JP2007505031A5 - - Google Patents
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- Publication number
- JP2007505031A5 JP2007505031A5 JP2006517916A JP2006517916A JP2007505031A5 JP 2007505031 A5 JP2007505031 A5 JP 2007505031A5 JP 2006517916 A JP2006517916 A JP 2006517916A JP 2006517916 A JP2006517916 A JP 2006517916A JP 2007505031 A5 JP2007505031 A5 JP 2007505031A5
- Authority
- JP
- Japan
- Prior art keywords
- cyanomethyl
- cyclohexanecarboxamide
- biphenyl
- alkyl
- thio
- 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
- -1 4 , 4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl Chemical group 0.000 claims 100
- 125000000217 alkyl group Chemical group 0.000 claims 56
- 125000003118 aryl group Chemical group 0.000 claims 25
- 125000005843 halogen group Chemical group 0.000 claims 25
- 125000001072 heteroaryl group Chemical group 0.000 claims 25
- 125000000623 heterocyclic group Chemical group 0.000 claims 20
- 229910052739 hydrogen Inorganic materials 0.000 claims 16
- 239000001257 hydrogen Substances 0.000 claims 16
- 125000001424 substituent group Chemical group 0.000 claims 16
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 13
- 229910052799 carbon Inorganic materials 0.000 claims 11
- 150000001875 compounds Chemical class 0.000 claims 11
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims 10
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims 10
- 125000003545 alkoxy group Chemical group 0.000 claims 9
- 150000002431 hydrogen Chemical class 0.000 claims 9
- PNZXMIKHJXIPEK-UHFFFAOYSA-N cyclohexanecarboxamide Chemical compound NC(=O)C1CCCCC1 PNZXMIKHJXIPEK-UHFFFAOYSA-N 0.000 claims 8
- 150000003839 salts Chemical class 0.000 claims 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 7
- 229930194542 Keto Natural products 0.000 claims 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 7
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 7
- 125000000468 ketone group Chemical group 0.000 claims 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 6
- 125000001188 haloalkyl group Chemical group 0.000 claims 6
- 125000005842 heteroatom Chemical group 0.000 claims 6
- 239000003112 inhibitor Substances 0.000 claims 6
- 150000001204 N-oxides Chemical class 0.000 claims 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 claims 4
- 125000003342 alkenyl group Chemical group 0.000 claims 4
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 3
- 150000001721 carbon Chemical group 0.000 claims 3
- 125000004122 cyclic group Chemical group 0.000 claims 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 3
- LOGFVTREOLYCPF-KXNHARMFSA-N (2s,3r)-2-[[(2r)-1-[(2s)-2,6-diaminohexanoyl]pyrrolidine-2-carbonyl]amino]-3-hydroxybutanoic acid Chemical compound C[C@@H](O)[C@@H](C(O)=O)NC(=O)[C@H]1CCCN1C(=O)[C@@H](N)CCCCN LOGFVTREOLYCPF-KXNHARMFSA-N 0.000 claims 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims 2
- 108091006112 ATPases Proteins 0.000 claims 2
- 102000057290 Adenosine Triphosphatases Human genes 0.000 claims 2
- 229940122361 Bisphosphonate Drugs 0.000 claims 2
- 208000010392 Bone Fractures Diseases 0.000 claims 2
- 229940124638 COX inhibitor Drugs 0.000 claims 2
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 2
- 206010017076 Fracture Diseases 0.000 claims 2
- 102000004286 Hydroxymethylglutaryl CoA Reductases Human genes 0.000 claims 2
- 108090000895 Hydroxymethylglutaryl CoA Reductases Proteins 0.000 claims 2
- 208000037147 Hypercalcaemia Diseases 0.000 claims 2
- 102000003777 Interleukin-1 beta Human genes 0.000 claims 2
- 108090000193 Interleukin-1 beta Proteins 0.000 claims 2
- 241000124008 Mammalia Species 0.000 claims 2
- 208000037848 Metastatic bone disease Diseases 0.000 claims 2
- 208000034578 Multiple myelomas Diseases 0.000 claims 2
- 208000008589 Obesity Diseases 0.000 claims 2
- 208000010191 Osteitis Deformans Diseases 0.000 claims 2
- 206010031243 Osteogenesis imperfecta Diseases 0.000 claims 2
- 208000001132 Osteoporosis Diseases 0.000 claims 2
- 206010035226 Plasma cell myeloma Diseases 0.000 claims 2
- 208000008312 Tooth Loss Diseases 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- 239000003263 anabolic agent Substances 0.000 claims 2
- 229940124325 anabolic agent Drugs 0.000 claims 2
- 150000004663 bisphosphonates Chemical class 0.000 claims 2
- 230000008416 bone turnover Effects 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 239000003255 cyclooxygenase 2 inhibitor Substances 0.000 claims 2
- 239000002834 estrogen receptor modulator Substances 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 201000003617 glucocorticoid-induced osteoporosis Diseases 0.000 claims 2
- 230000000148 hypercalcaemia Effects 0.000 claims 2
- 208000030915 hypercalcemia disease Diseases 0.000 claims 2
- 102000006495 integrins Human genes 0.000 claims 2
- 108010044426 integrins Proteins 0.000 claims 2
- 230000003211 malignant effect Effects 0.000 claims 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 125000002950 monocyclic group Chemical group 0.000 claims 2
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 claims 2
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 claims 2
- 235000020824 obesity Nutrition 0.000 claims 2
- 201000008482 osteoarthritis Diseases 0.000 claims 2
- 208000028169 periodontal disease Diseases 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 229940044551 receptor antagonist Drugs 0.000 claims 2
- 239000002464 receptor antagonist Substances 0.000 claims 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 2
- 239000000849 selective androgen receptor modulator Substances 0.000 claims 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims 1
- GZHDRCGNSZMVBH-UHFFFAOYSA-N 2-(2-bromophenyl)-n-(cyanomethyl)-5,5-difluorocyclohexane-1-carboxamide Chemical compound N#CCNC(=O)C1CC(F)(F)CCC1C1=CC=CC=C1Br GZHDRCGNSZMVBH-UHFFFAOYSA-N 0.000 claims 1
- LXRMOIYSBHNQCC-UHFFFAOYSA-N 2-(3-bromo-1-methylpyrazol-4-yl)-n-(cyanomethyl)-5,5-difluorocyclohexane-1-carboxamide Chemical compound BrC1=NN(C)C=C1C1C(C(=O)NCC#N)CC(F)(F)CC1 LXRMOIYSBHNQCC-UHFFFAOYSA-N 0.000 claims 1
- NRXXMNTVIDJJQS-UHFFFAOYSA-N 2-(3-bromophenyl)-n-(cyanomethyl)-4-methylcyclopentane-1-carboxamide Chemical compound C1C(C)CC(C(=O)NCC#N)C1C1=CC=CC(Br)=C1 NRXXMNTVIDJJQS-UHFFFAOYSA-N 0.000 claims 1
- WKUBQVWCUYLDSA-UHFFFAOYSA-N 2-[2-[4-(1-cyanocyclopropyl)sulfanylphenyl]phenyl]-n-(cyanomethyl)-5,5-difluorocyclohexane-1-carboxamide Chemical compound N#CCNC(=O)C1CC(F)(F)CCC1C1=CC=CC=C1C(C=C1)=CC=C1SC1(C#N)CC1 WKUBQVWCUYLDSA-UHFFFAOYSA-N 0.000 claims 1
- WHLMMOBCVSADIZ-UHFFFAOYSA-N 2-[2-[4-(1h-benzimidazol-2-ylmethylsulfanyl)phenyl]phenyl]-n-(cyanomethyl)-5,5-difluorocyclohexane-1-carboxamide Chemical compound N#CCNC(=O)C1CC(F)(F)CCC1C1=CC=CC=C1C(C=C1)=CC=C1SCC1=NC2=CC=CC=C2N1 WHLMMOBCVSADIZ-UHFFFAOYSA-N 0.000 claims 1
- OOHVZRLNAMHRTG-UHFFFAOYSA-N 2-[2-[4-(1h-benzimidazol-4-ylmethylsulfanyl)phenyl]phenyl]-n-(cyanomethyl)-5,5-difluorocyclohexane-1-carboxamide Chemical compound N#CCNC(=O)C1CC(F)(F)CCC1C1=CC=CC=C1C(C=C1)=CC=C1SCC1=CC=CC2=C1NC=N2 OOHVZRLNAMHRTG-UHFFFAOYSA-N 0.000 claims 1
- HDPGLQRQSCFLMJ-UHFFFAOYSA-N 2-[2-[4-(2-amino-2-oxoethyl)sulfanylphenyl]phenyl]-n-(cyanomethyl)-5,5-difluorocyclohexane-1-carboxamide Chemical compound C1=CC(SCC(=O)N)=CC=C1C1=CC=CC=C1C1C(C(=O)NCC#N)CC(F)(F)CC1 HDPGLQRQSCFLMJ-UHFFFAOYSA-N 0.000 claims 1
- DLGZOUCAOWWJBB-UHFFFAOYSA-N 2-[2-[4-(3h-benzimidazol-5-ylmethylsulfanyl)phenyl]phenyl]-n-(cyanomethyl)-5,5-difluorocyclohexane-1-carboxamide Chemical compound N#CCNC(=O)C1CC(F)(F)CCC1C1=CC=CC=C1C(C=C1)=CC=C1SCC1=CC=C(N=CN2)C2=C1 DLGZOUCAOWWJBB-UHFFFAOYSA-N 0.000 claims 1
- RJWBYOKUGQXZPN-UHFFFAOYSA-N 2-[2-[4-[2-(1h-benzimidazol-2-yl)ethylsulfanyl]phenyl]phenyl]-n-(cyanomethyl)-5,5-difluorocyclohexane-1-carboxamide Chemical compound N#CCNC(=O)C1CC(F)(F)CCC1C1=CC=CC=C1C(C=C1)=CC=C1SCCC1=NC2=CC=CC=C2N1 RJWBYOKUGQXZPN-UHFFFAOYSA-N 0.000 claims 1
- SCVJRXQHFJXZFZ-KVQBGUIXSA-N 2-amino-9-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3h-purine-6-thione Chemical compound C1=2NC(N)=NC(=S)C=2N=CN1[C@H]1C[C@H](O)[C@@H](CO)O1 SCVJRXQHFJXZFZ-KVQBGUIXSA-N 0.000 claims 1
- UUCKWTZQNZNNQT-UHFFFAOYSA-N 3-[2-[2-(cyanomethylcarbamoyl)cyclohexyl]phenyl]benzoic acid Chemical compound OC(=O)C1=CC=CC(C=2C(=CC=CC=2)C2C(CCCC2)C(=O)NCC#N)=C1 UUCKWTZQNZNNQT-UHFFFAOYSA-N 0.000 claims 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- BTGMNPXFKHTLSP-UHFFFAOYSA-N 4-[2-[2-(cyanomethylcarbamoyl)cyclohexyl]phenyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=CC=C1C1C(C(=O)NCC#N)CCCC1 BTGMNPXFKHTLSP-UHFFFAOYSA-N 0.000 claims 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims 1
- PETFKSHTCLWIPJ-UHFFFAOYSA-N 6-(3-bromophenyl)-n-(cyanomethyl)cyclohex-3-ene-1-carboxamide Chemical compound BrC1=CC=CC(C2C(CC=CC2)C(=O)NCC#N)=C1 PETFKSHTCLWIPJ-UHFFFAOYSA-N 0.000 claims 1
- 206010003210 Arteriosclerosis Diseases 0.000 claims 1
- 201000001320 Atherosclerosis Diseases 0.000 claims 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
- 229940093444 Cyclooxygenase 2 inhibitor Drugs 0.000 claims 1
- 108010041356 Estrogen Receptor beta Proteins 0.000 claims 1
- 102100029951 Estrogen receptor beta Human genes 0.000 claims 1
- 208000003076 Osteolysis Diseases 0.000 claims 1
- 208000027868 Paget disease Diseases 0.000 claims 1
- 208000027067 Paget disease of bone Diseases 0.000 claims 1
