JP2005535574A5 - - Google Patents
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- JP2005535574A5 JP2005535574A5 JP2003584048A JP2003584048A JP2005535574A5 JP 2005535574 A5 JP2005535574 A5 JP 2005535574A5 JP 2003584048 A JP2003584048 A JP 2003584048A JP 2003584048 A JP2003584048 A JP 2003584048A JP 2005535574 A5 JP2005535574 A5 JP 2005535574A5
- Authority
- JP
- Japan
- Prior art keywords
- aliphatic
- compound
- ring
- aryl
- cycloalkyl
- 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.)
- Pending
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- 150000001875 compounds Chemical class 0.000 claims 113
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 41
- 125000001424 substituent group Chemical group 0.000 claims 38
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims 36
- 229910052757 nitrogen Inorganic materials 0.000 claims 36
- 229910052760 oxygen Inorganic materials 0.000 claims 35
- 229910052717 sulfur Inorganic materials 0.000 claims 34
- 125000005842 heteroatoms Chemical group 0.000 claims 32
- 125000006714 (C3-C10) heterocyclyl group Chemical group 0.000 claims 31
- 125000003118 aryl group Chemical group 0.000 claims 24
- 125000000623 heterocyclic group Chemical group 0.000 claims 24
- -1 1,2-methylenedioxy Chemical group 0.000 claims 18
- 125000001072 heteroaryl group Chemical group 0.000 claims 18
- 229910052739 hydrogen Inorganic materials 0.000 claims 18
- 239000001257 hydrogen Substances 0.000 claims 18
- 125000001931 aliphatic group Chemical group 0.000 claims 17
- 125000006717 (C3-C10) cycloalkenyl group Chemical group 0.000 claims 16
- 239000000203 mixture Substances 0.000 claims 15
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 14
- 125000004429 atoms Chemical group 0.000 claims 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 14
- 125000004122 cyclic group Chemical group 0.000 claims 12
- 125000002619 bicyclic group Chemical group 0.000 claims 11
- 229910052736 halogen Inorganic materials 0.000 claims 11
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 10
- 230000002401 inhibitory effect Effects 0.000 claims 9
- 150000002829 nitrogen Chemical group 0.000 claims 9
- 125000005843 halogen group Chemical group 0.000 claims 8
- 239000003112 inhibitor Substances 0.000 claims 8
- 125000002950 monocyclic group Chemical group 0.000 claims 7
- 229920000728 polyester Polymers 0.000 claims 7
- 201000002674 obstructive nephropathy Diseases 0.000 claims 6
- 125000004043 oxo group Chemical group O=* 0.000 claims 6
- 125000000165 tricyclic carbocycle group Chemical group 0.000 claims 6
- 125000006721 (C5-C10) heteroaryl (C1-C6) alkyl group Chemical group 0.000 claims 5
- 125000006719 (C6-C10) aryl (C1-C6) alkyl group Chemical group 0.000 claims 5
- 239000003795 chemical substances by application Substances 0.000 claims 5
- 150000002367 halogens Chemical class 0.000 claims 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- 102000033147 ERVK-25 Human genes 0.000 claims 4
- 108091005771 Peptidases Proteins 0.000 claims 4
- 239000004365 Protease Substances 0.000 claims 4
- 239000003443 antiviral agent Substances 0.000 claims 4
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims 4
- 229910052796 boron Inorganic materials 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 4
- 125000004432 carbon atoms Chemical group C* 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- 125000006574 non-aromatic ring group Chemical group 0.000 claims 4
- 125000003396 thiol group Chemical group [H]S* 0.000 claims 4
- 125000000464 thioxo group Chemical group S=* 0.000 claims 4
- 210000001124 Body Fluids Anatomy 0.000 claims 3
- 102000012479 Serine Proteases Human genes 0.000 claims 3
- 108010022999 Serine Proteases Proteins 0.000 claims 3
- IQFYYKKMVGJFEH-CSMHCCOUSA-N Telbivudine Chemical compound O=C1NC(=O)C(C)=CN1[C@H]1O[C@@H](CO)[C@H](O)C1 IQFYYKKMVGJFEH-CSMHCCOUSA-N 0.000 claims 3
- 150000002431 hydrogen Chemical class 0.000 claims 3
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims 3
- 229960005311 telbivudine Drugs 0.000 claims 3
- 101710036216 ATEG_03556 Proteins 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
- 210000004369 Blood Anatomy 0.000 claims 2
- 102000003996 Interferon beta Human genes 0.000 claims 2
- 108090000467 Interferon beta Proteins 0.000 claims 2
- 102000005741 Metalloproteases Human genes 0.000 claims 2
- 108010006035 Metalloproteases Proteins 0.000 claims 2
- 101710003000 ORF1/ORF2 Proteins 0.000 claims 2
- 101700030467 Pol Proteins 0.000 claims 2
- 102000007501 Thymosin Human genes 0.000 claims 2
- 108010046075 Thymosin Proteins 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 239000012472 biological sample Substances 0.000 claims 2
- 239000008280 blood Substances 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 230000002519 immonomodulatory Effects 0.000 claims 2
- 239000002955 immunomodulating agent Substances 0.000 claims 2
- 230000002584 immunomodulator Effects 0.000 claims 2
- 229940121354 immunomodulators Drugs 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 101710004466 rgy Proteins 0.000 claims 2
- 101710030364 rgy1 Proteins 0.000 claims 2
- 101710030359 rgy2 Proteins 0.000 claims 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- 241000790917 Dioxys <bee> Species 0.000 claims 1
- 102000008070 Interferon-gamma Human genes 0.000 claims 1
- 108010074328 Interferon-gamma Proteins 0.000 claims 1
- 102000014150 Interferons Human genes 0.000 claims 1
- 108010050904 Interferons Proteins 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 230000000240 adjuvant Effects 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
- 239000010839 body fluid Substances 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 238000011109 contamination Methods 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 201000009910 diseases by infectious agent Diseases 0.000 claims 1
- 239000002552 dosage form Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 229940044627 gamma-interferon Drugs 0.000 claims 1
- 229940079322 interferon Drugs 0.000 claims 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 1
- OAICVXFJPJFONN-UHFFFAOYSA-N phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 1
