AU2007246779B2 - Compounds for the treatment of cell proliferative disorders - Google Patents
Compounds for the treatment of cell proliferative disorders Download PDFInfo
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- AU2007246779B2 AU2007246779B2 AU2007246779A AU2007246779A AU2007246779B2 AU 2007246779 B2 AU2007246779 B2 AU 2007246779B2 AU 2007246779 A AU2007246779 A AU 2007246779A AU 2007246779 A AU2007246779 A AU 2007246779A AU 2007246779 B2 AU2007246779 B2 AU 2007246779B2
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- C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
- C07C233/17—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/22—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to an acyclic carbon atom of a carbon skeleton containing six-membered aromatic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/32—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
- C07C235/34—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
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- Enzymes And Modification Thereof (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
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| PCT/IB2007/002471 WO2007129226A2 (en) | 2006-05-09 | 2007-05-09 | Use of syk tyrosine kinase inhibitors for the treatment of cell proliferative disorders |
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| US7674829B2 (en) * | 2004-03-26 | 2010-03-09 | Novaremed Limited | Compounds for the treatment of AIDS and other viral diseases |
| GB0804213D0 (en) | 2008-03-06 | 2008-04-16 | New Era Biotech Ltd | A method of printing or preventing pain |
| ES2770362T3 (es) * | 2009-09-09 | 2020-07-01 | Novaremed Ltd | Bencenopropanamida N-sustituida para su uso en el tratamiento del dolor y la inflamación |
| US8802734B2 (en) * | 2009-09-09 | 2014-08-12 | Novaremed Limited | Method of treating or preventing pain |
| CA2890105C (en) | 2012-11-01 | 2023-03-21 | Infinity Pharmaceuticals, Inc. | Treatment of cancers using pi3 kinase isoform modulators |
| WO2014151386A1 (en) | 2013-03-15 | 2014-09-25 | Infinity Pharmaceuticals, Inc. | Salts and solid forms of isoquinolinones and composition comprising and methods of using the same |
| BR112015029969A2 (pt) | 2013-05-30 | 2017-07-25 | Infinity Pharmaceuticals Inc | tratamento de câncer usando moduladores de isoformas quinase pi3 |
| SG10201902074UA (en) | 2013-10-04 | 2019-04-29 | Infinity Pharmaceuticals Inc | Heterocyclic compounds and uses thereof |
| WO2015051241A1 (en) | 2013-10-04 | 2015-04-09 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
| WO2015061204A1 (en) | 2013-10-21 | 2015-04-30 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
| CN113616656B (zh) | 2014-03-19 | 2023-02-17 | 无限药品股份有限公司 | 用于治疗PI3K-γ介导的障碍的杂环化合物 |
| WO2015160986A2 (en) | 2014-04-16 | 2015-10-22 | Infinity Pharmaceuticals, Inc. | Combination therapies |
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| WO2017214269A1 (en) | 2016-06-08 | 2017-12-14 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
| WO2017223422A1 (en) | 2016-06-24 | 2017-12-28 | Infinity Pharmaceuticals, Inc. | Combination therapies |
| KR20210142154A (ko) | 2019-03-21 | 2021-11-24 | 옹쎄오 | 암 치료를 위한 키나제 억제제와 조합된 dbait 분자 |
| JP2023500906A (ja) | 2019-11-08 | 2023-01-11 | インサーム（インスティテュ ナシオナル ドゥ ラ サンテ エ ドゥ ラ ルシェルシェ メディカル） | キナーゼ阻害剤に対する獲得抵抗性を有するがんの処置方法 |
| WO2021148581A1 (en) | 2020-01-22 | 2021-07-29 | Onxeo | Novel dbait molecule and its use |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004031129A2 (en) * | 2002-10-03 | 2004-04-15 | New Era Biotech, Ltd. | Compounds for use in the treatment of autoimmune diseases, immuno-allergical diseases and organ or tissue transplantation rejection |
