KR20080067339A - 1ｈ-인다졸, 벤조티아졸, 1,2-벤조이속사졸,1,2-벤조이소티아졸, 및 크로몬 및 그들의 제조법 및 용도 - Google Patents
1ｈ-인다졸, 벤조티아졸, 1,2-벤조이속사졸,1,2-벤조이소티아졸, 및 크로몬 및 그들의 제조법 및 용도 Download PDFInfo
- Publication number
- KR20080067339A KR20080067339A KR1020087011073A KR20087011073A KR20080067339A KR 20080067339 A KR20080067339 A KR 20080067339A KR 1020087011073 A KR1020087011073 A KR 1020087011073A KR 20087011073 A KR20087011073 A KR 20087011073A KR 20080067339 A KR20080067339 A KR 20080067339A
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- KR
- South Korea
- Prior art keywords
- carbon atoms
- diazabicyclo
- ylcarbonyl
- substituted
- alkyl
- 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.)
- Ceased
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- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 title abstract 3
- 238000002360 preparation method Methods 0.000 title description 21
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 title description 5
- CSNIZNHTOVFARY-UHFFFAOYSA-N 1,2-benzothiazole Chemical compound C1=CC=C2C=NSC2=C1 CSNIZNHTOVFARY-UHFFFAOYSA-N 0.000 title 1
- KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical compound C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 title 1
- OTAFHZMPRISVEM-UHFFFAOYSA-N chromone Chemical compound C1=CC=C2C(=O)C=COC2=C1 OTAFHZMPRISVEM-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 197
- 238000000034 method Methods 0.000 claims abstract description 190
- 239000000203 mixture Substances 0.000 claims abstract description 59
- 102000019315 Nicotinic acetylcholine receptors Human genes 0.000 claims abstract description 42
- 108050006807 Nicotinic acetylcholine receptors Proteins 0.000 claims abstract description 42
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 35
- 201000010099 disease Diseases 0.000 claims abstract description 26
- 230000004913 activation Effects 0.000 claims abstract description 9
- 230000002950 deficient Effects 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 242
- 229910005965 SO 2 Inorganic materials 0.000 claims description 138
- 125000000217 alkyl group Chemical group 0.000 claims description 131
- -1 NR 13 Inorganic materials 0.000 claims description 126
- 229910052801 chlorine Inorganic materials 0.000 claims description 110
- 229910052731 fluorine Inorganic materials 0.000 claims description 110
- 229910052794 bromium Inorganic materials 0.000 claims description 97
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 88
- 229910052740 iodine Inorganic materials 0.000 claims description 84
- 229910052736 halogen Inorganic materials 0.000 claims description 48
- 150000002367 halogens Chemical class 0.000 claims description 48
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 45
- 150000003839 salts Chemical class 0.000 claims description 41
- 125000003545 alkoxy group Chemical group 0.000 claims description 38
- 102000005962 receptors Human genes 0.000 claims description 34
- 108020003175 receptors Proteins 0.000 claims description 34
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 33
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 32
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 30
- 239000012458 free base Substances 0.000 claims description 25
- 125000004043 oxo group Chemical group O=* 0.000 claims description 25
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 24
- 125000000623 heterocyclic group Chemical group 0.000 claims description 23
- 206010012289 Dementia Diseases 0.000 claims description 22
- 229920006395 saturated elastomer Polymers 0.000 claims description 22
- 229910052799 carbon Inorganic materials 0.000 claims description 21
- 125000003118 aryl group Chemical group 0.000 claims description 20
- 208000010877 cognitive disease Diseases 0.000 claims description 19
- 206010027175 memory impairment Diseases 0.000 claims description 16
- 239000012453 solvate Substances 0.000 claims description 15
- 208000000044 Amnesia Diseases 0.000 claims description 14
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 13
- 229910052760 oxygen Inorganic materials 0.000 claims description 13
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 13
- 208000028698 Cognitive impairment Diseases 0.000 claims description 12
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims description 12
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 12
- 208000026139 Memory disease Diseases 0.000 claims description 11
- 150000001721 carbon Chemical group 0.000 claims description 11
- 125000002632 imidazolidinyl group Chemical group 0.000 claims description 11
- 230000006984 memory degeneration Effects 0.000 claims description 11
- 208000023060 memory loss Diseases 0.000 claims description 11
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 11
- 229910052717 sulfur Inorganic materials 0.000 claims description 11
- 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 description 10
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 208000024827 Alzheimer disease Diseases 0.000 claims description 9
- 241001465754 Metazoa Species 0.000 claims description 9
- 125000005959 diazepanyl group Chemical group 0.000 claims description 9
- 125000006413 ring segment Chemical group 0.000 claims description 9
- 150000001204 N-oxides Chemical class 0.000 claims description 8
- 125000004429 atom Chemical group 0.000 claims description 8
- 230000027455 binding Effects 0.000 claims description 8
- 230000001713 cholinergic effect Effects 0.000 claims description 8
- 230000000694 effects Effects 0.000 claims description 8
- 125000002757 morpholinyl group Chemical group 0.000 claims description 8
- 125000004193 piperazinyl group Chemical group 0.000 claims description 8
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- 206010012601 diabetes mellitus Diseases 0.000 claims description 7
- 208000035475 disorder Diseases 0.000 claims description 7
- 230000004064 dysfunction Effects 0.000 claims description 7
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- 201000000980 schizophrenia Diseases 0.000 claims description 7
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 7
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims description 6
- NASKHXNSXLBWOS-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(6-fluoro-2h-pyrazolo[3,4-b]pyridin-3-yl)methanone Chemical compound N=1NC2=NC(F)=CC=C2C=1C(=O)N1CCN2CCC1CC2 NASKHXNSXLBWOS-UHFFFAOYSA-N 0.000 claims description 6
- CDQFTKBQYMHUKI-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(6-morpholin-4-yl-1h-indazol-3-yl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C1=CC=2)=NNC1=CC=2N1CCOCC1 CDQFTKBQYMHUKI-UHFFFAOYSA-N 0.000 claims description 6
- PGHTXZVHWVYKII-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(6-pyrrolidin-1-yl-1h-indazol-3-yl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C1=CC=2)=NNC1=CC=2N1CCCC1 PGHTXZVHWVYKII-UHFFFAOYSA-N 0.000 claims description 6
- XDLAJOHFJBFDBR-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(6-thiomorpholin-4-yl-1h-indazol-3-yl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C1=CC=2)=NNC1=CC=2N1CCSCC1 XDLAJOHFJBFDBR-UHFFFAOYSA-N 0.000 claims description 6
- YANZINWIXKAPBJ-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-[6-(1,4-oxazepan-4-yl)-1h-indazol-3-yl]methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C1=CC=2)=NNC1=CC=2N1CCCOCC1 YANZINWIXKAPBJ-UHFFFAOYSA-N 0.000 claims description 6
- SDGFKGORCOJBTQ-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-[6-(3-methoxypyrrolidin-1-yl)-1h-indazol-3-yl]methanone Chemical compound C1C(OC)CCN1C1=CC=C(C(=NN2)C(=O)N3C4CCN(CC4)CC3)C2=C1 SDGFKGORCOJBTQ-UHFFFAOYSA-N 0.000 claims description 6
- BDJQBBPBWIKLPI-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-[6-(4-methyl-1,4-diazepan-1-yl)-1h-indazol-3-yl]methanone Chemical compound C1CN(C)CCCN1C1=CC=C(C(=NN2)C(=O)N3C4CCN(CC4)CC3)C2=C1 BDJQBBPBWIKLPI-UHFFFAOYSA-N 0.000 claims description 6
- CZUBGJIEWJEYLG-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-[6-(4-methylpiperazin-1-yl)-1h-indazol-3-yl]methanone Chemical compound C1CN(C)CCN1C1=CC=C(C(=NN2)C(=O)N3C4CCN(CC4)CC3)C2=C1 CZUBGJIEWJEYLG-UHFFFAOYSA-N 0.000 claims description 6
- KGLWXAZNCVRDSK-UHFFFAOYSA-N 1-[3-(1,4-diazabicyclo[3.2.2]nonane-4-carbonyl)-1h-indazol-6-yl]-3-propylimidazolidin-2-one Chemical compound O=C1N(CCC)CCN1C1=CC=C(C(=NN2)C(=O)N3C4CCN(CC4)CC3)C2=C1 KGLWXAZNCVRDSK-UHFFFAOYSA-N 0.000 claims description 6
- 208000023105 Huntington disease Diseases 0.000 claims description 6
- 201000004810 Vascular dementia Diseases 0.000 claims description 6
- 230000032683 aging Effects 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 6
- 230000006735 deficit Effects 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 6
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 6
- 230000015654 memory Effects 0.000 claims description 6
- 210000002569 neuron Anatomy 0.000 claims description 6
- 229960002715 nicotine Drugs 0.000 claims description 6
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 claims description 6
- 208000011580 syndromic disease Diseases 0.000 claims description 6
- LTTRHAHKHBGLFJ-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(5-methoxy-1,2-benzothiazol-3-yl)methanone Chemical compound C12=CC(OC)=CC=C2SN=C1C(=O)N1CCN2CCC1CC2 LTTRHAHKHBGLFJ-UHFFFAOYSA-N 0.000 claims description 5
- 125000004423 acyloxy group Chemical group 0.000 claims description 5
- 230000007000 age related cognitive decline Effects 0.000 claims description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 5
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 5
- 125000004414 alkyl thio group Chemical group 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 230000007812 deficiency Effects 0.000 claims description 5
- 125000005113 hydroxyalkoxy group Chemical group 0.000 claims description 5
- 208000027866 inflammatory disease Diseases 0.000 claims description 5
- 208000027061 mild cognitive impairment Diseases 0.000 claims description 5
- 230000000638 stimulation Effects 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- FOPHMSZZCWXLSE-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(6-pyrrolidin-1-yl-1,2-benzothiazol-3-yl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C1=CC=2)=NSC1=CC=2N1CCCC1 FOPHMSZZCWXLSE-UHFFFAOYSA-N 0.000 claims description 4
