ES2841324T3 - Proceso para la 6,7-alfa-epoxidación de 4,6-dienos esteroideos - Google Patents
Proceso para la 6,7-alfa-epoxidación de 4,6-dienos esteroideos Download PDFInfo
- Publication number
- ES2841324T3 ES2841324T3 ES17725742T ES17725742T ES2841324T3 ES 2841324 T3 ES2841324 T3 ES 2841324T3 ES 17725742 T ES17725742 T ES 17725742T ES 17725742 T ES17725742 T ES 17725742T ES 2841324 T3 ES2841324 T3 ES 2841324T3
- Authority
- ES
- Spain
- Prior art keywords
- general formula
- alkyl
- group
- halo
- compound
- 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.)
- Active
Links
- 0 C[C@](**)[C@@](C(*)CC1C(C(C2)[C@@]3(C)CC4)C=CC3=CC4=O)[C@@]1(C)C2*=C Chemical compound C[C@](**)[C@@](C(*)CC1C(C(C2)[C@@]3(C)CC4)C=CC3=CC4=O)[C@@]1(C)C2*=C 0.000 description 7
- RDEAHSQXFDTFBM-ZAEUZMPYSA-N C[C@@H](C(CC1)[C@@](C)(CCC2[C@@]3(C)CC4)C1C2C=CC3=CC4=O)/C=C/C(O)=O Chemical compound C[C@@H](C(CC1)[C@@](C)(CCC2[C@@]3(C)CC4)C1C2C=CC3=CC4=O)/C=C/C(O)=O RDEAHSQXFDTFBM-ZAEUZMPYSA-N 0.000 description 2
- MPXMCHHSSMKXMF-YWRKWLGMSA-N CCOC(/C=C/[C@@H](C)C(CC1)[C@@](C)(CCC2[C@@]3(C)CC4)C1C2C=CC3=CC4=O)=O Chemical compound CCOC(/C=C/[C@@H](C)C(CC1)[C@@](C)(CCC2[C@@]3(C)CC4)C1C2C=CC3=CC4=O)=O MPXMCHHSSMKXMF-YWRKWLGMSA-N 0.000 description 1
- OCZIOLLYUOEAQJ-GBKJTZMJSA-N CC[C@H]([C@H](CC(CC1)=O)[C@@]1(C)C(CC1)C2C(CC3)[C@@]1(C)[C@H]3[C@H](C)CCC(O)=O)C2=O Chemical compound CC[C@H]([C@H](CC(CC1)=O)[C@@]1(C)C(CC1)C2C(CC3)[C@@]1(C)[C@H]3[C@H](C)CCC(O)=O)C2=O OCZIOLLYUOEAQJ-GBKJTZMJSA-N 0.000 description 1
- NGELWCUNJHNRKU-UHMSGQPZSA-N C[C@@H](C(CC1)C(C)(CCC2[C@@]3(C)CC4)C1C2C=CC3=CC4=O)/C=C/C(NS(C1CC1)(=O)=O)=O Chemical compound C[C@@H](C(CC1)C(C)(CCC2[C@@]3(C)CC4)C1C2C=CC3=CC4=O)/C=C/C(NS(C1CC1)(=O)=O)=O NGELWCUNJHNRKU-UHMSGQPZSA-N 0.000 description 1
- NWQOGTWCZNSHHC-KYIYPNJCSA-N C[C@@H](C(CC1)[C@@](C)(CC2)C1C([C@@H]1O[C@@H]11)C2[C@@](C)(CC2)C1=CC2=O)/C=C/C(NS(c(cc1)ccc1OC(F)(F)F)(=O)=O)=O Chemical compound C[C@@H](C(CC1)[C@@](C)(CC2)C1C([C@@H]1O[C@@H]11)C2[C@@](C)(CC2)C1=CC2=O)/C=C/C(NS(c(cc1)ccc1OC(F)(F)F)(=O)=O)=O NWQOGTWCZNSHHC-KYIYPNJCSA-N 0.000 description 1
- BNJBNUKQHKMQRE-DEMIVQTHSA-N C[C@H](CC#N)C(CC1)[C@@](C)(CCC2[C@]3(C)CC4)C1C2C=CC3=CC4=O Chemical compound C[C@H](CC#N)C(CC1)[C@@](C)(CCC2[C@]3(C)CC4)C1C2C=CC3=CC4=O BNJBNUKQHKMQRE-DEMIVQTHSA-N 0.000 description 1
- BNJBNUKQHKMQRE-FVUFJZHCSA-N C[C@H](CC#N)[C@@H](CC1)[C@@](C)(CCC2[C@@]3(C)CC4)C1C2C=CC3=CC4=O Chemical compound C[C@H](CC#N)[C@@H](CC1)[C@@](C)(CCC2[C@@]3(C)CC4)C1C2C=CC3=CC4=O BNJBNUKQHKMQRE-FVUFJZHCSA-N 0.000 description 1
- OBWZWWLOOIRLFT-IRYAPPDHSA-N C[C@H](CC(C(OC)=O)C(OC)=O)C(CC1)[C@@](C)(CC2)C1C(CC1)C2[C@@](C)(CC2)C1=CC2=O Chemical compound C[C@H](CC(C(OC)=O)C(OC)=O)C(CC1)[C@@](C)(CC2)C1C(CC1)C2[C@@](C)(CC2)C1=CC2=O OBWZWWLOOIRLFT-IRYAPPDHSA-N 0.000 description 1
- XXAIOHKWBTUQKJ-PBKWIEQUSA-N C[C@H](CCC#N)C(CC1)[C@@](C)(CC2)C1C(CC1)C2C(C)(CC2)C1=CC2=O Chemical compound C[C@H](CCC#N)C(CC1)[C@@](C)(CC2)C1C(CC1)C2C(C)(CC2)C1=CC2=O XXAIOHKWBTUQKJ-PBKWIEQUSA-N 0.000 description 1
- TVLAZDVLUCRKPL-PBKWIEQUSA-N C[C@H](CCC#N)C1C=CC(C2C=C3)[C@]1(C)CCC2C(C)(CC1)C3=CC1=O Chemical compound C[C@H](CCC#N)C1C=CC(C2C=C3)[C@]1(C)CCC2C(C)(CC1)C3=CC1=O TVLAZDVLUCRKPL-PBKWIEQUSA-N 0.000 description 1
- ZNWOYQVXPIEQRC-IESYDMTLSA-N C[C@H](CO)[C@@H](CC1)[C@@](C)(CC2)C1C(CC1)C2[C@@](C)(CC2)C1=CC2=O Chemical compound C[C@H](CO)[C@@H](CC1)[C@@](C)(CC2)C1C(CC1)C2[C@@](C)(CC2)C1=CC2=O ZNWOYQVXPIEQRC-IESYDMTLSA-N 0.000 description 1
- NJPNLOUORSQRLE-JBLPTAOASA-N C[C@H](COS(C)(=O)=O)C(CC1)[C@@](C)(CC2)C1C([C@@H]1O[C@@H]11)C2[C@@](C)(CC2)C1=CC2=O Chemical compound C[C@H](COS(C)(=O)=O)C(CC1)[C@@](C)(CC2)C1C([C@@H]1O[C@@H]11)C2[C@@](C)(CC2)C1=CC2=O NJPNLOUORSQRLE-JBLPTAOASA-N 0.000 description 1
- JFGNAYZCSHYUJF-GANSKVLZSA-N C[C@](CC1)(C(CC2)C(CC3)C1[C@@](C)(CC1)C3=CC1=O)/C2=C\C Chemical compound C[C@](CC1)(C(CC2)C(CC3)C1[C@@](C)(CC1)C3=CC1=O)/C2=C\C JFGNAYZCSHYUJF-GANSKVLZSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
- C07J41/0088—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 containing unsubstituted amino radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
- C07J71/0005—Oxygen-containing hetero ring
- C07J71/001—Oxiranes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
- C07J9/005—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane containing a carboxylic function directly attached or attached by a chain containing only carbon atoms to the cyclopenta[a]hydrophenanthrene skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J13/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having a carbon-to-carbon double bond from or to position 17
- C07J13/007—Normal steroids containing carbon, hydrogen, halogen or oxygen having a carbon-to-carbon double bond from or to position 17 with double bond in position 17 (20)
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J17/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, having an oxygen-containing hetero ring not condensed with the cyclopenta(a)hydrophenanthrene skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J31/00—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring
- C07J31/006—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring not covered by C07J31/003
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
- C07J41/0055—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 the 17-beta position being substituted by an uninterrupted chain of at least three carbon atoms which may or may not be branched, e.g. cholane or cholestane derivatives, optionally cyclised, e.g. 17-beta-phenyl or 17-beta-furyl derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
- C07J41/0055—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 the 17-beta position being substituted by an uninterrupted chain of at least three carbon atoms which may or may not be branched, e.g. cholane or cholestane derivatives, optionally cyclised, e.g. 17-beta-phenyl or 17-beta-furyl derivatives
- C07J41/0061—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 the 17-beta position being substituted by an uninterrupted chain of at least three carbon atoms which may or may not be branched, e.g. cholane or cholestane derivatives, optionally cyclised, e.g. 17-beta-phenyl or 17-beta-furyl derivatives one of the carbon atoms being part of an amide group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
- C07J41/0094—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 containing nitrile radicals, including thiocyanide radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J43/00—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J43/003—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton not condensed
