IL34689A - 1h-2,3,4,5-tetrahydro-1,5-benzodiazepin-4-ones,their preparation and pharmaceutical compositions containing them - Google Patents

1h-2,3,4,5-tetrahydro-1,5-benzodiazepin-4-ones,their preparation and pharmaceutical compositions containing them

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Publication number
IL34689A
IL34689A IL34689A IL3468970A IL34689A IL 34689 A IL34689 A IL 34689A IL 34689 A IL34689 A IL 34689A IL 3468970 A IL3468970 A IL 3468970A IL 34689 A IL34689 A IL 34689A
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IL
Israel
Prior art keywords
formula
compound
group
effected
reaction
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Application number
IL34689A
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Hebrew (he)
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IL34689A0 (en
Original Assignee
Boehringer Sohn Ingelheim
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority claimed from DE19691929656 external-priority patent/DE1929656A1/en
Priority claimed from DE19702006600 external-priority patent/DE2006600A1/en
Priority claimed from DE19702019627 external-priority patent/DE2019627A1/en
Application filed by Boehringer Sohn Ingelheim filed Critical Boehringer Sohn Ingelheim
Publication of IL34689A0 publication Critical patent/IL34689A0/en
Publication of IL34689A publication Critical patent/IL34689A/en

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Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D243/00Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
    • C07D243/06Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
    • C07D243/10Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
    • C07D243/121,5-Benzodiazepines; Hydrogenated 1,5-benzodiazepines

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Plural Heterocyclic Compounds (AREA)

