ES2216327T3 - Uso de iminoazucares alquilados para tratar la resistencia a multiples a farmacos. - Google Patents
Uso de iminoazucares alquilados para tratar la resistencia a multiples a farmacos.Info
- Publication number
- ES2216327T3 ES2216327T3 ES98956449T ES98956449T ES2216327T3 ES 2216327 T3 ES2216327 T3 ES 2216327T3 ES 98956449 T ES98956449 T ES 98956449T ES 98956449 T ES98956449 T ES 98956449T ES 2216327 T3 ES2216327 T3 ES 2216327T3
- Authority
- ES
- Spain
- Prior art keywords
- dideoxy
- imino
- galactitol
- glucitol
- tetrabutyrate
- Prior art date
- 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.)
- Expired - Lifetime
Links
- -1 galactitol compound Chemical class 0.000 claims abstract description 116
- 239000002246 antineoplastic agent Substances 0.000 claims abstract description 77
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 54
- 229940127089 cytotoxic agent Drugs 0.000 claims abstract description 53
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 49
- LXBIFEVIBLOUGU-UHFFFAOYSA-N Deoxymannojirimycin Natural products OCC1NCC(O)C(O)C1O LXBIFEVIBLOUGU-UHFFFAOYSA-N 0.000 claims abstract description 43
- LXBIFEVIBLOUGU-JGWLITMVSA-N duvoglustat Chemical compound OC[C@H]1NC[C@H](O)[C@@H](O)[C@@H]1O LXBIFEVIBLOUGU-JGWLITMVSA-N 0.000 claims abstract description 43
- 239000003814 drug Substances 0.000 claims abstract description 42
- 125000001424 substituent group Chemical group 0.000 claims abstract description 29
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 27
- 125000003118 aryl group Chemical group 0.000 claims abstract description 27
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 23
- 150000002367 halogens Chemical class 0.000 claims abstract description 23
- 238000011282 treatment Methods 0.000 claims abstract description 19
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 18
- 150000003839 salts Chemical class 0.000 claims abstract description 18
- 125000002252 acyl group Chemical group 0.000 claims abstract description 17
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 15
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 13
- 229910052698 phosphorus Inorganic materials 0.000 claims abstract description 13
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 13
- 125000004423 acyloxy group Chemical group 0.000 claims abstract description 12
- 125000003368 amide group Chemical group 0.000 claims abstract description 12
- 238000002360 preparation method Methods 0.000 claims abstract description 12
- 230000002265 prevention Effects 0.000 claims abstract description 11
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 10
- 230000036457 multidrug resistance Effects 0.000 claims abstract description 10
- 230000009467 reduction Effects 0.000 claims abstract description 10
- 125000003435 aroyl group Chemical group 0.000 claims abstract description 9
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 8
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
- 239000001257 hydrogen Substances 0.000 claims abstract description 7
- 125000001589 carboacyl group Chemical group 0.000 claims abstract description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract 3
- FBPFZTCFMRRESA-GUCUJZIJSA-N galactitol Chemical compound OC[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-GUCUJZIJSA-N 0.000 claims description 185
