DE1443216C3 - Verfahren zur Herstellung von Phenoxyalkylguanidinen und solche Verbindungen enthaltende Arzneimittel - Google Patents
Verfahren zur Herstellung von Phenoxyalkylguanidinen und solche Verbindungen enthaltende ArzneimittelInfo
- Publication number
- DE1443216C3 DE1443216C3 DE1443216A DE1443216A DE1443216C3 DE 1443216 C3 DE1443216 C3 DE 1443216C3 DE 1443216 A DE1443216 A DE 1443216A DE 1443216 A DE1443216 A DE 1443216A DE 1443216 C3 DE1443216 C3 DE 1443216C3
- Authority
- DE
- Germany
- Prior art keywords
- mixture
- water
- methylphenoxy
- ethanol
- general formula
- 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.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 title claims description 30
- 238000000034 method Methods 0.000 title claims description 11
- 238000002360 preparation method Methods 0.000 title claims description 4
- 239000003814 drug Substances 0.000 title claims description 3
- 150000003839 salts Chemical class 0.000 claims description 29
- 239000002253 acid Substances 0.000 claims description 18
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 10
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 10
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 5
- 229910021529 ammonia Inorganic materials 0.000 claims description 5
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 150000003863 ammonium salts Chemical class 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical group 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- 229910052801 chlorine Inorganic materials 0.000 claims 4
- 239000000460 chlorine Substances 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 239000004480 active ingredient Substances 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 146
- 239000000203 mixture Substances 0.000 description 88
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 71
- 235000019441 ethanol Nutrition 0.000 description 52
- 239000000243 solution Substances 0.000 description 47
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 45
- 238000002844 melting Methods 0.000 description 38
- 230000008018 melting Effects 0.000 description 38
- 238000009835 boiling Methods 0.000 description 36
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 34
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 33
- -1 lactic Chemical class 0.000 description 26
- BZZXQZOBAUXLHZ-UHFFFAOYSA-N (c-methylsulfanylcarbonimidoyl)azanium;sulfate Chemical compound CSC(N)=N.CSC(N)=N.OS(O)(=O)=O BZZXQZOBAUXLHZ-UHFFFAOYSA-N 0.000 description 22
- 150000001412 amines Chemical class 0.000 description 17
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical class C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 238000001953 recrystallisation Methods 0.000 description 15
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- 238000010438 heat treatment Methods 0.000 description 12
- 230000000948 sympatholitic effect Effects 0.000 description 12
- 230000000694 effects Effects 0.000 description 11
- FYRHIOVKTDQVFC-UHFFFAOYSA-M potassium phthalimide Chemical compound [K+].C1=CC=C2C(=O)[N-]C(=O)C2=C1 FYRHIOVKTDQVFC-UHFFFAOYSA-M 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 11
