AU2011336266B2 - Novel cyclosporin derivatives for the treatment and prevention of a viral infection - Google Patents
Novel cyclosporin derivatives for the treatment and prevention of a viral infection Download PDFInfo
- Publication number
- AU2011336266B2 AU2011336266B2 AU2011336266A AU2011336266A AU2011336266B2 AU 2011336266 B2 AU2011336266 B2 AU 2011336266B2 AU 2011336266 A AU2011336266 A AU 2011336266A AU 2011336266 A AU2011336266 A AU 2011336266A AU 2011336266 B2 AU2011336266 B2 AU 2011336266B2
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- Australia
- Prior art keywords
- alkyl
- hydroxy
- cyclosporin
- optionally substituted
- sar
- Prior art date
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- 208000036142 Viral infection Diseases 0.000 title claims abstract description 18
- 230000009385 viral infection Effects 0.000 title claims abstract description 18
- PMATZTZNYRCHOR-CGLBZJNRSA-N Cyclosporin A Chemical class CC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O PMATZTZNYRCHOR-CGLBZJNRSA-N 0.000 title description 24
- 238000011282 treatment Methods 0.000 title description 9
- 230000002265 prevention Effects 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 171
- 150000003839 salts Chemical class 0.000 claims abstract description 56
- 238000000034 method Methods 0.000 claims abstract description 41
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 342
- 229960001265 ciclosporin Drugs 0.000 claims description 302
- -1 (E)-but-2-enyl Chemical group 0.000 claims description 203
- 150000002367 halogens Chemical class 0.000 claims description 177
- 229910052736 halogen Inorganic materials 0.000 claims description 170
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 154
- 125000003118 aryl group Chemical group 0.000 claims description 114
- 125000000623 heterocyclic group Chemical group 0.000 claims description 112
- 229910052757 nitrogen Inorganic materials 0.000 claims description 109
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 102
- 108010036949 Cyclosporine Proteins 0.000 claims description 90
- 229930105110 Cyclosporin A Natural products 0.000 claims description 88
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 87
- 229930182912 cyclosporin Natural products 0.000 claims description 84
- 229910052717 sulfur Inorganic materials 0.000 claims description 81
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 76
- 229910052760 oxygen Inorganic materials 0.000 claims description 73
- 229910052739 hydrogen Inorganic materials 0.000 claims description 71
- 239000001257 hydrogen Substances 0.000 claims description 71
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 64
- 125000005842 heteroatom Chemical group 0.000 claims description 63
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 59
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 59
- 239000011593 sulfur Substances 0.000 claims description 58
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 57
- 239000001301 oxygen Substances 0.000 claims description 57
- 229920006395 saturated elastomer Polymers 0.000 claims description 57
- 125000006413 ring segment Chemical group 0.000 claims description 55
- 125000003342 alkenyl group Chemical group 0.000 claims description 50
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 49
- 125000001424 substituent group Chemical group 0.000 claims description 46
- 125000000304 alkynyl group Chemical group 0.000 claims description 41
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 40
- 229910003827 NRaRb Inorganic materials 0.000 claims description 40
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 39
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 37
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 34
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 32
- 229910052701 rubidium Inorganic materials 0.000 claims description 32
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 31
- 229910052705 radium Inorganic materials 0.000 claims description 27
- 241000894007 species Species 0.000 claims description 26
- 125000003282 alkyl amino group Chemical group 0.000 claims description 24
- 239000003814 drug Substances 0.000 claims description 23
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 23
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 21
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 16
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 16
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 claims description 14
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 14
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 13
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 150000001412 amines Chemical class 0.000 claims description 10
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- 238000002360 preparation method Methods 0.000 claims description 10
