JP2015504096A5 - - Google Patents
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- Publication number
- JP2015504096A5 JP2015504096A5 JP2014553497A JP2014553497A JP2015504096A5 JP 2015504096 A5 JP2015504096 A5 JP 2015504096A5 JP 2014553497 A JP2014553497 A JP 2014553497A JP 2014553497 A JP2014553497 A JP 2014553497A JP 2015504096 A5 JP2015504096 A5 JP 2015504096A5
- Authority
- JP
- Japan
- Prior art keywords
- phorbol
- deoxyphorbol
- acetate
- formula
- ester
- 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
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- PHEDXBVPIONUQT-RGYGYFBISA-N phorbol 13-acetate 12-myristate Chemical compound C([C@]1(O)C(=O)C(C)=C[C@H]1[C@@]1(O)[C@H](C)[C@H]2OC(=O)CCCCCCCCCCCCC)C(CO)=C[C@H]1[C@H]1[C@]2(OC(C)=O)C1(C)C PHEDXBVPIONUQT-RGYGYFBISA-N 0.000 claims description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- 239000001257 hydrogen Substances 0.000 claims description 24
- 239000002644 phorbol ester Substances 0.000 claims description 21
- 239000000203 mixture Substances 0.000 claims description 18
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 16
- 230000000694 effects Effects 0.000 claims description 11
- GZNWHPFWQMQXII-UHFFFAOYSA-N 1-(2-ethylphenyl)pyrrole-2,5-dione Chemical compound CCC1=CC=CC=C1N1C(=O)C=CC1=O GZNWHPFWQMQXII-UHFFFAOYSA-N 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- NUQJULCGNZMBEF-UHFFFAOYSA-N Prostratin Natural products COC(=O)C12CC(C)C3(O)C(C=C(CO)CC4(O)C3C=C(C)C4=O)C1C2(C)C NUQJULCGNZMBEF-UHFFFAOYSA-N 0.000 claims description 5
- VCQRVYCLJARKLE-XQOWHXTBSA-N (1ar,1bs,4ar,7as,7bs,8r,9r,9as)-3-[(acetyloxy)methyl]-4a,7b,9-trihydroxy-1,1,6,8-tetramethyl-5-oxo-1,1a,1b,4,4a,5,7a,7b,8,9-decahydro-9ah-cyclopropa[3,4]benzo[1,2-e]azulen-9a-yl acetate Chemical compound C1=C(COC(C)=O)C[C@]2(O)C(=O)C(C)=C[C@H]2[C@@]2(O)[C@H](C)[C@@H](O)[C@@]3(OC(C)=O)C(C)(C)[C@H]3[C@@H]21 VCQRVYCLJARKLE-XQOWHXTBSA-N 0.000 claims description 4
- CBDIJHBGVGPIIE-MCDHERAVSA-N 1,1a,1b,4,4a,7a,7b,8,9,9a-decahydro-4a,7b,9a-trihydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-,(1ar,1bs,4ar,7as,7br,8r,9as)-5h-cyclopropa(3,4)benz(1,2-e)azulen-5-one Chemical compound C1=C(CO)C[C@]2(O)C(=O)C(C)=C[C@H]2[C@@]2(O)[C@H](C)C[C@@]3(O)C(C)(C)[C@H]3[C@@H]21 CBDIJHBGVGPIIE-MCDHERAVSA-N 0.000 claims description 4
- HJEHMBCPVHLCOG-UHFFFAOYSA-N 1-ethynyl-4-propan-2-yloxybenzene Chemical compound CC(C)OC1=CC=C(C#C)C=C1 HJEHMBCPVHLCOG-UHFFFAOYSA-N 0.000 claims description 4
- GFAGCYRBGVCTPP-UHFFFAOYSA-N 12-deoxyphorbol 13-angelate Natural products C1C(C)C2(O)C3C=C(C)C(=O)C3(O)CC(CO)=CC2C2C1(OC(=O)C(C)=CC)C2(C)C GFAGCYRBGVCTPP-UHFFFAOYSA-N 0.000 claims description 4
- GFAGCYRBGVCTPP-APZZYBINSA-N 12-deoxyphorbol-13-angelate Chemical compound C([C@]1(O)C(=O)C(C)=C[C@H]1[C@@]1(O)[C@H](C)C2)C(CO)=C[C@H]1[C@H]1[C@]2(OC(=O)C(\C)=C/C)C1(C)C GFAGCYRBGVCTPP-APZZYBINSA-N 0.000 claims description 4
