DE2552135A1 - 4-hydroperoxy-tetrahydro-2h- 1,3,2-oxazaphosphorin-2-oxid-derivate - Google Patents
4-hydroperoxy-tetrahydro-2h- 1,3,2-oxazaphosphorin-2-oxid-derivateInfo
- Publication number
- DE2552135A1 DE2552135A1 DE19752552135 DE2552135A DE2552135A1 DE 2552135 A1 DE2552135 A1 DE 2552135A1 DE 19752552135 DE19752552135 DE 19752552135 DE 2552135 A DE2552135 A DE 2552135A DE 2552135 A1 DE2552135 A1 DE 2552135A1
- Authority
- DE
- Germany
- Prior art keywords
- oxazaphosphorine
- tetrahydro
- hydroperoxy
- methyl
- oxide
- 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.)
- Withdrawn
Links
- LUNCDJWGERPUOC-UHFFFAOYSA-N OOC1CCOP(=O)N1 Chemical class OOC1CCOP(=O)N1 LUNCDJWGERPUOC-UHFFFAOYSA-N 0.000 title 1
- -1 2-methanesulfonyloxyethyl Chemical group 0.000 claims description 28
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 12
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 10
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 claims description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 8
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 239000011541 reaction mixture Substances 0.000 claims description 5
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 229940079593 drug Drugs 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 3
- 150000002978 peroxides Chemical class 0.000 claims description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims description 2
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 claims description 2
- 229960003750 ethyl chloride Drugs 0.000 claims description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000003208 petroleum Substances 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims 1
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 claims 1
- 229960001701 chloroform Drugs 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 239000000460 chlorine Substances 0.000 description 6
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 6
- CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 description 5
- 229960004397 cyclophosphamide Drugs 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- JURKWYPVKGLSBL-UHFFFAOYSA-N 4-diaminophosphoryloxybut-1-ene Chemical compound NP(N)(=O)OCCC=C JURKWYPVKGLSBL-UHFFFAOYSA-N 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 4
- 206010028980 Neoplasm Diseases 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 210000004881 tumor cell Anatomy 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 3
- 229940125890 compound Ia Drugs 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- 241001494479 Pecora Species 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000002026 chloroform extract Substances 0.000 description 2
- 210000003743 erythrocyte Anatomy 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 230000001506 immunosuppresive effect Effects 0.000 description 2
- 229960003444 immunosuppressant agent Drugs 0.000 description 2
- 239000003018 immunosuppressive agent Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- BNNZCELZKQKDQY-UHFFFAOYSA-N 1,3,2-oxazaphosphinan-2-ium 2-oxide Chemical compound O=[P+]1NCCCO1 BNNZCELZKQKDQY-UHFFFAOYSA-N 0.000 description 1
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 1
- JEHQWQCGNMNJFD-UHFFFAOYSA-N 2-[[but-3-enoxy-[2-chloroethyl(methyl)amino]phosphoryl]amino]ethyl methanesulfonate Chemical compound C=CCCOP(=O)(N(CCCl)C)NCCOS(C)(=O)=O JEHQWQCGNMNJFD-UHFFFAOYSA-N 0.000 description 1
- 125000005999 2-bromoethyl group Chemical group 0.000 description 1
- WAPXKKWUNSOPEL-UHFFFAOYSA-N 4-hydroperoxy-2h-oxazaphosphinine Chemical class OOC1=PNOC=C1 WAPXKKWUNSOPEL-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 101150065749 Churc1 gene Proteins 0.000 description 1
- 208000028018 Lymphocytic leukaemia Diseases 0.000 description 1
- 102100038239 Protein Churchill Human genes 0.000 description 1
- 241000246358 Thymus Species 0.000 description 1
