JP2005538187A5 - - Google Patents
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- JP2005538187A5 JP2005538187A5 JP2005502013A JP2005502013A JP2005538187A5 JP 2005538187 A5 JP2005538187 A5 JP 2005538187A5 JP 2005502013 A JP2005502013 A JP 2005502013A JP 2005502013 A JP2005502013 A JP 2005502013A JP 2005538187 A5 JP2005538187 A5 JP 2005538187A5
- Authority
- JP
- Japan
- Prior art keywords
- alkoxy
- group
- alkyl
- octane
- cycloalkoxy
- 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.)
- Pending
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- -1 5,6,7,8-tetrahydro-naphthyl Chemical group 0.000 claims 56
- UANSQQFYKHHDJM-KRWDZBQOSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]naphthalene-1-carboxamide Chemical compound C1=CC=C2C(C(N[C@@H]3C4CCN(CC4)C3)=O)=CC=CC2=C1 UANSQQFYKHHDJM-KRWDZBQOSA-N 0.000 claims 26
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 25
- 125000003367 polycyclic group Chemical group 0.000 claims 24
- 125000005843 halogen group Chemical group 0.000 claims 21
- 125000000623 heterocyclic group Chemical group 0.000 claims 20
- 125000001424 substituent group Chemical group 0.000 claims 20
- 125000003545 alkoxy group Chemical group 0.000 claims 19
- 125000000217 alkyl group Chemical group 0.000 claims 19
- 125000000753 cycloalkyl group Chemical group 0.000 claims 18
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 18
- 125000002950 monocyclic group Chemical group 0.000 claims 18
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 15
- 125000002837 carbocyclic group Chemical group 0.000 claims 14
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims 13
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 10
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 10
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 10
- 125000005113 hydroxyalkoxy group Chemical group 0.000 claims 10
- 125000004858 cycloalkoxyalkyl group Chemical group 0.000 claims 9
- 201000010099 disease Diseases 0.000 claims 9
- 208000035475 disorder Diseases 0.000 claims 9
- 150000003839 salts Chemical class 0.000 claims 9
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 claims 8
- 150000001408 amides Chemical class 0.000 claims 7
- 238000000034 method Methods 0.000 claims 7
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims 7
- 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 claims 7
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims 6
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 6
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims 6
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims 6
- 125000001041 indolyl group Chemical group 0.000 claims 5
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims 4
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims 4
- 206010049119 Emotional distress Diseases 0.000 claims 3
- KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 claims 3
- 125000003368 amide group Chemical group 0.000 claims 3
- 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 claims 3
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 3
- 230000009429 distress Effects 0.000 claims 3
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims 3
- 125000002098 pyridazinyl group Chemical group 0.000 claims 3
- 125000004159 quinolin-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C([H])C(*)=NC2=C1[H] 0.000 claims 3
- 125000004548 quinolin-3-yl group Chemical group N1=CC(=CC2=CC=CC=C12)* 0.000 claims 3
- 125000004549 quinolin-4-yl group Chemical group N1=CC=C(C2=CC=CC=C12)* 0.000 claims 3
