FI64377C - Foerfarande foer framstaellning av farmakologiskt vaerdefulla hydroxiaminokolvaetefosfonsyraderivat - Google Patents
Foerfarande foer framstaellning av farmakologiskt vaerdefulla hydroxiaminokolvaetefosfonsyraderivat Download PDFInfo
- Publication number
- FI64377C FI64377C FI772280A FI772280A FI64377C FI 64377 C FI64377 C FI 64377C FI 772280 A FI772280 A FI 772280A FI 772280 A FI772280 A FI 772280A FI 64377 C FI64377 C FI 64377C
- Authority
- FI
- Finland
- Prior art keywords
- acid
- mixture
- reduced pressure
- under reduced
- compound
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 90
- 238000002360 preparation method Methods 0.000 title claims description 29
- 230000000144 pharmacologic effect Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 168
- -1 lower alkenoyl Chemical group 0.000 claims description 67
- 150000003839 salts Chemical class 0.000 claims description 51
- 239000002253 acid Substances 0.000 claims description 35
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- 230000003301 hydrolyzing effect Effects 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 125000001589 carboacyl group Chemical group 0.000 claims description 5
- 125000001118 alkylidene group Chemical group 0.000 claims description 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 271
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 186
- 239000000203 mixture Substances 0.000 description 162
- 230000002829 reductive effect Effects 0.000 description 156
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 148
- 239000000243 solution Substances 0.000 description 146
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 100
- 238000003756 stirring Methods 0.000 description 82
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 81
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 81
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 78
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 66
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 64
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 63
- 238000006243 chemical reaction Methods 0.000 description 62
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 54
- 238000001816 cooling Methods 0.000 description 53
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 52
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 48
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 44
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 42
- 238000001914 filtration Methods 0.000 description 40
- 239000011541 reaction mixture Substances 0.000 description 39
- 239000013078 crystal Substances 0.000 description 38
- 239000007864 aqueous solution Substances 0.000 description 36
- 239000002904 solvent Substances 0.000 description 34
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- 239000000706 filtrate Substances 0.000 description 29
- 239000007858 starting material Substances 0.000 description 29
- CRZNAZZXMBDMBS-UHFFFAOYSA-N 3-(hydroxyamino)propylphosphonic acid Chemical compound ONCCCP(O)(O)=O CRZNAZZXMBDMBS-UHFFFAOYSA-N 0.000 description 28
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 28
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 28
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 27
- 235000019253 formic acid Nutrition 0.000 description 27
- 239000003795 chemical substances by application Substances 0.000 description 25
- 239000002244 precipitate Substances 0.000 description 25
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 24
- 230000007062 hydrolysis Effects 0.000 description 24
- 238000006460 hydrolysis reaction Methods 0.000 description 24
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 239000003921 oil Substances 0.000 description 21