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 230000000507 anthelmentic effect Effects 0.000 description 9
- 241001480236 Strongyloides ratti Species 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- 210000000826 nictitating membrane Anatomy 0.000 description 7
- 229910000027 potassium carbonate Inorganic materials 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 6
- 239000000284 extract Substances 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 5
- 241000282326 Felis catus Species 0.000 description 5
- 125000001309 chloro group Chemical group Cl* 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 4
- UGRMITBWUVWUEB-UHFFFAOYSA-N 1-$l^{1}-oxidanyl-3-methylbenzene Chemical group CC1=CC=CC([O])=C1 UGRMITBWUVWUEB-UHFFFAOYSA-N 0.000 description 4
- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 description 4
- CFKMVGJGLGKFKI-UHFFFAOYSA-N 4-chloro-m-cresol Chemical compound CC1=CC(O)=CC=C1Cl CFKMVGJGLGKFKI-UHFFFAOYSA-N 0.000 description 4
- JGLWGLKNDHZFAP-UHFFFAOYSA-N C3-thiacarbocyanine cation Chemical compound S1C2=CC=CC=C2[N+](CC)=C1C=CC=C1N(CC)C2=CC=CC=C2S1 JGLWGLKNDHZFAP-UHFFFAOYSA-N 0.000 description 4
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical class CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- ZZTURJAZCMUWEP-UHFFFAOYSA-N diaminomethylideneazanium;hydrogen sulfate Chemical compound NC(N)=N.OS(O)(=O)=O ZZTURJAZCMUWEP-UHFFFAOYSA-N 0.000 description 4
- 229950007663 dithiazanine Drugs 0.000 description 4
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 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
- 239000002244 precipitate Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- SODQFLRLAOALCF-UHFFFAOYSA-N 1lambda3-bromacyclohexa-1,3,5-triene Chemical compound Br1=CC=CC=C1 SODQFLRLAOALCF-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 206010061217 Infestation Diseases 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- 239000000219 Sympatholytic Substances 0.000 description 3
- ZXJXZNDDNMQXFV-UHFFFAOYSA-M crystal violet Chemical compound [Cl-].C1=CC(N(C)C)=CC=C1[C+](C=1C=CC(=CC=1)N(C)C)C1=CC=C(N(C)C)C=C1 ZXJXZNDDNMQXFV-UHFFFAOYSA-M 0.000 description 3
- 239000002178 crystalline material Substances 0.000 description 3
- 229960001235 gentian violet Drugs 0.000 description 3
- 239000001294 propane Substances 0.000 description 3
- 239000008107 starch Substances 0.000 description 3
- 235000019698 starch Nutrition 0.000 description 3
- ZFHWDLYDBITDJK-UHFFFAOYSA-M 2-(2,6-dimethylphenoxy)ethyl-trimethylazanium;bromide Chemical compound [Br-].CC1=CC=CC(C)=C1OCC[N+](C)(C)C ZFHWDLYDBITDJK-UHFFFAOYSA-M 0.000 description 2
- ASHGTJPOSUFTGB-UHFFFAOYSA-N 3-methoxyphenol Chemical compound COC1=CC=CC(O)=C1 ASHGTJPOSUFTGB-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- 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 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 241000283984 Rodentia Species 0.000 description 2
- 241000244174 Strongyloides Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- UCTWMZQNUQWSLP-UHFFFAOYSA-N adrenaline Chemical compound CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 229940124339 anthelmintic agent Drugs 0.000 description 2
- 239000000921 anthelmintic agent Substances 0.000 description 2
- KVWNWTZZBKCOPM-UHFFFAOYSA-M bretylium tosylate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1.CC[N+](C)(C)CC1=CC=CC=C1Br KVWNWTZZBKCOPM-UHFFFAOYSA-M 0.000 description 2
- 150000001649 bromium compounds Chemical class 0.000 description 2
- 239000002026 chloroform extract Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 230000002040 relaxant effect Effects 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- MGSRCZKZVOBKFT-UHFFFAOYSA-N thymol Chemical compound CC(C)C1=CC=C(C)C=C1O MGSRCZKZVOBKFT-UHFFFAOYSA-N 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 1
- ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 1
- VEFLKXRACNJHOV-UHFFFAOYSA-N 1,3-dibromopropane Chemical compound BrCCCBr VEFLKXRACNJHOV-UHFFFAOYSA-N 0.000 description 1
- OEYZGSRLAGSENP-UHFFFAOYSA-N 1-(2-bromoethoxy)-2,4-dichlorobenzene Chemical compound ClC1=CC=C(OCCBr)C(Cl)=C1 OEYZGSRLAGSENP-UHFFFAOYSA-N 0.000 description 1
- ZDEJJQHQIOWTPC-UHFFFAOYSA-N 1-(2-bromoethoxy)-2-chlorobenzene Chemical compound ClC1=CC=CC=C1OCCBr ZDEJJQHQIOWTPC-UHFFFAOYSA-N 0.000 description 1
- DAGDLSRRQJATCV-UHFFFAOYSA-N 1-(2-bromoethoxy)-2-propan-2-ylbenzene Chemical compound CC(C)C1=CC=CC=C1OCCBr DAGDLSRRQJATCV-UHFFFAOYSA-N 0.000 description 1
- BTUZRSNUNBPIEN-UHFFFAOYSA-N 1-(2-bromoethoxy)-3-methoxybenzene Chemical compound COC1=CC=CC(OCCBr)=C1 BTUZRSNUNBPIEN-UHFFFAOYSA-N 0.000 description 1
- JVEQWIQHHWNMQX-UHFFFAOYSA-N 1-bromo-2-ethoxybenzene Chemical compound CCOC1=CC=CC=C1Br JVEQWIQHHWNMQX-UHFFFAOYSA-N 0.000 description 1
- SRGBSEMMGLSUMI-UHFFFAOYSA-N 1-bromo-4-(2-bromoethoxy)benzene Chemical compound BrCCOC1=CC=C(Br)C=C1 SRGBSEMMGLSUMI-UHFFFAOYSA-N 0.000 description 1
- HOLHYSJJBXSLMV-UHFFFAOYSA-N 2,6-dichlorophenol Chemical compound OC1=C(Cl)C=CC=C1Cl HOLHYSJJBXSLMV-UHFFFAOYSA-N 0.000 description 1
- SUSCJRQKCYABMX-UHFFFAOYSA-N 2-(2,4,6-trichlorophenoxy)ethanamine Chemical compound NCCOC1=C(Cl)C=C(Cl)C=C1Cl SUSCJRQKCYABMX-UHFFFAOYSA-N 0.000 description 1
- FRMFPBHRPGLVTF-UHFFFAOYSA-N 2-(2,6-dichlorophenoxy)ethanamine Chemical compound NCCOC1=C(Cl)C=CC=C1Cl FRMFPBHRPGLVTF-UHFFFAOYSA-N 0.000 description 1
- GFLHGSIWKATBCA-UHFFFAOYSA-N 2-(2-bromoethoxy)-1,3,5-trichlorobenzene Chemical compound ClC1=CC(Cl)=C(OCCBr)C(Cl)=C1 GFLHGSIWKATBCA-UHFFFAOYSA-N 0.000 description 1
- RQGVZXGJKYJQSN-UHFFFAOYSA-N 2-(2-bromoethoxy)-1,3-dichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1OCCBr RQGVZXGJKYJQSN-UHFFFAOYSA-N 0.000 description 1
- MSKAVXYLXIUCJP-UHFFFAOYSA-N 2-(2-bromoethoxy)-1,3-dimethylbenzene Chemical compound CC1=CC=CC(C)=C1OCCBr MSKAVXYLXIUCJP-UHFFFAOYSA-N 0.000 description 1
- JBISLHJJABQJNR-UHFFFAOYSA-N 2-(2-bromoethoxy)-1,4-dimethylbenzene Chemical compound CC1=CC=C(C)C(OCCBr)=C1 JBISLHJJABQJNR-UHFFFAOYSA-N 0.000 description 1
- UWRFNXLTMNVOTG-UHFFFAOYSA-N 2-(2-bromophenoxy)ethanamine Chemical compound NCCOC1=CC=CC=C1Br UWRFNXLTMNVOTG-UHFFFAOYSA-N 0.000 description 1
- NAPNYPMMDVRKGM-UHFFFAOYSA-N 2-(2-chlorophenoxy)ethanamine Chemical compound NCCOC1=CC=CC=C1Cl NAPNYPMMDVRKGM-UHFFFAOYSA-N 0.000 description 1
- ZCMYPKSIEFFUBO-UHFFFAOYSA-N 2-(2-phenoxyethyl)guanidine Chemical class NC(=N)NCCOC1=CC=CC=C1 ZCMYPKSIEFFUBO-UHFFFAOYSA-N 0.000 description 1
