JP2011509282A5 - - Google Patents
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- Publication number
- JP2011509282A5 JP2011509282A5 JP2010541840A JP2010541840A JP2011509282A5 JP 2011509282 A5 JP2011509282 A5 JP 2011509282A5 JP 2010541840 A JP2010541840 A JP 2010541840A JP 2010541840 A JP2010541840 A JP 2010541840A JP 2011509282 A5 JP2011509282 A5 JP 2011509282A5
- Authority
- JP
- Japan
- Prior art keywords
- furo
- benzamide
- pyrrole
- oxodihydro
- oxopentan
- 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
- 150000001875 compounds Chemical class 0.000 claims 56
- -1 tert-butylmethyl Chemical group 0.000 claims 35
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 32
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 18
- 238000000034 method Methods 0.000 claims 14
- 102000005927 Cysteine Proteases Human genes 0.000 claims 6
- 108010005843 Cysteine Proteases Proteins 0.000 claims 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 5
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 claims 4
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
- 102000035195 Peptidases Human genes 0.000 claims 3
- 108091005804 Peptidases Proteins 0.000 claims 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 239000007800 oxidant agent Substances 0.000 claims 3
- 235000019833 protease Nutrition 0.000 claims 3
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 2
- 208000001132 Osteoporosis Diseases 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims 2
- 230000027455 binding Effects 0.000 claims 2
- 230000008355 cartilage degradation Effects 0.000 claims 2
- 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 2
- 239000003085 diluting agent Substances 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 239000003550 marker Substances 0.000 claims 2
- 239000011159 matrix material Substances 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 238000012544 monitoring process Methods 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims 2
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims 2
- 239000000651 prodrug Substances 0.000 claims 2
- 229940002612 prodrug Drugs 0.000 claims 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 125000006239 protecting group Chemical group 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
- 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 claims 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 206010001935 American trypanosomiasis Diseases 0.000 claims 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims 1
- 206010005949 Bone cancer Diseases 0.000 claims 1
- 208000018084 Bone neoplasm Diseases 0.000 claims 1
- 208000024699 Chagas disease Diseases 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 208000037147 Hypercalcaemia Diseases 0.000 claims 1
- 208000030136 Marchiafava-Bignami Disease Diseases 0.000 claims 1
- 208000029725 Metabolic bone disease Diseases 0.000 claims 1
- 206010027476 Metastases Diseases 0.000 claims 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 1
- VNBIOZZRLZAUGX-UHFFFAOYSA-N N-(4-propylpiperazin-1-yl)benzamide Chemical compound C(C1=CC=CC=C1)(=O)NN1CCN(CC1)CCC VNBIOZZRLZAUGX-UHFFFAOYSA-N 0.000 claims 1
- 150000001204 N-oxides Chemical class 0.000 claims 1
