US3755357A - 2,3 - dihydro - 5-trifluoromethyl-1h-di-benzo(2,3:6,7)thiepino(4,5-c)pyrroles as cns-depressants - Google Patents
2,3 - dihydro - 5-trifluoromethyl-1h-di-benzo(2,3:6,7)thiepino(4,5-c)pyrroles as cns-depressants Download PDFInfo
- Publication number
- US3755357A US3755357A US00145022A US3755357DA US3755357A US 3755357 A US3755357 A US 3755357A US 00145022 A US00145022 A US 00145022A US 3755357D A US3755357D A US 3755357DA US 3755357 A US3755357 A US 3755357A
- Authority
- US
- United States
- Prior art keywords
- acid
- dibenzo
- dihydro
- trifluoromethyl
- thiepino
- 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 - Lifetime
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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
Definitions
- the present invention relates to new thiepin derivatives, to processes for their production, to medicaments containing the new compounds, and to the use thereof.
- R is hydrogen or an unbranched alkyl group having 1-6 carbon atoms or the isopropyl group or the allyl group
- R as an alkyl group having at most 6 carbon atoms is e.g. the methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec.butyl, pentyl, isopentyl or the hexyl group.
- Preferred members of this class are:
- analgesics and anaesthetics, antagonise the action of amphetamine
- mice which had been anaesthetised by intraperitoneal administration of 40 mg./kg. of the short-acting anaesthetic N,N-diethyl-2-methoxy-4-allylphenoxyacetic acid amide potentiates, i.e. prolongs the effect of the anaesthetic to a significant extent.
- methane sulphonate and the hydrochloride salts are preferred, also other pharmaceutically acceptable acid addition salts can be used.
- the pharmacological properties of the compounds of the present invention render them suitable for the treatment of states of tension and agitation.
- reaction product with an inorganic or organic acid, into and addition salt.
- Suitable solvents are such ones which are inert under the reaction conditions, e.g. hydrocarbons such as benzene or toluene, halogenated hydrocarbons such as chloroform, lower alkanols such as methanol or ethanol, ethereal liquids such as ether or dioxane, as well as lower alkanones such as acetone, methyl ethyl ketone, or diethyl ketone.
- hydrocarbons such as benzene or toluene
- halogenated hydrocarbons such as chloroform
- lower alkanols such as methanol or ethanol
- ethereal liquids such as ether or dioxane
- lower alkanones such as acetone, methyl ethyl ketone, or diethyl ketone.
- 10,1l-bis-(bromomethyD-Z-(trifluoromethyl)-dibenzo[b,f]thiepin which corresponds to Formula II, can be produced, for example, by the following process: Starting with [o-(a,a,u-trifluoro-p-tolylthio)- phenyl]-acetic acid [cp. K. Pelz and M. Protiva, Collect. Czechoslov. Chem. Communications 34, 3936 (1969)],
- This acid yields, on reaction with hydrofluoric acid at room'temperature, 11-methyl-8-(trifiuoromethyl)-dibenzo [b,f]thiepin-l(11H)-one, which is reacted with methyl magnesium iodide to obtain 10,1l-dihydro-10,11-dimethyl --8 (trifluoromethyl)-dibenzo [b,t] thiepin-lO-ol.
- a second process, according to the invention for the production of compounds of General Formula I wherein R represents hydrogen comprises hydrolysing a compound of the General Formula IV:
- Ac represents the acyl radical of an organic acid and, if desired, converting the obtained compound into a pharmaceutically acceptable acid addition salt.
- Ac is, in particular, the acyl radical of cyanic acid, of chloroformic acid, of a carbonic acid semi-ester or thiocarbonic acid semi-ester, of a lower alkanecarboxylic acid or of an arenecarboxylic acid.
- acyl radicals Ac are: the cyano, chlorocarbonyl, methoxycarbonyl, ethoxycarbonyl, tert. buto-xycarbonyl, phenoxycarbonyl, benzyloxycarbonyl, methoxythiocarbonyl, methylthio-thiocarbonyl, acetyl, and benzoyl groups.
- hydrolysis of compounds of the General Formula IV is efiected, for example, by several hours heating of such compounds in an alkanolic or aqueous/alkanolic alkali hydroxide solution, e.g. by boiling in a mixture of potassium or sodium hydroxide with ethanol or methanol and a little Water.
- an alkanolic or aqueous/alkanolic alkali hydroxide solution e.g. by boiling in a mixture of potassium or sodium hydroxide with ethanol or methanol and a little Water.
- hydrolysis may be effected, particularly of compounds of the General Formula IV wherein Ac denotes CN, the acyl radical of cyanic acid, also by heating with a mineral acid in an organic/aqueous or aqueous medium, e.g. by several hours boiling in a mixture of 85% phosphoric acid and formic acid
- the starting materials of the GeneralFormula IV are, in their turn, produced, e.g. from compounds of the General Formula I wherein R represents a lower alkyl group, especially the methyl group, or the allyl group; or from 2-benzyl-2,3-dihydro 5 (trifiuoromethyl) 1H dibenzo [2,3 :6,7]thiepino[4,5-c]pyrrole producible analogously to the compounds of the General Formula I, by allowing to act on the stated compounds, at room temperature or at elevated temperature, an organic acyl halide, e.g. a cyanogen halide, particularly cyanogen bromide, also phosgene,
- R represents a lower alkyl group, especially the methyl group, or the allyl group
- 2-benzyl-2,3-dihydro 5 (trifiuoromethyl) 1H dibenzo [2,3 :6,7]thiepino[4,5-c]pyrrole producible analogously to the compounds of
- a chloroformic acid alkyl ester the chloroformic acid phenyl ester or benzyl ester, the chloride or bromide of a lower alkanoic acid or benzoic acid, especially acetyl chloride, acetyl bromide, or benzoyl chloride, whereby occurs, according to the von Braun reaction, the desired acylation with liberation of the alkyl or allyl halide corresponding to the group R, or of a benzyl halide.
- the reaction is carried out'in an inert organic solvent such as, e.g. chloroform or benzene, or, optionally, also in an excess of an acyl halide suitable as reaction medium.
- the compounds of the General Formula I obtained by the process according to the invention are, optionally, subsequently converted, in the usual manner, into their pharmaceutically acceptable acid addition salts.
- an organic solvent is added to a solution of a compound of the General Formula l in' an organic solvent to a solution of a compound of the General Formula l in' an organic solvent is added the acid desired as the salt component, or a solution of the acid.
- organic solvents in which, the formed salt is difficultly soluble, so that it can be separated by filtration.
- solvents are, e.g. methanol, acetone, methyl ethyl ketone, acetone/ethanol, methanol/ ether, or ethanol/ether.
- salts for use asmedicaments it is possible to use, instead of free bases, pharmaceutically acceptable acid addition salts, i.e. salts with such acids of which the anions are not toxic in the case of the dosages in question. Furthermore, it is of advantage if the salts to be used as medicaments crystallise well and are not, or only slightly, hygroscopic. For salt formation with compounds of the General Formula I it is possible to use, e.g.
- hydrochloric acid hydrobromic acid, sulphuric acid, phosphoric acid, methanesulphonic acid, ethanesulphonic acid, B-hydroxyethanesulfonic acid, acetic acid, malic acid, tartaric acid, citric acid, lactic acid, oxalic acid, succinic acid, fumaric acid, maleic acid, benzoic acid, salicyclic acid, phenylacetic acid, mandelic acid and embonic acid.
- the new active substances are administered orally, rectally, or parenterally.
- the dosage depends on the manner of administration, the species, the age, and on the individual condition.
