JPS59108786A - ブリオスタチン類 - Google Patents
ブリオスタチン類Info
- Publication number
- JPS59108786A JPS59108786A JP58215148A JP21514883A JPS59108786A JP S59108786 A JPS59108786 A JP S59108786A JP 58215148 A JP58215148 A JP 58215148A JP 21514883 A JP21514883 A JP 21514883A JP S59108786 A JPS59108786 A JP S59108786A
- Authority
- JP
- Japan
- Prior art keywords
- bryostatin
- acid
- methanol
- spectrum
- compound
- 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.)
- Granted
Links
- 229960005520 bryostatin Drugs 0.000 title description 44
- MJQUEDHRCUIRLF-YCVQJEHTSA-N bryostatins Chemical compound C([C@@H]1CC(/[C@@H]([C@@](C(C)(C)/C=C/2)(O)O1)OC(=O)/C=C/C=C/CCC)=C\C(=O)OC)C([C@@H](C)O)OC(=O)C[C@H](O)C[C@@H](O1)C[C@H](OC(C)=O)C(C)(C)[C@]1(O)C[C@@H]1C\C(=C\C(=O)OC)C[C@H]\2O1 MJQUEDHRCUIRLF-YCVQJEHTSA-N 0.000 title description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 77
- MJQUEDHRCUIRLF-TVIXENOKSA-N bryostatin 1 Chemical compound C([C@@H]1CC(/[C@@H]([C@@](C(C)(C)/C=C/2)(O)O1)OC(=O)/C=C/C=C/CCC)=C\C(=O)OC)[C@H]([C@@H](C)O)OC(=O)C[C@H](O)C[C@@H](O1)C[C@H](OC(C)=O)C(C)(C)[C@]1(O)C[C@@H]1C\C(=C\C(=O)OC)C[C@H]\2O1 MJQUEDHRCUIRLF-TVIXENOKSA-N 0.000 claims description 66
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 57
- 229960005539 bryostatin 1 Drugs 0.000 claims description 31
- BSNHYLUEHJOXFN-HBUIWOJHSA-N 87370-86-3 Chemical compound C([C@@H]1[C@H]2OC(=O)C=C2[C@@H]([C@@](C(C)(C)/C=C/2)(O)O1)OC(=O)/C=C/C=C/CCC)[C@H]([C@@H](C)O)OC(=O)C[C@H](O)C[C@@H](O1)C[C@H](OC(C)=O)C(C)(C)[C@]1(O)C[C@@H]1C\C(=C\C(=O)OC)C[C@H]\2O1 BSNHYLUEHJOXFN-HBUIWOJHSA-N 0.000 claims description 20
- LIPGUSBNMQRYNL-IZBIBDMISA-N bryostatin 2 Chemical compound C([C@@H]1CC(/[C@@H]([C@@](C(C)(C)/C=C/2)(O)O1)OC(=O)/C=C/C=C/CCC)=C\C(=O)OC)[C@H]([C@@H](C)O)OC(=O)C[C@H](O)C[C@@H](O1)C[C@H](O)C(C)(C)[C@]1(O)C[C@@H]1C\C(=C\C(=O)OC)C[C@H]\2O1 LIPGUSBNMQRYNL-IZBIBDMISA-N 0.000 claims description 19
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 16
- 201000010099 disease Diseases 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 15
- 238000004809 thin layer chromatography Methods 0.000 claims description 11
- 206010028980 Neoplasm Diseases 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 10
- 238000002844 melting Methods 0.000 claims description 8
- 230000008018 melting Effects 0.000 claims description 8
- 239000007787 solid Substances 0.000 claims description 7
- 230000003287 optical effect Effects 0.000 claims description 6
- 238000002329 infrared spectrum Methods 0.000 claims description 4
- 238000002211 ultraviolet spectrum Methods 0.000 claims description 4
- 238000000862 absorption spectrum Methods 0.000 claims 4
- 206010061217 Infestation Diseases 0.000 claims 1
- 235000010575 Pueraria lobata Nutrition 0.000 claims 1
- 241000219781 Pueraria montana var. lobata Species 0.000 claims 1
- 208000035269 cancer or benign tumor Diseases 0.000 claims 1
- 101150084411 crn1 gene Proteins 0.000 claims 1
- 238000002143 fast-atom bombardment mass spectrum Methods 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 37
- MUIWQCKLQMOUAT-AKUNNTHJSA-N bryostatin 20 Natural products COC(=O)C=C1C[C@@]2(C)C[C@]3(O)O[C@](C)(C[C@@H](O)CC(=O)O[C@](C)(C[C@@]4(C)O[C@](O)(CC5=CC(=O)O[C@]45C)C(C)(C)C=C[C@@](C)(C1)O2)[C@@H](C)O)C[C@H](OC(=O)C(C)(C)C)C3(C)C MUIWQCKLQMOUAT-AKUNNTHJSA-N 0.000 description 36
- 239000004480 active ingredient Substances 0.000 description 20
- 239000002775 capsule Substances 0.000 description 20
- -1 unsaturated alicyclic carboxylic acid Chemical class 0.000 description 18
- 241001465754 Metazoa Species 0.000 description 15
- 239000000843 powder Substances 0.000 description 15
- 239000003826 tablet Substances 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 238000011282 treatment Methods 0.000 description 14
- 239000000463 material Substances 0.000 description 13
- 238000000034 method Methods 0.000 description 13
- 230000001613 neoplastic effect Effects 0.000 description 13
- 239000000725 suspension Substances 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- 239000002253 acid Substances 0.000 description 10
- 239000013078 crystal Substances 0.000 description 10
- 239000007788 liquid Substances 0.000 description 10
- 238000001228 spectrum Methods 0.000 description 10
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
- 239000004615 ingredient Substances 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 8
- 239000002552 dosage form Substances 0.000 description 8
- 239000000546 pharmaceutical excipient Substances 0.000 description 8
- WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 7
- 239000000284 extract Substances 0.000 description 7
- 238000000605 extraction Methods 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 6
- 239000012530 fluid Substances 0.000 description 6
- 238000002347 injection Methods 0.000 description 6
- 239000007924 injection Substances 0.000 description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
- 241000700670 Bryozoa Species 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000011049 filling Methods 0.000 description 5
- 238000001819 mass spectrum Methods 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- 241000700675 Bugula neritina Species 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 4
- 230000000975 bioactive effect Effects 0.000 description 4
- JBDSSBMEKXHSJF-UHFFFAOYSA-N cyclopentanecarboxylic acid Chemical compound OC(=O)C1CCCC1 JBDSSBMEKXHSJF-UHFFFAOYSA-N 0.000 description 4
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000000829 suppository 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
- 241000416162 Astragalus gummifer Species 0.000 description 3
- 239000005711 Benzoic acid Substances 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229920001615 Tragacanth Polymers 0.000 description 3
- 239000011149 active material Substances 0.000 description 3
- 125000002252 acyl group Chemical group 0.000 description 3
- 239000000443 aerosol Substances 0.000 description 3
- 230000000118 anti-neoplastic effect Effects 0.000 description 3
- 230000000259 anti-tumor effect Effects 0.000 description 3
- 239000007900 aqueous suspension Substances 0.000 description 3
- 235000010233 benzoic acid Nutrition 0.000 description 3
- 238000013375 chromatographic separation Methods 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 238000005564 crystal structure determination Methods 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000012634 fragment Substances 0.000 description 3
- 241000411851 herbal medicine Species 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 238000001802 infusion Methods 0.000 description 3
- 235000019359 magnesium stearate Nutrition 0.000 description 3
- 229920000609 methyl cellulose Polymers 0.000 description 3
- 239000001923 methylcellulose Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 230000005855 radiation Effects 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000002893 slag Substances 0.000 description 3
- 238000000638 solvent extraction Methods 0.000 description 3
- 239000006188 syrup Substances 0.000 description 3
- 235000020357 syrup Nutrition 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 235000012222 talc Nutrition 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- UIAFKZKHHVMJGS-UHFFFAOYSA-N 2,4-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1O UIAFKZKHHVMJGS-UHFFFAOYSA-N 0.000 description 2
- XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 2
- ZEYHEAKUIGZSGI-UHFFFAOYSA-N 4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1 ZEYHEAKUIGZSGI-UHFFFAOYSA-N 0.000 description 2
- 244000215068 Acacia senegal Species 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 229920002261 Corn starch Polymers 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- 229920000084 Gum arabic Polymers 0.000 description 2
- 241000282412 Homo Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 241000055277 Neritina Species 0.000 description 2
- 239000004264 Petrolatum Substances 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000000205 acacia gum Substances 0.000 description 2
