BRPI0611476A2 - (s)-n-metilnaltrexona, processo para sua sìntese e seu uso farmacêutico - Google Patents

Info

Publication number

BRPI0611476A2

BRPI0611476A2 BRPI0611476-8A BRPI0611476A BRPI0611476A2 BR PI0611476 A2 BRPI0611476 A2 BR PI0611476A2 BR PI0611476 A BRPI0611476 A BR PI0611476A BR PI0611476 A2 BRPI0611476 A2 BR PI0611476A2

Authority

BR

Brazil

Prior art keywords

mntx

agent

opioid

composition

pharmaceutical composition

Prior art date

2005-05-25

Links

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• Global Dossier
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• 238000000034 method Methods 0.000 title claims abstract description 160
• 230000015572 biosynthetic process Effects 0.000 title abstract description 18
• 238000003786 synthesis reaction Methods 0.000 title abstract description 17
• 230000008569 process Effects 0.000 title abstract description 7
• 239000000203 mixture Substances 0.000 claims description 209
• 239000003814 drug Substances 0.000 claims description 169
• -1 burprenorine Chemical compound 0.000 claims description 101
• 229940124597 therapeutic agent Drugs 0.000 claims description 92
• 239000003795 chemical substances by application Substances 0.000 claims description 80
• 230000000694 effects Effects 0.000 claims description 72
• 150000001875 compounds Chemical class 0.000 claims description 68
• 239000002904 solvent Substances 0.000 claims description 67
• 206010012735 Diarrhoea Diseases 0.000 claims description 60
• 208000002193 Pain Diseases 0.000 claims description 59
• 238000011282 treatment Methods 0.000 claims description 57
• 230000036407 pain Effects 0.000 claims description 56
• 239000008194 pharmaceutical composition Substances 0.000 claims description 50
• 238000009472 formulation Methods 0.000 claims description 42
• BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 claims description 40
• 238000004128 high performance liquid chromatography Methods 0.000 claims description 37
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 33
• 206010061218 Inflammation Diseases 0.000 claims description 31
• 230000004054 inflammatory process Effects 0.000 claims description 31
• 230000002093 peripheral effect Effects 0.000 claims description 31
• 239000007787 solid Substances 0.000 claims description 31
• 238000006243 chemical reaction Methods 0.000 claims description 30
• 238000004587 chromatography analysis Methods 0.000 claims description 29
• UQCNKQCJZOAFTQ-ISWURRPUSA-N Oxymorphone Chemical compound O([C@H]1C(CC[C@]23O)=O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O UQCNKQCJZOAFTQ-ISWURRPUSA-N 0.000 claims description 28
• 229960005118 oxymorphone Drugs 0.000 claims description 26
• 239000003402 opiate agonist Substances 0.000 claims description 24
• CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 22
• 208000035154 Hyperesthesia Diseases 0.000 claims description 22
• 208000004454 Hyperalgesia Diseases 0.000 claims description 21
• SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 21
• 229960005181 morphine Drugs 0.000 claims description 20
• 238000000746 purification Methods 0.000 claims description 20
• 238000013268 sustained release Methods 0.000 claims description 20
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• 150000004820 halides Chemical class 0.000 claims description 19
• 230000002401 inhibitory effect Effects 0.000 claims description 19
• 239000003242 anti bacterial agent Substances 0.000 claims description 18
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• 238000001953 recrystallisation Methods 0.000 claims description 18
• 229910052757 nitrogen Inorganic materials 0.000 claims description 17
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• 239000003793 antidiarrheal agent Substances 0.000 claims description 16
• XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical group I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 16
• 238000004519 manufacturing process Methods 0.000 claims description 15
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• 239000000829 suppository Substances 0.000 claims description 14
• IFGIYSGOEZJNBE-KNLJMPJLSA-N (4r,4as,7ar,12bs)-3-(cyclopropylmethyl)-4a,9-dihydroxy-3-methyl-2,4,5,6,7a,13-hexahydro-1h-4,12-methanobenzofuro[3,2-e]isoquinoline-3-ium-7-one;bromide Chemical compound [Br-].C[N+]1([C@@H]2CC=3C4=C(C(=CC=3)O)O[C@@H]3[C@]4([C@@]2(O)CCC3=O)CC1)CC1CC1 IFGIYSGOEZJNBE-KNLJMPJLSA-N 0.000 claims description 13
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• RDOIQAHITMMDAJ-UHFFFAOYSA-N loperamide Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(C(=O)N(C)C)CCN(CC1)CCC1(O)C1=CC=C(Cl)C=C1 RDOIQAHITMMDAJ-UHFFFAOYSA-N 0.000 claims description 13
• 229960001571 loperamide Drugs 0.000 claims description 13
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• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 12
• 125000000129 anionic group Chemical group 0.000 claims description 12
• 229940088710 antibiotic agent Drugs 0.000 claims description 12
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• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 11
• RKUNBYITZUJHSG-UHFFFAOYSA-N Hyosciamin-hydrochlorid Natural products CN1C(C2)CCC1CC2OC(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-UHFFFAOYSA-N 0.000 claims description 11
• JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims description 11
• 230000005176 gastrointestinal motility Effects 0.000 claims description 11
• JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 claims description 11
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• 229910052797 bismuth Inorganic materials 0.000 claims description 10
• JHKJQWFHNIOUKY-UHFFFAOYSA-N iodomethylcyclopropane Chemical compound ICC1CC1 JHKJQWFHNIOUKY-UHFFFAOYSA-N 0.000 claims description 10
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• 229940011051 isopropyl acetate Drugs 0.000 claims description 10
• GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims description 10
• HYPPXZBJBPSRLK-UHFFFAOYSA-N diphenoxylate Chemical compound C1CC(C(=O)OCC)(C=2C=CC=CC=2)CCN1CCC(C#N)(C=1C=CC=CC=1)C1=CC=CC=C1 HYPPXZBJBPSRLK-UHFFFAOYSA-N 0.000 claims description 9
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• 238000007455 ileostomy Methods 0.000 claims description 9
• 230000009885 systemic effect Effects 0.000 claims description 9
• DEQANNDTNATYII-OULOTJBUSA-N (4r,7s,10s,13r,16s,19r)-10-(4-aminobutyl)-19-[[(2r)-2-amino-3-phenylpropanoyl]amino]-16-benzyl-n-[(2r,3r)-1,3-dihydroxybutan-2-yl]-7-[(1r)-1-hydroxyethyl]-13-(1h-indol-3-ylmethyl)-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carboxa Chemical compound C([C@@H](N)C(=O)N[C@H]1CSSC[C@H](NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCCCN)NC(=O)[C@@H](CC=2C3=CC=CC=C3NC=2)NC(=O)[C@H](CC=2C=CC=CC=2)NC1=O)C(=O)N[C@H](CO)[C@H](O)C)C1=CC=CC=C1 DEQANNDTNATYII-OULOTJBUSA-N 0.000 claims description 8
• 108010016076 Octreotide Proteins 0.000 claims description 8
• 229940069428 antacid Drugs 0.000 claims description 8
• 239000003159 antacid agent Substances 0.000 claims description 8
• 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 claims description 8
• 229910019142 PO4 Inorganic materials 0.000 claims description 7
• KBOPZPXVLCULAV-UHFFFAOYSA-N mesalamine Chemical compound NC1=CC=C(O)C(C(O)=O)=C1 KBOPZPXVLCULAV-UHFFFAOYSA-N 0.000 claims description 7
• 238000004806 packaging method and process Methods 0.000 claims description 7
• 241000894007 species Species 0.000 claims description 7
• 239000005526 vasoconstrictor agent Substances 0.000 claims description 7
• 229930003347 Atropine Natural products 0.000 claims description 6
• XADCESSVHJOZHK-UHFFFAOYSA-N Meperidine Chemical compound C=1C=CC=CC=1C1(C(=O)OCC)CCN(C)CC1 XADCESSVHJOZHK-UHFFFAOYSA-N 0.000 claims description 6
• 239000003429 antifungal agent Substances 0.000 claims description 6
• 239000004599 antimicrobial Substances 0.000 claims description 6
• 239000003096 antiparasitic agent Substances 0.000 claims description 6
• RKUNBYITZUJHSG-SPUOUPEWSA-N atropine Chemical compound O([C@H]1C[C@H]2CC[C@@H](C1)N2C)C(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-SPUOUPEWSA-N 0.000 claims description 6
• 229960000396 atropine Drugs 0.000 claims description 6
• 239000013078 crystal Substances 0.000 claims description 6
• 239000003937 drug carrier Substances 0.000 claims description 6
• 239000003589 local anesthetic agent Substances 0.000 claims description 6
• 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 claims description 6
• 229960002700 octreotide Drugs 0.000 claims description 6
• 229960000482 pethidine Drugs 0.000 claims description 6
• 230000006433 tumor necrosis factor production Effects 0.000 claims description 6
• RKUNBYITZUJHSG-FXUDXRNXSA-N (S)-atropine Chemical compound C1([C@@H](CO)C(=O)O[C@H]2C[C@H]3CC[C@@H](C2)N3C)=CC=CC=C1 RKUNBYITZUJHSG-FXUDXRNXSA-N 0.000 claims description 5
• HLMSIZPQBSYUNL-IPOQPSJVSA-N Noroxymorphone Chemical group O=C([C@@H]1O2)CC[C@@]3(O)[C@H]4CC5=CC=C(O)C2=C5[C@@]13CCN4 HLMSIZPQBSYUNL-IPOQPSJVSA-N 0.000 claims description 5
• 229940125687 antiparasitic agent Drugs 0.000 claims description 5
• 239000003904 antiprotozoal agent Substances 0.000 claims description 5
• 229960004645 bismuth subcitrate Drugs 0.000 claims description 5
• ZQUAVILLCXTKTF-UHFFFAOYSA-H bismuth;tripotassium;2-hydroxypropane-1,2,3-tricarboxylate Chemical compound [K+].[K+].[K+].[Bi+3].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O ZQUAVILLCXTKTF-UHFFFAOYSA-H 0.000 claims description 5
• AMTWCFIAVKBGOD-UHFFFAOYSA-N dioxosilane;methoxy-dimethyl-trimethylsilyloxysilane Chemical compound O=[Si]=O.CO[Si](C)(C)O[Si](C)(C)C AMTWCFIAVKBGOD-UHFFFAOYSA-N 0.000 claims description 5
• 230000007661 gastrointestinal function Effects 0.000 claims description 5
• 229930005342 hyoscyamine Natural products 0.000 claims description 5
• 229960003210 hyoscyamine Drugs 0.000 claims description 5
• NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 5
• 239000010452 phosphate Substances 0.000 claims description 5
• 230000009467 reduction Effects 0.000 claims description 5
• 229940083037 simethicone Drugs 0.000 claims description 5
• 238000011200 topical administration Methods 0.000 claims description 5
• 229910002651 NO3 Inorganic materials 0.000 claims description 4
• NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 4
• 239000008896 Opium Substances 0.000 claims description 4
• QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 4
• QJJXYPPXXYFBGM-LFZNUXCKSA-N Tacrolimus Chemical compound C1C[C@@H](O)[C@H](OC)C[C@@H]1\C=C(/C)[C@@H]1[C@H](C)[C@@H](O)CC(=O)[C@H](CC=C)/C=C(C)/C[C@H](C)C[C@H](OC)[C@H]([C@H](C[C@H]2C)OC)O[C@@]2(O)C(=O)C(=O)N2CCCC[C@H]2C(=O)O1 QJJXYPPXXYFBGM-LFZNUXCKSA-N 0.000 claims description 4
• 150000003797 alkaloid derivatives Chemical class 0.000 claims description 4
• WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 claims description 4
• 229940024545 aluminum hydroxide Drugs 0.000 claims description 4
• 229960002512 anileridine Drugs 0.000 claims description 4
• LKYQLAWMNBFNJT-UHFFFAOYSA-N anileridine Chemical compound C1CC(C(=O)OCC)(C=2C=CC=CC=2)CCN1CCC1=CC=C(N)C=C1 LKYQLAWMNBFNJT-UHFFFAOYSA-N 0.000 claims description 4
