CA2921634A1 - Multivalent sialic acid derivates - Google Patents
Multivalent sialic acid derivates Download PDFInfo
- Publication number
- CA2921634A1 CA2921634A1 CA2921634A CA2921634A CA2921634A1 CA 2921634 A1 CA2921634 A1 CA 2921634A1 CA 2921634 A CA2921634 A CA 2921634A CA 2921634 A CA2921634 A CA 2921634A CA 2921634 A1 CA2921634 A1 CA 2921634A1
- Authority
- CA
- Canada
- Prior art keywords
- sialic acid
- groups
- formula
- acid derivate
- pharmaceutical composition
- 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.)
- Abandoned
Links
- SQVRNKJHWKZAKO-OQPLDHBCSA-N sialic acid Chemical compound CC(=O)N[C@@H]1[C@@H](O)C[C@@](O)(C(O)=O)OC1[C@H](O)[C@H](O)CO SQVRNKJHWKZAKO-OQPLDHBCSA-N 0.000 title claims abstract description 110
- SQVRNKJHWKZAKO-UHFFFAOYSA-N beta-N-Acetyl-D-neuraminic acid Natural products CC(=O)NC1C(O)CC(O)(C(O)=O)OC1C(O)C(O)CO SQVRNKJHWKZAKO-UHFFFAOYSA-N 0.000 title claims description 90
- 208000015181 infectious disease Diseases 0.000 claims abstract description 31
- 208000021373 epidemic keratoconjunctivitis Diseases 0.000 claims abstract description 23
- 201000006476 shipyard eye Diseases 0.000 claims abstract description 23
- 206010001257 Adenoviral conjunctivitis Diseases 0.000 claims abstract description 21
- 239000000203 mixture Substances 0.000 claims description 58
- 239000008194 pharmaceutical composition Substances 0.000 claims description 56
- 150000001875 compounds Chemical class 0.000 claims description 55
- 210000004027 cell Anatomy 0.000 claims description 52
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 49
- 239000007983 Tris buffer Substances 0.000 claims description 35
- 239000002253 acid Substances 0.000 claims description 34
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 claims description 34
- 229910001868 water Inorganic materials 0.000 claims description 30
- 241000700605 Viruses Species 0.000 claims description 26
- 150000001412 amines Chemical class 0.000 claims description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 17
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 15
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- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 230000002265 prevention Effects 0.000 claims description 9
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- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
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- 229910052717 sulfur Inorganic materials 0.000 claims description 6
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- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
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- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 12
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- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 11
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 235000014633 carbohydrates Nutrition 0.000 description 9
- 125000005647 linker group Chemical group 0.000 description 9
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 8
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 8
- WMFOQBRAJBCJND-UHFFFAOYSA-M lithium hydroxide Inorganic materials [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 8
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
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- 235000019253 formic acid Nutrition 0.000 description 7
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- 230000003389 potentiating effect Effects 0.000 description 7
- -1 sialic acid monosaccharide Chemical class 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 238000002198 surface plasmon resonance spectroscopy Methods 0.000 description 7
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- 230000008878 coupling Effects 0.000 description 6
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- 239000000499 gel Substances 0.000 description 6
- ZHOBJWVNWMQMLF-UHFFFAOYSA-N n,n-bis(prop-2-ynyl)prop-2-yn-1-amine Chemical compound C#CCN(CC#C)CC#C ZHOBJWVNWMQMLF-UHFFFAOYSA-N 0.000 description 6
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- 239000011734 sodium Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
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- 125000002947 alkylene group Chemical group 0.000 description 5
- 150000001540 azides Chemical class 0.000 description 5
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 5
- 229910000366 copper(II) sulfate Inorganic materials 0.000 description 5
