JP2013056886A5 - - Google Patents
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- Publication number
- JP2013056886A5 JP2013056886A5 JP2012221886A JP2012221886A JP2013056886A5 JP 2013056886 A5 JP2013056886 A5 JP 2013056886A5 JP 2012221886 A JP2012221886 A JP 2012221886A JP 2012221886 A JP2012221886 A JP 2012221886A JP 2013056886 A5 JP2013056886 A5 JP 2013056886A5
- Authority
- JP
- Japan
- Prior art keywords
- dioxo
- tert
- butyl
- dihydropyrimidin
- naphthalen
- 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
- 239000013078 crystal Substances 0.000 claims 79
- 238000000634 powder X-ray diffraction Methods 0.000 claims 54
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims 47
- 239000003814 drug Substances 0.000 claims 45
- -1 6- (3-tert-butyl-5- (2,4-dioxo-3,4-dihydropyrimidin-1 (2H) -yl) -2-methoxyphenyl) naphthalen-2-yl Chemical group 0.000 claims 38
- 239000003112 inhibitor Substances 0.000 claims 36
- 229940124597 therapeutic agent Drugs 0.000 claims 35
- 241000711549 Hepacivirus C Species 0.000 claims 31
- QICWSAFHNDKQKS-UHFFFAOYSA-N sodium;methylsulfonylazanide Chemical compound [Na+].CS([NH-])(=O)=O QICWSAFHNDKQKS-UHFFFAOYSA-N 0.000 claims 26
- 125000000845 uracil-1-yl group Chemical group [*]N1C(=O)N([H])C(=O)C([H])=C1[H] 0.000 claims 24
- 239000012453 solvate Substances 0.000 claims 22
- CNUGIPSJLQIKHL-UHFFFAOYSA-N n-[6-[3-tert-butyl-5-(2,4-dioxopyrimidin-1-yl)-2-methoxyphenyl]naphthalen-2-yl]methanesulfonamide;sodium Chemical compound [Na].C1=C(C(C)(C)C)C(OC)=C(C=2C=C3C=CC(NS(C)(=O)=O)=CC3=CC=2)C=C1N1C=CC(=O)NC1=O CNUGIPSJLQIKHL-UHFFFAOYSA-N 0.000 claims 17
- 239000008194 pharmaceutical composition Substances 0.000 claims 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 15
- 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 13
- 229960000329 ribavirin Drugs 0.000 claims 13
- 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 13
- 238000000034 method Methods 0.000 claims 11
- 102000014150 Interferons Human genes 0.000 claims 8
- 108010050904 Interferons Proteins 0.000 claims 8
- 241000124008 Mammalia Species 0.000 claims 8
- 229940079593 drug Drugs 0.000 claims 8
- 229940079322 interferon Drugs 0.000 claims 8
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims 7
- 239000000203 mixture Substances 0.000 claims 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 6
- RORVQFXACWAYHO-UHFFFAOYSA-N OCC[N+](C)(C)C.CS(=O)(=O)[NH-] Chemical compound OCC[N+](C)(C)C.CS(=O)(=O)[NH-] RORVQFXACWAYHO-UHFFFAOYSA-N 0.000 claims 6
- 150000001408 amides Chemical class 0.000 claims 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 6
- 229920002477 rna polymer Polymers 0.000 claims 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 5
- 229940042399 direct acting antivirals protease inhibitors Drugs 0.000 claims 5
- 239000000137 peptide hydrolase inhibitor Substances 0.000 claims 5
- 208000005176 Hepatitis C Diseases 0.000 claims 4
- XNKPMUBPFWXXAD-UHFFFAOYSA-N O.CS(N)(=O)=O Chemical compound O.CS(N)(=O)=O XNKPMUBPFWXXAD-UHFFFAOYSA-N 0.000 claims 4
- YLJJDRHCFSYNQC-UHFFFAOYSA-N C(C)#N.CS(=O)(=O)N Chemical compound C(C)#N.CS(=O)(=O)N YLJJDRHCFSYNQC-UHFFFAOYSA-N 0.000 claims 3
- QIGVQMQJYXFLBW-UHFFFAOYSA-N C(CC)O.CS(=O)(=O)N Chemical compound C(CC)O.CS(=O)(=O)N QIGVQMQJYXFLBW-UHFFFAOYSA-N 0.000 claims 3
