JP2010510234A5 - - Google Patents
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- Publication number
- JP2010510234A5 JP2010510234A5 JP2009537359A JP2009537359A JP2010510234A5 JP 2010510234 A5 JP2010510234 A5 JP 2010510234A5 JP 2009537359 A JP2009537359 A JP 2009537359A JP 2009537359 A JP2009537359 A JP 2009537359A JP 2010510234 A5 JP2010510234 A5 JP 2010510234A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- cycloalkyl
- hcv
- aryl
- arylalkyl
- 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
- 125000000217 alkyl group Chemical group 0.000 claims 48
- 125000000753 cycloalkyl group Chemical group 0.000 claims 31
- 125000003118 aryl group Chemical group 0.000 claims 19
- 125000003710 aryl alkyl group Chemical group 0.000 claims 18
- 150000001875 compounds Chemical class 0.000 claims 16
- 125000001188 haloalkyl group Chemical group 0.000 claims 15
- 125000000623 heterocyclic group Chemical group 0.000 claims 14
- 239000001257 hydrogen Substances 0.000 claims 14
- 229910052739 hydrogen Inorganic materials 0.000 claims 14
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 12
- 125000003342 alkenyl group Chemical group 0.000 claims 9
- 125000003545 alkoxy group Chemical group 0.000 claims 9
- 150000003839 salts Chemical class 0.000 claims 9
- 108010050904 Interferons Proteins 0.000 claims 8
- 102000014150 Interferons Human genes 0.000 claims 8
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 8
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 8
- 229940079322 interferon Drugs 0.000 claims 8
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 7
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 7
- 239000003814 drug Substances 0.000 claims 7
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 7
- 229940124597 therapeutic agent Drugs 0.000 claims 7
- 125000004994 halo alkoxy alkyl group Chemical group 0.000 claims 6
- 229910052757 nitrogen Inorganic materials 0.000 claims 6
- 125000005843 halogen group Chemical group 0.000 claims 5
- 125000001424 substituent group Chemical group 0.000 claims 5
- 108010047761 Interferon-alpha Proteins 0.000 claims 4
- 102000006992 Interferon-alpha Human genes 0.000 claims 4
- 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 4
- 125000004966 cyanoalkyl group Chemical group 0.000 claims 4
- 125000005842 heteroatom Chemical group 0.000 claims 4
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 4
- 229960000329 ribavirin Drugs 0.000 claims 4
- 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 4
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 4
- 125000005170 cycloalkyloxycarbonyl group Chemical group 0.000 claims 3
- 125000004993 haloalkoxycarbonyl group Chemical group 0.000 claims 3
- 208000015181 infectious disease Diseases 0.000 claims 3
- 108091032973 (ribonucleotides)n+m Proteins 0.000 claims 2
- UBCHPRBFMUDMNC-UHFFFAOYSA-N 1-(1-adamantyl)ethanamine Chemical compound C1C(C2)CC3CC2CC1(C(N)C)C3 UBCHPRBFMUDMNC-UHFFFAOYSA-N 0.000 claims 2
- 108020005544 Antisense RNA Proteins 0.000 claims 2
- 229940124186 Dehydrogenase inhibitor Drugs 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- HAEJPQIATWHALX-KQYNXXCUSA-N ITP Chemical compound O[C@@H]1[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)O[C@H]1N1C(N=CNC2=O)=C2N=C1 HAEJPQIATWHALX-KQYNXXCUSA-N 0.000 claims 2
- 101710200424 Inosine-5'-monophosphate dehydrogenase Proteins 0.000 claims 2
- 102100040018 Interferon alpha-2 Human genes 0.000 claims 2
- 108010079944 Interferon-alpha2b Proteins 0.000 claims 2
- 102000013462 Interleukin-12 Human genes 0.000 claims 2