- 235000007303 Thymus vulgaris Nutrition 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000005998 bromoethyl group Chemical group 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000000824 cytostatic agent Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000035931 haemagglutination Effects 0.000 description 1
- 230000003053 immunization Effects 0.000 description 1
- 238000002649 immunization Methods 0.000 description 1
- 230000001861 immunosuppressant effect Effects 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000036210 malignancy Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000001585 thymus vulgaris Substances 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
-
- 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/14—Esters of phosphoric acids containing P(=O)-halide groups
- C07F9/1403—Esters of phosphoric acids containing P(=O)-halide groups containing the structure Hal-P(=O)-O-unsaturated acyclic group
-
- 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/22—Amides of acids of phosphorus
- C07F9/24—Esteramides
- C07F9/2404—Esteramides the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/2412—Esteramides the ester moiety containing a substituent or a structure which is considered as characteristic of unsaturated acyclic alcohols
-
- 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/22—Amides of acids of phosphorus
- C07F9/24—Esteramides
- C07F9/2454—Esteramides the amide moiety containing a substituent or a structure which is considered as characteristic
- C07F9/2458—Esteramides the amide moiety containing a substituent or a structure which is considered as characteristic of aliphatic amines
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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP49133257A JPS5159886A (pt) | 1974-11-20 | 1974-11-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2552135A1 true DE2552135A1 (de) | 1976-05-26 |
Family
ID=15100374
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752552135 Withdrawn DE2552135A1 (de) | 1974-11-20 | 1975-11-20 | 4-hydroperoxy-tetrahydro-2h- 1,3,2-oxazaphosphorin-2-oxid-derivate |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS5159886A (pt) |
| AU (1) | AU500813B2 (pt) |
| CA (1) | CA1051914A (pt) |
| CH (1) | CH602777A5 (pt) |
| DE (1) | DE2552135A1 (pt) |
| FR (1) | FR2291763A1 (pt) |
| GB (1) | GB1527497A (pt) |
| NL (1) | NL7513590A (pt) |
| SE (1) | SE7513007L (pt) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2489825A1 (fr) * | 1980-09-10 | 1982-03-12 | Asta Werke Ag Chem Fab | 4-carbamoyloxy-oxazaphosphorines, procede pour leur preparation et compositions pharmaceutiques qui les contiennent |
| US4716242A (en) * | 1984-03-01 | 1987-12-29 | Asta-Werke Aktiengesellschaft Chemische Fabrik | Salts of oxazaphosphorine derivatives |
Families Citing this family (5)
| 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 |
| ATE255899T1 (de) * | 1999-05-24 | 2003-12-15 | Southern Res Inst | Isophosphoramide-senfgasanalogen und deren verwendung |
| US7678778B2 (en) | 2004-10-25 | 2010-03-16 | Dekk-Tec, Inc. | Salts of isophosphoramide mustard and analogs thereof as anti-tumor agents |
| US7964583B2 (en) | 2006-02-17 | 2011-06-21 | Ziopharm Oncology, Inc. | Salts of isophosphoramide mustard and analogs thereof as anti-tumor agents |
| BRPI0809999A2 (pt) | 2007-04-06 | 2014-10-14 | Ziopharm Oncology Inc | Sais de mostarda de isofosforamida e análogos da mesma |
-
1974
- 1974-11-20 JP JP49133257A patent/JPS5159886A/ja active Pending
-
1975
- 1975-11-07 CA CA239,381A patent/CA1051914A/en not_active Expired
- 1975-11-17 GB GB47320/75A patent/GB1527497A/en not_active Expired
- 1975-11-19 FR FR7535387A patent/FR2291763A1/fr not_active Withdrawn
- 1975-11-19 CH CH1500875A patent/CH602777A5/xx not_active IP Right Cessation
- 1975-11-19 SE SE7513007A patent/SE7513007L/xx unknown
- 1975-11-20 NL NL7513590A patent/NL7513590A/xx not_active Application Discontinuation
- 1975-11-20 AU AU86816/75A patent/AU500813B2/en not_active Expired
- 1975-11-20 DE DE19752552135 patent/DE2552135A1/de not_active Withdrawn
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2489825A1 (fr) * | 1980-09-10 | 1982-03-12 | Asta Werke Ag Chem Fab | 4-carbamoyloxy-oxazaphosphorines, procede pour leur preparation et compositions pharmaceutiques qui les contiennent |
| US4716242A (en) * | 1984-03-01 | 1987-12-29 | Asta-Werke Aktiengesellschaft Chemische Fabrik | Salts of oxazaphosphorine derivatives |
Also Published As
| Publication number | Publication date |
|---|---|
| CH602777A5 (pt) | 1978-07-31 |
| SE7513007L (sv) | 1976-05-21 |
| AU8681675A (en) | 1977-05-26 |
| AU500813B2 (en) | 1979-05-10 |
| JPS5159886A (pt) | 1976-05-25 |
| NL7513590A (nl) | 1976-05-24 |
| CA1051914A (en) | 1979-04-03 |
| GB1527497A (en) | 1978-10-04 |
| FR2291763A1 (fr) | 1976-06-18 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| AT395853B (de) | Neue imidazolderivate, verfahren zu ihrer herstellung und ihre verwendung | |
| DE2038320A1 (de) | Nichtwaessrige Wasserstoffperoxid-Loesungen | |
| DE2552135A1 (de) | 4-hydroperoxy-tetrahydro-2h- 1,3,2-oxazaphosphorin-2-oxid-derivate | |
| EP0416401B1 (de) | Verwendung von Phospholipid-Derivaten als antivirale Arzneimittel und neue Phospholipide | |
| EP0072531A1 (de) | Neue Cyclophosphamid-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung | |
| EP0072987A1 (de) | Neue cytostatisch wirksame Epoxidgruppen tragende 1,3,2-Oxazaphosphorin-Verbindungen, Verfahren zu ihrer Herstellung sowie ihre Verwendung in pharmazeutischen Zubereitungen | |
| CH628895A5 (en) | Process for the preparation of ergoline compounds | |
| DE2127812C2 (de) | 3-Methyl-7-phenyl-5H-pyrimido [1,2-a] [1,4] benzodiazepin-1-one und Verfahren zu deren Herstellung | |
| EP0112871A1 (de) | Derivate des n.n-bis(2-chlor-äthyl)-phosphorsäureamids. | |
| DE69911946T2 (de) | Phosphonsäure-diester-derivate | |
| DE2024299A1 (de) | Neue Sulfonamide, Verfahren zu ihrer Herstellung und ihre Verwendung in einem pharmazeutischen Präparat | |
| DE1299631B (de) | Phenylisopropylaminderivate und Verfahren zu ihrer Herstellung | |
| CH492738A (de) | Verfahren zur Herstellung von 2-(Bis-(2-chloräthyl)aminophenyl-4- -amino)-2H-1,3,2-oxazaphosphorin-tetrahydro-2-oxid | |
| US4085128A (en) | Cyclic phosphamide derivatives | |
| DE3212387A1 (de) | Glycerinphosphatide, verfahren zu ihrer herstellung und ihre verwendung in arzneimitteln | |
| CH644602A5 (de) | Benzothiazocin- und benzothiazoninderivate, ihre herstellung und diese derivate enthaltende pharmazeutische praeparate. | |
| DE1695092B2 (de) | N-(4-Sulfonamidophenyl)-a-alkylsuccinimide und deren Salze mit Basen, Verfahren zu ihrer Herstellung und pharmazeutische Zusammensetzungen | |
| DE2317178A1 (de) | 4-hydroxytetrahydro-2h-1,3,2-oxazaphosphorin-2-oxide, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel | |
| DE1445860C (de) | 5 (2 Nitrophenyl>7 nitro 1,2 dihydro 3H 1,4 benzodiazepinon (2)-denvate | |
| DE1695129A1 (de) | Verfahren zur Herstellung von Benzodiazepin-Derivaten | |
| AT304471B (de) | Verfahren zur Herstellung von neuen 1-sek.Amino-2-hydroxy-3-[(p-alkenyloxy- oder p-alkinyloxy)-phenoxy]propanen und ihren Säureadditionssalzen | |
| DE844897C (de) | Verfahren zur Herstellung von Diamidinderivaten | |
| CH636101A5 (en) | Process for preparing novel condensed derivatives of pyrimidine | |
| DE2822473A1 (de) | Alkanolaminderivate, verfahren zu ihrer herstellung und sie enthaltende pharmazeutische zusammensetzungen | |
| AT266080B (de) | Verfahren zur Herstellung der neuen 1-Isopropylamino-2-hydroxy-3-(o-niederalkoxymethyl-phenoxy)-propane und ihrer Salze |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8139 | Disposal/non-payment of the annual fee |