Formulations of Tetrahydropyridine Antiplatelet Agents for Parenteral or Oral Administration

A pharmaceutical composition comprising an oil-in-water emulsion comprising an oil phase and an aqueous phase wherein the emulsion comprises a surfactant that is soluble in the oil phase and/or the aqueous phase,

• wherein the oil phase comprises the free base or a pharmaceutically acceptable salt thereof of a compound of Formula I,
• wherein
• R1 represents a hydrogen atom;
• an alkyl group having from 1 to 10 carbon atoms;
• a halogen atom;
• a haloalkyl group having from 1 to 10 carbon atoms and at least one halogen atom;
• a hydroxy group;
• an alkoxy group having from 1 to 10 carbon atoms;
• a haloalkoxy group having from 1 to 10 carbon atoms and at least one halogen atom;
• an alkylthio group having from 1 to 10 carbon atoms;
• a haloalkylthio group having from 1 to 10 carbon atoms and at least one halogen atom;
• an amino group;
• an alkanoyl group having from 1 to 10 carbon atoms;
• a substituted alkanoyl group which has from 2 to 10 carbon atoms and which is substituted by at least one substituent selected from the group consisting of halogen atoms, hydroxy groups, alkoxy groups having from 1 to 10 carbon atoms, and cyano groups;
• an alkanoyloxy group having from 1 to 10 carbon atoms;
• a substituted alkanoyloxy group which has from 2 to 10 carbon atoms and which is substituted by at least one substituent selected from the group consisting of halogen atoms, hydroxy groups, alkoxy groups having from 1 to 10 carbon atoms, and cyano groups;
• a haloalkanoyl group having from 2 to 10 carbon atoms and at least one halogen atom;
• a carboxy group;
• an alkoxycarbonyl group having from 2 to 10 carbon atoms;
• a substituted alkoxycarbonyl group which has from 2 to 10 carbon atoms and which is substituted by at least one substituent selected from the group consisting of halogen atoms, hydroxy groups, alkoxy groups having from 1 to 10 carbon atoms, and cyano groups;
• a carbamoyl group having 1 to 10 carbon atoms;
• a cyano group;
• a nitro group;
• an alkane-sulfonyl group having from 1 to 10 carbon atoms;
• a haloalkanesulfonyl group having from 1 to 10 carbon atoms and at least one halogen atom, or a sulfamoyl group;
• R2 represents hydrogen;
• an alkanoyl group having from 1 to 10 carbon atoms;
• a substituted alkanoyl group which has from 2 to 10 carbon atoms and which is substituted by at least one substituent selected from the group consisting of halogen atoms, hydroxy groups, alkoxy groups having from 1 to 10 carbon atoms, and cyano groups;
• an alkenoyl group having from 3 to 10 carbon atoms;
• a substituted alkenoyl group which has from 3 to 10 carbon atoms and which is substituted by at least one substituent selected from the group consisting of halogen atoms, hydroxy groups, alkoxy groups having from 1 to 10 carbon atoms, and cyano groups;
• an alkanoyloxy group having from 1 to 10 carbon atoms;
• a substituted alkanoyloxy group which has from 2 to 10 carbon atoms and which is substituted by at least one substituent selected from the group consisting of halogen atoms, hydroxy groups, alkoxy groups having from 1 to 10 carbon atoms, and cyano groups;
• an alkoxy carbonyl group having from 1 to 10 carbon atoms;
• a substituted alkoxycarbonyl group which is substituted by at least one substituent selected from the group consisting of halogen atoms, hydroxy groups, alkoxy groups having from 1 to 10 carbon atoms, and cyano groups;
• a substituted benzoyl group having at least one substituent selected from the group consisting of alkyl groups having from 1 to 10 carbon atoms, halogen atoms, and alkoxy groups having 1 to 10 carbon atoms;
• R3 represents a hydrogen atom;
• a hydroxy group;
• an alkoxy group having from 1 to 10 carbon atoms;
• a substituted alkoxy group which has from 1 to 10 carbon atoms and which is substituted by at least one substituent selected from the group consisting of alkoxy groups having 1 to 10 carbon atoms, alkanoyloxy groups having from 1 to 10 carbon atoms, and arylcarbonyloxy groups in which the aryl moiety has from 6 to 10 carbon atoms in a carbocyclic ring, which is unsubstituted or substituted as defined in R1;
• an aralkyloxy group in which the aralkyl moiety is an alkyl group having from 1 to 10 carbon atoms which is substituted by at least one aryl group having 6 to 10 carbon atoms in a carbocyclic ring;
• an alkanoyloxy group having from 1 to 18 carbon atoms;
• an alkenyloxy group having from 3 to 10 carbon atoms;
• an arylcarbonyloxy group in which the aryl part has from 6 to 10 carbon atoms in a carbocyclic ring, which is unsubstituted or substituted as defined in R1;
• an alkoxycarbonyloxy group having from 2 to 10 carbon atoms;
• an aralkyloxycarbonyloxy group in which the aralkyl part is an alkyl group having from 1 to 10 carbon atoms and which is substituted by at least one aryl group having from 6 to 10 carbon atoms in a carbocyclic ring, which is unsubstituted or substituted as defined in R1;
• or a group having the formula —NRaRb,
• in which Ra and Rb are independently selected from the group consisting of hydrogen atoms;
• alkyl groups having from 1 to 10 carbon atoms;
• substituted alkyl groups which have from 1 to 10 carbon atoms and which are substituted by at least one substituent selected from the group consisting of alkoxy groups having 1 to 10 carbon atoms, alkanoyloxy groups having from 1 to 10 carbon atoms, and arylcarbonyloxy groups in which the aryl moiety has from 6 to 10 carbon atoms in a carbocyclic ring, which is unsubstituted or substituted as defined in R1;
• an aralkylamino group in which the aralkyl part is as define in R2;
• an alkanoylamino group having from 1 to 18 carbon atoms;
• an alkenoylamino group having from 3 to 10 carbon atoms;
• a cycloalkyl-carbonylamino group having from 4 to 10 carbon atoms;
• an arylcarbonylamino group in which the aryl is an aryl group having from 6 to 10 carbon atoms in a carbocyclic ring, which is unsubstituted or substituted as defined in R1;
• an alkoxycarbonylamino group having from 2 to 10 carbon atoms;
• an aralkyloxycarbonylamino group in which the aralkyl part is as defined in R2;
• Y represents an —NH— group, or an oxygen or sulfur atom;
• and
• n is an integer from 1 to 5, and, when n is an integer from 2 to 5, the group represented by R1 may be the same or different from each other;
• wherein the composition is in a form suitable for parenteral or oral administration.