LU83613A1 - 4-carbamoyloxy-oxazaphosporine,verfahren zu ihrer herstellung und diese enthaltende pharmazeutische zubereitungen - Google Patents
4-carbamoyloxy-oxazaphosporine,verfahren zu ihrer herstellung und diese enthaltende pharmazeutische zubereitungen Download PDFInfo
- Publication number
- LU83613A1 LU83613A1 LU83613A LU83613A LU83613A1 LU 83613 A1 LU83613 A1 LU 83613A1 LU 83613 A LU83613 A LU 83613A LU 83613 A LU83613 A LU 83613A LU 83613 A1 LU83613 A1 LU 83613A1
- Authority
- LU
- Luxembourg
- Prior art keywords
- hydrogen
- alkyl
- phenyl
- substituted
- formula
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 8
- 239000000825 pharmaceutical preparation Substances 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title description 2
- -1 2-methanesulfonyloxyethyl Chemical group 0.000 claims description 33
- 239000001257 hydrogen Substances 0.000 claims description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims description 25
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
- 229910052740 iodine Inorganic materials 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 claims description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- VZZWPFPWQGVAHK-UHFFFAOYSA-N 2h-oxazaphosphinin-4-yl carbamate Chemical compound NC(=O)OC1=PNOC=C1 VZZWPFPWQGVAHK-UHFFFAOYSA-N 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 238000001816 cooling Methods 0.000 claims description 5
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- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 229910052717 sulfur Chemical group 0.000 claims description 4
- IZJCEZHCNFRDKR-UHFFFAOYSA-N 4-ethoxy-2h-oxazaphosphinine Chemical compound CCOC1=PNOC=C1 IZJCEZHCNFRDKR-UHFFFAOYSA-N 0.000 claims description 3
- DRAJWRKLRBNJRQ-UHFFFAOYSA-N Hydroxycarbamic acid Chemical class ONC(O)=O DRAJWRKLRBNJRQ-UHFFFAOYSA-N 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 150000002923 oximes Chemical class 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
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- 125000004429 atom Chemical group 0.000 claims description 2
- 125000004069 aziridinyl group Chemical group 0.000 claims description 2
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- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 claims description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 2
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- 238000010438 heat treatment Methods 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
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- 239000000126 substance Substances 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 239000011593 sulfur Chemical group 0.000 claims description 2
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 2
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- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
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- KMUZEPMBBDHYBC-UHFFFAOYSA-N 2-(hydroxycarbamoylamino)acetic acid Chemical compound ONC(=O)NCC(O)=O KMUZEPMBBDHYBC-UHFFFAOYSA-N 0.000 description 3
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 description 3
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- 125000006239 protecting group Chemical group 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 229960000875 trofosfamide Drugs 0.000 description 1
- UMKFEPPTGMDVMI-UHFFFAOYSA-N trofosfamide Chemical compound ClCCN(CCCl)P1(=O)OCCCN1CCCl UMKFEPPTGMDVMI-UHFFFAOYSA-N 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 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)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8029222 | 1980-09-10 | ||
| GB8029222 | 1980-09-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| LU83613A1 true LU83613A1 (de) | 1982-01-21 |
Family
ID=10515985