- 108010065805 Interleukin-12 Proteins 0.000 claims 2
- 102000000588 Interleukin-2 Human genes 0.000 claims 2
- 108010002350 Interleukin-2 Proteins 0.000 claims 2
- 102000004889 Interleukin-6 Human genes 0.000 claims 2
- 108090001005 Interleukin-6 Proteins 0.000 claims 2
- 102000005741 Metalloproteases Human genes 0.000 claims 2
- 108010006035 Metalloproteases Proteins 0.000 claims 2
- 108060004795 Methyltransferase Proteins 0.000 claims 2
- 101800001019 Non-structural protein 4B Proteins 0.000 claims 2
- 101800001014 Non-structural protein 5A Proteins 0.000 claims 2
- 229910019142 PO4 Inorganic materials 0.000 claims 2
- 102000012479 Serine Proteases Human genes 0.000 claims 2
- 108010022999 Serine Proteases Proteins 0.000 claims 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
- 230000005867 T cell response Effects 0.000 claims 2
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 2
- 125000004414 alkyl thio group Chemical group 0.000 claims 2
- DKNWSYNQZKUICI-UHFFFAOYSA-N amantadine Chemical compound C1C(C2)CC3CC2CC1(N)C3 DKNWSYNQZKUICI-UHFFFAOYSA-N 0.000 claims 2
- 229960003805 amantadine Drugs 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 125000005243 carbonyl alkyl group Chemical group 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 125000004181 carboxyalkyl group Chemical group 0.000 claims 2
- 239000003184 complementary RNA Substances 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 2
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims 2
- 125000004438 haloalkoxy group Chemical group 0.000 claims 2
- 125000004692 haloalkylcarbonyl group Chemical group 0.000 claims 2
- 210000002443 helper t lymphocyte Anatomy 0.000 claims 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 2
- 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 2
- 229960002751 imiquimod Drugs 0.000 claims 2
- 230000002452 interceptive effect Effects 0.000 claims 2
- 229940117681 interleukin-12 Drugs 0.000 claims 2
- 229940100601 interleukin-6 Drugs 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- 239000001301 oxygen Chemical group 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 2
- 239000010452 phosphate Substances 0.000 claims 2
- 229960000888 rimantadine Drugs 0.000 claims 2
- 229910052717 sulfur Chemical group 0.000 claims 2
- 239000011593 sulfur Chemical group 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US86613006P | 2006-11-16 | 2006-11-16 | |
| US60/866,130 | 2006-11-16 | ||
| US11/939,780 | 2007-11-14 | ||
| US11/939,780 US7888464B2 (en) | 2006-11-16 | 2007-11-14 | Hepatitis C virus inhibitors |
| PCT/US2007/084799 WO2008064066A1 (en) | 2006-11-16 | 2007-11-15 | Hepatitis c virus inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2010510234A JP2010510234A (ja) | 2010-04-02 |
| JP2010510234A5 true JP2010510234A5 (enExample) | 2010-12-24 |
| JP5241729B2 JP5241729B2 (ja) | 2013-07-17 |
Family
ID=39247306
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009537359A Expired - Fee Related JP5241729B2 (ja) | 2006-11-16 | 2007-11-15 | Ｃ型肝炎ウイルス阻害剤 |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US7888464B2 (enExample) |
| EP (1) | EP2086995B1 (enExample) |
| JP (1) | JP5241729B2 (enExample) |
| KR (1) | KR20090083462A (enExample) |
| AT (1) | ATE546460T1 (enExample) |
| AU (1) | AU2007323793A1 (enExample) |
| BR (1) | BRPI0719008A2 (enExample) |
| CA (1) | CA2669856A1 (enExample) |
| CO (1) | CO6190510A2 (enExample) |
| EA (1) | EA015827B1 (enExample) |
| ES (1) | ES2381308T3 (enExample) |
| IL (1) | IL198741A0 (enExample) |
