CA2941824C - Substituted phenylamino-oxazole-4-carboxylic acid amides as tyk2 kinase inhibitors - Google Patents
Substituted phenylamino-oxazole-4-carboxylic acid amides as tyk2 kinase inhibitors Download PDFInfo
- Publication number
- CA2941824C CA2941824C CA2941824A CA2941824A CA2941824C CA 2941824 C CA2941824 C CA 2941824C CA 2941824 A CA2941824 A CA 2941824A CA 2941824 A CA2941824 A CA 2941824A CA 2941824 C CA2941824 C CA 2941824C
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- Prior art keywords
- disease
- condition
- compound according
- compound
- oxazole
- 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 abstract 35
- 150000003839 salts Chemical class 0.000 claims abstract 16
- 239000011737 fluorine Chemical group 0.000 claims abstract 11
- 229910052731 fluorine Chemical group 0.000 claims abstract 11
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract 10
- 239000000460 chlorine Substances 0.000 claims abstract 10
- 229910052801 chlorine Inorganic materials 0.000 claims abstract 10
- 239000001257 hydrogen Substances 0.000 claims abstract 10
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 10
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract 7
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract 3
- -1 isopropylsulfonyl Chemical group 0.000 claims abstract 3
- 150000001408 amides Chemical class 0.000 claims abstract 2
- 125000006125 ethylsulfonyl group Chemical group 0.000 claims abstract 2
- 150000002431 hydrogen Chemical class 0.000 claims abstract 2
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 2
- 201000010099 disease Diseases 0.000 claims 39
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 39
- 206010052779 Transplant rejections Diseases 0.000 claims 12
- 208000009329 Graft vs Host Disease Diseases 0.000 claims 9
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 9
- 208000024908 graft versus host disease Diseases 0.000 claims 9
- 208000023275 Autoimmune disease Diseases 0.000 claims 6
- 208000003556 Dry Eye Syndromes Diseases 0.000 claims 6
- 206010013774 Dry eye Diseases 0.000 claims 6
- 101000844245 Homo sapiens Non-receptor tyrosine-protein kinase TYK2 Proteins 0.000 claims 6
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 6
- 102100032028 Non-receptor tyrosine-protein kinase TYK2 Human genes 0.000 claims 6
- 208000026935 allergic disease Diseases 0.000 claims 6
- 208000026278 immune system disease Diseases 0.000 claims 6
- 208000027866 inflammatory disease Diseases 0.000 claims 6
- 230000005764 inhibitory process Effects 0.000 claims 6
- 201000010065 polycystic ovary syndrome Diseases 0.000 claims 6
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 4
- 208000026872 Addison Disease Diseases 0.000 claims 3
- 206010002556 Ankylosing Spondylitis Diseases 0.000 claims 3
- 208000023328 Basedow disease Diseases 0.000 claims 3
- 206010008909 Chronic Hepatitis Diseases 0.000 claims 3
- 208000015943 Coeliac disease Diseases 0.000 claims 3
- 201000004624 Dermatitis Diseases 0.000 claims 3
- 208000015023 Graves' disease Diseases 0.000 claims 3
- 208000030836 Hashimoto thyroiditis Diseases 0.000 claims 3
- 206010019755 Hepatitis chronic active Diseases 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 208000009319 Keratoconjunctivitis Sicca Diseases 0.000 claims 3
- 108091000080 Phosphotransferase Proteins 0.000 claims 3
- 208000010067 Pituitary ACTH Hypersecretion Diseases 0.000 claims 3
- 208000020627 Pituitary-dependent Cushing syndrome Diseases 0.000 claims 3
- 201000004681 Psoriasis Diseases 0.000 claims 3
- 206010040047 Sepsis Diseases 0.000 claims 3
- 206010040070 Septic Shock Diseases 0.000 claims 3
