FI56387C - Foerfarande foer framstaellning av alkansulfonsyraestrar av 1,3,2-oxazafosforinfoereningar med immunitetssaenkande verkan - Google Patents
Foerfarande foer framstaellning av alkansulfonsyraestrar av 1,3,2-oxazafosforinfoereningar med immunitetssaenkande verkan Download PDFInfo
- Publication number
- FI56387C FI56387C FI445/72A FI44572A FI56387C FI 56387 C FI56387 C FI 56387C FI 445/72 A FI445/72 A FI 445/72A FI 44572 A FI44572 A FI 44572A FI 56387 C FI56387 C FI 56387C
- Authority
- FI
- Finland
- Prior art keywords
- group
- formula
- alk
- same
- chloroethyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 70
- -1 β-chloroethyl group Chemical group 0.000 claims description 43
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
- 125000005843 halogen group Chemical group 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 230000001506 immunosuppresive effect Effects 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 3
- MXZROAOUCUVNHX-UHFFFAOYSA-N 2-Aminopropanol Chemical compound CCC(N)O MXZROAOUCUVNHX-UHFFFAOYSA-N 0.000 claims description 2
- MIQVAKCNWBAWPC-UHFFFAOYSA-N 2h-1,3,2-oxazaphosphinine Chemical class O1PN=CC=C1 MIQVAKCNWBAWPC-UHFFFAOYSA-N 0.000 claims description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
- 239000005977 Ethylene Substances 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 230000000737 periodic effect Effects 0.000 claims description 2
- 101001053401 Arabidopsis thaliana Acid beta-fructofuranosidase 3, vacuolar Proteins 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 206010061598 Immunodeficiency Diseases 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 137
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 111
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 104
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 53
- 239000003921 oil Substances 0.000 description 45
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 40
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 34
- 239000000706 filtrate Substances 0.000 description 31
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 29
- 238000003756 stirring Methods 0.000 description 29
- 238000000967 suction filtration Methods 0.000 description 21
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 19
- 239000000203 mixture Substances 0.000 description 16
- 239000002904 solvent Substances 0.000 description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- 238000001704 evaporation Methods 0.000 description 15
- 230000008020 evaporation Effects 0.000 description 15
- 238000001816 cooling Methods 0.000 description 13
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
- SBMJSKYKTAAHAB-UHFFFAOYSA-N 2-chloro-3-(2-chloroethyl)-1,3,2$l^{5}-oxazaphosphinane 2-oxide Chemical compound ClCCN1CCCOP1(Cl)=O SBMJSKYKTAAHAB-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 238000001035 drying Methods 0.000 description 7
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- GLVAUDGFNGKCSF-UHFFFAOYSA-N mercaptopurine Chemical compound S=C1NC=NC2=C1NC=N2 GLVAUDGFNGKCSF-UHFFFAOYSA-N 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- 238000000926 separation method Methods 0.000 description 6
