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)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Biophysics (AREA)
- Biochemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Genetics & Genomics (AREA)
- Virology (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Communicable Diseases (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Oncology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (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 |
|---|---|---|---|---|
| KR20100017547A (ko) | 2007-05-02 | 2010-02-16 | 아스텔라스세이야쿠 가부시키가이샤 | 신규 시클릭 펩티드 화합물 |
| CN102164947A (zh) * | 2008-09-24 | 2011-08-24 | 安斯泰来制药有限公司 | 肽化合物及其制备方法 |
| KR20110111321A (ko) * | 2009-01-30 | 2011-10-10 | 이난타 파마슈티칼스, 인코포레이티드 | Ｃ형 간염을 예방하거나 치료하기 위한 사이클로스포린 유사체 |
| US8481483B2 (en) | 2009-02-19 | 2013-07-09 | Enanta Pharmaceuticals, Inc. | Cyclosporin analogues |
| SG176085A1 (en) * | 2009-05-15 | 2011-12-29 | Stichting Nl Kanker Inst | 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 |
| US8367053B2 (en) | 2009-07-09 | 2013-02-05 | Enanta Pharmaceuticals, Inc. | Cyclosporin analogues |
| US8685917B2 (en) | 2009-07-09 | 2014-04-01 | Enanta Pharmaceuticals, Inc. | Cyclosporin analogues |
| WO2011082289A1 (en) * | 2009-12-30 | 2011-07-07 | Scynexis Inc. | Cyclosporine analogues |
| JP2015529206A (ja) | 2012-08-25 | 2015-10-05 | ザ・ジョンズ・ホプキンス・ユニバーシティ | Ｇａｐｄｈカスケードインヒビター化合物ならびに使用の方法および精神病を含むストレス誘導障害の処置 |
| 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 |
| JP2016538317A (ja) | 2013-08-26 | 2016-12-08 | エナンタ ファーマシューティカルズ インコーポレイテッド | Ｃ型肝炎を防止または治療するための新規シクロスポリン類似体 |
| 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 |
| AU759480B2 (en) | 1998-07-01 | 2003-04-17 | Debiopharm S.A. | Novel cyclosporin with improved activity profile |
| AU2001295966A1 (en) * | 2000-10-19 | 2002-04-29 | Fujisawa Pharmaceutical Co. Ltd. | Cell damage inhibitor |
| CN100344648C (zh) * | 2001-10-19 | 2007-10-24 | 伊索泰克尼卡股份有限公司 | 环孢菌素类似物混合物及其在制备免疫调节剂中的用途 |
| 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 |
| DK1793844T3 (da) | 2004-10-01 | 2011-03-21 | Debiopharm Sa | Anvendelse af [D-MeAla]3-[EtVal]4-cyklosporin til behandling af hepatitis C-infektion |
| 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 |
| ES2314731T3 (es) * | 2004-11-22 | 2009-03-16 | Astellas Pharma Inc. | Analogo de ciclosporina. |
-
2006
- 2006-10-26 PT PT68228444T patent/PT1957518E/pt unknown
- 2006-10-26 US US12/083,551 patent/US7872097B2/en active Active
- 2006-10-26 TW TW095139941A patent/TWI391403B/zh not_active IP Right Cessation
- 2006-10-26 WO PCT/JP2006/321924 patent/WO2007049803A1/en not_active Ceased
- 2006-10-26 ES ES06822844.4T patent/ES2557477T3/es active Active
- 2006-10-26 BR BRPI0617781-6A patent/BRPI0617781A2/pt not_active Application Discontinuation
- 2006-10-26 PL PL06822844T patent/PL1957518T3/pl unknown
- 2006-10-26 CA CA2623898A patent/CA2623898C/en not_active Expired - Fee Related
- 2006-10-26 KR KR1020087012431A patent/KR101273681B1/ko not_active Expired - Fee Related
- 2006-10-26 AU AU2006306974A patent/AU2006306974B2/en not_active Ceased
- 2006-10-26 JP JP2008521463A patent/JP5218051B2/ja not_active Expired - Fee Related
- 2006-10-26 RU RU2008116674/04A patent/RU2423377C2/ru not_active IP Right Cessation
- 2006-10-26 CN CN2006800390294A patent/CN101305019B/zh not_active Expired - Fee Related
- 2006-10-26 EP EP06822844.4A patent/EP1957518B1/en active Active
-
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 |
|---|---|
| JP2009513562A (ja) | 2009-04-02 |
| US8252895B2 (en) | 2012-08-28 |
| PL1957518T3 (pl) | 2016-07-29 |
| RU2008116674A (ru) | 2009-10-27 |
| CN101305019A (zh) | 2008-11-12 |
| KR101273681B1 (ko) | 2013-06-25 |
| TW200732351A (en) | 2007-09-01 |
| CN101305019B (zh) | 2012-12-12 |
| NO20082354L (no) | 2008-07-01 |
| US7872097B2 (en) | 2011-01-18 |
| IL190286A0 (en) | 2011-08-01 |
| EP1957518A1 (en) | 2008-08-20 |
| RU2423377C2 (ru) | 2011-07-10 |
| ES2557477T3 (es) | 2016-01-26 |
| EP1957518B1 (en) | 2015-12-09 |
| WO2007049803A1 (en) | 2007-05-03 |
| AU2006306974A1 (en) | 2007-05-03 |
| AU2006306974B2 (en) | 2011-09-22 |
| US20100286033A1 (en) | 2010-11-11 |
| US20090170755A1 (en) | 2009-07-02 |
| PT1957518E (pt) | 2016-02-26 |
| CA2623898A1 (en) | 2007-05-03 |
| JP5218051B2 (ja) | 2013-06-26 |
| KR20080065297A (ko) | 2008-07-11 |
| BRPI0617781A2 (pt) | 2011-08-09 |
| ZA200803525B (en) | 2009-08-26 |
| TWI391403B (zh) | 2013-04-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20201026 |