- Initial Route Scouting and Final Process Development for the Multi-Kg Production of 3-Fluoro-6-methoxyquinoline from p-Anisidine and 2-Fluoromalonic Acid
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A scalable route to 3-fluoro-6-methoxyquinoline needed to be developed as multi-kg amounts of this heterocycle were required. Initial route development focused on the formation of the key C-F bond via a Balz-Schiemann reaction or electrophilic fluorinatio
- Sch?fer, Gabriel,Fleischer, Tony,Blumer, Nicole,Udry, Megan,Reber, Stefan,Stansfield, Ian,Liu, Yuanhua,Li, Yan,Li, Pixu
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p. 347 - 357
(2022/02/01)
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- SULFONAMIDE COMPOUNDS AND USES AS TNAP INHIBITORS
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Described herein are compounds that modulate the activity of TNAP. In some embodiments, the compounds described herein inhibit TNAP. In certain embodiments, the compounds described herein are useful in the treatment of conditions associated with hyper- mineralization.
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Paragraph 00671
(2013/09/12)
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- PYRIMIDINE DERIVATIVES USED AS PI-3 KINASE INHIBITORS
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Phosphatidylinositol (PI) 3-kinase inhibitor compounds (I), their pharmaceutically acceptable salts, and prodrugs thereof ; compositions of the new compounds, either alone or in combination with at least one additional therapeutic agent, with a pharmaceutically acceptable carrier; and uses of the new compounds, either alone or in combination with at least one additional therapeutic agent, in the prophylaxis or treatment of proliferative diseases characterized by the abnormal activity of growth factors, protein serine/threonine kinases, and phospholipid kinases.
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Page/Page column 114-115
(2010/11/28)
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- ACETAMIDE COMPOUNDS AS FUNGICIDES
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Compounds of the general formula (I); wherein the substituents are as defined in claim 1, are useful as fungicides.
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Page/Page column 89
(2010/11/08)
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- Novel process for preparing 3-fluoroquinolines
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The invention relates to a novel preparation of 3-fluoroquinolines of formula (I) in which R1, R2, R3 and R4 represent: a) a fluorine; b) an alkyl optionally substituted with one to three fluorines, with OR
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Page/Page column 4
(2008/06/13)
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- Synthetic and mechanistic studies on the azabicyclo[7.3.1]enediyne core and naphtho[2,3-h]quinoline portions of dynemicin A
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The synthesis of the 13-keto-10-azabicyclo[7.3.1]enediyne core structure of dynemicin A has been achieved by two routes, Schemes 4 and 6. The chemistry of the 13-keto core structure is dominated by the unusually facile bridgehead enolization. Comparison of the rates of cycloaromatization of a variety of enediynes revealed that substantial rate differences occurred even though the distance between the bonding acetylenes was virtually identical. A non-radical cycloaromatization pathway, initiated by thiol addition to the enediyne system, was discovered, and the simple core amine 26 exhibits modest in vitro and in vivo antitumor activity. Finally, two methods for the synthesis of the naphtho[2,3-h]quinoline portion of dynemicin A are described, and both these compounds also exhibit antitumor activity.
- Magnus, Philip,Eisenbeis, Shane A.,Fairhurst, Robin A.,Iliadis, Theodore,Magnus, Nicholas A.,Parry, David
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p. 5591 - 5605
(2007/10/03)
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- Synthesis of tetrahydroquinoline enediyne core analogs of dynemicin
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A process is described for the preparation of the core azobicyclo[7.3.1]tridecaenediyne moiety of the antitumor antibiotic dynemicin. The synthesis allows efficient production of the enediyne as a stable, compound in good yield from the adamantyl N-protected azabicyclo[7.3.1]tridecadiyne. The adamantyl protecting group is employed in the starting material, N-adamantyl dihydroquinoline or N-adamantyl 6-methoxy quinoline. Also disclosed are process for the synthesis of 3-hydroxy-6-methoxyquinoline and several N-substituted derivatives of azobicyclo[7.3.1]tridecaenediyne. Solid tumor and leukemia assays were performed on the analogs of dynemicin. The results suggest a method that these compounds will useful in treating certain types of leukemias and solid tumors. The disclosed synthesis provides a route to new dynemicin intermediates and analogs which will allow development of second and third generation dynemicins.
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- Short Synthesis of the Dynemicin Core Structure: Unusual Bridgehead Enolate Raectivity
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The dynemicin core azabicycloenediyne 2 is readily synthesized in five steps from the quinolines 9 or 13; the chemistry of the core enediyne is dominated by its ready enolization.
- Magnus, Philip,Parry, David,Iliadis, Theodore,Eisenbeis, Shane A.,Fairhurst, Robin A.
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p. 1543 - 1544
(2007/10/02)
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