NO128070B - - Google Patents
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- Publication number
- NO128070B NO128070B NO03010/70A NO301070A NO128070B NO 128070 B NO128070 B NO 128070B NO 03010/70 A NO03010/70 A NO 03010/70A NO 301070 A NO301070 A NO 301070A NO 128070 B NO128070 B NO 128070B
- Authority
- NO
- Norway
- Prior art keywords
- mol
- dihydro
- dibenzo
- methyl
- piperazinyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 41
- 229910052783 alkali metal Inorganic materials 0.000 claims description 23
- 150000001340 alkali metals Chemical class 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 16
- 239000007795 chemical reaction product Substances 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 14
- 150000002148 esters Chemical class 0.000 claims description 12
- 150000007522 mineralic acids Chemical class 0.000 claims description 7
- 150000007524 organic acids Chemical class 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 235000005985 organic acids Nutrition 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 150000008624 imidazolidinones Chemical class 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims 1
- 108090000623 proteins and genes Proteins 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 120
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 111
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 77
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
- 239000000243 solution Substances 0.000 description 41
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 33
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 29
- 239000000155 melt Substances 0.000 description 29
- 235000019441 ethanol Nutrition 0.000 description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 24
- -1 methanesulfonic acid ester Chemical class 0.000 description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 23
- 239000011541 reaction mixture Substances 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 18
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
- 239000002904 solvent Substances 0.000 description 14
- 238000010992 reflux Methods 0.000 description 13
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 12
- 235000019341 magnesium sulphate Nutrition 0.000 description 12
- 239000002253 acid Substances 0.000 description 11
- 239000002585 base Substances 0.000 description 11
- 239000012458 free base Substances 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 9
- 239000007858 starting material Substances 0.000 description 9
- 239000005457 ice water Substances 0.000 description 8
- 239000012074 organic phase Substances 0.000 description 8
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 8
- 239000003208 petroleum Substances 0.000 description 8
- 229910000027 potassium carbonate Inorganic materials 0.000 description 8
- 239000008346 aqueous phase Substances 0.000 description 7
- AFVFQIVMOAPDHO-UHFFFAOYSA-N methanesulfonic acid Substances CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- UHFHPJZMDZGQEU-UHFFFAOYSA-N 9-chloro-6-methoxytricyclo[9.4.0.03,8]pentadeca-1(15),3(8),4,6,11,13-hexaene Chemical compound COC=1C=CC2=C(C(CC3=C(C2)C=CC=C3)Cl)C1 UHFHPJZMDZGQEU-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000012043 crude product Substances 0.000 description 6