- 229910052698 phosphorus Inorganic materials 0.000 claims 1
- 239000011574 phosphorus Substances 0.000 claims 1
- 239000000651 prodrug Substances 0.000 claims 1
- 229940002612 prodrugs Drugs 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000000523 sample Substances 0.000 claims 1
- 239000011780 sodium chloride Substances 0.000 claims 1
- 239000011232 storage material Substances 0.000 claims 1
- 210000001519 tissues Anatomy 0.000 claims 1
- 0 CC(*)C(C)C1CCCC1 Chemical compound CC(*)C(C)C1CCCC1 0.000 description 17
- GDBCVIHZQYAWLU-UHFFFAOYSA-N CC(C(CCC1CC23N(C)CCC2)N1C3=O)=O Chemical compound CC(C(CCC1CC23N(C)CCC2)N1C3=O)=O GDBCVIHZQYAWLU-UHFFFAOYSA-N 0.000 description 1
- VTOITISQJGMVSQ-UHFFFAOYSA-N CC(C(CCC1CCCC2NC)N1C2=O)=O Chemical compound CC(C(CCC1CCCC2NC)N1C2=O)=O VTOITISQJGMVSQ-UHFFFAOYSA-N 0.000 description 1
- TUFWJBPCWWPJJX-UHFFFAOYSA-N CC(C(CCC1NCC2NC)N1C2=O)=O Chemical compound CC(C(CCC1NCC2NC)N1C2=O)=O TUFWJBPCWWPJJX-UHFFFAOYSA-N 0.000 description 1
- HJNGFPBZCZRPJX-UHFFFAOYSA-N CC(C(CCC1NCCC2NC)N1C2=O)=O Chemical compound CC(C(CCC1NCCC2NC)N1C2=O)=O HJNGFPBZCZRPJX-UHFFFAOYSA-N 0.000 description 1
- JCIZAGNGBHWOES-UHFFFAOYSA-N CC(C(CCC1SCC2NC)N1C2=O)=O Chemical compound CC(C(CCC1SCC2NC)N1C2=O)=O JCIZAGNGBHWOES-UHFFFAOYSA-N 0.000 description 1
- RECBQSVGWIRVQV-UHFFFAOYSA-N CC(C(CCC1SCCC2NC)N1C2=O)=O Chemical compound CC(C(CCC1SCCC2NC)N1C2=O)=O RECBQSVGWIRVQV-UHFFFAOYSA-N 0.000 description 1
- QFXDFUFPSSTROV-UHFFFAOYSA-N CC(C(CCCC1CC23N(C)CCC2)N1C3=O)=O Chemical compound CC(C(CCCC1CC23N(C)CCC2)N1C3=O)=O QFXDFUFPSSTROV-UHFFFAOYSA-N 0.000 description 1
- ZXJCQACFSYGMPO-UHFFFAOYSA-N CC(C(CCSC1CC23N(C)CCC2)N1C3=[U])=O Chemical compound CC(C(CCSC1CC23N(C)CCC2)N1C3=[U])=O ZXJCQACFSYGMPO-UHFFFAOYSA-N 0.000 description 1
- RXSWFHPGDPYGRL-IDKOKCKLSA-N CC(C(CC[C@@H]1CCC2NC)N1C2=O)=O Chemical compound CC(C(CC[C@@H]1CCC2NC)N1C2=O)=O RXSWFHPGDPYGRL-IDKOKCKLSA-N 0.000 description 1
- NQIMYAPMJDMGFM-UHFFFAOYSA-N CC(C(CSC1CC23N(C)CCC2)N1C3=O)=O Chemical compound CC(C(CSC1CC23N(C)CCC2)N1C3=O)=O NQIMYAPMJDMGFM-UHFFFAOYSA-N 0.000 description 1
- DVGMAZIZBADOBU-UHFFFAOYSA-N CC(C)(CC(C)=O)CNC Chemical compound CC(C)(CC(C)=O)CNC DVGMAZIZBADOBU-UHFFFAOYSA-N 0.000 description 1
- XQIUXEOBOCSGFV-UHFFFAOYSA-N CC1=CC=CCC1C[Sc](C)C Chemical compound CC1=CC=CCC1C[Sc](C)C XQIUXEOBOCSGFV-UHFFFAOYSA-N 0.000 description 1
- QVVPJFZQUZTCKD-UHFFFAOYSA-O CCC(C)C(C(C(NC(C)CC)=N)=O)NC(C(C)(CC1C2CCCC1)N2C(C(C)(C(C)(C)C)NC(C(C1CCCCC1)NC(C([NH3+])=CC=N)=O)=O)=O)=O Chemical compound CCC(C)C(C(C(NC(C)CC)=N)=O)NC(C(C)(CC1C2CCCC1)N2C(C(C)(C(C)(C)C)NC(C(C1CCCCC1)NC(C([NH3+])=CC=N)=O)=O)=O)=O QVVPJFZQUZTCKD-UHFFFAOYSA-O 0.000 description 1
- SUNIXXUMZRROKD-OWDBQKORSA-N CCC(C1)[C@]1(C(C(NC1C=C1)=O)=O)NC([C@](C1)(C1C(CCC1)C2C1C(C)(C)[C@@H]1NC([C@H](C3CCCCC3)NC(c3nccnc3)=O)=O)N2C1=O)=O Chemical compound CCC(C1)[C@]1(C(C(NC1C=C1)=O)=O)NC([C@](C1)(C1C(CCC1)C2C1C(C)(C)[C@@H]1NC([C@H](C3CCCCC3)NC(c3nccnc3)=O)=O)N2C1=O)=O SUNIXXUMZRROKD-OWDBQKORSA-N 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US37184602P | 2002-04-11 | 2002-04-11 | |
