US3892695A - Pyrimidino-dibenzo-azepine,-oxazepine,-thiazepine and diazepine derivatives - Google Patents

Pyrimidino-dibenzo-azepine,-oxazepine,-thiazepine and diazepine derivatives Download PDF

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US3892695A
US3892695A US396251A US39625173A US3892695A US 3892695 A US3892695 A US 3892695A US 396251 A US396251 A US 396251A US 39625173 A US39625173 A US 39625173A US 3892695 A US3892695 A US 3892695A
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dibenzo
azepine
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pyrimidino
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Der Burg Willem Jacob Van
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Akzona Inc
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    • 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
    • A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
    • A61K31/551—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having two nitrogen atoms, e.g. dilazep
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—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
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
    • A61K31/553—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having at least one nitrogen and one oxygen as ring hetero atoms, e.g. loxapine, staurosporine
    • 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
    • A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
    • A61K31/554—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having at least one nitrogen and one sulfur as ring hetero atoms, e.g. clothiapine, diltiazem
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/20—Hypnotics; Sedatives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/24—Antidepressants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/26—Psychostimulants, e.g. nicotine, cocaine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D498/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
    • C07D513/04—Ortho-condensed systems

Definitions

  • OXAZEPlNE,-THIAZEPINE AND DIAZEPINE DERIVATIVES [75] Inventor: Willem Jacob van der Burg, Heesch,
  • the present invention relates to novel biologically active pyrimidino derivatives. More particularly it relates to heXahydro-pyrimidino-dibenzo-azepines and 5 r A 1 7 tetrahydro-pyrimidino-dibenzo-oxazepines, -thiazepines and -diazepines. It a From the British Pat. No. l.229.252 compounds are known differing from the present compounds in that they contain a piperazine instead of a pyrimidino ring. in which These known piperazine derivatives possess potent an- Y represents hydrogen 2 Oxygen or Sulphur and tihistamine and antiserotonine activity.
  • R and R- represent hydroxy. halogen. alkyl or alkoxy with 1-6 carbon atoms. acyloxy with 1-8 carbon atoms. or a trifluoromethyl group,
  • R hydrogen, an alkyl group with 1-6 carbon atoms.
  • the groups 2 and 2 may represent halogen. a substituted or unsubstituted amino group. a free. etherified or esterified hydroxy or mercapto group or group Z and Z together may represent sulphur or oxygen.
  • X i sulphgir the guoup or the group If Y represents hydrogen H), Z and Z stand preferabl for halogen or hydroxy groups.
  • Reagents III hydrogen or u lower "ukyl group F6 belonging to this type of compounds are. for example. Carbon moms methylenechloride. methylenebromide or methylene as well as the pharmaceutically acceptable acid addidiol formaldehyde Solution in water or a Water Com tion salts and pharmaceutically acceptable quaternary mining solvent).
  • ammonium compouljds thereof have a completely If Y represents oxygen or sulphur the most suitable ferem pharmacological profile
  • the compounds 4O moieties for Z, and Z are halogen. substituted or ancording to this invention snow. fully contrary to the substituted amino groups, an etherified or compounds described in the said British patent. a posiphonylated hydroxy or mercapto group or Z1 and Z2 tive effect in the reserpine antagonism test. which together are sulphur (in combination with Y sulmeans that h uml-qepressanf t F phur).
