AU1775300A - 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 PDFInfo
- Publication number
- AU1775300A AU1775300A AU17753/00A AU1775300A AU1775300A AU 1775300 A AU1775300 A AU 1775300A AU 17753/00 A AU17753/00 A AU 17753/00A AU 1775300 A AU1775300 A AU 1775300A AU 1775300 A AU1775300 A AU 1775300A
- Authority
- AU
- Australia
- Prior art keywords
- azabicyclo
- ethyl
- exo
- fluorophenyl
- heptan
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims description 9
- 210000003169 central nervous system Anatomy 0.000 title claims description 4
- 201000010099 disease Diseases 0.000 title 1
- -1 0Ci_ 4 -alkoxy Chemical group 0.000 claims description 31
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 229910052731 fluorine Inorganic materials 0.000 claims description 12
- 239000011737 fluorine Substances 0.000 claims description 12
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
- 125000001624 naphthyl group Chemical group 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000001544 thienyl group Chemical group 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 4
- 125000001246 bromo group Chemical group Br* 0.000 claims description 4
- 230000001955 cumulated effect Effects 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 206010012335 Dependence Diseases 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000001041 indolyl group Chemical group 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000005561 phenanthryl group Chemical group 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims 3
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 1
- 208000022497 Cocaine-Related disease Diseases 0.000 claims 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 1
- 201000006145 cocaine dependence Diseases 0.000 claims 1
- 206010013663 drug dependence Diseases 0.000 claims 1
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 158
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 60
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 50
- SDQJTWBNWQABLE-UHFFFAOYSA-N 1h-quinazoline-2,4-dione Chemical compound C1=CC=C2C(=O)NC(=O)NC2=C1 SDQJTWBNWQABLE-UHFFFAOYSA-N 0.000 description 32
- PCDHSSHKDZYLLI-UHFFFAOYSA-N butan-1-one Chemical compound CCC[C]=O PCDHSSHKDZYLLI-UHFFFAOYSA-N 0.000 description 27
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 26
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 19
- RMHJJUOPOWPRBP-UHFFFAOYSA-N naphthalene-1-carboxamide Chemical compound C1=CC=C2C(C(=O)N)=CC=CC2=C1 RMHJJUOPOWPRBP-UHFFFAOYSA-N 0.000 description 13
- YJJOJBNUDCBRTM-UHFFFAOYSA-N 5-ethyl-3,6-dimethyl-2-(methylamino)pyrimidin-4-one Chemical compound CCC1=C(C)N=C(NC)N(C)C1=O YJJOJBNUDCBRTM-UHFFFAOYSA-N 0.000 description 10
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 9
- JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical compound C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 6
- PXBFMLJZNCDSMP-UHFFFAOYSA-N 2-Aminobenzamide Chemical compound NC(=O)C1=CC=CC=C1N PXBFMLJZNCDSMP-UHFFFAOYSA-N 0.000 description 5
- LETMUHYAZQNEQL-UHFFFAOYSA-N 2-ethyl-7-methyl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound S1C(CC)=CN2C1=NC(C)=CC2=O LETMUHYAZQNEQL-UHFFFAOYSA-N 0.000 description 5
- BWNBLGQCCSCCHF-UHFFFAOYSA-N 2-ethyl-1h-indole Chemical compound C1=CC=C2NC(CC)=CC2=C1 BWNBLGQCCSCCHF-UHFFFAOYSA-N 0.000 description 4
- BDTRIDKONHOQQN-UHFFFAOYSA-N 4h-pyrimidin-5-one Chemical compound O=C1CN=CN=C1 BDTRIDKONHOQQN-UHFFFAOYSA-N 0.000 description 4
- GJDPKSPCTDQLKP-UHFFFAOYSA-N C(C)C1C=CN2C(S1)=NC(=CC2=O)C Chemical compound C(C)C1C=CN2C(S1)=NC(=CC2=O)C GJDPKSPCTDQLKP-UHFFFAOYSA-N 0.000 description 4
- 239000001273 butane Substances 0.000 description 4
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 description 3
- CVIBKISSHDMEKJ-UHFFFAOYSA-N 1-ethylquinazoline-2,4-dione Chemical compound C1=CC=C2C(=O)NC(=O)N(CC)C2=C1 CVIBKISSHDMEKJ-UHFFFAOYSA-N 0.000 description 3
- DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical compound O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 description 3
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 3
- PXZQEOJJUGGUIB-UHFFFAOYSA-N isoindolin-1-one Chemical compound C1=CC=C2C(=O)NCC2=C1 PXZQEOJJUGGUIB-UHFFFAOYSA-N 0.000 description 3
- DENPQNAWGQXKCU-UHFFFAOYSA-N thiophene-2-carboxamide Chemical compound NC(=O)C1=CC=CS1 DENPQNAWGQXKCU-UHFFFAOYSA-N 0.000 description 3
- CXUCKELNYMZTRT-UHFFFAOYSA-N 1-Ethyl-2-benzimidazolinone Chemical compound C1=CC=C2NC(=O)N(CC)C2=C1 CXUCKELNYMZTRT-UHFFFAOYSA-N 0.000 description 2
- CIGBERQUNYDMHH-UHFFFAOYSA-N 1H-indene-3-carboxamide Chemical compound C1=CC=C2C(C(=O)N)=CCC2=C1 CIGBERQUNYDMHH-UHFFFAOYSA-N 0.000 description 2
- QMNUDYFKZYBWQX-UHFFFAOYSA-N 1H-quinazolin-4-one Chemical compound C1=CC=C2C(=O)N=CNC2=C1 QMNUDYFKZYBWQX-UHFFFAOYSA-N 0.000 description 2
- LSGKMZLPZFPAIN-UHFFFAOYSA-N 1h-indole-3-carboxamide Chemical compound C1=CC=C2C(C(=O)N)=CNC2=C1 LSGKMZLPZFPAIN-UHFFFAOYSA-N 0.000 description 2
- BYXQNAWQFGHXDQ-UHFFFAOYSA-N 2-ethyl-7-methyl-2,3-dihydro-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound C(C)C1CN2C(=NC(=CC2=O)C)S1 BYXQNAWQFGHXDQ-UHFFFAOYSA-N 0.000 description 2
- LDZYRENCLPUXAX-UHFFFAOYSA-N 2-methyl-1h-benzimidazole Chemical compound C1=CC=C2NC(C)=NC2=C1 LDZYRENCLPUXAX-UHFFFAOYSA-N 0.000 description 2
- FIEYHAAMDAPVCH-UHFFFAOYSA-N 2-methyl-1h-quinazolin-4-one Chemical compound C1=CC=C2NC(C)=NC(=O)C2=C1 FIEYHAAMDAPVCH-UHFFFAOYSA-N 0.000 description 2
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 description 2
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 description 2
- RHJVIGLEIFVHIJ-UHFFFAOYSA-N cyclohexanecarboxamide Chemical compound NC(=O)C1[CH]CCCC1 RHJVIGLEIFVHIJ-UHFFFAOYSA-N 0.000 description 2
- OJEYDZBIAYMFFD-UHFFFAOYSA-N cyclopentanecarboxamide Chemical compound NC(=O)C1C[CH]CC1 OJEYDZBIAYMFFD-UHFFFAOYSA-N 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- QNLOWBMKUIXCOW-UHFFFAOYSA-N indol-2-one Chemical compound C1=CC=CC2=NC(=O)C=C21 QNLOWBMKUIXCOW-UHFFFAOYSA-N 0.000 description 2
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 2
- SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 1
- SEPPVOUBHWNCAW-FNORWQNLSA-N (E)-4-oxonon-2-enal Chemical compound CCCCCC(=O)\C=C\C=O SEPPVOUBHWNCAW-FNORWQNLSA-N 0.000 description 1
- KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 description 1
- BTNAZHHYONIOIV-UHFFFAOYSA-N 1,2-benzothiazole 1,1-dioxide Chemical compound C1=CC=C2S(=O)(=O)N=CC2=C1 BTNAZHHYONIOIV-UHFFFAOYSA-N 0.000 description 1
- JSDBKAHWADVXFU-UHFFFAOYSA-N 1,3-dimethyluracil Chemical compound CN1C=CC(=O)N(C)C1=O JSDBKAHWADVXFU-UHFFFAOYSA-N 0.000 description 1
- WJWHNTAKUNTHFX-UHFFFAOYSA-N 1-azabicyclo[3.2.0]heptane Chemical compound C1CCC2CCN21 WJWHNTAKUNTHFX-UHFFFAOYSA-N 0.000 description 1
- MWDPSEFHAGRCLG-UHFFFAOYSA-N 1-ethyl-7-methylimidazo[1,2-a]pyrimidin-5-one Chemical compound C(C)N1C=CN2C1=NC(=CC2=O)C MWDPSEFHAGRCLG-UHFFFAOYSA-N 0.000 description 1
- ASMIAPCOQULGEO-UHFFFAOYSA-N 1-ethylthieno[2,3-d]pyrimidine-2,4-dione Chemical compound O=C1NC(=O)N(CC)C2=C1C=CS2 ASMIAPCOQULGEO-UHFFFAOYSA-N 0.000 description 1
- PKVLOXUKWNLUNA-UHFFFAOYSA-N 1-ethylthieno[3,2-d]pyrimidine-2,4-dione Chemical compound C(C)N1C(NC(C2=C1C=CS2)=O)=O PKVLOXUKWNLUNA-UHFFFAOYSA-N 0.000 description 1
- AVSQGTAUBSVMBZ-UHFFFAOYSA-N 1-ethylthieno[3,4-d]pyrimidine-2,4-dione Chemical compound C(C)N1C(NC(C=2C1=CSC=2)=O)=O AVSQGTAUBSVMBZ-UHFFFAOYSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- 125000005978 1-naphthyloxy group Chemical group 0.000 description 1
- VFHUJFBEFDVZPJ-UHFFFAOYSA-N 1h-indole-2-carboxamide Chemical compound C1=CC=C2NC(C(=O)N)=CC2=C1 VFHUJFBEFDVZPJ-UHFFFAOYSA-N 0.000 description 1
- ROUMTDNDSNTIDN-UHFFFAOYSA-N 2,2-dimethylpentan-3-yloxybenzene Chemical compound CCC(C(C)(C)C)OC1=CC=CC=C1 ROUMTDNDSNTIDN-UHFFFAOYSA-N 0.000 description 1
- HMOMINHDSCYPKH-UHFFFAOYSA-N 2,5-dimethyl-1h-pyrimidin-6-one Chemical compound CC1=NC=C(C)C(=O)N1 HMOMINHDSCYPKH-UHFFFAOYSA-N 0.000 description 1
- UQFHLJKWYIJISA-UHFFFAOYSA-N 2,6-dimethyl-1h-pyrimidin-4-one Chemical compound CC1=CC(O)=NC(C)=N1 UQFHLJKWYIJISA-UHFFFAOYSA-N 0.000 description 1
- PGSBLIOCWDIEIB-UHFFFAOYSA-N 2,8-dimethylpyrido[1,2-a]pyrimidin-4-one Chemical compound C1=C(C)C=CN2C1=NC(C)=CC2=O PGSBLIOCWDIEIB-UHFFFAOYSA-N 0.000 description 1
