Crystal forms of saxagliptin and processes for preparing same

A crystalline compound of the structure

• in the form of
• (a) a hydrated HBr salt in the H2-1 form containing 2 equiv. H2O, characterized by unit cell parameters substantially equal to the following:
• Temperature ° C.
• at −50° C.
• at +22° C.
• a(Å)
• 11.120(1)
• 11.073(7)
• b(Å)
• 6.888(1)
• 6.877(7)
• c(Å)
• 12.993(1)
• 13.029(5) Å
• α°
• 90
• 90
• β°
• 94.60(1)
• 94.74(4)
• γ°
• 90
• 90
• Space group
• P21
• P21
• Molecules/asymmetric unit
• 1
• 1;
• or (b) a hydrated HBr salt in the H1-2 form containing 1 equiv. H2O, characterized by unit cell parameters substantially equal to the following:
• a=23.30(1) Å
• b=6.77(1) Å
• c=12.90(2) Å
• α=90°
• β=102.2(1)°
• γ=90°
• Space group C2
• Molecules/asymmetric unit 1
• wherein said crystalline form is at about 22° C.;
• or (c) a hydrated HI salt in the form H2-1 containing 2 equiv. H2O, characterized by unit cell parameters substantially equal to the following:
• a=11.267(1) Å
• b=7.006(4) Åc=13.22(2) Å
• α=90°
• β=93.96(9)°
• γ=90°
• Space group P21
• Molecules/asymmetric unit 1
• wherein said crystalline form is at about −20° C.;
• or (d) a hydrated ammonium sulfate salt in the H3-1 form containing 3 equiv. H2O, characterized by unit cell parameters substantially equal to the following:
• a=31.671(1) Å
• b=6.685(1) Å
• c=11.394(1) Å
• α=90°
• β=103.15(1)°
• γ=90°
• Space group C2
• Molecules/asymmetric unit 1
• wherein said crystalline form is at about −50° C.;
• or (e) a nitrate (NO3) salt in the N−1 form, characterized by unit cell parameters substantially equal to the following:
• a=20.615(1) Å
• b=25.214(1) Å
• c=7.034(1) Å
• α=90°
• β=90°
• γ=90°
• Space group P212121
• Molecules/asymmetric unit 2
• wherein said crystalline form is at about +22° C.;
• or (f) a hydrated benzoate salt in the H-1 form containing 1 equiv. H2O, characterized by unit cell parameters substantially equal to the following:
• Temperature ° C.
• at −40° C.
• at +22° C.
• a,(Å)
• 6.4065(2)
• 6.4316(2)
• b(Å)
• 16.9843(4)
• 17.0611(4)
• c(Å)
• 21.2504(5)
• 21.3010(5)
• α°
• 90
• 90
• β°
• 90
• 90
• γ°
• 90
• 90
• Space group
• P212121
• P212121
• Molecules/asymmetric unit
• 1
• 1;
• or (g) a hydrated R—H-tartrate salt in the H.5-1 form containing 0.5 equiv. of H2O characterized by unit cell parameters substantially equal to the following
• a=7.070(1) Å
• b=16.400(1) Å
• c=19.640(1) Å
• α=90°
• β=97.69(2)°
• γ=90°
• Space group P21
• Molecules/asymmetric unit 2
• wherein said crystalline form is at −173° C.;
• or (h) a hydrated fumarate salt in the H4-1 form containing 4 equiv. H2O, characterized by unit cell parameters substantially equal to the following:
• a=11.429(1) Å
• b=26.979(2) Å
• c=6.803(2) Å
• α=90°
• β=90.32(2)°
• γ=90°
• Space group P21
• Molecules/asymmetric unit 2
• wherein said crystalline form is at about +22° C.