- LNOQURRKNJKKBU-UHFFFAOYSA-N ethyl piperazine-1-carboxylate Chemical compound CCOC(=O)N1CCNCC1 LNOQURRKNJKKBU-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 235000011121 sodium hydroxide Nutrition 0.000 description 6
- MXVLBMCJFVQLHH-UHFFFAOYSA-N 1-methyl-3-(2-piperazin-1-ylethyl)imidazolidin-2-one Chemical compound O=C1N(C)CCN1CCN1CCNCC1 MXVLBMCJFVQLHH-UHFFFAOYSA-N 0.000 description 5
- RMUJDFSDKNQTSW-UHFFFAOYSA-N CC=1C=CC2=C(C(CC3=C(C2)C=CC=C3)Cl)C1 Chemical compound CC=1C=CC2=C(C(CC3=C(C2)C=CC=C3)Cl)C1 RMUJDFSDKNQTSW-UHFFFAOYSA-N 0.000 description 5
- DRKKMVMHHKMUTC-UHFFFAOYSA-N CC=1C=CC2=C(C(CC3=C(C2)C=CC=C3)N3CCNCC3)C1 Chemical compound CC=1C=CC2=C(C(CC3=C(C2)C=CC=C3)N3CCNCC3)C1 DRKKMVMHHKMUTC-UHFFFAOYSA-N 0.000 description 5
- 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 5
- 239000000706 filtrate Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- KYUINFOTNHJUSI-UHFFFAOYSA-N 1,1-bis(2-chloroethyl)-3-methylurea Chemical compound CNC(=O)N(CCCl)CCCl KYUINFOTNHJUSI-UHFFFAOYSA-N 0.000 description 4
- NUTYGYJJFANDDP-UHFFFAOYSA-N 1,1-bis(2-chloroethyl)-3-propan-2-ylurea Chemical compound CC(C)NC(=O)N(CCCl)CCCl NUTYGYJJFANDDP-UHFFFAOYSA-N 0.000 description 4
- PGLGGIMEUXCCDC-UHFFFAOYSA-N 1-(2-chloroethyl)-3-methylimidazolidin-2-one Chemical compound CN1CCN(CCCl)C1=O PGLGGIMEUXCCDC-UHFFFAOYSA-N 0.000 description 4
- FGEQPHQXHJNFLV-UHFFFAOYSA-N 1-(2-chloroethyl)-3-propan-2-ylimidazolidin-2-one Chemical compound CC(C)N1CCN(CCCl)C1=O FGEQPHQXHJNFLV-UHFFFAOYSA-N 0.000 description 4
- ZYDRQRGJQXQGBW-UHFFFAOYSA-N 1-methyl-3-[2-[4-(3-methyl-6,11-dihydro-5h-dibenzo[2,1-b:1',2'-f][7]annulen-5-yl)piperazin-1-yl]ethyl]imidazolidin-2-one Chemical compound O=C1N(C)CCN1CCN1CCN(C2C3=CC(C)=CC=C3CC3=CC=CC=C3C2)CC1 ZYDRQRGJQXQGBW-UHFFFAOYSA-N 0.000 description 4
- QKKGXXPAYQUYPJ-UHFFFAOYSA-N 9-chloro-2-methyltricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,11,13-hexaene Chemical compound CC1C2=C(C(CC3=C1C=CC=C3)Cl)C=CC=C2 QKKGXXPAYQUYPJ-UHFFFAOYSA-N 0.000 description 4
- ZUFATOHAGXKQCP-UHFFFAOYSA-N CC1C2=C(C(CC3=C1C=CC=C3)N3CCNCC3)C=CC=C2 Chemical compound CC1C2=C(C(CC3=C1C=CC=C3)N3CCNCC3)C=CC=C2 ZUFATOHAGXKQCP-UHFFFAOYSA-N 0.000 description 4
- HTMJUXPDXSKVGE-UHFFFAOYSA-N ClC=1C=CC2=C(C(CC3=C(C2)C=CC=C3)N3CCNCC3)C1 Chemical compound ClC=1C=CC2=C(C(CC3=C(C2)C=CC=C3)N3CCNCC3)C1 HTMJUXPDXSKVGE-UHFFFAOYSA-N 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 239000011230 binding agent Substances 0.000 description 4
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 4
- 229940098779 methanesulfonic acid Drugs 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- BKWPKBBPNYTXEP-UHFFFAOYSA-N 1-(3-chloropropyl)-3-ethylimidazolidin-2-one Chemical compound CCN1CCN(CCCCl)C1=O BKWPKBBPNYTXEP-UHFFFAOYSA-N 0.000 description 3
- QBHAQYJNTMNFSK-UHFFFAOYSA-N 1-(3-chloropropyl)-3-methylimidazolidin-2-one Chemical compound CN1CCN(CCCCl)C1=O QBHAQYJNTMNFSK-UHFFFAOYSA-N 0.000 description 3