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LU83613A LU83613A1 (de) | 1980-09-10 | 1981-09-07 | 4-carbamoyloxy-oxazaphosporine,verfahren zu ihrer herstellung und diese enthaltende pharmazeutische zubereitungen |
Country Status (29)
| Country | Link |
|---|---|
| JP (1) | JPS5785396A (pt) |
| AR (1) | AR231989A1 (pt) |
| AT (1) | AT386210B (pt) |
| AU (1) | AU538275B2 (pt) |
| BE (1) | BE890276A (pt) |
| CA (2) | CA1161453A (pt) |
| CH (1) | CH650787A5 (pt) |
| CS (1) | CS227680B2 (pt) |
| DD (1) | DD202166A5 (pt) |
| DE (1) | DE3133309A1 (pt) |
| DK (1) | DK400481A (pt) |
| EG (1) | EG15392A (pt) |
| ES (1) | ES505324A0 (pt) |
| FI (1) | FI70026C (pt) |
| FR (1) | FR2489825A1 (pt) |
| GR (1) | GR75300B (pt) |
| HU (1) | HU185953B (pt) |
| IE (1) | IE51784B1 (pt) |
| IL (1) | IL63661A (pt) |
| IT (2) | IT1198350B (pt) |
| LU (1) | LU83613A1 (pt) |
| NL (1) | NL8104093A (pt) |
| NO (1) | NO161261C (pt) |
| PL (1) | PL128627B1 (pt) |
| PT (1) | PT73645B (pt) |
| RO (1) | RO83972B (pt) |
| SE (1) | SE458203B (pt) |
| YU (1) | YU42584B (pt) |
| ZA (1) | ZA815922B (pt) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0158057B1 (de) * | 1984-03-01 | 1989-04-26 | ASTA Pharma AG | Neue Salze von Oxazaphosphorin-Derivaten |
| ZA851062B (en) * | 1984-03-01 | 1985-11-27 | Asta Werke Ag Chem Fab | Salts of oxazaphosphorine derivatives and process for their production |
| WO2016089208A2 (en) | 2014-12-04 | 2016-06-09 | Stichting Maastricht Radiation Oncology "Maastro-Clinic" | Sulfonamide, sulfamate and sulfamide derivatives of anti-cancer agents |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA955937A (en) * | 1971-06-28 | 1974-10-08 | Shionogi And Co. Ltd. | Cyclic phosphamide derivatives |
| US3911005A (en) * | 1974-09-12 | 1975-10-07 | Monsanto Co | 1,3,2-Diazaphospholidine compounds |
| JPS5159886A (pt) * | 1974-11-20 | 1976-05-25 | Shionogi Seiyaku Kk |
-
1981
- 1981-08-22 DE DE19813133309 patent/DE3133309A1/de active Granted
- 1981-08-25 IE IE1951/81A patent/IE51784B1/en unknown
- 1981-08-26 ZA ZA815922A patent/ZA815922B/xx unknown
- 1981-08-26 AU AU74657/81A patent/AU538275B2/en not_active Ceased
- 1981-08-26 IL IL63661A patent/IL63661A/xx not_active IP Right Cessation
- 1981-08-31 CH CH5584/81A patent/CH650787A5/de not_active IP Right Cessation
- 1981-08-31 GR GR65896A patent/GR75300B/el unknown
- 1981-09-03 NL NL8104093A patent/NL8104093A/xx not_active Application Discontinuation
- 1981-09-04 CS CS816537A patent/CS227680B2/cs unknown
- 1981-09-07 AT AT0386481A patent/AT386210B/de not_active IP Right Cessation
- 1981-09-07 LU LU83613A patent/LU83613A1/de unknown
- 1981-09-08 SE SE8105340A patent/SE458203B/sv not_active IP Right Cessation
- 1981-09-08 RO RO105257A patent/RO83972B/ro unknown
- 1981-09-08 FR FR8116999A patent/FR2489825A1/fr active Granted
- 1981-09-08 DD DD81233132A patent/DD202166A5/de unknown
- 1981-09-08 EG EG508/81A patent/EG15392A/xx active
- 1981-09-08 HU HU812580A patent/HU185953B/hu unknown
- 1981-09-09 ES ES505324A patent/ES505324A0/es active Granted
- 1981-09-09 CA CA000385516A patent/CA1161453A/en not_active Expired
- 1981-09-09 PL PL1981232960A patent/PL128627B1/pl unknown
- 1981-09-09 JP JP56141108A patent/JPS5785396A/ja active Granted
- 1981-09-09 FI FI812798A patent/FI70026C/fi not_active IP Right Cessation
- 1981-09-09 BE BE2/59345A patent/BE890276A/fr not_active IP Right Cessation
- 1981-09-09 IT IT23860/81A patent/IT1198350B/it active
- 1981-09-09 DK DK400481A patent/DK400481A/da not_active Application Discontinuation
- 1981-09-09 PT PT73645A patent/PT73645B/pt unknown
- 1981-09-09 NO NO813063A patent/NO161261C/no unknown
- 1981-09-10 YU YU2179/81A patent/YU42584B/xx unknown
- 1981-09-10 AR AR286736A patent/AR231989A1/es active
-
1984
- 1984-05-30 CA CA000455507A patent/CA1184563B/en not_active Expired
- 1984-06-12 IT IT21372/84A patent/IT1220985B/it active
Also Published As
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