JP2012500271A5 - - Google Patents
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- JP2012500271A5 JP2012500271A5 JP2011523888A JP2011523888A JP2012500271A5 JP 2012500271 A5 JP2012500271 A5 JP 2012500271A5 JP 2011523888 A JP2011523888 A JP 2011523888A JP 2011523888 A JP2011523888 A JP 2011523888A JP 2012500271 A5 JP2012500271 A5 JP 2012500271A5
- Authority
- JP
- Japan
- Prior art keywords
- lymphoma
- alkyl
- compound
- composition
- aralkyl
- 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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- 125000000217 alkyl group Chemical group 0.000 claims description 28
- 150000001875 compounds Chemical class 0.000 claims description 27
- 239000000203 mixture Substances 0.000 claims description 25
- 206010025323 Lymphomas Diseases 0.000 claims description 19
- 125000003118 aryl group Chemical group 0.000 claims description 14
- 208000017604 Hodgkin disease Diseases 0.000 claims description 13
- 208000021519 Hodgkin lymphoma Diseases 0.000 claims description 13
- 208000010747 Hodgkins lymphoma Diseases 0.000 claims description 13
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 229910052799 carbon Inorganic materials 0.000 claims description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
- 208000015914 Non-Hodgkin lymphomas Diseases 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- 208000027190 Peripheral T-cell lymphomas Diseases 0.000 claims description 8
- 208000031672 T-Cell Peripheral Lymphoma Diseases 0.000 claims description 8
- 208000020968 mature T-cell and NK-cell non-Hodgkin lymphoma Diseases 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 125000001072 heteroaryl group Chemical group 0.000 claims description 5
- 208000031671 Large B-Cell Diffuse Lymphoma Diseases 0.000 claims description 4
- 208000026911 Tuberous sclerosis complex Diseases 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 230000002354 daily effect Effects 0.000 claims description 4
- 206010012818 diffuse large B-cell lymphoma Diseases 0.000 claims description 4
- 230000003203 everyday effect Effects 0.000 claims description 4
- 125000000404 glutamine group Chemical group N[C@@H](CCC(N)=O)C(=O)* 0.000 claims description 4
- 125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 claims description 4
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 229910052711 selenium Inorganic materials 0.000 claims description 4
- 208000009999 tuberous sclerosis Diseases 0.000 claims description 4
- 208000036170 B-Cell Marginal Zone Lymphoma Diseases 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 238000000034 method Methods 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 10
- 239000007787 solid Substances 0.000 description 9
- 125000001424 substituent group Chemical group 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- JGDXFQORBMPJGR-YUMQZZPRSA-N (2S)-2-amino-5-[[(2R)-1-(carboxymethylamino)-3-(dimethylarsinothio)-1-oxopropan-2-yl]amino]-5-oxopentanoic acid Chemical compound OC(=O)CNC(=O)[C@H](CS[As](C)C)NC(=O)CC[C@H](N)C(O)=O JGDXFQORBMPJGR-YUMQZZPRSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 108700041071 darinaparsin Proteins 0.000 description 6
- OGGXGZAMXPVRFZ-UHFFFAOYSA-N dimethylarsinic acid Chemical compound C[As](C)(O)=O OGGXGZAMXPVRFZ-UHFFFAOYSA-N 0.000 description 6
- 239000012299 nitrogen atmosphere Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- DXCZGVVDXIPLCQ-UHFFFAOYSA-N chloro(dimethyl)arsane Chemical compound C[As](C)Cl DXCZGVVDXIPLCQ-UHFFFAOYSA-N 0.000 description 4
- 201000010099 disease Diseases 0.000 description 4
- RWSXRVCMGQZWBV-WDSKDSINSA-N glutathione Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O RWSXRVCMGQZWBV-WDSKDSINSA-N 0.000 description 4
- 208000015181 infectious disease Diseases 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 229950004243 cacodylic acid Drugs 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 150000002894 organic compounds Chemical class 0.000 description 3
- 230000002265 prevention Effects 0.000 description 3
- 208000024891 symptom Diseases 0.000 description 3
- 206010028980 Neoplasm Diseases 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- -1 aromatic organic compounds Chemical class 0.000 description 2
- 201000011510 cancer Diseases 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 230000012010 growth Effects 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 230000008058 pain sensation Effects 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 0 C*(C)SCC(C(NCC(O)=O)=O)NC(CCC(C(O)=O)N)=O Chemical compound C*(C)SCC(C(NCC(O)=O)=O)NC(CCC(C(O)=O)N)=O 0.000 description 1
- ZPCPDELXFCGLKX-UHFFFAOYSA-N C[As](O)(=O)C.C[As](Cl)C Chemical compound C[As](O)(=O)C.C[As](Cl)C ZPCPDELXFCGLKX-UHFFFAOYSA-N 0.000 description 1
- HJBWJAPEBGSQPR-UHFFFAOYSA-N DMCA Natural products COC1=CC=C(C=CC(O)=O)C=C1OC HJBWJAPEBGSQPR-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 108010024636 Glutathione Proteins 0.000 description 1
- 206010019280 Heart failures Diseases 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical group [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 150000001409 amidines Chemical group 0.000 description 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 150000001495 arsenic compounds Chemical class 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000000601 blood cell Anatomy 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 210000001185 bone marrow Anatomy 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 230000001934 delay Effects 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000002612 dispersion medium Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 229960003180 glutathione Drugs 0.000 description 1
- 201000005787 hematologic cancer Diseases 0.000 description 1
- 208000024200 hematopoietic and lymphoid system neoplasm Diseases 0.000 description 1
- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- VDEGQTCMQUFPFH-UHFFFAOYSA-N hydroxy-dimethyl-arsine Natural products C[As](C)O VDEGQTCMQUFPFH-UHFFFAOYSA-N 0.000 description 1
- 150000002466 imines Chemical group 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 210000001165 lymph node Anatomy 0.000 description 1
- 210000004698 lymphocyte Anatomy 0.000 description 1
- 201000007924 marginal zone B-cell lymphoma Diseases 0.000 description 1
- 208000021937 marginal zone lymphoma Diseases 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- AWIJRPNMLHPLNC-UHFFFAOYSA-N methanethioic s-acid Chemical compound SC=O AWIJRPNMLHPLNC-UHFFFAOYSA-N 0.000 description 1
- DYMRYCZRMAHYKE-UHFFFAOYSA-N n-diazonitramide Chemical group [O-][N+](=O)N=[N+]=[N-] DYMRYCZRMAHYKE-UHFFFAOYSA-N 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical group [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Chemical group 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical group [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical group [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 210000000952 spleen Anatomy 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical group 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical group [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- DUYAAUVXQSMXQP-UHFFFAOYSA-M thioacetate Chemical compound CC([S-])=O DUYAAUVXQSMXQP-UHFFFAOYSA-M 0.000 description 1
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US18951108P | 2008-08-20 | 2008-08-20 | |
| US61/189,511 | 2008-08-20 | ||
| PCT/US2009/053858 WO2010021928A1 (en) | 2008-08-20 | 2009-08-14 | Organoarsenic compounds and methods for the treatment of cancer |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014108079A Division JP5976036B2 (ja) | 2008-08-20 | 2014-05-26 | 有機ヒ素化合物および癌を処置するための方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2012500271A JP2012500271A (ja) | 2012-01-05 |
| JP2012500271A5 true JP2012500271A5 (enExample) | 2012-09-27 |
| JP5933896B2 JP5933896B2 (ja) | 2016-06-15 |
Family
ID=41707414
Family Applications (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011523888A Active JP5933896B2 (ja) | 2008-08-20 | 2009-08-14 | 有機ヒ素化合物および癌を処置するための方法 |
| JP2014108079A Active JP5976036B2 (ja) | 2008-08-20 | 2014-05-26 | 有機ヒ素化合物および癌を処置するための方法 |
| JP2015068284A Withdrawn JP2015120755A (ja) | 2008-08-20 | 2015-03-30 | 有機ヒ素化合物および癌を処置するための方法 |
| JP2016191062A Active JP6315841B2 (ja) | 2008-08-20 | 2016-09-29 | 有機ヒ素化合物および癌を処置するための方法 |
| JP2017242759A Pending JP2018039853A (ja) | 2008-08-20 | 2017-12-19 | 有機ヒ素化合物および癌を処置するための方法 |
Family Applications After (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014108079A Active JP5976036B2 (ja) | 2008-08-20 | 2014-05-26 | 有機ヒ素化合物および癌を処置するための方法 |
| JP2015068284A Withdrawn JP2015120755A (ja) | 2008-08-20 | 2015-03-30 | 有機ヒ素化合物および癌を処置するための方法 |
| JP2016191062A Active JP6315841B2 (ja) | 2008-08-20 | 2016-09-29 | 有機ヒ素化合物および癌を処置するための方法 |
| JP2017242759A Pending JP2018039853A (ja) | 2008-08-20 | 2017-12-19 | 有機ヒ素化合物および癌を処置するための方法 |
Country Status (19)
| Country | Link |
|---|---|
| US (4) | US20110269697A1 (enExample) |
| EP (2) | EP2321012B1 (enExample) |
| JP (5) | JP5933896B2 (enExample) |
| KR (3) | KR20170103023A (enExample) |
| CN (2) | CN104800828A (enExample) |
| AU (1) | AU2009282972A1 (enExample) |
| BR (1) | BRPI0918407A2 (enExample) |
| CA (1) | CA2734650A1 (enExample) |
| DK (2) | DK2321012T3 (enExample) |
| ES (2) | ES2703740T3 (enExample) |
| HK (1) | HK1212218A1 (enExample) |
| IL (1) | IL211153A0 (enExample) |
| MX (1) | MX2011001800A (enExample) |
| NZ (1) | NZ591181A (enExample) |
| PT (2) | PT3388111T (enExample) |
| RU (1) | RU2534606C2 (enExample) |
| SG (3) | SG10201810449XA (enExample) |
| WO (1) | WO2010021928A1 (enExample) |
| ZA (1) | ZA201101216B (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015085208A1 (en) * | 2013-12-05 | 2015-06-11 | Solasia Pharma K.K. | Compounds and methods for the treatment of cancer |
| CN104151397A (zh) * | 2014-07-03 | 2014-11-19 | 北京大学 | 一类新型三硫杂二环有机砷化物及其合成方法和在抗肿瘤领域里的应用 |
| JP6413969B2 (ja) * | 2015-07-29 | 2018-10-31 | 住友金属鉱山株式会社 | 日射遮蔽体形成用分散液および当該分散液を用いた日射遮蔽体 |
| JPWO2019220961A1 (ja) * | 2018-05-18 | 2020-05-28 | ソレイジア・ファーマ株式会社 | ダリナパルシンのアルカリ金属塩及び／又は無機酸付加塩の結晶型及びその製剤 |
| US11998654B2 (en) | 2018-07-12 | 2024-06-04 | Bard Shannon Limited | Securing implants and medical devices |
| CN113408945B (zh) * | 2021-07-15 | 2023-03-24 | 广西中烟工业有限责任公司 | 一种烤烟纯度的检测方法、装置、电子设备及存储介质 |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US234972A (en) | 1880-11-30 | William ennis | ||
| US761900A (en) | 1904-03-05 | 1904-06-07 | Newton Jefferson Norman | Flux compound. |
| US2349729A (en) | 1940-08-24 | 1944-05-23 | Parke Davis & Co | Therapeutic arsenic preparation |
| ATE493979T1 (de) | 1997-10-15 | 2011-01-15 | Polarx Biopharmaceuticals Inc | Zusammensetzungen und verfahren zur behandlung primärer und metastatischer erkrankungen mithilfe arsentrioxid |
| PT1964557E (pt) | 1997-11-10 | 2013-02-20 | Sloan Kettering Inst Cancer | Processo para a produção de formulações de trióxido de arsénio |
| CN1233476A (zh) | 1998-04-24 | 1999-11-03 | 陆道培 | 治疗急性白血病的药物及其制备方法 |
| EP1002537A1 (en) | 1998-10-30 | 2000-05-24 | Assistance Publique, Hopitaux De Paris | Use of melarsoprol for the manufacture of a medicament for treating B-cell lymphoproliferative diseases, such as multiple myeloma |
| US6191123B1 (en) | 1999-03-19 | 2001-02-20 | Parker Hughes Institute | Organic-arsenic compounds |
| CN1443064A (zh) | 2000-04-26 | 2003-09-17 | 俄勒冈健康科学大学 | 施用含硫醇化学保护化合物的方法 |
| DE10132625A1 (de) | 2001-07-05 | 2003-01-23 | Oce Printing Systems Gmbh | Verfahren, Computerprogrammprodukt und Gerätesystem zum visuellen Überprüfen von Bilddaten |
| WO2003057012A2 (en) * | 2002-01-07 | 2003-07-17 | Board Of Regents, The University Of Texas System | S-dimethylarsino-thiosuccinic acid s-dimethylarsino-2-thiobenzoic acid s-(dimethylarsino) glutathione as treatments for cancer |
| TW201350113A (zh) * | 2004-07-16 | 2013-12-16 | Texas A & M Univ Sys | 有機砷化合物、其用於治療癌症之用途及包含其之醫藥組成物 |
| ES2532666T3 (es) | 2005-07-29 | 2015-03-30 | Solasia Pharma K.K. | Compuestos y métodos para el tratamiento del cáncer |
| CN101395166B (zh) * | 2006-01-13 | 2014-07-09 | 得克萨斯州A&M大学系统 | 用于治疗癌症的化合物和方法 |
| TW200829261A (en) | 2006-09-29 | 2008-07-16 | Ziopharm Oncology Inc | Method for controlling angiogenesis in animals |
| CA2694987A1 (en) * | 2007-07-17 | 2009-01-22 | Combinatorx, Incorporated | Combinations for the treatment of b-cell proliferative disorders |
| US20090053168A1 (en) * | 2007-07-17 | 2009-02-26 | Richard Rickles | Treatments of b-cell proliferative disorders |
| KR20100100835A (ko) * | 2007-11-02 | 2010-09-15 | 지오팜 온콜로지 인코포레이티드 | 유기 비소제와의 병용 요법 |
| US20100009934A1 (en) * | 2008-06-09 | 2010-01-14 | Combinatorx, Incorporated | Beta adrenergic receptor agonists for the treatment of b-cell proliferative disorders |
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2009
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- 2009-08-14 KR KR1020117006250A patent/KR20110058818A/ko not_active Ceased
- 2009-08-14 PT PT09808635T patent/PT2321012T/pt unknown
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- 2009-08-14 JP JP2011523888A patent/JP5933896B2/ja active Active
- 2009-08-14 EP EP09808635.8A patent/EP2321012B1/en active Active
- 2009-08-14 BR BRPI0918407A patent/BRPI0918407A2/pt not_active Application Discontinuation
- 2009-08-14 AU AU2009282972A patent/AU2009282972A1/en not_active Abandoned
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- 2009-08-14 CN CN2009801356542A patent/CN102149432A/zh active Pending
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2017
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