- 150000001875 compounds Chemical group 0.000 claims description 75
- 229960002920 sorbitol Drugs 0.000 claims description 57
- 229940079593 drug Drugs 0.000 claims description 38
- 206010048723 Multiple-drug resistance Diseases 0.000 claims description 37
- 239000008194 pharmaceutical composition Substances 0.000 claims description 24
- 239000003795 chemical substances by application Substances 0.000 claims description 21
- 230000000973 chemotherapeutic effect Effects 0.000 claims description 17
- 125000004429 atom Chemical group 0.000 claims description 14
- 230000000259 anti-tumor effect Effects 0.000 claims description 12
- 230000000694 effects Effects 0.000 claims description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 238000013270 controlled release Methods 0.000 claims description 9
- 210000002966 serum Anatomy 0.000 claims description 9
- RJURFGZVJUQBHK-UHFFFAOYSA-N actinomycin D Natural products CC1OC(=O)C(C(C)C)N(C)C(=O)CN(C)C(=O)C2CCCN2C(=O)C(C(C)C)NC(=O)C1NC(=O)C1=C(N)C(=O)C(C)=C2OC(C(C)=CC=C3C(=O)NC4C(=O)NC(C(N5CCCC5C(=O)N(C)CC(=O)N(C)C(C(C)C)C(=O)OC4C)=O)C(C)C)=C3N=C21 RJURFGZVJUQBHK-UHFFFAOYSA-N 0.000 claims description 8
- AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 claims description 6
- 229930013930 alkaloid Natural products 0.000 claims description 5
- 229940045799 anthracyclines and related substance Drugs 0.000 claims description 5
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 5
- KRNOSIJCJVCXKU-WRWGMCAJSA-N (2r,3r,4r,5s)-1-hexyl-2-(hydroxymethyl)piperidine-3,4,5-triol Chemical compound CCCCCCN1C[C@H](O)[C@@H](O)[C@H](O)[C@H]1CO KRNOSIJCJVCXKU-WRWGMCAJSA-N 0.000 claims description 4
- 229940124087 DNA topoisomerase II inhibitor Drugs 0.000 claims description 4
- 108010092160 Dactinomycin Proteins 0.000 claims description 4
- 239000000317 Topoisomerase II Inhibitor Substances 0.000 claims description 4
- 229940122803 Vinca alkaloid Drugs 0.000 claims description 4
- RJURFGZVJUQBHK-IIXSONLDSA-N actinomycin D Chemical group C[C@H]1OC(=O)[C@H](C(C)C)N(C)C(=O)CN(C)C(=O)[C@@H]2CCCN2C(=O)[C@@H](C(C)C)NC(=O)[C@H]1NC(=O)C1=C(N)C(=O)C(C)=C2OC(C(C)=CC=C3C(=O)N[C@@H]4C(=O)N[C@@H](C(N5CCC[C@H]5C(=O)N(C)CC(=O)N(C)[C@@H](C(C)C)C(=O)O[C@@H]4C)=O)C(C)C)=C3N=C21 RJURFGZVJUQBHK-IIXSONLDSA-N 0.000 claims description 4
- 150000003797 alkaloid derivatives Chemical class 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 229960000640 dactinomycin Drugs 0.000 claims description 4
- UQRORFVVSGFNRO-UTINFBMNSA-N miglustat Chemical compound CCCCN1C[C@H](O)[C@@H](O)[C@H](O)[C@H]1CO UQRORFVVSGFNRO-UTINFBMNSA-N 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- UQRORFVVSGFNRO-XFWSIPNHSA-N (2r,3s,4r,5s)-1-butyl-2-(hydroxymethyl)piperidine-3,4,5-triol Chemical compound CCCCN1C[C@H](O)[C@@H](O)[C@@H](O)[C@H]1CO UQRORFVVSGFNRO-XFWSIPNHSA-N 0.000 claims description 3
- 239000012623 DNA damaging agent Substances 0.000 claims description 3
- XDXDZDZNSLXDNA-TZNDIEGXSA-N Idarubicin Chemical compound C1[C@H](N)[C@H](O)[C@H](C)O[C@H]1O[C@@H]1C2=C(O)C(C(=O)C3=CC=CC=C3C3=O)=C3C(O)=C2C[C@@](O)(C(C)=O)C1 XDXDZDZNSLXDNA-TZNDIEGXSA-N 0.000 claims description 3
- 229960004679 doxorubicin Drugs 0.000 claims description 3
- 238000001802 infusion Methods 0.000 claims description 3
