BRPI0619425A2 - mesilato de pró-fármaco de levedopa, composição farmacêutica, método de preparar (2s)-2- amino-3-(3,4-diidróxi fenil) propanoato de mesilato de (2r)-2- fenil carbonilóxi propila e uso do referido composto - Google Patents

Info

Publication number

BRPI0619425A2

BRPI0619425A2 BRPI0619425-7A BRPI0619425A BRPI0619425A2 BR PI0619425 A2 BRPI0619425 A2 BR PI0619425A2 BR PI0619425 A BRPI0619425 A BR PI0619425A BR PI0619425 A2 BRPI0619425 A2 BR PI0619425A2

Authority

BR

Brazil

Prior art keywords

amino

propanoate

phenyl

mesylate

propyl

Prior art date

2005-12-05

Links

• Espacenet
• Global Dossier
• Discuss

• WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 title claims abstract description 155
• 238000000034 method Methods 0.000 title claims abstract description 63
• 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 54
• -1 (2r) -2-phenyl carbonyloxy propyl Chemical group 0.000 title claims description 199
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 title claims description 192
• 150000001875 compounds Chemical class 0.000 title claims description 42
• 239000000651 prodrug Substances 0.000 title description 72
• 229940002612 prodrug Drugs 0.000 title description 72
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 63
• 201000010099 disease Diseases 0.000 claims abstract description 39
• 208000035475 disorder Diseases 0.000 claims abstract description 24
• XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims abstract description 10
• 239000000203 mixture Substances 0.000 claims description 62
• 239000002904 solvent Substances 0.000 claims description 59
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 54
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 53
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 44
• 238000013270 controlled release Methods 0.000 claims description 36
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 33
• BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 33
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 27
• 208000018737 Parkinson disease Diseases 0.000 claims description 27
• 239000002253 acid Substances 0.000 claims description 26
• AKUWZLYXAADOTQ-DOMZBBRYSA-N [(2r)-1-[(2s)-2-amino-3-(3,4-dihydroxyphenyl)propanoyl]oxypropan-2-yl] benzoate Chemical compound C([C@H](N)C(=O)OC[C@@H](C)OC(=O)C=1C=CC=CC=1)C1=CC=C(O)C(O)=C1 AKUWZLYXAADOTQ-DOMZBBRYSA-N 0.000 claims description 25
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 25
• BFGJJGIBNQKBIQ-YLCXCWDSSA-N [(2r)-1-[(2s)-2-amino-3-(3,4-dihydroxyphenyl)propanoyl]oxypropan-2-yl] benzoate;methanesulfonic acid Chemical compound CS(O)(=O)=O.C([C@H](N)C(=O)OC[C@@H](C)OC(=O)C=1C=CC=CC=1)C1=CC=C(O)C(O)=C1 BFGJJGIBNQKBIQ-YLCXCWDSSA-N 0.000 claims description 22
• 229940098779 methanesulfonic acid Drugs 0.000 claims description 18
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 18
• 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 16
• 238000011282 treatment Methods 0.000 claims description 16
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 13
• 239000003937 drug carrier Substances 0.000 claims description 13
• 239000000843 powder Substances 0.000 claims description 13
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 12
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
• 150000003839 salts Chemical class 0.000 claims description 11
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 10
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• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 8
• 238000000113 differential scanning calorimetry Methods 0.000 claims description 8
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• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 6
• 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims description 6
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• LRVPEOXGGVAVBS-QAPCUYQASA-N [(2r)-1-[(2s)-3-(3,4-dihydroxyphenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]oxypropan-2-yl] benzoate Chemical compound C([C@@H](C(=O)OC[C@@H](C)OC(=O)C=1C=CC=CC=1)NC(=O)OC(C)(C)C)C1=CC=C(O)C(O)=C1 LRVPEOXGGVAVBS-QAPCUYQASA-N 0.000 claims description 4
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• 229910000028 potassium bicarbonate Inorganic materials 0.000 claims description 4
• TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 claims description 4
• 230000005855 radiation Effects 0.000 claims description 4
• 235000017557 sodium bicarbonate Nutrition 0.000 claims description 4
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• 238000001757 thermogravimetry curve Methods 0.000 claims description 4
• DZAUWHJDUNRCTF-UHFFFAOYSA-M 3-(3,4-dihydroxyphenyl)propanoate Chemical compound OC1=CC=C(CCC([O-])=O)C=C1O DZAUWHJDUNRCTF-UHFFFAOYSA-M 0.000 claims description 3
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• XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 3
• 230000007423 decrease Effects 0.000 claims description 3
• 238000010511 deprotection reaction Methods 0.000 claims description 3
• 239000000284 extract Substances 0.000 claims description 3
• WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 claims description 3
• 238000002844 melting Methods 0.000 claims description 3
• 230000008018 melting Effects 0.000 claims description 3
• 238000006386 neutralization reaction Methods 0.000 claims description 2
• YXKPMPXNTYMMKQ-UHFFFAOYSA-N propyl 2-amino-3-(3,4-dihydroxyphenyl)propanoate Chemical compound CCCOC(=O)C(N)CC1=CC=C(O)C(O)=C1 YXKPMPXNTYMMKQ-UHFFFAOYSA-N 0.000 claims 4
• 229940099362 Catechol O methyltransferase inhibitor Drugs 0.000 claims 2
• FWEPVBBXVAQJGQ-CWTRNNRKSA-N C[C@H](C[C@@](CC(C=C1)=CC(O)=C1O)(C(O)=O)N)OC(C1=CC=CC=C1)=O Chemical class C[C@H](C[C@@](CC(C=C1)=CC(O)=C1O)(C(O)=O)N)OC(C1=CC=CC=C1)=O FWEPVBBXVAQJGQ-CWTRNNRKSA-N 0.000 claims 1
• 230000000737 periodic effect Effects 0.000 claims 1
• AFVFQIVMOAPDHO-UHFFFAOYSA-M Methanesulfonate Chemical compound CS([O-])(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 abstract description 3
• 229950002475 mesilate Drugs 0.000 abstract description 3
• DKORSYDQYFVQNS-UHFFFAOYSA-N propyl methanesulfonate Chemical compound CCCOS(C)(=O)=O DKORSYDQYFVQNS-UHFFFAOYSA-N 0.000 abstract 1
• 239000003814 drug Substances 0.000 description 86
• 229940079593 drug Drugs 0.000 description 73
• WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 description 58
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