- 208000010191 Osteitis Deformans Diseases 0.000 claims 1
- 208000027868 Paget disease Diseases 0.000 claims 1
- 241000223109 Trypanosoma cruzi Species 0.000 claims 1
- 102000004142 Trypsin Human genes 0.000 claims 1
- 108090000631 Trypsin Proteins 0.000 claims 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 1
- 238000010171 animal model Methods 0.000 claims 1
- 210000000988 bone and bone Anatomy 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 238000012875 competitive assay Methods 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 1
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 claims 1
- 235000018417 cysteine Nutrition 0.000 claims 1
- ASQQEOXYFGEFKQ-UHFFFAOYSA-N dioxirane Chemical compound C1OO1 ASQQEOXYFGEFKQ-UHFFFAOYSA-N 0.000 claims 1
- 208000024693 gingival disease Diseases 0.000 claims 1
- 150000004677 hydrates Chemical class 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 230000000148 hypercalcaemia Effects 0.000 claims 1
- 208000030915 hypercalcemia disease Diseases 0.000 claims 1
- 238000000338 in vitro Methods 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 230000003993 interaction Effects 0.000 claims 1
- 201000004792 malaria Diseases 0.000 claims 1
- 208000027202 mammary Paget disease Diseases 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 230000009401 metastasis Effects 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 claims 1
- 125000001064 morpholinomethyl group Chemical group [H]C([H])(*)N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 claims 1
- BLMYFOVRPAQMPC-UHFFFAOYSA-N n-(4-methylpiperazin-1-yl)benzamide Chemical compound C1CN(C)CCN1NC(=O)C1=CC=CC=C1 BLMYFOVRPAQMPC-UHFFFAOYSA-N 0.000 claims 1
- BOPPLEMOWZYQJH-UHFFFAOYSA-N n-[2-(4-methylpiperazin-1-yl)-1,3-thiazol-4-yl]benzamide Chemical compound C1CN(C)CCN1C1=NC(NC(=O)C=2C=CC=CC=2)=CS1 BOPPLEMOWZYQJH-UHFFFAOYSA-N 0.000 claims 1
- 230000001613 neoplastic effect Effects 0.000 claims 1
- 201000008482 osteoarthritis Diseases 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 238000000159 protein binding assay Methods 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 1
- 239000012588 trypsin Substances 0.000 claims 1
- 0 Cc(cc1)ccc1N1CCN(*)CC1 Chemical compound Cc(cc1)ccc1N1CCN(*)CC1 0.000 description 4
- UPATXVAGIAHYGQ-CFCGPWAMSA-N C=C=CC1[C@H]2OCC[C@H]2OC1 Chemical compound C=C=CC1[C@H]2OCC[C@H]2OC1 UPATXVAGIAHYGQ-CFCGPWAMSA-N 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0800338.6 | 2008-01-08 | ||
| GB0800338A GB0800338D0 (en) | 2008-01-09 | 2008-01-09 | Compounds |
| GB0808669A GB0808669D0 (en) | 2008-05-13 | 2008-05-13 | Compounds |
| GB0808669.6 | 2008-05-13 | ||
| PCT/GB2009/000039 WO2009087379A2 (en) | 2008-01-09 | 2009-01-07 | Tetrahydrofuro (3, 2 -b) pyrrol- 3 -one derivatives as inhibitors of cysteine proteinases |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2011509282A JP2011509282A (ja) | 2011-03-24 |
| JP2011509282A5 true JP2011509282A5 (enExample) | 2012-02-23 |
| JP5587790B2 JP5587790B2 (ja) | 2014-09-10 |
Family
ID=40791443
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010541840A Expired - Fee Related JP5587790B2 (ja) | 2008-01-09 | 2009-01-07 | 化合物 |
Country Status (4)
| Country | Link |
|---|---|
| US (3) | US8501744B2 (enExample) |
