PL140732B1 - Method of obtaining 2-/2-halogenethylamino/-2-oxo-3-/2-halogenethylo/-1,3,2-oxazophosphorianytes - Google Patents
Method of obtaining 2-/2-halogenethylamino/-2-oxo-3-/2-halogenethylo/-1,3,2-oxazophosphorianytes Download PDFInfo
- Publication number
- PL140732B1 PL140732B1 PL1984249007A PL24900784A PL140732B1 PL 140732 B1 PL140732 B1 PL 140732B1 PL 1984249007 A PL1984249007 A PL 1984249007A PL 24900784 A PL24900784 A PL 24900784A PL 140732 B1 PL140732 B1 PL 140732B1
- Authority
- PL
- Poland
- Prior art keywords
- oxo
- oxazaphosphorinate
- enantiomeric
- racemic
- bromoethyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 25
- -1 2- bromoethylamino Chemical group 0.000 claims description 18
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 12
- 239000007864 aqueous solution Substances 0.000 claims description 9
- 229910000039 hydrogen halide Inorganic materials 0.000 claims description 9
- 239000012433 hydrogen halide Substances 0.000 claims description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 7
- 229910000042 hydrogen bromide Inorganic materials 0.000 claims description 6
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 238000007142 ring opening reaction Methods 0.000 claims description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 36
- 239000000243 solution Substances 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 8
- 239000010410 layer Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 7
- 239000012044 organic layer Substances 0.000 description 7
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- 238000001819 mass spectrum Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 239000011259 mixed solution Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- MDMOJTZZRGUJRS-UHFFFAOYSA-N OC(N1P=CC=CO1)=O Chemical class OC(N1P=CC=CO1)=O MDMOJTZZRGUJRS-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000000259 anti-tumor effect Effects 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- HOMGKSMUEGBAAB-UHFFFAOYSA-N ifosfamide Chemical compound ClCCNP1(=O)OCCCN1CCCl HOMGKSMUEGBAAB-UHFFFAOYSA-N 0.000 description 2
- 229960001101 ifosfamide Drugs 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 125000005999 2-bromoethyl group Chemical group 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 229940041181 antineoplastic drug Drugs 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- UXTMROKLAAOEQO-UHFFFAOYSA-N chloroform;ethanol Chemical compound CCO.ClC(Cl)Cl UXTMROKLAAOEQO-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000003791 organic solvent mixture Substances 0.000 description 1
- 230000006340 racemization Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229960001866 silicon dioxide Drugs 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)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL1984249007A PL140732B1 (en) | 1984-07-31 | 1984-07-31 | Method of obtaining 2-/2-halogenethylamino/-2-oxo-3-/2-halogenethylo/-1,3,2-oxazophosphorianytes |
| US06/758,484 US4684742A (en) | 1984-07-31 | 1985-07-24 | Process for the production of 2-(2-halogenoethylamino)-2-oxo-3-(2-halogenoethyl)-1.3.2.-oxazaphosphorinanes |
| JP60169666A JPS6143194A (ja) | 1984-07-31 | 1985-07-31 | ２‐（２‐ハロゲノエチルアミノ）‐２‐オキソ‐３‐（２‐ハロゲノエチル）‐１，３，２‐オキサザホスホリナン類の製造方法 |
| DE19853527504 DE3527504A1 (de) | 1984-07-31 | 1985-07-31 | Verfahren zur herstellung von 2-(2-halogenethylamin)-2-oxo-3-(2-halogenethyl)-1.3.2-oxazaphosphorinan |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL1984249007A PL140732B1 (en) | 1984-07-31 | 1984-07-31 | Method of obtaining 2-/2-halogenethylamino/-2-oxo-3-/2-halogenethylo/-1,3,2-oxazophosphorianytes |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL249007A1 PL249007A1 (en) | 1986-02-11 |
| PL140732B1 true PL140732B1 (en) | 1987-05-30 |
Family
ID=20022903
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1984249007A PL140732B1 (en) | 1984-07-31 | 1984-07-31 | Method of obtaining 2-/2-halogenethylamino/-2-oxo-3-/2-halogenethylo/-1,3,2-oxazophosphorianytes |
Country Status (4)
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2416015A1 (en) * | 2000-07-18 | 2002-01-24 | Leo Pharma A/S | Matrix metalloproteinase inhibitors |
| AU2003205544A1 (en) * | 2002-01-18 | 2003-07-30 | Leo Pharma A/S | Mmp inhibitors |
| US6613927B1 (en) | 2002-02-08 | 2003-09-02 | American Pharmaceutical Partners, Inc. | Sterile lyophilized ifosfamide and associated methods |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1645922A1 (de) * | 1966-07-11 | 1971-01-28 | Asta Werke Ag Chem Fab | Verfahren zur Herstellung von N,N'-Bis-halogenalkylphosphorsaeure-und -thiophosphorsaeureesteramiden |
| FR1530936A (fr) * | 1967-07-10 | 1968-06-28 | Kanegafuchi Chemical Ind | Procédé pour empêcher la formation de polymère de chloroprène perlé |
-
1984
- 1984-07-31 PL PL1984249007A patent/PL140732B1/pl unknown
-
1985
- 1985-07-24 US US06/758,484 patent/US4684742A/en not_active Expired - Lifetime
- 1985-07-31 DE DE19853527504 patent/DE3527504A1/de active Granted
- 1985-07-31 JP JP60169666A patent/JPS6143194A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| DE3527504A1 (de) | 1986-02-06 |
| US4684742A (en) | 1987-08-04 |
| DE3527504C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1988-04-14 |
| PL249007A1 (en) | 1986-02-11 |
| JPS6143194A (ja) | 1986-03-01 |
| JPH0244835B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1990-10-05 |
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