IE35251L - Dibenzothiepinopyrroles - Google Patents
DibenzothiepinopyrrolesInfo
- Publication number
- IE35251L IE35251L IE710660A IE66071A IE35251L IE 35251 L IE35251 L IE 35251L IE 710660 A IE710660 A IE 710660A IE 66071 A IE66071 A IE 66071A IE 35251 L IE35251 L IE 35251L
- Authority
- IE
- Ireland
- Prior art keywords
- prepared
- thiepin
- tolylthio
- dibenzo
- trifluoro
- Prior art date
Links
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 abstract 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract 1
- MCWNYRHLQJWZKA-UHFFFAOYSA-N 5,6-bis(2-bromoethyl)-3-(trifluoromethyl)benzo[b][1]benzothiepine Chemical compound BrCCC1=C(C2=C(SC3=C1C=CC=C3)C=CC(=C2)C(F)(F)F)CCBr MCWNYRHLQJWZKA-UHFFFAOYSA-N 0.000 abstract 1
- CZTCCTTURZUYGA-UHFFFAOYSA-N 5,6-dimethyl-3-(trifluoromethyl)-6H-benzo[b][1]benzothiepin-5-ol Chemical compound CC1(C(C2=C(SC3=C1C=C(C=C3)C(F)(F)F)C=CC=C2)C)O CZTCCTTURZUYGA-UHFFFAOYSA-N 0.000 abstract 1
- OHKCIXOBHLRXSB-UHFFFAOYSA-N 5,6-dimethyl-3-(trifluoromethyl)benzo[b][1]benzothiepine Chemical compound CC1=C(C)C2=CC(C(F)(F)F)=CC=C2SC2=CC=CC=C12 OHKCIXOBHLRXSB-UHFFFAOYSA-N 0.000 abstract 1
- UHPSNSBQQBRHTI-UHFFFAOYSA-N 6-methyl-3-(trifluoromethyl)-6H-benzo[b][1]benzothiepin-5-one Chemical compound CC1C2=C(SC3=C(C1=O)C=C(C=C3)C(F)(F)F)C=CC=C2 UHPSNSBQQBRHTI-UHFFFAOYSA-N 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 1
- 101100037762 Caenorhabditis elegans rnh-2 gene Proteins 0.000 abstract 1
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 abstract 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical class [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 230000031709 bromination Effects 0.000 abstract 1
- 238000005893 bromination reaction Methods 0.000 abstract 1
- 239000003874 central nervous system depressant Substances 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 230000018044 dehydration Effects 0.000 abstract 1
- 238000006297 dehydration reaction Methods 0.000 abstract 1
- 150000008510 dibenzothiepins Chemical class 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 230000032050 esterification Effects 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 238000011065 in-situ storage Methods 0.000 abstract 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 1
- 230000011987 methylation Effects 0.000 abstract 1
- 238000007069 methylation reaction Methods 0.000 abstract 1
- CQDGTJPVBWZJAZ-UHFFFAOYSA-N monoethyl carbonate Chemical compound CCOC(O)=O CQDGTJPVBWZJAZ-UHFFFAOYSA-N 0.000 abstract 1
- 150000007524 organic acids Chemical class 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000000546 pharmaceutical excipient Substances 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 150000003839 salts Chemical class 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
-
- 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)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
1334945 Dibenzothiepinopyrrole derivatives CIBA-GEIGY AG 25 May 1971 [26 May 1970] 16904/71 Heading C2C Novel compounds of the Formula I wherein R is hydrogen, C 1-6 straight chain alkyl, isopropyl or allyl and pharmaceutically acceptable salts thereof may be prepared either by cyclizing the dibenzothiepin II with RNH 2 or when R is hydrogen hydrolysing a compound IV wherein Z is an acyl radical of an organic acid, an alkoxy carbonyl group or a cyano group. The intermediate 10,11-bis-(bromoethyl)-2- (trifluoromethyl)-dibenzo[b,f]thiepin may be prepared by N-bromosuccinimide bromination of 10,11 - dimethyl - 2 - trifluoromethyl - dibenzo- [b,f]thiepin which is prepared by dehydration of 10,11-dihydro-10,11-dimethyl-8-trifluoromethyldibenzo[b,f]thiepin-10-ol. which in turn is prepared by treating 11-methyl-8-trifluoromethyldibenzo[b,f]thiepin-10(11H)-one. The dibenzothiepinone may be prepared by cyclizing o- (α,α,α-trifluoro-p-tolylthio)-hydratropic acid which may be prepared by methylation followed by hydrolysis of [o-(α,α,α-trifluoro-p-tolylthio)-phenyl]-malonic acid diethyl ester which in turn is prepared by the action of ethyl carbonate on the sodio derivative, formed in situ, of ethyl[o-(α,α,α- trifluoro-p-tolylthio)phenyl] acetate. which is formed by esterification of the free acid. The intermediate 2-ethoxycarbonyl-2,3-dihydro 5-trifluoromethyl-1H-dibenzo[2,3: 6,7] thiepino [4,5c]pyrrole may be prepared by action of ethyl chloroformate on the 2-allyl compound I. Pharmaceutical compositions of the compounds I show central depressant activity when administered orally, parenterally or rectally with the usual excipients.