| EP (2) | EP2240491B1 (enExample) |
| JP (1) | JP5587790B2 (enExample) |
| WO (1) | WO2009087379A2 (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU581929B2 (en) * | 1985-09-16 | 1989-03-09 | Schering Corporation | Antihypertensive agents, pharmaceutical compositions containing them and processes for the preparation of the agents and compositions |
| GB0817424D0 (en) | 2008-09-24 | 2008-10-29 | Medivir Ab | Protease inhibitors |
| AU2013305759C1 (en) | 2012-08-23 | 2018-01-18 | Janssen Biopharma, Inc. | Compounds for the treatment of paramoxyvirus viral infections |
| US9540391B2 (en) | 2013-01-17 | 2017-01-10 | Sanofi | Isomannide derivatives as inhibitors of soluble epoxide hydrolase |
| SG11201600977XA (en) * | 2013-08-21 | 2016-03-30 | Alios Biopharma Inc | Antiviral compounds |
| MX377396B (es) | 2013-09-12 | 2025-03-10 | Janssen Biopharma Inc | Compuestos de azapiridona y usos de los mismos. |
| MA41614A (fr) | 2015-02-25 | 2018-01-02 | Alios Biopharma Inc | Composés antiviraux |
| GB201506660D0 (en) | 2015-04-20 | 2015-06-03 | Cellcentric Ltd | Pharmaceutical compounds |
| GB201506658D0 (en) | 2015-04-20 | 2015-06-03 | Cellcentric Ltd | Pharmaceutical compounds |
Family Cites Families (61)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3444216A (en) | 1966-11-16 | 1969-05-13 | Upjohn Co | Process for the oxidation of primary and secondary alcohols |
| NZ207394A (en) | 1983-03-08 | 1987-03-06 | Commw Serum Lab Commission | Detecting or determining sequence of amino acids |
| US5128448A (en) | 1990-01-10 | 1992-07-07 | Hoffman-La Roche Inc. | CCK analogs with appetite regulating activity |
| US5374623A (en) | 1992-08-20 | 1994-12-20 | Prototek, Inc. | Cysteine protease inhibitors effective for in vivo use |
| CA2111930A1 (en) | 1992-12-25 | 1994-06-26 | Ryoichi Ando | Aminoketone derivatives |
| DZ2285A1 (fr) | 1996-08-08 | 2002-12-25 | Smithkline Beecham Corp | Inhibiteurs de protéase de la cystéine. |
| US6043218A (en) | 1996-10-22 | 2000-03-28 | Medical University Of South Carolina | Positively charged non-natural amino acids, methods of making thereof, and use thereof in peptides |
| AR013079A1 (es) | 1997-05-06 | 2000-12-13 | Smithkline Beecham Corp | Derivados sustituidos de tetrahidrofurano-3-onas, de tetrahidropirano-3- onas y tetrahidrotiofen-3-onas, un procedimiento para su preparacion unacomposicion farmaceutica de un medicamento util como inhibidores de proteasas e intermediarios |
| CN1273444C (zh) | 1997-11-05 | 2006-09-06 | 诺瓦提斯公司 | 二肽腈 |
| GB9806287D0 (en) | 1998-03-24 | 1998-05-20 | Synphar Lab Inc | Monobactam enzyme inhibitors |
| MA26618A1 (fr) | 1998-04-09 | 2004-12-20 | Smithkline Beecham Corp | Composes et compositions pharmaceutiques pour le traitement du paludisme |
| DZ2815A1 (fr) | 1998-06-12 | 2003-12-01 | Smithkline Beecham Corp | Inhibiteurs de protéase. |
| CA2301201A1 (en) | 1998-08-14 | 2000-02-24 | Smithkline Beecham Corporation | Method of inhibiting cathepsin k |
| ES2142773B1 (es) | 1998-10-07 | 2001-01-01 | Lacer Sa | Derivados de mononitrato de isosorbida y su empleo como agentes vasodilatadores con tolerancia desminuida. |
| CO5150165A1 (es) | 1998-11-13 | 2002-04-29 | Smithkline Beecham Plc | Inhibidores de proteasa: tipo catepsina k |