- 238000007911 parenteral administration Methods 0.000 claims description 3
- XDXDZDZNSLXDNA-UHFFFAOYSA-N Idarubicin Natural products C1C(N)C(O)C(C)OC1OC1C2=C(O)C(C(=O)C3=CC=CC=C3C3=O)=C3C(O)=C2CC(O)(C(C)=O)C1 XDXDZDZNSLXDNA-UHFFFAOYSA-N 0.000 claims description 2
- JXLYSJRDGCGARV-WWYNWVTFSA-N Vinblastine Natural products O=C(O[C@H]1[C@](O)(C(=O)OC)[C@@H]2N(C)c3c(cc(c(OC)c3)[C@]3(C(=O)OC)c4[nH]c5c(c4CCN4C[C@](O)(CC)C[C@H](C3)C4)cccc5)[C@@]32[C@H]2[C@@]1(CC)C=CCN2CC3)C JXLYSJRDGCGARV-WWYNWVTFSA-N 0.000 claims description 2
- 229940044684 anti-microtubule agent Drugs 0.000 claims description 2
- 230000006378 damage Effects 0.000 claims description 2
- VJJPUSNTGOMMGY-MRVIYFEKSA-N etoposide Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@H](C)OC[C@H]4O3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 VJJPUSNTGOMMGY-MRVIYFEKSA-N 0.000 claims description 2
- 229960005420 etoposide Drugs 0.000 claims description 2
- 229960000908 idarubicin Drugs 0.000 claims description 2
- 238000001990 intravenous administration Methods 0.000 claims description 2
- 229960003048 vinblastine Drugs 0.000 claims description 2
- JXLYSJRDGCGARV-XQKSVPLYSA-N vincaleukoblastine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-XQKSVPLYSA-N 0.000 claims description 2
- OLPXYCZRTKCCAE-XJFOESAGSA-N (2r,3r,4r,5s)-1-(2-cyclohexylethyl)-2-(hydroxymethyl)piperidine-3,4,5-triol Chemical compound OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)CN1CCC1CCCCC1 OLPXYCZRTKCCAE-XJFOESAGSA-N 0.000 claims 4
- FGHFGCSGYAOXKM-ZLMOABSSSA-N (2r,3r,4r,5s)-1-(2-ethylhexyl)-2-(hydroxymethyl)piperidine-3,4,5-triol Chemical compound CCCCC(CC)CN1C[C@H](O)[C@@H](O)[C@H](O)[C@H]1CO FGHFGCSGYAOXKM-ZLMOABSSSA-N 0.000 claims 4
- LDQVGLDWEACVHM-QKPAOTATSA-N (2r,3r,4r,5s)-1-(4-cyclohexylbutyl)-2-(hydroxymethyl)piperidine-3,4,5-triol Chemical compound OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)CN1CCCCC1CCCCC1 LDQVGLDWEACVHM-QKPAOTATSA-N 0.000 claims 4
- ZDMJHTAVXLUWDX-XJFOESAGSA-N (2r,3r,4r,5s)-1-(4-ethylhexyl)-2-(hydroxymethyl)piperidine-3,4,5-triol Chemical compound CCC(CC)CCCN1C[C@H](O)[C@@H](O)[C@H](O)[C@H]1CO ZDMJHTAVXLUWDX-XJFOESAGSA-N 0.000 claims 4
- KPUAQOGYSGTOCH-XMTFNYHQSA-N (2r,3r,4r,5s)-1-(6-cyclohexylhexyl)-2-(hydroxymethyl)piperidine-3,4,5-triol Chemical compound OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)CN1CCCCCCC1CCCCC1 KPUAQOGYSGTOCH-XMTFNYHQSA-N 0.000 claims 4
- ABSVMSSTYIUPSC-YVECIDJPSA-N (2r,3r,4r,5s)-1-(cyclohexylmethyl)-2-(hydroxymethyl)piperidine-3,4,5-triol Chemical compound OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)CN1CC1CCCCC1 ABSVMSSTYIUPSC-YVECIDJPSA-N 0.000 claims 4
- BTIIGIMBIARTEA-YVECIDJPSA-N (2r,3r,4r,5s)-1-benzyl-2-(hydroxymethyl)piperidine-3,4,5-triol Chemical compound OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)CN1CC1=CC=CC=C1 BTIIGIMBIARTEA-YVECIDJPSA-N 0.000 claims 4
- RGPAAJYPONXYEX-XMTFNYHQSA-N (2r,3r,4r,5s)-2-(hydroxymethyl)-1-(10-methylundecyl)piperidine-3,4,5-triol Chemical compound CC(C)CCCCCCCCCN1C[C@H](O)[C@@H](O)[C@H](O)[C@H]1CO RGPAAJYPONXYEX-XMTFNYHQSA-N 0.000 claims 4
- MUJKKNQFSSWNPA-LXTVHRRPSA-N (2r,3r,4r,5s)-2-(hydroxymethyl)-1-(3-phenylpropyl)piperidine-3,4,5-triol Chemical compound OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)CN1CCCC1=CC=CC=C1 MUJKKNQFSSWNPA-LXTVHRRPSA-N 0.000 claims 4
