DE1128856B - Verfahren zur Herstellung von in 3-Stellung durch schwefelhaltige Gruppen substituierten Phenthiazinderivaten - Google Patents
Verfahren zur Herstellung von in 3-Stellung durch schwefelhaltige Gruppen substituierten PhenthiazinderivatenInfo
- Publication number
- DE1128856B DE1128856B DE1957S0052942 DES0052942A DE1128856B DE 1128856 B DE1128856 B DE 1128856B DE 1957S0052942 DE1957S0052942 DE 1957S0052942 DE S0052942 A DES0052942 A DE S0052942A DE 1128856 B DE1128856 B DE 1128856B
- Authority
- DE
- Germany
- Prior art keywords
- ecm
- phenthiazine
- solution
- hours
- benzene
- 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.)
- Pending
Links
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical group C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 title claims description 19
- 238000000034 method Methods 0.000 title claims description 12
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 title claims description 11
- 239000011593 sulfur Substances 0.000 title claims description 11
- 229910052717 sulfur Inorganic materials 0.000 title claims description 11
- 238000002360 preparation method Methods 0.000 title description 8
- -1 benzyl mercapto group Chemical group 0.000 claims description 22
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 239000000460 chlorine Substances 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 183
- 239000000243 solution Substances 0.000 description 88
- XEKOWRVHYACXOJ-UHFFFAOYSA-N ethyl acetate Substances CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 67
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 59
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 56
- 239000008096 xylene Substances 0.000 description 56
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 52
- 238000010438 heat treatment Methods 0.000 description 42
- 239000002585 base Substances 0.000 description 40
- 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 35
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 35
- 229910052753 mercury Inorganic materials 0.000 description 35
- 235000002906 tartaric acid Nutrition 0.000 description 35
- 239000011975 tartaric acid Substances 0.000 description 35
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 34
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 34
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 33
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 25
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 24
- 239000000284 extract Substances 0.000 description 24
- 230000000694 effects Effects 0.000 description 23
- 239000011541 reaction mixture Substances 0.000 description 23
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
- 238000001704 evaporation Methods 0.000 description 21
- 230000008020 evaporation Effects 0.000 description 21
- 239000000126 substance Substances 0.000 description 21
- 238000009835 boiling Methods 0.000 description 20
- 238000003756 stirring Methods 0.000 description 20
- 229940072033 potash Drugs 0.000 description 19
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 19
- 235000015320 potassium carbonate Nutrition 0.000 description 19
- 235000011121 sodium hydroxide Nutrition 0.000 description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 18
- 238000010992 reflux Methods 0.000 description 18
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 18
- 235000019270 ammonium chloride Nutrition 0.000 description 17
- 229960005382 phenolphthalein Drugs 0.000 description 17
- 229940095064 tartrate Drugs 0.000 description 17
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 16
- 238000005245 sintering Methods 0.000 description 14
- 241001465754 Metazoa Species 0.000 description 13
- 239000012458 free base Substances 0.000 description 13
- 235000002639 sodium chloride Nutrition 0.000 description 13
- 150000003839 salts Chemical class 0.000 description 12
- 230000002996 emotional effect Effects 0.000 description 10
- 230000013872 defecation Effects 0.000 description 9
- 239000000155 melt Substances 0.000 description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 8
- 230000002903 catalepsic effect Effects 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 8
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 7
- 208000009132 Catalepsy Diseases 0.000 description 7
- 206010047853 Waxy flexibility Diseases 0.000 description 7
- 239000013078 crystal Substances 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- 229910052740 iodine Inorganic materials 0.000 description 7