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 20
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 18
- 239000007788 liquid Substances 0.000 description 16
- 239000000843 powder Substances 0.000 description 15
- 238000010992 reflux Methods 0.000 description 15
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 14
- 238000010908 decantation Methods 0.000 description 14
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 14
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 14
- 235000019341 magnesium sulphate Nutrition 0.000 description 14
- 150000007524 organic acids Chemical class 0.000 description 14
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 14
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 14
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 12
- 125000002252 acyl group Chemical group 0.000 description 12
- 238000010438 heat treatment Methods 0.000 description 12
- 150000007529 inorganic bases Chemical class 0.000 description 12
- 150000007530 organic bases Chemical class 0.000 description 12
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 11
- 241000699670 Mus sp. Species 0.000 description 11
- 150000002148 esters Chemical class 0.000 description 11
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 11
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 10
- 235000017557 sodium bicarbonate Nutrition 0.000 description 10
- 238000012360 testing method Methods 0.000 description 10
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 10
- 239000007795 chemical reaction product Substances 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 230000006181 N-acylation Effects 0.000 description 8
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 8
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 8
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 8
- 239000004480 active ingredient Substances 0.000 description 8
- 238000005917 acylation reaction Methods 0.000 description 8
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 8
- 239000002585 base Substances 0.000 description 8
- IYYIVELXUANFED-UHFFFAOYSA-N bromo(trimethyl)silane Chemical compound C[Si](C)(C)Br IYYIVELXUANFED-UHFFFAOYSA-N 0.000 description 8
- GJXWDTUCERCKIX-UHFFFAOYSA-N fosmidomycin Chemical compound O=CN(O)CCCP(O)(O)=O GJXWDTUCERCKIX-UHFFFAOYSA-N 0.000 description 8
- 150000007522 mineralic acids Chemical class 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
- 238000005406 washing Methods 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 229910052783 alkali metal Inorganic materials 0.000 description 7
- 230000026030 halogenation Effects 0.000 description 7
- 238000005658 halogenation reaction Methods 0.000 description 7
- 238000002347 injection Methods 0.000 description 7
- 239000007924 injection Substances 0.000 description 7
- 229920006395 saturated elastomer Polymers 0.000 description 7
- 239000011780 sodium chloride Substances 0.000 description 7
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 6
- 241000588724 Escherichia coli Species 0.000 description 6
- PKMNDDZSIHLLLI-UHFFFAOYSA-N FR900098 Natural products CC(=O)N(O)CCCP(O)(O)=O PKMNDDZSIHLLLI-UHFFFAOYSA-N 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 6
- 125000003710 aryl alkyl group Chemical group 0.000 description 6
- 229920001429 chelating resin Polymers 0.000 description 6
- 238000001103 continuous-wave nuclear magnetic resonance spectrum Methods 0.000 description 6
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 230000002140 halogenating effect Effects 0.000 description 6
- 239000012452 mother liquor Substances 0.000 description 6
- 125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 description 6