- OULVDSKBPHRFOK-UHFFFAOYSA-N CC(C)O.CS(=O)(=O)N Chemical compound CC(C)O.CS(=O)(=O)N OULVDSKBPHRFOK-UHFFFAOYSA-N 0.000 claims 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- JLXZKWMNOQXBCH-UHFFFAOYSA-N OCC[N+](C)(C)C.OCC[N+](C)(C)C.CS(=O)(=O)[NH-].CS(=O)(=O)[NH-] Chemical compound OCC[N+](C)(C)C.OCC[N+](C)(C)C.CS(=O)(=O)[NH-].CS(=O)(=O)[NH-] JLXZKWMNOQXBCH-UHFFFAOYSA-N 0.000 claims 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- NBRBXGKOEOGLOI-UHFFFAOYSA-N dasabuvir Chemical compound C1=C(C(C)(C)C)C(OC)=C(C=2C=C3C=CC(NS(C)(=O)=O)=CC3=CC=2)C=C1N1C=CC(=O)NC1=O NBRBXGKOEOGLOI-UHFFFAOYSA-N 0.000 claims 3
- 241001493065 dsRNA viruses Species 0.000 claims 3
- GIUFIPWVKLDKIG-UHFFFAOYSA-N ethanol;methanesulfonamide Chemical compound CCO.CS(N)(=O)=O GIUFIPWVKLDKIG-UHFFFAOYSA-N 0.000 claims 3
- OYGTWWUMEFMIMY-UHFFFAOYSA-N methanesulfonamide methanol Chemical compound CO.CS(=O)(=O)N OYGTWWUMEFMIMY-UHFFFAOYSA-N 0.000 claims 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims 3
- JBCZHFZUGPROKE-UHFFFAOYSA-N potassium methylsulfonylazanide Chemical compound [K+].CS(=O)(=O)[NH-] JBCZHFZUGPROKE-UHFFFAOYSA-N 0.000 claims 3
- 229910052708 sodium Inorganic materials 0.000 claims 3
- 239000011734 sodium Substances 0.000 claims 3
- 239000002904 solvent Substances 0.000 claims 3
- 230000029812 viral genome replication Effects 0.000 claims 3
- ZKYCMIKRCPXEPT-UHFFFAOYSA-N 2-(methanesulfonamido)ethyl acetate Chemical compound C(C)(=O)OCCNS(=O)(=O)C ZKYCMIKRCPXEPT-UHFFFAOYSA-N 0.000 claims 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 2
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 claims 2
- CMRCKCWAEWYWRN-UHFFFAOYSA-N [Na+].[Na+].CS(=O)(=O)[NH-].CS(=O)(=O)[NH-] Chemical compound [Na+].[Na+].CS(=O)(=O)[NH-].CS(=O)(=O)[NH-] CMRCKCWAEWYWRN-UHFFFAOYSA-N 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- NULCVGURSXLCOK-UHFFFAOYSA-N n-[6-[3-tert-butyl-5-(2,4-dioxopyrimidin-1-yl)-2-methoxyphenyl]naphthalen-2-yl]methanesulfonamide;2-hydroxyethyl(trimethyl)azanium Chemical compound C[N+](C)(C)CCO.C1=C(C(C)(C)C)C(OC)=C(C=2C=C3C=CC(NS(C)(=O)=O)=CC3=CC=2)C=C1N1C=CC(=O)NC1=O NULCVGURSXLCOK-UHFFFAOYSA-N 0.000 claims 2
- 238000002360 preparation method Methods 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 159000000000 sodium salts Chemical class 0.000 claims 2
- 238000007614 solvation Methods 0.000 claims 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 claims 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical class [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims 1
- MGCVGJVQIPYNKV-UHFFFAOYSA-N ethyl 2-(methanesulfonamido)acetate Chemical compound CCOC(=O)CNS(C)(=O)=O MGCVGJVQIPYNKV-UHFFFAOYSA-N 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 150000004677 hydrates Chemical class 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- KPPQIKYWDKLYMC-UHFFFAOYSA-N methanesulfonamide;sodium Chemical compound [Na].CS(N)(=O)=O KPPQIKYWDKLYMC-UHFFFAOYSA-N 0.000 claims 1
- BEJJPPNTXTWMGM-UHFFFAOYSA-N n-[6-[3-tert-butyl-5-(2,4-dioxopyrimidin-1-yl)-2-methoxyphenyl]naphthalen-2-yl]methanesulfonamide;sodium Chemical compound [Na].[Na].C1=C(C(C)(C)C)C(OC)=C(C=2C=C3C=CC(NS(C)(=O)=O)=CC3=CC=2)C=C1N1C=CC(=O)NC1=O BEJJPPNTXTWMGM-UHFFFAOYSA-N 0.000 claims 1
- 238000010899 nucleation Methods 0.000 claims 1
- 239000000843 powder Substances 0.000 claims 1
- 230000010076 replication Effects 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US97288107P | 2007-09-17 | 2007-09-17 | |
