ZA200207845B - Macrocyclic NS3-serine protease inhibitors of hepatitis C virus comprising N-cyclic P2 moieties. - Google Patents
Macrocyclic NS3-serine protease inhibitors of hepatitis C virus comprising N-cyclic P2 moieties. Download PDFInfo
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- ZA200207845B ZA200207845B ZA200207845A ZA200207845A ZA200207845B ZA 200207845 B ZA200207845 B ZA 200207845B ZA 200207845 A ZA200207845 A ZA 200207845A ZA 200207845 A ZA200207845 A ZA 200207845A ZA 200207845 B ZA200207845 B ZA 200207845B
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- South Africa
- Prior art keywords
- alkyl
- aryl
- compound
- cha
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- 241000711549 Hepacivirus C Species 0.000 title description 32
- 239000003001 serine protease inhibitor Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 68
- -1 enantiomers Chemical class 0.000 claims description 64
- 125000000217 alkyl group Chemical group 0.000 claims description 42
- 238000000034 method Methods 0.000 claims description 25
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 23
- 125000003118 aryl group Chemical group 0.000 claims description 19
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 19
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- 125000001072 heteroaryl group Chemical group 0.000 claims description 15
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- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- 239000008194 pharmaceutical composition Substances 0.000 claims description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 12
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- 229940079322 interferon Drugs 0.000 claims description 10
- 238000011282 treatment Methods 0.000 claims description 10
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- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
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- 125000003545 alkoxy group Chemical group 0.000 claims description 6
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
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- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 4
- IWUCXVSUMQZMFG-AFCXAGJDSA-N Ribavirin Chemical group 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 description 4
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- 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 description 4
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- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 3
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
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- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 2
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- OOIBFPKQHULHSQ-UHFFFAOYSA-N (3-hydroxy-1-adamantyl) 2-methylprop-2-enoate Chemical compound C1C(C2)CC3CC2(O)CC1(OC(=O)C(=C)C)C3 OOIBFPKQHULHSQ-UHFFFAOYSA-N 0.000 claims 1
- 101100167365 Caenorhabditis elegans cha-1 gene Proteins 0.000 claims 1
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- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000001559 cyclopropyl group Chemical class [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
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- 125000005226 heteroaryloxycarbonyl group Chemical group 0.000 claims 1
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- MGQNMYSRDBFUIR-UHFFFAOYSA-N nitro cyanoformate Chemical compound [O-][N+](=O)OC(=O)C#N MGQNMYSRDBFUIR-UHFFFAOYSA-N 0.000 claims 1
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- RAHZWNYVWXNFOC-UHFFFAOYSA-N sulfur dioxide Inorganic materials O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
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- WYVKPHCYMTWUCW-YUPRTTJUSA-N Cys-Thr Chemical group C[C@@H]([C@@H](C(=O)O)NC(=O)[C@H](CS)N)O WYVKPHCYMTWUCW-YUPRTTJUSA-N 0.000 description 1
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- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06008—Dipeptides with the first amino acid being neutral
- C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/12—Cyclic peptides with only normal peptide bonds in the ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
- C07K1/02—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length in solution
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/08—Tripeptides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/08—Tripeptides
- C07K5/0802—Tripeptides with the first amino acid being neutral
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/08—Tripeptides
- C07K5/0802—Tripeptides with the first amino acid being neutral
- C07K5/0804—Tripeptides with the first amino acid being neutral and aliphatic
- C07K5/0806—Tripeptides with the first amino acid being neutral and aliphatic the side chain containing 0 or 1 carbon atoms, i.e. Gly, Ala
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/02—Linear peptides containing at least one abnormal peptide link
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US19460700P | 2000-04-05 | 2000-04-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200207845B true ZA200207845B (en) | 2004-02-11 |
Family
ID=22718227
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200207845A ZA200207845B (en) | 2000-04-05 | 2002-09-30 | Macrocyclic NS3-serine protease inhibitors of hepatitis C virus comprising N-cyclic P2 moieties. |
Country Status (26)
| Country | Link |
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| US (1) | US6846802B2 (es) |
| EP (1) | EP1268525B1 (es) |
| JP (1) | JP4748911B2 (es) |
| KR (1) | KR20030036152A (es) |
| CN (1) | CN1441806A (es) |
| AR (1) | AR029903A1 (es) |
| AT (1) | ATE419270T1 (es) |
| AU (1) | AU2001253124A1 (es) |
| BR (1) | BR0109861A (es) |
| CA (1) | CA2405521C (es) |
| CZ (1) | CZ20023321A3 (es) |
| DE (1) | DE60137207D1 (es) |
| EC (1) | ECSP014009A (es) |
| ES (1) | ES2317900T3 (es) |
| HK (1) | HK1047947A1 (es) |
| HU (1) | HUP0400456A3 (es) |
| IL (1) | IL151934A0 (es) |
| MX (1) | MXPA02009920A (es) |
| NO (1) | NO20024797L (es) |
| NZ (1) | NZ521455A (es) |
| PE (1) | PE20020188A1 (es) |
| PL (1) | PL359359A1 (es) |
| RU (1) | RU2002129564A (es) |
| SK (1) | SK14192002A3 (es) |
| WO (1) | WO2001077113A2 (es) |
| ZA (1) | ZA200207845B (es) |
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| CN1074422C (zh) | 1987-11-18 | 2001-11-07 | 希龙股份有限公司 | 制备含有hcv表位的分离多肽的方法 |
| DK0381216T3 (da) | 1989-02-01 | 1996-05-13 | Asahi Glass Co Ltd | Azeotrop eller azeotroplignende chlorfluorcarbonhydridblanding |
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| 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 |
| GB9812523D0 (en) * | 1998-06-10 | 1998-08-05 | Angeletti P Ist Richerche Bio | Peptide inhibitors of hepatitis c virus ns3 protease |
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| US6323180B1 (en) | 1998-08-10 | 2001-11-27 | Boehringer Ingelheim (Canada) Ltd | Hepatitis C inhibitor tri-peptides |
-
2001
- 2001-04-03 EP EP01926601A patent/EP1268525B1/en not_active Expired - Lifetime
- 2001-04-03 PL PL01359359A patent/PL359359A1/xx not_active Application Discontinuation
- 2001-04-03 KR KR1020027013276A patent/KR20030036152A/ko not_active Application Discontinuation
- 2001-04-03 AR ARP010101579A patent/AR029903A1/es unknown
- 2001-04-03 RU RU2002129564/04A patent/RU2002129564A/ru not_active Application Discontinuation
- 2001-04-03 US US09/825,399 patent/US6846802B2/en not_active Expired - Fee Related
- 2001-04-03 CA CA2405521A patent/CA2405521C/en not_active Expired - Fee Related
- 2001-04-03 ES ES01926601T patent/ES2317900T3/es not_active Expired - Lifetime
- 2001-04-03 BR BR0109861-6A patent/BR0109861A/pt not_active IP Right Cessation
- 2001-04-03 NZ NZ521455A patent/NZ521455A/en unknown
- 2001-04-03 WO PCT/US2001/010869 patent/WO2001077113A2/en active IP Right Grant
- 2001-04-03 IL IL15193401A patent/IL151934A0/xx unknown
- 2001-04-03 HU HU0400456A patent/HUP0400456A3/hu unknown
- 2001-04-03 MX MXPA02009920A patent/MXPA02009920A/es active IP Right Grant
- 2001-04-03 SK SK1419-2002A patent/SK14192002A3/sk unknown
- 2001-04-03 DE DE60137207T patent/DE60137207D1/de not_active Expired - Lifetime
- 2001-04-03 JP JP2001575586A patent/JP4748911B2/ja not_active Expired - Fee Related
- 2001-04-03 CN CN01810568A patent/CN1441806A/zh active Pending
- 2001-04-03 AU AU2001253124A patent/AU2001253124A1/en not_active Abandoned
- 2001-04-03 CZ CZ20023321A patent/CZ20023321A3/cs unknown
- 2001-04-03 AT AT01926601T patent/ATE419270T1/de not_active IP Right Cessation
- 2001-04-04 PE PE2001000316A patent/PE20020188A1/es not_active Application Discontinuation
- 2001-04-04 EC EC2001004009A patent/ECSP014009A/es unknown
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2002
- 2002-09-30 ZA ZA200207845A patent/ZA200207845B/en unknown
- 2002-10-04 NO NO20024797A patent/NO20024797L/no not_active Application Discontinuation
-
2003
- 2003-01-07 HK HK03100174.5A patent/HK1047947A1/zh unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ATE419270T1 (de) | 2009-01-15 |
| WO2001077113A3 (en) | 2002-06-20 |
| EP1268525A2 (en) | 2003-01-02 |
| US6846802B2 (en) | 2005-01-25 |
| IL151934A0 (en) | 2003-04-10 |
| US20020107181A1 (en) | 2002-08-08 |
| KR20030036152A (ko) | 2003-05-09 |
| CN1441806A (zh) | 2003-09-10 |
| HUP0400456A2 (hu) | 2004-06-28 |
| HK1047947A1 (zh) | 2003-03-14 |
| JP4748911B2 (ja) | 2011-08-17 |
| DE60137207D1 (de) | 2009-02-12 |
| AU2001253124A1 (en) | 2001-10-23 |
| CA2405521A1 (en) | 2001-10-18 |
| WO2001077113A2 (en) | 2001-10-18 |
| AR029903A1 (es) | 2003-07-23 |
| MXPA02009920A (es) | 2003-03-27 |
| ES2317900T3 (es) | 2009-05-01 |
| RU2002129564A (ru) | 2004-05-10 |
| JP2003530401A (ja) | 2003-10-14 |
| PE20020188A1 (es) | 2002-03-13 |
| BR0109861A (pt) | 2003-06-10 |
| CZ20023321A3 (cs) | 2003-01-15 |
| EP1268525B1 (en) | 2008-12-31 |
| ECSP014009A (es) | 2003-03-31 |
| NO20024797L (no) | 2002-12-04 |
| CA2405521C (en) | 2010-06-29 |
| HUP0400456A3 (en) | 2005-09-28 |
| NO20024797D0 (no) | 2002-10-04 |
| NZ521455A (en) | 2004-06-25 |
| PL359359A1 (en) | 2004-08-23 |
| SK14192002A3 (sk) | 2003-03-04 |
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