CA2352526A1 - Use of n-substituted azabicycloalkane derivatives for treating diseases of the central nervous system - Google Patents

Use of n-substituted azabicycloalkane derivatives for treating diseases of the central nervous system Download PDF

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CA2352526A1
CA2352526A1 CA002352526A CA2352526A CA2352526A1 CA 2352526 A1 CA2352526 A1 CA 2352526A1 CA 002352526 A CA002352526 A CA 002352526A CA 2352526 A CA2352526 A CA 2352526A CA 2352526 A1 CA2352526 A1 CA 2352526A1
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azabicyclo
exo
ethyl
fluorophenyl
heptan
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CA002352526A
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French (fr)
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Gerd Steiner
Rainer Munschauer
Gerhard Gross
Martin Traut
Liliane Unger
Hans-Jurgen Teschendorf
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Abbott GmbH and Co KG
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    • 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
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
    • 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
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • 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
    • 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
    • A61P25/28—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
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
    • 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
    • A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
    • A61P25/36—Opioid-abuse

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  • Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Biomedical Technology (AREA)
  • Neurosurgery (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Neurology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Addiction (AREA)
  • Psychiatry (AREA)
  • Epidemiology (AREA)
  • Hospice & Palliative Care (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Indole Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

Abstract

The invention relates to the use of N-substituted 3-azabicycloalkane derivatives of formula (I), wherein B, R1, R2 and n have the meanings given in the description, for combating diseases of addiction and other diseases of the central nervous system.

Description

USE OF N-SUBSTITUTED AZABICYCLOALKANE DERIVATIVES FOR
TREATING DISEASES OF THE CENTRAL NERVOUS SYSTEM
N-substituted azabicycloalkane derivatives are already known as neuroleptics (WO 95/13279, WO 95/15327, WO 96/04272, US
5.475.105, US 5.521.209, US 5.616.705, US 5.753.690). It has now been found that these substances are also suitable for controlling addictive disorders and other disorders of the central nervous system.
The present invention provides the use of N-substituted 3-azabicycloalkane derivatives of the formula I

N-( GHy ) n-R2 in which B is a 4-, 5- or 6-membered ring, which may contain a double bond, R1 is a phenyl, naphthyl, phenanthryl or thienyl group, in. each case unsubstituted or mono- or disubstituted by halogen atoms, C1-4-alkyl, trifluoromethyl, hydroxyl, C1_4-alkoxy, ariino, monomethylamino, dimethylamino, cyano or nitro groups, n is the number 0, 1, 2, 3 or 4 and RZ is a naphthyl group which is unsubstituted or substituted by one or two halogen atoms, or is one of the following radicals:

'' 0050/49558 CA 02352526 2001-05-23 R5 ~ NR6 C R~ ~ NR6 SOp O
.

6- ~~ R8 ~ Rs Rs -NR C O~ ~ -O-C O ' -O O
_ Rs -N /O Rs -.0 O . ~ --N
O
O
Rs N ~ O R9 O
- N~
~- R1~ -N 0 , ~R8 . -N
~~ Rs .
Rs ~ O
-_t3 ~N ~ ~~CH3 R11 ~N R9 ~N~~ .
. ..
H3C N~N/ . X .Y

