SE452159B - Oxazafosforin-4-tio-alkansulfonsyror, deras neutrala salter, forfarande for framstellning derav samt farmaceutiska kompositioner innehallande dessa foreningar - Google Patents
Oxazafosforin-4-tio-alkansulfonsyror, deras neutrala salter, forfarande for framstellning derav samt farmaceutiska kompositioner innehallande dessa foreningarInfo
- Publication number
- SE452159B SE452159B SE8201807A SE8201807A SE452159B SE 452159 B SE452159 B SE 452159B SE 8201807 A SE8201807 A SE 8201807A SE 8201807 A SE8201807 A SE 8201807A SE 452159 B SE452159 B SE 452159B
- Authority
- SE
- Sweden
- Prior art keywords
- cation
- formula
- chloroethyl
- hydrogen
- oxazaphosphorin
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 51
- 150000003839 salts Chemical class 0.000 title claims description 17
- 238000000034 method Methods 0.000 title claims description 15
- 239000002253 acid Substances 0.000 title claims description 13
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- 239000008194 pharmaceutical composition Substances 0.000 title description 3
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- 150000001768 cations Chemical class 0.000 claims description 30
- 239000013543 active substance Substances 0.000 claims description 19
- 238000002360 preparation method Methods 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 239000002585 base Substances 0.000 claims description 14
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- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 8
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 159000000000 sodium salts Chemical class 0.000 claims description 7
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- 239000000969 carrier Substances 0.000 claims description 3
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- WOXAYWIFHYNRNI-UHFFFAOYSA-N n,n-bis(2-chloroethyl)-4-(2-oxidosulfonothioylethyl)-2-oxo-1,3,2$l^{5}-oxazaphosphinan-2-amine;cyclohexylazanium Chemical compound [NH3+]C1CCCCC1.[O-]S(=O)(=S)CCC1CCOP(=O)(N(CCCl)CCCl)N1 WOXAYWIFHYNRNI-UHFFFAOYSA-N 0.000 claims description 3
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- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 238000010837 poor prognosis Methods 0.000 description 1
- 230000002980 postoperative effect Effects 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 229930010796 primary metabolite Natural products 0.000 description 1
- 229960001404 quinidine Drugs 0.000 description 1
- 238000011470 radical surgery Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000012958 reprocessing Methods 0.000 description 1
- 201000006845 reticulosarcoma Diseases 0.000 description 1
- 208000029922 reticulum cell sarcoma Diseases 0.000 description 1
- 201000000306 sarcoidosis Diseases 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 239000004296 sodium metabisulphite Substances 0.000 description 1
- PUVLYVLUHVDBQG-UHFFFAOYSA-M sodium;3-[[2-[bis(2-chloroethyl)amino]-2-oxo-1,3,2$l^{5}-oxazaphosphinan-4-yl]sulfanyl]-2-methylpropane-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)CC(C)CSC1CCOP(=O)(N(CCCl)CCCl)N1 PUVLYVLUHVDBQG-UHFFFAOYSA-M 0.000 description 1
- VSOPDDIBJHHIBT-UHFFFAOYSA-M sodium;3-[[2-[bis(2-chloroethyl)amino]-2-oxo-1,3,2$l^{5}-oxazaphosphinan-4-yl]sulfanyl]propane-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)CCCSC1CCOP(=O)(N(CCCl)CCCl)N1 VSOPDDIBJHHIBT-UHFFFAOYSA-M 0.000 description 1
- JKAOVZCCVSYQKC-UHFFFAOYSA-M sodium;6-[[2-[bis(2-chloroethyl)amino]-2-oxo-1,3,2$l^{5}-oxazaphosphinan-4-yl]sulfanyl]hexane-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)CCCCCCSC1CCOP(=O)(N(CCCl)CCCl)N1 JKAOVZCCVSYQKC-UHFFFAOYSA-M 0.000 description 1
- PXRGAUOLIWDZSW-UHFFFAOYSA-M sodium;6-sulfanylhexane-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)CCCCCCS PXRGAUOLIWDZSW-UHFFFAOYSA-M 0.000 description 1
- 238000000527 sonication Methods 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 235000019337 sorbitan trioleate Nutrition 0.000 description 1
- 229960000391 sorbitan trioleate Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229960005453 strychnine Drugs 0.000 description 1
- 229960004793 sucrose Drugs 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 235000020238 sunflower seed Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000010497 wheat germ oil Substances 0.000 description 1