- 208000011775 arteriosclerosis disease Diseases 0.000 claims 1
- 125000002619 bicyclic group Chemical group 0.000 claims 1
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- 210000003969 blast cell Anatomy 0.000 claims 1
- 208000016738 bone Paget disease Diseases 0.000 claims 1
- 210000000988 bone and bone Anatomy 0.000 claims 1
- 210000002449 bone cell Anatomy 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 230000009089 cytolysis Effects 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims 1
- 208000029791 lytic metastatic bone lesion Diseases 0.000 claims 1
- 208000027202 mammary Paget disease Diseases 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- HPMHPWMBCGNQEX-UHFFFAOYSA-N n-(cyanomethyl)-2-[2-[4-(cyanomethylsulfanyl)phenyl]phenyl]-5,5-difluorocyclohexane-1-carboxamide Chemical compound N#CCNC(=O)C1CC(F)(F)CCC1C1=CC=CC=C1C1=CC=C(SCC#N)C=C1 HPMHPWMBCGNQEX-UHFFFAOYSA-N 0.000 claims 1
- LICNCSINLCCHBN-UHFFFAOYSA-N n-(cyanomethyl)-2-[2-[4-[2-(cyanomethylamino)-2-oxoethyl]sulfanylphenyl]phenyl]-5,5-difluorocyclohexane-1-carboxamide Chemical compound N#CCNC(=O)C1CC(F)(F)CCC1C1=CC=CC=C1C1=CC=C(SCC(=O)NCC#N)C=C1 LICNCSINLCCHBN-UHFFFAOYSA-N 0.000 claims 1
- QIWMDLKBVSBQEY-UHFFFAOYSA-N n-(cyanomethyl)-2-ethynylcyclohexane-1-carboxamide Chemical compound N#CCNC(=O)C1CCCCC1C#C QIWMDLKBVSBQEY-UHFFFAOYSA-N 0.000 claims 1
- FCEQQFKEGCCEFS-UHFFFAOYSA-N n-(cyanomethyl)-2-phenylcyclohexane-1-carboxamide Chemical compound N#CCNC(=O)C1CCCCC1C1=CC=CC=C1 FCEQQFKEGCCEFS-UHFFFAOYSA-N 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 210000000963 osteoblast Anatomy 0.000 claims 1
- 210000002997 osteoclast Anatomy 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 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
- 229940124597 therapeutic agent Drugs 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US48367803P | 2003-06-30 | 2003-06-30 | |
| US60/483,678 | 2003-06-30 | ||
| PCT/CA2004/000948 WO2005000800A1 (en) | 2003-06-30 | 2004-06-28 | Cathepsin cysteine protease inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2007505031A JP2007505031A (ja) | 2007-03-08 |
| JP2007505031A5 true JP2007505031A5 (enExample) | 2007-08-02 |
| JP4690319B2 JP4690319B2 (ja) | 2011-06-01 |
Family
ID=33552066
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006517916A Expired - Fee Related JP4690319B2 (ja) | 2003-06-30 | 2004-06-28 | カテプシンシステインプロテアーゼ阻害剤 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US7405229B2 (enExample) |
| EP (1) | EP1644326B1 (enExample) |
| JP (1) | JP4690319B2 (enExample) |
| CN (1) | CN100393700C (enExample) |
| AU (1) | AU2004251794B2 (enExample) |
| CA (1) | CA2530068A1 (enExample) |
| WO (1) | WO2005000800A1 (enExample) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1841419A4 (en) * | 2005-01-19 | 2009-02-25 | Merck Frosst Canada Ltd | CATHEPSIN K AND ADIPOSITAS INHIBITORS |
| PT1855674E (pt) | 2005-03-02 | 2014-10-08 | Merck Canada Inc | Composição para a inibição de catepsina k |
| WO2006094003A1 (en) * | 2005-03-02 | 2006-09-08 | Glaxo Group Limited | Novel cathepsin c inhibitors and their use |