Rs -N~ or -N O
in which R3 is a hydrogen atom, a hydroxyl group or a phenyl radical which is unsubstituted or substituted by a fluorine, chlorine or bromine atom, R4 is a hydrogen atom or R3 and R4 together are an oxygen atom, ' 0050/49558 R5 is a phenyl, naphthyl or thienyl group, each of which is unsubstituted or mono- or disubstituted by fluorine, chlorine or bromine atoms or by hydroxyl, vitro, amino, C1_q-alkanoylamino, C1_q-alkylamino, C1_q-alkyl or methoxy groups, R6 is a hydrogen atom or a methyl group, R~ is a phenyl, naphthyl, benzofuryl, benzothienyl, thienyl, indolyl, N-methylindolyl or indenyl group, in each case unsubstituted or mono- or disubstituted by fluorine, chlorine or bromine atoms or by C1_q-alkyl, hydroxyl, methoxy, vitro, cyano, trifluoromethyl, amino or di-C1_q-alkylamino groups, or is a C3_~-cycloalkyl group, R8 is a hydrogen atom or a fluorine or chlorine atom or a Ci-q-alkyl, methoxy or amino group, R9 is a hydrogen atom or a methyl group and R1~ is a hydrogen atom or a methyl group or R9 and Rlo together with the ring carbon atom are a spirocyclopropane ring, R11 is a hydrogen atom, a hydroxyl, C1-Cq-alkyl or C~-C4-alkoxy group, or together with the adjacent carbon atom is a C=O- or C=S group, X and Y are carbon atoms, CH, CH2, NH or C1-Cq-alkyl-N groups or nitrogen atoms, Z is a direct bond, a CO group, CS group or a CH or CH2 group in which a hydrogen atom may be replaced by a hydroxyl, amino or C1-Cq-alkoxy group or by a halogen atom, and A is a hydrogen atom, a hydroxyl, amino, mercapto, C1-Cq-alkylamino, di-C1-Cq-alkylamino, C1-Cq-alkylthio or CZ-Cq-alkoxy group or together with the adjacent carbon atom is a C=0 group or A is a Y-bonded C3-Cq-alkylene group which may contain one or two non-cumulated double bonds and in which one CH or CH2 group may be replaced by a nitrogen or sulfur atom or an NH
or N-CH3 group and where the ring is either monosubstituted by a fluorine or chlorine atom or a methyl, methoxy, vitro or amino group or, in the case of a benzene ring, this may be 0050/49558 ~ 02352526 2001-05-23 mono-, di- or trisubstituted by fluorine or chlorine atoms or methyl, trifluoromethyl, nitro, hydroxyl, methoxy, amino, monomethyl or dimethylamino groups, and in which the X-, Y- and Z-containing ring at the nitrogen atom No. 1 may carry a C1-C4-alkyl, allyl or benzyl group and may contain 1 to 3 non-cumulated double bonds, and their salts with physiologically acceptable acids for preparing medicaments for controlling addiction, for treating concentration disorders (attention deficit disorders), hyperactivity in children (attention deficit hyperactivity disorders), learning and memory weaknesses (impaired cognitive function).
The use according to the invention relates to all addictive disorders, whether they are caused by abuse of substances or other addictive disorders such as, for example, addiction to gambling. Habit-forming substances can be:
opioids such as, for example, morphine or heroin, nicotine, alcohol, substances which interact with the benzodiazepine receptor complex, sedatives or tranquilizers, such as, for example, the benzodiazepines.
Possible habit-forming substances according to the invention are, in particular, cocaine or amphetamine and amphetamine-like substances.
The compounds of the formula I can be employed both in the form of their racemates and their optical isomers.
For the novel indication, the compounds can be administered in a customary manner orally or parenterally, intravenously or intramuscularly.
The dosage depends on the age, condition and weight of the patient and on the type of administration. In general, the daily dose of active compound is between about 1 and 100 mg/kg of bodyweight in the case of oral administration and between 0.1 and 10 mg/kg of bodyweight in the case of parenteral administration.
The compounds can be employed in customary pharmaceutical administration forms, in solid or liquid form, for example as tablets, film-coated tablets, capsules, powders, granules, 0050/49558 ~ 02352526 2001-05-23 sugar-coated tablets, suppositories, solutions, ointments, creams or sprays. These are prepared in a customary manner. For this purpose, the active compounds can be processed with the customary pharmaceutical auxiliaries such as tablet binders, fillers, 5 preservatives, tablet disintegrants, flow regulators, plasticizers, wetting agents, dispersants, emulsifiers, solvents, release-delaying agents, antioxidants and/or propellants (cf. H.
Sucker et al.: Pharmazeutische Technologie [Pharmaceutical Technology], Thieme-Verlag, Stuttgart, 1978). The resulting administration forms usually comprise the active compound in an amount of from 1 to 99% by weight.
The following substances may be mentioned as examples of compounds of the formula I:
1. 1-(4-fluorophenyl)-4-[exo-6-phenyl-3-azabicyclo[3.2.0]-heptan-3-yl]butan-1-one 2. 1-phenyl-4-[exo-6-phenyl-3-azabicyclo[3.2.Ojheptan-3-yl]-butan-1-one 3. 1-(4-fluorophenyl)-4-[exo-6,7-diphenyl-3-azabicyclo-[3.2.0]heptan-3-yljbutan-1-one 4. 1-(4-fluorophenyl)-4-[exo-6-phenyl-3-azabicyclo[3.2.0j-heptan-3-yljbutane 5. 1-phenyl-2-[exo-6-phenyl-3-azabicyclo[3.2.0]heptan-3-yl]-ethan-1-one 6. 1-(4-fluorophenyl)-4-[exo-6-p-fluorophenyl-3-azabicyclo-[3.2.0]heptan-3-yl]butane 7. 1-(4-fluorophenyl)-4-[exo-6-m-fluorophenyl-3-azabicyclo-[3.2.0)heptan-3-yl]butan-1-one 8. 1-(4-fluorophenyl)-4-[exo-6-o-fluorophenyl-3-azabicyclo-[3.2.0]heptan-3-yl]butan-1-one 9. 1-(4-fluorophenyl)-4-[exo-6-p-chlorophenyl-3-azabicyclo-[3.2.0]heptan-3-yl]butan-1-one 10. 1-(4-fluorophenyl)-4-[exo-6-m-chlorophenyl-3-azabicyclo-[3.2.Ojheptan-3-yl]butan-1-one ~~50/49558 ~ 02352526 2001-05-23 11. 1-(4-fluorophenyl)-4-[exo-6-p-methoxyphenyl-3-azabicyclo-[3.2.0]heptan-3-yl]butan-1-one 12. 1-(4-fluorophenyl)-4-[exo-6-m,p-dichlorophenyl-3-azabicyclo-[3.2.0]heptan-3-yl]butan-1-one 13. 1-(4-fluorophenyl)-4-[exo-6-m,p-dimethoxyphenyl-3-aza-bicyclo[3.2.0]heptan-3-yl]butan-1-one 14. 1-(4-fluorophenyl)-4-[exo-6-p-fluorophenyl-3-azabicyclo-[3.2.0]heptan-3-yl]butan-1-one 15. 1-phenyl-4-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]-heptan-3-yl]butan-1-one 16. 1-(4-fluorophenyl)-4-[exo-6-p-fluorophenyl-3-azabicyclo-[3.2.0]heptan-3-yl]butane 17. 1-(4-fluorophenyl)-4-[exo-6-p-nitrophenyl-3-azabicyclo-[3.2.0]heptan-3-yl]butan-1-one 18. 1-(4-fluorophenyl)-4-[exo-6-m-nitrophenyl-3-azabicyclo-[3.2.0]heptan-3-yl]butan-1-one 19. 1-(4-fluorophenyl)-4-[exo-6-p-trifluoromethylphenyl-3-azabicyclo[3.2.0]heptan-3-yl]butan-1-one 20. I-(4-fluorophenyl)-4-[exo-6-p-cyanophenyl-3-azabicyclo-[3.2.0]heptan-3-yl]butan-1-one 21. 1-(4-fluorophenyl)-4-[exo-6-thien-3-yl-3-azabicyclo-[3.2.0]heptan-3-yl]butan-1-one 22. 1-(4-fluorophenyl)-4-[exo-6-pyrid-3-yl-3-azabicyclo-[3.2.0]heptan-3-yl]butan-1-one 23. 1-(4-fluorophenyl)-3-[exo-6-p-fluorophenyl-3-azabicyclo-[3.2.0]heptan-3-yl]propan-1-one 24. 1-(bis-4-fluorophenyl)-4-[exo-6-p-fluorophenyl-3-azabicyclo-[3.2.0]heptan-3-yl]butane 25. 1-(bis-4-fluorophenyl)-4-[exo-6-phenyl-3-azabicyclo-[3.2.0]heptan-3-yl]butane 26. 1-(4-fluorophenyl)-4-[exo-6-phenyl-3-azabicyclo[3.2.0]-heptan-3-yl]butan-1-of 27. 1-(4-fluorophenyl)-4-[exo-6-p-fluorophenyl-3-azabicyclo-[3.2.0]heptan-3-yl]butan-1-of 28. 1-(4-fluorophenyl)-4-[exo-6,7-Biphenyl-3-azabicyclo[3.2.0]-heptan-3-yl]butan-I-of 29. 1-phenyl-4-[exo-6-phenyl-3-azabicyclo[3.2.0]heptan-3-yl]-butan-1-of 30. 1-phenyl-4-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]-heptan-3-yl]butan-1-of 31. 1-(4-fluorophenyl)-4-[exo-6-o-fluorophenyl-3-azabicyclo-[3.2.0]heptan-3-yl]butan-1-of 32. 1-(4-fluorophenyl)-4-[exo-6-m-chlorophenyl-3-azabicyclo-[3.2.0]heptan-3-yl]butan-1-of 33. 1-(4-fluorophenyl)-4-[exo-6-p-trifluoromethylphenyl-3-azabicyclo[3.2.0]heptan-3-yl]butan-1-of 34. 1-(4-fluorophenyl)-4-[exo-6-p-aminophenyl-3-azabicyclo-[3.2.0]heptan-3-yl]butan-1-one 35. N-(3-[exo-6-phenyl-3-azabicyclo[3.2.0]heptan-3-yl]propyl)-4-fluorobenzamide 36. N-(3-[exo-6-phenyl-3-azabicyclo[3.2.0]heptan-3-yl]-propyl)benzamide 37. N-(2-[exo-6-phenyl-3-azabicyclo[3.2.0]heptan-3-yl]-ethyl)-4-fluorobenzamide 38. N-(2-[exo-6-phenyl-3-azabicyclo[3.2.0]heptan-3-yl]-ethyl)benzamide 39. N-(2-[exo-6-phenyl-3-azabicyclo[3.2.0]heptan-3-yl]-ethyl)-N-methyl-4-fluorobenzamide 40. N-(2-[exo-6-phenyl-3-azabicyclo[3.2.0]heptan-3-yl]-ethyl)-N-methylbenzamide 41. N-(2-[exo-6-phenyl-3-azabicyclo[3.2.0]heptan-3-yl]-ethyl)-N-methyl-4-isopropylbenzamide 42. N-(3-[exo-6-phenyl-3-azabicyclo[3.2.0]heptan-3-yl]-propyl)-4-chlorobenzamide 43. N-(2-[exo-6-p-trifluoromethylphenyl-3-azabicyclo[3.2.0]-heptan-3-yl]ethyl)-4-chlorobenzamide 44. N-(3-[exo-6-phenyl-3-azabicyclo[3.2.0]heptan-3-yl]-propyl)-3-methoxybenzamide 45. N-(3-[exo-6-phenyl-3-azabicyclo[3.2.0]heptan-3-yl]-propyl)-3-nitrobenzamide 46. N-(3-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]propyl)-4-fluorobenzamide 47. N-(3-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]propyl)benzamide 48. N-(2-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]ethyl)-4-fluorobenzamide~
49. N-(2-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]ethyl)benzamide 50. N-(2-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]ethyl)-N-methyl-4-fluorobenzamide 51. N-(2-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]ethyl)-N-methylbenzamide 52. N-(2-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]ethyl)-N-methyl-4-isopropylbenzamide 53. N-(3-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]propyl)-4-chlorobenzamide 54. N-(3-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]propyl)-3-methoxybenzamide 55. N-(3-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]propyl)-3-nitrobenzamide 56. N-(2-[exo-6-m-chlorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]ethyl)-4-chlorobenzamide 57. N-(2-[exo-6-o-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl)ethyl)-4-chlorobenzamide 58. N-(2-(exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]ethyl)-2-hydroxybenzamide 59. N-(2-[exo-6-m-hydroxyphenyl-3-azabicyclo[3.2.0]heptan-3-yl]-ethyl)-4-chlorobenzamide 60. exo-3-n-butyl-6-phenyl-3-azabicyclo[3.2.0)heptane 61. exo-3-methyl-6-phenyl-3-azabicyclo[3.2.0]heptane 62, exo-3-methyl-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptane 63. exo-3-n-propyl-6-p-fluorophenyl-3-azabicyclo[3.2.0]-heptane 64. exo-3-methyl-6,7-diphenyl-3-azabicyclo[3.2.0]heptane 65. exo-3-n-propyl-6-m-hydroxyphenyl-3-azabicyclo[3.2.0]-heptane 66, exo-3-allyl-6-m-methoxyphenyl-3-azabicyclo[3.2.0]-heptane 67. exo-3-(3,4-dimethoxy)phenethyl-6-phenyl-3-azabicyclo-[3.2.0]heptane 68. exo-3-(3,4-dimethoxy)phenethyl-6-p-fluorophenyl-3-azabicyclo(3.2.0)heptane 69. exo-3-(3,4-dihydroxy)phenethyl-3-azabicyclo[3.2.0]-heptane 70. exo-3-phenethyl-6-p-fluorophenyl-3-azabicyclo[3.2.0]-heptane 71. 6-~-[exo-6-p-fluorophenyl-3-azabicyclo(3.2.0]heptan-3-yl)-ethyl-7-methyl-SH-thiazolo[3,2-a]pyrimidin-5-one 72. (+)-6-~-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl)ethyl-7-methyl-5H-thiazolo[3,2-a]pyrimidin-5-one 73. (-)-6-~-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan 3-yljethyl-7-methyl-5H-thiazolo[3,2-a]pyrimidin-5-one 74. 6-~-[exo-6-phenyl-3-azabicyclo[3.2.0]heptan-3-yl]ethyl-7-5 methyl-5H-thiazolo[3,2-a]pyrimidin-5-one 75. 6-~-[exo-6,7-diphenyl-3-azabicyclo[3.2.0]heptan-3-yljethyl-7-methyl-5H-thiazolo[3,2-a]pyrimidin-5-one 10 76. 6-~-[exo-6,7-bis-(p-fluorophenyl)-3-azabicyclo[3.2.0]heptan 3-yl]ethyl-7-methyl-5H-thiazolo[3,2-a]pyrimidin-5-one 77. 6-~-[exo-6-m-chlorophenyl-3-azabicyclo[3.2.0]heptan-3-ylj-ethyl-7-methyl-5H-thiazolo[3,2-a]pyrimidin-5-one 78. 6-~-[exo-6-m-methoxyphenyl-3-azabicyclo[3.2.0]heptan-3-yl]-ethyl-7-methyl-5H-thiazolo[3,2-a]pyrimidin-5-one 79. 6-~-[exo-6-m-hydroxyphenyl-3-azabicyclo[3.2.0]heptan-3-yl]ethyl-7-methyl-5H-thiazolo[3,2-a]pyrimidin-5-one 80. 6-~-(2-[exo-6-p-aminophenyl-3-azabicyclo[3.2.Ojheptan-3-yl]ethyl-7-methyl-5H-thiazolo[3,2-a]pyrimidin-5-one 81. 6-~-[exo-6-p-chlorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]ethyl-7-methyl-5H-thiazolo[3,2-a]pyrimidin-5-one 82..6-~-[exo-6-p-methoxyphenyl-3-azabicyclo[3.2.0]heptan 3-yl]ethyl-7-methyl-5H-thiazolo[3,2-a]pyrimidin-5-one 83. 6-~-[exo-6-p-nitrophenyl-3-azabicyclo[3.2.0]heptan-3-yl]ethyl-7-methyl-5H-thiazolo[3,2-a]pyrimidin-5-one 84. 6-B-[exo-6-m-fluorophenyl-3-azabicyclo[3.2.0jheptan-3-yl]ethyl-7-methyl-5H-thiazolo[3,2-a]pyrimidin-5-one 85. 6-~-[exo-6-p-hydroxyphenyl-3-azabicyclo[3.2.0]heptan-3-yl]ethyl-7-methyl-5H-thiazolo[3,2-a]pyrimidin-5-one 86. 6-~-[exo-6-p-trifluoromethylphenyl-3-azabicyclo[3.2.0]-heptan-3-yl]ethyl-7-methyl-5H-thiazolo[3,2-a]pyrimidin-5-one 87. 6-~-[exo-6-(p-t-butylphenyl)-3-azabicyclo[3.2.0]heptan-3-yl]ethyl-7-methyl-5H-thiazolo[3,2-a]pyrimidin-5-one 88. 6-B-[endo-6-(p-t-butylphenyl)-3-azabicyclo[3.2.0)heptan 3-yl]ethyl-7-methyl-5H-thiazolo[3,2-a]pyrimidin-5-one 89. 6-~-[exo-6-(3,4-dichlorophenyl)-3-azabicyclo[3.2.0]heptan-3-yl)ethyl-7-methyl-5H-thiazolo[3,2-a]pyrimidin-5-one 90. 6-~-[exo-6-(3,4-dimethoxyphenyl)-3-azabicyclo[3.2.0]-heptan-3-yl]ethyl-7-methyl-5H-thiazolo[3,2-a]pyrimidin-5-one 91. 6-~-[exo-6-p-cyanophenyl-3-azabicyclo[3.2.0)heptan-3-yl]ethyl-7-methyl-5H-thiazolo[3,2-a]pyrimidin-5-one 92. 6-~-[exo-6-(3,4-dihydroxyphenyl)-3-azabicyclo[3.2.0]-heptan-3-yl]ethyl-7-methyl-5H-thiazolo[3,2-a]pyrimidin-5-one 93. 6-~-[exo-6-(o-fluorophenyl)-3-azabicyclo[3.2.0]heptan-3-yl]ethyl-7-methyl-5H-thiazolo[3,2-a]pyrimidin-5-one 94. 6-~-[exo-6-thien-3-yl-3-azabicyclo[3.2.0]heptan-3-yl]-ethyl-7-methyl-5H-thiazolo[3,2-a]pyrimidin-5-one 95. 6-B-[exo-6-(5-chlorothien-2-yl)-3-azabicyclo[3.2.0]heptan-3-yl]ethyl-7-methyl-5H-thiazolo[3,2-a]pyrimidin-5-one 96. 6-~-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]-ethyl-7-methyl-2,3-dihydro-5H-thiazolo[3,2-a]pyrimidin-5-one 97. 6-~-[exo-6-m-chlorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]-ethyl-7-methyl-2,3-dihydro-5H-thiazolo[3,2-a]pyrimidin-5-one 98. 6-B-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]-ethyl-2,3,7-trimethyl-5H-thiazolo[3,2-a)pyrimidin-5-one 99. 6-B-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl)-ethyl-5H-thiazolo[3,2-a]pyrimidin-5-one 100.6-~-[exo-6-phenyl-3-azabicyclo[3.2.0]heptan-3-yl]ethyl-5H-thiazolo[3,2-a]pyrimidin-5-one 101.7-~-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]-ethyl-8-methyl-2H,6H-pyrimido[2,1-b][1,3]thiazin-6-one 102.7-~-[exo-6-phenyl-3-azabicyclo[3.2.0]heptan-3-yl]ethyl-8-methyl-2H,6H-pyrimido[2,1-b][1,3]thiazin-6-one 103.7-H-[exo-6-m-chlorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]-ethyl-8-methyl-2H,6H-pyrimido[2,1-b][1,3]thiazin-6-one 104.7-~-[exo-6-p-chlorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]