- 238000012982 x-ray structure analysis Methods 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
Classifications
-
- 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
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6581—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and nitrogen atoms with or without oxygen or sulfur atoms, as ring hetero atoms
- C07F9/6584—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and nitrogen atoms with or without oxygen or sulfur atoms, as ring hetero atoms having one phosphorus atom as ring hetero atom
- C07F9/65842—Cyclic amide derivatives of acids of phosphorus, in which one nitrogen atom belongs to the ring
- C07F9/65846—Cyclic amide derivatives of acids of phosphorus, in which one nitrogen atom belongs to the ring the phosphorus atom being part of a six-membered ring which may be condensed with another ring system
-
- 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)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19813111428 DE3111428A1 (de) | 1981-03-24 | 1981-03-24 | Oxazaphosphorin-4-thio-alkansulfonsaeuren und deren neutrale salze, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische zubereitungen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE8201807L SE8201807L (sv) | 1982-09-25 |
| SE452159B true SE452159B (sv) | 1987-11-16 |
Family
ID=6128090
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8201807A SE452159B (sv) | 1981-03-24 | 1982-03-22 | Oxazafosforin-4-tio-alkansulfonsyror, deras neutrala salter, forfarande for framstellning derav samt farmaceutiska kompositioner innehallande dessa foreningar |
Country Status (31)
| Country | Link |
|---|---|
| US (2) | US4623742A (da) |
| JP (1) | JPS57169496A (da) |
| AT (1) | AT381317B (da) |
| AU (1) | AU544493B2 (da) |
| BE (1) | BE892589A (da) |
| BG (1) | BG38489A3 (da) |
| CA (1) | CA1194479A (da) |
| CH (1) | CH648852A5 (da) |
| DD (1) | DD201799A5 (da) |
| DE (1) | DE3111428A1 (da) |
| DK (1) | DK171843B1 (da) |
| EG (1) | EG15703A (da) |
| ES (1) | ES8303440A1 (da) |
| FI (1) | FI69849C (da) |
| FR (1) | FR2502626B1 (da) |
| GB (1) | GB2095256B (da) |
| GR (1) | GR75533B (da) |
| HU (1) | HU186915B (da) |
| IE (1) | IE53054B1 (da) |
| IL (1) | IL65255A (da) |
| IT (1) | IT1150499B (da) |
| LU (1) | LU84032A1 (da) |
| NL (1) | NL192741C (da) |
| NO (1) | NO163692C (da) |
| PL (1) | PL129426B1 (da) |
| PT (1) | PT74641B (da) |
| RO (1) | RO84661B (da) |
| SE (1) | SE452159B (da) |
| SU (1) | SU1318167A3 (da) |
| YU (1) | YU61582A (da) |
| ZA (1) | ZA821637B (da) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3111428A1 (de) * | 1981-03-24 | 1982-10-07 | Asta-Werke Ag, Chemische Fabrik, 4800 Bielefeld | Oxazaphosphorin-4-thio-alkansulfonsaeuren und deren neutrale salze, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische zubereitungen |
| DE3279834D1 (en) * | 1981-12-31 | 1989-08-31 | Asta Pharma Ag | 4-sulfido-oxaza phosphorines and their use in the treatment of cancer, and in immunosuppression |
| ZA851062B (en) * | 1984-03-01 | 1985-11-27 | Asta Werke Ag Chem Fab | Salts of oxazaphosphorine derivatives and process for their production |
| DE3569737D1 (en) * | 1984-03-01 | 1989-06-01 | Asta Pharma Ag | Salts of oxazaphosphorine derivatives |
| DE3415726A1 (de) * | 1984-04-27 | 1985-10-31 | Asta-Werke Ag, Chemische Fabrik, 4800 Bielefeld | Verfahren zur herstellung von in 4-stellung substituierten oxazaphosphorin-derivaten |
| FR2567129B1 (fr) * | 1984-07-06 | 1986-12-05 | Adir | Nouveaux derives de l'oxaazaphosphorine, leur procede de preparation et les compositions pharmaceutiques les renfermant |
| US5204335A (en) * | 1986-10-31 | 1993-04-20 | Asta Pharma Aktiengesellschaft | Ifosfamide lyophilisate and process for its preparation |
| ES2040394T3 (es) * | 1988-03-19 | 1993-10-16 | Asta Medica Aktiengesellschaft | Procedimiento para preparar un material liofilizado de ifosfamida y mesna. |
| US5190929A (en) * | 1988-05-25 | 1993-03-02 | Research Corporation Technologies, Inc. | Cyclophosphamide analogs useful as anti-tumor agents |
| RO113611B1 (ro) * | 1990-08-03 | 1998-09-30 | Asta Pharma Ag | Preparate solide de ifosfamida, administrate oral si procedeu de obtinere |
| 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) |
| US20080223826A1 (en) * | 2007-03-13 | 2008-09-18 | Stephen Mazur | Reagent Delivery using a Membrane-Mediated Process |
| FR2968662B1 (fr) | 2010-12-10 | 2013-11-22 | Roussy Inst Gustave | Nouveaux derives d'oxazaphosphorines pre-activees, utilisation et methode de preparation |
| GB2626789A (en) * | 2023-02-03 | 2024-08-07 | Exactmer Ltd | Deprotection processes and cation scavengers for use in the same |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2107936C3 (de) * | 1971-02-19 | 1978-06-08 | Asta-Werke Ag Chemische Fabrik, 4800 Bielefeld | Alkylsulfonsäureester von 2-Oxo-13,2-oxazaphosphorinanen und diese enthaltende pharmazeutische Präparate |
| DE1645921C3 (de) * | 1966-07-11 | 1978-10-12 | Asta-Werke Ag Chemische Fabrik, 4800 Bielefeld | 2-Oxo-13,2-osazaphosphorinane, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Präparate |
| DE2201675A1 (de) * | 1972-01-14 | 1973-07-19 | Asta Werke Ag Chem Fab | Alkylsulfonsaeureester 1,3,2-oxazaphospha-cyclischer verbindungen, verfahren zu ihrer herstellung und pharmazeutische praeparate |
| JPS5159886A (da) * | 1974-11-20 | 1976-05-25 | Shionogi Seiyaku Kk | |
| JPS54157580A (en) | 1978-05-29 | 1979-12-12 | Otsuka Pharmaceut Co Ltd | Optically active oxazaphosphorine derivative |
| JPS5826919B2 (ja) | 1978-11-07 | 1983-06-06 | 大塚製薬株式会社 | シクロ↓−１，３，２↓−オキサアザホスホル誘導体の製造法 |
| JPS55154984A (en) * | 1979-05-24 | 1980-12-02 | Shionogi & Co Ltd | Novel 4-substituted-2h-1,3,2-oxaazaphospholine-2-oxide derivative |
| DE3220672A1 (de) | 1981-03-24 | 1983-12-08 | Asta-Werke Ag, Chemische Fabrik, 4800 Bielefeld | Cis-oxazaphosphorin-4-thio-alkansulfonsaeuren, ihre neutralen salze, verfahren zur herstellung derselben und diese enthaltenden pharmazeutischen praeparate |
| DE3111428A1 (de) | 1981-03-24 | 1982-10-07 | Asta-Werke Ag, Chemische Fabrik, 4800 Bielefeld | Oxazaphosphorin-4-thio-alkansulfonsaeuren und deren neutrale salze, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische zubereitungen |
| DE3220432A1 (de) | 1981-03-24 | 1983-12-01 | Asta-Werke Ag, Chemische Fabrik, 4800 Bielefeld | Oxazaphosphorin-4-thio-alkansulfonsaeure, ihre neutralen salze, verfahren zur herstellung derselben und diese enthaltenden pharmazeutischen praeparate |
-
1981
- 1981-03-24 DE DE19813111428 patent/DE3111428A1/de active Granted
-
1982
- 1982-03-08 CH CH1390/82A patent/CH648852A5/de not_active IP Right Cessation
- 1982-03-09 IE IE531/82A patent/IE53054B1/en unknown
- 1982-03-11 ZA ZA821637A patent/ZA821637B/xx unknown
- 1982-03-12 AU AU81344/82A patent/AU544493B2/en not_active Ceased
- 1982-03-12 GB GB8207375A patent/GB2095256B/en not_active Expired
- 1982-03-15 IL IL65255A patent/IL65255A/xx unknown
- 1982-03-17 AT AT0106382A patent/AT381317B/de not_active IP Right Cessation
- 1982-03-17 GR GR67621A patent/GR75533B/el unknown
- 1982-03-22 FR FR8204823A patent/FR2502626B1/fr not_active Expired
- 1982-03-22 RO RO106989A patent/RO84661B/ro unknown
- 1982-03-22 SE SE8201807A patent/SE452159B/sv not_active IP Right Cessation
- 1982-03-22 YU YU00615/82A patent/YU61582A/xx unknown
- 1982-03-23 CA CA000399098A patent/CA1194479A/en not_active Expired
- 1982-03-23 ES ES510677A patent/ES8303440A1/es not_active Expired
- 1982-03-23 SU SU823414100A patent/SU1318167A3/ru active
- 1982-03-23 IT IT20351/82A patent/IT1150499B/it active
- 1982-03-23 JP JP57044779A patent/JPS57169496A/ja active Granted
- 1982-03-23 PT PT74641A patent/PT74641B/pt unknown
- 1982-03-23 NO NO820957A patent/NO163692C/no not_active IP Right Cessation
- 1982-03-23 DD DD82238374A patent/DD201799A5/de unknown
- 1982-03-23 EG EG82156A patent/EG15703A/xx active
- 1982-03-23 HU HU82879A patent/HU186915B/hu unknown
- 1982-03-23 BE BE2/59642A patent/BE892589A/fr not_active IP Right Cessation
- 1982-03-23 FI FI821021A patent/FI69849C/fi not_active IP Right Cessation
- 1982-03-23 DK DK129882A patent/DK171843B1/da not_active IP Right Cessation
- 1982-03-24 NL NL8201227A patent/NL192741C/nl not_active IP Right Cessation
- 1982-03-24 LU LU84032A patent/LU84032A1/de unknown
- 1982-03-24 BG BG055941A patent/BG38489A3/xx unknown
- 1982-08-24 PL PL1982235606A patent/PL129426B1/pl unknown
-
1984
- 1984-12-19 US US06/683,374 patent/US4623742A/en not_active Expired - Lifetime
-
1988
- 1988-02-02 US US07/149,954 patent/US4929607A/en not_active Expired - Lifetime
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