- IVDYMQJQBOZDLZ-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-[5-(oxan-3-yloxy)-1h-indazol-3-yl]methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C1=C2)=NNC1=CC=C2OC1CCCOC1 IVDYMQJQBOZDLZ-UHFFFAOYSA-N 0.000 claims description 4
- AMKLHPFMAYQUSV-MRXNPFEDSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-[5-[(3r)-3-methoxypyrrolidin-1-yl]-1h-indazol-3-yl]methanone Chemical compound C1[C@H](OC)CCN1C1=CC=C(NN=C2C(=O)N3C4CCN(CC4)CC3)C2=C1 AMKLHPFMAYQUSV-MRXNPFEDSA-N 0.000 claims description 4
- AMKLHPFMAYQUSV-INIZCTEOSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-[5-[(3s)-3-methoxypyrrolidin-1-yl]-1h-indazol-3-yl]methanone Chemical compound C1[C@@H](OC)CCN1C1=CC=C(NN=C2C(=O)N3C4CCN(CC4)CC3)C2=C1 AMKLHPFMAYQUSV-INIZCTEOSA-N 0.000 claims description 4
- VKKAITWTUBGNFK-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-[5-[4-(2,2,2-trifluoroethyl)-1,4-diazepan-1-yl]-1h-indazol-3-yl]methanone Chemical compound C1CN(CC(F)(F)F)CCCN1C1=CC=C(NN=C2C(=O)N3C4CCN(CC4)CC3)C2=C1 VKKAITWTUBGNFK-UHFFFAOYSA-N 0.000 claims description 4
- UNMAWYMYPJVFBB-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-[6-(1,4-diazabicyclo[3.2.2]nonan-4-yl)-1,2-benzothiazol-3-yl]methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C1=CC=2)=NSC1=CC=2N1CCN2CCC1CC2 UNMAWYMYPJVFBB-UHFFFAOYSA-N 0.000 claims description 4
- MODJKVLWMQXWNQ-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-[6-(1-methylpyrrolidin-3-yl)oxy-1,2-benzothiazol-3-yl]methanone Chemical compound C1N(C)CCC1OC1=CC=C(C(=NS2)C(=O)N3C4CCN(CC4)CC3)C2=C1 MODJKVLWMQXWNQ-UHFFFAOYSA-N 0.000 claims description 4
- OTCDNWYAYRJYFI-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-[6-(4-methylpiperazin-1-yl)-1,2-benzothiazol-3-yl]methanone Chemical compound C1CN(C)CCN1C1=CC=C(C(=NS2)C(=O)N3C4CCN(CC4)CC3)C2=C1 OTCDNWYAYRJYFI-UHFFFAOYSA-N 0.000 claims description 4
- OPBMDLXCLRKRON-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-[6-(5-methyl-2,5-diazabicyclo[2.2.2]octan-2-yl)-1,2-benzothiazol-3-yl]methanone Chemical compound CN1CC2CCC1CN2C(C=C1SN=2)=CC=C1C=2C(=O)N1CCN2CCC1CC2 OPBMDLXCLRKRON-UHFFFAOYSA-N 0.000 claims description 4
- BHNLNIXBMVMWBJ-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-[6-(oxan-3-yloxy)-1h-indazol-3-yl]methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C1=CC=2)=NNC1=CC=2OC1CCCOC1 BHNLNIXBMVMWBJ-UHFFFAOYSA-N 0.000 claims description 4
- UKVXPHCQATZHCH-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-[6-(oxan-4-yloxy)-1h-indazol-3-yl]methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C1=CC=2)=NNC1=CC=2OC1CCOCC1 UKVXPHCQATZHCH-UHFFFAOYSA-N 0.000 claims description 4
- YYMONJYIJHVWEZ-IAGOWNOFSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-[6-[(1r,4r)-5-methyl-2,5-diazabicyclo[2.2.1]heptan-2-yl]-1,2-benzothiazol-3-yl]methanone Chemical compound C([C@@]1(N(C[C@@]2([H])C1)C)[H])N2C(C=C1SN=2)=CC=C1C=2C(=O)N1CCN2CCC1CC2 YYMONJYIJHVWEZ-IAGOWNOFSA-N 0.000 claims description 4
- YYMONJYIJHVWEZ-IRXDYDNUSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-[6-[(1s,4s)-5-methyl-2,5-diazabicyclo[2.2.1]heptan-2-yl]-1,2-benzothiazol-3-yl]methanone Chemical compound C([C@]1(N(C[C@]2([H])C1)C)[H])N2C(C=C1SN=2)=CC=C1C=2C(=O)N1CCN2CCC1CC2 YYMONJYIJHVWEZ-IRXDYDNUSA-N 0.000 claims description 4
- SDGFKGORCOJBTQ-MRXNPFEDSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-[6-[(3r)-3-methoxypyrrolidin-1-yl]-1h-indazol-3-yl]methanone Chemical compound C1[C@H](OC)CCN1C1=CC=C(C(=NN2)C(=O)N3C4CCN(CC4)CC3)C2=C1 SDGFKGORCOJBTQ-MRXNPFEDSA-N 0.000 claims description 4
- SDGFKGORCOJBTQ-INIZCTEOSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-[6-[(3s)-3-methoxypyrrolidin-1-yl]-1h-indazol-3-yl]methanone Chemical compound C1[C@@H](OC)CCN1C1=CC=C(C(=NN2)C(=O)N3C4CCN(CC4)CC3)C2=C1 SDGFKGORCOJBTQ-INIZCTEOSA-N 0.000 claims description 4
- KYDAVMPYAGTHOG-UHFFFAOYSA-N 1-[3-(1,4-diazabicyclo[3.2.2]nonane-4-carbonyl)-1-methylindazol-6-yl]-3-propylurea Chemical compound N=1N(C)C2=CC(NC(=O)NCCC)=CC=C2C=1C(=O)N1CCN2CCC1CC2 KYDAVMPYAGTHOG-UHFFFAOYSA-N 0.000 claims description 4
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
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- 206010044221 Toxic encephalopathy Diseases 0.000 claims description 4
- GNPCXQKUXPFHNC-UHFFFAOYSA-N [6-(1-azabicyclo[2.2.2]octan-3-yloxy)-1,2-benzothiazol-3-yl]-(1,4-diazabicyclo[3.2.2]nonan-4-yl)methanone Chemical compound N=1SC2=CC(OC3C4CCN(CC4)C3)=CC=C2C=1C(=O)N1CCN2CCC1CC2 GNPCXQKUXPFHNC-UHFFFAOYSA-N 0.000 claims description 4
- HPELPVSEHNCJLX-UHFFFAOYSA-N [6-(3,4,6,7,8,8a-hexahydro-1h-pyrrolo[1,2-a]pyrazin-2-yl)-1,2-benzothiazol-3-yl]-(1,4-diazabicyclo[3.2.2]nonan-4-yl)methanone Chemical compound N=1SC2=CC(N3CC4CCCN4CC3)=CC=C2C=1C(=O)N1CCN2CCC1CC2 HPELPVSEHNCJLX-UHFFFAOYSA-N 0.000 claims description 4
- DOGJICDABWIVPC-BBRMVZONSA-N [6-[(1s,4s)-2,5-diazabicyclo[2.2.1]heptan-2-yl]-1,2-benzothiazol-3-yl]-(1,4-diazabicyclo[3.2.2]nonan-4-yl)methanone Chemical compound C([C@]1(NC[C@]2([H])C1)[H])N2C(C=C1SN=2)=CC=C1C=2C(=O)N1CCN2CCC1CC2 DOGJICDABWIVPC-BBRMVZONSA-N 0.000 claims description 4
- OXDKBEYNLGGKKV-PMACEKPBSA-N [6-[(1s,4s)-5-(cyclopropylmethyl)-2,5-diazabicyclo[2.2.1]heptan-2-yl]-1,2-benzothiazol-3-yl]-(1,4-diazabicyclo[3.2.2]nonan-4-yl)methanone Chemical compound C([C@]1(N(C=2C=C3SN=C(C3=CC=2)C(=O)N2C3CCN(CC3)CC2)C[C@@]2(C1)[H])[H])N2CC1CC1 OXDKBEYNLGGKKV-PMACEKPBSA-N 0.000 claims description 4
- AZIYSLGXZWNCRO-OALUTQOASA-N [6-[(1s,4s)-5-cyclopropyl-2,5-diazabicyclo[2.2.1]heptan-2-yl]-1,2-benzothiazol-3-yl]-(1,4-diazabicyclo[3.2.2]nonan-4-yl)methanone Chemical compound C([C@]1(N(C=2C=C3SN=C(C3=CC=2)C(=O)N2C3CCN(CC3)CC2)C[C@@]2(C1)[H])[H])N2C1CC1 AZIYSLGXZWNCRO-OALUTQOASA-N 0.000 claims description 4
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 4
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 4
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 4
- 125000005110 aryl thio group Chemical group 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 4
- 229940079593 drug Drugs 0.000 claims description 4
- 230000004112 neuroprotection Effects 0.000 claims description 4
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- IAUJNRYBYIWAOJ-UHFFFAOYSA-N tert-butyl 6-(1-methyl-4,5-dihydroimidazol-2-yl)-1h-indazole-3-carboxylate Chemical compound CN1CCN=C1C1=CC=C(C(=NN2)C(=O)OC(C)(C)C)C2=C1 IAUJNRYBYIWAOJ-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
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- 238000011285 therapeutic regimen Methods 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- GZNAASVAJNXPPW-UHFFFAOYSA-M tin(4+) chloride dihydrate Chemical compound O.O.[Cl-].[Sn+4] GZNAASVAJNXPPW-UHFFFAOYSA-M 0.000 description 1
- FWPIDFUJEMBDLS-UHFFFAOYSA-L tin(II) chloride dihydrate Substances O.O.Cl[Sn]Cl FWPIDFUJEMBDLS-UHFFFAOYSA-L 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 231100000583 toxicological profile Toxicity 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
