JP2018528928A5 - - Google Patents
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- Publication number
- JP2018528928A5 JP2018528928A5 JP2017567608A JP2017567608A JP2018528928A5 JP 2018528928 A5 JP2018528928 A5 JP 2018528928A5 JP 2017567608 A JP2017567608 A JP 2017567608A JP 2017567608 A JP2017567608 A JP 2017567608A JP 2018528928 A5 JP2018528928 A5 JP 2018528928A5
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- crystalline form
- side chain
- hydrogen
- 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.)
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- 238000000034 method Methods 0.000 claims 20
- 150000001875 compounds Chemical class 0.000 claims 18
- 239000000816 peptidomimetic Substances 0.000 claims 13
- 229910052739 hydrogen Inorganic materials 0.000 claims 8
- 239000001257 hydrogen Substances 0.000 claims 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 6
- 150000001413 amino acids Chemical class 0.000 claims 6
- 150000001923 cyclic compounds Chemical class 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 6
- -1 NR 9 Inorganic materials 0.000 claims 5
- 125000003118 aryl group Chemical group 0.000 claims 5
- 150000003840 hydrochlorides Chemical group 0.000 claims 5
- 125000006239 protecting group Chemical group 0.000 claims 5
- 239000000243 solution Substances 0.000 claims 5
- 125000001424 substituent group Chemical group 0.000 claims 5
- 239000004475 Arginine Substances 0.000 claims 4
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 claims 4
- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 claims 4
- 229940024606 amino acid Drugs 0.000 claims 4
- 235000001014 amino acid Nutrition 0.000 claims 4
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims 4
- 150000002431 hydrogen Chemical class 0.000 claims 4
- 229960000310 isoleucine Drugs 0.000 claims 4
- AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 claims 4
- 239000000203 mixture Substances 0.000 claims 4
- 238000007363 ring formation reaction Methods 0.000 claims 4
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims 3
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims 3
- 239000004472 Lysine Substances 0.000 claims 3
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims 3
- 235000013922 glutamic acid Nutrition 0.000 claims 3
- 239000004220 glutamic acid Substances 0.000 claims 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Natural products OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 claims 2
- DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 claims 2
- AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 claims 2
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 claims 2
- 239000004473 Threonine Substances 0.000 claims 2
- 230000002378 acidificating effect Effects 0.000 claims 2
- 229960001230 asparagine Drugs 0.000 claims 2
- 235000009582 asparagine Nutrition 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
- 229960002989 glutamic acid Drugs 0.000 claims 2
- 239000000543 intermediate Substances 0.000 claims 2
- 235000014705 isoleucine Nutrition 0.000 claims 2
- 229960003646 lysine Drugs 0.000 claims 2
- 235000018977 lysine Nutrition 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 238000002156 mixing Methods 0.000 claims 2
- 238000010534 nucleophilic substitution reaction Methods 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 238000000634 powder X-ray diffraction Methods 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical compound C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 claims 2
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 claims 2
- 229960004441 tyrosine Drugs 0.000 claims 2
- 235000002374 tyrosine Nutrition 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 1
- 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 claims 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 150000001343 alkyl silanes Chemical class 0.000 claims 1
- 239000002585 base Substances 0.000 claims 1
- 239000003637 basic solution Substances 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 239000013078 crystal Substances 0.000 claims 1
- 238000002425 crystallisation Methods 0.000 claims 1
- 230000008025 crystallization Effects 0.000 claims 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 1
- 125000000524 functional group Chemical group 0.000 claims 1
- 230000001788 irregular Effects 0.000 claims 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims 1
