CH365379A - Verfahren zur Herstellung von neuen, in 3-Stellung mit einer einwertigen Schwefelfunktion substituierten Phenothiazinen - Google Patents
Verfahren zur Herstellung von neuen, in 3-Stellung mit einer einwertigen Schwefelfunktion substituierten PhenothiazinenInfo
- Publication number
- CH365379A CH365379A CH3228356A CH3228356A CH365379A CH 365379 A CH365379 A CH 365379A CH 3228356 A CH3228356 A CH 3228356A CH 3228356 A CH3228356 A CH 3228356A CH 365379 A CH365379 A CH 365379A
- Authority
- CH
- Switzerland
- Prior art keywords
- aniline
- phenyl
- sulfur
- phenothiazines
- phenothiazine
- Prior art date
Links
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 title claims description 21
- 238000000034 method Methods 0.000 title claims description 11
- 150000002990 phenothiazines Chemical group 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title description 2
- 239000011593 sulfur Substances 0.000 claims description 13
- 229910052717 sulfur Inorganic materials 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 claims description 4
- YNHGMBTXSRJGLC-UHFFFAOYSA-N 3-ethylsulfanyl-n-phenylaniline Chemical compound CCSC1=CC=CC(NC=2C=CC=CC=2)=C1 YNHGMBTXSRJGLC-UHFFFAOYSA-N 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 33
- 238000002844 melting Methods 0.000 description 15
- 230000008018 melting Effects 0.000 description 15
- -1 3-n-Propylmercapto-phenothiazine Chemical compound 0.000 description 10
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 10
- 238000010438 heat treatment Methods 0.000 description 10
- 229910052740 iodine Inorganic materials 0.000 description 10
- 239000011630 iodine Substances 0.000 description 10
- IKCLCGXPQILATA-UHFFFAOYSA-N 2-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1Cl IKCLCGXPQILATA-UHFFFAOYSA-N 0.000 description 9
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 9
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 9
- 239000007858 starting material Substances 0.000 description 9
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 8
- 239000003208 petroleum Substances 0.000 description 8
- 238000004821 distillation Methods 0.000 description 7
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 229950000688 phenothiazine Drugs 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 3
- 239000003610 charcoal Substances 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000000126 substance 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
- LEUKPJKOYBCWGE-UHFFFAOYSA-N 3-butylsulfanyl-N-phenylaniline Chemical compound C(CCC)SC=1C=C(C=CC1)NC1=CC=CC=C1 LEUKPJKOYBCWGE-UHFFFAOYSA-N 0.000 description 2
- KBHBUAAMEHPZKQ-UHFFFAOYSA-N 3-ethylsulfanyl-10H-phenothiazine Chemical compound CCSC1=CC=C2NC3=CC=CC=C3SC2=C1 KBHBUAAMEHPZKQ-UHFFFAOYSA-N 0.000 description 2
- MRYWSLAXVVHDBL-UHFFFAOYSA-N 3-iodo-n-phenylaniline Chemical compound IC1=CC=CC(NC=2C=CC=CC=2)=C1 MRYWSLAXVVHDBL-UHFFFAOYSA-N 0.000 description 2
- JZROAVSLDUAQEI-UHFFFAOYSA-N 3-methylsulfanyl-10H-phenothiazine Chemical compound C1=CC=C2SC3=CC(SC)=CC=C3NC2=C1 JZROAVSLDUAQEI-UHFFFAOYSA-N 0.000 description 2
- NGTRZJDYCCOXBA-UHFFFAOYSA-N 3-methylsulfanyl-n-phenylaniline Chemical compound CSC1=CC=CC(NC=2C=CC=CC=2)=C1 NGTRZJDYCCOXBA-UHFFFAOYSA-N 0.000 description 2
- JHFFHPJYSOCGEG-UHFFFAOYSA-N 3-propan-2-yl-10H-phenothiazine-1-thiol Chemical compound C(C)(C)C=1C=C(C=2NC3=CC=CC=C3SC=2C=1)S JHFFHPJYSOCGEG-UHFFFAOYSA-N 0.000 description 2
- NDJOOOBYISLBRN-UHFFFAOYSA-N N-phenyl-3-phenylsulfanylaniline Chemical compound C1(=CC=CC=C1)SC=1C=C(C=CC=1)NC1=CC=CC=C1 NDJOOOBYISLBRN-UHFFFAOYSA-N 0.000 description 2
- DBVMVLJJUKDKPU-UHFFFAOYSA-N N-phenyl-3-propan-2-ylsulfanylaniline Chemical compound CC(C)SC1=CC=CC(NC2=CC=CC=C2)=C1 DBVMVLJJUKDKPU-UHFFFAOYSA-N 0.000 description 2
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 2
- QFFVPLLCYGOFPU-UHFFFAOYSA-N barium chromate Chemical compound [Ba+2].[O-][Cr]([O-])(=O)=O QFFVPLLCYGOFPU-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000001119 stannous chloride Substances 0.000 description 2
- 235000011150 stannous chloride Nutrition 0.000 description 2
- XXBJOUVPMYFEMP-UHFFFAOYSA-N 1-nitro-3-propan-2-ylsulfanylbenzene Chemical compound CC(C)SC1=CC=CC([N+]([O-])=O)=C1 XXBJOUVPMYFEMP-UHFFFAOYSA-N 0.000 description 1
- IDXNHZYYCSONAN-UHFFFAOYSA-N 10h-phenothiazine-1-thiol Chemical class S1C2=CC=CC=C2NC2=C1C=CC=C2S IDXNHZYYCSONAN-UHFFFAOYSA-N 0.000 description 1
- ISVGOYORMPENJM-UHFFFAOYSA-N 2-(3-benzylsulfanylanilino)benzoic acid Chemical compound C(C1=CC=CC=C1)SC=1C=C(C=CC1)NC=1C(C(=O)O)=CC=CC1 ISVGOYORMPENJM-UHFFFAOYSA-N 0.000 description 1
- LIWNFNNKPBGCFM-UHFFFAOYSA-N 2-(3-ethylsulfanylanilino)benzoic acid Chemical compound CCSC1=CC=CC(NC=2C(=CC=CC=2)C(O)=O)=C1 LIWNFNNKPBGCFM-UHFFFAOYSA-N 0.000 description 1
- YDHVAPBSJDSJRG-UHFFFAOYSA-N 2-(3-iodoanilino)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1NC1=CC=CC(I)=C1 YDHVAPBSJDSJRG-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
- QORUUPHJNPXGEN-UHFFFAOYSA-N 2-anilino-6-benzylbenzenethiol Chemical compound C(C1=CC=CC=C1)C=1C(=C(C=CC1)NC1=CC=CC=C1)S QORUUPHJNPXGEN-UHFFFAOYSA-N 0.000 description 1
- AGIJRRREJXSQJR-UHFFFAOYSA-N 2h-thiazine Chemical group N1SC=CC=C1 AGIJRRREJXSQJR-UHFFFAOYSA-N 0.000 description 1
- NSKBGLNCWALASV-UHFFFAOYSA-N 3-(2-methylpropylsulfanyl)-10H-phenothiazine Chemical compound C(C(C)C)SC=1C=CC=2NC3=CC=CC=C3SC2C1 NSKBGLNCWALASV-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
- XVUKOTZEXLIZIB-UHFFFAOYSA-N 3-benzylsulfanylaniline Chemical compound NC1=CC=CC(SCC=2C=CC=CC=2)=C1 XVUKOTZEXLIZIB-UHFFFAOYSA-N 0.000 description 1
- FFCSRWGYGMRBGD-UHFFFAOYSA-N 3-iodoaniline Chemical compound NC1=CC=CC(I)=C1 FFCSRWGYGMRBGD-UHFFFAOYSA-N 0.000 description 1
- VFBCFRMFVYFAJA-UHFFFAOYSA-N 3-propan-2-ylsulfanyl-10H-phenothiazine Chemical compound C(C)(C)SC=1C=CC=2NC3=CC=CC=C3SC2C1 VFBCFRMFVYFAJA-UHFFFAOYSA-N 0.000 description 1
- PKKKSXIPDFGVKI-UHFFFAOYSA-N CCC1=CC=CC(NS)=C1 Chemical compound CCC1=CC=CC(NS)=C1 PKKKSXIPDFGVKI-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- RUEJFLRIFUSIPM-UHFFFAOYSA-N N-(3-propan-2-ylphenyl)thiohydroxylamine Chemical compound C(C)(C)C=1C=C(NS)C=CC1 RUEJFLRIFUSIPM-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229940035676 analgesics Drugs 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 230000000507 anthelmentic effect Effects 0.000 description 1
- 229940124339 anthelmintic agent Drugs 0.000 description 1
- 239000000921 anthelmintic agent Substances 0.000 description 1
- 229940125715 antihistaminic agent Drugs 0.000 description 1
- 239000000739 antihistaminic agent Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 230000000147 hypnotic effect Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- KQGRMKLYONINOY-UHFFFAOYSA-N n-(3-methylphenyl)thiohydroxylamine Chemical compound CC1=CC=CC(NS)=C1 KQGRMKLYONINOY-UHFFFAOYSA-N 0.000 description 1
- 230000003533 narcotic effect Effects 0.000 description 1
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Substances [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- RZWQDAUIUBVCDD-UHFFFAOYSA-M sodium;benzenethiolate Chemical compound [Na+].[S-]C1=CC=CC=C1 RZWQDAUIUBVCDD-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000002048 spasmolytic effect Effects 0.000 description 1
- FWMUJAIKEJWSSY-UHFFFAOYSA-N sulfur dichloride Chemical compound ClSCl FWMUJAIKEJWSSY-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000004073 vulcanization Methods 0.000 description 1