- QSTFRCUXCBXJAW-UHFFFAOYSA-N 12-deoxyphorbol-13-isobutyrate Natural products C1C(C)C2(O)C3C=C(C)C(=O)C3(O)CC(CO)=CC2C2C1(OC(=O)C(C)C)C2(C)C QSTFRCUXCBXJAW-UHFFFAOYSA-N 0.000 claims description 4
- ZZTJICHINNSOQL-LWYYLCCUSA-N 12-deoxyphorbol-13-tiglate-20-acetate Chemical compound C([C@]1(O)C(=O)C(C)=C[C@H]1[C@@]1(O)[C@H](C)C2)C(COC(C)=O)=C[C@H]1[C@H]1[C@]2(OC(=O)C(/C)=C/C)C1(C)C ZZTJICHINNSOQL-LWYYLCCUSA-N 0.000 claims description 4
- SDSVJYOOAPRSDA-RPCQODIISA-N 13-Acetylphorbol Chemical compound C1=C(CO)C[C@]2(O)C(=O)C(C)=C[C@H]2[C@@]2(O)[C@H](C)[C@@H](O)[C@@]3(OC(C)=O)C(C)(C)[C@H]3[C@@H]21 SDSVJYOOAPRSDA-RPCQODIISA-N 0.000 claims description 4
- NQSPTMFCJGKOQJ-UHFFFAOYSA-N 2,2,2-trifluoro-1-(3-fluorophenyl)ethanone Chemical compound FC1=CC=CC(C(=O)C(F)(F)F)=C1 NQSPTMFCJGKOQJ-UHFFFAOYSA-N 0.000 claims description 4
- MGWGTDCOSWKYIL-UHFFFAOYSA-N 2-amino-4-(diaminomethylideneamino)butanoic acid;hydrochloride Chemical compound Cl.OC(=O)C(N)CCN=C(N)N MGWGTDCOSWKYIL-UHFFFAOYSA-N 0.000 claims description 4
- QWYNFKKVBDGBLL-UBDSXHIHSA-N Phorbol 12-tiglate 13-decanoate Natural products O=C(O[C@H]1[C@@H](C)[C@@]2(O)[C@H]3[C@@](O)(C(=O)C(C)=C3)CC(CO)=C[C@H]2[C@H]2C(C)(C)[C@]12OC(=O)CCCCCCCCC)/C(=C\C)/C QWYNFKKVBDGBLL-UBDSXHIHSA-N 0.000 claims description 4
- YJFFPVQHOKPCRV-LKSXOGJWSA-N [(1S,2S,6R,10S,11R,13S,14R,15R)-1,6,14-trihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxo-13-tetracyclo[8.5.0.02,6.011,13]pentadeca-3,8-dienyl] decanoate Chemical compound C1=C(CO)C[C@]2(O)C(=O)C(C)=C[C@H]2[C@@]2(O)[C@H](C)[C@@H](O)[C@@]3(OC(=O)CCCCCCCCC)C(C)(C)[C@H]3[C@@H]21 YJFFPVQHOKPCRV-LKSXOGJWSA-N 0.000 claims description 4
- CESGKXMBHGUQTB-VONOSFMSSA-N [(1S,2S,6R,10S,11R,13S,14R,15R)-1,6,14-trihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxo-13-tetracyclo[8.5.0.02,6.011,13]pentadeca-3,8-dienyl] tetradecanoate Chemical compound C1=C(CO)C[C@]2(O)C(=O)C(C)=C[C@H]2[C@@]2(O)[C@H](C)[C@@H](O)[C@@]3(OC(=O)CCCCCCCCCCCCC)C(C)(C)[C@H]3[C@@H]21 CESGKXMBHGUQTB-VONOSFMSSA-N 0.000 claims description 4
- LMLOFRDITXUVHZ-BPNNYVJBSA-N ac1l3xbq Chemical compound C([C@]1(O)C(=O)C(C)=C[C@H]1[C@@]1(O)[C@H](C)[C@H]2OC(=O)CC)C(CO)=C[C@H]1[C@H]1[C@]2(OC(=O)CC)C1(C)C LMLOFRDITXUVHZ-BPNNYVJBSA-N 0.000 claims description 4
- LASMKIAVFGUYEG-SEYWVDNQSA-N phorbol 12,13,20-triacetate Chemical compound C1=C(COC(C)=O)C[C@]2(O)C(=O)C(C)=C[C@H]2[C@@]2(O)[C@H](C)[C@@H](OC(C)=O)[C@@]3(OC(C)=O)C(C)(C)[C@H]3[C@@H]21 LASMKIAVFGUYEG-SEYWVDNQSA-N 0.000 claims description 4
- BQJRUJTZSGYBEZ-YVQNUNKESA-N phorbol 12,13-dibutanoate Chemical compound C([C@]1(O)C(=O)C(C)=C[C@H]1[C@@]1(O)[C@H](C)[C@H]2OC(=O)CCC)C(CO)=C[C@H]1[C@H]1[C@]2(OC(=O)CCC)C1(C)C BQJRUJTZSGYBEZ-YVQNUNKESA-N 0.000 claims description 4
