HK181396A - Piperazinyl-and piperidinyl-cyclohexanols - Google Patents

Piperazinyl-and piperidinyl-cyclohexanols Download PDF

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HK181396A
HK181396A HK181396A HK181396A HK181396A HK 181396 A HK181396 A HK 181396A HK 181396 A HK181396 A HK 181396A HK 181396 A HK181396 A HK 181396A HK 181396 A HK181396 A HK 181396A
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cyclohexanol
piperazinyl
methyl
benzodioxol
compound
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HK181396A
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French (fr)
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Ronald J. Mattson
John D. Catt
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Bristol-Myers Squibb Company
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    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
    • C07D295/096—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
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    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
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    • C07C45/59—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom in five-membered rings
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    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/703—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups
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    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
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    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/10—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
    • C07D211/14—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
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    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
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    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
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    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
    • C07D211/22—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
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    • 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
    • C07D317/54—Radicals substituted by oxygen atoms
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    • 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
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    • 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
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    • C07D405/08—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 linked by a carbon chain containing alicyclic rings
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    • C07C2601/14—The ring being saturated

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Claims (12)

  1. Verbindung der Formel I oder ein pharmazeutisch verträgliches Salz davon: worin R₁ und R₂ unabhängig voneinander ausgewählt sind unter H, Halogen, CF₃ oder C₁₋₄-Alkoxygruppen, wobei jedoch R₁ und R₂ nicht gleichzeitig für H stehen können und R₁ und R₂, wenn sie auf benachbarten Kohlenstoffatomen angeordnet sind, zusammen eine -Brücke bilden, worin n für eine ganze Zahl von 1 bis 3 steht; R₃ für H oder C₁₋₄-Alkyl steht; R₄ und R₅ unabhängig voneinander ausgewählt sind unter H, C₁₋₄-Alkyl oder -Phenyl; Y für N oder CH steht; und Ar für 3-Pyridinyl, 4-Pyridinyl, 2-Thienyl, 2-Furanyl, 1-Methyl-2-pyrrolyl, einen unsubstituierten Phenylring oder einen substituierten Phenylring der Strukturformel II steht: worin X und X' für Halogen, Nitro, Amino, Carboxamid, C₁₋₄-Alkyl, C₁₋₄-Alkoxy, C₁₋₄-Haloalkyl, C₁₋₄-Alkylthio stehen oder X und X' zusammen eine -Brücke (n = 1-3) bilden können; p und q für eine Zahl von 0 bis 5 stehen können, wobei p + q ≦ 5 ist.
  2. Verbindung nach Anspruch 1, worin R₁ und R₂ zusammen die Brücke (n = 1-3) bilden.
  3. Verbindung nach Anspruch 2, worin R₃, R₄ und R₅ jeweils für H stehen.
  4. Verbindung nach Anspruch 3, worin Y für CH steht.
  5. Verbindungen nach Anspruch 4, die ausgewählt sind unter Z-1-(1,3-Benzodioxol-5-yl)-4-[4-(phenylmethyl)-1-piperidinyl]-cyclohexanol; Z-1-(4-Methoxyphenyl)-4-[4-(phenylmethyl)-1-piperidinyl]-cyclohexanol; Z-1-(4-Fluorphenyl)-4-[(2,5-difluorphenyl)methyl]-1-piperidinyl]-cyclohexanol; Z-1-[4-(1,3-Benzodioxol-5-yl)-4-methoxy-1-cyclohexyl]4-[3-methoxyphenyl)methyl]piperidin; Z-1-(4-Fluorphenyl)-4-[4-(phenylmethyl)-1-piperidinyl]-cyclohexanol; Z-1-(4-Fluorphenyl)-4-[4-(3-methoxyphenyl)methyl]-1-piperidinyl]cyclohexanol; Z-1-(1,3-Benzodioxol-5-yl)-4-[4-[(2,5-difluorphenyl)methyl]-1-piperidinyl]cyclohexanol; Z-1-(1,4-Benzodioxan-6-yl)-4-[4-[(3-methoxyphenyl)methyl]-1-piperidinyl]cyclohexanol; Z-1-[4-(1,4-Benzodioxan-6-yl)-4-methoxy-1-cyclohexyl]-4-[3-(methoxyphenyl)methyl]piperidinfumarat; Z-1-[4-(1,3-Benzodioxol-5-yl)-4-methoxy-1-cyclohexyl]-4-[(2,5-difluorphenyl)methyl]piperidinfumarat.
  6. Verbindungen nach Anspruch 3, worin Y für N steht.
  7. Verbindung nach Anspruch 6, die ausgewählt ist unter Z-1-(4-Fluorphenyl)-4-[4-(2,5-difluorphenyl)methyl]-1-piperazinyl]cyclohexanol; Z-1-(1,3-Benzodioxol-5-yl)-4-[4-[(2-fluor-5-methoxyphenyl)methyl]-1-piperazinyl]cyclohexanol; Z-1-(4-Fluorphenyl)-4-[4-[(2-fluor-5-methoxyphenyl)methyl]-1-piperazinyl]cyclohexanol; Z-1-(1,3-Benzodioxol-5-yl)-4-[4-(phenylmethyl)-1-piperazinyl)cyclohexanol; Z-1-(4-Methoxyphenyl)-4-[4-(phenylmethyl)-1-piperazinyl]cyclohexanol; Z-1-[4-(1,3-Benzodioxol-5-yl)-4-methoxycyclohexyl]-4-(phenylmethyl)piperazin; Z-1-(1,4-Benzodioxan-6-yl)-4-[4-(phenylmethyl)-1-piperazinyl]cyclohexanol; Z-1-(1,3-Benzodioxol-5-yl)-4-[4-[(3-methoxyphenyl)methyl]-1-piperazinyl]cyclohexanol; Z-1-(1,3-Benzodioxol-5-yl)-4-[4-[(3-fluorphenyl)methyl]-1-piperazinyl]cyclohexanol; Z-1-(1,3-Benzodioxol-5-yl)-4-[4-[(2-fluorphenyl)methyl]-1-piperazinyl]cyclohexanol; Z-1-(1,3-Benzodioxol-5-yl)-4-[4-[(2-methylphenyl)methyl]-1-piperazinyl]cyclohexanol; Z-1-(1,3-Benzodioxol-5-yl)-4-[4-[(2-nitrophenyl)methyl]-1-piperazinyl]cyclohexanol; Z-1-(1,3-Benzodioxol-5-yl)-4-[4-[(2-chlorphenyl)methyl]-1-piperazinyl]cyclohexanol; Z-1-(1,3-Benzodioxol-5-yl)-4-[4-[(2,5-dichlorphenyl)methyl]-1-piperazinyl]cyclohexanol; Z-1-(1,3-Benzodioxol-5-yl)-4-[4-[(2,5-difluorphenyl)methyl]-1-piperazinyl]cyclohexanol; Z-1-(1,3-Benzodioxol-5-yl)-4-[4-[(2-bromphenyl)methyl]-1-piperazinyl]cyclohexanol; Z-1-(1,3-Benzodioxol-5-yl)-4-[4-[(2,3-difluorphenyl)methyl]-1-piperazinyl]cyclohexanol; Z-1-(1,3-Benzodioxol-5-yl)-4-[4-[(3,5-difluorphenyl)methyl]-1-piperazinyl]cyclohexanol; Z-1-(1,3-Benzodioxol-5-yl)-4-[4-[(2-iodphenyl)methyl]-1-piperazinyl]cyclohexanol; Z-1-(1,3-Benzodioxol-5-yl)-4-[4-[(1,3-benzodioxo-4-yl)methyl]-1-piperazinyl]cyclohexanol; Z-1-(1,3-Benzodioxol-5-yl)-4-[4-(diphenylmethyl)-1-piperazinyl]cyclohexanol; Z-1-(1,3-Benzodioxol-5-yl)-4-[4-(1-phenylethyl)-1-piperazinyl]cyclohexanol; Z-1-(4-Fluorphenyl)-4-[4-[(3-methoxyphenyl)methyl]-1-piperazinyl]cyclohexanol; Z-1-(4-Fluorphenyl)-4-[4-[(2-chlorphenyl)methyl]-1-piperazinyl]cyclohexanol; Z-1-[4-(4-Fluorphenyl)-4-methoxy-1-cyclohexyl]-4-[(3-methoxyphenyl)methyl]piperazin; Z-1-(1,3-Benzodioxol-5-yl)-4-[4-(2-thienylmethyl)-1-piperazinyl]cyclohexanol.
  8. Pharmazeutische Zusammensetzung, umfassend wenigstens eine Verbindung nach einem der Ansprüche 1 bis 7 und einen pharmazeutisch akzeptablen Träger.
  9. Verwendung wenigstens einer Verbindung nach einem der Ansprüche 1 bis 7 zur Herstellung einer pharmazeutischen Zusammensetzung zur Behandlung von Angstzuständen.
  10. Verwendung wenigstens einer Verbindung nach einem der Ansprüche 1 bis 7 zur Herstellung einer pharmazeutischen Zusammensetzung zur prophylaktischen Behandlung von Migräne.
  11. Verfahren zur Herstellung der Verbindungen der Formel I nach einem der Ansprüche 1 bis 7, wobei man eine Verbindung der Formel worin R₄ und R₅ für Wasserstoff stehen und Ar und Y wie in Anspruch 1 definiert sind, mit worin X für MgBr oder Li steht und R₁ und R₂ wie in Anspruch 1 definiert sind, zu einer Verbindung der Formel I umsetzt, worin R₃, R₄ und R₅ für Wasserstoff stehen, oder eine Verbindung der Formel worin R₁ und R₂ wie in Anspruch 1 definiert sind, mit ArCH₂X, worin Ar wie in Anspruch 1 definiert ist und X für Halogen, p-Toluolsulfonat oder Methansulfonat steht, alkyliert oder die obige Verbindung mit einem Arylaldehyd reduktiv alkyliert, um eine Verbindung der Formel I, worin Y für N steht und R₃, R₄ und R₅ für Wasserstoff stehen, zu erhalten, und gegebenenfalls die erhaltene Verbindung mit einem Alkylierungsmittel und einer geeigneten Base in einem geeigneten Lösungsmittel alkyliert, um eine entsprechende Verbindung der Formel I, worin R₃ für C₁₋₄-Alkyl steht, zu erhalten.
  12. Verfahren zur Herstellung der Zusammensetzung nach Anspruch 8, wobei man die Verbindung mit dem Träger vermischt.
HK181396A 1991-12-13 1996-09-26 Piperazinyl-and piperidinyl-cyclohexanols HK181396A (en)

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US5977110A (en) * 1995-09-22 1999-11-02 Warner-Lambert Company Substituted cyclohexylamines as central nervous systems agents
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US5478828A (en) 1995-12-26
GR3020239T3 (en) 1996-09-30
KR100251667B1 (ko) 2000-07-01
JPH0680634A (ja) 1994-03-22
RU2088574C1 (ru) 1997-08-27
IL103875A (en) 1996-08-04
EP0546583A1 (de) 1993-06-16
US5387593A (en) 1995-02-07
CA2083913A1 (en) 1993-06-14
CY1943A (en) 1997-05-16
EP0546583B1 (de) 1996-05-22
ES2088076T3 (es) 1996-08-01
EG19999A (en) 1997-01-30
DE69210967T2 (de) 1997-01-30
ZA929008B (en) 1993-05-21
AU2981792A (en) 1993-06-17
FI925595A0 (fi) 1992-12-09
HUT67144A (en) 1995-02-28
CZ290056B6 (cs) 2002-05-15
TW234120B (de) 1994-11-11
JP3197963B2 (ja) 2001-08-13
FI925595A7 (fi) 1993-06-14
NO924802D0 (no) 1992-12-11
FI925595L (fi) 1993-06-14
MY110162A (en) 1998-02-28
DE69210967D1 (de) 1996-06-27
HU215963B (hu) 1999-03-29
CZ362092A3 (en) 1993-12-15
DK0546583T3 (da) 1996-07-01
MX9207074A (es) 1993-07-01
HU9203948D0 (en) 1993-04-28
NO301326B1 (no) 1997-10-13
AU661525B2 (en) 1995-07-27
IL103875A0 (en) 1993-04-04
NO924802L (no) 1993-06-14
CA2083913C (en) 2000-11-07
ATE138367T1 (de) 1996-06-15

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