- 239000008096 xylene Substances 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)
Priority Applications (20)
| 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 |
| CH5646256A CH364794A (de) | 1956-04-18 | 1956-04-18 | Verfahren zur Herstellung von neuen Mercapto-diphenylaminen |
| CH360059D CH360059A (de) | 1956-04-18 | 1956-04-19 | Verfahren zur Herstellung von neuen in 3-Stellung mit einer einwertigen Schwefelfunktion substituierten Phenothiazinen |
| ES0234296A ES234296A1 (es) | 1956-04-18 | 1957-03-18 | PROCEDIMIENTO PARA LA OBTENCIoN DE DERIVADOS FENOTIACiNICOS, SUSTITUiDOS EN POSICIoN 3 POR UNA FUNCION DE AZUFRE MONOVALENTE |
| DE1957S0052942 DE1128856B (de) | 1956-04-18 | 1957-03-29 | Verfahren zur Herstellung von in 3-Stellung durch schwefelhaltige Gruppen substituierten Phenthiazinderivaten |
| GB1738060A GB863550A (en) | 1956-04-18 | 1957-04-04 | 3-mercapto-phenthiazines |
| GB1105057A GB863547A (en) | 1956-04-18 | 1957-04-04 | 3-mercapto-phenthiazine |
| BE556725A BE556725A (OSRAM) | 1956-04-18 | 1957-04-16 | |
| US653058A US3239514A (en) | 1956-04-18 | 1957-04-16 | Phenothiazine derivatives substituted by a monovalent sulfur function in 3-position |
| NL216436A NL105268C (OSRAM) | 1956-04-18 | 1957-04-17 | |
| NL216435A NL105267C (OSRAM) | 1956-04-18 | 1957-04-17 | |
| FR1174268D FR1174268A (fr) | 1956-04-18 | 1957-04-17 | Nouveaux dérivés de la phénothiazine et leur préparation |
| BE565470A BE565470A (OSRAM) | 1956-04-18 | 1958-03-06 | |
| DE1958S0057244 DE1090667B (de) | 1956-04-18 | 1958-03-07 | Verfahren zur Herstellung von basischen Phenthiazinderivaten |
| CH5676458A CH374675A (de) | 1956-04-18 | 1958-03-07 | Verfahren zur Herstellung von neuen schwefelhaltigen Phenothiazin-Derivaten |
| NL225621A NL108580C (OSRAM) | 1956-04-18 | 1958-03-07 | |
| FR1203557D FR1203557A (fr) | 1956-04-18 | 1958-03-07 | Nouveaux dérivés basiques de la 3 alcoylmercapto phénothiazine substitués sur l'azote et leur préparation |
| GB748158A GB858140A (en) | 1956-04-18 | 1958-03-07 | The preparation of new basic phenothiazine derivatives |
| CY27564A CY275A (en) | 1956-04-18 | 1964-02-12 | The preparation of new basic phenothiazine derivatives |
| US420821A US3336197A (en) | 1956-04-18 | 1964-12-23 | Phenothiazine derivative |
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 |
|---|---|
| CH365379A true CH365379A (de) | 1962-11-15 |
Family
ID=25736343
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH3228356A CH365379A (de) | 1956-04-18 | 1956-04-18 | Verfahren zur Herstellung von neuen, in 3-Stellung mit einer einwertigen Schwefelfunktion substituierten Phenothiazinen |
| CH360059D CH360059A (de) | 1956-04-18 | 1956-04-19 | Verfahren zur Herstellung von neuen in 3-Stellung mit einer einwertigen Schwefelfunktion substituierten Phenothiazinen |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH360059D CH360059A (de) | 1956-04-18 | 1956-04-19 | Verfahren zur Herstellung von neuen in 3-Stellung mit einer einwertigen Schwefelfunktion substituierten Phenothiazinen |
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 |
Family Cites Families (5)
| 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. |
| 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 |
| BE552836A (OSRAM) | 1955-11-25 | |||
| 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
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 |
| GB858140A (en) | 1961-01-04 |
| DE1128856B (de) | 1962-05-03 |
| BE565470A (OSRAM) | 1958-09-06 |
| NL108580C (OSRAM) | 1964-06-15 |
| NL105268C (OSRAM) | 1963-07-15 |
| DE1090667B (de) | 1960-10-13 |
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