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J51/00—Normal steroids with unmodified cyclopenta(a)hydrophenanthrene skeleton not provided for in groups C07J1/00 - C07J43/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Toxicology (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB1608776.9A GB201608776D0 (en) | 2016-05-18 | 2016-05-18 | Methods and compounds |
| 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 (1)
| Publication Number | Publication Date |
|---|---|
| ES2841324T3 true ES2841324T3 (es) | 2021-07-08 |
Family
ID=56320628
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES17725742T Active ES2841324T3 (es) | 2016-05-18 | 2017-05-18 | Proceso para la 6,7-alfa-epoxidación de 4,6-dienos esteroideos |
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 (7)
| 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 |
| CN114957371B (zh) * | 2021-09-08 | 2023-10-31 | 湖南醇康医药科技有限公司 | 地屈孕酮及其中间体化合物的制备方法 |
| GB202416085D0 (en) | 2024-10-31 | 2024-12-18 | Nzp Uk Ltd | Reduction process |
Family Cites Families (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| ATE156158T1 (de) | 1992-04-14 | 1997-08-15 | Cornell Res Foundation Inc | Makromoleküle auf basis von dendritischen polymeren und verfahren zur herstellung |
| US5643575A (en) | 1993-10-27 | 1997-07-01 | Enzon, Inc. | Non-antigenic branched polymer conjugates |
| US5932462A (en) | 1995-01-10 | 1999-08-03 | Shearwater Polymers, Inc. | Multiarmed, monofunctional, polymer for coupling to molecules and surfaces |
| US5723636A (en) | 1996-04-12 | 1998-03-03 | National Starch And Chemical Investment Holding Corporation | Methyltrioxorhenium-urea hydrogen peroxide epoxidation of olefins |
| DK1392714T3 (da) | 2001-03-12 | 2006-01-09 | Intercept Pharmaceuticals Inc | Steroider som agonister for FXR |
| US20090062256A1 (en) | 2001-06-01 | 2009-03-05 | Bristol-Myers Squibb Pharma Company | LACTAMS SUBSTITUTED BY CYCLIC SUCCINATES AS INHIBITORS OF Abeta PROTEIN PRODUCTION |
| EP1446438A2 (en) | 2001-11-07 | 2004-08-18 | Nektar Therapeutics Al, Corporation | Branched polymers and their conjugates |
| ITMI20030352A1 (it) | 2003-02-27 | 2004-08-28 | Chemi Spa | Metodo per la sintesi di metiltriossorenio. |
| EP1568706A1 (en) | 2004-02-26 | 2005-08-31 | Intercept Pharmaceuticals, Inc. | Novel steroid agonist for FXR |
| EP1775304A4 (en) | 2004-07-13 | 2010-04-28 | Mitsubishi Chem Corp | PROCESS FOR THE PRODUCTION OF STEROIDS |
| ITMI20050912A1 (it) * | 2005-05-19 | 2006-11-20 | Erregierre Spa | Processo di preparazione di acidi 3-a-ya(b)-diidrossi-6-a(b)-alchil-5b-colanici |
| JP2007210888A (ja) * | 2006-01-12 | 2007-08-23 | Mitsubishi Chemicals Corp | ステロイド化合物の製造方法 |
| DK2040713T3 (da) | 2006-06-27 | 2014-09-29 | Intercept Pharmaceuticals Inc | Galdesyrederivater som fxr-ligander til forebyggelsen eller behandlingen af fxr-medierede sygdomme eller tilstande |
| US8796249B2 (en) | 2008-07-30 | 2014-08-05 | Intercept Pharmaceuticals, Inc. | TGR5 modulators and methods of use thereof |
| AU2009316484B2 (en) | 2008-11-19 | 2015-04-16 | Intercept Pharmaceuticals, Inc. | TGR5 modulators and methods of use thereof |
| JP2013500986A (ja) | 2009-07-29 | 2013-01-10 | ザ・ユニバーシティ・オブ・シカゴ | 肝臓ｘ受容体アゴニスト |
