FR2368485A1 - Procede de transformation du trans-n,n-dimethyl- 9 -(3-(4-methyl-1-piperazinyl) propylidene) thioxanthene-2-sulfamide en son isomere cis et de separation de cet isomere - Google Patents
Procede de transformation du trans-n,n-dimethyl- 9 -(3-(4-methyl-1-piperazinyl) propylidene) thioxanthene-2-sulfamide en son isomere cis et de separation de cet isomereInfo
- Publication number
- FR2368485A1 FR2368485A1 FR7731487A FR7731487A FR2368485A1 FR 2368485 A1 FR2368485 A1 FR 2368485A1 FR 7731487 A FR7731487 A FR 7731487A FR 7731487 A FR7731487 A FR 7731487A FR 2368485 A1 FR2368485 A1 FR 2368485A1
- Authority
- FR
- France
- Prior art keywords
- isomer
- cis isomer
- trans
- piperazinyl
- dimethyl
- 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.)
- Granted
Links
- -1 3- (4-METHYL-1-PIPERAZINYL) PROPYLIDENE Chemical class 0.000 title abstract 3
- 238000000034 method Methods 0.000 title 1
- 238000000926 separation method Methods 0.000 title 1
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 abstract 3
- 239000002904 solvent Substances 0.000 abstract 2
- 229940124530 sulfonamide Drugs 0.000 abstract 2
- 238000002512 chemotherapy Methods 0.000 abstract 1
- 238000002955 isolation Methods 0.000 abstract 1
- 238000006317 isomerization reaction Methods 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 239000003495 polar organic solvent Substances 0.000 abstract 1
- 230000001737 promoting effect Effects 0.000 abstract 1
- 208000020016 psychiatric disease Diseases 0.000 abstract 1
- 239000006228 supernatant Substances 0.000 abstract 1
- 230000009466 transformation Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
- C07D335/04—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D335/10—Dibenzothiopyrans; Hydrogenated dibenzothiopyrans
- C07D335/12—Thioxanthenes
- C07D335/20—Thioxanthenes with hydrocarbon radicals, substituted by amino radicals, directly attached in position 9
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Neurology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cephalosporin Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
L'invention concerne la transformation de l'isomère trans en l'isomère cis du N,N-diméthyl-9-Ø3-(4-méthyl-1-pipérazinyl)propylidèneõthioxanthène-2-sulfamide et l'isolement de l'isomère cis. L'isomère trans est isomérisé en l'isomère cis par contact avec une base forte dans un solvant organique polaire. En utilisant un solvant organique dans lequel la solubilité de l'isomère cis est sensiblement plus faible que celle de l'isomère trans, on peut précipiter sélectivement l'isomère cis dans ce solvant, en favorisant ainsi une isomérisation additionnelle en l'isomère cis dans la liqueur surnageante, l'isomère cis étant ensuite séparé. Le N'N-diméthyl-9-Ø3-(4-méthyl-l-pipérazinyl)-propylidèneõthioxanthène-2-sulfamide, notamment l'isomère cis, offre un grand intérêt dans la chimiothérapie de certaines maladies mentales.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US05/734,081 US4107430A (en) | 1976-10-20 | 1976-10-20 | Conversion of trans- to cis-N,N-dimethyl-9-[3-(4-methyl-1-piperazinyl)propylidene]-thioxanthene-2-sulfonamide and recovery of the cis-isomer |
Publications (2)
Publication Number | Publication Date |
---|---|
FR2368485A1 true FR2368485A1 (fr) | 1978-05-19 |
FR2368485B1 FR2368485B1 (fr) | 1983-01-07 |
Family
ID=24950235
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
FR7731487A Granted FR2368485A1 (fr) | 1976-10-20 | 1977-10-19 | Procede de transformation du trans-n,n-dimethyl- 9 -(3-(4-methyl-1-piperazinyl) propylidene) thioxanthene-2-sulfamide en son isomere cis et de separation de cet isomere |
Country Status (37)
Country | Link |
---|---|
US (1) | US4107430A (fr) |
JP (1) | JPS5353674A (fr) |
AR (1) | AR213867A1 (fr) |
AT (1) | AT360025B (fr) |
AU (1) | AU499048B2 (fr) |
BE (1) | BE859907A (fr) |
BG (1) | BG32852A3 (fr) |
CA (1) | CA1085399A (fr) |
CH (1) | CH625519A5 (fr) |
CS (1) | CS192494B2 (fr) |
DD (1) | DD133438A5 (fr) |
DE (1) | DE2746762C3 (fr) |
DK (1) | DK159314C (fr) |
ES (1) | ES463343A1 (fr) |
FI (1) | FI63939C (fr) |
FR (1) | FR2368485A1 (fr) |
GB (1) | GB1542004A (fr) |
GR (1) | GR69786B (fr) |
HK (1) | HK31081A (fr) |
HU (1) | HU173644B (fr) |
IE (1) | IE45715B1 (fr) |
IL (1) | IL53056A (fr) |
IN (1) | IN146954B (fr) |
LU (1) | LU78336A1 (fr) |
MX (1) | MX4843E (fr) |
MY (1) | MY8100275A (fr) |
