HK86894A - Dialkoxyridines, process for their preparation, their application and medicaments containing them - Google Patents

Dialkoxyridines, process for their preparation, their application and medicaments containing them Download PDF

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Publication number
HK86894A
HK86894A HK86894A HK86894A HK86894A HK 86894 A HK86894 A HK 86894A HK 86894 A HK86894 A HK 86894A HK 86894 A HK86894 A HK 86894A HK 86894 A HK86894 A HK 86894A
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Hong Kong
Prior art keywords
methyl
methoxy
dimethoxy
radical
solution
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HK86894A
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German (de)
English (en)
Inventor
Bernhard Dr. Kohl
Ernst Dr. Sturm
Kurt Prof.Dr. Klemm
Richard Dr. Riedel
Volker Dr. Figala
Georg Dr. Rainer
Hartmann Dr. Schaefer
Joerg Dr. Senn-Bilfinger
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Altana Pharma Ag
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Application filed by Altana Pharma Ag filed Critical Altana Pharma Ag
Publication of HK86894A publication Critical patent/HK86894A/xx

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    • 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
    • C07D213/60—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 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
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/69—Two or more oxygen atoms
    • 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
    • C07D213/60—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 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
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/65—One oxygen atom attached in position 3 or 5
    • 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
    • C07D213/89—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 with hetero atoms directly attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles 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 in position 2
    • C07D235/26—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
    • C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
    • C07D317/52—Radicals substituted by halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
    • C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
    • C07D319/16—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D319/20—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring with substituents attached to the hetero 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
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Claims (13)

