US2010227882A1PendingUtilityA1

Clopidogrel salt and polymorphic forms thereof

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Assignee: SANOFI AVENTISPriority: Apr 20, 2004Filed: Jan 26, 2010Published: Sep 9, 2010
Est. expiryApr 20, 2024(expired)· nominal 20-yr term from priority
Inventors:Keith LorimerAlicia Tee Fuay Ng
A61P 9/10C07D 495/04A61P 9/00A61P 7/02
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Claims

Abstract

The invention relates to methyl(+)-(S)-α-(2-chlorophenyl)-6,7-dihydrothieno[3,2-C]pyridine-5(4H) acetate naphthalene-1,5-disulfonate or a polymorphic form and/or a hydrate and/or a solvate thereof, to pharmaceutical compositions containing the same, and to the method of use thereof for inhibiting platelet aggregation.

Claims

exact text as granted — not AI-modified
1 . Methyl(+)-(S)-α-(2-chlorophenyl)-6,7-dihydrothieno[3,2-C]pyridine-5(4H) acetate naphthalene-1,5-disulfonate, or a polymorphic form and/or a hydrate and/or a solvate thereof. 
   
   
       2 . Polymorphic Form A of methyl(+)-(S)-α-(2-chlorophenyl)-6,7-dihydrothieno[3,2-C]pyridine-5(4H) acetate naphthalene-1,5-disulfonate 1,4-dioxane according to  claim 1 . 
   
   
       3 . Polymorphic Form A of methyl(+)-(S)-α-(2-chlorophenyl)-6,7-dihydrothieno[3,2-C]pyridine-5(4H) acetate naphthalene-1,5-disulfonate 1,4-dioxane according to  claim 2  having an X-ray powder diffraction pattern with a peak at about 11.7 degrees two-theta. 
   
   
       4 . Polymorphic Form A of methyl(+)-(S)-α-(2-chlorophenyl)-6,7-dihydrothieno[3,2-C]pyridine-5(4H) acetate naphthalene-1,5-disulfonate 1,4-dioxane according to  claim 2  having an X-ray powder diffraction pattern with peaks at about 10.8, 11.7, and 13.0 degrees two-theta. 
   
   
       5 . Polymorphic Form A of methyl(+)-(S)-α-(2-chlorophenyl)-6,7-dihydrothieno[3,2-C]pyridine-5(4H) acetate naphthalene-1,5-disulfonate 1,4-dioxane according to  claim 2  having an FTIR spectrum with peaks at about 1249, 1452, 1760, 2848, 2955, 3090, and 3490 cm −1 . 
   
   
       6 . Polymorphic Form A of methyl(+)-(S)-α-(2-chlorophenyl)-6,7-dihydrothieno[3,2-C]pyridine-5(4H) acetate naphthalene-1,5-disulfonate 1,4-dioxane according to  claim 2  having a melting point of about 165° C. 
   
   
       7 . Polymorphic Form A of methyl(+)-(S)-α-(2-chlorophenyl)-6,7-dihydrothieno[3,2-C]pyridine-5(4H) acetate naphthalene-1,5-disulfonate 1,4-dioxane according to  claim 2  having an X-ray powder diffraction pattern substantially as depicted in  FIG. 1A . 
   
   
       8 . Polymorphic Form A of methyl(+)-(S)-α-(2-chlorophenyl)-6,7-dihydrothieno[3,2-C]pyridine-5(4H) acetate naphthalene-1,5-disulfonate 1,4-dioxane according to  claim 2  having an FTIR spectrum substantially as depicted in  FIG. 2 . 
   
   
       9 . Polymorphic Form B of methyl(+)-(S)-α-(2-chlorophenyl)-6,7-dihydrothieno[3,2-C]pyridine-5(4H) acetate naphthalene-1,5-disulfonate hydrate according to  claim 1 . 
   
   
       10 . Polymorphic Form B of methyl(+)-(S)-α-(2-chlorophenyl)-6,7-dihydrothieno[3,2-C]pyridine-5(4H) acetate naphthalene-1,5-disulfonate hydrate according to  claim 9  having an X-ray powder diffraction pattern with a peak at about 13.4 degrees two-theta. 
   
   
       11 . Polymorphic Form B of methyl(+)-(S)-α-(2-chlorophenyl)-6,7-dihydrothieno[3,2-C]pyridine-5(4H) acetate naphthalene-1,5-disulfonate hydrate according to  claim 9  having an FTIR spectrum with peaks at about 600, 663, 1096, 1156, 3557, and 3605 cm −1 . 
   
   
       12 . Polymorphic Form B of methyl(+)-(S)-α-(2-chlorophenyl)-6,7-dihydrothieno[3,2-C]pyridine-5(4H) acetate naphthalene-1,5-disulfonate hydrate according to  claim 9  having a melting point of about 218° C. 
   
   
       13 . Polymorphic Form B of methyl(+)-(S)-α-(2-chlorophenyl)-6,7-dihydrothieno[3,2-C]pyridine-5(4H) acetate naphthalene-1,5-disulfonate hydrate according to  claim 9  having an X-ray powder diffraction pattern substantially as depicted in  FIG. 1B . 
   
   
       14 . Polymorphic Form B of methyl(+)-(S)-α-(2-chlorophenyl)-6,7-dihydrothieno[3,2-c]pyridine-5(41-1) acetate naphthalene-1,5-disulfonate hydrate according to  claim 9  having an FTIR spectrum substantially as depicted in  FIG. 3 . 
   
   
       15 . Polymorphic Form C of methyl(+)-(S)-α-(2-chlorophenyl)-6,7-dihydrothieno[3,2-C]pyridine-5(4H) acetate naphthalene-1,5-disulfonate acetonitrile hydrate according to  claim 1 . 
   
   
       16 . Polymorphic Form C of methyl(+)-(S)-α-(2-chlorophenyl)-6,7-dihydrothieno[3,2-C]pyridine-5(4H) acetate naphthalene-1,5-disulfonate acetonitrile-hydrate according to  claim 15  having an X-ray powder diffraction pattern with a peak at about 8.7 degrees two-theta. 
   
   
       17 . Polymorphic Form C of methyl(+)-(S)-α-(2-chlorophenyl)-6,7-dihydrothieno[3,2-C]pyridine-5(4H) acetate naphthalene-1,5-disulfonate acetonitrile-hydrate according to  claim 15  having an X-ray powder diffraction pattern with peaks at about 8.7, 14.1, and 27.4 degrees two-theta. 
   
   
       18 . Polymorphic Form C of methyl(+)-(S)-α-(2-chlorophenyl)-6,7-dihydrothieno[3,2-C]pyridine-5(4H) acetate naphthalene-1,5-disulfonate acetonitrile-hydrate according to  claim 15  having an FTIR spectrum with peaks at about 529, 796, 1035, 1175, 1221, 1251, and 1759 cm −1 . 
   
   
       19 . Polymorphic Form C of methyl(+)-(S)-α-(2-chlorophenyl)-6,7-dihydrothieno[3,2-C]pyridine-5(4H) acetate naphthalene-1,5-disulfonate acetonitrile-hydrate according to  claim 15  having a melting point of about 228° C. 
   
   
       20 . Polymorphic Form C of methyl(+)-(S)-α-(2-chlorophenyl)-6,7-dihydrothieno[3,2-C]pyridine-5(4H) acetate naphthalene-1,5-disulfonate acetonitrile-hydrate according to  claim 15  having an X-ray powder diffraction pattern substantially as depicted in  FIG. 1C . 
   
   
       21 . Polymorphic Form C of methyl(+)-(S)-α-(2-chlorophenyl)-6,7-dihydrothieno[3,2-C]pyridine-5(4H) acetate naphthalene-1,5-disulfonate acetonitrile-hydrate according to  claim 15  having an FTIR spectrum substantially as depicted in  FIG. 4 . 
   
   
       22 . Polymorphic Form D of methyl(+)-(S)-α-(2-chlorophenyl)-6,7-dihydrothieno[3,2-e]pyridine-5(4H) acetate naphthalene-1,5-disulfonate hydrate according to  claim 1 . 
   
   
       23 . Polymorphic Form D of methyl(+)-(S)-α-(2-chlorophenyl)-6,7-dihydrothieno[3,2-C]pyridine-5(4H) acetate naphthalene-1,5-disulfonate hydrate according to  claim 22  having an X-ray powder diffraction pattern with a peak at about 24.1 degrees two-theta. 
   
   
       24 . Polymorphic Form D of methyl(+)-(S)-α-(2-chlorophenyl)-6,7-dihydrothieno[3,2-C]pyridine-5(4H) acetate naphthalene-1,5-disulfonate hydrate according to  claim 22  having an X-ray powder diffraction pattern with peaks at about 9.3 and 24.1 degrees two-theta. 
   
   
       25 . Polymorphic Form D of methyl(+)-(S)-α-(2-chlorophenyl)-6,7-dihydrothieno[3,2-C]pyridine-5(4H) acetate naphthalene-1,5-disulfonate hydrate according to  claim 22  having an FRIT spectrum with peaks at about 525, 711, 1026, 1170, 1243, and 1746-cm −1 . 
   
   
       26 . Polymorphic Form D of methyl(+)-(S)-α-(2-chlorophenyl)-6,7-dihydrothieno[3,2-C]pyridine-5(4H) acetate naphthalene-1,5-disulfonate hydrate according to  claim 22  having a melting point of about 228° C. 
   
