CH485681A - Verfahren zur Herstellung von schwefelhaltigen Aminen - Google Patents
Verfahren zur Herstellung von schwefelhaltigen AminenInfo
- Publication number
- CH485681A CH485681A CH1710168A CH1710168A CH485681A CH 485681 A CH485681 A CH 485681A CH 1710168 A CH1710168 A CH 1710168A CH 1710168 A CH1710168 A CH 1710168A CH 485681 A CH485681 A CH 485681A
- Authority
- CH
- Switzerland
- Prior art keywords
- acid
- salts
- compounds
- salt
- converted
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 13
- 238000004519 manufacturing process Methods 0.000 title description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 title description 2
- 150000001412 amines Chemical class 0.000 title description 2
- 229910052717 sulfur Inorganic materials 0.000 title description 2
- 239000011593 sulfur Substances 0.000 title description 2
- 150000003839 salts Chemical class 0.000 claims description 21
- 150000001875 compounds Chemical class 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 7
- 125000003277 amino group Chemical group 0.000 claims description 6
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 125000000068 chlorophenyl group Chemical group 0.000 claims 1
- 230000001419 dependent effect Effects 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 239000002253 acid Substances 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- -1 Vinegar Chemical class 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 239000000935 antidepressant agent Substances 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- RHCSKNNOAZULRK-UHFFFAOYSA-N mescaline Chemical compound COC1=CC(CCN)=CC(OC)=C1OC RHCSKNNOAZULRK-UHFFFAOYSA-N 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 230000000638 stimulation Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- 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
- AAWZDTNXLSGCEK-LNVDRNJUSA-N (3r,5r)-1,3,4,5-tetrahydroxycyclohexane-1-carboxylic acid Chemical compound O[C@@H]1CC(O)(C(O)=O)C[C@@H](O)C1O AAWZDTNXLSGCEK-LNVDRNJUSA-N 0.000 description 1
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-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
- HBJGHMRKCVHRRN-UHFFFAOYSA-N 1-(2-methylphenyl)sulfanylpropan-2-amine Chemical compound CC(N)CSC1=CC=CC=C1C HBJGHMRKCVHRRN-UHFFFAOYSA-N 0.000 description 1
- JCYHBVQFOAWROY-UHFFFAOYSA-N 1-chloropropan-2-amine;hydrochloride Chemical compound Cl.CC(N)CCl JCYHBVQFOAWROY-UHFFFAOYSA-N 0.000 description 1
- 125000005273 2-acetoxybenzoic acid group Chemical group 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
- VZXOZSQDJJNBRC-UHFFFAOYSA-N 4-chlorobenzenethiol Chemical compound SC1=CC=C(Cl)C=C1 VZXOZSQDJJNBRC-UHFFFAOYSA-N 0.000 description 1
- 241000282693 Cercopithecidae Species 0.000 description 1
- 244000223760 Cinnamomum zeylanicum Species 0.000 description 1
- 235000005979 Citrus limon Nutrition 0.000 description 1
- 244000131522 Citrus pyriformis Species 0.000 description 1
- AAWZDTNXLSGCEK-UHFFFAOYSA-N Cordycepinsaeure Natural products OC1CC(O)(C(O)=O)CC(O)C1O AAWZDTNXLSGCEK-UHFFFAOYSA-N 0.000 description 1
- 208000020401 Depressive disease Diseases 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
- 241000282326 Felis catus Species 0.000 description 1
- 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 1
- WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 description 1
- 235000011430 Malus pumila Nutrition 0.000 description 1
- 235000015103 Malus silvestris Nutrition 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- AAWZDTNXLSGCEK-ZHQZDSKASA-N Quinic acid Natural products O[C@H]1CC(O)(C(O)=O)C[C@H](O)C1O AAWZDTNXLSGCEK-ZHQZDSKASA-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
- 241000700159 Rattus Species 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
- 244000028419 Styrax benzoin Species 0.000 description 1
- 235000000126 Styrax benzoin Nutrition 0.000 description 1
- 235000008411 Sumatra benzointree Nutrition 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 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
