JP2019516729A5 - - Google Patents
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- JP2019516729A5 JP2019516729A5 JP2018560672A JP2018560672A JP2019516729A5 JP 2019516729 A5 JP2019516729 A5 JP 2019516729A5 JP 2018560672 A JP2018560672 A JP 2018560672A JP 2018560672 A JP2018560672 A JP 2018560672A JP 2019516729 A5 JP2019516729 A5 JP 2019516729A5
- Authority
- JP
- Japan
- Prior art keywords
- compound
- general formula
- alkyl
- halo
- optionally substituted
- 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
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- 150000001875 compounds Chemical class 0.000 claims description 112
- 125000000217 alkyl group Chemical group 0.000 claims description 69
- 238000000034 method Methods 0.000 claims description 62
- 125000001475 halogen functional group Chemical group 0.000 claims description 55
- 125000001424 substituent group Chemical group 0.000 claims description 40
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 34
- 229910052799 carbon Inorganic materials 0.000 claims description 28
- 125000006708 (C5-C14) heteroaryl group Chemical group 0.000 claims description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims description 25
- 125000005915 C6-C14 aryl group Chemical group 0.000 claims description 23
- 125000000623 heterocyclic group Chemical group 0.000 claims description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
- -1 C(O)Ph Chemical group 0.000 claims description 14
- 239000007800 oxidant agent Substances 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 13
- 239000002904 solvent Substances 0.000 claims description 12
- 230000000155 isotopic effect Effects 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- 125000002947 alkylene group Chemical group 0.000 claims description 9
- 125000004429 atom Chemical group 0.000 claims description 9
- VZSXFJPZOCRDPW-UHFFFAOYSA-N carbanide;trioxorhenium Chemical compound [CH3-].O=[Re](=O)=O VZSXFJPZOCRDPW-UHFFFAOYSA-N 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 125000005647 linker group Chemical group 0.000 claims description 9
- 125000006649 (C2-C20) alkynyl group Chemical group 0.000 claims description 8
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 125000004494 ethyl ester group Chemical group 0.000 claims description 8
- 150000003536 tetrazoles Chemical class 0.000 claims description 8
- BYEAHWXPCBROCE-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound FC(F)(F)C(O)C(F)(F)F BYEAHWXPCBROCE-UHFFFAOYSA-N 0.000 claims description 7
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical group OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 7
- 239000002202 Polyethylene glycol Substances 0.000 claims description 7
- 239000003054 catalyst Substances 0.000 claims description 7
- 125000003827 glycol group Chemical group 0.000 claims description 7
- 239000003446 ligand Substances 0.000 claims description 7
- 230000003647 oxidation Effects 0.000 claims description 7
- 238000007254 oxidation reaction Methods 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 229920001223 polyethylene glycol Polymers 0.000 claims description 7
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 6
- 125000004450 alkenylene group Chemical group 0.000 claims description 6
- 150000001540 azides Chemical class 0.000 claims description 6
- 239000003638 chemical reducing agent Substances 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 125000006239 protecting group Chemical group 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 239000007810 chemical reaction solvent Substances 0.000 claims description 5
- 230000001590 oxidative effect Effects 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 4
- GETTZEONDQJALK-UHFFFAOYSA-N (trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 claims description 4
- ITQTTZVARXURQS-UHFFFAOYSA-N 3-methylpyridine Chemical compound CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 claims description 4
- RHQDFWAXVIIEBN-UHFFFAOYSA-N Trifluoroethanol Chemical compound OCC(F)(F)F RHQDFWAXVIIEBN-UHFFFAOYSA-N 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000004419 alkynylene group Chemical group 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- ULDHMXUKGWMISQ-UHFFFAOYSA-N carvone Chemical compound CC(=C)C1CC=C(C)C(=O)C1 ULDHMXUKGWMISQ-UHFFFAOYSA-N 0.000 claims description 4
- 235000019439 ethyl acetate Nutrition 0.000 claims description 4
- ZQBFAOFFOQMSGJ-UHFFFAOYSA-N hexafluorobenzene Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1F ZQBFAOFFOQMSGJ-UHFFFAOYSA-N 0.000 claims description 4
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 claims description 4
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims description 4
- XKVUYEYANWFIJX-UHFFFAOYSA-N 5-methyl-1h-pyrazole Chemical compound CC1=CC=NN1 XKVUYEYANWFIJX-UHFFFAOYSA-N 0.000 claims description 3
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 3
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 3
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 3
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 3
- 230000002152 alkylating effect Effects 0.000 claims description 3
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 3
- 239000003153 chemical reaction reagent Substances 0.000 claims description 3
- 125000002524 organometallic group Chemical group 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- YIHRGKXNJGKSOT-UHFFFAOYSA-N 1,1,2,2,3,3-hexafluorobutan-1-ol Chemical compound CC(F)(F)C(F)(F)C(O)(F)F YIHRGKXNJGKSOT-UHFFFAOYSA-N 0.000 claims description 2
- GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical compound N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 claims description 2
- 239000005973 Carvone Substances 0.000 claims description 2
- 239000002879 Lewis base Substances 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
- VTIIJXUACCWYHX-UHFFFAOYSA-L disodium;carboxylatooxy carbonate Chemical compound [Na+].[Na+].[O-]C(=O)OOC([O-])=O VTIIJXUACCWYHX-UHFFFAOYSA-L 0.000 claims description 2
- 150000007527 lewis bases Chemical class 0.000 claims description 2
- 125000005544 phthalimido group Chemical group 0.000 claims description 2
- GPHQHTOMRSGBNZ-UHFFFAOYSA-N pyridine-4-carbonitrile Chemical compound N#CC1=CC=NC=C1 GPHQHTOMRSGBNZ-UHFFFAOYSA-N 0.000 claims description 2
- 229940045872 sodium percarbonate Drugs 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000000126 substance Substances 0.000 description 18
- 0 C[C@](**)[C@](C(*)C[C@](C1)C2[C@@]3O[C@@]33)[C@@]1C(*)CC2[C@@](C)(CC1)C3=CC1=O Chemical compound C[C@](**)[C@](C(*)C[C@](C1)C2[C@@]3O[C@@]33)[C@@]1C(*)CC2[C@@](C)(CC1)C3=CC1=O 0.000 description 15
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 4
- QOITVJFGQSYVEC-QUVUXFPMSA-N (8S,9S,10R,13S,14S,17R)-10,13-dimethyl-17-[(2S)-1-[5-(4-methylphenyl)sulfonyltetrazol-1-yl]propan-2-yl]-1,2,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-one Chemical compound S(=O)(=O)(C1=CC=C(C)C=C1)C1=NN=NN1C[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C=CC4=CC(CC[C@]4(C)[C@H]3CC[C@]12C)=O QOITVJFGQSYVEC-QUVUXFPMSA-N 0.000 description 3
- VGABOYDXXXLGND-HOFZUOGSSA-N (2S)-2-[(8S,9S,10R,13S,14S,17R)-10,13-dimethyl-3-oxo-1,2,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]propanal Chemical compound C(=O)[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C=CC4=CC(CC[C@]4(C)[C@H]3CC[C@]12C)=O VGABOYDXXXLGND-HOFZUOGSSA-N 0.000 description 2
