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 (enExample) | 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 (enExample) |
| EP (3) | EP3363806B1 (enExample) |
| JP (2) | JP6502262B2 (enExample) |
| KR (2) | KR101787217B1 (enExample) |
| CN (3) | CN104870463B (enExample) |
| AU (2) | AU2013365873B2 (enExample) |
| BR (2) | BR112015015031B1 (enExample) |
| CA (2) | CA2943263C (enExample) |
| DK (2) | DK2935299T3 (enExample) |
| ES (2) | ES2755082T3 (enExample) |
| FI (1) | FI3363806T3 (enExample) |
| FR (2) | FR22C1038I2 (enExample) |
| HR (1) | HRP20221438T1 (enExample) |
| HU (2) | HUE047120T2 (enExample) |
| IL (2) | IL274500B2 (enExample) |
| MX (2) | MX363512B (enExample) |
| PL (2) | PL3363806T3 (enExample) |
| PT (2) | PT2935299T (enExample) |
| RU (1) | RU2672053C2 (enExample) |
| SI (2) | SI3363806T1 (enExample) |
| WO (1) | WO2014097099A2 (enExample) |
Families Citing this family (58)
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| KR20220080201A (ko) | 2014-01-21 | 2022-06-14 | 화이자 인코포레이티드 | 접합된 캡슐 사카라이드 항원을 포함하는 면역원성 조성물 및 그의 용도 |
| 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 |
| CA2937190A1 (en) * | 2014-01-21 | 2015-07-30 | Pfizer Inc. | Streptococcus pneumoniae capsular polysaccharides and conjugates thereof |
| EP3148577B1 (en) | 2014-05-24 | 2021-01-20 | Biological E Limited | Novel semi-synthetic meningococcal conjugate vaccine |
| DK3244917T5 (da) | 2015-01-15 | 2024-10-14 | Pfizer | Immunogene sammensætninger til anvendelse i pneumokokvacciner |
| IL255106B2 (en) | 2015-05-04 | 2023-04-01 | Pfizer | Protein-polysaccharide conjugates of group b streptococcus, methods for preparing conjugates, immunogenic preparations containing conjugates and their uses |
| KR102800419B1 (ko) | 2015-07-21 | 2025-04-25 | 화이자 인코포레이티드 | 접합된 캡슐형 사카라이드 항원을 포함하는 면역원성 조성물, 그를 포함하는 키트 및 그의 용도 |
| KR20210011083A (ko) * | 2015-09-10 | 2021-01-29 | 인벤트프라이즈 엘엘씨 | 다가 vlp 접합체 |
| CA3005524C (en) | 2015-11-20 | 2023-10-10 | Pfizer Inc. | Immunogenic compositions for use in pneumococcal vaccines |
| 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 |
| KR20190044663A (ko) | 2016-09-02 | 2019-04-30 | 사노피 파스퇴르 인크 | 네이세리아 메닌기티디스 백신 |
| JP6944946B2 (ja) * | 2016-10-20 | 2021-10-06 | Ｋｍバイオロジクス株式会社 | 低分子化ＰＲＰを用いたＨｉｂコンジュゲートワクチンの製造方法 |
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| EP3824906A1 (en) | 2016-12-21 | 2021-05-26 | Amgen Inc. | Anti-tnf alpha antibody formulations |
| MX392525B (es) | 2017-01-20 | 2025-03-12 | Pfizer | Composiciones inmunogenicas para su uso en vacunas neumococicas |
| KR102650073B1 (ko) | 2017-01-31 | 2024-03-20 | 머크 샤프 앤드 돔 엘엘씨 | 스트렙토코커스 뉴모니아 혈청형 19f 유래의 협막 다당류 단백질 접합체의 제조 방법 |
| WO2018144439A1 (en) | 2017-01-31 | 2018-08-09 | Merck Sharp & Dohme Corp. | Methods for making polysaccharide-protein conjugates |
| BR112019017560A2 (pt) | 2017-02-24 | 2020-04-07 | Merck Sharp & Dohme | intensificação da imunogenicidade dos conjugados de polissacarídeo-proteína de streptococcus pneumoniae |
| US10729763B2 (en) | 2017-06-10 | 2020-08-04 | Inventprise, Llc | Mixtures of polysaccharide-protein pegylated compounds |
| CN111132691A (zh) | 2017-06-10 | 2020-05-08 | 创赏有限公司 | 提供改善的免疫原性和亲合力的具有二价或多价缀合物多糖的多价缀合物疫苗 |
| PT3678654T (pt) | 2017-09-07 | 2024-08-05 | Merck Sharp & Dohme Llc | Polissacáridos pneumocócicos e sua utilização em conjugados imunogénicos de polissacárido-proteína transportadora |
| US11389540B2 (en) | 2017-09-07 | 2022-07-19 | Merck Sharp & Dohme Llc | Pneumococcal polysaccharides and their use in immunogenic polysaccharide-carrier protein conjugates |
| CA3074703A1 (en) | 2017-09-07 | 2019-03-14 | Merck Sharp & Dohme Corp. | Pneumococcal polysaccharides and their use in immunogenic polysaccharide-carrier protein conjugates |
| MX2020005779A (es) | 2017-12-06 | 2020-10-28 | Merck Sharp & Dohme | Composiciones que comprenden conjugados de polisacarido de streptococcus pneumoniae con proteina y metodos de uso de estos. |
| 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 |
| AU2019239890B2 (en) * | 2018-03-23 | 2025-01-30 | Koranex Capital | Precision glycoconjugates as therapeutic tools |
| KR20210005158A (ko) | 2018-04-30 | 2021-01-13 | 머크 샤프 앤드 돔 코포레이션 | 스트렙토코쿠스 뉴모니아에 피막 폴리사카라이드 담체 단백질 접합체를 제조하는 방법 |
| JP7489324B2 (ja) | 2018-04-30 | 2024-05-23 | メルク・シャープ・アンド・ドーム・エルエルシー | リオスフィアから肺炎連鎖球菌莢膜多糖類キャリアタンパク質コンジュゲートを生産する方法 |
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| CN113164581A (zh) * | 2018-09-23 | 2021-07-23 | 生物E有限公司 | 纯化的肺炎链球菌荚膜多糖 |
| KR20240169145A (ko) | 2018-12-19 | 2024-12-02 | 머크 샤프 앤드 돔 엘엘씨 | 스트렙토코쿠스 뉴모니아에 폴리사카라이드-단백질 접합체를 포함하는 조성물 및 그의 사용 방법 |
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| CN110302375A (zh) * | 2019-06-27 | 2019-10-08 | 康希诺生物股份公司 | 一种糖缀合物及其用途 |
| US20230085173A1 (en) | 2020-02-21 | 2023-03-16 | Pfizer Inc. | Purification of saccharides |
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| CA3200968A1 (en) * | 2020-11-10 | 2022-05-19 | Pfizer Inc. | Immunogenic compositions comprising conjugated capsular saccharide antigens and uses thereof |
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