RU2423377C2 - Новые циклические пептидные соединения - Google Patents
Новые циклические пептидные соединения Download PDFInfo
- Publication number
- RU2423377C2 RU2423377C2 RU2008116674/04A RU2008116674A RU2423377C2 RU 2423377 C2 RU2423377 C2 RU 2423377C2 RU 2008116674/04 A RU2008116674/04 A RU 2008116674/04A RU 2008116674 A RU2008116674 A RU 2008116674A RU 2423377 C2 RU2423377 C2 RU 2423377C2
- Authority
- RU
- Russia
- Prior art keywords
- alkyl
- alkoxy
- group
- lower alkyl
- compound
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 201
- 108010069514 Cyclic Peptides Proteins 0.000 title claims abstract description 6
- 102000001189 Cyclic Peptides Human genes 0.000 title claims abstract description 6
- 238000006243 chemical reaction Methods 0.000 claims abstract description 85
- 238000000034 method Methods 0.000 claims abstract description 84
- 150000003839 salts Chemical class 0.000 claims abstract description 65
- 230000000694 effects Effects 0.000 claims abstract description 21
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 9
- 239000003814 drug Substances 0.000 claims abstract description 6
- 238000004519 manufacturing process Methods 0.000 claims description 144
- 125000000217 alkyl group Chemical group 0.000 claims description 93
- 239000000203 mixture Substances 0.000 claims description 80
- -1 amino tert-butoxycarbonyl Chemical group 0.000 claims description 58
- 125000003545 alkoxy group Chemical group 0.000 claims description 53
- 229920006395 saturated elastomer Polymers 0.000 claims description 45
- 229910052739 hydrogen Inorganic materials 0.000 claims description 32
- 239000001257 hydrogen Substances 0.000 claims description 31
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 25
- 125000000623 heterocyclic group Chemical group 0.000 claims description 25
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 23
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 22
- 125000001424 substituent group Chemical group 0.000 claims description 21
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 19
- 208000005176 Hepatitis C Diseases 0.000 claims description 15
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 14
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 9
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000006239 protecting group Chemical group 0.000 claims description 8
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 7
- 239000012634 fragment Substances 0.000 claims description 7
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 230000008707 rearrangement Effects 0.000 claims description 5
- 238000006460 hydrolysis reaction Methods 0.000 claims description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 239000005022 packaging material Substances 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 238000007363 ring formation reaction Methods 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 238000000354 decomposition reaction Methods 0.000 claims description 3
- 238000010511 deprotection reaction Methods 0.000 claims description 3
- 230000002265 prevention Effects 0.000 claims description 3
- 230000001225 therapeutic effect Effects 0.000 claims description 3
- 125000004849 alkoxymethyl group Chemical group 0.000 claims description 2
- 230000003993 interaction Effects 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims 1
- 239000002253 acid Substances 0.000 abstract description 17
- 108091032973 (ribonucleotides)n+m Proteins 0.000 abstract description 9
- 238000002360 preparation method Methods 0.000 abstract description 9
- 239000000126 substance Substances 0.000 abstract description 8
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- 230000002401 inhibitory effect Effects 0.000 abstract description 6
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- 229940079593 drug Drugs 0.000 abstract description 3
- 125000003275 alpha amino acid group Chemical group 0.000 abstract 1
- 230000001747 exhibiting effect Effects 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 132
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 117
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 69
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 55
- 238000001816 cooling Methods 0.000 description 54
- 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
- 239000000843 powder Substances 0.000 description 40
- 239000002904 solvent Substances 0.000 description 38
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 36
- 239000002244 precipitate Substances 0.000 description 35
- 239000011734 sodium Substances 0.000 description 33
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
- 238000003756 stirring Methods 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
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 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
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 16
- 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
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 15
- 239000007787 solid Substances 0.000 description 15
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical class CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 14
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 13
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 13
- 239000012044 organic layer Substances 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-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
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 11
- 239000003480 eluent Substances 0.000 description 10
- 238000000746 purification Methods 0.000 description 10
- 210000004027 cell Anatomy 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- 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 8
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- 238000012746 preparative thin layer chromatography Methods 0.000 description 8
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- 125000004432 carbon atom Chemical group C* 0.000 description 5
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- JQCSUVJDBHJKNG-UHFFFAOYSA-N 1-methoxy-ethyl Chemical group C[CH]OC JQCSUVJDBHJKNG-UHFFFAOYSA-N 0.000 description 4
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- IRPVABHDSJVBNZ-RTHVDDQRSA-N 5-[1-(cyclopropylmethyl)-5-[(1R,5S)-3-(oxetan-3-yl)-3-azabicyclo[3.1.0]hexan-6-yl]pyrazol-3-yl]-3-(trifluoromethyl)pyridin-2-amine Chemical compound C1=C(C(F)(F)F)C(N)=NC=C1C1=NN(CC2CC2)C(C2[C@@H]3CN(C[C@@H]32)C2COC2)=C1 IRPVABHDSJVBNZ-RTHVDDQRSA-N 0.000 description 3
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- SWVGZFQJXVPIKM-UHFFFAOYSA-N n,n-bis(methylamino)propan-1-amine Chemical compound CCCN(NC)NC SWVGZFQJXVPIKM-UHFFFAOYSA-N 0.000 description 3
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- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000000466 oxiranyl group Chemical group 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 229910003445 palladium oxide Inorganic materials 0.000 description 1
- NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 description 1
- JQPTYAILLJKUCY-UHFFFAOYSA-N palladium(ii) oxide Chemical compound [O-2].[Pd+2] JQPTYAILLJKUCY-UHFFFAOYSA-N 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000009984 peri-natal effect Effects 0.000 description 1
- 239000002831 pharmacologic agent Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 210000002826 placenta Anatomy 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000001422 pyrrolinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 238000006462 rearrangement reaction Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000001226 reprecipitation Methods 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
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 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
- 239000003381 stabilizer Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000009747 swallowing Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 229940095064 tartrate Drugs 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
- 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
- UTGPYHWDXYRYGT-UHFFFAOYSA-N tetratriacontanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O UTGPYHWDXYRYGT-UHFFFAOYSA-N 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000001984 thiazolidinyl group Chemical group 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 125000001544 thienyl group Chemical group 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
- VHOCUJPBKOZGJD-UHFFFAOYSA-N triacontanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O VHOCUJPBKOZGJD-UHFFFAOYSA-N 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 210000003454 tympanic membrane Anatomy 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
- JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 0.000 description 1
- 210000000626 ureter Anatomy 0.000 description 1
- 210000004291 uterus Anatomy 0.000 description 1
- 210000001215 vagina Anatomy 0.000 description 1
- 229940100050 virazole Drugs 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 (4)
| 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 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2008116674A RU2008116674A (ru) | 2009-10-27 |
| RU2423377C2 true RU2423377C2 (ru) | 2011-07-10 |
Family
ID=37847219
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2008116674/04A RU2423377C2 (ru) | 2005-10-26 | 2006-10-26 | Новые циклические пептидные соединения |
Country Status (17)
| Country | Link |
|---|---|
| US (2) | US7872097B2 (enExample) |
| EP (1) | EP1957518B1 (enExample) |
| JP (1) | JP5218051B2 (enExample) |
| KR (1) | KR101273681B1 (enExample) |
| CN (1) | CN101305019B (enExample) |
| AU (1) | AU2006306974B2 (enExample) |
| BR (1) | BRPI0617781A2 (enExample) |
| CA (1) | CA2623898C (enExample) |
| ES (1) | ES2557477T3 (enExample) |
| IL (1) | IL190286A0 (enExample) |
| NO (1) | NO20082354L (enExample) |
| PL (1) | PL1957518T3 (enExample) |
| PT (1) | PT1957518E (enExample) |
| RU (1) | RU2423377C2 (enExample) |
| TW (1) | TWI391403B (enExample) |
| WO (1) | WO2007049803A1 (enExample) |
| ZA (1) | ZA200803525B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2492181C2 (ru) * | 2009-01-30 | 2013-09-10 | Энанта Фармасьютикалс, Инк. | Аналоги циклоспорина для предупреждения или лечения инфекции гепатита с |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5459545B2 (ja) * | 2007-05-02 | 2014-04-02 | アステラス製薬株式会社 | 新規環状ペプチド化合物 |
| KR20110073473A (ko) * | 2008-09-24 | 2011-06-29 | 아스텔라스세이야쿠 가부시키가이샤 | 펩티드 화합물 및 그의 제조 방법 |
| 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 |
| EP2519538A1 (en) * | 2009-12-30 | 2012-11-07 | 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 |
| US8906853B2 (en) | 2012-11-28 | 2014-12-09 | Enanta Pharmaceuticals, Inc. | [N-Me-4-hydroxyleucine]-9-cyclosporin analogues for treatment and prevention of hepatitis C infection |
| HK1223843A1 (zh) * | 2013-08-26 | 2017-08-11 | Enanta Pharmaceuticals, Inc. | 用於預防或治療丙型肝炎的環孢菌素類似物 |
| US9669095B2 (en) | 2014-11-03 | 2017-06-06 | Enanta Pharmaceuticals, Inc. | Cyclosporin analogues for preventing or treating hepatitis C infection |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005021028A1 (en) * | 2003-09-03 | 2005-03-10 | Novartis Ag | Use of modified cyclosporins for the treatment of hcv disorders |
| WO2005032576A1 (ja) * | 2003-10-06 | 2005-04-14 | Astellas Pharma Inc. | Ｃ型肝炎治療剤 |
| RU2004110941A (ru) * | 2001-10-19 | 2005-08-10 | Изотехника Инк. (Ca) | Смесь аналогов циклоспорина и ее применение в качестве иммуномодулирующего агента |
Family Cites Families (6)
| 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 |
| JP4350898B2 (ja) | 1998-07-01 | 2009-10-21 | デビオファーム・ソシエテ・アノニム | 活性の特徴が改善された新規のシクロスポリン |
| EP1372695A2 (en) * | 2000-10-19 | 2004-01-02 | Fujisawa Pharmaceutical Co., Ltd. | Cell damage inhibitor |
| EP1793844B1 (en) | 2004-10-01 | 2010-12-08 | Debiopharm S.A. | Use of [d-meala]3-[etval]4-cyclosporin for the treatment of hepatitis c infection |
| 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 RU RU2008116674/04A patent/RU2423377C2/ru not_active IP Right Cessation
- 2006-10-26 AU AU2006306974A patent/AU2006306974B2/en not_active Ceased
- 2006-10-26 BR BRPI0617781-6A patent/BRPI0617781A2/pt not_active Application Discontinuation
- 2006-10-26 PT PT68228444T patent/PT1957518E/pt unknown
- 2006-10-26 CA CA2623898A patent/CA2623898C/en not_active Expired - Fee Related
- 2006-10-26 EP EP06822844.4A patent/EP1957518B1/en active Active
- 2006-10-26 CN CN2006800390294A patent/CN101305019B/zh not_active Expired - Fee Related
- 2006-10-26 US US12/083,551 patent/US7872097B2/en active Active
- 2006-10-26 KR KR1020087012431A patent/KR101273681B1/ko not_active Expired - Fee Related
- 2006-10-26 ES ES06822844.4T patent/ES2557477T3/es active Active
- 2006-10-26 PL PL06822844T patent/PL1957518T3/pl unknown
- 2006-10-26 JP JP2008521463A patent/JP5218051B2/ja not_active Expired - Fee Related
- 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
-
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
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2004110941A (ru) * | 2001-10-19 | 2005-08-10 | Изотехника Инк. (Ca) | Смесь аналогов циклоспорина и ее применение в качестве иммуномодулирующего агента |
| WO2005021028A1 (en) * | 2003-09-03 | 2005-03-10 | Novartis Ag | Use of modified cyclosporins for the treatment of hcv disorders |
| WO2005032576A1 (ja) * | 2003-10-06 | 2005-04-14 | Astellas Pharma Inc. | Ｃ型肝炎治療剤 |
Non-Patent Citations (1)
| Title |
|---|
| Soo Y. Ко*, Roland M. Wenger «Medicinal and biological Chemistry Solid-Phase Total Synthesis of Cyclosporine Analogues», HELVETICA CHIMICA ACTA, 1997, Vol:80, Nr:3, Page(s):695-705. * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2492181C2 (ru) * | 2009-01-30 | 2013-09-10 | Энанта Фармасьютикалс, Инк. | Аналоги циклоспорина для предупреждения или лечения инфекции гепатита с |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1957518B1 (en) | 2015-12-09 |
| US20090170755A1 (en) | 2009-07-02 |
| ES2557477T3 (es) | 2016-01-26 |
| KR20080065297A (ko) | 2008-07-11 |
| AU2006306974A1 (en) | 2007-05-03 |
| TW200732351A (en) | 2007-09-01 |
| CA2623898C (en) | 2013-12-24 |
| PT1957518E (pt) | 2016-02-26 |
| PL1957518T3 (pl) | 2016-07-29 |
| WO2007049803A1 (en) | 2007-05-03 |
| RU2008116674A (ru) | 2009-10-27 |
| EP1957518A1 (en) | 2008-08-20 |
| ZA200803525B (en) | 2009-08-26 |
| BRPI0617781A2 (pt) | 2011-08-09 |
| US7872097B2 (en) | 2011-01-18 |
| TWI391403B (zh) | 2013-04-01 |
| IL190286A0 (en) | 2011-08-01 |
| NO20082354L (no) | 2008-07-01 |
| AU2006306974B2 (en) | 2011-09-22 |
| CN101305019A (zh) | 2008-11-12 |
| KR101273681B1 (ko) | 2013-06-25 |
| CA2623898A1 (en) | 2007-05-03 |
| CN101305019B (zh) | 2012-12-12 |
| JP2009513562A (ja) | 2009-04-02 |
| JP5218051B2 (ja) | 2013-06-26 |
| US8252895B2 (en) | 2012-08-28 |
| US20100286033A1 (en) | 2010-11-11 |
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Legal Events
| Date | Code | Title | Description |
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| MM4A | The patent is invalid due to non-payment of fees |
Effective date: 20191027 |