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 8
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- 208000010710 hepatitis C virus infection Diseases 0.000 claims description 6
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 6
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims description 5
- 208000031886 HIV Infections Diseases 0.000 claims description 5
- 208000037357 HIV infectious disease Diseases 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 5
- 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 claims description 5
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 4
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims description 3
- 208000005176 Hepatitis C Diseases 0.000 claims description 3
- MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 claims description 3
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 447
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- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 291
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 204
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 135
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 134
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- SGOIRFVFHAKUTI-ZCFIWIBFSA-N tenofovir (anhydrous) Chemical compound N1=CN=C2N(C[C@@H](C)OCP(O)(O)=O)C=NC2=C1N SGOIRFVFHAKUTI-ZCFIWIBFSA-N 0.000 description 1
- BNWCETAHAJSBFG-UHFFFAOYSA-N tert-butyl 2-bromoacetate Chemical compound CC(C)(C)OC(=O)CBr BNWCETAHAJSBFG-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000006090 thiamorpholinyl sulfone group Chemical group 0.000 description 1
- 125000006089 thiamorpholinyl sulfoxide group Chemical group 0.000 description 1
- 125000001984 thiazolidinyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 150000003567 thiocyanates Chemical class 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- 238000003354 tissue distribution assay Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-M toluenesulfonate group Chemical group C=1(C(=CC=CC1)S(=O)(=O)[O-])C LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
- 125000005490 tosylate group Chemical group 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
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 229940063032 tyzeka Drugs 0.000 description 1
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical class CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000002255 vaccination Methods 0.000 description 1
- 229940070710 valerate Drugs 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 229940086210 victrelis Drugs 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 230000029812 viral genome replication Effects 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/64—Cyclic peptides containing only normal peptide links
- C07K7/645—Cyclosporins; Related peptides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
- A61K38/12—Cyclic peptides, e.g. bacitracins; Polymyxins; Gramicidins S, C; Tyrocidins A, B or C
- A61K38/13—Cyclosporins
-
- 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
- A61P31/14—Antivirals for RNA viruses
-
- 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
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Virology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Molecular Biology (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Communicable Diseases (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Genetics & Genomics (AREA)
- Biophysics (AREA)
- Biochemistry (AREA)
- Engineering & Computer Science (AREA)
- Gastroenterology & Hepatology (AREA)
- Biotechnology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Epidemiology (AREA)
- AIDS & HIV (AREA)
- Tropical Medicine & Parasitology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US41932610P | 2010-12-03 | 2010-12-03 | |
| US61/419,326 | 2010-12-03 | ||
| PCT/US2011/063295 WO2012075494A1 (en) | 2010-12-03 | 2011-12-05 | Novel cyclosporin derivatives for the treatment and prevention of a viral infection |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2011336266A1 AU2011336266A1 (en) | 2013-06-27 |
| AU2011336266B2 true AU2011336266B2 (en) | 2017-04-06 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2011336266A Active AU2011336266B2 (en) | 2010-12-03 | 2011-12-05 | Novel cyclosporin derivatives for the treatment and prevention of a viral infection |
Country Status (13)
| Country | Link |
|---|---|
| EP (1) | EP2646043B1 (enExample) |
| JP (1) | JP6093307B2 (enExample) |
| CN (1) | CN103249424B (enExample) |
| AU (1) | AU2011336266B2 (enExample) |
| BR (1) | BR112013015771A2 (enExample) |
| CA (1) | CA2819608C (enExample) |
| DK (1) | DK2646043T3 (enExample) |
| ES (1) | ES2625502T3 (enExample) |
| MX (1) | MX350746B (enExample) |
| PT (1) | PT2646043T (enExample) |
| RU (1) | RU2601742C2 (enExample) |
| WO (1) | WO2012075494A1 (enExample) |