• JHLHNYVMZCADTC-LOSJGSFVSA-N asimadoline Chemical compound C([C@@H](N(C)C(=O)C(C=1C=CC=CC=1)C=1C=CC=CC=1)C=1C=CC=CC=1)N1CC[C@H](O)C1 JHLHNYVMZCADTC-LOSJGSFVSA-N 0.000 claims description 4
• 229950002202 asimadoline Drugs 0.000 claims description 4
• 150000001649 bromium compounds Chemical group 0.000 claims description 4
• 229960001113 butorphanol Drugs 0.000 claims description 4
• IFKLAQQSCNILHL-QHAWAJNXSA-N butorphanol Chemical compound N1([C@@H]2CC3=CC=C(C=C3[C@@]3([C@]2(CCCC3)O)CC1)O)CC1CCC1 IFKLAQQSCNILHL-QHAWAJNXSA-N 0.000 claims description 4
• DCSUBABJRXZOMT-IRLDBZIGSA-N cisapride Chemical compound C([C@@H]([C@@H](CC1)NC(=O)C=2C(=CC(N)=C(Cl)C=2)OC)OC)N1CCCOC1=CC=C(F)C=C1 DCSUBABJRXZOMT-IRLDBZIGSA-N 0.000 claims description 4
• 229960005132 cisapride Drugs 0.000 claims description 4
• DCSUBABJRXZOMT-UHFFFAOYSA-N cisapride Natural products C1CC(NC(=O)C=2C(=CC(N)=C(Cl)C=2)OC)C(OC)CN1CCCOC1=CC=C(F)C=C1 DCSUBABJRXZOMT-UHFFFAOYSA-N 0.000 claims description 4
• XYYVYLMBEZUESM-UHFFFAOYSA-N dihydrocodeine Natural products C1C(N(CCC234)C)C2C=CC(=O)C3OC2=C4C1=CC=C2OC XYYVYLMBEZUESM-UHFFFAOYSA-N 0.000 claims description 4
• 229960002428 fentanyl Drugs 0.000 claims description 4
• 150000002500 ions Chemical class 0.000 claims description 4
• MJIHNNLFOKEZEW-UHFFFAOYSA-N lansoprazole Chemical compound CC1=C(OCC(F)(F)F)C=CN=C1CS(=O)C1=NC2=CC=CC=C2N1 MJIHNNLFOKEZEW-UHFFFAOYSA-N 0.000 claims description 4
• ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 claims description 4
• 239000001095 magnesium carbonate Substances 0.000 claims description 4
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• VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 claims description 4
• 239000000347 magnesium hydroxide Substances 0.000 claims description 4
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• QQBDLJCYGRGAKP-FOCLMDBBSA-N olsalazine Chemical compound C1=C(O)C(C(=O)O)=CC(\N=N\C=2C=C(C(O)=CC=2)C(O)=O)=C1 QQBDLJCYGRGAKP-FOCLMDBBSA-N 0.000 claims description 4
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• NCEXYHBECQHGNR-QZQOTICOSA-N sulfasalazine Chemical compound C1=C(O)C(C(=O)O)=CC(\N=N\C=2C=CC(=CC=2)S(=O)(=O)NC=2N=CC=CC=2)=C1 NCEXYHBECQHGNR-QZQOTICOSA-N 0.000 claims description 4
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• KKMOSYLWYLMHAL-UHFFFAOYSA-N 2-bromo-6-nitroaniline Chemical compound NC1=C(Br)C=CC=C1[N+]([O-])=O KKMOSYLWYLMHAL-UHFFFAOYSA-N 0.000 claims description 3
• USSIQXCVUWKGNF-UHFFFAOYSA-N 6-(dimethylamino)-4,4-diphenylheptan-3-one Chemical compound C=1C=CC=CC=1C(CC(C)N(C)C)(C(=O)CC)C1=CC=CC=C1 USSIQXCVUWKGNF-UHFFFAOYSA-N 0.000 claims description 3
• GVGLGOZIDCSQPN-PVHGPHFFSA-N Heroin Chemical compound O([C@H]1[C@H](C=C[C@H]23)OC(C)=O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4OC(C)=O GVGLGOZIDCSQPN-PVHGPHFFSA-N 0.000 claims description 3
• UETNIIAIRMUTSM-UHFFFAOYSA-N Jacareubin Natural products CC1(C)OC2=CC3Oc4c(O)c(O)ccc4C(=O)C3C(=C2C=C1)O UETNIIAIRMUTSM-UHFFFAOYSA-N 0.000 claims description 3
• GNJCUHZOSOYIEC-GAROZEBRSA-N Morphine-6-glucuronide Chemical compound O([C@H]1C=C[C@H]2[C@H]3CC=4C5=C(C(=CC=4)O)O[C@@H]1[C@]52CCN3C)[C@@H]1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O GNJCUHZOSOYIEC-GAROZEBRSA-N 0.000 claims description 3
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• SULICOHAQXOMED-YDXPQRMKSA-H dibismuth;(2r,3r)-2,3-dihydroxybutanedioate Chemical compound [Bi+3].[Bi+3].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O.[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O.[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O SULICOHAQXOMED-YDXPQRMKSA-H 0.000 claims description 3
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