NO127970B - - Google Patents
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- Publication number
- NO127970B NO127970B NO02376/70A NO237670A NO127970B NO 127970 B NO127970 B NO 127970B NO 02376/70 A NO02376/70 A NO 02376/70A NO 237670 A NO237670 A NO 237670A NO 127970 B NO127970 B NO 127970B
- Authority
- NO
- Norway
- Prior art keywords
- isomer
- acid
- propylidene
- piperazinyl
- hydroxyethyl
- Prior art date
Links
- OSFBJERFMQCEQY-UHFFFAOYSA-N propylidene Chemical group [CH]CC OSFBJERFMQCEQY-UHFFFAOYSA-N 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- 150000001954 decanoic acid esters Chemical class 0.000 claims description 7
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical class CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 4
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 16
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 230000005764 inhibitory process Effects 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 229960002419 flupentixol Drugs 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- 239000000155 melt Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 4
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- NJMYODHXAKYRHW-DVZOWYKESA-N cis-flupenthixol Chemical compound C1CN(CCO)CCN1CC\C=C\1C2=CC(C(F)(F)F)=CC=C2SC2=CC=CC=C2/1 NJMYODHXAKYRHW-DVZOWYKESA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 150000003840 hydrochlorides Chemical class 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 230000000701 neuroleptic effect Effects 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 235000006408 oxalic acid Nutrition 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 208000024891 symptom Diseases 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 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 description 1
- QWBFJJKUZDTEJV-UHFFFAOYSA-N 2-(trifluoromethyl)-2H-thiopyrano[3,2-b]chromen-10-one Chemical compound FC(C1SC=2C(C3=CC=CC=C3OC2C=C1)=O)(F)F QWBFJJKUZDTEJV-UHFFFAOYSA-N 0.000 description 1
- WFCSWCVEJLETKA-UHFFFAOYSA-N 2-piperazin-1-ylethanol Chemical compound OCCN1CCNCC1 WFCSWCVEJLETKA-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
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 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
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 206010039897 Sedation Diseases 0.000 description 1
- 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 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- VMWNQDUVQKEIOC-CYBMUJFWSA-N apomorphine Chemical compound C([C@H]1N(C)CC2)C3=CC=C(O)C(O)=C3C3=C1C2=CC=C3 VMWNQDUVQKEIOC-CYBMUJFWSA-N 0.000 description 1
- 229960004046 apomorphine Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000003405 delayed action preparation Substances 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 230000035929 gnawing Effects 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- DQEUYIQDSMINEY-UHFFFAOYSA-M magnesium;prop-1-ene;bromide Chemical compound [Mg+2].[Br-].[CH2-]C=C DQEUYIQDSMINEY-UHFFFAOYSA-M 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 239000003176 neuroleptic agent Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- -1 propylidene 2-trifluoromethyl-thiaxanthene Chemical compound 0.000 description 1
- 238000001671 psychotherapy Methods 0.000 description 1
- 230000000698 schizophrenic effect Effects 0.000 description 1
- 230000036280 sedation Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US83525069A | 1969-06-20 | 1969-06-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO127970B true NO127970B (de) | 1973-09-10 |
Family
ID=25269034
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO02376/70A NO127970B (de) | 1969-06-20 | 1970-06-18 |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US3681346A (de) |
| AT (1) | AT294088B (de) |
| BE (1) | BE752286A (de) |
| CH (1) | CH534180A (de) |
| DK (1) | DK128743B (de) |
| FI (1) | FI51194C (de) |
| FR (1) | FR2052997B1 (de) |
| GB (1) | GB1275181A (de) |
| IE (1) | IE34684B1 (de) |
| NL (1) | NL7009000A (de) |
| NO (1) | NO127970B (de) |
| SE (1) | SE384025B (de) |
| ZA (1) | ZA703914B (de) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4035503A (en) * | 1973-11-30 | 1977-07-12 | Kefalas A/S | Xanthene and thioxanthene derivatives, compositions thereof and a method of preparation thereof |
| US4022896A (en) * | 1973-11-30 | 1977-05-10 | Kefalas A/S | Xanthene and thioxanthene compositions and method of treating |
| GB1480593A (en) * | 1973-11-30 | 1977-07-20 | Kefalas As | Xanthene and thioxanthene derivatives having pharmaceutical activity |
| US4107430A (en) * | 1976-10-20 | 1978-08-15 | Pfizer Inc. | Conversion of trans- to cis-N,N-dimethyl-9-[3-(4-methyl-1-piperazinyl)propylidene]-thioxanthene-2-sulfonamide and recovery of the cis-isomer |
| US4232021A (en) * | 1979-01-25 | 1980-11-04 | Kefalas A/S | Anti-depressant methods |
| GB8628903D0 (en) * | 1986-12-03 | 1987-01-07 | Lunbeck A S H | Neuroleptic compounds |
| ITMI20032024A1 (it) * | 2003-10-17 | 2005-04-18 | Laboratorio Chimico Int Spa | Procedimento per la preparazione dello z-flupentixol |
| CN102002034B (zh) * | 2009-08-28 | 2012-11-28 | 江苏恩华药业股份有限公司 | 盐酸氟哌噻吨异构体的分离方法 |
| CN103804347B (zh) * | 2012-11-09 | 2017-10-03 | H.隆德贝克有限公司 | 制备含有氟哌噻吨的药物组合物的方法 |
| CN104177330A (zh) * | 2014-09-10 | 2014-12-03 | 宁辉 | 盐酸氟哌噻吨结晶化合物及其药物组合物 |
| 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 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE585338A (de) * | 1958-12-04 | |||
| CH410002A (de) * | 1959-06-30 | 1966-03-31 | Hoffmann La Roche | Verfahren zur cis-/trans-Isomerisierung von tricyclischen Verbindungen |
| US3282930A (en) * | 1962-08-17 | 1966-11-01 | Smith Kline French Lab | Hydroxyalkylenepiperazine derivatives and analogs thereof |
| US3350268A (en) * | 1965-07-01 | 1967-10-31 | Squibb & Sons Inc | Compositions and method of employing phenothiazine salts |
-
1969
- 1969-06-20 US US835250A patent/US3681346A/en not_active Expired - Lifetime
-
1970
- 1970-06-09 ZA ZA703914A patent/ZA703914B/xx unknown
- 1970-06-15 AT AT535470A patent/AT294088B/de active
- 1970-06-15 IE IE772/70A patent/IE34684B1/xx unknown
- 1970-06-16 SE SE7008314A patent/SE384025B/xx unknown
- 1970-06-18 CH CH927070A patent/CH534180A/de not_active IP Right Cessation
- 1970-06-18 FI FI701721A patent/FI51194C/fi active
- 1970-06-18 NO NO02376/70A patent/NO127970B/no unknown
- 1970-06-19 NL NL7009000A patent/NL7009000A/xx unknown
- 1970-06-19 BE BE752286D patent/BE752286A/xx not_active IP Right Cessation
- 1970-06-19 FR FR7022760A patent/FR2052997B1/fr not_active Expired
- 1970-06-19 DK DK316670AA patent/DK128743B/da not_active IP Right Cessation
- 1970-06-22 GB GB30254/70A patent/GB1275181A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB1275181A (en) | 1972-05-24 |
| DE2029084B2 (de) | 1976-09-23 |
| US3681346A (en) | 1972-08-01 |
| IE34684B1 (en) | 1975-07-23 |
| DE2029084A1 (de) | 1971-01-07 |
| FR2052997A1 (de) | 1971-04-16 |
| AT294088B (de) | 1971-11-10 |
| ZA703914B (en) | 1971-02-24 |
| FR2052997B1 (de) | 1974-08-30 |
| FI51194C (fi) | 1976-11-10 |
| NL7009000A (de) | 1970-12-22 |
| SE384025B (sv) | 1976-04-12 |
| IE34684L (en) | 1970-12-20 |
| DK128743B (da) | 1974-06-24 |
| BE752286A (fr) | 1970-12-01 |
| CH534180A (de) | 1973-02-28 |
| FI51194B (de) | 1976-08-02 |
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