BE564598A - - Google Patents
Info
- Publication number
- BE564598A BE564598A BE564598DA BE564598A BE 564598 A BE564598 A BE 564598A BE 564598D A BE564598D A BE 564598DA BE 564598 A BE564598 A BE 564598A
- Authority
- BE
- Belgium
- Prior art keywords
- anthraquinone
- salts
- solution
- water
- mixture
- Prior art date
Links
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 54
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 52
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 48
- 239000000203 mixture Substances 0.000 claims description 40
- -1 aminoalkyl halide Chemical group 0.000 claims description 31
- 238000010992 reflux Methods 0.000 claims description 31
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 29
- CTQNGGLPUBDAKN-UHFFFAOYSA-N o-xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 24
- 239000008096 xylene Substances 0.000 claims description 24
- 150000003839 salts Chemical class 0.000 claims description 22
- 239000011780 sodium chloride Substances 0.000 claims description 22
- 238000002844 melting Methods 0.000 claims description 21
- 238000001816 cooling Methods 0.000 claims description 20
- 238000007792 addition Methods 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 15
- 238000001914 filtration Methods 0.000 claims description 13
- 239000000706 filtrate Substances 0.000 claims description 12
- 238000001953 recrystallisation Methods 0.000 claims description 10
- 239000000725 suspension Substances 0.000 claims description 8
- CPELXLSAUQHCOX-UHFFFAOYSA-N hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 7
- KKZJGLLVHKMTCM-UHFFFAOYSA-N Mitoxantrone Chemical compound O=C1C2=C(O)C=CC(O)=C2C(=O)C2=C1C(NCCNCCO)=CC=C2NCCNCCO KKZJGLLVHKMTCM-UHFFFAOYSA-N 0.000 claims description 6
- 229960001156 Mitoxantrone Drugs 0.000 claims description 6
- 159000000001 potassium salts Chemical class 0.000 claims description 5
- GUEIZVNYDFNHJU-UHFFFAOYSA-N 1,4-Dihydroxyanthraquinone Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=CC=C2O GUEIZVNYDFNHJU-UHFFFAOYSA-N 0.000 claims description 4
- QBPFLULOKWLNNW-UHFFFAOYSA-N Dantron Chemical compound O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O QBPFLULOKWLNNW-UHFFFAOYSA-N 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 229960001577 dantron Drugs 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 150000004820 halides Chemical class 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- VSLYRNHVUOTNBV-UHFFFAOYSA-N 1,8-bis[2-(diethylamino)ethoxy]anthracene-9,10-dione Chemical compound O=C1C2=CC=CC(OCCN(CC)CC)=C2C(=O)C2=C1C=CC=C2OCCN(CC)CC VSLYRNHVUOTNBV-UHFFFAOYSA-N 0.000 claims description 2
- VTJBLEXKAAZZSL-UHFFFAOYSA-N 2-[2-(diethylamino)ethoxy]-1-hydroxyanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=C(O)C(OCCN(CC)CC)=CC=C3C(=O)C2=C1 VTJBLEXKAAZZSL-UHFFFAOYSA-N 0.000 claims description 2
- 150000002170 ethers Chemical class 0.000 claims description 2
- 150000004338 hydroxy anthraquinones Chemical class 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 125000002431 aminoalkoxy group Chemical group 0.000 claims 3
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N n-butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 2
- 229940036592 ANTHELMINTICS Drugs 0.000 claims 1
- 230000000507 anthelmentic Effects 0.000 claims 1
- 239000000921 anthelmintic agent Substances 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 82
- 239000000243 solution Substances 0.000 description 57
- 239000002585 base Substances 0.000 description 31
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 28
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 23
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 20
- 239000000155 melt Substances 0.000 description 19
- BTLXPCBPYBNQNR-UHFFFAOYSA-N 1-hydroxyanthraquinone Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2O BTLXPCBPYBNQNR-UHFFFAOYSA-N 0.000 description 17
- 230000001476 alcoholic Effects 0.000 description 17
- INQOMBQAUSQDDS-UHFFFAOYSA-N Methyl iodide Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 13