[GB1334945A]
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH779870A CH531535A (en) | 1970-05-26 | 1970-05-26 | Process for the preparation of new thiepine derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE35251L true IE35251L (en) | 1971-11-25 |
| IE35251B1 IE35251B1 (en) | 1975-12-24 |
Family
ID=4330648
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE660/71A IE35251B1 (en) | 1970-05-26 | 1971-05-25 | New thiepin derivatives and compositions containing same |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US3755357A (en) |
| JP (1) | JPS5411320B1 (en) |
| AT (2) | AT307429B (en) |
| BE (1) | BE767702A (en) |
| CA (1) | CA939354A (en) |
| CH (1) | CH531535A (en) |
| CS (1) | CS172926B2 (en) |
| DE (1) | DE2125892C3 (en) |
| DK (1) | DK127431B (en) |
| ES (1) | ES391524A1 (en) |
| FI (1) | FI50983C (en) |
| FR (1) | FR2100684B1 (en) |
| GB (1) | GB1334945A (en) |
| IE (1) | IE35251B1 (en) |
| IL (1) | IL36917A (en) |
| NL (1) | NL7106926A (en) |
| NO (1) | NO132355C (en) |
| PL (1) | PL81553B1 (en) |
| SE (1) | SE358396B (en) |
| SU (1) | SU389663A3 (en) |
| ZA (1) | ZA713370B (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3859439A (en) * | 1970-05-26 | 1975-01-07 | Ciba Geigy Corp | 2,3-dihydro-5 -trifluoromethyl-1h-dibenzo(2,3:6,7) thiepino (4,5-c) pyrroles as cns-depressants |
| SE7504508L (en) * | 1974-05-10 | 1975-11-11 | Ciba Geigy Ag | NEW HETEROCYCLIC S-IMINO-S-OXIDES. |
| EP0007450A1 (en) * | 1978-07-07 | 1980-02-06 | Ciba-Geigy Ag | Azatetracyclic carbonitriles, their preparation, pharmaceutical compositions containing them and their application |
| DE3069086D1 (en) * | 1979-12-10 | 1984-10-04 | Ciba Geigy Ag | AZATETRACYCLIC CARBONITRILES |
-
1970
- 1970-05-26 CH CH779870A patent/CH531535A/en not_active IP Right Cessation
-
1971
- 1971-05-19 NL NL7106926A patent/NL7106926A/xx not_active Application Discontinuation
- 1971-05-19 DK DK242071AA patent/DK127431B/en unknown
- 1971-05-19 SE SE06522/71A patent/SE358396B/xx unknown
- 1971-05-19 NO NO1906/71A patent/NO132355C/no unknown
- 1971-05-19 US US00145022A patent/US3755357A/en not_active Expired - Lifetime
- 1971-05-19 FI FI711383A patent/FI50983C/en active
- 1971-05-24 CS CS3783A patent/CS172926B2/cs unknown
- 1971-05-24 SU SU1663201A patent/SU389663A3/ru active
- 1971-05-25 IE IE660/71A patent/IE35251B1/en unknown
- 1971-05-25 CA CA113,749A patent/CA939354A/en not_active Expired
- 1971-05-25 AT AT499972A patent/AT307429B/en not_active IP Right Cessation
- 1971-05-25 ES ES391524A patent/ES391524A1/en not_active Expired
- 1971-05-25 ZA ZA713370A patent/ZA713370B/en unknown
- 1971-05-25 IL IL36917A patent/IL36917A/en unknown
- 1971-05-25 JP JP3528971A patent/JPS5411320B1/ja active Pending
- 1971-05-25 DE DE2125892A patent/DE2125892C3/en not_active Expired
- 1971-05-25 AT AT449971A patent/AT307423B/en not_active IP Right Cessation
- 1971-05-25 PL PL1971148351A patent/PL81553B1/pl unknown
- 1971-05-25 GB GB1690471A patent/GB1334945A/en not_active Expired
- 1971-05-26 FR FR7119107A patent/FR2100684B1/fr not_active Expired
- 1971-05-26 BE BE767702A patent/BE767702A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CA939354A (en) | 1974-01-01 |
| CH531535A (en) | 1972-12-15 |
| SE358396B (en) | 1973-07-30 |
| FR2100684A1 (en) | 1972-03-24 |
| AT307429B (en) | 1973-05-25 |
| NO132355B (en) | 1975-07-21 |
| FI50983C (en) | 1976-09-10 |
| NL7106926A (en) | 1971-11-30 |
| NO132355C (en) | 1975-10-29 |
| BE767702A (en) | 1971-11-26 |
| FR2100684B1 (en) | 1975-10-10 |
| PL81553B1 (en) | 1975-08-30 |
| IE35251B1 (en) | 1975-12-24 |
| SU389663A3 (en) | 1973-07-05 |
| CS172926B2 (en) | 1977-01-28 |
| IL36917A0 (en) | 1971-07-28 |
| ZA713370B (en) | 1972-01-26 |
| ES391524A1 (en) | 1973-06-16 |
| DE2125892C3 (en) | 1980-07-03 |
| DE2125892B2 (en) | 1979-10-18 |
| GB1334945A (en) | 1973-10-24 |
| AT307423B (en) | 1973-05-25 |
| DE2125892A1 (en) | 1971-12-09 |
| US3755357A (en) | 1973-08-28 |
| DK127431B (en) | 1973-11-05 |
| FI50983B (en) | 1976-05-31 |
| JPS5411320B1 (en) | 1979-05-14 |
| IL36917A (en) | 1974-03-14 |
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