UA73572C2 - 1,2-annelated quinoline enantiomer inhibiting farnesyl transferase - Google Patents
1,2-annelated quinoline enantiomer inhibiting farnesyl transferase Download PDFInfo
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- UA73572C2 UA73572C2 UA20021210152A UA20021210152A UA73572C2 UA 73572 C2 UA73572 C2 UA 73572C2 UA 20021210152 A UA20021210152 A UA 20021210152A UA 20021210152 A UA20021210152 A UA 20021210152A UA 73572 C2 UA73572 C2 UA 73572C2
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- compound
- mixture
- chlorophenyl
- cancer
- farnesyl transferase
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Classifications
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- C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
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Landscapes
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| EP00202181 | 2000-06-22 | ||
| PCT/EP2001/006747 WO2001098302A1 (en) | 2000-06-22 | 2001-06-13 | Farnesyl transferase inhibiting 1,2-annelated quinoline enantiomer |
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| UA73572C2 true UA73572C2 (en) | 2005-08-15 |
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| UA20021210152A UA73572C2 (en) | 2000-06-22 | 2001-06-13 | 1,2-annelated quinoline enantiomer inhibiting farnesyl transferase |
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| HR (1) | HRP20020989B1 (es) |
| HU (1) | HU229095B1 (es) |
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| IS (1) | IS2596B (es) |
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| WO2003018135A1 (en) * | 2001-08-24 | 2003-03-06 | Wyeth Holdings Corporation | Method of using 5-(arylsulfonyl)-,5-(arylsulfinyl), and 5-(arylsulfanyl)-thiazolidine-2,4-diones for inhibition of farnesyl-protein transferase |
| JP4384505B2 (ja) | 2002-04-15 | 2009-12-16 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | ファルネシルトランスフェラーゼを阻害する炭素連結イミダゾールもしくはトリアゾール置換三環状キナゾリン誘導体 |
| US20050003422A1 (en) | 2003-07-01 | 2005-01-06 | Mitch Reponi | Methods for assessing and treating cancer |
| US10076512B2 (en) | 2014-05-01 | 2018-09-18 | Eiger Biopharmaceuticals, Inc. | Treatment of hepatitis delta virus infection |
| US11311519B2 (en) | 2014-05-01 | 2022-04-26 | Eiger Biopharmaceuticals, Inc. | Treatment of hepatitis delta virus infection |
| WO2016090107A2 (en) * | 2014-12-04 | 2016-06-09 | Eiger Biopharmaceuticals, Inc. | Treatment of hepatitis delta virus infection |
| WO2016172342A1 (en) | 2015-04-21 | 2016-10-27 | Eiger Biopharmaceuticals, Inc. | Pharmaceutical compositions comprising lonafarnib and ritonavir |
| ES2787073T3 (es) | 2015-08-17 | 2020-10-14 | Kura Oncology Inc | Métodos para tratar pacientes con cáncer con inhibidores de la farnesiltransferasa |
| HUE053927T2 (hu) | 2016-11-03 | 2021-07-28 | Kura Oncology Inc | Farneziltranszferáz inhibitorok rák kezelésében történõ alkalmazásra |
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| GB1519765A (en) * | 1974-09-05 | 1978-08-02 | Ici Ltd | Pesticidal dihydrotetrazolo(1,5a) quinazolines compositions and processes |
| US4141979A (en) * | 1976-12-23 | 1979-02-27 | Pfizer Inc. | Tetrazolo[a]quinazol-5-ones antiallergy and antiulcer agents |
| GB9513577D0 (en) * | 1995-07-04 | 1995-09-06 | Brotherwood Rodney J | Improvements in passenger carrying vehicles |
| TW349948B (en) * | 1995-10-31 | 1999-01-11 | Janssen Pharmaceutica Nv | Farnesyl transferase inhibiting 2-quinolone derivatives |
| CZ293296B6 (cs) * | 1995-12-08 | 2004-03-17 | Janssen Pharmaceutica N.V. | (Imidazol-5-yl)methyl-2-chinolinonové deriváty inhibující farnesyl protein transferázu |
| WO1997036876A1 (en) | 1996-04-03 | 1997-10-09 | Merck & Co., Inc. | Inhibitors of farnesyl-protein transferase |
| TW591030B (en) * | 1997-03-10 | 2004-06-11 | Janssen Pharmaceutica Nv | Farnesyl transferase inhibiting 1,8-annelated quinolinone derivatives substituted with N- or C-linked imidazoles |
| ATE366250T1 (de) * | 1997-04-25 | 2007-07-15 | Janssen Pharmaceutica Nv | Chinazolinone die farnesyltransferase hemmen |
| ES2182327T3 (es) | 1997-06-02 | 2003-03-01 | Janssen Pharmaceutica Nv | Derivados de (imidazol-5-il)metil-2-quinlinona como inhibidores de la proliferacion de celulas de musculos lisos. |
| BR9911869A (pt) | 1998-07-06 | 2001-03-27 | Janssen Pharmaceutica Nv | Inibidores da transferase da proteìna farnesil para o tratamento das artropatias |
| EE04582B1 (et) * | 1998-07-06 | 2006-02-15 | Janssen Pharmaceutica N.V. | Farnesüülproteiintransferaasi inhibiitorite kasutamine radiosensibiliseerimisomadustega farmatseutilise kompositsiooni valmistamiseks, mis on ette nähtud kasutamiseks vähi kiiritusravis |
| BR9913315A (pt) * | 1998-08-27 | 2001-05-22 | Pfizer Prod Inc | Derivados de quinolin-2-ona úteis como agentes anticâncer |
| AU4925499A (en) * | 1998-08-27 | 2000-03-21 | Pfizer Products Inc. | Alkynyl-substituted quinolin-2-one derivatives useful as anticancer agents |
| PL199080B1 (pl) * | 1998-12-23 | 2008-08-29 | Janssen Pharmaceutica Nv | Pochodna chinoliny o pierścieniu 1,2-skondensowanym i sposób jej otrzymywania, kompozycja farmaceutyczna i sposób jej otrzymywania, pochodna chinoliny i sposób jej otrzymywania |
| US6462201B1 (en) * | 1998-12-29 | 2002-10-08 | Isp Investments Inc. | Process for the production of N-vinyl-2-pyrrolidone by vinylation |
| TR200201296T2 (tr) * | 1999-02-11 | 2002-07-22 | Pfizer Products Inc. | Antikanser maddeleri olarak faydalı heteroaril-ikame edilmiş kinolin-2-on türevleri |
| HN2000000266A (es) | 2000-01-21 | 2001-05-21 | Pfizer Prod Inc | Compuesto anticanceroso y metodo de separacion de enantiomeros util para sintetizar dicho compuesto. |
| WO2001062234A2 (en) | 2000-02-24 | 2001-08-30 | Janssen Pharmaceutica N.V. | Dosing regimen |
| US7196094B2 (en) | 2000-09-25 | 2007-03-27 | Janssen Pharmaceutica, N.V. | Farnesyl transferase inhibiting 6-heterocyclylmethyl quinoline and quinazoline derivatives |
| WO2002024687A1 (en) | 2000-09-25 | 2002-03-28 | Janssen Pharmaceutica N.V. | Farnesyl transferase inhibiting 6-heterocyclylmethyl quinolinone derivatives |
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