CH585222A5 - Prepn. of antipsychotic heterocyclic piperazine derivs. - by reaction of heterocyclic ketones with metal piperazine complexes - Google Patents
Prepn. of antipsychotic heterocyclic piperazine derivs. - by reaction of heterocyclic ketones with metal piperazine complexesInfo
- Publication number
- CH585222A5 CH585222A5 CH208273A CH208273A CH585222A5 CH 585222 A5 CH585222 A5 CH 585222A5 CH 208273 A CH208273 A CH 208273A CH 208273 A CH208273 A CH 208273A CH 585222 A5 CH585222 A5 CH 585222A5
- Authority
- CH
- Switzerland
- Prior art keywords
- piperazine
- heterocyclic
- alkyl
- formula
- prepn
- Prior art date
Links
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 title abstract 6
- -1 heterocyclic ketones Chemical class 0.000 title abstract 3
- 230000000561 anti-psychotic effect Effects 0.000 title abstract 2
- 125000000623 heterocyclic group Chemical group 0.000 title abstract 2
- 229910052751 metal Inorganic materials 0.000 title abstract 2
- 239000002184 metal Substances 0.000 title abstract 2
- 150000004885 piperazines Chemical class 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 6
- 229910052736 halogen Inorganic materials 0.000 abstract 3
- 150000002367 halogens Chemical class 0.000 abstract 3
- 125000004414 alkyl thio group Chemical group 0.000 abstract 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 2
- QPPOMEOQNLTFRU-UHFFFAOYSA-N 1,4-thiazepine Chemical compound S1C=CC=NC=C1 QPPOMEOQNLTFRU-UHFFFAOYSA-N 0.000 abstract 1
- KAAZGXDPUNNEFN-UHFFFAOYSA-N Clotiapine Chemical compound C1CN(C)CCN1C1=NC2=CC=CC=C2SC2=CC=C(Cl)C=C12 KAAZGXDPUNNEFN-UHFFFAOYSA-N 0.000 abstract 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 abstract 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 239000000164 antipsychotic agent Substances 0.000 abstract 1
- 229940005529 antipsychotics Drugs 0.000 abstract 1
- 150000008038 benzoazepines Chemical class 0.000 abstract 1
- 229960003864 clotiapine Drugs 0.000 abstract 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
- 239000003326 hypnotic agent Substances 0.000 abstract 1
- 230000000147 hypnotic effect Effects 0.000 abstract 1
- 229940035363 muscle relaxants Drugs 0.000 abstract 1
- 239000003158 myorelaxant agent Substances 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000000932 sedative agent Substances 0.000 abstract 1
- 229940125723 sedative agent Drugs 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 abstract 1
- 229910052720 vanadium Inorganic materials 0.000 abstract 1
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/22—Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Prepn. of heterocyclic piperazine derivs. of formula (I) comprises reacting a heterocyclic ketone of formula (II) with a Gp.IVb metal or vanadium complex of a piperazine deriv. of formula (III): where R1 is H, 2-6C alkoxyalkyl, 1-4C alkyl or opt. acylated 1-4C hydroxyalkyl. R4 is H, 1-4C alkyl, alkoxy or alkylthio, halogen or CF3. A is a gp. of formula Z1 or Z2: X is CH2, O, S, NH or N(1-3C alkyl) when A=Z1, or X is CH2 or S when A=Z2. R2 is H, 1-4C alkyl, di(1-4C alkyl)sulphamoyl, 1-4C alkylsulphonyl alkoxy or alkylthio, halogen, NO2, CF3SO2, CF3O, CF3S, MeCO, CN or CF3. R3 is H, halogen or 1-4C alkyl. Cpds. (I) are largely known, e.g. 2-chloro-11-(4-methyl-1-piperazinyl)-dibenzo b, f 1, 4 thiazepine is the antipsychotic clothiapin. The new cpds. (I), esp. the 10H-thieno 3, 2-C benzazepines, can be used as antipsychotics, sedatives, hypnotics and muscle relaxants.