)C1=O YRIZYWQGELRKNT-UHFFFAOYSA-N 0.000 claims 1
- HHBCEKAWSILOOP-UHFFFAOYSA-N 1,3-dibromo-1,3,5-triazinane-2,4,6-trione Chemical compound BrN1C(=O)NC(=O)N(Br)C1=O HHBCEKAWSILOOP-UHFFFAOYSA-N 0.000 claims 1
- FGWPUTALVVHOGA-UHFFFAOYSA-N 1,3-diiodo-1,3,5-triazinane-2,4,6-trione Chemical compound IN1C(=O)NC(=O)N(I)C1=O FGWPUTALVVHOGA-UHFFFAOYSA-N 0.000 claims 1
- OCIQOBBYJWEKSA-UHFFFAOYSA-N 1-$l^{1}-oxidanyl-2,2,6,6-tetramethylpiperidine-4-carbonitrile Chemical compound CC1(C)CC(C#N)CC(C)(C)N1[O] OCIQOBBYJWEKSA-UHFFFAOYSA-N 0.000 claims 1
- RPAZYIOIDZRJOO-UHFFFAOYSA-N 16-DOXYL-stearic acid Chemical compound OC(=O)CCCCCCCCCCCCCCC1(CC)OCC(C)(C)N1[O] RPAZYIOIDZRJOO-UHFFFAOYSA-N 0.000 claims 1
- RAOLMQDPNYDCEF-UHFFFAOYSA-N 2-bromo-n-(1-$l^{1}-oxidanyl-2,2,6,6-tetramethylpiperidin-4-yl)acetamide Chemical compound CC1(C)CC(NC(=O)CBr)CC(C)(C)N1[O] RAOLMQDPNYDCEF-UHFFFAOYSA-N 0.000 claims 1
- MMNYKXJVNIIIEG-UHFFFAOYSA-N 3-(aminomethyl)-PROXYL Chemical compound CC1(C)CC(CN)C(C)(C)N1[O] MMNYKXJVNIIIEG-UHFFFAOYSA-N 0.000 claims 1
- GEPIUTWNBHBHIO-UHFFFAOYSA-N 3-carboxy-PROXYL Chemical compound CC1(C)CC(C(O)=O)C(C)(C)N1[O] GEPIUTWNBHBHIO-UHFFFAOYSA-N 0.000 claims 1
- RQRRZZIMMXPAGX-UHFFFAOYSA-N 3-cyano-PROXYL Chemical compound CC1(C)CC(C#N)C(C)(C)N1[O] RQRRZZIMMXPAGX-UHFFFAOYSA-N 0.000 claims 1
- UCTVRHAKQRFPEZ-UHFFFAOYSA-N 4-(2-iodacetamido)-TEMPO Chemical compound CC1(C)CC(NC(=O)CI)CC(C)(C)N1[O] UCTVRHAKQRFPEZ-UHFFFAOYSA-N 0.000 claims 1
- UXBLSWOMIHTQPH-UHFFFAOYSA-N 4-acetamido-TEMPO Chemical group CC(=O)NC1CC(C)(C)N([O])C(C)(C)C1 UXBLSWOMIHTQPH-UHFFFAOYSA-N 0.000 claims 1
- CYQGCJQJIOARKD-UHFFFAOYSA-N 4-carboxy-TEMPO Chemical compound CC1(C)CC(C(O)=O)CC(C)(C)N1[O] CYQGCJQJIOARKD-UHFFFAOYSA-N 0.000 claims 1
- UZFMOKQJFYMBGY-UHFFFAOYSA-N 4-hydroxy-TEMPO Chemical compound CC1(C)CC(O)CC(C)(C)N1[O] UZFMOKQJFYMBGY-UHFFFAOYSA-N 0.000 claims 1
- BKENZAFIBRCMKD-UHFFFAOYSA-N 4-isothiocyanato-1-$l^{1}-oxidanyl-2,2,6,6-tetramethylpiperidine Chemical compound CC1(C)CC(N=C=S)CC(C)(C)N1[O] BKENZAFIBRCMKD-UHFFFAOYSA-N 0.000 claims 1
- SFXHWRCRQNGVLJ-UHFFFAOYSA-N 4-methoxy-TEMPO Chemical compound COC1CC(C)(C)N([O])C(C)(C)C1 SFXHWRCRQNGVLJ-UHFFFAOYSA-N 0.000 claims 1
- WSGDRFHJFJRSFY-UHFFFAOYSA-N 4-oxo-TEMPO Chemical compound CC1(C)CC(=O)CC(C)(C)N1[O] WSGDRFHJFJRSFY-UHFFFAOYSA-N 0.000 claims 1
- PYDZKXQLRMNQFK-UHFFFAOYSA-N 5-DOXYL-stearic acid Chemical compound CCCCCCCCCCCCCC1(CCCC(O)=O)OCC(C)(C)N1[O] PYDZKXQLRMNQFK-UHFFFAOYSA-N 0.000 claims 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 1
- 241000588724 Escherichia coli Species 0.000 claims 1
- 201000005702 Pertussis Diseases 0.000 claims 1
- 241000589516 Pseudomonas Species 0.000 claims 1
- 241000191940 Staphylococcus Species 0.000 claims 1
- 241000194017 Streptococcus Species 0.000 claims 1
- QYTDEUPAUMOIOP-UHFFFAOYSA-N TEMPO Chemical group CC1(C)CCCC(C)(C)N1[O] QYTDEUPAUMOIOP-UHFFFAOYSA-N 0.000 claims 1
- 206010043376 Tetanus Diseases 0.000 claims 1
- 239000000010 aprotic solvent Substances 0.000 claims 1
- 230000001580 bacterial effect Effects 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- CEJLBZWIKQJOAT-UHFFFAOYSA-N dichloroisocyanuric acid Chemical compound ClN1C(=O)NC(=O)N(Cl)C1=O CEJLBZWIKQJOAT-UHFFFAOYSA-N 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 206010013023 diphtheria Diseases 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 238000000265 homogenisation Methods 0.000 claims 1
- 230000003647 oxidation Effects 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 239000003053 toxin Substances 0.000 claims 1
- 231100000765 toxin Toxicity 0.000 claims 1
- ZKWDCFPLNQTHSH-UHFFFAOYSA-N tribromoisocyanuric acid Chemical compound BrN1C(=O)N(Br)C(=O)N(Br)C1=O ZKWDCFPLNQTHSH-UHFFFAOYSA-N 0.000 claims 1
- 229960005486 vaccine Drugs 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261740311P | 2012-12-20 | 2012-12-20 | |
| US61/740,311 | 2012-12-20 | ||
| PCT/IB2013/060933 WO2014097099A2 (en) | 2012-12-20 | 2013-12-13 | Glycoconjugation process |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018044572A Division JP6686057B2 (ja) | 2012-12-20 | 2018-03-12 | 糖複合化方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016509081A JP2016509081A (ja) | 2016-03-24 |
| JP2016509081A5 true JP2016509081A5 (https=) | 2016-09-01 |
| JP6502262B2 JP6502262B2 (ja) | 2019-04-17 |
Family
ID=50070610
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015548822A Active JP6502262B2 (ja) | 2012-12-20 | 2013-12-13 | 糖複合化方法 |
| JP2018044572A Active JP6686057B2 (ja) | 2012-12-20 | 2018-03-12 | 糖複合化方法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018044572A Active JP6686057B2 (ja) | 2012-12-20 | 2018-03-12 | 糖複合化方法 |
Country Status (21)
| Country | Link |
|---|---|
| US (5) | US10392420B2 (https=) |
| EP (3) | EP2935299B1 (https=) |
| JP (2) | JP6502262B2 (https=) |
| KR (2) | KR101787217B1 (https=) |
| CN (3) | CN108524931B (https=) |
| AU (2) | AU2013365873B2 (https=) |
| BR (2) | BR122020000550B1 (https=) |
| CA (2) | CA2943263C (https=) |
| DK (2) | DK3363806T3 (https=) |
| ES (2) | ES2933127T3 (https=) |
| FI (1) | FI3363806T3 (https=) |
| FR (2) | FR22C1038I2 (https=) |
| HR (1) | HRP20221438T1 (https=) |
| HU (2) | HUE047120T2 (https=) |
| IL (2) | IL274500B2 (https=) |
| MX (2) | MX379386B (https=) |
| PL (2) | PL2935299T3 (https=) |
| PT (2) | PT2935299T (https=) |
| RU (1) | RU2672053C2 (https=) |
| SI (2) | SI3363806T1 (https=) |
| WO (1) | WO2014097099A2 (https=) |
Families Citing this family (58)
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| BR112016015835B1 (pt) * | 2014-01-21 | 2023-12-26 | Pfizer Inc | Processo de preparação de conjugados compreendendo polissacarídeos capsulares de streptococcus pneumoniae |
| US11160855B2 (en) | 2014-01-21 | 2021-11-02 | Pfizer Inc. | Immunogenic compositions comprising conjugated capsular saccharide antigens and uses thereof |