| MX (1) | MX2009004943A (enExample) |
| NO (1) | NO20091871L (enExample) |
| NZ (1) | NZ576814A (enExample) |
| WO (1) | WO2008064066A1 (enExample) |
Families Citing this family (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MY140680A (en) | 2002-05-20 | 2010-01-15 | Bristol Myers Squibb Co | Hepatitis c virus inhibitors |
| US20100087382A1 (en) * | 2007-02-16 | 2010-04-08 | Boehringer Ingelheim International Gmbh | Inhibitors of Hepatitis C NS3 Protease |
| US8183408B2 (en) | 2007-11-16 | 2012-05-22 | Kaneka Corporation | Process for production of N-carbamoyl-tert-leucine |
| US8940688B2 (en) * | 2007-12-05 | 2015-01-27 | Enanta Pharmaceuticals, Inc. | Fluorinated tripeptide HCV serine protease inhibitors |
| MX2010008109A (es) * | 2008-01-24 | 2010-09-22 | Enanta Pharm Inc | Tripéptidos difluorizados como inhibidores de proteasa de serina de virus de hepatitis c (hcv). |
| WO2009117594A1 (en) * | 2008-03-20 | 2009-09-24 | Enanta Pharmaceuticals, Inc. | Fluorinated macrocyclic compounds as hepatitis c virus inhibitors |
| US8207341B2 (en) | 2008-09-04 | 2012-06-26 | Bristol-Myers Squibb Company | Process or synthesizing substituted isoquinolines |
| UY32099A (es) | 2008-09-11 | 2010-04-30 | Enanta Pharm Inc | Inhibidores macrocíclicos de serina proteasas de hepatitis c |
| US8563505B2 (en) * | 2008-09-29 | 2013-10-22 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US8044087B2 (en) * | 2008-09-29 | 2011-10-25 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US20100272674A1 (en) * | 2008-12-04 | 2010-10-28 | Bristol-Myers Squibb Company | Hepatitis C Virus Inhibitors |
| US8283310B2 (en) * | 2008-12-15 | 2012-10-09 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| TW201040181A (en) | 2009-04-08 | 2010-11-16 | Idenix Pharmaceuticals Inc | Macrocyclic serine protease inhibitors |
| US8512690B2 (en) | 2009-04-10 | 2013-08-20 | Novartis Ag | Derivatised proline containing peptide compounds as protease inhibitors |
| JP2012532146A (ja) * | 2009-07-02 | 2012-12-13 | ドクター・レディーズ・ラボラトリーズ・リミテッド | アミノビニルシクロプロパンカルボン酸誘導体の分割のための酵素および方法 |
| CA2769652A1 (en) | 2009-08-05 | 2011-02-10 | Idenix Pharmaceuticals, Inc. | Macrocyclic serine protease inhibitors useful against viral infections, particularly hcv |
| WO2012039132A1 (ja) * | 2010-09-22 | 2012-03-29 | 三井化学アグロ株式会社 | 含フッ素カルバマート基を有するアミノ酸アミド誘導体の製造方法、その製造中間体、及びエチレンジアミン誘導体の製造方法 |
| JP5918264B2 (ja) | 2010-12-22 | 2016-05-18 | アッヴィ・インコーポレイテッド | Ｃ型肝炎阻害剤およびその使用 |
| CA2822556A1 (en) | 2010-12-30 | 2012-07-05 | Enanta Pharmaceuticals, Inc | Macrocyclic hepatitis c serine protease inhibitors |
| CN103380132B (zh) | 2010-12-30 | 2016-08-31 | 益安药业 | 菲啶大环丙型肝炎丝氨酸蛋白酶抑制剂 |
| TW201309690A (zh) | 2011-02-10 | 2013-03-01 | Idenix Pharmaceuticals Inc | 巨環絲胺酸蛋白酶抑制劑，其醫藥組合物及其於治療ｈｃｖ感染之用途 |
| US8957203B2 (en) | 2011-05-05 | 2015-02-17 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US10201584B1 (en) | 2011-05-17 | 2019-02-12 | Abbvie Inc. | Compositions and methods for treating HCV |
| US8691757B2 (en) | 2011-06-15 | 2014-04-08 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| WO2013030750A1 (en) | 2011-09-01 | 2013-03-07 | Lupin Limited | Antiviral compounds |
| US9073943B2 (en) | 2012-02-10 | 2015-07-07 | Lupin Limited | Antiviral compounds with a dibenzooxaheterocycle moiety |
| WO2013190509A2 (en) * | 2012-06-22 | 2013-12-27 | Dr.Reddys Laboratories Limited | Preparation of intermediates of boceprevir |
| UA119315C2 (uk) | 2012-07-03 | 2019-06-10 | Гіліад Фармассет Елелсі | Інгібітори вірусу гепатиту с |