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 5
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 5
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- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 5
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- PWEBUXCTKOWPCW-UHFFFAOYSA-N squaric acid Chemical compound OC1=C(O)C(=O)C1=O PWEBUXCTKOWPCW-UHFFFAOYSA-N 0.000 description 4
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- FANCTJAFZSYTIS-IQUVVAJASA-N (1r,3s,5z)-5-[(2e)-2-[(1r,3as,7ar)-7a-methyl-1-[(2r)-4-(phenylsulfonimidoyl)butan-2-yl]-2,3,3a,5,6,7-hexahydro-1h-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol Chemical compound C([C@@H](C)[C@@H]1[C@]2(CCCC(/[C@@H]2CC1)=C\C=C\1C([C@@H](O)C[C@H](O)C/1)=C)C)CS(=N)(=O)C1=CC=CC=C1 FANCTJAFZSYTIS-IQUVVAJASA-N 0.000 description 3
- SHAHPWSYJFYMRX-GDLCADMTSA-N (2S)-2-(4-{[(1R,2S)-2-hydroxycyclopentyl]methyl}phenyl)propanoic acid Chemical compound C1=CC([C@@H](C(O)=O)C)=CC=C1C[C@@H]1[C@@H](O)CCC1 SHAHPWSYJFYMRX-GDLCADMTSA-N 0.000 description 3
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- 229960004194 lidocaine Drugs 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 229960005015 local anesthetics Drugs 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
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- 238000001819 mass spectrum Methods 0.000 description 1
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- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
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- 235000010981 methylcellulose Nutrition 0.000 description 1
- 229960002216 methylparaben Drugs 0.000 description 1
- 230000003641 microbiacidal effect Effects 0.000 description 1
- 210000001616 monocyte Anatomy 0.000 description 1
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- 230000003232 mucoadhesive effect Effects 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 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 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
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- 229940006093 opthalmologic coloring agent diagnostic Drugs 0.000 description 1
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- 229920001277 pectin Polymers 0.000 description 1
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- 229960001179 penciclovir Drugs 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229960005323 phenoxyethanol Drugs 0.000 description 1
- 229940067107 phenylethyl alcohol Drugs 0.000 description 1
- 229920001993 poloxamer 188 Polymers 0.000 description 1
- 229940044519 poloxamer 188 Drugs 0.000 description 1
- 229920001992 poloxamer 407 Polymers 0.000 description 1
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- 239000004584 polyacrylic acid Substances 0.000 description 1
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- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229940069328 povidone Drugs 0.000 description 1
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- 238000002203 pretreatment Methods 0.000 description 1
- 229960001807 prilocaine Drugs 0.000 description 1
- MVFGUOIZUNYYSO-UHFFFAOYSA-N prilocaine Chemical compound CCCNC(C)C(=O)NC1=CC=CC=C1C MVFGUOIZUNYYSO-UHFFFAOYSA-N 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 229960003415 propylparaben Drugs 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
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- 239000011347 resin Substances 0.000 description 1
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- 229960001549 ropivacaine Drugs 0.000 description 1
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- 238000011894 semi-preparative HPLC Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 108010061514 sialic acid receptor Proteins 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
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- 239000001384 succinic acid Substances 0.000 description 1
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- 239000011975 tartaric acid Substances 0.000 description 1
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
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- JQSHBVHOMNKWFT-DTORHVGOSA-N varenicline Chemical compound C12=CC3=NC=CN=C3C=C2[C@H]2C[C@@H]1CNC2 JQSHBVHOMNKWFT-DTORHVGOSA-N 0.000 description 1
- 230000017613 viral reproduction Effects 0.000 description 1