- 208000018726 traumatic encephalopathy Diseases 0.000 description 1
- 125000006250 trifluoro ethyl amino group Chemical group [H]N(*)C([H])([H])C(F)(F)F 0.000 description 1
- 208000032527 type III spinal muscular atrophy Diseases 0.000 description 1
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 1
- 125000005500 uronium group Chemical group 0.000 description 1
- 210000001186 vagus nerve Anatomy 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- CXNIUSPIQKWYAI-UHFFFAOYSA-N xantphos Chemical compound C=12OC3=C(P(C=4C=CC=CC=4)C=4C=CC=CC=4)C=CC=C3C(C)(C)C2=CC=CC=1P(C=1C=CC=CC=1)C1=CC=CC=C1 CXNIUSPIQKWYAI-UHFFFAOYSA-N 0.000 description 1
- LYTCVQQGCSNFJU-LKGYBJPKSA-N α-bungarotoxin Chemical compound C(/[C@H]1O[C@H]2C[C@H]3O[C@@H](CC(=C)C=O)C[C@H](O)[C@]3(C)O[C@@H]2C[C@@H]1O[C@@H]1C2)=C/C[C@]1(C)O[C@H]1[C@@]2(C)O[C@]2(C)CC[C@@H]3O[C@@H]4C[C@]5(C)O[C@@H]6C(C)=CC(=O)O[C@H]6C[C@H]5O[C@H]4C[C@@H](C)[C@H]3O[C@H]2C1 LYTCVQQGCSNFJU-LKGYBJPKSA-N 0.000 description 1
Classifications
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- 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
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- 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
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- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
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- Addiction (AREA)
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- Anesthesiology (AREA)
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- Hematology (AREA)
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- Emergency Medicine (AREA)
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- Communicable Diseases (AREA)
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- Endocrinology (AREA)
- Heart & Thoracic Surgery (AREA)
- Child & Adolescent Psychology (AREA)
- Oncology (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US73476105P | 2005-11-09 | 2005-11-09 | |
| US60/734,761 | 2005-11-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20080067339A true KR20080067339A (ko) | 2008-07-18 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020087011073A Ceased KR20080067339A (ko) | 2005-11-09 | 2006-11-09 | 1ｈ-인다졸, 벤조티아졸, 1,2-벤조이속사졸,1,2-벤조이소티아졸, 및 크로몬 및 그들의 제조법 및 용도 |
Country Status (10)
| Country | Link |
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| US (1) | US7932248B2 (enExample) |
| EP (1) | EP1963332A1 (enExample) |
| JP (1) | JP2009514980A (enExample) |
| KR (1) | KR20080067339A (enExample) |
| CN (1) | CN101316849A (enExample) |
| AU (1) | AU2006311422A1 (enExample) |
| BR (1) | BRPI0619672A2 (enExample) |
| CA (1) | CA2627089A1 (enExample) |
| IL (1) | IL190874A0 (enExample) |
| WO (1) | WO2007056582A1 (enExample) |
Families Citing this family (13)
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| 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 |
| PE20061119A1 (es) | 2005-01-19 | 2006-11-27 | Aventis Pharma Sa | PIRAZOLO PIRIDINAS SUSTITUIDAS COMO INHIBIDORES DE CINASAS FAK, KDR Y Tie |
| FR2889526B1 (fr) | 2005-08-04 | 2012-02-17 | Aventis Pharma Sa | 7-aza-indazoles substitues, compositions les contenant, procede de fabrication et utilisation |
| WO2009055437A2 (en) * | 2007-10-22 | 2009-04-30 | Memory Pharmaceuticals Corporation | (1,4-diaza-bicyclo[3.2.2]non-6-en-4-yl)-heterocyclyl-methanone ligands for nicotinic acetylcholine receptors, useful for the treatment of disease |
| JO3250B1 (ar) | 2009-09-22 | 2018-09-16 | Novartis Ag | إستعمال منشطات مستقبل نيكوتينيك أسيتيل كولين ألفا 7 |
| CU24152B1 (es) | 2010-12-20 | 2016-02-29 | Irm Llc | 1,2 oxazol-8-azabiciclo[3,2,1]octano 8 il como moduladores de fxr |
| EP2548870A1 (en) * | 2011-07-20 | 2013-01-23 | Cytec Technology Corp. | Process for the Synthesis of Cyclic Alkylene Ureas |
| EP2548869A1 (en) * | 2011-07-20 | 2013-01-23 | Cytec Technology Corp. | Process for the Synthesis of N-substituted Cyclic Alkylene Ureas |
| US8889730B2 (en) | 2012-04-10 | 2014-11-18 | Pfizer Inc. | Indole and indazole compounds that activate AMPK |
| US9394285B2 (en) | 2013-03-15 | 2016-07-19 | Pfizer Inc. | Indole and indazole compounds that activate AMPK |
| CN106279119B (zh) * | 2015-05-27 | 2020-06-16 | 上海海和药物研究开发有限公司 | 一种新型激酶抑制剂的制备及其应用 |
| CN110494136A (zh) * | 2017-01-10 | 2019-11-22 | 瑞士苏黎世联邦理工学院 | 细胞保护性化合物及其用途 |
| US20240051939A1 (en) * | 2020-12-08 | 2024-02-15 | Disarm Therapeutics, Inc. | Benzopyrazole inhibitors of sarm1 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
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| SE0202465D0 (sv) * | 2002-08-14 | 2002-08-14 | Astrazeneca Ab | New compounds |
| CA2499128C (en) * | 2002-09-25 | 2012-07-31 | Memory Pharmaceuticals Corporation | Indazoles, benzothiazoles, and benzoisothiazoles, and preparation and uses thereof |
| US7456171B2 (en) * | 2002-10-08 | 2008-11-25 | Sanofi-Aventis | 1,4-Diazabicyclo[3.2.2]nonanecarboxamide derivatives, preparation and therapeutic use thereof |
| FR2845388B1 (fr) * | 2002-10-08 | 2004-11-12 | Sanofi Synthelabo | Derives de 1,4-diazabicyclo[3.2.2]nonanecarboxamides, leur preparation et leur application en therapeutique |
| US7396833B2 (en) | 2003-12-22 | 2008-07-08 | Memory Pharmaceuticals Corporation | Indoles, 1H-indazoles, 1,2-benzisoxazoles, and 1,2-benzisothiazoles, and preparation and uses thereof |
| CN103724343A (zh) * | 2004-03-25 | 2014-04-16 | 记忆药物公司 | 吲唑、苯并噻唑、苯并异噻唑、苯并异噁唑及其制备和用途 |
-
2006
- 2006-11-09 CA CA002627089A patent/CA2627089A1/en not_active Abandoned
- 2006-11-09 JP JP2008540217A patent/JP2009514980A/ja active Pending
- 2006-11-09 BR BRPI0619672-1A patent/BRPI0619672A2/pt not_active IP Right Cessation
- 2006-11-09 US US11/594,993 patent/US7932248B2/en not_active Expired - Fee Related
- 2006-11-09 EP EP06837344A patent/EP1963332A1/en not_active Withdrawn
- 2006-11-09 KR KR1020087011073A patent/KR20080067339A/ko not_active Ceased
- 2006-11-09 AU AU2006311422A patent/AU2006311422A1/en not_active Abandoned
- 2006-11-09 WO PCT/US2006/043818 patent/WO2007056582A1/en not_active Ceased
- 2006-11-09 CN CNA2006800420321A patent/CN101316849A/zh active Pending
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2008
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Also Published As
| Publication number | Publication date |
|---|---|
| CA2627089A1 (en) | 2007-05-18 |
| WO2007056582A1 (en) | 2007-05-18 |
| IL190874A0 (en) | 2008-11-03 |
| AU2006311422A1 (en) | 2007-05-18 |
| CN101316849A (zh) | 2008-12-03 |
| JP2009514980A (ja) | 2009-04-09 |
| US7932248B2 (en) | 2011-04-26 |
| BRPI0619672A2 (pt) | 2011-10-11 |
| US20070135417A1 (en) | 2007-06-14 |
| EP1963332A1 (en) | 2008-09-03 |
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