| PCT/US2003/011459 WO2003087092A2 (en) | 2002-04-11 | 2003-04-11 | Inhibitors of serine proteases, particularly hepatitis c virus ns3 - ns4 protease |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009128587A Division JP2009185081A (ja) | 2002-04-11 | 2009-05-28 | セリンプロテアーゼ、特にｈｃｖｎｓ３−ｎｓ４ａプロテアーゼのインヒビター |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2005535574A JP2005535574A (ja) | 2005-11-24 |
| JP2005535574A5 true JP2005535574A5 (US08039623-20111018-C00020.png) | 2006-06-01 |
Family
ID=29250748
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003584048A Pending JP2005535574A (ja) | 2002-04-11 | 2003-04-11 | セリンプロテアーゼ、特にｈｃｖｎｓ３−ｎｓ４ａプロテアーゼのインヒビター |
| JP2009128587A Pending JP2009185081A (ja) | 2002-04-11 | 2009-05-28 | セリンプロテアーゼ、特にｈｃｖｎｓ３−ｎｓ４ａプロテアーゼのインヒビター |
| JP2010151000A Pending JP2010241821A (ja) | 2002-04-11 | 2010-07-01 | セリンプロテアーゼ、特にｈｃｖｎｓ３−ｎｓ４ａプロテアーゼのインヒビター |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009128587A Pending JP2009185081A (ja) | 2002-04-11 | 2009-05-28 | セリンプロテアーゼ、特にｈｃｖｎｓ３−ｎｓ４ａプロテアーゼのインヒビター |
| JP2010151000A Pending JP2010241821A (ja) | 2002-04-11 | 2010-07-01 | セリンプロテアーゼ、特にｈｃｖｎｓ３−ｎｓ４ａプロテアーゼのインヒビター |
Country Status (18)
Families Citing this family (120)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL194025B1 (pl) * | 1996-10-18 | 2007-04-30 | Vertex Pharma | Inhibitory proteaz serynowych, a zwłaszcza proteazy wirusa NS3 zapalenia wątroby C, kompozycja farmaceutyczna i zastosowanie inhibitorów proteaz serynowych |
| AU2001251165A1 (en) * | 2000-04-03 | 2001-10-15 | Vertex Pharmaceuticals Incorporated | Inhibitors of serine proteases, particularly hepatitis c virus ns3 protease |
| SV2003000617A (es) | 2000-08-31 | 2003-01-13 | Lilly Co Eli | Inhibidores de la proteasa peptidomimetica ref. x-14912m |
| AU2002348414B2 (en) * | 2001-10-24 | 2009-10-01 | Vertex Pharmaceuticals Incorporated | Inhibitors of serine protease, particularly hepatitis C virus NS3-NS4A protease, incorporating a fused ring system |
| SG159385A1 (en) * | 2002-04-11 | 2010-03-30 | Vertex Pharma | Inhibitors of serine proteases, particularly hepatitis c virus ns3 - ns4 protease |
| CN100453553C (zh) | 2003-04-11 | 2009-01-21 | 沃泰克斯药物股份有限公司 | 丝氨酸蛋白酶、特别是hcv ns3-ns4a蛋白酶的抑制剂 |
| AU2011203054B2 (en) * | 2003-04-11 | 2012-04-26 | Vertex Pharmaceuticals, Incorporated | Inhibitors of Serine Proteases, Particularly HCV NS3-NS4A Protease |
| TW200510391A (en) * | 2003-04-11 | 2005-03-16 | Vertex Pharma | Inhibitors of serine proteases, particularly HCV NS3-NS4A protease |
| EP1646642A2 (en) * | 2003-07-18 | 2006-04-19 | Vertex Pharmaceuticals Incorporated | Inhibitors of serine proteases, particularly hcv ns3-ns4a protease |
| MY148123A (en) * | 2003-09-05 | 2013-02-28 | Vertex Pharma | Inhibitors of serine proteases, particularly hcv ns3-ns4a protease |
| JP4685775B2 (ja) | 2003-09-18 | 2011-05-18 | バーテックス ファーマシューティカルズ インコーポレイテッド | セリンプロテアーゼ、とりわけｈｃｖｎｓ３−ｎｓ４ａプロテアーゼの阻害剤 |
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| JP4942485B2 (ja) | 2003-10-28 | 2012-05-30 | バーテックス ファーマシューティカルズ インコーポレイテッド | Ｆｉｓｃｈｅｒ−ｆｉｎｋ型合成および続くアシル化による４，５−ジアルキル−３−アシル−ピロール−２−カルボン酸誘導体の製造 |
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| US7781478B2 (en) | 2004-07-14 | 2010-08-24 | Ptc Therapeutics, Inc. | Methods for treating hepatitis C |
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| UA100669C2 (ru) * | 2006-06-01 | 2013-01-25 | Санофі-Авентіс | Спироциклические нитрилы как ингибиторы протеазы, способ их получения (варианты) и лекарственное средство на их основе |
| RU2008152171A (ru) * | 2006-07-05 | 2010-08-10 | Интермьюн, Инк. (Us) | Новые ингибиторы вирусной репликации гепатита с |
| JP5290186B2 (ja) | 2006-11-15 | 2013-09-18 | ヴァイロケム ファーマ インコーポレイテッド | フラビウイルス感染症の治療または予防用のチオフェン類似体 |
| TWI406660B (zh) | 2006-11-17 | 2013-09-01 | Tibotec Pharm Ltd | Ｃ型肝炎病毒之巨環抑制劑 |
| AP2009004960A0 (en) * | 2007-02-27 | 2009-08-31 | Vertex Pharma | Co-crystals and pharmaceutical compositions comprising the same |
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- 2003-04-11 KR KR1020117004808A patent/KR20110028665A/ko not_active Application Discontinuation
- 2003-04-11 CN CNB03809665XA patent/CN100381440C/zh not_active Expired - Fee Related
- 2003-04-11 CA CA2481369A patent/CA2481369C/en not_active Expired - Fee Related
- 2003-04-11 EP EP12160782A patent/EP2468744A2/en not_active Withdrawn
- 2003-04-11 NZ NZ561851A patent/NZ561851A/en not_active IP Right Cessation
- 2003-04-11 RU RU2004133044/04A patent/RU2004133044A/ru not_active Application Discontinuation
- 2003-04-11 US US10/412,600 patent/US7273885B2/en not_active Expired - Fee Related
- 2003-04-11 CN CNA2008100823499A patent/CN101245097A/zh active Pending
- 2003-04-11 TW TW092108412A patent/TW200403236A/zh unknown
- 2003-04-11 AU AU2003223602A patent/AU2003223602B8/en not_active Ceased
- 2003-04-11 PL PL03373399A patent/PL373399A1/xx not_active Application Discontinuation
- 2003-04-11 MX MXPA04009938A patent/MXPA04009938A/es active IP Right Grant
- 2003-04-11 EP EP03719741A patent/EP1497282A2/en not_active Withdrawn
- 2003-04-11 KR KR10-2004-7016168A patent/KR20040099425A/ko not_active Application Discontinuation
- 2003-04-11 WO PCT/US2003/011459 patent/WO2003087092A2/en active Application Filing
- 2003-04-11 NZ NZ575692A patent/NZ575692A/en not_active IP Right Cessation
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2004
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- 2004-11-10 NO NO20044889A patent/NO20044889L/no unknown
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2006
- 2006-01-27 HK HK06101291A patent/HK1081196A1/xx not_active IP Right Cessation
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2007
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2009
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- 2009-06-03 US US12/477,581 patent/US20100173851A1/en not_active Abandoned
- 2009-10-30 AU AU2009233604A patent/AU2009233604A1/en not_active Abandoned
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2010
- 2010-07-01 JP JP2010151000A patent/JP2010241821A/ja active Pending
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2011
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