- 229910052698 phosphorus Inorganic materials 0.000 claims 1
- 239000003880 polar aprotic solvent Substances 0.000 claims 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims 1
- 125000006413 ring segment Chemical group 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 claims 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562190596P | 2015-07-09 | 2015-07-09 | |
| US62/190,596 | 2015-07-09 | ||
| PCT/EP2016/066281 WO2017005902A1 (en) | 2015-07-09 | 2016-07-08 | Solution phase synthesis and crystallization of beta-turn peptidomimetic cyclic salts |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2018528928A JP2018528928A (ja) | 2018-10-04 |
| JP2018528928A5 true JP2018528928A5 (OSRAM) | 2019-04-18 |
| JP6801835B2 JP6801835B2 (ja) | 2020-12-16 |
Family
ID=56413639
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017567608A Active JP6801835B2 (ja) | 2015-07-09 | 2016-07-08 | β−ターンペプチド模倣環状塩の液相合成及び結晶化 |
Country Status (9)
| Country | Link |
|---|---|
| US (4) | US10125165B2 (OSRAM) |
| EP (2) | EP3319978B1 (OSRAM) |
| JP (1) | JP6801835B2 (OSRAM) |
| KR (1) | KR102056257B1 (OSRAM) |
| CN (2) | CN114874288A (OSRAM) |
| AU (1) | AU2016290654C1 (OSRAM) |
| CA (1) | CA2991661A1 (OSRAM) |
| TW (1) | TWI708779B (OSRAM) |
| WO (1) | WO2017005902A1 (OSRAM) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6801835B2 (ja) | 2015-07-09 | 2020-12-16 | ミメトゲン ファーマシュウティカルズ インコーポレイテッドＭｉｍｅｔｏｇｅｎ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ， Ｉｎｃ． | β−ターンペプチド模倣環状塩の液相合成及び結晶化 |
| PL3464336T3 (pl) | 2016-06-01 | 2022-05-16 | Athira Pharma, Inc. | Związki |
| MX2020012629A (es) * | 2018-05-31 | 2021-01-29 | Sederma Sa | Metodo para sintesis de peptido en fase de solucion y estrategias protectoras de la misma. |
| US11427612B2 (en) * | 2018-08-21 | 2022-08-30 | Wayne State University | Epimerization-free N to C solid-phase peptide synthesis |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AUPP254898A0 (en) * | 1998-03-24 | 1998-04-23 | University Of Queensland, The | Peptide turn mimetics |
| WO2001052843A1 (en) | 2000-01-18 | 2001-07-26 | Mcgill University | β-TURN PEPTIDOMIMETIC CYCLIC COMPOUNDS |
| BR0311558A (pt) * | 2002-06-11 | 2007-04-27 | Lilly Co Eli | composto ou sal farmaceuticamente aceitável do mesmo, processo para preparar o mesmo, métodos para afetar os receptores de glutamato metabotrópicos ligados a camp, para administrar uma quantidade eficaz de um composto e para tratar um distúrbio neurológico e psiquiátrico em um paciente, e, formulação farmacêutica |
| KR101565185B1 (ko) * | 2008-04-04 | 2015-11-02 | 미메토젠 파르마슈티칼스 인크. | 건안증을 치료하기 위한 베타-턴 펩티도미메틱 환상 화합물 |
| ES2512717T3 (es) * | 2009-02-27 | 2014-10-24 | Mimetogen Pharmaceuticals Inc. | Compuestos cíclicos peptidomiméticos para el tratamiento de la retinitis pigmentosa |
| WO2012013281A1 (de) * | 2010-07-29 | 2012-02-02 | Merck Patent Gmbh | Flüssigkristallines medium enthaltend thiophenderivate |
| JP5710436B2 (ja) * | 2011-09-26 | 2015-04-30 | 株式会社東芝 | パターン形成方法 |
| KR102061382B1 (ko) * | 2012-06-22 | 2019-12-31 | 미메토젠 파르마슈티칼스 인크. | 베타-턴 펩티도미메틱 환상 화합물의 합성 |
| JP6516974B2 (ja) * | 2013-06-14 | 2019-05-22 | 豊田合成株式会社 | ゴム組成物及びゴム製品 |
| US9200100B2 (en) * | 2013-06-20 | 2015-12-01 | Exxonmobil Chemical Patents Inc. | Long-bridged salen catalyst |
| JP6801835B2 (ja) * | 2015-07-09 | 2020-12-16 | ミメトゲン ファーマシュウティカルズ インコーポレイテッドＭｉｍｅｔｏｇｅｎ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ， Ｉｎｃ． | β−ターンペプチド模倣環状塩の液相合成及び結晶化 |
-
2016
- 2016-07-08 JP JP2017567608A patent/JP6801835B2/ja active Active
- 2016-07-08 KR KR1020187003965A patent/KR102056257B1/ko active Active
- 2016-07-08 CN CN202210654769.XA patent/CN114874288A/zh active Pending
- 2016-07-08 CA CA2991661A patent/CA2991661A1/en active Pending
- 2016-07-08 CN CN201680040450.0A patent/CN107849089B/zh active Active
- 2016-07-08 EP EP16739073.1A patent/EP3319978B1/en active Active
- 2016-07-08 AU AU2016290654A patent/AU2016290654C1/en active Active
- 2016-07-08 EP EP25158656.6A patent/EP4549450A3/en active Pending
- 2016-07-08 US US15/205,909 patent/US10125165B2/en active Active
- 2016-07-08 WO PCT/EP2016/066281 patent/WO2017005902A1/en not_active Ceased
- 2016-07-11 TW TW105121814A patent/TWI708779B/zh active
-
2018
- 2018-11-08 US US16/184,485 patent/US11078234B2/en active Active
-
2021
- 2021-06-02 US US17/337,383 patent/US11753441B2/en active Active
-
2023
- 2023-07-18 US US18/354,076 patent/US12281179B2/en active Active
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