| CN110859957B (zh) | 2014-01-21 | 2024-04-12 | 辉瑞公司 | 包含缀合荚膜糖抗原的免疫原性组合物及其用途 |
| PL3096786T3 (pl) * | 2014-01-21 | 2021-11-08 | Pfizer Inc. | Polisacharydy otoczkowe streptococcus pneumoniae i ich koniugaty |
| WO2015181834A2 (en) | 2014-05-24 | 2015-12-03 | Biological E Limited | Novel semi-synthetic meningococcal conjugate vaccine |
| HUE062499T2 (hu) | 2015-01-15 | 2023-11-28 | Pfizer | Pneumococcus-vakcinákban történõ alkalmazásra szolgáló immunogén készítmények |
| MY182282A (en) * | 2015-05-04 | 2021-01-18 | Pfizer | Group b streptococcus polysaccharide-protein conjugates, methods for producing conjugates, immunogenic compositions comprising conjugates, and uses thereof |
| KR102225282B1 (ko) * | 2015-07-21 | 2021-03-10 | 화이자 인코포레이티드 | 접합된 캡슐형 사카라이드 항원을 포함하는 면역원성 조성물, 그를 포함하는 키트 및 그의 용도 |
| KR20200038339A (ko) * | 2015-09-10 | 2020-04-10 | 인벤트프라이즈 엘엘씨 | 다가 vlp 접합체 |
| JP6884145B2 (ja) | 2015-11-20 | 2021-06-09 | ファイザー・インク | 肺炎連鎖球菌ワクチンにおいて用いるための免疫原性組成物 |
| JP6630440B2 (ja) | 2015-12-17 | 2020-01-15 | マックス プランク ゲゼルシャフト ツゥアー フェデルゥン デル ヴィッセンシャフテン エー フォー | ストレプトコッカス ニューモニアエ（Ｓｔｒｅｐｔｏｃｏｃｃｕｓ ｐｎｅｕｍｏｎｉａｅ）血清型２に対する合成ワクチン |
| EP3181148A1 (en) * | 2015-12-17 | 2017-06-21 | Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V. | Synthetic vaccines against streptococcus pneumoniae serotype 2 |
| BR112019003992A2 (pt) | 2016-09-02 | 2019-05-28 | Sanofi Pasteur Inc | vacina contra neisseria meningitidis |
| US11027005B2 (en) * | 2016-10-20 | 2021-06-08 | Km Biologics Co., Ltd. | Method for producing Hib conjugate vaccine using PRP with lowered molecular weight |
| US10751402B2 (en) | 2016-11-09 | 2020-08-25 | Pfizer Inc. | Immunogenic compositions and uses thereof |
| WO2018119142A1 (en) | 2016-12-21 | 2018-06-28 | Amgen Inc. | Anti-tnf alpha antibody formulations |
| BR112019014833A2 (pt) | 2017-01-20 | 2020-04-14 | Pfizer | composições imunogênicas para uso em vacinas pneumococais |
| CN110225757A (zh) * | 2017-01-31 | 2019-09-10 | 默沙东公司 | 由肺炎链球菌血清型19f生产荚膜多糖蛋白缀合物的方法 |
| EP4656208A3 (en) | 2017-01-31 | 2026-03-04 | Merck Sharp & Dohme LLC | Methods for making polysaccharide-protein conjugates |
| JP7680185B2 (ja) | 2017-02-24 | 2025-05-20 | メルク・シャープ・アンド・ドーム・エルエルシー | 肺炎連鎖球菌多糖－タンパク質コンジュゲートの免疫原性の増強 |
| US10729763B2 (en) | 2017-06-10 | 2020-08-04 | Inventprise, Llc | Mixtures of polysaccharide-protein pegylated compounds |
| WO2018227177A1 (en) | 2017-06-10 | 2018-12-13 | Inventprise, Llc | Multivalent conjugate vaccines with bivalent or multivalent conjugate polysaccharides that provide improved immunogenicity and avidity |
| MX394767B (es) | 2017-09-07 | 2025-03-24 | Merck Sharp & Dohme Llc | Polisacaridos neumococicos y su uso en conjugados de polisacarido inmunogenico con proteina transportadora. |
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| CN111093650B (zh) | 2017-09-07 | 2024-03-01 | 默沙东有限责任公司 | 肺炎球菌多糖及其在免疫原性多糖-载体蛋白缀合物中的用途 |