| WO2000049007A1 (en) | 1999-02-20 | 2000-08-24 | Astrazeneca Ab | Acetamido acetonitrile derivatives as inhibitors of cathepsin l and/or cathepsin s |
| AU2560000A (en) | 1999-02-20 | 2000-09-04 | Astrazeneca Ab | Di- and tripeptide nitrile derivatives as inhibitors of cathepsin l and cathepsin |
| GB9903861D0 (en) | 1999-02-20 | 1999-04-14 | Zeneca Ltd | Chemical compounds |
| WO2000051998A1 (en) | 1999-03-02 | 2000-09-08 | Boehringer Ingelheim Pharmaceuticals, Inc. | Compounds useful as reversible inhibitors of cathepsin s |
| US6506733B1 (en) | 1999-03-15 | 2003-01-14 | Axys Pharmaceuticals, Inc. | Compounds and compositions as protease inhibitors |
| DE60021254T2 (de) | 1999-03-15 | 2006-04-20 | AXYS Pharmaceuticals, Inc., South San Francisco | N-cyanomethylamide als protease inhibitoren |
| TW200404789A (en) | 1999-03-15 | 2004-04-01 | Axys Pharm Inc | Novel compounds and compositions as protease inhibitors |
| GB9907683D0 (en) | 1999-04-06 | 1999-05-26 | Synphar Lab Inc | Substituted azetidin-2-ones as cysteine protease inhibitors |
| GB9911417D0 (en) | 1999-05-18 | 1999-07-14 | Peptide Therapeutics Ltd | Furanone derivatives as inhibitors of cathepsin s |
| GB9917909D0 (en) | 1999-07-31 | 1999-09-29 | Synphar Lab Inc | Cysteine protease inhibitors |
| US6680836B1 (en) | 1999-08-03 | 2004-01-20 | Siemens Aktiengesellschaft | Timed tripping circuit for an electromechanical switching device |
| US6420364B1 (en) | 1999-09-13 | 2002-07-16 | Boehringer Ingelheim Pharmaceuticals, Inc. | Compound useful as reversible inhibitors of cysteine proteases |
| SK286463B6 (sk) | 1999-09-13 | 2008-10-07 | Boehringer Ingelheim Pharmaceuticals, Inc. | Spiroheterocyklické zlúčeniny, spôsob ich výroby,farmaceutický prostriedok s ich obsahom a ich použitie |
| AU7490900A (en) | 1999-09-16 | 2001-04-17 | Axys Pharmaceuticals, Inc. | Chemical compounds and compositions and their use as cathepsin s inhibitors |
| GB9925264D0 (en) | 1999-10-26 | 1999-12-29 | Zeneca Ltd | Chemical compounds |
| EP1229915A4 (en) | 1999-11-10 | 2003-05-14 | Smithkline Beecham Corp | PROTEASE INHIBITORS |
| WO2001034153A1 (en) | 1999-11-10 | 2001-05-17 | Smithkline Beecham Corporation | Protease inhibitors |
| DE60030768T2 (de) | 1999-12-24 | 2007-11-08 | F. Hoffmann-La Roche Ag | Nitrilderivate als cathepsin k hemmer |
| US6525036B2 (en) | 2000-01-06 | 2003-02-25 | Merck & Co., Inc. | Compounds and compositions as protease inhibitors |
| GB0003111D0 (en) | 2000-02-10 | 2000-03-29 | Novartis Ag | Organic compounds |
| WO2001068645A2 (en) | 2000-03-15 | 2001-09-20 | Axys Pharmaceuticals, Inc. | N-cyanomethylcarboxamides and their use as protease inhibitors |
| US7071184B2 (en) | 2000-03-21 | 2006-07-04 | Smithkline Beecham Corporation | Protease inhibitors |
| AU2001256981A1 (en) | 2000-04-06 | 2001-10-23 | Axys Pharmaceuticals, Inc. | Cathepsin cysteine protease inhibitors |
| CO5280093A1 (es) | 2000-04-18 | 2003-05-30 | Smithkline Beecham Corp | Metodos de tratamiento |
| US6462076B2 (en) | 2000-06-14 | 2002-10-08 | Hoffmann-La Roche Inc. | Beta-amino acid nitrile derivatives as cathepsin K inhibitors |
| AU2001268407A1 (en) | 2000-06-14 | 2001-12-24 | Smithkline Beecham Corporation | Protease inhibitors |