- HGULZMCXEYYSSI-UHFFFAOYSA-N 2-(2-propan-2-ylphenoxy)ethanamine Chemical compound CC(C)C1=CC=CC=C1OCCN HGULZMCXEYYSSI-UHFFFAOYSA-N 0.000 description 1
- MYYLGENPKRDZMK-UHFFFAOYSA-N 2-(3-methylphenoxy)propan-1-amine Chemical compound NCC(C)OC1=CC=CC(C)=C1 MYYLGENPKRDZMK-UHFFFAOYSA-N 0.000 description 1
- NVECNFGARHPBLU-UHFFFAOYSA-N 2-(3-methylphenoxy)propanoic acid Chemical compound OC(=O)C(C)OC1=CC=CC(C)=C1 NVECNFGARHPBLU-UHFFFAOYSA-N 0.000 description 1
- ZZOAGCQCHPHGCF-UHFFFAOYSA-N 2-(3-methylphenoxy)propanoyl chloride Chemical compound ClC(=O)C(C)OC1=CC=CC(C)=C1 ZZOAGCQCHPHGCF-UHFFFAOYSA-N 0.000 description 1
- XRNJQYPOXIRDCV-UHFFFAOYSA-N 2-(4-chloro-2-methylphenoxy)ethanamine Chemical compound CC1=CC(Cl)=CC=C1OCCN XRNJQYPOXIRDCV-UHFFFAOYSA-N 0.000 description 1
- BDMIIOXQERVSLH-UHFFFAOYSA-N 2-(4-chloro-3-methylphenoxy)ethanamine Chemical compound CC1=CC(OCCN)=CC=C1Cl BDMIIOXQERVSLH-UHFFFAOYSA-N 0.000 description 1
- WRJHHZOBJGDIHT-UHFFFAOYSA-N 2-(4-methylphenoxy)ethanamine Chemical compound CC1=CC=C(OCCN)C=C1 WRJHHZOBJGDIHT-UHFFFAOYSA-N 0.000 description 1
- KRQUFUKTQHISJB-YYADALCUSA-N 2-[(E)-N-[2-(4-chlorophenoxy)propoxy]-C-propylcarbonimidoyl]-3-hydroxy-5-(thian-3-yl)cyclohex-2-en-1-one Chemical compound CCC\C(=N/OCC(C)OC1=CC=C(Cl)C=C1)C1=C(O)CC(CC1=O)C1CCCSC1 KRQUFUKTQHISJB-YYADALCUSA-N 0.000 description 1
- CKEYBAHJDLWWBQ-UHFFFAOYSA-N 2-[2-(2,6-dimethylphenoxy)ethyl]guanidine Chemical compound CC1=CC=CC(C)=C1OCCN=C(N)N CKEYBAHJDLWWBQ-UHFFFAOYSA-N 0.000 description 1
- OSQCAQYMDXTKSE-UHFFFAOYSA-N 2-[2-(2,6-dimethylphenoxy)ethyl]guanidine sulfuric acid Chemical compound S(=O)(=O)(O)O.CC1=C(OCCNC(=N)N)C(=CC=C1)C OSQCAQYMDXTKSE-UHFFFAOYSA-N 0.000 description 1
- IZTPIYVLPJHKSN-UHFFFAOYSA-N 2-[2-(2,6-dimethylphenoxy)propyl]guanidine Chemical compound NC(N)=NCC(C)OC1=C(C)C=CC=C1C IZTPIYVLPJHKSN-UHFFFAOYSA-N 0.000 description 1
- ZEOQXYUPHYZGPK-UHFFFAOYSA-N 2-[2-(2,6-dimethylphenoxy)propyl]guanidine sulfuric acid Chemical compound S(=O)(=O)(O)O.CC1=C(OC(CNC(=N)N)C)C(=CC=C1)C ZEOQXYUPHYZGPK-UHFFFAOYSA-N 0.000 description 1
- FJAVHCJNPRHQSZ-UHFFFAOYSA-N 2-[2-(2-bromophenoxy)ethyl]guanidine sulfuric acid Chemical compound S(=O)(=O)(O)O.BrC1=C(OCCNC(=N)N)C=CC=C1 FJAVHCJNPRHQSZ-UHFFFAOYSA-N 0.000 description 1
- UHKHAQCLGZOYKX-UHFFFAOYSA-N 2-[2-(2-chloro-6-methylphenoxy)ethyl]guanidine sulfuric acid Chemical compound S(=O)(=O)(O)O.ClC1=C(OCCNC(=N)N)C(=CC=C1)C UHKHAQCLGZOYKX-UHFFFAOYSA-N 0.000 description 1
- HUECQLXECHCLKX-UHFFFAOYSA-N 2-[2-(2-chlorophenoxy)ethyl]guanidine sulfuric acid Chemical compound S(=O)(=O)(O)O.ClC1=C(OCCNC(=N)N)C=CC=C1 HUECQLXECHCLKX-UHFFFAOYSA-N 0.000 description 1
- UEWWDYAZLCLFOP-UHFFFAOYSA-N 2-[2-(2-propan-2-ylphenoxy)ethyl]guanidine sulfuric acid Chemical compound S(=O)(=O)(O)O.C(C)(C)C1=C(OCCNC(=N)N)C=CC=C1 UEWWDYAZLCLFOP-UHFFFAOYSA-N 0.000 description 1
- ZDQNEDISHIEEJC-UHFFFAOYSA-N 2-[2-(3-methylphenoxy)ethyl]guanidine sulfuric acid Chemical compound S(=O)(=O)(O)O.CC=1C=C(OCCNC(=N)N)C=CC1 ZDQNEDISHIEEJC-UHFFFAOYSA-N 0.000 description 1
- VAFMUIWXPGGCAE-UHFFFAOYSA-N 2-[2-(4-chloro-5-methyl-2-propan-2-ylphenoxy)ethyl]guanidine Chemical compound ClC1=CC(=C(OCCNC(=N)N)C=C1C)C(C)C VAFMUIWXPGGCAE-UHFFFAOYSA-N 0.000 description 1