ethyl-8-methyl-2H,6H-pyrimido[2,1-b][1,3]thiazin-6-one 105.7-~-[exo-6-p-methoxyphenyl-3-azabicyclo[3.2.0]heptan-3-yl]-ethyl-8-methyl-2H,6H-pyrimido[2,1-b][1.3]thiazin-6-one 106.7-~-[exo-6-m-hydroxyphenyl-3-azabicyclo[3.2.0]heptan-3-yl]-ethyl-8-methyl-2H,6H-pyrimido[2,1-b][1,3]thiazin-6-one 107.3-H-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]-ethyl-2,4-(1H,3H)quinazolinedione 108.(+)-3-H-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]ethyl-2,4-(1H,3H)quinazolinedione 109.(-)-3-H-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]ethyl-2,4-(1H,3H)quinazolinedione 110.3-~-[exo-6-phenyl-3-azabicyclo[3.2.0]heptan-3-yl]ethyl-2,4-(1H,3H)quinazolinedione 111.3-H-[exo-6-m-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]-ethyl-2,4-(1H,3H)quinazolinedione 112.3-H-[exo-6-p-cyanophenyl-3-azabicyclo[3.2.0]heptan-3-yl]-ethyl-2,4-(1H,3H)quinazolinedione 113.3-H-[exo-6-m-chlorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]-ethyl-2,4-(1H,3H)quinazolinedione 114.3-~-[exo-6-p-hydroxyphenyl-3-azabicyclo[3.2.0]heptan-3-yl]-ethyl-2,4-(1H,3H)quinazolinedione 115.3-~-[exo-6-p-chlorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]-ethyl-2,4-(1H,3H)quinazolinedione 116.3-~-[exo-6-m-methoxyphenyl-3-azabicyclo[3.2.0]heptan-3-yl]-ethyl-2,4-(1H,3H)quinazolinedione 0050/49558 ~ 02352526 2001-05-23 117.3-f3-[exo-6-p-nitrophenyl-3-azabicyclo[3.2.0]heptan-3-yl]
ethyl-2,4-(iH,3H)quinazolinedione 118.3-J3-[endo-6-p-nitrophenyl-3-azabicyclo[3.2.0]heptan-3-yl]-ethyl-2,4-(1H,3H)quinazolinedione 119.3-!3-[exo-6-m-hydroxyphenyl-3-azabicyclo[3.2.0]heptan-3-yl]-ethyl-2,4-(1H,3H)quinazolinedione 120.3-!3-[exo-6-p-aminophenyl-3-azabicyclo[3.2.0]heptan-3-yl)-ethyl-2,4-(1H,3H)quinazolinedione 121.3-fi-[exo-6-p-iodophenyl-3-azabicyclo[3.2.0]heptan-3-yl)-ethyl-2,4-(1H,3H)quinazolinedione 122.3-I3-[exo-6-p-trifluoromethylphenyl-3-azabicyclo[3.2.0]-heptan-3-yl]ethyl-2,4-(1H,3H)quinazolinedione 123.3-fi-[exo-6-(3,4-dichlorophenyl)-3-azabicyclo[3.2.0]-heptan-3-yl]ethyl-2,4-(1H,3H)quinazolinedione 124.3-!3-[exo-6-(3,4-dihydroxyphenyl)-3-azabicyclo[3.2.0]-heptan-3-yl]ethyl-2,4-(1H,3H)quinazolinedione ?5 125.3-!3-[exo-6-(3,5-dichlorophenyl)-3-azabicyclo[3.2.0]heptan-3-yl]ethyl-2,4-(1H,3H)quinazolinedione 126.3-!3-[exo-6-o-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]-ethyl-2,4-(1H,3H)quinazolinedione 127.3-!3-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]-ethyl-8-methyl-2,4-(1H,3H)quinazolinedione 128.3-!3-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]-ethyl-7-chloro-2,4-(1H,3H)quinazolinedione 129.3-J3-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]-ethyl-7-fluoro-2,4-(1H,3H)quinazolinedione 130.3-!3-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]-ethyl-5-chloro-2,4-(1H,3H)quinazolinedione 131.3-!i-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]-ethyl-6-fluoro-2,4-(1H,3H)quinazolinedione 0050/49558 ~ 02352526 2001-05-23 132.3-J3-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]-ethyl-6-methyl-2,4-(1H,3H)quinazolinedione 133.3-!3-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]-ethyl-8-methoxy-2,4-(1H,3H)quinazolinedione 134.3-f3-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]-ethyl-6-trifluoromethyl-2,4-(1H,3H)quinazolinedione 135.3-!3-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]-ethyl-7-vitro-2,4-(1H,3H)quinazolinedione 136.3-l3-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]-ethyl-6-vitro-2,4-(1H,3H)quinazolinedione 137.3-!3-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0)heptan-3-yl]-ethyl-7-amino-2,4-(1H,3H)quinazolinedione 138.3-J3-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]-ethyl-6-amino-2,4-(1H,3H)quinazolinedione 139.3-l3-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]-ethyl-6-hydroxy-2,4-(1H,3H)quinazolinedione 140.3-!i-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]-ethyl-5-chloro-2,4-(1H,3H)quinazolinedione 141.3-l3-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]-ethyl-6,7-dimethoxy-2,4-(1H,3H)quinazolinedione 142.3-!3-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]-ethyl-6,8-dichloro-2,4-(1H,3H)quinazolinedione 143.3-!3-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]-ethyl-6,7,8-trimethoxy-2,4-(1H,3H)quinazolinedione 144.3-B-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]-ethyl-1-methyl-2,4-(1H,3H)quinazolinedione 145.3-!3-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]-ethyl-1-ethyl-2,4-(1H,3H)quinazolinedione 146.3-!3-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]-ethyl-1-allyl-2,4-(1H,3H)quin~zolinedione 147.3-H-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]-ethyl-1-benzyl-2,4-(1H,3H)quinazolinedione 148.3-y-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]-5 propyl-2,4-(1H,3H)quinazolinedione 149.3-b-(exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]-butyl-2,4-(1H,3H)quinazolinedione 10 150.3-~-[exo-6-(2-thienyl)-3-azabicyclo[3.2.0]heptan-3-yl]-ethyl-2,4-(1H,3H)quinazolinedione 151.3-~-(exo-6-(5-chloro-2-thienyl)-3-azabicyclo[3.2.0]heptan-3-yl]ethyl-2,4-(1H,3H)quinazolinedione 152.3-~-[exo-6-(3-thienyl)-3-azabicyclo[3.2.0]heptan-3-yl]-ethyl-2,4-(1H,3H)quinazolinedione 153.3-H-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]-ethyl-1H-thieno[3,2-d]pyrimidine-2,4-dione 154.3 -~-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]-ethyl-1H-thieno[2,3-d]pyrimidine-2,4-dione 155.3-~-[exo-6-p-fluorophenyl-3-azabicyclo(3.2.0]heptan-3-yl]-ethyl-1H-thieno(3,4-d]pyrimidine-2,4-dione 156.3-~-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]
ethyl-1-methyl-1H,3H-pyrido[2,3-d]pyrimidine-2,4-dione 157.3-~-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]-ethyl-2-methyl-3H-quinazolin-4-one 158.3-~-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]-ethyl-2-methoxy-3H-quinazolin-4-one 159.3-~-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]-ethyl-2-methyl-4H-pyrido(1,2-a]pyrimidin-4-one dihydrochloride 160.3-B-[exo-6-phenyl-3-azabicyclo[3.2.0]heptan-3-yl]ethyl-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one 161.3-~-[exo-6-m-chlorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]-ethyl-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one 0050/49558 ~ 02352526 2001-05-23 162.3-f3-[exo-6-m-methoxyphenyl-3-azabicyclo[3.2.0]heptan-3-yl]ethyl-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one 163.3-13-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan 3-yl)ethyl-2,6-dimethyl-4H-pyrido[1,2-a]pyrimidin-4-one 164.3-t3-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]ethyl-2,7-dimethyl-4H-pyrido[1,2-a]pyrimidin-4-one 165.3-J3-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]ethyl-2,8-dimethyl-4H-pyrido[1,2-a]pyrimidin-4-one 166.3-!3-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl)ethyl-2,9-dimethyl-4H-pyrido[1,2-a]pyrimidin-4-one 167.3-!3-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]ethyl-2,6,8-trimethyl-4H-pyrido[1,2-a]pyrimidin-4-one 168.3-!3-[exo-6-m-chlorophenyl-3-azabicyclo[3.2.0]heptan 3-yl]ethyl-2,7-dimethyl-4H-pyrido[1,2-a]pyrimidin-4-one 169.3-13-[exo-6-o-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]ethyl-2,7-dimethyl-4H-pyrido[1,2-a]pyrimidin-4-one 170.3-fi-[exo-6-phenyl-3-azabicyclo[3.2.0]heptan-3-yl]ethyl-2,8-dimethyl-4H-pyrido[1,2-a)pyrimidin-4-one 171.3-!3-[exo-6-m-chlorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]ethyl-2,9-dimethyl-4H-pyrido[1,2-a]pyrimidin-4-one 172.3-13-[exo-6-(5-chlorothien-2-yl)-3-azabicyclo[3.2.0]heptan-3-yl)ethyl-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one 173.3-!3-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]-ethyl-6,7,8,9-tetrahydro-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one 174.3-!3-[exo-6-p-chlorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]-ethyl-6,7,8,9-tetrahydro-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one 175.3-J3-[exo-6-p-methoxyphenyl-3-azabicyclo[3.2.0]heptan-3-yl]-ethyl-6,7,8,9-tetrahydro-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one 176.3-5-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]-ethyl-2-methyl-4H-pyrimido[1,2-a]pyrimidin-4-one 177.3-~-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-ylj-ethyl-2-methyl-7-chloro-4H-pyrimido[1,2-a]pyrimidin-4-one 178.6-8-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]-ethyl-7-methyl-1H,5H-imidazo[1,2-a]pyrimidin-5-one 179.3-~-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.Ojheptan-3-yl]-ethyl-2-methyl-7,8-dihydro-4H,6H-pyrrolo[1,2-a]pyrimidin-4-one 180.2-(exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]-methylbenzimidazole 181.1-~-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-ylj-ethylbenzimidazale 182.1-~-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]-ethyl-2,3-dihydrobenzimidazol-2-one 183.2-[exo-6-m-methoxyphenyl-3-azabicyclo[3.2.0]heptan-3-ylj-methylbenzimidazole 184.3-~-(exo-6-p-fluorophenyl-3-azabicyclo[3.2.Ojheptan-3-yl]-ethylindole, m.p. 193-195~C (hydrochloride) 185.3-~-(2-[exo-6-m-chlorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]ethylindole 186.3-~-[exo-6-phenyl-3-azabicyclo[3.2.0]he tan-3- 1 eth 1-P Y j Y
indole, m.p. 104-105~C (hydrochloride) 187.3-~-[exo-6-m-methoxyphenyl-3-azabicyclo[3.2.0]heptan-3-yl]-ethylindole I88.2-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]-methyl-3,4-dihydroquinazolin-4-one 189.2-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]-methyl-3,4-dihydroquinazoline-4-thione 190.2-[exo-6-phenyl-3-azabicyclo[3.2.0]heptan-3-yI]methyl-3,4-dihydroquinazolin-4-one 191.2-[exo-6-m-chlorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]
methyl-3,4-dihydroquinazolin-4-one 192.2-[exo-6-o-methoxyphenyl-3-azabicyclo[3.2.0]heptan-3-yl]-methyl-3,4-dihydroquinazolin-4-one 193.2-[exo-6-p-fluorophenyl-3-azabicyclo(3.2.0]heptan-3-yl]-methyl-4-hydroxy-6-methylpyrimidine 194.6-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl)-methyl-2-methyl-4-hydroxypyrimidine 195.6-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]-methyluracil 196.6-[exo-6-phenyl-3-azabicyclo[3.2.0]heptan-3-yl]methyl-uracil 197.6-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]-1,2,3,4-tetrahydro-1,3-dimethyl-2,4-dioxopyrimidine 198.5-~-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0)heptan-3-yl]ethyl-1,2,3,4-tetrahydro-6-methyl-2,4-dioxopyrimidine 199.5-~-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0)heptan-3-yl]-ethyl-1,2,3,4-tetrahydro-1,6-dimethyl-2,4-dioxopyrimidine 200.5-~-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]-ethyl-1,2,3,4-tetrahydro-3,6-dimethyl-2,4-dioxopyrimidine 201.5-~-[exo-6-p-fluorophenyl-3-azabicyclo(3.2.0]heptan-3-yl)-ethyl-1,2,3,4-tetrahydro-3,6-dimethyl-2,4-dithiopyrimidine 202.5-~-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0)heptan-3-yl]
ethyl-1,2,3,4-tetrahydro-1,3,6-trimethyl-2,4-dioxopyrimidine 203.5-~-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]-ethyl-1,2,3,4-tetrahydro-6-amino-1-methyl-2,4-dioxo-pyrimidine 204.5-~-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]-ethyl-2-amino-6-methyl-4(3H)pyrimidinone 205.5-~-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]-ethyl-2-amino-3,6-dimethyl-4(3H)pyrimidinone 206.5-13-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]-ethyl-2-methylamino-3,6-dimethyl-4(3H)pyrimidinone 207.5-J3-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]-ethyl-2-methylamino-3-ethyl-6-methyl-4(3H)pyrimidinone 208.5-!3-[exo-6-p-fluorophenyl-3-azabicyclo(3.2.0]heptan-3-yl]-ethyl-2-amino-3-ethyl-6-methyl-4(3H)pyrimidinone 209.5-J3-[exo-6-p-chlorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]
ethyl-2-methylamino-3,6-dimethyl-4(3H)pyrimidinone 210.5-13-[exo-6-m-chlorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]-ethyl-2-methylamino-3,6-dimethyl-4(3H)pyrimidinone 211.5-!3-[exo-6-o-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]-ethyl-2-methylamino-3,6-dimethyl-4(3H)pyrimidinone 212.5-13-[exo-6-p-trifluoromethylphenyl-3-azabicyclo[3.2.0]-heptan-3-yl]ethyl-2-methylamino-3,6-dimethyl-4(3H)-pyrimidinone 213.5-J3-[exo-6-p-cyanophenyl-3-azabicyclo[3.2.0]heptan-3-yl]ethyl-2-methylamino-3,6-dimethyl-4(3H)pyrimidinone 214.5-f3-[exo-6-m-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]ethyl-2-methylamino-3,6-dimethyl-4(3H)pyrimidinone 215.5-B-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]ethyl-2-methylamino-4-methoxy-6-methylpyrimidine 216.3-~-[exo-6-phenyl-7-methyl-1,5-cis-3,7-diazabic clo 3.3.0 -octan-3-yl]ethyl-2,4-(iH,3H)quinazolinedione 217.~3-~-[endo-6-phenyl-7-methyl-1,5-cis-3,7-diazabicyclo[3.3.0]-octan-3-yl]ethyl-2,4-(1H,3H)quinazolinedione 218.3-~-[exo-6-p-fluorophenyl-7-methyl-1,5-cis-3,7-diazabicyclo-[3.3.0]octan- 3-yl]ethyl-2,4-(1H,3H)quinazolinedione 219.3-~3-[exo-6-p-trifluoromethylphenyl-7-methyl-1,5-cis-3,7-diazabicyclo[3.3.0]octan-3-yl]ethyl-6-fluoro-2,4-(1H,3H)-quinazolinedione 220.3-~-[exo-6-m-chlorophenyl-7-methyl-1,5-cis-3,7-diazabicyclo-[3.3.0]octan-3-yl]ethyl-2,4-(1H,3H)quinazolinedione 221.3-~-[exo-6-p-methoxyphenyl-7-methyl-1,5-cis-3,7-diazabicyclo-[3.3.0]octan-3-yl]ethyl-6-methyl-2,4-(1H,3H)quinazolinedione 222.5-~-[exo-6-phenyl-7-methyl-1,5-cis-3,7-diazabicyclo[3.3.0]-5 octan-3-yl]ethyl-2-methylamino-3,6-dimethyl-4(3H)-pyrimidinone 223.5-~-[exo-6-p-fluorophenyl-7-methyl-1,5-cis-3,7-diazabicyclo-[3.3.0]octan-3-yl]ethyl-2-methylamino-3,6-dimethyl-10 4(3H)pyrimidinone 224.1-~-[exo-6-p-fluorophenyl-7-methyl-1,5-cis-3,7-diazabicyclo-[3.3.0]octan-3-yl]ethyl-2(3H)benzimidazolone 15 225.5-~-[exo-6-p-nitrophenyl-7-methyl-1,5-cis-3,7-diazabicyclo-[3.3.0]octan-3-yl]ethyl-2-methylamino-3,6-dimethyl-4(3H)pyrimidinone 226.5-~-[exo-6-phenyl-7-methyl-1,5-cis-3,7-diazabicyclo[3.3.0]-20 octan-3-yl]ethyl-2-methylamino-3,6-dimethyl-4(3H)-pyrimidinone 227.5-~-[endo-6-phenyl-7-methyl-1,5-cis-3,7-diazabicyclo[3.3.0]-octan-3-yl]ethyl-2-methylamino-3,6-dimethyl-4(3H)-pyrimidinone 228.3-~-[exo-6-p-fluorophenyl-7-methyl-1,5-cis-3,7-diazabicyclo-[3.3.0]octan-3-yl]ethyl-2-methyl-4H-pyrido[1.2-a]-pyrimidin-4-one 229.1-~-[exo-6-p-fluorophenyl-7-methyl-1,5-cis-3,7-diazabicyclo-[3.3.0]octan-3-yl]ethylindolin-2-one 230.6-~-[exo-6-p-fluorophenyl-7-methyl-1,5-cis-3,7-diazabicyclo-[3.3.0]octan-3-yl]ethyl-7-methyl-5H-thiazolo[3.2-a]-pyrimidin-5-one 231.I-~-[exo-6-p-fluorophenyl-7-methyl-1,5-cis-3,7-diazabicyclo-[3.3.0]octan-3-yl]ethyl-2(1H)quinolone 232.3-~-[7-phenyl-1,5-cis-3,7-diazabicyclo[3.3.0]octan-3-yl]-ethyl-2,4-(1H,3H)quinazolinedione 233.3-~-[7-p-fluorophenyl-1,5-cis-3,7-diazabicyclo[3.3.0]-octan-3-yl]ethyl-2,4-(1H,3H)quinazolinedione 234.5-~-[7-p-fluorophenyl-1,5-cis-3,7-diazabicyclo[3.3.0]-octan-3-yl]ethyl-2-methylamino-3,6-dimethyl-4(3H)pyrimidinone 235.3-~-[exo-6-p-fluorophenyl-3-azabicyclo[3.1.0]hexan-3-yl]-ethyl-2,4-(1H,3H)quinazolinedione 236.3-~-[exo-6-phenyl-3-azabicyclo[3.1.0]hexan-3-yl)ethyl-2,4-(1H,3H)quinazolinedione 237.3-~-[6,6-diphenyl-3-azabicyclo[3.1.0]hexan-3-yl]ethyl-2,4-(1H,3H)quinazolinedione 238.5-~-[exo-6-p-fluorophenyl-3-azabicyclo[3.1.0]hexan-3-yl)-ethyl-2-methylamino-3,6-dimethyl-4(3H)pyrimidinone 239.6-~-[exo-6-m-chlorophenyl-3-azabicyclo[3.1.0]hexan-3-yl]-ethyl-7-methyl-5H-thiazolo[3,2-a]pyrimidin-5-one 240.3-~-[6-p-fluorophenyl-1,5-cis-3-azabicyclo[3.3.0]oct-6-en-3-yl]ethyl-2,4-(1H,3H)quinazolinedione 241.5-~-[6-p-fluorophenyl-1,5-cis-3-azabicyclo[3.3.0)oct-6-en-3-yl)ethyl-2-methylamino-3,6-dimethyl-4(3H)pyrimidinone 242.6-~-[6-p-fluorophenyl-1,5-cis-3-azabicyclo[3.3.0]oct-6-en-3-yl]ethyl-7-methyl-5H-thiazolo[3,2-a)pyrimidin-5-one 243.1-~-[6-phenyl-1,5-cis-3-azabicyclo[3.3.0]oct-6-en-3-yl]-ethyl-2(3H)benzimidazolone 244.1-~-[6-p-fluorophenyl-1,5-cis-3-azabicyclo[3.3.0]oct-6-en-3-yl]ethylindolin-2-one 245.1-~-[6-p-fluorophenyl-1,5-cis-3-azabicyclo[3.3.0]oct-6-en-3-yl)ethyl-2(1H)quinolone 246.3-~-[exo-6-p-fluorophenyl-1,5-cis-3-azabicyclo[3.3.0]octan-3-yl)ethyl-2,4-(1H,3H)quinazolinedione 247.5-~-[exo-6-p-fluorophenyl-1,5-cis-3-azabicyclo[3.3.0]octan-3-yl]ethyl-2-methylamino-3,6-dimethyl-4(3H)pyrimidinone 248.6-~-[exo-6-phenyl-1,5-cis-3-azabicyclo[3.3.0]octan-3-yl]-ethyl-7-methyl-5H-thiazolo[3,2-a]pyrimidin-5-one 249.1-~-[exo-6-p-fluorophenyl-1,5-cis-3-azabicyclo[3.3.0]octan-3-yl]ethylindolin-2-one 250.1-~-[exo-6-p-fluorophenyl-1,5-cis-3-azabicyclo[3.3.0]octan-3-yl]ethyl-2(1H)quinolone 251.3-~-[endo-6-p-fluorophenyl-1,5-cis-3-azabicyclo[3.3.0]octan-3-yl]ethyl-2,4-(1H,3H)quinazolinedione 252.5-~-[endo-6-p-fluorophenyl-1,5-cis-3-azabicyclo[3.3.0]octan-3-yl]ethyl-2-methylamino-3,6-dimethyl-4(3H)pyrimidinone 253.6-~-[endophenyl-1,5-cis-3-azabicyclo[3.3.0]octan-3-yl]-ethyl-7-methyl-5H-thiazolo[3.2-a]pyrimidin-5-one 254.1-~-[endo-6-p-fluorophenyl-1,5-cis-3-azabicyclo[3.3.0]octan-3-yl]ethylindolin-2-one 255.1-~-[endo-6-p-fluorophenyl-1,5-cis-3-azabicyclo[3.3.0]octan-3-yl]ethyl-2(1H)quinolone 256.3-~-[exo-7-p-fluorophenyl-1,5-cis-3-azabicyclo[3.3.0]octan-3-yl]ethyl-2,4-(1H,3H)quinazolinedione 257.5-~-[exo-7-p-fluorophenyl-1,5-cis-3-azabicyclo[3.3.0]octan-3-yl]ethyl-2-methylamino-3,6-dimethyl-4(3H)pyrimidinone 258.6-~-[exo-7-phenyl-1,5-cis-3-azabicyclo[3.3.0]octan-3-yI]-ethyl-7-methyl-SH-thiazolo[3.2-a]pyrimidin-5-one 259.1-~-[exo-7-p-fluorophenyl-1,5-cis-3-azabicyclo[3.3.0]octan-3-yl]ethylindolin-2-one 260.1-~-[exo-7-p-fluorophenyl-1,5-cis-3-azabicyclo[3.3.0]octan-3-yl]ethyl-2(iH)quinolone 261.3-~-[endo-6-p-fluorophenyl-1,5-cis-3-azabicyclo[4.3.0]non-3-yl]ethyl-2,4-(1H,3H)quinazolinedione 262.5-~-[endo-6-p-fluorophenyl-1,5-cis-3-azabicyclo[4.3.0]non-3-yl]ethyl-2-methylamino-3,6-dimethyl-4(3H)pyrimidinone 263.3-~-[endo-6-phenyl-1,5-cis-3-azabicyclo[4.3.0]non-3-yl]-ethyl-2,4-(1H,3H)quinazolined~one 264.5-~-[endo-6-phenyl-1,5-cis-3-azabicyclo[4.3.0]non-3-yl]
ethyl-2-methylamino-3,6-dimethyl-4(3H)pyrimidinone 265.3-~-[endo-6-p-trifluoromethylphenyl-1,5-cis-3-azabicyclo-[4.3.0]non-3-yl]ethyl-2,4-(1H,3H)quinazolinedione, 266.5-/3-(endo-6-p-trifluoromethylphenyl-1,5-cis-3-azabicyclo-[4.3.0]non-3-yl]ethyl-2-methylamino-3,6-dimethyl-4(3H)-pyrimidinone 267.3-~-[endo-6-p-fluorophenyl-1,5-cis-3-azabicyclo[4.3.0]non-7-en-3-yl]ethyl-2,4-(1H,3H)quinazolinedione 268.5-~-(endo-6-p-fluorophenyl-1,5-cis-3-azabicyclo[4.3.0]non-7-en-3-yl]ethyl-2-methylamino-3,6-dimethyl-4(3H)-pyrimidinone 269.1-~-[endo-6-p-fluorophenyl-1,5-cis-3-azabicyclo[4.3.0]non-7-en-3-yl]ethyl-2(3H)benzimidazolone 270.1-~-[endo-6-p-fluorophenyl-1,5-cis-3-azabicyclo[4.3.0]non-7-en-3-yl]ethylindolin-2-one 271.3-~-[6-p-fluorophenyl-1,5-cis-3-azabicyclo[4.3.0]non-6-en-3-yl]ethyl-2,4-(1H,3H)quinazolinedione 272.5-~-[6-p-fluorophenyl-1,5-cis-3-azabicyclo[4.3.0]non-6-en 3-yl]ethyl-2-methylamino-3,6-dimethyl-4(3H)pyrimidinone 273.3-~-[6-phenyl-1,5-cis-3-azabicyclo[4.3.0]non-6-en-3-yl]-ethyl-2,4-(1H,3H)quinazolinedione 274.5-~-[6-phenyl-1,5-cis-3-azabicyclo[4.3.0]non-6-en-3-yl]-ethyl-2-methylamino-3,6-dimethyl-4(3H)pyrimidinone 275.3-~-[6-p-trifluoromethylphenyl-1,5-cis-3-azabicyclo-[4.3.0]non-6-en-3-yl]ethyl-2,4-(1H,3H)quinazolinedione 276.5-~-[6-p-trifluoromethylphenyl-1,5-cis-3-azabicyclo[4.3.0]-non-6-en-3-yl]ethyl-2-methylamino-3,6-dimethyl-4(3H)-pyrimidinone 277.1-~-[6-p-fluorophenyl-1,5-cis-3-azabicyclo[4.3.0]non-6-en-3-yl]ethyl-2(3H)benzimidazolone 278.1-~-[6-p-fluorophenyl-1,5-cis-3-azabicyclo[4.3.0]non-6-en-3-yl]ethylindolin-2-one 279.1-~-[6-p-fluorophenyl-1,5-cis-3-azabicyclo[4.3.0]non-6-en-3-yl]ethyl-2(1H)quinolone 280.3-~-[exo-6-p-fluorophenyl-1,5-cis-3-azabicyclo[4.3.0]non-7-en-3-yl]ethyl-2,4-(1H,3H)quinazolidone 281.5-~-[exo-6-p-fluorophenyl-1,5-cis-3-azabicyclo[4.3.0]non-7-en-3-yl]ethyl-2-methylamino-3,6-dimethyl-4(3H)pyrimidinone 282.3-~-[exo-6-p-fluorophenyl-1,5-cis-3-azabicyclo[4.3.0]non-7-en-3-yl]ethyl-2-methyl-4H-pyrido[1.2-a]pyrimidin-4-one 283.1-~-[exo-6-p-fluorophenyl-1,5-cis-3-azabicyclo[4.3.0]non-7-en-3-yl]ethyl-2(1H)quinolone 284.1-~-[exo-6-p-fluorophenyl-1,5-cis-3-azabicyclo[4.3.0]non-7-en-3-yl]ethyl-2(3H)benzimidazolone 285.1-~-[exo-6-p-fluorophenyl-1,5-cis-3-azabicyclo[4.3.0]non-7-en-3-yl]ethylindolin-2-one 286.3-~-[exo-6-phenyl-1,5-cis-3-azabicyclo[4.3.0]non-7-en-3-yl]-ethyl-2,4-(1H,3H)quinazolinedione 287.5-~-[exo-6-phenyl-1,5-cis-3-azabicyclo[4.3.0]non-7-en-3-yl]-ethyl-2-methylamino-3,6-dimethyl-4(3H)pyrimidinone 288.3-~-[exo-6-p-fluorophenyl-1,5-cis-3-azabicyclo[4.3.0]non-3-yl]ethyl-2,4-(1H,3H)quinazolinedione 289.5-~-[exo-6-p-fluorophenyl-1,5-cis-3-azabicyclo[4.3.0]non-3-yl]ethyl-2-methylamino-3,6-dimethyl-4(3H)pyrimidinone 290.3-~-[exo-6-phenyl-1,5-cis-3-azabicyclo[4.3.0)non-3-yl]ethyl-2,4-(1H,3H)quinazolinedione 291.5-~-[exo-6-phenyl-1,5-cis-3-azabicyclo[4.3.0]non-3-yl]ethyl-2-methylamino-3,6-dimethyl-4(3H)pyrimidinone 292.6-~-[exo-6-p-fluorophenyl-1,5-cis-3-azabicyclo[4.3.0]non 3-yl]ethyl-7-methyl-5H-thiazQlo[3.2-a]pyrimidin-5-one 0050/49558 ~ 02352526 2001-05-23 293.1-~-[exo-6-p-fluorophenyl-1,5-cis-3-azabicyclo[4.3.0)non-3-yl)ethyl-2(3H)benzimidazolone 294.1-~-[exo-6-p-fluorophenyl-1,5-cis-3-azabicyclo[4.3.0)non-5 3-yl]ethylindolin-2-one 295.1-~-[exo-6-p-fluorophenyl-1,5-cis-3-azabicyclo[4.3.0]non-3-yl]ethyl-2(1H)quinolone 10 296.3-~-[exo-7-phenyl-1,5-cis-3-azabicyclo[4.3.0]non-8-en-3-yl]-ethyl-2,4-(1H,3H)quinazolinedione 297.5-~-[exo-7-phenyl-1,5-cis-3-azabicyclo[4.3.0)non-8-en-3-yl]-ethyl-2-methylamino-3,6-dimethyl-4(3H)pyrimidinone 298.3-~-[exo-7-p-fluorophenyl-1,5-cis-3-azabicyclo[4.3.0]non-8-en-3-yl]ethyl-2,4-(1H,3H)quinazolinedione 299.5-~-[exo-7-p-fluorophenyl-1,5-cis-3-azabicyclo[4.3.0)non-8-en-3-yl]ethyl-2-methylamino-3,6-dimethyl-4(3H)-pyrimidinone 300.3-~-[7-p-fluorophenyl-3-azabicyclo[4.3.0]non-1-en-3-yl]-ethyl-2,4-(1H,3H)quinazolinedione 301.5-~-[7-phenyl-3-azabicyclo[4.3.0]non-1-en-3-yl]ethyl-2-methylamino-3,6-dimethyl-4(3H)pyrimidinone 302.5-~-[7-p-fluorophenyl-3-azabicyclo[4.3.0)non-1-en-3-yl)-ethyl-2-methylamino-3,6-dimethyl-4(3H)pyrimidinone 303.3-~-[exo-7-p-fluorophenyl-1,5-cis-3-azabicyclo[4.3.0]non-3-yl]ethyl-2,4-(1H,3H)quinazolinedione 304.5-~-[exo-7-p-fluorophenyl-1,5-cis-3-azabicyclo[4.3.0]non-3-yl]ethyl-2-methylamino-3,6-dimethyl-4(3H)pyrimidinone 305.1-~-[exo-7-p-fluorophenyl-1,5-cis-3-azabicyclo[4.3.0]non-3-yl]ethyl-2(3H)benzimidazolone 306.1-~-[exo-7-p-fluorophenyl-1,5-cis-3-azabicyclo[4.3.0]non-3-yl]ethylindolin-2-one 307.1-~-[exo-7-p-fluorophenyl-1,5-cis-3-azabicyclo[4.3.0]non-3-yl]ethyl-2(1H)quinolone 0050/49558 ~ 02352526 2001-05-23 308.3-~-[6-p-fluorophenyl-1,5-cis-8-oxa-3,7-diazabicyclo[3.3.0]-oct-6-en-3-yl]ethyl-2,4-(1H,3H)quinazolinedione 309.5-~-[6-p-fluorophenyl-1,5-cis-8-oxa-3,?-diazabicyclo[3.3.0]-oct-6-en-3-yl]ethyl-2-methylamino-3,6-dimethyl-4(3H)-pyrimidinone 310.3-~-[exo/endo-6-p-fluorophenyl-1,5-cis-8-oxa-3,7-diaza-bicyclo[3.3.0j-octan-3-yljethyl-2,4-(1H,3H)quinazolinedione 311.5-~-[exo/endo-6-p-fluorophenyl-1,5-cis-8-oxa-3,7-diaza-bicyclo[3.3.0]octan-3-yl]ethyl-2-methylamino-3,6-dimethyl-4(3H)pyrimidinone 312.1-~-[6-p-fluorophenyl-1,5-cis-8-oxa-3,7-diazabicyclo[3.3.0]-oct-6-en-3-yl]ethylindolin-2-one 313.6-~-[6-phenyl-1,5-cis-8-oxa-3,7-diazabicyclo[3.3.Oj-oct-6-en-3-yl]ethyl-7-methyl-5H-thiazolo[3,2-a]pyrimidin-5-one 314.N-(2-[exo-6-phenyl-7-methyl-1,5-cis-3,7-diazabicyclo[3.3.0]-octan-3-yl]ethyl)-4-fluorobenzamide 315.N-(2-[endo-6-phenyl-7-methyl-1,5-cis-3,?-diazabicyclo[3.3.0]-octan-3-yl]ethyl)-4-fluorobenzamide 316.N-(2-(exo-6-p-fluorophenyl-7-methyl-1,5-cis-3,7-diazabicyclo-[3.3.0]octan-3-yljethyl)-4-fluorobenzamide 317.N-(2-[exo-6-p-trifluoromethylphenyl-7-methyl-1,5-cis-3,7-diazabicyclo[3.3.0]octan-3-yl]ethyl)benzamide 318.N-(2-[exo-6-m-chlorophenyl-7-methyl-1,5-cis-3,7-diazabicyclo-[3.3.0]octan-3-yljethyl)benzamide 319.N-(2-[exo-6-p-methoxyphenyl-7-methyl-1,5-cis-3,7-diaza-bicyclo[3.3.0]octan-3-yl]ethyl)-4-chlorobenzamide 320.N-(2-[exo-6-phenyl-7-methyl-1,5-cis-3,7-diazabicyclo[3.3.0]-octan-3-yl]ethyl)naphthalene-1-carboxamide 321.1-(4-fluorophenyl)-4-[exo-6-p-fluorophenyl-7-methyl-1,5-cis-3,7-diazabicyclo[3.3.Ojoc.tan-3-yljbutan-1-one 0050/49558 ~ 02352526 2001-05-23 322.1-(4-fluorophenyl)-4-[exo-6-p-fluorophenyl-7-methyl-1,5-cis-3,7-diazabicyclo[3.3.0]octan-3-yl]butan-1-of 323.N-(2-[exo-6-p-fluorophenyl-1,5-cis-3-azabicyclo[4.3.0]-non-3-yl]ethyl)benzamide 324.1-(2-[exo-6-p-fluorophenyl-1,5-cis-3-azabicyclo[4.3.0]-non-3-yl]ethyl)naphthalene 325.1-(4-fluorophenyl)-4-[exo-6-p-fluorophenyl-1,5-cis-3-azabicyclo[4.3.0]non-3-yl]butan-1-one 326.1-(4-fluorophenyl)-4-[exo-6-p-fluorophenyl-1,5-cis-3-azabicyclo[4.3.0]non-3-yl]butan-1-of 327.N-(2-[exo-6-p-fluorophenyl-1,5-cis-3-azabicyclo[4.3.0]non-3-yl]ethyl)-2-(N-methyl)aminobenzamide 328.N-(2-[exo-6-p-fluorophenyl-1,5-cis-3-azabicyclo[4.3.0]non-3-yl]ethyl)-5-chlorothien-2-ylcarboxamide 329.N-(2-[exo-6-p-fluorophenyl-1,5-cis-3-azabicyclo[4.3.0]non-3-yl]ethyl)indene-3-carboxamide 330.N-(2-[exo-6-phenyl-1,5-cis-3-azabicyclo[4.3.0]non-3-yl]-ethyl)-4-fluorobenzamide 331.N-(2-[exo-6-phenyl-1,5-cis-3-azabicyclo[4.3.0]non-3-yl]-ethyl)naphthalene-1-carboxamide 332.1-(2-[exo-6-p-fluorophenyl-1,5-cis-3-azabicyclo[4.3.0]non-7-en-3-yl]ethyl)naphthalene 333.1-(4-fluorophenyl)-4-[exo-6-p-fluorophenyl-1,5-cis-3-aza-bicyclo[4.3.0]non-7-en-3-yl]butan-1-one 334.N-(2-[exo-6-p-fluorophenyl-1,5-cis-3-azabicyclo[4.3.0]non-7-en-3-yl]ethyl)benzamide 335.N-(2-[exo-6-p-fluorophenyl-1,5-cis-3-azabicyclo[4.3.0]non-7-en-3-yl]ethyl)indene-3-carboxamide 336.N-(2-[exo-6-p-fluorophenyl-1,5-cis-3-azabicyclo[4.3.0]non-7-en-3-yl]ethyl)naphthalene-1-carboxamide 0050/49558 ~ 02352526 2001-05-23 337.N-(2-(exo-6-phenyl-1,5-cis-3-azabicyclo[4.3.0]non-7-en-3-yl]-ethyl)-4-fluorobenzamide 338.N-(2-[exo-6-phenyl-1,5-cis-3-azabicyclo[4.3.0]non-7-en-3-yl]-ethyl)-3-chloro-1-benzothien-2-ylcarboxamide 339.1-(2-[6-p-fluorophenyl-1,5-cis-3-azabicyclo[4.3.0]non-6-en-3-yl]ethyl)naphthalene 340.1-(4-fluorophenyl)-4-[6-p-fluorophenyl-1,5-cis-3-azabicyclo-[4.3.0]non-6-en-3-yl]butan-1-one 341.1-(4-fluorophenyl)-4-[6-p-fluorophenyl-I,5-cis-3-azabicyclo-[4.3.0]non-6-en-3-yl]butan-1-of 342.N-(2-[6-p-fluorophenyl-1,5-cis-3-azabicyclo[4.3.0]non-6-en-3-yl]ethyl)-2-(N-methyl)aminobenzamide 343.N-(2-[6-p-fluorophenyl-1,5-cis-3-azabicyclo[4.3.0]non-6-en-3-yl]ethyl)-5-chlorothien-2-ylcarboxamide 344.N-(2-[6-p-fluorophenyl-1,5-cis-3-azabicyclo[4.3.0]non-6-en-3-yl]ethyl)benzamide 345.N-(2-[6-phenyl-1,5-cis-3-azabicyclo[4.3.0]non-6-en-3-yl]-ethyl)-3-chloro-1-benzothien-2-ylcarboxamide 346.N-(2-[6-p-trifluoromethylphenyl-1,5-cis-3-azabicyclo[4.3.0]-non-6-en-3-yl]ethyl)naphthalene-1-carboxamide 347.N-(2-(6-p-fluorophenyl-1,5-cis-3-azabicyclo[4.3.0]non-6-en-3-yl]ethyl)indene-3-carbonimide 348.N-(2-[6-p-fluorophenyl-1,5-cis-3-azabicyclo[4.3.0]non-6-en-3-yl]ethyl)napthalene-1-carboxamide 349.1-(2-[endo-6-p-fluorophenyl-1,5-cis-3-azabicyclo[4.3.0]non-3-yl]ethyl)naphthalene 350.1-(4-fluorophenyl)-4-[endo-6-p-fluorophenyl-1,5-cis-3-azabicyclo[4.3.0]non-3-yl]butan-1-one 351.1-(4-fluorophenyl)-4-(endo-6-p-fluorophenyl-1,5-cis-3-azabicyclo[4.3.0]non-3-yl]butan-1-of 352.N-(2-[endo-6-p-fluorophenyl-1,5-cis-3-azabicyclo[4.3.0]non-3-ylj-2-(N-methyl)aminobenzamide 353.N-(2-[endo-6-p-fluorophenyl-1,5-cis-3-azabicyclo[4.3.0]non-3-yl]ethyl)benzamide 354.N-(2-[endo-6-p-fluorophenyl-1,5-cis-3-azabicyclo[4.3.0]non-3-yljethyl)-5-chlorothien-2-ylcarboxamide 355.N-(2-[endo-6-phenyl-1,5-cis-3-azabicyclo[4.3.0]non-3-yl]-ethyl)-4-fluorobenzamide 356.N-(2-[endo-6-p-trifluoromethylphenyl-1,5-cis-3-azabicyclo-[4.3.0]non-3-yl]ethyl)indene-3-carboxamide 357.2-(2-[endo-6-p-fluorophenyl-1,5-cis-3-azabicyclo[4.3.Ojnon-7-en-3-yl]ethyl)naphthalene 358.N-(2-[endo-6-p-fluorophenyl-1,5-cis-3-azabicyclo[4.3.0]non-7-en-3-yl]ethyl)benzamide 359.N-(2-[endo-6-p-fluorophenyl-1,5-cis-3-azabicyclo[4.3.0]non-7-en-3-yljethyl)-2-(N-methyl)aminobenzamide 360.N-(2-[endo-6-p-fluorophenyl-1,5-cis-3-azabicyclo[4.3.Ojnon-7-en-3-yl]ethyl)naphthalene-1-carboxamide 361.1-(2-[exo-7-p-fluorophenyl-1,5-cis-3-azabicyclo[4.3.Ojnon-8-en-3-yl]ethyl)naphthalene 362.1-(4-fluorophenyl)-4-[exo-7-p-fluorophenyl-1,5-cis-3-azabicyclo[4.3.0]non-8-en-3-yl]butan-1-one 363.N-(2-[exo-7-p-fluorophenyl-1,5-cis-3-azabicyclo[4.3.0]non-8-en-3-yl]ethyl)benzamide 364.N-(2-[exo-7-p-fluorophenyl-1,5-cis-3-azabicyclo[4.3.0]non-8-en-3-yl]ethyl)-5-chlorothien-2-ylcarboxamide 365.N-(2-[exo-7-p-fluorophenyl-1,5-cis-3-azabicyclo[4.3.0]non-8-en-3-yl]ethyl)-3-chloro-1-benzothien-2-ylcarboxamide 366.N-(2-[exo-7-phenyl-1,5-cis-3-azabicyclo[4.3.0]non-8-en-3-yl]ethyl)indene-3-carboxamide 367.N-(2-[exo-7-phenyl-1,5-cis-3-azabicyclo(4.3.0]non-8-en-3-yl]ethyl)naphthalene-1-carboxamide 368.1-(2-[exo-7-p-fluorophenyl-1,5-cis-3-azabicyclo[4.3.0]non-5 3-yl]ethyl)naphthalene 369.1-(4-fluorophenyl)-4-[exo-7-p-fluorophenyl-1,5-cis-3-azabicyclo[4.3.0]non-3-yl]butan-1-one 10 370.1-(4-fluorophenyl)-4-[exo-7-p-fluorophenyl-1,5-cis-3-azabicyclo[4.3.0]non-3-yl]butan-1-of 371.N-(2-[exo-7-p-fluorophenyl-1,5-cis-3-azabicyclo[4.3.0]non-3-yl]ethyl)-2-(N-methyl)aminobenzamide 372.N-(2-[exo-7-p-fluorophenyl-1,5-cis-3-azabicyclo[4.3.0]non-3-yl]ethyl)benzamide 373.N-(2-[exo-7-p-fluorophenyl-1,5-cis-3-azabicyclo[4.3.0]non-3-yl]ethyl)-5-chlorothien-2-ylcarboxamide 374.N-(2-[exo-7-p-fluorophenyl-1,5-cis-3-azabicyclo[4.3.0]non-3-yl]ethyl)naphthalene-1-carboxamide 375.N-(2-[exo-7-p-fluorophenyl-1,5-cis-3-azabicyclo[4.3.0]non-3-yl]ethyl)indene-3-carboxamide 376.1-(2-[6-p-fluorophenyl-1,5-cis-3-azabicyclo[3.3.0]oct-6-en-3-yl]ethyl)naphthalene 377.1-(4-fluorophenyl)-4-[6-p-fluorophenyl-1,5-cis-3-azabicyclo-[3.3.0]oct-6-en-3-yl]butan-1-one 378.N-(2-[6-p-fluorophenyl-1,5-cis-3-azabicyclo[3.3.0]oct-6-en-3-yl]ethyl)benzamide, 379.N-(2-[6-p-fluorophenyl-1,5-cis-3-azabicyclo[3.3.0]oct-6-en-3-yl]ethyl)naphthalene-1-carboxamide 380.1-(2-[exo-6-p-fluorophenyl-1,5-cis-3-azabicyclo[3.3.0]octan-3-yl]ethyl)naphthalene 381.1-(4-fluorophenyl)-4-[exo-6-p-fluorophenyl-1,5-cis-3-azabicyclo-(3.3.0]octan-3-yl]butan-1-of 0050/49558 ~ 02352526 2001-05-23 382.N-(2-[exo-6-p-fluorophenyl-1,5-cis-3-azabicyclo[3.3.0]octan-3-yl]ethyl)benzamide 383.N-(2-[exo-6-phenyl-1,5-cis-3-azabicyclo[3.3.0]octan-3-yl]-ethyl)naphthalene-1-carboxamide 384.N-(2-[exo-6-phenyl-1,5-cis-3-azabicyclo[3.3.0]octan-3-yl]-ethyl)indene-3-carboxamide 385.1-(2-[endo-6-p-fluorophenyl-1,5-cis-3-azabicyclo[3.3.0]octan-3-yl]ethyl)naphthalene 386.1-(4-fluorophenyl)-4-[endo-6-p-fluorophenyl-1,5-cis-3-azabicyclo[3.3.0]octan-3-yl]butan-1-one 387.N-(2-[endo-6-p-fluorophenyl-1,5-cis-3-azabicyclo[3.3.0]octan-3-yl]ethyl)benzamide 388.N-(2-[endo-6-phenyl-1,5-cis-3-azabicyclo[3.3.0]octan-3-yl]-ethyl)naphthalene-1-carboxamide 389.1-(2-[exo-7-p-fluorophenyl-1,5-cis-3-azabicyclo[3.3.0]octan-3-yl]ethyl)naphthalene 390.1-(4-fluorophenyl)-4-[exo-7-p-fluorophenyl-1,5-cis-3-azabicyclo[3.3.0]octan-3-yl]butan-1-one 391.N-(2-[exo-7-p-fluorophenyl-1,5-cis-3-azabicyclo[3.3.0]octan-3-yl]ethyl)benzamide 392.N-(2-[exo-7-phenyl-1,5-cis-3-azabicyclo[3.3.0]octan-3-yl]-ethyl)naphthalene-1-carboxamide 393.N-(2-[exo-7-phenyl-1,5-cis-3-azabicyclo[3.3.0]octan-3-yl]-ethyl)indene-3-carboxamide 394.N-(2-[exo-6-p-fluorophenyl-3-azabicyclo[3.1.0]hexan-3-yl]-ethyl)-4-fluorobenzamide 395.N-(2-[exo-6-phenyl-3-azabicyclo[3.1.0]hexan-3-yl]ethyl)-5-chlorothien-2-ylcarboxamide 396.N-(2-[6,6-diphenyl-3-azabicyclo[3.1.0]hexan-3-yl]ethyl)-naphth-1-ylcarboxamide .

0050/49558 ~ 02352526 2001-05-23 397.N-(2-[exo-6-p-fluorophenyl-3-azabicyclo[3.1.0]hexan-3-yl]-ethyl)-3-chloro-1-benzothien-2-ylcarboxamide 398.N-(2-[exo-6-m-chlorophenyl-3-azabicyclo[3.1.0]hexan-3-yl]-ethyl)-4-chlorobenzamide 399.1-(2-[6-p-fluorophenyl-1,5-cis-8-oxa-3,7-diazabicyclo[3.3.0]-oct-6-en-3-yl]ethyl)naphthalene 400.N-(2-[6-p-fluorophenyl-1,5-cis-8-oxa-3,7-diazabicyclo[3.3.0]-oct-6-en-3-yl]ethyl)benzamide 401.N-(2-[6-p-fluorophenyl-1,5-cis-8-oxa-3,7-diazabicyclo[3.3.0]-oct-6-en-3-yl]ethyl)naphthalene-1-carboxamide 402.N-(2-[6-p-fluorophenyl-1,5-cis-8-oxa-3,7-diazabicyclo[3.3.0]-oct-6-en-3-yl]ethyl)indene-3-carboxamide 403.1-(2-[exo/endo-6-p-fluorophenyl-1,5-cis-8-oxa-3,7-diaza-bicyclo[3.3.0]octan-3-yl]ethyl)naphthalene 404.N-(2-[exo/endo-6-p-fluorophenyl-1,5-cis-8-oxa-3,7-diaza-bicyclo[3.3.0]octan-3-yl]ethyl)benzamide 405.1-(2-[6-phenyl-1-5-cis-8-oxa-3,7-diazabicyclo[3.3.0]oct-6-en-3-yl]ethyl)naphthalene 406.N-(2-[6-phenyl-1-5-cis-8-oxa-3,7-diazabicyclo[3.3.0]oct-6-en-3-yl]ethyl)benzamide 407.N-(2-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]-ethyl)benzosulfonamide 408.N-(2-[exo-6-phenyl-3-azabicyclo[3.2.0]heptan-3-yl]ethyl)-benzosulfonamide 409.N-(2-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]ethyl)-N-methylbenzosulfonamide 410.N-(2-[exo-6-(5-chlorothien-2-yl)-3-azabicyclo[3.2.0]heptan-3-yl]ethyl)-4-fluorobenzosulfonamide 411.3-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]-1-phenoxypropane .