| ES2822375T3 (es) | 2012-06-19 | 2021-04-30 | Intercept Pharmaceuticals Inc | Preparación de la forma no cristalina del ácido obeticólico |
| NZ707389A (en) | 2012-10-26 | 2018-08-31 | Intercept Pharmaceuticals Inc | Process for preparing bile acid derivatives |
| WO2014085474A1 (en) | 2012-11-28 | 2014-06-05 | Intercept Pharmaceuticals, Inc. | Treatment of pulmonary disease |
| US20140206657A1 (en) | 2013-01-18 | 2014-07-24 | City Of Hope | Bile acid analog tgr5 agonists |
| WO2015183794A1 (en) | 2014-05-27 | 2015-12-03 | City Of Hope | Tgr5 agonist complexes for treating diabetes and cancer |
| KR102526632B1 (ko) | 2014-11-19 | 2023-04-27 | 엔제트피 유케이 리미티드 | 스테로이드 FXR 조절인자를 제조하기 위한 중간체로서의 5β-6-알킬-7-하이드록시-3-온 스테로이드 |
| EA033427B1 (ru) * | 2014-11-19 | 2019-10-31 | Nzp Uk Ltd | 6-алкил-7-гидрокси-4-ен-3-оновые стероиды в качестве промежуточных соединений для получения стероидных модуляторов fxr |
| JP6698085B2 (ja) | 2014-11-19 | 2020-05-27 | エヌゼットピー ユーケー リミテッド | ステロイドＦＸＲモジュレーター製造のための中間体としての６α−アルキル−６，７−ジオン−ステロイド |
| ES2748692T3 (es) | 2014-11-19 | 2020-03-17 | Nzp Uk Ltd | Esteroides 6.alfa.-alquil-3,7-diona como intermedios para la producción de moduladores FXR de esteroides |
| WO2016086115A1 (en) | 2014-11-26 | 2016-06-02 | 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 |
| GB201608777D0 (en) * | 2016-05-18 | 2016-06-29 | Dextra Lab Ltd | Compounds |
| GB201608779D0 (en) * | 2016-05-18 | 2016-06-29 | Dextra Lab Ltd | Methods and compounds |
-
2016
- 2016-05-18 GB GBGB1608776.9A patent/GB201608776D0/en not_active Ceased
-
2017
- 2017-05-18 AU AU2017265445A patent/AU2017265445B2/en active Active
- 2017-05-18 PT PT177257425T patent/PT3458467T/pt unknown
- 2017-05-18 ES ES17725742T patent/ES2841324T3/es 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 EP EP17725742.5A patent/EP3458467B1/en active Active
- 2017-05-18 EA EA201892516A patent/EA038224B1/ru unknown
- 2017-05-18 KR KR1020187035835A patent/KR102489565B1/ko active Active
- 2017-05-18 CA CA3024283A patent/CA3024283C/en active Active
- 2017-05-18 JP JP2018560672A patent/JP7034094B2/ja active Active
- 2017-05-18 CN CN201780030784.4A patent/CN109415404B/zh active Active
- 2017-05-18 MX MX2018014130A patent/MX378594B/es unknown
- 2017-05-18 DK DK17725742.5T patent/DK3458467T3/da active
Also Published As
| Publication number | Publication date |
|---|---|
| US10766921B2 (en) | 2020-09-08 |
| EA038224B1 (ru) | 2021-07-27 |
| KR20190007011A (ko) | 2019-01-21 |
| JP7034094B2 (ja) | 2022-03-11 |
| DK3458467T3 (da) | 2020-12-14 |
| AU2017265445B2 (en) | 2020-12-03 |
| KR102489565B1 (ko) | 2023-01-17 |
| CN109415404A (zh) | 2019-03-01 |
| CN109415404B (zh) | 2022-08-26 |
| EP3458467B1 (en) | 2020-09-30 |
| US20190309012A1 (en) | 2019-10-10 |
| PT3458467T (pt) | 2021-01-05 |
| GB201608776D0 (en) | 2016-06-29 |
| EP3458467A1 (en) | 2019-03-27 |
| MX2018014130A (es) | 2019-04-29 |
| CA3024283C (en) | 2024-07-02 |
| WO2017199036A1 (en) | 2017-11-23 |
| AU2017265445A1 (en) | 2018-11-15 |
| EA201892516A1 (ru) | 2019-05-31 |
| BR112018073492A2 (pt) | 2019-03-26 |
| JP2019516729A (ja) | 2019-06-20 |
| CA3024283A1 (en) | 2017-11-23 |
| MX378594B (es) | 2025-03-11 |
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