MX2013012870A - Inhibidores del virus de la hepatitis c. - Google Patents
Inhibidores del virus de la hepatitis c.Info
- Publication number
- MX2013012870A MX2013012870A MX2013012870A MX2013012870A MX2013012870A MX 2013012870 A MX2013012870 A MX 2013012870A MX 2013012870 A MX2013012870 A MX 2013012870A MX 2013012870 A MX2013012870 A MX 2013012870A MX 2013012870 A MX2013012870 A MX 2013012870A
- Authority
- MX
- Mexico
- Prior art keywords
- diyl
- alkyl
- mmol
- cap
- oxo
- Prior art date
Links
- 239000003112 inhibitor Substances 0.000 title claims description 3
- 241000711549 Hepacivirus C Species 0.000 title abstract description 55
- 239000000203 mixture Substances 0.000 claims abstract description 213
- 150000001875 compounds Chemical class 0.000 claims abstract description 127
- 208000015181 infectious disease Diseases 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 165
- -1 hexane-3, 2-diyl Chemical group 0.000 claims description 140
- 229910052739 hydrogen Inorganic materials 0.000 claims description 109
- 125000003118 aryl group Chemical group 0.000 claims description 67
- 125000000623 heterocyclic group Chemical group 0.000 claims description 58
- 125000005843 halogen group Chemical group 0.000 claims description 54
- 150000003839 salts Chemical class 0.000 claims description 53
- 229910052757 nitrogen Inorganic materials 0.000 claims description 52
- 239000001257 hydrogen Substances 0.000 claims description 44
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 43
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 37
- 125000001188 haloalkyl group Chemical group 0.000 claims description 36
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 34
- 125000003545 alkoxy group Chemical group 0.000 claims description 30
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 29
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 26
- 229910052799 carbon Inorganic materials 0.000 claims description 24
- 150000001602 bicycloalkyls Chemical group 0.000 claims description 22
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 22
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 20
- 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 claims description 20
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 20
- 150000001721 carbon Chemical group 0.000 claims description 18
- 229920006395 saturated elastomer Polymers 0.000 claims description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 17
- 125000001424 substituent group Chemical group 0.000 claims description 17
- 108010050904 Interferons Proteins 0.000 claims description 16
- 102000014150 Interferons Human genes 0.000 claims description 16
- 125000005099 aryl alkyl carbonyl group Chemical group 0.000 claims description 16
- 125000006517 heterocyclyl carbonyl group Chemical group 0.000 claims description 16
- 229940079322 interferon Drugs 0.000 claims description 16
- 101800001014 Non-structural protein 5A Proteins 0.000 claims description 15
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 15
- 230000000694 effects Effects 0.000 claims description 15
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 13
- 229910052717 sulfur Inorganic materials 0.000 claims description 13
- RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical compound C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 12
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 12
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 11
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 11
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 11
- 108010047761 Interferon-alpha Proteins 0.000 claims description 9
- 102000006992 Interferon-alpha Human genes 0.000 claims description 9
- IWUCXVSUMQZMFG-AFCXAGJDSA-N Ribavirin Chemical compound 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 9
- 239000003937 drug carrier Substances 0.000 claims description 9
- 229960000329 ribavirin Drugs 0.000 claims description 9
- HZCAHMRRMINHDJ-DBRKOABJSA-N ribavirin Natural products O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1N=CN=C1 HZCAHMRRMINHDJ-DBRKOABJSA-N 0.000 claims description 9
- 229910003827 NRaRb Inorganic materials 0.000 claims description 8
- 125000004702 alkoxy alkyl carbonyl group Chemical group 0.000 claims description 7
- 125000004122 cyclic group Chemical group 0.000 claims description 7
- 108091032973 (ribonucleotides)n+m Proteins 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- 108060004795 Methyltransferase Proteins 0.000 claims description 6
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 6
- 125000005170 cycloalkyloxycarbonyl group Chemical group 0.000 claims description 6
- 125000005144 cycloalkylsulfonyl group Chemical group 0.000 claims description 6
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 6
- 125000004993 haloalkoxycarbonyl group Chemical group 0.000 claims description 6
- 125000005182 hydroxyalkylcarbonyl group Chemical group 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 108010006035 Metalloproteases Proteins 0.000 claims description 5
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- 101800001019 Non-structural protein 4B Proteins 0.000 claims description 5
- 108010022999 Serine Proteases Proteins 0.000 claims description 5
- 102000012479 Serine Proteases Human genes 0.000 claims description 5
- 125000005092 alkenyloxycarbonyl group Chemical group 0.000 claims description 5
- 238000011161 development Methods 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 229910052702 rhenium Inorganic materials 0.000 claims description 5
- 125000004001 thioalkyl group Chemical group 0.000 claims description 5
- UBCHPRBFMUDMNC-UHFFFAOYSA-N 1-(1-adamantyl)ethanamine Chemical compound C1C(C2)CC3CC2CC1(C(N)C)C3 UBCHPRBFMUDMNC-UHFFFAOYSA-N 0.000 claims description 4
- 108020005544 Antisense RNA Proteins 0.000 claims description 4
- 101710200424 Inosine-5'-monophosphate dehydrogenase Proteins 0.000 claims description 4
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- 108010079944 Interferon-alpha2b Proteins 0.000 claims description 4
- 102000013462 Interleukin-12 Human genes 0.000 claims description 4
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- 102000000588 Interleukin-2 Human genes 0.000 claims description 4
- 108010002350 Interleukin-2 Proteins 0.000 claims description 4
- 230000005867 T cell response Effects 0.000 claims description 4
- DKNWSYNQZKUICI-UHFFFAOYSA-N amantadine Chemical compound C1C(C2)CC3CC2CC1(N)C3 DKNWSYNQZKUICI-UHFFFAOYSA-N 0.000 claims description 4
- 229960003805 amantadine Drugs 0.000 claims description 4
- 239000003184 complementary RNA Substances 0.000 claims description 4
- 210000002443 helper t lymphocyte Anatomy 0.000 claims description 4
- 229960002751 imiquimod Drugs 0.000 claims description 4
- DOUYETYNHWVLEO-UHFFFAOYSA-N imiquimod Chemical compound C1=CC=CC2=C3N(CC(C)C)C=NC3=C(N)N=C21 DOUYETYNHWVLEO-UHFFFAOYSA-N 0.000 claims description 4
- 230000002452 interceptive effect Effects 0.000 claims description 4
- 229940117681 interleukin-12 Drugs 0.000 claims description 4
- GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 claims description 4
- 229960000888 rimantadine Drugs 0.000 claims description 4
- 229910052701 rubidium Inorganic materials 0.000 claims description 4
- 102000004889 Interleukin-6 Human genes 0.000 claims description 3
- 108090001005 Interleukin-6 Proteins 0.000 claims description 3
- 125000002837 carbocyclic group Chemical group 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 125000002883 imidazolyl group Chemical group 0.000 claims description 3
- 108700027921 interferon tau Proteins 0.000 claims description 3
- 229940100601 interleukin-6 Drugs 0.000 claims description 3
- 229930010555 Inosine Natural products 0.000 claims description 2
- UGQMRVRMYYASKQ-KQYNXXCUSA-N Inosine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C2=NC=NC(O)=C2N=C1 UGQMRVRMYYASKQ-KQYNXXCUSA-N 0.000 claims description 2
- 239000002348 inosinate dehydrogenase inhibitor Substances 0.000 claims description 2
- 229960003786 inosine Drugs 0.000 claims description 2
- PQJFJRGZSZKPTF-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O.COC(N)=O PQJFJRGZSZKPTF-UHFFFAOYSA-N 0.000 claims 28
- NXFFJDQHYLNEJK-UHFFFAOYSA-N 2-[4-[(4-chlorophenyl)methyl]-7-fluoro-5-methylsulfonyl-2,3-dihydro-1h-cyclopenta[b]indol-3-yl]acetic acid Chemical compound C1=2C(S(=O)(=O)C)=CC(F)=CC=2C=2CCC(CC(O)=O)C=2N1CC1=CC=C(Cl)C=C1 NXFFJDQHYLNEJK-UHFFFAOYSA-N 0.000 claims 8
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims 4
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 3
- 125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 claims 3
- 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- 101710088194 Dehydrogenase Proteins 0.000 claims 1
- 102100026459 POU domain, class 3, transcription factor 2 Human genes 0.000 claims 1
- 101710133394 POU domain, class 3, transcription factor 2 Proteins 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 40
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- 239000002904 solvent Substances 0.000 description 128
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- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 88
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 65
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- 235000019198 oils Nutrition 0.000 description 62
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 59
- 101150041968 CDC13 gene Proteins 0.000 description 55
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 46
- 230000014759 maintenance of location Effects 0.000 description 39
- 239000011734 sodium Substances 0.000 description 37
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 35