- 108010010057 TYK2 Kinase Proteins 0.000 claims 3
- 102000015774 TYK2 Kinase Human genes 0.000 claims 3
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims 3
- 206010046851 Uveitis Diseases 0.000 claims 3
- 210000004100 adrenal gland Anatomy 0.000 claims 3
- 230000009285 allergic inflammation Effects 0.000 claims 3
- 208000006673 asthma Diseases 0.000 claims 3
- 208000037976 chronic inflammation Diseases 0.000 claims 3
- 230000006020 chronic inflammation Effects 0.000 claims 3
- 208000025302 chronic primary adrenal insufficiency Diseases 0.000 claims 3
- 230000000694 effects Effects 0.000 claims 3
- 230000002757 inflammatory effect Effects 0.000 claims 3
- 210000004185 liver Anatomy 0.000 claims 3
- 230000001404 mediated effect Effects 0.000 claims 3
- 201000006417 multiple sclerosis Diseases 0.000 claims 3
- 206010028417 myasthenia gravis Diseases 0.000 claims 3
- 102000020233 phosphotransferase Human genes 0.000 claims 3
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 3
- 230000036303 septic shock Effects 0.000 claims 3
- 208000011580 syndromic disease Diseases 0.000 claims 3
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 2
- 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- KUMWERTZYYEHSV-UHFFFAOYSA-N 2-(2,5-difluorophenyl)-5-(4-methylsulfonylanilino)-1,3-oxazole-4-carboxamide Chemical compound C1=CC(S(=O)(=O)C)=CC=C1NC1=C(C(N)=O)N=C(C=2C(=CC=C(F)C=2)F)O1 KUMWERTZYYEHSV-UHFFFAOYSA-N 0.000 claims 1
- GPSWUDJBYRLTRW-UHFFFAOYSA-N 2-(2,6-dichlorophenyl)-5-[4-(morpholine-4-carbonyl)anilino]-1,3-oxazole-4-carboxamide Chemical compound NC(=O)C=1N=C(C=2C(=CC=CC=2Cl)Cl)OC=1NC(C=C1)=CC=C1C(=O)N1CCOCC1 GPSWUDJBYRLTRW-UHFFFAOYSA-N 0.000 claims 1
- LPYWGQFKWKJYDB-UHFFFAOYSA-N 2-(2,6-dichlorophenyl)-5-[4-[(1-methylpiperidin-4-yl)carbamoyl]anilino]-1,3-oxazole-4-carboxamide Chemical compound C1CN(C)CCC1NC(=O)C(C=C1)=CC=C1NC1=C(C(N)=O)N=C(C=2C(=CC=CC=2Cl)Cl)O1 LPYWGQFKWKJYDB-UHFFFAOYSA-N 0.000 claims 1
- OLKSZFBBMNHFRV-CQSZACIVSA-N 2-(2,6-dichlorophenyl)-5-[4-[[(3r)-piperidin-3-yl]carbamoyl]anilino]-1,3-oxazole-4-carboxamide Chemical compound NC(=O)C=1N=C(C=2C(=CC=CC=2Cl)Cl)OC=1NC(C=C1)=CC=C1C(=O)N[C@@H]1CCCNC1 OLKSZFBBMNHFRV-CQSZACIVSA-N 0.000 claims 1
- OLKSZFBBMNHFRV-AWEZNQCLSA-N 2-(2,6-dichlorophenyl)-5-[4-[[(3s)-piperidin-3-yl]carbamoyl]anilino]-1,3-oxazole-4-carboxamide Chemical compound NC(=O)C=1N=C(C=2C(=CC=CC=2Cl)Cl)OC=1NC(C=C1)=CC=C1C(=O)N[C@H]1CCCNC1 OLKSZFBBMNHFRV-AWEZNQCLSA-N 0.000 claims 1
- VAWFTMZJZHXRFN-UHFFFAOYSA-N 2-(2,6-difluorophenyl)-5-(4-ethylsulfonylanilino)-1,3-oxazole-4-carboxamide Chemical compound C1=CC(S(=O)(=O)CC)=CC=C1NC1=C(C(N)=O)N=C(C=2C(=CC=CC=2F)F)O1 VAWFTMZJZHXRFN-UHFFFAOYSA-N 0.000 claims 1
- BHDQJSFICYHNKA-UHFFFAOYSA-N 2-(2-chloro-6-fluorophenyl)-5-(4-methylsulfonylanilino)-1,3-oxazole-4-carboxamide Chemical compound C1=CC(S(=O)(=O)C)=CC=C1NC1=C(C(N)=O)N=C(C=2C(=CC=CC=2F)Cl)O1 BHDQJSFICYHNKA-UHFFFAOYSA-N 0.000 claims 1
- HEDPDFHTQKEORT-UHFFFAOYSA-N 2-(2-chloro-6-fluorophenyl)-5-[4-(morpholine-4-carbonyl)anilino]-1,3-oxazole-4-carboxamide Chemical compound NC(=O)C=1N=C(C=2C(=CC=CC=2F)Cl)OC=1NC(C=C1)=CC=C1C(=O)N1CCOCC1 HEDPDFHTQKEORT-UHFFFAOYSA-N 0.000 claims 1
- BGJWNODSJDKPEG-UHFFFAOYSA-N 2-(2-chloro-6-fluorophenyl)-5-[4-[(1-methylpiperidin-4-yl)carbamoyl]anilino]-1,3-oxazole-4-carboxamide Chemical compound C1CN(C)CCC1NC(=O)C(C=C1)=CC=C1NC1=C(C(N)=O)N=C(C=2C(=CC=CC=2F)Cl)O1 BGJWNODSJDKPEG-UHFFFAOYSA-N 0.000 claims 1
- XJIZKYUARXWFSC-CQSZACIVSA-N 2-(2-chloro-6-fluorophenyl)-5-[4-[[(3r)-piperidin-3-yl]carbamoyl]anilino]-1,3-oxazole-4-carboxamide Chemical compound NC(=O)C=1N=C(C=2C(=CC=CC=2F)Cl)OC=1NC(C=C1)=CC=C1C(=O)N[C@@H]1CCCNC1 XJIZKYUARXWFSC-CQSZACIVSA-N 0.000 claims 1