   
       27 . Polymorphic Form D of methyl(+)-(S)-α-(2-chlorophenyl)-6,7-dihydrothieno[3,2-q]pyridine-5(4H) acetate naphthalene-1,5-disulfonate hydrate according to  claim 22  having an X-ray powder diffraction pattern substantially as depicted in  FIG. 1D . 
   
   
       28 . Polymorphic Form D of methyl(+)-(S)-α-(2-chlorophenyl)-6,7-dihydrothieno[3,2-C]pyridine-5(4H) acetate naphthalene-1,5-disulfonate hydrate according to  claim 22  having an FTIR spectrum substantially as depicted in  FIG. 5 . 
   
   
       29 . Polymorphic Form E of methyl(+)-(S)-α-(2-chlorophenyl)-6,7-dihydrothieno[3,2-C]pyridine-5(4H) acetate naphthalene-1,5-disulfonate hydrate according to  claim 1 . 
   
   
       30 . Polymorphic Form E of methyl(+)-(S)-α-(2-chlorophenyl)-6,7-dihydrothieno[3,2-C]pyridine-5(4H) acetate naphthalene-1,5-disulfonate hydrate according to  claim 29  having an X-ray powder diffraction pattern with a peak at about 26.4 degrees two-theta. 
   
   
       31 . Polymorphic Form E of methyl(+)-(S)-α-(2-chlorophenyl)-6,7-dihydrothieno[3,2-C]pyridine-5(4H) acetate naphthalene-1,5-disulfonate hydrate according to  claim 29  having an X-ray powder diffraction pattern with peaks at about 7.6, 11.0, 12.1, and 26.4 degrees two-theta. 
   
   
       32 . Polymorphic Form E of methyl(+)-(S)-α-(2-chlorophenyl)-6,7-dihydrothieno[3,2-C]pyridine-5(4H) acetate naphthalene-1,5-disulfonate hydrate according to  claim 29  having an FTIR spectrum with peaks at about 610, 764, 1026, 1196, 1224, and 1746 cm −1 . 
   
   
       33 . Polymorphic Form E of methyl(+)-(S)-α-(2-chlorophenyl)-6,7-dihydrothieno[3,2-C]pyridine-5(4H) acetate naphthalene-1,5-disulfonate hydrate according to  claim 29  having a melting point of about 224° C. 
   
   
       34 . Polymorphic Form E of methyl(+)-(S)-α-(2-chlorophenyl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H) acetate naphthalene-1,5-disulfonate hydrate according to  claim 29  having an X-ray powder diffraction pattern substantially as depicted in  FIG. 1E . 
   
   
       35 . Polymorphic Form E of methyl(+)-(S)-α-(2-chlorophenyl)-6,7-dihydrothieno[3,2-C]pyridine-5(4H) acetate naphthalene-1,5-disulfonate hydrate according to  claim 29  having an FTIR spectrum substantially as depicted in  FIG. 6 . 
   
   
       36 . Polymorphic Form F of methyl(+)-(S)-α-(2-chlorophenyl)-6,7-dihydrothieno[3,2-C]pyridine-5(4H) acetate naphthalene-1,5-disulfonate according to  claim 1 . 
   
   
       37 . Polymorphic Form F of methyl(+)-(S)-α-(2-chlorophenyl)-6,7-dihydrothieno[3,2-C]pyridine-5(4H) acetate naphthalene-1,5-disulfonate according to  claim 36  having an FTIR spectrum with peaks at about 565, 610, 764, 1028, 1751, and 2579 cm −1 . 
   
   
       38 . Polymorphic Form F of methyl(+)-(S)-α-(2-chlorophenyl)-6,7-dihydrothieno[3,2-C]pyridine-5(4H) acetate naphthalene-1,5-disulfonate according to  claim 36  haying an X-ray powder diffraction pattern substantially as depicted in  FIG. 1F . 
   
   
       39 . Polymorphic Form F of methyl(+)-(S)-α-(2-chlorophenyl)-6,7-dihydrothieno[3,2-C]pyridine-5(4H) acetate naphthalene-1,5-disulfonate according to  claim 36  having an FTIR spectrum substantially as depicted in  FIG. 7 . 
   
   
       40 . A pharmaceutical composition comprising a compound according to  claim 1  together with a pharmaceutically acceptable carrier, adjuvant, diluent, or vehicle. 
   
   
       41 . A method for inhibiting platelet aggregation which comprises administering to a patient in need thereof an effective amount of a compound according to  claim 1 . 
   
   
       42 . A method of reducing atherosclerotic events which comprises administering to a patient in need thereof an effective amount of a compound according to  claim 1 .

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