- 125000003163 2-(2-naphthyl)ethyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(C([H])=C([H])C2=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- BKIGMBKKKHQCGW-UHFFFAOYSA-N 2-amino-3,5-diethyl-6-methylpyrimidin-4-one Chemical compound CCC1=C(C)N=C(N)N(CC)C1=O BKIGMBKKKHQCGW-UHFFFAOYSA-N 0.000 description 1
- ZBZFHKRVXVKBOU-UHFFFAOYSA-N 2-amino-3-ethyl-6-methylpyrimidin-4-one Chemical compound CCN1C(N)=NC(C)=CC1=O ZBZFHKRVXVKBOU-UHFFFAOYSA-N 0.000 description 1
- ASSKVPFEZFQQNQ-UHFFFAOYSA-N 2-benzoxazolinone Chemical compound C1=CC=C2OC(O)=NC2=C1 ASSKVPFEZFQQNQ-UHFFFAOYSA-N 0.000 description 1
- QHCCOYAKYCWDOJ-UHFFFAOYSA-N 2-ethyl-1h-benzimidazole Chemical compound C1=CC=C2NC(CC)=NC2=C1 QHCCOYAKYCWDOJ-UHFFFAOYSA-N 0.000 description 1
- DFJIYTCXFYGSLR-UHFFFAOYSA-N 2-ethyl-3-heptan-3-yl-7-methyl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound CCC(CCCC)C1=C(SC=2N1C(C=C(N=2)C)=O)CC DFJIYTCXFYGSLR-UHFFFAOYSA-N 0.000 description 1
- CJCVPBLPKUXYKO-UHFFFAOYSA-N 2-ethyl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound S1C(CC)=CN2C1=NC=CC2=O CJCVPBLPKUXYKO-UHFFFAOYSA-N 0.000 description 1
- MPFMDBDLIURSOD-UHFFFAOYSA-N 2-methyl-1h-quinazoline-4-thione Chemical compound C1=CC=C2NC(C)=NC(=S)C2=C1 MPFMDBDLIURSOD-UHFFFAOYSA-N 0.000 description 1
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- IZTRYCWBEAGXLS-UHFFFAOYSA-N 3,5-diethyl-6-methyl-2-(methylamino)pyrimidin-4-one Chemical compound C(C)C=1C(N(C(=NC=1C)NC)CC)=O IZTRYCWBEAGXLS-UHFFFAOYSA-N 0.000 description 1
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- QFAZKRBHISMWEG-UHFFFAOYSA-N 3-ethyl-1-methylpyrido[2,3-d]pyrimidine-2,4-dione Chemical compound C(C)N1C(N(C2=C(C1=O)C=CC=N2)C)=O QFAZKRBHISMWEG-UHFFFAOYSA-N 0.000 description 1
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- OMOBWMBJNNCUFO-UHFFFAOYSA-N 5-chlorothiophene-2-carboxamide Chemical compound NC(=O)C1=CC=C(Cl)S1 OMOBWMBJNNCUFO-UHFFFAOYSA-N 0.000 description 1
- PXDDCBOOHGDLBL-UHFFFAOYSA-N 5-methyl-1h-quinazolin-4-one Chemical compound N1C=NC(=O)C2=C1C=CC=C2C PXDDCBOOHGDLBL-UHFFFAOYSA-N 0.000 description 1
- SDIRSOYPVNRKED-UHFFFAOYSA-N 6-ethyl-2,3,7-trimethyl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound C(C)C1=C(N=C2N(C1=O)C(=C(S2)C)C)C SDIRSOYPVNRKED-UHFFFAOYSA-N 0.000 description 1
- NYBDRQJPWDONJD-UHFFFAOYSA-N 7-chloro-3-ethyl-2-methylpyrimido[1,2-a]pyrimidin-4-one Chemical compound C(C)C1=C(N=C2N(C1=O)C=C(C=N2)Cl)C NYBDRQJPWDONJD-UHFFFAOYSA-N 0.000 description 1
- KDLTYKUHEDMZDJ-UHFFFAOYSA-N 8-methyl-2h-pyrimido[2,1-b][1,3]thiazin-6-one Chemical compound C1=CCSC2=NC(C)=CC(=O)N21 KDLTYKUHEDMZDJ-UHFFFAOYSA-N 0.000 description 1
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 1
- YCIPQJTZJGUXND-UHFFFAOYSA-N Aglaia odorata Alkaloid Natural products C1=CC(OC)=CC=C1C1(C(C=2C(=O)N3CCCC3=NC=22)C=3C=CC=CC=3)C2(O)C2=C(OC)C=C(OC)C=C2O1 YCIPQJTZJGUXND-UHFFFAOYSA-N 0.000 description 1
- GOEQLTJCLUKOFD-UHFFFAOYSA-N CCC1=C(C)N=C(N)N(C)C1=O Chemical compound CCC1=C(C)N=C(N)N(C)C1=O GOEQLTJCLUKOFD-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 102000004300 GABA-A Receptors Human genes 0.000 description 1
- 108090000839 GABA-A Receptors Proteins 0.000 description 1
- 208000001613 Gambling Diseases 0.000 description 1
- GVGLGOZIDCSQPN-PVHGPHFFSA-N Heroin Chemical compound O([C@H]1[C@H](C=C[C@H]23)OC(C)=O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4OC(C)=O GVGLGOZIDCSQPN-PVHGPHFFSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- 229940025084 amphetamine Drugs 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- MYONAGGJKCJOBT-UHFFFAOYSA-N benzimidazol-2-one Chemical compound C1=CC=CC2=NC(=O)N=C21 MYONAGGJKCJOBT-UHFFFAOYSA-N 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 229940049706 benzodiazepine Drugs 0.000 description 1
- 125000003310 benzodiazepinyl group Chemical class N1N=C(C=CC2=C1C=CC=C2)* 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229960003920 cocaine Drugs 0.000 description 1
- 230000003920 cognitive function Effects 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- AIMMVWOEOZMVMS-UHFFFAOYSA-N cyclopropanecarboxamide Chemical compound NC(=O)C1CC1 AIMMVWOEOZMVMS-UHFFFAOYSA-N 0.000 description 1
- 229960002069 diamorphine Drugs 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- PUSKHXMZPOMNTQ-UHFFFAOYSA-N ethyl 2,1,3-benzoselenadiazole-5-carboxylate Chemical compound CCOC(=O)C1=CC=C2N=[Se]=NC2=C1 PUSKHXMZPOMNTQ-UHFFFAOYSA-N 0.000 description 1
- UMPRJGKLMUDRHL-UHFFFAOYSA-N ethyl 4-fluorobenzoate Chemical compound CCOC(=O)C1=CC=C(F)C=C1 UMPRJGKLMUDRHL-UHFFFAOYSA-N 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000007941 film coated tablet Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 208000013403 hyperactivity Diseases 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- WRSXUNSJGJUKHE-UHFFFAOYSA-N indazole Chemical compound C1=CC=C[C]2C=NN=C21 WRSXUNSJGJUKHE-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- XBCXJKGHPABGSD-UHFFFAOYSA-N methyluracil Natural products CN1C=CC(=O)NC1=O XBCXJKGHPABGSD-UHFFFAOYSA-N 0.000 description 1
- 229960005181 morphine Drugs 0.000 description 1
- 229960002715 nicotine Drugs 0.000 description 1
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 229940005483 opioid analgesics Drugs 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- UFUASNAHBMBJIX-UHFFFAOYSA-N propan-1-one Chemical compound CC[C]=O UFUASNAHBMBJIX-UHFFFAOYSA-N 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- DSNYFFJTZPIKFZ-UHFFFAOYSA-N propoxybenzene Chemical compound CCCOC1=CC=CC=C1 DSNYFFJTZPIKFZ-UHFFFAOYSA-N 0.000 description 1
- VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical compound OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 description 1
- FFRYUAVNPBUEIC-UHFFFAOYSA-N quinoxalin-2-ol Chemical compound C1=CC=CC2=NC(O)=CN=C21 FFRYUAVNPBUEIC-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 229960000581 salicylamide Drugs 0.000 description 1
- 229940125723 sedative agent Drugs 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000007940 sugar coated tablet Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000007885 tablet disintegrant Substances 0.000 description 1
- IOHCGRJBQIIEOU-UHFFFAOYSA-N thiazin-6-one Chemical compound O=C1C=CC=NS1 IOHCGRJBQIIEOU-UHFFFAOYSA-N 0.000 description 1
- RWQNBRDOKXIBIV-UHFFFAOYSA-N thymine Chemical compound CC1=CNC(=O)NC1=O RWQNBRDOKXIBIV-UHFFFAOYSA-N 0.000 description 1
- 239000003204 tranquilizing agent Substances 0.000 description 1
- 230000002936 tranquilizing effect Effects 0.000 description 1
- 229940035893 uracil Drugs 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical & Material Sciences (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Psychiatry (AREA)
- Addiction (AREA)
- Epidemiology (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Indole Compounds (AREA)
Description
Use of N-substituted azabicycloalkane derivatives for treating disorders of the central nervous system 5 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 10 central nervous system. The present invention provides the use of N-substituted 3-azabicycloalkane derivatives of the formula I 15 RI 1 N-(CH2)n-R2 in which 20 B is a 4-, 5- or 6-membered ring, which may contain a double bond,
R
1 is a phenyl, naphthyl, phenanthryl or thienyl group, in. each 25 case unsubstituted or mono- or disubstituted by halogen atoms, CI.
4 -alkyl, trifluoromethyl, hydroxyl, C 1 -4-alkoxy, amino, monomethylamino, dimethylamino, cyano or nitro groups, n is the number 0, 1, 2, 3 or 4 and 30
R
2 is a naphthyl group which is unsubstituted or substituted by one or two halogen atoms, or is one of the following radicals: 35 40 45 2
R
3 - R 5 - NR 6 -C - R 7 ' -NR 6
-SO
2 Q 5 R
-NR
6 R -O -- R 10 R8 -N / R 8 0 15 0
R
8 N R9 200 20 -NR0-N 0 RIO ,N -NR0R 25 O CH3 R -- N \N '-- R N A N R9
H
3 C N N z 30 R8 O R8 0 2 S 0 35 or in which 40 R 3 is a hydrogen atom, a hydroxyl group or a phenyl radical which is unsubstituted or substituted by a fluorine, chlorine or bromine atom,
R
4 is a hydrogen atom or 45
R
3 and R 4 together are an oxygen atom, 3
R
5 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,
C
1
.
4 -alkanoylamino, C 1
-.
4 -alkylamino, C 1
-
4 -alkyl or methoxy 5 groups,
R
6 is a hydrogen atom or a methyl group,
R
7 is a phenyl, naphthyl, benzofuryl, benzothienyl, thienyl, 10 indolyl, N-methylindolyl or indenyl group, in each case unsubstituted or mono- or disubstituted by fluorine, chlorine or bromine atoms or by Ci- 4 -alkyl, hydroxyl, methoxy, nitro, cyano, trifluoromethyl, amino or di-C 1
.
