AU2002329634B2 - Sugar derivatives of hydromorphone, dihydromorphine and dihydroisomorphine, compositions thereof and uses for treating or preventing pain - Google Patents

Info

Publication number

AU2002329634B2

AU2002329634B2 AU2002329634A AU2002329634A AU2002329634B2 AU 2002329634 B2 AU2002329634 B2 AU 2002329634B2 AU 2002329634 A AU2002329634 A AU 2002329634A AU 2002329634 A AU2002329634 A AU 2002329634A AU 2002329634 B2 AU2002329634 B2 AU 2002329634B2

Authority

AU

Australia

Prior art keywords

hydromorphone

dihydromorphine

pharmaceutically acceptable

glucuronide

dihydroisomorphine

Prior art date

2001-07-27

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.)

Ceased

Links

• Espacenet
• Global Dossier
• Discuss

• 208000002193 Pain Diseases 0.000 title claims abstract description 43
• 230000036407 pain Effects 0.000 title claims abstract description 38
• 239000000203 mixture Substances 0.000 title claims description 46
• IJVCSMSMFSCRME-KBQPJGBKSA-N Dihydromorphine Chemical compound O([C@H]1[C@H](CC[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O IJVCSMSMFSCRME-KBQPJGBKSA-N 0.000 title abstract description 34
• IJVCSMSMFSCRME-NOSXKOESSA-N (4r,4ar,7r,7ar,12bs)-3-methyl-2,4,4a,5,6,7,7a,13-octahydro-1h-4,12-methanobenzofuro[3,2-e]isoquinoline-7,9-diol Chemical compound O([C@H]1[C@@H](CC[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O IJVCSMSMFSCRME-NOSXKOESSA-N 0.000 title abstract description 16
• WVLOADHCBXTIJK-YNHQPCIGSA-N hydromorphone Chemical class O([C@H]1C(CC[C@H]23)=O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O WVLOADHCBXTIJK-YNHQPCIGSA-N 0.000 title description 25
• 235000000346 sugar Nutrition 0.000 title description 10
• 238000000034 method Methods 0.000 claims abstract description 39
• 150000003839 salts Chemical class 0.000 claims abstract description 32
• 150000001875 compounds Chemical class 0.000 claims description 86
• 239000003981 vehicle Substances 0.000 claims description 12
• MJAROVOYFMVSGP-DQSNCFNGSA-N (3r,4s,5s,6r)-2-[[(4r,4ar,7s,7ar,12bs)-7-hydroxy-3-methyl-2,4,4a,5,6,7,7a,13-octahydro-1h-4,12-methanobenzofuro[3,2-e]isoquinoline-9-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound O([C@@H]1[C@]23CCN([C@H](C4)[C@@H]3CC[C@@H]1O)C)C1=C2C4=CC=C1OC1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O MJAROVOYFMVSGP-DQSNCFNGSA-N 0.000 claims description 7
• 239000003937 drug carrier Substances 0.000 claims description 6
• FGEXYJIHXVZJMD-OHEXMFCKSA-N (3r,4s,5s,6r)-2-[[(4r,4ar,7s,7ar,12bs)-9-hydroxy-3-methyl-2,4,4a,5,6,7,7a,13-octahydro-1h-4,12-methanobenzofuro[3,2-e]isoquinoline-7-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound O([C@H]1CC[C@H]2[C@H]3CC=4C5=C(C(=CC=4)O)O[C@@H]1[C@]52CCN3C)C1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O FGEXYJIHXVZJMD-OHEXMFCKSA-N 0.000 claims description 5
• LAZTZBKWNKFJLP-AUTNIQMOSA-N (4r,4ar,7ar,12bs)-3-methyl-9-[(3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,2,4,4a,5,6,7a,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinoline-7-one Chemical compound O([C@@H]1[C@]23CCN([C@H](C4)[C@@H]3CCC1=O)C)C1=C2C4=CC=C1OC1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O LAZTZBKWNKFJLP-AUTNIQMOSA-N 0.000 claims description 5
• -1 glucuronide derivatives of hydromorphone Chemical class 0.000 abstract description 60
• 229930182478 glucoside Natural products 0.000 abstract description 9
• 150000008131 glucosides Chemical class 0.000 abstract description 8
• 229930182480 glucuronide Natural products 0.000 abstract description 7
• 239000008194 pharmaceutical composition Substances 0.000 abstract description 4
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 38
• 235000002639 sodium chloride Nutrition 0.000 description 27
• 229960001410 hydromorphone Drugs 0.000 description 25
• 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 description 25
• 239000003814 drug Substances 0.000 description 19
• 239000003112 inhibitor Substances 0.000 description 19
• 238000003786 synthesis reaction Methods 0.000 description 18
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
• LAZTZBKWNKFJLP-ZZNXZCQVSA-N O([C@@H]1[C@]23CCN([C@H](C4)[C@@H]3CCC1=O)C)C1=C2C4=CC=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O Chemical compound O([C@@H]1[C@]23CCN([C@H](C4)[C@@H]3CCC1=O)C)C1=C2C4=CC=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O LAZTZBKWNKFJLP-ZZNXZCQVSA-N 0.000 description 17
• 238000006243 chemical reaction Methods 0.000 description 16
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• 229960005181 morphine Drugs 0.000 description 12
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
• 101100244562 Pseudomonas aeruginosa (strain ATCC 15692 / DSM 22644 / CIP 104116 / JCM 14847 / LMG 12228 / 1C / PRS 101 / PAO1) oprD gene Proteins 0.000 description 11
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• 102000005962 receptors Human genes 0.000 description 11
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• 230000015572 biosynthetic process Effects 0.000 description 10
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• 241000282414 Homo sapiens Species 0.000 description 9
• CYAYKKUWALRRPA-RGDJUOJXSA-N [(2r,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-bromooxan-2-yl]methyl acetate Chemical compound CC(=O)OC[C@H]1O[C@H](Br)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O CYAYKKUWALRRPA-RGDJUOJXSA-N 0.000 description 9
• 229960004715 morphine sulfate Drugs 0.000 description 9
• GRVOTVYEFDAHCL-RTSZDRIGSA-N morphine sulfate pentahydrate Chemical compound O.O.O.O.O.OS(O)(=O)=O.O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O.O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O GRVOTVYEFDAHCL-RTSZDRIGSA-N 0.000 description 9
• 229940127240 opiate Drugs 0.000 description 9
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
• WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
• 230000000694 effects Effects 0.000 description 8
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• 241001465754 Metazoa Species 0.000 description 7
• 238000003556 assay Methods 0.000 description 7
• 230000005764 inhibitory process Effects 0.000 description 7
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• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 7
• 229910052757 nitrogen Inorganic materials 0.000 description 7
• 229940005483 opioid analgesics Drugs 0.000 description 7
• VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 6
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 6
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
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• 210000004027 cell Anatomy 0.000 description 6
• OROGSEYTTFOCAN-DNJOTXNNSA-N codeine Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC OROGSEYTTFOCAN-DNJOTXNNSA-N 0.000 description 6
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• DYUTXEVRMPFGTH-UHFFFAOYSA-N 4-(2,5-dimethylphenyl)-5-methyl-1,3-thiazol-2-amine Chemical compound S1C(N)=NC(C=2C(=CC=C(C)C=2)C)=C1C DYUTXEVRMPFGTH-UHFFFAOYSA-N 0.000 description 5
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
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• 230000000202 analgesic effect Effects 0.000 description 5
• 239000003795 chemical substances by application Substances 0.000 description 5
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• XYYVYLMBEZUESM-UHFFFAOYSA-N dihydrocodeine Natural products C1C(N(CCC234)C)C2C=CC(=O)C3OC2=C4C1=CC=C2OC XYYVYLMBEZUESM-UHFFFAOYSA-N 0.000 description 5
• OROGSEYTTFOCAN-UHFFFAOYSA-N hydrocodone Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OC OROGSEYTTFOCAN-UHFFFAOYSA-N 0.000 description 5
• 229960002738 hydromorphone hydrochloride Drugs 0.000 description 5
• 239000003446 ligand Substances 0.000 description 5
• UZHSEJADLWPNLE-GRGSLBFTSA-N naloxone Chemical compound O=C([C@@H]1O2)CC[C@@]3(O)[C@H]4CC5=CC=C(O)C2=C5[C@@]13CCN4CC=C UZHSEJADLWPNLE-GRGSLBFTSA-N 0.000 description 5
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