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) | EP3363806B1 (https=) |
| JP (2) | JP6502262B2 (https=) |
| KR (2) | KR101787217B1 (https=) |
| CN (3) | CN108524931B (https=) |
| AU (2) | AU2013365873B2 (https=) |
| BR (2) | BR112015015031B1 (https=) |
| CA (2) | CA2893343C (https=) |
| DK (2) | DK3363806T3 (https=) |
| ES (2) | ES2755082T3 (https=) |
| FI (1) | FI3363806T3 (https=) |
| FR (2) | FR22C1038I2 (https=) |
| HR (1) | HRP20221438T1 (https=) |
| HU (2) | HUE060718T2 (https=) |
| IL (2) | IL274500B2 (https=) |
| MX (2) | MX379386B (https=) |
| PL (2) | PL2935299T3 (https=) |
| PT (2) | PT3363806T (https=) |
| RU (1) | RU2672053C2 (https=) |
| SI (2) | SI2935299T1 (https=) |
| WO (1) | WO2014097099A2 (https=) |
Families Citing this family (58)
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| IL312327B2 (en) | 2014-01-21 | 2026-02-01 | Pfizer | Immunogenic preparations comprising conjugated capsular saccharide antigens and their uses |
| US11160855B2 (en) | 2014-01-21 | 2021-11-02 | Pfizer Inc. | Immunogenic compositions comprising conjugated capsular saccharide antigens and uses thereof |
| CN120718167A (zh) | 2014-01-21 | 2025-09-30 | 辉瑞大药厂 | 肺炎链球菌荚膜多糖及其缀合物 |
| BR112016016580B1 (pt) * | 2014-01-21 | 2024-01-09 | Pfizer Inc | Processo para a preparação de um conjugado imunogênico, conjugado imunogênico, composição imunogênica, e vacina |
| EP3148577B1 (en) | 2014-05-24 | 2021-01-20 | Biological E Limited | Novel semi-synthetic meningococcal conjugate vaccine |
| CN107427568B (zh) | 2015-01-15 | 2021-12-14 | 辉瑞公司 | 用于肺炎球菌疫苗中的免疫原性组合物 |
| PE20220774A1 (es) | 2015-05-04 | 2022-05-16 | Pfizer | Conjugados proteina-polisacarido de estreptococo grupo b, metodos para producir conjugados, composiciones inmunogenas que comprenden conjugados y sus usos |
| CN108367063A (zh) * | 2015-07-21 | 2018-08-03 | 辉瑞公司 | 包含缀合的荚膜糖抗原的免疫原性组合物及其试剂盒和用途 |
| PH12018500305B1 (en) * | 2015-09-10 | 2023-03-15 | Inventprise Llc | Multivalent vlp conjugates |
| 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 |
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| WO2018119142A1 (en) | 2016-12-21 | 2018-06-28 | Amgen Inc. | Anti-tnf alpha antibody formulations |
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| CN110225764A (zh) | 2017-01-31 | 2019-09-10 | 默沙东公司 | 制备多糖-蛋白缀合物的方法 |
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| CN111065387B (zh) | 2017-09-07 | 2023-08-25 | 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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