- PWKNMZKSSBJPFN-UHFFFAOYSA-N 5-(4-methylsulfonylanilino)-2-(2,4,6-trifluorophenyl)-1,3-oxazole-4-carboxamide Chemical compound C1=CC(S(=O)(=O)C)=CC=C1NC1=C(C(N)=O)N=C(C=2C(=CC(F)=CC=2F)F)O1 PWKNMZKSSBJPFN-UHFFFAOYSA-N 0.000 claims 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- 125000002618 bicyclic heterocycle group Chemical group 0.000 abstract 2
- 125000005842 heteroatom Chemical group 0.000 abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract 2
- 229910052760 oxygen Inorganic materials 0.000 abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 125000002837 carbocyclic group Chemical group 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
- 230000001225 therapeutic effect Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D263/48—Nitrogen atoms not forming part of a nitro radical
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/42—Oxazoles
- A61K31/421—1,3-Oxazoles, e.g. pemoline, trimethadione
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- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
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- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/5005—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving human or animal cells
- G01N33/5008—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving human or animal cells for testing or evaluating the effect of chemical or biological compounds, e.g. drugs, cosmetics
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N2800/00—Detection or diagnosis of diseases
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- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Immunology (AREA)
- Biomedical Technology (AREA)
- Epidemiology (AREA)
- Diabetes (AREA)
- Urology & Nephrology (AREA)
- Hematology (AREA)
- Endocrinology (AREA)
- Pulmonology (AREA)
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Applications Claiming Priority (1)
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| PCT/EP2013/068198 WO2015032423A1 (en) | 2013-09-03 | 2013-09-03 | Pharmaceutical compounds |
Publications (2)
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| CA2941824A1 CA2941824A1 (en) | 2015-03-12 |
| CA2941824C true CA2941824C (en) | 2020-08-25 |
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| CA2941824A Active CA2941824C (en) | 2013-09-03 | 2013-09-03 | Substituted phenylamino-oxazole-4-carboxylic acid amides as tyk2 kinase inhibitors |
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| Country | Link |
|---|---|
| JP (1) | JP6239118B2 (enExample) |
| KR (1) | KR102191084B1 (enExample) |
| CN (1) | CN105793245B (enExample) |
| AU (1) | AU2013399913B2 (enExample) |
| BR (1) | BR112016004723B1 (enExample) |
| CA (1) | CA2941824C (enExample) |
| IL (1) | IL244380B (enExample) |
| MX (1) | MX369974B (enExample) |
| RU (1) | RU2652795C2 (enExample) |
| SG (1) | SG11201601503SA (enExample) |
| WO (1) | WO2015032423A1 (enExample) |
| ZA (1) | ZA201602047B (enExample) |
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| GB201617871D0 (en) | 2016-10-21 | 2016-12-07 | Sareum Limited | Pharmaceutical compounds |
| WO2019132654A1 (en) * | 2017-12-27 | 2019-07-04 | Erasmus University Medical Center Rotterdam | Methods of treating sarcoidosis |
| WO2020009566A1 (en) * | 2018-07-04 | 2020-01-09 | Erasmus University Medical Center Rotterdam | Methods of treating sarcoidosis |
| GB201816369D0 (en) | 2018-10-08 | 2018-11-28 | Sareum Ltd | Pharmaceutical compounds |
| MX2021013317A (es) | 2019-04-30 | 2022-01-18 | Celgene Corp | Terapias de combinacion que comprenden inhibidores de apremilast y tyk2. |