4 -alkylamino groups, or is a C 3
-
7 -cycloalkyl group, 15
R
8 is a hydrogen atom or a fluorine or chlorine atom or a
C
1
-
4 -alkyl, methoxy or amino group,
R
9 is a hydrogen atom or a methyl group and 20
R
10 is a hydrogen atom or a methyl group or
R
9 and R 10 together with the ring carbon atom are a spirocyclopropane ring, 25
R
11 is a hydrogen atom, a hydroxyl, Ci-C 4 -alkyl or Ci-C 4 -alkoxy group, or together with the adjacent carbon atom is a C=0- or C=S group, 30 X and Y are carbon atoms, CH, CH 2 , NH or Ci-C 4 -alkyl-N groups or nitrogen atoms, Z is a direct bond, a CO group, CS group or a CH or CH 2 group in which a hydrogen atom may be replaced by a hydroxyl, amino or 35 Ci-C 4 -alkoxy group or by a halogen atom, and A is a hydrogen atom, a hydroxyl, amino, mercapto, Ci-C 4 -alkylamino, di-Ci-C 4 -alkylamino, Ci-C 4 -alkylthio or Ci-C 4 -alkoxy group or together with the adjacent carbon atom 40 is a C=O group or A is a Y-bonded C 3
-C
4 -alkylene group which may contain one or two non-cumulated double bonds and in which one CH or CH 2 group may be replaced by a nitrogen or sulfur atom or an NH 45 or N-CH 3 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 4 mono-, di- or trisubstituted by fluorine or chlorine atoms or methyl, trifluoromethyl, nitro, hydroxyl, methoxy, amino, monomethyl or dimethylamino groups, 5 and in which the X-, Y- and S-containing ring at the nitrogen atom No. 1 may carry a Ci-C 4 -alkyl, allyl or benzyl group and may contain 1 to 3 non-cumulated double bonds, and their salts with physiologically acceptable acids for 10 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). 15 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: 20 opioids such as, for example, morphine or heroin, nicotine, alcohol, substances which interact with the benzodiazepine receptor 25 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 30 substances. The compounds of the formula I can be employed both in the form of their racemates and their optical isomers. 35 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 40 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. 45 The compounds can be employed in customary galenic administration forms, in solid or liquid form, for example as tablets, film-coated tablets, capsules, powders, granules, 5 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 galenic 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 10 administration forms usually comprise the active compound in an amount of 1 to 99% by weight. The following substances may be mentioned as examples of compounds of the formula I: 15 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[3.2.0]heptan-3-yl 20 butan-1-one 3. 1-(4-fluorophenyl)-4-[exo-6,7-diphenyl-3-azabicyclo [3.2.0]heptan-3-yl]butan-1-one 25 4. 1-(4-fluorophenyl)-4-[exo-6-phenyl-3-azabicyclo[3.2.0] heptan-3-yl]butane 5. 1-phenyl-2-[exo-6-phenyl-3-azabicyclo[3.2.0]heptan-3-yl] ethan-1-one 30 6. 1-(4-fluorophenyl)-4-[exo-6-p-fluorophenyl-3-azabicyclo [3.2.0]heptan-3-ylJbutane 7. 1-(4-fluorophenyl)-4-[exo-6-m-fluorophenyl-3-azabicyclo 35 [ 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-ylJbutan-1-one 40 9. 1-(4-fluorophenyl)-4-[exo-6-p-chlorophenyl-3-azabicyclo [3.2.0]heptan-3-ylJbutan-l-one 10. 1-(4-fluorophenyl)-4-[exo-6-m-chlorophenyl-3-azabicyclo [3.2.0]heptan-3-yl]butan-1-one 45 6 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 5 [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 10 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 15 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 20 [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 25 19. 1-( 4 -fluorophenyl)-4-[exo-6-p-trifluoromethylphenyl-3 azabicyclo[3.2.0]heptan-3-yl]butan-1-one 20. 1-( 4 -fluorophenyl)-4-[exo-6-p-cyanophenyl-3-azabicyclo [3.2.0]heptan-3-yl]butan-1-one 30 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 35 [ 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 40 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 45 7 26. 1-(4-fluorophenyl)-4-[exo-6-phenyl-3-azabicyclo[3.2.O] heptan-3-yl ]butan-1-ol 27. 1- (4-f luorophenyl )-4- [exo-6-p-fluorophenyl-3-azabicyclo * 5 (3.2.Ojheptan-3-yl]butan-l-ol 28. .1-(4-fluorophenyl)-4-[exo-6,7-diphenyl-3-azabicyclo[3.2.O] heptan-3-yl ]butan-1-ol 10 29. 1-phenyl-4-[exo-6-phenyl-3-azabicyclo[3.2.0]heptan-3-yl] butan-l-ol 30. 1-phenyl-4-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.o] heptan-3-yl ]butan-1-ol 15 31. 1-(4-fluorophenyl)-4-[exo-6-o-fluorophenyl-3-azabicyclo [3.2 .0]heptan-3-yl]butan-l-ol 32. 1-( 4-fluorophenyl)-4-[exo-6-m-chlorophenyl-3-azabicyclo 20 [3.2.O]heptan-3-yl]butan-l-ol 33. 1- (4-f luorophenyl) -4- [exo-6-p-trifluoromethylphenyl-3 azabicyclo[ 3.2.0] heptan-3-yl ]butan-1-ol 25 34. 1-( 4-f luorophenyl)-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 30 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] 35 ethyl )-4-f luorobenzamide 38. N-(2-[exo-6-phenyl-3-azabicyclo[3.2.0]heptan-3-yl] ethyl )benzamide 40 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-methylbenzanide 45 8 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] 5 propyl) -4-chlorobenzamide 43. N-( 2 -[exo-6-p-trifluoromethylphenyl-3-azabicyclo[3.2.0] heptan-3-yl]ethyl)-4-chlorobenzamide 10 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 15 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 20 3-yl]propyl)benzamide 48. N-( 2 -[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan 3-yl]ethyl)-4-fluorobenzamide 25 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 30 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 35 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 40 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 45 9 56. N-(2-[exo-6-m-chlorophenyl-3-azabicyclo( 3.2 .0]heptan 3 -ylJ ethyl )-4-chlorobenzamide 57. N-(2-[exo-6-o-fluorophenyl-3-azabicyclo[3.2.0]heptan 5 3-yl methyl )-4-chlorobenzamide 58. N-(2-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan 3-yl ]ethyl) -2-hydroxybenzamide 10 59. N-(2-[exo-6-m-hydroxyphenyl-3-azabicyclo[3.2.O]heptan-3-ylJ ethyl) -4-chlorobenzamide 60. exo-3-n-butyl-6-phenyl-3-azabicyclo[3 .2 .0]heptane 15 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-filuorophenyl-3-azabicyclof 3.2.0] 20 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] 25 heptane 66. exo-3-allyl-6-m-methoxyphenyl-3-azabicyclo[3.2.0] heptane 30 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 35 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] 40 heptane 71. 6-1-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl] ethyl-7-methyl-5H-thiazolo( 3, 2-a]pyrimidin-5-one 45 72. (+)-6-1-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan 3-yllethyl-7-methyl-5H-thiazolo[ 3, 2-a]pyrimidin-5-one 10 73. (-)-6-B-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan 3-yl]ethyl-7-methyl-5H-thiazolo[3,2-a]pyrimidin-5-one 74. 6-B-[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-B-[exo-6,7-diphenyl-3-azabicyclo[3.2.0]heptan-3-yl]ethyl 7-methyl-5H-thiazolo[3,2-a]pyrimidin-5-one 10 76. 6-B-[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-B-[exo-6-m-chlorophenyl-3-azabicyclo[3.2.0]heptan-3-yl] ethyl-7-methyl-5H-thiazolo[3,2-a]pyrimidin-5-one 15 78. 6-B-[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-B-[exo-6-m-hydroxyphenyl-3-azabicyclo[3.2.0]heptan 20 3-yl]ethyl-7-methyl-5H-thiazolo[3,2-a]pyrimidin-5-one 80. 6-B-(2-[exo-6-p-aminophenyl-3-azabicyclo[3.2.0]heptan 3-yl]ethyl-7-methyl-5H-thiazolo[3,2-a]pyrimidin-5-one 25 81. 6-B-[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-B-[exo-6-p-methoxyphenyl-3-azabicyclo[3.2.0]heptan 3-yl]ethyl-7-methyl-5H-thiazolo[3,2-a]pyrimidin-5-one 30 83. 6-B-[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[3.2.0]heptan 35 3-yl]ethyl-7-methyl-5H-thiazolo[3,2-a]pyrimidin-5-one 85. 6-B-[exo-6-p-hydroxyphenyl-3-azabicyclo[3.2.0]heptan 3-yl]ethyl-7-methyl-5H-thiazolo[3,2-a]pyrimidin-5-one 40 86. 6-B-[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-B-[exo-6-(p-t-butylphenyl)-3-azabicyclo[3.2.0]heptan 45 3-yl]ethyl-7-methyl-5H-thiazolo[3,2-a]pyrimidin-5-one 11 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-B-[exo-6-(3,4-dichlorophenyl)-3-azabicyclo[3.2.0]heptan 5 3-yl]ethyl-7-methyl-5H-thiazolo[3,2-a]pyrimidin-5-one 90. 6-B-[exo-6-(3,4-dimethoxyphenyl)-3-azabicyclo[3.2.0] heptan-3-yl]ethyl-7-methyl-5H-thiazolo[3,2-a]pyrimidin 5-one 10 91. 6-B-[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-B-[exo-6-(3,4-dihydroxyphenyl)-3-azabicyclo[3.2.O] 15 heptan-3-ylethyl-7-methyl-5H-thiazolo[3,2-a]pyrimidin 5-one 93. 6-B-[exo-6-(o-fluorophenyl)-3-azabicyclo[3.2.0]heptan 3-yl]ethyl-7-methyl-5H-thiazolo[3,2-a]pyrimidin-5-one 20 94. 6-B-[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- 25 3-yl]ethyl-7-methyl-5H-thiazolo[ 3,2-a]pyrimidin-5-one 96. 6-B-[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 30 97. 6-B-[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 35 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 40 100. 6-B-[exo-6-phenyl-3-azabicyclo[3.2.Oheptan-3-yl]ethyl-5H thiazolo[3,2-a]pyrimidin-5-one 101. 7-B-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.]heptan-3-yl] 45 ethyl-8-methyl-2H,6H-pyrimido[ 2 ,1-b][1,3]thiazin-6-one 12 102. 7-1-[exo-6-phenyl-3-azabicyclo[3 .2 .0]heptan-3-yllethyl 8-methyl-2H,6H-pyrimido[2,1-b] [1,3]thiazin-6-one 103. 7-B-[exo-6-ni-chlorophenyl-3-azabicyclo[3 .2 .0]heptan-3-yl] 5 ethyl-8-methyl-2H,6H-pyrimido[2,1-b] [1,3]thiazin-6-one 104. 7-B-[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 10 105. 7-1-[exo-6-p-methoxyphenyl-3-azabicyclo[3 .2 .0]heptan-3-yl] ethyl-8-methyl-2H,6H-pyrimidot 2,1-b] [1.3]thiazin-6-one 106. 7-1-[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 15 107. 3-1-[exo-6-p-fluoropheflyl-3-azabicyclo[3 .2 .0]heptan-3-yl] ethyl-2,4-( 1H,3H)quinazolinedione 108. (+)-3-I3-[exo-6-p-fluorophefl-3-azabicyclo[3.2.0]heptal 20 3-yl]ethyl-2,4-(H,3H)quiazoiediofle 109. (-)-3-I3[exo-6-p-fluorophefl1-3-azabicyc1o[3.2.0]heptan 3-yl ]ethyl-2, 4- ( H,3H )quinazolinedione 25 110.3--eo6pey -aaiyl[..]epa--lehl24 (1H, 3H)quinazolinedione 111. 3-1-[exo-6-m-fluorophenyl-3-azabicyclo[3 .2 .0]heptan-3-yl] ethyl-2 ,4- ( H, 3H )quinazolinedione 30 112. 3-J3[exo6-p-cyanopheny-3-azabicyclo[3.2.0]heptaf 3 yl] ethyl-2, 4- ( H, 3H)quinazolinediole 113. 3-13-[exo-6-m-chlorophenyl-3-azabicyclo[3 .2 .0]heptan-3-yl] 35 ethyl-2,4-( 1H,3H)quinazolinedione 114. 3-13-[exo-6-p-hydroxyphenyl-3-azabicyclo[3 .2 .0]heptan-3-yl] ethyl-2, 4-( H, 3H )quinazolinedione 40 115. 3-B-[exo-6-p-chlorophenyl-3-azabicyclo[3.2.0]heptaf 3 -yl] ethyl-2,4-( 1H,3H)quinazolinedione 116. 3-1-[exo-6-m-methoxyphenyl-3-azabicyclo[3 .2 .0]heptan-3-yl] ethyl-2 ,4- ( H, 3H ) uinazolinedione 45 13 117. 3-1-[exo-6-p-nitrophenyl-3-azabicyclo[3.2 .O]heptan-3-yl] ethyl-2, 4- ( H, 3H )quinazolinedione 118. 3-1-[endo-6-p-nitrophenyl-3-azabicyclo[3 .2 .0]heptan-3-ylJ 5 ethyl-2 ,4-( 1H, 3H)quinazolinedione 119. 3-1-[exo-6-m-hydroxyphenyl-3-azabicyclo[3 .2 .O]heptan-3-yl] ethyl-2, 4-( 1H, 3H)quinazolinedione 10 120. 3-1-[exo-6-p-aiinophenyl-3-azabicyclo[3.2.0]heptafl-3-y1) ethyl-2 ,4-( 1H, 3H)quinazolinedione 121. 3-3-[exo-6-p-iodophenyl-3-azabicycloE 3.2 .0]heptan-3-yl) ethyl-2 ,4-( 1H, 3H)quinazolinedione 15 122. 3-B-[exo-6-p-trifluoromethylpheflyl-3-azabicyclo[3.2 .0] heptan-3-yl]ethyl-2,4-( 1H,3H)quinazolinedione 123. 3-J3-exo-6-(3,4-dichlorophenyl)-3-azabicyclo[3.2.0] 20 heptan-3-yl]ethyl-2,4-( 1H,3H)quinazolinedione 124. 3-i-[exo-6-(3,4-dihydroxyphenyl)-3-azabicyclo[3.2.0] heptan-3-yl ]ethyl-2, 4- ( H, 3H )quinazolinedione 25 125. 3-i3[exo-6-(3,5-dichlorophenyl)-3-azabicyc1o[3.2.0]heptal 3-yl]ethyl-2,4-(lH,3H)quinazolinediofle 126. 3-1-[exo-6-o-fluorophenyl-3-azabicyclo[3.2.0]heptal-3-y1] ethyl-2, 4- ( H, 3H )quinazolinedione 30 127. 3-1-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptal-3-y1J ethyl-8 -methyl-2, 4- ( H, 3H )quinazolinedione 128. 3--[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptal-3-y1] 35 ethyl-7-chloro-2, 4- ( H, 3H )quinazolinedione 129. 3-13-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptal-3-y1] ethyl-7-fluoro-2,4-( 1H,3H)quinazolinedione 40 130. 3-13-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptal-3-y1J ethyl-5-chloro-2, 4-( 1H, 3H)quinazolinedione 131. 3-B-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptal-3-y1] ethyl-6-fluoro-2, 4- ( H, 3H )quinazolinedione 45 14 132. 3--eo6pfurpey--zaiyl[..]etn3y] ethyl-6-methyl-2, 4- ( H,3H )quinazolinedione 133. 3-J3-exo-6-p-fluoropheflyl-3-azabicyc1Q( 3 .2 .0]heptan-3-yl] 5 ethyl-8-methoxy-2,4-( 1H,3H)quinazolinediofle 134.3--eo6pfurpey -zaiyl[..]etn3y] ethyl-6 -trif luoromethyl-2, 4- ( H, 3H )quinazolinedione 10 135. 3--eo6pfurpey--zaiyl[..]etn3y] ethyl-7-nitro-2,4-( 1H, 3H)quinazolinediofle 136.3--eo6pfurpey -zaiyl[..]etn3y] ethyl-6-nitro-2 ,4-( 1H, 3H)quinazolinedione 15 137.3--eo6pfurpey -zaiyl[..]etn3y] ethyl-7-amino-2,4-( 1H,3H)quinazolinedione 138.3--eo6pfurpey -zaiyl[..]etn3yl 20 ethyl-6-amino-2,4-( 1H,3H)quinazolinediofle 139.3--eo6pfloohnl3-zbcco3.2 .0]heptan-3-yl] ethyl-6-hydroxy-2 ,4-( 1H, 3H)quinazolinediofle 25 140.3--eo6pfurpey -zaiyl[..]etn3y] ethyl-5-chloro-2, 4- ( H,3H )quinazolinedione 141.3--eo6pfurpey -zaiyl[..]etn3y] ethyl-6, 7-dimethoxy-2, 4- ( H,3H )quinazolinedione 30 142.3--eo6pfurpey -zaiyl[..]etn3y] ethyl-6, 8-dichloro-2 ,4- ( H, 3H )quinazolinedione 143.3--eo6pfurpey -zaiyl[..letn3y] 35 ethyl-6, 7, 8-trimethoxy-2,4-( 1H, 3H)quinazolinediofle 144.3--eo6pfurpey -zaiyl[..]etn3y] ethyl-i -methyl-2, 4- ( H, 3H )quinazolinedione 40 145.3--eo6pfurpey -zaiyl[..]etn3y] ethyl-1-ethyl-2, 4-( 1H, 3H)quinazolinediofle 146. 3-B-[exo-6-p-fluoropheflyl-3-azabicyclo[ 3 .2 .O]heptan-3-yl] ethyl-1-allyl-2, 4- ( H, 3H )quin-azolinedione 45 15 147. 3-B-[exo-6-p-fluorophenyl-3-azabicyclo[3 .2 .O]heptan-3-yl] ethyl-l-benzyl-2 ,4-( e, 3H)quinazolinedione 148. 3-y-[exo-6-p-fluorophenyl-3-azabicyclo[3 .2 .O]heptan-3-yl] 5 propyl-2,4-( 1H,3H)quinazolinedione 149. 3-6-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.O]heptan-3-yl] butyl-2, 4- ( H, 3H )quinazolinedione 10 150. 3-1-[exo-6-(2-thienyl)-3-azabicyclo[3.2.O]heptan-3-yl] ethyl-2,4-( 1H, 3H)quinazolinedione 151. 3-1-[exo-6-(5-chloro-2-thienyl)-3-azabicyclo[3.2.O]heptan 3-yl]ethyl-2,4-(1H,3H)quinazolinedione 15 152. 3-1-[exo-6-(3-thienyl)-3-azabicyclo[3.2.O]heptan-3-yl] ethyl-2, 4- ( H, 3H )quinazolinedione 153. 3-1-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl] 20 ethyl-1H-thieno[3,2-d]pyrimidine-2,4-dione 154. 3-i-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl] ethyl-1H-thieno[ 2, 3-d]pyrimidine-2, 4-dione 25 155. 3-1-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl] ethyl-1H-thieno[ 3, 4-d]pyrimidine-2, 4-dione 156. 3-B-[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 30 157. 3-1-exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl] ethyl-2 -methyl-3H-quinazolin-4 -one 158. 3-i-[exo-6-p-fluorophenyl-3-azabicyclo[ 3.2 .0]heptan-3-yl] 35 ethyl-2-methoxy-3H-quinazolin-4-one 159. 3-B-[exo-6-p-fluorophenyl-3-azabicyclo[3 .2. Ojheptan-3-yl] ethyl-2-methyl-4H-pyrido( 1, 2-a]pyrimidin-4-one dihydrochioride 40 160. 3-1-[exo-6-phenyl-3-azabicyclo[3 .2 .0]heptan-3-yl]ethyl 2-methyl-4H-pyrido[ 1,2-a ]pyrimidin-4-one 161. 3-B-[exo-6-m-chlorophenyl-3-azabicyclo[3 .2. 0]heptan-3-yl] 45 ethyl-2-methyl-4H-pyrido[ 1,2-a]pyrimidin-4-one 16 162. 3-B-[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-J-[exo-6-p-fluoropheny1-3-azabicyc1o[3.2.O]heptal 5 3-yl]ethyl-2 ,6-dimethyl-4H-pyrido[ 1,2-a]pyrimidin-4-ofle 164. 3-I3-[exo-6-p-fluoropheny1-3-azabicyclo[3.2.O]heptal 3-yl ]ethyl-2, 7-dimethyl-4H-pyrido[ 1, 2-a]pyrimidin-4-one 10 165. 3-J3-fexo-6-p-fluorophenyl-3-azabicyc1o[3.2.O]heptal 3-yl ]ethyl-2, 8-dimethyl-4H-pyrido[ 1,2-a ]pyrimidin-4-one 166. 3-1-[exo-6-p-fluorophenyl-3-azabicycloI 3.2 .0]heptan 3-yl ]ethyl-2, 9-dimethyl-4H-pyrido[ 1, 2-a]pyrimidin-4-one 15 167. 3-1-[exo-6-p-fluorophenyl-3-azabicyclo[ 3.2 .O]heptan 3-yl ]ethyl-2, 6, 8-trimethyl-4H-pyrido[ 1, 2-a]pyrimidin-4-one 168. 3-1-[exo-6-m-chlorophenyl-3-azabicyclo[3 .2 .O]heptan 20 3-yljethyl-2, 7-dimethyl-4H-pyrido( 1,2-a]pyrimidin-4-one 169. 3-i3[exo-6-o-fluorophenyl-3-azabicyclo[3.2.O]heptal 3-yl]ethyl-2,7-dimethyl-4H-pyrido( 1,2-a]pyrimidin-4-one 25 170. 3-I3[exo-6-pheny1-3-azabicyclo[3.2.O]heptafl-3-yl]ethylN 2, 8-dimethyl-4H-pyrido[ 1, 2-a]pyrimidin-4-one 171. 3-i-[exo-6-m-chlorophenyl-3-azabicyclo( 3.2 .0]heptan 3-yl]ethyl-2, 9-dimethyl-4H-pyrido[ 1,2-alpyrimidin-4-one 30 172.3 3-J3[exo-6-(5-chlorothien-2-y1)-3-azabicyc1o[3.2.0]heptal" 3-yl]ethyl-2-methyl-4H-pyrido[ 1,2-a]pyrimidin-4-one 173. 3-B-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptaf3-yl] 35 ethyl-6, 7,8, 9-tetrahydro-2-methyl-4H-pyrido( 1,2-a]pyrimidin 4-one 174. 3-J3[exo6-p-choropheny-3-azabicyclo[3.2.0]heptaf 3 -ylV ethyl-6 ,7,8, 9-tetrahydro-2-methyl-4H-pyrido[ 1,2-a]pyrimidin 40 4-one 175. 3-J-[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 45 17 176. 3-B-[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-B-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl] 5 ethyl-2-methyl-7-chloro-4H-pyrimido[1,2-a]pyrimidin-4-one 178. 6-B-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl] ethyl-7-methyl-1H,5H-imidazo[1,2-a]pyrimidin-5-one 10 179. 3-B-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-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] 15 methylbenzimidazole 181. -B-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl] ethylbenzimidazole 20 182. 1-B-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0heptan-3-yl] ethyl-2,3-dihydrobenzimidazol-2-one 183.2-[exo-6-m-methoxyphenyl-3-azabicyclo[3.2.0]heptan-3-yl) methylbenzimidazole 25 184.3-B-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl] ethylindole, m.p. 193-195 0 C (hydrochloride) 185. 3--(2-[exo-6-m-chlorophenyl-3-azabicyclo[3.2.0]heptan-3 30 yl]ethylindole 186. 3--[exo-6-phenyl-3-azabicyclo[3.2.0]heptan-3-yl]ethyl indole, m.p. 104-1050C (hydrochloride) 35 187.3-B-[exo-6-m-methoxyphenyl-3-azabicyclo[3.2.0]heptan-3-yl] ethylindole 188.2-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptan-3-yl] methyl-3,4-dihydroquinazolin-4-one 40 189.2-[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-yl]methyl 45 3,4-dihydroquinazolin-4-one 191. 2-[exo-6-m-chloropheny1-3-azabicyc1o[3.2 .Ojheptan-3-yl] methyl-3, 4-dihydroquinazolin-4-one 192. 2-[exo-6-o-methoxyphenyl-3-azabicyclo[ 3 .2 .0]heptan-3-yl] 5 methyl-3, 4-dihydroquinazolin-4-one 193. 2-[exo-6-p-fluoropheny1-3-azabicyclo[3.2.]heptaf 3 yl] methyl-4 -hydroxy-6-methylpyrimidine 10 194. 6-[exo-6-p-fluorophefyly-3-azabicyclo[3.2.0]heptaf3ylP methyl-2 -methyl-4 -hydroxypyrimidine 195. 6-[exo-6-p-fluorophenyl-3-azabicyc1o[3.2.O]heptafl3-yl] methyluracil 15 196. 6-[exo-6-pheny1-3-azabicyclo[3.2.]heptaf3y1]methylN uracil 197. 6-[exo-6-p-fluorophefyl-3-azabicyclo[3.2.O]heptafl 3 -yl] 20 1,2,3, 4-tetrahydro-1, 3-dimethyl-2, 4-dioxopyrimidine 198.5 -eo6pfurpey-3aaiyl[..]etn 3-yl ]ethyl-i, 2,3, 4-tetrahydro-6-methyl-2, 4-dioxopyrimidine 25 199.5--eo6pfurpey -zaiyl[..]etn3y] ethyl-i,2,3, 4-tetrahydro-1, 6-dimethyl-2 ,4-dioxopyrimidine 200. 5-J3[exo6-p-fluorophenyl-3-azabicyclo[3.2.]heptaf 3 yl] ethyl-i, 2,3, 4-tetrahydro-3, 6-dimethyl-2 ,4-dioxopyrimidine 30 201. 5-13[exo6-p-fluorophenyl-3-azabicyclo[3.2.O]heptafl 3 -yl] ethyl-i, 2,3, 4-tetrahydro-3, 6-dimethyl-2 ,4-dithiopyrimidine 202.5--eo6pfurpey -zaiyl[..]etn3y] 35 ethyl-i, 2,3, 4-tetrahydro-i, 3, 6-trimethyl-2 ,4-dioxopyrimidine 203.5--eo6pfurpey -zaiyl[..]etn3y] ethyl-i, 2,3, 4-tetrahydro-6-amino-i-methyl- 2 ,4-dioxo pyrimidine 40 204.5--eo6pfurpey -zaiyl[..]etn3y] ethyl-2 -amino-6-methyl-4 (3H )pyrimidinone 205.5--eo6pfurpey -zaiyl[..]etn3yl 45 ethyl-2-amino-3, 6-dimethyl-4 (3H )pyrimidinone 19 206. 5-B-[exo-6-p-fluoropheny1-3-azabicyc1o[3.2.]heptal-3-y1] ethyl-2-methylamino-3, 6-dimethyl-4 (3H )pyrimidinone 207. 5-B-[exo-6-p-fluorophenyl-3-azabicyclof 3.2 .0]heptan-3-yl] 5 ethyl-2-methylamino-3-ethyl-6-methyl-4 (3H )pyrimidinone 208. 5-j3-[exo-6-p-fuoropheny-3-azabicyclo[3.2.0]heptaf-3ylV ethyl-2-amino-3-ethyl-6-methyl-4 (3H )pyrimidinone 10 209. 5-B-[exo-6-p-chlorophenyl-3-azabicycla[3.2.0]heptan-3-y1] ethyl-2-methylamino-3 ,6-dimethyl-4 (3H )pyrimidinone 210. 5-B-[exo-6-m-chlorophenyl-3-azabicyclo[3.2.0]heptafl-3-yl] ethyl-2-methylamino-3, 6-dimethyl-4 (3H )pyrimidinone 211. 5-B3-[exo-6-o-fluorophenyl-3-azabicyclo[3.2.0]heptafl-3-yl] ethyl-2-methylamino-3, 6-dimethyl-4 (3H)pyrimidinone 212. 5-B-[exo-6-p-trifluoromethylphefl-3-azabicyc1o[3 .2.0] 20 heptan-3-yl]ethyl-2-methylamilo-3, 6-dimethyl-4 (3H) pyrimidinone 213. 5-1-[exo-6-p-cyanophenyl-3-azabicyclo[ 3.2 .0]heptan 3-yl ]ethyl-2-methylamino-3, 6-dimethyl-4 (3H )pyrimidinone 25 214. 5-1-[exo-6-m-fluorophenyl-3-azabicyclo[3 .2 .0]heptan 3-yl ]ethyl-2-methylamino-3, 6-dimethyl-4 (3H )pyrimidinone 215. 5-1-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptal 30 3-yl ]ethyl-2-methylamino-4-methoxy-6-methylpyriidile 216. 3-f-[exo-6-pheny-7-methy-1,5-cis-3,7-diazabicyclo[3.3.OV octan-3-yl]ethyl-2, 4-( 1H, 3H)quinazolinedione 35 21.3p[no6pey--ehl15cs37daaiyl[..] octan-3-yl]ethyl-2, 4-( 1H,3H)quinazolinedione 218. 3-I3[exo-6-p-fluorophenyl-7-methy1-1, 5-cis-3, 7-diazabicyclo [3.3 .0] octan-3-yl ]ethyl-2 ,4- ( H, 3H )quinazolinedione 40 219. 3-p-[exo-6-p-trifluoromethylphefl-7-methy1-1,5-CiS- 3
,
7 diazabicyclo[3.3.0]octan-3-yl]ethyl-6-fluoro-2,4-(lH, 3
H)
quinazolinedione 45 220.3 -eo6mclrpey--ety-,-i-,-izbcco [3.3.0] octan-3-yl ]ethyl-2 ,4- ( H, 3H )quinazolinedione 20 221. 3-1-[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-j-[exo-6-phenyl-7-methyl-1,5-cis-3,7-diazabicyclo[3.3.O] 5 octan-3-yl]ethyl-2-methylamino-3,6-dimethyl-4 (3H) pyr imidinone 223. 5-p-[exo-6-p-fluoropheny1-7-methy1-1,5-cis-3,7-diazabicyc1o [3.3.0 ]octan-3-yl ]ethyl-2-methylamino-3 ,6-dimethyl 10 4 (3H )pyrimidinone 224. 1-fP-exo-6-p-fluorophenyl-7-methy1-1, 5-cis-3, 7-diazabicyclo [3.3.0 ]octan-3-yl ]ethyl-2 (3H)benzimidazolone 15 225. 5-p-[exo-6-p-nitropheny1-7-methyl-1, 5-cis-3, 7-diazabicyclo [3.3.0 ]octan-3-yl ]ethyl-2-methylanhino-3, 6-dimethyl 4 (3H )pyrimidinone 226. 5-p-[exo-6-phenyl-7-methyl-1,5-CiB-3,7-diazabicyc1o[3.3.0] 20 octan-3-yl]ethyl-2-methylamino-3 ,6-dimethyl-4 (3H) pyrimidinone 227. 5-I0[endo-6-phenyl-7-methyl-1,5-cis-3,7-diazabicyclo[3.3.0] octan-3-yl]ethyl-2-methylanino-3, 6-dimethyl-4 (3H) 25 pyrimidinone 228. 3-p-[exo-6-p-fluorophenyl-7-methy1-1, 5-cis-3 ,7-diazabicyclo [3.3.0]octan-3-yl]ethyl-2-methyl-4H-pyrido[l.2-a] pyrimidin-4 -one 30 229. 1-fp-[exo-6-p-fluorophenyl-7-methyl-1, 5-cis-3,7-diazabicyclo [3.3.0] octan-3-yl ]ethylindolin-2-one 230. 6-p-[exo-6-p-fluorophenyl-7-methy1-1, 5-cis-3,7-diazabicyclo 35 [3.3.0]octan-3-yl]ethyl-7-methyl-5H-thiazolo[3.2-a] pyrimidin-5-one 231. 1-p-[exo-6-p-fluorophenyl-7-methy1-1,5-Cis-3,7-diazabicyc1o [3.3.0] octan-3-yl ]ethyl-2 ( H )quinolone 40 232. 3-p-[7-pheny1-1,5-cis-3,7-diazabicyclo[3.3.0]octal-3-y1] ethyl-2, 4- ( H, 3H )quinazolinedione 233. 3-p-[7-p-fluorophenyl-1,5-cis-3,7-diazabicyclo[3.3.0] 45 octan-3-yl]ethyl-2, 4-( 1H,3H)quinazolinedione 21 234. 5-p-[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-p-[exo-6-p-fluorophenyl-3-azabicyclo[3.1.0]hexan-3-yl] 5 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 10 237.3-p-[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 15 239. 6-p-[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-p-[6-p-fluorophenyl-1,5-cis-3-azabicyclo[3.3.0]oct-6 20 en-3-yl]ethyl-2,4-(1H,3H)quinazolinedione 241. 5-p-[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 25 242. 6-p-[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-p-[6-phenyl-1,5-cis-3-azabicyclo[3.3.0]oct-6-en-3-yl] ethyl-2(3H)benzimidazolone 30 244. 1-p-[6-p-fluorophenyl-1,5-cis-3-azabicyclo[3.3.0]oct-6 en-3-yl]ethylindolin-2-one 245. 1-p-[6-p-fluorophenyl-1,5-cis-3-azabicyclo[3.3.0]oct-6 35 en-3-yl]ethyl-2(1H)quinolone 246. 3-p-[exo-6-p-fluorophenyl-1,5-cis-3-azabicyclo[3.3.0]octan 3-yl]ethyl-2,4-(1H,3H)quinazolinedione 40 247. 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-p-[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 45 22 249. 1-P-(exo-6-p-fluoropheny1-1,5-cis-3-azabicyclo(3.3.0]octan 3-yl Iethylindolin-2 -one 250. 1-f-[exo-6-p-fluorophenyl-1,5-cis-3-azabicyclo[3.3.Oloctan 5 3-yllethyl-2( 1H)quinolone 251. 3-p-[endo-6-p-fluoropheny1-1,5-cis-3-azabicyclo[3.3.O]octal 3-yl ]ethyl-2, 4- ( H,3H )quinazolinedione 10 252. 5-f-[endo-6-p-fluorophenyl-1,5-cis-3-azabicyclo[3.3.0octal 3-yl]ethyl-2-methylamino-3, 6-dimethyl-4 (3H)pyrimidinone 253. 6-p-[endopheny1-1,5-cis-3-azabicyclo[3.3.O]octan-3-y1] ethyl-7-methyl-5H-thiazolo[3 .2-a]pyrimidin-5-one 15 254. 1-t-[endo-6-p-fluorophenyl-1,5-cis-3-azabicyclo[3.3.0]octa1 3-yl ]ethylindolin-2-one 255. 1-43-[endo-6-p-fluorophenyl-1,5-cis-3-azabicyclo[3.3.O]octal 20 3-yl ]ethyl-2 ( H)quinolone 256. 3-.j-[exo-7-p-fluorophenyl-1,5-cis-3-azabicyclo[3.3.0]octal 3-yl]ethyl-2,4-( 1H,3H)quinazolinedione 25 257. 5-p-[exo-7-p-fluoropheny1-1,5-cis-3-azabicyclo[3.3.0]octal 3-yl ]ethyl-2 -methylamino-3, 6-dimethyl-4 (3H )pyrimidinone 258. 6-p-[exo-7-phenyl-1,5-cis-3-azabicyclo[3.3.0Ioctafl-3-y1] ethyl-7-methyl-5H-thiazolo[ 3. 2-a]pyrimidin-5-one 30 259. 1-p-[exo-7-p-fluorophenyl-1,5-cis-3-azabicyclo[3.3.0]octal 3-yl ]ethylindolin-2-one 260. 1-I3-[exo-7-p-fluoropheny1-1,5-cis-3-azabicyclo[3.3.0Ooctal 35 3-yl]ethyl-2( 1H)quinolone 261. 3-p-[endo-6-p-fluorophenyl-1,5-cis-3-azabicyclo[4.3.0]lof 3-yl ]ethyl-2, 4-( 1H, 3H)quinazolinedione 40 262. 5-f-[endo-6-p-fluorophenyl-1,5-cis-3-azabicyclo[4.3.0flof 3-yl ]ethyl-2-niethylaxnino-3, 6-dimethyl-4 (3H)pyrimidinone 263. 3-f-[endo-6-phenyl-1,5-cis-3-azabicyclo[4.3.]lof-3-y1] ethyl-2, 4- ( H, 3H )quinazolinedione 45 23 264. 5-0-[endo-6-phenyl-1,5-cis-3-azabicyclo[4.3.0]nofl-3-y1] ethyl-2-methylamino-3, 6-dimethyl-4 (3H )pyrimidinone 265. 3-j-[endo-6-p-trifluoromethylphenyl-1,5-cis-3-azabicyclo 5 [4.3.O)non-3-yl]ethyl-2,4-(1H,3H)quinazolinedione, 266. 5-1-[endo-6-p-trifluoromethylphenyl-1,5-cis-3-azabicyclo [4.3.O]non-3-yl]ethyl-2-methylamino-3,6-dimethyl-4(3H) pyrimidinone 10 267. 3-p-[endo-6-p-fluorophenyl-1,5-cis-3-azabicyclo[4 .3.O]non 7-en-3-yl]ethyl-2,4-( 1H,3H)guinazolinedione 268. 5-f-[endo-6-p-fluorophenyl-1,5-cis-3-azabicyclo[4.3.O]non 15 7-en-3-yl]ethyl-2-methylamino-3, 6-dimethyl-4(3H) pyrimidinone 269. 1-fp-[endo-6-p-fluorophenyl-1,5-cis-3-azabicyclo[4.3.O]non 7-en-3-yl]ethyl-2 (3H)benzimidazolone 20 270. 1-p-[endo-6-p-fluorophenyl-1,5-cis-3-azabicyc1o4.3.]of 7-en-3-yl Iethylindolin-2-one 271. 3-g-[6-p-fluorophenyl-1,5-cis-3-azabicyclo[4.3.0]lof-6-el 25 3-yl]ethyl-2,4-(1H,3H)quinazolinediole 272. 5-p-[6-p-fluorophenyl-1,5-cis-3-azabicyclo[4.3.O]flon-6-en 3-yl ]ethyl-2-methylamino-3, 6-dimethyl-4 (3H )pyrimidinone 30 273. 3-p-[6-phenyl-1,5-cis-3-azabicyclo[4.3.O]non-6-el-3-y1] ethyl-2, 4- ( H, 3H )quinazolinedione 274. 5-f-[6-phenyl-1,5-cis-3-azabicyclo[4.3.0]non-6-en-3-yl] ethyl-2-methylamino-3 ,6-dimethyl-4 (3H)pyrimidinone 35 275. 3-p-[ 6-p-trifluoromethylphenyl-1, 5-cis-3-azabicyclo [4.3.0]non-6-en-3-yl]ethyl-2,4-( 1H,3H)quinazolinedione 276. 5-p-[6-p-trifluoromethylphenyl-1,5-cis-3-azabicyclo[4.3.O] 40 non-6-en-3-yl]ethyl-2-methylamino-3,6-dimethyl-4( 3H) pyrimidinone 277. 1-fp-[6-p-fluorophenyl-1,5-cis-3-azabicyclo[4.3.0]non-6-el 3-yl Iethyl-2 (3H )benzimidazolone 45 24 278. 1-p-[6-p-fluoropheny1-1,5-cis-3-azabicyc1o4.3.0flof- 6 -el 3-yl ]ethylindolin-2-one 279.1 -6pfurpey-,-i-3aaiyl[..]o--n 5 3-yl ]ethyl-2 ( H )quinolone 280. 3-p-[exo-6-p-fluorophenyl-1,5-cis-3-azabicyc1Q[4.3.]lol 7 en-3-yl]ethyl-2,4-(H,3H)quiazolidofle 10 281.5 -eo6pfurphnl15cs3aabcco430nn7 en-3-yl ]ethyl-2-methylamino-3, 6-dimethyl-4 (3H)pyrimidinone 282.3 -eo6pfurphnl15cs3aabcco430nn7 en-3-yl]ethyl-2-methyl-4H-pyrido[ 1.2-a]pyrimidil-4-ofle 15 283. 1-p-[exo-6-p-fluorophenyl-1,5-cis-3-azabicyc1o[4.3.]ofl7 en-3-yl ]ethyl-2 ( H )quinolone 284.1 -eo6pfurphnl15cs3aabcco430nn7 20 en-3-yl]ethyl-2 (3H)benzimidazolone 285.1 -eo6pfurphnl15cs3aabcco430nn7 en-3-yl ]ethylindolin-2-one 25 286. 3-p-[exo-6-phenyl-1,5-cis-3-azabicyc1o[4.3.0]flof7ef 3 -yl V ethyl-2, 4- ( H, 3H)quinazolinedione 287. 5-j3-[exo-6-pheny1-1,5-cis-3-azabicyc1o[4.3.0]flof-7-ef- 3 yl] ethyl-2-methylamino-3, 6-dimethyl-4 (3H)pyrimidinone 30 288.3 -eo6pfurphnl15cs3aabcco430nn 3-yl]ethyl-2,4-( 1H,3H)quinazolinedione 289. 5-p-[exo-6-p-fluorophehyl-1,5-cis-3-azabicyclo[ 4
.
3 .]lol 35 3-yl ]ethyl-2-methylaiino-3, 6-dimethyl-4 (3H )pyrimidinone 290.3 -eo6pey-,-i--zaiyl[..]o--lehl 2, 4-( 1H, 3H)quinazolinedione 40 291.5p [ x--hnl1 -i--zbcyl[43 nn3y ehl 2-methylamino-3, 6-dimethyl-4 (3H)pyrimidinone 292. 6-p-[exo-6-p-fluorophenyl-1,5-cis-3-azabicyclo4.
3 .]ofl 3-yl]ethyl-7-methyl-5H-thiazolo[3 .2-a]pyrimidin-5-ofle 45 25 293. 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-s-[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 15 298.3-s-[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 20 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 25 301.5-s-[7-phenyl-3-azabicyclo[4.3.0]non-1-en-3-yl]ethyl 2-methylamino-3,6-dimethyl-4(3H)pyrimidinone 302.5-s-[7-p-fluorophenyl-3-azabicyclo[4.3.0]nonl-l-en- 3 -yl] 30 ethyl-2-methylamino-3,6-dimethyl-4(3H)pyrimidinone 303.3-s-[exo-7-p-fluorophenyl-1,5-cis-3-azabicyclo[4.
3 .0]non 3-yl]ethyl-2,4-(1H,3H)quinazolinedione 35 304.5-s-[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 40 306.1-s-[exo-7-p-fluorophenyl-1,5-cis-3-azabicyclo[4.3.0]non 3-yl]ethylindolin-2-one 307.1-s-[exo-7-p-fluorophenyl-1,5-cis-3-azabicyclo[4.3.0]non 45 3-yl]ethyl-2(lH)quinolone 26 308. 3-p-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. 5-4p-[6-p-fluoropheny1-1,5-cis-8-oxa-3,7-diazabicyc1o[3.3.0] 5 oct-6-en-3-yl]ethyl-2-methylamino-3,6-dimethyl-4 (3H) pyrimidinone 310. 3-p-[exo/endo-6-p-fluorophenyl-1, 5-cis-8-oxa-3, 7-diaza bicyclo [3.3.0 ]-octan-3-yl Iethyl-2, 4- ( H,3H )quinazolinedione 10 311. 5-f-[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 15 312. 1-I3[6-p-fluorophenyl-1,5-cis-8-oxa-3,7-diazabicyclo[3.3.0] oct-6-en-3-yl ]ethylindolin-2-one 313. 6-1-[6-phenyl-1,5-cis-8-oxa-3,7-diazabicyclo[3.3.0] oct-6-en-3-yl ]ethyl-7-methyl-5H-thiazolo( 3, 2-a]pyrimidin 20 5-one 314.N-,(2-[exo-6-phenyl-7-methyl-1,5-cis-3,7-diazabicyclo[3.3.0] octan-3-yl ]ethyl) -4-f luorobenzaniide 25 315.N-(2-[endo-6-phenyl-7-methyl-1,5-cis-3,7-diazabicyc1o[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-yl ]ethyl) -4-fluorobenzamide 30 317. 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 35 [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 40 320.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-fluorophelyl-7-mlethyl-1,5 cis-3,7-diazabicyclo[3.3.0]octan-3-yl]butan--ofle 45 27 322. 1-(4-fluorophenyl)-4-[exo-6-p-fluorophenyl-7-methyl-1,5 cis-3,7-diazabicyclo[3.3.0]octan-3-yl]butan-1-ol 323. N-(2-[exo-6-p-fluorophenyl-1,5-cis-3-azabicyclo[4.3.0] 5 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 10 325. 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-ol 15 327.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 20 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 25 330.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 30 332.1-(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 35 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 40 335.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 45 28 337. N-(2-[exo-6-phenyl-1,5-cis-3-azabicyclo[4.3.0non-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] 5 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 10 340. 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-1,5-cis-3-azabicyclo [4.3.0]non-6-en-3-yl]butan-1-ol 15 342. 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 20 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 25 345.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 30 347.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 35 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 40 350.1-(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-l-ol 45 29 352. N-(2-[endo-6-p-fluorophenyl-1,5-cis-3-azabicyclo[4.3.0]non 3-yl]-2-(N-methyl)aminobenzamide 353. N-(2-[endo-6-p-fluorophenyl-1,5-cis-3-azabicyclo[4.3.0]non 5 3-yllethyl)benzamide 354. N-(2-[endo-6-p-fluorophenyl-1,5-ci-3-azabicyclo[4.3.0]non 3-yl]ethyl)-5-chlorothien-2-ylcarboxamide 10 355.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-yl3ethyl)indene-3-carboxamide 15 357.2-(2-[endo-6-p-fluorophenyl-1,5-cis-3-azabicyclo[4.3.0]non 7-en-3-yl]ethyl)naphthalene 358.N-(2-[endo-6-p-fluorophenyl-1,5-cis-3-azabicyclo[4.3.0]non 20 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-yl]ethyl)-2-(N-methyl)aminobenzamide 25 360.N-(2-[endo-6-p-fluorophenyl-1,5-cis-3-azabicyclo[4.3.0]non 7-en-3-yl]ethyl)naphthalene-1-carboxamide 361.1-(2-[exo-7-p-fluorophenyl-1,5-cis-3-azabicyclo[4.3.0]non 8-en-3-yl]ethyl)naphthalene 30 362.1-(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 35 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 40 365.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 45 30 367. 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-ol 371.N-(2-[exo-7-p-fluorophenyl-1,5-cis-3-azabicyclo[4.3.0]non 3-yl]ethyl)-2-(N-methyl)aminobenzamide 15 372.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 20 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 25 375.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 30 377.1-(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 35 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 40 380.1-(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-ol 45 31 382. 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] 5 ethyl )naphthalene-l-carboxanide 384. N-(2-[exo-6-phenyl-1,5-cis-3-azabicyclo[3.3.O]octan-3-yl] ethyl) indene-3-carboxamide 10 385. 1-(2-[endo-6-p-fluorophenyl-1,5-cis-3-azabicyclo[3.3.O]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 15 387. 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]octal-3-ylj 20 ethyl) naphthalene-l-carboxamide 389. 1-(2-[exo-7-p-fluorophenyl-1,5-cis-3-azabicyclo[3.3.O]octan 3-yl ]ethyl )naphthalene 25 390. 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 30 392.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] 35 ethyl )indene-3-carboxamide 394. N-(2-[exo-6-p-fluorophenyl-3-azabicyclo[3.1.0]hexan-3-yl] ethyl) -4-f luorobenzamide 40 395. 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 45 32 397. N-2[x---loohnl3-zbcco310hxn3y ethyl) -3-chloro-1-benzothien-2-y1carboxamide 398.N-2[x--mclrpenl3aaicco310]ea- Vl 5 ethyl) -4-chlorobenzanide 399.1 2 [--loohny -,-i -- x -, -daaiyl[..] oct-6-en-3-yl ]ethyl )naphthalene 10 40.-2[--loohnl15cs8oa37daaiyl[..] oct-6-en-3-yl ]ethyl)benzamide 4Ol.N-(2-[6-pfluoropheyl1,5cis-8oxa3,7-diazabicyclo 33 .0] oct-6-en-3-yl ]ethyl )naphthalene--carboxamlide 15 40. -2[--loohnl15cs8oa37daaiyl[..] oct-6-eri-3-yl ]ethyl) indene-3-carboxamide 403.1 2[x/no6pfurpenl15CB8oa37daa 20 bicyclo[ 3.3 .O]octan-3-yllethyl)laphthalele 404. N-(2-[exo/edo-6p-fluorophefl1,5cis8oxa- 3
,
7 diaza bicyclo [3.3.0 ]octan-3-yl ]ethyl )benzamide 25 405.1 2[-hnl15cs8oa-,-izbcco330ot 6-en-3-yl ]ethyl) naphthalene 40.-2[-hnl15cs8ox-,-izbcco330ot 6-en-3-yl ]ethyl )benzamide 30 407.N-2[x-- loopey -- zbcco[..]etn3y] ethyl )benzosulfonamide 408.N-2[x--hnl3-zbcco320hetn3y~ty) 35 benzosUlfonamide 409.N-2[x-- lorpey -- zbcyl[..]etn 3-yl ]ethyl )-N-methylbenzosulfoflamide 40 410.N-2[x--5clrohe - l--zbiyl[..]etn 3-yl methyl )-4-f luorobenzosulfoflamide 411.3-eo6pfurpey -zbiyl[..]etn3y]l phenoxypropane 45 33 412. 2-[exo-6-p-fluorophenyl-,3-azabicyclo[3.2.0]heptafl 3 -yl]-l-p fluorophenoxyethane 413. 3-[exo-6-p-fluoropheflyl-3-azabicyclo[3.2.O]heptafl3-yl]-l 5 (1-naphthyloxy)propale 414. 3-[exo-6-p-fluoropheny-3-azabicyclo[3.2.]hepta3yl]l-p t-butylphenoxypropane 10 415. 3-[exo-6-p-fluorophenyl-3-azabicyc1o[3.2.O]heptafl 3-yl] -1-p-f luorophenoxypropane 416. N-(2-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.O]heptal 3-yl Iethyl) thiobenzainide 15 417. N-(2-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.O]heptafl3-ylJ ethyl) -4-f luorothiobenzamide 418. N-(2-[exo-6-p-fluorophefyl-3-azabicyclo[3.2.]heptaf3-yl] 20 ethyl) -4-chlorothiobenzamide 419. O-(2-[exo-6-p-fluorophefyl-3azabicyclo[3.2.]heptan 3 yl]V ethyl )benzoate 25 420. O-(2-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.]heptaf3yl] ethyl-4 -fluorobenzoate 421. N-(2-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.0]heptafl 3 -yl] ethyl) -1H-benzo[cd]indol-2-one 30 422.N-2[x---hoopey -zbcco[..]etn3y] ethyl ) - H-benzo [cd] indol-2 -one 423.N-2[x-- loopey--zbcco[..~etn3y] 35 ethyl) -1H-benzo[cd] indol-2-one 424.N-2[x---hoopey -zbcco[..~etn3y] ethyl) -1H-benzo (cd] indol-2-one 40 425.3,-iehll -eo6pfuoohnl3aaiyl[..] heptan-3-yl ]ethyl )indolin-2-one 426.3,-iehll -eo6pcloohnl3aaiyl[..] heptan-3-yl methyl) indolin-2-Qtne 45 34 427. 3,3-dimethyl-l-(2-[exo-6-m-chlorophenyl-3-azabicyclo[3.2.O] heptan-3-yl methyl) indolin-2-one 428. 1-(2-[exo-6-p-chlorophenyl-3-azabicyclo[3.2.O]heptan-3-yl] 5 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 10 430. 2,5-difluoro-N-(2-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.O] heptan-3-yl ]ethyl) benzamide 431. 2-amino-N-(2-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.O] heptan-3-yl ]ethyl )benzamide i5 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 .0]heptan-3-yl] 20 ethyl) -2-methylaminobenzamide 434. N-(2-[exo-6-p-chlorophenyl-3-azabicyclo[3.2.0]heptan-3-yl] ethyl) -2-methylaininobenzamide 25 435. 3-amino-N-(2-[exo-6-p-chlorophenyl-3-azabicyclo[3.2.0]heptan 3-yl methyl )benzaxnide 436. 4-amino-N-(2-[exo-6-p-chlorophenyl-3-azabicyclo[3.2.O]heptan 3-yl ]ethyl )benzamide 30 437. N-(2-[exo-6-p-fluorophenyl-3-azabicyclo[3.2 .O]heptan-3-yl] ethyl) thiophene-2-carboxanide 438. 5-chloro-N-(2-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.O] 35 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 40 440. 5-chloro-N-( 2-[exo-6-( 5-chloro-2-thienyl)-3-azabicyclo [3.2.0] heptan-3-yl ]ethyl) thiophene-2-carboxamide 441. N-(2-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.O]heptan-3-yl] ethyl )benzo[b] furan-2-carboxaiide 45 35 442. 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 15 447. 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] 20 ethyl)cyclopentanecarboxamide 449.N-(2-[exo-6-p-chlorophenyl-3-azabicyclo[3.2.0]heptan-3-yl] ethyl)cyclopentanecarboxamide 25 450.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] 35 ethyl)indole-2-carboxamide 454.N-(2-[exo-6-p-chlorophenyl-3-azabicyclo[3.2.0]heptan-3-yl] ethyl)indole-3-carboxamide 40 455.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 45 36 457. 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 5 azabicyclo[3.2.0]heptane 459. exo-6-p-fluorophenyl-3-[2-(2-naphthyl)ethyl]-3-azabicyclo [3.2.0]heptane 10 460.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 15 462. 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 20 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 25 465.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 30 467.1-(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-ylJ 35 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 40 470.1-(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 45 37 472. 1-(2-[exo-6-p-fluorophenyl-3-azabicyclo[3.2.O)heptal-3-yl] ethyl)spiro[cyclopropane-1' ,3-indolin-2-one] 473. 3,6-dimethyl-2-methylamino-5-[2-(exo-6-(2-flaphthy1)-3-aza 5 bicyclo[ 3.2 .O]heptan-3-yl)ethyl]-3H-pyrimidin-4-ofle 474. 3,6-dimethyl-2-methylamino-5-[2-(exo-6-(1-flaphthy1)-3-aza bicyclo [3.2.0] heptan-3 -yl )ethyl] -3H-pyrimidin-4 -one 10 475. 3,6-dimethyl-2-methylamino-5-[2-(exo-6-(5-chloro 1-naphthyl)-3-azabicyclo[3.2.0]heptafl-3-yl)ethy1]-3H pyrimidin-4 -one 476. 3,6-dimethyl-2-methylamino-5-[2-(exo-6-(6-chloro-2-laphthyl) 15 3-azabicyclo[ 3.2 .0]heptan-3-yl)ethyl]-3H-pyrimidil-4-ofle 477. 3,6-dimethyl-2-methylamino-5-[2-(exo-6-(9-phelathryl)-3 azabicyclo [3.2.0] heptan-3-yl )ethyl] -3H-pyrimidin-4-one 20 478. 7-methyl-6-[2-(exo-6-(2-flaphthyl)-3-azabicyclo[3.2.0]heptan 3-yl )ethyl )-5H-thiazolo[ 3, 2-a~pyrimidin-5-one 479. 3-[2-(exo-6-(2-faphthyl)-3-azabicyclo[3.2.0]heptal3-yl) ethyl] -1H, 3H-quinazoline-2, 4-dione 25 480. 3-[2-(exo-6-(l-naphthyl)-3-azabicyclo[3.2.0]heptan-3-yl) ethyl] -1H, 3H-quinazoline-2 ,4-dione 481.6 loo3[-eo6(-ahhy)3aaiyl[..]etn 30 3-yl )ethyl] -1H, 3H-quinazoline-2, 4-dione 482.3-2(x--5clr--ahhy)3aaiyl[..]etn 3-yl )ethyl ] -H, 3H-quinazoline-2, 4-dione 35 483.3-2(x- Inpthl--zbcco3..]etn3y) ethyl]-2-methyl-4H-pyrido[ 1.2-a]pyrimidin-4-one 484.1 2(x--2npthl--zbcco3..~etn3y) ethyl] -2 ( H )quinolone 40 485.1 2(x--2npthl--zbcco3..]etn3y) ethyl ]indolin-2-one 486.1 2(x--Inpthl--zbcco3..]etn3y) 45 ethyl] -2 (3H )benzimidazolone 38 487. 1-[2-(exo-6-(1-naphthyl)-3-azabicyclo[3.2.O]heptan-3-yl) ethyl ]-3-methyl-2 (3H )benzimidazolone 488. N-[2-(exo-6-(l-naphthyl)-3-azabicyclo[3.2.O]heptan-3-yl) 5 ethyl~benzamide 4 89. N-[ 2 -(exo-6 -(2 -naphthyl) -3 -azabicyclo [3. 2.O0]heptan-3 -yl) ethyl ]benzamide 10 490.1I-[2-(exo-6-(5-chloro-1-naphthyl)-3-azabicyclo[3.2.O] heptan-3-yl )ethyl ]benzamide 491. 3-[2-( 1-naphthyl)ethyl]-exo-6-(1-naphthyl)-3-azabicyclo [3 .2 .0]heptane 15 492. 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) 20 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 [cdl indol-2-one 25 495. 3,3-dimethyl-l-[2-(exo-6-(l-naphthyl)-3-azabicyclo[3.2.O] heptan-3-yl )ethyl 1-1, 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 30 497. 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] 35 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 40 500.N-[2-(exo-6-(1-naphthyl)-3-azabicyclo[3.2.0]heptan-3-yl) ethyl] -4-f luorobenzamide 501.N-[2-(exo-6-(2-naphthyl)-3-azabicyclo[3.2.0]heptan-3-yl) ethyl] -4-nitrobenzamide 45 39 502. N-[2-(exo-6-(6-chloro-2-naphthyl)-3-azabicyclo[3.2.0heptan 3-yl)ethyl]benzamide 503.N-[2-(exo-6-(1-naphthyl)-3-azabicyclo[3.2.0]heptan-3-yl) 5 ethyl]-4-methoxybenzmide 504.N-[2-(exo-6-(2-naphthyl)-3-azabicyclo[3.2.0]heptan-3-yl) ethyl]-4-hydroxybenzamide 10 505.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 15 507. 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 20 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 25 510. 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 30 512.N-[2-(exo-6-(2-naphthyl)-3-azabicyclo[3.2.0}heptan-3-yl) ethyl]isoindolinone 513.(+)-(lS,5R,6S)exo-1-[2-[6-(4-chlorophenyl)-3-azabicyclo 35 [3.2.0]heptan-3-yl]ethyl]-3-methyl-2H-1,3-dihydro benzimidazol-2-one 514.(+)-(lS,5R,6S)exo-1-[2-[6-(4-chlorophenyl)-3-azabicyclo [3.2.0]heptan-3-yl]ethyl]-3-ethyl-2H-1,3-dihydro 40 benzimidazol-2-one 515.(+)-(lS,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 45 40 516. (+)-(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. (+)-(S,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. (+)-(S,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 20 25 30 35 40 45
