DE1212537B - Verfahren zur Herstellung basischer Phenoxazinderivate und ihrer Salze - Google Patents
Verfahren zur Herstellung basischer Phenoxazinderivate und ihrer SalzeInfo
- Publication number
- DE1212537B DE1212537B DEB66847A DEB0066847A DE1212537B DE 1212537 B DE1212537 B DE 1212537B DE B66847 A DEB66847 A DE B66847A DE B0066847 A DEB0066847 A DE B0066847A DE 1212537 B DE1212537 B DE 1212537B
- Authority
- DE
- Germany
- Prior art keywords
- phenoxazine
- general formula
- hydroxyethyl
- derivative
- piperidine
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 10
- 150000003839 salts Chemical class 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title claims description 4
- 125000001644 phenoxazinyl group Chemical class C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 title claims 4
- -1 3 - butyryl -10 - (3 - chloropropyl) - phenoxazine Chemical compound 0.000 claims description 16
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 claims description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 9
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 5
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 4
- LDSQQXKSEFZAPE-UHFFFAOYSA-N 2-piperidin-4-ylethanol Chemical compound OCCC1CCNCC1 LDSQQXKSEFZAPE-UHFFFAOYSA-N 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 150000003053 piperidines Chemical class 0.000 claims description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 4
- 235000009518 sodium iodide Nutrition 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 238000001953 recrystallisation Methods 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 150000002991 phenoxazines Chemical class 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 230000000701 neuroleptic effect Effects 0.000 description 4
- 230000001624 sedative effect Effects 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 230000004622 sleep time Effects 0.000 description 3
- 238000007920 subcutaneous administration Methods 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical class C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 2
- DHRIQUVLTBDDEP-UHFFFAOYSA-N 2-[1-(3-phenoxazin-10-ylpropyl)piperidin-4-yl]ethanol Chemical compound C1CC(CCO)CCN1CCCN1C2=CC=CC=C2OC2=CC=CC=C21 DHRIQUVLTBDDEP-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- MFESCIUQSIBMSM-UHFFFAOYSA-N I-BCP Chemical compound ClCCCBr MFESCIUQSIBMSM-UHFFFAOYSA-N 0.000 description 2
- KLBQZWRITKRQQV-UHFFFAOYSA-N Thioridazine Chemical compound C12=CC(SC)=CC=C2SC2=CC=CC=C2N1CCC1CCCCN1C KLBQZWRITKRQQV-UHFFFAOYSA-N 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- ZPEIMTDSQAKGNT-UHFFFAOYSA-N chlorpromazine Chemical compound C1=C(Cl)C=C2N(CCCN(C)C)C3=CC=CC=C3SC2=C1 ZPEIMTDSQAKGNT-UHFFFAOYSA-N 0.000 description 2
- 229960001076 chlorpromazine Drugs 0.000 description 2
- 239000012259 ether extract Substances 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 239000000932 sedative agent Substances 0.000 description 2
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 229960002784 thioridazine Drugs 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- ICFFSQKZBUZAQY-UHFFFAOYSA-N 1-(10H-phenoxazin-3-yl)ethanone Chemical class C(C)(=O)C=1C=CC=2NC3=CC=CC=C3OC2C1 ICFFSQKZBUZAQY-UHFFFAOYSA-N 0.000 description 1
- YYTSGNJTASLUOY-UHFFFAOYSA-N 1-chloropropan-2-ol Chemical compound CC(O)CCl YYTSGNJTASLUOY-UHFFFAOYSA-N 0.000 description 1
- VIOXGDDWUXTAJH-UHFFFAOYSA-N 10-(3-piperidin-1-ylpropyl)phenoxazine Chemical compound C12=CC=CC=C2OC2=CC=CC=C2N1CCCN1CCCCC1 VIOXGDDWUXTAJH-UHFFFAOYSA-N 0.000 description 1