- 239000012458 free base Substances 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000001184 potassium carbonate Substances 0.000 description 10
- 229910000027 potassium carbonate Inorganic materials 0.000 description 10
- 238000002425 crystallisation Methods 0.000 description 9
- 230000005712 crystallization Effects 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N iso-propanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 159000000000 sodium salts Chemical class 0.000 description 6
- UFKAGGWFBTZZGY-UHFFFAOYSA-N 1-[2-(diethylamino)ethoxy]anthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2OCCN(CC)CC UFKAGGWFBTZZGY-UHFFFAOYSA-N 0.000 description 5
- YMDNODNLFSHHCV-UHFFFAOYSA-N 2-chloro-N,N-diethylethanamine Chemical compound CCN(CC)CCCl YMDNODNLFSHHCV-UHFFFAOYSA-N 0.000 description 5
- 239000007859 condensation product Substances 0.000 description 5
- 238000000605 extraction Methods 0.000 description 5
- GZUXJHMPEANEGY-UHFFFAOYSA-N Bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 4
- 230000002378 acidificating Effects 0.000 description 4
- NYYRRBOMNHUCLB-UHFFFAOYSA-N 3-chloro-N,N-dimethylpropan-1-amine Chemical compound CN(C)CCCCl NYYRRBOMNHUCLB-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- OCWGRWAYARCRTQ-UHFFFAOYSA-N 2-chloro-N,N-dimethylpropan-1-amine;hydron;chloride Chemical compound Cl.CC(Cl)CN(C)C OCWGRWAYARCRTQ-UHFFFAOYSA-N 0.000 description 2
- 125000000872 2-diethylaminoethoxy group Chemical group [H]C([H])([H])C([H])([H])N(C([H])([H])C([H])([H])[H])C([H])([H])C([H])([H])O* 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- 150000001350 alkyl halides Chemical class 0.000 description 2
- 230000005591 charge neutralization Effects 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 150000003840 hydrochlorides Chemical class 0.000 description 2
- 229940102396 methyl bromide Drugs 0.000 description 2
- 125000002757 morpholinyl group Chemical group 0.000 description 2
- 230000001264 neutralization Effects 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- UHIWBQIWXWWDKT-MRVPVSSYSA-N (4S)-4-hydroxy-2-(3-methoxypropyl)-1,1-dioxo-3,4-dihydrothieno[3,2-e]thiazine-6-sulfonamide Chemical compound O=S1(=O)N(CCCOC)C[C@@H](O)C2=C1SC(S(N)(=O)=O)=C2 UHIWBQIWXWWDKT-MRVPVSSYSA-N 0.000 description 1
- ASZLNPRMVCGYCI-UHFFFAOYSA-N 1$l^{2}-azolidine Chemical group C1CC[N]C1 ASZLNPRMVCGYCI-UHFFFAOYSA-N 0.000 description 1
- RNLWVACJCQQVGL-UHFFFAOYSA-N 1,2-bis[2-(diethylamino)ethoxy]anthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=C(OCCN(CC)CC)C(OCCN(CC)CC)=CC=C3C(=O)C2=C1 RNLWVACJCQQVGL-UHFFFAOYSA-N 0.000 description 1
- WNOAZUFOZKQFQU-UHFFFAOYSA-N 1,4-bis[2-(diethylamino)ethoxy]anthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(OCCN(CC)CC)=CC=C2OCCN(CC)CC WNOAZUFOZKQFQU-UHFFFAOYSA-N 0.000 description 1
- GGYJBLLDZHXFMM-UHFFFAOYSA-N 1,4-bis[3-(dimethylamino)propoxy]anthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(OCCCN(C)C)=CC=C2OCCCN(C)C GGYJBLLDZHXFMM-UHFFFAOYSA-N 0.000 description 1
- WYALCKNWMZWZCV-UHFFFAOYSA-N 1,8-bis[3-(dimethylamino)propoxy]anthracene-9,10-dione Chemical compound O=C1C2=CC=CC(OCCCN(C)C)=C2C(=O)C2=C1C=CC=C2OCCCN(C)C WYALCKNWMZWZCV-UHFFFAOYSA-N 0.000 description 1
- JEVSJZZZBAECIO-UHFFFAOYSA-N 1,8-bis[3-(dimethylamino)propoxy]anthracene-9,10-dione;hydrochloride Chemical compound Cl.O=C1C2=CC=CC(OCCCN(C)C)=C2C(=O)C2=C1C=CC=C2OCCCN(C)C JEVSJZZZBAECIO-UHFFFAOYSA-N 0.000 description 1
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-Bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 1
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-Chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 1
- ZIWAQSXOAVJZSG-UHFFFAOYSA-N 1-[3-(diethylamino)propoxy]anthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2OCCCN(CC)CC ZIWAQSXOAVJZSG-UHFFFAOYSA-N 0.000 description 1
- CGKODXHLTKSKLD-UHFFFAOYSA-N 1-[3-(dimethylamino)propoxy]anthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2OCCCN(C)C CGKODXHLTKSKLD-UHFFFAOYSA-N 0.000 description 1
- AVMHMVJVHYGDOO-UHFFFAOYSA-N 1-bromobut-2-ene Chemical compound CC=CCBr AVMHMVJVHYGDOO-UHFFFAOYSA-N 0.000 description 1
