JPS5843396B2 - １，３，２−オキサアザホスフア−環状化合物のアルキルスルホン酸エステル類の製法 - Google Patents
１，３，２−オキサアザホスフア−環状化合物のアルキルスルホン酸エステル類の製法Info
- Publication number
- JPS5843396B2 JPS5843396B2 JP55152998A JP15299880A JPS5843396B2 JP S5843396 B2 JPS5843396 B2 JP S5843396B2 JP 55152998 A JP55152998 A JP 55152998A JP 15299880 A JP15299880 A JP 15299880A JP S5843396 B2 JPS5843396 B2 JP S5843396B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- halogen atom
- group
- solution
- ether
- 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.)
- Expired
Links
- -1 alkyl sulfonic acid esters Chemical class 0.000 title claims description 11
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 40
- 125000005843 halogen group Chemical group 0.000 claims description 26
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 6
- 125000005947 C1-C6 alkylsulfonyloxy group Chemical group 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
- 230000000737 periodic effect Effects 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 96
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 84
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 57
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 41
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 27
- 239000003921 oil Substances 0.000 description 26
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 26
- 239000000047 product Substances 0.000 description 25
- 238000003756 stirring Methods 0.000 description 22
- 239000000203 mixture Substances 0.000 description 21
- 239000000706 filtrate Substances 0.000 description 18
- 238000002844 melting Methods 0.000 description 13
- 230000008018 melting Effects 0.000 description 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 12
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 9
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 239000013078 crystal Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000004587 chromatography analysis Methods 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 239000012259 ether extract Substances 0.000 description 4
- 230000001506 immunosuppresive effect Effects 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- SBMJSKYKTAAHAB-UHFFFAOYSA-N 2-chloro-3-(2-chloroethyl)-1,3,2$l^{5}-oxazaphosphinane 2-oxide Chemical compound ClCCN1CCCOP1(Cl)=O SBMJSKYKTAAHAB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- JYCULSYEFRCGNR-UHFFFAOYSA-N O=P1OC=CC=N1 Chemical compound O=P1OC=CC=N1 JYCULSYEFRCGNR-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000012230 colorless oil Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- MLKQJVFHEUORBO-UHFFFAOYSA-M silver;methanesulfonate Chemical compound [Ag+].CS([O-])(=O)=O MLKQJVFHEUORBO-UHFFFAOYSA-M 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 229910021607 Silver chloride Inorganic materials 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 238000011081 inoculation Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 239000011877 solvent mixture Substances 0.000 description 2
- KODLUXHSIZOKTG-UHFFFAOYSA-N 1-aminobutan-2-ol Chemical compound CCC(O)CN KODLUXHSIZOKTG-UHFFFAOYSA-N 0.000 description 1
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 1
- HFPDWZDOAAAUSY-UHFFFAOYSA-N 2-(2-chloroethylamino)ethanol;hydrochloride Chemical compound Cl.OCCNCCCl HFPDWZDOAAAUSY-UHFFFAOYSA-N 0.000 description 1
- BQHMRVKGQBPYPQ-UHFFFAOYSA-N 2-[[3-(2-chloroethyl)-2-oxo-1,3,2lambda5-oxazaphosphinan-2-yl]amino]ethanol Chemical compound OCCNP1(OCCCN1CCCl)=O BQHMRVKGQBPYPQ-UHFFFAOYSA-N 0.000 description 1
- IDTWVPMJKFNWJF-UHFFFAOYSA-N 2-[[3-(2-methylsulfonyloxyethyl)-2-oxo-1,3,2lambda5-oxazaphosphinan-2-yl]amino]ethyl methanesulfonate Chemical compound S(=O)(=O)(C)OCCNP1(OCCCN1CCOS(=O)(=O)C)=O IDTWVPMJKFNWJF-UHFFFAOYSA-N 0.000 description 1