NL (1) | NL172062C (fr) |
NO (1) | NO148713C (fr) |
NZ (1) | NZ185461A (fr) |
PH (1) | PH13941A (fr) |
PL (1) | PL106962B1 (fr) |
PT (1) | PT67171B (fr) |
RO (1) | RO74135A (fr) |
SE (1) | SE437828B (fr) |
SU (1) | SU831078A3 (fr) |
YU (1) | YU40978B (fr) |
ZA (1) | ZA776216B (fr) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2998303B1 (fr) | 2014-09-17 | 2018-06-13 | B & G Partners, LLC | Derivées de phenothiazine et procédés pour traiter des tumeurs |
CN107987053B (zh) * | 2017-12-08 | 2023-04-14 | 植恩生物技术股份有限公司 | 一种高纯度z型盐酸氟哌噻吨的制备方法 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB881488A (en) * | 1959-06-19 | 1961-11-01 | Hoffmann La Roche | Isomerisation process |
SU540867A1 (ru) * | 1975-06-16 | 1976-12-30 | Предприятие П/Я М-5927 | Способ получени цис- -диметил9-/3-(4-метил-1-пиперазинил)-пропилиден/-тиоксантен-2-сульфонамида |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3115502A (en) * | 1959-06-19 | 1963-12-24 | Hoffmann La Roche | Method of isomerizing basically substituted stereoisomeric thioxanthenes |
US3310553A (en) * | 1962-09-25 | 1967-03-21 | Pfizer & Co C | Alkylated thioxathenesulfonamides |
US3514449A (en) * | 1967-01-16 | 1970-05-26 | Pfizer & Co C | Process for separating the cis isomer from a mixture of cis and trans n-(3 - (2 - chlorodibenz(b,e)oxepin - 11(6h)-ylidene)-propyl)piperazine |
US3681346A (en) * | 1969-06-20 | 1972-08-01 | Kefalas As | {60 -isomer of the decanoic acid ester of 10-{8 3,-(4-hydroxyethyl-1-piperazinyl)propylidene{9 -2-trifluoro-methyl thiaxanthene, acid addition salts thereof, method of use and compositions |
-
1976
- 1976-10-20 US US05/734,081 patent/US4107430A/en not_active Expired - Lifetime
-
1977
- 1977-04-19 AU AU29690/77A patent/AU499048B2/en not_active Expired
- 1977-09-26 SE SE7710759A patent/SE437828B/sv not_active IP Right Cessation
- 1977-10-03 IN IN286/DEL/77A patent/IN146954B/en unknown
- 1977-10-04 GR GR54504A patent/GR69786B/el unknown
- 1977-10-05 IL IL53056A patent/IL53056A/xx unknown
- 1977-10-07 PH PH20316A patent/PH13941A/en unknown
- 1977-10-10 YU YU2438/77A patent/YU40978B/xx unknown
- 1977-10-13 AT AT732077A patent/AT360025B/de not_active IP Right Cessation
- 1977-10-14 MX MX776482U patent/MX4843E/es unknown
- 1977-10-17 FI FI773073A patent/FI63939C/fi not_active IP Right Cessation
- 1977-10-17 JP JP12437277A patent/JPS5353674A/ja active Granted
- 1977-10-17 RO RO7791862A patent/RO74135A/fr unknown
- 1977-10-18 DE DE2746762A patent/DE2746762C3/de not_active Expired
- 1977-10-18 BG BG7737599A patent/BG32852A3/xx unknown
- 1977-10-18 CA CA288,928A patent/CA1085399A/fr not_active Expired
- 1977-10-18 CH CH1271377A patent/CH625519A5/fr not_active IP Right Cessation
- 1977-10-18 PL PL1977201585A patent/PL106962B1/pl unknown
- 1977-10-18 PT PT67171A patent/PT67171B/pt unknown
- 1977-10-18 LU LU78336A patent/LU78336A1/fr unknown
- 1977-10-18 NZ NZ185461A patent/NZ185461A/xx unknown
- 1977-10-19 ZA ZA00776216A patent/ZA776216B/xx unknown
- 1977-10-19 CS CS776800A patent/CS192494B2/cs unknown
- 1977-10-19 ES ES463343A patent/ES463343A1/es not_active Expired
- 1977-10-19 GB GB7743542A patent/GB1542004A/en not_active Expired
- 1977-10-19 NO NO773588A patent/NO148713C/no unknown
- 1977-10-19 SU SU772531950A patent/SU831078A3/ru active
- 1977-10-19 BE BE181889A patent/BE859907A/fr not_active IP Right Cessation
- 1977-10-19 IE IE2134/77A patent/IE45715B1/en not_active IP Right Cessation
- 1977-10-19 NL NLAANVRAGE7711471,A patent/NL172062C/xx not_active IP Right Cessation
- 1977-10-19 HU HU77PI595A patent/HU173644B/hu unknown
- 1977-10-19 DK DK465377A patent/DK159314C/da not_active IP Right Cessation
- 1977-10-19 FR FR7731487A patent/FR2368485A1/fr active Granted
- 1977-10-20 AR AR269655A patent/AR213867A1/es active
- 1977-10-20 DD DD77201628A patent/DD133438A5/xx unknown
-
1981
- 1981-07-02 HK HK310/81A patent/HK31081A/xx not_active IP Right Cessation
- 1981-12-30 MY MY275/81A patent/MY8100275A/xx unknown
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB881488A (en) * | 1959-06-19 | 1961-11-01 | Hoffmann La Roche | Isomerisation process |
SU540867A1 (ru) * | 1975-06-16 | 1976-12-30 | Предприятие П/Я М-5927 | Способ получени цис- -диметил9-/3-(4-метил-1-пиперазинил)-пропилиден/-тиоксантен-2-сульфонамида |
Non-Patent Citations (1)
Title |
---|
CA1977 * |
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