WO2003079983A3 - Methods of preparing substituted tetracyclines with transition metal-based chemistries - Google Patents

Methods of preparing substituted tetracyclines with transition metal-based chemistries Download PDF

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Publication number
WO2003079983A3
WO2003079983A3 PCT/US2003/008323 US0308323W WO03079983A3 WO 2003079983 A3 WO2003079983 A3 WO 2003079983A3 US 0308323 W US0308323 W US 0308323W WO 03079983 A3 WO03079983 A3 WO 03079983A3
Authority
WO
WIPO (PCT)
Prior art keywords
tetracycline
substituted
compounds
transition metal
reactive
Prior art date
Application number
PCT/US2003/008323
Other languages
French (fr)
Other versions
WO2003079983A2 (en
Inventor
Mark L Nelson
Glen Rennie
Darrell J Koza
Original Assignee
Tufts College
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Tufts College filed Critical Tufts College
Priority to AU2003218242A priority Critical patent/AU2003218242A1/en
Publication of WO2003079983A2 publication Critical patent/WO2003079983A2/en
Publication of WO2003079983A3 publication Critical patent/WO2003079983A3/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
    • C07D295/182—Radicals derived from carboxylic acids
    • C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
    • C07C237/24—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring of the carbon skeleton
    • C07C237/26—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring of the carbon skeleton of a ring being part of a condensed ring system formed by at least four rings, e.g. tetracycline
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
    • C07D295/182—Radicals derived from carboxylic acids
    • C07D295/192—Radicals derived from carboxylic acids from aromatic carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/40—Ortho- or ortho- and peri-condensed systems containing four condensed rings
    • C07C2603/42—Ortho- or ortho- and peri-condensed systems containing four condensed rings containing only six-membered rings
    • C07C2603/44—Naphthacenes; Hydrogenated naphthacenes
    • C07C2603/46—1,4,4a,5,5a,6,11,12a- Octahydronaphthacenes, e.g. tetracyclines

Abstract

The present invention relates to novel chemistries which allow for heretofore unobtainable substituted tetracycline compounds which exhibit significant activity in tetracycline responsive states. The methods disclosed herein utilize reactive tetracycline-based precursor compounds, reactive organic substituent precursors and transition metal catalysts under conditions such that a tetracycline compound substituted with the desired organic substituent is formed. In one embodiment of the invention, a substituted tetracycline compound may be prepared by combining a reactive tetracycline-based precursor compound such as an arene tetracycline diazonium salt, and a reactive organic substituent precursor, e.g., alkenes, substituted alkenes, vinyl monomers, aromatics and heteroaromatics, in the presence of a transition metal catalyst, such as palladium chloride, under conditions such that a tetracycline compound substituted with the organic substituent is formed. Such compounds may optionally act as intermediates for making other compounds, e.g., hydrogenation of unsaturated groups on the substituent.
PCT/US2003/008323 2002-03-21 2003-03-18 Methods of preparing substituted tetracyclines with transition metal-based chemistries WO2003079983A2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2003218242A AU2003218242A1 (en) 2002-03-21 2003-03-18 Methods of preparing substituted tetracyclines with transition metal-based chemistries

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US36705002P 2002-03-21 2002-03-21
US60/367,050 2002-03-21

Publications (2)

Publication Number Publication Date
WO2003079983A2 WO2003079983A2 (en) 2003-10-02
WO2003079983A3 true WO2003079983A3 (en) 2004-11-11

Family

ID=28454832

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2003/008323 WO2003079983A2 (en) 2002-03-21 2003-03-18 Methods of preparing substituted tetracyclines with transition metal-based chemistries

Country Status (2)

Country Link
AU (1) AU2003218242A1 (en)
WO (1) WO2003079983A2 (en)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5010284B2 (en) 2004-01-15 2012-08-29 パラテック ファーマシューティカルズ インコーポレイテッド Aromatic A-ring derivatives of tetracycline compounds
EP2284164A3 (en) * 2004-10-25 2011-09-21 Paratek Pharmaceuticals, Inc. Substituted tetracycline compounds
WO2006047671A2 (en) 2004-10-25 2006-05-04 Paratek Pharmaceuticals, Inc. 4-aminotetracyclines and methods of use thereof
WO2007120913A2 (en) * 2006-04-17 2007-10-25 Teva Pharmaceutical Industries Ltd. Isolation of tetracycline derivatives

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20030055025A1 (en) * 2000-07-07 2003-03-20 Nelson Mark L. 7-substituted tetracycline compounds
US20030125348A1 (en) * 2000-07-07 2003-07-03 Nelson Mark L. 9-substituted minocycline compounds
US6617318B1 (en) * 1999-09-14 2003-09-09 Trustees Of Tufts College Methods of preparing substituted tetracyclines with transition metal-based chemistries

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6617318B1 (en) * 1999-09-14 2003-09-09 Trustees Of Tufts College Methods of preparing substituted tetracyclines with transition metal-based chemistries
US20030055025A1 (en) * 2000-07-07 2003-03-20 Nelson Mark L. 7-substituted tetracycline compounds
US20030125348A1 (en) * 2000-07-07 2003-07-03 Nelson Mark L. 9-substituted minocycline compounds

Also Published As

Publication number Publication date
WO2003079983A2 (en) 2003-10-02
AU2003218242A8 (en) 2003-10-08
AU2003218242A1 (en) 2003-10-08

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