JP2012502101A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2012502101A5 JP2012502101A5 JP2011526931A JP2011526931A JP2012502101A5 JP 2012502101 A5 JP2012502101 A5 JP 2012502101A5 JP 2011526931 A JP2011526931 A JP 2011526931A JP 2011526931 A JP2011526931 A JP 2011526931A JP 2012502101 A5 JP2012502101 A5 JP 2012502101A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- phenyl
- fluorophenyl
- carboxamide
- cyclopropylcarbamoyl
- 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.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 claims 9
- 150000003839 salts Chemical class 0.000 claims 7
- -1 monofluorophenyl Chemical group 0.000 claims 5
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 150000003857 carboxamides Chemical class 0.000 claims 3
- 125000001475 halogen functional group Chemical group 0.000 claims 3
- 208000005176 Hepatitis C Diseases 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 208000010710 hepatitis C virus infection Diseases 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 108091032973 (ribonucleotides)n+m Proteins 0.000 claims 1
- UBCHPRBFMUDMNC-UHFFFAOYSA-N 1-(1-adamantyl)ethanamine Chemical compound C1C(C2)CC3CC2CC1(C(N)C)C3 UBCHPRBFMUDMNC-UHFFFAOYSA-N 0.000 claims 1
- ALTJZVSOJAJNKQ-UHFFFAOYSA-N 2-(4-fluorophenyl)-5-[4-methoxy-2-methyl-5-[(1-pyrimidin-2-ylcyclopropyl)carbamoyl]phenyl]-n-methyl-1-benzofuran-3-carboxamide Chemical compound C1=C2C(C(=O)NC)=C(C=3C=CC(F)=CC=3)OC2=CC=C1C(C(=CC=1OC)C)=CC=1C(=O)NC1(C=2N=CC=CN=2)CC1 ALTJZVSOJAJNKQ-UHFFFAOYSA-N 0.000 claims 1
- YTVCSPYLAXQBIC-UHFFFAOYSA-N 2-(4-fluorophenyl)-5-[4-methoxy-2-methyl-5-[[1-(3-methyl-1,2,4-oxadiazol-5-yl)cyclopropyl]carbamoyl]phenyl]-n-methyl-1-benzofuran-3-carboxamide Chemical compound C1=C2C(C(=O)NC)=C(C=3C=CC(F)=CC=3)OC2=CC=C1C(C(=CC=1OC)C)=CC=1C(=O)NC1(C=2ON=C(C)N=2)CC1 YTVCSPYLAXQBIC-UHFFFAOYSA-N 0.000 claims 1
- ISVFDRSHXWVAKJ-UHFFFAOYSA-N 2-(4-fluorophenyl)-5-[4-methoxy-2-methyl-5-[[1-(5-methyl-1,2,4-oxadiazol-3-yl)cyclopropyl]carbamoyl]phenyl]-n-methyl-1-benzofuran-3-carboxamide Chemical compound C1=C2C(C(=O)NC)=C(C=3C=CC(F)=CC=3)OC2=CC=C1C(C(=CC=1OC)C)=CC=1C(=O)NC1(C=2N=C(C)ON=2)CC1 ISVFDRSHXWVAKJ-UHFFFAOYSA-N 0.000 claims 1
- PAUHELJSJSVRPR-UHFFFAOYSA-N 2-(4-fluorophenyl)-6-[2-hydroxyethyl(methylsulfonyl)amino]-n-methyl-5-[3-(2-phenylpropan-2-ylcarbamoyl)phenyl]-1-benzofuran-3-carboxamide Chemical compound C1=C2C(C(=O)NC)=C(C=3C=CC(F)=CC=3)OC2=CC(N(CCO)S(C)(=O)=O)=C1C(C=1)=CC=CC=1C(=O)NC(C)(C)C1=CC=CC=C1 PAUHELJSJSVRPR-UHFFFAOYSA-N 0.000 claims 1
- TVJAATHIDLAWME-UHFFFAOYSA-N 2-(4-fluorophenyl)-6-[2-hydroxyethyl(methylsulfonyl)amino]-n-methyl-5-[3-[(1-phenylcyclopropyl)carbamoyl]phenyl]-1-benzofuran-3-carboxamide Chemical compound C1=C2C(C(=O)NC)=C(C=3C=CC(F)=CC=3)OC2=CC(N(CCO)S(C)(=O)=O)=C1C(C=1)=CC=CC=1C(=O)NC1(C=2C=CC=CC=2)CC1 TVJAATHIDLAWME-UHFFFAOYSA-N 0.000 claims 1
- LUIDEMBRIXHMJX-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-methyl-5-[2-methyl-5-[(1-pyrimidin-2-ylcyclopropyl)carbamoyl]phenyl]-1-benzofuran-3-carboxamide Chemical compound C1=C2C(C(=O)NC)=C(C=3C=CC(F)=CC=3)OC2=CC=C1C(C(=CC=1)C)=CC=1C(=O)NC1(C=2N=CC=CN=2)CC1 LUIDEMBRIXHMJX-UHFFFAOYSA-N 0.000 claims 1
- HRWYUZFUDWPPGO-UHFFFAOYSA-N 4-fluoro-2-(4-fluorophenyl)-5-[4-methoxy-2-methyl-5-[(1-pyrimidin-2-ylcyclopropyl)carbamoyl]phenyl]-n-methyl-1-benzofuran-3-carboxamide Chemical compound FC1=C2C(C(=O)NC)=C(C=3C=CC(F)=CC=3)OC2=CC=C1C(C(=CC=1OC)C)=CC=1C(=O)NC1(C=2N=CC=CN=2)CC1 HRWYUZFUDWPPGO-UHFFFAOYSA-N 0.000 claims 1
- WWXJVCIADCVMBJ-UHFFFAOYSA-N 5-[3-fluoro-2-methyl-5-[(1-pyridin-2-ylcyclopropyl)carbamoyl]phenyl]-2-(4-fluorophenyl)-n-methyl-1-benzofuran-3-carboxamide Chemical compound C1=C2C(C(=O)NC)=C(C=3C=CC(F)=CC=3)OC2=CC=C1C(C(=C(F)C=1)C)=CC=1C(=O)NC1(C=2N=CC=CC=2)CC1 WWXJVCIADCVMBJ-UHFFFAOYSA-N 0.000 claims 1
- 108020005544 Antisense RNA Proteins 0.000 claims 1
- 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 claims 1
- 108010036949 Cyclosporine Proteins 0.000 claims 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 1
- 239000005977 Ethylene Substances 0.000 claims 1
- 102000014150 Interferons Human genes 0.000 claims 1
- 108010050904 Interferons Proteins 0.000 claims 1
- 102000013462 Interleukin-12 Human genes 0.000 claims 1
- 108010065805 Interleukin-12 Proteins 0.000 claims 1
- 102000000588 Interleukin-2 Human genes 0.000 claims 1
- 108010002350 Interleukin-2 Proteins 0.000 claims 1
- 102000004889 Interleukin-6 Human genes 0.000 claims 1
- 108090001005 Interleukin-6 Proteins 0.000 claims 1
- 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 1
- 230000005867 T cell response Effects 0.000 claims 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
- DKNWSYNQZKUICI-UHFFFAOYSA-N amantadine Chemical compound C1C(C2)CC3CC2CC1(N)C3 DKNWSYNQZKUICI-UHFFFAOYSA-N 0.000 claims 1
- 229960003805 amantadine Drugs 0.000 claims 1
- 229960001265 ciclosporin Drugs 0.000 claims 1
- 239000003184 complementary RNA Substances 0.000 claims 1
- 229930182912 cyclosporin Natural products 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 210000002443 helper t lymphocyte Anatomy 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
- 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 1
- 229960002751 imiquimod Drugs 0.000 claims 1
- 239000002348 inosinate dehydrogenase inhibitor Substances 0.000 claims 1
- 230000002452 interceptive effect Effects 0.000 claims 1
- 229940079322 interferon Drugs 0.000 claims 1
- 229940117681 interleukin-12 Drugs 0.000 claims 1
- 229940100601 interleukin-6 Drugs 0.000 claims 1
- 125000000842 isoxazolyl group Chemical group 0.000 claims 1
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 229960000329 ribavirin Drugs 0.000 claims 1
- 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 1
- 229960000888 rimantadine Drugs 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 30
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-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 18
- 238000004128 high performance liquid chromatography Methods 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000003643 water by type Substances 0.000 description 4
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 3
- PXJGFPDYXKRNAY-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-benzofuran-3-carboxamide Chemical compound C1=C2C(C(=O)NC)=C(C=3C=CC(F)=CC=3)OC2=CC=C1B1OC(C)(C)C(C)(C)O1 PXJGFPDYXKRNAY-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000012267 brine Substances 0.000 description 3
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 230000014759 maintenance of location Effects 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 2
- WRMDENRTBINWAN-UHFFFAOYSA-N 3-bromo-5-hydroxy-n-(2-methylpropyl)benzamide Chemical compound CC(C)CNC(=O)C1=CC(O)=CC(Br)=C1 WRMDENRTBINWAN-UHFFFAOYSA-N 0.000 description 2
- PJFSCFUHMGZQOE-UHFFFAOYSA-N 3-bromo-n-(2-methylpropyl)-5-propan-2-yloxybenzamide Chemical compound CC(C)CNC(=O)C1=CC(Br)=CC(OC(C)C)=C1 PJFSCFUHMGZQOE-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- WGIBEMRBLBGETQ-UHFFFAOYSA-N 3-bromo-5-hydroxybenzoic acid Chemical compound OC(=O)C1=CC(O)=CC(Br)=C1 WGIBEMRBLBGETQ-UHFFFAOYSA-N 0.000 description 1
- 235000019502 Orange oil Nutrition 0.000 description 1
- 101150003085 Pdcl gene Proteins 0.000 description 1
- QXKGZIRQUOLYDG-UHFFFAOYSA-N [2-(4-fluorophenyl)-3-(methylcarbamoyl)-1-benzofuran-5-yl] trifluoromethanesulfonate Chemical compound O1C2=CC=C(OS(=O)(=O)C(F)(F)F)C=C2C(C(=O)NC)=C1C1=CC=C(F)C=C1 QXKGZIRQUOLYDG-UHFFFAOYSA-N 0.000 description 1
- IPWKHHSGDUIRAH-UHFFFAOYSA-N bis(pinacolato)diboron Chemical compound O1C(C)(C)C(C)(C)OB1B1OC(C)(C)C(C)(C)O1 IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 description 1
- 229940045348 brown mixture Drugs 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- FMKOJHQHASLBPH-UHFFFAOYSA-N isopropyl iodide Chemical compound CC(C)I FMKOJHQHASLBPH-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US9600508P | 2008-09-11 | 2008-09-11 | |
| US61/096,005 | 2008-09-11 | ||
| PCT/US2009/056166 WO2010030592A1 (en) | 2008-09-11 | 2009-09-08 | Compounds for the treatment of hepatitis c |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2012502101A JP2012502101A (ja) | 2012-01-26 |
| JP2012502101A5 true JP2012502101A5 (enExample) | 2014-09-04 |
| JP5685191B2 JP5685191B2 (ja) | 2015-03-18 |
Family
ID=41226922
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011526931A Expired - Fee Related JP5685191B2 (ja) | 2008-09-11 | 2009-09-08 | Ｃ型肝炎の治療のための化合物 |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US8048887B2 (enExample) |
| EP (1) | EP2326633B1 (enExample) |
| JP (1) | JP5685191B2 (enExample) |
| KR (1) | KR20110059875A (enExample) |
| CN (1) | CN102209717B (enExample) |
| AR (1) | AR073740A1 (enExample) |
| AU (1) | AU2009291966B2 (enExample) |
| BR (1) | BRPI0918174A2 (enExample) |
| CA (1) | CA2736988A1 (enExample) |
| CL (2) | CL2011000527A1 (enExample) |
| CO (1) | CO6382110A2 (enExample) |
| EA (1) | EA019185B1 (enExample) |
| IL (1) | IL211509A0 (enExample) |
| MX (1) | MX2011002410A (enExample) |
| NZ (1) | NZ591172A (enExample) |
| PE (1) | PE20110806A1 (enExample) |
| TW (2) | TW201014836A (enExample) |
| WO (1) | WO2010030592A1 (enExample) |
| ZA (2) | ZA201101739B (enExample) |
Families Citing this family (58)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7994171B2 (en) * | 2008-09-11 | 2011-08-09 | Bristol-Myers Squibb Company | Compounds for the treatment of hepatitis C |
| US8198449B2 (en) * | 2008-09-11 | 2012-06-12 | Bristol-Myers Squibb Company | Compounds for the treatment of hepatitis C |
| WO2010043721A1 (en) | 2008-10-17 | 2010-04-22 | Oryzon Genomics, S.A. | Oxidase inhibitors and their use |
| CA2741648A1 (en) * | 2008-10-30 | 2010-05-06 | Merck Sharp & Dohme Corp. | 2,5-disubstituted phenyl carboxamide orexin receptor antagonists |
| US8993808B2 (en) | 2009-01-21 | 2015-03-31 | Oryzon Genomics, S.A. | Phenylcyclopropylamine derivatives and their medical use |
| SG177308A1 (en) * | 2009-06-22 | 2012-02-28 | Hoffmann La Roche | Novel biphenyl and phenyl-pyridine amides |
| US8859555B2 (en) | 2009-09-25 | 2014-10-14 | Oryzon Genomics S.A. | Lysine Specific Demethylase-1 inhibitors and their use |
| EP2486002B1 (en) | 2009-10-09 | 2019-03-27 | Oryzon Genomics, S.A. | Substituted heteroaryl- and aryl- cyclopropylamine acetamides and their use |
| WO2011106573A2 (en) | 2010-02-24 | 2011-09-01 | Oryzon Genomics, S.A. | Lysine demethylase inhibitors for diseases and disorders associated with hepadnaviridae |
| US9616058B2 (en) | 2010-02-24 | 2017-04-11 | Oryzon Genomics, S.A. | Potent selective LSD1 inhibitors and dual LSD1/MAO-B inhibitors for antiviral use |
| US8324212B2 (en) | 2010-02-25 | 2012-12-04 | Bristol-Myers Squibb Company | Compounds for the treatment of hepatitis C |
| AR080433A1 (es) * | 2010-03-02 | 2012-04-11 | Merck Sharp & Dohme | Derivados de benzofurancarboxamidas utiles para tratar o prevenir infecciones por vhc y composiciones farmaceuticas que los contienen. |
| WO2011112191A1 (en) * | 2010-03-11 | 2011-09-15 | Bristol-Myers Squibb Company | Compounds for the treatment of hepatitis c |
| US8354410B2 (en) | 2010-03-11 | 2013-01-15 | Bristol-Meyers Squibb Company | Compounds for the treatment of hepatitis C |
| MX2012012111A (es) | 2010-04-19 | 2013-05-30 | Oryzon Genomics Sa | Inhibidores de demetilasa-1 especifica de lisina y su uso. |
| US8324239B2 (en) | 2010-04-21 | 2012-12-04 | Novartis Ag | Furopyridine compounds and uses thereof |
| WO2011140333A1 (en) | 2010-05-07 | 2011-11-10 | The Board Of Trustees Of The Leland Stanford Junior University | Identification of stabilizers of multimeric proteins |
| US8445497B2 (en) | 2010-06-30 | 2013-05-21 | Bristol-Myers Squibb Company | Compounds for the treatment of hepatitis C |
| WO2012013727A1 (en) | 2010-07-29 | 2012-02-02 | Oryzon Genomics S.A. | Cyclopropylamine derivatives useful as lsd1 inhibitors |
| SI2598482T1 (sl) | 2010-07-29 | 2018-09-28 | Oryzon Genomics, S.A. | Inhibitorji demetilaze lsd1 na osnovi arilciklopropilamina in njihova medicinska uporaba |
| EP2616461A4 (en) | 2010-08-26 | 2014-03-26 | Rfs Pharma Llc | POTENTIVE AND SELECTIVE INHIBITORS OF HEPATITIS C VIRUS |
| WO2012045883A1 (en) | 2010-10-08 | 2012-04-12 | Oryzon Genomics S.A. | Cyclopropylamine inhibitors of oxidases |
| CN103269586B (zh) | 2010-10-26 | 2015-07-15 | 普雷西迪奥制药公司 | 丙型肝炎病毒抑制剂 |
| WO2012072713A2 (en) | 2010-11-30 | 2012-06-07 | Oryzon Genomics, S.A. | Lysine demethylase inhibitors for diseases and disorders associated with flaviviridae |
| US8507683B2 (en) * | 2010-12-09 | 2013-08-13 | Bristol-Myers Squibb Company | Compounds for the treatment of hepatitis C |
| CN106986862A (zh) | 2010-12-22 | 2017-07-28 | Abbvie 公司 | 丙型肝炎抑制剂及其用途 |
| WO2012107498A1 (en) | 2011-02-08 | 2012-08-16 | Oryzon Genomics S.A. | Lysine demethylase inhibitors for myeloproliferative disorders |
| 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 |
| 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 |
| 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 |
| RS58475B1 (sr) | 2011-10-20 | 2019-04-30 | Oryzon Genomics Sa | Jedinjenja (hetero)aril ciklopropilamina kao lsd1 inhibitori |
| CN107266345B (zh) | 2011-10-20 | 2021-08-17 | 奥瑞泽恩基因组学股份有限公司 | 作为lsd1抑制剂的(杂)芳基环丙胺化合物 |
| US9303020B2 (en) | 2012-02-08 | 2016-04-05 | Bristol-Myers Squibb Company | Compounds for the treatment of hepatitis C |
| EP2831066B1 (en) | 2012-03-27 | 2016-10-05 | Bristol-Myers Squibb Company | Benzofuran derivatives for the treatment of hepatitis c |
| WO2013163466A1 (en) * | 2012-04-25 | 2013-10-31 | Presidio Pharmaceuticals, Inc. | Inhibitors of hepatitis c virus |
| US9169214B2 (en) | 2012-12-21 | 2015-10-27 | The Board Of Trustees Of The Leland Stanford Junior University | Compounds and compositions that bind and stabilize transthyretin and their use for inhibiting transthyretin amyloidosis and protein-protein interactions |
| JP2016505011A (ja) * | 2013-01-10 | 2016-02-18 | ブリストル−マイヤーズ スクイブ カンパニーＢｒｉｓｔｏｌ−Ｍｙｅｒｓ Ｓｑｕｉｂｂ Ｃｏｍｐａｎｙ | Ｃ型肝炎の治療用の大環状ベンゾフランおよびアザベンゾフラン化合物 |
| WO2014121416A1 (en) | 2013-02-07 | 2014-08-14 | Merck Sharp & Dohme Corp. | Tetracyclic heterocycle compounds and methods of use thereof for the treatment of hepatitis c |
| US8962651B2 (en) | 2013-03-13 | 2015-02-24 | Bristol-Myers Squibb Company | Compounds for the treatment of hepatitis C |
| EP2970174B1 (en) * | 2013-03-14 | 2017-05-03 | Bristol-Myers Squibb Company | Fused furans for the treatment of hepatitis c |
| WO2014205593A1 (en) * | 2013-06-24 | 2014-12-31 | Merck Sharp & Dohme Corp. | Substituted benzofuran compounds and methods of use thereof for treatment of viral diseases |
| WO2015088958A1 (en) * | 2013-12-13 | 2015-06-18 | Bristol-Myers Squibb Company | A novel compound for the treatment of hepatitis c |
| ES2688554T3 (es) * | 2014-03-21 | 2018-11-05 | Bristol-Myers Squibb Company | Compuestos de azabenzofurano que contienen ciano para el tratamiento de la hepatitis C |
| EP3119769A1 (en) * | 2014-03-21 | 2017-01-25 | Bristol-Myers Squibb Pharma Company | Cyanoamino (aza)benzofuran compounds for the treatment of hepatitis c |
| US20160045609A1 (en) | 2014-08-14 | 2016-02-18 | Mamoun M. Alhamadsheh | Conjugation of pharmaceutically active agents with transthyretin ligands through adjustable linkers to increase serum half-life |
| WO2016133963A1 (en) * | 2015-02-19 | 2016-08-25 | Bristol-Myers Squibb Company | Benzofurans substituted with secondary benzamide as hcv inhibitors |
| WO2016133961A1 (en) * | 2015-02-19 | 2016-08-25 | Bristol-Myers Squibb Company | Benzofurans substituted with bicyclic secondary benzamide as hcv inhibitors |
