AU2462397A - Use of phosphonic acid esters for the treatment of functional disorder s of the brain and depression - Google Patents
Use of phosphonic acid esters for the treatment of functional disorder s of the brain and depressionInfo
- Publication number
- AU2462397A AU2462397A AU24623/97A AU2462397A AU2462397A AU 2462397 A AU2462397 A AU 2462397A AU 24623/97 A AU24623/97 A AU 24623/97A AU 2462397 A AU2462397 A AU 2462397A AU 2462397 A AU2462397 A AU 2462397A
- Authority
- AU
- Australia
- Prior art keywords
- dimethyl
- phosphonate
- trichloroethane
- thiophosphonate
- trifluoroethane
- 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.)
- Abandoned
Links
- 150000003008 phosphonic acid esters Chemical class 0.000 title claims description 11
- 210000004556 brain Anatomy 0.000 title claims description 9
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 115
- -1 1,1-dichloroethyl Chemical group 0.000 claims description 40
- 150000001875 compounds Chemical class 0.000 claims description 37
- 125000000217 alkyl group Chemical group 0.000 claims description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- 239000001257 hydrogen Substances 0.000 claims description 24
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 16
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 13
- 229910052760 oxygen Inorganic materials 0.000 claims description 13
- 239000001301 oxygen Substances 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 10
- 230000002265 prevention Effects 0.000 claims description 10
- 230000008569 process Effects 0.000 claims description 9
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 8
- 125000004673 propylcarbonyl group Chemical group 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 239000005864 Sulphur Chemical group 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 6
- 150000001340 alkali metals Chemical class 0.000 claims description 6
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 6
- 230000001225 therapeutic effect Effects 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Natural products CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
- 239000011230 binding agent Substances 0.000 claims description 4
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 claims description 4
- 238000009472 formulation Methods 0.000 claims description 4
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims description 4
- JJWOJYKPBOIHIH-UHFFFAOYSA-N P(O)(O)=O.CC(C(C)(C)C)(O)C Chemical compound P(O)(O)=O.CC(C(C)(C)C)(O)C JJWOJYKPBOIHIH-UHFFFAOYSA-N 0.000 claims description 3
- GRLKOVOHJVMDGP-UHFFFAOYSA-N P(O)(O)=S.CC(C(Cl)(Cl)Cl)(OS(=O)(=O)C)C Chemical compound P(O)(O)=S.CC(C(Cl)(Cl)Cl)(OS(=O)(=O)C)C GRLKOVOHJVMDGP-UHFFFAOYSA-N 0.000 claims description 3
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims description 3
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims description 3
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 3
- 150000002366 halogen compounds Chemical class 0.000 claims description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 3
- 239000011707 mineral Substances 0.000 claims description 3
- KZHGNHTVCUWRKR-UHFFFAOYSA-N 1-dimethoxyphosphorylethanol Chemical compound COP(=O)(OC)C(C)O KZHGNHTVCUWRKR-UHFFFAOYSA-N 0.000 claims description 2
- KPWDGTGXUYRARH-UHFFFAOYSA-N 2,2,2-trichloroethanol Chemical compound OCC(Cl)(Cl)Cl KPWDGTGXUYRARH-UHFFFAOYSA-N 0.000 claims description 2
- WCTWNULOJPCSCT-UHFFFAOYSA-N P(O)(O)=O.CC(C(C)(Cl)Cl)(O)C Chemical compound P(O)(O)=O.CC(C(C)(Cl)Cl)(O)C WCTWNULOJPCSCT-UHFFFAOYSA-N 0.000 claims description 2
- NVCISMLILWNMIY-UHFFFAOYSA-N P(O)(O)=O.CC(C(CCl)(Cl)Cl)(O)C Chemical compound P(O)(O)=O.CC(C(CCl)(Cl)Cl)(O)C NVCISMLILWNMIY-UHFFFAOYSA-N 0.000 claims description 2
- RWPXVKPHOFPVFL-UHFFFAOYSA-N P(O)(O)=O.CC(C(Cl)(Cl)Cl)(OC(=O)OC)C Chemical compound P(O)(O)=O.CC(C(Cl)(Cl)Cl)(OC(=O)OC)C RWPXVKPHOFPVFL-UHFFFAOYSA-N 0.000 claims description 2
- ABZUXMLOTWSNBI-UHFFFAOYSA-N P(O)(O)=O.CC(C(Cl)(Cl)Cl)(OC(C)=O)C Chemical compound P(O)(O)=O.CC(C(Cl)(Cl)Cl)(OC(C)=O)C ABZUXMLOTWSNBI-UHFFFAOYSA-N 0.000 claims description 2
- SGNWGVAXMNLLKS-UHFFFAOYSA-N P(O)(O)=O.CC(C(Cl)(Cl)Cl)(OS(=O)(=O)CC)C Chemical compound P(O)(O)=O.CC(C(Cl)(Cl)Cl)(OS(=O)(=O)CC)C SGNWGVAXMNLLKS-UHFFFAOYSA-N 0.000 claims description 2
- SILNJAKRSFWURB-UHFFFAOYSA-N P(O)(O)=O.CC(C(F)(F)F)(OC(=O)CCC)C Chemical compound P(O)(O)=O.CC(C(F)(F)F)(OC(=O)CCC)C SILNJAKRSFWURB-UHFFFAOYSA-N 0.000 claims description 2
- OKRUFOFYLIRAQU-UHFFFAOYSA-N P(O)(O)=O.CC(C(F)(F)F)(OC(=O)N(C)C)C Chemical compound P(O)(O)=O.CC(C(F)(F)F)(OC(=O)N(C)C)C OKRUFOFYLIRAQU-UHFFFAOYSA-N 0.000 claims description 2
- FBIPUSHEVZRHPX-UHFFFAOYSA-N P(O)(O)=O.CC(C(F)(F)F)(OC(=O)OC)C Chemical compound P(O)(O)=O.CC(C(F)(F)F)(OC(=O)OC)C FBIPUSHEVZRHPX-UHFFFAOYSA-N 0.000 claims description 2
- VPHJFRAIEHBFDC-UHFFFAOYSA-N P(O)(O)=O.CC(C(F)(F)F)(OC(C)=O)C Chemical compound P(O)(O)=O.CC(C(F)(F)F)(OC(C)=O)C VPHJFRAIEHBFDC-UHFFFAOYSA-N 0.000 claims description 2
- FWXRCBFEKSRIQN-UHFFFAOYSA-N P(O)(O)=O.CC(C(F)(F)F)(OS(=O)(=O)C)C Chemical compound P(O)(O)=O.CC(C(F)(F)F)(OS(=O)(=O)C)C FWXRCBFEKSRIQN-UHFFFAOYSA-N 0.000 claims description 2
- KTQIMUKIUQTDNG-UHFFFAOYSA-N P(O)(O)=O.CCC(C)(O)C Chemical compound P(O)(O)=O.CCC(C)(O)C KTQIMUKIUQTDNG-UHFFFAOYSA-N 0.000 claims description 2
- ZDJKMWWTHWTJAC-UHFFFAOYSA-N P(O)(O)=S.CC(C(Cl)(Cl)Cl)(OC(=O)OC)C.P(O)(O)=S.CC(C(Cl)(Cl)Cl)(OC(C)=O)C Chemical compound P(O)(O)=S.CC(C(Cl)(Cl)Cl)(OC(=O)OC)C.P(O)(O)=S.CC(C(Cl)(Cl)Cl)(OC(C)=O)C ZDJKMWWTHWTJAC-UHFFFAOYSA-N 0.000 claims description 2
- CQHXZPDHVTZZSI-UHFFFAOYSA-N P(O)(O)=S.CC(C(Cl)(Cl)Cl)(OC(=O)OCC)C Chemical compound P(O)(O)=S.CC(C(Cl)(Cl)Cl)(OC(=O)OCC)C CQHXZPDHVTZZSI-UHFFFAOYSA-N 0.000 claims description 2
- 150000003863 ammonium salts Chemical class 0.000 claims description 2
- 230000003197 catalytic effect Effects 0.000 claims description 2
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 2
- 125000004672 ethylcarbonyl group Chemical group [H]C([H])([H])C([H])([H])C(*)=O 0.000 claims description 2
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 2
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims description 2
- 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 claims description 2
- 229910017464 nitrogen compound Inorganic materials 0.000 claims description 2
- 150000002830 nitrogen compounds Chemical class 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000004742 propyloxycarbonyl group Chemical group 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- AUVHTTJUUPZVOA-UHFFFAOYSA-N P(O)(O)=O.CC(C(Cl)(Cl)Cl)(OC(=O)CC)C Chemical compound P(O)(O)=O.CC(C(Cl)(Cl)Cl)(OC(=O)CC)C AUVHTTJUUPZVOA-UHFFFAOYSA-N 0.000 claims 1
- AYFSGFUIUSPJGB-UHFFFAOYSA-N P(O)(O)=O.CS(=O)(=O)OCC(Cl)(Cl)Cl Chemical compound P(O)(O)=O.CS(=O)(=O)OCC(Cl)(Cl)Cl AYFSGFUIUSPJGB-UHFFFAOYSA-N 0.000 claims 1
- MTBHDLCCFIRCBE-UHFFFAOYSA-N P(O)(O)=S.CC(C(F)(F)F)(O)C.P(O)(O)=S.CC(C(Cl)(Cl)Cl)(OC(=O)N(C)C)C Chemical compound P(O)(O)=S.CC(C(F)(F)F)(O)C.P(O)(O)=S.CC(C(Cl)(Cl)Cl)(OC(=O)N(C)C)C MTBHDLCCFIRCBE-UHFFFAOYSA-N 0.000 claims 1
- RHQDFWAXVIIEBN-UHFFFAOYSA-N Trifluoroethanol Chemical compound OCC(F)(F)F RHQDFWAXVIIEBN-UHFFFAOYSA-N 0.000 claims 1
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims 1
- 238000012360 testing method Methods 0.000 description 23
- 241001465754 Metazoa Species 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 241000700159 Rattus Species 0.000 description 10
- 230000000694 effects Effects 0.000 description 9
- 238000012549 training Methods 0.000 description 9
- 241000699670 Mus sp. Species 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 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 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- 206010012289 Dementia Diseases 0.000 description 5
- 239000003085 diluting agent Substances 0.000 description 5
- 208000035475 disorder Diseases 0.000 description 5
- 208000024827 Alzheimer disease Diseases 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- 230000003542 behavioural effect Effects 0.000 description 4
- 208000010877 cognitive disease Diseases 0.000 description 4
- 229960001952 metrifonate Drugs 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 description 4
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 3
- KNCHDRLWPAKSII-UHFFFAOYSA-N 4-ethyl-2-methylpyridine Chemical group CCC1=CC=NC(C)=C1 KNCHDRLWPAKSII-UHFFFAOYSA-N 0.000 description 3
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 102000003914 Cholinesterases Human genes 0.000 description 3
- 108090000322 Cholinesterases Proteins 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 208000019022 Mood disease Diseases 0.000 description 3
- 241000699666 Mus <mouse, genus> Species 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- FNVWJISAIMKCJI-UHFFFAOYSA-N P(O)(O)=O.CC(C(Cl)(Cl)Cl)(O)C Chemical compound P(O)(O)=O.CC(C(Cl)(Cl)Cl)(O)C FNVWJISAIMKCJI-UHFFFAOYSA-N 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 230000006399 behavior Effects 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- 229940048961 cholinesterase Drugs 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000000546 pharmaceutical excipient Substances 0.000 description 3
- 229960003975 potassium Drugs 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 239000001117 sulphuric acid Substances 0.000 description 3
- 235000011149 sulphuric acid Nutrition 0.000 description 3
- 230000009182 swimming Effects 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- 206010061285 Mental disorder due to a general medical condition Diseases 0.000 description 2
- 208000005314 Multi-Infarct Dementia Diseases 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 206010036631 Presenile dementia Diseases 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 201000004810 Vascular dementia Diseases 0.000 description 2
- 239000000370 acceptor Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000000935 antidepressant agent Substances 0.000 description 2
