GB805778A - Improvements in or relating to piperazine derivatives - Google Patents
Improvements in or relating to piperazine derivativesInfo
- Publication number
- GB805778A GB805778A GB16753/57A GB1675357A GB805778A GB 805778 A GB805778 A GB 805778A GB 16753/57 A GB16753/57 A GB 16753/57A GB 1675357 A GB1675357 A GB 1675357A GB 805778 A GB805778 A GB 805778A
- Authority
- GB
- United Kingdom
- Prior art keywords
- phenothiazine
- chloro
- piperazine
- propyl
- acetoxyethyl
- 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
- 150000004885 piperazines Chemical class 0.000 title 1
- 229940066771 systemic antihistamines piperazine derivative Drugs 0.000 title 1
- 229950000688 phenothiazine Drugs 0.000 abstract 9
- -1 acetyl halide Chemical class 0.000 abstract 6
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 abstract 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 abstract 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 abstract 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 abstract 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Substances OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 abstract 2
- AVMHMVJVHYGDOO-NSCUHMNNSA-N (e)-1-bromobut-2-ene Chemical compound C\C=C\CBr AVMHMVJVHYGDOO-NSCUHMNNSA-N 0.000 abstract 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 abstract 1
- VZIQXGLTRZLBEX-UHFFFAOYSA-N 2-chloro-1-propanol Chemical compound CC(Cl)CO VZIQXGLTRZLBEX-UHFFFAOYSA-N 0.000 abstract 1
- KFZGLJSYQXZIGP-UHFFFAOYSA-N 2-chloro-10h-phenothiazine Chemical compound C1=CC=C2NC3=CC(Cl)=CC=C3SC2=C1 KFZGLJSYQXZIGP-UHFFFAOYSA-N 0.000 abstract 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 abstract 1
- USEGQJLHQSTGHW-UHFFFAOYSA-N 3-bromo-2-methylprop-1-ene Chemical group CC(=C)CBr USEGQJLHQSTGHW-UHFFFAOYSA-N 0.000 abstract 1
- PXRKCOCTEMYUEG-UHFFFAOYSA-N 5-aminoisoindole-1,3-dione Chemical compound NC1=CC=C2C(=O)NC(=O)C2=C1 PXRKCOCTEMYUEG-UHFFFAOYSA-N 0.000 abstract 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 abstract 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 abstract 1
- 239000005977 Ethylene Substances 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- 230000000397 acetylating effect Effects 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical group BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 229960005070 ascorbic acid Drugs 0.000 abstract 1
- 235000010323 ascorbic acid Nutrition 0.000 abstract 1
- 239000011668 ascorbic acid Substances 0.000 abstract 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 abstract 1
- 229940073608 benzyl chloride Drugs 0.000 abstract 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 abstract 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical group COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 abstract 1
- ANNNGOUEZBONHD-UHFFFAOYSA-N ethyl phenylmethanesulfonate Chemical compound CCOS(=O)(=O)CC1=CC=CC=C1 ANNNGOUEZBONHD-UHFFFAOYSA-N 0.000 abstract 1
- 229940093915 gynecological organic acid Drugs 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- CZXGXYBOQYQXQD-UHFFFAOYSA-N methyl benzenesulfonate Chemical compound COS(=O)(=O)C1=CC=CC=C1 CZXGXYBOQYQXQD-UHFFFAOYSA-N 0.000 abstract 1
- 229940050176 methyl chloride Drugs 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 150000007522 mineralic acids Chemical class 0.000 abstract 1
- 150000007524 organic acids Chemical class 0.000 abstract 1
- 235000005985 organic acids Nutrition 0.000 abstract 1
- 150000002895 organic esters Chemical class 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 150000003839 salts Chemical group 0.000 abstract 1
- 235000009518 sodium iodide Nutrition 0.000 abstract 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D279/10—1,4-Thiazines; Hydrogenated 1,4-thiazines
- C07D279/14—1,4-Thiazines; Hydrogenated 1,4-thiazines condensed with carbocyclic rings or ring systems
- C07D279/18—[b, e]-condensed with two six-membered rings
- C07D279/22—[b, e]-condensed with two six-membered rings with carbon atoms directly attached to the ring nitrogen atom
- C07D279/24—[b, e]-condensed with two six-membered rings with carbon atoms directly attached to the ring nitrogen atom with hydrocarbon radicals, substituted by amino radicals, attached to the ring nitrogen atom
- C07D279/28—[b, e]-condensed with two six-membered rings with carbon atoms directly attached to the ring nitrogen atom with hydrocarbon radicals, substituted by amino radicals, attached to the ring nitrogen atom with other substituents attached to the ring system
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US592745A US2766235A (en) | 1956-06-21 | 1956-06-21 | N-(beta-acetoxyethyl)-n'-(chlorophenothiazinepropyl) piperazine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB805778A true GB805778A (en) | 1958-12-10 |
Family
ID=24371897
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB16753/57A Expired GB805778A (en) | 1956-06-21 | 1957-05-27 | Improvements in or relating to piperazine derivatives |
