DE602004006767T2 - Nichtamidnonane - Google Patents
Nichtamidnonane Download PDFInfo
- Publication number
- DE602004006767T2 DE602004006767T2 DE602004006767T DE602004006767T DE602004006767T2 DE 602004006767 T2 DE602004006767 T2 DE 602004006767T2 DE 602004006767 T DE602004006767 T DE 602004006767T DE 602004006767 T DE602004006767 T DE 602004006767T DE 602004006767 T2 DE602004006767 T2 DE 602004006767T2
- Authority
- DE
- Germany
- Prior art keywords
- diazabicyclo
- nonane
- ylmethyl
- methane
- phenyl
- 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.)
- Expired - Fee Related
Links
- 150000001875 compounds Chemical class 0.000 claims abstract description 100
- 238000000034 method Methods 0.000 claims abstract description 33
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 21
- 150000003839 salts Chemical class 0.000 claims abstract description 16
- 201000010099 disease Diseases 0.000 claims abstract description 13
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 13
- 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 abstract description 6
- 230000008569 process Effects 0.000 claims abstract description 5
- 238000011282 treatment Methods 0.000 claims description 31
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 28
- 239000003814 drug Substances 0.000 claims description 25
- 238000011321 prophylaxis Methods 0.000 claims description 23
- 238000004519 manufacturing process Methods 0.000 claims description 21
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 18
- -1 benzoimidazolyl Chemical group 0.000 claims description 17
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 9
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 8
- 208000035475 disorder Diseases 0.000 claims description 8
- 208000028017 Psychotic disease Diseases 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 claims description 7
- 125000004076 pyridyl group Chemical group 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 208000024827 Alzheimer disease Diseases 0.000 claims description 6
- 208000019901 Anxiety disease Diseases 0.000 claims description 6
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 6
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- 208000002193 Pain Diseases 0.000 claims description 6
- 208000018737 Parkinson disease Diseases 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- 208000000323 Tourette Syndrome Diseases 0.000 claims description 6
- 208000016620 Tourette disease Diseases 0.000 claims description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 6
- 230000036506 anxiety Effects 0.000 claims description 6
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
- 201000000980 schizophrenia Diseases 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 208000000044 Amnesia Diseases 0.000 claims description 5
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- 208000019888 Circadian rhythm sleep disease Diseases 0.000 claims description 5
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- 208000012902 Nervous system disease Diseases 0.000 claims description 5
- 208000025966 Neurological disease Diseases 0.000 claims description 5
- 201000006704 Ulcerative Colitis Diseases 0.000 claims description 5
- 208000028683 bipolar I disease Diseases 0.000 claims description 5
- 230000001713 cholinergic effect Effects 0.000 claims description 5
- 230000000694 effects Effects 0.000 claims description 5
- 208000033915 jet lag type circadian rhythm sleep disease Diseases 0.000 claims description 5
- 230000006984 memory degeneration Effects 0.000 claims description 5
- 208000023060 memory loss Diseases 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 5
- 230000036407 pain Effects 0.000 claims description 5
- 210000000225 synapse Anatomy 0.000 claims description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- XJIRVFAJKTXNCO-UHFFFAOYSA-N 4-[(6-phenylpyridin-2-yl)methyl]-1,4-diazabicyclo[3.2.2]nonane Chemical compound C1CN(CC2)CCC2N1CC(N=1)=CC=CC=1C1=CC=CC=C1 XJIRVFAJKTXNCO-UHFFFAOYSA-N 0.000 claims description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 4
- 201000004311 Gilles de la Tourette syndrome Diseases 0.000 claims description 4
- 208000023105 Huntington disease Diseases 0.000 claims description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 201000003723 learning disability Diseases 0.000 claims description 4
- 230000004770 neurodegeneration Effects 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- XYDWNLYPKBUXEC-UHFFFAOYSA-N 4-[(6-bromopyridin-2-yl)methyl]-1,4-diazabicyclo[3.2.2]nonane Chemical compound BrC1=CC=CC(CN2C3CCN(CC3)CC2)=N1 XYDWNLYPKBUXEC-UHFFFAOYSA-N 0.000 claims description 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 125000002541 furyl group Chemical group 0.000 claims description 3
- 239000012280 lithium aluminium hydride Substances 0.000 claims description 3
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- UBQRZXFQKHPJLR-UHFFFAOYSA-N 2-(1,4-diazabicyclo[3.2.2]nonan-4-ylmethyl)-1,3-benzothiazole Chemical compound N=1C2=CC=CC=C2SC=1CN1CCN2CCC1CC2 UBQRZXFQKHPJLR-UHFFFAOYSA-N 0.000 claims description 2
- LNRJGAIONKZYFP-UHFFFAOYSA-N 2-(1,4-diazabicyclo[3.2.2]nonan-4-ylmethyl)-1,3-thiazole Chemical compound C1CN(CC2)CCC2N1CC1=NC=CS1 LNRJGAIONKZYFP-UHFFFAOYSA-N 0.000 claims description 2
- VINNGRZRDRNSNC-UHFFFAOYSA-N 2-(1,4-diazabicyclo[3.2.2]nonan-4-ylmethyl)-1-methylbenzimidazole Chemical compound N=1C2=CC=CC=C2N(C)C=1CN1CCN2CCC1CC2 VINNGRZRDRNSNC-UHFFFAOYSA-N 0.000 claims description 2
- REFQQYQNWHWHQB-UHFFFAOYSA-N 2-(1,4-diazabicyclo[3.2.2]nonan-4-ylmethyl)-4-phenyl-1,3-thiazole Chemical compound C1CN(CC2)CCC2N1CC(SC=1)=NC=1C1=CC=CC=C1 REFQQYQNWHWHQB-UHFFFAOYSA-N 0.000 claims description 2
- FBVNNGJZOTXVEF-UHFFFAOYSA-N 2-(1,4-diazabicyclo[3.2.2]nonan-4-ylmethyl)quinoline Chemical compound C=1C=C2C=CC=CC2=NC=1CN1CCN2CCC1CC2 FBVNNGJZOTXVEF-UHFFFAOYSA-N 0.000 claims description 2
- IJBCOAKSOSCNOI-UHFFFAOYSA-N 2-bromo-5-(1,4-diazabicyclo[3.2.2]nonan-4-ylmethyl)-1,3-thiazole Chemical compound S1C(Br)=NC=C1CN1C(CC2)CCN2CC1 IJBCOAKSOSCNOI-UHFFFAOYSA-N 0.000 claims description 2