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- 241000894006 Bacteria Species 0.000 description 5
- PEIKTSJIUKYDPC-UHFFFAOYSA-N Diethyl 3-Bromopropylphosphonate Chemical compound CCOP(=O)(OCC)CCCBr PEIKTSJIUKYDPC-UHFFFAOYSA-N 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 5
- 241000699666 Mus <mouse, genus> Species 0.000 description 5
- 150000008065 acid anhydrides Chemical class 0.000 description 5
- 230000010933 acylation Effects 0.000 description 5
- 239000003513 alkali Substances 0.000 description 5
- 230000000845 anti-microbial effect Effects 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000006664 bond formation reaction Methods 0.000 description 5
- 238000006704 dehydrohalogenation reaction Methods 0.000 description 5
- 125000000524 functional group Chemical group 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- NSETWVJZUWGCKE-UHFFFAOYSA-N propylphosphonic acid Chemical compound CCCP(O)(O)=O NSETWVJZUWGCKE-UHFFFAOYSA-N 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- ZZPUYRHMTGOTEU-UHFFFAOYSA-M sodium;3-[formyl(hydroxy)amino]propyl-hydroxyphosphinate Chemical compound [Na+].O=CN(O)CCCP(O)([O-])=O ZZPUYRHMTGOTEU-UHFFFAOYSA-M 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 5
- 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 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 4
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
- 241000588770 Proteus mirabilis Species 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 4
- HSFPUYYGGRYBCD-HNQUOIGGSA-N [(e)-3-(hydroxyamino)prop-1-enyl]phosphonic acid Chemical compound ONC\C=C\P(O)(O)=O HSFPUYYGGRYBCD-HNQUOIGGSA-N 0.000 description 4
- GRGAPWQSBFOAEB-UHFFFAOYSA-N [2-hydroxy-3-(hydroxyamino)propyl]phosphonic acid Chemical compound ONCC(O)CP(O)(O)=O GRGAPWQSBFOAEB-UHFFFAOYSA-N 0.000 description 4
- 238000000862 absorption spectrum Methods 0.000 description 4
- 150000001340 alkali metals Chemical class 0.000 description 4
- 238000010171 animal model Methods 0.000 description 4
- 239000003957 anion exchange resin Substances 0.000 description 4
- 244000052616 bacterial pathogen Species 0.000 description 4
- 159000000007 calcium salts Chemical class 0.000 description 4
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- 238000004440 column chromatography Methods 0.000 description 4
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- 150000004820 halides Chemical class 0.000 description 4
- 125000002349 hydroxyamino group Chemical group [H]ON([H])[*] 0.000 description 4
- 208000015181 infectious disease Diseases 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- 239000002198 insoluble material Substances 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
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- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 4
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- 229910000104 sodium hydride Inorganic materials 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 4
- LCFXFDGYDKNWMD-UHFFFAOYSA-M sodium;3-[acetyl(hydroxy)amino]propyl-hydroxyphosphinate Chemical compound [Na+].CC(=O)N(O)CCCP(O)([O-])=O LCFXFDGYDKNWMD-UHFFFAOYSA-M 0.000 description 4
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 4
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 4
- YTQMZWCJYREOLX-FNORWQNLSA-N (e)-3-bromo-1-diethoxyphosphorylprop-1-ene Chemical compound CCOP(=O)(OCC)\C=C\CBr YTQMZWCJYREOLX-FNORWQNLSA-N 0.000 description 3
- NFDYKBILOZTPSH-UHFFFAOYSA-N 1,2-dibromo-3-diethoxyphosphorylpropane Chemical compound CCOP(=O)(OCC)CC(Br)CBr NFDYKBILOZTPSH-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- FUKXIMRHLZJUCG-UHFFFAOYSA-N 2-(diethoxyphosphorylmethyl)oxirane Chemical compound CCOP(=O)(OCC)CC1CO1 FUKXIMRHLZJUCG-UHFFFAOYSA-N 0.000 description 3
- SGLNGTWMRAHPGP-UHFFFAOYSA-N 2-(hydroxyamino)ethylphosphonic acid Chemical compound ONCCP(O)(O)=O SGLNGTWMRAHPGP-UHFFFAOYSA-N 0.000 description 3
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- 241000193830 Bacillus <bacterium> Species 0.000 description 3
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- 241000607762 Shigella flexneri Species 0.000 description 3
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 3
- 241000191967 Staphylococcus aureus Species 0.000 description 3
- ZPNKMADWQYTQCA-FNORWQNLSA-N [(e)-3-[ethoxycarbonyl(ethoxycarbonyloxy)amino]prop-1-enyl]phosphonic acid Chemical compound CCOC(=O)ON(C(=O)OCC)C\C=C\P(O)(O)=O ZPNKMADWQYTQCA-FNORWQNLSA-N 0.000 description 3
- LYOMUCXUUKSHPX-UHFFFAOYSA-N [3-[formyl(hydroxy)amino]-2-hydroxypropyl]phosphonic acid Chemical compound OP(=O)(O)CC(O)CN(O)C=O LYOMUCXUUKSHPX-UHFFFAOYSA-N 0.000 description 3
- 239000008272 agar Substances 0.000 description 3
- 150000001342 alkaline earth metals Chemical class 0.000 description 3
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- 239000012435 aralkylating agent Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 229910052791 calcium Inorganic materials 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 3
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- 239000000391 magnesium silicate Substances 0.000 description 1
- 229940099273 magnesium trisilicate Drugs 0.000 description 1
- 229910000386 magnesium trisilicate Inorganic materials 0.000 description 1
- 235000019793 magnesium trisilicate Nutrition 0.000 description 1
- CRGZYKWWYNQGEC-UHFFFAOYSA-N magnesium;methanolate Chemical compound [Mg+2].[O-]C.[O-]C CRGZYKWWYNQGEC-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- LVWZTYCIRDMTEY-UHFFFAOYSA-N metamizole Chemical compound O=C1C(N(CS(O)(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 LVWZTYCIRDMTEY-UHFFFAOYSA-N 0.000 description 1
- YKPFMADHGKNDFC-UHFFFAOYSA-N methyl n-(3-diethoxyphosphorylpropyl)-n-methoxycarbamate Chemical compound CCOP(=O)(OCC)CCCN(OC)C(=O)OC YKPFMADHGKNDFC-UHFFFAOYSA-N 0.000 description 1
- 244000000010 microbial pathogen Species 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- UHAAFJWANJYDIS-UHFFFAOYSA-N n,n'-diethylmethanediimine Chemical compound CCN=C=NCC UHAAFJWANJYDIS-UHFFFAOYSA-N 0.000 description 1
- NICSJKGTHKHXHJ-UHFFFAOYSA-N n-(2-diethoxyphosphorylethyl)-4-methyl-n-phenylmethoxybenzenesulfonamide Chemical compound C=1C=C(C)C=CC=1S(=O)(=O)N(CCP(=O)(OCC)OCC)OCC1=CC=CC=C1 NICSJKGTHKHXHJ-UHFFFAOYSA-N 0.000 description 1
- FIIAURDOOMZDSO-UHFFFAOYSA-N n-(3-dibutoxyphosphorylpropyl)-n-[(4-methoxyphenyl)methoxy]-4-methylbenzenesulfonamide Chemical compound C=1C=C(C)C=CC=1S(=O)(=O)N(CCCP(=O)(OCCCC)OCCCC)OCC1=CC=C(OC)C=C1 FIIAURDOOMZDSO-UHFFFAOYSA-N 0.000 description 1
- HDBTXCARFLUKHW-UHFFFAOYSA-N n-(3-diethoxyphosphorylpropyl)-4-methyl-n-phenylmethoxybenzenesulfonamide Chemical compound C=1C=C(C)C=CC=1S(=O)(=O)N(CCCP(=O)(OCC)OCC)OCC1=CC=CC=C1 HDBTXCARFLUKHW-UHFFFAOYSA-N 0.000 description 1
- YJZRNHAEJAYEAH-UHFFFAOYSA-N n-(3-diethoxyphosphorylpropyl)-n-hydroxyformamide Chemical compound CCOP(=O)(OCC)CCCN(O)C=O YJZRNHAEJAYEAH-UHFFFAOYSA-N 0.000 description 1
- JVHPKYBRJQNPAT-UHFFFAOYSA-N n-cyclohexyl-2,2-diphenylethenimine Chemical compound C1CCCCC1N=C=C(C=1C=CC=CC=1)C1=CC=CC=C1 JVHPKYBRJQNPAT-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- MVSMBIBGGPSEHQ-UHFFFAOYSA-N o-[(4-methoxyphenyl)methyl]hydroxylamine Chemical compound COC1=CC=C(CON)C=C1 MVSMBIBGGPSEHQ-UHFFFAOYSA-N 0.000 description 1