- NVKVYBPQQUTLSY-RPCQODIISA-N phorbol 12-acetate Chemical compound C1=C(CO)C[C@]2(O)C(=O)C(C)=C[C@H]2[C@@]2(O)[C@H](C)[C@@H](OC(C)=O)[C@@]3(O)C(C)(C)[C@H]3[C@@H]21 NVKVYBPQQUTLSY-RPCQODIISA-N 0.000 claims description 4
- LXYSVTVLQYLWKR-LKSXOGJWSA-N phorbol 12-decanoate Chemical compound C([C@]1(O)C(=O)C(C)=C[C@H]1[C@@]1(O)[C@H](C)[C@H]2OC(=O)CCCCCCCCC)C(CO)=C[C@H]1[C@H]1[C@]2(O)C1(C)C LXYSVTVLQYLWKR-LKSXOGJWSA-N 0.000 claims description 4
- FZXHDWWEDNRATG-JUDMOCROSA-N phorbol 13-butanoate Chemical group C1=C(CO)C[C@]2(O)C(=O)C(C)=C[C@H]2[C@@]2(O)[C@H](C)[C@@H](O)[C@@]3(OC(=O)CCC)C(C)(C)[C@H]3[C@@H]21 FZXHDWWEDNRATG-JUDMOCROSA-N 0.000 claims description 4
- QWYNFKKVBDGBLL-KFWZAFQTSA-N phorbol 13-decanoate 12-tiglate Chemical compound C1=C(CO)C[C@]2(O)C(=O)C(C)=C[C@H]2[C@@]2(O)[C@H](C)[C@@H](OC(=O)C(\C)=C\C)[C@@]3(OC(=O)CCCCCCCCC)C(C)(C)[C@H]3[C@@H]21 QWYNFKKVBDGBLL-KFWZAFQTSA-N 0.000 claims description 4
- DGOSGFYDFDYMCW-MWRBZVGOSA-N phorbol dicaprate Chemical compound C([C@]1(O)C(=O)C(C)=C[C@H]1[C@@]1(O)[C@H](C)[C@H]2OC(=O)CCCCCCCCC)C(CO)=C[C@H]1[C@H]1[C@]2(OC(=O)CCCCCCCCC)C1(C)C DGOSGFYDFDYMCW-MWRBZVGOSA-N 0.000 claims description 4
- XGPRSRGBAHBMAF-NQWCLMGHSA-N phorbol-12,13-dihexanoate Chemical compound C([C@]1(O)C(=O)C(C)=C[C@H]1[C@@]1(O)[C@H](C)[C@H]2OC(=O)CCCCC)C(CO)=C[C@H]1[C@H]1[C@]2(OC(=O)CCCCC)C1(C)C XGPRSRGBAHBMAF-NQWCLMGHSA-N 0.000 claims description 4
- XLCISDOVNFLSGO-VONOSFMSSA-N phorbol-12-myristate Chemical compound C([C@]1(O)C(=O)C(C)=C[C@H]1[C@@]1(O)[C@H](C)[C@H]2OC(=O)CCCCCCCCCCCCC)C(CO)=C[C@H]1[C@H]1[C@]2(O)C1(C)C XLCISDOVNFLSGO-VONOSFMSSA-N 0.000 claims description 4
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 3
- 238000009472 formulation Methods 0.000 claims description 3
- 230000002265 prevention Effects 0.000 claims description 3
- 238000011282 treatment Methods 0.000 claims description 3
- -1 antiplatelet agent Substances 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims 15
- 208000006011 Stroke Diseases 0.000 claims 12
- 238000004519 manufacturing process Methods 0.000 claims 6
- 229940124597 therapeutic agent Drugs 0.000 claims 6
- 238000011269 treatment regimen Methods 0.000 claims 6
- 230000006735 deficit Effects 0.000 claims 5
- 238000009098 adjuvant therapy Methods 0.000 claims 4
- 239000005541 ACE inhibitor Substances 0.000 claims 3
- 102000008873 Angiotensin II receptor Human genes 0.000 claims 3
- 108050000824 Angiotensin II receptor Proteins 0.000 claims 3
- 101710129690 Angiotensin-converting enzyme inhibitor Proteins 0.000 claims 3
- 101710086378 Bradykinin-potentiating and C-type natriuretic peptides Proteins 0.000 claims 3
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims 3
- FDFRQMKAXPLXFL-UZAJRZOCSA-N ac1l576h Chemical compound C([C@]1(O)C(=O)C(C)=C[C@H]1[C@@]1(O)[C@H](C)C2)C(CO)=C[C@H]1[C@H]1[C@]2(OC(=O)CCCCCCCCCCCCC)C1(C)C FDFRQMKAXPLXFL-UZAJRZOCSA-N 0.000 claims 3
- 229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 claims 3
- 239000003146 anticoagulant agent Substances 0.000 claims 3
- 229940127219 anticoagulant drug Drugs 0.000 claims 3
- 229940127218 antiplatelet drug Drugs 0.000 claims 3
- 239000002876 beta blocker Substances 0.000 claims 3
- 229940097320 beta blocking agent Drugs 0.000 claims 3
- RTJAYUGZUOLFMY-UHFFFAOYSA-N deoxyphorbol Natural products C1=C(CO)CC2C(=O)C(C)=CC2C2(O)C(C)C(O)C3(O)C(C)(C)C3C21 RTJAYUGZUOLFMY-UHFFFAOYSA-N 0.000 claims 3
- 239000002934 diuretic Substances 0.000 claims 3
- 230000001882 diuretic effect Effects 0.000 claims 3
- 229940125753 fibrate Drugs 0.000 claims 3
- 239000003087 receptor blocking agent Substances 0.000 claims 3
- 208000000044 Amnesia Diseases 0.000 claims 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims 2
- 108091006146 Channels Proteins 0.000 claims 2
- 208000028698 Cognitive impairment Diseases 0.000 claims 2
- 208000026139 Memory disease Diseases 0.000 claims 2
- 206010028813 Nausea Diseases 0.000 claims 2
- 206010033799 Paralysis Diseases 0.000 claims 2
- 102000003978 Tissue Plasminogen Activator Human genes 0.000 claims 2
- 108090000373 Tissue Plasminogen Activator Proteins 0.000 claims 2
- 206010047700 Vomiting Diseases 0.000 claims 2
- 239000002671 adjuvant Substances 0.000 claims 2
- 201000007201 aphasia Diseases 0.000 claims 2
- 239000011575 calcium Substances 0.000 claims 2
- 229910052791 calcium Inorganic materials 0.000 claims 2
- 229960005069 calcium Drugs 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 208000010877 cognitive disease Diseases 0.000 claims 2
- 150000002148 esters Chemical class 0.000 claims 2
- 230000006984 memory degeneration Effects 0.000 claims 2
- 208000023060 memory loss Diseases 0.000 claims 2
- 230000008693 nausea Effects 0.000 claims 2
- 230000001953 sensory effect Effects 0.000 claims 2
- 238000011477 surgical intervention Methods 0.000 claims 2
- 229960000187 tissue plasminogen activator Drugs 0.000 claims 2
- 230000008673 vomiting Effects 0.000 claims 2
- 229940127291 Calcium channel antagonist Drugs 0.000 claims 1
- 229940097420 Diuretic Drugs 0.000 claims 1
- 208000008883 Patent Foramen Ovale Diseases 0.000 claims 1
- 238000002399 angioplasty Methods 0.000 claims 1
- 239000000480 calcium channel blocker Substances 0.000 claims 1
- 238000013172 carotid endarterectomy Methods 0.000 claims 1
- 210000004351 coronary vessel Anatomy 0.000 claims 1
- 238000007428 craniotomy Methods 0.000 claims 1
- 230000010102 embolization Effects 0.000 claims 1
- 230000007027 foramen ovale closure Effects 0.000 claims 1
- 238000002513 implantation Methods 0.000 claims 1
- 230000037431 insertion Effects 0.000 claims 1
- 238000003780 insertion Methods 0.000 claims 1
- 238000001356 surgical procedure Methods 0.000 claims 1
- 238000002054 transplantation Methods 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 150000002431 hydrogen Chemical class 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 5
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 229940002612 prodrug Drugs 0.000 description 3
- 239000000651 prodrug Substances 0.000 description 3
- 239000012453 solvate Substances 0.000 description 3
- PHEDXBVPIONUQT-UHFFFAOYSA-N Cocarcinogen A1 Natural products CCCCCCCCCCCCCC(=O)OC1C(C)C2(O)C3C=C(C)C(=O)C3(O)CC(CO)=CC2C2C1(OC(C)=O)C2(C)C PHEDXBVPIONUQT-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 150000004633 phorbol derivatives Chemical class 0.000 description 2
- QGVLYPPODPLXMB-UBTYZVCOSA-N (1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-4a,7b,9,9a-tetrahydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-1,1a,1b,4,4a,7a,7b,8,9,9a-decahydro-5H-cyclopropa[3,4]benzo[1,2-e]azulen-5-one Chemical compound C1=C(CO)C[C@]2(O)C(=O)C(C)=C[C@H]2[C@@]2(O)[C@H](C)[C@@H](O)[C@@]3(O)C(C)(C)[C@H]3[C@@H]21 QGVLYPPODPLXMB-UBTYZVCOSA-N 0.000 description 1
- MTXOHECJOIIIJM-PHFLZNSYSA-N 12-deoxyphorbol-13-isobutyrate-20-acetate Chemical compound C([C@]1(O)C(=O)C(C)=C[C@H]1[C@@]1(O)[C@H](C)C2)C(COC(C)=O)=C[C@H]1[C@H]1[C@]2(OC(=O)C(C)C)C1(C)C MTXOHECJOIIIJM-PHFLZNSYSA-N 0.000 description 1
- MTXOHECJOIIIJM-UHFFFAOYSA-N 12-deoxyphorbol-13-isobutyrate-20-acetate Natural products C1C(C)C2(O)C3C=C(C)C(=O)C3(O)CC(COC(C)=O)=CC2C2C1(OC(=O)C(C)C)C2(C)C MTXOHECJOIIIJM-UHFFFAOYSA-N 0.000 description 1
- 244000168525 Croton tiglium Species 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 230000005754 cellular signaling Effects 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 229940117173 croton oil Drugs 0.000 description 1
- 229930004069 diterpene Natural products 0.000 description 1
- 125000000567 diterpene group Chemical group 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- QGVLYPPODPLXMB-QXYKVGAMSA-N phorbol Natural products C[C@@H]1[C@@H](O)[C@]2(O)[C@H]([C@H]3C=C(CO)C[C@@]4(O)[C@H](C=C(C)C4=O)[C@@]13O)C2(C)C QGVLYPPODPLXMB-QXYKVGAMSA-N 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- BOJKFRKNLSCGHY-HXGSDTCMSA-N prostratin Chemical compound C1=C(CO)C[C@]2(O)C(=O)C(C)=C[C@H]2[C@@]2(O)[C@H](C)C[C@@]3(OC(C)=O)C(C)(C)[C@H]3[C@@H]21 BOJKFRKNLSCGHY-HXGSDTCMSA-N 0.000 description 1
- 230000000306 recurrent effect Effects 0.000 description 1
- CGVXVPQJMYMMIH-HKDZDBKOSA-N tigliane Chemical compound C1[C@H](C)C[C@H]2[C@@H]3C(C)(C)[C@@H]3C[C@@H](C)[C@@H]2[C@@H]2C[C@H](C)C[C@H]21 CGVXVPQJMYMMIH-HKDZDBKOSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261588162P | 2012-01-18 | 2012-01-18 | |
| US201261588167P | 2012-01-18 | 2012-01-18 | |
| US201261588165P | 2012-01-18 | 2012-01-18 | |
| US61/588,167 | 2012-01-18 | ||
| US61/588,165 | 2012-01-18 | ||
| US61/588,162 | 2012-01-18 | ||
| PCT/US2013/022325 WO2014011209A1 (en) | 2012-01-18 | 2013-01-18 | Compositions and methods of use of phorbol esters for the treatment of stroke |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018019844A Division JP6715871B2 (ja) | 2012-01-18 | 2018-02-07 | 脳卒中の治療のためのホルボールエステルの組成物および使用方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2015504096A JP2015504096A (ja) | 2015-02-05 |
| JP2015504096A5 true JP2015504096A5 (OSRAM) | 2016-01-28 |
| JP6336914B2 JP6336914B2 (ja) | 2018-06-06 |
Family
ID=48799818
Family Applications (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014553497A Active JP6336914B2 (ja) | 2012-01-18 | 2013-01-18 | 脳卒中の治療のためのホルボールエステルの組成物および使用方法 |
| JP2014553496A Active JP6463969B2 (ja) | 2012-01-18 | 2013-01-18 | ホルボールエステルの組成物およびその使用方法 |
| JP2018019844A Active JP6715871B2 (ja) | 2012-01-18 | 2018-02-07 | 脳卒中の治療のためのホルボールエステルの組成物および使用方法 |
| JP2018153583A Active JP6835778B2 (ja) | 2012-01-18 | 2018-08-17 | ホルボールエステルの組成物およびその使用方法 |
| JP2021016689A Pending JP2021073288A (ja) | 2012-01-18 | 2021-02-04 | ホルボールエステルの組成物およびその使用方法 |
Family Applications After (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014553496A Active JP6463969B2 (ja) | 2012-01-18 | 2013-01-18 | ホルボールエステルの組成物およびその使用方法 |
| JP2018019844A Active JP6715871B2 (ja) | 2012-01-18 | 2018-02-07 | 脳卒中の治療のためのホルボールエステルの組成物および使用方法 |
| JP2018153583A Active JP6835778B2 (ja) | 2012-01-18 | 2018-08-17 | ホルボールエステルの組成物およびその使用方法 |
| JP2021016689A Pending JP2021073288A (ja) | 2012-01-18 | 2021-02-04 | ホルボールエステルの組成物およびその使用方法 |
Country Status (18)
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| JP (5) | JP6336914B2 (OSRAM) |
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| AU (7) | AU2013287280B2 (OSRAM) |
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| AU2008211081A1 (en) | 2007-01-31 | 2008-08-07 | Biosuccess Biotech Company | Compositions and methods of use of phorbol esters |
| US11696908B2 (en) | 2007-01-31 | 2023-07-11 | Biosuccess Biotech Co. Ltd. | Compositions and methods of use of phorbol esters |
| US10369222B2 (en) | 2012-01-18 | 2019-08-06 | Biosuccess Biotech Co., Ltd. | Compositions and methods of use of phorbol esters for the treatment of stroke |
| US11564901B2 (en) | 2007-01-31 | 2023-01-31 | Biosuccess Biotech Co., Ltd. | Compositions and methods of use of phorbol esters |
| US9974764B2 (en) | 2007-01-31 | 2018-05-22 | Biosuccess Biotech Co. Ltd. | Compositions and methods of use of phorbol esters in the treatment of neoplasms |
| US9533938B2 (en) | 2007-01-31 | 2017-01-03 | Biosuccess Biotech Co., Ltd. | Compositions and methods of use of phorbol esters for the treatment of stroke |
| US9636317B2 (en) | 2007-01-31 | 2017-05-02 | Biosuccess Biotech Co. Ltd. | Compositions and methods of use of phorbol esters |
| US9550722B2 (en) | 2012-01-18 | 2017-01-24 | Biosuccess Biotech Co. Ltd. | Compositions and methods of use of phorbal esters for the treatment of stroke |
| US10099996B2 (en) | 2012-01-18 | 2018-10-16 | Biosuccess Biotech Co. Ltd. | Compositions and methods of use of phorbol esters in the treatment of neoplasms |
| SG10201912642RA (en) * | 2012-01-18 | 2020-02-27 | Biosuccess Biotech Co Ltd | Compositions and methods of use of phorbol esters |
| TWI687217B (zh) * | 2014-01-10 | 2020-03-11 | 華鴻新藥股份有限公司 | 用於中風治療之巴豆酯組成物及使用方法 |
| NZ724799A (en) * | 2014-04-16 | 2023-07-28 | Sujon Pty Ltd | Compositions and methods for the treatment or prevention of neurodegenerative disorders |
| JP2017527583A (ja) | 2014-09-10 | 2017-09-21 | ザ リージェンツ オブ ザ ユニバーシティ オブ カリフォルニア | Ｋ−Ｒａｓによって媒介されるシグナリング経路および悪性疾患のプロストラチンによるターゲティング方法 |
| MA40904A (fr) * | 2014-11-03 | 2017-09-12 | Hygeia Tech Inc | Compositions d'ester de phorbol et procédés pour traiter ou réduire la durée d'une cytopénie |
| WO2016122288A2 (ko) * | 2015-01-30 | 2016-08-04 | 고려대학교산학협력단 | 베르베논 유도체 및 재관류 치료제를 포함하는 뇌혈관 질환, 동맥경화증 또는 심혈관 질환 치료 또는 예방용 병용 제제 |
| KR20160107426A (ko) | 2015-03-04 | 2016-09-19 | 임세영 | 구두 굽 및 그 제조방법 |
| KR101710674B1 (ko) * | 2015-07-22 | 2017-02-27 | 가톨릭대학교 산학협력단 | Epo 수용체 및 pkc 동시 표적물질을 유효성분으로 포함하는 빈혈의 예방 또는 치료용 약학 조성물 및 이의 용도 |
| CN106420687A (zh) * | 2016-10-11 | 2017-02-22 | 孙君重 | 防护肠辐射损伤的方法及tpa的用途 |
| KR102059160B1 (ko) * | 2017-11-15 | 2019-12-24 | 한국생명공학연구원 | 다프난 또는 포볼 다이터펜계 화합물을 포함하는 신경퇴행성 질환 예방 또는 치료용 조성물 |
| CA3084139C (en) * | 2017-11-15 | 2023-02-28 | Korea Research Institute Of Bioscience And Biotechnology | Composition for preventing or treating neurodegenerative diseases, containing diterpene-based compound |
| CN108689851B (zh) * | 2018-05-28 | 2020-04-17 | 中山大学 | 一类惕各烷型二萜化合物及其制备方法和应用 |
| WO2021062030A1 (en) * | 2019-09-24 | 2021-04-01 | K-Gen, Inc. | Diterpenoid compounds that act on protein kinase c (pkc) |
| KR102541582B1 (ko) * | 2020-10-29 | 2023-06-12 | 가톨릭관동대학교산학협력단 | 13-ｏ-아세틸포볼을 포함하는 골질환 및 혈관석회화증 예방 또는 치료용 약학적 조성물 |
| WO2022092884A1 (ko) * | 2020-10-29 | 2022-05-05 | 가톨릭관동대학교산학협력단 | 13-ｏ-아세틸포볼을 포함하는 골질환 및 혈관석회화증 예방 또는 치료용 약학적 조성물 |
| CN112715542A (zh) * | 2021-01-20 | 2021-04-30 | 沈阳农业大学 | 巴豆烷二萜类化合物的制备方法及其在制备杀线虫的杀虫剂中的应用 |
| CN116159126A (zh) * | 2022-12-31 | 2023-05-26 | 山东大学齐鲁医院 | 同源二聚体介导的C/EBPαS16磷酸化通过液-液相分离调节急性髓系白血病分化 |
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| US2375308A (en) | 1942-08-21 | 1945-05-08 | Ibm | Method of making stencil cards |
| US5241051A (en) * | 1992-04-24 | 1993-08-31 | Research Development Foundation | Oncoinhibin |
| US6043224A (en) * | 1996-09-05 | 2000-03-28 | The Massachusetts Institute Of Technology | Compositions and methods for treatment of neurological disorders and neurodegenerative diseases |
| US6184248B1 (en) * | 1996-09-05 | 2001-02-06 | Robert K. K. Lee | Compositions and methods for treatment of neurological disorders and neurodegenerative diseases |
| US6063814A (en) * | 1997-04-14 | 2000-05-16 | Chang; Richard L. | Phorbol esters as anti-neoplastic and white blood cell elevating agents |
| US20070009529A1 (en) * | 2002-03-26 | 2007-01-11 | New York University | Agents that dissolve arterial thrombi |
| WO2002083877A1 (en) * | 2001-04-11 | 2002-10-24 | Stem Cell Therapeutics Inc. | Production of tyrosine hydroxylase positive neurons |
| US20080004332A1 (en) * | 2002-03-07 | 2008-01-03 | Alkon Daniel L | Methods for alzheimer's disease treatment and cognitive enhancement |
| DE10244453A1 (de) * | 2002-09-24 | 2004-04-01 | Phenomiques Gmbh | Hemmung der Proteinkinase C-alpha zur Behandlung von Krankheiten |
| CA2614110A1 (en) * | 2005-07-01 | 2007-01-11 | The Johns Hopkins University | Compositions and methods for the treatment or prevention of disorders relating to oxidative stress |
| AU2008211081A1 (en) * | 2007-01-31 | 2008-08-07 | Biosuccess Biotech Company | Compositions and methods of use of phorbol esters |
| WO2009151496A2 (en) * | 2008-03-26 | 2009-12-17 | The Government Of The United States Of America, As Represented By The Secretary, Department Of Health & Human Services, | Induction of proliferation, effector molecule expression, and cytolytic capacity of hiv-specific cd8+ t cells |
| EP2331088A4 (en) * | 2008-08-06 | 2011-10-12 | Gosforth Ct Holdings Pty Ltd | COMPOSITIONS AND METHODS FOR TREATING PSYCHIATRIC ILLNESSES |
| EP2362770A4 (en) * | 2008-11-21 | 2012-05-30 | Univ Johns Hopkins | COMPOSITIONS AND METHODS FOR TREATING OR PREVENTING RADIATION DAMAGE |
| RU2426535C2 (ru) * | 2009-05-15 | 2011-08-20 | Маргарита Алексеевна Морозова | Применение бета-гидроксибутирата или его фармацевтически приемлемых солей для приготовления лекарственного средства, обладающего цитопротекторной активностью, включающей нейропротекторную, кардиопротекторную, противоишемическую, антигипоксическую, антистрессорную, актопротекторную и адаптогенную активности, лекарственное средство и способ профилактики, купирования и лечения с помощью этого лекарственного средства |
| US8575216B2 (en) * | 2009-08-04 | 2013-11-05 | Rutgers, The State University Of New Jersey | Method of treatment for acute myelogenous leukemia |
| KR101144327B1 (ko) * | 2010-04-02 | 2012-05-11 | 한국과학기술연구원 | Ｐｋｃ 작용 활성제를 유효성분으로 함유하는 압상스 간질의 예방 및 치료용 조성물 |
| SG10201912642RA (en) * | 2012-01-18 | 2020-02-27 | Biosuccess Biotech Co Ltd | Compositions and methods of use of phorbol esters |
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