NO317094B1 - Heteroaryldiazasykloalkaner som kolinerge ligander i nikotinsyreacetylkolinreseptorer - Google Patents
Heteroaryldiazasykloalkaner som kolinerge ligander i nikotinsyreacetylkolinreseptorer Download PDFInfo
- Publication number
- NO317094B1 NO317094B1 NO20002132A NO20002132A NO317094B1 NO 317094 B1 NO317094 B1 NO 317094B1 NO 20002132 A NO20002132 A NO 20002132A NO 20002132 A NO20002132 A NO 20002132A NO 317094 B1 NO317094 B1 NO 317094B1
- Authority
- NO
- Norway
- Prior art keywords
- pyridyl
- homopiperazine
- methyl
- alkyl
- alkoxy
- Prior art date
Links
- 108010009685 Cholinergic Receptors Proteins 0.000 title claims abstract description 25
- 102000034337 acetylcholine receptors Human genes 0.000 title claims abstract description 25
- 239000003446 ligand Substances 0.000 title abstract description 3
- 230000001713 cholinergic effect Effects 0.000 title description 9
- QFBCQOXKGBYUSU-UHFFFAOYSA-M 2-acetyloxyethyl(trimethyl)azanium;pyridine-3-carboxylate Chemical compound [O-]C(=O)C1=CC=CN=C1.CC(=O)OCC[N+](C)(C)C QFBCQOXKGBYUSU-UHFFFAOYSA-M 0.000 title 1
- -1 methylenedioxy Chemical group 0.000 claims abstract description 104
- 150000001875 compounds Chemical class 0.000 claims abstract description 101
- 239000000203 mixture Substances 0.000 claims abstract description 91
- 150000003839 salts Chemical class 0.000 claims abstract description 37
- 230000000694 effects Effects 0.000 claims abstract description 13
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 12
- 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 8
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 45
- 201000010099 disease Diseases 0.000 claims description 32
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 30
- 238000002360 preparation method Methods 0.000 claims description 29
- 238000011282 treatment Methods 0.000 claims description 24
- 239000000126 substance Substances 0.000 claims description 18
- 208000002193 Pain Diseases 0.000 claims description 15
- 229960003512 nicotinic acid Drugs 0.000 claims description 15
- 235000001968 nicotinic acid Nutrition 0.000 claims description 15
- 239000011664 nicotinic acid Substances 0.000 claims description 15
- 230000036407 pain Effects 0.000 claims description 15
- 208000035475 disorder Diseases 0.000 claims description 12
- 150000004050 homopiperazines Chemical class 0.000 claims description 11
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 11
- 208000024827 Alzheimer disease Diseases 0.000 claims description 10
- 208000007271 Substance Withdrawal Syndrome Diseases 0.000 claims description 9
- 210000003169 central nervous system Anatomy 0.000 claims description 9
- 201000009032 substance abuse Diseases 0.000 claims description 9
- 210000001428 peripheral nervous system Anatomy 0.000 claims description 8
- 208000011117 substance-related disease Diseases 0.000 claims description 8
- 230000016160 smooth muscle contraction Effects 0.000 claims description 7
- JBOVXXZNZSULJJ-UHFFFAOYSA-N 1-pyridin-3-yl-1,4-diazepane Chemical compound C1CCNCCN1C1=CC=CN=C1 JBOVXXZNZSULJJ-UHFFFAOYSA-N 0.000 claims description 6
- 208000018737 Parkinson disease Diseases 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 230000007074 memory dysfunction Effects 0.000 claims description 6
- 230000000391 smoking effect Effects 0.000 claims description 6
- 231100000736 substance abuse Toxicity 0.000 claims description 6
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 claims description 5
- 241001465754 Metazoa Species 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 230000004770 neurodegeneration Effects 0.000 claims description 5
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 4
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 206010061218 Inflammation Diseases 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 230000004054 inflammatory process Effects 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- BINPOEPJNVMNPQ-UHFFFAOYSA-N 1-(3-methoxyphenyl)-1,4-diazepane Chemical compound COC1=CC=CC(N2CCNCCC2)=C1 BINPOEPJNVMNPQ-UHFFFAOYSA-N 0.000 claims description 3
- IZXOFIZUDVFRNW-UHFFFAOYSA-N 1-(3-nitrophenyl)-1,4-diazepane Chemical compound [O-][N+](=O)C1=CC=CC(N2CCNCCC2)=C1 IZXOFIZUDVFRNW-UHFFFAOYSA-N 0.000 claims description 3
- COTNBIFZSPMJRS-UHFFFAOYSA-N 1-(6-chloropyridin-3-yl)-1,4-diazepane Chemical compound C1=NC(Cl)=CC=C1N1CCNCCC1 COTNBIFZSPMJRS-UHFFFAOYSA-N 0.000 claims description 3
- RPXRPEUOPRESKS-UHFFFAOYSA-N 1-[5-(2-methoxyethoxy)pyridin-3-yl]-4-methyl-1,4-diazepane Chemical compound COCCOC1=CN=CC(N2CCN(C)CCC2)=C1 RPXRPEUOPRESKS-UHFFFAOYSA-N 0.000 claims description 3
- KZNRJQVKHPDDHZ-UHFFFAOYSA-N 1-benzyl-4-pyridin-3-yl-1,4-diazepane Chemical compound C=1C=CC=CC=1CN(CC1)CCCN1C1=CC=CN=C1 KZNRJQVKHPDDHZ-UHFFFAOYSA-N 0.000 claims description 3
- KYDXRBAEAVLVLQ-UHFFFAOYSA-N 1-methyl-4-(3-nitrophenyl)-1,4-diazepane Chemical compound C1CN(C)CCCN1C1=CC=CC([N+]([O-])=O)=C1 KYDXRBAEAVLVLQ-UHFFFAOYSA-N 0.000 claims description 3
- OXCIHVBAXPHXPZ-UHFFFAOYSA-N 1-methyl-4-pyridin-3-yl-1,4-diazepane Chemical compound C1CN(C)CCCN1C1=CC=CN=C1 OXCIHVBAXPHXPZ-UHFFFAOYSA-N 0.000 claims description 3
- 230000006735 deficit Effects 0.000 claims description 3
- IWUOSMQICZTQRU-UHFFFAOYSA-N 1-(3,6-dimethylpyrazin-2-yl)-1,4-diazepane Chemical compound CC1=CN=C(C)C(N2CCNCCC2)=N1 IWUOSMQICZTQRU-UHFFFAOYSA-N 0.000 claims description 2
- LUAQATCGUQIPIE-UHFFFAOYSA-N 1-(5,6-dimethoxypyridin-3-yl)-1,4-diazepane Chemical compound N1=C(OC)C(OC)=CC(N2CCNCCC2)=C1 LUAQATCGUQIPIE-UHFFFAOYSA-N 0.000 claims description 2
- HXIKXVVKUJGTHI-UHFFFAOYSA-N 1-(5-butoxypyridin-3-yl)-4-methyl-1,4-diazepane Chemical compound CCCCOC1=CN=CC(N2CCN(C)CCC2)=C1 HXIKXVVKUJGTHI-UHFFFAOYSA-N 0.000 claims description 2
- ZFKSPVBRKQTDIY-UHFFFAOYSA-N 1-(5-cyclopentyloxypyridin-3-yl)-1,4-diazepane Chemical compound C1CCCC1OC1=CN=CC(N2CCNCCC2)=C1 ZFKSPVBRKQTDIY-UHFFFAOYSA-N 0.000 claims description 2
- SYSCGYLNJIYMGG-UHFFFAOYSA-N 1-(5-cyclopentyloxypyridin-3-yl)-4-methyl-1,4-diazepane Chemical compound C1CN(C)CCCN1C1=CN=CC(OC2CCCC2)=C1 SYSCGYLNJIYMGG-UHFFFAOYSA-N 0.000 claims description 2
- DWHQCXVYIKBENZ-UHFFFAOYSA-N 1-(5-ethenoxypyridin-3-yl)-1,4-diazepane Chemical compound C=COC1=CN=CC(N2CCNCCC2)=C1 DWHQCXVYIKBENZ-UHFFFAOYSA-N 0.000 claims description 2
- RQXFSCANOMMTFZ-UHFFFAOYSA-N 1-(5-ethoxypyridin-3-yl)-1,4-diazepane Chemical compound CCOC1=CN=CC(N2CCNCCC2)=C1 RQXFSCANOMMTFZ-UHFFFAOYSA-N 0.000 claims description 2
- SXZCIPTVUFDPIG-UHFFFAOYSA-N 1-(5-ethoxypyridin-3-yl)-4-methyl-1,4-diazepane Chemical compound CCOC1=CN=CC(N2CCN(C)CCC2)=C1 SXZCIPTVUFDPIG-UHFFFAOYSA-N 0.000 claims description 2
- CTMLEMJMYZMVFW-UHFFFAOYSA-N 1-(5-ethynylpyridin-3-yl)-1,4-diazepane Chemical compound C#CC1=CN=CC(N2CCNCCC2)=C1 CTMLEMJMYZMVFW-UHFFFAOYSA-N 0.000 claims description 2
- XYAQZUBGSRIWRI-UHFFFAOYSA-N 1-(5-heptoxypyridin-3-yl)-1,4-diazepane Chemical compound CCCCCCCOC1=CN=CC(N2CCNCCC2)=C1 XYAQZUBGSRIWRI-UHFFFAOYSA-N 0.000 claims description 2
- SKBJCLBMYVXUAC-UHFFFAOYSA-N 1-(5-heptoxypyridin-3-yl)-4-methyl-1,4-diazepane Chemical compound CCCCCCCOC1=CN=CC(N2CCN(C)CCC2)=C1 SKBJCLBMYVXUAC-UHFFFAOYSA-N 0.000 claims description 2
- UHOWIRLRFQDWDJ-UHFFFAOYSA-N 1-(5-hexoxypyridin-3-yl)-1,4-diazepane Chemical compound CCCCCCOC1=CN=CC(N2CCNCCC2)=C1 UHOWIRLRFQDWDJ-UHFFFAOYSA-N 0.000 claims description 2
- QPKJBGOPBKHVNR-UHFFFAOYSA-N 1-(5-hexoxypyridin-3-yl)-4-methyl-1,4-diazepane Chemical compound CCCCCCOC1=CN=CC(N2CCN(C)CCC2)=C1 QPKJBGOPBKHVNR-UHFFFAOYSA-N 0.000 claims description 2
- CLRANNZHQRADST-UHFFFAOYSA-N 1-(5-methoxypyridin-3-yl)-1,4-diazepane Chemical compound COC1=CN=CC(N2CCNCCC2)=C1 CLRANNZHQRADST-UHFFFAOYSA-N 0.000 claims description 2
- UQIGCWXXDZIAON-UHFFFAOYSA-N 1-(5-methoxypyridin-3-yl)-4-methyl-1,4-diazepane Chemical compound COC1=CN=CC(N2CCN(C)CCC2)=C1 UQIGCWXXDZIAON-UHFFFAOYSA-N 0.000 claims description 2
- IWYDMTKGIWVZES-UHFFFAOYSA-N 1-(5-pentoxypyridin-3-yl)-1,4-diazepane Chemical compound CCCCCOC1=CN=CC(N2CCNCCC2)=C1 IWYDMTKGIWVZES-UHFFFAOYSA-N 0.000 claims description 2
- YAWZOEAWIFAGIV-UHFFFAOYSA-N 1-(5-phenylpyridin-3-yl)-1,4-diazepane Chemical compound C1CCNCCN1C1=CN=CC(C=2C=CC=CC=2)=C1 YAWZOEAWIFAGIV-UHFFFAOYSA-N 0.000 claims description 2
- LWFPJCHDKSLKOQ-UHFFFAOYSA-N 1-(5-propoxypyridin-3-yl)-1,4-diazepane Chemical compound CCCOC1=CN=CC(N2CCNCCC2)=C1 LWFPJCHDKSLKOQ-UHFFFAOYSA-N 0.000 claims description 2
- LZVFGIRZLQUNPB-UHFFFAOYSA-N 1-(5-pyridin-3-ylpyridin-3-yl)-1,4-diazepane Chemical compound C1CCNCCN1C1=CN=CC(C=2C=NC=CC=2)=C1 LZVFGIRZLQUNPB-UHFFFAOYSA-N 0.000 claims description 2
- KANJHLBZMCYLFW-UHFFFAOYSA-N 1-(5-thiophen-2-ylpyridin-3-yl)-1,4-diazepane Chemical compound C1CCNCCN1C1=CN=CC(C=2SC=CC=2)=C1 KANJHLBZMCYLFW-UHFFFAOYSA-N 0.000 claims description 2
- HCZRQDZSEJRDJS-UHFFFAOYSA-N 1-(6-chloropyrazin-2-yl)-1,4-diazepane Chemical compound ClC1=CN=CC(N2CCNCCC2)=N1 HCZRQDZSEJRDJS-UHFFFAOYSA-N 0.000 claims description 2
