JP2010504971A5 - - Google Patents

Info

Publication number

JP2010504971A5

JP2010504971A5 JP2009530403A JP2009530403A JP2010504971A5 JP 2010504971 A5 JP2010504971 A5 JP 2010504971A5 JP 2009530403 A JP2009530403 A JP 2009530403A JP 2009530403 A JP2009530403 A JP 2009530403A JP 2010504971 A5 JP2010504971 A5 JP 2010504971A5

Authority

JP

Japan

Prior art keywords

formulation

pharmaceutically acceptable

salt

argatroban

acceptable salt

Prior art date

2007-09-26

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Granted

Links

• Espacenet
• Global Dossier
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• 150000003839 salts Chemical class 0.000 claims description 42
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 21
• -1 2-carboxypiperidino group Chemical group 0.000 claims description 14
• 229910052757 nitrogen Inorganic materials 0.000 claims description 11
• 125000000217 alkyl group Chemical group 0.000 claims description 9
• 125000004432 carbon atom Chemical group C* 0.000 claims description 9
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
• 239000004475 Arginine Substances 0.000 claims description 4
• ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims description 4
• 125000001424 substituent group Chemical group 0.000 claims description 4
• NLLUNOTYWKPNRW-UHFFFAOYSA-N [N]C(O)=O Chemical group [N]C(O)=O NLLUNOTYWKPNRW-UHFFFAOYSA-N 0.000 claims description 3
• 238000000034 method Methods 0.000 claims description 2
• 239000000203 mixture Substances 0.000 claims 43
• 238000009472 formulation Methods 0.000 claims 28
• KXNPVXPOPUZYGB-XYVMCAHJSA-N argatroban Chemical compound OC(=O)[C@H]1C[C@H](C)CCN1C(=O)[C@H](CCCN=C(N)N)NS(=O)(=O)C1=CC=CC2=C1NC[C@H](C)C2 KXNPVXPOPUZYGB-XYVMCAHJSA-N 0.000 claims 19
• 229960003856 argatroban Drugs 0.000 claims 19
• 150000001875 compounds Chemical class 0.000 claims 14
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 12
• 229910052717 sulfur Inorganic materials 0.000 claims 12
• 150000001413 amino acids Chemical class 0.000 claims 11
• FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 claims 9
• 229930182817 methionine Natural products 0.000 claims 9
• 125000004434 sulfur atom Chemical group 0.000 claims 9
• UOQHWNPVNXSDDO-UHFFFAOYSA-N 3-bromoimidazo[1,2-a]pyridine-6-carbonitrile Chemical compound C1=CC(C#N)=CN2C(Br)=CN=C21 UOQHWNPVNXSDDO-UHFFFAOYSA-N 0.000 claims 8
• 229940099563 lactobionic acid Drugs 0.000 claims 8
• BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 7
• 229910052783 alkali metal Inorganic materials 0.000 claims 7
• DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims 6
• 239000000872 buffer Substances 0.000 claims 6
• 125000005842 heteroatom Chemical group 0.000 claims 6
• 125000000623 heterocyclic group Chemical group 0.000 claims 6
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 6
• 150000003863 ammonium salts Chemical class 0.000 claims 5
• 150000001340 alkali metals Chemical class 0.000 claims 4
• ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 claims 3
• 239000004471 Glycine Substances 0.000 claims 3
• ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 claims 3
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 3
• 239000001099 ammonium carbonate Substances 0.000 claims 3
• 239000007864 aqueous solution Substances 0.000 claims 3
• 125000004429 atom Chemical group 0.000 claims 3
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 3
• BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims 3
• 239000000470 constituent Substances 0.000 claims 3
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 3
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 3
• 229910052760 oxygen Inorganic materials 0.000 claims 3
• 239000001301 oxygen Substances 0.000 claims 3
• 239000011593 sulfur Substances 0.000 claims 3
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
• 239000008351 acetate buffer Substances 0.000 claims 2
• 229910000288 alkali metal carbonate Inorganic materials 0.000 claims 2
• 150000008041 alkali metal carbonates Chemical class 0.000 claims 2
• 235000012501 ammonium carbonate Nutrition 0.000 claims 2
• 239000007853 buffer solution Substances 0.000 claims 2
• 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 2
• 229940099584 lactobionate Drugs 0.000 claims 2
• JYTUSYBCFIZPBE-AMTLMPIISA-N lactobionic acid Chemical compound OC(=O)[C@H](O)[C@@H](O)[C@@H]([C@H](O)CO)O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O JYTUSYBCFIZPBE-AMTLMPIISA-N 0.000 claims 2
• 239000007788 liquid Substances 0.000 claims 2
• 229910000013 Ammonium bicarbonate Inorganic materials 0.000 claims 1
• KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims 1
• KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims 1
• 239000004472 Lysine Substances 0.000 claims 1
• OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 1
• 208000007536 Thrombosis Diseases 0.000 claims 1
• 230000002378 acidificating effect Effects 0.000 claims 1
• 239000013543 active substance Substances 0.000 claims 1
• 235000012538 ammonium bicarbonate Nutrition 0.000 claims 1
• 239000002585 base Substances 0.000 claims 1
• 239000002775 capsule Substances 0.000 claims 1
• 239000006071 cream Substances 0.000 claims 1
• 150000002016 disaccharides Chemical class 0.000 claims 1
• 239000002552 dosage form Substances 0.000 claims 1
• 238000001802 infusion Methods 0.000 claims 1
• 239000007972 injectable composition Substances 0.000 claims 1
• 229910052751 metal Inorganic materials 0.000 claims 1
• 239000002184 metal Substances 0.000 claims 1
• 150000002772 monosaccharides Chemical class 0.000 claims 1
• 239000003883 ointment base Substances 0.000 claims 1
• 229920001542 oligosaccharide Polymers 0.000 claims 1
• 150000002482 oligosaccharides Chemical class 0.000 claims 1
• 239000008194 pharmaceutical composition Substances 0.000 claims 1
• 150000005846 sugar alcohols Chemical class 0.000 claims 1
• 239000002511 suppository base Substances 0.000 claims 1
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
• 0 *C(C(CCCNC(N)=N)NS(*)(=O)=O)=O Chemical compound *C(C(CCCNC(N)=N)NS(*)(=O)=O)=O 0.000 description 1
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 229940124530 sulfonamide Drugs 0.000 description 1