CH510699A - Verfahren zur Herstellung von neuen Phosphorsäure- und Thiophosphorsäurederivaten - Google Patents
Verfahren zur Herstellung von neuen Phosphorsäure- und ThiophosphorsäurederivatenInfo
- Publication number
- CH510699A CH510699A CH967367A CH967367A CH510699A CH 510699 A CH510699 A CH 510699A CH 967367 A CH967367 A CH 967367A CH 967367 A CH967367 A CH 967367A CH 510699 A CH510699 A CH 510699A
- Authority
- CH
- Switzerland
- Prior art keywords
- group
- sep
- molecular weight
- low molecular
- hydrogen
- Prior art date
Links
- -1 thiophosphoric acid ester amides Chemical class 0.000 title claims abstract description 10
- 150000003014 phosphoric acid esters Chemical class 0.000 title abstract 2
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 17
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 15
- 125000005843 halogen group Chemical group 0.000 claims description 14
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 239000011230 binding agent Substances 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 239000012442 inert solvent Substances 0.000 claims description 4
- 150000003579 thiophosphoric acid derivatives Chemical class 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000005263 alkylenediamine group Chemical group 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 230000001419 dependent effect Effects 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 7
- 125000001188 haloalkyl group Chemical group 0.000 abstract description 2
- 229910052736 halogen Inorganic materials 0.000 abstract 3
- 150000002367 halogens Chemical class 0.000 abstract 3
- 239000000824 cytostatic agent Substances 0.000 abstract 1
- 231100000086 high toxicity Toxicity 0.000 abstract 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 27
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 26
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 17
- 229910052757 nitrogen Inorganic materials 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 8
- 239000000126 substance Substances 0.000 description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- GLZNEMWJNDMRFW-UHFFFAOYSA-N bis(2-chloroethyl)aminophosphonic acid dihydrochloride Chemical compound Cl.Cl.ClCCN(P(O)(=O)O)CCCl GLZNEMWJNDMRFW-UHFFFAOYSA-N 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 239000003610 charcoal Substances 0.000 description 4
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000012452 mother liquor Substances 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 238000009825 accumulation Methods 0.000 description 2
- 230000001665 lethal effect Effects 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 238000010899 nucleation Methods 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- UBRSKPGONDTDNE-UHFFFAOYSA-N 3-(2-chloroethylamino)propan-1-ol;hydrochloride Chemical compound Cl.OCCCNCCCl UBRSKPGONDTDNE-UHFFFAOYSA-N 0.000 description 1
- 206010003445 Ascites Diseases 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- GTXMEZUSXBSOME-UHFFFAOYSA-N CN(CCCl)P(O)(O)=O.Cl.Cl Chemical compound CN(CCCl)P(O)(O)=O.Cl.Cl GTXMEZUSXBSOME-UHFFFAOYSA-N 0.000 description 1
- 201000009030 Carcinoma Diseases 0.000 description 1
- 125000003580 L-valyl group Chemical group [H]N([H])[C@]([H])(C(=O)[*])C(C([H])([H])[H])(C([H])([H])[H])[H] 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- VZBYXSRVOPZTKL-UHFFFAOYSA-N OP(NCCCl)(O)=O.Cl.Cl Chemical compound OP(NCCCl)(O)=O.Cl.Cl VZBYXSRVOPZTKL-UHFFFAOYSA-N 0.000 description 1
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 1
- 206010039491 Sarcoma Diseases 0.000 description 1
- 208000001792 Sarcoma 37 Diseases 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 230000000973 chemotherapeutic effect Effects 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 230000001085 cytostatic effect Effects 0.000 description 1
- MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- ZISQKQRVRFMDOI-UHFFFAOYSA-N ethene propanamide Chemical compound N=C(CC)O.C=C ZISQKQRVRFMDOI-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 231100000518 lethal Toxicity 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- HAWPXGHAZFHHAD-UHFFFAOYSA-N mechlorethamine Chemical class ClCCN(C)CCCl HAWPXGHAZFHHAD-UHFFFAOYSA-N 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 150000003578 thiophosphoric acid amides Chemical class 0.000 description 1
- 238000002255 vaccination 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
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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1880070A CH512520A (de) | 1966-07-11 | 1967-07-07 | Verfahren zur Herstellung von neuen Phosphorsäure- und Thiophosphorsäurederivaten |
| CH1880170A CH509353A (de) | 1966-07-11 | 1967-07-07 | Verfahren zur Herstellung von neuen Phosphorsäure- und Thiophosphorsäurederivaten |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1966A0052989 DE1645921C3 (de) | 1966-07-11 | 1966-07-11 | 2-Oxo-13,2-osazaphosphorinane, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Präparate |
| US10656971A | 1971-01-14 | 1971-01-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH510699A true CH510699A (de) | 1971-07-31 |
Family
ID=25964360
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH967367A CH510699A (de) | 1966-07-11 | 1967-07-07 | Verfahren zur Herstellung von neuen Phosphorsäure- und Thiophosphorsäurederivaten |
Country Status (12)
| Country | Link |
|---|---|
| BE (1) | BE700711A (xx) |
| CH (1) | CH510699A (xx) |
| DE (1) | DE1645921C3 (xx) |
| DK (1) | DK119407B (xx) |
| ES (1) | ES342646A1 (xx) |
| FI (1) | FI48602C (xx) |
| FR (1) | FR6695M (xx) |
| GB (1) | GB1188159A (xx) |
| LU (1) | LU53924A1 (xx) |
| NL (1) | NL148323B (xx) |
| SE (1) | SE330174B (xx) |
| YU (2) | YU36187B (xx) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| 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 |
| DE3133077A1 (de) * | 1981-08-21 | 1983-03-10 | Henkel KGaA, 4000 Düsseldorf | Neue cytostatisch wirksame epoxidgruppen tragende 1,3,2-oxazaphosphorin-verbindungen, verfahren zu ihrer herstellung sowie ihre verwendung in pharmazeutischen zubereitungen |
| EP0235661A3 (de) * | 1986-02-22 | 1989-01-11 | ASTA Pharma Aktiengesellschaft | Neue heterocyclische Verbindungen mit einem 2-[2-(N,N-Bis-(2-chlorethyl)-diamido-phosphoryl-oxy)ethyl]-Rest |
| EP0281832B1 (de) * | 1987-03-06 | 1991-05-02 | ASTA Pharma Aktiengesellschaft | Verfahren zur Herstellung von Ifosfamid mit verbesserten Eigenschaften |
| GB9323399D0 (en) * | 1993-11-12 | 1994-01-05 | Univ Newcastle Ventures Ltd | Pharmaceutical formulations |
| DE19739159C1 (de) * | 1997-09-06 | 1999-01-28 | Asta Medica Ag | Verfahren zur Herstellung von Oxazaphosphorin-2-aminen |
-
1966
- 1966-07-11 DE DE1966A0052989 patent/DE1645921C3/de not_active Expired
-
1967
- 1967-06-20 LU LU53924D patent/LU53924A1/xx unknown
- 1967-06-30 BE BE700711D patent/BE700711A/xx not_active IP Right Cessation
- 1967-06-30 SE SE09970/67*A patent/SE330174B/xx unknown
- 1967-07-05 ES ES342646A patent/ES342646A1/es not_active Expired
- 1967-07-06 FI FI671879A patent/FI48602C/fi active
- 1967-07-07 CH CH967367A patent/CH510699A/de not_active IP Right Cessation
- 1967-07-10 DK DK353667AA patent/DK119407B/da not_active IP Right Cessation
- 1967-07-11 FR FR113841A patent/FR6695M/fr not_active Expired
- 1967-07-11 GB GB31849/67A patent/GB1188159A/en not_active Expired
- 1967-07-11 NL NL676709606A patent/NL148323B/xx not_active IP Right Cessation
-
1972
- 1972-12-28 YU YU03284/72A patent/YU36187B/xx unknown
-
1974
- 1974-08-16 YU YU2251/74A patent/YU39527B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR6695M (xx) | 1969-02-10 |
| SE330174B (xx) | 1970-11-09 |
| GB1188159A (en) | 1970-04-15 |
| FI48602C (fi) | 1974-11-11 |
| DE1645921C3 (de) | 1978-10-12 |
| YU39527B (en) | 1984-12-31 |
| LU53924A1 (xx) | 1967-08-21 |
| YU328472A (en) | 1981-06-30 |
| ES342646A1 (es) | 1968-10-16 |
| BE700711A (xx) | 1967-12-01 |
| FI48602B (xx) | 1974-07-31 |
| DE1645921B2 (de) | 1978-02-09 |
| DK119407B (da) | 1970-12-28 |
| DE1645921A1 (de) | 1970-07-16 |
| YU36187B (en) | 1982-02-25 |
| YU225174A (en) | 1982-02-28 |
| NL148323B (nl) | 1976-01-15 |
| NL6709606A (xx) | 1968-01-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |