PL90396B1 - - Google Patents
Download PDFInfo
- Publication number
- PL90396B1 PL90396B1 PL16491173A PL16491173A PL90396B1 PL 90396 B1 PL90396 B1 PL 90396B1 PL 16491173 A PL16491173 A PL 16491173A PL 16491173 A PL16491173 A PL 16491173A PL 90396 B1 PL90396 B1 PL 90396B1
- Authority
- PL
- Poland
- Prior art keywords
- thia
- anion
- isochroman
- general formula
- dioxo
- Prior art date
Links
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- -1 tosyl anion Chemical class 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
- 150000008051 alkyl sulfates Chemical class 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 150000001450 anions Chemical class 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 2
- 230000002152 alkylating effect Effects 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
- 239000011630 iodine Substances 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- CTYRPMDGLDAWRQ-UHFFFAOYSA-N phenyl hydrogen sulfate Chemical compound OS(=O)(=O)OC1=CC=CC=C1 CTYRPMDGLDAWRQ-UHFFFAOYSA-N 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 238000005956 quaternization reaction Methods 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 125000005526 alkyl sulfate group Chemical group 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 239000000203 mixture Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 208000009132 Catalepsy Diseases 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 206010021118 Hypotonia Diseases 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 206010047853 Waxy flexibility Diseases 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
- 230000036640 muscle relaxation Effects 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- QLAJNZSPVITUCQ-UHFFFAOYSA-N 1,3,2-dioxathietane 2,2-dioxide Chemical compound O=S1(=O)OCO1 QLAJNZSPVITUCQ-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 230000003556 anti-epileptic effect Effects 0.000 description 1
- 239000001961 anticonvulsive agent Substances 0.000 description 1
- 229960003965 antiepileptics Drugs 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000002903 catalepsic effect Effects 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- VRZVPALEJCLXPR-UHFFFAOYSA-N ethyl 4-methylbenzenesulfonate Chemical compound CCOS(=O)(=O)C1=CC=C(C)C=C1 VRZVPALEJCLXPR-UHFFFAOYSA-N 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- FNYZNEUGGYUYEX-UHFFFAOYSA-N iodomethane;hydrate Chemical compound O.IC FNYZNEUGGYUYEX-UHFFFAOYSA-N 0.000 description 1
- HEBMCVBCEDMUOF-UHFFFAOYSA-N isochromane Chemical compound C1=CC=C2COCCC2=C1 HEBMCVBCEDMUOF-UHFFFAOYSA-N 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 239000003158 myorelaxant agent Substances 0.000 description 1
- FWFGVMYFCODZRD-UHFFFAOYSA-N oxidanium;hydrogen sulfate Chemical compound O.OS(O)(=O)=O FWFGVMYFCODZRD-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 208000020016 psychiatric disease Diseases 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
- C07D327/02—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms one oxygen atom and one sulfur atom
- C07D327/06—Six-membered rings
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)
- Thiazole And Isothizaole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DD16536472A DD103243A1 (en, 2012) | 1972-08-30 | 1972-08-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL90396B1 true PL90396B1 (en, 2012) | 1977-01-31 |
Family
ID=5488020
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL16491173A PL90396B1 (en, 2012) | 1972-08-30 | 1973-08-29 |
Country Status (16)
| Country | Link |
|---|---|
| JP (1) | JPS5040714A (en, 2012) |
| AT (1) | AT324346B (en, 2012) |
| BE (1) | BE804111A (en, 2012) |
| CH (1) | CH581128A5 (en, 2012) |
| CS (1) | CS190618B1 (en, 2012) |
| DD (1) | DD103243A1 (en, 2012) |
| DK (1) | DK132431C (en, 2012) |
| FI (1) | FI52724C (en, 2012) |
| FR (1) | FR2197596B1 (en, 2012) |
| GB (1) | GB1383459A (en, 2012) |
| HU (1) | HU165645B (en, 2012) |
| NL (1) | NL7311752A (en, 2012) |
| PL (1) | PL90396B1 (en, 2012) |
| RO (1) | RO63883A2 (en, 2012) |
| SE (1) | SE382814B (en, 2012) |
| SU (1) | SU512207A1 (en, 2012) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4924075B1 (en, 2012) * | 1969-12-22 | 1974-06-20 |
-
1972
- 1972-08-30 DD DD16536472A patent/DD103243A1/xx unknown
-
1973
- 1973-08-07 AT AT691273A patent/AT324346B/de not_active IP Right Cessation
- 1973-08-20 RO RO75844A patent/RO63883A2/ro unknown
- 1973-08-20 CH CH1194673A patent/CH581128A5/xx not_active IP Right Cessation
- 1973-08-23 CS CS590873A patent/CS190618B1/cs unknown
- 1973-08-27 NL NL7311752A patent/NL7311752A/xx not_active Application Discontinuation
- 1973-08-28 BE BE135017A patent/BE804111A/xx unknown
- 1973-08-28 SE SE7311691A patent/SE382814B/xx unknown
- 1973-08-29 GB GB4068073A patent/GB1383459A/en not_active Expired
- 1973-08-29 DK DK473673A patent/DK132431C/da active
- 1973-08-29 PL PL16491173A patent/PL90396B1/pl unknown
- 1973-08-29 SU SU1955350A patent/SU512207A1/ru active
- 1973-08-29 FI FI268373A patent/FI52724C/fi active
- 1973-08-30 JP JP9779373A patent/JPS5040714A/ja active Pending
- 1973-08-30 FR FR7331470A patent/FR2197596B1/fr not_active Expired
- 1973-08-30 HU HUAE000391 patent/HU165645B/hu unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB1383459A (en) | 1974-02-12 |
| DK132431B (da) | 1975-12-08 |
| FR2197596A1 (en, 2012) | 1974-03-29 |
| DD103243A1 (en, 2012) | 1974-01-12 |
| FI52724C (fi) | 1977-11-10 |
| CS190618B1 (en) | 1979-06-29 |
| CH581128A5 (en, 2012) | 1976-10-29 |
| SE382814B (sv) | 1976-02-16 |
| HU165645B (en, 2012) | 1974-10-28 |
| FI52724B (en, 2012) | 1977-08-01 |
| BE804111A (fr) | 1974-02-28 |
| DK132431C (da) | 1976-05-10 |
| SU512207A1 (ru) | 1976-04-30 |
| NL7311752A (en, 2012) | 1974-03-04 |
| FR2197596B1 (en, 2012) | 1977-01-28 |
| AT324346B (de) | 1975-08-25 |
| RO63883A2 (ro) | 1978-09-15 |
| JPS5040714A (en, 2012) | 1975-04-14 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE68908374T2 (de) | Propenonoximether, Verfahren zu dessen Herstellung sowie diese enthaltende Arzneinmittel. | |
| CH630912A5 (de) | Verfahren zur herstellung von 1,2-dihydronaphthalinderivaten. | |
| EP0000220B1 (de) | Dihydrouracile, Verfahren zu ihrer Herstellung und sie enthaltende Arzneimittel | |
| PL91729B1 (en, 2012) | ||
| WO1994007862A1 (de) | Neue asymmetrisch substituierte bis-naphthalimide | |
| DE2426149B2 (de) | 7-Fluor-substituierte Phenothiazine, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Mittel | |
| Zinnes et al. | 1, 2-Benzothiazines. 6. 3-Carbamoyl-4-hydroxy-2H-1, 2-benzothiazine 1, 1-dioxides as antiinflammatory agents | |
| GB1567313A (en) | 2,3-dihydro-3-hydroxy-1h-benz-(de)isoquinolin-1-one derivatives | |
| US3320247A (en) | Phenthiazine compounds | |
| PL90396B1 (en, 2012) | ||
| CH619683A5 (en, 2012) | ||
| EP0472166A1 (de) | Tricyclische Pyridonderivate | |
| US3536725A (en) | Cyanoethylated derivatives of 2,3,4,6,7,12-hexahydroindolo(2,3-alpha)-quinolizine | |
| US3417094A (en) | Optically active 1,2,3,4,5,6-hexahydro-6-phenyl - 2,6 - methano - 3 - benzazocines an | |
| US4259494A (en) | Tricyclic sulphoximides | |
| EP0138137A1 (de) | 4-Thioxo-benzopyrano(2,3-d)pyrimidin-derivate sowie Verfahren zu deren Herstellung | |
| US3828073A (en) | 4-hydroxy-2h-1-benzothiopyran-3-carboxamides and their corresponding s-oxides | |
| US3328406A (en) | Amide and piperazides of carbazole-9-glyoxylic acid | |
| PL163988B1 (pl) | Sposób wytwarzania nowych stereoizomerów 4-/3-{N- etylo-N-[3-/propylosulfinylo/ propylo]amino}-2 hydroksypropoksy/benzonitrylu PL PL | |
| US3625948A (en) | Process for the preparation of hexahydromethanobenzazocines | |
| US3018286A (en) | Methoxy-z-j | |
| DE927330C (de) | Verfahren zur Herstellung neuer Dioxopiperidine | |
| US3749715A (en) | Method of preparing 2,3-dihydro-1h-pyrido-(2,3-b)(1,4)-thiazin-2-ones | |
| US3644417A (en) | Coronary vasodilator compounds | |
| DE2438965A1 (de) | Basisch substituierte 3,4-dihydro2h-isochinolin-1-thione und verfahren zu ihrer herstellung |