FI68049C - Foerfarande foer framstaellning av farmakologiskt verksamma 2-cyl-aminometyl-1,4-bensodiazepinfoereningar samt vid dera s ramstaellning anvaendbara mellanprodukter - Google Patents

Foerfarande foer framstaellning av farmakologiskt verksamma 2-cyl-aminometyl-1,4-bensodiazepinfoereningar samt vid dera s ramstaellning anvaendbara mellanprodukter Download PDF

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FI68049C
FI68049C FI822148A FI822148A FI68049C FI 68049 C FI68049 C FI 68049C FI 822148 A FI822148 A FI 822148A FI 822148 A FI822148 A FI 822148A FI 68049 C FI68049 C FI 68049C
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hydrogen
compounds
lower alkyl
dihydro
group
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FI822148A
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Finnish (fi)
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FI68049B (fi
FI822148A0 (fi
FI822148L (fi
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Horst Zeugner
Werner Benson
Hans Liepmann
Wolfgang Milkowski
Dietmar Roemer
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Kali Chemie Pharma Gmbh
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/04—Centrally acting analgesics, e.g. opioids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic 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
    • C07D213/02—Heterocyclic 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
    • C07D213/04—Heterocyclic 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
    • C07D213/24—Heterocyclic 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 substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
    • C07D213/46—Oxygen atoms
    • C07D213/50—Ketonic radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D267/00—Heterocyclic compounds containing rings of more than six members having one nitrogen atom and one oxygen atom as the only ring hetero atoms
    • C07D267/02—Seven-membered rings
    • C07D267/08—Seven-membered rings having the hetero atoms in positions 1 and 4
    • C07D267/12—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
    • C07D267/14—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings

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

Claims (5)

1. Förfarande för framställning av farmakologiskt verksam 2-acylaminometyl-lH-2,3-d ihydro-1,4-bensod iazepin-fören ing enligt formeln I samt dess optiska isomerer och syraadditions-salter isCH2-N-C-(CH2)nR3 "6 H i vilken formel är väte eller lägre alkyl R2 är väte, n är 0, 1 eller 2, R3 är nägon av följande grupper a, b, c eller d J R12 «8 abc <1 där X är kväve eller svavel, R7 är väte, lägre alkyl eller halogen, Rg är väte eller lägre alkyl, R9 är väte, RlO är väte eller klor, Rl1 är väte, lägre alkyl, lägre alkoxi, hydroxi, halogen, nitro, trifluormetyl, cyano, amino, lägre mono- eller dialkyl-amino, lägre monoalkanoylamino, eller lägre alkanoyloxi, r12 är väte, lägre alkyl, lägre alkoxi, halogen, hydroxi eller lägre alkanoyloxi, eller 56 68049 Rll och R^2 är bundna. vid bredvid varandra liggande kolatomer och bildar tillsaminans en metylendioxigrupp, R4 är nägon av de ovan angivna grupperna a, b eller c, R5 är väte, lägre alkyl, lägre alkoxi, halogen eller nitro, och Rg är väte, lägre alkyl, lägre alkoxi eller halogen, eller R5 och Rg är bundna . vid bredvid varandra liggande kolatomer och bildar tillsammans en metylendioxigrupp, kännetecknat därav att en 2-aminometyl-lH-2,3-dihydro-l,4-bensodiazepin förening enligt formeln II C!!2-IIH 'pp - i vilken formel R^, R2, R4, R5 och Rg är samma som ovan acyleras med en syra eller ett syraderivat enligt formeln III R3-(CH2)n-CO-Y III i vilken formel R3 och n är samma som ovan och Y är en hydroxigrupp eller en aminolytiskt avspaltbar grupp och man eventuellt i föreningar enligt den allmänna formeln I, där R5, R^i och/eller R^2 är lägre alkanoyloxi- eller alkanoyl-aminogrupper, hydrolyserar dessa grupper tili fr ia hydroxi-eller aminogrupper, och eventuellt separerar de racemiska blandningarna av föreningar med formeln I i sinä optiskt aktiva isomerer, och eventuellt omvandlar föreningarna enliggt formeln I tili sinä syraadditionssalter eller omvandlar syra-additionssalter tili fr ia föreningar enligt formeln I. 57 6 8049
2. Förfarande enligt patentkravet 1 för framställning av 2-acylaminometyl-lH-2,3-dihydro-1,4-bensodiazepinföreningar, kännetecknat av att R3, R2r R4, R5/ ^6 och n är samma som ovan angivits R3 är gruppen a, där X är samma som ovan angivits och R7 är väte, lägre alkyl eller dä X är svavel kan R7 vara även fluor, klor eller brom, eller R3 är gruppen b, där Rg och Rg samma som ovan angivits eller R3 är gruppen cf där R^q är väte, eller R3 är gruppen d, där R^ är väte, lägre alkyl, lägre alkoxi, halogen eller cyano och R32 är väte, lägre alkyl, lägre alkoxi eller halogen eller R-j^ och R^ är bundna vid bredvid varandra liggande kolatomer och hildar tillsammans en metylendioxigrupp.
3. Förfarande för framställning av 1-metyl-2-((4-cyanobenso-yl) -aminometvl) -5- (3 '-tiofen) -1H-2,3-d ihydro-1,4-bensod iazepinföreningar medelst förfarandet enligt patentkravet 1.
4. 2-aminometyl-lH-2,3-d ihydro-1,4-bensod iazepinföreningar enligt den allmänna formeln Ha fl li j R1 IIa *V i vilken formel R3 är väte eller lägre alkyl R2 är väte R4' är näqon av följande grupper a', b eller c. 58 68049 -0-«7 "O-'" k a· b c i vilka formler R7 är väte, lägre alkyl eller haloqen, Rg är väte eller lägre alkvl, Rg är väte, R^q är väte eller klor, R5 är väte, lägre alkyl, lägre alkoxi, halogen eller nitro, och Rg är väte, lägre alkyl, lägre alkoxi eller halogen eller R5 och Rg är bundna vid bredvid varandra liggande kolatomer och bildar tillsammans en metvlendioxigrupp, samt deras optiska isomerer och deras syraadditionssalter.
5. 2-azidometyl-lH-2, 3-dihydro-l ,4-bensod iät sepin för en ingar enligt formeln IV ?i l>“Λ Rs"pO M i vilken formel R^ är väte eller lägre alkyl R4 är en grupp enligt nägon av följande formler
FI822148A 1981-06-19 1982-06-15 Foerfarande foer framstaellning av farmakologiskt verksamma 2-cyl-aminometyl-1,4-bensodiazepinfoereningar samt vid dera s ramstaellning anvaendbara mellanprodukter FI68049C (fi)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19813124013 DE3124013A1 (de) 1981-06-19 1981-06-19 2-acylaminomethyl-1,4-benzodiazepin-verbindungen sowie verfahren und zwischenprodukte zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
DE3124013 1981-06-19

