JP2020515636A5 - - Google Patents
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- JP2020515636A5 JP2020515636A5 JP2020501850A JP2020501850A JP2020515636A5 JP 2020515636 A5 JP2020515636 A5 JP 2020515636A5 JP 2020501850 A JP2020501850 A JP 2020501850A JP 2020501850 A JP2020501850 A JP 2020501850A JP 2020515636 A5 JP2020515636 A5 JP 2020515636A5
- Authority
- JP
- Japan
- Prior art keywords
- optionally substituted
- compound according
- alkyl
- halo
- cycloalkyl
- 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 109
- 125000005843 halogen group Chemical group 0.000 claims description 53
- 125000003118 aryl group Chemical group 0.000 claims description 32
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 28
- 125000001424 substituent group Chemical group 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 22
- 125000001072 heteroaryl group Chemical group 0.000 claims description 20
- -1 R 21 Chemical compound 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 18
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 15
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 12
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 12
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 12
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 12
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 12
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 12
- 208000031226 Hyperlipidaemia Diseases 0.000 claims description 12
- 125000004414 alkyl thio group Chemical group 0.000 claims description 12
- 125000000304 alkynyl group Chemical group 0.000 claims description 12
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 12
- 229910052805 deuterium Inorganic materials 0.000 claims description 12
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 12
- 125000001188 haloalkyl group Chemical group 0.000 claims description 12
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 12
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 12
- 150000002431 hydrogen Chemical class 0.000 claims description 12
- 208000017169 kidney disease Diseases 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- 239000000651 prodrug Substances 0.000 claims description 12
- 229940002612 prodrug Drugs 0.000 claims description 12
- 125000003107 substituted aryl group Chemical group 0.000 claims description 12
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 12
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 10
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 claims description 10
- 208000032928 Dyslipidaemia Diseases 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 208000017170 Lipid metabolism disease Diseases 0.000 claims description 10
- 125000001153 fluoro group Chemical group F* 0.000 claims description 10
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
- 102100040134 Free fatty acid receptor 4 Human genes 0.000 claims description 8
- 101000890672 Homo sapiens Free fatty acid receptor 4 Proteins 0.000 claims description 8
- 201000010099 disease Diseases 0.000 claims description 8
- 230000000694 effects Effects 0.000 claims description 8
- 201000001421 hyperglycemia Diseases 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 6
- 201000001320 Atherosclerosis Diseases 0.000 claims description 6
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 6
- 208000032131 Diabetic Neuropathies Diseases 0.000 claims description 6
- SXGAGTVDWKQYCX-BQBZGAKWSA-N Glu-Met Chemical group CSCC[C@@H](C(O)=O)NC(=O)[C@@H](N)CCC(O)=O SXGAGTVDWKQYCX-BQBZGAKWSA-N 0.000 claims description 6
- 208000035150 Hypercholesterolemia Diseases 0.000 claims description 6
- 206010060378 Hyperinsulinaemia Diseases 0.000 claims description 6
- 206010020772 Hypertension Diseases 0.000 claims description 6
- 206010022489 Insulin Resistance Diseases 0.000 claims description 6
- 206010023379 Ketoacidosis Diseases 0.000 claims description 6
- 208000007976 Ketosis Diseases 0.000 claims description 6
- 208000001145 Metabolic Syndrome Diseases 0.000 claims description 6
- 150000001204 N-oxides Chemical class 0.000 claims description 6
- 208000008589 Obesity Diseases 0.000 claims description 6
- 206010030113 Oedema Diseases 0.000 claims description 6
- 201000001880 Sexual dysfunction Diseases 0.000 claims description 6
- 208000007536 Thrombosis Diseases 0.000 claims description 6
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 230000003451 hyperinsulinaemic effect Effects 0.000 claims description 6
- 201000008980 hyperinsulinism Diseases 0.000 claims description 6
- 208000020346 hyperlipoproteinemia Diseases 0.000 claims description 6
- 208000008338 non-alcoholic fatty liver disease Diseases 0.000 claims description 6
- 206010053219 non-alcoholic steatohepatitis Diseases 0.000 claims description 6
- 235000020824 obesity Nutrition 0.000 claims description 6
- 231100000872 sexual dysfunction Toxicity 0.000 claims description 6
- 239000012453 solvate Substances 0.000 claims description 6
- 208000011580 syndromic disease Diseases 0.000 claims description 6
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 6
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 4
- 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims description 4
- ISGHWXGVOSSTFA-UHFFFAOYSA-N 3-[3-(5-cyclobutyloxy-2-fluorophenyl)-1,2,4,5-tetrahydro-3-benzazepin-7-yl]propanoic acid Chemical compound C1(CCC1)OC=1C=CC(=C(C=1)N1CCC2=C(CC1)C=C(C=C2)CCC(=O)O)F ISGHWXGVOSSTFA-UHFFFAOYSA-N 0.000 claims description 4
- 208000013016 Hypoglycemia Diseases 0.000 claims description 4
- 206010028980 Neoplasm Diseases 0.000 claims description 4
- 208000017442 Retinal disease Diseases 0.000 claims description 4
- 206010038923 Retinopathy Diseases 0.000 claims description 4
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims description 4
- 239000008280 blood Substances 0.000 claims description 4
- 210000004369 blood Anatomy 0.000 claims description 4
- 201000011510 cancer Diseases 0.000 claims description 4
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
- 206010012601 diabetes mellitus Diseases 0.000 claims description 4
- 230000002218 hypoglycaemic effect Effects 0.000 claims description 4
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 claims description 4
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 208000017520 skin disease Diseases 0.000 claims description 4
- UMZRKIDNPFYNDC-CYBMUJFWSA-N (2R)-3-[3-[2-fluoro-5-(trifluoromethoxy)phenyl]-1,2,4,5-tetrahydro-3-benzazepin-7-yl]-2-methylpropanoic acid Chemical compound FC1=C(C=C(C=C1)OC(F)(F)F)N1CCC2=C(CC1)C=C(C=C2)C[C@H](C(=O)O)C UMZRKIDNPFYNDC-CYBMUJFWSA-N 0.000 claims description 2
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 2
- ZRHSQSMMKPJRMA-UHFFFAOYSA-N 2-[3-[2-fluoro-5-(trifluoromethoxy)phenyl]-1,2,4,5-tetrahydro-3-benzazepin-7-yl]cyclopropane-1-carboxylic acid Chemical compound FC1=C(C=C(C=C1)OC(F)(F)F)N1CCC2=C(CC1)C=C(C=C2)C1C(C1)C(=O)O ZRHSQSMMKPJRMA-UHFFFAOYSA-N 0.000 claims description 2
- FEOPYNYXOFGLIC-UHFFFAOYSA-N 3-[3-(2-fluoro-5-phenoxyphenyl)-1,2,4,5-tetrahydro-3-benzazepin-7-yl]propanoic acid Chemical compound FC1=C(C=C(C=C1)OC1=CC=CC=C1)N1CCC2=C(CC1)C=C(C=C2)CCC(=O)O FEOPYNYXOFGLIC-UHFFFAOYSA-N 0.000 claims description 2
- UKVIUUAPRXAWCA-UHFFFAOYSA-N 3-[3-(2-fluoro-5-propan-2-yloxyphenyl)-1,2,4,5-tetrahydro-3-benzazepin-7-yl]propanoic acid Chemical compound FC1=C(C=C(C=C1)OC(C)C)N1CCC2=C(CC1)C=C(C=C2)CCC(=O)O UKVIUUAPRXAWCA-UHFFFAOYSA-N 0.000 claims description 2
- NVRPMXRUDCRJHD-UHFFFAOYSA-N 3-[3-(3-fluoro-5-propan-2-yloxyphenyl)-1,2,4,5-tetrahydro-3-benzazepin-7-yl]propanoic acid Chemical compound FC=1C=C(C=C(C=1)OC(C)C)N1CCC2=C(CC1)C=C(C=C2)CCC(=O)O NVRPMXRUDCRJHD-UHFFFAOYSA-N 0.000 claims description 2
- DZEKRNYFTSYHOS-UHFFFAOYSA-N 3-[3-(5-cyclopropyloxy-2-fluorophenyl)-1,2,4,5-tetrahydro-3-benzazepin-7-yl]propanoic acid Chemical compound C1(CC1)OC=1C=CC(=C(C=1)N1CCC2=C(CC1)C=C(C=C2)CCC(=O)O)F DZEKRNYFTSYHOS-UHFFFAOYSA-N 0.000 claims description 2
- BYAXEYKIYWWMLA-UHFFFAOYSA-N 3-[3-[2-fluoro-5-(trifluoromethoxy)phenyl]-1,2,4,5-tetrahydro-3-benzazepin-7-yl]propanoic acid Chemical compound FC1=C(C=C(C=C1)OC(F)(F)F)N1CCC2=C(CC1)C=C(C=C2)CCC(=O)O BYAXEYKIYWWMLA-UHFFFAOYSA-N 0.000 claims description 2
- 206010012689 Diabetic retinopathy Diseases 0.000 claims description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 2
- 206010018429 Glucose tolerance impaired Diseases 0.000 claims description 2
- 102000004877 Insulin Human genes 0.000 claims description 2
- 108090001061 Insulin Proteins 0.000 claims description 2
- 239000000654 additive Substances 0.000 claims description 2
- 230000001476 alcoholic effect Effects 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 201000006549 dyspepsia Diseases 0.000 claims description 2
- 239000008103 glucose Substances 0.000 claims description 2
- 208000006454 hepatitis Diseases 0.000 claims description 2
- 231100000283 hepatitis Toxicity 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 150000004677 hydrates Chemical class 0.000 claims description 2
- 208000006575 hypertriglyceridemia Diseases 0.000 claims description 2
- 229940125396 insulin Drugs 0.000 claims description 2
- 230000001079 digestive effect Effects 0.000 claims 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 claims 1
- 235000019260 propionic acid Nutrition 0.000 claims 1
- XSYBAAIOZPEMDE-UHFFFAOYSA-N 3-[2-[2-fluoro-5-(trifluoromethoxy)phenyl]-1,3,4,5-tetrahydro-2-benzazepin-7-yl]propanoic acid Chemical compound FC1=C(C=C(C=C1)OC(F)(F)F)N1CC2=C(CCC1)C=C(C=C2)CCC(=O)O XSYBAAIOZPEMDE-UHFFFAOYSA-N 0.000 description 2
- PSLUFJFHTBIXMW-WYEYVKMPSA-N [(3r,4ar,5s,6s,6as,10s,10ar,10bs)-3-ethenyl-10,10b-dihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-6-(2-pyridin-2-ylethylcarbamoyloxy)-5,6,6a,8,9,10-hexahydro-2h-benzo[f]chromen-5-yl] acetate Chemical compound O([C@@H]1[C@@H]([C@]2(O[C@](C)(CC(=O)[C@]2(O)[C@@]2(C)[C@@H](O)CCC(C)(C)[C@@H]21)C=C)C)OC(=O)C)C(=O)NCCC1=CC=CC=N1 PSLUFJFHTBIXMW-WYEYVKMPSA-N 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1704714.3 | 2017-03-24 | ||
| GBGB1704714.3A GB201704714D0 (en) | 2017-03-24 | 2017-03-24 | Pharmaceutical compounds |
| PCT/GB2018/000047 WO2018172727A1 (en) | 2017-03-24 | 2018-03-26 | Tetrahydro-benzo[d]azepine derivatives as gpr120 modulators |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2020515636A JP2020515636A (ja) | 2020-05-28 |
| JP2020515636A5 true JP2020515636A5 (https=) | 2021-04-15 |
| JP7099672B2 JP7099672B2 (ja) | 2022-07-12 |
Family
ID=58687800
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020501850A Active JP7099672B2 (ja) | 2017-03-24 | 2018-03-26 | 医薬化合物 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US11220483B2 (https=) |
| EP (1) | EP3601229B1 (https=) |
| JP (1) | JP7099672B2 (https=) |
| KR (1) | KR102636166B1 (https=) |
| CN (1) | CN110891938B (https=) |
| AU (1) | AU2018238102B2 (https=) |
| BR (1) | BR112019019868A2 (https=) |
| CA (1) | CA3057415A1 (https=) |
| GB (1) | GB201704714D0 (https=) |
| MX (1) | MX394818B (https=) |
| WO (1) | WO2018172727A1 (https=) |
| ZA (1) | ZA201906873B (https=) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR102018007822A2 (pt) | 2017-04-20 | 2018-11-06 | Gilead Sciences, Inc. | composto, métodos para inibir pd-1, pd-l1 e/ou interação de pd-1/pd-l1 e para tratamento de câncer, composição farmacêutica, e, kit para tratamento de ou prevenção de câncer ou uma doença ou condição |
| TWI707849B (zh) | 2018-02-13 | 2020-10-21 | 美商基利科學股份有限公司 | Pd‐1/pd‐l1抑制劑 |
| KR102591947B1 (ko) | 2018-04-19 | 2023-10-25 | 길리애드 사이언시즈, 인코포레이티드 | Pd-1/pd-l1 억제제 |
| EP3820572B1 (en) | 2018-07-13 | 2023-08-16 | Gilead Sciences, Inc. | Pd-1/pd-l1 inhibitors |
| US11236085B2 (en) | 2018-10-24 | 2022-02-01 | Gilead Sciences, Inc. | PD-1/PD-L1 inhibitors |
| JP2022552655A (ja) | 2019-10-07 | 2022-12-19 | キャリーオペ，インク． | Ｇｐｒ１１９アゴニスト |
| IL295825A (en) | 2020-02-28 | 2022-10-01 | Kallyope Inc | gpr40 agonists |
| WO2021236617A1 (en) | 2020-05-19 | 2021-11-25 | Kallyope, Inc. | Ampk activators |
| CA3183575A1 (en) | 2020-06-26 | 2021-12-30 | Iyassu Sebhat | Ampk activators |
| CN114163426B (zh) * | 2020-09-10 | 2024-03-19 | 上海爱博医药科技有限公司 | 苯并含氧杂环类化合物及其医药应用 |
| WO2022076503A1 (en) * | 2020-10-08 | 2022-04-14 | Eli Lilly And Company | 6-methoxy-3,4-dihydro-1h-isoquinoline compounds useful in the treatment of diabetes |
| CN114671827B (zh) * | 2020-12-24 | 2024-09-20 | 杭州百新生物医药科技有限公司 | 邻苯甲酰磺酰亚胺类衍生物及其应用 |
| KR102605163B1 (ko) * | 2021-06-01 | 2023-11-23 | 연세대학교 산학협력단 | 뇌암의 예방 또는 치료용 조성물 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2005282721A1 (en) * | 2004-09-03 | 2006-03-16 | Memory Pharmaceuticals Corporation | 4-substituted 4, 6-dialkoxy-cinnoline derivatives as phospodiesterase 10 inhibitors for the treatment of psychiatric or neurological syndroms |
| AU2006279548A1 (en) | 2005-08-16 | 2007-02-22 | Amgen, Inc. | Phosphodiesterase 10 inhibitors |
| CA2627682A1 (en) | 2006-01-30 | 2007-08-09 | Irm Llc | Polycyclic 1, 2, 3, 4 -tetrahydro- isoquinoline derivatives and compositions comprising them as ppar modulators |
| ATE528306T1 (de) * | 2006-11-02 | 2011-10-15 | Piramal Life Sciences Ltd | Benzoxazepin-verbindungen, ihre herstellung und verwendung |
| JP2010519258A (ja) | 2007-02-22 | 2010-06-03 | アイアールエム・リミテッド・ライアビリティ・カンパニー | Ｇタンパク質共役受容体のモジュレーターとしてのチアゾール誘導体 |
| WO2009147990A1 (ja) * | 2008-06-02 | 2009-12-10 | 萬有製薬株式会社 | 新規イソオキサゾール誘導体 |
| EP2736330A4 (en) | 2011-07-29 | 2015-05-27 | Tempero Pharmaceuticals Inc | COMPOUNDS AND METHODS |
| US10662171B2 (en) | 2014-08-08 | 2020-05-26 | Merck Sharp & Dohme Corp. | Antidiabetic bicyclic compounds |
| WO2016022446A1 (en) | 2014-08-08 | 2016-02-11 | Merck Sharp & Dohme Corp. | [5,6]-fused bicyclic antidiabetic compounds |
| AU2015367977B9 (en) * | 2014-12-24 | 2020-02-06 | Lg Chem, Ltd | Biaryl derivative as GPR120 agonist |
| WO2017201683A1 (en) | 2016-05-25 | 2017-11-30 | Merck Sharp & Dohme Corp. | Substituted tetrahydroisoquinoline compounds useful as gpr120 agonists |
-
2017
- 2017-03-24 GB GBGB1704714.3A patent/GB201704714D0/en not_active Ceased
-
2018
- 2018-03-26 EP EP18715236.8A patent/EP3601229B1/en active Active
- 2018-03-26 AU AU2018238102A patent/AU2018238102B2/en active Active
- 2018-03-26 JP JP2020501850A patent/JP7099672B2/ja active Active
- 2018-03-26 WO PCT/GB2018/000047 patent/WO2018172727A1/en not_active Ceased
- 2018-03-26 CA CA3057415A patent/CA3057415A1/en active Pending
- 2018-03-26 CN CN201880033700.7A patent/CN110891938B/zh not_active Expired - Fee Related
- 2018-03-26 KR KR1020197031368A patent/KR102636166B1/ko active Active
- 2018-03-26 US US16/496,786 patent/US11220483B2/en active Active
- 2018-03-26 MX MX2019011314A patent/MX394818B/es unknown
- 2018-03-26 BR BR112019019868A patent/BR112019019868A2/pt not_active Application Discontinuation
-
2019
- 2019-10-18 ZA ZA2019/06873A patent/ZA201906873B/en unknown
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