- ZSZKJARKHWCBJK-UHFFFAOYSA-N 2-[[3-(2-chloroethyl)-2-oxo-1,3,2$l^{5}-oxazaphosphinan-2-yl]amino]ethyl methanesulfonate Chemical compound CS(=O)(=O)OCCNP1(=O)OCCCN1CCCl ZSZKJARKHWCBJK-UHFFFAOYSA-N 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 239000012230 colorless oil Substances 0.000 description 5
- 238000004440 column chromatography Methods 0.000 description 5
- 239000005457 ice water Substances 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- UBRSKPGONDTDNE-UHFFFAOYSA-N 3-(2-chloroethylamino)propan-1-ol;hydrochloride Chemical compound Cl.OCCCNCCCl UBRSKPGONDTDNE-UHFFFAOYSA-N 0.000 description 4
- 206010062016 Immunosuppression Diseases 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- 239000007832 Na2SO4 Substances 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- NPOMSUOUAZCMBL-UHFFFAOYSA-N dichloromethane;ethoxyethane Chemical compound ClCCl.CCOCC NPOMSUOUAZCMBL-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000012259 ether extract Substances 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 230000003053 immunization Effects 0.000 description 4
- 238000002649 immunization Methods 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- MLKQJVFHEUORBO-UHFFFAOYSA-M silver;methanesulfonate Chemical compound [Ag+].CS([O-])(=O)=O MLKQJVFHEUORBO-UHFFFAOYSA-M 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- 241000589562 Brucella Species 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 229910021607 Silver chloride Inorganic materials 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 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
- 239000003610 charcoal Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000028993 immune response Effects 0.000 description 3
- 229960001428 mercaptopurine Drugs 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- BUMJLYRPNLZBCW-UHFFFAOYSA-N 3-[2-[bis(2-chloroethyl)amino]-2-oxo-1,3,2$l^{5}-oxazaphosphinan-3-yl]propyl methanesulfonate Chemical compound CS(=O)(=O)OCCCN1CCCOP1(=O)N(CCCl)CCCl BUMJLYRPNLZBCW-UHFFFAOYSA-N 0.000 description 2
- LDJYQUUXVWTUMZ-UHFFFAOYSA-N 3-[3-methylsulfonyloxypropyl-(2-oxo-1,3,2$l^{5}-oxazaphosphinan-2-yl)amino]propyl methanesulfonate Chemical compound CS(=O)(=O)OCCCN(CCCOS(C)(=O)=O)P1(=O)NCCCO1 LDJYQUUXVWTUMZ-UHFFFAOYSA-N 0.000 description 2
- XLUZYXOJKKKJLS-UHFFFAOYSA-N 3-[[3-(2-chloroethyl)-2-oxo-1,3,2$l^{5}-oxazaphosphinan-2-yl]amino]propyl methanesulfonate Chemical compound CS(=O)(=O)OCCCNP1(=O)OCCCN1CCCl XLUZYXOJKKKJLS-UHFFFAOYSA-N 0.000 description 2
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- LMEKQMALGUDUQG-UHFFFAOYSA-N azathioprine Chemical compound CN1C=NC([N+]([O-])=O)=C1SC1=NC=NC2=C1NC=N2 LMEKQMALGUDUQG-UHFFFAOYSA-N 0.000 description 2
- 229960002170 azathioprine Drugs 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229960002092 busulfan Drugs 0.000 description 2
- 230000002140 halogenating effect Effects 0.000 description 2
- HOMGKSMUEGBAAB-UHFFFAOYSA-N ifosfamide Chemical compound ClCCNP1(=O)OCCCN1CCCl HOMGKSMUEGBAAB-UHFFFAOYSA-N 0.000 description 2
- 230000006058 immune tolerance Effects 0.000 description 2
- 239000003018 immunosuppressive agent Substances 0.000 description 2
- 229940125721 immunosuppressive agent Drugs 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 238000011081 inoculation Methods 0.000 description 2