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH208273A CH585222A5 (en) | 1973-02-14 | 1973-02-14 | Prepn. of antipsychotic heterocyclic piperazine derivs. - by reaction of heterocyclic ketones with metal piperazine complexes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH208273A CH585222A5 (en) | 1973-02-14 | 1973-02-14 | Prepn. of antipsychotic heterocyclic piperazine derivs. - by reaction of heterocyclic ketones with metal piperazine complexes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH585222A5 true CH585222A5 (en) | 1977-02-28 |
Family
ID=4225477
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH208273A CH585222A5 (en) | 1973-02-14 | 1973-02-14 | Prepn. of antipsychotic heterocyclic piperazine derivs. - by reaction of heterocyclic ketones with metal piperazine complexes |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH585222A5 (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0001401A1 (en) * | 1977-09-29 | 1979-04-18 | Sandoz Ag | Thienobenzazepine derivatives, processes for their production and pharmaceutical compositions containing them |
| US5607929A (en) * | 1991-05-02 | 1997-03-04 | Glaxo Wellcome Inc. | Antiviral dibenzothiazepinone derivatives |
| WO2007053618A1 (en) * | 2005-10-31 | 2007-05-10 | Acadia Pharmaceuticals Inc. | Prodrugs of muscarinic agonists and methods of treatment of neuropsychiatric disorders |
| US7491715B2 (en) | 2003-12-22 | 2009-02-17 | Acadia Pharmaceuticals, Inc. | Amino substituted diaryl[a,d]cycloheptene analogs as muscarinic agonists and methods of treatment of neuropsychiatric disorders |
| US7582661B2 (en) | 2002-11-18 | 2009-09-01 | Chemocentryx, Inc. | Aryl sulfonamides |
| US7999109B2 (en) | 2002-05-24 | 2011-08-16 | Millennium Pharmaceuticals, Inc. | CCR9 inhibitors and methods of use thereof |
-
1973
- 1973-02-14 CH CH208273A patent/CH585222A5/en not_active IP Right Cessation
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0001401A1 (en) * | 1977-09-29 | 1979-04-18 | Sandoz Ag | Thienobenzazepine derivatives, processes for their production and pharmaceutical compositions containing them |
| US5607929A (en) * | 1991-05-02 | 1997-03-04 | Glaxo Wellcome Inc. | Antiviral dibenzothiazepinone derivatives |
| US7999109B2 (en) | 2002-05-24 | 2011-08-16 | Millennium Pharmaceuticals, Inc. | CCR9 inhibitors and methods of use thereof |
| US8030517B2 (en) | 2002-05-24 | 2011-10-04 | Millennium Pharmaceuticals, Inc. | CCR9 inhibitors and methods of use thereof |
| US9035096B2 (en) | 2002-05-24 | 2015-05-19 | Millennium Pharmaceuticals, Inc. | CCR9 inhibitors and methods of use thereof |
| US7582661B2 (en) | 2002-11-18 | 2009-09-01 | Chemocentryx, Inc. | Aryl sulfonamides |
| US8211896B2 (en) | 2002-11-18 | 2012-07-03 | Chemocentryx, Inc. | Aryl sulfonamides |
| US7491715B2 (en) | 2003-12-22 | 2009-02-17 | Acadia Pharmaceuticals, Inc. | Amino substituted diaryl[a,d]cycloheptene analogs as muscarinic agonists and methods of treatment of neuropsychiatric disorders |
| US7517871B2 (en) | 2003-12-22 | 2009-04-14 | Acadia Pharmaceuticals, Inc. | Amino substituted diaryl[a,d]cycloheptene analogs as muscarinic agonists and methods of treatment of neuropsychiatric disorders |
| US7550454B2 (en) | 2003-12-22 | 2009-06-23 | Acadia Pharmaceuticals, Inc. | Amino substituted diaryl[a,d]cycloheptene analogs as muscarinic agonists and methods of treatment of neuropsychiatric disorders |
| US7622461B2 (en) | 2003-12-22 | 2009-11-24 | Acadia Pharmaceuticals Inc. | Amino substituted diaryl[a,d]cycloheptene analogs as muscarinic agonists and methods of treatment of neuropsychiatric disorders |
| WO2007053618A1 (en) * | 2005-10-31 | 2007-05-10 | Acadia Pharmaceuticals Inc. | Prodrugs of muscarinic agonists and methods of treatment of neuropsychiatric disorders |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Mukerjee et al. | Isothiocyanates in the chemistry of heterocycles | |
| CH585222A5 (en) | Prepn. of antipsychotic heterocyclic piperazine derivs. - by reaction of heterocyclic ketones with metal piperazine complexes | |
| MX9704646A (en) | 3-aryl-tetronic acid derivatives, the production thereof and the use thereof as anti-parasitic agents. | |
| ATE11781T1 (en) | PHARMACEUTICAL PREPARATIONS CONTAINING SPIROSUCCINIMIDE DERIVATIVES. | |
| HUP9801704A2 (en) | Pyrido[2,3-d]pyrimidines for inhibiting protein tyrosine kinase mediated cellular proliferation and medicaments containing them | |
| ATE272063T1 (en) | RAPAMYCIN DERIVATIVES AND THEIR USE, IN PARTICULAR AS IMMUNOSUPPRESSORS | |
| ES2031892T3 (en) | ANTI-ALLERGIC AND ANTI-INFLAMMATORY AGENTS. | |
| FR2110283A1 (en) | 2-phenyl-as-triazine-3,4 (2h,4h)-dione derivs - having coccidiostatic activity | |
| HUP0204354A2 (en) | Novel heterocyclic derivatives, preparation method and pharmaceutical compositions containing same and their use | |
| ES2129220T3 (en) | 1-AMINO-1,2,3-TRIAZOL PRODUCTION PROCEDURE. | |
| PL300804A1 (en) | Substituted (pydidinylamino)-benzisoxazoles and benzo[b]thiophenes, methods of obtaining sames and their application as medicines | |
| DE69031845D1 (en) | 6,11-Dihydro-5H-pyrido (2,3-b) (1,5) benzodiazepin-5-one and thione and their use for the prevention or treatment of AIDS | |
| FR2222102A1 (en) | 11-Piperazino dibenzo diazepines neuroleptics - and anti-depressants, prepd. from a dibenzo diazepin-11-one and a piperazine | |
| PT86197A (en) | Fused heterocyclic tetrahydroaminoquinolinols and related compounds a process for their preparation and their use as medicaments | |
| ES8304958A1 (en) | Aromatic compounds, processes for their preparation and their use. | |
| ATE171621T1 (en) | USE OF 2-PHENYL-1,2-BENZISOSELENAZOL-3(2H)-ONE | |
| GB1510270A (en) | Process for producing 2(1h)-quinazolinones or-thiones | |
| FR2356643A1 (en) | 5-0-ACYL-IMIDAZOLE-4-CARBOXAMIDES, THEIR OBTAINING AND PHARMACEUTICAL COMPOSITION IN CONTAINER | |
| DE59003823D1 (en) | Substituted N-hydroxypyrazoles and fungicides containing these compounds. | |
| DE3780649D1 (en) | CONDENSED BENZAZEPINE. | |
| FR2809001B1 (en) | COMPOSITIONS FOR THE OXIDIZING DYE OF KERATINIC FIBERS CONTAINING AT LEAST 5-METHYL PYRAZOLO- [1,5-a] -PYRIMIDINE-3,7-DIAMINE AS OXIDIZING BASE; DYING PROCESSES IMPLEMENTED | |
| FR2300090A1 (en) | Tetrahydro-thieno-pyridine derivs. prepn. - by cyclizing 2-(2-aminoethyl)thiophenes with formaldehyde (BE060876) | |
| BE812742A (en) | 11-Piperazino dibenzo diazepines neuroleptics - and anti-depressants, prepd. from a dibenzo diazepin-11-one and a piperazine | |
| FI912499A0 (en) | PYRIDO / 3,4-B / PYRROLO / 1,2-E // 1,4,5 / OXADIAZEPINER OCH DAERMED ANALOGER OF NAERBESLAEKTADE, FOERFARANDE FOER DERAS FRAMSTAELLNING OCH DERAS ANVAENDNING SOM LAEKEMEDEL. | |
| FR2319642A2 (en) | Tetrahydro-thieno-pyridine derivs. prepn. - by cyclizing 2-(2-aminoethyl)thiophenes with formaldehyde (BE060876) |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |