DK186282A - PROCEDURE FOR PREPARING PHENYL-SUBSTITUTED PYRIDO (1,4) BENZODIAZEPINES AND INTERMEDIATES IN THE PROCEDURE - Google Patents

PROCEDURE FOR PREPARING PHENYL-SUBSTITUTED PYRIDO (1,4) BENZODIAZEPINES AND INTERMEDIATES IN THE PROCEDURE Download PDF

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Publication number
DK186282A
DK186282A DK186282A DK186282A DK186282A DK 186282 A DK186282 A DK 186282A DK 186282 A DK186282 A DK 186282A DK 186282 A DK186282 A DK 186282A DK 186282 A DK186282 A DK 186282A
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Prior art keywords
procedure
benzodiazepines
intermediates
substituted pyrido
preparing phenyl
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DK186282A
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Danish (da)
Inventor
Jr Chandler Roy Taylor
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Robins Co Inc A H
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Publication of DK186282A publication Critical patent/DK186282A/en

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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D243/00Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
    • C07D243/06Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
    • C07D243/10Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
    • C07D243/141,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D213/00Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/72Nitrogen atoms
    • C07D213/74Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/24Antidepressants
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/26Psychostimulants, e.g. nicotine, cocaine
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D471/00Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04Ortho-condensed systems

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Psychiatry (AREA)
  • Veterinary Medicine (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Pain & Pain Management (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Pyridine Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Description

Figure DK186282AD00021

II 1 12 hvor R er et hydrogenatom, en lavere alkyl, en -alk -NR R - eller en -alk^-N=CH-OC,H_-gruppe, 12 * * R og R er hver et hydrogenatom eller en lavere alkyl eller en -C(O)0-lavere alkyl-gruppe, eller R* og 2 R kan sammen med det tilstødende nitrogenatom danne en 1-phthalimido-, 1-piperidinyl-, 1-pyrrolidi-nyl-, 4-morpholino-, 1-piperazino- eller 4-substitu-eret piperazin-l-yl-heterocyclisk rest.Wherein R is a hydrogen atom, a lower alkyl, an -alk -NR R - or an -alk 2 -N = CH-OC, H-group, 12 * * R and R are each a hydrogen atom or a lower alkyl or a -C (O) O-lower alkyl group, or R * and 2 R together with the adjacent nitrogen atom may form a 1-phthalimido, 1-piperidinyl, 1-pyrrolidinyl, 4-morpholino, 1-piperazino or 4-substituted piperazin-1-yl heterocyclic residue.

Ar er en 2-, 3- eller 4-pyridinyl-, en 2- eller 3-thienyl- eller en phenyl- eller en substitueret phenyl- gruppe, idet den substituerede phenylgruppe er substitueret med 1-3 halogen-, lavere alkyl-, lavere alkoxy-, trifluormethyl- eller nitrogrupper, der kan være ens eller forskellige,Ar is a 2-, 3- or 4-pyridinyl, a 2- or 3-thienyl or a phenyl or a substituted phenyl group, the substituted phenyl group being substituted with 1-3 halogen, lower alkyl, lower alkoxy, trifluoromethyl or nitro groups which may be the same or different,

Alk^ er ligekædet eller forgrenet carbonhydrid med 1-8 carbonatimer, Z er et hydrogenatom eller et halogenatom eller en lavere alkyl-, lavere alkoxy-, hydroxy- eller nitrogruppe , Y er et hydrogenatom eller 1 eller 2 lavere alkyl-, lavere alkoxy- eller hydroxygrupper, der kan være ens eller forskellige, R og R er grupper,der kan være ens eller forskellige, og som ikke griber ind i cycliseringen af forbindelser med formlen II til forbindelser med form-3 4 len I, idet R og R hver fortrinsvis er et hydrogenatom, og X er =0 eller Q^, hvor er en gruppe eller et atom, der ikke griber ind i cycliseringen af forbindelser med formlen II til forbindelser med formlen I, og som kan fraspaltes før eller vinder cycl i seringsreaktionen til dannelse af en -C=0-gruppe eller et carbonyl-ækvivalent såsom et ketal, thioketal eller et gem-dihalogenid, som selv fås ved omsætning af en halogenaminopyrimidin med formlenAlk 2 is straight or branched hydrocarbon having 1-8 carbon atoms, Z is a hydrogen atom or a halogen atom or a lower alkyl, lower alkoxy, hydroxy or nitro group, Y is a hydrogen atom or 1 or 2 lower alkyl, lower alkoxy groups. or hydroxy groups which may be the same or different, R and R are groups which may be the same or different and which do not interfere with the cyclization of compounds of formula II to compounds of formula I, wherein R and R are each preferably is a hydrogen atom and X is = 0 or Q 2, where is a group or atom which does not interfere with the cyclization of compounds of formula II to compounds of formula I and which can be cleaved off before or win cycl in the reaction of reaction to forming a -C = O group or a carbonyl equivalent such as a ketal, thioketal or a gem dihalide, which is itself obtained by reacting a halogenaminopyrimidine of the formula

Figure DK186282AD00031

med en (aminophenyl)arylmethanon med formlenwith an (aminophenyl) arylmethanone of the formula

Figure DK186282AD00032

Såvel forbindelserne med formlen I som forbindelserne med formlen II har antidepressiv virkning.Both the compounds of formula I and the compounds of formula II have antidepressant effect.

DK186282A 1981-09-24 1982-04-26 PROCEDURE FOR PREPARING PHENYL-SUBSTITUTED PYRIDO (1,4) BENZODIAZEPINES AND INTERMEDIATES IN THE PROCEDURE DK186282A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US30508081A 1981-09-24 1981-09-24

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DK186282A true DK186282A (en) 1983-03-25

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Family Applications (3)

Application Number Title Priority Date Filing Date
DK186282A DK186282A (en) 1981-09-24 1982-04-26 PROCEDURE FOR PREPARING PHENYL-SUBSTITUTED PYRIDO (1,4) BENZODIAZEPINES AND INTERMEDIATES IN THE PROCEDURE
DK403487A DK403487A (en) 1981-09-24 1987-08-03 PROCEDURE FOR THE PREPARATION OF PHENYL-SUBSTITUTED PYRIDOOE1,4AABENZODIAZEPINES AND INTERMEDIATES OF THE PROCEDURE
DK403387A DK403387A (en) 1981-09-24 1987-08-03 PROCEDURE FOR THE PREPARATION OF PHENYL-SUBSTITUTED PYRIDOOE1,4AABENZODIAZEPINES AND INTERMEDIATES OF THE PROCEDURE

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DK403487A DK403487A (en) 1981-09-24 1987-08-03 PROCEDURE FOR THE PREPARATION OF PHENYL-SUBSTITUTED PYRIDOOE1,4AABENZODIAZEPINES AND INTERMEDIATES OF THE PROCEDURE
DK403387A DK403387A (en) 1981-09-24 1987-08-03 PROCEDURE FOR THE PREPARATION OF PHENYL-SUBSTITUTED PYRIDOOE1,4AABENZODIAZEPINES AND INTERMEDIATES OF THE PROCEDURE

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JP (1) JPS5865290A (en)
KR (1) KR890000764B1 (en)
BE (1) BE891666A (en)
CA (1) CA1199324A (en)
CH (1) CH651833A5 (en)
DE (1) DE3150522A1 (en)
DK (3) DK186282A (en)
EG (1) EG15904A (en)
ES (6) ES8303348A1 (en)
FI (1) FI71935C (en)
FR (1) FR2515183B1 (en)
GR (1) GR78473B (en)
HU (2) HU189426B (en)
IE (1) IE52493B1 (en)
IL (1) IL64284A (en)
IN (1) IN156080B (en)
IT (1) IT1146728B (en)
LU (1) LU83865A1 (en)
NL (1) NL8200549A (en)
NO (1) NO157700C (en)
NZ (1) NZ198999A (en)
PH (2) PH17847A (en)
PL (6) PL143596B1 (en)
PT (1) PT74286B (en)
SE (2) SE448629B (en)
YU (1) YU46128B (en)
ZA (1) ZA817866B (en)

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3825549A (en) * 1972-10-24 1974-07-23 Squibb & Sons Inc Certain dihydropyrido(2,1-b)(1,3)benzodi-azepines and benzodiazocines
DE2424811C3 (en) * 1974-05-22 1981-08-20 Dr. Karl Thomae Gmbh, 7950 Biberach Pyrido-benzodiazepinones, process for their preparation and medicaments containing them
SE422799B (en) * 1975-05-28 1982-03-29 Merck & Co Inc ANALOGY PROCEDURE FOR PREPARATION OF 1,3-DIHYDROIMIDAZO (4,5-B) PYRIDIN-2-ONER

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Publication number Publication date
KR890000764B1 (en) 1989-04-05
ES8308563A1 (en) 1983-09-16
DK403487D0 (en) 1987-08-03
PL234426A1 (en) 1984-01-02
DK403387D0 (en) 1987-08-03
GR78473B (en) 1984-09-27
BE891666A (en) 1982-04-16
PL241409A1 (en) 1984-05-21
PL139381B1 (en) 1987-01-31
FR2515183A1 (en) 1983-04-29
IL64284A0 (en) 1982-02-28
FR2515183B1 (en) 1986-11-14
IT8168605A0 (en) 1981-12-09
HUT34732A (en) 1985-04-28
FI71935C (en) 1987-03-09
HU187393B (en) 1985-12-28
IE52493B1 (en) 1987-11-25
NO157700C (en) 1988-05-04
ZA817866B (en) 1982-10-27
SE8600688D0 (en) 1986-02-17
NO157700B (en) 1988-01-25
ES516051A0 (en) 1983-09-16
YU62582A (en) 1986-04-30
SE8600688L (en) 1986-02-17
PL143597B1 (en) 1988-02-29
PL143322B1 (en) 1988-02-29
PT74286A (en) 1982-02-01
ES507971A0 (en) 1983-02-01
ES8607726A1 (en) 1986-06-01
HU189426B (en) 1986-07-28
PL241410A1 (en) 1984-01-02
PL138859B1 (en) 1986-11-29
IE812769L (en) 1983-03-24
SE455305B (en) 1988-07-04
SE448629B (en) 1987-03-09
EG15904A (en) 1987-03-30
PL143596B1 (en) 1988-02-29
ES543328A0 (en) 1986-06-01
YU46128B (en) 1993-05-28
ES526563A0 (en) 1986-02-01
IT1146728B (en) 1986-11-19
ES8504148A1 (en) 1985-04-01
SE8106573L (en) 1983-03-25
CH651833A5 (en) 1985-10-15
PH17847A (en) 1985-01-09
LU83865A1 (en) 1983-09-02
NZ198999A (en) 1987-07-31
FI813976L (en) 1983-03-25
DK403487A (en) 1987-08-03
PH20536A (en) 1987-02-09
JPS5865290A (en) 1983-04-18
IL64284A (en) 1986-12-31
CA1199324A (en) 1986-01-14
NO813839L (en) 1983-03-25
DK403387A (en) 1987-08-03
DE3150522A1 (en) 1983-04-07
PT74286B (en) 1983-06-27
PL137068B1 (en) 1986-04-30
FI71935B (en) 1986-11-28
ES8303348A1 (en) 1983-02-01
ES8604531A1 (en) 1986-02-01
ES516052A0 (en) 1984-01-16
ES526562A0 (en) 1985-04-01
ES8402295A1 (en) 1984-01-16
KR830009058A (en) 1983-12-17
IN156080B (en) 1985-05-11
NL8200549A (en) 1983-04-18

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