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    Ῥαμάνθις Ἐρέβους
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    ORGANIKI SYN8ESH

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    35 views24 pages

    Organiki Syn8esh

    Uploaded by

    Ῥαμάνθις Ἐρέβους

    Copyright:

    Attribution Non-Commercial (BY-NC)
    Download as PDF, TXT or read online from Scribd
    Flag for inappropriate content
    of 24

    9/11/2011

    
    
     :

    --

    --

    9/11/2011

    9/11/2011





    
    
     (
    )
    
     -
     -
    .
    
    .

    
    
    
    
     ,

    9/11/2011

    1.


    C-X


    1. : SN2

    SN2
     : =k
    =k[RX][Nu]
    
    
    
    
     ,
    

    9/11/2011


    SN2

    R=CH3,

    =Cl, Br, I


    1.
    : SN1

    SN1
     : =k
    =k[RX]
    

    
    

     ,

    

    9/11/2011


    2. :


    2. : 2

    9/11/2011


    3.


    3.
    :

    9/11/2011


    4.

    Friedel-Crafts

    Friedel-Crafts


    4.

    9/11/2011


    4. :
    Friedel-Crafts


    4. :
    Friedel-Crafts

    () (84%)

    (62%)

    (56%)

    9/11/2011


    4. :
    Friedel-Crafts

    (97%)

    (82-85%)


    4. :
    Friedel-Crafts
    1

    2

    ( )

    10

    9/11/2011


    4. Friedel-Crafts
    )

    Sec-

    (32-36%)

    (64-68%)

    p--

    (24%)

    (14%)


    5.

    ) (-, RMgX)

    11

    9/11/2011


    5.
    ) (.. )
    )

    ::


    :
    15 ( 22)
    400
    400--900
    ( 19941994-2004).

    1 10000
    10000..

    ,
    .

    , ,
    .

    35 .

    12

    9/11/2011

    ::
    -

    10,000
    250

    1.5

    FDA

    IV


    100-300
    (Phase II)


    3-10,000 (Phase III)


    Phase I

    13

    9/11/2011

    - (Aspirin
    (Aspirin
    )
    400 ..:
    ..:
    (Willow)
    Willow) .
    O

    OH
    OH

    (Johann Buchner,
    Buchner, 1827
    1827))


    (Charles Gergardt
    Gergardt,, 1832
    1832))

    :
    , ,


    (Hermann Kolbe, 1859
    1859))

    - (Aspirin
    (Aspirin
    )
    Felix Hoffmann (1897)

    14

    9/11/2011

    - (Aspirin
    (Aspirin
    )
    1899: BAYER

    1930 Bayer


    1. Kolbe
    Kolbe--Schmidt

    H2SO4
    O
    OH

    2.

    OH

    OH

    OH

    90C, 20h

    15

    9/11/2011

    - : 35000tn
    35000tn/
    /
    : 100 /



    1.
    .

    .

    16

    9/11/2011



    1. :

    ZD2079



    2.

    :

    )
    ( , , )


    )



    17

    9/11/2011



    2. :

    Sidenafil (Viagra)


    ( )
    .

    2. :

    1997

    ,


    . ,
    (, 22) .

    18

    9/11/2011

    2. :

    sidenafil



    3.



    .

    :

    ( , ..)
    ( ,
    )

    19

    9/11/2011



    3. :

    To acyclovir
    GlaxoSmithKline
    . 1996 acyclovir
    40% (~1.25.
    )
    .

    (Burroughs
    (Burroughs-Wellcome)

    H Recordati

    R
    .
    ,


    .



    4.

    :

    20

    9/11/2011



    4. :

    N
    OH
    S
    O
    N

    ZD
    ZD--3638

    19931993-1997 Zeneca.
    To
    (
    (910/
    910/kg
    kg).
    ).

    :
    1475/
    1475/kg
    kg

    :
    789/
    789/kg
    kg

    21

    9/11/2011



    5.
    (throughput)
    (throughput) ( g, kg,
    tn) .


    ,

    , , ,
    , ,


    (.. )

    (.. )



    5. :
    HPLC

    Omeprazole
    ( )

    Esomeprazole
    (S-)




    1999


    6 .

    1993


    HPLC
    HPLC..

    22

    9/11/2011

    :
    40kg
    40kg omeprazole 500
    500g
    g esomeprasole
    6 3
    250250-500L
    500L
    430 HPLC
    (1 )
    ,
    500g
    500g esoprasole


    5kg
    5kg
    60000L
    60000L
    HPLC!!
    HPLC

    Esomeprazole
    (4.5%
    omeprazole)

    :



    .
    5kg esomeprasole 2 !

    Esoprazole
    (92%)

    23

    9/11/2011

    1. Mike Butters,David Catterick,Andrew Craig, Alan Curzons, David Dale, Adam


    Gillmore,Stuart P. Green, Ivan Marziano, Jon-Paul Sherlock, and Wesley White,
    Critical Assessment of Pharmaceutical Processes-A Rationale for
    Changing the Synthetic Route
    Chem. Rev. 2006, 106, 3002-3027
    2. Tony Y. Zhang
    Process Chemistry: The Science, Business, Logic, and Logistics
    Chem. Rev. 2006, 106, 2583-2595
    3. SciFinder Scholar ( site
    http://www.lib.ntua.gr/newsite/el/gindex.htm
    4. ISI Web of Science ( site )
    http://www.lib.ntua.gr/newsite/el/gindex.htm
    5. Scopus http://www.scopus.com/home.url
    6.
    http://www.heal-link.gr/journals/alphasearch.jsp

    24

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