Publications (4)

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FI822148A0 FI822148A0 (fi) 1982-06-15
FI822148L FI822148L (fi) 1982-12-20
FI68049B FI68049B (fi) 1985-03-29
FI68049C true FI68049C (fi) 1985-07-10

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FI822148A FI68049C (fi) 1981-06-19 1982-06-15 Foerfarande foer framstaellning av farmakologiskt verksamma 2-cyl-aminometyl-1,4-bensodiazepinfoereningar samt vid dera s ramstaellning anvaendbara mellanprodukter

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US (2) US4497740A (sv)
EP (1) EP0068240B1 (sv)
JP (1) JPS58968A (sv)
AT (1) ATE15802T1 (sv)
AU (1) AU547857B2 (sv)
CA (1) CA1188299A (sv)
DD (1) DD202553A5 (sv)
DE (2) DE3124013A1 (sv)
DK (1) DK274082A (sv)
ES (1) ES8304564A1 (sv)
FI (1) FI68049C (sv)
GR (1) GR76499B (sv)
HU (1) HU188178B (sv)
IE (1) IE53464B1 (sv)
IL (1) IL66076A (sv)
NO (1) NO157420C (sv)
NZ (1) NZ201007A (sv)
PH (1) PH17911A (sv)
PT (1) PT74971B (sv)
SU (1) SU1245259A3 (sv)
ZA (1) ZA823780B (sv)

Families Citing this family (5)

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Publication number Priority date Publication date Assignee Title
US4724237A (en) * 1984-06-26 1988-02-09 Merck & Co., Inc. 2-substituted-aminomethyl-1,4-benzodiazepines
US4899425A (en) * 1986-11-14 1990-02-13 Mahlo Gmbh & Co. Kg. Apparatus for straightening weft yarns in fabrics
US6458784B1 (en) 1994-06-29 2002-10-01 Smithkline Beecham Corporation Vitronectin receptor antagonists
US5977101A (en) * 1995-06-29 1999-11-02 Smithkline Beecham Corporation Benzimidazoles/Imidazoles Linked to a Fibrinogen Receptor Antagonist Template Having Vitronectin Receptor Antagonist Activity
RU2528049C2 (ru) * 2009-09-18 2014-09-10 Мицубиси Гэс Кемикал Компани, Инк. Способ получения циклогексилалкилкетонов

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US28315A (en) * 1860-05-15 Improvement in method of decomposing fats into fatty acids and glycerine
NL131733C (sv) * 1961-06-20
USRE28315E (en) 1964-06-15 1975-01-21 Cooc.hi
US3560482A (en) * 1967-12-08 1971-02-02 Sumitomo Chemical Co Method for producing benzodiazepine derivatives
US3546212A (en) * 1968-06-12 1970-12-08 Hoffmann La Roche Oxidation of benzodiazepines with ruthenium tetroxide
US3773765A (en) * 1971-08-18 1973-11-20 Upjohn Co S-triazino(1,2-a)(1,4)benzodiazepine-1,3-(2h,4h and 2h,5h)diones
US3847935A (en) * 1972-04-12 1974-11-12 Upjohn Co 5-substituted 1-(3h,1,4-benzodiazepin-2-yl)-2-imidazolidinones
US4244869A (en) * 1972-05-03 1981-01-13 Kali-Chemie A.G. Benzodiazepine derivatives and process of making them
DE2221558C2 (de) * 1972-05-03 1982-12-02 Kali-Chemie Ag, 3000 Hannover 5-Phenyl-2,3-dihydro-1H-1,4-benzodiazepine und ihre Säureadditionssalze, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Arzneimittel
DE2314993A1 (de) * 1973-03-26 1974-10-03 Kali Chemie Pharma Gmbh Neue benzodiazepinderivate und verfahren zu deren herstellung
DE2353187A1 (de) * 1973-05-02 1974-11-14 Kali Chemie Ag Neue benzodiazepinderivate
DE2353160C2 (de) * 1973-05-02 1986-07-17 Kali-Chemie Ag, 3000 Hannover 5-Phenyl-2,3-dihydro-1H-1,4-benzodiazepine, ihre Säureadditionssalze und diese Verbindungen enthaltende Arzneimittel
DE2353165C2 (de) * 1973-05-03 1983-06-09 Kali-Chemie Ag, 3000 Hannover 1-Methyl-3-hydroxy-6-(2-chlorphenyl)-1,2,3,4-tetrahydro-1,5-benzodiazocinderivate
US3925358A (en) * 1973-07-27 1975-12-09 Hoffmann La Roche 1-Lower alkyl-2-substituted-1,4-benzodiazepines
US4368159A (en) * 1978-05-15 1983-01-11 Hoffmann-La Roche Inc. Intermediates to produce imidazodiazepines
DE2952279A1 (de) * 1979-12-24 1981-06-25 Kali-Chemie Pharma Gmbh, 3000 Hannover Neue 2-acylaminomethyl-1,4-benzodiazepine und deren salze sowie verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
HU186760B (en) * 1981-03-12 1985-09-30 Gyogyszerkutato Intezet Process for preparing 3,4-dihydro-5h-2,3-aenzodiazepine derivatives

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Publication number Publication date
JPS58968A (ja) 1983-01-06
EP0068240A1 (de) 1983-01-05
AU8499182A (en) 1982-12-23
NO157420B (no) 1987-12-07
NO157420C (no) 1988-03-16
ZA823780B (en) 1983-03-30
DK274082A (da) 1982-12-20
US4497740A (en) 1985-02-05
FI68049B (fi) 1985-03-29
ES512844A0 (es) 1983-03-01
FI822148A0 (fi) 1982-06-15
NO822037L (no) 1982-12-20
FI822148L (fi) 1982-12-20
AU547857B2 (en) 1985-11-07
DE3266521D1 (en) 1985-10-31
IL66076A0 (en) 1982-09-30
HU188178B (en) 1986-03-28
PH17911A (en) 1985-01-25
SU1245259A3 (ru) 1986-07-15
DE3124013A1 (de) 1982-12-30
GR76499B (sv) 1984-08-10
CA1188299A (en) 1985-06-04
EP0068240B1 (de) 1985-09-25
IE821468L (en) 1982-12-19
ATE15802T1 (de) 1985-10-15
DD202553A5 (de) 1983-09-21
PT74971A (en) 1982-06-01
US4649137A (en) 1987-03-10
JPH0433795B2 (sv) 1992-06-04
IE53464B1 (en) 1988-11-23
PT74971B (en) 1983-12-29
IL66076A (en) 1986-03-31
NZ201007A (en) 1985-05-31
ES8304564A1 (es) 1983-03-01

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