- 229940098779 methanesulfonic acid Drugs 0.000 description 2
- 238000010899 nucleation Methods 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000011877 solvent mixture Substances 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- YARLDADICWCIGA-UHFFFAOYSA-N 1-(2-chloroethylamino)propan-1-ol Chemical compound ClCCNC(CC)O YARLDADICWCIGA-UHFFFAOYSA-N 0.000 description 1
- JYJSNYJEEVWYCO-UHFFFAOYSA-N 1-[[3-(2-chloroethyl)-2-oxo-1,3,2$l^{5}-oxazaphosphinan-2-yl]amino]propan-2-yl methanesulfonate Chemical compound CS(=O)(=O)OC(C)CNP1(=O)OCCCN1CCCl JYJSNYJEEVWYCO-UHFFFAOYSA-N 0.000 description 1
- CKFSKQWHDKANOI-UHFFFAOYSA-N 1-[[3-(2-chloroethyl)-2-oxo-1,3,2lambda5-oxazaphosphinan-2-yl]amino]propan-2-ol Chemical compound OC(CNP1(OCCCN1CCCl)=O)C CKFSKQWHDKANOI-UHFFFAOYSA-N 0.000 description 1
- 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
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 1
- MIJDSYMOBYNHOT-UHFFFAOYSA-N 2-(ethylamino)ethanol Chemical compound CCNCCO MIJDSYMOBYNHOT-UHFFFAOYSA-N 0.000 description 1
- SOKCKTKWDABGHV-UHFFFAOYSA-N 2-[(3-ethyl-2-oxo-1,3,2$l^{5}-oxazaphosphinan-2-yl)amino]ethyl methanesulfonate Chemical compound CCN1CCCOP1(=O)NCCOS(C)(=O)=O SOKCKTKWDABGHV-UHFFFAOYSA-N 0.000 description 1
- YAYVNPIXOHXJPJ-UHFFFAOYSA-N 2-[2-(2-chloroethylamino)-2-oxo-1,3,2$l^{5}-oxazaphosphinan-3-yl]ethyl methanesulfonate Chemical compound CS(=O)(=O)OCCN1CCCOP1(=O)NCCCl YAYVNPIXOHXJPJ-UHFFFAOYSA-N 0.000 description 1
- HMGJHQGDFPHSAR-UHFFFAOYSA-N 2-[[3-(2-chloroethyl)-2-oxido-1,3,2-oxazaphosphinan-2-ium-2-yl]amino]butyl methanesulfonate Chemical compound CS(=O)(=O)OCC(CC)N[P+]1([O-])OCCCN1CCCl HMGJHQGDFPHSAR-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
- KTJQXXIVWRXBCC-UHFFFAOYSA-N 2-chloro-1,3,2$l^{5}-oxazaphosphinane 2-oxide Chemical compound ClP1(=O)NCCCO1 KTJQXXIVWRXBCC-UHFFFAOYSA-N 0.000 description 1
- NKRLFWXSRKGPOE-UHFFFAOYSA-N 2-hydroxyoxazaphosphinine Chemical compound ON1OC=CC=P1 NKRLFWXSRKGPOE-UHFFFAOYSA-N 0.000 description 1
- RNHZZBODUNBXRP-UHFFFAOYSA-N 3-[2-(2-chloroethylamino)-2-oxo-1,3,2$l^{5}-oxazaphosphinan-3-yl]propyl methanesulfonate Chemical compound CS(=O)(=O)OCCCN1CCCOP1(=O)NCCCl RNHZZBODUNBXRP-UHFFFAOYSA-N 0.000 description 1
- YSRITDNKCCBFCR-UHFFFAOYSA-N 3-[2-[bis(2-chloroethyl)amino]-2-oxo-1,3,2lambda5-oxazaphosphinan-3-yl]propan-1-ol Chemical compound ClCCN(P1(OCCCN1CCCO)=O)CCCl YSRITDNKCCBFCR-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-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
- CKRWWKDTFDFVCH-UHFFFAOYSA-N CS(=O)(=O)OCCNP1(=O)OCCCN1CCCCl Chemical compound CS(=O)(=O)OCCNP1(=O)OCCCN1CCCCl CKRWWKDTFDFVCH-UHFFFAOYSA-N 0.000 description 1
- MBJSOEPSMJYKQQ-UHFFFAOYSA-N CS(OCCCN(CCCl)P(O)(O)=O)(=O)=O.Cl.Cl Chemical compound CS(OCCCN(CCCl)P(O)(O)=O)(=O)=O.Cl.Cl MBJSOEPSMJYKQQ-UHFFFAOYSA-N 0.000 description 1
- VZOYIALJXDZTJY-UHFFFAOYSA-N CS(OCCN(CCCl)P(O)(O)=O)(=O)=O.Cl.Cl Chemical compound CS(OCCN(CCCl)P(O)(O)=O)(=O)=O.Cl.Cl VZOYIALJXDZTJY-UHFFFAOYSA-N 0.000 description 1
- NHNKGVKEERKBOA-UHFFFAOYSA-N CS(OCCNP(O)(O)=O)(=O)=O.Cl.Cl Chemical compound CS(OCCNP(O)(O)=O)(=O)=O.Cl.Cl NHNKGVKEERKBOA-UHFFFAOYSA-N 0.000 description 1
- 101150065749 Churc1 gene Proteins 0.000 description 1
- VUVFECZJSWRIAQ-UHFFFAOYSA-N ClP1(OC(CCN1CCCl)C)=O Chemical compound ClP1(OC(CCN1CCCl)C)=O VUVFECZJSWRIAQ-UHFFFAOYSA-N 0.000 description 1
- 101710154606 Hemagglutinin Proteins 0.000 description 1
- 241000186779 Listeria monocytogenes Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 1
- ZAMZJYJIKWEAEO-UHFFFAOYSA-N OCCNP1(OCCCN1CCCCl)=O Chemical compound OCCNP1(OCCCN1CCCCl)=O ZAMZJYJIKWEAEO-UHFFFAOYSA-N 0.000 description 1
- 101710093908 Outer capsid protein VP4 Proteins 0.000 description 1
- 101710135467 Outer capsid protein sigma-1 Proteins 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 101710176177 Protein A56 Proteins 0.000 description 1
- 102100038239 Protein Churchill Human genes 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- KFJCNKPBEPCAJR-UHFFFAOYSA-N S(=O)(=O)(C)OCCN(P1(OCCCN1CCOS(=O)(=O)C)=O)CCOS(=O)(=O)C Chemical compound S(=O)(=O)(C)OCCN(P1(OCCCN1CCOS(=O)(=O)C)=O)CCOS(=O)(=O)C KFJCNKPBEPCAJR-UHFFFAOYSA-N 0.000 description 1
- LXRZVMYMQHNYJB-UNXOBOICSA-N [(1R,2S,4R)-4-[[5-[4-[(1R)-7-chloro-1,2,3,4-tetrahydroisoquinolin-1-yl]-5-methylthiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound CC1=C(C=C(S1)C(=O)C1=C(N[C@H]2C[C@H](O)[C@@H](COS(N)(=O)=O)C2)N=CN=C1)[C@@H]1NCCC2=C1C=C(Cl)C=C2 LXRZVMYMQHNYJB-UNXOBOICSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000000908 ammonium hydroxide Substances 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
- 150000007514 bases Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 210000003743 erythrocyte Anatomy 0.000 description 1
- FRYHCSODNHYDPU-UHFFFAOYSA-N ethanesulfonyl chloride Chemical compound CCS(Cl)(=O)=O FRYHCSODNHYDPU-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 210000000744 eyelid Anatomy 0.000 description 1
- 244000144993 groups of animals Species 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 239000000185 hemagglutinin Substances 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- 210000002865 immune cell Anatomy 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- PWQOZRPSDQKNPW-UHFFFAOYSA-N pentane-1-sulfonyl chloride Chemical compound CCCCCS(Cl)(=O)=O PWQOZRPSDQKNPW-UHFFFAOYSA-N 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
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- KPBSJEBFALFJTO-UHFFFAOYSA-N propane-1-sulfonyl chloride Chemical compound CCCS(Cl)(=O)=O KPBSJEBFALFJTO-UHFFFAOYSA-N 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
- 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
- 239000013558 reference substance Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- UMKFEPPTGMDVMI-UHFFFAOYSA-N trofosfamide Chemical compound ClCCN(CCCl)P1(=O)OCCCN1CCCl UMKFEPPTGMDVMI-UHFFFAOYSA-N 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
- C07F9/65844—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
-
- 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
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 (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2107936 | 1971-02-19 | ||
| DE2107936A DE2107936C3 (de) | 1971-02-19 | 1971-02-19 | Alkylsulfonsäureester von 2-Oxo-13,2-oxazaphosphorinanen und diese enthaltende pharmazeutische Präparate |