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 1
- DGTVTTNTHLZNST-UHFFFAOYSA-N 2-[1-(3-chloropropyl)piperidin-4-yl]ethanol Chemical compound OCCC1CCN(CCCCl)CC1 DGTVTTNTHLZNST-UHFFFAOYSA-N 0.000 description 1
- IWZUQPSFMNVFAD-UHFFFAOYSA-N C(CC)(=O)C=1C=CC=2NC3=CC=CC=C3OC=2C=1 Chemical compound C(CC)(=O)C=1C=CC=2NC3=CC=CC=C3OC=2C=1 IWZUQPSFMNVFAD-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 208000028017 Psychotic disease Diseases 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000003176 neuroleptic agent Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 238000001050 pharmacotherapy Methods 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000000506 psychotropic effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- KEAYESYHFKHZAL-IGMARMGPSA-N sodium-23 atom Chemical compound [23Na] KEAYESYHFKHZAL-IGMARMGPSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen 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)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL121420D NL121420C (enrdf_load_stackoverflow) | 1962-04-17 | ||
| NL291542D NL291542A (enrdf_load_stackoverflow) | 1962-04-17 | ||
| BE631122D BE631122A (enrdf_load_stackoverflow) | 1962-04-17 | ||
| DEB66847A DE1212537B (de) | 1962-04-17 | 1962-04-17 | Verfahren zur Herstellung basischer Phenoxazinderivate und ihrer Salze |
| GB1191463A GB968182A (en) | 1962-04-17 | 1963-03-26 | New basic phenoxazine derivatives |
| CH455863A CH421961A (de) | 1962-04-17 | 1963-04-10 | Verfahren zur Herstellung neuer basischer Phenoxazin-Derivate und ihrer Salze |
| LU43547D LU43547A1 (enrdf_load_stackoverflow) | 1962-04-17 | 1963-04-12 | |
| FR931628A FR1355946A (fr) | 1962-04-17 | 1963-04-16 | Procédé pour la préparation de nouveaux dérivés basiques de la phénoxazine, ainsi que de leurs sels |
| DK561065A DK108029C (da) | 1962-04-17 | 1963-04-16 | Fremgangsmåde til fremstilling af basiske fenoksazinderivater eller salte deraf. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB66847A DE1212537B (de) | 1962-04-17 | 1962-04-17 | Verfahren zur Herstellung basischer Phenoxazinderivate und ihrer Salze |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1212537B true DE1212537B (de) | 1966-03-17 |
Family
ID=6975289
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEB66847A Pending DE1212537B (de) | 1962-04-17 | 1962-04-17 | Verfahren zur Herstellung basischer Phenoxazinderivate und ihrer Salze |
Country Status (7)
| Country | Link |
|---|---|
| BE (1) | BE631122A (enrdf_load_stackoverflow) |
| CH (1) | CH421961A (enrdf_load_stackoverflow) |
| DE (1) | DE1212537B (enrdf_load_stackoverflow) |
| DK (1) | DK108029C (enrdf_load_stackoverflow) |
| GB (1) | GB968182A (enrdf_load_stackoverflow) |
| LU (1) | LU43547A1 (enrdf_load_stackoverflow) |
| NL (2) | NL121420C (enrdf_load_stackoverflow) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE569697A (enrdf_load_stackoverflow) * | ||||
| GB850334A (en) * | 1957-08-14 | 1960-10-05 | Pfizer & Co C | Phenoxazine derivatives and preparation thereof |
-
0
- NL NL291542D patent/NL291542A/xx unknown
- NL NL121420D patent/NL121420C/xx active
- BE BE631122D patent/BE631122A/xx unknown
-
1962
- 1962-04-17 DE DEB66847A patent/DE1212537B/de active Pending
-
1963
- 1963-03-26 GB GB1191463A patent/GB968182A/en not_active Expired
- 1963-04-10 CH CH455863A patent/CH421961A/de unknown
- 1963-04-12 LU LU43547D patent/LU43547A1/xx unknown
- 1963-04-16 DK DK561065A patent/DK108029C/da active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE569697A (enrdf_load_stackoverflow) * | ||||
