JP2006526011A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2006526011A5 JP2006526011A5 JP2006509873A JP2006509873A JP2006526011A5 JP 2006526011 A5 JP2006526011 A5 JP 2006526011A5 JP 2006509873 A JP2006509873 A JP 2006509873A JP 2006509873 A JP2006509873 A JP 2006509873A JP 2006526011 A5 JP2006526011 A5 JP 2006526011A5
- Authority
- JP
- Japan
- Prior art keywords
- aliphatic
- optionally
- compound
- cycloalkyl
- aryl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 150000001875 compounds Chemical class 0.000 claims description 82
- 125000006717 (C3-C10) cycloalkenyl group Chemical group 0.000 claims description 57
- 125000001424 substituent group Chemical group 0.000 claims description 52
- 125000001931 aliphatic group Chemical group 0.000 claims description 45
- 125000006714 (C3-C10) heterocyclyl group Chemical group 0.000 claims description 35
- 125000004122 cyclic group Chemical group 0.000 claims description 29
- 125000004429 atoms Chemical group 0.000 claims description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims description 23
- 239000001257 hydrogen Substances 0.000 claims description 23
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 22
- 230000002401 inhibitory effect Effects 0.000 claims description 22
- 239000003112 inhibitor Substances 0.000 claims description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 20
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 19
- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
- 125000001072 heteroaryl group Chemical group 0.000 claims description 17
- 229910052760 oxygen Inorganic materials 0.000 claims description 16
- -1 polymerase Proteins 0.000 claims description 12
- 239000011780 sodium chloride Substances 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 125000005842 heteroatoms Chemical group 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- 239000003443 antiviral agent Substances 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 7
- 125000004433 nitrogen atoms Chemical group N* 0.000 claims description 6
- 102000006992 Interferon-alpha Human genes 0.000 claims description 5
- 108010047761 Interferon-alpha Proteins 0.000 claims description 5
- 102000012479 Serine Proteases Human genes 0.000 claims description 5
- 108010022999 Serine Proteases Proteins 0.000 claims description 5
- 125000004432 carbon atoms Chemical group C* 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 102000033147 ERVK-25 Human genes 0.000 claims description 4
- 108091005771 Peptidases Proteins 0.000 claims description 4
- 239000004365 Protease Substances 0.000 claims description 4
- IWUCXVSUMQZMFG-AFCXAGJDSA-N Ribavirin Chemical group N1=C(C(=O)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 IWUCXVSUMQZMFG-AFCXAGJDSA-N 0.000 claims description 4
- 229960000329 Ribavirin Drugs 0.000 claims description 4
- 239000000969 carrier Substances 0.000 claims description 4
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 101710036216 ATEG_03556 Proteins 0.000 claims description 3
- DKNWSYNQZKUICI-UHFFFAOYSA-N Amantadine Chemical compound C1C(C2)CC3CC2CC1(N)C3 DKNWSYNQZKUICI-UHFFFAOYSA-N 0.000 claims description 3
- 229960003805 Amantadine Drugs 0.000 claims description 3
- 102000003996 Interferon beta Human genes 0.000 claims description 3
- 108090000467 Interferon beta Proteins 0.000 claims description 3
- 102000008070 Interferon-gamma Human genes 0.000 claims description 3
- 108010074328 Interferon-gamma Proteins 0.000 claims description 3
- 101710003000 ORF1/ORF2 Proteins 0.000 claims description 3
- 101700030467 Pol Proteins 0.000 claims description 3
- 102000007501 Thymosin Human genes 0.000 claims description 3
- 108010046075 Thymosin Proteins 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 229940044627 gamma-interferon Drugs 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 239000002955 immunomodulating agent Substances 0.000 claims description 3
- 230000002584 immunomodulator Effects 0.000 claims description 3
- 229940121354 immunomodulators Drugs 0.000 claims description 3
- 101710004466 rgy Proteins 0.000 claims description 3
- 101710030364 rgy1 Proteins 0.000 claims description 3
- 101710030359 rgy2 Proteins 0.000 claims description 3
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 3
- NCDNCNXCDXHOMX-XGKFQTDJSA-N Ritonavir Chemical group N([C@@H](C(C)C)C(=O)N[C@H](C[C@H](O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1SC=NC=1)CC=1C=CC=CC=1)C(=O)N(C)CC1=CSC(C(C)C)=N1 NCDNCNXCDXHOMX-XGKFQTDJSA-N 0.000 claims description 2
- 239000002671 adjuvant Substances 0.000 claims description 2
- 230000000240 adjuvant Effects 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims description 2
- 229960000311 ritonavir Drugs 0.000 claims description 2
- 210000004369 Blood Anatomy 0.000 claims 4
- 210000001124 Body Fluids Anatomy 0.000 claims 4
- 239000008280 blood Substances 0.000 claims 4
- 125000000623 heterocyclic group Chemical group 0.000 claims 4
- 239000012472 biological sample Substances 0.000 claims 3
- 229910052796 boron Inorganic materials 0.000 claims 3
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims 3
- 208000003311 Cytochrome P-450 Enzyme Inhibitors Diseases 0.000 claims 2
- 102000005741 Metalloproteases Human genes 0.000 claims 2
- 108010006035 Metalloproteases Proteins 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 230000002519 immonomodulatory Effects 0.000 claims 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- 239000010839 body fluid Substances 0.000 claims 1
- 238000011109 contamination Methods 0.000 claims 1
- 201000009910 diseases by infectious agent Diseases 0.000 claims 1
- 239000002552 dosage form Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 239000011232 storage material Substances 0.000 claims 1
- 210000001519 tissues Anatomy 0.000 claims 1
- 239000003981 vehicle Substances 0.000 claims 1
- 241000711549 Hepacivirus C Species 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 0 CNC(C(N(C)*)=O)=O Chemical compound CNC(C(N(C)*)=O)=O 0.000 description 5
- 102000014150 Interferons Human genes 0.000 description 5
- 108010050904 Interferons Proteins 0.000 description 5
- 229940079322 interferon Drugs 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 229920000160 (ribonucleotides)n+m Polymers 0.000 description 3
- 208000005176 Hepatitis C Diseases 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- 125000002619 bicyclic group Chemical group 0.000 description 3
- 125000002950 monocyclic group Chemical group 0.000 description 3
- 231100000486 side effect Toxicity 0.000 description 3
- 241000710780 Bovine viral diarrhea virus 1 Species 0.000 description 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N Bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
- 101710034397 IMPDH1 Proteins 0.000 description 2
- WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000012091 fetal bovine serum Substances 0.000 description 2
- 101710004774 gua1 Proteins 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- 101700074809 mpaF Proteins 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 235000019271 petrolatum Nutrition 0.000 description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- 230000000699 topical Effects 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- VDEMEKSASUGYHM-AXDSSHIGSA-N (2S)-3-phenylpyrrolidine-2-carboxylic acid Chemical compound OC(=O)[C@H]1NCCC1C1=CC=CC=C1 VDEMEKSASUGYHM-AXDSSHIGSA-N 0.000 description 1
- BORWTXJNMUOVIN-UHFFFAOYSA-N 1-(4,5-dimethyl-1H-pyrrol-3-yl)ethanone Chemical group CC(=O)C1=CNC(C)=C1C BORWTXJNMUOVIN-UHFFFAOYSA-N 0.000 description 1
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-Bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 1
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-Chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 1
- MYMSJFSOOQERIO-UHFFFAOYSA-N 1-bromodecane Chemical compound CCCCCCCCCCBr MYMSJFSOOQERIO-UHFFFAOYSA-N 0.000 description 1
- PBLNBZIONSLZBU-UHFFFAOYSA-N 1-bromododecane Chemical compound CCCCCCCCCCCCBr PBLNBZIONSLZBU-UHFFFAOYSA-N 0.000 description 1
- WSULSMOGMLRGKU-UHFFFAOYSA-N 1-bromooctadecane Chemical compound CCCCCCCCCCCCCCCCCCBr WSULSMOGMLRGKU-UHFFFAOYSA-N 0.000 description 1
- KOFZTCSTGIWCQG-UHFFFAOYSA-N 1-bromotetradecane Chemical compound CCCCCCCCCCCCCCBr KOFZTCSTGIWCQG-UHFFFAOYSA-N 0.000 description 1
- ZTEHOZMYMCEYRM-UHFFFAOYSA-N 1-chlorodecane Chemical compound CCCCCCCCCCCl ZTEHOZMYMCEYRM-UHFFFAOYSA-N 0.000 description 1
- YAYNEUUHHLGGAH-UHFFFAOYSA-N 1-chlorododecane Chemical compound CCCCCCCCCCCCCl YAYNEUUHHLGGAH-UHFFFAOYSA-N 0.000 description 1
- VUQPJRPDRDVQMN-UHFFFAOYSA-N 1-chlorooctadecane Chemical compound CCCCCCCCCCCCCCCCCCCl VUQPJRPDRDVQMN-UHFFFAOYSA-N 0.000 description 1
- RNHWYOLIEJIAMV-UHFFFAOYSA-N 1-chlorotetradecane Chemical compound CCCCCCCCCCCCCCCl RNHWYOLIEJIAMV-UHFFFAOYSA-N 0.000 description 1
- SKIDNYUZJPMKFC-UHFFFAOYSA-N 1-iododecane Chemical compound CCCCCCCCCCI SKIDNYUZJPMKFC-UHFFFAOYSA-N 0.000 description 1
- GCDPERPXPREHJF-UHFFFAOYSA-N 1-iodododecane Chemical compound CCCCCCCCCCCCI GCDPERPXPREHJF-UHFFFAOYSA-N 0.000 description 1
- ZNJOCVLVYVOUGB-UHFFFAOYSA-N 1-iodooctadecane Chemical compound CCCCCCCCCCCCCCCCCCI ZNJOCVLVYVOUGB-UHFFFAOYSA-N 0.000 description 1
