MXPA04010859A - Procedimiento para sintetizar sales de disulfuros farmaceuticamente activas. - Google Patents
Procedimiento para sintetizar sales de disulfuros farmaceuticamente activas.Info
- Publication number
- MXPA04010859A MXPA04010859A MXPA04010859A MXPA04010859A MXPA04010859A MX PA04010859 A MXPA04010859 A MX PA04010859A MX PA04010859 A MXPA04010859 A MX PA04010859A MX PA04010859 A MXPA04010859 A MX PA04010859A MX PA04010859 A MXPA04010859 A MX PA04010859A
- Authority
- MX
- Mexico
- Prior art keywords
- compound
- lower alkyl
- dimesna
- formula
- synthesizing
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 38
- 230000002194 synthesizing effect Effects 0.000 title claims abstract description 9
- 150000002019 disulfides Chemical class 0.000 title abstract description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 13
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 7
- 239000001301 oxygen Substances 0.000 claims abstract description 7
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract description 6
- -1 alkali metal salt Chemical class 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 239000007858 starting material Substances 0.000 claims description 9
- 239000002585 base Substances 0.000 claims description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 239000013067 intermediate product Substances 0.000 claims description 2
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims description 2
- KOUKXHPPRFNWPP-UHFFFAOYSA-N pyrazine-2,5-dicarboxylic acid;hydrate Chemical compound O.OC(=O)C1=CN=C(C(O)=O)C=N1 KOUKXHPPRFNWPP-UHFFFAOYSA-N 0.000 claims description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical group O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 1
- 229910001882 dioxygen Inorganic materials 0.000 claims 1
- 238000005987 sulfurization reaction Methods 0.000 claims 1
- 229950009278 dimesna Drugs 0.000 abstract description 17
- 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 abstract description 14
- 125000002947 alkylene group Chemical group 0.000 abstract description 2
- 230000003113 alkalizing effect Effects 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 229960004635 mesna Drugs 0.000 description 12
- 239000000047 product Substances 0.000 description 11
- XOGTZOOQQBDUSI-UHFFFAOYSA-M Mesna Chemical compound [Na+].[O-]S(=O)(=O)CCS XOGTZOOQQBDUSI-UHFFFAOYSA-M 0.000 description 6
- 239000003223 protective agent Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 4
- 239000002246 antineoplastic agent Substances 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- 229940041181 antineoplastic drug Drugs 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 239000011630 iodine Substances 0.000 description 3
- 239000007800 oxidant agent Substances 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- DUYAAUVXQSMXQP-UHFFFAOYSA-M thioacetate Chemical compound CC([S-])=O DUYAAUVXQSMXQP-UHFFFAOYSA-M 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- JYWKEVKEKOTYEX-UHFFFAOYSA-N 2,6-dibromo-4-chloroiminocyclohexa-2,5-dien-1-one Chemical compound ClN=C1C=C(Br)C(=O)C(Br)=C1 JYWKEVKEKOTYEX-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000003057 platinum Chemical class 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 description 2
- KODOIOCJZCCYHX-UHFFFAOYSA-N 2-acetylsulfanylethanesulfonic acid Chemical compound CC(=O)SCCS(O)(=O)=O KODOIOCJZCCYHX-UHFFFAOYSA-N 0.000 description 1
- 206010065553 Bone marrow failure Diseases 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical class SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
- 206010029350 Neurotoxicity Diseases 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 206010044221 Toxic encephalopathy Diseases 0.000 description 1
- FDHVBYBVKBOBEA-UHFFFAOYSA-L [Na+].[Na+].[O-]P(=O)OCBr.[O-]P(=O)OCBr Chemical compound [Na+].[Na+].[O-]P(=O)OCBr.[O-]P(=O)OCBr FDHVBYBVKBOBEA-UHFFFAOYSA-L 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- VSRXQHXAPYXROS-UHFFFAOYSA-N azanide;cyclobutane-1,1-dicarboxylic acid;platinum(2+) Chemical compound [NH2-].[NH2-].[Pt+2].OC(=O)C1(C(O)=O)CCC1 VSRXQHXAPYXROS-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 229960004562 carboplatin Drugs 0.000 description 1
- 229940044683 chemotherapy drug Drugs 0.000 description 1
- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 description 1
- 229960004316 cisplatin Drugs 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 229940127089 cytotoxic agent Drugs 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 230000007135 neurotoxicity Effects 0.000 description 1
- 231100000228 neurotoxicity Toxicity 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C327/00—Thiocarboxylic acids
- C07C327/20—Esters of monothiocarboxylic acids
- C07C327/22—Esters of monothiocarboxylic acids having carbon atoms of esterified thiocarboxyl groups bound to hydrogen atoms or to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/22—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of hydropolysulfides or polysulfides
- C07C319/24—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of hydropolysulfides or polysulfides by reactions involving the formation of sulfur-to-sulfur bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
- C07F9/3808—Acyclic saturated acids which can have further substituents on alkyl
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/135,756 US6504049B1 (en) | 2002-04-30 | 2002-04-30 | Process for synthesizing pharmaceutically active disulfide salts |
| PCT/US2003/013178 WO2003093226A1 (en) | 2002-04-30 | 2003-04-29 | Process for synthesizing pharmaceutically active disulfide salts |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MXPA04010859A true MXPA04010859A (es) | 2005-02-14 |
Family
ID=22469512
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MXPA04010859A MXPA04010859A (es) | 2002-04-30 | 2003-04-29 | Procedimiento para sintetizar sales de disulfuros farmaceuticamente activas. |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US6504049B1 (enExample) |
| EP (1) | EP1499587B1 (enExample) |
| JP (1) | JP4478561B2 (enExample) |
| AU (1) | AU2003231169B2 (enExample) |
| CA (1) | CA2483775C (enExample) |
| DK (1) | DK1499587T3 (enExample) |
| ES (1) | ES2523653T3 (enExample) |
| MX (1) | MXPA04010859A (enExample) |
| PT (1) | PT1499587E (enExample) |
| WO (1) | WO2003093226A1 (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2811987A1 (fr) * | 2000-07-18 | 2002-01-25 | Expansia Sa | Procede de preparation du 2,2'-dithiobis(ethanesulfonate) de disodium |
| US8710095B2 (en) | 2002-04-30 | 2014-04-29 | Bionumerik Pharmaceuticals, Inc. | Drugs for prophylaxis or mitigation of taxane-induced neurotoxicity |
| US7317124B2 (en) | 2003-11-13 | 2008-01-08 | Sanofi-Aventis Deutschland Gmbh | Ortho-substituted pentafluorosulfanylbenzenes, process for their preparation and their use as valuable synthetic intermediates |
| AU2004299131B2 (en) * | 2003-12-17 | 2010-05-13 | Bionumerik Pharmaceuticals, Inc. | Process for synthesizing disulfides |
| US7282602B2 (en) * | 2004-09-21 | 2007-10-16 | Bionumerik Pharmaceuticals, Inc. | Medicinal disulfide salts |
| EP2004175A4 (en) * | 2006-03-16 | 2010-12-15 | Bionumerik Pharmaceuticals Inc | COMPOUNDS AND FORMULATIONS FOR INCREASING THE EFFECT OF CANCER AND METHOD FOR THEIR USE |
| JP5109081B2 (ja) * | 2006-04-26 | 2012-12-26 | 東洋紡株式会社 | アルケンスルホン酸塩を用いたチオカルボアルキルアルカンスルホン酸塩、メルカプトアルカンスルホン酸塩およびジチオビス（アルカンスルホン酸）塩の製造方法 |
| CN101917976B (zh) * | 2007-11-20 | 2013-08-28 | 兰肯瑙医学研究所 | 二硫化物化疗药及其在制备癌症治疗的药物中的应用 |
| DK2249825T3 (en) | 2008-03-14 | 2016-01-11 | Bionumerik Pharmaceuticals Inc | Treatment methods and compositions for lung cancer, adenocarcinoma, and other medical conditions |
| WO2009113989A1 (en) | 2008-03-14 | 2009-09-17 | Bionumerik Pharmaceuticals, Inc. | Compositions and methods of use of compounds to increase cancer patient survival time |
| EP2430178B1 (en) | 2009-05-15 | 2014-07-09 | Lankenau Institute for Medical Research | Methods and kits for measuring toxicity and oxidative stress in live cells |
| CN108914171B (zh) * | 2018-07-19 | 2020-05-19 | 广东工业大学 | 一种加速铜沉积添加剂及其制备方法和应用 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2396879A (en) * | 1945-04-12 | 1946-03-19 | Eastman Kodak Co | Sulphur-containing esters |
| CS252564B1 (cs) * | 1985-06-17 | 1987-09-17 | Jiri Jary | Způsob výroby 2-merkaptoethansulfonové kyseliny |
| EP0934261B1 (en) * | 1996-10-01 | 2001-10-31 | Bionumerik Pharmaceuticals, Inc. | Process for producing dithiobis-alkanesulfonates and phosphonates |
| FR2811987A1 (fr) * | 2000-07-18 | 2002-01-25 | Expansia Sa | Procede de preparation du 2,2'-dithiobis(ethanesulfonate) de disodium |
-
2002
- 2002-04-30 US US10/135,756 patent/US6504049B1/en not_active Expired - Lifetime
-
2003
- 2003-04-29 CA CA2483775A patent/CA2483775C/en not_active Expired - Fee Related
- 2003-04-29 MX MXPA04010859A patent/MXPA04010859A/es active IP Right Grant
- 2003-04-29 PT PT37243011T patent/PT1499587E/pt unknown
- 2003-04-29 WO PCT/US2003/013178 patent/WO2003093226A1/en not_active Ceased
- 2003-04-29 AU AU2003231169A patent/AU2003231169B2/en not_active Ceased
- 2003-04-29 ES ES03724301.1T patent/ES2523653T3/es not_active Expired - Lifetime
- 2003-04-29 DK DK03724301.1T patent/DK1499587T3/en active
- 2003-04-29 EP EP03724301.1A patent/EP1499587B1/en not_active Expired - Lifetime
- 2003-04-29 JP JP2004501366A patent/JP4478561B2/ja not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| EP1499587A1 (en) | 2005-01-26 |
| JP2005523935A (ja) | 2005-08-11 |
| EP1499587A4 (en) | 2006-05-24 |
| AU2003231169B2 (en) | 2008-09-04 |
| EP1499587B1 (en) | 2014-11-05 |
| AU2003231169A1 (en) | 2003-11-17 |
| ES2523653T3 (es) | 2014-11-28 |
| WO2003093226A1 (en) | 2003-11-13 |
| US6504049B1 (en) | 2003-01-07 |
| DK1499587T3 (en) | 2015-01-26 |
| CA2483775C (en) | 2011-02-08 |
| PT1499587E (pt) | 2014-11-21 |
| JP4478561B2 (ja) | 2010-06-09 |
| CA2483775A1 (en) | 2003-11-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FG | Grant or registration |