NO874780L - ANALOGUE PROCEDURE FOR THE PREPARATION OF THERAPEUTIC ACTIVE PYRROLO-BENZIMIDAZOLE DERIVATIVES. - Google Patents

ANALOGUE PROCEDURE FOR THE PREPARATION OF THERAPEUTIC ACTIVE PYRROLO-BENZIMIDAZOLE DERIVATIVES.

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Publication number
NO874780L
NO874780L NO874780A NO874780A NO874780L NO 874780 L NO874780 L NO 874780L NO 874780 A NO874780 A NO 874780A NO 874780 A NO874780 A NO 874780A NO 874780 L NO874780 L NO 874780L
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dimethyl
group
pyrrolo
dihydro
benzimidazol
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NO874780A
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Norwegian (no)
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NO874780D0 (en
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Berthold Narr
Norbert Hauel
Klaus Noll
Joachim Heider
Manfred Psiorz
Andreas Bomhard
Jacques Van Meel
Willi Diederen
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Thomae Gmbh Dr K
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Publication of NO874780D0 publication Critical patent/NO874780D0/en
Publication of NO874780L publication Critical patent/NO874780L/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
    • C07D209/32—Oxygen atoms
    • C07D209/34—Oxygen atoms in position 2
    • 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
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Veterinary Medicine (AREA)
  • Engineering & Computer Science (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Diabetes (AREA)
  • Hematology (AREA)
  • Cardiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Description

I DE-A1-3.501.497 er det allerede beskrevet pyrrolo-benzimidazoler som er substituert i 5-stilling samt legemidler for behandling av hjerte- og kretsløpssykdommer som inneholder disse forbindelsene. DE-A1-3,501,497 already describes pyrrolo-benzimidazoles which are substituted in the 5-position as well as pharmaceuticals for the treatment of heart and circulatory diseases which contain these compounds.

Det er nå funnet at de nye 5-substituerte pyrrolo-benzimidazoler med formel It has now been found that the new 5-substituted pyrrolo-benzimidazoles of formula

hvor where

A og B sammen med de to mellomliggende karbonatomer utgjør en imidazogruppe med formel A and B together with the two intermediate carbon atoms form an imidazo group with formula

og deres syreaddisjonssalter, og for den farmasøytiske anvendelse, spesielt deres fysiologisk akseptable syreaddisjonssalter med uorganiske eller organiske syrer, oppviser overlegne farmakologiske egenskaper, særlig overlegne antitrombotiske og kardiovaskulære egenskaper. and their acid addition salts, and for the pharmaceutical use, especially their physiologically acceptable acid addition salts with inorganic or organic acids, exhibit superior pharmacological properties, especially superior antithrombotic and cardiovascular properties.

Foreliggende oppfinnelse angår en fremgangsmåte for fremstilling av de nye 5-substituerte pyrrolo-benzimidazoler med den ovenfor angitte formel I, deres syreaddisjonssalter, for den farmasøytiske anvendelse, spesielt deres fysiologisk akseptable syreaddisjonssalter. The present invention relates to a process for the preparation of the new 5-substituted pyrrolo-benzimidazoles with the above-mentioned formula I, their acid addition salts, for pharmaceutical use, especially their physiologically acceptable acid addition salts.

I den ovenfor angitte formel I betyrIn the above formula I means

R1et hydrogenatom eller en eventuelt med en fenylgruppe substituert alkylgruppe med 1-3 karbonatomer, R1 a hydrogen atom or an alkyl group optionally substituted by a phenyl group with 1-3 carbon atoms,

R2et hydrogenatom, en eventuelt med en fenyl-, pyridyl- eller tienylgruppe substituert alkylgruppe, en vinylengruppe som terminalt er substituert med en fenyl- eller pyridylgruppe, en eventuelt med et halogenatom, en hydroksy-, alkoksy-, merkapto-, alkylmerkapto-, alkylsulfinyl-, alkylsulfonyl-, cyano-, amino-, alkylamino-, dialkylamino-, alkanoylamino- eller nitrogruppe substituert fenylgruppe, hvor en hydroksyfenylgruppe dessuten kan være substituert med én eller to alkylgrupper som hver har 1-4 karbonatomer, eller hvor en aminofenylgruppe kan være substituert med ett eller to halogenatomer, en med halogenatomer, hydroksy-, alkoksy-, merkapto-, alkylmerkapto-, alkylsulfinyl-eller alkylsulfonylgrupper disubstituert fenylgruppe, hvor substituentene i fenylkjernen kan være like eller forskjellige, en via et karbonatom bundet 5- eller 6-leddet heteroaromatisk ring som inneholder et oksygen-, svovel- eller nitrogenatom, to eller tre nitrogenatomer eller ett nitrogenatom og ett oksygen-eller svovelatom, hvortil én eller to 1,4-butadienylgrupper kan være tilknyttet via to nabostilte karbonatomer, idet bindingen i dette tilfelle også kan skje via en tilkondensert fenylring, og, når det gjelder pyridinene, disse ytterligere kan være substituert med en amino-, alkylamino-, dialkylamino-, alkanoylamino- eller morfolinogruppe, eller med to halogenatomer eller med ett halogenatom og én amino- eller morfolinogruppe, og når det gjelder kinolinene, disse ytterligere kan være mono- eller disubstituert med et halogenatom, en alkoksy- eller fenylgruppe, idet substituentene kan være like eller forskjellige, en via et karbonatom bundet 5- til 7-leddet mettet imino-, N-alkylimino-eller N-alkanoylimino-alkylenring, en 1,2,3,4-tetrahydrokinolyl-eller 5,6,7,8-tetrahydrokinolylgruppe, hvor alle ovenfor ved definisjon av resten R2nevnte ringer kan være substituert med en alkylgruppe, og alkyldelen av alle ovenfor nevnte grupper, om intet annet er angitt, hver kan inneholde 1-3 karbonatomer og alkanoyldelen 2 eller 3 karbonatomer, R2 a hydrogen atom, an optionally substituted alkyl group with a phenyl, pyridyl or thienyl group, a vinylene group which is terminally substituted with a phenyl or pyridyl group, an optionally with a halogen atom, a hydroxy-, alkoxy-, mercapto-, alkylmercapto-, alkylsulfinyl -, alkylsulfonyl-, cyano-, amino-, alkylamino-, dialkylamino-, alkanoylamino- or nitro-substituted phenyl group, where a hydroxyphenyl group may also be substituted by one or two alkyl groups each having 1-4 carbon atoms, or where an aminophenyl group may be substituted with one or two halogen atoms, a disubstituted phenyl group with halogen atoms, hydroxy, alkoxy, mercapto, alkylmercapto, alkylsulfinyl or alkylsulfonyl groups, where the substituents in the phenyl nucleus can be the same or different, a 5- or 6- membered heteroaromatic ring containing one oxygen, sulfur or nitrogen atom, two or three nitrogen atoms or one nitrogen atom and one oxygen atom is a sulfur atom, to which one or two 1,4-butadienyl groups can be attached via two neighboring carbon atoms, as the bond in this case can also take place via a fused phenyl ring, and, in the case of the pyridines, these can further be substituted with an amino, alkylamino, dialkylamino, alkanoylamino or morpholino group, or with two halogen atoms or with one halogen atom and one amino or morpholino group, and in the case of the quinolines, these may further be mono- or disubstituted with a halogen atom, an alkoxy or phenyl group, wherein the substituents can be the same or different, a 5- to 7-membered saturated imino-, N-alkylimino- or N-alkanoylimino-alkylene ring linked via a carbon atom, a 1,2,3,4-tetrahydroquinolyl-or 5,6, 7,8-tetrahydroquinolyl group, where all the rings mentioned above in the definition of the residue R2 can be substituted with an alkyl group, and the alkyl part of all the groups mentioned above, if nothing else is stated, each can contain 1-3 carbon atoms and the alkanoyl moiety 2 or 3 carbon atoms,

R3en eventuelt med en fenylgruppe substituert alkylgruppe, en alkylgruppe med 4-6 karbonatomer eller en alkylgruppe som fra 2- stillingen av, er substituert med en hydroksy-, alkoksy- R3 is optionally an alkyl group substituted with a phenyl group, an alkyl group with 4-6 carbon atoms or an alkyl group which, from the 2-position onwards, is substituted with a hydroxy,

eller pyridiniumgruppe, hvor hver alkyldel kan inneholde 1-3 karbonatomer, or pyridinium group, where each alkyl moiety may contain 1-3 carbon atoms,

R4og R5, som kan være like eller forskjellige, hydrogenatomer, alkylgrupper med 1-3 karbonatomer eller cykloalkylgrupper med 3- 7 karbonatomer. R 4 and R 5 , which may be the same or different, are hydrogen atoms, alkyl groups with 1-3 carbon atoms or cycloalkyl groups with 3-7 carbon atoms.

Aktuelle betydninger ifølge definisjonen av restene R1til R5, er for eksempel: for Rx hydrogen, en metyl-, etyl-, n-propyl-, isopropyl-, benzyl-, 1-fenyletyl-, 2-fenyletyl- eller 3-fenylpropylgruppe, for R2hydrogen, en metyl-, etyl-, n-propyl-, isopropyl-, benzyl-, 1-fenyletyl-, 2-fenyletyl-, 3-fenylpropyl-, pyridyl-metyl-, metylpyridylmetyl-, 1-pyridyletyl-, 2-pyridyletyl-, 2-fenyletenyl-, 2-pyridyletenyl-, fenyl-, fluorfenyl-, difluor-fenyl-, klorfenyl-, diklorfenyl-, bromfenyl-, dibromfenyl-, hydroksyfenyl-, dihydroksyfenyl-, metoksyfenyl-, dimetoksyfenyl-, merkaptofenyl-, bis(merkapto)fenyl-, metylmerkaptofenyl-, bis(metylmerkapto)fenyl-, metylsulfinylfenyl-, bis(metylsulfinyl)fenyl-, metylsulfonylfenyl-, bis(metylsulfonyl)fenyl-, fluor-hydroksyfenyl-, fluormetoksyfenyl-, fluormerkaptofenyl-, fluormetylmerkaptofenyl-, klorhydroksyfenyl-, klormetoksyfenyl-, klormerkaptofenyl-, klormetylmerkaptofenyl-, bromhydroksyfenyl-, brom-metoksyfenyl-, brom-merkaptofenyl-, brom-metylmerkaptofenyl-, hydroksymetoksyfenyl-, hydroksymerkaptofenyl-, hydroksy-metylmerkaptofenyl-, metoksymerkaptofenyl-, metoksymetylmerkapto-fenyl-, metoksymetylsulfinylfenyl-, metoksymetylsulfonylfenyl-, cyanofenyl-, aminofenyl-, metylaminofenyl-, dimetylaminofenyl-, acetylaminofenyl-, amino-diklorfenyl-, amino-dibromfenyl-, nitrofenyl-, 4-hydroksy-3,5-di-tert-butylfenyl-, pyridyl-, metylpyridyl-, etylpyridyl-, isopropylpyridyl-, 2-aminopyridyl-5-, 2-formylamino-pyridyl-5-, 2-acetylamino-pyridyl-5-, 2-propionylamino-pyridyl-5-, 2,6-diklor-pyridyl-4-, 2-klor-6-amino-pyridyl-4-, 2-klor-6-morfolino-pyridyl-4-, 2,6-diklor-pyridyl-3-, 2-klor-6-morfolino-pyridyl-3-, pyrrolyl-2-, pyrrolyl-3-, N-metyl-pyrrolyl-2-, N-etyl-pyrrolyl-2-, N-metyl-pyrrolyl-3-, N-etyl-pyrrolyl-3-, furyl-2-, furyl-3-, 5-metyl-furyl-2-, 2-metyl-furyl-3-, 5-metyl-furyl-3-, pyrazinyl-2-, pyrimidyl-2-, pyrimidyl-4-, pyrimidyl-5-, pyridazinyl-4-, benzo[b]furyl-2-, benzo[b]furyl-3-, 7-metyl-benzo[b]furyl-3-, tienyl-2-, tienyl-3-, tienyl-2-metyl-, tienyl-3-metyl-, 5-metyl-tienyl-2-, 2-metyl-tienyl-3-, 3-metyl-tienyl-2-, benzo-[b]tienyl-2-, benzo[b]tienyl-3-, benzo[b]tienyl-4-, benzo[b]-tienyl-5-, benzo[b]tienyl-6-, benzo[b]tienyl-7-, pyrazolyl-3-, imidazolyl-2-, imidazolyl-4(5)-, l-metyl-imidazolyl-4-, benzo[d]imidazolyl-2-, oksazolyl-2-, oksazolyl-4-, oksazolyl- Relevant meanings according to the definition of the residues R1 to R5 are, for example: for Rx hydrogen, a methyl, ethyl, n-propyl, isopropyl, benzyl, 1-phenylethyl, 2-phenylethyl or 3-phenylpropyl group, for R2hydrogen, a methyl-, ethyl-, n-propyl-, isopropyl-, benzyl-, 1-phenylethyl-, 2-phenylethyl-, 3-phenylpropyl-, pyridyl-methyl-, methylpyridylmethyl-, 1-pyridylethyl-, 2- pyridylethyl-, 2-phenylethenyl-, 2-pyridylethenyl-, phenyl-, fluorophenyl-, difluorophenyl-, chlorophenyl-, dichlorophenyl-, bromophenyl-, dibromophenyl-, hydroxyphenyl-, dihydroxyphenyl-, methoxyphenyl-, dimethoxyphenyl-, mercaptophenyl- , bis(mercapto)phenyl-, methylmercaptophenyl-, bis(methylmercapto)phenyl-, methylsulfinylphenyl-, bis(methylsulfinyl)phenyl-, methylsulfonylphenyl-, bis(methylsulfonyl)phenyl-, fluorohydroxyphenyl-, fluoromethoxyphenyl-, fluoromercaptophenyl-, fluoromethylmercaptophenyl -, chlorohydroxyphenyl-, chloromethoxyphenyl-, chloromercaptophenyl-, chloromethylmercaptophenyl-, bromohydroxyphenyl-, bromo-methoxyphenyl-, bromo-mercaptophenyl-, bromo-methylmercaptophen yl-, hydroxymethoxyphenyl-, hydroxymercaptophenyl-, hydroxy-methylmercaptophenyl-, methoxymercaptophenyl-, methoxymethylmercapto-phenyl-, methoxymethylsulfinylphenyl-, methoxymethylsulfonylphenyl-, cyanophenyl-, aminophenyl-, methylaminophenyl-, dimethylaminophenyl-, acetylaminophenyl, amino-dichlorophenyl-, amino- dibromophenyl-, nitrophenyl-, 4-hydroxy-3,5-di-tert-butylphenyl-, pyridyl-, methylpyridyl-, ethylpyridyl-, isopropylpyridyl-, 2-aminopyridyl-5-, 2-formylamino-pyridyl-5-, 2 -acetylamino-pyridyl-5-, 2-propionylamino-pyridyl-5-, 2,6-dichloro-pyridyl-4-, 2-chloro-6-amino-pyridyl-4-, 2-chloro-6-morpholino-pyridyl -4-, 2,6-dichloro-pyridyl-3-, 2-chloro-6-morpholino-pyridyl-3-, pyrrolyl-2-, pyrrolyl-3-, N-methyl-pyrrolyl-2-, N-ethyl -pyrrolyl-2-, N-methyl-pyrrolyl-3-, N-ethyl-pyrrolyl-3-, furyl-2-, furyl-3-, 5-methyl-furyl-2-, 2-methyl-furyl-3 -, 5-methyl-furyl-3-, pyrazinyl-2-, pyrimidyl-2-, pyrimidyl-4-, pyrimidyl-5-, pyridazinyl-4-, benzo[b]furyl-2-, benzo[b]furyl -3-, 7-methyl-benzo[b]furyl-3-, thienyl-2-, thienyl-3-, thienyl- 2-methyl-, thienyl-3-methyl-, 5-methyl-thienyl-2-, 2-methyl-thienyl-3-, 3-methyl-thienyl-2-, benzo-[b]thienyl-2-, benzo [b]thienyl-3-, benzo[b]thienyl-4-, benzo[b]-thienyl-5-, benzo[b]thienyl-6-, benzo[b]thienyl-7-, pyrazolyl-3-, imidazolyl-2-, imidazolyl-4(5)-, l-methyl-imidazolyl-4-, benzo[d]imidazolyl-2-, oxazolyl-2-, oxazolyl-4-, oxazolyl-

5-, 4-metyl-oksazolyl-5-, isoksazolyl-3-, 3-metyl-isoksazolyl-5-, 5-metyl-isoksazolyl-3-, tiazolyl-2-, tiazolyl-5-, 4-metyl-tiazolyl-5-, pyrazolyl-4-, triazolyl-3-, benzo[d]oksazolyl-2-, benzo[d]isoksazolyl-3-, benzo[d]tiazolyl-2-, benzo[d]isotiazolyl-3-, benzo[d]pyrazolyl-3-, indolyl-2-, indolyl-3-, 5-metyl-indolyl-3-, 7-metyl-indolyl-3-, N-metyl-indolyl-3-, kinolyl-2-, kinolyl-4-, isokinolyl-1-, 2-metyl-kinolyl-4-, 7-metyl-kinolyl-2-, 2-fenyl-kinolyl-4-, 2-klor-6-metoksy-kinolyl-4-, 4-klor-7-trifluormetyl-kinolyl-3-, 1,2,3,4-tetrahydro-kinolyl-2-, 1,2,3,4-tetrahydro-kinolyl-4-, 5,6,7,8-tetrahydro-kinolyl-2-, 5,6,7,8-tetrahydro-kinolyl-4-, akridinyl-6-, pyrrolidinyl-3-, piperidinyl-4-, heksahydro-azepinyl-4-, l-metylpiperidinyl-4-eller l-acetyl-piperidinyl-4-gruppe, 5-, 4-methyl-oxazolyl-5-, isoxazolyl-3-, 3-methyl-isoxazolyl-5-, 5-methyl-isoxazolyl-3-, thiazolyl-2-, thiazolyl-5-, 4-methyl-thiazolyl -5-, pyrazolyl-4-, triazolyl-3-, benzo[d]oxazolyl-2-, benzo[d]isoxazolyl-3-, benzo[d]thiazolyl-2-, benzo[d]isothiazolyl-3-, benzo[d]pyrazolyl-3-, indolyl-2-, indolyl-3-, 5-methyl-indolyl-3-, 7-methyl-indolyl-3-, N-methyl-indolyl-3-, quinolyl-2- , quinolyl-4-, isoquinolyl-1-, 2-methyl-quinolyl-4-, 7-methyl-quinolyl-2-, 2-phenyl-quinolyl-4-, 2-chloro-6-methoxy-quinolyl-4- , 4-chloro-7-trifluoromethyl-quinolyl-3-, 1,2,3,4-tetrahydro-quinolyl-2-, 1,2,3,4-tetrahydro-quinolyl-4-, 5,6,7, 8-tetrahydro-quinolyl-2-, 5,6,7,8-tetrahydro-quinolyl-4-, acridinyl-6-, pyrrolidinyl-3-, piperidinyl-4-, hexahydro-azepinyl-4-, 1-methylpiperidinyl- 4-or 1-acetyl-piperidinyl-4-group,

for R3en metyl-, etyl-, n-propyl-, isopropyl-, n-butyl-, isobutyl-, tert-butyl-, n-pentyl-, 1-metyl-n-butyl-, 2-metyl-n-butyl-, 3-metyl-n-butyl-, 1-etyl-n-propyl-, tert-pentyl-, n-heksyl-, 2-hydroksyetyl-, 2-hydroksy-n-propyl-, 3-hydroksy-n-propyl-, l-metyl-2-hydroksyetyl-, 2-metoksyetyl-, 2-etoksyetyl-, 2-metoksy-n-propyl-, 2-n-propoksy-n-propyl-, 3-metoksy-n-propyl-, 3-etoksy-n-propyl-, l-metyl-2-metoksyetyl-, l-metyl-2-isopropoksyetyl-, 2-pyridiniumetyl-, 3-pyridinium-n-propyl-, benzyl-, 1-fenyletyl-, 2-fenyletyl- eller 3-fenylpropylgruppe, for R3 is methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, 1-methyl-n-butyl, 2-methyl-n-butyl -, 3-methyl-n-butyl-, 1-ethyl-n-propyl-, tert-pentyl-, n-hexyl-, 2-hydroxyethyl-, 2-hydroxy-n-propyl-, 3-hydroxy-n- propyl-, 1-methyl-2-hydroxyethyl-, 2-methoxyethyl-, 2-ethoxyethyl-, 2-methoxy-n-propyl-, 2-n-propoxy-n-propyl-, 3-methoxy-n-propyl- , 3-ethoxy-n-propyl-, l-methyl-2-methoxyethyl-, l-methyl-2-isopropoxyethyl-, 2-pyridiniummethyl-, 3-pyridinium-n-propyl-, benzyl-, 1-phenylethyl-, 2-phenylethyl or 3-phenylpropyl group,

for R4og for R5hydrogen, en metyl-, etyl-, n-propyl-, isopropyl-, cyklopropyl-, cyklobutyl-, cyklopentyl-, cykloheksyl-eller cykloheptylgruppe. for R 4 and for R 5 hydrogen, a methyl, ethyl, n-propyl, isopropyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or cycloheptyl group.

I det følgende skal det nevnes forbindelser som faller inn under ovennevnte formel I, men som ikke eksplisitt er beskrevet i eksemplene: 5-metyl-2-(2-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benz-imidazol-6-on, In the following, mention must be made of compounds which fall under the above-mentioned formula I, but which are not explicitly described in the examples: 5-methyl-2-(2-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2, 3-f]benz-imidazol-6-one,

5-metyl-2-(4-metoksyfenyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]-benzimidazol-6-on, 5-methyl-2-(4-methoxyphenyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]-benzimidazol-6-one,

5-metyl-2-(4-hydroksyfenyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]-benzimidazol-6-on, 5-methyl-2-(4-hydroxyphenyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]-benzimidazol-6-one,

5-etyl-2-(4-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benz-imidazol-6-on, 5-ethyl-2-(4-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benz-imidazol-6-one,

5-etyl-2-(3-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benz-imidazol-6-on, 5-ethyl-2-(3-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benz-imidazol-6-one,

5-etyl-2-(2-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benz-imidazol-6-on, 5-ethyl-2-(2-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benz-imidazol-6-one,

5-etyl-2-(4-metoksyfenyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benz-imidazol-6-on, 5-ethyl-2-(4-methoxyphenyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benz-imidazol-6-one,

5-etyl-2-(4-hydroksyfenyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on, 5-ethyl-2-(4-hydroxyphenyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

5-(2-metoksyetyl)-2-(4-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on, 5-(2-Methoxyethyl)-2-(4-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

5-(2-metoksyetyl)-2-(3-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on, 5-(2-methoxyethyl)-2-(3-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

5-(2-metoksyetyl)-2-(2-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on, 5-(2-Methoxyethyl)-2-(2-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

5-(2-metoksyetyl)-2-(4-metoksyfenyl)-6,7-dihydro-3H,5H-pyrrolo-[2,3-f]benzimidazol-6-on, 5-(2-methoxyethyl)-2-(4-methoxyphenyl)-6,7-dihydro-3H,5H-pyrrolo-[2,3-f]benzimidazol-6-one,

5-(2-metoksyetyl)-2-(4-hydroksyfenyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on, 5-(2-methoxyethyl)-2-(4-hydroxyphenyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

5-(2-hydroksyetyl)-2-(4-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on, 5-(2-hydroxyethyl)-2-(4-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

5-(2-hydroksyetyl)-2-(3-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on, 5-(2-hydroxyethyl)-2-(3-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

5-(2-hydroksyetyl)-2-(2-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f ]benzirnidazol-6-on, 5-(2-Hydroxyethyl)-2-(2-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzirnidazol-6-one,

5-(2-hydroksyetyl)-2-(4-metoksyfenyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on, 5-(2-hydroxyethyl)-2-(4-methoxyphenyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

5-(2-hydroksyetyl)-2-(4-hydroksyfenyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on, 5-(2-hydroxyethyl)-2-(4-hydroxyphenyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

5,7-dimetyl-2-(4-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on, 5,7-dimethyl-2-(4-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

5,7-dimetyl-2-(3-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on, 5,7-dimethyl-2-(3-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

5,7-dimetyl-2-(2-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on, 5,7-dimethyl-2-(2-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

5,7-dimetyl-2-(4-metoksyfenyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on, 5,7-dimethyl-2-(4-methoxyphenyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

5,7-dimetyl-2-(4-hydroksyfenyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f Jbenzimidazol-6-on, 5,7-dimethyl-2-(4-hydroxyphenyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f Jbenzimidazol-6-one,

5-etyl-7-metyl-2-(3-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on, 5-ethyl-7-methyl-2-(3-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

5-etyl-7-metyl-2-(2-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on, 5-ethyl-7-methyl-2-(2-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

5-etyl-2-(4-metoksyfenyl)-7-metyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f ]benzimidazol-6-on', 5-ethyl-2-(4-methoxyphenyl)-7-methyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one',

5-etyl-2-(4-hydroksyfenyl)-7-metyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on, 5-ethyl-2-(4-hydroxyphenyl)-7-methyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

5-(2-metoksyetyl)-7-metyl-2-(4-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on, 5-(2-Methoxyethyl)-7-methyl-2-(4-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

5-(2-metoksyetyl)-7-metyl-2-(3-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on, 5-(2-Methoxyethyl)-7-methyl-2-(3-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

5-(2-metoksyetyl)-7-metyl-2-(2-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on, 5-(2-Methoxyethyl)-7-methyl-2-(2-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

5-(2-metoksyetyl)-2-(4-metoksyfenyl)-7-metyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on, 5-(2-methoxyethyl)-2-(4-methoxyphenyl)-7-methyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

5-(2-metoksyetyl)-2-(4-hydroksyfenyl)-7-metyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on, 5-(2-methoxyethyl)-2-(4-hydroxyphenyl)-7-methyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

5-(2-hydroksyetyl)-7-metyl-2-(4-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on, 5-(2-hydroxyethyl)-7-methyl-2-(4-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

5-(2-hydroksyetyl)-7-metyl-2-(3-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on, 5-(2-hydroxyethyl)-7-methyl-2-(3-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

5-(2-hydroksyetyl)-7-metyl-2-(2-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on, 5-(2-hydroxyethyl)-7-methyl-2-(2-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

5-(2-hydroksyetyl)-2-(4-metoksyfenyl)-7-metyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on, 5-(2-hydroxyethyl)-2-(4-methoxyphenyl)-7-methyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

5-(2-hydroksyetyl)-2-(4-hydroksyfenyl)-7-metyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on, 5-(2-hydroxyethyl)-2-(4-hydroxyphenyl)-7-methyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

2-(2-pyridyl)-5,7,7-trimetyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on, 2-(2-pyridyl)-5,7,7-trimethyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

5-etyl-7,7-dimetyl-2-(2-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on, 5-ethyl-7,7-dimethyl-2-(2-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

7,7-dimetyl-2-(4-hydroksyfenyl)-5-(2-metoksyetyl) -6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on, 7,7-dimethyl-2-(4-hydroxyphenyl)-5-(2-methoxyethyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

7,7-dimetyl-5-(2-hydroksyetyl)-2-(4-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on, 7,7-dimethyl-5-(2-hydroxyethyl)-2-(4-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

7,7-dimetyl-5(2-hydroksyetyl)-2-(3-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-fJbenzimidazol-6-on, 7,7-dimethyl-5(2-hydroxyethyl)-2-(3-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-fJbenzimidazol-6-one,

7,7-dimetyl-5-(2-hydroksyetyl)-2-(2-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on, 7,7-dimethyl-5-(2-hydroxyethyl)-2-(2-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

7,7-dimetyl-5-(2-hydroksyetyl)-2-(4-metoksyfenyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on, 7,7-dimethyl-5-(2-hydroxyethyl)-2-(4-methoxyphenyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

7,7-dimetyl-5-(2-hydroksyetyl)-2-(4-hydroksyfenyl) -6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on, 7,7-dimethyl-5-(2-hydroxyethyl)-2-(4-hydroxyphenyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

1,5-dimetyl-2-(4-pyridyl)-6,7-dihydro-lH,5H-pyrrolo[2,3-f]benzimidazol-6-on, 1,5-dimethyl-2-(4-pyridyl)-6,7-dihydro-1H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

1,5-dimetyl-2-(3-pyridyl)-6,7-dihydro-lH,5H-pyrrolo[2,3-f]benzimidazol-6-on, 1,5-dimethyl-2-(3-pyridyl)-6,7-dihydro-1H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

1,5-dimetyl-2-(2-pyridyl)-6,7-dihydro-lH,5H-pyrrolo[2,3-f]benzimidazol-6-on, 1,5-dimethyl-2-(2-pyridyl)-6,7-dihydro-1H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

1,5-dimetyl-2-(4-metoksyfenyl)-6,7-dihydro-lH,5H-pyrrolo[2,3-f]benzimidazol-6-on, 1,5-dimethyl-2-(4-methoxyphenyl)-6,7-dihydro-1H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

1,5-dimetyl-2-(4-hydroksyfenyl)-6,7-dihydro-lH,5H-pyrrolo[2,3-f]benzimidazol-6-on, 1,5-dimethyl-2-(4-hydroxyphenyl)-6,7-dihydro-1H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

5-etyl-l-metyl-2-(4-pyridyl)-6,7-dihydro-lH,5H-pyrrolo[2,3-f]benzimidazol-6-on, 5-ethyl-1-methyl-2-(4-pyridyl)-6,7-dihydro-1H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

5-etyl-l-metyl-2-(3-pyridyl)-6,7-dihydro-lH,5H-pyrrolo[2,3-f]benzimidazol-6-on, 5-ethyl-1-methyl-2-(3-pyridyl)-6,7-dihydro-1H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

5-etyl-l-metyl-2-(2-pyridyl)-6,7-dihydro-lH,5H-pyrrolo[2,3-f]benzimidazol-6-on, 5-ethyl-1-methyl-2-(2-pyridyl)-6,7-dihydro-1H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

5-etyl-2-(4-metoksyfenyl)-l-metyl-6,7-dihydro-lH,5H-pyrrolo[2,3-f]benzimidazol-6-on, 5-ethyl-2-(4-methoxyphenyl)-1-methyl-6,7-dihydro-1H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

5-etyl-2-(4-hydroksyfenyl)-l-metyl-6,7-dihydro-lH,5H-pyrrolo[2,3-f]benzimidazol-6-on, 5-ethyl-2-(4-hydroxyphenyl)-1-methyl-6,7-dihydro-1H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

5-(2-metoksyetyl)-l-metyl-2-(4-pyridyl)-6,7-dihydro-lH,5H-pyrrolo[2,3-f]benzimidazol-6-on, 5-(2-Methoxyethyl)-1-methyl-2-(4-pyridyl)-6,7-dihydro-1H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

5-(2-metoksyetyl)-l-metyl-2-(3-pyridyl)-6,7-dihydro-lH,5H-pyrrolo[2,3-f]benzimidazol-6-on, 5-(2-Methoxyethyl)-1-methyl-2-(3-pyridyl)-6,7-dihydro-1H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

5-(2-metoksyetyl)-l-metyl-2-(2-pyridyl)-6,7-dihydro-lH,5H-pyrrolo[2,3-f]benzimidazol-6-on, 5-(2-Methoxyethyl)-1-methyl-2-(2-pyridyl)-6,7-dihydro-1H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

5-(2-metoksyetyl)-2-(4-metoksyfenyl)-l-metyl-6,7-dihydro-lH,5H-pyrrolo[2,3-f]benzimidazol-6-on, 5-(2-methoxyethyl)-2-(4-methoxyphenyl)-1-methyl-6,7-dihydro-1H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

5-(2-metoksyetyl)-2-(4-hydroksyfenyl)-l-metyl-6,7-dihydro-1H,5H-pyrrolo[2,3-f]benzimidazol-6-on, 5-(2-Methoxyethyl)-2-(4-hydroxyphenyl)-1-methyl-6,7-dihydro-1H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

5-(2-hydroksyetyl)-l-metyl-2-(4-pyridyl)-6,7-dihydro-lH,5H-pyrrolo[2,3-f]benzimidazol-6-on, 5-(2-hydroxyethyl)-1-methyl-2-(4-pyridyl)-6,7-dihydro-1H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

5-(2-hydroksyetyl)-l-metyl-2-(3-pyridyl)-6,7-dihydro-lH,5H-pyrrolo[2,3-f]benzimidazol-6-on, 5-(2-Hydroxyethyl)-1-methyl-2-(3-pyridyl)-6,7-dihydro-1H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

5-(2-hydroksyetyl)-l-metyl-2-(2-pyridyl)-6,7-dihydro-lH,5H-pyrrolo[2,3-f]benzimidazol-6-on, 5-(2-hydroxyethyl)-1-methyl-2-(2-pyridyl)-6,7-dihydro-1H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

5-(2-hydroksyetyl)-2-(4-metoksyfenyl)-l-metyl-6,7-dihydro-lH,5H-pyrrolo[2,3-f]benzimidazol-6-on, 5-(2-hydroxyethyl)-2-(4-methoxyphenyl)-1-methyl-6,7-dihydro-1H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

5-(2-hydroksyetyl)-2-(4-hydroksyfenyl)-l-metyl-6,7-dihydro-lH,5H-pyrrolo[2,3-f]benzimidazol-6-on, 5-(2-hydroxyethyl)-2-(4-hydroxyphenyl)-1-methyl-6,7-dihydro-1H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

2-(4-pyridyl)-1,5,7-trimetyl-6,7-dihydro-lH,5H-pyrrolo[2,3-f]benzimidazol-6-on, 2-(4-pyridyl)-1,5,7-trimethyl-6,7-dihydro-1H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

2-(3-pyridyl)-1,5,7-trimetyl-6,7-dihydro-lH,5H-pyrrolo[2,3-f]benzimidazol-6-on, 2-(3-pyridyl)-1,5,7-trimethyl-6,7-dihydro-1H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

2-(2-pyridyl)-1,5,7-trimetyl-6,7-dihydro-lH,5H-pyrrolo[2,3-f]benzimidazol-6-on, 2-(2-pyridyl)-1,5,7-trimethyl-6,7-dihydro-1H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

2-(4-metoksyfenyl)-1,5,7-trimetyl-6,7-dihydro-lH,5H-pyrrolo[2,3-f]benzimidazol-6-on, 2-(4-Methoxyphenyl)-1,5,7-trimethyl-6,7-dihydro-1H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

2-(4-hydroksyfenyl)-1,5,7-trimetyl-6,7-dihydro-lH,5H-pyrrolo[2,3-f]benzimidazol-6-on, 2-(4-hydroxyphenyl)-1,5,7-trimethyl-6,7-dihydro-1H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

5-etyl-l,7-dimetyl-2-(4-pyridyl)-6,7-dihydro-lH,5H-pyrrolo[2,3-f]benzimidazol-6-on, 5-ethyl-1,7-dimethyl-2-(4-pyridyl)-6,7-dihydro-1H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

5-etyl-l,7-dimetyl-2-(3-pyridyl)-6,7-dihydro-lH,5H-pyrrolo[2,3-f]benzimidazol-6-on, 5-ethyl-1,7-dimethyl-2-(3-pyridyl)-6,7-dihydro-1H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

5-etyl-l,7-dimetyl-2-(2-pyridyl)-6,7-dihydro-lH,5H-pyrrolo[2,3-f]benzimidazol-6-on, 5-ethyl-1,7-dimethyl-2-(2-pyridyl)-6,7-dihydro-1H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

5-etyl-l,7-dimetyl-2-(4-metoksyfenyl)-6,7-dihydro-lH,5H-pyrrolo[2,3-f]benzimidazol-6-on, 5-ethyl-1,7-dimethyl-2-(4-methoxyphenyl)-6,7-dihydro-1H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

5-etyl-l,7-dimetyl-2-(4-hydroksyfenyl)-6,7-dihydro-lH,5H-pyrrolo[2,3-f]benzimidazol-6-on, 5-ethyl-1,7-dimethyl-2-(4-hydroxyphenyl)-6,7-dihydro-1H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

1,7-dimetyl-5-(2-metoksyetyl)-2-(4-pyridyl)-6,7-dihydro-lH,5H-pyrrolo[2,3-f]benzimidazol-6-on, 1,7-dimethyl-5-(2-methoxyethyl)-2-(4-pyridyl)-6,7-dihydro-1H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

1,7-dimetyl-5-(2-metoksyetyl)-2-(3-pyridyl)-6,7-dihydro-lH,5H-pyrrolo[2,3-f]benzimidazol-6-on, 1,7-dimethyl-5-(2-methoxyethyl)-2-(3-pyridyl)-6,7-dihydro-1H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

1,7-dimetyl-5-(2-metoksyetyl)-2-(2-pyridyl)-6,7-dihydro-lH,5H-pyrrolo[2,3-f]benzimidazol-6-on, 1,7-dimethyl-5-(2-methoxyethyl)-2-(2-pyridyl)-6,7-dihydro-1H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

1,7-dimetyl-5-(2-metoksyetyl)-2-(4-metoksyfenyl)-6,7-dihydro-1H,5H-pyrrolo[2,3-f]benzimidazol-6-on, 1,7-dimethyl-5-(2-methoxyethyl)-2-(4-methoxyphenyl)-6,7-dihydro-1H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

1,7-dimetyl-2-(4-hydroksyfenyl)-5-(2-metoksyetyl) -6,7-dihydro-1H,5H-pyrrolo[2,3-f]benzimidazol-6-on, 1,7-dimethyl-2-(4-hydroxyphenyl)-5-(2-methoxyethyl)-6,7-dihydro-1H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

1,7-dimetyl-5-(2-hydroksyetyl)-2-(4-pyridyl)-6,7-dihydro-lH,5H-pyrrolo[2,3-f]benzimidazol-6-on, 1,7-dimethyl-5-(2-hydroxyethyl)-2-(4-pyridyl)-6,7-dihydro-1H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

1,7-dimetyl-5-(2-hydroksyetyl)-2-(3-pyridyl)-6,7-dihydro-lH,5H-pyrrolo[2,3-f]benzimidazol-6-on, 1,7-dimethyl-5-(2-hydroxyethyl)-2-(3-pyridyl)-6,7-dihydro-1H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

1,7-dimetyl-5-(2-hydroksyetyl)-2-(2-pyridyl)-6,7-dihydro-lH,5H-pyrrolo[2,3-f]benzimidazol-6-on, 1,7-dimethyl-5-(2-hydroxyethyl)-2-(2-pyridyl)-6,7-dihydro-1H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

1,7-dimetyl-5-(2-hydroksyetyl)-2-(4-metoksyfenyl)-6,7-dihydro-1H,5H-pyrrolo[2,3-f]benzimidazol-6-on, 1,7-dimethyl-5-(2-hydroxyethyl)-2-(4-methoxyphenyl)-6,7-dihydro-1H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

1,7-dimetyl-5-(2-hydroksyetyl)-2-(4-hydroksyfenyl)-6,7-dihydro-1H,5H-pyrrolo[2,3-f]benzimidazol-6-on, 1,7-dimethyl-5-(2-hydroxyethyl)-2-(4-hydroxyphenyl)-6,7-dihydro-1H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

2-(3-pyridyl)-1,5,7,7-tetrametyl-6,7-dihydro-lH,5H-pyrrolo[2,3-f]benzimidazol-6-on, 2-(3-pyridyl)-1,5,7,7-tetramethyl-6,7-dihydro-1H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

2-(2-pyridyl)-1,5,7,7-tetrametyl-6,7-dihydro-lH,5H-pyrrolo[2,3-f]benzimidazol-6-on, 2-(2-pyridyl)-1,5,7,7-tetramethyl-6,7-dihydro-1H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

2-(4-metoksyfenyl)-1,5,7,7-tetrametyl-6,7-dihydro-lH,5H-pyrrolo[2,3-f]benzimidazol-6-on, 2-(4-Methoxyphenyl)-1,5,7,7-tetramethyl-6,7-dihydro-1H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

2-(4-hydroksyfenyl)-1,5,7,7-tetrametyl-6,7-dihydro-lH,5H-pyrrolo[2,3-f]benzimidazol-6-on, 2-(4-hydroxyphenyl)-1,5,7,7-tetramethyl-6,7-dihydro-1H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

5-etyl-2-(4-pyridyl)-1,7,7-trimetyl-6,7-dihydro-lH,5H-pyrrolo-[2,3-f]benzimidazol-6-on, 5-ethyl-2-(4-pyridyl)-1,7,7-trimethyl-6,7-dihydro-1H,5H-pyrrolo-[2,3-f]benzimidazol-6-one,

5-etyl-2-(3-pyridyl)-1,7,7-trimetyl-6,7-dihydro-lH,5H-pyrrolo-[2,3-f]benzimidazol-6-on, 5-ethyl-2-(3-pyridyl)-1,7,7-trimethyl-6,7-dihydro-1H,5H-pyrrolo-[2,3-f]benzimidazol-6-one,

5-etyl-2-(2-pyridyl)-1,7,7-trimetyl-6,7-dihydro-lH,5H-pyrrolo-[2,3-f]benzimidazol-6-on, 5-ethyl-2-(2-pyridyl)-1,7,7-trimethyl-6,7-dihydro-1H,5H-pyrrolo-[2,3-f]benzimidazol-6-one,

5-etyl-2-(4-metoksyfenyl)-l,7,7-trimetyl-6,7-dihydro-lH,5H-pyrrolo[2,3-f]benzimidazol-6-on, 5-ethyl-2-(4-methoxyphenyl)-1,7,7-trimethyl-6,7-dihydro-1H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

5-etyl-2-(4-hydroksyfenyl)-1,7,7-trimetyl-6,7-dihydro-lH,5H-pyrrolo[2,3-f]benzimidazol-6-on, 5-ethyl-2-(4-hydroxyphenyl)-1,7,7-trimethyl-6,7-dihydro-1H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

5-(2-metoksyetyl)-2-(4-pyridyl)-1,7,7-trimetyl-6,7-dihydro-lH,5H-pyrrolo[2,3-f]benzimidazol-6-on, 5-(2-Methoxyethyl)-2-(4-pyridyl)-1,7,7-trimethyl-6,7-dihydro-1H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

5-(2-metoksyetyl)-2-(3-pyridyl)-1,7,7-trimetyl-6,7-dihydro-lH,5H-pyrrolo[2,3-f]benzimidazol-6-on, 5-(2-Methoxyethyl)-2-(3-pyridyl)-1,7,7-trimethyl-6,7-dihydro-1H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

5-(2-metoksyetyl)-2-(2-pyridyl)-1,7,7-trimetyl-6,7-dihydro-lH,5H-pyrrolo[2,3-f]benzimidazol-6-on, 5-(2-Methoxyethyl)-2-(2-pyridyl)-1,7,7-trimethyl-6,7-dihydro-1H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

5-(2-metoksyetyl)-2-(4-metoksyfenyl)-1,7,7-trimetyl-6,7-dihydro-lH,5H-pyrrolo[2,3-f]benzimidazol-6-on, 5-(2-methoxyethyl)-2-(4-methoxyphenyl)-1,7,7-trimethyl-6,7-dihydro-1H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

5-(2-metoksyetyl)-2-(4-hydroksyfenyl)-1,7,7-trimetyl-6,7-dihydro-lH,5H-pyrrolo[2,3-f]benzimidazol-6-on, 5-(2-methoxyethyl)-2-(4-hydroxyphenyl)-1,7,7-trimethyl-6,7-dihydro-1H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

5-(2-hydroksyetyl)-2-(4-pyridyl)-1,7,7-trimetyl-6,7-dihydro-1H,5H-pyrrolo[2,3-f]benzimidazol-6-on, 5-(2-hydroxyethyl)-2-(4-pyridyl)-1,7,7-trimethyl-6,7-dihydro-1H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

5-(2-hydroksyetyl)-2-(3-pyridyl)-1,7,7-trimetyl-6,7-dihydro-1H,5H-pyrrolo[2,3-f]benzimidazol-6-on, 5-(2-hydroxyethyl)-2-(3-pyridyl)-1,7,7-trimethyl-6,7-dihydro-1H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

5-(2-hydroksyetyl)-2-(2-pyridyl)-1,7,7-trimetyl-6,7-dihydro-1H,5H-pyrrolo[2,3-f]benzimidazol-6-on, 5-(2-hydroxyethyl)-2-(2-pyridyl)-1,7,7-trimethyl-6,7-dihydro-1H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

5-(2-hydroksyetyl)-2-(4-metoksyfenyl)-1,7,7-trimetyl-6,7-dihydro-lH,5H-pyrrolo[2,3-f]benzimidazol-6-on, 5-(2-hydroxyethyl)-2-(4-methoxyphenyl)-1,7,7-trimethyl-6,7-dihydro-1H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

5-(2-hydroksyetyl)-2-(4-hydroksyfenyl)-1,7,7-trimetyl-6,7-dihydro-lH,5H-pyrrolo[2,3-f]benzimidazol-6-on, 5-(2-hydroxyethyl)-2-(4-hydroxyphenyl)-1,7,7-trimethyl-6,7-dihydro-1H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

3,5-dimetyl-2-(4-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on, 3,5-dimethyl-2-(4-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

3,5-dimetyl-2-(3-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benz-imidazol-6-on, 3,5-dimethyl-2-(3-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benz-imidazol-6-one,

3,5-dimetyl-2-(2-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-fjbenz-imidazol-6-on, 3,5-Dimethyl-2-(2-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-fjbenz-imidazol-6-one,

3,5-dimetyl-2-(4-metoksyfenyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on, 3,5-dimethyl-2-(4-methoxyphenyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

3,5-dimetyl-2-(4-hydroksyfenyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on, 3,5-dimethyl-2-(4-hydroxyphenyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

5-etyl-3-metyl-2-(4-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on, 5-ethyl-3-methyl-2-(4-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

5-etyl-3-metyl-2-(3-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on, 5-ethyl-3-methyl-2-(3-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

5-etyl-3-metyl-2-(2-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on, 5-ethyl-3-methyl-2-(2-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

5-etyl-2-(4-metoksyfenyl)-3-metyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on, 5-ethyl-2-(4-methoxyphenyl)-3-methyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

5-etyl-2-(4-hydroksyfenyl)-3-metyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on, 5-ethyl-2-(4-hydroxyphenyl)-3-methyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

5-(2-metoksyetyl)-3-metyl-2-(4-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on, 5-(2-Methoxyethyl)-3-methyl-2-(4-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

5-(2-metoksyetyl)-3-metyl-2-(3-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on, 5-(2-Methoxyethyl)-3-methyl-2-(3-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

5-(2-metoksyetyl)-3-metyl-2-(2-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on, 5-(2-Methoxyethyl)-3-methyl-2-(2-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

5-(2-metoksyetyl)-2-(4-metoksyfenyl)-3-metyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on, 5-(2-methoxyethyl)-2-(4-methoxyphenyl)-3-methyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

2-(4-hydroksyfenyl)-5-(2-metoksyetyl)-3-metyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on, 2-(4-hydroxyphenyl)-5-(2-methoxyethyl)-3-methyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

5-(2-hydroksyetyl)-3-metyl-2-(4-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on, 5-(2-hydroxyethyl)-3-methyl-2-(4-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

5-(2-hydroksyetyl)-3-metyl-2-(3-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on, 5-(2-hydroxyethyl)-3-methyl-2-(3-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

5-(2-hydroksyetyl)-3-metyl-2-(2-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on, 5-(2-hydroxyethyl)-3-methyl-2-(2-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

5-(2-hydroksyetyl)-2-(4-metoksyfenyl)-3-metyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on, 5-(2-hydroxyethyl)-2-(4-methoxyphenyl)-3-methyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

5-(2-hydroksyetyl)-2-(4-hydroksyfenyl)-3-metyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on, 5-(2-hydroxyethyl)-2-(4-hydroxyphenyl)-3-methyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

2-(4-pyridyl)-3,5,7-trimetyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on, 2-(4-pyridyl)-3,5,7-trimethyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

2-(3-pyridyl)-3,5,7-trimetyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on, 2-(3-pyridyl)-3,5,7-trimethyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

2-(2-pyridyl)-3,5,7-trimetyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on, 2-(2-pyridyl)-3,5,7-trimethyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

2-(4-metoksyfenyl)-3,5,7-trimetyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on, 2-(4-Methoxyphenyl)-3,5,7-trimethyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

2-(4-hydroksyfenyl)-3,5,7-trimetyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on, 2-(4-hydroxyphenyl)-3,5,7-trimethyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

5-etyl-3,7-dimetyl-2-(4-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on, 5-ethyl-3,7-dimethyl-2-(4-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

5-etyl-3,7-dimetyl-2-(3-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on, 5-ethyl-3,7-dimethyl-2-(3-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

5-etyl-3,7-dimetyl-2-(2-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on, 5-ethyl-3,7-dimethyl-2-(2-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

5-etyl-3,7-dimetyl-2-(4-metoksyfenyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on, 5-ethyl-3,7-dimethyl-2-(4-methoxyphenyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

5-etyl-3,7-dimetyl-2-(4-hydroksyfenyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on, 5-ethyl-3,7-dimethyl-2-(4-hydroxyphenyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

3,7-dimetyl-5-(2-metoksyetyl)-2-(4-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on, 3,7-dimethyl-5-(2-methoxyethyl)-2-(4-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

3,7-dimetyl-5-(2-metoksyetyl)-2-(3-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on, 3,7-dimethyl-5-(2-methoxyethyl)-2-(3-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

3,7-dimetyl-5-(2-metoksyetyl)-2-(2-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on, 3,7-dimethyl-5-(2-methoxyethyl)-2-(2-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

3,7-dimetyl-5-(2-metoksyetyl)-2-(4-metoksyfenyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on, 3,7-dimethyl-5-(2-methoxyethyl)-2-(4-methoxyphenyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

3,7-dimetyl-2-(4-hydroksyfenyl)-5-(2-metoksyetyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on, 3,7-dimethyl-2-(4-hydroxyphenyl)-5-(2-methoxyethyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

3,7-dimetyl-5-(2-hydroksyetyl)-2-(4-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on, 3,7-dimethyl-5-(2-hydroxyethyl)-2-(4-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

3,7-dimetyl-5-(2-hydroksyetyl)-2-(3-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on, 3,7-dimethyl-5-(2-hydroxyethyl)-2-(3-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

3,7-dimetyl-5-(2-hydroksyetyl)-2-(2-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on, 3,7-dimethyl-5-(2-hydroxyethyl)-2-(2-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

3,7-dimetyl-5-(2-hydroksyetyl)-2-(4-metoksyfenyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on, 3,7-dimethyl-5-(2-hydroxyethyl)-2-(4-methoxyphenyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

3,7-dimetyl-5-(2-hydroksyetyl)-2-(4-hydroksyfenyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on, 3,7-dimethyl-5-(2-hydroxyethyl)-2-(4-hydroxyphenyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

2-(3-pyridyl)-3,5,7,7-tetrametyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on, 2-(3-pyridyl)-3,5,7,7-tetramethyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

2-(2-pyridyl)-3,5,7,7-tetrametyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on, 2-(2-pyridyl)-3,5,7,7-tetramethyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

2-(4-metoksyfenyl)-3,5,7,7-tetrametyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on, 2-(4-methoxyphenyl)-3,5,7,7-tetramethyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

2-(4-hydroksyfenyl)-3,5,7,7-tetrametyl-6,7-dihydro-3H,5H-pyrrolo-[2,3-f]benzimidazol-6-on, 2-(4-hydroxyphenyl)-3,5,7,7-tetramethyl-6,7-dihydro-3H,5H-pyrrolo-[2,3-f]benzimidazol-6-one,

5-etyl-2-(4-pyridyl)-3,7,7-trimetyl-6,7-dihydro-3H,5H-pyrrolo-[2,3-f]benzimidazol-6-on, 5-ethyl-2-(4-pyridyl)-3,7,7-trimethyl-6,7-dihydro-3H,5H-pyrrolo-[2,3-f]benzimidazol-6-one,

5-etyl-2-(3-pyridyl)-3,7,7-trimetyl-6,7-dihydro-3H,5H-pyrrolo-[2,3-f]benzimidazol-6-on, 5-ethyl-2-(3-pyridyl)-3,7,7-trimethyl-6,7-dihydro-3H,5H-pyrrolo-[2,3-f]benzimidazol-6-one,

5-etyl-2-(2-pyridyl)-3,7,7-trimetyl-6,7-dihydro-3H,5H-pyrrolo-[2,3-f]benzimidazol-6-on, 5-ethyl-2-(2-pyridyl)-3,7,7-trimethyl-6,7-dihydro-3H,5H-pyrrolo-[2,3-f]benzimidazol-6-one,

5-etyl-2-(4-metoksyfenyl)-3,7,7-trimetyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on, 5-ethyl-2-(4-methoxyphenyl)-3,7,7-trimethyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

5-etyl-2-(4-hydroksyfenyl)-3,7,7-trimetyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on, 5-ethyl-2-(4-hydroxyphenyl)-3,7,7-trimethyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

5-(2-metoksyetyl)-2-(4-pyridyl)-3,7,7-trimetyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on, 5-(2-Methoxyethyl)-2-(4-pyridyl)-3,7,7-trimethyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

5-(2-metoksyetyl)-2-(3-pyridyl)-3,7,7-trimetyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on, 5-(2-Methoxyethyl)-2-(3-pyridyl)-3,7,7-trimethyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

5-(2-metoksyetyl)-2-(2-pyridyl)-3,7,7-trimetyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on, 5-(2-Methoxyethyl)-2-(2-pyridyl)-3,7,7-trimethyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

5-(2-metoksyetyl)-2-(4-metoksyfenyl)-3,7,7-trimetyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on, 5-(2-methoxyethyl)-2-(4-methoxyphenyl)-3,7,7-trimethyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

2-(4-hydroksyfenyl)-5-(2-metoksyetyl)-3,7,7-trimetyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on, 2-(4-hydroxyphenyl)-5-(2-methoxyethyl)-3,7,7-trimethyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

5-(2-hydroksyetyl)-2-(4-pyridyl)-3,7,7-trimetyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on, 5-(2-hydroxyethyl)-2-(4-pyridyl)-3,7,7-trimethyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

5-(2-hydroksyetyl)-2-(3-pyridyl)-3,7,7-trimetyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on, 5-(2-hydroxyethyl)-2-(3-pyridyl)-3,7,7-trimethyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

5-(2-hydroksyetyl)-2-(2-pyridyl)-3,7,7-trimetyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on, 5-(2-Hydroxyethyl)-2-(2-pyridyl)-3,7,7-trimethyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

5-(2-hydroksyetyl)-2-(4-metoksyfenyl)-3,7,7-trimetyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on, 5-(2-hydroxyethyl)-2-(4-methoxyphenyl)-3,7,7-trimethyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

5-(2-hydroksyetyl)-2-(4-hydroksyfenyl)-3,7,7-trimetyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on, 5-(2-hydroxyethyl)-2-(4-hydroxyphenyl)-3,7,7-trimethyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

5-benzyl-7,7-dimetyl-2-(3-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on, 5-benzyl-7,7-dimethyl-2-(3-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

5-benzyl-7,7-dimetyl-2-(2-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on og 5-benzyl-7,7-dimethyl-2-(2-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one and

5-benzyl-7,7-dimetyl-2-(4-hydroksyfenyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on, deres 3H-tautomerer og deres syreaddisjonssalter. 5-Benzyl-7,7-dimethyl-2-(4-hydroxyphenyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one, their 3H-tautomers and their acid addition salts.

Foretrukne forbindelser med den ovenfor angitte formel I er imidlertid de forbindelser hvor R1utgjør et hydrogenatom, spesielt forbindelser med formel I, hvori However, preferred compounds of the above-mentioned formula I are those compounds where R1 constitutes a hydrogen atom, especially compounds of formula I, in which

R1er et hydrogenatom,R1 is a hydrogen atom,

R2er et hydrogenatom, en alkylgruppe med 1-3 karbonatomer, en eventuelt med en fenyl-, pyridyl- eller tienylgruppe substituert alkylgruppe med 1 eller 2 karbonatomer i alkyldelen, en vinylengruppe som terminalt er substituert med en fenyl- eller pyridylgruppe, en eventuelt med en metyl-, amino-, metylamino-, dimetylamino- eller morfolinogruppe substituert pyridylgruppe, en med 2 halogenatomer eller med 1 halogenatom og 1 morfolinogruppe substituert pyridylgruppe, en eventuelt med en metylgruppe substituert furyl-, tienyl-, pyrrolyl-, oksazolyl-, pyrimidinyl-, pyrazinyl-, pyridazinyl-, kinolyl- eller akridinylgruppe, en med en fenylgruppe eller med 1 halogenatom og 1 metoksy- eller trifluormetylgruppe substituert kinolylgruppe, en piperidinyl- eller 1,2,3,4-tetrahydro-kinolylgruppe eller en 5,6,7,8-tetrahydrokinolylgruppe som eventuelt på N-atomet er substituert med en acetygruppe, en eventuelt med et halogenatom, en hydroksy-, metoksy-, metylmerkapto-, metylsulfinyl-, metyl-sulf onyl-, nitro-, amino-, metylamino-, dimetylamino-, acetyl-amino- eller cyanogruppe substituert fenylgruppe, en eventuelt med et halogenatom, en metoksy-, metylmerkapto-, metylsulfinyl-eller metylsulfonylgruppe disubstituert fenylgruppe, hvor substituentene kan være like eller forskjellige, en hydroksy-di-tert-butylfenyl- eller amino-dihalogenfenylgruppe, R2 is a hydrogen atom, an alkyl group with 1-3 carbon atoms, an optionally substituted with a phenyl, pyridyl or thienyl group alkyl group with 1 or 2 carbon atoms in the alkyl part, a vinylene group which is terminally substituted with a phenyl or pyridyl group, an optionally with a methyl-, amino-, methylamino-, dimethylamino- or morpholino-substituted pyridyl group, a pyridyl group substituted with 2 halogen atoms or with 1 halogen atom and 1 morpholino group, a furyl-, thienyl-, pyrrolyl-, oxazolyl-, pyrimidinyl- optionally substituted with a methyl group , pyrazinyl, pyridazinyl, quinolyl or acridinyl group, a quinolyl group substituted with a phenyl group or with 1 halogen atom and 1 methoxy or trifluoromethyl group, a piperidinyl or 1,2,3,4-tetrahydro-quinolyl group or a 5,6, 7,8-tetrahydroquinolyl group which is optionally substituted on the N-atom with an acetyl group, one optionally with a halogen atom, a hydroxy-, methoxy-, methylmercapto-, methylsulfinyl-, methylsulfonyl-, nitro-, amino-, methylamino-, dimethylamino-, acetyl-amino- or cyano group substituted phenyl group, an optionally with a halogen atom, a methoxy-, methylmercapto-, methylsulfinyl or methylsulfonyl group disubstituted phenyl group, where the substituents can be the same or different, a hydroxy-di-tert-butylphenyl or amino-dihalophenyl group,

R3er en alkylgruppe med 1-5 karbonatomer, en benzyl-, 2-hydroksyetyl- eller 2-metoksyetylgruppe, R3 is an alkyl group with 1-5 carbon atoms, a benzyl, 2-hydroxyethyl or 2-methoxyethyl group,

R4og R5, som kan være like eller forskjellige, betyr hydrogenatomer eller metylgrupper, deres 3H-tautomerer og deres syreaddisjonssalter. R 4 and R 5 , which may be the same or different, mean hydrogen atoms or methyl groups, their 3 H tautomers and their acid addition salts.

Særlig foretrukne forbindelser med formel I er imidlertid forbindelser hvor However, particularly preferred compounds of formula I are compounds where

R1er et hydrogenatom,R1 is a hydrogen atom,

R2er en med en cyano-, dimetylamino-, metoksy-, metylmerkapto-, metylsulfinyl- eller metylsulfonylgruppe substituert fenylgruppe, en eventuelt med metyl-, amino-, metylamino-, dimetylamino-eller morfolinogruppe substituert pyridylgruppe, en med 2 halogenatomer eller med 1 halogenatom og 1 morfolinogruppe substituert pyridylgruppe, en eventuelt med en metylgruppe substituert furyl-, tienyl-, pyrrolyl-, oksazolyl-, pyrimidinyl-, pyrazinyl-, pyridazinyl-, kinolyl- eller akridinylgruppe, R2 is a phenyl group substituted with a cyano, dimethylamino, methoxy, methylmercapto, methylsulfinyl or methylsulfonyl group, a pyridyl group optionally substituted with a methyl, amino, methylamino, dimethylamino or morpholino group, one with 2 halogen atoms or with 1 halogen atom and 1 morpholino group substituted pyridyl group, a furyl, thienyl, pyrrolyl, oxazolyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolyl or acridinyl group optionally substituted with a methyl group,

R3er en alkylgruppe med 1-5 karbonatomer,R3 is an alkyl group with 1-5 carbon atoms,

R4er et hydrogenatom eller en metylgruppe ogR4 is a hydrogen atom or a methyl group and

R5er en metylgruppe, spesielt slike hvoriR5 is a methyl group, especially those in which

Rx er et hydrogenatom,Rx is a hydrogen atom,

R2er en fenylgruppe som i 4-stilling er substituert med en cyano-, dimetylamino-, metylsulfinyl- eller metylsulfonylgruppe, en furyl-2-, tienyl-2-, pyridyl-, 4-pyrimidinyl- eller 4-metyloksazol-5-ylgruppe, R2 is a phenyl group which is substituted in the 4-position with a cyano-, dimethylamino-, methylsulfinyl or methylsulfonyl group, a furyl-2-, thienyl-2-, pyridyl-, 4-pyrimidinyl- or 4-methyloxazol-5-yl group,

R3er en alkylgruppe med 1-3 karbonatomer,R3 is an alkyl group with 1-3 carbon atoms,

R4og R5hver betyr en metylgruppe, deres 3H-tautomerer ogR4 and R5 each mean a methyl group, their 3H-tautomers and

deres syreaddisjonssalter.their acid addition salts.

I henhold til oppfinnelsen oppnås de nye forbindelsene etter følgende fremgangsmåter: According to the invention, the new compounds are obtained by the following methods:

a) Cyklisering av en forbindelse med formela) Cyclization of a compound of formula

hvor where

R3og R5er som innledningsvis definert,R3 and R5 are as initially defined,

én av restene h1eller B1betyr en RjNH-gruppe, hvor Rx er som innledningsvis definert, og den andre av restene A1eller B1betyr en one of the residues h1 or B1 means an RjNH group, where Rx is as initially defined, and the other of the residues A1 or B1 means a

NR6-gruppe, hvor NR6 group, where

R2er som innledningsvis definert ogR2 is as initially defined and

R6er et hydrogenatom eller, dersom R1utgjør et hydrogenatom,R6 is a hydrogen atom or, if R1 is a hydrogen atom,

en eventuelt med en fenylgruppe substituert alkylgruppe med 1-3 karbonatomer, an optionally substituted by a phenyl group alkyl group with 1-3 carbon atoms,

Z1og Z2, som kan være like eller forskjellige, betyr nukleofile utgående grupper, som eventuelt substituerte amino-, alkoksy-, fenylalkoksy-, fenoksy-, alkylmerkapto-, fenylalkylmerkapto-eller fenyltiogrupper, eller Z 1 and Z 2 , which may be the same or different, mean nucleophilic leaving groups, such as optionally substituted amino, alkoxy, phenyl alkoxy, phenoxy, alkyl mercapto, phenyl alkyl mercapto or phenylthio groups, or

Zlog Z2sammen betyr et oksygen- eller svovelatom, en imino-gruppe som eventuelt er substituert med en alkyl- eller fenylalkylgruppe, hvor de ovenfor nevnte alkyldeler kan inneholde 1-3 karbonatomer, eller en alkylendioksygruppe med 2 eller 3 karbonatomer. Zlog Z2 together means an oxygen or sulfur atom, an imino group which is optionally substituted with an alkyl or phenylalkyl group, where the above-mentioned alkyl parts may contain 1-3 carbon atoms, or an alkylenedioxy group with 2 or 3 carbon atoms.

Aktuelle grupper for Zx og Z2er eksempelvis metoksy-, etoksy-, propoksy-, benzyloksy-, metylmerkapto-, etylmerkapto-, propylmerkapto-, fenylmerkapto- eller benzylmerkaptogruppen eller Relevant groups for Zx and Z2 are, for example, the methoxy, ethoxy, propoxy, benzyloxy, methyl mercapto, ethyl mercapto, propyl mercapto, phenyl mercapto or benzyl mercapto group or

for Zx og Z2sammen med karbonatomet, eksempelvis en karbonyl-eller tiokarbonylgruppe. for Zx and Z2 together with the carbon atom, for example a carbonyl or thiocarbonyl group.

Omsetningen skjer hensiktsmessig i et oppløsningsmiddel eller i en oppløsningsmiddelblanding som etanol, isopropanol, iseddik, tetrahydrofuran, dioksan, benzen, toluen, xylen, klorbenzen, glykol, glykol-monometyleter, glykol-dimetyleter, dietylenglykoldimetyleter, dimetylformamid, tetralin eller sulfolan, eventuelt i nærvær av et kondensasjonsmiddel, som fosforoksyklorid, tionylklorid, sulfurylklorid, saltsyre, svovelsyre, fosforsyre, polyfosforsyre, p-toluensulfonsyre, iseddik, eddiksyreanhydrid, N,N'-dicykloheksyl-karbodiimid, karbonyldiimidazol, kaliummetylat eller kalium-tert-butylat, ved temperaturer mellom 0 og 300°C, fortrinnsvis ved reaksjonsblandingens kokepunkt, f.eks. ved temperaturer mellom 50 og 285°C. Omsetningen kan imidlertid også foretas i smelter. The reaction conveniently takes place in a solvent or in a solvent mixture such as ethanol, isopropanol, glacial acetic acid, tetrahydrofuran, dioxane, benzene, toluene, xylene, chlorobenzene, glycol, glycol monomethyl ether, glycol dimethyl ether, diethylene glycol dimethyl ether, dimethylformamide, tetralin or sulfolane, possibly in the presence of a condensing agent, such as phosphorus oxychloride, thionyl chloride, sulfuryl chloride, hydrochloric acid, sulfuric acid, phosphoric acid, polyphosphoric acid, p-toluenesulfonic acid, glacial acetic acid, acetic anhydride, N,N'-dicyclohexylcarbodiimide, carbonyldiimidazole, potassium methylate or potassium tert-butylate, at temperatures between 0 and 300°C, preferably at the boiling point of the reaction mixture, e.g. at temperatures between 50 and 285°C. However, turnover can also be carried out in smelters.

Det er imidlertid særlig fordelaktig å foreta omsetningen på en slik måte at en av utgangsforbindelsene med formel II fremstilles i reaksjonsblandingen, enten ved reduksjon av en tilsvarende nitroforbindelse, f.eks. ved reduksjon med hydrogen i nærvær av en hydreringskatalysator However, it is particularly advantageous to carry out the reaction in such a way that one of the starting compounds of formula II is produced in the reaction mixture, either by reduction of a corresponding nitro compound, e.g. by reduction with hydrogen in the presence of a hydrogenation catalyst

eller ved omsetning av en tilsvarende diaminoforbindelse med et overskudd av det anvendte acyleringsmiddel, f.eks. med et overskudd av det tilsvarende nitril, anhydrid, ester, tioester, ortoester, amid, tioamid, halogenid eller metoksyjodid. or by reacting a corresponding diamino compound with an excess of the acylating agent used, e.g. with an excess of the corresponding nitrile, anhydride, ester, thioester, orthoester, amide, thioamide, halide or methoxyiodide.

Reduksjonen av en nitrogruppe foretas herunder fortrinnsvis i et egnet oppløsningsmiddel som iseddik, vann, etanol eller vann/iseddik, hensiktsmessig med nascerende hydrogen, f.eks. i nærvær av sink/iseddik, tinn/saltsyre eller tinn(II)klorid/saltsyre eller med katalytisk aktivert hydrogen, f.eks. med hydrogen i nærvær av platina, palladium eller Raney-nikkel, ved temperaturer mellom 0 og 150°C, fortrinnsvis ved temperaturer mellom 20 og 125°C, mens The reduction of a nitro group is preferably carried out in a suitable solvent such as glacial acetic acid, water, ethanol or water/glacial acetic acid, suitably with nascent hydrogen, e.g. in the presence of zinc/glacial acetic acid, tin/hydrochloric acid or tin(II) chloride/hydrochloric acid or with catalytically activated hydrogen, e.g. with hydrogen in the presence of platinum, palladium or Raney nickel, at temperatures between 0 and 150°C, preferably at temperatures between 20 and 125°C, while

acyleringen hensiktsmessig foretas i et oppløsningsmiddel som metylenklorid, kloroform, tetraklormetan, eter, tetrahydrofuran, dioksan, benzen, toluen, acetonitril eller dimetylformamid, eventuelt i nærvær av et middel som aktiverer syren eller i nærvær av et vanntiltrekkende middel, f.eks. i nærvær av klormaursyreetylester, tionylklorid, fosfortriklorid, fosfor-pentoksyd, N,N-dicykloheksylkarbodiimid, N,N-dicykloheksyl-karbodiimid/N-hydroksysuccinimid, N,N'-karbonyldiimidazol eller N,N'-tionyldiimidazol eller trifenylfosfin/tetraklormetan, eller i nærvær av et middel som aktiverer amiogruppen, f.eks. fosfortriklorid, og eventuelt i nærvær av en uorganisk base som natriumkarbonat, eller en tertiær organisk base som trietylamin eller pyridin, som samtidig kan tjene som oppløsningsmiddel, ved temperaturer mellom -25 og 250°C, fortrinnsvis ved temperaturer mellom -10°C og kokepunktet for det anvendte oppløsnings- the acylation is conveniently carried out in a solvent such as methylene chloride, chloroform, tetrachloromethane, ether, tetrahydrofuran, dioxane, benzene, toluene, acetonitrile or dimethylformamide, optionally in the presence of an agent that activates the acid or in the presence of a water-attracting agent, e.g. in the presence of chloroformate ethyl ester, thionyl chloride, phosphorus trichloride, phosphorus pentoxide, N,N-dicyclohexylcarbodiimide, N,N-dicyclohexylcarbodiimide/N-hydroxysuccinimide, N,N'-carbonyldiimidazole or N,N'-thionyldiimidazole or triphenylphosphine/tetrachloromethane, or in the presence of an agent that activates the amio group, e.g. phosphorus trichloride, and optionally in the presence of an inorganic base such as sodium carbonate, or a tertiary organic base such as triethylamine or pyridine, which can simultaneously serve as a solvent, at temperatures between -25 and 250°C, preferably at temperatures between -10°C and the boiling point for the resolution used

middel. Omsetningen kan også utføres uten oppløsningsmiddel. Vann som oppstår under omsetningen kan dessuten fraskilles ved azeotrop destillasjon, f.eks. ved oppvarming med toluen med påsatt vannfelle, eller ved tilsetning av et tørkemiddel som magnesiumsulfat eller molekylarsikt. medium. The reaction can also be carried out without a solvent. Water that occurs during the reaction can also be separated by azeotropic distillation, e.g. by heating with toluene with an attached water trap, or by adding a drying agent such as magnesium sulphate or molecular sieve.

Under reduksjonen kan forekommende dobbeltbindinger i resten R2med-reduseres. Under acyleringen i nærvær av et halogenholdig kondensasjonsmiddel som fosforoksyklorid, kan dessuten forekommende hydroksygrupper erstattes med halogenatomer . During the reduction, double bonds occurring in the residue R2 can be reduced. During the acylation in the presence of a halogen-containing condensing agent such as phosphorus oxychloride, the hydroxy groups present can also be replaced by halogen atoms.

b) Omsetning av en forbindelse med formelb) Reaction of a compound with formula

hvor where

R3, R4og R5er som innledningsvis definert,R3, R4 and R5 are as initially defined,

en av restene A2eller B2betyr en RiNH-gruppe, hvor R: er som innledningsvis definert, og one of the residues A2 or B2 means a RiNH group, where R: is as initially defined, and

den andre av restene A2eller B2er en NH2-gruppe, med et aldehyd med formel the other of the residues A2 or B2 is an NH2 group, with an aldehyde of formula

hvor where

R2er som innledningsvis definert, etterfulgt av oksydasjon. R2 is as initially defined, followed by oxidation.

Omsetningen foretas hensiktsmessig i et egnet oppløsnings-middel som metanol, etanol, iseddik eller etylenklorid, ved temperaturer mellom 20 og 100°C. Den påfølgende oksydasjon foretas med et oksydasjonsmiddel som oksygen, hydrogenperoksyd eller en persyre som m-klorperbenzosyre, ved temperaturer mellom 20 og 100°C, fortrinnsvis ved temperaturer mellom 40 og 80°C. The reaction is conveniently carried out in a suitable solvent such as methanol, ethanol, glacial acetic acid or ethylene chloride, at temperatures between 20 and 100°C. The subsequent oxidation is carried out with an oxidizing agent such as oxygen, hydrogen peroxide or a peracid such as m-chloroperbenzoic acid, at temperatures between 20 and 100°C, preferably at temperatures between 40 and 80°C.

Oppnår man i henhold til oppfinnelsen, en forbindelse med formel I, hvor R1utgjør et hydrogenatom og/eller R2inneholder en hydroksy- eller merkaptogruppe, kan disse ved alkylering overføres i den tilsvarende alkylforbindelse, og/eller dersom en forbindelse med formel I, hvor R2inneholder en aminogruppe, så kan denne ved alkanoylering overføres i den tilsvarende alkanoylforbindelse, og/eller If, according to the invention, a compound of formula I is obtained, where R1 constitutes a hydrogen atom and/or R2 contains a hydroxy or mercapto group, these can be transferred by alkylation into the corresponding alkyl compound, and/or if a compound of formula I, where R2 contains a amino group, then this can be transferred by alkanoylation in the corresponding alkanoyl compound, and/or

en forbindelse med formel I, hvor R2utgjør en vinylengruppe som terminalt er substituert med en fenyl- eller pyridylgruppe, kan denne ved katalytisk hydrering overføres i en tilsvarende forbindelse med formel I, hvor R2utgjør en etylengruppe som terminalt er substituert med en fenyl- eller pyridylgruppe, og/eller a compound of formula I, where R2 is a vinylene group that is terminally substituted with a phenyl or pyridyl group, this can be transferred by catalytic hydrogenation into a corresponding compound of formula I, where R2 is an ethylene group that is terminally substituted with a phenyl or pyridyl group, and or

en forbindelse med formel I, hvor R1utgjør en benzylgruppe,a compound of formula I, where R1 constitutes a benzyl group,

kan denne ved katalytisk hydrering overføres i en tilsvarende forbindelse med formel I, hvor Rx utgjør et hydrogenatom, og/eller can this be transferred by catalytic hydrogenation into a corresponding compound of formula I, where Rx constitutes a hydrogen atom, and/or

en forbindelse med formel I, hvor R2utgjør en pyridinring, kan denne ved katalytisk hydrering overføres i en tilsvarende forbindelse med formel I, hvor R2utgjør en piperidinylgruppe, og/eller a compound of formula I, where R2 constitutes a pyridine ring, this can be transferred by catalytic hydrogenation into a corresponding compound of formula I, where R2 constitutes a piperidinyl group, and/or

en forbindelse med formel I, hvor R2utgjør en alkoksyfenyl-eller dialkoksyfenylgruppe, kan denne ved eterspaltning overføres i en tilsvarende forbindelse med formel I, hvor R2utgjør en hydroksyfenyl- eller dihydroksyfenylgruppe, a compound of formula I, where R 2 constitutes an alkoxyphenyl or dihydroxyphenyl group, this can be transferred by ether cleavage into a corresponding compound of formula I, where R 2 constitutes a hydroxyphenyl or dihydroxyphenyl group,

og/ellerand or

en forbindelse med formel I, hvor R2utgjør en alkylmerkaptofenyl- eller dialkylmerkaptofenylgruppe, kan denne oksyderes til en tilsvarende forbindelse med formel I, hvor R2utgjør en alkylsulfinyl-, alkylsulfonyl-, dialkylsulfinyl- eller dialkylsulfonyl-fenylgruppe. a compound of formula I, where R2 is an alkylmercaptophenyl or dialkylmercaptophenyl group, this can be oxidized to a corresponding compound of formula I, where R2 is an alkylsulfinyl, alkylsulfonyl, dialkylsulfinyl or dialkylsulfonylphenyl group.

Den påfølgende alkylering foretas i et egnet oppløsnings-middel som metanol, etanol, dietyleter, aceton, metylenklorid, tetrahydrofuran, dioksan, dimetylformamid eller dimetylsulfoksyd, eventuelt i nærvær av en base som natriumkarbonat, kalium-tert-butylat, trietylamin eller pyridin, hvor de to sistnevnte samtidig kan tjene som oppløsningsmiddel, med et egnet alkyl-eringsmiddel, som metyljodid, dimetylsulfat, etylbromid, dietylsulfat, n-propylbromid, isopropylbromid, etylenoksyd, 2-hydroksy-etylbromid eller formaldehyd/maursyre, eller i nærvær av natriumcyanborhydrid, dersom en tilsvarende karbonylfor-bindelse benyttes, ved temperaturer mellom 0 og 100°C. The subsequent alkylation is carried out in a suitable solvent such as methanol, ethanol, diethyl ether, acetone, methylene chloride, tetrahydrofuran, dioxane, dimethylformamide or dimethylsulfoxide, possibly in the presence of a base such as sodium carbonate, potassium tert-butylate, triethylamine or pyridine, where the the latter two can simultaneously serve as a solvent, with a suitable alkylating agent, such as methyl iodide, dimethyl sulfate, ethyl bromide, diethyl sulfate, n-propyl bromide, isopropyl bromide, ethylene oxide, 2-hydroxy-ethyl bromide or formaldehyde/formic acid, or in the presence of sodium cyanoborohydride, if a corresponding carbonyl compound is used, at temperatures between 0 and 100°C.

Den etterfølgende alkanoylering utføres hensiktsmessig i et oppløsningsmiddel som tetrahydrofuran, dioksan, benzen eller dimetylformamid, eventuelt i nærvær av et kondensasjonsmiddel som tionylklorid, N,N'-dicykloheksylkarbodiimid eller karbonyldiimidazol, fortrinnsvis med det tilsvarende syreanhydrid eller syrehalogenid, ved temperaturer mellom 0 og 100°C, fortrinnsvis ved temperaturer mellom 20 og 50°C. The subsequent alkanoylation is conveniently carried out in a solvent such as tetrahydrofuran, dioxane, benzene or dimethylformamide, optionally in the presence of a condensing agent such as thionyl chloride, N,N'-dicyclohexylcarbodiimide or carbonyldiimidazole, preferably with the corresponding acid anhydride or acid halide, at temperatures between 0 and 100° C, preferably at temperatures between 20 and 50°C.

Den påfølgende katalytiske hydrering utføres fortrinnsvis med hydrogen i nærvær av en hydreringskatalysator, så som platina, palladium/kull eller Raney-nikkel, i et egnet opp-løsningsmiddel, f.eks. i metanol, etanol, tetrahydrofuran, dioksan, iseddik, dimetylformamid eller eddiksyre-etylester, ved temperaturer mellom 20°C og 100°C, fortrinnsvis ved 20-50°C. The subsequent catalytic hydrogenation is preferably carried out with hydrogen in the presence of a hydrogenation catalyst, such as platinum, palladium/charcoal or Raney nickel, in a suitable solvent, e.g. in methanol, ethanol, tetrahydrofuran, dioxane, glacial acetic acid, dimethylformamide or acetic acid ethyl ester, at temperatures between 20°C and 100°C, preferably at 20-50°C.

Den påfølgende eterspaltning utføres i nærvær av en syre som saltsyre, svovelsyre, pyridin-hydroklorid, bortribromid, aluminiumklorid eller tinn(IV)klorid eventuelt i et egnet oppløsningsmiddel, så som metylenklorid, etylenklorid, eller i et overskudd av den anvendte syre, ved temperaturer mellom -10°C og reaksjonsblandingens kokepunkt. Ved eterspaltningen med pyridin-hydroklorid overføres samtidig en forbindelse med formel I, hvori R1utgjør en av de innledningsvis nevnte alkoksyalkylgrupper, i den tilsvarende pyridiniumforbindelse. The subsequent ether cleavage is carried out in the presence of an acid such as hydrochloric acid, sulfuric acid, pyridine hydrochloride, boron tribromide, aluminum chloride or stannous chloride, optionally in a suitable solvent, such as methylene chloride, ethylene chloride, or in an excess of the acid used, at temperatures between -10°C and the boiling point of the reaction mixture. During the ether cleavage with pyridine hydrochloride, a compound of formula I, in which R 1 constitutes one of the initially mentioned alkoxyalkyl groups, is simultaneously transferred into the corresponding pyridinium compound.

Den påfølgende oksydasjon utføres hensiktsmessig i et oppløsningsmiddel eller en oppløsningsrniddelblanding, f . eks . i vann, vann/pyridin, metanol, etanol, aceton, maursyre, iseddik, fortynnet saltsyre eller trifluoreddiksyre, avhengig av det anvendte oksydasjonsmiddel, hensiktsmessig ved temperaturer mellom -80°C og 100°C. The subsequent oxidation is conveniently carried out in a solvent or a solvent mixture, e.g. e.g. in water, water/pyridine, methanol, ethanol, acetone, formic acid, glacial acetic acid, dilute hydrochloric acid or trifluoroacetic acid, depending on the oxidizing agent used, suitably at temperatures between -80°C and 100°C.

For fremstilling av en alkylsulfinylforbindelse med formel I, utføres oksydasjonen hensiktsmessig med en ekvivalent av det anvendte oksydasjonsmiddel, f.eks. med hydrogenperoksyd i iseddik eller maursyre ved 0-20°C eller i aceton ved 0-60°C, For the preparation of an alkylsulfinyl compound of formula I, the oxidation is conveniently carried out with an equivalent of the oxidizing agent used, e.g. with hydrogen peroxide in glacial acetic acid or formic acid at 0-20°C or in acetone at 0-60°C,

med en persyre som permaursyre eller m-klorperbenzosyre i iseddik eller trifluoreddiksyre ved 0-20°C, med natrium-metaperjodat i vandig metanol eller etanol, ved 15-25°C eller med tert-butyl-hypokloritt i metanol ved -80 til -30°G. with a peracid such as permauric acid or m-chloroperbenzoic acid in glacial acetic acid or trifluoroacetic acid at 0-20°C, with sodium metaperiodate in aqueous methanol or ethanol, at 15-25°C or with tert-butyl hypochlorite in methanol at -80 to - 30°G.

For fremstilling" av en alkylsulfonylforbindelse med formel I, utføres oksydasjonen med én eller med flere ekvivalenter av det anvendte oksydasjonsmiddel, f.eks. med hydrogen i iseddik eller i maursyre ved 20-100°C, eller i aceton ved 0-60°C, med en persyre som permaursyre eller m-klorperbenzosyre i iseddik, trifluoreddiksyre eller kloroform ved 0-50°C, eller med bromsyre eller med kaliumpermanganat i iseddik, vann/svovelsyre eller i aceton ved 0-20°C. Dersom en anvendt forbindelse med formel I inneholder en alkylmerkaptogruppe, utføres den påfølgende oksydasjon fortrinnsvis med to eller flere ekvivalenter av det aktuelle oksydasjonsmiddel, og tilsvarende, dersom utgangs-forbindelsen med formel I inneholder en alkylsulfinylgruppe, For the preparation of an alkylsulfonyl compound of formula I, the oxidation is carried out with one or more equivalents of the oxidizing agent used, for example with hydrogen in glacial acetic acid or in formic acid at 20-100°C, or in acetone at 0-60°C , with a peracid such as permauric acid or m-chloroperbenzoic acid in glacial acetic acid, trifluoroacetic acid or chloroform at 0-50°C, or with bromic acid or with potassium permanganate in glacial acetic acid, water/sulfuric acid or in acetone at 0-20°C. If a compound used with formula I contains an alkylmercapto group, the subsequent oxidation is preferably carried out with two or more equivalents of the oxidizing agent in question, and correspondingly, if the starting compound of formula I contains an alkylsulfinyl group,

med minst én ekvivalent.with at least one equivalent.

De oppnådde forbindelsene med formel I kan videre overføres i deres syreaddisjonssalter, spesielt ved farmasøytisk anvendelse, i deres fysiologisk akseptable salter med uorganiske eller organiske syrer. Syrer som kommer i betraktning til formålet er eksempelvis saltsyre, hydrogenbromidsyre, svovelsyre, fosforsyre, fumarsyre, ravsyre, melkesyre, sitronsyre, vinsyre eller maleinsyre. The obtained compounds of formula I can further be transferred in their acid addition salts, especially for pharmaceutical use, in their physiologically acceptable salts with inorganic or organic acids. Acids that come into consideration for the purpose are, for example, hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid, fumaric acid, succinic acid, lactic acid, citric acid, tartaric acid or maleic acid.

Utgangsforbindelsene med de generelle formler II til IV, oppnås ved fremgangsmåter kjent fra litteraturen. The starting compounds with the general formulas II to IV are obtained by methods known from the literature.

Således oppnås eksempelvis 5-isonikotinoylamino-6-nitro-1,3,3-trimetyl-indolin-2-on ved omsetning av 5-acetamino-3,3-dimetyl-indolin-2-on med natriumhydrid eller kalium-tert.-butylat/metyljodid i dimetylformamid. Ved påfølgende nitrering av det således oppnådde 5-acetamino-l,3,3-trimetyl-indolin-2-on med kons. salpetersyre (d = 1,51) og etterfølgende hydrolyse med halvkonsentrert saltsyre, oppnår man 5-amino-6-nitro-l,3,3-trimetyl-indolin-2-on, som ved reduksjon overføres i den tilsvarende 5,6-diaminoforbindelse, eller ved omsetning med isonikotinsyreklorid overføres i 5-isonikotinoylamino-6-nitro-1,3,3-trimetyl-indolin-2-on (se Eksempel A til D). Thus, for example, 5-isonicotinoylamino-6-nitro-1,3,3-trimethyl-indolin-2-one is obtained by reacting 5-acetamino-3,3-dimethyl-indolin-2-one with sodium hydride or potassium tert.- butylate/methyl iodide in dimethylformamide. By subsequent nitration of the thus obtained 5-acetamino-1,3,3-trimethyl-indolin-2-one with conc. nitric acid (d = 1.51) and subsequent hydrolysis with semi-concentrated hydrochloric acid, 5-amino-6-nitro-1,3,3-trimethyl-indolin-2-one is obtained, which upon reduction is transferred into the corresponding 5,6- diamino compound, or by reaction with isonicotinic acid chloride is transferred into 5-isonicotinoylamino-6-nitro-1,3,3-trimethyl-indolin-2-one (see Examples A to D).

De nye forbindelsene med formel I, deres optisk aktive antipoder og deres syreaddisjonssalter, spesielt deres fysiologisk akseptable syreaddisjonssalter med uorganiske eller organiske syrer, har som allerede nevnt, verdifulle farmakologiske egenskaper, spesielt ved at de ved svak påvirkning av blodtrykket, har en positiv inotrop (kardiotonisk) virkning og en antitrombotisk virkning. The new compounds of formula I, their optically active antipodes and their acid addition salts, especially their physiologically acceptable acid addition salts with inorganic or organic acids, have, as already mentioned, valuable pharmacological properties, especially in that they have a positive inotrope ( cardiotonic) effect and an antithrombotic effect.

Eksempelvis ble følgende forbindelserFor example, the following compounds were

A = 5-etyl-7,7-dimetyl-2-(4-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on, A = 5-ethyl-7,7-dimethyl-2-(4-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

B = 5-etyl-7,7-dimetyl-2-(2-furyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on, B = 5-ethyl-7,7-dimethyl-2-(2-furyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

C = 5-etyl-7,7-dimetyl-2-(4-metylsulfonyl-fenyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on, C = 5-ethyl-7,7-dimethyl-2-(4-methylsulfonyl-phenyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one,

D = 5-etyl-7,7-dimetyl-2-(4-metyl-oksazol-5-yl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on D = 5-ethyl-7,7-dimethyl-2-(4-methyl-oxazol-5-yl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one

undersøkt på deres biologiske egenskaper på følgende måte:examined for their biological properties as follows:

1. Bestemmelse av den blodtrykkssenkende og positiv inotrope virkning på anestetiserte katter: Undersøkelsene ble utført på katter som var anestetisert med pentobarbital-natrium (40 mg/kg i.p. + 8 mg/kg/time). Dyrene pustet spontant. Det arterielle blodtrykk ble målt i aorta abdominalis med enStatham-trykkomformer (P 23 Dc). For å fastslå den positive inotrope virkning ble trykket målt med et kateterspiss-manometer (Millar PC-350 A) i det venstre hjerte-kammer. Ut fra dette ble kontraktilitetsparameteren dp/dtmaksoppnådd ved hjelp av en analog differensierer. Testsubstansen ble injisert i en vena femoralis. Som oppløsningsmiddel tjente Polydiol 200. Substansen ble testet på 2 katter, dose 0,3 mg/kg i. v. 1. Determination of the blood pressure-lowering and positive inotropic effect on anesthetized cats: The studies were performed on cats anesthetized with pentobarbital sodium (40 mg/kg i.p. + 8 mg/kg/hour). The animals breathed spontaneously. The arterial blood pressure was measured in the abdominal aorta with a Statham pressure transducer (P 23 Dc). To determine the positive inotropic effect, the pressure was measured with a catheter tip manometer (Millar PC-350 A) in the left heart chamber. Based on this, the contractility parameter dp/dtmax was obtained using an analogue differentiator. The test substance was injected into a femoral vein. Polydiol 200 served as a solvent. The substance was tested on 2 cats, dose 0.3 mg/kg i.v.

Den etterfølgende tabell inneholder middelverdiene:The following table contains the mean values:

I denne sammenheng skal det nevnes at det ikke ble In this context, it should be mentioned that it was not

iakttatt toksiske bivirkninger av testsubstansene ved de biologiske undersøkelsene. observed toxic side effects of the test substances during the biological investigations.

På grunn av deres farmakologiske egenskaper egner forbindelsene med formel I og deres optisk aktive antipoder, samt deres fysiologisk akseptable syreaddisjonssalter med uorganiske eller organiske syrer, seg til behandling av kronisk og akutt hjerteinsuffisiens av forskjellig genese og/eller til profylakse eller behandling av tromboembolier og arterielle tilstoppings-sykdommer. Due to their pharmacological properties, the compounds of formula I and their optically active antipodes, as well as their physiologically acceptable acid addition salts with inorganic or organic acids, are suitable for the treatment of chronic and acute heart failure of various genesis and/or for the prophylaxis or treatment of thromboembolism and arterial constipation diseases.

Til dette formål lar de nye forbindelser seg, eventuelt i kombinasjon med andre virkestoffer, innarbeide i vanlige farmasøytiske anvendelsesformer som tabletter, drasjeer, pulvere, suspensjoner, suppositorier eller ampuller. Enkeltdosen som hos voksne kan gis 1-4x daglig, utgjør herunder 1-50 mg, fortrinnsvis 2-40 mg, ved intravenøs administrasjon, og 5-150 mg, fortrinnsvis 5-100 mg, ved oral administrasjon. For this purpose, the new compounds can be incorporated, possibly in combination with other active substances, into common pharmaceutical application forms such as tablets, dragees, powders, suspensions, suppositories or ampoules. The single dose, which in adults can be given 1-4x daily, comprises 1-50 mg, preferably 2-40 mg, by intravenous administration, and 5-150 mg, preferably 5-100 mg, by oral administration.

Eksempel A Example A

5- acetamido- l- etyl- 3, 3- dimetyl- indolin- 2- on5- acetamido- l- ethyl- 3, 3- dimethyl- indolin- 2- one

218,3 g (1 mol) 5-acetamido-3,3-dimetyl-indolin-2-on ble suspendert ved romtemperatur i 1 liter dimetylformamid og under kraftig omrøring porsjonsvis tilsatt 123,4 g (1,1 mol) kalium-tert-butylat. Temperaturen steg derved til 38°C. Etter videre omrøring i 1/2 time til temperaturen hadde sunket til 18-23°C, ble det under omrøring dråpevis tilsatt 81,6 ml = 119,8 g 218.3 g (1 mol) of 5-acetamido-3,3-dimethyl-indolin-2-one was suspended at room temperature in 1 liter of dimethylformamide and, with vigorous stirring, 123.4 g (1.1 mol) of potassium tert -butylate. The temperature thereby rose to 38°C. After further stirring for 1/2 hour until the temperature had dropped to 18-23°C, 81.6 ml = 119.8 g were added dropwise while stirring

(1,1 mol) etylbromid i løpet av 25 minutter, hvoretter omrøringen ble fortsatt i 1 time ved romtemperatur. Ved en badtemperatur på 50°C ble det deretter under vannstråle-vakuum fordampet 800 ml oppløsningsmiddel, hvorpå residuet ble tilsatt 2,4 liter isvann og omrørt i 1 time. Det utfelte produkt ble suget av, vasket med 1 liter destillert vann og tørket ved 50°C. (1.1 mol) of ethyl bromide over 25 minutes, after which stirring was continued for 1 hour at room temperature. At a bath temperature of 50°C, 800 ml of solvent were then evaporated under a water jet vacuum, after which 2.4 liters of ice water were added to the residue and stirred for 1 hour. The precipitated product was sucked off, washed with 1 liter of distilled water and dried at 50°C.

Utbytte: 197,1 g (80% av det teoretiske),Yield: 197.1 g (80% of the theoretical),

smeltepunkt: 156-157°C.melting point: 156-157°C.

På analog måte ble følgende forbindelser fremstillet: 5-acetamido-l,3,3-trimetyl-indolin-2-on, In an analogous manner, the following compounds were prepared: 5-acetamido-1,3,3-trimethyl-indolin-2-one,

smeltepunkt: 159-161°C. melting point: 159-161°C.

5-acetamido-l-benzyl-3,3-dimetyl-indolin-2-on,5-acetamido-1-benzyl-3,3-dimethyl-indolin-2-one,

smeltepunkt: 169-170°C. melting point: 169-170°C.

5-acetamido-3,3-dimetyl-1-isopropyl-indolin-2-on,5-acetamido-3,3-dimethyl-1-isopropyl-indolin-2-one,

smeltepunkt: 165-166°C.melting point: 165-166°C.

5-acetamido-l-metyl-indolin-2-on,5-acetamido-1-methyl-indolin-2-one,

smeltepunkt: 246-248°C.melting point: 246-248°C.

5-acetamido-l-etyl-3-metyl-indolin-2-on,5-acetamido-1-ethyl-3-methyl-indolin-2-one,

smeltepunkt: 149-150°C. melting point: 149-150°C.

5-acetamido-3,3-dimetyl-l-n-propyl-indolin-2-on,5-acetamido-3,3-dimethyl-1-n-propyl-indolin-2-one,

smeltepunkt: 106-107°C. melting point: 106-107°C.

5-acetamido-3,3-dimetyl-1-(2-metoksy-etyl)-indolin-2-on, 5-acetamido-3,3-dimetyl-l-n-pentyl-indolin-2-on, 5-acetamido-3,3-dimethyl-1-(2-methoxy-ethyl)-indolin-2-one, 5-acetamido-3,3-dimethyl-1-n-pentyl-indolin-2-one,

5-acetamido-l-n-butyl-3,3-dimetyl-indolin-2-on, 5-acetamido-1-n-butyl-3,3-dimethyl-indolin-2-one,

5- (N-metyl-acetamido)-1,3,3-trimetyl-indolin-2-on,5-(N-methyl-acetamido)-1,3,3-trimethyl-indolin-2-one,

smeltepunkt: 137°C melting point: 137°C

6- (N-metyl-acetamido)-l,3,3-trimetyl-indolin-2-on,6-(N-methyl-acetamido)-1,3,3-trimethyl-indolin-2-one,

smeltepunkt: 139-140°C.melting point: 139-140°C.

Eksempel B Example B

l- etyl- 5- amino- 3, 3- dimetyl- 6- nitro- indolin- 2- onl- ethyl- 5- amino- 3, 3- dimethyl- 6- nitro- indolin- 2- one

197 g (0,8 mol) 5-acetamido-l-etyl-3,3-dimetyl-indolin-2-on ble oppløst i 1,3 liter iseddik og i løpet av 20 minutter under omrøring og ved 18-20°C, dråpevis tilsatt 80 ml røkende salpetersyre (d = 1,50). Etter videre omrøring i 10 minutter, ble det foretatt fortynning med isvann til et volum på 10 197 g (0.8 mol) of 5-acetamido-1-ethyl-3,3-dimethyl-indolin-2-one were dissolved in 1.3 liters of glacial acetic acid and during 20 minutes under stirring and at 18-20°C , dropwise added 80 ml fuming nitric acid (d = 1.50). After further stirring for 10 minutes, dilution was made with ice water to a volume of 10

liter. Det utfelte gule 5-acetamido-l-etyl-3,3-dimetyl-6-nitro-indolin-2-on ble suget av, vasket med vann og tilsatt 0,5 liter litres. The precipitated yellow 5-acetamido-1-ethyl-3,3-dimethyl-6-nitro-indolin-2-one was suctioned off, washed with water and added 0.5 liter

6N saltsyre, 0,5 liter metanol og 0,5 liter isopropanol og kokt under tilbakeløpskjøling i 2,5 timer. Etter frafiltrering av noe uløst materiale gjennom et hurtigfilter, ble filtratet tilsatt 1 kg is, hvorpå det orange-farvede produkt ble suget av, vasket med vann og tørket i et omlufts-tørkeskap. 6N hydrochloric acid, 0.5 liters of methanol and 0.5 liters of isopropanol and boiled under reflux for 2.5 hours. After filtering off some undissolved material through a rapid filter, 1 kg of ice was added to the filtrate, after which the orange-coloured product was sucked off, washed with water and dried in a circulating air drying cabinet.

Utbytte: 134 g (68% av det teoretiske),Yield: 134 g (68% of the theoretical),

smeltepunkt: 187-188°C.melting point: 187-188°C.

På analog måte ble følgende forbindelser fremstillet: 5-amino-3,3-dimetyl-1-(2-metoksyetyl)-6-nitro-indolin-2-on, smeltepunkt: 166-167°C. In an analogous manner, the following compounds were prepared: 5-amino-3,3-dimethyl-1-(2-methoxyethyl)-6-nitro-indolin-2-one, melting point: 166-167°C.

5-amino-6-nitro-1,3,3-trimetyl-indolin-2-on,5-amino-6-nitro-1,3,3-trimethyl-indolin-2-one,

smeltepunkt: >290°C. melting point: >290°C.

5-amino-l-benzyl-3,3-dimetyl-6-nitro-indolin-2-on,5-amino-1-benzyl-3,3-dimethyl-6-nitro-indolin-2-one,

smeltepunkt: 117°C. melting point: 117°C.

5-amino-3,3-dimetyl-l-isopropyl-6-nitro-indolin-2-on, smeltepunkt: 205-206°C. 5-amino-3,3-dimethyl-1-isopropyl-6-nitro-indolin-2-one, melting point: 205-206°C.

5-amino-3,3-dimetyl-6-nitro-l-n-pentyl-indolin-2-on, smeltepunkt: 113-114°C. 5-amino-3,3-dimethyl-6-nitro-1-n-pentyl-indolin-2-one, melting point: 113-114°C.

5-amino-l-metyl-6-nitro-indolin-2-on,5-amino-1-methyl-6-nitro-indolin-2-one,

smeltepunkt: 244-246°C. melting point: 244-246°C.

5-amino-l-ety1-3-metyl-6-nitro-indolin-2-on,5-amino-1-ethyl-3-methyl-6-nitro-indolin-2-one,

smeltepunkt: 207-208°C. melting point: 207-208°C.

5-amino-3,3-dimetyl-6-nitro-l-n-propyl-indolin-2-on, smeltepunkt: 186-187°C. 5-amino-3,3-dimethyl-6-nitro-1-n-propyl-indolin-2-one, melting point: 186-187°C.

5-amino-l-n-butyl-3,3-dimetyl-6-nitro-indolin-2-on, smeltepunkt: 92-94°C. 5-amino-1-n-butyl-3,3-dimethyl-6-nitro-indolin-2-one, melting point: 92-94°C.

5- metylamino-6-nitro-1,3,3-trimetyl-indolin-2-on,5- methylamino-6-nitro-1,3,3-trimethyl-indolin-2-one,

smeltepunkt: 236-237°C. melting point: 236-237°C.

6- metylamino-5-nitro-1,3,3-trimetyl-indolin-2-on,6- methylamino-5-nitro-1,3,3-trimethyl-indolin-2-one,

smeltepunkt: 257-258°C.melting point: 257-258°C.

Eksempel C Example C

1- etyl- 5, 6- diamino- 3, 3- dimetyl- indolin- 2- on- dihydroklorid1- ethyl- 5, 6- diamino- 3, 3- dimethyl- indoline- 2- one- dihydrochloride

25 g (0,1 mol) l-etyl-5-amino-3,3-dimetyl-6-nitro-indolin-2- on ble oppløst i 250 ml metanol og 40 ml metanolisk saltsyre, tilsatt 2,5 g 10% palladium/kull og hydrert ved romtemperatur i 2 timer. Katalysatoren ble frafiltrert, filtratet tilsatt 2 liter eter og avkjølt til -20°C.Bunnfallet ble suget av, vasket med eter og tørket i eksikkator. 25 g (0.1 mol) of 1-ethyl-5-amino-3,3-dimethyl-6-nitro-indolin-2-one was dissolved in 250 ml of methanol and 40 ml of methanolic hydrochloric acid, to which was added 2.5 g of 10% palladium/charcoal and hydrated at room temperature for 2 hours. The catalyst was filtered off, 2 liters of ether added to the filtrate and cooled to -20°C. The precipitate was sucked off, washed with ether and dried in a desiccator.

Utbytte: 28,5 g (97,5% av det teoretiske),Yield: 28.5 g (97.5% of the theoretical),

smeltepunkt: >300°C.melting point: >300°C.

Eksempel D Example D

l- etyl- 3, 3- dimetyl- 5- isonikotinoylamido- 6- nitro- indolin- 2- on l- ethyl- 3, 3- dimethyl- 5- isonicotinoylamido- 6- nitro- indolin- 2- one

26,5 g (0,106 mol) l-etyl-5-amino-3,3-dimetyl-6-nitro-indolin-2-on ble oppløst i 300 ml pyridin og ved romtemperatur porsjonsvis tilsatt 26,7 g (0,15 mol) isonikotinsyreklorid-hydroklorid. Etter omrøring i 20 timer ble blandingen langsomt fortynnet med vann. Det gule bunnfall ble suget av, vasket med 500 ml vann, 150 ml isopropanol og 200 ml diisopropyleter og tørket. 26.5 g (0.106 mol) of 1-ethyl-5-amino-3,3-dimethyl-6-nitro-indolin-2-one was dissolved in 300 ml of pyridine and at room temperature 26.7 g (0.15 mol) isonicotinic acid chloride hydrochloride. After stirring for 20 hours, the mixture was slowly diluted with water. The yellow precipitate was suctioned off, washed with 500 ml of water, 150 ml of isopropanol and 200 ml of diisopropyl ether and dried.

Utbytte: 30,2 g (80,5% av det teoretiske),Yield: 30.2 g (80.5% of the theoretical),

smeltepunkt: 192°C.melting point: 192°C.

På analog måte - eller ved oppvarming av de tilsvarende syreklorider med de tilsvarende amino-nitro-indolin-2-oner i klorbenzen til 80-140°C - ble følgende forbindelser fremstillet: 5-isonikotinoylamido-6-nitro-l,3,3-trimetyl-indolin-2-on, smeltepunkt: 250-252°C. l-etyl-3,3-dimetyl-5-(4-metoksy-benzoylamido)-6-nitro-indolin-2-on, smeltepunkt: 158-159°C. 1- etyl-3,3-dimetyl-5-nikotinoylamido-6-nitro-indolin-2-on, smeltepunkt: 161-162°C. 5-(4-metoksy-benzoylamido)-6-nitro-1,3,3-trimetyl-indolin-2- on, smeltepunkt: 217-218°C. 5-nikotinoylamido-6-nitro-l,3,3-trimetyl-indolin-2-on, smeltepunkt: 209°C. 3,3-dimetyl-l-(2-metoksyetyl)-6-nitro-5-pikoloylamido-indolin-2-on, smeltepunkt: 160-161°C. 3,3-dimetyl-l-(2-metoksyetyl)-5-nikotinoylamido-6-nitro-indolin-2-on, smeltepunkt: 132-133°C. 3,3-dimetyl-l-(2-metoksyetyl)-5-(4-metoksy-benzoylamido)-6-nitro-indolin-2-on, smeltepunkt: 158-159°C. 3,3-dimetyl-5-isonikotinoylamido-6-nitro-indolin-2-on, smeltepunkt: 130-131°C. 1- benzyl-3,3-dimetyl-5-isonikotinoylamido-6-nitro-indolin-2- on, smeltepunkt: 162-163°C. l-etyl-5-isonikotinoylamido-3-metyl-6-nitro-indolin-2-on, smeltepunkt: 170-171°C. In an analogous way - or by heating the corresponding acid chlorides with the corresponding amino-nitro-indolin-2-ones in chlorobenzene to 80-140°C - the following compounds were prepared: 5-isonicotinoylamido-6-nitro-1,3,3 -trimethyl-indolin-2-one, melting point: 250-252°C. 1-ethyl-3,3-dimethyl-5-(4-methoxy-benzoylamido)-6-nitro-indolin-2-one, melting point: 158-159°C. 1- ethyl-3,3-dimethyl-5-nicotinoylamido-6-nitro-indolin-2-one, melting point: 161-162°C. 5-(4-Methoxy-benzoylamido)-6-nitro-1,3,3-trimethyl-indolin-2-one, melting point: 217-218°C. 5-nicotinoylamido-6-nitro-1,3,3-trimethyl-indolin-2-one, melting point: 209°C. 3,3-dimethyl-1-(2-methoxyethyl)-6-nitro-5-picoloylamido-indolin-2-one, melting point: 160-161°C. 3,3-dimethyl-1-(2-methoxyethyl)-5-nicotinoylamido-6-nitro-indolin-2-one, melting point: 132-133°C. 3,3-dimethyl-1-(2-methoxyethyl)-5-(4-methoxy-benzoylamido)-6-nitro-indolin-2-one, melting point: 158-159°C. 3,3-dimethyl-5-isonicotinoylamido-6-nitro-indolin-2-one, melting point: 130-131°C. 1-benzyl-3,3-dimethyl-5-isonicotinoylamido-6-nitro-indolin-2-one, melting point: 162-163°C. 1-ethyl-5-isonicotinoylamido-3-methyl-6-nitro-indolin-2-one, melting point: 170-171°C.

l-metyl-5-nikotinoylamido-6-nitro-indolin-2-on,1-methyl-5-nicotinoylamido-6-nitro-indolin-2-one,

smeltepunkt: 209°C. melting point: 209°C.

1- benzyl-3,3-dimetyl-5-(4-metoksy-benzoylamido)-6-nitro-indolin-2-on, 1- benzyl-3,3-dimethyl-5-(4-methoxy-benzoylamido)-6-nitro-indolin-2-one,

smeltepunkt: 147-149°C. melting point: 147-149°C.

6-nitro-5-(3-fenyl-propionamido)-1,3,3-trimetyl-indolin- • 2- on, 6-nitro-5-(3-phenyl-propionamido)-1,3,3-trimethyl-indolin- • 2- one,

smeltepunkt: 138-139°C. melting point: 138-139°C.

6-nitro-5-fenylacetamido-1,3,3-trimetyl-indolin-2-on, smeltepunkt: 138-140°C. 6-nitro-5-phenylacetamido-1,3,3-trimethyl-indolin-2-one, melting point: 138-140°C.

3,3-dimetyl-l-isopropyl-5-nikotinoylamido-6-nitro-indolin-2-on, 3,3-dimethyl-1-isopropyl-5-nicotinoylamido-6-nitro-indolin-2-one,

smeltepunkt: 164-165°C. melting point: 164-165°C.

3,3-dimetyl-l-isopropy1-5-(4-metoksy-benzoylamido)-6-nitro-indolin-2-on, 3,3-dimethyl-1-isopropyl-5-(4-methoxy-benzoylamido)-6-nitro-indolin-2-one,

smeltepunkt: 134-136°C. melting point: 134-136°C.

3,3-dimetyl-5-nikotinoylamido-6-nitro-l-n-pentyl-indolin-2-on, 3,3-dimethyl-5-nicotinoylamido-6-nitro-1-n-pentyl-indolin-2-one,

smeltepunkt: 164-165°C. melting point: 164-165°C.

3,3-dimetyl-5-(4-metoksy-benzoylamido)-6-nitro-l-n-pentyl-indolin-2-on, 3,3-dimethyl-5-(4-methoxy-benzoylamido)-6-nitro-1-n-pentyl-indolin-2-one,

smeltepunkt: 143-145°C. melting point: 143-145°C.

3,3-dimetyl-5-isonikotinoylamido-l-isopropyl-6-nitro-indolin-2-on, 3,3-dimethyl-5-isonicotinoylamido-1-isopropyl-6-nitro-indolin-2-one,

smeltepunkt: 165-166°C. melting point: 165-166°C.

3,3-dimetyl-5-isonikotinoylamido-6-nitro-l-n-pentyl-indolin-2-on, 3,3-dimethyl-5-isonicotinoylamido-6-nitro-1-n-pentyl-indolin-2-one,

smeltepunkt: 143-144°C. melting point: 143-144°C.

l-etyl-5-(3,5-di-tert-butyl-4-hydroksy-benzoylamido)-3,3-dimetyl-6-nitro-indolin-2-on, smeltepunkt: 247-248°C. l-n-butyl-3,3-dimetyl-5-nikotionylamido-6-nitro-indolin-2-on, smeltepunkt: 113-114°C. 3,3-dimetyl-5-(4-metoksy-benzoylamido)-6-nitro-1-n-propyl-indolin-2-on, smeltepunkt: 188-189°C. l-n-butyl-3,3-dimetyl-5-(4-metoksybenzoylamido)-6-nitro-indolin-2-on, smeltepunkt: 175-176°C. 1- n-butyl-3,3-dimetyl-5-isonikotinoylamido-6-nitro-indolin-2- on, smeltepunkt: 133-134°C. l-etyl-3,3-dimetyl-6-nitro-5-(3-tenoylamido)-indolin-2-on, smeltepunkt: 202-203°C. 1- etyl-3,3-dimetyl-5-(3-furoylamido)-6-nitro-indolin-2-on, smeltepunkt: 193-194°C. 3,3-dimetyl-5-(3-furoylamido)-1-isopropyl-6-nitro-indolin-2- on, smeltepunkt: 148-149°C. 3,3-dimetyl-5-(3-furoylamido)-6-nitro-l-n-pentyl-indolin-2-on, smeltepunkt: 103-104°C. 1- etyl-5-(4-amino-3,5-dibrom-benzoylamido)-3,3-dimetyl-6-nitro-indolin-2-on, smeltepunkt: 216-218°C. 3,3-dimetyl-5-nikotionylamido-6-nitro-l-n-propyl-indolin-2-on, smeltepunkt: 147°C. 3,3-dimetyl-5-isonikotinoylamido-6-nitro-l-n-propyl-indolin-2-on, smeltepunkt: 137°C. 3,3-dimetyl-5-(3-furoylamido)-1-(2-metoksyetyl)-6-nitro-indolin-2-on, smeltepunkt: 128-129°C. 3,3-dimetyl-l-isopropyl-6-nitro-5-(3-tenoylamido)-indolin-2- on, smeltepunkt: 153°C. 3,3-dimetyl-l-n-pentyl-6-nitro-5-(3-tenoylamido)-indolin-2-on, smeltepunkt: 115-116°C. 3,3-dimetyl-l-(2-metoksyetyl)-6-nitro-5-(3-tenoylamido)-indolin-2-on, smeltepunkt:133-134°C. l-etyl-3,3-dimetyl-6-nitro-5-(2-pyrazinoylamido)-indolin-2-on, smeltepunkt: 217°C. l-etyl-3,3-dimetyl-5-(2-furoylamido)-6-nitro-indolin-2-on, smeltepunkt: 167°C. l-etyl-3,3-dimety1-6-nitro-5-(2-tenoylamido)-indolin-2-on, smeltepunkt: 177°C. l-etyl-3,3-dimetyl-5-(4-metylmerkapto-benzoylamido)-6-nitro-indolin-2-on, smeltepunkt: 148-150°C. l-etyl-3,3-dimety1-5-(4-dimetylamino-benzoylamido)-6-nitro-indolin-2-on, smeltepunkt: 164-166°C. l-etyl-3,3-dimetyl-5-(2-metoksy-4-metylmerkapto-benzoylamido)-6-nitro-indolin-2-on, smeltepunkt: 219°C. l-etyl-5-(2-kinolin-karbonamido)-3,3-dimetyl-6-nitro-indolin-2-on, smeltepunkt: 220-222°C. l-etyl-5-(4-amino-benzoylamido)-3,3-dimety1-6-nitro-indolin-2-on, smeltepunkt: 180°C. 5-(l-acetyl-4-piperidin-karbonamido)-l-etyl-3,3-dimetyl-6-nitro-indolin-2-on, smeltepunkt: 178°C. 1- etyl-5-(4-klor-benzoylamido)-3,3-dimetyl-6-nitro-indolin-2- on, smeltepunkt: 170-172°C. l-etyl-5-(4-kinolin-karbonamido)-3,3-dimetyl-6-nitro-indolin-2-on, 1-ethyl-5-(3,5-di-tert-butyl-4-hydroxy-benzoylamido)-3,3-dimethyl-6-nitro-indolin-2-one, melting point: 247-248°C. 1-n-butyl-3,3-dimethyl-5-nicothionylamido-6-nitro-indolin-2-one, melting point: 113-114°C. 3,3-dimethyl-5-(4-methoxy-benzoylamido)-6-nitro-1-n-propyl-indolin-2-one, melting point: 188-189°C. 1-n-butyl-3,3-dimethyl-5-(4-methoxybenzoylamido)-6-nitro-indolin-2-one, melting point: 175-176°C. 1-n-butyl-3,3-dimethyl-5-isonicotinoylamido-6-nitro-indolin-2-one, melting point: 133-134°C. 1-ethyl-3,3-dimethyl-6-nitro-5-(3-thenoylamido)-indolin-2-one, melting point: 202-203°C. 1-ethyl-3,3-dimethyl-5-(3-furoylamido)-6-nitro-indolin-2-one, melting point: 193-194°C. 3,3-dimethyl-5-(3-furoylamido)-1-isopropyl-6-nitro-indolin-2-one, melting point: 148-149°C. 3,3-dimethyl-5-(3-furoylamido)-6-nitro-1-n-pentyl-indolin-2-one, melting point: 103-104°C. 1- ethyl-5-(4-amino-3,5-dibromo-benzoylamido)-3,3-dimethyl-6-nitro-indolin-2-one, melting point: 216-218°C. 3,3-dimethyl-5-nicothionylamido-6-nitro-1-n-propyl-indolin-2-one, melting point: 147°C. 3,3-dimethyl-5-isonicotinoylamido-6-nitro-1-n-propyl-indolin-2-one, melting point: 137°C. 3,3-dimethyl-5-(3-furoylamido)-1-(2-methoxyethyl)-6-nitro-indolin-2-one, melting point: 128-129°C. 3,3-dimethyl-1-isopropyl-6-nitro-5-(3-thenoylamido)-indolin-2-one, melting point: 153°C. 3,3-dimethyl-1-n-pentyl-6-nitro-5-(3-thenoylamido)-indolin-2-one, melting point: 115-116°C. 3,3-dimethyl-1-(2-methoxyethyl)-6-nitro-5-(3-thenoylamido)-indolin-2-one, melting point: 133-134°C. 1-ethyl-3,3-dimethyl-6-nitro-5-(2-pyrazinoylamido)-indolin-2-one, melting point: 217°C. 1-ethyl-3,3-dimethyl-5-(2-furoylamido)-6-nitro-indolin-2-one, melting point: 167°C. 1-ethyl-3,3-dimethyl-6-nitro-5-(2-thenoylamido)-indolin-2-one, melting point: 177°C. 1-ethyl-3,3-dimethyl-5-(4-methylmercapto-benzoylamido)-6-nitro-indolin-2-one, melting point: 148-150°C. 1-ethyl-3,3-dimethyl-5-(4-dimethylamino-benzoylamido)-6-nitro-indolin-2-one, melting point: 164-166°C. 1-ethyl-3,3-dimethyl-5-(2-methoxy-4-methylmercapto-benzoylamido)-6-nitro-indolin-2-one, melting point: 219°C. 1-ethyl-5-(2-quinoline-carbonamido)-3,3-dimethyl-6-nitro-indolin-2-one, melting point: 220-222°C. 1-ethyl-5-(4-amino-benzoylamido)-3,3-dimethyl-6-nitro-indolin-2-one, melting point: 180°C. 5-(1-acetyl-4-piperidine-carbonamido)-1-ethyl-3,3-dimethyl-6-nitro-indolin-2-one, melting point: 178°C. 1- ethyl-5-(4-chloro-benzoylamido)-3,3-dimethyl-6-nitro-indolin-2-one, melting point: 170-172°C. 1-ethyl-5-(4-quinoline-carbonamido)-3,3-dimethyl-6-nitro-indolin-2-one,

smeltepunkt: 239°C. melting point: 239°C.

l-etyl-5-(4-kinolin-karbonamido)-3,3-dimetyl-6-nitro- 1-ethyl-5-(4-quinoline-carbonamido)-3,3-dimethyl-6-nitro-

indolin-2-on,indolin-2-one,

smeltepunkt: 239°C. melting point: 239°C.

l-etyl-5-(4-kinolin-karbonamido)-3,3-dimetyl-6-nitro-indolin-2-on, smeltepunkt: 239°C. l-etyl-3,3-dimetyl-5-(2-dimetylamino-nikotinoylamido)-6-nitro-indolin-2-on, smeltepunkt: 140-142°C. l-etyl-3,3-dimetyl-5-(2-morfolino-nikotinoylamido)-6-nitro-indolin-2-on, smeltepunkt: 167°C. l-etyl-5-(2,6-diklor-isonikotinoylamido)-3,3-dimetyl-6-nitro-indolin-2-on, smeltepunkt: 197°C. l-etyl-5-(2-klor-6-morfolino-isonikotinoylamido)-3,3-dimetyl-6-nitro-indolin-2-on, smeltepunkt: 208°C. l-etyl-3,3-dimety1-5-(pyrimidin-5-karbonamido)-6-nitro-indolin-2-on, 1-ethyl-5-(4-quinoline-carbonamido)-3,3-dimethyl-6-nitro-indolin-2-one, melting point: 239°C. 1-ethyl-3,3-dimethyl-5-(2-dimethylamino-nicotinoylamido)-6-nitro-indolin-2-one, melting point: 140-142°C. 1-ethyl-3,3-dimethyl-5-(2-morpholino-nicotinoylamido)-6-nitro-indolin-2-one, melting point: 167°C. 1-ethyl-5-(2,6-dichloro-isonicotinoylamido)-3,3-dimethyl-6-nitro-indolin-2-one, melting point: 197°C. 1-ethyl-5-(2-chloro-6-morpholino-isonicotinoylamido)-3,3-dimethyl-6-nitro-indolin-2-one, melting point: 208°C. 1-ethyl-3,3-dimethyl-5-(pyrimidine-5-carbonamido)-6-nitro-indolin-2-one,

smeltepunkt: 215°C. melting point: 215°C.

3,3-dimetyl-l-n-propyl-6-nitro-5-(2-tenoylamido)-indolin-2-on, smeltepunkt: 140°C. 3,3-dimethyl-1-n-propyl-6-nitro-5-(2-thenoylamido)-indolin-2-one, melting point: 140°C.

3,3-dimetyl-5-(2-furoylamido)-6-nitro-1-n-propyl-indolin-2-on, smeltepunkt: 187°C. 3,3-dimethyl-5-(2-furoylamido)-6-nitro-1-n-propyl-indolin-2-one, melting point: 187°C.

3,3-dimety1-5-(4-metylmerkapto-benzoylamido)-6-nitro-1-n-propyl- indolin-2-on, 3,3-dimethyl-5-(4-methylmercapto-benzoylamido)-6-nitro-1-n-propyl-indolin-2-one,

smeltepunkt: 156-158°C. melting point: 156-158°C.

3,3-dimetyl-6-nitro-l-n-pentyl-5-(2-tenoylamido)-indolin-2-on, smeltepunkt: 125-127°C. 3,3-dimethyl-6-nitro-1-n-pentyl-5-(2-thenoylamido)-indolin-2-one, melting point: 125-127°C.

1- etyl-5-(4-cyan-benzoylamido)-3,3-dimetyl-6-nitro-indolin-2- on, 1- ethyl-5-(4-cyano-benzoylamido)-3,3-dimethyl-6-nitro-indolin-2-one,

smeltepunkt: 197-199°C. melting point: 197-199°C.

1- etyl-5-(2-klor-benzoylamido)-3,3-dimetyl-6-nitro-indolin-2- on, 1- ethyl-5-(2-chloro-benzoylamido)-3,3-dimethyl-6-nitro-indolin-2-one,

smeltepunkt: 169°C. melting point: 169°C.

5- (2-fenyl-akrylamido)-6-nitro-1,3,3-trimetyl-indolin-2-on, smeltepunkt: 209-211°C. 5-(2-phenyl-acrylamido)-6-nitro-1,3,3-trimethyl-indolin-2-one, melting point: 209-211°C.

6- nitro-5-(2-pyrazinoylamido)-1,3,3-trimetyl-indolin-2-on, 6-nitro-5-(2-pyrazinoylamido)-1,3,3-trimethyl-indolin-2-one,

smeltepunkt: > 280°C. melting point: > 280°C.

6-nitro-5-(2-tenoylamido)-1,3,3-trimetyl-indolin-2-on, smeltepunkt: 220°C. 6-nitro-5-(2-thenoylamido)-1,3,3-trimethyl-indolin-2-one, melting point: 220°C.

3,3-dimety1-6-nitro-1-n-propyl-5-(2-pyrazinoylamido)-indolin-2-on, 3,3-dimethyl-6-nitro-1-n-propyl-5-(2-pyrazinoylamido)-indolin-2-one,

smeltepunkt: 185°C. melting point: 185°C.

l-etyl-3,3-dimety1-5-(4-metyl-5-oksazolyl-karbonamido)-6-nitro-indolin-2-on, smeltepunkt: 230°C. l-etyl-5-(4-amino-3,5-diklor-benzoylamido)-3,3-dimety1-6-nitro-indolin-2-on, smeltepunkt: 226-228°C. 1- etyl-3,3-dimetyl-6-nitro-5-(pyrimidin-4-karbonamido)-indolin-2-on, smeltepunkt: 208°C. 3,3-dimetyl-6-nitro-l-n-pentyl-5-(2-pyrazinoylamido)-indolin-2- on, smeltepunkt: 138°C. 3 , 3-dime-tyl-5 - ( 2-f uroylamido) - 6-nit ro-l-n-pentyl-indolin-2-on, smeltepunkt: 135°C. 6-nitro-5-(N-metyl-isonikotinoylamido)-1,3,3-trimetyl-indolin-2-on, smeltepunkt: 190-192°C. 5-nitro-6-(N-metyl-isonikotinoylamido)-1,3,3-trimetyl-indolin-2-on, smeltepunkt: 188-189°C. 5-isonikotinoylamido-l-metyl-6-nitro-indolin-2-on, smeltepunkt: 239-240°C. 3,3-dimety1-5-(4-metylmerkapto-benzoylamido)-6-nitro-1-n-pentyl-indolin-2-on, smeltepunkt: 134°C. 3,3-dimetyl-l-(2-metoksyetyl)-5-(5-mety1-3-furoylamido)-6-nitro-indolin-2-on, smeltepunkt: 144°C. l-etyl-3,3-dimety1-5-(5-mety1-3-furoylamido)-6-nitro-indolin-2-on, 1-ethyl-3,3-dimethyl-5-(4-methyl-5-oxazolyl-carbonamido)-6-nitro-indolin-2-one, melting point: 230°C. 1-ethyl-5-(4-amino-3,5-dichloro-benzoylamido)-3,3-dimethyl-6-nitro-indolin-2-one, melting point: 226-228°C. 1- ethyl-3,3-dimethyl-6-nitro-5-(pyrimidine-4-carbonamido)-indolin-2-one, melting point: 208°C. 3,3-dimethyl-6-nitro-1-n-pentyl-5-(2-pyrazinoylamido)-indolin-2-one, melting point: 138°C. 3,3-dimethyl-5-(2-fluoroylamido)-6-nitro-1-n-pentyl-indolin-2-one, melting point: 135°C. 6-nitro-5-(N-methyl-isonicotinoylamido)-1,3,3-trimethyl-indolin-2-one, melting point: 190-192°C. 5-nitro-6-(N-methyl-isonicotinoylamido)-1,3,3-trimethyl-indolin-2-one, melting point: 188-189°C. 5-isonicotinoylamido-1-methyl-6-nitro-indolin-2-one, melting point: 239-240°C. 3,3-dimethyl-5-(4-methylmercapto-benzoylamido)-6-nitro-1-n-pentyl-indolin-2-one, melting point: 134°C. 3,3-dimethyl-1-(2-methoxyethyl)-5-(5-methyl-3-furoylamido)-6-nitro-indolin-2-one, melting point: 144°C. 1-ethyl-3,3-dimethyl-5-(5-methyl-3-furoylamido)-6-nitro-indolin-2-one,

smeltepunkt: 152-154°C. melting point: 152-154°C.

3,3-dimetyl-1-isopropyl-5-(5-metyl-3-furoylamido)-6-nitro- 3,3-dimethyl-1-isopropyl-5-(5-methyl-3-furoylamido)-6-nitro-

indolin-2-on,indolin-2-one,

smeltepunkt: 155°C. melting point: 155°C.

3,3-dimetyl-5-(5-metyl-3-furoylamido)-6-nitro-l-n-pentyl-indolin-2-on, 3,3-dimethyl-5-(5-methyl-3-furoylamido)-6-nitro-1-n-pentyl-indolin-2-one,

smeltepunkt: 93-95°C. melting point: 93-95°C.

l-etyl-5-benzoylamido-3,3-dimetyl-6-nitro-indolin-2-on, smeltepunkt: 172-173°C. l-etyl-5-butyrylamido-3,3-dimetyl-6-nitro-indolin-2-on, smeltepunkt: 99-100°C. l-etyl-3,3-dimetyl-6-nitro-5-(2-tienyl-acetamido)-indolin-2-on, smeltepunkt: 158°C. l-etyl-3,3-dimetyl-6-nitro-5-(3-tienyl-acetamido)-indolin-2-on, smeltepunkt: 160°C. l-n-butyl-3,3-dimetyl-6-nitro-5-(2-tenoylamido)-indolin-2-on, smeltepunkt: 143°C. l-n-butyl-3,3-dimetyl-6-nitro-5-(3-tienyl-acetamido)-indolin-2-on, 1-ethyl-5-benzoylamido-3,3-dimethyl-6-nitro-indolin-2-one, melting point: 172-173°C. 1-ethyl-5-butyrylamido-3,3-dimethyl-6-nitro-indolin-2-one, melting point: 99-100°C. 1-ethyl-3,3-dimethyl-6-nitro-5-(2-thienyl-acetamido)-indolin-2-one, melting point: 158°C. 1-ethyl-3,3-dimethyl-6-nitro-5-(3-thienyl-acetamido)-indolin-2-one, melting point: 160°C. 1-n-butyl-3,3-dimethyl-6-nitro-5-(2-thenoylamido)-indolin-2-one, melting point: 143°C. 1-n-butyl-3,3-dimethyl-6-nitro-5-(3-thienyl-acetamido)-indolin-2-one,

olje, Rf-verdi: 0,61 (Kiselgel, etylenklorid/aceton = 20:1) 1- n-butyl-3,3-dimetyl-6-nitro-5-(2-tienyl-acetamido)-indolin-2-on, oil, Rf value: 0.61 (Silica gel, ethylene chloride/acetone = 20:1) 1-n-butyl-3,3-dimethyl-6-nitro-5-(2-thienyl-acetamido)-indolin-2- on

olje, Rf-verdi: 0,62 (Kiselgel, etylenklorid/aceton = 20:1). oil, Rf value: 0.62 (Silica gel, ethylene chloride/acetone = 20:1).

Eksempel 1 Example 1

2- (4-pyridyl)-5,7,7-trimetyl-6,7-dihydro-3H,5H-pyrrolo-[ 2, 3- f] benzimidazol- 6- on 2-(4-pyridyl)-5,7,7-trimethyl-6,7-dihydro-3H,5H-pyrrolo-[2,3-f]benzimidazol-6-one

1,95 g (5,7 mmol) 5-isonikotinoylamido-6-nitro-l,3,3-trimetyl-indolin-2-on ble oppløst i 60 ml eddiksyre, omsatt med 1 g Raney-nikkel og i løpet av 4 timer hydrert i autoklav ved 80°C under 5 bar hydrogentrykk. Deretter ble katalysatoren frafiltrert, filtratet inndampet, utrørt med etanol/vann, gjort alkalisk med vandig ammoniakk og suget av. 1.95 g (5.7 mmol) of 5-isonicotinoylamido-6-nitro-1,3,3-trimethyl-indolin-2-one was dissolved in 60 ml of acetic acid, reacted with 1 g of Raney nickel and during 4 hours hydrated in an autoclave at 80°C under 5 bar hydrogen pressure. The catalyst was then filtered off, the filtrate evaporated, stirred with ethanol/water, made alkaline with aqueous ammonia and sucked off.

Utbytte: 1 g (58,5% av det teoretiske),Yield: 1 g (58.5% of the theoretical),

smeltepunkt: fra 161°C (dekomp.; 30% etanol)melting point: from 161°C (decomp.; 30% ethanol)

C17H16N40 x 0,4 H20 (299,55) C17H16N40 x 0.4 H2O (299.55)

Beregnet: C, 68,17; H, 5,65; N, 18,70Calculated: C, 68.17; H, 5.65; N, 18.70

Funnet: C, 68,13; H, 5,77 N, 19,00 Found: C, 68.13; H, 5.77 N, 19.00

Eksempel 2 Example 2

5-etyl-7,7-dimetyl-2-(4-pyridyl)-6,7-dihydro-3H,5H-pyrrolo-[ 2, 3- f ] benzimidazol- 6- on 5-ethyl-7,7-dimethyl-2-(4-pyridyl)-6,7-dihydro-3H,5H-pyrrolo-[2,3-f]benzimidazol-6-one

Fremstillet analogt med Eksempel 1 fra l-etyl-3,3-dimetyl-5-isonikotinoylamido-6-nitro-indolin-2-on og hydrogen/Raney-nikkel. Prepared analogously to Example 1 from 1-ethyl-3,3-dimethyl-5-isonicotinoylamido-6-nitro-indolin-2-one and hydrogen/Raney nickel.

Utbytte: 55% av det teoretiske,Yield: 55% of the theoretical,

smeltepunkt: 297-298°C (isopropanol/diisopropyleter)melting point: 297-298°C (isopropanol/diisopropyl ether)

C18<H>18N40 (306, 37 ) C18<H>18N40 (306, 37 )

Beregnet; C, 70,57; H, 5,92; N, 18,29Calculated; C, 70.57; H, 5.92; N, 18,29

Funnet: C, 70,60; H, 6,18; N, 18,10 Found: C, 70.60; H, 6.18; N, 18,10

Eksempel 3 Example 3

5-etyl-7,7-dimetyl-2-(4-metoksyfenyl)-6,7-dihydro-3H,5H-pyrrolo[ 2, 3- f] benzimidazol- 6- on 5-ethyl-7,7-dimethyl-2-(4-methoxyphenyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one

Fremstillet analogt med Eksempel 1 fra l-etyl-3,3-dimetyl-5-(4-metoksy-benzoylamino)-6-nitro-indolin-2-on og hydrogen/Raney-nikkel. Prepared analogously to Example 1 from 1-ethyl-3,3-dimethyl-5-(4-methoxy-benzoylamino)-6-nitro-indolin-2-one and hydrogen/Raney nickel.

Utbytte: 78% av det teoretiske,Yield: 78% of the theoretical,

smeltepunkt: 275-277°C (isopropanol/dietyleter)melting point: 275-277°C (isopropanol/diethyl ether)

C20<H>12N3<0>2( 335 ,41) C20<H>12N3<0>2( 335 .41)

Beregnet: C, 71,62; H, 6,31; N, 12,53Calculated: C, 71.62; H, 6.31; N, 12.53

Funnet: C, 71,83; H, 6,48; N, 12,65 Found: C, 71.83; H, 6.48; N, 12.65

Eksempel 4 Example 4

5-etyl-7,7-dimetyl-2-(3-pyridyl)-6,7-dihydro-3H,5H-pyrrolo-[ 2 , 3- f ] benzimidazol- 6- on 5-ethyl-7,7-dimethyl-2-(3-pyridyl)-6,7-dihydro-3H,5H-pyrrolo-[2,3-f]benzimidazol-6-one

Fremstillet analogt med Eksempel 1 fra l-etyl-3,3-dimetyl-5-nikotinoylamido-6-nitro-indolin-2-on og hydrogen/Raney-nikkel. Utbytte: 45% av det teoretiske, Prepared analogously to Example 1 from 1-ethyl-3,3-dimethyl-5-nicotinoylamido-6-nitro-indolin-2-one and hydrogen/Raney nickel. Yield: 45% of the theoretical,

smeltepunkt: 299-300°C (isopropanol/diisopropyleter)melting point: 299-300°C (isopropanol/diisopropyl ether)

C18<H>18N40 (306,37) C18<H>18N40 (306.37)

Beregnet: C, 70,57; H, 5,92; N, 18,29Calculated: C, 70.57; H, 5.92; N, 18,29

Funnet: C, 70,70; H, 6,14; N, 18,42 Found: C, 70.70; H, 6.14; N, 18.42

Eksempel 5 Example 5

2-(4-metoksyfenyl)-5,7,7-trimetyl-6,7-dihydro-3H,5H-pyrrolo-[ 2 , - 3f ] benzimidazol- 6- on 2-(4-Methoxyphenyl)-5,7,7-trimethyl-6,7-dihydro-3H,5H-pyrrolo-[2,-3f]benzimidazol-6-one

Fremstillet analogt med Eksempel 1 fra 5-(4-metoksy-benzoylamino)-6-nitro-l,3,3-trimetyl-indolin-2-on og hydrogen/- Raney-nikkel. Prepared analogously to Example 1 from 5-(4-methoxy-benzoylamino)-6-nitro-1,3,3-trimethyl-indolin-2-one and hydrogen/Raney nickel.

Utbytte: 60% av det teoretiske,Yield: 60% of the theoretical,

smeltepunkt: 217-218°C (etylacetat/diisopropyleter).melting point: 217-218°C (ethyl acetate/diisopropyl ether).

C19<H>19N302(321,38) C19<H>19N302(321.38)

Beregnet: C, 71,00; H, 5,96; N, 13,08Calculated: C, 71.00; H, 5.96; N, 13.08

Funnet: C, 70,75; H, 5,94; N, 12,98 Found: C, 70.75; H, 5.94; N, 12.98

Eksempel 6 Example 6

2-(3-pyridyl)-5,7,7-trimetyl-6,7-dihydro-3H,5H-pyrrolo-[ 2, 3- f] benzimidazol- 6- on x 0, 5 H20 2-(3-pyridyl)-5,7,7-trimethyl-6,7-dihydro-3H,5H-pyrrolo-[2,3-f]benzimidazol-6-one x 0.5 H2O

Fremstillet analogt med Eksempel 1 fra 5-nikotinoylamido-6-nitro-l,3,3-trimetyl-indolin-2-on og hydrogen/Raney-nikkel. Utbytte: 66% av det teoretiske, Prepared analogously to Example 1 from 5-nicotinoylamido-6-nitro-1,3,3-trimethyl-indolin-2-one and hydrogen/Raney nickel. Yield: 66% of the theoretical,

smeltepunkt: 297-298°C (etylacetat/diisopropyleter)melting point: 297-298°C (ethyl acetate/diisopropyl ether)

C17H16N40 x 0,5 H20 ( 301,35 ) C17H16N40 x 0.5 H20 ( 301.35 )

Beregnet: C, 67,75; H, 5,68; N, 18,59Calculated: C, 67.75; H, 5.68; N, 18.59

Funnet: C, 67,58; H, 5,73; N, 18,40 Found: C, 67.58; H, 5.73; N, 18.40

Eksempel 7 Example 7

7,7-dimetyl-5-(2-metoksyetyl)-2-(2-pyridyl)-6,7-dihydro-3H, 5H- pyrrolo[ 2, 3- f] benzimidazol- 6- on 7,7-dimethyl-5-(2-methoxyethyl)-2-(2-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one

Fremstillet analogt med Eksempel 1 fra 3,3-dimetyl-l-(2-metoksyetyl)-6-nitro-5-pikoloylamino-indolin-2-on og hydrogen/- Raney-nikkel. Prepared analogously to Example 1 from 3,3-dimethyl-1-(2-methoxyethyl)-6-nitro-5-picoloylamino-indolin-2-one and hydrogen/Raney nickel.

Utbytte: 28% av det teoretiske,Yield: 28% of the theoretical,

smeltepunkt: 216-217°C (etylacetat/diisopropyleter)melting point: 216-217°C (ethyl acetate/diisopropyl ether)

C19<H>20N4<0>2(336,40) C19<H>20N4<0>2(336.40)

Beregnet: C, 67,84; H, 5,99; N, 16,66Calculated: C, 67.84; H, 5.99; N, 16.66

Funnet: C, 68,10; H, 6,05; N, 16,49 Found: C, 68.10; H, 6.05; N, 16.49

Eksempel 8 Example 8

7,7-dimetyl-5-(2-metoksyetyl)-2-(3-pyridyl) -6,7-dihydro-3H, 5H- pyrrolo[ 2 , 3- f ] benzimidazol- 6- on 7,7-dimethyl-5-(2-methoxyethyl)-2-(3-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one

Fremstillet analogt med Eksempel 1 fra 3,3-dimetyl-l-(2-metoksyetyl)-5-nikotionylamido-6-nitro-indolin-2-on og hydrogen/Raney-nikkel. Prepared analogously to Example 1 from 3,3-dimethyl-1-(2-methoxyethyl)-5-nicothionylamido-6-nitro-indolin-2-one and hydrogen/Raney nickel.

Utbytte: 39% av det teoretiske,Yield: 39% of the theoretical,

smeltepunkt: 202-203°C (etylacetat/diisopropyleter)melting point: 202-203°C (ethyl acetate/diisopropyl ether)

Cig<H>20<N>402(336,40) Cig<H>20<N>402(336.40)

Beregnet: C, 67,84; H, 5,99; N, 16,66Calculated: C, 67.84; H, 5.99; N, 16.66

Funnet: C, 68,21; H, 6,13; N, 16,55 Found: C, 68.21; H, 6.13; N, 16.55

Eksempel 9 Example 9

7,7-dimetyl-5-(2-metoksyetyl)-2-(4-metoksyfenyl) -6,7-dihydro-3H, 5H- pyrrolo[ 2 , 3- f ] benzimidazol- 6- on 7,7-dimethyl-5-(2-methoxyethyl)-2-(4-methoxyphenyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one

Fremstillet analogt med Eksempel 1 fra 3,3-dimetyl-l-(2-metoksyetyl)-5-(4-metoksy-benzoylamino)-6-nitro-indolin-2-on og hydrogen/Raney-nikkel. Prepared analogously to Example 1 from 3,3-dimethyl-1-(2-methoxyethyl)-5-(4-methoxy-benzoylamino)-6-nitro-indolin-2-one and hydrogen/Raney nickel.

Utbytte: 78,8% av det teoretiske,Yield: 78.8% of the theoretical,

smeltepunkt: 232-233°C (etylacetat/diisopropyleter)melting point: 232-233°C (ethyl acetate/diisopropyl ether)

C21<H>23N303(365 ,44) C21<H>23N303(365 .44)

Beregnet: C, 69,02; H, 6,34; N, 11,50Calculated: C, 69.02; H, 6.34; N, 11.50

Funnet: C, 69,33; H, 6,36; N, 11,75 Found: C, 69.33; H, 6.36; N, 11.75

Eksempel 10 Example 10

2-(4-hydroksyfenyl)-5,7,7-trimetyl-6,7-dihydro-3H,5H-pyrrolo-[ 2, 3- f] benzimidazol- 6- on x 0, 5 H20 2-(4-Hydroxyphenyl)-5,7,7-trimethyl-6,7-dihydro-3H,5H-pyrrolo-[2,3-f]benzimidazol-6-one x 0.5 H20

1,5 g (4,6 mmol) 2-(4-metoksyfenyl)-5,7,7-trimetyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on ble oppløst i 100 ml vannfri etylenklorid og ved -20°C tilsatt 1,17 g (4,6 mmol) bortribromid. Etter omrøring ved romtemperatur i 3 dager ble ytterligere 1,17 g bortribromid tilsatt og omrøringen fortsatt i 2 dager ved romtemperatur. Deretter ble reaksjonsblandingen tilsatt etanol/vann = 1:1 og residuet etter avdestillering av oppløsningsmidlet, oppløst i fortynnet natronlut og ekstrahert med kloroform/etanol = 4:1. Den vandig-alkaliske fase ble tilsatt aktivkull, og etter en stund ble aktivkullet frafiltrert. Filtratet ble justert til pH 6 ved tilsetning av 1.5 g (4.6 mmol) of 2-(4-methoxyphenyl)-5,7,7-trimethyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one was dissolved in 100 ml anhydrous ethylene chloride and at -20°C added 1.17 g (4.6 mmol) boron tribromide. After stirring at room temperature for 3 days, a further 1.17 g of boron tribromide was added and stirring continued for 2 days at room temperature. Ethanol/water = 1:1 was then added to the reaction mixture and the residue after distilling off the solvent, dissolved in dilute caustic soda and extracted with chloroform/ethanol = 4:1. Activated carbon was added to the aqueous-alkaline phase, and after a while the activated carbon was filtered off. The filtrate was adjusted to pH 6 by adding

fortynnet eddiksyre, bunnfallet suget av, vasket med vann og tørket ved 60°C. dilute acetic acid, the precipitate suctioned off, washed with water and dried at 60°C.

Utbytte: 1,03 g (69% av det teoretiske),Yield: 1.03 g (69% of theoretical),

smeltepunkt: 211°Cmelting point: 211°C

C18H17N302x 0, 5 H20 (316,37) C18H17N302x 0.5H2O (316.37)

Beregnet: C, 68,34; H, 5,74; N, 13,28Calculated: C, 68.34; H, 5.74; N, 13,28

Funnet: C, 68,61; H, 5,55; N, 13,27 Found: C, 68.61; H, 5.55; N, 13.27

Eksempel 11 Example 11

5-etyl-7,7-dimetyl-2-(4-hydroksyfenyl)-6,7-dihydro-3H,5H-pyrrolo[ 2, 3- f] benzimidazol- 6- on x 2 H20 5-ethyl-7,7-dimethyl-2-(4-hydroxyphenyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one x 2 H20

En blanding av 1,7 g (5 mmol) 5-etyl-7,7-dimetyl-2-(4-metoksyfenyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on og 17 g pyridin-hydroklorid ble omrørt i 4 timer ved 180°C. Etter avkjølingen ble blandingen tilsatt vann og det uløste materialet frafiltrert. Det oppnådde residuum ble oppløst i 0,1N natronlut og ekstrahert med kloroform/metanol (4:1). Den vandig-alkaliske fase ble tilsatt aktivkull som etter en stund ble frafiltrert. Ved tilsetning av fortynnet eddiksyre ble filtratet bragt til pH 5-6, hvorpå det utfelte bunnfall ble suget av, vasket med vann og tørket. A mixture of 1.7 g (5 mmol) of 5-ethyl-7,7-dimethyl-2-(4-methoxyphenyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazole-6 -one and 17 g of pyridine hydrochloride were stirred for 4 hours at 180°C. After cooling, water was added to the mixture and the undissolved material was filtered off. The obtained residue was dissolved in 0.1N caustic soda and extracted with chloroform/methanol (4:1). Activated charcoal was added to the aqueous-alkaline phase, which was filtered off after a while. By adding diluted acetic acid, the filtrate was brought to pH 5-6, after which the precipitate that had formed was sucked off, washed with water and dried.

Utbytte: 1,5 g (82,8% av det teoretiske),Yield: 1.5 g (82.8% of the theoretical),

smeltepunkt: fra 295°Cmelting point: from 295°C

C19H19N302x 2 H20 (357 ,42) C19H19N302x 2 H2O (357 .42)

Beregnet: C, 63,85; H, 6,49; N, 11,76Calcd: C, 63.85; H, 6.49; N, 11.76

Funnet: C, 63,85; H, 6,27; N, 12,01 Found: C, 63.85; H, 6.27; N, 12.01

Eksempel 12 Example 12

7,7-dimetyl-5-(2-metoksyetyl)-2-(4-pyridyl)-6,7-dihydro-3H, 5H- pyrrolo[ 2, 3- f] benzimidazol- 6- on 7,7-dimethyl-5-(2-methoxyethyl)-2-(4-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one

Fremstillet analogt med Eksempel 1 fra 3,3-dimetyl-5-isonikotinoylamido-6-nitro-indolin-2-on. Prepared analogously to Example 1 from 3,3-dimethyl-5-isonicotinoylamido-6-nitro-indolin-2-one.

Utbytte: 72% av det teoretiske,Yield: 72% of the theoretical,

smeltepunkt: 255-256°C (etylacetat)melting point: 255-256°C (ethyl acetate)

C19<H>20N402(336,40) C19<H>20N402(336.40)

Beregnet: C, 67,84; H, 5,99; N, 16,66Calculated: C, 67.84; H, 5.99; N, 16.66

Funnet: C, 67,90; H, 5,78; N, 16,48 Found: C, 67.90; H, 5.78; N, 16.48

Eksempel 13 Example 13

5-benzyl-7,7-dimetyl-2-(4-pyridyl)-6,7-dihydro-3H,5H-pyrrolo-[ 2, 3- f] benzimidazol- 6- on x 0, 25 H20 5-benzyl-7,7-dimethyl-2-(4-pyridyl)-6,7-dihydro-3H,5H-pyrrolo-[2,3-f]benzimidazol-6-one x 0.25 H20

Fremstillet analogt med Eksempel 1 fra l-benzyl-3,3-dimetyl-5-isonikotionylamido-6-nitro-indolin-2-on. Prepared analogously to Example 1 from 1-benzyl-3,3-dimethyl-5-isonicothionylamido-6-nitro-indolin-2-one.

Utbytte: 78% av det teoretiske,Yield: 78% of the theoretical,

smeltepunkt: fra 131°C (etylacetat)melting point: from 131°C (ethyl acetate)

C23H20N40 x 0,25 H20 (368,44) C23H20N40 x 0.25 H2O (368.44)

Beregnet: C, 74,04; H, 5,54; N, 15,02Calculated: C, 74.04; H, 5.54; N, 15.02

Funnet: C, 74,10; H, 5,68; N, 15,02 Found: C, 74.10; H, 5.68; N, 15.02

Eksempel 14 Example 14

5-etyl-7-metyl-2-(4-pyridyl)-6,7-dihydro-3H,5H-pyrrolo-[ 2, 3- f] benzimidazol- 6- on 5-ethyl-7-methyl-2-(4-pyridyl)-6,7-dihydro-3H,5H-pyrrolo-[2,3-f]benzimidazol-6-one

Fremstillet analogt med Eksempel 1 fra l-etyl-5-iso-nikotionylamido-3-metyl-6-nitro-indolin-2-on. Prepared analogously to Example 1 from 1-ethyl-5-iso-nicothionylamido-3-methyl-6-nitro-indolin-2-one.

Utbytte: 39% av det teoretiske,Yield: 39% of the theoretical,

smeltepunkt: 264°C (etylacetat/isopropanol)melting point: 264°C (ethyl acetate/isopropanol)

C17<H>16N40 (292,34) C17<H>16N40 (292.34)

Beregnet: C, 69,85; H, 5,52; N, 19,17Calcd: C, 69.85; H, 5.52; N, 19,17

Funnet: C, 69,85; H, 5,61; N, 19,30 Found: C, 69.85; H, 5.61; N, 19.30

Eksempel 15 Example 15

5-metyl-2-(3-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]-benzimidazol- 6- on x 0, 5 H20 5-methyl-2-(3-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]-benzimidazol-6-one x 0.5 H2O

Fremstillet analogt med Eksempel 1 fra l-metyl-5-nikotinonylamido-6-nitro-indolin-2-on. Prepared analogously to Example 1 from 1-methyl-5-nicotinonylamido-6-nitro-indolin-2-one.

Utbytte: 58% av det teoretiske,Yield: 58% of the theoretical,

smeltepunkt: > 295°C (isopropanol/diisopropyleter)melting point: > 295°C (isopropanol/diisopropyl ether)

C15H12N40 x 0,5 H20 (273,29) C15H12N40 x 0.5 H2O (273.29)

Beregnet: C, 65,92; H, 4,79; N, 20,50Calcd: C, 65.92; H, 4.79; N, 20.50

Funnet: C, 65,95; H, 4,88; N, 20,72 Found: C, 65.95; H, 4.88; N, 20.72

Eksempel 16 Example 16

5-benzyl-7,7-dimetyl-2-(4-metoksyfenyl)-6,7-dihydro-3H,5H-pyrrolo[ 2, 3- f] benzimidazol- 6- on 5-benzyl-7,7-dimethyl-2-(4-methoxyphenyl)-6,7-dihydro-3H,5H-pyrrolo[ 2, 3- f ] benzimidazol- 6- one

Fremstillet analogt med Eksempel 1 fra l-benzyl-3,3-dimetyl-5-(4-metoksy-benzoylamido)-6-nitro-indolin-2-on. Utbytte: 68% av det teoretiske, Prepared analogously to Example 1 from 1-benzyl-3,3-dimethyl-5-(4-methoxy-benzoylamido)-6-nitro-indolin-2-one. Yield: 68% of the theoretical,

smeltepunkt: 298-300°C (isopropanol)melting point: 298-300°C (isopropanol)

C25<H>23<N>302(397 ,48) C25<H>23<N>302(397 .48)

Beregnet: C, 75,55; H, 5,83; N, 10,57Calculated: C, 75.55; H, 5.83; N, 10.57

Funnet: C, 75,74; H, 5,90; N, 10,57 Found: C, 75.74; H, 5.90; N, 10.57

Eksempel 17 Example 17

2-(2-fenyletyl)-5,7,7-trimetyl-6,7-dihydro-3H,5H-pyrrolo-[ 2, 3- f] benzimidazol- 6- on 2-(2-phenylethyl)-5,7,7-trimethyl-6,7-dihydro-3H,5H-pyrrolo-[2,3-f]benzimidazol-6-one

Fremstillet analogt med Eksempel 1 fra 6-nitro-5-(3-fenyl-propionamido)-1,3,3-trimetyl-indolin-2-on. Prepared analogously to Example 1 from 6-nitro-5-(3-phenyl-propionamido)-1,3,3-trimethyl-indolin-2-one.

Utbytte: 76% av det teoretiske,Yield: 76% of the theoretical,

smeltepunkt: fra 138°C (dekomp.; cykloheksan/etylacetat) C20<H>21N3O (319,41) melting point: from 138°C (decomp.; cyclohexane/ethyl acetate) C20<H>21N3O (319.41)

Beregnet: C, 75,21; H, 6,63; N, 13,16Calculated: C, 75.21; H, 6.63; N, 13,16

Funnet: C, 75,36; H, 6,87; N, 12,91 Found: C, 75.36; H, 6.87; N, 12.91

Eksempel 18 Example 18

2-benzyl-5,7,7-trimetyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]-benzimidazol- 6- on 2-benzyl-5,7,7-trimethyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]-benzimidazol-6-one

Fremstillet analogt med Eksempel 1 fra 6-nitro-5-fenyl-acetamido-1,3,3-trimetyl-indolin-2-on. Prepared analogously to Example 1 from 6-nitro-5-phenyl-acetamido-1,3,3-trimethyl-indolin-2-one.

Utbytte: 72% av det teoretiske,Yield: 72% of the theoretical,

smeltepunkt: 114-115°C (etylacetat/diisopropyleter) C19Hi<g>N30 (305,38) melting point: 114-115°C (ethyl acetate/diisopropyl ether) C19Hi<g>N30 (305.38)

Beregnet: C, 74,73; H, 6,27; N, 13,76Calculated: C, 74.73; H, 6.27; N, 13.76

Funnet: C, 74,55; H, 6,01; N, 13,95 Found: C, 74.55; H, 6.01; N, 13.95

Eksempel 19 Example 19

7,7-dimetyl-2-(4-hydroksyfenyl)-5-(2-pyridiniumetyl)-6,7-dihydro- 3H, 5H- pyrrolo[ 2, 3- f] benzimidazol- 6- on x 1, 5 H20 7,7-dimethyl-2-(4-hydroxyphenyl)-5-(2-pyridinedimethyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one x 1,5 H20

Fremstillet analogt med Eksempel 11 fra 7,7-dimetyl-5-(2-metoksyetyl)-2-(4-metoksyfenyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on og pyridin-hydroklorid. Prepared analogously to Example 11 from 7,7-dimethyl-5-(2-methoxyethyl)-2-(4-methoxyphenyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazole-6- on and pyridine hydrochloride.

Utbytte: 71% av det teoretiske,Yield: 71% of the theoretical,

smeltepunkt: > 300°C (vann)melting point: > 300°C (water)

C24H23C1N402x 1, 5 H20 (461,95) C24H23C1N402x 1.5H2O (461.95)

Beregnet: C, 62,40; H, 5,67; N, 12,13Calculated: C, 62.40; H, 5.67; N, 12,13

Funnet: C, 62,38; H, 5,50; N, 12,37 Found: C, 62.38; H, 5.50; N, 12.37

Eksempel 20 Example 20

7,7-dimetyl-5-isopropyl-2-(3-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[ 2, 3- f] benzimidazol- 6- on 7,7-dimethyl-5-isopropyl-2-(3-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one

Fremstillet analogt med Eksempel 1 fra 3,3-dimetyl-l-isopropyl-5-nikotinoylamido-6-nitro-indolin-2-on. Prepared analogously to Example 1 from 3,3-dimethyl-1-isopropyl-5-nicotinoylamido-6-nitro-indolin-2-one.

Utbytte: 37,6% av det teoretiske,Yield: 37.6% of the theoretical,

smeltepunkt: 224°C (etylacetat/diisopropyleter)melting point: 224°C (ethyl acetate/diisopropyl ether)

C19<H>20N40 (320,40) C19<H>20N40 (320.40)

Beregnet: C, 71,23; H, 6,29; N, 17,49Calculated: C, 71.23; H, 6.29; N, 17.49

Funnet: C, 71,05; H, 6,41; N, 17,37 Found: C, 71.05; H, 6.41; N, 17.37

Eksempel 21 Example 21

7,7-dimetyl-5-isopropyl-2-(4-metoksyfenyl)-6,7-dihydro-3H,5H-pyrrolo[ 2, 3- f] benzimidazol- 6- on 7,7-dimethyl-5-isopropyl-2-(4-methoxyphenyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one

Fremstillet analogt med Eksempel 1 fra 3,3-dimetyl-l-isopropyl-5-(4-metoksy-benzoylamido)-6-nitro-indolin-2-on. Utbytte: 66,5% av det teoretiske, Prepared analogously to Example 1 from 3,3-dimethyl-1-isopropyl-5-(4-methoxy-benzoylamido)-6-nitro-indolin-2-one. Yield: 66.5% of the theoretical,

smeltepunkt; > 290°C (etylacetat/isopropanol)melting point; > 290°C (ethyl acetate/isopropanol)

C21<H>23N302( 349,43 ) C21<H>23N302( 349.43 )

Beregnet: C, 72,18; H, 6,63; N, 12,03Calculated: C, 72.18; H, 6.63; N, 12.03

Funnet: C, 72,22; H, 6,72; N, 11,93 Found: C, 72.22; H, 6.72; N, 11.93

Eksempel 22 Example 22

7,7-dimetyl-5-n-pentyl-2-(3-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[ 2, 3- f] ben2imidazol- 6- on 7,7-dimethyl-5-n-pentyl-2-(3-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]ben2imidazol-6-one

Fremstillet analogt med Eksempel 1 fra 3,3-dimetyl-5-nikotinoylamido-6-nitro-l-n-pentyl-indolin-2-on. Prepared analogously to Example 1 from 3,3-dimethyl-5-nicotinoylamido-6-nitro-1-n-pentyl-indolin-2-one.

Utbytte: 50% av det teoretiske,Yield: 50% of the theoretical,

smeltepunkt: 177-178°C (etylacetat/diisopropyleter)melting point: 177-178°C (ethyl acetate/diisopropyl ether)

C21<H>24N40 (348,45) C21<H>24N40 (348.45)

Beregnet: C, 72,39; H, 6,94; N, 16,08Calculated: C, 72.39; H, 6.94; N, 16.08

Funnet: C, 72,31; H, 6,92; N, 15,96 Found: C, 72.31; H, 6.92; N, 15.96

Eksempel 23 Example 23

7,7-dimetyl-2-(4-metoksyfenyl)-5-n-pentyl-6,7-dihydro-3H,5H-pyrrolo[ 2, 3- f] benzimidazol- 6- on 7,7-Dimethyl-2-(4-methoxyphenyl)-5-n-pentyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one

Fremstillet analogt med Eksempel 1 fra 3,3-dimetyl-5-(4-metoksy-benzoylamido)-6-nitro-l-n-pentyl-indolin-2-on. Utbytte: 81% av det teoretiske, Prepared analogously to Example 1 from 3,3-dimethyl-5-(4-methoxy-benzoylamido)-6-nitro-1-n-pentyl-indolin-2-one. Yield: 81% of the theoretical,

smeltepunkt: 213-214°C (etylacetat)melting point: 213-214°C (ethyl acetate)

C23<H>27N3<0>2(477 ,49) C23<H>27N3<0>2(477 .49)

Beregnet: C, 73,18; H, 7,21; N, 11,13Calculated: C, 73.18; H, 7.21; N, 11,13

Funnet: C, 73,32; H, 7,26; N, 10,94 Found: C, 73.32; H, 7.26; N, 10.94

Eksempel 24 Example 24

7,7-dimetyl-5-isopropyl-2-(4-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[ 2, 3- f] benzimidazol- 6- on 7,7-Dimethyl-5-isopropyl-2-(4-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one

Fremstillet analogt med Eksempel 1 fra 3,3-dimetyl-5-isonikotinoylamido-l-isopropyl-6-nitro-indolin-2-on. Utbytte: 56% av det teoretiske, Prepared analogously to Example 1 from 3,3-dimethyl-5-isonicotinoylamido-1-isopropyl-6-nitro-indolin-2-one. Yield: 56% of the theoretical,

smeltepunkt: 276-277°C (etylacetat/diisopropyleter) Cig<H>20N4O (320,40) melting point: 276-277°C (ethyl acetate/diisopropyl ether) Cig<H>20N4O (320.40)

Beregnet: C, 71,23; H, 6,29; N, 17,49Calculated: C, 71.23; H, 6.29; N, 17.49

Funnet: C, 71,18; H, 6,28; N, 17,30 Found: C, 71.18; H, 6.28; N, 17.30

Eksempel 25 Example 25

7,7-dimetyl-5-n-pentyl-2-(4-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[ 2, 3- f] benzimidazol- 6- on 7,7-Dimethyl-5-n-pentyl-2-(4-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one

Fremstillet analogt med Eksempel 1 fra 3,3-dimetyl-5-isonikotinoylamido-6-nitro-l-n-pentyl-indolin-2-on. Prepared analogously to Example 1 from 3,3-dimethyl-5-isonicotinoylamido-6-nitro-1-n-pentyl-indolin-2-one.

Utbytte: 78% av det teoretiske,Yield: 78% of the theoretical,

smeltepunkt: 105-106°C (etylacetat/diisopropyleter)melting point: 105-106°C (ethyl acetate/diisopropyl ether)

C21<H>24N40 (348,45) C21<H>24N40 (348.45)

Beregnet: C, 72,39; H, 6,94; N, 16,08Calculated: C, 72.39; H, 6.94; N, 16.08

Funnet: C, 72,39; H, 6,90; N, 15,92 Found: C, 72.39; H, 6.90; N, 15.92

Eksempel 26 Example 26

5-etyl-2-(3,5-di-tert-butyl-4-hydroksy-fenyl)-7,7-dimetyl-6,7-dihydro- 3H, 5H- pyrrolo[ 2, 3- f] benzimidazol- 6- on 5-ethyl-2-(3,5-di-tert-butyl-4-hydroxy-phenyl)-7,7-dimethyl-6,7-dihydro- 3H, 5H- pyrrolo[ 2, 3- f ] benzimidazole- 6- Wed

Fremstillet analogt med Eksempel 1 fra l-etyl-5-(3,5-di-tert-butyl-4-hydroksy-benzoylamido)-3,3-dimetyl-6-nitro-indolin-2-on. Prepared analogously to Example 1 from 1-ethyl-5-(3,5-di-tert-butyl-4-hydroxy-benzoylamido)-3,3-dimethyl-6-nitro-indolin-2-one.

Utbytte: 40% av det teoretiske,Yield: 40% of the theoretical,

smeltepunkt: > 300°C (etylacetat/diisopropyleter)melting point: > 300°C (ethyl acetate/diisopropyl ether)

C27<H>35N3<0>2(433 , 59) C27<H>35N3<0>2(433 , 59)

Beregnet: C, 74,79; H, 8,14; N, 9,69Calculated: C, 74.79; H, 8.14; N, 9.69

Funnet: C, 74,73; H, 8,33; N, 9,50 Found: C, 74.73; H, 8.33; N, 9.50

Eksempel 27 Example 27

5-n-butyl-7,7-dimetyl-2-(3-pyridyl)-6,7-dihydro-3H,5H-pyrrolo-[ 2 , 3- f ] benzimidazol- 6- on 5-n-butyl-7,7-dimethyl-2-(3-pyridyl)-6,7-dihydro-3H,5H-pyrrolo-[2,3-f]benzimidazol-6-one

Fremstillet analogt med Eksempel 1 fra l-n-butyl-3,3-dimetyl-5-nikotinoylamido-6-nitro-indolin-2-on. Prepared analogously to Example 1 from 1-n-butyl-3,3-dimethyl-5-nicotinoylamido-6-nitro-indolin-2-one.

Utbytte: 64% av det teoretiske,Yield: 64% of the theoretical,

smeltepunkt: 175-176°C (etylacetat/diisopropyleter)melting point: 175-176°C (ethyl acetate/diisopropyl ether)

C20<H>22N40 (334,42) C20<H>22N40 (334.42)

Beregnet: C, 71,83; H, 6,63; N, 16,75Calculated: C, 71.83; H, 6.63; N, 16.75

Funnet: C, 71,93; H, 6,67; N, 16,82 Found: C, 71.93; H, 6.67; N, 16.82

Eksempel 28 Example 28

7,7-dimetyl-2-(4-metoksyfenyl)-5-n-propyl-6,7-dihydro-3H,5H-pyrrolo[ 2, 3- f] benzimidazol- 6- on 7,7-Dimethyl-2-(4-methoxyphenyl)-5-n-propyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one

Fremstillet analogt med Eksempel 1 fra 3,3-dimetyl-5-(4-metoksy-benzoylamido)-6-nitro-1-n-propyl-indolin-2-on. Utbytte: 74% av det teoretiske, Prepared analogously to Example 1 from 3,3-dimethyl-5-(4-methoxy-benzoylamido)-6-nitro-1-n-propyl-indolin-2-one. Yield: 74% of the theoretical,

smeltepunkt: 262-263°C (etylacetat/diisopropyleter) C21<H>23N302(349,43) melting point: 262-263°C (ethyl acetate/diisopropyl ether) C21<H>23N3O2(349.43)

Beregnet: C, 72,18; H, 6,63; N, 12,03Calculated: C, 72.18; H, 6.63; N, 12.03

Funnet: C, 72,03; H, 6,69; N, 11,99 Found: C, 72.03; H, 6.69; N, 11.99

Eksempel 29 Example 29

5-n-butyl-7,7-dimetyl-2-(4-metoksyfenyl)-6,7-dihydro-3H,5H-pyrrolo[ 2, 3- f] benzimidazol- 6- on 5-n-butyl-7,7-dimethyl-2-(4-methoxyphenyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one

Fremstillet analogt med Eksempel 1 fra l-n-butyl-3,3-dimetyl-5-(4-metoksy-benzoylamido)-6-nitro-indolin-2-on. Utbytte: 70% av det teoretiske, Prepared analogously to Example 1 from 1-n-butyl-3,3-dimethyl-5-(4-methoxy-benzoylamido)-6-nitro-indolin-2-one. Yield: 70% of the theoretical,

smeltepunkt: 227-228°C (etylacetat/diisopropyleter) C22<H>25N302(363 ,46) melting point: 227-228°C (ethyl acetate/diisopropyl ether) C22<H>25N3O2(363 .46)

Beregnet: C, 72,70; H, 6,93; N, 11,56Calculated: C, 72.70; H, 6.93; N, 11.56

Funnet: C, 72,83; H, 7,04; N, 11,52 Found: C, 72.83; H, 7.04; N, 11.52

Eksempel 30 Example 30

5-n-butyl-7,7-dimetyl-2-(4-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[ 2, 3- f] benzimidazol- 6- on 5-n-butyl-7,7-dimethyl-2-(4-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one

Fremstillet analogt med Eksempel 1 fra l-n-butyl-3,3-dimetyl-5-isonikotinoylamido-6-nitro-indolin-2-on. Prepared analogously to Example 1 from 1-n-butyl-3,3-dimethyl-5-isonicotinoylamido-6-nitro-indolin-2-one.

Utbytte: 67% av det teoretiske,Yield: 67% of the theoretical,

smeltepunkt: 127-129°C (etylacetat/diisopropyleter)melting point: 127-129°C (ethyl acetate/diisopropyl ether)

C20<H>22N40 (334,42) C20<H>22N40 (334.42)

Beregnet: C, 71,83; H, 6,63; N, 16,75Calculated: C, 71.83; H, 6.63; N, 16.75

Funnet: C, 71,70; H, 6,84; N, 16,62 Found: C, 71.70; H, 6.84; N, 16.62

Eksempel 31 Example 31

5- etyl-7,7-dimetyl-2-(3-tienyl) -6,7-dihydro-3H,5H-pyrrolo-[ 2, 3- f] benzimidazol- 6- on 5- ethyl-7,7-dimethyl-2-(3-thienyl)-6,7-dihydro-3H,5H-pyrrolo-[2,3-f]benzimidazol-6-one

Fremstillet analogt med Eksempel 1 fra l-etyl-3,3-dimetyl-6- nitro-5-(3-tenoylamido)-indolin-2-on. Prepared analogously to Example 1 from 1-ethyl-3,3-dimethyl-6-nitro-5-(3-thenoylamido)-indolin-2-one.

Utbytte: 52% av det teoretiske,Yield: 52% of the theoretical,

smeltepunkt: > 295°C (etylacetat/isopropanol)melting point: > 295°C (ethyl acetate/isopropanol)

C17<H>17N3OS (311,41) C17<H>17N3OS (311.41)

Beregnet: C, 65,57; H, 5,50; N, 13,49; S, 10,30 Funnet: C, 65,70; H, 5,43; N, 13,38; S, 10,49 Calculated: C, 65.57; H, 5.50; N, 13.49; S, 10.30 Found: C, 65.70; H, 5.43; N, 13.38; S, 10.49

Eksempel 32 Example 32

5-etyl-7,7-dimetyl-2-(3-furyl)-6,7-dihydro-3H,5H-pyrrolo-[ 2, 3- f] benzimidazol- 6- on 5-ethyl-7,7-dimethyl-2-(3-furyl)-6,7-dihydro-3H,5H-pyrrolo-[2,3-f]benzimidazol-6-one

Fremstillet analogt med Eksempel 1 fra l-etyl-3,3-dimetyl-5-(3-furoylamido)-6-nitro-indolin-2-on. Prepared analogously to Example 1 from 1-ethyl-3,3-dimethyl-5-(3-furoylamido)-6-nitro-indolin-2-one.

Utbytte: 65,2% av det teoretiske,Yield: 65.2% of the theoretical,

smeltepunkt: 267-269°C (etylacetat/diisopropyleter) C17<H>17N3<0>2(295,34) melting point: 267-269°C (ethyl acetate/diisopropyl ether) C17<H>17N3<0>2(295.34)

Beregnet: C, 69,14; H, 5,80; N, 14,23Calculated: C, 69.14; H, 5.80; N, 14.23

Funnet: C, 69,23; H, 5,91; N, 14,13 Found: C, 69.23; H, 5.91; N, 14,13

Eksempel 33 Example 33

7,7-dimetyl-2-(3-furyl)-5-isopropyl-6,7-dihydro-3H,5H-pyrrolo[ 2 , 3- f ] benzimidazol- 6- on 7,7-dimethyl-2-(3-furyl)-5-isopropyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one

Fremstillet analogt med Eksempel 1 fra 3,3-dimetyl-5-(3-furoylamido)-l-isopropyl-6-nitro-indolin-2-on. Prepared analogously to Example 1 from 3,3-dimethyl-5-(3-furoylamido)-1-isopropyl-6-nitro-indolin-2-one.

Utbytte: 56% av det teoretiske,Yield: 56% of the theoretical,

smeltepunkt: 282-284°C (isopropanol/etylacetat)melting point: 282-284°C (isopropanol/ethyl acetate)

C18<H>19N302(309, 37 ) C18<H>19N302(309, 37 )

Beregnet: C, 69,88; H, 6,19; N, 13,58Calcd: C, 69.88; H, 6.19; N, 13.58

Funnet: C, 69,66; H, 6,25; N, 13,31 Found: C, 69.66; H, 6.25; N, 13.31

Eksempel 34 Example 34

7,7-dimetyl-2-(3-furyl)-5-n-pentyl-6,7-dihydro-3H,5H-pyrrolo-[ 2, 3- f] benzimidazol- 6- on 7,7-Dimethyl-2-(3-furyl)-5-n-pentyl-6,7-dihydro-3H,5H-pyrrolo-[2,3-f]benzimidazol-6-one

Fremstillet analogt med Eksempel 1 fra 3,3-dimetyl-5-(3-furoylamido)-6-nitro-l-n-pentyl-indolin-2-on. Prepared analogously to Example 1 from 3,3-dimethyl-5-(3-furoylamido)-6-nitro-1-n-pentyl-indolin-2-one.

Utbytte: 70,4% av det teoretiske,Yield: 70.4% of the theoretical,

smeltepunkt: 198°C (etylacetat/diisopropyleter)melting point: 198°C (ethyl acetate/diisopropyl ether)

C20<H>23<N>302(337 ,42) C20<H>23<N>302(337 .42)

Beregnet: C, 70,37; H, 6,98; N, 11,84Calculated: C, 70.37; H, 6.98; N, 11.84

Funnet: C, 70,25; H, 7,17; N, 11,99 Found: C, 70.25; H, 7.17; N, 11.99

Eksempel 35 Example 35

5-etyl-2-(4-amino-3,5-dibromfenyl)-7,7-dimetyl-6,7-dihydro-3H, 5Hpyrrolo[ 2, 3- f] benzimidazol- 6- on 5-ethyl-2-(4-amino-3,5-dibromophenyl)-7,7-dimethyl-6,7-dihydro-3H,5Hpyrrolo[2,3-f]benzimidazol-6-one

Fremstillet analogt med Eksempel 1 fra l-etyl-5-(4-amino-3,5-dibrom-benzoylamido)-3,3-dimety1-6-nitro-indolin-2-on. Utbytte: 28% av det teoretiske, Prepared analogously to Example 1 from 1-ethyl-5-(4-amino-3,5-dibromo-benzoylamido)-3,3-dimethyl-6-nitro-indolin-2-one. Yield: 28% of the theoretical,

smeltepunkt: > 300°C (etylacetat/eter)melting point: > 300°C (ethyl acetate/ether)

C19H18Br2N40 (478,21) C19H18Br2N40 (478.21)

Beregnet: C, 47,72; H, 3,79; N, 11,72; Br, 33,42 Calculated: C, 47.72; H, 3.79; N, 11.72; Br, 33,42

Funnet: C, 47,54; H, 3,86; N, 11,58; Br, 33,46 Found: C, 47.54; H, 3.86; N, 11.58; Br, 33,46

Eksempel 36 Example 36

7,7-dimetyl-5-n-propyl-2-(3-pyridyl) - 6,7-dihydro-3H,5H-pyrrolo[ 2, 3- f] benzimidazol- 6- on x 0, 5 H20 7,7-dimethyl-5-n-propyl-2-(3-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one x 0.5 H20

Fremstillet analogt med Eksempel 1 fra 3,3-dimetyl-5-nikotinoylamido-6-nitro-1-n-propyl-indolin-2-on. Prepared analogously to Example 1 from 3,3-dimethyl-5-nicotinoylamido-6-nitro-1-n-propyl-indolin-2-one.

Utbytte: 54% av det teoretiske,Yield: 54% of the theoretical,

smeltepunkt: fra 145°C (dekomp.: etylacetat/diisopropyleter) ClgH20N40 x 0,5 H20 (329,40) melting point: from 145°C (decomp.: ethyl acetate/diisopropyl ether) ClgH20N40 x 0.5 H20 (329.40)

Beregnet: C, 69,28; H, 6,42; N, 17,01Calculated: C, 69.28; H, 6.42; N, 17.01

Funnet: C, 69,38; H, 6,40; N, 17,26 Found: C, 69.38; H, 6.40; N, 17,26

Eksempel 37 Example 37

7,7-dimetyl-5-n-propyl-2-(4-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[ 2, 3- f] ben2imidazol- 6- on 7,7-Dimethyl-5-n-propyl-2-(4-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]ben2imidazol-6-one

Fremstillet analogt med Eksempel 1 fra 3,3-dimetyl-5-isonikotinoylamido-6-nitro-1-n-propyl-indolin-2-on. Utbytte: 58% av det teoretiske, Prepared analogously to Example 1 from 3,3-dimethyl-5-isonicotinoylamido-6-nitro-1-n-propyl-indolin-2-one. Yield: 58% of the theoretical,

smeltepunkt: > 295°C (etylacetat/diisopropyleter)melting point: > 295°C (ethyl acetate/diisopropyl ether)

C19<H>20N40 (320,40) C19<H>20N40 (320.40)

Beregnet: C, 71,23; H, 6,29; N, 17,49Calculated: C, 71.23; H, 6.29; N, 17.49

Funnet: C, 71,15; H, 6,49; N, 17,60 Found: C, 71.15; H, 6.49; N, 17.60

Eksempel 38 Example 38

7,7-dimetyl-2-(3-furyl)-5-(2-metoksyetyl)-6,7-dihydro-3H,5H-pyrrolo[ 2, 3- f] benzimidazol- 6- on 7,7-dimethyl-2-(3-furyl)-5-(2-methoxyethyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one

Fremstillet analogt med Eksempel 1 fra 3,3-dimetyl-5-(3-furoylamido)-1-(2-metoksyetyl)-6-nitro-indolin-2-on. Utbytte: 66,5% av det teoretiske, Prepared analogously to Example 1 from 3,3-dimethyl-5-(3-furoylamido)-1-(2-methoxyethyl)-6-nitro-indolin-2-one. Yield: 66.5% of the theoretical,

smeltepunkt: 226-227°C (etylacetat/diisopropyleter) C16<H>19N3<0>3(325,37 ) melting point: 226-227°C (ethyl acetate/diisopropyl ether) C16<H>19N3<0>3(325.37 )

Beregnet: C, 66,45; H, 5,89; N, 12,91Calcd: C, 66.45; H, 5.89; N, 12.91

Funnet: C, 66,45; H, 5,96; N, 12,70 Found: C, 66.45; H, 5.96; N, 12.70

Eksempel 39 Example 39

7,7-dimetyl-5-isopropyl-2-(3-tienyl)-6,7-dihydro-3H,5H-pyrrolo [ 2 , 3- f ] benzimidazol- 6- on 7,7-dimethyl-5-isopropyl-2-(3-thienyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one

Fremstillet analogt med Eksempel 1 fra 3,3-dimetyl-l-isopropyl-6-nitro-5-(3-tenoylamido)-indolin-2-on. Prepared analogously to Example 1 from 3,3-dimethyl-1-isopropyl-6-nitro-5-(3-thenoylamido)-indolin-2-one.

Utbytte: 70,5% av det teoretiske,Yield: 70.5% of the theoretical,

smeltepunkt: > 300°C (etylacetat/isopropanol)melting point: > 300°C (ethyl acetate/isopropanol)

C18<H>19N30S ( 325 ,43 ) C18<H>19N30S ( 325 .43 )

Beregnet: C, 66,43; H, 5,88; N, 12,91; S, 9,85 Calculated: C, 66.43; H, 5.88; N, 12.91; S, 9.85

Funnet: C, 66,54; H, 6,07; N, 12,70; S, 9,66 Found: C, 66.54; H, 6.07; N, 12.70; S, 9.66

Eksempel 40 Example 40

7,7-dimetyl-5-n-pentyl-2-(3-tienyl) -6,7-dihydro-3H,5H-pyrrolo[ 2 , 3- f ] benzimidazol- 6- on 7,7-dimethyl-5-n-pentyl-2-(3-thienyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one

Fremstillet analogt med Eksempel 1 fra 3,3-dimetyl-l-n-penty1-6-nitro-5-(3-tenoylamido)-indolin-2-on. Prepared analogously to Example 1 from 3,3-dimethyl-1-n-pentyl-6-nitro-5-(3-thenoylamido)-indolin-2-one.

Utbytte: 56,6% av det teoretiske,Yield: 56.6% of the theoretical,

smeltepunkt: 163-164°C (etylacetat/diisopropyleter)melting point: 163-164°C (ethyl acetate/diisopropyl ether)

C20<H>23N30S (353,48) C20<H>23N30S (353.48)

Beregnet: C, 67,98; H, 6,56; N, 11,89; S, 9,07 Calculated: C, 67.98; H, 6.56; N, 11.89; S, 9.07

Funnet: C, 67,76; H, 6,72; N, 11,68; S, 8,88 Found: C, 67.76; H, 6.72; N, 11.68; S, 8.88

Eksempel 41 Example 41

7,7-dimetyl-5-(2-metoksyetyl)-2-(3-tienyl)-6,7-dihydro-3H,5H-pyrrolo[ 2, 3- f] benzimidazol- 6- on 7,7-dimethyl-5-(2-methoxyethyl)-2-(3-thienyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one

Fremstillet analogt med Eksempel 1 fra 3,3-dimetyl-l-(2-metoksyetyl)-6-nitro-5-(3-tenoylamido)-indolin-2-on. Utbytte: 57,6% av det teoretiske, Prepared analogously to Example 1 from 3,3-dimethyl-1-(2-methoxyethyl)-6-nitro-5-(3-thenoylamido)-indolin-2-one. Yield: 57.6% of the theoretical,

smeltepunkt: 260-261°C (etylacetat/diisopropyleter) C18<H>19<N>302S (341,43) melting point: 260-261°C (ethyl acetate/diisopropyl ether) C18<H>19<N>302S (341.43)

Beregnet: C, 63,32; H, 5,61; N, 12,31; S, 9,39 Calculated: C, 63.32; H, 5.61; N, 12.31; S, 9.39

Funnet: C, 63,51; H, 5,74; N, 12,10; S, 9,19 Found: C, 63.51; H, 5.74; N, 12.10; S, 9,19

Eksempel 42 Example 42

5- etyl-7,7-dimetyl-2-(2-pyrazinyl)-6,7-dihydro-3H,5H-pyrrolo-[ 2, 3- f] benzimidazol- 6- on x 0, 5 H20 5- ethyl-7,7-dimethyl-2-(2-pyrazinyl)-6,7-dihydro-3H,5H-pyrrolo-[2,3-f]benzimidazol-6-one x 0.5 H20

Fremstillet analogt med Eksempel 1 fra l-etyl-3,3-dimetyl-6- nitro-5-(2-pyrazinoylamido)-indolin-2-on. Prepared analogously to Example 1 from 1-ethyl-3,3-dimethyl-6-nitro-5-(2-pyrazinoylamido)-indolin-2-one.

Utbytte: 22,8% av det teoretiske,Yield: 22.8% of the theoretical,

smeltepunkt: > 290°Cmelting point: > 290°C

C17H17N50 x 0,5 H20 (316,36) C17H17N50 x 0.5 H2O (316.36)

Beregnet: C, 64,54; H, 5,73; N, 22,14Calculated: C, 64.54; H, 5.73; N, 22.14

Funnet: C, 64,68; H, 5,87; N, 22,38 Found: C, 64.68; H, 5.87; N, 22.38

Eksempel 43 Example 43

5-etyl-7,7-dimetyl-2-(2-furyl)-6,7-dihydro-3H,5H-pyrrolo-[ 2 , 3- f ] benzimidazol- 6- on 5-ethyl-7,7-dimethyl-2-(2-furyl)-6,7-dihydro-3H,5H-pyrrolo-[2,3-f]benzimidazol-6-one

Fremstillet analogt med Eksempel 1 fra l-etyl-3,3-dimetyl-5-(2-furoylamido)-6-nitro-indolin-2-on. Prepared analogously to Example 1 from 1-ethyl-3,3-dimethyl-5-(2-furoylamido)-6-nitro-indolin-2-one.

Utbytte: 44,3% av det teoretiske,Yield: 44.3% of the theoretical,

smeltepunkt: > 290°Cmelting point: > 290°C

C17<H>17<N>302(295 , 34) C17<H>17<N>302(295 , 34)

Beregnet: C, 69,14; H, 5,80; N, 14,23Calculated: C, 69.14; H, 5.80; N, 14.23

Funnet: C, 68,95; H, 5,90; N, 14,50 Found: C, 68.95; H, 5.90; N, 14.50

Eksempel 44 Example 44

5- etyl-7,7-dimetyl-2-(2-tienyl)-6,7-dihydro-3H,5H-pyrrolo-[ 2 , 3- f ] benzimidazol- 6- on 5-ethyl-7,7-dimethyl-2-(2-thienyl)-6,7-dihydro-3H,5H-pyrrolo-[2,3-f]benzimidazol-6-one

Fremstillet analogt med Eksempel 1 fra l-etyl-3,3-dimetyl-6- nitro-5-(2-tenoylamido)-indolin-2-on. Prepared analogously to Example 1 from 1-ethyl-3,3-dimethyl-6-nitro-5-(2-thenoylamido)-indolin-2-one.

Utbytte: 67,6% av det teoretiske,Yield: 67.6% of the theoretical,

smeltepunkt: > 290°C (isopropanol)melting point: > 290°C (isopropanol)

C17<H>17N30S (311,41) C17<H>17N30S (311.41)

Beregnet: C, 65,57; H, 5,50; N, 13,49Calculated: C, 65.57; H, 5.50; N, 13.49

Funnet: C, 65,48; H, 5,59; N, 13,60 Found: C, 65.48; H, 5.59; N, 13.60

Eksempel 45 Example 45

5-etyl-7,7-dimetyl-2-(4-metylmerkaptofenyl)-6,7-dihydro-3H,5H-pyrrolo[ 2, 3- f] benzimidazol- 6- on 5-ethyl-7,7-dimethyl-2-(4-methylmercaptophenyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one

Fremstillet analogt med Eksempel 1 fra l-etyl-3,3-dimetyl-5-(4-metylmerkapto-benzoylamido)-6-nitro-indolin-2-on. Utbytte: 70,5% av det teoretiske, Prepared analogously to Example 1 from 1-ethyl-3,3-dimethyl-5-(4-methylmercapto-benzoylamido)-6-nitro-indolin-2-one. Yield: 70.5% of the theoretical,

smeltepunkt: 293°Cmelting point: 293°C

C20<H>21N3OS (351,47 ) C20<H>21N3OS (351.47 )

Beregnet: C, 68,35; H, 6,02; N, 11,96Calcd: C, 68.35; H, 6.02; N, 11.96

Funnet: C, 68,21; H, 6,15; N, 11,96 Found: C, 68.21; H, 6.15; N, 11.96

Eksempel 46 Example 46

5-etyl-7,7-dimetyl-2-(4-dimetylaminofenyl)-6,7-dihydro-3H,5H-pyrrolo[ 2 , 3- f ] benzimidazol- 6- on 5-ethyl-7,7-dimethyl-2-(4-dimethylaminophenyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one

Fremstillet analogt med Eksempel 1 fra l-etyl-3,3-dimetyl-5-(4-dimetylamino-benzoylamido)-6-nitro-indolin-2-on. Prepared analogously to Example 1 from 1-ethyl-3,3-dimethyl-5-(4-dimethylamino-benzoylamido)-6-nitro-indolin-2-one.

Utbytte: 49,8% av det teoretiske,Yield: 49.8% of the theoretical,

smeltepunkt: 287°Cmelting point: 287°C

C21<H>24N40 (348,45) C21<H>24N40 (348.45)

Beregnet: C, 72,39; H, 6,94; N, 16,08Calculated: C, 72.39; H, 6.94; N, 16.08

Funnet: C, 72,19; H, 7,00; N, 16,00 Found: C, 72.19; H, 7.00; Thu, 16.00

Eksempel 47 Example 47

5-etyl-7,7-dimetyl-2-(2-metoksy-4-metylmerkaptofenyl) -6,7-dihydro- 3H, 5H- pyrrolo[ 2, 3- f] benzimidazol- 6- on 5-ethyl-7,7-dimethyl-2-(2-methoxy-4-methylmercaptophenyl)-6,7-dihydro- 3H , 5H - pyrrolo[ 2, 3- f ] benzimidazol- 6- one

Fremstillet analogt med Eksempel 1 fra l-etyl-3,3-dimetyl-5-(2-metoksy-4-metylmerkapto-benzoylamido)-6-nitro-indolin-2-on. Utbytte: 64,5% av det teoretiske, Prepared analogously to Example 1 from 1-ethyl-3,3-dimethyl-5-(2-methoxy-4-methylmercapto-benzoylamido)-6-nitro-indolin-2-one. Yield: 64.5% of the theoretical,

smeltepunkt: 220°Cmelting point: 220°C

C21<H>23N302S (381,50) C21<H>23N302S (381.50)

Beregnet: C, 66,12; H, 6,08; N, 11,01Calculated: C, 66.12; H, 6.08; N, 11.01

Funnet: C, 65,98; H, 6,11; N, 11,02 Found: C, 65.98; H, 6.11; N, 11.02

Eksempel 48 Example 48

5-etyl-2-(2-kinolyl)-7,7-dimetyl-6,7-dihydro-3H,5H-pyrrolo-[ 2 , 3- f ] benzimidazol- 6- on x 2, 5 H20 5-ethyl-2-(2-quinolyl)-7,7-dimethyl-6,7-dihydro-3H,5H-pyrrolo-[2,3-f]benzimidazol-6-one x 2,5H2O

Fremstillet analogt med Eksempel 1 fra l-etyl-5-(2-kinolin-karbonamido)-3,3-dimetyl-6-nitro-indolin-2-on. Prepared analogously to Example 1 from 1-ethyl-5-(2-quinoline-carbonamido)-3,3-dimethyl-6-nitro-indolin-2-one.

Utbytte: 28,2% av det teoretiske,Yield: 28.2% of the theoretical,

smeltepunkt: 280°Cmelting point: 280°C

C22<H>20N4O (356,43 ) C22<H>20N4O (356.43 )

Beregnet: C, 65,82; H, 6,28; N, 13,96 Funnet: C, 65,98; H, 6,03; N, 13,77 Calculated: C, 65.82; H, 6.28; N, 13.96 Found: C, 65.98; H, 6.03; N, 13.77

Eksempel 49 Example 49

5-etyl-2-(4-aminofenyl)-7,7-dimetyl-6,7-dihydro-3H,5H-pyrrolo-[ 2, 3- f] benzimidazol- 6- on 5-ethyl-2-(4-aminophenyl)-7,7-dimethyl-6,7-dihydro-3H,5H-pyrrolo-[2,3-f]benzimidazol-6-one

Fremstillet analogt med Eksempel 1 fra l-etyl-5-(4-amino-benzoylamido)-3,3-dimety1-6-nitro-indolin-2-on. Prepared analogously to Example 1 from 1-ethyl-5-(4-amino-benzoylamido)-3,3-dimethyl-6-nitro-indolin-2-one.

Utbytte: 55,7% av det teoretiske,Yield: 55.7% of the theoretical,

smeltepunkt: > 295°C (metanol/isopropanol)melting point: > 295°C (methanol/isopropanol)

C19<H>20N40 (320,40) C19<H>20N40 (320.40)

Beregnet: C, 71,23; H, 6,29; N, 17,49Calculated: C, 71.23; H, 6.29; N, 17.49

Funnet: C, 71,18; H, 6,48; N, 17,37 Found: C, 71.18; H, 6.48; N, 17.37

Eksempel 50 Example 50

2-(l-acetyl-4-piperidinyl)-5-etyl-7,7-dimetyl-6,7-dihydro-3H, 5H- pyrrolo[ 2, 3- f] benzimidazol- 6- on 2-(1-Acetyl-4-piperidinyl)-5-ethyl-7,7-dimethyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one

Fremstillet analogt med Eksempel 1 fra 5-(l-acetyl-4-piperidinkarbonamido)-l-etyl-3,3-dimetyl-6-nitro-indolin-2-on. Utbytte: 58,8% av det teoretiske, Prepared analogously to Example 1 from 5-(1-acetyl-4-piperidinecarbonamido)-1-ethyl-3,3-dimethyl-6-nitro-indolin-2-one. Yield: 58.8% of the theoretical,

smeltepunkt: 258°Cmelting point: 258°C

C20<H>26N402(354,45 ) C20<H>26N402(354.45 )

Beregnet: C, 67,77; H, 7,39; N, 15,81Calculated: C, 67.77; H, 7.39; N, 15.81

Funnet: C, 67,90; H, 7,52; N, 16,05 Found: C, 67.90; H, 7.52; N, 16.05

Eksempel 51 Example 51

5-etyl-2-(4-klorfenyl)-7,7-dimetyl-6,7-dihydro-3H,5H-pyrrolo-[ 2 , 3- f ] benzimidazol- 6- on 5-ethyl-2-(4-chlorophenyl)-7,7-dimethyl-6,7-dihydro-3H,5H-pyrrolo-[2,3-f]benzimidazol-6-one

Fremstillet analogt med Eksempel 1 fra l-etyl-5-(4-klor-benzoylamido)-3,3-dimetyl-6-nitro-indolin-2-on. Prepared analogously to Example 1 from 1-ethyl-5-(4-chloro-benzoylamido)-3,3-dimethyl-6-nitro-indolin-2-one.

Utbytte: 79% av det teoretiske,Yield: 79% of the theoretical,

smeltepunkt: 291°Cmelting point: 291°C

C19H18C1N30 (339,83) C19H18C1N30 (339.83)

Beregnet: C, 67,15; H, 5,34; N, 12,37Calculated: C, 67.15; H, 5.34; N, 12.37

Funnet: C, 67,30; H, 5,41; N, 12,37 Found: C, 67.30; H, 5.41; N, 12.37

Eksempel 52 Example 52

5-etyl-2-(1,2,3,4-tetrahydro-4-kinolyl)-7,7-dimetyl-6,7-dihydro- 3H, 5H- pyrrolo[ 2, 3- f] benzimidazol- 6- on- dihydroklorid 5-ethyl-2-(1,2,3,4-tetrahydro-4-quinolyl)-7,7-dimethyl-6,7-dihydro- 3H, 5H- pyrrolo[ 2, 3- f ] benzimidazole- 6- on- dihydrochloride

Fremstillet analogt med Eksempel 1 fra l-etyl-5-(4-kinolinkarbonamido)-3,3-dimetyl-6-nitro-indolin-2-on. Utbytte: 45,3% av det teoretiske, Prepared analogously to Example 1 from 1-ethyl-5-(4-quinolinecarbonamido)-3,3-dimethyl-6-nitro-indolin-2-one. Yield: 45.3% of the theoretical,

smeltepunkt: 248-250°Cmelting point: 248-250°C

C22H26C12N40 (433,39) C22H26C12N40 (433.39)

Beregnet: C, 60,97; K, 6,05; N, 12,93Calcd: C, 60.97; K, 6.05; N, 12.93

Funnet: C, 61,14; H, 6,23; N, 13,16 Found: C, 61.14; H, 6.23; N, 13,16

Eksempel 53 Example 53

5-etyl-2-(4-kinolyl)-7,7-dimetyl-6,7-dihydro-3H,5H-pyrrolo-[ 2, 3- f] benzimidazol- 6- on 5-ethyl-2-(4-quinolyl)-7,7-dimethyl-6,7-dihydro-3H,5H-pyrrolo-[2,3-f]benzimidazol-6-one

Fremstillet analogt med Eksempel 1 fra l-etyl-5-(4-kinolin-karbonamido)-3,3-dimety1-6-nitro-indolin-2-on. Utbytte: 18,3% av det teoretiske, Prepared analogously to Example 1 from 1-ethyl-5-(4-quinoline-carbonamido)-3,3-dimethyl-6-nitro-indolin-2-one. Yield: 18.3% of the theoretical,

smeltepunkt: 278°Cmelting point: 278°C

C22H20N40 (356,43) C22H20N40 (356.43)

Beregnet: C, 74,14; H, 5,66; N, 15,72Calculated: C, 74.14; H, 5.66; N, 15.72

Funnet: C, 73,97; H, 5,56; N, 15,72 Found: C, 73.97; H, 5.56; N, 15.72

Eksempel 54 Example 54

5-etyl-2-(5,6,7,8-tetrahydro-4-kinolyl)-7,7-dimetyl-6,7-dihydro- 3H, 5H- pyrrolo[ 2, 3- f] benzimidazol- 6- on- hydroklorid 5-ethyl-2-(5,6,7,8-tetrahydro-4-quinolyl)-7,7-dimethyl-6,7-dihydro- 3H, 5H- pyrrolo[ 2, 3- f ] benzimidazole- 6- on- hydrochloride

Fremstillet analogt med Eksempel 1 fra l-etyl-5-(4-kinolin-karbonamido)-3,3-dimetyl-6-nitro-indolin-2-on. Utbytte: 15% av det teoretiske, Prepared analogously to Example 1 from 1-ethyl-5-(4-quinoline-carbonamido)-3,3-dimethyl-6-nitro-indolin-2-one. Yield: 15% of the theoretical,

smeltepunkt: 150°C (dekomp.)melting point: 150°C (decomp.)

C22H25C1N40 (396,92) C22H25C1N40 (396.92)

Beregnet: C, 66,57; H, 6,35; N, 14,12Calculated: C, 66.57; H, 6.35; N, 14,12

Funnet: C, 66,39; H, 6,45; N, 13,92 Found: C, 66.39; H, 6.45; N, 13.92

Eksempel 55 Example 55

5-etyl-7,7-dimetyl-2-(2-dimetylamino-3-pyridyl) - 6,7-dihydro-3H, 5H- pyrrolo[ 2, 3- f] ben2imidazol- 6- on- dihydroklorid x H20 5-ethyl-7,7-dimethyl-2-(2-dimethylamino-3-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]ben2imidazol-6-one-dihydrochloride x H20

Fremstillet analogt med Eksempel 1 fra l-etyl-3,3-dimetyl-5-(2-dimetylamino-nikotinoylamido)-6-nitro-indolin-2-on. Prepared analogously to Example 1 from 1-ethyl-3,3-dimethyl-5-(2-dimethylamino-nicotinoylamido)-6-nitro-indolin-2-one.

Utbytte: 62% av det teoretiske,Yield: 62% of the theoretical,

smeltepunkt: fra 223°C (dekomp.)melting point: from 223°C (decomp.)

C20H25C12N50 x H20 (440,37) C20H25C12N50 x H20 (440.37)

Beregnet: C, 54,55; H, 6,18; N, 15,90Calculated: C, 54.55; H, 6.18; N, 15.90

Funnet: C, 54,79; H, 6,15; N, 15,78 Found: C, 54.79; H, 6.15; N, 15.78

Eksempel 56 Example 56

5-etyl-7,7-dimetyl-2-(2-morfolino-3-pyridyl)-6,7-dihydro-3H, 5H- pyrrolo[ 2, 3- f] benzimidazol- 6- on- hydroklorid x H20 5-ethyl-7,7-dimethyl-2-(2-morpholino-3-pyridyl)-6,7-dihydro-3H, 5H- pyrrolo[ 2, 3- f ] benzimidazole- 6- one- hydrochloride x H20

Fremstillet analogt med Eksempel 1 fra l-etyl-3,3-dimetyl-5-(2-morfolino-nikotinoylamido)-6-nitro-indolin-2-on. Utbytte: 28,2% av det teoretiske, Prepared analogously to Example 1 from 1-ethyl-3,3-dimethyl-5-(2-morpholino-nicotinoylamido)-6-nitro-indolin-2-one. Yield: 28.2% of the theoretical,

smeltepunkt: fra 185°C (dekomp.)melting point: from 185°C (decomp.)

C22H26C1N502x H20 (445,95) C22H26C1N502x H20 (445.95)

Beregnet: C, 59,25; H, 6,33; N, 15,70Calculated: C, 59.25; H, 6.33; N, 15.70

Funnet: C, 59,19; H, 6,06; N, 15,43 Found: C, 59.19; H, 6.06; N, 15.43

Eksempel 57 Example 57

5-etyl-7,7-dimetyl-2-(2,6-diklor-4-pyridyl)-6,7-dihydro-3H, 5H- pyrrolo [ 2 , 3- f ] benzimidazol- 6- on 5-ethyl-7,7-dimethyl-2-(2,6-dichloro-4-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one

Fremstillet analogt med Eksempel 1 fra l-etyl-5-(2,6-diklor-isonikotinoylamido)-3,3-dimetyl-6-nitro-indolin-2-on. Utbytte: 64,6% av det teoretiske, Prepared analogously to Example 1 from 1-ethyl-5-(2,6-dichloro-isonicotinoylamido)-3,3-dimethyl-6-nitro-indolin-2-one. Yield: 64.6% of the theoretical,

smeltepunkt: > 290°Cmelting point: > 290°C

C18H16C12N40 (375 , 27 ) C18H16C12N40 (375 , 27 )

Beregnet: C, 57,61; H, 4,30; N, 14,63Calculated: C, 57.61; H, 4.30; N, 14.63

Funnet: C, 57,42; H, 4,32; N, 14,38 Found: C, 57.42; H, 4.32; N, 14.38

Eksempel 58 Example 58

5-etyl-2-(2-klor-6-morfolino-4-pyridyl)-7,7-dimetyl-6,7-dihydro- 3H, 5H- pyrrolo[ 2, 3- f] benzimidazol- 6- on 5-ethyl-2-(2-chloro-6-morpholino-4-pyridyl)-7,7-dimethyl-6,7-dihydro- 3H, 5H- pyrrolo[ 2, 3- f ] benzimidazol- 6- one

Fremstillet analogt med Eksempel 1 fra l-etyl-5-(2-klor-6-morfolino-isonikotinoylamido)-3,3-dimetyl-6-nitro-indolin-2-on. Utbytte: 54,3% av det teoretiske, Prepared analogously to Example 1 from 1-ethyl-5-(2-chloro-6-morpholino-isonicotinoylamido)-3,3-dimethyl-6-nitro-indolin-2-one. Yield: 54.3% of the theoretical,

smeltepunkt: > 290°Cmelting point: > 290°C

C22<H>24C1N502(425 ,93) C22<H>24C1N502(425 .93)

Beregnet: C, 62,04; K, 5,68; N, 16,44Calculated: C, 62.04; K, 5.68; N, 16.44

Funnet: C, 61,91; H, 5,70; N, 16,23. Found: C, 61.91; H, 5.70; N, 16.23.

Eksempel 58 Example 58

5-etyl-2-(2-klor-6-morfolino-4-pyridyl)-7,7-dimetyl-6,7-dihydro- 3H, 5H- pyrrolo[ 2, 3- f] benzimidazol- 6- on 5-ethyl-2-(2-chloro-6-morpholino-4-pyridyl)-7,7-dimethyl-6,7-dihydro- 3H, 5H- pyrrolo[ 2, 3- f ] benzimidazol- 6- one

Fremstillet analogt med Eksempel 1 fra l-etyl-5-(2-klor-6-morfolino-isonikotinoylamido)-3,3-dimetyl-6-nitro-indolin-2-on. Utbytte: 54,3% av det teoretiske, Prepared analogously to Example 1 from 1-ethyl-5-(2-chloro-6-morpholino-isonicotinoylamido)-3,3-dimethyl-6-nitro-indolin-2-one. Yield: 54.3% of the theoretical,

smeltepunkt: >290°C.melting point: >290°C.

C22<H>24C1N502(425,93) C22<H>24C1N502(425.93)

Beregnet: C, 62,04; H, 5,68; N, 16,44Calculated: C, 62.04; H, 5.68; N, 16.44

Funnet: C, 61,91; H, 5,70; N, 16,23 Found: C, 61.91; H, 5.70; N, 16.23

Eksempel 59 Example 59

5-etyl-7,7-dimetyl-2-(5-pyrimidinyl)-6,7-dihydro-3H,5H-pyrrolo[ 2 , 3- f ] benzimidazol- 6- on 5-ethyl-7,7-dimethyl-2-(5-pyrimidinyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one

Fremstillet analogt med Eksempel 1 fra l-etyl-3,3-dimetyl-5-(pyrimidin-5-karbonamido)-6-nitro-indolin-2-on. Prepared analogously to Example 1 from 1-ethyl-3,3-dimethyl-5-(pyrimidine-5-carbonamido)-6-nitro-indolin-2-one.

Utbytte: 29,7% av det teoretiske,Yield: 29.7% of the theoretical,

smeltepunkt: > 300°Cmelting point: > 300°C

C17H17N50 (307,36) C17H17N50 (307.36)

Beregnet: C, 66,43; H, 5,58; N, 22,79Calculated: C, 66.43; H, 5.58; N, 22.79

Funnet: C, 66,26; H, 5,54; N, 22,67 Found: C, 66.26; H, 5.54; N, 22.67

Eksempel 60 Example 60

7,7-dimetyl-5-n-propyl-2-(2-tienyl)-6,7-dihydro-3H,5H-pyrrolo[ 2, 3- f] benzimidazol- 6- on 7,7-Dimethyl-5-n-propyl-2-(2-thienyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one

Fremstillet analogt med Eksempel 1 fra 3,3-dimetyl-l-n-propyl-6-nitro-5-(2-tenoylamido)-indolin-2-on. Prepared analogously to Example 1 from 3,3-dimethyl-1-n-propyl-6-nitro-5-(2-thenoylamido)-indolin-2-one.

Utbytte: 55,5% av det teoretiske,Yield: 55.5% of the theoretical,

smeltepunkt: > 280°C (etylacetat/isopropanol)melting point: > 280°C (ethyl acetate/isopropanol)

C18<H>19N3OS ( 325 ,43 ) C18<H>19N3OS ( 325 .43 )

Beregnet: C, 66,43; H, 5,88; N, 12,91Calculated: C, 66.43; H, 5.88; N, 12.91

Funnet: C, 66,32; H, 5,96; N, 12,80 Found: C, 66.32; H, 5.96; N, 12.80

Eksempel 61 Example 61

7,7-dimetyl-2-(2-furyl)-5-n-propyl-6,7-dihydro-3H,5H-pyrrolo-[ 2 , 3- f ] benzimidazol- 6- on 7,7-dimethyl-2-(2-furyl)-5-n-propyl-6,7-dihydro-3H,5H-pyrrolo-[2,3-f]benzimidazol-6-one

Fremstillet analogt med Eksempel 1 fra 3,3-dimetyl-5-(2-furoylamido)-6-nitro-1-n-propyl-indolin-2-on. Prepared analogously to Example 1 from 3,3-dimethyl-5-(2-furoylamido)-6-nitro-1-n-propyl-indolin-2-one.

Utbytte: 58% av det teoretiske,Yield: 58% of the theoretical,

smeltepunkt: > 290°C (etylacetat/isopropanol)melting point: > 290°C (ethyl acetate/isopropanol)

C18<H>19N302(309, 37 ) C18<H>19N302(309, 37 )

Beregnet: C, 69,88; H, 6,19; N, 13,58Calcd: C, 69.88; H, 6.19; N, 13.58

Funnet: c, 69,62; H, 6,21; N, 13,57 Found: c, 69.62; H, 6.21; N, 13.57

Eksempel 62 Example 62

7,7-dimetyl-2-(4-metylmerkaptofenyl)-5-n-propyl-6,7-dihydro-3H, 5H- pyrrolo[ 2, 3- f] benzimidazol- 6- on 7,7-dimethyl-2-(4-methylmercaptophenyl)-5-n-propyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one

Fremstillet analogt med Eksempel 1 fra 3,3-dimetyl-5-(4-metylmerkapto-benzoylamido)-6-nitro-1-n-propyl-indolin-2-on. Utbytte: 29,3% av det teoretiske, Prepared analogously to Example 1 from 3,3-dimethyl-5-(4-methylmercapto-benzoylamido)-6-nitro-1-n-propyl-indolin-2-one. Yield: 29.3% of the theoretical,

smeltepunkt: 286°Cmelting point: 286°C

C21H23N3OS (365,49) C21H23N3OS (365.49)

Beregnet: C, 69,01; H, 6,34; N, 11,50Calculated: C, 69.01; H, 6.34; N, 11.50

Funnet: C, 68,87; H, 6,42; N, 11,36 Found: C, 68.87; H, 6.42; N, 11.36

Eksempel 63 Example 63

7,7-dimetyl-5-n-pentyl-2-(2-tienyl)-6,7-dihydro-3H,5H-pyrrolo[ 2 , 3- f ] benzimidazol- 6- on 7,7-dimethyl-5-n-pentyl-2-(2-thienyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one

Fremstillet analogt med Eksempel 1 fra 3,3-dimetyl-6-nitro-l-n-pentyl-5-(2-tenoylamido)-indolin-2-on. Prepared analogously to Example 1 from 3,3-dimethyl-6-nitro-1-n-pentyl-5-(2-thenoylamido)-indolin-2-one.

Utbytte: 70,3% av det teoretiske,Yield: 70.3% of the theoretical,

smeltepunkt: 216°Cmelting point: 216°C

C20<H>23N3OS (353,49) C20<H>23N3OS (353.49)

Beregnet: C, 67,96; H, 6,56; N, 11,89Calcd: C, 67.96; H, 6.56; N, 11.89

Funnet: C, 67,77; H, 6,61; N, 11,89 Found: C, 67.77; H, 6.61; N, 11.89

Eksempel 64 Example 64

5- etyl-2-(4-cyan-fenyl)-7,7-dimetyl-6,7-dihydro-3H,5H-pyrrolo-[ 2, 3- f] benzimidazol- 6- on x 0, 5 H2 0 4 g (10,5 mmol) l-etyl-5-(4-cyan-benzoylamido)-3,3-dimetyl-6- nitro-indolin-2-on ble oppløst i 100 ml iseddik, tilsatt 0,5 g -10% palladium/kull og hydrert i 1 time ved romtemperatur under 5 bar hydrogentrykk. Etter frafiltrering av katalysatoren ble filtratet hvor nå l-etyl-6-amino-5-(4-cyan-benzoyl-amino)-3,3-dimetyl-indolin-2-on foreligger, oppvarmet på dampbad i 3 timer for å oppnå cyklisering. Etter avdestillering av opp-løsningsmidlet ble residuet tatt opp i etylenklorid/etanol = 5:1, vasket med fortynnet ammoniakk og deretter med vann og tørket, hvorpå oppløsningsmidlet ble avdestillert. 5- ethyl-2-(4-cyano-phenyl)-7,7-dimethyl-6,7-dihydro-3H,5H-pyrrolo-[2,3-f]benzimidazol-6-one x 0.5 H2 0 4 g (10.5 mmol) of 1-ethyl-5-(4-cyano-benzoylamido)-3,3-dimethyl-6-nitro-indolin-2-one was dissolved in 100 ml of glacial acetic acid, added 0.5 g - 10% palladium/charcoal and hydrated for 1 hour at room temperature under 5 bar hydrogen pressure. After filtering off the catalyst, the filtrate, which now contains 1-ethyl-6-amino-5-(4-cyano-benzoyl-amino)-3,3-dimethyl-indolin-2-one, was heated on a steam bath for 3 hours to obtain cyclization. After distilling off the solvent, the residue was taken up in ethylene chloride/ethanol = 5:1, washed with dilute ammonia and then with water and dried, after which the solvent was distilled off.

Utbytte: 1,15 g (33,9% av det teoretiske),Yield: 1.15 g (33.9% of the theoretical),

smeltepunkt: >295°Cmelting point: >295°C

C20H18N40 x 0,5 H20 (339,40) C20H18N40 x 0.5 H20 (339.40)

Beregnet: C, 70,78; H, 5,64; N, 16,51Calculated: C, 70.78; H, 5.64; N, 16.51

Funnet: C, 70,58; H, 5,60; N, 16,38 Found: C, 70.58; H, 5.60; N, 16.38

Eksempel 65 Example 65

5-etyl-2-(2-klorfenyl)-7,7-dimetyl-6,7-dihydro-3H,5H-pyrrolo-[ 2 , 3- f ] benzimidazol- 6- on- hydroklorid 5-ethyl-2-(2-chlorophenyl)-7,7-dimethyl-6,7-dihydro-3H,5H-pyrrolo-[2,3-f]benzimidazol-6-one hydrochloride

a) En oppløsning av 5,8 g (15 mmol) l-etyl-5-(2-klor-benzoyl-amido)-3,3-dimetyl-6-nitro-indolin-2-on i 60 ml iseddik ble a) A solution of 5.8 g (15 mmol) of 1-ethyl-5-(2-chloro-benzoyl-amido)-3,3-dimethyl-6-nitro-indolin-2-one in 60 ml of glacial acetic acid was

tilsatt 0,6 g Raney-nikkel og hydrert ved 80°C under 5 bar hydrogentrykk i 4 timer. Etter frafiltrering av katalysatoren added 0.6 g Raney nickel and hydrogenated at 80°C under 5 bar hydrogen pressure for 4 hours. After filtering off the catalyst

ble oppløsningsmidlet avdestillert, hvorpå residuet ble oppløst i vann og gjort alkalisk med ammoniakk. Bunnfallet ble suget av og vasket med vann, etylacetat og tilslutt med eter, hvorved 1-etyl-6-amino-5-(2-klorbenzoylamido)-3,3-dimetyl-indol-2-on ble oppnådd. the solvent was distilled off, whereupon the residue was dissolved in water and made alkaline with ammonia. The precipitate was sucked off and washed with water, ethyl acetate and finally with ether, whereby 1-ethyl-6-amino-5-(2-chlorobenzoylamido)-3,3-dimethyl-indol-2-one was obtained.

Utbytte: 1,6 g (30% av det teoretiske),Yield: 1.6 g (30% of the theoretical),

smeltepunkt: 169°Cmelting point: 169°C

C19<H>20C1N302(357 ,85 ) C19<H>20C1N302(357 .85 )

Beregnet: C, 63,77; H, 5,63; N, 11,74; Cl, 9,91 Calculated: C, 63.77; H, 5.63; N, 11.74; Cl, 9.91

Funnet: C, 63,79; H, 5,62; N, 11,67; Cl, 9,72 b) Den under a) oppnådde forbindelse ble oppløst i 50 ml etanol og 50 ml konsentrert saltsyre og kokt under tilbakeløps-kjøling i 2 dager. Etter avkjøling ble krystallene frafiltrert og vasket med vann og aceton og tilslutt med eter. Found: C, 63.79; H, 5.62; N, 11.67; Cl, 9.72 b) The compound obtained under a) was dissolved in 50 ml of ethanol and 50 ml of concentrated hydrochloric acid and boiled under reflux for 2 days. After cooling, the crystals were filtered off and washed with water and acetone and finally with ether.

Utbytte: 1,3 g (73,5% av det teoretiske),Yield: 1.3 g (73.5% of the theoretical),

smeltepunkt: 305°C (dekomp.)melting point: 305°C (decomp.)

C19H19C12N30 (376,29) C19H19C12N30 (376.29)

Beregnet: C, 60,65; H, 5,09; N, 11,17; Cl, 18,84 Calculated: C, 60.65; H, 5.09; N, 11.17; Cl, 18.84

Funnet: C, 60,77; H, 4,95; N, 11,09; Cl, 18,72 Found: C, 60.77; H, 4.95; N, 11.09; Cl, 18.72

Eksempel 66 Example 66

2-(2-fenylvinyl)-5,7,7-trimetyl-6,7-dihydro-3H,5H-pyrrolo-[ 2, 3- f] benzimidazol- 6- on 2-(2-phenylvinyl)-5,7,7-trimethyl-6,7-dihydro-3H,5H-pyrrolo-[2,3-f]benzimidazol-6-one

Fremstillet analogt med Eksempel 65 fra 5-(2-fenylakryl-amido)-6-nitro-1,3,3-trimetyl-indolin-2-on. Prepared analogously to Example 65 from 5-(2-phenylacrylamido)-6-nitro-1,3,3-trimethyl-indolin-2-one.

Utbytte: 73% av det teoretiske,Yield: 73% of the theoretical,

smeltepunkt: 243-244°C (etylacetat)melting point: 243-244°C (ethyl acetate)

C20<H>19N30 ( 317 , 39) C20<H>19N30 ( 317 , 39)

Beregnet: C, 75,69; H, 6,03; N, 13,24Calcd: C, 75.69; H, 6.03; N, 13,24

Funnet: C, 75,47; H, 6,25; N, 12,96 Found: C, 75.47; H, 6.25; N, 12.96

Eksempel 67 Example 67

2-(2-pyrazinyl)-5,7,7-trimetyl-6,7-dihydro-3H,5H-pyrrolo-[ 2 , 3- f ] benzimidazol- 6- on 2-(2-pyrazinyl)-5,7,7-trimethyl-6,7-dihydro-3H,5H-pyrrolo-[2,3-f]benzimidazol-6-one

Fremstillet analogt med Eksempel 65 fra 6-nitro-5-(2-pyrazinoylamido)-1,3,3-trimetyl-indolin-2-on. Prepared analogously to Example 65 from 6-nitro-5-(2-pyrazinoylamido)-1,3,3-trimethyl-indolin-2-one.

Utbytte: 61,6% av det teoretiske,Yield: 61.6% of the theoretical,

smeltepunkt: > 280°Cmelting point: > 280°C

C16<H>15N50 (293 ,33 ) C16<H>15N50 (293 .33 )

Beregnet: C, 65,52; H, 5,15; N, 23,88Calculated: C, 65.52; H, 5.15; N, 23.88

Funnet: C, 65,34; H, 5,18; N, 23,61 Found: C, 65.34; H, 5.18; N, 23.61

Eksempel 68 Example 68

2-(2-tienyl)-5,7,7-trimetyl-6,7-dihydro-3H,5H-pyrrolo-[ 2, 3- f] benzimidazol- 6- on x 0, 5 H20 2-(2-thienyl)-5,7,7-trimethyl-6,7-dihydro-3H,5H-pyrrolo-[2,3-f]benzimidazol-6-one x 0.5 H2O

Fremstillet analogt med Eksempel 65 fra 6-nitro-5-(2-tenoylamido)-1,3,3-trimetyl-indolin-2-on. Prepared analogously to Example 65 from 6-nitro-5-(2-thenoylamido)-1,3,3-trimethyl-indolin-2-one.

Utbytte: 37,8% av det teoretiske,Yield: 37.8% of the theoretical,

smeltepunkt: fra 130°Cmelting point: from 130°C

C16H15N3OS x 0,5 H20 (306,38) C16H15N3OS x 0.5 H2O (306.38)

Beregnet: C, 62,72; H, 5,26; N, 13,72Calculated: C, 62.72; H, 5.26; N, 13.72

Funnet: C, 62,93; H, 5,26; N, 13,62 Found: C, 62.93; H, 5.26; N, 13.62

Eksempel 69 Example 69

7,7-dimetyl-5-n-propyl-2-(2-pyrazinyl)-6,7-dihydro-3H,5H-pyrrolo[ 2, 3- f] benzimidazol- 6- on x 0, 3 H20 7,7-Dimethyl-5-n-propyl-2-(2-pyrazinyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one x 0.3H20

Fremstillet analogt med Eksempel 65 fra 3,3-dimetyl-6-nitro-1-n-propyl-5-(2-pyrazinoylamido)-indolin-2-on. Prepared analogously to Example 65 from 3,3-dimethyl-6-nitro-1-n-propyl-5-(2-pyrazinoylamido)-indolin-2-one.

Utbytte: 54,7% av det teoretiske,Yield: 54.7% of the theoretical,

smeltepunkt: 268°Cmelting point: 268°C

C18H19N50 x 0,3 H20 (326,79) C18H19N50 x 0.3 H2O (326.79)

Beregnet: C, 66,16; H, 6,05; N, 21,43Calculated: C, 66.16; H, 6.05; N, 21.43

Funnet: C, 66,29; H, 5,93; N, 21,25 Found: C, 66.29; H, 5.93; N, 21.25

Eksempel 70 Example 70

5-etyl-7,7-dimetyl-2-(4-metyl-oksazol-5-yl)-6,7-dihydro-3H, 5H- pyrrolo[ 2, 3- f] benzimidazol- 6- on 5-ethyl-7,7-dimethyl-2-(4-methyl-oxazol-5-yl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one

En oppløsning av 2,6 g (7,25 mmol) l-etyl-3,3-dimetyl-5-(4-metyl-5-oksazolyl-karbonamido)-6-nitro-indolin-2-on i 50 ml iseddik ble tilsatt 0,3 g 5% platina/kull og hydrert. Etter avsluttet hydrogenopptak ble katalysatoren frafiltrert og filtratet kokt under tilbakeløpskjøling i 3 timer, hvorpå oppløsningsmidlet ble avdestillert, residuet tilsatt vann, gjort alkalisk med ammoniakk og ekstrahert med etylenklorid. Ekstraktet ble tørket, oppløsningsmidlet avdestillert og residuet omkrystallisert fra etylacetat. A solution of 2.6 g (7.25 mmol) of 1-ethyl-3,3-dimethyl-5-(4-methyl-5-oxazolyl-carbonamido)-6-nitro-indolin-2-one in 50 ml of glacial acetic acid was added 0.3 g of 5% platinum/charcoal and hydrated. After completion of hydrogen uptake, the catalyst was filtered off and the filtrate boiled under reflux for 3 hours, after which the solvent was distilled off, the residue added to water, made alkaline with ammonia and extracted with ethylene chloride. The extract was dried, the solvent distilled off and the residue recrystallized from ethyl acetate.

Utbytte: 1 g (44,4% av det teoretiske),Yield: 1 g (44.4% of the theoretical),

smeltepunkt: 244°Cmelting point: 244°C

C17H18N402(310, 36) C17H18N402(310, 36)

Beregnet: C, 65,79; H, 5,85; N, 18,05Calcd: C, 65.79; H, 5.85; N, 18.05

Funnet: C, 65,60; H, 5,98; N, 17,98 Found: C, 65.60; H, 5.98; N, 17.98

Eksempel 71 Example 71

5-etyl-2-(4-amino-3,5-diklorfenyl)-7,7-dimetyl-6,7-dihydro-3H, 5H- pyrrolo[ 2, 3- f] ben2imidazol- 6- on 5-ethyl-2-(4-amino-3,5-dichlorophenyl)-7,7-dimethyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]ben2imidazol-6-one

Fremstillet analogt med Eksempel 70 fra l-etyl-5-(4-amino-3,5-diklor-benzoylamido)-3,3-dimety1-6-nitro-indolin-2-on. Utbytte: 53% av det teoretiske, Prepared analogously to Example 70 from 1-ethyl-5-(4-amino-3,5-dichloro-benzoylamido)-3,3-dimethyl-6-nitro-indolin-2-one. Yield: 53% of the theoretical,

smeltepunkt: > 300 °C (etylacetat/eter)melting point: > 300 °C (ethyl acetate/ether)

C19H18C12N40 (389,30) C19H18C12N40 (389.30)

Beregnet: C, 58,62; H, 4,66; N, 14,39Calculated: C, 58.62; H, 4.66; N, 14.39

Funnet: C, 58,49; H, 4,76; N, 14,60 Found: C, 58.49; H, 4.76; N, 14.60

Eksempel 72 Example 72

5- etyl-7,7-dimetyl-2-(4-pyrimidinyl)-6,7-dihydro-3H,5H-pyrrolo[ 2, 3- f] benzimidazol- 6- on- hydroklorid 5- ethyl-7,7-dimethyl-2-(4-pyrimidinyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one hydrochloride

Fremstilet analogt med Eksempel 70 fra l-etyl-3,3-dimetyl-6- nitro-5-(pyrimidin-4-karbonamido)-indolin-2-on. Prepared analogously to Example 70 from 1-ethyl-3,3-dimethyl-6-nitro-5-(pyrimidine-4-carbonamido)-indolin-2-one.

Utbytte: 11% av det teoretiske,Yield: 11% of the theoretical,

smeltepunkt: 198°C (dekomp.)melting point: 198°C (decomp.)

C17H18C1N50 (343,82) C17H18C1N50 (343.82)

Beregnet: C, 59,39; H, 5,28; N, 20,37Calculated: C, 59.39; H, 5.28; N, 20.37

Funnet: C, 59,59; H, 5,45; N, 20,54 Found: C, 59.59; H, 5.45; N, 20.54

Eksempel 73 Example 73

5-etyl-7,7-dimetyl-2-(4-pyridyl)-6,7-dihydro-3H,5H-pyrrolo-[ 2 , 3- f ] benzimidazol- 6- on 3 g (0,01 mol) l-etyl-5,6-diamino-3,3-dimetyl-indolin-2-on-dihydroklorid ble blandet med 2,67 g (0,015 mmol) isonikotinsyreklorid-hydroklorid i 100 ml metylenklorid og ved romtemperatur dråpevis tilsatt 5 g trietylamin og omrørt i 1 time. Etter avdestillering av oppløsningsmidlet ble residuet tilsatt 50 ml etanol, 25 ml kons. saltsyre og 10 ml vann og kokt under tilbakeløpskjøling i 18 timer. Etter avdestillering av opp-løsningsmidlet ble residuet tatt opp i etanol, gjort alkalisk med ammoniakk og langsomt tilsatt vann. Bunnfallet ble suget av og omkrystallisert fra isopropanol/diisopropyleter. 5-ethyl-7,7-dimethyl-2-(4-pyridyl)-6,7-dihydro-3H,5H-pyrrolo-[2,3-f]benzimidazol-6-one 3 g (0.01 mol) 1-ethyl-5,6-diamino-3,3-dimethyl-indolin-2-one dihydrochloride was mixed with 2.67 g (0.015 mmol) of isonicotinic acid chloride hydrochloride in 100 ml of methylene chloride and at room temperature 5 g of triethylamine and stirred for 1 hour. After distilling off the solvent, the residue was added to 50 ml of ethanol, 25 ml of conc. hydrochloric acid and 10 ml of water and boiled under reflux for 18 hours. After distilling off the solvent, the residue was taken up in ethanol, made alkaline with ammonia and water slowly added. The precipitate was suctioned off and recrystallized from isopropanol/diisopropyl ether.

Utbytte: 1,3 g (42,5% av det teoretiske),Yield: 1.3 g (42.5% of the theoretical),

smeltepunkt: 296-298°Cmelting point: 296-298°C

C18<H>18N40 (306,37) C18<H>18N40 (306.37)

Beregnet: C, 70,57; H, 5,92; N, 18,29Calculated: C, 70.57; H, 5.92; N, 18,29

Funnet: C, 70,41; H, 6,00; N, 18,06 Found: C, 70.41; H, 6.00; N, 18.06

Eksempel 74 Example 74

5-etyl-7,7-dimetyl-2-(4-nitrofenyl)-6,7-dihydro-3H,5H-pyrrolo[ 2, 3- f] benzimidazol- 6- on 5-ethyl-7,7-dimethyl-2-(4-nitrophenyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one

Fremstillet analogt med Eksempel 73 fra 4-nitro-benzoyl-klorid og l-etyl-5,6-diamino-3,3-dimetyl-indolin-2-on. Utbytte: 23% av det teoretiske, Prepared analogously to Example 73 from 4-nitro-benzoyl chloride and 1-ethyl-5,6-diamino-3,3-dimethyl-indolin-2-one. Yield: 23% of the theoretical,

smeltepunkt: > 290°Cmelting point: > 290°C

C19<H>18<N>403(350,38) C19<H>18<N>403(350.38)

Beregnet: C, 65,13; H, 5,18; N, 15,99Calculated: C, 65.13; H, 5.18; N, 15.99

Funnet: C, 65,35; H, 5,15; N, 16,16 Found: C, 65.35; H, 5.15; N, 16,16

Eksempel 75 Example 75

2-(4-pyridyl)-1,5,7,7-tetrametyl-6,7-dihydro-lH,5H-pyrrolo-[ 2, 3- f] benzimidazol- 6- on 2-(4-pyridyl)-1,5,7,7-tetramethyl-6,7-dihydro-1H,5H-pyrrolo-[2,3-f]benzimidazol-6-one

Fremstillet analogt med Eksempel 1 fra 6-nitro-5-(N-metyl-isonikotinoylamido )-1,3,3-trimetyl-indolin-2-on. Prepared analogously to Example 1 from 6-nitro-5-(N-methyl-isonicotinoylamido)-1,3,3-trimethyl-indolin-2-one.

Utbytte: 42% av det teoretiske,Yield: 42% of the theoretical,

smeltepunkt: 250-252°C (etylacetat)melting point: 250-252°C (ethyl acetate)

C18<H>18N40 (306,37) C18<H>18N40 (306.37)

Beregnet: C, 70,57; H, 5,92; N, 18,29Calculated: C, 70.57; H, 5.92; N, 18,29

Funnet: C, 70,54; H, 6,05; N, 18,26 Found: C, 70.54; H, 6.05; N, 18,26

Eksempel 76 Example 76

7,7-dimetyl-5-n-pentyl-2-(2-pyrazinyl)-6,7-dihydro-3H,5H-pyrrolo [ 2 , 3- f ] benzimidazol- 6- on 7,7-dimethyl-5-n-pentyl-2-(2-pyrazinyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one

Fremstillet analogt med Eksempel 65 fra 3,3-dimetyl-6-nitro-l-n-pentyl-5-(2-pyrazinoylamido)-indolin-2-on. Utbytte: 48,8% av det teoretiske, Prepared analogously to Example 65 from 3,3-dimethyl-6-nitro-1-n-pentyl-5-(2-pyrazinoylamido)-indolin-2-one. Yield: 48.8% of the theoretical,

smeltepunkt: 215-217°Cmelting point: 215-217°C

C20<H>23N50 (349,43) C20<H>23N50 (349.43)

Beregnet: C, 68,75; H, 6,63; N, 20,04Calcd: C, 68.75; H, 6.63; N, 20.04

Funnet: C, 68,55; H, 6,68; N, 20,05 Found: C, 68.55; H, 6.68; N, 20.05

Eksempel 77 Example 77

7,7-dimetyl-2-(2-furyl)-5-n-pentyl-6,7-dihydro-3H,5H-pyrrolo[ 2/ 3- f] benzimidazol- 6- on 7,7-dimethyl-2-(2-furyl)-5-n-pentyl-6,7-dihydro-3H,5H-pyrrolo[ 2/ 3- f ] benzimidazol- 6- one

Fremstillet analogt med Eksempel 1 fra 3,3-dimetyl-5-(2-furoylamido)-6-nitro-l-n-pentyl-indolin-2-on. Prepared analogously to Example 1 from 3,3-dimethyl-5-(2-furoylamido)-6-nitro-1-n-pentyl-indolin-2-one.

Utbytte: 87% av det teoretiske,Yield: 87% of the theoretical,

smeltepunkt: 152-154°C (etylacetat/diisopropyleter)melting point: 152-154°C (ethyl acetate/diisopropyl ether)

C20<H>23<N>302(337 ,42) C20<H>23<N>302(337 .42)

Beregnet: C, 71,19; H, 6,87; N, 12,45Calculated: C, 71.19; H, 6.87; N, 12.45

Funnet: C, 70,92; H, 7,02; N, 12,38 Found: C, 70.92; H, 7.02; N, 12.38

Eksempel 78 Example 78

5-etyl-7,7-dimetyl-2-[2-(4-pyridyl)-etyl]-6,7-dihydro-3H,5H-pyrrolo[ 2, 3- f ] benzimidazol- 6- on 5-ethyl-7,7-dimethyl-2-[2-(4-pyridyl)-ethyl]-6,7-dihydro-3H,5H-pyrrolo[ 2, 3- f ] benzimidazol-6-one

2,92 g (0,01 mol) l-etyl-5,6-diamino-3,3-dimetyl-indolin-2-on-dihydroklorid og 2 g (0,013 mol) 3-(4-pyridyl)-propionsyre ble blandet godt, tilsatt 30 g fosforoksyklorid og omrørt i 1 time ved 100°C. Overskuddet av fosforoksyklorid ble deretter avdestillert, hvorpå residuet ble tilsatt isvann, gjort alkalisk med ammoniakk og ekstrahert 3 ganger med en blanding av kloroform og etanol (4:1). Ekstraktet ble vasket med vann, tørket med natriumsulfat, hvoretter oppløsningsmidlet ble avdestillert. For søylekromatografisk rensing ble residuet tatt opp i etylenklorid/etanol = 9:1, tilsatt til en kiselgelsøyle (partikkelstørrelse 40-63 p) og eluert med den samme oppløsnings-middelblanding.Ensartede fraksjoner ble slått sammen, opp-løsningsmidlet avdestillert og residuet omkrystallisert fra etylacetat/diisopropyleter. 2.92 g (0.01 mol) of 1-ethyl-5,6-diamino-3,3-dimethyl-indolin-2-one dihydrochloride and 2 g (0.013 mol) of 3-(4-pyridyl)-propionic acid were mixed well, added 30 g of phosphorus oxychloride and stirred for 1 hour at 100°C. The excess of phosphorus oxychloride was then distilled off, whereupon the residue was added to ice water, made alkaline with ammonia and extracted 3 times with a mixture of chloroform and ethanol (4:1). The extract was washed with water, dried with sodium sulfate, after which the solvent was distilled off. For column chromatographic purification, the residue was taken up in ethylene chloride/ethanol = 9:1, added to a silica gel column (particle size 40-63 p) and eluted with the same solvent mixture. Uniform fractions were combined, the solvent distilled off and the residue recrystallized from ethyl acetate/diisopropyl ether.

Utbytte: 1,68 g (50% av det teoretiske),Yield: 1.68 g (50% of the theoretical),

smeltepunkt: 139-141°Cmelting point: 139-141°C

C20<H>22N40 (334,43) C20<H>22N40 (334.43)

Beregnet: C, 71,83; H, 6,63; N, 16,75Calculated: C, 71.83; H, 6.63; N, 16.75

Funnet: C, 71,59; H, 6,82; N, 16,49 Found: C, 71.59; H, 6.82; N, 16.49

Eksempel 79 Example 79

5-etyl-7,7-dimetyl-2-(3-pikolyl)-6,7-dihydro-3H,5H-pyrrolo-[ 2, 3- f] benzimidazol- 6- on 5-ethyl-7,7-dimethyl-2-(3-picolyl)-6,7-dihydro-3H,5H-pyrrolo-[2,3-f]benzimidazol-6-one

Fremstillet analogt med Eksempel 78 fra 3-pyridyl-eddiksyre og l-etyl-5,6-diamino-3,3-dimetyl-indolin-2-on. Prepared analogously to Example 78 from 3-pyridyl-acetic acid and 1-ethyl-5,6-diamino-3,3-dimethyl-indolin-2-one.

Utbytte: 16,3% av det teoretiske,Yield: 16.3% of the theoretical,

smeltepunkt: 194°C (etylacetat)melting point: 194°C (ethyl acetate)

Cig<H>20N40 (320,40) Cig<H>20N40 (320.40)

Beregnet: C, 71,23; H, 6,29; N, 17,49Calculated: C, 71.23; H, 6.29; N, 17.49

Funnet: C, 71,23; H, 6,38; N, 17,61 Found: C, 71.23; H, 6.38; N, 17.61

Eksempel 80 Example 80

5-etyl-7,7-dimetyl-2-[2-(4-pyridyl)-vinyl]-6,7-dihydro-3H,5H-pyrrolo[ 2 , 3- f ] benzimidazol- 6- on 5-ethyl-7,7-dimethyl-2-[2-(4-pyridyl)-vinyl]-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one

Fremstillet analogt med Eksempel 78 fra 3-(4-pyridyl)-akrylsyre og l-etyl-5,6-diamino-3,3-dimetyl-indolin-2-on. Utbytte: 23% av det teoretiske, Prepared analogously to Example 78 from 3-(4-pyridyl)-acrylic acid and 1-ethyl-5,6-diamino-3,3-dimethyl-indolin-2-one. Yield: 23% of the theoretical,

smeltepunkt: 262-263°C (etylacetat/diisopropyleter)melting point: 262-263°C (ethyl acetate/diisopropyl ether)

<C>20H20N40 (332,41) <C>20H20N40 (332.41)

Beregnet: C, 72,27; H, 6,06; N, 16,86Calculated: C, 72.27; H, 6.06; N, 16.86

Funnet: C, 72,05; H, 6,13; N, 16,69 Found: C, 72.05; H, 6.13; N, 16.69

Eksempel 81 Example 81

5-etyl-2-(4-klor-7-trifluormetyl-3-kinoyl)-7,7-dimetyl-6,7-dihydro- 3H, 5H- pyrrolo[ 2, 3- f] benzimidazol- 6- on x 0, 5 H20 5-ethyl-2-(4-chloro-7-trifluoromethyl-3-quinoyl)-7,7-dimethyl-6,7-dihydro- 3H, 5H- pyrrolo[ 2, 3- f ] benzimidazol- 6- one x 0.5 H 2 O

Fremstillet analogt med Eksempel 78 fra 4-hydroksy-7-trifluormetyl-kinolin-3-karbonsyre og l-etyl-5,6-diamino-3,3-dimetyl-indolin-2-on. Prepared analogously to Example 78 from 4-hydroxy-7-trifluoromethyl-quinoline-3-carboxylic acid and 1-ethyl-5,6-diamino-3,3-dimethyl-indolin-2-one.

Utbytte: 18% av det teoretiske,Yield: 18% of the theoretical,

smeltepunkt: 198-199°C (etylacetat)melting point: 198-199°C (ethyl acetate)

C23H18C1F3N40 x 0,5 H20 (467,88) C23H18C1F3N40 x 0.5 H2O (467.88)

Beregnet: C, 59,04; H, 4,09; N, 11,98Calculated: C, 59.04; H, 4.09; N, 11.98

Funnet: C, 59,29; H, 4,15; N, 12,20 Found: C, 59.29; H, 4.15; N, 12.20

Eksempel 82 5-etyl-7,7-dimetyl-2-(4-pyridazinyl)-6,7-dihydro-3H,5H-pyrrolo[ 2, 3- f] benzimidazol- 6- on x 0, 5 H20 Example 82 5-ethyl-7,7-dimethyl-2-(4-pyridazinyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one x 0.5 H 2 O

Fremstillet analogt med Eksempel 78 fra pyridazin-4-karbonsyre og l-etyl-5,6-diamino-3,3-dimetyl-indolin-2-on. Utbytte: 15% av det teoretiske, Prepared analogously to Example 78 from pyridazine-4-carboxylic acid and 1-ethyl-5,6-diamino-3,3-dimethyl-indolin-2-one. Yield: 15% of the theoretical,

smeltepunkt: > 290°Cmelting point: > 290°C

C17H17N50 x 0,5 H20 (316,36) C17H17N50 x 0.5 H2O (316.36)

Beregnet: C, 64,54; H, 5,73; N, 22,14Calculated: C, 64.54; H, 5.73; N, 22.14

Funnet: C, 64,75; K, 5,81; N, 21,93 Found: C, 64.75; K, 5.81; N, 21.93

Eksempel 83 Example 83

5-etyl-7,7-dimetyl-2-(6-metyl-3-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[ 2, 3- f] benzimidazol- 6- on 5-ethyl-7,7-dimethyl-2-(6-methyl-3-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one

Fremstillet analogt med Eksempel 78 fra 6-metyl-nikotinsyre og l-etyl-5,6-diamino-3,3-dimetyl-indolin-2-on. Prepared analogously to Example 78 from 6-methyl-nicotinic acid and 1-ethyl-5,6-diamino-3,3-dimethyl-indolin-2-one.

Utbytte: 26,3% av det teoretiske,Yield: 26.3% of the theoretical,

smeltepunkt: 267°Cmelting point: 267°C

C19<H>20N40 (320,40) C19<H>20N40 (320.40)

Beregnet: C, 71,23; H, 6,29; N, 17,49Calculated: C, 71.23; H, 6.29; N, 17.49

Funnet: C, 70,98; H, 6,29; N, 17,23 Found: C, 70.98; H, 6.29; N, 17.23

Eksempel 84 Example 84

2-(2-klor-6-metoksy-4-kinolyl)-5-etyl-7,7-dimetyl-6,7-dihydro-3H, 5H- pyrrolo[ 2 , 3- f ] benzimidazol- 6- on 2-(2-chloro-6-methoxy-4-quinolyl)-5-ethyl-7,7-dimethyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one

Fremstillet analogt med Eksempel 78 fra 2-hydroksy-6-metoksy-kinolin-4-karbonsyre og l-etyl-5,6-diamino-3,3-dimetyl-indolin-2-on. Prepared analogously to Example 78 from 2-hydroxy-6-methoxy-quinoline-4-carboxylic acid and 1-ethyl-5,6-diamino-3,3-dimethyl-indolin-2-one.

Utbytte: 30% av det teoretiske,Yield: 30% of the theoretical,

smeltepunkt: fra 198°C (dioksan)melting point: from 198°C (dioxane)

C23<H>21C1N402(420,91) C23<H>21C1N402(420.91)

Beregnet: C, 65,63; H, 5,03; N, 13,31Calculated: C, 65.63; H, 5.03; N, 13.31

Funnet: C, 65,40; H, 4,96; N, 13,36 Found: C, 65.40; H, 4.96; N, 13.36

Eksempel 85 Example 85

5-etyl-7,7-dimetyl-2-(2-fenyl-4-kinolyl)-6,7-dihydro-3H,5H-pyrrolo[ 2, 3- f] benzimidazol- 6- on x 0, 5 H20 5-ethyl-7,7-dimethyl-2-(2-phenyl-4-quinolyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one x 0.5 H20

Fremstillet analogt med Eksempel 78 fra 2-fenyl-kinolin-4-karbonsyre og l-etyl-5,6-diamino-3,3-dimetyl-indolin-2-on. Utbytte: 25,5% av det teoretiske, Prepared analogously to Example 78 from 2-phenyl-quinoline-4-carboxylic acid and 1-ethyl-5,6-diamino-3,3-dimethyl-indolin-2-one. Yield: 25.5% of the theoretical,

smeltepunkt: fra 165°C (toluen)melting point: from 165°C (toluene)

C28H24N40 x 0,5 H20 (441,53) C28H24N40 x 0.5 H2O (441.53)

Beregnet: C, 76,17; K, 5,71; N, 12,69Calculated: C, 76.17; K, 5.71; N, 12.69

Funnet: C, 75,95; H, 5,92; N, 12,45 Found: C, 75.95; H, 5.92; N, 12.45

Eksempel 86 Example 86

5-etyl-7,7-dimetyl-2-(4-pyridyl)-6,7-dihydro-3H,5H-pyrrolo-[ 2 , 3- f ] benzimidazol- 6- on 5-ethyl-7,7-dimethyl-2-(4-pyridyl)-6,7-dihydro-3H,5H-pyrrolo-[2,3-f]benzimidazol-6-one

0,73 g (0,06 mol) isonikotinsyre ble oppløst i 30 ml vannfri tetrahydrofuran, tilsatt 0,97 g (0,06 mol) karbonyldiimidazol og omrørt i 1 time ved 30-40°C. Til denne oppløsning ble det dryppet inn en oppløsning av 1,1 g (0,05 mol) 1-etyl-5,6-diamino-3,3-dimetyl-indolin-2-on i 20 ml vannfri tetrahydrofuran, hvorpå blandingen ble omrørt i 3 timer ved romtemperatur. Etter avdestillering av oppløsningsmidlet, ble residuet tilsatt 40 ml 6N saltsyre og omrørt i 8 timer ved 80°C. Oppløsningen ble inndampet betydelig, gjort alkalisk med ammoniakk og ekstrahert 2 ganger med kloroform/etanol = 4:1. Ekstraktet ble vasket og tørket med natriumsulfat og oppløsningsmidlet deretter avdestillert. Residuet ble omkrystallisert fra isopropanol. 0.73 g (0.06 mol) of isonicotinic acid was dissolved in 30 ml of anhydrous tetrahydrofuran, 0.97 g (0.06 mol) of carbonyldiimidazole was added and stirred for 1 hour at 30-40°C. To this solution was added dropwise a solution of 1.1 g (0.05 mol) of 1-ethyl-5,6-diamino-3,3-dimethyl-indolin-2-one in 20 ml of anhydrous tetrahydrofuran, after which the mixture was stirred for 3 hours at room temperature. After distilling off the solvent, 40 ml of 6N hydrochloric acid was added to the residue and stirred for 8 hours at 80°C. The solution was substantially evaporated, made alkaline with ammonia and extracted twice with chloroform/ethanol = 4:1. The extract was washed and dried with sodium sulfate and the solvent then distilled off. The residue was recrystallized from isopropanol.

Utbytte: 0,9 g (58,6% av det teoretiske),Yield: 0.9 g (58.6% of the theoretical),

smeltepunkt: 295-297°Cmelting point: 295-297°C

Eksempel 87 Example 87

5-etyl-2,7,7-trimetyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]-benzimidazol- 6- on x 0, 25 H20 5-ethyl-2,7,7-trimethyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]-benzimidazol-6-one x 0.25 H20

2,92 g (0,01 mol) l-etyl-5,6-diamino-3,3-dimetyl-indolin-2-cn-dihydroklorid ble kokt under tilbakeløpskjøling i 20 ml iseddik i 4 timer. Etter avdestillering av oppløsningsmidlet ble residuet tatt opp i 15 ml metanol, innstillet på pH = 8 med vandig ammoniakk og bragt til et volum på 100 ml med vann. 2.92 g (0.01 mol) of 1-ethyl-5,6-diamino-3,3-dimethyl-indoline-2-cn-dihydrochloride was refluxed in 20 ml of glacial acetic acid for 4 hours. After distilling off the solvent, the residue was taken up in 15 ml of methanol, adjusted to pH = 8 with aqueous ammonia and brought to a volume of 100 ml with water.

Bunnfallet ble suget av, vasket med vann, tørket og omkrystallisert en gang fra etylacetat/diisopropyleter. The precipitate was suctioned off, washed with water, dried and recrystallized once from ethyl acetate/diisopropyl ether.

Utbytte: 1,9 g (76,7% av det teoretiske),Yield: 1.9 g (76.7% of the theoretical),

smeltepunkt: 102-103°Cmelting point: 102-103°C

C14H17N30 x 0,25 H20 (247,81) C14H17N30 x 0.25 H2O (247.81)

Beregnet: C, 67,81; H, 7,12; N, 16,96Calculated: C, 67.81; H, 7.12; N, 16.96

Funnet: C, 67,71; H, 7,22; N, 17,11 Found: C, 67.71; H, 7.22; N, 17,11

Eksempel 88 Example 88

5-etyl-7,7-dimetyl-2-(4-pyridyl)-6,7-dihydro-3H,5H-pyrrolo-[ 2, 3- f] benzimidazol- 6- on 5-ethyl-7,7-dimethyl-2-(4-pyridyl)-6,7-dihydro-3H,5H-pyrrolo-[2,3-f]benzimidazol-6-one

Til en oppløsning av 2,92 g (0,01 mol) l-etyl-5,6-diamino-3,3-dimetyl-indolin-2-on-dihydroklorid i 20 ml etanol og 2 ml iseddik ble det tilsatt 1,07 g (0,01 mol) pyridin-4-aldehyd. To a solution of 2.92 g (0.01 mol) of 1-ethyl-5,6-diamino-3,3-dimethyl-indolin-2-one dihydrochloride in 20 ml of ethanol and 2 ml of glacial acetic acid was added 1, 07 g (0.01 mol) pyridine-4-aldehyde.

Den dyprøde oppløsningen ble oppvarmet i 1 time og etter tilsetning av ytterligere 20 ml etanol, oppvarmet videre til kokepunktet under innledning av luft-oksygen. Etter avdestillering av oppløsningsmidlet ble residuet suspendert i etanol, gjort alkalisk med vandig ammoniakk, hvorpå reaksjonsproduktet ble utfelt ved fortsatt tilsetning av vann. Det ble suget av og omkrystallisert én gang fra isopropanol/diisopropyleter. The deep red solution was heated for 1 hour and after the addition of a further 20 ml of ethanol, further heated to the boiling point under the introduction of air-oxygen. After distilling off the solvent, the residue was suspended in ethanol, made alkaline with aqueous ammonia, whereupon the reaction product was precipitated by continued addition of water. It was suctioned off and recrystallized once from isopropanol/diisopropyl ether.

Utbytte: 1,3 g (42,5% av det teoretiske),Yield: 1.3 g (42.5% of the theoretical),

smeltepunkt: 296-298°Cmelting point: 296-298°C

Eksempel 89 Example 89

5-etyl-7,7-dimetyl-2-(2-metoksy-4-metylsulfinylfenyl) - 6,7-dihydro- 3H, 5H- pyrrolo[ 2, 3- f] benzimidazol- 6- on- hydroklorid 5-Ethyl-7,7-dimethyl-2-(2-methoxy-4-methylsulfinylphenyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one hydrochloride

En oppløsning av 1,9 g (5 mmol) 5-etyl-7,7-dimetyl-2-(2-metoksy-4-metylmerkaptofenyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on i 50 ml kloroform ble under omrøring ved romtemperatur, tilsatt 1,3 g (6 mmol) 80% m-klorperoksybenzosyre, hvoretter omrøringen ble fortsatt i 1 time. Reaksjonsoppløsningen ble vasket med fortynnet natronlut og deretter med vann, inndampet så langt som mulig og renset på en kiselgelsøyle (partikkelstørrelse 40-63 u) og eluert med etylenklorid/etanol (20:1). Ensartede fraksjoner ble samlet og oppløsningsmidlet avdestillert, hvoretter det oljeaktige residuum ble tatt opp i aceton og tilsatt isopropanolisk saltsyre. Det krystallinske bunnfall ble suget av og vasket med aceton og eter. A solution of 1.9 g (5 mmol) of 5-ethyl-7,7-dimethyl-2-(2-methoxy-4-methylmercaptophenyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f ]benzimidazol-6-one in 50 ml of chloroform was added with stirring at room temperature, 1.3 g (6 mmol) of 80% m-chloroperoxybenzoic acid, after which stirring was continued for 1 hour. The reaction solution was washed with dilute sodium hydroxide solution and then with water, evaporated as far as possible and purified on a silica gel column (particle size 40-63 u) and eluted with ethylene chloride/ethanol (20:1). Uniform fractions were collected and the solvent distilled off, after which the oily residue was taken up in acetone and isopropanolic hydrochloric acid was added. The crystalline precipitate was suctioned off and washed with acetone and ether.

Utbytte: 1,4 g (64,5% av det teoretiske),Yield: 1.4 g (64.5% of the theoretical),

smeltepunkt: 253°C (dekomp.)melting point: 253°C (decomp.)

C21<H>24C1N303S (433,97) C21<H>24C1N303S (433.97)

Beregnet: C, 58,12; H, 5,57; N, 9,68Calculated: C, 58.12; H, 5.57; N, 9.68

Funnet: C, 58,33; H, 5,84; N, 9,87 Found: C, 58.33; H, 5.84; N, 9.87

Eksempel 90 Example 90

5-etyl-7,7-dimetyl-2-(4-metylsulfinylfenyl)-6,7-dihydro-3H,5H-pyrrolo[ 2, 3- f] benzimidazol- 6- on x 0, 5 H20 5-ethyl-7,7-dimethyl-2-(4-methylsulfinylphenyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one x 0.5 H20

Fremstillet analogt med Eksempel 89 fra 5-etyl-7,7-dimetyl-2-(4-metylmerkaptofenyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benz-imidazol-6-on og m-klorperbenzosyre. Prepared analogously to Example 89 from 5-ethyl-7,7-dimethyl-2-(4-methylmercaptophenyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benz-imidazol-6-one and m-chloroperbenzoic acid.

Utbytte: 16% av det teoretiske,Yield: 16% of the theoretical,

smeltepunkt: 238°Cmelting point: 238°C

C20H2]N302S x 0,5 H20 (376,47) C20H2]N302S x 0.5 H20 (376.47)

Beregnet: C, 63,81; H, 5,89; N, 11,16Calculated: C, 63.81; H, 5.89; N, 11,16

Funnet: C, 63,65; H, 5,68; N, 10,98 Found: C, 63.65; H, 5.68; N, 10.98

Eksempel 91 Example 91

5-etyl-7,7-dimety1-2-(2-metoksy-4-metylsulfonylfenyl) - 6,7-dihydro- 3H, 5H- pyrrolo[ 2, 3- f] benzimidazol- 6- on- hydroklorid 5-Ethyl-7,7-dimethyl-2-(2-methoxy-4-methylsulfonylphenyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one hydrochloride

En oppløsning av 1,3 g (3,4 mmol) 5-etyl-7,7-dimetyl-2-(2-metoksy-4-metylmerkaptofenyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on i 10 ml maursyre ble tilsatt 1 ml 30% hydrogenperoksyd og omrørt i 1 time ved romtemperatur. Deretter ble blandingen fortynnet med isvann, gjort alkalisk med ammoniakk, hvorpå det utfelte råprodukt ble suget av, tørket, tatt opp i metylenklorid og oppløsningen renset på en kiselgel-søyle (partikkelstørrelse: 40-63 u). Ensartede fraksjoner oppnådd med en blanding av etylenklorid/etanol = 40:1 som elueringsmiddel ble samlet, hvorpå oppløsningsmidlet ble avdestillert og det klebrige residuum tatt opp i etylacetat og tilsatt isopropanolisk saltsyre. Bunnfallet ble suget av og vasket med aceton og eter. A solution of 1.3 g (3.4 mmol) of 5-ethyl-7,7-dimethyl-2-(2-methoxy-4-methylmercaptophenyl)-6,7-dihydro-3H,5H-pyrrolo[2,3 -f]benzimidazol-6-one in 10 ml of formic acid was added to 1 ml of 30% hydrogen peroxide and stirred for 1 hour at room temperature. The mixture was then diluted with ice water, made alkaline with ammonia, whereupon the precipitated crude product was suctioned off, dried, taken up in methylene chloride and the solution purified on a silica gel column (particle size: 40-63 u). Uniform fractions obtained with a mixture of ethylene chloride/ethanol = 40:1 as eluent were collected, whereupon the solvent was distilled off and the sticky residue taken up in ethyl acetate and isopropanolic hydrochloric acid added. The precipitate was suctioned off and washed with acetone and ether.

Utbytte: 1,5 g (97,8% av det teoretiske),Yield: 1.5 g (97.8% of the theoretical),

smeltepunkt: fra 255°C (dekomp.)melting point: from 255°C (decomp.)

C21H24C1N304S (449,95) C21H24C1N304S (449.95)

Beregnet: C, 56,06; H, 5,38; N, 9,34Calculated: C, 56.06; H, 5.38; N, 9.34

Funnet: C, 56,25; H, 5,41; N, 9,26 Found: C, 56.25; H, 5.41; N, 9.26

Eksempel 92 Example 92

5-etyl-7,7-dimetyl-2-(4-metylsulfonylfenyl)-6,7-dihydro-3H,5H-pyrrolo[ 2 , 3- f jbenzimidazol- 6- on 5-ethyl-7,7-dimethyl-2-(4-methylsulfonylphenyl)-6,7-dihydro-3H,5H-pyrrolo[ 2 , 3- f jbenzimidazol- 6- one

Fremstillet analogt med Eksempel 91 fra 5-etyl-7,7-dimetyl-2-(4-metylmerkaptofenyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on og hydrogenperoksyd. Prepared analogously to Example 91 from 5-ethyl-7,7-dimethyl-2-(4-methylmercaptophenyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one and hydrogen peroxide.

Utbytte: 62% av det teoretiske,Yield: 62% of the theoretical,

smeltepunkt: 262°Cmelting point: 262°C

C20<H>21<N>303S (383,47) C20<H>21<N>303S (383.47)

Beregnet: C, 62,64; H, 5,52; N, 10,96Calculated: C, 62.64; H, 5.52; N, 10.96

Funnet: C, 62,56; H, 5,76; N, 11,14 Found: C, 62.56; H, 5.76; N, 11,14

Eksempel 93 Example 93

2-(4-acetamidofenyl)-5-etyl-7,7-dimetyl-6,7-dihydro-3H,5H-pyrrolo[ 2, 3- f] benzimidazol- 6- on x H20 8 g (25 mmol) 5-etyl-2-(4-aminofenyl)-7,7-dimetyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on ble tilsatt 10 ml acetanhydrid og omrørt i 2 timer ved romtemperatur. Den derved oppnådde orange-farvede grøtaktige masse ble utgnidd med etylacetat, suget av og kromatografert på en kiselgelsøyle (partikkelstørrelse: 40-63 u, elueringsmiddel: etylenklorid/etylacetat/etanol = 5:5:1).Ensartede fraksjoner ble samlet, oppløsningsmidlet avdestillert, residuet rørt opp med etylacetat og suget av. 2-(4-acetamidophenyl)-5-ethyl-7,7-dimethyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one x H20 8 g (25 mmol) 5 -ethyl-2-(4-aminophenyl)-7,7-dimethyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one was added to 10 ml of acetic anhydride and stirred for 2 hours at room temperature. The resulting orange-coloured mushy mass was rubbed with ethyl acetate, sucked off and chromatographed on a silica gel column (particle size: 40-63 µ, eluent: ethylene chloride/ethyl acetate/ethanol = 5:5:1). Uniform fractions were collected, the solvent distilled off , the residue stirred up with ethyl acetate and suctioned off.

Utbytte: 4 g (42,1% av det teoretiske),Yield: 4 g (42.1% of the theoretical),

smeltepunkt: > 290°Cmelting point: > 290°C

C21H22N402x H20 (380,45) C21H22N402x H20 (380.45)

Beregnet: C, 66,30; H, 6,36; N, 14,73Calculated: C, 66.30; H, 6.36; N, 14.73

Funnet: C, 66,47; H, 6,10; N, 14,71 Found: C, 66.47; H, 6.10; N, 14.71

Eksempel 94 Example 94

5-etyl-7,7-dimetyl-2-(4-piperidinyl)-6,7-dihydro-3H,5H-pyrrolo[ 2<3- f] benzimidazol- 6- on x 0, 5 H20 5-ethyl-7,7-dimethyl-2-(4-piperidinyl)-6,7-dihydro-3H,5H-pyrrolo[2<3-f]benzimidazol-6-one x 0.5 H20

1,02 g (3,3 mmol) 5-etyl-7,7-dimetyl-2-(4-pyridyl)-6 , 7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on ble oppløst i 100 ml iseddik, tilsatt 0,2 g platinaoksyd og hydrert i en autoklav ved romtemperatur i 6 timer under 3 bar hydrogentrykk. Katalysatoren ble suget av, filtratet inndampet og residuet oppløst i 15 ml vann som deretter ble mettet med kaliumkarbonat og ekstrahert med kloroform.Kloroformfasen ble vasket med mettet koksaltoppløsning, tørket med natriumsulfat og opp-løsningsmidlet avdestillert. Det faste residuet ble omkrystallisert én gang fra etylacetat/eter. 1.02 g (3.3 mmol) 5-ethyl-7,7-dimethyl-2-(4-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazole-6- was dissolved in 100 ml of glacial acetic acid, 0.2 g of platinum oxide was added and hydrated in an autoclave at room temperature for 6 hours under 3 bar hydrogen pressure. The catalyst was sucked off, the filtrate evaporated and the residue dissolved in 15 ml of water which was then saturated with potassium carbonate and extracted with chloroform. The chloroform phase was washed with saturated sodium chloride solution, dried with sodium sulphate and the solvent distilled off. The solid residue was recrystallized once from ethyl acetate/ether.

Utbytte: 0,8 g (74,8% av det teoretiske),Yield: 0.8 g (74.8% of the theoretical),

smeltepunkt: 141-142°Cmelting point: 141-142°C

C18H24N40 x 0,5 H20 (321,43) C18H24N40 x 0.5 H2O (321.43)

Beregnet: C, 67,26; H, 7,84; N, 17,43Calculated: C, 67.26; H, 7.84; N, 17.43

Funnet: C, 67,35; H, 8,05; N, 17,21 Found: C, 67.35; H, 8.05; N, 17,21

Eksempel 95 Example 95

5-etyl-7,7-dimetyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f ]-benzimidazol- 6- on- hydroklorid x 0, 5 H20 5-ethyl-7,7-dimethyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]-benzimidazol-6-one hydrochloride x 0.5 H20

Fremstillet analogt med Eksempel 87 fra l-etyl-5,6-diamino-3,3-dimetyl-indolin-2-on og maursyre. Prepared analogously to Example 87 from 1-ethyl-5,6-diamino-3,3-dimethyl-indolin-2-one and formic acid.

Utbytte: 80% av det teoretiske,Yield: 80% of the theoretical,

smeltepunkt: 250-252°Cmelting point: 250-252°C

C13H16C1N30 x 0,5 H20 ( 265,75 ) C13H16C1N30 x 0.5 H20 ( 265.75 )

Beregnet: C, 56,83; H, 6,24; N, 15,29Calculated: C, 56.83; H, 6.24; N, 15,29

Funnet: C, 57,09; H, 6,45; N, 15,44 Found: C, 57.09; H, 6.45; N, 15.44

Eksempel 96 Example 96

2-(4-pyridyl)-3,5,7,7-tetrametyl-6,7-dihydro-3H,5H-pyrrolo-[ 2 , 3- f ] benzimidazol- 6- on 2-(4-pyridyl)-3,5,7,7-tetramethyl-6,7-dihydro-3H,5H-pyrrolo-[2,3-f]benzimidazol-6-one

Fremstillet analogt med Eksempel 1 fra 5-nitro-6-(N-metyl-isonikotinoylamido) -1 , 3,3-trimetyl-indolin-2-on. Prepared analogously to Example 1 from 5-nitro-6-(N-methyl-isonicotinoylamido)-1,3,3-trimethyl-indolin-2-one.

Utbytte: 77% av det teoretiske,Yield: 77% of the theoretical,

smeltepunkt: 218-2l9°C (etylacetat/diisopropyleter)melting point: 218-219°C (ethyl acetate/diisopropyl ether)

C18<H>18N40 (306,37) C18<H>18N40 (306.37)

Beregnet: C, 70,57; H, 5,92; N, 18,29Calculated: C, 70.57; H, 5.92; N, 18,29

Funnet: C, 7 0,40; H, 5,94; N, 18,3 2 Found: C, 7 0.40; H, 5.94; N, 18.3 2

Eksempel 97 Example 97

5-metyl-2-(4-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]-benzimidazol- 6- on x 0, 5 H20 5-methyl-2-(4-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]-benzimidazol-6-one x 0.5 H2O

Fremstillet analogt med Eksempel 1 fra 5-isonikotinoylamido-l-metyl-6-nitro-indolin-22-on. Prepared analogously to Example 1 from 5-isonicotinoylamido-1-methyl-6-nitro-indolin-22-one.

Utbytte: 65% av det teoretiske,Yield: 65% of the theoretical,

smeltepunkt: > 290°C (isopropanol)melting point: > 290°C (isopropanol)

C15H12N40 x 0,5 H20 (273,29) C15H12N40 x 0.5 H2O (273.29)

Beregnet: C, 65,92; H, 4,79; N, 20,50Calcd: C, 65.92; H, 4.79; N, 20.50

Funnet: C, 65,74; H, 4,90; N, 20,59 Found: C, 65.74; H, 4.90; N, 20.59

Eksempel 98 Example 98

7,7-dimetyl-2-(4-metylmerkaptofenyl)-5-n-pentyl-6,7-dihydro-3H, 5H- pyrrolo[ 2, 3- f] benzimidazol- 6- on x 0, 6 H20 7,7-dimethyl-2-(4-methylmercaptophenyl)-5-n-pentyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one x 0.6H20

Fremstillet analogt med Eksempel 1 fra 3,3-dimetyl-5-(4-metylmerkapto-benzoylamido)-6-nitro-l-n-pentyl-indolin-2-on. Utbytte: 58% av det teoretiske, Prepared analogously to Example 1 from 3,3-dimethyl-5-(4-methylmercapto-benzoylamido)-6-nitro-1-n-pentyl-indolin-2-one. Yield: 58% of the theoretical,

smeltepunkt: 244°C (etylacetat/isopropanol)melting point: 244°C (ethyl acetate/isopropanol)

C23H27N30S x 0,6 H20 (404,35) C23H27N30S x 0.6 H2O (404.35)

Beregnet: C, 68,32; H, 7,03; N, 10,39Calculated: C, 68.32; H, 7.03; N, 10.39

Funnet: C, 68,11; H, 7,05; N, 10,27 Found: C, 68.11; H, 7.05; N, 10.27

Eksempel 99 Example 99

7,7-dimetyl-2-(4-metylsulfonylfenyl)-5-n-pentyl-6,7-dihydro-3H, 5H- pyrrolo[ 2, 3- f] benzimidazol- 6- on x H20 7,7-dimethyl-2-(4-methylsulfonylphenyl)-5-n-pentyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one x H20

Fremstillet analogt med Eksempel 91 fra 7,7-dimetyl-2-(4-metylmerkaptofenyl)-5-n-pentyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on og hydrogenperoksyd. Prepared analogously to Example 91 from 7,7-dimethyl-2-(4-methylmercaptophenyl)-5-n-pentyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one and hydrogen peroxide.

Utbytte: 51,5% av det teoretiske,Yield: 51.5% of the theoretical,

smeltepunkt: 267°Cmelting point: 267°C

C23H27N303S x H20 (443,56) C23H27N303S x H20 (443.56)

Beregnet: C, 62,28; H, 6,59; N, 9,47Calculated: C, 62.28; H, 6.59; N, 9.47

Funnet: C, 62,11; H, 6,39; N, 9,20 Found: C, 62.11; H, 6.39; N, 9.20

Eksempel 100 Example 100

5-etyl-7,7-dimetyl-2-(2-pyrrolyl)-6,7-dihydro-3H,5H-pyrrolo-[ 2 , 3- f ] benzimidazol- 6- on 5-ethyl-7,7-dimethyl-2-(2-pyrrolyl)-6,7-dihydro-3H,5H-pyrrolo-[2,3-f]benzimidazol-6-one

Fremstillet analogt med Eksempel 78 fra pyrrol-2-karbonsyre og l-etyl-5,6-diamino-3,3-dimetyl-indolin-2-on. Prepared analogously to Example 78 from pyrrole-2-carboxylic acid and 1-ethyl-5,6-diamino-3,3-dimethyl-indolin-2-one.

Utbytte: 17,5% av det teoretiske,Yield: 17.5% of the theoretical,

smeltepunkt: > 290°Cmelting point: > 290°C

C17H19C1N40 (330,82) C17H19C1N40 (330.82)

Beregnet: C, 61,72; H, 5,79; N, 16,94; Cl, 10,72 Calculated: C, 61.72; H, 5.79; N, 16.94; Cl, 10.72

Funnet: C, 61,44; H, 5,92; N, 16,70; Cl, 10,53 Found: C, 61.44; H, 5.92; N, 16.70; Cl, 10.53

Eksempel 101 Example 101

7,7-dimetyl-5-(2-metoksyetyl)-2-(5-metyl-3-furyl)-6,7-dihydro-3H, 5H- pyrrolo[ 2, 3- f] benzimidazol- 6- on 7,7-dimethyl-5-(2-methoxyethyl)-2-(5-methyl-3-furyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one

Fremstillet analogt med Eksempel 1 fra 3,3-dimetyl-l-(2-metoksyetyl)-5-(5-metyl-3-furoylamido)-6-nitro-indolin-2-on. Utbytte: 46,4% av det teoretiske, Prepared analogously to Example 1 from 3,3-dimethyl-1-(2-methoxyethyl)-5-(5-methyl-3-furoylamido)-6-nitro-indolin-2-one. Yield: 46.4% of the theoretical,

smeltepunkt: 254-256°C (etylacetat)melting point: 254-256°C (ethyl acetate)

C19<H>21<N>303( 339, 39) C19<H>21<N>303( 339, 39)

Beregnet: C, 67,24; H, 6,24; N, 12,38Calculated: C, 67.24; H, 6.24; N, 12.38

Funnet: C, 67,22; H, 6,35; N, 12,45 Found: C, 67.22; H, 6.35; N, 12.45

Eksempel 102 Example 102

5-etyl-7,7-dimetyl-2-(5-metyl-3-furyl)-6,7-dihydro-3H,5H-pyrrolo[ 2 , 3- f ] benzimidazol- 6- on 5-ethyl-7,7-dimethyl-2-(5-methyl-3-furyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one

Fremstillet analogt med Eksempel 1 fra l-etyl-3,3-dimetyl-5-(5-metyl-3-furoylamido)-6-nitro-indolin-2-on. Prepared analogously to Example 1 from 1-ethyl-3,3-dimethyl-5-(5-methyl-3-furoylamido)-6-nitro-indolin-2-one.

Utbytte: 56,6% av det teoretiske,Yield: 56.6% of the theoretical,

smeltepunkt: 276-278°Cmelting point: 276-278°C

C18<H>19<N>3<0>2(309,37 ) C18<H>19<N>3<0>2(309.37 )

Beregnet: C, 69,88; H, 6,19; N, 13,58Calcd: C, 69.88; H, 6.19; N, 13.58

Funnet: C, 69,74; H, 6,19; N, 13,48 Found: C, 69.74; H, 6.19; N, 13.48

Eksempel 103 Example 103

7,7-dimetyl-5-isopropyl-2-(5-metyl-3-furyl)-6,7-dihydro-3H,5H-pyrrolo[ 2 , 3- f ] benzimidazol- 6- on 7,7-dimethyl-5-isopropyl-2-(5-methyl-3-furyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one

Fremstillet analogt med Eksempel 1 fra 3,3-dimetyl-l-isopropyl-5-(5-metyl-3-furoylamido)-6-nitro-indolin-2-on. Utbytte: 69% av det teoretiske, Prepared analogously to Example 1 from 3,3-dimethyl-1-isopropyl-5-(5-methyl-3-furoylamido)-6-nitro-indolin-2-one. Yield: 69% of the theoretical,

smeltepunkt: > 290°Cmelting point: > 290°C

C19<H>21N302(323 , 39) C19<H>21N302(323 , 39)

Beregnet: C, 70,57; H, 6,55; N, 12,99Calculated: C, 70.57; H, 6.55; N, 12.99

Funnet: C, 70,68; H, 6,64; N, 13,07 Found: C, 70.68; H, 6.64; N, 13.07

Eksempel 104 Example 104

7,7-dimetyl-2-(4-metyl-sulfinylfenyl)-5-n-pentyl-6,7-dihydro-3H, 5H- pyrrolo[ 2, 3- f] benzimidazol- 6- on 7,7-dimethyl-2-(4-methyl-sulfinylphenyl)-5-n-pentyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one

Fremstillet analogt med Eksempel 89 fra 7,7-dimetyl-2-(4-metylmerkaptofenyl)-5-n-pentyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on. Prepared analogously to Example 89 from 7,7-dimethyl-2-(4-methylmercaptophenyl)-5-n-pentyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one.

Utbytte: 61% av det teoretiske,Yield: 61% of the theoretical,

smeltepunkt: 235°Cmelting point: 235°C

C23<H>27<N>302S (409, 55 ) C23<H>27<N>302S (409, 55 )

Beregnet: C, 67,45; H, 6,65; N, 10,26; S, 7,83 Calculated: C, 67.45; H, 6.65; N, 10.26; S, 7.83

Funnet: C, 67,43; H, 6,75; N, 10,12; S, 7,58 Found: C, 67.43; H, 6.75; N, 10.12; S, 7.58

Eksempel 105 Example 105

7,7-dimetyl-2-(5-metyl-3-furyl)-5-n-pentyl-6,7-dihydro-3H, 5H- pyrrolo[ 2, 3- f] benzimidazol- 6- on 7,7-dimethyl-2-(5-methyl-3-furyl)-5-n-pentyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one

Fremstillet analogt med Eksempel 1 fra 3,3-dimetyl-5-(5-metyl-3-furoylamido)-6-nitro-l-n-pentyl-indolin-2-on. Utbytte: 48,5% av det teoretiske, Prepared analogously to Example 1 from 3,3-dimethyl-5-(5-methyl-3-furoylamido)-6-nitro-1-n-pentyl-indolin-2-one. Yield: 48.5% of the theoretical,

smeltepunkt: 210-212°Cmelting point: 210-212°C

C21<H>25N302(351, 45 ) C21<H>25N302(351, 45 )

Beregnet: C, 71,77; H, 7,17; N, 11,96Calculated: C, 71.77; H, 7.17; N, 11.96

Funnet: C, 71,76; H, 7,22; N, 12,04 Found: C, 71.76; H, 7.22; N, 12.04

Eksempel 106 Example 106

5-etyl-7,7-dimetyl-2-fenyl-6,7-dihydro-3H,5H-pyrrolo-[ 2, 3- f] benzimidazol- 6- on 5-ethyl-7,7-dimethyl-2-phenyl-6,7-dihydro-3H,5H-pyrrolo-[2,3-f]benzimidazol-6-one

Fremstillet analogt med Eksempel 1 fra l-etyl-5-benzoyl-amido-3,3-dimetyl-6-nitro-indolin-2-on. Prepared analogously to Example 1 from 1-ethyl-5-benzoyl-amido-3,3-dimethyl-6-nitro-indolin-2-one.

Utbytte: 63% av det teoretiske,Yield: 63% of the theoretical,

smeltepunkt: 308°C (dekomp.)melting point: 308°C (decomp.)

C19<H>19N30 (305,38) C19<H>19N30 (305.38)

Beregnet: C, 74,73; H, 6,27; N, 13,76Calculated: C, 74.73; H, 6.27; N, 13.76

Funnet: C, 74,54; H, 6,30; N, 13,74 Found: C, 74.54; H, 6.30; N, 13.74

Eksempel 107 Example 107

5-etyl-7,7-dimetyl-2-n-propyl-6,7-dihydro-3H,5H-pyrrolo-[ 2, 3- f] benzimidazol- 6- on 5-ethyl-7,7-dimethyl-2-n-propyl-6,7-dihydro-3H,5H-pyrrolo-[2,3-f]benzimidazol-6-one

Fremstillet analogt med Eksempel 1 fra l-etyl-5-butyryl-amido-3,3-dimetyl-6-nitro-indolin-2-on. Prepared analogously to Example 1 from 1-ethyl-5-butyryl-amido-3,3-dimethyl-6-nitro-indolin-2-one.

Utbytte: 30% av det teoretiske,Yield: 30% of the theoretical,

Rf-verdi: 0,47 (kiselgel, etylenklorid/etanol = 9:1) C16<H>21N30 x 0,85 CHC13(370,71) Rf value: 0.47 (silica gel, ethylene chloride/ethanol = 9:1) C16<H>21N30 x 0.85 CHC13(370.71)

Beregnet: C, 54,59; H, 5,94; N, 11,34Calculated: C, 54.59; H, 5.94; N, 11.34

Funnet: C, 54,44; H, 6,04; N, 11,25 Found: C, 54.44; H, 6.04; N, 11.25

Eksempel 108 Example 108

5- etyl-7,7-dimetyl-2-(2-tienylmetyl)-6,7-dihydro-3H,5H-pyrrolo[ 2, 3- f] benzimidazol- 6- on x 0, 6 H20 5- ethyl-7,7-dimethyl-2-(2-thienylmethyl)-6,7-dihydro-3H,5H-pyrrolo[ 2, 3-f] benzimidazol- 6-one x 0.6 H20

Fremstillet analogt med Eksempel 1 fra l-etyl-3,3-dimetyl-6- nitro-5-(2-tienylacetamido)-indolin-2-on. Prepared analogously to Example 1 from 1-ethyl-3,3-dimethyl-6-nitro-5-(2-thienylacetamido)-indolin-2-one.

Utbytte: 50,7% av det teoretiske,Yield: 50.7% of the theoretical,

smeltepunkt: fra 115°Cmelting point: from 115°C

C18H19N30S x 0,6 H20 (336,24) C18H19N30S x 0.6 H2O (336.24)

Beregnet: C, 64,30; H, 6,06; N, 12,50; S, 9,53 Calculated: C, 64.30; H, 6.06; N, 12.50; S, 9.53

Funnet: C, 64,53; H, 6,27; N, 12,28; S, 9,32 Found: C, 64.53; H, 6.27; N, 12.28; S, 9.32

Eksempel 109 Example 109

5- etyl-7,7-dimetyl-2-(3-tienylmetyl)-6,7-dihydro-3H,5H-pyrrolo[ 2 , 3- f ] benzimidazol- 6- on 5-ethyl-7,7-dimethyl-2-(3-thienylmethyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one

Fremstillet analogt med Eksempel 1 fra l-etyl-3,3-dimetyl-6- nitro-5-(3-tienylacetamido)-indolin-2-on. Prepared analogously to Example 1 from 1-ethyl-3,3-dimethyl-6-nitro-5-(3-thienylacetamido)-indolin-2-one.

Utbytte: 46,2% av det teoretiske,Yield: 46.2% of the theoretical,

smeltepunkt: fra 105°Cmelting point: from 105°C

C18<H>19N30S (325,44) C18<H>19N30S (325.44)

Beregnet: C, 66,43; K, 5,88; N, 12,91; S, 9,85 Calculated: C, 66.43; K, 5.88; N, 12.91; S, 9.85

Funnet: C, 66,27; H, 6,00; N, 12,74; S, 9,68 Found: C, 66.27; H, 6.00; N, 12.74; S, 9.68

Eksempel 110 Example 110

7,7-dimetyl-5-(2-hydroksyetyl)-2-(3-pyridyl) -6,7-dihydro-3H, 5H- pyrrolo[ 2, 3- f] benzimidazol- 6- on 7,7-dimethyl-5-(2-hydroxyethyl)-2-(3-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one

Fremstillet analogt med Eksempel 10 fra 7,7-dimetyl-5-(2-metoksyetyl)-2-(3-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on og bortribromid. Prepared analogously to Example 10 from 7,7-dimethyl-5-(2-methoxyethyl)-2-(3-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazole-6- on and boron tribromide.

Utbytte: 52,7% av det teoretiske,Yield: 52.7% of the theoretical,

smeltepunkt: 285-286°Cmelting point: 285-286°C

C18<H>18N402( 322, 37 ) C18<H>18N402( 322, 37 )

Beregnet: C, 67,07; H, 5,63; N, 17,38Calculated: C, 67.07; H, 5.63; N, 17.38

Funnet: C, 66,80; H, 5,76; N, 17,29 Found: C, 66.80; H, 5.76; N, 17.29

Eksempel 111 Example 111

5-n-butyl-7,7-dimetyl-2-(2-tienylmetyl)-6,7-dihydro-3H, 5H-pyrrolo[ 2, 3- f] benzimidazol- 6- on 5-n-butyl-7,7-dimethyl-2-(2-thienylmethyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one

Fremstillet analogt med Eksempel 1 fra l-n-butyl-3,3-dimetyl-6-nitro-5-(2-tienylacetamido)-indolin-2-on. Utbytte: 13,7% av det teoretiske, Prepared analogously to Example 1 from 1-n-butyl-3,3-dimethyl-6-nitro-5-(2-thienylacetamido)-indolin-2-one. Yield: 13.7% of the theoretical,

smeltepunkt: fra 70°Cmelting point: from 70°C

C20<H>23N30S (353,48) C20<H>23N30S (353.48)

Beregnet: C, 67,96; H, 6,56; N, 11,89; S, 9,07 Calcd: C, 67.96; H, 6.56; N, 11.89; S, 9.07

Funnet: C, 67,83; H, 6,78; N, 12,04; S, 8,92 Found: C, 67.83; H, 6.78; N, 12.04; S, 8.92

Eksempel 112 Example 112

5-n-butyl-7,7-dimetyl-2-(3-tienyl-metyl)-6,7-dihydro-3H,5H-pyrrolo[ 2, 3- f] benzimidazol- 6- on 5-n-butyl-7,7-dimethyl-2-(3-thienyl-methyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one

Fremstillet analogt med Eksempel 1 fra l-n-butyl-3,3-dimetyl-6-nitro-5-(3-tienyl-acetamido)-indolin-2-on. Prepared analogously to Example 1 from 1-n-butyl-3,3-dimethyl-6-nitro-5-(3-thienyl-acetamido)-indolin-2-one.

Utbytte: 53,0% av det teoretiske,Yield: 53.0% of the theoretical,

smeltepunkt: 118-120°Cmelting point: 118-120°C

C20<H>23N3OS (353,48) C20<H>23N3OS (353.48)

Beregnet: C, 67,96; H, 6,56; N, 11,89; S, 9,07 Calcd: C, 67.96; H, 6.56; N, 11.89; S, 9.07

Funnet: C, 67,76; H, 6,62; N, 11,98; S, 8,90 Found: C, 67.76; H, 6.62; N, 11.98; S, 8.90

Eksempel 113 Example 113

5-n-butyl-7,7-dimetyl-2-(2-tienyl)-6,7-dihydro-3H,5H-pyrrolo[ 2 , 3- f ] benzimidazol- 6- on 5-n-butyl-7,7-dimethyl-2-(2-thienyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one

Fremstillet analogt med Eksempel 1 fra l-n-butyl-3,3-dimetyl-6-nitro-5-(2-tenoylamido)-indolin-2-on. Prepared analogously to Example 1 from 1-n-butyl-3,3-dimethyl-6-nitro-5-(2-thenoylamido)-indolin-2-one.

Utbytte: 94,5% av det teoretiske,Yield: 94.5% of the theoretical,

smeltepunkt: 271°C (etylacetat/etanol)melting point: 271°C (ethyl acetate/ethanol)

C19<H>21N3OS (339,45) C19<H>21N3OS (339.45)

Beregnet: C, 67,23; H, 6,24; N, 12,38Calculated: C, 67.23; H, 6.24; N, 12.38

Funnet: C, 67,18; H, 6,26; N, 12,32 Found: C, 67.18; H, 6.26; N, 12.32

Eksempel 114 Example 114

7,7-dimetyl-2-(4-metylsulfinylfenyl)-5-n-propyl-6,7-dihydro-3H, 5H- pyrrolo [ 2 , 3- f ] benzimidazol- 6- on 7,7-dimethyl-2-(4-methylsulfinylphenyl)-5-n-propyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one

Fremstillet analogt med Eksempel 89 fra 7,7-dimetyl-2-(4-metylmerkaptofenyl)-5-n-propyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on og m-klorperbenzosyre. Prepared analogously to Example 89 from 7,7-dimethyl-2-(4-methylmercaptophenyl)-5-n-propyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one and m-chloroperbenzoic acid.

Utbytte: 65,6% av det teoretiske,Yield: 65.6% of the theoretical,

smeltepunkt: 242°Cmelting point: 242°C

C21H23N302S x 0,2 H20 (385,09) C21H23N302S x 0.2 H2O (385.09)

Beregnet: C, 65,50; H, 6,12; N, 10,91; S, 8,33 Calculated: C, 65.50; H, 6.12; N, 10.91; S, 8.33

Funnet: C, 65,66; H, 6,12; N, 10,83; S, 8,15 Found: C, 65.66; H, 6.12; N, 10.83; S, 8.15

Eksempel 115 Example 115

7,7-dimetyl-2-(4-metylsulfonylfenyl)-5-n-propyl-6,7-dihydro-3H, 5H- pyrrolo[ 2, 3- f] benzimidazol- 6- on 7,7-Dimethyl-2-(4-methylsulfonylphenyl)-5-n-propyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one

Fremstillet analogt med Eksempel 91 fra 7,7-dimetyl-2-(4-metylmerkaptofenyl)-5-n-propyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-on og hydrogenperoksyd. Prepared analogously to Example 91 from 7,7-dimethyl-2-(4-methylmercaptophenyl)-5-n-propyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one and hydrogen peroxide.

Utbytte: 55,4% av det teoretiske,Yield: 55.4% of the theoretical,

smeltepunkt: 273-275°Cmelting point: 273-275°C

C2i<H>23<N>303S (397,49) C2i<H>23<N>303S (397.49)

Beregnet: C, 63,46; H, 5,83; N, 10,57; S, 8,07 Calcd: C, 63.46; H, 5.83; N, 10.57; S, 8.07

Funnet: C, 63,30; H, 5,91; N, 10,37; S, 8,11 Found: C, 63.30; H, 5.91; N, 10.37; S, 8,11

Claims (2)

1. Analogifremgangsmåte for fremstilling av terapeutisk aktive pyrrolo-benzimidazoler med formel 1. Analogous method for the preparation of therapeutically active pyrrolo-benzimidazoles of formula hvor A og B sammen med de to mellomliggende karbonatomer utgjør en imidazogruppe med formel where A and B together with the two intermediate carbon atoms form an imidazo group with formula hvor Rx er et hydrogenatom eller en eventuelt med en fenylgruppe substituert alkylgruppe med 1-3 karbonatomer og R2 er et hydrogenatom, en eventuelt med en fenyl-, pyridyl- eller tienylgruppe substituert alkylgruppe, en vinylengruppe som terminalt er substituert med en fenyl- eller pyridylgruppe, en eventuelt med et halogenatom, en hydroksy-, alkoksy-, merkapto-, alkylmerkapto-, alkylsulfinyl-, alkylsulfonyl-, cyano-, amino-, alkylamino-, dialkylamino-, alkanoylamino- eller nitrogruppe substituert fenylgruppe, hvor en hydroksyfenylgruppe dessuten kan være substituert med én eller to alkylgrupper som hver har 1- 4 karbonatomer, eller hvor en aminofenylgruppe kan være substituert med ett eller to halogenatomer, en med halogenatomer, hydroksy-, alkoksy-, merkapto-, alkylmerkapto-, alkylsulfinyl-eller alkylsulfonylgrupper disubstituert fenylgruppe, hvor substituentene i fenylkjernen kan være like eller forskjellige, en via et karbonatom bundet 5- eller 6-leddet heteroaromatisk ring som inneholder et oksygen-, svovel- eller nitrogenatom, to eller tre nitrogenatomer eller ett nitrogenatom og ett oksygen-eller svovelatom, hvortil én eller to 1,4-butadienylgrupper kan være tilknyttet via to nabostilte karbonatomer, idet bindingen i dette tilfelle også kan skje via en tilkondensert fenylring, og, når det gjelder pyridinene, disse ytterligere kan være substituert med en amino-, alkylamino-, dialkylamino-, alkanoylamino- eller morfolinogruppe, eller med to halogenatomer eller med ett halogenatom og én amino- eller morfolinogruppe, og når det gjelder kinolinene, disse ytterligere kan være mono- eller disubstituert med et halogenatom, en alkoksy- eller fenylgruppe, idet substituentene kan være like eller forskjellige, en via et karbonatom bundet 5- til 7-leddet mettet imino-, N-alkylimino-eller N-alkanoylimino-alkylenring, en 1,2,3,4-tetrahydrokinolyl-eller 5,6,7,8-tetrahydrokinolylgruppe, hvor alle ovenfor ved definisjon av resten R2 nevnte ringer kan være substituert med en alkylgruppe, og alkyldelen av alle ovenfor nevnte grupper, om intet annet er angitt, hver kan inneholde 1-3 karbonatomer og alkanoyldelen 2 eller 3 karbonatomer, R3 er en eventuelt med en fenylgruppe substituert alkylgruppe, en alkylgruppe med 4-6 karbonatomer eller en alkylgruppe som fra 2- stillingen av, er substituert med en hydroksy-, alkoksy-eller pyridiniumgruppe, hvor hver alkyldel kan inneholde 1-3 karbonatomer, R4 og R5 , som kan være like eller forskjellige, er hydrogenatomer, alkylgrupper med 1-3 karbonatomer eller cykloalkylgrupper med 3-7 karbonatomer, og deres syreaddisjonssalter, karakterisert ved ata) en forbindelse med formel where Rx is a hydrogen atom or an optionally substituted by a phenyl group alkyl group with 1-3 carbon atoms and R2 is a hydrogen atom, an optionally substituted alkyl group with a phenyl, pyridyl or thienyl group, a vinylene group which is terminally substituted with a phenyl or pyridyl group, an optionally with a halogen atom, a hydroxy-, alkoxy-, mercapto-, alkylmercapto- , alkylsulfinyl-, alkylsulfonyl-, cyano-, amino-, alkylamino-, dialkylamino-, alkanoylamino- or nitro group substituted phenyl group, where a hydroxyphenyl group may also be substituted by one or two alkyl groups each having 1-4 carbon atoms, or where an aminophenyl group can be substituted with one or two halogen atoms, a disubstituted phenyl group with halogen atoms, hydroxy, alkoxy, mercapto, alkylmercapto, alkylsulfinyl or alkylsulfonyl groups, where the substituents in the phenyl nucleus can be the same or different, a 5- or 6-membered heteroaromatic ring containing one oxygen, sulfur or nitrogen atom, two or three nitrogen atoms or one nitrogen atom and one oxygen n-or sulfur atom, to which one or two 1,4-butadienyl groups can be attached via two adjacent carbon atoms, as the bond in this case can also take place via a fused phenyl ring, and, in the case of the pyridines, these can further be substituted with an amino -, alkylamino, dialkylamino, alkanoylamino or morpholino group, or with two halogen atoms or with one halogen atom and one amino or morpholino group, and in the case of the quinolines, these may further be mono- or disubstituted with a halogen atom, an alkoxy or phenyl group, in that the substituents can be the same or different, a 5- to 7-membered saturated imino-, N-alkylimino- or N-alkanoylimino-alkylene ring linked via a carbon atom, a 1,2,3,4-tetrahydroquinolyl-or 5, 6,7,8-tetrahydroquinolyl group, where all the rings mentioned above in the definition of the residue R2 can be substituted with an alkyl group, and the alkyl part of all the groups mentioned above, unless otherwise stated, each can contain 1-3 carbons atoms and the alkanoyl part 2 or 3 carbon atoms, R3 is an alkyl group optionally substituted with a phenyl group, an alkyl group with 4-6 carbon atoms or an alkyl group which, from the 2-position onwards, is substituted with a hydroxy, alkoxy or pyridinium group, where each alkyl part can contain 1-3 carbon atoms, R 4 and R 5 , which may be the same or different, are hydrogen atoms, alkyl groups with 1-3 carbon atoms or cycloalkyl groups with 3-7 carbon atoms, and their acid addition salts, characterized by ata) a compound of formula hvor R3 til R5 er som ovenfor definert, én av restene A_ eller B_ betyr en R^ NH-gruppe, hvor Rx er som ovenfor definert, og den andre av restene Ax eller Bx betyr en where R3 to R5 are defined as above, one of the residues A_ or B_ means an R^ NH group, where Rx is as defined above, and the other of the residues Ax or Bx means a -gruppe, hvor R2 er som ovenfor definert og R6 er et hydrogenatom eller, dersom R_ utgjør et hydrogenatom, en eventuelt med en fenylgruppe substituert alkylgruppe med 1-3 karbonatomer, Z_ og Z2 , som kan være like eller forskjellige, betyr nukleofile utgående grupper, som eventuelt substituerte amino-, alkoksy-, fenylalkoksy-, fenoksy-, alkylmerkapto-, fenylalkylmerkapto-eller fenyltiogrupper, eller Z_ og Z2 sammen betyr et oksygen- eller svovelatom, en imino-gruppe som eventuelt er substituert med en alkyl- eller fenylalkylgruppe, hvor de ovenfor nevnte alkyldeler kan inneholde 1-3 karbonatomer, eller en alkylendioksygruppe med 2 eller 3 karbonatomer, cykliseres, eller b) en forbindelse med formel -group, where R2 is as defined above and R6 is a hydrogen atom or, if R_ constitutes a hydrogen atom, an optionally substituted by a phenyl group alkyl group with 1-3 carbon atoms, Z_ and Z 2 , which may be the same or different, mean nucleophilic leaving groups, such as optionally substituted amino, alkoxy, phenylalkyloxy, phenoxy, alkylmercapto, phenylalkylmercapto or phenylthio groups, or Z_ and Z2 together mean an oxygen or sulfur atom, an imino group which is optionally substituted with an alkyl or phenylalkyl group, where the above-mentioned alkyl parts may contain 1-3 carbon atoms, or an alkylenedioxy group with 2 or 3 carbon atoms, cyclized, or b) a compound of formula hvor R3 , R4 og R5 er som ovenfor definert, en av restene A2 eller B2 betyr enR _N H-gruppe, hvor R: er som ovenfor definert, og den andre av restene A2 eller B2 er en NH2 -gruppe, omsettes med et aldehyd med formel where R3 , R4 and R5 are defined as above, one of the residues A2 or B2 means an R_N H group, where R: is as defined above, and the other of the residues A2 or B2 is an NH2 group, is reacted with an aldehyde of formula hvor R2 er som ovenfor definert, hvorpå en således oppnådd forbindelse oksyderes, og eventuelt en således oppnådd forbindelse med formel I, hvor Rx utgjør et hydrogenatom og/ellerR2 inneholder en hydroksy-eller merkaptogruppe, ved alkylering overføres i den tilsvarende alkylforbindelse, og/eller en således oppnådd forbindelse med formel I, hvor R2 inneholder en aminogruppe, ved alkanoylering overføres i den tilsvarende alkanoylforbindelse, og/eller en således oppnådd forbindelse med formel I, hvor R2 utgjør en vinylengruppe som terminalt er substituert med en fenyl- eller pyridylgruppe, ved katalytisk hydrering overføres i en tilsvarende forbindelse med formel I, hvor R2 utgjør en etylengruppe som terminalt er substituert med en fenyl- eller pyridylgruppe, og/eller en således oppnådd forbindelse med formel I, hvor R__ utgjør en benzylgruppe, ved katalytisk hydrering overføres i en tilsvarende forbindelse med formel I, hvor R: utgjør et hydrogenatom, og/eller en således oppnådd forbindelse med formel I, hvor R2 utgjør en pyridinring, ved katalytisk hydrering overføres i en tilsvarende forbindelse med formel I, hvor R2 utgjør en piperidinylgruppe, og/eller en således oppnådd forbindelse med formel I, hvor R2 utgjør en alkoksyfenyl- eller dialkoksyfenylgruppe, ved eterspaltning overføres i en tilsvarende forbindelse med formel I, hvor R2 utgjør en hydroksyfenyl- eller dihydroksyfenylgruppe, og/eller en således oppnådd forbindelse med formel I, hvor R2 utgjør en alkylmerkaptofenyl- eller dialkylmerkaptofenylgruppe, ved oksydasjon overføres i en tilsvarende forbindelse med formel I, hvor R2 utgjør en alkylsulfinyl-, alkylsulfonyl-, dialkylsulfinyl- eller dialkylsulfonyl-fenylgruppe, og/eller, en således oppnådd forbindelse med den generelle formel I, overføres i dens syreaddisjonssalter, spesielt i fysiologisk akseptable salter med uorganiske eller organiske syrer.where R2 is defined as above, after which a compound thus obtained is oxidized, and optionally a thus obtained compound of formula I, where Rx constitutes a hydrogen atom and/or R2 contains a hydroxy or mercapto group, by alkylation is transferred in the corresponding alkyl compound, and/or a thus obtained compound of formula I, where R2 contains an amino group, by alkanoylation is transferred into the corresponding alkanoyl compound, and/or a thus obtained compound of formula I, where R2 constitutes a vinylene group which is terminally substituted with a phenyl or pyridyl group, by catalytic hydrogenation is transferred into a corresponding compound of formula I, where R2 constitutes an ethylene group which is terminally substituted with a phenyl or pyridyl group, and or a thus obtained compound of formula I, where R__ constitutes a benzyl group, by catalytic hydrogenation is transferred into a corresponding compound of formula I, where R: constitutes a hydrogen atom, and/or a thus obtained compound of formula I, where R 2 forms a pyridine ring, by catalytic hydrogenation is transferred into a corresponding compound of formula I, where R 2 forms a piperidinyl group, and/or a thus obtained compound of formula I, where R2 constitutes an alkoxyphenyl or dihydroxyphenyl group, by ether cleavage is transferred into a corresponding compound of formula I, where R2 constitutes a hydroxyphenyl or dihydroxyphenyl group, and or a thus obtained compound of formula I, where R2 constitutes an alkylmercaptophenyl or dialkylmercaptophenyl group, by oxidation is transferred into a corresponding compound of formula I, where R2 constitutes an alkylsulfinyl, alkylsulfonyl, dialkylsulfinyl or dialkylsulfonyl-phenyl group, and/or, a thus obtained compound of the general formula I is transferred in its acid addition salts, especially in physiologically acceptable salts with inorganic or organic acids. 2. Fremgangsmåte ifølge krav 1, for fremstilling av for-bindelsen 5-etyl-7,7-dimetyl-2-(4-pyridyl)-6,7-dihydro-3H,5H-pyrrolo-[2,3-f]benzimidazol-6-on, dens 3H tautomerer og dens syre-addis jonssalter , karakterisert ved at man benytter tilsvarende utgangsforbindelser.2. Process according to claim 1, for producing the compound 5-ethyl-7,7-dimethyl-2-(4-pyridyl)-6,7-dihydro-3H,5H-pyrrolo-[2,3-f] benzimidazol-6-one, its 3H tautomers and its acid addition salts, characterized by using corresponding output connections.
NO874780A 1986-11-18 1987-11-17 ANALOGUE PROCEDURE FOR THE PREPARATION OF THERAPEUTIC ACTIVE PYRROLO-BENZIMIDAZOLE DERIVATIVES. NO874780L (en)

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