- FHQCFGPKNSSISL-UHFFFAOYSA-N 1-iodotetradecane Chemical compound CCCCCCCCCCCCCCI FHQCFGPKNSSISL-UHFFFAOYSA-N 0.000 description 1
- WMPPDTMATNBGJN-UHFFFAOYSA-N 2-Phenylethylbromide Chemical class BrCCC1=CC=CC=C1 WMPPDTMATNBGJN-UHFFFAOYSA-N 0.000 description 1
- NHHOXAGOCBTLBP-BVKBTSTHSA-N 2-[(1E,3E)-1,5-bis(3,4-dimethyl-1,3-thiazol-3-ium-2-yl)penta-1,3-dien-3-yl]-3,4-dimethyl-1,3-thiazol-3-ium Chemical compound CC1=CSC(C\C=C(/C=C/C2=[N+](C(C)=CS2)C)\C2=[N+](C(C)=CS2)C)=[N+]1C NHHOXAGOCBTLBP-BVKBTSTHSA-N 0.000 description 1
- 229940080296 2-naphthalenesulfonate Drugs 0.000 description 1
- LEACJMVNYZDSKR-UHFFFAOYSA-N 2-octyldodecan-1-ol Chemical compound CCCCCCCCCCC(CO)CCCCCCCC LEACJMVNYZDSKR-UHFFFAOYSA-N 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K 2qpq Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- ZRPLANDPDWYOMZ-UHFFFAOYSA-M 3-cyclopentylpropanoate Chemical compound [O-]C(=O)CCC1CCCC1 ZRPLANDPDWYOMZ-UHFFFAOYSA-M 0.000 description 1
- XMIIGOLPHOKFCH-UHFFFAOYSA-M 3-phenylpropionate Chemical compound [O-]C(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-M 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- 229940009098 Aspartate Drugs 0.000 description 1
- 229940050390 Benzoate Drugs 0.000 description 1
- KMGBZBJJOKUPIA-UHFFFAOYSA-N Butyl iodide Chemical compound CCCCI KMGBZBJJOKUPIA-UHFFFAOYSA-N 0.000 description 1
- LZNHNKWDZCSVFJ-UHFFFAOYSA-N C[N+]1(C2)[IH-]2CCCC1 Chemical compound C[N+]1(C2)[IH-]2CCCC1 LZNHNKWDZCSVFJ-UHFFFAOYSA-N 0.000 description 1
- DSSYKIVIOFKYAU-UHFFFAOYSA-N Camphor Chemical compound C1CC2(C)C(=O)CC1C2(C)C DSSYKIVIOFKYAU-UHFFFAOYSA-N 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N Chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- NEHMKBQYUWJMIP-UHFFFAOYSA-N Chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 1
- 208000006154 Chronic Hepatitis C Diseases 0.000 description 1
- 206010010144 Completed suicide Diseases 0.000 description 1
- 102000002004 Cytochrome P-450 Enzyme System Human genes 0.000 description 1
- 108010015742 Cytochrome P-450 Enzyme System Proteins 0.000 description 1
- YVGGHNCTFXOJCH-UHFFFAOYSA-N DDT Chemical compound C1=CC(Cl)=CC=C1C(C(Cl)(Cl)Cl)C1=CC=C(Cl)C=C1 YVGGHNCTFXOJCH-UHFFFAOYSA-N 0.000 description 1
- CKLJMWTZIZZHCS-UHFFFAOYSA-N DL-aspartic acid Chemical compound OC(=O)C(N)CC(O)=O CKLJMWTZIZZHCS-UHFFFAOYSA-N 0.000 description 1
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical class C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N Diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N Dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N Ethyl iodide Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- AWUCVROLDVIAJX-UHFFFAOYSA-N Glycerol 3-phosphate Chemical compound OCC(O)COP(O)(O)=O AWUCVROLDVIAJX-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 206010019799 Hepatitis viral Diseases 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N Hexanoic acid Chemical class CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- MBBZMMPHUWSWHV-BDVNFPICSA-N Meglumine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
- FEWJPZIEWOKRBE-XIXRPRMCSA-N Mesotartaric acid Chemical compound OC(=O)[C@@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-XIXRPRMCSA-N 0.000 description 1
- 229940050176 Methyl Chloride Drugs 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N Methyl iodide Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 229940042472 Mineral Oil Drugs 0.000 description 1
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N N-Propyl bromide Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 1
- SNMVRZFUUCLYTO-UHFFFAOYSA-N N-Propyl chloride Chemical compound CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 description 1
- PVWOIHVRPOBWPI-UHFFFAOYSA-N N-Propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 1
- WLJNZVDCPSBLRP-UHFFFAOYSA-N Pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
- 229940002988 Pegasys Drugs 0.000 description 1
- 229940106366 Pegintron Drugs 0.000 description 1
- 239000004264 Petrolatum Substances 0.000 description 1
- 229940066842 Petrolatum Drugs 0.000 description 1
- 229950010765 Pivalate Drugs 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N Pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 229920001451 Polypropylene glycol Polymers 0.000 description 1
- 229920001214 Polysorbate 60 Polymers 0.000 description 1
- NIPZZXUFJPQHNH-UHFFFAOYSA-N Pyrazinoic acid Chemical compound OC(=O)C1=CN=CC=N1 NIPZZXUFJPQHNH-UHFFFAOYSA-N 0.000 description 1
- 238000002123 RNA extraction Methods 0.000 description 1