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- 230000021736 acetylation Effects 0.000 description 2
- 238000006640 acetylation reaction Methods 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 239000003242 anti bacterial agent Substances 0.000 description 2
- 229940088710 antibiotic agent Drugs 0.000 description 2
- 239000008135 aqueous vehicle Substances 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 210000003123 bronchiole Anatomy 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000008120 corn starch Substances 0.000 description 2
- LJOODBDWMQKMFB-UHFFFAOYSA-N cyclohexylacetic acid Chemical compound OC(=O)CC1CCCCC1 LJOODBDWMQKMFB-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 230000008034 disappearance Effects 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
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- 235000003599 food sweetener Nutrition 0.000 description 2
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 description 2
- 239000007903 gelatin capsule Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 230000036541 health Effects 0.000 description 2
- KEMQGTRYUADPNZ-UHFFFAOYSA-N heptadecanoic acid Chemical compound CCCCCCCCCCCCCCCCC(O)=O KEMQGTRYUADPNZ-UHFFFAOYSA-N 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- IGMNYECMUMZDDF-UHFFFAOYSA-N homogentisic acid Chemical compound OC(=O)CC1=CC(O)=CC=C1O IGMNYECMUMZDDF-UHFFFAOYSA-N 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000007912 intraperitoneal administration Methods 0.000 description 2
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 150000002596 lactones Chemical class 0.000 description 2
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- 150000002678 macrocyclic compounds Chemical class 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 2
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 2
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- 239000012452 mother liquor Substances 0.000 description 2
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
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- 210000003800 pharynx Anatomy 0.000 description 2
- 238000005191 phase separation Methods 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
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- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 2
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- SZHOJFHSIKHZHA-UHFFFAOYSA-N tridecanoic acid Chemical compound CCCCCCCCCCCCC(O)=O SZHOJFHSIKHZHA-UHFFFAOYSA-N 0.000 description 2
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- KAZDQJDOHTVZDQ-VDQHJUMDSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2,5-diaminopentanoic acid Chemical compound NCCC[C@H](N)C(O)=O.NCCCC[C@H](N)C(O)=O KAZDQJDOHTVZDQ-VDQHJUMDSA-N 0.000 description 1
- WZPJZJQDNCHIOT-YTLIFORHSA-N (2s)-2-amino-3-hydroxypropanoic acid;(2s)-2-amino-3-phenylpropanoic acid;(2s)-pyrrolidine-2-carboxylic acid Chemical compound OC[C@H](N)C(O)=O.OC(=O)[C@@H]1CCCN1.OC(=O)[C@@H](N)CC1=CC=CC=C1 WZPJZJQDNCHIOT-YTLIFORHSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- KJTLQQUUPVSXIM-ZCFIWIBFSA-N (R)-mevalonic acid Chemical compound OCC[C@](O)(C)CC(O)=O KJTLQQUUPVSXIM-ZCFIWIBFSA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 description 1
- HVPLGNPSEHQUFK-UHFFFAOYSA-N 1-bromo-3,5-dimethylcyclohexane-1-carboxylic acid Chemical compound CC1CC(C)CC(Br)(C(O)=O)C1 HVPLGNPSEHQUFK-UHFFFAOYSA-N 0.000 description 1
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 1
- PRPINYUDVPFIRX-UHFFFAOYSA-N 1-naphthaleneacetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CC=CC2=C1 PRPINYUDVPFIRX-UHFFFAOYSA-N 0.000 description 1
- LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 description 1
- FRPZMMHWLSIFAZ-UHFFFAOYSA-N 10-undecenoic acid Chemical compound OC(=O)CCCCCCCCC=C FRPZMMHWLSIFAZ-UHFFFAOYSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
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- 239000002035 hexane extract Substances 0.000 description 1
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 1
- 229960002591 hydroxyproline Drugs 0.000 description 1