- ONRREFWJTRBDRA-UHFFFAOYSA-N 2-chloroethanamine;hydron;chloride Chemical compound [Cl-].[NH3+]CCCl ONRREFWJTRBDRA-UHFFFAOYSA-N 0.000 description 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- XTIRDZXXEUOETP-UHFFFAOYSA-N Br.S(=O)(=O)(C)OCCCNCCCOS(=O)(=O)C Chemical compound Br.S(=O)(=O)(C)OCCCNCCCOS(=O)(=O)C XTIRDZXXEUOETP-UHFFFAOYSA-N 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 1
- UJJLHBABNGSWCM-UHFFFAOYSA-N O=P1=CC=CC=N1 Chemical compound O=P1=CC=CC=N1 UJJLHBABNGSWCM-UHFFFAOYSA-N 0.000 description 1
- ZAMZJYJIKWEAEO-UHFFFAOYSA-N OCCNP1(OCCCN1CCCCl)=O Chemical compound OCCNP1(OCCCN1CCCCl)=O ZAMZJYJIKWEAEO-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 239000000427 antigen Substances 0.000 description 1
- 102000036639 antigens Human genes 0.000 description 1
- 108091007433 antigens Proteins 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- QLRGSUBBRSJVLL-UHFFFAOYSA-N benzene;chloroform;methanol Chemical compound OC.ClC(Cl)Cl.C1=CC=CC=C1 QLRGSUBBRSJVLL-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- FRYHCSODNHYDPU-UHFFFAOYSA-N ethanesulfonyl chloride Chemical compound CCS(Cl)(=O)=O FRYHCSODNHYDPU-UHFFFAOYSA-N 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
- 150000004820 halides Chemical class 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 241000411851 herbal medicine Species 0.000 description 1
- 230000005965 immune activity Effects 0.000 description 1
- 230000036039 immunity Effects 0.000 description 1
- 230000016784 immunoglobulin production Effects 0.000 description 1
- DBIGHPPNXATHOF-UHFFFAOYSA-N improsulfan Chemical compound CS(=O)(=O)OCCCNCCCOS(C)(=O)=O DBIGHPPNXATHOF-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 210000003127 knee Anatomy 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- PWQOZRPSDQKNPW-UHFFFAOYSA-N pentane-1-sulfonyl chloride Chemical compound CCCCCS(Cl)(=O)=O PWQOZRPSDQKNPW-UHFFFAOYSA-N 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- UXCDUFKZSUBXGM-UHFFFAOYSA-N phosphoric tribromide Chemical compound BrP(Br)(Br)=O UXCDUFKZSUBXGM-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- DRINJBFRTLBHNF-UHFFFAOYSA-N propane-2-sulfonyl chloride Chemical compound CC(C)S(Cl)(=O)=O DRINJBFRTLBHNF-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 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
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- 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
- C07F9/65844—Cyclic amide derivatives of acids of phosphorus, in which one nitrogen atom belongs to the ring the phosphorus atom being part of a five-membered ring which may be condensed with another ring system
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Immunology (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Transplantation (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2107936A DE2107936C3 (de) | 1971-02-19 | 1971-02-19 | Alkylsulfonsäureester von 2-Oxo-13,2-oxazaphosphorinanen und diese enthaltende pharmazeutische Präparate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5697293A JPS5697293A (en) | 1981-08-05 |
| JPS5843396B2 true JPS5843396B2 (ja) | 1983-09-27 |
Family
ID=5799224
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP55152998A Expired JPS5843396B2 (ja) | 1971-02-19 | 1980-11-01 | １，３，２−オキサアザホスフア−環状化合物のアルキルスルホン酸エステル類の製法 |
| JP55152999A Expired JPS591716B2 (ja) | 1971-02-19 | 1980-11-01 | １，３，２−オキサアザホスフア−環状化合物のアルキルスルホン酸エステル類の製法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP55152999A Expired JPS591716B2 (ja) | 1971-02-19 | 1980-11-01 | １，３，２−オキサアザホスフア−環状化合物のアルキルスルホン酸エステル類の製法 |
