JP2017532329A5 - - Google Patents
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- Publication number
- JP2017532329A5 JP2017532329A5 JP2017518431A JP2017518431A JP2017532329A5 JP 2017532329 A5 JP2017532329 A5 JP 2017532329A5 JP 2017518431 A JP2017518431 A JP 2017518431A JP 2017518431 A JP2017518431 A JP 2017518431A JP 2017532329 A5 JP2017532329 A5 JP 2017532329A5
- Authority
- JP
- Japan
- Prior art keywords
- substituted
- alkyl
- solvent
- alken
- unsubstituted aryl
- 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
Links
- 238000000034 method Methods 0.000 claims description 112
- 150000001875 compounds Chemical class 0.000 claims description 106
- 125000003118 aryl group Chemical group 0.000 claims description 74
- -1 2-propen-1-yl Chemical group 0.000 claims description 54
- 239000002904 solvent Substances 0.000 claims description 51
- 125000000217 alkyl group Chemical group 0.000 claims description 37
- 239000000203 mixture Substances 0.000 claims description 36
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 32
- 239000003880 polar aprotic solvent Substances 0.000 claims description 25
- 239000003586 protic polar solvent Substances 0.000 claims description 16
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- 125000005604 azodicarboxylate group Chemical group 0.000 claims description 14
- 150000004820 halides Chemical class 0.000 claims description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 11
- 239000003153 chemical reaction reagent Substances 0.000 claims description 11
- GPKUICFDWYEPTK-UHFFFAOYSA-N methoxycyclohexatriene Chemical compound COC1=CC=C=C[CH]1 GPKUICFDWYEPTK-UHFFFAOYSA-N 0.000 claims description 8
- 125000003232 p-nitrobenzoyl group Chemical group [N+](=O)([O-])C1=CC=C(C(=O)*)C=C1 0.000 claims description 8
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 7
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 239000000010 aprotic solvent Substances 0.000 claims description 5
- 239000003446 ligand Substances 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- 150000001540 azides Chemical class 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 239000007848 Bronsted acid Substances 0.000 claims description 3
- 150000004673 fluoride salts Chemical class 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000005207 tetraalkylammonium group Chemical group 0.000 claims description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 40
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 33
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 20
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 0 C[C@](C([C@@](C([C@](C)O[C@](C[C@@](C([C@](C1)O)C(O)=O)OC1(CC(C1)OC(*)OC1C(CCC(C1)OC(*)OC1CC(O[C@@](C)[C@@]1C)=O)O)OC)C=CC=CC=CC=CC=CC=CC=C[C@](*)C1O)O)N)O)O Chemical compound C[C@](C([C@@](C([C@](C)O[C@](C[C@@](C([C@](C1)O)C(O)=O)OC1(CC(C1)OC(*)OC1C(CCC(C1)OC(*)OC1CC(O[C@@](C)[C@@]1C)=O)O)OC)C=CC=CC=CC=CC=CC=CC=C[C@](*)C1O)O)N)O)O 0.000 description 3
- NBOMNTLFRHMDEZ-UHFFFAOYSA-N thiosalicylic acid Chemical group OC(=O)C1=CC=CC=C1S NBOMNTLFRHMDEZ-UHFFFAOYSA-N 0.000 description 3
- 229940103494 thiosalicylic acid Drugs 0.000 description 3
- WNLMYNASWOULQY-UHFFFAOYSA-N 4-tert-butylbenzoyl chloride Chemical compound CC(C)(C)C1=CC=C(C(Cl)=O)C=C1 WNLMYNASWOULQY-UHFFFAOYSA-N 0.000 description 2
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- GRJJQCWNZGRKAU-UHFFFAOYSA-N pyridin-1-ium;fluoride Chemical group F.C1=CC=NC=C1 GRJJQCWNZGRKAU-UHFFFAOYSA-N 0.000 description 2
- YFMMNRNSTUPXBU-FLCNYULVSA-N C[C@H]([C@H]([C@@H]([C@H]1O)N)O)OC1OC(C[C@@H]([C@@H]([C@H](C1)O)C(O)=O)OC1(CC(CC(C(CCC(CC(CC(O[C@@H](C)C1)=O)O)O)O)O)O)O)/C=C\C=C/C=C\C=C/C=C\C=C/C=C\[C@H](C)[C@H]1O Chemical compound C[C@H]([C@H]([C@@H]([C@H]1O)N)O)OC1OC(C[C@@H]([C@@H]([C@H](C1)O)C(O)=O)OC1(CC(CC(C(CCC(CC(CC(O[C@@H](C)C1)=O)O)O)O)O)O)O)/C=C\C=C/C=C\C=C/C=C\C=C/C=C\[C@H](C)[C@H]1O YFMMNRNSTUPXBU-FLCNYULVSA-N 0.000 description 1
- RIXRWPWLOMOUPT-UHFFFAOYSA-N [diethyl(propan-2-yl)silyl] trifluoromethanesulfonate Chemical compound CC[Si](CC)(C(C)C)OS(=O)(=O)C(F)(F)F RIXRWPWLOMOUPT-UHFFFAOYSA-N 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201462065330P | 2014-10-17 | 2014-10-17 | |
| US62/065,330 | 2014-10-17 | ||
| PCT/US2015/055899 WO2016061437A1 (en) | 2014-10-17 | 2015-10-16 | Scalable synthesis of reduced toxicity derivative of amphotericin b |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2017532329A JP2017532329A (ja) | 2017-11-02 |
| JP2017532329A5 true JP2017532329A5 (enExample) | 2018-11-22 |
| JP6755859B2 JP6755859B2 (ja) | 2020-09-16 |
Family
ID=55747385
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017518431A Active JP6755859B2 (ja) | 2014-10-17 | 2015-10-16 | アムホテリシンｂの毒性が低減された誘導体の規模変更可能な合成法 |
Country Status (5)
| Country | Link |
|---|---|
| US (2) | US10087206B2 (enExample) |
| EP (1) | EP3206695A4 (enExample) |
| JP (1) | JP6755859B2 (enExample) |
| AU (2) | AU2015331904B2 (enExample) |
| WO (1) | WO2016061437A1 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9738677B2 (en) * | 2014-05-16 | 2017-08-22 | The Board Of Trustees Of The University Of Illinois | Amphotericin B derivative with reduced toxicity |
| AU2015331904B2 (en) * | 2014-10-17 | 2021-02-11 | The Board Of Trustees Of The University Of Illinois | Scalable synthesis of reduced toxicity derivative of amphotericin B |
| EP3283171B1 (en) | 2015-04-15 | 2021-05-26 | Sfunga Therapeutics, Inc. | Derivatives of amphotericin b |
| US20230000891A1 (en) * | 2019-08-08 | 2023-01-05 | The Board Of Trustees Of The University Of Illinois | Hybrid amphotericin b derivatives with reduced toxicity |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1008720A (en) | 1910-11-14 | 1911-11-14 | John Knape | Adjustable bracket. |
| EP0431874A1 (en) | 1989-12-08 | 1991-06-12 | Beecham Group p.l.c. | Novel compounds |
| EP2371815A1 (en) * | 2003-12-30 | 2011-10-05 | XenoPort, Inc. | Sythesis of acyloxyalkyl carbamate prodrugs and intermediates thereof |
| WO2014059436A1 (en) * | 2012-10-12 | 2014-04-17 | The Board Of Trustees Of The University Of Illinois | Electronic tuning of site selectivity |
| WO2014165676A1 (en) * | 2013-04-03 | 2014-10-09 | The Board Of Trustees Of The University Of Illinois | Amphotericin b derivative with reduced toxicity |
| US9738677B2 (en) * | 2014-05-16 | 2017-08-22 | The Board Of Trustees Of The University Of Illinois | Amphotericin B derivative with reduced toxicity |
| MA39568A1 (fr) * | 2014-06-12 | 2017-09-29 | Shionogi & Co | Dérivé de macrolide de polyène |
| AU2015331904B2 (en) * | 2014-10-17 | 2021-02-11 | The Board Of Trustees Of The University Of Illinois | Scalable synthesis of reduced toxicity derivative of amphotericin B |
-
2015
- 2015-10-16 AU AU2015331904A patent/AU2015331904B2/en active Active
- 2015-10-16 EP EP15851160.0A patent/EP3206695A4/en active Pending
- 2015-10-16 JP JP2017518431A patent/JP6755859B2/ja active Active
- 2015-10-16 WO PCT/US2015/055899 patent/WO2016061437A1/en not_active Ceased
- 2015-10-16 US US15/519,471 patent/US10087206B2/en active Active
-
2018
- 2018-10-01 US US16/148,255 patent/US10683318B2/en active Active
-
2021
- 2021-05-10 AU AU2021202949A patent/AU2021202949B2/en active Active
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