  • Suitable reagents lll belonging to this type of whereas the antihistamine and antl-serotonme activity compounds are for example phosgene, thiophosgene the P compounds cnflsfderaply lowered in haloformic esters such as ethylchloroformate. esters of comparison Tong antihistamine Q carbonic acid such as dimethylor diethylcarbonate. tiserotonine activity of the compounds descrlbed in the urea and urea derivatives such as thiourea or N'- British P bonyl-di-imidazole. and carbondisulphide.
  • the Compwnds according to'the invention Q be Preferably methylenehalide or formaldehyde (in wa- P p y y method Commonly used for this type ter) is used as the reagent Ill in the present condensahf P y however P p most tion reaction if the starting compound II does not conveniently starting from a substance with the general mi a k m group (Q H because they yield the formula: sired final product according to the invention in a direct way.
  • methylenehalide or formaldehyde in wa- P p y y method Commonly used for this type ter
  • P p most tion reaction if the starting compound II does not conveniently starting from a substance with the general mi a k m group (Q H because they yield the formula: sired final product according to the invention in a direct way.
  • any suitable reducing agent can be used.
  • metal hydrides such as sodium hydride. lithium aluminium hydride or diborane.
  • Said reduction can also be or an acid addition salt thereof. in which preformed catalytically by hydrogenation in the pres- X.
  • R, R R1,. r and s have the meanings indicated ence of a metal or a metal compound.
  • an agent capable 0 means hydrogen (H or oxygen. of eliminating the hydrogenhalide formed during the condensation reaction.
  • an agent capable 0 such as hydrogen (H or oxygen. of eliminating the hydrogenhalide formed during the condensation reaction.
  • such as pyridine. triethylamine. etc.. is usually added to the reaction mixture.
  • the condensation reaction can be performed in any suitable solvent. Where methylenehalide is used as the reagent lII. special preference is given to an aprotic polar solvent. such as dimethylsulfoxide. sulfolane or acetonitril. it is also possible. however. to perform the condensation exclusively in the reagent lll. so ina(additional) solvent. in certain cases. e.g. in the absence of any (additional) urea is used as the reagent ill. the condensation can be carried out in a melt.
  • aprotic polar solvent such as dimethylsulfoxide. sulfolane or acetonitril.
  • the starting substances of formula II required in the present invention can be prepared by any process described for similar compounds.
  • the compound o-chloro-methyl-l lH-dibenzolb.e]azepinc can be reacted with a cyanate. for example sodiumcyanate.
  • the resulting nitrile may then either be reduced to the corresponding amino compound optionally followed by introduction of the desired R;.-group.
  • the substituent 1 R1.) at the N nitrogen atom can also be obtained after the condensation reaction by alkylating or aralkylating the unsubstituted nitrogen atom (R H) or by acylating the unsubstituted nitrogen atom followed by a reduction of the carbonyl moiety of the N-acyl compound thus obtained.
  • the compounds according to the present invention have as already mentioned a completely different pharmacological profile with respect to the related known piperazinederivatives as described in the British Pat. No. 1.229.252.
  • the present compounds show a positive effect in the reserpine-antagonism test and in the reserpine-reversal test. which means that they can be applied as antideing a compound ll ith Q H2. or be hydr lysed and 20 pressive agents.
  • the present compounds possess more optionally followed by introduction of the R;.-group. so generally strong CNS stimulatroy properties which toforming a compound H in which oxygen. gether with their effects against agression means that