- KPYWEQMWPOEAKU-LXTVHRRPSA-N (2r,3r,4r,5s)-2-(hydroxymethyl)-1-(3-propylhexyl)piperidine-3,4,5-triol Chemical compound CCCC(CCC)CCN1C[C@H](O)[C@@H](O)[C@H](O)[C@H]1CO KPYWEQMWPOEAKU-LXTVHRRPSA-N 0.000 claims 4
- FXLFZDXCVQVPQQ-YVECIDJPSA-N (2r,3r,4r,5s)-2-(hydroxymethyl)-1-(5-methylhexyl)piperidine-3,4,5-triol Chemical compound CC(C)CCCCN1C[C@H](O)[C@@H](O)[C@H](O)[C@H]1CO FXLFZDXCVQVPQQ-YVECIDJPSA-N 0.000 claims 4
- QOOMCMUOTSHHOT-QKPAOTATSA-N (2r,3r,4r,5s)-2-(hydroxymethyl)-1-(8-methylnonyl)piperidine-3,4,5-triol Chemical compound CC(C)CCCCCCCN1C[C@H](O)[C@@H](O)[C@H](O)[C@H]1CO QOOMCMUOTSHHOT-QKPAOTATSA-N 0.000 claims 4
- ADXDQKAZSUDZBL-YYIAUSFCSA-N (2r,3r,4r,5s)-2-(hydroxymethyl)-1-(9-methyldecyl)piperidine-3,4,5-triol Chemical compound CC(C)CCCCCCCCN1C[C@H](O)[C@@H](O)[C@H](O)[C@H]1CO ADXDQKAZSUDZBL-YYIAUSFCSA-N 0.000 claims 4
- HKOKFWKDTXFLHY-ZLMOABSSSA-N (2r,3r,4r,5s)-2-(hydroxymethyl)-1-octan-4-ylpiperidine-3,4,5-triol Chemical compound CCCCC(CCC)N1C[C@H](O)[C@@H](O)[C@H](O)[C@H]1CO HKOKFWKDTXFLHY-ZLMOABSSSA-N 0.000 claims 4
- POSGIPKNBOVVGB-XMTFNYHQSA-N (2r,3r,4r,5s)-2-(hydroxymethyl)-1-(6-phenylhexyl)piperidine-3,4,5-triol Chemical compound OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)CN1CCCCCCC1=CC=CC=C1 POSGIPKNBOVVGB-XMTFNYHQSA-N 0.000 claims 3
- DXCCOXQKDKQOMJ-LMTUPJBHSA-N (2R,3R,4R,5S)-1-(7-butyldodecan-6-yl)-2-(hydroxymethyl)piperidine-3,4,5-triol Chemical compound C(CCCC)C(CCCC)C(CCCCC)N1C[C@H](O)[C@@H](O)[C@H](O)[C@H]1CO DXCCOXQKDKQOMJ-LMTUPJBHSA-N 0.000 claims 2
- MBQCNYZEYQQTEE-YVECIDJPSA-N (2r,3r,4r,5s)-1-heptyl-2-(hydroxymethyl)piperidine-3,4,5-triol Chemical compound CCCCCCCN1C[C@H](O)[C@@H](O)[C@H](O)[C@H]1CO MBQCNYZEYQQTEE-YVECIDJPSA-N 0.000 claims 2
- VGSQNAQYXKTCLP-XJFOESAGSA-N (2r,3r,4r,5s)-2-(hydroxymethyl)-1-octylpiperidine-3,4,5-triol Chemical compound CCCCCCCCN1C[C@H](O)[C@@H](O)[C@H](O)[C@H]1CO VGSQNAQYXKTCLP-XJFOESAGSA-N 0.000 claims 2
- DUKKBXHYYSHSAI-BZNPZCIMSA-N (2r,3r,4r,5s)-2-(hydroxymethyl)-1-propylpiperidine-3,4,5-triol Chemical compound CCCN1C[C@H](O)[C@@H](O)[C@H](O)[C@H]1CO DUKKBXHYYSHSAI-BZNPZCIMSA-N 0.000 claims 2
- YJGVMLPVUAXIQN-LGWHJFRWSA-N (5s,5ar,8ar,9r)-5-hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5h-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one Chemical compound COC1=C(OC)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O)[C@@H]3[C@@H]2C(OC3)=O)=C1 YJGVMLPVUAXIQN-LGWHJFRWSA-N 0.000 claims 2
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- NRUKOCRGYNPUPR-QBPJDGROSA-N teniposide Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@@H](OC[C@H]4O3)C=3SC=CC=3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 NRUKOCRGYNPUPR-QBPJDGROSA-N 0.000 claims 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/475—Quinolines; Isoquinolines having an indole ring, e.g. yohimbine, reserpine, strychnine, vinblastine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Organic Chemistry (AREA)
- Epidemiology (AREA)
- Molecular Biology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US6505197P | 1997-11-10 | 1997-11-10 | |
| US65051P | 1997-11-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2216327T3 true ES2216327T3 (es) | 2004-10-16 |
Family
