CA2623898C - New cyclic peptide compounds - Google Patents
New cyclic peptide compounds Download PDFInfo
- Publication number
- CA2623898C CA2623898C CA2623898A CA2623898A CA2623898C CA 2623898 C CA2623898 C CA 2623898C CA 2623898 A CA2623898 A CA 2623898A CA 2623898 A CA2623898 A CA 2623898A CA 2623898 C CA2623898 C CA 2623898C
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- Canada
- Prior art keywords
- prep
- brd
- solution
- compound
- salt
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 183
- 108010069514 Cyclic Peptides Proteins 0.000 title claims abstract description 8
- 102000001189 Cyclic Peptides Human genes 0.000 title claims abstract description 8
- 150000003839 salts Chemical class 0.000 claims abstract description 75
- 208000005176 Hepatitis C Diseases 0.000 claims abstract description 15
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 4
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 84
- 238000000034 method Methods 0.000 abstract description 46
- 230000008569 process Effects 0.000 abstract description 28
- 238000002360 preparation method Methods 0.000 abstract description 26
- 230000000694 effects Effects 0.000 abstract description 14
- 150000001413 amino acids Chemical class 0.000 abstract description 11
- 241000700605 Viruses Species 0.000 abstract description 9
- 230000002401 inhibitory effect Effects 0.000 abstract description 7
- 230000010076 replication Effects 0.000 abstract description 7
- 238000006462 rearrangement reaction Methods 0.000 abstract description 4
- 241001465754 Metazoa Species 0.000 abstract description 3
- 230000002378 acidificating effect Effects 0.000 abstract description 3
- 230000001225 therapeutic effect Effects 0.000 abstract description 3
- 241000711549 Hepacivirus C Species 0.000 abstract description 2
- 230000000069 prophylactic effect Effects 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 116
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 73
- 239000000203 mixture Substances 0.000 description 73
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 64
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 56
- 238000001816 cooling Methods 0.000 description 55
- -1 carbamoyloxy Chemical group 0.000 description 52
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 51
- 239000012267 brine Substances 0.000 description 50
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 50
- 125000000217 alkyl group Chemical group 0.000 description 49
- 239000007864 aqueous solution Substances 0.000 description 48
- 239000000843 powder Substances 0.000 description 40
- 239000002904 solvent Substances 0.000 description 38
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 35
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 32
- 125000003545 alkoxy group Chemical group 0.000 description 28
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 28
- 235000019341 magnesium sulphate Nutrition 0.000 description 28
- 239000012074 organic phase Substances 0.000 description 26
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 26
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 25
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- 125000003118 aryl group Chemical group 0.000 description 23
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- 239000007832 Na2SO4 Substances 0.000 description 21
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 21
- 229910052938 sodium sulfate Inorganic materials 0.000 description 21
- 235000011152 sodium sulphate Nutrition 0.000 description 21
- 239000002253 acid Substances 0.000 description 19
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
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- 125000000623 heterocyclic group Chemical group 0.000 description 18
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 18
- 235000017557 sodium bicarbonate Nutrition 0.000 description 18
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 18