- ILUKRBCVXXYEAL-UHFFFAOYSA-N 2-[2-(4-chloro-5-methyl-2-propan-2-ylphenoxy)ethyl]guanidine sulfuric acid Chemical compound S(=O)(=O)(O)O.ClC1=CC(=C(OCCNC(=N)N)C=C1C)C(C)C ILUKRBCVXXYEAL-UHFFFAOYSA-N 0.000 description 1
- IQQDWKYHEKMNNW-UHFFFAOYSA-N 2-[2-(4-chlorophenoxy)ethyl]guanidine sulfuric acid Chemical compound S(=O)(=O)(O)O.ClC1=CC=C(OCCNC(=N)N)C=C1 IQQDWKYHEKMNNW-UHFFFAOYSA-N 0.000 description 1
- DDUKKYVMOSHFIS-UHFFFAOYSA-N 2-[2-(4-methylphenoxy)ethyl]guanidine sulfuric acid Chemical compound S(=O)(=O)(O)O.CC1=CC=C(OCCNC(=N)N)C=C1 DDUKKYVMOSHFIS-UHFFFAOYSA-N 0.000 description 1
- YPNZJHFXFVLXSE-UHFFFAOYSA-N 2-chloro-6-methylphenol Chemical compound CC1=CC=CC(Cl)=C1O YPNZJHFXFVLXSE-UHFFFAOYSA-N 0.000 description 1
- VQZRLBWPEHFGCD-UHFFFAOYSA-N 3-chloro-4-methylphenol Chemical compound CC1=CC=C(O)C=C1Cl VQZRLBWPEHFGCD-UHFFFAOYSA-N 0.000 description 1
- AQJFATAFTQCRGC-UHFFFAOYSA-N 3-chloro-4-methylphenol Natural products CC1=CC=C(O)C(Cl)=C1 AQJFATAFTQCRGC-UHFFFAOYSA-N 0.000 description 1
- OSDLLIBGSJNGJE-UHFFFAOYSA-N 4-chloro-3,5-dimethylphenol Chemical compound CC1=CC(O)=CC(C)=C1Cl OSDLLIBGSJNGJE-UHFFFAOYSA-N 0.000 description 1
- DBOVJGUOYLNYIP-UHFFFAOYSA-N 5-(2-bromoethoxy)-2-chloro-1,3-dimethylbenzene Chemical compound CC1=CC(OCCBr)=CC(C)=C1Cl DBOVJGUOYLNYIP-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 241000272517 Anseriformes Species 0.000 description 1
- 206010070840 Gastrointestinal tract irritation Diseases 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 208000006550 Mydriasis Diseases 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 1
- 241000244206 Nematoda Species 0.000 description 1
- 241000718543 Ormosia krugii Species 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 1
- QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-N 0.000 description 1
- FMOFKPKVBJKTRN-UHFFFAOYSA-N S(=O)(=O)(O)O.BrC1=CC=C(OCCNC(=N)N)C=C1 Chemical compound S(=O)(=O)(O)O.BrC1=CC=C(OCCNC(=N)N)C=C1 FMOFKPKVBJKTRN-UHFFFAOYSA-N 0.000 description 1
- NLXBLJZNFMEUJM-UHFFFAOYSA-N S(=O)(=O)(O)O.ClC1=C(OCCNC(=N)N)C=CC(=C1)Cl Chemical compound S(=O)(=O)(O)O.ClC1=C(OCCNC(=N)N)C=CC(=C1)Cl NLXBLJZNFMEUJM-UHFFFAOYSA-N 0.000 description 1
- HATDLKUSJKUVDP-UHFFFAOYSA-N S(=O)(=O)(O)O.ClC1=CC(=C(OCCNC(=N)N)C=C1)C Chemical compound S(=O)(=O)(O)O.ClC1=CC(=C(OCCNC(=N)N)C=C1)C HATDLKUSJKUVDP-UHFFFAOYSA-N 0.000 description 1
- FSTQOZGXFYCNSV-UHFFFAOYSA-N S(=O)(=O)(O)O.ClC=1C=C(OCCNC(=N)N)C=CC1C Chemical compound S(=O)(=O)(O)O.ClC=1C=C(OCCNC(=N)N)C=CC1C FSTQOZGXFYCNSV-UHFFFAOYSA-N 0.000 description 1
- 229910021607 Silver chloride Inorganic materials 0.000 description 1
- 241000731783 Strongyloides papillosus Species 0.000 description 1
- 241000244177 Strongyloides stercoralis Species 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000001800 adrenalinergic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 230000003542 behavioural effect Effects 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229960002624 bretylium tosilate Drugs 0.000 description 1
- 229960004895 bretylium tosylate Drugs 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 229960002242 chlorocresol Drugs 0.000 description 1
