JP2013520507A5 - - Google Patents
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- Publication number
- JP2013520507A5 JP2013520507A5 JP2012555088A JP2012555088A JP2013520507A5 JP 2013520507 A5 JP2013520507 A5 JP 2013520507A5 JP 2012555088 A JP2012555088 A JP 2012555088A JP 2012555088 A JP2012555088 A JP 2012555088A JP 2013520507 A5 JP2013520507 A5 JP 2013520507A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- phenyl
- hydrogen
- substituted
- alkoxy
- 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.)
- Ceased
Links
- 125000000217 alkyl group Chemical group 0.000 claims 45
- 239000001257 hydrogen Substances 0.000 claims 33
- 229910052739 hydrogen Inorganic materials 0.000 claims 33
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 30
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 26
- 125000005843 halogen group Chemical group 0.000 claims 21
- 125000003545 alkoxy group Chemical group 0.000 claims 17
- 150000003839 salts Chemical class 0.000 claims 16
- 150000001875 compounds Chemical class 0.000 claims 15
- 125000004076 pyridyl group Chemical group 0.000 claims 13
- 125000001424 substituent group Chemical group 0.000 claims 12
- -1 dioxothiazinyl Chemical group 0.000 claims 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims 7
- 150000002431 hydrogen Chemical class 0.000 claims 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 5
- 229910052757 nitrogen Inorganic materials 0.000 claims 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 5
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 4
- 125000002393 azetidinyl group Chemical group 0.000 claims 4
- 125000005059 halophenyl group Chemical group 0.000 claims 4
- 125000000842 isoxazolyl group Chemical group 0.000 claims 4
- 125000002757 morpholinyl group Chemical group 0.000 claims 4
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 4
- 125000002971 oxazolyl group Chemical group 0.000 claims 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 4
- 125000004193 piperazinyl group Chemical group 0.000 claims 4
- 125000003386 piperidinyl group Chemical group 0.000 claims 4
- 125000003373 pyrazinyl group Chemical group 0.000 claims 4
- 125000003226 pyrazolyl group Chemical group 0.000 claims 4
- 125000002098 pyridazinyl group Chemical group 0.000 claims 4
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 4
- 125000004306 triazinyl group Chemical group 0.000 claims 4
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 3
- 125000001188 haloalkyl group Chemical group 0.000 claims 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 3
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 2
- 239000005977 Ethylene Substances 0.000 claims 2
- 208000005176 Hepatitis C Diseases 0.000 claims 2
- 125000005036 alkoxyphenyl group Chemical group 0.000 claims 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 208000010710 hepatitis C virus infection Diseases 0.000 claims 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 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
- PHATVHUGCPSWJF-UHFFFAOYSA-N 2-(4-fluorophenyl)-5-[4-methoxy-2-methyl-5-[(1-phenylcyclopropyl)carbamoyl]phenyl]-n-methylpyrazolo[1,5-b]pyridazine-3-carboxamide Chemical compound C=1C2=C(C(=O)NC)C(C=3C=CC(F)=CC=3)=NN2N=CC=1C(C(=CC=1OC)C)=CC=1C(=O)NC1(C=2C=CC=CC=2)CC1 PHATVHUGCPSWJF-UHFFFAOYSA-N 0.000 claims 1
- VAEVSTUVTLPPJR-UHFFFAOYSA-N 2-(4-fluorophenyl)-5-[4-methoxy-2-methyl-5-[(1-pyrimidin-2-ylcyclopropyl)carbamoyl]phenyl]-n-methylpyrazolo[1,5-b]pyridazine-3-carboxamide Chemical compound C=1C2=C(C(=O)NC)C(C=3C=CC(F)=CC=3)=NN2N=CC=1C(C(=CC=1OC)C)=CC=1C(=O)NC1(C=2N=CC=CN=2)CC1 VAEVSTUVTLPPJR-UHFFFAOYSA-N 0.000 claims 1
- NJUZUQINYCJCBZ-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-methyl-5-[2-methyl-5-[(1-phenylcyclopropyl)carbamoyl]phenyl]pyrazolo[1,5-b]pyridazine-3-carboxamide Chemical compound C=1C2=C(C(=O)NC)C(C=3C=CC(F)=CC=3)=NN2N=CC=1C(C(=CC=1)C)=CC=1C(=O)NC1(C=2C=CC=CC=2)CC1 NJUZUQINYCJCBZ-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
- 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
- 125000004448 alkyl carbonyl 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
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 229960001265 ciclosporin Drugs 0.000 claims 1
- 239000003184 complementary RNA Substances 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 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
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000006485 halo alkoxy phenyl group Chemical group 0.000 claims 1
- 125000004692 haloalkylcarbonyl group Chemical group 0.000 claims 1
