EP0619820A1 - Imidazoquinazoline compounds and their preparation and use - Google Patents

Imidazoquinazoline compounds and their preparation and use

Info

Publication number
EP0619820A1
EP0619820A1 EP93902092A EP93902092A EP0619820A1 EP 0619820 A1 EP0619820 A1 EP 0619820A1 EP 93902092 A EP93902092 A EP 93902092A EP 93902092 A EP93902092 A EP 93902092A EP 0619820 A1 EP0619820 A1 EP 0619820A1
Authority
EP
European Patent Office
Prior art keywords
compound
cyclopropyl
quinazoline
imidazo
oxadiazol
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.)
Withdrawn
Application number
EP93902092A
Other languages
German (de)
English (en)
French (fr)
Inventor
Holger Claus Hansen
Marit Kristiansen
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Novo Nordisk AS
Original Assignee
Novo Nordisk AS
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
Application filed by Novo Nordisk AS filed Critical Novo Nordisk AS
Publication of EP0619820A1 publication Critical patent/EP0619820A1/en
Withdrawn legal-status Critical Current

Links

Classifications

    • 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
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • 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
    • A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
    • 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
    • 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
    • A61P25/08—Antiepileptics; Anticonvulsants
    • 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

Definitions

  • the present invention relates to therapeutically active imidazoquinazoline compounds, a method of preparing the same, pharmaceutical compositions comprising the compounds, and to methods of treating therewith.
  • the novel compounds are useful in psychopharmaceutical applications, e.g. in the treatment of central nervous system ailments, for example as anticonvul- sants, anxiolytics, hypnotics, antipsychotics, antiemetics, in improving the cognitive function of the brain of mammals, or as benzodiazepine antagon- ists.
  • R 1 is hydrogen, straight or branched C ⁇ -alkyl, unsubstituted or C ⁇ -alkyl substituted G ⁇ -cycloalkyl, C ⁇ -alkoxy, C ⁇ -alkoxy-C ⁇ -alkyl or tri- fluoromethyl;
  • R 8 is straight or branched C 1-6 -alkyl;
  • R 2 and R 3 independently are hydrogen, C ⁇ -alkyl, optionally substituted with C ⁇ -cycIoalkyl, di-C ⁇ -alkylamino, phenyl or a p ⁇ peridinyl group optionally substituted with C ⁇ -alkyl, or R 2 and R 3 independently are C ⁇ -cycloalkyl,
  • R 4 , R 5 , R 6 and R 7 independently are hydrogen, hydroxy, CI, Br, F, I, triffuoro- methyl, nitro, amino, cyano, straight or branched C ⁇ -alkyl, C 2 ⁇ -alkenyl, C 2 ⁇ - alkynyl, C ⁇ -alkoxy, C ⁇ -alkoxy-C ⁇ -alkyl or C ⁇ -alkoxycarbonyl;
  • R 4 , R 5 , R 6 , R 7 at the same time cannot all be hydrogen when Q is
  • R 1' is H, C ⁇ -alkyl or unsubstituted C ⁇ -cycloalkyl
  • R 2 and R 3 independently are H, C ⁇ -alkoxy, C ⁇ -cycloalkyl or C ⁇ -alkyl or NR 2 R 3 forms an unsubstituted morpholino or thiomorpholino group
  • the compound of formula I is not ethyl 6-chloro-5-morpholino-imidazo[1 ,5-a]quinazoiine-3- carboxylate or 6-chloro-3-(3-cyclopropyl-1 ,2,4-oxadiazol-5-yl)-5-morpholino- imidazo[1 ,5-a]quinazoline.
  • the invention also relates to methods of preparing the above-mentioned compounds. These methods comprise:
  • R 2 , R 3 , R 4 , R 5 , R 6 and R 7 are as defined above and wherein Y is a leaving group, with a compound having the formula III
  • R 1 is as defined above to form a compound of the general formula I wherein Q is
  • R 1 is as defined above, or
  • R 2 , R 3 , R 4 , R 5 , R 8 and R 7 have the meanings set forth above, with a dehydrating agent to form a compound of formula I, wherein R 2 , R 3 , R 4 , R 5 , R 6 and R 7 have the meanings set forth above and wherein Q is cyano, or
  • R 2 , R 3 , R 4 , R 5 , R 8 and R 7 have the meanings set forth above, with NH 2 OH to form a compound of formula VIII
  • R 2 , R 3 , R 4 , R 5 , R 8 and R 7 have the meanings set forth above, and reacting the compound of formula VIII with R 1 -COOEt or with (R 1 CO) 2 0, wherein R 1 is as defined above to form a compound of the general formula I wherein Q is
  • the leaving group, Y may be any suitable leaving group and, for example, those disclosed in U.S. Patents 4,031 ,079 or 4,359,420, for example, halogen, alkylthio, for example methylthio, ar alkylthio, N-nitrosoalkylamino, alkoxy, mercapto, -0P(0)(0R) 2 wherein R is lower-alkyl or -OP(0)(NR'R") 2 wherein R' and R" each represents lower-alkyl or phenyl, or together with the nitrogen atom to which they are attached represent a heterocyclic radical such as morpholino, pyrrolidino, piperidino, or methylpiperazinyl.
  • the reaction is preferably carried out under alkaline conditions, i.e., in the presence of a base, and among bases alkali metal (e.g., potassium or sodium) alkoxides or hydrides are preferred.
  • the reaction is preferably conducted in the presence of an organic solvent which is nonreactive with the reactants and products of reaction under the conditions of reaction, especially an anhydrous solvent and preferably and anhydrous aprotic solvent such as dimethylformamide (DMF), tetrahydrofuran (THF), or the like.
  • the temperature range employed may be any range suitable for the reaction to proceed at a reasonable rate and without undue delay or decomposition and a range from -40°C to about room temperature is accordingly usually particularly suitable.
  • the starting materials employed in the syntheses of the compounds of formula I are either known or may be prepared in conventional manner from commercially available materials, e.g. according to Karminski et al., J. Environ. Sci. Health, Part B, 1983 B 18 (4-5) 599.
  • the pharmaceutical properties of the compounds of the invention can be illustrated by determining their capability for displacing radioactive labelled flunitrazepam from benzodiazepine receptors.
  • the displacement activity of the compounds of the invention may be found by determining the ED ⁇ value.
  • the ED ⁇ value represents the dose (mg/kg) of a test substance which causes the specific binding of 3 H-flunitrazepam to benzodiazepine receptors in a living brain to be reduced to 50% of the control value.
  • the compounds of the invention together with a conventional adjuvant, carrier, or diluent, and if desired in the form of a pharmaceutically accept ⁇ able acid addition salt thereof, may be placed into the form of pharmaceuti- cal compositions and unit dosages thereof, and in such form may be em ⁇ ployed as solids, such as tablets or filled capsules, or liquids, such as solutions, suspensions, emulsions, elixirs, or capsules filled with the same, all for oral use, in the form of suppositories for rectal administration; or in the form of sterile injectable solutions for parenteral (including sub- cutaneous) use.
  • Such pharmaceutical compositions and unit dosage forms thereof may comprise conventional ingredients in conventional proportions, with or without additional active compounds or principles, and such unit dosage forms may contain any suitable effective central nervous system ailment alleviating amount of the active ingredient commensurate with the intended daily dosage range to be employed.
  • the compounds of the invention can thus be used for the formulation of pharmaceutical preparations, e.g. for oral and parenteral administration to mammals including humans, in accordance with conventional methods of galenic pharmacy.
  • Conventional excipients are such pharmaceutically acceptable organic or inorganic carrier substances suitable for parenteral or oral application which do not deleteriously react with the active compound.
  • E ⁇ xamples of such carriers are water, salt solutions, alcohols, polyethylene glycols, polyhydroxyethoxylated castor oil, gelatin, lactose, amylose, mag ⁇ nesium stearate, talc, silicic acid, fatty acid monoglycerides and diglyce- rides, pentaerythritol fatty acid esters, hydroxymethylcellulose and polyvinyl- pyrrolidone.
  • the pharmaceutical preparations can be sterilized and mixed, if desired, with auxiliary agents, such as lubricants, preservatives, stabilizers, wetting agents, emulsifiers, salt for influencing osmotic pressure, buffers and/or colouring substances and the like, which do not deleteriously react with the active compound.
  • auxiliary agents such as lubricants, preservatives, stabilizers, wetting agents, emulsifiers, salt for influencing osmotic pressure, buffers and/or colouring substances and the like, which do not deleteriously react with the active compound.
  • injectable solutions or suspensions preferably aqueous solutions with the active compound dissolved in polyhydroxylated castor oil.
  • Ampoules are convenient unit dosage forms.
  • tablets, dragees, or capsules having talc and/or a carbohydrate carrier or binder or the like, the carrier preferably being lactose and/or corn starch and/or potato starch.
  • a syrup, elixir or the like can be used when a sweetened vehicle can be employed.
  • the compounds of the invention are dispensed in unit dosage form comprising 0.05-100 mg in a pharmaceuti ⁇ cally acceptable carrier per unit dosage.
  • a typical tablet which may be prepared by conventional tabletting tech- niques contains:
  • the compounds of the invention are extremely useful in the treatment of central nervous system ailments or disorders, when administered in an amount effective for the alleviation, amelioration, or elimination thereof.
  • the import ⁇ ant CNS activity of the compounds of the invention includes both anti- convulsant, anxiolytic, hypnotic, antipsychotic, and antiemetic activities and activity as to improvement of the cognitive function of the brain of mammals along with a low toxicity, together presenting a most favourable therapeutic index.
  • the compounds of the invention may accordingly be administered to a subject, e.g.
  • a living mammal body including a human, in need of the same for the treatment, alleviation, amelioration, or elimination of an indica- tion, associated with the central nervous system and the so-called benzo ⁇ diazepine receptors, which requires such psychopharmaceutical treatment, e.g. especially convulsion, insomnia, anxiety, psychosis, emesis, dementia states and/or as benzodiazepine antagonists, if desired in the form of a pharmaceutically acceptable acid addition salt thereof (such as the hydro- bromide, hydrochloride, tartrate or sulphate, in any event prepared in the usual or conventional manner, e.g.
  • a pharmaceutically acceptable acid addition salt thereof such as the hydro- bromide, hydrochloride, tartrate or sulphate, in any event prepared in the usual or conventional manner, e.g.
  • a pharmaceutically acceptable carrier or diluent especially and preferably in the form of a pharmaceutical composition thereof, whether by oral, rectal, or parenteral (including subcutaneous) route, in an effective psychopharmaceutical central nervous system ailment alleviating amount, e.g. an anticonvulsant, anxiolytic, hypnotic and/or antipsychotic amount, and in any event an amount which is effective for the alleviation of such a central nervous system ailment due to their benzodiazepine receptor affinity.
  • an effective psychopharmaceutical central nervous system ailment alleviating amount e.g. an anticonvulsant, anxiolytic, hypnotic and/or antipsychotic amount, and in any event an amount which is effective for the alleviation of such a central nervous system ailment due to their benzodiazepine receptor affinity.
  • Suitable dosage ranges are 1-200 milligrams daily, 1-100 milligrams daily, and especially 1-30 milligrams daily, depending as usual upon the exact mode of administration, form in which administered, the indication toward which the administration is directed, the subject involved and the body weight of the subject involved, and the preference and experience of the physician or veterinarian in charge.
  • 6-Chloro-3-(3-cyclopro ⁇ yl-1 ,2,4-oxadiazol-5-yl)-5-morpholi ⁇ o-imidazo[1,5-a]- quiriazoline (1.45 g) in 25 ml of 6 M aqueous hydrochloric acid was stirred at 100°C for 45 min. Then the mixture was cooled to 0°C and the precipi ⁇ tated crystals were filtered off, rinsed on the filter with 25 ml of water, then with 5 x 1 ml of ethyl acetate, and finally with 10 ml of diethyl ether. The beige crystals were dried, yielding 0.85 g of the title compound, m.p. 270- 272°C (decomp.).
  • Trifluoroacet ⁇ c anhydride (0.15 ml) was added dropwise to a suspension of 5-morpholino-imidazo[1,5-a]quinazoline-3-carboxamide oxime in 4 ml of dry tetrahydrofuran. After stirring for 3 hours at room temperature the reaction mixture was evaporated in vacuo. The residue was dissolved in a mixture of water and ethyl acetate. The organic phase was washed with water, dried over anhydrous magnesium sulphate, and evaporated to dryness. The crystals were rinsed by stirring with isopropanol (3 ml) to give yellow crystals of the title compound, m.p. 182-186°C. Yield 0.06 g.
  • Glacial acetic acid (2 mi) and dichloromethane (50 ml) were added, and after the precipitated product had dissolved the sieves were removed by filtration through celite. The filtrate was evaporated and the residue was triturated with 100 ml of water. The undissolved material was collected by filtration, dried and treated with 25 ml of acetone. Yellow crystals precipi ⁇ tated and were filtered off and dried. Yield 0.47 g, m.p. 262-264°C.

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Medicinal Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Biomedical Technology (AREA)
  • Engineering & Computer Science (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Epidemiology (AREA)
  • Anesthesiology (AREA)
  • Pain & Pain Management (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Plural Heterocyclic Compounds (AREA)
EP93902092A 1991-12-20 1992-12-18 Imidazoquinazoline compounds and their preparation and use Withdrawn EP0619820A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DK912042A DK204291D0 (da) 1991-12-20 1991-12-20 Heterocykliske forbindelser deres fremstilling og anvendelse
DK2042/91 1991-12-20
PCT/DK1992/000385 WO1993013103A1 (en) 1991-12-20 1992-12-18 Imidazoquinazoline compounds and their preparation and use

Publications (1)

Publication Number Publication Date
EP0619820A1 true EP0619820A1 (en) 1994-10-19

Family

ID=8109668

Family Applications (1)

Application Number Title Priority Date Filing Date
EP93902092A Withdrawn EP0619820A1 (en) 1991-12-20 1992-12-18 Imidazoquinazoline compounds and their preparation and use

Country Status (12)

Country Link
EP (1) EP0619820A1 (enrdf_load_stackoverflow)
JP (1) JPH07502278A (enrdf_load_stackoverflow)
AU (1) AU673814B2 (enrdf_load_stackoverflow)
CA (1) CA2125854A1 (enrdf_load_stackoverflow)
DK (1) DK204291D0 (enrdf_load_stackoverflow)
FI (1) FI942963A7 (enrdf_load_stackoverflow)
IL (1) IL104099A (enrdf_load_stackoverflow)
NO (1) NO942301L (enrdf_load_stackoverflow)
NZ (1) NZ246558A (enrdf_load_stackoverflow)
TW (1) TW211568B (enrdf_load_stackoverflow)
WO (1) WO1993013103A1 (enrdf_load_stackoverflow)
ZA (1) ZA929770B (enrdf_load_stackoverflow)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DK151890D0 (da) * 1990-06-22 1990-06-22 Ferrosan As Heterocykliske forbindelser deres fremstilling og brug
CN1052724C (zh) * 1996-07-01 2000-05-24 瑞安大药厂股份有限公司 新的光学活性的2,3－二氢咪唑并[1,2－c]喹唑啉衍生物及其制备方法和用途
KR100864364B1 (ko) 2005-12-13 2008-10-17 주식회사 엘지화학 신규한 이미다조퀴나졸린 유도체, 이의 제조방법 및 이를이용한 유기전기소자
EP2125750B1 (en) 2007-02-26 2014-05-21 Vitae Pharmaceuticals, Inc. Cyclic urea and carbamate inhibitors of 11beta-hydroxysteroid dehydrogenase 1
AR069207A1 (es) 2007-11-07 2010-01-06 Vitae Pharmaceuticals Inc Ureas ciclicas como inhibidores de la 11 beta - hidroxi-esteroide deshidrogenasa 1
US8440658B2 (en) 2007-12-11 2013-05-14 Vitae Pharmaceuticals, Inc. Cyclic urea inhibitors of 11β-hydroxysteroid dehydrogenase 1
