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HK1111681A1 - Heterocyclic compounds suitable for treating disorders that respond to modulation of the dopamine d3 receptor - Google Patents

Heterocyclic compounds suitable for treating disorders that respond to modulation of the dopamine d3 receptor Download PDF

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Publication number
HK1111681A1
HK1111681A1 HK08100350.6A HK08100350A HK1111681A1 HK 1111681 A1 HK1111681 A1 HK 1111681A1 HK 08100350 A HK08100350 A HK 08100350A HK 1111681 A1 HK1111681 A1 HK 1111681A1
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HK
Hong Kong
Prior art keywords
phenyl
methyl
alkyl
propyl
fluorinated
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HK08100350.6A
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English (en)
French (fr)
Chinese (zh)
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HK1111681B (en
Inventor
Karla Drescher
Andreas Haupt
Liliane Unger
Sean C. Turner
Wilfried Braje
Roland Grandel
Christophe Henry
Gisela Backfisch
Armin Beyerbach
Wilfried Lubisch
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AbbVie Deutschland GmbH & Co. KG
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Publication of HK1111681A1 publication Critical patent/HK1111681A1/en
Publication of HK1111681B publication Critical patent/HK1111681B/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • 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
    • C07D211/26—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 nitrogen atoms
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    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/397—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having four-membered rings, e.g. azetidine
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    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
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    • A—HUMAN NECESSITIES
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    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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    • A—HUMAN NECESSITIES
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    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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    • C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
    • C07D205/04—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
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    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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
    • C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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 radicals, substituted by hetero atoms, attached to ring carbon atoms
    • C07D207/09—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
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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
    • C07D211/26—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 nitrogen atoms
    • C07D211/28—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 nitrogen atoms to which a second hetero atom is attached
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    • 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
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    • 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
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    • 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
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    • 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
    • C07D405/12—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 chain containing hetero atoms as chain links
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Claims (22)

  1. Verbindung der Formel (I) worin
    n für 0, 1 oder 2 steht;
    G für CH2 oder CHR3 steht;
    R1 für H, C1-C6-Alkyl, C1-C6-Alkyl, das durch C3-C6-Cycloalkyl substituiert ist, C1-C6-Hydroxyalkyl, fluoriertes C1-C6-Alkyl, C3-C6-Cycloalkyl, fluoriertes C3- C6-Cycloalkyl, C3-C6-Alkenyl, fluoriertes C3-C6-Alkenyl, Formyl, Acetyl oder Propionyl steht;
    R2, R3 und R4 unabhängig voneinander für H, Methyl, Fluormethyl, Difluormethyl, oder Trifluormethyl stehen;
    A für 1,4-Phenylen, 1,2-Phenylen, 2,5-Pyridylen, 3,6-Pyridylen oder 2,5- Pyrimidylen steht und durch eine oder mehrere, unter Halogen, Methyl, Me- thoxy und CF3 ausgewählte Substituenten substituiert sein kann;
    E für NR5 steht, worin R5 für H oder C1-C3-Alkyl steht;
    Ar für einen cyclischen Rest steht, der ausgewählt ist unter Phenyl, einem 5- oder 6-gliedrigen heteroaromatischen Rest, enthaltend als Ringglieder 1, 2 oder 3 unter N, O und S ausgewählte Heteroatome, und einem Phenylring, der an einen gesättigten oder ungesättigten 5- oder 6-gliedrigen carbocycli- schen oder heterocyclischen Ring anneliert ist, wobei der heterocyclische Ring als Ringglieder 1, 2 oder 3 unter N, O und S ausgewählte Heteroato- me und/oder 1, 2 oder 3 jeweils unabhängig voneinander unter NR8 aus- gewählte heteroatomhaltige Gruppen enthält, wobei R8 für H, C1-C4-Alkyl, fluoriertes C1-C4-Alkyl, C1-C4-Alkylcarbonyl oder fluoriertes C1-C4-Alkyl- carbonyl steht, und wobei der cyclische Rest Ar 1, 2 oder 3 Substituenten Ra aufweisen kann;
    Ra für Halogen, C1-C6-Alkyl, fluoriertes C1-C6-Alkyl, C1-C6-Hydroxyalkyl, C1-C6- Alkoxy-C1-C6-alkyl, C2-C6-Alkenyl, fluoriertes C2-C6-Alkenyl, C3-C6- Cycloalkyl, fluoriertes C3-C6-Cycloalkyl, C1-C6-Alkoxy, C1-C6- Hydroxyalkoxy, C1-C6-Alkoxy-C1-C6-alkoxy, fluoriertes C1-C6-Alkoxy, C1-C6- Alkylthio, fluoriertes C1-C6-Alkylthio, C1-C6-Alkylsulfinyl, fluoriertes C1-C6- Alkylsulfinyl, C1-C6-Alkylsulfonyl, fluoriertes C1-C6-Alkylsulfonyl, Phenylsul- fonyl, Benzyloxy, Phenoxy, wobei der Phenylrest in den 3 letztgenannten Resten unsubstituiert sein oder 1 bis 3 Substituenten, ausgewählt unter C1- C4-Alkyl, fluoriertem C1-C4-Alkyl und Halogen aufweisen kann, CN, Nitro, C1-C6-Alkylcarbonyl, fluoriertes C1-C6-Alkylcarbonyl, C1-C6-Alkylcarbonyl- amino, fluoriertes C1-C6-Alkylcarbonylamino, Carboxy, NH-C(O)-NR6R7, NR6R7, NR6R7-C1-C6-Alkylen, O-NR6R7, wobei R6 und R7 jeweils unabhän- gig voneinander für H, C1-C4-Alkyl, fluoriertes C1-C4-Alkyl oder C1-C4- Alkoxy stehen oder zusammen mit N einen 4-, 5- oder 6-gliedrigen gesät- tigten oder ungesättigten Ring bilden können, oder für einen gesättigten oder ungesättigten 3- bis 7-gliedrigen heterocyclischen Ring steht, enthal- tend als Ringglieder 1, 2, 3 oder 4 unter N, O und S ausgewählte Hetero- atome und/oder 1, 2 oder 3 heteroatomhaltige Gruppen, ausgewählt unter NR9, wobei R9 eine der für R8 angegebenen Bedeutungen aufweist, SO, SO2 und CO, und wobei der heterocyclische Ring 1, 2 oder 3 Substituen- ten, ausgewählt unter Hydroxy, Halogen, C1-C6-Alkyl, fluoriertem C1-C6- Alkyl und C1-C6-Alkoxy, aufweisen kann;
    und die physiologisch verträglichen Säureadditionssalze davon.
  2. Verbindung nach Anspruch 1, worin
    R1 für H, C1-C6-Alkyl, das durch C3-C6-Cycloalkyl substituiert sein kann, fluori- ertes C1-C6-Alkyl, C3-C6-Cycloalkyl, fluoriertes C3-C6-Cycloalkyl, C3-C6- Alkenyl, fluoriertes C3-C6-Alkenyl, Formyl, Acetyl oder Propionyl steht; und
    Ar für einen cyclischen Rest steht, der ausgewählt ist unter Phenyl, einem 5- oder 6-gliedrigen heteroaromatischen Rest, enthaltend als Ringglieder 1, 2 oder 3 unter N, O und S ausgewählte Heteroatome, und einem Phenylring, der an einen gesättigten oder ungesättigten 5- oder 6-gliedrigen carbocycli- schen oder heterocyclischen Ring anneliert ist, wobei der heterocyclische Ring als Ringglieder 1, 2 oder 3 unter N, O und S ausgewählte Heteroato- me enthält, und wobei der cyclische Rest 1, 2 oder 3 Substituenten Ra auf- weisen kann, die ausgewählt sind unter Halogen, C1-C6-Alkyl, fluoriertem C1-C6-Alkyl, C3-C6-Cycloalkyl, fluoriertem C3-C6-Cycloalkyl, C1-C6-Alkoxy, fluoriertem C1-C6-Alkoxy, CN, Acetyl, Carboxy, NR6R7, NR6R7-C1-C6- Alkylen, wobei R6 und R7 jeweils unabhängig voneinander für H, C1-C4- Alkyl oder fluoriertes C1-C4-Alkyl stehen oder zusammen mit N einen 4-, 5- oder 6-gliedrigen gesättigten oder ungesättigten Ring bilden können, und einem gesättigten oder ungesättigten 5- oder 6-gliedrigen heterocyclischen Ring, enthaltend als Ringglieder 1, 2 oder 3 unter N, O und S ausgewählte Heteroatome.
  3. Verbindung nach einem der Ansprüche 1 oder 2, worin n für 0 oder 1 steht.
  4. Verbindung nach einem der vorhergehenden Ansprüche, worin R1 für Wasserstoff, Methyl, Ethyl, n-Propyl, 2-Fluorethyl, 3-Fluorpropyl, 3-Hydroxypropyl, Cyclopropylmethyl oder Allyl steht.
  5. Verbindung nach Anspruch 4, worin R1 für n-Propyl oder Allyl steht.
  6. Verbindung nach einem der vorhergehenden Ansprüche, worin R2, R3 und R4 für H stehen.
  7. Verbindung nach einem der vorhergehenden Ansprüche, worin A unsubstituiert oder durch Halogen substituiert ist.
  8. Verbindung nach einem der vorhergehenden Ansprüche, worin E für NH steht.
  9. Verbindung nach einem der vorhergehenden Ansprüche, worin Ar für Phenyl, Thienyl, Pyridyl, Pyrimidyl, Imidazolyl, Isoxazolyl, Thiazolyl, Triazolyl, Thiadiazolyl, Chinolinyl, Isochinolinyl, Tetrahydroisochinolinyl, Benzofuranyl, Benzothiophenyl, Benzoxazinyl, Benzothiazolyl, Benzoxadiazolyl, Benzothiadiazolyl oder Indanyl steht, die substituiert sein können wie in Anspruch 1 definiert.
  10. Verbindung nach Anspruch 9, worin Ar für Phenyl, 2- oder 3-Thienyl, 2-, 3- oder 4-Pyridyl, 1-, 2-, 3-, 4- oder 5-Indanyl oder 2-, 3-, 4- oder 5-Benzofuranyl steht.
  11. Verbindung nach Anspruch 9, worin Ar für Phenyl, Thienyl, Pyridyl, Benzofuranyl oder Indanyl steht, die substituiert sein können wie in Anspruch 2 definiert.
  12. Verbindung nach einem der Ansprüche 9 bis 11, worin Ar für Phenyl steht, das 1, 2 oder 3 Substituenten trägt, die ausgewählt sind unter Halogen, C1-C6-Alkyl, fluoriertem C1-C4-Alkyl, C1-C4-Alkoxy, fluoriertem C1-C4-Alkoxy, C2-C4-Alkenyl, fluoriertem C2-C4-Alkenyl, CH2N(CH3)2, NR6R7, wobei R6 und R7 jeweils unabhängig voneinander für H, C1-C4-Alkyl oder fluoriertes C1-C4-Alkyl stehen, gegebenenfalls durch Halogen substituiertes C3-C6-Cycloalkyl, Acetyl oder Carboxyl, oder Ar für Thienyl, Pyridyl, Benzofuranyl oder Indanyl steht, die gegebenenfalls durch Halogen, C1-C4-Alkyl oder C1-C4-Alkenyl substituiert sind.
  13. Verbindung nach einem der vorhergehenden Ansprüche, worin Ar einen Rest Ra der Formel Ra' trägt worin Y für N, CH oder CF steht, Ra1 und Ra2 unabhängig voneinander ausgewählt sind unter C1-C2-Alkyl, fluoriniertem C1-C2-Alkyl und C1-C2-Alkoxy, unter der Maßgabe, dass wenn Y für CH oder CF steht, einer der Reste Ra1 oder Ra2 auch für Wasserstoff oder Fluor stehen kann, oder Ra1 und Ra2 zusammen einen Rest (CH2)m bilden, worin 1 oder 2 der Wasserstoffatome durch Fluor, Hydroxy, C1-C2-Alkyl oder C1-C2-Alkoxy ersetzt sein können, worin eine CH2-Gruppe durch O, S, SO, SO2 oder N-Rc, worin Rc für H oder C1-C2-Alkyl steht, ersetzt sein kann und worin m für 2, 3, 4, 5 oder 6 steht.
  14. Verbindung nach Anspruch 13, worin der Rest Ra' ausgewählt ist unter Isopropyl, (R)-1-Fluorethyl, (S)-1-Fluorethyl, 2-Fluorethyl, 1,1-Difluorethyl, 2,2-Difluorethyl, 2,2,2-Trifluorethyl, (R)-1-Fluorpropyl, (S)-1-Fluorpropyl, 2-Fluorpropyl, 3-Fluorpropyl, 1,1-Difluorpropyl, 2,2-Difluorpropyl, 3,3-Difluorpropyl, 3,3,3-Trifluorpropyl, (R)-2-Fluor-1-methylethyl, (S)-2-Fluor-1-methylethyl, (R)-2,2-Difluor-1-methylethyl, (S)-2,2-Difluor-1-methylethyl, (R)-1,2-Difluor-1-methylethyl, (S)-1,2-Difluor-1-methylethyl, (R)-2,2,2-Trifluor-1-methylethyl, (S)-2,2,2-Trifluor-1-methylethyl, 2-Fluor-1-(fluormethyl)ethyl, 1-(Difluormethyl)-2,2-difluorethyl, Cyclopropyl, Cyclobutyl, 1-Fluorcyclopropyl, 2-Fluorcyclopropyl, (S)-2,2-Difluorcyclopropyl und (R)-2,2-Difluorcyclopropyl.
  15. Verbindung nach einem der Ansprüche 13 oder 14, worin der Rest Ra' 1, 2, 3 oder 4 Fluoratome aufweist.
  16. Verbindung nach einem der vorhergehenden Ansprüche, worin Ar für Phenyl steht, das einen Rest Ra in der 4-Position des Phenylrings aufweist.
  17. Verbindung nach einem der vorhergehenden Ansprüche, worin die absolute Konfiguration am Kohlenstoffatom, das die Gruppe A trägt, (S) ist.
  18. Verbindung nach einem der Ansprüche 1, 3 bis 10, 16 oder 17, worin Ar für Phenyl steht, das durch einen 5- oder 6 gliedrigen heterocyclischen Rest substituiert ist, der ausgewählt ist unter Azetidinyl, Pyrrolidinyl, Oxopyrrolidinyl, Oxo-oxazolidinyl, Piperidinyl, Piperazinyl, Morpholinyl, Thiomoroholinyl, 1-Oxothiomorpholinyl, 1,1-Dioxothiomorpholinyl, Pyrrolyl, Furanyl, Thienyl, Pyrazolyl, Imidazolyl, Oxazolyl, Isoxazolyl, Triazolyl, Oxadiazolyl, Furazanyl, Thiadiazolyl und Tetrazolyl, wobei der heterocyclische Rest unsubstituiert sein oder 1 bis 3 Substituenten, ausgewählt unter Halogen, C1-C4-Alkyl, fluoriertem C1-C4-Alkyl, C1-C4-Alkoxy und Hydroxy, aufweisen kann.
  19. Verbindung nach Anspruch 18, worin Ar für Phenyl steht, das durch einen 5- oder 6-gliedrigen heterocyclischen Rest, ausgewählt unter Azetidinyl, Pyrrolidinyl, Oxopyrrolidinyl, Oxooxazolidinyl, Morpholinyl, Furanyl, Thienyl, Pyrazolyl, Oxazolyl, Isoxazolyl und Thiadiazolyl substituiert ist, wobei der heterocyclische Rest unsubstituiert sein oder 1 bis 3 Substituenten, ausgewählt unter Halogen und C1-C4-Alkyl, aufweisen kann.
  20. Pharmazeutisches Mittel, enthaltend wenigstens eine Verbindung nach einem der vorherigen Ansprüche, gegebenenfalls zusammen mit wenigstens einem physiologisch akzeptablen Träger oder Hilfsstoff.
  21. Verwendung einer Verbindung nach einem der Ansprüche 1 bis 19 zur Herstellung eines pharmazeutischen Mittels zur Behandlung von Erkrankungen, die auf die Beeinflussung durch einen Dopamin-D3-Rezeptorliganden ansprechen.
  22. Verwendung nach Anspruch 21, wobei die Erkrankung eine Erkrankung des zentralen Nervensystems ist.
HK08100350.6A 2004-10-14 2005-10-14 Heterocyclic compounds suitable for treating disorders that respond to modulation of the dopamine d3 receptor HK1111681B (en)

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