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| ES98956449T Expired - Lifetime ES2216327T3 (es) | 1997-11-10 | 1998-11-09 | Uso de iminoazucares alquilados para tratar la resistencia a multiples a farmacos. |
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| EP (1) | EP1030839B1 (enExample) |
| JP (1) | JP2001522833A (enExample) |
| AR (1) | AR018732A1 (enExample) |
| AT (1) | ATE258919T1 (enExample) |
| AU (1) | AU753336B2 (enExample) |
| CA (1) | CA2309321A1 (enExample) |
| DE (1) | DE69821520T2 (enExample) |
| DK (1) | DK1030839T3 (enExample) |
| ES (1) | ES2216327T3 (enExample) |
| MY (1) | MY122499A (enExample) |
| PT (1) | PT1030839E (enExample) |
| TW (1) | TW581677B (enExample) |
| WO (1) | WO1999024401A1 (enExample) |
| ZA (1) | ZA9810210B (enExample) |
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| BR9813508A (pt) | 1997-12-11 | 2000-10-03 | Univ Oxford | Inibição de replicação viral associada com membrana |
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| WO2000056334A1 (en) * | 1999-03-19 | 2000-09-28 | The Trustees Of Boston College | Use of imino sugars for anti-tumor therapy |
| GB0100889D0 (en) | 2001-01-12 | 2001-02-21 | Oxford Glycosciences Uk Ltd | Compounds |
| US7256005B2 (en) | 1999-08-10 | 2007-08-14 | The Chancellor, Masters And Scholars Of The University Of Oxford | Methods for identifying iminosugar derivatives that inhibit HCV p7 ion channel activity |
| JP2003506406A (ja) * | 1999-08-10 | 2003-02-18 | ザ・チャンセラー・マスターズ・アンド・スカラーズ・オブ・ザ・ユニバーシティ・オブ・オックスフォード | 長鎖ｎ−アルキル化合物およびそのオキサ誘導体 |
| GB0006539D0 (en) * | 2000-03-17 | 2000-05-10 | Oxford Glycosciences Uk Ltd | Therapies |
| US6693099B2 (en) | 2000-10-17 | 2004-02-17 | The Procter & Gamble Company | Substituted piperazine compounds optionally containing a quinolyl moiety for treating multidrug resistance |
| US6376514B1 (en) | 2000-10-17 | 2002-04-23 | The Procter & Gamble Co. | Substituted six-membered heterocyclic compounds useful for treating multidrug resistance and compositions and methods thereof |
| CA2465886A1 (en) * | 2001-11-07 | 2003-05-15 | Kathleen S. Crowley | Methods of promoting uptake and nuclear accumulation of polyamides in eukaryotic cells |
| ITMI20021040A1 (it) * | 2002-05-16 | 2003-11-17 | Novuspharma Spa | Composizioni farmaceutiche iniettabili di un derivato antracenedionico ad attivita' antitumorale |
| US6982253B2 (en) * | 2002-06-05 | 2006-01-03 | Supergen, Inc. | Liquid formulation of decitabine and use of the same |
| CA2492404C (en) | 2002-07-17 | 2012-02-07 | Oxford Glycosciences (Uk) Ltd | Piperidinetriol derivatives as inhibitors of glycosylceramide synthase |
| CA2492410C (en) | 2002-07-17 | 2011-09-13 | Oxford Glycosciences (Uk) Ltd | Piperidinetriol derivatives as inhibitors of glycosylceramidsynthase |
| US8034831B2 (en) * | 2002-11-06 | 2011-10-11 | Celgene Corporation | Methods for the treatment and management of myeloproliferative diseases using 4-(amino)-2-(2,6-Dioxo(3-piperidyl)-isoindoline-1,3-dione in combination with other therapies |
| US7563810B2 (en) * | 2002-11-06 | 2009-07-21 | Celgene Corporation | Methods of using 3-(4-amino-1-oxo-1,3-dihydroisoindol-2-yl)-piperidine-2,6-dione for the treatment and management of myeloproliferative diseases |
| US7785621B2 (en) * | 2003-01-31 | 2010-08-31 | Childrens Hospital Los Angeles | Oral compositions of fenretinide having increased bioavailability and methods of using the same |
| EP1597231A1 (en) * | 2003-02-20 | 2005-11-23 | Ranbaxy Laboratories, Ltd. | Derivatives of azasugars as anticancer agents |
| GB0313677D0 (en) | 2003-06-13 | 2003-07-16 | Oxford Glycosciences Uk Ltd | Novel compound |
| GB0313678D0 (en) | 2003-06-13 | 2003-07-16 | Oxford Glycosciences Uk Ltd | Novel compounds |
| GB0400812D0 (en) * | 2004-01-14 | 2004-02-18 | Celltech R&D Ltd | Novel compounds |
| GB0403165D0 (en) * | 2004-02-12 | 2004-03-17 | Ct | Novel uses for proton pump inhibitors |
| WO2005123055A2 (en) * | 2004-06-14 | 2005-12-29 | Musc Foundation For Research Development | Methods for treating inflammatory disorders |
| EP3441090A1 (en) | 2005-05-17 | 2019-02-13 | Amicus Therapeutics, Inc. | A method for the treatment of pompe disease using 1-deoxynojirimycin and derivatives |
| DOP2006000277A (es) | 2005-12-12 | 2007-08-31 | Bayer Pharmaceuticals Corp | Anticuerpos anti mn y métodos para su utilización |
| WO2007140184A2 (en) | 2006-05-24 | 2007-12-06 | United Therapeutics Corporation | Deoxynojirimycin and d-arabinitol analogs and methods of using |
| WO2008088581A2 (en) | 2006-08-02 | 2008-07-24 | United Therapeutics Corporation | Liposome treatment of viral infections |
| US8097728B2 (en) * | 2007-04-30 | 2012-01-17 | Philadelphia Health & Education Corporation | Iminosugar compounds with antiflavirus activity |
| US20090252785A1 (en) * | 2008-03-26 | 2009-10-08 | University Of Oxford | Endoplasmic reticulum targeting liposomes |
| US8703744B2 (en) | 2009-03-27 | 2014-04-22 | The Chancellor, Masters And Scholars Of The University Of Oxford | Cholesterol level lowering liposomes |
| AR076284A1 (es) | 2009-04-29 | 2011-06-01 | Bayer Schering Pharma Ag | Inmunoconjugados de antimesotelina y usos de los mismos |
| KR20230066482A (ko) | 2012-03-07 | 2023-05-15 | 아미쿠스 세라퓨틱스, 인코포레이티드 | 폼페병의 치료를 위한 고농도 알파-글루코시다제 조성물 |
| EP2968300A4 (en) | 2013-03-15 | 2016-09-28 | Unither Virology Llc | ANTIBACTERIAL COMPOUNDS |
| MY186336A (en) | 2014-09-30 | 2021-07-13 | Amicus Therapeutics Inc | Highly potent acid alpha-glucosidase with enhanced carbohydrates |
| CA3010205A1 (en) | 2015-12-30 | 2017-07-06 | Amicus Therapeutics, Inc. | Augmented acid alpha-glucosidase for the treatment of pompe disease |
| IL301319A (en) | 2016-03-30 | 2023-05-01 | Amicus Therapeutics Inc | Formulations that include recombinant acid alpha-glucosidase |
| MX2018011951A (es) | 2016-03-30 | 2019-02-13 | Amicus Therapeutics Inc | Metodo para seleccionar proteinas recombinantes ricas en m6p. |
| EP3624831B1 (en) | 2017-05-15 | 2023-03-29 | Amicus Therapeutics, Inc. | Recombinant human acid alpha-glucosidase |
| CR20220601A (es) * | 2020-05-07 | 2023-04-11 | Alectos Therapeutics Inc | Inhibidores de glucosilceramidasa no lisosomal y los usos de los mismos |
| WO2025017212A1 (en) * | 2023-07-20 | 2025-01-23 | Katholieke Universiteit Leuven | Udp-glucose ceramide glucosyltransferase synthase (ugcg) inhibitors in the treatment of cancer |
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| US452406A (en) | 1891-05-19 | Hanger for pictures | ||
| YU33730B (en) | 1967-04-18 | 1978-02-28 | Farmaceutici Italia | Process for preparing a novel antibiotic substance and salts thereof |