| DE19722201675 DE2201675A1 (de) | 1972-01-14 | 1972-01-14 | Alkylsulfonsaeureester 1,3,2-oxazaphospha-cyclischer verbindungen, verfahren zu ihrer herstellung und pharmazeutische praeparate |
| DE2201675 | 1972-01-14 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FI56387B FI56387B (fi) | 1979-09-28 |
| FI56387C true FI56387C (fi) | 1980-01-10 |
Family
ID=25760687
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI445/72A FI56387C (fi) | 1971-02-19 | 1972-02-18 | Foerfarande foer framstaellning av alkansulfonsyraestrar av 1,3,2-oxazafosforinfoereningar med immunitetssaenkande verkan |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US3828090A (da) |
| JP (1) | JPS5620317B1 (da) |
| AR (1) | AR195863A1 (da) |
| BE (1) | BE779516A (da) |
| CA (1) | CA957696A (da) |
| CH (3) | CH596231A5 (da) |
| DD (1) | DD94812A5 (da) |
| DK (1) | DK137013C (da) |
| ES (1) | ES399910A1 (da) |
| FI (1) | FI56387C (da) |
| FR (1) | FR2125595B1 (da) |
| HK (1) | HK11477A (da) |
| HU (1) | HU169427B (da) |
| IE (1) | IE36065B1 (da) |
| LU (1) | LU64702A1 (da) |
| MY (1) | MY7700155A (da) |
| NL (1) | NL170287C (da) |
| SE (1) | SE381464B (da) |
| YU (3) | YU38772A (da) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3910982A (en) * | 1971-02-19 | 1975-10-07 | Asta Werke Ag Chem Fab | Alkylsulfonic acid esters of 1,3,2-oxazaphospha-cyclic compounds |
| US4085128A (en) * | 1974-11-20 | 1978-04-18 | Shionogi & Co., Ltd. | Cyclic phosphamide derivatives |
| CN114965770B (zh) * | 2022-05-24 | 2023-03-28 | 江苏海洋大学 | 一种异环磷酰胺原料药中起始物料、杂质d、杂质f的检测方法 |
-
1972
- 1972-01-31 CH CH1183575A patent/CH596231A5/xx not_active IP Right Cessation
- 1972-01-31 CH CH134972A patent/CH581145A5/xx not_active IP Right Cessation
- 1972-01-31 CH CH1183675A patent/CH586230A5/xx not_active IP Right Cessation
- 1972-02-01 LU LU64702D patent/LU64702A1/xx unknown
- 1972-02-07 IE IE147/72A patent/IE36065B1/xx unknown
- 1972-02-10 US US00225273A patent/US3828090A/en not_active Expired - Lifetime
- 1972-02-16 YU YU00387/72A patent/YU38772A/xx unknown
- 1972-02-17 SE SE7201916A patent/SE381464B/xx unknown
- 1972-02-17 DD DD160930A patent/DD94812A5/xx unknown
- 1972-02-18 BE BE779516A patent/BE779516A/xx not_active IP Right Cessation
- 1972-02-18 HU HUAA698A patent/HU169427B/hu unknown
- 1972-02-18 FI FI445/72A patent/FI56387C/fi active
- 1972-02-18 AR AR240595A patent/AR195863A1/es active
- 1972-02-18 NL NLAANVRAGE7202177,A patent/NL170287C/xx not_active IP Right Cessation
- 1972-02-18 CA CA135,044A patent/CA957696A/en not_active Expired
- 1972-02-18 JP JP1655672A patent/JPS5620317B1/ja active Pending
- 1972-02-18 FR FR7205549A patent/FR2125595B1/fr not_active Expired
- 1972-02-18 DK DK76172A patent/DK137013C/da not_active IP Right Cessation
- 1972-02-18 ES ES399910A patent/ES399910A1/es not_active Expired
-
1977
- 1977-03-03 HK HK114/77A patent/HK11477A/xx unknown
- 1977-12-30 MY MY155/77A patent/MY7700155A/xx unknown
-
1978
- 1978-10-12 YU YU2388/78A patent/YU35030B/xx unknown
- 1978-10-12 YU YU2387/78A patent/YU35031B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR2125595B1 (da) | 1975-03-14 |
| LU64702A1 (da) | 1972-06-29 |
| CH581145A5 (da) | 1976-10-29 |
| AR195863A1 (es) | 1973-11-15 |
| AU3891472A (en) | 1973-08-16 |