DK2324018T3 (da) 2008-07-25 2013-10-14 Boehringer Ingelheim Int Cykliske inhibitorer af 11 beta-hydroxysteroid dehydrogenase 1
TW201016691A (en) 2008-07-25 2010-05-01 Boehringer Ingelheim Int Inhibitors of 11beta-hydroxysteroid dehydrogenase 1
WO2010089303A1 (en) 2009-02-04 2010-08-12 Boehringer Ingelheim International Gmbh CYCLIC INHIBITORS OF 11 β-HYDROXYSTEROID DEHYDROGENASE 1
UA109255C2 (ru) 2009-04-30 2015-08-10 Берінгер Інгельхайм Інтернешнл Гмбх Циклические ингибиторы 11бета-гидроксистероиддегидрогеназы 1
US8927539B2 (en) 2009-06-11 2015-01-06 Vitae Pharmaceuticals, Inc. Cyclic inhibitors of 11β-hydroxysteroid dehydrogenase 1 based on the 1,3-oxazinan-2-one structure
EP2448928B1 (en) 2009-07-01 2014-08-13 Vitae Pharmaceuticals, Inc. Cyclic inhibitors of 11beta-hydroxysteroid dehydrogenase 1
EP2582698B1 (en) 2010-06-16 2016-09-14 Vitae Pharmaceuticals, Inc. Substituted 5-,6- and 7-membered heterocycles, medicaments containing such compounds, and their use
WO2011161128A1 (en) 2010-06-25 2011-12-29 Boehringer Ingelheim International Gmbh Azaspirohexanones as inhibitors of 11-beta-hsd1 for the treatment of metabolic disorders
CA2813671A1 (en) 2010-11-02 2012-05-10 Boehringer Ingelheim International Gmbh Pharmaceutical combinations for the treatment of metabolic disorders
JP2023545196A (ja) * 2020-10-16 2023-10-26 シャンハイ ドーァ ノボ ファーマテック カンパニー，リミティド 三複素環誘導体、その医薬組成物及び使用

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CA1297099C (en) * 1985-10-17 1992-03-10 Frank Watjen Quinazoline compounds and their preparation and use
DK155524C (da) * 1987-03-18 1989-09-11 Ferrosan As Kondenserede imidazolderivater og farmaceutiske praeparater indeholdende disse
DK443589D0 (da) * 1989-09-08 1989-09-08 Ferrosan As Heterocykliske forbindelser, deres fremstilling og anvendelse
DK151890D0 (da) * 1990-06-22 1990-06-22 Ferrosan As Heterocykliske forbindelser deres fremstilling og brug

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9313103A1 *

Also Published As

Publication number Publication date
IL104099A0 (en) 1993-05-13
AU3344893A (en) 1993-07-28
NZ246558A (en) 1995-07-26
ZA929770B (en) 1994-06-17
FI942963L (fi) 1994-06-20
CA2125854A1 (en) 1993-07-08
WO1993013103A1 (en) 1993-07-08
JPH07502278A (ja) 1995-03-09
IL104099A (en) 1996-07-23
AU673814B2 (en) 1996-11-28
DK204291D0 (da) 1991-12-20
NO942301L (no) 1994-08-19
TW211568B (enrdf_load_stackoverflow) 1993-08-21
FI942963A0 (fi) 1994-06-20
FI942963A7 (fi) 1994-06-20
NO942301D0 (no) 1994-06-17

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