| SI2909205T1 (sl) | 2012-10-19 | 2017-02-28 | Bristol-Myers Squibb Company | 9-metil substituiran heksadekahidrociklopropa(e)pirolo(1,2-A)(1,4)diazaciklopentadecinil karbamat derivati kot nestrukturalni 3 (NS3) proteazni inhibitorji za zdravljenje hepatitis C virusnih infekcij |
| EP2914598B1 (en) | 2012-11-02 | 2017-10-18 | Bristol-Myers Squibb Company | Hepatitis c virus inhibitors |
| US9643999B2 (en) | 2012-11-02 | 2017-05-09 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| WO2014070964A1 (en) | 2012-11-02 | 2014-05-08 | Bristol-Myers Squibb Company | Hepatitis c virus inhibitors |
| US9409943B2 (en) | 2012-11-05 | 2016-08-09 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| JP6342922B2 (ja) | 2013-03-07 | 2018-06-13 | ブリストル−マイヤーズ スクイブ カンパニーＢｒｉｓｔｏｌ−Ｍｙｅｒｓ Ｓｑｕｉｂｂ Ｃｏｍｐａｎｙ | Ｃ型肝炎ウイルス阻害剤 |
| BR112015021768A2 (pt) | 2013-03-15 | 2016-02-02 | Gilead Sciences Inc | inibidores do vírus da hepatite c |
| CN103396344B (zh) * | 2013-08-08 | 2014-10-29 | 苏州永健生物医药有限公司 | 一锅法合成n-叔丁氨羰基-3-甲基-l-缬氨酸的方法 |
| EP3089757A1 (en) | 2014-01-03 | 2016-11-09 | AbbVie Inc. | Solid antiviral dosage forms |
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| EP0475255A3 (en) | 1990-09-12 | 1993-04-14 | F. Hoffmann-La Roche Ag | Process for the preparation of optically pure (s)-alpha-((tert-butylsulfonyl)methyl)hydro cinnamic acid |
| DE69709671T2 (de) | 1996-10-18 | 2002-08-22 | Vertex Pharmaceuticals Inc., Cambridge | Inhibitoren von serinproteasen, insbesondere von ns3-protease des hepatitis-c-virus |
| JP4452401B2 (ja) | 1997-08-11 | 2010-04-21 | ベーリンガー インゲルハイム （カナダ） リミテッド | Ｃ型肝炎ウイルス阻害ペプチドアナログ |
| EP1003775B1 (en) | 1997-08-11 | 2005-03-16 | Boehringer Ingelheim (Canada) Ltd. | Hepatitis c inhibitor peptides |
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| US20060199773A1 (en) | 2002-05-20 | 2006-09-07 | Sausker Justin B | Crystalline forms of (1R,2S)-N-[(1,1-dimethylethoxy)carbonyl]-3-methyl-L-valyl-(4R)-4-[(6-methoxy-1-isoquinolinyl)oxy]-L-prolyl-1-amino-N-(cyclopropylsulfonyl)-2-ethenyl-cyclopropanecarboxamide, monopotassium salt |
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| PL215228B1 (pl) | 2002-05-20 | 2013-11-29 | Bristol Myers Squibb Co | Zwiazki tripeptydowe, ich zastosowanie i kompozycja farmaceutyczna je zawierajaca oraz jej zastosowanie |
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2007
- 2007-11-14 US US11/939,780 patent/US7888464B2/en active Active
- 2007-11-15 KR KR1020097012336A patent/KR20090083462A/ko not_active Withdrawn
- 2007-11-15 CA CA002669856A patent/CA2669856A1/en not_active Abandoned
- 2007-11-15 BR BRPI0719008-5A2A patent/BRPI0719008A2/pt not_active IP Right Cessation
- 2007-11-15 NZ NZ576814A patent/NZ576814A/en not_active IP Right Cessation
- 2007-11-15 MX MX2009004943A patent/MX2009004943A/es active IP Right Grant
- 2007-11-15 WO PCT/US2007/084799 patent/WO2008064066A1/en not_active Ceased
- 2007-11-15 JP JP2009537359A patent/JP5241729B2/ja not_active Expired - Fee Related
- 2007-11-15 AT AT07864446T patent/ATE546460T1/de active
- 2007-11-15 AU AU2007323793A patent/AU2007323793A1/en not_active Abandoned
- 2007-11-15 EP EP07864446A patent/EP2086995B1/en active Active
- 2007-11-15 EA EA200900697A patent/EA015827B1/ru not_active IP Right Cessation
- 2007-11-15 ES ES07864446T patent/ES2381308T3/es active Active
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2009
- 2009-05-13 NO NO20091871A patent/NO20091871L/no not_active Application Discontinuation
- 2009-05-14 IL IL198741A patent/IL198741A0/en unknown
- 2009-05-15 CO CO09049882A patent/CO6190510A2/es not_active Application Discontinuation