- 239000002269 analeptic agent Substances 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229960002130 benzoin Drugs 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 235000017803 cinnamon Nutrition 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 1
- 229960001270 d- tartaric acid Drugs 0.000 description 1
- MHUWZNTUIIFHAS-CLFAGFIQSA-N dioleoyl phosphatidic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(COP(O)(O)=O)OC(=O)CCCCCCC\C=C/CCCCCCCC MHUWZNTUIIFHAS-CLFAGFIQSA-N 0.000 description 1
- 208000024732 dysthymic disease Diseases 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 230000002631 hypothermal effect Effects 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- TWBYWOBDOCUKOW-UHFFFAOYSA-N isonicotinic acid Chemical class OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-N 0.000 description 1
- 229960004502 levodopa Drugs 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 208000024714 major depressive disease Diseases 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
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000037023 motor activity Effects 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- KLHRXNDEAPDDME-UHFFFAOYSA-N n-[1-(4-chlorophenyl)propan-2-yl]thiohydroxylamine Chemical group SNC(C)CC1=CC=C(Cl)C=C1 KLHRXNDEAPDDME-UHFFFAOYSA-N 0.000 description 1
- KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 1
- 208000025319 neurotic depression Diseases 0.000 description 1
- 208000015238 neurotic disease Diseases 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000011514 reflex Effects 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
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 229960001367 tartaric acid Drugs 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000014101 wine Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1710168A CH485681A (de) | 1966-06-03 | 1966-06-03 | Verfahren zur Herstellung von schwefelhaltigen Aminen |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH808466A CH480304A (de) | 1966-06-03 | 1966-06-03 | Verfahren zur Herstellung von schwefelhaltigen Aminen |
| CH1710168A CH485681A (de) | 1966-06-03 | 1966-06-03 | Verfahren zur Herstellung von schwefelhaltigen Aminen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH485681A true CH485681A (de) | 1970-02-15 |
Family
ID=4334901
Family Applications (7)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1710168A CH485681A (de) | 1966-06-03 | 1966-06-03 | Verfahren zur Herstellung von schwefelhaltigen Aminen |
| CH1709968A CH480305A (de) | 1966-06-03 | 1966-06-03 | Verfahren zur Herstellung von schwefelhaltigen Aminen |
| CH1710468A CH480307A (de) | 1966-06-03 | 1966-06-03 | Verfahren zur Herstellung von schwefelhaltigen Aminen |
| CH1710068A CH485680A (de) | 1966-06-03 | 1966-06-03 | Verfahren zur Herstellung von schwefelhaltigen Aminen |
| CH1710268A CH485682A (de) | 1966-06-03 | 1966-06-03 | Verfahren zur Herstellung von schwefelhaltigen Aminen |
| CH1710368A CH480306A (de) | 1966-06-03 | 1966-06-03 | Verfahren zur Herstellung von schwefelhaltigen Aminen |
| CH808466A CH480304A (de) | 1966-06-03 | 1966-06-03 | Verfahren zur Herstellung von schwefelhaltigen Aminen |
Family Applications After (6)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1709968A CH480305A (de) | 1966-06-03 | 1966-06-03 | Verfahren zur Herstellung von schwefelhaltigen Aminen |
| CH1710468A CH480307A (de) | 1966-06-03 | 1966-06-03 | Verfahren zur Herstellung von schwefelhaltigen Aminen |
| CH1710068A CH485680A (de) | 1966-06-03 | 1966-06-03 | Verfahren zur Herstellung von schwefelhaltigen Aminen |
| CH1710268A CH485682A (de) | 1966-06-03 | 1966-06-03 | Verfahren zur Herstellung von schwefelhaltigen Aminen |
| CH1710368A CH480306A (de) | 1966-06-03 | 1966-06-03 | Verfahren zur Herstellung von schwefelhaltigen Aminen |
| CH808466A CH480304A (de) | 1966-06-03 | 1966-06-03 | Verfahren zur Herstellung von schwefelhaltigen Aminen |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3519686A (ref) |
| AT (7) | AT282584B (ref) |
| BE (1) | BE699290A (ref) |
| CH (7) | CH485681A (ref) |
| DE (1) | DE1593800A1 (ref) |
| FR (1) | FR6474M (ref) |
| GB (1) | GB1155549A (ref) |
| NL (1) | NL6707726A (ref) |