| US10131645B2 (en) | 2015-02-19 | 2018-11-20 | Bristol-Myers Squibb Company | Benzofurans substituted with primary benzamide as HCV inhibitors |
| US10570108B2 (en) | 2015-02-19 | 2020-02-25 | Bristol-Myers Squibb Company | Substituted benzofuran compounds for the treatment of hepatitis C |
| CN107406435A (zh) * | 2015-02-23 | 2017-11-28 | 百时美施贵宝公司 | 新的治疗丙型肝炎的化合物 |
| US11161837B2 (en) | 2016-03-21 | 2021-11-02 | Bristol-Myers Squibb Company | Benzofuran derivatives for the treatment of hepatitis C |
| CN116730920A (zh) | 2017-02-17 | 2023-09-12 | 文涵治疗有限公司 | Ag-10的制备方法、其中间体及其盐 |
| KR102512548B1 (ko) | 2017-12-22 | 2023-03-22 | 삼성디스플레이 주식회사 | 유기 전계 발광 소자 및 유기 전계 발광 소자용 함질소 화합물 |
| MA52137A (fr) | 2018-03-23 | 2021-01-27 | Eidos Therapeutics Inc | Méthodes de traitement de l'amylose ttr à l'aide d'ag10 |
| AU2019321583C1 (en) | 2018-08-17 | 2025-11-27 | Eidos Therapeutics, Inc. | Formulations of AG10 |
| EP3886854A4 (en) | 2018-11-30 | 2022-07-06 | Nuvation Bio Inc. | Pyrrole and pyrazole compounds and methods of use thereof |
| CN114174283B (zh) * | 2019-07-18 | 2023-05-12 | 石药集团中奇制药技术（石家庄）有限公司 | 作为nmt抑制剂的化合物及其应用 |
| WO2025147320A1 (en) * | 2024-01-03 | 2025-07-10 | Kymera Therapeutics, Inc. | Stat6 inhibitors and uses thereof |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57123181A (en) | 1981-01-23 | 1982-07-31 | Mitsubishi Paper Mills Ltd | Preparation of pyrazolo (1,5-a) pyridine derivative |
| PE20020506A1 (es) | 2000-08-22 | 2002-07-09 | Glaxo Group Ltd | Derivados de pirazol fusionados como inhibidores de la proteina cinasa |
| EP1372642A1 (en) | 2001-03-30 | 2004-01-02 | SmithKline Beecham Corporation | Use of pyrazolopyridines as therapeutic compounds |
| UA79834C2 (en) * | 2002-11-01 | 2007-07-25 | Viropharma Inc | Benzofuran compounds, compositions and methods for treatment and prophylaxis of hepatitis c viral infections and associated diseases |
| US7868037B2 (en) * | 2004-07-14 | 2011-01-11 | Ptc Therapeutics, Inc. | Methods for treating hepatitis C |
| TW200815384A (en) * | 2006-08-25 | 2008-04-01 | Viropharma Inc | Combination therapy method for treating hepatitis C virus infection and pharmaceutical compositions for use therein |
| EP2134683A2 (en) * | 2007-02-12 | 2009-12-23 | Intermune, Inc. | Novel inhibitors hepatitis c virus replication |
| GB0707000D0 (en) | 2007-04-12 | 2007-05-30 | Istituto Di Ricerche D Biolog | Antiviral agents |
| JP2011512341A (ja) | 2008-02-14 | 2011-04-21 | エフ．ホフマン−ラ ロシュ アーゲー | 抗ウイルス性複素環化合物 |
| WO2009137500A1 (en) | 2008-05-05 | 2009-11-12 | Wyeth | 6-substituted benzofuran compounds to treat infection with hepatitis c virus |
| WO2009137493A1 (en) | 2008-05-05 | 2009-11-12 | Wyeth | 2-substituted benzofuran compounds to treat infection with hepatitis c virus |
-
2009
- 2009-09-04 US US12/554,193 patent/US8048887B2/en active Active
- 2009-09-08 KR KR1020117008085A patent/KR20110059875A/ko not_active Ceased
- 2009-09-08 EP EP09792299.1A patent/EP2326633B1/en not_active Not-in-force
- 2009-09-08 CA CA2736988A patent/CA2736988A1/en not_active Abandoned
