ZA200105835B - Diazabicyclic derivatives as nicotinic acetylcholine receptor ligands. - Google Patents
Diazabicyclic derivatives as nicotinic acetylcholine receptor ligands. Download PDFInfo
- Publication number
- ZA200105835B ZA200105835B ZA200105835A ZA200105835A ZA200105835B ZA 200105835 B ZA200105835 B ZA 200105835B ZA 200105835 A ZA200105835 A ZA 200105835A ZA 200105835 A ZA200105835 A ZA 200105835A ZA 200105835 B ZA200105835 B ZA 200105835B
- Authority
- ZA
- South Africa
- Prior art keywords
- diazabicyclo
- pyridinyl
- chloro
- octane
- heptane
- Prior art date
Links
- 102000019315 Nicotinic acetylcholine receptors Human genes 0.000 title description 6
- 108050006807 Nicotinic acetylcholine receptors Proteins 0.000 title description 6
- 239000003446 ligand Substances 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 74
- IMNFDUFMRHMDMM-UHFFFAOYSA-N anhydrous n-heptane Natural products CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 60
- 239000000126 substance Substances 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 14
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 13
- 208000035475 disorder Diseases 0.000 claims description 12
- 239000003814 drug Substances 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 241000124008 Mammalia Species 0.000 claims description 9
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 230000003957 neurotransmitter release Effects 0.000 claims description 6
- -1 nitro, 5-tetrazolyl Chemical group 0.000 claims description 6
- AVGHIQUXSVAJBC-UHFFFAOYSA-N 1,2-diazabicyclo[2.2.1]heptane Chemical compound C1C2CCN1NC2 AVGHIQUXSVAJBC-UHFFFAOYSA-N 0.000 claims description 5
- 208000024827 Alzheimer disease Diseases 0.000 claims description 4
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 4
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 4
- 125000005097 aminocarbonylalkyl group Chemical group 0.000 claims description 4
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims description 4
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 4
- 206010012289 Dementia Diseases 0.000 claims description 3
- 208000018737 Parkinson disease Diseases 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- USXYDBGSWSSTGE-OCAPTIKFSA-N (1s,5r)-3-(6-chloropyridazin-3-yl)-3,8-diazabicyclo[3.2.1]octane Chemical compound N1=NC(Cl)=CC=C1N1C[C@H](N2)CC[C@H]2C1 USXYDBGSWSSTGE-OCAPTIKFSA-N 0.000 claims description 2
- BQVKPWLMKZFHIT-UHFFFAOYSA-N 2-(6-chloropyridin-3-yl)-2,5-diazabicyclo[2.2.1]heptane Chemical compound C1=NC(Cl)=CC=C1N1C(CN2)CC2C1 BQVKPWLMKZFHIT-UHFFFAOYSA-N 0.000 claims description 2
- ZKTZNDDSSBHWTJ-UHFFFAOYSA-N 3-(6-chloropyrazin-2-yl)-3,8-diazabicyclo[3.2.1]octane Chemical compound ClC1=CN=CC(N2CC3CCC(N3)C2)=N1 ZKTZNDDSSBHWTJ-UHFFFAOYSA-N 0.000 claims description 2
- YOWRIWKBABNICR-UHFFFAOYSA-N 8-(6-chloropyridazin-3-yl)-3,8-diazabicyclo[3.2.1]octane Chemical compound N1=NC(Cl)=CC=C1N1C2CCC1CNC2 YOWRIWKBABNICR-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 2
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 2
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
- 125000004967 formylalkyl group Chemical group 0.000 claims description 2
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 125000005358 mercaptoalkyl group Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000006678 phenoxycarbonyl group Chemical group 0.000 claims description 2
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 2
- 238000002560 therapeutic procedure Methods 0.000 claims description 2
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 claims 18
- 239000000203 mixture Substances 0.000 claims 12
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims 8
- BOMUADPKDXMXIH-UHFFFAOYSA-M 1,3-bis(1-methylquinolin-1-ium-6-yl)urea;methyl sulfate Chemical compound COS([O-])(=O)=O.COS([O-])(=O)=O.C[N+]1=CC=CC2=CC(NC(=O)NC=3C=C4C=CC=[N+](C4=CC=3)C)=CC=C21 BOMUADPKDXMXIH-UHFFFAOYSA-M 0.000 claims 2
- 208000030507 AIDS Diseases 0.000 claims 2
- 208000019901 Anxiety disease Diseases 0.000 claims 2
- 208000011231 Crohn disease Diseases 0.000 claims 2
- 208000030814 Eating disease Diseases 0.000 claims 2
- 208000010228 Erectile Dysfunction Diseases 0.000 claims 2
- 208000019454 Feeding and Eating disease Diseases 0.000 claims 2
- 206010061218 Inflammation Diseases 0.000 claims 2
- 206010026749 Mania Diseases 0.000 claims 2
- 208000019695 Migraine disease Diseases 0.000 claims 2
- 206010036618 Premenstrual syndrome Diseases 0.000 claims 2
- 208000034189 Sclerosis Diseases 0.000 claims 2
- 208000000323 Tourette Syndrome Diseases 0.000 claims 2
- 208000016620 Tourette disease Diseases 0.000 claims 2
- 206010046543 Urinary incontinence Diseases 0.000 claims 2
- 208000022531 anorexia Diseases 0.000 claims 2
- 230000036506 anxiety Effects 0.000 claims 2
- 206010061428 decreased appetite Diseases 0.000 claims 2
- 235000014632 disordered eating Nutrition 0.000 claims 2
- 206010015037 epilepsy Diseases 0.000 claims 2
- 201000001881 impotence Diseases 0.000 claims 2
- 230000002757 inflammatory effect Effects 0.000 claims 2
- 230000004054 inflammatory process Effects 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 230000007074 memory dysfunction Effects 0.000 claims 2
- 230000004770 neurodegeneration Effects 0.000 claims 2
- 230000004112 neuroprotection Effects 0.000 claims 2
- 201000000980 schizophrenia Diseases 0.000 claims 2
- 208000019116 sleep disease Diseases 0.000 claims 2
- 230000005586 smoking cessation Effects 0.000 claims 2
- 201000009032 substance abuse Diseases 0.000 claims 2
- 231100000736 substance abuse Toxicity 0.000 claims 2
- 208000011117 substance-related disease Diseases 0.000 claims 2
- 208000011580 syndromic disease Diseases 0.000 claims 2
- VWVWGINOEMBUOB-HTQZYQBOSA-N (1r,4r)-2-(5,6-dichloropyridin-3-yl)-2,5-diazabicyclo[2.2.2]octane Chemical compound N1([C@]2([H])CC[C@@](NC2)(C1)[H])C1=CN=C(Cl)C(Cl)=C1 VWVWGINOEMBUOB-HTQZYQBOSA-N 0.000 claims 1
- HSOLSMYRWLJLEZ-PSASIEDQSA-N (1r,4r)-2-(5-bromopyridin-3-yl)-2,5-diazabicyclo[2.2.1]heptane Chemical compound C([C@@]1(NC[C@@]2([H])C1)[H])N2C1=CN=CC(Br)=C1 HSOLSMYRWLJLEZ-PSASIEDQSA-N 0.000 claims 1
- XXQBILVDTXLLLR-NXEZZACHSA-N (1r,4r)-2-(5-methoxypyridin-3-yl)-2,5-diazabicyclo[2.2.2]octane Chemical compound N1([C@]2([H])CC[C@@](NC2)(C1)[H])C1=CN=CC(OC)=C1 XXQBILVDTXLLLR-NXEZZACHSA-N 0.000 claims 1
- PJCWGAPXCCOGKP-HUUCEWRRSA-N (1r,4r)-2-(5-phenylmethoxypyridin-3-yl)-2,5-diazabicyclo[2.2.1]heptane Chemical compound C([C@@]1(NC[C@@]2([H])C1)[H])N2C(C=1)=CN=CC=1OCC1=CC=CC=C1 PJCWGAPXCCOGKP-HUUCEWRRSA-N 0.000 claims 1
- MYGNZAWJQQWAFE-GHMZBOCLSA-N (1r,4r)-2-(6-chloro-5-ethynylpyridin-3-yl)-2,5-diazabicyclo[2.2.2]octane Chemical compound N1([C@]2([H])CC[C@@](NC2)(C1)[H])C1=CN=C(Cl)C(C#C)=C1 MYGNZAWJQQWAFE-GHMZBOCLSA-N 0.000 claims 1
- LPMRSAKXONQJPJ-HTQZYQBOSA-N (1r,4r)-2-(6-chloro-5-methylpyridazin-3-yl)-2,5-diazabicyclo[2.2.1]heptane Chemical compound C([C@@]1(NC[C@@]2([H])C1)[H])N2C1=CC(C)=C(Cl)N=N1 LPMRSAKXONQJPJ-HTQZYQBOSA-N 0.000 claims 1
- CGIVAYCVSYBNBO-RKDXNWHRSA-N (1r,4r)-2-(6-chloro-5-methylpyridazin-3-yl)-5-methyl-2,5-diazabicyclo[2.2.1]heptane Chemical compound C([C@@]1(N(C[C@@]2([H])C1)C)[H])N2C1=CC(C)=C(Cl)N=N1 CGIVAYCVSYBNBO-RKDXNWHRSA-N 0.000 claims 1
- KDAZWLLKSUFNTG-NXEZZACHSA-N (1r,4r)-2-(6-chloro-5-methylpyridin-3-yl)-2,5-diazabicyclo[2.2.2]octane Chemical compound N1([C@]2([H])CC[C@@](NC2)(C1)[H])C1=CN=C(Cl)C(C)=C1 KDAZWLLKSUFNTG-NXEZZACHSA-N 0.000 claims 1
- WKMLUGOFDWMYKZ-HTQZYQBOSA-N (1r,4r)-2-(6-chloropyridazin-3-yl)-5-methyl-2,5-diazabicyclo[2.2.1]heptane Chemical compound C([C@@]1(N(C[C@@]2([H])C1)C)[H])N2C1=CC=C(Cl)N=N1 WKMLUGOFDWMYKZ-HTQZYQBOSA-N 0.000 claims 1
- UXIMNPXAWUTMIF-RKDXNWHRSA-N (1r,4r)-2-(6-chloropyridin-3-yl)-2,5-diazabicyclo[2.2.2]octane Chemical compound N1([C@]2([H])CC[C@@](NC2)(C1)[H])C1=CC=C(Cl)N=C1 UXIMNPXAWUTMIF-RKDXNWHRSA-N 0.000 claims 1
- CBTCGPHDIOYTJM-PSASIEDQSA-N (1r,4r)-2-(6-fluoro-5-methylpyridin-3-yl)-2,5-diazabicyclo[2.2.1]heptane Chemical compound C([C@@]1(NC[C@@]2([H])C1)[H])N2C1=CN=C(F)C(C)=C1 CBTCGPHDIOYTJM-PSASIEDQSA-N 0.000 claims 1
- YDTZQKVJVYSCBP-NXEZZACHSA-N (1r,4r)-2-(6-fluoro-5-methylpyridin-3-yl)-2,5-diazabicyclo[2.2.2]octane Chemical compound N1([C@]2([H])CC[C@@](NC2)(C1)[H])C1=CN=C(F)C(C)=C1 YDTZQKVJVYSCBP-NXEZZACHSA-N 0.000 claims 1
- RKBKKRAXHYTUND-RKDXNWHRSA-N (1r,4r)-2-(6-fluoropyridin-3-yl)-2,5-diazabicyclo[2.2.2]octane Chemical compound N1([C@]2([H])CC[C@@](NC2)(C1)[H])C1=CC=C(F)N=C1 RKBKKRAXHYTUND-RKDXNWHRSA-N 0.000 claims 1
- MDWOWXOFKFFTAB-MWLCHTKSSA-N (1r,4r)-2-(6-methylpyridin-3-yl)-2,5-diazabicyclo[2.2.1]heptane Chemical compound C([C@@]1(NC[C@@]2([H])C1)[H])N2C1=CC=C(C)N=C1 MDWOWXOFKFFTAB-MWLCHTKSSA-N 0.000 claims 1
- IKJZJZXKGKENDY-MWLCHTKSSA-N (1r,4r)-2-pyridin-3-yl-2,5-diazabicyclo[2.2.2]octane Chemical compound N1([C@]2([H])CC[C@@](NC2)(C1)[H])C1=CC=CN=C1 IKJZJZXKGKENDY-MWLCHTKSSA-N 0.000 claims 1
- HBMAFIWQQZYQDP-HTQZYQBOSA-N (1r,5r)-3-(5,6-dichloropyridin-3-yl)-3,6-diazabicyclo[3.2.1]octane Chemical compound C([C@]1([H])NC[C@@](C1)(C1)[H])N1C1=CN=C(Cl)C(Cl)=C1 HBMAFIWQQZYQDP-HTQZYQBOSA-N 0.000 claims 1
- NLBYJBDHHSULMA-MWLCHTKSSA-N (1r,5r)-3-(6-chloro-5-ethynylpyridin-3-yl)-3,6-diazabicyclo[3.2.1]octane Chemical compound C([C@]1([H])NC[C@@](C1)(C1)[H])N1C1=CN=C(Cl)C(C#C)=C1 NLBYJBDHHSULMA-MWLCHTKSSA-N 0.000 claims 1
- NSZNGOJYQHWDIQ-NXEZZACHSA-N (1r,5r)-3-(6-chloro-5-methylpyridin-3-yl)-3,6-diazabicyclo[3.2.1]octane Chemical compound C([C@]1([H])NC[C@@](C1)(C1)[H])N1C1=CN=C(Cl)C(C)=C1 NSZNGOJYQHWDIQ-NXEZZACHSA-N 0.000 claims 1
- GNUGDBIZFORQNU-RKDXNWHRSA-N (1r,5r)-3-(6-chloropyridin-3-yl)-3,6-diazabicyclo[3.2.1]octane Chemical compound C([C@]1([H])NC[C@@](C1)(C1)[H])N1C1=CC=C(Cl)N=C1 GNUGDBIZFORQNU-RKDXNWHRSA-N 0.000 claims 1
- YMDKFHPQWHQEFT-NXEZZACHSA-N (1r,5r)-3-(6-fluoro-5-methylpyridin-3-yl)-3,6-diazabicyclo[3.2.1]octane Chemical compound C([C@]1([H])NC[C@@](C1)(C1)[H])N1C1=CN=C(F)C(C)=C1 YMDKFHPQWHQEFT-NXEZZACHSA-N 0.000 claims 1
- XVIQZJBHPINOMT-NXEZZACHSA-N (1r,5r)-3-pyridin-3-yl-3,6-diazabicyclo[3.2.1]octane Chemical compound C([C@]1([H])NC[C@@](C1)(C1)[H])N1C1=CC=CN=C1 XVIQZJBHPINOMT-NXEZZACHSA-N 0.000 claims 1
- BDDBIULBMALEAN-HTQZYQBOSA-N (1r,5r)-6-(5-bromo-6-chloropyridin-3-yl)-3,6-diazabicyclo[3.2.1]octane Chemical compound C([C@@]1(C[C@]2([H])CNC1)[H])N2C1=CN=C(Cl)C(Br)=C1 BDDBIULBMALEAN-HTQZYQBOSA-N 0.000 claims 1
- PVRLCIPGIOMSTL-MWLCHTKSSA-N (1r,5r)-6-(5-ethynyl-6-fluoropyridin-3-yl)-3,6-diazabicyclo[3.2.1]octane Chemical compound C([C@@]1(C[C@]2([H])CNC1)[H])N2C1=CN=C(F)C(C#C)=C1 PVRLCIPGIOMSTL-MWLCHTKSSA-N 0.000 claims 1
- HVFAVMAEHDLGFX-NXEZZACHSA-N (1r,5r)-6-(5-methoxypyridin-3-yl)-3,6-diazabicyclo[3.2.1]octane Chemical compound C([C@@]1(C[C@]2([H])CNC1)[H])N2C1=CN=CC(OC)=C1 HVFAVMAEHDLGFX-NXEZZACHSA-N 0.000 claims 1
- CFKSUCUQIQQPHA-MWLCHTKSSA-N (1r,5r)-6-(6-chloro-5-methylpyridin-3-yl)-3,6-diazabicyclo[3.2.1]octane Chemical compound C([C@@]1(C[C@]2([H])CNC1)[H])N2C1=CN=C(Cl)C(C)=C1 CFKSUCUQIQQPHA-MWLCHTKSSA-N 0.000 claims 1
- FTGNYUNGLWDAOD-PSASIEDQSA-N (1r,5r)-6-(6-chloropyridin-3-yl)-3,6-diazabicyclo[3.2.1]octane Chemical compound C([C@@]1(C[C@]2([H])CNC1)[H])N2C1=CC=C(Cl)N=C1 FTGNYUNGLWDAOD-PSASIEDQSA-N 0.000 claims 1
- RCUIVEFKYGBCPS-PSASIEDQSA-N (1r,5r)-6-(6-fluoropyridin-3-yl)-3,6-diazabicyclo[3.2.1]octane Chemical compound C([C@@]1(C[C@]2([H])CNC1)[H])N2C1=CC=C(F)N=C1 RCUIVEFKYGBCPS-PSASIEDQSA-N 0.000 claims 1
- ZLHFGGWPDZHAJF-MWLCHTKSSA-N (1r,5r)-6-pyridin-3-yl-3,6-diazabicyclo[3.2.1]octane Chemical compound C([C@@]1(C[C@]2([H])CNC1)[H])N2C1=CC=CN=C1 ZLHFGGWPDZHAJF-MWLCHTKSSA-N 0.000 claims 1
- GJVAKOWYUPGMPN-PWSUYJOCSA-N (1r,5s)-4-(6-chloro-5-ethynylpyridin-3-yl)-4,7-diazabicyclo[3.2.1]octane Chemical compound N1([C@@]2([H])C[C@](NC2)(CC1)[H])C1=CN=C(Cl)C(C#C)=C1 GJVAKOWYUPGMPN-PWSUYJOCSA-N 0.000 claims 1
- HOFIEMCFOWCLAI-KOLCDFICSA-N (1r,5s)-4-(6-chloro-5-methylpyridin-3-yl)-4,7-diazabicyclo[3.2.1]octane Chemical compound N1([C@@]2([H])C[C@](NC2)(CC1)[H])C1=CN=C(Cl)C(C)=C1 HOFIEMCFOWCLAI-KOLCDFICSA-N 0.000 claims 1
- OLGUYJHINSBYSV-JGVFFNPUSA-N (1r,5s)-7-(5,6-dichloropyridin-3-yl)-4,7-diazabicyclo[3.2.1]octane Chemical compound C([C@@]1(C[C@@]2([H])CCN1)[H])N2C1=CN=C(Cl)C(Cl)=C1 OLGUYJHINSBYSV-JGVFFNPUSA-N 0.000 claims 1
- WMYOQZRIEFMPDD-JGVFFNPUSA-N (1r,5s)-7-(5-bromo-6-chloropyridin-3-yl)-4,7-diazabicyclo[3.2.1]octane Chemical compound C([C@@]1(C[C@@]2([H])CCN1)[H])N2C1=CN=C(Cl)C(Br)=C1 WMYOQZRIEFMPDD-JGVFFNPUSA-N 0.000 claims 1
- MXMWDEJGOFAQIF-VHSXEESVSA-N (1r,5s)-7-(5-methoxypyridin-3-yl)-4,7-diazabicyclo[3.2.1]octane Chemical compound C([C@@]1(C[C@@]2([H])CCN1)[H])N2C1=CN=CC(OC)=C1 MXMWDEJGOFAQIF-VHSXEESVSA-N 0.000 claims 1
- KFMJQCWVEWEXSI-DTWKUNHWSA-N (1r,5s)-7-(6-chloropyridin-3-yl)-4,7-diazabicyclo[3.2.1]octane Chemical compound C([C@@]1(C[C@@]2([H])CCN1)[H])N2C1=CC=C(Cl)N=C1 KFMJQCWVEWEXSI-DTWKUNHWSA-N 0.000 claims 1
- DOLPRZLBJYAFEQ-VHSXEESVSA-N (1r,5s)-7-(6-fluoro-5-methylpyridin-3-yl)-4,7-diazabicyclo[3.2.1]octane Chemical compound C([C@@]1(C[C@@]2([H])CCN1)[H])N2C1=CN=C(F)C(C)=C1 DOLPRZLBJYAFEQ-VHSXEESVSA-N 0.000 claims 1
- UBKMVKPQYKJIRD-MNOVXSKESA-N (1r,6s)-4-(6-chloro-5-methylpyridin-3-yl)-4,9-diazabicyclo[4.2.1]nonane Chemical compound C([C@@]1(CC[C@](CC2)(N1)[H])[H])N2C1=CN=C(Cl)C(C)=C1 UBKMVKPQYKJIRD-MNOVXSKESA-N 0.000 claims 1
- IMAFPMMJFGWHQM-MNOVXSKESA-N (1r,6s)-4-pyridin-3-yl-4,9-diazabicyclo[4.2.1]nonane Chemical compound C([C@@]1(CC[C@](CC2)(N1)[H])[H])N2C1=CC=CN=C1 IMAFPMMJFGWHQM-MNOVXSKESA-N 0.000 claims 1
- RWOLEIVLXVKUNS-BDAKNGLRSA-N (1r,6s)-9-(5,6-dichloropyridin-3-yl)-4,9-diazabicyclo[4.2.1]nonane Chemical compound N1([C@@]2([H])CC[C@@]1(CCNC2)[H])C1=CN=C(Cl)C(Cl)=C1 RWOLEIVLXVKUNS-BDAKNGLRSA-N 0.000 claims 1
- GCYULHICELESPR-MNOVXSKESA-N (1r,6s)-9-(5-methoxypyridin-3-yl)-4,9-diazabicyclo[4.2.1]nonane Chemical compound N1([C@@]2([H])CC[C@@]1(CCNC2)[H])C1=CN=CC(OC)=C1 GCYULHICELESPR-MNOVXSKESA-N 0.000 claims 1
- ASYILFSEFBVAHP-MNOVXSKESA-N (1r,6s)-9-(6-chloro-5-methylpyridin-3-yl)-4,9-diazabicyclo[4.2.1]nonane Chemical compound N1([C@@]2([H])CC[C@@]1(CCNC2)[H])C1=CN=C(Cl)C(C)=C1 ASYILFSEFBVAHP-MNOVXSKESA-N 0.000 claims 1
- IBCNMAGSFIKYFO-YUMQZZPRSA-N (1s,4s)-2-(5-bromo-6-chloropyridin-3-yl)-2,5-diazabicyclo[2.2.2]octane Chemical compound N1([C@@]2([H])CC[C@](NC2)(C1)[H])C1=CN=C(Cl)C(Br)=C1 IBCNMAGSFIKYFO-YUMQZZPRSA-N 0.000 claims 1
- XXQBILVDTXLLLR-UWVGGRQHSA-N (1s,4s)-2-(5-methoxypyridin-3-yl)-2,5-diazabicyclo[2.2.2]octane Chemical compound N1([C@@]2([H])CC[C@](NC2)(C1)[H])C1=CN=CC(OC)=C1 XXQBILVDTXLLLR-UWVGGRQHSA-N 0.000 claims 1
- XTBFEBHZTXDLNN-YUMQZZPRSA-N (1s,4s)-2-(6-chloro-5-methoxypyridin-3-yl)-2,5-diazabicyclo[2.2.1]heptane Chemical compound C([C@]1(NC[C@]2([H])C1)[H])N2C1=CN=C(Cl)C(OC)=C1 XTBFEBHZTXDLNN-YUMQZZPRSA-N 0.000 claims 1
- KDAZWLLKSUFNTG-UWVGGRQHSA-N (1s,4s)-2-(6-chloro-5-methylpyridin-3-yl)-2,5-diazabicyclo[2.2.2]octane Chemical compound N1([C@@]2([H])CC[C@](NC2)(C1)[H])C1=CN=C(Cl)C(C)=C1 KDAZWLLKSUFNTG-UWVGGRQHSA-N 0.000 claims 1
- IKJZJZXKGKENDY-ONGXEEELSA-N (1s,4s)-2-pyridin-3-yl-2,5-diazabicyclo[2.2.2]octane Chemical compound N1([C@@]2([H])CC[C@](NC2)(C1)[H])C1=CC=CN=C1 IKJZJZXKGKENDY-ONGXEEELSA-N 0.000 claims 1
- VSNFTKFKMDNYIB-VHSXEESVSA-N (1s,5r)-4-(5-methoxypyridin-3-yl)-4,7-diazabicyclo[3.2.1]octane Chemical compound N1([C@]2([H])C[C@@](NC2)(CC1)[H])C1=CN=CC(OC)=C1 VSNFTKFKMDNYIB-VHSXEESVSA-N 0.000 claims 1
- AFMGMCFRGXNXME-WCBMZHEXSA-N (1s,5r)-4-(6-fluoropyridin-3-yl)-4,7-diazabicyclo[3.2.1]octane Chemical compound N1([C@]2([H])C[C@@](NC2)(CC1)[H])C1=CC=C(F)N=C1 AFMGMCFRGXNXME-WCBMZHEXSA-N 0.000 claims 1
- WMYOQZRIEFMPDD-SFYZADRCSA-N (1s,5r)-7-(5-bromo-6-chloropyridin-3-yl)-4,7-diazabicyclo[3.2.1]octane Chemical compound C([C@]1(C[C@]2([H])CCN1)[H])N2C1=CN=C(Cl)C(Br)=C1 WMYOQZRIEFMPDD-SFYZADRCSA-N 0.000 claims 1
- MXMWDEJGOFAQIF-ZJUUUORDSA-N (1s,5r)-7-(5-methoxypyridin-3-yl)-4,7-diazabicyclo[3.2.1]octane Chemical compound C([C@]1(C[C@]2([H])CCN1)[H])N2C1=CN=CC(OC)=C1 MXMWDEJGOFAQIF-ZJUUUORDSA-N 0.000 claims 1
- LEJILTNCTMWMAF-MNOVXSKESA-N (1s,5r)-7-(6-chloro-5-ethynylpyridin-3-yl)-4,7-diazabicyclo[3.2.1]octane Chemical compound C([C@]1(C[C@]2([H])CCN1)[H])N2C1=CN=C(Cl)C(C#C)=C1 LEJILTNCTMWMAF-MNOVXSKESA-N 0.000 claims 1
- TVSYLDOEQMXDNJ-ZJUUUORDSA-N (1s,5r)-7-(6-chloro-5-methylpyridin-3-yl)-4,7-diazabicyclo[3.2.1]octane Chemical compound C([C@]1(C[C@]2([H])CCN1)[H])N2C1=CN=C(Cl)C(C)=C1 TVSYLDOEQMXDNJ-ZJUUUORDSA-N 0.000 claims 1
- DOLPRZLBJYAFEQ-ZJUUUORDSA-N (1s,5r)-7-(6-fluoro-5-methylpyridin-3-yl)-4,7-diazabicyclo[3.2.1]octane Chemical compound C([C@]1(C[C@]2([H])CCN1)[H])N2C1=CN=C(F)C(C)=C1 DOLPRZLBJYAFEQ-ZJUUUORDSA-N 0.000 claims 1
- LODFTIXAWYPTQJ-BDAKNGLRSA-N (1s,5r)-7-(6-fluoropyridin-3-yl)-4,7-diazabicyclo[3.2.1]octane Chemical compound C([C@]1(C[C@]2([H])CCN1)[H])N2C1=CC=C(F)N=C1 LODFTIXAWYPTQJ-BDAKNGLRSA-N 0.000 claims 1
- UYYPHVFFQXEJKF-YUMQZZPRSA-N (1s,5s)-3-(5-bromo-6-chloropyridin-3-yl)-3,6-diazabicyclo[3.2.1]octane Chemical compound C([C@@]1([H])NC[C@](C1)(C1)[H])N1C1=CN=C(Cl)C(Br)=C1 UYYPHVFFQXEJKF-YUMQZZPRSA-N 0.000 claims 1
- UVORMACRUDDZOI-UWVGGRQHSA-N (1s,5s)-3-(5-methoxypyridin-3-yl)-3,6-diazabicyclo[3.2.1]octane Chemical compound C([C@@]1([H])NC[C@](C1)(C1)[H])N1C1=CN=CC(OC)=C1 UVORMACRUDDZOI-UWVGGRQHSA-N 0.000 claims 1
- NSZNGOJYQHWDIQ-UWVGGRQHSA-N (1s,5s)-3-(6-chloro-5-methylpyridin-3-yl)-3,6-diazabicyclo[3.2.1]octane Chemical compound C([C@@]1([H])NC[C@](C1)(C1)[H])N1C1=CN=C(Cl)C(C)=C1 NSZNGOJYQHWDIQ-UWVGGRQHSA-N 0.000 claims 1
- HVFAVMAEHDLGFX-UWVGGRQHSA-N (1s,5s)-6-(5-methoxypyridin-3-yl)-3,6-diazabicyclo[3.2.1]octane Chemical compound C([C@]1(C[C@@]2([H])CNC1)[H])N2C1=CN=CC(OC)=C1 HVFAVMAEHDLGFX-UWVGGRQHSA-N 0.000 claims 1
- ZLFPSGCWGZRCNZ-ONGXEEELSA-N (1s,5s)-6-(6-chloro-5-ethynylpyridin-3-yl)-3,6-diazabicyclo[3.2.1]octane Chemical compound C([C@]1(C[C@@]2([H])CNC1)[H])N2C1=CN=C(Cl)C(C#C)=C1 ZLFPSGCWGZRCNZ-ONGXEEELSA-N 0.000 claims 1
- MOALZDBEPGDEKO-ONGXEEELSA-N (1s,5s)-6-(6-fluoro-5-methylpyridin-3-yl)-3,6-diazabicyclo[3.2.1]octane Chemical compound C([C@]1(C[C@@]2([H])CNC1)[H])N2C1=CN=C(F)C(C)=C1 MOALZDBEPGDEKO-ONGXEEELSA-N 0.000 claims 1
- RCUIVEFKYGBCPS-WPRPVWTQSA-N (1s,5s)-6-(6-fluoropyridin-3-yl)-3,6-diazabicyclo[3.2.1]octane Chemical compound C([C@]1(C[C@@]2([H])CNC1)[H])N2C1=CC=C(F)N=C1 RCUIVEFKYGBCPS-WPRPVWTQSA-N 0.000 claims 1
- ZLHFGGWPDZHAJF-ONGXEEELSA-N (1s,5s)-6-pyridin-3-yl-3,6-diazabicyclo[3.2.1]octane Chemical compound C([C@]1(C[C@@]2([H])CNC1)[H])N2C1=CC=CN=C1 ZLHFGGWPDZHAJF-ONGXEEELSA-N 0.000 claims 1
- GEWXCNBZLXRDAX-DTWKUNHWSA-N (1s,6r)-4-(5-bromo-6-chloropyridin-3-yl)-4,9-diazabicyclo[4.2.1]nonane Chemical compound C([C@]1(CC[C@@](CC2)(N1)[H])[H])N2C1=CN=C(Cl)C(Br)=C1 GEWXCNBZLXRDAX-DTWKUNHWSA-N 0.000 claims 1
- HEAXNRWRTMPNJF-NWDGAFQWSA-N (1s,6r)-4-(5-ethynyl-6-fluoropyridin-3-yl)-4,9-diazabicyclo[4.2.1]nonane Chemical compound C([C@]1(CC[C@@](CC2)(N1)[H])[H])N2C1=CN=C(F)C(C#C)=C1 HEAXNRWRTMPNJF-NWDGAFQWSA-N 0.000 claims 1
- XGLUSGAITGFVAL-WDEREUQCSA-N (1s,6r)-4-(5-methoxypyridin-3-yl)-4,9-diazabicyclo[4.2.1]nonane Chemical compound C([C@]1(CC[C@@](CC2)(N1)[H])[H])N2C1=CN=CC(OC)=C1 XGLUSGAITGFVAL-WDEREUQCSA-N 0.000 claims 1
- ZNBQVWOSKWWGGL-NWDGAFQWSA-N (1s,6r)-4-(6-chloro-5-ethynylpyridin-3-yl)-4,9-diazabicyclo[4.2.1]nonane Chemical compound C([C@]1(CC[C@@](CC2)(N1)[H])[H])N2C1=CN=C(Cl)C(C#C)=C1 ZNBQVWOSKWWGGL-NWDGAFQWSA-N 0.000 claims 1
- UBKMVKPQYKJIRD-WDEREUQCSA-N (1s,6r)-4-(6-chloro-5-methylpyridin-3-yl)-4,9-diazabicyclo[4.2.1]nonane Chemical compound C([C@]1(CC[C@@](CC2)(N1)[H])[H])N2C1=CN=C(Cl)C(C)=C1 UBKMVKPQYKJIRD-WDEREUQCSA-N 0.000 claims 1
- RWOLEIVLXVKUNS-DTWKUNHWSA-N (1s,6r)-9-(5,6-dichloropyridin-3-yl)-4,9-diazabicyclo[4.2.1]nonane Chemical compound N1([C@]2([H])CC[C@]1(CCNC2)[H])C1=CN=C(Cl)C(Cl)=C1 RWOLEIVLXVKUNS-DTWKUNHWSA-N 0.000 claims 1
- ASYILFSEFBVAHP-WDEREUQCSA-N (1s,6r)-9-(6-chloro-5-methylpyridin-3-yl)-4,9-diazabicyclo[4.2.1]nonane Chemical compound N1([C@]2([H])CC[C@]1(CCNC2)[H])C1=CN=C(Cl)C(C)=C1 ASYILFSEFBVAHP-WDEREUQCSA-N 0.000 claims 1
- UHVDNONGKVDHEZ-CMPLNLGQSA-N (1s,6r)-9-pyridin-3-yl-4,9-diazabicyclo[4.2.1]nonane Chemical compound N1([C@]2([H])CC[C@]1(CCNC2)[H])C1=CC=CN=C1 UHVDNONGKVDHEZ-CMPLNLGQSA-N 0.000 claims 1
- BYYIXAPRYVEOEB-RKDXNWHRSA-N 1-chloro-4-[(1r,4r)-2,5-diazabicyclo[2.2.1]heptan-2-yl]phthalazine Chemical compound C1=CC=C2C(N3C[C@@]4(NC[C@@]3([H])C4)[H])=NN=C(Cl)C2=C1 BYYIXAPRYVEOEB-RKDXNWHRSA-N 0.000 claims 1
- BYYIXAPRYVEOEB-IUCAKERBSA-N 1-chloro-4-[(1s,4s)-2,5-diazabicyclo[2.2.1]heptan-2-yl]phthalazine Chemical compound C1=CC=C2C(N3C[C@]4(NC[C@]3([H])C4)[H])=NN=C(Cl)C2=C1 BYYIXAPRYVEOEB-IUCAKERBSA-N 0.000 claims 1
- FRVGBUBUZLXEJI-UHFFFAOYSA-N 2-(6-chloro-5-methylpyridin-3-yl)-2,5-diazabicyclo[2.2.1]heptane Chemical compound N1=C(Cl)C(C)=CC(N2C3CC(NC3)C2)=C1 FRVGBUBUZLXEJI-UHFFFAOYSA-N 0.000 claims 1
- ONPXTLLWQNBLPG-UHFFFAOYSA-N 2-(6-fluoropyridin-3-yl)-2,5-diazabicyclo[2.2.1]heptane Chemical compound C1=NC(F)=CC=C1N1C(CN2)CC2C1 ONPXTLLWQNBLPG-UHFFFAOYSA-N 0.000 claims 1
- HNRIHCBMMRMJDG-UHFFFAOYSA-N 2-(6-methoxypyridin-3-yl)-2,5-diazabicyclo[2.2.1]heptane Chemical compound C1=NC(OC)=CC=C1N1C(CN2)CC2C1 HNRIHCBMMRMJDG-UHFFFAOYSA-N 0.000 claims 1
- MDWOWXOFKFFTAB-UHFFFAOYSA-N 2-(6-methylpyridin-3-yl)-2,5-diazabicyclo[2.2.1]heptane Chemical compound C1=NC(C)=CC=C1N1C(CN2)CC2C1 MDWOWXOFKFFTAB-UHFFFAOYSA-N 0.000 claims 1
- LVEDPTDGTCVLOE-UHFFFAOYSA-N 2-chloro-5-(3,7-diazabicyclo[3.3.1]nonan-3-yl)pyridine-3-carbonitrile Chemical compound C1=C(C#N)C(Cl)=NC=C1N1CC(C2)CNCC2C1 LVEDPTDGTCVLOE-UHFFFAOYSA-N 0.000 claims 1
- QTGGWVSXJFOQQA-UHFFFAOYSA-N 2-chloro-5-(3,8-diazabicyclo[3.2.1]octan-3-yl)pyridine-3-carbonitrile Chemical compound C1=C(C#N)C(Cl)=NC=C1N1CC(N2)CCC2C1 QTGGWVSXJFOQQA-UHFFFAOYSA-N 0.000 claims 1
- NRFYACWYEJZMRE-PSASIEDQSA-N 2-chloro-5-[(1r,4r)-2,5-diazabicyclo[2.2.1]heptan-2-yl]pyridine-3-carbonitrile Chemical compound C([C@@]1(NC[C@@]2([H])C1)[H])N2C1=CN=C(Cl)C(C#N)=C1 NRFYACWYEJZMRE-PSASIEDQSA-N 0.000 claims 1
- YWXHDGVOLPDNSV-NXEZZACHSA-N 2-chloro-5-[(1r,4r)-2,5-diazabicyclo[2.2.2]octan-2-yl]pyridine-3-carbonitrile Chemical compound N1([C@]2([H])CC[C@@](NC2)(C1)[H])C1=CN=C(Cl)C(C#N)=C1 YWXHDGVOLPDNSV-NXEZZACHSA-N 0.000 claims 1
- ORTIGJSCTJQDMP-PSASIEDQSA-N 2-chloro-5-[(1r,5r)-3,6-diazabicyclo[3.2.1]octan-6-yl]pyridine-3-carbonitrile Chemical compound C([C@@]1(C[C@]2([H])CNC1)[H])N2C1=CN=C(Cl)C(C#N)=C1 ORTIGJSCTJQDMP-PSASIEDQSA-N 0.000 claims 1
- FEVLGLCNQGLREU-KOLCDFICSA-N 2-chloro-5-[(1r,5s)-4,7-diazabicyclo[3.2.1]octan-4-yl]pyridine-3-carbonitrile Chemical compound N1([C@@]2([H])C[C@](NC2)(CC1)[H])C1=CN=C(Cl)C(C#N)=C1 FEVLGLCNQGLREU-KOLCDFICSA-N 0.000 claims 1
- CUVZIAWUWKJYRZ-VHSXEESVSA-N 2-chloro-5-[(1r,5s)-4,7-diazabicyclo[3.2.1]octan-7-yl]pyridine-3-carbonitrile Chemical compound C([C@@]1(C[C@@]2([H])CCN1)[H])N2C1=CN=C(Cl)C(C#N)=C1 CUVZIAWUWKJYRZ-VHSXEESVSA-N 0.000 claims 1
- FEVLGLCNQGLREU-GXSJLCMTSA-N 2-chloro-5-[(1s,5r)-4,7-diazabicyclo[3.2.1]octan-4-yl]pyridine-3-carbonitrile Chemical compound N1([C@]2([H])C[C@@](NC2)(CC1)[H])C1=CN=C(Cl)C(C#N)=C1 FEVLGLCNQGLREU-GXSJLCMTSA-N 0.000 claims 1
- FBYJNKLXXDUKPJ-WPRPVWTQSA-N 2-chloro-5-[(1s,5s)-3,6-diazabicyclo[3.2.1]octan-3-yl]pyridine-3-carbonitrile Chemical compound C([C@@]1([H])NC[C@](C1)(C1)[H])N1C1=CN=C(Cl)C(C#N)=C1 FBYJNKLXXDUKPJ-WPRPVWTQSA-N 0.000 claims 1
- GTFIBWYZLKFYGQ-UHFFFAOYSA-N 3-(5,6-dichloropyridin-3-yl)-3,8-diazabicyclo[3.2.1]octane Chemical compound N1=C(Cl)C(Cl)=CC(N2CC3CCC(N3)C2)=C1 GTFIBWYZLKFYGQ-UHFFFAOYSA-N 0.000 claims 1
- XSENXYRHJRRCCP-UHFFFAOYSA-N 3-(5-bromo-6-chloropyridin-3-yl)-3,7-diazabicyclo[3.3.1]nonane Chemical compound C1=C(Br)C(Cl)=NC=C1N1CC(C2)CNCC2C1 XSENXYRHJRRCCP-UHFFFAOYSA-N 0.000 claims 1
- XKHAMSWZBIFYEF-UHFFFAOYSA-N 3-(5-bromo-6-chloropyridin-3-yl)-3,8-diazabicyclo[3.2.1]octane Chemical compound C1=C(Br)C(Cl)=NC=C1N1CC(N2)CCC2C1 XKHAMSWZBIFYEF-UHFFFAOYSA-N 0.000 claims 1
- KKXRWJXNPLBROS-UHFFFAOYSA-N 3-(5-ethynyl-6-fluoropyridin-3-yl)-3,7-diazabicyclo[3.3.1]nonane Chemical compound C1=C(C#C)C(F)=NC=C1N1CC(C2)CNCC2C1 KKXRWJXNPLBROS-UHFFFAOYSA-N 0.000 claims 1
- AYECEKGNILHLRL-UHFFFAOYSA-N 3-(5-ethynyl-6-fluoropyridin-3-yl)-3,8-diazabicyclo[3.2.1]octane Chemical compound C1=C(C#C)C(F)=NC=C1N1CC(N2)CCC2C1 AYECEKGNILHLRL-UHFFFAOYSA-N 0.000 claims 1
- BNPCEETXPUKHLC-UHFFFAOYSA-N 3-(6-chloro-5-ethynylpyridin-3-yl)-3,7-diazabicyclo[3.3.1]nonane Chemical compound C1=C(C#C)C(Cl)=NC=C1N1CC(C2)CNCC2C1 BNPCEETXPUKHLC-UHFFFAOYSA-N 0.000 claims 1
- TXSUUUHHYAMRKK-UHFFFAOYSA-N 3-(6-chloro-5-ethynylpyridin-3-yl)-3,8-diazabicyclo[3.2.1]octane Chemical compound C1=C(C#C)C(Cl)=NC=C1N1CC(N2)CCC2C1 TXSUUUHHYAMRKK-UHFFFAOYSA-N 0.000 claims 1
- BXQVWZDNOZKPLA-UHFFFAOYSA-N 3-(6-chloropyridin-3-yl)-3,8-diazabicyclo[3.2.1]octane Chemical compound C1=NC(Cl)=CC=C1N1CC(N2)CCC2C1 BXQVWZDNOZKPLA-UHFFFAOYSA-N 0.000 claims 1
- RPBHQOWASYRAGS-UHFFFAOYSA-N 3-(6-fluoro-5-methylpyridin-3-yl)-3,7-diazabicyclo[3.3.1]nonane Chemical compound N1=C(F)C(C)=CC(N2CC3CNCC(C3)C2)=C1 RPBHQOWASYRAGS-UHFFFAOYSA-N 0.000 claims 1
- CVLNMKCUYYJTQN-UHFFFAOYSA-N 3-(6-fluoro-5-methylpyridin-3-yl)-3,8-diazabicyclo[3.2.1]octane Chemical compound N1=C(F)C(C)=CC(N2CC3CCC(N3)C2)=C1 CVLNMKCUYYJTQN-UHFFFAOYSA-N 0.000 claims 1
- BLYYOMPZEPOXIT-UHFFFAOYSA-N 3-(6-fluoropyridin-3-yl)-3,8-diazabicyclo[3.2.1]octane Chemical compound C1=NC(F)=CC=C1N1CC(N2)CCC2C1 BLYYOMPZEPOXIT-UHFFFAOYSA-N 0.000 claims 1
- KVCPNCMGNJWKCS-UHFFFAOYSA-N 3-(6-nitropyridin-3-yl)-3,8-diazabicyclo[3.2.1]octane Chemical compound C1=NC([N+](=O)[O-])=CC=C1N1CC(N2)CCC2C1 KVCPNCMGNJWKCS-UHFFFAOYSA-N 0.000 claims 1
- VMNQBOWUPKNWAS-DGCLKSJQSA-N 3-[(1r,4r)-2,5-diazabicyclo[2.2.1]heptan-2-yl]quinoline Chemical compound C1=CC=CC2=CC(N3C[C@@]4(NC[C@@]3([H])C4)[H])=CN=C21 VMNQBOWUPKNWAS-DGCLKSJQSA-N 0.000 claims 1
- QGPJNUIJAGMDMT-UHFFFAOYSA-N 3-pyridin-3-yl-3,7-diazabicyclo[3.3.1]nonane Chemical compound C1NCC(C2)CC1CN2C1=CC=CN=C1 QGPJNUIJAGMDMT-UHFFFAOYSA-N 0.000 claims 1
- GFPKENYJHPZLJI-UHFFFAOYSA-N 3-pyridin-3-yl-3,8-diazabicyclo[3.2.1]octane Chemical compound C1C(N2)CCC2CN1C1=CC=CN=C1 GFPKENYJHPZLJI-UHFFFAOYSA-N 0.000 claims 1
- JYFFKBVSSSXOBJ-UHFFFAOYSA-N 4-(6-chloropyridin-3-yl)-4,7-diazabicyclo[3.2.1]octane Chemical compound C1=NC(Cl)=CC=C1N1C(CN2)CC2CC1 JYFFKBVSSSXOBJ-UHFFFAOYSA-N 0.000 claims 1
- RXMPTHLJGKSEAG-UHFFFAOYSA-N 4-pyridin-3-yl-4,7-diazabicyclo[3.2.1]octane Chemical compound C1NC(CC2)CC1N2C1=CC=CN=C1 RXMPTHLJGKSEAG-UHFFFAOYSA-N 0.000 claims 1
- IMAFPMMJFGWHQM-UHFFFAOYSA-N 4-pyridin-3-yl-4,9-diazabicyclo[4.2.1]nonane Chemical compound C1CC(N2)CCC2CN1C1=CC=CN=C1 IMAFPMMJFGWHQM-UHFFFAOYSA-N 0.000 claims 1
- CJRLDFQDWXLGLH-UHFFFAOYSA-N 5-(2,5-diazabicyclo[2.2.1]heptan-2-yl)pyridine-3-carbonitrile Chemical compound N#CC1=CN=CC(N2C3CC(NC3)C2)=C1 CJRLDFQDWXLGLH-UHFFFAOYSA-N 0.000 claims 1
- IYNBYHMSSSABOB-UHFFFAOYSA-N 5-(2,5-diazabicyclo[2.2.1]heptan-2-yl)pyridine-3-carboxamide Chemical compound NC(=O)C1=CN=CC(N2C3CC(NC3)C2)=C1 IYNBYHMSSSABOB-UHFFFAOYSA-N 0.000 claims 1
- ZHJMFUVNZRJUNC-UHFFFAOYSA-N 5-(3,7-diazabicyclo[3.3.1]nonan-3-yl)-2-fluoropyridine-3-carbonitrile Chemical compound C1=C(C#N)C(F)=NC=C1N1CC(C2)CNCC2C1 ZHJMFUVNZRJUNC-UHFFFAOYSA-N 0.000 claims 1
- XIEKCSAAGQQQEN-UHFFFAOYSA-N 5-(3,8-diazabicyclo[3.2.1]octan-3-yl)-2-fluoropyridine-3-carbonitrile Chemical compound C1=C(C#N)C(F)=NC=C1N1CC(N2)CCC2C1 XIEKCSAAGQQQEN-UHFFFAOYSA-N 0.000 claims 1
- PZYQHIBWPHJONC-RNFRBKRXSA-N 5-[(1r,4r)-2,5-diazabicyclo[2.2.1]heptan-2-yl]-2-fluoropyridine-3-carboxamide Chemical compound C([C@@]1(NC[C@@]2([H])C1)[H])N2C1=CN=C(F)C(C(N)=O)=C1 PZYQHIBWPHJONC-RNFRBKRXSA-N 0.000 claims 1
- DKGVDEQTBDIKJT-RNFRBKRXSA-N 5-[(1r,4r)-2,5-diazabicyclo[2.2.1]heptan-2-yl]-2-fluoropyridine-3-sulfonamide Chemical compound C([C@@]1(NC[C@@]2([H])C1)[H])N2C1=CN=C(F)C(S(N)(=O)=O)=C1 DKGVDEQTBDIKJT-RNFRBKRXSA-N 0.000 claims 1
- QASONRSLKVKRRW-VXNVDRBHSA-N 5-[(1r,4r)-2,5-diazabicyclo[2.2.1]heptan-2-yl]pyridin-2-amine Chemical compound C([C@@]1(NC[C@@]2([H])C1)[H])N2C1=CC=C(N)N=C1 QASONRSLKVKRRW-VXNVDRBHSA-N 0.000 claims 1
- NMHTXPVGXBELTF-PSASIEDQSA-N 5-[(1r,4r)-2,5-diazabicyclo[2.2.1]heptan-2-yl]pyridine-3-carboxylic acid Chemical compound C([C@@]1(NC[C@@]2([H])C1)[H])N2C1=CN=CC(C(O)=O)=C1 NMHTXPVGXBELTF-PSASIEDQSA-N 0.000 claims 1
- BECWZRXACRFJSJ-NXEZZACHSA-N 5-[(1r,4r)-2,5-diazabicyclo[2.2.2]octan-2-yl]-2-fluoropyridine-3-carbonitrile Chemical compound N1([C@]2([H])CC[C@@](NC2)(C1)[H])C1=CN=C(F)C(C#N)=C1 BECWZRXACRFJSJ-NXEZZACHSA-N 0.000 claims 1
- LQLAUJRHAMOUED-PSASIEDQSA-N 5-[(1r,5r)-3,6-diazabicyclo[3.2.1]octan-3-yl]-2-fluoropyridine-3-carbonitrile Chemical compound C([C@]1([H])NC[C@@](C1)(C1)[H])N1C1=CN=C(F)C(C#N)=C1 LQLAUJRHAMOUED-PSASIEDQSA-N 0.000 claims 1
- XGJDNJRTCFICRH-KOLCDFICSA-N 5-[(1r,5s)-4,7-diazabicyclo[3.2.1]octan-4-yl]-2-fluoropyridine-3-carbonitrile Chemical compound N1([C@@]2([H])C[C@](NC2)(CC1)[H])C1=CN=C(F)C(C#N)=C1 XGJDNJRTCFICRH-KOLCDFICSA-N 0.000 claims 1
- UQIHEDIZDFLMGR-MNOVXSKESA-N 5-[(1r,6s)-4,9-diazabicyclo[4.2.1]nonan-4-yl]-2-fluoropyridine-3-carbonitrile Chemical compound C([C@@]1(CC[C@](CC2)(N1)[H])[H])N2C1=CN=C(F)C(C#N)=C1 UQIHEDIZDFLMGR-MNOVXSKESA-N 0.000 claims 1
- BECWZRXACRFJSJ-UWVGGRQHSA-N 5-[(1s,4s)-2,5-diazabicyclo[2.2.2]octan-2-yl]-2-fluoropyridine-3-carbonitrile Chemical compound N1([C@@]2([H])CC[C@](NC2)(C1)[H])C1=CN=C(F)C(C#N)=C1 BECWZRXACRFJSJ-UWVGGRQHSA-N 0.000 claims 1
- XGJDNJRTCFICRH-GXSJLCMTSA-N 5-[(1s,5r)-4,7-diazabicyclo[3.2.1]octan-4-yl]-2-fluoropyridine-3-carbonitrile Chemical compound N1([C@]2([H])C[C@@](NC2)(CC1)[H])C1=CN=C(F)C(C#N)=C1 XGJDNJRTCFICRH-GXSJLCMTSA-N 0.000 claims 1
- WPZMIBQCEGHJIJ-ZJUUUORDSA-N 5-[(1s,5r)-4,7-diazabicyclo[3.2.1]octan-7-yl]-2-fluoropyridine-3-carbonitrile Chemical compound C([C@]1(C[C@]2([H])CCN1)[H])N2C1=CN=C(F)C(C#N)=C1 WPZMIBQCEGHJIJ-ZJUUUORDSA-N 0.000 claims 1
- DKWMODXHMFPHAL-WPRPVWTQSA-N 5-[(1s,5s)-3,6-diazabicyclo[3.2.1]octan-6-yl]-2-fluoropyridine-3-carbonitrile Chemical compound C([C@]1(C[C@@]2([H])CNC1)[H])N2C1=CN=C(F)C(C#N)=C1 DKWMODXHMFPHAL-WPRPVWTQSA-N 0.000 claims 1
- UQIHEDIZDFLMGR-WDEREUQCSA-N 5-[(1s,6r)-4,9-diazabicyclo[4.2.1]nonan-4-yl]-2-fluoropyridine-3-carbonitrile Chemical compound C([C@]1(CC[C@@](CC2)(N1)[H])[H])N2C1=CN=C(F)C(C#N)=C1 UQIHEDIZDFLMGR-WDEREUQCSA-N 0.000 claims 1
- RRRYINNWGCSIAD-UHFFFAOYSA-N 9-(6-chloropyridin-3-yl)-4,9-diazabicyclo[4.2.1]nonane Chemical compound C1=NC(Cl)=CC=C1N1C2CCC1CCNC2 RRRYINNWGCSIAD-UHFFFAOYSA-N 0.000 claims 1
- GHUUBYQTCDQWRA-UHFFFAOYSA-N Pioglitazone hydrochloride Chemical compound Cl.N1=CC(CC)=CC=C1CCOC(C=C1)=CC=C1CC1C(=O)NC(=O)S1 GHUUBYQTCDQWRA-UHFFFAOYSA-N 0.000 claims 1
- WDOZGCODRNWIDT-UHFFFAOYSA-N [2-chloro-5-(3,8-diazabicyclo[3.2.1]octan-3-yl)pyridin-3-yl]methanamine Chemical compound N1=C(Cl)C(CN)=CC(N2CC3CCC(N3)C2)=C1 WDOZGCODRNWIDT-UHFFFAOYSA-N 0.000 claims 1
- QFIWARNELUAESQ-PSASIEDQSA-N [2-chloro-5-[(1r,4r)-2,5-diazabicyclo[2.2.1]heptan-2-yl]pyridin-3-yl]methanol Chemical compound C([C@@]1(NC[C@@]2([H])C1)[H])N2C1=CN=C(Cl)C(CO)=C1 QFIWARNELUAESQ-PSASIEDQSA-N 0.000 claims 1
- NPAKPPPNWNHVFU-UHFFFAOYSA-N [5-(3,8-diazabicyclo[3.2.1]octan-3-yl)pyridin-3-yl]methanamine Chemical compound NCC1=CN=CC(N2CC3CCC(N3)C2)=C1 NPAKPPPNWNHVFU-UHFFFAOYSA-N 0.000 claims 1
- HBQXFEJDQXXDQI-PSASIEDQSA-N [5-[(1r,4r)-2,5-diazabicyclo[2.2.1]heptan-2-yl]-2-fluoropyridin-3-yl]methanamine Chemical compound C([C@@]1(NC[C@@]2([H])C1)[H])N2C1=CN=C(F)C(CN)=C1 HBQXFEJDQXXDQI-PSASIEDQSA-N 0.000 claims 1
- XVNHHYYONOJITJ-MWLCHTKSSA-N [5-[(1r,4r)-2,5-diazabicyclo[2.2.1]heptan-2-yl]pyridin-3-yl]methanamine Chemical compound C([C@@]1(NC[C@@]2([H])C1)[H])N2C1=CN=CC(CN)=C1 XVNHHYYONOJITJ-MWLCHTKSSA-N 0.000 claims 1
- NEGLYMARULVTCX-WPRPVWTQSA-N [5-[(1s,4s)-2,5-diazabicyclo[2.2.1]heptan-2-yl]-2-fluoropyridin-3-yl]methanol Chemical compound C([C@]1(NC[C@]2([H])C1)[H])N2C1=CN=C(F)C(CO)=C1 NEGLYMARULVTCX-WPRPVWTQSA-N 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- KWKAKUADMBZCLK-UHFFFAOYSA-N methyl heptene Natural products CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 claims 1
- JWHHCJGBKVTLRR-PSASIEDQSA-N n-[[2-chloro-5-[(1r,4r)-2,5-diazabicyclo[2.2.1]heptan-2-yl]pyridin-3-yl]methylidene]hydroxylamine Chemical compound C([C@@]1(NC[C@@]2([H])C1)[H])N2C1=CN=C(Cl)C(C=NO)=C1 JWHHCJGBKVTLRR-PSASIEDQSA-N 0.000 claims 1
- JWHHCJGBKVTLRR-WPRPVWTQSA-N n-[[2-chloro-5-[(1s,4s)-2,5-diazabicyclo[2.2.1]heptan-2-yl]pyridin-3-yl]methylidene]hydroxylamine Chemical compound C([C@]1(NC[C@]2([H])C1)[H])N2C1=CN=C(Cl)C(C=NO)=C1 JWHHCJGBKVTLRR-WPRPVWTQSA-N 0.000 claims 1
- LVWUHTYFVOCQPY-WPRPVWTQSA-N n-[[5-[(1s,4s)-2,5-diazabicyclo[2.2.1]heptan-2-yl]-2-fluoropyridin-3-yl]methylidene]hydroxylamine Chemical compound C([C@]1(NC[C@]2([H])C1)[H])N2C1=CN=C(F)C(C=NO)=C1 LVWUHTYFVOCQPY-WPRPVWTQSA-N 0.000 claims 1
- 239000002858 neurotransmitter agent Substances 0.000 description 15
- 230000001242 postsynaptic effect Effects 0.000 description 11
- 210000004379 membrane Anatomy 0.000 description 10
- 239000012528 membrane Substances 0.000 description 10
- 230000005062 synaptic transmission Effects 0.000 description 10
- 210000004027 cell Anatomy 0.000 description 9
- 229940079593 drug Drugs 0.000 description 8
- 210000003169 central nervous system Anatomy 0.000 description 7
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 6
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 6
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 6
- 229960002715 nicotine Drugs 0.000 description 6
- 102000005962 receptors Human genes 0.000 description 6
- 108020003175 receptors Proteins 0.000 description 6
- 206010001497 Agitation Diseases 0.000 description 5
- 230000009471 action Effects 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 230000003518 presynaptic effect Effects 0.000 description 5
- 102000014415 Muscarinic acetylcholine receptor Human genes 0.000 description 4
- 108050003473 Muscarinic acetylcholine receptor Proteins 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 210000005036 nerve Anatomy 0.000 description 4
- 108091006146 Channels Proteins 0.000 description 3
- 102000009660 Cholinergic Receptors Human genes 0.000 description 3
- 108010009685 Cholinergic Receptors Proteins 0.000 description 3
- 230000004913 activation Effects 0.000 description 3
- 230000005540 biological transmission Effects 0.000 description 3
- 230000001713 cholinergic effect Effects 0.000 description 3
- 229960003638 dopamine Drugs 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 230000035699 permeability Effects 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- YLPCXVWMHNNQGI-UHFFFAOYSA-N 1,2-diazabicyclo[3.2.1]octane Chemical class C1C2CCN1NCC2 YLPCXVWMHNNQGI-UHFFFAOYSA-N 0.000 description 2
- 101100477360 Arabidopsis thaliana IPSP gene Proteins 0.000 description 2
- 102000004659 Presynaptic Receptors Human genes 0.000 description 2
- 108010003717 Presynaptic Receptors Proteins 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical class C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 2
- 229960004373 acetylcholine Drugs 0.000 description 2
- 230000036982 action potential Effects 0.000 description 2
- HJJPJSXJAXAIPN-UHFFFAOYSA-N arecoline Chemical compound COC(=O)C1=CCCN(C)C1 HJJPJSXJAXAIPN-UHFFFAOYSA-N 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 230000004907 flux Effects 0.000 description 2
- 210000002064 heart cell Anatomy 0.000 description 2
- 208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 description 2
- 230000001404 mediated effect Effects 0.000 description 2
- 230000001537 neural effect Effects 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical class [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 210000003463 organelle Anatomy 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 210000002027 skeletal muscle Anatomy 0.000 description 2
- 230000000946 synaptic effect Effects 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- GXFZCDMWGMFGFL-KKXMJGKMSA-N (+)-Tubocurarine chloride hydrochloride Chemical compound [Cl-].[Cl-].C([C@H]1[N+](C)(C)CCC=2C=C(C(=C(OC3=CC=C(C=C3)C[C@H]3C=4C=C(C(=CC=4CC[NH+]3C)OC)O3)C=21)O)OC)C1=CC=C(O)C3=C1 GXFZCDMWGMFGFL-KKXMJGKMSA-N 0.000 description 1
- QUTYKIXIUDQOLK-PRJMDXOYSA-N 5-O-(1-carboxyvinyl)-3-phosphoshikimic acid Chemical compound O[C@H]1[C@H](OC(=C)C(O)=O)CC(C(O)=O)=C[C@H]1OP(O)(O)=O QUTYKIXIUDQOLK-PRJMDXOYSA-N 0.000 description 1
- AFWQPVUHNZFYNY-UHFFFAOYSA-N 8-(6-chloropyrazin-2-yl)-3,8-diazabicyclo[3.2.1]octane Chemical compound ClC1=CN=CC(N2C3CCC2CNC3)=N1 AFWQPVUHNZFYNY-UHFFFAOYSA-N 0.000 description 1
- 208000007848 Alcoholism Diseases 0.000 description 1
- 206010002660 Anoxia Diseases 0.000 description 1
- 241000976983 Anoxia Species 0.000 description 1
- 101000768857 Arabidopsis thaliana 3-phosphoshikimate 1-carboxyvinyltransferase, chloroplastic Proteins 0.000 description 1
- 102000007527 Autoreceptors Human genes 0.000 description 1
- 108010071131 Autoreceptors Proteins 0.000 description 1
- 241001111317 Chondrodendron tomentosum Species 0.000 description 1
- 239000008709 Curare Substances 0.000 description 1
- 208000020401 Depressive disease Diseases 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 108091006027 G proteins Proteins 0.000 description 1
- 102000030782 GTP binding Human genes 0.000 description 1
- 108091000058 GTP-Binding Proteins 0.000 description 1
- SQUHHTBVTRBESD-UHFFFAOYSA-N Hexa-Ac-myo-Inositol Natural products CC(=O)OC1C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C1OC(C)=O SQUHHTBVTRBESD-UHFFFAOYSA-N 0.000 description 1
- 206010021143 Hypoxia Diseases 0.000 description 1
- KOTOUBGHZHWCCJ-UHFFFAOYSA-N IPSP Chemical compound CCS(=O)CSP(=S)(OC(C)C)OC(C)C KOTOUBGHZHWCCJ-UHFFFAOYSA-N 0.000 description 1
- 108090000862 Ion Channels Proteins 0.000 description 1
- 102000004310 Ion Channels Human genes 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 206010027646 Miosis Diseases 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 208000027089 Parkinsonian disease Diseases 0.000 description 1
- 206010034010 Parkinsonism Diseases 0.000 description 1
- 208000001871 Tachycardia Diseases 0.000 description 1
- 206010044565 Tremor Diseases 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000000556 agonist Substances 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 229940035676 analgesics Drugs 0.000 description 1
- 230000007953 anoxia Effects 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 230000002253 anti-ischaemic effect Effects 0.000 description 1
- 230000003502 anti-nociceptive effect Effects 0.000 description 1
- 239000003416 antiarrhythmic agent Substances 0.000 description 1
- 230000002567 autonomic effect Effects 0.000 description 1
- 210000003050 axon Anatomy 0.000 description 1
- 208000022362 bacterial infectious disease Diseases 0.000 description 1
- 230000006399 behavior Effects 0.000 description 1
- 230000003542 behavioural effect Effects 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- AIXAANGOTKPUOY-UHFFFAOYSA-N carbachol Chemical compound [Cl-].C[N+](C)(C)CCOC(N)=O AIXAANGOTKPUOY-UHFFFAOYSA-N 0.000 description 1
- 229960004484 carbachol Drugs 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 208000015114 central nervous system disease Diseases 0.000 description 1
- 239000000064 cholinergic agonist Substances 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 230000001086 cytosolic effect Effects 0.000 description 1
- 230000013872 defecation Effects 0.000 description 1
- 230000002999 depolarising effect Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 230000004064 dysfunction Effects 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 230000002964 excitative effect Effects 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- 208000024386 fungal infectious disease Diseases 0.000 description 1
- 210000001156 gastric mucosa Anatomy 0.000 description 1
- 210000005003 heart tissue Anatomy 0.000 description 1
- 230000011132 hemopoiesis Effects 0.000 description 1
- 150000002390 heteroarenes Chemical class 0.000 description 1
- 230000002102 hyperpolarization Effects 0.000 description 1
- 230000002631 hypothermal effect Effects 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000036734 inhibitory postsynaptic potential Effects 0.000 description 1
- 229960000367 inositol Drugs 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- 230000028161 membrane depolarization Effects 0.000 description 1
- 210000001259 mesencephalon Anatomy 0.000 description 1
- 230000003278 mimic effect Effects 0.000 description 1
- 230000003547 miosis Effects 0.000 description 1
- 210000000653 nervous system Anatomy 0.000 description 1
- 239000000842 neuromuscular blocking agent Substances 0.000 description 1
- 210000002569 neuron Anatomy 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 210000001428 peripheral nervous system Anatomy 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 150000003216 pyrazines Chemical class 0.000 description 1
- CDAISMWEOUEBRE-UHFFFAOYSA-N scyllo-inosotol Natural products OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 description 1
- 230000003248 secreting effect Effects 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 229940125723 sedative agent Drugs 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 230000000391 smoking effect Effects 0.000 description 1
- 210000000329 smooth muscle myocyte Anatomy 0.000 description 1
- 230000000392 somatic effect Effects 0.000 description 1
- 210000000278 spinal cord Anatomy 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- AXOIZCJOOAYSMI-UHFFFAOYSA-N succinylcholine Chemical compound C[N+](C)(C)CCOC(=O)CCC(=O)OCC[N+](C)(C)C AXOIZCJOOAYSMI-UHFFFAOYSA-N 0.000 description 1
- 229940032712 succinylcholine Drugs 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 210000000225 synapse Anatomy 0.000 description 1
- 210000002182 synaptic membrane Anatomy 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 230000006794 tachycardia Effects 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- 150000003557 thiazoles Chemical class 0.000 description 1
- 229930192474 thiophene Chemical class 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/08—Bridged systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/08—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing alicyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/10—Drugs for genital or sexual disorders; Contraceptives for impotence
-
- 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
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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
- A61P25/06—Antimigraine agents
-
- 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
- A61P25/08—Antiepileptics; Anticonvulsants
-
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- 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
- A61P25/20—Hypnotics; Sedatives
-
- 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
- A61P25/22—Anxiolytics
-
- 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
- A61P25/24—Antidepressants
-
- 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
- A61P25/34—Tobacco-abuse
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/08—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing alicyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/08—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing alicyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/08—Bridged systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Addiction (AREA)
- Endocrinology (AREA)
- Urology & Nephrology (AREA)
- Reproductive Health (AREA)
- Vascular Medicine (AREA)
- Hospice & Palliative Care (AREA)
- Anesthesiology (AREA)
- Rheumatology (AREA)
- Gynecology & Obstetrics (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US23983899A | 1999-01-29 | 1999-01-29 |
Publications (1)
Publication Number | Publication Date |
---|---|
ZA200105835B true ZA200105835B (en) | 2002-10-16 |
Family
ID=22903947
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ZA200105835A ZA200105835B (en) | 1999-01-29 | 2001-07-16 | Diazabicyclic derivatives as nicotinic acetylcholine receptor ligands. |
Country Status (26)
Country | Link |
---|---|
EP (2) | EP1359152B1 (es) |
JP (1) | JP4676062B2 (es) |
KR (1) | KR20010101725A (es) |
CN (2) | CN1636996A (es) |
AR (1) | AR034538A1 (es) |
AT (2) | ATE394401T1 (es) |
AU (1) | AU773795B2 (es) |
BG (1) | BG105836A (es) |
BR (1) | BR0007664A (es) |
CA (1) | CA2361525C (es) |
CO (1) | CO5150231A1 (es) |
CZ (1) | CZ20012716A3 (es) |
DE (2) | DE60006213T2 (es) |
DK (1) | DK1147112T3 (es) |
ES (2) | ES2305373T3 (es) |
HK (1) | HK1043116B (es) |
HU (1) | HUP0200332A3 (es) |
IL (1) | IL144340A0 (es) |
NO (1) | NO20013731L (es) |
NZ (1) | NZ512884A (es) |
PT (1) | PT1147112E (es) |
SK (1) | SK10692001A3 (es) |
TR (1) | TR200102162T2 (es) |
TW (1) | TW200300021A (es) |
WO (1) | WO2000044755A1 (es) |
ZA (1) | ZA200105835B (es) |
Families Citing this family (78)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6605610B1 (en) * | 1997-12-31 | 2003-08-12 | Pfizer Inc | Aryl fused azapolycyclic compounds |
NZ504482A (en) | 1997-12-31 | 2003-01-31 | Pfizer Prod Inc | Aryl fused azapolycyclic compounds and pharmaceuticals thereof which bind to neuronal nicotinic acetylcholine specific recpetor sites and are useful for modulating cholinergic function |
US6815438B2 (en) | 1999-12-14 | 2004-11-09 | Neurosearch A/S | Heteroaryl-diazabicycloalkanes |
MY137020A (en) * | 2000-04-27 | 2008-12-31 | Abbott Lab | Diazabicyclic central nervous system active agents |
US6809105B2 (en) | 2000-04-27 | 2004-10-26 | Abbott Laboratories | Diazabicyclic central nervous system active agents |
EP1289996B1 (en) * | 2000-05-25 | 2005-04-06 | Targacept, Inc. | Heteroaryldiazabicycloalkanes as nicotinic cholinergic receptor ligands |
US6440970B1 (en) | 2000-05-25 | 2002-08-27 | Targacept, Inc. | Pharmaceutical compositions and methods for use |
US7060699B2 (en) * | 2000-07-04 | 2006-06-13 | Neurosearch A/S | Aryl and heteroaryl diazabicycloalkanes, their preparation and use |
US6624167B1 (en) | 2000-08-04 | 2003-09-23 | Targacept, Inc. | Pharmaceutical compositions and methods for use |
US7329754B2 (en) * | 2001-03-02 | 2008-02-12 | Neurosearch A/S | 2,5-diazabicyclo[2.2.1]heptane derivatives |
WO2002096911A1 (en) * | 2001-06-01 | 2002-12-05 | Neurosearch A/S | Novel heteroaryl-diazabicyclo-alkanes as cns-modulators |
AR036041A1 (es) * | 2001-06-12 | 2004-08-04 | Upjohn Co | Compuestos aromaticos heterociclicos sustituidos con quinuclidina y composiciones farmaceuticas que los contienen |
US7390813B1 (en) | 2001-12-21 | 2008-06-24 | Xenon Pharmaceuticals Inc. | Pyridylpiperazines and aminonicotinamides and their use as therapeutic agents |
WO2003062235A1 (en) * | 2002-01-17 | 2003-07-31 | Eli Lilly And Company | Modulators of acetylcholine receptors |
DK1506200T3 (da) | 2002-05-07 | 2007-04-10 | Neurosearch As | Diazabicykliske biarylderivater |
US7135484B2 (en) | 2002-08-14 | 2006-11-14 | Abbott Laboratories | Azabicyclic compounds are central nervous system active agents |
US20040242641A1 (en) * | 2003-05-27 | 2004-12-02 | Buckley Michael J. | (1S,5S)-3-(5,6-dichloro-3-pyridinyl)-3,6-diazabicyclo[3.2.0]heptane is an effective analgesic agent |
BRPI0413059A (pt) | 2003-07-29 | 2006-10-31 | Xenon Pharmaceuticals Inc | derivados de piridila e seu uso como agentes terapêuticos |
DK1648874T3 (da) | 2003-07-30 | 2012-01-23 | Xenon Pharmaceuticals Inc | Piperazinderivater samt deres anvendelse som terapeutisk aktive stoffer |
US20050065178A1 (en) * | 2003-09-19 | 2005-03-24 | Anwer Basha | Substituted diazabicycloakane derivatives |
US7399765B2 (en) | 2003-09-19 | 2008-07-15 | Abbott Laboratories | Substituted diazabicycloalkane derivatives |
WO2005054201A1 (en) | 2003-11-20 | 2005-06-16 | Janssen Pharmaceutica N.V. | 6-alkenyl and 6-phenylalkyl substituted 2-quinolinones and 2-quinoxalinones as poly(adp-ribose) polymerase inhibitors |
CN1882549B (zh) | 2003-11-20 | 2011-02-23 | 詹森药业有限公司 | 用作聚(adp-核糖)聚合酶抑制剂的7-苯基烷基取代的2-喹啉酮和2-喹喔啉酮 |
DE602004010299T2 (de) * | 2003-12-22 | 2008-09-18 | Memory Pharmaceuticals Corp. | Indole, 1h-indazole, 1,2-benzisoxazole und 1,2-benzisothiazole und deren herstellung und anwendungen |
US20050171079A1 (en) * | 2004-02-04 | 2005-08-04 | Schrimpf Michael R. | Amino-substituted tricyclic derivatives and methods of use |
US7365193B2 (en) | 2004-02-04 | 2008-04-29 | Abbott Laboratories | Amino-substituted tricyclic derivatives and methods of use |
JP2007520526A (ja) | 2004-02-04 | 2007-07-26 | ノイロサーチ アクティーゼルスカブ | コリン作動性受容体モジュレーターとしてのジアザビシクロアリール誘導体 |
ATE487716T1 (de) | 2004-04-22 | 2010-11-15 | Memory Pharm Corp | Indole, 1h-indazole, 1,2-benzisoxazole, 1,2- benzoisothiazole, deren herstellung und verwendungen |
ITMI20040954A1 (it) * | 2004-05-12 | 2004-08-12 | Univ Degli Studi Milano | Derivati del 3,6-diazabiciclo 3.1.i.eptano ad attivita' analgesica |
EP1763523B1 (en) | 2004-06-30 | 2013-03-20 | Janssen Pharmaceutica NV | Quinazolinedione derivatives as parp inhibitors |
KR101286969B1 (ko) | 2004-06-30 | 2013-07-23 | 얀센 파마슈티카 엔.브이. | Parp 저해제로서의 퀴나졸리논 유도체 |
MXPA06014542A (es) * | 2004-06-30 | 2007-03-23 | Janssen Pharmaceutica Nv | Derivados de ftalazina como inhibidores de poli(adp-ribosa) polimerasa-i. |
AU2005284908B2 (en) | 2004-09-13 | 2011-12-08 | Morningside Venture Investments Limited | Biosynchronous transdermal drug delivery |
AR051091A1 (es) | 2004-09-20 | 2006-12-20 | Xenon Pharmaceuticals Inc | Derivados heterociclicos y su uso como inhibidores de la estearoil-coa desaturasa |
CN101083982A (zh) | 2004-09-20 | 2007-12-05 | 泽农医药公司 | 用于治疗硬脂酰CoA去饱和酶介导的疾病的杂环衍生物 |
CN101083992A (zh) | 2004-09-20 | 2007-12-05 | 泽农医药公司 | 抑制人硬脂酰CoA去饱和酶的哒嗪衍生物 |
WO2006034441A1 (en) | 2004-09-20 | 2006-03-30 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as stearoyl-coa desaturase inhibitors |
JP4958786B2 (ja) | 2004-09-20 | 2012-06-20 | ゼノン・ファーマシューティカルズ・インコーポレイテッド | 複素環誘導体および治療薬としてのそれらの使用 |
AU2005329423A1 (en) | 2004-09-20 | 2006-09-28 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as stearoyl-CoA desaturase inhibitors |
TW200626138A (en) | 2004-09-20 | 2006-08-01 | Xenon Pharmaceuticals Inc | Heterocyclic derivatives and their use as therapeutic agents |
ATE481407T1 (de) | 2005-02-16 | 2010-10-15 | Neurosearch As | Neue diazabicyclische arylderivate und medizinische verwendung dafür |
US7662812B2 (en) | 2005-02-16 | 2010-02-16 | Neurosearch A/S | Diazabicyclic aryl derivatives and their use as chinolinergic ligands at nicotinic acetylcholine receptors |
MX2007015216A (es) | 2005-06-03 | 2008-02-22 | Xenon Pharmaceuticals Inc | Derivados de aminotiazol y sus usos como agentes terapeuticos. |
NZ567048A (en) * | 2005-12-06 | 2010-12-24 | Neurosearch As | Novel diazabicyclic aryl derivatives and their medical use |
CN101448828B (zh) * | 2006-02-10 | 2011-12-07 | 神经研究公司 | 作为烟碱性乙酰胆碱受体激动剂的3-杂芳基-3,9-二氮杂双环[3.3.1]壬烷衍生物 |
WO2007090888A1 (en) | 2006-02-10 | 2007-08-16 | Neurosearch A/S | 3-heteroaryl- 3,9-diazabicyclo[3.3.1]nonane derivatives as nicotinic acetylcholine receptor agonists |
AU2007213670A1 (en) * | 2006-02-10 | 2007-08-16 | Neurosearch A/S | 3,9-diazabicyclo[3.3.1]nonane derivatives and their use as monoamine neurotransmitter re-uptake inhibitors |
AU2007213669A1 (en) | 2006-02-10 | 2007-08-16 | Neurosearch A/S | 3,9-diazabicyclo[3.3.1]nonane derivatives and their use as monoamine neurotransmitter re-uptake inhibitors |
WO2007093601A1 (en) * | 2006-02-14 | 2007-08-23 | Neurosearch A/S | 3, 9-diazabicyclo(3.3.1)non-3-yl-aryl methanone derivatives as nicotinic acetylcholine receptor agonists |
US20090075983A1 (en) * | 2006-02-14 | 2009-03-19 | Dan Peters | Novel Diazabicycloalkane Derivatives and Their Medical Use |
CA2647830C (en) * | 2006-05-19 | 2016-02-09 | Abbott Laboratories | Central nervous system active fused bicycloheterocycle substituted azabicyclic alkane derivatives |
EP2029607A1 (en) | 2006-05-23 | 2009-03-04 | NeuroSearch A/S | Novel 8,10-diaza-bicycloý4.3.1¨decane derivatives and their medical use |
WO2008008517A2 (en) | 2006-07-14 | 2008-01-17 | Merck & Co., Inc. | Bridged diazepan orexin receptor antagonists |
US8076350B2 (en) | 2006-12-22 | 2011-12-13 | Abbott Laboratories | Spirocyclic azaadamantane derivatives and methods of use |
US8299256B2 (en) | 2007-03-08 | 2012-10-30 | Janssen Pharmaceutica Nv | Quinolinone derivatives as PARP and TANK inhibitors |
CN103977003A (zh) | 2007-04-02 | 2014-08-13 | 帕金森氏病研究院 | 用于降低治疗的副作用的方法和组合物 |
AU2008255005B2 (en) * | 2007-05-18 | 2013-05-02 | Merck Sharp & Dohme Corp. | OXO bridged diazepan orexin receptor antagonists |
ES2448870T3 (es) | 2007-10-26 | 2014-03-17 | Janssen Pharmaceutica, N.V. | Derivados de quinolina como inhibidores de PARP |
WO2009081246A2 (en) * | 2007-12-19 | 2009-07-02 | Pfizer Inc. | Bicyclic diamines as nicotinic receptor agonists |
ES2529545T3 (es) | 2008-03-27 | 2015-02-23 | Janssen Pharmaceutica, N.V. | Tetrahidrofenantridinonas y tetrahidrociclopentaquinolinonas como inhibidores de la polimerización de tubulina y PARP |
CA2716088C (en) | 2008-03-27 | 2017-03-07 | Eddy Jean Edgard Freyne | Quinazolinone derivatives as tubulin polymerization inhibitors |
US8148408B2 (en) | 2008-05-09 | 2012-04-03 | Abbott Laboratories | Selective substituted pyridine ligands for neuronal nicotinic receptors |
TW201004963A (en) * | 2008-07-03 | 2010-02-01 | Targacept Inc | Derivatives of oxabispidine as neuronal nicotinic acetylcholine receptor ligands |
AU2009303545A1 (en) * | 2008-10-14 | 2010-04-22 | Psychogenics, Inc | Nicotinic acetylcholine receptor ligands and the uses thereof |
KR101925971B1 (ko) * | 2011-01-28 | 2018-12-06 | 에스케이바이오팜 주식회사 | 피리돈 유도체 및 이를 포함하는 약학적 조성물 |
WO2013016160A1 (en) * | 2011-07-26 | 2013-01-31 | Merck Sharp & Dohme Corp. | NOVEL IMIDAZO[1,2-A]PYRAZINE DERIVATIVES AS mTOR INHIBITORS |
WO2013050938A1 (en) * | 2011-10-04 | 2013-04-11 | Actelion Pharmaceuticals Ltd | 3,7-diazabicyclo[3.3.1]nonane and 9-oxa-3,7-diazabicyclo[3.3.1]nonane derivatives |
US20150031675A1 (en) * | 2012-02-02 | 2015-01-29 | Targacept, Inc. | Diazabicyclo[3.3.1]nonanes, methods of synthesis, and uses thereof |
CN102952134B (zh) * | 2012-12-05 | 2015-01-07 | 苏州药明康德检测检验有限责任公司 | 含二氟甲基的金雀花碱衍生物及制备方法和抗癌作用研究 |
WO2016054123A1 (en) | 2014-09-30 | 2016-04-07 | Lightner Derek | Methods of producing heteropolycycles via bis-epoxidation |
CA2974324A1 (en) | 2015-01-28 | 2016-08-04 | Zita S. Netzel | Drug delivery methods and systems |
US11285306B2 (en) | 2017-01-06 | 2022-03-29 | Morningside Venture Investments Limited | Transdermal drug delivery devices and methods |
US20180311238A1 (en) * | 2017-04-28 | 2018-11-01 | Saniona A/S | Selective Agonist Of a6 Containing nAChRs |
AU2019279884A1 (en) | 2018-05-29 | 2020-12-10 | Morningside Venture Investments Limited | Drug delivery methods and systems |
AR117169A1 (es) | 2018-11-28 | 2021-07-14 | Bayer Ag | (tio)amidas de piridazina como compuestos fungicidas |
CA3124013A1 (en) | 2018-12-20 | 2020-06-25 | Bayer Aktiengesellschaft | Heterocyclyl pyridazine as fungicidal compounds |
US20230165252A1 (en) | 2020-05-27 | 2023-06-01 | Bayer Aktiengesellschaft | Active compound combinations |
CA3187297A1 (en) | 2020-06-18 | 2021-12-23 | Bayer Aktiengesellschaft | Active compound combinations |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5478939A (en) * | 1994-07-20 | 1995-12-26 | American Cyanamid Company | (R,R) and (S,S) 2,5-diazabicyclo [2,2,1]heptane derivatives |
RU2186780C2 (ru) * | 1997-05-30 | 2002-08-10 | Ньюросерч А/С | Производное 8-азабицикло [3.2.1]окт-2-ена, способы его получения, фармацевтическая композиция |
AU736798B2 (en) * | 1997-05-30 | 2001-08-02 | Neurosearch A/S | 9-Azabicyclo(3.3.1)non-2-ene and nonane derivatives as cholinergic ligands at nicotinic ACh receptors |
FR2786769B1 (fr) * | 1998-12-04 | 2002-10-25 | Synthelabo | Derives de 2,5-diazabicyclo[2.2.1]heptane, leur preparation et leur application en therapeutique |
-
2000
- 2000-01-25 CN CNA2004100974823A patent/CN1636996A/zh active Pending
- 2000-01-25 CA CA002361525A patent/CA2361525C/en not_active Expired - Fee Related
- 2000-01-25 ES ES03017562T patent/ES2305373T3/es not_active Expired - Lifetime
- 2000-01-25 AT AT03017562T patent/ATE394401T1/de not_active IP Right Cessation
- 2000-01-25 PT PT00906998T patent/PT1147112E/pt unknown
- 2000-01-25 DE DE60006213T patent/DE60006213T2/de not_active Expired - Lifetime
- 2000-01-25 WO PCT/US2000/001620 patent/WO2000044755A1/en not_active Application Discontinuation
- 2000-01-25 NZ NZ512884A patent/NZ512884A/xx unknown
- 2000-01-25 AU AU28569/00A patent/AU773795B2/en not_active Ceased
- 2000-01-25 EP EP03017562A patent/EP1359152B1/en not_active Expired - Lifetime
- 2000-01-25 AT AT00906998T patent/ATE253067T1/de active
- 2000-01-25 TR TR2001/02162T patent/TR200102162T2/xx unknown
- 2000-01-25 KR KR1020017009420A patent/KR20010101725A/ko not_active Application Discontinuation
- 2000-01-25 EP EP00906998A patent/EP1147112B1/en not_active Expired - Lifetime
- 2000-01-25 BR BR0007664-3A patent/BR0007664A/pt not_active IP Right Cessation
- 2000-01-25 DK DK00906998T patent/DK1147112T3/da active
- 2000-01-25 HU HU0200332A patent/HUP0200332A3/hu unknown
- 2000-01-25 IL IL14434000A patent/IL144340A0/xx unknown
- 2000-01-25 CZ CZ20012716A patent/CZ20012716A3/cs unknown
- 2000-01-25 JP JP2000596011A patent/JP4676062B2/ja not_active Expired - Fee Related
- 2000-01-25 ES ES00906998T patent/ES2209825T3/es not_active Expired - Lifetime
- 2000-01-25 CN CN00805544A patent/CN1345320A/zh active Pending
- 2000-01-25 SK SK1069-2001A patent/SK10692001A3/sk unknown
- 2000-01-25 DE DE60038823T patent/DE60038823D1/de not_active Expired - Lifetime
- 2000-01-26 CO CO00004294A patent/CO5150231A1/es unknown
- 2000-01-28 AR ARP000100393A patent/AR034538A1/es not_active Application Discontinuation
- 2000-03-01 TW TW091133012A patent/TW200300021A/zh unknown
-
2001
- 2001-07-16 ZA ZA200105835A patent/ZA200105835B/en unknown
- 2001-07-30 NO NO20013731A patent/NO20013731L/no not_active Application Discontinuation
- 2001-08-22 BG BG105836A patent/BG105836A/xx unknown
-
2002
- 2002-04-18 HK HK02102948.7A patent/HK1043116B/zh not_active IP Right Cessation
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
ZA200105835B (en) | Diazabicyclic derivatives as nicotinic acetylcholine receptor ligands. | |
US11001561B2 (en) | Pyrimidinone derivatives as SHP2 antagonists | |
TWI323733B (en) | Diazabicyclic central nervous system active agents | |
RU2387647C2 (ru) | Применение n-арилдиазаспироциклических соединений для лечения зависимостей | |
US8119635B2 (en) | Diazabicyclic central nervous system active agents | |
AU2008258187B2 (en) | Arylvinylazacycloalkane compounds and methods of preparation and use thereof | |
AU2012301953C1 (en) | Antibacterial compounds and methods for use | |
JP2007269811A (ja) | 化学的シナプス伝達の制御に有用なフロピリジン、チエノピリジン、ピロロピリジンおよび関連するピリミジン、ピリダジンおよびトリアジン化合物 | |
US20030225268A1 (en) | Diazabicyclic CNS active agents | |
WO2013142269A1 (en) | Imidazotriazinone compounds | |
KR20150063030A (ko) | 치환된 피리딘 아졸로피리미딘-5-(6h)-온 화합물 | |
EP2727604A1 (en) | Antipruritic agent | |
EP0973777A1 (en) | Furopyridine, thienopyridine, pyrrolopyridine and related pyrimidine, pyridazine and triazine compounds useful in controlling chemical synaptic transmission | |
DE69813536T2 (de) | 7a-substituierte hexahydro-1h-pyrrolizinverbindungen verwendbar zur kontrolle von chemische synaptische übertragung | |
ZA200208274B (en) | Diazabicyclic central nervous system active agents. | |
MXPA99007626A (es) | Compuestos de hexahidro-1h-pirrolizina 7a-heterociclo-substituidos utiles para controlar la transmision sinaptica quimica |