| US60/972,881 | 2007-09-17 | ||
| US9679208P | 2008-09-13 | 2008-09-13 | |
| US61/096,792 | 2008-09-13 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010525103A Division JP5734655B2 (ja) | 2007-09-17 | 2008-09-17 | 抗感染症ピリミジンおよびその使用 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013056886A JP2013056886A (ja) | 2013-03-28 |
| JP2013056886A5 true JP2013056886A5 (https=) | 2013-10-24 |
| JP5931683B2 JP5931683B2 (ja) | 2016-06-08 |
Family
ID=40308557
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010525103A Expired - Fee Related JP5734655B2 (ja) | 2007-09-17 | 2008-09-17 | 抗感染症ピリミジンおよびその使用 |
| JP2012221886A Expired - Fee Related JP5931683B2 (ja) | 2007-09-17 | 2012-10-04 | 抗感染症ピリミジンおよびその使用 |
| JP2015082240A Pending JP2015187106A (ja) | 2007-09-17 | 2015-04-14 | 抗感染症ピリミジンおよびその使用 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010525103A Expired - Fee Related JP5734655B2 (ja) | 2007-09-17 | 2008-09-17 | 抗感染症ピリミジンおよびその使用 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015082240A Pending JP2015187106A (ja) | 2007-09-17 | 2015-04-14 | 抗感染症ピリミジンおよびその使用 |
Country Status (21)
| Country | Link |
|---|---|
| US (3) | US8188104B2 (https=) |
| EP (3) | EP2203431B1 (https=) |
| JP (3) | JP5734655B2 (https=) |
| CN (4) | CN101842360B (https=) |
| AT (1) | ATE519746T1 (https=) |
| CA (2) | CA2699986C (https=) |
| CY (3) | CY1115514T1 (https=) |
| DK (3) | DK2639226T3 (https=) |
| ES (3) | ES2592961T3 (https=) |
| HR (2) | HRP20110809T1 (https=) |
| HU (1) | HUS1500013I1 (https=) |
| LT (1) | LTC2203431I2 (https=) |
| LU (1) | LU92666I2 (https=) |
| MX (1) | MX2010002902A (https=) |
| NL (1) | NL300729I1 (https=) |
| NO (1) | NO2015011I1 (https=) |
| PL (3) | PL2639226T3 (https=) |
| PT (3) | PT2639226T (https=) |
| RU (2) | RU2539570C2 (https=) |
| SI (2) | SI2368882T1 (https=) |
| WO (1) | WO2009039134A1 (https=) |
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| PL2639226T3 (pl) * | 2007-09-17 | 2017-02-28 | Abbvie Bahamas Ltd. | Pirymidyny o działaniu przeciw zakaźnym oraz ich zastosowania |
| CN101918369B (zh) | 2007-09-17 | 2016-02-24 | 艾伯维巴哈马有限公司 | 治疗丙型肝炎的尿嘧啶或胸腺嘧啶衍生物 |
| PA8796201A1 (es) | 2007-09-17 | 2009-04-23 | Abbott Lab | Agentes anti-infecciosos y su uso |
| EP2307372B1 (en) * | 2008-07-23 | 2012-04-25 | F. Hoffmann-La Roche AG | Heterocyclic antiviral compounds |
| CN102164909A (zh) | 2008-09-26 | 2011-08-24 | 弗·哈夫曼-拉罗切有限公司 | 用于治疗hcv的吡啶或吡嗪衍生物 |
| WO2010043721A1 (en) | 2008-10-17 | 2010-04-22 | Oryzon Genomics, S.A. | Oxidase inhibitors and their use |
| US8993808B2 (en) | 2009-01-21 | 2015-03-31 | Oryzon Genomics, S.A. | Phenylcyclopropylamine derivatives and their medical use |
| MX2011010047A (es) * | 2009-03-25 | 2011-10-11 | Abbott Lab | Compuestos antivirales y usos de los mismos. |
| JP2012524752A (ja) | 2009-04-25 | 2012-10-18 | エフ.ホフマン−ラ ロシュ アーゲー | 複素環式抗ウイルス化合物 |
| AR077004A1 (es) | 2009-06-09 | 2011-07-27 | Hoffmann La Roche | Compuestos heterociclicos antivirales |
| MX2011012541A (es) | 2009-06-24 | 2012-08-03 | Hoffmann La Roche | Compuestos heterociclicos antivirales. |
| CA2768924A1 (en) | 2009-09-21 | 2011-03-24 | F. Hoffmann-La Roche Ag | Heterocyclic antiviral compounds |
| 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 |
| CN102639504A (zh) * | 2009-11-21 | 2012-08-15 | 弗·哈夫曼-拉罗切有限公司 | 杂环抗病毒化合物 |