| WO2005092305A2 (en) * | 2004-03-26 | 2005-10-06 | New Era Biotech Ltd | Compounds for treating aids and other diseases |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1908322A (en) * | 1932-04-07 | 1933-05-09 | Claude R Cook | Weed puller |
| US2908691A (en) * | 1958-07-14 | 1959-10-13 | Searle & Co | Hydroxyphenalkylaminoalkylindoles and ethers corresponding thereto |
| US4766106A (en) * | 1985-06-26 | 1988-08-23 | Cetus Corporation | Solubilization of proteins for pharmaceutical compositions using polymer conjugation |
| US5539122A (en) * | 1989-05-23 | 1996-07-23 | Abbott Laboratories | Retroviral protease inhibiting compounds |
| IS2334B (is) * | 1992-09-08 | 2008-02-15 | Vertex Pharmaceuticals Inc., (A Massachusetts Corporation) | Aspartyl próteasi hemjari af nýjum flokki súlfonamíða |
| GB0115109D0 (en) * | 2001-06-21 | 2001-08-15 | Aventis Pharma Ltd | Chemical compounds |
-
2007
- 2007-05-09 JP JP2009508544A patent/JP5225264B2/ja not_active Expired - Fee Related
- 2007-05-09 US US12/227,104 patent/US20090306214A1/en not_active Abandoned
- 2007-05-09 PL PL07804842T patent/PL2026775T3/pl unknown
- 2007-05-09 EP EP07804842.8A patent/EP2026775B1/en not_active Not-in-force
- 2007-05-09 ES ES07804842.8T patent/ES2542344T3/es active Active
- 2007-05-09 DK DK07804842.8T patent/DK2026775T3/en active
- 2007-05-09 WO PCT/IB2007/002471 patent/WO2007129226A2/en not_active Ceased
- 2007-05-09 PT PT78048428T patent/PT2026775E/pt unknown
- 2007-05-09 HU HUE07804842A patent/HUE026820T2/en unknown
- 2007-05-09 CA CA2651375A patent/CA2651375C/en not_active Expired - Fee Related
- 2007-05-09 AU AU2007246779A patent/AU2007246779B2/en not_active Ceased
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2008
- 2008-11-06 IL IL195152A patent/IL195152A/en active IP Right Grant
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2012
- 2012-01-06 US US13/344,976 patent/US20120108666A1/en not_active Abandoned
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2013
- 2013-10-09 US US14/049,454 patent/US20140039060A1/en not_active Abandoned
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004031129A2 (en) * | 2002-10-03 | 2004-04-15 | New Era Biotech, Ltd. | Compounds for use in the treatment of autoimmune diseases, immuno-allergical diseases and organ or tissue transplantation rejection |
| WO2005092305A2 (en) * | 2004-03-26 | 2005-10-06 | New Era Biotech Ltd | Compounds for treating aids and other diseases |
Non-Patent Citations (3)
| Title |
|---|
| LIN L. et al.: Journal of Natural Products, 3 May 2006, vol. 69, no. 5, pp. 842-844 * |
| NESTERENKO V. et al.: Journal of the American Chemical Society, 2003, vol. 125, no. 48, pp. 14672-14673 * |
| PARK J.B. & SCHOENE N: Cancer Letters, 2003, vol. 202, no. 2, pp. 161-171 * |
Also Published As
| Publication number | Publication date |
|---|---|
| JP5225264B2 (ja) | 2013-07-03 |
| EP2026775A2 (en) | 2009-02-25 |
| CA2651375C (en) | 2015-12-22 |
| PL2026775T3 (pl) | 2015-12-31 |
| WO2007129226A3 (en) | 2008-05-08 |
| AU2007246779A1 (en) | 2007-11-15 |
| ES2542344T3 (es) | 2015-08-04 |
| HUE026820T2 (en) | 2016-07-28 |
| IL195152A0 (en) | 2009-09-22 |
| CA2651375A1 (en) | 2007-11-15 |
| EP2026775B1 (en) | 2015-04-29 |
| IL195152A (en) | 2015-10-29 |
| DK2026775T3 (en) | 2015-06-29 |
| JP2009536191A (ja) | 2009-10-08 |
| PT2026775E (pt) | 2015-08-05 |
| US20090306214A1 (en) | 2009-12-10 |
| US20140039060A1 (en) | 2014-02-06 |
| US20120108666A1 (en) | 2012-05-03 |
| WO2007129226A2 (en) | 2007-11-15 |
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Owner name: NOVAREMED LTD Free format text: FORMER APPLICANT(S): NEW ERA BIOTECH LTD |
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| FGA | Letters patent sealed or granted (standard patent) | ||
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |