CA2580802C - Medicinal disulfide salts - Google Patents
Medicinal disulfide salts Download PDFInfo
- Publication number
- CA2580802C CA2580802C CA2580802A CA2580802A CA2580802C CA 2580802 C CA2580802 C CA 2580802C CA 2580802 A CA2580802 A CA 2580802A CA 2580802 A CA2580802 A CA 2580802A CA 2580802 C CA2580802 C CA 2580802C
- Authority
- CA
- Canada
- Prior art keywords
- group
- compound
- formula
- ion
- alkylene
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 150000002019 disulfides Chemical class 0.000 title abstract description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 35
- 150000003839 salts Chemical class 0.000 claims abstract description 20
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 11
- 229910052711 selenium Inorganic materials 0.000 claims description 11
- 239000011669 selenium Substances 0.000 claims description 11
- -1 selenium ion Chemical class 0.000 claims description 10
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 9
- 150000008575 L-amino acids Chemical group 0.000 claims description 9
- 125000002947 alkylene group Chemical group 0.000 claims description 9
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 8
- 150000002500 ions Chemical class 0.000 claims description 8
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical group NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 229910021645 metal ion Inorganic materials 0.000 claims description 7
- 229910052717 sulfur Chemical group 0.000 claims description 7
- 239000011593 sulfur Chemical group 0.000 claims description 7
- 229930064664 L-arginine Natural products 0.000 claims description 6
- 235000014852 L-arginine Nutrition 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052737 gold Inorganic materials 0.000 claims description 6
- 239000010931 gold Substances 0.000 claims description 6
- 229910052709 silver Inorganic materials 0.000 claims description 6
- 239000004332 silver Substances 0.000 claims description 6
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 5
- 229930195714 L-glutamate Chemical group 0.000 claims description 5
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical group OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 229910052791 calcium Inorganic materials 0.000 claims description 5
- 239000011575 calcium Substances 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 235000019766 L-Lysine Nutrition 0.000 claims description 4
- 239000004472 Lysine Chemical group 0.000 claims description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 4
- 229910052749 magnesium Inorganic materials 0.000 claims description 4
- 239000011777 magnesium Substances 0.000 claims description 4
- 229910052712 strontium Inorganic materials 0.000 claims description 4
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 claims description 4
- 125000002059 L-arginyl group Chemical group O=C([*])[C@](N([H])[H])([H])C([H])([H])C([H])([H])C([H])([H])N([H])C(=N[H])N([H])[H] 0.000 claims 1
- 125000001176 L-lysyl group Chemical group [H]N([H])[C@]([H])(C(=O)[*])C([H])([H])C([H])([H])C([H])([H])C(N([H])[H])([H])[H] 0.000 claims 1
- 231100000419 toxicity Toxicity 0.000 abstract description 7
- 230000001988 toxicity Effects 0.000 abstract description 7
- 239000002246 antineoplastic agent Substances 0.000 abstract description 3
- 239000003638 chemical reducing agent Substances 0.000 abstract description 3
- 229940034982 antineoplastic agent Drugs 0.000 abstract description 2
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 abstract description 2
- KQYGMURBTJPBPQ-UHFFFAOYSA-L disodium;2-(2-sulfonatoethyldisulfanyl)ethanesulfonate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)CCSSCCS([O-])(=O)=O KQYGMURBTJPBPQ-UHFFFAOYSA-L 0.000 description 17
- 239000000047 product Substances 0.000 description 17
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- 229950009278 dimesna Drugs 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 12
- 235000002639 sodium chloride Nutrition 0.000 description 12
- 101150041968 CDC13 gene Proteins 0.000 description 10
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- XOGTZOOQQBDUSI-UHFFFAOYSA-M Mesna Chemical compound [Na+].[O-]S(=O)(=O)CCS XOGTZOOQQBDUSI-UHFFFAOYSA-M 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 5
- BYUKOOOZTSTOOH-UHFFFAOYSA-N 2-(2-sulfoethyldisulfanyl)ethanesulfonic acid Chemical compound OS(=O)(=O)CCSSCCS(O)(=O)=O BYUKOOOZTSTOOH-UHFFFAOYSA-N 0.000 description 5
- ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical compound OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 description 5
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 229910052697 platinum Inorganic materials 0.000 description 3
- WPLOVIFNBMNBPD-ATHMIXSHSA-N subtilin Chemical compound CC1SCC(NC2=O)C(=O)NC(CC(N)=O)C(=O)NC(C(=O)NC(CCCCN)C(=O)NC(C(C)CC)C(=O)NC(=C)C(=O)NC(CCCCN)C(O)=O)CSC(C)C2NC(=O)C(CC(C)C)NC(=O)C1NC(=O)C(CCC(N)=O)NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C1NC(=O)C(=C/C)/NC(=O)C(CCC(N)=O)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)CNC(=O)C(NC(=O)C(NC(=O)C2NC(=O)CNC(=O)C3CCCN3C(=O)C(NC(=O)C3NC(=O)C(CC(C)C)NC(=O)C(=C)NC(=O)C(CCC(O)=O)NC(=O)C(NC(=O)C(CCCCN)NC(=O)C(N)CC=4C5=CC=CC=C5NC=4)CSC3)C(C)SC2)C(C)C)C(C)SC1)CC1=CC=CC=C1 WPLOVIFNBMNBPD-ATHMIXSHSA-N 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- SBVBTACBXIOUDD-UHFFFAOYSA-N 2-(2-chlorosulfonylethyldisulfanyl)ethanesulfonyl chloride Chemical compound ClS(=O)(=O)CCSSCCS(Cl)(=O)=O SBVBTACBXIOUDD-UHFFFAOYSA-N 0.000 description 2
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- 206010027439 Metal poisoning Diseases 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 2
- 239000000920 calcium hydroxide Substances 0.000 description 2
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 description 2
- 229960004316 cisplatin Drugs 0.000 description 2
- 208000010501 heavy metal poisoning Diseases 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 229960003552 other antineoplastic agent in atc Drugs 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 208000007056 sickle cell anemia Diseases 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- ZTSMMXZXMYYIHF-MDTVQASCSA-N (2s)-2,6-diaminohexanoic acid;2-(2-sulfoethyldisulfanyl)ethanesulfonic acid Chemical compound NCCCC[C@H](N)C(O)=O.NCCCC[C@H](N)C(O)=O.OS(=O)(=O)CCSSCCS(O)(=O)=O ZTSMMXZXMYYIHF-MDTVQASCSA-N 0.000 description 1
- CRONFVSERHYUQT-SCGRZTRASA-N (2s)-2-amino-5-(diaminomethylideneamino)pentanoic acid;2-(2-sulfoethyldisulfanyl)ethanesulfonic acid Chemical compound OC(=O)[C@@H](N)CCCNC(N)=N.OC(=O)[C@@H](N)CCCNC(N)=N.OS(=O)(=O)CCSSCCS(O)(=O)=O CRONFVSERHYUQT-SCGRZTRASA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 description 1
- 206010073306 Exposure to radiation Diseases 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 206010029155 Nephropathy toxic Diseases 0.000 description 1
- 206010029350 Neurotoxicity Diseases 0.000 description 1
- 206010067482 No adverse event Diseases 0.000 description 1
- 229930012538 Paclitaxel Natural products 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical group OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- 229910006069 SO3H Inorganic materials 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 229940123237 Taxane Drugs 0.000 description 1
- 206010044221 Toxic encephalopathy Diseases 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000001335 aliphatic alkanes Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 239000002295 alkylating antineoplastic agent Substances 0.000 description 1
- 239000000729 antidote Substances 0.000 description 1
- 229940075522 antidotes Drugs 0.000 description 1
- 229940041181 antineoplastic drug Drugs 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- PBAYDYUZOSNJGU-UHFFFAOYSA-N chelidonic acid Natural products OC(=O)C1=CC(=O)C=C(C(O)=O)O1 PBAYDYUZOSNJGU-UHFFFAOYSA-N 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 229960004397 cyclophosphamide Drugs 0.000 description 1
- DHAWZTQUNPRNOO-UHFFFAOYSA-N diazanium;2-(2-sulfonatoethyldisulfanyl)ethanesulfonate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)CCSSCCS([O-])(=O)=O DHAWZTQUNPRNOO-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 125000004119 disulfanediyl group Chemical class *SS* 0.000 description 1
- 125000002228 disulfide group Chemical group 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 231100000755 favorable toxicity profile Toxicity 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229960001101 ifosfamide Drugs 0.000 description 1
- HOMGKSMUEGBAAB-UHFFFAOYSA-N ifosfamide Chemical compound ClCCNP1(=O)OCCCN1CCCl HOMGKSMUEGBAAB-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000006193 liquid solution Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 229960004635 mesna Drugs 0.000 description 1
- 229940101533 mesnex Drugs 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 230000007694 nephrotoxicity Effects 0.000 description 1
- 231100000417 nephrotoxicity Toxicity 0.000 description 1
- 230000007135 neurotoxicity Effects 0.000 description 1
- 231100000228 neurotoxicity Toxicity 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229960001592 paclitaxel Drugs 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 238000009520 phase I clinical trial Methods 0.000 description 1
- 238000009522 phase III clinical trial Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000003223 protective agent Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- DKPFODGZWDEEBT-QFIAKTPHSA-N taxane Chemical class C([C@]1(C)CCC[C@@H](C)[C@H]1C1)C[C@H]2[C@H](C)CC[C@@H]1C2(C)C DKPFODGZWDEEBT-QFIAKTPHSA-N 0.000 description 1
- RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/64—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and sulfur atoms, not being part of thio groups, bound to the same carbon skeleton
- C07C323/66—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and sulfur atoms, not being part of thio groups, bound to the same carbon skeleton containing sulfur atoms of sulfo, esterified sulfo or halosulfonyl groups, bound to the carbon skeleton
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/02—Antidotes
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/06—Free radical scavengers or antioxidants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Toxicology (AREA)
- Biochemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/945,809 US7282602B2 (en) | 2004-09-21 | 2004-09-21 | Medicinal disulfide salts |
| US10/945,809 | 2004-09-21 | ||
| PCT/US2005/033774 WO2006034327A1 (en) | 2004-09-21 | 2005-09-21 | Medicinal disulfide salts |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2580802A1 CA2580802A1 (en) | 2006-03-30 |
| CA2580802C true CA2580802C (en) | 2012-11-20 |
Family
ID=36074969
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2580802A Expired - Fee Related CA2580802C (en) | 2004-09-21 | 2005-09-21 | Medicinal disulfide salts |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US7282602B2 (enExample) |
| EP (1) | EP1797031A4 (enExample) |
| JP (1) | JP5015781B2 (enExample) |
| CN (1) | CN101076513A (enExample) |
| CA (1) | CA2580802C (enExample) |
| MX (1) | MX2007003174A (enExample) |
| WO (1) | WO2006034327A1 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011067653A1 (en) * | 2009-12-04 | 2011-06-09 | Carlo Ghisalberti | Oral compositions for use in the mercury intoxication from dental amalgam |
| JP6271233B2 (ja) * | 2013-11-29 | 2018-01-31 | ローム・アンド・ハース電子材料株式会社 | 表面処理液 |
| WO2015106240A1 (en) | 2014-01-13 | 2015-07-16 | The General Hospital Corporation | Heteroaryl disulfide compounds as allosteric effectors for increasing the oxygen-binding affinity of hemoglobin |
| JP2023509985A (ja) * | 2020-01-10 | 2023-03-10 | ランタン ファルマ インコーポレイテッド | ２，２’－ジチオ－ビス－エタンスルホン酸塩に対する感受性を決定する方法 |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE593047A (enExample) * | 1959-07-17 | |||
| DE2025538A1 (de) * | 1970-04-02 | 1971-10-21 | Lokomotivbau Elektrotech | Verfahren zur galvanischen Glanzverkupferung aus sauren Elektrolyten |
| BE788685A (nl) * | 1971-09-13 | 1973-03-12 | Agfa Gevaert Nv | Ontwikkeling van contrastrijke zilverhalogenide-emulsies voor grafischedoeleinden |
| DD122086A1 (enExample) * | 1975-06-16 | 1976-09-12 | ||
| IT1185551B (it) * | 1985-04-15 | 1987-11-12 | Schering Spa | Composizioni farmaceutiche a base di acido mercaptoetansolfonico ad attivita' terapeutica,derivati salini organici dell'acido mercaptoetansolfonico utili per tali composizioni e relativo procedimento di preparazione |
| DE4032864A1 (de) * | 1990-10-13 | 1992-04-16 | Schering Ag | Saures bad zur galvanischen abscheidung von kupferueberzuegen und verfahren unter verwendung dieser kombination |
| DE4127821A1 (de) * | 1991-08-23 | 1993-02-25 | Basf Ag | Disulfide, verfahren zu deren herstellung und deren verwendung |
| US5789000A (en) * | 1994-11-14 | 1998-08-04 | Bionumerik Pharmaceuticals, Inc. | Sterile aqueous parenteral formulations of cis-diammine dichloro platinum |
| US5661188A (en) * | 1995-06-07 | 1997-08-26 | Medical Research Foundation and Infrastructure Development for Health Services--Nahariya Hospital Branch | Therapeutic uses for sodium 2-mercaptoethanesulphonate (mesna) |
| CA2263166C (en) * | 1996-09-23 | 2006-12-12 | Bionumerik Pharmaceuticals, Inc. | Reducing toxic effects of carboplatin using dithioethers |
| ES2163197T3 (es) * | 1996-10-01 | 2002-01-16 | Bionumerik Pharmaceuticals Inc | Procedimiento para producir ditiobis-alcanosulfonatos y fosfonatos. |
| US6160167A (en) * | 1998-04-21 | 2000-12-12 | Bionumerik Pharmaceuticals, Inc. | Mercaptans and disulfides |
| JP3124523B2 (ja) * | 1999-01-28 | 2001-01-15 | 日本エレクトロプレイテイング・エンジニヤース株式会社 | 銅メッキ方法 |
| KR20020029626A (ko) * | 2000-10-13 | 2002-04-19 | 마티네즈 길러모 | 전해질 |
| JP2003072231A (ja) * | 2001-09-06 | 2003-03-12 | Oji Paper Co Ltd | インクジェット記録用シート |
| US6504049B1 (en) * | 2002-04-30 | 2003-01-07 | Bionumerik Pharmaceuticals, Inc. | Process for synthesizing pharmaceutically active disulfide salts |
| KR100598994B1 (ko) * | 2002-12-25 | 2006-07-07 | 닛코킨조쿠 가부시키가이샤 | 특정골격을 갖는 4급아민화합물 중합체 및 유기유황화합물을 첨가제로서 포함하는 동전해액 및 그것에 의하여 제조되는 전해동박 |
| JP2005048256A (ja) * | 2003-07-30 | 2005-02-24 | Asahi Denka Kogyo Kk | 銅メッキ用添加剤、銅メッキ浴および銅メッキ方法 |
| JP2006104134A (ja) * | 2004-10-06 | 2006-04-20 | Asahi Denka Kogyo Kk | ジスルフィド類の製造方法 |
| JP4750486B2 (ja) * | 2005-07-06 | 2011-08-17 | 株式会社Adeka | 電解銅メッキ用添加剤、該添加剤を含有する電解銅メッキ浴及び該メッキ浴を使用する電解銅メッキ方法 |
-
2004
- 2004-09-21 US US10/945,809 patent/US7282602B2/en not_active Expired - Lifetime
-
2005
- 2005-09-21 JP JP2007532635A patent/JP5015781B2/ja not_active Expired - Lifetime
- 2005-09-21 WO PCT/US2005/033774 patent/WO2006034327A1/en not_active Ceased
- 2005-09-21 EP EP05801177A patent/EP1797031A4/en not_active Withdrawn
- 2005-09-21 CN CNA200580035465XA patent/CN101076513A/zh active Pending
- 2005-09-21 MX MX2007003174A patent/MX2007003174A/es active IP Right Grant
- 2005-09-21 CA CA2580802A patent/CA2580802C/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| MX2007003174A (es) | 2008-01-11 |
| US20060063949A1 (en) | 2006-03-23 |
| EP1797031A1 (en) | 2007-06-20 |
| US7282602B2 (en) | 2007-10-16 |
| CA2580802A1 (en) | 2006-03-30 |
| WO2006034327A1 (en) | 2006-03-30 |
| JP2008513503A (ja) | 2008-05-01 |
| EP1797031A4 (en) | 2009-12-16 |
| JP5015781B2 (ja) | 2012-08-29 |
| CN101076513A (zh) | 2007-11-21 |
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