| EP1902031B1 (en) * | 2005-07-06 | 2012-04-11 | Merck Canada Inc. | Cathepsin cysteine protease inhibitors |
| EP1921080B1 (en) * | 2006-11-07 | 2009-08-05 | Sanofi-Aventis | Subsitituted 8-piperidinyl-2-pyridinyl-pyrimido(1,2-a)pyrimidin-6-one and 8-piperidinyl-2-pyrimidinyl-pyrimido(1,2-a)pyrimidin-6-one derivatives |
| EP2168600A1 (en) | 2007-06-08 | 2010-03-31 | Nippon Chemiphar Co., Ltd. | Therapeutic or prophylactic agent for cerebral aneurysm |
| EP2216047A4 (en) | 2007-10-24 | 2011-12-28 | Nat Univ Corp Tokyo Med & Dent | Regulator for signaling of toll-like receptor, which comprises cathepsin inhibitor as active ingredient |
| US7893099B2 (en) * | 2009-06-11 | 2011-02-22 | Hoffman-La Roche Inc. | Cyclopentane derivatives |
| GB0913345D0 (en) | 2009-07-31 | 2009-09-16 | Astrazeneca Ab | New combination 802 |
| WO2011061527A1 (en) | 2009-11-17 | 2011-05-26 | Astrazeneca Ab | Combinations comprising a glucocorticoid receptor modulator for the treatment of respiratory diseases |
| GB201021992D0 (en) | 2010-12-23 | 2011-02-02 | Astrazeneca Ab | Compound |
| GB201021979D0 (en) | 2010-12-23 | 2011-02-02 | Astrazeneca Ab | New compound |
| JP6454335B2 (ja) * | 2013-10-08 | 2019-01-16 | メルク・シャープ・アンド・ドーム・コーポレーションＭｅｒｃｋ Ｓｈａｒｐ ＆ Ｄｏｈｍｅ Ｃｏｒｐ． | カテプシンシステインプロテアーゼ阻害剤 |
| WO2015051479A1 (en) * | 2013-10-08 | 2015-04-16 | Merck Sharp & Dohme Corp. | Cathepsin cysteine protease inhibitors |
| WO2015120580A1 (en) * | 2014-02-11 | 2015-08-20 | Merck Sharp & Dohme Corp. | Cathepsin cysteine protease inhibitors |
| CN104098501B (zh) * | 2014-06-23 | 2016-07-27 | 华东师范大学 | 3-二氟烷基取代的全碳季碳氧化吲哚衍生物及其合成方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9903861D0 (en) * | 1999-02-20 | 1999-04-14 | Zeneca Ltd | Chemical compounds |
| CA2379747C (en) * | 1999-07-30 | 2008-09-23 | Boehringer Ingelheim Pharmaceuticals, Inc. | Novel succinate derivative compounds useful as cysteine protease inhibitors |
| JP2001139534A (ja) * | 1999-11-16 | 2001-05-22 | Yoshimitsu Nagao | バリン誘導体およびその用途 |
| GB0003111D0 (en) * | 2000-02-10 | 2000-03-29 | Novartis Ag | Organic compounds |
| US6462076B2 (en) * | 2000-06-14 | 2002-10-08 | Hoffmann-La Roche Inc. | Beta-amino acid nitrile derivatives as cathepsin K inhibitors |
| US7012075B2 (en) * | 2001-03-02 | 2006-03-14 | Merck & Co., Inc. | Cathepsin cysteine protease inhibitors |
| AU2002352663B2 (en) * | 2001-11-13 | 2007-06-21 | Axys Pharmaceuticals, Inc. | Cyanoalkylamino derivatives as protease inhibitors |
| SE0201977D0 (sv) * | 2002-06-24 | 2002-06-24 | Astrazeneca Ab | Novel compounds |
-
2004
- 2004-06-28 JP JP2006517916A patent/JP4690319B2/ja not_active Expired - Fee Related
- 2004-06-28 AU AU2004251794A patent/AU2004251794B2/en not_active Ceased
- 2004-06-28 WO PCT/CA2004/000948 patent/WO2005000800A1/en not_active Ceased
- 2004-06-28 CA CA002530068A patent/CA2530068A1/en not_active Abandoned
- 2004-06-28 US US10/560,672 patent/US7405229B2/en not_active Expired - Lifetime
- 2004-06-28 CN CNB2004800184315A patent/CN100393700C/zh not_active Expired - Fee Related
- 2004-06-28 EP EP04737887.2A patent/EP1644326B1/en not_active Expired - Lifetime
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