- BNJBNUKQHKMQRE-SEXBJWDNSA-N (3R)-3-[(8S,9S,10R,13R,14S,17R)-10,13-dimethyl-3-oxo-1,2,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]butanenitrile Chemical compound C(#N)C[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C=CC4=CC(CC[C@]4(C)[C@H]3CC[C@]12C)=O BNJBNUKQHKMQRE-SEXBJWDNSA-N 0.000 description 2
- ZQQPNEANPAYUGN-HOFZUOGSSA-N (8S,9S,10R,13S,14S,17R)-17-[(2S)-1-aminopropan-2-yl]-10,13-dimethyl-1,2,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-one Chemical compound NC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C=CC4=CC(CC[C@]4(C)[C@H]3CC[C@]12C)=O ZQQPNEANPAYUGN-HOFZUOGSSA-N 0.000 description 2
- DVGPACHJMSFAIS-HOFZUOGSSA-N (8S,9S,10R,13S,14S,17R)-17-[(2S)-1-bromopropan-2-yl]-10,13-dimethyl-1,2,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-one Chemical compound BrC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C=CC4=CC(CC[C@]4(C)[C@H]3CC[C@]12C)=O DVGPACHJMSFAIS-HOFZUOGSSA-N 0.000 description 2
- RVMKHXACNVHOJU-XMLICAENSA-N (8S,9S,10R,13S,14S,17R)-17-[(3S)-1-dimethylsilyloxy-4,4-dimethylpentan-3-yl]-10,13-dimethyl-1,2,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-one Chemical compound C(C)(C)(C)[C@@H](CCO[SiH](C)C)[C@H]1CC[C@H]2[C@@H]3C=CC4=CC(CC[C@]4(C)[C@H]3CC[C@]12C)=O RVMKHXACNVHOJU-XMLICAENSA-N 0.000 description 2
- WJKJZKIHLUIQTO-HOFZUOGSSA-N (8s,9s,10r,13s,14s,17r)-17-[(2s)-1-hydroxypropan-2-yl]-10,13-dimethyl-1,2,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-one Chemical compound C1=CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@@H](CO)C)[C@@]1(C)CC2 WJKJZKIHLUIQTO-HOFZUOGSSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- NTXWUXDNKRIRJL-QMIPSKNFSA-N [(2S)-2-[(8S,9S,10R,13S,14S,17R)-10,13-dimethyl-3-oxo-1,2,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]propyl] acetate Chemical compound C(C)(=O)OC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C=CC4=CC(CC[C@]4(C)[C@H]3CC[C@]12C)=O NTXWUXDNKRIRJL-QMIPSKNFSA-N 0.000 description 2
- JCKVHVKNWAWEKH-SEXBJWDNSA-N [(2S)-2-[(8S,9S,10R,13S,14S,17R)-10,13-dimethyl-3-oxo-1,2,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]propyl] methanesulfonate Chemical compound S(=O)(=O)(C)OC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C=CC4=CC(CC[C@]4(C)[C@H]3CC[C@]12C)=O JCKVHVKNWAWEKH-SEXBJWDNSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- WMSPXQIQBQAWLL-UHFFFAOYSA-N cyclopropanesulfonamide Chemical compound NS(=O)(=O)C1CC1 WMSPXQIQBQAWLL-UHFFFAOYSA-N 0.000 description 2
- 238000006735 epoxidation reaction Methods 0.000 description 2
- 125000001072 heteroaryl group Chemical group 0.000 description 2
- 229910052702 rhenium Inorganic materials 0.000 description 2
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical group [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 2
- ITYISIPEDFCRRC-PKEFDYQUSA-N C[C@H](C[n]1nnnc1C)C(CCC(C1)C2[C@@H]3O[C@@H]33)C1CCC2[C@@](C)(CC1)C3=CC1=O Chemical compound C[C@H](C[n]1nnnc1C)C(CCC(C1)C2[C@@H]3O[C@@H]33)C1CCC2[C@@](C)(CC1)C3=CC1=O ITYISIPEDFCRRC-PKEFDYQUSA-N 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- AQLJVWUFPCUVLO-UHFFFAOYSA-N urea hydrogen peroxide Chemical compound OO.NC(N)=O AQLJVWUFPCUVLO-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB1608776.9A GB201608776D0 (en) | 2016-05-18 | 2016-05-18 | Methods and compounds |
| GB1608776.9 | 2016-05-18 | ||
| PCT/GB2017/051389 WO2017199036A1 (en) | 2016-05-18 | 2017-05-18 | Process and intermediates for the 6,7-alpha-epoxidation of steroid 4,6-dienes |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2019516729A JP2019516729A (ja) | 2019-06-20 |
| JP2019516729A5 true JP2019516729A5 (enExample) | 2020-07-02 |
| JP7034094B2 JP7034094B2 (ja) | 2022-03-11 |
Family
ID=56320628
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018560672A Active JP7034094B2 (ja) | 2016-05-18 | 2017-05-18 | ステロイド４，６－ジエンの６，７－α－エポキシ化のための方法及び中間体 |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US10766921B2 (enExample) |
| EP (1) | EP3458467B1 (enExample) |
| JP (1) | JP7034094B2 (enExample) |
| KR (1) | KR102489565B1 (enExample) |
| CN (1) | CN109415404B (enExample) |
| AU (1) | AU2017265445B2 (enExample) |
| CA (1) | CA3024283C (enExample) |
| DK (1) | DK3458467T3 (enExample) |
| EA (1) | EA038224B1 (enExample) |
| ES (1) | ES2841324T3 (enExample) |
| GB (1) | GB201608776D0 (enExample) |
| MX (1) | MX378594B (enExample) |
| PT (1) | PT3458467T (enExample) |
| WO (1) | WO2017199036A1 (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB201608776D0 (en) | 2016-05-18 | 2016-06-29 | Dextra Lab Ltd | Methods and compounds |
| GB201608777D0 (en) | 2016-05-18 | 2016-06-29 | Dextra Lab Ltd | Compounds |
| GB201812382D0 (en) | 2018-07-30 | 2018-09-12 | Nzp Uk Ltd | Compounds |
| CN111560045A (zh) * | 2020-06-23 | 2020-08-21 | 江苏佳尔科药业集团股份有限公司 | 一种以ba为原料合成石胆酸的方法 |
| CN114957372B (zh) * | 2021-12-07 | 2023-10-31 | 湖南醇康医药科技有限公司 | 10α-甲基-5,7-二烯甾体化合物和地屈孕酮的制备方法 |
| CN114957368B (zh) * | 2021-09-08 | 2024-07-26 | 湖南科益新生物医药有限公司 | 中间体化合物及其制备方法和应用 |
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| US2624748A (en) | 1950-09-09 | 1953-01-06 | Upjohn Co | Bisnorchola-4, 6-dien-3-one-22-al |
| IT1088094B (it) | 1976-10-14 | 1985-06-04 | Hoffmann La Roche | Derivati del pregnano |
| US4289872A (en) | 1979-04-06 | 1981-09-15 | Allied Corporation | Macromolecular highly branched homogeneous compound based on lysine units |
| US5229490A (en) | 1987-05-06 | 1993-07-20 | The Rockefeller University | Multiple antigen peptide system |
| DE3902357A1 (de) | 1989-01-27 | 1990-08-02 | Hoechst Ag | Verwendung von rheniumorganischen verbindungen zur oxidation von c-c-mehrfachbindungen, darauf basierende oxidationsverfahren und neue rheniumorganische verbindungen |
| US5166372A (en) | 1992-02-07 | 1992-11-24 | Arco Chemical Technology, L.P. | Epoxidation process |
| JPH07505915A (ja) | 1992-04-14 | 1995-06-29 | コーネル リサーチ ファウンデーション、インコーポレーテッド | 樹枝状巨大分子およびその製造法 |
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| CN107108688B (zh) | 2014-11-19 | 2019-10-29 | Nzp英国有限公司 | 作为制备类固醇FXR调节剂的中间体的6α-烷基-3,7-二酮类固醇 |
| US11578097B2 (en) | 2014-11-26 | 2023-02-14 | Enanta Pharmaceuticals, Inc. | Tetrazole derivatives of bile acids as FXR/TGR5 agonists and methods of use thereof |
| CN105348365A (zh) | 2014-12-03 | 2016-02-24 | 四川百利药业有限责任公司 | 一种胆酸衍生物及其制备方法、药物组合物和用途 |
| GB201608776D0 (en) | 2016-05-18 | 2016-06-29 | Dextra Lab Ltd | Methods and compounds |
| GB201608779D0 (en) * | 2016-05-18 | 2016-06-29 | Dextra Lab Ltd | Methods and compounds |
| GB201608777D0 (en) | 2016-05-18 | 2016-06-29 | Dextra Lab Ltd | Compounds |
-
2016
- 2016-05-18 GB GBGB1608776.9A patent/GB201608776D0/en not_active Ceased
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2017
- 2017-05-18 DK DK17725742.5T patent/DK3458467T3/da active
- 2017-05-18 EA EA201892516A patent/EA038224B1/ru unknown
- 2017-05-18 CN CN201780030784.4A patent/CN109415404B/zh active Active
- 2017-05-18 CA CA3024283A patent/CA3024283C/en active Active
- 2017-05-18 AU AU2017265445A patent/AU2017265445B2/en active Active
- 2017-05-18 US US16/302,057 patent/US10766921B2/en active Active
- 2017-05-18 WO PCT/GB2017/051389 patent/WO2017199036A1/en not_active Ceased
- 2017-05-18 JP JP2018560672A patent/JP7034094B2/ja active Active
- 2017-05-18 KR KR1020187035835A patent/KR102489565B1/ko active Active
- 2017-05-18 ES ES17725742T patent/ES2841324T3/es active Active
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