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- 230000000236 ionophoric effect Effects 0.000 description 1
- YAQXGBBDJYBXKL-UHFFFAOYSA-N iron(2+);1,10-phenanthroline;dicyanide Chemical compound [Fe+2].N#[C-].N#[C-].C1=CN=C2C3=NC=CC=C3C=CC2=C1.C1=CN=C2C3=NC=CC=C3C=CC2=C1 YAQXGBBDJYBXKL-UHFFFAOYSA-N 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical group CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 1
- 238000007273 lactonization reaction Methods 0.000 description 1
- 230000001418 larval effect Effects 0.000 description 1
- 239000010501 lemon oil Substances 0.000 description 1
- 229940058352 levulinate Drugs 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 238000000622 liquid--liquid extraction Methods 0.000 description 1
- 239000003589 local anesthetic agent Substances 0.000 description 1
- 229960005015 local anesthetics Drugs 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 201000005249 lung adenocarcinoma Diseases 0.000 description 1
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- 239000003120 macrolide antibiotic agent Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000003550 marker Substances 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 201000001441 melanoma Diseases 0.000 description 1
- 239000000401 methanolic extract Substances 0.000 description 1
- XELZGAJCZANUQH-UHFFFAOYSA-N methyl 1-acetylthieno[3,2-c]pyrazole-5-carboxylate Chemical compound CC(=O)N1N=CC2=C1C=C(C(=O)OC)S2 XELZGAJCZANUQH-UHFFFAOYSA-N 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 210000000066 myeloid cell Anatomy 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 description 1
- 229960002446 octanoic acid Drugs 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 229940042126 oral powder Drugs 0.000 description 1
- 229940100692 oral suspension Drugs 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 229940015212 parid Drugs 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 238000004810 partition chromatography Methods 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 239000008023 pharmaceutical filler Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- AVRVZRUEXIEGMP-UHFFFAOYSA-N piperazine;hexahydrate Chemical compound O.O.O.O.O.O.C1CNCCN1 AVRVZRUEXIEGMP-UHFFFAOYSA-N 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229950008882 polysorbate Drugs 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 239000011253 protective coating Substances 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 210000000664 rectum Anatomy 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- JXOHGGNKMLTUBP-HSUXUTPPSA-N shikimic acid Chemical compound O[C@@H]1CC(C(O)=O)=C[C@@H](O)[C@H]1O JXOHGGNKMLTUBP-HSUXUTPPSA-N 0.000 description 1
- JXOHGGNKMLTUBP-JKUQZMGJSA-N shikimic acid Natural products O[C@@H]1CC(C(O)=O)=C[C@H](O)[C@@H]1O JXOHGGNKMLTUBP-JKUQZMGJSA-N 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000009491 slugging Methods 0.000 description 1
- 208000000587 small cell lung carcinoma Diseases 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000005031 thiocyano group Chemical group S(C#N)* 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- FGMPLJWBKKVCDB-UHFFFAOYSA-N trans-L-hydroxy-proline Natural products ON1CCCC1C(O)=O FGMPLJWBKKVCDB-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 238000013519 translation Methods 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 229960002703 undecylenic acid Drugs 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
- 201000005112 urinary bladder cancer Diseases 0.000 description 1
- 210000001215 vagina Anatomy 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000012431 wafers Nutrition 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/22—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains four or more hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Pyrane Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US44248782A | 1982-11-17 | 1982-11-17 | |
| US442487 | 1982-11-17 | ||
| US06/513,148 US4560774A (en) | 1982-11-17 | 1983-07-12 | Macrocyclic lactones |
| US513148 | 1990-04-23 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59108786A true JPS59108786A (ja) | 1984-06-23 |
| JPH0556357B2 JPH0556357B2 (https=) | 1993-08-19 |
Family
ID=27033183
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58215148A Granted JPS59108786A (ja) | 1982-11-17 | 1983-11-17 | ブリオスタチン類 |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US4560774A (https=) |
| EP (1) | EP0109811B1 (https=) |
| JP (1) | JPS59108786A (https=) |
| DE (1) | DE3363960D1 (https=) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63183585A (ja) * | 1986-07-28 | 1988-07-28 | アリゾナ ボ−ド オブ リ−ゼンツ | ブリオスタチン類 |
| JPH01308228A (ja) * | 1988-01-13 | 1989-12-12 | Univ Arizona Found | 免疫調整剤 |
Families Citing this family (46)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4611066A (en) * | 1984-08-10 | 1986-09-09 | Arizona State University | Bryostatins 4 to 8 |
| CA1291036C (en) * | 1986-04-23 | 1991-10-22 | Edwin I. Stoltz | Nasal administration of drugs |
| US5955501A (en) * | 1986-06-11 | 1999-09-21 | Procyon Pharmaceuticals, Inc. | Protein kinase C modulators O |
| US5716968A (en) * | 1986-06-11 | 1998-02-10 | Procyon Pharmaceuticals, Inc. | Protein kinase C modulators. H. |
| IL82811A0 (en) * | 1986-06-11 | 1987-12-20 | Alder Res Center Corp | Anti-inflammatory compositions containing methanol derivatives and novel compounds contained therein |
| US6043270A (en) * | 1986-06-11 | 2000-03-28 | Procyon Pharmaceuticals, Inc. | Protein kinase C modulators V |
| US5891906A (en) * | 1986-06-11 | 1999-04-06 | Procyon Pharmaceuticals, Inc. | Polyacetate-derived phorboids having anti-inflammatory and other uses |
| US5891870A (en) * | 1986-06-11 | 1999-04-06 | Procyon Pharmaceuticals, Inc. | Protein kinase C modulators Q |
| US5358711A (en) * | 1987-11-23 | 1994-10-25 | Johns Hopkins University | Stimulation of stem cell growth by the bryostatins |
| IT1229569B (it) * | 1989-04-17 | 1991-09-04 | Giuliani Spa | Derivati di acidi biliari, loro preparazione e composizioni farmaceutiche che li contengono. |
| US5072004A (en) * | 1990-12-31 | 1991-12-10 | Arizona Board Of Regents Acting On Behalf Of Arizona State University | Synthetic conversion of bryostatin 2 into bryostatin 1 |
| US5196447A (en) * | 1991-08-08 | 1993-03-23 | Arizona Board Of Regents, A Body Corporate Of The State Of Arizona, Acting On Behalf Of Arizona State University | Neristatin 1 |
| US5393897A (en) * | 1993-07-02 | 1995-02-28 | Arizona Board Of Regents Acting On Behalf Of Arizona State University | Isolation and structure of spongistatins 5,7,8 and 9 |
| US5684036A (en) * | 1994-02-18 | 1997-11-04 | Harbor Branch Oceanographic Institution, Inc. | Cytotoxic macrolides and methods of use |
| US5478861A (en) * | 1994-02-18 | 1995-12-26 | Harbor Branch Oceanographic Institution, Inc. | Cytotoxic macrolides and methods of use |
| US6060505A (en) * | 1996-03-20 | 2000-05-09 | The United States Of America As Represented By The Department Of Health And Human Services | Method of treating cancer using C-26 modified bryostatin |
| AU741439B2 (en) | 1996-12-30 | 2001-11-29 | Battelle Memorial Institute | Formulation and method for treating neoplasms by inhalation |
| AUPO864097A0 (en) * | 1997-08-19 | 1997-09-11 | Peplin Pty Ltd | Anti-cancer compounds |
| US6221153B1 (en) * | 1998-06-09 | 2001-04-24 | Trevor Percival Castor | Method for producing large crystals of complex molecules |
| US7256286B2 (en) * | 1999-11-30 | 2007-08-14 | The Board Of Trustees Of The Leland Stanford Junior University | Bryostatin analogues, synthetic methods and uses |
| AU784589B2 (en) * | 1999-11-30 | 2006-05-04 | Board Of Trustees Of The Leland Stanford Junior University | Bryostatin analogues, synthetic methods and uses |
| AUPQ801700A0 (en) * | 2000-06-07 | 2000-06-29 | Peplin Research Pty Ltd | Enzyme and viral activation |
| AUPQ923100A0 (en) | 2000-08-07 | 2000-08-31 | Peplin Research Pty Ltd | Treatment of prostate cancer |
| ES2314056T3 (es) * | 2001-05-02 | 2009-03-16 | Blanchette Rockefeller Neurosciences Institute | Activadores de la anhidrasa carbonica para mejorar el aprendizaje y la memoria. |
| US6825229B2 (en) | 2002-03-07 | 2004-11-30 | Blanchette Rockefeller Neurosciences Institute | Methods for Alzheimer's Disease treatment and cognitive enhancement |
| US20080004332A1 (en) * | 2002-03-07 | 2008-01-03 | Alkon Daniel L | Methods for alzheimer's disease treatment and cognitive enhancement |
| US20050065205A1 (en) * | 2002-03-07 | 2005-03-24 | Daniel Alkon | Methods for Alzheimer's disease treatment and cognitive enhance |
| TW201206425A (en) | 2004-05-18 | 2012-02-16 | Brni Neurosciences Inst | Treatment of depressive disorders |
| CA2589992C (en) * | 2004-12-13 | 2014-04-22 | Peplin Research Pty Ltd | Treatment of solid cancers |
| US20070054890A1 (en) | 2005-07-29 | 2007-03-08 | Alkon Daniel L | Protein synthesis required for long-term memory is induced by PKC activation on days preceding associative learning |
| KR20080077625A (ko) * | 2005-11-25 | 2008-08-25 | 페플린 리서치 피티이 리미티드 | 상처 치유 방법 |
| US20080025961A1 (en) | 2006-07-28 | 2008-01-31 | Alkon Daniel L | Methods of stimulating cellular growth, synaptic remodeling and consolidation of long-term memory |
| EP3332797A3 (en) | 2007-02-09 | 2018-08-01 | Blanchette Rockefeller Neurosciences Institute | Therapeutic effects of bryostatins, bryologs and other related substances on head trauma-induced memory impairment and brain injury |
| WO2008100450A2 (en) | 2007-02-09 | 2008-08-21 | Blanchette Rockefeller Neurosciences Institute | Therapeutic effects of bryostatins, bryologs, and other related substances on ischemia/stroke-induced memory impairment and brain injury |
| US9994585B2 (en) | 2007-12-31 | 2018-06-12 | Aphios Corporation | Transplantation therapies |
| US20120027687A1 (en) | 2010-07-08 | 2012-02-02 | Alkon Daniel L | Fatty acid protein kinase c activators and anticoagulant for the treatment of stroke |
| EP2605773A1 (en) | 2010-08-19 | 2013-06-26 | Blanchette Rockefeller Neurosciences, Institute | Treatment of cognitive disorders associated with abnormal dendritic spines using pkc activators |
| CA2855932A1 (en) | 2011-11-13 | 2013-05-16 | Blanchette Rockefeller Neurosciences Institute | Pkc activators and combinations thereof |
| US9034347B2 (en) | 2011-12-19 | 2015-05-19 | Arphios Corporation | Drug delivery system and method for the treatment of neuro-degenerative disease |
| CN105228614A (zh) | 2012-11-28 | 2016-01-06 | 阿菲欧斯公司 | 用于治疗神经退化疾病和其它疾病的组合治疗剂和方法 |
| WO2016130969A1 (en) | 2015-02-13 | 2016-08-18 | George Robert Pettit | Silstatin compounds |
| US20180217163A1 (en) | 2015-05-11 | 2018-08-02 | Daniel L. Alkon | Treatment of neurodegenerative conditions using pkc activators after determining the presence of the apoe4 allele |
| US11123324B2 (en) | 2016-08-18 | 2021-09-21 | Noster Inc. | Immunomodulator |
| WO2018187647A1 (en) | 2017-04-06 | 2018-10-11 | Neurotrope Bioscience, Inc. | Methods and compositions for treatment of neurological diseases, disorders, or conditions |
| WO2019094709A1 (en) | 2017-11-09 | 2019-05-16 | Pettit George R | Betulastatin compounds |
| EP3793543A1 (en) | 2018-05-18 | 2021-03-24 | Neurotrope Bioscience, Inc. | Methods and compositions for treatment of alzheimer's disease |
-
1983
- 1983-07-12 US US06/513,148 patent/US4560774A/en not_active Expired - Lifetime
- 1983-11-11 EP EP83306896A patent/EP0109811B1/en not_active Expired
- 1983-11-11 DE DE8383306896T patent/DE3363960D1/de not_active Expired
- 1983-11-17 JP JP58215148A patent/JPS59108786A/ja active Granted
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63183585A (ja) * | 1986-07-28 | 1988-07-28 | アリゾナ ボ−ド オブ リ−ゼンツ | ブリオスタチン類 |
| JPH01308228A (ja) * | 1988-01-13 | 1989-12-12 | Univ Arizona Found | 免疫調整剤 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0109811B1 (en) | 1986-06-04 |
| US4560774A (en) | 1985-12-24 |
| EP0109811A2 (en) | 1984-05-30 |
| JPH0556357B2 (https=) | 1993-08-19 |
| EP0109811A3 (en) | 1984-07-11 |
| DE3363960D1 (en) | 1986-07-10 |
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