JP2010520855A5 - - Google Patents

Info

Publication number

JP2010520855A5

JP2010520855A5 JP2009548419A JP2009548419A JP2010520855A5 JP 2010520855 A5 JP2010520855 A5 JP 2010520855A5 JP 2009548419 A JP2009548419 A JP 2009548419A JP 2009548419 A JP2009548419 A JP 2009548419A JP 2010520855 A5 JP2010520855 A5 JP 2010520855A5

Authority

JP

Japan

Prior art keywords

integer

moiety

compound

peptide

linker

Prior art date

2008-01-30

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.)

Pending

Links

• Espacenet
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• 150000001875 compounds Chemical class 0.000 claims description 51
• 108090000765 processed proteins & peptides Proteins 0.000 claims description 41
• 239000000178 monomer Substances 0.000 claims description 7
• -1 linker moiety compound Chemical class 0.000 claims description 4
• 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 description 3
• 239000000203 mixture Substances 0.000 claims description 3
• 125000005647 linker group Chemical group 0.000 claims 23
• 229920003169 water-soluble polymer Chemical group 0.000 claims 17
• 229920001223 polyethylene glycol Polymers 0.000 claims 11
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical group OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 8
• 108010075944 Erythropoietin Receptors Proteins 0.000 claims 7
• 102100036509 Erythropoietin receptor Human genes 0.000 claims 7
• PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 claims 7
• 239000000539 dimer Substances 0.000 claims 6
• 239000002671 adjuvant Substances 0.000 claims 5
• 125000000217 alkyl group Chemical group 0.000 claims 5
• 239000000969 carrier Substances 0.000 claims 5
• 239000003085 diluting agent Substances 0.000 claims 5
• 239000003995 emulsifying agent Substances 0.000 claims 5
• 239000003755 preservative agent Substances 0.000 claims 5
• 239000002904 solvent Substances 0.000 claims 5
• 239000008194 pharmaceutical composition Substances 0.000 claims 4
• 239000002202 Polyethylene glycol Substances 0.000 claims 3
• 235000001014 amino acid Nutrition 0.000 claims 3
• 150000001413 amino acids Chemical class 0.000 claims 3
• 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 claims 3
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 3
• AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical compound C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 claims 3
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 3
• 125000001261 isocyanato group Chemical group *N=C=O 0.000 claims 3
• OKJIRPAQVSHGFK-UHFFFAOYSA-N N-acetylglycine Chemical compound CC(=O)NCC(O)=O OKJIRPAQVSHGFK-UHFFFAOYSA-N 0.000 claims 2
• 102000004196 processed proteins & peptides Human genes 0.000 claims 2
• FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 claims 2
• IYKLZBIWFXPUCS-VIFPVBQESA-N (2s)-2-(naphthalen-1-ylamino)propanoic acid Chemical compound C1=CC=C2C(N[C@@H](C)C(O)=O)=CC=CC2=C1 IYKLZBIWFXPUCS-VIFPVBQESA-N 0.000 claims 1
• 108010077895 Sarcosine Proteins 0.000 claims 1
• 235000018417 cysteine Nutrition 0.000 claims 1
• XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 claims 1
• SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 6
• 238000006471 dimerization reaction Methods 0.000 description 5
• 238000000034 method Methods 0.000 description 4
• 238000003776 cleavage reaction Methods 0.000 description 3
• 238000010647 peptide synthesis reaction Methods 0.000 description 3
• 230000007017 scission Effects 0.000 description 3
• 239000007858 starting material Substances 0.000 description 3
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
• 239000004471 Glycine Substances 0.000 description 2
• DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Natural products NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
• 229910004373 HOAc Inorganic materials 0.000 description 2
• 125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 description 2
• 230000006320 pegylation Effects 0.000 description 2
• 125000006239 protecting group Chemical group 0.000 description 2
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
• FMCAFXHLMUOIGG-IWFBPKFRSA-N (2s)-2-[[(2s)-2-[[(2s)-2-[[(2r)-2-formamido-3-sulfanylpropanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxy-2,5-dimethylphenyl)propanoyl]amino]-4-methylsulfanylbutanoic acid Chemical compound O=CN[C@@H](CS)C(=O)N[C@@H](C(C)C)C(=O)N[C@H](C(=O)N[C@@H](CCSC)C(O)=O)CC1=CC(C)=C(O)C=C1C FMCAFXHLMUOIGG-IWFBPKFRSA-N 0.000 description 1
• ZNUQQBSUOAMEBA-UHFFFAOYSA-N 2-(prop-2-enoxycarbonylamino)acetic acid Chemical compound OC(=O)CNC(=O)OCC=C ZNUQQBSUOAMEBA-UHFFFAOYSA-N 0.000 description 1
• BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
• 239000004472 Lysine Substances 0.000 description 1
• KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
• 210000004899 c-terminal region Anatomy 0.000 description 1
• 238000000746 purification Methods 0.000 description 1
• 239000011347 resin Substances 0.000 description 1
• 229920005989 resin Polymers 0.000 description 1
• 239000007787 solid Substances 0.000 description 1
• HNKJADCVZUBCPG-UHFFFAOYSA-N thioanisole Chemical compound CSC1=CC=CC=C1 HNKJADCVZUBCPG-UHFFFAOYSA-N 0.000 description 1
• ZGYICYBLPGRURT-UHFFFAOYSA-N tri(propan-2-yl)silicon Chemical compound CC(C)[Si](C(C)C)C(C)C ZGYICYBLPGRURT-UHFFFAOYSA-N 0.000 description 1