| HU169427B (da) | 1976-11-28 |
| JPS5620317B1 (da) | 1981-05-13 |
| CA957696A (en) | 1974-11-12 |
| FI56387B (fi) | 1979-09-28 |
| YU238778A (en) | 1979-12-31 |
| NL170287C (nl) | 1982-10-18 |
| DK137013B (da) | 1978-01-02 |
| YU35031B (en) | 1980-06-30 |
| BE779516A (fr) | 1972-06-16 |
| MY7700155A (en) | 1977-12-31 |
| IE36065B1 (en) | 1976-08-04 |
| YU38772A (en) | 1982-02-28 |
| NL7202177A (da) | 1972-08-22 |
| FR2125595A1 (da) | 1972-09-29 |
| YU35030B (en) | 1980-06-30 |
| NL170287B (nl) | 1982-05-17 |
| CH586230A5 (da) | 1977-03-31 |
| IE36065L (en) | 1972-08-19 |
| DK137013C (da) | 1978-06-05 |
| ES399910A1 (es) | 1975-06-16 |
| YU238878A (en) | 1979-12-31 |
| CH596231A5 (da) | 1978-03-15 |
| US3828090A (en) | 1974-08-06 |
| DD94812A5 (da) | 1973-01-05 |
| SE381464B (sv) | 1975-12-08 |
| HK11477A (en) | 1977-03-11 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0092190B1 (en) | Phospholipid derivatives, process for preparation thereof and pharmaceutical composition of the same | |
| ES2607403T3 (es) | Compuestos químicos como intermedios sintéticos | |
| US5273989A (en) | 3,5-disubstituted 2-isoxazolines and isoxazoles, agents containing them and their use | |
| FR2518088A1 (fr) | Nouveaux derives d'aminoacides, et leur application therapeutique | |
| CA2001401A1 (en) | Quaternary amine containing ether or ester lipid derivatives and therapeutic compositions | |
| JPH09512010A (ja) | タキキニン拮抗薬 | |
| WO1996030353A1 (en) | Reversible protease inhibitors | |
| PT2077996E (pt) | Processo de purificação de montelucaste e seus sais de amina | |
| KR20070015535A (ko) | 증식성 질병 치료용 치환 페녹시- 및 페닐티오- 유도체 | |
| NZ536180A (en) | 2,6-quinolinyl and 2,6-naphthyl derivatives, processes for preparing them and their uses as VLA-4 inhibitors | |
| KR20140106750A (ko) | Mogat-2 억제제로서 유용한 벤질 술폰아미드 유도체 | |
| FI56387C (fi) | Foerfarande foer framstaellning av alkansulfonsyraestrar av 1,3,2-oxazafosforinfoereningar med immunitetssaenkande verkan | |
| CZ25597A3 (cs) | Aryloxy- a arylthiopropanolaminové deriváty, použitelné jako ß3-adrenoreceptorové agonisty a antagonisty ß1- a ß2- adrenoreceptorů a farmaceutické prostředky s jejich obsahem | |
| EP0256137A1 (en) | Bis-dioxopiperazine derivatives | |
| JPS59141559A (ja) | ラクタムペプチド及びその製造方法並びに該ペプチドを含有する医薬 | |
| BR112021013515A2 (pt) | Compostos de anandamida | |
| KR890003789B1 (ko) | 옥스아자포스포린 유도체의 염의 제조방법 | |
| NZ206293A (en) | (n-(2-chloroethyl)-n-nitrosoureido)-methyl phosphonic acid derivatives and pharmaceutical compositions | |
| FI77243C (fi) | Foerfarande foer framstaellning av terapeutiskt anvaendbara 4-(3-alkynyloxi-2-hydroxipropyl)piperazin-1- yl-n-fenylacetamidderivat. | |
| KR100297180B1 (ko) | 인지질유도체및이의제조방법 | |
| AU2011280031A1 (en) | Synthesis and use of Kinase inhibitors | |
| PT101010A (pt) | Derivados de fosforo, processo para a sua preparacao e seu uso em medicina | |
| AU608076B2 (en) | Pharmaceuticals, phosphorus-containing 2-osoxazolines and isoxazoles contained therein, and processes for the preparation of these heterocyclic compounds | |
| CA3040677A1 (en) | Phenothiazine derivatives and methods of use thereof | |
| BR112012022349B1 (pt) | Composto, método para tratar uma doença, e, processo |