- 239000011630 iodine Substances 0.000 description 7
- 239000003208 petroleum Substances 0.000 description 7
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 7
- 230000009183 running Effects 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 241000700159 Rattus Species 0.000 description 6
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 6
- 229960003750 ethyl chloride Drugs 0.000 description 6
- 230000002401 inhibitory effect Effects 0.000 description 6
- 230000005764 inhibitory process Effects 0.000 description 6
- 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 6
- KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 description 5
- 229940025084 amphetamine Drugs 0.000 description 5
- 238000000354 decomposition reaction Methods 0.000 description 5
- 230000005284 excitation Effects 0.000 description 5
- 230000037023 motor activity Effects 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- IKCLCGXPQILATA-UHFFFAOYSA-N 2-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1Cl IKCLCGXPQILATA-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 208000010513 Stupor Diseases 0.000 description 4
- UCTWMZQNUQWSLP-UHFFFAOYSA-N adrenaline Chemical compound CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 description 4
- 230000002908 adrenolytic effect Effects 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 230000001143 conditioned effect Effects 0.000 description 4
- HESHRHUZIWVEAJ-JGRZULCMSA-N dihydroergotamine Chemical compound C([C@H]1C(=O)N2CCC[C@H]2[C@]2(O)O[C@@](C(N21)=O)(C)NC(=O)[C@H]1CN([C@H]2[C@@H](C3=CC=CC4=NC=C([C]34)C2)C1)C)C1=CC=CC=C1 HESHRHUZIWVEAJ-JGRZULCMSA-N 0.000 description 4
- 229960004704 dihydroergotamine Drugs 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- 231100000419 toxicity Toxicity 0.000 description 4
- 230000001988 toxicity Effects 0.000 description 4
- 206010002091 Anaesthesia Diseases 0.000 description 3
- 239000005711 Benzoic acid Substances 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000002159 abnormal effect Effects 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000037005 anaesthesia Effects 0.000 description 3
- 230000000843 anti-fungal effect Effects 0.000 description 3
- 235000010233 benzoic acid Nutrition 0.000 description 3
- 229940095731 candida albicans Drugs 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 230000000855 fungicidal effect Effects 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 2
- AGIJRRREJXSQJR-UHFFFAOYSA-N 2h-thiazine Chemical compound N1SC=CC=C1 AGIJRRREJXSQJR-UHFFFAOYSA-N 0.000 description 2
- NYYRRBOMNHUCLB-UHFFFAOYSA-N 3-chloro-n,n-dimethylpropan-1-amine Chemical compound CN(C)CCCCl NYYRRBOMNHUCLB-UHFFFAOYSA-N 0.000 description 2
- 241000222122 Candida albicans Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 244000248349 Citrus limon Species 0.000 description 2
- 235000005979 Citrus limon Nutrition 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000004414 alkyl thio group Chemical group 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 230000003444 anaesthetic effect Effects 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
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- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
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- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
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- WRFYXBKJHZAUTO-UHFFFAOYSA-N 1-nitro-2-propan-2-ylsulfanylbenzene Chemical compound CC(C)SC1=CC=CC=C1[N+]([O-])=O WRFYXBKJHZAUTO-UHFFFAOYSA-N 0.000 description 1
- GHQFLMULNSGOAR-UHFFFAOYSA-N 2,3-dihydroxybutanedioic acid;sodium Chemical compound [Na].OC(=O)C(O)C(O)C(O)=O GHQFLMULNSGOAR-UHFFFAOYSA-N 0.000 description 1
- JLVZKULKBLUFIY-UHFFFAOYSA-N 2-(3-methylsulfanylanilino)benzoic acid Chemical compound CSC1=CC=CC(NC=2C(=CC=CC=2)C(O)=O)=C1 JLVZKULKBLUFIY-UHFFFAOYSA-N 0.000 description 1
- RMMIRCPZDWCSMD-UHFFFAOYSA-N 2-(3-propan-2-ylsulfanylanilino)benzoic acid Chemical compound C(C)(C)SC=1C=C(C=CC1)NC=1C(C(=O)O)=CC=CC1 RMMIRCPZDWCSMD-UHFFFAOYSA-N 0.000 description 1
- BZPGKPLLPRDLTC-UHFFFAOYSA-N 3-(2-methylpropylsulfanyl)-N-phenylaniline Chemical compound C(C(C)C)SC=1C=C(C=CC1)NC1=CC=CC=C1 BZPGKPLLPRDLTC-UHFFFAOYSA-N 0.000 description 1
- GKLFDWGXDPXYFM-UHFFFAOYSA-N 3-benzylsulfanyl-N-phenylaniline Chemical compound C(SC1=CC=CC(NC2=CC=CC=C2)=C1)C1=CC=CC=C1 GKLFDWGXDPXYFM-UHFFFAOYSA-N 0.000 description 1
- NGTRZJDYCCOXBA-UHFFFAOYSA-N 3-methylsulfanyl-n-phenylaniline Chemical compound CSC1=CC=CC(NC=2C=CC=CC=2)=C1 NGTRZJDYCCOXBA-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
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- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
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- 239000008103 glucose Substances 0.000 description 1
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- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910000103 lithium hydride Inorganic materials 0.000 description 1
- SIAPCJWMELPYOE-UHFFFAOYSA-N lithium hydride Chemical compound [LiH] SIAPCJWMELPYOE-UHFFFAOYSA-N 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
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- KQGRMKLYONINOY-UHFFFAOYSA-N n-(3-methylphenyl)thiohydroxylamine Chemical compound CC1=CC=CC(NS)=C1 KQGRMKLYONINOY-UHFFFAOYSA-N 0.000 description 1
- SNMVRZFUUCLYTO-UHFFFAOYSA-N n-propyl chloride Chemical compound CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000003176 neuroleptic agent Substances 0.000 description 1
- 230000000701 neuroleptic effect Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 125000005936 piperidyl group Chemical group 0.000 description 1
- 230000003334 potential effect Effects 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 210000001625 seminal vesicle Anatomy 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229940056910 silver sulfide Drugs 0.000 description 1
- XUARKZBEFFVFRG-UHFFFAOYSA-N silver sulfide Chemical compound [S-2].[Ag+].[Ag+] XUARKZBEFFVFRG-UHFFFAOYSA-N 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000000935 solvent evaporation Methods 0.000 description 1
- 230000002048 spasmolytic effect Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000004354 sulfur functional group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 229940098465 tincture Drugs 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 201000010653 vesiculitis Diseases 0.000 description 1
- 238000004804 winding Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D279/04—1,3-Thiazines; Hydrogenated 1,3-thiazines
- C07D279/08—1,3-Thiazines; Hydrogenated 1,3-thiazines condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D279/10—1,4-Thiazines; Hydrogenated 1,4-thiazines
- C07D279/14—1,4-Thiazines; Hydrogenated 1,4-thiazines condensed with carbocyclic rings or ring systems
- C07D279/18—[b, e]-condensed with two six-membered rings
- C07D279/22—[b, e]-condensed with two six-membered rings with carbon atoms directly attached to the ring nitrogen atom
- C07D279/24—[b, e]-condensed with two six-membered rings with carbon atoms directly attached to the ring nitrogen atom with hydrocarbon radicals, substituted by amino radicals, attached to the ring nitrogen atom
- C07D279/28—[b, e]-condensed with two six-membered rings with carbon atoms directly attached to the ring nitrogen atom with hydrocarbon radicals, substituted by amino radicals, attached to the ring nitrogen atom with other substituents attached to the ring system
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0025—Crosslinking or vulcanising agents; including accelerators
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
- C10M135/32—Heterocyclic sulfur, selenium or tellurium compounds
- C10M135/36—Heterocyclic sulfur, selenium or tellurium compounds the ring containing sulfur and carbon with nitrogen or oxygen
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
- H01G9/00—Electrolytic capacitors, rectifiers, detectors, switching devices, light-sensitive or temperature-sensitive devices; Processes of their manufacture
- H01G9/004—Details
- H01G9/08—Housing; Encapsulation
- H01G9/10—Sealing, e.g. of lead-in wires
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
- C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
- C10M2219/108—Phenothiazine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Power Engineering (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- General Chemical & Material Sciences (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Polymers & Plastics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH3228356A CH365379A (de) | 1956-04-18 | 1956-04-18 | Verfahren zur Herstellung von neuen, in 3-Stellung mit einer einwertigen Schwefelfunktion substituierten Phenothiazinen |
| CH4301757A CH364782A (de) | 1957-02-22 | 1957-02-22 | Verfahren zur Herstellung von 3-Sulfhydryl-10-(2'-(N-methyl-piperidyl-2'')-äthyl-1')-phenothiazin |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1128856B true DE1128856B (de) | 1962-05-03 |
Family
ID=25736343
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1957S0052942 Pending DE1128856B (de) | 1956-04-18 | 1957-03-29 | Verfahren zur Herstellung von in 3-Stellung durch schwefelhaltige Gruppen substituierten Phenthiazinderivaten |
| DE1958S0057244 Pending DE1090667B (de) | 1956-04-18 | 1958-03-07 | Verfahren zur Herstellung von basischen Phenthiazinderivaten |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1958S0057244 Pending DE1090667B (de) | 1956-04-18 | 1958-03-07 | Verfahren zur Herstellung von basischen Phenthiazinderivaten |
Country Status (7)
| Country | Link |
|---|---|
| BE (2) | BE556725A (OSRAM) |
| CH (2) | CH365379A (OSRAM) |
| CY (1) | CY275A (OSRAM) |
| DE (2) | DE1128856B (OSRAM) |
| FR (2) | FR1174268A (OSRAM) |
| GB (3) | GB863547A (OSRAM) |
| NL (3) | NL105268C (OSRAM) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE635096A (OSRAM) * | 1962-07-19 | |||
| CH457442A (de) * | 1965-01-12 | 1968-06-15 | Sandoz Ag | Verfahren zur Herstellung neuer Phenothiazin-Derivate |
| IT1237209B (it) * | 1989-12-21 | 1993-05-27 | Zambon Spa | Processo per la funzionalizzazione diretta e regioselettiva in posizione 2 della fenotiazina |
| JP2003519693A (ja) | 2000-01-07 | 2003-06-24 | ワーナー−ランバート・カンパニー、リミテッド、ライアビリティ、カンパニー | 三環式化合物及びヘルペスウイルスを処置する方法 |
| DE102010062810B4 (de) * | 2010-09-07 | 2014-03-13 | Immungenetics Ag | 2-(R2-Thio)-10-[3-(4-R1-piperazin-1-yl)propyl]-10H-phenothiazine zur Behandlung neurodegenerativer Erkrankungen ausgewählt aus beta-Amyloidopathien und alpha-Synucleinopathien |
| EP3116495B1 (en) * | 2014-03-10 | 2019-11-06 | Université d'Aix-Marseille | Piperazine phenothiazine derivatives for treating spasticity |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE910301C (de) * | 1950-12-21 | 1954-04-29 | Rhone Poulenc Sa | Verfahren zur Herstellung von neuen Phenthiazinderivaten |
| CH298685A (fr) * | 1951-06-28 | 1954-05-15 | Rhone Poulenc Chemicals | Procédé de préparation d'un nouveau dérivé de la phénothiazine. |
| DE1058998B (de) | 1955-11-25 | 1959-06-11 | Rhone Poulenc Sa | Verfahren zur Herstellung von Phenthiazinderivaten |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE939630C (de) * | 1953-10-25 | 1956-03-01 | Basf Ag | Verfahren zur Herstellung von heterocyclischen Verbindungen mit ringstaendiger Iminogruppe, die durch basische Gruppen substituiert ist |
| BE558008A (OSRAM) * | 1956-06-21 |
-
1956
- 1956-04-18 CH CH3228356A patent/CH365379A/de unknown
- 1956-04-19 CH CH360059D patent/CH360059A/de unknown
-
1957
- 1957-03-29 DE DE1957S0052942 patent/DE1128856B/de active Pending
- 1957-04-04 GB GB1105057A patent/GB863547A/en not_active Expired
- 1957-04-04 GB GB1738060A patent/GB863550A/en not_active Expired
- 1957-04-16 BE BE556725A patent/BE556725A/xx unknown
- 1957-04-17 FR FR1174268D patent/FR1174268A/fr not_active Expired
- 1957-04-17 NL NL216436A patent/NL105268C/xx active
- 1957-04-17 NL NL216435A patent/NL105267C/xx active
-
1958
- 1958-03-06 BE BE565470A patent/BE565470A/xx unknown
- 1958-03-07 FR FR1203557D patent/FR1203557A/fr not_active Expired
- 1958-03-07 NL NL225621A patent/NL108580C/xx active
- 1958-03-07 DE DE1958S0057244 patent/DE1090667B/de active Pending
- 1958-03-07 GB GB748158A patent/GB858140A/en not_active Expired
-
1964
- 1964-02-12 CY CY27564A patent/CY275A/xx unknown
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE910301C (de) * | 1950-12-21 | 1954-04-29 | Rhone Poulenc Sa | Verfahren zur Herstellung von neuen Phenthiazinderivaten |
| CH298685A (fr) * | 1951-06-28 | 1954-05-15 | Rhone Poulenc Chemicals | Procédé de préparation d'un nouveau dérivé de la phénothiazine. |
| DE1058998B (de) | 1955-11-25 | 1959-06-11 | Rhone Poulenc Sa | Verfahren zur Herstellung von Phenthiazinderivaten |
Also Published As
| Publication number | Publication date |
|---|---|
| CY275A (en) | 1964-02-12 |
| NL105267C (OSRAM) | 1963-07-15 |
| GB863550A (en) | 1961-03-22 |
| BE556725A (OSRAM) | 1957-10-16 |
| FR1174268A (fr) | 1959-03-09 |
| CH360059A (de) | 1962-02-15 |
| GB863547A (en) | 1961-03-22 |
| FR1203557A (fr) | 1960-01-20 |
| CH365379A (de) | 1962-11-15 |
| GB858140A (en) | 1961-01-04 |
| BE565470A (OSRAM) | 1958-09-06 |
| NL108580C (OSRAM) | 1964-06-15 |
| NL105268C (OSRAM) | 1963-07-15 |
| DE1090667B (de) | 1960-10-13 |
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