JP2004517882A - トリプトライドプロドラッグを使用する抗癌処置 - Google Patents
トリプトライドプロドラッグを使用する抗癌処置 Download PDFInfo
- Publication number
- JP2004517882A JP2004517882A JP2002557346A JP2002557346A JP2004517882A JP 2004517882 A JP2004517882 A JP 2004517882A JP 2002557346 A JP2002557346 A JP 2002557346A JP 2002557346 A JP2002557346 A JP 2002557346A JP 2004517882 A JP2004517882 A JP 2004517882A
- Authority
- JP
- Japan
- Prior art keywords
- group
- triptolide
- alkyl
- treatment
- lower alkyl
- 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.)
- Pending
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- DFBIRQPKNDILPW-CIVMWXNOSA-N Triptolide Chemical compound O=C1OCC([C@@H]2C3)=C1CC[C@]2(C)[C@]12O[C@H]1[C@@H]1O[C@]1(C(C)C)[C@@H](O)[C@]21[C@H]3O1 DFBIRQPKNDILPW-CIVMWXNOSA-N 0.000 title claims abstract description 47
- YKUJZZHGTWVWHA-UHFFFAOYSA-N triptolide Natural products COC12CC3OC3(C(C)C)C(O)C14OC4CC5C6=C(CCC25C)C(=O)OC6 YKUJZZHGTWVWHA-UHFFFAOYSA-N 0.000 title claims abstract description 36
- 229940002612 prodrug Drugs 0.000 title claims abstract description 23
- 239000000651 prodrug Substances 0.000 title claims abstract description 23
- 238000011394 anticancer treatment Methods 0.000 title claims abstract description 8
- 238000000034 method Methods 0.000 claims abstract description 31
- 238000011282 treatment Methods 0.000 claims abstract description 25
- 150000003839 salts Chemical class 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 28
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 18
- 229910052799 carbon Inorganic materials 0.000 claims description 15
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 14
- 208000029742 colonic neoplasm Diseases 0.000 claims description 13
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 239000001301 oxygen Substances 0.000 claims description 12
- 125000006413 ring segment Chemical group 0.000 claims description 12
- 206010009944 Colon cancer Diseases 0.000 claims description 11
- 150000007942 carboxylates Chemical class 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 239000011593 sulfur Substances 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 7
- 125000000623 heterocyclic group Chemical group 0.000 claims description 7
- 150000002485 inorganic esters Chemical class 0.000 claims description 7
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 6
- 208000026310 Breast neoplasm Diseases 0.000 claims description 6
- 206010060862 Prostate cancer Diseases 0.000 claims description 6
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 5
- 206010006187 Breast cancer Diseases 0.000 claims description 4
- WSNMPAVSZJSIMT-UHFFFAOYSA-N COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 Chemical compound COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 WSNMPAVSZJSIMT-UHFFFAOYSA-N 0.000 claims description 4
- 229930194542 Keto Natural products 0.000 claims description 4
- 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
- 229910019142 PO4 Inorganic materials 0.000 claims description 4
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 4
- 150000001299 aldehydes Chemical class 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- 150000001733 carboxylic acid esters Chemical class 0.000 claims description 4
- 150000001768 cations Chemical class 0.000 claims description 4
- 210000001072 colon Anatomy 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 150000002016 disaccharides Chemical group 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 4
- 125000000468 ketone group Chemical group 0.000 claims description 4
- 210000004072 lung Anatomy 0.000 claims description 4
- 150000002772 monosaccharides Chemical class 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 239000010452 phosphate Substances 0.000 claims description 4
- 229920000570 polyether Polymers 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- 125000003396 thiol group Chemical class [H]S* 0.000 claims description 4
- 150000004043 trisaccharides Chemical class 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 125000005228 aryl sulfonate group Chemical group 0.000 claims description 3
- 210000000481 breast Anatomy 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 3
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 2
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 2
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 claims description 2
- 150000008052 alkyl sulfonates Chemical class 0.000 claims description 2
- 229910052796 boron Inorganic materials 0.000 claims description 2
- UQSQSQZYBQSBJZ-UHFFFAOYSA-M fluorosulfonate Chemical compound [O-]S(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-M 0.000 claims description 2
- 201000005202 lung cancer Diseases 0.000 claims description 2
- 208000020816 lung neoplasm Diseases 0.000 claims description 2
- 229910021645 metal ion Inorganic materials 0.000 claims description 2
- 150000002823 nitrates Chemical class 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- 239000011574 phosphorus Substances 0.000 claims description 2
- 125000005208 trialkylammonium group Chemical group 0.000 claims description 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 claims 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 abstract description 34
- GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 abstract description 14
- 229960002949 fluorouracil Drugs 0.000 abstract description 14
- UWKQSNNFCGGAFS-XIFFEERXSA-N irinotecan Chemical compound C1=C2C(CC)=C3CN(C(C4=C([C@@](C(=O)OC4)(O)CC)C=4)=O)C=4C3=NC2=CC=C1OC(=O)N(CC1)CCC1N1CCCCC1 UWKQSNNFCGGAFS-XIFFEERXSA-N 0.000 abstract description 8
- 239000002246 antineoplastic agent Substances 0.000 abstract description 4
- 238000001727 in vivo Methods 0.000 abstract description 3
- 229960004768 irinotecan Drugs 0.000 abstract description 3
- 229940127089 cytotoxic agent Drugs 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 35
- 239000000203 mixture Substances 0.000 description 17
- HROMYAWHLUOUPY-AHCCQAQQSA-N omtriptolide Chemical compound O=C1OCC([C@@H]2C3)=C1CC[C@]2(C)[C@]12O[C@H]1[C@@H]1O[C@]1(C(C)C)[C@@H](OC(=O)CCC(O)=O)[C@]21[C@H]3O1 HROMYAWHLUOUPY-AHCCQAQQSA-N 0.000 description 12
- -1 and taxanes Chemical compound 0.000 description 10
- 210000004027 cell Anatomy 0.000 description 9
- 241000699670 Mus sp. Species 0.000 description 8
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 230000004614 tumor growth Effects 0.000 description 7
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- 201000011510 cancer Diseases 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 238000007920 subcutaneous administration Methods 0.000 description 5
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 5
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 125000000129 anionic group Chemical group 0.000 description 4
- 238000001990 intravenous administration Methods 0.000 description 4
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 4
- 239000000546 pharmaceutical excipient Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 239000003981 vehicle Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- 208000001333 Colorectal Neoplasms Diseases 0.000 description 3
- 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 3
- 239000004472 Lysine Substances 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000002252 acyl group Chemical group 0.000 description 3
- 239000000443 aerosol Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 230000034994 death Effects 0.000 description 3
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- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
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- LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 description 2
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- PUJWFVBVNFXCHZ-SQEQANQOSA-N Tripdiolide Chemical compound O=C1OCC([C@@H]2C3)=C1[C@@H](O)C[C@]2(C)[C@]12O[C@H]1[C@@H]1O[C@]1(C(C)C)[C@@H](O)[C@]21[C@H]3O1 PUJWFVBVNFXCHZ-SQEQANQOSA-N 0.000 description 2
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- 125000003710 aryl alkyl group Chemical group 0.000 description 2
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- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 150000004820 halides Chemical group 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
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- 230000001506 immunosuppresive effect Effects 0.000 description 2
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- 239000007927 intramuscular injection Substances 0.000 description 2
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- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
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- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/336—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having three-membered rings, e.g. oxirane, fumagillin
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- A—HUMAN NECESSITIES
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- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
- A61K31/343—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide condensed with a carbocyclic ring, e.g. coumaran, bufuralol, befunolol, clobenfurol, amiodarone
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
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- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Saccharide Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
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| US09/766,156 US6620843B2 (en) | 2001-01-19 | 2001-01-19 | Anticancer treatment using triptolide prodrugs |
| PCT/US2002/001650 WO2002056835A2 (en) | 2001-01-19 | 2002-01-18 | Anticancer treatment using triptolide prodrugs |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2004517882A true JP2004517882A (ja) | 2004-06-17 |
| JP2004517882A5 JP2004517882A5 (https=) | 2006-02-02 |
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| Application Number | Title | Priority Date | Filing Date |
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| JP2002557346A Pending JP2004517882A (ja) | 2001-01-19 | 2002-01-18 | トリプトライドプロドラッグを使用する抗癌処置 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US6620843B2 (https=) |
| EP (1) | EP1359909B1 (https=) |
| JP (1) | JP2004517882A (https=) |
| AT (1) | ATE406155T1 (https=) |
| AU (1) | AU2002237884B2 (https=) |
| CA (1) | CA2435322A1 (https=) |
| DE (1) | DE60228544D1 (https=) |
| WO (1) | WO2002056835A2 (https=) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006503831A (ja) * | 2002-09-18 | 2006-02-02 | 成都▲達▼▲遠▼▲薬▼物有限公司 | 高免疫抑制活性の水溶性トリプトリド誘導体及びその応用 |
| JP2012526148A (ja) * | 2009-05-07 | 2012-10-25 | リージェンツ オブ ザ ユニバーシティ オブ ミネソタ | トリプトリド製品 |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2468277A1 (en) | 2002-05-31 | 2012-06-27 | Pharmagenesis, Inc. | Triptolide derivatives for modulation of apoptosis and immunosuppression |
| WO2004058246A1 (en) * | 2002-12-17 | 2004-07-15 | Pharmagenesis, Inc. | Triptolide derivatives as immunomodulator and anticancer agents |
| US6943259B2 (en) * | 2003-02-25 | 2005-09-13 | Pharmagenesis, Inc. | Halogenated triptolide derivatives as immunomodulators and anticancer agents |
| WO2005062913A2 (en) * | 2003-12-24 | 2005-07-14 | Pharmagenesis, Inc. | Triplide 5,6-derivatives as immunomodulators and anticancer agents |
| EP1722806A4 (en) * | 2004-02-09 | 2009-09-16 | Pharmagenesis Inc | METHOD OF ISOLATING TRIPTOLIDE COMPOUNDS FROM TRIPTERYGIUM WILFORDII |
| WO2005084365A2 (en) * | 2004-03-02 | 2005-09-15 | Pharmagenesis, Inc. | Triptolide lactone ring derivatives as immunomodulators and anticancer agents |
| WO2006012204A2 (en) * | 2004-06-25 | 2006-02-02 | Pharmagenesis, Inc. | Method for treatment of inflammatory disorders using triptolide compounds |
| WO2006044496A2 (en) | 2004-10-13 | 2006-04-27 | Pharmagenesis, Inc. | Identification and screening of triptolide target molecules |
| EP1946758A1 (en) * | 2007-01-18 | 2008-07-23 | Pierre Fabre Medicament | Treatment of acute myeloid leukemia |
| US20100087337A1 (en) * | 2008-09-10 | 2010-04-08 | Bind Biosciences, Inc. | High Throughput Fabrication of Nanoparticles |
| CN104387406A (zh) | 2009-02-05 | 2015-03-04 | 药物起源公司 | 作为抗癌药和免疫调制剂的雷公藤内酯 c-环衍生物 |
| US9150600B2 (en) | 2009-05-07 | 2015-10-06 | Regents Of The University Of Minnesota | Triptolide prodrugs |
| US20130195896A1 (en) * | 2010-04-07 | 2013-08-01 | Steward Research And Specialty Projects Corporation | Compositions and methods for the treatment of a neoplasia |
| WO2013130603A1 (en) | 2012-02-27 | 2013-09-06 | Board Of Regents, The University Of Texas System | Ganglioside gd2 as a marker and target on cancer stem cells |
| AU2017214572A1 (en) * | 2016-02-04 | 2018-08-16 | The Johns Hopkins University | Glucose conjugates of triptolide, analogs and uses thereof |
| CN107698653B (zh) * | 2017-10-11 | 2019-08-27 | 中国农业科学院蜜蜂研究所 | 一种雷公藤甲素半抗原及其制备方法与应用 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4005108A (en) | 1973-04-03 | 1977-01-25 | Research Corporation | Novel anti-leukemic diterpenoid triepoxides |
| US5919816A (en) * | 1994-11-14 | 1999-07-06 | Bionumerik Pharmaceuticals, Inc. | Formulations and methods of reducing toxicity of antineoplastic agents |
| US5663335A (en) * | 1996-03-01 | 1997-09-02 | Pharmagenesis, Inc. | Immunosuppressive compounds and methods |
| US5962516A (en) | 1997-02-28 | 1999-10-05 | Pharmagenesis, Inc. | Immunosuppressive compounds and methods |
| CA2342901A1 (en) | 1998-09-02 | 2000-03-09 | Pharmagenesis, Inc. | Triptolide prodrugs having high aqueous solubility |
| US6548537B1 (en) * | 1998-09-02 | 2003-04-15 | Pharmagenesis, Inc. | Triptolide prodrugs having high aqueous solubility |
| US6294546B1 (en) * | 1999-08-30 | 2001-09-25 | The Broad Of Trustees Of The Leland Stanford Junior University | Uses of diterpenoid triepoxides as an anti-proliferative agent |
| EP1390358A4 (en) * | 2001-03-15 | 2004-06-16 | Pharmagenesis Inc | AMINO ACID DERIVATIVES OF TRIPTOLIDE COMPOUNDS AS IMMUNOMODULATORS AND ANTICROPHES |
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2001
- 2001-01-19 US US09/766,156 patent/US6620843B2/en not_active Expired - Fee Related
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2002
- 2002-01-18 EP EP02704187A patent/EP1359909B1/en not_active Expired - Lifetime
- 2002-01-18 CA CA002435322A patent/CA2435322A1/en not_active Abandoned
- 2002-01-18 JP JP2002557346A patent/JP2004517882A/ja active Pending
- 2002-01-18 WO PCT/US2002/001650 patent/WO2002056835A2/en not_active Ceased
- 2002-01-18 DE DE60228544T patent/DE60228544D1/de not_active Expired - Fee Related
- 2002-01-18 AT AT02704187T patent/ATE406155T1/de not_active IP Right Cessation
- 2002-01-18 AU AU2002237884A patent/AU2002237884B2/en not_active Ceased
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006503831A (ja) * | 2002-09-18 | 2006-02-02 | 成都▲達▼▲遠▼▲薬▼物有限公司 | 高免疫抑制活性の水溶性トリプトリド誘導体及びその応用 |
| JP2012526148A (ja) * | 2009-05-07 | 2012-10-25 | リージェンツ オブ ザ ユニバーシティ オブ ミネソタ | トリプトリド製品 |
Also Published As
| Publication number | Publication date |
|---|---|
| US6620843B2 (en) | 2003-09-16 |
| CA2435322A1 (en) | 2002-07-25 |
| DE60228544D1 (de) | 2008-10-09 |
| EP1359909A2 (en) | 2003-11-12 |
| US20020099051A1 (en) | 2002-07-25 |
| EP1359909A4 (en) | 2005-03-09 |
| WO2002056835A2 (en) | 2002-07-25 |
| AU2002237884B2 (en) | 2006-08-17 |
| EP1359909B1 (en) | 2008-08-27 |
| WO2002056835A3 (en) | 2003-02-27 |
| ATE406155T1 (de) | 2008-09-15 |
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