| WO2002017924A1 (en) | 2000-09-01 | 2002-03-07 | Smithkline Beecham Corporation | Method of treatment |
| CA2426271A1 (en) | 2000-10-19 | 2002-04-25 | Naeja Pharmaceutical Inc. | Dihydropyrimidine derivatives as cysteine protease inhibitors |
| MXPA03005601A (es) | 2000-12-22 | 2004-12-02 | Axys Pharm Inc | Nuevos compuestos y composiciones como inhibidores de catepsina. |
| EP1362052B1 (en) * | 2001-01-17 | 2007-03-07 | Amura Therapeutics Limited | Inhibitors of cruzipain and other cysteine proteases |
| JP2004520365A (ja) | 2001-01-17 | 2004-07-08 | アミュラ テラピューティクス リミテッド | クルジパインおよび他のシステインプロテアーゼの阻害剤 |
| WO2002080920A1 (en) | 2001-04-06 | 2002-10-17 | Axys Pharmaceuticals, Inc. | Arylacetamido-ketobenzoxazole as cysteine protease inhibitors |
| AU2002342682A1 (en) | 2001-05-17 | 2002-11-25 | Smithkline Beecham Corporation | Protease inhibitors |
| FR2826572B1 (fr) | 2001-06-29 | 2005-10-07 | Oreal | Compositions contenant un derive d'hydroxydiphenyl ether inhibant le developpement des odeurs corporelles |
| WO2003013518A1 (en) | 2001-08-03 | 2003-02-20 | Smithkline Beecham Corporation | Alpha-ketoamide derivatives as cathepsin k inhibitors |
| AR036375A1 (es) | 2001-08-30 | 2004-09-01 | Novartis Ag | Compuestos pirrolo [2,3-d] pirimidina -2- carbonitrilo, un proceso para su preparacion, una composicion farmaceutica y el uso de dichos compuestos para la preparacion de medicamentos |
| BR0212535A (pt) | 2001-09-14 | 2004-10-19 | Aventis Pharma Inc | Compostos e composições como inibidores de catepsina |
| CA2459825A1 (en) | 2001-10-02 | 2003-04-10 | Boehringer Ingelheim Pharmaceuticals, Inc. | Compounds useful as reversible inhibitors of cysteine proteases |
| CA2463770A1 (en) | 2001-10-29 | 2003-05-08 | Boehringer Ingelheim Pharmaceuticals, Inc. | Compounds useful as reversible inhibitors of cysteine proteases |
| US7371747B2 (en) | 2001-11-13 | 2008-05-13 | Merck Frosst Canada & Co. | Cyanoalkylamino derivatives as protease inhibitors |
| HRP20040426A2 (en) | 2001-11-14 | 2004-10-31 | Aventis Pharma Inc | Oligopeptides and compositions containing them as cathepsin s inhibitors |
| WO2004007501A1 (en) | 2002-07-16 | 2004-01-22 | Amura Therapeutics Limited | Biologically active compounds |
| WO2005066180A1 (en) * | 2004-01-08 | 2005-07-21 | Medivir Ab | Cysteine protease inhibitors |
| WO2006064286A1 (en) | 2004-12-13 | 2006-06-22 | Medivir Uk Ltd | Cathepsin s inhibitors |
| GB0614044D0 (en) * | 2006-07-14 | 2006-08-23 | Amura Therapeutics Ltd | Compounds |
| GB0614042D0 (en) * | 2006-07-14 | 2006-08-23 | Amura Therapeutics Ltd | Compounds |
-
2009
- 2009-01-07 WO PCT/GB2009/000039 patent/WO2009087379A2/en not_active Ceased
- 2009-01-07 JP JP2010541840A patent/JP5587790B2/ja not_active Expired - Fee Related
- 2009-01-07 EP EP09700614.2A patent/EP2240491B1/en not_active Not-in-force
- 2009-01-07 EP EP20130189094 patent/EP2719700A1/en not_active Withdrawn
-
2010
- 2010-06-25 US US12/823,558 patent/US8501744B2/en not_active Expired - Fee Related
-
2013
- 2013-05-23 US US13/901,479 patent/US9045492B2/en not_active Expired - Fee Related
-
2015
- 2015-04-10 US US14/683,913 patent/US20150209349A1/en not_active Abandoned
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