- 2009-09-08 BR BRPI0918174A patent/BRPI0918174A2/pt not_active IP Right Cessation
- 2009-09-08 JP JP2011526931A patent/JP5685191B2/ja not_active Expired - Fee Related
- 2009-09-08 NZ NZ591172A patent/NZ591172A/xx not_active IP Right Cessation
- 2009-09-08 WO PCT/US2009/056166 patent/WO2010030592A1/en not_active Ceased
- 2009-09-08 EA EA201100390A patent/EA019185B1/ru not_active IP Right Cessation
- 2009-09-08 PE PE2011000445A patent/PE20110806A1/es active IP Right Grant
- 2009-09-08 MX MX2011002410A patent/MX2011002410A/es active IP Right Grant
- 2009-09-08 AU AU2009291966A patent/AU2009291966B2/en not_active Ceased
- 2009-09-08 CN CN200980144912.3A patent/CN102209717B/zh not_active Expired - Fee Related
- 2009-09-11 TW TW098130829A patent/TW201014836A/zh unknown
- 2009-09-11 TW TW100113021A patent/TW201124403A/zh unknown
- 2009-09-11 AR ARP090103514A patent/AR073740A1/es not_active Application Discontinuation
-
2011
- 2011-03-01 ZA ZA2011/01739A patent/ZA201101739B/en unknown
- 2011-03-01 IL IL211509A patent/IL211509A0/en unknown
- 2011-03-11 CL CL2011000527A patent/CL2011000527A1/es unknown
- 2011-04-05 CO CO11041979A patent/CO6382110A2/es not_active Application Discontinuation
- 2011-05-25 CL CL2011001224A patent/CL2011001224A1/es unknown
- 2011-08-03 ZA ZA2011/05720A patent/ZA201105720B/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP7646632B2 (ja) | 甲状腺ホルモン受容体ベータアゴニスト化合物 | |
| AU2017387695B2 (en) | (Aza)indole-, benzothiophene-, and benzofuran-3-sulfonamides | |
| JP6528957B2 (ja) | Ｔｒｋ阻害化合物 | |
| JP2023515728A (ja) | Ｃｄｋ阻害剤としてのピリジンアセトアミド系誘導体、その調製方法及び用途 | |
| EP1586571B3 (en) | Dipeptidyl peptidase inhibitors | |
| JP6121393B2 (ja) | Ｊｕｎｎ−末端キナーゼの阻害薬 | |
| ES2336470T3 (es) | Piperidinas sustituidas como inhibidores de renina. | |
| ES2694829T3 (es) | Derivados de benzotriazol trisustituido como inhibidores de dihidroorotato oxigenasa | |
| JP5640006B2 (ja) | ヒストン脱アセチル化酵素および／またはサイクリン依存性キナーゼの縮合複素環式阻害剤 | |
| CA2825172A1 (en) | Indole derivative and pharmacologically acceptable salt of same | |
| TWI469977B (zh) | ７－苯氧基唍羧酸衍生物 | |
| JP2020502103A (ja) | Ｃｆｔｒ増強物質としての二環式ヘテロアリール誘導体 | |
| KR101866706B1 (ko) | 1-알킬-6-옥소-1,6-디하이드로피리딘-3-일 화합물과 sgrm 조절인자로서의 용도 | |
| SK282338B6 (sk) | N-Heteroarylpyridínsulfónamidové deriváty, spôsob prípravy, medziprodukty a použitie týchto derivátov ako antagonistov endotelínu | |
| KR20100016076A (ko) | 신규 피롤리논 유도체 및 그것을 함유하는 의약 조성물 | |
| JP2010111624A (ja) | Ｔｔｋ阻害作用を有するインダゾール誘導体 | |
| JP2022532719A (ja) | Ａｃｓｓ２阻害剤およびその使用方法 | |
| US12291523B2 (en) | LXR modulators with bicyclic core moiety | |
| JP7624404B2 (ja) | Ｐｒｃ２阻害剤としてのナフチリジン誘導体 | |
| WO2019101086A1 (zh) | 卤代烯丙基胺类ssao/vap-1抑制剂及其应用 | |
| AU2018303186A1 (en) | Amine or (thio)amide containing LXR modulators | |
| US20120252853A1 (en) | Positive allosteric modulators of nicotinic acetylcholine receptor | |
| ES2645847T3 (es) | Derivado de glicinamida alfa-sustituido | |
| EP3189060B1 (fr) | Derives de n-aryl-2-amino-4-aryl-pyrimidines polyethers macrocycliques comme inhibiteurs de la ftl3 and jak | |
| ES2641469T3 (es) | Compuesto de 2-piridona |