  • the acid addition salts of the compounds according the compounds of the present invention have also poto the invention are prepared in conventional manner tent anxioly tic properties. by reacting the free base with a pharmaceutically ach They can be administered both orally and parenterceptable acid such as hydrochloric acid.
  • hydrobromic ally preferably in a dosage of between 0.0l and mg acid or hydroiodic acid.
  • phosphoric acid preferably acetic acid.
  • P g Y Weight Mixed with Suitable auxiliaries he propionic acid. glycollic acid. maleic acid. malonic Compounds can be compressed into said dosage units.
  • aicd succinic acid. tartaric acid. citric acid. ascorbic
  • Such 115 P filbleiS n Coated lets. They Can also id, li li acid or b i id, be processed into capsules.
  • the pharmaceutically acceptable quaternary ammo- Y means of Suitable liquids the compounds I can nium compounds, in particular the lower l4C) alkyl f applied injection Preparations in the form of Soluquaternary ammonium compounds. are obtained by ret10n5- emulsiflns Suspensions acting the compounds of the general formula I with an P which are Preferably used in Present alkyl halide. for example methyl iodide or methyl bromide.
  • a hydroxy group present can be acylated or converted into an alkoxy
  • the following examples serve to illustrate the invengroup. an amino group into a halogen group. a metion further. In the examples the following nomenclathyoxy group into a hydroxy group. etc. ture and numbering have been used:
  • the solution is set aside at 20C'for 30 minutes, after which it is poured out into 250 ml of water and extracted 3x with methylene chloride, washed with water and evaporated by means of a film evaporator.
  • the remaining oil is purified by means of a chromatographic column (the solvent mixture is benzenermethanol (9:I)). Rf in benzenermethanol (822) 0.50 on $0,.
  • a solution of L2 g ofthiophosgene in l0 ml oftoluene is gently added. at 0C. to a solution of 2.4 g of 6-aminoethyl-5.o-dihydro-l lH-dibenzo[b.e]azepine in 20 ml of toluene to which 5 ml of pyridine have been added.
  • the reaction mixture is left to stand for 1 hour and after that 20 ml of water are added.
  • the mixture is stirred vigorously. after which the water layer is separated trom the toluene layer.
  • the toluene phase is washed with water. then with 0.2 M sulphuric acid and finally with water.
  • the benzene extracts are processed in the conventional manner.
  • EXAMPLE XIV a Z-kcto-l.2.3.4.l().l4b-hexahydro-pyrimidino[3.4- a]dibenzo[c.f]azepine 10 g of 6-carboxamidomethyl-5.6 dihydromorphanthridine is dissolved in 300 ml ethanol (70%). After which H1O ml of a 37% formaldehyde solution in water is added. The mixture is refluxed for 6 hours. after which the solvent is substantially evaporated. The resi due obtained is filtered and the solid substance dried.
  • the group NR. and CH R. and R are selected from the group consisting of hydrogen. halogen. hydroxy. alkyl having [-6 carm bon atoms. alkoxy having l6 carbon atoms. and trifluoromethyl;
  • R is selected from the group consisting of hydrogen.
  • alkyl having 1-6 carbon atoms. and R. is selected from the group consisting of hydrogen 7S and alkyl having l-o carbon atoms. and the pharinaceutically acceptable acid addition salts and quaternary ammonium compounds thereof.
  • X is CH- 3.
  • X is oxygen.
  • X O 1l-aminoethyl-l0,ll-dihydrodibenzo[b,f](1,4)oxazepine
  • X S ll -aminoethyll0,1l-dihydrodibenzofbfi](1,4)thiazepine
  • X N ll--aminoethy1-10,ll-dihydro- 5H-dibenzo[b,e](1,4)diazepine.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Epidemiology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Biomedical Technology (AREA)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • Psychiatry (AREA)
  • Pain & Pain Management (AREA)
  • Anesthesiology (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
US396251A 1972-09-23 1973-09-07 Pyrimidino-dibenzo-azepine,-oxazepine,-thiazepine and diazepine derivatives Expired - Lifetime US3892695A (en)