- 125000004550 quinolin-6-yl group Chemical group N1=CC=CC2=CC(=CC=C12)* 0.000 claims 3
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 3
- 125000004262 quinoxalin-2-yl group Chemical group [H]C1=NC2=C([H])C([H])=C([H])C([H])=C2N=C1* 0.000 claims 3
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims 3
- 125000004495 thiazol-4-yl group Chemical group S1C=NC(=C1)* 0.000 claims 3
- 125000004496 thiazol-5-yl group Chemical group S1C=NC=C1* 0.000 claims 3
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims 2
- SURCGQGDUADKBL-UHFFFAOYSA-N 2-(2-hydroxyethylamino)-5-nitrobenzo[de]isoquinoline-1,3-dione Chemical compound [O-][N+](=O)C1=CC(C(N(NCCO)C2=O)=O)=C3C2=CC=CC3=C1 SURCGQGDUADKBL-UHFFFAOYSA-N 0.000 claims 2
- FHBQJQOZXLTNAR-UHFFFAOYSA-N 3-(1-azabicyclo[2.2.2]octan-3-yloxy)-1,2-benzothiazole Chemical compound C1=CC=C2C(OC3C4CCN(C3)CC4)=NSC2=C1 FHBQJQOZXLTNAR-UHFFFAOYSA-N 0.000 claims 2
- 208000024827 Alzheimer disease Diseases 0.000 claims 2
- 208000032841 Bulimia Diseases 0.000 claims 2
- 206010006550 Bulimia nervosa Diseases 0.000 claims 2
- 206010010904 Convulsion Diseases 0.000 claims 2
- 206010012735 Diarrhoea Diseases 0.000 claims 2
- 208000012661 Dyskinesia Diseases 0.000 claims 2
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims 2
- 208000002193 Pain Diseases 0.000 claims 2
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims 2
- 125000003828 azulenyl group Chemical group 0.000 claims 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 claims 2
- 150000001875 compounds Chemical class 0.000 claims 2
- 125000004122 cyclic group Chemical group 0.000 claims 2
- 230000006735 deficit Effects 0.000 claims 2
- 229940079593 drug Drugs 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims 2
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims 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 claims 2
- 125000001624 naphthyl group Chemical group 0.000 claims 2
- 230000004770 neurodegeneration Effects 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 239000000126 substance Substances 0.000 claims 2
- 208000011580 syndromic disease Diseases 0.000 claims 2
- 125000000335 thiazolyl group Chemical group 0.000 claims 2
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims 1
- FIDMJKLFOPNZTL-UHFFFAOYSA-N 1-(1-azabicyclo[2.2.2]octan-3-yloxy)benzotriazole Chemical compound N1=NC2=CC=CC=C2N1OC(C1)C2CCN1CC2 FIDMJKLFOPNZTL-UHFFFAOYSA-N 0.000 claims 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 claims 1
- SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 claims 1
- COPKZPSRVDULIN-UHFFFAOYSA-N 2-(1-azabicyclo[2.2.2]octan-3-yloxy)-1,3-benzothiazole Chemical compound C1=CC=C2SC(OC3C4CCN(C3)CC4)=NC2=C1 COPKZPSRVDULIN-UHFFFAOYSA-N 0.000 claims 1
- ONZZUKINKMKNFG-UHFFFAOYSA-N 2-(1-azabicyclo[2.2.2]octan-3-yloxy)-1,3-benzoxazole Chemical compound C1=CC=C2OC(OC3C4CCN(C3)CC4)=NC2=C1 ONZZUKINKMKNFG-UHFFFAOYSA-N 0.000 claims 1
- BXENYFDBSRHICB-UHFFFAOYSA-N 2-(1-azabicyclo[2.2.2]octan-3-yloxy)-3-chloroquinoxaline Chemical compound C1N(CC2)CCC2C1OC1=NC2=CC=CC=C2N=C1Cl BXENYFDBSRHICB-UHFFFAOYSA-N 0.000 claims 1
- YGRYEAVJUADRGH-UHFFFAOYSA-N 2-(1-azabicyclo[2.2.2]octan-3-yloxy)-3-methoxyquinoxaline Chemical compound C1N(CC2)CCC2C1OC1=NC2=CC=CC=C2N=C1OC YGRYEAVJUADRGH-UHFFFAOYSA-N 0.000 claims 1
- BWNSGMZYAPFBRL-UHFFFAOYSA-N 2-(1-azabicyclo[2.2.2]octan-3-yloxy)-5-(2,4-difluorophenyl)-1,3-thiazole Chemical compound FC1=CC(F)=CC=C1C(S1)=CN=C1OC1C(CC2)CCN2C1 BWNSGMZYAPFBRL-UHFFFAOYSA-N 0.000 claims 1