Description

their preparation compositions containing them 32826 This invention relates to tetrahydrobenzodiazepinones having interesting physiological activities and processes for the preparation According to one feature of the invention there are compounds of the general formula wherein ia an acyclic hydrocarbyl group to 6 carbon atoma an group of 2 or 3 carbon a oyoloalkylraethyl group in which the cycloalkyl j group contains from 3 to 6 carbon or a formyl is group optionally substituted in the with nitro or nitro or cyano provided that may have additionally the meaning of chlorine is hydroxyalkyl of 2 or 3 carbon atoms or or R2 is or phenyl with nitro or j and physiologically acceptable acid addition salts of i oorapounde of formula I which are capable of forming such i The compounds according to the invention exhibit esting physiological activities and in particular an esting tranquillizing Particularly preferred compounds of formula I by virtue of this interesting activity hexyl or cyelopropylmethyl R2 represents a phenyl group substituted by a chlorine or bromine atom in the and represents a chlorine or bromine The compounds according to the invention which are preferred by virtue of their especially interesting physiological activities include 1 2 4 7 and physiologically compatible acid addition salts and and The compounds of formula I may be for by one of the following processes compounds wherein represents other than a arylation or heteroarylation of a benzodiazepine is as hereinbefore defined for with the with an halide or an of formula is as hereinbefore defined and X represents a halogen The reaction for be effected in the presence of copper and an alkali metal if desired at an elevated temperature and conveniently in an It is preferred to add a a weak organic base such as pyridine a such as which does not react with the reactantsJ the preparation of compounds wherein represents other than a formyl cyclization of a substituted phenylenediamine of formula and are as hereinbefore The compounds of formula IV may be for by activating the carboxyl group thereof in a conventional manner The page 76 Academic and to form a reactive derivative of the compound of formula Suitable reactive derivatives for the corresponding acid chlorides or mixed acid anhydrides for example oh heating if in the presence ofa basic condensation may be converted into the desired benzodiazepinone compounds wherein represents other than a formyl cyclization of an of formula and are as hereinbefore defined and Y represents a vinyl or a The compounds of formula V may conveniently be cyclised in the presence of an organic or inorganic or in the presence of a catalytic quantity of an acidic compound such as a dilute mineral or If the reaction may be effected in the presence of a preferably a lower a lower carboxylic acid or The reaction is advantageously effected under increased pressure conveniently in an autoclave or under reflux in compounds wherein represents other than a hydrogen of a compound of formula and are as hereinbefore with alkylating agent of formula is as hereinbefore defined for with the 5 1 exception of a hydrogen atom and Y represents a group readily removable as an anion a halogen atom or a sulphonyl if desired in the presence of a basic condensation agent such as sodamide or a sodium alkoxide sodium If represents a hydroxyalkyl the alkylation of compounds of formula VI is preferably effected using a alcohol advantageously in the presence of a weak organic or organic The reaction is preferably effected at an elevated temperature and where necessary in an Under certain circumstances the reaction may with advantage be effected in an organic solvent such as a lower or higher alcohol Compounds of formula I containing a group in the may be for by reacting a compound of formula VI with ethylene for example in the presence of a strong Triton B ammonium The reaction if be effected in a solvent or a mixture of solvents such as an dimethylformamide if in mixture with If represents a formyl group in the desired compound of formula the reaction may conveniently be effected by heating a compound of formula VI in formic Some of the starting materials required for processes to are known and they may be prepared by one of the processes described The compounds of formula II may be for from compounds of formula and are as hereinbefore for by reducing the nitro group thereof with a reducing agent such as In the diazepine ring closes spontaneously upon reduction of the nitro When using other reducting cyclization may subsequently be if in a manner corresponding to that described above at Compounds of formula wherein represents a nitro may be selectively reduced using ammonium Compounds of formula VIII if be prepared by the addition of acrylic acid to the correspondingly stituted Compounds of formula IV may be for from the corresponding or of iormula and are as hereinbefore by the addition of acrylic acid to the amino group of the compound obtained by reduction of the nitro group of the compound of formula by the acylation of the correspondingly substituted and protected compounds of formula and are as hereinbefore defined and Sch represents a hydrolytically removable group except when represents a nitro a hydrogenolytically removable such as a acyl or carboxyalkyl and subsequent removal of the protecting For the preparation of the starting materials of formula which are required for process the processes described under to above may be used and these lead to compounds of formula I wherein represents a hydrogen Compounds of formula except those wherein represents a formyl group and represents other than an group if be converted into acid addition salts thereof due to their Suitable acids for the preparation of such salts for hydrohalic hydrochloric sulphuric acid and sulphonic The conversion into such salts may be effected in a conventional manner and when two basic nitrogen atoms are for example when represents other than a formyl group and represents an diacid addition salts may be According to a yet further feature of the invention there are provided pharmaceutical compositions comprising as active ingredient at least one compound according to the invention as hereinbefore defined association with a pharmaceutical carrier or The compositions according to the invention may if desired also contain one or more further physiologically active When a further physiologically active substance is used it for be a spasmolytic or active Suitable forms of administration for emulsions or dispersible The corresponding tablets for be prepared by mixing the active ingredient or active ingredients for known with inert such as calcium carbonate or calcium disintegrants such as corn starch or alginic starch or lubricants such as magnesium stearate or talc agents for obtaining a sustained release effect such as carboxypolymethylene acetatephthalate or polyvinylacetate The tablets if be formed from several for may be produced for example by coating cores produced analogously to tablets and for the agents conventionally used for tablet coatings such as gum titanium dioxide or For obtaining a sustained release effect or for avoiding the core may also be in the form of several The tablet coat if also be prepared from several layers so as to provide a sustained release coating tablets may be Syrups of the active ingredients or active ingredient combinations if also contain a sweetening agent such as glycerin or as well as an agent for improving the taste of the for flavours such as vanillin or The syrups if include suspending agents or thickeners such as sodium carboxymethylcellulose wetting agents such as the condensation products of fatty alcohols with ethylene oxide preservatives such as benzoates Injection solutions for be produced in conventional for example with the addition of ervatives such as or stabilizers such as alkali metal salts of ethylenediaminetetraacetic acid and then used to fill injection vials or Capsules containing one or more active ingredients or active ingredient combinations for be produced by mixing the active ingredients with inert carriers such as lactose or sorbitol and using the mixture to fill gelatin capsules Suitable suppositories may be for by mixing the active ingredient with a suppository base such as a neutral fat or polyethylene glycol or derivatives The compositions according to the invention are veniently administered in dosage unit Such dosage units preferably contain from to mg of active ingredient according to the invention and advantageously according to the invention is ageously from to mg per The following examples are given by way illustration Example 1 to process 6 g of are dissolved in 20 ml of dry dimethylformamide and ml of absolute tetrahydrofuran and mixed g of The solution is stirred at room temperature for 1 12 g of crotyl bromide are added and the mixture is allowed to react for 2 hours at room then for 3 hours at The reaction mixture is further processed with neutralized with glacial acetic acid and evaporated The residue is mixed with ml of water and extracted into methylene The oily is i I i o as The product is crystallized from ί r py o l g 2 benzodiaz 10 g of are n 500 and 50 ml of and mixed with 75 ml of ethylene oxide and ml of Triton B After heating for 90 hours at the reaction mixture is evaporated rn vacuo and the residue is crystallized from g 15 1 by b I l 10 g are reacted with ethylene as described in Example Unreacted starting material and l t ed by s column chromatography ethyl The product crystallizes after trituration with g Example 1 6 g of 4 are heated with 6 g of potassium of potassium iodide and 30 ml of for 6 hours in an autoclave at Subsequently the mixture is evaporated vacuo taken up in methylene chloride and extracted with After drying the extract with magnesium it is evaporated in vacuo and the products are separated by silicagel column chromatography as in Example 1 2 g 15 Example A mixture of 6 g of 4 ml of bromobenzene 20 ml of diethylenediglycoldimethyl 6 g of potassium 1 g of chloride and g of oxide are refluxed with vigorous stirring for 3 After pletion of the reaction charcoal is and the mixture is filtered with suction through hot kieselguhr0 The filtrate is washed with methylene evaporated in vacuo and the residue is recrystallized from 3 g 51 153 6 Example 3 are refluxed for 3 hours in ml Subsequently the solution is diluted with neutralized with ammonia and extracted with methylene After drying the extract with magnesium the solution is evaporated and crystallized from g 158 In accordance with the method of the above the following compounds were Example i 7 H CI 171 72 8 H 152 53 9 H 134 10 H 150 1 11 H 1 H 13 H 232 33 14 H 33 15 H 233 35 16 170 CH C6H5 17 C6H5 144 45 N02 160 62 19 N02 126 27 Example C 168 23 N02 26 24 45 123 C6H5 26 91 92 27 H CI 159 60 28 H CI 186 88 t H CN 175 80 30 H OH I9 93 31 Oil 32 114 15 33 Oil 34 Br 122 24 35 Br 141 42 36 Br 31 Br 144 45 38 Br 123 24 88 89 176 78 41 H Br 183 85 42 Br 158 60 Br 129 30 i Example R NO J Example Coated Tablets 1 tablet core comprises tetra lactose corn starch gelatin magnesium stearate lactose corn starch gelatin magnesium stearate lactose corn starch gelatin magnesium stearate ose mg corn mg gelatin magnesium stearate mg mg lactose corn starch mg gelatin magnesium stearate mg rag rag lactose corn starch mg gelatin mg magnesium stearate mg mg A mixture of the active corn starch and lactose is granulated through mesh screen using a aqueous gelatin The granulate is dried pressed once more through a The granulate obtained is mixed with magnesium stearate and pressed to cores which are coated with a shell in the conventional The shell consists of an aqueous suspension of titanium talc and gum The finished tablets are polished with Final weight of coated 100 Example Suppositories 1 suppository rag suppository base a triglyceride mg Prepar The finely is into the molten wi th aid of an immersion The poured into slightly precooled moulds at 20 insufficientOCRQuality

Claims (1)

1. CLAIMS 1. •Benzodiazepine compounds of the formula wherein 1 is hydrogen, an acyclic hydrocarbyl group of 1 to 6 carbon atoms , an O-hydroxyalkyl group of 2 or 3 carbon atoms, a cycloalkylraethyl group In which the cycloalkyl group contains from 3 to 6 carbon atoms, or a formyl group; R2 is oc-pyridyl,/ phenyl group optionally substituted in the o-position with halogen, nitro or trifluoromethyl; R~ is or a bromine ,/ hydroxy , trifluoromethyl, nitro or cyano group; provided that -j may have additionally the meaning of chlorine if: (a) R, is ut- hydroxyalkyl of 2 or 3 carbon atoms or formyl, or (b) R is ct-pyridyl or phenyl o-substituted with fluoro, bromo, nitro or trifluoromethyl; and physiologically acceptable acid addition salts of these compounds of formula I which are capable of forming such salts. 2. 7-Nitro-5-phenyl-lH-2 ,3,4, 5-tetrahydro-1 , 5-benzo-diazepine-4-one . 3* l-Allyl-7-nitro-5-phenyl-lH-2,3,4,5-tetrahydro-l,5-benzodiazepine-4-one . 4. 7-Nitro-5-( 2-chlorophenyl)-H-2 ,3,4,5-tetrahydro-1, 5-benzodiazepine-4-one . 34689/2 2' 21 5. 1- ( -ButenylV7-nitro-5-phenyl-lH-2>3,4,5-tetrahydro- , 1 ,5-benzodiazepin-4-one» 6* Physiologicall acceptable salts of the compounds according to any one of Claims 2 to 6, e.g. hydrohalides , sulfates or methanesulfo ates. 7. 1-Formyl-5-phenyl-7-trifluoromethy1-1H-2, 3,4,5-tetrahydro-1, 5-benzodiazepin-4-one. 8· l-Formyl-5-phenyl-7-nitro-lH-2,3,4,5-tetrahydro-1 ,5-benzodiazepin-4-one . 9#„ Compounds as claimed in Claim' 1, as herein specifically listed. . ■ · . lO , A process for the preparation of compounds of formula I in Claim 1, with the exception of those wherein R^ is a formyl , group, which comprises reacting a compound of formula. wherein R2 and R,3 are as defined in Claim 1 and R. is as 4 defined for R^ in Claim 1 with the exception of a formyl group, with an arylating or heteroarylating agent of formula 2 (III) where Rg is as defined in Claim 1 and X is halogen, and, if desired, converting the compound of formula I produced into a physiologically acceptable acid addition salt thereof. . Is' 11. A process as claimed in Claim 10-, wherein the reaction is effected in the presence of copper and an alkali metal acetate. .12. A process as claimed in Claims 1 lO or ,11 , wherein the reaction is effected at an elevated temperature. ^ 34689/2 - .2 - 22 13» A process as claimed in Claim 10, wherein the reaction is effected in the presence of a copper(I) salt, CuO, a weak organic base* e.g. pyridine, and/or a solvent which does not react with the reactants, e.g. xylene. 14. A process for the preparation of compounds of formula I in Claim 1, with the exception of those in which is a formyl group, which comprises cyclising a compound of formula where Rg and R^ are as defined in Claim 1 and R^ is as defined in Claim 10, and, if desired, converting the compound of formula' I produced into a physiologically acceptable acid addition salt thereof. 15. A process as claimed in Claim 14, wherein the carboxyl group of the compound of formula IV is activated prior to cyclisation, e.g., by converting the carboxyl group into a ester, an acid chloride or a mixed anhydride thereof. 16· -A process as claimed in Claims 14 or 15, wherein the reaction is effected at an elevated temperature. 17· A process as claimed in any of Claims .1 to l6' , wherein the reaction is effected inlhe presence Qf a basic condensation agent . ! 18· . A process for the preparation of compounds of formula I in Claim 1, with the exception of those in which - is a formyl group, which comprises cyclising a compound of formula ft> ,. ..34689/2 23 s ' . where R2 and R-j are as defined in Claim 1, ^ is as defined .in Claim 11 and Y is a vinyl or a 2-haloethyl group and, if desired, converting the compound of formula I produced into a physiologically acceptable acid addition salt thereof. 19. A process as claimed in Claim 18', wherein the cyclisation is effected in the presence of a base. 20. A process as claimed to Claim 18, wherein the cyclisation is effected in the presence of a catalytic quantity of an acidic compound, e.g., a dilute mineral acid, £-toluenesulphonic acid, AlCl^ or. Z Clg* 21· A process as claimed in any of Claims 18 to 20, wherein the reaction is effected in a solvent, e.g. , a lower alcohol, a lower carboxylic acid or ■ etrahydrofuran. 22· A process as claimed in any of Claims 18 to 21, wherein the reaction is effected under euperatmospheric pressure. , 23· A process for the preparation of compounds of formula I in Claim 1, with the exception of those in which is hydrogen, wherein a compound of formula a compound of formul Rc where R-. is as defined in Claim 1 for R, with the exception of hydrogen, and Y is a group readily removable as an anion, and the compound of formula I produced is, if desired, converted into an acid addition salt thereof. 24. A process as claimed in Claim 23, wherein Y in the compound of formula VII is halogen or a toluenesulfonyl group. 25. A process as claimed in Claims 2-3 or 24, wherein the reaction is effected in the presence of a basic condensation agent, e.g. , sodamide or a sodium alkoxide. 26 i A process as claimed in Claims 23 or 24, wherein the compound of formula VII is a halo-alcohol and the reaction is effected in the presence of a weak organic or inorganic base · 27. A process as claimed in any of Claims .23 to 26,5lwherein the reaction is effected at an elevated temperature. 28. A process as claimed in any of Claims 23 to 27 , wherein the reaction is effected in an organic solvent, e.g., an alcohol. 29. A process for the preparation of compounds of formula I in Claim 1, in which is a 2-hydroxyethyl group, wherein a compound of formula VI in Claim ,23 is reacted with ethylene oxide and the compound of formula I produced is, if desired, converted into a physiologically acceptable acid addition salt thereof. 30. A process as claimed in Claim 29, wherein the reaction is effected in the presence of a strong base, e.g., trimethylbenzylammonium hydroxide. 54689/2 - ,27 - 25 31. A process as claimed in Claims 29 or 50, wherein the reaction is effected in a solvent or a mixture of solvents, e.g.,. an alcohol, tetrahydrofuran, dimethylformamide or mixtures thereof and, if desired, water. 32. A process for the preparation of compounds of formula I in Claim 1 in which R1 is a formyl group, wherein a compound of formula VI in Claim 2J is reacted with formic) acid and the compound of formula I produced, in case is an a-pyridyl group, is, if desired, converted into a physiologically acceptable acid addition salt thereof. 33. Processes for the preparation of compounds of formula I in Claim 1 , substantially as herein described with reference to the Examples. 34. Pharmaceutical compositions comprising as active ingredient at least one compound of formula I in Claim 1. . 35. Compositions as claimed in Claim 34 which contain a spasmolytic or a psychopharmacologically active agent as a further active ingredient. 36. Compositions as claimed in Claims 3 or 35 in the form of tablets, capsules, suppositories, solutions, juices, emulsions or dispersible powders. 37* Compositions as claimed in any of Claims 3 to 36 in the form of dosage units. 38. Compositions a3 claimed in Claim ^ , wherein each dosage unit contains from 0.5 to 50 mg, e.g., from 1 to 25 mg, of a compound of formula I in Claim 1. 39. Pharmaceutical compositions as claimed in any of Claims 34 to 38 , substantially as herein described with reference to the Examples.
IL34689A 1969-06-11 1970-06-09 1h-2,3,4,5-tetrahydro-1,5-benzodiazepin-4-ones,their preparation and pharmaceutical compositions containing them IL34689A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19691929656 DE1929656A1 (en) 1969-06-11 1969-06-11 Tetrahydro-1,5-benzodiazepine-4-ones
DE19702006600 DE2006600A1 (en) 1970-02-13 1970-02-13 Tetrahydro-1,5-benzodiazepine-4-ones
DE19702019627 DE2019627A1 (en) 1969-06-11 1970-04-23 Tetrahydro-1,5-benzodiazepine-4-ones

