CA2493920A1 - Biaryl diazabicycloalkane amides as nicotinic acetylcholine agonists - Google Patents
Biaryl diazabicycloalkane amides as nicotinic acetylcholine agonists Download PDFInfo
- Publication number
- CA2493920A1 CA2493920A1 CA002493920A CA2493920A CA2493920A1 CA 2493920 A1 CA2493920 A1 CA 2493920A1 CA 002493920 A CA002493920 A CA 002493920A CA 2493920 A CA2493920 A CA 2493920A CA 2493920 A1 CA2493920 A1 CA 2493920A1
- Authority
- CA
- Canada
- Prior art keywords
- methanone
- diazabicyclo
- furan
- thiophen
- pyridyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 150000001408 amides Chemical class 0.000 title description 14
- 125000005841 biaryl group Chemical group 0.000 title 1
- 239000000064 cholinergic agonist Substances 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract description 38
- 150000003839 salts Chemical class 0.000 claims abstract description 36
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 25
- 238000011282 treatment Methods 0.000 claims abstract description 22
- 102000019315 Nicotinic acetylcholine receptors Human genes 0.000 claims abstract description 18
- 108050006807 Nicotinic acetylcholine receptors Proteins 0.000 claims abstract description 18
- 230000006735 deficit Effects 0.000 claims abstract description 16
- 208000035475 disorder Diseases 0.000 claims abstract description 14
- 238000011321 prophylaxis Methods 0.000 claims abstract description 13
- 201000010099 disease Diseases 0.000 claims abstract description 9
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 7
- 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
- 208000019901 Anxiety disease Diseases 0.000 claims abstract description 6
- 208000002193 Pain Diseases 0.000 claims abstract description 6
- 230000036506 anxiety Effects 0.000 claims abstract description 6
- 201000000980 schizophrenia Diseases 0.000 claims abstract description 6
- 208000000044 Amnesia Diseases 0.000 claims abstract description 5
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims abstract description 5
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims abstract description 5
- 208000020925 Bipolar disease Diseases 0.000 claims abstract description 5
- 208000019888 Circadian rhythm sleep disease Diseases 0.000 claims abstract description 5
- 206010009900 Colitis ulcerative Diseases 0.000 claims abstract description 5
- 208000001456 Jet Lag Syndrome Diseases 0.000 claims abstract description 5
- 206010026749 Mania Diseases 0.000 claims abstract description 5
- 208000026139 Memory disease Diseases 0.000 claims abstract description 5
- 208000028017 Psychotic disease Diseases 0.000 claims abstract description 5
- 201000006704 Ulcerative Colitis Diseases 0.000 claims abstract description 5
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims abstract description 5
- 208000028683 bipolar I disease Diseases 0.000 claims abstract description 5
- 230000001713 cholinergic effect Effects 0.000 claims abstract description 5
- 230000007278 cognition impairment Effects 0.000 claims abstract description 5
- 208000033915 jet lag type circadian rhythm sleep disease Diseases 0.000 claims abstract description 5
- 230000006984 memory degeneration Effects 0.000 claims abstract description 5
- 208000023060 memory loss Diseases 0.000 claims abstract description 5
- 208000015122 neurodegenerative disease Diseases 0.000 claims abstract description 5
- 230000036407 pain Effects 0.000 claims abstract description 5
- 210000000225 synapse Anatomy 0.000 claims abstract description 5
- 208000009829 Lewy Body Disease Diseases 0.000 claims abstract description 4
- 201000002832 Lewy body dementia Diseases 0.000 claims abstract description 4
- 206010057852 Nicotine dependence Diseases 0.000 claims abstract description 4
- 208000025569 Tobacco Use disease Diseases 0.000 claims abstract description 4
- 230000003935 attention Effects 0.000 claims abstract description 4
- 208000002551 irritable bowel syndrome Diseases 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 180
- 229910052760 oxygen Inorganic materials 0.000 claims description 66
- 239000001301 oxygen Substances 0.000 claims description 64
- 239000002904 solvent Substances 0.000 claims description 64
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 63
- 229910052717 sulfur Inorganic materials 0.000 claims description 48
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 45
- 239000011593 sulfur Substances 0.000 claims description 45
- 229910052736 halogen Inorganic materials 0.000 claims description 42
- 150000002367 halogens Chemical class 0.000 claims description 42
- 239000003054 catalyst Substances 0.000 claims description 34
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 33
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 32
- 125000005842 heteroatom Chemical group 0.000 claims description 29
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 26
- 125000002524 organometallic group Chemical group 0.000 claims description 24
- 229910052757 nitrogen Inorganic materials 0.000 claims description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 17
- 125000001424 substituent group Chemical group 0.000 claims description 17
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
- GNPQLYUSJOCBMA-UHFFFAOYSA-N (5-bromofuran-2-yl)-(1,4-diazabicyclo[3.2.2]nonan-4-yl)methanone Chemical compound O1C(Br)=CC=C1C(=O)N1C(CC2)CCN2CC1 GNPQLYUSJOCBMA-UHFFFAOYSA-N 0.000 claims description 9
- 125000001072 heteroaryl group Chemical group 0.000 claims description 9
- 101100294106 Caenorhabditis elegans nhr-3 gene Proteins 0.000 claims description 8
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 8
- 229960002715 nicotine Drugs 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 6
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims description 5
- 208000024827 Alzheimer disease Diseases 0.000 claims description 5
- 208000018737 Parkinson disease Diseases 0.000 claims description 5
- 208000000323 Tourette Syndrome Diseases 0.000 claims description 5
- 208000016620 Tourette disease Diseases 0.000 claims description 5
- 150000002902 organometallic compounds Chemical class 0.000 claims description 5
- OGZLAVDBQCWTRH-UHFFFAOYSA-N (3-bromophenyl)-(1,4-diazabicyclo[3.2.2]nonan-4-yl)methanone Chemical compound BrC1=CC=CC(C(=O)N2C3CCN(CC3)CC2)=C1 OGZLAVDBQCWTRH-UHFFFAOYSA-N 0.000 claims description 4
- PFOHKMLFVACSFW-UHFFFAOYSA-N (5-bromothiophen-2-yl)-(1,4-diazabicyclo[3.2.2]nonan-4-yl)methanone Chemical compound S1C(Br)=CC=C1C(=O)N1C(CC2)CCN2CC1 PFOHKMLFVACSFW-UHFFFAOYSA-N 0.000 claims description 4
- LFQXLDRICKOWGM-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(3-thiophen-2-ylphenyl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C=1)=CC=CC=1C1=CC=CS1 LFQXLDRICKOWGM-UHFFFAOYSA-N 0.000 claims description 4
- 208000023105 Huntington disease Diseases 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 230000000391 smoking effect Effects 0.000 claims description 4
- IXKRDKNQHUOVKG-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(3-phenylphenyl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C=1)=CC=CC=1C1=CC=CC=C1 IXKRDKNQHUOVKG-UHFFFAOYSA-N 0.000 claims description 3
- SODJXZKVCLJFEE-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(5-phenylthiophen-2-yl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(S1)=CC=C1C1=CC=CC=C1 SODJXZKVCLJFEE-UHFFFAOYSA-N 0.000 claims description 3
- RLJRNTDELRCHII-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(5-pyridin-4-ylthiophen-3-yl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C=1)=CSC=1C1=CC=NC=C1 RLJRNTDELRCHII-UHFFFAOYSA-N 0.000 claims description 3
- 230000004913 activation Effects 0.000 claims description 3
- 230000009286 beneficial effect Effects 0.000 claims description 3
- CSIFTQTVMGTFIA-UHFFFAOYSA-N (4-bromophenyl)-(1,4-diazabicyclo[3.2.2]nonan-4-yl)methanone Chemical compound C1=CC(Br)=CC=C1C(=O)N1C(CC2)CCN2CC1 CSIFTQTVMGTFIA-UHFFFAOYSA-N 0.000 claims description 2
- PFARLMJTRBXTQP-UHFFFAOYSA-N (4-bromothiophen-2-yl)-(1,4-diazabicyclo[3.2.2]nonan-4-yl)methanone Chemical compound BrC1=CSC(C(=O)N2C3CCN(CC3)CC2)=C1 PFARLMJTRBXTQP-UHFFFAOYSA-N 0.000 claims description 2
- DNQWTTQUOXMVJD-UHFFFAOYSA-N (5-bromothiophen-3-yl)-(1,4-diazabicyclo[3.2.2]nonan-4-yl)methanone Chemical compound S1C(Br)=CC(C(=O)N2C3CCN(CC3)CC2)=C1 DNQWTTQUOXMVJD-UHFFFAOYSA-N 0.000 claims description 2
- UVZLCLJQMZJFJL-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(3-iodophenyl)methanone Chemical compound IC1=CC=CC(C(=O)N2C3CCN(CC3)CC2)=C1 UVZLCLJQMZJFJL-UHFFFAOYSA-N 0.000 claims description 2
- UCMQCNNZHLFWQP-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(3-pyridin-2-ylphenyl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C=1)=CC=CC=1C1=CC=CC=N1 UCMQCNNZHLFWQP-UHFFFAOYSA-N 0.000 claims description 2
- CDSCDKTXQWLABR-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(3-pyridin-3-ylphenyl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C=1)=CC=CC=1C1=CC=CN=C1 CDSCDKTXQWLABR-UHFFFAOYSA-N 0.000 claims description 2
- GENNWRVZHQPVBO-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(3-pyridin-4-ylphenyl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C=1)=CC=CC=1C1=CC=NC=C1 GENNWRVZHQPVBO-UHFFFAOYSA-N 0.000 claims description 2
- FUDFPUYWRXFOOH-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(3-thiophen-3-ylphenyl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C=1)=CC=CC=1C=1C=CSC=1 FUDFPUYWRXFOOH-UHFFFAOYSA-N 0.000 claims description 2
- HAXPXNGBJPFDGV-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(4-iodophenyl)methanone Chemical compound C1=CC(I)=CC=C1C(=O)N1C(CC2)CCN2CC1 HAXPXNGBJPFDGV-UHFFFAOYSA-N 0.000 claims description 2
- ITPFUCDKDQZSAY-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(4-phenylfuran-2-yl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(OC=1)=CC=1C1=CC=CC=C1 ITPFUCDKDQZSAY-UHFFFAOYSA-N 0.000 claims description 2
- WTSKNUGIAJZTMU-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(4-phenylphenyl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C=C1)=CC=C1C1=CC=CC=C1 WTSKNUGIAJZTMU-UHFFFAOYSA-N 0.000 claims description 2
- YFNUMKDCWUSIRV-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(4-phenylthiophen-2-yl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(SC=1)=CC=1C1=CC=CC=C1 YFNUMKDCWUSIRV-UHFFFAOYSA-N 0.000 claims description 2
- MZMRVHKSQCNPKT-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(4-pyridin-2-ylfuran-2-yl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(OC=1)=CC=1C1=CC=CC=N1 MZMRVHKSQCNPKT-UHFFFAOYSA-N 0.000 claims description 2
- RJJNRYMNCLCVOG-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(4-pyridin-2-ylphenyl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C=C1)=CC=C1C1=CC=CC=N1 RJJNRYMNCLCVOG-UHFFFAOYSA-N 0.000 claims description 2
- ZNVCOLOEINQRSA-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(4-pyridin-2-ylthiophen-2-yl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(SC=1)=CC=1C1=CC=CC=N1 ZNVCOLOEINQRSA-UHFFFAOYSA-N 0.000 claims description 2
- DHJJHUMTVYKNTK-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(4-pyridin-3-ylphenyl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C=C1)=CC=C1C1=CC=CN=C1 DHJJHUMTVYKNTK-UHFFFAOYSA-N 0.000 claims description 2
- IDJXUTJMHGLAQD-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(4-pyridin-4-ylfuran-2-yl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(OC=1)=CC=1C1=CC=NC=C1 IDJXUTJMHGLAQD-UHFFFAOYSA-N 0.000 claims description 2
- IRIRSSBNMMWXKV-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(4-pyridin-4-ylphenyl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C=C1)=CC=C1C1=CC=NC=C1 IRIRSSBNMMWXKV-UHFFFAOYSA-N 0.000 claims description 2
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- IQQWZDQMXJJYNM-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(4-thiophen-2-ylphenyl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C=C1)=CC=C1C1=CC=CS1 IQQWZDQMXJJYNM-UHFFFAOYSA-N 0.000 claims description 2
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- LHHDATRNVWNYKC-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(4-thiophen-3-ylfuran-2-yl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(OC=1)=CC=1C=1C=CSC=1 LHHDATRNVWNYKC-UHFFFAOYSA-N 0.000 claims description 2
- HSLQOYKHBCLWOB-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(4-thiophen-3-ylphenyl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C=C1)=CC=C1C=1C=CSC=1 HSLQOYKHBCLWOB-UHFFFAOYSA-N 0.000 claims description 2
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- CLBALKICHJMDDY-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(5-thiophen-2-ylthiophen-2-yl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(S1)=CC=C1C1=CC=CS1 CLBALKICHJMDDY-UHFFFAOYSA-N 0.000 claims description 2
- ADRZDHXTXVMBOR-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(5-thiophen-3-ylfuran-2-yl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(O1)=CC=C1C=1C=CSC=1 ADRZDHXTXVMBOR-UHFFFAOYSA-N 0.000 claims description 2
- AJJFWAVQFNELFJ-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(5-thiophen-3-ylfuran-3-yl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C=1)=COC=1C=1C=CSC=1 AJJFWAVQFNELFJ-UHFFFAOYSA-N 0.000 claims description 2
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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
-
- 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
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- 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
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- 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
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- 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
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- 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
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
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- 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
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- A—HUMAN NECESSITIES
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- A61P25/34—Tobacco-abuse
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- 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
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- 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)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
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- Neurology (AREA)
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- Addiction (AREA)
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- Epidemiology (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Steroid Compounds (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (3)
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| SE0202430-5 | 2002-08-14 | ||
| SE0202430A SE0202430D0 (sv) | 2002-08-14 | 2002-08-14 | New Compounds |
| PCT/SE2003/001277 WO2004016617A1 (en) | 2002-08-14 | 2003-08-13 | Biaryl diazabicycloalkane amides as nicotinic acetylcholine agonists |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2493920A1 true CA2493920A1 (en) | 2004-02-26 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002493920A Abandoned CA2493920A1 (en) | 2002-08-14 | 2003-08-13 | Biaryl diazabicycloalkane amides as nicotinic acetylcholine agonists |
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| EP (1) | EP1539765B1 (enExample) |
| JP (1) | JP2006507241A (enExample) |
| KR (1) | KR20060002727A (enExample) |
| CN (1) | CN100343256C (enExample) |
| AT (1) | ATE417049T1 (enExample) |
| AU (1) | AU2003248592B2 (enExample) |
| BR (1) | BR0313234A (enExample) |
| CA (1) | CA2493920A1 (enExample) |
| DE (1) | DE60325234D1 (enExample) |
| ES (1) | ES2316848T3 (enExample) |
| IL (1) | IL166416A0 (enExample) |
| MX (1) | MXPA05001583A (enExample) |
| NO (1) | NO20051259L (enExample) |
| NZ (1) | NZ537882A (enExample) |
| SE (1) | SE0202430D0 (enExample) |
| WO (1) | WO2004016617A1 (enExample) |
| ZA (1) | ZA200501226B (enExample) |
Families Citing this family (48)
| Publication number | Priority date | Publication date | Assignee | Title |
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| SE521512C2 (sv) | 2001-06-25 | 2003-11-11 | Niconovum Ab | Anordning för administrering av en substans till främre delen av en individs munhåla |
| DE10164139A1 (de) | 2001-12-27 | 2003-07-10 | Bayer Ag | 2-Heteroarylcarbonsäureamide |
| SE0202465D0 (sv) * | 2002-08-14 | 2002-08-14 | Astrazeneca Ab | New compounds |
| AU2003276919B2 (en) | 2002-09-25 | 2013-05-16 | Memory Pharmaceuticals Corporation | Indazoles, benzothiazoles, and benzoisothiazoles, and preparation and uses thereof |
| CA2511185C (en) | 2002-12-20 | 2012-09-18 | Niconovum Ab | A physically and chemically stable nicotine-containing particulate material |
| MXPA05006861A (es) * | 2003-02-27 | 2005-12-12 | Neurosearch As | Derivados arildiazabiciclicos novedosos. |
| WO2005063767A2 (en) | 2003-12-22 | 2005-07-14 | Memory Pharmaceuticals Corporation | Indoles, 1h-indazoles, 1,2-benzisoxazoles, and 1,2-benzisothiazoles, and preparation and uses thereof |
| JP2007515480A (ja) * | 2003-12-22 | 2007-06-14 | アストラゼネカ・アクチエボラーグ | ニコチン性アセチルコリンレセプターリガンド |
| TW200529860A (en) * | 2003-12-22 | 2005-09-16 | Astrazeneca Ab | Nicotinic acetylcholine receptor ligands |
| JP2007520527A (ja) * | 2004-02-04 | 2007-07-26 | ノイロサーチ アクティーゼルスカブ | ニコチン性アセチルコリン受容体リガンドとしてのジアザ２環式アリール誘導体 |
| US20050234095A1 (en) | 2004-03-25 | 2005-10-20 | Wenge Xie | Indazoles, benzothiazoles, benzoisothiazoles, benzisoxazoles, and preparation and uses thereof |
| JP2007534692A (ja) | 2004-04-22 | 2007-11-29 | メモリー・ファーマシューティカルズ・コーポレイション | インドール、１ｈ−インダゾール、１，２−ベンズイソキサゾール、１，２−ベンゾイソチアゾール、ならびにその調製および使用 |
| US7632831B2 (en) | 2004-05-07 | 2009-12-15 | Memory Pharmaceuticals Corporation | 1H-indazoles, benzothiazoles, 1,2-benzoisoxazoles, 1,2-benzoisothiazoles, and chromones and preparation and uses thereof |
| CN100588657C (zh) * | 2004-10-15 | 2010-02-10 | 神经研究公司 | 新的氮杂双环芳基衍生物及其医药用途 |
| RU2418797C2 (ru) | 2004-12-22 | 2011-05-20 | Мемори Фармасьютиклз Корпорейшн | Лиганды никотинового рецептора альфа-7, их получение и применение |
| US7855208B2 (en) | 2006-02-14 | 2010-12-21 | Neurosearch A/S | 3, 9-diazabicyclo(3.3.1)non-3-yl-aryl methanone derivatives as nicotinic acetylcholine receptor agonists |
| JP5694645B2 (ja) | 2006-03-16 | 2015-04-01 | ニコノヴァム エービーＮｉｃｏｎｏｖｕｍ Ａｂ | 改善された嗅ぎたばこ組成物 |
| EP2049538A1 (en) | 2006-05-30 | 2009-04-22 | NeuroSearch A/S | Novel 1,4-diaza-bicyclo[3.2.2]nonyl pyrimidinyl derivatives and their medical use |
| TWI454262B (zh) * | 2006-11-02 | 2014-10-01 | Targacept Inc | 菸鹼乙醯膽鹼受體亞型選擇性之二氮雜雙環烷類醯胺 |
| SA08290475B1 (ar) | 2007-08-02 | 2013-06-22 | Targacept Inc | (2s، 3r)-n-(2-((3-بيردينيل)ميثيل)-1-آزا بيسيكلو[2، 2، 2]أوكت-3-يل)بنزو فيوران-2-كربوكساميد، وصور أملاحه الجديدة وطرق استخدامه |
| US20100298306A1 (en) * | 2007-10-22 | 2010-11-25 | 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 |
| GB0724251D0 (en) | 2007-12-12 | 2008-02-06 | Univ Edinburgh | Therapeutic compounds and their use |
| GB0804685D0 (en) | 2008-03-13 | 2008-04-16 | Univ Edinburgh | Therapeutic compounds and their use |
| TWI488854B (zh) | 2008-06-20 | 2015-06-21 | Astrazeneca Ab | 二苯并噻氮呯衍生物及其用途 |
| TW201031664A (en) | 2009-01-26 | 2010-09-01 | Targacept Inc | Preparation and therapeutic applications of (2S,3R)-N-2-((3-pyridinyl)methyl)-1-azabicyclo[2.2.2]oct-3-yl)-3,5-difluorobenzamide |
| WO2010146338A1 (en) | 2009-06-15 | 2010-12-23 | The University Of Edinburgh | Amido-isothiazole compounds and their use as inhibitors of 11beta-hsd1 for the treatment of metabolic syndrome and related disorders |
| AU2010297068B2 (en) | 2009-09-16 | 2015-10-01 | The University Of Edinburgh | (4-phenyl-piperidin-1-yl)-[5-1H-pyrazol-4yl)-thiophen-3-yl]-methanone compounds and their use |
| CA2826623A1 (en) * | 2010-02-03 | 2011-08-11 | Meh Associates, Inc | Multiple substituted fluoromethanes as selective and bioactive isosteres |
| KR101714820B1 (ko) | 2010-04-29 | 2017-03-09 | 더 유니버시티 오브 에든버러 | 11(베타)-ｈｓｄ1의 억제제로서 3,3-이치환된-(8-아자-비시클로[3.2.1]옥트-8-일)-[5-(1h-피라졸-4-일)-티오펜-3-일]-메탄온 |
| JP5749797B2 (ja) | 2010-05-17 | 2015-07-15 | フォルム ファーマシューティカルズ、インコーポレイテッド | （ｒ）−７−クロロ−ｎ−（キヌクリジン−３−イル）ベンゾ［ｂ］チオフェン−２−カルボキサミド塩酸塩一水和物の結晶形 |
| ES2603032T3 (es) * | 2010-07-15 | 2017-02-23 | Bayer Intellectual Property Gmbh | Compuestos de 3-piridil-heteroarilcarboxamida como pesticidas |
| GB201111704D0 (en) | 2011-07-07 | 2011-08-24 | Takeda Pharmaceutical | Novel compounds |
| GB201111705D0 (en) | 2011-07-07 | 2011-08-24 | Takeda Pharmaceutical | Compounds and their use |
| JO3115B1 (ar) | 2011-08-22 | 2017-09-20 | Takeda Pharmaceuticals Co | مركبات بيريدازينون واستخدامها كمثبطات daao |
| CA2872005A1 (en) | 2012-05-08 | 2013-11-14 | Forum Pharmaceuticals, Inc. | Methods of maintaining, treating or improving cognitive function |
| GB201209587D0 (en) | 2012-05-30 | 2012-07-11 | Takeda Pharmaceutical | Therapeutic compounds |
| MA37975B2 (fr) * | 2012-09-11 | 2021-03-31 | Genzyme Corp | Inhibiteurs de synthase de glucosylcéramide |
| JP6478923B2 (ja) | 2013-02-07 | 2019-03-06 | ヘプタレス セラピューティクス リミテッドＨｅｐｔａｒｅｓ Ｔｈｅｒａｐｅｕｔｉｃｓ Ｌｉｍｉｔｅｄ | ムスカリンｍ４受容体アゴニストとしてのピペリジン−１−イル及びアゼピン−１−イルカルボキシレート |
| EA029430B1 (ru) | 2013-06-21 | 2018-03-30 | Такеда Фармасьютикл Компани Лимитед | Производные 1-сульфонилпиперидина в качестве модуляторов рецепторов прокинетицина |
| GB201314286D0 (en) | 2013-08-08 | 2013-09-25 | Takeda Pharmaceutical | Therapeutic Compounds |
| GB201318222D0 (en) | 2013-10-15 | 2013-11-27 | Takeda Pharmaceutical | Novel compounds |
| GB201320905D0 (en) | 2013-11-27 | 2014-01-08 | Takeda Pharmaceutical | Therapeutic compounds |
| TW201613864A (en) | 2014-02-20 | 2016-04-16 | Takeda Pharmaceutical | Novel compounds |
| GB201616839D0 (en) | 2016-10-04 | 2016-11-16 | Takeda Pharmaceutical Company Limited | Therapeutic compounds |
| GB201619514D0 (en) | 2016-11-18 | 2017-01-04 | Takeda Pharmaceuticals Co | Novel compounds |
| US12083115B2 (en) | 2020-02-03 | 2024-09-10 | Genzyme Corporation | Methods for treating neurological symptoms associated with lysosomal storage diseases |
| JP2021138648A (ja) | 2020-03-04 | 2021-09-16 | 武田薬品工業株式会社 | 経口固形製剤 |
| BR112023000798A2 (pt) | 2020-07-24 | 2023-02-07 | Genzyme Corp | Composições farmacêuticas compreendendo venglustat |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3281423A (en) * | 1964-02-03 | 1966-10-25 | Merck & Co Inc | 1, 3-ethanopiperazines and process |
| 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 |
| FR2791678B1 (fr) * | 1999-03-30 | 2001-05-04 | Synthelabo | Derives de 1,4-diazabicyclo [3.2.2] nonane-4-carboxylates et -carboxamides, 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 |
| FR2809732B1 (fr) * | 2000-05-31 | 2002-07-19 | Sanofi Synthelabo | DERIVES DE 4(-2-PHENYLTHIAZOL-5-yl)-1,4-DIAZABICYCLO-[3.2.2] NONANE, LEUR PREPARATION ET LEUR APPLICATION ENTHERAPEUTIQUE |
| SE0202465D0 (sv) * | 2002-08-14 | 2002-08-14 | Astrazeneca Ab | New compounds |
| MXPA05006861A (es) * | 2003-02-27 | 2005-12-12 | Neurosearch As | Derivados arildiazabiciclicos novedosos. |
| TW200529860A (en) * | 2003-12-22 | 2005-09-16 | Astrazeneca Ab | Nicotinic acetylcholine receptor ligands |
| JP2007515480A (ja) * | 2003-12-22 | 2007-06-14 | アストラゼネカ・アクチエボラーグ | ニコチン性アセチルコリンレセプターリガンド |
-
2002
- 2002-08-14 SE SE0202430A patent/SE0202430D0/xx unknown
-
2003
- 2003-08-13 BR BR0313234-0A patent/BR0313234A/pt not_active IP Right Cessation
- 2003-08-13 DE DE60325234T patent/DE60325234D1/de not_active Expired - Fee Related
- 2003-08-13 CA CA002493920A patent/CA2493920A1/en not_active Abandoned
- 2003-08-13 US US10/524,484 patent/US20050239774A1/en not_active Abandoned
- 2003-08-13 CN CNB038194791A patent/CN100343256C/zh not_active Expired - Fee Related
- 2003-08-13 KR KR1020057002265A patent/KR20060002727A/ko not_active Ceased
- 2003-08-13 ES ES03788214T patent/ES2316848T3/es not_active Expired - Lifetime
- 2003-08-13 WO PCT/SE2003/001277 patent/WO2004016617A1/en not_active Ceased
- 2003-08-13 AU AU2003248592A patent/AU2003248592B2/en not_active Expired - Fee Related
- 2003-08-13 NZ NZ537882A patent/NZ537882A/en unknown
- 2003-08-13 AT AT03788214T patent/ATE417049T1/de not_active IP Right Cessation
- 2003-08-13 JP JP2004529002A patent/JP2006507241A/ja active Pending
- 2003-08-13 MX MXPA05001583A patent/MXPA05001583A/es unknown
- 2003-08-13 EP EP03788214A patent/EP1539765B1/en not_active Expired - Lifetime
-
2005
- 2005-01-20 IL IL16641605A patent/IL166416A0/xx unknown
- 2005-02-10 ZA ZA200501226A patent/ZA200501226B/en unknown
- 2005-03-11 NO NO20051259A patent/NO20051259L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| NZ537882A (en) | 2008-02-29 |
| EP1539765B1 (en) | 2008-12-10 |
| WO2004016617A1 (en) | 2004-02-26 |
| ZA200501226B (en) | 2006-07-26 |
| CN100343256C (zh) | 2007-10-17 |
| MXPA05001583A (es) | 2005-04-25 |
| ES2316848T3 (es) | 2009-04-16 |
| AU2003248592B2 (en) | 2008-04-03 |
| US20050239774A1 (en) | 2005-10-27 |
| CN1678615A (zh) | 2005-10-05 |
| KR20060002727A (ko) | 2006-01-09 |
| EP1539765A1 (en) | 2005-06-15 |
| ATE417049T1 (de) | 2008-12-15 |
| JP2006507241A (ja) | 2006-03-02 |
| BR0313234A (pt) | 2005-06-14 |
| AU2003248592A1 (en) | 2004-03-03 |
| SE0202430D0 (sv) | 2002-08-14 |
| HK1077571A1 (en) | 2006-02-17 |
| NO20051259L (no) | 2005-05-12 |
| DE60325234D1 (de) | 2009-01-22 |
| IL166416A0 (en) | 2006-01-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued | ||
| FZDE | Discontinued |
Effective date: 20090813 |