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- PCCGBIBILVNICT-UHFFFAOYSA-N 3-(1,4-diazabicyclo[3.2.2]nonan-4-ylmethyl)quinoline Chemical compound C=1N=C2C=CC=CC2=CC=1CN1CCN2CCC1CC2 PCCGBIBILVNICT-UHFFFAOYSA-N 0.000 claims description 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- DNZPQWHJYCWNHR-UHFFFAOYSA-N 4-(1,4-diazabicyclo[3.2.2]nonan-4-ylmethyl)-2-phenyl-1,3-thiazole Chemical compound C1CN(CC2)CCC2N1CC(N=1)=CSC=1C1=CC=CC=C1 DNZPQWHJYCWNHR-UHFFFAOYSA-N 0.000 claims description 2
- YCYFEVOWCCVAIH-UHFFFAOYSA-N 4-(1-benzofuran-2-ylmethyl)-1,4-diazabicyclo[3.2.2]nonane Chemical compound C=1C2=CC=CC=C2OC=1CN1CCN2CCC1CC2 YCYFEVOWCCVAIH-UHFFFAOYSA-N 0.000 claims description 2
- JQYJGTWBTCVOPV-UHFFFAOYSA-N 4-(1-benzothiophen-3-ylmethyl)-1,4-diazabicyclo[3.2.2]nonane Chemical compound C=1SC2=CC=CC=C2C=1CN1CCN2CCC1CC2 JQYJGTWBTCVOPV-UHFFFAOYSA-N 0.000 claims description 2
- CIRJBIVVIIOCFQ-UHFFFAOYSA-N 4-(2-phenylmethoxyethyl)-1,4-diazabicyclo[3.2.2]nonane Chemical compound C1CN(CC2)CCC2N1CCOCC1=CC=CC=C1 CIRJBIVVIIOCFQ-UHFFFAOYSA-N 0.000 claims description 2
- LGWAFBWTSXBLIZ-UHFFFAOYSA-N 4-(3-phenylprop-2-enyl)-1,4-diazabicyclo[3.2.2]nonane Chemical compound C1CN(CC2)CCC2N1CC=CC1=CC=CC=C1 LGWAFBWTSXBLIZ-UHFFFAOYSA-N 0.000 claims description 2
- DAKWUNBEVQWFQO-UHFFFAOYSA-N 4-(3-phenylprop-2-ynyl)-1,4-diazabicyclo[3.2.2]nonane Chemical compound C1CN(CC2)CCC2N1CC#CC1=CC=CC=C1 DAKWUNBEVQWFQO-UHFFFAOYSA-N 0.000 claims description 2
- CBBFPWDAUGHFDQ-UHFFFAOYSA-N 4-(3-phenylpropyl)-1,4-diazabicyclo[3.2.2]nonane Chemical compound C1CN(CC2)CCC2N1CCCC1=CC=CC=C1 CBBFPWDAUGHFDQ-UHFFFAOYSA-N 0.000 claims description 2
- LKPDYIBKLAVZRC-UHFFFAOYSA-N 4-(pyridin-2-ylmethyl)-1,4-diazabicyclo[3.2.2]nonane Chemical compound C1CN(CC2)CCC2N1CC1=CC=CC=N1 LKPDYIBKLAVZRC-UHFFFAOYSA-N 0.000 claims description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims description 2
- OMWSHMFHPDFZGS-UHFFFAOYSA-N 4-[(3-methyl-5-phenylthiophen-2-yl)methyl]-1,4-diazabicyclo[3.2.2]nonane Chemical compound S1C(CN2C3CCN(CC3)CC2)=C(C)C=C1C1=CC=CC=C1 OMWSHMFHPDFZGS-UHFFFAOYSA-N 0.000 claims description 2
- DPZPYDHIXALGSA-UHFFFAOYSA-N 4-[(3-phenylphenyl)methyl]-1,4-diazabicyclo[3.2.2]nonane Chemical compound C1CN(CC2)CCC2N1CC(C=1)=CC=CC=1C1=CC=CC=C1 DPZPYDHIXALGSA-UHFFFAOYSA-N 0.000 claims description 2
- DGWPBBPYBWXPMF-UHFFFAOYSA-N 4-[(4-bromofuran-2-yl)methyl]-1,4-diazabicyclo[3.2.2]nonane Chemical compound BrC1=COC(CN2C3CCN(CC3)CC2)=C1 DGWPBBPYBWXPMF-UHFFFAOYSA-N 0.000 claims description 2
- KUAYKLXQFSZOPP-UHFFFAOYSA-N 4-[(4-bromothiophen-2-yl)methyl]-1,4-diazabicyclo[3.2.2]nonane Chemical compound BrC1=CSC(CN2C3CCN(CC3)CC2)=C1 KUAYKLXQFSZOPP-UHFFFAOYSA-N 0.000 claims description 2
- RPEKOGDSVCJAKQ-UHFFFAOYSA-N 4-[(4-phenylpyridin-2-yl)methyl]-1,4-diazabicyclo[3.2.2]nonane Chemical compound C1CN(CC2)CCC2N1CC(N=CC=1)=CC=1C1=CC=CC=C1 RPEKOGDSVCJAKQ-UHFFFAOYSA-N 0.000 claims description 2
- VLCXOFDFQNSQAJ-UHFFFAOYSA-N 4-[(4-phenylthiophen-2-yl)methyl]-1,4-diazabicyclo[3.2.2]nonane Chemical compound C1CN(CC2)CCC2N1CC(SC=1)=CC=1C1=CC=CC=C1 VLCXOFDFQNSQAJ-UHFFFAOYSA-N 0.000 claims description 2
- LXKVUNZKWYSOOR-UHFFFAOYSA-N 4-[(4-pyridin-2-ylphenyl)methyl]-1,4-diazabicyclo[3.2.2]nonane Chemical compound C1CN(CC2)CCC2N1CC(C=C1)=CC=C1C1=CC=CC=N1 LXKVUNZKWYSOOR-UHFFFAOYSA-N 0.000 claims description 2
- GZSVFOHRTMTDLU-UHFFFAOYSA-N 4-[(4-pyridin-2-ylthiophen-2-yl)methyl]-1,4-diazabicyclo[3.2.2]nonane Chemical compound C1CN(CC2)CCC2N1CC(SC=1)=CC=1C1=CC=CC=N1 GZSVFOHRTMTDLU-UHFFFAOYSA-N 0.000 claims description 2
- JJTBJROJFUAOAA-UHFFFAOYSA-N 4-[(4-pyridin-3-ylthiophen-2-yl)methyl]-1,4-diazabicyclo[3.2.2]nonane Chemical compound C1CN(CC2)CCC2N1CC(SC=1)=CC=1C1=CC=CN=C1 JJTBJROJFUAOAA-UHFFFAOYSA-N 0.000 claims description 2
- YCAHNRCVGUBAOA-UHFFFAOYSA-N 4-[(4-pyridin-4-ylthiophen-2-yl)methyl]-1,4-diazabicyclo[3.2.2]nonane Chemical compound C1CN(CC2)CCC2N1CC(SC=1)=CC=1C1=CC=NC=C1 YCAHNRCVGUBAOA-UHFFFAOYSA-N 0.000 claims description 2
- VLEYBICLJJPRTG-UHFFFAOYSA-N 4-[(5-bromothiophen-2-yl)methyl]-1,4-diazabicyclo[3.2.2]nonane Chemical compound S1C(Br)=CC=C1CN1C(CC2)CCN2CC1 VLEYBICLJJPRTG-UHFFFAOYSA-N 0.000 claims description 2
- SYCWDENGJYVOJV-UHFFFAOYSA-N 4-[(5-phenylfuran-2-yl)methyl]-1,4-diazabicyclo[3.2.2]nonane Chemical compound C1CN(CC2)CCC2N1CC(O1)=CC=C1C1=CC=CC=C1 SYCWDENGJYVOJV-UHFFFAOYSA-N 0.000 claims description 2
- WICAHOKENBNMDX-UHFFFAOYSA-N 4-[(5-phenylpyridin-2-yl)methyl]-1,4-diazabicyclo[3.2.2]nonane Chemical compound C1CN(CC2)CCC2N1CC(N=C1)=CC=C1C1=CC=CC=C1 WICAHOKENBNMDX-UHFFFAOYSA-N 0.000 claims description 2
- SUPMGNMPUCWEOY-UHFFFAOYSA-N 4-[(5-pyridin-2-ylthiophen-2-yl)methyl]-1,4-diazabicyclo[3.2.2]nonane Chemical compound C1CN(CC2)CCC2N1CC(S1)=CC=C1C1=CC=CC=N1 SUPMGNMPUCWEOY-UHFFFAOYSA-N 0.000 claims description 2
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- RVYLILSHTMEGAA-UHFFFAOYSA-N 4-[[4-(4-bromophenyl)sulfanylphenyl]methyl]-1,4-diazabicyclo[3.2.2]nonane Chemical compound C1=CC(Br)=CC=C1SC(C=C1)=CC=C1CN1C(CC2)CCN2CC1 RVYLILSHTMEGAA-UHFFFAOYSA-N 0.000 claims description 2
- MYMLUBIRFYEEJA-UHFFFAOYSA-N 4-[[4-(4-chlorophenyl)phenyl]methyl]-1,4-diazabicyclo[3.2.2]nonane Chemical compound C1=CC(Cl)=CC=C1C(C=C1)=CC=C1CN1C(CC2)CCN2CC1 MYMLUBIRFYEEJA-UHFFFAOYSA-N 0.000 claims description 2
- VQLLTSIHENQOJI-UHFFFAOYSA-N 4-[[4-[3-(trifluoromethyl)phenyl]phenyl]methyl]-1,4-diazabicyclo[3.2.2]nonane Chemical compound FC(F)(F)C1=CC=CC(C=2C=CC(CN3C4CCN(CC4)CC3)=CC=2)=C1 VQLLTSIHENQOJI-UHFFFAOYSA-N 0.000 claims description 2
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- XQQUUTAPJQCLAI-UHFFFAOYSA-N 5-(1,4-diazabicyclo[3.2.2]nonan-4-ylmethyl)-1,3-thiazole Chemical compound C1CN(CC2)CCC2N1CC1=CN=CS1 XQQUUTAPJQCLAI-UHFFFAOYSA-N 0.000 claims description 2
- LSUJLNVZDMUTAL-UHFFFAOYSA-N 5-(1,4-diazabicyclo[3.2.2]nonan-4-ylmethyl)-2-phenyl-1,3-thiazole Chemical compound C1CN(CC2)CCC2N1CC(S1)=CN=C1C1=CC=CC=C1 LSUJLNVZDMUTAL-UHFFFAOYSA-N 0.000 claims description 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 2
- 150000001540 azides Chemical class 0.000 claims description 2
- 125000004244 benzofuran-2-yl group Chemical group [H]C1=C(*)OC2=C([H])C([H])=C([H])C([H])=C12 0.000 claims description 2
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- 238000009835 boiling Methods 0.000 claims description 2
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- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
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- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002971 oxazolyl group Chemical group 0.000 claims description 2
- 125000004159 quinolin-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C([H])C(*)=NC2=C1[H] 0.000 claims description 2
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- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims 3
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- QIMMUPPBPVKWKM-UHFFFAOYSA-N 2-methylnaphthalene Chemical compound C1=CC=CC2=CC(C)=CC=C21 QIMMUPPBPVKWKM-UHFFFAOYSA-N 0.000 claims 1
- FTAWJHRUSIWHPL-UHFFFAOYSA-N 4-[(5-pyridin-4-ylthiophen-2-yl)methyl]-1,4-diazabicyclo[3.2.2]nonane Chemical compound C1CN(CC2)CCC2N1CC(S1)=CC=C1C1=CC=NC=C1 FTAWJHRUSIWHPL-UHFFFAOYSA-N 0.000 claims 1
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- 239000000543 intermediate Substances 0.000 abstract description 5
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- 239000002243 precursor Substances 0.000 abstract description 2
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- WPYJKGWLDJECQD-UHFFFAOYSA-N quinoline-2-carbaldehyde Chemical compound C1=CC=CC2=NC(C=O)=CC=C21 WPYJKGWLDJECQD-UHFFFAOYSA-N 0.000 description 1
- RYGIHSLRMNXWCN-UHFFFAOYSA-N quinoline-3-carbaldehyde Chemical compound C1=CC=CC2=CC(C=O)=CN=C21 RYGIHSLRMNXWCN-UHFFFAOYSA-N 0.000 description 1
- 230000006340 racemization Effects 0.000 description 1
- 238000007347 radical substitution reaction Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000006103 sulfonylation Effects 0.000 description 1
- 238000005694 sulfonylation reaction Methods 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 230000005062 synaptic transmission Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 239000004149 tartrazine Substances 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 125000005500 uronium group Chemical group 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
- A61K31/551—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having two nitrogen atoms, e.g. dilazep
-
- 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
- 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
- A61P25/04—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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
-
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- 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
- A61P25/34—Tobacco-abuse
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- General Chemical & Material Sciences (AREA)
- Psychiatry (AREA)
- Psychology (AREA)
- Pain & Pain Management (AREA)
- Addiction (AREA)
- Epidemiology (AREA)
- Anesthesiology (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Detergent Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US50666403P | 2003-09-26 | 2003-09-26 | |
| US506664P | 2003-09-26 | ||
| PCT/GB2004/004130 WO2005030777A1 (en) | 2003-09-26 | 2004-09-24 | Non-amide nonanes |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE602004006767D1 DE602004006767D1 (de) | 2007-07-12 |
| DE602004006767T2 true DE602004006767T2 (de) | 2008-02-07 |
Family
ID=34393184
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE602004006767T Expired - Fee Related DE602004006767T2 (de) | 2003-09-26 | 2004-09-24 | Nichtamidnonane |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US7482338B2 (enExample) |
| EP (1) | EP1673372B1 (enExample) |
| JP (1) | JP2007506723A (enExample) |
| AT (1) | ATE363484T1 (enExample) |
| DE (1) | DE602004006767T2 (enExample) |
| ES (1) | ES2285514T3 (enExample) |
| WO (1) | WO2005030777A1 (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20070015607A (ko) * | 2004-05-07 | 2007-02-05 | 메모리 파마슈티칼스 코포레이션 | 1ｈ-인다졸, 벤조티아졸, 1,2-벤조이속사졸,1,2-벤조이소티아졸, 및 크로몬 및 그의 제조법 및 용도 |
| US8846661B2 (en) * | 2009-06-19 | 2014-09-30 | Abbvie Inc. | Diazahomoadamantane derivatives and methods of use thereof |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4895943A (en) | 1988-10-25 | 1990-01-23 | Pfizer Inc. | Preparation of 1,4-diazabicyclo(3.2.2)nonane |
| US5679673A (en) * | 1992-09-24 | 1997-10-21 | The United States Of America, Represented By The Department Of Health And Human Services | Aralkyl bridged diazabicycloalkane derivatives for CNS disorders |
| 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 |
| 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 |
| US20020086871A1 (en) * | 2000-12-29 | 2002-07-04 | O'neill Brian Thomas | Pharmaceutical composition for the treatment of CNS and other disorders |
-
2004
- 2004-09-24 US US10/573,132 patent/US7482338B2/en not_active Expired - Fee Related
- 2004-09-24 JP JP2006527492A patent/JP2007506723A/ja active Pending
- 2004-09-24 EP EP04768673A patent/EP1673372B1/en not_active Expired - Lifetime
- 2004-09-24 AT AT04768673T patent/ATE363484T1/de not_active IP Right Cessation
- 2004-09-24 DE DE602004006767T patent/DE602004006767T2/de not_active Expired - Fee Related
- 2004-09-24 ES ES04768673T patent/ES2285514T3/es not_active Expired - Lifetime
- 2004-09-24 WO PCT/GB2004/004130 patent/WO2005030777A1/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| ATE363484T1 (de) | 2007-06-15 |
| US7482338B2 (en) | 2009-01-27 |
| US20070043031A1 (en) | 2007-02-22 |
| WO2005030777A1 (en) | 2005-04-07 |
| DE602004006767D1 (de) | 2007-07-12 |
| EP1673372A1 (en) | 2006-06-28 |
| JP2007506723A (ja) | 2007-03-22 |
| ES2285514T3 (es) | 2007-11-16 |
| EP1673372B1 (en) | 2007-05-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |