JP2020514373A5 - - Google Patents
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- JP2020514373A5 JP2020514373A5 JP2019551278A JP2019551278A JP2020514373A5 JP 2020514373 A5 JP2020514373 A5 JP 2020514373A5 JP 2019551278 A JP2019551278 A JP 2019551278A JP 2019551278 A JP2019551278 A JP 2019551278A JP 2020514373 A5 JP2020514373 A5 JP 2020514373A5
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- JP
- Japan
- Prior art keywords
- formula
- compound represented
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- protecting
- group
- 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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- 150000001875 compounds Chemical class 0.000 claims description 77
- 238000000034 method Methods 0.000 claims description 68
- 125000003277 amino group Chemical group 0.000 claims description 47
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 31
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- 239000001257 hydrogen Substances 0.000 claims description 24
- 150000002431 hydrogen Chemical class 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- PYMYPHUHKUWMLA-LMVFSUKVSA-N aldehydo-D-ribose Chemical compound OC[C@@H](O)[C@@H](O)[C@@H](O)C=O PYMYPHUHKUWMLA-LMVFSUKVSA-N 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 11
- 125000002252 acyl group Chemical group 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- 239000012458 free base Substances 0.000 claims description 9
- GSYSFVSGPABNNL-UHFFFAOYSA-N methyl 2-dimethoxyphosphoryl-2-(phenylmethoxycarbonylamino)acetate Chemical group COC(=O)C(P(=O)(OC)OC)NC(=O)OCC1=CC=CC=C1 GSYSFVSGPABNNL-UHFFFAOYSA-N 0.000 claims description 9
- 230000008878 coupling Effects 0.000 claims description 8
- 238000010168 coupling process Methods 0.000 claims description 8
- 238000005859 coupling reaction Methods 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- -1 (CBz) -protected amino group Chemical group 0.000 claims description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 6
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 claims description 6
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 5
- 238000010511 deprotection reaction Methods 0.000 claims description 5
- 239000007818 Grignard reagent Substances 0.000 claims description 4
- 150000001299 aldehydes Chemical class 0.000 claims description 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
- 150000004795 grignard reagents Chemical class 0.000 claims description 4
- 229940126575 aminoglycoside Drugs 0.000 claims description 3
- 229910021529 ammonia Inorganic materials 0.000 claims description 3
- 238000011065 in-situ storage Methods 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 230000001681 protective effect Effects 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- YSNXOQGDHGUKCZ-UHFFFAOYSA-N n-benzylhydroxylamine;hydron;chloride Chemical compound Cl.ONCC1=CC=CC=C1 YSNXOQGDHGUKCZ-UHFFFAOYSA-N 0.000 claims description 2
- 238000005580 one pot reaction Methods 0.000 claims description 2
- 230000001590 oxidative effect Effects 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 2
- UHEPSJJJMTWUCP-DHDYTCSHSA-N (2r,3r,4r,5r)-2-[(1s,2s,3r,4s,6r)-4,6-diamino-3-[(2s,3r,4r,5s,6r)-3-amino-4,5-dihydroxy-6-[(1r)-1-hydroxyethyl]oxan-2-yl]oxy-2-hydroxycyclohexyl]oxy-5-methyl-4-(methylamino)oxane-3,5-diol;sulfuric acid Chemical compound OS(O)(=O)=O.OS(O)(=O)=O.O1C[C@@](O)(C)[C@H](NC)[C@@H](O)[C@H]1O[C@@H]1[C@@H](O)[C@H](O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H]([C@@H](C)O)O2)N)[C@@H](N)C[C@H]1N UHEPSJJJMTWUCP-DHDYTCSHSA-N 0.000 description 2
- 0 *[C@](C([C@](C(C1N)O)O)O[C@@]1O[C@](C(C[C@](C1O)N*)N)C1O)O Chemical compound *[C@](C([C@](C(C1N)O)O)O[C@@]1O[C@](C(C[C@](C1O)N*)N)C1O)O 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN201721008996 | 2017-03-15 | ||
| IN201721008996 | 2017-03-15 | ||
| PCT/IL2018/050306 WO2018167794A1 (en) | 2017-03-15 | 2018-03-15 | Large scale preparation of pseudo-trisaccharide aminoglycosides and of intermediates thereof |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2020514373A JP2020514373A (ja) | 2020-05-21 |
| JP2020514373A5 true JP2020514373A5 (https=) | 2021-04-30 |
| JP7187471B2 JP7187471B2 (ja) | 2022-12-12 |
Family
ID=63521924
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019551278A Active JP7187471B2 (ja) | 2017-03-15 | 2018-03-15 | 擬似三糖アミノグリコシドおよびその中間体の大規模調製 |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US11136345B2 (https=) |
| EP (1) | EP3609902A4 (https=) |
| JP (1) | JP7187471B2 (https=) |
| CN (2) | CN117466958A (https=) |
| AU (2) | AU2018235441C1 (https=) |
| BR (1) | BR112019018834A2 (https=) |
| CA (1) | CA3055883A1 (https=) |
| IL (1) | IL269364B (https=) |
| WO (1) | WO2018167794A1 (https=) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2021061873A1 (en) * | 2019-09-23 | 2021-04-01 | Eloxx Pharmaceuticals, Inc. | Methods, compositions, and kits for treating polycystic kidney disease |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3897412A (en) | 1972-05-04 | 1975-07-29 | Bristol Myers Co | Paromomycin antibiotic derivatives |
| US4024332A (en) | 1973-06-05 | 1977-05-17 | Pfizer Inc. | Aminoglycoside antibiotics and intermediates therefor |
| US4029882A (en) | 1974-03-19 | 1977-06-14 | Schering Corporation | Selective acylation of the C-1 amino group of aminoglycoside antibiotics |
| US3996205A (en) | 1975-09-08 | 1976-12-07 | The Upjohn Company | Aminoglycoside antibiotics and intermediates |
| JPS543043A (en) | 1977-06-10 | 1979-01-11 | Meiji Seika Kaisha Ltd | Amino-glycoside antibiotics; 1-n-(omega-aminoalkanesulfonyl)derivatives and their preparation |
| FR2427341A1 (fr) | 1978-06-02 | 1979-12-28 | Delalande Sa | Nouveaux derives aminoglycosidiques hemisynthetiques, leur procede de preparation et leur application en therapeutique |
| JPH0446189A (ja) | 1990-06-08 | 1992-02-17 | Meiji Seika Kaisha Ltd | 新規なリボスタマイシン誘導体 |
| EP2390255B1 (en) | 2006-04-03 | 2016-07-13 | Technion Research & Development Foundation Ltd. | Novel aminoglycosides and uses thereof in the treatment of genetic disorders |
| WO2011044538A1 (en) * | 2009-10-09 | 2011-04-14 | Achaogen, Inc. | Antibacterial aminoglycoside analogs |
| HRP20180056T1 (hr) | 2010-11-18 | 2018-02-09 | Technion Research & Development Foundation Ltd. | Aminoglikozidi i upotreba istih u svrhu liječenja genetskih poremećaja |
| CA2949754A1 (en) * | 2014-06-05 | 2015-12-10 | Eloxx Pharmaceuticals Ltd. | Use of aminoglycoside analogs in the treatment of rett syndrome |
| EP3344640A4 (en) | 2015-09-02 | 2019-05-01 | Eloxx Pharmaceuticals Ltd. | AMINO-LIKES DERIVATIVES AND USES THEREOF FOR THE TREATMENT OF GENETIC DISEASES |
| EP3350194A4 (en) | 2015-09-02 | 2019-04-24 | Eloxx Pharmaceuticals Ltd. | AMINO-LIKES DERIVATIVES AND USES THEREOF FOR THE TREATMENT OF GENETIC DISEASES |
| EP3344641A4 (en) | 2015-09-02 | 2019-09-18 | Eloxx Pharmaceuticals Ltd. | AMINO-LIKES DERIVATIVES AND USES THEREOF FOR THE TREATMENT OF GENETIC DISEASES |
-
2018
- 2018-03-15 AU AU2018235441A patent/AU2018235441C1/en active Active
- 2018-03-15 CA CA3055883A patent/CA3055883A1/en active Pending
- 2018-03-15 CN CN202311295323.3A patent/CN117466958A/zh active Pending
- 2018-03-15 JP JP2019551278A patent/JP7187471B2/ja active Active
- 2018-03-15 CN CN201880032661.9A patent/CN110637024B/zh not_active Expired - Fee Related
- 2018-03-15 EP EP18767330.6A patent/EP3609902A4/en not_active Withdrawn
- 2018-03-15 WO PCT/IL2018/050306 patent/WO2018167794A1/en not_active Ceased
- 2018-03-15 US US16/493,732 patent/US11136345B2/en active Active
- 2018-03-15 BR BR112019018834A patent/BR112019018834A2/pt not_active Application Discontinuation
-
2019
- 2019-09-15 IL IL269364A patent/IL269364B/en unknown
-
2021
- 2021-10-04 US US17/493,672 patent/US20220033428A1/en not_active Abandoned
-
2022
- 2022-10-18 AU AU2022256098A patent/AU2022256098C1/en active Active
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