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 34
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- GNFTZDOKVXKIBK-UHFFFAOYSA-N 3-(2-methoxyethoxy)benzohydrazide Chemical compound COCCOC1=CC=CC(C(=O)NN)=C1 GNFTZDOKVXKIBK-UHFFFAOYSA-N 0.000 description 22
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- YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 5
- 125000004043 oxo group Chemical group O=* 0.000 description 5
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- YSHDPXQDVKNPKA-UHFFFAOYSA-N tert-butyl 2-(benzhydrylideneamino)acetate Chemical compound C=1C=CC=CC=1C(=NCC(=O)OC(C)(C)C)C1=CC=CC=C1 YSHDPXQDVKNPKA-UHFFFAOYSA-N 0.000 description 1
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- PQDJYEQOELDLCP-UHFFFAOYSA-N trimethylsilane Chemical compound C[SiH](C)C PQDJYEQOELDLCP-UHFFFAOYSA-N 0.000 description 1
- XHVSCKNABCCCAC-UHFFFAOYSA-N trimethylsilyl 2,2-difluoro-2-fluorosulfonylacetate Chemical compound C[Si](C)(C)OC(=O)C(F)(F)S(F)(=O)=O XHVSCKNABCCCAC-UHFFFAOYSA-N 0.000 description 1
- LEIMLDGFXIOXMT-UHFFFAOYSA-N trimethylsilyl cyanide Chemical compound C[Si](C)(C)C#N LEIMLDGFXIOXMT-UHFFFAOYSA-N 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A61K31/4178—1,3-Diazoles not condensed 1,3-diazoles and containing further heterocyclic rings, e.g. pilocarpine, nitrofurantoin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A61K31/4184—1,3-Diazoles condensed with carbocyclic rings, e.g. benzimidazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Virology (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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| EP2714693A4 (en) | 2011-05-26 | 2014-12-10 | Abbvie Inc | ANTIVIRAL COMPOUNDS |
| EP2714035A4 (en) | 2011-05-26 | 2014-11-05 | Abbvie Inc | ANTIVIRAL CONNECTIONS |
| PH12013502455A1 (en) | 2011-05-27 | 2014-01-20 | Achillion Pharmaceuticals Inc | Substituted aliphanes, cyclophanes, heteraphanes, heterophanes, hetero-heteraphanes and metallocenes useful for treating hcv infections |
| WO2012175581A1 (en) | 2011-06-24 | 2012-12-27 | F. Hoffmann-La Roche Ag | Antiviral compounds |
| EP2730572B1 (en) | 2011-07-09 | 2015-09-16 | Sunshine Lake Pharma Co., Ltd. | Spiro compounds as hepatitis c virus inhibitors |
-
2012
- 2012-05-07 US US13/465,298 patent/US9546160B2/en active Active
- 2012-05-09 MX MX2013012870A patent/MX2013012870A/es unknown
- 2012-05-09 AU AU2012253578A patent/AU2012253578A1/en not_active Abandoned
- 2012-05-09 KR KR1020137032604A patent/KR20140037114A/ko not_active Withdrawn
- 2012-05-09 PE PE2013002484A patent/PE20150105A1/es not_active Application Discontinuation
- 2012-05-09 EP EP12723010.0A patent/EP2707365B1/en not_active Not-in-force
- 2012-05-09 SG SG2013082730A patent/SG194846A1/en unknown
- 2012-05-09 BR BR112013028679A patent/BR112013028679A2/pt not_active IP Right Cessation
- 2012-05-09 CN CN201280034345.8A patent/CN103827108B/zh not_active Expired - Fee Related
- 2012-05-09 WO PCT/US2012/037012 patent/WO2012154777A1/en not_active Ceased
- 2012-05-09 PH PH1/2013/502177A patent/PH12013502177A1/en unknown
- 2012-05-09 JP JP2014510419A patent/JP5977819B2/ja not_active Expired - Fee Related
- 2012-05-09 CA CA2835688A patent/CA2835688A1/en not_active Abandoned
- 2012-05-09 EA EA201391685A patent/EA024201B1/ru not_active IP Right Cessation
- 2012-05-11 AR ARP120101698A patent/AR086389A1/es unknown
- 2012-05-11 UY UY0001034066A patent/UY34066A/es unknown
- 2012-05-11 TW TW101116982A patent/TW201249834A/zh unknown
-
2013
- 2013-11-07 MA MA36399A patent/MA35104B1/fr unknown
- 2013-11-07 IL IL229331A patent/IL229331A0/en unknown
- 2013-11-11 CL CL2013003229A patent/CL2013003229A1/es unknown
- 2013-12-09 CO CO13288206A patent/CO6821952A2/es not_active Application Discontinuation
- 2013-12-11 ZA ZA2013/09356A patent/ZA201309356B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BR112013028679A2 (pt) | 2017-01-24 |
| ZA201309356B (en) | 2015-05-27 |
| CO6821952A2 (es) | 2013-12-31 |
| UY34066A (es) | 2012-11-30 |
| EP2707365B1 (en) | 2018-10-17 |
| AR086389A1 (es) | 2013-12-11 |
| TW201249834A (en) | 2012-12-16 |
| PE20150105A1 (es) | 2015-02-06 |
| EA201391685A1 (ru) | 2014-03-31 |
| PH12013502177A1 (en) | 2014-01-13 |
| WO2012154777A1 (en) | 2012-11-15 |
| US9546160B2 (en) | 2017-01-17 |
| CL2013003229A1 (es) | 2014-09-05 |
| JP2014513690A (ja) | 2014-06-05 |
| SG194846A1 (en) | 2013-12-30 |
| JP5977819B2 (ja) | 2016-08-24 |
| IL229331A0 (en) | 2014-01-30 |
| MA35104B1 (fr) | 2014-05-02 |
| KR20140037114A (ko) | 2014-03-26 |
| AU2012253578A1 (en) | 2014-01-16 |
| CN103827108B (zh) | 2018-05-15 |
| CA2835688A1 (en) | 2012-11-15 |
| CN103827108A (zh) | 2014-05-28 |
| US20130121957A1 (en) | 2013-05-16 |
| EP2707365A1 (en) | 2014-03-19 |
| EA024201B1 (ru) | 2016-08-31 |
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