Country Status (7)
| Country | Link |
|---|---|
| JP (2) | JPS5843396B2 (enExample) |
| AT (1) | AT311381B (enExample) |
| CS (1) | CS167967B2 (enExample) |
| DE (1) | DE2107936C3 (enExample) |
| GB (1) | GB1341170A (enExample) |
| SU (3) | SU453845A3 (enExample) |
| ZA (1) | ZA72740B (enExample) |
Families Citing this family (2)
| 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 |
| FR2661433B1 (fr) * | 1990-04-26 | 1994-06-03 | Scerer | Dalle de chaussee d'un pont, notamment de grande portee. |
-
1971
- 1971-02-19 DE DE2107936A patent/DE2107936C3/de not_active Expired
-
1972
- 1972-02-04 AT AT91272A patent/AT311381B/de not_active IP Right Cessation
- 1972-02-04 ZA ZA720740A patent/ZA72740B/xx unknown
- 1972-02-15 CS CS965A patent/CS167967B2/cs unknown
- 1972-02-18 SU SU1749700A patent/SU453845A3/ru active
- 1972-02-18 SU SU1920572A patent/SU461510A3/ru active
- 1972-02-21 GB GB788172A patent/GB1341170A/en not_active Expired
-
1973
- 1973-05-16 SU SU1920105A patent/SU518137A3/ru active
-
1980
- 1980-11-01 JP JP55152998A patent/JPS5843396B2/ja not_active Expired
- 1980-11-01 JP JP55152999A patent/JPS591716B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| ZA72740B (en) | 1972-10-25 |
| CS167967B2 (enExample) | 1976-05-28 |
| JPS591716B2 (ja) | 1984-01-13 |
| DE2107936B2 (de) | 1977-10-20 |
| GB1341170A (en) | 1973-12-19 |
| JPS5697293A (en) | 1981-08-05 |
| JPS5697294A (en) | 1981-08-05 |
| SU518137A3 (ru) | 1976-06-15 |
| AT311381B (de) | 1973-11-12 |
| DE2107936A1 (de) | 1972-09-07 |
| SU453845A3 (ru) | 1974-12-15 |
| DE2107936C3 (de) | 1978-06-08 |
| SU461510A3 (ru) | 1975-02-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| AU682050B2 (en) | Adhesion receptor antagonists | |
| DE69108138T2 (de) | Imidazopyridinderivate und ihre Verwendung. | |
| NO123128B (enExample) | ||
| HU210746B (en) | Process for preparation of new sulfonamides derived from benzocyclic or benzoheterocyclic acids, and pharmaceuticals containing them | |
| PT87660B (pt) | Processo para a preparacao de derivados de labdano polioxigenados e de composicoes farmaceuticas que os contem | |
| JPS5843396B2 (ja) | １，３，２−オキサアザホスフア−環状化合物のアルキルスルホン酸エステル類の製法 | |
| US2499352A (en) | Substituted glycinamides | |
| EP0009608B1 (en) | N-phenethylacetamide compounds, processes for their preparation and therapeutic compositions containing them | |
| AU2007309558B2 (en) | Crystal modifications -3- (1H-indol-3-yl) -4- [2- (4-methyl-piperazin-1-yl) -quinazolin-4-yl] -pyrrole-2, 5-dione | |
| US2449638A (en) | Substituted glycinamides | |
| US2882275A (en) | 1-p-nitrophenyl-2-azidoacetylaminopropane derivatives | |
| EP0221806B1 (en) | Substituted thiophene-2-sulfanomide and antiglaucoma compositions containing them | |
| JPH02209852A (ja) | ヒドロキシプロパフェノングリセリド及びその製造方法 | |
| US3729477A (en) | Certain 4-(3-amino-2-hydroxypropoxy)-1,2,5-thiadiazole-3-carboxamides | |
| US3378592A (en) | Process for the production of 3, 4-dihydroxybenzyloxyaminehydrobromide | |
| CN109496215B (zh) | 一种福沙匹坦磷酸酯中间体及其制备方法 | |
| US2762804A (en) | 3-methyl-5-phenyl-2, 6-piperazinedione and derivatives thereof and method of preparing same | |
| JPS5934194B2 (ja) | 複素環式化合物の製造法 | |
| US2374367A (en) | Process for preparing therapeutically active substances | |
| US1073380A (en) | N-halogenalkyl-c c-dialkylbarbituric acids and preparation of the same. | |
| US3124589A (en) | Certain z-alkylamino polymethylene | |
| US3444167A (en) | Process for the production of thiamine derivatives | |
| KR820000521B1 (ko) | 페닐에탄올아민 유도체의 제조 방법 | |
| US2890219A (en) | Chjohichinohichio-co- | |
| JPH03503900A (ja) | 複素環式スルホニルニトロメタン、その製造法および医薬製剤 |