- ZMLUHYJUTIZTOJ-UHFFFAOYSA-N 1-chloro-N,N-dimethylpropan-2-amine Chemical compound ClCC(C)N(C)C ZMLUHYJUTIZTOJ-UHFFFAOYSA-N 0.000 description 1
- MNNZINNZIQVULG-UHFFFAOYSA-N 2-chloroethylbenzene Chemical compound ClCCC1=CC=CC=C1 MNNZINNZIQVULG-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
- WVUULNDRFBHTFG-UHFFFAOYSA-N 3-chloro-N,N-diethylpropan-1-amine Chemical compound CCN(CC)CCCCl WVUULNDRFBHTFG-UHFFFAOYSA-N 0.000 description 1
- FBDKONZGCAAZJK-UHFFFAOYSA-N 3-chloro-N,N-diethylpropan-1-amine;hydron;chloride Chemical compound Cl.CCN(CC)CCCCl FBDKONZGCAAZJK-UHFFFAOYSA-N 0.000 description 1
- RGCKGOZRHPZPFP-UHFFFAOYSA-N Alizarin Chemical compound C1=CC=C2C(=O)C3=C(O)C(O)=CC=C3C(=O)C2=C1 RGCKGOZRHPZPFP-UHFFFAOYSA-N 0.000 description 1
- BHELZAPQIKSEDF-UHFFFAOYSA-N Allyl bromide Chemical group BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
- 229940072107 Ascorbate Drugs 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N Benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N Benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- DWQYMRPOUGQEKU-UHFFFAOYSA-N C(C)N(CCCOC1=C(C=2C(C3=CC=CC=C3C(C=2C=C1)=O)=O)OCCCN(CC)CC)CC Chemical compound C(C)N(CCCOC1=C(C=2C(C3=CC=CC=C3C(C=2C=C1)=O)=O)OCCCN(CC)CC)CC DWQYMRPOUGQEKU-UHFFFAOYSA-N 0.000 description 1
- NEHMKBQYUWJMIP-UHFFFAOYSA-N Chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 1
- SOISCJIDWQCXLG-UHFFFAOYSA-N Cl.Cl.C(C)N(CCOC1=C(C=CC=2C(C3=CC=CC=C3C(C12)=O)=O)OCCN(CC)CC)CC Chemical compound Cl.Cl.C(C)N(CCOC1=C(C=CC=2C(C3=CC=CC=C3C(C12)=O)=O)OCCN(CC)CC)CC SOISCJIDWQCXLG-UHFFFAOYSA-N 0.000 description 1
- VLBHTAVZRZYEHR-UHFFFAOYSA-N Cl.Cl.O=C1C2=CC=CC=C2C(=O)C2=C1C(OCCN(CC)CC)=CC=C2OCCN(CC)CC Chemical compound Cl.Cl.O=C1C2=CC=CC=C2C(=O)C2=C1C(OCCN(CC)CC)=CC=C2OCCN(CC)CC VLBHTAVZRZYEHR-UHFFFAOYSA-N 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N Dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N Ethyl iodide Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- TYQCGQRIZGCHNB-JLAZNSOCSA-N L-ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(O)=C(O)C1=O TYQCGQRIZGCHNB-JLAZNSOCSA-N 0.000 description 1
- 229940050176 Methyl Chloride Drugs 0.000 description 1
- SNMVRZFUUCLYTO-UHFFFAOYSA-N N-Propyl chloride Chemical compound CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 description 1
- 241000975704 Syphacia Species 0.000 description 1
- 241000224526 Trichomonas Species 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K [O-]P([O-])([O-])=O Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- YVBSAPDHRXHFHV-UHFFFAOYSA-N [chloro(methoxy)methyl]benzene Chemical compound COC(Cl)C1=CC=CC=C1 YVBSAPDHRXHFHV-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- JPICKYUTICNNNJ-UHFFFAOYSA-N anthrarufin Chemical compound O=C1C2=C(O)C=CC=C2C(=O)C2=C1C=CC=C2O JPICKYUTICNNNJ-UHFFFAOYSA-N 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 229940038926 butyl chloride Drugs 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 150000004341 dihydroxyanthraquinones Chemical class 0.000 description 1
- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000001145 hydrido group Chemical group *[H] 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxyl anion Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 150000002829 nitrogen Chemical group 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-L oxalate Chemical compound [O-]C(=O)C([O-])=O MUBZPKHOEPUJKR-UHFFFAOYSA-L 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 125000005936 piperidyl group Chemical group 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 150000003613 toluenes Chemical class 0.000 description 1
- 230000001131 transforming Effects 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE564598A true BE564598A (cs) |
Family
ID=185409
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE564598D BE564598A (cs) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE564598A (cs) |
-
0
- BE BE564598D patent/BE564598A/fr unknown
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