| MX2012006776A (es) * | 2009-12-14 | 2012-10-05 | Merck Patent Gmbh | Inhibidores de la esfingosina quinasa. |
| CA2780526A1 (en) * | 2009-12-14 | 2011-06-23 | F. Hoffmann-La Roche Ag | Heterocyclic antiviral compounds |
| WO2011106574A2 (en) | 2010-02-24 | 2011-09-01 | Oryzon Genomics, S.A. | Inhibitors for antiviral use |
| WO2011106106A2 (en) | 2010-02-24 | 2011-09-01 | Oryzon Genomics, S.A. | Lysine demethylase inhibitors for diseases and disorders associated with hepadnaviridae |
| US9216952B2 (en) | 2010-03-23 | 2015-12-22 | Abbvie Inc. | Process for preparing antiviral compound |
| CA2796726C (en) | 2010-04-19 | 2021-02-16 | Oryzon Genomics S.A. | Lysine specific demethylase-1 inhibitors and their use |
| US8975443B2 (en) | 2010-07-16 | 2015-03-10 | Abbvie Inc. | Phosphine ligands for catalytic reactions |
| US9255074B2 (en) | 2010-07-16 | 2016-02-09 | Abbvie Inc. | Process for preparing antiviral compounds |
| SG187103A1 (en) | 2010-07-16 | 2013-02-28 | Abbvie Inc | Phosphine ligands for catalytic reactions |
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| BR112013002164B1 (pt) | 2010-07-29 | 2021-11-09 | Oryzon Genomics S.A. | Inibidores de desmetilase à base de arilciclopropilamina de lsd1, seus usos, e composição farmacêutica |
| US9006449B2 (en) | 2010-07-29 | 2015-04-14 | Oryzon Genomics, S.A. | Cyclopropylamine derivatives useful as LSD1 inhibitors |
| WO2012020725A1 (ja) * | 2010-08-10 | 2012-02-16 | 塩野義製薬株式会社 | Npy y5受容体拮抗作用を有するヘテロ環誘導体 |
| US9061966B2 (en) | 2010-10-08 | 2015-06-23 | Oryzon Genomics S.A. | Cyclopropylamine inhibitors of oxidases |
| WO2012072713A2 (en) * | 2010-11-30 | 2012-06-07 | Oryzon Genomics, S.A. | Lysine demethylase inhibitors for diseases and disorders associated with flaviviridae |
| EP2712315B1 (en) | 2011-02-08 | 2021-11-24 | Oryzon Genomics, S.A. | Lysine demethylase inhibitors for myeloproliferative disorders |
| CN102675092B (zh) * | 2011-03-14 | 2014-11-05 | 江苏中丹药物研究有限公司 | 一种制备2-芳基-2,2-二甲基乙酸甲酯的方法 |
| US10201584B1 (en) | 2011-05-17 | 2019-02-12 | Abbvie Inc. | Compositions and methods for treating HCV |
| EP2768805B1 (en) | 2011-10-20 | 2020-03-25 | Oryzon Genomics, S.A. | (hetero)aryl cyclopropylamine compounds as lsd1 inhibitors |
| JP6046154B2 (ja) | 2011-10-20 | 2016-12-14 | オリソン ヘノミクス エセ. アー. | Lsd1阻害剤としての(ヘテロ)アリールシクロプロピルアミン化合物 |
| EP2583677A3 (en) | 2011-10-21 | 2013-07-03 | Abbvie Inc. | Methods for treating HCV comprising at least two direct acting antiviral agent, ribavirin but not interferon. |
| US8492386B2 (en) | 2011-10-21 | 2013-07-23 | Abbvie Inc. | Methods for treating HCV |
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| CA3017751A1 (en) * | 2016-03-17 | 2017-09-21 | Fmc Corporation | Process for converting s-enantiomer to its racemic form |
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| CN111518036A (zh) * | 2020-04-29 | 2020-08-11 | 杭州勇诚睿生物科技有限公司 | 一种达沙布韦关键中间体的制备方法 |
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| CN117466847B (zh) * | 2022-07-22 | 2026-01-27 | 中国医药工业研究总院有限公司 | 一种利非斯特中间体苯并呋喃-6-羧酸的制备方法 |
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| AR057986A1 (es) * | 2005-11-21 | 2008-01-09 | Japan Tobacco Inc | Compuesto heterociclico y su uso farmaceutico |
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| CN101918369B (zh) | 2007-09-17 | 2016-02-24 | 艾伯维巴哈马有限公司 | 治疗丙型肝炎的尿嘧啶或胸腺嘧啶衍生物 |
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