Publications (2)

Publication Number Publication Date
IL34689A0 IL34689A0 (en) 1970-08-19
IL34689A true IL34689A (en) 1973-03-30

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Application Number Title Priority Date Filing Date
IL34689A IL34689A (en) 1969-06-11 1970-06-09 1h-2,3,4,5-tetrahydro-1,5-benzodiazepin-4-ones,their preparation and pharmaceutical compositions containing them

Country Status (16)

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JP (3) JPS5013273B1 (en)
AT (2) AT303737B (en)
BE (1) BE751834A (en)
BG (4) BG17602A3 (en)
CA (1) CA967154A (en)
CH (1) CH549582A (en)
ES (4) ES380557A1 (en)
FR (1) FR2052950B1 (en)
GB (1) GB1317475A (en)
IE (1) IE35727B1 (en)
IL (1) IL34689A (en)
NL (1) NL7008404A (en)
NO (1) NO129524B (en)
RO (4) RO58405A (en)
SE (1) SE381873B (en)
SU (1) SU423299A3 (en)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110256365B (en) * 2019-06-24 2022-06-07 陕西师范大学 Method for preparing benzodiazepine derivative by catalysis of dichlorotitanocene
CN110183397B (en) * 2019-06-24 2022-08-23 陕西师范大学 Method for preparing 1, 5-benzothiazine compound by catalysis of zirconocene dichloride

Also Published As

Publication number Publication date
SU423299A3 (en) 1974-04-05
CH549582A (en) 1974-05-31
CA967154A (en) 1975-05-06
NO129524B (en) 1974-04-22
IE35727L (en) 1970-12-11
RO58641A (en) 1975-09-15
FR2052950B1 (en) 1974-08-30
ES387136A1 (en) 1974-01-01
JPS5013273B1 (en) 1975-05-19
GB1317475A (en) 1973-05-16
JPS5031158B1 (en) 1975-10-07
BG17603A3 (en) 1973-11-10
SE381873B (en) 1975-12-22
RO58640A (en) 1975-10-15
AT303737B (en) 1972-12-11
ES380557A1 (en) 1973-04-01
BG17974A3 (en) 1974-03-05
BE751834A (en) 1970-12-11
IE35727B1 (en) 1976-05-12
RO58887A (en) 1975-10-15
BG17973A3 (en) 1974-03-05
AT303746B (en) 1972-11-15
IL34689A0 (en) 1970-08-19
NL7008404A (en) 1970-12-15
FR2052950A1 (en) 1971-04-16
ES387137A1 (en) 1974-01-01
ES387138A1 (en) 1973-05-01
JPS49192B1 (en) 1974-01-05
RO58405A (en) 1975-11-15
BG17602A3 (en) 1973-11-10

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