NO327882B1 - Terapeutisk aktive cyklopropanforbindelser, fremsgangsmater for fremstilling derav, farmasoytiske sammensetninger inneholdende disse samt anvendelse derav for fremstilling av farmasoytiske sammensetninger. - Google Patents
Terapeutisk aktive cyklopropanforbindelser, fremsgangsmater for fremstilling derav, farmasoytiske sammensetninger inneholdende disse samt anvendelse derav for fremstilling av farmasoytiske sammensetninger. Download PDFInfo
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- NO327882B1 NO327882B1 NO20013206A NO20013206A NO327882B1 NO 327882 B1 NO327882 B1 NO 327882B1 NO 20013206 A NO20013206 A NO 20013206A NO 20013206 A NO20013206 A NO 20013206A NO 327882 B1 NO327882 B1 NO 327882B1
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- formula
- compounds
- methyl
- compound
- defined above
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- 238000002360 preparation method Methods 0.000 title claims description 53
- 238000000034 method Methods 0.000 title claims description 44
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 14
- 125000001559 cyclopropyl group Chemical class [H]C1([H])C([H])([H])C1([H])* 0.000 title claims description 4
- 230000008569 process Effects 0.000 title claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 246
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 42
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 33
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 30
- -1 6-methyl-3-pyridyl Chemical group 0.000 claims description 29
- 238000011282 treatment Methods 0.000 claims description 23
- 238000003786 synthesis reaction Methods 0.000 claims description 17
- 239000002585 base Substances 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 14
- 230000009471 action Effects 0.000 claims description 14
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 13
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 230000032683 aging Effects 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 208000024827 Alzheimer disease Diseases 0.000 claims description 8
- 230000015654 memory Effects 0.000 claims description 8
- 125000004076 pyridyl group Chemical group 0.000 claims description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 8
- 230000002490 cerebral effect Effects 0.000 claims description 7
- 230000006870 function Effects 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 125000006239 protecting group Chemical group 0.000 claims description 7
- 208000019022 Mood disease Diseases 0.000 claims description 6
- 239000003638 chemical reducing agent Substances 0.000 claims description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
- 206010012289 Dementia Diseases 0.000 claims description 5
- 241000208125 Nicotiana Species 0.000 claims description 5
- 235000002637 Nicotiana tabacum Nutrition 0.000 claims description 5
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- 239000004480 active ingredient Substances 0.000 claims description 5
- 230000004770 neurodegeneration Effects 0.000 claims description 5
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- CJGBNCHBOUXRCE-UHFFFAOYSA-N 1-(pyridin-3-yloxymethyl)cyclopropan-1-amine;dihydrochloride Chemical compound Cl.Cl.C=1C=CN=CC=1OCC1(N)CC1 CJGBNCHBOUXRCE-UHFFFAOYSA-N 0.000 claims description 4
- 201000011240 Frontotemporal dementia Diseases 0.000 claims description 4
- 208000006264 Korsakoff syndrome Diseases 0.000 claims description 4
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- 208000016620 Tourette disease Diseases 0.000 claims description 4
- 238000007239 Wittig reaction Methods 0.000 claims description 4
- 230000001476 alcoholic effect Effects 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 210000001652 frontal lobe Anatomy 0.000 claims description 4
- 239000007800 oxidant agent Substances 0.000 claims description 4
- 238000000926 separation method Methods 0.000 claims description 4
- 230000002739 subcortical effect Effects 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- NROFPBCWYYRUBC-WLHGVMLRSA-N (e)-but-2-enedioic acid;3-[1-(dimethylamino)cyclopropyl]propyl n,n-dimethylcarbamate Chemical compound OC(=O)\C=C\C(O)=O.CN(C)C(=O)OCCCC1(N(C)C)CC1 NROFPBCWYYRUBC-WLHGVMLRSA-N 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 231100000252 nontoxic Toxicity 0.000 claims description 3
- 230000003000 nontoxic effect Effects 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 239000007858 starting material Substances 0.000 claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 2
- 208000026139 Memory disease Diseases 0.000 claims description 2
- 229910006124 SOCl2 Inorganic materials 0.000 claims description 2
- XTPOCSLNWOQFCX-UHFFFAOYSA-N [1-(dimethylamino)cyclopropyl]methyl n,n-dimethylcarbamate Chemical compound CN(C)C(=O)OCC1(N(C)C)CC1 XTPOCSLNWOQFCX-UHFFFAOYSA-N 0.000 claims description 2
- 150000001412 amines Chemical group 0.000 claims description 2
- UPKOQJDZNGRHAO-UHFFFAOYSA-N n,n-dimethyl-1-(2-pyridin-3-yloxyethyl)cyclopropan-1-amine Chemical compound C=1C=CN=CC=1OCCC1(N(C)C)CC1 UPKOQJDZNGRHAO-UHFFFAOYSA-N 0.000 claims description 2
- 150000003141 primary amines Chemical group 0.000 claims description 2
- 230000003252 repetitive effect Effects 0.000 claims description 2
- 230000002950 deficient Effects 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims 2
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims 2
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims 2
- 229940079593 drug Drugs 0.000 claims 2
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 1
- SXAKIOIIBBZBFN-UHFFFAOYSA-N 2-[1-(dimethylamino)cyclopropyl]ethyl n,n-dimethylcarbamate Chemical compound CN(C)C(=O)OCCC1(N(C)C)CC1 SXAKIOIIBBZBFN-UHFFFAOYSA-N 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- WFFWTOZFBBKQEL-UHFFFAOYSA-N n,n-dimethyl-1-(pyridin-3-yloxymethyl)cyclopropan-1-amine Chemical compound C=1C=CN=CC=1OCC1(N(C)C)CC1 WFFWTOZFBBKQEL-UHFFFAOYSA-N 0.000 claims 1
- 238000000746 purification Methods 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 117
- 239000000047 product Substances 0.000 description 105
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 88
- 239000000243 solution Substances 0.000 description 76
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 74
- 239000000203 mixture Substances 0.000 description 49
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
- 238000002844 melting Methods 0.000 description 45
- 230000008018 melting Effects 0.000 description 45
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 37
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 29
- 239000000741 silica gel Substances 0.000 description 29
- 229910002027 silica gel Inorganic materials 0.000 description 29
- 238000004587 chromatography analysis Methods 0.000 description 27
- 239000000758 substrate Substances 0.000 description 27
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- 102000019315 Nicotinic acetylcholine receptors Human genes 0.000 description 18
- 108050006807 Nicotinic acetylcholine receptors Proteins 0.000 description 18
- 238000010992 reflux Methods 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 16
- 241000700159 Rattus Species 0.000 description 16
- 239000012074 organic phase Substances 0.000 description 16
- 238000003756 stirring Methods 0.000 description 16
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 239000011541 reaction mixture Substances 0.000 description 15
- 241001465754 Metazoa Species 0.000 description 14
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 238000007792 addition Methods 0.000 description 12
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 11
- 229960002715 nicotine Drugs 0.000 description 11
- 229910000029 sodium carbonate Inorganic materials 0.000 description 11
- 239000012528 membrane Substances 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 9
- 239000008346 aqueous phase Substances 0.000 description 9
- 210000004556 brain Anatomy 0.000 description 9
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 9
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- YECIFGHRMFEPJK-UHFFFAOYSA-N lidocaine hydrochloride monohydrate Chemical compound O.[Cl-].CC[NH+](CC)CC(=O)NC1=C(C)C=CC=C1C YECIFGHRMFEPJK-UHFFFAOYSA-N 0.000 description 8
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 8
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 7
- GRFNBEZIAWKNCO-UHFFFAOYSA-N 3-pyridinol Chemical compound OC1=CC=CN=C1 GRFNBEZIAWKNCO-UHFFFAOYSA-N 0.000 description 6
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 6
- 229960004373 acetylcholine Drugs 0.000 description 6
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- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 102000005962 receptors Human genes 0.000 description 6
- 108020003175 receptors Proteins 0.000 description 6
- 229910000104 sodium hydride Inorganic materials 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 238000010626 work up procedure Methods 0.000 description 6
- 102000014415 Muscarinic acetylcholine receptor Human genes 0.000 description 5
- 108050003473 Muscarinic acetylcholine receptor Proteins 0.000 description 5
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- 230000027455 binding Effects 0.000 description 5
- 238000010790 dilution Methods 0.000 description 5
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- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 239000001530 fumaric acid Substances 0.000 description 5
- 230000009871 nonspecific binding Effects 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
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- 208000004998 Abdominal Pain Diseases 0.000 description 4
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- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- 230000006735 deficit Effects 0.000 description 4
- 150000003840 hydrochlorides Chemical group 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
- 230000000144 pharmacologic effect Effects 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
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- 239000000725 suspension Substances 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 description 4
- 230000001225 therapeutic effect Effects 0.000 description 4
- IZYOHLOUZVEIOS-UHFFFAOYSA-N 1-methoxycarbonylcyclopropane-1-carboxylic acid Chemical compound COC(=O)C1(C(O)=O)CC1 IZYOHLOUZVEIOS-UHFFFAOYSA-N 0.000 description 3
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- FVIGODVHAVLZOO-UHFFFAOYSA-N Dixanthogen Chemical compound CCOC(=S)SSC(=S)OCC FVIGODVHAVLZOO-UHFFFAOYSA-N 0.000 description 3
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- MKRTXPORKIRPDG-UHFFFAOYSA-N diphenylphosphoryl azide Chemical compound C=1C=CC=CC=1P(=O)(N=[N+]=[N-])C1=CC=CC=C1 MKRTXPORKIRPDG-UHFFFAOYSA-N 0.000 description 3
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- 125000001424 substituent group Chemical group 0.000 description 3
- WNGRWEFUIAQVHA-UHFFFAOYSA-N (1-pyrrolidin-1-ylcyclopropyl)methanol Chemical compound C1CCCN1C1(CO)CC1 WNGRWEFUIAQVHA-UHFFFAOYSA-N 0.000 description 2
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- AZPVWIZXXORHAU-WLHGVMLRSA-N (e)-but-2-enedioic acid;n-methyl-1-(2-pyridin-3-yloxyethyl)cyclopropan-1-amine Chemical compound OC(=O)\C=C\C(O)=O.C=1C=CN=CC=1OCCC1(NC)CC1 AZPVWIZXXORHAU-WLHGVMLRSA-N 0.000 description 2
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- HVPITLNEDNJGML-UHFFFAOYSA-N 1-[(dimethylamino)methyl]cyclopropan-1-ol;hydrochloride Chemical compound Cl.CN(C)CC1(O)CC1 HVPITLNEDNJGML-UHFFFAOYSA-N 0.000 description 2
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- HOPIFNRCPXUXRE-UHFFFAOYSA-N 3-[1-(dimethylamino)cyclopropyl]propan-1-ol Chemical compound OCCCC1(N(C)C)CC1 HOPIFNRCPXUXRE-UHFFFAOYSA-N 0.000 description 2
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- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
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- KIIGJJYGCDEDRR-UHFFFAOYSA-N methyl 1-(methoxycarbonylamino)cyclopropane-1-carboxylate Chemical compound COC(=O)NC1(C(=O)OC)CC1 KIIGJJYGCDEDRR-UHFFFAOYSA-N 0.000 description 1
- ACXGDYTVQAXJHI-UHFFFAOYSA-N methyl 1-[(2-methylpropan-2-yl)oxycarbonylamino]cyclopropane-1-carboxylate Chemical compound CC(C)(C)OC(=O)NC1(C(=O)OC)CC1 ACXGDYTVQAXJHI-UHFFFAOYSA-N 0.000 description 1
- NWAONVVCKNYSPG-UHFFFAOYSA-N methyl 1-[methoxycarbonyl(methyl)amino]cyclopropane-1-carboxylate Chemical compound COC(=O)N(C)C1(C(=O)OC)CC1 NWAONVVCKNYSPG-UHFFFAOYSA-N 0.000 description 1
- LAXOTRWQWYZIQE-UHFFFAOYSA-N methyl 1-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]cyclopropane-1-carboxylate Chemical compound CC(C)(C)OC(=O)N(C)C1(C(=O)OC)CC1 LAXOTRWQWYZIQE-UHFFFAOYSA-N 0.000 description 1
- ULMBPGYSCZOWNE-UHFFFAOYSA-N methyl 2-(1-aminocyclopropyl)acetate Chemical compound COC(=O)CC1(N)CC1 ULMBPGYSCZOWNE-UHFFFAOYSA-N 0.000 description 1
- DNJAQFMFCFOOQT-UHFFFAOYSA-N methyl 2-[1-(2,5-dioxopyrrolidin-1-yl)cyclopropyl]acetate Chemical compound O=C1CCC(=O)N1C1(CC(=O)OC)CC1 DNJAQFMFCFOOQT-UHFFFAOYSA-N 0.000 description 1
- HEMWGLXLUBLRTN-UHFFFAOYSA-N methyl 2-[1-(dimethylamino)cyclopropyl]acetate Chemical compound COC(=O)CC1(N(C)C)CC1 HEMWGLXLUBLRTN-UHFFFAOYSA-N 0.000 description 1
- HVOOKJCMCQKIJL-UHFFFAOYSA-N methyl 2-[1-(methylamino)cyclopropyl]acetate Chemical compound COC(=O)CC1(NC)CC1 HVOOKJCMCQKIJL-UHFFFAOYSA-N 0.000 description 1
- 230000003551 muscarinic effect Effects 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- OCWNCEHLQPGCCT-UHFFFAOYSA-N n,n-dimethyl-1-(2-pyridin-3-ylethyl)cyclopropan-1-amine;hydrochloride Chemical compound Cl.C=1C=CN=CC=1CCC1(N(C)C)CC1 OCWNCEHLQPGCCT-UHFFFAOYSA-N 0.000 description 1
- VAMJPKXPJSXAPF-UHFFFAOYSA-N n,n-dimethyl-1-(2-pyridin-3-yloxyethyl)cyclopropan-1-amine;dihydrochloride Chemical compound Cl.Cl.C=1C=CN=CC=1OCCC1(N(C)C)CC1 VAMJPKXPJSXAPF-UHFFFAOYSA-N 0.000 description 1
- CALNBNTWFIWFOH-UHFFFAOYSA-N n,n-dimethyl-1-(pyridin-3-yloxymethyl)cyclopropan-1-amine;hydrochloride Chemical compound Cl.C=1C=CN=CC=1OCC1(N(C)C)CC1 CALNBNTWFIWFOH-UHFFFAOYSA-N 0.000 description 1
- JEDHEXUPBRMUMB-UHFFFAOYSA-N n,n-dimethylpyridin-3-amine Chemical compound CN(C)C1=CC=CN=C1 JEDHEXUPBRMUMB-UHFFFAOYSA-N 0.000 description 1
- UJOAZUXLEGDYJY-UHFFFAOYSA-N n-methyl-1-(2-pyridin-3-ylethyl)cyclopropan-1-amine;dihydrochloride Chemical compound Cl.Cl.C=1C=CN=CC=1CCC1(NC)CC1 UJOAZUXLEGDYJY-UHFFFAOYSA-N 0.000 description 1
- JQSBIGAAHYMBFX-UHFFFAOYSA-N n-methyl-1-(pyridin-3-yloxymethyl)cyclopropan-1-amine Chemical compound C=1C=CN=CC=1OCC1(NC)CC1 JQSBIGAAHYMBFX-UHFFFAOYSA-N 0.000 description 1
- PLBXUIATHCUOIH-UHFFFAOYSA-N n-methyl-1-(pyridin-3-yloxymethyl)cyclopropan-1-amine;hydrochloride Chemical compound Cl.C=1C=CN=CC=1OCC1(NC)CC1 PLBXUIATHCUOIH-UHFFFAOYSA-N 0.000 description 1
- NDRSHLNLKPMLHR-UHFFFAOYSA-N n-methyl-1-[(6-methylpyridin-3-yl)oxymethyl]cyclopropan-1-amine;hydrochloride Chemical compound Cl.C=1C=C(C)N=CC=1OCC1(NC)CC1 NDRSHLNLKPMLHR-UHFFFAOYSA-N 0.000 description 1
- 229960002362 neostigmine Drugs 0.000 description 1
- LULNWZDBKTWDGK-UHFFFAOYSA-M neostigmine bromide Chemical compound [Br-].CN(C)C(=O)OC1=CC=CC([N+](C)(C)C)=C1 LULNWZDBKTWDGK-UHFFFAOYSA-M 0.000 description 1
- 230000010004 neural pathway Effects 0.000 description 1
- 210000002569 neuron Anatomy 0.000 description 1
- 230000000324 neuroprotective effect Effects 0.000 description 1
- 239000000181 nicotinic agonist Substances 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 238000011017 operating method Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 230000001242 postsynaptic effect Effects 0.000 description 1
- 210000002442 prefrontal cortex Anatomy 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- WHMDPDGBKYUEMW-UHFFFAOYSA-N pyridine-2-thiol Chemical compound SC1=CC=CC=N1 WHMDPDGBKYUEMW-UHFFFAOYSA-N 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 201000000980 schizophrenia Diseases 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- WHYQZPOBOBSAIS-UHFFFAOYSA-M sodium;pyridin-3-olate Chemical compound [Na+].[O-]C1=CC=CN=C1 WHYQZPOBOBSAIS-UHFFFAOYSA-M 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 239000006190 sub-lingual tablet Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 238000007910 systemic administration Methods 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- BINGWTOENXKHEV-VOTSOKGWSA-N tert-butyl (e)-3-pyridin-3-ylprop-2-enoate Chemical compound CC(C)(C)OC(=O)\C=C\C1=CC=CN=C1 BINGWTOENXKHEV-VOTSOKGWSA-N 0.000 description 1
- DGKXCTZLDVTPPL-UHFFFAOYSA-N tert-butyl n-(1-formylcyclopropyl)-n-methylcarbamate Chemical compound CC(C)(C)OC(=O)N(C)C1(C=O)CC1 DGKXCTZLDVTPPL-UHFFFAOYSA-N 0.000 description 1
- BESSNJVSPVAKNI-UHFFFAOYSA-N tert-butyl n-[1-(bromomethyl)cyclopropyl]carbamate Chemical compound CC(C)(C)OC(=O)NC1(CBr)CC1 BESSNJVSPVAKNI-UHFFFAOYSA-N 0.000 description 1
- NSEYYNDTDRCALO-UHFFFAOYSA-N tert-butyl n-[1-(cyanomethyl)cyclopropyl]-n-methylcarbamate Chemical compound CC(C)(C)OC(=O)N(C)C1(CC#N)CC1 NSEYYNDTDRCALO-UHFFFAOYSA-N 0.000 description 1
- HEILYIARKHMAGU-UHFFFAOYSA-N tert-butyl n-[1-(cyanomethyl)cyclopropyl]carbamate Chemical compound CC(C)(C)OC(=O)NC1(CC#N)CC1 HEILYIARKHMAGU-UHFFFAOYSA-N 0.000 description 1
- HFMAZNJKNNRONT-UHFFFAOYSA-N tert-butyl n-[1-(hydroxymethyl)cyclopropyl]carbamate Chemical compound CC(C)(C)OC(=O)NC1(CO)CC1 HFMAZNJKNNRONT-UHFFFAOYSA-N 0.000 description 1
- JODRRAFVPNPUJD-UHFFFAOYSA-N tert-butyl n-methyl-n-[1-(2-pyridin-3-ylethyl)cyclopropyl]carbamate Chemical compound C=1C=CN=CC=1CCC1(N(C(=O)OC(C)(C)C)C)CC1 JODRRAFVPNPUJD-UHFFFAOYSA-N 0.000 description 1
- WQFQHVWVMNIDMJ-UHFFFAOYSA-N tert-butyl n-methyl-n-[1-(2-pyridin-3-yloxyethyl)cyclopropyl]carbamate Chemical compound C=1C=CN=CC=1OCCC1(N(C(=O)OC(C)(C)C)C)CC1 WQFQHVWVMNIDMJ-UHFFFAOYSA-N 0.000 description 1
- UMBRAZCWUFROGY-FPLPWBNLSA-N tert-butyl n-methyl-n-[1-[(z)-2-pyridin-3-ylethenyl]cyclopropyl]carbamate Chemical compound C=1C=CN=CC=1\C=C/C1(N(C(=O)OC(C)(C)C)C)CC1 UMBRAZCWUFROGY-FPLPWBNLSA-N 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- YFOFTOVBTCVSGV-UHFFFAOYSA-M triphenyl(pyridin-3-ylmethyl)phosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)CC1=CC=CN=C1 YFOFTOVBTCVSGV-UHFFFAOYSA-M 0.000 description 1
- IIHPVYJPDKJYOU-UHFFFAOYSA-N triphenylcarbethoxymethylenephosphorane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=CC(=O)OCC)C1=CC=CC=C1 IIHPVYJPDKJYOU-UHFFFAOYSA-N 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
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
- C07D213/60—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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/70—Sulfur atoms
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- 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
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/44—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and containing rings