| GB850334A (en) * | 1957-08-14 | 1960-10-05 | Pfizer & Co C | Phenoxazine derivatives and preparation thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| NL121420C (enrdf_load_stackoverflow) | |
| GB968182A (en) | 1964-08-26 |
| NL291542A (enrdf_load_stackoverflow) | |
| LU43547A1 (enrdf_load_stackoverflow) | 1963-06-12 |
| BE631122A (enrdf_load_stackoverflow) | |
| CH421961A (de) | 1966-10-15 |
| DK108029C (da) | 1967-08-07 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1795183B1 (de) | 5,11-Dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-on-derivate und Arzneimittel | |
| DE69126433T2 (de) | 1,4-disubstituierte piperazine | |
| DE1018422B (de) | Verfahren zur Herstellung basisch substituierter Heterocyclen | |
| DE1159954B (de) | Verfahren zur Herstellung neuer 10-(Alkoxypiperidinopropyl)-phenthiazine und ihrer Salze | |
| DE1670772B2 (de) | 4h-3,1-benzoxazin-derivate, deren salze und pharmazeutische praeparate | |
| DE2426149B2 (de) | 7-Fluor-substituierte Phenothiazine, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Mittel | |
| DE1795176C3 (de) | hT-substituierte 5-Aminoacetyl-5,10-dihydro-l lH-dibenzo eckige Klammer auf b,e eckige Klammer zu eckige Klammer auf 1,4 eckige Klammer zu diazepin-11one und Verfahren zu ihrer Herstellung | |
| DE2117358C3 (de) | 4'-Aminomethyl-spiro eckige Klammer auf dibenzo eckige Klammer auf a,d eckige Klammer zu cycloheptadi-(oder tri-) en-5,2'-(1 \3'-dioxolan) eckige Klammer zu -Derivate, Verfahren zu deren Herstellung und diese Verbindungen enthaltene Arzneimittel | |
| DE2724478C2 (de) | 5,11-Dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-on-derivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel | |
| DE1212537B (de) | Verfahren zur Herstellung basischer Phenoxazinderivate und ihrer Salze | |
| DE1115259B (de) | Verfahren zur Herstellung von Iminodibenzylen | |
| DE2528194C2 (de) | Benzhydryloxyäthylamin-Derivate, deren Salze, Verfahren zur Herstellung derselben und solche enthaltende Arzneimittel | |
| DE2029185C3 (de) | 2H-l,3,4,6,7,8,9Heptahydro-2-azachinolizyl-(2) geschweifte Klammer zu -äthyl] -phenthiazin, seine Säureadditionssalze, Verfahren zu deren Herstellung und Arzneimittel | |
| DE1095836B (de) | Verfahren zur Herstellung von in 10-Stellung basisch substituierten Phenthiazinderivaten | |
| DE2144077A1 (de) | Neue Piperazindenvate und Ver fahren zu deren Herstellung | |
| DE1931487C3 (de) | In 5-Stellung substituierte 5,10-Dihydro-11H-dibenzo eckige Klammer auf b,e eckige Klammer zu eckige Klammer auf 1,4 eckige Klammer zu diazepin-11 -one und Verfahren zu ihrer Herstellung | |
| DE1645901C3 (de) | gamma-(4-Alkylp!peridino)-p-fluorbutyrophenone und Verfahren zu ihrer Herstellung | |
| DE1131679B (de) | Verfahren zur Herstellung von Phenthiazinverbindungen | |
| DE1936670C3 (de) | S-Diallylaminoalkanoyl-SJO-dihydro-11H-dibenzo eckige Klammer auf b,e eckige Klammer zu- eckige Klammer auf 1,4 eckige Klammer zu diazepin-11-onderivate | |
| AT233577B (de) | Verfahren zur Herstellung neuer, basischer Phenoxazin-Derivate und ihrer Salze | |
| DE1445416C3 (de) | N-substituierte 23-Polymethylenindole, ein Verfahren zu ihrer Herstellung und Arzneimittel | |
| DE2215545C3 (de) | Pyridin-2-carbonsäurepiperazide | |
| AT256835B (de) | Verfahren zur Herstellung von neuen Aminoalkyl-substituierten 5-gliedrigen Heterocyclen und ihren Salzen | |
| AT211001B (de) | Verfahren zur Herstellung von neuen Scopin-äthern | |
| DE1168434B (de) | Verfahren zur Herstellung von 10-(3'-Piperazinopropyl)-phenthiazinverbindungen |