JP2018505152A5 - - Google Patents
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- JP2018505152A5 JP2018505152A5 JP2017534727A JP2017534727A JP2018505152A5 JP 2018505152 A5 JP2018505152 A5 JP 2018505152A5 JP 2017534727 A JP2017534727 A JP 2017534727A JP 2017534727 A JP2017534727 A JP 2017534727A JP 2018505152 A5 JP2018505152 A5 JP 2018505152A5
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- amino acid
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- 108090000765 processed proteins & peptides Proteins 0.000 claims description 45
- 150000001875 compounds Chemical class 0.000 claims description 17
- 101001136981 Homo sapiens Proteasome subunit beta type-9 Proteins 0.000 claims description 8
- 102100035764 Proteasome subunit beta type-9 Human genes 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 5
- 102000004196 processed proteins & peptides Human genes 0.000 claims description 5
- 239000000863 peptide conjugate Substances 0.000 claims description 4
- 150000003573 thiols Chemical class 0.000 claims description 4
- 125000000539 amino acid group Chemical group 0.000 claims 17
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 12
- 229910052739 hydrogen Inorganic materials 0.000 claims 10
- 239000001257 hydrogen Substances 0.000 claims 10
- 150000001413 amino acids Chemical class 0.000 claims 9
- 125000000217 alkyl group Chemical group 0.000 claims 8
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 5
- 150000002431 hydrogen Chemical class 0.000 claims 5
- 150000003839 salts Chemical class 0.000 claims 5
- 125000003275 alpha amino acid group Chemical group 0.000 claims 4
- 239000002131 composite material Substances 0.000 claims 4
- 239000012453 solvate Substances 0.000 claims 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- 150000002632 lipids Chemical class 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 125000006239 protecting group Chemical group 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 claims 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims 2
- 239000000562 conjugate Substances 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 125000004404 heteroalkyl group Chemical group 0.000 claims 2
- 230000028993 immune response Effects 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 1
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 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
- 230000003381 solubilizing effect Effects 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
- 239000011347 resin Substances 0.000 description 22
- 229920005989 resin Polymers 0.000 description 22
- 239000000203 mixture Substances 0.000 description 9
- 238000003776 cleavage reaction Methods 0.000 description 8
- 230000007017 scission Effects 0.000 description 8
- 238000006596 Alder-ene reaction Methods 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
- FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 description 6
- 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- UJRIYYLGNDXVTA-UHFFFAOYSA-N ethenyl hexadecanoate Chemical compound CCCCCCCCCCCCCCCC(=O)OC=C UJRIYYLGNDXVTA-UHFFFAOYSA-N 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- OXBLVCZKDOZZOJ-UHFFFAOYSA-N 2,3-Dihydrothiophene Chemical compound C1CC=CS1 OXBLVCZKDOZZOJ-UHFFFAOYSA-N 0.000 description 4
- BWZVCCNYKMEVEX-UHFFFAOYSA-N 2,4,6-Trimethylpyridine Chemical compound CC1=CC(C)=NC(C)=C1 BWZVCCNYKMEVEX-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 4
- HCZMHWVFVZAHCR-UHFFFAOYSA-N 2-[2-(2-sulfanylethoxy)ethoxy]ethanethiol Chemical compound SCCOCCOCCS HCZMHWVFVZAHCR-UHFFFAOYSA-N 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000010511 deprotection reaction Methods 0.000 description 3
- 238000004949 mass spectrometry Methods 0.000 description 3
- PSGAAPLEWMOORI-PEINSRQWSA-N medroxyprogesterone acetate Chemical compound C([C@@]12C)CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2CC[C@]2(C)[C@@](OC(C)=O)(C(C)=O)CC[C@H]21 PSGAAPLEWMOORI-PEINSRQWSA-N 0.000 description 3
- 239000008188 pellet Substances 0.000 description 3
- 238000004007 reversed phase HPLC Methods 0.000 description 3
- 239000006228 supernatant Substances 0.000 description 3
- KLBPUVPNPAJWHZ-UMSFTDKQSA-N (2r)-2-(9h-fluoren-9-ylmethoxycarbonylamino)-3-tritylsulfanylpropanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)OCC1C2=CC=CC=C2C2=CC=CC=C21)SC(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 KLBPUVPNPAJWHZ-UMSFTDKQSA-N 0.000 description 2
- AUHZEENZYGFFBQ-UHFFFAOYSA-N 1,3,5-Me3C6H3 Natural products CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
- 238000006640 acetylation reaction Methods 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000004108 freeze drying Methods 0.000 description 2
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 2
- QTUVCTXXMOZFHS-UHFFFAOYSA-N N-(8-aminooctyl)-2-[2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-4-yl]oxyacetamide Chemical compound NCCCCCCCCNC(=O)COC1=CC=CC2=C1C(=O)N(C1CCC(=O)NC1=O)C2=O QTUVCTXXMOZFHS-UHFFFAOYSA-N 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 101100364827 Prochlorococcus marinus (strain SARG / CCMP1375 / SS120) ahcY gene Proteins 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 235000019439 ethyl acetate Nutrition 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000001360 methionine group Chemical group N[C@@H](CCSC)C(=O)* 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-N n-hexadecanoic acid Natural products CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201462096106P | 2014-12-23 | 2014-12-23 | |
| US62/096,106 | 2014-12-23 | ||
| PCT/IB2015/059901 WO2016103192A1 (en) | 2014-12-23 | 2015-12-22 | Amino acid and peptide conjugates and uses thereof |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2021000444A Division JP2021073199A (ja) | 2014-12-23 | 2021-01-05 | アミノ酸複合体及びペプチド複合体ならびにそれらの使用 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2018505152A JP2018505152A (ja) | 2018-02-22 |
| JP2018505152A5 true JP2018505152A5 (https=) | 2019-02-07 |
Family
ID=56149361
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017534727A Pending JP2018505152A (ja) | 2014-12-23 | 2015-12-22 | アミノ酸複合体及びペプチド複合体ならびにそれらの使用 |
| JP2021000444A Pending JP2021073199A (ja) | 2014-12-23 | 2021-01-05 | アミノ酸複合体及びペプチド複合体ならびにそれらの使用 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2021000444A Pending JP2021073199A (ja) | 2014-12-23 | 2021-01-05 | アミノ酸複合体及びペプチド複合体ならびにそれらの使用 |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US10253062B2 (https=) |
| EP (1) | EP3237374A4 (https=) |
| JP (2) | JP2018505152A (https=) |
| KR (1) | KR20170094449A (https=) |
| CN (1) | CN107250103A (https=) |
| AU (2) | AU2015370479B2 (https=) |
| BR (1) | BR112017013574A2 (https=) |
| CA (1) | CA2971677A1 (https=) |
| IL (1) | IL252902A0 (https=) |
| MX (1) | MX2017008406A (https=) |
| RU (1) | RU2017126206A (https=) |
| SG (1) | SG11201704962WA (https=) |
| WO (1) | WO2016103192A1 (https=) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK2576638T3 (da) * | 2010-05-25 | 2021-03-15 | Syndevrx Inc | Polymerkonjugerede metap2-inhibitorer og terapeutiske fremgangsmåder til anvendelse deraf |
| CN105431426A (zh) | 2013-04-10 | 2016-03-23 | 新德发制药有限公司 | Metap2抑制剂和治疗肥胖症的方法 |
| WO2014207708A2 (en) | 2013-06-28 | 2014-12-31 | Auckland Uniservices Limited | Amino acid and peptide conjugates and conjugation process |
| BR112017013574A2 (pt) | 2014-12-23 | 2018-03-06 | Verdon Daniel | conjugados de aminoácido e peptídeo e usos dos mesmos |
| EP3419962A4 (en) | 2016-02-26 | 2020-03-11 | Auckland Uniservices Limited | CONJUGATES OF AMINO ACIDS AND PEPTIDES AND CONJUGATION METHOD |
| NL2018803B1 (en) * | 2017-04-27 | 2018-11-05 | Academisch Ziekenhuis Leiden Handelend Onder De Naam Leids Univ Medisch Centrum/ H O D N Lumc | Adjuvant compounds |
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-
2015
- 2015-12-22 BR BR112017013574A patent/BR112017013574A2/pt not_active Application Discontinuation
- 2015-12-22 CA CA2971677A patent/CA2971677A1/en not_active Abandoned
- 2015-12-22 CN CN201580076680.8A patent/CN107250103A/zh active Pending
- 2015-12-22 JP JP2017534727A patent/JP2018505152A/ja active Pending
- 2015-12-22 EP EP15872074.8A patent/EP3237374A4/en not_active Withdrawn
- 2015-12-22 SG SG11201704962WA patent/SG11201704962WA/en unknown
- 2015-12-22 WO PCT/IB2015/059901 patent/WO2016103192A1/en not_active Ceased
- 2015-12-22 KR KR1020177020221A patent/KR20170094449A/ko not_active Ceased
- 2015-12-22 MX MX2017008406A patent/MX2017008406A/es unknown
- 2015-12-22 AU AU2015370479A patent/AU2015370479B2/en not_active Ceased
- 2015-12-22 US US15/535,956 patent/US10253062B2/en active Active
- 2015-12-22 RU RU2017126206A patent/RU2017126206A/ru not_active Application Discontinuation
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2017
- 2017-06-14 IL IL252902A patent/IL252902A0/en unknown
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2019
- 2019-01-18 US US16/251,136 patent/US11014960B2/en not_active Expired - Fee Related
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2020
- 2020-10-16 AU AU2020256429A patent/AU2020256429A1/en not_active Abandoned
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2021
- 2021-01-05 JP JP2021000444A patent/JP2021073199A/ja active Pending
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