- SYCMNXTXRHUPAZ-UHFFFAOYSA-N 1-(6-methoxypyridin-3-yl)-1,4-diazepane Chemical compound C1=NC(OC)=CC=C1N1CCNCCC1 SYCMNXTXRHUPAZ-UHFFFAOYSA-N 0.000 claims description 2
- NDMXANRHRVRLQR-UHFFFAOYSA-N 1-(6-pyrrolidin-1-ylpyridin-3-yl)-1,4-diazepane Chemical compound C1CCCN1C1=CC=C(N2CCNCCC2)C=N1 NDMXANRHRVRLQR-UHFFFAOYSA-N 0.000 claims description 2
- RQXFSCANOMMTFZ-ZBJDZAJPSA-N 1-[5-(1,1,2,2,2-pentadeuterioethoxy)pyridin-3-yl]-1,4-diazepane Chemical compound [2H]C([2H])([2H])C([2H])([2H])OC1=CN=CC(N2CCNCCC2)=C1 RQXFSCANOMMTFZ-ZBJDZAJPSA-N 0.000 claims description 2
- KPRAXWCBFDDHSF-UHFFFAOYSA-N 1-[5-(1,4-diazepan-1-yl)pyridin-3-yl]indole Chemical compound C1CCNCCN1C1=CN=CC(N2C3=CC=CC=C3C=C2)=C1 KPRAXWCBFDDHSF-UHFFFAOYSA-N 0.000 claims description 2
- YVYLKKKASVLYEK-UHFFFAOYSA-N 1-[5-(2-ethoxyethoxy)pyridin-3-yl]-1,4-diazepane Chemical compound CCOCCOC1=CN=CC(N2CCNCCC2)=C1 YVYLKKKASVLYEK-UHFFFAOYSA-N 0.000 claims description 2
- SIPSUTQRUBWRRD-UHFFFAOYSA-N 1-[5-(2-methoxyethoxy)pyridin-3-yl]-1,4-diazepane Chemical compound COCCOC1=CN=CC(N2CCNCCC2)=C1 SIPSUTQRUBWRRD-UHFFFAOYSA-N 0.000 claims description 2
- BIVCEXLTKFTSNE-UHFFFAOYSA-N 1-[5-(2-methylpropoxy)pyridin-3-yl]-1,4-diazepane Chemical compound CC(C)COC1=CN=CC(N2CCNCCC2)=C1 BIVCEXLTKFTSNE-UHFFFAOYSA-N 0.000 claims description 2
- RSRCMOHGADYDIP-UHFFFAOYSA-N 1-[5-(3-methylbutoxy)pyridin-3-yl]-1,4-diazepane Chemical compound CC(C)CCOC1=CN=CC(N2CCNCCC2)=C1 RSRCMOHGADYDIP-UHFFFAOYSA-N 0.000 claims description 2
- WMLBSRGFLMYCRL-UHFFFAOYSA-N 1-[5-(cyclohexylmethoxy)pyridin-3-yl]-1,4-diazepane Chemical compound C1CCCCC1COC(C=1)=CN=CC=1N1CCCNCC1 WMLBSRGFLMYCRL-UHFFFAOYSA-N 0.000 claims description 2
- BQKVPHLADFCQMM-UHFFFAOYSA-N 1-[5-(cyclohexylmethoxy)pyridin-3-yl]-4-methyl-1,4-diazepane Chemical compound C1CN(C)CCCN1C1=CN=CC(OCC2CCCCC2)=C1 BQKVPHLADFCQMM-UHFFFAOYSA-N 0.000 claims description 2
- XFKDCCSPHQFITP-UHFFFAOYSA-N 1-[5-(cyclopropylmethoxy)pyridin-3-yl]-4-methyl-1,4-diazepane Chemical compound C1CN(C)CCCN1C1=CN=CC(OCC2CC2)=C1 XFKDCCSPHQFITP-UHFFFAOYSA-N 0.000 claims description 2
- XSZHQYYEDXHKHO-UHFFFAOYSA-N 1-[5-(trifluoromethyl)pyridin-3-yl]-1,4-diazepane Chemical compound FC(F)(F)C1=CN=CC(N2CCNCCC2)=C1 XSZHQYYEDXHKHO-UHFFFAOYSA-N 0.000 claims description 2
- OJLZKNXSWYJFRQ-UHFFFAOYSA-N 1-ethyl-4-pyridin-3-yl-1,4-diazepane Chemical compound C1CN(CC)CCCN1C1=CC=CN=C1 OJLZKNXSWYJFRQ-UHFFFAOYSA-N 0.000 claims description 2
- UDFVXUBKLPYRRD-UHFFFAOYSA-N 1-fluoro-2-(2,2,2-triethoxyethyl)benzene Chemical compound CCOC(OCC)(OCC)CC1=CC=CC=C1F UDFVXUBKLPYRRD-UHFFFAOYSA-N 0.000 claims description 2
- HFMKRTPPJIJBMB-UHFFFAOYSA-N 1-methyl-4-(5-pentoxypyridin-3-yl)-1,4-diazepane Chemical compound CCCCCOC1=CN=CC(N2CCN(C)CCC2)=C1 HFMKRTPPJIJBMB-UHFFFAOYSA-N 0.000 claims description 2
- HFWNOGNDQAQFAK-UHFFFAOYSA-N 1-methyl-4-(5-phenylpyridin-3-yl)-1,4-diazepane Chemical compound C1CN(C)CCCN1C1=CN=CC(C=2C=CC=CC=2)=C1 HFWNOGNDQAQFAK-UHFFFAOYSA-N 0.000 claims description 2
- DVBACKKGNSUCLN-UHFFFAOYSA-N 1-methyl-4-(5-propoxypyridin-3-yl)-1,4-diazepane Chemical compound CCCOC1=CN=CC(N2CCN(C)CCC2)=C1 DVBACKKGNSUCLN-UHFFFAOYSA-N 0.000 claims description 2
- BEGXCDWYKVRXNN-UHFFFAOYSA-N 1-methyl-4-(5-pyridin-3-ylpyridin-3-yl)-1,4-diazepane Chemical compound C1CN(C)CCCN1C1=CN=CC(C=2C=NC=CC=2)=C1 BEGXCDWYKVRXNN-UHFFFAOYSA-N 0.000 claims description 2
- KARFYOZXIRIRRU-UHFFFAOYSA-N 1-methyl-4-[5-(3-methylbutoxy)pyridin-3-yl]-1,4-diazepane Chemical compound CC(C)CCOC1=CN=CC(N2CCN(C)CCC2)=C1 KARFYOZXIRIRRU-UHFFFAOYSA-N 0.000 claims description 2
- RAOIDXGYKMOZET-UHFFFAOYSA-N 3-(1,4-diazepan-1-yl)aniline Chemical compound NC1=CC=CC(N2CCNCCC2)=C1 RAOIDXGYKMOZET-UHFFFAOYSA-N 0.000 claims description 2
- FJCDUDLEMKEZCV-UHFFFAOYSA-N 3-(1,4-diazepan-1-yl)phenol Chemical compound OC1=CC=CC(N2CCNCCC2)=C1 FJCDUDLEMKEZCV-UHFFFAOYSA-N 0.000 claims description 2
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical group NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims description 2
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 2
- MJRZXRNJFQLHHY-UHFFFAOYSA-N 5-(1,4-diazepan-1-yl)pyridin-3-ol Chemical compound OC1=CN=CC(N2CCNCCC2)=C1 MJRZXRNJFQLHHY-UHFFFAOYSA-N 0.000 claims description 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 2
- FBXRDDHNMGDOCS-UHFFFAOYSA-N [5-(1,4-diazepan-1-yl)pyridin-3-yl] trifluoromethanesulfonate Chemical compound FC(F)(F)S(=O)(=O)OC1=CN=CC(N2CCNCCC2)=C1 FBXRDDHNMGDOCS-UHFFFAOYSA-N 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims description 2
- 208000013403 hyperactivity Diseases 0.000 claims description 2
- 125000001041 indolyl group Chemical group 0.000 claims description 2
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000004193 piperazinyl group Chemical group 0.000 claims description 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
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- 125000000168 pyrrolyl group Chemical group 0.000 claims description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 2
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- 125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 claims description 2
- TWDIXIZPEUQSNX-UHFFFAOYSA-N 1-(5-pyrrol-1-ylpyridin-3-yl)-1,4-diazepane Chemical compound C1CCNCCN1C1=CN=CC(N2C=CC=C2)=C1 TWDIXIZPEUQSNX-UHFFFAOYSA-N 0.000 claims 1
- DWSSUUAGRXYTAJ-UHFFFAOYSA-N 1-methyl-4-[5-(2-methylpropoxy)pyridin-3-yl]-1,4-diazepane Chemical compound CC(C)COC1=CN=CC(N2CCN(C)CCC2)=C1 DWSSUUAGRXYTAJ-UHFFFAOYSA-N 0.000 claims 1
- KZISNXPRKLLSJW-UHFFFAOYSA-N 4-(1,4-diazepan-1-yl)isoquinoline Chemical compound C1CCNCCN1C1=CN=CC2=CC=CC=C12 KZISNXPRKLLSJW-UHFFFAOYSA-N 0.000 claims 1
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- JISFKKNTDUCTTC-UHFFFAOYSA-N tert-butyl 4-[5-(3-nitrophenyl)pyridin-3-yl]-1,4-diazepane-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCCN1C1=CN=CC(C=2C=C(C=CC=2)[N+]([O-])=O)=C1 JISFKKNTDUCTTC-UHFFFAOYSA-N 0.000 description 1
- ZIPDKTKPNANWES-UHFFFAOYSA-N tert-butyl 4-quinolin-3-yl-1,4-diazepane-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCCN1C1=CN=C(C=CC=C2)C2=C1 ZIPDKTKPNANWES-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 208000005057 thyrotoxicosis Diseases 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- GTZCVFVGUGFEME-UHFFFAOYSA-N trans-aconitic acid Natural products OC(=O)CC(C(O)=O)=CC(O)=O GTZCVFVGUGFEME-UHFFFAOYSA-N 0.000 description 1
- 230000000472 traumatic effect Effects 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 208000037820 vascular cognitive impairment Diseases 0.000 description 1
- 239000002435 venom Substances 0.000 description 1
- 231100000611 venom Toxicity 0.000 description 1
- 210000001048 venom Anatomy 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000011345 viscous material Substances 0.000 description 1
- 230000002747 voluntary effect Effects 0.000 description 1
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Classifications
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- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/22—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing two or more pyridine rings directly linked together, e.g. bipyridyl
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/38—Nitrogen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
- C07D243/08—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 not condensed with other rings
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- 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
- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
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- 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
- C07D401/14—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 three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- 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
- C07D403/04—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 directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero 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
- C07D417/04—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 directly linked by a ring-member-to-ring-member bond
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- 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
- C07D417/14—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 three or more hetero rings
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Neurology (AREA)
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- Neurosurgery (AREA)
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- Psychiatry (AREA)
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- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Hospice & Palliative Care (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
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DK122597 | 1997-10-27 | ||
DK40998 | 1998-03-24 | ||
DK79698 | 1998-06-19 | ||
PCT/DK1998/000465 WO1999021834A1 (en) | 1997-10-27 | 1998-10-27 | Heteroaryl diazacycloalkanes as cholinergic ligands at nicotinic acetylcholine receptors |
Publications (3)
Publication Number | Publication Date |
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NO20002132D0 NO20002132D0 (no) | 2000-04-26 |
NO20002132L NO20002132L (no) | 2000-04-26 |
NO317094B1 true NO317094B1 (no) | 2004-08-09 |
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NO20002132A NO317094B1 (no) | 1997-10-27 | 2000-04-26 | Heteroaryldiazasykloalkaner som kolinerge ligander i nikotinsyreacetylkolinreseptorer |
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US (2) | US6825189B1 (cs) |
EP (2) | EP1491532B1 (cs) |
JP (1) | JP4570773B2 (cs) |
KR (1) | KR100607838B1 (cs) |
CN (1) | CN1131211C (cs) |
AT (2) | ATE278670T1 (cs) |
AU (1) | AU744539B2 (cs) |
BR (1) | BR9813279B1 (cs) |
CA (1) | CA2306093C (cs) |
CZ (1) | CZ299499B6 (cs) |
DE (2) | DE69826883T2 (cs) |
DK (1) | DK1027336T3 (cs) |
EE (1) | EE04588B1 (cs) |
ES (1) | ES2230723T3 (cs) |
HU (1) | HU226859B1 (cs) |
IL (2) | IL135108A0 (cs) |
IS (1) | IS5420A (cs) |
NO (1) | NO317094B1 (cs) |
NZ (1) | NZ503520A (cs) |
PL (1) | PL203140B1 (cs) |
PT (1) | PT1027336E (cs) |
RU (1) | RU2205179C2 (cs) |
SK (1) | SK285198B6 (cs) |
TR (1) | TR200001171T2 (cs) |
WO (1) | WO1999021834A1 (cs) |
Families Citing this family (65)
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US7214686B2 (en) | 1997-06-30 | 2007-05-08 | Targacept, Inc. | Pharmaceutical compositions and methods for effecting dopamine release |
CZ299499B6 (cs) * | 1997-10-27 | 2008-08-13 | Neurosearch A/S | Homopiperazinový derivát, farmaceutická kompoziceho obsahující a jeho použití |
AU773830B2 (en) * | 1999-04-26 | 2004-06-10 | Neurosearch A/S | Heteroaryl diazacycloalkanes, their preparation and use |
DE60008866T2 (de) | 1999-05-04 | 2005-01-27 | Neurosearch A/S | Heteroaryl diazabicycloalkene, deren herstellung und verwendung |
GB9914026D0 (en) * | 1999-06-17 | 1999-08-18 | Zeneca Ltd | Chemical compounds |
ATE289607T1 (de) | 1999-12-14 | 2005-03-15 | Neurosearch As | Neue heteroaryl-diazabizykloalkane |
MY145722A (en) * | 2000-04-27 | 2012-03-30 | Abbott Lab | Diazabicyclic central nervous system active agents |
US6809105B2 (en) | 2000-04-27 | 2004-10-26 | Abbott Laboratories | Diazabicyclic central nervous system active agents |
PT1358177E (pt) * | 2000-10-13 | 2006-09-29 | Neurosearch As | Tratamento de desordens afectivas atraves da accao combinada de um agonista do receptor nicotinico e uma substancia manoaminergica |
CA2341952A1 (en) | 2001-03-23 | 2002-09-23 | Universite Laval | Nicotinic receptor agonists for the treatment of inflammatory pulmonary diseases |
US8039459B2 (en) | 2004-07-15 | 2011-10-18 | Universite Laval | Nicotinic receptor agonists for the treatment of inflammatory diseases |
US8557804B2 (en) | 2002-03-25 | 2013-10-15 | Universite Laval | Nicotinic receptor agonists for the treatment of inflammatory diseases |
BR0312414A (pt) | 2002-07-05 | 2005-05-10 | Targacept Inc | Compostos de n-aril diazaespirociclico e métodos para a preparação e uso dos mesmos |
AU2003254016A1 (en) | 2002-07-19 | 2004-02-09 | Catholic Healthcare West | Methods and compositions relating to chimeric nicotinic receptor subunits |
US7098331B2 (en) | 2003-03-05 | 2006-08-29 | Targacept, Inc. | Arylvinylazacycloalkane compounds and methods of preparation and use thereof |
GB0316915D0 (en) | 2003-07-18 | 2003-08-20 | Glaxo Group Ltd | Compounds |
ATE451368T1 (de) | 2003-10-15 | 2009-12-15 | Targacept Inc | Azabicyclische verbindungen zur linderung von schmerzen und zur behandlung von erkrankungen des zentralen nervensystems |
WO2006031856A2 (en) | 2004-09-13 | 2006-03-23 | Chrono Therapeutics, Inc. | Biosynchronous transdermal drug delivery |
WO2006034338A1 (en) | 2004-09-20 | 2006-03-30 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as mediators of stearoyl-coa desaturase |
AU2005286793A1 (en) | 2004-09-20 | 2006-03-30 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives for the treatment of diseases mediated by stearoyl-CoA desaturase enzymes |
AR051202A1 (es) | 2004-09-20 | 2006-12-27 | Xenon Pharmaceuticals Inc | Derivados heterociclicos y su uso como inhibidores de la estearoil-coa desaturasa |
CN101084211A (zh) | 2004-09-20 | 2007-12-05 | 泽农医药公司 | 杂环衍生物及其作为治疗剂的用途 |
EP2269610A3 (en) | 2004-09-20 | 2011-03-09 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as stearoyl-coa desaturase inhibitors |
EP2266569A3 (en) | 2004-09-20 | 2011-03-09 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as stearoyl-coa desaturase inhibitors |
CN101044134A (zh) | 2004-09-20 | 2007-09-26 | 塔加西普特公司 | 具有烟碱性胆碱能受体活性的氮杂螺烯和氮杂螺烷化合物 |
BRPI0515499A (pt) * | 2004-09-20 | 2008-07-29 | Xenon Pharmaceuticals Inc | derivados de piridina para a inibição de estearoil-coa-desaturase humana |
US7829712B2 (en) | 2004-09-20 | 2010-11-09 | Xenon Pharmaceuticals Inc. | Pyridazine derivatives for inhibiting human stearoyl-CoA-desaturase |
UA88792C2 (ru) | 2004-11-10 | 2009-11-25 | Таргасепт, Інк. | Гидроксибензоатные соли метаникотиновых соединений |
US7459469B2 (en) | 2004-11-10 | 2008-12-02 | Targacept, Inc. | Hydroxybenzoate salts of metanicotine compounds |
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FR2885616B1 (fr) * | 2005-05-12 | 2007-06-22 | Servier Lab | Nouveaux derives de phenylpyridinylpiperazine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
FR2885615B1 (fr) * | 2005-05-12 | 2007-06-22 | Servier Lab | Nouveaux derives de phenylpyridinylpiperazine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
JP2009513563A (ja) | 2005-06-03 | 2009-04-02 | 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 | ヒトのステアロイル−CoAデサチュラーゼ阻害剤としてのアミノチアゾール誘導体 |
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