- 210000002443 helper t lymphocyte Anatomy 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
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims 1
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 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
- 125000003831 tetrazolyl group Chemical group 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- 125000001425 triazolyl group Chemical group 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US30808410P | 2010-02-25 | 2010-02-25 | |
| US61/308,084 | 2010-02-25 | ||
| PCT/US2011/025803 WO2011106340A1 (en) | 2010-02-25 | 2011-02-23 | Pyrazolopyridazine derivatives for the treatment of hepatitis c |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2013520507A JP2013520507A (ja) | 2013-06-06 |
| JP2013520507A5 true JP2013520507A5 (enExample) | 2014-04-10 |
Family
ID=43797530
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012555088A Ceased JP2013520507A (ja) | 2010-02-25 | 2011-02-23 | Ｃ型肝炎の処置のためのピラゾロピリダジン誘導体 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US8324212B2 (enExample) |
| EP (1) | EP2539340B1 (enExample) |
| JP (1) | JP2013520507A (enExample) |
| KR (1) | KR20130008570A (enExample) |
| CN (1) | CN102858777B (enExample) |
| AU (1) | AU2011220915A1 (enExample) |
| MX (1) | MX2012009759A (enExample) |
| WO (1) | WO2011106340A1 (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2010120671A (ru) * | 2007-10-24 | 2011-11-27 | Мерк Шарп Энд Домэ Корп. (Us) | Гетероциклические фениламидные антагонисты кальциевых каналов т-типа |
| 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 |
| 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 |
| US9303020B2 (en) | 2012-02-08 | 2016-04-05 | Bristol-Myers Squibb Company | Compounds for the treatment of hepatitis C |
Family Cites Families (20)
| 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 |
| US5917038A (en) | 1996-11-22 | 1999-06-29 | Eli Lilly And Company | Process of preparing substituted acrylamides |
| PE20020506A1 (es) | 2000-08-22 | 2002-07-09 | Glaxo Group Ltd | Derivados de pirazol fusionados como inhibidores de la proteina cinasa |
| JP2004525150A (ja) | 2001-03-30 | 2004-08-19 | スミスクライン ビーチャム コーポレーション | 治療用化合物としてのピラゾロピリジン類の使用 |
| WO2004041201A2 (en) | 2002-11-01 | 2004-05-21 | Viropharma Incorporated | Benzofuran compounds, compositions and methods for treatment and prophylaxis of hepatitis c viral infections and associated diseases |
| WO2005112640A2 (en) * | 2004-05-13 | 2005-12-01 | Viropharma Incorporated | 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 |
| BRPI0613962A2 (pt) * | 2005-07-25 | 2009-03-24 | Intermune Inc | inibidores macrocìclicos inovadores de replicação de vìrus da hepatite c |
| JP2009520735A (ja) * | 2005-12-22 | 2009-05-28 | スミスクライン・ビーチャム・コーポレイション | 抗ウイルス性２−カルボキシ−チオフェン化合物 |
| GB0707000D0 (en) | 2007-04-12 | 2007-05-30 | Istituto Di Ricerche D Biolog | Antiviral agents |
| EP2245023B1 (en) | 2008-02-14 | 2011-12-28 | F. Hoffmann-La Roche AG | Heterocyclic antiviral compounds |
| 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 |
| US8048887B2 (en) | 2008-09-11 | 2011-11-01 | 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 |
| US7994171B2 (en) | 2008-09-11 | 2011-08-09 | Bristol-Myers Squibb Company | Compounds for the treatment of hepatitis C |
| US20110031301A1 (en) | 2009-08-06 | 2011-02-10 | Segletes David S | Joining of Electrical Generator Components |
| AR080185A1 (es) | 2010-02-19 | 2012-03-21 | Glaxo Group Ltd | Derivados de acido boronico y benzofurano, composiciones farmaceuticas que los contienen,y uso de los mismos en el tratamiento y/o prevencion de infecciones virales, en particular por el virus de hepatitis c(hcv). |
| TW201136919A (en) | 2010-03-02 | 2011-11-01 | Merck Sharp & Amp Dohme Corp | Inhibitors of hepatitis C virus NS5B polymerase |
| WO2011106929A1 (en) | 2010-03-02 | 2011-09-09 | Merck Sharp & Dohme Corp. | Inhibitors of hepatitis c virus ns5b polymerase |
-
2011
- 2011-02-22 US US13/031,777 patent/US8324212B2/en active Active
- 2011-02-23 KR KR1020127024874A patent/KR20130008570A/ko not_active Withdrawn
- 2011-02-23 AU AU2011220915A patent/AU2011220915A1/en not_active Abandoned
- 2011-02-23 WO PCT/US2011/025803 patent/WO2011106340A1/en not_active Ceased
- 2011-02-23 JP JP2012555088A patent/JP2013520507A/ja not_active Ceased
- 2011-02-23 EP EP11706131.7A patent/EP2539340B1/en not_active Not-in-force
- 2011-02-23 CN CN201180020823.5A patent/CN102858777B/zh not_active Expired - Fee Related
- 2011-02-23 MX MX2012009759A patent/MX2012009759A/es active IP Right Grant
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