JP2007502844A5 - - Google Patents
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- Publication number
- JP2007502844A5 JP2007502844A5 JP2006524107A JP2006524107A JP2007502844A5 JP 2007502844 A5 JP2007502844 A5 JP 2007502844A5 JP 2006524107 A JP2006524107 A JP 2006524107A JP 2006524107 A JP2006524107 A JP 2006524107A JP 2007502844 A5 JP2007502844 A5 JP 2007502844A5
- Authority
- JP
- Japan
- Prior art keywords
- mmol
- reaction
- give
- ethyl acetate
- temperature
- 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
Links
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- OPBFFNZNNJKRCS-YFKPBYRVSA-N (2s)-2-hydroxy-4,4-dimethylpentanoic acid Chemical compound CC(C)(C)C[C@H](O)C(O)=O OPBFFNZNNJKRCS-YFKPBYRVSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000000589 high-performance liquid chromatography-mass spectrometry Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US49685803P | 2003-08-20 | 2003-08-20 | |
| US10/922,362 US7256207B2 (en) | 2003-08-20 | 2004-08-18 | Inhibitors of cathepsin S |
| PCT/US2004/027316 WO2005018568A2 (en) | 2003-08-20 | 2004-08-19 | Inhibitors of cathepsin s |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2007502844A JP2007502844A (ja) | 2007-02-15 |
| JP2007502844A5 true JP2007502844A5 (https=) | 2007-10-04 |
Family
ID=34221426
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006524107A Pending JP2007502844A (ja) | 2003-08-20 | 2004-08-19 | カテプシンｓの阻害剤 |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US7256207B2 (https=) |
| EP (1) | EP1658274A4 (https=) |
| JP (1) | JP2007502844A (https=) |
| AU (1) | AU2004266151B2 (https=) |
| BR (1) | BRPI0413755A (https=) |
| CA (1) | CA2534489A1 (https=) |
| MX (1) | MXPA06001888A (https=) |
| WO (1) | WO2005018568A2 (https=) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7256207B2 (en) * | 2003-08-20 | 2007-08-14 | Irm Llc | Inhibitors of cathepsin S |
| TWI389897B (zh) | 2005-02-22 | 2013-03-21 | Chugai Pharmaceutical Co Ltd | 1- (2H) -isoquinolinone derivatives |
| US7751835B2 (en) * | 2005-10-04 | 2010-07-06 | Airvana, Inc. | Non-circular paging areas |
| WO2011069298A1 (en) * | 2009-12-11 | 2011-06-16 | F. Hoffmann-La Roche Ag | Novel cyclopropane indolinone derivatives |
| GB2476823B (en) | 2010-01-11 | 2012-05-02 | Subsea 7 Contracting Uk Ltd | Improvements relating to abandonment and recovery of pipelines |
| CN113272286B (zh) * | 2019-01-22 | 2024-04-16 | 阿德弗里奥药品有限责任公司 | 制备4-(2,2,3,3-四氟丙基)吗啉的方法 |
| WO2020201572A1 (en) | 2019-04-05 | 2020-10-08 | Université De Bretagne Occidentale | Protease-activated receptor-2 inhibitors for the treatment of sensory neuropathy induced by a marine neurotoxic poisoning |
Family Cites Families (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4499295A (en) * | 1983-05-09 | 1985-02-12 | G. D. Searle & Co. | Protease inhibitors |
| US5374623A (en) * | 1992-08-20 | 1994-12-20 | Prototek, Inc. | Cysteine protease inhibitors effective for in vivo use |
| EP0648740B1 (en) * | 1993-04-28 | 1997-10-08 | Kumiai Chemical Industry Co., Ltd. | Amino acid amide derivative, agrohorticultural bactericide, and production process |
| US5648514A (en) | 1994-12-29 | 1997-07-15 | Allergan | Substituted acetylenes having retinoid-like biological activity |
| US5691368A (en) * | 1995-01-11 | 1997-11-25 | Hoechst Marion Roussel, Inc. | Substituted oxazolidine calpain and/or cathepsin B inhibitors |
| US5849711A (en) * | 1995-06-06 | 1998-12-15 | Athena Neurosciences, Inc. | Cathepsin and methods and compositions for inhibition thereof |
| TW438591B (en) * | 1995-06-07 | 2001-06-07 | Arris Pharm Corp | Reversible cysteine protease inhibitors |
| SK48198A3 (en) * | 1995-10-30 | 1998-10-07 | Smithkline Beecham Corp | Cathepsin k molecule, a peptid being bonded to the hollow of active positon of cathepsin k, a composition, method for identification of inhibiting compound and inhibitors being competitively bonded to the active position of cathepsin k |
| WO1997016433A1 (en) * | 1995-10-30 | 1997-05-09 | Smithkline Beecham Corporation | Protease inhibitors |
| DE19610784A1 (de) * | 1996-03-19 | 1997-09-25 | Hoechst Ag | Fluoralkyl- und Fluoralkoxysubstituierte heterocyclische Bradykinin-Antagonisten, Verfahren zu ihrer Herstellung und ihre Verwendung |
| US5840733A (en) | 1996-07-01 | 1998-11-24 | Redcell, Canada, Inc. | Methods and compositions for producing novel conjugates of thrombin inhibitors and endogenous carriers resulting in anti-thrombins with extended lifetimes |
| US5916887A (en) * | 1996-09-23 | 1999-06-29 | National Research Council Of Canada | 4-substituted-3-(2-amino-2-cycloalkyl methyl)-acetamido azetidin-2-one derivatives as cysteine proteinase regulators |
| US6004933A (en) * | 1997-04-25 | 1999-12-21 | Cortech Inc. | Cysteine protease inhibitors |
| TR199902752T2 (xx) * | 1997-05-08 | 2000-06-21 | Smithkline Beecham Corporation | Proteaz inhibit�rleri. |
| GB9723407D0 (en) * | 1997-11-05 | 1998-01-07 | Ciba Geigy Ag | Organic compounds |
| GB9903548D0 (en) | 1999-02-16 | 1999-04-07 | Novartis Ag | Organic compounds |
| EP1159273A1 (en) * | 1999-03-02 | 2001-12-05 | Boehringer Ingelheim Pharmaceuticals Inc. | Compounds useful as reversible inhibitors of cathepsin s |
| DE60021254T2 (de) * | 1999-03-15 | 2006-04-20 | AXYS Pharmaceuticals, Inc., South San Francisco | N-cyanomethylamide als protease inhibitoren |
| CA2379747C (en) * | 1999-07-30 | 2008-09-23 | Boehringer Ingelheim Pharmaceuticals, Inc. | Novel succinate derivative compounds useful as cysteine protease inhibitors |
| US6420364B1 (en) * | 1999-09-13 | 2002-07-16 | Boehringer Ingelheim Pharmaceuticals, Inc. | Compound useful as reversible inhibitors of cysteine proteases |
| ES2199856T3 (es) | 1999-09-13 | 2004-03-01 | Boehringer Ingelheim Pharmaceuticals, Inc. | Nuevos compuestos heterociclicos, utiles como inhibidores reversibles de cisteina proteasas. |
| KR100523119B1 (ko) * | 2000-03-16 | 2005-10-20 | 에프. 호프만-라 로슈 아게 | Ｉｐ 길항제로서의 카복실산 유도체 |
| EP1309591B1 (en) | 2000-08-14 | 2007-01-24 | Ortho-McNeil Pharmaceutical, Inc. | Substituted pyrazoles |
| EP1309593B1 (en) | 2000-08-14 | 2006-03-15 | Ortho-McNeil Pharmaceutical, Inc. | Substituted pyrazoles |
| HK1052705B (en) | 2000-08-14 | 2006-09-29 | Ortho-Mcneil Pharmaceutical, Inc. | Substituted pyrazole |
| MXPA03005601A (es) | 2000-12-22 | 2004-12-02 | Axys Pharm Inc | Nuevos compuestos y composiciones como inhibidores de catepsina. |
| AU2002242500A1 (en) | 2001-03-02 | 2002-09-19 | Merck Frosst Canada And Co. | Cathepsin cysteine protease inhibitors |
| CA2439415C (en) | 2001-03-02 | 2011-09-20 | Merck Frosst Canada & Co. | Cathepsin cysteine protease inhibitors |
| WO2002070519A1 (en) | 2001-03-05 | 2002-09-12 | Axys Pharmaceuticals, Inc. | Monobactams as cathepsin k inhibitors |
| EP1411933A1 (en) | 2001-08-03 | 2004-04-28 | SmithKline Beecham Corporation | Alpha-ketoamide derivatives as cathepsin k inhibitors |
| US20030144234A1 (en) | 2001-08-30 | 2003-07-31 | Buxton Francis Paul | Methods for the treatment of chronic pain and compositions therefor |
| EP1448554A1 (en) * | 2001-10-09 | 2004-08-25 | SmithKline Beecham Corporation | Propylcarbamate derivatives as inhibitors of serine and cysteine proteases |
| US7101880B2 (en) * | 2002-06-24 | 2006-09-05 | Schering Aktiengesellschaft | Peptidic compounds as cysteine protease inhibitors |
| US7256207B2 (en) * | 2003-08-20 | 2007-08-14 | Irm Llc | Inhibitors of cathepsin S |
-
2004
- 2004-08-18 US US10/922,362 patent/US7256207B2/en not_active Expired - Fee Related
- 2004-08-19 BR BRPI0413755-8A patent/BRPI0413755A/pt not_active IP Right Cessation
- 2004-08-19 CA CA002534489A patent/CA2534489A1/en not_active Abandoned
- 2004-08-19 JP JP2006524107A patent/JP2007502844A/ja active Pending
- 2004-08-19 EP EP04781915A patent/EP1658274A4/en not_active Withdrawn
- 2004-08-19 MX MXPA06001888A patent/MXPA06001888A/es active IP Right Grant
- 2004-08-19 AU AU2004266151A patent/AU2004266151B2/en not_active Ceased
- 2004-08-19 WO PCT/US2004/027316 patent/WO2005018568A2/en not_active Ceased
-
2007
- 2007-07-13 US US11/777,879 patent/US7507755B2/en not_active Expired - Fee Related
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