- 239000012053 oil suspension Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- USHDBZLNUZHGOP-UHFFFAOYSA-N pentyl hypochlorite Chemical compound CCCCCOCl USHDBZLNUZHGOP-UHFFFAOYSA-N 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- CMPQUABWPXYYSH-UHFFFAOYSA-N phenyl phosphate Chemical compound OP(O)(=O)OC1=CC=CC=C1 CMPQUABWPXYYSH-UHFFFAOYSA-N 0.000 description 1
- 229910000065 phosphene Inorganic materials 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 229910001392 phosphorus oxide Inorganic materials 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- RLEHFYQHNYDXPO-UHFFFAOYSA-M potassium 3-[formyl(hydroxy)amino]propyl-hydroxyphosphinate Chemical compound [K+].C(=O)N(O)CCCP([O-])(O)=O RLEHFYQHNYDXPO-UHFFFAOYSA-M 0.000 description 1
- BDVCDIIOVZUEQA-UHFFFAOYSA-M potassium [3-[formyl(hydroxy)amino]-2-methylpropyl]-hydroxyphosphinate Chemical compound [K+].C(=O)N(O)CC(CP([O-])(O)=O)C BDVCDIIOVZUEQA-UHFFFAOYSA-M 0.000 description 1
- 229940050271 potassium alum Drugs 0.000 description 1
- GRLPQNLYRHEGIJ-UHFFFAOYSA-J potassium aluminium sulfate Chemical compound [Al+3].[K+].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O GRLPQNLYRHEGIJ-UHFFFAOYSA-J 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- XWCIXXXLOAAWPU-UHFFFAOYSA-N prop-1-enylphosphonic acid Chemical compound CC=CP(O)(O)=O XWCIXXXLOAAWPU-UHFFFAOYSA-N 0.000 description 1
- 229940054344 proteus inconstans Drugs 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- VFIZBHJTOHUOEK-UHFFFAOYSA-N s-ethylisothiourea Chemical compound CCSC(N)=N VFIZBHJTOHUOEK-UHFFFAOYSA-N 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- IWNHLFUMKRAZQA-UHFFFAOYSA-M sodium hydroxy(propyl)phosphinate Chemical compound [Na+].CCCP(O)([O-])=O IWNHLFUMKRAZQA-UHFFFAOYSA-M 0.000 description 1
- UHLZJEICLZEUGM-UHFFFAOYSA-M sodium hydroxy-[3-[hydroxy-(2-hydroxyacetyl)amino]propyl]phosphinate Chemical compound [Na+].OCC(=O)N(O)CCCP([O-])(O)=O UHLZJEICLZEUGM-UHFFFAOYSA-M 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- PCAPQADOOHVDEL-UHFFFAOYSA-M sodium;2-[acetyl(hydroxy)amino]ethyl-hydroxyphosphinate Chemical compound [Na+].CC(=O)N(O)CCP(O)([O-])=O PCAPQADOOHVDEL-UHFFFAOYSA-M 0.000 description 1
- CFUCDMRKUNLBRQ-UHFFFAOYSA-M sodium;n,n-diethylethanamine;hydrogen carbonate Chemical compound [Na+].OC([O-])=O.CCN(CC)CC CFUCDMRKUNLBRQ-UHFFFAOYSA-M 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 239000007916 tablet composition Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- IXZDIALLLMRYOU-UHFFFAOYSA-N tert-butyl hypochlorite Chemical compound CC(C)(C)OCl IXZDIALLLMRYOU-UHFFFAOYSA-N 0.000 description 1
- NYBWUHOMYZZKOR-UHFFFAOYSA-N tes-adt Chemical class C1=C2C(C#C[Si](CC)(CC)CC)=C(C=C3C(SC=C3)=C3)C3=C(C#C[Si](CC)(CC)CC)C2=CC2=C1SC=C2 NYBWUHOMYZZKOR-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 1
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 1
- VSAISIQCTGDGPU-UHFFFAOYSA-N tetraphosphorus hexaoxide Chemical compound O1P(O2)OP3OP1OP2O3 VSAISIQCTGDGPU-UHFFFAOYSA-N 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 150000003560 thiocarbamic acids Chemical class 0.000 description 1
- 150000003566 thiocarboxylic acids Chemical class 0.000 description 1
- DHCDFWKWKRSZHF-UHFFFAOYSA-L thiosulfate(2-) Chemical compound [O-]S([S-])(=O)=O DHCDFWKWKRSZHF-UHFFFAOYSA-L 0.000 description 1
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- SDRXUONWFFNMIJ-UHFFFAOYSA-N triazatriphosphinine Chemical compound n1npppn1 SDRXUONWFFNMIJ-UHFFFAOYSA-N 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 description 1
- 229940099259 vaseline Drugs 0.000 description 1
- 239000001993 wax 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
- C07F9/3808—Acyclic saturated acids which can have further substituents on alkyl
-
- 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
- C07F9/3826—Acyclic unsaturated acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Oncology (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Communicable Diseases (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Cephalosporin Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI821745A FI70594C (fi) | 1976-07-27 | 1982-05-18 | Foerfarande foer framstaellning av farmakologiskt vaerdefulla hydroxiaminkolvaetefosfonsyraderivat |
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3133976 | 1976-07-27 | ||
| GB3133976 | 1976-07-27 | ||
| GB4222276 | 1976-10-11 | ||
| GB4222276 | 1976-10-11 | ||
| GB31339/76A GB1580899A (en) | 1976-07-27 | 1977-06-20 | Hydroxyaminohydrocarbonphosphonic acid derivatives and production and use thereof |
| GB2570077 | 1977-06-20 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI772280A FI772280A (da) | 1978-01-28 |
| FI64377B FI64377B (fi) | 1983-07-29 |
| FI64377C true FI64377C (fi) | 1983-11-10 |
Family
ID=27258468
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI772280A FI64377C (fi) | 1976-07-27 | 1977-07-26 | Foerfarande foer framstaellning av farmakologiskt vaerdefulla hydroxiaminokolvaetefosfonsyraderivat |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US4182758A (da) |
| JP (1) | JPS5340720A (da) |
| AR (1) | AR226522A1 (da) |
| AT (2) | AT367064B (da) |
| CA (1) | CA1091241A (da) |
| CH (5) | CH640862A5 (da) |
| DE (2) | DE2733658A1 (da) |
| DK (1) | DK149609C (da) |
| ES (3) | ES461084A1 (da) |
| FI (1) | FI64377C (da) |
| FR (1) | FR2474505A1 (da) |
| GB (1) | GB1580899A (da) |
| GR (1) | GR61140B (da) |
| HU (1) | HU182023B (da) |
| IE (1) | IE45536B1 (da) |
| NL (1) | NL7708325A (da) |
| NO (1) | NO157504C (da) |
| OA (1) | OA05725A (da) |
| PH (1) | PH14401A (da) |
| PT (1) | PT66854B (da) |
| SE (1) | SE441360B (da) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4084953A (en) * | 1977-03-09 | 1978-04-18 | Monsanto Company | N-hydroxy-N-phosphonomethylglycines and the herbicidal use thereof |
| US4210635A (en) * | 1978-02-15 | 1980-07-01 | Fujisawa Pharmaceutical Co., Ltd. | Antibacterial composition |
| US4268503A (en) * | 1978-09-14 | 1981-05-19 | Fujisawa Pharmaceutical Co., Ltd. | Antibacterial composition |
| US4693742A (en) * | 1983-12-20 | 1987-09-15 | Rohm And Hass Company | Herbicidal hydroxyamino phosphonic acids and derivatives |
| US5189030A (en) * | 1985-06-11 | 1993-02-23 | Ciba-Geigy Corporation | 1-amino-2-phenylethanephosphonic acids as microbiocides |
| JPH0340299U (da) * | 1989-08-31 | 1991-04-18 | ||
| DE19825585A1 (de) * | 1998-04-14 | 1999-10-21 | Hassan Jomaa | Verwendung von Aminohydrocarbylphosphonsäurederivaten zur therapeutischen und prophylaktischen Behandlung von Infektionen, die durch Parasiten, Pilze oder Viren hervorgerufen werden |
| TR200002965T2 (tr) | 1998-04-14 | 2001-05-21 | Jomaa,Hassan | Enfeksiyonların terapötik ve profilaktik tedavisi için organofosforlu terkiplerin kullanımı |
| DE19843223A1 (de) * | 1998-09-22 | 2000-03-30 | Hassan Jomaa | Phosphororganische Verbindungen und ihre Verwendung |
| US6753324B2 (en) | 1998-07-15 | 2004-06-22 | Hassan Jomaa | Phosphorous organic compounds and their use |
| AP2001002051A0 (en) | 1998-07-15 | 2001-03-31 | Hassan Jomaa | Phosphorous organic compounds and their use. |
| AU5034899A (en) * | 1998-07-15 | 2000-02-07 | Jomaa Hassan | Drugs containing phosphoric acid derivatives as active ingredient and their use |
| DE19854403A1 (de) * | 1998-11-25 | 2000-05-31 | Hassan Jomaa | Phosphororganische Verbindungen und ihre Verwendung |
| WO2001060829A1 (de) * | 2000-02-18 | 2001-08-23 | Jomaa Pharmaka Gmbh | Phosphororganische verbindungen und ihre verwendung |
| DE10035189A1 (de) * | 2000-07-20 | 2002-02-21 | Hassan Jomaa | Arzneimittel zur oralen Applikation mit einem Gehalt an 3-N-Formylhydroxylaminopropylphosphonsäureestern oder 3-N-Acetylhydroxylaminopropylphosphonsäureestern als Wirkstoff |
| US20080300222A1 (en) * | 2005-10-06 | 2008-12-04 | Innate Pharma | Phosphoantigen Salts Of Organic Bases And Methods For Their Crystallization |
| WO2007088878A1 (ja) * | 2006-01-31 | 2007-08-09 | Api Corporation | ベンゾアゼピノン類の製造方法 |
| AU2009276343A1 (en) | 2008-08-01 | 2010-02-04 | Bioxiness Pharmaceuticals, Inc. | Methionine analogs and methods of using same |
| EP2404601A1 (en) | 2010-07-06 | 2012-01-11 | BioAgency AG | New drug combinations for the treatment of Malaria |
| EP2725029A1 (en) * | 2012-10-29 | 2014-04-30 | Laboratoire Biodim | New antibacterial compounds and biological applications thereof |
| WO2019246119A1 (en) * | 2018-06-18 | 2019-12-26 | The George Washington University a Congressionally Chartered Not-for-Profit Corporation | Antibiotics for veterinary staphylococcal infections |
| EP4045056A1 (de) | 2019-10-19 | 2022-08-24 | DMG Deutsche Malaria GmbH | Kombinationspräparate von 3-n-formylhydroxylaminopropylphosphonsäurederivaten oder 3-n-acetylhydroxylaminopropylphosphonsäurederivaten mit clindamycin und artesunat |
| EP3960176A1 (en) | 2020-08-26 | 2022-03-02 | DMG Deutsche Malaria GmbH | Piperaquine and related drug combinations for use in the treatment of covid-19 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL6905272A (da) | 1968-05-15 | 1969-11-18 | ||
| US3764677A (en) * | 1971-06-25 | 1973-10-09 | Gates Rubber Co | Diethyl betaaminoethylphosphonate as an antimicrobial agent |
-
1977
- 1977-06-20 GB GB31339/76A patent/GB1580899A/en not_active Expired
- 1977-07-25 PH PH20031A patent/PH14401A/en unknown
- 1977-07-25 HU HU77FU356A patent/HU182023B/hu not_active IP Right Cessation
- 1977-07-26 DE DE19772733658 patent/DE2733658A1/de active Granted
- 1977-07-26 IE IE1555/77A patent/IE45536B1/en unknown
- 1977-07-26 SE SE7708592A patent/SE441360B/xx not_active IP Right Cessation
- 1977-07-26 DE DE2760320A patent/DE2760320C2/de not_active Expired
- 1977-07-26 FI FI772280A patent/FI64377C/fi not_active IP Right Cessation
- 1977-07-26 DK DK337877A patent/DK149609C/da not_active IP Right Cessation
- 1977-07-26 NO NO772652A patent/NO157504C/no unknown
- 1977-07-26 CA CA283,566A patent/CA1091241A/en not_active Expired
- 1977-07-26 GR GR54041A patent/GR61140B/el unknown
- 1977-07-27 CH CH930777A patent/CH640862A5/de not_active IP Right Cessation
- 1977-07-27 US US05/819,554 patent/US4182758A/en not_active Expired - Lifetime
- 1977-07-27 JP JP9081077A patent/JPS5340720A/ja active Granted
- 1977-07-27 AR AR268576A patent/AR226522A1/es active
- 1977-07-27 NL NL7708325A patent/NL7708325A/xx not_active Application Discontinuation
- 1977-07-27 OA OA56240A patent/OA05725A/xx unknown
- 1977-07-27 ES ES461084A patent/ES461084A1/es not_active Expired
- 1977-07-27 FR FR7723128A patent/FR2474505A1/fr active Granted
- 1977-07-27 AT AT0550977A patent/AT367064B/de not_active IP Right Cessation
- 1977-07-27 PT PT66854A patent/PT66854B/pt unknown
-
1978
- 1978-07-17 ES ES471822A patent/ES471822A1/es not_active Expired
-
1979
- 1979-04-02 ES ES479211A patent/ES479211A1/es not_active Expired
- 1979-08-22 AT AT0564879A patent/AT367430B/de not_active IP Right Cessation
-
1984
- 1984-01-31 CH CH42684A patent/CH646980A5/de not_active IP Right Cessation
- 1984-01-31 CH CH42584A patent/CH646979A5/de not_active IP Right Cessation
- 1984-01-31 CH CH42484A patent/CH646978A5/de not_active IP Right Cessation
- 1984-01-31 CH CH427/84A patent/CH647807A5/de not_active IP Right Cessation
Also Published As
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Owner name: FUJISAWA PHARMACEUTICAL CO. LTD. |