- 239000011541 reaction mixture Substances 0.000 description 16
- FPIRBHDGWMWJEP-UHFFFAOYSA-N 1-hydroxy-7-azabenzotriazole Chemical compound C1=CN=C2N(O)N=NC2=C1 FPIRBHDGWMWJEP-UHFFFAOYSA-N 0.000 description 15
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 15
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- 229910052757 nitrogen Inorganic materials 0.000 description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 14
- 125000004433 nitrogen atom Chemical group N* 0.000 description 14
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 13
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical class CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 13
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 13
- 239000012044 organic layer Substances 0.000 description 13
- 239000007787 solid Substances 0.000 description 13
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- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- 239000000741 silica gel Substances 0.000 description 12
- 229910002027 silica gel Inorganic materials 0.000 description 12
- 229960001866 silicon dioxide Drugs 0.000 description 12
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 11
- 125000002911 monocyclic heterocycle group Chemical group 0.000 description 11
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 239000003480 eluent Substances 0.000 description 10
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 10
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 10
- 238000000746 purification Methods 0.000 description 10
- 125000001424 substituent group Chemical group 0.000 description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- 108091032973 (ribonucleotides)n+m Proteins 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 235000001014 amino acid Nutrition 0.000 description 8
- 210000004027 cell Anatomy 0.000 description 8
- 239000012043 crude product Substances 0.000 description 8
- 238000010511 deprotection reaction Methods 0.000 description 8
- 238000012746 preparative thin layer chromatography Methods 0.000 description 8
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 7
- 125000004430 oxygen atom Chemical group O* 0.000 description 7
- 238000007363 ring formation reaction Methods 0.000 description 7
- 229910052717 sulfur Inorganic materials 0.000 description 7
- 125000004434 sulfur atom Chemical group 0.000 description 7
- PMATZTZNYRCHOR-CGLBZJNRSA-N Cyclosporin A Chemical compound 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 description 6
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- 239000003795 chemical substances by application Substances 0.000 description 6
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- QKFJKGMPGYROCL-UHFFFAOYSA-N phenyl isothiocyanate Chemical compound S=C=NC1=CC=CC=C1 QKFJKGMPGYROCL-UHFFFAOYSA-N 0.000 description 6
- 229920006395 saturated elastomer Polymers 0.000 description 6
- 235000017550 sodium carbonate Nutrition 0.000 description 6
- 229910000029 sodium carbonate Inorganic materials 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 229930105110 Cyclosporin A Natural products 0.000 description 5
- 108010036949 Cyclosporine Proteins 0.000 description 5
- FFBHFFJDDLITSX-UHFFFAOYSA-N benzyl N-[2-hydroxy-4-(3-oxomorpholin-4-yl)phenyl]carbamate Chemical compound OC1=C(NC(=O)OCC2=CC=CC=C2)C=CC(=C1)N1CCOCC1=O FFBHFFJDDLITSX-UHFFFAOYSA-N 0.000 description 5
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- 108091027544 Subgenomic mRNA Proteins 0.000 description 4
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- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 4
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- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- WGRULTCAYDOGQK-UHFFFAOYSA-M sodium;sodium;hydroxide Chemical compound [OH-].[Na].[Na+] WGRULTCAYDOGQK-UHFFFAOYSA-M 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000005888 tetrahydroindolyl group Chemical group 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- PHCBRBWANGJMHS-UHFFFAOYSA-J tetrasodium;disulfate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O PHCBRBWANGJMHS-UHFFFAOYSA-J 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- 125000001984 thiazolidinyl group Chemical group 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- YONPGGFAJWQGJC-UHFFFAOYSA-K titanium(iii) chloride Chemical compound Cl[Ti](Cl)Cl YONPGGFAJWQGJC-UHFFFAOYSA-K 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 210000001644 umbilical artery Anatomy 0.000 description 1
- 210000003954 umbilical cord Anatomy 0.000 description 1
- 210000003606 umbilical vein Anatomy 0.000 description 1
- 210000004291 uterus Anatomy 0.000 description 1
- 210000001215 vagina Anatomy 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 229940100050 virazole Drugs 0.000 description 1
- 238000009736 wetting Methods 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
-
- 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
- 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Virology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Genetics & Genomics (AREA)
- Biophysics (AREA)
- Biochemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US73001105P | 2005-10-26 | 2005-10-26 | |
| US60/730,011 | 2005-10-26 | ||
| US75120405P | 2005-12-19 | 2005-12-19 | |
| US60/751,204 | 2005-12-19 | ||
| PCT/JP2006/321924 WO2007049803A1 (en) | 2005-10-26 | 2006-10-26 | New cyclic peptide compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2623898A1 CA2623898A1 (en) | 2007-05-03 |
| CA2623898C true CA2623898C (en) | 2013-12-24 |
Family
ID=37847219
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2623898A Expired - Fee Related CA2623898C (en) | 2005-10-26 | 2006-10-26 | New cyclic peptide compounds |
Country Status (17)
| Country | Link |
|---|---|
| US (2) | US7872097B2 (https=) |
| EP (1) | EP1957518B1 (https=) |
| JP (1) | JP5218051B2 (https=) |
| KR (1) | KR101273681B1 (https=) |
| CN (1) | CN101305019B (https=) |
| AU (1) | AU2006306974B2 (https=) |
| BR (1) | BRPI0617781A2 (https=) |
| CA (1) | CA2623898C (https=) |
| ES (1) | ES2557477T3 (https=) |
| IL (1) | IL190286A0 (https=) |
| NO (1) | NO20082354L (https=) |
| PL (1) | PL1957518T3 (https=) |
| PT (1) | PT1957518E (https=) |
| RU (1) | RU2423377C2 (https=) |
| TW (1) | TWI391403B (https=) |
| WO (1) | WO2007049803A1 (https=) |
| ZA (1) | ZA200803525B (https=) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2008250254B2 (en) * | 2007-05-02 | 2012-08-16 | Astellas Pharma Inc. | New cyclic peptide compounds |
| JP5625910B2 (ja) * | 2008-09-24 | 2014-11-19 | アステラス製薬株式会社 | ペプチド化合物およびその製造方法 |
| WO2010088573A1 (en) * | 2009-01-30 | 2010-08-05 | Enanta Pharmaceuticals, Inc. | Cyclosporin analogues for preventing or treating hepatitis c infection |
| US8481483B2 (en) | 2009-02-19 | 2013-07-09 | Enanta Pharmaceuticals, Inc. | Cyclosporin analogues |
| AU2010248206A1 (en) * | 2009-05-15 | 2011-12-01 | Stichting Het Nederlands Kanker Instituut | Lysine compounds and their use in site- and chemoselective modification of peptides and proteins |
| US8349312B2 (en) | 2009-07-09 | 2013-01-08 | Enanta Pharmaceuticals, Inc. | Proline substituted cyclosporin analogues |
| US8685917B2 (en) | 2009-07-09 | 2014-04-01 | Enanta Pharmaceuticals, Inc. | Cyclosporin analogues |
| US8367053B2 (en) | 2009-07-09 | 2013-02-05 | Enanta Pharmaceuticals, Inc. | Cyclosporin analogues |
| KR20120125610A (ko) * | 2009-12-30 | 2012-11-16 | 싸이넥시스, 인크. | 시클로스포린 유사체 |
| WO2014035707A1 (en) * | 2012-08-25 | 2014-03-06 | The Johns Hopkins University | Gapdh cascade inhibitor compounds and methods of use and treatment of stress induced disorders including mental illness |
| EP2900684A2 (en) | 2012-09-29 | 2015-08-05 | Novartis AG | Cyclic peptides and use as medicines |
| WO2014085623A1 (en) | 2012-11-28 | 2014-06-05 | Enanta Pharmaceuticals, Inc. | Novel [n-me-4-hydroxyleucine]-9-cyclosporin analogues |