- the daily dosages of the free bases or of pharmaceutically acceptable salts thereof vary between 0.1 mg./kg. and 10 rag/kg. for warm-blooded animals.
- Suitable dosage units, such as drages, tablets, suppositories or ampoules, preferably contain 2100 mg. of an active substance according to the invention.
- Dosage units for oral administration preferably contain as active substance between 1 and 90% of a compound of the General Formula I, or of a pharmaceutically acceptable salt of such a compound. They are produced by combining the active substance, e.g. with solid pulverulent carriers such as lactose, saccharose, sorbitol, mannitol; starches such as potato starch, maize starch or amylopectin, also laminaria powder or citrus pulp powder; cellulose derivatives of gelatine, optional with the addition of lubricants such as magnesium or calcium stearate, or polyethylene glycols, to form tablets or drage cores.
- solid pulverulent carriers such as lactose, saccharose, sorbitol, mannitol
- starches such as potato starch, maize starch or amylopectin, also laminaria powder or citrus pulp powder
- cellulose derivatives of gelatine optional with the addition of lubricants such as magnesium or calcium stearate, or polyethylene glyco
- ' drage cores are coated, e.g. with conc. sugar solutions which may also contain, e.g. gum arabic, talcum and/or titanium dioxide; or they are coated with a lacquer dissolved in readily volatile organic solvents or mixtures of solvents. Dyestuits may be added to these coatings, e.g. for identification of the varying dosages of active sub stance.
- conc. sugar solutions which may also contain, e.g. gum arabic, talcum and/or titanium dioxide; or they are coated with a lacquer dissolved in readily volatile organic solvents or mixtures of solvents.
- Dyestuits may be added to these coatings, e.g. for identification of the varying dosages of active sub stance.
- Further dosage units suitable for oral administration are hard gelatine capsules, as well as soft closed capsules made from gelatine and a softener such as glycerin.
- the hard capsules contain the active substance preferably as a. granulate, e.g. in admixture with fillers such as maize starch, and/or lubricants such as talcum or magnesium stearate, and, optionally, stabilisers such as sodium metabisulphite (Na S O or ascorbic acid.
- the active substance is preferably dissolved or suspended in suitable liquids such as liquid polyethylene glycols, whereby likewise stabilisers may be added.
- Suitable dosage units for rectal administration are, eg. suppositories consisting of a combination of an act ve substance with a fatty base. Also suitable are gelatme rectal capsules containing a combination of the active substance with polyethylene glycol.
- Ampoules for parenteral administration especially ntramuscular administration, preferably contain as active substance a water-soluble salt in a concentration of preferably 0.5-5 optionally together with suitable stabilisers and buffer substances, in aqueous soltuion.
- a granulate is produced from 100 g. of 2-ethyl- 2,3 dihydro 5 (trifluoromethyl)-lH-dibenzo[3,4:6,7] thiepino[4,5-c]pyrrole methane sulphonate, 175.90 g. of lactose, and the alcoholic solution of 10 g. of stearic acid; after drying, the granulate is mixed with 56.60 g. of colloidal silicon dioxide, 165 g. of talcum, 20 g. of potato starch, and 2.50 g. of magnesium stearate; and the mixture is then pressed to form 10,000 drage cores. These are subsequently coated with a concentrated syrup made from 502.28 g.
- a suppository foundation substance is prepared from 2.5 g. of 2-ethyl-2,3-dihydro 5-(trifiuoromethyD- 1H dibenzo[3,4:6,7]thiepino[4,5-c]pyrrolemethane sulphonate and 167.5 g. of adeps solidns; it is then used to fill 100 suppositories each containing 25 mg. of active substance.
- Example 1 An amount of 23.2 g. (0.05 mol) of 10,11-bisbromomethyl -2- (trifiuoromethyl -dibenzo [b,f] thiepin is dissolved in ml. of abs. benzene. This solution is added dropwise at 40, within one hour, to a solution of 40 g. (ca. 0.9 mol) of ethylamine in 200 ml. of methanol. The reaction mixture is stirred for a further 2 hours at 50, and the solvent and excess ethylamine are subsequently distilled off. To the residue are added 100 ml. of water, and the obtained suspension is extracted with ether.
- the 10,11-bis-(bromomethyl) 2 (trifluoromethyl)- dibenzo[b,f]thiepin required as starting material is produced as follows:
- the ethanol is to a great extent then evaporated off in vacuo and the residue extracted by shaking with ether and water.
- the etheral phases are washed with Water until neutral, dried over magnesium sulphate, and the solvent is evaporated oil? in vacuo.
- the obtained oily residue is distilled in high vacuum.
- the succinimide is filtered off, washed out with carbon tetrachloride, and the filtrate extracted by being shaken with dilute sodium bicarbonate solutions.
- the organic phases are thereupon Washed with water until neutral, dried over magnesium sulphate, and the solvent is evaporated off in vacuo.
- the residue is recrystallised from ether/petroleum ether.
- Example 2 (a) 3.9 g. (0.01 mol) of crude 2-ethoxycarbonyl-2,3- dihydro 5 (trifiuoromethyl) 1H-dibenzo[2,3:6,7]- thiepino[4,5-c]pyrrole are refluxed with a mixture of 7 ml. of 48% aqueous hydrobromic acid and 21 ml. of acetic acid for 4 hours followed by evaporating the reaction mixture. The residue is dissolved in ml. of water and the solution obtained is rendered alkaline with conc.sodium hydroxide solution followed by extracting with an ether/methylenechloride solution (2:1).
- the organic layer is extracted with three portions of each 20 ml. of an 1-n aqueous methane sulphonic acid solution, the combined acid axtracts are rendered alkaline with conc.sodium hydroxide solution and the whole mixture is extracted with an ether/methylenechloride solution (2:1).
- the organic layer is washed with water, dried over magnesium sulphate and evaporated to dryness in vacuo.
- the crude base obtained is dissolved in acetone and converted to the hydrochloride by reacting with an ethereal hydrochloric acid solution.
- a compound of the Formula I R is hydrogen or an unbranched alkyl group having 1-6 carbon atoms, the isopropyl group or the allyl group, and the pharmaceutically acceptable acid addition salts thereof.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH779870A CH531535A (de) | 1970-05-26 | 1970-05-26 | Verfahren zur Herstellung von neuen Thiepinderivaten |
Publications (1)
Publication Number | Publication Date |
---|---|
US3755357A true US3755357A (en) | 1973-08-28 |
Family
ID=4330648
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US00145022A Expired - Lifetime US3755357A (en) | 1970-05-26 | 1971-05-19 | 2,3 - dihydro - 5-trifluoromethyl-1h-di-benzo(2,3:6,7)thiepino(4,5-c)pyrroles as cns-depressants |
Country Status (21)
Country | Link |
---|---|
US (1) | US3755357A (no) |
JP (1) | JPS5411320B1 (no) |
AT (2) | AT307423B (no) |
BE (1) | BE767702A (no) |
CA (1) | CA939354A (no) |
CH (1) | CH531535A (no) |
CS (1) | CS172926B2 (no) |
DE (1) | DE2125892C3 (no) |
DK (1) | DK127431B (no) |
ES (1) | ES391524A1 (no) |
FI (1) | FI50983C (no) |
FR (1) | FR2100684B1 (no) |
GB (1) | GB1334945A (no) |
IE (1) | IE35251B1 (no) |
IL (1) | IL36917A (no) |
NL (1) | NL7106926A (no) |
NO (1) | NO132355C (no) |
PL (1) | PL81553B1 (no) |
SE (1) | SE358396B (no) |
SU (1) | SU389663A3 (no) |
ZA (1) | ZA713370B (no) |
Cited By (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 |
US4045570A (en) * | 1974-05-10 | 1977-08-30 | Ciba-Geigy Corporation | Heterocyclic S-imino-S-oxides |
US4263315A (en) * | 1978-07-07 | 1981-04-21 | Ciba-Geigy Corporation | Azatetracyclic carbonitriles |
US4492691A (en) * | 1979-12-10 | 1985-01-08 | Ciba-Geigy Corporation | Azatetracyclic carbonitriles |
-
1970
- 1970-05-26 CH CH779870A patent/CH531535A/de not_active IP Right Cessation
-
1971
- 1971-05-19 NL NL7106926A patent/NL7106926A/xx not_active Application Discontinuation
- 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 DK DK242071AA patent/DK127431B/da unknown
- 1971-05-19 SE SE06522/71A patent/SE358396B/xx unknown
- 1971-05-19 FI FI711383A patent/FI50983C/fi active
- 1971-05-24 SU SU1663201A patent/SU389663A3/ru active
- 1971-05-24 CS CS3783A patent/CS172926B2/cs unknown
- 1971-05-25 ES ES391524A patent/ES391524A1/es not_active Expired
- 1971-05-25 PL PL1971148351A patent/PL81553B1/pl unknown
- 1971-05-25 IL IL36917A patent/IL36917A/xx unknown
- 1971-05-25 AT AT449971A patent/AT307423B/de not_active IP Right Cessation
- 1971-05-25 DE DE2125892A patent/DE2125892C3/de not_active Expired
- 1971-05-25 CA CA113,749A patent/CA939354A/en not_active Expired
- 1971-05-25 IE IE660/71A patent/IE35251B1/xx unknown
- 1971-05-25 AT AT499972A patent/AT307429B/de not_active IP Right Cessation
- 1971-05-25 JP JP3528971A patent/JPS5411320B1/ja active Pending
- 1971-05-25 ZA ZA713370A patent/ZA713370B/xx 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/xx unknown
Cited By (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 |
US4045570A (en) * | 1974-05-10 | 1977-08-30 | Ciba-Geigy Corporation | Heterocyclic S-imino-S-oxides |
US4263315A (en) * | 1978-07-07 | 1981-04-21 | Ciba-Geigy Corporation | Azatetracyclic carbonitriles |
US4492691A (en) * | 1979-12-10 | 1985-01-08 | Ciba-Geigy Corporation | Azatetracyclic carbonitriles |
Also Published As
Publication number | Publication date |
---|---|
CA939354A (en) | 1974-01-01 |
FI50983B (no) | 1976-05-31 |
FI50983C (fi) | 1976-09-10 |
BE767702A (fr) | 1971-11-26 |
NL7106926A (no) | 1971-11-30 |
ZA713370B (en) | 1972-01-26 |
ES391524A1 (es) | 1973-06-16 |
DE2125892C3 (de) | 1980-07-03 |
PL81553B1 (no) | 1975-08-30 |
IL36917A0 (en) | 1971-07-28 |
AT307423B (de) | 1973-05-25 |
CS172926B2 (no) | 1977-01-28 |
CH531535A (de) | 1972-12-15 |
NO132355C (no) | 1975-10-29 |
DE2125892B2 (de) | 1979-10-18 |
AT307429B (de) | 1973-05-25 |
NO132355B (no) | 1975-07-21 |
IL36917A (en) | 1974-03-14 |
FR2100684B1 (no) | 1975-10-10 |
DK127431B (da) | 1973-11-05 |
IE35251B1 (en) | 1975-12-24 |
FR2100684A1 (no) | 1972-03-24 |
GB1334945A (en) | 1973-10-24 |
IE35251L (en) | 1971-11-25 |
SE358396B (no) | 1973-07-30 |
JPS5411320B1 (no) | 1979-05-14 |
SU389663A3 (no) | 1973-07-05 |
DE2125892A1 (de) | 1971-12-09 |
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