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Showing posts with label MOXIFLOXACIN. Show all posts
Showing posts with label MOXIFLOXACIN. Show all posts

Wednesday 17 June 2015

MOXIFLOXACIN





MOXIFLOXACINMoxifloxacin Structural Formulae V.1.svg





syn.......http://newdrugapprovals.org/2014/02/19/moxifloxacin-bay-12-8039/
1H NMR AND 13C IN DMSO.D6





13C ASSIGN


 



 


1H NMR ASSIGN

 

A practical synthesis of fluoroquinolone antibiotic moxifloxacin

Le Nguyen Thanh, Tran Huu Giap, To Hai Tung, Nguyen Anh Dung, Van Thi My Hue, Cao Thi Hue, Nguyen Thi Minh Hang, Nguyen Van Hung, Chau Van Minh
http://vjs.ac.vn/index.php/vjchem/article/view/0866-7144.2015-2e-012

206-208 oC;

1H-NMR
(500 MHz, DMSO-d6) δ (ppm): 8.62 (s, 1H, H-2);
7.60 (d, J = 14.5 Hz, 1H, H-5); 4.12-4.10 (m, 1H, H-
13); 3.98-3.94 (m, 1H); 3.88-3.86 (m, 1H); 3.54 (s,
3H, H-12); 3.37-3.23 (m, 3H); 2.88-2.86 (m, 1H);
2.54-2.51(m, 1H); 2.24 (m, 1H); 1.73- 1.59 (m, 3H);
1.41 (m, 1H); 1.21-1.17 (m, 1H); 1.13-1.08 (m, 1H);
1.02-0.96 (m, 1H); 0.89-0.84 (m, 1H).

13C-NMR
(125MHz, DMSO-d6) δ (ppm): 175.8; 165.9; 153.7;
149.9; 140.2; 137.3; 134.5; 116.4; 106.3; 106.1;
61.1; 58.5; 56.0; 52.1; 44.4; 40.6; 36.3; 22.9; 21.5;
9.6; 8.1. ESI-MS m/z: [M-H]-: 400.


 


COSY





  • Figure 13A: X-ray powder diffraction pattern of Moxifloxacin hydrochloride methylene dichloride solvate.
  • Figure 13B: Infrared spectrum of Moxifloxacin hydrochloride methylene dichloride solvate.
 

  • Figure 13C: 1H-NMR spectrum (DMSO-d6, TMS) of Moxifloxacin hydrochloride methylene dichloride solvate.
 

  • Figure 14A: X-ray powder diffraction pattern of anhydrous Moxifloxacin hydrochloride form IV.
  • Figure 14B: Infrared spectrum of anhydrous Moxifloxacin hydrochloride form IV.
 

  • Figure 15A: X-ray powder diffraction pattern of Moxifloxacin hydrochloride acetic acid solvate.
  • Figure 15B: Infrared spectrum of Moxifloxacin hydrochloride acetic acid solvate.
 

  • Figure 15C: 1H-NMR spectrum (DMSO-d6, TMS) of Moxifloxacin hydrochloride acetic acid solvate.
 
  • Figure 16A: X-ray powder diffraction pattern of Moxifloxacin hydrochloride nitromethane solvate.
  • Figure 16B: Infrared spectrum of Moxifloxacin hydrochloride nitromethane solvate.
 

syn.......http://newdrugapprovals.org/2014/02/19/moxifloxacin-bay-12-8039/
  • Figure 16C: 1H-NMR spectrum (DMSO-d6, TMS) of Moxifloxacin hydrochloride nitromethane solvate.
.
 


    Example 13
    preparation of Moxifloxacine hydrochloride anhydrous form IVExample13.aMoxifloxacine hydrochloride methylene dichloride solvate
  • [0100]
    5 g (12,5 mmol) Moxifloxacin were prepared according to EP 550903 and dissolved in 50 ml methylene dichloride at room temperature. To this solution 0,9 ml (1,2 equiv.) acetic acid and 2 ml (1,2 equiv.) trimethylchlorosilane were added under stirring. Immediately after addition of the chlorosilane the crystallization started. The suspension was stirred for about 30 min and the precipitate filtered off and dried under vacuum at room temperature to yield 6,3g (94,2%) of the 1:1 solvate of Moxifloxacine hydrochloride with methylene dichloride.
    1H-NMR (DMSO-d6): 0.8 - 0.95 (m, 1H), 0.95 - 1.3 (m, 3H), 1.6 - 1.9 (m, 4 H), 2.55 - 2.75 (m, 1H), 2.8 - 3.0 (m, 1H), 3.5 - 3.7 (m with Singlet at 3.6 ppm, 4H), 3.7 - 3.8 (m, 1H), 3.8 - 4.0 (m, 2H), 4.0 - 4.2 (m, 2H), 5.77 (s, 2H), 7.65 (d, J = 14 Hz, 1H), 8.66 (s, 1H), 8.95 (s, broad, 1H), 10.2 (s, broad, 1H), 15.1 (s, broad, 1H).
    The singlet at 5.77 ppm corresponds to about one mol methylene dichloride per mol of substance (see Figure 13C).
    The XRD pattern of the product is shown in Figure 13A and the infrared spectrum obtained is shown in Figure 13B.
    The Moxifloxacine hydrochloride solvate with methylene dichloride is not hygroscopic (no water uptake after 1 day at 33% relative humidity.
  • Example 13.bMoxifloxacine hydrochloride anhydrous form IV
  • [0101]
    2 g Moxifloxacine hydrochloride methylene dichloride solvate were dried in vacuum at 100°C for about 6 hours yielding 1,75 g of the desolvated anhydrous form IV of Moxifloxacine hydrochloride. The XRD pattern of the product is shown in Figure 14A and the infrared spectrum obtained is shown in Figure 14B.
  • Example 14preparation of Moxifloxacine hydrochloride solvate with acetic acidExample 14.a
  • [0102]
    3,0 g (7,47 mmol) moxifloxacin were prepared according to EP 550903 and dissolved in 30 ml acetic acid at room temperature. To this solution 2,0 ml (2,1 eq) trimethylchlorosilane were added under stirring. 30 minutes after addition of the chlorosilane the crystallization started. The suspension was stirred for about 3,5 hours and the precipitate filtered off washed with acetonitrile and dried under vacuum at room temperature to yield 3,21g (86,3%) of the 1:1 solvate of Moxifloxacine hydrochloride with acetic acid.
    1H-NMR (DMSO-d6): 0.8 - 0.95 (m, 1H), 0.95 - 1.3 (m, 3H), 1.6 - 1.9 (m, 4 H), 1.9 (s, 3H), 2.55 - 2.75 (m, 1H), 2.8 - 3.0 (m, 1H), 3.1 - 3.25 (m, 1H), 3.5 - 3.7 (m with Singlet at 3.6 ppm, 4H), 3.7 - 3.8 (m, 1H), 3.8 - 4.0 (m, 2H), 4.0 - 4.2 (m, 2H), 7.63 (d, J = 14 Hz, 1H), 8.65 (s, 1H), 9.1 (s, broad, 1H), 10.4 (s, broad, 1H), 12.7 (s, broad, 1H).
    The singlet at 1.9 ppm corresponds to about one mol acetic acid per mol of substance (see Figure 15C).
    The XRD pattern of the product is shown in Figure 15A and the infrared spectrum obtained is shown in Figure 15B.
  • Example 14.b
  • [0103]
    1,0 g (2,49 mmol) Moxifloxacin were prepared according to EP 550903 and dissolved in 5 ml acetic acid and 5 ml acetonitrile at room temperature. To this solution 0,38 ml (1,2 eq) trimethylchlorosilane were added under stirring.
    2 hours after addition of the chlorosilane the crystallization didn't start. To this solution 0,38 ml trimethylchlorosilane were once more added under stirring. The suspension was stored for about 17 hours at 4°C and the precipitate filtered off washed with acetonitrile and dried under vacuum at room temperature to yield 0,93g (75,0%) of the 1:1 solvate of Moxifloxacine hydrochloride with acetic acid.
  • Example 15preparation of Moxifloxacine hydrochloride solvate with nitromethane
  • [0104]
    0,5 g (1,25 mmol) Moxifloxacin were prepared according to EP 550903 and dissolved in 15 ml nitromethane at appr. 60°C. To this solution 0,14 ml (2 eq) acetic acid and (2 eq) ml trimethylchlorosilane were added under stirring. The suspension was stored for about 17 hours and the precipitate was filtered off, washed with acetone and dried under vacuum at room temperature to yield 0,55g (88,2%) of the 1:1 solvate of Moxifloxacine hydrochloride with nitromethane.
    1H-NMR (DMSO-d6): 0.8 - 0.95 (m, 1H), 0.95 - 1.3 (m, 3H), 1.6 - 1.9 (m, 4 H), 2.55 - 2.75 (m, 1H), 2.8 - 3.0 (m, 1H), 3.1 - 3.25 (m, 1H), 3.5 - 3.7 (m with Singlet at 3.6 ppm, 4H), 3.7 - 3.8 (m, 1H), 3.8 - 3.95 (m, 2H), 4.0 - 4.2 (m, 2H), 4.44 (s, 3H), 7.63 (d, J = 14 Hz, 1H), 8.65 (s, 1H), 9.0 (s, broad, 1H), 10.3 (s, broad, 1H), 15.1 (s, broad, 1H).
    The singlet at 4.44 ppm corresponds to about one mol nitromethane per mol of substance (see Figure 16C).
    The XRD pattern of the product is shown in Figure 16A and the infrared spectrum obtained is shown in Figure 16B..............http://www.google.nl/patents/EP2145890B1?cl=en

     moxifloxacin synthesis

    syn.......http://newdrugapprovals.org/2014/02/19/moxifloxacin-bay-12-8039/
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    Tonga ([ˈtoÅ‹a]; Tongan: PuleÊ»anga FakatuÊ»i Ê»o Tonga), officially the Kingdom of Tonga, is a Polynesian sovereign state and archipelago comprising 177 ...
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