- BQVJZWBRVUEZKU-UHFFFAOYSA-N 2-(1-azabicyclo[2.2.2]octan-3-yloxy)-5-(furan-3-yl)-1,3-thiazole Chemical compound C1CN(C2)CCC1C2OC(S1)=NC=C1C=1C=COC=1 BQVJZWBRVUEZKU-UHFFFAOYSA-N 0.000 claims 1
- VSKHAHUONMJJFL-UHFFFAOYSA-N 2-(1-azabicyclo[2.2.2]octan-3-yloxy)-5-bromo-1,3-thiazole Chemical group S1C(Br)=CN=C1OC1C(CC2)CCN2C1 VSKHAHUONMJJFL-UHFFFAOYSA-N 0.000 claims 1
- KHJZSFUHZDEQIU-UHFFFAOYSA-N 2-(1-azabicyclo[2.2.2]octan-3-yloxy)-5-phenyl-1,3-thiazole Chemical compound C1CN(C2)CCC1C2OC(S1)=NC=C1C1=CC=CC=C1 KHJZSFUHZDEQIU-UHFFFAOYSA-N 0.000 claims 1
- PTPLMYRMZXCHSZ-UHFFFAOYSA-N 2-(1-azabicyclo[2.2.2]octan-3-yloxy)-5-pyridin-3-yl-1,3-thiazole Chemical compound C1CN(C2)CCC1C2OC(S1)=NC=C1C1=CC=CN=C1 PTPLMYRMZXCHSZ-UHFFFAOYSA-N 0.000 claims 1
- WENRZTCKEUNEMA-UHFFFAOYSA-N 2-(1-azabicyclo[2.2.2]octan-3-yloxy)-5-thiophen-2-yl-1,3-thiazole Chemical compound C1CN(C2)CCC1C2OC(S1)=NC=C1C1=CC=CS1 WENRZTCKEUNEMA-UHFFFAOYSA-N 0.000 claims 1
- GCNWMXJESTZDJB-UHFFFAOYSA-N 2-(1-azabicyclo[2.2.2]octan-3-yloxy)-5-thiophen-3-yl-1,3-thiazole Chemical compound C1CN(C2)CCC1C2OC(S1)=NC=C1C=1C=CSC=1 GCNWMXJESTZDJB-UHFFFAOYSA-N 0.000 claims 1
- JVLOHDNSLWPUJF-UHFFFAOYSA-N 2-(1-azabicyclo[2.2.2]octan-3-yloxy)-6-chloro-1,3-benzothiazole Chemical compound C1N(CC2)CCC2C1OC1=NC2=CC=C(Cl)C=C2S1 JVLOHDNSLWPUJF-UHFFFAOYSA-N 0.000 claims 1
- LRQZHEAZRKGYRO-UHFFFAOYSA-N 2-(1-azabicyclo[2.2.2]octan-3-yloxy)quinoline Chemical compound C1=CC=CC2=NC(OC3C4CCN(C3)CC4)=CC=C21 LRQZHEAZRKGYRO-UHFFFAOYSA-N 0.000 claims 1
- AUVDLTULQQPZDF-UHFFFAOYSA-M 2-(1-azabicyclo[2.2.2]octan-3-yloxy)quinoline;carbanylium;iodide Chemical compound [CH3+].[I-].C1=CC=CC2=NC(OC3C4CCN(C3)CC4)=CC=C21 AUVDLTULQQPZDF-UHFFFAOYSA-M 0.000 claims 1
- NVYFUUNOOKTHMV-UHFFFAOYSA-N 2-(1-azabicyclo[2.2.2]octan-3-yloxy)quinoxaline Chemical compound C1=CC=CC2=NC(OC3C4CCN(C3)CC4)=CN=C21 NVYFUUNOOKTHMV-UHFFFAOYSA-N 0.000 claims 1
- RPAIFTHNSMJQGX-UHFFFAOYSA-M 2-(1-azabicyclo[2.2.2]octan-3-yloxy)quinoxaline;carbanylium;iodide Chemical compound [CH3+].[I-].C1=CC=CC2=NC(OC3C4CCN(C3)CC4)=CN=C21 RPAIFTHNSMJQGX-UHFFFAOYSA-M 0.000 claims 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims 1
- ONNLEVOYDBCRKS-UHFFFAOYSA-N 3-(2,3-dihydro-1h-inden-5-yloxy)-1-azabicyclo[2.2.2]octane Chemical compound C1N(CC2)CCC2C1OC1=CC=C2CCCC2=C1 ONNLEVOYDBCRKS-UHFFFAOYSA-N 0.000 claims 1
- OQMAYTGWZKXAME-UHFFFAOYSA-N 3-(5,6,7,8-tetrahydronaphthalen-2-yloxy)-1-azabicyclo[2.2.2]octane Chemical compound C1N(CC2)CCC2C1OC1=CC=C(CCCC2)C2=C1 OQMAYTGWZKXAME-UHFFFAOYSA-N 0.000 claims 1
- UYDJFXWILYZAEM-UHFFFAOYSA-N 3-(6-bromopyridazin-3-yl)oxy-1-azabicyclo[2.2.2]octane Chemical compound N1=NC(Br)=CC=C1OC1C(CC2)CCN2C1 UYDJFXWILYZAEM-UHFFFAOYSA-N 0.000 claims 1
- MCAXDSHKPBDHIW-UHFFFAOYSA-N 3-(6-chloropyridazin-3-yl)oxy-1-azabicyclo[2.2.2]octane Chemical compound N1=NC(Cl)=CC=C1OC1C(CC2)CCN2C1 MCAXDSHKPBDHIW-UHFFFAOYSA-N 0.000 claims 1
- FWJYJIHEZKZYMF-UHFFFAOYSA-N 3-(6-phenylpyridazin-3-yl)oxy-1-azabicyclo[2.2.2]octane Chemical compound C1CN(C2)CCC1C2OC(N=N1)=CC=C1C1=CC=CC=C1 FWJYJIHEZKZYMF-UHFFFAOYSA-N 0.000 claims 1
- HMJIRHSCISEZOV-UHFFFAOYSA-N 3-(6-pyridin-3-ylpyridazin-3-yl)oxy-1-azabicyclo[2.2.2]octane Chemical compound C1CN(C2)CCC1C2OC(N=N1)=CC=C1C1=CC=CN=C1 HMJIRHSCISEZOV-UHFFFAOYSA-N 0.000 claims 1
- BGMCIWWSQXKNSS-UHFFFAOYSA-N 3-(6-thiophen-2-ylpyridazin-3-yl)oxy-1-azabicyclo[2.2.2]octane Chemical compound C1CN(C2)CCC1C2OC(N=N1)=CC=C1C1=CC=CS1 BGMCIWWSQXKNSS-UHFFFAOYSA-N 0.000 claims 1
- WDLZVIQQVWKVEO-UHFFFAOYSA-N 3-(6-thiophen-3-ylpyridazin-3-yl)oxy-1-azabicyclo[2.2.2]octane Chemical compound C1CN(C2)CCC1C2OC(N=N1)=CC=C1C=1C=CSC=1 WDLZVIQQVWKVEO-UHFFFAOYSA-N 0.000 claims 1