| SE (1) | SE330028B (ref) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3884951A (en) * | 1968-09-11 | 1975-05-20 | Exxon Research Engineering Co | Thioether isocyanate adducts |
| US3998866A (en) * | 1971-01-18 | 1976-12-21 | Exxon Research And Engineering Company | Thioether propyl isocyanates |
| US4558071A (en) * | 1979-08-15 | 1985-12-10 | Merck & Co., Inc. | Phenyl, trihalomethyl or heteroaryl sulfoxides having a latent allyl group bound to sulfur as enzyme inhibitors |
| US4760067A (en) * | 1979-08-15 | 1988-07-26 | Merck & Co., Inc. | Allylsulfoxide enzyme inhibitors |
| US4388475A (en) * | 1979-08-15 | 1983-06-14 | Merck & Co., Inc. | Allylsulfoxide enzyme inhibitors |
| EP0053015A1 (en) * | 1980-11-21 | 1982-06-02 | Takeda Chemical Industries, Ltd. | 1-Phenylthio-2-aminopropane derivatives, their production and use |
| US4415591A (en) * | 1981-06-04 | 1983-11-15 | Georgia Tech Research Institute | Use of aminoalkyl phenyl sulfide derivatives for the treatment of hypertension |
| ZA855101B (en) * | 1984-07-13 | 1986-05-28 | Merrell Dow Pharma | Fluoroallylaine derivatives |
| US5841589A (en) * | 1995-09-26 | 1998-11-24 | Boeing North American, Inc. | Panoramic optics assembly having an initial flat reflective element |
| CA2259922C (en) * | 1996-07-08 | 2009-04-28 | Kirin Beer Kabushiki Kaisha | Calcium receptor active compounds |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2769839A (en) * | 1950-06-23 | 1956-11-06 | Monsanto Chemicals | Preparation of mercapto amines |
| GB1027611A (en) * | 1962-01-04 | 1966-04-27 | May & Baker Ltd | Phenoxy- and phenylthio-alkylamines and acid addition salts thereof |
| US3156725A (en) * | 1962-04-18 | 1964-11-10 | Smith Kline French Lab | Substituted 2-phenoxy and phenylthio-cyclopropylamines |
| US3235597A (en) * | 1963-08-12 | 1966-02-15 | Lilly Co Eli | N-aryloxyalkyl and arylthioalkyl derivatives of cyclopropylamine |
| BE653101A (ref) * | 1964-09-15 | 1964-12-31 |
-
1966
- 1966-06-03 CH CH1710168A patent/CH485681A/de not_active IP Right Cessation
- 1966-06-03 CH CH1709968A patent/CH480305A/de not_active IP Right Cessation
- 1966-06-03 CH CH1710468A patent/CH480307A/de not_active IP Right Cessation
- 1966-06-03 CH CH1710068A patent/CH485680A/de not_active IP Right Cessation
- 1966-06-03 CH CH1710268A patent/CH485682A/de not_active IP Right Cessation
- 1966-06-03 CH CH1710368A patent/CH480306A/de not_active IP Right Cessation
- 1966-06-03 CH CH808466A patent/CH480304A/de not_active IP Right Cessation
-
1967
- 1967-05-23 US US640494A patent/US3519686A/en not_active Expired - Lifetime
- 1967-05-25 GB GB24329/67A patent/GB1155549A/en not_active Expired
- 1967-05-26 DE DE19671593800 patent/DE1593800A1/de active Pending
- 1967-05-30 FR FR108388A patent/FR6474M/fr not_active Expired
- 1967-05-31 BE BE699290D patent/BE699290A/xx unknown
- 1967-06-02 AT AT12543/68A patent/AT282584B/de not_active IP Right Cessation
- 1967-06-02 AT AT12545/68A patent/AT280242B/de not_active IP Right Cessation
- 1967-06-02 AT AT514167A patent/AT276355B/de active
- 1967-06-02 SE SE07737/67A patent/SE330028B/xx unknown
- 1967-06-02 AT AT12539/68A patent/AT280239B/de not_active IP Right Cessation
- 1967-06-02 AT AT12542/68A patent/AT282583B/de active
- 1967-06-02 AT AT12541/68A patent/AT280241B/de not_active IP Right Cessation
- 1967-06-02 AT AT12540/68A patent/AT280240B/de not_active IP Right Cessation
- 1967-06-02 NL NL6707726A patent/NL6707726A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CH485680A (de) | 1970-02-15 |
| AT280239B (de) | 1970-04-10 |
| US3519686A (en) | 1970-07-07 |
| SE330028B (ref) | 1970-11-02 |
| CH480305A (de) | 1969-10-31 |
| NL6707726A (ref) | 1967-12-04 |
| FR6474M (ref) | 1968-11-18 |
| AT276355B (de) | 1969-11-25 |
| AT282584B (de) | 1970-07-10 |
| CH480304A (de) | 1969-10-31 |
| CH485682A (de) | 1970-02-15 |
| AT280242B (de) | 1970-04-10 |
| AT280241B (de) | 1970-04-10 |
| AT282583B (de) | 1970-07-10 |
| CH480307A (de) | 1969-10-31 |
| GB1155549A (en) | 1969-06-18 |
| CH480306A (de) | 1969-10-31 |
| DE1593800A1 (de) | 1970-10-29 |
| BE699290A (ref) | 1967-11-30 |
| AT280240B (de) | 1970-04-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |