DE2609574C3 - 1 -^-Fluor-S-trifluormethylthiophenyD-piperazin, dessen Salze, Verfahren zu dessen Herstellung und Arzneimittel - Google Patents
1 -^-Fluor-S-trifluormethylthiophenyD-piperazin, dessen Salze, Verfahren zu dessen Herstellung und ArzneimittelInfo
- Publication number
- DE2609574C3 DE2609574C3 DE2609574A DE2609574A DE2609574C3 DE 2609574 C3 DE2609574 C3 DE 2609574C3 DE 2609574 A DE2609574 A DE 2609574A DE 2609574 A DE2609574 A DE 2609574A DE 2609574 C3 DE2609574 C3 DE 2609574C3
- Authority
- DE
- Germany
- Prior art keywords
- trifluoromethylthio
- fluoro
- compound
- piperazine
- salts
- 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
- 150000003839 salts Chemical class 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 11
- 239000000203 mixture Substances 0.000 description 11
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
- 239000002904 solvent Substances 0.000 description 7
- OMDVCPVYJUCGHK-UHFFFAOYSA-N 4-fluoro-3-(trifluoromethylsulfanyl)aniline Chemical compound NC1=CC=C(F)C(SC(F)(F)F)=C1 OMDVCPVYJUCGHK-UHFFFAOYSA-N 0.000 description 6
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- 239000002830 appetite depressant Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 229910052938 sodium sulfate Inorganic materials 0.000 description 6
- 235000011152 sodium sulphate Nutrition 0.000 description 6
- 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 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 229960001413 acetanilide Drugs 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- -1 hydrobromic acid Forms compound Chemical class 0.000 description 4
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- TVJNFBMZRGVEOO-UHFFFAOYSA-N 1-bromo-4-nitro-2-(trifluoromethylsulfanyl)benzene Chemical compound [O-][N+](=O)C1=CC=C(Br)C(SC(F)(F)F)=C1 TVJNFBMZRGVEOO-UHFFFAOYSA-N 0.000 description 3
- QTBPZZLJAGVEAM-UHFFFAOYSA-N 4-bromo-3-(trifluoromethylsulfanyl)aniline Chemical compound NC1=CC=C(Br)C(SC(F)(F)F)=C1 QTBPZZLJAGVEAM-UHFFFAOYSA-N 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical group Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 150000002828 nitro derivatives Chemical class 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- DBGIVFWFUFKIQN-UHFFFAOYSA-N (+-)-Fenfluramine Chemical compound CCNC(C)CC1=CC=CC(C(F)(F)F)=C1 DBGIVFWFUFKIQN-UHFFFAOYSA-N 0.000 description 2
- WXKUQZCCHVFRGZ-UHFFFAOYSA-N 1-[4-fluoro-3-(trifluoromethylsulfanyl)phenyl]piperazine Chemical compound C1=C(SC(F)(F)F)C(F)=CC=C1N1CCNCC1 WXKUQZCCHVFRGZ-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 239000012876 carrier material Substances 0.000 description 2
- 239000012259 ether extract Substances 0.000 description 2
- 229960001582 fenfluramine Drugs 0.000 description 2
- 230000037406 food intake Effects 0.000 description 2
- 235000012631 food intake Nutrition 0.000 description 2
- 238000001640 fractional crystallisation Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 235000003270 potassium fluoride Nutrition 0.000 description 2
- 239000011698 potassium fluoride Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 235000011150 stannous chloride Nutrition 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 2
- GRMGTJHSIVCGEW-UHFFFAOYSA-N 1-[4-fluoro-3-(trifluoromethyl)phenyl]piperazine Chemical compound C1=C(C(F)(F)F)C(F)=CC=C1N1CCNCC1 GRMGTJHSIVCGEW-UHFFFAOYSA-N 0.000 description 1
- CAKWJBKQZUOMMF-UHFFFAOYSA-N 1-fluoro-4-nitro-2-(trifluoromethylsulfanyl)benzene Chemical compound [O-][N+](=O)C1=CC=C(F)C(SC(F)(F)F)=C1 CAKWJBKQZUOMMF-UHFFFAOYSA-N 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
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 208000008589 Obesity Diseases 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000003575 carbonaceous material Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 235000021316 daily nutritional intake Nutrition 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 231100000518 lethal Toxicity 0.000 description 1
- 230000001665 lethal effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 231100001224 moderate toxicity Toxicity 0.000 description 1
- 230000004899 motility Effects 0.000 description 1
- 230000037023 motor activity Effects 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 235000020824 obesity Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 150000004885 piperazines Chemical class 0.000 description 1
- 239000013558 reference substance Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/096—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7507650A FR2303549A1 (fr) | 1975-03-12 | 1975-03-12 | Nouveau derive monosubstitue de piperazine, ses sels, sa preparation et les medicaments qui en renferment |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2609574A1 DE2609574A1 (de) | 1976-09-23 |
| DE2609574B2 DE2609574B2 (de) | 1977-10-27 |
| DE2609574C3 true DE2609574C3 (de) | 1978-06-22 |
Family
ID=9152445
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2609574A Expired DE2609574C3 (de) | 1975-03-12 | 1976-03-08 | 1 -^-Fluor-S-trifluormethylthiophenyD-piperazin, dessen Salze, Verfahren zu dessen Herstellung und Arzneimittel |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US4044132A (enExample) |
| JP (1) | JPS51118779A (enExample) |
| AT (1) | AT350575B (enExample) |
| AU (1) | AU497004B2 (enExample) |
| BE (1) | BE839516A (enExample) |
| CA (1) | CA1058180A (enExample) |
| CH (1) | CH608796A5 (enExample) |
| DE (1) | DE2609574C3 (enExample) |
| DK (1) | DK139266B (enExample) |
| ES (1) | ES445969A1 (enExample) |
| FR (1) | FR2303549A1 (enExample) |
| GB (1) | GB1503626A (enExample) |
| GR (1) | GR59892B (enExample) |
| IE (1) | IE42710B1 (enExample) |
| LU (1) | LU74548A1 (enExample) |
| NL (1) | NL7602538A (enExample) |
| NO (1) | NO760837L (enExample) |
| SE (1) | SE7602760L (enExample) |
| ZA (1) | ZA761393B (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4202898A (en) * | 1978-06-05 | 1980-05-13 | Synthelabo | Method of treating anxiety and depression |
| EP0259264A1 (de) * | 1986-09-03 | 1988-03-09 | Ciba-Geigy Ag | Neue 4-Methylphthalimide |
| ATE67186T1 (de) * | 1986-09-03 | 1991-09-15 | Ciba Geigy Ag | 3-methylphthalimide. |
| DE3737985A1 (de) * | 1987-11-09 | 1989-05-18 | Bayer Ag | Am aromatischen kern fluor enthaltende fluormethoxy- und fluormethylthio-aminobenzole und deren herstellung |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3637705A (en) * | 1968-10-01 | 1972-01-25 | Abbott Lab | N-3 4-dihalo phenyl piperazines |
| FR2179491B1 (enExample) * | 1972-04-10 | 1975-10-10 | Synthelabo |
-
1975
- 1975-03-12 FR FR7507650A patent/FR2303549A1/fr active Granted
-
1976
- 1976-02-27 SE SE7602760A patent/SE7602760L/xx not_active Application Discontinuation
- 1976-03-05 IE IE464/76A patent/IE42710B1/en unknown
- 1976-03-08 DE DE2609574A patent/DE2609574C3/de not_active Expired
- 1976-03-08 ZA ZA761393A patent/ZA761393B/xx unknown
- 1976-03-09 CA CA247,419A patent/CA1058180A/en not_active Expired
- 1976-03-10 NO NO760837A patent/NO760837L/no unknown
- 1976-03-10 GB GB9617/76A patent/GB1503626A/en not_active Expired
- 1976-03-11 DK DK106076AA patent/DK139266B/da unknown
- 1976-03-11 ES ES445969A patent/ES445969A1/es not_active Expired
- 1976-03-11 US US05/665,884 patent/US4044132A/en not_active Expired - Lifetime
- 1976-03-11 NL NL7602538A patent/NL7602538A/xx not_active Application Discontinuation
- 1976-03-12 BE BE165121A patent/BE839516A/xx unknown
- 1976-03-12 AU AU11971/76A patent/AU497004B2/en not_active Expired
- 1976-03-12 LU LU74548A patent/LU74548A1/xx unknown
- 1976-03-12 AT AT183476A patent/AT350575B/de not_active IP Right Cessation
- 1976-03-12 CH CH763135A patent/CH608796A5/xx not_active IP Right Cessation
- 1976-03-12 JP JP51027623A patent/JPS51118779A/ja active Pending
- 1976-03-12 GR GR50289A patent/GR59892B/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPS51118779A (en) | 1976-10-18 |
| DK139266B (da) | 1979-01-22 |
| BE839516A (fr) | 1976-09-13 |
| LU74548A1 (enExample) | 1976-09-01 |
| FR2303549B1 (enExample) | 1979-08-10 |
| DE2609574A1 (de) | 1976-09-23 |
| DK139266C (enExample) | 1979-06-25 |
| ZA761393B (en) | 1977-02-23 |
| AU497004B2 (en) | 1978-11-16 |
| SE7602760L (sv) | 1976-09-13 |
| ES445969A1 (es) | 1977-05-16 |
| ATA183476A (de) | 1978-11-15 |
| AT350575B (de) | 1979-06-11 |
| GB1503626A (en) | 1978-03-15 |
| US4044132A (en) | 1977-08-23 |
| IE42710B1 (en) | 1980-10-08 |
| FR2303549A1 (fr) | 1976-10-08 |
| CA1058180A (en) | 1979-07-10 |
| AU1197176A (en) | 1977-09-15 |
| CH608796A5 (enExample) | 1979-01-31 |
| GR59892B (en) | 1978-03-15 |
| NO760837L (enExample) | 1976-09-14 |
| DE2609574B2 (de) | 1977-10-27 |
| DK106076A (enExample) | 1976-09-13 |
| IE42710L (en) | 1976-09-12 |
| NL7602538A (nl) | 1976-09-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| EHJ | Ceased/non-payment of the annual fee |