- LBQMWHNSJSECCD-UHFFFAOYSA-N 1-(9-tricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,11,13-hexaenyl)piperazine Chemical compound N1(CCNCC1)C1CC2=C(CC3=C1C=CC=C3)C=CC=C2 LBQMWHNSJSECCD-UHFFFAOYSA-N 0.000 description 3
- BVHDXFBAHDJHEY-UHFFFAOYSA-N 1-butyl-3-(3-chloropropyl)imidazolidin-2-one Chemical compound ClCCCN1C(N(CC1)CCCC)=O BVHDXFBAHDJHEY-UHFFFAOYSA-N 0.000 description 3
- MBXUQLQMXRTGJL-UHFFFAOYSA-N 9-chloro-2,6-dimethyltricyclo[9.4.0.03,8]pentadeca-1(15),3(8),4,6,11,13-hexaene Chemical compound CC1C2=C(C(CC3=C1C=CC=C3)Cl)C=C(C=C2)C MBXUQLQMXRTGJL-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OAVZVFDZDIOERN-UHFFFAOYSA-N CC1C2=C(C(CC3=C1C=CC=C3)N3CCNCC3)C=C(C=C2)C Chemical compound CC1C2=C(C(CC3=C1C=CC=C3)N3CCNCC3)C=C(C=C2)C OAVZVFDZDIOERN-UHFFFAOYSA-N 0.000 description 3
- IVMKCMCCRBERCA-UHFFFAOYSA-N COC=1C=CC2=C(C(CC3=C(C2)C=CC=C3)N3CCNCC3)C1 Chemical compound COC=1C=CC2=C(C(CC3=C(C2)C=CC=C3)N3CCNCC3)C1 IVMKCMCCRBERCA-UHFFFAOYSA-N 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 238000011065 in-situ storage Methods 0.000 description 3
- 150000002641 lithium Chemical class 0.000 description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
- 239000011976 maleic acid Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 235000006408 oxalic acid Nutrition 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- 150000003672 ureas Chemical class 0.000 description 3
- HPNMBPJZEUUHQY-UHFFFAOYSA-N 1-(2-piperazin-1-ylethyl)-3-propan-2-ylimidazolidin-2-one Chemical compound O=C1N(C(C)C)CCN1CCN1CCNCC1 HPNMBPJZEUUHQY-UHFFFAOYSA-N 0.000 description 2
- DRNIBHYQCXSSHD-UHFFFAOYSA-N 1-butyl-3-(3-piperazin-1-ylpropyl)imidazolidin-2-one Chemical compound N1(CCNCC1)CCCN1C(N(CC1)CCCC)=O DRNIBHYQCXSSHD-UHFFFAOYSA-N 0.000 description 2
- RQAVSDINDRNIKL-UHFFFAOYSA-N 1-chloro-3-isocyanatopropane Chemical compound ClCCCN=C=O RQAVSDINDRNIKL-UHFFFAOYSA-N 0.000 description 2
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 2
- GSLTVFIVJMCNBH-UHFFFAOYSA-N 2-isocyanatopropane Chemical compound CC(C)N=C=O GSLTVFIVJMCNBH-UHFFFAOYSA-N 0.000 description 2
- TVMMCNUFPLVPAS-UHFFFAOYSA-N 2-methyltricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,11,13-hexaen-9-ol Chemical compound CC1C2=C(C(CC3=C1C=CC=C3)O)C=CC=C2 TVMMCNUFPLVPAS-UHFFFAOYSA-N 0.000 description 2
- YRMDZVGRJNWWTR-UHFFFAOYSA-N 3-butyl-1,1-bis(2-chloroethyl)urea Chemical compound CCCCNC(=O)N(CCCl)CCCl YRMDZVGRJNWWTR-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-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
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 2
- 150000008046 alkali metal hydrides Chemical class 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 150000001649 bromium compounds Chemical class 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- ZXIJMRYMVAMXQP-UHFFFAOYSA-N cycloheptene Chemical compound C1CCC=CCC1 ZXIJMRYMVAMXQP-UHFFFAOYSA-N 0.000 description 2
- NPOMSUOUAZCMBL-UHFFFAOYSA-N dichloromethane;ethoxyethane Chemical compound ClCCl.CCOCC NPOMSUOUAZCMBL-UHFFFAOYSA-N 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- FKWPWZBCUPMCRQ-UHFFFAOYSA-N ethyl 4-[3-(3-butyl-2-oxoimidazolidin-1-yl)propyl]piperazine-1-carboxylate Chemical compound C(C)OC(=O)N1CCN(CC1)CCCN1C(N(CC1)CCCC)=O FKWPWZBCUPMCRQ-UHFFFAOYSA-N 0.000 description 2