| ZA (1) | ZA201303610B (enExample) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107007815A (zh) | 2010-07-16 | 2017-08-04 | 美国科技环球有限公司 | 新颖的环孢霉素a衍生物在病毒感染的治疗和预防中的应用 |
| WO2012021796A2 (en) | 2010-08-12 | 2012-02-16 | S&T Global, Inc. | Novel cyclosporin derivatives for the treatment and prevention of a viral infection |
| MX2013004062A (es) | 2010-10-12 | 2013-07-22 | Allergan Inc | Analogos de ciclosporina. |
| RU2013119869A (ru) * | 2010-10-12 | 2014-11-20 | Аллерган, Инк. | Аналоги циклоспорина |
| US9890198B2 (en) | 2010-12-03 | 2018-02-13 | S&T Global Inc. | Cyclosporin derivatives and uses thereof |
| CA2874548A1 (en) | 2012-06-01 | 2013-12-05 | Allergan, Inc. | Cyclosporin a analogs |
| EP2900684A2 (en) * | 2012-09-29 | 2015-08-05 | Novartis AG | Cyclic peptides and use as medicines |
| EP2968445A4 (en) * | 2013-03-15 | 2016-10-12 | Zhuang Su | NOVEL CYCLOSPORINE DERIVATIVES AND USES THEREOF |
| WO2016112321A1 (en) | 2015-01-08 | 2016-07-14 | Allergan, Inc. | Cyclosporin derivatives wherein the mebmt sidechain has been cyclized |
| JP2019518745A (ja) | 2016-05-17 | 2019-07-04 | エス アンド ティー グローバル インク． | 新規シクロスポリン誘導体及びその使用 |
| EP3914655B1 (en) | 2019-01-24 | 2025-04-23 | Agfa Nv | Radiation curable inkjet inks for interior decoration |
| EP3686252A1 (en) | 2019-01-24 | 2020-07-29 | Agfa-Gevaert Nv | Radiation curable inkjet ink for manufacturing printed circuit boards |
| US12226446B2 (en) | 2019-10-11 | 2025-02-18 | Waterstone Pharmaceuticals(Wuhan) Co., Ltd. | WS-635 uses thereof in medicine |
| AU2021256222A1 (en) * | 2020-04-15 | 2022-10-06 | Farsight Medical Technology (Shanghai) Co., Ltd. | Prevention and treatment of organ injuries |
| WO2021243658A1 (en) * | 2020-06-04 | 2021-12-09 | Waterstone Pharmaceuticals (Wuhan) Co., Ltd. | Treatment or prevention of coronaviridae infection |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0194972B1 (en) * | 1985-03-11 | 1992-07-29 | Sandoz Ag | Novel cyclosporins |
| NZ315324A (en) * | 1995-07-17 | 1999-10-28 | Chem Ag C | Cyclosporin derivatives with anti-hiv effect |
| JP2008514702A (ja) * | 2004-09-29 | 2008-05-08 | エーエムアール テクノロジー インコーポレイテッド | 新規シクロスポリン類似体およびそれらの薬学的使用 |
| SI1802650T1 (sl) * | 2004-10-01 | 2012-03-30 | Scynexis Inc | Eter in tioeter substituirani ciklosporinski derivati za zdravljenje in preventivo pred infekcijami s hepatitisom c |
| ZA200703157B (en) * | 2004-10-01 | 2008-08-27 | Scynexis Inc | 3-ether and 3-thioether substituted cyclosporin derivatives for the treatment and prevention of hepatitis C infection |
| US7196161B2 (en) * | 2004-10-01 | 2007-03-27 | Scynexis Inc. | 3-ether and 3-thioether substituted cyclosporin derivatives for the treatment and prevention of hepatitis C infection |
| AU2010203656A1 (en) * | 2009-01-07 | 2011-07-21 | Scynexis, Inc. | Cyclosporine derivative for use in the treatment of HCV and HIV infection |
| EP2391376A4 (en) * | 2009-01-30 | 2012-08-01 | Enanta Pharm Inc | ANALOGUES OF CYCLOSPORIN FOR PREVENTING OR TREATING HEPATITIS C INFECTION |
| WO2012021796A2 (en) * | 2010-08-12 | 2012-02-16 | S&T Global, Inc. | Novel cyclosporin derivatives for the treatment and prevention of a viral infection |
-
2011
- 2011-12-05 AU AU2011336266A patent/AU2011336266B2/en active Active
- 2011-12-05 PT PT118454602T patent/PT2646043T/pt unknown
- 2011-12-05 WO PCT/US2011/063295 patent/WO2012075494A1/en not_active Ceased
- 2011-12-05 CN CN201180058384.7A patent/CN103249424B/zh active Active
- 2011-12-05 RU RU2013130256/04A patent/RU2601742C2/ru active
- 2011-12-05 BR BR112013015771A patent/BR112013015771A2/pt not_active IP Right Cessation
- 2011-12-05 MX MX2013006254A patent/MX350746B/es active IP Right Grant
- 2011-12-05 DK DK11845460.2T patent/DK2646043T3/da active
- 2011-12-05 CA CA2819608A patent/CA2819608C/en active Active
- 2011-12-05 JP JP2013542244A patent/JP6093307B2/ja not_active Expired - Fee Related
- 2011-12-05 ES ES11845460.2T patent/ES2625502T3/es active Active
- 2011-12-05 EP EP11845460.2A patent/EP2646043B1/en active Active
-
2013
- 2013-05-17 ZA ZA2013/03610A patent/ZA201303610B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| MX2013006254A (es) | 2013-10-30 |
| RU2601742C2 (ru) | 2016-11-10 |
| EP2646043B1 (en) | 2017-02-15 |
| AU2011336266A1 (en) | 2013-06-27 |
| CN103249424B (zh) | 2016-08-10 |
| CA2819608C (en) | 2020-03-31 |
| MX350746B (es) | 2017-09-14 |
| JP2014500265A (ja) | 2014-01-09 |
| JP6093307B2 (ja) | 2017-03-08 |
| EP2646043A1 (en) | 2013-10-09 |
| DK2646043T3 (da) | 2017-05-22 |
| BR112013015771A2 (pt) | 2018-11-06 |
| CA2819608A1 (en) | 2012-06-07 |
| RU2013130256A (ru) | 2015-01-10 |
| PT2646043T (pt) | 2017-05-09 |
| EP2646043A4 (en) | 2014-05-28 |
| CN103249424A (zh) | 2013-08-14 |
| ES2625502T3 (es) | 2017-07-19 |
| ZA201303610B (en) | 2014-07-30 |
| WO2012075494A1 (en) | 2012-06-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FGA | Letters patent sealed or granted (standard patent) |