CH494242A - Verfahren zur Herstellung von neuen Estern der 10-Piperazino-10,11-dihydrodibenzo (b,f)thiepin-Reihe - Google Patents
Verfahren zur Herstellung von neuen Estern der 10-Piperazino-10,11-dihydrodibenzo (b,f)thiepin-ReiheInfo
- Publication number
- CH494242A CH494242A CH1627267A CH1627267A CH494242A CH 494242 A CH494242 A CH 494242A CH 1627267 A CH1627267 A CH 1627267A CH 1627267 A CH1627267 A CH 1627267A CH 494242 A CH494242 A CH 494242A
- Authority
- CH
- Switzerland
- Prior art keywords
- dihydrodibenzo
- general formula
- piperazino
- thiepin
- benzene
- Prior art date
Links
- 150000002148 esters Chemical class 0.000 title claims abstract description 6
- 150000003839 salts Chemical class 0.000 claims abstract description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 36
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 238000006386 neutralization reaction Methods 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- 230000010933 acylation Effects 0.000 claims description 2
- 238000005917 acylation reaction Methods 0.000 claims description 2
- 150000008064 anhydrides Chemical class 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 150000007522 mineralic acids Chemical class 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 235000005985 organic acids Nutrition 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 150000001735 carboxylic acids Chemical class 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims 1
- 150000008282 halocarbons Chemical class 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 6
- IUJDSEJGGMCXSG-UHFFFAOYSA-N Thiopental Chemical compound CCCC(C)C1(CC)C(=O)NC(=S)NC1=O IUJDSEJGGMCXSG-UHFFFAOYSA-N 0.000 abstract description 3
- 201000000980 schizophrenia Diseases 0.000 abstract description 3
- 229960003279 thiopental Drugs 0.000 abstract description 3
- 230000000891 anti-reserpine Effects 0.000 abstract description 2
- 208000010513 Stupor Diseases 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- -1 alkyl radical Chemical group 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 5
- 239000011976 maleic acid Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- FWWOWPGPERBCNJ-UHFFFAOYSA-N 2-hydroxy-4-(2-hydroxyethoxy)-4-oxobutanoic acid Chemical compound OCCOC(=O)CC(O)C(O)=O FWWOWPGPERBCNJ-UHFFFAOYSA-N 0.000 description 4
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 4
- 239000012346 acetyl chloride Substances 0.000 description 4
- 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 4
- 229960001076 chlorpromazine Drugs 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- 241000699666 Mus <mouse, genus> Species 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- 235000011114 ammonium hydroxide Nutrition 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- DBQYUWWOBWTUPV-UHFFFAOYSA-N 5,6-dihydrobenzo[b][1]benzothiepine Chemical compound C1CC2=CC=CC=C2SC2=CC=CC=C12 DBQYUWWOBWTUPV-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 206010002091 Anaesthesia Diseases 0.000 description 2
- 230000037005 anaesthesia Effects 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 238000013016 damping Methods 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 230000003472 neutralizing effect Effects 0.000 description 2
- 208000020016 psychiatric disease Diseases 0.000 description 2
- NYABMDNSLNOWKJ-UHFFFAOYSA-N 3-[4-(3-chloro-5,6-dihydrobenzo[b][1]benzothiepin-5-yl)piperazin-1-yl]propan-1-ol Chemical compound C1CN(CCCO)CCN1C1C2=CC(Cl)=CC=C2SC2=CC=CC=C2C1 NYABMDNSLNOWKJ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 230000002903 catalepsic effect Effects 0.000 description 1
- 239000003874 central nervous system depressant Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229910052593 corundum Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 231100000518 lethal Toxicity 0.000 description 1
- 230000001665 lethal effect Effects 0.000 description 1
- 230000007774 longterm Effects 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
- 239000012074 organic phase Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 229910001845 yogo sapphire Inorganic materials 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
- C07D337/00—Heterocyclic compounds containing rings of more than six members having one sulfur atom as the only ring hetero atom
- C07D337/02—Seven-membered rings
- C07D337/06—Seven-membered rings condensed with carbocyclic rings or ring systems
- C07D337/10—Seven-membered rings condensed with carbocyclic rings or ring systems condensed with two six-membered rings
- C07D337/14—[b,f]-condensed
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS758866 | 1966-11-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH494242A true CH494242A (de) | 1970-07-31 |
Family
ID=5425335
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1627267A CH494242A (de) | 1966-11-29 | 1967-11-21 | Verfahren zur Herstellung von neuen Estern der 10-Piperazino-10,11-dihydrodibenzo (b,f)thiepin-Reihe |
Country Status (9)
| Country | Link |
|---|---|
| AT (1) | AT273141B (enrdf_load_stackoverflow) |
| BE (1) | BE707068A (enrdf_load_stackoverflow) |
| CH (1) | CH494242A (enrdf_load_stackoverflow) |
| DE (1) | DE1695798A1 (enrdf_load_stackoverflow) |
| DK (1) | DK115404B (enrdf_load_stackoverflow) |
| FR (1) | FR1559664A (enrdf_load_stackoverflow) |
| GB (1) | GB1136527A (enrdf_load_stackoverflow) |
| NL (1) | NL6716220A (enrdf_load_stackoverflow) |
| SE (1) | SE318881B (enrdf_load_stackoverflow) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE757926A (fr) * | 1969-10-25 | 1971-04-01 | Spofa Usines Pharma Reunies | Procede de preparation de nouvelles amidoximes de la serie des 10-piperazino-10,11-dihydrodibenzo/b,f/thiepines et leurs sels, ainsique les produits obtenus |
| BE759278A (fr) * | 1969-11-25 | 1971-04-30 | Spofa Usines Pharma Reunies | Procede de preparation des nouveaux esters de la serie de 10-piperazino-10, 11-dihydrodibenzo/b,f/ thiepines et de leurs sels, ainsi que les produits obtenus |
| CH554362A (de) * | 1970-07-30 | 1974-09-30 | Spofa Vereinigte Pharma Werke | Verfahren zur herstellung von neuen estern tricyklischer piperazinoalkanole. |
-
1967
- 1967-11-21 DE DE19671695798 patent/DE1695798A1/de active Pending
- 1967-11-21 CH CH1627267A patent/CH494242A/de not_active IP Right Cessation
- 1967-11-24 BE BE707068D patent/BE707068A/xx unknown
- 1967-11-28 SE SE16320/67A patent/SE318881B/xx unknown
- 1967-11-28 AT AT1074267A patent/AT273141B/de active
- 1967-11-29 NL NL6716220A patent/NL6716220A/xx unknown
- 1967-11-29 DK DK597667A patent/DK115404B/da unknown
- 1967-11-29 FR FR1559664D patent/FR1559664A/fr not_active Expired
- 1967-11-29 GB GB5425767A patent/GB1136527A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| AT273141B (de) | 1969-08-11 |
| BE707068A (enrdf_load_stackoverflow) | 1968-04-01 |
| GB1136527A (en) | 1968-12-11 |
| NL6716220A (enrdf_load_stackoverflow) | 1968-05-30 |
| DE1695798A1 (de) | 1972-03-02 |
| SE318881B (enrdf_load_stackoverflow) | 1969-12-22 |
| DK115404B (da) | 1969-10-06 |
| FR1559664A (enrdf_load_stackoverflow) | 1969-03-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |