JP2009518357A5 - - Google Patents
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- Publication number
- JP2009518357A5 JP2009518357A5 JP2008543818A JP2008543818A JP2009518357A5 JP 2009518357 A5 JP2009518357 A5 JP 2009518357A5 JP 2008543818 A JP2008543818 A JP 2008543818A JP 2008543818 A JP2008543818 A JP 2008543818A JP 2009518357 A5 JP2009518357 A5 JP 2009518357A5
- Authority
- JP
- Japan
- Prior art keywords
- diaza
- bicyclo
- nonane
- methyl
- pyridazin
- 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
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- -1 selenophenyl Chemical group 0.000 claims 15
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 14
- 239000008194 pharmaceutical composition Substances 0.000 claims 8
- 201000010099 disease Diseases 0.000 claims 7
- 208000035475 disorder Diseases 0.000 claims 7
- 208000002193 Pain Diseases 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 6
- 125000002541 furyl group Chemical group 0.000 claims 6
- 125000000623 heterocyclic group Chemical group 0.000 claims 6
- 125000000168 pyrrolyl group Chemical group 0.000 claims 6
- 125000001544 thienyl group Chemical group 0.000 claims 6
- 125000001475 halogen functional group Chemical group 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 4
- 125000002971 oxazolyl group Chemical group 0.000 claims 4
- 125000003373 pyrazinyl group Chemical group 0.000 claims 4
- 125000002098 pyridazinyl group Chemical group 0.000 claims 4
- 125000004076 pyridyl group Chemical group 0.000 claims 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 4
- 125000000335 thiazolyl group Chemical group 0.000 claims 4
- 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 3
- 208000032131 Diabetic Neuropathies Diseases 0.000 claims 3
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims 3
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 3
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 3
- 125000002527 bicyclic carbocyclic group Chemical group 0.000 claims 3
- 125000002837 carbocyclic group Chemical group 0.000 claims 3
- 125000004966 cyanoalkyl group Chemical group 0.000 claims 3
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 125000002883 imidazolyl group Chemical group 0.000 claims 3
- 125000001041 indolyl group Chemical group 0.000 claims 3
- 125000001786 isothiazolyl group Chemical group 0.000 claims 3
- 125000000842 isoxazolyl group Chemical group 0.000 claims 3
- 125000001624 naphthyl group Chemical group 0.000 claims 3
- 125000003226 pyrazolyl group Chemical group 0.000 claims 3
- 201000000980 schizophrenia Diseases 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- 125000004306 triazinyl group Chemical group 0.000 claims 3
- 125000001425 triazolyl group Chemical group 0.000 claims 3
- 125000004952 trihaloalkoxy group Chemical group 0.000 claims 3
- 208000032841 Bulimia Diseases 0.000 claims 2
- 206010006550 Bulimia nervosa Diseases 0.000 claims 2
- 208000010886 Peripheral nerve injury Diseases 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 125000004183 alkoxy alkyl 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
- 230000006735 deficit Effects 0.000 claims 2
- 125000001188 haloalkyl group Chemical group 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 239000000203 mixture Substances 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
- 239000000126 substance Substances 0.000 claims 2
- 208000011580 syndromic disease Diseases 0.000 claims 2
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims 1
- FGOQONPFPVZWHX-UHFFFAOYSA-N 2-(4-chlorophenyl)-5-(9-methyl-3,9-diazabicyclo[3.3.1]nonan-3-yl)-1,3,4-thiadiazole Chemical compound CN1C(C2)CCCC1CN2C(S1)=NN=C1C1=CC=C(Cl)C=C1 FGOQONPFPVZWHX-UHFFFAOYSA-N 0.000 claims 1
- IDISALVIHFLVGH-UHFFFAOYSA-N 2-(9-methyl-3,9-diazabicyclo[3.3.1]nonan-3-yl)-5-phenyl-1,3,4-thiadiazole Chemical compound CN1C(C2)CCCC1CN2C(S1)=NN=C1C1=CC=CC=C1 IDISALVIHFLVGH-UHFFFAOYSA-N 0.000 claims 1
- XSQQPNAJQNHRDG-UHFFFAOYSA-N 3-(6-phenylpyridazin-3-yl)-3,9-diazabicyclo[3.3.1]nonane Chemical compound C1C(N2)CCCC2CN1C(N=N1)=CC=C1C1=CC=CC=C1 XSQQPNAJQNHRDG-UHFFFAOYSA-N 0.000 claims 1
- CYNAMJOAZBZKAX-UHFFFAOYSA-N 3-(6-phenylpyridazin-3-yl)-9-propan-2-yl-3,9-diazabicyclo[3.3.1]nonane Chemical compound CC(C)N1C(C2)CCCC1CN2C(N=N1)=CC=C1C1=CC=CC=C1 CYNAMJOAZBZKAX-UHFFFAOYSA-N 0.000 claims 1
- VUWLIVJBMFYYTA-UHFFFAOYSA-N 3-[5-(1-benzofuran-2-yl)pyrimidin-2-yl]-9-methyl-3,9-diazabicyclo[3.3.1]nonane Chemical compound C1=CC=C2OC(C3=CN=C(N=C3)N3CC4CCCC(C3)N4C)=CC2=C1 VUWLIVJBMFYYTA-UHFFFAOYSA-N 0.000 claims 1
- KEMGSELFJOETLU-UHFFFAOYSA-N 3-[5-(1h-indol-5-yl)pyrimidin-2-yl]-9-methyl-3,9-diazabicyclo[3.3.1]nonane Chemical compound C1=C2NC=CC2=CC(C2=CN=C(N=C2)N2CC3CCCC(C2)N3C)=C1 KEMGSELFJOETLU-UHFFFAOYSA-N 0.000 claims 1
- IKRUSLRJFTUYHB-UHFFFAOYSA-N 3-[5-(furan-2-yl)pyrimidin-2-yl]-9-methyl-3,9-diazabicyclo[3.3.1]nonane Chemical compound CN1C(C2)CCCC1CN2C(N=C1)=NC=C1C1=CC=CO1 IKRUSLRJFTUYHB-UHFFFAOYSA-N 0.000 claims 1
- DHFHVVFDTGXXGW-UHFFFAOYSA-N 3-[5-(furan-3-yl)pyrimidin-2-yl]-9-methyl-3,9-diazabicyclo[3.3.1]nonane Chemical compound CN1C(C2)CCCC1CN2C(N=C1)=NC=C1C=1C=COC=1 DHFHVVFDTGXXGW-UHFFFAOYSA-N 0.000 claims 1
- PUYRDTPXVOXEAZ-UHFFFAOYSA-N 3-[6-(1,3-benzodioxol-5-yl)pyridazin-3-yl]-9-methyl-3,9-diazabicyclo[3.3.1]nonane Chemical compound C1=C2OCOC2=CC(C2=CC=C(N=N2)N2CC3CCCC(C2)N3C)=C1 PUYRDTPXVOXEAZ-UHFFFAOYSA-N 0.000 claims 1
- RMBARHWXTKPXTF-UHFFFAOYSA-N 3-[6-(1-benzofuran-2-yl)pyridazin-3-yl]-9-methyl-3,9-diazabicyclo[3.3.1]nonane Chemical compound C1=CC=C2OC(C3=CC=C(N=N3)N3CC4CCCC(C3)N4C)=CC2=C1 RMBARHWXTKPXTF-UHFFFAOYSA-N 0.000 claims 1
- VZYSWDFEPJQXTQ-UHFFFAOYSA-N 3-[6-(1-benzothiophen-2-yl)pyridazin-3-yl]-9-methyl-3,9-diazabicyclo[3.3.1]nonane Chemical compound C1=CC=C2SC(C3=CC=C(N=N3)N3CC4CCCC(C3)N4C)=CC2=C1 VZYSWDFEPJQXTQ-UHFFFAOYSA-N 0.000 claims 1
- OHRXMAVNLQVSHQ-UHFFFAOYSA-N 3-[6-(1h-indol-5-yl)pyridazin-3-yl]-9-methyl-3,9-diazabicyclo[3.3.1]nonane Chemical compound C1=C2NC=CC2=CC(C2=CC=C(N=N2)N2CC3CCCC(C2)N3C)=C1 OHRXMAVNLQVSHQ-UHFFFAOYSA-N 0.000 claims 1
- KKYYDKUWGOVCGA-UHFFFAOYSA-N 3-[6-(2,3-difluorophenyl)pyridazin-3-yl]-9-methyl-3,9-diazabicyclo[3.3.1]nonane Chemical compound CN1C(C2)CCCC1CN2C(N=N1)=CC=C1C1=CC=CC(F)=C1F KKYYDKUWGOVCGA-UHFFFAOYSA-N 0.000 claims 1
- XSGLPUSPWSLWGK-UHFFFAOYSA-N 3-[6-(2,3-dihydro-1,4-benzodioxin-6-yl)pyridazin-3-yl]-9-methyl-3,9-diazabicyclo[3.3.1]nonane Chemical compound O1CCOC2=CC(C3=CC=C(N=N3)N3CC4CCCC(C3)N4C)=CC=C21 XSGLPUSPWSLWGK-UHFFFAOYSA-N 0.000 claims 1
- YZFUYFPDFPMBDN-UHFFFAOYSA-N 3-[6-(2,3-dimethoxyphenyl)pyridazin-3-yl]-9-methyl-3,9-diazabicyclo[3.3.1]nonane Chemical compound COC1=CC=CC(C=2N=NC(=CC=2)N2CC3CCCC(N3C)C2)=C1OC YZFUYFPDFPMBDN-UHFFFAOYSA-N 0.000 claims 1
- JXUDAISOBGNDHQ-UHFFFAOYSA-N 3-[6-(2-fluorophenyl)pyridazin-3-yl]-9-methyl-3,9-diazabicyclo[3.3.1]nonane Chemical compound CN1C(C2)CCCC1CN2C(N=N1)=CC=C1C1=CC=CC=C1F JXUDAISOBGNDHQ-UHFFFAOYSA-N 0.000 claims 1
- XFXGDPHXKMDYST-UHFFFAOYSA-N 3-[6-(2-methoxyphenyl)pyridazin-3-yl]-9-methyl-3,9-diazabicyclo[3.3.1]nonane Chemical compound COC1=CC=CC=C1C1=CC=C(N2CC3CCCC(N3C)C2)N=N1 XFXGDPHXKMDYST-UHFFFAOYSA-N 0.000 claims 1
- OJZHWYNIPYNESI-UHFFFAOYSA-N 3-[6-(3,4-difluorophenyl)pyridazin-3-yl]-9-methyl-3,9-diazabicyclo[3.3.1]nonane Chemical compound CN1C(C2)CCCC1CN2C(N=N1)=CC=C1C1=CC=C(F)C(F)=C1 OJZHWYNIPYNESI-UHFFFAOYSA-N 0.000 claims 1
- IOENKEPDMCPFPM-UHFFFAOYSA-N 3-[6-(3,4-dimethoxyphenyl)pyridazin-3-yl]-9-methyl-3,9-diazabicyclo[3.3.1]nonane Chemical compound C1=C(OC)C(OC)=CC=C1C1=CC=C(N2CC3CCCC(N3C)C2)N=N1 IOENKEPDMCPFPM-UHFFFAOYSA-N 0.000 claims 1
- BIOCLXADHCTJJA-UHFFFAOYSA-N 3-[6-(3-chlorophenyl)pyridazin-3-yl]-9-methyl-3,9-diazabicyclo[3.3.1]nonane Chemical compound CN1C(C2)CCCC1CN2C(N=N1)=CC=C1C1=CC=CC(Cl)=C1 BIOCLXADHCTJJA-UHFFFAOYSA-N 0.000 claims 1
- SHZQLOVONNAGPP-UHFFFAOYSA-N 3-[6-(3-fluorophenyl)pyridazin-3-yl]-9-methyl-3,9-diazabicyclo[3.3.1]nonane Chemical compound CN1C(C2)CCCC1CN2C(N=N1)=CC=C1C1=CC=CC(F)=C1 SHZQLOVONNAGPP-UHFFFAOYSA-N 0.000 claims 1
- PYOUOBGQJNWMCN-UHFFFAOYSA-N 3-[6-(3-methoxyphenyl)pyridazin-3-yl]-9-methyl-3,9-diazabicyclo[3.3.1]nonane Chemical compound COC1=CC=CC(C=2N=NC(=CC=2)N2CC3CCCC(N3C)C2)=C1 PYOUOBGQJNWMCN-UHFFFAOYSA-N 0.000 claims 1
- ODYJYCSNOBKQJA-UHFFFAOYSA-N 3-[6-(4-chlorophenyl)pyridazin-3-yl]-9-methyl-3,9-diazabicyclo[3.3.1]nonane Chemical compound CN1C(C2)CCCC1CN2C(N=N1)=CC=C1C1=CC=C(Cl)C=C1 ODYJYCSNOBKQJA-UHFFFAOYSA-N 0.000 claims 1
- IJEACVLCQBWHBA-UHFFFAOYSA-N 3-[6-(4-fluorophenyl)pyridazin-3-yl]-9-methyl-3,9-diazabicyclo[3.3.1]nonane Chemical compound CN1C(C2)CCCC1CN2C(N=N1)=CC=C1C1=CC=C(F)C=C1 IJEACVLCQBWHBA-UHFFFAOYSA-N 0.000 claims 1
- UFPXNUQARADVFM-UHFFFAOYSA-N 3-[6-(4-methoxyphenyl)pyridazin-3-yl]-9-methyl-3,9-diazabicyclo[3.3.1]nonane Chemical compound C1=CC(OC)=CC=C1C1=CC=C(N2CC3CCCC(N3C)C2)N=N1 UFPXNUQARADVFM-UHFFFAOYSA-N 0.000 claims 1
- KVDZBHUCZJIWTJ-UHFFFAOYSA-N 3-[6-(5-chlorothiophen-2-yl)pyridazin-3-yl]-9-methyl-3,9-diazabicyclo[3.3.1]nonane Chemical compound CN1C(C2)CCCC1CN2C(N=N1)=CC=C1C1=CC=C(Cl)S1 KVDZBHUCZJIWTJ-UHFFFAOYSA-N 0.000 claims 1
- VZOUJCBJYJVQBQ-UHFFFAOYSA-N 3-[6-(9-methyl-3,9-diazabicyclo[3.3.1]nonan-3-yl)pyridazin-3-yl]aniline Chemical compound CN1C(C2)CCCC1CN2C(N=N1)=CC=C1C1=CC=CC(N)=C1 VZOUJCBJYJVQBQ-UHFFFAOYSA-N 0.000 claims 1
- QNFKEPYFXNMHBG-UHFFFAOYSA-N 3-[6-(furan-2-yl)pyridazin-3-yl]-9-methyl-3,9-diazabicyclo[3.3.1]nonane Chemical compound CN1C(C2)CCCC1CN2C(N=N1)=CC=C1C1=CC=CO1 QNFKEPYFXNMHBG-UHFFFAOYSA-N 0.000 claims 1
- IQHDJOUFKKIVFV-UHFFFAOYSA-N 3-[6-(furan-3-yl)pyridazin-3-yl]-9-methyl-3,9-diazabicyclo[3.3.1]nonane Chemical compound CN1C(C2)CCCC1CN2C(N=N1)=CC=C1C=1C=COC=1 IQHDJOUFKKIVFV-UHFFFAOYSA-N 0.000 claims 1
- JFWZGJMWQOKJMP-UHFFFAOYSA-N 9-(2-methoxyethyl)-3-(6-phenylpyridazin-3-yl)-3,9-diazabicyclo[3.3.1]nonane Chemical compound COCCN1C(C2)CCCC1CN2C(N=N1)=CC=C1C1=CC=CC=C1 JFWZGJMWQOKJMP-UHFFFAOYSA-N 0.000 claims 1
- JRHLBFCRXCSEPV-UHFFFAOYSA-N 9-methyl-3-(5-naphthalen-2-ylpyrimidin-2-yl)-3,9-diazabicyclo[3.3.1]nonane Chemical compound C1=CC=CC2=CC(C3=CN=C(N=C3)N3CC4CCCC(C3)N4C)=CC=C21 JRHLBFCRXCSEPV-UHFFFAOYSA-N 0.000 claims 1
- GAJASBATEWQDPZ-UHFFFAOYSA-N 9-methyl-3-(5-phenylpyrimidin-2-yl)-3,9-diazabicyclo[3.3.1]nonane Chemical compound CN1C(C2)CCCC1CN2C(N=C1)=NC=C1C1=CC=CC=C1 GAJASBATEWQDPZ-UHFFFAOYSA-N 0.000 claims 1
- UTXORWNBSQBQHP-UHFFFAOYSA-N 9-methyl-3-(5-thiophen-2-ylpyrimidin-2-yl)-3,9-diazabicyclo[3.3.1]nonane Chemical compound CN1C(C2)CCCC1CN2C(N=C1)=NC=C1C1=CC=CS1 UTXORWNBSQBQHP-UHFFFAOYSA-N 0.000 claims 1
- GPYXLWLDRHEQQL-UHFFFAOYSA-N 9-methyl-3-(5-thiophen-3-ylpyrimidin-2-yl)-3,9-diazabicyclo[3.3.1]nonane Chemical compound CN1C(C2)CCCC1CN2C(N=C1)=NC=C1C=1C=CSC=1 GPYXLWLDRHEQQL-UHFFFAOYSA-N 0.000 claims 1
- STSJVLWHJVKQCN-UHFFFAOYSA-N 9-methyl-3-(6-naphthalen-2-ylpyridazin-3-yl)-3,9-diazabicyclo[3.3.1]nonane Chemical compound C1=CC=CC2=CC(C3=CC=C(N=N3)N3CC4CCCC(C3)N4C)=CC=C21 STSJVLWHJVKQCN-UHFFFAOYSA-N 0.000 claims 1
- YBVCONMKJCCKQC-UHFFFAOYSA-N 9-methyl-3-(6-phenylpyridazin-3-yl)-3,9-diazabicyclo[3.3.1]nonane Chemical compound CN1C(C2)CCCC1CN2C(N=N1)=CC=C1C1=CC=CC=C1 YBVCONMKJCCKQC-UHFFFAOYSA-N 0.000 claims 1
- KYCGHQNQAAJCII-UHFFFAOYSA-N 9-methyl-3-(6-thiophen-2-ylpyridazin-3-yl)-3,9-diazabicyclo[3.3.1]nonane Chemical compound CN1C(C2)CCCC1CN2C(N=N1)=CC=C1C1=CC=CS1 KYCGHQNQAAJCII-UHFFFAOYSA-N 0.000 claims 1
- FGMNOBQFMPYCPT-UHFFFAOYSA-N 9-methyl-3-(6-thiophen-3-ylpyridazin-3-yl)-3,9-diazabicyclo[3.3.1]nonane Chemical compound CN1C(C2)CCCC1CN2C(N=N1)=CC=C1C=1C=CSC=1 FGMNOBQFMPYCPT-UHFFFAOYSA-N 0.000 claims 1
- NCKJDGFAVZUBPM-UHFFFAOYSA-N 9-methyl-3-[6-(1h-pyrrol-2-yl)pyridazin-3-yl]-3,9-diazabicyclo[3.3.1]nonane Chemical compound CN1C(C2)CCCC1CN2C(N=N1)=CC=C1C1=CC=CN1 NCKJDGFAVZUBPM-UHFFFAOYSA-N 0.000 claims 1
- GQYYKRWORSNPBS-UHFFFAOYSA-N 9-methyl-3-[6-[3-(trifluoromethyl)phenyl]pyridazin-3-yl]-3,9-diazabicyclo[3.3.1]nonane Chemical compound CN1C(C2)CCCC1CN2C(N=N1)=CC=C1C1=CC=CC(C(F)(F)F)=C1 GQYYKRWORSNPBS-UHFFFAOYSA-N 0.000 claims 1
- ZSLOGSYNSRFQFQ-UHFFFAOYSA-N 9-methyl-3-[6-[4-(trifluoromethyl)phenyl]pyridazin-3-yl]-3,9-diazabicyclo[3.3.1]nonane Chemical compound CN1C(C2)CCCC1CN2C(N=N1)=CC=C1C1=CC=C(C(F)(F)F)C=C1 ZSLOGSYNSRFQFQ-UHFFFAOYSA-N 0.000 claims 1
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| US7687523B2 (en) | 2006-02-10 | 2010-03-30 | Neurosearch A/S | 3-heteroaryl-3,9-diazabicyclo[3.3.1]nonane derivatives as nicotinic acetylcholine receptor agonists |
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| JP2009537599A (ja) | 2006-05-23 | 2009-10-29 | ノイロサーチ アクティーゼルスカブ | 新規８，１０−ジアザ−ビシクロ［４．３．１］デカン誘導体及びそれらの医学的使用 |
| US8314119B2 (en) | 2006-11-06 | 2012-11-20 | Abbvie Inc. | Azaadamantane derivatives and methods of use |
| US20110142758A1 (en) * | 2008-06-10 | 2011-06-16 | Neurosearch A/S | Indolyl-pyridazinyl-diazabicyclononane derivatives in labelled and unlabelled form and their use in diagnostic methods |
| AR072297A1 (es) | 2008-06-27 | 2010-08-18 | Novartis Ag | Derivados de indol-2-il-piridin-3-ilo, composicion farmaceutica que los comprende y su uso en medicamentos para el tratamiento de enfermedades mediadas por la sintasa aldosterona. |
| TWI558398B (zh) | 2009-09-22 | 2016-11-21 | 諾華公司 | 菸鹼乙醯膽鹼受體α７活化劑之用途 |
| EP2619205B1 (en) | 2010-09-23 | 2017-05-17 | AbbVie Bahamas Ltd. | Monohydrate of an azaadamantane derivative |
| US8729263B2 (en) * | 2012-08-13 | 2014-05-20 | Novartis Ag | 1,4-disubstituted pyridazine analogs there of and methods for treating SMN-deficiency-related conditions |
| EP4151627A1 (en) | 2017-06-05 | 2023-03-22 | PTC Therapeutics, Inc. | Compounds for treating huntington's disease |
| BR112020019373A2 (pt) * | 2018-03-27 | 2020-12-29 | Ptc Therapeutics, Inc. | Compostos para o tratamento da doença de hutington |
| CN108658762B (zh) * | 2018-06-12 | 2021-03-02 | 浙江凯普化工有限公司 | 一种脂环邻二酯的合成方法 |
| IL279688B2 (en) | 2018-06-27 | 2025-01-01 | Ptc Therapeutics Inc | Heterocyclic and heteroaryl compounds for the treatment of Huntington's disease |
| KR20210038845A (ko) | 2018-06-27 | 2021-04-08 | 피티씨 테라퓨틱스, 인크. | 헌팅턴병 치료를 위한 헤테로아릴 화합물 |
| CA3139821A1 (en) | 2019-05-13 | 2020-11-19 | Ptc Therapeutics, Inc. | Compounds for treating huntington's disease |
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| US3293251A (en) * | 1966-12-20 | Rearrangement process for j,b-diaza- bicyclo-(j,z,i)-octane derivatives | ||
| US5478939A (en) * | 1994-07-20 | 1995-12-26 | American Cyanamid Company | (R,R) and (S,S) 2,5-diazabicyclo [2,2,1]heptane derivatives |
| KR100589872B1 (ko) | 1997-05-30 | 2006-06-15 | 뉴로서치 에이/에스 | 8-아자비사이클로(3,2,1)옥트-2-엔 유도체 및 이의 제조방법 |
| JP2002502383A (ja) | 1997-05-30 | 2002-01-22 | ニューロサーアチ・アクティーゼルスカブ | ニコチンＡＣｈレセプターに於けるコリン作動性リガンドとしての９−アザビシクロ（３．３．１）ノン−２−エン及びノナン誘導体 |
| FR2786770B1 (fr) | 1998-12-04 | 2001-01-19 | Synthelabo | Derives de 1,4-diazabicyclo[3.2.2.]nonane, leur preparation et leur application en therapeutique |
| EP1147112B1 (en) * | 1999-01-29 | 2003-10-29 | Abbott Laboratories | Diazabicyclic derivatives as nicotinic acetylcholine receptor ligands |
| US7265115B2 (en) * | 1999-01-29 | 2007-09-04 | Abbott Laboratories | Diazabicyclic CNS active agents |
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| EP1289996B1 (en) | 2000-05-25 | 2005-04-06 | Targacept, Inc. | Heteroaryldiazabicycloalkanes as nicotinic cholinergic receptor ligands |
| FR2809732B1 (fr) | 2000-05-31 | 2002-07-19 | Sanofi Synthelabo | DERIVES DE 4(-2-PHENYLTHIAZOL-5-yl)-1,4-DIAZABICYCLO-[3.2.2] NONANE, LEUR PREPARATION ET LEUR APPLICATION ENTHERAPEUTIQUE |
| FR2809731B1 (fr) | 2000-05-31 | 2002-07-19 | Sanofi Synthelabo | Derives de 1,4-diazabicyclo-[3.2.2] nonane-pheylisoxazole, leur preparation et leur application en therapeutique |
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| FR2832713B1 (fr) | 2001-11-23 | 2004-02-13 | Sanofi Synthelabo | Derives de 4-(1,3,4-thiadiazol-2-yl)-1,4-diazabicyclo[3.2.2] nonane, leur preparation et leur application en therapeutique |
| FR2832712B1 (fr) | 2001-11-23 | 2004-02-13 | Sanofi Synthelabo | Derives de 4-(oxadiazol-3-yl)-1,4-diazabicyclo[3.2.2]nonane, leur preparation et leur application en therapeutique |
| MXPA04010966A (es) * | 2002-05-07 | 2005-01-25 | Neurosearch As | Derivados novedosos de biarilo diazabiciclico. |
| EP1562945B1 (en) | 2002-11-11 | 2006-11-15 | Neurosearch A/S | 1,4-diazabicyclo(3,2,2)nonane derivatives, preparation and therapeutical use thereof |
| US7399765B2 (en) * | 2003-09-19 | 2008-07-15 | Abbott Laboratories | Substituted diazabicycloalkane derivatives |
| CA2543710A1 (en) * | 2003-11-03 | 2005-05-12 | Warner-Lambert Company Llc | Novel norepinephrine reuptake inhibitors for the treatment of central nervous system disorders |
| AU2005298693A1 (en) | 2004-10-20 | 2006-05-04 | Neurosearch A/S | Novel diazabicyclic aryl derivatives and their medical use |
| DE602005012722D1 (de) | 2004-11-30 | 2009-03-26 | Neurosearch As | Neuartige diazabicyclische arylderivate als cholinerge liganden |
| JP2008530172A (ja) | 2005-02-16 | 2008-08-07 | ノイロサーチ アクティーゼルスカブ | ジアザ二環系アリール誘導体及びそれらのニコチン様アセチルコリン受容体におけるコリン作動性リガンドとしての使用 |
| JP5052952B2 (ja) * | 2007-05-07 | 2012-10-17 | 東芝機械株式会社 | マイクロレンズ転写成形用ロールの製造方法および製造装置 |
| AR071997A1 (es) * | 2008-06-04 | 2010-07-28 | Bristol Myers Squibb Co | Forma cristalina de 6-((4s)-2-metil-4-(2-naftil)-1,2,3,4-tetrahidroisoquinolin-7-il)piridazin-3-amina |
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