| GB202005114D0 (en) | 2020-04-07 | 2020-05-20 | Sareum Ltd | Crystalline Forms of a Pharmaceutical Compound |
| EP3944859A1 (en) | 2020-07-30 | 2022-02-02 | Assistance Publique Hôpitaux de Paris | Method for treating immune toxicities induced by immune checkpoint inhibitors |
| JP2024535467A (ja) | 2021-09-30 | 2024-09-30 | ブリストル－マイヤーズ スクイブ カンパニー | Ｔｙｋ２阻害剤に対する応答性を決定する方法 |
| CN119013277A (zh) | 2021-10-25 | 2024-11-22 | 凯麦拉医疗公司 | Tyk2降解剂和其用途 |
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| GB1497536A (en) * | 1973-12-17 | 1978-01-12 | Lilly Industries Ltd | 2-acylaminooxazoles methods for their preparation and their use |
| KR100404256B1 (ko) * | 1998-05-05 | 2003-11-01 | 에프. 호프만-라 로슈 아게 | 피-38 엠에이피 키나제 저해제로서의 피라졸 유도체 |
| GB0709031D0 (en) * | 2007-05-10 | 2007-06-20 | Sareum Ltd | Pharmaceutical compounds |
| AU2008266883B2 (en) | 2007-06-20 | 2014-01-30 | Merck Sharp & Dohme Corp. | Inhibitors of janus kinases |
| CA2719847A1 (en) | 2008-04-21 | 2010-01-28 | Merck Sharp & Dohme Corp. | Inhibitors of janus kinases |
| US8344144B2 (en) | 2008-06-18 | 2013-01-01 | Merck Sharp & Dohme Corp. | Inhibitors of Janus kinases |
| JP2011527680A (ja) | 2008-07-09 | 2011-11-04 | メルク・シャープ・エンド・ドーム・コーポレイション | Ｊａｎｕｓキナーゼの阻害剤 |
| EP2166006A1 (en) * | 2008-09-18 | 2010-03-24 | Dompe' S.P.A. | 2-aryl-propionic acids and derivatives and pharmaceutical compositions containing them |
| GB0820819D0 (en) * | 2008-11-13 | 2008-12-24 | Sareum Ltd | Pharmaceutical compounds |
| WO2011113802A2 (en) | 2010-03-17 | 2011-09-22 | F. Hoffmann-La Roche Ag | Imidazopyridine compounds, compositions and methods of use |
| WO2012000970A1 (en) | 2010-07-01 | 2012-01-05 | Cellzome Limited | Triazolopyridines as tyk2 inhibitors |
| SG11201401342VA (en) * | 2011-10-12 | 2014-09-26 | Array Biopharma Inc | 5,7-substituted-imidazo[1,2-c]pyrimidines |
| PL2634185T3 (pl) * | 2012-03-02 | 2016-06-30 | Sareum Ltd | Inhibitory kinazy TYK2 |
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2013
- 2013-09-03 KR KR1020167007925A patent/KR102191084B1/ko active Active
- 2013-09-03 BR BR112016004723-0A patent/BR112016004723B1/pt active IP Right Grant
- 2013-09-03 JP JP2016537144A patent/JP6239118B2/ja active Active
- 2013-09-03 MX MX2016002738A patent/MX369974B/es active IP Right Grant
- 2013-09-03 CN CN201380080517.XA patent/CN105793245B/zh active Active
- 2013-09-03 WO PCT/EP2013/068198 patent/WO2015032423A1/en not_active Ceased
- 2013-09-03 SG SG11201601503SA patent/SG11201601503SA/en unknown
- 2013-09-03 RU RU2016111522A patent/RU2652795C2/ru active
- 2013-09-03 AU AU2013399913A patent/AU2013399913B2/en active Active
- 2013-09-03 CA CA2941824A patent/CA2941824C/en active Active
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2016
- 2016-03-02 IL IL244380A patent/IL244380B/en active IP Right Grant
- 2016-03-29 ZA ZA2016/02047A patent/ZA201602047B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| KR20160048883A (ko) | 2016-05-04 |
| WO2015032423A1 (en) | 2015-03-12 |
| ZA201602047B (en) | 2020-12-23 |
| JP2016529264A (ja) | 2016-09-23 |
| IL244380B (en) | 2018-01-31 |
| RU2652795C2 (ru) | 2018-05-03 |
| BR112016004723A2 (enExample) | 2017-08-01 |
| SG11201601503SA (en) | 2016-03-30 |
| AU2013399913B2 (en) | 2018-03-15 |
| KR102191084B1 (ko) | 2020-12-15 |
| RU2016111522A (ru) | 2017-10-09 |
| CA2941824A1 (en) | 2015-03-12 |
| JP6239118B2 (ja) | 2017-11-29 |
| IL244380A0 (en) | 2016-04-21 |
| MX2016002738A (es) | 2016-08-11 |
| CN105793245B (zh) | 2018-03-20 |
| BR112016004723B1 (pt) | 2022-08-30 |
| AU2013399913A1 (en) | 2016-03-24 |
| MX369974B (es) | 2019-11-27 |
| CN105793245A (zh) | 2016-07-20 |
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Effective date: 20180802 |