Claims (3)
1. The use of N-substituted
3-azabicycloalkane derivatives of 5 the formula I R1 10 " HN- (CH2)n- R 2 in which B is a 4-, 5- or 6-membered ring, which may contain a 15 double bond, R 1 is a phenyl, naphthyl, phenanthryl or thienyl group, in each case unsubstituted or mono- or disubstituted by 20 halogen atoms, C 1 . 4 -alkyl, trifluoromethyl, hydroxyl, 0Ci_ 4 -alkoxy, amino, monomethylamino, dimethylamino, cyano or nitro groups, n is the number 0, 1, 2, 3 or 4 and 25 R 2 is a naphthyl group which is unsubstituted or substituted by one or two halogen atoms, or is one of the following radicals: 30R3 0 R 3 - -R 5 , -NR 6 -C-R 7 , -NR 6 -- S 2 R4 35 -N6- ,8 - 0 R8 - R8 40 -O R8 -N O - 00 45 42 N R 9 0 -N R10 -N O 5 R8 N R8 5 N>~~ IR 8 CH3 Ril 10 -N N , NCA N R 9 R> H 3 C N N ' Z 15 0 R 8 0 2 S 0 or N-- - N- O 20 in which R 3 is a hydrogen atom, a hydroxyl group or a phenyl radical which is unsubstituted or substituted by a fluorine, 25 chlorine or bromine atom, R 4 is a hydrogen atom or 30 R 3 and R 4 together are an oxygen atom, R 5 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, 35 C 1 . 4 -alkanoylamino, C 1 . 4 -alkylamino, Ci- 4 -alkyl or methoxy groups, R 6 is a hydrogen atom or a methyl group, 40 R 7 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 C 1 . 4 -alkyl, hydroxyl, 45 methoxy, nitro, cyano, trifluoromethyl, amino or di-Ci. 4 -alkylamino groups, or is a C 3 - 7 -cycloalkyl group, 0050/49558 43 RO is a hydrogen atom or a fluorine or chlorine atom or a C 1 . 4 -alkyl, methoxy or amino group, R 9 is a hydrogen atom or a methyl group and 5 R 10 is a hydrogen atom or a methyl group or R 9 and RIO together with the ring carbon atom are a 10 spirocyclopropane ring, R 11 is a hydrogen atom, a hydroxyl, Cl-C 4 -alkyl or Ci-C 4 -alkoxy group, or together with the adjacent carbon atom is a C-0 or C-S group, 15 X and Y are carbon atoms, CH, CH 2 , NH or CI-C 4 -alkyl-N groups or nitrogen atoms, 20 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 Cl-C 4 -alkoxy group or by a halogen atom, and 25 A is a hydrogen atom, a hydroxyl, amino, mercapto, Ci-C 4 -alkylamino, di-Ci-C 4 -alkylamino, Cl-C 4 -alkylthio or C 1 -C 4 -alkoxy group or together with the adjacent carbon atom is a C=O group or 30 A is a Y-bonded C 3 -C4-alkylene group which may contain one or two non-cumulated double bonds and in which one CH or CH 2 group may be replaced by a nitrogen or sulfur atom or an NH or N-CH 3 group and where the ring is either monosubstituted by a fluorine or chlorine atom or a 35 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, nitro, hydroxyl, methoxy, amino, monomethyl or dimethylamino groups, 40 and in which the X-, Y- and Z-containing ring at the nitrogen atom No. 1 may carry a CI-C 4 -alkyl, allyl or benzyl group and may contain 1 to 3 non-cumulated double bonds, 45 44 and their salts with physiologically acceptable acids for preparing medicaments for treating disorders of the central nervous system. 5 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 10 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. 15 20 25 30 35 40 45
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19854147 | 1998-11-24 | ||
| DE19854147A DE19854147A1 (en) | 1998-11-24 | 1998-11-24 | Control of cocaine addiction comprises administration of N-substituted azabicycloalkane derivative |
| 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 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU1775300A true AU1775300A (en) | 2000-06-13 |
Family
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU17753/00A Abandoned AU1775300A (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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| Country | Link |
|---|---|
| EP (1) | EP1133293A1 (en) |
| JP (1) | JP2002530333A (en) |
| KR (1) | KR20010080535A (en) |
| CN (1) | CN1328455A (en) |
| AR (1) | AR021502A1 (en) |
| AU (1) | AU1775300A (en) |
| BG (1) | BG105549A (en) |
| BR (1) | BR9915589A (en) |
| CA (1) | CA2352526A1 (en) |
| CZ (1) | CZ20011796A3 (en) |
| DE (1) | DE19854147A1 (en) |
| HK (1) | HK1040933A1 (en) |
| HR (1) | HRP20010472A2 (en) |
| HU (1) | HUP0104416A3 (en) |
| IL (1) | IL143181A0 (en) |
| NO (1) | NO20012538L (en) |
| PL (1) | PL348758A1 (en) |
| SK (1) | SK7112001A3 (en) |
| TR (1) | TR200101476T2 (en) |
| WO (1) | WO2000030639A1 (en) |
| ZA (1) | ZA200103976B (en) |
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| BRPI0519013A2 (en) | 2004-12-13 | 2009-11-03 | Lilly Co Eli | single compound or stereoisomers, mixtures of pharmaceutically acceptable stereoisomers, salts, tautomers or prodrugs thereof, pharmaceutical composition, and use of a compound |
| GB0812310D0 (en) | 2008-07-03 | 2008-08-13 | Syngenta Ltd | Novel herbicides |
| MX379289B (en) * | 2013-01-15 | 2025-03-10 | Novartis Ag | USE OF ALPHA 7 NICOTINIC ACETYLCHOLINE RECEPTOR AGONISTS. |
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| AU2717288A (en) * | 1987-11-12 | 1989-06-01 | American Home Products Corporation | Polycyclicamines with psychotropic activity |
| DE4427648A1 (en) * | 1994-08-04 | 1996-02-08 | Basf Ag | N-Stubstituted 3-azabicyclo [3,2,0,] heptane derivatives, their preparation and use |
| DE4341403A1 (en) * | 1993-12-04 | 1995-06-08 | Basf Ag | N-substituted 3-azabicycloalkane derivatives, their preparation and use |
| DE4427647A1 (en) * | 1994-08-04 | 1996-02-08 | Basf Ag | N-substituted azabicycloheptane derivatives, their preparation and use |
-
1998
- 1998-11-24 DE DE19854147A patent/DE19854147A1/en not_active Withdrawn
-
1999
- 1999-11-12 CA CA002352526A patent/CA2352526A1/en not_active Abandoned
- 1999-11-12 IL IL14318199A patent/IL143181A0/en unknown
- 1999-11-12 HU HU0104416A patent/HUP0104416A3/en unknown
- 1999-11-12 AU AU17753/00A patent/AU1775300A/en not_active Abandoned
- 1999-11-12 BR BR9915589-3A patent/BR9915589A/en not_active IP Right Cessation
- 1999-11-12 EP EP99960974A patent/EP1133293A1/en not_active Withdrawn
- 1999-11-12 WO PCT/EP1999/008734 patent/WO2000030639A1/en not_active Application Discontinuation
- 1999-11-12 KR KR1020017006445A patent/KR20010080535A/en not_active Application Discontinuation
- 1999-11-12 SK SK711-2001A patent/SK7112001A3/en unknown
- 1999-11-12 TR TR2001/01476T patent/TR200101476T2/en unknown
- 1999-11-12 JP JP2000583522A patent/JP2002530333A/en active Pending
- 1999-11-12 CZ CZ20011796A patent/CZ20011796A3/en unknown
- 1999-11-12 PL PL99348758A patent/PL348758A1/en not_active Application Discontinuation
- 1999-11-12 CN CN99813559A patent/CN1328455A/en active Pending
- 1999-11-24 AR ARP990105979A patent/AR021502A1/en unknown
-
2001
- 2001-05-16 ZA ZA200103976A patent/ZA200103976B/en unknown
- 2001-05-23 NO NO20012538A patent/NO20012538L/en not_active Application Discontinuation
- 2001-05-30 BG BG105549A patent/BG105549A/en unknown
- 2001-06-21 HR HR20010472A patent/HRP20010472A2/en not_active Application Discontinuation
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| Publication number | Publication date |
|---|---|
| DE19854147A1 (en) | 2000-05-25 |
| HUP0104416A3 (en) | 2002-11-28 |
| BG105549A (en) | 2001-12-29 |
| IL143181A0 (en) | 2002-04-21 |
| CA2352526A1 (en) | 2000-06-02 |
| CZ20011796A3 (en) | 2002-05-15 |
| WO2000030639A1 (en) | 2000-06-02 |
| HRP20010472A2 (en) | 2003-04-30 |
| EP1133293A1 (en) | 2001-09-19 |
| AR021502A1 (en) | 2002-07-24 |
| NO20012538D0 (en) | 2001-05-23 |
| BR9915589A (en) | 2001-08-07 |
| CN1328455A (en) | 2001-12-26 |
| ZA200103976B (en) | 2002-05-16 |
| JP2002530333A (en) | 2002-09-17 |
| NO20012538L (en) | 2001-07-04 |
| TR200101476T2 (en) | 2001-10-22 |
| PL348758A1 (en) | 2002-06-03 |
| SK7112001A3 (en) | 2001-12-03 |
| HUP0104416A2 (en) | 2002-04-29 |
| HK1040933A1 (en) | 2002-06-28 |
| KR20010080535A (en) | 2001-08-22 |
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