- 230000007717 exclusion Effects 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N p-toluenesulfonic acid Substances CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- VEEUFWDGCHUMFT-UHFFFAOYSA-N 1,1-bis(2-hydroxyethyl)-3-methylurea Chemical compound CNC(=O)N(CCO)CCO VEEUFWDGCHUMFT-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- VZURDTLKOLXHIG-UHFFFAOYSA-N 1-[2-[4-(6-chloro-9-tricyclo[9.4.0.03,8]pentadeca-1(15),3(8),4,6,11,13-hexaenyl)piperazin-1-yl]ethyl]-3-methylimidazolidin-2-one Chemical compound ClC=1C=CC2=C(C(CC3=C(C2)C=CC=C3)N3CCN(CC3)CCN3C(N(CC3)C)=O)C1 VZURDTLKOLXHIG-UHFFFAOYSA-N 0.000 description 1
- IJOYWYPOUHSRNJ-UHFFFAOYSA-N 1-[2-[4-(6-methoxy-9-tricyclo[9.4.0.03,8]pentadeca-1(15),3(8),4,6,11,13-hexaenyl)piperazin-1-yl]ethyl]-3-methylimidazolidin-2-one Chemical compound COC=1C=CC2=C(C(CC3=C(C2)C=CC=C3)N3CCN(CC3)CCN3C(N(CC3)C)=O)C1 IJOYWYPOUHSRNJ-UHFFFAOYSA-N 0.000 description 1
- WXFCSRRDIDFPCN-UHFFFAOYSA-N 1-[3-[4-(2,6-dimethyl-9-tricyclo[9.4.0.03,8]pentadeca-1(15),3(8),4,6,11,13-hexaenyl)piperazin-1-yl]propyl]-3-methylimidazolidin-2-one Chemical compound CC1C2=C(C(CC3=C1C=CC=C3)N3CCN(CC3)CCCN3C(N(CC3)C)=O)C=C(C=C2)C WXFCSRRDIDFPCN-UHFFFAOYSA-N 0.000 description 1
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 1
- ILBUTIXHGQRMBR-UHFFFAOYSA-N 1-butyl-1-(2-chloroethyl)-3-(3-chloropropyl)urea Chemical compound C(CCC)N(C(=O)NCCCCl)CCCl ILBUTIXHGQRMBR-UHFFFAOYSA-N 0.000 description 1
- BOJIHTRFJASSFW-UHFFFAOYSA-N 1-butyl-3-(2-chloroethyl)imidazolidin-2-one Chemical compound CCCCN1CCN(CCCl)C1=O BOJIHTRFJASSFW-UHFFFAOYSA-N 0.000 description 1
- QAIDOLIDQPBPNK-UHFFFAOYSA-N 1-ethyl-3-(3-piperazin-1-ylpropyl)imidazolidin-2-one Chemical compound O=C1N(CC)CCN1CCCN1CCNCC1 QAIDOLIDQPBPNK-UHFFFAOYSA-N 0.000 description 1
- DFWFWPZOZJUZOK-UHFFFAOYSA-N 1-methyl-3-(3-piperazin-1-ylpropyl)imidazolidin-2-one Chemical compound N1(CCNCC1)CCCN1C(N(CC1)C)=O DFWFWPZOZJUZOK-UHFFFAOYSA-N 0.000 description 1
- HJJAJUFETDAZNY-UHFFFAOYSA-N 2,6-dimethyltricyclo[9.4.0.03,8]pentadeca-1(15),3(8),4,6,11,13-hexaen-9-one Chemical compound CC1C2=C(C(CC3=C1C=CC=C3)=O)C=C(C=C2)C HJJAJUFETDAZNY-UHFFFAOYSA-N 0.000 description 1
- LJDSTRZHPWMDPG-UHFFFAOYSA-N 2-(butylamino)ethanol Chemical compound CCCCNCCO LJDSTRZHPWMDPG-UHFFFAOYSA-N 0.000 description 1
- MIJDSYMOBYNHOT-UHFFFAOYSA-N 2-(ethylamino)ethanol Chemical compound CCNCCO MIJDSYMOBYNHOT-UHFFFAOYSA-N 0.000 description 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
- WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical compound O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- RJWBTWIBUIGANW-UHFFFAOYSA-N 4-chlorobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(Cl)C=C1 RJWBTWIBUIGANW-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- BEJNWIREUXTIMO-UHFFFAOYSA-N 9-chlorotricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,11,13-hexaene Chemical compound ClC1CC2=C(CC3=C1C=CC=C3)C=CC=C2 BEJNWIREUXTIMO-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- WSPRZLMIITXPSN-UHFFFAOYSA-N C(C=C/C(=O)O)(=O)O.C(C=C/C(=O)O)(=O)O.CC=1C=CC2=C(C(CC3=C(C2)C=CC=C3)N3CCN(CC3)CCN3C(N(CC3)C)=O)C1 Chemical compound C(C=C/C(=O)O)(=O)O.C(C=C/C(=O)O)(=O)O.CC=1C=CC2=C(C(CC3=C(C2)C=CC=C3)N3CCN(CC3)CCN3C(N(CC3)C)=O)C1 WSPRZLMIITXPSN-UHFFFAOYSA-N 0.000 description 1
- ZIXRNXJCZDJFPD-UHFFFAOYSA-N CC1C2=C(C(CC3=C1C=CC=C3)N3CCN(CC3)CCN3C(N(CC3)C)=O)C=C(C=C2)C Chemical compound CC1C2=C(C(CC3=C1C=CC=C3)N3CCN(CC3)CCN3C(N(CC3)C)=O)C=C(C=C2)C ZIXRNXJCZDJFPD-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 208000010513 Stupor Diseases 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 239000000219 Sympatholytic Substances 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 229940008309 acetone / ethanol Drugs 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 230000003474 anti-emetic effect Effects 0.000 description 1
- 239000006286 aqueous extract Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000003874 central nervous system depressant Substances 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- LJQKCYFTNDAAPC-UHFFFAOYSA-N ethanol;ethyl acetate Chemical compound CCO.CCOC(C)=O LJQKCYFTNDAAPC-UHFFFAOYSA-N 0.000 description 1
- XTLNYNMNUCLWEZ-UHFFFAOYSA-N ethanol;propan-2-one Chemical compound CCO.CC(C)=O XTLNYNMNUCLWEZ-UHFFFAOYSA-N 0.000 description 1
- MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 1
- QVDYYQXUNAQSNI-UHFFFAOYSA-N ethyl acetate;pentane Chemical compound CCCCC.CCOC(C)=O QVDYYQXUNAQSNI-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 1
- 235000019799 monosodium phosphate Nutrition 0.000 description 1
- 230000004899 motility Effects 0.000 description 1
- HNHVTXYLRVGMHD-UHFFFAOYSA-N n-butyl isocyanate Chemical compound CCCCN=C=O HNHVTXYLRVGMHD-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000007530 organic bases Chemical group 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical class OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000000948 sympatholitic effect Effects 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/30—Oxygen or sulfur atoms
- C07D233/32—One oxygen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1212069A CH513189A (de) | 1969-08-11 | 1969-08-11 | Verfahren zur Herstellung von neuen Imidazolidinonderivaten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO128070B true NO128070B (de) | 1973-09-24 |
Family
ID=4380047
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO03010/70A NO128070B (de) | 1969-08-11 | 1970-08-04 |
Country Status (15)
| Country | Link |
|---|---|
| US (2) | US3720676A (de) |
| AT (1) | AT294080B (de) |
| AU (1) | AU1859270A (de) |
| BE (1) | BE754642A (de) |
| CH (3) | CH513189A (de) |
| DE (1) | DE2039722C3 (de) |
| DK (1) | DK127117B (de) |
| ES (3) | ES382621A1 (de) |
| FR (1) | FR2068484B1 (de) |
| GB (1) | GB1325354A (de) |
| IE (1) | IE34450B1 (de) |
| IL (1) | IL35087A (de) |
| NL (1) | NL7011529A (de) |
| NO (1) | NO128070B (de) |
| ZA (1) | ZA705502B (de) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2278340A1 (fr) * | 1974-07-17 | 1976-02-13 | Delalande Sa | Nouveau derive de la n-(trimethoxy-3,4,5 cinnamoyl) piperazine, ses sels d'addition d'acides, son procede de preparation et son application en therapeutique |
| DE3009045A1 (de) * | 1980-03-08 | 1981-09-24 | Basf Ag, 6700 Ludwigshafen | 10-substituierte 5-cyanmethylen-10,11-dihydro-dibenzo-(a,d) -cycloheptene |
| DE3014157A1 (de) * | 1980-04-12 | 1981-10-22 | Hoechst Ag, 6000 Frankfurt | Fungizide, heterocyclisch substituierte thioglykolsaeureanilide |
| US4878236A (en) * | 1988-12-02 | 1989-10-31 | Ray Donald K | Automatic emergency locator system and method |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1243199B (de) * | 1964-02-28 | 1967-06-29 | Asta Werke Ag Chem Fab | Verfahren zur Herstellung neuer Phenthiazinderivate |
| DE1931193A1 (de) * | 1968-06-20 | 1970-01-02 | Geigy Ag J R | Verfahren zur Herstellung von neuen Imidazolidinonderivaten |
| FR1505347A (fr) * | 1965-12-28 | 1967-12-15 | Rhone Poulenc Sa | Nouveaux dérivés du dibenzocycloheptadiène et leur préparation |
| NL7004059A (de) * | 1969-03-28 | 1970-09-30 |
-
0
- BE BE754642D patent/BE754642A/xx unknown
-
1969
- 1969-08-11 CH CH1212069A patent/CH513189A/de not_active IP Right Cessation
- 1969-08-11 CH CH902871A patent/CH513190A/de not_active IP Right Cessation
- 1969-08-11 CH CH902971A patent/CH513191A/de not_active IP Right Cessation
-
1970
- 1970-08-04 NL NL7011529A patent/NL7011529A/xx unknown
- 1970-08-04 DK DK401070AA patent/DK127117B/da unknown
- 1970-08-04 NO NO03010/70A patent/NO128070B/no unknown
- 1970-08-05 US US00061435A patent/US3720676A/en not_active Expired - Lifetime
- 1970-08-07 FR FR707029219A patent/FR2068484B1/fr not_active Expired
- 1970-08-10 GB GB3840570A patent/GB1325354A/en not_active Expired
- 1970-08-10 IE IE1034/70A patent/IE34450B1/xx unknown
- 1970-08-10 DE DE2039722A patent/DE2039722C3/de not_active Expired
- 1970-08-10 ZA ZA705502A patent/ZA705502B/xx unknown
- 1970-08-10 AT AT728170A patent/AT294080B/de not_active IP Right Cessation
- 1970-08-10 ES ES382621A patent/ES382621A1/es not_active Expired
- 1970-08-10 IL IL35087A patent/IL35087A/en unknown
- 1970-08-10 AU AU18592/70A patent/AU1859270A/en not_active Expired
- 1970-08-10 ES ES382619A patent/ES382619A1/es not_active Expired
- 1970-08-10 ES ES382618A patent/ES382618A1/es not_active Expired
-
1972
- 1972-12-21 US US00317341A patent/US3798325A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DE2039722A1 (de) | 1971-02-25 |
| AU1859270A (en) | 1972-02-17 |
| ES382618A1 (es) | 1972-11-16 |
| CH513190A (de) | 1971-09-30 |
| IL35087A0 (en) | 1970-10-30 |
| IE34450L (en) | 1971-02-11 |
| IE34450B1 (en) | 1975-05-14 |
| DE2039722C3 (de) | 1974-03-07 |
| AT294080B (de) | 1971-11-10 |
| ES382619A1 (es) | 1972-11-16 |
| US3720676A (en) | 1973-03-13 |
| CH513189A (de) | 1971-09-30 |
| BE754642A (fr) | 1971-02-10 |
| US3798325A (en) | 1974-03-19 |
| FR2068484B1 (de) | 1974-02-22 |
| CH513191A (de) | 1971-09-30 |
| NL7011529A (de) | 1971-02-15 |
| FR2068484A1 (de) | 1971-08-27 |
| ES382621A1 (es) | 1972-11-16 |
| DK127117B (da) | 1973-09-24 |
| GB1325354A (en) | 1973-08-01 |
| IL35087A (en) | 1973-01-30 |
| DE2039722B2 (de) | 1973-08-02 |
| ZA705502B (en) | 1971-04-28 |
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