Country Status (4)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1174320B (de) * | 1959-12-11 | 1964-07-23 | Egyt Gyogyszervegyeszeti Gyar | Verfahren zur Herstellung von Estern des 3-Chlor-10-{3'-[4''-(ª‰-oxyaethyl)-piperazino]-propyl}-phenthiazins |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3047572A (en) * | 1962-07-31 | Dimethylaminophenotfflazine | ||
| GB833473A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1955-03-19 | |||
| CH365379A (de) * | 1956-04-18 | 1962-11-15 | Sandoz Ag | Verfahren zur Herstellung von neuen, in 3-Stellung mit einer einwertigen Schwefelfunktion substituierten Phenothiazinen |
| US2985654A (en) * | 1956-08-09 | 1961-05-23 | Schering Corp | Piperazino derivatives and methods for their manufacture |
| US2860138A (en) * | 1956-11-21 | 1958-11-11 | Schering Corp | Carbamate esters of hydroxyalkyl piperazino alkyl phenothiazines |
| CH356775A (fr) * | 1956-12-13 | 1961-09-15 | Scherico Ltd | Procédé de préparation de composés thérapeutiques |
| FR1186175A (fr) * | 1956-12-27 | 1959-08-17 | Rhone Poulenc Sa | Nouveaux dérivés nu-pipéraziniques substitués de la cyano-3 phénothiazine et leur préparation |
| FR1186182A (fr) * | 1957-01-15 | 1959-08-17 | Rhone Poulenc Sa | Nouveaux dérivés nu-pipéraziniques substitués de la substituée-3 phénothiazine et leurs procédés de préparation |
| NL58901C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1957-02-07 | 1947-02-15 | ||
| DE1071087B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1957-04-11 | 1959-12-17 | ||
| US3058979A (en) * | 1957-05-13 | 1962-10-16 | Smith Kline French Lab | New perfluoroalkylphenothiazine derivatives |
| DE1173099B (de) * | 1957-06-10 | 1964-07-02 | Smith Kline French Lab | Verfahren zur Herstellung von in 10-Stellung basisch substituierten Trifluormethylsulfonyl-phenthiazinen |
| DE1181709B (de) * | 1957-06-18 | 1964-11-19 | Smith Kline French Lab | Verfahren zur Herstellung von in 10-Stellung basisch substituierten Phenthiazinen |
| BE561550A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1957-08-23 | |||
| BE568837A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1957-09-11 | 1900-01-01 | ||
| FR1212723A (fr) * | 1958-01-09 | 1960-03-25 | Rhone Poulenc Sa | Nouveaux dérivés de la phénothiazine à chaîne carbamoylpipérazine et leur préparation |
| DE1132136B (de) * | 1958-01-24 | 1962-06-28 | Rhone Poulenc Sa | Verfahren zur Herstellung von Phenthiazinverbindungen |
| NL100554C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1958-04-19 | |||
| NL240007A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1958-06-10 | |||
| US3054791A (en) * | 1958-06-30 | 1962-09-18 | Olin Mathieson | 10-piperazinoalkyl substituted trifluoromethylphenothiazines |
| US3082208A (en) * | 1958-07-07 | 1963-03-19 | Sterling Drug Inc | 10-[(1-piperidyl)lower-alkyl]-loweralkanoylphenothiazines |
| US3193549A (en) * | 1958-07-07 | 1965-07-06 | Sterling Drug Inc | 10-[(1-piperidyl)lower-alkyl]-trifluoromethylphenothiazines |
| US3000885A (en) * | 1958-08-07 | 1961-09-19 | Searle & Co | 2-acyl-10-oxyalkylpiperidinoalkylphenothiazines and process |
| GB859727A (en) * | 1958-10-28 | 1961-01-25 | Rhone Poulenc Sa | New phenthiazine derivatives |
| US3081229A (en) * | 1958-12-09 | 1963-03-12 | American Home Prod | Phenothiazines with antihistaminic and antipsychotic activity |
| US3043842A (en) * | 1959-02-09 | 1962-07-10 | Smith Kline French Lab | Substituted acridans |
| DE1160442B (de) * | 1959-03-18 | 1964-01-02 | Degussa | Verfahren zur Herstellung von 3-Trifluormethylphenthiazinen |
| NL109705C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1959-04-17 | |||
| NL120362C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1961-04-26 | |||
| US3325486A (en) * | 1963-05-31 | 1967-06-13 | Egyt Gyogyszervegyeszeti Gyar | Phenthiazine-amide ester derivatives and process for their preparation |
| CN101198323A (zh) * | 2005-04-22 | 2008-06-11 | 惠氏公司 | 用于治疗或预防精神障碍的治疗组合 |
| US9827252B2 (en) | 2012-03-16 | 2017-11-28 | Children's Medical Center Corporation | Calmodulin inhibitors for the treatment of ribosomal disorders and ribosomapathies |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2694705A (en) * | 1954-11-16 | Nx c c ox a a | ||
| GB666457A (en) * | 1948-10-30 | 1952-02-13 | Henri Morren | Carbonyl chlorides and monocarboxyamides of piperazine and process for the preparation thereof |
| CH298685A (fr) * | 1951-06-28 | 1954-05-15 | Rhone Poulenc Chemicals | Procédé de préparation d'un nouveau dérivé de la phénothiazine. |
-
0
- BE BE558008D patent/BE558008A/xx unknown
-
1956
- 1956-06-21 US US592745A patent/US2766235A/en not_active Expired - Lifetime
-
1957
- 1957-05-27 GB GB16753/57A patent/GB805778A/en not_active Expired
- 1957-06-21 DE DES53950A patent/DE1124500B/de active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1174320B (de) * | 1959-12-11 | 1964-07-23 | Egyt Gyogyszervegyeszeti Gyar | Verfahren zur Herstellung von Estern des 3-Chlor-10-{3'-[4''-(ª‰-oxyaethyl)-piperazino]-propyl}-phenthiazins |
Also Published As
| Publication number | Publication date |
|---|---|
| BE558008A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | |
| US2766235A (en) | 1956-10-09 |
| DE1124500B (de) | 1962-03-01 |
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