- HVUMOYIDDBPOLL-XWVZOOPGSA-N Sorbitan monostearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O HVUMOYIDDBPOLL-XWVZOOPGSA-N 0.000 description 1
- IJOOHPMOJXWVHK-UHFFFAOYSA-N Trimethylsilyl chloride Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 1
- 208000001756 Virus Disease Diseases 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- LFTYALBVGVNGLI-UHFFFAOYSA-M [Br-].CC([Mg+])=C Chemical compound [Br-].CC([Mg+])=C LFTYALBVGVNGLI-UHFFFAOYSA-M 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 1
- 229940072056 alginate Drugs 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- XEXFVRMLYUDDJY-UHFFFAOYSA-N azane;hydrate;hydrochloride Chemical compound [NH4+].[NH4+].[OH-].[Cl-] XEXFVRMLYUDDJY-UHFFFAOYSA-N 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-M benzoate Chemical compound [O-]C(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-M 0.000 description 1
- 238000006480 benzoylation reaction Methods 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000002527 bicyclic carbocyclic group Chemical group 0.000 description 1
- 238000004166 bioassay Methods 0.000 description 1
- 229940038926 butyl chloride Drugs 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- MIOPJNTWMNEORI-UHFFFAOYSA-M camphorsulfonate anion Chemical compound C1CC2(CS([O-])(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-M 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229920002092 cellular RNA Polymers 0.000 description 1
- 229940081733 cetearyl alcohol Drugs 0.000 description 1
- 230000001684 chronic Effects 0.000 description 1
- 238000002648 combination therapy Methods 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- UWCHSDIUMBNDLT-UHFFFAOYSA-L copper;methylsulfanylmethane;dibromide Chemical compound CSC.Br[Cu]Br UWCHSDIUMBNDLT-UHFFFAOYSA-L 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 125000005356 cycloalkylalkenyl group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000004059 degradation Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 150000008050 dialkyl sulfates Chemical class 0.000 description 1
- LMEDOLJKVASKTP-UHFFFAOYSA-N dibutyl sulfate Chemical compound CCCCOS(=O)(=O)OCCCC LMEDOLJKVASKTP-UHFFFAOYSA-N 0.000 description 1
- 229940008406 diethyl sulfate Drugs 0.000 description 1
- GAFRWLVTHPVQGK-UHFFFAOYSA-N dipentyl sulfate Chemical compound CCCCCOS(=O)(=O)OCCCCC GAFRWLVTHPVQGK-UHFFFAOYSA-N 0.000 description 1
- MOTZDAYCYVMXPC-UHFFFAOYSA-M dodecyl sulfate Chemical compound CCCCCCCCCCCCOS([O-])(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-M 0.000 description 1
- 229940043264 dodecyl sulfate Drugs 0.000 description 1
- 229940079593 drugs Drugs 0.000 description 1
- 241001493065 dsRNA viruses Species 0.000 description 1
- 239000008387 emulsifying waxe Substances 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N fumaric acid Chemical compound OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 1
- UBHWBODXJBSFLH-UHFFFAOYSA-N hexadecan-1-ol;octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO.CCCCCCCCCCCCCCCCCCO UBHWBODXJBSFLH-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- SUMDYPCJJOFFON-UHFFFAOYSA-M isethionate Chemical compound OCCS([O-])(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-M 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M isothiocyanate Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 201000009673 liver disease Diseases 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-L maleate(2-) Chemical compound [O-]C(=O)\C=C/C([O-])=O VZCYOOQTPOCHFL-UPHRSURJSA-L 0.000 description 1
- 239000002609 media Substances 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate Chemical compound CS([O-])(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 229940102396 methyl bromide Drugs 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000006011 modification reaction Methods 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L na2so4 Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- KVBGVZZKJNLNJU-UHFFFAOYSA-M naphthalene-2-sulfonate Chemical compound C1=CC=CC2=CC(S(=O)(=O)[O-])=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-M 0.000 description 1
- PVNIIMVLHYAWGP-UHFFFAOYSA-N nicotinic acid Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 125000006574 non-aromatic ring group Chemical group 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical class [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- 229940075930 picrate Drugs 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 239000001818 polyoxyethylene sorbitan monostearate Substances 0.000 description 1
- 235000010989 polyoxyethylene sorbitan monostearate Nutrition 0.000 description 1
- 229940113124 polysorbate 60 Drugs 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 125000001235 proline group Chemical group [H]N1[C@@](C(=O)[*])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 235000011076 sorbitan monostearate Nutrition 0.000 description 1
- 239000001587 sorbitan monostearate Substances 0.000 description 1
- 229940035048 sorbitan monostearate Drugs 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 230000002142 suicide Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- DCRLSNAODKDTMO-UHFFFAOYSA-N tert-butyl 3-cyclohexylpyrrolidine-2-carboxylate Chemical compound CC(C)(C)OC(=O)C1NCCC1C1CCCCC1 DCRLSNAODKDTMO-UHFFFAOYSA-N 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
- ZDPHROOEEOARMN-UHFFFAOYSA-M undecanoate Chemical compound CCCCCCCCCCC([O-])=O ZDPHROOEEOARMN-UHFFFAOYSA-M 0.000 description 1
- 229960005486 vaccines Drugs 0.000 description 1
- 201000001862 viral hepatitis Diseases 0.000 description 1
- 230000017613 viral reproduction Effects 0.000 description 1
- 230000003612 virological Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000003871 white petrolatum Substances 0.000 description 1
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US10/412,600 US7273885B2 (en) | 2002-04-11 | 2003-04-11 | Inhibitors of serine proteases, particularly HCV NS3-NS4A protease |
US51376503P | 2003-10-23 | 2003-10-23 | |
PCT/US2004/011012 WO2004092162A1 (en) | 2003-04-11 | 2004-04-09 | Inhibitors of serine proteases, particularly hcv ns3-ns4a protease |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2010243570A Division JP2011068655A (ja) | 2003-04-11 | 2010-10-29 | セリンプロテアーゼ(特に、hcvns3−ns4aプロテアーゼ)のインヒビター |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2006526011A JP2006526011A (ja) | 2006-11-16 |
JP2006526011A5 true JP2006526011A5 (US08039623-20111018-C00020.png) | 2007-05-31 |
Family
ID=33302781
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2006509873A Pending JP2006526011A (ja) | 2003-04-11 | 2004-04-09 | セリンプロテアーゼ(特に、hcvns3−ns4aプロテアーゼ)のインヒビター |
JP2010243570A Pending JP2011068655A (ja) | 2003-04-11 | 2010-10-29 | セリンプロテアーゼ(特に、hcvns3−ns4aプロテアーゼ)のインヒビター |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2010243570A Pending JP2011068655A (ja) | 2003-04-11 | 2010-10-29 | セリンプロテアーゼ(特に、hcvns3−ns4aプロテアーゼ)のインヒビター |
Country Status (11)
Families Citing this family (79)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
HU227742B1 (en) | 1996-10-18 | 2012-02-28 | Vertex Pharma | Inhibitors of serine proteases, particularly hepatitis c virus ns3 protease |
DE60111509T2 (de) * | 2000-04-03 | 2006-05-11 | Vertex Pharmaceuticals Inc., Cambridge | Inhibitoren von Serin-Proteasen, insbesondere der Hepatitis-C-Virus NS23-Protease |
SV2003000617A (es) * | 2000-08-31 | 2003-01-13 | Lilly Co Eli | Inhibidores de la proteasa peptidomimetica ref. x-14912m |
TW200403236A (en) * | 2002-04-11 | 2004-03-01 | Vertex Pharma | Inhibitors or serine proteases, particularly HCV NS3-NS4A protease |
EP1613620A1 (en) * | 2003-04-11 | 2006-01-11 | Vertex Pharmaceuticals Incorporated | Inhibitors of serine proteases, particularly hcv ns3-ns4a protease |
PE20050251A1 (es) * | 2003-07-18 | 2005-04-13 | Vertex Pharma | Inhibidores de proteasas serinas, en especial proteasa ns3-ns4a del vhc |
AR045596A1 (es) * | 2003-09-05 | 2005-11-02 | Vertex Pharma | Inhibidores de proteasas de serina en particular proteasa ns3-ns4a del vhc |
CA2538791A1 (en) | 2003-09-18 | 2005-03-31 | Vertex Pharmaceuticals Incorporated | Inhibitors of serine proteases, particularly hcv ns3-ns4a protease |
WO2005037860A2 (en) * | 2003-10-10 | 2005-04-28 | Vertex Pharmaceuticals Incoporated | Inhibitors of serine proteases, particularly hcv ns3-ns4a protease |
EP2311851A3 (en) * | 2004-02-04 | 2011-05-25 | Vertex Pharmaceuticals Incorporated | Inhibitors of serine proteases, particularly HCV NS3-NS4A protease |
NZ563909A (en) | 2005-05-13 | 2011-10-28 | Virochem Pharma Inc | Thiophene derivatives and their use for the treatment or prevention of flavivirus infections |
AU2006275413B2 (en) * | 2005-08-02 | 2012-07-19 | Vertex Pharmaceuticals Incorporated | Inhibitors of serine proteases |
US8399615B2 (en) | 2005-08-19 | 2013-03-19 | Vertex Pharmaceuticals Incorporated | Processes and intermediates |
AR055395A1 (es) | 2005-08-26 | 2007-08-22 | Vertex Pharma | Compuestos inhibidores de la actividad de la serina proteasa ns3-ns4a del virus de la hepatitis c |
US7964624B1 (en) | 2005-08-26 | 2011-06-21 | Vertex Pharmaceuticals Incorporated | Inhibitors of serine proteases |
US7705138B2 (en) | 2005-11-11 | 2010-04-27 | Vertex Pharmaceuticals Incorporated | Hepatitis C virus variants |
KR20140098867A (ko) | 2005-11-11 | 2014-08-08 | 버텍스 파마슈티칼스 인코포레이티드 | C형 간염 바이러스 변이체 |
US7456165B2 (en) * | 2006-02-08 | 2008-11-25 | Bristol-Myers Squibb Company | HCV NS5B inhibitors |
WO2007098270A2 (en) | 2006-02-27 | 2007-08-30 | Vertex Pharmaceuticals Incorporated | Co-crystals comprising vx-950 and pharmaceutical compositions comprising the same |
BRPI0709567A2 (pt) * | 2006-03-16 | 2011-07-12 | Vertex Pharma | inibidores deuterados de protease de hepatite c |
MX2008012225A (es) * | 2006-03-23 | 2008-12-03 | Schering Corp | Combinaciones de inhibidores de proteasa de virus de hepatitis c e inhibidores de isoenzima 3a4 del citocromo p450, y metodos de tratamiento relacionados con las mismas. |
MX2009005185A (es) | 2006-11-15 | 2009-07-07 | Virochem Pharma Inc | Analogos de tiofeno para el tratamiento o prevencion de infecciones de flavivirus. |
AP2009004960A0 (en) * | 2007-02-27 | 2009-08-31 | Vertex Pharma | Co-crystals and pharmaceutical compositions comprising the same |
NZ579295A (en) * | 2007-02-27 | 2012-03-30 | Vertex Pharma | Inhibitors of serine proteases |
WO2009003009A1 (en) * | 2007-06-26 | 2008-12-31 | Enanta Pharmaceuticals, Inc. | Substituted pyrrolidine as anti-infectives |
US20090022689A1 (en) * | 2007-07-18 | 2009-01-22 | Yat Sun Or | C4-spiro-pyrrolidine antivirals |
US8492546B2 (en) | 2007-08-30 | 2013-07-23 | Vertex Pharmaceuticals Incorporated | Co-crystals and pharmaceutical compositions comprising the same |
US20090060874A1 (en) * | 2007-09-05 | 2009-03-05 | Yao-Ling Qiu | Bicyclic pyrrolidine derivatives |
NZ587133A (en) * | 2008-02-04 | 2012-10-26 | Idenix Pharmaceuticals Inc | Macrocyclic serine protease inhibitor compounds for treating an HCV infection |
US20090233972A1 (en) * | 2008-03-12 | 2009-09-17 | Yat Sun Or | Substituted heterocycles as anti-infectives |
US20090324544A1 (en) * | 2008-06-11 | 2009-12-31 | Yao-Ling Qiu | Substituted cyclic pyrrolidine derivatives |
US20090326019A1 (en) * | 2008-06-11 | 2009-12-31 | Yat Sun Or | 3,4-bicyclic pyrrolidine antivirals |
US20100074863A1 (en) * | 2008-09-17 | 2010-03-25 | Yat Sun Or | Anti-infective pyrrolidine derivatives and analogs |
US8102720B2 (en) * | 2009-02-02 | 2012-01-24 | Qualcomm Incorporated | System and method of pulse generation |
JP5690286B2 (ja) | 2009-03-04 | 2015-03-25 | イデニク プハルマセウティカルス,インコーポレイテッド | ホスホチオフェン及びホスホチアゾールhcvポリメラーゼ阻害剤 |
CA2758072A1 (en) | 2009-04-08 | 2010-10-14 | Idenix Pharmaceuticals, Inc. | Macrocyclic serine protease inhibitors |
US8980920B2 (en) | 2009-05-29 | 2015-03-17 | Merck Sharp & Dohme Corp. | Antiviral compounds of three linked aryl moieties to treat diseases such as hepatitis C |
WO2011017389A1 (en) | 2009-08-05 | 2011-02-10 | Idenix Pharmaceuticals, Inc. | Macrocyclic serine protease inhibitors useful against viral infections, particularly hcv |
HUE030402T2 (en) | 2009-09-15 | 2017-05-29 | Taigen Biotechnology Co Ltd | HCV protease inhibitors |
WO2011063076A1 (en) | 2009-11-19 | 2011-05-26 | Itherx Pharmaceuticals, Inc. | Methods of treating hepatitis c virus with oxoacetamide compounds |
WO2011068715A1 (en) | 2009-11-25 | 2011-06-09 | Vertex Pharmaceuticals Incorporated | 5-alkynyl-thiophene-2-carboxylic acid derivatives and their use for the treatment or prevention of flavivirus infections |
WO2011066241A1 (en) | 2009-11-25 | 2011-06-03 | Schering Corporation | Fused tricyclic compounds and derivatives thereof useful for the treatment of viral diseases |
JP2013514982A (ja) | 2009-12-18 | 2013-05-02 | イデニク プハルマセウティカルス,インコーポレイテッド | 5,5−縮合アリーレン又はヘテロアリーレンc型肝炎ウイルス阻害剤 |
WO2011087740A1 (en) | 2009-12-22 | 2011-07-21 | Schering Corporation | Fused tricyclic compounds and methods of use thereof for the treatment of viral diseases |
US20130072523A1 (en) | 2009-12-24 | 2013-03-21 | Vertex Pharmaceuticals Incorporated | Analogues for the treatment or prevention of flavivirus infections |
US8609635B2 (en) | 2010-03-09 | 2013-12-17 | Merck Sharp & Dohme Corp. | Fused tricyclic silyl compounds and methods of use thereof for the treatment of viral diseases |
TW201141857A (en) | 2010-03-24 | 2011-12-01 | Vertex Pharma | Analogues for the treatment or prevention of flavivirus infections |
CN103038237A (zh) | 2010-03-24 | 2013-04-10 | 沃泰克斯药物股份有限公司 | 用于黄病毒感染治疗或预防的类似物 |
WO2011119858A1 (en) | 2010-03-24 | 2011-09-29 | Vertex Pharmaceuticals Incorporated | Analogues for the treatment or prevention of flavivirus infections |
WO2011119853A1 (en) | 2010-03-24 | 2011-09-29 | Vertex Pharmaceuticals Incorporated | Analogues for the treatment or prevention of flavivirus infections |
WO2011156545A1 (en) | 2010-06-09 | 2011-12-15 | Vertex Pharmaceuticals Incorporated | Viral dynamic model for hcv combination therapy |
US20130157258A1 (en) | 2010-06-15 | 2013-06-20 | Vertex Pharmaceuticals Incorporated | Hcv ns5b protease mutants |
MX2012014918A (es) | 2010-06-28 | 2013-04-08 | Vertex Pharma | Compuestos y metodos para tratamiento o prevencion de infecciones por flavivirus. |
JP2013531011A (ja) | 2010-06-28 | 2013-08-01 | バーテックス ファーマシューティカルズ インコーポレイテッド | フラビウイルス感染の処置または予防のための化合物および方法 |
WO2012006070A1 (en) | 2010-06-28 | 2012-01-12 | Vertex Pharmaceuticals Incorporated | Compounds and methods for the treatment or prevention of flavivirus infections |
EP2598149A4 (en) | 2010-07-26 | 2014-09-10 | Merck Sharp & Dohme | SUBSTITUTED BIPHENYLENE COMPOUNDS AND METHOD FOR USE THEREOF FOR THE TREATMENT OF VIRUS DISEASES |
CN103153978A (zh) | 2010-08-17 | 2013-06-12 | 沃泰克斯药物股份有限公司 | 用于治疗或预防黄病毒科病毒感染的化合物和方法 |
AU2011314168A1 (en) | 2010-09-29 | 2013-04-04 | Merck Sharp & Dohme Corp. | Fused tetracycle derivatives and methods of use thereof for the treatment of viral diseases |
US9353100B2 (en) | 2011-02-10 | 2016-05-31 | Idenix Pharmaceuticals Llc | Macrocyclic serine protease inhibitors, pharmaceutical compositions thereof, and their use for treating HCV infections |
US20120252721A1 (en) | 2011-03-31 | 2012-10-04 | Idenix Pharmaceuticals, Inc. | Methods for treating drug-resistant hepatitis c virus infection with a 5,5-fused arylene or heteroarylene hepatitis c virus inhibitor |
US9061041B2 (en) | 2011-04-13 | 2015-06-23 | Merck Sharp & Dohme Corp. | 2′-substituted nucleoside derivatives and methods of use thereof for the treatment of viral diseases |
US9156872B2 (en) | 2011-04-13 | 2015-10-13 | Merck Sharp & Dohme Corp. | 2′-azido substituted nucleoside derivatives and methods of use thereof for the treatment of viral diseases |
WO2013016499A1 (en) | 2011-07-26 | 2013-01-31 | Vertex Pharmaceuticals Incorporated | Methods for preparation of thiophene compounds |
AR087344A1 (es) | 2011-07-26 | 2014-03-19 | Vertex Pharma | Formas polimorficas del acido 5-(3,3-dimetil-but-1-inil)-3-[(trans-4-hidroxi-ciclohexil)-(trans-4-metil-ciclohexancarbonil)-amino]-tiofen-2-carboxilico y su uso en el tratamiento de la hepatitis c |
WO2013033901A1 (en) | 2011-09-08 | 2013-03-14 | Merck Sharp & Dohme Corp. | Heterocyclic-substituted benzofuran derivatives and methods of use thereof for the treatment of viral diseases |
WO2013033900A1 (en) | 2011-09-08 | 2013-03-14 | Merck Sharp & Dohme Corp. | Tetracyclic heterocycle compounds and methods of use thereof for the treatment of viral diseases |
WO2013033899A1 (en) | 2011-09-08 | 2013-03-14 | Merck Sharp & Dohme Corp. | Substituted benzofuran compounds and methods of use thereof for the treatment of viral diseases |
US20140378416A1 (en) | 2011-09-14 | 2014-12-25 | Michael P. Dwyer | Silyl-containing heterocyclic compounds and methods of use thereof for the treatment of viral diseases |
US20130123276A1 (en) | 2011-11-14 | 2013-05-16 | Sven Ruf | Use of telaprevir and related compounds in atherosclerosis, heart failure, renal diseases, liver diseases or inflammatory diseases |
NZ630805A (en) | 2012-03-22 | 2016-01-29 | Alios Biopharma Inc | Pharmaceutical combinations comprising a thionucleotide analog |
KR102161077B1 (ko) * | 2012-06-29 | 2020-09-29 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | 반도체 장치 |
WO2014053533A1 (en) | 2012-10-05 | 2014-04-10 | Sanofi | Use of substituted 3-heteroaroylamino-propionic acid derivatives as pharmaceuticals for prevention/treatment of atrial fibrillation |
US20150065439A1 (en) | 2013-02-28 | 2015-03-05 | Vertex Pharmaceuticals Incorporated | Pharmaceutical compositions |
US20160229866A1 (en) | 2013-09-20 | 2016-08-11 | Idenix Pharmaceuticals Inc. | Hepatitis c virus inhibitors |
EP3063140A4 (en) | 2013-10-30 | 2017-11-08 | Merck Sharp & Dohme Corp. | Pseudopolymorphs of an hcv ns5a inhibitor and uses thereof |
US20170066779A1 (en) | 2014-03-05 | 2017-03-09 | Idenix Pharmaceuticals Llc | Solid forms of a flaviviridae virus inhibitor compound and salts thereof |
WO2015134561A1 (en) | 2014-03-05 | 2015-09-11 | Idenix Pharmaceuticals, Inc. | Pharmaceutical compositions comprising a 5,5-fused heteroarylene flaviviridae inhibitor and their use for treating or preventing flaviviridae infection |
BR112018076614A2 (pt) | 2016-06-21 | 2019-04-02 | Orion Ophthalmology LLC | derivados heterocíclicos de prolinamida |
EP3472151A4 (en) | 2016-06-21 | 2020-03-04 | Orion Ophthalmology LLC | CARBOCYCLIC PROLINAMIDE DERIVATIVES |
Family Cites Families (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US534410A (en) * | 1895-02-19 | Sylvania | ||
US4499082A (en) * | 1983-12-05 | 1985-02-12 | E. I. Du Pont De Nemours And Company | α-Aminoboronic acid peptides |
NZ235155A (en) * | 1989-09-11 | 1993-04-28 | Merrell Dow Pharma | Peptidase substrates in which the carboxy terminal group has been replaced by a tricarbonyl radical |
WO1992012140A1 (en) * | 1990-12-28 | 1992-07-23 | Georgia Tech Research Corporation | Peptides ketoamides, ketoacids, and ketoesters |
US5384410A (en) | 1993-03-24 | 1995-01-24 | The Du Pont Merck Pharmaceutical Company | Removal of boronic acid protecting groups by transesterification |
US5807876A (en) | 1996-04-23 | 1998-09-15 | Vertex Pharmaceuticals Incorporated | Inhibitors of IMPDH enzyme |
HU227742B1 (en) * | 1996-10-18 | 2012-02-28 | Vertex Pharma | Inhibitors of serine proteases, particularly hepatitis c virus ns3 protease |
GB9623908D0 (en) * | 1996-11-18 | 1997-01-08 | Hoffmann La Roche | Amino acid derivatives |
GB9707659D0 (en) * | 1997-04-16 | 1997-06-04 | Peptide Therapeutics Ltd | Hepatitis C NS3 Protease inhibitors |
EP1066247B1 (en) * | 1998-03-31 | 2006-11-22 | Vertex Pharmaceuticals Incorporated | Inhibitors of serine proteases, particularly hepatitis c virus ns3 protease |
CZ301802B6 (cs) | 1999-03-19 | 2010-06-30 | Vertex Pharmaceuticals Incorporated | Deriváty mocoviny jako inhibitory IMPDH a farmaceutické prostredky s jejich obsahem |
WO2001002601A2 (en) * | 1999-07-07 | 2001-01-11 | Du Pont Pharmaceuticals Company | Cell-based assay systems for examining hcv ns3 protease activity |
EP1252178A1 (en) * | 1999-12-03 | 2002-10-30 | Bristol-Myers Squibb Pharma Company | Alpha-ketoamide inhibitors of hepatitis c virus ns3 protease |
DE60111509T2 (de) * | 2000-04-03 | 2006-05-11 | Vertex Pharmaceuticals Inc., Cambridge | Inhibitoren von Serin-Proteasen, insbesondere der Hepatitis-C-Virus NS23-Protease |
WO2002008251A2 (en) * | 2000-07-21 | 2002-01-31 | Corvas International, Inc. | Peptides as ns3-serine protease inhibitors of hepatitis c virus |
AR029851A1 (es) * | 2000-07-21 | 2003-07-16 | Dendreon Corp | Nuevos peptidos como inhibidores de ns3-serina proteasa del virus de hepatitis c |
RU2355700C9 (ru) * | 2000-07-21 | 2010-03-20 | Шеринг Корпорейшн | Новые пептиды как ингибиторы ns3-серинпротеазы вируса гепатита с |
SV2003000617A (es) * | 2000-08-31 | 2003-01-13 | Lilly Co Eli | Inhibidores de la proteasa peptidomimetica ref. x-14912m |
TW200403236A (en) | 2002-04-11 | 2004-03-01 | Vertex Pharma | Inhibitors or serine proteases, particularly HCV NS3-NS4A protease |
-
2004
- 2004-04-09 CN CNB2004800140478A patent/CN100453553C/zh not_active Expired - Fee Related
- 2004-04-09 WO PCT/US2004/011012 patent/WO2004092162A1/en active Application Filing
- 2004-04-09 ES ES04759362T patent/ES2381548T3/es not_active Expired - Lifetime
- 2004-04-09 EP EP10178023A patent/EP2332935A1/en not_active Withdrawn
- 2004-04-09 CA CA002521678A patent/CA2521678A1/en not_active Abandoned
- 2004-04-09 AU AU2004230946A patent/AU2004230946A1/en not_active Abandoned
- 2004-04-09 AT AT04759362T patent/ATE547412T1/de active
- 2004-04-09 EP EP04759362A patent/EP1636208B1/en not_active Expired - Lifetime
- 2004-04-09 JP JP2006509873A patent/JP2006526011A/ja active Pending
- 2004-04-09 US US10/821,793 patent/US20050090450A1/en not_active Abandoned
- 2004-04-12 AR ARP040101227A patent/AR044513A1/es unknown
-
2006
- 2006-10-18 HK HK06111435.4A patent/HK1090644A1/xx not_active IP Right Cessation
-
2008
- 2008-07-08 US US12/169,209 patent/US20090022688A1/en not_active Abandoned
-
2010
- 2010-10-29 JP JP2010243570A patent/JP2011068655A/ja active Pending
-
2011
- 2011-09-21 US US13/238,386 patent/US8618152B2/en not_active Expired - Fee Related
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP2006526011A5 (US08039623-20111018-C00020.png) | ||
JP4745230B2 (ja) | セリンプロテアーゼ、特に、hcvns3−ns4aプロテアーゼの阻害剤 | |
JP4806154B2 (ja) | セリンプロテアーゼ、特にc型肝炎ウイルスns3プロテアーゼのインヒビター | |
RU2441020C2 (ru) | Ингибиторы серинпротеазы | |
JP4767852B2 (ja) | セリンプロテアーゼ、特にhcvns3‐ns4aの阻害剤 | |
JP4685775B2 (ja) | セリンプロテアーゼ、とりわけhcvns3−ns4aプロテアーゼの阻害剤 | |
CN1938332B (zh) | 丝氨酸蛋白酶、特别是hcv ns3-ns4a蛋白酶的抑制剂 | |
US7273885B2 (en) | Inhibitors of serine proteases, particularly HCV NS3-NS4A protease | |
JP2011068655A (ja) | セリンプロテアーゼ(特に、hcvns3−ns4aプロテアーゼ)のインヒビター | |
CN101857631A (zh) | 丝氨酸蛋白酶、特别是hcv ns3-ns4a蛋白酶的抑制剂 | |
CN108349945A (zh) | Hcv抑制剂、其制备方法与应用 | |
CN1906208B (zh) | 丝氨酸蛋白酶、特别是hcv ns3-ns4a蛋白酶的抑制剂 | |
TW200427684A (en) | Inhibitors of serine proteases, particularly HCV ns3-ns4a protease |