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| CN109879967A (zh) * | 2017-12-15 | 2019-06-14 | 苏州和锐生物科技有限公司 | 一种乙酰氨基葡萄糖偶联物的制备方法及应用 |
| WO2019178699A1 (en) * | 2018-03-23 | 2019-09-26 | Koranex Capital | Precision glycoconjugates as therapeutic tools |
| EP3788143B1 (en) | 2018-04-30 | 2023-06-28 | Merck Sharp & Dohme LLC | Methods for providing a homogenous solution of lyophilized mutant diptheria toxin in dimethylsulfoxide |
| EP3787673A4 (en) | 2018-04-30 | 2022-04-27 | Merck Sharp & Dohme Corp. | Methods for producing streptococcus pneumoniae capsular polysaccharide carrier protein conjugates |
| US12144855B2 (en) | 2018-04-30 | 2024-11-19 | Merck Sharp & Dohme Llc | Methods for producing streptococcus pneumoniae capsular polysaccharide carrier protein conjugates from lyospheres |
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| MX2021003358A (es) * | 2018-09-23 | 2021-05-27 | Biological E Ltd | Polisacaridos capsulares purificados de streptococcus pneumoniae. |
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| WO2022035816A1 (en) | 2020-08-10 | 2022-02-17 | Inventprise, Llc | Multivalent pneumococcal glycoconjugate vaccines containing emerging serotype 24f |
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| AU2021342797B2 (en) | 2020-09-17 | 2024-02-08 | Janssen Pharmaceuticals, Inc. | Multivalent vaccine compositions and uses thereof |
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| CA3200602A1 (en) | 2020-11-04 | 2022-05-12 | Pfizer Inc. | Immunogenic compositions for use in pneumococcal vaccines |
| JP7804673B2 (ja) * | 2020-11-10 | 2026-01-22 | ファイザー・インク | コンジュゲートさせた莢膜糖抗原を含む免疫原性組成物およびその使用 |
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| CN115721710A (zh) * | 2021-08-27 | 2023-03-03 | 康希诺生物股份公司 | 一种肺炎球菌结合疫苗组合物 |
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| WO2024110827A1 (en) * | 2022-11-21 | 2024-05-30 | Pfizer Inc. | Methods for preparing conjugated capsular saccharide antigens and uses thereof |
| EP4622665A2 (en) | 2022-11-22 | 2025-10-01 | Pfizer Inc. | Immunogenic compositions comprising conjugated capsular saccharide antigens and uses thereof |
| PE20252774A1 (es) | 2023-03-30 | 2025-12-22 | Pfizer | Composiciones inmunogenas que comprenden antigenos de sacarido capsular conjugados y usos de estos |
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| KR20260015203A (ko) | 2023-05-19 | 2026-02-02 | 글락소스미스클라인 바이오로지칼즈 에스.에이. | 호흡기 세포융합 바이러스 및 스트렙토코쿠스 뉴모니아에 감염에 대한 면역 반응을 유발하는 방법 |
| TW202527906A (zh) | 2023-09-14 | 2025-07-16 | 美商輝瑞股份有限公司 | 包含經結合之肺炎鏈球菌莢膜醣抗原之佐劑化致免疫性組成物及其用途 |
| WO2025186705A2 (en) | 2024-03-06 | 2025-09-12 | Pfizer Inc. | Immunogenic compositions comprising conjugated capsular saccharide antigens and uses thereof |
| CN120682395B (zh) * | 2025-08-20 | 2025-11-07 | 复星安特金(成都)生物制药有限公司 | 一种活化细菌荚膜多糖的方法 |
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