- 229940005513 antidepressants Drugs 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 230000001149 cognitive effect Effects 0.000 description 2
- 230000001143 conditioned effect Effects 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- OEBRKCOSUFCWJD-UHFFFAOYSA-N dichlorvos Chemical compound COP(=O)(OC)OC=C(Cl)Cl OEBRKCOSUFCWJD-UHFFFAOYSA-N 0.000 description 2
- 229950001327 dichlorvos Drugs 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- WMFOQBRAJBCJND-UHFFFAOYSA-M lithium hydroxide Inorganic materials [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- SGUVLZREKBPKCE-UHFFFAOYSA-N 1,5-diazabicyclo[4.3.0]-non-5-ene Chemical compound C1CCN=C2CCCN21 SGUVLZREKBPKCE-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- FJJYHTVHBVXEEQ-UHFFFAOYSA-N 2,2-dimethylpropanal Chemical compound CC(C)(C)C=O FJJYHTVHBVXEEQ-UHFFFAOYSA-N 0.000 description 1
- PGZVFRAEAAXREB-UHFFFAOYSA-N 2,2-dimethylpropanoyl 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OC(=O)C(C)(C)C PGZVFRAEAAXREB-UHFFFAOYSA-N 0.000 description 1
- CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-UHFFFAOYSA-N 0.000 description 1
- NTSLROIKFLNUIJ-UHFFFAOYSA-N 5-Ethyl-2-methylpyridine Chemical compound CCC1=CC=C(C)N=C1 NTSLROIKFLNUIJ-UHFFFAOYSA-N 0.000 description 1
- 206010065040 AIDS dementia complex Diseases 0.000 description 1
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- 229940122041 Cholinesterase inhibitor Drugs 0.000 description 1
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- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 1
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- XSJNPWZMZZOATI-UHFFFAOYSA-N P(O)(O)=O.CC(C(F)(F)F)(OC(=O)NCCC)C Chemical compound P(O)(O)=O.CC(C(F)(F)F)(OC(=O)NCCC)C XSJNPWZMZZOATI-UHFFFAOYSA-N 0.000 description 1
- FODUIGCUQPKPSV-UHFFFAOYSA-N P(O)(O)=S.CC(C(Cl)(Cl)Cl)(O)C Chemical compound P(O)(O)=S.CC(C(Cl)(Cl)Cl)(O)C FODUIGCUQPKPSV-UHFFFAOYSA-N 0.000 description 1
- KLUXYVWFBFVYLR-UHFFFAOYSA-N P(O)(O)=S.CC(C(Cl)(Cl)Cl)(OC(=O)NCCC)C Chemical compound P(O)(O)=S.CC(C(Cl)(Cl)Cl)(OC(=O)NCCC)C KLUXYVWFBFVYLR-UHFFFAOYSA-N 0.000 description 1
- XGOBVPXEDVHXLM-UHFFFAOYSA-N P(O)(O)=S.CC(C(F)(F)F)(O)C Chemical compound P(O)(O)=S.CC(C(F)(F)F)(O)C XGOBVPXEDVHXLM-UHFFFAOYSA-N 0.000 description 1
- 208000018737 Parkinson disease Diseases 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- PIJVFDBKTWXHHD-UHFFFAOYSA-N Physostigmine Natural products C12=CC(OC(=O)NC)=CC=C2N(C)C2C1(C)CCN2C PIJVFDBKTWXHHD-UHFFFAOYSA-N 0.000 description 1
- 206010039966 Senile dementia Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000000507 anthelmentic effect Effects 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 229950010691 butonate Drugs 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 235000010216 calcium carbonate Nutrition 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000005356 chiral GC Methods 0.000 description 1
- 230000001713 cholinergic effect Effects 0.000 description 1
- 239000000544 cholinesterase inhibitor Substances 0.000 description 1
- 230000007278 cognition impairment Effects 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003412 degenerative effect Effects 0.000 description 1
- 239000012973 diazabicyclooctane Substances 0.000 description 1
- 125000004774 dichlorofluoromethyl group Chemical group FC(Cl)(Cl)* 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- CZHYKKAKFWLGJO-UHFFFAOYSA-N dimethyl phosphite Chemical compound COP([O-])OC CZHYKKAKFWLGJO-UHFFFAOYSA-N 0.000 description 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 1
- 229940113088 dimethylacetamide Drugs 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000012750 in vivo screening Methods 0.000 description 1
- 230000007574 infarction Effects 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000015654 memory Effects 0.000 description 1
- 206010027175 memory impairment Diseases 0.000 description 1
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N methyl iso-propyl ketone Natural products CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 1
- XRKQMIFKHDXFNQ-UHFFFAOYSA-N n-cyclohexyl-n-ethylcyclohexanamine Chemical compound C1CCCCC1N(CC)C1CCCCC1 XRKQMIFKHDXFNQ-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000008177 pharmaceutical agent Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- PIJVFDBKTWXHHD-HIFRSBDPSA-N physostigmine Chemical compound C12=CC(OC(=O)NC)=CC=C2N(C)[C@@H]2[C@@]1(C)CCN2C PIJVFDBKTWXHHD-HIFRSBDPSA-N 0.000 description 1
- 229960001697 physostigmine Drugs 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 235000008476 powdered milk Nutrition 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000013558 reference substance Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 230000006886 spatial memory Effects 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 125000006253 t-butylcarbonyl group Chemical group [H]C([H])([H])C(C(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLJREFDVOIBQDA-UHFFFAOYSA-N tacrine Chemical compound C1=CC=C2C(N)=C(CCCC3)C3=NC2=C1 YLJREFDVOIBQDA-UHFFFAOYSA-N 0.000 description 1
- 229960001685 tacrine Drugs 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/66—Phosphorus compounds
-
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Neurology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Neurosurgery (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Biomedical Technology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Psychiatry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pain & Pain Management (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Epidemiology (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19616471 | 1996-04-25 | ||
| DE19616471A DE19616471A1 (de) | 1996-04-25 | 1996-04-25 | Phosponsäureester zur Behandlung von Hirnleistungsstörungen und Depressionen |
| PCT/US1997/006469 WO1997039756A1 (en) | 1996-04-25 | 1997-04-17 | Use of phosphonic acid esters for the treatment of functional disorders of the brain and depression |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2462397A true AU2462397A (en) | 1997-11-12 |
Family
ID=7792381
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU24623/97A Abandoned AU2462397A (en) | 1996-04-25 | 1997-04-17 | Use of phosphonic acid esters for the treatment of functional disorder s of the brain and depression |
Country Status (19)
| Country | Link |
|---|---|
| EP (1) | EP0896540A1 (id) |
| JP (1) | JP2000510455A (id) |
| KR (1) | KR20000010611A (id) |
| AR (1) | AR006870A1 (id) |
| AU (1) | AU2462397A (id) |
| BG (1) | BG102864A (id) |
| BR (1) | BR9709300A (id) |
| CA (1) | CA2252567A1 (id) |
| CZ (1) | CZ343498A3 (id) |
| DE (1) | DE19616471A1 (id) |
| HU (1) | HUP9903366A3 (id) |
| ID (1) | ID16678A (id) |
| IL (1) | IL126698A0 (id) |
| NO (1) | NO984964L (id) |
| PL (1) | PL333464A1 (id) |
| SK (1) | SK146398A3 (id) |
| TR (1) | TR199802137T2 (id) |
| WO (1) | WO1997039756A1 (id) |
| ZA (1) | ZA973538B (id) |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1078370B (de) * | 1958-09-16 | 1960-03-24 | Norddeutsche Affinerie | Schaedlingsbekaempfungsmittel |
| US3069312A (en) * | 1960-09-28 | 1962-12-18 | California Research Corp | N-substituted dimethyl 1-carbamoyloxy-2, 2, 2-trichloroethyl phosphonates as insecticidal compositions |
| NL292791A (id) * | 1962-05-16 | 1900-01-01 | ||
| DE1193044B (de) * | 1963-08-05 | 1965-05-20 | Bayer Ag | Verfahren zur Herstellung phosphorylierter Urethane |
| DE2512375A1 (de) * | 1975-03-21 | 1976-09-30 | Bayer Ag | 1-hydroxy-2,2,2-trichloraethan- thionophosphonsaeuredialkylester, verfahren zu ihrer herstellung sowie ihre verwendung als insektizide |
| US4950658A (en) * | 1988-12-06 | 1990-08-21 | Board Of Trustees Of Southern Illinois Univ. | Method of medical treatment of Alzheimer's disease |
-
1996
- 1996-04-25 DE DE19616471A patent/DE19616471A1/de not_active Withdrawn
-
1997
- 1997-04-17 CZ CZ983434A patent/CZ343498A3/cs unknown
- 1997-04-17 HU HU9903366A patent/HUP9903366A3/hu unknown
- 1997-04-17 PL PL97333464A patent/PL333464A1/xx unknown
- 1997-04-17 SK SK1463-98A patent/SK146398A3/sk unknown
- 1997-04-17 JP JP09538197A patent/JP2000510455A/ja active Pending
- 1997-04-17 KR KR1019980708502A patent/KR20000010611A/ko not_active Application Discontinuation
- 1997-04-17 BR BR9709300A patent/BR9709300A/pt not_active Application Discontinuation
- 1997-04-17 TR TR1998/02137T patent/TR199802137T2/xx unknown
- 1997-04-17 WO PCT/US1997/006469 patent/WO1997039756A1/en not_active Application Discontinuation
- 1997-04-17 AU AU24623/97A patent/AU2462397A/en not_active Abandoned
- 1997-04-17 CA CA002252567A patent/CA2252567A1/en not_active Abandoned
- 1997-04-17 IL IL12669897A patent/IL126698A0/xx unknown
- 1997-04-17 EP EP97920431A patent/EP0896540A1/en not_active Withdrawn
- 1997-04-24 ZA ZA9703538A patent/ZA973538B/xx unknown
- 1997-04-24 ID IDP971362A patent/ID16678A/id unknown
- 1997-04-25 AR ARP970101724A patent/AR006870A1/es unknown
-
1998
- 1998-10-22 BG BG102864A patent/BG102864A/xx unknown
- 1998-10-23 NO NO984964A patent/NO984964L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| ID16678A (id) | 1997-10-30 |
| SK146398A3 (en) | 1999-06-11 |
| CZ343498A3 (cs) | 1999-02-17 |
| PL333464A1 (en) | 1999-12-20 |
| AR006870A1 (es) | 1999-09-29 |
| BG102864A (en) | 1999-09-30 |
| HUP9903366A3 (en) | 2000-08-28 |
| WO1997039756A1 (en) | 1997-10-30 |
| HUP9903366A2 (en) | 2000-07-28 |
| TR199802137T2 (xx) | 1999-02-22 |
| DE19616471A1 (de) | 1997-10-30 |
| NO984964D0 (no) | 1998-10-23 |
| BR9709300A (pt) | 1999-08-10 |
| EP0896540A1 (en) | 1999-02-17 |
| ZA973538B (en) | 1997-11-18 |
| CA2252567A1 (en) | 1997-10-30 |
| IL126698A0 (en) | 1999-08-17 |
| NO984964L (no) | 1998-12-22 |
| JP2000510455A (ja) | 2000-08-15 |
| KR20000010611A (ko) | 2000-02-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK5 | Application lapsed section 142(2)(e) - patent request and compl. specification not accepted |