| GB1555654A (en) | 1977-06-25 | 1979-11-14 | Exxon Research Engineering Co | Agricultural burner apparatus |
| US4065562A (en) | 1975-12-29 | 1977-12-27 | Nippon Shinyaku Co., Ltd. | Method and composition for reducing blood glucose levels |
| US4012448A (en) | 1976-01-15 | 1977-03-15 | Stanford Research Institute | Synthesis of adriamycin and 7,9-epiadriamycin |
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| GB2020278B (en) | 1978-05-03 | 1983-02-23 | Nippon Shinyaku Co Ltd | Moranoline dervitives |
| US4327725A (en) | 1980-11-25 | 1982-05-04 | Alza Corporation | Osmotic device with hydrogel driving member |
| DE3049446A1 (de) | 1980-12-30 | 1982-07-29 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von 1,5-didesoxy-1,5-imino-d-glucitol und dessen n-derivaten |
| US4765989A (en) | 1983-05-11 | 1988-08-23 | Alza Corporation | Osmotic device for administering certain drugs |
| US4612008A (en) | 1983-05-11 | 1986-09-16 | Alza Corporation | Osmotic device with dual thermodynamic activity |
| US4783337A (en) | 1983-05-11 | 1988-11-08 | Alza Corporation | Osmotic system comprising plurality of members for dispensing drug |
| WO1987003903A1 (en) | 1985-12-23 | 1987-07-02 | Fred Hutchinson Cancer Research Center | Regulating retroviral replication, infection, and pathogenesis |
| GB2186485B (en) | 1986-02-13 | 1988-09-07 | Ethical Pharma Ltd | Slow release formulation |
| DE3611841A1 (de) | 1986-04-09 | 1987-10-15 | Bayer Ag | Verfahren zur herstellung von 1-desoxynojirimycin und dessen n-derivaten |
| US4849430A (en) * | 1988-03-09 | 1989-07-18 | Monsanto Company | Method of inhibiting virus |
| ES2108680T3 (es) * | 1987-12-21 | 1998-01-01 | Monsanto Co | Uso del derivado n-n-butilo de desoxinojirimicina en la fabricacion de un medicamento. |
| FI101344B1 (fi) | 1988-03-31 | 1998-06-15 | Tanabe Seiyaku Co | Menetelmä valmistaa valmiste, josta kontrolloidusti vapautuu farmaseuttisesti aktiivista ainetta |
| US5041441A (en) | 1988-04-04 | 1991-08-20 | The Regents Of The University Of Michigan | Method of chemotherapy using 1-phenyl-2-decanoylamino-3-morpholino-1-propanol |
| EP0350012A3 (en) | 1988-07-08 | 1990-09-05 | Meiji Seika Kaisha Ltd. | Antiviral composition |
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| US5310745A (en) | 1988-11-03 | 1994-05-10 | G. D. Searle & Co. | Antiviral compounds |
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| US5030638A (en) | 1990-02-26 | 1991-07-09 | G. D. Searle & Co. | Method of antiviral enhancement |
| DE4009561A1 (de) | 1990-03-24 | 1991-09-26 | Bayer Ag | Neue desoxynojirimycinderivate, verfahren zu ihrer herstellung und ihre verwendung in arzneimitteln |
| US5536732A (en) * | 1990-04-27 | 1996-07-16 | Merrell Pharmaceuticals Inc. | N-derivatives of 1-deoxy nojirimycin |
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| DK0477160T3 (da) | 1990-09-20 | 1996-05-20 | Monsanto Co | Fremgangsmåde til fremstilling af N-substitueret 1-deoxynojirimycin |
| US5190765A (en) | 1991-06-27 | 1993-03-02 | Alza Corporation | Therapy delayed |
| ZA931934B (en) | 1992-03-18 | 1993-03-18 | Us Bioscience | Compostitions of N-(phosphonoacetyl)-L-aspartic acid and methods of their use as broad spectrum antivirals |
| IL105090A (en) | 1992-03-18 | 1998-08-16 | Us Bioscience | Acid N) phosphonoacetyl (Aspartic L in a broad spectrum antiviral agent |
| US5331096A (en) | 1992-04-01 | 1994-07-19 | G. D. Searle & Co. | 2- and 3-sulfur derivatives of 1,5-iminosugars |
| US5258518A (en) * | 1992-04-01 | 1993-11-02 | G. D. Searle & Co. | 2-substituted tertiary carbinol derivatives of deoxynojirimycin |
| EP0655457A1 (en) | 1992-08-14 | 1995-05-31 | Nippon Shinyaku Company, Limited | Moranoline derivative |
| US5399567A (en) | 1993-05-13 | 1995-03-21 | Monsanto Company | Method of treating cholera |
| WO1995006061A1 (en) | 1993-08-20 | 1995-03-02 | G.D. Searle & Co. | Retroviral protease inhibitors and combinations thereof |
| EP0739205B1 (en) | 1994-01-13 | 1999-11-24 | G.D. Searle & Co. | Use of n-alkyl derivatives of 1,5-dideoxy-1,5-imino-d-glucitol for the treatment of hepatitis b virus infections |
| WO1995022975A1 (en) * | 1994-02-25 | 1995-08-31 | G.D. Searle & Co. | Use of 1-deoxynojirimycin and its derivatives for treating mammals infected with respiratory syncytial virus |
| US5451679A (en) | 1994-03-08 | 1995-09-19 | G. D. Searle & Co. | 2-chloro and 2-bromo derivatives of 1,5-iminosugars |
| US5763470A (en) | 1995-06-07 | 1998-06-09 | Sugen Inc. | Benzopyran compounds and methods for their use |
| WO1997000881A1 (fr) | 1995-06-22 | 1997-01-09 | Nippon Shinyaku Co., Ltd. | Derives de la moranoline |
| EP1007058B1 (en) | 1997-02-14 | 2005-05-18 | G.D. Searle LLC. | Use of (n)-substituted-1,5-dideoxy-1,5-imino-d-glucitol compounds in combination therapy for treating hepatitis virus infections |
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1998
- 1998-11-09 MY MYPI98005087A patent/MY122499A/en unknown
- 1998-11-09 DK DK98956449T patent/DK1030839T3/da active
- 1998-11-09 ZA ZA9810210A patent/ZA9810210B/xx unknown
- 1998-11-09 CA CA002309321A patent/CA2309321A1/en not_active Abandoned
- 1998-11-09 PT PT98956449T patent/PT1030839E/pt unknown
- 1998-11-09 EP EP98956449A patent/EP1030839B1/en not_active Expired - Lifetime
- 1998-11-09 DE DE69821520T patent/DE69821520T2/de not_active Expired - Fee Related
- 1998-11-09 AU AU12973/99A patent/AU753336B2/en not_active Ceased
- 1998-11-09 WO PCT/US1998/023239 patent/WO1999024401A1/en not_active Ceased
- 1998-11-09 JP JP2000520415A patent/JP2001522833A/ja not_active Withdrawn
- 1998-11-09 AT AT98956449T patent/ATE258919T1/de not_active IP Right Cessation
- 1998-11-09 ES ES98956449T patent/ES2216327T3/es not_active Expired - Lifetime
- 1998-11-10 US US09/189,177 patent/US6225325B1/en not_active Expired - Fee Related
- 1998-11-10 AR ARP980105672A patent/AR018732A1/es unknown
- 1998-12-11 TW TW087118629A patent/TW581677B/zh not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| WO1999024401A1 (en) | 1999-05-20 |
| MY122499A (en) | 2006-04-29 |
| AU753336B2 (en) | 2002-10-17 |
| ZA9810210B (en) | 1999-07-14 |
| AU1297399A (en) | 1999-05-31 |
| DE69821520D1 (de) | 2004-03-11 |
| PT1030839E (pt) | 2004-05-31 |
| DE69821520T2 (de) | 2004-12-16 |
| US6225325B1 (en) | 2001-05-01 |
| AR018732A1 (es) | 2001-12-12 |
| TW581677B (en) | 2004-04-01 |
| CA2309321A1 (en) | 1999-05-20 |
| DK1030839T3 (da) | 2004-05-03 |
| EP1030839A1 (en) | 2000-08-30 |
| ATE258919T1 (de) | 2004-02-15 |
| JP2001522833A (ja) | 2001-11-20 |
| EP1030839B1 (en) | 2004-02-04 |
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