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- 229940082509 xanthan gum Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/26—Acyclic or carbocyclic radicals, substituted by hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
- A61K31/7052—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
- A61K31/7056—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing five-membered rings with nitrogen as a ring hetero atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/08—Solutions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/20—Antivirals for DNA viruses
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Organic Chemistry (AREA)
- Epidemiology (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- Virology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Ophthalmology & Optometry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE1350991-4 | 2013-08-28 | ||
| SE1350991 | 2013-08-28 | ||
| PCT/EP2014/068252 WO2015028548A1 (en) | 2013-08-28 | 2014-08-28 | Multivalent sialic acid derivates |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2921634A1 true CA2921634A1 (en) | 2015-03-05 |
Family
ID=51454687
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2921634A Abandoned CA2921634A1 (en) | 2013-08-28 | 2014-08-28 | Multivalent sialic acid derivates |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US10011628B2 (enExample) |
| EP (1) | EP3039029B1 (enExample) |
| JP (1) | JP6360895B2 (enExample) |
| KR (1) | KR20160073372A (enExample) |
| CN (1) | CN105722849B (enExample) |
| AU (1) | AU2014314212B2 (enExample) |
| CA (1) | CA2921634A1 (enExample) |
| ES (1) | ES2677219T3 (enExample) |
| IL (1) | IL244246B (enExample) |
| MX (1) | MX2016002578A (enExample) |
| PL (1) | PL3039029T3 (enExample) |
| TR (1) | TR201809630T4 (enExample) |
| WO (1) | WO2015028548A1 (enExample) |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE9904289D0 (sv) | 1999-11-26 | 1999-11-26 | Niklas Arnberg | Method and camposition for the treatment of adenovairal ocular infections |
| US20070020620A1 (en) * | 2005-07-14 | 2007-01-25 | Finn M G | Compositions and methods for coupling a plurality of compounds to a scaffold |
| US20080194801A1 (en) * | 2007-02-14 | 2008-08-14 | Swanson Basil I | Robust multidentate ligands for diagnosis and anti-viral drugs for influenza and related viruses |
| BR112012000381A2 (pt) | 2009-07-07 | 2016-03-29 | Adenovir Pharma Ab | novos compostos antivirais úteis para o tratamento ou prevenção de queratoconjuntivite epidêmica |
| KR101217685B1 (ko) | 2010-05-28 | 2013-01-02 | 서강대학교산학협력단 | 서로 다른 실릴기로 보호된 알킨 그룹을 갖는 삼중연결고리 화합물, 이의 제조방법 및 응용 |
| WO2011158068A1 (en) | 2010-06-18 | 2011-12-22 | Centre National De La Recherche Scientifique (Cnrs) | Non covalent molecular structure, device comprising the same and its use for detection of lectin |
-
2014
- 2014-08-28 KR KR1020167007981A patent/KR20160073372A/ko not_active Ceased
- 2014-08-28 WO PCT/EP2014/068252 patent/WO2015028548A1/en not_active Ceased
- 2014-08-28 JP JP2016537292A patent/JP6360895B2/ja not_active Expired - Fee Related
- 2014-08-28 EP EP14758353.8A patent/EP3039029B1/en not_active Not-in-force
- 2014-08-28 MX MX2016002578A patent/MX2016002578A/es unknown
- 2014-08-28 CN CN201480047068.3A patent/CN105722849B/zh not_active Expired - Fee Related
- 2014-08-28 CA CA2921634A patent/CA2921634A1/en not_active Abandoned
- 2014-08-28 TR TR2018/09630T patent/TR201809630T4/tr unknown
- 2014-08-28 AU AU2014314212A patent/AU2014314212B2/en not_active Ceased
- 2014-08-28 US US14/914,988 patent/US10011628B2/en not_active Expired - Fee Related
- 2014-08-28 PL PL14758353T patent/PL3039029T3/pl unknown
- 2014-08-28 ES ES14758353.8T patent/ES2677219T3/es active Active
-
2016
- 2016-02-23 IL IL244246A patent/IL244246B/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| IL244246B (en) | 2019-02-28 |
| KR20160073372A (ko) | 2016-06-24 |
| EP3039029B1 (en) | 2018-04-11 |
| CN105722849B (zh) | 2019-01-29 |
| ES2677219T3 (es) | 2018-07-31 |
| IL244246A0 (en) | 2016-04-21 |
| CN105722849A (zh) | 2016-06-29 |
| WO2015028548A1 (en) | 2015-03-05 |
| US10011628B2 (en) | 2018-07-03 |
| EP3039029A1 (en) | 2016-07-06 |
| MX2016002578A (es) | 2016-09-08 |
| US20160207955A1 (en) | 2016-07-21 |
| AU2014314212A1 (en) | 2016-03-10 |
| AU2014314212B2 (en) | 2018-03-01 |
| PL3039029T3 (pl) | 2018-10-31 |
| JP6360895B2 (ja) | 2018-07-18 |
| JP2016529269A (ja) | 2016-09-23 |
| TR201809630T4 (tr) | 2018-07-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20190826 |
|
| FZDE | Discontinued |
Effective date: 20210304 |