| WO2015031381A1 (en) | 2013-08-26 | 2015-03-05 | Enanta Pharmaceuticals, Inc. | Cyclosporin analogues for preventing or treating hepatitis c |
| US9669095B2 (en) | 2014-11-03 | 2017-06-06 | Enanta Pharmaceuticals, Inc. | Cyclosporin analogues for preventing or treating hepatitis C infection |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH05271267A (ja) * | 1991-04-23 | 1993-10-19 | Fujisawa Pharmaceut Co Ltd | Ｆｒ９０１４５９物質、その製法及び用途 |
| PT1091975E (pt) | 1998-07-01 | 2006-05-31 | Debiopharm Sa | Nova ciclosporina com um perfil de actividade melhorado |
| AR031010A1 (es) | 2000-10-19 | 2003-09-03 | Fujisawa Pharmaceutical Co | Una composicion farmaceutica, util para inhibir el dano celular |
| EP1816138A1 (en) * | 2001-10-19 | 2007-08-08 | Isotechnika,Inc. | Cyclosporine analogue mixtures and their use as immunomodulating agents |
| GB0320638D0 (en) | 2003-09-03 | 2003-10-01 | Novartis Ag | Organic compounds |
| JP2007015926A (ja) * | 2003-10-06 | 2007-01-25 | Fujisawa Pharmaceut Co Ltd | Ｃ型肝炎治療剤 |
| BRPI0515494A (pt) | 2004-10-01 | 2008-07-29 | Debiopharm Sa | uso de [d-meala] 3-[etval] 4-ciclosporina para o tratamento de infecção por hepatite c e composição farmacêutica compreendendo a referida [d-meala] 3-[etval] 4-ciclosporina |
| KR101309409B1 (ko) | 2004-10-01 | 2013-09-23 | 싸이넥시스, 인크. | Ｃ형 간염 바이러스 감염의 치료 및 예방을 위한 ３-에테르및 ３-티오에테르 치환된 시클로스포린 유도체 |
| US7696167B2 (en) | 2004-11-22 | 2010-04-13 | Astellas Pharma Inc. | Cyclic peptide compound |
-
2006
- 2006-10-26 KR KR1020087012431A patent/KR101273681B1/ko not_active Expired - Fee Related
- 2006-10-26 US US12/083,551 patent/US7872097B2/en active Active
- 2006-10-26 PT PT68228444T patent/PT1957518E/pt unknown
- 2006-10-26 BR BRPI0617781-6A patent/BRPI0617781A2/pt not_active Application Discontinuation
- 2006-10-26 TW TW095139941A patent/TWI391403B/zh not_active IP Right Cessation
- 2006-10-26 JP JP2008521463A patent/JP5218051B2/ja not_active Expired - Fee Related
- 2006-10-26 AU AU2006306974A patent/AU2006306974B2/en not_active Ceased
- 2006-10-26 ES ES06822844.4T patent/ES2557477T3/es active Active
- 2006-10-26 PL PL06822844T patent/PL1957518T3/pl unknown
- 2006-10-26 RU RU2008116674/04A patent/RU2423377C2/ru not_active IP Right Cessation
- 2006-10-26 EP EP06822844.4A patent/EP1957518B1/en active Active
- 2006-10-26 CA CA2623898A patent/CA2623898C/en not_active Expired - Fee Related
- 2006-10-26 WO PCT/JP2006/321924 patent/WO2007049803A1/en not_active Ceased
- 2006-10-26 CN CN2006800390294A patent/CN101305019B/zh not_active Expired - Fee Related
-
2008
- 2008-03-19 IL IL190286A patent/IL190286A0/en unknown
- 2008-04-22 ZA ZA2008/03525A patent/ZA200803525B/en unknown
- 2008-05-23 NO NO20082354A patent/NO20082354L/no not_active Application Discontinuation
-
2010
- 2010-07-21 US US12/840,488 patent/US8252895B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CA2623898A1 (en) | 2007-05-03 |
| JP2009513562A (ja) | 2009-04-02 |
| US7872097B2 (en) | 2011-01-18 |
| EP1957518A1 (en) | 2008-08-20 |
| IL190286A0 (en) | 2011-08-01 |
| RU2008116674A (ru) | 2009-10-27 |
| JP5218051B2 (ja) | 2013-06-26 |
| TWI391403B (zh) | 2013-04-01 |
| NO20082354L (no) | 2008-07-01 |
| ES2557477T3 (es) | 2016-01-26 |
| PT1957518E (pt) | 2016-02-26 |
| CN101305019B (zh) | 2012-12-12 |
| BRPI0617781A2 (pt) | 2011-08-09 |
| AU2006306974A1 (en) | 2007-05-03 |
| AU2006306974B2 (en) | 2011-09-22 |
| US20100286033A1 (en) | 2010-11-11 |
| WO2007049803A1 (en) | 2007-05-03 |
| CN101305019A (zh) | 2008-11-12 |
| KR20080065297A (ko) | 2008-07-11 |
| EP1957518B1 (en) | 2015-12-09 |
| US8252895B2 (en) | 2012-08-28 |
| KR101273681B1 (ko) | 2013-06-25 |
| ZA200803525B (en) | 2009-08-26 |
| TW200732351A (en) | 2007-09-01 |
| US20090170755A1 (en) | 2009-07-02 |
| RU2423377C2 (ru) | 2011-07-10 |
| PL1957518T3 (pl) | 2016-07-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20201026 |