0050/49558 ~ 02352526 2001-05-23 412.2-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl)-1-p-fluorophenoxyethane 413.3-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]-1-(1-naphthyloxy)propane 414.3-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]-1-p-t-butylphenoxypropane 415.3-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]-1-p-fluorophenoxypropane 416.N-(2-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl)ethyl)thiobenzamide 417.N-(2-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]-ethyl)-4-fluorothiobenzamide 418.N-(2-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]-ethyl)-4-chlorothiobenzamide 419.0-(2-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]-ethyl)benzoate 420.0-(2-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]-ethyl-4-fluorobenzoate 421.N-(2-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]
ethyl)-1H-benzo[cd]indol-2-one 422.N-(2-[exo-6-p-chlorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]-ethyl)-1H-benzo[cd]indol-2-one 423.N-(2-[exo-6-m-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]-ethyl)-1H-benzo[cd]indol-2-one 424.N-(2-[exo-6-m-chlorophenyl-3-azabicyclo[3.2.0)heptan-3-yl]-ethyl)-1H-benzo[cd]indol-2-one 425.3,3-dimethyl-1-(2-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]-heptan-3-yl]ethyl)indolin-2-one 426.3,3-dimethyl-1-(2-(exo-6-p-chlorophenyl-3-azabicyclo[3.2.0)-heptan-3-yl]ethyl)indolin-2-Qne 005049558 ~ 02352526 2001-05-23 427.3,3-dimethyl-1-(2-[exo-6-m-chlorophenyl-3-azabicyclo[3.2.0]-heptan-3-yl]ethyl)indolin-2-one 428.1-(2-[exo-6-p-chlorophenyl-3-azabicyclo[3.2.Ojheptan-3-yl]-ethyl)-3,3,5-trimethylindolin-2-one 429.3,4-dichloro-N-(2-[exo-6-p-nitrophenyl-3-azabicyclo[3.2.0]-heptan-3-yl]ethyl)benzamide 430.2,5-difluoro-N-(2-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]-heptan-3-yl]ethyl)benzamide 431.2-amino-N-(2-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]-heptan-3-yl]ethyl)benzamide 432.2-amino-N-(2-[exo-6-p-chlorophenyl-3-azabicyclo[3.2.0]-heptan-3-yl]ethyl)benzamide 433.N-(2-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0jheptan-3-yl]-ethyl)-2-methylaminobenzamide 434.N-(2-[exo-6-p-chlorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]-ethyl)-2-methylaminobenzamide 435.3-amino-N-(2-[exo-6-p-chlorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]ethyl)benzamide 436.4-amino-N-(2-[exo-6-p-chlorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]ethyl)benzamide 437.N-(2-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.Ojheptan-3-yl]-ethyl)thiophene-2-carboxamide 438.5-chloro-N-(2-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]-heptan-3-yl]ethyl)thiophene-2-carboxamide 439.5-chloro-N-(2-[exo-6-p-chlorophenyl-3-azabicyclo[3.2.0]-heptan-3-yl]ethyl)thiophene-2-carboxamide 440.5-chloro-N-(2-[exo-6-(5-chloro-2-thienyl)-3-azabicyclo [3.2.Ojheptan-3-yl]ethyl)thiophene-2-carboxamide 441.N-(2-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]-ethyl)benzo[b]furan-2-carboxamide 005/49558 ~ 02352526 2001-05-23 442.3-chloro-N-(2-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]-heptan-3-yl]ethyl)benzo[b]thiophene-2-carboxamide 443.3-chloro-N-(2-[exo-6-p-chlorophenyl-3-azabicyclo[3.2.0]-5 heptan-3-yl]ethyl)benzo[b]thiophene-2-carboxamide 444.3-chloro-N-(2-[exo-6-p-nitrophenyl-3 -azabicyclo[3.2.0]-heptan-3-yl]ethyl)benzo[b]thiophene-2-carboxamide 10 445.N-(2-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]-ethyl)indene-3-carboxamide 446.N-(2-[exo-6-p-chlorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]-ethyl)indene-3-carboxamide 447.N-(2-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]-ethyl)cyclopropanecarboxamide 448.N-(2-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]-ethyl)cyclopentanecarboxamide 449.N-(2-[exo-6-p-chlorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]-ethyl)cyclopentanecarboxamide 450.N-(2-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]-ethyl)cyclohexanecarboxamide 451.N-(2-[exo-6-p-chlorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]-ethyl)cyclohexanecarboxamide _ 30 452.N-(2-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]-ethyl)naphthalene-1-carboxamide 453.N-(2-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]-ethyl)indole-2-carboxamide 454.N-(2-[exo-6-p-chlorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]-ethyl)indole-3-carboxamide 455.exo-6-p-fluorophenyl-3-[2-(1-naphthyl)ethyl]-3-azabicyclo-[3.2.0]heptane 456.exo-6-p-chlorophenyl-3-[2-(1-naphthyl)ethyl]-3-azabicyclo-[3.2.0]heptane .