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NLAANVRAGE7212915,A NL176458C (nl) 1972-09-23 1972-09-23 Werkwijze ter bereiding van een farmaceutisch preparaat en werkwijze voor de bereiding van daartoe geschikte actieve stoffen.

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JP (1) JPS5912678B2 (es)
AR (1) AR203090A1 (es)
AU (1) AU472312B2 (es)
BE (1) BE805178A (es)
CA (1) CA1019733A (es)
CH (1) CH592094A5 (es)
DE (1) DE2347727C2 (es)
DK (1) DK140668B (es)
ES (1) ES418996A1 (es)
FI (1) FI54311C (es)
FR (1) FR2199996B1 (es)
GB (1) GB1445765A (es)
HU (1) HU167206B (es)
IE (1) IE38221B1 (es)
NL (1) NL176458C (es)
SE (1) SE407686B (es)
ZA (1) ZA737131B (es)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4039558A (en) * 1974-10-28 1977-08-02 Akzona Incorporated Amino-substituted tetracyclic compounds
US4056529A (en) * 1975-01-16 1977-11-01 John Wyeth & Brother Limited Dibenzopyrimidoazepines
US4217452A (en) * 1974-02-09 1980-08-12 Akzona Incorporated Synthesis for the preparation of tetracyclic compounds
US4224321A (en) * 1976-02-10 1980-09-23 Akzona Incorporated Biologically active tetracyclic compounds and pharmaceutical compositions containing same
US4254031A (en) * 1974-02-09 1981-03-03 Akzona Incorporated Synthesis for the preparation of tetracyclic compounds
US4284559A (en) * 1978-09-26 1981-08-18 Akzona Incorporated 10-Hydroxy-1,2,3,4,10,14b-hexahydrodibenzo-[c,f] pyrazino-1,2a-azepines

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
HU195491B (en) * 1985-12-20 1988-05-30 Egyt Gyogyszervegyeszeti Gyar Process for production of optically active 2-chlor-12-/3-/dimethil-amin/-2-methil-prophil/-12h-dibenzol /d,g/ /1,3,6/-diaxazocine and medical compositions containing such compounds
CH678623A5 (en) * 1989-05-17 1991-10-15 Sochinaz Societe Chimique De V Prepn. of di:benzo pyrazino azepine(s)

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3470181A (en) * 1967-10-23 1969-09-30 American Home Prod Fused 2-pyrimidinepropionic acid compounds,related compounds,and the process for their preparation

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL154511B (nl) * 1967-07-07 1977-09-15 Organon Nv Werkwijze ter bereiding van piperazinederivaten, werkwijze ter bereiding van een farmaceutisch preparaat, dat een dergelijke verbinding bevat en vormstukken bereid volgens deze werkwijze.

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3470181A (en) * 1967-10-23 1969-09-30 American Home Prod Fused 2-pyrimidinepropionic acid compounds,related compounds,and the process for their preparation

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4217452A (en) * 1974-02-09 1980-08-12 Akzona Incorporated Synthesis for the preparation of tetracyclic compounds
US4254031A (en) * 1974-02-09 1981-03-03 Akzona Incorporated Synthesis for the preparation of tetracyclic compounds
US4039558A (en) * 1974-10-28 1977-08-02 Akzona Incorporated Amino-substituted tetracyclic compounds
US4056529A (en) * 1975-01-16 1977-11-01 John Wyeth & Brother Limited Dibenzopyrimidoazepines
US4224321A (en) * 1976-02-10 1980-09-23 Akzona Incorporated Biologically active tetracyclic compounds and pharmaceutical compositions containing same
US4284559A (en) * 1978-09-26 1981-08-18 Akzona Incorporated 10-Hydroxy-1,2,3,4,10,14b-hexahydrodibenzo-[c,f] pyrazino-1,2a-azepines

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BE805178A (fr) 1974-03-21
CH592094A5 (es) 1977-10-14
IE38221B1 (en) 1978-01-18
NL7212915A (es) 1974-03-26
DE2347727A1 (de) 1974-04-04
DE2347727C2 (de) 1986-12-11
ZA737131B (en) 1974-08-28
NL176458B (nl) 1984-11-16
FR2199996A1 (es) 1974-04-19
FI54311C (fi) 1978-11-10
FR2199996B1 (es) 1977-09-09
JPS4985098A (es) 1974-08-15
AR203090A1 (es) 1975-08-14
AU472312B2 (en) 1976-05-20
HU167206B (es) 1975-09-27
NL176458C (nl) 1985-04-16
SE407686B (sv) 1979-04-09
JPS5912678B2 (ja) 1984-03-24
GB1445765A (en) 1976-08-11
DK140668C (es) 1980-03-24
DK140668B (da) 1979-10-22
ES418996A1 (es) 1976-07-01
AU6019773A (en) 1975-03-13
FI54311B (fi) 1978-07-31
IE38221L (en) 1974-03-23
CA1019733A (en) 1977-10-25

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