- 239000000812 cholinergic antagonist Substances 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid group Chemical group C(CC(O)(C(=O)O)CC(=O)O)(=O)O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- 230000010339 dilation Effects 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- MNQDKWZEUULFPX-UHFFFAOYSA-M dithiazanine iodide Chemical compound [I-].S1C2=CC=CC=C2[N+](CC)=C1C=CC=CC=C1N(CC)C2=CC=CC=C2S1 MNQDKWZEUULFPX-UHFFFAOYSA-M 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- ARFLASKVLJTEJD-UHFFFAOYSA-N ethyl 2-bromopropanoate Chemical compound CCOC(=O)C(C)Br ARFLASKVLJTEJD-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 210000000744 eyelid Anatomy 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000013505 freshwater Substances 0.000 description 1
- 239000003457 ganglion blocking agent Substances 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 150000002357 guanidines Chemical class 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 150000002689 maleic acids Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000012457 nonaqueous media Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- XULSCZPZVQIMFM-IPZQJPLYSA-N odevixibat Chemical compound C12=CC(SC)=C(OCC(=O)N[C@@H](C(=O)N[C@@H](CC)C(O)=O)C=3C=CC(O)=CC=3)C=C2S(=O)(=O)NC(CCCC)(CCCC)CN1C1=CC=CC=C1 XULSCZPZVQIMFM-IPZQJPLYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000001734 parasympathetic effect Effects 0.000 description 1
- 230000002445 parasympatholytic effect Effects 0.000 description 1
- 230000001499 parasympathomimetic effect Effects 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- OLBCVFGFOZPWHH-UHFFFAOYSA-N propofol Chemical compound CC(C)C1=CC=CC(C(C)C)=C1O OLBCVFGFOZPWHH-UHFFFAOYSA-N 0.000 description 1
- 210000001747 pupil Anatomy 0.000 description 1
- BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 1
- 229960003147 reserpine Drugs 0.000 description 1
- MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 1
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 1
- 235000011069 sorbitan monooleate Nutrition 0.000 description 1
- 239000001593 sorbitan monooleate Substances 0.000 description 1
- 229940035049 sorbitan monooleate Drugs 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000002889 sympathetic effect Effects 0.000 description 1
- 210000002820 sympathetic nervous system Anatomy 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/58—Preparation of carboxylic acid halides
- C07C51/60—Preparation of carboxylic acid halides by conversion of carboxylic acids or their anhydrides or esters, lactones, salts into halides with the same carboxylic acid part
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7627/60A GB993581A (en) | 1960-03-03 | 1960-03-03 | Phenoxyalkylguanidines and their synthesis and pharmaceutical preparations containing them |
| GB3513460 | 1960-10-13 | ||
| GB247561 | 1961-01-20 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1443216A1 DE1443216A1 (de) | 1969-11-27 |
| DE1443216B2 DE1443216B2 (de) | 1973-02-15 |
| DE1443216C3 true DE1443216C3 (de) | 1973-09-13 |
Family
ID=27254076
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1443216A Expired DE1443216C3 (de) | 1960-03-03 | 1961-03-02 | Verfahren zur Herstellung von Phenoxyalkylguanidinen und solche Verbindungen enthaltende Arzneimittel |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3099599A (enExample) |
| CH (1) | CH429694A (enExample) |
| DE (1) | DE1443216C3 (enExample) |
| DK (1) | DK111564B (enExample) |
| FR (1) | FR1305369A (enExample) |
| GB (1) | GB993581A (enExample) |
| SE (1) | SE308102B (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL295240A (enExample) * | 1963-02-05 | |||
| US3255249A (en) * | 1963-04-26 | 1966-06-07 | Ici Ltd | 2-branched lower alkyl-amino-1-(indan-, hydrogenated indan- and hydrogenated naphth-2-yl) lower alkanols |
| IL22369A (en) * | 1963-11-19 | 1968-10-24 | Merck & Co Inc | 2-heteroaryl-5 and/or 6-substituted benzazoles |
| US3246031A (en) * | 1965-02-23 | 1966-04-12 | Parke Davis & Co | Phenoxypropylguanidine compounds |
| ZA694133B (en) * | 1968-08-27 | 1971-01-27 | Colgate Palmolive Co | Aryloxyalkylguanidines |
| IE46886B1 (en) * | 1977-05-17 | 1983-10-19 | Allen & Hanburys Ltd | Aminoalkyl-benzene derivatives |
| FR2395983A1 (fr) | 1977-06-29 | 1979-01-26 | Le Hao Dong | Derives de propylamine, leur procede de preparation et leur application en therapeutique |
| TW300883B (enExample) * | 1994-07-26 | 1997-03-21 | Kao Corp | |
| US5877217A (en) * | 1995-12-26 | 1999-03-02 | Alteon Inc. | N-acylaminoalkyl-hydrazinecarboximidamides |
| CN110981832A (zh) * | 2019-11-01 | 2020-04-10 | 山东美泰医药有限公司 | 一种盐酸罗沙替丁醋酸酯的制备方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2663474A (en) * | 1952-11-15 | 1953-12-22 | Edward J Kelly | Outboard motor carrier |
| US2850426A (en) * | 1955-03-16 | 1958-09-02 | Chemo Puro Mfg Corp | Anthelmintic piperazine-phosphoric acid compositions and method of combatting helminth infestations therewith |
| US2959616A (en) * | 1955-09-28 | 1960-11-08 | Ici Ltd | Guanidines |
| US2910403A (en) * | 1956-01-30 | 1959-10-27 | Nat Drug Co | Anti hypertensive compositions comprising 2-methyl-5, 8-dimethoxychromone and acetamides |
| US2890982A (en) * | 1956-10-30 | 1959-06-16 | Norwich Pharma Co | Method of combatting helminthiasis using nitro-furyl-acrylate derivatives |
| US2960439A (en) * | 1957-03-18 | 1960-11-15 | Wisconsin Alumni Res Found | Urea-dextrose composition and method for reducing intracranial pressure |
-
1960
- 1960-03-03 GB GB7627/60A patent/GB993581A/en not_active Expired
-
1961
- 1961-02-14 US US89125A patent/US3099599A/en not_active Expired - Lifetime
- 1961-03-02 DE DE1443216A patent/DE1443216C3/de not_active Expired
- 1961-03-02 DK DK92161AA patent/DK111564B/da unknown
- 1961-03-03 SE SE2248/61A patent/SE308102B/xx unknown
- 1961-03-03 FR FR854528A patent/FR1305369A/fr not_active Expired
- 1961-03-03 CH CH260261A patent/CH429694A/de unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SE308102B (enExample) | 1969-02-03 |
| GB993581A (en) | 1965-05-26 |
| DE1443216A1 (de) | 1969-11-27 |
| DE1443216B2 (de) | 1973-02-15 |
| US3099599A (en) | 1963-07-30 |
| FR1305369A (fr) | 1962-10-05 |
| CH429694A (de) | 1967-02-15 |
| DK111564B (da) | 1968-09-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| SH | Request for examination between 03.10.1968 and 22.04.1971 | ||
| C3 | Grant after two publication steps (3rd publication) |