457.exo-6-m-chlorophenyl-3-[2-(1-naphthyl)ethyl]-3-azabicyclo-[3.2.0]heptane 458.exo-6-(5-chloro-2-thienyl)-3-[2-(1-naphthyl)ethyl]-3-azabicyclo[3.2.0]heptane 459.exo-6-p-fluorophenyl-3-[2-(2-naphthyl)ethyl]-3-azabicyclo-[3.2.0]heptane 460.exo-6-p-fluorophenyl-3-[1-naphthylmethyl]-3-azabicyclo-[3.2.0]heptane 461.exo-6-p-fluorophenyl-3-[2-naphthylmethyl]-3-azabicyclo-[3.2.0]heptane 462.4-(6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl)-1-(thio-phen-2-yl)butan-1-one 463.4-(6-p-chlorophenyl-3-azabicyclo[3.2.0]heptan-3-yl)-1-(thio-phen-2-yl)butan-1-one 464.N-(2-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]-ethyl)-4-phenylpyrrolidin-2-one 465.N-(2-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]-ethyl)benzoxazolin-2-one 466.N-(2-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]-ethyl)isoindolinone 467.1-(2-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]-ethyl)indazole 468.1-(2-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]-ethyl)-1,8-naphthalenesultam 469.4-(2-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]-ethyl)-1,4-benzoxazin-3-one 470.1-(2-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]-ethyl)quinoxalin-2(1H)-one 471.1-(2-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]-ethyl)indolin-2-one 0050/49558 ~ 02352526 2001-05-23 472.1-(2-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl]-ethyl)spiro[cyclopropane-1',3-indolin-2-one]
473.3,6-dimethyl-2-methylamino-5-[2-(exo-6-(2-naphthyl)-3-aza-bicyclo[3.2.0]heptan-3-yl)ethyl]-3H-pyrimidin-4-one 474.3,6-dimethyl-2-methylamino-5-[2-(exo-6-(1-naphthyl)-3-aza-bicyclo[3.2.0]heptan-3-yl)ethyl]-3H-pyrimidin-4-one 475.3,6-dimethyl-2-methylamino-5-[2-(exo-6-(5-chloro-1-naphthyl)-3-azabicyclo[3.2.0]heptan-3-yl)ethyl]-3H-pyrimidin-4-one 476.3,6-dimethyl-2-methylamino-5-[2-(exo-6-(6-chloro-2-naphthyl)-3-azabicyclo[3.2.0]heptan-3-yl)ethyl]-3H-pyrimidin-4-one 477.3,6-dimethyl-2-methylamino-5-[2-(exo-6-(9-phenanthryl)-3 azabicyclo[3.2.0]heptan-3-yl)ethyl]-3H-pyrimidin-4-one 478.7-methyl-6-[2-(exo-6-(2-naphthyl)-3-azabicyclo[3.2.0]heptan-3-yl)ethyl)-5H-thiazolo[3,2-a]pyrimidin-5-one 479.3-[2-(exo-6-(2-naphthyl)-3-azabicyclo[3.2.0]heptan-3-yl)-ethyl]-1H,3H-quinazoline-2,4-dione 480.3-[2-(exo-6-(1-naphthyl)-3-azabicyclo[3.2.0]heptan-3-yl)-ethyl]-1H,3H-quinazoline-2,4-dione 481.6-fluoro-3-[2-(exo-6-(1-naphthyl)-3-azabicyclo[3.2.0]heptan-3-yl)ethyl]-1H,3H-quinazoline-2,4-dione 482.3-[2-(exo-6-(5-chloro-2-naphthyl)-3-azabicyclo[3.2.0]heptan-3-yl)ethyl]-1H,3H-quinazoline-2,4-dione 483.3-[2-(exo-6-(1-naphthyl)-3-azabicyclo[3.2.0]heptan-3-yl)-ethyl]-2-methyl-4H-pyrido[1.2-a]pyrimidin-4-one 484.1-[2-(exo-6-(2-naphthyl)-3-azabicyclo[3.2.0]heptan-3-yl)-ethyl]-2(1H)quinolone 485.1-[2-(exo-6-(2-naphthyl)-3-azabicyclo[3.2.0]heptan-3-yl)-ethyl]indolin-2-one 486.1-[2-(exo-6-(1-naphthyl)-3-a2abicyclo[3.2.0]heptan-3-yl)-ethyl]-2(3H)benzimidazolone 0050/49558 ~ 02352526 2001-05-23 487.1-[2-(exo-6-(1-naphthyl)-3-azabicyclo[3.2.0]heptan-3-yl)-ethyl]-3-methyl-2(3H)benzimidazolone 488.N-[2-(exo-6-(1-naphthyl)-3-azabicyclo[3.2.0]heptan-3-yl)-ethyl]benzamide 489.N-[2-(exo-6-(2-naphthyl)-3-azabicyclo[3.2.0]heptan-3-yl)-ethyl]benzamide 490.N-[2-(exo-6-(5-chloro-1-naphthyl)-3-azabicyclo[3.2.0]-heptan-3-yl)ethyl]benzamide 491.3-[2-(1-naphthyl)ethyl]-exo-6-(1-naphthyl)-3-azabicyclo-[3.2.0]heptane 492.3-[2-(1-naphthyl)ethyl]-exo-6-(2-naphthyl)-3-azabicyclo-[3.2.0]heptane 493.1-[2-(exo-6-(1-naphthyl)-3-azabicyclo[3.2.0]heptan-3-yl)-ethyl]-1H-benzo[cd]indol-2-one 494.1-[2-(exo-6-(2-naphthyl)-3-azabicyclo[3.2.0]heptan-3-yl)-ethyl]-1H-benzo[cd]indol-2-one 495.3,3-dimethyl-1-[2-(exo-6-(1-naphthyl)-3-azabicyclo[3.2.0]-heptan-3-yl)ethyl]-1,3-dihydroindol-2-one 496.3,3-dimethyl-1-[2-(exo-6-(2-naphthyl)-3-azabicyclo-[3.2.0]heptan-3-yl)ethyl]-1,3-dihydroindol-2-one ,~ 497.3,3-dimethyl-1-[2-(exo-6-(6-chloro-2-naphthyl)-3-azabicyclo-[3.2.0]heptan-3-yl)ethyl]-1,3-dihydroindol-2-one 498.5-chloro-N-[2-(exo-6-(1-naphthyl)-3-azabicyclo[3.2.0]-heptan-3-yl)ethyl]-2-thiophenecarboxamide 499.5-chloro-N-[2-(exo- 6-(2-naphthyl)-3-azabicyclo[3.2.0]-heptan-3-yl)ethyl]-2-thiophenecarboxamide 500.N-[2-(exo-6-(1-naphthyl)-3-azabicyclo[3.2.0]heptan-3-yl)-ethyl]-4-fluorobenzamide 501.N-[2-(exo-6-(2-naphthyl)-3-azabicyclo[3.2.0]heptan-3-yl)-ethyl]-4-nitrobenzamide 0050/49558 ~ 02352526 2001-05-23 502.N-[2-(exo-6-(6-chloro-2-naphthyl)-3-azabicyclo[3.2.0]heptan-3-yl)ethyl]benzamide 503.N-[2-(exo-6-(1-naphthyl)-3-azabicyclo[3.2.0]heptan-3-yl)-ethyl]-4-methoxybenzamide 504.N-[2-(exo-6-(2-naphthyl)-3-azabicyclo[3.2.0]heptan-3-yl)-ethyl]-4-hydroxybenzamide 505.N-[2-(exo-6-(1-naphthyl)-3-azabicyclo[3.2.0]heptan-3-yl)-ethyl]-3,4-dichlorobenzamide 506.N-[2-(exo-6-(1-naphthyl)-3-azabicyclo[3.2.0]heptan-3-yl)-ethyl]naphthalene-1-carboxamide 507.N-[2-(exo-6-(2-naphthyl)-3-azabicyclo[3.2.0]heptan-3-yl)-ethyl]naphthalene-1-carboxamide 508.N-[2-(exo-6-(9-phenanthryl)-3-azabicyclo[3.2.0]heptan-3-yl)ethyl]benzamide 509.1-[2-(exo-6-(6-chloro-2-naphthyl)-3-azabicyclo[3.2.0]-heptan-3-yl)ethyl]-1H-benzo[cd]indol-2-one 510.1-[2-(exo-6-(9-phenanthryl)-3-azabicyclo[3.2.0]
heptan-3-yl)ethyl]-1H-benzo[cd]indol-2-one 511.N-[2-(exo-6-(1-naphthyl)-3-azabicyclo[3.2.0]heptan-3-yl)-ethyl]isoindolinone 512.N-[2-(exo-6-(2-naphthyl)-3-azabicyclo[3.2.0]heptan-3-yl)-ethyl]isoindolinone 513.(+)-(iS,5R,6S)exo-1-[2-[6-(4-chlorophenyl)-3-azabicyclo-[3.2.0]heptan-3-yl]ethyl]-3-methyl-2H-1,3-dihydro-benzimidazol-2-one 514.(+)-(1S,5R,6S)exo-1-[2-[6-(4-chlorophenyl)-3-azabicyclo-[3.2.0]heptan-3-yl]ethyl]-3-ethyl-2H-1,3-dihydro-benzimidazol-2-one 515.(+)-(iS,5R,6S)exo-1-[2-[6-(4-chlorophenyl)-3-azabicyclo-[3.2.0]heptan-3-yl]ethyl]-3-n-propyl-2H-1,3-dihydro-benzimidazol-2-one _ 0050/49558 ~ 02352526 2001-05-23 516.(+)-(1S,5R,6S)exo-2-[2-[6-(4-chlorophenyl)-3-azabicyclo-[3.2.0]heptan-3-yl]ethyl]-3,3-dimethyl-2,3-dihydro-1,2-benzisothiazole 1,1-dioxide 5 517.(+)-(1S,5R,6S)exo-2-[2-[6-(4-chlorophenyl)-3-azabicyclo-[3.2.0]heptan-3-yl]ethyl]-2,3-dihydro-1,2-benzisothiazole 1,1-dioxide 518.(+)-(1S,5R,6S)exo-2-[2-[6-(4-fluorophenyl)-3-azabicyclo-10 [3.2.0]heptan-3-yl]ethyl]-3,3-dimethyl-2,3-dihydro-1,2-benzisothiazole 1,1-dioxide 519.(+)-(1S,5R,6S)exo-2-[2-[6-(4-fluorophenyl)-3-azabicyclo-[3.2.0]heptan-3-yl]ethyl]-3,3-diethyl-2,3-dihydro-1,2-15 benzisothiazole 1,1-dioxide 520.(+)-(1S,5R,6S)exo-2-[2-[6-(4-fluorophenyl)-3-azabicyclo-[3.2.0]heptan-3-yl]ethyl]-2,3-dihydro-1,2-benzisothiazole 1,1-dioxide

Claims (4)

We claim:
1. The use of N-substituted 3-azabicycloalkane derivatives of the formula I

in which B is a 4-, 5- or 6-membered ring, which may contain a double bond, R1 is a phenyl, naphthyl, phenanthryl or thienyl group, in each case unsubstituted or mono- or disubstituted by halogen atoms, C1-4-alkyl, trifluoromethyl, hydroxyl, C1-4-alkoxy, amino, monomethylamino, dimethylamino, cyano or nitro groups, n is the number 0, 1, 2, 3 or 4 and R2 is a naphthyl group which is unsubstituted or substituted by one or two halogen atoms, or is one of the following radicals:

in which R3 is a hydrogen atom, a hydroxyl group or a phenyl radical which is unsubstituted or substituted by a fluorine, chlorine or bromine atom, R4 is a hydrogen atom or R3 and R4 together are an oxygen atom, R5 is a phenyl, naphthyl or thienyl group, each of which is unsubstituted or mono- or disubstituted by fluorine, chlorine or bromine atoms or by hydroxyl, nitro, amino, C1-4-alkanoylamino, C1-4-alkylamino, C1-4-alkyl or methoxy groups, R6 is a hydrogen atom or a methyl group, R7 is a phenyl, naphthyl, benzofuryl, benzothienyl, thienyl, indolyl, N-methylindolyl or indenyl group, in each case unsubstituted or mono- or disubstituted by fluorine, chlorine or bromine atoms or by C1-4-alkyl, hydroxyl, methoxy, nitro, cyano, trifluoromethyl, amino or di-C1-4-alkylamino groups, or is a C3-7-cycloalkyl group, R8 is a hydrogen atom or a fluorine or chlorine atom or a C1-4-alkyl, methoxy or amino group, R9 is a hydrogen atom or a methyl group and R10 is a hydrogen atom or a methyl group or R9 and R10 together with the ring carbon atom are a spirocyclopropane ring, R11 is a hydrogen atom, a hydroxyl, C1-C4-alkyl or C1-C4-alkoxy group, or together with the adjacent carbon atom is a C=O- or C=S group, X and Y are carbon atoms, CH, CH2, NH or C1-C4-alkyl-N
groups or nitrogen atoms, Z is a direct bond, a CO group, CS group or a CH or CH2 group in which a hydrogen atom may be replaced by a hydroxyl, amino or C1-C4-alkoxy group or by a halogen atom, and A is a hydrogen atom, a hydroxyl, amino, mercapto, C1-C4-alkylamino, di-C1-C4-alkylamino, C1-C4-alkylthio or C1-C4-alkoxy group or together with the adjacent carbon atom is a C=O group or A is a Y-bonded C3-C4-alkylene group which may contain one or two non-cumulated double bonds and in which one CH or CH2 group may be replaced by a nitrogen or sulfur atom or an NH or N-CH3 group and where the ring is either monosubstituted by a fluorine or chlorine atom or a methyl, methoxy, nitro or amino group or, in the case of a benzene ring, this may be mono-, di- or trisubstituted by fluorine or chlorine atoms or methyl, trifluoromethyl, vitro, hydroxyl, methoxy, amino, monomethyl or dimethylamino groups, and in which the X-, Y- and Z-containing ring at the nitrogen atom No. 1 may carry a C1-C4-alkyl, allyl or benzyl group and may contain 1 to 3 non-cumulated double bonds, and their salts with physiologically acceptable acids for preparing medicaments for treating disorders of the central nervous system.
2. The use as claimed in claim 1 for the production of drugs for treating addictive disorders.
3. The use as claimed in claim 1 or 2 for the production of drugs for treating cocaine addiction.
4. The use as claimed in claim 1 or 2 for the production of drugs for controlling addiction for amphetamines and amphetamine-like substances.
CA002352526A 1998-11-24 1999-11-12 Use of n-substituted azabicycloalkane derivatives for treating diseases of the central nervous system Abandoned CA2352526A1 (en)

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DE19854147A DE19854147A1 (en) 1998-11-24 1998-11-24 Control of cocaine addiction comprises administration of N-substituted azabicycloalkane derivative
DE19854147.3 1998-11-24
PCT/EP1999/008734 WO2000030639A1 (en) 1998-11-24 1999-11-12 Use of n-substituted azabicycloalkane derivatives for treating diseases of the central nervous system

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WO2014111837A1 (en) * 2013-01-15 2014-07-24 Novartis Ag Use of alpha 7 nicotinic acetylcholine receptor agonists

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US9096560B2 (en) 2008-07-03 2015-08-04 Syngenta Limited 5-heterocyclylalkyl-3-hydroxy-2-phenylcyclopent-2-enones as herbicides

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