- IIDQULJVLLYOIG-UHFFFAOYSA-N 3-[6-(furan-2-yl)pyridazin-3-yl]oxy-1-azabicyclo[2.2.2]octane Chemical compound C1CN(C2)CCC1C2OC(N=N1)=CC=C1C1=CC=CO1 IIDQULJVLLYOIG-UHFFFAOYSA-N 0.000 claims 1
- PYLFURFAUASCCK-UHFFFAOYSA-N 3-[6-(furan-3-yl)pyridazin-3-yl]oxy-1-azabicyclo[2.2.2]octane Chemical compound C1CN(C2)CCC1C2OC(N=N1)=CC=C1C=1C=COC=1 PYLFURFAUASCCK-UHFFFAOYSA-N 0.000 claims 1
- PQKMYDONPUPYNY-UHFFFAOYSA-N 6-(1-azabicyclo[2.2.2]octan-3-yloxy)-2-phenylimidazo[1,2-b]pyridazine Chemical compound C1CN(C2)CCC1C2OC(=NN1C=2)C=CC1=NC=2C1=CC=CC=C1 PQKMYDONPUPYNY-UHFFFAOYSA-N 0.000 claims 1
- KJIFATUUESTGPL-UHFFFAOYSA-N 6-(1-azabicyclo[2.2.2]octan-3-yloxy)quinoline Chemical compound N1=CC=CC2=CC(OC3C4CCN(C3)CC4)=CC=C21 KJIFATUUESTGPL-UHFFFAOYSA-N 0.000 claims 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 1
- 208000030507 AIDS Diseases 0.000 claims 1
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- 208000000103 Anorexia Nervosa Diseases 0.000 claims 1
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- 206010003805 Autism Diseases 0.000 claims 1
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- 108010009685 Cholinergic Receptors Proteins 0.000 claims 1
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
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- 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 claims 1
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- 125000002249 indol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([*])=C([H])C2=C1[H] 0.000 claims 1
- 125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
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- 239000000203 mixture Substances 0.000 claims 1
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- 229960002715 nicotine Drugs 0.000 claims 1
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 claims 1
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2003
- 2003-08-13 PL PL03375533A patent/PL375533A1/xx not_active Application Discontinuation
- 2003-08-13 CA CA002493245A patent/CA2493245A1/en not_active Abandoned
- 2003-08-13 NZ NZ538058A patent/NZ538058A/en not_active IP Right Cessation
- 2003-08-13 AT AT03787742T patent/ATE384720T1/de not_active IP Right Cessation
- 2003-08-13 US US10/522,150 patent/US20050245567A1/en not_active Abandoned
- 2003-08-13 CN CNB038190788A patent/CN100513406C/zh not_active Expired - Fee Related
- 2003-08-13 KR KR1020057002514A patent/KR20050055711A/ko not_active Ceased
- 2003-08-13 WO PCT/DK2003/000538 patent/WO2004016608A1/en not_active Ceased
- 2003-08-13 JP JP2005502013A patent/JP2005538187A/ja active Pending
- 2003-08-13 DE DE60318860T patent/DE60318860T2/de not_active Expired - Lifetime
- 2003-08-13 EP EP08100204A patent/EP1905771A3/en not_active Withdrawn
- 2003-08-13 MX MXPA05001702A patent/MXPA05001702A/es active IP Right Grant
- 2003-08-13 RU RU2005101748/04A patent/RU2323217C2/ru not_active IP Right Cessation
- 2003-08-13 EP EP03787742A patent/EP1532144B1/en not_active Expired - Lifetime
- 2003-08-13 BR BR0313153-0A patent/BR0313153A/pt not_active IP Right Cessation
- 2003-08-13 AU AU2003250322A patent/AU2003250322B2/en not_active Ceased
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2005
- 2005-01-12 IL IL16625405A patent/IL166254A0/xx unknown
- 2005-03-11 NO NO20051264A patent/NO20051264L/no not_active Application Discontinuation
- 2005-03-14 IS IS7742A patent/IS7742A/is unknown
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2008
- 2008-09-08 US US12/206,302 patent/US20090005390A1/en not_active Abandoned