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- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/52—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups or amino groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
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- C07C219/00—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C219/02—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C219/18—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and containing rings
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- C07C219/00—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/12—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
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- C07C271/06—Esters of carbamic acids
- C07C271/32—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C271/34—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of rings other than six-membered aromatic rings with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
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- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/24—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/26—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being saturated and containing rings
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- 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
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- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/096—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
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- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
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Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR0008203A FR2810664B1 (fr) | 2000-06-27 | 2000-06-27 | Nouveaux composes cyclopropaniques 1,1 et 1,2-dissubstitues, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
Publications (3)
Publication Number | Publication Date |
---|---|
NO20013206D0 NO20013206D0 (no) | 2001-06-26 |
NO20013206L NO20013206L (no) | 2001-12-28 |
NO327882B1 true NO327882B1 (no) | 2009-10-12 |
Family
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO20013206A NO327882B1 (no) | 2000-06-27 | 2001-06-26 | Terapeutisk aktive cyklopropanforbindelser, fremsgangsmater for fremstilling derav, farmasoytiske sammensetninger inneholdende disse samt anvendelse derav for fremstilling av farmasoytiske sammensetninger. |
Country Status (23)
Country | Link |
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US (2) | US6943184B2 (da) |
EP (1) | EP1170281B1 (da) |
JP (2) | JP3720735B2 (da) |
KR (1) | KR100450315B1 (da) |
CN (1) | CN1176066C (da) |
AR (1) | AR029537A1 (da) |
AT (1) | ATE313524T1 (da) |
AU (1) | AU777733B2 (da) |
BR (1) | BR0102587A (da) |
CA (1) | CA2351833C (da) |
DE (1) | DE60115997T2 (da) |
DK (1) | DK1170281T3 (da) |
EA (1) | EA005185B1 (da) |
ES (1) | ES2254344T3 (da) |
FR (1) | FR2810664B1 (da) |
HK (1) | HK1041605B (da) |
HU (1) | HUP0102631A3 (da) |
MX (1) | MXPA01006586A (da) |
NO (1) | NO327882B1 (da) |
NZ (1) | NZ512605A (da) |
PL (1) | PL202459B1 (da) |
SI (1) | SI1170281T1 (da) |
ZA (1) | ZA200105300B (da) |
Families Citing this family (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE10164139A1 (de) | 2001-12-27 | 2003-07-10 | Bayer Ag | 2-Heteroarylcarbonsäureamide |
FR2889188B1 (fr) * | 2005-07-28 | 2007-09-07 | Servier Lab | Nouveaux composes 1,1-pyridinylaminocyclopropanamines polysubstitues, leur procede de preparation et les compositions phamaceutiques qui les contiennent |
FR2889187B1 (fr) * | 2005-07-28 | 2007-09-07 | Servier Lab | Nouveaux composes 1,1-pyridinyloxycyclopropanamines polysusbstitues, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
FR2896800B1 (fr) * | 2006-01-30 | 2008-04-11 | Servier Lab | Nouveaux composes pyridinylaminoalkylene-et pyridinyloxyalkylene-cyclopropanamines polysubstitues, leur procede de preparation et les compositions pharmaceutiques qui les contiennent. |
KR100718472B1 (ko) * | 2006-04-10 | 2007-05-18 | 김동현 | 걸레 세척장치 |
CA2894860C (en) | 2008-11-19 | 2018-11-06 | Gerhard Koenig | Treatment of cognitive disorders with (r)-7-chloro-n-(quinuclidin-3-yl)benzo[b]thiophene-2-carboxamide and pharmaceutically acceptable salts thereof |
JP5808319B2 (ja) * | 2009-05-11 | 2015-11-10 | 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 | アセチルコリンエステラーゼ阻害剤と組み合わせた特定のα7ニコチン酸受容体を用いた認知障害の治療 |
KR101495978B1 (ko) | 2010-05-17 | 2015-02-25 | 포럼 파마슈티칼즈 인크. | (R)-7-클로로-N-(퀴누클리딘-3-일)벤조[b]티오펜-2-카르복사미드 히드로클로리드 모노히드레이트의 결정질 형태 |
EP3461481A1 (en) | 2012-05-08 | 2019-04-03 | Forum Pharmaceuticals Inc. | Methods of maintaining, treating or improving cognitive function |
CN104119235B (zh) * | 2014-07-30 | 2015-11-11 | 天津市斯芬克司药物研发有限公司 | 一种环丙基甲胺化合物及其制备方法 |
CR20180452A (es) * | 2016-03-22 | 2019-02-06 | Merck Sharp & Dohme | Moduladores alostéricos de receptores de acetilcolina nicotícos |
CN111848423B (zh) * | 2019-04-30 | 2022-10-14 | 尚科生物医药(上海)有限公司 | 3-氧代环丁基氨基甲酸叔丁酯的制备方法 |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB951461A (en) * | 1959-11-17 | 1964-03-04 | Smith Kline French Lab | Improvements in or relating to substituted 2-phenoxy-cyclopropylamines |
FR1315433A (fr) * | 1962-02-19 | 1963-01-18 | Hoffmann La Roche | Procédé pour la préparation d'amines cycliques |
US3156725A (en) * | 1962-04-18 | 1964-11-10 | Smith Kline French Lab | Substituted 2-phenoxy and phenylthio-cyclopropylamines |
IN158970B (da) * | 1981-06-09 | 1987-02-28 | Ici Plc | |
WO1996025160A1 (en) * | 1995-02-17 | 1996-08-22 | Novo Nordisk A/S | The use of heterocyclic compounds |
CA2190699A1 (en) * | 1995-12-08 | 1997-06-09 | Johannes Aebi | Tertiary amines |
-
2000
- 2000-06-27 FR FR0008203A patent/FR2810664B1/fr not_active Expired - Fee Related
-
2001
- 2001-06-25 AR ARP010103003A patent/AR029537A1/es unknown
- 2001-06-25 JP JP2001191541A patent/JP3720735B2/ja not_active Expired - Fee Related
- 2001-06-26 SI SI200130472T patent/SI1170281T1/sl unknown
- 2001-06-26 EP EP01401677A patent/EP1170281B1/fr not_active Expired - Lifetime
- 2001-06-26 NZ NZ512605A patent/NZ512605A/en unknown
- 2001-06-26 DE DE60115997T patent/DE60115997T2/de not_active Expired - Fee Related
- 2001-06-26 US US09/888,990 patent/US6943184B2/en not_active Expired - Fee Related
- 2001-06-26 AT AT01401677T patent/ATE313524T1/de not_active IP Right Cessation
- 2001-06-26 MX MXPA01006586A patent/MXPA01006586A/es active IP Right Grant
- 2001-06-26 NO NO20013206A patent/NO327882B1/no not_active IP Right Cessation
- 2001-06-26 DK DK01401677T patent/DK1170281T3/da active
- 2001-06-26 ES ES01401677T patent/ES2254344T3/es not_active Expired - Lifetime
- 2001-06-27 EA EA200100597A patent/EA005185B1/ru not_active IP Right Cessation
- 2001-06-27 CA CA002351833A patent/CA2351833C/fr not_active Expired - Fee Related
- 2001-06-27 ZA ZA200105300A patent/ZA200105300B/xx unknown
- 2001-06-27 CN CNB011218312A patent/CN1176066C/zh not_active Expired - Fee Related
- 2001-06-27 BR BR0102587-2A patent/BR0102587A/pt not_active IP Right Cessation
- 2001-06-27 HU HU0102631A patent/HUP0102631A3/hu unknown
- 2001-06-27 KR KR10-2001-0036982A patent/KR100450315B1/ko not_active IP Right Cessation
- 2001-06-27 PL PL348325A patent/PL202459B1/pl not_active IP Right Cessation
- 2001-06-27 AU AU54075/01A patent/AU777733B2/en not_active Ceased
-
2002
- 2002-05-02 HK HK02103285.6A patent/HK1041605B/zh not_active IP Right Cessation
-
2004
- 2004-08-30 US US10/929,928 patent/US20050032845A1/en not_active Abandoned
-
2005
- 2005-05-31 JP JP2005158854A patent/JP2005314431A/ja active Pending
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