1. Procédé de préparation de dialkoxypyridines répondant à la formule générale I: dans laquelle
R1 représente un reste alkyle en C1 à C3 substitué en totalité ou en majeure partie par du fluor, ou un reste chlorodifluorométhyle, et
R1' représente un atome d'hydrogène ou d'halogène, un reste trifluorométhyle, un reste alkyle en C1 à C3 ou un reste alkoxy éventuellement substitué en totalité ou en majeure partie par du fluor, ou bien
R1 et R1' forment avec l'atome d'oxygène auquel R1 est lié un reste alkylène-dioxy en Ci ou C2 éventuellement substitué en totalité ou en partie par du fluor, ou un reste chlorotrifluoro-éthylène-dioxy,
R3 représente un reste alkoxy en C, à C3, l'un des restes R2 et R4 représente un reste alkoxy en C1 à C3 et l'autre un atome d'hydrogène ou un reste alkyle en C1 à C3, et n représente les nombres 0 ou 1, et leurs sels, caractérisé en ce que l'on fait réagir
a) des mercaptobenzimidazoles répondant à la formule générale II avec des dérivés de picoline III ou
b) des benzimidazoles répondant à la formule générale IV avec des mercaptopicolines V ou
c) des o-phénylènediamines répondant à la formule générale VI avec des dérivés de l'acide formique VIIet éventuellement, subséquemment, l'on oxyde les sulfures de 2-benzimidazolyl-2-pyridylméthyle répondant à la formule générale VIII, obtenus en a), b) ou c) et/ou on les transforme en sels, ou bien l'on fait réagir
d) des benzimidazoles répondant à la formule générale IX avec des dérivés de la pyridine X
e) des dérivés sulfinyliques répondant à la formule générale XI avec des dérivés de 2-picoline XII et éventuellement, subséquemment, l'on effectue la transformation en sels,
Y, Z, Z' et Z" représentant des croupes scindables appropriés,
M représentant un atome de métal alcalin (Li, Na ou K),
M' représentant l'équivalent d'un atome métallique, et
R1, R1', R2, R3, R4 et n ayant les significations indiquées précédemment.
2. Procédé selon la revendication 1, où
R1 représente un reste alkyle en C, à C3 substitué en totalité ou en majeure partie par du fluor, ou un reste chlorodifluorométhyle,
R1' représente un- atome d'hydrogène ou d'halogène, un reste trifluorométhyle, un reste alkyle en C1 à C3 ou un reste alkoxy en C1 à C3 éventuellement substitué en totalité ou en majeure partie par du fluor,
R3 représente un reste alkoxy en C1 à C3,
l'un des restes R2 et R4 représente un reste alkoxy en C1 à C3 et l'autre un atome d'hydrogène ou un reste alkyle en C1 à C3, et n représente les nombres 0 ou 1.
3. Procédé selon la revendication 1, où
R1 et R1' forment avec l'atome d'oxygène auquel R1 est lié un reste alkylène-dioxy en C1 ou C2, éventuellement substitué en totalité ou en partie par du fluor, ou un reste chlorotrifluoro-éthylène-dioxy,
R3 représente un reste alkoxy en C1 à C3, l'un des restes R2 et R4 représente un reste alkoxy en C1 à C3 et l'autre un atome d'hydrogène ou un reste alkyle en Ci à C3, et n représente les nombres 0 ou 1.
4. Procédé selon la revendication 1, où
R1 représente un reste 1,1,2,2-tétrafluoroéthyle, trifluorométhyle, 2,2,2-trifluoroéthyle ou difluorométhyle, R1' représente un atome d'hydrogène,
R3 représente un reste méthoxy, l'un des restes R2 ou R4 représente un reste méthoxy et l'autre un atome d'hydrogène ou un reste méthyle, et n représente les nombres 0 ou 1.
5. Procédé selon la revendication 1, où
R1 et R1' forment avec l'atome d'oxygène auquel R1 est lié un reste difluorométhylène-dioxy ou un reste méthylène-dioxy,
R3 un reste méthoxy, l'un des restes R2 ou R4 un reste méthoxy et l'autre un atome d'hydrogène ou un reste méthyle et n les nombres 0 ou 1.
6. Procédé de préparation de composés répondant à la formule générale 1 selon la revendication 1, où R1, R1', R2, R3 et R4 ont les significations indiquées dans la revendication 1 et n représente le nombre 0, caractérisé en ce qu'on fait réagir des mercapto-benzimidazoles répondant à la formule générale Il avec des dérivés de picoline III et éventuellement subséquemment, on effectue la transformation en sels d'addition acides.
7. Procédé de préparation de composés répondant à la formule générale 1 selon la revendication 1, où R1, R1', R2, R3 et R4 ont les significations indiquées dans la revendication 1 et n représente le nombre 1, caractérisé en ce qu'on oxyde les sulfures de 2-benzimidazolyl-2-pyridylméthyle répondant à la formule générale VIII et on les transforme éventuellement, subséquemment, en sels avec des bases.
8. Procédé de préparation de médicaments, caractérisé en ce qu'on mélange un composé répondant à la formule générale 1 selon la revendication 1 ou un de ses sels pharmacologiquement compatible avec un adjuvant pharmaceutique et/ou un support pharmaceutique.
9. Procédé de préparation de 5-difluorométhoxy-2-[(3,4-diméthoxy-2-pyridyl)méthylsulfinyl]-1H-benzimidazole et de ses sels, caractérisé en ce qu'on oxyde le 5-difluorométhoxy-2-[(3,4-diméthoxy-2-pyridyl)méthylthioJ-1 H-benzimidazole et subséquemment, si on le souhaite, on transforme le 5-difluorométhoxy-2-[(3,4-diméthoxy-2-pyridyl)méthylsulfinyl]-1H-benzimidazole ainsi obtenu en un sel.
10. Procédé de préparation de 5-difluorométhoxy-2-[(3,4-diméthoxy-2-pyridyl)méthylthio]-1H-benzimidazole et de ses sels, caractérisé en ce qu'on fait réagir le 5-difluorométhoxy-2-mercapto-1 H-benzimidazole avec la 2-chlorométhyl-3,4-diméthoxypyridine ou son sel et subséquemment, si on le souhaite, on transforme le 5-difluorométhoxy-2-[(3,4-diméthoxy-2-pyridyl)méthylthio]-1H-benzimidazole ainsi obtenu en un sel, ou bien l'on transforme le sel du 5-difluorométhoxy-2-[(3,4-diméthoxy-2-pyridyl)méthylthio]-1H-benzimidazole obtenu en son composé libre.
HK86894A 1984-06-16 1994-08-25 Dialkoxyridines, process for their preparation, their application and medicaments containing them HK86894A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH289984 1984-06-16
CH290184 1984-06-16

Publications (1)

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HK86894A true HK86894A (en) 1994-09-02

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US (1) US4758579A (fr)
EP (1) EP0166287B1 (fr)
AU (1) AU578703B2 (fr)
BG (1) BG61322B2 (fr)
CA (1) CA1254215A (fr)
CY (1) CY1670A (fr)
CZ (1) CZ281242B6 (fr)
DE (2) DE19475025I2 (fr)
DK (1) DK170440B1 (fr)
ES (1) ES8705875A1 (fr)
GR (1) GR851399B (fr)
HK (1) HK86894A (fr)
IE (1) IE58117B1 (fr)
IL (1) IL75400A (fr)
LU (1) LU88700I2 (fr)
MY (1) MY103021A (fr)
NL (1) NL950030I2 (fr)
NZ (1) NZ212415A (fr)
PH (2) PH21850A (fr)
PT (1) PT80641B (fr)
SG (1) SG80192G (fr)
SK (1) SK278401B6 (fr)

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CZ281242B6 (cs) 1996-07-17
NL950030I1 (fr) 1996-02-01
BG61322B2 (bg) 1997-05-30
IE58117B1 (en) 1993-07-14
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SK278401B6 (en) 1997-04-09
MY103021A (en) 1993-04-30
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PT80641A (de) 1985-07-01
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IL75400A (en) 1988-10-31
AU4364085A (en) 1985-12-19
EP0166287B1 (fr) 1989-08-23
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