JP2008512494A5 - - Google Patents

Info

Publication number

JP2008512494A5

JP2008512494A5 JP2007531423A JP2007531423A JP2008512494A5 JP 2008512494 A5 JP2008512494 A5 JP 2008512494A5 JP 2007531423 A JP2007531423 A JP 2007531423A JP 2007531423 A JP2007531423 A JP 2007531423A JP 2008512494 A5 JP2008512494 A5 JP 2008512494A5

Authority

JP

Japan

Prior art keywords

mixture

polypeptides

tyrosine

acetic acid

acid

Prior art date

2005-09-09

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

Links

• Espacenet
• Global Dossier
• Discuss

• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 63
• 229920001184 polypeptide Polymers 0.000 claims 32
• 108090000765 processed proteins & peptides Proteins 0.000 claims 32
• 102000004196 processed proteins & peptides Human genes 0.000 claims 32
• 239000000203 mixture Substances 0.000 claims 30
• 238000000034 method Methods 0.000 claims 27
• BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims 22
• 239000000243 solution Substances 0.000 claims 17
• OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 claims 13
• 235000002374 tyrosine Nutrition 0.000 claims 13
• OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 claims 13
• QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims 12
• 235000004279 alanine Nutrition 0.000 claims 12
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 11
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 11
• 229910052794 bromium Inorganic materials 0.000 claims 11
• WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 claims 9
• 235000013922 glutamic acid Nutrition 0.000 claims 9
• 239000004220 glutamic acid Substances 0.000 claims 9
• WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims 8
• KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims 7
• 239000004472 Lysine Substances 0.000 claims 7
• 150000001413 amino acids Chemical group 0.000 claims 7
• 235000018977 lysine Nutrition 0.000 claims 7
• 239000008194 pharmaceutical composition Substances 0.000 claims 7
• 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 claims 7
• KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims 6
• 239000002516 radical scavenger Substances 0.000 claims 6
• 150000003668 tyrosines Chemical class 0.000 claims 6
• KNCHTBNNSQSLRV-YFKPBYRVSA-N (2s)-6-amino-2-[(2,2,2-trifluoroacetyl)amino]hexanoic acid Chemical compound NCCCC[C@@H](C(O)=O)NC(=O)C(F)(F)F KNCHTBNNSQSLRV-YFKPBYRVSA-N 0.000 claims 5
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 4
• 239000012535 impurity Substances 0.000 claims 4
• 229910021645 metal ion Inorganic materials 0.000 claims 3
• RLRYVSYUAHQYLS-QMMMGPOBSA-N (2s)-2-(bromoamino)-3-(4-hydroxyphenyl)propanoic acid Chemical compound OC(=O)[C@@H](NBr)CC1=CC=C(O)C=C1 RLRYVSYUAHQYLS-QMMMGPOBSA-N 0.000 claims 2
• ATCFYQUZTYQTJN-AXDSSHIGSA-N (2s)-2-amino-4-benzylpentanedioic acid Chemical compound OC(=O)[C@@H](N)CC(C(O)=O)CC1=CC=CC=C1 ATCFYQUZTYQTJN-AXDSSHIGSA-N 0.000 claims 2
• 241001550224 Apha Species 0.000 claims 2
• 108010072051 Glatiramer Acetate Proteins 0.000 claims 2
• FHEAIOHRHQGZPC-KIWGSFCNSA-N acetic acid;(2s)-2-amino-3-(4-hydroxyphenyl)propanoic acid;(2s)-2-aminopentanedioic acid;(2s)-2-aminopropanoic acid;(2s)-2,6-diaminohexanoic acid Chemical compound CC(O)=O.C[C@H](N)C(O)=O.NCCCC[C@H](N)C(O)=O.OC(=O)[C@@H](N)CCC(O)=O.OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 FHEAIOHRHQGZPC-KIWGSFCNSA-N 0.000 claims 2
• 239000007864 aqueous solution Substances 0.000 claims 2
• 229960003776 glatiramer acetate Drugs 0.000 claims 2
• 230000000379 polymerizing effect Effects 0.000 claims 2
• 239000012488 sample solution Substances 0.000 claims 2
• 239000002253 acid Substances 0.000 claims 1
• 235000001014 amino acid Nutrition 0.000 claims 1
• 238000004587 chromatography analysis Methods 0.000 claims 1
• 238000010511 deprotection reaction Methods 0.000 claims 1
• 229910052739 hydrogen Inorganic materials 0.000 claims 1
• 239000001257 hydrogen Substances 0.000 claims 1
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
• 230000003301 hydrolyzing effect Effects 0.000 claims 1
• 239000002184 metal Substances 0.000 claims 1
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 1
• 241000894007 species Species 0.000 claims 1
• 238000000108 ultra-filtration Methods 0.000 claims 1
• -1 γ-benzyl glutamate Chemical compound 0.000 claims 1